Title of Invention

BIPHENYL DERIVATIVES, A COMPOSITION COMPRISING THEM AND ITS APPLICATION AS A FUNGICIDE

Abstract

A fungicidally active compound of formula (I): where Het is a substituted 5- or 6-membered heterocyclic ring; R<sup>1</sup> is hydrogen, formyl, CO-C<sub>1/sub>O-<sub>4/sub>O alkyl, COO-C<sub>1/sub>O-<sub>4/sub>O alkyl, C<sub>1/sub>O-<sub>4/sub>O alkoxy(C<sub>1/sub>O-<sub>4/sub>O)alkylene, CO-C<sub>1/sub>O-<sub>4/sub> alkylenoxy(C<sub>1/sub>-<sub>4/sub>alkyl, propargyl or allenyl; R<sup>2/sup>, R<sup>3/sup>, R<sup>4</sup> and R<sup>5/sup> are each, independently, hydrogen, halogen, methyl or CF<sup>3/sup>; each R<sup>6/sup> is, independently, halogen, methyl or CF3; R<sup>7/sup> is (Z)mC=C(Y<sup>1/sup>), (Z)mC(Y<sup>2sup>)=C(Y<sup></sup>)(Y<sup>3/sup>) or tri(C1-4)2lkylsilyl; X is O or S; Y<sup>1/sup>, Y<sup>2/sup> and Y<sup>3/sup> are each, independently, hydrogen, halogen, C<sub>1/sub>O-<sub>6sub>O alkyl [optionally substituted by one or more substituents each independently selected from halogen, hydroxy, C<sub>1/sub>-<sub>4/sub>1-4 alkoxy, C<sub>1/sub>-<sub>4/sub> haloalkoxy, C<sub>1/sub>-<sub>4/sub> alkylthio, C<sub>1/sub>-<sub>4/sub> haloalkylthio, C<sub>1/sub>-<sub>4/sub> alkylamino, di(C<sub>1/sub>-<sub>4/sub>alkylamino, C<sub>1/sub>-<sub>4/sub> alkoxycarbonyl, C<sub>1/sub>-<sub>4/sub> alkylcarbonyloxy and tri(C<sub>1/sub>-<sub>4/sub> lkylsilyl], C<sub>2sub>-<sub>4/sub> alkenyl [optionally substituted by one or more substituents each independently selected from halogen], C<sub>2/sub>-<sub>4/sub> alkynyl [optionally substituted by one or more substituents each independently selected from halogen], C<sub>3/sub>-<sub>7/sub> cycloalkyl [optionally substituted by one or more substituents each independently selected from halogen, C<sub>1/sub>-<sub>4/sub> alkyl and C<sub>1/sub>-<sub>4/sub> haloalkyl] or tri(C1 4)alkylsilyl; Z is C<sub>1/sub>-<sub>4/sub> alkylene [optionally substituted by one or more substituents each independently selected from hydroxy, cyano, C<sub>1/sub>-<sub>4/sub> alkoxy, halogen, C<sub>1/sub>-<sub>4/sub> haloalkyl, C<sub>1/sub>-<sub>4/sub> haloalkoxy, C<sub>1/sub>-<sub>4/sub> alkylthio, COOH and COO-C<sub>1/sub>-<sub>4/sub> alkyl]; m is 0 or 1; and n is 0, 1 or 2; the invention also relates to novel intermediates used in the preparation of these compounds, to agrochemical compositions which comprise at least one of the novel compounds as active ingredient and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

Full Text

The present invention relates to novel carboxamide derivatives as active ingredients which have microbiocidal activity, in particular fungicidal activity. The invention also relates to preparation of these active ingredients, to novel diphenyl derivatives used as intermediates in the preparation of these active ingredients, to preparation of these novel intermediates, to agrochemical compositions which comprise at least one of the novel active ingredients, to preparation of these compositions and to use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopatliogenic microorganisms, preferably fungi. Fungicidally active carboxamide derivatives are disclosed in JP2001072510. - - JP2001072508,JP2001072507 and JP2001302605. Certain amino- or halo-substituted diphenyl derivatives are disclosed in DE2205732 and JP2001302605. The