Benzoazine ether or thioether linkage containing urea compounds, process for producing same and insecticides containing said compounds

Abstract

This invention relates to a heterocyclic ether or thioether linkage containing urea compounds of the following formula I: ##STR1## wherein B denotes an oxygen atom or a sulfur atom, A denotes CH or a nitrogen atom, X.sup.1 and X.sup.2 denote independently of each other hydrogen atom, halogen atom, trifluoromethyl group or nitro group, Y and Z denote independently of each other hydrogen atom or halogen atom, and P and Q denote independently of each other hydrogen atom, halogen atom, alkoxyl group or alkyl group, a process for producing the same and an insecticide containing the same.

Description

BACKGROUND OF THE INVENTION

This invention relates to a novel heterocyclic ether or thioether linkage containing urea compounds, a process for producing the same and an insecticides containing the same.

A variety of insecticides have been put to practical use by years of research and development of insecticides, and these insecticides have contributed to improvement of the productivity of agricultural and horticultural product.

However, there is still a need to develop novel insecticides having more excellent insecticidal properties.

Concerning heterocyclic ether or thioether linkage containing urea compounds, Japanese Patent Application Laid-Open No. 106475/1979 describes that substituted ether linkage containing urea compounds can be used as insecticides. Also, Japanese Patent Application Laid-Open No. 98153/1980 describes naphthyl ether linkage containing urea compounds and insecticidal action thereof.

The heterocyclic ether or thioether linkage containing urea compounds having a quinoline or quinoxaline skeleton, however, are novel compounds which have not been described in literature. After strenuous effort in developing novel and useful insecticides, the present inventors have newly found such compounds.

SUMMARY OF THE INVENTION

An object of this invention is to provide novel heterocyclic ether or thioether linkage containing urea compounds having an excellent insecticidal activity.

Another object of this invention is to provide insecticides containing a novel heterocyclic ether or thioether linkage containing urea compound as an active ingredient.

Still another object of this invention is to provide a process for producing novel heterocyclic ether or thioether linkage containing urea compounds.

These and other objects of this invention will be more apparent from the following detailed description and examples.

DETAILED DESCRIPTION

The novel compound of this invention is represented by the following formula I: ##STR2## wherein B denotes an oxygen atom or a sulfur atom, A denotes CH or a nitrogen atom, X.sup.1 and X.sup.2 denote independently of each other hydrogen atom, halogen atom, trifluoromethyl group or nitro group, Y and Z denote independently of each other, hydrogen atom or halogen atom, and P and Q denote independently of each other hydrogen atom, halogen atoms, alkoxyl groups or alkyl groups.

In general, the compounds of this invention can be prepared according to a method represented by the following reaction formula: ##STR3## wherein B, A, X.sup.1, X.sup.2, Y, Z, P and Q have the same meanings as above.

Namely, the compounds of this invention can be prepared by condensing a benzoyl isocyanate represented by the general formula II with an aniline derivative represented by the general formula III, preferably in the presence of an inert solvent to the reactants.

As the reaction solvent, there is used a solvent such as benzene, toluene, acetonitrile or pyridine.

The reaction temperature and time may vary according to starting materials, and usually, a reaction temperature ranging from -20.degree. C. to 100.degree. C. and a reaction time ranging from 0.5 hour to 24 hours are preferred.

The compound of the formula III can be prepared as follows: ##STR4## wherein B, A, X.sup.1, X.sup.2, Y, Z denote the same meanings given in the formula I.

The thus-prepared compounds of this invention are compounds which are extremely useful as agents for controlling and combating sanitary insect pests as well as insect pests of forest, insect pests in stored corps and agricultural and horticultural insect pests which damage paddy-rice plants, vegetables, fruit trees, cotton plants and other crops and flowering plants.

According to this invention, there are provided insecticides which are used to sprinkle an effective amount of the compound of this invention together with a suitable carrier over habitats of insect pests.

