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GB2533083B - An agrochemical composition, a method of preparing the same and the use thereof - Google Patents

An agrochemical composition, a method of preparing the same and the use thereof Download PDF

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Publication number
GB2533083B
GB2533083B GB1421408.4A GB201421408A GB2533083B GB 2533083 B GB2533083 B GB 2533083B GB 201421408 A GB201421408 A GB 201421408A GB 2533083 B GB2533083 B GB 2533083B
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GB
United Kingdom
Prior art keywords
composition according
dipropylene
glycol dibenzoate
diethylene glycol
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
GB1421408.4A
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GB201421408D0 (en
GB2533083A (en
Inventor
Timothy Bristow James
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Rotam Agrochem International Co Ltd
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Rotam Agrochem International Co Ltd
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Priority to GB1421408.4A priority Critical patent/GB2533083B/en
Application filed by Rotam Agrochem International Co Ltd filed Critical Rotam Agrochem International Co Ltd
Priority to GB1906116.7A priority patent/GB2571647B/en
Publication of GB201421408D0 publication Critical patent/GB201421408D0/en
Priority to PCT/CN2015/092256 priority patent/WO2016086726A1/en
Priority to ARP150103612A priority patent/AR102564A1/en
Priority to TW104139828A priority patent/TWI688338B/en
Priority to CN201510872655.2A priority patent/CN105638656B/en
Priority to BR102015030210-0A priority patent/BR102015030210B1/en
Publication of GB2533083A publication Critical patent/GB2533083A/en
Application granted granted Critical
Publication of GB2533083B publication Critical patent/GB2533083B/en
Expired - Fee Related legal-status Critical Current
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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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • 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
    • A01N35/08—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 at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—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 at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • 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
    • 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
    • A01N43/72—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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or 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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

AN AGROCHEMCIAL COMPOSITION, A METHOD OF PREPARING THE SAMEAND THE USE THEREOF
The present invention relates to an agrochemical composition. The presentinvention further relates to a method of preparing the aforementioned composition andits use in crop protection. The present invention is also related to the reduction ofeye irritation caused by the agrochemical composition, in particular a liquidconcentrate formulation of the composition.
Emulsifiable concentrate (EC) formulations are a very popular formulation typefor the preparation and use of compositions comprising agrochemically activecomponents. However, such formulations require substantial quantities of organicsolvents, such as aromatic hydrocarbons, chlorinated hydrocarbons, and the like,together with anionic and non-ionic emulsifiers to stabilize the active ingredients in theformulations. With this combination of components, the formulated products are of agood quality and generally perform well in field applications. However, most of theproducts formulated in this manner cause severe eye irritation to users. As a result,such formulations are often classed as being hazardous. For example, emulsifiableconcentrates are classified as Toxicity Category I (Cat I) in Brazil. Knowing thatformulations labeled with “Toxicity Category I” may cause eye irritation, farmers andother end users are reluctant to purchase and use such products.
The prior art does not offer a solution for the problems of using solvents andemulsifiers in emulsion concentrate (EC) formulations. At present, commercialemulsion concentrate formulations cause severe eye irritation. As a result, attemptshave been made to avoid the use organic solvents such as aromatic or chlorinatedhydrocarbons, and instead use alternative solvents having reduced toxic effects.Examples of such alternative solvents are aliphatic hydrocarbons, alcohols, glycols,polyglycols, glycol ethers, ketones, as well as polar solvents with a high solvent power,such as gamma-butyrolactone, N-methyl pyrrolidone, and the like.
However, eye irritation is caused not only by the solvents, but can also becaused by active ingredients and emulsifiers present in the formulation. Theemulsifiers, for example anionic emulsifiers, are important to increase spontaneousdispersibility of the formulation in water and stability of the diluted formulation.Calcium alkylbenzene sulfonate is one type of anionic emulsifier frequently used inemulsion concentrate formulations. However, these kind of anionic emulsifierscause severe eye irritation. Consequently, even if the composition is formulated withsolvents that are non-irritant to the eyes, the formulation may still cause severe eyeirritation because of the presence of active ingredients and emulsifiers. WO 02/045507 describes a microemulsifiable concentrate comprising ahydrophobic active ingredient and at least one surfactant dissolved in a solventsystem comprising a hydrophobic water-insoluble alkyl alkanolate, as a first solvent,and a polyhydric alcohol or a condensate of polyhydric alcohols and mixtures thereof,as a second solvent. The formulations are reported to exhibit reduced eye irritation. WO 2006/002984 discloses a liquid concentrate composition comprising awater-insoluble active ingredient, at least one organic solvent having a water solubilityof at least 10 g/L, and at least one non-ionic block copolymer comprising at least onepolyethylene oxide moiety and at least one hydrophobic polyether moiety. Theorganic solvent is capable of dissolving the active ingredient. The problem of eyeirritation is not discussed or otherwise addressed in WO 2006/002984.
