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
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • 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 invention relates to a method of use of 2-substituted pyrimidines of formula I
• R 1 denotes a five- to ten-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle comprising one to four hetero atoms selected from the group consisting of O, N or S, except for pyridyl, it being possible for R 1 to be substituted by one to three identical or different groups R a ,
• R a is halogen, hydroxyl, cyano, oxo, nitro, amino, mercapto, C r C 6 -alkyl, CrCe-haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 - alkoxy, CVC ⁇ -haloalkoxy, carboxyl, Ci-C 6 -alkoxycarbonyl, carbamoyl, d-Ce-alkylaminocarbonyl, C-rCe-alkyl-CrCe-alkylamincarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, C-i-Ce-alkylcarbonylamino,
• Ci-C 6 -alkylamino di(C 1 -C 6 -alkyl)amino, CrC 6 -alkylthio, C 1 -C 6 - alkylsulfinyl, Ci-C 6 -alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, C 1 - C 6 -alkylaminosulfonyl or di(Ci-C 6 -alkyl)aminosulfonyl;
• R 2 denotes halogen, cyano, Ci-Ce-alkyl, Ci-C 6 -haloalkyl, C r C 6 -alkoxy, C 1 -C 4 - haloalkoxy or C 3 -C 6 -alkenyloxy;
• R 3 , R 4 independently denote hydrogen, C r C 6 -alkyl, C r C 6 -haloalkyl, C 3 -C 6 - cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 - alkynyl or C 2 -C 6 -haloalkynyl, or
• R 3 and R 4 together with the nitrogen atom to which they are bonded, form a five- or six-membered ring (heterocycle) which can be interrupted by a hetero atom selected from the group consisting of O, N and S and/or which can have attached to it one or more substituents selected from the group consisting of halogen, C-i-C ⁇ -alkyl, C ⁇ Ce-haloalkyl and oxy-C-i-C 3 -alkylenoxy or in which ring two adjacent C atoms or one N atom and one adjacent C atom can be linked by a C 1 -C 4 -alkylene chain;
• R 5 , R 6 independently denote hydrogen, halogen, Ci-C 6 -alkyl, C ⁇ Ce-haloalkyl or C 1 - C 6 -alkoxy
• R 7 , R 8 independently denote hydrogen, halogen, C r C 6 -alkyl or C r C 6 -haloalkyl
• R 9 denotes hydrogen, halogen, Ci-C 6 -alkyl, C r C 6 -alkoxy, C 3 -C 6 -cycloalkoxy, C 1 -C 6 -IIaIOaIkOXy, d-C ⁇ -alkoxycarbonyl or d-Ce-alkylaminocarbonyl,
• 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, an effective amount of compounds of formula I.
• Nematode pests destroy crops including growing, harvested and dormant crops. In spite of the commercial pesticides available today, damage to crops still occurs. Accordingly, there is ongoing research to create new and more effective pesticides.
• an object of the present invention to provide a method for combating nematode diseases of plants.
• 2-Substituted pyrimidines are generally known from WO-A 02/07453.
• the compounds disclosed in this document are active against various phytopathogenic fungi. However, the document does not describe or suggest that these compounds may be effective against nematode diseases of plants.
• halogen fluorine, chlorine, bromine or iodine
• alkenyl and the alkenyl moieties of alkenyloxy unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6, preferably 2 to 4 carbon atoms, and a double bond in any position, especially 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;
• alkynyl straight-chain or branched hydrocarbon radicals having 2 to 6, preferably 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;
• - cycloalkyl mono- or bicyclic hydrocarbon radicals having 3 to 10 carbon atoms; monocyclic groups having 3 to 8, especially 3 to 6 ring members, for example C 3 -C 8 - cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
• haloalkyl and the haloalkyl moieties of haloalkoxy straight-chain or branched alkyl groups having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, especially 1 to 4 carbon atoms (as mentioned above), where the hydrogen atoms in these groups may be partially or fully replaced by halogen atoms as mentioned above, for example C 1 -C 2 - haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro
• - haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6, preferably 2 to 4 carbon atoms, and a double bond in any position (as mentioned above), where the hydrogen atoms in these groups may be partially or fully replaced by halogen atoms as mentioned above;
• - haloalkynyl straight-chain or branched hydrocarbon radicals having 2 to 6, preferably 2 to 4 carbon atoms, and a triple bond in any position (as mentioned above), where the hydrogen atoms in these groups may be partially or fully replaced by halogen atoms as mentioned above;
• halocycloalkyl mono- or bicyclic hydrocarbon radicals having 3 to 10 carbon atoms; monocyclic groups having 3 to 8, especially 3 to 6 ring members (as mentioned above), where the halogen atoms in these groups may be partially or fully replaced by halogen atoms as mentioned above;
• - oxy-alkyleneoxy divalent straight-chain hydrocarbon radicals having 1 to 3 carbon atoms, eg. OCH 2 CH 2 O or OCH 2 CH 2 CH 2 O;
• heterocycle such as 5- or 6-membered heterocycle: homo- or bicyclic hydrocarbon radicals containing one to four heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom; unsaturated (heterocyclyl) includes partially unsaturated, e.g. mono-unsaturated, and aromatic (heteroaryl); said heterocycles in particular include:
• 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 nitrogen 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, 1 ,2,
• 3-pyrazolidinyl 4-pyrazolidinyl, 5-pyrazolidinyl, 2-pyrrolodin-2-yl, 2-pyrrolodin-3-yl, 3- pyrrolodin-2-yl, 3-pyrrolodin-3-yl, 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyridin(1 ,2-dihydro)-2-on-1-yl, 2- piperazinyl, 1-pyrimidinyl, 2-pyrimidinyl, morpholin-4-yl, thiomorpholin-4-yl.