Habitats of insect pests mean any areas where insects live, including soil, air, water, foods, plants, fertilizers, inert substances and stored products such as crops.

The following are examples of insect pests to which the compounds of this invention are applicable. Of course, these examples are non-limitative.

Sanitary insect pests:

housefly (Musca domestica), mosquito (Culex spp., Aedes spp., Anopheles spp.) cockroach (Periplaneta spp., Blatella spp.)

Agricultural and horticultural insect pests:

(Insect pests of rice)

rice stem borer (Chilo suppressalis), rice leaf beetle (Oulema oryzae), ricewater weevil (Lissothoptrus oryzophilus), rice leaf miner (Agromyza oryzae), smaller rice liaf miner (Hydrellia griseola), small brown planthopper (Laodelphax striatella), white-backed planthopper (Sogatella furcifera), brown planthopper (Nilaparvata lugens), green rice leafhopper (Nephotettix cincticeps)

(Vegetable insect pests)

cabbage armyworm (Mamestra brassicae), tobacco cutworm (Spodoptera litura), common white (Pieris rapae crucivora), diamondback moth (Plutella xylostella), 28-spotted lady bettle (Epilachna vigintioctopunctata), Green peach aphid (Myzus persicae)

(Insect pest of tree fruit)

tortrix, Leafrolles (Adoxophyes spp., Archeps spp., Archi ppus spp.), apple leafminer (Phyllonorycter ringoneella), oriental fruit moth (Grapholita molesta), peach fruit moth (Carposina niponensis), smaller tea tortrix (Adoxophyes orana), comstock mealybug (Pseudococcus comstocki)

The insecticidal action of the compounds of this invention is considered to consist in the disturbance of metamorphic mechanisms of insect pests, with consequent kills of them. For producing this action, it is considered necessary that insect pests take in the compound. Although, in certain insect pests, their deaths postpone until they enter the metamorphosis stages, the actual effects of this activity result in the control and combat of them. Insecticides comprising the compounds of this invention have effectiveness also against early instar larvae and late instar larvae, and their effectiveness appears directly or systemically.

In applying the insecticides of this invention, it is preferable to use the agent usually in an active ingredient concentration of 0.1-10,000 ppm, and preferably 0.5-2,000 ppm. In case of insect pests living in water, applying of the agent in the above concentration range over breeding areas can control the insects, and therefore, concentrations in the water outside the above range are also effective.

When the compounds of this invention are used as an insecticides, the compounds are applied in admixture with a suitable carrier, e.g., a solid carrier such as clay, talc or bentonite, or a liquid carrier such as water, alcohol (methanol or ethanol), a ketone, an ether, aliphatic hydrocarbons, aromatic hydrocarbons (benzene, toluene or xylene) an organic base, acid amide (dimethylformamide), esters or nitriles in the dissolved, dispersed, suspended, blended, immersed, adsorbed or adhered state. If necessary, the insecticides of this invention can contain an emulsifier, a dispersant, a suspending agent, a spreader, a penetrant or a stabilizer, and can be used in any form of emulsions, oils, wettable powders, dusts, granules, tablets, pastes, flowables, aerosols, fumigant, mosquito, incense stick or electric mosquito mat.

Also, if desired, at the time of formulation or application, the insecticides of this invention can be mixed or simultaneously applied with different insecticides, various germicides, herbicides, plant-controlling agent and fertilizers.

Still higher insecticidal action can be obtained by adding to the compounds of this invention, a synergist such as piperonyl butoxide, octachlorodipropyl ether or N-octylbicycloheptane dicarboximide.

Also, the stability of the compounds of this invention can be increased by adding thereto as an antioxidant, a phenolic compound such as 2,6-di-tert-butyl-4-methylphenol or 2,6-di-tert-butylphenol or other amines.

This invention is illustrated in further detail below with reference to examples, formulations and tests, but not limited thereto.

