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US20230000081A1 - Synergistic pesticidal compositions for delivery of pesticidal active ingredients and methods therefor - Google Patents

Synergistic pesticidal compositions for delivery of pesticidal active ingredients and methods therefor Download PDF

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Publication number
US20230000081A1
US20230000081A1 US17/281,210 US201917281210A US2023000081A1 US 20230000081 A1 US20230000081 A1 US 20230000081A1 US 201917281210 A US201917281210 A US 201917281210A US 2023000081 A1 US2023000081 A1 US 2023000081A1
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Prior art keywords
acid
methyl
phenyl
inhibitors
chloro
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US17/281,210
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Karan MANHAS
Annett Rozek
Yuehua He
Costantinos LAMBRINOUDIS
Le Linh BUI
Sadegh SHOKATIAN
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Terramera Inc
0903608 BC Ltd
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Terramera Inc
0903608 BC Ltd
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Priority to US17/281,210 priority Critical patent/US20230000081A1/en
Assigned to TERRAMERA, INC. reassignment TERRAMERA, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HE, YUEHUA, ROZEK, ANNETT, BUI, Le Linh, LAMBRINOUDIS, Costantinos, SHOKATIAN, Sadegh, MANHAS, Karan
Assigned to 0903608 B.C. LTD. reassignment 0903608 B.C. LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TERRAMERA, INC.
Publication of US20230000081A1 publication Critical patent/US20230000081A1/en
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A01N47/14—Di-thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Definitions

  • An embodiment of the present invention is related to compositions and methods for increasing the efficacy of pesticidal compositions. More particularly, some embodiments are related to synergistic pesticidal compositions and methods for delivery of pesticidal active ingredients. Some embodiments of the present invention are directed to compositions and methods for increasing the efficacy of fungicides.
  • Some embodiments of the present invention are directed to compositions and methods for increasing the efficacy of nematicides. Some embodiments of the present invention are directed to compositions and methods for increasing the efficacy of insecticides. Further embodiments of the present invention are directed to methods for enhancing the activity pesticidal active ingredients in pesticidal compositions.
  • Pesticides including fungicides, herbicides, nematicides and insecticides, are important compositions for use in domestic, agricultural, industrial and commercial settings, such as to provide for control of unwanted pests and/or pathogens. Providing for effective pest control is of high importance in many such settings, since pests and/or other pathogens if not controlled can cause loss and or destruction of crops or other plants, or harm to animals, humans or other beneficial or desired organisms.
  • pesticides including fungicides, nematicides and insecticides, or compounds that enhance the efficacy of pesticides, including fungicides, nematicides and insecticides, and for methods of enhancing the efficacy of pesticides including fungicides, nematicides and insecticides, so that pesticides can be used in a more environmentally safe and effective manner.
  • plant pests such as insects, worms, nematodes, fungi, and plant pathogens such as viruses and bacteria, are known to cause significant damage to seeds and ornamental and crop plants.
  • Chemical pesticides have generally been used, but many of these are expensive and potentially toxic to humans, animals, and/or the environment and may persist long after they are applied. Therefore it is typically beneficial to farmers, consumers and the surrounding environment to use the least amount of chemical pesticides as possible, while continuing to control pest growth in order to maximize crop yield. In a growing number of cases, chemical pesticide use has also resulted in growing resistance to certain chemical pesticides by pest organisms, leading to reduced effectiveness, requiring greater doses of pesticidal chemicals, or even failure of certain types of pesticides as viable control agents. As a result, many chemical pesticides are being phased out or otherwise restricted from use.
  • Natural or biologically-derived pesticidal compounds have been proposed for use in place of some chemical pesticides, in order to attempt to reduce the toxicity, health and environmental risks associated with chemical pesticide use.
  • some natural or biologically-derived pesticides have proven less efficacious or consistent in their performance in comparison with competing chemical pesticides, which has limited their adoption as control agents in pesticide markets.
  • synergistic pesticidal compositions that desirably minimize the use of pesticidal agents or pesticidal active ingredients through synergistic efficacy, to provide for desired pest control performance in use.
  • large-scale experimental drug combination studies in non-agricultural fields have found that synergistic combinations of drug pairs are extremely complex and rare, with only a 4-10% probability of finding synergistic drug pairs [Yin et al., PLOS 9:e93960 (2014); Cokol et al., Mol. Systems Biol. 7:544 (2011)].
  • a synergistic pesticidal composition comprising a pesticidal active ingredient; and a C4-C10 unsaturated aliphatic acid (including an unsaturated C6, C7, C8, C9 or C10 aliphatic acid) or an agriculturally compatible salt thereof, wherein the C4-C10 unsaturated aliphatic acid comprises at least one unsaturated C—C bond and wherein a ratio of the concentrations by weight of said pesticidal active ingredient and said C4-C10 unsaturated aliphatic acid or an agriculturally compatible salt thereof is between about 1:15,000 and 15,000:1, and more particularly between about 1:5000 and 5000:1, and further more particularly between about 1:2000 and 2000:1.
  • a synergistic pesticidal composition comprising a pesticidal active ingredient; and a C4-C10 saturated aliphatic acid (including a saturated C4, C5, C6, C7, C8, C9 or C10 aliphatic acid) or an agriculturally compatible salt thereof, wherein a ratio of the concentrations by weight of said pesticidal active ingredient and said C4-C10 saturated aliphatic acid or an agriculturally compatible salt thereof is between about 1:15,000 and 15,000:1, and more particularly between about 1:5000 and 5000:1, and further particularly between about 1:2000 and 2000:1.
  • a synergistic pesticidal composition comprising a pesticidal active ingredient; and a C11 unsaturated or saturated aliphatic acid or an agriculturally compatible salt thereof, wherein a ratio of the concentrations by weight of said pesticidal active ingredient and said C11 unsaturated or saturated aliphatic acid or an agriculturally compatible salt thereof is between about 1:15,000 and 15,000:1, and more particularly between about 1:2000 and 2000:1.
  • a synergistic pesticidal composition comprising a pesticidal active ingredient; and a C12 unsaturated or saturated aliphatic acid or an agriculturally compatible salt thereof, wherein a ratio of the concentrations by weight of said pesticidal active ingredient and said C12 unsaturated or saturated aliphatic acid or an agriculturally compatible salt thereof is between about 1:15,000 and 15,000:1, more particularly between about 1:5000 and 5000:1, and further particularly between about 1:2000 and 2000:1.
  • a method of synergistically enhancing the pesticidal activity of at least one pesticidal active ingredient adapted to control at least one target pest organism comprising: providing at least one pesticidal active ingredient active for said at least one target pest organism; adding a synergistically effective concentration of at least one C4-C10 unsaturated aliphatic acid comprising at least one unsaturated C—C bond, or an agriculturally acceptable salt thereof, to said pesticidal active ingredient to provide a synergistic pesticidal composition; and applying said synergistic pesticidal composition in a pesticidally effective concentration to control said at least one target pest organism.
  • a C4-C10 saturated aliphatic acid or agriculturally compatible salts thereof may be provided to provide the synergistic pesticidal composition.
  • a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof may be provided to provide the synergistic pesticidal composition.
  • a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof may be provided to provide the synergistic pesticidal composition.
  • the synergistic pesticidal composition may comprise a C4-C10 unsaturated or saturated aliphatic acid or a biologically compatible salt thereof, wherein said salt comprises at least one of an agriculturally, aquatic life, or mammal-compatible salt, for example.
  • a C11 unsaturated or saturated aliphatic acid or biologically compatible salt thereof, or a C12 unsaturated or saturated aliphatic acid or biologically compatible salt may be provided.
  • a pesticidal composition comprising: one or more pesticidal agents; and one or more unsaturated C4-C10 aliphatic acids or agriculturally compatible salts thereof having at least one unsaturated C—C bond.
  • a pesticidal composition comprising one or more pesticidal agents at one or more saturated C4-C10 aliphatic acids or agriculturally compatible salts thereof are provided.
  • the one or more saturated or unsaturated C4-C10 aliphatic acids produce a synergistic effect on the pesticidal activity of the pesticidal composition in comparison to the pesticidal activity of the pesticidal agent alone and are present in a respective synergistically active concentration ratio between about 1:15000 and 15000:1, more particularly between about 1:5000 and 5000:1, and further particularly between about 1:2000 and 2000:1.
  • a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof may be provided.
  • a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof may be provided.
  • a method of synergistically enhancing the pesticidal activity of at least one pesticidal active ingredient adapted to control at least one target pest organism comprising: providing at least one pesticidal active ingredient active for said at least one target pest organism; adding a synergistically effective concentration of at least one unsaturated or saturated C4-C10 aliphatic acid or an agriculturally acceptable salt thereof to provide a synergistic pesticidal composition; mixing said synergistic pesticidal composition with at least one formulation component comprising a surfactant to form a synergistic pesticidal concentrate; diluting said synergistic pesticidal concentrate with water to form a synergistic pesticidal emulsion; and applying said synergistic pesticidal emulsion at a pesticidally effective concentration and rate to control said at least one target pest organism.
  • a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof may be provided.
  • the synergistic pesticidal composition may comprise a ratio of the concentrations by weight of said pesticidal active ingredient and said at least one saturated or unsaturated C4-C10 aliphatic acid or agriculturally compatible salts thereof is between about at least one of: 1:20,000 and 20,000:1, 1:15000 and 15000:1, 1:10,000 and 10,000:1, 1:5000 and 5000:1, 1:2500 and 2500:1, 1:2000 and 2000:1, 1:1500 and 1500:1, 1:1000 and 1000, 1:750 and 750:1, 1:500 and 500:1, 1:400 and 400:1, 1:300 and 300:1, 1:250 and 250:1, 1:200 and 200:1, 1:150 and 150:1, 1:100 and 100:1, 1:90 and 90:1, 1:80 and 80:1, 1:70 and 70:1, 1:60 and 60:1, 1:50 and 50:1, 1:40 and 40:1, 1:30 and 30:1, 1:25 and 25:1, 1:20 and 20:1, 1:15 and 15:1, 1:10 and 10:1, 1:9 and
  • the concentration ratios of the pesticidal active ingredient and said at least one C4-C10 saturated or unsaturated aliphatic acid or an agriculturally compatible salt thereof in the synergistic pesticidal composition are advantageously chosen so as to produce a synergistic effect against at least one target pest or pathogen.
  • the concentration ratios of the pesticidal active ingredient(s) and at least one C11 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof in the synergistic pesticidal composition may be advantageously chosen so as to produce a synergistic effect against at least one target pest or pathogen. In some further embodiments, the concentration ratios of the pesticidal active ingredient(s) and at least one C11 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof in the synergistic pesticidal composition may be advantageously chosen so as to produce a synergistic effect against at least one target pest or pathogen.
  • the synergistic pesticidal composition comprises a pesticidal active ingredient, and a C4-C10 unsaturated aliphatic acid which comprises at least one of: a trans-unsaturated C—C bond and a cis-unsaturated C—C bond.
  • the C4-C10 unsaturated aliphatic acid comprises at least one of: a trans-2, trans-3, trans-4, trans-5, trans-6, trans-7, trans-8, and trans-9 unsaturated bond.
  • a synergistic pesticidal composition comprising a pesticidal active ingredient and a C4-C10 unsaturated aliphatic acid comprising at least one of: a cis-2, cis-3, cis-4, cis-5, cis-6, cis-7, cis-8, and cis-9 unsaturated bond.
  • the pesticidal composition comprises a C11 unsaturated aliphatic acid or agriculturally compatible salt thereof, comprising at least one of: a trans-2, trans-3, trans-4, trans-5, trans-6, trans-7, trans-8, trans-9, trans-10, a cis-2, cis-3, cis-4, cis-5, cis-6, cis-7, cis-8, cis-9, and cis-10 unsaturated bond.
  • the pesticidal composition comprises a C12 unsaturated aliphatic acid or agriculturally compatible salt thereof, comprising at least one of: a trans-2, trans-3, trans-4, trans-5, trans-6, trans-7, trans-8, trans-9, trans-10, a cis-2, cis-3, cis-4, cis-5, cis-6, cis-7, cis-8, cis-9, and cis-10 unsaturated bond.
  • the synergistic pesticidal composition may comprise at least one C4-C10 saturated aliphatic acid, such as one or more of hexanoic, heptanoic, octanoic, nonanoic and decanoic acid, for example.
  • the synergistic pesticidal composition may additionally comprise at least one second C4-C10 saturated or unsaturated aliphatic acid.
  • the pesticidal composition may additionally comprise at least one second C11 or C12 unsaturated or saturated aliphatic acid, or agriculturally compatible salt thereof.
  • the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise a naturally occurring aliphatic acid, such as may be present in, or extracted, fractionated or derived from a natural plant or animal material, for example.
  • the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise one or more naturally occurring aliphatic acids provided in a plant extract or fraction thereof.
  • the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise one or more naturally occurring aliphatic acids provided in an animal extract or product, or fraction thereof.
  • the at least one C4-C10 saturated or unsaturated alphatic acid may comprise a naturally occurring aliphatic acid comprised in a plant oil extract, such as one or more of coconut oil, palm oil, palm kernel oil, corn oil, or fractions or extracts therefrom.
  • the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise a naturally occurring aliphatic acid comprised in an animal extract or product, such as one or more of cow's milk, goat's milk, beef tallow, and/or cow or goat butter, or fractions or extracts thereof for example.
  • At least one C4-C10 saturated aliphatic acid may be provided in an extract or fraction of one or more plant oil extract, such as one or more of coconut oil, palm oil, palm kernel oil, corn oil, or fractions or extracts therefrom.
  • the pesticidal composition may comprise at least one C11 or C12 saturated or unsaturated aliphatic acid provided in an extract or fraction of one or more plant or animal materials.
  • the synergistic pesticidal composition exhibits a synergistic inhibition of growth of at least one target pest organism.
  • the synergistic pesticidal composition comprises a pesticidally effective concentration of the pesticidal active ingredient, and the one or more C4-C10 saturated or unsaturated aliphatic acid.
  • the synergistic pesticidal composition comprises a pesticidal active ingredient, and a synergistic concentration of the one or more C4-C10 saturated or unsaturated aliphatic acid.
  • the synergistic pesticidal composition has a FIC Index (fractional inhibitory concentration index value) of less than 1 according to a growth inhibition assay for inhibition of growth of at least one target pest or pathogen organism. In some embodiments, the synergistic pesticidal composition has a FIC Index value of less than 0.75. In a further embodiment, the synergistic pesticidal composition has a FIC Index value of 0.5 or less.
  • the synergistic pesticidal composition has a synergistic efficacy factor, or Synergy Factor (comparing synergistic efficacy relative to expected additive (non-synergistic) efficacy according to the Colby Formula, or Loewe's Formula, or other accepted synergy determination method) of: at least 1.01, and more particularly at least 1.1, and further more particularly at least 1.5, and yet further more particularly at least 2, and more particularly at least 5, and yet more particularly at least 10, for example.
  • the one or more saturated or unsaturated aliphatic acid may comprise a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • the one or more saturated or unsaturated aliphatic acid may comprise a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • the pesticidal active ingredient may comprise at least one of a chemical pesticide and a naturally-derived pesticidal oil or extract.
  • the pesticidal active ingredient may comprise at least one of: a fungicide, nematicide, insecticide, acaricide, herbicide, and bactericide.
  • the synergistic pesticidal composition may comprise one or more C4-C10 saturated or unsaturated aliphatic acid having at least one carboxylic group, and which may be linear or branched.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a linear monocarboxylic acid.
  • the C4-C10 unsaturated aliphatic acid may comprise one or more of cis and trans isomers.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may be unsubstituted or substituted.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a substituent, such as a hydroxy, amino, carbonyl, aldehyde, acetyl, phosphate, or methyl substituent, for example.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise at least one of a 2-, 3-, 4-, 8-, or 10-substituted aliphatic acid.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a hydroxy aliphatic acid. In one particular such embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a 2-hydroxy, 3-hydroxy, or 4-hydroxy aliphatic acid. In one embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise an amino aliphatic acid. In one particular such embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a 3-amino aliphatic acid.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a methyl and/or ethyl substituted aliphatic acid.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise at least one of a 2-methyl, 3-methyl, 4-methyl, 2-ethyl, or 2,2-diethyl substituted aliphatic acid, for example.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise an unsaturated aliphatic acid which may be mono-unsaturated or polyunsaturated, i.e. containing one, two or more unsaturated carbon-carbon (C—C) bonds respectively.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise an unsaturated aliphatic acid with at least one of: a trans-unsaturated C—C bond, a cis-unsaturated C—C bond, and a plurality of conjugated unsaturated C—C bonds.
  • the one or more saturated or unsaturated aliphatic acid may comprise a C11 unsaturated or saturated aliphatic acid.
  • the one or more saturated or unsaturated aliphatic acid may comprise a C12 unsaturated or saturated aliphatic acid.
  • the one or more C4-C10 (including C4, C5, C6, C7, C8, C9 or C10) saturated or unsaturated aliphatic acid may comprise at least one of: a trans-hexenoic acid, a cis-hexenoic acid, a hexa-dienoic acid, a hexynoic acid, a trans-heptenoic acid, a cis-heptenoic acid, a hepta-dienoic acid, a heptynoic acid, a trans-octenoic acid, a cis-octenoic acid, an octa-dienoic acid, an octynoic acid, a trans-nonenoic acid, a cis-nonenoic acid, a nona-dienoic acid, a nonynoic acid, a trans-decenoic acid, a cis-decenoic acid, a deca-
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise at least one of: a trans-hexenoic acid, a cis-hexenoic acid, a hexa-dienoic acid other than 2,4-hexadienoic acid, a hexynoic acid, a trans-heptenoic acid, a cis-heptenoic acid, a hepta-dienoic acid, a heptynoic acid, a trans-octenoic acid, a cis-octenoic acid, an octa-dienoic acid, an octynoic acid, a trans-nonenoic acid, a cis-nonenoic acid, a nona-dienoic acid, a nonynoic acid, a trans-decenoic acid, a cis-decenoic acid, a deca-dienoic acid, and a
  • the one or more unsaturated aliphatic acid may comprise at least one of a C11 or C12 unsaturated aliphatic acid, such as a cis-undecenoic, trans-undecanoic, cis-dodecenoic, trans-dodecenoic, undeca-dienoic, dodeca-dienoic, undecynoic, or dodecynoic acid, for example.
  • a C11 or C12 unsaturated aliphatic acid such as a cis-undecenoic, trans-undecanoic, cis-dodecenoic, trans-dodecenoic, undeca-dienoic, dodeca-dienoic, undecynoic, or dodecynoic acid, for example.
  • the one or more C4-C10 (including C4, C5, C6, C7, C8, C9 or C10) saturated or unsaturated aliphatic acid may comprise at least one of: hexanoic, heptanoic, octanoic, nonanoic and decanoic acid. In some embodiments, the one or more saturated or unsaturated aliphatic acid may comprise at least one of undecanoic or dodecanoic acid.
  • the synergistic pesticidal composition may comprise one or more agriculturally compatible or acceptable salts of a one or more C4-C10 saturated or unsaturated aliphatic acid.
  • such agriculturally compatible or acceptable salts may comprise one or more of potassium, sodium, calcium, aluminum, other suitable metal salts, ammonium, and other agriculturally acceptable salts of one or more C4-C10 saturated or unsaturated aliphatic acids, for example.
  • the synergistic pesticidal composition may comprise one or more C4-C10 saturated or unsaturated aliphatic acid or a biologically compatible salt thereof, wherein said salt comprises at least one of an agriculturally, aquatic life, or mammal-compatible salt, for example.
  • the pesticidal composition may comprise one or more agriculturally compatible or acceptable salts of one or one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • the synergistic pesticidal composition may comprise a pesticidal active ingredient and a one or more C4-C10 saturated or unsaturated aliphatic acid, wherein the C4-C10 unsaturated aliphatic acid comprises at least one unsaturated C—C bond and wherein a ratio of the concentrations of said pesticidal active ingredient and said C4-C10 unsaturated aliphatic acid is between about 1:15000 and 15000:1, more particularly between about 1:5000 and 5000:1, and further particularly between about 1:2000 and 2000:1.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may exclude agriculturally acceptable salts or other salt forms of the one or more C4-C10 saturated or unsaturated aliphatic acids.
  • the synergistic pesticidal composition may exclude such salts for desired applications for which the acid forms of the one or more C4-C10 saturated or unsaturated aliphatic acids may be preferred.
  • the pesticidal composition may comprise one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • the synergistic pesticidal composition may comprise a pesticidal active ingredient and at least one C4-C10 saturated aliphatic acid, such as at least one of hexanoic, heptanoic, octanoic, nonanoic and decanoic acid, for example.
  • the synergistic pesticidal composition may comprise a pesticidal active ingredient and at least one C4-C10 unsaturated aliphatic acid but explicitly excluding 2,4-hexadienoic acid.
  • the one or more saturated or unsaturated aliphatic acid may comprise a C11 unsaturated or saturated aliphatic acid.
  • the one or more saturated or unsaturated aliphatic acid may comprise a C12 unsaturated or saturated aliphatic acid.
  • a synergistic pesticidal composition may comprise at least one C4-C10 saturated or unsaturated aliphatic acid and at least one pesticidal active ingredient selected from the list comprising:
  • the synergistic pesticidal composition may comprise one or more pesticidal active ingredient, such as selected from the list above, and one or more C11 unsaturated or saturated aliphatic acid or agriculturally acceptable salt thereof. In some further such embodiments, the synergistic pesticidal composition may comprise one or more pesticidal active ingredient, such as selected from the list above, and one or more C12 unsaturated or saturated aliphatic acid or agriculturally acceptable salt thereof.
  • synergistic pesticidal compositions may be provided, where the pesticidal active ingredient comprises at least one pesticidal natural oil selected from: neem oil, karanja oil, clove oil, clove leaf oil, peppermint oil, spearmint oil, mint oil, cinnamon oil, thyme oil, oregano oil, rosemary oil, geranium oil, lime oil, lavender oil, anise oil, lemongrass oil, tea tree oil, apricot kernel oil, bergamot oil, carrot seed oil, cedar leaf oil, citronella oil, clove bud oil, coriander oil, coconut oil, eucalyptus oil, evening primrose oil, fennel oil, ginger oil, grapefruit oil, nootkatone(+), grapeseed oil, lavender oil, marjoram oil, pine oil, scotch pine oil, and/or garlic oil and/or components, derivatives and/or extracts of one or more pesticidal natural oil, or a combination thereof.
  • pesticidal natural oil selected from
  • synergistic pesticidal compositions may be provided which comprise additional active components other than the principal one or more pesticidal active ingredients, wherein such additional active components may comprise one or more additional efficacies and/or synergistic effects on the pesticidal efficacy of the composition, such as but not limited to adjuvants, synergists, agonists, activators, or combinations thereof, for example.
  • additional active components may optionally comprise naturally occurring compounds or extracts or derivatives thereof.
  • the pesticidal active ingredient may comprise at least one organic, certified organic, US Department of Agriculture (“USDA”) National Organic Program compliant (“NOP-compliant”) such as may be included in the US Environmental Protection Agency FIFRA 25b, list of ingredients published dated December 2015 by the US EPA entitled “Active Ingredients Eligible for Minimum Risk Pesticide Products”, the US EPA FIFRA 4a list published August 2004 entitled “List 4A—Minimal Risk Inert Ingredients” or the US EPA FIFRA 4b list published August 2004 entitled “List 4B—Other ingredients for which EPA has sufficient information”, for example, Organic Materials Review Institute listed (“OMRI-listed”) or natural pesticidal active ingredient, for example.
  • USDA organic, certified organic, US Department of Agriculture
  • NOP-compliant National Organic Program compliant
  • the pesticidal active ingredient may comprise at least one of: neem oil, karanja oil and extracts or derivatives thereof.
  • the pesticidal active ingredient may comprise at least one extract or active component of neem oil or karanja oil, such as but not limited to: azadirachtin, azadiradione, azadirone, nimbin, nimbidin, salannin, deacetylsalannin, salannol, maliantriol, gedunin, karanjin, pongamol, or derivatives thereof, for example.
  • FIG. 1 illustrates general carbonyl alkene structures (1), (2) and (3) associated with an exemplary C4-C10 unsaturated aliphatic acid, or agriculturally acceptable salt thereof, according to an embodiment of the present disclosure.
  • FIG. 2 illustrates an exemplary 96 well microtiter plate showing a color transition of a resazurin dye between colors indicating absence and presence of growth of a representative pest or pathogen, in accordance with a synergistic growth inhibition assay according to an embodiment of the present disclosure.
  • FIGS. 3 - 5 illustrate the observed survival rate (percent of original insects still surviving) for Trichoplusia ni (cabbage looper caterpillar) over time for in-vitro testing on a modified McMorran artificial diet to which treatments of Pylon® insecticide (containing chlorfenapyr as the pesticidal active ingredient) and exemplary unsaturated aliphatic acids (and salts) alone are shown in comparison with the corresponding survival rates for treatments with a synergistic pesticidal composition combining Pylon® insecticide with each of the exemplary unsaturated aliphatic acids (and salts) at three concentrations (shown in FIGS. 3 , 4 , and 5 respectively), according to an embodiment of the present invention.
  • Pylon® insecticide containing chlorfenapyr as the pesticidal active ingredient
  • exemplary unsaturated aliphatic acids (and salts) alone are shown in comparison with the corresponding survival rates for treatments with a synergistic pesticidal composition combining Pylon® insecticide with each
  • references to a range of 90-100% includes 91%, 92%, 93%, 94%, 95%, 95%, 97%, etc., as well as 91.1%, 91.2%, 91.3%, 91.4%, 91.5%, etc., 92.1%, 92.2%, 92.3%, 92.4%, 92.5%, etc., and so forth.
  • plant embraces individual plants or plant varieties of any type of plants, in particular agricultural, silvicultural and ornamental plants.
  • Pests are understood to refer to organisms, e.g., including pathogens, that negatively affect a host or other organism—such as a plant or an animal—by colonizing, damaging, attacking, competing with them for nutrients, infesting or infecting them, as well as undesired organisms that infest human structures, dwellings, living spaces or foodstuffs. Pests include but are not limited to fungi, weeds, nematodes, acari, and arthropods, including insects, arachnids and cockroaches. It is understood that the terms “pest” or “pests” or grammatical equivalents thereof can refer to organisms that have negative effects by infesting plants and seeds, and commodities such as stored grain.
  • control or “controlling” are meant to include, but are not limited to, any killing, inhibiting, growth regulating, or pestistatic (inhibiting or otherwise interfering with the normal life cycle of the pest) activities of a composition against a given pest. These terms include for example sterilizing activities which prevent the production or normal development of seeds, ova, sperm or spores, cause death of seeds, sperm, ova or spores, or otherwise cause severe injury to the genetic material.
  • control or “controlling” include preventing larvae from developing into mature progeny, modulating the emergence of pests from eggs including preventing eclosion, degrading the egg material, suffocation, interfering with mycelial growth, reducing gut motility, inhibiting the formation of chitin, disrupting mating or sexual communication, preventing feeding (antifeedant) activity, and interfering with location of hosts, mates or nutrient-sources.
  • pesticide includes fungicides, herbicides, nematicides, insecticides and the like.
  • pesticide encompasses, but is not limited to, naturally occurring compounds as well as so-called “synthetic chemical pesticides” having structures or formulations that are not naturally occurring, where pesticides may be obtained by various means including, but not limited to, extraction from biological sources, chemical synthesis of the compound, and chemical modification of naturally occurring compounds obtained from biological sources.
  • insecticidal and “acaridical” or “aphicidal” or grammatical equivalents thereof, are understood to refer to substances having pesticidal activity against organisms encompassed by the taxonomical classification of root term and also to refer to substances having pesticidal activity against organisms encompassed by colloquial uses of the root term, where those colloquial uses may not strictly follow taxonomical classifications.
  • insecticidal is understood to refer to substances having pesticidal activity against organisms generally known as insects of the phylum Arthropoda, class Insecta.
  • the term is also understood to refer to substances having pesticidal activity against other organisms that are colloquially referred to as “insects” or “bugs” encompassed by the phylum Arthropoda, although the organisms may be classified in a taxonomic class different from the class Insecta.
  • insecticidal can be used to refer to substances having activity against arachnids (class Arachnida), in particular mites (subclass Acari/Acarina), in view of the colloquial use of the term “insect.”
  • acaridical is understood to refer to substances having pesticidal activity against mites (Acari/Acarina) of the phylum Arthropoda, class Arachnida, subclass Acari/Acarina.
  • aphicidal is understood to refer to substances having pesticidal activity against aphids (Aphididae) of the phylum Arthopoda, class Insecta, family Aphididae. It is understood that all these terms are encompassed by the term “pesticidal” or “pesticide” or grammatical equivalents. It is understood that these terms are not necessarily mutually exclusive, such that substances known as “insecticides” can have pesticidal activity against organisms of any family of the class Insecta, including aphids, and organisms that are encompassed by other colloquial uses of the term “insect” or “bug” including arachnids and mites. It is understood that “insecticides” can also be known as acaricides if they have pesticidal activity against mites, or aphicides if they have pesticidal activity against aphids.
  • control or “controlling” or grammatical equivalents thereof, are understood to encompass any pesticidal (killing) activities or pestistatic (inhibiting, repelling, deterring, and generally interfering with pest functions to prevent the damage to the host plant) activities of a pesticidal composition against a given pest.
  • control or “controlling” or grammatical equivalents thereof, not only include killing, but also include such activities as repelling, deterring, inhibiting or killing egg development or hatching, inhibiting maturation or development, and chemisterilization of larvae or adults.
  • Repellant or deterrent activities may be the result of compounds that are poisonous, mildly toxic, or non-poisonous to pests, or may act as pheromones in the environment.
  • the term “pesticidally effective amount” generally means the amount of the inventive mixtures or of compositions comprising the mixtures needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target pest organism.
  • the pesticidally effective amount can vary for the various mixtures/compositions used in the invention.
  • a pesticidally effective amount of the mixtures/compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mod+e of application, and the like.
  • a synergistic pesticidal composition comprises a C4-C10 unsaturated aliphatic acid (or agriculturally acceptable salt thereof), the and at least one pesticidal active ingredient.
  • the effective dose of the pesticidal active ingredient when used in combination with the one or more C4-C10 saturated or unsaturated aliphatic acid is lower than the effective dose of the pesticidal active ingredient when used alone (i.e. a smaller amount of pesticidal active can still control pests when used in a synergistic composition together with the one or more C4-C10 saturated or unsaturated aliphatic acid).
  • a pesticidal active ingredient that is not effective against a particular species of pest can be made effective against that particular species when used in a synergistic composition together with one or more C4-C10 saturated or unsaturated aliphatic acid.
  • the pesticidal composition may comprise a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • the pesticidal composition may comprise a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • the one or more C4-C10 saturated or unsaturated aliphatic acids act as cell permeabilizing agents, and when combined with a suitable pesticidal active ingredient, may desirably facilitate the entry of the pesticidal active ingredient into the cells of a target pest or pathogen, thereby desirably providing for a synergistic activity of such a synergistic pesticidal composition.
  • eukaryotic cell membranes including for example fungal cell membranes and the cell membranes of insects and nematodes are biochemically similar in that they all comprise a lipid bilayer which is comprised of phospholipids, glycolipids and sterols, as well as a large number of proteins (Cooper & Hausmann 2013).
  • the amphipathic structure of the lipid bilayer and the polarity of membrane proteins restricts passage of extracellular compounds across the membrane and allows compartmentalization of internal organelles from the intracellular environment.
  • the one or more C4-C10 saturated or unsaturated aliphatic acids will act as cell permeabilizing agents, and when combined with a suitable pesticidal active ingredient may desirably act to enhance the entry of the active ingredient (such as but not limited to fungicidal, insecticidal, acaricidal, molluscicidal, bactericidal and nematicidal actives) into the cells and/or into the intracellular organelles or intracellular bodies of a target pest or pathogen (such as but not limited to fungi, insects, acari, mollusks, bacteria and nematodes, respectively), for example.
  • a target pest or pathogen such as but not limited to fungi, insects, acari, mollusks, bacteria and nematodes, respectively
  • the size and/or polarity of many pesticidal molecules prevents and/or limits the pesticidal active ingredient from crossing the cellular membrane, but that the addition of one or more C4-C10 saturated or unsaturated aliphatic acid in accordance with some embodiments of the present disclosure may desirably compromise or provide for the disturbance of the pest cell membrane's lipid bilayer integrity and protein organization such as to create membrane gaps, and/or increase the membrane fluidity, such as to allow the pesticidal active to more effectively enter the cell and/or intracellular organelles of the pest cells, for example.
  • the pesticidal composition may comprise a C11 unsaturated aliphatic acid or agriculturally compatible salt thereof.
  • the pesticidal composition may comprise a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • the one or more C4-C10 saturated or unsaturated aliphatic acids, or agriculturally acceptable salts thereof (and in some additional embodiments, alternatively a C11 or C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof).
  • the pesticidal composition may comprise a C12 unsaturated aliphatic acid or agriculturally compatible salt thereof according to some embodiments of the present disclosure act as at least one of a potentiator, synergist, adjuvant and/or agonist when combined with a suitable pesticidal active ingredient, thereby desirably providing for a synergistic activity of such a synergistic pesticidal composition against a target pest or pathogen.
  • a synergistic pesticidal composition accordingly to the present invention comprises one or more C4-C10 saturated or unsaturated aliphatic acid, or agriculturally acceptable salts thereof (and in some additional embodiments, alternatively a C11 or C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof), as an exemplary cell permeabilizing agent, in combination with a pesticide.
  • the synergistic composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof), as an exemplary cell permeabilizing agent, in combination with a fungicide.
  • the synergistic composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof), as an exemplary cell permeabilizing agent, in combination with a nematicide. In some embodiments, the synergistic composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof), as an exemplary cell permeabilizing agent, in combination with an insecticide.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may act as a cellular membrane delivery agent, so as to improve the entry of and/or bioavailability or systemic distribution of a pesticidal active ingredient within a target pest cell and/or within a pest intracellular organelle, such by facilitating the pesticidal active ingredient in passing into the mitochondria of the pest cells, for example.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may further provide for synergistic interaction with one or more additional compounds provided as part of the pesticidal composition, such as an additional one or more C4-C10 saturated aliphatic acid, or one or more C4-C10 unsaturated aliphatic acid, or one or more additional active ingredients or adjuvants, so as to provide for synergistic enhancement of a pesticidal effect provided by the at least one pesticidal active ingredient, for example.
  • additional compounds provided as part of the pesticidal composition such as an additional one or more C4-C10 saturated aliphatic acid, or one or more C4-C10 unsaturated aliphatic acid, or one or more additional active ingredients or adjuvants, so as to provide for synergistic enhancement of a pesticidal effect provided by the at least one pesticidal active ingredient, for example.
  • the one or more C4-C10 saturated or unsaturated aliphatic acids (or agriculturally acceptable salts thereof) act as at least one of a potentiator, synergist, adjuvant and/or agonist when combined with a suitable pesticidal ingredient, thereby desirably providing for a synergistic activity of such a synergistic pesticidal composition against a target pest or pathogen.
  • a synergistic pesticidal composition may alternatively comprise a C11 or C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • the one or more C4-C10 saturated or unsaturated aliphatic acids act to compromise or alter the integrity of the lipid bilayer and protein organization of cellular membranes in target pest organisms. Further, it is also believed that in some embodiments one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action that is dependent upon interaction with one or more components of the cellular membrane of a target pest.
  • one or more C4-C10 saturated or unsaturated aliphatic acids may be particularly adapted for combining to form a synergistic pesticidal composition, demonstrating synergistic efficacy, with pesticidal actives which have a mode of action dependent on interaction with a cellular membrane protein.
  • the cellular membrane protein may comprise one or more cytochrome complexes, such as a cytochrome bel complex or a cytochrome p450 complex, for example.
  • synergistic pesticidal compositions may desirably be selected to comprise one or more C4-C10 saturated or unsaturated aliphatic acids, and one or more pesticidal active having a pesticidal mode of action that is dependent upon interaction with one or more components of the cellular membrane of a target pest, such as a cellular membrane protein, for example.
  • one or more C11 or C12 saturated or unsaturated aliphatic acids is provided in combination with one or more pesticidal active having a pesticidal mode of action that is dependent upon interaction with one or more components of the cellular membrane of a target pest, such as a cellular membrane protein, for example.
  • one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by inhibiting one or more receptor sites) the cellular membrane cytochrome be 1 complex (also known as the cytochrome complex III), such as fungicidal actives collectively referred to as Group 11 actives by the Fungicide Resistance Action Committee (FRAC), including e.g.
  • FRAC Fungicide Resistance Action Committee
  • azoxystrobin coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, mandestrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim-methyl trifloxystrobin, dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, or pyribencar.
  • a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with the cellular cytochrome bel complex, such as a strobilurin pesticidal active.
  • the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by inhibiting one or more receptor sites) the cellular membrane cytochrome p450 complex, such as to inhibit sterol biosynthesis, as is the case with exemplary fungicidal actives collectively referred to as FRAC Group 3 actives, including e.g.
  • a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with the cellular cytochrome p450 complex, such as an azole or triazole pesticidal active, for example.
  • the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by inhibiting one or more receptor sites) the cellular membrane, such as to uncouple oxidative phosphorylation, as is the case with exemplary insecticidal actives collectively referred to as Group 13 actives by the Insecticide Resistance Action Committee (IRAC), including e.g. quinoxyfen or proquinazid.
  • IRAC Insecticide Resistance Action Committee
  • a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with the cellular membrane, such as a pyrrole insecticidal active, an example of which is chlorfenapyr.
  • the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by disrupting and/or allosterically modulating one or more receptor sites) the cellular membrane, such as to disrupt one or more nicotinic acetylcholine receptor sites (such as Site 1), as is the case with exemplary insecticidal actives collectively referred to as Group 5 actives by the Insecticide Resistance Action Committee (IRAC).
  • IRAC Insecticide Resistance Action Committee
  • Such IRAC Group 5 actives include, for example: spinosyn (including but not limited to spinosyns A, D, B, C, E, F, G, H, J, and other spinosyn isolates from Saccharopolyspora spinosa culture), spinosad (comprising primarily spinsyns A and D), and derivatives or substituents thereof (including but not limited to tetracyclic and pentacyclic spinosyn derivatives, aziridine spinosyn derivatives, C-5,6 and/or C-13,14 substituted spinosyn derivatives); spinetoram (including but not limited to XDE-175-J, XDE-175-L or other O-ethyl substituted spinosyn derivatives); butenyl-spinosyn and derivatives or substituents thereof (such as isolates from Saccharopolyspora pogona culture).
  • spinosyn including but not limited to spinosyns A,
  • a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with the cellular membrane, such as a spinosyn or spinosyn derivative insecticidal active, examples of which may include Spinosad and spinetoram.
  • the synergistic pesticidal composition may comprise one or more C11 or C12 saturated or unsaturated aliphatic acids, substituents, or salts thereof.
  • one or more C4-C10 saturated or unsaturated aliphatic acids act to compromise or alter the integrity of the lipid bilayer and protein organization of cellular membranes in target pest organisms, and by so doing are effective to increase at least one of the fluidity and permeability of a cellular membrane of a target pest organism, which may desirably increase permeability and/or transport of a pesticidal active through the cellular membrane, for example.
  • one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action that is dependent upon transport across one or more cellular membrane of a target pest, such as to interact with a target site inside a cell or an intracellular organelle of the target pest.
  • a synergistic pesticidal composition according to an embodiment of the present invention may comprise one or more C4-C10 saturated or unsaturated aliphatic acid, and one or more pesticidal active having a mode of action dependent on transport across a cellular membrane.
  • synergistic pesticidal compositions according to some embodiments of the present invention may desirably be selected to comprise one or more C4-C10 saturated or unsaturated aliphatic acids, and one or more pesticidal active having a pesticidal mode of action that is dependent upon interaction with a target site within a cell or intracellular organelle of a target pest, such as a cellular membrane protein, for example.
  • the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by inhibiting one or more receptors) at a target site across a cellular membrane of a target pest, such as fungicidal actives collectively referred to as FRAC Group 9 and Group 12 actives, for example, including e.g. cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil or fludioxonil.
  • FRAC Group 9 and Group 12 actives for example, including e.g. cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil or fludioxonil.
  • a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with a target site within a cellular membrane of a target pest, such as one or more of an anilinopyrimidine such as cyprodinil, and a phenylpyrrole such as fludioxonil, for example.
  • the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • one or more C4-C10 saturated or unsaturated aliphatic acids act to compromise or alter the integrity of the lipid bilayer and protein organization of cellular membranes in target pest organisms, and by so doing are effective to increase at least one of the fluidity and permeability of a cellular membrane of a target pest organism, which may desirably increase permeability and/or transport of a pesticidal active through the cellular membrane, for example.
  • one or more C4-C10 unsaturated aliphatic acids having unsaturated C—C bonds at one or more of the second (2-), third (3-) and terminal ((n ⁇ 1)-) locations in the aliphatic acid carbon chain may be desirably adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives.
  • one or more C4-C10 aliphatic acids comprising an unsaturated C—C bond at one or more of the 2-,3- and (n ⁇ 1)-locations may desirably be adapted for forming synergistic pesticidal compositions in combination with one or more pesticidal active having a pesticidal mode of action that is dependent upon interaction with a cellular membrane component of a target pest, or dependent upon transport across one or more cellular membrane of a target pest (such as to interact with a target site inside a cell or an intracellular organelle of the target pest).
  • a synergistic pesticidal composition may comprise one or more C4-C10 unsaturated aliphatic acid having an unsaturated C—C bond at one or more of the 2-, 3- and terminal ((n ⁇ 1)-) locations in the aliphatic acid carbon chain, and one or more pesticidal active having a mode of action dependent on interaction with a target pest cellular membrane component, or on transport across a target pest cellular membrane.
  • the synergistic pesticidal composition comprises one or more C11 or C12 unsaturated aliphatic acids having an unsaturated C—C bond at one or more of the 2-, 3- and terminal ((n ⁇ 1)-).
  • the one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises an aliphatic carbonyl alkene. In some embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises at least one C4-C10 unsaturated aliphatic acid having at least one carboxylic group and at least one unsaturated C—C bond. In another embodiment, the C4-C10 unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises at least two C4-C10 unsaturated aliphatic acids having at least one carboxylic group and at least one unsaturated C—C bond.
  • the C4-C10 unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises at least one carboxylic acid group and at least one of a double or triple C—C bond.
  • a synergistic pesticidal composition comprising at least one pesticidal active ingredient, and at least one C4-C10 unsaturated aliphatic acid (or agriculturally acceptable salt thereof) having at least one carboxylic acid group and at least one unsaturated C—C bond, in combination with at least one C4-C10 saturated aliphatic acid (or agriculturally acceptable salt thereof).
  • the C4-C10 saturated or unsaturated aliphatic acid may be provided as a plant extract or oil, or fraction thereof, containing the at least one C4-C10 saturated or unsaturated aliphatic acid, for example, or in further embodiments, containing the one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises an aliphatic carbonyl alkene having one of the general structures (1), (2) or (3), as shown in FIG. 1 .
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may additionally comprise a C11 or C12 saturated or unsaturated aliphatic acid, and may comprise an aliphatic carbonyl alkene having one of the general structures (1), (2) or (3) as shown in FIG. 1 .
  • the C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid may additionally comprise at least one substituent selected from the list comprising: hydroxy, alkyl and amino substituents.
  • the at least one substituent may comprise at least one of: 2-hydroxy, 3-hydroxy, 4-hydroxy, 8-hydroxy, 10-hydroxy, 12-hydroxy, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2,2-diethyl, 2-amino, 3-amino, and 4-amino substituents, for example.
  • the C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid may comprise an agriculturally acceptable salt form of any of the above-mentioned aliphatic acids.
  • the composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) and a fungicidal active ingredient.
  • the effective dose of the fungicidal active ingredient when used in combination with the one or more C4-C10 saturated or unsaturated aliphatic acid is lower than the effective dose of the fungicidal active ingredient when used alone (i.e.
  • a smaller amount of fungicidal active can still control fungi when used in a composition together with the one or more C4-C10 saturated or unsaturated aliphatic acid).
  • a fungicidal active ingredient that is not effective against a particular species of fungi can be made effective against that particular species when used in a composition together with one or more C4-C10 saturated or unsaturated aliphatic acid, or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • the composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) and a nematicidal active ingredient.
  • the effective dose of the nematicidal active ingredient when used in combination with the one or more C4-C10 saturated or unsaturated aliphatic acid is lower than the effective dose of the nematicidal active ingredient when used alone (i.e. a smaller amount of nematicidal active can still control nematodes when used in a composition together with the one or more C4-C10 saturated or unsaturated aliphatic acid).
  • a nematicidal active ingredient that is not effective against a particular species of nematode can be made effective against that particular species when used in a composition together with one or more C4-C10 saturated or unsaturated aliphatic acid, or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • the composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) and an insecticidal active ingredient.
  • the effective dose of the insecticidal active ingredient when used in combination with the one or more C4-C10 saturated or unsaturated aliphatic acid is lower than the effective dose of the insecticidal active ingredient when used alone (i.e. a smaller amount of insecticidal active can still control insects, to an exemplary desired degree of control, when used in a composition together with the one or more C4-C10 saturated or unsaturated aliphatic acid).
  • the aliphatic acid may further comprise one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • an insecticidal active ingredient that is not effective against a particular species of insect can be made effective against that particular species when used in a composition together with one or more C4-C10 saturated or unsaturated aliphatic acid, or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • the one or more C4-C10 saturated or unsaturated aliphatic acid may desirably provide for a synergistic increased efficacy of at least one of an acaricidal, molluscicidal, bactericidal or virucidal active ingredient such that the composition is pesticidally effective against one or more of an acari, mollusk, bacterial or viral pest, for example.
  • a pesticidal composition comprising at least one C4-C10 saturated or unsaturated aliphatic acid (or in some further embodiments at least one C11 or C12 saturated or unsaturated apliphatic acid) and an insecticidal pesticidal active ingredient, comprising at least one nicotinic acetylcholine receptor disruptors.
  • the insecticidal active ingredient may comprise at least one or more of: a spinosyn (including but not limited to spinosyns A, D, B, C, E, F, G, H, J, and other spinosyn isolates from Saccharopolyspora spinosa culture), spinosad (comprising primarily spinsyns A and D), and derivatives or substituents thereof (including but not limited to tetracyclic and pentacyclic spinosyn derivatives, aziridine spinosyn derivatives, C-5,6 and/or C-13,14 substituted spinosyn derivatives); a spinetoram (including but not limited to XDE-175-J and XDE-175-L); and a butenyl-spinosyn and derivatives or substituents thereof (such as isolates from Saccharopolyspora pogona culture).
  • a spinosyn including but not limited to spinosyns A, D, B,
  • a pesticidal composition comprising at least one C4-C10 saturated or unsaturated aliphatic acid (or in some further embodiments at least one C11 or C12 saturated or unsaturated apliphatic acid) and at least one of spinosyn A and spinosyn D.
  • the at least one spinosyn comprises spinosad.
  • the pesticidal composition comprises a synergistic pesticidal composition.
  • the synergistic pesticidal composition desirably provides a synergistic efficacy to control at least one insect pest.
  • a method of reducing a risk of resistance of at least one target pest to at least one pesticidal active ingredient comprising:
  • the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise a naturally occurring aliphatic acid, such as may be present in, or extracted, fractionated or derived from a natural plant or animal material, for example.
  • the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise one or more naturally occurring aliphatic acids provided in a plant extract or fraction thereof.
  • the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise one or more naturally occurring aliphatic acids provided in an animal extract or product, or fraction thereof.
  • the at least one C4-C10 saturated or unsaturated alphatic acid may comprise a naturally occurring aliphatic acid comprised in a plant oil extract, such as one or more of coconut oil, palm oil, palm kernel oil, corn oil, or fractions or extracts therefrom.
  • the at least one C4-C10 saturated or unsaturated alphatic acid may comprise a naturally occurring aliphatic acid comprised in an animal extract or product, such as one or more of cow's milk, goat's milk, beef tallow, and/or cow or goat butter, or fractions or extracts thereof for example.
  • At least one C4-C10 saturated or unsaturated aliphatic acid may be provided as a component of one or more natural plant or animal material, or extract or fraction thereof.
  • at least one C4-C10 saturated aliphatic acid may be provided in an extract or fraction of one or more plant oil extract, such as one or more of coconut oil, palm oil, palm kernel oil, corn oil, or fractions or extracts therefrom.
  • an emulsifier or other surfactant may be used in preparing pesticidal compositions according to aspects of the present disclosure.
  • Suitable surfactants can be selected by one skilled in the art.
  • surfactants that can be used in some embodiments of the present disclosure include, but are not limited to sodium lauryl sulfate, saponin, ethoxylated alcohols, ethoxylated fatty esters, alkoxylated glycols, ethoxylated fatty acids, ethoxylated castor oil, glyceryl oleates, carboxylated alcohols, carboxylic acids, ethoxylated alkylphenols, fatty esters, sodium dodecylsulfide, other natural or synthetic surfactants, and combinations thereof.