There is an ongoing need to find safe, preferably substantially inert,components for formulating liquid concentrates, with a view to providing a formulationwhich will not irritate the eyes. It would be advantageous if the formulationcomponents could also reduce the irritancy of the active ingredients and emulsifiers tothe eyes of users.
It has now been surprisingly found that certain dipropylene/diethylene glycoldibenzoates are not only non-irritant to the eyes, but also reduce the eye irritationcaused by the active ingredients and emulsifiers present in the formulation.
Accordingly, in a first aspect, the present invention provides an emulsifiableconcentrate (EC) agrochemical composition comprising at least onedipropylene/diethylene glycol dibenzoate, at least one active ingredient and at leastone emulsifier, wherein the active ingredient comprises a compound selected frompyripoxyfen, clomazone, a pyrethroid ester, a cyclohexime oxime, abenzoylphenylurea chitin synthesis inhibitor, and an avermectin.
Dipropylene/diethylene glycol dibenzoates are themselves not irritants. It hasbeen found that the presence of the dipropylene/diethylene glycol dibenzoate in theagrochemical composition significantly reduces the toxicity of the formulation, inparticular reducing the irritancy of the formulation to the eyes. In particular, itappears that the dipropylene/diethylene glycol dibenzoate reduces or substantiallynegates the irritancy of the active ingredients and emulsifiers to the eyes.
As described in more detail below, it has been found thatdipropylene/diethylene glycol dibenzoate is effective in reducing the irritancy of liquidconcentrate formuilations. Thus, the inclusion of dipropylene/diethylene glycoldibenzoate in liquid concentrates reduces the eye irritancy of the formulation. Inaddition, it has been found that the use of dipropylene/diethylene glycol dibenzoate inliquid concentrate pesticidal formulations is environmentally friendly.
The dipropylene/diethylene glycol dibenzoate is present in the composition ofthe present invention in an amount sufficient to reduce the irritancy of the othercomponents in the composition, in particular the eye irritation of the active ingredientsand emulsifiers present. The amount of dipropylene/diethylene glycol dibenzoaterequired will be determined by the particular active ingredients and emulsifiersemployed in the composition and their amounts. The amount of thedipropylene/diethylene glycol dibenzoate required to reduce or eliminate the irritancy to the eyes of the formulation may be determined without undue experimentation bythe skilled person, for example by trial and error.
The dipropylene/diethylene glycol dibenzoate is effective to reduce the eyeirritancy of the active ingredient when present in a wide range of weight ratios to theactive ingredient. The dipropylene/diethylene glycol dibenzoate is preferably presentin an amount at least equal to or, more preferably in excess of the amount of theactive ingredient. The weight ratio of the dipropylene/diethylene glycol dibenzoate tothe active ingredient is preferably at least 1:1, in some preferred embodiments at least1:2, in other preferred embodiments at least 1:3. In particular, thedipropylene/diethylene glycol dibenzoate is preferably present in an amount toprovide a weight ratio of the active ingredient to the dipropylene/diethylene glycoldibenzoate from 1:1 to 1:100, preferably from 1:1 to 1:90, more preferably from 1:2 to1:20, still more preferably from 1:3 to 1:15.
The dipropylene/diethylene glycol dibenzoate is effective in reducing the eyeirritancy of emulsifiers in a wide range of weight ratios. In many embodiments, thedipropylene/diethylene glycol dibenzoate is present in the composition in an amountat least equal to, more preferably in excess, of the total amount of the emulsifierpresent. The weight ratio of the dipropylene/diethylene glycol dibenzoate to the totalemulsifier content of the composition is preferably at least 0.1, more preferably atleast 0.2. The weight ratio of the dipropylene/diethylene glycol dibenzoate to thetotal emulsifier content of the composition may be from 0.1 to 60, preferably from 0.2to 60. In a number of embodiments, a weight ratio of from 0.3 to 10, moreparticularly from 0.4 to 8 has been found to be effective. Higher amounts of thedipropylene/diethylene glycol dibenzoate may be employed, for example in weightratios to the emulsifier content of from 10 to 50. In many embodiments, a weightratio of dipropylene/diethylene glycol dibenzoate to the emulsifier content of less than15, more preferably less than 10 is effective.
