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WO2004082383A1 - Utilisation de triazolopyrimidines pour combattre les nematodoses de vegetaux - Google Patents

Utilisation de triazolopyrimidines pour combattre les nematodoses de vegetaux Download PDF

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WO2004082383A1
WO2004082383A1 PCT/EP2004/002581 EP2004002581W WO2004082383A1 WO 2004082383 A1 WO2004082383 A1 WO 2004082383A1 EP 2004002581 W EP2004002581 W EP 2004002581W WO 2004082383 A1 WO2004082383 A1 WO 2004082383A1
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alkyl
alkenyl
nitrogen atoms
halogen
alkoxy
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Henry Van Tuyl Cotter
Mark R. Schmitt
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BASF SE
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BASF SE
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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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the invention relates to a method of use of triazolopyrimidines of formula I
  • R 1 denote halogen, hydroxyl, C . -C 10 -alkyl, C 2 -C . o-alkenyl, C 2 -C 10 -alkynyl, C C 10 - haloalkyl, C 2 -G 10 -haloalkenyl, C 3 -C 10 -cycloalkyl, phenyl, naphthyl,
  • a 5- or 6-membered saturated, unsaturated, or aromatic heterocycle containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom, or
  • R A and R B independently denote hydrogen, C-rC 10 -alkyl, C 2 -C ⁇ 0 -alkenyl, C 2 -C 0 - alkynyl, C . -C . o-haloalkyl, C 2 -C 10 -haloalkenyl, C 3 -C 10 -cycloalkyI, phenyl, naphthyl, a 5- or 6-membered saturated, unsaturated, or aromatic heterocycle, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom, or
  • R A and R B together with the interjacent nitrogen atom represent a 5- or 6- membered saturated or unsaturated heterocycle, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom, which ring may be substituted by one to three R a radicals, or in which ring two adjacent atoms may be connected by a C C 4 -alkylene group;
  • R a is cyano, nitro, halogen, hydroxyl, C . -C 6 -alkyl, C ⁇ -C 6 -halogenalkyl,
  • A is hydrogen, hydroxyl, halogen, C C 6 -alkyl, C 2 -C ⁇ o-alkenyl, C C 6 -alkoxy, C ⁇ -C 10 -haloalkoxy, C.-C 6 -alkylamino, or di-(C ⁇ -C 6 - alkyl)amino;
  • R 2 denote C.-C 10 -alkyl, C 2 -C 1Q -alkenyl, C 2 -C 10 -alkynyl, C t -Cio-haloalkyl, C 2 -C ⁇ 0 -halo- alkenyl, which radicals may be unsubstituted or may carry one to five groups R a ; or
  • Cs-do-cycloalkyl phenyl, naphthyl, a 5- or 6-membered saturated, unsaturated, or aromatic heterocycle, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom, which cyclic groups may be unsub- stituted or may carry one to four groups R b :
  • R b is cyano, nitro, halogen, hydroxyl, C.-C 6 -alkyl, C 3 -C 6 -cycloalkyl, C C 6 - alkoxy, C r C 6 -alkylthio, C.-C 6 -alkylsulfonyl . C ⁇ -C 6 -alkylsulfoxyl, C .
  • A' is hydroxyl, halogen, C 2 -C 10 -alkenyl, d-C.o-haloalkoxy, C . -C 6 - alkylamino, or di-(C ⁇ -C 6 -alkyl)amino;
  • R 3 denote halogen, hydroxyl, cyano, C C ⁇ -alkyl, C 2 -C 10 -alkenyl, C 2 -C ⁇ _-alkynyl, C ⁇ -C 6 -alkoxy, C C 6 -alkylthio, NR A R B , OR A , or SR A ;
  • n is zero, 1 , or 2; wherein R 1 , R 3 , R A and R B radicals may be unsubstituted or may carry one to five groups R a ;
  • the invention relates to a method for the protection of plants from attack or infestation by nematode pests which comprises applying to the foliage, shoot, root or seed of the plants, or to the soil or water in which they are growing, an effective amount of compounds of formula I.
