WO2009021717A2 - Formulation pesticide - Google Patents

Formulation pesticide Download PDF

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Publication number
WO2009021717A2
WO2009021717A2 PCT/EP2008/006631 EP2008006631W WO2009021717A2 WO 2009021717 A2 WO2009021717 A2 WO 2009021717A2 EP 2008006631 W EP2008006631 W EP 2008006631W WO 2009021717 A2 WO2009021717 A2 WO 2009021717A2
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methyl
spp
ccn
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name
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WO2009021717A3 (fr
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Johanna Martina Williams
Ana Christina Dutton
Julia Lynne Ramsay
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Syngenta Participations AG
Syngenta Ltd
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Syngenta Participations AG
Syngenta Ltd
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    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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

Definitions

  • the present invention relates to novel insecticidal active compositions, in particular to insecticidal active composition comprising a bisamide derivative, and an adjuvant component and to their use for controlling insects or representatives of the order Acarina.
  • formulation types are used in the agrochemical industry. The choice of formulation type depends on various factors, including the physical properties of the active ingredient itself. Oil dispersions are particularly useful for formulations containing oil insoluble active ingredients. It is further known from US-A-4,834,908 that certain crop oil concentrates are useful to increase the herbicidal activity of diverse chemical classes and assist in defeating the apparent antagonism which arises in herbicidal mixtures.
  • WO 2007/081553 describes suspension concentrate comp ⁇ siiio ⁇ s of carboxamide arthropodicides which can contain water-immiscible carrier selected from a fatty acid ester of a CrC 4 alkanol, a vegetable oil and a mineral oil. Liquid formulations and tensid/solvent systems which comprise completely esterified organic phosphates and/or phosphonates as solvents are described in EP1164842B1.
  • Bisamide derivatives with insecticidal activity are known and described, for example, in WO 04/067528, WO 2005/085234, WO 2006/111341 , WO07/020050, WO06/040113, and WO 2007/093402.
  • the object of the present invention is thus a pesticidal composition
  • X is a bivalent group
  • R 1 is C 3 -C 6 cycloalkyl substituted by C 3 -C 6 cycloalkyl
  • R 2 is halogen, Crdalkoxy, CrC ⁇ aloalkyl or C 1 -C 4 haloalkoxy;
  • R 3 is C 1 -C 4 alkyl or halogen
  • R 4 is hydrogen, Ci-C 4 alkyl, C 1 -C 4 BIkOXy, cyano, nitro, or halogen; or X is a bivalent group selected from
  • R 1 is hydrogen, C 1 -C 4 SlKyI or C 1 -C 4 SlKyI substituted with one or two groups selected from C 3 -C 6 cycloalkyl and cyano; or R 1 is C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by C 3 -
  • R 2 is halogen, CrC 4 alkoxy, C ! -C 4 haloalkyl or d-C 4 haloalkoxy;
  • R 3 is CrC 4 alkyl or halogen
  • R 4 and R 5 independently from each other, are hydrogen, C r C 4 alkyl, CrC 4 alkoxy, cyano, nitro, or halogen; and agronomically acceptable salts/isomers/enantiomers/tautomers/N- oxides of those compounds and b) at least one adjuvant component selected from b1) an oil additive comprising an oil of vegetable or animal origin, a mineral oil, the alkylesters thereof or mixtures of these oils and oil derivatives; b2) an adjuvant having the formula (II)
  • the compounds of formula I which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrose acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as CrC 4 alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxy ⁇ c acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as C r C 4 alkane- or arylsulfonic acids which are unsubstituted or substituted, for example
  • Compounds of formula I which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower- alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine.
  • the corresponding internal salts can furthermore be formed.
  • alkyl groups occurring in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
  • Halogen is generally fluorine, chlorine, bromine or iodine.
  • Haloalkyl groups preferably have a chain length of from 1 to 6 carbon atoms.
  • Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1 ,1-difluoro- 2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloro- methyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.
  • Haloalkoxy groups preferably have a chain length of from 1 to 6 carbon atoms.
  • Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloromethoxy, 2,2,2- trifluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2-chloroethoxy, pentafluoroethoxy, 2,2,3,3-tetrafluoroethoxy and 2,2,2-trichloroethoxy; preferably difluorochloromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy and 2,2,2- trifluoroethoxy.
  • Alkoxy groups preferably have a preferred chain length of from 1 to 6 carbon atoms.
  • Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy; preferably methoxy and ethoxy.
