DK155664B - N-BENZOYL-N'-PYRIDYLOXYPHENYLURINE INGREDIENTS FOR USE IN INSECTICIDES AND INSECTICIDES CONTAINING THESE - Google Patents

Description

in

DK 155664 B

The present invention relates to novel N-benzoyl-N'-pyridyloxyphenylurea compounds for use in insecticides and insecticides containing these compounds.

Almost all conventional insecticidal compounds are neurotoxic and contact toxic to all types of insects.

Claims have been made to find selective insecticidal compounds without toxicity to useful insects. The N-benzoyl-N'-10 phenyl urea compounds known from U.S. Patent No. 3,748,356 and the N-benzoyl-N'-phenoxyphenylurea compounds (no pyridyl group) known from the specification of DK Patent Application No. 474 / 76 (corresponding to U.S. Patent No. 4,005,223) has such insecticidal properties.

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The N-benzoyl-N'-phenoxyphenylurea N-benzoyl urea compounds having insecticidal effect known from the specification for DK patent application 474/76 have the general formula: 2 ° R 3 ^ CO-NH-CO-NH ^ O - 25 r2 r4 R5 Cl where R 1 represents fluorine, chlorine, bromine or methyl, 2 R represents hydrogen, fluorine or chlorine, 3 R represents hydrogen or chlorine, R 4 represents hydrogen or chlorine or methyl, 5 R represents hydrogen or chlorine, and g R represents nitro or trifluoromethyl. .

With the present invention, new benzoyl compounds have been provided which have a remarkably more effective insecticidal effect on certain harmful insects than the above known compounds without appreciable adverse effect on useful insects and with remarkably low toxicity to animals.

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The novel compounds of the present invention are N-benzoyl-N'-pyridyloxyphenylurea compounds, which are characterized in that they have the general formula: - [- CONHCONH - (f ~ \ - o - (/ Λ_ x ^ 6

Z Y

X 4 represents X 2 represents a halogen atom or a methyl group; Xg represents a hydrogen or a halogen atom; Xg and X ^ each represent a hydrogen or a halogen atom; Xg represents a hydrogen or a halogen atom; and Xg represents a halogen atom, a nitro or a trifluoromethyl group.

Suitable compounds of formula (I) include:

Compound 20 No. 1 N- (2-chlorobenzoyl) -Ν '- [3-chloro-4- (5-bromopyridyl-2-oxy) phenyl] urea, m.p. 196-199 ° C.

2 N- (2-chlorobenzoyl) -Ν '- [3-chloro-4- (5-nitropyridyl-2-oxy) phenyl] urea, m.p. 209-212 ° C.

3 N- (2-chlorobenzoyl) -N '- [4- (3,5-di-bromopyridyl-2-oxy) phenyl] urea, m.p. 185-188 ° C.

4 N- (2-chlorobenzoyl) -N '- [3-chloro-4- (3,5-di-bromopyridyl-2-oxy) -phenyl urea, m.p. 223-224 ° C.

N- (2-chlorobenzoyl) -Ν '- [4- (3,5-dichloropyridyl-2-oxy) phenyl] urine, m.p. 216-218 ° C.

6 N- (2-chlorobenzoyl-Ν '- [3-chloro-4- (3,5-dichloropyridyl-2-oxy) -phenyl] urea, mp 225-228 ° C.

7 N- (2-chlorobenzoyl) -N '- [3,5-di chloro-4- (3,5-di chloropyridyl-2 -) oxy) phenyl] urea, m.p. 221-223 ° C.

8 N- (2-chlorobenzoyl) -N '- [4- (5-bromopyridyl-2-oxy) phenyl] urea, m.p. 179-180 ° C.

9 N- (2-chlorobenzoyl) -Ν '- [3-chloro-4- (5-chloropyridyl-2-oxy) phenyl] urea, m.p. 198-200 ° C.

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N- (2-chlorobenzoyl) -N '- [3,5-dichloro-4- (5-chloropyridyl-2-oxy) -phenyl] urea, m.p. 147-148 ° C.

11 N- (2-chlorobenzoyl) -Ν '- [4- (5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 149-151 ° C.

12 N- (2-chlorobenzoyl) -Ν '- [3-chloro-4- (5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 182-185 ° C.

13 N- (2-chlorobenzoyl) -N7- [4- (3-chloro-5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 186-187 ° C.

14 N- (2-chlorobenzoyl) -N '- [3,5-dichloro-4- (5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 206-208 ° C.

N- (2-chlorobenzoyl) -N '- [3,5-dichloro-4- (3-chloro-5-trifluoromethyl-pyridyl-2-oxy) phenyl] urea, m.p. 140-144 ° C.

