AP106A - Synergistic mixture - Google Patents

Synergistic mixture Download PDF

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Publication number
AP106A
AP106A APAP/P/1989/000138A AP8900138A AP106A AP 106 A AP106 A AP 106A AP 8900138 A AP8900138 A AP 8900138A AP 106 A AP106 A AP 106A
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ARIPO
Prior art keywords
chloroacetyl
dimethylaniline
methylaniline
ethyl
diethylaniline
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APAP/P/1989/000138A
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German (de)
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AP8900138A0 (en
Inventor
Wolfgang Paul Iwanzik
Willy Maurer
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Ciba Geigy Ag
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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
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof

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

Abstract

The invention relates to a herbicidal composition containing as active ingredient a chloroacetanilide of formula I wherein each of R1 and R2 , independently of the other, is hydrogen; halogen; C1-C4 alkyl; C1-C4alkoxy; C1-C4haloalkyl; or C1-C4 alkoxy-C1-C4-alkyl; Z is hydrogen; halogen; or C1-C4 alkyl; Y is C1-C6alkylene; R3 is C1-C4 alkoxy; C3-C4 alkenyloxy; cyano; C1-C4 alkoxycarbonyl; C1-C4-alkyl-CO-NH-; (R4)2N-CO-; benzoyl; halobenzoyl; 1,3-oxadiazol-2-yl, 1,3-dioxolan-2-yl, furan-2-yl, tetrahydrofuran-2-yl, 1,3,4-oxadiazol-2-yl, pyrazol-1-yl, 1,2,4-triazol-l-yl or 1,2,4-triazol-3-yl each of which is unsubstituted or substituted up to twice by the same or different C1-C4 alkyl; (C1-C4alkoxy) 2CH-; C1-C4,alkyl; ethynyl; or 4-methyl-5-methylthio-l ,2,4-triazol-3-yl; each R4, independently of the other, is hydrogen; C1-C4alkyl; C1-C4alkenyl; or C1-C4alkynyl, together with a synergistically effective amount of an N-chloroacetylcyclohexen-amine of formula II wherein R5 is C1-C6alkyl; or C3-C6alkenyl; and each of R6 , R7 , R8 and R9 , independently of the others, is hydrogen; or C1-C4,alkyl.

Description

The invention relates to a herbicidal composition containing as active ingredient a chloroacetanilide of formula I
R’-Y C-CHz-Cl
W* (I)
wherein each of R1 and R2, independently of the other, is hydrogen; halogen; Ci-C*alkyl; Ci~Ci,alkoxy; Ci-Ci,haloalkyl; or Ci-C<,alkoxy-Ci-Cualkyl; Z is hydrogen; halogen; or Ci~Ci,alkyl; Y is Ci-Cealkylene; RJ is Ci-Ci,alkoxy; Cj-Ci,alkenyloxy; cyano; Ci-Ci,alkoxycarbonyl; Ci-Ckalkyl-CO-NH-; (R*)2N-CO-; benzoyl; halobenzoyl; 1,3-oxadiazol-2-yl,
1,3-dioxolan-2-yl, furan-2-yl, tetrahydrofuran-2-yl, 1,3,4-oxadiazol2-yl, pyrazol-l-yl, 1,2,4-triazol-l-yl or 1,2,4-triazol-3-yl each·of which is unsubstituted or substituted up to twice by the same or different Cj-Cualkyl; (Cj-Ci,alkoxy)2CH-; Ci-Ci»alkyl; ethynyl; or 4-methyl-5-methylthio-l,2,4-triazol-3-yl; each R*, independently of the other, is hydrogen; Ci-Cualkyl; Ci-Ci,alkenyl; or Ci-Ci,alkynyl, together with a synergistically effective amount of an N-chloroacetylcyclohexenamine of formula II
AP 0 0 0 1 0 6 (II) wherein R5 is Ci-C&alkyl; or Cj-Cealkenyl; and each of R6, R7, R* and R5 , independently of the others, is hydrogen; or Cj-Cualkyl.
BAD ORIGINAL
5-17192/=
Synergistic mixture
The invention relates to a synergistic composition containing a herbicidal combination of active ingredients. The composition according to the invention is especially suitable for the selective control of weeds in crops of useful plants.
The invention relates also to a method of controlling weeds in crops of useful plants.
A large number of herbicidally active compounds from the chloroacetanilide class are already known. A compilation of that class of compounds can be found in R. Wegler, Chemie der Pflanzenschutz- und Schadlingsbekampfungsmittel, Springer Verlag, Berlin, Heidelberg, New York, Vol. 2 (1970) page 311 ff., Vol. 5 (1977) page 244 ff. and Vol. 8 (1982) page 90 ff. and page 310 ff. These compounds are not always satisfactory as regards their strength of action, duration of action and range of application in respect of the crop weeds to be controlled.
A further class of herbicidally active acetylamines are the N-chioroacetylcyclohexenamines which have been disclosed in US Patent Specification US 4 351 667, EP-A-13 429 and EP-A-0 113 030. These compounds too are selective herbicides that are not always satisfactory as regards their strength of action, duration of action and their range of application in respect of the crop weeds to be controlled. In particular, these N-chloroacetylcyclohexenamines are not satisfactory as regards their ^Long-term action.
BAD ORIGINAL
It has surprisingly now been found that a quantitatively variable combination of compounds from the chloroacetanilide class with compounds from the N-chloroacetylcyclohexenamine class exhibits a synergistic action which is advantageously suitable for controlling weeds in crops of useful plants.
This synergistic combination is suitable for controlling the most important weeds without at the same time damaging the cultivated plant.
In addition, in the case of some crop weeds, an enhancement of the long-term action is observed.
