JPS5942357A - Benzamidoxime derivative and insecticide containing the same - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (X<1> is H or halogen; X<2> is halogen; Y is OH, alkoxyl, alkylaminocarboxy, alkoxycarbonylmethoxyl, etc.; Z is substituted phenyl or substituted pyridyl). EXAMPLE:N-( 4-Chlorophenylcarbamoyl )- O-( O',O'- dimethylphosphorothiono)-2,6- difluorobenzamidoxime. USE:An insecticide capable of exhibiting the activity as an active constituent in the insecticidal agent, and effective against injurious insects belonging to Plutella xylostella, carbage armyworm, housefly, common gnat, etc. PROCESS:A compound of formula II (either one of X<3> and X<4> is amino, and the other is isocyanate) is reacted with a compound of formula III to give the aimed compound of formula I . The reaction is usually carried out preferably at 0- 150 deg.C in the presence of a solvent, e.g. tetrahydrofuran (THF) or diethyl ether.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel benzamidoxime derivatives and insecticides containing them.

Specifically, the present invention relates to the general formula (1) [wherein X1 is a hydrogen atom or a halogen atom, and X! is a halogen atom, Y is a hydroxyl group, an alkoxy group, an alkylaminocarboxy group, an alkoxycarbonylmethoxy group, or a group (Y' is an oxygen atom or a sulfur atom, R1 and R3 are an alkoxy group or an alkylthio group, and n is 0 or 1
) and Z is a substituted phenyl group or a substituted pyridyl group] and insecticides containing them.

The substituted phenyl group or substituted pyridyl group represented by Z in the above general formula) means a halogen atom, trifluoromethyl group, trifluoromethoxy group, or < zl is a hydrogen atom or a halogen atom in the benzene ring or pyridine ring. a) l, Z" is a halogen atom or a trifluoromethyl group l), A is a group -CH- or a nitrogen atom) means having 1 to 4 substituents. If it has groups, they may be of the same type or of different types.

Further, the halogen atoms represented by X1, X2, Zl and Z2 include fluorine, chlorine, bromine and iodine, and the alkyl moieties of the alkoxy group, alkylaminocarboxy group and alkoxycarbonylmethoxy group represented by Y include , or the alkyl moiety of the alkoxy group and alkylthio group represented by R1 and R2 include methyl, ethyl, propyl, butyl, and the like.

The benzamide oxime derivative of the present invention is usually produced by the following method.

X8 and X4 represent an amino group and an isocyanate group, and when either one of X8 or X4 is an amino group, the other is an incyanate group. ,) This reaction is usually carried out at a temperature of 0 to 150°C in the presence of a solvent, and examples of solvents include ethers such as diethyl ether, tetrahydrofuran, and dioxane, and aromatic carbonates such as benzene, toluene, and xylene. For reactive substances such as hydrogens, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, halogenated hydrocarbons such as chloroform and chlorobenzene, and aprotic polar solvents such as dimethylbormamide and hexamethylphosphoric triamide. Inert solvents may be mentioned.

5- Next, specific synthesis examples of the compounds of the present invention will be described.

Synthesis example 1. N-(4,-chlorophenylcarbamoyl)-0-(0'.

Synthesis of 0'-dimethylphosphorothiono)-2,6-cyfluoropenzamide oxime 0-(0'0'-dimethylphosphorothiono)-2,
6-cyfluoropenzoyl isocyanate oxime 06
11 was dissolved in 80ml of dioxane, and p
-0.2 fl g of chloroaniline was gradually added, and the reaction was allowed to proceed at room temperature for 2 hours with stirring. After the reaction was completed, the product was poured into ice water and extracted with methylene chloride. The extracted layer was purified by silica gel column chromatography, and the melting point was 75.
~80°C target 0.46. fi' was obtained.

Synthesis example 2. Synthesis of N-(4,-(8-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxycarbamoylj-2,6-cyfluoropenzamide oxime 2.1 g of 6-cyfluoropenzamide oxime, 4-(8-chloro-5-trifluoromethyl-2-bididyloxy)phenylisocyanate], l,
It was dissolved in 39ml of toluene and reacted at 110°C for 8 hours with stirring. After completion of the reaction, toluene was distilled off under reduced pressure and purified by silica gel column chromatography to give a melting point of 4.0~]
11 g of the target product was obtained at -45°C.

Specific examples of the compounds of the present invention produced according to the general production method and specific synthesis examples described above will be described.

The compound of the present invention exhibits activity as an active ingredient of insecticides, especially insecticides, as shown in the test examples below. Among them, for example, Lepidoptera such as the diamondback moth, armyworm, and fall armyworm; Coleoptera such as the Colorado potato beetle and the ladybug;
It is effective against insect pests belonging to the order Diptera, such as 1'. Furthermore, some of the compounds of the present invention are effective against pests such as red-spotted spider mites, brown leafhoppers, leafhoppers, and cockroaches.

When using the compound of the present invention as an active ingredient of an insecticide, it can be formulated in various forms such as emulsions, powders, wettable powders, liquids, etc. together with pesticide adjuvants, as in the case of conventional pesticide formulations. These formulations can be used as they are, or after being diluted with a diluent to a predetermined concentration.

