WO2009153539A2 - Procédés de lutte contre les insectes résistants aux néonicotinoïdes - Google Patents

Procédés de lutte contre les insectes résistants aux néonicotinoïdes Download PDF

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Publication number
WO2009153539A2
WO2009153539A2 PCT/GB2009/001401 GB2009001401W WO2009153539A2 WO 2009153539 A2 WO2009153539 A2 WO 2009153539A2 GB 2009001401 W GB2009001401 W GB 2009001401W WO 2009153539 A2 WO2009153539 A2 WO 2009153539A2
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WIPO (PCT)
Prior art keywords
insects
neonicotinoid
active ingredient
resistant
dihydro
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PCT/GB2009/001401
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English (en)
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WO2009153539A3 (fr
Inventor
Robert John Lind
Robert Senn
Russell Slater
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Syngenta Limited
Syngenta Participations Ag
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Priority to JP2011514108A priority Critical patent/JP2011524886A/ja
Priority to CN2009801275831A priority patent/CN102098920A/zh
Priority to KR1020117001121A priority patent/KR20110018948A/ko
Publication of WO2009153539A2 publication Critical patent/WO2009153539A2/fr
Publication of WO2009153539A3 publication Critical patent/WO2009153539A3/fr

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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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines

Definitions

  • the invention relates to a method of controlling insects that are resistant to neo- nicotinoid insecticides, using compounds of formula I
  • compositions comprising said compounds to control neonicotinoid resistant insects relate to controlling neonicotinoid resistant insects in the Delphacidae and Cicadellidae families, especially planthoppers (e.g. insects of the genus Nilapan/ata, Sogatella and/or Laodelphax), and/or leafhoppers that are resistant to one or more neonicotinoid insecticides.
  • planthoppers e.g. insects of the genus Nilapan/ata, Sogatella and/or Laodelphax
  • leafhoppers e.g. insects of the genus Nilapan/ata, Sogatella and/or Laodelphax
  • leafhoppers e.g. insects of the genus Nilapan/ata, Sogatella and/or Laodelphax
  • leafhoppers e.g. insects of the genus Nilapan/ata, Sogatella and/or Laodelphax
  • leafhoppers e.g. insects of the
  • the neonicotinoids represent the fastest-growing class of insecticides introduced to the market since the commercialization of pyrethroids (Nauen & Denholm, 2005: Archives of Insect Biochemistry and Physiology 58:200-215) and are extremely valuable insect control agents not least because they had exhibited little or no cross-resistance to the older insecticide classes, which suffer markedly from resistance problems.
  • reports of insect resistance to the neonicotinoid class of insecticides are on the increase, with confirmed reports of resistance in aphids, whitelfy and Colorado Potato (Nauen & Denholm, supra).
  • Planthoppers insects from the Delphacidae family
  • leafhoppers insects from the Cicadellidae family
  • Planthoppers including Nilaparvata lugens (brown planthopper; BPH), Laodelphax st ⁇ atellus (small brown planthopper) and Sogatella furcifera (white-backed planthopper) are major pests of rice in many parts of Asia and cause damage in several ways.
  • R 1 is hydrogen, C 1 -Ci 2 alkyl, C 3 - C 6 cycloalkyl, C 1 -C 4 alkoxy-C r C 6 alkyl, halo-C r C 2 alkyl, phenyl, benzyl, phenethyl, phenylpropyl, phenylbutyl or phenylpentyl, or a phenyl, benzyl, phenethyl, phenylpropyl, phenylbutyl or phenylpentyl radical mono- or all-substituted by halogen, C 1 -C 5 alkyl, ha!o-C 1 -C 2 alkyl, methoxy and/or by ethoxy, and R 2 is hydrogen, C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl, or phenyl that is unsubstituted or
  • US 5,646,124 describes the use of pymetrozine for controlling specific insects within the Order Hemiptera, namely insects from the Aleyrodidae, Cicadellidae and Delphacidae families.
  • the present invention is based on the finding that pymetrozine can be successfully used to control neonicotinoid resistant populations of the brown planthopper. This is particularly surprising as it is known that cross-resistance between neonicotinoid and pymetrozine insecticides occurs in other insects including the tobacco whitefly (Bemisia tabaci) (Aguilar-Medel et al. 2007 lnterciencia 32(4):266-269; Wyss et al. 2001 Poster "Pymetrozine - new Whitefly Product in Spain” presented at European Whitefly Symposium held in Ragusa, Italy, 27 th Feb-3 rd March).
  • a method of controlling insects from the Cicadellidae and Delphacidae families which are resistant to a neonicotinoid insecticide comprises applying the active ingredient 4,5- dihydro-6 ⁇ methyl-4-(3-pyridylmethyIeneamino)-1 ,2,4-triazin-3(2H)-one in free form or in agrochemically acceptable salt form to said neonicotinoid resistant insects.
  • the invention also provides a method of protecting a crop of useful plants, wherein said crop is susceptible to and/or under attack from such insects.
  • Such a method involves applying 4,5-dihydro-6-methyl-4-(3-pyridylmethyleneamino)-1 ,2,4-triazin-3(2/V)-one in free form or in agrochemically acceptable salt form to said crop and/or said insects. Since the active ingredient 4,5-dihydro-6-methyl-4-(3-pyridylmethyleneamino)-