The dipropylene/diethylene glycol dibenzoate may be present in thecomposition in an amount of at least 2% by weight, preferably from 10% by weight,more preferably from 20% by weight. In preferred embodiments, thedipropylene/diethylene glycol dibenzoate is present in the composition in an amount of from 2 to 90% by weight, preferably from 10 to 80% be weight, more preferablyfrom 20 to 70% by weight of the composition.
The composition may comprise dipropylene glycol dibenzoate, diethyleneglycol dibenzoate or a combination of dipropylene glycol dibenzoate and diethyleneglycol dibenzoate.
As mentioned above, the present invention provides an agrochemicalcomposition comprising at least one agrochemically active ingredient. It has beenfound that the presence of one or more dipropylene/diethylene glycol dibenzoates iseffective in reducing the irritancy of a range of active ingredients. Suitable activeingredients for use in the composition of the present invention are well known in theart and are commercially available.
As noted above, the dipropylene/diethylene glycol dibenzoates have beenfound to be effective in reducing the toxicity, in particular the irritancy to eyes, of arange of active ingredients. In one embodiment, the composition of the presentinvention comprises, as an active ingredient clomazone (2-(2-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one).
It has also been found that the dipropylene/diethylene glycol dibenzoates areeffective in reducing the toxicity, in particular the irritancy to eyes, of pyrethroid esteracaricides and insecticides. Such pyrethroids are known in the art and include, forexample, cyhalothrin ((/TS)-a-cyano-3-phenoxybenzyl (2)-(1 RS,3RS)-3-(2-ch\oro-3,3,3-trifluoroprop-1 -enyl)-2,2-dimethylcyclopropanecarboxylate), cypermethrin ((RS)-a-cyano-3-phenoxybenzyl (1 i?S,3i?S;1 i?S,3Si?)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate), deltamethrin ((S)-a-cyano-3-phenoxybenzyl ()R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate), lambda-cyhalothrin ((S)-a-cyano-3-phenoxybenzyl (2)-(1 R,3F?)-3-(2-chloro-3,3,3-trifluoroprop-1 -enyl)-2,2-dimethylcyclopropanecarboxylate and (/7)-cyano-3-phenoxybenzyl(2)-(1 S, 3S)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate). A particularly suitable pyrethroid is bifenthrin.
In one embodiment, the composition of the present invention comprises, as anactive ingredient pyriproxyfen (4-phenoxyphenyl (HS)-2-(2-pyridyloxy)propyl ether).
It has also been found that the dipropylene/diethylene glycol dibenzoates areeffective in reducing the toxicity, in particular the irritancy to eyes, of cycloheximeoxime herbicides, including alloxydim (methyl (1/TS)-3-[(E)-1-(allyloxyimino)butyl]-4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-enecarboxylate),butroxydim ((5/z?S)-5-(3-butyryl-2,4,6-trimethylphenyl)-2-[(EZ)-1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-one), clethodim ((5HS)-2-{(1 EZ)-1-[(2E)-3-chloroallyloxyimino]propyl}-5-[(2/:?S)-2-(ethylthio)propyl]-3-hydroxycyclohex-2-en-1-one),cloproxydim ((5/z?S)-2-{(EZ)-1-[(2EZ)-3-chloroallyloxyimino]butyl}-5-[(2/z?S)-2-(ethylthio)propyl]-3-hydroxycyclohex-2-en-1 -one), cycloxydim ((5HS)-2-[(E2)-1 -(ethoxyimino)butyl]-3-hydroxy-5-[(3/:?S)-thian-3-yl]cyclohex-2-en-1 -one), profoxydim ((5HS)-2-{(EZ)-1-[(2HS)-2-(4-chlorophenoxy)propoxyimino]butyl}-3-hydroxy-5-[(3/:?S)-thian-3-yl]cyclohex-2-en-1 -one), sethoxydim ((5HS)-2-[(EZ)-1 -(ethoxyimino)butyl]-5-[(2/:?S)-2-(ethylthio)propyl]-3-hydroxycyclohex-2-en-1 -one), tepraloxydim ((5HS)-2-{(EZ)-1 -[(2E)-3-chloroallyloxyimino]propyl}-3-hydroxy-5-perhydropyran-4-ylcyclohex-2-en-1-one), and tralkoxydim ((HS)-2-[(EZ)-1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-en-1 -one). The dipropylene/diethylene glycoldibenzoates are particularly effective in reducing the irritancy of clethodim.
