Patent IL-101740-A (IL)
Title: a-PHENYLACRYLIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES, INSECTICIDES, ARACHNICIDES AND NEMATOCIDES
IPC: C07D277/32
Filed: 1992-04-30
Abstract: a-Phenylacrylic acid derivatives of the formula R3n R4Ay R1WCC=CH-R2O where: n is 0, 1, 2, 3 or 4, the radicals R3 being identical or different when n is 2, 3 or 4; y is 0 or 1; R1 is hydrogen; C1-C15-alkyl, C3-C15-alkenyl, C3-C8-alkynyl or C3-C8-cycloalkyl, where these groups may carry from one to five halogen atoms; vinyl or ethynyl when W is a direct bond; R2 is cyano, C2-C4-alkenyl, C2-C4-alkynyl; C3-C6-cycloalkyl, where, in addition to carbon atoms, the ring may contain one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, which in the case of oxygen and/or sulfur must not be adjacent to one another, and where the cyclic structure may additionally carry from one to three halogen or C1-C4-alkyl radicals; C1-C4-alkyl which may be unsubstituted or partially or completely halogenated; C1-C2-alkyl which carries C1-C4-alkoxy, C1-C4-alkylthio or a 3-membered to 6-membered cyclic radical which, in addition to carbon atoms may contain one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, which in the case of oxygen and/or sulfur must not be adjacent to one another, and where the cyclic structure may additionally carry from one to three halogen and C1-C4-alkyl radicals; R3 is hydrogen, nitro, cyano, halogen; C1-C4-alkyl, C1-C4-alkoxy, partially or completely halogenated C1-C4-alkyl, partially or completely halogenated C1-C4 alkoxy or C1-C4-alkylthio, or, where n is 2, 3 or 4, two adjacent substituents R3 together form a 1, 3-butadien-1, 4-diyl group which may carry from one to four halogen atoms and/or one or two of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, partially or completely halogenated C1-C4-alkyl, partially or completely halogenated C1-C4-alkoxy or C1-C4-alkylthio; R4 is hydrogen; CHO; alkyl, alkenyl or alkynyl, each of which is unsubstituted or substituted; an unsubstituted or substituted saturated or mono-or diunsaturated cyclic structure which, in addition to carbon atoms, may contain from one to three heteroatoms from the group consisting of oxygen, sulfur and nitrogen as ring members; R:3P-, R:2P(=O) = and R"2P (=O)-, where R: is phenyl and R) is C1-C4-alkoxy; or an unsubstitued or substituted mononuclear to trinuclear aromatic system which, in addition to carbon atoms, may contain from one to four nitrogen atoms or from one to three heteroatoms selected from the group consisting of two nitrogen atoms and one oxygen or sulfur atom; W is a direct bond, oxygen, sulfur or nitrogen, where the nitrogen may carry hydrogen, C1-C4-alkyl or C1-C4-alkoxy; A is -O-; -C(=O)-; -O-C(=O)-; -C(=O)-O-; -S-; -S(=O)-; -O-S(=O)-; -S(=O)-O-; -S(=O)2-; -O-S(=O)2-; -S(=O)2-O-; -NR5-; -O-NR5-; -NR5-C(=O)-; -C(=O)-NR5-; -NR5-C(=O)-NR6-; -S(=O)-NR5-; -NR5-S(=O)2-; -S(=O)2-NR5-; -N=N-; -NR5-NR6-; -NR5-NR6-C(=O)-; -C(=O)- NR5-NR6-; -NR5-NR6-S(=O)2-; -S(=O)2-NR5-NR6-; -O-(C2-C4-alkylene)-O-; -C(=O)-(C2-C4-alkylene)-O-; -O-C (=O) - (C2-C4-alkylene) -O-; -C (=O) -O- (C2-C4 -alkylene) -O-; -S- (C2-C4-alkylene) - O-; -S (=O)2- (C2-C4-alkylene)-O-; -O-S (=O)2- (C2-C4- alkylene) -O-; -S(=O)2-O- (C2-C4-alkylene) -O-; -NR5- (C2-C4-alkylene)-O-; -O-NR5- (C2-C4-alkylene)-O-; -NR5-C (=O) - (C2-C4-alkylene)-O-; -C (=O) -NR5- (C2-C4-alkylene) -O-; -NR5-C (=O) -NR6- (C2-C4-alkylene) -O-; -NR5-NR6- (C2-C4-alkylene) -O-; -NR5-NR6-C (=O) - (C2-C4-alkylene) -O-; -C (=O) - NR5-NR6 - (C2-C4 - alkylene) -O-; C1-C6-alkylene, C2-C6-alkenylene or C2-C6-alkynylene, where these carbon chains may carry from one to four radicals selected from the group consisting of C1-C4 alkyl and halogen, and may be interrupted by one of the following groups or bonded to R4 or to the phenyl ring by one of the following groups; -O-, -S-, -NR5-, -C(=O)-, -C(=O) -O-, -O-C (=O)-, -S(=O)-, -S(=O)2-, -S(=O)2-O-, -O-S(=O)2-, -NR5-C (=O)-, -C (=O) -NR5-, NR5-C(=O) -NR6-, -N=N-, -NR5-NR6-, -NR5-NR6-C (=O) - and -C (=O) -NR5-NR6-; R5 and R6 independently of each other are hydrogen, C1-C4-alkyl or C1-C4-alkoxy; with the provision that: (1) when n is 0, R1 is C1-C5-alkyl, W is oxygen and R4 is unsubstituted or substituted phenyl, then -Ay- is not one of the following chains: -O-, -CH2O-, C-, :-OCH2-, -CH2CH2-, -CH=CH-, -C -oxy-C2-C12- alkyleneoxy, -thio-C2-C12 - alkyleneoxy or -methylenoxy-C2-C12- alkyleneoxy; and (2) when n is 0, R1 is C1-C5-alkyl and W is oxygen, then -Ay- is not one of the following chains: -C(=O)-O-CH2-, -C1-C6-alkylene-C(=O)- O-CH2-, or C2-C6- alkenylene-C(=O)-O- CH2-, where the alkylene and the alkenylene groups may carry halogen atoms or hydroxyl groups.