Zeneca Limited

Imperial Chemical Industries Limited

Ian R Matthews

John M Clough

Christopher R Godfrey

Paul A Worthington

Patrick J Crowley

Paul J De Fraine

Don R Baker

John M Cox

Paul John deFraine

Karl J Fisher

Stephen Christopher Smith

Christopher Richard Ayles Godfrey

David Bartholomew

Russell Martin Ellis

Shaheen Khatoon Vohra

Brian L Pilkington

Neal R Bird

Christoher R Godfrey

Kevin James Gillen

John Williams

David Seaman

Carbonate, carbamate, thiocarbonate dithiocarbonate and thiocarbomate derivatives useful as fungicides

Compounds of formula (XXIII): ##STR1## wherein p is 0 or 1, and processes for making such compounds.

O-methyloximes of benzopyran-3,4- and benzofuran-2,3-diones and methods

Compounds, useful as plant fungicides, having the formula (I): ##STR1## or a stereoisomer thereof, wherein A is CH or N, B is OCH.sub.3 or NHCH.sub.3, X is CH.sub.2, CH.sub.2 O, O or S, Y is R.sup.1 --C.dbd.C--R.sup.2 or R.sup.1 --CH--CH--R.sup.2 wherein R.sup.1 and R.sup.2 are independently H, halo, hydroxy, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano, nitro, amino, mono- or dialkylamino, alkanoylamino, carboxy, alkoxycarbonyl, aminocarbonyl, mono- or di-alkylaminocarbonyl, alkylcarbonyloxy, optionally substituted aryl, optionally substituted aralkyl or optionally substituted aryloxy or R.sup.1 and R.sup.2 join to form with the carbon atoms to which they are attached an optionally substituted benzene ring, and Z is CH.sub.2, CHCH.sub.3, C(CH.sub.3).sub.2 or C.dbd.O.

Fungicidal acrylate derivatives

Described herein are compounds of Formula (XX) and Formula (XXIV), shown below, and processes of making same. ##STR1## wherein p is 0 ##STR2## wherein p is 1, and Y is chlorine or bromine.

Intermediates for the preparation of fungicides

A process for the preparation of a compound of general formula II: ##STR1## wherein R.sup.1 is hydrogen, or C.sub.1 -C.sub.10 hydrocarbyl or heterocyclyl having 3 to 8 ring atoms, either of which may optionally be substituted; each R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is independently hydrogen or C.sub.1 -C.sub.4 alkyl; A is an optionally substituted aromatic or heteroaromatic ring system; and R.sup.21 is hydrogen, halogen, OH or OCONHR.sup.1, wherein R.sup.1 is as defined above; the process comprising cyclizing a compound of general formula III: ##STR2## wherein A, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.21 are as defined in general formula II and R.sup.25 is a leaving group such as a halogen atom; under basic conditions.

Process for preparing pyrrolidinones

A compound of the formula: ##STR1## useful as an intermediate in the preparation of fungicides.

Fungicides

Fungicidal and insecticidal compounds having the general formula (I): ##STR1## or a stereoisomer thereof, wherein A is CH or N; B is OCH.sub.3 or NHCH.sub.3 ; one of L and M is N and the other is S or O; X is an optionally substituted carbocyclic or heterocyclic group; and n is 0 or 1.

Oxa- and thiadiazole derivatives

Fungicidal compounds having the formula (I): ##STR1## and stereoisomers thereof, wherein A is hydrogen, halo, hydroxy, 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 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted heterocyclyloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted aryloxy, optionally substituted heterocyclyloxy, nitro halo cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein is 0, 1 or 2, (CH.sub.2).sub.m PO(OR.sup.3).sub.2 wherein m is 0 or 1, or R.sup.1 and R.sup.2 join to form a carbocyclic or heterocyclic ring system; R.sup.3 and R.sup.4, which are the same or different, are hydrogen, optionally substituted alkyl, optionally substituted aralkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl, or R.sup.3 and R.sup.4 join to form an optionally substituted heterocyclic ring; and R.sup.5 and R.sup.6 are independently hydrogen or C.sub.1-4 alkyl.

