WO2000023422A1 - Derives d'hydrazino-oxoacetamide et insecticide - Google Patents
Derives d'hydrazino-oxoacetamide et insecticide Download PDFInfo
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- WO2000023422A1 WO2000023422A1 PCT/JP1999/005760 JP9905760W WO0023422A1 WO 2000023422 A1 WO2000023422 A1 WO 2000023422A1 JP 9905760 W JP9905760 W JP 9905760W WO 0023422 A1 WO0023422 A1 WO 0023422A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Definitions
- the present invention relates to a hydrazine oxoacetamide derivative or a salt thereof, a method for producing the same, and a pesticide, in particular, a use as an insecticide.
- JP-A-10-67732 describes a compound represented by the following formula (V).
- WO 97/11050 describes a compound represented by the following formula (VI).
- EP 742202 describes a compound represented by the following formula (VII).
- VVII the insecticidal activity of these compounds is not always excellent. Further, compounds having excellent insecticidal activity are being studied.
- an object of the present invention is to provide a hydrazine oxoacetamide derivative or a salt thereof having a stronger insecticidal action than conventional insecticides.
- an object of the present invention is to provide a hydrazine oxoacetoamide derivative or a salt thereof, which exhibits an excellent insecticidal action against lepidopteran insects, coleopteran insects, and soil insects. Disclosure of the invention
- the present inventors have conducted extensive research on various hydrazine oxoacetoamide derivatives and the like for the purpose of developing a compound having a more excellent insecticidal activity than conventional hydrazine oxoacetoamide derivative-related compounds.
- a novel hydrazine oxoacetoamide derivative-related compound represented by the following formula (I) having excellent insecticidal activity has been found.
- the present invention has been made based on such new findings.
- R 1 is a chlorine atom or a bromine atom
- Y is oxygen or a methylene group; when Y is oxygen, p is 2; when Y is a methylene group, p is 0;
- R 2 is a trifluoromethyl group
- R 3 is hydrogen or a methyl group
- R 4 is hydrogen or methyl group
- R 5 is a methyl group, Echiru group, n- propyl group, cyclopropyl group, Ariru group or a propargyl group.
- the hydrazine oxoacetamide derivative of the present invention is represented by the above formula (I).
- the hydrazine oxoacetamide derivative of the present invention may exist as a syn-type or anti- type geometric isomer. Each of these geometric isomers may exist in a pure form or a mixed form of both.
- the present invention also includes a salt of a hydrazine oxoacetamide derivative.
- the salt examples include alkali metal salts such as sodium and potassium, and alkaline earth metal salts such as magnesium and calcium.
- Examples of the hydrazine oxoacetamide derivative of the present invention include the compounds described in Tables 1 and 2 below.
- the hydrazine oxoacetamide derivative of the present invention has the following formula (VIII):
- R 6 is an alkyl group, preferably 1 to 6 carbon atoms, particularly preferably 1 to 2 carbon atoms.
- Linear or branched alkyl groups such as methyl, ethyl, propyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl Group, isopentyl group, s-pentyl group, t-pentyl group, neopen 5760
- Preferable examples include a tyl group, an n-hexyl group, an isohexyl group, an s-hexyl group, a t-hexyl group, and a neohexyl group.
- VIII represented by the following formula:
- X represents a halogen (for example, a chlorine atom or the like), and R 7 represents a methyl group, an ethyl group, an n-propyl group, a cyclopropyl group, an aryl group or a propargyl group.
- R 7 represents a methyl group, an ethyl group, an n-propyl group, a cyclopropyl group, an aryl group or a propargyl group.
- reaction formula (1) As a raw material, for example, ⁇ N '— [(4-chlorophenyl) -1- (4-trifluoromethylsulfonyloxyphenyl) -methylene] —hydrazino ⁇ —oxoacetoxyacid methyl ester, and ethylamine When is used, it is expressed by the following reaction formula (1). Reaction formula (1)
- the compound of the general formula (IX) is a known compound and can be easily produced and obtained.
- the compound of the general formula (IX) can be used in a free form or a salt form.
- a suitable base can be used as a deoxidizing agent.
- Such examples include, for example, pyridine, triethylamine, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, potassium hydroxide, sodium hydroxide, sodium methylate, sodium methylate , Yuichi Shari Toxicium, hydrogenation hydrogen, hydrogenation power, etc.