EXAMPLE 1

Preparation of N-(2,6-dichlorobenzoyl)-N'-4-(2-quinolyloxy)phenyl urea (compound No. 30) represented by the following formula: ##STR5##

To a solution of 1.2 g (5.0.times.10.sup.-3 mol) of 4-(2-quinolyloxy)aniline in 40 ml of acetonitrile was added dropwise with stirring at 0.degree. C., 1.0 g (4.6.times.10.sup.-3 mol) of 2,6-dichlorobenzoyl isocyanate. The reaction mixture was allowed to react overnight at room temperature, and the crystal formed was filtered off, washed with acetonitrile and dried to yield 1.5 g of the desired compound (compound No. 30) as a white crystal, m.p. 234.degree.-235.5.degree. C.

EXAMPLE 2

Preparation of N-(2,6-dimethoxybenzoyl)-N'[-3-chloro-4-(6-fluoro-2-quinoxalyloxy)phenyl]urea (compound No. 38) represented by the following formula: ##STR6##

To a solution of 0.87 g (3.0.times.10.sup.-3 mol) of 3-chloro-4-(6-fluoro-2-quinoxalyloxy)aniline in 30 ml of acetonitrile was added dropwise with stirring at 0.degree. C., 0.6 g (2.9.times.10.sup.-3 mol) of 2,6-dimethoxybenzoyl isocyanate. The reaction mixture was allowed to react overnight at room temperature, and the crystal formed was filtered off, washed with acetonitrile and dried to yield 1.0 g of the desired compound (compound No. 38) as a white crystal, m.p. 227.degree.-229.degree. C.

EXAMPLE 3

Preparation of N-(2-chlorobenzoyl)-N'[-4-(6-chloro-2-quinoxalyloxy)phenyl]urea (compound No. 10) represented by the following formula: ##STR7##

To a solution of 1.1 g (4.0.times.10.sup.-3 mol) of 4-(6-chloro-2-quinoxalyloxy)aniline in 40 ml of acetonitrile was added dropwise with stirring at 0.degree. C., 0.7 g (3.9.times.10.sup.-3 mol) of 2-chlorobenzoyl isocyanate. The reaction mixture was allowed to react overnight at room temperature, and the crystal formed was filtered off, washed with acetonitrile and dried to yield 1.1 g of the desired compound (compound No. 10) as a white crystal, m.p. 238.degree.-240.degree. C.

In the same manner as in the above examples, compounds listed in the following tables 1 and 2 were prepared. Preparation of compounds represented by the following formula Ia: ##STR8##