  • an object of the present invention to provide a method for combating nematode diseases of plants.
  • Triazolopyrimidines are generally known from US 4 567 263, US 5 593 996, EP-A 613 900, US 5 994 360, WO 99/41255, EP-A 1249 452, WO 03/004465, WO 03/009687, and DE-Appln. No. 102 52 261.8.
  • the compounds disclosed in the documents discussed above are active against various phytopathogenic fungi. However, prior art does not describe or suggest that these compounds may be effective against nematode diseases of plants.
  • - C ⁇ -C 10 -alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 10, preferably 1 to 6 carbon atoms, especially C C 4 -alkyl, such as methyl, ethyl, pro- pyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, or pentyl, 1-methylbutyl, 2-m ⁇ thylbutyl, 3-methylhutyl, 2,2-di-methylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethyl- butyl, 2,3-dimethylbutyl,
  • C 3 -C 4 -alkenyl for example ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl and 2-methyl-2-propenyl;
  • o-alkynyl straight-chain or branched hydrocarbon radicals having 2 to 10, pref- erably 2 to 4 carbon atoms and a triple bond in any position, especially C 3 -C 4 -alkynyl, for example ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1 -methyl-2-propynyl;
  • o-cycloalkyl mono- or bicyclic cycloalkyl groups having 3 to 10 carbon atoms; monocyclic groups preferably have 3 to 8, especially 3 to 6 ring members, bicyclic groups preferably have 8 to 10 ring members, for example C 3 -C 8 -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom
  • 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitro- gen atoms and one sulfur or oxygen atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,2,4-oxadiazol-3-yl
  • 6-membered heteroaryl containing one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • 6-membered heteroaryl groups which, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazin
  • R 1 represents halogen, straight-chained or branched C ⁇ -C 10 -alkyl, in particular a branched C 3 -G .0 -alkyl group, C 3 -C 8 -cycloalkyl, Cpdo-haloalkyl or NR A R B , phenyl being optionally substituted by one to three halogen, hydroxyl, or C C 10 -alkyl or C t -C-io-alkoxy groups.
  • R 1 represents NR A R B
  • R A and R B are identical or different and denote G.-C 6 -alkyl, C 4 -C 6 -alkenyl, C 5 -C 6 -cycloalkyl, C.-C 6 - haloalkyl, or phenyl which may be substituted by halogen or alkyl, the carbon chains of R A and R B radicals may be substituted by phenyl.
  • R A denotes C.-C 10 -haloalkyl, preferably a polyfluorinated alkyl group, 2,2,2-trifluoro- ethyl, 2-(1 ,1 ,1-trifluoropropyl) or 2-(1 ,1 ,1-trifluorobutyl) group are particularly preferred.
  • NR A R B represents an optionally substituted heterocycle, preferably an optionally substituted OrC heterocyclic ring bonded via a nitrogen atom to the triazolopyrimidine moiety, in particular a pyrrolidine, or piperidine, in particular 1-piperidinyl or morpholinyl ring which may be substituted by one or more R a groups, especially by hydroxyl, or C C 4 -alkyl groups.
  • R 2 is straight-chained or branched CrC- ⁇ -alkyl, or phenyl which may be substituted by halogen, especially chloro or fluoro, C C 4 -alkyl, C C ⁇ alkoxy, C-r rhaloalkyt, di-C C -alkylamino, HOOC-C C.o-alkoxy, wherein at least one substituent is in ortho position.
  • R 2 is methyl, ethyl, branched C- 3 -C-e-alkyl, or a group G:
  • L 1 to L 5 independently denote hydrogen, halogen, methyl, methoxy, dimethyl- amino, (4-methyl)-1-piperidinyl, or HOOC-CrC . o-alkoxy, and # marks the bond to the triazolopyrimidine system, wherein at least one of L 1 to L 5 is not hydrogen.
