METODO PARA PREPARAR UNA COMPOSICION BIOCIDA.

摘要

1287899 1,2,4-Triazole derivatives ROHM & HAAS CO 4 Sept 1969 [4 Sept 1968 3 July 1969] 43799/69 Heading C2C Novel pesticidal compounds have Formula XII, XIII or XIV below, or are a tautomer or tautomer derivative of such compounds in which the tautomer or tautomer derivative is of Formula III, V or VA given hereinbelow, or are acid salts of any such compounds wherein A is (a) hydrogen, (b) C 1 -C 5 alkyl or C 1 -C 5 alkyl substituted by (1) halogen, C 1 -C 5 alkoxy, cyano, hydroxy, or nitro; (2) aryloxy or alkoxy-, alkyl-, halo-, or nitro-substituted aryloxy; (3) aryl or alkoxy-, alkyl-, halo- or nitro-substituted aryl; or (4) benzoyl or halo-, alkoxy-, alkyl- or nitro-substituted benzoyl; (c) the group -C(X)R4 wherein X is O or S and R4 is aryl or C 1 -C 5 alkyl-substituted aryl, C 1 -C 5 alkoxy-substituted aryl, halo- or nitrosubstituted aryl, furyl or the group -NR5R6 wherein R5 and R6 are hydrogen or C 1 -C 5 alkyl; (d) the group -CH 2 C(O)NR5R6 wherein R5 and R6 are as defined above; (e) the group -CH(OH)R7 wherein R7 is hydrogen, C 1 -C 5 alkyl or halo-substituted C 1 -C 5 alkyl; (f) the group wherein C and D each represent hydrogen or a meta-directing group with the proviso that only one of C and D may be hydrogen; or (g) a saltforming metal; when A is hydrogen, R8 is C 3 -C 18 alkyl which may be substituted with one or more halo, C 1 -C 5 alkoxy, hydroxy or nitro groups; or C 3 -C 8 cycloalkyl which may be substituted with one or more halo, hydroxy or nitro groups; when A is methyl, R8 is C 3 -C 18 alkyl which may be substituted with one or more halo, C 1 -C 5 alkoxy, hydroxy or nitro groups; aralkyl of up to 10 carbon atoms; or aralkyl of up to 10 carbon atoms in which the aryl group is substituted with C 1 -C 5 alkyl, halo or nitro groups; when A is carbamoylmethyl, benzyl, nitrobenzyl or sodium, R8 is C 1 -C 18 alkyl which may be substituted with one or more halo, C 1 -C 5 alkoxy, hydroxy or nitro groups; aralkyl of up to 10 carbon atoms; or aralkyl of up to 10 carbon atoms in which the aryl group is substituted with C 1 -C 5 alkyl, halo or nitro groups; when A is all other values, R8 is C 1 - C 18 alkyl which may be substituted with one or more halo, C 1 -C 5 alkoxy, hydroxy or nitro groups; C 3 -C 8 cycloalkyl which may be substituted with one or more halo, hydroxy or nitro groups; aralkyl of up to 10 carbon atoms; aralkyl of up to 10 carbon atoms substituted in the aryl group with C 1 -C 8 alkyl, halo or nitro groups; aryl; or C 1 -C 5 alkyl-, halo- or nitrosubstituted aryl; and R9 is hydrogen; C 1 -C 18 alkyl which may be substituted with one or more halo, C 1 -C 5 alkoxy, hydroxy or nitro groups; furyl; or the group -COOB wherein B is hydrogen, C 1 -C 12 alkyl, ammonium, ammonium monosubstituted with C 1 -C 5 alkyl or C 1 -C 5 hydroxyalkyl, ammonium disubstituted with C 1 -C 5 alkyl or C 1 -C 5 hydroxyalkyl, ammonium trisubstituted with C 1 -C 5 alkyl or C 1 -C 5 hydroxyalkyl, quaternary ammonium or a salt-forming metal; R10 is C 3 -C 18 alkyl exclusive of the n-butyl group; and R11 is C 2 -C 18 alkyl which may be substituted with one or more halo, alkoxy, hydroxy, or nitro groups, or C 3 -C 8 cycloalkyl, exclusive of unsubstituted cyclohexyl, but which may be substituted with one or more halo, hydroxy or nitro groups. Preparative methods include: (1) for compounds of Formula XIII, the reaction of N,N-dimethylformamide or diformhydrazide with R10NH 2 or the oxidative removal of SH from 3-mercaptotriazoles; (2) alkaline cyclization of R9CONHNHCSNHR8; (3) reaction of R8NHCSNHNH 2 with R9COOEt or HOCOOEt in the presence of an alkali metal alkoxide; (4) decarboxylation of 1,2,4-triazoles in which R9 is COOH; (5) conversion of compounds in which A is H to compounds in which A has other values, e.g. by reaction with A-hal, R5NCO, R5NCS (giving A as -CONHR5 or -CSNHR5) or an olefinic nitrile (where A is cyanoalkyl), the last process tending to give isomers of Formula V; (6) standard methods of salt formation. Intermediates prepared are from 4-n-butylthio-semicarbazide and ethyl formate; by reaction of 4-cyclohexylthiosemicarbazide and formic acid; 1-(2-furoyl)-4-methylthiosemicarbazide from 4-methylthiosemicarbazide and furoyl chloride; and from diethyl oxalate, hydrazine hydrate and n-butyl isothiocyanate.