专利摘要:
The present invention relates to pesticidal mixtures of chloronicotinyl pesticides of general formula (I) with one or more synergists mentioned in the description: Where R 1 represents C 1 -C 5 -alkyl, R 2 represents hydrogen or C 1 -C 5 -alkyl, or R 1 and R 2 together are —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 — or Indicates X represents an NH group, an NCH 3 group or sulfur, Y represents nitrogen or CH group, Z represents cyano or nitro.
公开号:KR19990014937A
申请号:KR1019970708283
申请日:1996-05-13
公开日:1999-02-25
发明作者:크리스토프 에르델렌;볼프강 크레머;카이-우베 브뤼겐
申请人:귄터 슈마허, 크누트 샤우에르테;바이엘 악티엔게젤샤프트;
IPC主号:
专利说明:

Pesticide
The present invention relates to pesticide compositions based on chloronicotinyl insecticides and synergists for insecticides.
Chloronicotinyl pesticides are known for example from EP-OS (European published application) 192 060.
Insecticide synergists are inhibitors of oxidase or chitochrome P450 or increase the permeability of cell membranes. Synergists are described, for example, in Chemie der Pflanzenschutz-und Sch dlingsbek mpfungsmittel Volume 7K. Naumann Chemie der Synthetischen Pyrethroid-Insektizide Springer Verlan 1981 pages 3-5.
The present invention provides a chloronicotinyl insecticide of general formula (I) and O, O-dimethyl S- (4-oxo-1, 2, 3-benzotriazine-3-methyl) dithiophosphate [M-Gusathion]; O-ethyl O- (4-bromo-2-chlorophenyl) -s- # N-propyl thiophosphate [Curacron]; 3, 5-dimethyl-4-methylthiophenyl N-methylcarbamate [Mesurol]; 4-bromo-2- (4-chlorophenyl) -2- (ethoxymethyl) -5- (trifluoromethyl) -1H-pyrrole-3-carbonitrile [AC 303,630]; O, S-dimethyl phosphoramidothioate [Tamaron]; N- [2, 6-bis (1-methylethyl) -4-phenoxyphenyl) -N '-(1, 1-dimethylethyl) -thiourea [CGA 106 630; Polo]; Abamectin; Ethyl (3-t-butyl-1-dimethylcarbamoyl-1H-1, 2, 4-triazol-5-ylthio) -acetate [Triazuron]; 6, 7, 8, 9, 10, 10-hexachloro-1, 5, 5A, 6, 9, 9A-hexahydro-6, 9-methane-2, 4, 3-benzodioxathiene 3-oxide Endosulfan; Thiodan; Trans-5- (4-chlorophenyl) -N-cyclohexyl-4-methyl-2-oxo-3-thiazolidine-carboxamide [Cesar; Hexythiazox]; 3, 6-bis- (2-chlorophenyl) -1, 2, 4, 5-tetrazin [Clofentezin; Apollo; Ethyl [2- (4-phenoxyphenoxy) -ethyl] carbamate [Fenoxyxcarb; Insegar; 2- [1-methyl-2- (4-phenoxyphenoxy) ethoxy] pyridine [Pyriproxyfen; Tiger]; N-cyclopropyl-1, 3, 5-triazine-2, 4, 6-triamine [Cyromazine]; Benzoic acid [2-benzoyl-1- (1, 1-dimethyl)] hydrazide [RH 5849]; 5-amino-3-cyano-1- (2, 6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylthionopyrazole [Fipronil]; Cis- (2, 3, 5, 6-tetrafluoro-4-methylphenyl) methyl-3- (2-chloro-3, 3, 3-trifluoro-1-propenyl) -2, 2-dimethyl- Cyclopropane-carboxylate [Tefluthrin; Force]; 1, 5-bis- (2, 4-dimethylphenyl) -3-methyl-1, 3, 5-triazapenta-1, 4-dione [Amitraz]; 3, 5-dimethylbenzoic acid 1- (1, 1, -dimethylethyl) -2- (4-ethylbenzoyl) hydrazide [RH 5992]; N-[[2,5-dichloro-4- (1, 1, 2, 3, 3, 3-hexafluoropropoxy) phenyl] -aminocarbonyl] -2, 6-difluorobenzamide [Match ]; (4-ethoxyphenyl)-[3- (4-fluoro-3-phenoxyphenyl) propyl] dimethylsilane [HOE 498]; And / or (E) -4, 5-dihydro-6-methyl-4-[(3-pyridinylmethylene) amino] -1, 2, 4-triazine-3- (2H) -one [Chess] A mixture of one or more synergists selected from the group consisting of:

