GB2137092A - Phenoxypropionic Acid Derivatives for Selective Herbicides in Rice Crops - Google Patents
Phenoxypropionic Acid Derivatives for Selective Herbicides in Rice Crops Download PDFInfo
- Publication number
- GB2137092A GB2137092A GB08402921A GB8402921A GB2137092A GB 2137092 A GB2137092 A GB 2137092A GB 08402921 A GB08402921 A GB 08402921A GB 8402921 A GB8402921 A GB 8402921A GB 2137092 A GB2137092 A GB 2137092A
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- United Kingdom
- Prior art keywords
- acid
- formula
- salt
- per hectare
- grams per
- Prior art date
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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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
-
- 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
- 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
- A01N39/04—Aryloxy-acetic 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
- A01N43/34—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
- A01N43/42—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 condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—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
- 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
Abstract
Weeds in rice crops are controlled by the application of an aryloxy- or arylimino-phenoxypropionic acid or a salt, ester or amide thereof in association with hormone weed killers known under the designations MCPA; 2,4-D; 2,4-DB; MCPB; 2,4,5-T; mecoprop; and dichloroprop or the salts, esters and amides thereof.
Description
SPECIFICATION
Herbicidal Process
This invention relates to herbicidal processes, and to herbicidal compositions for use therein.
In recent years a variety of novel herbicides has been proposed for selective control of grass weeds growing in a broad-leaved crop. In terms of chemical structure many of these compounds are aryloxy- or aryliminophenoxypropionic acids of the general formula (I):
wherein Ar may be a substituted benzene ring or a substituted mono- or bicyclic heterocyclic ring and
X is oxygen or an NH group or an imino group bearing a further substituent. The substituted phenoxypropionic acids may be used as herbicides in the form of the free acids (preferably in admixture with a diluent or carrier, and with adjuvants such as surface-active agents) or may be used in the form of their functional derivatives (e.g. salts, esters or amides of the acids), similarly in conjunction with appropriate adjuvants.
Examples of these aryloxyphenoxypropionic and aryliminophenoxypropionic acids include the following:
1. Pyridyloxyphenoxypropionic acids of the formula (II)
wherein Z and Y each represent hydrogen, halogen, or a CF3, CF2H, or CICF2- radical, provided that at least one of Z and Y is a halogenomethyl radical.
Compounds of this class and their salts, esters and amides, are described in UK Patent
Application No. 2002368A published 21 February 1 979, the contents of which are hereby incorporated by reference. The present invention contemplates the use of any of the compounds of formula (II) disclosed in UK 2002368A.
A particularly suitable compound for use in the present invention is the compound of formula (III), having the common name fluazifop-butyl
2. 1 ,2,4-Benzotriazinylaminophenoxypropionic acids of the formula (IV)
optionally substituted in the benzene ring of the benzotriazinyl radical, and N-oxides, salts, esters and amides thereof. Compounds of this class are described in European Patent Application 24931 published on 11 March 1981, the contents of which are hereby incorporated by reference. Particular examples of compounds of this type include those of formula (V) and (Vl)
wherein R is ethyl, propyl, or sec-butyl.
3. Quinoxalyloxyphenoxypropionic acids of the formula (VII)
optionally substituted in the benzene ring of the quinoxalinyl radical, and the 1 4-linked benzene ring and their N-oxides, salts, esters, and amides. Compounds of this class are described in European Patent
Application 23785 published on 11 February 1981 and in UK Patent Application No. 2042539A, the contents of which are herein incorporated by reference. Particular examples of compounds of this class include those of formula (VIII) in which Z is hydrogen or fluorine:
4. Quinolinyloxyphenoxypropionic acids of the formula (IX):
optionally substituted in the benzene ring of the quinolyl radical, and their N-oxides, salts, esters, and amides.
Compounds of this type are described in European Patent Application No. 2931 9 published 27
May 1 981 the contents of which are herein incorporated by reference. Particular examples of compounds of this class include those of formula (X) below:
wherein X is chlorine or fluorine.
