US 4,826,531 AGranted

Pyridine derivatives and their uses as fungicides and insecticides

AssigneeImperial Chemical Industries PLC

InventorsVivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton

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Abstract

Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur; A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups; any two of the groups A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.

Claims12

Dependent claims

A compound having the general formula (1):

##STR24## and stereoisomers thereof, wherein W, which is attached to the pyridine ring at the 2-, 3- or 4-position, is ##STR25## wherein R.sup.1 and R.sup.2, which are the same or different, are C.sub.1-6 alkyl or fluoro(C.sub.1-6)alkyl groups, and Z is either an oxygen or sulphur atom;
A, B, D and E, which are the same or different, are hydrogen or halogen atoms, or hydroxy, C.sub.1-6 alkyl optionally substituted with halogen, hydroxy, alkoxy or phenoxy, (C.sub.1-6)alkoxy, phenyl(C.sub.1-6)alkyl, phenyl(C.sub.1-6)alkoxy, C.sub.2-6 alkenyl optionally substituted with phenyl, C.sub.3-6 alkynyl, phenyl, phenoxy, phenylthio, --NR.sup.1 R", --NHCOR.sup.1, --OCOR.sup.1 (in which R.sup.1 and R.sup.11 are as defined below), phenylazo, nitro cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 NR.sup.4, N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups, n is 0, 1 or 2;
and R.sup.3 and R.sup.4, which are the same or different, are hydrogen atoms or (C.sub.1-6)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl (C.sub.1-4)alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl phenyl or phenyl (C.sub.1-6)alkyl groups;
any foregoing aryl moiety being optionally substituted with one or more of halogen, hydroxy, C.sub.1-4 alkyl, (C.sub.1-4)alkoxy, halo-(C.sub.1-4)alkyl, halo (C.sub.1-4)alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkoxy(C.sub.1-4)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-(C.sub.1-4)alkyl, phenyl, phenoxy, phenyl (C.sub.1-4)alkyl, phenyl (C.sub.1-4)alkoxy, phenyl(C.sub.1-4)akyl, acetyloxy, benzoyloxy, cyano, thiocyanato, nitro, --NR'R", --NHCOR', --NHCONR'R", --CONR'R", --COOR', --OSO.sub.2 R', --SO.sub.2 R', --COR', --CR'.dbd.NR" or --N.dbd.CR'R" in which R' and R" are independently hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl (C.sub.1-4)-alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and metal complexes thereof;
except that when A, B, D and E are all hydrogen, W is attached to the pyridine ring at the 2-position and Z is oxygen, R.sup.1 and R.sup.2 are not both ethyl.

2 more elements

A fungicidal composition comprising, as an active ingredient, an effective amount of a compound of the formula (I):

##STR27## and stereoisomers thereof, wherein W, which is attached to the pyridine ring at the 2-, 3- or 4-position, is ##STR28## wherein R.sup.1 and R.sup.2, which are the same or different, are C.sub.1-6 alkyl or fluoro(C.sub.1-6)alkyl groups, and Z is either an oxygen or sulphur atoms;
A, B, D and E, which are the same or different, are hydrogen or halogen atoms, or hydroxy, C.sub.1-6 alkyl optionally substituted with halogen, hydroxy, alkoxy or phenoxy, (C.sub.1-6)alkoxy, phenyl(C.sub.1-6)alkyl, phenyl(C.sub.1-6)alkoxy, C.sub.2-6 alkenyl optionally substituted with phenyl, C.sub.3-6 alkynyl, phenyl, phenoxy, phenylthio, --NR.sup.1 R", --NHCOR.sup.1, --OCOR.sup.1 (in which R.sup.1 and R.sup.11 are as defined below), phenylazo, nitro cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 NR.sup.4, N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups, n is 0, 1 or 2;
and R.sup.3 and R.sup.4, which are the same or different, are hydrogen atoms or (C.sub.1-6)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl (C.sub.1-4)alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, phenyl or phenyl (C.sub.1-6)alkyl groups;
any foregoing aryl moiety being optionally substituted with one or more of halogen, hydroxy, C.sub.1-4 alkyl, (C.sub.1-4)alkoxy, halo-(C.sub.1-4)alkyl, halo (C.sub.1-4)alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkoxy(C.sub.1-4)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-(C.sub.1-4)alkyl, phenyl, phenoxy, phenyl (C.sub.1-4)alkyl, phenyl (C.sub.1-4)alkoxy, phenyl(C.sub.1-4)alkyl, acetyloxy, benzoyloxy, cyano, thiocyanato, nitro, --NR'R", --NHCOR', --NHCONR'R", -- CONR'R", --COOR', --OSO.sub.2 R', --SO.sub.2 R', --COR', --CR'.dbd.NR" or --N.dbd.CR'R" in which R' and R" are independently hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl (C.sub.1-4)-alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and metal complexes thereof and a carrier or diluent therefor.

