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WO1996008146A2 - Composition synergique herbicide et procede de desherbage - Google Patents

Composition synergique herbicide et procede de desherbage Download PDF

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Publication number
WO1996008146A2
WO1996008146A2 PCT/EP1995/003365 EP9503365W WO9608146A2 WO 1996008146 A2 WO1996008146 A2 WO 1996008146A2 EP 9503365 W EP9503365 W EP 9503365W WO 9608146 A2 WO9608146 A2 WO 9608146A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
composition according
herbicidal
formulae
Prior art date
Application number
PCT/EP1995/003365
Other languages
English (en)
Other versions
WO1996008146A3 (fr
Inventor
Manfred Hudetz
Urs Hofer
Original Assignee
Novartis Ag
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 Novartis Ag filed Critical Novartis Ag
Priority to AU33873/95A priority Critical patent/AU3387395A/en
Publication of WO1996008146A2 publication Critical patent/WO1996008146A2/fr
Publication of WO1996008146A3 publication Critical patent/WO1996008146A3/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<
    • A01N47/36—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 a novel herbicidal synergistic composition that contains a combination of herbicides suitable for selectively controlling weeds in crops of cultivated plants, typically in crops of rape, sugar beet, sugar cane, plantations and soybeans and, preferably, in crops of cereals, rice and maize.
  • the invention further relates to a process for controlling weeds in crops of cultivated plants and to the use of said novel composition therefor.
  • Q is the groups (Q 2 ); Qs); or
  • R is hydrogen or methyl
  • X and Y are each independently of the other methyl or methoxy; and E is nitrogen or the methine group, as disclosed in US-A-4514 212, US-A-4478 635, US-A-5 009699, EP-A-0 030 142, EP-A-0084020, EP-A-0 131 258, JP-A-60-045 573, The Agrochemicals Handbook, 2nd Edition, The Royal Society of Chemistry 1987, and Pesticide Manual, 9 th Ed. (1991), page 814, The British Crop Protection Council, London;
  • R j is chloro or trifluoromethyl; and R 2 is hydrogen or the group C 2 H 5 OCO- , as disclosed in US-A-3 652 645 and US-A-4 851 034; and
  • the present invention provides a novel synergistic composition for selectively controlling weeds, which comprises, as active ingredient, the compound of formula I
  • Q is the groups (Qj); (I ⁇ (( ); S COOCH 3
  • R is hydrogen or methyl
  • X and Y are each independently of the other methyl or methoxy; and E is nitrogen or the methine group, and/or of the compound of formula m
  • R x is chloro or trifluoromethyl; and R 2 is hydrogen or the group C 2 H 5 OCO-, and/or of the compound of formula IV
  • the rates of application of the single compounds I, II, III and IV are reduced while the effectiveness of said compounds is retained.
  • the novel herbicidal combination also achieves a high degree of weed control where the single compounds have become no longer agriculturally effective at low rates of application. The consequence is a substantial broadening of the activity spectrum against weeds and an additional increase in the selectivity for the cultivated plants that is necessary and desirable in the event of unintentional overapplication of herbicide.
  • the novel herbicidal combination can be used against a great number of agriculturally important weeds in crops of cultivated plants, including Solanum, Xanthium, Abutilon, Ambrosia, Sagittaria, Ipomoea, Cassia, Datura, Sesbania and Sida and, preferably, Veronica, Galium, Papaver, Chenopodium and Amaranthus.
  • novel compositions are suitable for all standard methods of application used in agriculture, typically preemergence application, postemergence application and seed dressing.
  • the novel herbicidal combination is preferably suitable for weed control in crops of cultivated plants, typically rape, sugar beet, sugar cane, plantations and soybean and, preferably, cereals, rice and maize.
  • Crops will be understood as meaning also those crops that have been made tolerant to herbicides or classes of herbicides by conventional breeding or genetic engineering methods.
  • the novel herbicidal combination contains the compound of formula I and one or more than one of the herbicides of formulae II to IV in any ratio, but usually with an excess of the one component over the other.
  • Preferred ratios of the compound of formula I to the components of formulae II to IV are in the range from 1:0.05 to 1:200, especially from 1:0.05 to 1:100.
  • Preferred herbicidal compositions are those comprising as active ingredient on the one hand the compound of formula I and on the other hand a synergistically effective amount of the compound of formula II.
  • herbicidal compositions are particularly preferred wherein Q is Qj to O ; E is nitrogen; X is methyl; and Y is methoxy.
  • herbicidal compositions those are very particularly preferred wherein Q is Q j or Q ; and R is hydrogen.
  • herbicidal compositions comprising as active ingredient on the one hand the compound of formula I and on the other hand a synergistically effective amount of the compound of formula IV.
  • herbicidal compositions comprising as active ingredient on the one hand the compound of formula I and on the other hand a synergistically effective amount of at least one of the compounds of formula II, III or IV.
  • the rate of application can vary over a wide range and will depend on the nature of the soil, the type of application (pre- or postemergence), seed dressing, application to the seed furrow; no tillage application etc.), the cultivated plant, the weed to be controlled, the respective prevailing climatic conditions; and on other factors governed by the type of application and the target crop.
  • the herbicidal combination can usually be applied in a rate of application of 0.01 to 2 kg/ha, preferably of 0.05 to lkg/ha.
  • the weight ratio of the component of formula I to the components of formulae II, III and/or IV in the novel formulation is from 1:200 to 1:0.05.
  • herbicidal combinations of the compound of formula I with the herbicides of formulae II, 111 and/or IV may be used in unmodified form, i.e. as obtained in the synthesis, but - 1 -
  • compositions preferably they are processed in conventional manner with the assistants customarily employed in formulation technology to directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates or microcapsules.
  • assistants customarily employed in formulation technology to directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates or microcapsules.
  • spraying, atomising, dusting, scattering or pouring are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the formulations i.e. the compositions containing the compounds of formulae I and ⁇ to IV and usually one or more than one formulation assistant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the herbicide with said formulation assistants, typically solvents or solid carriers.
  • Surface-active compounds surfactants may additionally be used for preparing the formulations.