  • the cycloalkyl groups have from 3 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • the compounds of formula I, wherein X is X 1 , X 2 , X 3 or X 8 are preferred.
  • the compounds of formula I, wherein X is X 8 are especially preferred for the use in the compositions according to the present invention.
  • compositions according to the present invention are selected from the compounds of formula I described in Table 1 :
  • the compounds of formula I can be prepared analogously to known processes, for example as described, for example, in WO 2005/085234,WO 2006/111341 , WO 2007/020050 , WO2006/040113, and WO2007/093402.
  • Salts of compounds of formula I can be prepared in a manner known per se.
  • acid addition salts of compounds of formula I are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.
  • Salts of compounds of formula I can be converted in the customary manner into the free compounds of formula I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.
  • Salts of compounds of formula I can be converted in a manner known per se into other salts of compounds of formula I 1 acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.
  • a salt of inorganic acid such as hydrochloride
  • a suitable metal salt such as a sodium, barium or silver salt
  • the compounds of formula I 1 which have salt-forming properties can be obtained in free form or in the form of salts.
  • the compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can be present in the form of one of the isomers which are possible or as a mixture of these, for example in the form of pure isomers, such as antipodes and/or diastereomers, or as isomer mixtures, such as enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms which occur in the molecule and/or depending on the configuration of non-aromatic double bonds which occur in the molecule; the invention relates to the pure isomers and also to all isomer mixtures which are possible and is to be understood in each case in this sense hereinabove and hereinbelow, even when stereochemical details are not mentioned specifically in each case.
  • Diastereomer mixtures or racemate mixtures of compounds of formula I 1 in free form or in salt form which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diasteromers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography.
  • Enantiomer mixtures such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high- performance liquid chromatography (HPLC) on acetyl celulose, with the aid of suitable mi- croorganisms, by cleavage with specific, immobilized enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer is com- plexed, or by conversion into diastereomeric salts, for example by reacting a basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphor, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid, and separating the diastereomer mixture which can be obtained in this manner, for example by fractional crystallization based on their differing so
  • Pure diastereomers or enantiomers can be obtained not only by separating suitable isomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials of a suitable stereochemistry.
  • the compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
  • Preferred adjuvant components b) are adjuvants known as penetrations enhancers and/or spreaders and wetters and combinations thereof.
  • Pentetration enhancers are adjuvants which increase the amount of a pesticide that is taken up in the plant and/or decreases the time span for the agrochemical to be taken up.
  • Spreading and wetting adjuvants are additives which increase the sprayed area by increasing the spread for the spray droplet on the leafs.
  • Preferred adjuvant components b) are adjuvant components b1) which are oil based and contain mineral oils also known as liquid petrolatum, paraffin oil, paraffinic oil, comprise a mixture of long-chain, liquid hydrocarbons obtained from petroleum, or oils of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives like methylated rape seed oil, or an oil of animal origin, such as fish oil or beef tallow and mixtures thereof.
  • mineral oils also known as liquid petrolatum, paraffin oil, paraffinic oil
  • mineral oils of vegetable origin for example rapeseed oil, olive oil or sunflower oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives like methylated rape seed oil, or an oil of animal origin, such as fish oil or beef tallow and mixtures thereof.
  • Further preferred adjuvant components b1) contain alkylesters or alkylethers of higher fatty acids and alcohols (C 8 -C 22 ), especially the methyl and ethyl derivatives of C 12 -Ci 8 fatty acids, for example the methylesters of lauric acid, palmitic acid and oleic acid. These esters are known as methyl laurate (CAS-111-82-0), methyl palmitate (CAS-112-39-0) and methyl oleate (CAS-112-62-9).
  • the hydrocarbon chain can be branched or unbranched, saturated or unsaturated or OH substituted.
  • These alkylated esters and ethers can also include polyethoxylated or polypropoxylated esters and a mixture thereof.
  • Particularly preferred polyethoxylated fatty alcohols contain 8 - 20 ethoxylates, for example oleic acid ethoxylate with EO up to 20. (Genopol® 0100, Genopol® 0120)
  • Further preferred adjuvant components b) contain sorbitan fatty esters and ethoxylated sorbitan fatty esters, (particularly Tween® 80 and Tween® 85).
  • Further preferred adjuvant components b) are the components b3) which are based on phosphate or phopsphonate chemistry.
