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WO2008122396A2 - Procédé d'amélioration de croissance de plante - Google Patents

Procédé d'amélioration de croissance de plante Download PDF

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Publication number
WO2008122396A2
WO2008122396A2 PCT/EP2008/002614 EP2008002614W WO2008122396A2 WO 2008122396 A2 WO2008122396 A2 WO 2008122396A2 EP 2008002614 W EP2008002614 W EP 2008002614W WO 2008122396 A2 WO2008122396 A2 WO 2008122396A2
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WO
WIPO (PCT)
Prior art keywords
methyl
cyclopropyl
plant
trifluoromethyl
formula
Prior art date
Application number
PCT/EP2008/002614
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English (en)
Other versions
WO2008122396A3 (fr
Inventor
Max Angst
Michael Schade
Christoph Vock
Ana Cristina Dutton
Original Assignee
Syngenta Participations 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 Syngenta Participations Ag filed Critical Syngenta Participations Ag
Publication of WO2008122396A2 publication Critical patent/WO2008122396A2/fr
Publication of WO2008122396A3 publication Critical patent/WO2008122396A3/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
    • 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

Definitions

  • the present invention relates to the improvement of the growth of a plant, especially increasing yield and vigor (greening enhancement, stress shield), and more particularly to a method of increasing the yield and vigor of agronomic plants by treatment of the plant or its propagation material with insecticidally active bisamide derivatives optionally in admixture with further active agents.
  • X is a bivalent group selected from
  • R 1 is hydrogen, CrC 4 alkyl or C ⁇ alkyl 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 - C 6 cycloalkyl; with the proviso that R 1 is different from unsubstituted C r C 4 alkyl if X is X 1 and R 4 is cyano;R 2 is halogen, C 1 -C 4 alkoxy, C r C 4 haloalkyl or C r C 4 haloalkoxy; R 3 is C !
  • R 4 and R 5 independently from each other, are hydrogen, d-C 4 alkyl, C 1 -C 4 BIkOXy, cyano, nitro, or halogen; and agronomically acceptable salts/isomers/enantiomers/tautomers/N- oxides of those compounds.
  • Compounds 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 d-C 4 alkanecarboxylic acids which are unsubstitu- ted 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 hydroxycarboxylic 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 CrC 4 alkane- or arylsulfonic acids which are unsubstituted or substituted, for example
  • Compounds 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 mor- pholine, 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.
  • agrochemically advantageous salts Preferred within the scope of the invention are agrochemically advantageous salts; however, the invention also encompasses salts which have disadvantage for agrochemical use, for example salts which are toxic to bees or fish, and which are employed, for example, for the isolation or purification of free compounds I or agrochemically utilizable salts thereof.
  • the free compounds I or their salts hereinabove and hereinbelow are respectively to be understood as including, where appropriate, the corresponding salts or the free compounds I.
  • the free form is preferred in each case.
  • 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. - H -
  • 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 trichloromethyl, 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 dif luorochloromethoxy, 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 present invention also relates to a novel method of improving the growth of a plant which is essentially free of insects comprising treating the plant or its propagation material with an effective amount of a compound of formula I as mentioned above.
  • Such advantageous properties are improved crop characteristics including: emergence, crop yields, protein content, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf color, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigor, and early germination; or any other advantages familiar to a person skilled in the art.
  • a good effect means at least 10% earlier emergence, crop yields, more developed root system, increase in plant height, bigger leaf blade, less fertilizers needed, less seeds needed increased shoot growth, improved plant vigor etc.
  • a further aspect of the invention is a method of using a compound of formula I in a method for Improving the growth of plants.
  • a further aspect of the invention is the use of a compound of formula I in a method for improving the growth of plants.
  • Still a further aspect of the invention is a method of using a composition comprising a compound of formula I in a method for improving the growth of plants.
  • Crops which can be improved according to the present method include cereals, such as wheat, barley, rye, oats, rice, maize and sorghum; beet, such as sugar beet and fodder beet; fruit, for example pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, e.g.
  • strawberries, raspberries and blackberries leguminous fruits, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucurbitaceae, such as marrows, cucumbersand melons; fibre plants, such as cotton, flax, hemp and jute; citrus fruit, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, such as avocados, cinnamon and camphor; and also tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas, natural rubber plants and ornamentals; especially rice, beans, soybeans, rape.
  • oil plants such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts
  • cucurbitaceae such as m
  • R 1 is cyclopropyl substituted by cyclopropyl at the 1 -position, R 2 is bromine, R 3 is methyl, R 4 is CN and X is X 1 ;
  • Ri is methyl substituted by cyclopropyl, R 2 is CF 3 , R 3 is methyl, R 4 is Cl and X is X 1 ;
  • R 1 is cyclopropyl substituted by cyclopropyl at the 1 -position, R 2 is CF 3 , R 3 is methyl, R 4 is Cl and X is X 1 ;
  • R 1 is cyclopropyl substituted by cyclopropyl at the 1 -position, R 2 is CF 3 , R 3 is methyl, R 4 is Cl and X is X 1 ;
  • R 1 is cyclopropyl substituted by cyclopropyl at the 1 -position, R 2 is CF 3 , R 3 is methyl, R 4 is CN and X is X
