GB1589259A - Substituted n-benzoyl n'pyridyloxy phenyl ureas and insecticidal compositions thereof - Google Patents

Substituted n-benzoyl n'pyridyloxy phenyl ureas and insecticidal compositions thereof Download PDF

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GB1589259A
GB1589259A GB1704878A GB1704878A GB1589259A GB 1589259 A GB1589259 A GB 1589259A GB 1704878 A GB1704878 A GB 1704878A GB 1704878 A GB1704878 A GB 1704878A GB 1589259 A GB1589259 A GB 1589259A
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urea
phenyl
chloro
oxy
benzoyl
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Ishihara Sangyo Kaisha Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pyridine Compounds (AREA)

Description

(54) SUBSTITUTED N-BENZOYL N PYRIDYLOXY PHENYL URREAS AND INSECTICIDAL COMPOSITIONS THEREOF (71) We, ISHIHARA SANGYO KAISHA LTD., a Japanese Company of No. 3-11, Edobori l-chome, Nishi-ku, Osaka, Japan, do hereby declare the invention, for which we pray that a patent may be granted to us and the method by which it is to be performed to be particularly described in and by the following statement:- The present invention relates to novel N-benzoyl N'-pyridyloxy phenyl ureas, to a process for producing them and to insecticidal compositions containing them.
Almost all of the conventional insecticides impart neurotoxicity and contact toxicity to all kinds of insects. There has therefore been a need for selective insecticidal compounds without toxicity to useful insects. N-benzoyl N'-phenyl ureas disclosed in USP 3,748,356 and N-benzoyl N'phenoxyphenyl ureas (no pyridyloxy group) disclosed in USP 4,005,223 have such insecticidal properties.
The N-benzoyl N'pyridyloxyphenyl ureas according to the present invention have a substantially better action than the above described known compounds against certain injurious insects without affecting useful insects and have remarkably low toxicity to animals.
The novel compounds of the present invention are N-benzoyl N'-pyridyloxy phenyl ureas having the general formula:
wherein X1 represents a fluorine or chlorine atom or a methyl group, X, represents a hydrogen or fluorine atom and Xs, X4, and X, respectively represent a hydrogen or chlorine atom, provided that when X, is chlorine X2 to X5 are not all hydrogen and when X1 and Xs are both chlorine X,, X4 and X, are not all hydrogen.
Preferred compounds in accordance with the invention and those which have the formula:
wherein X,, X4 and X are as defined above and those in which X1 and X, are both fluorine. The invention also provides herbicidal compositions comprising an N benzoyl-N'-pyridyloxy phenyl urea as defined above as an active ingredient in an agricultural adjuvant. Such compounds preferably comprise 0.5 to 80 wt. parts of the active ingredient and 20 to 99.5 wt. parts of the adjuvant.
Some preferred compounds in accordance with the invention are listed below: Compound No.
1. N - (2 - chlorobenzoyl)N' - (4 - (3 - chloro - 5 - tritluoromethylpyridyl - 2 oxy)phenyl) urea m.p. 186 to 187 C.
2. N - (2 - chlorobenzoyl)N' - (3,5 - dichloro - 4 - (5 - trifluoromethylpyridyl 2 - oxy)phenyl}urea m.p. 206 to 2080 C.
3. N - (2 - chlorobenzoyl)N' - (3,5 - dichloro - 4 - (3 - chloro - 5 - trifluoro- methylpyridyl - 2 - oxy) phenyl) urea m.p. 140 to 1440 C.
4. N - (2 - chlorobenzoyl)N' - (3 - chloro 4 - (3 - chloro 5 - trifluoromethyl pyridyl - 2 - oxy)phenyl} urea m.p. 224 to 2260 C 5. N - (2,6 - difluorobenzoyl)N' - (4 - (5 - trifluoromethylpyridyl - 2 - oy)- phenyl)urea m.p. 185 to 188 C.
6. N - (2,6 - difluorobenzoyl(N' - (4 - (3 - chloro - 5 - trifluoromethylpyridyl oxy)phenyl)urea m.p. 190 to 192 C 7. N - (2,6 - difluorobenzoyl)N' - (3 - chloro - 4 - (5 - tnfluoromethylpyridyl- 2 - oxy)phenyl)urea m.p. 195 to 1980 C.
8. N - '(2,6 - difluorobenzoyl)N' - (3,5 - dichloro - 4 - (5 - trifluoromethylpyridyl 2 - oxy)phenyl)urea m.p. 209 to 212 C.