present invention provides a compound of formula (I): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and suphur, provided that the ring is not 1,2,3-triazole, the ring being substituted by one, two or three groups Ry; R is hydrogen, formyl, CO-C1-4alkyl, COOC1-4alkyl, C1-4alkoxy(C1-4)alkylene, CO-C1-4alkylenoxy(C1-4)alkyl, propargyl or allenyl; R2, R3, R4 and R5 are each, independently., hydrogen, halogen, methyl or CF3; each R6 is, independently, halogen, methyl or CF3; R7 is (Z)mOQY1), (Z)mC(Y])=C(Y2)(Y3) or tri(C1-4)alkylsilyl; each Ry is, independently, halogen, C1-3 alkyl, C1-3haloalkyl, C1-3alkoxy(C1-3)alkylene or cyano; X is 0 or S;Y',Y2andY3 are each, independently, hydrogen, halogen, C1-6 alkyl [optionally substituted by one or more substituents each independently selected from halogen, hydroxy, C1-4alkoxy, C1-4haloalkoxy, C1-4 alkylthio, C1-4haloalkylthio, C1-4alkylamino, di(CM)alkylamino, C1-4alkoxycarbonyl, C1-4alkylcarbonyIoxy and tri(C1-4)alkylsilyl], C2-4 alkenyl [optionally substituted by one or more substituents each independently selected from halogen], C2-4 alkynyl [optionally substituted by one or more substituents each independently selected from halogen], C3.7 cycloalkyl [optionally substituted by one or more substituents each independently selected from halogen, C1-4 alkyl and C1-4haloalkyl] or tri(C1-4)alkylsilyl; Z is C1-4alkylene [optionally substituted by one or more substituents each independently selected from hydroxy, cyano, C1-4alkoxy, halogen, C1-4haloalkyl, C1-4haloalkoxy, C1-4alkylthio, COOH and COO-C1-4alkyl]; m is 0 or 1; and n is 0, 1 or 2. In one particular aspect, the present invention provides a compound of formula (I) as defined above where Y , Y and Y" are each, independently, hydrogen, halogen, C1-4alkyl [optionally substituted by one or more substituents each independently selected from halogen, hydroxy, C1-4alkoxy, C1-4haloalkoxy, C1-4alkylthio, C1-4haloalkylthio, C1-4alkylamino, di(C|.4)alkylamino, C1-4alkoxycarbonyl and tri(CM)a!kylsilyl], C2-4 alkenyl [optionally substituted by one or more substituents each independently selected from halogen], C2-4 alkynyl [optionally substituted by one or more substituents each independently selected from halogen], C3-7 cycloalkyl [optionally substituted by one or more substituents each independently selected from halogen, C1-4alkyl and C1-4haloalkyl] or tri(C1-4)alkylsilyl. In one aspect, the present invention provides a compound of formula (I) as defined above where Z is C1-4alkylene [optionally substituted by one or more substituents each independently selected from hydroxy, cyano, C1-4alkoxy, C1-4haloalkoxy, C1-4 alkylthio, COOH and COO-C1-4alkyl]. In one aspect, the present invention provides a compound of formula (I) as defined above provided that R7 is not C2-6 alkenyl when X is O; R1 is hydrogen; one of R", R , R and R5 is fluorine and the others are all hydrogen; n is 1; and Het is In another aspect, the present invention provides a compound of formula (I) as defined above provided that R7 is not C2-6 alkenyl when X is O; R1, R, R, R4 and R5 are all hvdrosen; and Het is In a further aspect, the present invention provides a compound of formula (I) as defined above provided that R7 is not C2-6 alkenyl when X is 0; R1, R2, R3, R4 and R5 are all hydrogen; n is 1; and Het is In