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DE2635100A1 - Herbicides contg. phenoxy-methyl-phenoxy-propionic acid derivs. - esp. useful for selective control of monocotyledonous plants - Google Patents

Herbicides contg. phenoxy-methyl-phenoxy-propionic acid derivs. - esp. useful for selective control of monocotyledonous plants

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Publication number
DE2635100A1
DE2635100A1 DE19762635100 DE2635100A DE2635100A1 DE 2635100 A1 DE2635100 A1 DE 2635100A1 DE 19762635100 DE19762635100 DE 19762635100 DE 2635100 A DE2635100 A DE 2635100A DE 2635100 A1 DE2635100 A1 DE 2635100A1
Authority
DE
Germany
Prior art keywords
opt
phenoxy
alkyl
formula
propionic acid
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.)
Withdrawn
Application number
DE19762635100
Other languages
German (de)
Inventor
Guenter Lauterbach
Gerbert Linden
Siegmund Dr Lust
Werner Dr Mehrhof
Erich Dr Schacht
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Agrar GmbH and Co KG
Original Assignee
Celamerck GmbH and Co KG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Celamerck GmbH and Co KG filed Critical Celamerck GmbH and Co KG
Priority to DE19762635100 priority Critical patent/DE2635100A1/en
Priority to US05/819,823 priority patent/US4169720A/en
Priority to CS503777A priority patent/CS198263B2/en
Priority to TR20098A priority patent/TR20098A/en
Priority to AT569077A priority patent/AT358865B/en
Priority to CH949977A priority patent/CH629361A5/en
Priority to DD7700200400A priority patent/DD132400A5/en
Priority to IL5263777A priority patent/IL52637A/en
Priority to PH20068A priority patent/PH13834A/en
Priority to GB32574/77A priority patent/GB1582538A/en
Priority to DK348577A priority patent/DK348577A/en
Priority to SU772511559A priority patent/SU702994A3/en
Priority to PL1977200041A priority patent/PL110799B1/en
Priority to NL7708577A priority patent/NL7708577A/en
Priority to CA283,962A priority patent/CA1104367A/en
Priority to NZ184824A priority patent/NZ184824A/en
Priority to LU77912A priority patent/LU77912A1/xx
Priority to JP9372177A priority patent/JPS5341429A/en
Priority to BE179878A priority patent/BE857444A/en
Priority to AU27577/77A priority patent/AU513237B2/en
Priority to BR7705124A priority patent/BR7705124A/en
Priority to ES461317A priority patent/ES461317A1/en
Priority to ZA00774687A priority patent/ZA774687B/en
Priority to FR7724073A priority patent/FR2392952A1/en
Priority to IE1636/77A priority patent/IE45329B1/en
Priority to SE7708900A priority patent/SE7708900L/en
Priority to EG46677A priority patent/EG12798A/en
Publication of DE2635100A1 publication Critical patent/DE2635100A1/en
Priority to ES467785A priority patent/ES467785A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; 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
    • 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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N47/20—N-Aryl derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

(A) Herbicidal compsns. contain as active ingredient an ether of formula (I) In the formula R1 and R2 = H Cl or F. r3 = CH2OH, CH2OCONHR5, COOH, COOKat, COOR6, CONR7R8 or COSkg. Kat is an equivalent of an inorganic or organic cation. R4 = H, opt. branched 1-10C alkyl. R5 = opt. branched 1-4C alkyl or opt. halogenated phenyl. R6 = opt. branched 1-10C alkyl opt. substd. by Cl, OH, alkoxy, alkoxyalkoxy, alkylthio, NH2 (opt. mono- or dialkyl substd.) allyloxy or phenoxy; or it is phenyl, benzyl (opt. mono- or di-chlorosubstd.), cyclohexyl (opt. 1-ethynyl substd.), alkenyl, alkynyl, -N=C(CH3)2, 2-(2,4,5-trichlorophenoxy)ethyl, 2-(2,5-dichloro-4-bromophenoxy)-ethyl or a gp. of formula R7 = H, alkyl, hydroxyalkyl, alkenyl, alkynyl or phenyl opt. substd. by Cl, OH, NH2, phenylamino, thiazolyl or CH3O. R8 = H, alkyl, alkenyl or hydroxyalkyl. R9 = H, or 1-10C alkyl. n = 2-6 (All unspecified alkyl, alkenyl and alkynyl have 1-4C). Some (I) are already known as hypochloresterolaemics. They are now found to be useful for apre- or post-emergence herbicides esp. for selective control of monocotyledons at 0.1-3, esp. 0.3-1.5 kg/ha. They can be formulated with another herbicide, mainly active against dicotyledons, and opt. an antidote.