TABLE 1__________________________________________________________________________CompoundNo. A B X.sup.1 X.sup.2 R.sup.1 R.sup.2 R.sup.3 R.sup.4 Properties m.p. (.degree.C.)__________________________________________________________________________1 N O H H H H F F white crystal 218-2192 N O H H H H Cl H white crystal 241-2423 N O H H H H Cl Cl white crystal 228-2304 N O H H Cl Cl F F white crystal 215-2175 N O H H Cl Cl Cl H white crystal 205-2076 N O H H Cl Cl Cl Cl white crystal 251-2537 N S H H H H Cl Cl white crystal 222-2248 N S H H H H F F white crystal 224-2269 N O 6-Cl H H H F F white crystal 227-22811 N O 6-Cl H H H Cl Cl white crystal 225-22612 N O 6-Cl H Cl H F F white crystal 236-23813 N O 6-Cl H Cl H Cl H white crystal 227-22814 N O 6-Cl H Cl H Cl Cl white crystal 239-24015 N O 6-Cl H Cl Cl F F white crystal 229-23016 N O 6-Cl H Cl Cl Cl H white crystal 244-24617 N O 6-Cl H Cl Cl Cl Cl white crystal 255-25618 N S 6-Cl H H H F F white crystal 236-23919 N O 6-F H H H Cl H white crystal 238-23920 N O 6-F H Cl H F F white crystal 227-23021 N O 6-F H Cl H Cl H white crystal 227-23122 N O 6-F H Cl H Cl Cl white crystal 245-24623 N O 6-F H Cl Cl F F white crystal 222-22524 N O 6-F H Cl Cl Cl H white crystal 224-22525 N O 6-F H Cl Cl Cl Cl white crystal 241-24426 N O 6-NO.sub.2 H Cl Cl F F white crystal 275.degree. C. - decomp.27 N O 6-NO.sub.2 H Cl Cl Cl H white crystal 257-26028 N O 6-NO.sub.2 H Cl Cl Cl Cl white crystal 285.degree. C. - decomp.29 N O 6-CF.sub.3 H Cl H Cl H white crystal 207-21031 CH O H H Cl H F F white crystal 199-20132 CH O H H Cl H Cl H white crystal 219-22133 CH O H H Cl H Cl Cl white crystal 246-24734 CH O 3-Cl 6-Cl H H Cl Cl white crystal above 26035 N O H H Cl Cl OCH.sub.3 OCH.sub.3 white crystal 238-24236 N O H H H H F Cl white crystal 220-22237 N O H H H H OCH.sub.3 OCH.sub.3 white crystal 223-22638 N O H H Cl Cl F Cl white crystal 238-24039 N S H H H H F Cl white crystal 199-20140 N S H H H H Cl H white crystal 217-22041 N S H H H H OCH.sub.3 OCH.sub.3 white crystal 236-23942 N O 6-Cl H H H OCH.sub.3 OCH.sub.3 white crystal 233-23643 N O 6-Cl H Cl H F Cl white crystal 120-12144 N O 6-Cl H Cl H OCH.sub.3 OCH.sub.3 white crystal 242-24445 N O 6-Cl H Cl Cl F Cl white crystal 217-21946 N O 6-Cl H Cl Cl OCH.sub.3 OCH.sub.3 white crystal 27247 N S 6-Cl H H H Cl H white crystal 220-22348 N S 6-Cl H H H Cl Cl white crystal 208-21049 N S 6-Cl H H H OCH.sub.3 OCH.sub.3 white crystal 216-22050 N O 6-F H H H F F white crystal 235-23851 N O 6-F H H H F Cl white crystal 220-22252 N O 6-F H H H Cl Cl white crystal 238-24153 N O 6-F H H H OCH.sub.3 OCH.sub.3 white crystal 229-23354 N O 6-F H Cl H F Cl white crystal 225-22755 N O 6-F H Cl Cl F Cl white crystal 220-22156 N O 6-F H Cl Cl OCH.sub.3 OCH.sub.3 white crystal 250-25157 N O 6-Cl 7-Cl Cl Cl F F white crystal above 30058 N O 6-Cl 7-Cl Cl Cl F Cl white crystal above 30059 N O 6-Cl 7-Cl Cl Cl Cl H white crystal above 30060 N O 6-Cl 7-Cl Cl Cl Cl Cl white crystal above 30061 N O 6-Cl 7-Cl Cl Cl OCH.sub.3 OCH.sub.3 white crystal above 30062 N O 6-CF.sub.3 H Cl Cl F F white crystal 240-24363 N O 6-CF.sub.3 H Cl Cl F Cl white crystal 240-24364 N O 6-NO.sub.2 H Cl Cl OCH.sub.3 OCH.sub.3 white crystal 238-24065 CH O H H Cl H OCH.sub.3 OCH.sub.3 white crystal 209-21166 CH O 6-Br H Cl Cl F F white crystal 230-23367 CH O 6-Br H Cl Cl Cl H white crystal 210-21368 CH O 6-Br H Cl Cl Cl Cl white crystal 271-274__________________________________________________________________________