yet another aspect, the present invention provides a compound of formula (I) as defined above provided that R7 is not C2-6 alkenyl in the 4' position when X is O; R1, R3 and R are all hydrogen; R and R are each, independently, hydrogen or fluorine; n is 0; or n is 1; or n is 2 and the two independent R6 substituents are in positions 2',3' or 2',5' or 3',5'; and Het is Halogen is fluorine, chlorine, bromine or iodine [preferably fluorine, chlorine or bromine]. Each alkyl moiety is a straight or branched chain and is, for example, methyl, ethyl, . n-propyl, n-butyl, iso-propyl, n-butyl, sec-butyl, iso-butyl or tert-butyl. Likewise, each alkylene moiety is a straight or branched chain. Haloalkyl moieties are alkyl moieties which are substituted by one or more of the same or different halogen atoms and are, for example, CF3, CF:CK CHF2, CH2F, CC13, CF3CH2, CHF2CH2, CH2FCH2, CH3CHF or CH3CF2. Alkenyl and alkynyl moieties can be in the form of straight or branched chains. The alkenyl moieties, where appropriate, can be of either the (E)- or (Z)-configuration. Examples are vinyl, allyl, ethynyl and propargyl. Cycloalkyl includes cyclopropyl. cyclobutyl, cyclopentyl. cyclohexyl and cycloheptyl. In tri(C1-4)alkylsilyl and in di(C1-4)alkylamino, each alkyl moiety is selected independently. Throughout this description, Me stands for methyl and Et stands for ethyl. It is preferred that Het is pyrazole, pyrrole, thiophene, furan, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine. 5.6-dihydropyran or 5.6-dihydro-1.4-oxathiine [more preferably pyrazole, pyrrole, thiophene, furan, thiazole, oxazole, pyridine, pyrimidine, pyridazine or 5.6-dihydropyran; yet more preferably pyrazole, pyrrole, pyridine or thiazole; and even more preferably pyrazole, pyrrole or thiazole]. In one aspect it is preferred that Het is pyrazole, pyrrole, thiophene, furan, thiazole, isothiazole, oxazole, isoxazole, pyrazine, pyrimidine, pyridazine, 5.6-dihydropyran or 5.6-dihydro-1.4-oxathiine [more preferably pyrazole, pyrrole, thiophene, furan, thiazole, oxazole, pyrimidine, pyridazine or 5.6-dihydropyran and even more preferably pyrazole, pyrrole or thiazole]. Preferably R1 is hydrogen, propargyl, allenyl, formyl, COMe, COEt or COCH2OMe. More preferably R1 is hydrogen. Preferably R is hydrogen. Preferably R3 is hydrogen. Preferably R is hydrogen. Preferably R5 is hydrogen or halogen. More preferably R5 is hydrogen or fluorine. Even more preferably R is hydrogen. In one aspect of the invention R7 is tri(C1-4)alkylsilyl. Preferably Y1, Y2 and Y3are, independently, hydrogen, halogen, C1-6 alkyl, C1-3 haloalkyl, C1-4(haloalkoxy)C1-4alkyl, C1-4(haloalkylthio)C1-4alkyl, trimethylsilyl, C2-1 alkenyl, C2-4 haloalkenyl or C3-6 cycloalkyl (optionally substituted by one or more substituents each independently selected from halogen and C1-2 alkyl). Preferably Z is C1-2 alkylene [which may be optionally substituted by one or more substituents each independently selected from halogen, C1-4haloalkyl and C1-4haloalkoxy]. Preferably R7 is in the 4' position. Preferably R is vinyl [optionally substituted by one to three substituents each independently selected from halogen, C1-4alkyl, C1-3 haloalkyl, C3-6 cycloalkyl (optionally substituted by one to five substituents each independently selected from halogen, CH3 and C1-2 haloalkyl) and