5. Benzothiazolyioxyphenoxypropionic acids and benzoxazolyloxyphenoxypropionic acids of the formula (XI)
wherein X is oxygen or sulphur, optionally substituted in the benzene ring of the benzothiazoyl- or benzoazolyl radical, and their salts, esters and amides. Compounds of this class are described in UK
Patent Application No. 2046753A, the contents of which are herein incorporated by reference.
Particular examples of compounds of this class include those of the formula (XII)
wherein X is oxygen or sulphur.
6. Benzothiazolyliminophenoxypropionic acids and benzoxazolyiiminophenoxypropionic acids of the formula (XIII)
wherein X is oxygen or sulphur, optionally substituted in the benzene ring of the benzthiazoyl or benzoxazolyl radical. Compounds of this type are described in US Patent 4,31 4,065, published 2
February 1982, the contents of which are herein incorporated by reference. A particular example of a compound of this class is the compound of formula (XIV) below:
7. Substituted 4(phenylamino)phenoxypropionic acids of formula (XV)
and their salts, esters, and amides, wherein X represents a variety of possible substituents including halogen, and nitro, and n is an integral number from 1 to 5.Compounds of this class are described in
European Patent Application No. 13144 published 9 September 1980 and in Belgian Patent 876077 the contents of which are herein incorporated by reference. A particular example of a compound of this type is the compound of formula (XVI)
It will be understood by those skilled in the art that the compounds listed above are capable of existing in stereoisomeric forms, since the propionic acid moiety in each compound contains an asymmetric carbon atom. In general the D isomer in each of these compounds is more herbicidally active than the L isomer. The present invention contemplates the use of the separated D isomer as well as the racemic mixture of D and L compounds and mixtures of the D and L forms in unequal proportions.
According to the present invention there is provided a method of selectively controlling weeds growing in rice crops, which comprises applying to the crop area a herbicidal amount of an aryloxy- or arylimino-phenoxy-propionic acid of formula:
wherein Ar is a substituted benzene ring or a substituted mono- or bicyclic ring; and
X is oxygen or an NH group or an imino group bearing a further substituent; or a salt, ester or amide of said aryloxy- or aryliminophenoxypropionic acid of formula (I) in association with a hormone weed killer which is one or more of the 2-(phenoxy)alkanoic acid herbicides known under the designations MCPA; 2,4-D; 2,4-DB; MCPE3; 2,4,5-T; mecoprop; or dichloroprop or the salts, esters and amides thereof.
The application to the crop area preferably takes place after emergence of the crop.
By hormone weed-killer we mean the 2(phenoxy)alkanoic acid herbicides known under the designations MCPA, 2,4-D, 2,4-DB, MCPB, 2,4,5-T, mecoprop, and dichlorprop, and their salts, esters, and amides. MCPA and 2,4-D and their salts esters or amides are especially preferred hormone weedkillers.
The proportions in which the aryloxy- or aryliminophenoxypropionic acid and the hormone weedkiller are used will vary somewhat according to the particular compounds chosen for use. In general, however, the amount of the aryloxy- or arylimino-phenoxypropionic acid will be from 5 to 100 grams per hectare and the amount of the hormone weed-killer will be from 200 to 1000 grams per hectare (e.g. from 400 to 800 g/ha).
Surprisingly, the effect of applying the aryloxy- or arylimino-phenoxypropionic acid in admixture with a hormone weed-killer is to reduce the damage to the rice crop caused by the aryloxy- or arylimino-phenoxypropionic acid, without causing significant loss of herbicidal activity of the latter compounds against the grass weeds. Furthermore, the herbicidal activity of the hormone weed-killers against the broad-leaved weeds in the rice crop is not appreciably diminished.
A preferred method of controlling weeds in rice crops according to the invention comprises the application of a pyridyloxyphenoxypropionic acid of formula (II) in association with a hormone weedkiller. Preferably there is used an amount of from 50 to 100 grams of pyridyloxyphenoxypropionic acid per hectare, in admixture with from 300 to 500 grams per hectare of hormone weed-killer which is preferably MCPA or 2,4-D. Preferably the pyridyloxyphenoxypropionic acid is the compound of formula (III) above.