  • Especially preferred phosphate or phopsphonate components are selected from the group consisting of c1) esters of phosphoric acid with alcohols selected from the group consisting of monohydric alkanols having 5 to 22 carbon atoms, diols or polyols, aryl, alkylaryl, poly(alkyl)aryl or poly (arylalkyl)aryl alcohols, alkoxylated alcohols obtained by reacting the above mentioned alcohols with alkylene oxides, and alkoxylated alcohols obtained by reacting monohydric alkanols with 1 to 4 carbon atoms and alkylene oxides, and c2) phosphonates based on alkyl-, aryl-, alkylaryl-, poly(alkyl)aryl- or poly(arylalkyl)arylphonsphonic acids diesterified with alcohols and/or
  • phosphate or phopsphonate components and its preparation is described in EP 1164842B1.
  • An especially preferred surface active component b) of this class is tris-(2- ethylhexyl)phosphate.
  • Further preferred adjuvant components b) are the components b2) which are based on butyl endcapped ethoxylated fatty acids of formula Il as described in EP 1427280A0.
  • R 6 in formula Il is an alkenyl group it may have one or more double bonds which may be in either cis or trans configuration(s).
  • R 6 has from 1 to 3 double bonds. It is generally preferred that the double bond(s) are in the cis configuration.
  • R 6 is a C 18 branched chain alkyl or Ci 8 alkenyl group for example oleyl or isostearyl (derived from the alcohol, 2-hexyl-dodecan-1-ol).
  • n is preferably from 10 to 30 and especially from 10 to 20.
  • the value of n may be an integer when a specific and uniform number of groups R 2 O are introduced or may be an average value when a range of numbers of such groups are introduced.
  • the value of m is preferably 0.
  • R 8 is not hydrogen it is preferably a Ci to C 4 alkyl group and in particular methyl or butyl. Butyl is especially preferred. Those skilled in the art will appreciate that an alkyl group R 8 represents an "end cap" to the terminal hydroxy! of the group
  • R 7 is ethyl
  • R 8 is not hydrogen when R 7 is ethyl.
  • R 8 may be hydrogen or alkyl since both moieties achieve the objects of the invention. It is thus possible to "end cap” only a proportion of the terminal hydroxyl groups such that R 8 is a mixture of hydrogen and alkyl groups.
  • oleyl 10 propylene oxide i.e. a compound of formula Il wherein R 6 is oleyl, m is 0, R 7 is isopropylene, n is 10 and R 8 is hydrogen
  • oleyl 10 propylene oxide end-capped butyl ether i.e.
  • R 6 is oleyl, m is 0, R 7 is isopropylene, n is 10 and R 8 is butyl
  • oleyl 20 propylene oxide isoleyl 20 propylene oxide end-capped butyl ether, isostearyl 10 propylene oxide, isostearyl 20 propylene oxide, oleyl 10 ethylene oxide end-capped butyl ether, oleyl 20 ethylene oxide end-capped butyl ether, oleic acid 10 ethylene oxide end-capped methyl ether (i.e.
  • compositions according to the present invention comprises as oil additives mineral oil, sunflower oil or methylated rape seed oil.
  • oils additives suitable for the compositions according to the present invention which comprise mixtures of oils or mineral oils, or the derivatives thereof, with surfactants, are Edenor ME SU®, Emery 2231®, Turbocharge® (Zeneca Agro, Stoney Creek, Ontario , CA), AGRIDEX® (Bayer AG) or Actipron® (BP Oil UK Limited, GB).
  • the application and efficacy of the oil additives can be improved by combining them with surface-active substances, such as non-ionic, anionic or cationic surfactants.
  • surface-active substances such as non-ionic, anionic or cationic surfactants.
  • suitable anionic, non-ionic, and cationic surfactants are listed in WO 97/34485 on pages 7 and 8.
  • Suitable surface-active substances are, depending on the type of the active ingredient to be formulated, non-ionic, cationic and/or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties.
  • the surfactants mentioned below are only to be considered as examples; a large number of further surfactants which are conventionally used in the art of formulation and suitable according to the invention are described in the relevant literature.
  • Suitable non-ionic surfactants are, especially, polyglycol ether derivatives of aliphatic or cyc- loaliphatic alcohols, of saturated or unsaturated fatty acids or of alkyl phenols which may contain approximately 3 to approximately 30 glycol ether groups and approximately 8 to approximately 20 carbon atoms in the (cyclo)aliphatic hydrocarbon radical or approximately 6 to approximately 18 carbon atoms in the alkyl moiety of the alkyl phenols.