N- (2-chlorobenzoyl) -Ν '- [3-chloro-4- (3-chloro-5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 224-226 ° C.

17 N- (2,6-di chlorobenzoyl) -N7 - [4- (3,5-di chloropyridyl-2-oxy) phenyl] urea, m.p. 228-230 ° C.

18 N- (2,6-dichlorobenzoyl) -N7- [3-chloro-4- (3,5-dichloropyridyl-2-oxy) phenyl] urea, m.p. 214-216 ° C.

19 N- (2,6-dichlorobenzoyl) -N7- [3,5-dichloro-4- (3,5-dichloropyridyl-2-oxy) phenyl] urea, m.p. 273-275 ° C.

N- (2,6-Difluorobenzoyl) -N '- [4- (3,5-dichloropyridyl-2-oxy) phenyl] urea, m.p. 184-185 ° C.

21 N- (2,6-Difluorobenzoyl) -N7- [3-chloro-4- (3,5-dichloropyridyl-2-oxy) phenyl] urea, m.p. 230-231 ° C.

22 N- (2,6-difluorobenzoyl) -N7- [3-chloro-4- (5-chloropyridyl-2-oxy) -phenyl] urea, m.p. 210-212 ° C.

23 N- (2,6-Difluorobenzoyl) -N7- [4- (5-trifluoromethylpyridyl-2-oxy) -phenyl] urea, m.p. 185-188 ° C.

24 N- (2,6-Difluorobenzoyl) -N7- [4- (3-chloro-5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 190-192 ° C.

N-2,6-di-fluorobenzoyl) -N7- [3-chloro-4- (5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 195-198 ° C.

26 N- (2,6-Difluorobenzoyl) -N7- [3,5-dichloro-4- (5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 209-212 ° C.

27 N-2,6-difluorobenzoyl-N7- [3,5-dichloro-4- (3-chloro-5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 203-205 ° C.

28 N- (2,6-Difluorobenzoyl) -N7- [3-chloro-4- (3-chloro-5-trifluoromethyl-pyridyl-2-oxy) phenyl] urea, m.p. 187-190 ° C.

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29 N- (2-methyl benzoyl) -Ν '- [4- (5-chloropyridyl-2-oxy) phenyl] urea substance, m.p. 198-200 ° C.

N- (2-methylbenzoyl) -N '- [4- (5-bromopyridyl-2-oxy) phenyl] urea, m.p. 188-191 ° C.

31 N- (2-methylbenzoyl) -N '- [4- (5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 140-142 ° C.

32 N- (2-methylbenzoyl) -Ν '- [3-chloro-4- (5-bromopyridyl-2-oxy) phenyl] urea, m.p. 207-209 ° C.

33 N- (2-methylbenzoyl) -N '- [3-chloro-4- (5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 188-191 ° C.

34 N- (2-methylbenzoyl) -N '- [3-chloro-4- (3,5-dichloropyridyl-2-oxy) -methyl] urea, m.p. 213-215 ° C.

N- (2-methyl benzoyl-Ν '- [3,5-dichloro-4- (3-chloro-5-trifluoromethyl-pyridyl-2-oxy) phenyl] urea, mp 214-217 ° C .

36 N- (2-methylbenzoyl) -Ν '- [3-bromo-4- (3,5-dichloropyridyl-2-oxy) -phenyl], m.p. 222-224 ° C.

37 N- (2-methyl benzoyl) -N '- [4- (3,5-dichloropyridyl-2-oxy) phenyl] urea, m.p. 216-218 ° C.

38 N- (2-methyl benzoyl) -N '- [4- (3,5-di bromopyridyl-2-oxy) phenyl] urea, m.p. 219-221 ° C.

39 N- (2-methylbenzoyl) -N '- [4- (3-chloro-5-trifluoromethyl pyridyl-2-oxy) phenyl] urea, m.p. 171-173 ° C.

N - (2-methylbenzoyl) -N '- [3,5-dichloro-4- (5-tri-fluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 219-221 ° C.