Preparation of compounds represented by the following formula Ib: ##STR9##

TABLE 2__________________________________________________________________________CompoundNo A B X.sup.1 X.sup.2 R.sup.1 R.sup.2 R.sup.3 R.sup.4 Properties m.p. (.degree.C.)__________________________________________________________________________69 N O 6-Cl H H H Cl H white crystal 219-22170 N O 6-Cl H H H Cl Cl white crystal 190-19271 N O H H H H F F white crystal 203-20572 N O H H H H F Cl white crystal 195-19773 N O H H H H Cl H white crystal 196-19774 N O H H H H Cl Cl white crystal 190-19275 N O H H H H OCH.sub.3 OCH.sub.3 white crystal 182-18476 N O 6-F H H H F F white crystal 200-201.577 N O 6-F H H H F Cl white crystal 171-17378 N O 6-F H H H Cl H white crystal 215-21679 N O 6-F H H H Cl Cl white crystal 189- 19280 N O 6-F H H H OCH.sub.3 OCH.sub.3 white crystal 217-21881 N S 6-F H H H F F white crystal 219-22182 N S 6-F H H H F Cl white crystal 163-16583 N S 6-F H H H Cl H white crystal 210-21284 N S 6-F H H H Cl Cl white crystal 191-19385 N S 6-F H H H OCH.sub.3 OCH.sub.3 white crystal 202-20586 N O 6-Cl H H H F F white crystal 198-20187 N O 6-Cl H H H F Cl white crystal 178-18088 N O 6-Cl H H H OCH.sub.3 OCH.sub.3 white crystal 195-19889 N O 6-Cl H H Cl F F white crystal 235-23790 N O 6-Cl H H Cl F Cl white crystal 193-19591 N O 6-Cl H H Cl Cl H white crystal 210-21292 N O 6-Cl H H Cl Cl Cl white crystal 204-20693 N O 6-Cl H H Cl OCH.sub.3 OCH.sub.3 white crystal 208-21094 N O 6-Br H H H F Cl white crystal 188-19095 N O 6-CF.sub.3 H H H F F white crystal 199-20196 N O 6-CF.sub.3 H H H F Cl white crystal 186-18897 N O 6-CF.sub.3 H H H Cl Cl white crystal 192-19498 CH O H H H H F F white crystal 156-15899 CH O H H H H F Cl white crystal 161-163100 CH O H H H H Cl H white crystal 180-182101 CH 0 H H H H Cl Cl white crystal 180-182102 CH O H H H H OCH.sub.3 OCH.sub.3 white crystal 202-205103 CH O 6-Br H H H F F white crystal 202-203104 CH O 6-Br H H H F Cl white crystal 219-220105 CH O 6-Br H H H Cl H white crystal 203-204__________________________________________________________________________

Next, formulation examples of insecticides containing the compounds of this invention are illustrated below. In these examples, parts are by weight.

______________________________________Formulation 1 Emulsifiable concentrate:______________________________________compound of this invention 5 partsxylol 80 partsSorpol 2680 (a product of Toho 15 partsChem. Industrial Co., Ltd.)______________________________________

The above ingredients are uniformly mixed to obtain an emulsifiable concentrate. This emulsifiable concentrate is diluted with water to 50 times, and sprayed in a quantity of 25-50 ml/m.sup.2 or diluted with water to 1,000-2,000 times and sprayed in a quantity of 100-150 l/10 a.

______________________________________Formulation 2 oil-form:______________________________________compound of this invention 0.1 partpiperonyl butoxide 0.9 partwhite kerosene 99.0 parts______________________________________

The above ingredients are uniformly mixed to form an oil. This oil is applied in a quantity of 25-50 ml/m.sup.2 to ditches or pools.

______________________________________Formulation 3 wettable powder form:______________________________________compound of this invention 10 partsSiegreit (a product of Siegreit 75 partsMining Co.)Carplex (a product of Shionogi 10 parts& Co. Ltd.)Sorpol 8048 (a product of Toho 3 partsChem. Industrial Co., Ltd.)Runox 1000 (the same as above) 2 parts______________________________________

The above ingredients are uniformly mixed and ground to obtain a wettable powder. In use, the wettable powder is diluted with water to 500-2,000 times, and sprinkled in a quantity of 50-500 l/10 a.