  • 1 ,2,4-triazin-3(2/-/)-one does not exhibit cross-resistance to neonicotinoid resistant planthoppers, it may be used in a resistance management strategy with a view to controlling resistance to the neonicotinoid class of insecticides.
  • a resistance management strategy may involve alternating applications of 4,5-dihydro-6-methyl-4-(3-pyridylmethyleneamino)- 1 ,2,4-triazin-3(2H)-one and a neonicotinoid insecticide, either on an application by application alternation, or seasonal/crop alternation basis (e.g. use pymetrozine on a first crop/for control in a first growing season, and use a neonicotinoid insecticide for a subsequent crop/growing season, or wee versa), and this forms yet a further aspect of the invention.
  • a further aspect of the invention provides a method of controlling a plant virus in a crop of useful plants susceptible to and/or under attack by neonicotinoid resistant insects which carry said plant virus, which method comprises applying to said crop and/or said insects the active ingredient 4,5-dihydro-6- methyl-4-(3-pyridy)methyleneamino)-1 ,2,4-triazin-3(2H)-one in free form or in agrochemica ⁇ y acceptable salt form.
  • plant viruses that may be controlled according to this aspect of the invention include ragged stunt oryzavirus, grassy stunt tenuivirus, and rice stripe virus.
  • Methods of the invention as described herein may also involve a step of assessing whether insects are resistant to neonicotinoid insecticides and/or whether said insects carry a plant virus.
  • This step will in general involve collecting a sample of insects from the area (e.g. crop, field, habitat) to be treated, before actually applying 4,5- dihydro-6-methyl-4-(3-pyridylmethyleneamino)-1,2,4-triazin-3(2/-/)-one, and testing (for example using any suitable phenotypic, biochemical or molecular biological technique applicable) for resistance/sensitivity and/or the presence or absence of a virus.
  • neonicotinoid insecticide refers to any insecticidal compound that acts at the insect nicotinic acetylcholine receptor, and in particular refers to those compounds classified as neonicotinoid insectides according to Yamamoto (1996, Agrochem Jpn 68:14-15).
  • Examples of neonicotinoid insecticides include those in Group 4A of the IRAC (insecticide resistance action committee, Crop Life) mode of action classification scheme, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam, as well as any compound having the same mode of action.
  • control or “controlling” as applied to insects, it is meant that the targeted insects are repelled from or less attracted to the crops to be protected.
  • control may also refer to the inability, or reduced ability, of the insects to feed or lay eggs. These terms may further include that the targeted insects are killed.
  • the method of the invention may involve the use of an amount of the active ingredient that is sufficient to repel insects (i.e a repellently effective amount of active ingredient), an amount of the active ingredient that is sufficient to stop insects feeding, or it may involve the use of an insectiddally effective amount of active ingredient (i.e. an amount sufficient to kill insects), or any combination of the above effects.
  • control or “controlling” are applied to viruses it is meant that the level of viral infection of a crop of useful plants is lower than would be observed in the absence of any application of 4,5-dihydro-6-methyl-4-(3-pyridylmethylene-amino)-1 ,2,4-triazin- 3(2H)-one.
  • applying and “application” are understood to mean direct application to the insect to be controlled, as well as indirect application to said insect, for example through application to the crop or plant on which the insect acts as pest, or to the locus of said crop or insect.
  • 4,5-dihydro-6-methyl-4-(3-pyridylmethylene-amino)-1 ,2,4-triazin-3(2H)-one may be applied by any of the known means of applying pesticidal compounds.
  • the pests or to a locus of the pests such as a habitat of the pests, or a growing plant liable to infestation by the pests
  • any part of the plant including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.
  • a locus of the pests such as a habitat of the pests, or a growing plant liable to infestation by the pests
  • any part of the plant including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots,
  • the methods of the invention are particularly applicable to the control of neonicotinoid resistant planthopper or leafhopper insects, i.e. insects from the Delphacida ⁇ and/or Cicadellidae families. More specifically, pymetrozine may be used according to the invention to control neonicotinoid resistant insects (and neonicotinoid resistance in insects) of the genera Laodelphax, Nilaparvata, and/or Sogatella, and in particular Nilaparvata l ⁇ gens, Laodelphax stratellus and/or Sogatella furcifera.
  • the methods of the invention have the effect of controlling insect pest and or viral infestation in crops of useful plants, said methods may also be viewed as methods of improving and/or maintaining plant health in said crops or as methods of increasing/maintaining the well-being of a crop.
