JPS5995294A - Urea phosphate compound, insecticide, acaricide, and nematocide containing it - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I [X<1> is H, or halogen; X<2> is halogen; Y is O, or S; R<1> and R<2> are alkoxy, or alkylthio; Z is group shown by the formula II (A is N, or =CH-; Z<1> is halogen; Z<2> is halogen, trifluoromethyl, trifluoromethoxy, 5-trifluoromethyl-2-pyridyloxy, etc.; n is 0-2)]. EXAMPLE:N-( 3-Chloro-5-trifluoromethyl-2-pyridyl )-N-( O, O-diethylphosphorothioic)-N<1>-(2,6-difluorobenzoyl)urea. USE:An insecticide, acaricide, and nematocide. PROCESS:A benzoyl isocyanate shown by the formula III is reacted with a phosphoroamide[e.g., O-ethyl-S-n-propyl-N-( 3-chloro-5-trifluoromethyl-2-pyridyl )phosphoroamidothioate, etc.] shown by the formula IV in a solvent such as toluene, etc. at 50-200 deg.C for 0.5-10hr.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel urea phosphate compounds and insecticides, acaricides, and nematicides containing them.

Specifically, the present invention is based on the general formula (1) [wherein X1 is a hydrogen atom or a halogen atom, S is a halogen atom, Y is an oxygen atom or a sulfur atom,
R and R2 are each an alkoxy group, z is a halogen atom, and 2 is a halogen 7! <child*)lifluoromethyl i,)IJ fluoromethoxy group, 5-trifluoromethyl-2-pyridyloxy group or 3-chloro-5-trifluoromethyl-2-pyridyloxy group, n is O or (an integer of 1 to 2)] and insecticides, acaricides, and nematicides containing these compounds as active ingredients.

Represented by X, X%2 and 2 in the general formula (4) -
Examples of the rogene atom include fluorine, chlorine, bromine, and iodine, and examples of the alkyl moiety of the alkoxy group and alkylthio group represented by R and R include methyl, ethyl, propyl, butyl, and the like.

The compound represented by the general formula (r) is usually a pendiyl isocyanate represented by - (wherein X and X are as defined above), and a general formula (1) (wherein Y, R%R and 2 is as described above).

The aforementioned reactions generally involve tetrahydrofuran.

Presence of solvents such as dioxannato ethers, aromatic hydrocarbons such as benzene and toluene, aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide, and halogenated hydrocarbonized ice confections such as chloroform and 1,2-dichloroethane. The reaction temperature was 50-2
00°C, reaction time is 0.5-10 hours.

In addition, the phosphoramide represented by the general formula (fit) is, for example, an amine compound NH2-Z and a +1 acid no-ride atom, and Y, Z, R' and R2 are the same as above. obtained by condensation according to the method.

Next, specific examples of synthesis of uninvented compounds will be described.

Synthesis example IN-(3-chloro-5-trifluoromethyl-
2-pyridyl)-N-(0-ethyl-3-n-propylphosphorothioic)-N'-(2,6-difluorobenzoyl)ureano synthesis 0-ethyl-8-n-propyl-N-(3 -Chloro-5
2.0 g of fluoromethyl-2-pyridyl)phosphoroamide thioney) and 1.2 g of 2,6-cyfluorobenzoyl isocyanate were dissolved in 30 m of toluene and reacted at 110°C for 5 hours with stirring. Buhi. After the reaction, toluene was distilled off under reduced pressure and purified using a silica gel column chromadog 5:1) to obtain a refractive index of /2-D1.5168.
0.6 g of the desired product was obtained.

Synthesis Example 2N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-N-(0-ethyl-8-n-propylphosphorothioic) -N"-(2, Synthesis of 6-difluorobenzoyl)urea 2.0 g of 0-ethyl-n-propyl-N-(4-(3-chloro-5-trifluoromethyl-2-p)) and 2.0 g of 6-difluorobenzoyl)urea.
0.9 g of 6-cyfluorobenzoyl isosylate and 30 ml of toluene! and reacted at 110° C. for 4 hours with stirring.

After the reaction was completed, the same purification treatment as in Synthesis Example 1 was obtained.

