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WO1998058545A1 - Melanges herbicides - Google Patents

Melanges herbicides Download PDF

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Publication number
WO1998058545A1
WO1998058545A1 PCT/US1998/012585 US9812585W WO9858545A1 WO 1998058545 A1 WO1998058545 A1 WO 1998058545A1 US 9812585 W US9812585 W US 9812585W WO 9858545 A1 WO9858545 A1 WO 9858545A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
herbicidal mixture
methylphenoxy
chloro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1998/012585
Other languages
English (en)
Inventor
Gene Allen Bozarth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of WO1998058545A1 publication Critical patent/WO1998058545A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to mixtures of herbicides that have a synergistic effect on weeds.
  • This invention relates to mixtures of N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]- carbonyl]-l-methyl-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazole-5-sulfonamide (azimsulfuron, Formula I)
  • W is O or S
  • R is H or C r C 14 alkyl; or an agriculturally suitable salt thereof, which have now been discovered to synergistically control weeds.
  • This invention also relates to herbicidal compositions comprising herbicidally effective amounts of the aforesaid mixtures and at least one of the following: surfactant, solid or liquid diluent.
  • This invention also relates to a method of controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the aforesaid mixtures.
  • the compound of Formula II can be in the form of an agriculturally suitable salt when R is H.
  • Agriculturally suitable salts of the compound of Formula I and the compound of Formula II (where R is H) include salts of the alkali metals, such as lithium, sodium and potassium, ammonium and ammonium mono-, di-, tri- or tetrasubstituted with C j -Ci4 alkyl or benzyl, and trialkylsulfonium and trialkylsulfoxonium, where the alkyl groups are independently selected from -C3 alkyl.
  • Preferred herbicidal compositions comprise effective amounts of said preferred herbicidal mixtures and at least one of the following: surfactant, solid or liquid diluent.
  • Preferred methods of controlling undesired vegetation comprises applying to the locus of the vegetation herbicidially effective amounts of the preferred mixtures or compositions thereof.
  • the preferred application of the mixtures of this invention is in rice crops, especially in paddy rice cultivation.
  • the Formula I compound can be prepared as described in U.S. Patent 4,746,353.
  • the synthesis involves the coupling of the pyrazolesulfonamide of Formula 1 with the heterocyclic carbamate of Formula 2.
  • the mixtures of the present invention can include the sulfonylurea compound of
  • Formula I as one or more of its agriculturally suitable salts.
  • metal salts can be made by contacting the sulfonylurea of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride).
  • Quaternary amine salts can be made by similar techniques.
  • Salts of the sulfonylurea of Formula I can also be prepared by exchange of one cation for another.
  • Cationic exchange can be effected by direct contact of an aqueous solution of a salt of the sulfonylurea of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.
  • Exchange may also be effected by passing an aqueous solution of a salt of a sulfonylurea of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation-exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column.
  • a salt of a sulfonylurea of Formula I e.g., an alkali metal or quaternary amine salt
  • a cation-exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column.
  • Formula II comprises MCPA and its agriculturally suitable esters and salts. These have long been known and used as herbicides (see The Pesticide Manual, Tenth Edition, Crop Protection Publications, United Kingdom, 1994, pp. 638-642). They are interconvertable by a wide variety of esterification, saponification and salt forming methodologies known in the art. MCPA and its derivatives are available from many commercial sources.
  • the Formula I and Formula II compounds can be formulated separately and applied separately or applied simultaneously in an appropriate weight ratio, e.g., as a tank mix; or (b) the Formula I and Formula II compounds can be formulated together in the proper weight ratio.
  • Mixtures of the Formula I and Formula II compounds will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent and/or a surfactant wherein the formulation is consistent with the physical properties of the active ingredients, mode of application and environmental factors such as soil type, moisture and temperature.
  • Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels.
  • Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble. Active ingredients can be
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene . sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
  • Solutions can be prepared by simply mixing the ingredients.
  • Chemically stabilized aqueous sulfonylurea or agriculturally suitable sulfonylurea salt dispersions are taught in U.S. 4,936,900.
  • Solution formulations of sulfonylureas with improved chemical stability are taught in U.S. 4,599,412.
  • Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S.
  • Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning,
  • Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S.
  • Example A High Strength Concentrate azimsulfuron 0.5% (4-chloro-2-methylphenoxy)acetic acid, dimethylamine salt 98.0% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
  • Example B Wettable Powder azimsulfuron 16.2%
  • Mixtures of the herbicidal compounds of Formula I and Formula II are now discovered to provide unexpected synergistic control of selected weeds while retaining selective safety to certain annual monocot plant species such as rice.
  • the mixtures of the invention are effective in selectively controlling the growth of undesirable upland and aquatic grass, broadleaf, and sedge weed species while having little or no effect upon transplanted or direct seeded japonica or indica rice.
  • the synergism these mixtures provide in controlling barnyardgrass without injury to rice is both very valuable and remarkable, as both barnyardgrass and rice are grasses.
  • weeds are killed or sufficiently injured to provide the rice crop a competitive advantage.
  • Application to direct seeded or transplanted rice at the 3 -leaf to panicle initiation stage, and application to weeds at the preemergence to tillering stage is preferable.
  • Application can be made to intermittently, continuous flood or upland rice culture.
  • Herbicidally effective amounts of the compounds of Formula I (azimsulfuron) and Formula II (MCPA and agriculturally suitable derivatives) will vary depending on environmental conditions, formulation, method of application, amount and type of vegetation present, etc.
  • the use rate ratios of Formula I to Formula II are in general 1 :3 to 1 :200, with ratios of 1 :8 to 1 :40 preferred for most uses.
  • the Formula I compound is applied at a rate from 5 to 30 g ai/ha and the Formula II compound is applied at a rate from 100 to 1000 g ai/ha.
  • the Formula I compound is applied at a rate from 10 to 25 g ai/ha
  • the Formula II compound is applied at a rate from 100 to 400 g ai/ha.
  • One skilled in the art can readily determine application rates and ratios of the herbicide of Formula I to the herbicide of Formula II as well as timing necessary for the desired level of weed control and crop safety.
  • the mixtures of the invention may be employed in further admixture with other known herbicides and agricultural crop protection chemicals to provide additional spectrum of activity against additional weed species.
  • Herbicides which may be mixed include, but are not limited to, cyhalofop-butyl, cafenstrole, dimepiperate, epoprodan, etobenzanid, pretilachlor, thenylchlor, thiobencarb, pyributicarb, pyrazolate, benxofenap, bromobutid, mefenacet, anilofos and benfuresate.
  • Particularly useful herbicide mixture partners are the sulfonylurea herbicides bensulfuron methyl, metsulfuron methyl, chlorimuron ethyl, pyrazosulfuron ethyl, imazosulfuron, cinosulfuron and cyclosulfamuron.
  • mixtures of the invention may be combined with agriculturally acceptable additives such as surfactants, safeners, spreaders, emulsifiers or fertilizers, to improve performance.
  • agriculturally acceptable additives such as surfactants, safeners, spreaders, emulsifiers or fertilizers, to improve performance.
  • the mixtures of the invention will generally be used as formulated compositions.
  • Compound 1 is the Formula I compound azimsulfuron and Compound 2 is the Formula II compound 4-chloro-2-methyphenoxy)acetic acid in the form of its dimethylamine salt, commonly referred to as MCPA- dimethylammonium.
  • Treated plants and untreated controls were maintained under greenhouse conditions for 16 days at which time treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table A, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control.
  • Colby's equation was used to calculate the expected additive herbicidal effect of the mixtures of Compound 1 with Compound 2.
  • Colby's equation (Colby, S. R. "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations," Weeds, 15(1), pp 20-
  • P a is the observed percentage effect of the first active ingredient at the same use rate as in the mixture
  • Pt ⁇ is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.
  • Combinations of Compound 1 with Compound 2 are surprisingly found to provide better control of certain weeds than expected by calculation from Colby's equation, thus demonstrating synergism.
  • Table A lists visual assessments of control of a specific weed with Compound 1 and Compound 2 applied alone as single active ingredients, applied as a mixture of the two active ingredients of Compound 1 and Compound 2, and the expected additive effect of the herbicidal mixture of Compound 1 and Compound 2 (Colby's equation).
  • Different ratios of Compound 1 to Compound 2 and different formulation types also provide useful weed control from the combination of the two herbicides.