The mixtures of herbicides in the method of the invention may be applied to the crop area by dispersing the active ingredients in water together with appropriate adjuvants, and spraying the dispersion on the crop area. Appropriate adjuvarits include for example surface-active agents.
Surface active agents may be of the cationic, anionic or non-ionic type. Suitable agents of the cationic type include for example quaternary ammonium compounds, for example cetyltrimethyl ammonium bromide. Suitable agents of the anionic type include for example soaps, salts of aliphatic mono-esters of sulphuric acid, for example sodium lauryl sulphate; and salts of sulphonated aromatic compounds, for example dodecyl-benzenesulphonate, sodium, calcium and ammonium lignosulphonate, butylnaphthalene sulphonate, and a mixture of the sodium salts of diisopropyl- and triisopropyl-naphthalenesulphonic acid. Suitable agents of the non-ionic type include, for example, the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol and cetyl alcohol, or with alkyl phenols such as octylphenol, nonylphenol, and octylcresol.Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, for example sorbitol monolaurate; the condensation products of the said partial esters with ethylene oxide and the lecithins.
Certain of the mixtures of aryloxy- or aryliminophenoxy acids or their salts, esters, or amides with the hormone in weed-killers are novel mixtures in themselves and form a further part of the invention.
The method of the invention is now illustrated by the following Examples.
EXAMPLE 1
This Example illustrates the selective control of grass weeds and broad-leaved weeds growing in a rice crop, according to the invention, by reference to a field trial carried out in Luzon, in the
Phillippines.
In the field trial rice plants (variety IR36) were transplanted to a series of plots (2 metres by 2.5 metres). Eight days after transplanting, the plots were sprayed with fluazifop-butyl, MCPA salt, 2,4-D salt, and 2,4-D ester separately and in the combinations shown in Table I below.
TABLE I
Percentage Weed Control 32 DAT Compound Applied Percentage Damage (Grams per Hectare) to Rice 5 DAT* E. glabrescens M. vaginalis Fluazifop-butyl (63) 1 7 100 43 MCPA salt (400) 0 47 100 2,4-D salt (400) 0 60 100 2,4-D ester (400) 0 40 100 Fluazifop-butyl (63)+ O 100 MCPA salt (400) Fluazifop-butyl (63)+ O 100 2,4-D salt (400) Fl uazifop-butyl + O -100 100 2,4-D ester (400) * DAT=Days after treatment.
Notes
The spray volume for all applications was 500 litres per hectare. The spray treatments were made up from commercially available products as follows:
Fluazifop-butyl- from "Fusilade", a formulation of fluazifop-butyl containing 25% of the active ingredient. MCPA salt-from "Agroxone", a formulation containing sodium and potassium salts of
MCPA in equal amounts. 2,4-D salt- from "Fernimine" M, containing 2,4-D as its dimethylamine salt.
2,4-D ester: The isoctyl ester of 2,4-D.
The final spray solution for each treatment contained 0.1% of Agral 90, a surfactant comprising a condensate of from seven to eight molar proportions of ethylene oxide with p-nonyl phenol.
The weed species for which results are given above were Echinochloa glabrescens and Monochioria vaginalis.
From the above table it can be seen that fluazifop-butyl gave good control of the grass weed (E.
glabrescens) but poor broad-leaved control (M. vaginalis), with slight damage to rice.
The hormone weed-killers MCPA, 2,4-D salt and 2,4-D ester gave poor control of the grass weed but good broad-leaved control with no damage to rice. All mixtures of fluazifop-butyl with a hormone herbicide gave good control of both grass and broad-leaved weed with no damage to rice. Thus the effect of mixing the hormone weed-killers with fluazifop-butyl was to overcome the slightly damaging effect of the latter compound on the crop without reducing its efficacy on the grass weed at the doses used here. Moreover, fluazifop-butyl did not reduce the effect of the hormone weed-killer on the broadleaved weed.
EXAMPLE 2
This Example further illustrates the selective control according to the invention of grass and broad-leaved weeds growing in a rice crop.
A further field trial was carried out as described in Example 1, but in which the rice crop was sprayed seven days after transplantation. The results of the trial are given in Table 2 below. The abbreviation FB stands for fluazifop-butyl.