9. N - (2,6 - difluorobenzoyl)N' - (3,5 - dichioro - 4 - (3 - chloro - 5 - difluoro- methylpyridyl - 2 - oxy)phenyl) urea m.p. 203 to 205 C.
10. N - (2,6 - difluorobenzoyl)N' - (3 - chloro - 4 - (3 - chloro - 5 - trifluoro methylpyridyl - 2 - oxy)phenyl)urea m.p. 187 to 1900 C.
11. N - (2 - methylbenzoyl)N' - (4 - (5 - trifluoromethylpyridyl - 2 - oxy-)phenyl)- urea m.p. 140 to 1420 C.
12. N - (2 - methylbenzoyl)N' - (3 - chloro - 4 - (5 - trifluoromethylpyridyl - 2 oxy)phenyl)urea m.p. 188 to 1910 C.
13. N - (2 - methylbenzoyl)N' - (3,5 - dichloro - 4 - (3 - chloro - 5 - trifluoro methylpyridyl - 2 - oxy)phenyl)urea m.p. 214 to 2170 C.
14. N -(2 - methylbenzoyl)N' - (4 - (3 - chloro - 5 - trifluoromethylpyridyl 2 - oxy)phenyl)urea m.p. 171 to 1730 C.
15. N - (2 - methylbenzoyl)N' - (3,5 - dichloro - 4 - (5 - trifluoromethylpyridyl 2 - oxy)phenyl)urea m.p. 219 to 221 C.
16. N - (2 - methylbenzoyl)N' - (3 - chloro - 4 - (3 - chloro - 5 - trifluoromethyl pyridyl - 2 - oxy)phenyl)urea m.p. 156 to 1590 C.
The N-benzoyl N'-pyridyloxy phenyl ureas having the formula (I) can be produced by reacting a compound having the formula
wherein Rl represents an amino or isocyanate group with a compound having the formula
wherein R2 is an amino group when R, is an isocyanate group and R2 is an isocyanate group when R, is an amino group and X1, X2, X,, X4 and X5 are as defined above.
More particularly, the compounds having the formula (1) can be produced by the following processes (1) and (2): (1) The reaction of a benzoyl isocyanate having the formula
with a pyridyloxy aniline having the formula
(wherein X" X2, Xs, X4 and X5 are as defined above).
(2) The reaction of a benzamide having the formula
with a pyridyloxy phenyl isocyanate having th formula
(wherein X" X,, X3, X4 and X, are as defined above).
The reaction is preferably carried out in the presence of a solvent. Suitable solvents include benzene, toluene, xylene and pyridine.
The reaction temperature is usually in a range of 0 to 1200 C and the reaction time is usually in a range of 0.1 to 24 hours. The reaction is preferably carried out at a temperature from 500 C up to the refluxing temperature for 1 to 5 hours.
An example of the preparation of a compound of the present invention will now be described.
EXAMPLE 1.
Preparation of N- (2,6-difluorobenzoyl ) N'- (4- (3-chloro-5- trifluoromethylpyridyl-2-oxy) phenyl)urea A solution prepared by dissolving 1.0 g of 3 - chloro - 4 - (3 - chloro - 5trifluoromethylpyridyl - 2 - oxy) aniline in 50 ml of toluene was heated at 800 C.
A solution prepared by dissolving 0.64 of 2,6-difluorobenzoyl isocyanate in 20 ml of toluene was added dropwise to the former solution with stirring and the reaction was carried out for 3 hours. After the reaction, the reaction mixture was cooled and the precipitate was filtered and washed with toluene and then with petroleum ether and dried to obtain 0.5 g of N - (2,6 - difluorobenzoyl)N' - (4 - (3 - chloro - 5trifluoromethylpyridyl 2 - oxy)phenyl)urea (m.p. 190 to 1920 C).
EXAMPLE 2.
Preparation of N- (2-methylbenzoyl) N'(4- ( 5-trifluoromethylpyridyl- 2-oxy) phenyl)urea 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-methylbenzoylisocyanate in 20 ml of toluene was added dropwise to the former solution under stirring it and the reaction was carried out at room temperature for 1 hour.
After the reaction, the reaction mixture was cooled and the precipitate was filtered and washed with hexane and then recrystallized from ethanol to obtain 0.3 g of N - (2 - methylbenzoyl)N' - (4 - (5 - trifluoromethylpyridyl - 2 - oxy)phenyl)urea (m.p. 140 to 1420 C).
