WO1999052366A1 - Melanges herbicides - Google Patents

Melanges herbicides Download PDF

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Publication number
WO1999052366A1
WO1999052366A1 PCT/US1999/006042 US9906042W WO9952366A1 WO 1999052366 A1 WO1999052366 A1 WO 1999052366A1 US 9906042 W US9906042 W US 9906042W WO 9952366 A1 WO9952366 A1 WO 9952366A1
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WO
WIPO (PCT)
Prior art keywords
compound
formula
mixture
rice
control
Prior art date
Application number
PCT/US1999/006042
Other languages
English (en)
Inventor
Gene Allen Bozarth
C. Daniel Cotterman
Masashi Otani
Shinichi Shirakura
Original Assignee
E.I. Du Pont De Nemours And Company
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 E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to BR9909323-5A priority Critical patent/BR9909323A/pt
Priority to AU31031/99A priority patent/AU3103199A/en
Priority to EP99912718A priority patent/EP1073336A1/fr
Publication of WO1999052366A1 publication Critical patent/WO1999052366A1/fr

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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<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a 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 the mixture of 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5- dihydro-5-oxo-lH-tetrazole-l-carboxamide (Formula I)
  • This invention also relates to a herbicidal composition comprising herbicidally effective amounts of the aforesaid mixture 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 mixture.
  • the preferred application of the mixture 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 No. 5,362,704. The synthesis involves the coupling of the tetrazolinone of Formula 1 with the carbamyl chloride of Formula 2.
  • the Formula II compound can be prepared as described in German Patent 1,039,779.
  • the synthesis involves coupling of the aniline of Formula 3 with the activated acyl group of Formula 4.
  • LG is a leaving group such as halogen Formulation
  • 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
  • the mixture 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 (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredients.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
  • 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 ⁇ V-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 ⁇ V-dimethylformamide, dimethyl sulfoxide, JV-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.
  • 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. Patent No. 3,060,084.
  • Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp ⁇ 41-4%, Perry 's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546.
  • Pellets can be prepared as described in U.S. Patent No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Patent Nos. 4,144,050 and 3,920,442 and DE Patent No. 3,246,493. Tablets can be prepared as taught in U.S. Patent Nos. 5,180,587; 5,232,701; and 5,208,030. Films can be prepared as taught in GB Patent No. 2,095,558 and U.S. Patent No. 3,299,566.
  • the mixture 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 mixture of the invention is 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 this mixture provides in controlling bamyardgrass without injury to rice is both very valuable and remarkable, as both bamyardgrass and rice are grasses.
  • Bamyardgrass is one of the most troublesome weeds in rice fields.
  • weeds are killed or sufficiently injured to provide the rice crop a competitive advantage.
  • Application to direct seeded rice at the preemergence to 5-leaf stage, application to transplanted rice at the 1.0-5.0-leaf stage and application to weeds at the preemergence to 4-leaf stage is preferable.
  • Herbicidally effective amounts of the compounds of Formula I and Formula II will vary depending on environmental conditions, formulation, method of application, amount and type of vegetation present, etc.
  • the use rate weight ratios of Formula I to Formula II are typically 1 :2 to 1:100, with ratios of 1 :5 to 1 :40 preferred for most uses.
  • the Formula I compound is applied at a rate from 100 to 400 g ai/ha and the Formula II compound is applied at a rate from 1000 to 6000 g ai ha.
  • the Formula I compound is applied at a rate from 200 to 300 g ai/ha
  • the Formula II compound is applied at a rate from 2000 to 4000 g ai/ha.
  • 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, indanofan, pretilachlor, oxaziclomefone, thiobencarb, pyributicarb, pyrazolate, benxofenap, bromobutid, mefenacet, anilofos and benfuresate.
  • Particularly useful herbicide mixture partners are the sulfonylurea herbicides azimsulfuron, bensulfuron methyl, metsulfiiron 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. 7
  • Compound 1 is the Formula I compound 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo- lH-tetrazole- 1 -carboxamide and Compound 2 is the Formula II compound propanil.
  • ba yardgrass Echinochloa crus-galH
  • ba yardgrass Echinochloa crus-galH
  • a Tama silt loam soil was used for the propagation.
  • Rice Oryza sativa, cv. IR64
  • Compounds 1 and 2 were formulated in a non-phytotoxic solvent mixture and applied to the leaf surfaces as a foliar spray. The soil surface was flooded to a 3 cm depth 48 hours after the plants were treated.
  • Treated plants and untreated controls were maintained under greenhouse conditions for 14 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- 22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form:
  • Pa+b Pa + Pb - (P a Pb 100) wherein P a +b is the percentage effect of the mixture expected from additive contribution of the individual components,
  • P a is the observed percentage effect of the first active ingredient at the same use rate as in the mixture
  • Pb 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. TABLE A*

