WO1994027438A1 - Herbicidal compositions - Google Patents

Herbicidal compositions Download PDF

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Publication number
WO1994027438A1
WO1994027438A1 PCT/EP1994/001669 EP9401669W WO9427438A1 WO 1994027438 A1 WO1994027438 A1 WO 1994027438A1 EP 9401669 W EP9401669 W EP 9401669W WO 9427438 A1 WO9427438 A1 WO 9427438A1
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WO
WIPO (PCT)
Prior art keywords
dicamba
als
metsulfuron
chlorimuron
inhibitor herbicide
Prior art date
Application number
PCT/EP1994/001669
Other languages
French (fr)
Inventor
Mark Caroll Boyles
Bart Aloysaus Brinkman
John Melvin Fenderson
Original Assignee
Sandoz Ltd.
Sandoz-Patent-Gmbh
Sandoz-Erfindungen Verwaltungsgesellschaft M.B.H.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sandoz Ltd., Sandoz-Patent-Gmbh, Sandoz-Erfindungen Verwaltungsgesellschaft M.B.H. filed Critical Sandoz Ltd.
Priority to AU69964/94A priority Critical patent/AU6996494A/en
Publication of WO1994027438A1 publication Critical patent/WO1994027438A1/en

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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
    • 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
    • A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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

Definitions

  • the present invention concerns a method of controlling undesired plant growth employing co-application of dicamba and an amino acid synthesis (ALS) inhibitor herbicide.
  • dicamba and an amino acid synthesis (ALS) inhibitor herbicide.
  • ALS amino acid synthesis
  • ALS inhibitor herbicides include sulfonylureas such as rimsulfuron (DPX 9636), metsulfuron, metsulfuron-methyl, ethametsulfuron, nicosulfuron, triasulfuron, primisulfuron, bensulfuron, chlorimuron, chlorimuron-ethyl, chlorsulfuron, sulfometuron, thifensulfuron, tribenuron, triflusulfuron, clopyrasulfuron, and pyrazasulfuron; sulfonamides such as flumetsulam (DE498); and imidazolinones such as imazaquin, imazamethabenz, imazapyr, imazmethapyr and imazethapyr.
  • sulfonylureas such as rimsulfuron (DPX 9636), metsulfuron, metsulfuron-methyl, eth
  • This invention therefore concerns a method for reducing phytotoxicity to crop plants due to ALS-inhibitor herbicides which comprises co-applying to the crop or to the locus thereof dicamba with said ALS-inhibitor herbicide.
  • Co-application can be achieved using tank mixes of preformulated individual active ingredients, simultaneous or sequential (preferably 1-2 days) application of such formulations or application of preformulated fixed pre-mix combinations of the individual active ingredients.
  • Dicamba is particularly suitable in the control of annual and perennial broadleaf weeds especially in post-emergent application and is selective in certain crops, especially com and sorghum.
  • ALS inhibitors are active against a broad spectrum of both broadleaf and grassy weeds. Selectivity can be found in a wide range of individual crops depending upon the precise structure of the compound for example in the case of imidazolinones and sulfonylureas.
  • co-application according to the invention is particularly useful when employed for the control of weeds where ALS inhibitor herbicides such as sulfonylureas, sulfonamides and imidazolinones are employed in grassy crops such as sorghum, com and wheat.
  • ALS inhibitor herbicides such as sulfonylureas, sulfonamides and imidazolinones
  • dicamba reduces possible phytotoxic effects of the ALS inhibitors herbicides.
  • Preferred ALS inhibitors for use according to the invention are metsulfuron (-methyl), nicosulfuron, triasulfuron, primisulfuron, chlorimuron (-ethyl), chlorsulfuron, thifensulfuron, rimsulfuron, imazethapyr and imazmethapyr.
  • dicamba with, for example, metsulfuron (-methyl), imazethapyr, triasulfuron, thifensulfuron, imazmethapyr, nicosulfuron, primisulfuron, rimsulfuron, chlorimuron (-ethyl), chlorsulfuron.
