Patent EA-000623-B1 (EA)
Title: Substituted benzothiazoles as crop protection agents
Inventor: HEISTRACHTER ELISABETH
IPC: C07D417/04
Filed: 1996-08-26
Abstract: 1. A substituted benzothiazoles of the formula (I)   where X<1> and X<2> are independently of one another, are each oxygen of sulfur; R<1> is hydrogen, amino, C1-C6 alkyl or C1-C6 halogenalkyl; R<2> is hydrogen, halogen, C1-C6 alkyl or C1-C6 halogenalkyl, C1-C6 alkythio, C1-C6 alkylsulfenyl or C1-C6; R<3> is hydrogen, halogen, C1-C6 alkyl; R4 is hydrogen, halogen; R<5> is cyano, halogen, C1-C6 alkyl, C1-C6 halogenalkyl, C1-C6 alkoxy or C1-C6 halogenalkoxy; Y is a chemical bond, oxigen or sulfur, -SO- or -SO2-; R6 is hydrogen, cyano, halogen, C3-C6 cycloalkyl, C1-C6 alkyl halide, C3-C6 alkenyl, C3-C6 alkyl halide, C3-C6 alkinyl or C1-C6 alkyl, wherein the said cycloalkyl, alkyl, alkenyl and alkinyl groups can be substituted by cyano C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, C1-C6 alkylcarbonyloxy, C1-C6 alkoxy halide, C1-C6 alkylthio halide or C3-C6 cycloalkyl, provided that R<6> may be cyano only when Y is a chemical bond, oxygen or sulphur, and R<6> may be halogen only when Y is a chemical bond. 2. An enaminoester of the formula IV   where L<2> is C1-C6 alkyl or phenyl, and variables R<1>-R<6> and Y have values as defined in Claim 1. 3. An enaminocarboxylate of the formula V   where L<2> is C1-C6 alkyl or phenyl, and variables R<1>-R<6> and Y have values as defined in Claim 1. 4. An isocyanate of the formula XI   where Y is -SO- or -SO2 and variables R<4>-R<6> have values as defined in Claim 1. 5. An aniline derivative of the formula XIV   where Y is -SO- or -SO2 and variables R<4>-R<6> have values as defined in Claim 1. 6. A herbicide containing a herbicidal amount of at least one substituted benzothiazole of the formula I or of an agriculturally useful salt of I, as claimed in Claim 1, and at least one inert liquid or solid carrier and, if desired, at least one surfactant. 7. A plant desiccant or defoliant containing an amount, effective for desiccation or defoliation, of at least one substituted benzothiazole of the formula I or of an agriculturally useful salt of I, as claimed in Claim 1, and at least one inert liquid or solid carrier and, if desired, at least one surfactant. 8. A method for controlling undesirable plant growth, wherein a herbicidal amount of at least one substituted benzothiazole of the formula I or of an agriculturally useful salt of I, as claimed in Claim 1, is allowed to act on plants, on their habitat or on seed. 9. A method for desiccating or defoliating plants, wherein an amount, effective for desiccation or defoliation, of at least one substituted benzothiazole of the formula I or of an agriculturally useful salt of I, as claimed in Claim 1, is allowed to act on plants. 10. A process for the preparation of a substituted benzothiazole of the formula I as claimed in Claim 1, wherein either a) a substituted benzothiazole of the formula I where R<1> is hydrogen and X<1> is oxygen   is alkylated or aminated, or b) a substituted benzothiazole of the formula I where X<2> is oxygen   is treated with a sulfurizing reagent, or c) a substituted benzothiazole of the formula I, in which YR<6> is chlorine, bromine, -SO2-alkyl or -SO2-haloalkyl, is reacted with an alcohol HOR<6> or mercaptan HSR<6>, or d) a substituted benzothiazole of the formula I where X<1> and X<2> are each oxygen and Y is sulfur or -SO-,   is oxidized, or d) an enaminoester of the formula IV   or an enaminocarboxylate of the formula V   is cyclized, or f) a 2-aminobenzothiazole of the formula VI   is diazotized and the product is subjected to a Sandmeyer reaction or a variant thereof.