41 N- (2-methylbenzoyl) -Ν '- [3-chloro-4- (3-chloro-5-trifluoromethylpyridyl-2-oxy) phenyl] urea, m.p. 156-159 ° C.

The N-benzoyl-N'-pyridyloxyphenylurea compounds of general formula (I) can be prepared by reacting a compound of the formula: ^ X1 - CO-R3 (II) X235 λ where Xj represents a halogen atom or a methyl group; X 2 represents a hydrogen or a halogen atom and R 1 represents an amino or an isocyanate group having a compound having the formula:

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Wherein X3 and X4 are the same or different and each represents a hydrogen or a halogen atom; Xg represents a hydrogen or a halogen atom; Xg represents a halogen atom or a nitro or trifluoromethyl group and R £ represents an amino or an isocyanate group and R R is an amino group in the case that R₂ is an isocyanate group while R the case that R 1 is an amino group.

More particularly, the compounds of formula (I) can be prepared by the following processes (1) and (2).

(1) Reaction of a benzoyl isocyanate of the formula 20

f ~ \ _ v y— co-nco 25 with a pyridyloxyaniline of formula x3 x5 30 See.

4 (where Xp Xg, Xg, X4, Xg and Xg are as defined above).

(2) Reaction of a benzamide of the formula 35 ^ .χι C ° -m2 X2

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6 with a pyridyloxyphenyl isocyanate of formula X5 \ OC5-ff -O-ff-Xg X4 (where Xp X2, Xg, Xp Xg and Xg are as defined above).

The reaction is preferably carried out in the presence of a solvent. Suitable solvents include benzene, toluene, xylene and pyridine.

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The reaction temperature is usually in the range of 0-120 ° C and the reaction time is usually in the range of 0.1-24 hours. The reaction is preferably carried out at a temperature of from 50 ° C and up to reflux temperature for 1-5 hours.

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Some examples of the preparation of the compounds of the present invention will be described below.

Example 1 25

Preparation of N-(2-Chlorobenzoyl) -N- (3-chloro-4- (3,5-dichloropyril-2-oxy) phenylurea

A solution prepared by dissolving 2.9 g of 3-chloro-4- (3,5-dichloropyridyl-2-oxy) aniline in 50 ml of toluene was heated to 80 ° C. A solution prepared by dissolving 1.8 g of 2-chlorobenzoyl isocyanate in 20 ml of toluene was added dropwise to the first solution and the reaction was carried out over one hour.

After completion of the reaction, the reaction mixture was cooled and the precipitate was filtered and washed with toluene and then with petroleum ether and dried to give 3.2 g of N- (2-chlorobenzoyl) -N / - [3-chloro-4 - (3,5-Dichloropyridyl-2-oxy) phenyl] urea (mp 225-228 ° C).

Example 2

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Preparation of N-2- (6-Dichlorobenzoyl) -N / -R4- (3,5-dichloropyridyl-2-oxylohenylurea) 5

The procedure of Example 1 was repeated but with the change that 2.5 g of 4- (3,5-dichloropyridyl-2-oxy) aniline was used instead of 3-chloro-4- (3,5-dichloropyridyl). 2-oxy) aniline and 2.4 g of 2,6-dichlorobenzoyl isocyanate in place of 2-chlorobenzoyl isocyanate, and the reaction proceeded at 30 ° C for 8 hours instead of at 80 ° C for one hour to give 3, 8 g of N- (2,6-dichlorobenzoyl) -N '- [4- (3,5-dichloropyridyl-2-oxy) phenyl] urea (mp 228-230 ° C).

Example 3 15

Preparation of N- (2,6-difluorobenzoyl) -N'- [4- (3-chloro-5-trifluoro-methylloridine-2-oxyphenylurea)

The procedure of Example 1 was repeated but with the exception that 1.0 g of 4- (3-chloro-5-trifluoromethyl-pyridyl-2-oxy) aniline was used in place of 3-chloro -4- (3,5-dichloropyridyl-2-oxy) -aniline and 0.64 g of 2,6-difluorobenzoyl isocyanate in place of 2-chlorobenzoyl isocyanate, and the reaction proceeded at room temperature for 3 hours instead of 80 ° C. one hour, to give 0.5 g of N- (2.6-25 di fluoro-benzoyl) -Ν '- [4- (3-chloro-5-trifluoromethylpyridyl-2-oxy) phenyl] urea (m.p. 190-192 ° C).