1 more element

An insecticidal/nematochidal composition comprising, as an active ingredient, an effective amount of a compound of the formula (I):

##STR29## and stereoisomers thereof, wherein W, which is attached to the pyridine ring at the 2-, 3- or 4-position, is ##STR30## wherein R.sup.1 and R.sup.2, which are the same or different, are C.sub.1-6 alkyl or fluoro(C.sub.1-6)alkyl groups, and Z is either an oxygen or sulphur atom;
A, B, D and E, which are the same or different, are hydrogen or halogen atoms, or hydroxy, C.sub.1 6 alkyl optionally substituted with halogen, hydroxy, alkoxy or phenoxy, (C.sub.1-6)alkoxy, phenyl(C.sub.1-6)alkyl, phenyl(C.sub.1-6)alkoxy, C.sub.2-6 alkenyl optionally substituted with phenyl, C.sub.3-6 alkynyl, phenyl, phenoxy, phenylthio, --NR.sup.1 R", --NHCOR.sup.1, --OCOR.sup.1 (in which R.sup.1 and R.sup.11 are as defined below), phenylazo, nitro cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 NR.sup.4, N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups, n is 0, 1 or 2;
and R.sup.3 and R.sup.4, which are the same or different, are hydrogen atoms or (C.sub.1-6)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl (C.sub.1-4)alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, phenyl or phenyl (C.sub.1-6)alkyl groups;
any foregoing aryl moiety being optionally substituted with one or more of halogen, hydroxy, C.sub.1-4 alkyl, (C.sub.1-4)alkoxy, halo-(C.sub.1-4)alkyl, halo (C.sub.1-4)alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkoxy(C.sub.1-4)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-(C.sub.1-4)alkyl, phenyl, phenoxy, phenyl (C.sub.1-4)alkyl, phenyl (C.sub.1-4)alkoxy, phenyl(C.sub.1-4)alkyl, acetyloxy, benzoyloxy, cyano, thiocyanato, nitro, --NR'R", --NHCOR', --NHCONR'R", --CONR'R", --COOR', --OSO.sub.2 R', --SO.sub.2 R', --COR', --CR'.dbd.NR" or N.dbd.CR'R" in which R' and R" are independently hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl (C.sub.1-4)-alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and metal complexes thereof, and a carrier or diluent therefor.

1 more element

A plant growth regulator composition comprising, as an active ingredient, an effective amount of a compound of the formula (I):

##STR31## and stereoisomers thereof, wherein W, which is attached to the pyridine ring at the 2-, 3- or 4-position, is ##STR32## wherein R.sup.1 and R.sup.2, which are the same or different, are C.sub.1-6 alkyl or fluoro(C.sub.1-6)alkyl groups, and Z is either an oxygen or sulphur atom;
A, B, D and E, which are the same or different, are hydrogen or halogen atoms, or hydroxy, C.sub.1-6 alkyl optionally substituted with halogen, hydroxy, alkoxy or phenoxy, (C.sub.1-6)alkoxy, phenyl(C.sub.1-6)alkyl, phenyl(C.sub.1-6)alkoxy, C.sub.2-6 alkenyl optionally substituted with phenyl, C.sub.3-6 alkynyl, phenyl, phenoxy, phenylthio, --NR.sup.1 R" --NHCOR.sup.1, --OCOR.sup.1 (in which R.sup.1 and R.sup.11 are as defined below), phenylazo, nitro cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 NR.sup.4, N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups, n is 0, 1 or 2;
and R.sup.3 and R.sup.4, which are the same or different, are hydrogen atoms or (C.sub.1-6)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl(C.sub.1-4)alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, phenyl or phenyl (C.sub.1-6)alkyl groups;
any foregoing aryl moiety being optionally substituted with one or more of halogen, hydroxy, C.sub.1-4 alkyl, (C.sub.1-4)alkoxy, halo-(C.sub.1-4)alkyl, halo(.sub.1-4)alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkoxy(C.sub.1-4)alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl(C.sub.1-4)alkyl, phenyl, phenoxy, phenyl (C.sub.1-4)alkyl, phenyl (C.sub.1-4)alkoxy, phenyl(C.sub.1-4 alkyl, acetyloxy, benzoyloxy, cyano, thiocyanato, nitro, --NR'R", --NHCOR', --NHCONR'R", --CONR'R", --COOR', --OSO.sub.2 R', --SO.sub.2 R', --COR', --CR'.dbd.NR" or --N.dbd.CR'R" in which R' and R" are independently hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl (C.sub.1-4)-alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and metal complexes thereof, and a carrier or diluent therefor.

1 more element

Dependencies are inferred from the claim text.