TABLE 2
Percentage Weed Control 33 DAT Compound Applied Percentage Damage (Grams per Hectare) to Rice 6 DAT4 E. glabrescens M. vaginalis FB (25) 0 30 0 FB (25)+MCPA (400) 0 30 47 FB (50) 0 100 0 F B (50)+MCPA (400) 0 93 93 Fib(100) 30 100 0 FB(100)+MCPA(400) 13 100 100 MCPA (400) 3 23 77 EXAMPLE 3
This Example further illustrates the selective control according to the invention of grass and broad-leaved weeds growing in a rice crop.A further field trial was carried out as described in Example 1 except that in this trial, the rice crop was paddy rice grown from seed and sprayed seven days after the rice had been sown. The results are given in Table 3 below.
TABLE 3
Percentage Weed Control 33 DAT Compound Applied Percentage Damage (Grams per Hectare) to Rice 5 DAT* E. glabrescens M. vaginalis FB(25) 0 70 37 FB (25)+MCPA (400) 13 40 100 FB (50) 17 100 0 FB (50)+MCPA (400) 3 90 100 FB(100) 30 100 0 FB (100)+MCPA (400) 0 100 100 MCPA (400) 0 20 93 It will be seen from the above Table that fluazifop-butyl when used alone was slightly more damaging on the seeded rice than it was on the transplanted rice used in the trials for which results are given in Examples 1 and 2. However, the improved selectivity obtained by admixture with MCPA is again evident in this trial. Thus, at the dose of 50-1 00 g/ha of fluazifop-butyl mixed with 400 g/ha of
MCPA, the reduction in damage on the crop (14%, 30% respectively) were appreciably greater than the reduction in efficacy of Echinochloa control (10%, 0% respectively).
Claims (7)
1. A method of selectively controlling weeds growing in rice crops, which comprises applying to the crop area a herbicidal amount of an aryloxy- or arylimino-phenoxy-propionic acid of formula:
wherein Ar is a substituted benzene ring or a substituted mono- or bicyclic ring; and
X is oxygen or an NH group or an imino group bearing a further substituent; or a salt, ester or amide of said aryloxy- or arylimino-phenoxypropionic acid of formula (I) in association with a hormone weed killer which is one or more of the 2-(phenoxy)alkanoic acid herbicides known under the designation MCPA; 2,4-D; 2,4-DB; MCPB; 2,4,5-T; mecoprop; or dichloroprop or the salts, esters and amides thereof.
2. A method according to claim 1 wherein there is applied to the crop area, after the emergence of the crop, a herbicidal amount of an aryloxyphenoxypropionic acid which is a pyridyloxyphenoxypropionic acid of formula:
wherein Z and Y each represent hydrogen, halogen or CF3, CF2H, or CICF2- radical, provided that at least one of Z and Y is a halogenomethyl radical or a salt, ester or amide of said pyridyloxyphenoxypropionic acid of formula (II).
3. A method according to claim 2 wherein there is used a pyridylphenoxypropionic acid of formula:
or a salt, ester or amide thereof.
4. A method according to any of the preceding claims wherein the aryloxy- or aryliminophenoxypropionic acid is used in an amount of from 5 to 100 grams per hectare and the hormone weed killer is used in an amount of from 200 to 1000 grams per hectare.
5. A method according to claim 4 wherein the hormone weedkiller is used in an amount of from 400 to 800 grams per hectare.
6. A method according to claim 2 or 3 wherein the pyridylphenoxypropionic acid is used in an amount of from 50 to 1 00 grams per hectare in admixture with from 300 to 500 grams per hectare of the hormone weed killer.
