Imperial Chemical Industries Limited

Zeneca Limited

Other

Syngenta Corporation

Imperial Chemical Industries Public Limited Co.

Vivienne M Anthony

John M Clough

Christopher R Godfrey

Paul John deFraine

Kevin Beautement

Paul J De Fraine

Patrick J Crowley

Michael G Hutchings

Paul A Worthington

Brian K Snell

Ian Ferguson

Michael J Bushell

Kenneth Anderton

David J Tapolczay

Stephen P Heaney

Alan J Buckley

Thomas E Wiggins

Michael G Huchings

Paul DeFraine

Michael J Bushnell

Thomas E Wiggens

Christopher R A Godfrey

Alison Elliott

Christopher A Godfrey

Hetero-aryl compounds having herbicidal, fungicidal and insecticidal activity

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

This invention relates to derivatives of acrylic acid useful in agriculture (especially as fungicides but also as plant growth regulators, insecticides and nematocides), to processes for preparing them, to agricultural (especially fungicidal) compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants, to regulate plant growth and to kill or control insect or nematode pests. The invention provides a compound having the formula (I): ##STR1## and stereoisomers thereof, wherein W is a substituted pyridinyl or substituted pyrimidinyl group linked to A by any of its ring carbon atoms; A is either an oxygen atom or S(O).sub.n wherein n is 0, 1 or 2; X, Y and Z, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl (including haloalkyl), optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, (including haloalkoxy), optionally substituted alkylthio, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.4 N.sup.5, --COR.sup.6 or --S--(O).sub.m R.sup.7 (wherein m is 0, 1 or 2) groups, or any two of the groups X, Y and Z, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R.sup.1 and R.sup.2, which are the same or different, are optionally substituted alkyl (including fluoroalkyl) groups.

Certain pyrimidinyloxy-phenyl acrylates, derivatives thereof and their

This invention relates to derivatives of acrylic acid useful in agriculture (especially as fungicides but also as plant growth regulators, insecticides and nematocides), to processes for preparing them, to agricultural (especially fungicidal compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants, to regulate plant growth and to kill or control insect or nematode pests. The invention provides a compound having the formula (I): ##STR1## and stereoisomers thereof, wherein W is a substituted pyridinyl or substituted pyrimidinyl group linked to A by any of its ring carbon atoms; A is either an oxygen atom or S(O).sub.n wherein n is 0, 1 or 2; X, Y and Z, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl (including haloalkyl), optionally substituted alkenyl, optionally substituted alkynyI, optionally substituted alkoxy, (including haloalkoxy), optionally substituted alkylthio, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, --COR.sup.6 or --S (O).sub.m R.sup.7 (wherein m is 0, 1 or 2) groups, or any two of the groups X, Y and Z, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R.sup.1 and R.sup.2, which are the same or different, are optionally substituted alkyl (including fluoroalkyl) and the like.

Certain fungicides, pesticides and plant growth regulants

This invention relates to derivatives of acrylic acid useful in agriculture (especially as fungicides but also as plant growth regulators, insecticides and nematocides), to processes for preparing them, to agricultural (especially fungicidal) compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants, to regulate plant growth and to kill or control insect or nematode pests. The invention provides a compound having the formula (I): ##STR1## and stereoisomers thereof, wherein W is a substituted pyridinyl or substituted pyrimidinyl group linked to A by any of its ring carbon atoms; A is either an oxygen atom or S(O).sub.n wherein n is 0, 1 or 2; X, Y and Z, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl (including haloalkyl), optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy.

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.

Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is optionally substituted aryl or optionally substituted heteroaryl; Y is oxygen, sulphur or NR.sup.4 ; R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, are hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkenyl; X is halogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkoxy, nitro or cyano; and n is 0 or an integer of 1 to 4; provided that when Y is oxygen, n is 0 and R.sup.1 is unsubstituted phenyl at least one of R.sup.2 and R.sup.3 is other than hydrogen or methyl.

Certain acrylates having fungicidal activity

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

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.

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.

Compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein X is halogen, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, alkenyl, alkynyl, aryl, amino, arylazo, heteroarylalkyl, heteroaryloxyalkyl, acylamino nitro, nitrile, trifluoromethyl, --OR.sup.1, SR.sup.1, --CO.sub.2 R.sup.2, --CONR.sup.3 R.sup.4, --COR.sup.5, --CR.sup.6 .dbd.NR.sup.7, --N.dbd.CR8R.sup.9, --SOR.sup.10 or --SO.sub.2 R.sup.11 ; W, Y and Z, which may be the same or different, are any of the atoms or groups listed for X above and, in addition, may be hydrogen atoms; or any two of the groups W, X, Y and Z, in adjacent positions on the phenyl ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R.sup.1 is alkyl, or cycloalkyl optionally containing a heteroatom in the cycloalkyl ring, alkenyl, acyl, aryl, heteroaryl, aralkyl or heteroarylalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.8, R.sup.9, R.sup.10 and R.sup.11, which may be the same or different, are hydrogen or alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, aralkyl, aryl or heteroaryl; and R.sup.7 is aryl, the alkyl, cycloalkyl, aralkyl, aryloxyalkyl, alkenyl, alkynyl, aryl, amino, arylazo, heteroarylalkyl, heteroaryloxyalkyl, acylamino, acyl, and heteroaryl being optionally substituted. The compounds are useful as fungicides and as plant growth regulators.

Growing community of inventors

Maidenhead, United Kingdom

Vivienne M Anthony