Where
R 1 represents C 1 -C 5 -alkyl,
R 2 represents hydrogen or C 1 -C 5 -alkyl, or
R 1 and R 2 together are —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 — or Indicates
X represents an NH group, an NCH 3 group or sulfur,
Y represents nitrogen or CH group,
Z represents cyano or nitro.
Preferred are novel mixtures of the synergists specified above with chloronicotinyl pesticides of the formula


Especially preferred are novel mixtures of the abovementioned synergists with chloronicotinyl pesticides of the formula
or
The novel active compound mixtures of chloromycotinyl insecticides with the synergists specified above can be prepared by conventional preparations, for example solutions, emulsions, suspending agents, powders, foams, pastes, granules, aerosols, natural and impregnated with active compounds. Conventional formulations such as synthetics and coating compositions for polymers and seeds, or formulations with smoke such as fumigating cartridges, fumigating cans, fumigating coils and the like, and microcapsules in ULV cold and warm mist formulations. Can be converted to
These formulations are known methods, for example using surfactants, ie emulsifiers and / or dispersants and / or foam-forming agents, to extend the active compounds into extenders, i.e. liquid solvents, pressurized liquefied gases and / or solid carriers. It is prepared by mixing with.
When water is used as the extender, for example an organic solvent can also be used as an auxiliary solvent. Liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffin, for example aliphatic hydrocarbons such as mineral oil fraction Alcohols such as butanol or glycol and ethers and esters thereof, as well as strong polar solvents such as ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, dimethylformamide and dimethyl sulfoxide, are suitable; By liquefied gas extender or carrier is meant a liquid that is gaseous at room temperature and at atmospheric pressure, for example halogenated hydrocarbons and erosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are, for example, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silica, alumina and silicates. Solid carriers for granules include, for example, pulverized natural rock such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic materials such as sawdust, coconut husks, corn cobs and tobacco stems. Granules are suitable. Emulsifiers and / or foam-forming agents include, for example, nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, aryls Sulfonates and protein hydrolysates are suitable. Suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.
Adhesives, for example, natural and synthetic polymers in the form of powders, granules or emulsions, such as carboxymethylcellulose, gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids may be used in the formulation. Can be. As other additives, mineral oil and vegetable oil may be used.
Traces such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc and coloring materials such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes You can also use nutrients.
The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.
The active compound mixtures are suitable for the control of insects, arachnids and nematodes encountered in the protection and hygiene zones of animal pests, especially agriculture, forestry, storage and materials, and good for plant resistance and warm-blooded animals. Toxic The active compound mixtures are active against all or some stages of moderately sensitive or resistant species and transformations. The pests mentioned above include the following.
Isopoda neck, for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber.
Dipopoda throat, for example Blaniulus guttulatus.
From the neck of Chilopoda, for example, Geophilus carpophagus and Scutigera spec.
From the tree of Sumphyla, for example Scutigerella immaculata.
From the order of Thysanura, for example, Lepisma saccharina.
The neck of Collembola, for example Onychiurus armatus.
From the order of the Orthoptera, for example, Blata orientalis, Periplaneta ameicana, Leucophaea maderae, Blatella germanica, Ah Keta Domestikus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Systocerca gre Schistocerca gregaria.
From the order of the dermaptera, for example Porficula auricularia.
Termite Isoptera, for example Reticulitermes spp.
Anoplura, for example Pediculus Humanus corporis, Haematopinus spp. And Linognathus spp.
Allophaga, for example Trichotectes spp. And Damaliane spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis and Tripps tabaci.
From the order of the Heteroptera, for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rodney Rhodnius prolixus and Triatoma spp.
The cicada (Homoptera), for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Apis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, hyaloptherus Hyalopterus arundinis, Macrorosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Phyloxera batrix (Macrophum avenae) Phylloxera vastrix, Pemphigus spp., Empoasca spp., Eucelis bilobatus, Nephotetics cincticeps, Recanium corni Lecanium corni, Saicetia oleea (Sai) ssetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudo Pseudococcus spp. And Psylla spp.
The order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euprotis chrysorrhoea, Lymantria spp. , Buculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Et al. Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodonia litura (Prode nia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp. , Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinnea pellionella, Hofmannophila pseudospretella, Cacoacia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiuela ambiguella), Homona magnaima and Tortrix virdana.
The order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus ), Hilotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica species spp.), Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antonomomus Species (Anthonomus spp.), Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Cethorthorcusus assimilus ssimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrasno spp., Atenagen spp. ), Lyctu spp., Meligthes aeneus, Pintin spp., Niptus hololeucus, Gibbium psylloides , Tribolium spp., Tenebrio moltor, Agriotes spp., Conoderus spp., Melonta Melontalon, Amphi Amphimallon solstitialis and Costelitra zealandica.
Hymenopera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa species ( Vespa spp.).
Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca species ( Musca spp, Fannia spp., Calaphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hippobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Taba Tabsnus spp., Tannia spp., Biboi hortulanus, Oscinella frit, Phorbia spp., Pegomia hisosiami Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.
From the tree of Siphonaptera, for example Xenopsylla cheopis and Ceratophyllus spp.
Arachnida, for example Scorpio maurus and Latrodectus mactans.
The order of the ticks Acarina, e.g., Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae Eriopis libis Eriophyes ribis, Phyllocoptruta olevora, Bophylus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp. ), Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp. , Bryobia praetiosa, Panonicus spp., And Tetranychus spp.
In plant parasitic nematodes, Pratylenchus spp., Radopholus similis, Ditylenchus dipsasi, Tylenchulus semipenetrans, Heterodera species spp.), Meloidogyne spp., Apelenchoides spp., Longidorus spp., and Trichodorus spp.
The active compounds according to the invention are prepared from commercially available formulations and mixtures of these with other active compounds such as insecticides, attractants, fungicides, acaricides, nematicides, fungicides, growth-modulating substances or herbicides. May exist in the form of use. Pesticides include, for example, phosphates, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylurea, materials produced by microorganisms, and the like.
The active compound content of the use forms prepared from commercially available formulations can vary within considerable ranges. The concentration of the active compound of the use form is 0.0000001 to 95% by weight, preferably 0.0001 to 1% by weight.
The compound is used in a conventional manner suitable for the use form.
In the examples that follow, imidacloprids of the following structural formula are used as pesticidal active compounds from the group of chloronicotinyl pesticides:

Example of use
Example A
Phaedon Larva Test
Solvent: Dimethylformamide 7 parts by weight
Emulsifier: alkylaryl polyglycol ether 1 part by weight
1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
Cabbage mouth (Brasica oleracea) is treated by immersion in the active compound formulation of the desired concentration, and infected with mustard beetle larvae (Peadon cocleariae) while the leaves are moist.
After a certain period of time, plants have beetles (Phaedon cochleariae). In each case, the percentage of relief is determined after 7 days. 100% means that all the beetle larvae have been killed; 0% means that the beetle larva is not killed at all.
A 0.02% synergist was mixed in each case to imidacloprid at a particular test concentration. Synergy in this test is exhibited, for example, by the following mixture.
TABLE A
(Plant pests)
Phaedon Larva Test

Example B
Flutella test (BLT resistance)
Solvent: Dimethylformamide 7 parts by weight
Emulsifier: alkylaryl polyglycol ether 1 part by weight
1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
Cabbage leaves (Brasica oleracea) are treated by immersing the active compound in the desired concentration in the formulation and infected with cabbage moth (Flutella maculenis, BLT resistant) caterpillars while the leaves are moist.
After a certain period of time, the percentage of relief is determined. 100% means that all caterpillars have been killed; 0% means that the caterpillar was not killed at all.
A 0.02% synergist is mixed in each case to imidacloprid at a particular test concentration. Synergy in this test is exhibited, for example, by the following mixture.
TABLE B
(Plant pests)
Flutella test (resistant)

Example B
Spodovterra Exam
Solvent: Dimethylformamide 7 parts by weight
Emulsifier: alkylaryl polyglycol ether 1 part by weight
1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
Cabbage leaves (Brasica oleracea) are treated by dipping into active compound preparations of the desired concentration and infected with caterpillar (Spodoptera frugiperda) caterpillars while the leaves are moist.
After a certain period of time, the percentage of relief is determined. 100% means that all caterpillars have been killed; 0% means that the caterpillar was not killed at all.
A 0.02% synergist is mixed in each case with imidacloprid at a particular test concentration. Synergy in this test is exhibited, for example, by the following mixture.
TABLE C
(Plant pests)
Spodovtera Fringeferda

Example D
Myzus Exam
Solvent: Dimethylformamide 7 parts by weight
Emulsifier: alkylaryl polyglycol ether 1 part by weight
1 part by weight of the active compound was mixed with the specified amount of solvent and the specified amount of emulsifier, and the concentrate was diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
Cabbage leaves (Brasica oleracea) heavily infected with peach mite (Myzus persicae) are immersed in an active compound detergent of the desired concentration.
After a certain period of time, the percentage of relief is determined. 100% means that all ticks have been killed; 0% means that the tick is not killed at all.
TABLE D
(Plant pests)
Miss Juice Test