The invention relates to a novel herbicidal composition for selective weed control, containing as active ingredient a chloroacetanilide of formula I
R’-Y C-CHj-Cl (I)
II wherein each of R1 and R2, independently of the other, is hydrogen; halogen; Ci-Ci,alkyl; Ci~Ci»alkoxy; Ci-Cuhaloalkyl; or Ci~Ci,alkoxy-Ci-C<,alkyl; 2 is hydrogen; halogen; or Cj-Cualkyl; Y is Ci-C6alkylene; R3 is Ci-Ci,alkoxy; Cj-Cualkenyloxy; cyano; Ci~Ci,alkoxycarbonyl; Ci-Ci»alkyl-CO-NH-; (R*)zN-CO-; benzoyl; halobenzoyl; 1,3-oxadiazol-2-yl,
1,3-dioxolan-2-yl, furan-2-yl, tetrahydrofuran-2-yl, 1,3,4-oxadiazol2-yl, pyrazol-1-yl, 1,2,4-triazol-l-yl or 1,2,4-triazol-3-yl each of which is unsubstituted or substituted up to twice by the same or different Ci-Ci,alkyl; (Ci-Ci,alkoxy) 2CH-; Ci-Cualkyl; ethynyl; or 4-methyl-5-methylthio-l,2,4-triazol-3-yl; each R* , independently of the other, is hydrogen; Ci-Ci,alkyl; Cj —Cualkenyl; or Ci-Ci,alkynyl, together with a synergistically effective amount of an N-chloroacetylcyclohexenamine of formula II
AP 0 0 0 1 0 6 bad original
R6
R7
CHz-Cl (II) wherein Rs is Ci-Cealkyl; or Cj-Cealkenyl; and each of R6, R7, R* and R9, independently of the others, is hydrogen; or Ci-Ci,alkyl.
In the definitions used in this description, the generic terms given, and substituents obtainable by combining individual sub-meanings, include, for example, the following specific individual substituents, but this list does not constitute a limitation of the invention:
Alkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl, isobutyl and tert.-butyl; preferably methyl, ethyl and isopropyl.
Halogen: fluorine, chlorine, bromine and iodine; preferably fluorine, chlorine and bromine; especially preferred fluorine and chlorine.
Haloalkyl: fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl and 2,2,2-trichloroethyl.
Alkoxy: methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy and tert.-butoxy.
Alkoxycarbonyl: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and n-butoxycarbonyl; preferably methoxycarbonyl and ethoxycarbonyl.
Halobenzoyl: chlorobenzoyl, especially 4-chlorobenzoyl.
i
Ci~C6alkylene: methylene, 1,2-ethylene, 1,1-ethylene, 1-methyl-1,2ethylene, 1-ethyl-l,2-ethylene, 2-methyl-l,2-ethylene, l-(l-methylethyl)-l,2-ethylene, 2-(l-methylethyl)-l,2-ethylene, 1,2-dimethy1-1,2ethylene.
BAD ORIGINAL
C3~Cualkenyloxy: in these radicals the double bond is preferably bonded in allyl manner to the oxygen atom, that is to say allyloxy and but-2enyloxy.
Preferred compounds of formula I are those wherein R1 is hydrogen; chlorine; Ci~Ci,alkyl; methoxy; or trifluoromethyl; R* is hydrogen; methyl; or ethyl; 2 is hydrogen; or methyl; Y is methylene; 1,2-ethylene; 1-methy1-1,2-ethylene; 2-methyl-l,2-ethylene; 1-ethyl-l,2-ethylene;
1-(1-methylethyl)-l,2-ethylene; or 1,2-dimethyl-l,2-ethylene; R3 is Ci-Cualkoxy; allyloxy; cyano; Ci-Cjalkoxycarbonyl; acetylamino; N-allylcarbamoyl; Ν,Ν-dimethylcarbamoyl; benzoyl; 4-chlorobenzoyl; 1,3-oxadiazol-2-yl; 1,3-dioxolan-2-yl; furan-2-yl; tetrahydrofuran-2-yl; 1,3,4-oxadiazol-2-yl; pyrazol-l-yl; 3,5-dimethylpyrazol-l-yl; 1,2,4-triazol-l-yl; 5-methyl-l,3,4-oxadiazol-2-yl; 4-methy1-5-methy1thio-1,2,4-triazol-3-yl; isopropyl; ethynyl; or (ethoxy)2CH.
As individual representatives of the chloroacetanilides of formula I, the following should be given prominence:
N-ethoxymethyl-N-chloroacetyl-2-ethyl-6-methylaniline,
N-chloroacetyl-N-methoxymethyl-2,6-diethylaniline (Alachlor),
N-chloroacetyl-N-(2-methoxyethyl)-2,6-dimethylaniline,
N-(2-allyloxyethyl)-N-chloroacetyl-2,6-dimethylaniline,
N-chloroacetyl-N-(2-n-propoxyethyl)-2,6-dimethylaniline,
N-chloroacetyl-N-(2-isopropoxyethyl)-2,6-dimethylaniline,
N-chloroacetyl-N-(2-methoxyethyl)-2-ethy1-6-methylaniline,
N-chloroacetyl-N-(methoxyethyl)-2,6-diethylaniline,
N-(2-ethoxyethy1)-N-chloroacety1-2-ethy1-6-methylaniline,
N-chloroacetyl-N-(2-methoxy-1-methylethy1)-2-methylanilire,
N-chloroacetyl-N-(2-methoxy-1-methylethy1)-2,6-dimethylar iline,
N-chloroacetyl-N-(2-methoxy-l-methylethyl)-2,6-diethylaniline,
N-chloroacetyl-N-(2-methoxy-1-methylethyl)-2-ethy1-6-methylaniline (Metolachlor),
N-(2-ethoxyethyl)-N-chloroacety1-2,6-diethylaniline, ,
N-chloroacetyl-N-(2-n-propoxyethyl)-2-ethyl-6-methylaniline, N-chloroacetyl-N-(2-n-propoxyethyl)-2,6-diethylaniline,
BAD ORIGINAL
N-chloroacety1-N-(2-isopropoxyethyl)-2-ethy1-6-methylaniline, N-ethoxycarbonylmethyl-N-chloroacety1-2,6-dimethylaniline, N-ethoxycarbonylmethyl-N-chloroacetyl-2,6-diethylaniline , N-chloroacetyl-N-methoxycarbonylmethyl-2,6-dimethylaniline,