  • Crops of useful plants that may be protected according to the invention, and to which 4,5-dihydro-6-methyl-4-(3-pyridylmethyleneamino)-1 ,2,4-thazin-3(2H)-one may be applied in accordance with the invention, include cereal crops, for example, crops of wheat, barley, rye, oats, rice, maize; fruit crops, for example, pomes, stone fruit and soft fruit (in particular apples, pears, plums, peaches, almonds, cherries, and berries); crops of leguminous plants, for example.
  • the crops of useful plants are cereal crops, and in particular crops of rice.
  • Crops of useful plants are to be understood as including those which are/have been made tolerant to herbicides or classes of herbicide (such as, for example, imidazolinones such as imazamox, as is the case with Clearfield® Rice) and/or insecticide or classes of insecticide, and/or which have acquired a so-called "output" trait (e.g. improved storage stability, higher nutritional value, improved yield etc.) by conventional plant-breeding or genetic engineering methods.
  • herbicides or classes of herbicide such as, for example, imidazolinones such as imazamox, as is the case with Clearfield® Rice
  • insecticide or classes of insecticide e.g. improved storage stability, higher nutritional value, improved yield etc.
  • useful plants include those where the plants are transgenic, or where the plants have inherited a trait as a consequence of the introduction at least one transgene in their lineage.
  • 3(2H)-one and its agrochemicaliy acceptable salts may be made, for example, as described in EP 0314615. Alternatively, it may be obtained commercially as a formulated composition, for example under the trade marks FULFILL®, CHESS®, and PLENUM®.
  • Agrochemicaliy acceptable salts of the compounds of formula I are, for example, acid addition salts.
  • salts are formed, for example, with strong inorganic acids, such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halogen-substituted, C 1 -C 4 alkanecarboxylic acids, for example formic acid, acetic acid or trifluoroacetic acid, unsaturated or saturated dicarboxylic acids, for example oxalic, malonic, succinic, maleic, fumaric or phthalic acid, hydroxycarboxylic acids, for example ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulfonic adds, such as unsubstituted or substituted, for example halogen-substituted, C 1 -C 4 alkane- or aryl-sulfonic acids, for example
  • any reference to the free compounds of formula I or their agrochemicaliy acceptable salts is to be understood as including also the corresponding agrochemicaliy acceptable salts or the free compounds of formula I, - respectively, where appropriate and expedient.
  • the methods of the invention employ the free form of 4,5-dihydro-6-methyl-4-(3-pyridylmethylene amino)-1 ,2,4-triazin-3(2H)-one .
  • the compound of formula I in free form or in agrochemically acceptable salt form may be in the form of tautomers.
  • any reference to the compound of formula I in free form or in agrochemically acceptable salt form is also, where appropriate, to be understood as including corresponding tautomers, even when the latter are not specifically mentioned in every case.
  • the compound of formula I (as well as all isomers and/or tautomers thereof) in free form, may also be in the form of any one of the solvates or hydrates as described in International Patent Publication Number WO 00/68222.
  • dihydrate form of 4,5-dihydro-6-methyl-4-(3-pyridylmethyleneamino)-1 ,2,4-triazin-3(2H)-one is preferred for use in the invention.
  • an active ingredient in particular neonicotinoid resistant insects
  • said active ingredient may be used in pure form or, more typically, formulated into a composition which includes, in addition to said active ingredient, a suitable inert diluent or carrier and optionally, a surface active agent (SFA).
  • SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting).
  • SFAs include non-ionic, cationic and/or anionic surfactants, as well as surfactant mixtures.
  • the active ingredient will be in the form of a composition additionally comprising a agriculturally acceptable carrier or diluent.
  • the composition is generally used in methods of the invention such that the active ingredient is applied at a concentration are from 0.1 to 1000 ppm, preferably from 0.1 to 500 ppm, of active ingredient.
  • spray mixtures with active ingredient concentrations of 50, 100, 200, 300 or 500 ppm are used.
  • the rates of application per hectare are generally from 1 to 2000 g of active ingredient per hectare, especially from 10 to 1000 g/ha, preferably from 20 to 600 g/ha, more preferably from 12.5 to 300 g/ha. Rates of application of 50, 100, 150, 200, 250, 300, or 400 g of active ingredient per hectare are preferred.
  • compositions can be chosen from a number of formulation types, including d ⁇ stable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations.
  • DP d ⁇ stable powders
  • SP soluble powders
  • SG water soluble granules
  • WP water dispersible granules
  • GR granules
  • SL soluble concentrates
  • OL oil miscible liquid
  • Dustable powders may be prepared by mixing the active ingredient with one ormore solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
  • solid diluents for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers
  • Soluble powders may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
  • water-soluble inorganic salts such as sodium bicarbonate, sodium carbonate or magnesium sulfate
  • water-soluble organic solids such as a polysaccharide
  • WP Wettable powders
  • WG Water dispersible granules
  • Granules may be formed either by granulating a mixture of the active ingredient and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing the active ingredient (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing the active ingredient (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary.
  • a porous granular material such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs
  • a hard core material such as sands, silicates, mineral carbonates, sulfates
  • Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils).
  • solvents such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters
  • sticking agents such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils.
  • One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
  • DC Dispersible Concentrates
  • DC may be prepared by dissolving the active ingredient in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallisation in a spray tank).
  • Emulsifiable concentrates or oil-in-water emulsions (EW) may be prepared by dissolving the active ingredient in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents).
  • Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N- octylpyrrolidone), dimethyl amides of fatty acids (such as C 8 -C 10 fatty acid dimethylamide) and chlorinated hydrocarbons.
  • aromatic hydrocarbons such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark
  • ketones such as
  • An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment.
  • Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion.
  • Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.
  • Microemulsions may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation.
  • the active ingredient is present initially in either the water or the solvent/SFA blend.
  • Suitable solvents for use in MEs include those hereinbefore described for use in ECs or in EWs.
  • a ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation.
  • a ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.
  • SC Suspension concentrates
  • SCs may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles the active ingredient.
  • SCs may be prepared by ball or bead milling the solid active ingredient in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound.
  • One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle.
  • the active ingredient may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
  • Aerosol formulations comprise the active ingredient and a suitable propellant (for example n-butane). Active ingredients may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps.
  • a suitable propellant for example n-butane
  • Active ingredients may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps.
  • the active ingredient may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
  • Capsule suspensions may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerisation stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains the active ingredient and, optionally, a carrier or diluent therefor.
  • the polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure.
  • the compositions may provide for controlled release of the compound of the active ingredient. Active ingredients may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
  • a composition may include one or more additives to improve the -biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of the active ingredient.
  • additives include surface active agents, spray additives based on oils, for example certain mineral oils, natural plant oils (such as soy bean and rape seed oil) and/or modified plant oils (e.g. esterified plant oils), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of the active ingredient.
  • compositions for use in methods of the invention are composed in particular of the following constituents (throughout, percentages are by weight):
  • Emulsifiable concentrates active ingredient: 1 to 90%, preferably 5 to 20% SFA: 1 to 30%, preferably 10 to 20% solvent: 5 to 98%, preferably 70 to 85%
  • SC Suspension concentrates
  • WP Wettable powders
  • Granules (GR, SG, WG): active ingredient: 0.5 to 60%, preferably 5 to 60%, more preferably 50 to 60% solid carrier/diluent: 99.5 to 40%, preferably 95 to 40%, more preferably 50 to 40%
  • composition will be a DP, GR, WG or WP formulation, more preferably it will be a WG or WP formulation (e.g. CHESS® WG,
  • Pymetrozine may be applied to a neonicotinoid resistant insect or crop of useful plants using any standard application method with which the skilled man is familiar.
  • neonicotinoid insecticides may be applied to an insect/crop of useful plants using any known method of application.
  • Example F1 Solutions a) b) c) d) active ingredient 80% 10% 5% 95% ethylene glycol monomethyl ether 20% - polyethylene glycol (mol. wt 400) - 70%
  • N-methyl-2-pyrrolidone 20% epoxidised coconut oil - - 1% 5% petroleum fraction (boiling range 160-1 ⁇ O.degree.) - - 94%
  • Example F2 Granules a) b) c) d) ⁇ active ingredient 5% 10% 8% 21%