______________________________________Formulation 4 dust-form:______________________________________compound of this invention 0.4 partpiperonyl butoxide 1.6 partstalc 98 parts______________________________________

The above ingredients are uniformly mixed to obtain a dust. This dust is scattered in a quantity of 15 g/m.sup.2 or 3-4 Kg/10 a.

______________________________________Formulation 5 granular form:______________________________________compound of this invention 5 partsbentonite 95 parts______________________________________

The above ingredients are uniformly mixed and ground. After addition of a small amount of water, the resulting mixture is thoroughly mixed, pelletized through an extrusion type pelletizer and dried to obtain granules. The granules are scattered as such, in a quantity of 3-4 Kg/10 a.

Next, excellent insecticidal action of the compounds of this invention is illustrated with reference to tests which are compared with controls using a commercially available product (diflubenzuron) represented by the following formula: ##STR10##

Test 1 killing test to Tobacco cutworm larvae:

Cabbage leaf pieces were immersed for about 10 sec. in a solution prepared by dispersing an active ingredient component compound into water and adjusting the concentration to a predetermined level. The cabbage leaf pieces were then picked up, dried in air and placed on a moistened filter paper in a Petri dish, 9 cm in diameter. Tobacco cutworm second instar larvae were set on the pieces, and after closing the dish with the cover, it was kept within a constant-temperature room at 25.degree. C. equipped with lights. Seven days after setting the larvae, the mortality was checked. The mortality was determined according to the formula: ##EQU1##

The results are shown in Table 3.

TABLE 3______________________________________ Mortality Concen. of effective ingredientTested Compound compound(compound No.) 10 ppm 1 ppm______________________________________control compound 90 20(diflubenzuron)4 100 1006 80 307 100 1009 100 8011 100 10012 100 10014 100 10015 100 10016 90 6017 100 7018 100 5019 80 4020 100 10022 100 10023 100 10024 100 10025 100 10028 60 3029 100 10030 100 5033 100 8035 100 10070 100 10036 100 4538 100 10039 100 10040 80 1043 100 10045 100 10051 100 10052 100 7054 100 10055 100 10057 100 10058 100 5059 100 3562 100 10063 100 10066 100 10067 100 10068 100 8576 100 9577 100 10079 100 8082 100 10083 90 2584 100 10086 100 10087 100 10089 100 5090 100 10091 100 10092 100 4094 100 10095 100 10096 100 10097 100 10099 100 70103 100 100104 100 100105 100 100______________________________________

Test 2 killing test for diamondback moth larvae

In the same manner as in Test 1, a wet filter paper was placed in a Petri dish. Cabbage leaf pieces treated with an agent solution were placed on the moistened filter paper and dried in air. Then, diamondback moth second instar larvae were set on the pieces. In the same manner as in Test 1, the % kill was determined seven days after setting the larvae. The results are shown in Table 4.

TABLE 4______________________________________ Mortality Concen. of effective ingredientTested Compound compound(compound No.) 1000 ppm 200 ppm______________________________________control compound 100 20(diflubenzuron)1 100 402 70 303 50 304 100 1006 70 407 100 1008 100 709 100 10010 100 5011 100 10012 100 5014 100 10015 100 10016 100 9017 100 10018 100 10019 100 8020 100 10021 70 3022 100 10023 100 10024 100 10025 100 10027 80 4029 100 10030 100 10031 100 8033 100 10034 90 3035 100 10070 100 10036 100 5038 100 9039 100 8040 100 10043 100 6545 100 7051 100 8552 100 4554 100 8555 100 9057 100 9058 100 5559 100 6062 100 10063 100 10066 100 10067 100 10068 100 9576 100 10077 100 10079 100 6082 100 7583 100 9584 100 4586 100 10087 100 10089 100 10090 100 10091 100 10092 100 10094 100 10095 100 10096 100 10097 100 9599 100 35103 100 100104 100 100105 100 80______________________________________

Test 3 Killing test to twenty-eight-spotted lady beetle larvae:

In the same manner as in Test 1, a wet filter paper was placed in a petri dish. Tomato leaf pieces treated with an agent solution were placed on the moistened filter paper and dried in air. Then, second instar larvae were set on the pieces. In the same manner as in Test 1, the % kill was determined seven days after setting the larvae. The results are shown in Table 5.