  • the surfactant(s) are non-ionic surfactants. In some embodiments, the surfactant(s) are cationic or anionic surfactants. In some embodiments, a surfactant may comprise two or more surface active agents used in combination. The selection of an appropriate surfactant depends upon the relevant applications and conditions of use, and selection of appropriate surfactants are known to those skilled in the art.
  • a pesticidal composition comprises one or more suitable carrier or diluent component.
  • a suitable carrier or diluent component can be selected by one skilled in the art, depending on the particular application desired and the conditions of use of the composition.
  • Commonly used carriers and diluents may include ethanol, isopropanol, isopropyl myristate, other alcohols, water and other inert carriers, such as but not limited to those listed by the EPA as a Minimal Risk Inert Pesticide Ingredients (4A) (the list of ingredients published dated December 2015 by the US EPA FIFRA 4a list published August 2004 entitled “List 4A—Minimal Risk Inert Ingredients”) or, for example, Inert Pesticide Ingredients (4B) (the US EPA FIFRA 4b list published August 2004 entitled “List 4B—Other ingredients for which EPA has sufficient information”) or under EPA regulation 40 CFR 180.950 dated May 24, 2002, each of which is hereby incorporated herein in its entirety for all purposes including for example, citric acid, lactic acid, glycerol, castor oil, benzoic acid, carbonic acid, ethoxylated alcohols, ethoxylated amides, glycerides, benzene, but
  • a method of enhancing the efficacy of a pesticide is provided. In one aspect, a method of enhancing the efficacy of a fungicide is provided. In another aspect, a method of enhancing the efficacy of a nematicide is provided. In a further aspect, a method of enhancing the efficacy of an insecticide is provided.
  • the method comprises providing a synergistic pesticidal composition comprising a pesticidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid (or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid) and exposing a pest to the resulting synergistic composition.
  • the at least one C4-C10 saturated or unsaturated aliphatic acid may desirably be functional as a cell permeabilizing or cell membrane disturbing agent.
  • the method comprises providing a fungicidal composition comprising a fungicidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid and exposing a fungus to the resulting synergistic composition.
  • the method comprises providing a nematicidal composition comprising a nematicidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid and exposing a nematode to the resulting synergistic composition.
  • the method comprises providing an insecticidal composition comprising an insecticidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid and exposing an insect to the resulting synergistic composition.
  • the at least one C4-C10 saturated or unsaturated aliphatic acid (or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid) provided in a pesticidal composition comprises an unsaturated aliphatic carbonyl alkene.
  • the at least one C4-C10 unsaturated aliphatic acid may desirably be functional as a cell permeabilizing or cell membrane disturbing agent.
  • the cell permeabilizing agent comprises a carbonyl alkene having the general structure (1), (2) or (3), as shown in FIG. 1 .
  • the cell permeabilizing agent comprises at least one unsaturated aliphatic acid comprising at least one carboxylic group and having at least one unsaturated C—C bond.
  • a method comprises providing a synergistic pesticidal composition comprising a pesticidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid (or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid) which is functional as a cell permeabilizing agent, and exposing a pest to the synergistic pesticidal composition to increase the amount of the pesticidal active ingredient that enters cells of the pest.
  • the pesticidal active is a fungicide and the pest is a fungus, and without being bound by a particular theory, the at least one C4-C10 saturated or unsaturated aliphatic acid cell permeabilizing agent allows the fungicide to pass more easily through the fungal cell walls and membranes, and/or intracellular membranes.
  • the pesticide is a nematicide and the pest is a nematode, and without being bound by a particular theory, the at least one C4-C10 saturated or unsaturated aliphatic acid cell permeabilizing agent allows the nematicide to pass more easily through the nematode cell and intracellular membranes.
  • the pesticide is an insecticide
  • the at least one C4-C10 saturated or unsaturated aliphatic acid cell permeabilizing agent allows the insecticide to pass more easily through insect cuticle, chitin membrane, or cell or intracellular membranes.
  • synergistic pesticidal compositions according to embodiments of the present disclosure can also desirably have further surprising advantageous properties.
  • additional advantageous properties may comprise one or more of: more advantageous degradability in the environment; improved toxicological and/or ecotoxicological behaviour such as reduced aquatic toxicity or toxicity to beneficial insects, for example.
  • synergistic pesticidal composition comprising at least one pesticidal active and one or more C4-C10 saturated or unsaturated aliphatic acid or salt thereof
  • the synergistic pesticidal composition may alternatively comprise at least one pesticidal active and one or more C11 saturated or unsaturated aliphatic acid or salt thereof.
  • synergistic pesticidal composition comprising at least one pesticidal active and one or more C4-C10 saturated or unsaturated aliphatic acid or salt thereof
  • the synergistic pesticidal composition may alternatively comprise at least one pesticidal active and one or more C12 saturated or unsaturated aliphatic acid or salt thereof.
  • the combination of at least one C4-C10 saturated or unsaturated aliphatic acid (and in some embodiments alternatively at least one C11 or C12 saturated or unsaturated aliphatic acid) and a pesticidal active ingredient produces a synergistic pesticidal composition demonstrating a synergistic pesticidal effect.
  • the synergistic action between the pesticidal active ingredient, and the at least one C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid components of the pesticidal compositions according to embodiments of the present disclosure was tested using a Synergistic Growth Inhibition Assay, which is derived from and related to a checkerboard assay as is known in the art for testing of combinations of antimicrobial agents.
  • multiple dilutions of combinations of pesticidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid agents are tested in individual cells for inhibitory activity against a target pest or pathogenic organism.
  • the combinations of pesticidal active ingredient and C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents may preferably be tested in decreasing concentrations.
  • the combinations of pesticidal active ingredient and C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents may be tested in increasing concentrations.
  • the Synergistic Growth Inhibition Assay then comprises rows which each contain progressively decreasing concentrations of the pesticidal active ingredient and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents to test for the MIC of the agents in combination at which growth of the target pest or pathogen is inhibited.
  • each well of the microtiter plate is a unique combination of the two agents, at which inhibitory efficacy of the combination against the target pest or pathogen can be determined.
  • a method of determining and quantifying synergistic efficacy is by calculation of the “Fractional Inhibitory Concentration Index” or FIC index, as is known in the art for determining synergy between two antibiotic agents (see for example M. J. Hall et al., “The fractional inhibitory concentration (FIC) index as a measure of synergy”, J Antimicrob Chem., 11 (5):427-433, 1983, for example).
  • FIC index Fractional Inhibitory Concentration Index
  • the FIC index is calculated from the lowest concentration of the pesticidal active ingredient and one or more C4-C10 saturated or unsaturated aliphatic acid agents necessary to inhibit growth of a target pest or pathogen.
  • the FIC of each component is derived by dividing the concentration of the agent present in that well of the microtiter plate by the minimal inhibitory concentration (MIC) needed of that agent alone to inhibit growth of the target pest or pathogen.
  • the FIC index is then the sum of these values for both agents in that well of the microtiter plate.
  • the FIC index is calculated for each row as follows:
  • MIC a , MIC b are the minimal inhibitory concentration (MIC) of compounds A and B, respectively, when combined in the mixture of the composition
  • MIC A , MIC B are the MIC of compounds A and B, respectively, when used alone.
  • Fractional inhibitory concentration indices may then used as measure of synergy.
  • FIC index ⁇ 1 the lowest FIC index obtained in a microtiter plate in this way is less than 1 (FIC index ⁇ 1)
  • the combination of the pesticidal active ingredient and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents exhibits synergism, and indicates a synergistic pesticidal composition.
  • FIC index is equal to 1
  • the combination is additive.
  • FIC index values of greater than 4 are considered to exhibit antagonism.
  • an FIC index of 0.5 may correspond to a synergistic pesticidal composition comprising a pesticidal agent at 1 ⁇ 4 of its individual MIC, and one or more (or alternatively C11 or C12) C4-C10 saturated or unsaturated aliphatic acid agent at 1 ⁇ 4 of its individual MIC.
  • the exemplary Synergistic Growth Inhibition Assay was conducted starting with an initial composition comprising a pesticidal active ingredient agent (compound A) at its individual MIC and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent (compound B) at its individual MIC in the first well of a row on a 96 well microtiter plate. Then, serial dilutions of these initial compositions in successive wells in the row of the microtiter plate were used to assay the pesticidal composition under the same conditions to determine the concentration of the composition combining the two agents corresponding to the microtiter well in which growth inhibition of the target pest or organism ceases.
  • a pesticidal active ingredient agent compound A
  • each individual pesticidal active ingredient agent (compound A) and each of the one or more C4-C10 saturated or unsaturated aliphatic acid agent (as compound B) were determined in parallel with the compositions combining the two agents.
  • Fusarium oxysporum was used as a representative pest organism or pathogen to determine synergy in pesticidal compositions comprising a pesticidal active ingredient agent (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent (compound B).
  • Resazurin dye also known as Alamar blue dye
  • an optical or visual examination of the microtiter well may also be made to additionally determine the presence of growth or inhibition of growth of the Fusarium oxysporum.
  • Botrytis cinerea was used as a representative pest organism or pathogen to determine synergy in pesticidal compositions comprising a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent (compound B).
  • a pesticidal active ingredient compound A
  • C4-C10 or alternatively C11 or C12 saturated or unsaturated aliphatic acid agent
  • Resazurin was used as an indicator of growth or inhibition of growth of Botrytis cinerea in the exemplary Synergistic Growth Inhibition Assay.
  • an optical or visual examination of the microtiter well may also be made to additionally determine the presence of growth or inhibition of growth of the Botrytis cinerea.
  • Sclerotinia sclerotiorum was used as a representative pest organism or pathogen to determine synergy in pesticidal compositions comprising a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent (compound B).
  • a pesticidal active ingredient compound A
  • C4-C10 or alternatively C11 or C12 saturated or unsaturated aliphatic acid agent
  • Resazurin was used as an indicator of growth or inhibition of growth of Sclerotinia sclerotiorum in the exemplary Synergistic Growth Inhibition Assay.
  • an optical or visual examination of the microtiter well may also be made to additionally determine the presence of growth or inhibition of growth of the Sclerotinia sclerotiorum.
  • suitable representative pest or pathogen organisms may be used to determine synergy of combinations of pesticidal active ingredient agents and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents in accordance with embodiments of the present disclosure.
  • C4-C10 or alternatively C11 or C12 saturated or unsaturated aliphatic acid agents
  • other representative fungal pathogens may be used, such as but not limited to Leptosphaeria maculans, Sclerotinia spp. and Verticillium spp.
  • suitable non-fungal representative pests or pathogens may be used, such as insect, acari, nematode, bacterial, viral, mollusc or other pests or pathogens suitable for use in an MIC growth inhibition assay test method.
  • a culture of the representative fungal pathogen namely Fusarium oxysporum, Botrytis cinerea , or Sclerotinia sclerotiorum , for example, is grown to exponential phase in potato dextrose broth (PDB).
  • PDB potato dextrose broth
  • a 20 uL aliquot of homogenized mycelium from the culture is transferred to a well of a 96 well microtiter plate, and incubated for a period between 1 day and 7 days (depending on the pathogen and the particular assay reagents, as noted in the example descriptions below) with 180 uL of the test solution comprising the pesticidal and aliphatic acid agents in combination at a range of dilutions, to allow the mycelium to grow.
  • resazurin dye is added to each well and the color in the solution is observed and compared to the color of the test solution at the same concentrations in wells without mycelial culture innoculum to control for effects of the test solution alone.
  • the resazurin dye appears blue for wells with only the initial 20 uL culture where growth has been inhibited, and appears pink for wells where mycelial growth has occurred, as shown in FIG. 2 , where the transition from blue to pink color can be clearly seen in each of the uppermost 4 rows of microtiter wells (labelled as 1-4 in FIG.
  • the Minimum Inhibitory Concentration is the lowest concentration at which growth is inhibited, and corresponds to the microtiter well in which the dye color is the same as for the control without culture and without growth, and/or in which a visual and/or optical inspection confirm that growth is inhibited.
  • Example 1 Growth Inhibition of Fusarium oxysporum by Pyraclostrobin in Combination with Several Exemplary C4-C10 Unsaturated Aliphatic Acids (or Agriculturally Acceptable Salts Thereof)
  • pyraclostrobin available from Santa Cruz Biotechnology of Dallas, Tex. as stock #229020
  • DMSO dimethylsulfoxide
  • This solution was diluted 10-fold in potato dextrose broth (PDB) to give a concentration of 0.05 mg/mL in 10% DMSO/90% PDB.
  • PDB potato dextrose broth
  • the solubility of pyraclostrobin in 10% DMSO/90% PDB was determined to be 0.0154 mg/mL using high performance liquid chromatography (HPLC).
  • a solution of (2E,4E)-2,4-hexadienoic acid, potassium salt was prepared by dissolving 2 g of (2E,4E)-2,4-hexadienoic acid, potassium salt, in 20 mL of PDB which was diluted further by serial dilution in PDB.
  • a solution of (2E,4E)-2,4-hexadienoic acid (available from Sigma-Aldrich as stock #W342904) was prepared by dissolving 20 mg of (2E,4E)-2,4-hexadienoic acid in 1 mL DMSO and adding 0.1 mL to 0.9 mL PDB resulting in a 2 mg/mL solution of (2E,4E)-2,4-hexadienoic acid in 10% DMSO/90% PDB which was diluted further by serial dilution in PDB.
  • trans-2-hexenoic acid available from Sigma-Aldrich as stock #W316903 was prepared by dissolving 100 mg trans-2-hexenoic acid in 1 mL DMSO and adding 0.1 mL to 0.9 mL PDB resulting in a 10 mg/mL solution in 10% DMSO/90% PDB which was diluted further by serial dilution in PDB.
  • a solution of trans-3-hexenoic acid (available from Sigma-Aldrich as stock #W317004) was prepared by adding 20 uL trans-3-hexenoic acid to 1980 uL PDB and the resulting solution was serially diluted in PDB. The density of trans-3-hexenoic acid was assumed to be 0.963 g/mL.
  • Combinations of pyraclostrobin and one or more exemplary C4-C10 saturated or unsaturated aliphatic acids (and agriculturally acceptable salts thereof) were prepared by adding 0.5 mL of 0.0308 mg/mL pyraclostrobin to 0.5 mL of 1.25 mg/mL (2E,4E)-2,4-hexadienoic acid, potassium salt, (combination 1), 0.5 mL of 0.25 mg/mL (2E,4E)-2,4-hexadienoic acid (combination 2), 0.5 mL of 0.625 mg/mL (2E,4E)-2,4-hexadienoic acid (combination 3), 0.5 mL of 1.25 mg/mL of trans-2-hexenoic acid (combination 4), or 0.5 mL of 0.6019 mg/mL trans-3-hexenoic acid (combination 5). Each combination was tested over a range of 2-fold dilutions in the Synergistic Growth In
  • Example 2 Growth Inhibition of Fusarium oxysporum by Fludioxonil in Combination with Several Exemplary Unsaturated Aliphatic Acids (or Agriculturally Acceptable Salts Thereof)
  • fludioxonil available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China
  • DMSO dimethylsulfoxide
  • This solution was diluted 10-fold in potato dextrose broth (PDB) to give a concentration of 0.1 mg/mL in 10% DMSO/90% PDB.
  • PDB potato dextrose broth
  • the solubility of fludioxonil in 10% DMSO/90% PDB was determined to be 0.0154 mg/mL using HPLC.
  • a solution of (2E,4E)-2,4-hexadienoic acid, potassium salt was prepared by dissolving 2 g of (2E,4E)-2,4-hexadienoic acid, potassium salt, in 20 mL of PDB which was diluted further by serial dilution in PDB.
  • a solution of (2E,4E)-2,4-hexadienoic acid (available from Sigma-Aldrich as #W342904) was prepared by dissolving 20 mg of (2E,4E)-2,4-hexadienoic acid in 1 mL DMSO and adding 0.1 mL to 0.9 mL PDB resulting in a 2 mg/mL solution of (2E,4E)-2,4-hexadienoic acid in 10% DMSO/90% PDB which was diluted further by serial dilution in PDB.
  • trans-2-hexenoic acid available from Sigma-Aldrich as stock #W316903 was prepared by dissolving 100 mg trans-2-hexenoic acid in 1 mL DMSO and adding 0.1 mL to 0.9 mL PDB resulting in a 10 mg/mL solution in 10% DMSO/90% PDB which was diluted further by serial dilution in PDB.
  • a solution of trans-3-hexenoic acid (available from Sigma-Aldrich as stock #W317004) was prepared by adding 20 uL trans-3-hexenoic acid to 1980 uL PDB and the resulting solution was serially diluted in PDB. The density of trans-3-hexenoic acid was assumed to be 0.963 g/mL.
  • Combinations of compounds A and B as shown below in Table 2 were prepared by adding 0.5 mL of 9.63 ⁇ 10 ⁇ 4 mg/mL fludioxonil to each of 0.5 mL of 0.625 mg/mL (2E,4E)-2,4-hexadienoic acid, potassium salt, (combination 1), 0.5 mL of 0.25 mg/mL (2E,4E)-2,4-hexadienoic acid (combination 2), 0.5 mL of 0.625 mg/mL of trans-2-hexenoic acid (combination 3), and 0.5 mL of 0.6019 mg/mL trans-3-hexenoic acid (combination 4). Each combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Table 2.
  • Example 3 Growth Inhibition of Fusarium oxysporum by Fludioxonil in Combination with Several Exemplary Unsaturated Aliphatic Acids
  • fludioxonil available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China
  • DMSO dimethylsulfoxide
  • This solution was diluted 10-fold in potato dextrose broth (PDB) to give a concentration of 0.1 mg/mL in 10% DMSO/90% PDB.
  • PDB potato dextrose broth
  • the solubility of fludioxonil in 10% DMSO/90% PDB was determined to be 0.0154 mg/mL using HPLC.
  • Stock solutions of several exemplary C4-C10 unsaturated aliphatic acids as Compound B for testing individual MICs were prepared at 25 uL/mL in DMSO by adding 25 uL of each Compound B to 975 uL DMSO, followed by 10-fold dilution in PDB, for each of 3-octenoic acid (available from Sigma-Aldrich as stock #CDS000466), trans-2-octenoic acid (available from Sigma-Aldrich), 9-decenoic acid (available from Sigma-Aldrich as #W366005), 3-decenoic acid (available from Sigma-Aldrich as stock #CDS000299), and trans-2-decenoic acid (available from TCI America as stock #D0098).
  • 3-octenoic acid available from Sigma-Aldrich as stock #CDS000466
  • trans-2-octenoic acid available from Sigma-Aldrich
  • 9-decenoic acid available from Sigma-Aldrich as
  • solutions of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid were prepared at 0.78 uL/mL in DMSO by adding 3.125 uL of each Compound B to 2 mL of DMSO, followed by 2-fold dilution in DMSO to give 0.78 uL/mL.
  • Solutions of 3-decenoic acid and trans-2-decenoic acid were prepared similarly, but applying a further 2-fold dilution in DMSO to give a concentration of 0.39 uL/mL in DMSO.
  • Combinations of the exemplary Compound B components with fludioxonil were prepared by adding 0.5 mL of 0.078 uL/mL of each of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid or 0.039 uL/mL of each of 3-decenoic acid and trans-2-decenoic acid, to 0.5 mL of 4.813 ⁇ 10 ⁇ 4 mg/mL fludioxonil obtained from serial dilution of 0.0154 mg/mL of fludioxonil in 10% DMSO/90% PDB, as prepared above, with PDB.
  • the density of 3-octenoic acid was assumed to be 0.938 g/mL.
  • trans-2-octenoic acid was assumed to be 0.955 g/mL.
  • the density of 3-decenoic acid was assumed to be 0.939 g/mL.
  • the density of trans-2-decenoic acid was assumed to be 0.928 g/mL.
  • the density of 9-decenoic acid was assumed to be 0.918 g/mL.
  • Example 4 Growth Inhibition of Fusarium oxysporum by Thyme Oil in Combination in Combination with Several Exemplary Unsaturated Aliphatic Acids
  • thyme oil available from Sigma-Aldrich as stock #W306509
  • DMSO dimethylsulfoxide
  • Stock solutions of several exemplary C4-C10 unsaturated aliphatic acids as Compound B for testing individual MICs were prepared at 25 ⁇ L/mL by adding 25 ⁇ L of each of 3-octenoic acid (available from Sigma-Aldrich as stock #CDS000466), trans-2-octenoic acid (available from Sigma-Aldrich as stock #CDS000466), 9-decenoic acid (available from Sigma-Aldrich as stock #W366005), 3-decenoic acid (available from Sigma-Aldrich as stock #CDS000299), and trans-2-decenoic acid (available from TCI America as stock #D0098), to 975 ⁇ L DMSO followed by 10-fold dilution in PDB.
  • Stock solutions of the exemplary C4-C10 unsaturated aliphatic acids as Compound B for testing in combination with thyme oil were prepared by adding 3.125 ⁇ L of each of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid, to 2 mL of DMSO followed by 2-fold dilution in DMSO to give a 0.78 L/mL concentration stock solution. Solutions of 3-decenoic acid and trans-2-decenoic acid were prepared similarly, but applying a further 2-fold dilution in DMSO to give a concentration of 0.39 ⁇ L/mL.
  • Combinations of the exemplary Compound B components with thyme oil were prepared by adding 0.5 mL of 0.078 i/mL of each of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid or 0.039 ⁇ L/mL of each of 3-decenoic acid and trans-2-decenoic acid, to 0.5 mL of 1.25 mg/mL thyme oil in 10% DMSO/90% PDB.
  • the density of 3-octenoic acid was assumed to be 0.938 g/mL.
  • the density of trans-2-octenoic acid was assumed to be 0.955 g/mL.
  • the density of 3-decenoic acid was assumed to be 0.939 g/mL.
  • the density of trans-2-decenoic acid was assumed to be 0.928 g/mL.
  • the density of 9-decenoic acid was assumed to be 0.918 g/mL
  • Example 5 Growth Inhibition of Botrytis cinerea by Neem Oil Limonoid Extract (Extracted from Cold-Pressed Neem Oil) and Fortune Aza Technical (Azadirachtin Extract) in Combination with Various Exemplary Unsaturated Aliphatic Acids
  • An extract of limonoids was prepared from cold-pressed neem oil using solvent extraction with hexane and methanol to prepare a neem oil limonoid extract.
  • Fortune Aza Technical pesticide containing 14% azadirachtin was obtained from Fortune Biotech Ltd. of Secunderabad, India.
  • Solutions of neem oil limonoid extract and Fortune Aza Technical were prepared at 5 mg/mL in DMSO followed by ten-fold dilution in PDB to give a concentration of 0.5 mg/mL in 10% DMSO/90% PDB.
  • Combinations were prepared by adding 0.5 mL of 6.25 ⁇ L/mL, 3.125 ⁇ L/mL, or 0.625 ⁇ L/mL 3-octenoic acid ortrans-2-octenoic acid, as prepared above (as Compound B), to 0.5 mL neem oil limonoid extract or Fortune Aza Technical at 0.5 mg/mL in acid DMSO/90% PDB (as Compound A) for testing in the synergistic growth inhibition assay. Each combination was observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Tables 5 and 6.
  • Example 6 Growth Inhibition of Fusarium oxysporum by Fludioxonil in Combination with Various Exemplary Saturated Aliphatic Acids
  • fludioxonil 20 mg fludioxonil was dissolved in 10 mL dimethylsulfoxide (DMSO) and the resulting solution was diluted 2-fold in DMSO to give a concentration of 1 mg/mL. This solution was diluted 10-fold in potato dextrose broth (PDB) to give a concentration of 0.1 mg/mL in 10% DMSO/90% PDB. The solubility of fludioxonil in 10% DMSO/90% PDB was determined to be 0.0154 mg/mL using high performance liquid chromatography. A solution of 0.000963 mg/mL fludioxonil was prepared by adding 625 ⁇ L of 0.0154 mg/mL fludioxonil to 9375 ⁇ L of PDB.
  • DMSO dimethylsulfoxide
  • PDB potato dextrose broth
  • stock solutions of hexanoic acid or octanoic acid as Component B were prepared by adding 100 ⁇ L hexanoic acid (93 mg) or octanoic acid (91 mg) to 900 ⁇ L PDB resulting in concentrations of 9.3 mg/mL and 9.1 mg/mL, respectively.
  • a stock solution of decanoic acid was prepared at 10 mg/mL in DMSO followed by 10-fold dilution in PDB producing a concentration of 1 mg/mL in 10% DMSO/90% PDB.
  • the stock solution of decanoic acid, potassium salt was prepared by adding 100 mg to 10 mL of PDB resulting in a concentration of 10 mg/mL.
  • a stock solution of dodecanoic acid was prepared at 1 mg/mL in DMSO followed by 10-fold dilution in PDB producing a concentration of 0.1 mg/mL in 10% DMSO/90% PDB.
  • a solution of hexanoic acid at 0.29 mg/mL was prepared by adding 156 ⁇ L of the 9.3 mg/mL stock solution to 4844 ⁇ L PDB.
  • a solution of octanoic acid at 1.14 mg/mL was prepared diluting the 9.1 mg/mL stock solution in PDB.
  • a solution of decanoic acid at 0.5 mg/mL was prepared by 2-fold dilution of the 1 mg/mL stock solution.
  • a solution of decanoic acid, potassium salt, at 0.156 mg/mL was prepared by adding 78 ⁇ L of the 10 mg/mL stock solution to 4922 ⁇ L PDB.
  • a solution of dodecanoic acid at 0.2 mg/mL was prepared by dissolving 2 mg in 1 mL DMSO followed by 10-fold dilution in PDB at 40° C.
  • Combinations for results shown in Table 7 were prepared by adding 0.5 mL of 0.0154 mg/mL fludioxonil to 0.5 mL of each of the stock solutions. Each combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Table 7.
  • Combinations for results shown in Table 8 were prepared by adding 0.5 mL of 0.000963 mg/mL fludioxonil to 0.5 mL of each of the stock solutions.
  • Example 7 Growth Inhibition of Fusarium oxysporum by Limonoid Extract from Cold-Pressed Neem Oil and Fortune Aza Technical (Azadirachtin Extract) in Combination with Various Exemplary Saturated Aliphatic Acids
  • An extract of limonoids was prepared from cold-pressed neem oil using solvent extraction with hexane and methanol to prepare a neem oil limonoid extract.
  • Fortune Aza Technical pesticide containing 14% azadirachtin was obtained from Fortune Biotech Ltd. of Secunderabad, India (also referred to as “Azatech”).
  • Solutions of neem oil limonoid extract and Fortune Aza Technical were prepared at 5 mg/mL in DMSO followed by ten-fold dilution in PDB to give a concentration of 0.5 mg/mL in 10% DMSO/90% PDB. These solutions were used for testing the individual MICs.
  • a solution was prepared by adding 100 uL octanoic acid (91 mg) to 900 uL PDB resulting in concentrations of 9.1 mg/mL.
  • a stock solution of decanoic acid was prepared at 10 mg/mL in DMSO followed by 10-fold dilution in PDB producing a concentration of 1 mg/mL in 10% DMSO/90% PDB.
  • Combinations with decanoic acid were prepared by dissolving 5 mg neem oil limonoid extract or Fortune Aza Technical in 1 mL of DMSO and adding 2.5 mg of decanoic acid followed by 10-fold dilution in PDB. This produced a solution containing 0.5 mg/mL neem oil limonoid extract or Fortune Aza Technical and 0.25 mg/mL decanoic acid.
  • Concentrated stock solutions were prepared by dissolving pesticidal active ingredient in 100% dimethylsulfoxide (DMSO), which were then diluted 10-fold in potato dextrose broth (PDB) to give a working stock solution, as described below:
  • DMSO dimethylsulfoxide
  • PDB potato dextrose broth
  • Pyraclostrobin available from Santa Cruz Biotech, Dallas, Tex., USA, as stock 4 SC-229020: A 0.5 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.05 mg/mL working stock solution, for which an effective solubilized concentration of 0.015 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.015 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • HPLC high performance liquid chromatography
  • Azoxystrobin available from Sigma-Aldrich, St. Louis, Mo., USA, as stock #31697: A 1.75 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.175 mg/mL working stock solution, for which an effective solubilized concentration of 0.15 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.15 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • HPLC high performance liquid chromatography
  • Chlorothalonil available from Chem Service Inc., West Chester, Pa., USA, as stock #N-11454.
  • a 0.5 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.05 mg/mL working stock solution, for which an effective solubilized concentration of 0.002 mg/mL was verified using high performance liquid chromatography (HPLC).
  • HPLC high performance liquid chromatography
  • Fludioxonil available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China: A 1.05 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.105 mg/mL working stock solution, for which an effective solubilized concentration of 0.021 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.021 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • HPLC high performance liquid chromatography
  • Cyprodinil (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China): A 1.37 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.137 mg/mL working stock solution, for which an effective solubilized concentration of 0.009 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.009 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Metalaxyl A 3.32 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.332 mg/mL working stock solution, for which an effective solubilized concentration of 0.316 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.316 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Difenoconazole (available from Santa Cruz Biotech, Dallas, Tex., USA, as stock no. SC-204721): A 1.3 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.13 mg/mL working stock solution, for which an effective solubilized concentration of 0.051 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.051 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • HPLC high performance liquid chromatography
  • Propiconazole (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China): A 1.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.10 mg/mL working stock solution, for which an effective solubilized concentration of 0.089 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.089 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • HPLC high performance liquid chromatography
  • Epoxiconazole (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China): A 2.5 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.25 mg/mL working stock solution, for which an effective solubilized concentration of 0.03 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.025 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Tebuconazole (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working stock solution, for which an effective solubilized concentration of 0.45 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.45 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in Tables the tables below.
  • Picoxystrobin available from Sigma Aldrich, #33658: A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working picoxystrobin stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Isopyrazam available from Sigma Aldrich, #32532: A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working isopyrazam stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Penthiopyrad (available from aksci.com, #X5975): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working penthiopyrad stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Oxathiapiprolin (available from carbosynth.com, #FO159014): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working oxathiapiprolin stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Prothioconazole available from Sigma Aldrich, #34232: A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working prothioconazole stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Trifloxystrobin (available from Sigma Aldrich, #46447): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working trifloxystrobin stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Mancozeb available from Sigma Aldrich, #45553: A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working penthiopyrad stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Thyme oil available from Sigma-Aldrich, St. Louis, Mo., USA as stock #W306509), garlic oil (available from New Directions Aromatics, Missisauga, ON, Canada), lemongrass oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OL123), wintergreen oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OW134), peppermint oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OP1531), spearmint oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #AS132), clove leaf oil (available from New Directions Aromatics, Missisauga, ON, Canada), cinnamon leaf oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OC2131), tea tree oil (available from Newco Natural Technology, Calgary, AB, Canada), geranium oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OW
  • This 10 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Nootkatone(+) available from Alfa Aesar, Ward Hill, Mass., USA as stock #A19166: A 10 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 1.0 mg/mL concentration. This 1.0 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in Tables 10-111 below.
  • Neem oil limonoid extract An extract of limonoids was prepared from cold-pressed neem oil using solvent extraction with hexane and methanol to prepare a neem oil limonoid extract. A 5 mg/mL stock solution of neem oil limonoid extract in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 0.5 mg/mL concentration. This 0.5 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Karanja oil flavonoid extract An extract of flavonoids was prepared from cold-pressed karanja oil by solvent extraction. A 5 mg/mL stock solution of karanja oil flavonoid extract in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 0.5 mg/mL concentration. This 0.5 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Salannin was extracted and purified from cold-pressed neem oil by solvent extraction. A 1 mg/mL stock solution of salannin in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 0.1 mg/mL concentration. This 0.1 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Concentrated stock solutions were prepared by dissolving each exemplary unsaturated aliphatic acid in 100% dimethylsulfoxide (DMSO), which were then diluted 10-fold in potato dextrose broth (PDB) to give a working stock solution, as described below:
  • DMSO dimethylsulfoxide
  • PDB potato dextrose broth
  • trans-2-decenoic acid available from TCI America, Portland, Oreg., USA as stock #D0098
  • cis-2-decenoic acid available from BOC Sciences, Sirley, N.Y., USA
  • trans-2-undecenoic acid available from Alfa Aesar, Ward Hill, Mass., USA as stock #L-11579
  • a 50 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 5 mg/mL concentration. This 5 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • (2E,4E)-2,4-hexadienoic acid available from Sigma-Aldrich, St. Louis, Mo., USA: A 20 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 2 mg/mL concentration. This 2 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Concentrated stock solutions were prepared by dissolving each exemplary saturated aliphatic acid in 100% dimethylsulfoxide (DMSO), which were then diluted 10-fold in potato dextrose broth (PDB) to give a working stock solution, as described below:
  • DMSO dimethylsulfoxide
  • PDB potato dextrose broth
  • Hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid (all available from Sigma-Aldrich, St. Louis, Mo., USA): A 50 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 5 mg/mL concentration. This 5 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in data Tables below.
  • Decenoic acid available from Sigma-Aldrich, St. Louis, Mo., USA: A 10 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 1 mg/mL concentration. This 1 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in data Tables below.
  • Dodecenoic acid available from Sigma-Aldrich, St. Louis, Mo., USA: A 1 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 0.1 mg/mL concentration. This 0.1 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in data Tables below.
  • Exemplary Hydroxy-substituted aliphatic acids 2- and 3-hydroxybutyric acid, 2-hydroxyhexanoic acid, 12-hydroxydodecanoic acid (all available from Sigma-Aldrich, St. Louis, Mo., USA); 3-hydroxydecanoic acid, 3-hydroxyhexanoic acid (both available from Shanghai Terppon Chemical, Shanghai, China); 3-, 8-, 10-hydroxyoctanoic acid (all available from AA Blocks LLC, San Diego, Calif., USA), 2-hydroxyoctanoic acid (available from Alfa Aesar, Ward Hill, Mass., USA): a stock solution was prepared for each by dissolving each acid in 100% DMSO, which was then diluted in PDB to 10% DMSO concentration, before further serial dilution in PDB to the required individual concentrations as specified in the data Tables below.
  • alkyl-substituted aliphatic acids 2-ethylhexanoic acid, 2-methyloctanoic acid, 3-methylnonanoic acid, 3-methylbutyric acid (all available from Sigma-Aldrich, St.
  • Exemplary amino-substituted aliphatic acid 3-aminobutyric acid (available from AK Scientific Inc., Union City, Calif., USA): a stock solution was prepared by dissolving each acid in 100% DMSO, which was then diluted in PDB to 10% DMSO concentration, before further serial dilution in PDB to the required individual concentrations as specified in the data Tables below.
  • each Compound A and Compound B component were then serially diluted to test the individual MIC of each pesticidal active ingredient (as Compound A), each unsaturated or saturated aliphatic acid (as Compound B), and the combined MIC of each combination of Compound A and Compound B, according to the synergistic growth inhibition assay described above.
  • Example 8 Growth Inhibition of Fusarium oxysporum by Pyraclostrobin, Azoxystrobin, Chlorothalonil, Fluidioxonil, Cyprodinil, Difenoconazole, and Tebuconazole, in Combination with Various Exemplary Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, chlorothalonil, fluidioxonil, cyprodinil, difenoconazole, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 10-15 below.
  • Working solutions of hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, and decanoic acid, (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 10-15 below.
  • Example 9 Growth Inhibition of Sclerotinta Sclerotiorum by Pyraclostrobin, Azoxystrobin, Propiconazole, Epiconazole, Tebuconazole, and Difenoconazole, in Combination with Various Exemplary Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, propiconazole, epiconazole, tebuconazole, and difenoconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 16-20 below.
  • Working solutions of hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, and dodecanoic acid, (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 16-20 below.
  • Example 10 Growth Inhibition of Botrytis cinerea by Pyraclostrobin, Azoxystrobin, Cyprodinil, Metalaxyl, Epiconazole, Tebuconazole, Propiconazole, and Difenoconazole, in Combination with Various Exemplary Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, cyprodiil, metalaxyl, epiconazole, tebuconazole, propiconazole, and difenoconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 21-26 below.
  • Working solutions of hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, and dodecanoic acid, (as Compound B) were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 21-26 below. Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 48 hours, and the FIC Index for each combination calculated, as shown in Tables 21-26 below
  • Example 11 Growth Inhibition of Fusarium oxysporum by Pyraclostrobin, Azoxystrobin, Fludioxonil, Cyprodinil, Difenoconazole, Epoxiconazole, and Tebuconazole, in Combination with Various Exemplary Unsaturated Aliphatic Acids
  • Example 12 Growth Inhibition of Sclerotinia sclerotiorum by Pyraclostrobin, Azoxystrobin, Chlorothalonil, Fludioxonil, Difenoconazole, Propiconazole, Epoxiconazole, and Tebuconazole, in Combination with Various Exemplary Unsaturated Aliphatic Acids
  • Example 13 Growth Inhibition of Botrytis cinerea by Pyraclostrobin, Azoxystrobin, Chlorothalonil, Cyprodinil, Metalaxyl, Epoxiconazole, and Tebuconazole, in Combination with Various Exemplary Unsaturated Aliphatic Acids
  • Example 15 Growth Inhibition of Botrytis cinerea by Pyraclostrobin, Azoxystrobin, Cyprodinil, Difenoconazole, Epoxiconazole and Tebuconazole, in Combination with Various Exemplary Hydroxy-Substituted Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, cyprodinil, difenoconazole, epoxiconazole and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Table 51 below.
  • Example 16 Growth Inhibition of Fusarium oxysporum by Pyraclostrobin, Azoxystrobin, Fludioxonil, and Tebuconazole, in Combination with Various Exemplary Hydroxy-Substituted Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, fludioxonil, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 52-54 below.
  • Working solutions of 2-hydroxybutyric acid, 2-hydroxyhexanoic acid, 2-hydroxyoctanoic acid, 3-hydroxyoctanoic acid, 8-hydroxyoctanoic acid, and 10-hydroxydecanoic acid, (as Compound B) were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 52-54 below.
  • Example 17 Growth Inhibition of Sclerotinia sclerotiorum by Pyraclostrobin, Azoxystrobin, Fludioxonil, Difenoconazole, and Tebuconazole, in Combination with Various Exemplary Hydroxy-Substituted Aliphatic Acids
  • Example 18 Growth Inhibition of Botryrtis cinerea by Various Exemplary Synthetic Fungicides, in Combination with Various Exemplary Hydroxy-Substituted Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, fludioxonil, tebuconazole, and difenoconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 58-61 below.
  • Working solutions of 2-hydroxybutyric, 2-hydroxyhexanoic, 2-hydroxyoctanoic, 10-hydroxydecanoic, 12-hydroxydodecanoic, 3-hydroxyoctanoic, 8-hydroxyoctanoic acids, were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 58-61 below.
  • Example 19 Growth Inhibition of Sclerotinta Sclerotiorum by Pyraclostrobin, Azoxystrobin, Fludioxonil, and Tebuconazole, in Combination with Various Exemplary Alkyl-Substituted Aliphatic Acids
  • Working solutions ofpyraclostrobin, azoxystrobin, fludioxonil, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 62-66 below.
  • Working solutions of2,2-diethylbutanoic acid, 3-methylbutyric acid, 2-ethylhexanoic acid, 3-methylhexanoic acid, 4-methylhexanoc acid, and 2-methyloctanoic acid, (as Compound B) were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 62-66 below.
  • Example 20 Growth Inhibition of Botrytis cinerea by Pyraclostrobin, Azoxystrobin, Difenoconazole, and Tebuconazole, in Combination with Various Exemplary Alkyl-Substituted Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, difenoconazole, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 67-70 below.
  • Working solutions of 2,2-diethylbutanoic acid, 3-methylbutyric acid, 2-ethylhexanoic acid, 3-methylhexanoic acid, 4-methylhexanoic acid, and 2-methyloctanoic acid, and 2-methyldecanoic acid (as Compound B) were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 67-70 below.
  • Example 21 Growth Inhibition of Botrytis cinerea by Picoxystrobin, Mancozeb, Isopyrazam, Oxathiapiprolin, Penthiopyrad, Prothioconazole and Trifloxystrobin, in Combination with Various Exemplary C4-C10 Saturated, Unsaturated, Hydroxy-, Methyl-, Ethyl-, and Diethyl-Substituted Aliphatic Acids
  • MIC A
  • B Ratio Compound FIC Combination Compound A
  • Compound B mg/mL
  • Picoxystrobin Decanoic acid 0.03125 0.0078125 0.25 0.63
  • Picoxystrobin Trans-2-hexenoic 0.0625 0.019531 0.3 0.38 acid
  • MIC A
  • B Ratio Compound FIC Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index Mancozeb 0.03125 Trans-2-octenoic acid 0.039062 3-Decenoic acid 0.039062 1 Mancozeb Trans-2-octenoic acid 0.003906 0.019531 5 0.63 2 Mancozeb 3-Decenoic acid 0.003906 0.019531 5 0.63
  • Example 22 Growth Inhibition of Alternaria Solani by Picoxystrobin, Mancozeb, Penthiopyrad, and Prothioconazole, in Combination with Various Exemplary C4-C10 Saturated, Unsaturated, Hydroxy-, Methyl-, Ethyl-, and Diethyl-Substituted Aliphatic Acids
  • Example 23 Growth Inhibition of Sclerotinia sclerotiorum by Picoxystrobin, Penthiopyrad, and Prothioconazole, in Combination with Various Exemplary C4-C10 Saturated, Unsaturated, Hydroxy-, Methyl-, and Ethyl-Substituted Aliphatic Acids
  • synergistic efficacy is shown for many exemplary synergistic pesticidal compositions according to some embodiments of the present disclosure, such synergistic pesticidal compositions comprising at least a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12) saturated or unsaturated aliphatic acid or salt thereof.
  • a synergistic composition predictive model was constructed using neural network machine learning computational techniques, to provide a synergistic compound screening system that is trained using experimentally determined in vitro results showing synergistic and non-synergistic pesticidal efficacy of pesticidal compositions comprising a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12) saturated or unsaturated aliphatic acid or salt thereof, and which determines a probability of synergistic efficacy of a specific such pesticidal composition.
  • a synergistic composition predictive system was constructed using an ensemble of machine learning models, and which provides a predicted probability that a candidate pesticidal composition comprising a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12) saturated or unsaturated aliphatic acid or salt thereof will exhibit synergistic pesticidal efficacy in vitro against a target pathogen or pest.
  • Each individual predictive model within the ensemble was initialized differently and each such model was trained using a selected portion of an in vitro synergistic pesticidal composition training dataset, leaving a remaining portion of the dataset for validation of each individual predictive model.
  • This approach allows for a diversity between the individual predictive models in the ensemble, resulting in improved average predictive accuracy of the combined predictions of synergy across the ensemble of models, for a particular candidate pesticidal composition
  • a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12) saturated or unsaturated aliphatic acid or salt.
  • a separate synergistic composition predictive model was constructed for predicting probability of synergy of a candidate pesticidal composition for each of three exemplary target pathogens or pests, including Fusarium oxysporum, Botrytis cinerea , and Sclerotinia sclerotiorum , and each such model was trained using an experimentally obtained dataset of in vitro synergistic efficacy results for a multiplicity of in vitro screened pesticidal compositions comprising a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12). Each such model was validated using non-training portions of the in vitro experimental synergistic pesticidal composition dataset for the relevant pathogen, to determine and optimize its predictive performance in predicting in vitro synergy.
  • Fusarium oxysporum was used as a representative pest organism or pathogen to determine a predicted probability of synergy for pesticidal compositions comprising a pesticidal active ingredient agent (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent or salt thereof (compound B).
  • Botrytis cinerea was used as a representative pest organism or pathogen to determine a predicted probability of synergy for pesticidal compositions comprising a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent or salt thereof (compound B).
  • Sclerotinia sclerotiorum was used as a representative pest organism or pathogen to determine a predicted probability of synergy for pesticidal compositions comprising a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent or salt thereof (compound B).
  • an exemplary threshold of predicted probability of synergy greater than 55% (or 0.55) was applied to determine exemplary predictions of in vitro synergistic interaction between a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent or salt thereof (compound B) in a synergistic pesticidal composition.
  • Results of exemplary predictions of in vitro synergistic pesticidal efficacy against an exemplary pathogen or pest made using a synergistic composition predictive system as described above are shown in the following Tables 89-91.
  • Example 24 Predicted synergistic efficacy for in vitro growth inhibition of Fusarium oxysporum by benzovindiflupyr, bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, oxathiapiprolin, penflufen, penthiopyrad, picoxystrobin, prothioconazole, pydiflumetofen, revysol, sedaxane, trifloxystrobin, and valifenalate, in combination with various exemplary saturated and unsaturated C4-C12 aliphatic acids, according to an embodiment of the present disclosure.
  • Example 25 Predicted synergistic efficacy for in vitro growth inhibition of Sclerotinia sclerotiorum by bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, penflufen, penthiopyrad, picoxystrobin, pydiflumetofen, revysol, trifloxystrobin, and valifenalate, in combination with various exemplary saturated and unsaturated C4-C12 aliphatic acids, according to an embodiment of the present disclosure.
  • Example 26 Predicted synergistic efficacy for in vitro growth inhibition of Botritis cinerea by bixafen, fenpicoxamid, florylpicoxamid, fluxapyroxad, kresoxim-methyl, picoxystrobin, pydiflumetofen, revysol, trifloxystrobin, and valifenalate, in combination with various exemplary saturated and unsaturated C4-C12 aliphatic acids, according to an embodiment of the present disclosure.
  • the combination of a C4-C10 unsaturated aliphatic acid (and agriculturally acceptable salts thereof in some particular embodiments) and a pesticidal active ingredient produces a synergistic pesticidal composition demonstrating or reasonably predicted to demonstrate a synergistic effect. That is, when used in combination, the C4-C10 unsaturated aliphatic acid and the pesticidal active ingredient have or are reasonably predicted to have an efficacy that is greater than would be expected by simply adding the efficacy of the pesticidal active ingredient and the C4-C10 unsaturated aliphatic acid when used alone.
  • the unsaturated aliphatic acid or agriculturally acceptable salt thereof may comprise a C11 unsaturated aliphatic acid or agriculturally acceptable salt thereof. In some further alternative embodiments, the unsaturated aliphatic acid or agriculturally acceptable salt thereof may comprise a C12 unsaturated aliphatic acid or agriculturally acceptable salt thereof.
  • the combination of a C4-C10 saturated aliphatic acid (and agriculturally acceptable salts thereof in some particular embodiments) and a pesticidal active ingredient produces a synergistic pesticidal composition demonstrating a synergistic effect or reasonably predicted to demonstrate a synergistic effect. That is, when used in combination, the C4-C10 saturated aliphatic acid and the pesticidal active ingredient have or are predicted to have an efficacy that is greater than would be expected by simply adding the efficacy of the pesticidal active ingredient and the C4-C10 saturated aliphatic acid when used alone.
  • the combination of a C4-C10 saturated aliphatic acid and a neem seed, kernel, oil, extract or derivative pesticidal active ingredient produces a synergistic pesticidal composition demonstrating a synergistic pesticidal effect.
  • the combination of a C11 or C12 saturated aliphatic acid and a neem seed, kernel, oil, extract or derivative pesticidal active ingredient produces a synergistic pesticidal composition demonstrating or reasonably predicted to demonstrate a synergistic pesticidal effect.
  • the combination of a C11 or C12 saturated aliphatic acid (and agriculturally acceptable salts thereof in some particular embodiments) and a pesticidal active ingredient produces a synergistic pesticidal composition demonstrating a synergistic effect.

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Abstract

Compositions and methods for increasing the efficacy of pesticidal compositions are described herein, including synergistic pesticidal compositions comprising: benzovindiflupyr, bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, oxathiapiprolin, penflufen, penthiopyrad, picoxystrobin, prothioconazole, pydiflumetofen, revysol, sedaxane, trifloxystrobin, pyraclostrobin, azoxystrobin, chlorothalonil, cyprodinil, metalaxyl, epoxiconazole, propiconazole, difenoconazole, fludioxonil, mancozeb, tebuconazole, valifenalate, in combination with a C4-C10 saturated or unsaturated aliphatic acid and methods for delivery of pesticidal active ingredients. Some pesticidal compositions and methods as described are directed to compositions and methods for increasing the efficacy of fungicides. Some pesticidal compositions and methods as described are directed to compositions and methods for increasing the efficacy of nematicides. Some pesticidal compositions and methods as described are directed to compositions and methods for increasing the efficacy of insecticides. Methods for enhancing the activity pesticidal active ingredients in pesticidal compositions in use are also described.

Description

    REFERENCE TO RELATED APPLICATIONS
  • This application claims priority to, and the benefit of, US provisional patent application Nos. 62/737,907 filed 27 Sep. 2018; 62/737,914 filed 27 Sep. 2018; 62/829,512 filed 4 Apr. 2019; and 62/829,525 filed 4 Apr. 2019, all entitled SYNERGISTIC PESTICIDAL COMPOSITIONS AND METHODS FOR DELIVERY OF ACTIVE INGREDIENTS, all of which are incorporated by reference herein in their entireties.
