GB1018308A - Novel dichlorophenyl-substituted amides,thioamides,imidates and amidines,and herbicidal compositions containing them - Google Patents

Abstract

The invention comprises compounds of formula Y-CH2-(CHR)n-Z and hydrohalides and hydrates thereof, wherein n is 0 or 1; when n is O, Y is 2,4- or 2,6-dichlorophenyl and Z is -CONR1R2, -CSNR1R2, -C(=NH)OR3 or -C(=NH)NR3R4, while when n is 1, Y is 2,6-dichlorophenyl and Z is -CONR1R2 or -CSNR1R2, R1 is alkyl, alkenyl, aryl or -CH2CO2H, R2 is H, alkyl, alkenyl or aryl, or R1 and R4 with the N form a heterocyclic ring; R3 and R4 are C1-3 alkyl or R4 may be H, and R is H, phenyl or -CONR3R4. The amides are prepared by reacting the appropriate amine and dichlorophenyl-substituted acid chloride under anyydrous conditions except where R1 is CH2CO2H, when the reaction with amido-acid is conducted in presence of aqueous alkali followed by acidification; an alternative method where R is phenyl and n is 1 is to react an alkali metal derivative of RCH2CONR1R2 with YCH2Cl. The thioamides are prepared by reacting the amides with P2S5 in presence of an inert organic solvent. The imidates are prepared by reacting the dichlorobenzyl cyanide with the alkanol in presence of hydrogen halide under anhydrous conditions and optionally treating the hydrohalide with a base. The amidines are prepared by reacting the imidates with the appropriate amine and optionally treating the hydrohalide with a base.ALSO:A method of eradicating weeds from crop areas comprises applying thereto a compound of formula Y-CH2-(CHR)n-Z (or a hydrohalide or hydrate thereof), n being 0 or 1, when n is 0, Y is 2, 4-or 2, 6-dichlorophenyl and Z is -CONR1R2, -CSNR1R2,-C(=NH)OR3 or-C(=NH)NR3R4, while when n is 1, Y is 2, 6-dichlorophenyl and Z is -CONR1R2 or -CSNR1R2, R1 is alkyl, alkenyl, aryl or -CH2CO2H, R2 is H, alkyl, alkenyl or aryl, or R1 and R2 with the N form a heterocyclic ring; R3 and R4 are C1-3 alkyl or R4 may be H, and R is H, phenyl or -CONR3R4. The compound may be applied as a composition, e.g. a dust, wettable powder, solution in an organic solvent, emulsifiable concentrate, aqueous emulsion or dispersion or one in the form of granules or pellets.