Description

Herbizide Mittel Herbicidal agents

Die Erfindung betrifft herbizide Mittel, die als Wirkstoff eine Verbindung der Formel enthalten.The invention relates to herbicidal compositions which, as active ingredient, contain a compound of the formula contain.

In der Formel I und im folgenden bedeutet R1 Wasserstoff, Fluor, Chlor,Brom, Jod, R2 Wasserstoff, Fluor, Chlor, Brom, Jod, R3 eine der Gruppen -OR oder -OMe, R Wasserstoff oder einen geradkettigen oder verzweigten Alkylrest mit 1 bis 10 Kohlenstoffatomen, der auch niederalkoxy- bzw. niederalkoxyniederalkoxy-substituiert sein kann, Me ein Äquivalent eines Kations.In formula I and in the following, R1 denotes hydrogen, fluorine, chlorine, bromine, Iodine, R2 hydrogen, fluorine, chlorine, bromine, iodine, R3 one of the groups -OR or -OMe, R is hydrogen or a straight-chain or branched alkyl radical with 1 to 10 carbon atoms, which can also be lower alkoxy or lower alkoxy lower alkoxy substituted, Me an equivalent of a cation.

Hervorzuheben sind diejenigen Verbindungen der Formel I, in denen sich der Substituent R1 in der 4-Position, der Substituent R2 gegebenenfalls in der 2-Position befindet.To be emphasized are those compounds of the formula I in which the substituent R1 is in the 4-position, the substituent R2 optionally in is in the 2 position.

Rl bedeutet vorzugsweise Chlor, R2 vorzugsweise Wasserstoff oder Chlor. Die Alkylreste R enthalten bevorzugt 1 bis 4 Kohlenstoffatome, z.B. Methyl, Äthyl, Isopropyl, n-Butyl.R1 preferably denotes chlorine, R2 preferably denotes hydrogen or chlorine. The alkyl radicals R preferably contain 1 to 4 carbon atoms, e.g. methyl, ethyl, Isopropyl, n-butyl.

Die Kationen Me können sich von anorganischen oder organischen Basen ableiten, insbesondere von Alkalibasen, z.B. NaOH, KOH, und von Ammoniak bzw Aminen, die ein, zwei oder drei Alkylreste bzw. substituierte Alkylreste enthalten, z.B. Methylamine, Äthylamine, Butylamine, Äthanolamine, gemischt substituierte Alkylamine, Benzylamin, Allylamin, Morpholin, Piperidin, Cyclohexylamin.The cations Me can be derived from inorganic or organic bases derive, in particular from alkali bases, e.g. NaOH, KOH, and from ammonia or amines, containing one, two or three alkyl radicals or substituted alkyl radicals, e.g. Methylamines, ethylamines, butylamines, ethanolamines, mixed substituted alkylamines, Benzylamine, allylamine, morpholine, piperidine, cyclohexylamine.

Typische Vertreter der erfindungsgemäßen Wirkstoffklasse sind z.B.Typical representatives of the class of active ingredients according to the invention are e.g.