  • water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopo- lypropylene glycol or alkyl polypropylene glycol having 1 to approximately 10 carbon atoms in the alkyl chain and approximately 20 to approximately 250 ethylene glycol ether groups and approximately 10 to approximately 100 propylene glycol ether groups.
  • the abovementioned compounds contain 1 to approximately 5 ethylene glycol units per propylene glycol unit.
  • nonylphenoxypolyethoxyethanol examples which may be mentioned are nonylphenoxypolyethoxyethanol, castor oil polyglycol ether, polypropylene glycol/polyethylene oxide adducts, tributylpheno- xypolyethoxyethanol, polyethylene glycol or octylphenoxypolyethoxyethanol.
  • fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate.
  • the cationic surfactants are, especially, quarternary ammonium salts which generally have at least one alkyl radical of approximately 8 to approximately 22 C atoms as substituents and as further substituents (unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzyl radicals
  • the salts are preferably in the form of halides, methylsulfates or ethylsulfates Examples are stearyltrimethylammonium chloride and benzylb ⁇ s(2-chloroethyl)ethyl- ammonium bromide
  • Suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surface-active compounds
  • suitable soaps are the alkali, alkaline earth or (un- substituted or substituted) ammonium salts of fatty acids having approximately 10 to approximately 22 C atoms, such as the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which are obtainable for example from coconut nr t.aii oil, mention must also be made of the fatty acid methyl taurates
  • synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates
  • the fatty sulfonates and fatty sulfates are present as alkali, alkaline earth or (substituted or unsubstituted) ammonium salts and they generally have an alkyl radical of approximately 8 to approximately 22 C
  • Preferred surface-active substances are anionic surfactants of the dodecylbenzene sulfonate type, especially the calcium salts thereof, as well as non-ionic surfactants of the fatty alcohol ethoxylate type Especially preferred are ethoxylated C 12 -C 22 -fatty alcohols with a degree of ethoxylation of between 5 and 40 Examples of commercially available, preferred surfactants are the Genapol types (Clariant AG, Muttenz, Switzerland) The concentration of surface-active substances in relation to the total additive is in general between 1 and 30% by weight.
  • an organic solvent to the oil additive/surfactant mixture can effect a further increase in efficacy.
  • Suitable solvents are for example the Solvesso® (ESSO) or Aromatic Solvent® (Exxon Corporation) types.
  • the concentration of such solvents may be from 10 to 80% by weight of the total weight.
  • compositions comprising oil additives of this kind, which are also described for example in US-A-4,834,908, are a further embodiment of the present invention.
  • a preferred oil additive is known under the name MERGE® which can be obtained from the BASF Corporation and is basically described for example in US-A-4,834,908 in column 5, as example COC-1.
  • a further preferred oil additive according to the invention is SCORE® (Novariis Crop Protection Canada) and Adigor.
  • Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient.
  • the rate of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha.
  • the adjuvant is applied to so that the ratio of the adjuvant to the active ingredient lies in between 1 :1 and 10000:1 , preferably in between 10:1 and 5000:1.
  • the formulations which are used to obtain the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • compositions that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circum- stances - and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention.
  • a preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question.
  • compositions according to the present invention can be preferably formulated as emulsion concentrates, suspension concentrates, oil dispersions, suspoemulsions, wettable powders or wettable granules, suspension concentrates are especially preferred.
  • the adjuvant b) is added to a suspension concentrate which contains the compounds of formula I.
  • the adjuvant b) can either be build into the formulation concentrate which comprises the active or tank-mixed.
  • Emulsion Concentrates :
  • Active ingredient 1-50 %, preferably 1-20%
  • Surfactants 1-30 %, preferably 5-25%
  • Solvent 2-98 %, preferably 50-95%
  • Active ingredient 5-65 %, preferably 10-50%
  • Surfactants 1-30%, preferably 2-25%
  • the finely ground active ingredient is mixed intimately with the additives.
  • Suspensions of any desired concentration can be prepared from the thus resulting suspension concentrate by dilution with water.
  • Active ingredient 5-65 %, , preferably 10-50%
  • Surfactants 1-30 %, preferably 2-25%
  • Oil 2-98 %, preferably 50-95%
  • Active ingredient 0.5-80 % , preferably 1-70%
  • Surfactants 0.5-30%, preferably 2-25%
  • Carrier material 1-98%, preferably 50-90%
  • Active ingredient 0.5-80 %, preferably 1-70%
  • Surfactants 0.5-30%, preferably 2-25%
  • Carrier material 1-98%, preferably 50-90%
  • Examples of preferred adjuvant components b) according to the present invention are:
  • Oils a. Mineral oils: SUNSPRAY®, CROPSPRAY® (Sun Oil company, Belgium), Isopar® V (Exxon), paraffin oils, TURBOCHARGE® (Zeneca Agro, Stoney Creek, Ontario , CA), MERGE® (BASF) or Adigor®.