    • TECHNICAL FIELD
  • An embodiment of the present invention is related to compositions and methods for increasing the efficacy of pesticidal compositions. More particularly, some embodiments are related to synergistic pesticidal compositions and methods for delivery of pesticidal active ingredients. Some embodiments of the present invention are directed to compositions and methods for increasing the efficacy of fungicides.
  • Some embodiments of the present invention are directed to compositions and methods for increasing the efficacy of nematicides. Some embodiments of the present invention are directed to compositions and methods for increasing the efficacy of insecticides. Further embodiments of the present invention are directed to methods for enhancing the activity pesticidal active ingredients in pesticidal compositions.
    • BACKGROUND
  • Pesticides, including fungicides, herbicides, nematicides and insecticides, are important compositions for use in domestic, agricultural, industrial and commercial settings, such as to provide for control of unwanted pests and/or pathogens. Providing for effective pest control is of high importance in many such settings, since pests and/or other pathogens if not controlled can cause loss and or destruction of crops or other plants, or harm to animals, humans or other beneficial or desired organisms. There remains a need for environmentally safe and effective pesticides, including fungicides, nematicides and insecticides, or compounds that enhance the efficacy of pesticides, including fungicides, nematicides and insecticides, and for methods of enhancing the efficacy of pesticides including fungicides, nematicides and insecticides, so that pesticides can be used in a more environmentally safe and effective manner. In agricultural settings, for example, a variety of plant pests, such as insects, worms, nematodes, fungi, and plant pathogens such as viruses and bacteria, are known to cause significant damage to seeds and ornamental and crop plants. Chemical pesticides have generally been used, but many of these are expensive and potentially toxic to humans, animals, and/or the environment and may persist long after they are applied. Therefore it is typically beneficial to farmers, consumers and the surrounding environment to use the least amount of chemical pesticides as possible, while continuing to control pest growth in order to maximize crop yield. In a growing number of cases, chemical pesticide use has also resulted in growing resistance to certain chemical pesticides by pest organisms, leading to reduced effectiveness, requiring greater doses of pesticidal chemicals, or even failure of certain types of pesticides as viable control agents. As a result, many chemical pesticides are being phased out or otherwise restricted from use.
  • Natural or biologically-derived pesticidal compounds have been proposed for use in place of some chemical pesticides, in order to attempt to reduce the toxicity, health and environmental risks associated with chemical pesticide use. However, some natural or biologically-derived pesticides have proven less efficacious or consistent in their performance in comparison with competing chemical pesticides, which has limited their adoption as control agents in pesticide markets.
  • Therefore, there remains a need to provide improved pesticides and pesticidal compositions to allow for effective, economical and environmentally and ecologically safe control of insect, plant, fungal, nematode, mollusk, mite, viral and bacterial pests. In particular, there remains a need to provide for pesticidal compositions that desirably minimize the amount of pesticidal agents or pesticidal active ingredients required to obtain desired or acceptable levels of control of pests in use.
  • Accordingly, there remains a need to provide synergistic pesticidal compositions that desirably minimize the use of pesticidal agents or pesticidal active ingredients through synergistic efficacy, to provide for desired pest control performance in use. However, large-scale experimental drug combination studies in non-agricultural fields have found that synergistic combinations of drug pairs are extremely complex and rare, with only a 4-10% probability of finding synergistic drug pairs [Yin et al., PLOS 9:e93960 (2014); Cokol et al., Mol. Systems Biol. 7:544 (2011)]. In fact, a systematic screening of about 120,000 two-component drug combinations based on reference-listed drugs found fewer than 10% synergistic pairs, as well as only 5% synergistic two-component pairs for fluconazole, a triazole fungicidal compound related to certain azole agricultural fungicide compounds [Borisy et al., Proc. Natl Acad. Sci. 100:7977-7982 (2003)].
  • The foregoing examples of the related art and limitations related thereto are intended to be illustrative and not exclusive. Other limitations of the related art will become apparent to those of skill in the art upon consideration of the present disclosure.
    • BRIEF SUMMARY
  • In one embodiment according to the present disclosure, a synergistic pesticidal composition is provided, comprising a pesticidal active ingredient; and a C4-C10 unsaturated aliphatic acid (including an unsaturated C6, C7, C8, C9 or C10 aliphatic acid) or an agriculturally compatible salt thereof, wherein the C4-C10 unsaturated aliphatic acid comprises at least one unsaturated C—C bond and wherein a ratio of the concentrations by weight of said pesticidal active ingredient and said C4-C10 unsaturated aliphatic acid or an agriculturally compatible salt thereof is between about 1:15,000 and 15,000:1, and more particularly between about 1:5000 and 5000:1, and further more particularly between about 1:2000 and 2000:1. In another embodiment, a synergistic pesticidal composition is provided, comprising a pesticidal active ingredient; and a C4-C10 saturated aliphatic acid (including a saturated C4, C5, C6, C7, C8, C9 or C10 aliphatic acid) or an agriculturally compatible salt thereof, wherein a ratio of the concentrations by weight of said pesticidal active ingredient and said C4-C10 saturated aliphatic acid or an agriculturally compatible salt thereof is between about 1:15,000 and 15,000:1, and more particularly between about 1:5000 and 5000:1, and further particularly between about 1:2000 and 2000:1. In yet another embodiment, a synergistic pesticidal composition is provided, comprising a pesticidal active ingredient; and a C11 unsaturated or saturated aliphatic acid or an agriculturally compatible salt thereof, wherein a ratio of the concentrations by weight of said pesticidal active ingredient and said C11 unsaturated or saturated aliphatic acid or an agriculturally compatible salt thereof is between about 1:15,000 and 15,000:1, and more particularly between about 1:2000 and 2000:1. In yet a further embodiment, a synergistic pesticidal composition is provided, comprising a pesticidal active ingredient; and a C12 unsaturated or saturated aliphatic acid or an agriculturally compatible salt thereof, wherein a ratio of the concentrations by weight of said pesticidal active ingredient and said C12 unsaturated or saturated aliphatic acid or an agriculturally compatible salt thereof is between about 1:15,000 and 15,000:1, more particularly between about 1:5000 and 5000:1, and further particularly between about 1:2000 and 2000:1. In a further embodiment, a method of synergistically enhancing the pesticidal activity of at least one pesticidal active ingredient adapted to control at least one target pest organism is provided, comprising: providing at least one pesticidal active ingredient active for said at least one target pest organism; adding a synergistically effective concentration of at least one C4-C10 unsaturated aliphatic acid comprising at least one unsaturated C—C bond, or an agriculturally acceptable salt thereof, to said pesticidal active ingredient to provide a synergistic pesticidal composition; and applying said synergistic pesticidal composition in a pesticidally effective concentration to control said at least one target pest organism. In another embodiment, instead of a C4-C10 unsaturated aliphatic acid, a C4-C10 saturated aliphatic acid or agriculturally compatible salts thereof may be provided to provide the synergistic pesticidal composition. In yet another embodiment, a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof may be provided to provide the synergistic pesticidal composition. In yet a further embodiment, a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof may be provided to provide the synergistic pesticidal composition. In some embodiments, the synergistic pesticidal composition may comprise a C4-C10 unsaturated or saturated aliphatic acid or a biologically compatible salt thereof, wherein said salt comprises at least one of an agriculturally, aquatic life, or mammal-compatible salt, for example. In other embodiments, a C11 unsaturated or saturated aliphatic acid or biologically compatible salt thereof, or a C12 unsaturated or saturated aliphatic acid or biologically compatible salt may be provided.
  • In another embodiment according to the present disclosure, a pesticidal composition is provided, comprising: one or more pesticidal agents; and one or more unsaturated C4-C10 aliphatic acids or agriculturally compatible salts thereof having at least one unsaturated C—C bond. In some other embodiments, a pesticidal composition comprising one or more pesticidal agents at one or more saturated C4-C10 aliphatic acids or agriculturally compatible salts thereof are provided. In some embodiments, the one or more saturated or unsaturated C4-C10 aliphatic acids produce a synergistic effect on the pesticidal activity of the pesticidal composition in comparison to the pesticidal activity of the pesticidal agent alone and are present in a respective synergistically active concentration ratio between about 1:15000 and 15000:1, more particularly between about 1:5000 and 5000:1, and further particularly between about 1:2000 and 2000:1. In some such embodiments, a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof may be provided. In some further such embodiments, a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof may be provided. In a further embodiment, a method of synergistically enhancing the pesticidal activity of at least one pesticidal active ingredient adapted to control at least one target pest organism is provided, comprising: providing at least one pesticidal active ingredient active for said at least one target pest organism; adding a synergistically effective concentration of at least one unsaturated or saturated C4-C10 aliphatic acid or an agriculturally acceptable salt thereof to provide a synergistic pesticidal composition; mixing said synergistic pesticidal composition with at least one formulation component comprising a surfactant to form a synergistic pesticidal concentrate; diluting said synergistic pesticidal concentrate with water to form a synergistic pesticidal emulsion; and applying said synergistic pesticidal emulsion at a pesticidally effective concentration and rate to control said at least one target pest organism. In some such embodiments, a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof may be provided. In some further such embodiments, a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof may be provided.
  • In some embodiments, the synergistic pesticidal composition may comprise a ratio of the concentrations by weight of said pesticidal active ingredient and said at least one saturated or unsaturated C4-C10 aliphatic acid or agriculturally compatible salts thereof is between about at least one of: 1:20,000 and 20,000:1, 1:15000 and 15000:1, 1:10,000 and 10,000:1, 1:5000 and 5000:1, 1:2500 and 2500:1, 1:2000 and 2000:1, 1:1500 and 1500:1, 1:1000 and 1000, 1:750 and 750:1, 1:500 and 500:1, 1:400 and 400:1, 1:300 and 300:1, 1:250 and 250:1, 1:200 and 200:1, 1:150 and 150:1, 1:100 and 100:1, 1:90 and 90:1, 1:80 and 80:1, 1:70 and 70:1, 1:60 and 60:1, 1:50 and 50:1, 1:40 and 40:1, 1:30 and 30:1, 1:25 and 25:1, 1:20 and 20:1, 1:15 and 15:1, 1:10 and 10:1, 1:9 and 9:1. 1:8 and 8:1, 1:7 and 7:1, 1:6 and 6:1, 1:5 and 5:1, 1:4 and 4:1, 1:3 and 3:1, 1:2 and 2:1, 1:1.5 and 1.5:1, and 1.25 and 1.25:1. In a particular such embodiment, the concentration ratios of the pesticidal active ingredient and said at least one C4-C10 saturated or unsaturated aliphatic acid or an agriculturally compatible salt thereof in the synergistic pesticidal composition are advantageously chosen so as to produce a synergistic effect against at least one target pest or pathogen. In some embodiments, the concentration ratios of the pesticidal active ingredient(s) and at least one C11 unsaturated or saturated aliphatic acid or agriculturally compatible salts thereof in the synergistic pesticidal composition may be advantageously chosen so as to produce a synergistic effect against at least one target pest or pathogen. In some further embodiments, the concentration ratios of the pesticidal active ingredient(s) and at least one C11 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof in the synergistic pesticidal composition may be advantageously chosen so as to produce a synergistic effect against at least one target pest or pathogen. In some embodiments, the synergistic pesticidal composition comprises a pesticidal active ingredient, and a C4-C10 unsaturated aliphatic acid which comprises at least one of: a trans-unsaturated C—C bond and a cis-unsaturated C—C bond. In a further such embodiment, the C4-C10 unsaturated aliphatic acid comprises at least one of: a trans-2, trans-3, trans-4, trans-5, trans-6, trans-7, trans-8, and trans-9 unsaturated bond. In yet another embodiment, a synergistic pesticidal composition is provided comprising a pesticidal active ingredient and a C4-C10 unsaturated aliphatic acid comprising at least one of: a cis-2, cis-3, cis-4, cis-5, cis-6, cis-7, cis-8, and cis-9 unsaturated bond. In some such embodiments, the pesticidal composition comprises a C11 unsaturated aliphatic acid or agriculturally compatible salt thereof, comprising at least one of: a trans-2, trans-3, trans-4, trans-5, trans-6, trans-7, trans-8, trans-9, trans-10, a cis-2, cis-3, cis-4, cis-5, cis-6, cis-7, cis-8, cis-9, and cis-10 unsaturated bond. In some further such embodiments, the pesticidal composition comprises a C12 unsaturated aliphatic acid or agriculturally compatible salt thereof, comprising at least one of: a trans-2, trans-3, trans-4, trans-5, trans-6, trans-7, trans-8, trans-9, trans-10, a cis-2, cis-3, cis-4, cis-5, cis-6, cis-7, cis-8, cis-9, and cis-10 unsaturated bond. In some embodiments, the synergistic pesticidal composition may comprise at least one C4-C10 saturated aliphatic acid, such as one or more of hexanoic, heptanoic, octanoic, nonanoic and decanoic acid, for example. In some further embodiments, the synergistic pesticidal composition may additionally comprise at least one second C4-C10 saturated or unsaturated aliphatic acid. In some further embodiments, the pesticidal composition may additionally comprise at least one second C11 or C12 unsaturated or saturated aliphatic acid, or agriculturally compatible salt thereof.
  • In some embodiments, the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise a naturally occurring aliphatic acid, such as may be present in, or extracted, fractionated or derived from a natural plant or animal material, for example. In one such embodiment, the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise one or more naturally occurring aliphatic acids provided in a plant extract or fraction thereof. In another such embodiment, the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise one or more naturally occurring aliphatic acids provided in an animal extract or product, or fraction thereof. In one such embodiment, the at least one C4-C10 saturated or unsaturated alphatic acid may comprise a naturally occurring aliphatic acid comprised in a plant oil extract, such as one or more of coconut oil, palm oil, palm kernel oil, corn oil, or fractions or extracts therefrom. In another such embodiment, the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise a naturally occurring aliphatic acid comprised in an animal extract or product, such as one or more of cow's milk, goat's milk, beef tallow, and/or cow or goat butter, or fractions or extracts thereof for example. In a particular embodiment, at least one C4-C10 saturated aliphatic acid may be provided in an extract or fraction of one or more plant oil extract, such as one or more of coconut oil, palm oil, palm kernel oil, corn oil, or fractions or extracts therefrom. In some further embodiments, the pesticidal composition may comprise at least one C11 or C12 saturated or unsaturated aliphatic acid provided in an extract or fraction of one or more plant or animal materials.
  • In some embodiments, the synergistic pesticidal composition exhibits a synergistic inhibition of growth of at least one target pest organism. In some embodiments, the synergistic pesticidal composition comprises a pesticidally effective concentration of the pesticidal active ingredient, and the one or more C4-C10 saturated or unsaturated aliphatic acid. In some further embodiments, the synergistic pesticidal composition comprises a pesticidal active ingredient, and a synergistic concentration of the one or more C4-C10 saturated or unsaturated aliphatic acid. In some embodiments, the synergistic pesticidal composition has a FIC Index (fractional inhibitory concentration index value) of less than 1 according to a growth inhibition assay for inhibition of growth of at least one target pest or pathogen organism. In some embodiments, the synergistic pesticidal composition has a FIC Index value of less than 0.75. In a further embodiment, the synergistic pesticidal composition has a FIC Index value of 0.5 or less. In some embodiments, the synergistic pesticidal composition has a synergistic efficacy factor, or Synergy Factor (comparing synergistic efficacy relative to expected additive (non-synergistic) efficacy according to the Colby Formula, or Loewe's Formula, or other accepted synergy determination method) of: at least 1.01, and more particularly at least 1.1, and further more particularly at least 1.5, and yet further more particularly at least 2, and more particularly at least 5, and yet more particularly at least 10, for example. In some such embodiments, the one or more saturated or unsaturated aliphatic acid may comprise a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof. In some further such embodiments, the one or more saturated or unsaturated aliphatic acid may comprise a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • In some embodiments, the pesticidal active ingredient may comprise at least one of a chemical pesticide and a naturally-derived pesticidal oil or extract. In a further aspect, the pesticidal active ingredient may comprise at least one of: a fungicide, nematicide, insecticide, acaricide, herbicide, and bactericide. In any such embodiments, the synergistic pesticidal composition may comprise one or more C4-C10 saturated or unsaturated aliphatic acid having at least one carboxylic group, and which may be linear or branched. In some embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a linear monocarboxylic acid. In some embodiments, the C4-C10 unsaturated aliphatic acid may comprise one or more of cis and trans isomers. In an embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may be unsubstituted or substituted. In some embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a substituent, such as a hydroxy, amino, carbonyl, aldehyde, acetyl, phosphate, or methyl substituent, for example. In one such embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise at least one of a 2-, 3-, 4-, 8-, or 10-substituted aliphatic acid. In one such embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a hydroxy aliphatic acid. In one particular such embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a 2-hydroxy, 3-hydroxy, or 4-hydroxy aliphatic acid. In one embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise an amino aliphatic acid. In one particular such embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a 3-amino aliphatic acid. In a further embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise a methyl and/or ethyl substituted aliphatic acid. In a particular such embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise at least one of a 2-methyl, 3-methyl, 4-methyl, 2-ethyl, or 2,2-diethyl substituted aliphatic acid, for example. In some embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise an unsaturated aliphatic acid which may be mono-unsaturated or polyunsaturated, i.e. containing one, two or more unsaturated carbon-carbon (C—C) bonds respectively. In some embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise an unsaturated aliphatic acid with at least one of: a trans-unsaturated C—C bond, a cis-unsaturated C—C bond, and a plurality of conjugated unsaturated C—C bonds. In some such embodiments, the one or more saturated or unsaturated aliphatic acid may comprise a C11 unsaturated or saturated aliphatic acid. In some further such embodiments, the one or more saturated or unsaturated aliphatic acid may comprise a C12 unsaturated or saturated aliphatic acid.
  • In some further embodiments, the one or more C4-C10 (including C4, C5, C6, C7, C8, C9 or C10) saturated or unsaturated aliphatic acid may comprise at least one of: a trans-hexenoic acid, a cis-hexenoic acid, a hexa-dienoic acid, a hexynoic acid, a trans-heptenoic acid, a cis-heptenoic acid, a hepta-dienoic acid, a heptynoic acid, a trans-octenoic acid, a cis-octenoic acid, an octa-dienoic acid, an octynoic acid, a trans-nonenoic acid, a cis-nonenoic acid, a nona-dienoic acid, a nonynoic acid, a trans-decenoic acid, a cis-decenoic acid, a deca-dienoic acid, and a decynoic acid. In another embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may comprise at least one of: a trans-hexenoic acid, a cis-hexenoic acid, a hexa-dienoic acid other than 2,4-hexadienoic acid, a hexynoic acid, a trans-heptenoic acid, a cis-heptenoic acid, a hepta-dienoic acid, a heptynoic acid, a trans-octenoic acid, a cis-octenoic acid, an octa-dienoic acid, an octynoic acid, a trans-nonenoic acid, a cis-nonenoic acid, a nona-dienoic acid, a nonynoic acid, a trans-decenoic acid, a cis-decenoic acid, a deca-dienoic acid, and a decynoic acid. In some embodiments, the one or more unsaturated aliphatic acid may comprise at least one of a C11 or C12 unsaturated aliphatic acid, such as a cis-undecenoic, trans-undecanoic, cis-dodecenoic, trans-dodecenoic, undeca-dienoic, dodeca-dienoic, undecynoic, or dodecynoic acid, for example.
  • In some further embodiments, the one or more C4-C10 (including C4, C5, C6, C7, C8, C9 or C10) saturated or unsaturated aliphatic acid may comprise at least one of: hexanoic, heptanoic, octanoic, nonanoic and decanoic acid. In some embodiments, the one or more saturated or unsaturated aliphatic acid may comprise at least one of undecanoic or dodecanoic acid.
  • In some embodiments, the synergistic pesticidal composition may comprise one or more agriculturally compatible or acceptable salts of a one or more C4-C10 saturated or unsaturated aliphatic acid. In one such embodiment, such agriculturally compatible or acceptable salts may comprise one or more of potassium, sodium, calcium, aluminum, other suitable metal salts, ammonium, and other agriculturally acceptable salts of one or more C4-C10 saturated or unsaturated aliphatic acids, for example. In another embodiment, the synergistic pesticidal composition may comprise one or more C4-C10 saturated or unsaturated aliphatic acid or a biologically compatible salt thereof, wherein said salt comprises at least one of an agriculturally, aquatic life, or mammal-compatible salt, for example. In some embodiments, the pesticidal composition may comprise one or more agriculturally compatible or acceptable salts of one or one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • However, in some other embodiments, the synergistic pesticidal composition may comprise a pesticidal active ingredient and a one or more C4-C10 saturated or unsaturated aliphatic acid, wherein the C4-C10 unsaturated aliphatic acid comprises at least one unsaturated C—C bond and wherein a ratio of the concentrations of said pesticidal active ingredient and said C4-C10 unsaturated aliphatic acid is between about 1:15000 and 15000:1, more particularly between about 1:5000 and 5000:1, and further particularly between about 1:2000 and 2000:1. In one such embodiment, the one or more C4-C10 saturated or unsaturated aliphatic acid may exclude agriculturally acceptable salts or other salt forms of the one or more C4-C10 saturated or unsaturated aliphatic acids. In a particular such embodiment, the synergistic pesticidal composition may exclude such salts for desired applications for which the acid forms of the one or more C4-C10 saturated or unsaturated aliphatic acids may be preferred. In one such application, it is known that accumulation of an undesirably high concentration of salts in some soils can be detrimental to the productivity or fertility of the soil, such as in particular salt sensitive soil applications, for example. Accordingly, in some embodiments, specifically excluding salt forms of the one or more C4-C10 saturated or unsaturated aliphatic acids may be particularly desirable. In some such embodiments, the pesticidal composition may comprise one or more C11 or C12 saturated or unsaturated aliphatic acid. In another embodiment, the synergistic pesticidal composition may comprise a pesticidal active ingredient and at least one C4-C10 saturated aliphatic acid, such as at least one of hexanoic, heptanoic, octanoic, nonanoic and decanoic acid, for example. In an alternative embodiment, the synergistic pesticidal composition may comprise a pesticidal active ingredient and at least one C4-C10 unsaturated aliphatic acid but explicitly excluding 2,4-hexadienoic acid. In some such embodiments, the one or more saturated or unsaturated aliphatic acid may comprise a C11 unsaturated or saturated aliphatic acid. In some further such embodiments, the one or more saturated or unsaturated aliphatic acid may comprise a C12 unsaturated or saturated aliphatic acid.
  • In some embodiments of the present disclosure, a synergistic pesticidal composition may comprise at least one C4-C10 saturated or unsaturated aliphatic acid and at least one pesticidal active ingredient selected from the list comprising:
      • A) Respiration inhibitors selected from:
        • inhibitors of complex III at Qo site: azoxystrobin (II-1), coumethoxy-strobin, coumoxystrobin, dimoxystrobin (II-2), enestroburin, fenamin-strobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin (II-3), kresoxim-methyl (II-4), metominostrobin, orysastrobin (II-5), picoxystrobin (II-6), pyraclostrobin (II-7), pyrame-tostrobin, pyraoxystrobin, trifloxystrobin (II-8), 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneamino-oxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, fenamidone;
        • Inhibitors of complex III at Qi site: cyazofamid, amisulbrom, [(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)-amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbony-loxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpro-panoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol5-ylmethoxy)-4-methoxy-pyridine-2-carbon-yl]amino]-6-methyl-4,9-dioxol,5-dioxonan-7-yl] 2-methylpropanoate; (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenyl-methyl)-1,5-dioxonan-7-yl 2-methylpropanoate;
        • Inhibitors of complex II: benodanil, benzovindiflupyr (II-9), bixafen (II-10), boscalid (II-11), carboxin, fenfuram, fluopyram (II-12), flutolanil, fluxapyroxad (II-13), furametpyr, isofetamid, isopyrazam (II-14), mepronil, oxycarboxin, penflufen (II-15), penthiopyrad (II-16), sedaxane (II-17), tecloftalam, thifluzamide, N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide, 3-(difluorome-thyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1,3-dimethyl-pyrazole-4-carboxamide, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide;
        • Other respiration inhibitors: diflumetorim, (5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluorometh-ylpyridin-2-yloxy)-phenyl]-ethyl}-amine; binapacryl, dinobuton, dinocap, fluazinam (II-18); ferimzone; fentin salts such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin (II-19); and silthiofam;
      • B) Sterol biosynthesis inhibitors (SBI fungicides) selected from:
        • C14 demethylase inhibitors (DMI fungicides): azaconazole, bitertanol, bromuconazole, cyproconazole (II-20), difenoconazole (II-21), diniconazole, diniconazole-M, epoxiconazole (II-22), fenbuconazole, fluquinconazole (II-23), flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole (II-24), myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole (II-25), prothioconazole (II-26), simeconazole, tebuconazole (II-27), tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole; imazalil, pefurazoate, prochloraz, triflumizol; fenarimol, nuarimol, pyrifenox, triforine, [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol;
        • Delta14-reductase inhibitors: aldimorph, dodemorph, dodemorphacetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
        • Inhibitors of 3-keto reductase: fenhexamid;
      • C) Nucleic acid synthesis inhibitors selected from:
        • phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam) (II-38), ofurace, oxadixyl;
        • others nucleic acid inhibitors: hymexazole, octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;
      • D) Inhibitors of cell division and cytoskeleton selected from:
        • tubulin inhibitors: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl (II-39); 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine
        • other cell division inhibitors: diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone (II-40), pyriofenone;
      • E) Inhibitors of amino acid and protein synthesis selected from:
        • methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil, mepanipyrim, Pyrimethanil (II-41);
        • protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
      • F) Signal transduction inhibitors selected from:
        • MAP/histidine kinase inhibitors: fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
        • G protein inhibitors: quinoxyfen;
      • G) Lipid and membrane synthesis inhibitors selected from:
        • Phospholipid biosynthesis inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; propamocarb, propamocarb-hydrochloride;
        • lipid peroxidation inhibitors: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
        • phospholipid biosynthesis and cell wall deposition: dimethomorph (II-42), flumorph, mandipropamid (II-43), pyrimorph, benthiavalicarb, iprovalicarb, valifenalate, N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
        • acid amide hydrolase inhibitors: oxathiapiprolin;
      • H) Inhibitors with Multi Site Action selected from:
        • inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride (II-44), basic copper sulfate, sulfur;
        • thio- and dithiocarbamates: ferbam, mancozeb (II-45), maneb, metam, metiram (II-46), propineb, thiram, zineb, ziram;
        • organochlorine compounds: anilazine, Chlorothalonil (II-47), captafol, captan, folpet, dichlofluanid, dichlorophen, hexachlorobenzene, pentachlorophenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
        • guanidines and others: guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon, 2,6-dimethyl-1H,5H-[1,4]dithii-no[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone (II-48);
      • I) Cell wall synthesis inhibitors selected from:
        • inhibitors of glucan synthesis: validamycin, polyoxin B;
        • melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamid, dicyclomet, fenoxanil;
      • J) Plant defence inducers selected from:
        • acibenzolar-S-methyl, probenazole, isotianil, tiadinil, prohexadione-calcium; fosetyl, fosetyl-aluminum, phosphorous acid and its salts (II-49);
      • K) Unknown mode of action selected from: bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover, flusulfamide, flutianil, methasulfocarb, nitrapyrin, nitrothal-isopropyl, oxathiapiprolin, tolprocarb, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, 2-[3,5-bis-(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yl-oxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]-ethanone, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen-4-one, N-(cyclo-propylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methyl formamidine, N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, methoxyacetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester, 3-[5-(4-meth-ylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole), N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide, 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole, 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phe-nyl)-isoxazol-5-yl]-2-prop2-ynyloxy-acetamide, ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate, tertbutyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]-amino]oxymethyl]-2-pyridyl]carbamate, pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, 2-[2-[(7,8-dif-luoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-qui-nolyl)oxy]phenyl]propan-2-ol, 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline; Fenpicoxamid, florylpicoxamid;
      • L) Antifungal biopesticides selected from: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus pumilus (II-50), Bacillus subtilis (II-51), Bacillus subtilis var. amyloliquefaciens (II-52), Candida oleophila I-82, Candida saitoana, Clonostachys rosea f. catenulata, also named Gliocladium catenulatum, Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Metschnikowia fructicola, Microdochium dimerum, Phlebiopsis gigantea, Pseudozyma flocculosa, Pythium oligandrum DV74, Reynoutria sachlinensis, Talaromyces flavus VI 17b, Trichoderma asperellum SKT-1, T. atroviride LC52, T. harzianum T-22, T. harzianum TH 35, T. harzianum T-39; T. harzianum and T. viride, T. harzianum ICC012 and T. viride ICC080; T. polysporum and T. harzianum; T. stromaticum, T. virens GL-21, T. viride, T. viride TV1, Ulocladium oudemansii HRU3;
      • M) Growth regulators selected from: abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassino-lide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride) (II-54), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium, II-55), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid, trinex-apac-ethyl and uniconazole;
      • N) Herbicides selected from:
        • acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, me-tolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
        • amino acid derivatives: bilanafos, glyphosate, glufosinate, sulfosate;
        • aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
        • Bipyridyls: diquat, paraquat;
        • (thio)carbamates: asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
        • cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;
        • dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin;
          • diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen; —hydroxybenzonitriles: bomoxynil, dichlobenil, ioxynil;
          • imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
        • phenoxy acetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
        • pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, pyridate;
        • pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
        • sulfonyl ureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuronethyl, chlorsulfuron, cinosul-furon, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nico-sulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosul-furon, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1-((2-chloro-6-propyl-imidazo[1,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimethoxy-pyrimidin-2-yl)urea;
        • triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
        • ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;
        • other acetolactate synthase inhibitors: bispyribac-sodium, cloransulammethyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribam-benz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, py-roxsulam;
        • other herbicides: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, bicyclopyrone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfa-mide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenoxy]-pyri-din-2-yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2-cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol, 4-amino-3-chloro-6-(4-chlorophenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid methyl ester, and 4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)-pyridine-2-carboxylic acid methyl ester;
      • O) Insecticides selected from:
        • organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phos-phamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
        • carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenox-ycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
        • pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zetacypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
        • insect growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, dif-lubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
        • nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran, flupyradifurone, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1-2-chloro-thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1,3,5]triazinane;
        • nicotinic acetylcholine receptor disruptors or allosteric modulators (IRAC Goup 5): spinosyn (including but not limited to spinosyns A, D, B, C, E, F, G, H, J, and other spinosyn isolates from Saccharopolyspora spinosa culture), spinosad (comprising primarily spinsyns A and D), and derivatives or substituents thereof (including but not limited to tetracyclic and pentacyclic spinosyn derivatives, aziridine spinosyn derivatives, C-5,6 and/or C-13,14 substituted spinosyn derivatives); spinetoram (including but not limited to XDE-175-J, XDE-175-L or other O-ethyl substituted spinosyn derivatives); butenyl-spinosyn and derivatives or substituents thereof (such as isolates from Saccharopolyspora pogona culture);
        • bioinsecticides including but not limited to Bacillus thuriengiensis, Burkholderia spp, Beauveria bassiana, Metarhizium anisoptiae, Paecilomyces fumosoroseus, and baculoviruses (including but not limited to granuloviruses and nucleopolyhedroviruses);
        • GABA antagonist compounds: endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1-(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl-1H-pyrazole-3-carbothioic acid amide;
        • mitochondrial electron transport inhibitor (METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
        • METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;
        • Uncouplers: chlorfenapyr;
        • oxidative phosphorylation inhibitors: cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
        • moulting disruptor compounds: cryomazine;
        • mixed function oxidase inhibitors: piperonyl butoxide;
        • sodium channel blockers: indoxacarb, metaflumizone;
        • ryanodine receptor inhibitors: chlorantraniliprole, cyantraniliprole, fluben-diamide, N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyra-zole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-car-boxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanyli-dene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide; N-[4,6-di-bromo-2-[(di-2-propyl-lambda-4-sulfanyl-idene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
        • others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, pyrifluquinazon, 1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]-methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl] cyclopropaneacetic acid ester; fluensulfone, fluoroalkenyl thioethers; and
      • P) ribonucleic acid (RNA) and associated compounds including double-stranded RNA (dsRNA), microRNA (miRNA) and small interfering RNA (siRNA); bacteriophages.
  • In some such embodiments, the synergistic pesticidal composition may comprise one or more pesticidal active ingredient, such as selected from the list above, and one or more C11 unsaturated or saturated aliphatic acid or agriculturally acceptable salt thereof. In some further such embodiments, the synergistic pesticidal composition may comprise one or more pesticidal active ingredient, such as selected from the list above, and one or more C12 unsaturated or saturated aliphatic acid or agriculturally acceptable salt thereof.
  • In some embodiments, synergistic pesticidal compositions may be provided, where the pesticidal active ingredient comprises at least one pesticidal natural oil selected from: neem oil, karanja oil, clove oil, clove leaf oil, peppermint oil, spearmint oil, mint oil, cinnamon oil, thyme oil, oregano oil, rosemary oil, geranium oil, lime oil, lavender oil, anise oil, lemongrass oil, tea tree oil, apricot kernel oil, bergamot oil, carrot seed oil, cedar leaf oil, citronella oil, clove bud oil, coriander oil, coconut oil, eucalyptus oil, evening primrose oil, fennel oil, ginger oil, grapefruit oil, nootkatone(+), grapeseed oil, lavender oil, marjoram oil, pine oil, scotch pine oil, and/or garlic oil and/or components, derivatives and/or extracts of one or more pesticidal natural oil, or a combination thereof. In some further embodiments, synergistic pesticidal compositions may be provided which comprise additional active components other than the principal one or more pesticidal active ingredients, wherein such additional active components may comprise one or more additional efficacies and/or synergistic effects on the pesticidal efficacy of the composition, such as but not limited to adjuvants, synergists, agonists, activators, or combinations thereof, for example. In one such embodiment, such additional active components may optionally comprise naturally occurring compounds or extracts or derivatives thereof. In other embodiments, the pesticidal active ingredient may comprise at least one organic, certified organic, US Department of Agriculture (“USDA”) National Organic Program compliant (“NOP-compliant”) such as may be included in the US Environmental Protection Agency FIFRA 25b, list of ingredients published dated December 2015 by the US EPA entitled “Active Ingredients Eligible for Minimum Risk Pesticide Products”, the US EPA FIFRA 4a list published August 2004 entitled “List 4A—Minimal Risk Inert Ingredients” or the US EPA FIFRA 4b list published August 2004 entitled “List 4B—Other ingredients for which EPA has sufficient information”, for example, Organic Materials Review Institute listed (“OMRI-listed”) or natural pesticidal active ingredient, for example.
  • In some embodiments, the pesticidal active ingredient may comprise at least one of: neem oil, karanja oil and extracts or derivatives thereof. In further exemplary such embodiments, the pesticidal active ingredient may comprise at least one extract or active component of neem oil or karanja oil, such as but not limited to: azadirachtin, azadiradione, azadirone, nimbin, nimbidin, salannin, deacetylsalannin, salannol, maliantriol, gedunin, karanjin, pongamol, or derivatives thereof, for example.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • Exemplary embodiments are illustrated in referenced figures of the drawings. It is intended that the embodiments and figures disclosed herein are to be considered illustrative rather than restrictive.
  • FIG. 1 illustrates general carbonyl alkene structures (1), (2) and (3) associated with an exemplary C4-C10 unsaturated aliphatic acid, or agriculturally acceptable salt thereof, according to an embodiment of the present disclosure.
  • FIG. 2 illustrates an exemplary 96 well microtiter plate showing a color transition of a resazurin dye between colors indicating absence and presence of growth of a representative pest or pathogen, in accordance with a synergistic growth inhibition assay according to an embodiment of the present disclosure.
  • FIGS. 3-5 illustrate the observed survival rate (percent of original insects still surviving) for Trichoplusia ni (cabbage looper caterpillar) over time for in-vitro testing on a modified McMorran artificial diet to which treatments of Pylon® insecticide (containing chlorfenapyr as the pesticidal active ingredient) and exemplary unsaturated aliphatic acids (and salts) alone are shown in comparison with the corresponding survival rates for treatments with a synergistic pesticidal composition combining Pylon® insecticide with each of the exemplary unsaturated aliphatic acids (and salts) at three concentrations (shown in FIGS. 3, 4 , and 5 respectively), according to an embodiment of the present invention.
    •  DETAILED DESCRIPTION OF SEVERAL EMBODIMENTS
  • Throughout the following description specific details are set forth in order to provide a more thorough understanding to persons skilled in the art. However, well known elements may not have been shown or described in detail to avoid unnecessarily obscuring the disclosure. Accordingly, the description and drawings are to be regarded in an illustrative, rather than a restrictive, sense.
    • Definitions
  • Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the invention, suitable methods and materials are described herein.
  • All applications, publications, patents and other references, citations cited herein are incorporated by reference in their entirety. In case of conflict, the specification, including definitions, will control.
  • As used herein, the singular forms “a”, “and,” and “the” include plural referents unless the context clearly indicates otherwise.
  • As used herein, all numerical values or numerical ranges include integers within such ranges and fractions of the values or the integers within ranges unless the context clearly indicates otherwise. Thus, for example, reference to a range of 90-100%, includes 91%, 92%, 93%, 94%, 95%, 95%, 97%, etc., as well as 91.1%, 91.2%, 91.3%, 91.4%, 91.5%, etc., 92.1%, 92.2%, 92.3%, 92.4%, 92.5%, etc., and so forth.
  • As used herein, “plant” embraces individual plants or plant varieties of any type of plants, in particular agricultural, silvicultural and ornamental plants.
  • As used herein, the terms “pest” or “pests” or grammatical equivalents thereof, are understood to refer to organisms, e.g., including pathogens, that negatively affect a host or other organism—such as a plant or an animal—by colonizing, damaging, attacking, competing with them for nutrients, infesting or infecting them, as well as undesired organisms that infest human structures, dwellings, living spaces or foodstuffs. Pests include but are not limited to fungi, weeds, nematodes, acari, and arthropods, including insects, arachnids and cockroaches. It is understood that the terms “pest” or “pests” or grammatical equivalents thereof can refer to organisms that have negative effects by infesting plants and seeds, and commodities such as stored grain.
  • As used herein, the terms “pesticide” or “pesticidal” or grammatical equivalents thereof, are understood to refer to any composition or substance that can be used in the control of any agricultural, natural environmental, human or other animal pathogenic, and domestic/household pests. The terms “control” or “controlling” are meant to include, but are not limited to, any killing, inhibiting, growth regulating, or pestistatic (inhibiting or otherwise interfering with the normal life cycle of the pest) activities of a composition against a given pest. These terms include for example sterilizing activities which prevent the production or normal development of seeds, ova, sperm or spores, cause death of seeds, sperm, ova or spores, or otherwise cause severe injury to the genetic material. Further activities intended to be encompassed within the scope of the terms “control” or “controlling” include preventing larvae from developing into mature progeny, modulating the emergence of pests from eggs including preventing eclosion, degrading the egg material, suffocation, interfering with mycelial growth, reducing gut motility, inhibiting the formation of chitin, disrupting mating or sexual communication, preventing feeding (antifeedant) activity, and interfering with location of hosts, mates or nutrient-sources. The term “pesticide” includes fungicides, herbicides, nematicides, insecticides and the like. The term “pesticide” encompasses, but is not limited to, naturally occurring compounds as well as so-called “synthetic chemical pesticides” having structures or formulations that are not naturally occurring, where pesticides may be obtained by various means including, but not limited to, extraction from biological sources, chemical synthesis of the compound, and chemical modification of naturally occurring compounds obtained from biological sources.
  • As used herein, the terms “insecticidal” and “acaridical” or “aphicidal” or grammatical equivalents thereof, are understood to refer to substances having pesticidal activity against organisms encompassed by the taxonomical classification of root term and also to refer to substances having pesticidal activity against organisms encompassed by colloquial uses of the root term, where those colloquial uses may not strictly follow taxonomical classifications. The term “insecticidal” is understood to refer to substances having pesticidal activity against organisms generally known as insects of the phylum Arthropoda, class Insecta. Further as provided herein, the term is also understood to refer to substances having pesticidal activity against other organisms that are colloquially referred to as “insects” or “bugs” encompassed by the phylum Arthropoda, although the organisms may be classified in a taxonomic class different from the class Insecta. According to this understanding, the term “insecticidal” can be used to refer to substances having activity against arachnids (class Arachnida), in particular mites (subclass Acari/Acarina), in view of the colloquial use of the term “insect.” The term “acaridical” is understood to refer to substances having pesticidal activity against mites (Acari/Acarina) of the phylum Arthropoda, class Arachnida, subclass Acari/Acarina. The term “aphicidal” is understood to refer to substances having pesticidal activity against aphids (Aphididae) of the phylum Arthopoda, class Insecta, family Aphididae. It is understood that all these terms are encompassed by the term “pesticidal” or “pesticide” or grammatical equivalents. It is understood that these terms are not necessarily mutually exclusive, such that substances known as “insecticides” can have pesticidal activity against organisms of any family of the class Insecta, including aphids, and organisms that are encompassed by other colloquial uses of the term “insect” or “bug” including arachnids and mites. It is understood that “insecticides” can also be known as acaricides if they have pesticidal activity against mites, or aphicides if they have pesticidal activity against aphids.
  • As used herein, the terms “control” or “controlling” or grammatical equivalents thereof, are understood to encompass any pesticidal (killing) activities or pestistatic (inhibiting, repelling, deterring, and generally interfering with pest functions to prevent the damage to the host plant) activities of a pesticidal composition against a given pest. Thus, the terms “control” or “controlling” or grammatical equivalents thereof, not only include killing, but also include such activities as repelling, deterring, inhibiting or killing egg development or hatching, inhibiting maturation or development, and chemisterilization of larvae or adults. Repellant or deterrent activities may be the result of compounds that are poisonous, mildly toxic, or non-poisonous to pests, or may act as pheromones in the environment.
  • As used herein, the term “pesticidally effective amount” generally means the amount of the inventive mixtures or of compositions comprising the mixtures needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target pest organism. The pesticidally effective amount can vary for the various mixtures/compositions used in the invention. A pesticidally effective amount of the mixtures/compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mod+e of application, and the like. As used herein, where a range of values is provided, it is understood that each intervening value, to the tenth of the unit of the lower limit unless the context clearly dictates otherwise, between the upper and lower limit of that range and any other stated or intervening value within that stated range is encompassed within embodiments of the invention. The upper and lower limits of these smaller ranges may independently define a smaller range of values, and it is to be understood that these smaller ranges are intended to be encompassed within embodiments of the invention, subject to any specifically excluded limit in the stated range.
  • In one embodiment according to the present disclosure, a synergistic pesticidal composition comprises a C4-C10 unsaturated aliphatic acid (or agriculturally acceptable salt thereof), the and at least one pesticidal active ingredient. In some embodiments, the effective dose of the pesticidal active ingredient when used in combination with the one or more C4-C10 saturated or unsaturated aliphatic acid is lower than the effective dose of the pesticidal active ingredient when used alone (i.e. a smaller amount of pesticidal active can still control pests when used in a synergistic composition together with the one or more C4-C10 saturated or unsaturated aliphatic acid). In some embodiments, a pesticidal active ingredient that is not effective against a particular species of pest can be made effective against that particular species when used in a synergistic composition together with one or more C4-C10 saturated or unsaturated aliphatic acid. In some such embodiments, the pesticidal composition may comprise a C11 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof. In some further such embodiments, the pesticidal composition may comprise a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • Without being bound by any particular theory, it is believed that the one or more C4-C10 saturated or unsaturated aliphatic acids according to some embodiments of the present disclosure act as cell permeabilizing agents, and when combined with a suitable pesticidal active ingredient, may desirably facilitate the entry of the pesticidal active ingredient into the cells of a target pest or pathogen, thereby desirably providing for a synergistic activity of such a synergistic pesticidal composition. All eukaryotic cell membranes, including for example fungal cell membranes and the cell membranes of insects and nematodes are biochemically similar in that they all comprise a lipid bilayer which is comprised of phospholipids, glycolipids and sterols, as well as a large number of proteins (Cooper & Hausmann 2013). The amphipathic structure of the lipid bilayer and the polarity of membrane proteins restricts passage of extracellular compounds across the membrane and allows compartmentalization of internal organelles from the intracellular environment. Without being bound by theory, it is believed that the one or more C4-C10 saturated or unsaturated aliphatic acids according to some embodiments disclosed herein will act as cell permeabilizing agents, and when combined with a suitable pesticidal active ingredient may desirably act to enhance the entry of the active ingredient (such as but not limited to fungicidal, insecticidal, acaricidal, molluscicidal, bactericidal and nematicidal actives) into the cells and/or into the intracellular organelles or intracellular bodies of a target pest or pathogen (such as but not limited to fungi, insects, acari, mollusks, bacteria and nematodes, respectively), for example.
  • In a further embodiment, without being bound by theory, it is believed that the size and/or polarity of many pesticidal molecules prevents and/or limits the pesticidal active ingredient from crossing the cellular membrane, but that the addition of one or more C4-C10 saturated or unsaturated aliphatic acid in accordance with some embodiments of the present disclosure may desirably compromise or provide for the disturbance of the pest cell membrane's lipid bilayer integrity and protein organization such as to create membrane gaps, and/or increase the membrane fluidity, such as to allow the pesticidal active to more effectively enter the cell and/or intracellular organelles of the pest cells, for example. In some such embodiments, the pesticidal composition may comprise a C11 unsaturated aliphatic acid or agriculturally compatible salt thereof. In some further such embodiments, the pesticidal composition may comprise a C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • In another aspect, without being bound to any particular theory, it is believed that the one or more C4-C10 saturated or unsaturated aliphatic acids, or agriculturally acceptable salts thereof, (and in some additional embodiments, alternatively a C11 or C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof). In some further such embodiments, the pesticidal composition may comprise a C12 unsaturated aliphatic acid or agriculturally compatible salt thereof according to some embodiments of the present disclosure act as at least one of a potentiator, synergist, adjuvant and/or agonist when combined with a suitable pesticidal active ingredient, thereby desirably providing for a synergistic activity of such a synergistic pesticidal composition against a target pest or pathogen.
  • In some embodiments according to the present disclosure, a synergistic pesticidal composition accordingly to the present invention comprises one or more C4-C10 saturated or unsaturated aliphatic acid, or agriculturally acceptable salts thereof (and in some additional embodiments, alternatively a C11 or C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof), as an exemplary cell permeabilizing agent, in combination with a pesticide. In some embodiments, the synergistic composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof), as an exemplary cell permeabilizing agent, in combination with a fungicide. In some embodiments, the synergistic composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof), as an exemplary cell permeabilizing agent, in combination with a nematicide. In some embodiments, the synergistic composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof), as an exemplary cell permeabilizing agent, in combination with an insecticide.
  • In one such embodiment, without being bound to a particular theory, it is believed that the one or more C4-C10 saturated or unsaturated aliphatic acid (and in some additional embodiments, alternatively a C11 or C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof) may act as a cellular membrane delivery agent, so as to improve the entry of and/or bioavailability or systemic distribution of a pesticidal active ingredient within a target pest cell and/or within a pest intracellular organelle, such by facilitating the pesticidal active ingredient in passing into the mitochondria of the pest cells, for example. In some other embodiments, without being bound by a particular theory, the one or more C4-C10 saturated or unsaturated aliphatic acid may further provide for synergistic interaction with one or more additional compounds provided as part of the pesticidal composition, such as an additional one or more C4-C10 saturated aliphatic acid, or one or more C4-C10 unsaturated aliphatic acid, or one or more additional active ingredients or adjuvants, so as to provide for synergistic enhancement of a pesticidal effect provided by the at least one pesticidal active ingredient, for example.
  • In another aspect, without being bound to any particular theory, it is believed that the one or more C4-C10 saturated or unsaturated aliphatic acids (or agriculturally acceptable salts thereof) according to some embodiments of the present disclosure act as at least one of a potentiator, synergist, adjuvant and/or agonist when combined with a suitable pesticidal ingredient, thereby desirably providing for a synergistic activity of such a synergistic pesticidal composition against a target pest or pathogen. In some additional embodiments, such synergistic pesticidal composition may alternatively comprise a C11 or C12 unsaturated or saturated aliphatic acid or agriculturally compatible salt thereof.