  • the active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier, and the solvent is subsequently evaporated off in vacuo.
  • Example F3 Dusts a) b) active ingredient 2% 5%
  • Ready-for-use dusts are obtained by intimately mixing the carriers with the active ingredient.
  • Example F4 Wettable powders active ingredient 25% Sodium sulphate 5% castor oil polyethylene glycol ether (36-37 mol of ethylene oxide) 10% silicone oil 1 %
  • the active ingredient is mixed with the other formulation components and the mixture is ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of the desired concentration.
  • Example F5 Dusts a) b) active ingredient 5% 8%
  • Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill.
  • Example F6 Extruder granules active ingredient 10%
  • the active ingredient is mixed and ground with the other formulation components, and the mixture is subsequently moistened with water.
  • the moist mixture is extruded and granulated and then the granules are dried in a stream of air.
  • Example F7 Coated granules active ingredient 3%
  • Kaolin 94% The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
  • Example F8 Suspension concentrate active ingredient 40%
  • the finely ground active ingredient is intimately mixed with the other formulation components giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.
  • Example F9 Emulsifiable concentrates a) b) c) active ingredient 25% 40% 50%
  • Tristyrylphenol polyethylene glycol ether (30 mol of - 12% 4% ethylene oxide
  • Emulsions of any desired concentration can be produced from such concentrates by dilution with water.
  • Example F10 Wettable powders a) b) c) active ingredient 25% " 50% 75%
  • the active ingredient is mixed with the other formulation components and the mixture is ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of the desired concentration.
  • Example F11 Emulsifiable concentrate active ingredient 10%
  • Emulsions of any required concentration can be obtained from this concentrate by dilution with water.
  • Rice seedlings were planted in a 9cm diameter plastic container and grown using soil as planting medium. 8 weeks after sowing the soil, the top sections of all the rice seedlings were removed by cutting them with scissors, to leave shoots which were 25cm in length. The soil in each pot was then covered with molten agar, which was then ' allowed to set.
  • test pots were placed in holding racks and covered with plastic vapour tubes, before being infested with 10 anaesthetised BPH nymphs (L5 life stage, 20 days after hatching).
  • the test containers were then incubated at 25°C with a 16-hour photoperiod.
  • BPH nymph/adult mortality was assessed 7 days after infestation. BPH were counted as dead if they were unable to walk or jump after stimulation. Directly after the mortality assessment all BPH adults and nymphs were removed from each plant. Any new plant growth was removed by cutting the leaves with scissors.
  • test containers were then re-incubated at 25°C with a 16-hour photoperiod, and the number of L1/L2 nymphs present on the plants 18 days after the original infestation were counted and recorded to provide a mean percentage nymph emergence compared to the control.
  • Nilaparvata lugens by pymetrozine Whilst limited control of late instar (L5) Nilaparvata lugens by pymetrozine is observed (a maximum of 40% mortality observed 7 days after treatment at the highest concentration tested), excellent control of BPH is achieved through inhibition of the ability of BPH to lay eggs. This is shown by the data for mean percentage control of nymph emergence 18 days after treatment.
  • EXAMPLE B2 Determination of Pymetrozine metabolic cross resistance to neonicotinoids
  • the metabolic capacity of neonicotinoid-susceptible and -resistant brown planthopper (BPH, Nilaparvata lugens) populations was compared to appraise the potential of metabolic cross resistance against pymetrozine.
  • the following populations of insects were tested: (i) Population of Nilaparvata lugens collected from the field in India in 2005, and which demonstrated 5200-fold resistance to the neonicotinoid insecticide imidacloprid (Indian NNI-R BPH);
  • a calibration with pymetrozine and imidacloprid and the primary hydroxy imidacloprid metabolite were produced to convert LCMS peak area values into known weights.
  • the primary hydroxyl pymetrozine metabolite is expressed in peak area as no authentic compound was available.
  • Susceptible and resistant strains are clearly delineated by production of the primary imidacloprid metabolite with the following fold differences compared to the susceptible shown in Table 1.
  • Table 2. The relative amount of the primary hydroxy imidacloprid metabolite produced in the BPH strains where the amount in ng/mg hopper has been converted to a ratio to allow comparison to the susceptible strain.
  • Metabolism peaks at 5.5 hours with 27 and 20-fold higher production of the primary metabolite in the Vietnam and India strains respectively, compared to the susceptible. It's likely that further metabolism of the primary metabolite occurs accounting for the drop in levels after 17 hours. Typically this could be glucose conjugation at the hydroxyl group to form a more polar compound for excretion.