Specific examples of the compound represented by the general formula 0) are 1
Examples include the following:

Compound NO,IN-(3-chloro-5-trifluoromethyl-2-pyridyl)-N-(0,0-diethylphosphorothioic)-N'-(2,6-difluorobenzoyl)urea ITI, l ), 85-90°C Compound NO,2N-(3-chloro-5-trifluoromethyl-2-pyridyl) -N-(0-ethyl-8-n-propylphosphorothioic) -N'-(2 ,6-difluorobenzoyl)urea compound NO,3N-(2-chloro-4-trifluoromethylphenyl)-N-(0-ethyl-8-11-propylphosphorothioic)-N'- (z, 6 -'difluorobenzoyl)urea m, p, 165-170°C Compound NO,4N-(4-)lifluoromethoxyphenyl)-N-(Q-ethyl-8-n-propylphosphorothioic) -N'- (2,6-difluorobenzoyl)urea m, p, 84-88°C Compound NO,5N-(4-chlorophenyl)-N-(0
-ethyl-3-n-propylphosphorothioic)-N'-(2,6-difluorobenzoyl)urea Compound N0.6 solid at room temperature N-(4-(3-chloro-5-trifluoromethyl) -2-pyridyloxy)phenylin-N- (0-ethyl-8-n-propylphosphorothioic)-N'-(2,6-difluorobenzoyl)urea?LD 1.5457 Compound NO,7N-(4- Chlorophenyl)-N-(0
-Ethyl-8-n-propylphosphorothioic)-N'-(2-chlorobenzoyl)urea 9D'1.5732 The compound of the present invention has P1 insecticidal, acaricidal, and adenoidicidal properties as shown in the test examples below. It shows excellent activity as an active ingredient of a drug.

For example, plant parasitic mites such as two-spotted spider mite, false red spider mite, citrus spider mite, etc., ectoparasitic mites such as house mite, diamondback moth, armyworm, fall armyworm, Colorado potato beetle, Japanese ladybug, peach aphid, black leafhopper, red leafhopper, etc. Q-row pests such as cockroaches, houseflies, Culex mosquitoes, termites, etc., grain storage pests such as adzuki bean weevil, red-spotted beetle, etc., clothing pests such as cutworm, etc., and other livestock, etc. It is also effective against fleas and lice flies that parasitize plants, and it is also effective against harmful plant parasitic nematodes such as sweet potato nematode.

When using the compound of the present invention as an active ingredient in insecticides, acaricides, and nematocides, it can be used in combination with agricultural chemical adjuvants, such as emulsions, powders, irrigation agents, liquids, and granules, as in the case of conventional agricultural chemical formulations. They can be formulated into various forms, and 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, water, xylene, toluene, dimethyl sulfoxide, dimethyl formamide, acetonitrile,
Examples include liquid diluents such as alcohol, emulsifiers, dispersants, and spreading agents. In addition, if necessary, they can be mixed or used in combination with other agricultural chemicals such as insecticides, acaricides, fungicides, plant growth regulators, etc., and some of them may exhibit even better effects in this case.

For example, insecticides or acaricides include organic phosphate compounds, carbamate compounds, dithio (or thiol) carbamate compounds, organic chlorine compounds, dinitro compounds, organic sulfur or metal compounds, and antibiotics. , substituted diphenyl ether compounds, urea compounds, triazine compounds, benzoyl urea compounds, and pyrethroid compounds.
,6-difluorobenzoyl)-N'-(p-chlorophenyl)urea, N-(2,6-difluorobenzoyl)
-N'-[3,5-dichloro-4-(3-chloro-5-
trifluoromethyl-2-pyridyloxy)phenyl]
Examples include benzoyl urea compounds such as urea, and pyrethroid compounds such as (L-cyano-3-phenogisbenzyl-2-(4-chlorophenyl)invalerate).

The insecticide, acaricide, and nematocide of the present invention is effective for controlling various harmful insects, harmful mites, and harmful nematodes, and the application amount is generally 1 to 10,000 ppm, preferably 20 to 2,000 ppm.
Perform at 0 ppm of active ingredient.

In the case of aquatic harmful insects, it is possible to control them by spraying a chemical solution with the above concentration range to the place of occurrence, so it is effective even if the concentration range in water is below the above.Test Example 1 Preparation products of each active ingredient compound Disperse it in water and add 8%
The concentration was adjusted to 0.00 ppm. A cup (diameter 7 cm, height 4
cm), and about 30 adult two-spotted spider mites were transplanted to this.
The inoculated head is immersed in this chemical solution (2 for about 10 seconds,
After air drying, it was left in a lighted thermostat at 28°C.

