GB1103404A - New fungicidal materials - Google Patents

Abstract

The invention comprises bicycloheptane derivatives and bicycloheptene derivatives having the formula <FORM:1103404/C2/1> wherein R1 represents a C1 or C2 alkyleneoxy radical or a single bond, and R2 represents a chloroalkyl radical of formula CCl3 or CnHpClm, wherein n, m and p are positive integers and p + m = 2n + 1, n being 1 to 6 and m being 3 to 7, and wherein R1 is <FORM:1103404/C2/2> <FORM:1103404/C2/3> in which X is a hydrogen or chlorine atom and Y is a hydrogen or chlorine atom or a methyl group, with the proviso that, when R2 is CCl3, R1 is not <FORM:1103404/C2/4> The compounds may be prepared according to the reactions <FORM:1103404/C2/5> or <FORM:1103404/C2/6>ALSO:Fungicidal compositions comprise a compound of formula: <FORM:1103404/A5-A6/1> wherein R1 represents a C1 or C2 alkyleneoxy radical or a single bond, and R2 represents a chloroalkyl radical of formula CCl3 or CnHpClm wherein n, m and p are positive integers and p + m=2n + 1, n being 1 to 6 and m being 3 to 7, and wherein R\sv is <FORM:1103404/A5-A6/2> or <FORM:1103404/A5-A6/3> in which X is a hydrogen or chlorine atom and Y is a hydrogen or chlorine atom or a methyl group, with the proviso that, when R2 is CCl3, R\sv is not <FORM:1103404/A5-A6/4> The compositions may contain one or more solid carriers (such as clay, talc, diatomite or vermiculite), one or more liquid carriers (such as methanol or xylol) or one or more gaseous carriers (such as air or a fluorinated hydrocarbon known under the registered Trade Mark "Freon"). The compositions may also contain auxiliary agents (such as surfactants, suspending agents and emulsifiers) and other unspecified active components (such as insecticides, fungicides, herbicides, soil conditioners and fertilizers). In the examples, dusts, wettable powders and emulsifiable concentrates are described in which the fungicidal compounds are N-thiotrichloromethyl-bicyclo (2,2,1) heptane-2,3- dicarboxylic acid imide; N-thiotrichloromethyl-bicyclo (2,2,1) 5-methyl heptane-2,3- dicarboxylic acid imide; N-(O-trichloromethylthio-2-oxyethyl)-bicyclo (2,2,1) heptane-2,3-dicarboxylic acid imide; N-thio-1,2,2,2-tetrachloroethyl-bicyclo (2,2,1) 5-heptene-2,3-dicarboxylic acid imide; N-thio-1,2,2,2-tetrachloroethyl-bicyclo (2,2,1) 5-methyl-5-heptene-2,3-dicarboxylic acid imide; N-thio-1,2,2,3,3,3-hexachloropropyl-bicyclo (2,2,1) 5-heptene-2,3-dicarboxylic acid imide; N-thio-1,2,2,2-tetrachloroethyl-bicyclo (2,2,1) heptane-2,3-dicarboxylic acid imide; N-thio-1,2,2,2-tetrachloroethyl-bicyclo (2,2,1) 5-methylheptane-2,3-dicarboxylic acid imide; or N-thio-1,2,2,3,3,3-hexachloropropyl-bicyclo (2,2,1) heptane-2,3-dicarboxylic acid imide. The compositions exhibit strong fungicidal activity against plant pathogenic microorganisms and provide a protection against plant diseases.