  • R 1 is isopropyl, R 2 is trifluoromethyl, R 3 is methyl, R 4 is methyl and X is X 3 ; m) R 1 is isopropyl, R 2 is trifluoromethyl, R 3 is Cl, R 4 is trifluoromethyl and X is X 4 ; n) R 1 is isopropyl, R 2 is trifluoromethyl, R 3 is Cl, R 4 is methoxy and X is X 5 ; and o) R 1 is isopropyl, R 2 is trifluoromethyl, R 3 is methyl and X is X 7 ; in particular from a) R 1 is cyclopropyl substituted by cyclopropyl at the 1 -position, R 2 is bromine, R 3 is methyl, R 4 is CN and X is X 1 ; b) R 1 is methyl substituted by cyclopropyl, R 2 is CF 3 , R 3 is methyl, R 4 is Cl and X
  • the compounds of formula I can be prepared analogously to known processes, for example as described, for example, in WO 04/067528, WO 2005/085234, WO 2006/111341 , WO 2007/020050 and PCT/EP2007/001283.
  • Salts of compounds I can be prepared in a manner known per se.
  • acid addition salts of compounds 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 I can be converted in the customary manner into the free compounds 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 I can be converted in a manner known per se into other salts of compounds I, 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 I which have salt- forming properties can be obtained in free form or in the form of salts.
  • the compounds 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 I, 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 microorganisms, 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 solubilities
  • 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 I according to the invention are known as 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.
  • useful plants is to be understood as including also useful plants 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®.
  • useful plants is to be understood as including also useful 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.
  • 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-acetyltransf erase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA(c) toxin); Bol
  • useful plants is to be understood as including also useful plants which have 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 1 see e.g. EP-A-O 392 225).
  • PRPs 1 see e.g. EP-A-O 392 225
  • 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.
  • locus of a useful plant as used herein is intended to embrace the place on which the useful plants are growing, where the plant propagation materials of the useful plants are sown or where the plant propagation materials of the useful plants will be placed into the soil.
  • An example for such a locus is a field, on which crop plants are growing.
  • plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably "plant propagation material” is understood to denote seeds.
  • plants which are essentially free of insects means plants in locations where the level of insect infestation is below that indicating the need for the use of an insecticide for insect control purposes.
  • the compounds of formula I can be used in unmodified form or, preferably, together with carriers and adjuvants conventionally employed in the art of formulation.
  • increasing the yield of an agronomic plant, what is meant is that the yield of a product of the plant is increased by a measurable amount over the yield of the same product of the plant produced under the same conditions, but without the application of the subject method. It is preferred that the yield be increased by at least about 0.5%, more preferred that the increase be at least about 1 %, even more preferred is about 2%, and yet more preferred is about 4%, or more.
  • the subject method is described herein as "increasing the vigor" of an agronomic plant, what is meant is that the vigor rating, or the plant weight, or the plant height, or the plant canopy, or the visual appearance, or any combination of these factors, is increased or improved by a measurable or noticeable amount over the same factor of the plant produced under the same conditions, but without the application of the subject method. It is preferred that such factor(s) is increased or improved by a significant amount.
  • the compounds of formula I can be applied in the form of pesticidal compositions such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - one of the active ingredients of formula I according to the invention and which are to be selected to suit the intended aims and the prevailing circumstances.
  • pesticidal compositions such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - one of the active ingredients of formula I according to the invention and which are to be selected to suit the intended aims and the prevailing circumstances.
  • the active ingredient is employed in pure form, a solid active ingredient for example in a specific particle size, or, preferably, together with - at least - one of the auxiliaries conventionally used in the art of formulation, such as extenders, for example solvents or solid carriers, or such as surface-active compounds (surfactants).
  • auxiliaries conventionally used in the art of formulation, such as extenders, for example solvents or solid carriers, or such as surface-active compounds (surfactants).
  • suitable solvents are: unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the fractions C 8 to C 12 of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols such as ethanol, propanol or butanol, glycols and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-me- thylpyrrolid-2-one, dimethyl sulfoxide or N.N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils, such as unexpoi
  • Solid carriers which are used for example for dusts and dispersible powders are, as a rule, ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite.
  • ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite.
  • highly disperse silicas or highly disperse absorbtive polymers are also possible to add highly disperse silicas or highly disperse absorbtive polymers.
  • Suitable particulate adsorptive carriers for granules are porous types, such as pumice, brick grit, sepiolite or bentonite, and suitable non-sorptive carrier materials are calcite or sand.
  • a large number of granulated materials of inorganic or organic nature can be used, in particular dolomite or comminuted plant residues.