  • Suitable solvents may typically be: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms such as mixtures of alkylbenzenes, typically xylene mixtures or alkylated naphthalenes; aliphatic and cycloaliphatic hydrocarbons such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols such as ethanol, propanol or butanol; glycols and their ethers and esters such as propylene glycol or dipropylene glycol ether; ketones such as cyclohexanone, isophorone or diacetone alcohol; strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water, vegetable oils and their esters such as rapeseed oil, castor oil or soybean oil; and in some cases also silicone oils.
  • aromatic hydrocarbons preferably the fractions containing 8 to 12 carbon atoms such as mixtures of alkylbenzen
  • the solid carriers typically used for dusts and dispersible powders are usually natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite.
  • natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite.
  • highly dispersed silicic acid or highly dispersed absorbent polymers such as calcite, talcum, kaolin, montmorillonite or attapulgite.
  • Suitable granulated adsorptive carriers are porous types, including pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are materials such as calcite or sand.
  • innumerable pregranulated materials of inorganic or organic origin may be used, especially dolomite or pulverised plant residues.
  • suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants will also be understood as comprising mixtures of surfactants.
  • Suitable anionic surfactants may be water-soluble soaps as well as water-soluble synthetic surface-active compounds.
  • Suitable soaps are the alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts of higher fatty acids (C 10 -C 22 ), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, inter alia from coconut oil or tallow oil. Further suitable soaps are also the fatty acid methyl taurin salts.
  • so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
  • the fatty alcohol sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts, and they contain a C 8 -C 22 alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of ligninsulfonic acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfated or sulfonated fatty alcohol/ethylene oxide adducts.
  • the sulfonated benz ⁇ imidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms.
  • alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a condensate of naphthalenesulfonic acid and formaldehyde.
  • Corresponding phosphates typically salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids, are also suitable.
  • Nonionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, or 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.
  • nonionic surfactants are the water-soluble polyadducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which polyadducts 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.
  • nonionic surfactants are nonylphenol polyethoxylates, polyethoxylated castor oil, polyadducts of polypropylene and polyethylene oxide, tributylphenol polyethoxylate, polyethylene glycol and octylphenol polyethoxylate.
  • Fatty acid esters of polyoxyethylene sorbitan are also suitable nonionic surfactants, typically polyoxyethylene sorbitan trioleate.
  • Cationic surfactants are preferably quaternary ammonium salts carrying, as N-substituent, at least one C 8 -C 22 alkyl radical and, as further substituents, optionally halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals.
  • the salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example stearyl trimethylammonium chloride or benzyl bis(2-chloroethyl)ethylammonium bromide.
  • the herbicidal compositions will usually contain from 0.1 to 99 % by weight, preferably from 0.1 to 95 % by weight, of a combination of the compound of formula I with the compounds of formula II to IV, from 1 to 99.9 % by weight of a solid or liquid adjuvant, and from 0 to 25 % by weight, preferably from 0.1 to 25 % by weight, of a surfactant
  • the formulations may also contain further ingredients such as stabilisers, vegetable oils or epoxidised vegetable oils, (epoxidised coconut oil, rapeseed oil or soybean oil), antifoams, typically silicone oil, preservatives, viscosity regulators, binders, tackifiers, as well as fertilisers or other chemical a «ents.
  • stabilisers vegetable oils or epoxidised vegetable oils, (epoxidised coconut oil, rapeseed oil or soybean oil), antifoams, typically silicone oil, preservatives, viscosity regulators, binders, tackifiers, as well as fertilisers or other chemical a «ents.
  • preferred formulations are made up as follows (throughout, percentages are by weight):
  • Emulsifiable concentrates herbicidal combination 1 to 90 %, preferably 5 to 20 % surfactant: 1 to 30 , preferably 10 to 20 % liquid carrier: 5 to 94 %, preferably 70 to 85 %
  • Dusts herbicidal combination: 0J to 10 %, preferably 0J to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
  • Suspension concentrates herbicidal combination: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surfactant: 1 to 40 %, preferably 2 to 30 %
  • Wettable powders herbicidal combination: 0.5 to 90 %, preferably 1 to 80 % surfactant: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 %
  • Granulates herbicidal combination: 0J to 30 %, preferably 0J to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %
  • Emulsifiable concentrates a) b) c) d)
  • Emulsions of any desired concentration can be prepared by diluting such concentrates with water.
  • the solutions are suitable for use as microdrops.
  • the compound mixture is throughly mixed with the adjuvants and this mixture is ground in a suitable mill to give wettable powders which can be diluted with water to give suspensions of any desired concentration.
  • the compound mixture is dissolved in methylene chloride, the solution is sprayed on to the carrier, and the solvent is removed under vacuum.
  • the compound mixture is mixed with the adjuvants and the mixture is moistened with water. This mixture is extruded and then dried in a stream of air.
  • Ready for use dusts are obtained by mixing the compound mixture with the carriers on a suitable mill.
  • the finely ground compound mixture is homogeneously mixed with the adjuvants to give a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.
  • a synergistic effect is always obtained when the herbicidal action of the combination of the compounds of formula I and at least one of the compounds of formulae II to IV is greater than the sum of the action of the individual herbicides.
  • Y the percentage growth, compared with untreated controls, after treatment with the compounds of formulae II to IV at a rate of application of q kg per hectare.
  • We the expected herbicidal activity (percentage growth compared with the untreated control plants) after treatment with the compounds of formulae I and ⁇ to IV at a rate of application of p + q kg per hectare. If the actually observed value is lower than the expected value We, then there is synergism.
  • test plants are raised under hothouse conditions in plastic pots to the 2-3 leaf stage.
  • the growth substrate is standard soil.
  • the herbicidal compositions are applied to the test plants singly as well as in admixture.
  • Application is made with an aqueous suspension, prepared from a 25 % wettable powder formulation (Example F3, b)) of the test substances in 5001 of water/ha with a standard spray nozzle.
  • the rates of application are determined by the optimum rates found according to field and hothouse conditions.