Example 4 Preparation of N- (2-methylbenzoyl 1-N'-U-fS-trifluoromethyl-Dri-2-oxylphenylurea)

A solution was prepared by dissolving 0.5 g of 4- (5-trifluoromethylpyridyl-2-oxy) aniline in 20 ml of toluene. A solution prepared by dissolving 0.32 g of 2-methyl benzoyl isocyanate in 20 ml of toluene was added dropwise to the aforementioned solution and the reaction was carried out at room temperature over one hour.

Upon completion of the reaction, the reaction mixture was cooled and

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The precipitate was filtered off, washed with hexane and then recrystallized from ethanol to give 0.3 g of N- (2-methyl-benzoyl) -Ν '- [4- (5-trifluoromethylpyridyl-2-oxy) phenyl] urea (m.p. 140-142 ° C).

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Most conventional insecticides have rapid action and are neurotoxic or contact toxic. However, the compounds of the present invention have delayed effect in that the compounds affect skin ecdysis and metamorphosis of 10 particular insects that orally ingest the compound with food items or water, thereby killing the particular insects.

The compounds of the present invention have remarkable insecticidal effect on larvae of Lepidoptera, Coleoptera, Hymenoptera and Diptera, e.g. larvae of the following insects:

Plutella xvlostella (cabbage moth), Pieris rapae crucivora (common white), Mamesta brassicae (cabbage-armyworm), Plusia niarisigma (cabbage-meter! Heir), Prodenia litura ("tobacco cutworm"), Papilio xuthus 20 ("smoller citrus dog"), Seopelodes contracta ("small blackish cochlid"), Hvphantria cunea (fall snare), Lvmantria dispar ("gypsy moth"), Chilo suppressalis ("rice stalk borer") ), Heliothis zea ("seed-worm"), Heliothis virescens (tobacco budworm), Anthonomus qrandis (seed-snout beetle), Tribol ium confusum ("confus.

25 mel bi lie "), Leptinotarsa decentineata (Colorado potato beetle), Neurotoma irdescens (leaf wasps), Culex pipiens pallens (Culex mosquito), Culex pipiens molestus (mosquito).

The compounds of the present invention have no significant insecticidal effect on fully developed individuals, are inactive against natural enemies, such as predatory insects, and have low toxicity to animals.

When the compounds are used as active ingredients of insecticidal compositions, it is possible to use various auxiliary compositions, such as powder, wettable powder, emulsifiable concentrate, invert emulsion, oil solution and aerosol formulation, as is the case for compositions. agricultural use.

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The compositions may be used without or with dilution to appropriate concentrations.

Suitable adjuvants include powdered carriers such as talc, kaolin, bentonite, diatomaceous earth, silica, clay and starch; liquid diluents such as water, xylene, toluene, dimethylsulfoxide, dimethyl formamide, acetonitrile and alcohol; emulsifiers, dispersants, dispersants, etc.

The concentration of the active ingredient in the selective insecticidal composition is generally 5-80% by weight in the case of an oily concentrate, 0.5-30% by weight in the case of powder, and 5-60% by weight in the case of powder. talk about a wettable powder.

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It is also possible to combine with other agricultural ingredients, such as other insecticides, pesticides and plant growth regulators. Sometimes, synergistic effects occur.

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The selective insecticides of the present invention are effective in controlling various harmful insects and are usually used at a concentration of active ingredients of 5-10,000 ppm, preferably 20-2,000 ppm.

When the active ingredient of the present invention is used against harmful insects in water, the composition of said concentration can be used to control them, whereby the concentration of the active ingredient in the water may be lower than said concentration.

The compounds of the present invention have excellent insecticidal activity, as will be clear from the following experiments.

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Experiment 1

The active ingredients were separately dispersed in water to produce dispersions of specified concentrations.

Cabbage leaves were dipped in the dispersions for approx. 10 seconds, taken up and dried under flowing air.