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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

L'invention concerne un mélange herbicide comprenant du 4-(2-chlorophényl) -Ncyclohexyl- N-éthyl-4, 5-dihydro-5 -oxo-1H-tétrazole-1- carboxamide et du N-(3, 4-dichlorophényl) propanamide(propanil), des compositions herbicides dudit mélange, ainsi qu'un procédé d'utilisation de ce mélange permettant de lutter contre toute végétation indésirable.
PCT/US1999/006042 1998-04-15 1999-03-19 Melanges herbicides WO1999052366A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BR9909323-5A BR9909323A (pt) 1999-03-19 1999-03-19 Mistura herbicida, composição agricolamente aceitável e método para controlar o crescimento de vegetação indesejada.
AU31031/99A AU3103199A (en) 1998-04-15 1999-03-19 Herbicidal mixtures
EP99912718A EP1073336A1 (fr) 1998-04-15 1999-03-19 Melanges herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US8177198P 1998-04-15 1998-04-15
US60/081,771 1998-04-15

Publications (1)

Publication Number Publication Date
WO1999052366A1 true WO1999052366A1 (fr) 1999-10-21

Family

ID=22166283

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/006042 WO1999052366A1 (fr) 1998-04-15 1999-03-19 Melanges herbicides

Country Status (4)

Country Link
EP (1) EP1073336A1 (fr)
CN (1) CN1296381A (fr)
AU (1) AU3103199A (fr)
WO (1) WO1999052366A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014043153A1 (fr) * 2012-09-13 2014-03-20 Dow Agrosciences Llc Compositions herbicides comprenant de l'aminopyralide et du propanil

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3540919A1 (de) * 1985-11-19 1987-05-21 Bayer Ag Herbizide mittel enthaltend photosynthesehemmer-herbizide in kombination mit cyclischen harnstoffderivaten
EP0612735A1 (fr) * 1993-02-25 1994-08-31 Nihon Bayer Agrochem K.K. Dérivés de 1-(phényle substituée)-tetrazolinone, leur préparation et leur utilisation comme herbicides
DE19801637A1 (de) * 1997-01-21 1998-07-23 Bayer Ag Selektive Herbizide auf Basis von 1-(2-Chlor-phenyl)-4-(N-cyclohexyl-N-ethyl-aminocarbonyl)-1,4-dihydro-5H-tetrazol-5-on und Propanil

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3540919A1 (de) * 1985-11-19 1987-05-21 Bayer Ag Herbizide mittel enthaltend photosynthesehemmer-herbizide in kombination mit cyclischen harnstoffderivaten
EP0612735A1 (fr) * 1993-02-25 1994-08-31 Nihon Bayer Agrochem K.K. Dérivés de 1-(phényle substituée)-tetrazolinone, leur préparation et leur utilisation comme herbicides
DE19801637A1 (de) * 1997-01-21 1998-07-23 Bayer Ag Selektive Herbizide auf Basis von 1-(2-Chlor-phenyl)-4-(N-cyclohexyl-N-ethyl-aminocarbonyl)-1,4-dihydro-5H-tetrazol-5-on und Propanil

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014043153A1 (fr) * 2012-09-13 2014-03-20 Dow Agrosciences Llc Compositions herbicides comprenant de l'aminopyralide et du propanil
EP2894988A4 (fr) * 2012-09-13 2016-06-08 Dow Agrosciences Llc Compositions herbicides comprenant de l'aminopyralide et du propanil

Also Published As

Publication number Publication date
AU3103199A (en) 1999-11-01
EP1073336A1 (fr) 2001-02-07
CN1296381A (zh) 2001-05-23

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