权利要求:
Claims (6)
[1" claim-type="Currently amended] With chloronicotinyl insecticide of general formula (I)
O, O-dimethyl S- (4-oxo-1, 2, 3-benzotriazine-3-methyl) dithiophosphate [M-Gusathion]; O-ethyl O- (4-bromo-2-chlorophenyl) -s- # N-propyl thiophosphate [Curacron]; 3, 5-dimethyl-4-methylthiophenyl N-methylcarbamate [Mesurol]; 4-bromo-2- (4-chlorophenyl) -2- (ethoxymethyl) -5- (trifluoromethyl) -1H-pyrrole-3-carbonitrile [AC 303,630]; O, S-dimethyl phosphoramidothioate [Tamaron]; N- [2, 6-bis (1-methylethyl) -4-phenoxyphenyl) -N '-(1, 1-dimethylethyl) -thiourea [CGA 106 630; Polo]; Abamectin; Ethyl (3-t-butyl-1-dimethylcarbamoyl-1H-1, 2, 4-triazol-5-ylthio) -acetate [Triazuron]; 6, 7, 8, 9, 10, 10-hexachloro-1, 5, 5A, 6, 9, 9A-hexahydro-6, 9-methane-2, 4, 3-benzodioxathiene 3-oxide Endosulfan; Thiodan; Trans-5- (4-chlorophenyl) -N-cyclohexyl-4-methyl-2-oxo-3-thiazolidine-carboxamide [Cesar; Hexythiazox]; 3, 6-bis- (2-chlorophenyl) -1, 2, 3, 5-tetrazin [Clofentezin; Apollo; Ethyl [2- (4-phenoxyphenoxy) -ethyl] carbamate [Fenoxyxcarb; Insegar; 2- [1-methyl-2- (4-phenoxyphenoxy) ethoxy] pyridine [Pyriproxyfen; Tiger]; N-cyclopropyl-1, 3, 5-triazine-2, 4, 6-triamine [Cyromazine]; Benzoic acid [2-benzoyl-1- (1, 1-dimethyl)] hydrazide [RH 5849]; 5-amino-3-cyano-1- (2, 6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylthionopyrazole [Fipronil]; Cis- (2, 3, 5, 6-tetrafluoro-4-methylphenyl) methyl-3- (2-chloro-3, 3, 3-trifluoro-1-propenyl) -2, 2-dimethyl- Cyclopropane-carboxylate [Tefluthrin; Force]; 1, 5-bis- (2, 4-dimethylphenyl) -3-methyl-1, 3, 5-triazapenta-1, 4-dione [Amitraz]; 3, 5-dimethylbenzoic acid 1- (1, 1, -dimethylethyl) -2- (4-ethylbenzoyl) hydrazide [RH 5992]; N-[[2,5-dichloro-4- (1, 1, 2, 3, 3, 3-hexafluoropropoxy) phenyl] -aminocarbonyl] -2, 6-difluorobenzamide [Match ]; (4-ethoxyphenyl)-[3- (4-fluoro-3-phenoxyphenyl) propyl] dimethylsilane [HOE 498]; And (E) -4, 5-dihydro-6-methyl-4-[(3-pyridinylmethylene) amino] -1, 2, 4-triazine-3- (2H) -one [Chess] Insecticidal composition of one or more synergists selected from the group consisting of:

Where
R 1 represents C 1 -C 5 -alkyl,
R 2 represents hydrogen or C 1 -C 5 -alkyl, or
R 1 and R 2 together are —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 — or Indicates
X represents an NH group, an NCH 3 group or sulfur,
Y represents nitrogen or CH group,
Z represents cyano or nitro.
[2" claim-type="Currently amended] The insecticidal composition of claim 1, wherein the chloronicotinyl insecticide and the one or more synergists have the structure


[3" claim-type="Currently amended] The insecticidal composition of claim 1, wherein the chloronicotinyl pesticide and one or more synergists and pesticidal compositions of the formula
or
[4" claim-type="Currently amended] A process for preparing a pesticidal composition of a chloronicotinyl insecticide according to claim 1 and one or more synergists, characterized in that the active compound is mixed with an extender, optionally using a surfactant.
[5" claim-type="Currently amended] The pesticidal composition of claim 1 comprising from 0.1 to 95% by weight of the active compound mixture.
[6" claim-type="Currently amended] Use of an insecticidal active compound composition according to claim 1 useful for controlling insects, arachnids of arachnids and nematodes.
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引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题
法律状态:
1995-05-24|Priority to DE19519007.6
1995-05-24|Priority to DE19519007A
1996-05-13|Application filed by 귄터 슈마허, 크누트 샤우에르테, 바이엘 악티엔게젤샤프트
1996-05-13|Priority to PCT/EP1996/002039
1999-02-25|Publication of KR19990014937A
2004-06-16|Application granted
2004-06-16|Publication of KR100420161B1
2013-09-11|First worldwide family litigation filed
优先权:
申请号 | 申请日 | 专利标题
DE19519007.6|1995-05-24|
DE19519007A|DE19519007A1|1995-05-24|1995-05-24|Insecticidal agents|
PCT/EP1996/002039|WO1996037105A1|1995-05-24|1996-05-13|Insecticides|
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