PL151684B1 - Λ Insecticide - Google Patents

Description

RZECZPOSPOLITA PATENT DESCRIPTION 151 684

POLAND

OFFICE

PATENT

RP

Additional patent to patent no - Int. Cl. ⁵ A01N 47/34

Reported: 88 02 04 (P. 270454)

Priority: 87 02 04 Japan czyteuhk

Application announced: 89 07 10 0 G 6 L M A

Patent description published: 1991 04 30

Inventors: Noriyasu Sakamoto, Tatsuya Mori, Tadashi Ohsumi, Toshihiko Yano, Izumi Fujimoto, Yoji Takada

Patent holder: Sumitomo Chemical Company, Limited,

Osaka (Japan)

Λ

Insecticide

The present invention relates to an insecticide containing benzoylurea derivatives.

Certain benzoylurea compounds with insecticidal activity are known from such publications as U.S. Patent Nos. 3,933,908,4139,636 and 4,457,943, European Patent No. 71,279A1 and Japanese Laid-Open Patent No. 106,454 / 1984, some of which include of these compounds are already commercially available.

As a result of many studies, it has surprisingly been found that the novel benzoylurea derivative of the formula I has excellent insecticidal properties, and in particular has a very strong effect on the larvae and nymphs of insect pests, and this compound can be produced at a relatively low cost. Moreover, it has been found that the compound of the formula I has an insecticidal effect that is superior to the known compounds.

The insecticide according to the invention contains the active ingredient and an inert carrier or diluent, and its feature is that it contains the active ingredient N-2,6-difluorobenzoyl N '- [2-fluoro-4- / l, 1,2-tetrafluoroethoxy [phenyl] urea of the formula I.

The compound of formula I can be prepared by reacting 2,6-difluorobenzoyl isocyanate with 2-fluoro-4 (1,2,2-tetrafluoroethoxy) aniline, or by reacting 2,6-difluorobenzamide with 2-fluoro-4- isocyanate. 1,1,2,2-tetrafluoroethoxy (phenyl). Formula 1 has a mp, mp 172-173 ° C. .

Examples of harmful insects against which the compound of formula I is particularly effective are: larvae of insects of the genus Lepidoptera, such as moth / Plutella xylostella /, rice stalk pests / Chilo suppressalis /, butterfly larvae destroying grains and owls, glitter / Plusiinae /, bielinek rzepnik / Pieris rapae crucivora /, fur moth / Tinea pellionella /, clothes moth / Tineola bisselliella / etc., larvae of harmful double-winged insects / Diptera /, such as mosquitoes / Culex spp., E.g. Culex pipiens pollena /, widliszki / Anopheles spp./, niezkwierze / Aedes spp.

151 684 dae /, mustyki etc., nymphs of harmful insects of the genus Dictyoptera such as the cockroach (Blattella germanica) and cockroaches such as Periplaneta fuliginosa, Periplaneta brunnea and the American cockroach / Periplaneta americana / etc. and the larvae of other insects belonging to the genus beetles / Coleoptera / or Hymenoptera /.

The compound of formula I is only slightly toxic to warm-blooded animals, so it can be administered orally in a mixture with food for animals, e.g. domestic animals such as cattle, pigs, horses, sheep, goats, chickens, etc. It is excreted by animals in the form of an undecomposed compound, so the larvae of insects living in the faeces of domestic animals, e.g. house fly, stable fly / Muscina stabulans /, house fly / Fannia cańicularis /, blunt / Calliphoridae /, meat flies / Saracophagidae / and Sepsidae flies can be fought against.

The insecticide according to the invention can be prepared in the form of emulsifiable concentrates, wettable powders, dusts, granules, oily spray liquids, aerosols, poisoned baits etc. For this purpose, the compound of formula I is mixed with solid, liquid or gaseous carriers, surface-active substances, other auxiliary substances, baits etc. '

The active ingredient compound of the formula I in these formulations is 0.01-95% by weight. As solid carriers, e.g. powdered or granular kaolin or attapulgite clay, bentonite, calcium sulphate, pyrophyllite, talc, diatomaceous earth, calcite, powdered maize stalks, powdered walnut shells, urea, ammonium sulphate, synthetic hydrated silicon dioxide, etc. liquid carriers are e.g. aliphatic hydrocarbons / e.g. kerosene /, aromatic hydrocarbons / e.g. benzene, toluene, xylene, methylnaphthalene /, halogenated hydrocarbons / e.g. dichloromethane, trichloroethane, carbon tetrachloride /, alcohols / e.g. methanol, ethanol, isopropanol, ethylene glycol, cellosolve /, ketones / e.g. acetone, methyl ethyl ketone, cyclohexanone, isophorone / ethers / e.g. diethyl ether, dioxane, tetrahydrofuran /, esters / e.g. ethyl acetate /, nitriles / e.g. acetonitrile, isobutyronitrile /, acid amides / e.g. dimethylformamide, dimethylacetoamide /, dimethylsulfoxide, vegetable oils / e.g. soybean oil, cottonseed oil / etc. As gaseous carriers, e.g. freon, LPG / gasol /, dimethyl ether etc. are used.

The surfactants used for emulsifying, dispersing, wetting, etc. are, for example, anionic surfactants, such as salts of alkyl sulphates, alkylarylsulphonates, dialkyl sulphosuccinates, salts of phosphoric acid esters with polyoxyethylene alkylaryl ethers, naphthalenesulphonic acid aldehyde condensation products etc., and polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc. are used as nonionic surface active substances.