2-(4-Phenoxymethylphenoxy)-propionsäure, 2-[4-(4-Chlorphenoxymethyl)-phenoxy]-propionsäure, Fp. 156-158°C, 2-[4-( 2,'4-Dichlorphenoxymethyl)-phenoxyi-propionsäure, Fp. 122-1230C, 2-[4-(2,4-Dichlorphenoxymethyl)-phenoxy].propionsäuremethylester, Fp. 640C, 2-[4-(4-Chlorphenoxymethyl)-phenoxy]-propionsäuremethylester, Fp. 70 - 710C, 2-C4-(4-Chlorphenoxymethyl) phenoxyl-propionsäure-nbutoxyäthylester, 2-[4-(2,4-Dichlorphenoxymethyl)-phenoxy]-propionsäureisopropylester, 2-E4-(4-Fluorphenoxymethyl)-phenoxy]-propionsäure, Fp. 143-144VC 2-[4-(4-Fluorphenoxymethyl)-phenoxy]-propionsäure-äthylester, 2-[4-(4-Bromphenoxymethyl)-phenoxy]-propionsäure, 2-[4-(4-Bromphenoxymethyl)-phenoxy]-propionsaure-butylester, 2-[4-(2-Chlor-4-bromphenoxymethyl)-phenoxy]-propionsäure, 2-[4-(2-Chlorphenoxymethyl)-phenoxy]-propionsäure-Diäthanolaminsalz, 2-[4-( 2, 4-Dichlorphenoxymethyl ) -phenoxy ] -propionsäure-Triäthanolaminsalz, 2-E4-(4-Fluorphenoxymethyl)-phenoxy]-propionsäure-Dimethylaminsalz, 2-[4-(2-Chlorphenoxymethyl)-phenoxy]-propionsäure-Natriumsalz, 2-[4-(2,4-Dichlorphenoxymethyl)-phenoxy]-propionsäure-Kaliumsalz.2- (4-phenoxymethylphenoxy) propionic acid, 2- [4- (4-chlorophenoxymethyl) phenoxy] propionic acid, Mp. 156-158 ° C, 2- [4- (2,4-dichlorophenoxymethyl) -phenoxyi-propionic acid, m.p. 122-1230C, 2- [4- (2,4-dichlorophenoxymethyl) -phenoxy] .propionic acid methyl ester, m.p. 640C, 2- [4- (4-chlorophenoxymethyl) -phenoxy] -propionic acid methyl ester, Mp. 70-710C, 2-C4- (4-chlorophenoxymethyl) phenoxyl-propionic acid n-butoxyethyl ester, 2- [4- (2,4-dichlorophenoxymethyl) -phenoxy] -propionic acid isopropyl ester, 2-E4- (4-fluorophenoxymethyl) -phenoxy] -propionic acid, M.p. 143-144VC Ethyl 2- [4- (4-fluorophenoxymethyl) phenoxy] propionate, 2- [4- (4-bromophenoxymethyl) -phenoxy] -propionic acid, 2- [4- (4-bromophenoxymethyl) -phenoxy] -propionic acid-butyl ester, 2- [4- (2-chloro-4-bromophenoxymethyl) phenoxy] propionic acid, 2- [4- (2-chlorophenoxymethyl) phenoxy] propionic acid diethanolamine salt, 2- [4- (2, 4-dichlorophenoxymethyl) phenoxy] propionic acid triethanolamine salt, 2-E4- (4-fluorophenoxymethyl) phenoxy] propionic acid dimethylamine salt, 2- [4- (2-chlorophenoxymethyl) phenoxy] propionic acid sodium salt, 2- [4- (2,4-dichlorophenoxymethyl) phenoxy] propionic acid potassium salt.

Die Verbindungen der Formel I sind z.T. aus der deutschen Offenlegungsschrift 2 342 118 bekannt. Die bisher nicht beschriebenen Verbindungen können analog den in der Offenlegungsschrift angegebenen Verfahren erhalten werden.Some of the compounds of the formula I are from the German Offenlegungsschrift 2,342,118 known. The connections not previously described can be analogous to the in the laid-open specification can be obtained.

