DE3620021A1 - Aldoxime carbamate, process for its preparation, and its use for controlling pests - Google Patents

Abstract

Oxime carbamate of the formula I <IMAGE> a process for the preparation of the oxime carbamate, and the use of the oxime carbamate for controlling pests.

Description

The present invention relates to an oxime carbamate, process for the same Manufacture, pesticides that this oxime carbamate as Contain active ingredient, as well as a method for controlling pests with this active ingredient.

Aldoximcarbamate, which is derived from substitution products of 2,2-dimethylpropionaldehyde (Pivalaldehyde) are derived from DE-AS 20 15 527, DE-AS 21 11 156 and US Patent 38 35 174 known. they are suitable for controlling insects and mites. Your impact is however, not always completely satisfactory, especially at low concentrations.

It has been found that the oxime carbamate of the formula I Insecticidal, acaricidal and nematicidal are very effective and are superior to known active ingredients with a similar structure or direction of action.

The oxime carbamate of formula I z. B. by reacting 3-chloro-2,2- Dimethylpropionaldoxim be obtained with methyl isocyanate. she will expediently in the presence of a solvent or diluent made and runs i. a. in the presence of a moderate catalyst Temperature above 0 ° C, e.g. B. from 20 to 50 ° C.

Examples of suitable solvents or diluents are:

aliphatic and aromatic, optionally chlorinated hydrocarbons, such as benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene; Ethers such as diethyl and di-n butyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane; Ketones, for example acetone, methyl ethyl ketone, methyl isopropyl ketone; further Nitriles such as acetonitrile and propionitrile. Mixtures of these substances can be used as solvents or diluents.  

Suitable catalysts are, for example, tertiary bases, such as triethylamine, Pyridine and 1,4-diazabicyclo [2.2.2] octane; further organic tin Compounds such as dibutyltin diacetate.

The reaction is preferably carried out with an excess of methyl isocyanate and wins the compound of the invention in the usual way.

Another suitable method for obtaining the oxime carbamate (I) is the reaction of 3-chloro-2,2-dimethylpropionaldoxim with methylcarbamic acid chloride in the presence of an inorganic or organic acid acceptor or, what on the gradual implementation of the aldoxime with the Precursors of the methyl isocyanate results in the reaction of 3-chloro 2,2-dimethylpropionaldoxime with phosgene and then with methylamine, also in the presence of a diluent and an acid-binding Means.

The chloropivalaldehyde required for the conversion to the oxime is known (see J. Org. Chem. 43, 1285 to 1286 (1978); J. Am. Chem. Soc. 105, 5665-5675 (1983)).

Production of the preliminary product

63.5 g of powdered sodium hydroxide are dissolved in a mixture of 155 ml of water and 650 ml of ethanol. 113.5 g of hydroxylamine hydrochloride in 70 ml of water are added with cooling, the precipitated sodium chloride is filtered off with suction and 166.5 g of chloropivalaldehyde are added with stirring at a maximum of 30 ° C. The mixture is stirred for 12 hours at room temperature and poured into water, saturated with sodium chloride and extracted five times with 150 ml of ether. The extract is dried over sodium sulfate. After the solvent has been stripped off, a yellow oil remains, which i. V. is distilled. 120 g of 2-methyl-2 (chloromethyl) propionaldoxime are obtained as a colorless oil with a boiling range at a pressure of 5 mbar of 63-65 ° C.
Yield: 64% of the calculated amount.
Infrared absorptions (cm ^-1 ): 1382, 1367, 1296, 988, 946, 889.

Manufacturing example:

A solution of 7.3 g of 3-chloro-2,2-dimethylpropionaldoxime in 50 ml of dry diethyl ether is mixed with three drops of dibutyltin diacetate, 4.6 g of methyl isocyanate are added with stirring, the mixture is heated under reflux for 5 hours and the solvent is removed: it is obtained an almost colorless oil that crystallizes after some time. After recrystallization from pentane / methyl tert-butyl ether (3: 1), 10.1 g (97% of the arithmetically possible amount) of 3-chloro-2,2-dimethyl-propanal- (N'-methylcarbamoyl) - oxime are obtained as a white powder.
Mp: 59-61 ° C
Characteristic infrared absorptions (cm ^-1 ):
1498, 1231, 1105, 961
C ₇ H ₁₃ ClN ₂ O ₂ (192.5)
calc .: C 43.6 H 6.8 N 14.5
found: C 43.5 H 7.0 N 14.8

The compound of formula I according to the invention is suitable for pests effectively combat the class of insects, arachnids and nematodes. You can in crop protection as well as on hygiene, stored product protection and Veterinary sector can be used as a pesticide.