- the above reaction can be carried out in a suitable diluent, and any diluent that can be used at that time may be one that does not itself inhibit the reaction.
- pentane, hexane, or cyclohexane Aliphatic or aromatic hydrocarbons such as xane, petroleum ether, rig mouth, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, etc., ethyl ether Ethers such as methylethyl ether, isopropyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane, etc., nitriles such as acetonitrile, propionitrile, acrylonitrile, methanol, ethanol, isopropanol, n-butanol, Alcohols such as ethylene glycol, Examples thereof include acid amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone; sulfoxides such as dimethyl
- the above reaction can be carried out within a substantially wide temperature range, but is generally from about 130 ° C to about 150 ° C; preferably from about 0 ° C to about 130 ° C. Temperatures between are preferred.
- the above reaction is preferably carried out under normal pressure, but may be carried out under increased or reduced pressure in some cases.
- the reaction can be carried out, for example, in ethanol as a diluent using 1 to 1.5 mol of the compound of the general formula (IX) per 1 mol of the compound of the general formula (VIII).
- reaction formula (2) As a raw material, for example, when using trifluoromethyl sulfonic acid 4-[(4-chloro-phenyl) -hydrazonomethyl] -phenyl ester and N-ethyloxymoyl chloride, the following reaction formula (2) is used. Is represented. Reaction formula (2)
- Table 6 shows examples of compound (X) that can be used as a raw material in the above production method.
- Compound (X) can be used in a free form or in the form of a salt.
- an appropriate base can be used as a deoxidizing agent. Examples thereof include pyridine, triethylamine, potassium carbonate, sodium bicarbonate, sodium carbonate, sodium bicarbonate, hydroxylase, sodium hydroxide, sodium methylate, sodium methylate, sodium methylate, potassium potassium sulphate, hydrogen hydrogen Sodium hydride, potassium hydride and the like.
- Compound (XI) can be easily produced, for example, according to the method described in J. Org. Chem., 48, p411-11-4113 (1983). In the above reaction, if necessary, a base can be used.
- the base that can be used is the same as the base that can be used in Production Method A described above.
- the above reaction can be carried out in a suitable diluent
- the agent may be any agent as long as it does not inhibit the reaction itself.
- esters such as ethyl acetate and the like can be mentioned.
- the above reaction can be carried out in a substantially wide temperature range, but is generally between about 130 ° C. and about 150 ° C., preferably between 0 ° C. and about 100 ° C. Temperature is good.
- the above reaction is preferably carried out under normal pressure, but may be carried out under increased or reduced pressure in some cases.
- 1 to 1.5 mol of the compound of the general formula (XI) is used per 1 mol of the compound of the general formula (X), and the reaction is carried out in a diluent, for example, tetrahydrofuran, to obtain the target compound. You can get it.
- examples of the compound of the general formula (XII) that can be used when a substituent is introduced into R 3 of the raw material of the general formula (I) in which R 3 is hydrogen include, for example, methyl iodide, And alkyl halides such as methyl bromide.
- examples of the compound of the general formula (XIII) include alkyl sulfates such as dimethyl sulfate and getyl sulfate.
- the compounds of the general formulas (XII) and (II) are known compounds and can be easily produced and obtained.
- a base can be used if necessary.
- the base that can be used is the same as the base that can be used in the above-mentioned Production Method A.
- the above reaction can be carried out in a suitable diluent, and any diluent that can be used at that time may be any as long as it does not inhibit the reaction itself.
- the diluents listed in B can be used.
- the above reaction can be carried out within a substantially wide range, but is generally carried out at a temperature between about ⁇ 30 ° C. and about 150 ° C., preferably between 0 ° C. and about 100 ° C. Is preferred.
- the above reaction is preferably carried out under normal pressure, but may be carried out under increased or reduced pressure in some cases.
- 1 to 4 mol of the compound of the general formula (XII) or ( ⁇ ⁇ ) is used per 1 mol of the compound of the general formula (I), and as a diluent, for example, N, N—
- the target compound can be obtained by carrying out the reaction in dimethylformamide.
- the substituent can be introduced into R 3 , R 4 , and R 5 in one to three steps.