The pesticide adjuvants mentioned here include solid carriers such as talc, kaolin, bentonite, diatomaceous earth, white carbon, clay, and starch, and liquids such as water, xy9-lene, toluene, dimethyl sulfoxide, dimethylformamide, acetonitrile, and alcohol. Examples include diluents, emulsifiers, dispersants, and spreading agents. In addition, if necessary, it can be mixed or used in combination with other agricultural chemicals such as insecticides, acaricides, fungicides, plant growth regulators, etc. In this case, even better effects may be exhibited. For example, insecticides include organic phosphate compounds, carbamate compounds, ditheo (or thiol) carbamate compounds, organic chlorine compounds, dinitro compounds, organic sulfur or metal compounds, antibiotics,
Examples include substituted diphenyl ether compounds, urea compounds, triazine compounds, benzoyl urea compounds, and pyrethroid compounds.
-difluorobenzoyl)-N'-(p-chlorophenyl)urea, and pyrethroid compounds such as α-cyano-8-phenoxybenzyl-2-(4-chlorophenyl)isovalate.

10- The insecticide of the present invention is effective in controlling various harmful insects, especially harmful insects, and the application is generally carried out at 1 to 10° o o o p
pm, preferably at an active ingredient concentration of 20 to 2,000 ppm. Furthermore, the above-mentioned active ingredient can be mixed with feed and given to livestock to control the occurrence and growth of harmful insects, particularly harmful insects, in their excrement. In the case of aquatic harmful insects, it is possible to control them by spraying a chemical solution in the above concentration range to the place where they occur, so it is effective even if the concentration range in water is less than the above range.

Test Example 1゜Each formulation of the active ingredient compound was dispersed in water, and s
Cabbage leaf pieces were immersed in a chemical solution adjusted to a concentration of ooppm for about 10 seconds, taken out and air-dried.
A damp filter paper was placed on C1l), and the two leaf pieces were placed on top of it. Release the 2nd to B instar diamondback moth larvae there, cover the lid, and
It was left in a thermostat with lighting at 8°C. On the 8th day after the release of the insects, whether the insects were alive or dead was determined, and the mortality rate was calculated using the calculation formula of Keiki, and the results shown in Table 1 were obtained.

Table 1 Test Example 2 The procedure of Test Example 1 was repeated except that the 2- to 8-year-old diamondback moths were replaced with 2- to 8-year-old cutworms. The test was conducted in the same manner as in the case of , and the results shown in Table 2 were obtained.

Approximately 25 ml of each chemical solution of compounds 410 and 18 adjusted to a concentration of 500 ppb was placed in 4 deep-bottom petri dishes with a diameter of 9 mm.
0d, and 8th instar E. larvae were released into the container, and the container was covered with a lid and left in a lighted incubator at 28°C. After releasing insects 1
When the larvae were examined for survival on day 0, both drugs showed a 100% mortality rate.

Test Example 4 As an active ingredient compound/K 2.4.5. and 10 were used. In a cup (diameter 7 mm, height 4 mm), powdered feed (product of Oriental Yeast Co., Ltd.), bran, and chemical solutions containing each compound were added as a medium for house fly larvae in a weight ratio of l:i:8. A mixture of proportions was added, and the concentration of each compound was adjusted to sooppm. Eight-instar house fly larvae were released into the container, covered with gauze, and left there. When the number of hatchings was investigated after 10 days, 100% hatching inhibition effect was observed in all test plots.

Test Example 5 Compound M2 was adjusted to a concentration of sooppm I. Also, using the drug IB- solution, a commonly performed insecticidal test was carried out against the adult insects of the red-spotted mite, the brown-spotted planthopper, and the black-spotted leafhopper. It also showed a high insecticidal effect of 90-100%.

Formulation Example 1 (a) Compound 410 20 parts by weight (b)
N,N-dimethylformamide 70 parts by weight t
Li polyoxyethylene alkylphenyl ether 10
Parts by weight or more were uniformly mixed and dissolved to form an emulsion.

Formulation Example 2 (a) 5 parts by weight of compound rot 5 (b) 95 parts by weight or more of talc were uniformly ground and mixed to prepare a powder.

Formulation example 8 (a) Compound shop 2 50 parts by weight 14
- (b) Finely powdered silica 15 parts by weight eSaito finely powdered clay 25 parts by weight) Naphthalene sulfonic acid soda formalin condensate
2 parts by weight (e) dialkyl sulfosuccinate
8 parts by weight polyoxyethylene alkyl allyl ether sulfate
A wettable powder was prepared by uniformly crushing and mixing 5 parts by weight or more.

Patent applicant: Ishihara Sangyo Co., Ltd. 15- Continuation of page 1 0 shots clear person Toru Koyanagi 151 Ninomaru-cho, Mukojima, Fushimi-ku, Kyoto City Address 30 0 shots clear person Hiroshi Okada 424-34 Hiraicho, Kusatsu City 0 shots clear person Kiyomitsu Yoshida 424-34 Hiraicho, Kusatsu City

Claims (1)

[Claims] [In the formula, x1 is a hydrogen atom or a halogen atom; R1 and R3 are an alkoxy group or an alkylthio group, n is 0 or I), and Z is a substituted phenyl group or a substituted pyridyl group]. 2. General formula [In the formula, X1 is a hydrogen atom or a halogen atom, x8 is a halogen atom, Y is a hydroxyl group, an alkoxy group, an alkylaminocarboxylic group, an alkyl group (Y'' is an oxygen atom or a sulfur atom, and Bl and R1 is an alkoxy group or an alkylthio group, n is 0 or l, and 2 is a substituted phenyl group or a substituted pyridyl group. An insecticide characterized by