  • Vegetable oils oils obtained from plants, (especially sunflower, olive, soja, castor oil) and seed oils.
  • Emulsogen® M (Clariant) Tween® 80, Tween® 85
  • An example for a suitable blend is: Ethoxylated Oleyl-polyglycolether (10 EO) 5% Ethoxylated Oleyl-polyglycolether (12 EO) 15%
  • compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding other insecticidally, acaricidally and/or fungicidally active ingredients.
  • mixtures of the compounds of formula I with other insecticidally, acaricidally and/or fungicidally active ingredients may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity. For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled in their different development stages or better behaviour during their production, for example during grinding or mixing, during their storage or during their use.
  • Suitable additions to active ingredients are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridyl- methyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.
  • TX means "one compound selected from the group consisting of the compounds of formula I described in Table 1 of the present invention"
  • doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothion (1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, ethoate-methyl (1134) + TX, etoxazole (320) + TX, etrimfos (1142) + TX, fenazaflor (1147) + TX, fenazaquin (328) + TX, fenbutatin oxide (330) + TX, fenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, fenson (1157) + TX, fentrifanil (1161) + TX, fenvalerate (349
  • butathinfos (927) + TX, butccarboxirn (103) + TX, butonate (932) + TX, butoxycarboxim (104) + TX 1 butylpyridaben (alternative name) + TX, cadusafos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (1 15) + TX, carbofuran (118) + TX, carbon disulfide (lUPAC/Chemical Abstracts name) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbophenothion (947) + TX 1 carbosulfan (119) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, vertex (
  • Ra 5 is trifluoromethyl or difluoromethyl (WO2004/058723) + TX, the compound of formula F-2
  • Ra 6 is trifluoromethyl or difluoromethyl (WO2004/058723) + TX, the racemic compound of formula F-3 (syn)
  • Ra 9 is trifluoromethyl or difluoromethyl (WO03/074491) + TX, the compound of formula F-9
  • R 10 is trifluoromethyl or difluoromethyl (WO2004/058723) + TX, the racemic compound of formula F-11 (trans)
  • Rn is trifluoromethyl or difluoromethyl (WO03/074491) + TX, the racemic compound of formula F-12 (cis)
  • the active ingredient mixture of the compounds of formula I selected from Table 1 with active ingredients described above comprises a compound selected from Table 1 and an active ingredient as described above preferably in a mixing ratio of from 100:1 to 1 :6000, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1 :1 , or 5:1, or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 1 :35
  • the mixtures comprising a compound of formula I selected from Table 1 and one or more active ingredients as described above can be applied, for example, in a single "ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the compounds of formula I selected from Table 1 and the active ingredients as described above is not essential for working the present invention.
  • compositions according to the present invention as additional insecticidal active ingredients compounds selected from the class of neonicotinoid insecticides.
  • Preferred compounds from the class of neonicotinoid insecticides are thiamethoxam (792) (available commercially as HELIX® and CRUISER®), imidacloprid (458) (available commercially as GAUCHO®) clothianidine (165), thiacloprid (791), dinotefuran (271), nitenpyram (579) and acetamiprid (4).
  • Said compounds are described under the entry number given in round brackets hereinabove in the "The Pesticide Manual” [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S.
  • the present invention also relates to a method of controlling pests comprising treating the plant or its propagation material with an effective amount of a composition comprising as active ingredients a) a compound of formula I as mentioned above; b) at least one adjuvant component selected from b1) an oil additive comprising an oil of vegetable or animal origin, a mineral oil, the alkylesters thereof or mixtures of these oils and oil derivatives; b2) an adjuvant having the formula (II)
  • R 6 is a Ci 6 to C 2 o straight or branched chain alkyl or alkenyl group
  • R 7 is ethyl or isopropyl
  • n is from 8 to 30
  • m is 0 or 1 and when R 7 is ethyl, R 8 is a C 1 to C 7 alkyl group and when R 7 is isopropyl, R 8 is hydrogen or a C 1 to C 7 alkyl group
  • b3 one or more completely esterified organic phosphates and/or phosphonates, or mixtures of said surface active compounents
  • at least one compound selected from the class of neonicotinoid insecticides at least one compound selected from the class of neonicotinoid insecticides.