It has further been found that the dipropylene/diethylene glycol dibenzoatesare effective in reducing the toxicity, in particular the irritancy to eyes, ofbenzoylphenylurea chitin synthesis inhibitors , including bistrifluron(1-[2-chloro-3,5-bis(trifluoromethyl)phenyl]-3-(2,6-difluorobenzoyl)urea),chlorbenzuron (1-(2-chlorobenzoyl)-3-(4-chlorophenyl)urea), chlorfluazuron (1 -[3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluorobenzoyl)urea), dichlorbenzuron (1 -(4-chlorophenyl)-3-(2,6-dichlorobenzoyl)urea),diflubenzuron (1 -(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea), flucycloxuron(1-{a-[(EZ)-4-chloro-a-cyclopropylbenzylideneaminooxy]-p-tolyl}-3-(2,6-difluoro benzoyl)urea (ratio 50-80% (E)- and 50-20% (Z)-isomers),flufenoxuron (1-[4-(2-chloro-a,a,a-trifluoro-p-tolyloxy)-2-fluorophenyl]-3-(2,6-difluorobenzoyl)urea), hexaflumuron (1-[3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea), lufenuron ((RS)-1-[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-3-(2,6-difluorobenzoyl)urea), novaluron ((RS)-1 -[3-chloro-4-(1,1,2-trifluoro-2-trifluoromethoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea),noviflumuron (1-{3,5-dichloro-2-fluoro-4-[(RS)-1,1,2,3,3,3-hexafluoropropoxy]phenyl}-3-(2,6-difluorobenzoyl)urea), penfluron (1 -(2,6-difluorobenzoyl)-3-(a,a,a-trifluoro-p-tolyl)urea), teflubenzuron (1 -(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea), and triflumuron (1-(2-chlorobenzoyl)-3-(4-trifluoromethoxyphenyl)urea). Thedipropylene/diethylene glycol dibenzoates are particularly effective in reducing theirritancy of lufenuron.
It has further been found that the dipropylene/diethylene glycol dibenzoatesare effective in reducing the toxicity, in particular the irritancy to eyes, of avermectininsecticides, acaracides and nematacides, including abamectin (mixture of > 80%(10E,14E,16E)-(1R,4S,5'S,6S,6'R,8R,12S,13S,20R,21R,24S)-6'-[(S)-sec-butyl]-21,24-dihydroxy-5', 11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14'8.O20,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-2'/-/-pyran)-12-yl2,6-dideoxy-4-0-(2,6-dideoxy-3-0-methyl-a-L-arab/no-hexopyranosyl)-3-O-methyl-a-L-arab/no-hexopyranoside and < 20% (10E,14E,16E)-(1fi,4S,5'S,6S,6'fi,8fi,12S,13S,20fi,21fi,24S)-21,24-dihydroxy-6'-isopropyl-5',11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-2'/-/-pyran)- 12-yl 2,6-dideoxy-4-0-(2,6-dideoxy-3-0-methyl-a-L-arab/no-hexopyranosyl)-3-0-methyl-a-L-arab/no-hexopyranoside),doramectin ((10E,14E,16E)-(1H,4S,5'S,6S,6'H,8H,12S,13S,20H,21H,24S)-6'-cyclohexyl-21,24-dihydroxy-5',11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.02°’24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-2'A/-pyran)-12-yl 2,6-dideoxy-4-0-(2,6-dideoxy-3-0-methyl-a-L-arab/no-hexopyranosyl)-3-C>-methyl-a-L-arab/no-hexopyranoside), emamectin (mixture of > 90%(10E,14E,16E)-(1fi,4S,5'S,6S,6'fi,8fi,12S,13S,20fi,21fi,24S)-6'-[(S)-sec-butyl]-21,24-dihydroxy-5', 11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-2'/-/-pyran)-12-yl 2,6-dideoxy-3-0-methyl-4-0-(2,4,6-trideoxy-3-0-methyl-4-methylamino-a-L-/yxo-hexapyranosyl)-a -L-arab/no-hexapyranoside and < 10% (10E,14E,16E)- (1 R,4S,5'S,6S,6'R,8R, 12S, 13S,205,21 R,243)-21,24-dihydroxy-6'-isopropyl-5', 11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-2'5-pyran)-12-yl 2,6-dideoxy-3-0-methyl-4-0-(2,4,6-trideoxy-3-0-methyl-4-methylamino-a-L-/yxO-hexapyranosyl)-a-L-arab/no-hexapyranoside), eprinomection (mixture of (10E,14E,16E)-(1 R,4S,5'S,QS,Q'R,8R, 12S, 13S,205,215,24S)-6'-[(S)-sec-butyl]-21,24-dihydroxy-5', 11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-2'5-pyran)-12-yl 4-0-(4-acetamido-2,4,6-trideoxy-3-0-methyl-a-L-/yxo-hexopyranosyl)-2,6-dideoxy-3-0-methyl-a-L-arab/no-hexopyranoside (majorcomponent) and (10E,14E,16E)-(15,4S,5'S,6S,6'5,85,12S,13S,205, 215.245) -21,24-dihydroxy-6'-isopropyl-5',11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-2'5-pyran)-12-yl 4-0-(4-acetamido-2,4,6-trideoxy-3-0-methyl-a-L-/yxo-hexopyranosyl)-2,6-dideoxy-3-0-methyl-a-L-arab/no-hexopyranoside (minorcomponent)), ivermectin (mixture of (10E,14E,16E)-(15,4S,5'S,65,6'5,85,12S, 135.205.215.245) -6'-[(S)-sec-butyl]-21,24-dihydroxy-5',11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(tetrahydropyran)- 12-yl 2,6-dideoxy-4-0-(2,6-dideoxy-3-0-methyl-a-L-arab/no-hexopyranosyl)-3-0-methyl-a-L-arab/no-hexopyranoside and (10E, 14E, 165)-(15,4S,5'S,65,6'5,85,12S,13S,205,215,24S)-21,24-dihydroxy-6'-isopropyl-5',11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2’-(tetrahydropyran)-12-yl 2,6-dideoxy-4-0-(2,6-dideoxy-3-0-methyl-a-L-arab/no-hexopyranosyl)-3-0-methyl-a-L-arab/no-hexopyranoside), and selamectin((10E,14E,16E,21Z)-(15,4S,5'S,65,6'S,85,12S,13S,205,215,24S)-6'-cyclohexyl-24-hydroxy-21-hydroxyimino-5',11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6. 1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(tetrahydropyran)-12-yl2,6-dideoxy-3-0-methyl-a-L-arab/no-hexopyranoside). The dipropylene/diethyleneglycol dibenzoates are particularly effective in reducing the irritancy of abamectin.
It has been found that the composition of the present invention is particularlyeffective when the active ingredient is selected from clomazone, bifenthrin,pyriproxyfen, clethodim, lufenuron, abamectin and mixtures thereof.
The present invention provides an agrochemical composition furthercomprising at least one emulsifier. Suitable emulsifiers for use in the compositionare well known in the art and are commercially available. The emulsifier or emulsifiermixture is selected to have good emulsifying, dispersing and wetting abilities in theformulation employed. The emulsifier may be selected from non-ionic emulsifiers,ionic emulsifiers, cationic emulsifiers and mixtures thereof.
Preferred non-ionic emulsifiers are those selected from alcohol alkoxylates,alkylphenol ethoxylates, alkylpolysaccharides, amine ethoxylates, castor oilethoxylates, sorbitan fatty acid ester ethoxylates, and polyoxyethylene fatty acids.
Preferred anionic emulsifiers are water-soluble soaps as well as water-solublesynthetic emulsifiers. Typical examples of anionic emulsifiers are selected fromamine alkylbenzenesulfonate, ammonium dodecylbenzene sulfonate, calciumalkylsulphonate, and calcium alkylbenzenesulfonate.
Preferred cationic emulsifiers in the composition of the present invention maybe quaternary ammonium salts having the following general formula:
in which R1; R2, R3 or R4each represents at least one C8 to C22 alkyl radical, or RbR2, R3 or R4each represents an unsubstituted or halogenated lower alkyl, benzyl, orhydroxyl- lower alkyl radicals; and X represents a halide, for example a chlorine ion,methyl sulfate or ethyl sulfate. Examples of preferred cationic emulsifiers arepolyoxyethylene quaternary and polyoxyethylene tallow ethylmonium ethosulfate,
stearyltrimethylammonium chloride, benzyl bis(2-chloroethyl)ethylammoniumbromide.
