CA2072104A1 - Selective herbicides - Google Patents

Selective herbicides

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Publication number
CA2072104A1
CA2072104A1 CA 2072104 CA2072104A CA2072104A1 CA 2072104 A1 CA2072104 A1 CA 2072104A1 CA 2072104 CA2072104 CA 2072104 CA 2072104 A CA2072104 A CA 2072104A CA 2072104 A1 CA2072104 A1 CA 2072104A1
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CA
Canada
Prior art keywords
weight
agent
component
acid esters
phenoxy
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.)
Abandoned
Application number
CA 2072104
Other languages
French (fr)
Inventor
Rudolf Heinrich
Thomas Maier
Hans Schumacher
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.)
Hoechst AG
Original Assignee
Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2072104A1 publication Critical patent/CA2072104A1/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-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
    • 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
    • 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
    • A01N25/22—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 ingredients stabilising the active ingredients
    • 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
    • A01N43/34—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
    • A01N43/74—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
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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

Landscapes

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

Abstract

Abstract of the disclosure:
Selective herbicidal agents The agents according to the invention are stable formula-tions based on emulsion concentrates and contain a) one or more herbicidal phenoxyphenoxy- or heteroaryl-oxy-phenoxy-carboxylic acid esters, b) one or more compounds from the group comprising optionally substituted 1-aryl-3-alkoxycarbonyl-5-alkyl-1,2,4-triazoles, c) one or more carboxylic acid esters or phosphoric acid esters of aliphatic mono- di- or polyalcohols as a stabilizing agent, d) one or more organic solvents, in particular, with a predominant content of aromatic solvents, and e) one or more emulsifiers and if appropriate wetting agents and customary additives.

Description

20721~
HOECHST AKTIENGESELLSCHAFT Dr.WE/gm HOE 89/F 352 Description Selective herbicidal agents The invention xelates to novel liquid ~elective herbi-cidal agents which contain active compound6 from the group comprising phenoxy herbicide~ and optionally substituted 1-aryl-3-alkoxycarbonyl-5-alkyl-1,2,4-tri-azoles in the form of emulsion concentrates which are stable chemically and during use.

It is known that compounds from the group comprising phenoxy-phenoxy herbicides and benzoxazolyloxy-phenoxy herbicides can be combined with other compounds having a selective herbicidal action or with agents which protect crop plants (safeners) for the purpose of optimizing the action spectrum to give finished formulations which are stable chemically and during use.

It is known, inter alia, from European Patent A-0,174,562 (US Patent A-4,639,266) that benzoxazolyloxy-phenoxy herbicides, such as, for example, ethyl 2-(4-(6-chloro-2-benzoxazolylox~)-phenoxy-propionate (sic) (fenoxaprop-ethyl) can be combined with safeners from the group comprising optionally substituted 1-aryl-3-alkoxy carbonyl-5-alkyl-1,2,4-triazole compounds by adding corresponding amounts of a formulation of the 1,2,4-triazole mentioned to the spray liquor shortly beforeapplication of the fenoxapropethyl, 80 that the advantag-eous biological properties of the combin~tion of the two active compounds can be utilized in this manner. However, this process is cumbersome and time-consuming, and can easily lead to incorrect dosages in practice.

There was thus the ob~ect of avoiding the~e difficulties and of preparing ~iologically active homogeneous formula-tions of these two active compounds which are stable chemically and during use and which meet the requirements 20721~

imposed in practice.

It was to be remembered in particular that the two classes of active compound can have an adverse influence on each other in the presence of customary formulation S auxiliaries and stabilizers at elevated storage tempera-tures and then undergo noticeable chemical changes, especially over prolonged storage times, and lead to components which are biologically less active or even inactive. These disadvantages are overcome by the present invention.

The present invention relates to liquid selective herbicidal agents based on emulsion concentrate~, which contain a) one or more herbicidal phenoxyphenoxy- or heteroaryl-oxy-phenoxy-carboxylic acid esters~

b) one or more compounds from the group comprising optionally substituted l-aryl-3-alkoxycarbonyl-5-alkyl-1,2,4-triazoles, c) one or more carboxylic acid esters or phosphoric acid esters of aliphatic mono- di- or polyalcohols as a stabilizing agent, d) one or more organic solvents, in particular with a predominant content of aromatic solvent~, and e) one or more emulsifiers and if appropriate wetting agents and customary additive~.