Most of the conventional insecticides act quickly and exhibit neurotoxicity and contact toxicity. However, the compounds of the present invention have a delayed effect in that they affect the molting (ecdysis) and metamorphosis of specified insects which take the compound orally in or water so that only these specific insects are killed.
The compounds of the present invention have a remarkable insecticidal effect on the larvae of Lepidoptera, Coleoptera, Hymenoptera and Diptera, for example, larvae of the following insects: diamondback moth (Plutella xylostella), common white (Pieris rapae crucivora), cabbage armyworm (Mamestra brassicae), cabbage looper (Plusia nigrisigma), tobacco cutworm (Prodenia litura), smoller citrus dog (Papilio xuthus), small blackish cochlid (Seopelodes contacta), fall webworm (Hyphantria cunea), gypsy moth (Lymantria dispar), rice stem borer (Chilo suppressalis), bollworm (Heliothis zea), tobacco budworm (Heriothis virescens), bollweevil (Anthonomus grandis), confused flour beetle (Tribolium confusum), colorado potato beetle (Leptinotarsa decemlineata), sawfly (Neurotoma irdescens), Culex mosquito (Culex pipiens pallens), mosquito (Culex pipiens molestus).
The compounds of the present invention have substantially no insecticidal effect on adult insects and are ineffective against natural enemies of pests such as predatory insects and have low toxicity to animals.
When the compounds of the invention are used as active ingredients of insecticidal compositions, it is possible to prepare various forms of composition such as dust, wettable powder, emulsifiable concentrate, invert emulsion, oil solution and aerosol preparations, with adjuvants in the case of agricultural compositions. The compositions can be applied with or without diluting to suitable concentrations.
Suitable adjuvants include powdery carriers such as talc, kaolin, bentonite, diatomaceous earth, silicon dioxide, clay and starch; liquid diluents such as water, xylene, toluene, dimethylsulfoxide, dimethyl formamide, acetonitrile, and alcohol; emulsifiers; dispersing agents spreaders.
The concentration of the active ingredient in the selective insecicidal composition is usually 5 to 80 wt. % in the case of the oily concentrate; and 0.5 to 30 wt. % in the case of dust and 5 to 60 wt. % in the case of wettable powder.
It is also possible to combine with other agricultural ingredients such as other insecticides, miticides, plant growth regulators. Sometimes synergistic effects are found.
The selective insecticides of the present invention are effective for inhibiting various injurious insects and they are usually applied at a concentration of the active ingredients of 5 to 10,000 ppm preferably 20 to 2,000 ppm.
When the active ingredient of the present invention is applied to noxious insects in water the composition having said concentration can be applied to inhibit them, whereby the concentration of the active ingredient in water can be lower than said concentration.
Experiment 1: The active ingredients were respectively dispersed in water to prepare dispersions having specified concentrations. Cabbage leaves were dipped into the dispersions for about 10 seconds and taken out and dried under air.
A piece of moistened filter paper was put on each of several Petri dishes (diameter 9 cm), the dried cabbage leaves were put on the filter paper and diamondback moth larvae in 2nd or 3rd instar were fed on them and the Petri dishes were covered and kept at constant temperature at 280 C with light After 8 days from the treatment with the dispersion, the living and dead larvae were counted and the mortality rates were calculated by the following equation: dead larvae Mortality rate = - X X 100 total larvae TABLE 1
Mortality rate (inc) (concentration) Compound No. 200 ppm 100 ppm 1 100 100 2 100 100 3 100 100 4 100 100 5 100 100 6 100 100 7 100 100 8 100 100 9 100 100 10 100 100 11 100 100 12 100 100 13 100 100 14 100 100 15 100 100 16 100 1 100 Experiment 2: About 20 cc of germinated rice seeds were put into cups (diameter: 9 cm, height: 3 cm)- to grow. When they grew to seedlings having a height of 1 to 2 cm, aqueous dispersions at specified concentrations were respectively sprayed at a ratio of 2 cc per cup and dried, larvae of rice stem borer (just hatched) were fed and the cups were covered. After 10 days from the treatment with the dispersion, the dead larvae were counted and the mortality rates were calculated by the equation of Experiment 1. The results are shown in Table 2.
TABLE 2
Mortality rate (NO) (concentration) Compound No. 200 ppm 100 ppm 5 100 100 6 100 100 Experiment 3: In a cup (diameter of 9 cm; height of 3 cm), about 20 cc of emerged rice seeds were planted to grow to young seedlings having a height of 1.5 to 2 cm and then 2 cc of a composition having a 400 ppm concentration of one of the active ingredients in Table 3 below was sprayed per 1 cup, and dried and larvae of rice stem borer in 3rd instar were fed on them and each Petri dish was covered. After 10 days from the treatment, the dead larvae were counted and the mortality rates were calculated in accordance with the method of Experiment 1. The results are shown in Table 3.
