5-acyl-1-aryl-1,4-dihydro-4-oxo-3-carboxypyridazines and...

C - Chemistry – Metallurgy – 07 – C

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260/264.1, 71/7.

C07C 237/24 (2006.01) A01H 1/02 (2006.01) A01N 43/58 (2006.01) C07C 403/06 (2006.01) C07D 237/24 (2006.01)

Patent

CA 1276149

ABSTRACT OF THE DISCLOSURE This invention relates to a compound having the formula: Image wherein R1 is unsubstituted (C6-C10)aryl or (C6-C10)aryl substituted with up to three substituents selected from halogen, (C1-C4)alkyl, (C1-C4)alkoxy, trihalomethyl, nitro and cyano; Y is Z1R3 or NR7R8 wherein Z1 is O or S; R3 is hydrogen, (C1-C6)alkyl, (C1- C4) alkoxy(C1-C4)alkyl, (C3-C6)cycloalkyl, (C3- C6)cycloalkyl(C1-C4) alkyl, halo(C1-C3) alkyl containing up to three halogens, phenyl or benzyl; and R7 and R8 are, independently, hydrogen, (C1-C4)alkyl, (C1- C4) alkyl substituted with a carboxyl group, or (C1- C4) alkoxy substituted with a carboxyl group or, together, a (C1-C5) alkylene group; Z is O or S; R5 is (C1-C4) alkyl or phenyl(C1-C4)alkyl; and R6 is (C1- C4) alkyl or phenyl (C1-C4) alkyl; and the agronomically acceptable metal and ammonium salts, acid addition salts, and quaternary ammonium addition salts thereof, which possess chemical gametocidal properties and are useful as chemical hybridization agents in plants, particularly cereal grain plants. This class of compounds provides increased male sterilant activity over those 4-oxopyridazines previously known.

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