  • Examples of commercial forms of these preferred herbicides include dicamba - BANVEL ® metsulfuron-methyl — ALLY ® imazethapyr - PURSUIT ® triasulfuron - AMBER ® thifensulfuron - PINNACLE ® imazmethapyr - CADRE ® nicosulfuron - ACCENT ® primisulfuron - BEACON ® rimsulfuron - TITUS ® chlorimuron - CLASSIC ® chlorsulfuron - GLEAN ®
  • the application rates of the herbicides employed in co-application will of course depend on the active ingredients chosen, the weed to be controlled, the crop plant involved, soil type, season, climate, soil ecology and various other factors. Optimum usage is readily determinable by one skilled in the art using routine testing such as greenhouse or small plot testing. Application rates will usually be those recommended for use of commercially available forms of the active ingredients.
  • the weight ratio of dicamba with a sulfonylurea lies conveniently within the range of from 50:1 to 500:1, especially 100:1 to 300:1.
  • Co-applied herbicides when formulated individually or as preformulated fixed pre-mixes are conveniently employed in association with agriculturally acceptable diluents or carriers.
  • a typical co-application of dicamba (a) with metsulfuron-methyl (x) would be e.g. from 50 to 500 gm/ha; especially 100 to 300 gm/ha of (a) and 0.5 to 10 gm/ha; especially 1 to 5 gm/ha of (x).
  • Suitable formulations contain from 0.01 to 99% by weight of active ingredient(s), and from 1 to 99.99% of solid or liquid diluent(s) and other additives e.g. surfactants. Higher ratios of surfactant to active ingredient(s) are sometimes desirable and are achieved by incorporation into the formulation or at tank mixing.
  • Application forms of a composition generally contain between 0.01 and 25% by weight of active ingredient(s). Lower or higher levels of active ingredient(s) can, of course, be present depending on the intended use, the physical properties of the compound and the mode of application. Concentrate forms of a composition intended to be diluted before use generally contain between 5 and 95%, preferably between 10 and 81% by weight of active ingredient(s).
  • Useful formulations of the active ingredients either alone or in combination include dusts, granules, suspension concentrates, wettable powders, flowables and the like. They are obtained by conventional manner, e.g. by mixing an active ingredient(s) each optionally as twin packs with the diluent(s) and optionally with other ingredients.
  • the active ingredients may be used in microencapsulated form.
  • Agriculturally acceptable additives may be employed in the herbicidal compositions to improve the performance of the active ingredient and to reduce foaming, caking and corrosion, for example.
  • surfactant as used herein means an agriculturally acceptable material which imparts emulsifiability, spreading, wetting, dispersibility or other surface-modifying properties.
  • surfactants are lignin sulfonates, and fatty acid sulfonates, e.g. lauryl sulfonate, the condensation product of formaldehyde with naphthalene sulfonate, an alkylarylsulfonate, an ethoxylated alkylphenol, an ethoxylated fatty alcohol and the like.
  • Dusts or granules means a liquid or solid agriculturally acceptable material used to dilute a concentrated material to a usable or desirable strength.
  • talc kaolin or diatomaceous earth
  • liquid concentrate forms for example a hydrocarbon such as xylene or an alcohol such as isopropanol, and for liquid application forms e.g. diesel oil or preferably water.
  • compositions of the invention can also comprise other compounds having biological activity, e.g. other compounds having a similar or complementary herbicidal or antidotal activity or compounds having fungicidal, insecticidal, or other pesticidal activity.
  • Solid forms for compositions are preferred from the point of view of environmentally innocuous packaging.