The herbicidal phenoxy- or heteroaryloxy-phenoxy-carboxylic acid esters which can be employed (component a) are, for example, the known optionally substituted phenoxyphenoxy-, quinoxalyloxyphenoxy-, pyridyloxy-phenoxy-, benzoxazolyloxyphenoxy- or benzothiazolyloxy-phenoxy-carboxylic acid esters, in the form of the pure 2~7210~

optical isomers or as isomer mixtures (for example racemates). The compounds are described, for example, in DE-A 2,136,828 (US-A 4,238,626); DE-A 2,223,894 (US-A
3,954,442); British Patent 2,0432,539 ( 8iC ); British Patent 1,599,121; and DE-A 2,640,730 (US-A 4,130,413).
The (C1-C4)alkyl, (C2-C~)alkenyl or ( C3-C4 )alkynyl ester~
are particularly suitable.

Suitable herbicides of component a) are, for example, the active compounds methyl 2-(4-(2,4-dichlorophenoxy)-phenoxy)-propionate (diclofop-methyl), methyl 2-(4-(4-bromo-2-chlorophenoxy)-phenoxy)-propionate, methyl 2-(4-(4-trifluoromethylphenoxy)-phenoxy)-propionate, methyl 2-(4-(2-chloro-4-trifluoromethylphenoxy)-phenoxy)-propionate, ethyl 4-(4-(4-trifluoromethylphenoxy)-phenoxy)-pent-2-enoate, ethyl 2-(4-(3,5-dichloropyridyl-2-oxy)-phenoxy)-propionate, methyl or 2-ethoxyethyl2-(4-(3-chloro-5-trifluoromethyl-pyridyl-2-oxy)-phenoxypropionate (haloxyfop-methyl or haloxyfop-2-ethoxy-ethyl), propargyl 2-(4-(3,5-dichloropyridyl-2-oxy)-phenoxy)-propionate, ethyl 2-(4-(6-chlorobenzoxazol-2-yl-oxy)-phenoxy)-propionate (fenoxaprop-ethyl), 2072~04 ethyl 2-(4-(6-chlorobenzothiazol-2-yl-oxy)-pheno~y)-propionate (fenthiaprop-ethyl~, methyl 2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-phenoxy)-propionate, butyl 2-(4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy-propionate (sic) (fluazifop-butyl), ethyl 2-(4-(6-chloro-2-quinoxalyloxy)-phenoxy-propionate (sic) (quizalofop-ethyl) and ethyl 2-(4-(6-fluoro-2-quinoxalyloxy)-phenoxy)-propionate.

The active compounds mentioned in the D,L- or in particu-lar the enxiched or pure D-form are preferred.

Agents according to the invention containing the herbi-cidal active compound diclofop-methyl or fenoxaprop-ethyl are particularly preferred. Most of the abovementioned active compounds are also described in "The Pesticide Manual", 8th edition 1987, British Crop. Protection Council.

Suitable compounds for component b) of the agents accord-ing to the invention are the compounds mentioned in European Patent A-0,174,562, preferably the 1-(2,4-dichlorophenyl)-3-(C,-C4-alkoxy)carbonyl-5-halogenoalkyl-1,2,4~triazole compounds, in particular the 1-(2,4-dichlorophenyl)-3-ethoxycarbonyl-5-halogenoalkyl-1,2,4-triazoles, in which the halogenoalkyl radical is prefer-ably CCl3, CHCl2 or CHF2CF2.

Low molecular weight esters of carboxylic acids or phosphoric acid~ with alcohols, diols or polyols, for example e6ters of aliphatic C2-C5-carboxylic acids or phosphoric acid and linear or branched aliphatic C2-C12-alcohols, -diols or polyols, are of particular interest 20721~

as component c) having a stabilizing action. Preferred compounds here are esters of carboxylic acid~, such as acetic acid, propionic acid, butanoic acid or pentanoic acid, in particular acetic acid, or of orthophosphoric S acid with alcohols, such as methanol, ethanol, propanol, isopropanol, n~ , t- and 2-butanol, n-, i- or 2-pentanol, n-, i- or 2-hexanol, heptanol, octanol, non-anol, decanol, undecanol and dodecanol, or diols, such as glycol, propanediol, butanediol and hexanediol, or polyols, such as glycerol, pentaerythritol and hexitol.