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A piece of wetted filter paper was placed in each of a series of 5 petri dishes (diameter 9 cm), the dried cabbage leaves were placed on the filter paper, and larvae were placed in the second and third stages of cabbage moth fPlutella xvlostellal. whereupon the petri dishes were covered and stored at a constant temperature of 28 ° C under illumination. 8 Days after treatment with the dispersion, the number of 10 larvae was determined and mortality was calculated according to the following equation: Mortality - "" number of dead larvae χ 100 total number of larvae 15

Table 1 Mortality 1%) Mortality (%)

Compound Concentration Compound Concentration 20 No. 200 ppm 100 ppm No. 200 ppm 100 ppm 1 100 100 20 100 100 2 100 100 21 100 100 3 100 100 22 100 100 4 100 100 23 100 100 25 5 100 100 24 100 100 6 100 100 25 100 100 7 100 80 26 100 100 8 100 100 27 100 100 9 100 100 28 100 100 30 10 100 60 31 100 100 11 100 80 33 100 100 12 100 100 34 100 100 13 100 100 35 100 100 14 100 100 36 100 100 35 15 100 100 38 100 100 16 100 100 39 100 100 17 100 100 40 100 100 18 100 100 41 100 100 19 80 60

Experiment 2

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π On young radish plants grown in unglazed pots, fully developed cabbage moths (Plutella xvlostellal. 5 were retained for 24 hours for laying eggs. One day later, aqueous dispersions of the active ingredients (500 ppm) each separately, the young plants sprayed into drops of the dispersion ran off, and the leaves were dried and stored in glass greenhouses.10 Days after treatment with the dispersion, the number of dead larvae was determined, 10 and mortality was calculated according to the equation: Mortality - number of dead larvae_ x 100 total number of hatched larvae 15 The results are given in Table 2.

Table 2

Compound No. Mortality (%) 20 2 80 4 100 6 100

Experiment 3 25 o

Ca. 20 cm sprouted rice kernels were placed in cups (diameter: 9 cm; height: 3 cm) for growing. When grown to plants of 1-2 cm in height, aqueous dispersions of specified concentrations were sprayed separately at a rate of 2 cm per ml. cup.

The plants were then dried and applied to larvae (just hatched) of "rice stalk borer" (Chilo suppressalisl.) And the cups covered.

Ten days after treatment with the dispersion, the number of larvae was determined and mortality was calculated according to the equation of Experiment 1. The results are listed in Table 3.

A

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Table 3 12

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Mortality (%)

Concentration 5 Compound No. 200 pom 100 oom 1 100 100 2 100 100 4 100 100 6 100 100 10 11 100 100 12 100 100 23 100 100 24 100 100 15 Experiment 4 3 In a cup (diameter: 9 cm; height: 3 cm) got approx. 20 cm just sprouted rice kernels allowed to grow to young plants with a height of 1.5-2 3 cm. Each cup was then sprayed with 2 cm of a composition having a concentration of 400 ppm of the active ingredient, dried, and applied to third stage larvae of "child suporessalis". and the petri dish was covered. Ten days after treatment, the number of larvae was determined and mortality was calculated according to the procedure of Experiment 1. The results are listed in Table 4.

Table 4

Compound No. Mortality (%) 30 31 100 33 100 34 100 36 100 37 100 35 38 100 39 100

Experiment 5 13

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N- (2-chlorobenzoyl) -N '- [4- (3,5-dibromopyridyl-2-oxy) phenyl] urea (Compound # 3) was used to prepare the aqueous dispersions at the indicated concentrations. The effects of the dispersions on various insects were tested. The mortality 10 days after the treatments was determined according to the procedure of Experiment 1.

The results are listed in Table 5.

Table 5

Concentration Mortality 15 Insects Treatment (poml (%) Cabbage armyworm: 2nd larval stage Dipping of (Lepidoptera) cabbage leaves 50 100

Confuse flour beetle: 20 2nd larval stage Mix with (Coleoptera) wheat flour 200 100 1 sp. leaf wasp: 3rd larval stage Spraying of (Hymenoptera) cherry twigs 250 100 25

Experiment 6

Azalea leaves were dipped in aqueous solutions in each of the active ingredients (50 ppm) for 10 seconds; they were then dried in air, placed in a wide-mouthed glass bottle and applied to "gypsy moth" larvae in the second stage. The mouth of the bottle was covered with gauze and the bottle was stored in a thermostatic constant temperature bath with illumination at 28 ° C.

35 6 Days after treatment, the number of larvae was determined and mortality was calculated according to the procedure of Experiment 1.

The results are listed in Table 6.