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Abstract

L'invention porte sur un procédé qui permet de lutter contre les insectes résistants aux insecticides néonicotinoïdes à l'aide du composé 4,5-dihydro-6-méthyl-4-(3-pyridylméthylèneamino)-1,2,4-triazin-3(2H)-one sous forme libre ou sous la forme d'un sel agrochimiquement acceptable, et sur l'utilisation de compositions renfermant ledit composé pour lutter contre les insectes résistants aux néonicotinoïdes. Les procédés selon l'invention concernent, en particulier, la lutte contre les insectes résistants aux néonicotinoïdes des familles Delphacidae et Cicadellidae, notamment les fulgores (p.ex. les insectes du genre Nilaparvata, Sogatella et/ou Laodeiphax), et/ou les cicadelles résistantes à un ou plusieurs insecticides néonicotinoïdes. Les procédés selon l'invention trouvent un usage particulier dans la lutte contre les insectes résistants aux néonicotinoïdes dans les cultures de plantes utiles, en particulier les céréales, y compris le riz. L'invention se rapporte en outre à des procédés de lutte contre les virus des végétaux diffusés par les insectes résistants aux néonicotinoïdes.
PCT/GB2009/001401 2008-06-19 2009-06-04 Procédés de lutte contre les insectes résistants aux néonicotinoïdes WO2009153539A2 (fr)

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CN2009801275831A CN102098920A (zh) 2008-06-19 2009-06-04 防治新烟碱类抗性昆虫的方法
KR1020117001121A KR20110018948A (ko) 2008-06-19 2009-06-04 네오니코티노이드 내성 곤충의 방제 방법

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AU2012351537B2 (en) * 2011-12-16 2017-03-02 Nanobiotix Nanoparticles comprising metallic and hafnium oxide materials, preparation and uses thereof
CN106699765B (zh) * 2016-12-14 2018-07-10 山东省联合农药工业有限公司 一种新型烟碱类杀虫剂及其制备方法和用途

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WO2011134816A1 (fr) 2010-04-27 2011-11-03 Syngenta Participations Ag Méthodes de maîtrise de pucerons résistants aux néonicotinoïdes
CN102869259A (zh) * 2010-04-27 2013-01-09 先正达参股股份有限公司 控制耐新烟碱的蚜虫的方法
US20130196999A1 (en) * 2010-04-27 2013-08-01 Syngenta Crop Protection Llc Methods of controlling neonicotinoid resistant aphids

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WO2009153539A3 (fr) 2010-12-16
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