Particularly preferred compounds are phosphoric acid esters, such as tri-n-butyl phosphate, or esters of acetic acid with C2-C5-alcohols or with diols, such as l,4-butanediol, or with triols, such as glycerol, in particular the esters butyl acetate, pentyl acetate, hexyl acetate, heptyl acetate, nonyl acetate, 1,4-bis-(acetoxy)-butane and glycerol triacetate.

Organic solvents, such as aliphatic or aromatic hydro-carbons, aliphatic cyclic and acyclic ketones, N-methyl-pyrrolidone, dimethylformamide and alkylene glycol mono~and diesters or corresponding ethers, especially solvents having a high content of aromatics, are suitable, for example, as component d).

Examples of suitable aromatic solvents are toluene, xylenes, higher-boiling aromatic fractions and methyl-naphthalenes, and a particularly suitable ketone is cyclohexanone.

Customary emulsifiers, preferably one or more from the group comprising alkylbenzenesulfonates, such as calcium dodecylsulfonate, and fatty acid polyglycol esters, such as ethoxylated castor oil, are suitable as component e).
Any wetting agents contained in the agents are preferably tho~e from the group comprising alkylphenol polyglycol ethers and alkanol polyglycol ethers.

20721~

The ethoxylated castor oil or ethoxylated ricinic acid which can be employed according to the invention con-tains, in particular, 20 to 60 EO units (EO = ethylenoxy units). The products Emulsogen EL 400 or ~Emulsogen EL
360 (Hoechst AG), for example, can be employed. The fatty acid polyglycol esters contain, in paxticular, 12-18 carbon atoms in the fa~ty acid part. The ethoxylated alkylphenols are, in particular, nonylphenols and prefer-ably contain 20-200 EO. These include, for example, ~Arkopal N 100 (Hoechst AG). Ethoxylated (c~-c2o~alkanols having an EO content of 3 to 20 EO, for example ~Genapol X 060 ~Hoechst AG) may be mentioned as preferred alkanol polyglycol ethers. Of the emulsifiers and wetting agents mentioned, ethoxylated castor oil and the alkanol poly-glycol ethers are particularly suitable according to theinvention.

The herbicidal agents according to the invention can contain further customary additives for emulsion concen-trates, for example stabilizers against moisture, such as, for example, acid anhydrides, substituted amines and epoxide compounds, such as epoxidized linseed oil or soya oil.

The herbicidal agents according to the invention as a rule contain 5-50% by weight, preferably 20-35% by weight, of components a) and b), 2-20% by weight, in particular 5-15% by weight, of component c) and further-more 5-40~ by weight, preferably 10-25% by weight, of solvent and 10-30% by weight, pre~erably 15-25~ by weight, of emul~ifiers and wetting agents.

The ratio of the active compound components a) and b) to one another in the formulations is preferably 5:1 to 1:3.
The optimum amount of component c) depends on the amount of active compounds a) and b) and can easily be deter-mined in preliminaxy experiments.

The invention furthermore relates to a proce~s for the 20~2~04 preparation of the agents according to the invention. For this, the abovementioned components are mixed with one another in the required amounts at temperatures of preferably 10 to 60C, advantageously at room tempera-ture or slightly above, until a homogeneous solution ofthe individual component~ has formed.

For carrying out the process in practice, the solvent or solvent mixture is first initially introduced into a tank with a stirrer; the two active compound componentQ a) and b) are then added and the mixture is stirred until a clear solution is obtained. The compounds of component c) to be employed according to the invention are allowed to run slowly into this solution and the emulsifiers and if appropriate wetting agents and further additives are then added. The mixture is subsequently stirred until a clear solution is formed. The entire operation is advantage-ously carried out at room temperature or slightly above.
The sequence of addition of the components can also be different.