Table 6

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Compound No. Mortality (%) 3 100 5 13 100 15 100 12 100 20 100 11 100 10 23 100 24 100 25 100 27 100 28 100 15 35 100 41 100

Experiment 7 20 Cabbage leaves were dipped in aqueous solutions of each of the active ingredients (50 ppm) for 10 seconds and then dried in air. In each petri dish (diameter: 9 cm) was placed a wet filter paper, and on each one a leaf was placed, and then second and third stage larvae of "tobacco cutworm" (Prodenia litural. Petri dish 25 was covered and was stored in a thermostatic constant temperature bath with illumination and at 28 ° C 7 Days after treatment, the number of larvae was determined and mortality was calculated according to the procedure of Experiment 1.

The results are listed in Table 7.

Table 7

Compound No. Mortality (%) 35 3 100 4 100 13 100 14 100 15 100

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15 12 100 20 100 21 100 24 100 5 25 100 26 100 33 100 35 100 39 100 10

Experiment 8 In each cup (diameter: 9 cm) was placed approx. 250 ml of an aqueous solution of the active ingredient (100 ppb). Here, 15 mosquito larvae (Culex pipiens molestus) were placed in the third stage and the cup was covered and stored in a thermostatic constant temperature bath with illumination at 28 ° C. Ten days after treatment, the number of larvae was determined and mortality was calculated according to the procedure of Experiment 1. The results are listed in Table 8.

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Compound No. Mortality (%) 3 100 8 100 11 100 25 12 100 13 100 15 100 20 100 21 100 30 23 100 24 100 25 100 27 100 28 100 35 39 100 16

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Composition 1: (a) N- (2-chlorobenzoyl) -Ν '- [3-chloro-4- (3,5-dichloropyridyl-2-oxy) phenyl] urea 20 parts by weight 5 (b) Dimethyl sulfoxide 70 parts by weight (c) Polyoxyethylene alkyl phenyl ether 10 parts by weight 10 To prepare an emulsifiable concentrate, the components were mixed to uniformity to dissolve the ingredient.

Composition 2: 15 (a) N- (2-chlorobenzoyl) -N '- [4- (3,5-dichloropyridyl-2-oxy) phenyl] urea 5 parts by weight (b) Talc 92 parts by weight 20 (c) Sodium naphthalenesulfonate formaldehyde condensate 3 parts by weight

To prepare a powder, the mixture was pulverized to uniform mixture thereof.

Composition 3: (a) N- (2,6-dichlorobenzoyl) -Ν '- [4- (3,5-dichloropyridyl-2-oxy) phenyl] urea 50 parts by weight 30 (b) Jeeklite (divided clay) 45 parts by weight (c) Sodium igninsul phonate 5 parts by weight

To prepare a wettable powder, the components were pulverized to uniform mixture thereof.

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Composition 4: (a) N- (2,6-difluorobenzoyl) -N '- [4- (3-chloro-5-tri fluoromethylpyridyl-2-oxy) phenyl] urea 20 parts by weight 5 (b) Ν, Ν -dimethylformamide 70 parts by weight (c) Polyoxyethylene alkyl phenyl ether 10 parts by weight 10 To prepare an emulsifiable concentrate, the components were mixed to uniform to dissolve the ingredient.

Composition 5: 15 (a) N- (2-chlorobenzoyl) -N '- [3,5-dichloro-4- (3-chloro-5-trifluoromethylpyridyl-2-oxy) -phenyl] urea 5 parts by weight (b) Talc 95 parts by weight 20 To prepare a powder, the mixture was pulverized to uniformity to mix it.

Composition 6: 25 (a) N- (2-methylbenzoyl) -N '- [3-chloro-4- (3-chloro-5-trifluoromethylpyridyl-2-oxy) phenyl] urea 5 parts by weight (b) Talc 95 parts by weight 30 To make a powder, the mixture was pulverized to uniformity to mix it.

Comparative Testing of Compounds of the Invention and Compounds of DK Patent Application No. 474/76 35

The compounds listed in the table below were separately dispersed in water to produce dispersions at a concentration of 1 ppm. Cabbage leaves were dipped in these dispersions for approx. 10 seconds and then taken up and dried under flowing air.

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18

A piece of moistened filter paper was placed in each of a number of petri dishes (diameter: 9 cm) and the dried cabbage leaves were placed on the filter paper and cabbage leaves (Plutella xylostella) larvae were placed in the second and third stages. whereupon the petri dishes were covered and stored at a constant temperature of 28 ° C under illumination. After 8 days from the dispersion treatment, the number of dead larvae was counted and the mortality rate was calculated by the following equation: 10 Mortality rate = Number of dead larvae χ 100

Total number of larvae

As can be seen from the results set forth in the table, the compounds of the invention exhibit a significantly greater insecticidal effect than the known compounds at the same concentration.