The emulsifier or emulsifier mixture may be present in the composition in anysuitable amount. Preferably, the emulsifier is present in the composition in anamount of at least 5% by weight, more preferably at least 10% by weight, still morepreferably at least 15% by weight. Preferably, the one or more emulsifiers arepresent in an amount in the range of from 5 to 40% by weight, more preferably from 5to 35% by weight, still more preferably from 10 to 30% by weight of the composition.An amount of one or more emulsifiers of from 20 to 30% by weight of the compositionhas been found to be particularly suitable in many embodiments.
In addition to dipropylene/diethylene glycol dibenzoate, at least one activeingredient and at least one emulsifier, the compositions of the present invention mayalso comprise other components as is known in the art, depending upon the type offormulation being employed.
For example, the composition may comprise one or more solvents, in particularone or more polar or non-polar organic solvents. Suitable solvents are known in theart and are commercially available. Suitable polar or non-polar organic solventsinclude alcohols, such as benzyl alcohol, alkyl pyrrolidones, such asN-methylprrolidone, N-octylpyrrolidone, or one or more lactones, such asγ-butyrolactone; aromatic hydrocarbons and mixtures thereof, such as thecommercially available solvent compositions SOLVESSOR™100 andSOLVESSOR™200, and dimethyl sulfoxide.
Further components that may be included in the composition are well known inthe art and include one or more stabilizers, one or more thickeners, and the like.Such components are commercially available and their uses in formulating theagrochemical compositions are recognized and understood by the person skilled inthe art.
The composition of the present invention is a liquid concentrate, in particularan emulsifiable concentrate (EC) formulation. The liquid concentrate formulationsmay comprise active ingredients that are sparingly water-soluble or water-insoluble.The liquid concentrate formulations are preferably those for dispersion in water, priorto use.
In a further aspect, the present disclosure provides a liquid concentratecomposition comprising at least one dipropylene/diethylene glycol dibenzoate, at leastone active ingredient and at least one emulsifier.
The present disclosure also provides, in a further aspect, a method forpreparing an agrochemical composition, the method comprising combining at leastone dipropylene/diethylene glycol dibenzoate with at least one active ingredient and atleast one emulsifier.
The compositions of the present invention may be prepared using techniquesknown in the art. A particularly preferred method for preparing the liquid concentratecomposition is as follows:
Each component is provided according to the weight fraction required in thefinal composition. First, a solvent and dipropylene/diethylene glycol dibenzoate areadded to a suitable mixing vessel, for example a blending tank, and mixed to form amixture. The active ingredient is then added to the mixture and mixed continuously(typically for about 30 minutes) until the active ingredient dissolves completely in thesolvent. Thereafter, the one or more emulsifiers and the further components, ifpresent, are added to the mixture and mixed (typically for about an hour) to ensurehomogeneity.
In a further aspect, the present disclosure provides the use of at least onedipropylene/diethylene glycol dibenzoate to reduce the eye irritancy of an activeingredient and an emulsifier in an agrochemical formulation.
In a further aspect, the present disclosure provides a method for reducing theeye irritation of liquid formulations caused by the active ingredients and emulsifiers,the method comprising adding at least one dipropylene/diethylene glycol dibenzoateto the formulation in an amount sufficient to reduce the eye irritancy of the formulation.
In a still further aspect, the present invention provides a method for treatingpests at a locus comprising applying to the locus a composition as hereinbeforedescribed.
Embodiments of the present invention will now be described, for illustrationpurposes only, by way of the following examples.
EXAMPLES
In each of the following examples, a composition was prepared according tothe following general methodology:
In general, each component was added to a vessel in an amount based uponthe particular composition recipe indicate. More particularly, first, the solvent anddipropylene/diethylene glycol dibenzoate were added to a blending tank in thespecified amounts and mixed to form a mixture. At least one active ingredient wasadded to the mixture and mixed continuously for about 30 minutes until the activeingredient was dissolved completely. Thereafter, the emulsifier was added to theblending tank and the resulting mixture mixed continuously for about an hour until themixture was uniform, after which mixing was stopped. Finally, the mixture wasdischarged from the blending tank.
The eye irritation potential of each formulation was determined according tothe method described by N. P. Luepke: Tien's Egg Chorio Allantoic Membrane Testfor Irritation Potential’, Fd. Chem. Toxic. 23 (1985), pp 287-291, (hereafter theΉΕΤ-CAM Test’), which was modified according to the method of H. Spielmann (H.Spielmann: Methods in Molecular Biology 43 (1995) pp. 199-204, and H. Spielmannet al. ATLA 24 (1996), pp. 741-858).
