公开(公告)号：JPS6084262A

公开(公告)日：1985-05-13

申请号：JP19206183

申请日：1983-10-14

Applicant: KUMIAI CHEMICAL INDUSTRY CO ,  IHARA CHEMICAL IND CO

Inventor： TADA OSAMU ,  SUGAYA MASASHI ,  NOMURA YASUO ,  HORII TETSUO ,  INAMORI MASAHITO ,  SHIMAZAKI ISAO

IPC: A01N47/42 ,  C07C67/00 ,  C07C325/00 ,  C07C335/38

Abstract: NEW MATERIAL:The compound of formula I (X is Cl or F; Y is H or F; R is alkyl or alkenyl; Z -Z are H, Cl or trifluoromethyl). EXAMPLE:N-(2-Chlorobenzoyl)-N'-(3,5-dichlorophenyl)-S allylisothiourea. USE:Insectcide capable of effectively controlling vermin at a low concentration. PREPARATION:The compound of formula I can be produced by reacting the N-benzoyl-N'-phenylthiourea derivative of formula II with the halide of formula R-X (X is halogen) in the presence of an acid acceptor. The solvent used in the above reaction is e.g. benzene, toluene, etc. and the acid acceptor is e.g. NaOH, KOH, etc.

公开(公告)号：JPS5948807B2

公开(公告)日：1984-11-29

申请号：JP1904178

申请日：1978-02-23

Applicant: Kumiai Chemical Industry Co

Inventor： HIRANO TADAMI ,  TADA OSAMU ,  MINOWA MASAO

IPC: A01N57/16 ,  A01N41/04

公开(公告)号：JPS5673090A

公开(公告)日：1981-06-17

申请号：JP14970679

申请日：1979-11-19

Applicant: KUMIAI CHEMICAL INDUSTRY CO

Inventor： CHIYOMARU ISAO ,  HORII TETSUO ,  NITSUTA KOYATA ,  TAKAYAMA SHIYUUICHI ,  HIRANO TADAMI ,  OGAWA ATSUKI ,  TADA OSAMU

IPC: A01N57/14 ,  C07F9/165 ,  C07F9/18

Abstract: NEW MATERIAL:An organic phosphate derivative of formula I (R and R' are alkyl). EXAMPLE:O-Methyl S-n-propyl O-4-(4-trifluoromethylphenoxy)phenyl dithiophosphate. USE:An insecticide, acaricide and nematocide, having a wide insecticidal spectrum, and capable of controlling various crops simultaneously with improved lasting effects without phytotoxicity to crops, e.g. rice plants, vegetables, green tea and cotton, with low toxicity to men, cattle, fishes and shellfishes, and having great safety, etc. PROCESS:A compound of formula II (X is halogen) is reacted with a compound of formula III to give the titled compound to formula I. The reaction is preferably carried out in the presence of an acid acceptor, e.g. a trialkylamine, pyridine or dialkylaniline, and a solvent, e.g. an ether, amide or alcohol alone or in a mixture thereof.

公开(公告)号：JPS5612398A

公开(公告)日：1981-02-06

申请号：JP8791579

申请日：1979-07-11

Applicant: KUMIAI CHEMICAL INDUSTRY CO

Inventor： FUJIMORI KUNIHIKO ,  NITSUTA KOYATA ,  SUGIYAMA HIDETOSHI ,  CHIYOMARU ISAO ,  HIRANO TADAMI ,  TADA OSAMU

IPC: A01N57/14 ,  C07F9/18

Abstract: NEW MATERIAL:An organic phosphate derivative expressed by formula I (R and R' are alkyl groups; X is H, halogen alkyl, alkoxy, alkylthio, cyano or trifluoromethyl group). EXAMPLE:O-Ethyl O-(2-benzyloxyphenyl) S-n-propyl phosphorothiolate of formula II. USE:A germicide, insecticide, and acaricide against injurious insects, mites and sanitary injurious insects and blast of a rice plant. PROCESS:An O-alkyl S-alkylthiolphosphoric acid halide is reacted with a benzyloxyphenol of formula III in the presence of a solvent and a tertiary amine as an acid acceptor at -10-50 deg.C for 1-20hr.