Harmful insects belong to the order of the butterflies (Lepidoptera) for example Plutella maculipennis (cockroach), Leucoptera coffeella (coffee moth), Hyponomeuta malinellus (apple tree moth), Argyresthia conjugella (apple moth), Sitotroga cerealella (Grain moth), Phthorimaea operculella (potato moth), Capua reticulana (Apple peeler), Sparganothis pilleriana (springworm), Cacoecia murinana (pine shoots), Tortrix viridana (oak rolls), Clysia ambiguella (hay and sour worm), Evetria buoliana (pine shooter), Polychrosis botrana (crossed grape wrapper) Cydia pomonella (fruit-made), Laspeyresia molesta (peach shoots), Laspeyresia funebrana (plum wrapper), Ostrinia nubilalis (European corn borer), Loxostege sticticalis (European beet borer), Ephestia kuehniella (Flour moth), Chilo suppressalis (rice stalk borer), Galleria mellonella (Wax moth), Malacosoma neustria (ring spinner), Dendrolimus pini (Pine moth), Thaumatopoea pityocampa (pine processionary moth), Phalera bucephala (moonspot), Cheimatobia brumata (little frost tree), Hibernia defoliaria (large frost tree), Bupalus piniarius (Pine tensioner), Hyphantria cunea (white bear spinner), Agrotis segetum (Winter seed owl), Agrotis ypsilon (Ypsiloneule), Barathra brassicae (Coal owl), cirphis unipuncta (army worm), prodenia litura (cotton caterpillar), Laphygma exigua (beet armyworm), Panolis flammea (forleule), Earias insulana (cotton capsule worm), Plusia gamma (Gammaeule), Alabama argillacea (cotton leaf worm), Lymantria dispar (sponge moth), Lymantria monacha (nun), Pieris brassicae (cabbage white butterfly), Aporia crataegi (White tree);

from the order of the beetles (Coleoptera), for example, Blitophaga undata (Black beet beetle), Melanotus communis (wireworm), Limonius californicus (wireworm), Agriotes lineatus (seedling beetle), Agriotes obscurus (humus click beetle), Agrilus sinuatus (pear beetle), Meligethes aeneus (rapeseed beetle), Atomaria linearis (moss button beetle), Epilachna varivestris (Mexican bean beetle), Phyllopertha horticola (June beetle), Popillia japonica (Japanese beetle), Melolontha melolontha (Cockchafer), Melolontha hippocastani (cockchafer), amphimallus solstitialis (fallow beetle), Crioceris asparagi (asparagus chicken), Lema melanopus (cereal), Leptinotarsa decemlineata (Colorado beetle), Phaedon cochleariae (horseradish leaf beetle), Phyllotreta nemorum (Kohlerdfloh), Chaetocnema tibialis (beet flea beetle), Phylloides chrysocephala  (Rape flea beetle), Diabrotica 12-punctata (southern corn rootworm), Cassida nebulosa (misty tortoise beetle), Bruchus lentis (lenticular beetle), Bruchus rufimanus (horse bean beetle), Bruchus pisorum (pea beetle), Sitona lineatus (lined leaf beetle). Otiorrhynchus sulcatus (grooved ragweed), Otiorrhynchus ovatus (strawberry root weevil), Hylobies abietis (large brown weevil), Byctiscus betulae (Vine engraver), Anthonomus pomorum (apple blossom engraver), Anthonomus grandis (capsule beetle), Ceuthorrhynchus assimilis (cabbage weevil), Ceuthorrhynchus napi (large cabbage sprout), Sitophilus granaria (grain beetle), Anisandrus dispar (dissimilar wood bark beetle), Ips typographus (Book printer), Blastophagus piniperda (Grooved Forest Gardener); from the Order of the two-winged species (Diptera), for example Lycoria pectoralis, Mayetiola destructor (Hessian fly), Dasineura brassicae (Cabbage pod Gall mosquito), Contarinia tritici (yellow wheat gall mosquito), haplodiplosis equestris (saddle gnat), Tipula paludosa (meadow snake), Tipula oleracea (Cabbage schnapps), Dacus cucurbitae (melon fly), Dacus oleae (olive fly), Ceratitis capitata (Mediterranean fruit fly), Rhagoletis cerasi (Cherry fruit fly), Rhagoletis pomonella (apple maggot), Anastrepha ludens (Mexican fruit fly), Oscinella frit (fried fly), Phorbia coarctata (fallow fly), Phorbia antiqua (onion fly), Phorbia brassicae (small cabbage fly), Pegomya hyoscyami (beet fly), Anopheles maculipennis, Culex pipiens, Aedes aegypti (yellow fever mosquito), Aedes vexans, Tabanus bovinus (cattle brake), Tipula paludosa (meadow snake), Musca domestica (housefly), Fannia canicularis (small housefly), Muscina stabulans, Glossina morsitans (Tsetse fly), Oestrus ocis, Chrysomya macellaria, Chrysomya hominivorax, Lucilia cuprina, Lucilia sericata, hypoderma lineata;