The emulsion concentrate prepared, which corresponds to a practically anhydrous solution of components a)l b), c) and e) in the organic solvent, is outstandingly stable towards chemical degradation of the active compounds and towards phase separations, such as, for example, the precipitation of components, even at comparatively high active compound contents. They therefore have a very good storage stability and are suitable for storage under climatically adverse conditions, in particular al80 at high temperatures o$ 30 to 50-C.

Before biological use of the emulsion concentrates, these are mixed with water to give emulsions which present no problems when used and which are not inferior in their activity to the combination~ of the active compounds a) and b), formulated if appropriate, prepared in the spray tank.

2072~

The following Examples are intended to illustrate the invention in more detail:

~xample 1 9.5% by weight of fenoxaprop-P-ethyl (I) (D-isomer of fenoxaprop-ethyl) are dissolved in 42% by weight of xylene at 25-30C, while stirring. 4.7~ by weight of 1-(2,4-dichlorophenyl)-3-ethoxycarbonyl-5-trichloromethyl-1,2,4-triazole (II) and then 12% by weight of a C12-Cl8-fatty alcohol polyglycol ether (containing 6 E0) and 6.8%
by weight of a Cl2-C18-fatty acid polyglycol ester (con-taining 40 E0) are added to the clear solution and the mixture is stirred until a clear solution is obtained.

5.0% by weight of epoxidized 80ya oil, 10.0% by weiqht of a xylene solution of the Ca salt of dodecylbenzene-sulfonic acid and 10% by weight of glycerol triacetateare added to this solution and the mixture is subse-quently stirred for 20 minutes.

A portion of the sample is stored at 50C for 3 month~
and then analyzed:

Content, Content after starting value 3 month~/50C
Compound I 9.2% by weight 9.1% by weight Compound II 4.6% by weight 4.6% by weight Comparison Example 1 25 The experiment from Example 1 is repeated, the same amount of xylene being added instead of 10% by weight of glycerol triacetate. The sample is likewise stored at 50C for 3 months and then analyzed.

Content, Content after starting value 3 months/50C
Compound I 9.2% by weight 8.6% by weight Compound II 4.6% by weight 3.3% by weight ~xa~ple 2 12.5% by weight of fenoxaprop-P-ethyl (I) (= D-isomer of fenoxaprop-ethyl) are dissolved in 35% by weight of xylene at 25-30C, while stirring. 8.8% by weight of 1-(2,4-dichlorophenyl)-3-ethoxycarbonyl-5-trichloromethyl-1,2,4-triazole (II) and then 10% by weight of a C12-Cl8-fatty acid polyglycol ether (containing 8 E0) and 8.7% hy weight of a C12-C1B-fatty acid polyglycol ester (containing 40 E0) are added to the clear solution and the mixture is stirred until a clear solution is obtained. 5% by weight of epoxidized linseed oil, 10.0% by weight of a xylene solution of the Ca salt of dodecylbenzenesulfonic acid and 10% by weight of tri-n-butyl phosphate are added to this solution and the mixture is subsequently stirred for about 20 minutes.

A portion of the sample is stored at 50C for 3 months and then analyzed:

Content, Content after starting value 3 months/50C
Compound I 11.8% by weight 11.7% by weight Compound II 8.2% by weight 8.2% by weight Compari~on Example 2 The experiment from Example 2 is repeated, but instead of the 10% by weight of tri-n-butyl phosphate the same amount of xylene is added. The sample i8 likewi~e stored at 50C for 3 months and then analyzed.

Content, Content aftsr starting value 3 months/50C
Compound I 11.6~ by weight 9.9% by weight Compound II 8.1~ by weight 6.5% by weight Example 3 16.5% by weight of fenthiaprop-ethyl (III) are dissolved in 42% by weight of xylene at 25-30C, while stirring.
8.2~ by weight of 1-(2,4-dichloro-phenyl)-3-ethoxy-carbonyl-5-trichloromethyl-1,2,4-triazole (II) and then 5% by weight of a Cl2-Cl8-fatty alcohol polyglycol ether (containing 10 E0) and 6.3% by weight of a C12-C1a-fatty acid polyglycol ester (containing 36 E0) are added to this clear solution and the mixture is stirred until a clear solution is obtained. 5% by weight of epoxidized linseed oil, 5% by weight of calcium dodecylbenzene-sulfonate and 12% by weight of hexyl acetate are added to this solution and the mixture is subsequently 3tirred for about 20 minutes.