  • Without being bound by any particular theory, in some embodiments of the present invention, it is believed that the one or more C4-C10 saturated or unsaturated aliphatic acids act to compromise or alter the integrity of the lipid bilayer and protein organization of cellular membranes in target pest organisms. Further, it is also believed that in some embodiments one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action that is dependent upon interaction with one or more components of the cellular membrane of a target pest. In some such embodiments, one or more C4-C10 saturated or unsaturated aliphatic acids may be particularly adapted for combining to form a synergistic pesticidal composition, demonstrating synergistic efficacy, with pesticidal actives which have a mode of action dependent on interaction with a cellular membrane protein. In one such embodiment, the cellular membrane protein may comprise one or more cytochrome complexes, such as a cytochrome bel complex or a cytochrome p450 complex, for example. Accordingly, in one aspect, synergistic pesticidal compositions according to some embodiments of the present invention may desirably be selected to comprise one or more C4-C10 saturated or unsaturated aliphatic acids, and one or more pesticidal active having a pesticidal mode of action that is dependent upon interaction with one or more components of the cellular membrane of a target pest, such as a cellular membrane protein, for example. In one aspect, one or more C11 or C12 saturated or unsaturated aliphatic acids is provided in combination with one or more pesticidal active having a pesticidal mode of action that is dependent upon interaction with one or more components of the cellular membrane of a target pest, such as a cellular membrane protein, for example. In a particular embodiment, one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by inhibiting one or more receptor sites) the cellular membrane cytochrome be 1 complex (also known as the cytochrome complex III), such as fungicidal actives collectively referred to as Group 11 actives by the Fungicide Resistance Action Committee (FRAC), including e.g. azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, mandestrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim-methyl trifloxystrobin, dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, or pyribencar. In one such embodiment, a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with the cellular cytochrome bel complex, such as a strobilurin pesticidal active. In alternative such embodiments, the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • In another particular embodiment, one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by inhibiting one or more receptor sites) the cellular membrane cytochrome p450 complex, such as to inhibit sterol biosynthesis, as is the case with exemplary fungicidal actives collectively referred to as FRAC Group 3 actives, including e.g. triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, or prothioconazole. In one such embodiment, a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with the cellular cytochrome p450 complex, such as an azole or triazole pesticidal active, for example. In alternative such embodiments, the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • In another particular embodiment, one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by inhibiting one or more receptor sites) the cellular membrane, such as to uncouple oxidative phosphorylation, as is the case with exemplary insecticidal actives collectively referred to as Group 13 actives by the Insecticide Resistance Action Committee (IRAC), including e.g. quinoxyfen or proquinazid. In one such embodiment, a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with the cellular membrane, such as a pyrrole insecticidal active, an example of which is chlorfenapyr. In alternative such embodiments, the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • In another particular embodiment, one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by disrupting and/or allosterically modulating one or more receptor sites) the cellular membrane, such as to disrupt one or more nicotinic acetylcholine receptor sites (such as Site 1), as is the case with exemplary insecticidal actives collectively referred to as Group 5 actives by the Insecticide Resistance Action Committee (IRAC). Such IRAC Group 5 actives include, for example: spinosyn (including but not limited to spinosyns A, D, B, C, E, F, G, H, J, and other spinosyn isolates from Saccharopolyspora spinosa culture), spinosad (comprising primarily spinsyns A and D), and derivatives or substituents thereof (including but not limited to tetracyclic and pentacyclic spinosyn derivatives, aziridine spinosyn derivatives, C-5,6 and/or C-13,14 substituted spinosyn derivatives); spinetoram (including but not limited to XDE-175-J, XDE-175-L or other O-ethyl substituted spinosyn derivatives); butenyl-spinosyn and derivatives or substituents thereof (such as isolates from Saccharopolyspora pogona culture). In one such embodiment, a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with the cellular membrane, such as a spinosyn or spinosyn derivative insecticidal active, examples of which may include Spinosad and spinetoram. In alternative such embodiments, the synergistic pesticidal composition may comprise one or more C11 or C12 saturated or unsaturated aliphatic acids, substituents, or salts thereof.
  • Without being bound by any particular theory, in some further embodiments of the present invention, it is believed that one or more C4-C10 saturated or unsaturated aliphatic acids act to compromise or alter the integrity of the lipid bilayer and protein organization of cellular membranes in target pest organisms, and by so doing are effective to increase at least one of the fluidity and permeability of a cellular membrane of a target pest organism, which may desirably increase permeability and/or transport of a pesticidal active through the cellular membrane, for example. Further, it is also believed that in some embodiments one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action that is dependent upon transport across one or more cellular membrane of a target pest, such as to interact with a target site inside a cell or an intracellular organelle of the target pest. In some such embodiments, a synergistic pesticidal composition according to an embodiment of the present invention, demonstrating synergistic efficacy, may comprise one or more C4-C10 saturated or unsaturated aliphatic acid, and one or more pesticidal active having a mode of action dependent on transport across a cellular membrane. Accordingly, in one aspect, synergistic pesticidal compositions according to some embodiments of the present invention may desirably be selected to comprise one or more C4-C10 saturated or unsaturated aliphatic acids, and one or more pesticidal active having a pesticidal mode of action that is dependent upon interaction with a target site within a cell or intracellular organelle of a target pest, such as a cellular membrane protein, for example. In alternative such embodiments, the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • In a particular embodiment, one or more C4-C10 saturated or unsaturated aliphatic acids are particularly adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives having a pesticidal mode of action interacting with (such as by inhibiting one or more receptors) at a target site across a cellular membrane of a target pest, such as fungicidal actives collectively referred to as FRAC Group 9 and Group 12 actives, for example, including e.g. cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil or fludioxonil. In one such embodiment, a synergistic pesticidal composition may be selected comprising one or more C4-C10 saturated or unsaturated aliphatic acid and a pesticidal active having a pesticidal mode of action interacting with a target site within a cellular membrane of a target pest, such as one or more of an anilinopyrimidine such as cyprodinil, and a phenylpyrrole such as fludioxonil, for example. In alternative such embodiments, the synergistic pesticidal composition comprises one or more C11 or C12 saturated or unsaturated aliphatic acids.
  • Without being bound by any particular theory, in some yet further embodiments of the present invention, it is believed that one or more C4-C10 saturated or unsaturated aliphatic acids act to compromise or alter the integrity of the lipid bilayer and protein organization of cellular membranes in target pest organisms, and by so doing are effective to increase at least one of the fluidity and permeability of a cellular membrane of a target pest organism, which may desirably increase permeability and/or transport of a pesticidal active through the cellular membrane, for example. Further, it is also believed that in some alternative embodiments one or more C4-C10 unsaturated aliphatic acids having unsaturated C—C bonds at one or more of the second (2-), third (3-) and terminal ((n−1)-) locations in the aliphatic acid carbon chain may be desirably adapted for combination to form synergistic pesticidal compositions according to embodiments of the invention, which demonstrate synergistic efficacy, with pesticidal actives. In some particular such embodiments, one or more C4-C10 aliphatic acids comprising an unsaturated C—C bond at one or more of the 2-,3- and (n−1)-locations (wherin n is the number of carbons in the unsaturated aliphatic acid) may desirably be adapted for forming synergistic pesticidal compositions in combination with one or more pesticidal active having a pesticidal mode of action that is dependent upon interaction with a cellular membrane component of a target pest, or dependent upon transport across one or more cellular membrane of a target pest (such as to interact with a target site inside a cell or an intracellular organelle of the target pest). In some such embodiments, a synergistic pesticidal composition according to an embodiment of the present invention, demonstrating synergistic efficacy, may comprise one or more C4-C10 unsaturated aliphatic acid having an unsaturated C—C bond at one or more of the 2-, 3- and terminal ((n−1)-) locations in the aliphatic acid carbon chain, and one or more pesticidal active having a mode of action dependent on interaction with a target pest cellular membrane component, or on transport across a target pest cellular membrane. In alternative such embodiments, the synergistic pesticidal composition comprises one or more C11 or C12 unsaturated aliphatic acids having an unsaturated C—C bond at one or more of the 2-, 3- and terminal ((n−1)-).
  • In some embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises an aliphatic carbonyl alkene. In some embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises at least one C4-C10 unsaturated aliphatic acid having at least one carboxylic group and at least one unsaturated C—C bond. In another embodiment, the C4-C10 unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises at least two C4-C10 unsaturated aliphatic acids having at least one carboxylic group and at least one unsaturated C—C bond. In yet another embodiment, the C4-C10 unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises at least one carboxylic acid group and at least one of a double or triple C—C bond. In a further embodiment, a synergistic pesticidal composition is provided comprising at least one pesticidal active ingredient, and at least one C4-C10 unsaturated aliphatic acid (or agriculturally acceptable salt thereof) having at least one carboxylic acid group and at least one unsaturated C—C bond, in combination with at least one C4-C10 saturated aliphatic acid (or agriculturally acceptable salt thereof). In yet another embodiment, the C4-C10 saturated or unsaturated aliphatic acid may be provided as a plant extract or oil, or fraction thereof, containing the at least one C4-C10 saturated or unsaturated aliphatic acid, for example, or in further embodiments, containing the one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • In some embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) comprises an aliphatic carbonyl alkene having one of the general structures (1), (2) or (3), as shown in FIG. 1 . In further embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid may additionally comprise a C11 or C12 saturated or unsaturated aliphatic acid, and may comprise an aliphatic carbonyl alkene having one of the general structures (1), (2) or (3) as shown in FIG. 1 . In some embodiments, the C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid may additionally comprise at least one substituent selected from the list comprising: hydroxy, alkyl and amino substituents. In some exemplary embodiments, the at least one substituent may comprise at least one of: 2-hydroxy, 3-hydroxy, 4-hydroxy, 8-hydroxy, 10-hydroxy, 12-hydroxy, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2,2-diethyl, 2-amino, 3-amino, and 4-amino substituents, for example. In some embodiments, the C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid may comprise an agriculturally acceptable salt form of any of the above-mentioned aliphatic acids. In some embodiments, the composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) and a fungicidal active ingredient. In some embodiments, the effective dose of the fungicidal active ingredient when used in combination with the one or more C4-C10 saturated or unsaturated aliphatic acid is lower than the effective dose of the fungicidal active ingredient when used alone (i.e. a smaller amount of fungicidal active can still control fungi when used in a composition together with the one or more C4-C10 saturated or unsaturated aliphatic acid). In some embodiments, a fungicidal active ingredient that is not effective against a particular species of fungi (such as at a particular concentration that is below a lower limit of efficacy for a particular fungi, or for a particular species of fungi which may be at least partially resistant or tolerant to the particular fungicidal active ingredient when applied alone) can be made effective against that particular species when used in a composition together with one or more C4-C10 saturated or unsaturated aliphatic acid, or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • In some embodiments, the composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) and a nematicidal active ingredient. In some embodiments, the effective dose of the nematicidal active ingredient when used in combination with the one or more C4-C10 saturated or unsaturated aliphatic acid is lower than the effective dose of the nematicidal active ingredient when used alone (i.e. a smaller amount of nematicidal active can still control nematodes when used in a composition together with the one or more C4-C10 saturated or unsaturated aliphatic acid). In some embodiments, a nematicidal active ingredient that is not effective against a particular species of nematode (such as at a particular concentration that is below a lower limit of efficacy for a particular nematode, or for a particular species of nematode which may be at least partially resistant or tolerant to the particular nematicidal active ingredient when applied alone) can be made effective against that particular species when used in a composition together with one or more C4-C10 saturated or unsaturated aliphatic acid, or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid.
  • In some embodiments, the composition comprises one or more C4-C10 saturated or unsaturated aliphatic acid (or agriculturally acceptable salt thereof) and an insecticidal active ingredient. In some embodiments, the effective dose of the insecticidal active ingredient when used in combination with the one or more C4-C10 saturated or unsaturated aliphatic acid is lower than the effective dose of the insecticidal active ingredient when used alone (i.e. a smaller amount of insecticidal active can still control insects, to an exemplary desired degree of control, when used in a composition together with the one or more C4-C10 saturated or unsaturated aliphatic acid). In some embodiments, the aliphatic acid may further comprise one or more C11 or C12 saturated or unsaturated aliphatic acid. In some embodiments, an insecticidal active ingredient that is not effective against a particular species of insect (such as at a particular concentration that is below a lower limit of efficacy for a particular insect, or for a particular species of insect which may be at least partially resistant or tolerant to the particular insecticidal active ingredient when applied alone) can be made effective against that particular species when used in a composition together with one or more C4-C10 saturated or unsaturated aliphatic acid, or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid. In further embodiments, the one or more C4-C10 saturated or unsaturated aliphatic acid (or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid) may desirably provide for a synergistic increased efficacy of at least one of an acaricidal, molluscicidal, bactericidal or virucidal active ingredient such that the composition is pesticidally effective against one or more of an acari, mollusk, bacterial or viral pest, for example.
  • In some embodiments, a pesticidal composition is provided comprising at least one C4-C10 saturated or unsaturated aliphatic acid (or in some further embodiments at least one C11 or C12 saturated or unsaturated apliphatic acid) and an insecticidal pesticidal active ingredient, comprising at least one nicotinic acetylcholine receptor disruptors. In one such embodiment, the insecticidal active ingredient may comprise at least one or more of: a spinosyn (including but not limited to spinosyns A, D, B, C, E, F, G, H, J, and other spinosyn isolates from Saccharopolyspora spinosa culture), spinosad (comprising primarily spinsyns A and D), and derivatives or substituents thereof (including but not limited to tetracyclic and pentacyclic spinosyn derivatives, aziridine spinosyn derivatives, C-5,6 and/or C-13,14 substituted spinosyn derivatives); a spinetoram (including but not limited to XDE-175-J and XDE-175-L); and a butenyl-spinosyn and derivatives or substituents thereof (such as isolates from Saccharopolyspora pogona culture). In a particular such embodiment, a pesticidal composition is provided, comprising at least one C4-C10 saturated or unsaturated aliphatic acid (or in some further embodiments at least one C11 or C12 saturated or unsaturated apliphatic acid) and at least one of spinosyn A and spinosyn D. In a further such embodiment, the at least one spinosyn comprises spinosad. In some embodiments, the pesticidal composition comprises a synergistic pesticidal composition. In some particular embodiments, the synergistic pesticidal composition desirably provides a synergistic efficacy to control at least one insect pest.
  • In some further embodiments, a method of reducing a risk of resistance of at least one target pest to at least one pesticidal active ingredient is provided, the method comprising:
      • selecting at least one C4-C10 saturated or unsaturated aliphatic acid, or suitable salt thereof, which when applied to said at least one target pest as a pesticidal composition comprising said at least one pesticidal active ingredient and said at least one C4-C10 saturated or unsaturated aliphatic acid, or suitable salt thereof, is effective to provide a synergistic efficacy against said at least one target pest, relative to the application of said at least one pesticidal active ingredient alone; and applying said at least one pesticidal composition to a locus proximate to said at least one target pest.
  • In some embodiments, the at least one C4-C10 saturated or unsaturated aliphatic acid, or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid, may comprise a naturally occurring aliphatic acid, such as may be present in, or extracted, fractionated or derived from a natural plant or animal material, for example. In one such embodiment, the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise one or more naturally occurring aliphatic acids provided in a plant extract or fraction thereof. In another such embodiment, the at least one C4-C10 saturated or unsaturated aliphatic acid may comprise one or more naturally occurring aliphatic acids provided in an animal extract or product, or fraction thereof. In one such embodiment, the at least one C4-C10 saturated or unsaturated alphatic acid may comprise a naturally occurring aliphatic acid comprised in a plant oil extract, such as one or more of coconut oil, palm oil, palm kernel oil, corn oil, or fractions or extracts therefrom. In another such embodiment, the at least one C4-C10 saturated or unsaturated alphatic acid may comprise a naturally occurring aliphatic acid comprised in an animal extract or product, such as one or more of cow's milk, goat's milk, beef tallow, and/or cow or goat butter, or fractions or extracts thereof for example. In a particular embodiment, at least one C4-C10 saturated or unsaturated aliphatic acid may be provided as a component of one or more natural plant or animal material, or extract or fraction thereof. In a particular such embodiment, at least one C4-C10 saturated aliphatic acid may be provided in an extract or fraction of one or more plant oil extract, such as one or more of coconut oil, palm oil, palm kernel oil, corn oil, or fractions or extracts therefrom.
  • In some embodiments, an emulsifier or other surfactant may used in preparing pesticidal compositions according to aspects of the present disclosure. Suitable surfactants can be selected by one skilled in the art. Examples of surfactants that can be used in some embodiments of the present disclosure include, but are not limited to sodium lauryl sulfate, saponin, ethoxylated alcohols, ethoxylated fatty esters, alkoxylated glycols, ethoxylated fatty acids, ethoxylated castor oil, glyceryl oleates, carboxylated alcohols, carboxylic acids, ethoxylated alkylphenols, fatty esters, sodium dodecylsulfide, other natural or synthetic surfactants, and combinations thereof. In some embodiments, the surfactant(s) are non-ionic surfactants. In some embodiments, the surfactant(s) are cationic or anionic surfactants. In some embodiments, a surfactant may comprise two or more surface active agents used in combination. The selection of an appropriate surfactant depends upon the relevant applications and conditions of use, and selection of appropriate surfactants are known to those skilled in the art.
  • In one aspect, a pesticidal composition according to some embodiments of the present disclosure comprises one or more suitable carrier or diluent component. A suitable carrier or diluent component can be selected by one skilled in the art, depending on the particular application desired and the conditions of use of the composition. Commonly used carriers and diluents may include ethanol, isopropanol, isopropyl myristate, other alcohols, water and other inert carriers, such as but not limited to those listed by the EPA as a Minimal Risk Inert Pesticide Ingredients (4A) (the list of ingredients published dated December 2015 by the US EPA FIFRA 4a list published August 2004 entitled “List 4A—Minimal Risk Inert Ingredients”) or, for example, Inert Pesticide Ingredients (4B) (the US EPA FIFRA 4b list published August 2004 entitled “List 4B—Other ingredients for which EPA has sufficient information”) or under EPA regulation 40 CFR 180.950 dated May 24, 2002, each of which is hereby incorporated herein in its entirety for all purposes including for example, citric acid, lactic acid, glycerol, castor oil, benzoic acid, carbonic acid, ethoxylated alcohols, ethoxylated amides, glycerides, benzene, butanol, 1-propanol, hexanol, other alcohols, dimethyl ether, and polyethylene glycol.
  • In one embodiment according to the present disclosure, a method of enhancing the efficacy of a pesticide is provided. In one aspect, a method of enhancing the efficacy of a fungicide is provided. In another aspect, a method of enhancing the efficacy of a nematicide is provided. In a further aspect, a method of enhancing the efficacy of an insecticide is provided.
  • In one such embodiment, the method comprises providing a synergistic pesticidal composition comprising a pesticidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid (or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid) and exposing a pest to the resulting synergistic composition. In a particular exemplary embodiment, without being bound by any particular theory, the at least one C4-C10 saturated or unsaturated aliphatic acid may desirably be functional as a cell permeabilizing or cell membrane disturbing agent. In one aspect, the method comprises providing a fungicidal composition comprising a fungicidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid and exposing a fungus to the resulting synergistic composition. In another aspect, the method comprises providing a nematicidal composition comprising a nematicidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid and exposing a nematode to the resulting synergistic composition. In a further aspect, the method comprises providing an insecticidal composition comprising an insecticidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid and exposing an insect to the resulting synergistic composition.
  • In one embodiment according to the present disclosure, the at least one C4-C10 saturated or unsaturated aliphatic acid (or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid) provided in a pesticidal composition comprises an unsaturated aliphatic carbonyl alkene. In a particular such embodiment, without being bound by any particular theory, the at least one C4-C10 unsaturated aliphatic acid may desirably be functional as a cell permeabilizing or cell membrane disturbing agent. In one such embodiment, the cell permeabilizing agent comprises a carbonyl alkene having the general structure (1), (2) or (3), as shown in FIG. 1 . In a further embodiment, the cell permeabilizing agent comprises at least one unsaturated aliphatic acid comprising at least one carboxylic group and having at least one unsaturated C—C bond.
  • In one exemplary embodiment, a method comprises providing a synergistic pesticidal composition comprising a pesticidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid (or in further embodiments, with one or more C11 or C12 saturated or unsaturated aliphatic acid) which is functional as a cell permeabilizing agent, and exposing a pest to the synergistic pesticidal composition to increase the amount of the pesticidal active ingredient that enters cells of the pest. In some such embodiments, the pesticidal active is a fungicide and the pest is a fungus, and without being bound by a particular theory, the at least one C4-C10 saturated or unsaturated aliphatic acid cell permeabilizing agent allows the fungicide to pass more easily through the fungal cell walls and membranes, and/or intracellular membranes. In some such embodiments, the pesticide is a nematicide and the pest is a nematode, and without being bound by a particular theory, the at least one C4-C10 saturated or unsaturated aliphatic acid cell permeabilizing agent allows the nematicide to pass more easily through the nematode cell and intracellular membranes. In some such embodiments, the pesticide is an insecticide, and without being bound by a particular theory, the at least one C4-C10 saturated or unsaturated aliphatic acid cell permeabilizing agent allows the insecticide to pass more easily through insect cuticle, chitin membrane, or cell or intracellular membranes.
  • In some embodiments, in addition to the actual synergistic action with respect to pesticidal activity, certain synergistic pesticidal compositions according to embodiments of the present disclosure can also desirably have further surprising advantageous properties. Examples of such additional advantageous properties may comprise one or more of: more advantageous degradability in the environment; improved toxicological and/or ecotoxicological behaviour such as reduced aquatic toxicity or toxicity to beneficial insects, for example.
  • In a further aspect, for any of the embodiments described above or below providing for a synergistic pesticidal composition comprising at least one pesticidal active and one or more C4-C10 saturated or unsaturated aliphatic acid or salt thereof, in an alternative embodiment, the synergistic pesticidal composition may alternatively comprise at least one pesticidal active and one or more C11 saturated or unsaturated aliphatic acid or salt thereof. In another aspect, for any of the embodiments described above providing for a synergistic pesticidal composition comprising at least one pesticidal active and one or more C4-C10 saturated or unsaturated aliphatic acid or salt thereof, in an alternative embodiment, the synergistic pesticidal composition may alternatively comprise at least one pesticidal active and one or more C12 saturated or unsaturated aliphatic acid or salt thereof.
    • EXPERIMENTAL METHODS
  • In accordance with an embodiment of the present disclosure, the combination of at least one C4-C10 saturated or unsaturated aliphatic acid (and in some embodiments alternatively at least one C11 or C12 saturated or unsaturated aliphatic acid) and a pesticidal active ingredient produces a synergistic pesticidal composition demonstrating a synergistic pesticidal effect. In some embodiments, the synergistic action between the pesticidal active ingredient, and the at least one C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid components of the pesticidal compositions according to embodiments of the present disclosure was tested using a Synergistic Growth Inhibition Assay, which is derived from and related to a checkerboard assay as is known in the art for testing of combinations of antimicrobial agents. In the Synergistic Growth Inhibition Assay used in accordance with some embodiments of the present disclosure, multiple dilutions of combinations of pesticidal active ingredient and at least one C4-C10 saturated or unsaturated aliphatic acid agents are tested in individual cells for inhibitory activity against a target pest or pathogenic organism. In one such embodiment, the combinations of pesticidal active ingredient and C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents may preferably be tested in decreasing concentrations. In a further such embodiment, the combinations of pesticidal active ingredient and C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents may be tested in increasing concentrations. These multiple combinations of the pesticidal active ingredient and at least one C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents may be prepared in 96-well microtiter plates. In one such embodiment, the Synergistic Growth Inhibition Assay then comprises rows which each contain progressively decreasing concentrations of the pesticidal active ingredient and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents to test for the MIC of the agents in combination at which growth of the target pest or pathogen is inhibited. Thus, each well of the microtiter plate is a unique combination of the two agents, at which inhibitory efficacy of the combination against the target pest or pathogen can be determined.
  • A method of determining and quantifying synergistic efficacy is by calculation of the “Fractional Inhibitory Concentration Index” or FIC index, as is known in the art for determining synergy between two antibiotic agents (see for example M. J. Hall et al., “The fractional inhibitory concentration (FIC) index as a measure of synergy”, J Antimicrob Chem., 11 (5):427-433, 1983, for example). In one embodiment according to the present disclosure, for each row of microtiter cells in the Synergistic Growth Inhibition Assay, the FIC index is calculated from the lowest concentration of the pesticidal active ingredient and one or more C4-C10 saturated or unsaturated aliphatic acid agents necessary to inhibit growth of a target pest or pathogen. The FIC of each component is derived by dividing the concentration of the agent present in that well of the microtiter plate by the minimal inhibitory concentration (MIC) needed of that agent alone to inhibit growth of the target pest or pathogen. The FIC index is then the sum of these values for both agents in that well of the microtiter plate. The FIC index is calculated for each row as follows:

  • FICindex=MICa/MICA+MICb/MICB
  • where MICa, MICb are the minimal inhibitory concentration (MIC) of compounds A and B, respectively, when combined in the mixture of the composition, and MICA, MICB are the MIC of compounds A and B, respectively, when used alone. Fractional inhibitory concentration indices may then used as measure of synergy. When the lowest FIC index obtained in a microtiter plate in this way is less than 1 (FICindex<1), the combination of the pesticidal active ingredient and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents exhibits synergism, and indicates a synergistic pesticidal composition. When the FIC index is equal to 1, the combination is additive. FIC index values of greater than 4 are considered to exhibit antagonism.
  • In a particular embodiment, when the FIC index is equal or less than 0.5, the combination of the pesticidal active ingredient and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents exhibits strong synergism. For example, in one embodiment, an FIC index of 0.5 may correspond to a synergistic pesticidal composition comprising a pesticidal agent at ¼ of its individual MIC, and one or more (or alternatively C11 or C12) C4-C10 saturated or unsaturated aliphatic acid agent at ¼ of its individual MIC.
  • In some embodiments of the present disclosure, the exemplary Synergistic Growth Inhibition Assay was conducted starting with an initial composition comprising a pesticidal active ingredient agent (compound A) at its individual MIC and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent (compound B) at its individual MIC in the first well of a row on a 96 well microtiter plate. Then, serial dilutions of these initial compositions in successive wells in the row of the microtiter plate were used to assay the pesticidal composition under the same conditions to determine the concentration of the composition combining the two agents corresponding to the microtiter well in which growth inhibition of the target pest or organism ceases. The minimal inhibitory concentrations of each individual pesticidal active ingredient agent (compound A) and each of the one or more C4-C10 saturated or unsaturated aliphatic acid agent (as compound B) were determined in parallel with the compositions combining the two agents.
  • In some embodiments, Fusarium oxysporum was used as a representative pest organism or pathogen to determine synergy in pesticidal compositions comprising a pesticidal active ingredient agent (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent (compound B). Resazurin dye (also known as Alamar blue dye) was used as an indicator to determine the presence of growth or inhibition of growth of Fusarium oxysporum in the wells of the 96 well microtiter plates used in the exemplary Synergistic Growth Inhibition Assay. In addition to the color change of the resazurin dye in the presence of growth of the Fusarium oxysporum, an optical or visual examination of the microtiter well may also be made to additionally determine the presence of growth or inhibition of growth of the Fusarium oxysporum.
  • In other embodiments, Botrytis cinerea was used as a representative pest organism or pathogen to determine synergy in pesticidal compositions comprising a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent (compound B). Similarly to as described above, Resazurin was used as an indicator of growth or inhibition of growth of Botrytis cinerea in the exemplary Synergistic Growth Inhibition Assay. In addition to the color change of the resazurin, an optical or visual examination of the microtiter well may also be made to additionally determine the presence of growth or inhibition of growth of the Botrytis cinerea.
  • In further embodiments, Sclerotinia sclerotiorum was used as a representative pest organism or pathogen to determine synergy in pesticidal compositions comprising a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent (compound B). Similarly to as described above, Resazurin was used as an indicator of growth or inhibition of growth of Sclerotinia sclerotiorum in the exemplary Synergistic Growth Inhibition Assay. In addition to the color change of the resazurin, an optical or visual examination of the microtiter well may also be made to additionally determine the presence of growth or inhibition of growth of the Sclerotinia sclerotiorum.
  • Alternatively, other suitable representative pest or pathogen organisms may be used to determine synergy of combinations of pesticidal active ingredient agents and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents in accordance with embodiments of the present disclosure. For example, other representative fungal pathogens may be used, such as but not limited to Leptosphaeria maculans, Sclerotinia spp. and Verticillium spp. In yet other examples, suitable non-fungal representative pests or pathogens may be used, such as insect, acari, nematode, bacterial, viral, mollusc or other pests or pathogens suitable for use in an MIC growth inhibition assay test method. All examples detailed below were tested according to the exemplary Synergistic Growth Inhibition Assay described above, using routine techniques for MIC determination known to those of skill in the art. Stock solutions of the pesticidal active ingredient agents and the one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents were initially prepared in 100% dimethylsulfoxide (“DMSO”), and diluted to 10% DMSO using sterile potato dextrose broth (PDB) before further serial dilution to obtain the test solution concentrations for use in the microtiter plate wells, with exceptions in particular experimental examples noted in detail below. Accordingly, the maximum concentration of DMSO in the test solutions was limited to 10% DMSO or less, which was separately determined to be non-inhibitory to the growth of the representative fungal pests used in the test.
  • A culture of the representative fungal pathogen, namely Fusarium oxysporum, Botrytis cinerea, or Sclerotinia sclerotiorum, for example, is grown to exponential phase in potato dextrose broth (PDB). A 20 uL aliquot of homogenized mycelium from the culture is transferred to a well of a 96 well microtiter plate, and incubated for a period between 1 day and 7 days (depending on the pathogen and the particular assay reagents, as noted in the example descriptions below) with 180 uL of the test solution comprising the pesticidal and aliphatic acid agents in combination at a range of dilutions, to allow the mycelium to grow. Following the incubation period, 10 uL of resazurin dye is added to each well and the color in the solution is observed and compared to the color of the test solution at the same concentrations in wells without mycelial culture innoculum to control for effects of the test solution alone. The resazurin dye appears blue for wells with only the initial 20 uL culture where growth has been inhibited, and appears pink for wells where mycelial growth has occurred, as shown in FIG. 2 , where the transition from blue to pink color can be clearly seen in each of the uppermost 4 rows of microtiter wells (labelled as 1-4 in FIG. 2 ) as the concentration of the pesticidal and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agents in the test solution decreases from left to right. In addition to the color change of the resazurin dye, growth or absence of growth of the mycelial culture is also observed visually or optically.
  • In accordance with this assay method, the Minimum Inhibitory Concentration is the lowest concentration at which growth is inhibited, and corresponds to the microtiter well in which the dye color is the same as for the control without culture and without growth, and/or in which a visual and/or optical inspection confirm that growth is inhibited.
    • EXPERIMENTAL EXAMPLES Example 1: Growth Inhibition of Fusarium oxysporum by Pyraclostrobin in Combination with Several Exemplary C4-C10 Unsaturated Aliphatic Acids (or Agriculturally Acceptable Salts Thereof)
  • Sample Preparation:
  • 10 mg of pyraclostrobin (available from Santa Cruz Biotechnology of Dallas, Tex. as stock #229020) was dissolved in 10 mL dimethylsulfoxide (DMSO) and the resulting solution was diluted 2-fold in DMSO to give a concentration of 0.5 mg/mL. This solution was diluted 10-fold in potato dextrose broth (PDB) to give a concentration of 0.05 mg/mL in 10% DMSO/90% PDB. The solubility of pyraclostrobin in 10% DMSO/90% PDB was determined to be 0.0154 mg/mL using high performance liquid chromatography (HPLC).
  • A solution of (2E,4E)-2,4-hexadienoic acid, potassium salt, was prepared by dissolving 2 g of (2E,4E)-2,4-hexadienoic acid, potassium salt, in 20 mL of PDB which was diluted further by serial dilution in PDB. A solution of (2E,4E)-2,4-hexadienoic acid (available from Sigma-Aldrich as stock #W342904) was prepared by dissolving 20 mg of (2E,4E)-2,4-hexadienoic acid in 1 mL DMSO and adding 0.1 mL to 0.9 mL PDB resulting in a 2 mg/mL solution of (2E,4E)-2,4-hexadienoic acid in 10% DMSO/90% PDB which was diluted further by serial dilution in PDB.
  • A solution of trans-2-hexenoic acid (available from Sigma-Aldrich as stock #W316903) was prepared by dissolving 100 mg trans-2-hexenoic acid in 1 mL DMSO and adding 0.1 mL to 0.9 mL PDB resulting in a 10 mg/mL solution in 10% DMSO/90% PDB which was diluted further by serial dilution in PDB. A solution of trans-3-hexenoic acid (available from Sigma-Aldrich as stock #W317004) was prepared by adding 20 uL trans-3-hexenoic acid to 1980 uL PDB and the resulting solution was serially diluted in PDB. The density of trans-3-hexenoic acid was assumed to be 0.963 g/mL.
  • Combinations of pyraclostrobin and one or more exemplary C4-C10 saturated or unsaturated aliphatic acids (and agriculturally acceptable salts thereof) were prepared by adding 0.5 mL of 0.0308 mg/mL pyraclostrobin to 0.5 mL of 1.25 mg/mL (2E,4E)-2,4-hexadienoic acid, potassium salt, (combination 1), 0.5 mL of 0.25 mg/mL (2E,4E)-2,4-hexadienoic acid (combination 2), 0.5 mL of 0.625 mg/mL (2E,4E)-2,4-hexadienoic acid (combination 3), 0.5 mL of 1.25 mg/mL of trans-2-hexenoic acid (combination 4), or 0.5 mL of 0.6019 mg/mL trans-3-hexenoic acid (combination 5). Each combination was tested over a range of 2-fold dilutions in the Synergistic Growth Inhibition Assay detailed above, observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Table 1.
  • TABLE 1
    Growth inhibition of Fusarium oxysporum by pyraclostrobin in combination with several
    exemplary unsaturated aliphatic acids (or agriculturally acceptable salts thereof).
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0154
    (2E,4E)-2,4-hexadienoic 0.625
    acid, potassium salt
    (2E,4E)-2,4-hexadienoic 0.125
    acid
    Trans-2-hexenoic acid 0.3125
    Trans-3-hexenoic acid 0.3125
    1 Pyraclostrobin (2E,4E)-2,4-hexadienoic 0.00385 0.1563 40 0.50
    acid, potassium salt
    2 Pyraclostrobin (2E,4E)-2,4-hexadienoic 0.00385 0.03125 20 0.50
    acid
    3 Pyraclostrobin (2E,4E)-2,4-hexadienoic 0.001925 0.03906 8 0.44
    acid
    4 Pyraclostrobin Trans-2-hexenoic acid 0.00385 0.1563 40 0.75
    5 Pyraclostrobin Trans-3-hexenoic acid 0.00385 0.07813 20 0.50
    • Example 2: Growth Inhibition of Fusarium oxysporum by Fludioxonil in Combination with Several Exemplary Unsaturated Aliphatic Acids (or Agriculturally Acceptable Salts Thereof)
  • Sample Preparation:
  • 20 mg of fludioxonil (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China) was dissolved in 10 mL dimethylsulfoxide (DMSO) and the resulting solution was diluted 2-fold in DMSO to give a concentration of 1 mg/mL. This solution was diluted 10-fold in potato dextrose broth (PDB) to give a concentration of 0.1 mg/mL in 10% DMSO/90% PDB. The solubility of fludioxonil in 10% DMSO/90% PDB was determined to be 0.0154 mg/mL using HPLC.
  • A solution of (2E,4E)-2,4-hexadienoic acid, potassium salt, was prepared by dissolving 2 g of (2E,4E)-2,4-hexadienoic acid, potassium salt, in 20 mL of PDB which was diluted further by serial dilution in PDB. A solution of (2E,4E)-2,4-hexadienoic acid (available from Sigma-Aldrich as #W342904) was prepared by dissolving 20 mg of (2E,4E)-2,4-hexadienoic acid in 1 mL DMSO and adding 0.1 mL to 0.9 mL PDB resulting in a 2 mg/mL solution of (2E,4E)-2,4-hexadienoic acid in 10% DMSO/90% PDB which was diluted further by serial dilution in PDB.
  • A solution of trans-2-hexenoic acid (available from Sigma-Aldrich as stock #W316903) was prepared by dissolving 100 mg trans-2-hexenoic acid in 1 mL DMSO and adding 0.1 mL to 0.9 mL PDB resulting in a 10 mg/mL solution in 10% DMSO/90% PDB which was diluted further by serial dilution in PDB. A solution of trans-3-hexenoic acid (available from Sigma-Aldrich as stock #W317004) was prepared by adding 20 uL trans-3-hexenoic acid to 1980 uL PDB and the resulting solution was serially diluted in PDB. The density of trans-3-hexenoic acid was assumed to be 0.963 g/mL.
  • Combinations of compounds A and B as shown below in Table 2 were prepared by adding 0.5 mL of 9.63×10−4 mg/mL fludioxonil to each of 0.5 mL of 0.625 mg/mL (2E,4E)-2,4-hexadienoic acid, potassium salt, (combination 1), 0.5 mL of 0.25 mg/mL (2E,4E)-2,4-hexadienoic acid (combination 2), 0.5 mL of 0.625 mg/mL of trans-2-hexenoic acid (combination 3), and 0.5 mL of 0.6019 mg/mL trans-3-hexenoic acid (combination 4). Each combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Table 2.
  • TABLE 2
    Growth inhibition of Fusarium oxysporum by fludioxonil in combination with several
    exemplary unsaturated aliphatic acids (or agriculturally acceptable salts thereof).
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Fludioxonil 4.8125 × 10−4
    (2E,4E)-2,4-hexadienoic 0.625
    acid, potassium salt
    (2E,4E)-2,4-hexadienoic 0.125
    acid
    Trans-2-hexenoic acid 0.3125
    Trans-3-hexenoic acid 0.3125
    1 Fludioxonil (2E,4E)-2,4-hexadienoic 6.0188 × 10−5 0.03906 649 0.19
    acid, potassium salt
    2 Fludioxonil (2E,4E)-2,4-hexadienoic 6.0188 × 10−5 0.01563 260 0.25
    acid
    3 Fludioxonil Trans-2-hexenoic acid 1.2038 × 10−4 0.07813 649 0.5
    4 Fludioxonil Trans-3-hexenoic acid 1.2038 × 10−4 0.07813 649 0.5
    • Example 3: Growth Inhibition of Fusarium oxysporum by Fludioxonil in Combination with Several Exemplary Unsaturated Aliphatic Acids
  • Sample Preparation:
  • 20 mg fludioxonil (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China) was dissolved in 10 mL dimethylsulfoxide (DMSO) and the resulting solution was diluted 2-fold in DMSO to give a concentration of 1 mg/mL. This solution was diluted 10-fold in potato dextrose broth (PDB) to give a concentration of 0.1 mg/mL in 10% DMSO/90% PDB. The solubility of fludioxonil in 10% DMSO/90% PDB was determined to be 0.0154 mg/mL using HPLC.
  • Stock solutions of several exemplary C4-C10 unsaturated aliphatic acids as Compound B for testing individual MICs were prepared at 25 uL/mL in DMSO by adding 25 uL of each Compound B to 975 uL DMSO, followed by 10-fold dilution in PDB, for each of 3-octenoic acid (available from Sigma-Aldrich as stock #CDS000466), trans-2-octenoic acid (available from Sigma-Aldrich), 9-decenoic acid (available from Sigma-Aldrich as #W366005), 3-decenoic acid (available from Sigma-Aldrich as stock #CDS000299), and trans-2-decenoic acid (available from TCI America as stock #D0098).
  • For testing in combination with fludioxonil, solutions of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid were prepared at 0.78 uL/mL in DMSO by adding 3.125 uL of each Compound B to 2 mL of DMSO, followed by 2-fold dilution in DMSO to give 0.78 uL/mL. Solutions of 3-decenoic acid and trans-2-decenoic acid were prepared similarly, but applying a further 2-fold dilution in DMSO to give a concentration of 0.39 uL/mL in DMSO.
  • Each of these resulting stock solutions were then diluted 10-fold in PDB to give solutions of 0.078 uL/mL for each of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid, and to give solutions of 0.039 uL/mL for each of 3-decenoic acid and trans-2-decenoic acid, all in 10% DMSO/90% PDB. Combinations of the exemplary Compound B components with fludioxonil were prepared by adding 0.5 mL of 0.078 uL/mL of each of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid or 0.039 uL/mL of each of 3-decenoic acid and trans-2-decenoic acid, to 0.5 mL of 4.813×10−4 mg/mL fludioxonil obtained from serial dilution of 0.0154 mg/mL of fludioxonil in 10% DMSO/90% PDB, as prepared above, with PDB. The density of 3-octenoic acid was assumed to be 0.938 g/mL. The density of trans-2-octenoic acid was assumed to be 0.955 g/mL. The density of 3-decenoic acid was assumed to be 0.939 g/mL. The density of trans-2-decenoic acid was assumed to be 0.928 g/mL. The density of 9-decenoic acid was assumed to be 0.918 g/mL.
  • Each combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Table 3.
  • TABLE 3
    Growth inhibition of Fusarium oxysporum by fludioxonil in combination
    with several exemplary unsaturated aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Fludioxonil 2.4063 × 10−4
    3-Octenoic acid 0.1466
    Trans-2-octenoic acid 0.1492
    3-Decenoic acid 0.07336
    Trans-2-decenoic acid 0.03625
    9-Decenoic acid 0.07172
    1 Fludioxonil 3-Octenoic acid 1.2031 × 10−4 0.01832 152 0.63
    2 Fludioxonil Trans-2-octenoic acid 1.2031 × 10−4 0.01865 155 0.63
    3 Fludioxonil 3-Decenoic acid 1.2031 × 10−4 0.00917 76 0.63
    4 Fludioxonil Trans-2-decenoic acid 1.2031 × 10−4 0.00906 75 0.75
    5 Fludioxonil 9-Decenoic acid 1.2031 × 10−4 0.01793 149 0.75
    • Example 4: Growth Inhibition of Fusarium oxysporum by Thyme Oil in Combination in Combination with Several Exemplary Unsaturated Aliphatic Acids
  • Sample Preparation:
  • 12.5 mg of thyme oil (available from Sigma-Aldrich as stock #W306509) was dissolved in 1 g dimethylsulfoxide (DMSO) and the resulting solution was diluted 10-fold in PDB to give a concentration of 1.25 mg/mL 10% DMSO/90% PDB.
  • Stock solutions of several exemplary C4-C10 unsaturated aliphatic acids as Compound B for testing individual MICs were prepared at 25 μL/mL by adding 25 μL of each of 3-octenoic acid (available from Sigma-Aldrich as stock #CDS000466), trans-2-octenoic acid (available from Sigma-Aldrich as stock #CDS000466), 9-decenoic acid (available from Sigma-Aldrich as stock #W366005), 3-decenoic acid (available from Sigma-Aldrich as stock #CDS000299), and trans-2-decenoic acid (available from TCI America as stock #D0098), to 975 μL DMSO followed by 10-fold dilution in PDB.
  • Stock solutions of the exemplary C4-C10 unsaturated aliphatic acids as Compound B for testing in combination with thyme oil were prepared by adding 3.125 μL of each of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid, to 2 mL of DMSO followed by 2-fold dilution in DMSO to give a 0.78 L/mL concentration stock solution. Solutions of 3-decenoic acid and trans-2-decenoic acid were prepared similarly, but applying a further 2-fold dilution in DMSO to give a concentration of 0.39 μL/mL. Each of these resulting stock solutions were then diluted 10-fold dilution in PDB to give solutions of 0.078 μL/mL (for each of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid) and 0.039 L/mL (for 3-decenoic acid and trans-2-decenoic acid) in 10% DMSO/90% PDB.
  • Combinations of the exemplary Compound B components with thyme oil were prepared by adding 0.5 mL of 0.078 i/mL of each of 3-octenoic acid, trans-2-octenoic acid, and 9-decenoic acid or 0.039 μL/mL of each of 3-decenoic acid and trans-2-decenoic acid, to 0.5 mL of 1.25 mg/mL thyme oil in 10% DMSO/90% PDB. The density of 3-octenoic acid was assumed to be 0.938 g/mL. The density of trans-2-octenoic acid was assumed to be 0.955 g/mL. The density of 3-decenoic acid was assumed to be 0.939 g/mL. The density of trans-2-decenoic acid was assumed to be 0.928 g/mL. The density of 9-decenoic acid was assumed to be 0.918 g/mL
  • Each combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Table 4.
  • TABLE 4
    Growth inhibition of Fusarium oxysporum by thyme oil in combination
    in combination with several exemplary unsaturated aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Thyme oil 1.25
    3-Octenoic acid 0.14656
    Trans-2-octenoic acid 0.14922
    3-Decenoic acid 0.07336
    Trans-2-decenoic acid 0.03625
    9-Decenoic acid 0.07172
    1 Thyme oil 3-Octenoic acid 0.3125 0.01832 0.059 0.38
    2 Thyme oil Trans-2-octenoic acid 0.3125 0.01865 0.060 0.38
    3 Thyme oil 3-Decenoic acid 0.3125 0.00917 0.029 0.38
    4 Thyme oil Trans-2-decenoic acid 0.3125 0.00906 0.029 0.50
    5 Thyme oil 9-Decenoic acid 0.3125 0.01793 0.057 0.50
    • Example 5: Growth Inhibition of Botrytis cinerea by Neem Oil Limonoid Extract (Extracted from Cold-Pressed Neem Oil) and Fortune Aza Technical (Azadirachtin Extract) in Combination with Various Exemplary Unsaturated Aliphatic Acids
  • Sample Preparation:
  • An extract of limonoids was prepared from cold-pressed neem oil using solvent extraction with hexane and methanol to prepare a neem oil limonoid extract. Fortune Aza Technical pesticide containing 14% azadirachtin (extracted from neem seed/kernel source) was obtained from Fortune Biotech Ltd. of Secunderabad, India.
  • Solutions of neem oil limonoid extract and Fortune Aza Technical were prepared at 5 mg/mL in DMSO followed by ten-fold dilution in PDB to give a concentration of 0.5 mg/mL in 10% DMSO/90% PDB.
  • Stock solutions of 3-octenoic acid and trans-2-octenoic acid as Compound B for testing of individual MICs were prepared at 25 μL/mL by adding 25 μL of each Compound B to 975 μL DMSO followed by 10-fold dilution in PDB.
  • For testing in combination with neem oil limonoid extract and Fortune Aza Technical, stock solutions of 3-octenoic acid and trans-2-octenoic acid were prepared at 6.25 L/mL by adding 62.5 μL of the respective compound to 937.5 μL of DMSO followed by 10-fold dilution in PDB (ratio 11.7). Stock solutions of 3-octenoic acid and trans-2-octenoic acid were prepared at 3.125 L/mL for testing in combination by adding 31.25 μL of the respective compound to 968.75 μL of DMSO followed by 10-fold dilution in PDB (ratio 6.0 or 5.9). Stock solutions of 3-octenoic acid and trans-2-octenoic acid at 0.625 L/mL for testing in combination were prepared by adding 6.25 μL of the respective compound to 993.75 μL of DMSO followed by 10-fold dilution in PDB (ratio 1.2). The density of 3-octenoic acid was assumed to be 0.938 g/mL. The density of trans-2-octenoic acid was assumed to be 0.955 g/mL. Combinations were prepared by adding 0.5 mL of 6.25 μL/mL, 3.125 μL/mL, or 0.625 μL/mL 3-octenoic acid ortrans-2-octenoic acid, as prepared above (as Compound B), to 0.5 mL neem oil limonoid extract or Fortune Aza Technical at 0.5 mg/mL in acid DMSO/90% PDB (as Compound A) for testing in the synergistic growth inhibition assay. Each combination was observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Tables 5 and 6.
  • TABLE 5
    Growth inhibition of Botrytis cinerea by limonoid extract from cold-pressed
    neem oil in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Neem oil 0.25
    limonoid extract
    3-octenoic acid 0.14656
    Trans-2-octenoic acid 0.07461
    1 Neem oil 3-octenoic acid 0.0078125 0.09160 11.7 0.66
    limonoid extract
    2 Neem oil 3-octenoic acid 0.015625 0.09160 5.9 0.69
    limonoid extract
    3 Neem oil 3-octenoic acid 0.0625 0.07656 1.2 0.75
    limonoid extract
    4 Neem oil Trans-2-octenoic acid 0.0078125 0.04663 6.0 0.66
    limonoid extract
    5 Neem oil Trans-2-octenoic acid 0.03125 0.03730 1.2 0.63
    limonoid extract
  • TABLE 6
    Growth inhibition of Botrytis cinerea by Fortune Aza Technical
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Fortune Aza 0.25
    Tech.
    3-octenoic acid 0.14656
    Trans-2-octenoic acid 0.07461
    1 Fortune Aza 3-octenoic acid 0.0078125 0.09160 11.7 0.66
    Tech.
    2 Fortune Aza 3-octenoic acid 0.015625 0.09160 5.9 0.69
    Tech.
    3 Fortune Aza 3-octenoic acid 0.0625 0.07656 1.2 0.75
    Tech.
    4 Fortune Aza Trans-2-octenoic acid 0.0078125 0.04663 6.0 0.66
    Tech.