  • L 3 is hydrogen, halogen, methyl, methoxy, dimethylamino, HOOC-C 2 -C 8 -alkoxy,
  • A is hydroxyl, halogen, C 2 -C 10 -alkenyl, C C 6 -alkylamino, or di-(Ct-C 6 -alkyl)amino.
  • R 3 is halogen, methoxy, thiomethyl, or NR A R B which represents an optionally substituted heterocycle, preferably an optionally substituted C 3 -C 7 -heterocyclic ring, in particular a pyrrolidine, or piperidine, in particular 1-piperi- dinyl or morpholinyl ring which may be substituted by one or more hydroxy, or C.-C 4 -alkyl groups, are preferred. Besides, particular preference is given to compounds I in which R 3 represents a chloro atom.
  • R 3 is halogen, meth- oxy, or thiomethyl, especially chloro.
  • R 4 is hydrogen or mercapto, preferably hydrogen.
  • Plant parasitic nematodes such as root-knot nematodes, Meloidogyne arenaria, Melopidogyne chitwoodi, Meloidogyne exigua, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other Meloidogyne species; cyst nematodes, Giobodera rostochiensis, G bodera palli ⁇ a, Globodera tabacum and other Giobodera species, Heterodera avenae, Heterodera glycines, Heterodera schac iii, Heterodera trifolii, and other Heterodera species; seed gall nematodes, Anguina f nesta, Anguina tritici and other Anguina species; stem and foliar nematodes
  • Radinaphelenchus species burrowing nematodes, Radopholus similis and other Ra- dopholus species; reniform nematodes; Scutellonema species; stubby root nematodes, Trichodorus primitivus and other Trichodorus species; Paratrichodorus minor and other Paratrichodorus species; stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhyn- chus dubius and other Tylenchorhynchus species and Merlinius species; citrus nematodes, Tylenchulus semipenetrans and other Tylenchulus species; dagger nematodes, Xiphinema americanum, Xiphinema index, Xiphinema diversicaudatum and other Xiphi- nema species; and other plant parasitic nematode species.
  • ppm to 10 000 ppm and preferably 1 ppm to 5000 ppm of formula I compounds, dispersed in water or another liquid carrier is effective when applied to plants, seeds or the soil or water in which the plants are growing or are to be grown to protect the plants from nematode attack and infestation.
  • the triazolopyrimidines are also effective for protecting plants from attack or infestation by nematodes when applied to the foliage, stem or roots of the plants and/or to the soil or water in which said plants are growing or are to be grown in sufficient amount to provide a rate of 0.01 kg/ha to 100 kg/ha, preferably from 0.1 to 3.0 kg/ha, of active ingredient.
  • amounts of active ingredient are from 0,001 to 10 g, preferably 0,01 to 1 g, are generally required per kilogram of seed.
  • the compounds I are usually applied in customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • customary formulations e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the use form depends on the particular purpose; in any case, it should guarantee a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, e.g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent.
  • auxiliary solvents e.g. water is used as the diluent.
  • Auxiliaries which are suitable are essentially: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. mineral oil frac- tions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g.
  • ethanolamine, dimethylformamide and water
  • carriers such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic minerals (e.g. highly-disperse silica, silicates); emulsifiers such as non-ionic and anionic emulsifiers (e.g. poly- oxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.
  • Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of ligno- sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of napthalenesulfonic acid with phenol or formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octyl- phenol, nonylphenol, alkyl
  • Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g.
  • strongly polar solvents e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.
  • Powders, materials for scattering and dusts can be prepared by mixing or concomi- tantly grinding the active substances with a solid carrier.
  • Granules e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay
  • the formulations comprise of from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient.
  • the active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the formulations may contain adjuvants, such as those known from EP-A 943241 , and WO 0/018227. In such formulations formula I compounds show an enhanced efficacy.
  • the formulations comprise of from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient.