- the hydrazine oxoacetoamide derivative represented by the general formula (I) of the present invention or a salt thereof has a stronger insecticidal action than conventional insecticides.
- the hydrazine oxoacetoamide derivative represented by the formula (I) or a salt thereof according to the present invention is effective against various harmful insects at an extremely low drug concentration.
- the pests include lepidoptera, scarab beetles such as sugar beetles, white cabbage butterfly, moth moths, mosquitoes, leaf snails, and beetles; Agricultural and horticultural pests, powers, flies, cockroaches, fleas, such as Hemiptera, such as white lice, aphids, and scale insects, and Thrips palmi, such as Thrips palmi, Thrips palmi Sanitary pests such as lice, lice, storage pests, clothing, house pests, root-knot nematodes, plant parasitic nematodes such as black-spotted nematodes, Namihadani, Nisenamihadani, Kanzadahadani, Citrus spidermite It is effective against plant parasitic mites such as.
- Lepidoptera which is effective for Lotus apex, Spodoptera and Konaga. It is also effective against soil pests. Examples of such soil pests include, for example, slugs, gastropods such as snails, and isopods such as duck beetles and scabies. Furthermore, it is also effective against pests such as dicophor and organophosphate-resistant plant parasitic mites, organophosphate-resistant aphids, and house flies.
- the hydrazine oxoacetoamide derivative or a salt thereof of the present invention has a remarkable insecticidal effect on the above-mentioned pests that damage paddy crops, field crops, fruit trees, vegetables, other crops, flowers and the like.
- paddy fields, fields, fruit trees, vegetables, other crops, paddy water such as flowers, foliage or soil.
- the hydrazine oxoacetoamide derivative or a salt thereof of the present invention differs depending on the target crop, the method of use, the formulation form, the application rate, and the like, and cannot be unconditionally specified. For example, it is suitable to be used in an amount of 0.1 to 100 ppm, preferably 1 to 200 ppm.
- the hydrazine oxoacetamide derivative of the present invention or a salt thereof can be prepared in a usual pharmaceutical form. It can be formulated into T / JP99 / 70.
- Such formulations include, for example, powders, solid carriers, solvents, surfactants, and other auxiliaries for formulation, which can be used as emulsions, aqueous solutions, microemulsions, wettable powders, aqueous or oily It can be formulated into suspensions, wettable powders, aqueous solvents, microcapsules and the like.
- These preparations contain the hydrazine oxoacetamide derivative of the present invention or a salt thereof as an active ingredient in an amount of, for example, 0.002 to 80% by weight, preferably 0.01 to 70% by weight. Is appropriate.
- solid carrier examples include kaolin clay, Atsushi Palgit clay, bentonite, acid clay, virofluorite, talc, diatomaceous earth, calcite, walnut shell powder, urine, ammonium sulfate, synthetic hydrous silicic acid, and the like.
- Solvents include xylene, naphthas, methylnaphthylene, paraffins, aromatic and aliphatic hydrocarbons such as machine oil, isopropanol, butanol, propylene glycol, ethylene glycol, cellosolve, sorbitol, etc. Alcohols, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, N, N-dimethylformamide, N-methylpyrrolidone, acetonitrile, water, etc. Is mentioned.
- surfactants used for emulsification, dispersion, wetting, etc. include, for example, lignin sulfonate, alkyl naphthylene sulfonate, naphthylene sulfonate formaldehyde condensate, alkyl sulfate ester, alkyl sulfate Sulfonate, alkylaryl sulfonate, dialkyl sulfosuccinate, polyoxyethylene alkylaryl ether sulfate or sulfonic acid or phosphate, polyoxyalkylene alkyl ether sulfate or phosphoric acid or sulfonate, polyoxyethylene styrenated and base
- Anionic surfactants such as phosphoric acid or sulfate esters of unzylated phenyl ether, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene ⁇ -fatty ester, polyoxy Noni
- a hydrating agent may be a hydrazine oxoacetamide derivative of the present invention or a salt thereof, for example, about 5 to 50 parts by weight, an anionic surfactant 2 to 5 parts by weight, It is prepared by mixing and pulverizing the whole with a solid carrier in an amount sufficient to make it 100 parts by weight.