    5 Fortune Aza Trans-2-octenoic acid 0.03125 0.03730 1.2 0.63
    Tech.
    • Example 6: Growth Inhibition of Fusarium oxysporum by Fludioxonil in Combination with Various Exemplary Saturated Aliphatic Acids
  • Sample Preparation:
  • 20 mg fludioxonil was dissolved in 10 mL dimethylsulfoxide (DMSO) and the resulting solution was diluted 2-fold in DMSO to give a concentration of 1 mg/mL. This solution was diluted 10-fold in potato dextrose broth (PDB) to give a concentration of 0.1 mg/mL in 10% DMSO/90% PDB. The solubility of fludioxonil in 10% DMSO/90% PDB was determined to be 0.0154 mg/mL using high performance liquid chromatography. A solution of 0.000963 mg/mL fludioxonil was prepared by adding 625 μL of 0.0154 mg/mL fludioxonil to 9375 μL of PDB.
  • For testing individual MICs, stock solutions of hexanoic acid or octanoic acid as Component B were prepared by adding 100 μL hexanoic acid (93 mg) or octanoic acid (91 mg) to 900 μL PDB resulting in concentrations of 9.3 mg/mL and 9.1 mg/mL, respectively. A stock solution of decanoic acid was prepared at 10 mg/mL in DMSO followed by 10-fold dilution in PDB producing a concentration of 1 mg/mL in 10% DMSO/90% PDB. The stock solution of decanoic acid, potassium salt, was prepared by adding 100 mg to 10 mL of PDB resulting in a concentration of 10 mg/mL. A stock solution of dodecanoic acid was prepared at 1 mg/mL in DMSO followed by 10-fold dilution in PDB producing a concentration of 0.1 mg/mL in 10% DMSO/90% PDB.
  • For testing MICs of combinations, a solution of hexanoic acid at 0.29 mg/mL was prepared by adding 156 μL of the 9.3 mg/mL stock solution to 4844 μL PDB. Similarly, a solution of octanoic acid at 1.14 mg/mL was prepared diluting the 9.1 mg/mL stock solution in PDB. A solution of decanoic acid at 0.5 mg/mL was prepared by 2-fold dilution of the 1 mg/mL stock solution. A solution of decanoic acid, potassium salt, at 0.156 mg/mL was prepared by adding 78 μL of the 10 mg/mL stock solution to 4922 μL PDB. A solution of dodecanoic acid at 0.2 mg/mL was prepared by dissolving 2 mg in 1 mL DMSO followed by 10-fold dilution in PDB at 40° C.
  • Combinations for results shown in Table 7 were prepared by adding 0.5 mL of 0.0154 mg/mL fludioxonil to 0.5 mL of each of the stock solutions. Each combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Table 7.
  • TABLE 7
    Growth inhibition of Fusarium oxysporum by fludioxonil in combination
    with various exemplary saturated aliphatic acids (and salts thereof).
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Fludioxonil 4.8125 × 10−4
    Hexanoic acid 0.14531
    Octanoic acid 0.56875
    Decanoic acid 0.25
    Decanoic acid, 0.078125
    potassium salt
    Dodecanoic acid 0.1
    1 Fludioxonil Hexanoic acid 1.20375 × 10−4 0.00114 10 0.26
    2 Fludioxonil Octanoic acid 1.20375 × 10−4 0.00444 37 0.26
    3 Fludioxonil Decanoic acid 1.20375 × 10−4 0.00195 16 0.26
    4 Fludioxonil Decanoic acid, 1.20375 × 10−4 0.00061 5 0.26
    potassium salt
    5 Fludioxonil Dodecanoic acid 1.20375 × 10−4 0.00078 7 0.26
  • Combinations for results shown in Table 8 were prepared by adding 0.5 mL of 0.000963 mg/mL fludioxonil to 0.5 mL of each of the stock solutions.
  • TABLE 8
    Growth inhibition of Fusarium oxysporum by fludioxonil in
    combination with various exemplary saturated aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Fludioxonil 4.8125 × 10−4
    Hexanoic acid 0.29
    Octanoic acid 1.14
    Decanoic acid 0.25
    Decanoic acid, 0.078125
    potassium salt
    Dodecanoic acid 0.1
    1 Fludioxonil Hexanoic acid 1.20375 × 10−4 0.03633 309 0.38
    2 Fludioxonil Octanoic acid 1.20375 × 10−4 0.14219 1181 0.38
    3 Fludioxonil Decanoic acid 1.20375 × 10−4 0.0625 519 0.5
    4 Fludioxonil Decanoic acid, 1.20375 × 10−4 0.01953 162 0.5
    potassium salt
    5 Fludioxonil Dodecanoic acid 1.20375 × 10−4 0.025 208 0.5
    • Example 7: Growth Inhibition of Fusarium oxysporum by Limonoid Extract from Cold-Pressed Neem Oil and Fortune Aza Technical (Azadirachtin Extract) in Combination with Various Exemplary Saturated Aliphatic Acids
  • Sample Preparation:
  • An extract of limonoids was prepared from cold-pressed neem oil using solvent extraction with hexane and methanol to prepare a neem oil limonoid extract. Fortune Aza Technical pesticide containing 14% azadirachtin (extracted from neem seed/kernel source) was obtained from Fortune Biotech Ltd. of Secunderabad, India (also referred to as “Azatech”). Solutions of neem oil limonoid extract and Fortune Aza Technical were prepared at 5 mg/mL in DMSO followed by ten-fold dilution in PDB to give a concentration of 0.5 mg/mL in 10% DMSO/90% PDB. These solutions were used for testing the individual MICs.
  • For testing the individual MIC of octanoic acid, a solution was prepared by adding 100 uL octanoic acid (91 mg) to 900 uL PDB resulting in concentrations of 9.1 mg/mL. A stock solution of decanoic acid was prepared at 10 mg/mL in DMSO followed by 10-fold dilution in PDB producing a concentration of 1 mg/mL in 10% DMSO/90% PDB.
  • Combinations with octanoic acid were prepared by dissolving 5 mg neem oil limonoid extract or Fortune Aza Technical in 1 mL of DMSO and adding 6.25 uL octanoic acid (d=0.91 g/mL) followed by 10-fold dilution in PDB. This produced a solution containing 0.5 mg/mL neem oil limonoid extract or Fortune Aza Technical and 0.56875 mg/mL octanoic acid. Combinations with decanoic acid were prepared by dissolving 5 mg neem oil limonoid extract or Fortune Aza Technical in 1 mL of DMSO and adding 2.5 mg of decanoic acid followed by 10-fold dilution in PDB. This produced a solution containing 0.5 mg/mL neem oil limonoid extract or Fortune Aza Technical and 0.25 mg/mL decanoic acid.
  • Each combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following a 24 hour incubation period, and the FIC Index for each combination calculated, as shown below in Table 9.
  • TABLE 9
    Growth inhibition of Fusarium oxysporum by neem oil limonoid extract or Fortune Aza
    Technical (Azatech) in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Neem oil 0.5
    limonoid extract
    Azatech 0.5
    Octanoic acid 0.56875
    Decanoic acid 0.25
    1 Neem oil Octanoic acid 0.0625 0.07109 1.14 0.25
    limonoid extract
    2 Neem oil Decanoic acid 0.125 0.0625 0.5 0.5
    limonoid extract
    3 Fortune Octanoic acid 0.0625 0.07109 1.14 0.25
    Aza Tech.
    4 Fortune Decanoic acid 0.125 0.0625 0.5 0.5
    Aza Tech.
    • Sample Preparation for Examples 8-34
  • For each of experimental Examples 8-34 described below, concentrated stock solutions, and diluted working solutions were prepared for each of the exemplary pesticidal active ingredients as Component A, and each of the exemplary unsaturated and saturated aliphatic acids as Component B, in accordance with the following descriptions:
  • Compound A Pesticidal Active Ingredients:
  • Concentrated stock solutions were prepared by dissolving pesticidal active ingredient in 100% dimethylsulfoxide (DMSO), which were then diluted 10-fold in potato dextrose broth (PDB) to give a working stock solution, as described below:
  • Pyraclostrobin (available from Santa Cruz Biotech, Dallas, Tex., USA, as stock 4 SC-229020): A 0.5 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.05 mg/mL working stock solution, for which an effective solubilized concentration of 0.015 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.015 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Azoxystrobin (available from Sigma-Aldrich, St. Louis, Mo., USA, as stock #31697): A 1.75 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.175 mg/mL working stock solution, for which an effective solubilized concentration of 0.15 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.15 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Chlorothalonil (available from Chem Service Inc., West Chester, Pa., USA, as stock #N-11454): A 0.5 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.05 mg/mL working stock solution, for which an effective solubilized concentration of 0.002 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.002 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Fludioxonil (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China): A 1.05 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.105 mg/mL working stock solution, for which an effective solubilized concentration of 0.021 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.021 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Cyprodinil (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China): A 1.37 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.137 mg/mL working stock solution, for which an effective solubilized concentration of 0.009 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.009 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Metalaxyl: A 3.32 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.332 mg/mL working stock solution, for which an effective solubilized concentration of 0.316 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.316 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Difenoconazole (available from Santa Cruz Biotech, Dallas, Tex., USA, as stock no. SC-204721): A 1.3 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.13 mg/mL working stock solution, for which an effective solubilized concentration of 0.051 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.051 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Propiconazole (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China): A 1.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.10 mg/mL working stock solution, for which an effective solubilized concentration of 0.089 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.089 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Epoxiconazole (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China): A 2.5 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.25 mg/mL working stock solution, for which an effective solubilized concentration of 0.03 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.025 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Tebuconazole (available from Shanghai Terppon Chemical Co. Ltd., of Shanghai, China): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working stock solution, for which an effective solubilized concentration of 0.45 mg/mL was verified using high performance liquid chromatography (HPLC). This 0.45 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in Tables the tables below.
  • Picoxystrobin (available from Sigma Aldrich, #33658): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working picoxystrobin stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Isopyrazam (available from Sigma Aldrich, #32532): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working isopyrazam stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Penthiopyrad (available from aksci.com, #X5975): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working penthiopyrad stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Oxathiapiprolin (available from carbosynth.com, #FO159014): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working oxathiapiprolin stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Prothioconazole (available from Sigma Aldrich, #34232): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working prothioconazole stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Trifloxystrobin (available from Sigma Aldrich, #46447): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working trifloxystrobin stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Mancozeb (available from Sigma Aldrich, #45553): A 5.0 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a nominal 0.50 mg/mL working penthiopyrad stock solution, which was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Thyme oil (available from Sigma-Aldrich, St. Louis, Mo., USA as stock #W306509), garlic oil (available from New Directions Aromatics, Missisauga, ON, Canada), lemongrass oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OL123), wintergreen oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OW134), peppermint oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OP1531), spearmint oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #AS132), clove leaf oil (available from New Directions Aromatics, Missisauga, ON, Canada), cinnamon leaf oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OC2131), tea tree oil (available from Newco Natural Technology, Calgary, AB, Canada), geranium oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OW134), peppermint oil (available from Xenex Labs, Coquitlam, BC, Canada as stock #OG1042), rosemary oil (available from Xenex Labs of Coquitlam, BC, Canada as stock #OR131), and oregano oil (available from New Directions Aromatics, Missisauga, ON, Canada): A 100 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 10 mg/mL concentration. This 10 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below. Nootkatone(+) (available from Alfa Aesar, Ward Hill, Mass., USA as stock #A19166): A 10 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 1.0 mg/mL concentration. This 1.0 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in Tables 10-111 below.
  • Neem oil limonoid extract: An extract of limonoids was prepared from cold-pressed neem oil using solvent extraction with hexane and methanol to prepare a neem oil limonoid extract. A 5 mg/mL stock solution of neem oil limonoid extract in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 0.5 mg/mL concentration. This 0.5 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Fortune Aza Technical: Fortune Aza Technical™ pesticide containing 14% azadirachtin (extracted from neem seed/kernel source) was obtained from Fortune Biotech Ltd. of Secunderabad, India. A 5 mg/mL stock solution of Fortune Aza Technical in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 0.5 mg/mL concentration. This 0.5 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Karanja oil flavonoid extract: An extract of flavonoids was prepared from cold-pressed karanja oil by solvent extraction. A 5 mg/mL stock solution of karanja oil flavonoid extract in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 0.5 mg/mL concentration. This 0.5 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Salannin: Salannin was extracted and purified from cold-pressed neem oil by solvent extraction. A 1 mg/mL stock solution of salannin in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 0.1 mg/mL concentration. This 0.1 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Compound B Unsaturated Aliphatic Acids:
  • Concentrated stock solutions were prepared by dissolving each exemplary unsaturated aliphatic acid in 100% dimethylsulfoxide (DMSO), which were then diluted 10-fold in potato dextrose broth (PDB) to give a working stock solution, as described below:
  • Trans-2-hexenoic acid, trans-3-hexenoic acid, cis-3-hexenoic acid, 5-hexenoic acid, 3-heptenoic acid, trans-2-octenoic acid, trans-3-octenoic acid, 3-octenoic acid, 7-octenoic acid, 3-decenoic acid, cis-3-decenoic acid, 9-decenoic acid, trans-2-nonenoic acid, 3-nonenoic acid, (9Z)-octadecenoic acid (oleic acid) (all available from Sigma-Aldrich, St. Louis, Mo., USA), trans-2-decenoic acid (available from TCI America, Portland, Oreg., USA as stock #D0098), cis-2-decenoic acid (available from BOC Sciences, Sirley, N.Y., USA), and trans-2-undecenoic acid (available from Alfa Aesar, Ward Hill, Mass., USA as stock #L-11579): A 50 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 5 mg/mL concentration. This 5 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • (2E,4E)-2,4-hexadienoic acid (available from Sigma-Aldrich, St. Louis, Mo., USA): A 20 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 2 mg/mL concentration. This 2 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in the tables below.
  • Compound B Saturated Aliphatic Acids:
  • Concentrated stock solutions were prepared by dissolving each exemplary saturated aliphatic acid in 100% dimethylsulfoxide (DMSO), which were then diluted 10-fold in potato dextrose broth (PDB) to give a working stock solution, as described below:
  • Hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid (all available from Sigma-Aldrich, St. Louis, Mo., USA): A 50 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 5 mg/mL concentration. This 5 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in data Tables below.
  • Decenoic acid (available from Sigma-Aldrich, St. Louis, Mo., USA): A 10 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 1 mg/mL concentration. This 1 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in data Tables below.
  • Dodecenoic acid (available from Sigma-Aldrich, St. Louis, Mo., USA): A 1 mg/mL stock solution in 100% DMSO was diluted 10-fold in PDB to provide a working stock solution of 0.1 mg/mL concentration. This 0.1 mg/mL effective concentration working stock solution was used for further serial dilution in PDB to the required individual concentrations as specified in data Tables below.
  • Exemplary Hydroxy-substituted aliphatic acids: 2- and 3-hydroxybutyric acid, 2-hydroxyhexanoic acid, 12-hydroxydodecanoic acid (all available from Sigma-Aldrich, St. Louis, Mo., USA); 3-hydroxydecanoic acid, 3-hydroxyhexanoic acid (both available from Shanghai Terppon Chemical, Shanghai, China); 3-, 8-, 10-hydroxyoctanoic acid (all available from AA Blocks LLC, San Diego, Calif., USA), 2-hydroxyoctanoic acid (available from Alfa Aesar, Ward Hill, Mass., USA): a stock solution was prepared for each by dissolving each acid in 100% DMSO, which was then diluted in PDB to 10% DMSO concentration, before further serial dilution in PDB to the required individual concentrations as specified in the data Tables below.
  • Exemplary alkyl-substituted aliphatic acids: 2-ethylhexanoic acid, 2-methyloctanoic acid, 3-methylnonanoic acid, 3-methylbutyric acid (all available from Sigma-Aldrich, St. Louis, Mo., USA); 2,2-diethylbutyric acid, 2- and 4-methylhexanoic acid, 2-methyldecanoic acid (all available from AA Blocks LLC, San Diego, Calif., USA); 3-methylhexanoic acid (available from 1 ClickChemistry Inc., Kendall Park, N.J., USA): a stock solution was prepared for each by dissolving each acid in 100% DMSO, which was then diluted in PDB to 10% DMSO concentration, before further serial dilution in PDB to the required individual concentrations as specified in the data Tables below.
  • Exemplary amino-substituted aliphatic acid: 3-aminobutyric acid (available from AK Scientific Inc., Union City, Calif., USA): a stock solution was prepared by dissolving each acid in 100% DMSO, which was then diluted in PDB to 10% DMSO concentration, before further serial dilution in PDB to the required individual concentrations as specified in the data Tables below.
  • The working stock solutions for each Compound A and Compound B component were then serially diluted to test the individual MIC of each pesticidal active ingredient (as Compound A), each unsaturated or saturated aliphatic acid (as Compound B), and the combined MIC of each combination of Compound A and Compound B, according to the synergistic growth inhibition assay described above.
    • Example 8: Growth Inhibition of Fusarium oxysporum by Pyraclostrobin, Azoxystrobin, Chlorothalonil, Fluidioxonil, Cyprodinil, Difenoconazole, and Tebuconazole, in Combination with Various Exemplary Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, chlorothalonil, fluidioxonil, cyprodinil, difenoconazole, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 10-15 below. Working solutions of hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, and decanoic acid, (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 10-15 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 48 hours, and the FIC Index for each combination calculated, as shown in Tables 10-15 below.
  • TABLE 10
    Growth inhibition of Fusarium oxysporum by pyraclostrobin,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.015
    Hexanoic acid 0.15625
    Heptanoic acid 0.15625
    Octanoic acid 0.15625
    Nonanoic acid 0.15625
    Decanoic acid 0.125
    Dodecanoic acid 0.1
    3-Hydroxybutyric acid 10
    3-Hydroxydecanoic acid 0.25
    1 Pyraclostrobin Hexanoic acid 0.00187 0.019531 10 0.25
    2 Pyraclostrobin Heptanoic acid 0.00375 0.039062 10 0.50
    3 Pyraclostrobin Octanoic acid 0.00187 0.039062 21 0.38
    4 Pyraclostrobin Nonanoic acid 0.00375 0.039062 10 0.50
    5 Pyraclostrobin Decanoic acid 0.00375 0.015625 4 0.38
    6 Pyraclostrobin Dodecanoic acid 0.00375 0.025 7 0.50
    7 Pyraclostrobin 3-Hydroxybutyric acid 0.00375 2.5 667 0.50
    8 Pyraclostrobin 3-Hydroxydecanoic acid 0.00187 0.015625 8 0.25
  • TABLE 11
    Growth inhibition of Fusarium oxysporum by azoxystrobin, in
    combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Azoxystrobin 0.075
    Hexanoic acid 0.15625
    Heptanoic acid 0.15625
    Octanoic acid 0.15625
    Nonanoic acid 0.07812
    Dodecanoic acid 0.1
    1 Azoxystrobin Hexanoic acid 0.01875 0.039062 2 0.50
    2 Azoxystrobin Heptanoic acid 0.01875 0.039062 2 0.50
    3 Azoxystrobin Octanoic acid 0.01875 0.039062 2 0.50
    4 Azoxystrobin Nonanoic acid 0.01875 0.019531 1 0.50
    5 Azoxystrobin Dodecanoic acid 0.01875 0.025 1.3 0.50
  • TABLE 12
    Growth inhibition of Fusarium oxysporum by chlorothalonil,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Chlorothalonil 0.000125
    Heptanoic acid 0.15625
    Octanoic acid 0.3125
    Nonanoic acid 0.3125
    Dodecanoic acid 0.1
    3-Hydroxydecanoic 0.25
    acid
    1 Chlorothalonil Heptanoic acid 6.25 × 10−5 0.039062 625 0.75
    2 Chlorothalonil Octanoic acid 6.25 × 10−5 0.039062 625 0.63
    3 Chlorothalonil Nonanoic acid 6.25 × 10−5 0.019531 313 0.56
    4 Chlorothalonil Dodecanoic acid 6.25 × 10−5 0.025 400 0.75
    5 Chlorothalonil 3-Hydroxydecanoic 1.9531 × 10−6   0.003125 16000 0.19
    acid
  • TABLE 13
    Growth inhibition of Fusarium oxysporum by fludioxonil and cyprodinil,
    in combination with an exemplary saturated aliphatic acid
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Fludioxonil 0.021
    Cyprodinil 0.009
    Dodecanoic acid 0.1
    3-Hydroxydecanoic acid 0.25
    1 Fludioxonil Dodecanoic acid 0.00525 0.025 5 0.50
    2 Fludioxonil 3-Hydroxydecanoic acid 0.00131 0.03125 24 0.19
    3 Cyprodinil 3-Hydroxydecanoic acid 0.00225 0.03125 14 0.50
  • TABLE 14
    Growth inhibition of Fusarium oxysporum by difenoconazole,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Difenoconazole 0.051
    Heptanoic acid 0.15625
    Octanoic acid 0.3125
    1 Difenoconazole Heptanoic acid 0.01275 0.039062 3 0.50
    2 Difenoconazole Octanoic acid 0.01275 0.078125 6 0.50
  • TABLE 15A
    Growth inhibition of Fusarium oxysporum by tebuconazole, in
    combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Tebuconazole 0.255
    Heptanoic acid 0.15625
    Octanoic acid 0.15625
    Nonanoic acid 0.15625
    Decanoic acid 0.03125
    Dodecanoic acid 0.1
    1 Tebuconazole Heptanoic acid 0.05625 0.039062 0.7 0.50
    2 Tebuconazole Octanoic acid 0.05625 0.039062 0.7 0.50
    3 Tebuconazole Nonanoic acid 0.05625 0.039062 0.7 0.50
    4 Tebuconazole Decanoic acid 0.05625 0.007812 0.14 0.50
    5 Tebuconazole Dodecanoic acid 0.05625 0.0025 0.4 0.50
  • TABLE 15B
    Growth inhibition of Fusarium oxysporum by various synthetic fungicides
    in combination with saturated 3-hydroxy aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.015
    Azoxystrobin 0.15
    Fludioxonil 0.021
    Difenoconazole 0.051
    Tebuconazole 0.225
    3-Hydroxybuturic acid 10
    3-Hydroxyhexanoic acid 2.5
    3-Hydroxydecanoic acid 0.25
    1 Pyraclostrobin 3-Hydroxybuturic acid 0.001875 2.5 1333 0.38
    2 Azoxystrobin 3-Hydroxybuturic acid 0.0375 2.5 67 0.50
    3 Azoxystrobin 3-Hydroxyhexanoic acid 0.0375 0.625 17 0.50
    4 Fludioxonil 3-Hydroxybuturic acid 0.00525 2.5 476 0.50
    5 Difenoconazole 3-Hydroxybuturic acid 0.01275 2.5 196 0.50
    6 Tebuconazole 3-Hydroxybuturic acid 0.05625 2.5 44 0.50
    7 Tebuconazole 3-Hydroxydecanoic acid 0.05625 0.0625 1.1 0.50
    • Example 9: Growth Inhibition of Sclerotinta Sclerotiorum by Pyraclostrobin, Azoxystrobin, Propiconazole, Epiconazole, Tebuconazole, and Difenoconazole, in Combination with Various Exemplary Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, propiconazole, epiconazole, tebuconazole, and difenoconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 16-20 below. Working solutions of hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, and dodecanoic acid, (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 16-20 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 7 days, and the FIC Index for each combination calculated, as shown in Tables 16-20 below.
  • TABLE 16
    Growth inhibition of Sclerotinia sclerotiorum by pyraclostrobin,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0075
    Hexanoic acid 0.039062
    Heptanoic acid 0.039062
    Octanoic acid 0.019531
    Nonanoic acid 0.019531
    Decanoic acid 0.15625
    Dodecanoic acid 0.05
    1 Pyraclostrobin Hexanoic acid 9.375 × 10−4 0.009765 10 0.38
    2 Pyraclostrobin Heptanoic acid 4.688 × 10−4 0.004883 10 0.19
    3 Pyraclostrobin Octanoic acid 9.375 × 10−4 0.004883 5 0.38
    4 Pyraclostrobin Nonanoic acid 4.688 × 10−4 0.004883 10 0.31
    5 Pyraclostrobin Decanoic acid 9.375 × 10−4 0.001953 2 0.14
    6 Pyraclostrobin Dodecanoic acid 9.375 × 10−4 0.00625 7 0.25
  • TABLE 17
    Growth inhibition of Sclerotinia sclerotiorum by azoxystrobin,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Azoxystrobin 0.15
    Hexanoic acid 0.039062
    Heptanoic acid 0.039062
    Octanoic acid 0.039062
    Nonanoic acid 0.078125
    Decanoic acid 0.078125
    Dodecanoic acid 0.05
    1 Azoxystrobin Hexanoic acid 0.0375 0.019531 0.52 0.75
    2 Azoxystrobin Heptanoic acid 0.0375 0.009766 0.26 0.50
    3 Azoxystrobin Octanoic acid 0.01875 0.004883 0.26 0.25
    4 Azoxystrobin Nonanoic acid 0.01875 0.004883 0.26 0.19
    5 Azoxystrobin Decanoic acid 0.0375 0.003906 0.10 0.75
    6 Azoxystrobin Dodecanoic acid 0.009375 0.003125 0.33 0.13
  • TABLE 18
    Growth inhibition of Sclerotinia sclerotiorum by propiconazole,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Propiconazole 0.089
    Decanoic acid 0.078125
    Dodecanoic acid 0.05
    1 Propiconazole Decanoic acid 0.0445 0.0078125 0.18 0.60
    2 Propiconazole Dodecanoic acid 0.0223 0.0125 0.56 0.50
  • TABLE 19
    Growth inhibition of Sclerotinia sclerotiorum by epiconzaole and tebuconazole,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Epoxiconazole 0.03
    Tebuconazole 0.225
    Hexanoic acid 0.078125
    Heptanoic acid 0.0390625
    Octanoic acid 0.078125
    Nonanoic acid 0.078125
    Decanoic acid 0.03125
    Dodecanoic acid 0.1
    1 Epoxiconazole Heptanoic acid 0.0075 0.009765 1.3 0.50
    2 Epoxiconazole Octanoic acid 0.00375 0.004883 1.3 0.19
    3 Epoxiconazole Decanoic acid 0.0075 0.003906 0.5 0.38
    4 Epoxiconazole Dodecanoic acid 0.00375 0.00625 1.7 0.19
    5 Tebuconazole Hexanoic acid 0.028125 0.009765 0.35 0.25
    6 Tebuconazole Heptanoic acid 0.028125 0.004883 0.17 0.25
    7 Tebuconazole Octanoic acid 0.0028125 0.004883 0.17 0.19
    8 Tebuconazole Nonanoic acid 0.028125 0.004883 0.17 0.19
    9 Tebuconazole Decanoic acid 0.05625 0.003906 0.07 0.38
    10 Tebuconazole Dodecanoic acid 0.028125 0.00625 0.22 0.19
  • TABLE 20A
    Growth inhibition of Sclerotinia sclerotiorum by difenoconazole,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Difenoconazole 0.01275
    Nonanoic acid 0.039062
    Decanoic acid 0.015615
    Dodecanoic acid 0.025
    1 Difenoconazole Nonanoic acid 0.006375 0.009766 1.5 0.75
    2 Difenoconazole Decanoic acid 0.006375 0.003906 0.6 0.75
    4 Difenoconazole Dodecanoic acid 0.003188 0.00625 2.0 0.50
  • TABLE 20B
    Growth inhibition of Sclerotinia sclerotiorum by various fungicides,
    in combination with various exemplary saturated hydroxy aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.00375
    Azoxyst robin 0.075
    Chlorothalonil 3.125 × 10−5
    Cyprodinil 0.009
    Metalaxyl 1.261
    Difenoconazole 0.0255
    Propiconazole 0.089
    Epoxiconazole 0.03
    Tebuconazole 0.05625
    3-Hydroxybuturic acid 5.0
    3-Hydroxyhexanoic acid 2.5
    3-Hydroxydecanoic acid 0.0625
    1 Pyraclostrobin 3-Hydroxybuturic acid 0.0009375 1.25 1333 0.50
    2 Pyraclostrobin 3-Hydroxyhexanoic acid 0.0009375 0.625 667 0.50
    3 Pyraclostrobin 3-Hydroxydecanoic acid 0.0009375 0.015625 17 0.50
    4 Azoxystrobin 3-Hydroxyhexanoic acid 0.01875 0.625 33 0.50
    5 Chlorothalonil 3-Hydroxyhexanoic acid 7.813 × 10−6 1.25 160000 0.75
    6 Cyprodinil 3-Hydroxyhexanoic acid 0.00225 1.25 556 0.75
    7 Metalaxyl 3-Hydroxyhexanoic acid 0.31525 1.25 4 0.75
    8 Difenoconazole 3-Hydroxybuturic acid 0.006375 2.5 392 0.75
    9 Difenoconazole 3-Hydroxyhexanoic acid 0.006375 1.25 196 0.75
    10 Propiconazole 3-Hydroxybuturic acid 0.02225 2.5 112 0.75
    11 Propiconazole 3-Hydroxyhexanoic acid 0.02225 1.25 56 0.75
    12 Epoxiconazole 3-Hydroxybuturic acid 0.001875 0.625 333 0.19
    13 Epoxiconazole 3-Hydroxyhexanoic acid 0.00375 0.625 167 0.38
    14 Tebuconazole 3-Hydroxybuturic acid 0.014062 1.25 89 0.50
    15 Tebuconazole 3-Hydroxyhexanoic acid 0.014062 0.625 44 0.50
    • Example 10: Growth Inhibition of Botrytis cinerea by Pyraclostrobin, Azoxystrobin, Cyprodinil, Metalaxyl, Epiconazole, Tebuconazole, Propiconazole, and Difenoconazole, in Combination with Various Exemplary Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, cyprodiil, metalaxyl, epiconazole, tebuconazole, propiconazole, and difenoconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 21-26 below. Working solutions of hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, and dodecanoic acid, (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 21-26 below. Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 48 hours, and the FIC Index for each combination calculated, as shown in Tables 21-26 below.
  • TABLE 21
    Growth inhibition of Botrytis cinerea by pyraclostrobin, in
    combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0019
    Hexanoic acid 0.078125
    Heptanoic acid 0.078125
    Octanoic acid 0.078125
    Nonanoic acid 0.078125
    Decanoic acid 0.03125
    Dodecanoic acid 0.025
    1 Pyraclostrobin Hexanoic acid 9.375 × 10−4 0.009766 10 0.63
    2 Pyraclostrobin Heptanoic acid 9.375 × 10−4 0.004883 5 0.56
    3 Pyraclostrobin Octanoic acid 4.688 × 10−4 0.002441 5 0.28
    4 Pyraclostrobin Nonanoic acid 4.688 × 10−4 0.002441 5 0.28
    5 Pyraclostrobin Decanoic acid 2.344 × 10−4 0.001953 8 0.19
    6 Pyraclostrobin Dodecanoic acid 9.375 × 10−4 0.003125 3 0.63
  • TABLE 22
    Growth inhibition of Botrytis cinerea by azoxystrobin, in
    combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Azoxystrobin 0.0375
    Hexanoic acid 0.078125
    Heptanoic acid 0.078125
    Octanoic acid 0.078125
    Nonanoic acid 0.078125
    Decanoic acid 0.078125
    1 Azoxystrobin Hexanoic acid 0.01875 0.019531 1 0.75
    2 Azoxystrobin Heptanoic acid 0.01875 0.009765 0.5 0.63
    3 Azoxystrobin Octanoic acid 0.01875 0.009765 0.5 0.63
    4 Azoxystrobin Nonanoic acid 0.01875 0.009765 0.5 0.63
    5 Azoxystrobin Decanoic acid 0.009375 0.078125 0.8 0.35
  • TABLE 23
    Growth inhibition of Botrytis cinerea by pyraclostrobin, cyprodinil,
    metalaxyl, azoxystrobin, epoxiconazole, and tebuconazole, in combination
    with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.00375
    Cyprodinil 0.0045
    Metalaxyl 0.316
    Azoxystrobin 0.075
    Epoxiconazole 0.03
    Tebuconazole 0.1125
    Decanoic acid 0.03125
    1 Pyraclostrobin Decanoic acid 2.344 × 10−4 0.001953 8 0.13
    3 Cyprodinil Decanoic acid 5.625 × 10−4 0.03125 28 0.63
    4 Metalaxyl Decanoic acid 0.0395 0.015625 0.4 0.63
    5 Azoxystrobin Decanoic acid 0.009375 0.0078125 0.8 0.38
    6 Epoxiconazole Decanoic acid 0.00375 0.015625 4 0.63
    7 Tebuconazole Decanoic acid 0.014062 0.0078125 0.6 0.38
  • TABLE 24
    Growth inhibition of Botrytis cinerea by difenoconazole and propiconazole,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Difenoconazole 0.051
    Propiconazole 0.089
    Hexanoic acid 0.15625
    Heptanoic acid 0.15625
    Octanoic acid 0.15625
    Nonanoic acid 0.15625
    Decanoic acid 0.3125
    Dodecanoic acid 0.05
    1 Difenoconazole Hexanoic acid 0.01275 0.039062 3.1 0.50
    2 Difenoconazole Heptanoic acid 0.01275 0.019531 1.5 0.38
    3 Difenoconazole Octanoic acid 0.01275 0.019531 1.5 0.38
    4 Difenoconazole Nonanoic acid 0.01275 0.019531 1.5 0.38
    5 Difenoconazole Decanoic acid 0.006275 0.015625 2.5 0.18
    6 Difenoconazole Dodecanoic acid 0.01275 0.0125 1.0 0.50
    7 Propiconazole Decanoic acid 0.011125 0.015625 1.4 0.18
    8 Propiconazole Dodecanoic acid 0.02225 0.0125 0.6 0.50
  • TABLE 25
    Growth inhibition of Botrytis cinerea by tebuconazole, in
    combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Tebuconazole 0.1125
    Hexanoic acid 0.078125
    Heptanoic acid 0.078125
    Octanoic acid 0.078125
    Nonanoic acid 0.078125
    Decanoic acid 0.015625
    Dodecanoic acid 0.05
    1 Tebuconazole Hexanoic acid 0.014062 0.009766 0.7 0.25
    2 Tebuconazole Heptanoic acid 0.014062 0.004883 0.3 0.19
    3 Tebuconazole Octanoic acid 0.014062 0.004883 0.3 0.19
    4 Tebuconazole Nonanoic acid 0.014062 0.004883 0.3 0.19
    5 Tebuconazole Decanoic acid 0.007031 0.003906 0.6 0.31
    6 Tebuconazole Dodecanoic acid 0.014062 0.003125 0.2 0.19
  • TABLE 26
    Growth inhibition of Botrytis cinerea by cyprodinil and metalaxyl,
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Cyprodinil 0.0045
    Metalaxyl 0.316
    Octanoic acid 0.078125
    Decanoic acid 0.078125
    Dodecanoic acid 0.05
    1 Cyprodinil Decanoic acid 0.001125 0.03125 28 0.65
    2 Metalaxyl Octanoic acid 0.01975 0.004883 0.25 0.13
    3 Metalaxyl Decanoic acid 0.0395 0.015625 0.4 0.33
    4 Metalaxyl Dodecanoic acid 0.079 0.0125 0.16 0.50
    • Example 11: Growth Inhibition of Fusarium oxysporum by Pyraclostrobin, Azoxystrobin, Fludioxonil, Cyprodinil, Difenoconazole, Epoxiconazole, and Tebuconazole, in Combination with Various Exemplary Unsaturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, fludioxonil, cyprodinil, difenoconazole, epoxiconazole, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 27-32 below. Working solutions of (2E,4E)-2,4-hexadienoic acid, trans-3-hexenoic acid, 4-hexenoic acid, 5-hexenoic acid, 3-heptenoic acid, trans-2-octenoic acid, trans-3-octenoic acid, 7-octenoic acid, 3-decenoic acid, 9-decenoic acid, trans-2-nonenoic acid, 3-nonenoic acid, trans-2-decenoic acid, and trans-2-undecenoic acid, (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 27-32 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 48 hours, and the FIC Index for each combination calculated, as shown in Tables 27-32 below.
  • TABLE 27
    Growth inhibition of Fusarium oxysporum by pyraclostrobin, in
    combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.015
    (2E,4E)-2,4-hexadienoic 0.025
    acid
    Trans-3-hexenoic acid 0.3125
    4-Hexenoic acid 0.3125
    5-Hexenoic acid 0.3125
    3-Heptenoic acid 0.15625
    Trans-2-octenoic acid 0.3125
    Trans-3-octenoic acid 0.15625
    7-Octenoic acid 0.3125
    3-Decenoic acid 0.3125
    9-Decenoic acid 0.3125
    1 Pyraclostrobin (2E,4E)-2,4-hexadienoic 0.00375 0.0625 17 0.50
    acid
    2 Pyraclostrobin Trans-3-hexenoic acid 0.001875 0.078125 42 0.38
    3 Pyraclostrobin 4-Hexenoic acid 0.00375 0.15625 42 0.75
    4 Pyraclostrobin 5-Hexenoic acid 0.00375 0.039062 10 0.38
    5 Pyraclostrobin 3-Heptenoic acid 0.001875 0.078125 42 0.63
    6 Pyraclostrobin Trans-2-octenoic acid 0.001875 0.019531 10 0.19
    7 Pyraclostrobin Trans-3-octenoic acid 0.001875 0.019531 10 0.25
    8 Pyraclostrobin 7-Octenoic acid 0.001875 0.019531 10 0.19
    9 Pyraclostrobin 3-Decenoic acid 0.00375 0.078125 21 0.50
    10 Pyraclostrobin 9-Decenoic acid 0.00375 0.039062 10 0.38
  • TABLE 28
    Growth inhibition of Fusarium oxysporum by azoxystrobin, in
    combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Azoxystrobin 0.15
    Trans-3-hexenoic acid 0.3125
    3-Heptenoic acid 0.15625
    Trans-2-nonenoic acid 0.15625
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.3125
    1 Azoxystrobin Trans-3-hexenoic acid 0.0375 0.078125 2 0.50
    2 Azoxystrobin 3-Heptenoic acid 0.001875 0.019531 1 0.25
    3 Azoxystrobin Trans-2-nonenoic acid 0.0375 0.039062 1 0.50
    4 Azoxystrobin 3-Decenoic acid 0.001875 0.019531 1 0.38
    5 Azoxystrobin 9-Decenoic acid 0.00375 0.039062 1 0.50
  • TABLE 29
    Growth inhibition of Fusarium oxysporum by fludioxonil and cyprodinil,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Fludioxonil 0.021
    Cyprodinil 0.009
    3-Heptenoic acid 0.15625
    3-Decenoic acid 0.15625
    1 Fludioxonil 3-Heptenoic acid 0.00525 0.03906 7 0.50
    2 Fludioxonil 3-Decenoic acid 0.00525 0.03906 7 0.50
    3 Cyprodinil 3-Decenoic acid 0.00225 0.019531 9 0.38
  • TABLE 30
    Growth inhibition of Fusarium oxysporum by difenoconazole, in
    combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Difenoconazole 0.051
    Trans-3-hexenoic acid 0.3125
    4-Hexenoic acid 0.3125
    3-Heptenoic acid 0.15625
    Trans-2-octenoic acid 0.15625
    3-Octenoic acid 0.15625
    Trans-3-octenoic acid 0.15625
    7-Octenoic acid 0.3125
    Trans-2-nonenoic acid 0.3125
    Trans-2-decenoic acid 0.078125
    9-Decenoic acid 0.15625
    1 Difenoconazole Trans-3-hexenoic acid 0.006375 0.078125 12 0.38
    2 Difenoconazole 4-Hexenoic acid 0.01275 0.15625 12 0.75
    3 Difenoconazole 3-Heptenoic acid 0.006375 0.078125 12 0.63
    4 Difenoconazole Trans-2-octenoic acid 0.01275 0.039062 3 0.50
    5 Difenoconazole 3-Octenoic acid 0.01275 0.019531 1.5 0.38
    6 Difenoconazole Trans-3-octenoic acid 0.01275 0.039062 3 0.50
    7 Difenoconazole 7-Octenoic acid 0.01275 0.039062 3 0.50
    8 Difenoconazole Trans-2-nonenoic acid 0.01275 0.039062 3 0.38
    9 Difenoconazole Trans-2-decenoic acid 0.01275 0.019531 1.5 0.50
    10 Difenoconazole 9-Decenoic acid 0.01275 0.039062 3 0.50
  • TABLE 31
    Growth inhibition of Fusarium oxysporum by epoxiconazole, in
    combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Epoxiconazole 0.03
    Trans-3-hexenoic acid 0.15625
    3-Heptenoic acid 0.15625
    Trans-2-octenoic acid 0.15625
    3-Octenoic acid 0.15625
    3-Decenoic acid 0.078125
    1 Epoxiconazole Trans-3-hexenoic acid 0.0075 0.078125 10 0.75
    2 Epoxiconazole 3-Heptenoic acid 0.0075 0.039062 5 0.50
    3 Epoxiconazole Trans-2-octenoic acid 0.0075 0.039062 5 0.50
    4 Epoxiconazole 3-Octenoic acid 0.0075 0.039062 5 0.50
    5 Epoxiconazole 3-Decenoic acid 0.0075 0.039062 5 0.75
  • TABLE 32
    Growth inhibition of Fusarium oxysporum by tebuconazole, in
    combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Tebuconazole 0.225
    Trans-2-octenoic acid 0.3125
    3-Octenoic acid 0.15625
    Trans-3-octenoic acid 0.15625
    7-Octenoic acid 0.15625
    Trans-2-nonenoic acid 0.3125
    3-Nonenoic acid 0.15625
    Trans-2-decenoic acid 0.15625
    9-Decenoic acid 0.078125
    Trans-2-undecenoic acid 0.15625
    1 Tebuconazole Trans-2-octenoic acid 0.05625 0.039062 0.7 0.38
    2 Tebuconazole 3-Octenoic acid 0.05625 0.019531 0.3 0.38
    3 Tebuconazole Trans-3-octenoic acid 0.05625 0.039062 0.7 0.50
    4 Tebuconazole 7-Octenoic acid 0.05625 0.039062 0.7 0.50
    5 Tebuconazole Trans-2-nonenoic acid 0.028125 0.019531 0.7 0.19
    6 Tebuconazole 3-Nonenoic acid 0.05625 0.019531 0.3 0.38
    7 Tebuconazole Trans-2-decenoic acid 0.05625 0.019531 0.3 0.38
    8 Tebuconazole 9-Decenoic acid 0.05625 0.039062 0.7 0.75
    9 Tebuconazole Trans-2-undecenoic acid 0.05625 0.019531 0.3 0.38
    • Example 12: Growth Inhibition of Sclerotinia sclerotiorum by Pyraclostrobin, Azoxystrobin, Chlorothalonil, Fludioxonil, Difenoconazole, Propiconazole, Epoxiconazole, and Tebuconazole, in Combination with Various Exemplary Unsaturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, chlorothalonil, fludioxonil, difenoconazole, propiconazole, epoxiconazole, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 33-42 below. Working solutions of (2E,4E)-2,4-hexadienoic acid, trans-2-hexenoic acid, trans-3-hexenoic acid, 5-hexenoic acid, 3-heptenoic acid, trans-2-octenoic acid, trans-3-octenoic acid, 3-octenoic acid, 7-octenoic acid, 3-decenoic acid, cis-3-hexenoic acid, 9-decenoic acid, trans-2-nonenoic acid, 3-nonenoic acid, (9Z)-octadecenoic acid, trans-2-decenoic acid, cis-2-decenoic acid, and trans-2-undecenoic acid (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 33-42 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 7 days, and the FIC Index for each combination calculated, as shown in Tables 33-42 below.