  • the active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the active ingredient concentrations in the ready-to-use products can be varied within substantial ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1 %.
  • formula I compounds of this invention are effective for controlling nematode diseases of agronomic and horticultural crops, and non-crop plants, when employed alone, they may also be used in combination with other biological agents used in agri- culture, including other nematicides, insecticides and/or acaricides. Mixing the compounds I or the compositions comprising them in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.
  • the formula I compounds may be used effectively in conjunction or com- bination with pyrethroids, phosphates, carbamates, cyclodienes, formamidines, phenol tin compounds, chlorinated hydrocarbons, ben ⁇ oylphenyl ureas, pyrroles and the like.
  • pesticides together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations by way of example:
  • fumigant nematicidal compounds such as chloropicrin, dazomet, 1 ,3-dichloropropene, ethylene dibromide, metam, methyl bromide, methyl iodide, methyl isothocyanate, and sodium tetrathio(peroxocarbonate), carbamate nematicidal compounds such as aldicarb, carbofuran, carbosulfan, and ox- amyl, organophosphate nematicidal compounds such as cadusafos, ethoprophos, fenami- phos, fosthiazate, phorate, terbufos, and triazophos, other chemical nematicidal materials, such as abamectin and benclothiaz, biological nematicidal materials such as Myrothecium verrucaria compositions, bacte- rial pathogens of nematodes including but not limited to Past
  • Organophosphates such as Acephate, Azinphos-methyl, Chlorpyrifos, Chlorfenvinphos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Fenitrothion, Fen- thion, Isoxathion, Malathion, Methamidophos, Methidathion, Methyl-Parathion, Mevin- phos, Monocrotophos, Oxydemeton-methyl .
  • Carbamates such as Alanycarb, Benfuracarb, Carbaryl, Carbosulfan, Fenoxycarb, Furathiocarb, Indoxacarb, Methiocarb, Methomyl, Oxamyl, Pirimicarb, Propoxur, Thio- dicarb, Triazamate;
  • Pyrethroids such as Bifenthrin, Cyfluthrin, Cypermethrin, Deltamethrin, Esfenvalerate, Ethofenprox, Fenpropathrin, Fenvalerate, Cyhalothrin, Lambda-Cyhaiothrin, Perme- thrin, Silafluofen, Tau-Fluvalinate, Tefluthrin, Tralomethrin, Zeta-Cypermethrin;
  • Arthropod growth regulators a) chitin synthesis inhibitors: benzoylureas: Chlorfluazuron, Diflube ⁇ zuron, Flucy- cloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflu- muron; Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Clofentazine; b) ecdysone antagonists: Halofenozide, Methoxyfenozide, Tebufenozide; c) juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: Spirodiclofen;
  • the formula I compounds may also be used in combination or conjunction with one or more other parasiticidal compounds including anthelmintics, such as benzimidazoles, piperazine, levamisole, pyrantel, pra ⁇ iquantel and the like; endectocides such as aver- mectins, milbemycins and the like; ectoparasiticides such as arylpyrroles, organophos- phates, carbamates, gamabutyric acid inhibitors including fipronil, pyrethroids, spino- sads, imidacloprid and the like; insect growth regulators such as pyriproxyfen, cyromazine and the like; and chitin synthase inhibitors such as benzoylureas, such as flufenoxuron.
