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filingDate 1973-05-01-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1976-06-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber IL-42161-A
titleOfInvention Organophosphorated isothiazole derivatives and preparation process
abstract 1397882 Pesticidal phosphorus-containing isothiazole derivatives ROUSSEL-UCLAF 17 May 1973 [17 May 1972] 23510/73 Headings C2P and C2C Novel compounds of Formula I where R 1 is C 1-3 alkyl or alkoxy, amino or mono- or di-(C 1-3 alkyl)amino, R 2 is C 1-3 alkyl, R 3 is H, C 1-5 alkyl, C 6-10 aryl, C 7-12 aralkyl, CN, C 2-4 alkoxycarbonyl, amino or mono- (C 6-10 aryl) amino, R 4 is CN, C 1-4 alkylthio, alkylsulphinyl or alkylsulphonyl, carbamoyl, C 2-4 alkoxycarbonyl, sulphamoyl, or mono- or di-(C 1-3 alkyl)sulphamoyl and X is O or S; may be prepared by reacting a compound of Formula II or an alkali metal salt thereof with a compound of Formula III where Hal is Cl or Br. Starting materials of Formula II are prepared in preparations I to III as follows: (a) 3- hydroxy - 4 - cyano - 5 - methyl - isothiazole is prepared by reacting the sodium salt of 1,1- dicyano-2-mercapto-1-propene with hydrogen peroxide; (b) 3-hydroxy-4-cyano-5-phenyl-isothiazole is prepared by heating the corresponding 3-methoxy compound with HBr in acetic acid; (c) 3-hydroxy-4-cyano-5-n-butyl-isothiazole is prepared by reacting valeronitrile with ethyl mercaptan and HCl to give 1-ethylthio-1- pentanimine, reacting this with H 2 S to give ethyl dithiovalerate, reacting this with malononitrile to give the potassium salt of 3-mercapto- 2-cyano-2-heptenonitrile and reacting this with hydrogen peroxide; and (d) 3-hydroxy-4-carbamoyl-5-methyl-isothiazole is prepared by reacting the corresponding 4-cyano compound with concentrated sulphuric acid. The compounds of Formula I have insecticidal and acaricidal properties and may be used as the active ingredients in conventional pesticidal compositions.n[GB1397882A]
priorityDate 1972-05-17-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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