公开(公告)号：JP2000198768A

公开(公告)日：2000-07-18

申请号：JP10890399

申请日：1999-04-16

Applicant: KUMIAI CHEMICAL INDUSTRY CO ,  IHARA CHEMICAL IND CO

Inventor： TOYABE KEIJI ,  TAKETO NOBUO ,  ITO MINORU ,  HIRAIDE TETSUYA ,  NISHIYAMA KIYOTOSHI ,  ASAHIDA MITSUHARU ,  MAEDA YASUNOBU ,  WADA NOBUHIDE ,  FUJISAWA TOYOICHI ,  YANO YUKO ,  KOMATSU MASAAKI ,  TADA OSAMU

IPC: C07D249/08 ,  A01N41/10 ,  A01N43/08 ,  A01N43/10 ,  A01N43/40 ,  A01N43/54 ,  A01N43/56 ,  A01N43/653 ,  A01N43/76 ,  A01N43/78 ,  C07C317/14 ,  C07C317/22 ,  C07C317/44 ,  C07C321/28 ,  C07C323/09 ,  C07C323/18 ,  C07C323/22 ,  C07C323/35 ,  C07C323/41 ,  C07C323/43 ,  C07C323/62 ,  C07D213/57 ,  C07D231/12 ,  C07D239/36 ,  C07D333/20 ,  C07D333/28

Abstract: PROBLEM TO BE SOLVED: To obtain the subject new compound as a specific arylphenyl sulfide derivative, having high efficacy even at low doses, useful as an insecticide of high safety, exhibiting excellent controlling effect on insect pests including hemipteron pests, and capable of controlling resistant insect pests as well. SOLUTION: This new compound is a compound of formula I R is a 2-6C alkyl, alkenyl, or the like; (n) is 0-2; Ar is a group of formula II [Q1 to Q5 are each N, C-A1 (A1 is H, a halogen, or the like) or the like]; B0 to B3 are each H, a halogen, or the like}, e.g. 2-(2-propenylthio)-4-(4-trifluoromethylphenyl) benzonitrile. The compound of formula I is obtained by reaction of an arylphenylthiol derivative with a compound of RL1 (L1 is a halogen or the like) in the molar ratio of the latter to the former of 1-5 in 0.5-10 l of a solvent (e.g. diethyl ether) in the presence of 1-5 molar times of a base or radical initiator pref. at 0-150 deg.C for 10 min to 20 h.

公开(公告)号：JPS6248676B2

公开(公告)日：1987-10-15

申请号：JP14266480

申请日：1980-10-13

Applicant: KUMIAI CHEMICAL INDUSTRY CO

Inventor： CHOMARU ISAO ,  SUGYAMA HIDETOSHI ,  NITSUTA YASUYATA ,  FUJIMORI KUNIHIKO ,  HIRANO TADAMI ,  TADA OSAMU

IPC: A01N57/16 ,  C07F9/165 ,  C07F9/18 ,  C07F9/655

公开(公告)号：JPS6051163A

公开(公告)日：1985-03-22

申请号：JP16015083

申请日：1983-08-31

Applicant: KUMIAI CHEMICAL INDUSTRY CO ,  IHARA CHEMICAL IND CO

Inventor： TADA OSAMU ,  SUGAYA MASASHI ,  NOMURA YASUO ,  HORII TETSUO ,  INAMORI MASAHITO ,  SHIMAZAKI ISAO

IPC: A01N47/34 ,  C07C67/00 ,  C07C239/00 ,  C07C275/54

Abstract: NEW MATERIAL:The compound of formula I (R is H or halogen; R is halogen; R is H, halogen or trifluoromethyl; R is H or halogen; R is H or lower alkyl; R is halogen, nitro or trifluoromethyl; n is 0-2). EXAMPLE:N-(2,6-Difluorobenzoyl)-N'-[4-(3,5-dichloroanilino)phenyl]urea. USE:Insecticide and miticide. It exhibits excellent insecticidal activity especially against diamondback moth and night crawler. PREPARATION:The compound of formula I can be produced by reacting the benzoyl isocyanate derivative of formula II with the aniline derivative of formula III optionally in a solvent (e.g. toluene, chloroform, etc.) at 0-150 deg.C for 10min-5hr.