Nach der erwähnten Offenlegungsschrift zeichnen sich die dort beschriebenen Verbindungen durch wertvolle pharmakologische Eigenschaften aus, z.B. durch cholesterinsenkende Wirkung.According to the aforementioned laid-open specification, those described there stand out Compounds have valuable pharmacological properties, e.g. cholesterol-lowering Effect.

Wie nun gefunden wurde, zeigen die Verbindungen der Formel I Uberraschenderweise auch eine starke selektive herbizide Wirkung gegen Ungräser, z.B. Ackerfuchsschwanz, Flughafer, Raygras, Wildhirsen. Die Selektivität ist so ausgeprägt, daß auch bei höheren Aufwandmengen Dikotyle allenfalls geringzügig geschädigt werden. Selbst in einigen Kulturen von monokotylen Nutzpflanzen, z.B. Reis, Gerste, Hafer, Weizen, können mit den erfindungsgemäßen Wirkstoffen Ungräser bekämpft werden.As has now been found, the compounds of the formula I surprisingly show also has a strong, selective herbicidal effect against grass weeds, e.g. foxtail, Wild oats, ryegrass, wild millet. The selectivity is so pronounced that even with higher amounts of dicots may only be slightly damaged. Self in some crops of monocotyledonous crops, e.g. rice, barley, oats, wheat, grass weeds can be combated with the active ingredients according to the invention.

Die neuen Mittel eignen sich fUr die Anwendung im Vorauflauf - wie auch im Nachauflaufverfahren, wobei die Aufwandmenge 0,1 bis 3 kg, vorzugsweise 0,3. bis l,5 kg/ha beträgt.The new means are suitable for pre-emergence use - such as also by the post-emergence method, the application rate being 0.1 to 3 kg, preferably 0.3. to 1.5 kg / ha.

Für die Anwendung werden die Verbindungen der Formel I in an sich bekannter Weise mit üblichen Hilfs- und/oder Trägerstoffen zu gebräuchlichen Formulierungen verarbeitet, z.B. zu Konzentraten, wie Emulsionskonzentraten oder Suspensionspulvern, bei denen der Wirkstoffgehalt zwischen etwa 10 und 95 Gewichtsprozent liegt, oder zu Stäuben, Emulsionen, Granulaten, Lösungen, die unmittelbar angewendet werden können und zwischen etwa 0,01 und 20 Gewichtsprozent Wirkstoff enthalten.For use, the compounds of the formula I are in per se in a known manner with customary auxiliaries and / or carriers to customary formulations processed, e.g. into concentrates such as emulsion concentrates or suspension powders, in which the active ingredient content is between about 10 and 95 percent by weight, or to dusts, emulsions, granules, solutions that are used immediately can and contain between about 0.01 and 20 percent by weight of active ingredient.

Die Konzentrate werden mit Wasser auf die gewünschte Anwendungskonzentration, im allgemeinen etwa 0,01 bis 3 Gewichtsprozent, verdünnt.The concentrates are mixed with water to the desired application concentration, generally about 0.01 to 3 percent by weight, diluted.

Formulierungsbeispiele 1. Suspensionspulver 25 Gew.-% 2-[4-(4-Fluorphenoxymethyl)-phenoxy]-propionsäure 55 Gew.-% Kaolin 10 Gew.-% kolloidale Kieselsäure 9 Gew. -% Calciumligninsulfonat (Dispergiermittel) 1 Gew. -, Natriumtetrapropylenbenzolsulfonat (Netzmittel) Die Bestandteile werden vermahlen und das Mittel wird für die Anwendung in Wasser so suspendiert, daß eine Wirkstoffkonzentration von etwa 0,01 bis 3% erhalten wird.Formulation Examples 1. Suspension powder 25% by weight of 2- [4- (4-fluorophenoxymethyl) phenoxy] propionic acid 55% by weight kaolin 10% by weight colloidal silica 9% by weight calcium lignosulfonate (Dispersant) 1 wt., Sodium tetrapropylene benzene sulfonate (wetting agent) Die Ingredients are ground and the agent is made for use in water suspended so that an active ingredient concentration of about 0.01 to 3% is obtained.