- the powder is a mineral powder selected from the hydrazine oxoacetamide derivative of the present invention or a salt thereof, for example, 0.1 to 10 parts by weight, a lubricant 0.1 to 0.5 part by weight, and a solid carrier. Can be prepared by mixing.
- the emulsion contains the hydrazine oxoacetamide derivative of the present invention or a salt thereof, for example, 1 to 70 parts by weight, a nonionic surfactant 5 to 15 parts by weight, an anionic surfactant ⁇ to 10 parts by weight. It can be prepared by mixing with an inert pharmaceutically acceptable liquid diluent in an amount sufficient to make the whole 100 parts by weight.
- the aqueous suspension contains the hydrazine oxoacetoamide derivative of the present invention or a salt thereof, for example, 5 to 50 parts by weight, 1 to 5 parts by weight of a nonionic surfactant or anionic surfactant, and After mixing with water in an amount sufficient to make the whole 100 parts by weight and wet-milling until the particle size becomes 0.1 to 3; im, preferably 0.5 to 2 / m, the thickener 0.1 To 1 part by weight or the like.
- the water dispersible granule is a finely divided hydrazine oxoacetamide derivative of the present invention or a salt thereof, for example, 5 to 50 parts by weight, an inorganic salt selected from a solid carrier and / or mineral fine powder 90 Up to 40 parts by weight, binder 0.1 to 5 parts by weight, surfactant 5 to 10 parts by weight It is a granule composed of parts by volume, etc., which disintegrates and disperses rapidly when administered in water.
- the hydrazine oxoacetoamide derivative of the present invention or a salt thereof may be used, if necessary, with other pesticides such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, and herbicides. It can also be used in combination with or in combination with plant growth regulators, etc., and is expected to achieve even better effects.
- pesticides such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, and herbicides. It can also be used in combination with or in combination with plant growth regulators, etc., and is expected to achieve even better effects.
- Examples of such active compounds such as insecticides, acaricides, and nematicides include 0- (4-bromo-2-chlorophenyl) 0-ethyl S-propyl phosphoro thioate (generic name: profenophos) , 0- (2,2-dichlorovinyl) 0,0-dimethylphosphate (generic name: dichlorvos), 0-ethyl 0- [3-methyl-1- (methylthio) phenyl] N-isopropylphosphoramidate
- Organometallic compounds such as bis [tris (2-methyl-1-phenylpropyl) tin] oxide (generic name: fenbutin oxide);
- Pyridazinone-based compounds such as 2-t-butyl-5- (4-t-butylbenzylthio) -4 monocyclo-3 (2H) -pyridazinone (generic name: pyridaben); t-butyl 4-[( 1,3-dimethyl-5-phenoxypyrazol-1-yl) methyleneaminooxymethyl] benzolate (generic name: fenpyroxime); 1- (6-chloro-1-3-pyridylmethyl) 1-N-Troimidazolidin-1 2-Ilidenamine (generic name: imidacloprid), 1- [N- (6-chloro-3-1-pyridylmethyl) 1-N-ethylamino 1-methylamino-2-nitroethylene (European publication No. 302389), 2-methylamino-12- [N-methyl-1-N- (6-methyl-1-3-pyridylmethyl) amino] 1-1-nitroethylene
- 5-thiadiazine-1-one (generic name: buprofezin), trans-one (4-chlorophenyl) 1-N-cyclohexyl 4-methyl-2-oxothiazolidinone 1-3-carboxamide (generic name: hexthiazox), N-methylbis (2,4-xylyliminomethyl) amine (generic name: amitraz), ⁇ -(4-chloro-one- ⁇ -tolyl) ⁇ , ⁇ -dimethylformamidine (generic name: chlordimeform), ( Compounds such as 4- (ethoxyphenyl) -1- [3- (4-fluoro-3-phenoxyphenyl) propyl] (dimethyl) silane (general name: silafluofen); and the like. Furthermore, it can be mixed or used in combination with microbiocides, pesticides such as insect pathogen virus agents, and antibiotics such as avermectin and milbemycin.
