Imperial Chemical Industries Limited

Zeneca Limited

Imperial Chemical Industries Public Limited Co.

Kevin Beautement

John M Clough

Vivienne M Anthony

Christopher R Godfrey

Paul John deFraine

Patrick J Crowley

Michael J Bushell

Brian K Snell

Ian Ferguson

Stephen P Heaney

Alan J Buckley

Michael G Huchings

Paul J De Fraine

Paul DeFraine

Michael J Bushnell

This invention relates to derivatives of acrylic acid useful as fungicides, to processes for preparing them, to fungicidal compositions containing them, and to methods of combating fungi, especially fungal infections in plants, using them.

Fungicides

Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is a specified linking group; and A, B and E, which may be the same or different, are H, hydroxy, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; except that when Z is unsubstituted phenyl and X and K are oxygen, A, B and E are not all hydrogen.

Fungicidally active compounds of the formula ##STR1## and stereoisomers thereof, wherein A is the group .dbd.CW-- or a nitrogen atom, B is the group .dbd.CX-- or a nitrogen atom, D is the group .dbd.CY-- or a nitrogen atom, and E is the group .dbd.CZ-- or a nitrogen atom, wherein W, X, Y and Z, which may be the same or different, are, for example, hydrogen, halogen, nitro, nitrile, or other defined groups and wherein R.sup.1 and R.sup.2 are alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, cycloalkyl groups, or optionally substituted heteroaromatic, and V is oxygen or sulfur.

Heterocyclic compounds as fungicides

Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2 CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.tbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1 S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.4 CO, CHR.sup.1 NR.sup.4 COR.sup.4, CHR.sup.1 CHR.sup.2 CO, O.N.dbd.CR.sup.1, CHR.sup.1 O.N.dbd.CR.sup.2, CO.OCR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2 CHR.sup.3, OCHR.sup.1 CHR.sup.2, (CH.sub.2).sub.m O, CHR.sup.1 OCHR.sup.2, CHR.sup.1 CHR.sup.2 O, OCHR.sup.1 CHR.sup.2 O, S(O).sub.n CHR.sup.1 CHR.sup.2, CHR.sup.1 S(O).sub.n CHR.sup.2. CHR.sup.1 CHR.sup.2 S(O).sub.n, CR.sup.1 .dbd.NNR.sup.4, NR.sup.4 N.dbd.CR.sup.1, CHR.sup.1 CONR.sup.2, CHR.sup.1 OCO.NR.sup.2, CH.dbd.CHCH.sub.2 O, COCHR.sup.1 CHR.sup.2 O or (R.sup.5).sub.2 P.sup. + CHR.sup.2 Q.sup.- ; A, B and E, which may be the same or different, are H, hydroxy, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, are H, C.sub.1-4 alkyl or phenyl; R.sup.4 is H, C.sub.1-4 alkyl or COR.sup.1 ; R.sup.5 is optionally substituted phenyl;

Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.1, which are the same or different, are, for example, hydrogen, halogen, hydroxy, optionally substituted alkyl, cycloalkyl or aryl among other possible substituents or X and Y when they are in adjacent positions on the ring optionally form a fused ring; and R, R.sup.3 -R.sup.12 are, for example, hydrogen or optionally substituted alkyl among other possible substituents provided R.sup.4 and R.sup.5 are not both hydrogen. The compounds are useful in agriculture, especially as fungicides but also as insecticides and plant growth regulators.

Alphamethoxy acrylic acid derivatives as fungicides

Compounds of formula (I): ##STR1## or a stereoisomer thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sub.2, wherein R.sup.1 and R.sup.2, which are the same of different, are C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 fluoroalkyl containing one, two or three fluorine atoms and Z is either an oxygen or sulphur atom; A is a sulphur atom; X is optionally substituted pyrimidinyl joined to the thienyl ring by a link --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --O--, --S--; and X and Z.sup.1 are selected from the group consisting of hydrogen, halo, C.sub.1 -C.sub.4 alkyl, halo (C.sub.1 -C.sub.4) alkyl, cyano and formyl. The compounds are useful in agriculture, especially as fungicides but also as insecticides and plant growth regulators.

Fungicidally active compounds of the formula ##STR1## and steroisomers thereof, wherein A is the group .dbd.CW--or a nitrogen atom, B is the group .dbd.CX--or a nitrogen atom, D is the group .dbd.CY--or a nitrogen atom, and E is the group .dbd.CZ--or a nitrogen atom, wherein W, X, Y and Z, which may be the same or different, are, for example, hydrogen, halogen, nitro, nitrile, or other defined groups and wherein R.sup.1 and R.sup.2 are alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, cycloalkyl groups, or optionally substituted heteroaromatic, and V is oxygen or sulfur.

Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.1, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted arylalkoxy, optionally substituted aryloxy, optionally substituted heteraryloxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, optionally substituted arylazo, nitro, cyano, --CO.sub.2 R.sup.6, --CONR.sup.7 R.sup.8, --COR.sup.9 --CR.dbd.NR.sup.10, --CR.dbd.NOR.sup.10 or --N.dbd.CR.sup.11 R.sup.12 groups; or the groups X and Y, when they are in adjacent positions on the ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and R, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12, which are the same or different, are hydrogen atoms (provided that R.sup.4 and R.sup.5 are not hydrogen) or optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heterarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl groups; and metal compelxes thereof. The compounds are useful in agriculture, especially as fungicides but also as insecticides and plant growth regulators.

Fungicidal thienyl propenoates

Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.1, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted arylalkoxy, optionally substituted aryloxy, optionally substituted heteraryloxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, optionally substituted arylazo, nitro, cyano, --CO.sub.2 R.sup.6, --CONR.sup.7 R.sup.8, --COR.sup.9 --CR.dbd.NR.sup.10, --CR.dbd.NOR.sup.10 or --N.dbd.CR.sup.11 R.sup.12 groups; or the groups X and Y, when they are in adjacent positions on the ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and R, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, and R.sup.12, which are the same or different, are hydrogen atoms (provided that R.sup.4 and R.sup.5 are not hydrogen) or optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heterarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl groups; and metal complexes thereof. The compounds are useful in agriculture, especially as fungicides but also as insecticides and plant growth regulators.

Thiophene derivatives useful as fungicidal, insecticidal or plant growth

Process for the preparation of a compound of general formula (I): ##STR1## by reacting a compound of general formula (II) ##STR2## (X is halide; rings M and N are optionally substituted) with an optionally substituted phenol in the presence of a base, or with an optionally substituted phenolate salt; preferably in the presence of a catalyst which is a transition metal, a transition metal salt or compound or a mixture thereof.

Process for preparing methyl 3-methoxy-2-(2-phenoxyphenyl)propenoalis

Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.1, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted arylalkoxy, optionally substituted aryloxy, optionally substituted heteraryloxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, optionally substituted arylazo, nitro, cyano, --CO.sub.2 R.sup.6, --CONR.sup.7 R.sup.8, --COR.sup.9 --CR.dbd.NR.sup.10, --CR.dbd.NOR.sup.10 or --N.dbd.CR.sup.11 R.sup.12 groups; or the groups X and Y, when they are in adjacent positions on the ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and R, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 R.sup.9, R.sup.10, R.sup.11 and R.sup.12, which are the same or different, are hydrogen atoms (provided that R.sup.4 and R.sup.5 are not hydrogen) or optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heterarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl groups; and metal complexes thereof. The compounds are useful in agriculture, especially as fungicides but also as insecticides and plant growth regulators.

Growing community of inventors

Wokingham, United Kingdom

Kevin Beautement