from the order of the hymenoptera (Hymenoptera), for example Athalia rosae (beet leaf wasp), Hoplocampa minuta (plum saw wasp), Monomorium pharaonis (pharaoh ant), Solenopsis geminata (fire ant), Atta sexdens (leaf cutter ant);

from the order of the bugs (Heteroptera), for example Nezara viridula (Green rice bug), Eurygaster integriceps (Asian grain bug), Blissus leucopterus (Chinch bug), Dysdercus cingulatus (Kapok bug), Dysdercus intermedius (cotton bug), Piesma quadrata (beet bug), Lygus pratensis (common meadow bug);

from the order of the plant suckers (Homoptera) for example Perkinsiella saccharicida (sugar cane cicada), Nilaparvata lugens (brown Cicada), empoasca fabae (potato cicada), psylla mali (apple leaf suckers), Psylla piri (pear leaf suckers), Trialeurodes vaporariorum (whites  Fly), Aphis fabae (black bean louse), Aphis pomi (green apple louse), Aphis sambuci (elder aphid), Aphidula nastrutii (buckthorn aphid), Cerosipha gossypii (cucumber aphid), Sappaphis mali (rose apple), Sappaphis mala (Mealy pear aphid), Dysphis radicola (Mealy Apple plum louse), Brachycaudus cardui (large plum aphid), Brevicoryne brassicae (cabbage aphid), Phorodon humuli (hop aphid), Rhopalomyzus ascalonicus (onion), Myzodes persicae (green peach louse), Myzus cerasi (black cherry lice), Dysaulacorthum pseudosolani (Spotted Potato Louse), Acyrthosiphon onobrychis (Greens Pea Louse), Macrosiphon rosae (Greater Rose Aphid), Megoura viciae (Vetch), Schizoneura lanuginosa (pear aphid), pemphigus bursarius (lettuce root), Dreyfusia nordmannianae (fir tree louse), Dreyfusia piceae (silver fir louse), Adelges laricis (red spruce gall louse), Viteus vitifolii (phylloxera);

from the order of the termites (Isoptera), for example Reticulitermes lucifugus, Calotermes flavicollis, Leucotermes flavipes, Termes natalensis;

from the order of the straight wing aircraft (Orthoptera), for example forficula auricularia (common earwig), Acheta domestica (crickets), Gryllotalpa gryllotalpa (mole cricket), Tachycines asynamorus (greenhouse insect), Locusta migratoria (walking grasshopper), Stauronotus maroccanus (Moroccan grasshopper), Schistocerca peregrina (hiking grasshopper), Nomadacris septemfasciata (migrating grasshopper), Melanoplus spretus (rocky grasshopper), Melano plus femur-rubrum (red-legged Grasshopper), Blatta orientalis (cockroach), Blattella germanica (German cockroach), Periplaneta americana (American cockroach), Blabera gigantea (giant cockroach).

The arachnoid class includes arachnids (Acarina), for example Ixodes ricinus (woodbuck), Ornithodorus moubata, Amblyomma americanum, Dermacentor silvarum, Boophilus microplus, Tetranychus telarius, Tetranychus atlanticus, Tetranychus pacificus, Paratetranychus pilosus, Bryobia praetiosa.

The class of nemathelminths includes, for example, root gall nematodes, e.g. B. Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, Cyst-forming nematodes, e.g. B. heterodera rostochiensis, heterodera schachtii, heterodera avenae, heterodera glycines, heterodera triflolii, Stick and leaf flakes, e.g. B. Ditylenchus dipsaci, Ditylenchus destructor, Pratylenchus neglectus, Pratylenchus penetrans, Partylenchus goodeyi, Paratylenchus curvitatus and Tylenchorhynchus dubius, Tylenchorhynchus  claytoni, Rotylenchus robustus, Heliocotylenchus multicinctus, Radopholus similis, Belonolaimus longicaudatus, Longidorus elongatus, Trichodorus primitive.