Abstract

Co-application of dicamba and amino acid synthesis (ALS) inhibitor herbicides reduce the incidence of phytotoxic effects, particularly in grassy crops.

Description

HERBICIDAL COMPOSITIONS
The present invention concerns a method of controlling undesired plant growth employing co-application of dicamba and an amino acid synthesis (ALS) inhibitor herbicide.
Examples of ALS inhibitor herbicides include sulfonylureas such as rimsulfuron (DPX 9636), metsulfuron, metsulfuron-methyl, ethametsulfuron, nicosulfuron, triasulfuron, primisulfuron, bensulfuron, chlorimuron, chlorimuron-ethyl, chlorsulfuron, sulfometuron, thifensulfuron, tribenuron, triflusulfuron, clopyrasulfuron, and pyrazasulfuron; sulfonamides such as flumetsulam (DE498); and imidazolinones such as imazaquin, imazamethabenz, imazapyr, imazmethapyr and imazethapyr.
The above mentioned herbicides, processes for their production, herbicidal compositions containing them and their use as herbicides are known in the art and are described e.g. in the Pesticide Manual, 9th edition (1991), The British Crop protection Council, London and/or in Ag Chem New Product Review, Ag Chem Information Services, Indianapolis, Indiana and/or in Crop Protection Chemicals Reference, Chemical and Pharmaceutical Press (c/o John Wiley NY, NY) and/or in Farm Chemicals Handbook, Master Publishing Co., Willoughby, Ohio, each published annually or similar publications.
It has now surprisingly been found that co-application of dicamba and an ALS inhibitor herbicide results in a reduction of the phytotoxic effects of the latter particularly on grassy crops such as sorghum, corn and wheat without a corresponding reduction of effectiveness in the control of undesired plant growth.
This invention therefore concerns a method for reducing phytotoxicity to crop plants due to ALS-inhibitor herbicides which comprises co-applying to the crop or to the locus thereof dicamba with said ALS-inhibitor herbicide. Co-application can be achieved using tank mixes of preformulated individual active ingredients, simultaneous or sequential (preferably 1-2 days) application of such formulations or application of preformulated fixed pre-mix combinations of the individual active ingredients.
Dicamba is particularly suitable in the control of annual and perennial broadleaf weeds especially in post-emergent application and is selective in certain crops, especially com and sorghum.
ALS inhibitors are active against a broad spectrum of both broadleaf and grassy weeds. Selectivity can be found in a wide range of individual crops depending upon the precise structure of the compound for example in the case of imidazolinones and sulfonylureas.
As mentioned above co-application according to the invention is particularly useful when employed for the control of weeds where ALS inhibitor herbicides such as sulfonylureas, sulfonamides and imidazolinones are employed in grassy crops such as sorghum, com and wheat. In such uses co-application according to the invention with dicamba reduces possible phytotoxic effects of the ALS inhibitors herbicides.
Preferred ALS inhibitors for use according to the invention are metsulfuron (-methyl), nicosulfuron, triasulfuron, primisulfuron, chlorimuron (-ethyl), chlorsulfuron, thifensulfuron, rimsulfuron, imazethapyr and imazmethapyr.
Particularly preferred combinations are thus dicamba with, for example, metsulfuron (-methyl), imazethapyr, triasulfuron, thifensulfuron, imazmethapyr, nicosulfuron, primisulfuron, rimsulfuron, chlorimuron (-ethyl), chlorsulfuron. Examples of commercial forms of these preferred herbicides include dicamba - BANVEL® metsulfuron-methyl — ALLY® imazethapyr - PURSUIT® triasulfuron - AMBER® thifensulfuron - PINNACLE® imazmethapyr - CADRE® nicosulfuron - ACCENT® primisulfuron - BEACON® rimsulfuron - TITUS® chlorimuron - CLASSIC® chlorsulfuron - GLEAN®
The application rates of the herbicides employed in co-application will of course depend on the active ingredients chosen, the weed to be controlled, the crop plant involved, soil type, season, climate, soil ecology and various other factors. Optimum usage is readily determinable by one skilled in the art using routine testing such as greenhouse or small plot testing. Application rates will usually be those recommended for use of commercially available forms of the active ingredients.
In general, for example, satisfactory results are obtained when co-applying at rates of 50 to 2000 gm/ha especially 250 to 1000 gm/ha of dicamba and 0.5 to 64 gm ha especially 1 to 30 gm/ha of a sulfonylurea herbicide or 100 to 3000, especially 150 to 1000 gm/ha of an imidazolinone herbicide.
In general, for example, the weight ratio of dicamba with a sulfonylurea lies conveniently within the range of from 50:1 to 500:1, especially 100:1 to 300:1.