TABLE 3
Compound Mortality rate Compound Mortality rate No. (io) 11 100- 12 100 14 100 Experiment 4: A cabbage leaf was dipped in an aqueous solution of compound No. 1 (50 ppm) for 10 seconds, and dried in air. A wet filter paper was disposed in a Petri dish (diameter of 9 cm), the leaf was put on the filter paper and larvae of tobacco cutworm in 2nd or 3rd instar were fed thereon. The Petri dish was covered and kept in a thermostat-controlled constant temperature bath with light at 280 C. After 7 days the dead larvae were counted and the mortality rate was 100% calculated in accordance with the method of Experiment 1.
Experiment 5: In a series of cups (diameter of 9 cm), about 250 ml of aqueous solutions each of compounds 1, 3, 5, 6, 7, 8, 9, 10 and 14 (100 ppb) was charged, together with mosquito larvae (Culex pipiens molestus) in 3rd instar. The cups were covered and kept in a thermostat-controlled constant temperature bath with light at 280 C.
After 10 days from the treatment, the dead larvae were counted and the mortality rates were calculated in accordance with the method of Experiment 1. A mortality rate of 100% was found in each case.
Typical insecticidal composition in accordance with the invention were prepared as follows: Composition 1: (a) N - (2,6 - difluorobenzoyl)N' - [4 - (3 chloro - 5 - trifluoromethylpyridyl 2 - oxy)phenvl]urea 20 wt. parts (b) N,N-dimethylformamide 70 wt. parts (c) Polyoxyethylenealkylphenyl ether 10 wt. parts The components were uniformly blended to dissolve the active ingredient and prepare an emulsifiable concentrate.
Composition 2: (a) N - (2 - chlorobenzoyl)N' - [3,5 - dichloro -4 - (3 - chioro - S - tri- fluoromethylpyridyl - 2 - oxy)phenyl] urea S wt. parts (b) Talc 95 wt. parts The mixture was pulverized and uniformly mixed to prepare a dust.
Composition 3.
(a) N - (2 - methylbenzoyl)N' - [3 - chloro - 4 - (3 - chloro - 5- trifluoro methylpyridyl - 2 - oxy)phenyl] urea 5 wt. parts (b) Talc 95 wt. parts The mixture was pulverized and uniformly mixed to prepare a dust.
WHAT WE CLAIM IS: 1. An N-benzoyl N'-pyridyloxy phenyl urea having the formula
wherein X1 represents a fluorine or chlorine atom or a methyl group; X2 represents a hydrogen or fluorine atom and X3, X4 and Xs respectively represent a hydrogen or chlorine atom; provided that when X1 is chlorine X2 to X5 are not all hydrogen and when X1 and Xs are both chlorine, X2, X4 and Xs are not all hydrogen.