  • anthelmintics such as benzimidazoles, piperazine, levamisole, pyrantel, pra ⁇ iquantel and the like
  • the formula I compounds may also be used in combination or conjunction with one or more other fungicidal compounds including, but not limited to sulfur, dithiocarbamates and their derivatives, such as iron(lll)dimethyldithiocarbamate, zinc dimethyldithiocar- ba ate, zincethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N.N'-propylenebisdithiocarbarnate), zinc (N,N'-propylenebisdithiocarbamate), N,N'- polypropylenebis(thiocarbamoyl)disulfide; nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4
  • 2-lrichloroethylfugl piperazine-1 ,4-diylbis-1-(2,2,2-.rich.oro- elhyl)formamide, 1-(3,4-dichloroanilino)-1 -formylamino-2,2,2-trichloroethane; 2,6-di- methyl-M-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2 f 6-dimethyl- morpholine, N-[3-(p- tert-butylphenyl)-2-methylpropyl]-piperidine, 8-tert.-butyl-1,4-dioxaspiro[4.5]decan-2- ylmethyl(ethyl)(propyl)amine, (RS)-2-[2-(
  • the formula I compounds may also be used in combination or conjunction with one or more compounds selected from piperonyl butoxide, N-octyl bicycloheptene dicarbox- imide, dipropyl pyridine-2,5-dicarboxylate and 1 ,5a,6,9,9a,9b-hexahydro-4a(4H)-di- benzofurancarboxaldehyde to broaden the spectrum of activity.
  • the formula I compounds may also be used in combination or conjunction with one or more other herbicidal compounds including, but not limited to alloxydim, clethodim, cloproxydim, cycloxydim, sethoxydim, tralkoxydim, butroxydim, clefoxydim, tepraloxy- dim, clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenthiapropethyl, fluazifop-butyl, fluazifop-P-butyl, haloxyfop- ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, isoxapyrifop, propaquizafop, qui- zalofop-ethyl, quizalofop
  • compositions which may be used in the present invention include a parasiticidally effective amount of a formula I compound or combinations thereof admixed with one or more agronomically acceptable tolerable inert, solid or liquid carriers.
  • Such compositions may comprise further additives, such as stabilizers, anifoams, viscosity regulators, binders and takifiers.
  • stabilizers, anifoams, viscosity regulators, binders and takifiers such as stabilizers, anifoams, viscosity regulators, binders and takifiers.
  • Trial 1 Greenhouse soil nematicide assay targeting root-knot nematode Meloidogyne sp. on tomato
  • test compounds were solubilized in acetone and diluted with water and surfactant to the required test concentrations.
  • the test solution was applied as a soil drench to transplanted tomato plants (variety Bonny Best) in cells with sandy loam mixed with sand.
  • One thousand root-knot J2 larvae were applied as an aqueous suspension drenched on the soil surface later the same day as treatment.
  • the plants were maintained in the greenhouse and, 2-3 weeks after inoculation, the plant roots were washed free of soil. The root-knot galls on the root system of each plant were counted.
  • Percent control of root knot was calculated for the treated plants relative to control plants treated with the acetone-surfactant carrier using the following formula:
  • T median number of galls on treated plants
  • Phytotoxicity evaluations were also made. Plant phytotoxicity evaluations were made one week after treatment and root phytotoxicity evaluations were made when the root systems were harvested. Root and/or shoot stunting was observed for many of the compounds.
  • test compounds were solubilized in acetone and diluted with water and surfactant to the required test concentrations.
  • the test solution was applied as a soil drench to transplanted soybean plants (variety Hutcheson) in cells with sandy loam mixed with sand.
  • One thousand root-knot J2 larvae were applied as an aqueous suspension drenched on the soil surface later the same day as treatment.
  • the plants were maintained in the greenhouse and, 4 weeks after inoculation, the nematode cysts were ex- tracted from the root system and soil using sieves. The cysts extracted from each root- soil system were counted.
  • Percent control of soybean cyst was calculated for the treated plants relative to control plants treated with the acetone-surfactant carrier using the formula given above.
  • Phytotoxicity evaluations were also made. Plant phytotoxicity evaluations were made one week after treatment and root phytotoxicity evaluations were made when the cysts were harvested. Root and/or shoot stunting was observed for many of the compounds.