N-chloroacety1-N-(2,2-diethoxyethy1)-2,6-dimethylaniline, N-chloroacetyl-N-(2-methoxy-l-methylethyl)-2,3-dimethylaniline ,
N-(2-ethoxyethyl)-N-chloroacetyl-2-methylaniline,
N-chloroacety1-N-(2-methoxyethy1)-2-methylaniline,
N-chloroacety1-N-(2-methoxy-2-methylethy1)-2,6-dimethylaniline ,
N-( 2-ethoxy-2-methylethyl)-N-chloroacetyl-2-ethy1-6-methylaniline, N-chloroacetyl-N-(1-ethy1-2-methoxyethy1)-2,6-dimethylaniline, N-chloroacetyl-N-(2-methoxyethy1)-2-methoxy-6-methylaniline, N-n-butoxymethyl-N-chloroacetyl-2-tert.-butylaniline ,
N-( 2-ethoxyethy1-1-methylethyl)-N-chloroacety1-2,6-dimethylaniline, N-chloroacety1-N-(2-methoxyethyl)-2-chloro-6-methylaniline,
N-(2-ethoxyethyl)-N-chloroacetyl-2-chloro-6-methylaniline,
N-(2-ethoxyethyl)-N-chloroacety1-2,3,6-1rimethylaniline,
N-chloroacety1-N-(2-methoxyethy1)-2,3,6-trimethylaniline, N-chloroacetyl-N-cyanomethyl-2,6-dimethylaniline,
N-but-3-yn-l-yl-N-chloroacetylaniline,
N-chloroacetyl-N-propargyl-2-ethy1-6-methylaniline,
N-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-dimethylaniline, N-chloroacety1-N-(1,3-dioxolan-2-ylmethyl)-2-ethy1-6-methylaniline, N-chloroacetyl-N-( 1,3-dioxan-2-ylmethyl)-2-ethyl-6-methylaniline, N-chloroacety1-N-(2-furanyImethy1)-2,6-dimethylaniline,
N-chloroacety1-N-(2-furanyImethyl)-2-ethyl-6-methylaniline,
N-chloroacetyl-N-(2-tetrahydrofuranyImethy1)-2,6-dimethylaniline, N-chloroacety1-N-(N-propargylcarbamoyImethyl)-2,6-dimethylaniline, N-chloroacetyl-N-(N,N-dimethylcarbamoyImethyl)-2,6-dimethylaniline, N-(n-butoxymethyl)-N-chloroacety1-2,6-diethylaniline ,
N-(2-n-butoxyethyl)-N-chloroacety1-2,6-diethylaniline,
N-chloroacety1-N-(2-methoxy-1,2-dimethylethyl)-2,6-dimethylaniline, N-chloroacety1-N-isopropyl-2,3-dimethylaniline, N-chloroacetyl-N-isopropyl-2-chloroaniline,
N-chloroacetyl-N-(1H-pyrazol-1-yImethy1)-2,6-dimethylaniline (Metazachlor),
N-chloroacetyl-N-(1H-pyrazol-1-ylmethyl)-2-ethy1-6-methylaniline, bad original
/···
-6N-chloroacetyl-N-(1 Η—1,2,4-triazol-l-ylmethyl)-2,6-dimethylaniline ,
N-chloroacetyl-N-(1Η—1,2,4-triazol-l-ylmethyl)-2,6-diethylaniline .
N-benzoylmethyl-N-chloroacetyl-2,6-dimethylaniline,
N-benzoylmethyl-N-chloroacetyl-2-ethyl-6-methylaniline,
N-chloroacetyl-N-(5-methyl-l,3,4-cxadiazol-2-yl)-2,6-diethylaniline, N-chloroacetyl-N-(5-methyl-l,3,4-oxadiazol-2-yl)-2-ethyl-6-methylaniline, N-chloroacetyl-N-(5-methyl-l,3,4-oxadiazol-2-yl)-2-tert.-butylaniline, N-chloroacetyl-N-(4-chlorobenzoylmethyl)-2,6-dimethylaniline,
N-chloroacetyl-N-(l-methyl-5-methylthio-l,3,4-triazol-2-ylmethyl)-2,6diethylaniline,
N-chloroacetyl-N-ethoxymethyl-6-methyl-2-trifluoromethylaniline (Harmony) and
N-chloroacetyl-N-acetamidomethyl-2,6-diethylaniline (Amidochlor).
Especially preferred are
N-chloroacetyl-N-methoxymethyl-2,6-diethylaniline (Alachlor),
N-chloroacetyl-N-(2-methoxy-l-methylethyl)-2-ethyl-6-methylaniline (Metolachlor) and
N-chloroacetyl-N-(lH-pyrazol-l-ylmethyl)-2,6-dimethylaniline (Metazachlor).
Preferred N-chloroacetylcyclohexenamines are the compounds of formula II wherein Rs is Ci-Ci,alkyl or Cj-Ci,alkenyl, and each of R6 , R7 , Re and R’ , independently of the others, is hydrogen or Ci-Cialkyl.
Prominence is to be given to the compounds of formula II wherein R5 is Ci-Cualkyl or Cj-Ci,alkenyl, and each of R6 , R7 , R* and R3 , independently of the others, is hydrogen or methyl.
Especially preferred are
Ή-isopropyl-N-chloroacetyIcyclohex-1-enamine,
N-isopropyl-N-chloroacetyl-3(5)-methylcyclohex-l-enamine,
N-isopropyl-N-chloroacetyl-3,5,5(3)-trimethylcyclohex-l-enamine (Trimexachlor),
N-isopropyl-N-chloroacetyl-3,3,5,5-tetramethylcyclohex-l-enamine and N-allyl-N-chloroacetyl-3,3,5,5-tetramethylcyclohex-l-enamine, bad ORIGINAL
AP 0 0 0 1 0 6 but especially
N-isopropyl-N-chloroacetyl-3,5, 5( 3)-trimethylcyclohex-l-enamine (Trimexachlor).
Within the scope of the present invention, cultivated plants are·to be understood as being all plants that yield any form of produce, such as seeds, roots, stalks, tubers, leaves, blossom, and also extracts, such as oils, sugars, starch, protein, etc., and are cultivated for that purpose. These plants include, for example, all species of cereal, such as wheat, rye, barley and oats, and, in addition, especially rice, sorghum, maize, cotton, sugar beet, groundnuts, sugar cane, soya, beans, sunflowers and peas.