  • Suitable surface-active compounds 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 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 benzylbis(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 or tall 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 atoms, alkyl also to be understood as including the alkyl moiety of acyl radicals; examples which may be mentioned are the sodium or calcium salts of lignosulfonic acid, of the dodecylsulfuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonyl groups and a fatty acid radical of approximately 8 to approximately 22 C atoms.
  • alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of decylbenzenesulfonic acid, of dibutyl- naphthalenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate.
  • suitable phosphates such as salts of the phosphoric ester of a p- nonylphenol/(4-14)ethylene oxide adduct, or phospholipids.
  • the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of active ingredient and 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid adjuvant, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, of the composition to be surfactants(% in each case meaning percent by weight).
  • the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient.
  • Emulsifiable concentrates active ingredient: 1 to 95%, preferably 5 to 20% surfactant: 1 to 30%, preferably 10 to 20 % solvent: 5 to 98%, preferably 70 to 85%
  • Dusts active ingredient: 0.1 to 10%, preferably 0.1 to 1% solid carrier: 99.9 to 90%, preferably 99.9 to 99%
  • Suspension concentrates active ingredient: 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 active ingredient: 0.5 to 90%, preferably 1 to 80% surfactant: 0.5 to 20%, preferably 1 to 15% solid carrier: 5 to 99%, preferably 15 to 98%
  • Granulates active ingredient: 0.5 to 30%, preferably 3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%
  • Example F1 Emulsion concentrates a) b) c)
  • Tributylphenoxypolyethylene glycol ether (30 mol of EO) - 12 % 4 %
  • Xylene mixture 65 % 25 % 20 % Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
  • Example F2 Solutions a) b) c) d)
  • Petroleum ether (boiling range: 160-190°) - - 94 % -
  • the solutions are suitable for use in the form of microdrops.
  • Example F3 Granules a) b) c) d)
  • the active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier(s), and the solvent is subsequently evaporated in vacuo.
  • Example F4 Dusts a) b)
  • Ready-to-use dusts are obtained by intimately mixing the carriers and the active ingredient.
  • Example F5 Wettable powders a) b) c)
  • the active ingredient is mixed with the additives and the mixture is ground thoroughly in a suitable mill. This gives wettable powders, which can be diluted with water to give suspensions of any desired concentration.
  • Example F6 Extruder granules
  • the active ingredient is mixed with the additives, and the mixture is ground, moistened with water, extruded, granulated and dried in a stream of air.
  • Example F7 Coated granules
  • the finely ground active ingredient is applied uniformLy to the kaolin, which has been moistened with the polyethylene glycol. This gives dust-free coated granules.
  • Nonylphenoxypolyethylene glycol ether (15 mol of EO) 6 %
  • Silicone oil (75 % aqueous emulsion) 0.8 %
  • 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.
  • the activity of the compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding other active ingredients.
  • 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. TomLin; The British Crop Protection Council].
  • Further preferred mixing partners for the compounds of formula I are selected from the group consisting of paclobutrazol (Chemical Abstracts Registry number 76738-62-0), acibenzolar-S-methyl (Chemical Abstracts Registry number 126448-41-7), bixafen (Chemical Abstracts Registry number 581809-46-3), fluopyram (Chemical Abstracts Registry number 658066-35-4) and the compound of formula A
  • the present invention also relates to a method of improving the growth of a plant, especially yield and vigor, comprising treating the plant or its propagation material with an effective amount of a composition comprising as active ingredients a compound of formula I as mentioned above and at least one compound selected from the class of neonicotinoid insecticides, paclobutrazol, acibenzolar-S-methyl, bixafen, fluopyram and the compound of formula A (formula A), preferably selected from the class of neonicotinoid insecticides, in particular thiamethoxam.
  • a composition comprising as active ingredients a compound of formula I as mentioned above and at least one compound selected from the class of neonicotinoid insecticides, paclobutrazol, acibenzolar-S-methyl, bixafen, fluopyram and the compound of formula A (formula A), preferably selected from the class of neonicotinoid insecticides, in particular thiamethoxam.
  • the active ingredient mixture of the compounds of formula I with the insecticides described above comprises a compound of formula I and an insecticide 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 and an 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 can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.
  • auxiliaries such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators
  • compositions according to 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).
  • 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 such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circumstances - and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention.
  • 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.
  • 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.
  • the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application).
  • compositions according to the invention are also suitable for the use in plant propagation material, for example seeds.
  • the propagation material can be treated with the compositions prior to planting, for example seed can be treated prior to sowing.
  • the compositions can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling.
  • Table B1 Vigor effect for the 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 (Compound A) and the compound of formula I, wherein R 1 is isopropyl, R 2 is trifluoromethyl, R 3 is methyl, R 4 is hydrogen and X is X 8 (Compound B);