- Examples of the active ingredient compound of the fungicide include 2-anilino-4-methyl
- Pyrimidinamine-based compounds such as 6- (1-Provinyl) pyrimidine (generic name: mepanipyrim), 4,6-dimethyi ⁇ -phenyiru 2-pyrimidinamine (generic name: pyrimesanil);
- Quinoxaline-based compounds such as quinoxaline-2-one (generic name: quinomethionate); polymer of manganese ethylene bis (dithiocarbamate) (generic name: Maneb), a polymer of zinc ethylene bis (dithiocarbamate) (general name: zineb), a complex compound of zinc (zinc) and manganez ethylene bis (dithiocarbamate) (mannep) (general name: manzeb), Dizinc bis (dimethyl dithiocarbamate) Ethylene bis (dithiocarbamate) (generic name: polycarbamate), zinc propylene bis A dithiocarbamate compound such as a polymer (generic name: provineb) of dithiocarbamate;
- Methyl N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-arananate (general name: metalaxyl), 2-methoxy-N- (2-oxo-1,3-oxazolidine-13-) 2), 6'-Xylidide (generic name: oxaxixyl), (I) Ichiichi 2-chloro-1-N- (2,6-xylylacetoamide) 1-butyrolactone (generic name) : Off-race), methyl N-phenylacetyl-N- (2,6-xylyl) -DL-alaninate (general name: benalaxyl), methyl N- (2-furoyl) -N- (2,6-xylyl) 1) DL-ara2nate (general name: flalaxil), (Sat) 1-Hiichi N- (3-chloroporous phenyl) cyclopropanecarboxamide]
- N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsul Sulfenic acid-based compounds such as fuamide (generic name: diclofluanid); copper such as cupric hydroxide (generic name: cupric hydroxide) and kappa-18-quinolinolate (generic name: organic copper) Compound;
- Isoxazole-based compounds such as 5-methylisoxazol-3-ol (generic name: hydroxy isoxazole); aluminum tris (ethyl phosphonet) (generic name: fosetyl aluminum), 0-2, 6- Dichloro-p-tolyl mono 0,0-dimethyl phosphorothioate (generic name: phosphorous methyl phosphate), S-benzyl 0,0-diisopropyl phosphorothioate, 0-ethyl S, S-diphenyl Organophosphorus compounds such as phosphorodithioate and aluminum ethylhydrogen phosphonate;
- N- (Trichloromethylthio) cyclohex-1-ene-1,2-dicarboximide (generic name: captan), N- (1,1,2,2-tetrachloroethylthio) cyclohexyl N-halogenothioalkyl-based compounds such as 1,1-dicarboxymide (general name: capphol) and N- (trichloromethylthio) phthalimide (general name: phthalate);
- Benzanilide-based compounds such as a, a, 1-trifluoro-3'-isopropoxy 1-toluanilide (generic name: flutolanil) and 3'-isopropoxy-o-toluanilide (generic name: mepronil);
- N, N '-Piperazine-based compound such as [piperazine-1,4-diylbis [(trichloromethyl) methylene] diformamide (generic name: triforine);', 4 'dichloro-2- (3-pyridyl) acetophenone 0 Pyridine compounds such as methyloxime (generic name: pyriphenox);
- Trifeniltin hydroxide (generic name: fentin hydroxide): an organic tin-based compound such as triphenylnitine acetate (generic name: fentin acetate);
- Urea compounds such as 1- (4-cyclopentyl) 1-1-cyclopentyl-3-phenylperyla (generic name: peniculone);
- the optional components described above may be mixed with or used in combination with the hydrazine oxoacetamide derivative of the present invention or a salt thereof.
- the mixing weight ratio with the optional component is generally from 1: 300 to 300: 1, preferably from 1: 100 to 100: 1.
- Trifluoromethanesulfonic acid 4-[(4-cyclophenyl)-(ethylamino-oxalyl-hydrazono) -methyl] -phenyl ester (compounds 1-5) 1.44 g, potassium carbonate 0.55 and 0] 0 ⁇ 0.46 g of methyl iodide was added to 9 ml of the mixture, and the mixture was stirred at room temperature for 20 hours. The reaction solution was poured into dilute hydrochloric acid and extracted with ethyl acetate. The separated organic layer was washed with water and then with a saturated saline solution, and dried over magnesium sulfate.