In the HET-CAM Test, a chorioallantoic membrane (CAM) was treated withsamples of each composition. The chorioallantoic membrane was then observed for5 minutes. The severity of haemorrhage, lysis and coagulation were examined.The samples were categorized as follows:
Category 0 (Cat 0): strongly irritant
Category I (Cat I): irritant
Category II (Cat II): moderate irritant
Category III (Cat III): non-irritant
Samples and controls were prepared for each formulation. The eye irritationpotential of the samples and controls were examined as mentioned above. In eachexample, the control composition is identical to the sample composition, with theexception that dipropylene/diethylene glycol dibenzoate was omitted.
Example 1
Emulsion concentrate compositions Sample 1 and Control 1 were preparedaccording to the recipe specified in Table 1 below. The ratio of bifenthrin anddipropylene glycol dibenzoate of Sample 1 was approximately 1:13. The eyeirritancy of Sample 1 was compared with that of Control 1 (that is the composition ofSample 1 without the addition of dipropylene glycol dibenzoate).
Table 1
Example 2
Emulsion concentrate compositions Sample 2 and Control 2 were preparedaccording to the recipe set out in Table 2 below. The ratio of bifenthrin anddiethylene glycol dibenzoate of Sample 2 was approximately 1:1. The eye irritation
of Sample 2 was compared with that of Control 2 (without the addition of diethyleneglycol dibenzoate).
Table 2
Example 3
Emulsion concentrate compositions Sample 3 and Control 3 were prepared withcomponents according to Table 3 below. The ratio of bifenthrin and dipropyleneglycol dibenzoate of Sample 3 was approximately 1:2. The eye irritation of Sample 3was compared with that Control 3 (without the addition of dipropylene glycoldibenzoate).
Table 3
Example 4
Emulsion concentrate compositions Sample 4 and Control 4 were prepared withcomponents as set out in Table 4 below. The ratio of clethodim and diethylene glycoldibenzoate of Sample 4 was approximately 1:3. The eye irritation of Sample 4 wascompared with that of Control 4 (without the addition of diethylene glycol dibenzoate).Table 4
Example 5
Emulsion concentrate compositions Sample 5 and Control 5 were prepared withcomponents according to Table 5. The ratio of clomazone and dipropylene glycoldibenzoate of Sample 5 was approximately 1:6. The eye irritation of Sample 5 wascompared with that of Control 5 (without the addition of dipropylene glycoldibenzoate).
Table 5
Example 6
Emulsion concentrate compositions Sample 6 and Control 6 were prepared withcomponents according to Table 6 below. The ratio of pyriproxyfen and dipropyleneglycol dibenzoate of Sample 6 was approximately 1:5. The eye irritation of Sample 6was compared with that of Control 6 (without the addition of dipropylene glycoldibenzoate).
Table 6
Example 7
Emulsion concentrate compositions Sample 7 and Control 7 were prepared withcomponents as set out in Table 7 below. The ratio of pyriproxyfen and diethyleneglycol dibenzoate of Sample 7 was approximately 1:10. The eye irritation of Sample7 was compared with that of Control 7 (without the addition of diethylene glycoldibenzoate).
Table 7
Example 8
Emulsion concentrate compositions Sample 8 and Control 8 were prepared withcomponents according to Table 8 below. The ratio of pyriproxyfen and dipropyleneglycol dibenzoate of Sample 7 was approximately 1:16. The eye irritation of Sample8 was compared with that of Control 8 (without the addition of dipropylene glycoldibenzoate).
Table 8
Example 9
Emulsion concentrate compositions Sample 9 and Control 9 were preparedaccording to the recipe of Table 9. The ratio of pyriproxyfen and dipropylene glycoldibenzoate of Sample 9 was approximately 1:20. Eye irritation of Sample 9 was
compared with that of Control 9 (without the addition of dipropylene glycoldibenzoate).
Table 9
Example 10
Emulsion concentrate compositions Sample 10 and Control 10 were preparedaccording to the recipe of Table 10 below. The ratio of lufenuron and dipropyleneglycol dibenzoate of Sample 10 was approximately 1:30. The eye irritation ofSample 10 was compared with that of Control 10 (without the addition of dipropyleneglycol dibenzoate).
Table 10
Example 11
Emulsion concentrate compositions Sample 11 and Control 11 were preparedaccording to the recipe of Table 11. The ratio of abmectin and dipropylene glycoldibenzoate of Sample 11 was approximately 1:90. The eye irritation of Sample 11was compared with that of Control 11 (without the addition of dipropylene glycoldibenzoate).