20 25 30 35

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Table 9 Mortality (%)

Active Ingredients (Concentration: 1 pit of C1v + - CONHCONH - ~~ \

Cl 10 (Compound No. 13 of the invention) F Cl <^^ - CONHCONH ° ~ \ ~ ^ ~ CF3 100

15 F

(Compound No. 24 of the Invention) .Cl C _ _ ~ -CONHCONH - OO “^ / CF3 100

Cl (A compound of the invention) / F / a Bvy-.

25 CQNHCQNH ° CF;} 100 F Cl (A compound of the invention) - Cl

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20.

F Cl ^^ - CONHCONH - ^^ - O -ζ> », 100

5 F

(A compound of the invention)

Cl_ ^^ - CONHCONH— ~ \ ^ y ~ CF2 100

Cl (A compound of the invention) f / -Cl Cl - 15 100 \ cr

Cl (A compound of the invention) 20 ^ \ Γ ^ ~ αοΝίκ: 0ΝΗ ~ Η \ ~~ /> ~ ° - ^ v ^ "Cf3 100 CHo (Compound No. 39 of the invention) 25 _ / F _ / C1 F. _ \ -CONHCONH — V ~ ° ~~ \ = ^ ~ CFz 100 'Cl

F

(A compound of the invention)

Cl.

- CONHCONH-O - ^ -CJ, 3 q 35 Cl (Compound according to DK Patent Application No. 474/76) 21

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_, F CL_ ^ CONHCQNH — O - \ /> - CF3 70

5 F

(Compound of DK Patent Application No. 474/76) / Cl C1v_ (^^ S-CONHCQNH

Cl (Compound of DK Patent Application No. 474/76) C1> - \ 15 ^ - ^ - CONHCONH - ^ O 55 CH1 (Compound of DK Patent Application No. 474/76) 20 25 30 35

Claims (9)

N-benzoyl-N'-pyridyloxyphenylurea for use in insecticides, characterized in that it has the general formula: _ / X 1 _ ^ 3 XfK_ i) 10 wherein Xj represents a halogen atom or a methyl group; X 2 represents a hydrogen or a halogen atom; Xg and X ^ each represent a hydrogen or a halogen atom; Xg represents a hydrogen or a halogen atom; and Xg represents a halogen atom, a nitro or a tri fluoromethyl group. 2. N-benzoyl-Ν'-pyridyloxyphenylurea according to claim 1, characterized in that it has the general formula: eye-CONHCONH -Q 25 x8 wherein 1-j and Xg each represent a hydrogen or a hal ogen atom; Xg represents a hydrogen or a halogen atom; and Xjg represents a halogen atom or a trifluoromethyl group. 30 N-benzoyl-Ν'-pyridyloxyphenylurea according to claim 2, characterized in that it has the general formula: - C ClNHCO0NH "~ \ / ° \ V" CF3 X8 wherein Xy, Xg and Xg are defined as in claim 2. DK 155664B The N-benzoyl-N'-pyridyloxyphenylurea according to claim 1, characterized in that it has the general formula: 5 X - CONHCONH - y - O X 10 where X represents a hydrogen or a halogen atom; Xg represents a hydrogen or a halogen atom; and X 2 represents a halogen atom or a trifluoromethyl group. The N-benzoyl-N'-pyridyloxyphenylurea according to claim 4, characterized in that it has the general formula: ^ CONHCONH V-O - ^ y - CFg 20 ^ x8 wherein X7, Xg and Xg are defined as in claim 4. Urea according to claim 5, characterized in that it is N- (2,6-difluorobenzoyl-N '- [3,5-dichloro-4- (3-chloro-5-tri fluoromethyl-pyridyl-2-oxy) ) phenyl] urea. Insecticide, characterized in that it contains a 30 N-benzoyl-N'-pyridyloxyphenylurea according to claim 1. Insecticide according to claim 7, characterized in that it contains 0.5-80 parts by weight of an N-benzoyl-N'-pyridyloxyphenyl urea according to claims 1 and 20-99.5 parts by weight of an excipient which can be used in agriculture. Insecticide according to claim 7, characterized in that the active ingredient is N- (2,6-difluorobenzoyl) -N '- [3,5-dichloro-4- (3-chloro-5-trifluoromethylpyridyl-2-oxy) phenyl] urea.