HETEROCYCLIC COMPOUNDS AND FUNGIDICAL COMPOSITIONS

• Main Authors: RONALD PARRIS OWEN, WILLIAM DAVID WEIR, EDWARD ESSEX KILBOURN, HAROLD EDWIN CARLEY
• Format: Patent
• Language: English
• Published: 22.05.1975
• Subjects: AGRICULTURE; ANIMAL HUSBANDRY; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; CHEMISTRY; FISHING; FORESTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HUNTING; METALLURGY; ORGANIC CHEMISTRY; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS; PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTSTHEREOF; TRAPPING

1422430 3-Thioallophonic acid derivatives ROHM & HAAS CO 5 Dec 1973 [22 Jan 1973 (2)] 56309/73 Heading C2C Novel compounds have the Formula I wherein X is R1O- or R1S-, R1 being: (a) alkyl, straight or branched, of 1 to 12 carbon atoms, (b) alkyl or 1 to 12 carbon atoms substituted with halo, preferably chloro, or methoxy groups, (c) alkenyl of 2 to 12 carbon atoms, (d) alkynyl of 3 to 12 carbon atoms, (e) phenyl, (f) phenyl substituted with halo (preferably chloro) methyl, methoxy or nitro, (g) benzyl or (h) benzyl substituted in the ring with halo (preferably chloro) methyl, methoxy or nitro; Y is a heterocyclic radical having 5 or 6 cyclic atoms and having as a hetero atom O, S or N or any combination of two of these wherein the total number of hetero atoms is up to three and the acetoxymethyl, chloro, methyl or nitro substituted derivatives of these; R is hydrogen or methyl; Z is halo (preferably chloro) methyl, methoxy or nitro and n is 0 to 3. The compounds of Formula I are prepared by (A) reacting a compound of formula R-CO-Y with a compound of formula or (B) reacting a compound of formula with a compound of formula the use of a base being necessary in (A) or (B) when reactions of acid-sensitive aldehydes or their Schiff bases are involved. In particular, compounds of Formula VII wherein W is hydrogen, acetoxymethyl, chloro, methyl or nitro, are obtained by reacting a compound of formula with a compound of formula, X-CO-NCS in the presence of an inert solvent and 0À5-20 mole per cent based on the heterocyclic reactant of a tertiary amine whose dissociation constant at 25‹ C. is in the range of 5 Î 10-3 to 5 Î 10-5 (e.g. trimethylamine, triethylamine, tripropylamine, triisobutylamine, methyldiethylamine, tetramethylethylenediamine, N,N-dimethylethanolamine and dimethylaniline). Examples prepare compounds of Formula I wherein Y is 2-furyl optionally 5-substituted by CH 3 -, CH 3 CO.OCH 2 - or NO 2 groups, 2- thienyl optionally 5-substituted by chlorine, 2-pyrryl, 2-(N-methyl)pyrryl, 5-isothiazolyl or 2-pyridyl. Other specified heterocyclic radicals Y are thiazolyl, imidazolyl, isoxazolyl, oxadiazolyl, oxazolyl, pyrimidyl, thiadiazolyl, triazinyl and triazolyl. The compounds of Formula I (and VII) are fungicides and show anthelmintic activity.