Co-applied herbicides when formulated individually or as preformulated fixed pre-mixes are conveniently employed in association with agriculturally acceptable diluents or carriers.
Methods of preparing herbicidal formulations are described in the literature along with suitable liquid and solid carriers such as in USP 4,192,669 and 4,163,661 which are incorporated herein by reference.
A typical co-application of dicamba (a) with metsulfuron-methyl (x) would be e.g. from 50 to 500 gm/ha; especially 100 to 300 gm/ha of (a) and 0.5 to 10 gm/ha; especially 1 to 5 gm/ha of (x).
Details of weed spectra, selectivity, application rates and regimes and the like for individual active ingredients which may be employed according to the invention are also disclosed in the various references cited above.
Suitable formulations contain from 0.01 to 99% by weight of active ingredient(s), and from 1 to 99.99% of solid or liquid diluent(s) and other additives e.g. surfactants. Higher ratios of surfactant to active ingredient(s) are sometimes desirable and are achieved by incorporation into the formulation or at tank mixing. Application forms of a composition generally contain between 0.01 and 25% by weight of active ingredient(s). Lower or higher levels of active ingredient(s) can, of course, be present depending on the intended use, the physical properties of the compound and the mode of application. Concentrate forms of a composition intended to be diluted before use generally contain between 5 and 95%, preferably between 10 and 81% by weight of active ingredient(s).
Useful formulations of the active ingredients either alone or in combination include dusts, granules, suspension concentrates, wettable powders, flowables and the like. They are obtained by conventional manner, e.g. by mixing an active ingredient(s) each optionally as twin packs with the diluent(s) and optionally with other ingredients.
Alternatively, the active ingredients may be used in microencapsulated form. Agriculturally acceptable additives may be employed in the herbicidal compositions to improve the performance of the active ingredient and to reduce foaming, caking and corrosion, for example.
"Surfactant" as used herein means an agriculturally acceptable material which imparts emulsifiability, spreading, wetting, dispersibility or other surface-modifying properties. Examples of surfactants are lignin sulfonates, and fatty acid sulfonates, e.g. lauryl sulfonate, the condensation product of formaldehyde with naphthalene sulfonate, an alkylarylsulfonate, an ethoxylated alkylphenol, an ethoxylated fatty alcohol and the like.
"Diluent" as used herein means a liquid or solid agriculturally acceptable material used to dilute a concentrated material to a usable or desirable strength. For dusts or granules it can be e.g. talc, kaolin or diatomaceous earth, for liquid concentrate forms for example a hydrocarbon such as xylene or an alcohol such as isopropanol, and for liquid application forms e.g. diesel oil or preferably water.
For co-application for example as tank mixes or in sequential treatment commercially available forms of the active ingredients may be employed.
The compositions of the invention can also comprise other compounds having biological activity, e.g. other compounds having a similar or complementary herbicidal or antidotal activity or compounds having fungicidal, insecticidal, or other pesticidal activity.
Solid forms for compositions are preferred from the point of view of environmentally innocuous packaging.
The following examples illustrate the practice of the invention. EXAMPLE 1
Field trials are conducted on five leaf sorghum to determine crop injury (≡herbicide tolerance) and pigweed control. Products employed were ALLY® (metsulfuron-methyl; DuPont) in the commercially available 60% dry flowable form; BANVEL® (dicamba- DMA; Sandoz) in the 40% dicamba equivalent commercial form; 2,4-D (as 2,4-D-DMA 4SL=480 g a.i./L) and MARKSMAN® (dicamba-DMA + atrazine; Sandoz).
Application takes place post-emergent over the top when pigweed is 2" tall. Evaluations are carried out at from 1 to 6 weeks after treatment (WAT).
RESULTS
SORGHUM:TOLERANCE - STUNT/PIGWEED CONTROL
Active Appl. Rate Sorghum Inj. Pigweed Cont, Ingredient gm a.i./ha % %
ALLY® 2.1 18 85 ALLY® + 2.1 + 13 94
2,4-D 280 ALLY® + 2.1 + 7 92
BANVEL® 280 ALLY® + 2.1 + 7 83
MARKSMAN® 896
ALLY® 1.05 13 76 ALLY® + 1.05 + 4 93
2,4-D 280 ALLY® + 1.05 + 5 96
BANVEL® 280 ALLY® + 1.05 + 3 75
MARKSMAN® 896
/
2,4-D 280 4 67
BANVEL® 280 2 83
MARKSMAN® 896 0 90 Application of ALLY® alone at both rates tested produced unacceptable stunt in sorgum. Co-application of ALLY® with 2,4-D, BANVEL® or MARKSMAN® reduced stunting without reducing weed control.
The optimum balance between reduced sorghum stunt and excellent pigweed control was shown by the combination of ALLY® and BANVEL® at both rates tested.