As auxiliary components, binders, dispersants and the like are used, such as lignosulfonates, alginates, polyvinyl alcohol, gum arabic, molasses, casein, gelatin, carboxymethylcellulose, pine oil, agar, etc. As stabilizers, e.g., alkyl phosphates / e.g. isopropyl hydrogen phosphate PAP, TCP tricresyl phosphate, vegetable oils, epoxidized oils, the above-mentioned surface active substances, antioxidants / e.g. BHTbutylhydroxytoluene, BHA-butylhydroxyanisole /, fatty acid salts / e.g. sodium oleate, calcium stearate /, fatty acid esters / e.g. methyl oleate, methyl stearate / etc.

The formulations prepared in this way can be used as such or diluted with water, and also in mixtures with other insecticides, acaricides, nematicides, fungicides, herbicides, growth regulators, fertilizers, soil conditioners, animal feed, etc.

The compound of formula I, which is the active ingredient of the insecticide, is usually used at a dose of 0.005-5 kg / ha, the concentration of this compound in formulations in the form of emulsifiable concentrates or wettable powders etc., diluted with water, is 1-1000 ppm. . Preparations in the form of dusts, granules, oil spraying liquids, aerosols etc. are used without dilution.

The tests which compare the activity of the compound of formula I with that of the known insecticidal compounds given in Table 1 are described below.

151 684

Table 1

Symbol relationship Relationship pattern Comments AND pattern 2 Diflubenzuron, known from U.S. Patent No. 3,933,908 B pattern 3 Triflumuron, known from the patent specification United States of America No. 4 139 636 C. pattern 4 Teflubenzuron, known from the patent specification United States of America 4,457,943 D pattern 5 Compound nr 1 of European Patent Specification No. 71,279Al E. pattern 6 Compound not described in literature, melting at 158.7 ° C F. pattern 7 Compound No. 18 of the patent specification United States of America No. 4,139,636 G. formula 8 Compound No. 29 of U.S. Patent No. 4,139,636 H. pattern 9 Compound No. 1 of Japanese Laid-Open Patent No. 106454/1984 AND pattern 10 An insecticidal compound known as Methomyl

Test 1. The agent according to the invention, prepared as described in Example 1 in the form of an emulsifiable concentrate, was diluted with water so that the concentration of the active ingredient of formula I was 3.5 ppm and 100 ml of the obtained solution, diluted with water, was placed in a polyethylene cup with a capacity of 180 ml, into which 20 common mosquito larvae (Culex pipiens pallens) were introduced at the last stage of development. The larvae were reared on bait until the insects emerged, and the ratio at which the test compound inhibited exit from the larvae was determined. The test was repeated twice and the results are given in Table 2.

Table 2

Test compound The degree of inhibition of insect exit from larvae /% / Compound of formula 1 100 Control sample 10

Test 2. Emulsifiable concentrates were prepared from the compound of formula 1 and the known compounds in Table 3 as described in Example 1 and diluted with water 200,000 times to give solutions with a concentration of 0.5 ppm for each compound. 2 millimeters of each of these solutions was applied to 13 g of artificially prepared owl butterfly food (Spodeptera litura) placed in polyethylene cups with a diameter of 11 cm. Then, 10 larvae of this fourth stage butterfly were introduced into the cups, and after 6 days, the dead and alive individuals were counted to determine the mortality. The tests were carried out in duplicate and the results are given in Table 3.

151 684

Table 3

Test compound Mortality Compound of formula 1 100 AND 5 B 0 C. twenty D 5 E. 5 F. twenty G. thirty H. 10 AND 0 Control sample 5

Test 3. Emulsifiable concentrates were prepared from the compound of formula 1 and the known compounds in Table 4 as described in Example 1 and diluted with water 67,000 times to give solutions with a concentration of 1.5 ppm for each compound. 1 ml of each of these solutions was applied to 5 g of artificial food for the pest digging the pathways in the rice stalks (Chilo suppressalis). This food was contained in polyethylene cups with a diameter of 5.5 cm. Ten ten-day-old larvae of said pest were then introduced into each of these cups, and the dead and alive individuals were counted after 8 days to determine mortality. The tests were repeated twice and the results are given in Table 4.

Table 4

Test compound Mortality /% / Compound of formula 1 100 AND thirty B 5 C. 45 D 40 E. 10 F. 15 G. . 0 H. 35 AND 5 Control sample 5

The invention is illustrated by the following Examples in which the parts are parts by weight.

EXAMPLE 1 10 parts of a compound of the formula 1.14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts of dimethylformamide are thoroughly mixed to form an emulsifiable concentrate.

Example II. 20 parts of the compound of formula 1, 10 parts of O, O- (3-methyl-4-nitrophenyl) ester / phosphorothioic acid, 3 parts of calcium lignosulfonate, 2 parts of lauric sulfate and 65 parts of synthetic hydrated silicon dioxide are ground to a powder and agitates to obtain a powder for suspensions.

Example III. 1 part of the compound of formula 1, 2 parts of 1-naphthyl N-methylcarbamate, 87 parts of kaolin clay and 10 part of talcum powder are pulverized and mixed to give a dust.

Example IV. 5 parts of the compound of formula 1.1 part of the synthetic hydrated silicon dioxide, 2 parts of calcium lignosulfonate, 30 parts of bentonite and 62 parts of kaolin clay are pulverized and mixed. The resulting mixture is thoroughly kneaded with water, granulated and dried to give granules.

An insecticide containing the active substance and an inert carrier or diluent, characterized in that the active substance is N-2,6-difluorobenzoyl-N '- [2-fluoro-4 / 1,1,2,2-tetrafluoroethoxy / phenyl} urea.

151 684

Claims (1)

Patent claim FO OCF ₂ CF ₂ H / V CNHCNH II 1 \ Cl Formula 2 'y-ćnhcnh Oocf ₃ Formula 5 151 684 Formula 10 Department of Publishing of the UP RP. Circulation 100 copies Price: PLN 3,000