2. Stäubemittel 1 Gew. -% Natri um-2-[4-(4-Chlorphenoxymethyl )-phenoxy]-propionat 98 Gew.-% Talkum 1 Gew.-% Methylcellulose Die Bestandteile werden zur Herstellung des Stäubemittels homogen vermahlen.2. Dust 1% by weight sodium 2- [4- (4-chlorophenoxymethyl) phenoxy] propionate 98% by weight talc 1% by weight methyl cellulose The ingredients are used for manufacture grind the dust homogeneously.

3. Emulsionskonzentrat 20 Gew. -% Gew.-% 2-[4-(2,4-Dichlorphenoxy)-phenoxy]-propionsäurei sopropyle ster 70 Gew.-% flüssiges Lösungsmittelgemisch aus hochsiedenden aromatischen Kohlenwasserstoffen (Shellsol A) 6,5 Gew.-% Tensiofix AS (Emulgator) 3,5 Gew.-% Tensiofix DS (Emulgator) Aus den Bestandteilen wird in üblicher Weise ein Emulsionskonzentrat bereitet.3. Emulsion concentrate 20% by weight% by weight 2- [4- (2,4-dichlorophenoxy) phenoxy] propionic acid sopropyle ster 70 wt .-% liquid solvent mixture of high-boiling aromatic Hydrocarbons (Shellsol A) 6.5% by weight Tensiofix AS (emulsifier) 3.5% by weight Tensiofix DS (emulsifier) The ingredients are converted into an emulsion concentrate in the usual way prepares.

In dem nachstehenden Herstellungsbeispiel wird die Herstellung einiger charakteristischer neuer Verbindungen der Formel I beschrieben.In the following manufacturing example, the manufacture of some characteristic new compounds of formula I described.

Herstellungsbeispiel a) Man löst 2,3 g Natrium in 100 ml absolutem Äthanol, gibt 26,9 g 4-(2,4-Dichlorphenoxymethyl)-phenol und 16.7 g 2-Brompropionsäuremethylester hinzu, kocht drei Stunden und dampft ein. Nach üblicher Aufarbeitung mit Wasser und Chloroform erhält man 2-[4-(2,4-Dichlorphenoxymethyl)-phenoxy]-propionsäuremethylester, Fp. 640C; Ausbeute 80 % d.Th..Preparation example a) 2.3 g of sodium are dissolved in 100 ml of absolute Ethanol, gives 26.9 g of 4- (2,4-dichlorophenoxymethyl) phenol and 16.7 g of methyl 2-bromopropionate added, boiled for three hours and evaporated. After the usual work-up with water and chloroform, methyl 2- [4- (2,4-dichlorophenoxymethyl) phenoxy] propionate is obtained, M.p. 640C; Yield 80% of theory.

b) 10 2-[4-(2,4-Dichlorphenoxymethyl)-phenoxy-propionsäuremethylester werden mit 10 KOH in 100 ml Äthanol zwei Stunden gekocht. Man dampft ein, löst in Wasser, wäscht mit Äther und säuert mit Salzsäure an, wobei 2-[4-(2,4-Dichlorphenoxy-methyl)-phenoxy]-propionsäure ausfällt, Fp. 122-1230C; Ausbeute 90 % d.Th..b) 10 methyl 2- [4- (2,4-dichlorophenoxymethyl) phenoxy propionate are boiled with 10 KOH in 100 ml of ethanol for two hours. One evaporates, dissolves in Water, washed with ether and acidified with hydrochloric acid, with 2- [4- (2,4-dichlorophenoxy-methyl) -phenoxy] -propionic acid precipitates, m.p. 122-1230C; Yield 90% of theory.