The active ingredient combination according to the invention is especially suitable for controlling weeds in maize, rice, sorghum, soya, sugar beet, cotton, sunflower and groundnut crops.
The combinations of the haloacetanilides of formula I mentioned as individual compounds and the N-chloroacetylcyclohexenamines of formula II mentioned as individual compounds are especially suitable for the above-mentioned target crops.
The following combinations are to be given special prominence:
a) N-chloroacetyl-N-methoxymethyl-2,6-diethylaniline and N-isopropyl-Nchloroacetyl-3, 5,5(3)-trimethylcyclohex-l-enamine,
b) N-chloroacetyl-N-(2-methoxy-1-methylethy1)-2-ethy1-6-methylaniline and N-isopropyl-N-chloroacetyl-2,5,5(3)-trimethylcyclohex-l-enamine and
c) N-chloroacetyl-N-(ΙΗ-pyrazol-1-ylmethy1)-2,6-dimethylaniline and N-isopropyl-N-chloroacetyl-3,5,5(3)-trimethylcyclohex-l-enamine.
The active ingredient combinations according to the invention can be used both pre- and post-emergence. In addition, the seeds of the useful plant; can be treated with a herbicidally effective amount of the active
BAD ORIGINAL ingredient combination according to the invention (seed dressing). The compound combination according to the invention is thus applied when the seeds of the useful plants are sown.
It is extremely surprising that the combination of the compound of formula I with a compound of formula II not only brings about an additive increase in the spectrum of action against the normal weeds associated with the cultivated plant in question, which would be expected in principle, but also achieves a synergistic effect which broadens in two respects the range of action of the active substances that are combined with one another.
Firstly, the rates of application of the individual compounds I and II are significantly reduced while the high level of action is maintained. Secondly, the combined mixture still achieves a high degree of weed control even in cases where the two compounds individually were entirely ineffective when used at too low a rate of application. The result of this is a considerable broadening of the weed spectrum and an additional increase in the safety margin in respect of the particular cultivated plant, as is necessary and desirable in case of inadvertent overdosage of the active ingredient. It has also been found that, in the case of some weeds, the long-term-action of the mixture exceeds that of the individual components.
The optimum mixing ratio of the individual active ingredient components for the desired use can be determined by biological tests. The ratios of the individual active ingredient components can vary in accordance with the type of weed to be controlled and in dependence on the particular form of application.
Although the mixing ratio can therefore be freely selected within wide limits, mixtures of compounds of formula I with those of formula II in which the ratio by weight of the individual components I:II varies from 5:1 to 1:5 are preferred.
AP 0 0 0 1 0 6 a
bad ORIGINAL
J* *
- 9 The range from 2:1 to 1:2 is especially preferred. Special prominence is to be given to mixtures of equivalent or almost equivalent (such as, for example, in the range of from 1.5:1 to 1:1.5) parts by weight of the two compound components.
The active ingredient combinations according to the invention exhibit excellent action against weeds, without having any appreciable effect on the useful plant crop, at a rate of application of from 0.1 to 5.0 kg, preferably from 0.25 to 4.0 kg, of active substance per hectare.
The formulations, i.e. the compositions, preparations or mixtures containing the active ingredient mixture according to the invention and, where appropriate, a solid or liquid adjuvant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredients with extenders, e.g. solvents or other liquids in which the active ingredients can be dispersed, solid carriers and, where appropriate, surface-active compounds (surfactants).
Suitable solvents or dispersants are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monoroethyl or monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, as well as vegetable oils or epoxidised vegetable oils, such as epoxidised coconut oil or soybean oil; or water.
The solid carriers used e.g. for dusts and dispersible powders, are normally natural mineral fillers such as calcite, talcum, kaolin, ^lontmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are, for example, calcite or sand. In
BAD ORIGINAL addition, a great number of pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverised plant residues, such as cork powder and sawdust.
Particularly advantageous application-promoting adjuvants which are able to reduce substantially the rate of application are also natural (animal or vegetable) or synthetic phospholipids of the series of the cephalins and lecithins, e.g. phosphatidylethanolamine, phosphatidylserine, phosphatidylcholine, sphingomyelin, phosphatidylinositol, phosphatidylglycerol, lysolecithin, plasmalogens or cardiolipin, which can be obtained e.g. from animal or vegetable cells, especially the brain, heart, lungs, liver, egg yolks or soybeans. Commercial mixtures that may be used are e.g. phosphatidylcholine mixtures. Synthetic phospholipids are e.g. dioctanoylphosphatidylcholine and dipalmitoylphosphatidylcholine.
Suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. The term surfactants will also be understood as comprising mixtures of surfactants.
Both so-called water-soluble soaps and also water-soluble synthetic surface-active compounds are suitable anionic surfactants.
Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C10-C22), e.g. the sodium or potassium salts of oleic or stearic acid or of natural fatty acid mixtures which can be obtained e.g. from coconut oil or tallow oil. Mention may also be made of fatty acid methyltaurin salts.
More frequently, however, so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
APO0 0 106 bad original
The fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and contain a Ce~C22alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfated and sulfonated fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a condensate of naphthalenesulfonic acid and formaldehyde.
Also suitable are corresponding phosphates, e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 moles of ethylene oxide.
Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.
Further suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
Representative examples of non-ionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
BAD ORIGINAL d
Fatty acid esters of polyoxyethylene sorbitan, e.g. polyoxyethylene sorbitan trioleate, are also suitable non-ionic surfactants.
Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one Ce-C22~alkyl radical and·, as further substituents, unsubstituted or halogenated lower alkyl, or benzyl or hydroxy-lower alkyl radicals. The salts are.preferably in the form of halides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.
The surfactants customarily employed in the art of formulation are described, inter alia, in the following publications:
1985 International Me Cutcheon's Emulsifiers & Detergents,
Glen Rock NJ USA, 1985,
H. Stache, Tensid-Taschenbuch, 2nd Edition, C. Hanser Verlag, Munich, Vienna 1981,
M. and J. Ash Encyclopedia of Surfactants, Vol. I-III, Chemical Publishing Co., New York, 1980-1981.
The agrochemical compositions usually contain 0.1 to 95 %, preferably 0.1 to 80 %, of mixture of compounds of formulae I and II, 1 to 99.9 % of a solid or liquid adjuvant, and 0 to 25 %, preferably 0.1 to 25 %, of a surfactant.
