N-SUBSTITUTED-3,4,5,6-TETRAHYDROPHTHALAMIDE DERIVATIVE AND HERBICIDE CONTAINING SAID DERIVATIVE AS ACTIVE COMPONENT

• Main Authors: KOBAYASHI TAKANORI, YANAGI MIKIO, YAMADA KURA, NITANI FUMIO
• Format: Patent
• Language: English
• Published: 20.12.1983
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; AGRICULTURE; ANIMAL HUSBANDRY; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; CHEMISTRY; FISHING; FORESTRY; 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

NEW MATERIAL:The compound of formula 1 (R1 is lower alkyl; R2 is H or lower alkyl; R3 is H or 1-8C straight or branched alkyl). EXAMPLE:N-(3-Ethoxycarbonylphenyl)-3,4,5,6-tetrahydrophthalamide. USE:Herbicide having excellent herbicidal effect against the annual weeds such as barnyard grass in paddy rice field and broad-leaved weeds, etc., and also strong herbicidal effect to perennial weeds (e.g. cyperaceous plants). It has low phytotoxicity to rice plant. PROCESS:The compound of formula 1 can be prepared by (a) reacting the 3,4,5,6- tetrahydrophthalic anhydride of formula 2 with m-aminobenzoic acid of formula 3 in a proper solvent at room temperature or under heating, (b) subjecting the resultant compound of formula 4 to dehydrative cyclizaton with a dehydration agent (e.g. DCC) to obtain the compound of formula 5, and (c) reacting the compound with the amine of formula 6 at room temperature-120 deg.C.