  • TABLE 33
    Growth inhibition of Sclerotinia sclerotiorum by pyraclostrobin,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0075
    (2E,4E)-2,4-hexadienoic acid 0.125
    Trans-2-hexenoic acid 0.15625
    Trans-3-hexenoic acid 0.15625
    5-Hexenoic acid 0.15625
    3-Heptenoic acid 0.078125
    Trans-2-octenoic acid 0.039062
    3-Octenoic acid 0.078125
    Trans-3-octenoic acid 0.039062
    7-Octenoic acid 0.039062
    Trans-2-nonenoic acid 0.019531
    3-Nonenoic acid 0.019531
    Trans-2-decenoic acid 0.019531
    3-Decenoic acid 0.039062
    9-Decenoic acid 0.039062
    Trans-2-undecenoic acid 0.019531
    (9Z)-octadecenoic acid 5.0
    1 Pyraclostrobin (2E,4E)-2,4-hexadienoic acid 0.001875 0.015625 8 0.38
    2 Pyraclostrobin Trans-2-hexenoic acid 0.000937 0.009765 10 0.19
    3 Pyraclostrobin Trans-3-hexenoic acid 0.000937 0.019531 21 0.25
    4 Pyraclostrobin 5-Hexenoic acid 0.000937 0.019531 21 0.25
    5 Pyraclostrobin 3-Heptenoic acid 0.000937 0.009766 10 0.25
    6 Pyraclostrobin Trans-2-octenoic acid 0.000469 0.004882 10 0.19
    7 Pyraclostrobin 3-Octenoic acid 0.000469 0.004882 10 0.13
    8 Pyraclostrobin Trans-3-octenoic acid 0.000469 0.004882 10 0.19
    9 Pyraclostrobin 7-Octenoic acid 0.000469 0.004882 10 0.19
    10 Pyraclostrobin Trans-2-nonenoic acid 0.000469 0.004882 10 0.31
    11 Pyraclostrobin 3-Nonenoic acid 0.000469 0.004882 10 0.31
    12 Pyraclostrobin Trans-2-decenoic acid 0.000937 0.002441 3 0.25
    13 Pyraclostrobin 3-Decenoic acid 0.000234 0.002441 10 0.09
    14 Pyraclostrobin 9-Decenoic acid 0.000469 0.004882 10 0.19
    15 Pyraclostrobin Trans-2-undecenoic acid 0.000469 0.004882 10 0.31
    16 Pyraclostrobin (9Z)-octadecenoic acid 0.00375 2.5 667 1.00
  • TABLE 34
    Growth inhibition of Sclerotinia sclerotiorum by pyraclostrobin,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.00375
    Trans-3-hexenoic acid 0.15625
    Cis-3-hexenoic acid 0.15625
    Trans-2-decenoic acid 0.019531
    Cis-2-decenoic acid 0.019531
    1 Pyraclostrobin Trans-3-hexenoic acid 0.001875 0.039062 21 0.75
    2 Pyraclostrobin Cis-3-hexenoic acid 0.001875 0.039062 21 0.75
    3 Pyraclostrobin Trans-2-decenoic acid 0.0009375 0.002441 3 0.38
    4 Pyraclostrobin Cis-2-decenoic acid 0.0009375 0.002441 3 0.38
  • TABLE 35
    Growth inhibition of Sclerotinia sclerotiorum by azoxystrobin,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Azoxystrobin 0.15
    Trans-3-hexenoic acid 0.15625
    5-Hexenoic acid 0.15625
    3-Heptenoic acid 0.078125
    3-Octenoic acid 0.039062
    Trans-3-octenoic acid 0.039062
    3-Nonenoic acid 0.039062
    Trans-2-decenoic acid 0.009766
    3-Decenoic acid 0.039062
    9-Decenoic acid 0.039062
    1 Azoxystrobin Trans-3-hexenoic acid 0.0375 0.039062 1 0.50
    2 Azoxystrobin 5-Hexenoic acid 0.0375 0.039062 1 0.50
    3 Azoxystrobin 3-Heptenoic acid 0.0375 0.019531 0.5 0.50
    4 Azoxystrobin 3-Octenoic acid 0.0375 0.019531 0.5 0.75
    5 Azoxystrobin Trans-3-octenoic acid 0.01875 0.009766 0.5 0.38
    6 Azoxystrobin 3-Nonenoic acid 0.0375 0.019531 0.5 0.75
    7 Azoxystrobin Trans-2-decenoic acid 0.0375 0.004882 0.1 0.75
    8 Azoxystrobin 3-Decenoic acid 0.01875 0.009766 0.5 0.38
    9 Azoxystrobin 9-Decenoic acid 0.01875 0.009766 0.5 0.38
  • TABLE 36
    Growth inhibition of Sclerotinia sclerotiorum by chlorothalonil,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Chlorothalonil 3.125 × 10−5
    Trans-2-nonenoic acid 0.039062
    3-Nonenoic acid 0.039062
    9-Decenoic acid 0.039062
    1 Chlorothalonil Trans-2-nonenoic acid 3.906 × 10−6 0.009766 2500 0.38
    2 Chlorothalonil 3-Nonenoic acid 7.813 × 10−6 0.019531 2500 0.75
    3 Chlorothalonil 9-Decenoic acid 7.813 × 10−6 0.019531 2500 0.75
  • TABLE 37
    Growth inhibition of Sclerotinia sclerotiorum by fludioxonil,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Fludioxonil 0.000164
    Trans-2-octenoic acid 0.078125
    3-Octenoic acid 0.078125
    Trans-2-nonenoic acid 0.078125
    3-Nonenoic acid 0.078125
    Trans-2-decenoic acid 0.039062
    9-Decenoic acid 0.15625
    1 Fludioxonil Trans-2-octenoic acid 8.203 × 10−5 0.019531 238 0.75
    2 Fludioxonil 3-Octenoic acid 8.203 × 10−5 0.019531 238 0.75
    3 Fludioxonil Trans-2-nonenoic acid 8.203 × 10−5 0.009766 119 0.63
    4 Fludioxonil 3-Nonenoic acid 8.203 × 10−5 0.009766 119 0.63
    5 Fludioxonil Trans-2-decenoic acid 8.203 × 10−5 0.009766 119 0.75
    6 Fludioxonil 9-Decenoic acid 8.203 × 10−5 0.019531 238 0.63
  • TABLE 38
    Growth inhibition of Sclerotinia sclerotiorum by difenoconazole,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Difenoconazole 0.0255
    Trans-2-octenoic acid 0.078125
    Trans-2-nonenoic acid 0.039062
    3-Nonenoic acid 0.078125
    Trans-2-decenoic acid 0.019531
    3-decenoic acid 0.039062
    9-Decenoic acid 0.078125
    Trans-2-undecenoic acid 0.039062
    1 Difenoconazole Trans-2-octenoic acid 0.006375 0.019531 3.1 0.50
    2 Difenoconazole Trans-2-nonenoic acid 0.006375 0.009766 1.5 0.50
    3 Difenoconazole 3-Nonenoic acid 0.006375 0.009766 1.5 0.38
    4 Difenoconazole Trans-2-decenoic acid 0.006375 0.009766 1.5 0.75
    5 Difenoconazole 3-Decenoic acid 0.006375 0.019531 3.1 0.75
    6 Difenoconazole 9-Decenoic acid 0.006375 0.019531 3.1 0.50
    7 Difenoconazole Trans-2-undecenoic acid 0.006375 0.009766 1.5 0.50
  • TABLE 39
    Growth inhibition of Sclerotinia sclerotiorum by propiconazole,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Propiconazole 0.089
    3-Heptenoic acid 0.078125
    Trans-2-nonenoic acid 0.019531
    Trans-2-decenoic acid 0.019531
    9-Decenoic acid 0.039062
    Trans-2-undecenoic acid 0.039062
    1 Propiconazole 3-Heptenoic acid 0.02225 0.019531 0.9 0.50
    2 Propiconazole Trans-2-nonenoic acid 0.02225 0.009766 0.4 0.75
    3 Propiconazole Trans-2-decenoic acid 0.02225 0.009766 0.4 0.75
    4 Propiconazole 9-Decenoic acid 0.02225 0.009766 0.9 0.38
    5 Propiconazole Trans-2-undecenoic acid 0.02225 0.009766 0.4 0.75
  • TABLE 40
    Growth inhibition of Sclerotinia sclerotiorum by epoxiconazole,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Epoxiconazole 0.03
    Trans-2-nonenoic acid 0.019531
    Trans-2-decenoic acid 0.019531
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.078125
    1 Epoxiconazole Trans-2-nonenoic acid 0.0075 0.009766 1.3 0.75
    2 Epoxiconazole Trans-2-decenoic acid 0.0075 0.009766 1.3 0.75
    3 Epoxiconazole 3-Decenoic acid 0.0075 0.019531 2.6 0.50
    4 Epoxiconazole 9-Decenoic acid 0.0075 0.019531 2.6 0.50
  • TABLE 41
    Growth inhibition of Sclerotinia sclerotiorum by tebuconazole,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Tebuconazole 0.1125
    Trans-3-hexenoic acid 0.15625
    3-Heptenoic acid 0.078125
    Trans-2-nonenoic acid 0.039062
    3-Nonenoic acid 0.039062
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.078125
    Trans-2-undecenoic acid 0.039062
    1 Tebuconazole Trans-3-hexenoic acid 0.05625 0.039062 0.7 0.75
    2 Tebuconazole 3-Heptenoic acid 0.05625 0.019531 0.3 0.75
    3 Tebuconazole Trans-2-nonenoic acid 0.028125 0.004882 0.2 0.38
    4 Tebuconazole 3-Nonenoic acid 0.05625 0.009766 0.2 0.75
    5 Tebuconazole 3-Decenoic acid 0.028125 0.009766 0.3 0.38
    6 Tebuconazole 9-Decenoic acid 0.028125 0.009766 0.3 0.38
    7 Tebuconazole Trans-2-undecenoic acid 0.05625 0.009766 0.2 0.75
  • TABLE 42
    Growth inhibition of Sclerotinia sclerotiorum by tebuconazole,
    in combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Tebuconazole 0.1125
    Trans-3-octanoic acid 0.039062
    Trans-2-decenoic acid 0.019531
    1 Tebuconazole Trans-3-octanoic acid 0.028125 0.019531 0.7 0.75
    2 Tebuconazole Trans-2-decenoic acid 0.028125 0.004882 0.2 0.50
    • Example 13: Growth Inhibition of Botrytis cinerea by Pyraclostrobin, Azoxystrobin, Chlorothalonil, Cyprodinil, Metalaxyl, Epoxiconazole, and Tebuconazole, in Combination with Various Exemplary Unsaturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, chlorothalonil, cyprodinil, metalaxyl, epoxiconazole, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 43-50 below. Working solutions of (2E,4E)-2,4-hexadienoic acid, trans-2-hexenoic acid, trans-3-hexenoic acid, 5-hexenoic acid, 3-heptenoic acid, trans-2-octenoic acid, trans-3-octenoic acid, 3-octenoic acid, 7-octenoic acid, 3-decenoic acid, 9-decenoic acid, trans-2-nonenoic acid, 3-nonenoic acid, (9Z)-octadecenoic acid, trans-2-decenoic acid, and trans-2-undecenoic acid (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 43-50 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 48 hours, and the FIC Index for each combination calculated, as shown in Tables 43-50 below.
  • TABLE 43
    Growth inhibition of Botrytis cinerea by pyraclostrobin, in
    combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.001875
    (2E,4E)-2,4-hexadienoic 0.0625
    acid
    Trans-2-hexenoic acid 0.078125
    Trans-3-hexenoic acid 0.15625
    4-Hexenoic acid 0.3125
    5-Hexenoic acid 0.15625
    3-Heptenoic acid 0.078125
    Trans-2-octenoic acid 0.039062
    3-Octenoic acid 0.078125
    Trans-3-octenoic acid 0.078125
    7-Octenoic acid 0.078125
    Trans-2-nonenoic acid 0.078125
    3-Nonenoic acid 0.078125
    Trans-2-decenoic acid 0.019531
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.15625
    Trans-2-undecenoic acid 0.15625
    1 Pyraclostrobin (2E,4E)-2,4-hexadienoic 0.000469 0.007812 17 0.38
    acid
    2 Pyraclostrobin Trans-2-hexenoic acid 0.000937 0.009766 10 0.63
    3 Pyraclostrobin Trans-3-hexenoic acid 0.000469 0.009766 21 0.31
    4 Pyraclostrobin 4-Hexenoic acid 0.000937 0.019531 21 0.56
    5 Pyraclostrobin 5-Hexenoic acid 0.000469 0.009766 21 0.31
    6 Pyraclostrobin 3-Heptenoic acid 0.000469 0.004882 10 0.31
    7 Pyraclostrobin Trans-2-octenoic acid 0.000234 0.002441 10 0.19
    8 Pyraclostrobin 3-Octenoic acid 0.000234 0.002441 10 0.16
    9 Pyraclostrobin Trans-3-octenoic acid 0.000469 0.004882 10 0.31
    10 Pyraclostrobin 7-Octenoic acid 0.000469 0.004882 10 0.31
    11 Pyraclostrobin Trans-2-nonenoic acid 0.000469 0.004882 10 0.31
    12 Pyraclostrobin 3-Nonenoic acid 0.000469 0.004882 10 0.31
    13 Pyraclostrobin Trans-2-decenoic acid 0.000469 0.004882 10 0.50
    14 Pyraclostrobin 3-Decenoic acid 0.000234 0.004882 21 0.19
    15 Pyraclostrobin 9-Decenoic acid 0.000234 0.002441 10 0.14
    16 Pyraclostrobin Trans-2-undecenoic acid 0.000937 0.009766 10 0.56
  • TABLE 44
    Growth inhibition of Botrytis cinerea by pyraclostrobin, in
    combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.001875
    (2E,4E)-2,4-hexadienoic 0.0625
    acid
    Trans-2-hexenoic acid 0.039062
    Trans-3-hexenoic acid 0.15625
    5-Hexenoic acid 0.078125
    3-Heptenoic acid 0.078125
    Trans-2-octenoic acid 0.039062
    3-Octenoic acid 0.078125
    7-Octenoic acid 0.039062
    Trans-2-nonenoic acid 0.039062
    3-Nonenoic acid 0.078125
    Trans-2-decenoic acid 0.078125
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.078125
    Trans-2-undecenoic acid 0.078125
    1 Pyraclostrobin (2E,4E)-2,4-hexadienoic 0.000234 0.003906 17 0.19
    acid
    2 Pyraclostrobin Trans-2-hexenoic acid 0.000234 0.002441 10 0.19
    3 Pyraclostrobin Trans-3-hexenoic acid 0.000469 0.009766 21 0.31
    4 Pyraclostrobin 5-Hexenoic acid 0.000469 0.009766 21 0.38
    5 Pyraclostrobin 3-Heptenoic acid 0.000469 0.004882 10 0.19
    6 Pyraclostrobin Trans-2-octenoic acid 0.000234 0.002441 10 0.19
    7 Pyraclostrobin 3-Octenoic acid 0.000469 0.004882 10 0.31
    8 Pyraclostrobin 7-Octenoic acid 0.000234 0.002441 10 0.19
    9 Pyraclostrobin Trans-2-nonenoic acid 0.000234 0.002441 10 0.19
    10 Pyraclostrobin 3-Nonenoic acid 0.000469 0.004882 10 0.31
    11 Pyraclostrobin Trans-2-decenoic acid 0.000234 0.002441 10 0.16
    12 Pyraclostrobin 3-Decenoic acid 0.000234 0.004882 21 0.19
    13 Pyraclostrobin 9-Decenoic acid 0.000234 0.002441 10 0.16
    14 Pyraclostrobin Trans-2-undecenoic acid 0.000234 0.002441 10 0.16
  • TABLE 45
    Growth inhibition of Botrytis cinerea by azoxystrobin, in combination
    with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Azoxystrobin 0.075
    Trans-2-hexenoic acid 0.15625
    Trans-3-hexenoic acid 0.3125
    4-Hexenoic acid 0.3125
    5-Hexenoic acid 0.3125
    Trans-2-octenoic acid 0.078125
    3-Octenoic acid 0.078125
    Trans-3-octenoic acid 0.15625
    7-Octenoic acid 0.15625
    Trans-2-nonenoic acid 0.039062
    3-Nonenoic acid 0.078125
    Trans-2-decenoic acid 0.039062
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.078125
    Trans-2-undecenoic acid 0.078125
    1 Azoxystrobin Trans-2-hexenoic acid 0.0375 0.039062 1 0.75
    3 Azoxystrobin Trans-3-hexenoic acid 0.0375 0.078125 2 0.75
    4 Azoxystrobin 4-Hexenoic acid 0.0375 0.078125 2 0.75
    5 Azoxystrobin 5-Hexenoic acid 0.0375 0.078125 2 0.75
    6 Azoxystrobin Trans-2-octenoic acid 0.009375 0.009766 1 0.25
    7 Azoxystrobin 3-Octenoic acid 0.01875 0.019531 1 0.50
    8 Azoxystrobin Trans-3-octenoic acid 0.01875 0.019531 1 0.38
    9 Azoxystrobin 7-Octenoic acid 0.01875 0.019531 1 0.38
    10 Azoxystrobin Trans-2-nonenoic acid 0.01875 0.019531 1 0.75
    11 Azoxystrobin 3-Nonenoic acid 0.01875 0.019531 1 0.50
    12 Azoxystrobin Trans-2-decenoic acid 0.009375 0.009766 1 0.38
    13 Azoxystrobin 3-Decenoic acid 0.009375 0.019531 2 0.38
    14 Azoxystrobin 9-Decenoic acid 0.01875 0.019531 1 0.50
    15 Azoxystrobin Trans-2-undecenoic acid 0.01875 0.019531 1 0.50
  • TABLE 46
    Growth inhibition of Botrytis cinerea by chlorothalonil, in
    combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Chlorothalonil 1.758 × 10−5
    Trans-2-nonenoic acid 0.019531
    9-Decenoic acid 0.039062
    1 Chlorothalonil Trans-2-nonenoic acid 4.395 × 10−6 0.004882 1111 0.50
    2 Chlorothalonil 9-Decenoic acid 4.395 × 10−6 0.019531 4444 0.75
  • TABLE 47
    Growth inhibition of Botrytis cinerea by cyprodinil, in combination
    with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Cyprodinil 0.0045
    3-Heptenoic acid 0.078125
    Trans-2-octenoic acid 0.078125
    3-Octenoic acid 0.078125
    7-Octenoic acid 0.078125
    Trans-2-nonenoic acid 0.078125
    3-Nonenoic acid 0.078125
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.078125
    Trans-2-undecenoic acid 0.078125
    1 Cyprodinil 3-Heptenoic acid 0.001125 0.039062 35 0.75
    2 Cyprodinil Trans-2-octenoic acid 0.001125 0.039062 35 0.75
    3 Cyprodinil 3-Octenoic acid 0.001125 0.039062 35 0.75
    4 Cyprodinil 7-Octenoic acid 0.000562 0.019531 35 0.38
    5 Cyprodinil Trans-2-nonenoic acid 0.001125 0.039062 35 0.75
    6 Cyprodinil 3-Nonenoic acid 0.001125 0.039062 35 0.75
    7 Cyprodinil 3-Decenoic acid 0.000562 0.039062 69 0.63
    8 Cyprodinil 9-Decenoic acid 0.000562 0.019531 35 0.38
    9 Cyprodinil Trans-2-undecenoic acid 0.000562 0.019531 35 0.38
  • TABLE 48
    Growth inhibition of Botrytis cinerea by metalaxyl, in combination
    with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Metalaxyl 0.316
    3-Nonenoic acid 0.078125
    9-Decenoic acid 0.078125
    Trans-2-undecenoic acid 0.078125
    1 Metalaxyl 3-Nonenoic acid 0.079 0.039062 0.5 0.75
    2 Metalaxyl 9-Decenoic acid 0.079 0.039062 0.5 0.75
    3 Metalaxyl Trans-2-undecenoic acid 0.079 0.039062 0.5 0.75
  • TABLE 49
    Growth inhibition of Botrytis cinerea by epoxiconazole, in
    combination with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Epoxiconazole 0.03
    3-Heptenoic acid 0.078125
    Trans-2-octenoic acid 0.15625
    3-Octenoic acid 0.078125
    Trans-3-octenoic acid 0.078125
    Trans-2-nonenoic acid 0.15625
    3-Nonenoic acid 0.078125
    Trans-2-decenoic acid 0.078125
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.15625
    Trans-2-undecenoic acid 0.078125
    (9Z)-octadecenoic acid 5.0
    1 Epoxiconazole 3-Heptenoic acid 0.0075 0.039062 5 0.75
    2 Epoxiconazole Trans-2-octenoic acid 0.0075 0.039062 5 0.50
    3 Epoxiconazole 3-Octenoic acid 0.0075 0.039062 5 0.75
    4 Epoxiconazole Trans-3-octenoic acid 0.0075 0.039062 5 0.75
    5 Epoxiconazole Trans-2-nonenoic acid 0.00375 0.019531 5 0.25
    6 Epoxiconazole 3-Nonenoic acid 0.00375 0.019531 5 0.38
    7 Epoxiconazole Trans-2-decenoic acid 0.00375 0.019531 5 0.38
    8 Epoxiconazole 3-Decenoic acid 0.001875 0.019531 10 0.31
    9 Epoxiconazole 9-Decenoic acid 0.00375 0.019531 5 0.25
    10 Epoxiconazole Trans-2-undecenoic acid 0.0075 0.039062 5 0.75
    11 Epoxiconazole (9Z)-octadecenoic acid 0.015 2.5 167 1.00
  • TABLE 50
    Growth inhibition of Botrytis cinerea by tebuconazole, in combination
    with various exemplary unsaturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Tebuconazole 0.1125
    5-Hexenoic acid 0.15625
    Trans-2-octenoic acid 0.039062
    Trans-2-decenoic acid 0.039062
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.039062
    Trans-2-undecenoic acid 0.039062
    (9Z)-octadecenoic acid 5.0
    1 Tebuconazole 5-Hexenoic acid 0.028125 0.039062 1.4 0.50
    2 Tebuconazole Trans-2-octenoic acid 0.014062 0.009766 0.7 0.38
    3 Tebuconazole Trans-2-decenoic acid 0.028125 0.019531 0.7 0.75
    4 Tebuconazole 3-Decenoic acid 0.028125 0.019531 0.7 0.50
    5 Tebuconazole 9-Decenoic acid 0.014062 0.019531 1.4 0.63
    6 Tebuconazole Trans-2-undecenoic acid 0.028125 0.019531 0.7 0.75
    7 Tebuconazole (9Z)-octadecenoic acid 0.015 2.5 44 1.00
    • Example 15: Growth Inhibition of Botrytis cinerea by Pyraclostrobin, Azoxystrobin, Cyprodinil, Difenoconazole, Epoxiconazole and Tebuconazole, in Combination with Various Exemplary Hydroxy-Substituted Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, cyprodinil, difenoconazole, epoxiconazole and tebuconazole, were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Table 51 below. Working solutions of 3-hydroxybutyric acid, 3-hydroxyhexanoic acid and 3-hydroxydecanoic acid (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Table 51 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the growth inhibition assay, observed following an incubation period of 48 hours, and the FIC Index for each combination calculated, as shown in Table 51 below.
  • TABLE 51
    Growth inhibition of Botrytis cinerea by various synthetic fungicides
    in combination with various exemplary saturated aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.015
    Azoxystrobin 0.15
    Cyprodinil 0.009
    Difenoconazole 0.0255
    Epoxiconazole 0.03
    Tebuconazole 0.1125
    3-hydroxybutyric acid 10
    3-hydroxyhexanoic acid 2.5
    3-hydroxydecanoic acid 0.125
    1 Pyraclostrobin 3-hydroxybutyric acid 0.00375 2.5 667 0.50
    2 Azoxystrobin 3-hydroxybutyric acid 0.0375 5 133 0.75
    3 Cyprodinil 3-hydroxybutyric acid 0.00225 5 2222 0.75
    4 Cyprodinil 3-hydroxyhexanoic acid 0.00225 1.25 556 0.75
    5 Cyprodinil 3-hydroxydecanoic acid 0.00225 0.0625 28 0.75
    6 Difenoconazole 3-hydroxybutyric acid 0.01275 2.5 196 0.75
    7 Difenoconazole 3-hydroxyhexanoic acid 0.01275 0.625 49 0.75
    8 Difenoconazole 3-hydroxydecanoic acid 0.01275 0.03125 2 0.75
    9 Epoxiconazole 3-hydroxybutyric acid 0.0075 2.5 333 0.50
    10 Tebuconazole 3-hydroxybutyric acid 0.01406 1.25 89 0.25
    • Example 16: Growth Inhibition of Fusarium oxysporum by Pyraclostrobin, Azoxystrobin, Fludioxonil, and Tebuconazole, in Combination with Various Exemplary Hydroxy-Substituted Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, fludioxonil, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 52-54 below. Working solutions of 2-hydroxybutyric acid, 2-hydroxyhexanoic acid, 2-hydroxyoctanoic acid, 3-hydroxyoctanoic acid, 8-hydroxyoctanoic acid, and 10-hydroxydecanoic acid, (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 52-54 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 48 hours, and the FIC Index for each combination calculated, as shown in Tables 52-54 below.
  • TABLE 52
    Growth inhibition of Fusarium oxysporum by various synthetic fungicides
    in combination with exemplary hydroxy-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.015
    Azoxystrobin 0.15
    Tebuconazole 0.1125
    3-Hydroxyoctanoic acid 1.25
    8-Hydroxyoctanoic acid 5
    1 Pyraclostrobin 3-Hydroxyoctanoic acid 0.0075 0.3125 42 0.75
    2 Pyraclostrobin 8-Hydroxyoctanoic acid 0.0075 1.25 167 0.75
    3 Azoxystrobin 3-Hydroxyoctanoic acid 0.075 0.3125 4 0.75
    4 Azoxystrobin 8-Hydroxyoctanoic acid 0.075 1.25 17 0.75
    7 Tebuconazole 8-Hydroxyoctanoic acid 0.05625 0.625 11 0.63
  • TABLE 53
    Growth inhibition of Fusarium oxysporum by pyraclostrobin in
    combination with an exemplary hydroxy-substituted aliphatic acid
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.015
    10-Hydroxydecanoic 1
    acid
    1 Pyraclostrobin 10-Hydroxydecanoic 0.00375 0.25 67 0.50
    acid
  • TABLE 54
    Growth inhibition of Fusarium oxysporum by various synthetic fungicides
    in combination with various exemplary hydroxy-substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.015
    Fludioxonil 0.021
    Azoxystrobin 0.15
    Tebuconazole 0.225
    2-Hydroxybutyric acid 5
    2-Hydroxyhexanoic acid 2.5
    2-Hydroxyoctanoic acid 0.625
    1 Pyraclostrobin 2-Hydroxybutyric acid 0.00375 1.25 333 0.50
    2 Pyraclostrobin 2-Hydroxyhexanoic acid 0.00375 0.625 167 0.50
    3 Fludioxonil 2-Hydroxybutyric acid 0.00525 1.25 238 0.50
    4 Fludioxonil 2-Hydroxyhexanoic acid 0.00525 0.625 119 0.50
    5 Fludioxonil 2-Hydroxyoctanoic acid 0.00525 0.15625 30 0.50
    6 Azoxystrobin 2-Hydroxybutyric acid 0.0375 1.25 33 0.50
    7 Azoxystrobin 2-Hydroxyhexanoic acid 0.0375 0.625 17 0.50
    8 Tebuconazole 2-Hydroxyhexanoic acid 0.05625 0.625 11 0.50
    • Example 17: Growth Inhibition of Sclerotinia sclerotiorum by Pyraclostrobin, Azoxystrobin, Fludioxonil, Difenoconazole, and Tebuconazole, in Combination with Various Exemplary Hydroxy-Substituted Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, fludioxonil, difenoconazole, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 55-57 below. Working solutions of 2-hydroxybutyric acid, 2-hydroxyhexanoic acid, 2-hydroxyoctanoic acid, 3-hydroxyoctanoic acid, 8-hydroxyoctanoic acid, 10-hydroxydecanoic acid, and 12-hydroxydodecanoic acid (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 55-57 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 7 days, and the FIC Index for each combination calculated, as shown in Tables 55-57 below.
  • TABLE 55
    Growth inhibition of Sclerotinia sclerotiorum by by various synthetic fungicides
    in combination with various exemplary hydroxy-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0075
    Azoxystrobin 0.15
    Fludioxonil 3.28125 × 10−4
    Tebuconazole 0.05625
    3-hydroxyoctanoic acid 0.625
    8-hydroxyoctanoic acid 5
    1 Pyraclostrobin 3-hydroxyoctanoic acid 0.001875 0.15625 83 0.50
    2 Pyraclostrobin 8-hydroxyoctanoic acid  9.375 × 10−4 0.3125 333 0.19
    3 Azoxystrobin 3-hydroxyoctanoic acid 0.0375 0.15625 4 0.50
    4 Azoxystrobin 8-hydroxyoctanoic acid 0.0375 0.625 17 0.38
    5 Fludioxonil 8-hydroxyoctanoic acid 8.20315 × 10−5 1.25 15238 0.50
    6 Tebuconazole 3-hydroxyoctanoic acid 0.028125 0.15625 6 0.75
    7 Tebuconazole 8-hydroxyoctanoic acid 0.028125 0.625 22 0.63
  • TABLE 56
    Growth inhibition of Sclerotinia sclerotiorum by various synthetic fungicides
    in combination with various exemplary hydroxy-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0075
    Azoxystrobin 0.15
    Fludioxonil 3.28125 × 10−4
    Difenoconazole 0.0255
    10-hydroxydecanoic acid 0.5
    12-hydroxydodecanoic 0.1
    acid
    1 Pyraclostrobin 10-hydroxydecanoic acid 0.001875 0.125 67 0.50
    2 Pyraclostrobin 12-hydroxydodecanoic 0.001875 0.025 13 0.50
    acid
    3 Azoxystrobin 10-hydroxydecanoic acid 0.0375 0.125 3 0.50
    4 Fludioxonil 10-hydroxydecanoic acid 8.20315 × 10−5 0.25 3048 0.75
    5 Difenoconazole 12-hydroxydodecanoic 0.006375 0.025 4 0.50
    acid
  • TABLE 57
    Growth inhibition of Sclerotinia sclerotiorum by various synthetic fungicides
    in combination with various exemplary hydroxy-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0075
    Fludioxonil 3.281 × 10−4
    Difenoconazole 0.0255
    Azoxystrobin 0.15
    Tebuconazole 0.1125
    2-Hydroxybutyric acid 2.5
    2-Hydroxyhexanoic acid 2.5
    2-Hydroxyoctanoic acid 0.3125
    1 Pyraclostrobin 2-Hydroxybutyric acid 0.001875 1.25 667 0.75
    2 Pyraclostrobin 2-Hydroxyhexanoic acid 0.001875 0.625 333 0.50
    3 Pyraclostrobin 2-Hydroxyoctanoic acid 0.001875 0.15625 83 0.75
    4 Fludioxonil 2-Hydroxybutyric acid 4.101 × 10−5 1.25 30476 0.63
    5 Fludioxonil 2-Hydroxyhexanoic acid 4.101 × 10−5 0.625 15238 0.38
    6 Fludioxonil 2-Hydroxyoctanoic acid 4.101 × 10−5 0.15625 3810 0.63
    7 Difenoconazole 2-Hydroxybutyric acid 0.006375 1.25 196 0.75
    8 Difenoconazole 2-Hydroxyhexanoic acid 0.006375 0.625 98 0.50
    9 Azoxystrobin 2-Hydroxybutyric acid 0.0375 1.25 33 0.75
    10 Azoxystrobin 2-Hydroxyhexanoic acid 0.0375 0.625 17 0.50
    11 Azoxystrobin 2-Hydroxyoctanoic acid 0.0375 0.15625 4 0.75
    12 Tebuconazole 2-Hydroxybutyric acid 0.01406 0.625 44 0.38
    13 Tebuconazole 2-Hydroxyhexanoic acid 0.028125 0.625 22 0.50
    14 Tebuconazole 2-Hydroxyoctanoic acid 0.028125 0.15625 6 0.75
    • Example 18: Growth Inhibition of Botryrtis cinerea by Various Exemplary Synthetic Fungicides, in Combination with Various Exemplary Hydroxy-Substituted Saturated Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, fludioxonil, tebuconazole, and difenoconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 58-61 below. Working solutions of 2-hydroxybutyric, 2-hydroxyhexanoic, 2-hydroxyoctanoic, 10-hydroxydecanoic, 12-hydroxydodecanoic, 3-hydroxyoctanoic, 8-hydroxyoctanoic acids, (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 58-61 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 2 days, and the FIC Index for each combination calculated, as shown in Tables 58-61 below.
  • TABLE 58
    Growth inhibition of Botrytis cinerea by various exemplary synthetic fungicides
    in combination with various exemplary hydroxy-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.015
    Azoxystrobin 0.15
    Difenoconazole 0.051
    Tebuconazole 0.1125
    3-hydroxyoctanoic acid 0.625
    8-hydroxyoctanoic acid 2.5
    1 Pyraclostrobin 3-hydroxyoctanoic acid 0.00375 0.15625 42 0.50
    2 Pyraclostrobin 8-hydroxyoctanoic acid 0.00375 0.625 167 0.50
    3 Azoxystrobin 3-hydroxyoctanoic acid 0.0375 0.3125 8 0.75
    4 Azoxystrobin 8-hydroxyoctanoic acid 0.0375 1.25 33 0.75
    5 Difenoconazole 8-hydroxyoctanoic acid 0.006375 0.3125 49 0.25
    6 Tebuconazole 3-hydroxyoctanoic acid 0.003516 0.01953 6 0.06
    7 Tebuconazole 8-hydroxyoctanoic acid 0.001758 0.03906 22 0.03
  • TABLE 59
    Growth inhibition of Botrytis cinerea by various exemplary synthetic fungicides
    in combination with various exemplary hydroxy-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.015
    Fludioxonil 1.641 × 10−4
    Tebuconazole 0.1125
    3-Hydroxyoctanoic acid 0.625
    8-Hydroxyoctanoic acid 2.5
    10-Hydroxydecanoic 0.5
    acid
    12-Hydroxydodecanoic 0.05
    acid
    1 Pyraclostrobin 12-Hydroxydodecanoic 0.00375 0.025 7 0.75
    acid
    2 Fludioxonil 3-Hydroxyoctanoic acid 4.103 × 10−5 0.019531 476 0.28
    3 Fludioxonil 8-Hydroxyoctanoic acid 4.103 × 10−5 0.078125 1904 0.28
    4 Tebuconazole 10-Hydroxydecanoic 0.003516 0.015625 4 0.06
    acid
  • TABLE 60
    Growth inhibition of Botrytis cinerea by various exemplary synthetic fungicides
    in combination with various exemplary hydroxy-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Comp FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Comp A Index
    Azoxystrobin 0.15
    12-Hydroxydodecanoic acid 0.1
    1 Azoxystrobin 12-Hydroxydodecanoic acid 0.0375 0.05 1.33 0.75
  • TABLE 61
    Growth inhibition of Botrytis cinerea by various exemplary synthetic fungicides
    in combination with various exemplary hydroxy-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Comp FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Comp A Index
    Pyraclostrobin 0.015
    Azoxystrobin 0.15
    Difenoconazole 0.051
    2-hydroxybutyric acid 5
    2-hydroxyhexanoic acid 2.5
    2-hydroxyoctanoic acid 0.625
    1 Pyraclostrobin 2-hydroxyoctanoic acid 0.00375 0.15625 42 0.50
    2 Azoxystrobin 2-hydroxybutyric acid 0.0375 2.5 67 0.75
    3 Azoxystrobin 2-hydroxyhexanoic acid 0.0375 1.25 33 0.75
    4 Azoxystrobin 2-hydroxyoctanoic acid 0.0375 0.3125 8 0.75
    5 Difenoconazole 2-hydroxybutyric acid 0.01275 1.25 98 0.50
    • Example 19: Growth Inhibition of Sclerotinta Sclerotiorum by Pyraclostrobin, Azoxystrobin, Fludioxonil, and Tebuconazole, in Combination with Various Exemplary Alkyl-Substituted Aliphatic Acids
  • Working solutions ofpyraclostrobin, azoxystrobin, fludioxonil, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 62-66 below. Working solutions of2,2-diethylbutanoic acid, 3-methylbutyric acid, 2-ethylhexanoic acid, 3-methylhexanoic acid, 4-methylhexanoc acid, and 2-methyloctanoic acid, (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 62-66 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 7 days, and the FIC Index for each combination calculated, as shown in Tables 62-66 below.
  • TABLE 62
    Growth inhibition of Sclerotinia sclerotiorum by various exemplary synthetic fungicides
    in combination with various exemplary alkyl-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0075
    Fludioxonil 3.281 × 10−4
    Azoxystrobin 0.15
    Tebuconazole 0.1125
    2,2-Diethylbutanoic acid 0.25
    3-Methylbutyric acid 0.625
    Pyraclostrobin 2,2-Diethylbutanoic acid 0.001875 0.0625 33 0.50
    Pyraclostrobin 3-Methylbutyric acid 9.375 × 10−4 0.078125 83 0.25
    Fludioxonil 2,2-Diethylbutanoic acid 4.101 × 10−5 0.0625 1524 0.38
    Fludioxonil 3-Methylbutyric acid 4.101 × 10−5 0.15625 3810 0.38
    Azoxystrobin 3-Methylbutyric acid 0.0375 0.15625 4 0.50
    Tebuconazole 2,2-Diethylbutanoic acid 0.028125 0.0625 2 0.50
    Tebuconazole 3-Methylbutyric acid 0.028125 0.15625 6 0.50
  • TABLE 63
    Growth inhibition of Sclerotinia sclerotiorum by various exemplary synthetic
    fungicides in combination with an exemplary alkyl-substituted aliphatic acid
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0075 
    Azoxystrobin 0.15  
    Fludioxonil 3.28125 × 10−4
    Difenoconazole 0.01275
    Tebuconazole 0.05625
    2-Ethylhexanoic acid 0.625
    1 Pyraclostrobin 2-Ethylhexanoic acid 2.34375 × 10−4 0.009766 42 0.05
    2 Azoxystrobin 2-Ethylhexanoic acid 0.01875 0.039062 2 0.19
    3 Fludioxonil 2-Ethylhexanoic acid 4.10158 × 10−5 0.078125 1905 0.25
    4 Difenoconazole 2-Ethylhexanoic acid  0.006375 0.078125 12 0.63
    5 Tebuconazole 2-Ethylhexanoic acid  0.028125 0.078125 3 0.63
  • TABLE 64
    Growth inhibition of Sclerotinia sclerotiorum by various exemplary synthetic
    fungicides in combination with an exemplary alkyl-substituted aliphatic acid
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0075
    Azoxystrobin 0.15 
    Fludioxonil 3.2813 × 10−4
    2-Methyloctanoic acid 0.078125
    1 Pyraclostrobin 2-Methyloctanoic acid  9.375 × 10−4 0.009766 10 0.25
    2 Azoxystrobin 2-Methyloctanoic acid 0.0375 0.019531 0.5 0.50
    3 Fludioxonil 2-Methyloctanoic acid 4.10158 × 10−5  0.019531 476 0.38
  • TABLE 65
    Growth inhibition of Sclerotinia sclerotiorum by various exemplary synthetic
    fungicides in combination with an exemplary alkyl-substituted aliphatic acid
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.0075
    Fludioxonil 3.28125 × 10−4
    3-Methylhexanoic acid 0.125
    1 Pyraclostrobin 3-Methylhexanoic acid  9.375 × 10−4 0.015625 17 0.25
    2 Fludioxonil 3-Methylhexanoic acid 8.20315 × 10−5 0.0625 762 0.75
  • TABLE 66
    Growth inhibition of Sclerotinia sclerotiorum by pyraclostrobin
    in combination with an exemplary alkyl-substituted aliphatic acid
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Pyraclostrobin 0.00375
    4-Methylhexanoic acid 0.078125
    1 Pyraclostrobin 4-Methylhexanoic acid 9.375 × 10−4 0.009766 10 0.38
    • Example 20: Growth Inhibition of Botrytis cinerea by Pyraclostrobin, Azoxystrobin, Difenoconazole, and Tebuconazole, in Combination with Various Exemplary Alkyl-Substituted Aliphatic Acids
  • Working solutions of pyraclostrobin, azoxystrobin, difenoconazole, and tebuconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 67-70 below. Working solutions of 2,2-diethylbutanoic acid, 3-methylbutyric acid, 2-ethylhexanoic acid, 3-methylhexanoic acid, 4-methylhexanoic acid, and 2-methyloctanoic acid, and 2-methyldecanoic acid (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 67-70 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 48 hours, and the FIC Index for each combination calculated, as shown in Tables 67-70 below.
  • TABLE 67
    Growth inhibition of Botrytis cinerea by various exemplary synthetic fungicides
    in combination with various exemplary alkyl-substituted aliphatic acids
    MIC (A) MIC (B) Ratio Comp FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Comp A Index
    Pyraclostrobin 0.0015
    Difenoconazole 0.051
    Azoxystrobin 0.15
    Tebuconazole 0.1125
    2,2-Diethylbutanoic acid 0.25
    4-Methylhexanoic acid 0.15625
    2-Methyloctanoic acid 0.078125
    1 Pyraclostrobin 4-Methylhexanoic acid 0.00375 0.03906 10 0.50
    2 Difenoconazole 2,2-Diethylbutanoic acid 0.01275 0.0625 5 0.50
    3 Difenoconazole 4-Methylhexanoic acid 0.01275 0.03906 3 0.50
    4 Difenoconazole 2-Methyloctanoic acid 0.01275 0.019531 2 0.50
    5 Azoxystrobin 4-Methylhexanoic acid 0.01875 0.039062 2 0.38
    6 Tebuconazole 2,2-Diethylbutanoic acid 0.001758 0.003906 2 0.03
    7 Tebuconazole 4-Methylhexanoic acid 0.003516 0.004883 1.4 0.06
    8 Tebuconazole 2-Methyloctanoic acid 0.001758 0.001221 0.7 0.03
  • TABLE 68
    Growth inhibition of Botrytis cinerea by various exemplary synthetic fungicides
    in combination with an exemplary alkyl-substituted aliphatic acid
    MIC (A) MIC (B) Ratio Comp FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Comp A Index
    Pyraclostrobin 0.015
    Difenoconazole 0.051
    Tebuconazole 0.1125
    2-Ethylhexanoic acid 0.3125
    1 Pyraclostrobin 2-Ethylhexanoic acid 0.0075 0.078125 10 0.75
    2 Difenoconazole 2-Ethylhexanoic acid 0.0255 0.078125 3 0.75
    3 Tebuconazole 2-Ethylhexanoic acid 0.003516 0.004883 1 0.05
  • TABLE 69
    Growth inhibition of Botrytis cinerea by various exemplary synthetic fungicides
    in combination with an exemplary alkyl-substituted aliphatic acid
    MIC (A) MIC (B) Ratio Comp FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Comp A Index
    Pyraclostrobin 0.015
    Azoxystrobin 0.15
    Tebuconazole 0.1125
    3-Methylhexanoic acid 0.125
    1 Pyraclostrobin 3-Methylhexanoic acid 0.00375 0.03125 8 0.50
    2 Azoxystrobin 3-Methylhexanoic acid 0.0375 0.0625 2 0.75
    3 Tebuconazole 3-Methylhexanoic acid 0.001758 0.001953 1 0.03
  • TABLE 70
    Growth inhibition of Botrytis cinerea by various exemplary synthetic fungicides
    in combination with various exemplary alkyl-substituted aliphatic acids
    MIC (A) MIC (B) Ratio CompB/ FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) Comp A Index
    Pyraclostrobin 0.015
    Difenoconazole 0.051
    2-Methyldecanoic acid 0.015625
    3-Methylbutyric acid 0.3125
    Pyraclostrobin 2-Methyldecanoic acid 0.00375 0.0078125 2 0.75
    1 Pyraclostrobin 3-Methylbutyric acid 0.00375 0.15625 42 0.75
    2 Difenoconazole 3-Methylbutyric acid 0.006375 0.078125 12 0.38
    • Example 21: Growth Inhibition of Botrytis cinerea by Picoxystrobin, Mancozeb, Isopyrazam, Oxathiapiprolin, Penthiopyrad, Prothioconazole and Trifloxystrobin, in Combination with Various Exemplary C4-C10 Saturated, Unsaturated, Hydroxy-, Methyl-, Ethyl-, and Diethyl-Substituted Aliphatic Acids
  • Working solutions of picoxystrobin, mancozeb, isopyrazam, oxathiapiprolin, penthiopyrad, prothioconazole, and trifloxystrobin, were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 71-79 below. Working solutions of 2-hydroxybutyric acid, 2-hydroxyhexanoic acid, 2-hydroxyoctanoic acid, 3-hydroxybutyric acid, 3-hydroxyhexanoic acid, 3-hydroxyoctanoic acid, 3-hydroxydecanoic acid, 8-hydroxyoctanoic acid, 10-hydroxydecanoic acid, 12-hydroxydodecanoic acid, 2,2-diethylbutanoic acid, 2-ethylhexanoic acid, 2-methyloctanoic acid, 2-methyldecanoic acid, 3-methylbutyric acid, 3-methylhexanoic acid, 3-methylnonanoic acid, 4-methylhexanoic acid, hexanoic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, 2,4-hexedienoic acid, trans-2-hexenoic acid, trans-2-octenoic acid, trans-3-octenoic acid, 7-octenoic acid, trans-2-nonenoic acid, trans-2-decenoic acid, 3-decenoic acid, 9-decenoic acid, trans-2-undecenoic acid, 2-hydroxybutyric acid, 3-hydroxybutyric acid, 3-hydroxyhexanoic acid, 3-hydroxyoctanoic acid, 3-hydroxydecanoic acid, 8-hydroxyoctanoic acid, 12-hydroxydodecanoic acid, 2-methyloctanoic acid, 2-methyldecanoic acid, and oleic acid (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 71-79 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 48 hours, and the FIC Index for each combination calculated, as shown in Tables 71-79 below.
  • TABLE 71
    Growth inhibition of Botrytis cinerea by picoxystrobin, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Picoxystrobin 0.25
    Trans-2-decenoic acid 0.019531
    2-Hydroxybutyric acid 5
    2-Hydroxyhexanoic acid 1.25
    2-Hydroxyoctanoic acid 0.625
    3-Hydroxybutyric acid 10
    3-Hydroxyhexanoic acid 2.5
    3-Hydroxyoctanoic acid 0.625
    3-Hydroxydecanoic acid 0.0625
    8-Hydroxyoctanoic acid 1.25
    10-Hydroxydecanoic acid 0.25
    12-Hydroxydodecanoic 0.1
    acid
    2,2-Diethylbutanoic acid 0.25
    2-Ethylhexanoic acid 0.15625
    2-Methyloctanoic acid 0.039062
    2-Methyldecanoic acid 0.0078125
    3-Methylbutyric acid 0.3125
    3-Methylhexanoic acid 0.125
    3-Methylnonanoic acid 0.015625
    4-Methylhexanoic acid 0.078125
    1 Picoxystrobin Trans-2-decenoic acid 0.015625 0.004883 0.31 0.31
    2 Picoxystrobin 2-Hydroxybutyric acid 0.015625 0.625 40 0.19
    3 Picoxystrobin 2-Hydroxyhexanoic acid 0.015625 0.3125 20 0.31
    4 Picoxystrobin 2-Hydroxyoctanoic acid 0.015625 0.078125 5 0.19
    5 Picoxystrobin 3-Hydroxybutyric acid 0.015625 1.25 80 0.19
    6 Picoxystrobin 3-Hydroxyhexanoic acid 0.015625 0.3125 20 0.19
    7 Picoxystrobin 3-Hydroxyoctanoic acid 0.03125 0.15625 5 0.38
    8 Picoxystrobin 3-Hydroxydecanoic acid 0.015625 0.015625 1 0.31
    9 Picoxystrobin 8-Hydroxyoctanoic acid 0.015625 0.3125 20 0.31
    10 Picoxystrobin 10-Hydroxydecanoic acid 0.015625 0.0625 4 0.31
    11 Picoxystrobin 12-Hydroxydodecanoic 0.03125 0.025 0.8 0.38
    acid
    12 Picoxystrobin 2,2-Diethylbutanoic acid 0.015625 0.03125 2 0.19
    13 Picoxystrobin 2-Ethylhexanoic acid 0.015625 0.019531 1.25 0.19
    14 Picoxystrobin 2-Methyloctanoic acid 0.0078125 0.004883 0.6 0.16
    15 Picoxystrobin 2-Methyldecanoic acid 0.015625 0.003906 0.25 0.56
    16 Picoxystrobin 3-Methylbutyric acid 0.015625 0.078125 5 0.31
    17 Picoxystrobin 3-Methylhexanoic acid 0.015625 0.015625 1 0.19
    18 Picoxystrobin 3-Methylnonanoic acid 0.015625 0.001953 0.13 0.19
    19 Picoxystrobin 4-Methylhexanoic acid 0.015625 0.019531 1.25 0.31
  • TABLE 72
    Growth inhibition of Botrytis cinerea by picoxystrobin, in
    combination with various exemplary unsaturated aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Picoxystrobin 0.25
    Decanoic acid 0.015625
    Trans-2-hexenoic 0.15625
    acid
    Picoxystrobin Decanoic acid 0.03125 0.0078125 0.25 0.63
    Picoxystrobin Trans-2-hexenoic 0.0625 0.019531 0.3 0.38
    acid
  • TABLE 73
    Growth inhibition of Botrytis cinerea by mancozeb, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Mancozeb 0.03125
    Trans-2-octenoic acid 0.039062
    3-Decenoic acid 0.039062
    1 Mancozeb Trans-2-octenoic acid 0.003906 0.019531 5 0.63
    2 Mancozeb 3-Decenoic acid 0.003906 0.019531 5 0.63
  • TABLE 74
    Growth inhibition of Botrytis cinerea by isopyrazam, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Isopyrazam 0.03125
    Hexanoic acid 0.15625
    Octanoic acid 0.3125
    Decanoic acid 0.015625
    Dodecanoic acid 0.05
    2,4-Dihexenoic acid 0.125
    5-Hexenoic acid 0.3125
    7-Octenoic acid 0.3125
    3-Nonenoic acid 0.078125
    Trans-3-octenoic acid 0.039062
    3-Decenoic acid 0.039062
    9-Decenoic acid 0.078125
    Oleic acid 5
    1 Isopyrazam Hexanoic acid 0.0078125 0.03906 5 0.50
    2 Isopyrazam Octanoic acid 0.0078125 0.019531 2.5 0.31
    3 Isopyrazam Decanoic acid 0.0039062 0.0078125 2 0.63
    4 Isopyrazam Dodecanoic acid 0.0078125 0.0125 1.6 0.50
    5 Isopyrazam 2,4-Dihexenoic acid 0.0078125 0.0625 8 0.75
    6 Isopyrazam 5-Hexenoic acid 0.0078125 0.039062 5 0.38
    7 Isopyrazam 7-Octenoic acid 0.0078125 0.019531 2.5 0.31
    8 Isopyrazam 3-Nonenoic acid 0.0078125 0.019531 2.5 0.50
    9 Isopyrazam Trans-3-octenoic acid 0.0078125 0.019531 2.5 0.75
    10 Isopyrazam 3-Decenoic acid 0.0078125 0.019531 2.5 0.75
    11 Isopyrazam 9-Decenoic acid 0.0078125 0.019531 2.5 0.50
    12 Isopyrazam Oleic acid 0.03125 5 160 2.0
  • TABLE 75
    Growth inhibition of Botrytis cinerea by oxathiapiprolin, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Oxathiapiprolin 0.5
    12-Hydroxydodecanoic 0.1
    acid
    2-Hydroxybutyric acid
    1 Oxathiapiprolin 12-Hydroxydodecanoic 0.125 0.025 0.2 0.50
    acid
    2 Oxathiapiprolin 2-Hydroxybutyric acid 0.125 1.25 10 0.75
  • TABLE 76
    Growth inhibition of Botrytis cinerea by penthiopyrad, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Penthiopyrad 0.25
    Hexanoic acid 0.15625
    Octanoic acid 0.3125
    Nonanoic acid 0.078125
    Decanoic acid 0.03125
    Dodecanoic acid 0.05
    (2E,4E)-2,4-Hexadienoic 0.125
    acid
    Trans-2-hexenoic acid 0.3125
    Trans-2-octenoic acid 0.078125
    Trans-3-octenoic acid 0.078125
    7-Octenoic acid 0.3125
    Trans-2-nonenoic acid 0.15625
    Trans-2-decenoic acid 0.078125
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.078125
    Trans-2-undecenoic acid 0.039062
    2-Hydroxybutyric acid 2.5
    3-Hydroxybutyric acid 10
    3-Hydroxyhexanoic acid 5
    3-Hydroxyoctanoic acid 0.625
    3-Hydroxydecanoic acid 0.125
    8-Hydroxyoctanoic acid 2.5
    12-Hydroxydodecanoic 0.1
    acid
    2-Methyloctanoic acid 0.3125
    2-Methyldecanoic acid 0.125
    Oleic acid 5
    1 Penthiopyrad Hexanoic acid 0.0625 0.039062 0.6 0.50
    2 Penthiopyrad Octanoic acid 0.0625 0.019531 0.3 0.31
    3 Penthiopyrad Nonanoic acid 0.0625 0.019531 0.3 0.50
    4 Penthiopyrad Decanoic acid 0.03125 0.0078125 0.25 0.38
    5 Penthiopyrad Dodecanoic acid 0.0625 0.0125 0.2 0.50
    6 Penthiopyrad (2E,4E)-2,4-Hexadienoic 0.0625 0.0625 1 0.75
    acid
    7 Penthiopyrad Trans-2-hexenoic acid 0.0625 0.019531 0.3 0.31
    8 Penthiopyrad Trans-2-octenoic acid 0.0625 0.019531 0.3 0.50
    9 Penthiopyrad Trans-3-octenoic acid 0.0625 0.019531 0.3 0.50
    10 Penthiopyrad 7-Octenoic acid 0.0625 0.019531 0.3 0.31
    11 Penthiopyrad Trans-2-nonenoic acid 0.0625 0.009766 0.16 0.31
    12 Penthiopyrad Trans-2-decenoic acid 0.03125 0.004883 0.16 0.19
    13 Penthiopyrad 3-Decenoic acid 0.0625 0.019531 0.3 0.50
    14 Penthiopyrad 9-Decenoic acid 0.0625 0.019531 0.3 0.50
    15 Penthiopyrad Trans-2-undecenoic acid 0.0625 0.019531 0.3 0.63
    16 Penthiopyrad 2-Hydroxybutyric acid 0.0625 1.25 20 0.75
    17 Penthiopyrad 3-Hydroxybutyric acid 0.0625 2.5 40 0.50
    18 Penthiopyrad 3-Hydroxyhexanoic acid 0.0625 0.625 10 0.38
    19 Penthiopyrad 3-Hydroxyoctanoic acid 0.0625 0.15625 2.5 0.50
    20 Penthiopyrad 3-Hydroxydecanoic acid 0.0625 0.03125 0.5 0.50
    21 Penthiopyrad 8-Hydroxyoctanoic acid 0.03125 0.3125 10 0.25
    22 Penthiopyrad 12-Hydroxydodecanoic 0.0625 0.025 0.4 0.50
    acid
    23 Penthiopyrad 2-Methyloctanoic acid 0.0625 0.019531 0.3 0.31
    24 Penthiopyrad 2-Methyldecanoic acid 0.03125 0.0039062 0.13 0.16
    25 Penthiopyrad Oleic acid 0.125 2.5 20 1.0
  • TABLE 77
    Growth inhibition of Botrytis cinerea by prothioconazole, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Prothioconazole 0.03125
    2-Hydroxybutyric 2.5
    acid
    1 Prothioconazole 2-Hydroxybutyric 0.0078125 1.25 160 0.75
    acid
  • TABLE 78
    Growth inhibition of Botrytis cinerea by trifloxystrobin, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Trifloxystrobin 0.25
    Hexanoic acid 0.3125
    Octanoic acid 0.625
    Decanoic acid 0.03125
    (2E,4E)-2,4-Hexadienoic 0.25
    acid
    Trans-2-octenoic acid 0.078125
    Trans-2-decenoic acid 0.15625
    3-Decenoic acid 0.15625
    9-Decenoic acid 0.15625
    Trans-2-undecenoic acid 0.15625
    1 Trifloxystrobin Hexanoic acid 0.03125 0.039062 1.25 0.25
    2 Trifloxystrobin Octanoic acid 0.03125 0.019531 0.6 0.16
    3 Trifloxystrobin Decanoic acid 0.03125 0.015625 0.5 0.63
    4 Trifloxystrobin (2E,4E)-2,4-Hexadienoic 0.03125 0.0625 2 0.38
    acid
    5 Trifloxystrobin Trans-2-octenoic acid 0.03125 0.019531 0.6 0.38
    6 Trifloxystrobin Trans-2-decenoic acid 0.03125 0.009766 0.3 0.19
    7 Trifloxystrobin 3-Decenoic acid 0.03125 0.019531 0.6 0.25
    8 Trifloxystrobin 9-Decenoic acid 0.03125 0.019531 0.6 0.25
    9 Trifloxystrobin Trans-2-undecenoic acid 0.03125 0.019531 0.6 0.25
  • TABLE 79
    Growth inhibition of Botrytis cinerea by trifloxystrobin, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Trifloxystrobin 0.25
    Heptanoic acid 0.078125
    Nonanoic acid 0.078125
    2-Hydroxybutyric acid 2.5
    2-hydroxyhexanoic acid 1.25
    2-Hydroxydecanoic acid 0.3125
    3-Hydroxybutyric acid 5
    3-Hydroxyhexanoic acid 2.5
    3-Hydroxyoctanoic acid 0.625
    3-Hydroxydecanoic acid 0.125
    8-Hydroxyoctanoic acid 1.25
    10-Hydroxydecanoic acid 0.25
    12-Hydroxydodecanoic 0.05
    acid
    2,2-Diethylbutanoic acid 0.25
    2-Ethylhexanoic acid 0.15625
    2-Methyloctanoic acid 0.078125
    2-Methyldecanoic acid 0.125
    3-Methylbutyric acid 0.3125
    3-Methylhexanoic acid 0.125
    4-Methylhexanoic acid 0.078125
    1 Trifloxystrobin Heptanoic acid 0.03125 0.019531 0.6 0.38
    2 Trifloxystrobin Nonanoic acid 0.015625 0.009766 0.6 0.19
    3 Trifloxystrobin 2-Hydroxybutyric acid 0.03125 1.25 40 0.63
    4 Trifloxystrobin 2-hydroxyhexanoic acid 0.03125 0.625 20 0.63
    5 Trifloxystrobin 2-Hydroxydecanoic acid 0.03125 0.15625 5 0.63
    6 Trifloxystrobin 3-Hydroxybutyric acid 0.03125 2.5 80 0.63
    7 Trifloxystrobin 3-Hydroxyhexanoic acid 0.03125 0.625 20 0.38
    8 Trifloxystrobin 3-Hydroxyoctanoic acid 0.03125 0.15625 5 0.38
    9 Trifloxystrobin 3-Hydroxydecanoic acid 0.03125 0.03125 1 0.38
    10 Trifloxystrobin 8-Hydroxyoctanoic acid 0.03125 0.625 20 0.63
    11 Trifloxystrobin 10-Hydroxydecanoic acid 0.03125 0.125 4 0.63
    12 Trifloxystrobin 12-Hydroxydodecanoic 0.03125 0.025 0.8 0.63
    acid
    13 Trifloxystrobin 2,2-Diethylbutanoic acid 0.03125 0.0625 2 0.38
    14 Trifloxystrobin 2-Ethylhexanoic acid 0.015625 0.019531 1.25 0.19
    15 Trifloxystrobin 2-Methyloctanoic acid 0.015625 0.009766 0.6 0.19
    16 Trifloxystrobin 2-Methyldecanoic acid 0.015625 0.0039062 0.25 0.09
    17 Trifloxystrobin 3-Methylbutyric acid 0.03125 0.15625 5 0.63
    18 Trifloxystrobin 3-Methylhexanoic acid 0.03125 0.03125 1 0.38
    19 Trifloxystrobin 4-Methylhexanoic acid 0.015625 0.019531 1.25 0.31
    • Example 22: Growth Inhibition of Alternaria Solani by Picoxystrobin, Mancozeb, Penthiopyrad, and Prothioconazole, in Combination with Various Exemplary C4-C10 Saturated, Unsaturated, Hydroxy-, Methyl-, Ethyl-, and Diethyl-Substituted Aliphatic Acids
  • Working solutions of picoxystrobin, mancozeb, penthiopyrad, and prothioconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 80-84 below. Working solutions of 2-hydroxybutyric acid, 2-hydroxyoctanoi c acid, 2-ethylhexanoi c acid, 2-methyloctanoic acid, 2-methyldecanoic acid, 3-methylhexanoic acid, 3-methylnonanoic acid, 4-methylhexanoic acid, hexanoic acid, heptanoic, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, 2,4-hexedienoic acid, trans-3-hexenoic acid, 5-hexenoic acid, 3-heptenoic acid, trans-2-octenoic acid, 3-octenoic acid, trans-3-octenoic acid, trans-2-nonenoic acid, 3-nonenoic acid, trans-2-decenoic acid, cis-3-hexenoic acid, 7-octenoic acid, 3-decenoic acid, 9-decenoic acid, trans-2-undecenoic acid, 2-hydroxybutyric acid, 3-hydroxybutyric acid, 3-hydroxyhexanoic acid, 3-hydroxyoctanoic acid, 3-hydroxydecanoic acid, 8-hydroxyoctanoic acid, 12-hydroxydodecanoic acid, 2-methyloctanoic acid, 2-methyldecanoic acid, and oleic acid (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 80-84 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 7 days, and the FIC Index for each combination calculated, as shown in Tables 80-84 below.