Preferred formulations have especially the following compositions: (throughout, percentages are by weight)
Emulsifiable concentrates
AP 0 0 0 1 0 6
active ingredient mixture: 1 to 20 %, preferably 5 to 10 %
surface-active agent: 5 to 30 %, preferably 10 to 20 %
liquid carrier: 50 to 94 preferably 70 to 85 %
bad ORIGINAL
Dusts active ingredient mixture solid carrier:
0.1 to 10 %, preferably 0.1 to 1 % 99.9 to 90 X, preferably 99.9 to 99 %
Suspension concentrates
active ingredient mixture: 5 to 75 X, preferably 10 to 50 %
water: 94 to 25 X, preferably 88 to 30 X
surface-active agent: 1 to 40 %, preferably 2 to 30 X
Wettable powders active ingredient mixture surface-active agent: solid carrier:
to 90 X, 5 to 20 X, to 95 %, preferably preferably preferably to 80 X 1 to 15 X 15 to 90 %
Granulates active ingredient mixture solid carrier:
0.5 to 30 X, 99.5 to 70 X, preferably 3 to preferably 97, to % 85 %
Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations. The forms of application can be diluted to concentrations as low as 0.001 % active ingredient.
In addition to the mentioned preferred formulations in the form of emulsifiable concentrates, dusts, suspension concentrates, wettable powders and granulates, the combinations according to the invention can also be formulated as microcapsules according to EP-A-0 281 521 published on 07.09.1988.
Other biocidal active ingredients or compositions can be m.'.xed with the described compositions according to the invention. For exanple, the novel ^compositions may contain, in addition to the mentioned compounds of the general formula I and formula II, for example insecticides, fungicides, bactericides, fungistatics, bacteriostatics or nematicides in order to broaden the spectrum of action.
BAD ORIGINAL
The compositions according to the invention can generally be formulated, in detail, in accordance with the following Examples:
Formulation Examples
Example Fl:
Formulation Examples for synergistic mixtures of compounds of formulae I and II (throughout, percentages are by weight)
a) Wettable powders a) b) c) d)
compound of formula I 10 % 20 % 15 % 30 %
compound of formula II 10 % 40 % 5 % 30 %
sodium lignosulfonate 5 % 5 % 5 % 5 %
sodium lauryl sulfate 3 % - 3 % -
sodium diisobutylnaphtha lene sulfonate - 6 % - 6 %
octylphenolpolyethylene glycol ether (7-8 moles of ethylene oxide) 2 % 2 % -
highly dispersed silicic acid 5 % 27 % 5 % 27 %
kaolin 67 % - 67 % -
The active ingredient mixture is thoroughly mixed with the adjuvants and
the mixture is thoroughly ground in a suitable mill, affording wettable
powders which can be diluted with water to give suspensions of the
desired concentration.
b) Emulsifiable concentrate a) b) c) d) e)
compound of formula I 5 % 15 % 12 % 25 % 30 %
compound of formula II 5 %. 10 % 13 % 25 % 30 %
octylphenolpolyethylene glycol ether (4-5 moles of .ethylene oxide) 3 % 3 % 3 % 3 % 3 %
calcium dodecylbenzene sulfonate 3 % 3 % 2 % 5 % 5 X
castor oil polyglycol ether (36 moles of ethylene oxide) 4 % 4 % 4 % 4 % 4 %
cyclohexanone 30 % 30 % 31 % 15 % 10 %
xylene mixture 50 % 35 % 35 % 13 % 8 %
AP 0 0 0 1 0 6 bad original »
- 15 Emulsions of any required concentrates by dilution
c) Dusts compound of formula I compound of formula talcum kaolin
Ready-for-use dusts are obtained by carrier and grinding the mixture in concentration can with water.
a) %
II 3 % %
d) Extruder granulate a) compound of formula I 5 % compound of formula II 5 % sodium lignosulfonate 2 % carboxymethylcellulose 1 % kaolin 87 % be obtained from these
b) c) d) % 2 % 8 % % 4 % 4 % %
% - 88 % mixing the compound mixture with the a suitable mill.
b) c) % 10 % % 10 % % 2 % % 1 % % 77 %
The active ingredient mixture is mixed and ground with the adjuvants, and the mixture is subsequently moistened with water. The mixture is extruded and then dried in a stream of air.
e) Coated granulate a) b) compound of formula I 1.5 % 3 % compound of formula II 1.5 % 5 % polyethylene glycol (mol. wt. 200) 3 % 3 % kaolin 94 % 89 %
The finely ground active ingrediert mixture is uniformly applied, in a .mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granulates are obtained in this manner.
BAD ORIGINAL
f) Suspension concentrate a) b) c)
compound of formula I 20 % 20 % 40 %
compound of formula II 20 % 40 % 20 %
ethylene glycol 10 % 10 % 10 %
nonylphenolpolyethylene glycol
ether (15 moles of ethylene oxide) 6 % 6 % 6 %
sodium lignosulfonate 10 % 10 % 10 %
carboxymethyIcellulose 1 % 1 % 1 %
37 % aqueous formaldehyde so ilution 0. .2 % 0. .2 % 0. ,2
silicone oil in the form of a 75 %
aqueous emulsion 0. .8 % 0. .8 % 0. ,8
water 32 % 12 % 12 %
The finely ground active ingredient mixture is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.
A synergistic effect is always present in the case of herbicides when the herbicidal action of the combination of compounds I and II is greater than the total action of the active ingredients applied individually.
The expected herbicidal action Ae for a given combination of two herbicides can be calculated as follows (cf. COLBY, S.R., Calculating synergistic and antagonistic response of herbicide combinations,
Weeds 15, pages 20-22, 1967):
Ae
Y * Y x (100-X) X 100
AP 0 0 0 1 0 6 in which:
X = percentage inhibition of growth in the case of treatment with a herbicide I at a rate of application of p kg per hectare in comparison With the untreated control (= 0 %)
Y = percentage inhibition of growth in the case of treatment with a herbicide II at a rate of application of q kg per hectare in comparison ' with the untreated control bad OFUG'NAL
Ae expected herbicidal action (percentage inhibition of growth in comparison with the untreated control) after treatment with herbicide mixture I and II at a rate of application of p + q kg of active ingredient per hectare.