Claims

WHAT IS CLAIMED IS:
1. A method for reducing phytotoxicity of ALS-inhibitor herbicides to crop plants, which comprises co-applying to the crop plants or to the locus thereof a phytotoxicity reduction effective amount of dicamba together with a herbicidally effective amount of said ALS-inhibitor herbicide.
2. A method of selectively controlling unwanted plant growth in grassy crops which comprises co-application to the locus of said unwanted plant growth at least one amino acid synthesis inhibitor herbicide in an herbicidally effective amount and dicamba in a herbicidally and phytotoxicity reduction effective amount.
3. A method of controlling unwanted plant growth which comprises co-application to the locus of the said unwanted plant growth dicamba and at least one amino acid synthesis inhibitor herbicide in herbicidally effective aggregate amount.
4. A method according to any one of Claims 1 to 3 wherein the ALS inhibitor herbicide is selected from a sulfonylurea such as rimsulfuron, metsulfuron, metsul¬ furon-methyl, ethametsulfuron, nicosulfuron, triasulfuron, primisulfuron, bensulfuron, chlorimuron chlorimuron-ethyl, chlorsulfuron, sulfometuron, thifen¬ sulfuron, tribenuron, triflusulfuron, clopyrasulfuron or pyrazasulfuron, a sulfonamide such as flumetsulam or an imidazolinone such as imazaquin, imazamethabenz, imazapyr, imazmethapyr or imazethapyr.
5. A method according to any one of Claims 1 to 3 wherein the ALS inhibitor herbicide is selected from metsulfuron (-methyl), nicosulfuron, triasulfuron, primisulfuron, chlorimuron (-ethyl), chlorsulfuron, thifensulfuron, rimsulfuron, imazmethapyr or imazethapyr.
6. A method according to any one of Claims 1 to 3 wherein the amount of dicamba is from 50 to 2000 gm ha.
7. A method according to any one of Claims 1 to 3 wherein the amount of ALS inhibitor herbicide is from 0.5 to 64 gm/ha of a sulfonylurea herbicide or from 100 to 3000 gm/ha of an imidazolinone herbicide.
8. A herbicidal composition comprising a herbicidally effective aggregate amount of dicamba and an amino acid synthesis (ALS) inhibitor herbicide.
9. A herbicidal composition according to Claim 8 wherein the ALS inhibitor herbicide is selected from a sulfonylurea such as rimsulfuron, metsulfuron, metsulfuron- methyl, ethametsulfuron, nicosulfuron, triasulfuron, primisulfuron, bensulfuron, chlorimuron, chlorimuron-ethyl, chlorsulfuron, sulfometuron, thifensulfuron, tri- benuron, triflusulfuron, clopyrasulfuron or pyrazasulfuron, a sulfonamide such as flumetsulam or an imidazolinone such as imazaquin, imazamethabenz, imazapyr, imazmethapyr or imazethapyr.
10. A herbicidal composition according to Claim 8 wherein the ALS inhibitor herbicide is selected from metsulfuron (-methyl), nicosulfuron, triasulfuron, primisulfuron, chlorimuron (-ethyl), chlorsulfuron, thifensulfuron, rimsulfuron, imazmethapyr or imazethapyr.
11. A herbicidal composition according to Claim 8 wherein the herbicides are dicamba and metsulfuron (-methyl).
PCT/EP1994/001669 1993-05-26 1994-05-24 Herbicidal compositions WO1994027438A1 (en)

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Cited By (5)

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EP0812540A2 (en) * 1996-06-11 1997-12-17 American Cyanamid Company Method to overcome the antagonistic interactions of herbicides
EP0963696A1 (en) * 1996-02-02 1999-12-15 Nissan Chemical Industries, Limited Herbicidal compositions
WO2000003592A2 (en) * 1998-07-16 2000-01-27 Aventis Cropscience Gnbh Herbicidal agents with substituted phenoxysulfonylureas
EP1468609A1 (en) * 1996-09-19 2004-10-20 Bayer CropScience GmbH Combinations of sulfonyl urea herbicides and safeners
US9380783B2 (en) 2012-05-08 2016-07-05 Ishihara Sangyo Kaisha, Ltd. Herbicidal composition

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0963696A1 (en) * 1996-02-02 1999-12-15 Nissan Chemical Industries, Limited Herbicidal compositions
EP0963696A4 (en) * 1996-02-02 2000-06-28 Nissan Chemical Ind Ltd Herbicidal compositions
EP0812540A2 (en) * 1996-06-11 1997-12-17 American Cyanamid Company Method to overcome the antagonistic interactions of herbicides
EP0812540A3 (en) * 1996-06-11 1998-02-11 American Cyanamid Company Method and compositions to overcome the antagonistic interactions of herbicides
EP1468609A1 (en) * 1996-09-19 2004-10-20 Bayer CropScience GmbH Combinations of sulfonyl urea herbicides and safeners
WO2000003592A2 (en) * 1998-07-16 2000-01-27 Aventis Cropscience Gnbh Herbicidal agents with substituted phenoxysulfonylureas
WO2000003592A3 (en) * 1998-07-16 2000-11-09 Aventis Cropscience Gnbh Herbicidal agents with substituted phenoxysulfonylureas
US9380783B2 (en) 2012-05-08 2016-07-05 Ishihara Sangyo Kaisha, Ltd. Herbicidal composition
US9693559B2 (en) 2012-05-08 2017-07-04 Ishihara Sangyo Kaisha, Ltd. Herbicidal composition

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