Takeda Chemical Industries, Inc.

Nippon Chemical Industrial Co., Ltd.

Yasuo Sato

Yoshiyuki Okada

Kazuo Konishi

Hiroshi Nagase

Tetsuo Okauchi

Kentaro Hiraga

Nobuo Matsumoto

Takashi Kuragano

Kazuo Kamei

Hiroyuki Mitsudera

Toshiya Kamikado

Masayoshi Nagano

This invention relates to a benzoylurea derivative of the formula: ##STR1## wherein X.sup.1 and X.sup.2 are hydrogen, halogen, alkyl or alkoxy; and one of Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4 and Y.sup.5 is halogenoalkylsulfinyl or halogenoalkylsulfonyl, and the others are hydrogen, halogen or alkyl, exhibiting excellent insecticidal and ovicidal activities (particularly, molt inhibitory activity), their production and use.

Benzoylureas, their production and use

Organic phosphates of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are respectively an alkyl group; R.sup.3 is a phenyl group which is substituted at least by a pyridazinyloxy or pyridazinylthio group in which the pyridazinyl group may be substituted; and X is an oxygen or sulfur atom, or a salt thereof, have marked insecticidal-acaricidal activity against plant pests and mites, household pests, with very low toxicity to warm-blooded animals and fish.

Pyridazinyloxy (or thio) phenyl phosphates

A novel 1,3-dithiane of the formula ##STR1## wherein R.sup.1 is a di-substituted amino group; R.sup.2 and R.sup.3 are such that one of them is an electron-withdrawing group with the other being a hydrogen atom, a hydrocarbon group or heterocyclic group of the class consisting of thienyl, triazolyl, and pyridyl, which may optionally be substituted or that R.sup.2 and R.sup.3 taken together with the adjacent carbon atom form a spiro ring provided that at least one of R.sup.2 and R.sup.3 is a carbonyl group; X.sup.1 and X.sup.2 each is a sulfur atom and at least one of X.sup.1 and X.sup.2 may be oxidized, or a salt thereof, possesses very useful pesticidal actions.

Insecticidally, acaricidally, and nematocidally 2-amino-1,3-dithiane

New insecticidal or/and ovicidal benzoylurea derivatives of the formula: ##STR1## wherein X.sup.1 is hydrogen or halogen; X.sup.2 is halogen; Y.sup.1, Y.sup.2 and Y.sup.3 are hydrogen, halogen or alkyl, whereby at least one of Y.sup.1, Y.sup.2 and Y.sup.3 is other than hydrogen; and R is hydrogen or a group represented by the formula --CF.sub.a Z.sub.b H.sub.(3-a-b) wherein a and b are 0, 1, 2 or 3, with a+b.ltoreq.3 and Z is halogen, their production and use.

Thiophenylureas, their production and use

A compound of the formula: ##STR1## wherein Y is alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, a halogen atom, nitro or trifluoromethyl; and n is an integer of 1, 2 or 3; and when n is 2, Y.sub.n may be an alkylidenedioxy group; or a salt thereof. These compounds are useful in producing pyrazol-4-yl phosphates which posess insecticidal-acaricidal activity.

1-phenyl-4-hydroxypyrazole derivatives

A urea derivative of the general formula, ##STR1## (wherein X is a halogen), which has higher insecticidal activity than known similar compounds, with lowered toxicity to mammals and fishes. The derivative can be produced by reacting 2-fluoro-4-haloaniline with 2,6-difluorobenzoyl isocyanate or reacting 2-fluoro-4-halo-phenylisocyanate with 2,6-difluorobenzamide.

N-(2,6-Difluorobenzoyl-N-'-(2-fluoro-4-halophenyl)urea

Pyrazol-4-yl phosphates of the formula ##STR1## wherein R.sup.1 represents a lower alkyl group, R.sup.2 is a lower alkoxy group or a lower alkylthio group, R.sup.3 represents hydrogen or a lower alkoxycarbonyl group, X is oxygen or sulfur atom, Y represents a lower alkyl, a lower alkoxy or a lower alkylthio group, a halogen atom, nitro or trifluoromethyl, and n is zero or an integer of 1, 2 or 3, or Yn represents an alkylidenedioxy containing 1 to 3 carbon atoms, have marked insecticidal-acaricidal activity against household pests, plant pests, mites, etc. without substantial toxicity to warm-blooded animals and fishes.

Pyrazol-4-yl phosphates and insecticidal and acaricidal use

Pyrazolyl phosphates of the formula ##STR1## wherein R.sup.1 is alkyl, aralkyl, or phenyl which may optionally be substituted by halogen or lower alkyl; R.sup.2 is hydrogen or lower alkyl; R.sup.3 is hydrogen, halogen, nitro, lower alkyl or --COOR.sup.6 wherein R.sup.6 is lower alkyl; R.sup.4 is lower alkyl; R.sup.5 is lower alkylthio; and X is oxygen or sulfur, have marked insecticidal-acaricidal activity against household pests, plant pests and mites, without substantial toxicity to warm-blooded animals and fish.

Insecticidal pyrazolyl phosphates

Novel acaricidal agents which contains, as an active ingredient, a pyrroline derivative of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each hydrogen, halogen or lower alkyl;

Acaricidal agents

Organophosphates of the formula: ##STR1## wherein n means zero or an integer of 1 or 2, are new compounds having very good pesticidal activities against insects, mites, ticks and other pests without substantial toxicity to warm-blooded animals, fish and plants.

O-Ethyl S-n-propyl O-[4-methylthio(sulfinyl)(sulfonyl)-2(3)-methoxyphenyl]

New miticidal compounds of the formula ##SPC1## Wherein R represents lower alkyl or lower alkenyl, R.sup.1 and R.sup. 2 respectively represent lower alkyl and X represents oxygen or sulfur.

Growing community of inventors

Kyoto, Japan

Yasuo Sato