The active ingredient is i. a., in the form of a formulation or the one from it prepared applications, e.g. B. in the form of directly sprayable Solutions, powders, suspensions or dispersions, emulsions, oil dispersions, Pastes, dusts, sprinkles, granules by spraying, Nebulization, dusting, scattering or pouring can be used. The application form depend entirely on the purpose; she should be in in any case the finest possible distribution of the active ingredient according to the invention guarantee.

For the production of directly sprayable solutions, emulsions, pastes or oil dispersions come mineral oil fractions from medium to high Boiling point, such as kerosene or diesel oil, as well as coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. benzene, toluene, xylene, paraffin, Tetrahydronaphthalene, alkylated naphthalenes or their derivatives, e.g. B. Methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, Cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. B. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, Water.

Aqueous application forms can be made from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water be prepared. For the production of emulsions, pastes or oil dispersions can be the substance as such or in an oil or solvent dissolved in water by means of wetting agents, adhesives, dispersants or emulsifiers be homogenized. However, network, Adhesives, dispersants or emulsifiers and possibly solvents or Oil existing concentrates are made that can be diluted with water are suitable.

Alkali, alkaline earth, ammonium salts come as surface-active substances of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, alkylarylsulfonates, Alkyl sulfates, alkyl sulfonates, alkali and alkaline earth salts dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty acid alkali and alkaline earth salts, salts of sulfated hexadecanols, Heptadecanols, octadecanols, salts of sulfated fatty alcohol glycol ether, Condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether,  ethoxylated isooctylphenol, octylphenol, nonylphenone, Alkylphenol glycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, Isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, Lauryl alcohol polyglycol ether acetal, sorbitol ester, lignin, Leaches of sulfite and methyl cellulose into consideration.

Powders, litter and dusts can be mixed or mixed Grinding the active substances with a solid carrier will.

Examples of formulations are:

I. 5 parts by weight of the compound with 95 parts by weight finely divided kaolin mixed intimately. You get one in this way Dusts containing 3% by weight of the active ingredient.

II. 30 parts by weight of the compound are made with a mixture 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil that is sprayed onto the surface of this silica gel was mixed intimately. A preparation is obtained in this way of the active ingredient with good adhesiveness.

III. 10 parts by weight of the compound are mixed solved that from 90 parts by weight of xylene, 6 parts by weight of Addition product of 8 to 10 moles of ethylene oxide with 1 mole of oleic acid N-monoethanolamide, 2 parts by weight of calcium salt Dodecylbenzenesulfonic acid and 2 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil.

IV. 20 parts by weight of the compound are mixed solved that from 60 parts by weight of cyclohexanone, 30 parts by weight Isobutanol, 5 parts by weight of the adduct of 7 moles of ethylene oxide 1 mol of isooctylphenol and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil.

V. 80 parts by weight of the connection with 3 parts by weight of Sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite Lye and 7 parts by weight of powdered silica gel mixed well and ground in a hammer mill.  

Granules, e.g. B. coating, impregnation and homogeneous granules by binding the active ingredients to solid carriers. Solid carriers are e.g. B. mineral earths, such as silica gel, silicas, Silica, silicates, talc, kaolin, attaclay, limestone, lime, chalk, Bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, Magnesium oxide, ground plastics, fertilizers such. B. ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea and vegetable Products such as flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.

The formulations generally contain between 0.1 and 95% by weight. Active ingredient, preferably between 0.5 and 90% by weight.

The active ingredient concentrations in the ready-to-use preparations can be varied in larger areas.

Generally they are between 0.0001 and 1%, preferably between 0.0001 and 0.1%.

The amount of active ingredient applied under field conditions is 0.2 to 10, preferably 0.1 to 1.0 kg / ha.

Oils of various types, herbicides, fungicides, other pesticides, bactericides, if necessary first immediately before use (tank mix). This means can to the agents according to the invention in a weight ratio of 1:10 to 10: 1 can be added.