Fungicides dizinyl oxime ethers

Fungicidal compounds having the formula (I): ##STR1## and stereoisomers thereof, wherein A is hydrogen, halo, hydroxy, 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 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted heterocyclyloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted aryloxy, optionally substituted heterocyclyloxy, nitro, halo, cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein n is 0, 1 or 2, (CH.sub.2).sub.m PO(OR.sup.3).sub.2 wherein m is 0 or 1, or R.sup.1 and R.sup.2 join to form a carbocyclic or heterocyclic ring system; R.sup.3 and R.sup.4, which are the same or different, are hydrogen, optionally substituted alkyl, optionally substituted aralkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl, or R.sup.3 and R.sup.4 join to form an optionally substituted heterocyclic ring; and R.sup.5 and R.sup.6 are independently hydrogen or C.sub.1-4 alkyl.

Fungicides aromatic oxime amides

Compounds having the general formula (I): ##STR1## and optical isomers thereof, wherein X is oxygen or sulphur; R.sup.1 is halogen, C.sub.1-4 alkoxy or C.sub.1-4 haloalkoxy; R.sup.2 and R.sup.3, which are the same or different, are hydrogen, --CO.sub.2 R.sup.5 or C.sub.1-4 alkyl; R.sup.4 is hydrogen, cyano, C.sub.1-4 alkyl (optionally substituted with cyano or halogen), --(CH.sub.2).sub.n CO.sub.2 R.sup.6, --CONR.sup.6 R.sup.7, C.sub.3-6 cycloalkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, optionally substituted phenyl or optionally substituted heteroaromatic; or the group CR.sup.2 R.sup.3 R.sup.4 can form an allene moiety optionally substituted with C.sub.1-4 alkyl; R.sup.5, R.sup.6 and R.sup.7, which are the same or different, are hydrogen or C.sub.1-4 alkyl; n is 0, 1, 2, 3 or 4; and metal complexes thereof are active as fungicides.

Fungicidal compounds

Compounds of having the general formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is hydrogen, halogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, COR or cyano; R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen, halogen or methyl, provided that R.sup.2, R.sup.3 and R.sup.4 are not all hydrogen and provided that when one of them is methyl then at least one of the other two is not hydrogen; ##STR2## wherein R.sup.5 is hydrogen, C.sub.1-4 alkyl (optionally substituted by hydrogen or cyano), optionally substituted benzyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, cyano, COR, C.sub.1-4 thioalkoxy, C.sub.1-4 thiohaloalkoxy or SNR.sup.7 R.sup.8 ; R.sup.7 and R.sup.8 are independently C.sub.1-4 alkyl or CO.sub.2 R; Y is oxygen or sulphur; R.sup.6 is C.sub.1-4 alkoxy, C.sub.1-4 thioalkoxy or --NR.sup.9 R.sup.10 ; and R.sup.9 and R.sup.10 are independently hydrogen, C.sub.1-4 alkyl, aryl or aralkyl or R.sup.9 and R.sup.10 join to form an optionally substituted heterocyclic ring and R is C.sub.1-4 alkyl or C.sub.3-7 cycloalkyl . These compounds are fungicidally active.

Fungicides which are N-pyridyl-cyclopropane carboxamides or derivatives

A metal complex having the general formula (I): ##STR1## wherein R.sup.1 is C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, or C.sub.2-4 alkenyloxy; R.sup.2 is hydrogen or cyano; R.sup.3 is hydrogen or methyl; X is oxygen or sulphur; M.sub.p Y.sub.q is a transition metal salt wherein M is a transition metal cation, Y is an anion and p and q are independently 1, 2 or 3 according to valency requirements; and n is 1 or 2. The metal complexes of formula (I) are active as fungicides.

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Wokingham, United Kingdom

Ian R Matthews