On the 3rd day after the insects were released, survival and death were determined, and the mortality rate was calculated using the following calculation formula.The results are shown in Table 1. Cabbage leaves were immersed in the temperature-adjusted chemical solution for about 10 seconds, taken out, and air-dried. 9 am in diameter) Place a damp base paper on an IJ plate, and place the leaf pieces on top of it, 2 to 3 times.
The adult diamondback moth larvae were released, covered, and left in a lighted incubator at 28°C. After releasing the insects, the mortality rate was determined in the same manner as in Test Example 1 on the 5th day of the month, and the results shown in Table 2 were obtained. The test was carried out in the same manner as in Test Example 2 except that % was used, and the results shown in Table 3 were obtained.

Table 3 Test Example 4 Nos. 2, 3, 5, 6 and 7 were used as active ingredient compounds. In a cup (7 cm in diameter and 4 cm in height),
A mixture of powdered feed (product of Oriental Yeast Co., Ltd.), wheat bran, and chemical solutions of each compound in a ratio of 1:1:3 (M ratio) was added as a medium for house fly larvae, and the concentration of each compound was adjusted to 200 ppm. I made it. Third-instar house fly larvae were released into the container, covered with gauze, and dispersed. After 10 days, the number of eggs hatched was investigated.
A harmful effect of 0% on emergence l5fl was observed.

Test Example 5 Put 40g of air-dried cream into an ice cream cup, pour 10M of the chemical solution adjusted to a concentration of 400 pprn,
Mixed evenly. After 24 hours of mixing, onion fly pieces were embedded in the soil as bait, and 10 10-day-old onion fly larvae were released into the soil. After 48 hours, check whether the insects are alive or dead.
The mortality rate was determined in the same manner as in Test Example 1, and the results shown in Table 4 were obtained.

Table 4 Test Example 6 Rice seedlings were immersed in a chemical solution adjusted to a concentration of 800 ppm for 10 seconds, air-dried, the roots were wrapped with absorbent cotton, and the seedlings were placed in a test tube. In the next layer, 10 adult leafhoppers were released into this layer, and the tube opening was covered with gauze. After 3 days, the insects were examined to see if they were alive or dead, and the mortality rate was determined in the same manner as in Test Example 1, and the results shown in Table 5 were obtained.

Table 5 Test Example 7 Land contaminated with sweet potato nematode was placed in a 10,000 are pot and one tomato seedling at the 3-4 leaf stage was transplanted. Two days after the S-cut, a chemical solution of compound NO.2 adjusted to a % concentration of 400 ppm was poured into 40M/bot. At 20 days after the chemical treatment, we observed the growth status of the tomato seedlings and the degree of gall formation, and found that the results were almost the same as in the case of using soil that was not contaminated with lily bugs (no chemical treatment). Indicated.

Formulation Example 1 (a) Compound No. 6 20 parts by weight (b) N,N-dimethylformamide 70 parts by weight e→ Polyoxyethylene alkyl phenyl ether did.

Formulation Example 2 (a) Compound No. 3 5 parts by weight (b) 95 parts by weight or more of Merck were uniformly ground and mixed to form a powder.

Formulation Example 3 (a) Compound NO, 750 parts by weight (b) Fine powder silica 15 parts by weight (c) Fine powder clay 25 parts by weight) Naphthalene sulfonic acid soda formalin condensate 2
Parts by weight (4) dialkyl sulfosuccine) 3!
Amount fJ (f) Polyoxyethylene alkyl ether sulfate 5 parts by weight or more were uniformly ground and mixed to make an irrigation agent.

Patent applicant: Ishihara Sangyo Co., Ltd. 834-

Claims (1)

[Claims] 1. General formula [In the formula, XI is a hydrogen atom or a halogen atom, %X is a halogen atom, and Y is an oxygen atom or a sulfur atom]%
R1 and R2 are each alkoxy, %z1 is a halogen atom, %Z'' is a halogen atom, trifluoromethyl group, trifluoromethoxy group, 5-trifluoromethyl-
2-pyridyloxy group or 3-chloro-5-trifluoromethyl-2-pyridyloxy group, n is 0 or 1
A urea phosphate compound represented by: 2. In the general formula C, xl is a hydrogen atom or a halogen atom% X2
is a... halogen atom, Y is an oxygen atom or a sulfur atom, R and R are each an alkyl, zl is a... halogen atom, Z' is a halogen atom, a trifluoromethyl group, a trifluoromethyl group, Fluoromethoxy group% 5-trifluoromethyl-2-pyridyloxy group or 3-chloro-5-to1
1-fluoromethyl-2-pyridyloxy group, and n is an integer of 0 or 1 to 2). , nematocide.