- Trifluorenesulfonic acid 4-[((4-chlorophenyl)-(dimethylamino-minoxalyl-hydrazono) -methyl]]-phenyl ester (compound 1-133) 0.6 g, potassium carbonate 0.24 and 01 ⁇ 1? 0.22 g of methyl iodide was added to 5 ml of the mixture, and the mixture was stirred at room temperature for 20 hours. The reaction solution was poured into diluted hydrochloric acid and extracted with ethyl acetate. The separated organic layer was washed with water and then with saturated saline, and then washed with sulfuric acid. Dried in gusset.
- Table 5 below shows examples of physical properties of the compounds obtained in the same manner as in Production Examples 1 to 5 together with the physical properties of the above compounds.
- Compound A-2 or 14 finely pulverized to a particle size of 5 m with a hammer mill 25 parts, polyethylene ethylene styrenated phenyl ether sulfate ammonium salt 3 parts, water 62 parts 2 and a small amount of defoaming The mixture was mixed and pulverized until the average particle size reached 2 m. After that, 10 parts of a pre-prepared solution consisting of 2 parts of Zhang Yun Gum, 1 part of preservative, 50 parts of ethylene glycol and 47 parts of water was mixed to obtain a suspension.
- Formulation Example 4 Water dispersible granules
- an emulsion was prepared using the compounds of the present invention shown below.
- the resulting emulsion was diluted with water so that the compound of the present invention was 50 ppm, 5 ppm and 0.5 ppm, respectively, to prepare a water dilution.
- the obtained water diluted solution is sprayed on Chinese cabbage leaves at the 3-4 leaf stage, air-dried, and then placed in a plastic container of 21 cm in width X 13 cm in width X 3 cm in depth. 10 larvae of 3rd instar larvae of Spodoptera litura were released, covered and left to stand in a constant temperature room at 26 ° C. The number of live and dead insects after 48 hours was investigated to determine the mortality. Calculated.
- Emulsions of each concentration produced in the same manner as in Biological Test Example 1 were sprayed on Chinese cabbage leaves at the 3-4 leaf stage. After air drying, place in a plastic container with a 9 cm inner diameter and 6.5 cm depth, and release 10 third-instar larvae of Plutella xylosteUa into the plastic container. They were left in a constant temperature room, and the number of live and dead insects after 48 hours was investigated, and the mortality was calculated. The results are shown in Table 7 below, together with the results obtained when the comparative product was used. Table 7
- an emulsion was prepared using the compounds of the present invention shown below.
- the obtained emulsion was diluted with water so that the compound of the present invention had a predetermined concentration, to prepare a water dilution.
- the obtained water diluted solution is sprayed on the leaves of the cucumber at the 2-3 leaf stage, air-dried, and then placed in a plastic container having an inner diameter of 9 cm x a depth of 6.5 cm.
- Ten third-instar larvae were released, capped, and allowed to stand in a constant temperature room at 26 ° C.
- the number of live and dead animals after 48 hours was investigated, and the mortality was calculated.
- the results are shown in Table 9 below together with the results when the comparative compound was used. Table 9
- the compound of the present invention was suspended at a predetermined concentration in a 0.5% carboxymethylcellulose aqueous solution, and a 6-week-old SIc: ICR mouse (SPF) (body weight: 29.5 to 34.4 g) was fasted for 3 hours.
- SIc ICR mouse
- Each animal was forcibly administered 1 ml per 100 g body weight to the stomach. After administration, food and water were given, and the animals were kept in cages. After the administration, the observation period was 7 days. The animals were observed for life and death, general condition, and changes in body weight, and a pathological anatomy was performed at the end of the observation (2 animals per group).
- Compound No. 15 did not show any death or abnormal condition at a concentration of 300 rag / k, a steady increase in body weight, and no abnormalities due to anatomical findings at the end of observation. . It can be seen that the compound of the present invention has excellent insecticidal activity, particularly at a low concentration, and has excellent safety for animals as compared with conventionally known hydrazine oxoacetoamide-related compounds. .