Table 11
Example 12
Emulsion concentrate compositions Sample 12 and Control 12 were preparedaccording to the recipe of Table 12. The ratio between bifenthrin and the combineddipropylene glycol dibenzoate and diethylene glycol dibenzoate of Sample 12 wasapproximately 1:5. The eye irritation of Sample 12 was compared with that ofControl 12 (without the addition of dipropylene glycol dibenzoate and diethylene glycoldibenzoate).
Table 12
Example 13
The eye irritation potential of the compositions of the Samples and Controls ofExamples 1 to 12 was determined as described above. The performance of thecompositions of the Samples and Controls was categorized as follows:
Category 0 (Cat 0): strongly irritant
Category I (Cat I): irritant
Category II (Cat II): moderate irritant
Category III (Cat III): non-irritant
The results are listed in Table 13 below.
Table 13
From the results set out in Table 13, it can be seen that dipropylene glycoldibenzoate and diethylene glycol dibenzoate, whether used alone or in combination,were very effective in significantly reducing the eye irritation potential of thecompositions.

Claims (18)

1. An emulsifiable concentrate (EC) agrochemical composition comprising at leastone dipropylene/diethylene glycol dibenzoate, at least one active ingredient and atleast one emulsifier, wherein the active ingredient comprises a compound selectedfrom pyripoxyfen, clomazone, a pyrethroid ester, a cyclohexime oxime, abenzoylphenylurea chitin synthesis inhibitor, and an avermectin.
2. The composition according to claim 1, wherein the dipropylene/diethylene glycoldibenzoate is present in an amount of from 2% to 90% by weight of the composition.
3. The composition according to claim 2, wherein the dipropylene/diethylene glycoldibenzoate is present in an amount of from 10% to 80% by weight of the composition.
4. The composition according to claim 3, wherein the dipropylene/diethylene glycoldibenzoate is present in an amount of from 20% to 70% by weight of the composition.
5. The composition according to any preceding claim, wherein the weight ratio of theactive ingredient and dipropylene/diethylene glycol dibenzoate is from 1:1 to 1:90.
6. The composition according to claim 5, wherein the weight ratio of the activeingredient and dipropylene/diethylene glycol dibenzoate is from 1:1 to 1:50.
7. The composition according to claim 6, wherein the weight ratio of the activeingredient and dipropylene/diethylene glycol dibenzoate is from 1:2 to 1:20.
8. The composition according to claim 7, wherein the weight ratio of the activeingredient and dipropylene/diethylene glycol dibenzoate is from 1:3 to 1:15.
9. The composition according to any preceding claim, wherein the active ingredientcomprises a compound selected from bifenthrin, pyriproxyfen, clethodim, clomazone,abamectin and lufenuron.
10. The composition according to any preceding claim, wherein the emulsifiercomprises a non-ionic emulsifier.
11. The composition according to claim 10, wherein the non-ionic emulsifier isselected from an alcohol alkoxylate, an alkylphenol ethoxylate, an alkylpolysaccharide,an amine ethoxylate, a castor oil ethoxylate, a sorbitan fatty acid ester ethoxylate anda polyoxyethylene fatty acid.
12. The composition according to any preceding claim, wherein the emulsifiercomprises an anionic emulsifier.
13. The composition according to claim 12, wherein the anionic emulsifier is selectedfrom an amine alkylbenzenesulfonate, an ammonium dodecylbenzene sulfonate, acalcium alkylsulphonate and a calcium alkylbenzenesulfonate.
14. The composition according to any preceding claim, wherein the emulsifiercomprises a cationic emulsifier.
15. The composition according to claim 14, wherein the cationic emulsifier is selectedfrom polyoxyethylene quaternary and polyoxyethylene tallow ethylmonium ethosulfate,stearyltrimethylammonium chloride and benzyl bis(2-chloroethyl)ethylammoniumbromide.
16. The composition according to any preceding claim, wherein the at least onedipropylene/diethylene glycol dibenzoate is diethylene glycol dibenzoate ordipropylene glycol dibenzoate.
17. The composition according to any of claims 1 to 15, wherein the at least onedipropylene/diethylene glycol dibenzoate comprises a mixture of diethylene glycoldibenzoate and dipropylene glycol dibenzoate.
18. A method of treating pests at a locus comprising applying to the locus acomposition according to any of claims 1 to 17.
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