If the action actually observed is greater than the expected value Ae then synergism has been achieved.
The synergistic effect of the combinations of compounds I and II is demonstrated in the following Examples.
Biological Examples:
Example Bl: Pre-emergence test
Methodology
The plant seeds are sown in plastics pots containing 0.5 litre of soil, in a greenhouse. The herbicides are applied individually or in the form of a tank mixture of 2 products after sowing but before the emergence of the plants.
The biological activity is evaluated as percentage weed control in comparison with untreated control plants 21 days after application. Colby's formula is used to establish whether the mixtures achieve a synergistic increase in action in comparison with the individual · products.
The results show that in some cases the mixtures bring about a very marked synergistic increase in action.
BAD ORIGINAL
Table la: Synergistic action of Trimexachlor in a tank mixture with Metolachlor
treatment Trimexachlor 125 g Al/ha
+ Metolachlor 125 g Al/ha
plant species Ae A
Sorghum halepense 87 99
Alopecurus myosuroides 85 95
Amaranthus retroflexus 73 95
Ae = expected value according to Colby A - value measured
Table lb: Action of the individual components
Trimexachlor 125 g Al/ha Metolachlor 125 g Al/ha
Sorghum halepense 85 10
Alopecurus myosuroides 85 0
Amaranthus retroflexus 10 70
AP 0 0 0 1 0 6
Table 2a: Synergistic action of Trimexachlor in a tank mixture with Alachlor
treatment Trimexachlor 125 g Al/ha
+ Alachlor 125 g Al/ha
plant species Ae A
Sorghum halepense 88 100
Alopecurus myosuroides 87 97
Cyperus esculentus 64 80
Ae = expected value according to Colby A = value measured
BAD ORIGINAL
- 19 Table 2b: Action of the individual components
Trimexachlor 125 g Al/ha Alachlor 125 g Al/ha
Sorghum halepense 85 20
Alopecurus myosuroides 85 10
Cyperus esculentus 40 40
Table 3a: Synergistic action of Trimexachlor in a tank mixture with Metazachlor
treatment Trimexachlor + Metazachlor 62,5 g Al/ha 62,5 g Al/ha
plant species Ae A
Sorghum halepense 55 95
Solanum nigrum 95 100
Amaranthus retroflexus 90 100
Ae = expected value according to Colby A = value measured.
Table 3b: Action of the individual components
Trimexachlor 62,5 g Al/ha Metazachlor 62,5 g Al/ha
Sorghum halepense 50 10
Solanum nigrum 0 95
Amaranthus retroflexus 0- 90
“Example B2: Pre-emergence test, long-term action against Echinochloa Methodology
After a single application of the active ingredient or the active ingredient mixture to active soil, the pots are left at room temperature and Echinochloa crus galli is sown immediately after application and thereafter at weekly intervals.
The action on the plants from each sowing is evaluated 2 weeks after that sowing as % activity in comparison with the untreated control.
The results of this test are compiled in Table 4.
Table 4
weeks after application
g Al/ha 0 1 2 3 4 5 6 7
Trimexachlor 250 100* 40 0
500 100 95 10 0
Metolachlor 250 100 98 95 90 90 0
500 100 100 98 98 95 70 20 0
Trimexachlor 125
+ 100 100 95 95 95 80 70 0
Metolachlor 125
Trimexachlor 250
+ 100 100 100 98 98 95 95 40
Metolachlor 250
* percentage activity against Echinochloa

Claims (15)

1. A herbicidal composition containing as active ingredient a chloroacetanilide of formula I c-ch2-Cl «kA/1
R3-Y, >2 (I) wherein each of R1 and R2, independently of the other, is hydrogen; halogen; Ci-Cualkyl; Ci-Cualkoxy; Ci-Cuhaloalkyl; or Cj-Cualkoxy-Ci-Ci,alkyl; Z is hydrogen; halogen; or Ci~Ci,alkyl; Y is Cl-C6alkylene; R3 is Ci-Ci,alkoxy; C3-C4alkenyloxy; cyano; Ci-Cualkoxycarbonyl; Cx-Ci,alkyl-CO-NH-; (Rl,)zN-CO-; benzoyl; halobenzoyl; 1,3-oxadiazol-2-yl,
1,3-dioxolan-2-yl, furan-2-yl, tetrahydrofuran-2-yl, 1,3,4-oxadiazol2-yl, pyrazol-l-yl, 1,2,4-triazol-l-yl or 1,2,4-triazol-3-yl each of which is unsubstituted or substituted up to twice by the same or different Ci-Cualkyl; (Ci-Cualkoxy)2CH-; Ci-Cualkyl; ethynyl; or 4-methyl-5-methylthio-l,2,4-triazol-3-yl; each R*, independently of the other, is hydrogen; Ci-Ci,alkyl; Ci~Ci,alkenyl; or Ci-Ci,alkynyl, together with a synergistically effective amount of an N-chloroacetylcyclohexenamine of formula II
X Χ·Ζ V (II) wherein R5 is Cj-Cealkyl; or Cj-Csalkenyl; ard each of R6 , R7 , R8 and R3 , independently of the others, is hydrogen; or Ci-Ci,alkyl.
2. A composition according to claim 1, containing a compound of formula I wherein Rl is hydrogen; chlorine; Ci-Cualkyl; methoxy; or trifluoromethyl; R2 is hydrogen; methyl; or ethyl; Z is hydrogen; or methyl; Y is «
methylene; 1,2-ethylene; 1-methyl-l,2-ethylene; 2-methyl-l,2-ethylene;
1-ethyl-1,2-ethylene; 1-(l-methylethyl)-l,2-ethylene; or 1,2-dimethyl*
- 22 1,2-ethylene; RJ is Ci-Cualkoxy; allyloxy; cyano; Ci-Cjalkoxycarbonyl; acetylamino; N-allylcarbamoyl; N,N-dimethylcarbamoyl; benzoyl; 4-chlorobenzoyl; 1,3-oxadiazol-2-yl; 1,3-dioxolan-2-yl; furan-2-yl; tetrahydrofuran-2-yl; 1,3,4-oxadiazol-2-yl; pyrazol-1-yl; 3,5-dimethylpyrazol-l-yl;
1,2,4-triazol-l-yl; 5-methyl-l,3,4-oxadiazol-2-yl; 4-methyl-5-methylthio-1,2,4-triazol-3-yl; isopropyl; ethynyl; or (ethoxy)2CH.