2. An N-benzoyl N'-pyridyloxy phenyl urea according to claim 1 wherein X1 is chlorine and X2 is hydrogen.
3. N - (2 - chlorobenzoyl)N' - {4 - (3 - chloro - 5 trifluoromethylpyridyl2-oxy)phenyl)urea.
4. N - (2 - chlorobenzoyl)N' - (3,5 - dichloro - 4 - (5 - trifluoromethylpyridyl 2 - oxy)phenyl)urea.
5. N - (2 - chlorobenzoyl)N' - (3,5 - dichloro - 4 - (3 - chloro - 5 - trifluoro methylpyridyl - 2 - oxy)phenyl)urea.
6. N - ( 2 - chlorobenzoyl)N' - {3 - chloro - 4 - (3 - chloro - 5 - trifluoro methylpyridyl - 2 - oxy)phenyl)urea.
7. An N-benzoyl N'-pyridyloxy phenyl urea according to claim 1 wherein Xl and X2 are both fluorine.
7. N - (2,6 - difluorobenzoyl)N' - (4 - (3 - chloro - 5 - trifluoromethylpyridyl - 2 - oxy)phenyl)urea.
8. N - (2,6 - difluorobenzoyl)N' - (3,5 - dichloro - 4 - (5 - trifluoromethylpyridyl - 2 - oxy)phenyl)urea.
9. N - (2,6 - difluorobenzoyl(N' - (3,5 - dichloro - 4 - (3 - chloro - 5 - trifluoromethylpyridyl - 2 - oxy)phenyl)urea.
10. N- (2,6 - difluorobenzoyl)N' - (3 - chloro 4 (3 - chloro - 5 - trifluoro- methylpyridyl - 2 - oxy)phenyl)urea.
11. An N-benzoyl N'-pyridyl phenyl urea according to claim 1 wherein Xi is a methyl group and X2 is hydrogen.
12. N - (2 - methylbenzoyl)N' - (3 - chloro - 4 - (5 - trifluoromethyl - pyridyl 2 - oxyphenyl))urea.
13. N - (2 - methylbenzoyl)N' - (3,5 - dichloro - 4 - (3 - chloro - 5 - tri- fluoromethylpyridyl 2 - oxy) phenyl)urea.
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (26)

  1. **WARNING** start of CLMS field may overlap end of DESC **.
    Typical insecticidal composition in accordance with the invention were prepared as follows: Composition 1: (a) N - (2,6 - difluorobenzoyl)N' - [4 - (3 chloro - 5 - trifluoromethylpyridyl
    2 - oxy)phenvl]urea 20 wt. parts (b) N,N-dimethylformamide 70 wt. parts (c) Polyoxyethylenealkylphenyl ether 10 wt. parts The components were uniformly blended to dissolve the active ingredient and prepare an emulsifiable concentrate.
    Composition 2: (a) N - (2 - chlorobenzoyl)N' - [3,5 - dichloro -4 - (3 - chioro - S - tri- fluoromethylpyridyl - 2 - oxy)phenyl] urea S wt. parts (b) Talc 95 wt. parts The mixture was pulverized and uniformly mixed to prepare a dust.
    Composition 3.
    (a) N - (2 - methylbenzoyl)N' - [3 - chloro - 4 - (3 - chloro - 5- trifluoro methylpyridyl - 2 - oxy)phenyl] urea 5 wt. parts (b) Talc 95 wt. parts The mixture was pulverized and uniformly mixed to prepare a dust.
    WHAT WE CLAIM IS: 1. An N-benzoyl N'-pyridyloxy phenyl urea having the formula
    wherein X1 represents a fluorine or chlorine atom or a methyl group; X2 represents a hydrogen or fluorine atom and X3, X4 and Xs respectively represent a hydrogen or chlorine atom; provided that when X1 is chlorine X2 to X5 are not all hydrogen and when X1 and Xs are both chlorine, X2, X4 and Xs are not all hydrogen.
  2. 2. An N-benzoyl N'-pyridyloxy phenyl urea according to claim 1 wherein X1 is chlorine and X2 is hydrogen.
  3. 3. N - (2 - chlorobenzoyl)N' - {4 - (3 - chloro - 5 trifluoromethylpyridyl2-oxy)phenyl)urea.
  4. 4. N - (2 - chlorobenzoyl)N' - (3,5 - dichloro - 4 - (5 - trifluoromethylpyridyl 2 - oxy)phenyl)urea.
  5. 5. N - (2 - chlorobenzoyl)N' - (3,5 - dichloro - 4 - (3 - chloro - 5 - trifluoro methylpyridyl - 2 - oxy)phenyl)urea.
  6. 6. N - ( 2 - chlorobenzoyl)N' - {3 - chloro - 4 - (3 - chloro - 5 - trifluoro methylpyridyl - 2 - oxy)phenyl)urea.
    7. An N-benzoyl N'-pyridyloxy phenyl urea according to claim 1 wherein Xl and X2 are both fluorine.
  7. 7. N - (2,6 - difluorobenzoyl)N' - (4 - (3 - chloro - 5 - trifluoromethylpyridyl - 2 - oxy)phenyl)urea.
  8. 8. N - (2,6 - difluorobenzoyl)N' - (3,5 - dichloro - 4 - (5 - trifluoromethylpyridyl - 2 - oxy)phenyl)urea.
  9. 9. N - (2,6 - difluorobenzoyl(N' - (3,5 - dichloro - 4 - (3 - chloro - 5 - trifluoromethylpyridyl - 2 - oxy)phenyl)urea.
  10. 10. N- (2,6 - difluorobenzoyl)N' - (3 - chloro 4 (3 - chloro - 5 - trifluoro- methylpyridyl - 2 - oxy)phenyl)urea.
  11. 11. An N-benzoyl N'-pyridyl phenyl urea according to claim 1 wherein Xi is a methyl group and X2 is hydrogen.