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Cette invention concerne un procédé d'utilisation de triazolopyrimidines représentées par la formule (I) dans laquelle R1 désigne halogène, hydroxy, alkyle, alcényle, alkynyle, haloalkyle, haloalcényle, cycloalkyle, phényle, naphthyle, un hétérocycle aromatique, saturé ou insaturé à 5 ou 6 chaînons, contenant entre 1 et 4 atomes d'azote ou entre 1 et 3 atomes d'azote et un atome de soufre ou d'oxygène, ou NRARB, ORA ou SRA, RA et RB désignant indépendamment hydrogène, alkyle, alcényle, alkynyle, haloalkyle, haloalcényle, cycloalkyle, phényle, naphthyle, un hétérocycle aromatique, saturé ou insaturé à 5 ou 6 chaînons, contenant entre 1 et 4 atomes d'azote ou entre 1 et 3 atomes d'azote et un atome de soufre ou d'oxygène, ou RA et RB, associés à l'atome d'azote intercalé, désignant un hétérocycle saturé ou insaturé à 5 ou 6 chaînons, contenant entre 1 et 4 atomes d'azote ou entre 1 et 3 atomes d'azote et un atome de soufre ou d'oxygène, ledit noyau pouvant être substitué de la manière définie dans la description ; R2 désigne alkyle, alcényle, alkynyle, haloalkyle, haloalcényle, cycloalkyle, phényle, naphthyle, un hétérocycle aromatique, saturé ou insaturé à 5 ou 6 chaînons, contenant entre 1 et 4 atomes d'azote ou entre 1 et 3 atomes d'azote et un atome de soufre ou d'oxygène ; R3 désigne halogène, hydroxy, cyano, alkyle, alcényle, alkynyle, alcoxy, alkylthio, NRARB ; R4 désigne hydrogène, cyano, hydroxy, mercapto, alcoxy, alkylthio, haloalcoxy, NRARB, S(=O)nG, G étant tel que défini dans la description, les radicaux R1, R2, R3, RA et RB pouvant être substitués ou non substitués selon leur définition dans la description. Les composés de la présente invention servent à combattre les nématodoses de végétaux. Cette invention concerne également un procédé visant à protéger les végétaux en croissance contre les attaques des nématodes et contre les infestations par les nématodes, lequel procédé consiste à appliquer sur le feuillage des végétaux ou sur la terre ou dans l'eau constituant leur milieu de croissance, une quantité efficace de composés représentés par la formule (I).
PCT/EP2004/002581 2003-03-17 2004-03-12 Utilisation de triazolopyrimidines pour combattre les nematodoses de vegetaux Ceased WO2004082383A1 (fr)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008099902A1 (fr) 2007-02-15 2008-08-21 Ishihara Sangyo Kaisha, Ltd. Dérivé de pyridyl-triazolopyrimidine ou son sel, pesticide la contenant et son procédé de production
WO2010018853A1 (fr) * 2008-08-13 2010-02-18 石原産業株式会社 Dérivé pyridyle-triazolopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nocifs le comprenant
WO2019149660A1 (fr) 2018-02-02 2019-08-08 Boehringer Ingelheim International Gmbh Dérivés de triazolopyrimidine destinés à être utilisés en tant qu'inhibiteurs de la ghréline o-acyltransférase (goat)
US11136337B2 (en) 2018-02-02 2021-10-05 Boehringer Ingelheim International Gmbh Pyrazole- and indazole-substituted oxadiazolopyridine derivatives for use as ghrelin O-acyl transferase (GOAT) inhibitors
US11254688B2 (en) 2018-02-02 2022-02-22 Boehringer Ingelheim International Gmbh Benzyl-, (pyridin-3-yl)methyl -or (pyridin-4-yl)-methyl-substituted oxadiazolopyridine derivatives as ghrelin O-acyl transferase (GOAT) inhibitors
US11319310B2 (en) 2018-02-02 2022-05-03 Boehringer Ingelheim International Gmbh Heterocyclyl-substituted oxadiazolopyridine derivatives for use as ghrelin O-acyl transferase (GOAT) inhibitors