Claims (4)

Patentansprüche 1. Herbizide Mittel, gekennzeichnet durch einen Gehalt an einer Verbindung der Formel worin R1 Wasserstoff, Fluor, Chlor, Brom oder Jod, R2 Wasserstoff, Fluor, Chlor, Brom oder Jod, R3 eine der Gruppen -OR oder OMe, R Wasserstoff oder einen geradkettigen oder verzweigten Alkylrest mit 1 bis 10 Kohlenstoffatomen, der auch niederalkoxy- bzw. niederalkoxyniederalkoxysubstituiert sein kann, Me ein Äquivalent eines Kations bedeutet.Claims 1. Herbicidal agents, characterized in that they contain a compound of the formula where R1 is hydrogen, fluorine, chlorine, bromine or iodine, R2 is hydrogen, fluorine, chlorine, bromine or iodine, R3 is one of the groups -OR or OMe, R is hydrogen or a straight-chain or branched alkyl radical with 1 to 10 carbon atoms, which is also lower alkoxy or lower alkoxy-lower alkoxy, Me is an equivalent of a cation. 2. Verwendung von Verbindungen der Formel 1 zur Bekämpfung von Ungräsern.2. Use of compounds of formula 1 for combating grass weeds. (g.jVerbindungen der Formel worin R1 und R3 die oben angegebene Bedeutung haben und R2 für Fluor, Chlor, Brom oder Jod steht.(g.jCompounds of the formula in which R1 and R3 have the meaning given above and R2 represents fluorine, chlorine, bromine or iodine. 4. Verfahren zur Herstellung von herbiziden Mitteln nach Anspruch 1, dadurch gekenn7eichnet, daß man einen Wirkstoff der Formel I mit üblichen Hilfs- und/oder Trägerstoffen zu gebräuchlichen Formulierungen, insbesondere zu Suspensionspulvern, Stäuben, Emulsionskonzentraten, Granulaten, Sprays oder Lösungen, verarbeitet.4. Process for the preparation of herbicidal compositions according to claim 1, characterized in that an active ingredient of the formula I is used with conventional auxiliaries and / or carriers for common formulations, in particular for suspension powders, Dusts, emulsion concentrates, granules, sprays or solutions.
DE19762635100 1976-08-04 1976-08-04 Herbicides contg. phenoxy-methyl-phenoxy-propionic acid derivs. - esp. useful for selective control of monocotyledonous plants Withdrawn DE2635100A1 (en)

Priority Applications (28)