3. A composition according to claim 1 or claim 2, containing
N-ethoxymethyl-N-chloroacetyl-2-ethyl-6-methylaniline,
N-chloroacetyl-N-methoxymethyl-2,6-diethylaniline (Alachlor),
N-chloroacetyl-N-(2-methoxyethy1)-2,6-dimethylaniline,
N-( 2-allyloxyethyl)-N-chloroacetyl-2,6-dimethylaniline,
N-chloroacetyl-N-(2-n-propoxyethyl)-2,6-dimethylaniline,
N-chloroacetyl-N-(2-isopropoxyethy1)-2,6-dimethylaniline,
N-chloroacetyl-N-(2~methoxyethyl)-2-ethyl-6-methylaniline,
N-chloroacetyl-N-(methoxyethyl)-2,6-diethylaniline,
N-(2-ethoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniiine,
N-chloroacetyl-N-(2-methoxy-l-methylethyl)-2-methylaniline,
N-chloroacetyl-N-(2-methoxy-l-methylethyl)-2,6-dimethylaniline,
N-chloroacetyl-N-(2-methoxy-l-methylethyl)-2,6-diethylaniline,
N-chloroacetyl-N-(2-methoxy-l-methylethyl)-2-ethyl-6-methylaniline (Metolachlor),
N-(2-ethoxyethyl)-N-chloroacetyl-2,6-diethylaniline,
N-chloroacetyl-N-(2-n-propoxyethyl)-2-ethyl-6-methylaniline,
N-chloroacetyl-N-(2-n-propoxyethyl)-2,6-diethylaniline,
N-chloroacetyl-N-(2-isopropoxyethyl)-2-ethyl-6-methylaniline,
N-ethoxycarbonylmethyl-N-chloroacetyl-2,6-dimethylaniline,
N-ethoxycarbonylmethyl-N-chloroacetyl-2,6-diethylaniline,
N-chloroacetyl-N-methoxycarbonylmethyl-2,6-dimethylaniline,
N-chloroacetyl-N-(2,2-diethoxyethy1)-2,6-dimethylaniline,
N-chloroacetyl-N-(2-methoxy-l-methylethy1)-2,3-dimethylaniline, ,N-(2-ethoxyethyl)-N-chloroacetyl-2-methylaniline,
N-chloroacetyl-N-(2-methoxyethyl)-2-methylaniline,
N-chloroacetyl-N-(2-methoxy-2-methylethyl)-2,6-dimethylaniline,
N-(2-ethoxy-2-methylethyl)-N-chloroacetyl-2-ethy1-6-methylaniline, N-chloroacetyl-N-(l-ethyl-2-methoxyethyl)-2,6-dimethylaniline, N-chloroacetyl-N-(2-methoxyethyl)-2-methoxy-6-methylaniline,
BAD ORIGINAL
AP 0 0 0 1 0 6
23 N-n-butoxymethy1-N-chloroacety1-2-tert.-butylaniline,
N-(2-ethoxyethy1-1-methylethy1)-N-chloroacetyl-2,6-dimethylaniline, N-chloroacetyl-N-(2-methoxyethyl)-2-chloro-6-methylaniline,
N-( 2-ethoxyethyl)-N-chloroacetyl-2-chloro-6-methylaniline,
N-( 2-ethoxyethyl)-N-chloroacetyl-2,3,6-trimethylaniline,
N-chloroacetyl-N-(2-methoxyethyl)-2,3,6-trimethylaniline, N-chloroacetyl-N-cyanomethyl-2,6-dimethylaniline,
N-but-3-yn-l-yl-N-chloroacetylaniline,
N-chloroacetyl-N-propargyl-2-ethyl-6-methylaniline,
N-chloroacetyl-N-( 1,3-dioxolan-2-yImethyl)-2,6-dimethylaniline,
N-chloroacetyl-N-( 1,3-dioxolan-2-ylmethyl)-2-ethyl-6-methylaniline, N-chloroacetyl-N-( 1,3-dioxan-2-ylmethyl)-2-ethyl-6-methylaniline, N-chloroacetyl-N-(2-furanylmethyl)-2,6-dimethylaniline,
N-chloroacetyl-N-(2-f uranylmethyl)-2-ethyl-6-methylaniline,
N-chloroacetyl-N-(2-tetrahydrofuranylmethyl)-2,6-dimethylaniline, N-chloroacetyl-N-(N-propargylcarbamoy Imethyl)-2,6-dimethylaniline, N-chloroacetyl-N-(N, N-dimethylcarbamoy Imethyl) -2,6-dimethylaniline, N-(n-butoxymethyl)-N-chloroacetyl-2,6-diethylaniline,
N-( 2-n-butoxyethyl)-N-chloroacetyl-2,6-diethylaniline,
N-chloroacetyl-N-(2-methoxy-l,2-dimethylethyl)-2,6-dimethylaniline, N-chloroacetyl-N-isopropyl-2,3-dimethylaniline,
N-chloroacetyl-N-isopropy1-2-chloroaniline,
N-chloroacetyl-N-( IH-pyrazol-l-yImethyl)-2,6-dimethylaniline (Metazachlor),
N-chloroacetyl-N-( lH-pyrazol-l-ylmethyl)-2-ethyl-6-methylaniline, N-chloroacetyl-N-(1H-1,2,4-triazol-l-ylmethy1)-2,6-dimethylaniline, N-chloroacetyl-N-(lH-l,2,4-triazol-l-ylmethy1)-2,6-diethylaniline, N-benzoylmethyl-N-chloroacetyl-2,6-dimethylaniline,
N-benzoylmethy1-N-chloroacety1-2-ethyl-6-methylaniline,
N-chloroacetyl-N-(5-methyl-l,3,4-oxadiazol-2-yl)-2,6-diethylaniline, N-chloroacetyl-N-(5-methyl-l,3,4-oxadiazol-2-yl)-2-ethyl-6-methylaniline, -N-chloroacetyl-N-(5-methyl-l,3,4-oxadiazol-2-y1)-2-tert.-butylaniline, N-chloroacetyl-N-(4-chlorobenzoylmethy1)-2,6-dimethylaniline,
N-chloroacetyl-N-(1-methyl-5-methylthio-l,3,4-triazol-2-ylmethyl)-2,6diethylaniline, ,
N-chloroacety1-N-ethoxymethyl-6-methyl-2-trifluoromethylaniline (Harmony) or
-24N-chloroacetyl-N-acetamidomethyl-2,6-diethylaniline (Amidochlor) as compound of formula I.