Description
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99947967A EP1123920A4 (en) | 1998-10-19 | 1999-10-19 | HYDRAZINO-OXOACETAMIDE DERIVATIVES AND INSECTICIDES |
AU61249/99A AU6124999A (en) | 1998-10-19 | 1999-10-19 | Hydrazinooxoacetamide derivatives and insecticide |
JP2000577150A JP4331408B2 (ja) | 1998-10-19 | 1999-10-19 | ヒドラジンオキソアセトアミド誘導体及び殺虫剤 |
US09/837,656 US6399659B2 (en) | 1998-10-19 | 2001-04-19 | Hydrazine oxoacetamide derivative and insecticide |
US10/158,916 US20030087958A1 (en) | 1998-10-19 | 2002-06-03 | Hydrazine oxoacetamide derivative and insecticide |
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Application Number | Priority Date | Filing Date | Title |
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JP10/297240 | 1998-10-19 | ||
JP29724098 | 1998-10-19 |
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US09/837,656 Continuation US6399659B2 (en) | 1998-10-19 | 2001-04-19 | Hydrazine oxoacetamide derivative and insecticide |
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WO2000023422A1 true WO2000023422A1 (fr) | 2000-04-27 |
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PCT/JP1999/005760 WO2000023422A1 (fr) | 1998-10-19 | 1999-10-19 | Derives d'hydrazino-oxoacetamide et insecticide |
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US (2) | US6399659B2 (ja) |
EP (1) | EP1123920A4 (ja) |
JP (1) | JP4331408B2 (ja) |
AU (1) | AU6124999A (ja) |
TW (1) | TW479053B (ja) |
WO (1) | WO2000023422A1 (ja) |
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US6545219B1 (en) * | 2000-04-24 | 2003-04-08 | Tyco Electronics Corporation | Wrap-around cable sleeves having an expandable body portion and methods of making same |
TWI332943B (en) * | 2001-07-10 | 2010-11-11 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
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JPH0841013A (ja) * | 1994-01-24 | 1996-02-13 | Sumitomo Chem Co Ltd | ヒドラゾン化合物およびそれを有効成分とする殺虫剤 |
JPH09278744A (ja) * | 1995-05-12 | 1997-10-28 | Nippon Bayeragrochem Kk | ベンゾフエノンヒドラゾン誘導体及び殺虫剤 |
DE19831803A1 (de) * | 1997-07-18 | 1999-04-01 | Novartis Ag | Organische Hydrazinverbindungen |
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NZ189705A (en) * | 1978-03-01 | 1981-07-13 | Boots Co Ltd | Benzophenone-hydrazone derivatives and pesticidal compositions intermediates |
JPH1067732A (ja) * | 1996-08-27 | 1998-03-10 | Otsuka Chem Co Ltd | ヒドラゾン誘導体及び該誘導体を有効成分とする殺虫剤 |
-
1999
- 1999-10-13 TW TW088117645A patent/TW479053B/zh not_active IP Right Cessation
- 1999-10-19 EP EP99947967A patent/EP1123920A4/en not_active Withdrawn
- 1999-10-19 AU AU61249/99A patent/AU6124999A/en not_active Abandoned
- 1999-10-19 WO PCT/JP1999/005760 patent/WO2000023422A1/ja not_active Application Discontinuation
- 1999-10-19 JP JP2000577150A patent/JP4331408B2/ja not_active Expired - Fee Related
-
2001
- 2001-04-19 US US09/837,656 patent/US6399659B2/en not_active Expired - Fee Related
-
2002
- 2002-06-03 US US10/158,916 patent/US20030087958A1/en not_active Abandoned
Patent Citations (3)
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JPH0841013A (ja) * | 1994-01-24 | 1996-02-13 | Sumitomo Chem Co Ltd | ヒドラゾン化合物およびそれを有効成分とする殺虫剤 |
JPH09278744A (ja) * | 1995-05-12 | 1997-10-28 | Nippon Bayeragrochem Kk | ベンゾフエノンヒドラゾン誘導体及び殺虫剤 |
DE19831803A1 (de) * | 1997-07-18 | 1999-04-01 | Novartis Ag | Organische Hydrazinverbindungen |
Non-Patent Citations (1)
Title |
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See also references of EP1123920A4 * |
Also Published As
Publication number | Publication date |
---|---|
JP4331408B2 (ja) | 2009-09-16 |
US20010044464A1 (en) | 2001-11-22 |
US20030087958A1 (en) | 2003-05-08 |
EP1123920A1 (en) | 2001-08-16 |
EP1123920A4 (en) | 2002-06-26 |
TW479053B (en) | 2002-03-11 |
US6399659B2 (en) | 2002-06-04 |
AU6124999A (en) | 2000-05-08 |
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