For example, the following agents can be added:
1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 1,3-dichloropropene + 1,2-dichloropropane, 1,2-dibromoethane, 2-sec.-butylphenyl-N-methylcarbamate, o -Chlorphenyl-N-methylcarbamate, 3-isopropyl-5-methylphenyl-N-methylcarbamate, o-isopropoxyphenyl-N-methylcarbamate, 3,5-dimethyl-4-methylmercapto-phenyl-N-methylcarbamate, 4-dimethylamino-3,5 -xylyl-N-methylcarbamate, 2- (1,3-dioxolan-2-yl) -phenyl-N-methylcarbamate, 1-naphthyl-N-methylcarbamate, 2,3-dihydro-2,2-dimethyl-benzofuran-7 -yl-N-methylcarbamate, 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate, 2-dimethylamino-5,6-dimethyl-4-pyrimidinyl-dimethylcarbamate, 2-methyl-2- ( methylthio) propionaldehyde-O- (methylcarbamoyl) oxime, S-methyl-N - [(methylcarbamoyl) -oxy] -thio-acetimidate, methyl-N ′, N'-dimethyl-N- [(methylcarbamoyl) oxy] - 1-thiooxamidate, N- (2-methylchlorophenyl) -N ′, N′- dimethylformamidine,
Tetrachlorothiophene, 1- (2,6-difluorobenzoyl) -3- (4-chlorophenyl) urea, O, O-dimethyl-O- (p-nitrophenyl) phosphorothioate, O, O-diethyl-O- (p-nitrophenyl) phosphorothioate, O-ethyl-O- (p-nitrophenyl) phenyl phosphonothioate, O, O-dimethyl-O- (3-methyl-4-nitrophenyl) phosphorothioate, O, O-diethyl O- (2,4-dichlorophenyl) phosphorothioate, O-ethyl-O- (2,4-dichlorophenyl) phenylphosphonothioate, O, O-dimethyl-O- (2,4,5-trichlorophenyl) phosphorothioate, O-ethyl-O- (2,4,5-trichlorophenyl) ethyl-phosphonothioate, O, O-dimethyl-O- (4-bromo-2,5-dichlorophenyl) -phosphorothioate, O, O-dimethyl-O- (2,5-dichloro-4-iodophenyl) phosphorothioate, O, O-dimethyl-O- (3-methyl-4-methylthiophenyl) - phosphorothioate, O-ethyl-O- (3-methyl-4-methylthiophenyl) - isopropyl phosphoramidate, O, O-diethyl-O- [p-methylsulfinyl-phenyl] phosphorothioate, O-ethyl-S-phenyl-ethyl-phosphonodithioate, O, O-diethyl- [2-chloro-1- (2, 4-dichlorophenyl) vinyl] phosphate, O, O-dimethyl - [- 2-chloro-1- (2,4,5-trichlorophenyl)] - vinyl phosphate, O, O-dimethyl-S- (1 ′ -phenyl) -ethyl acetate- phosphorodithioate, bis (dimethylamino) fluorophosphine oxide, octamethyl-pyrophosphoramide, O, O, O, O-tetraethyldithio-pyrophosphate, S-chloromethyl-O, O-diethyl-phosphorodithioate, O-ethyl-S, S-dipropyl-phosphorodithioate, O, O-dimethyl-O-2,2- dichlorovinyl phosphate, O, O-dimethyl-1,2-dibromo-2,2-dichloroethyl phosphate, O, O-dimethyl-2,2,2-trichlor-1 -hydroxyethylphosphonate, O, O-dimethyl-S- [1,2-biscarbethoxy-ethyl- (1)] -phosphorodithioate, O, O-dimethyl-O- (1-methyl-2-carbmethoxy-vinyl) phosphate , O, O-Dimethyl-S- (N-methyl-carbamoyl-methyl) -phosphorodithioate, O, O-Dimethyl-S- (N-methyl-carbamoyl-methyl) -phosphorothioate, O, O-Dimethyl-S- ( N-methoxyethyl-carbamoyl-methyl) -phosphorodithioate, O, O-Dimethyl-S- (N-formyl-N-methyl-carbamoyl-methyl-phosphorodithioate, O, O-Dimethyl-O- [1-methyl-2- (methyl- carbamoyl) vinyl] phosphate, O, O-dimethyl-O - [(1-methyl-2-dimethylcarbamoyl) - vinyl] phosphate, O, O-dimethyl-O - [(1-methyl-2-chloro- 2-diethylcarbamoyl) vinyl] phosphate, O, O-diethyl-S- (ethyl-thio-methyl) -phosphorodithioate, O, O-diethy IS - [(p-chlorophenylthio) methyl] phosphorodithioate, O, O-dimethyl-S- (2-ethylthioethyl) phosphorothioate, O, O-dimethyl-S- (2-ethylthioethyl) phosphorodithioate, O, O-dimethyl-S- (2-ethylsulfinyl-ethyl) phosphorothioate, O, O-diethyl-S- (2-ethylthio-ethyl) -phosphorodithioate, O, O-diethyl-S- (2-ethylsulfinyl-ethyl) - phosphorothioate, O, O-diethyl-thiophosphoryliminophenyl-acetonitrile, O, O-diethyl-S- (2-chloro-1-phthalimidoethyl) -phosphorodithioate, O, O-diethyl-S- [6-chloro-benzoxazolone- (2) -yl (3)] - methyldithiophosphate, O, O-dimethyl-S- [2-methoxy-1,3,4-thiadiazole-5- [4H] -onyl- (4) -methyl] -phosphorodithioate, O, O -Diethyl-O- [3,5,6-trichloropyridyl- (2)] phosphorothioate, O, O-diethyl -) - O- (2-pyrazinyl) - phosphorothioate, O, O-diethyl-O [2- isopropyl-4-methyl-pyrimidinyl (6)] - phosphorothioate, O, O-diethyl-O- [2- (diethylamino) -6-methyl-4-pyrimidinyl] - thionophosphate, O, O-dimethyl-S- (4-oxo -1,2,3-benzotriazin-3- [4H] -yl-methyl) -phosphorodithioate, O, O-Dimethyl-S - [(4,6-diamino-1,3,5-triazin-2-yl) -methyl] -phosphorodithioate, O, O-diethyl- (1st -phenyl-1,2,4-triazol-3-yl) thionophosphate, O, S-dimethyl-phosphoramido-thioate, O, S-dimethyl-N-acetyl-phosphoramidothioate, alpha-hexachlorocyclohexane, 1,1- Di- (p-methoxyphenyl) - 2,2,2-trichloroethane, 6,7,8,9,10,10-hexachloro-1,5,5a, 6,9,9a- hexahydro-6,9- methano-2,4,3-benzodioxathiepin-3-oxide, pyrethrins, DL-2-allyl-3-methyl-cyclopenten- (2) -one- (1) -yl- (4) -DL-cis, trans-chrysanthate, 5-benzyl-furyl- (3) -methyl-DL-cis, trans-chrysanthemate, 3-phenoxybenzyl (±) - cis, trans-2,2-dimethyl-3- (2,2- dichlorovinyl) -cyclopropanecarboxylate, alpha-cyano-3-phenoxybenzyl (±) -cis, trans-2,2-dimethyl-3- (2,2-- dichlorovinyl-cyclopropanecarboxylate, (s) -alpha-cyano-3-phenoxybenzyl- cis (1R, 3R) - 2,2-dimethyl-3- (2,2-dibromovinyl) - cyclopropane carboxylate, 3,4,5,6-tetrahydrophthalimidoethyl-DL-cis, trans-chrysanthemate, 2-methyl-5- (2-propynyl) - 3-furylmethyl-chrysanthemate, (alpha-cyano-3-phenoxybenzyl) - alpha-isopropyl-4-chlorophenylacetate.