4. A composition according to claim 3, containing
N-chloroacetyl-N-methoxymethyl-2,6-diethylaniline (Alachlor),
N-chloroacetyl-N-(2-methoxy-l-methylethy1)-2-ethyl-6-methylaniline (Metolachlor) or
N-chloroacetyl-N-(lH-pyrazol-l-ylmethyl)-2,6-dimethylaniline (Metazachlor) as compound of formula I.
5. A composition according to any one of claims 1 to 4, containing a compound of formula II wherein R5 is Cj-Ci»alkyl or Cj-C«,alkenyl, and each of R6 , R7 , R* and R9 , independently of the others, is hydrogen or Ci~C2alkyl.
6. A composition according to any one of claims 1 to 5, containing a compound of formula II wherein Rs is Ci-Ci»alkyl or C3-Ci,alkenyl, and each of R6, R7, R* and R9 , independently of the others, is hydrogen or methyl.
7. A composition according to any one of claims 1 to 6, containing N-isopropyl-N-chloroacetylcyclohex-1-enamine, N-isopropyl-N-chloroacetyl-3(5)-methylcyclohex-l-enamine, N-isopropyl-N-chloroacetyl-3,5,5(3)-trimethyIcyclohex-1-enamine (Trimexachlor),
N-isopropyl-N-chloroacetyl-3,3,5,5-tetramethylcyclohex-l-enamine or N-allyl-N-chloroacetyl-3,3,5,5-tetramethylcyclohex-I-enamine as compound of formula II.
8. A composition according to claim 1, containing
N-chloroacetyl-N-methoxymethyl-2,6-diethylaniline (Alachlor), ,N-chloroacetyl-N-(2-methoxy-l-methylethy1)-2-ethyl-6-methylaniline (Metolachlor) or
N-chloroacetyl-N-(lH-pyrazo1-1-ylmethy1)-2,6-dimethylaniline (Metazachlor) as compound of formula I and
N-isopropyl-N-chloroacetylcyclohex-l-enamine,
N-isopropyl-N-chloroacetyl-3(5)-methylcyclohex-1-enamine,
-v
BAD ORIGIN***
AP 0 0 0 1 0 6
N-isopropyl-N-chloroacetyl-3,5,5(3)-trimethylcyclohex-l-enamine (Trimexachlor),
N-isopropyl-N-chloroacetyl-3,3,5,5-tetramethylcyclohex-l-enamine or N-allyl-N-chloroacetyl-3,3,5,5-tetramethylcyclohex-l-enamine as compound of formula II.
9. A composition according to claim 8, containing N-chloroacetyl-Nmethoxymethyl-2,6-diethylaniline and N-isopropyl-N-chloroacetyl3,5,5(3)-trimethyIcyclohex-1-enamine.
10. A composition according to claim 8, containing N-chloroacetyl-N(2-methoxy-l-methylethyl)-2-ethy1-6-methylaniline and N-isopropyl-Nchloroacetyl-2,5,5(3)-trimethylcyclohex-l-enamine.
11. A composition according to claim 8, containing N-chloroacetyl-N(lH-pyrazol-l-ylmethyl)-2,6-dimethylaniline and N-isopropyl-N-chloroacetyl-3,5,5(3)-trimethylcyclohex-l-enamine.
12. A method of controlling undesired plant growth, which comprises causing a composition according to any one of claims 1 to 11 to act on the plant to be controlled or on the locus thereof.
13. A method according to claim for controlling weeds in crops·of useful plants.
14. A method according to claim 13 for controlling weeds in maize, rice, sorghum, soya, sugar beet, cotton, sunflower and groundnut crops.
15. Seed that has been dressed with a herbicidally effective amount of a composition according to any one of claims 1 to 11.
APAP/P/1989/000138A 1988-09-02 1989-08-31 Synergistic mixture AP106A (en)

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EP0281521A2 (en) * 1987-03-06 1988-09-07 Ciba-Geigy Ag Herbicidal compositions

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US3586496A (en) * 1969-09-15 1971-06-22 Monsanto Co Herbicidal compositions and use of n-(cycloalken - 1 - yl-) alpha-haloacetamides
GB1283163A (en) * 1970-01-07 1972-07-26 Monsanto Co Herbicidal compositions
FR2479221A1 (en) * 1980-03-25 1981-10-02 Monsanto Co PROCESS FOR PREPARING HETEROCYCLYLMETHYL RADICAL 2-HALOACETAMIDES, NOVEL PRODUCTS THUS OBTAINED AND THEIR USE AS HERBICIDES
BE891248A (en) * 1980-11-26 1982-05-25 Monsanto Co 2-HALOACETAMIDE COMPOUNDS AND HERBICIDE COMPOSITIONS CONTAINING THESE COMPOUNDS AS ACTIVE INGREDIENTS
EP0281521A2 (en) * 1987-03-06 1988-09-07 Ciba-Geigy Ag Herbicidal compositions

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MA21622A1 (en) 1990-04-01
DK434589D0 (en) 1989-09-01
TNSN89093A1 (en) 1991-02-04
NO893526D0 (en) 1989-09-01
AU615571B2 (en) 1991-10-03
JO1588B1 (en) 1989-12-16

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