  • the active ingredient mixture of the compounds of formula I with neonicotinoid insecticides described above comprises a compound of formula I and an neonicotinoid insecticide 3 ⁇ described above preferably in a mixing ratio of from 100:1 to 1 :6000, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300,
  • the mixtures comprising a compound of formula I and an neonicotinoid insecticide as described above can be applied, for example, in a single "ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the compounds of formula I and the neonicotinoid insecticides as described above is not essential for working the present invention.
  • compositions according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants.
  • the active ingredients according to the invention act against all or individual developmental stages of normally sensitive, but also resistant, animal pests, such as insects or representatives of the order Acarina.
  • the insecticidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly, i. e.
  • Examples of the abovementioned animal pests are: from the order Acarina, for example,
  • Haematopinus spp. Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; from the order Coleoptera, for example,
  • Curculio spp. Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Leptinotarsa decemLineata, Lissorhoptrus spp., Melolontha spp., Orycaephilus spp., Otiorhynchus spp.,
  • Aedes spp. Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp.,
  • Tabanus spp., Tannia spp. and Tipula spp. from the order Heteroptera, for example, Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp., Eurygaster spp., Lep- tocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotino- phara spp. and Triatoma spp.; from the order Homoptera, for example,
  • Aleurothrixus floccosus Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, Aphis spp., Aspi- diotus spp., Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus hesperidum, Empoasca spp., Eriosoma larigerum, Erythroneura spp.,
  • Myzus spp. Nephotettix spp., Nilaparvata spp., Parlatoria spp., Pemphigus spp., Planococ- cus spp., Pseudaulacaspis spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica,
  • Quadraspidiotus spp. Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri; from the order Hymenoptera, for example,
  • Vespa spp. from the order Isoptera, for example,
  • Reticulitermes spp. from the order Lepidoptera, for example,
  • Ostrinia nubilalis Pammene spp., Pandemis spp., Panolis flammea, Pectinophora gossypi- ela, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scir- pophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Synanthedon spp.,
  • Thaumetopoea spp. Tortrix spp., Trichoplusia ni and Yponomeuta spp.; from the order Mallophaga, for example,
  • Blatta spp. Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. and Schistocerca spp.; from the order Psocoptera, for example,
  • Liposcelis spp. from the order Siphonaptera, for example,
  • compositions according to the invention can be used for controlling, i. e. containing or destroying, pests of the abovementioned type which occur in particular on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage or stalks of such plants.
  • Suitable target crops are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous crops, such as beans, lentils, peas or soya; oil crops, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts,
  • compositions according to the invention are especially suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and Spodoptera littoralis in cotton, vegetable, maize, rice and soya crops.
  • the compositions according to the invention are further especially suitable for controlling Mamestra (preferably in vegetables), Cydia pomonella (preferably in apples), Empoasca(preferably in vegetables, vineyards), Leptinotarsa (preferably in potatos) and Chilo supressalis (preferably in rice).
  • crops is to be understood as including also crops that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • ALS inhibitors for example primisulfuron, prosulfuron and trifloxysulfuron
  • EPSPS 5-enol-pyrovyl-shikimate-3-phosphate-synthase
  • GS glutamine synthetase
  • imazamox by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®.
  • crops is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example insecticidal proteins from Bacillus cereus or Bacillus popliae; or insecticidal proteins from Bacillus thuringiensis, such as ⁇ -endotoxins, e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi) or Cry9c, or vegetative insecticidal proteins (VIP), e.g. VIP1 , VIP2, VIP3 or VIP3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp.
  • insecticidal proteins for example insecticidal proteins from Bacillus cereus or Bacillus popliae
  • Bacillus thuringiensis such as ⁇ -endotoxins, e.g. CrylA(b), CrylA(c), CrylF, CrylF(a
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsine inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecd
  • ⁇ -endotoxins for example CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi) or Cry9c, or vegetative insecticidal proteins (VIP), for example VIP1 , VIP2, VIP3 or VIP3A
  • VIP1 , VIP2, VIP3 or VIP3A expressly also hybrid toxins, truncated toxins and modified toxins.
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701).
  • Truncated toxins for example a truncated CrylA(b), are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • amino acid replacements preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of CrylllA055, a cathepsin-D-recognition sequence is inserted into a CrylllA toxin (see WO 03/018810).
  • Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-O 374 753, WO 93/07278, WO 95/34656, EP-A-O 427 529, EP-A-451 878 and WO 03/052073.
  • Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-O 367 474, EP-A-O 401 979 and WO 90/13651.
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CrylllB(bi) toxin); YieldGard Plus® (maize variety that expresses a CrylA(b) and a CrylllB(bi) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CrylF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA(c) toxin);
  • crops is to be understood ss including also crop piants whicn nave been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-O 392 225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-O 392 225, WO 95/33818 and EP-A-O 353 191.
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called "pathogenesis-related proteins" (PRPs; see e.g. EP-A- 0 392 225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g. WO 95/33818) or protein or polypeptide factors involved in plant pathogen defence (so-called "plant disease resistance genes", as described in WO 03/000906).
  • ion channel blockers such as blockers for sodium and calcium channels
  • the viral KP1 , KP4 or KP6 toxins for example the viral KP1 , KP4 or KP6 toxins
  • stilbene synthases such as the viral K
  • Example B1 Translaminar test method (Activity against Aphis craccivora)
  • Bush bean plants Paneolus vulgaris var. Autan
  • Plants were treated with compounds and the following day aphids were placed on the lower leaf side.
  • Aphis craccivora were placed within a glue ring to prevent them from moving from the lower leaf side.
  • Bush beans were kept in the growth chamber at a temperature of 20 ⁇ 1 °C, 50-65% relaltive humidity, and 16 hours light.
  • the application rates are 100, 50 and 25 ppm active substance.
  • Assessment was conducted 7 days after application. Number of live aphids was counted and then converted to % mortality. Mortalities corrected using Abbott's formula. The results are given in Table B1.
  • Example B2 Feeding contact test method (Aphis craccivora on broad beans and Myzus persicae on pea seedlings). Rates 25, 12.5, 6 ppm active substance Insects: Myzus persicae (mix population)
  • Aphis craccivora mixed population Plants: Pea seedlings - Pisum sativum few day old emerging seedlings
  • Pea seedlings or Bush beans were infested with A. craccivora or M. persicae respectively. Plants were treated with samples. Plants were kept in the growth chamber at a temperature of 20 ⁇ 1 °C, 50-65% relaltive humidity, and 16 hours light.
  • the active ingredients of formula I are formulated as suspension concentrates (SC).
  • SC suspension concentrates
  • the adjuvant b) is then tank-mixed with the SC formulations.
  • Soprophor 3D33 is a tristyril-phenol-phosphates-polyethoxylated with 17 Ethoxylates made by Rhodia).
  • Atlox 4913 is polymethyl methacrylate-polyethylene glycol graft copolymer.
  • the following adjuvants b) are used: mineral oil sunflower oil
  • ADIGOR® (contains 48.8% methylated rape seed oil and 28.2 % ethoxylated alcohols), manufactured by Syngenta Crop Protection Canada, Inc..
  • CET Speed (contains 4.9% oleyl-polyglycolether with ethylene oxide (non-ionic surfactant) in form of GENAPOL® O-100, 14.7% oleyl-ppolyglycolether with ethylene oxide (non-ionic surfactant) in form of GENAPOL® 0-120, 14.7% DL-propanediol(1 ,2) in form of 1 ,2- propylene glycol and rest water).
  • Oil 1 mineral oil
  • Oil 2 sunflower oil
  • Table B1 insecticidal action in % mortality of a compound of formula I, wherein R 1 is isopropyl, R 2 is methoxy; R 3 is methyl, R 4 is hydrogen and X is X 8 ; against Aphis craccivora:
  • Table B2 insecticidal action in % mortality of a compound of formula I 1 wherein R 1 is isopropyl, R 2 is methoxy; R 3 is methyl, R 4 is hydrogen and X is X 8 ; against Aphis craccivora:
  • Table B3 insecticidal action in % mortality of a compound of formula I, wherein R 1 is isopropyl, R 2 is methoxy; R 3 is methyl, R 4 is hydrogen and X is X 8 ; against Aphis craccivora:

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Abstract

La présente invention porte sur de nouvelles compositions actives insecticides comprenant un dérivé de bisamide à activité insecticide, représenté par la formule (I), les substituants étant définis dans la revendication 1, et b) au moins un composant adjuvant choisi parmi b1) un additif d'huile comprenant une huile d'origine végétale ou animale, une huile minérale, les esters alkyliques de celles-ci ou des mélanges de ces huiles et des dérivés d'huile ; b2) un adjuvant ayant la formule (II) R6-(CO)m-O-[-R7O-]n-R8, R6 étant un groupe alkyle ou alcényle à chaîne droite ou ramifiée en C16 à C20, R7 étant un groupe éthyle ou isopropyle, n valant de 8 à 30 et m valant 0 ou 1. Lorsque R7 représente un groupe éthyle, R8 est un groupe alkyle en C1 à C7 et lorsque R7 représente un groupe isopropyle, R8 est un atome d'hydrogène ou un groupe alkyle en C1 à C7 ; et b3) un ou plusieurs phosphates et/phosphonates organiques complètement estérifiés, ou des mélanges desdits composants adjuvants.