Application example

The compound according to the invention was compared with the structurally closest commercial product cyfen in the last example with Malathion

Contact effect on mosquito larvae (Aedes aegypti)

200 ml of tap water are mixed with the active ingredient preparation and then populated with 30-40 mosquito larvae in the 4th larval stage.

The test temperature is 20 ° C. The effect is determined after 24 hours.
Result:

Long-term effect on houseflies (Musca domestica)

Petri dishes with a diameter of 10 cm are treated on the inside with the acetone solution of the active ingredients.
After the solvent has evaporated, the dishes are filled with 20 4-day-old houseflies.
Mortality is determined after 4 hours.
Result:

Long-term effect on houseflies (Musca domestica)

Petri dishes with a diameter of 10 cm are treated on the inside with the acetone solution of the active ingredients.
After the solvent has evaporated, the dishes are filled with 20 4-day-old houseflies.
Mortality is determined after 4 hours.
Result:

Claims (6)

1. Oxime carbamate of the formula I. 2. Process for the preparation of the oxime carbamate of the formula I, characterized in that 3-chloro-2,2-dimethylpropionaldoxim (II) a) with methyl isocyanate
b) with methyl carbamic acid chloride in the presence of an acid acceptor
c) reacted with phosgene and then methylamine. 3. Pesticide containing the oxime carbamate according to Claim 1. 4. Pesticides containing a solid or liquid Carrier and the oxime carbamate of formula I. 5. Use of the oxime carbamate of the formula I for controlling pests. 6. A method for controlling pests, characterized in that an effective amount of the oxime carbamate I is applied to pests or whose habitat has an impact.