A portion of the sample is stored at 50C for 3 months and then analyzed:

Content, Content after starting value 3 months/50C
Compound III 15.6% by weLght 15.4% by weight Compound II 7.7% by weight 7.6% by weight Comparison ~ample 3 The experiment from Example 3 is repeated, but in~tead of the 12% by weight of hexyl acetate the same amount of xylene is added. The sample is likewise 3tored at 50C
for 3 months and then analyzed.

2~721~4 Content, Content after starting value 3 months/50C
Compound I 15.5~ by weight 13.9% by weight Compound II 7.6~ by weight 6.0% by weight ~xample 4 The procedure is analogous to Example 1, but 1-(2,4-dichlorophenyl)-3-ethoxycarbonyl-5-dichloromethy~ 2~4-triazole is employed as the triazole compound. A compar-ably stable emulsion concentrate is obtained.

~xample 5 The procedure is analogous to Example 2, but 1-(2,4-dichlorophenyl)-3-ethoxycarbonyl-5-(1,1,2,2-tetrafluoro-ethyl)-1,2,4-triazole is employed as the triazole com-pound. The resulting emulsion concentrate is stable at 50C for 3 months and in particular exhibits no notice-able degradation of the active compound content.

Biological ~xamples The emulsion concentrates obtained according to the preparation examples are diluted to the use concentration with water and used against monocotyledon or dicotyledon or mono- and dicotyledon weeds in field experiments.

The biological studies show that there are no noticeable differences between the fini~hed formulations and the combinations of the individual active compounds prepared in the spray tank (tank mixture) either in plant toler-ance or in herbicidal action.

Claims (10)

Patent Claims:
1. A liquid herbicidal agent based on an emulsion concentrate, which contains a) one or more herbicidal phenoxyphenoxy- or hetero-aryloxy-phenoxy-carboxylic acid esters, b) one or more compounds from the group comprising optionally substituted 1-ary1-3-alkoxycarbonyl-5-alkyl-1,2,4-triazoles, c) one or more carboxylic acid esters or phosphoric acid esters of aliphatic mono- di- or polyalcohols as a stabilizing agent, d) one or more organic solvents, and e) one or more emulsifiers and if appropriate wetting agents and customary additives.
2. An agent as claimed in claim 1, which contains optionally substituted phenoxyphenoxy-, quinoxalyl-oxyphenoxy-, pyridyloxyphenoxy-, benzoxazolyloxy-phenoxy- or benzothiazolyloxyphenoxy-carboxylic acid esters as component a).
3. An agent as claimed in either of claims 1 or 2, which contains 1-(2,4-dichlorophenyl)-3-(C1-C4-alkoxy)-carbonyl-5-halogenoalkyl-1,2,4-trlazole compounds as component b).
4. An agent as claimed in any one of claims 1 to 3, which contains esters of C2-C5-carboxylic acids or phosphoric acid and linear or branched aliphatic C2-C12-alcohols, diols or polyols as component c).
5. An agent as claimed in any one of claims 1 to 4, which contains toluene, xylenes, higher-boiling aromatic fractions, methylnaphthalenes or cyclohexan-one as the solvent.
6. An agent as claimed in any one of claims 1 to 5, which contains customary emulsifiers and wetting agents from the group comprising alkylbenzene-sulfonates, fatty acid polyglycol esters and alkyl-phenol ethers and alkanol polyglycol ethers as component e).
7. An agent as claimed in any one of claims 1 to 6, which contains 5-50% by weight of components a) and b), 2-20% by weight of component c), 5-40% by weight of solvent and 10-30% by weight of emulsifiers and wetting agents.
8. An agent as claimed in claim 7, which contains 20-35% by weight of components a) and b), 5-15% by weight of component c), 10-25% by weight of solvent and 15-25% by weight of emulsifiers and wetting agents.
9. A process for the preparation of a herbicidal agent defined as claimed in any one of claims 1 to 8, which comprises mixing the components a) to e) at 10 to 60°C until a homogeneous solution of all the com-ponents has formed.
10. The use of an agent as claimed in any one of claims 1 to 8 for the preparation of an aqueous herbicidal emulsion.
CA 2072104 1989-10-28 1990-10-24 Selective herbicides Abandoned CA2072104A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19893935977 DE3935977A1 (en) 1989-10-28 1989-10-28 SELECTIVE HERBICIDES
DEP3935977.8 1989-10-28