  • TABLE 80
    Growth inhibition of Alternaria solani by picoxystrobin, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Picoxystrobin 0.5
    Hexanoic acid 0.15625
    Heptanoic acid 0.15625
    Octanoic acid 0.15625
    Nonanoic acid 0.15625
    Decanoic acid 0.03125
    Dodecanoic acid 0.1
    (2E,4E)-2,4-Hexadienoic 0.125
    acid
    Trans-3-hexenoic acid 0.3125
    5-Hexenoic acid 0.3125
    3-Heptenoic acid 0.3125
    Trans-2-octenoic acid 0.078125
    3-Octenoic acid 0.15625
    Trans-3-octenoic acid 0.15625
    Trans-2-nonenoic acid 0.078125
    3-Nonenoic acid 0.078125
    Trans-2-decenoic acid 0.078125
    3-Decenoic acid 0.078125
    9-Decenoic acid 0.03906
    Trans-2-undecenoic acid 0.15625
    1 Picoxystrobin Hexanoic acid 0.125 0.039062 0.3 0.50
    2 Picoxystrobin Heptanoic acid 0.0625 0.019531 0.3 0.25
    3 Picoxystrobin Octanoic acid 0.03125 0.019531 0.6 0.19
    4 Picoxystrobin Nonanoic acid 0.0625 0.009766 0.16 0.19
    5 Picoxystrobin Decanoic acid 0.0625 0.0078125 0.13 0.38
    6 Picoxystrobin Dodecanoic acid 0.0625 0.0125 0.2 0.25
    7 Picoxystrobin (2E,4E)-2,4-Hexadienoic 0.0625 0.03125 0.5 0.38
    acid
    8 Picoxystrobin Trans-3-hexenoic acid 0.125 0.078125 0.6 0.50
    9 Picoxystrobin 5-Hexenoic acid 0.125 0.078125 0.6 0.50
    10 Picoxystrobin 3-Heptenoic acid 0.125 0.039062 0.3 0.38
    11 Picoxystrobin Trans-2-octenoic acid 0.125 0.019531 0.16 0.50
    12 Picoxystrobin 3-Octenoic acid 0.125 0.039062 0.3 0.50
    13 Picoxystrobin Trans-3-octenoic acid 0.0625 0.019531 0.3 0.25
    14 Picoxystrobin Trans-2-nonenoic acid 0.03125 0.019531 0.6 0.31
    15 Picoxystrobin 3-Nonenoic acid 0.0625 0.019531 0.3 0.38
    16 Picoxystrobin Trans-2-decenoic acid 0.125 0.039062 0.3 0.75
    17 Picoxystrobin 3-Decenoic acid 0.0625 0.019531 0.3 0.38
    18 Picoxystrobin 9-Decenoic acid 0.0625 0.019531 0.3 0.63
    19 Picoxystrobin Trans-2-undecenoic acid 0.0625 0.019531 0.3 0.25
  • TABLE 81
    Growth inhibition of Alternaria solani by picoxystrobin, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Picoxystrobin 0.5
    Trans-2-decenoic acid 0.039062
    Cis-3-hexenoic acid 0.3125
    7-Octenoic acid 0.15625
    3-Hydroxyoctanoic acid 1.25
    8-Hydroxyoctanoic acid 2.5
    10-Hydroxydecanoic acid 1
    12-Hydroxydodecanoic 0.1
    acid
    2-Hydroxybutyric acid 2.5
    2-Hydroxyoctanoic acid 0.625
    2-Ethylhexanoic acid 0.15625
    2-Methyloctanoic acid 0.15625
    3-Methylhexanoic acid 0.25
    3-Methylnonanoic acid 0.0625
    4-Methylhexanoic acid 0.3125
    2-Methyldecanoic acid 0.125
    1 Picoxystrobin Trans-2-decenoic acid 0.0625 0.019531 0.3 0.63
    2 Picoxystrobin Cis-3-hexenoic acid 0.125 0.078125 0.6 0.50
    3 Picoxystrobin 7-Octenoic acid 0.0625 0.019531 0.3 0.25
    4 Picoxystrobin 3-Hydroxyoctanoic acid 0.125 0.15625 1.25 0.38
    5 Picoxystrobin 8-Hydroxyoctanoic acid 0.125 0.625 5 0.50
    6 Picoxystrobin 10-Hydroxydecanoic acid 0.125 0.125 1 0.38
    7 Picoxystrobin 12-Hydroxydodecanoic 0.125 0.025 0.2 0.50
    acid
    8 Picoxystrobin 2-Hydroxybutyric acid 0.125 0.625 5 0.50
    9 Picoxystrobin 2-Hydroxyoctanoic acid 0.125 0.15625 1.25 0.50
    10 Picoxystrobin 2-Ethylhexanoic acid 0.125 0.039062 0.3 0.50
    11 Picoxystrobin 2-Methyloctanoic acid 0.0625 0.019531 0.3 0.25
    12 Picoxystrobin 3-Methylhexanoic acid 0.125 0.03125 0.25 0.38
    13 Picoxystrobin 3-Methylnonanoic acid 0.125 0.015625 0.13 0.50
    14 Picoxystrobin 4-Methylhexanoic acid 0.125 0.039062 0.3 0.38
    15 Picoxystrobin 2-Methyldecanoic acid 0.125 0.03125 0.25 0.50
  • TABLE 82
    Growth inhibition of Alternaria solani by penthiopyrad, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Penthiopyrad 0.5
    Octanoic acid 0.3125
    Trans-2-nonenoic acid 0.15625
    Trans-3-octenoic acid 0.15625
    1 Penthiopyrad Octanoic acid 0.0625 0.039062 0.6 0.25
    2 Penthiopyrad Trans-2-nonenoic acid 0.125 0.078125 0.6 0.75
    3 Penthiopyrad Trans-3-octenoic acid 0.125 0.039062 0.3 0.50
  • TABLE 83
    Growth inhibition of Alternaria solani by prothioconazole, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Prothioconazole 0.5
    2-Hydroxybutyric acid 2.5
    2-Hydroxyhexanoic 2.5
    acid
    3-Hydroxybutyric acid 5
    3-Hydroxyhexanoic 2.5
    acid
    8-Hydroxyoctanoic acid 2.5
    2-Ethylhexanoic acid 0.3125
    3-Methylnonanoic acid 0.0625
    2-Methyldecanoic acid 1
    3-Methylbutyric acid 0.3125
    1 Prothioconazole 2-Hydroxybutyric acid 0.125 0.625 5 0.50
    2 Prothioconazole 2-Hydroxyhexanoic 0.125 0.625 5 0.50
    acid
    3 Prothioconazole 3-Hydroxybutyric acid 0.125 1.25 10 0.50
    4 Prothioconazole 3-Hydroxyhexanoic 0.125 0.625 5 0.50
    acid
    5 Prothioconazole 8-Hydroxyoctanoic acid 0.125 0.625 5 0.50
    6 Prothioconazole 2-Ethylhexanoic acid 0.125 0.039062 0.3 0.38
    7 Prothioconazole 3-Methylnonanoic acid 0.125 0.015625 0.13 0.50
    8 Prothioconazole 2-Methyldecanoic acid 0.125 0.03125 0.25 0.28
    9 Prothioconazole 3-Methylbutyric acid 0.125 0.078125 0.6 0.50
  • TABLE 84
    Growth inhibition of Alternaria solani by mancozeb, in combination with
    various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Mancozeb 0.5
    Heptanoic acid 0.15625
    2-Methyloctanoic acid 0.625
    2-Methyldecanoic acid 1
    1 Mancozeb Heptanoic acid 0.125 0.039062 0.3 0.50
    2 Mancozeb 2-Methyloctanoic acid 0.125 0.039062 0.3 0.31
    3 Mancozeb 2-Methyldecanoic acid 0.125 0.03125 0.25 0.28
    • Example 23: Growth Inhibition of Sclerotinia sclerotiorum by Picoxystrobin, Penthiopyrad, and Prothioconazole, in Combination with Various Exemplary C4-C10 Saturated, Unsaturated, Hydroxy-, Methyl-, and Ethyl-Substituted Aliphatic Acids
  • Working solutions of picoxystrobin, penthiopyrad, and prothioconazole were each prepared as described above (as Compound A) and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 85-88 below. Working solutions of 2-hydroxybutyric acid, 2-hydroxyoctanoic acid, 2-ethylhexanoic acid, 3-methylbutyric acid, nonanoic acid, trans-3-hexenoic acid, 3-heptenoic acid, trans-2-nonenoic acid, trans-2-decenoic acid, 3-decenoic acid, 9-decenoic acid, and 10-hydroxydecanoic acid (as Compound B), were each prepared as described above, and were serially diluted in PDB to the individual required concentrations for MIC testing as shown in Tables 85-88 below.
  • Each individual compound and combination was tested over a range of 2-fold dilutions in the synergistic growth inhibition assay, observed following an incubation period of 7 days, and the FIC Index for each combination calculated, as shown in Tables 85-88 below.
  • TABLE 85
    Growth inhibition of Sclerotinia sclerotiorum by picoxystrobin, in combination
    with various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Picoxystrobin 0.5
    Nonanoic acid 0.039062
    Trans-2-octenoic acid 0.039062
    3-Nonenoic acid 0.078125
    3-Decenoic acid 0.15625
    1 Picoxystrobin Nonanoic acid 0.125 0.019531 0.16 0.75
    2 Picoxystrobin Trans-2-octenoic acid 0.125 0.009766 0.08 0.50
    3 Picoxystrobin 3-Nonenoic acid 0.125 0.019531 0.16 0.50
    4 Picoxystrobin 3-Decenoic acid 0.125 0.019531 0.16 0.38
  • TABLE 86
    Growth inhibition of Sclerotinia sclerotiorum by picoxystrobin, in combination
    with various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Picoxystrobin 0.5
    Trans-2-decenoic acid 0.019531
    10-Hydroxydecanoic acid 0.5
    2-Hydroxybutyric acid 5
    2-Hydroxyoctanoic acid 0.625
    2-Ethylhexanoic acid 0.15625
    3-Methylbutyric acid 0.625
    1 Picoxystrobin Trans-2-decenoic acid 0.125 0.004883 0.04 0.5
    2 Picoxystrobin 10-Hydroxydecanoic acid 0.125 0.125 1 0.50
    3 Picoxystrobin 2-Hydroxybutyric acid 0.125 1.25 10 0.50
    4 Picoxystrobin 2-Hydroxyoctanoic acid 0.125 0.15625 1.25 0.50
    5 Picoxystrobin 2-Ethylhexanoic acid 0.125 0.078125 0.625 0.75
    6 Picoxystrobin 3-Methylbutyric acid 0.125 0.15625 1.25 0.50
  • TABLE 87
    Growth inhibition of Sclerotinia sclerotiorum by penthiopyrad, in combination
    with various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Penthiopyrad 0.5
    Trans-3-hexenoic acid 0.3125
    3-Heptenoic acid 0.15625
    Trans-2-nonenoic acid 0.078125
    3-Decenoic acid 0.15625
    9-Decenoic acid 0.078125
    1 Penthiopyrad Trans-3-hexenoic acid 0.125 0.039062 0.3 0.38
    2 Penthiopyrad 3-Heptenoic acid 0.125 0.019531 0.16 0.38
    3 Penthiopyrad Trans-2-nonenoic acid 0.125 0.019531 0.16 0.50
    4 Penthiopyrad 3-Decenoic acid 0.125 0.019531 0.16 0.38
    5 Penthiopyrad 9-Decenoic acid 0.125 0.019531 0.16 0.50
  • TABLE 88
    Growth inhibition of Sclerotinia sclerotiorum by prothioconazole, in combination
    with various exemplary saturated, unsaturated, and substituted aliphatic acids.
    MIC (A) MIC (B) Ratio Compound FIC
    Combination Compound A Compound B (mg/mL) (mg/mL) B/Compound A Index
    Prothioconazole 0.0625
    2-Hydroxybutyric acid 5
    1 Prothioconazole 2-Hydroxybutyric acid 0.015625 1.25 80 0.50
  • Predictive Methods
  • In the experimental methods and results listed above, synergistic efficacy is shown for many exemplary synergistic pesticidal compositions according to some embodiments of the present disclosure, such synergistic pesticidal compositions comprising at least a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12) saturated or unsaturated aliphatic acid or salt thereof. In addition to the above listed experimental methods, it is desirable to additionally employ predictive methods for predicting synergistic efficacy of a pesticidal composition comprising at least a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12) saturated or unsaturated aliphatic acid or salt thereof. Accordingly, a synergistic composition predictive model was constructed using neural network machine learning computational techniques, to provide a synergistic compound screening system that is trained using experimentally determined in vitro results showing synergistic and non-synergistic pesticidal efficacy of pesticidal compositions comprising a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12) saturated or unsaturated aliphatic acid or salt thereof, and which determines a probability of synergistic efficacy of a specific such pesticidal composition.
  • In one embodiment of the present disclosure, a synergistic composition predictive system was constructed using an ensemble of machine learning models, and which provides a predicted probability that a candidate pesticidal composition comprising a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12) saturated or unsaturated aliphatic acid or salt thereof will exhibit synergistic pesticidal efficacy in vitro against a target pathogen or pest. Each individual predictive model within the ensemble was initialized differently and each such model was trained using a selected portion of an in vitro synergistic pesticidal composition training dataset, leaving a remaining portion of the dataset for validation of each individual predictive model. This approach allows for a diversity between the individual predictive models in the ensemble, resulting in improved average predictive accuracy of the combined predictions of synergy across the ensemble of models, for a particular candidate pesticidal composition comprising a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12) saturated or unsaturated aliphatic acid or salt. In the present predictive method, a separate synergistic composition predictive model was constructed for predicting probability of synergy of a candidate pesticidal composition for each of three exemplary target pathogens or pests, including Fusarium oxysporum, Botrytis cinerea, and Sclerotinia sclerotiorum, and each such model was trained using an experimentally obtained dataset of in vitro synergistic efficacy results for a multiplicity of in vitro screened pesticidal compositions comprising a pesticidal active ingredient and a C4-C10 (or in alternative embodiments, alternatively C11 or C12). Each such model was validated using non-training portions of the in vitro experimental synergistic pesticidal composition dataset for the relevant pathogen, to determine and optimize its predictive performance in predicting in vitro synergy.
  • In some embodiments, Fusarium oxysporum was used as a representative pest organism or pathogen to determine a predicted probability of synergy for pesticidal compositions comprising a pesticidal active ingredient agent (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent or salt thereof (compound B). In other embodiments, Botrytis cinerea was used as a representative pest organism or pathogen to determine a predicted probability of synergy for pesticidal compositions comprising a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent or salt thereof (compound B). In further embodiments, Sclerotinia sclerotiorum was used as a representative pest organism or pathogen to determine a predicted probability of synergy for pesticidal compositions comprising a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent or salt thereof (compound B). In some embodiments, an exemplary threshold of predicted probability of synergy greater than 55% (or 0.55) was applied to determine exemplary predictions of in vitro synergistic interaction between a pesticidal active ingredient (compound A) and one or more C4-C10 (or alternatively C11 or C12) saturated or unsaturated aliphatic acid agent or salt thereof (compound B) in a synergistic pesticidal composition. Results of exemplary predictions of in vitro synergistic pesticidal efficacy against an exemplary pathogen or pest made using a synergistic composition predictive system as described above are shown in the following Tables 89-91.
    • PREDICTED EXAMPLES
  • Example 24: Predicted synergistic efficacy for in vitro growth inhibition of Fusarium oxysporum by benzovindiflupyr, bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, oxathiapiprolin, penflufen, penthiopyrad, picoxystrobin, prothioconazole, pydiflumetofen, revysol, sedaxane, trifloxystrobin, and valifenalate, in combination with various exemplary saturated and unsaturated C4-C12 aliphatic acids, according to an embodiment of the present disclosure.
  • A prediction of probability of synergistic efficacy for each combination of benzovindiflupyr, bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, oxathiapiprolin, penflufen, penthiopyrad, picoxystrobin, prothioconazole, pydiflumetofen, revysol, sedaxane, trifloxystrobin, and valifenalate (Compound A) and a saturated or unsaturated aliphatic acid (Compound B) compound was determined using a synergistic composition predictive model trained using an experimental in vitro synergistic efficacy dataset for in vitro growth inhibition of Fusarium oxysporum. The resulting synergistic efficacy predictions are shown in Table 89 below.
  • TABLE 89
    Predicted synergistic efficacy for in vitro growth inhibition of Fusarium oxysporum
    by benzovindiflupyr, bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine,
    florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl,
    metrafenone, oxathiapiprolin, penflufen, penthiopyrad, picoxystrobin, prothioconazole,
    pydiflumetofen, revysol, sedaxane, trifloxystrobin, and valifenalate, in combination
    with various exemplary saturated and unsaturated C4-C12 aliphatic acids according
    to an embodiment of the present disclosure
    Predicted
    Probability of Synergistic
    Synergistic Efficacy
    Combination Compound A Compound B Efficacy Prediction
    1 Benzovindiflupyr 2-aminohexanoic acid 0.5767963 Likely
    2 Benzovindiflupyr 2-hydroxyoctanoic acid 0.55433092 Likely
    3 Benzovindiflupyr 3-hydroxydecanoic acid 0.55428505 Likely
    4 Benzovindiflupyr 2-hydroxybutyric acid 0.55139626 Likely
    5 Benzovindiflupyr 2-hydroxyhexanoic acid 0.55136665 Likely
    6 Benzovindiflupyr 2-aminobutyric acid 0.55121322 Likely
    7 Bixafen 2-aminohexanoic acid 0.5986134 Likely
    8 Bixafen 3-hydroxydecanoic acid 0.59260478 Likely
    9 Bixafen 2-hydroxyoctanoic acid 0.59127055 Likely
    10 Bixafen 2-hydroxyhexanoic acid 0.58412244 Likely
    11 Bixafen 3-hydroxyoctanoic acid 0.58250974 Likely
    12 Bixafen 2-hydroxybutyric acid 0.58020663 Likely
    13 Bixafen 2-aminobutyric acid 0.57291304 Likely
    14 Bixafen 8-hydroxyoctanoic acid 0.55678314 Likely
    15 Bixafen 3-hydroxyhexanoic acid 0.55412076 Likely
    16 Boscalid 2-aminohexanoic acid 0.56465167 Likely
    17 Boscalid 2-hydroxybutyric acid 0.55472363 Likely
    18 Boscalid 2-hydroxyoctanoic acid 0.55112691 Likely
    19 Cyproconazole 2-aminohexanoic acid 0.57628425 Likely
    20 Fenpicoxamid 2-aminohexanoic acid 0.58695443 Likely
    21 Fenpicoxamid 2-aminobutyric acid 0.56769621 Likely
    22 Fenpicoxamid 2-hydroxybutyric acid 0.56525598 Likely
    23 Fenpicoxamid 2-hydroxyhexanoic acid 0.55343788 Likely
    24 Fenpyrazamine 2-aminohexanoic acid 0.59352859 Likely
    25 Fenpyrazamine 3-hydroxydecanoic acid 0.58132785 Likely
    26 Fenpyrazamine 2-aminobutyric acid 0.5700103 Likely
    27 Fenpyrazamine 2-hydroxyoctanoic acid 0.55568954 Likely
    28 Fenpyrazamine 8-hydroxyoctanoic acid 0.55427292 Likely
    29 Fenpyrazamine 3-aminobutyric acid 0.55375423 Likely
    30 Fenpyrazamine 3-hydroxyoctanoic acid 0.5508373 Likely
    31 Florylpicoxamid 2-aminohexanoic acid 0.63476055 Likely
    32 Florylpicoxamid 2-hydroxybutyric acid 0.61054637 Likely
    33 Florylpicoxamid 2-aminobutyric acid 0.60774106 Likely
    34 Florylpicoxamid 2-hydroxyhexanoic acid 0.60711867 Likely
    35 Florylpicoxamid 2-hydroxyoctanoic acid 0.60666923 Likely
    36 Florylpicoxamid 3-hydroxyoctanoic acid 0.59813283 Likely
    37 Florylpicoxamid 3-hydroxydecanoic acid 0.58653796 Likely
    38 Florylpicoxamid 3-hydroxyhexanoic acid 0.58024375 Likely
    39 Florylpicoxamid octanoic acid 0.57787609 Likely
    40 Florylpicoxamid heptanoic acid 0.57581491 Likely
    41 Florylpicoxamid hexanoic acid 0.57327745 Likely
    42 Florylpicoxamid decanoic acid 0.56412624 Likely
    43 Florylpicoxamid 3-aminobutyric acid 0.56136031 Likely
    44 Florylpicoxamid 3-hydroxybutyric acid 0.56075103 Likely
    45 Florylpicoxamid nonanoic acid 0.55557516 Likely
    46 Florylpicoxamid dodecanoic acid 0.55174383 Likely
    47 Flutriafol 2-aminohexanoic acid 0.64187107 Likely
    48 Flutriafol 2-aminobutyric acid 0.61206777 Likely
    49 Flutriafol 2-hydroxybutyric acid 0.61086082 Likely
    50 Flutriafol 2-hydroxyhexanoic acid 0.60704852 Likely
    51 Flutriafol 2-hydroxyoctanoic acid 0.60100349 Likely
    52 Flutriafol 3-hydroxydecanoic acid 0.59106896 Likely
    53 Flutriafol 3-hydroxyoctanoic acid 0.58686044 Likely
    54 Flutriafol 3-hydroxyhexanoic acid 0.56472518 Likely
    55 Flutriafol 3-aminobutyric acid 0.55888988 Likely
    56 Fluxapyroxad 2-aminohexanoic acid 0.65365264 Likely
    57 Fluxapyroxad 2-hydroxyoctanoic acid 0.63406985 Likely
    58 Fluxapyroxad 3-hydroxydecanoic acid 0.63228451 Likely
    59 Fluxapyroxad 2-aminobutyric acid 0.63064658 Likely
    60 Fluxapyroxad 2-hydroxybutyric acid 0.62910696 Likely
    61 Fluxapyroxad 2-hydroxyhexanoic acid 0.62872769 Likely
    62 Fluxapyroxad 3-hydroxyoctanoic acid 0.62480617 Likely
    63 Fluxapyroxad 3-hydroxyhexanoic acid 0.59925105 Likely
    64 Fluxapyroxad 3-aminobutyric acid 0.59057821 Likely
    65 Fluxapyroxad 8-hydroxyoctanoic acid 0.58737963 Likely
    66 Fluxapyroxad octanoic acid 0.58452264 Likely
    67 Fluxapyroxad 3-hydroxybutyric acid 0.5824682 Likely
    68 Fluxapyroxad heptanoic acid 0.58077161 Likely
    69 Fluxapyroxad 10-hydroxydecanoic acid 0.57686063 Likely
    70 Fluxapyroxad nonanoic acid 0.57673815 Likely
    71 Fluxapyroxad hexanoic acid 0.57447241 Likely
    72 Fluxapyroxad decanoic acid 0.5742406 Likely
    73 Fluxapyroxad dodecanoic acid 0.56431965 Likely
    74 Isopyrazam 2-aminohexanoic acid 0.59632861 Likely
    75 Isopyrazam 3-hydroxydecanoic acid 0.58139259 Likely
    76 Isopyrazam 2-hydroxyoctanoic acid 0.58047971 Likely
    77 Isopyrazam 2-aminobutyric acid 0.57527404 Likely
    78 Isopyrazam 2-hydroxyhexanoic acid 0.57359112 Likely
    79 Isopyrazam 2-hydroxybutyric acid 0.57283605 Likely
    80 Isopyrazam 3-hydroxyoctanoic acid 0.56890551 Likely
    81 Isotianil 2-aminohexanoic acid 0.55867075 Likely
    82 Kresoxim-methyl 2-aminohexanoic acid 0.67504148 Likely
    83 Kresoxim-methyl 2-aminobutyric acid 0.65768701 Likely
    84 Kresoxim-methyl 2-hydroxyhexanoic acid 0.65029321 Likely
    85 Kresoxim-methyl 2-hydroxyoctanoic acid 0.64980065 Likely
    86 Kresoxim-methyl 2-hydroxybutyric acid 0.64942813 Likely
    87 Kresoxim-methyl 3-hydroxydecanoic acid 0.6411885 Likely
    88 Kresoxim-methyl 3-hydroxyoctanoic acid 0.63833933 Likely
    89 Kresoxim-methyl 3-aminobutyric acid 0.62326319 Likely
    90 Kresoxim-methyl 3-hydroxyhexanoic acid 0.62174223 Likely
    91 Kresoxim-methyl octanoic acid 0.61937875 Likely
    92 Kresoxim-methyl heptanoic acid 0.6178017 Likely
    93 Kresoxim-methyl hexanoic acid 0.6141121 Likely
    94 Kresoxim-methyl nonanoic acid 0.61324196 Likely
    95 Kresoxim-methyl decanoic acid 0.6072263 Likely
    96 Kresoxim-methyl 3-hydroxybutyric acid 0.60505759 Likely
    97 Kresoxim-methyl 8-hydroxyoctanoic acid 0.5980929 Likely
    98 Kresoxim-methyl dodecanoic acid 0.59499285 Likely
    99 Kresoxim-methyl 10-hydroxydecanoic acid 0.58491864 Likely
    100 Metrafenone 2-aminohexanoic acid 0.55733598 Likely
    101 Oxathiapiprolin 2-aminohexanoic acid 0.60657606 Likely
    102 Oxathiapiprolin 2-aminobutyric acid 0.57620296 Likely
    103 Oxathiapiprolin 2-hydroxybutyric acid 0.57121888 Likely
    104 Oxathiapiprolin 2-hydroxyhexanoic acid 0.56699662 Likely
    105 Oxathiapiprolin 2-hydroxyoctanoic acid 0.56303861 Likely
    106 Oxathiapiprolin 3-hydroxydecanoic acid 0.55268361 Likely
    107 Penflufen 2-aminohexanoic acid 0.65852257 Likely
    108 Penflufen 3-hydroxydecanoic acid 0.64106452 Likely
    109 Penflufen 2-aminobutyric acid 0.63676316 Likely
    110 Penflufen 2-hydroxyoctanoic acid 0.63645035 Likely
    111 Penflufen 3-hydroxyoctanoic acid 0.63215253 Likely
    112 Penflufen 2-hydroxyhexanoic acid 0.62836813 Likely
    113 Penflufen 2-hydroxybutyric acid 0.62790927 Likely
    114 Penflufen 8-hydroxyoctanoic acid 0.61006622 Likely
    115 Penflufen 3-aminobutyric acid 0.60708461 Likely
    116 Penflufen 3-hydroxyhexanoic acid 0.60651148 Likely
    117 Penflufen octanoic acid 0.60432406 Likely
    118 Penflufen nonanoic acid 0.59918836 Likely
    119 Penflufen heptanoic acid 0.59838795 Likely
    120 Penflufen 10-hydroxydecanoic acid 0.59837799 Likely
    121 Penflufen decanoic acid 0.59424908 Likely
    122 Penflufen 3-hydroxybutyric acid 0.59419846 Likely
    123 Penflufen hexanoic acid 0.59271353 Likely
    124 Penflufen dodecanoic acid 0.5846236 Likely
    125 Penthiopyrad 2-aminohexanoic acid 0.60944926 Likely
    126 Penthiopyrad 2-hydroxyoctanoic acid 0.59583883 Likely
    127 Penthiopyrad 3-hydroxydecanoic acid 0.59161762 Likely
    128 Penthiopyrad 2-hydroxyhexanoic acid 0.58502914 Likely
    129 Penthiopyrad 2-aminobutyric acid 0.58086249 Likely
    130 Penthiopyrad 3-hydroxyoctanoic acid 0.57843716 Likely
    131 Penthiopyrad 2-hydroxybutyric acid 0.57289048 Likely
    132 Penthiopyrad octanoic acid 0.56894523 Likely
    133 Penthiopyrad nonanoic acid 0.56465257 Likely
    134 Penthiopyrad heptanoic acid 0.56091047 Likely
    135 Penthiopyrad 8-hydroxyoctanoic acid 0.55971519 Likely
    136 Penthiopyrad decanoic acid 0.55588841 Likely
    137 Picoxystrobin 2-aminohexanoic acid 0.67534766 Likely
    138 Picoxystrobin 2-hydroxybutyric acid 0.6576197 Likely
    139 Picoxystrobin 2-aminobutyric acid 0.65465706 Likely
    140 Picoxystrobin 2-hydroxyhexanoic acid 0.65034573 Likely
    141 Picoxystrobin 2-hydroxyoctanoic acid 0.64606039 Likely
    142 Picoxystrobin 3-hydroxydecanoic acid 0.62761118 Likely
    143 Picoxystrobin 3-hydroxyoctanoic acid 0.62541364 Likely
    144 Picoxystrobin 3-hydroxyhexanoic acid 0.60288031 Likely
    145 Picoxystrobin 3-aminobutyric acid 0.60074316 Likely
    146 Picoxystrobin octanoic acid 0.59284889 Likely
    147 Picoxystrobin heptanoic acid 0.59142244 Likely
    148 Picoxystrobin 3-hydroxybutyric acid 0.5895552 Likely
    149 Picoxystrobin hexanoic acid 0.58764771 Likely
    150 Picoxystrobin nonanoic acid 0.58643743 Likely
    151 Picoxystrobin decanoic acid 0.58045772 Likely
    152 Picoxystrobin dodecanoic acid 0.56836147 Likely
    153 Picoxystrobin 8-hydroxyoctanoic acid 0.55987424 Likely
    154 Prothiaconazole 2-aminohexanoic acid 0.55020457 Likely
    155 Pydiflumetofen 2-aminohexanoic acid 0.59467448 Likely
    (Adepidyn)
    156 Pydiflumetofen 2-aminobutyric acid 0.56779618 Likely
    (Adepidyn)
    157 Pydiflumetofen 3-hydroxydecanoic acid 0.55150402 Likely
    (Adepidyn)
    158 Pydiflumetofen 2-hydroxyoctanoic acid 0.55106064 Likely
    (Adepidyn)
    159 Revysol 2-aminohexanoic acid 0.63962624 Likely
    160 Revysol 2-aminobutyric acid 0.6040647 Likely
    161 Revysol 2-hydroxyhexanoic acid 0.57211448 Likely
    162 Revysol 2-hydroxybutyric acid 0.57152455 Likely
    163 Revysol 2-hydroxyoctanoic acid 0.5706463 Likely
    164 Revysol 3-hydroxyoctanoic acid 0.5657302 Likely
    165 Revysol 3-hydroxydecanoic acid 0.56351714 Likely
    166 Revysol 3-aminobutyric acid 0.55580375 Likely
    167 Revysol octanoic acid 0.55272278 Likely
    168 Revysol decanoic acid 0.55074132 Likely
    169 Sedaxane 2-aminohexanoic acid 0.61273053 Likely
    170 Sedaxane 2-hydroxybutyric acid 0.60053037 Likely
    171 Sedaxane 2-aminobutyric acid 0.59536255 Likely
    172 Sedaxane 3-hydroxydecanoic acid 0.58749265 Likely
    173 Sedaxane 2-hydroxyhexanoic acid 0.58642283 Likely
    174 Sedaxane 2-hydroxyoctanoic acid 0.58351983 Likely
    175 Sedaxane 3-hydroxyoctanoic acid 0.58184892 Likely
    176 Sedaxane 3-aminobutyric acid 0.57278869 Likely
    177 Sedaxane 3-hydroxyhexanoic acid 0.56216563 Likely
    178 Sedaxane 3-hydroxybutyric acid 0.55541366 Likely
    179 Trifloxystrobin 2-hydroxyoctanoic acid 0.65884011 Likely
    180 Trifloxystrobin 2-hydroxyhexanoic acid 0.6587482 Likely
    181 Trifloxystrobin 2-aminobutyric acid 0.65764501 Likely
    182 Trifloxystrobin 2-hydroxybutyric acid 0.65679943 Likely
    183 Trifloxystrobin 3-hydroxydecanoic acid 0.64921461 Likely
    184 Trifloxystrobin 3-hydroxyoctanoic acid 0.64454011 Likely
    185 Trifloxystrobin 3-hydroxyhexanoic acid 0.62748345 Likely
    186 Trifloxystrobin 3-aminobutyric acid 0.62415011 Likely
    187 Trifloxystrobin octanoic acid 0.6218323 Likely
    188 Trifloxystrobin heptanoic acid 0.62072241 Likely
    189 Trifloxystrobin hexanoic acid 0.61619104 Likely
    190 Trifloxystrobin nonanoic acid 0.61475129 Likely
    191 Trifloxystrobin 3-hydroxybutyric acid 0.61418406 Likely
    192 Trifloxystrobin decanoic acid 0.60804051 Likely
    193 Trifloxystrobin dodecanoic acid 0.59491928 Likely
    194 Trifloxystrobin 8-hydroxyoctanoic acid 0.59290993 Likely
    195 Trifloxystrobin 10-hydroxydecanoic acid 0.57914078 Likely
    196 Valifenalate 2-aminohexanoic acid 0.5944192 Likely
    197 Valifenalate 2-aminobutyric acid 0.56510459 Likely
    198 Valifenalate 2-hydroxyoctanoic acid 0.55897016 Likely
    199 Valifenalate 3-hydroxydecanoic acid 0.55603569 Likely
  • Example 25: Predicted synergistic efficacy for in vitro growth inhibition of Sclerotinia sclerotiorum by bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, penflufen, penthiopyrad, picoxystrobin, pydiflumetofen, revysol, trifloxystrobin, and valifenalate, in combination with various exemplary saturated and unsaturated C4-C12 aliphatic acids, according to an embodiment of the present disclosure.
  • A prediction of probability of synergistic efficacy for each combination of bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, penflufen, penthiopyrad, picoxystrobin, pydiflumetofen, revysol, trifloxystrobin, and valifenalate (Compound A) and saturated or unsaturated aliphatic acid (Compound B) compound was determined using a synergistic composition predictive model trained using an experimental in vitro synergistic efficacy dataset for in vitro growth inhibition of Sclerotinia sclerotiorum. The resulting synergistic efficacy predictions are shown in Table 90 below.
  • TABLE 90
    Predicted synergistic efficacy for in vitro growth inhibition of Sclerotinia sclerotiorum
    by bixafen, boscalid, fenpicoxamid, fenpyrazimine, florylpicoxamid, fluxapyroxad,
    isotianil, kresoxim-methyl, metrafenone, oxathiapiprolin, penflufen, penthiopyrad,
    picoxystrobin, prothioconazole, pydiflumetofen, revysol, sedaxane, trifloxystrobin,
    and valifenalate, in combination with various exemplary C4-C12 saturated and unsaturated
    aliphatic acids according to an embodiment of the present disclosure
    Predicted
    Probability of Synergistic
    Synergistic Efficacy
    Combination Compound A Compound B Efficacy Prediction
    1 Bixafen trans-2-nonenoic acid 0.63422002 Likely
    2 Bixafen trans-2-undecenoic acid 0.61975961 Likely
    3 Bixafen trans-2-decenoic acid 0.61877499 Likely
    4 Bixafen trans-2-octenoic acid 0.59647564 Likely
    5 Bixafen 3-decenoic acid 0.56026628 Likely
    6 Boscalid trans-2-undecenoic acid 0.64000795 Likely
    7 Boscalid trans-2-decenoic acid 0.63932319 Likely
    8 Boscalid trans-2-nonenoic acid 0.63189319 Likely
    9 Boscalid trans-2-octenoic acid 0.6128523 Likely
    10 Boscalid 3-decenoic acid 0.56328052 Likely
    11 Boscalid dodecanoic acid 0.5582064 Likely
    12 Boscalid decanoic acid 0.5560983 Likely
    13 Boscalid nonanoic acid 0.55505839 Likely
    14 Boscalid octanoic acid 0.55438775 Likely
    15 Boscalid 3-nonenoic acid 0.55383059 Likely
    16 Fenpicoxamid trans-2-undecenoic acid 0.64517585 Likely
    17 Fenpicoxamid trans-2-decenoic acid 0.64430379 Likely
    18 Fenpicoxamid trans-2-nonenoic acid 0.63685218 Likely
    19 Fenpicoxamid trans-2-octenoic acid 0.61571277 Likely
    20 Fenpicoxamid 3-decenoic acid 0.5717719 Likely
    21 Fenpicoxamid dodecanoic acid 0.56812335 Likely
    22 Fenpicoxamid decanoic acid 0.56706998 Likely
    23 Fenpicoxamid nonanoic acid 0.5660589 Likely
    24 Fenpicoxamid octanoic acid 0.56546112 Likely
    25 Fenpicoxamid heptanoic acid 0.56213194 Likely
    26 Fenpicoxamid 3-nonenoic acid 0.56106859 Likely
    27 Fenpyrazamine trans-2-undecenoic acid 0.64570129 Likely
    28 Fenpyrazamine trans-2-decenoic acid 0.64445113 Likely
    29 Fenpyrazamine trans-2-nonenoic acid 0.64373701 Likely
    30 Fenpyrazamine trans-2-octenoic acid 0.61870502 Likely
    31 Fenpyrazamine 3-decenoic acid 0.57072864 Likely
    32 Fenpyrazamine dodecanoic acid 0.56926688 Likely
    33 Fenpyrazamine decanoic acid 0.56696534 Likely
    34 Fenpyrazamine nonanoic acid 0.56557274 Likely
    35 Fenpyrazamine octanoic acid 0.56470615 Likely
    36 Fenpyrazamine 3-nonenoic acid 0.56308404 Likely
    37 Fenpyrazamine heptanoic acid 0.56026874 Likely
    38 Fenpyrazamine trans-2-hexenoic acid 0.55896424 Likely
    39 Fenpyrazamine 9-decenoic acid 0.55287297 Likely
    40 Florylpicoxamid trans-2-undecenoic acid 0.66003401 Likely
    41 Florylpicoxamid trans-2-decenoic acid 0.65861813 Likely
    42 Florylpicoxamid trans-2-nonenoic acid 0.65382792 Likely
    43 Florylpicoxamid trans-2-octenoic acid 0.63490106 Likely
    44 Florylpicoxamid 3-decenoic acid 0.58621619 Likely
    45 Florylpicoxamid dodecanoic acid 0.5781119 Likely
    46 Florylpicoxamid 3-nonenoic acid 0.57620949 Likely
    47 Florylpicoxamid trans-2-hexenoic acid 0.57501872 Likely
    48 Florylpicoxamid nonanoic acid 0.57407232 Likely
    49 Florylpicoxamid decanoic acid 0.5728504 Likely
    50 Florylpicoxamid octanoic acid 0.5696201 Likely
    51 Florylpicoxamid heptanoic acid 0.56792373 Likely
    52 Florylpicoxamid 3-octenoic acid 0.55302533 Likely
    53 Florylpicoxamid hexanoic acid 0.55097026 Likely
    54 Fluxapyroxad trans-2-undecenoic acid 0.66353832 Likely
    55 Fluxapyroxad trans-2-decenoic acid 0.66228828 Likely
    56 Fluxapyroxad trans-2-nonenoic acid 0.65719566 Likely
    57 Fluxapyroxad trans-2-octenoic acid 0.63807777 Likely
    58 Fluxapyroxad 3-decenoic acid 0.58704056 Likely
    59 Fluxapyroxad 3-nonenoic acid 0.57704323 Likely
    60 Fluxapyroxad trans-2-hexenoic acid 0.56795649 Likely
    61 Fluxapyroxad dodecanoic acid 0.56294662 Likely
    62 Fluxapyroxad decanoic acid 0.56026234 Likely
    63 Fluxapyroxad nonanoic acid 0.55851251 Likely
    64 Fluxapyroxad octanoic acid 0.55714217 Likely
    65 Fluxapyroxad 3-octenoic acid 0.55502918 Likely
    66 Fluxapyroxad trans-3-octenoic acid 0.55502918 Likely
    67 Fluxapyroxad heptanoic acid 0.5533742 Likely
    68 Isotianil trans-2-undecenoic acid 0.58734897 Likely
    69 Isotianil trans-2-decenoic acid 0.5861208 Likely
    70 Isotianil trans-2-nonenoic acid 0.57581536 Likely
    71 Isotianil trans-2-octenoic acid 0.55436011 Likely
    72 Kresoxim-methyl trans-2-undecenoic acid 0.69437059 Likely
    73 Kresoxim-methyl trans-2-nonenoic acid 0.68996981 Likely
    74 Kresoxim-methyl trans-2-decenoic acid 0.68445944 Likely
    75 Kresoxim-methyl trans-2-octenoic acid 0.67452894 Likely
    76 Kresoxim-methyl dodecanoic acid 0.63170701 Likely
    77 Kresoxim-methyl 3-decenoic acid 0.62730097 Likely
    78 Kresoxim-methyl nonanoic acid 0.62720372 Likely
    79 Kresoxim-methyl decanoic acid 0.62517832 Likely
    80 Kresoxim-methyl octanoic acid 0.62229298 Likely
    81 Kresoxim-methyl heptanoic acid 0.61779979 Likely
    82 Kresoxim-methyl 3-nonenoic acid 0.61715368 Likely
    83 Kresoxim-methyl trans-2-hexenoic acid 0.616918 Likely
    84 Kresoxim-methyl hexanoic acid 0.59974539 Likely
    85 Kresoxim-methyl 3-octenoic acid 0.59338092 Likely
    86 Kresoxim-methyl 9-decenoic acid 0.58882145 Likely
    87 Kresoxim-methyl 3-heptenoic acid 0.5842284 Likely
    88 Kresoxim-methyl trans-3-octenoic acid 0.58338154 Likely
    89 Kresoxim-methyl 2-ethylhexanoic acid 0.58021401 Likely
    90 Kresoxim-methyl 3-methylnonanoic acid 0.57904676 Likely
    91 Kresoxim-methyl 2-methyloctanoic acid 0.57545126 Likely
    92 Kresoxim-methyl 2-methyldecanoic acid 0.57396175 Likely
    93 Kresoxim-methyl 7-octenoic acid 0.56941623 Likely
    94 Kresoxim-methyl 2-hydroxyoctanoic acid 0.56689941 Likely
    95 Kresoxim-methyl 2-aminohexanoic acid 0.56447951 Likely
    96 Metrafenone trans-2-undecenoic acid 0.64443278 Likely
    97 Metrafenone trans-2-decenoic acid 0.64366354 Likely
    98 Metrafenone trans-2-nonenoic acid 0.63731814 Likely
    99 Metrafenone trans-2-octenoic acid 0.61913326 Likely
    100 Metrafenone 3-decenoic acid 0.56409456 Likely
    101 Metrafenone dodecanoic acid 0.55737829 Likely
    102 Metrafenone trans-2-hexenoic acid 0.55535108 Likely
    103 Metrafenone 3-nonenoic acid 0.55484796 Likely
    104 Metrafenone decanoic acid 0.55289211 Likely
    105 Metrafenone nonanoic acid 0.55017602 Likely
    106 Penflufen trans-2-undecenoic acid 0.64399335 Likely
    107 Penflufen trans-2-decenoic acid 0.64252008 Likely
    108 Penflufen trans-2-nonenoic acid 0.62746654 Likely
    109 Penflufen trans-2-octenoic acid 0.61407125 Likely
    110 Penflufen dodecanoic acid 0.57058068 Likely
    111 Penflufen decanoic acid 0.56765798 Likely
    112 Penflufen nonanoic acid 0.56592093 Likely
    113 Penflufen octanoic acid 0.56437438 Likely
    114 Penflufen 3-decenoic acid 0.56411505 Likely
    115 Penflufen 3-nonenoic acid 0.56120105 Likely
    116 Penflufen heptanoic acid 0.55998814 Likely
    117 Penthiopyrad trans-2-decenoic acid 0.60351946 Likely
    118 Penthiopyrad trans-2-octenoic acid 0.57867577 Likely
    119 Picoxystrobin trans-2-decenoic acid 0.6041138 Likely
    120 Picoxystrobin trans-2-undecenoic acid 0.60380391 Likely
    121 Picoxystrobin trans-2-nonenoic acid 0.60102845 Likely
    122 Picoxystrobin trans-2-octenoic acid 0.58557471 Likely
    123 Pydiflumetofen (Adepidyn) trans-2-undecenoic acid 0.62980278 Likely
    124 Pydiflumetofen (Adepidyn) trans-2-decenoic acid 0.62913683 Likely
    125 Pydiflumetofen (Adepidyn) trans-2-nonenoic acid 0.6215863 Likely
    126 Pydiflumetofen (Adepidyn) trans-2-octenoic acid 0.59947248 Likely
    127 Pydiflumetofen (Adepidyn) dodecanoic acid 0.55658742 Likely
    128 Pydiflumetofen (Adepidyn) decanoic acid 0.55425756 Likely
    129 Pydiflumetofen (Adepidyn) nonanoic acid 0.55224037 Likely
    130 Pydiflumetofen (Adepidyn) octanoic acid 0.55034847 Likely
    131 Revysol trans-2-undecenoic acid 0.57872331 Likely
    132 Revysol trans-2-decenoic acid 0.57789835 Likely
    133 Revysol trans-2-nonenoic acid 0.57143113 Likely
    134 Revysol trans-2-octenoic acid 0.55187153 Likely
    135 Trifloxystrobin trans-2-octenoic acid 0.65344118 Likely
    136 Trifloxystrobin dodecanoic acid 0.60296979 Likely
    137 Trifloxystrobin 3-decenoic acid 0.60065202 Likely
    138 Trifloxystrobin decanoic acid 0.59917673 Likely
    139 Trifloxystrobin nonanoic acid 0.59665176 Likely
    140 Trifloxystrobin octanoic acid 0.59411821 Likely
    141 Trifloxystrobin trans-2-hexenoic acid 0.58938381 Likely
    142 Trifloxystrobin 3-nonenoic acid 0.58652177 Likely
    143 Trifloxystrobin heptanoic acid 0.58451477 Likely
    144 Trifloxystrobin 3-octenoic acid 0.56976633 Likely
    145 Trifloxystrobin 9-decenoic acid 0.56827708 Likely
    146 Trifloxystrobin trans-3-octenoic acid 0.56589124 Likely
    147 Trifloxystrobin hexanoic acid 0.56398016 Likely
    148 Trifloxystrobin 3-heptenoic acid 0.56110153 Likely
    149 Trifloxystrobin 3-methylnonanoic acid 0.55144026 Likely
    150 Valifenalate trans-2-octenoic acid 0.62518207 Likely
    151 Valifenalate 3-decenoic acid 0.57403389 Likely
    152 Valifenalate trans-2-hexenoic acid 0.57030915 Likely
    153 Valifenalate nonanoic acid 0.5635556 Likely
    154 Valifenalate dodecanoic acid 0.56304971 Likely
    155 Valifenalate decanoic acid 0.55918886 Likely
    156 Valifenalate octanoic acid 0.55868943 Likely
    157 Valifenalate heptanoic acid 0.55620831 Likely
    158 Valifenalate 3-nonenoic acid 0.55386801 Likely
  • Example 26: Predicted synergistic efficacy for in vitro growth inhibition of Botritis cinerea by bixafen, fenpicoxamid, florylpicoxamid, fluxapyroxad, kresoxim-methyl, picoxystrobin, pydiflumetofen, revysol, trifloxystrobin, and valifenalate, in combination with various exemplary saturated and unsaturated C4-C12 aliphatic acids, according to an embodiment of the present disclosure.