• R 3 is hydrogen or C r C 10 -alkyl
• R 4 is hydrogen, C-i-Ce-alkyl, C 4 -C 6 -alkenyl, C-i-Ce-haloalkyl, C 5 -C 6 -cycloalkyl or phenyl.
• R 3 is hydrogen
• R 4 is C 1 -C 6 - haloalkyl.
• R 4 denotes CrC ⁇ -haloalkyl or, preferably, a polyfluorinated alkyl group
• the 2,2,2- trifluoroethyl, 2-(1 ,1 ,1-trifluoropropyl) or 2-(1 ,1 ,1-trifluorobutyl) group is particularly preferred.
• R 3 and R 4 together with the interjacent atom form a 5- or 6-membered heterocyclic ring, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom, preferably an optionally substituted heterocyclic ring bonded via a nitrogen atom to the pyrimidine moiety, in particular a pyrrolidinyl, piperidinyl or morpholinyl ring; substituents on said heterocyclic group especially include one or more C r C 6 -alkyl, preferably C 1 -C 4 -B ⁇ yI groups.
• R 5 , R 6 , R 7 , R 8 , R 9 independently are selected from the group consisting of hydrogen, halogen, especially chloro or fluoro, C-i-C 4 -alkyl (in particular methyl), C-
• R 5 and/or R 6 are/is not hydrogen.
• R 5 is halogen, methyl or methoxy
• R 6 is hydrogen, halogen or methyl
• R 7 is hydrogen
• R 8 is hydrogen
• R 9 is hydrogen, halogen, methyl or methoxy.
• R 2 is halogen, methoxy or thiomethyl, especially chloro.
• R 1 is a five- or six- membered aromatic heterocycle which may carry up to three substituents R a as defined above, wherein R a preferably is halogen, hydroxyl, cyano, nitro, amino, mercapto, C r C 6 -alkyl, C r C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, CVC ⁇ -alkoxy, Ci-C 6 -haloalkoxy, carboxyl, CrC 6 -alkoxycarbonyl, carbamoyl, C 1 -C 6 - alkylaminocarbonyl, CrC ⁇ -alkyl-Ci-Ce-alkylarnincarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, CrCe-alkylcarbonylaminD, CrC ⁇
• R 1 denotes pyrazolyl such as pyrazol-1-yl, pyrrolyl, imidazolyl such as imidazol-1-yl, 1 ,2,3-triazolyl such as 1 ,2,3- triazol-1-yl, 1 ,2,4-triazolyl such as 1 ,2,4-triazoM-yl, or tetrazolyl such as tetrazol-1-yl, which groups are bonded via C or N, or pyrimidin-2-yl, pyrazinyl or pyridazin-3-yl, with pyrazol-1-yl being especially preferred. All these groups may carry up to three substituents R a as defined above, with R a being in particular halogen, especially if R 1 is pyrazolyl.
• exemplified compounds include the compounds 1-1 to 1-100 as compiled in table I ("Tabeiie I") on pages 36 to 44 of WO-A 02/07453. All these exemplified compounds are incorporated herein by reference and thus form part of the present disclosure.
• the formula I compounds of this invention are useful for the control of plant parasitic nematodes and the plant diseases that they cause.
• 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, Globodera rostochiensis, Globodera pallida, Globodera tabacum and other Globodera species, Heterodera avenae, Heterodera glycines, Heterodera schacrrtii, Heterodera trifolii, and other Heterodera species; seed gall nematodes, Anguina funesta, Anguina tritici and other Anguina species; stem and foliar nemato
• Rotylenchulus species Scutellonema species; stubby root nematodes, T ⁇ chodor ⁇ s primitivus and other Trichodorus species; Paratrichodorus minor and other Paratrichodorus species; stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus 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 Xiphinema species; and other plant parasitic nematode species.
• 0.1 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 (foliage, shoot and/or root), 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 compounds I are also effective for protecting plants from attack or infestation by nematodes when applied to the foliage, shoot 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 g 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 (i.e. at least one compound of formula I) 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.
• solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. mineral oil fractions), 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. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.
• ground natural minerals e.g. kaolins, clays, talc, chalk
• ground synthetic minerals e.g. highly-disperse silica, silicates
• emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquor
• surfactants include alkali metal, alkaline earth metal and ammonium salts of lignosulfonic 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, octylphenol, nonylphenol, alkylphenol polyglycol
• Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions include, but are not restricted to, 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.
• Powders, materials for scattering and dusts can be prepared by mixing or concomitantly 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 943 241 , and WO 0/018227.
• adjuvants such as those known from EP-A 943 241 , and WO 0/018227.
• formula I compounds may show an enhanced efficacy.
• 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 agriculture, including other nematicides, insecticides and/or acaricides.
• the formula I compounds may be used effectively in conjunction or combination with pyrethroids, phosphates, carbamates, cyclodienes, formamidines, phenol tin compounds, chlorinated hydrocarbons, benzoylphenyl ureas, pyrroles and the like.
• the following list of 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 isothiocyanate, and sodium tetrathio(peroxocarbonate), carbamate nematicidal compounds such as aldicarb, carbofuran, carbosulfan, and oxamyl, organophosphate nematicidal com ⁇ pounds such as cadusafos, ethoprophos, fenamiphos, fosthiazate, phorate, terbufos, and triazophos, other chemical nematicidal materials, such as abamectin and benclothiaz, biological nematicidal materials such as Myrothecium verrucaria compo ⁇ sitions, bacterial pathogens of nematodes including but not limited to Pasteu
• organophosphates such as Acephate, Azinphos-methyl, Chlorpyrifos, Chlorfenvinphos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Fenitrothion, Fenthion, Isoxathion, Malathion, Methamidophos, Methidathion, Methyl- Parathion, Mevinphos, Monocrotophos, Oxydemeton-methyl, Paraoxon, Parathion, Phenthoate, Phosalone, Phosmet, Phosphamidon, Phorate, Phoxim, Pirimiphos- methyl, Profenofos, Prothiofos, Sulprophos, Trichlorfon;
• Pyrethroids such as Bifenthrin, Cyfluthrin, Cypermethrin, Deltamethrin, Esfenvalerate, Ethofenprox, Fenpropathrin, Fenvalerate, Cyhalothrin, Lambda-Cyhalothrin, Permethrin, Silafluofen, Tau-Fluvalinate, Tefluthrin, Tralomethrin, Zeta-Cypermethrin;
• Arthropod growth regulators a) chitin synthesis inhibitors: benzoylureas: Chlorfluazuron, Diflubenzuron,
• 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, praziquantel and the like; endectocides such as avermectins, milbemycins and the like; ectoparasiticides such as arylpyrroles, organophosphates, carbamates, gamabutyric acid inhibitors including fipronil, pyrethroids, spinosads, imidacloprid and the like; insect growth regulators such as pyriproxyfen, cyromazine and the like; and chitin synthase inhibitors such as benzoyl- ureas, such as flufenoxuron.
• anthelmintics such as benzimidazoles, piperazine, levamisole, pyrantel, praziquantel 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 dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N 1 N- ethylenebisdithiocarbamate), ammonia complex of zinc (N 1 N'- propylenebisdithiocarbamate), zinc (N,N'-propylenebisdithiocarbamate), N 1 N'- polypropylenebis(thiocarbamoyl)disulfide; nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,
• the formula I compounds may also be used in combination or conjunction with one or more compounds selected from piperonyl butoxide, N-octyl bicycloheptene dicarboximide, dipropyl pyridine-2,5-dicarboxylate and 1 ,5a,6,9,9a,9b-hexahydro- 4a(4H)-dibenzofurancarboxaldehyde 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, tepraloxydim, 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, quizalofop-ethyl, quizalofop-P-
• compositions which may be used in the present invention comprise an amount of a formula I compound effective in protecting plants from nematodes, 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. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations.
• Trial 1 Greenhouse soil nematicide assay targeting root-knot nematode Meloidogyne sp. on tomato
• the 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:
• 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. Plant stunting was observed for some 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 extracted 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.
• compound 1-1 of table I when applied at 10 kg/ha, provided almost complete control of soybean cyst nematode.

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• 2005
  • 2005-09-23 EP EP05786061A patent/EP1793676A1/en not_active Withdrawn
  • 2005-09-23 MX MX2007002980A patent/MX2007002980A/es not_active Application Discontinuation
  • 2005-09-23 BR BRPI0515526-6A patent/BRPI0515526A/pt not_active IP Right Cessation
  • 2005-09-23 WO PCT/EP2005/010332 patent/WO2006032526A1/en not_active Application Discontinuation
• 2007
  • 2007-02-21 IL IL181476A patent/IL181476A0/en unknown

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