7. A method according to any of the preceding claims wherein the hormone weed killer is a 2 (phenoxy)alkanoic acid herbicides known under the designations MCPA or 2,4-D or a salt, ester and amide thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08402921A GB2137092A (en) | 1983-02-28 | 1984-02-03 | Phenoxypropionic Acid Derivatives for Selective Herbicides in Rice Crops |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838305500A GB8305500D0 (en) | 1983-02-28 | 1983-02-28 | Herbicidal process |
| GB08402921A GB2137092A (en) | 1983-02-28 | 1984-02-03 | Phenoxypropionic Acid Derivatives for Selective Herbicides in Rice Crops |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8402921D0 GB8402921D0 (en) | 1984-03-07 |
| GB2137092A true GB2137092A (en) | 1984-10-03 |
Family
ID=26285380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08402921A Withdrawn GB2137092A (en) | 1983-02-28 | 1984-02-03 | Phenoxypropionic Acid Derivatives for Selective Herbicides in Rice Crops |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2137092A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0186971A1 (en) * | 1984-11-28 | 1986-07-09 | Ivon Watkins-Dow Limited | Herbicidal compositions and methods |
| US4668276A (en) * | 1984-02-08 | 1987-05-26 | Hoechst Aktiengesellschaft | Use of aryloxy compounds as antidotes |
| US4929271A (en) * | 1986-12-23 | 1990-05-29 | May & Baker Limited | Herbicidal method using diflufenican |
| EP0525474A2 (en) * | 1991-07-12 | 1993-02-03 | Hoechst Schering AgrEvo GmbH | Synergistic herbicidal agents |
| EP0612472A1 (en) * | 1993-02-26 | 1994-08-31 | Monsanto Europe S.A./N.V. | Herbicidal combinations comprising triazole derivatives (III) |
| WO2000003591A2 (en) * | 1998-07-16 | 2000-01-27 | Aventis Cropscience Gmbh | Herbicides |
| CN104255728A (en) * | 2014-03-29 | 2015-01-07 | 潍坊先达化工有限公司 | Application of 2,4-dichlorophenoxybutyric acid and derivative of 2,4-dichlorophenoxybutyric acid |
-
1984
- 1984-02-03 GB GB08402921A patent/GB2137092A/en not_active Withdrawn
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4668276A (en) * | 1984-02-08 | 1987-05-26 | Hoechst Aktiengesellschaft | Use of aryloxy compounds as antidotes |
| EP0186971A1 (en) * | 1984-11-28 | 1986-07-09 | Ivon Watkins-Dow Limited | Herbicidal compositions and methods |
| US4929271A (en) * | 1986-12-23 | 1990-05-29 | May & Baker Limited | Herbicidal method using diflufenican |
| TR28811A (en) * | 1991-07-12 | 1997-04-07 | Hoechst Ag | Synergistic herbicidal agents against monocotyl and dicotyl weeds. |
| EP0525474A3 (en) * | 1991-07-12 | 1993-08-11 | Hoechst Ag | Synergistic herbicidal agents |
| EP0525474A2 (en) * | 1991-07-12 | 1993-02-03 | Hoechst Schering AgrEvo GmbH | Synergistic herbicidal agents |
| US5650375A (en) * | 1991-07-12 | 1997-07-22 | Hoechst Aktiengesellschaft | Synergistic herbicidal compositions |
| US5872077A (en) * | 1991-07-12 | 1999-02-16 | Hoechst Aktiengesellschaft | Synergistic herbicidal compostitions |
| EP0612472A1 (en) * | 1993-02-26 | 1994-08-31 | Monsanto Europe S.A./N.V. | Herbicidal combinations comprising triazole derivatives (III) |
| WO2000003591A2 (en) * | 1998-07-16 | 2000-01-27 | Aventis Cropscience Gmbh | Herbicides |
| WO2000003591A3 (en) * | 1998-07-16 | 2000-06-22 | Aventis Cropscience Gmbh | Herbicides |
| US8357629B2 (en) | 1998-07-16 | 2013-01-22 | Bayer Cropscience Ag | Herbicidal compositions |
| US8765638B2 (en) | 1998-07-16 | 2014-07-01 | Bayer Intellectual Property Gmbh | Herbicidal compositions |
| US8791050B2 (en) | 1998-07-16 | 2014-07-29 | Bayer Intellectual Property Gmbh | Herbicidal compositions |
| CN104255728A (en) * | 2014-03-29 | 2015-01-07 | 潍坊先达化工有限公司 | Application of 2,4-dichlorophenoxybutyric acid and derivative of 2,4-dichlorophenoxybutyric acid |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8402921D0 (en) | 1984-03-07 |
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