  12. 12. N - (2 - methylbenzoyl)N' - (3 - chloro - 4 - (5 - trifluoromethyl - pyridyl 2 - oxyphenyl))urea.
  13. 13. N - (2 - methylbenzoyl)N' - (3,5 - dichloro - 4 - (3 - chloro - 5 - tri- fluoromethylpyridyl 2 - oxy) phenyl)urea.
  14. 14. N - (2 - methylbenzoyl)N' - (4 - (3 - chloro - 5 - trifluoromethylpyridyl
    2 - oxy)phenyl)urea.
  15. 15. N - (2 - methylbenzoyl)N' - (3 - chloro - 4 - (3 - chloro - 5 - trifluoromethylpyridyl - 2 - oxy)phenyl)urea.
  16. 16. Any one of the compounds numbered 1 to 16 herein.
  17. 17. An insecticidal composition which comprises as an active ingredient an N-benzoyl N'-pyridyloxy phenyl urea having the formula (I) according to any preceding claim in an agricultural adjuvant.
  18. 18. An insecticidal composition according to claim 17 which comprises 0.5 to 80 wt. parts of N-benzoyl N'-pyridyloxy phenyl urea having the formula (I) and 20 to 99.5 wt. parts of the agricultural adjuvant.
  19. 19. An insecticidal composition according to claim 17 substantially as herein described with reference to any one of composition Nos. 1 to 3.
  20. 20. A process for producing an N-benzoyl N'-pyridyloxy phenyl urea according to claim 1 which comprises reacting a compound having the formula
    wherein X1 and X2 are as defined in claim 1 and R1 represents an amino or isocyanate group; with a compound having the formula
    wherein R2 represents an amino group when Ri is an isocyanate group, and an iso cyanate group when R1 is an amino group and Xi, X > , X4 and Xs are as defined in claim 1.
  21. 21. A process according to claim 20 wherein the reaction is carried out in a solvent at a temperature from room temperature up to the refluxing temperature.
  22. 22. A process according to claim 20 or claim 21 which comprises reacting a benzoyl isocyanate having the formula
    with a pyridyloxy aniline having the formula
    wherein X, Xi, X3, X4 and Xs are as defined in claim 1.
  23. 23. A process according to claim 20 or claim 21 which comprises reacting benzamide having the formula
    with pyridyloxy phenyl isocyanate having the formula
    wherein Xte X9, X, X4 and X, are as defined in claim 1.
  24. 24. A process according to claim 22 substantially as herein described and exemplified.
  25. 25. A process according to claim 23 substantially as herein described.
  26. 26. A substituted N-benzoyl N'-pyridyloxy phenyl urea made by a process according to any one of claims 20 to 25.
GB1704878A 1978-04-28 1978-04-28 Substituted n-benzoyl n'pyridyloxy phenyl ureas and insecticidal compositions thereof Expired GB1589259A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2141628A (en) * 1983-05-30 1985-01-03 Ciba Geigy Ag Synergistic pesticidal compositions
US4677127A (en) * 1981-11-10 1987-06-30 Ciba-Geigy Corporation Certain N-3-(3-chloro-5-trifluoromethyl-pyridyl-2-oxy)-4-phenyl-N'-2,6-difluorobenzoyl ureas, pesticidal compositions and methods of use
US6576661B1 (en) 1999-11-09 2003-06-10 Bayer Aktiengesellschaft Active ingredient combination having insecticidal and acaricidal characteristics

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4677127A (en) * 1981-11-10 1987-06-30 Ciba-Geigy Corporation Certain N-3-(3-chloro-5-trifluoromethyl-pyridyl-2-oxy)-4-phenyl-N'-2,6-difluorobenzoyl ureas, pesticidal compositions and methods of use
US4687855A (en) * 1981-11-10 1987-08-18 Ciba-Geigy Corporation Certain 3-trifluoromethyl-5-chloro-2-pyridyloxy-aniline intermediates
US4897486A (en) * 1981-11-10 1990-01-30 Ciba-Geigy Corporation 5-trifluoromethylpyridyl-2-oxy-4-fluoroanilines as intermediates
GB2141628A (en) * 1983-05-30 1985-01-03 Ciba Geigy Ag Synergistic pesticidal compositions
US6576661B1 (en) 1999-11-09 2003-06-10 Bayer Aktiengesellschaft Active ingredient combination having insecticidal and acaricidal characteristics
US6818670B2 (en) 1999-11-09 2004-11-16 Bayer Aktiengesellschaft Active ingredient combination having insecticidal and acaricidal characteristics

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