  • A prediction of probability of synergistic efficacy for each combination of bixafen, fenpicoxamid, florylpicoxamid, fluxapyroxad, kresoxim-methyl, picoxystrobin, pydiflumetofen, revysol, trifloxystrobin, and valifenalate (Compound A) and a saturated or unsaturated C4-C12 aliphatic acid (Compound B) compound was determined using a synergistic composition predictive model trained using an experimental in vitro synergistic efficacy dataset for in vitro growth inhibition ofBotritis cinerea. The resulting synergistic efficacy predictions are shown in Table 91 below.
  • TABLE 91
    Predicted synergistic efficacy for in vitro growth inhibition of Botritis cinerea
    by bixafen, fenpicoxamid, florylpicoxamid, fluxapyroxad, kresoxim-methyl, picoxystrobin,
    pydiflumetofen, revysol, trifloxystrobin, and valifenalate, in combination with
    various exemplary saturated and unsaturated C4-C12 aliphatic acids
    Predicted
    Probability of Synergistic
    Synergistic Efficacy
    Combination Compound A Compound B Efficacy Prediction
    1 Bixafen 9-decenoic acid 0.55622956 Likely
    2 Bixafen decanoic acid 0.55589771 Likely
    3 Bixafen octanoic acid 0.55586089 Likely
    4 Bixafen nonanoic acid 0.55584134 Likely
    5 Bixafen dodecanoic acid 0.55552297 Likely
    6 Fenpicoxamid nonanoic acid 0.62459222 Likely
    7 Fenpicoxamid octanoic acid 0.61360456 Likely
    8 Fenpicoxamid decanoic acid 0.61240222 Likely
    9 Fenpicoxamid dodecanoic acid 0.61135991 Likely
    10 Fenpicoxamid heptanoic acid 0.61086404 Likely
    11 Fenpicoxamid 9-decenoic acid 0.60419807 Likely
    12 Fenpicoxamid 7-octenoic acid 0.58622763 Likely
    13 Fenpicoxamid hexanoic acid 0.58429749 Likely
    14 Fenpicoxamid 8-hydroxyoctanoic acid 0.57570006 Likely
    15 Fenpicoxamid 10-hydroxydecanoic acid 0.57503872 Likely
    16 Fenpicoxamid 12-hydroxydodecanoic acid 0.57498789 Likely
    17 Fenpicoxamid 3-methylnonanoic acid 0.55528876 Likely
    18 Fenpicoxamid 5-hexenoic acid 0.55508957 Likely
    19 Florylpicoxamid decanoic acid 0.71071466 Likely
    20 Florylpicoxamid nonanoic acid 0.71019579 Likely
    21 Florylpicoxamid dodecanoic acid 0.70658516 Likely
    22 Florylpicoxamid octanoic acid 0.70647826 Likely
    23 Florylpicoxamid heptanoic acid 0.6966848 Likely
    24 Florylpicoxamid 9-decenoic acid 0.69075607 Likely
    25 Florylpicoxamid 8-hydroxyoctanoic acid 0.68890783 Likely
    26 Florylpicoxamid 12-hydroxydodecanoic acid 0.68347669 Likely
    27 Florylpicoxamid 10-hydroxydecanoic acid 0.6833026 Likely
    28 Florylpicoxamid 7-octenoic acid 0.68061823 Likely
    29 Florylpicoxamid hexanoic acid 0.68034807 Likely
    30 Florylpicoxamid 5-hexenoic acid 0.63863994 Likely
    31 Florylpicoxamid 3-methylnonanoic acid 0.63745326 Likely
    32 Florylpicoxamid trans-2-undecenoic acid 0.63357106 Likely
    33 Florylpicoxamid trans-2-decenoic acid 0.62787411 Likely
    34 Florylpicoxamid 3-decenoic acid 0.61742779 Likely
    35 Florylpicoxamid trans-2-nonenoic acid 0.61304636 Likely
    36 Florylpicoxamid 3-nonenoic acid 0.6103797 Likely
    37 Florylpicoxamid 3-methylhexanoic acid 0.60093858 Likely
    38 Florylpicoxamid 3-heptenoic acid 0.5967274 Likely
    39 Florylpicoxamid trans-2-octenoic acid 0.59637633 Likely
    40 Florylpicoxamid 3-octenoic acid 0.59633581 Likely
    41 Florylpicoxamid trans-3-octenoic acid 0.59633581 Likely
    42 Florylpicoxamid trans-2-hexenoic acid 0.57528369 Likely
    43 Florylpicoxamid trans-3-hexenoic acid 0.56214715 Likely
    44 Florylpicoxamid cis-3-hexenoic acid 0.56185557 Likely
    45 Florylpicoxamid 4-hexenoic acid 0.55965197 Likely
    46 Florylpicoxamid 2-methyloctanoic acid 0.55344194 Likely
    47 Florylpicoxamid 2-methyldecanoic acid 0.55045301 Likely
    48 Florylpicoxamid 3-methylbutyric acid 0.55003294 Likely
    49 Fluxapyroxad 9-decenoic acid 0.57082343 Likely
    50 Fluxapyroxad decanoic acid 0.5582246 Likely
    51 Fluxapyroxad dodecanoic acid 0.55812293 Likely
    52 Fluxapyroxad octanoic acid 0.55790607 Likely
    53 Kresoxim-methyl 9-decenoic acid 0.65007721 Likely
    54 Kresoxim-methyl dodecanoic acid 0.64561872 Likely
    55 Kresoxim-methyl decanoic acid 0.64533766 Likely
    56 Kresoxim-methyl octanoic acid 0.64519368 Likely
    57 Kresoxim-methyl nonanoic acid 0.64517309 Likely
    58 Kresoxim-methyl heptanoic acid 0.63135262 Likely
    59 Kresoxim-methyl 7-octenoic acid 0.63015161 Likely
    60 Kresoxim-methyl 8-hydroxyoctanoic acid 0.62234793 Likely
    61 Kresoxim-methyl 12-hydroxydodecanoic acid 0.62204227 Likely
    62 Kresoxim-methyl 10-hydroxydecanoic acid 0.62185931 Likely
    63 Kresoxim-methyl hexanoic acid 0.61156485 Likely
    64 Kresoxim-methyl 5-hexenoic acid 0.58608413 Likely
    65 Kresoxim-methyl 3-methylnonanoic acid 0.58495826 Likely
    66 Kresoxim-methyl trans-2-decenoic acid 0.5617413 Likely
    67 Kresoxim-methyl trans-2-undecenoic acid 0.5611554 Likely
    68 Kresoxim-methyl 3-decenoic acid 0.55813311 Likely
    69 Picoxystrobin 9-decenoic acid 0.64360938 Likely
    70 Picoxystrobin decanoic acid 0.63400232 Likely
    71 Picoxystrobin nonanoic acid 0.6337739 Likely
    72 Picoxystrobin octanoic acid 0.63365494 Likely
    73 Picoxystrobin dodecanoic acid 0.63256371 Likely
    74 Picoxystrobin 7-octenoic acid 0.62759129 Likely
    75 Picoxystrobin heptanoic acid 0.62253746 Likely
    76 Picoxystrobin 12-hydroxydodecanoic acid 0.61545208 Likely
    77 Picoxystrobin 8-hydroxyoctanoic acid 0.61335731 Likely
    78 Picoxystrobin 10-hydroxydecanoic acid 0.60911996 Likely
    79 Picoxystrobin hexanoic acid 0.60391683 Likely
    80 Picoxystrobin 5-hexenoic acid 0.58423756 Likely
    81 Picoxystrobin trans-2-decenoic acid 0.57715665 Likely
    82 Picoxystrobin trans-2-undecenoic acid 0.57706139 Likely
    83 Picoxystrobin 3-decenoic acid 0.56894624 Likely
    84 Picoxystrobin trans-2-nonenoic acid 0.56590575 Likely
    85 Picoxystrobin 3-nonenoic acid 0.56021643 Likely
    86 Picoxystrobin 3-methylnonanoic acid 0.55981524 Likely
    87 Picoxystrobin trans-2-octenoic acid 0.55049884 Likely
    88 Pydiflumetofen (Adepidyn) octanoic acid 0.58507421 Likely
    89 Pydiflumetofen (Adepidyn) nonanoic acid 0.58455386 Likely
    90 Pydiflumetofen (Adepidyn) decanoic acid 0.58388714 Likely
    91 Pydiflumetofen (Adepidyn) dodecanoic acid 0.58166713 Likely
    92 Pydiflumetofen (Adepidyn) heptanoic acid 0.57342989 Likely
    93 Pydiflumetofen (Adepidyn) 9-decenoic acid 0.57237365 Likely
    94 Pydiflumetofen (Adepidyn) hexanoic acid 0.55570532 Likely
    95 Pydiflumetofen (Adepidyn) 7-octenoic acid 0.55530685 Likely
    96 Revysol dodecanoic acid 0.6001254 Likely
    97 Revysol decanoic acid 0.59978312 Likely
    98 Revysol nonanoic acid 0.59915221 Likely
    99 Revysol octanoic acid 0.59870726 Likely
    100 Revysol heptanoic acid 0.5884472 Likely
    101 Revysol 9-decenoic acid 0.58379308 Likely
    102 Revysol hexanoic acid 0.56996538 Likely
    103 Revysol 7-octenoic acid 0.56562299 Likely
    104 Revysol 12-hydroxydodecanoic acid 0.56383193 Likely
    105 Revysol 10-hydroxydecanoic acid 0.56139958 Likely
    106 Revysol 8-hydroxyoctanoic acid 0.55953437 Likely
    107 Revysol 3-methylnonanoic acid 0.5520322 Likely
    108 Trifloxystrobin 9-decenoic acid 0.6725654 Likely
    109 Trifloxystrobin dodecanoic acid 0.66157781 Likely
    110 Trifloxystrobin decanoic acid 0.66133578 Likely
    111 Trifloxystrobin nonanoic acid 0.66097871 Likely
    112 Trifloxystrobin octanoic acid 0.66093915 Likely
    113 Trifloxystrobin 7-octenoic acid 0.65512001 Likely
    114 Trifloxystrobin heptanoic acid 0.65001921 Likely
    115 Trifloxystrobin 12-hydroxydodecanoic acid 0.64941725 Likely
    116 Trifloxystrobin 10-hydroxydecanoic acid 0.64885914 Likely
    117 Trifloxystrobin 8-hydroxyoctanoic acid 0.64848276 Likely
    118 Trifloxystrobin hexanoic acid 0.63310591 Likely
    119 Trifloxystrobin 3-methylnonanoic acid 0.61211242 Likely
    120 Trifloxystrobin 5-hexenoic acid 0.60404247 Likely
    121 Trifloxystrobin trans-2-decenoic acid 0.59111476 Likely
    122 Trifloxystrobin trans-2-undecenoic acid 0.59108112 Likely
    123 Trifloxystrobin 3-decenoic acid 0.58504908 Likely
    124 Trifloxystrobin trans-2-nonenoic acid 0.57766945 Likely
    125 Trifloxystrobin 3-nonenoic acid 0.57481307 Likely
    126 Trifloxystrobin 3-methylhexanoic acid 0.57295034 Likely
    127 Trifloxystrobin trans-2-octenoic acid 0.56120624 Likely
    128 Trifloxystrobin 3-octenoic acid 0.56061667 Likely
    129 Trifloxystrobin 3-heptenoic acid 0.5584203 Likely
    130 Valifenalate dodecanoic acid 0.59915539 Likely
    131 Valifenalate decanoic acid 0.5985593 Likely
    132 Valifenalate nonanoic acid 0.59810962 Likely
    133 Valifenalate octanoic acid 0.59787693 Likely
    134 Valifenalate heptanoic acid 0.58391599 Likely
    135 Valifenalate 9-decenoic acid 0.58095987 Likely
    136 Valifenalate hexanoic acid 0.56507724 Likely
    137 Valifenalate 12-hydroxydodecanoic acid 0.5648372 Likely
    138 Valifenalate 10-hydroxydecanoic acid 0.56308371 Likely
    139 Valifenalate 8-hydroxyoctanoic acid 0.56188978 Likely
    140 Valifenalate 7-octenoic acid 0.56071382 Likely
  • In some embodiments according to the present disclosure, and as illustrated in some exemplary embodiments in the above-described experimental examples, the combination of a C4-C10 unsaturated aliphatic acid (and agriculturally acceptable salts thereof in some particular embodiments) and a pesticidal active ingredient produces a synergistic pesticidal composition demonstrating or reasonably predicted to demonstrate a synergistic effect. That is, when used in combination, the C4-C10 unsaturated aliphatic acid and the pesticidal active ingredient have or are reasonably predicted to have an efficacy that is greater than would be expected by simply adding the efficacy of the pesticidal active ingredient and the C4-C10 unsaturated aliphatic acid when used alone. In some alternative embodiments, the unsaturated aliphatic acid or agriculturally acceptable salt thereof may comprise a C11 unsaturated aliphatic acid or agriculturally acceptable salt thereof. In some further alternative embodiments, the unsaturated aliphatic acid or agriculturally acceptable salt thereof may comprise a C12 unsaturated aliphatic acid or agriculturally acceptable salt thereof.
  • In some embodiments according to the present disclosure, and as illustrated in some exemplary embodiments in the above-described experimental examples, the combination of a C4-C10 saturated aliphatic acid (and agriculturally acceptable salts thereof in some particular embodiments) and a pesticidal active ingredient produces a synergistic pesticidal composition demonstrating a synergistic effect or reasonably predicted to demonstrate a synergistic effect. That is, when used in combination, the C4-C10 saturated aliphatic acid and the pesticidal active ingredient have or are predicted to have an efficacy that is greater than would be expected by simply adding the efficacy of the pesticidal active ingredient and the C4-C10 saturated aliphatic acid when used alone. In some particular embodiments, the combination of a C4-C10 saturated aliphatic acid and a neem seed, kernel, oil, extract or derivative pesticidal active ingredient produces a synergistic pesticidal composition demonstrating a synergistic pesticidal effect. In some further embodiments, the combination of a C11 or C12 saturated aliphatic acid and a neem seed, kernel, oil, extract or derivative pesticidal active ingredient produces a synergistic pesticidal composition demonstrating or reasonably predicted to demonstrate a synergistic pesticidal effect. In some alternative embodiments according to the present disclosure, the combination of a C11 or C12 saturated aliphatic acid (and agriculturally acceptable salts thereof in some particular embodiments) and a pesticidal active ingredient produces a synergistic pesticidal composition demonstrating a synergistic effect.
  • While a number of exemplary aspects and embodiments have been discussed above, those of skill in the art will recognize certain modifications, permutations, additions and sub-combinations thereof. It is therefore intended that the following appended claims and claims hereafter introduced are to be given the broadest interpretation consistent with the disclosure as a whole.

Claims (28)

1. A synergistic pesticidal composition comprising
a pesticidal active ingredient selected from the list comprising: benzovindiflupyr, bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, oxathiapiprolin, penflufen, penthiopyrad, picoxystrobin, prothioconazole, pydiflumetofen, revysol, sedaxane, trifloxystrobin, pyraclostrobin, azoxystrobin, chlorothalonil, cyprodinil, metalaxyl, epoxiconazole, propiconazole, difenoconazole, fludioxonil, mancozeb, tebuconazole, valifenalate, and combinations thereof; and
a C4-C10 saturated or unsaturated aliphatic acid or an agriculturally compatible salt thereof;
wherein a ratio of the concentrations of said pesticidal active ingredient and said C4-C10 saturated or unsaturated aliphatic acid or an agriculturally compatible salt thereof is between about 1:15000 and 15000:1.
2. The synergistic pesticidal composition according to claim 1, wherein said C4-C10 saturated or unsaturated aliphatic acid comprises a C4-C10 unsaturated aliphatic acid;
wherein the C4-C10 unsaturated aliphatic acid comprises at least one unsaturated C—C bond; and
wherein a ratio of the concentrations of said pesticidal active ingredient and said C4-C10 unsaturated aliphatic acid is between about 1:15,000 and 15,000:1.
3. (canceled)
4. The synergistic pesticidal composition according to claim 1, wherein the C4-C10 saturated or unsaturated aliphatic acid or salt thereof comprises a methyl-, ethyl-, hydroxy-, or amino-substituent.
5. The synergistic pesticidal composition according to claim 2, wherein the C4-C10 unsaturated aliphatic acid comprises at least one of:
a trans-butanoic acid, a cis-butanoic acid, a butynoic acid, a buta-dienoic acid, a trans-hexenoic acid, a cis-hexenoic acid, a hexa-dienoic acid, a hexynoic acid, a trans-heptenoic acid, a cis-heptenoic acid, a hepta-dienoic acid, a heptynoic acid, a trans-octenoic acid, a cis-octenoic acid, an octa-dienoic acid, an octynoic acid, a trans-nonenoic acid, a cis-nonenoic acid, a nona-dienoic acid, a nonynoic acid, a trans-decenoic acid, a cis-decenoic acid, a deca-dienoic acid, and a decynoic acid.
6. (canceled)
7. (canceled)
8. The synergistic pesticidal composition according to claim 1, wherein the synergistic pesticidal composition has a predicted probability of synergy of greater than 0.55.
9.-11. (canceled)
12. The synergistic pesticidal composition according to claim 1, wherein said pesticidal active ingredient comprises at least one pesticidal active ingredient selected from the list comprising:
A) Respiration inhibitors selected from:
inhibitors of complex III at Qo site: azoxystrobin (II-1), coumethoxy-strobin, coumoxystrobin, dimoxystrobin (II-2), enestroburin, fenamin-strobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin (II-3), kresoxim-methyl (II-4), metominostrobin, orysastrobin (II-5), picoxystrobin (II-6), pyraclostrobin (II-7), pyrametostrobin, pyraoxystrobin, trifloxystrobin (II-8), 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneamino-oxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, fenamidone;
Inhibitors of complex III at Qi site: cyazofamid, amisulbrom, [(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)-amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbony-loxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol5-ylmethoxy)-4-methoxy-pyridine-2-carbon-yl]amino]-6-methyl-4,9-dioxol,5-dioxonan-7-yl] 2-methylpropanoate; (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenyl-methyl)-1,5-dioxonan-7-yl 2-methylpropanoate;
Inhibitors of complex II: benodanil, benzovindiflupyr (II-9), bixafen (II-10), boscalid (II-11), carboxin, fenfuram, fluopyram (II-12), flutolanil, fluxapyroxad (II-13), furametpyr, isofetamid, isopyrazam (II-14), mepronil, oxycarboxin, penflufen (II-15), penthiopyrad (II-16), sedaxane (II-17), tecloftalam, thifluzamide, N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide, 3-(difluorome-thyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, N-(7-fluoro-1,1,3-trime-thyl-indan-4-yl)-1,3-dimethyl-pyrazole-4-carboxamide, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide;
Other respiration inhibitors: diflumetorim, (5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluorometh-ylpyridin-2-yloxy)-phenyl]-ethyl}-amine; binapacryl, dinobuton, dinocap, fluazinam (II-18); ferimzone; fentin salts such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin (II-19); and silthiofam; B) Sterol biosynthesis inhibitors (SBI fungicides) selected from:
C14 demethylase inhibitors (DMI fungicides): azaconazole, bitertanol, bromuconazole, cyproconazole (II-20), difenoconazole (II-21), diniconazole, diniconazole-M, epoxiconazole (II-22), fenbuconazole, fluquinconazole (II-23), flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole (II-24), myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole (II-25), prothioconazole (II-26), simeconazole, tebuconazole (II-27), tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole; imazalil, pefurazoate, prochloraz, triflumizol; fenarimol, nuarimol, pyrifenox, triforine, [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol;
Delta14-reductase inhibitors: aldimorph, dodemorph, dodemorphacetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
Inhibitors of 3-keto reductase: fenhexamid;
C) Nucleic acid synthesis inhibitors selected from:
phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam) (II-38), ofurace, oxadixyl;
others nucleic acid inhibitors: hymexazole, octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;
D) Inhibitors of cell division and cytoskeleton selected from:
tubulin inhibitors: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl (II-39); 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine
other cell division inhibitors: diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone (II-40), pyriofenone;
E) Inhibitors of amino acid and protein synthesis selected from:
methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil, mepanipyrim, Pyrimethanil (II-41);
protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
F) Signal transduction inhibitors selected from:
MAP/histidine kinase inhibitors: fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
G protein inhibitors: quinoxyfen;
G) Lipid and membrane synthesis inhibitors selected from:
Phospholipid biosynthesis inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; propamocarb, propamocarb-hydrochloride;
lipid peroxidation inhibitors: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
phospholipid biosynthesis and cell wall deposition: dimethomorph (II-42), flumorph, mandipropamid (II-43), pyrimorph, benthiavalicarb, iprovalicarb, valifenalate, N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
acid amide hydrolase inhibitors: oxathiapiprolin;
H) Inhibitors with Multi Site Action selected from:
 inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride (II-44), basic copper sulfate, sulfur;
thio- and dithiocarbamates: ferbam, mancozeb (II-45), maneb, metam, metiram (II-46), propineb, thiram, zineb, ziram;
organochlorine compounds: anilazine, Chlorothalonil (II-47), captafol, captan, folpet, dichlofluanid, dichlorophen, hexachlorobenzene, pentachlorophenole and its salts, phthalide, tolylfluanid, N-(4-chlo-ro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
guanidines and others: guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoc-tadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon, 2,6-dimethyl-1H,5H-[1,4]dithii-no[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone (II-48);
I) Cell wall synthesis inhibitors selected from:
inhibitors of glucan synthesis: validamycin, polyoxin B;
melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamid, dicyclomet, fenoxanil;
J) Plant defence inducers selected from:
acibenzolar-S-methyl, probenazole, isotianil, tiadinil, prohexadione-calcium; fosetyl, fosetyl-aluminum, phosphorous acid and its salts (II-49);
K) Unknown mode of action selected from: bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover, flusulfamide, flutianil, methasulfocarb, nitrapyrin, nitrothal-isopropyl, oxathiapiprolin, tolprocarb, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, 2-[3,5-bis-(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yl-oxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]-ethanone, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen-4-one, N-(cyclo-propylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methyl formamidine, N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, methoxyacetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester, 3-[5-(4-meth-ylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole), N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide, 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole, 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phe-nyl)-isoxazol-5-yl]-2-prop2-ynyloxy-acetamide, ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate, tertbutyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]-amino]oxymethyl]-2-pyridyl]carbamate, pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, 2-[2-[(7,8-dif-luoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-qui-nolyl)oxy]phenyl]propan-2-ol, 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroiso-quinolin-1-yl)quinoline;
L) Antifungal biopesticides selected from: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus pumilus (II-50), Bacillus subtilis (II-51), Bacillus subtilis var. amyloliquefaciens (II-52), Candida oleophila I-82, Candida saitoana, Clonostachys rosea f. catenulata, also named Gliocladium catenulatum, Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Metschnikowia fructicola, Microdochium dimerum, Phlebiopsis gigantea, Pseudozyma flocculosa, Pythium oligandrum DV74, Reynoutria sachlinensis, Talaromyces flavus V117b, Trichoderma asperellum SKT-1, T. atroviride LC52, T. harzianum T-22, T. harzianum TH 35, T. harzianum T-39; T. harzianum and T. viride, T. harzianum ICCO12 and T. viride ICC080; T. polysporum and T. harzianum; T. stromaticum, T. virens GL-21, T. viride, T. viride TV1, Ulocladium oudemansii HRU3;
M) Growth regulators selected from: abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassino-lide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride) (II-54), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium, II-55), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid, trinex-apac-ethyl and uniconazole;
N) Herbicides selected from:
acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, me-tolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
amino acid derivatives: bilanafos, glyphosate, glufosinate, sulfosate;
aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
Bipyridyls: diquat, paraquat;
(thio)carbamates: asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;
dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin;
diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen; —hydroxybenzonitriles: bomoxynil, dichlobenil, ioxynil;
imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
phenoxy acetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, pyridate;
pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
sulfonyl ureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuronethyl, chlorsulfuron, cinosul-furon, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nico-sulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosul-furon, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1-((2-chloro-6-propyl-imidazo[1,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimethoxy-pyrimidin-2-yl)urea;
triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;
other acetolactate synthase inhibitors: bispyribac-sodium, cloransulammethyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribam-benz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, py-roxsulam;
other herbicides: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, bicyclopyrone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfa-mide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenoxy]-pyri-din-2-yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2-cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol, 4-amino-3-chloro-6-(4-chloro-phenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid methyl ester, and 4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)-pyridine-2-carboxylic acid methyl ester;
O) Insecticides selected from:
organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phos-phamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenox-ycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zetacypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fen-valerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
insect growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, dif-lubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran, flupyradifurone, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1-2-chloro-thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1,3,5]triazinane;
nicotinic acetylcholine receptor disruptors or allosteric modulators (IRAC Goup 5):
spinosyn (including but not limited to spinosyns A, D, B, C, E, F, G, H, J, and other spinosyn isolates from Saccharopolyspora spinosa culture), spinosad (comprising primarily spinsyns A and D), and derivatives or substituents thereof (including but not limited to tetracyclic and pentacyclic spinosyn derivatives, aziridine spinosyn derivatives, C-5,6 and/or C-13,14 substituted spinosyn derivatives); spinetoram (including but not limited to XDE-175-J, XDE-175-L or other O-ethyl substituted spinosyn derivatives); butenyl-spinosyn and derivatives or substituents thereof (such as isolates from Saccharopolyspora pogona culture);
bioinsecticides including but not limited to Bacillus thuriengiensis, Burkholderia spp, Beauveria bassiana, Metarhizium anisoptiae, Paecilomyces fumosoroseus, and baculoviruses (including but not limited to granuloviruses and nucleopolyhedroviruses);
GABA antagonist compounds: endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1-(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl-1H-pyrazole-3-carbothioic acid amide;
mitochondrial electron transport inhibitor (METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;
Uncouplers: chlorfenapyr;
oxidative phosphorylation inhibitors: cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
moulting disruptor compounds: cryomazine;
mixed function oxidase inhibitors: piperonyl butoxide;
sodium channel blockers: indoxacarb, metaflumizone;
ryanodine receptor inhibitors: chlorantraniliprole, cyantraniliprole, fluben-diamide, N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyra-zole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-car-boxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanyli-dene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide; N-[4,6-di-bromo-2-[(di-2-propyl-lambda-4-sulfanyl-idene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluor-omethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, cy-enopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, pyrifluquinazon, 1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]-methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl] cyclopropaneacetic acid ester; fluensulfone, fluoroalkenyl thioethers; and
P) ribonucleic acid (RNA) and associated compounds including double-stranded RNA (dsRNA), microRNA (miRNA) and small interfering RNA (siRNA); bacteriophages.
13. The synergistic pesticidal composition according to claim 1, wherein a ratio of the concentrations of said pesticidal active ingredient and said C4-C10 saturated or unsaturated aliphatic acid or an agriculturally compatible salt thereof is between about at least one of: 1:15,000 and 15,000:1; 1:10,000 and 10,000:1, 1:5000 and 5000:1, 1:2500 and 2500:1, 1:1500 and 1500:1, 1:1000 and 1000, 1:750 and 750:1, 1:500 and 500:1, 1:400 and 400:1, 1:300 and 300:1, 1:250 and 250:1, 1:200 and 200:1, 1:150 and 150:1, 1:100 and 100:1, 1:90 and 90:1, 1:80 and 80:1, 1:70 and 70:1, 1:60 and 60:1, 1:50 and 50:1, 1:40 and 40:1, 1:30 and 30:1, 1:25 and 25:1, 1:20 and 20:1, 1:15 and 15:1, 1:10 and 10:1, 1:9 and 9:1. 1:8 and 8:1, 1:7 and 7:1, 1:6 and 6:1, 1:5 and 5:1, 1: and 4:1, 1:3 and 3:1, 1:2 and 2:1, 1:1.5 and 1.5:1, and 1.25 and 1.25:1.
14. A method of synergistically enhancing the pesticidal activity of at least one pesticidal active ingredient adapted to control at least one target pest organism comprising:
providing at least one pesticidal active ingredient active for said at least one target pest organism, wherein said pesticidal active ingredient is selected from the list comprising: benzovindiflupyr, bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, oxathiapiprolin, penflufen, penthiopyrad, picoxystrobin, prothioconazole, pydiflumetofen, revysol, sedaxane, trifloxystrobin, pyraclostrobin, azoxystrobin, chlorothalonil, cyprodinil, metalaxyl, epoxiconazole, propiconazole, difenoconazole, fludioxonil, mancozeb, tebuconazole, valifenalate, and combinations thereof;
adding a synergistically effective concentration of at least one C4-C10 saturated or unsaturated aliphatic acid, or an agriculturally acceptable salt thereof, to said pesticidal active ingredient to provide a synergistic pesticidal composition; and
applying said synergistic pesticidal composition in a pesticidally effective concentration to control said at least one target pest organism.
15.-17. (canceled)
18. The method according to claim 14, wherein a ratio of said synergistically effective concentration of said C4-C10 saturated or unsaturated aliphatic acid or an agriculturally compatible salt thereof and said pesticidal active ingredient is between about at least one of: 1:15,000 and 15,000:1; 1:10,000 and 10,000:1, 1:5000 and 5000:1, 1:2500 and 2500:1, 1:1500 and 1500:1, 1:1000 and 1000, 1:750 and 750:1, 1:500 and 500:1, 1:400 and 400:1, 1:300 and 300:1, 1:250 and 250:1, 1:200 and 200:1, 1:150 and 150:1, 1:100 and 100:1, 1:90 and 90:1, 1:80 and 80:1, 1:70 and 70:1, 1:60 and 60:1, 1:50 and 50:1, 1:40 and 40:1, 1:30 and 30:1, 1:25 and 25:1, 1:20 and 20:1, 1:15 and 15:1, 1:10 and 10:1, 1:9 and 9:1. 1:8 and 8:1, 1:7 and 7:1, 1:6 and 6:1, 1:5 and 5:1, 1: and 4:1, 1:3 and 3:1, 1:2 and 2:1, 1:1.5 and 1.5:1, and 1.25 and 1.25:1.
19. The method according to claim 14, wherein the synergistic pesticidal composition has an FIC Index value of less than 1; or preferably less than 0.75, or more preferably less than 0.5.
20. The method according to claim 14, wherein the synergistic pesticidal composition has a predicted probability of synergy of greater than 0.55.
21. A pesticidal composition comprising:
one or more pesticidal agents selected from the list comprising: benzovindiflupyr, bixafen, boscalid, cyproconazole, fenpicoxamid, fenpyrazimine, florylpicoxamid, flutriafol, fluxapyroxad, isopyrazam, isotianil, kresoxim-methyl, metrafenone, oxathiapiprolin, penflufen, penthiopyrad, picoxystrobin, prothioconazole, pydiflumetofen, revysol, sedaxane, trifloxystrobin, pyraclostrobin, azoxystrobin, chlorothalonil, cyprodinil, metalaxyl, epoxiconazole, propiconazole, difenoconazole, fludioxonil, mancozeb, tebuconazole, valifenalate, and combinations thereof; and
one or more saturated or unsaturated C4-C10 aliphatic acids or agriculturally compatible salts thereof,
wherein said one or more saturated or unsaturated C4-C10 aliphatic acids produce a synergistic effect on the pesticidal activity of the pesticidal composition in comparison to the pesticidal activity of the pesticidal agent alone and are present in a respective synergistically active concentration ratio between about 1:15000 and 15000:1.
22. (canceled)
23. The pesticidal composition according to claim 21, wherein the C4-C10 saturated or unsaturated aliphatic acid comprises a C4-C10 unsaturated aliphatic acid, and wherein the unsaturated C4-C10 aliphatic acid comprises at least one of: a trans-2, trans-3, trans-4, trans-5, trans-6, trans-7, trans-8, and trans-9, cis-2, cis-3, cis-4, cis-5, cis-6, cis-7, cis-8, and cis-9 unsaturated bond.
24. (canceled)
25. The synergistic pesticidal composition according to claim 21, wherein the synergistic pesticidal composition has an FIC Index value of less than 1; or preferably less than 0.75, or more preferably less than 0.5.
26. The synergistic pesticidal composition according to claim 21, wherein the synergistic pesticidal composition has a predicted probability of synergy of greater than 0.55.
27. The pesticidal composition according to claim 21, wherein said pesticidal agent comprises at least one pesticidal active ingredient selected from the list comprising:
A) Respiration inhibitors selected from:
inhibitors of complex III at Qo site: azoxystrobin (II-1), coumethoxy-strobin, coumoxystrobin, dimoxystrobin (II-2), enestroburin, fenamin-strobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin (II-3), kresoxim-methyl (II-4), metominostrobin, orysastrobin (II-5), picoxystrobin (II-6), pyraclostrobin (II-7), pyrametostrobin, pyraoxystrobin, trifloxystrobin (II-8), 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneamino-oxymethyl)-phe-nyl)-2-methoxyimino-N-methyl-acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, fenamidone;
Inhibitors of complex III at Qi site: cyazofamid, amisulbrom, [(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)-amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbony-loxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol5-ylmethoxy)-4-methoxy-pyridine-2-carbon-yl]amino]-6-methyl-4,9-dioxol,5-dioxonan-7-yl] 2-methylpropanoate; (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenyl-methyl)-1,5-dioxonan-7-yl 2-methylpropanoate;
Inhibitors of complex II: benodanil, benzovindiflupyr (II-9), bixafen (II-10), boscalid (II-11), carboxin, fenfuram, fluopyram (II-12), flutolanil, fluxapyroxad (II-13), furametpyr, isofetamid, isopyrazam (II-14), mepronil, oxycarboxin, penflufen (II-15), penthiopyrad (II-16), sedaxane (II-17), tecloftalam, thifluzamide, N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide, 3-(difluorome-thyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, N-(7-fluoro-1,1,3-trime-thyl-indan-4-yl)-1,3-dimethyl-pyrazole-4-carboxamide, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide;
Other respiration inhibitors: diflumetorim, (5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluorometh-ylpyridin-2-yloxy)-phenyl]-ethyl}-amine; binapacryl, dinobuton, dinocap, fluazinam (II-18); ferimzone; fentin salts such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin (II-19); and silthiofam;
B) Sterol biosynthesis inhibitors (SBI fungicides) selected from:
C14 demethylase inhibitors (DMI fungicides): azaconazole, bitertanol, bromuconazole, cyproconazole (II-20), difenoconazole (II-21), diniconazole, diniconazole-M, epoxiconazole (II-22), fenbuconazole, fluquinconazole (II-23), flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole (II-24), myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole (II-25), prothioconazole (II-26), simeconazole, tebuconazole (II-27), tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole; imazalil, pefurazoate, prochloraz, triflumizol; fenarimol, nuarimol, pyrifenox, triforine, [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol;
Delta14-reductase inhibitors: aldimorph, dodemorph, dodemorphacetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
Inhibitors of 3-keto reductase: fenhexamid;
C) Nucleic acid synthesis inhibitors selected from:
phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam) (II-38), ofurace, oxadixyl;
others nucleic acid inhibitors: hymexazole, octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;
D) Inhibitors of cell division and cytoskeleton selected from:
tubulin inhibitors: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl (II-39); 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine
other cell division inhibitors: diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone (II-40), pyriofenone;
E) Inhibitors of amino acid and protein synthesis selected from:
methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil, mepanipyrim, Pyrimethanil (II-41);
protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
F) Signal transduction inhibitors selected from:
MAP/histidine kinase inhibitors: fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
G protein inhibitors: quinoxyfen;
G) Lipid and membrane synthesis inhibitors selected from:
Phospholipid biosynthesis inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; propamocarb, propamocarb-hydrochloride;
lipid peroxidation inhibitors: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
phospholipid biosynthesis and cell wall deposition: dimethomorph (II-42), flumorph, mandipropamid (II-43), pyrimorph, benthiavalicarb, iprovalicarb, valifenalate, N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
acid amide hydrolase inhibitors: oxathiapiprolin;
H) Inhibitors with Multi Site Action selected from:
inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride (II-44), basic copper sulfate, sulfur;
thio- and dithiocarbamates: ferbam, mancozeb (II-45), maneb, metam, metiram (II-46), propineb, thiram, zineb, ziram;
organochlorine compounds: anilazine, Chlorothalonil (II-47), captafol, captan, folpet, dichlofluanid, dichlorophen, hexachlorobenzene, pentachlorophenole and its salts, phthalide, tolylfluanid, N-(4-chlo-ro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
guanidines and others: guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoc-tadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon, 2,6-dimethyl-1H,5H-[1,4]dithii-no[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone (II-48);
I) Cell wall synthesis inhibitors selected from:
inhibitors of glucan synthesis: validamycin, polyoxin B;
melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamid, dicyclomet, fenoxanil;
J) Plant defence inducers selected from:
acibenzolar-S-methyl, probenazole, isotianil, tiadinil, prohexadione-calcium; fosetyl, fosetyl-aluminum, phosphorous acid and its salts (II-49);
K) Unknown mode of action selected from: bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover, flusulfamide, flutianil, methasulfocarb, nitrapyrin, nitrothal-isopropyl, oxathiapiprolin, tolprocarb, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl1-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, 2-[3,5-bis-(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yl-oxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]-ethanone, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-15-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen-4-one, N-(cyclo-propylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methyl formamidine, N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, methoxyacetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester, 3-[5-(4-meth-ylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole), N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide, 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole, 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phe-nyl)-isoxazol-5-yl]-2-prop2-ynyloxy-acetamide, ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate, tertbutyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]-amino]oxymethyl]-2-pyridyl]carbamate, pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, 2-[2-[(7,8-dif-luoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-qui-nolyl)oxy]phenyl]propan-2-ol, 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroiso-quinolin-1-yl)quinoline;
Fenpicoxamid, florylpicoxamid;
L) Antifungal biopesticides selected from: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus pumilus (II-50), Bacillus subtilis (II-51), Bacillus subtilis var. amyloliquefaciens (II-52), Candida oleophila I-82, Candida saitoana, Clonostachys rosea f. catenulata, also named Gliocladium catenulatum, Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Metschnikowia fructicola, Microdochium dimerum, Phlebiopsis gigantea, Pseudozyma flocculosa, Pythium oligandrum DV74, Reynoutria sachlinensis, Talaromyces flavus V117b, Trichoderma asperellum SKT-1, T. atroviride LC52, T. harzianum T-22, T. harzianum TH 35, T. harzianum T-39; T. harzianum and T. viride, T. harzianum ICCO12 and T. viride ICC080; T. polysporum and T. harzianum; T. stromaticum, T. virens GL-21, T. viride, T. viride TV1, Ulocladium oudemansii HRU3;
M) Growth regulators selected from: abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassino-lide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride) (II-54), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium, II-55), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid, trinex-apac-ethyl and uniconazole;
N) Herbicides selected from:
acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, me-tolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
amino acid derivatives: bilanafos, glyphosate, glufosinate, sulfosate;
aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
Bipyridyls: diquat, paraquat;
(thio)carbamates: asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;
dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin;
diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen; —hydroxybenzonitriles: bomoxynil, dichlobenil, ioxynil;
imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
phenoxy acetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, pyridate;
pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
sulfonyl ureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuronethyl, chlorsulfuron, cinosul-furon, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nico-sulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosul-furon, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1-((2-chloro-6-propyl-imidazo[1,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimethoxy-pyrimidin-2-yl)urea;
triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;
other acetolactate synthase inhibitors: bispyribac-sodium, cloransulammethyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribam-benz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, py-roxsulam;
other herbicides: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, bicyclopyrone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfa-mide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenoxy]-pyri-din-2-yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2-cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol, 4-amino-3-chloro-6-(4-chloro-phenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid methyl ester, and 4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)-pyridine-2-carboxylic acid methyl ester;
O) Insecticides selected from:
organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phos-phamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenox-ycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zetacypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fen-valerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
insect growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, dif-lubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran, flupyradifurone, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1-2-chloro-thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1,3,5]triazinane;
nicotinic acetylcholine receptor disruptors or allosteric modulators (IRAC Goup 5): spinosyn (including but not limited to spinosyns A, D, B, C, E, F, G, H, J, and other spinosyn isolates from Saccharopolyspora spinosa culture), spinosad (comprising primarily spinsyns A and D), and derivatives or substituents thereof (including but not limited to tetracyclic and pentacyclic spinosyn derivatives, aziridine spinosyn derivatives, C-5,6 and/or C-13,14 substituted spinosyn derivatives); spinetoram (including but not limited to XDE-175-J, XDE-175-L or other O-ethyl substituted spinosyn derivatives); butenyl-spinosyn and derivatives or substituents thereof (such as isolates from Saccharopolyspora pogona culture);
bioinsecticides including but not limited to Bacillus thuriengiensis, Burkholderia spp, Beauveria bassiana, Metarhizium anisoptiae, Paecilomyces fumosoroseus, and baculoviruses (including but not limited to granuloviruses and nucleopolyhedroviruses);
GABA antagonist compounds: endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1-(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl-1H-pyrazole-3-carbothioic acid amide;
mitochondrial electron transport inhibitor (METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;
Uncouplers: chlorfenapyr;
oxidative phosphorylation inhibitors: cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
moulting disruptor compounds: cryomazine;
mixed function oxidase inhibitors: piperonyl butoxide;
sodium channel blockers: indoxacarb, metaflumizone;
ryanodine receptor inhibitors: chlorantraniliprole, cyantraniliprole, fluben-diamide, N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyra-zole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-car-boxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanyli-dene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide; N-[4,6-di-bromo-2-[(di-2-propyl-lambda-4-sulfanyl-idene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluor-omethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, pyrifluquinazon, 1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]-methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl] cyclopropaneacetic acid ester; fluensulfone, fluoroalkenyl thioethers; and
P) ribonucleic acid (RNA) and associated compounds including double-stranded RNA (dsRNA), microRNA (miRNA) and small interfering RNA (siRNA); bacteriophages.
28. The pesticidal composition according to claim 21, wherein said pesticidal agent comprises at least one of: a fungicide, nematicide, insecticide, acaricide, herbicide, molluscicide, and a bactericide.
29.-33. (canceled)
34. The synergistic pesticidal composition according to claim 1, wherein said C4-C10 saturated or unsaturated aliphatic acid comprises at least one substituent selected from the list comprising: hydroxy-alkyl- and amino-substituents.
35. The synergistic pesticidal composition according to claim 1, wherein the pesticidal active ingredient is selected from at least one of: a fungicide having a fungicidal mode of action inhibiting a cellular membrane cytochrome bc1 complex, and a fungicide having a fungicidal mode of action inhibiting a cellular membrane cytochrome p450 complex.
36. The synergistic pesticidal composition according to claim 1, wherein the pesticidal active ingredient comprises at least one of a strobilurin fungicide, and a triazole fungicide.
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