TABLE 5______________________________________ Mortality Concen. of effective ingredientTested Compound compound(compound No.) 30 ppm______________________________________control compound 100(diflubenzuron)49 10053 10098 100100 100101 100______________________________________

Claims

1. A heterocyclic ether or thioether linkage containing urea compound of the formula I: ##STR11## wherein A denotes nitrogen, X.sup.1 and X.sup.2 denote independently of each other hydrogen, halogen or trifluoromethyl, Y and Z denote independently of each other hydrogen or chlorine, and P and Q denote independently of each other hydrogen or halogen.

2. The heterocyclic ether or thioether linkage containing urea compound claimed in claim 1, having the formula: ##STR12## wherein A, X.sup.1 and Q have the same meanings given in claim 1 respectively and P denotes halogen.

3. The heterocyclic ether or thioether linkage containing urea compound claimed in claim 1, having the formula: ##STR13## wherein X.sup.1 denotes hydrogen, halogen or trifluoromethyl group, P and Q denote independently of each other hydrogen or halogen, and A and Z denote the same meanings given in claim 1.

4. The heterocyclic ether or thioether linkage containing urea compound of claim 1, having the formula: ##STR14## wherein X.sup.1 is hydrogen or halogen, Y and Z denote chlorine, P and Q denote halogen, and A denotes the same meanings given in claim 1.

5. The heterocyclic ether or thioether linkage containing urea compound of claim 4, having the formula: ##STR15##

6. The heterocyclic ether or thioether linkage containing urea compound of claim 4, having the formula: ##STR16##

7. The heterocyclic ether or thioether linkage containing urea compound of claim 4, having the formula: ##STR17##

8. A method for controlling insects, comprising administering an insecticidally effective amount of a compound having the formula: ##STR18## wherein B denotes oxygen or sulfur, A denotes nitrogen, X.sup.1 and X.sup.2 denote independently of each other hydrogen, halogen trifluoromethyl group or nitro group, Y and Z denote independently of each other hydrogen atom or halogen, and P and Q denote independently of each other hydrogen halogen, alkoxyl group or alkyl group.

9. The heterocyclic ether or thioether linkage containing urea compound as claimed in claim 3, wherein A, X.sup.1, Z and Q have the same meaning as in claim 3 and P denotes halogen.

10. The heterocyclic ether or thioether linkage containing urea compound of claim 3, having the formula: ##STR19##

11. The heterocyclic ether or thioether linkage containing urea compound of claim 3, having the formula: ##STR20##

12. The heterocyclic ether or thioether linkage containing urea compound of claim 3, having the formula: ##STR21##

13. The heterocyclic ether or thioether linkage containing urea compound of claim 3, having the formula: ##STR22##

14. The heterocyclic ether or thioether linkage containing urea compound of claim 3, having the formula: ##STR23##

15. The heterocyclic ether or thioether linkage containing urea compound of claim 3, having the formula: ##STR24##

16. The heterocyclic ether or thioether linkage containing urea compound of claim 3, having the formula: ##STR25##

17. The heterocyclic ether or thioether linkage containing urea compound of claim 3, having the formula: ##STR26##

18. An insecticidal composition which comprises an insecticidally effective amount of a compound of a heterocyclic ether or thioether linkage containing urea compound of the formula I according to claim 1, and an argicultural adjuvant in a form of a solution, a dispersion, an emulsifiable concentrate, an oil spray, a wettable powder, a dust, a granule, a tablet, a pellet, a paste or an aerosol.

19. The insecticidal composition according to claim 18, which further comprises piperonyl butoxide, octachlorodipropyl ether or N-octyl bicycloheptane dicarboxyimide.

20. The insecticidal composition according to claim 18, which further comprises an antioxidant.