公开(公告)号：JPS58154592A

公开(公告)日：1983-09-14

申请号：JP3587582

申请日：1982-03-09

Applicant: KUMIAI CHEMICAL INDUSTRY CO

Inventor： NISHIMURA TATSUMI ,  HORII TETSUO ,  HIRANO TADAMI ,  TADA OSAMU

IPC: A01N57/10 ,  C07F9/165

Abstract: NEW MATERIAL:The compound of formulaI R and R are lower alkyl; R is >=6C alkyl or group of formula II (X is halogen) . EXAMPLE:The compound of formula III. USE:An isecticidal and miticidal agent for the vermin of paddy field, plowed land, tea field, orchard, cotton field, and mites, etc. PROCESS:The objective compound is prepared by reacting the compound of formula IV (Y is halogen) (e.g. O-ethyl-S-n-propylchlorido-phospholothiolate) with the compound of formula V (2,2,2-trichloro-1-n-heptylthioethanol, etc.) in a solvent such as benzene in the presence of an acid acceptor such as triethylamine.

公开(公告)号：JPS56110694A

公开(公告)日：1981-09-01

申请号：JP1344380

申请日：1980-02-06

Applicant: KUMIAI CHEMICAL INDUSTRY CO

Inventor： TAKAYAMA SHIYUUICHI ,  CHIYOMARU ISAO ,  INOUE SHIYUUJI ,  HIRANO TADAMI ,  TADA OSAMU

IPC: C07F9/18 ,  A01N57/14

Abstract: NEW MATERIAL:O-( 4-Bromo-2- chlorophenyl )0-methyl S-normalpropylphosphoro thioate shown by the formula I. USE:A fungicide, insecticide, acaricide, and nematocide. Having high controlling effects against various noxious insects, acarids, sanitary noxious insects, nematodes damaging agricultural and gardening crops, and blast of rice plant. Having excellent effects against Corposina niponensis, the improtant noxious insect of apple. Having no phytotoxicity. Having a wide insect-killing spectrum, the compound is capable of destroying noxious insects simultaneously in plants, e.g., vegetables, etc. so that it eliminates labor and is economical. PROCESS:An O-methyl S-normalpropylthiolphosphoric acid halide shown by the formula II (X is halogen) is reacted with 4-bromo 2-chlorophenol shown by the formula III in the presence of a base (dehydrohalogenating agent) in a solvent, e.g., henzene, at -5-100 deg.C for 1-6hr, to give a compound shown by the formula I in high yield.

公开(公告)号：JPS54113437A

公开(公告)日：1979-09-05

申请号：JP1904178

申请日：1978-02-23

Applicant: KUMIAI CHEMICAL INDUSTRY CO

Inventor： HIRANO TADAMI ,  TADA OSAMU ,  MINOWA MASAO

IPC: A01N57/16 ,  A01N41/04

Abstract: PURPOSE:To provide a miticidal and insecticidal composition containing a dithiophophoric acid ester and a sulfonic acid ester as effective components. CONSTITUTION:Composition containing (A) dithiophosphoric acid S-[(2-methoxy- 5-oxy-1,3,4-thiadiazolin-4-yl)methyl]-O,O-dimethyl ester and (B) p-chlorophenylbenzenesulfonic acid p-chlorophenyl ester as effective component. The weight ratio of (A) to (B) is 1:5 - 5:1. EFFECT:Synergistic effect to mites and noxious insects.