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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 se rapporte à une composition synergique, herbicide comprenant un composé de la formule (I), ou des sels de celui-ci, mélangé à une quantité synergiquement efficace du composé de la formule (II) dans laquelle Q représente les groupes (Q1), (Q2), (Q3), (Q4), (Q5) ou (Q6); R représente hydrogène ou méthyle, X et Y représentent chacun, indépendamment l'un de l'autre, méthyle ou méthoxy, et E représente azote ou le groupe méthine, et/ou le composé de la formule (III) dans laquelle R1 représente chloro ou trifluorométhyle; et R2 représente hydrogène ou le groupe C2H5OCD- et/ou le composé de la formule (IV) ou des sels des composés des formules (II) à (IV).
PCT/EP1995/003365 1994-09-06 1995-08-25 Composition synergique herbicide et procede de desherbage WO1996008146A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU33873/95A AU3387395A (en) 1994-09-06 1995-08-25 Herbicidal synergistic composition and method of weed conrol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272094 1994-09-06
CH2720/94-2 1994-09-06

Publications (2)

Publication Number Publication Date
WO1996008146A2 true WO1996008146A2 (fr) 1996-03-21
WO1996008146A3 WO1996008146A3 (fr) 1996-07-25

Family

ID=4240098

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/003365 WO1996008146A2 (fr) 1994-09-06 1995-08-25 Composition synergique herbicide et procede de desherbage

Country Status (2)

Country Link
AU (1) AU3387395A (fr)
WO (1) WO1996008146A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117121920A (zh) * 2023-08-28 2023-11-28 青岛瀚生生物科技股份有限公司 除草组合物及其在大豆田杂草防治中的应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE55215T1 (de) * 1986-03-07 1990-08-15 Ciba Geigy Ag Synergistisches mittel und verfahren zur selektiven unkrautbekaempfung in getreide.
MY136106A (en) * 1990-09-06 2008-08-29 Novartis Ag Synergistic composition comprising a sulfonylurea anda thiadiazolo (3,4-a)pyridazine and method of selective weed control.
ES2084975T3 (es) * 1991-01-25 1996-05-16 Ciba Geigy Ag Sulfonilureas como herbicidas.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117121920A (zh) * 2023-08-28 2023-11-28 青岛瀚生生物科技股份有限公司 除草组合物及其在大豆田杂草防治中的应用

Also Published As

Publication number Publication date
WO1996008146A3 (fr) 1996-07-25
AU3387395A (en) 1996-03-29

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