Landscapes

  • 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

L'invention concerne des mélanges herbicides comprenant de l'azimsulfuron et du MCPA, des compositions herbicides comprenant lesdits mélanges et une méthode d'utilisation desdits mélanges pour lutter contre la végétation indésirable.
PCT/US1998/012585 1997-06-20 1998-06-16 Melanges herbicides Ceased WO1998058545A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US5037597P 1997-06-20 1997-06-20
US60/050,375 1997-06-20

Publications (1)

Publication Number Publication Date
WO1998058545A1 true WO1998058545A1 (fr) 1998-12-30

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ID=21964895

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/012585 Ceased WO1998058545A1 (fr) 1997-06-20 1998-06-16 Melanges herbicides

Country Status (1)

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WO (1) WO1998058545A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014002110A1 (fr) * 2012-06-26 2014-01-03 Rallis India Limited Composés de pyrazole substitués et leur procédé de préparation

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5612284A (en) * 1993-05-26 1997-03-18 Sandoz Ltd. Herbicidal compositions comprising a growth regulating herbicide to safen sulfonylurea herbicides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5612284A (en) * 1993-05-26 1997-03-18 Sandoz Ltd. Herbicidal compositions comprising a growth regulating herbicide to safen sulfonylurea herbicides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014002110A1 (fr) * 2012-06-26 2014-01-03 Rallis India Limited Composés de pyrazole substitués et leur procédé de préparation

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