PCT/EP2008/006631 2007-08-14 2008-08-12 Formulation pesticide Ceased WO2009021717A2 (fr)

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Cited By (7)

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KR101344765B1 (ko) 2011-12-27 2013-12-24 한국화학연구원 4,5-디히드로옥사졸-2-일벤젠 유도체의 제조방법
EP3150068A1 (fr) * 2007-08-16 2017-04-05 Basf Se Composition et procédé de traitement de semences
JP2021508688A (ja) * 2017-12-20 2021-03-11 ピーアイ インダストリーズ リミテッドＰｉ Ｉｎｄｕｓｔｒｉｅｓ Ｌｔｄ ピラゾロピリジン−ジアミド、殺虫剤としてのそれらの使用およびそれらの製造方法
JP2022550573A (ja) * 2019-10-03 2022-12-02 エフ エム シー コーポレーション ジアミド殺虫剤組成物
WO2023006634A1 (fr) * 2021-07-27 2023-02-02 Syngenta Crop Protection Ag Procédé de lutte contre des nuisibles résistants au diamide et composés associés
WO2023021020A1 (fr) * 2021-08-19 2023-02-23 Syngenta Crop Protection Ag Procédé de lutte contre des nuisibles résistants au diamide et composés associés
WO2025132148A1 (fr) 2023-12-21 2025-06-26 Bayer Aktiengesellschaft Compositions d'adjuvant pour applications agrochimiques

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VN23181A1 (en) * 2003-01-28 2010-07-26 Du Pont Cyano anthranilamide insecticides
AR048669A1 (es) * 2004-03-03 2006-05-17 Syngenta Ltd Derivados biciclicos de bisamida
GB0422556D0 (en) * 2004-10-11 2004-11-10 Syngenta Participations Ag Novel insecticides
BRPI0610542B1 (pt) * 2005-04-20 2014-10-14 Syngenta Participations Ag Inseticidas de antranilamida de ciano, composição pesticida e método para o controle de pestes
GB0516703D0 (en) * 2005-08-15 2005-09-21 Syngenta Participations Ag Novel insecticides
TWI324908B (en) * 2006-01-05 2010-05-21 Du Pont Liquid formulations of carboxamide arthropodicides
US8658801B2 (en) * 2006-02-16 2014-02-25 Syngenta Crop Protection, Llc Pesticides containing a bicyclic bisamide structure

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3150068A1 (fr) * 2007-08-16 2017-04-05 Basf Se Composition et procédé de traitement de semences
KR101344765B1 (ko) 2011-12-27 2013-12-24 한국화학연구원 4,5-디히드로옥사졸-2-일벤젠 유도체의 제조방법
JP2021508688A (ja) * 2017-12-20 2021-03-11 ピーアイ インダストリーズ リミテッドＰｉ Ｉｎｄｕｓｔｒｉｅｓ Ｌｔｄ ピラゾロピリジン−ジアミド、殺虫剤としてのそれらの使用およびそれらの製造方法
JP2022550573A (ja) * 2019-10-03 2022-12-02 エフ エム シー コーポレーション ジアミド殺虫剤組成物
US20240057602A1 (en) * 2019-10-03 2024-02-22 Fmc Corporation Diamide insecticide compositions
JP7717688B2 (ja) 2019-10-03 2025-08-04 エフ エム シー コーポレーション ジアミド殺虫剤組成物
WO2023006634A1 (fr) * 2021-07-27 2023-02-02 Syngenta Crop Protection Ag Procédé de lutte contre des nuisibles résistants au diamide et composés associés
WO2023021020A1 (fr) * 2021-08-19 2023-02-23 Syngenta Crop Protection Ag Procédé de lutte contre des nuisibles résistants au diamide et composés associés
WO2025132148A1 (fr) 2023-12-21 2025-06-26 Bayer Aktiengesellschaft Compositions d'adjuvant pour applications agrochimiques

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