Publications (1)

Publication Number Publication Date
CA2072104A1 true CA2072104A1 (en) 1991-04-29

Family

ID=6392444

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2072104 Abandoned CA2072104A1 (en) 1989-10-28 1990-10-24 Selective herbicides

Country Status (10)

Country Link
EP (1) EP0497806A1 (en)
JP (1) JPH05501251A (en)
AU (1) AU642920B2 (en)
CA (1) CA2072104A1 (en)
DE (1) DE3935977A1 (en)
HU (1) HUT60601A (en)
IE (1) IE903870A1 (en)
PL (1) PL287531A1 (en)
PT (1) PT95713A (en)
WO (1) WO1991006215A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6296864B1 (en) * 1996-11-01 2001-10-02 Sumitomo Chemical Company, Limited Pesticidal composition

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DK0514769T3 (en) * 1991-05-18 1997-02-10 Hoechst Schering Agrevo Gmbh
AU6576594A (en) * 1993-05-10 1994-12-12 Zeneca Limited Safening pyridyloxyphenoxy propionic acid herbicides
AUPN265895A0 (en) 1995-04-28 1995-05-25 Risk Management Resources Pty Ltd Control wheel assembly for trolleys
DE19913036A1 (en) * 1999-03-23 2000-09-28 Aventis Cropscience Gmbh Liquid preparations and surfactant / solvent systems
JP4543738B2 (en) * 2004-05-11 2010-09-15 住友化学株式会社 Agricultural emulsion

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3203779A1 (en) * 1982-02-04 1983-08-11 Hoechst Ag, 6230 Frankfurt HERBICIDAL AGENTS
GR78909B (en) * 1982-08-13 1984-10-02 Sipcam Spa
DE3525205A1 (en) * 1984-09-11 1986-03-20 Hoechst Ag, 6230 Frankfurt PLANT PROTECTIVE AGENTS BASED ON 1,2,4-TRIAZOLE DERIVATIVES AND NEW DERIVATIVES OF 1,2,4-TRIAZOLE
DD251276A5 (en) * 1985-06-04 1987-11-11 �������`�����@�������k�� STABILIZED LIQUID HERBICIDES COMPOSITIONS BASED ON M-BIS CARBANATES AND THEIR USE
ES2045184T3 (en) * 1987-10-02 1994-01-16 Ciba Geigy Ag DERIVATIVES OF THE ACID 1,5-DIFENIL-1,2,4-TRIAZOL-3-CARBOXILICO FOR THE PROTECTION OF CROP PLANTS AGAINST THE PHYTOTOXIC ACTION OF HERBICIDES.
DE3817192A1 (en) * 1988-05-20 1989-11-30 Hoechst Ag PLANT-PROTECTIVE AGENTS CONTAINING 1,2,4-TRIAZOLE DERIVATIVES AND NEW DERIVATIVES OF 1,2,4-TRIAZOLE

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6296864B1 (en) * 1996-11-01 2001-10-02 Sumitomo Chemical Company, Limited Pesticidal composition

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PT95713A (en) 1991-09-13
AU642920B2 (en) 1993-11-04
IE903870A1 (en) 1991-05-08
WO1991006215A1 (en) 1991-05-16
EP0497806A1 (en) 1992-08-12
PL287531A1 (en) 1991-10-21
DE3935977A1 (en) 1991-05-02
AU6549490A (en) 1991-05-31
JPH05501251A (en) 1993-03-11
HUT60601A (en) 1992-10-28

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