Application Number Priority Date Filing Date Title
DE19762635100 DE2635100A1 (en) 1976-08-04 1976-08-04 Herbicides contg. phenoxy-methyl-phenoxy-propionic acid derivs. - esp. useful for selective control of monocotyledonous plants
US05/819,823 US4169720A (en) 1976-08-04 1977-07-28 2-[4-(4-Chlorophenoxymethyl)-phenoxy]-propionic acid compounds as herbicides
CS503777A CS198263B2 (en) 1976-08-04 1977-07-29 Herbicide
TR20098A TR20098A (en) 1976-08-04 1977-08-02 HERBISID COMPOUNDS AND COMPOSITIONS AND MANUFACTURES
AT569077A AT358865B (en) 1976-08-04 1977-08-02 HERBICIDAL AGENTS
CH949977A CH629361A5 (en) 1976-08-04 1977-08-02 HERBICIDAL AGENTS.
DD7700200400A DD132400A5 (en) 1976-08-04 1977-08-02 HERBICIDE MEDIUM
IL5263777A IL52637A (en) 1976-08-04 1977-08-02 Herbicidal method and compositions containing(phenoxymethyl)phenoxypropanols,their corresponding carboxylic acids and their derivatives,certain such novel compounds and their preparation
PH20068A PH13834A (en) 1976-08-04 1977-08-02 2-(4(-chlorophenoxy methyl)phenoxy)-propionic acid compounds as herbicides
NL7708577A NL7708577A (en) 1976-08-04 1977-08-03 Herbicides contg. phenoxy-methyl-phenoxy-propionic acid derivs. - esp. useful for selective control of monocotyledonous plants
BR7705124A BR7705124A (en) 1976-08-04 1977-08-03 HERBICIDE COMPOSITION, COMPOUNDS, PROCESS TO COMBAT UNWANTED PLANTS IN USEFUL CULTURES, PROCESS TO PREPARE SUCH COMPOSITION, AND PROCESS TO PREPARE COMPOUNDS
SU772511559A SU702994A3 (en) 1976-08-04 1977-08-03 Herbicide agent
PL1977200041A PL110799B1 (en) 1976-08-04 1977-08-03 Herbicide
GB32574/77A GB1582538A (en) 1976-08-04 1977-08-03 Method of controlling plant growth phenylbenzyl ether derivatives and herbicidal uses thereof
CA283,962A CA1104367A (en) 1976-08-04 1977-08-03 Herbicidal compositions containing 4-(phenoxymethyl)- phenoxypropionic acid derivatives
NZ184824A NZ184824A (en) 1976-08-04 1977-08-03 Method of controlling plant growth with and compositions containing phenoxymethylphenoxy compounds and certain of these compounds
LU77912A LU77912A1 (en) 1976-08-04 1977-08-03
JP9372177A JPS5341429A (en) 1976-08-04 1977-08-03 Weed killer compound and composition and their production
BE179878A BE857444A (en) 1976-08-04 1977-08-03 HERBICIDE COMPOUNDS, HERBICIDAL AGENTS CONTAINING THEM AND THEIR PREPARATION
AU27577/77A AU513237B2 (en) 1976-08-04 1977-08-03 Method of controlling plant growth
DK348577A DK348577A (en) 1976-08-04 1977-08-03 HERBICIDE COMPOUNDS AND MEDICINES AND THEIR PREPARATION
ES461317A ES461317A1 (en) 1976-08-04 1977-08-03 2-{8 4-(4-Chlorophenoxymethyl)-phenoxy{9 -propionic acid compounds as herbicides
ZA00774687A ZA774687B (en) 1976-08-04 1977-08-03 Herbicidal compounds and preparations
FR7724073A FR2392952A1 (en) 1976-08-04 1977-08-04 HERBICIDE COMPOUNDS, HERBICIDAL AGENTS CONTAINING THEM AND THEIR PREPARATION
IE1636/77A IE45329B1 (en) 1976-08-04 1977-08-04 Phenylbenzyl ether derivatives and herbicidal uses thereof
SE7708900A SE7708900L (en) 1976-08-04 1977-08-04 HERBICIDA ASSOCIATIONS AND MEDICINES AND THEIR PREPARATION
EG46677A EG12798A (en) 1976-08-04 1977-08-06 Herbicidal compounds and agents as well as their production
ES467785A ES467785A1 (en) 1976-08-04 1978-03-11 2-{8 4-(4-Chlorophenoxymethyl)-phenoxy{9 -propionic acid compounds as herbicides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19762635100 DE2635100A1 (en) 1976-08-04 1976-08-04 Herbicides contg. phenoxy-methyl-phenoxy-propionic acid derivs. - esp. useful for selective control of monocotyledonous plants

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DE2635100A1 true DE2635100A1 (en) 1978-02-09

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4710315A (en) * 1984-04-16 1987-12-01 Merck Patent Gesellschaft Mit Beschrankter Haftung Anisotropic compounds and liquid crystal mixtures therewith

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4710315A (en) * 1984-04-16 1987-12-01 Merck Patent Gesellschaft Mit Beschrankter Haftung Anisotropic compounds and liquid crystal mixtures therewith
USRE36849E (en) * 1984-04-16 2000-09-05 Merck Patent Gmbh Anisotropic compounds and liquid crystal mixtures therewith

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ZA774687B (en) 1979-04-25

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