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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)
  • Cultivation Of Plants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédé d'amélioration de croissance de plante, notamment en termes de rendement et de vigueur, qui consiste à traiter la plante ou son matériau de propagation avec une quantité efficace de composé de formule I, sachant que les substituant sont tels que définis dans la revendication 1 de l'invention.
PCT/EP2008/002614 2007-04-04 2008-04-02 Procédé d'amélioration de croissance de plante WO2008122396A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07007014 2007-04-04
EP07007014.9 2007-04-04

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WO2008122396A2 true WO2008122396A2 (fr) 2008-10-16
WO2008122396A3 WO2008122396A3 (fr) 2009-09-24

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AR (1) AR065929A1 (fr)
CL (1) CL2008000972A1 (fr)
TW (1) TW200904332A (fr)
UY (1) UY31003A1 (fr)
WO (1) WO2008122396A2 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011134876A1 (fr) 2010-04-30 2011-11-03 Syngenta Participations Ag Procédé pour réduire des infections virales provoquées par des insectes vecteurs
CN102487622A (zh) * 2011-08-29 2012-06-13 常先苗 一种控制免耕小麦弱苗的方法
CN102626107A (zh) * 2012-03-22 2012-08-08 叶长东 一种包含黄腐酸的植物生长调节剂及其用途和方法
WO2014079820A1 (fr) 2012-11-22 2014-05-30 Basf Se Utilisation de composés d'anthranilamides pour réduire les infections virales véhiculées par les insectes
RU2690884C1 (ru) * 2018-04-19 2019-06-06 Федеральное государственное бюджетное научное учреждение "Всероссийский научно-исследовательский институт биологической защиты растений" Способ повышения урожайности кукурузы
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

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10310906A1 (de) * 2003-03-13 2004-09-23 Bayer Cropscience Ag Synergistische Wirkstoffkombinationen
DE102004035134A1 (de) * 2004-07-20 2006-02-16 Bayer Cropscience Ag Selektive Insektizide auf Basis von Halogenalkylnicotinsäurederivaten, Anthranilsäureamiden oder Phthalsäurediamiden und Safenern
DE102006037120A1 (de) * 2006-03-06 2007-09-13 Bayer Cropscience Ag Synergistische Wirkstoffkombinationen

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011134876A1 (fr) 2010-04-30 2011-11-03 Syngenta Participations Ag Procédé pour réduire des infections virales provoquées par des insectes vecteurs
CN102487622A (zh) * 2011-08-29 2012-06-13 常先苗 一种控制免耕小麦弱苗的方法
CN102626107A (zh) * 2012-03-22 2012-08-08 叶长东 一种包含黄腐酸的植物生长调节剂及其用途和方法
CN102626107B (zh) * 2012-03-22 2013-12-25 叶长东 一种包含黄腐酸的植物生长调节剂及其用途和方法
WO2014079820A1 (fr) 2012-11-22 2014-05-30 Basf Se Utilisation de composés d'anthranilamides pour réduire les infections virales véhiculées par les insectes
RU2690884C1 (ru) * 2018-04-19 2019-06-06 Федеральное государственное бюджетное научное учреждение "Всероссийский научно-исследовательский институт биологической защиты растений" Способ повышения урожайности кукурузы
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

Also Published As

Publication number Publication date
WO2008122396A3 (fr) 2009-09-24
TW200904332A (en) 2009-02-01
CL2008000972A1 (es) 2008-10-10
UY31003A1 (es) 2008-11-28
AR065929A1 (es) 2009-07-08

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