US11518771B2 (en) 2020-05-22 2022-12-06 Boehringer Ingelheim International Gmbh Process for manufacturing alkyl 7-amino-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridine-carboxylate
US11976082B2 (en) 2020-05-22 2024-05-07 Boehringer Ingelheim International Gmbh Continuous process for manufacturing alkyl 7-amino-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridine-carboxylate

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993004583A1 (fr) * 1991-09-03 1993-03-18 Dowelanco Procede nematicide
WO1996035690A1 (fr) * 1995-05-09 1996-11-14 Basf Aktiengesellschaft PYRAZOLO-(1,5a)-PYRIMIDINES, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION
WO2002050077A2 (fr) * 2000-12-18 2002-06-27 Bayer Cropscience Ag Triazolopyrimidines

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993004583A1 (fr) * 1991-09-03 1993-03-18 Dowelanco Procede nematicide
WO1996035690A1 (fr) * 1995-05-09 1996-11-14 Basf Aktiengesellschaft PYRAZOLO-(1,5a)-PYRIMIDINES, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION
WO2002050077A2 (fr) * 2000-12-18 2002-06-27 Bayer Cropscience Ag Triazolopyrimidines

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008099902A1 (fr) 2007-02-15 2008-08-21 Ishihara Sangyo Kaisha, Ltd. Dérivé de pyridyl-triazolopyrimidine ou son sel, pesticide la contenant et son procédé de production
JP2008222707A (ja) * 2007-02-15 2008-09-25 Ishihara Sangyo Kaisha Ltd ピリジル−トリアゾロピリミジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法
US8124760B2 (en) 2007-02-15 2012-02-28 Ishihara Sangyo Kaisha, Ltd. Pyridyl-triazolopyrimidine derivative or its salt, pesticide containing it and its production process
WO2010018853A1 (fr) * 2008-08-13 2010-02-18 石原産業株式会社 Dérivé pyridyle-triazolopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nocifs le comprenant
US11136337B2 (en) 2018-02-02 2021-10-05 Boehringer Ingelheim International Gmbh Pyrazole- and indazole-substituted oxadiazolopyridine derivatives for use as ghrelin O-acyl transferase (GOAT) inhibitors
CN111683951A (zh) * 2018-02-02 2020-09-18 勃林格殷格翰国际有限公司 用作饥饿素o-酰基转移酶(goat)抑制剂的三唑并嘧啶衍生物
WO2019149660A1 (fr) 2018-02-02 2019-08-08 Boehringer Ingelheim International Gmbh Dérivés de triazolopyrimidine destinés à être utilisés en tant qu'inhibiteurs de la ghréline o-acyltransférase (goat)
US11254688B2 (en) 2018-02-02 2022-02-22 Boehringer Ingelheim International Gmbh Benzyl-, (pyridin-3-yl)methyl -or (pyridin-4-yl)-methyl-substituted oxadiazolopyridine derivatives as ghrelin O-acyl transferase (GOAT) inhibitors
US11319310B2 (en) 2018-02-02 2022-05-03 Boehringer Ingelheim International Gmbh Heterocyclyl-substituted oxadiazolopyridine derivatives for use as ghrelin O-acyl transferase (GOAT) inhibitors
US11583532B2 (en) 2018-02-02 2023-02-21 Boehringer Ingelheim International Gmbh Triazolopyrimidine derivatives for use as ghrelin o-acyl transferase (GOAT) inhibitors
CN111683951B (zh) * 2018-02-02 2023-10-13 勃林格殷格翰国际有限公司 用作饥饿素o-酰基转移酶(goat)抑制剂的三唑并嘧啶衍生物
US11518771B2 (en) 2020-05-22 2022-12-06 Boehringer Ingelheim International Gmbh Process for manufacturing alkyl 7-amino-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridine-carboxylate
US11976082B2 (en) 2020-05-22 2024-05-07 Boehringer Ingelheim International Gmbh Continuous process for manufacturing alkyl 7-amino-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridine-carboxylate

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