trimethylsilyl], ethynyl [optionally substituted by one substituent selected from cyclopropyl, cyclopentyl and cyclohexyl (each optionally substituted by one to five substituents each independently selected from halogen, CH3 and C1-2 haloalkyl), halogen, C1-6 alkyl, C1-4 haloalkyl, C2-4 alkenyl, C2-4 haloalkenyl and tri(Ci^)alkylsilyl], allyl [optionally substituted by one to three substituents each independently selected from halogen, CH3, C1-2 haloalkyl and trimethylsilyl], propargyl [optionally substituted by one to three substituents each independently selected from halogen, C1-4alkyl, C1-2 haloalkyl and trimethylsilyl] or tri(C1-4)alkylsilyl. In one particular aspect R7 is preferably vinyl [optionally substituted by one to three substituents each independently selected from halogen, C1-4alkyl, C1-3 haloalkyl, C3-6 cycloalkyl and trimethylsilyl], ethynyl [optionally substituted by one substituent selected from halogen, C1-4alkyl, C1-4haloalkyl, cyclopropyl (optionally substituted by one to five substituents each independently selected from halogen, CH3, C1-4haloalkyl and trimethylsilyl) and trimethylsilyl], allyl [optionally substituted by one to three substituents each independently selected from halogen, CH3, C1-2 haloalkyl and trimethylsilyl], propargyl [optionally substituted by one to three substituents each independently selected from halogen, CH3, C1-2 haloalkyl and trimethylsilyl] or tri(C1-4)alkylsilyl. In another particular aspect R7 is preferably vinyl [optionally substituted by one to three substituents each independently selected from halogen, C1-4alkyl, C1-4haloalkyl, C3-6 cycloalkyl and trimethylsilyl], ethynyl [optionally substituted by one substituent selected from - • halogen, C1-4alkyl, C1-4haloalkyl and trimethylsilyl], allyl [optionally substituted by one to three substituents each independently selected from halogen, CH3, C1-2 haloalkyl and trimethylsilyl], propargyl [optionally substituted by one to three substituents each independently selected from halogen, CH3, C1-2 haloalkyl andtrimethylsilyl] or tri(C1-4)alkylsilyl. More preferably R7 is CH=CH2, CH=CH(CH3), CH=CHSiMe3, CH=CF2, CH=CC12, C(CH3)=CC12, CH=CBr2, C(CH3)=CBr2, C(CH3)=CF2> CH=CFC1, CH=CFBr, C(CH3)=CFC1, C(CH3)=CFBr, CH=CFMe, CH=CBrMe, CH=CClMe, CH-CHBr, CH=CHF, CH=CHC1, CF=CF2, CC1=CF2, CC1=CH2, CBr=CH2, CF=CH2, C(CF3)=CFBr, C(CF3)=CFC1. C(CF3)=CBr2, C(CF3)=CC12, C(CF3)=CF2, C(CF3)=CH2, CF=CHF, CH=CHCF3, CH=CFCF2C1, CH=CC1CF2C1, CH=CBrCF2Cl, CH=C(CF3)2, CH=CHC2F5, CH=CHCF(CF3)2, C(CH3)=CHCF3, C(CH3)=CFCF3, C(CH3)=CC1CF3, C(CH3)=CBrCF3, CH=CC1CF3, CH=CC1C2F5, CH=CBrCF3, CH=CFC2F5, CH=CFCF3, CH2CH=CH2, CH2CH=GF2, CH2CH=CC12, CH2CH=CBr2, CH2CH=CFBr, CH2CH=CFC1, CH2CH=CC1CF3, CH2CH=CHSiMe3, C=CH, OCSiMe3, OCSiEt3, OCSiMe2C(CH3)3, OCC1, OCBr, OCF, C=CCF3, OCCF2H, C=CCF2C1, OCCF2Me, OCCF2Et. OCCHFC1, OCCF2Br, C=CC2F5, OCCF(CF3)2, C=CCHF(CF3), OCCH2F, OCCH(Me)F, C=CCH(Et)F, C=C1-4e, C=CCH2Me, OCCHMe2, C=CCH2CHMe2, OCC1-4e3, OCCH2C1-4e3, C=CCH2SiMe3, OCC1-4e2Cl, OCC1-4e2F, OCCH2OMe, OCCH2CF3, C=CC1-4e2OMe, OCC1-4e2OH, C=CC1-4e2OCOMe, CsCC(Me)=CH2, C=CCF=CF2, C=C(cyclopropyl), OC(cyclopentyl), OC( 1 -F-cyclopentyl), CH2C=CH, CF2OCH, CHFOCH, CH(CF3)C=CH, SiMe3, CH2OCC1-4e3 or CH2OCSiMe3. In one particular aspect R7 is more preferably CH=CH2, CH=CH(CH3), CH=CHSiMe3, CH=CF2, CH=CC12, C(CH3)=CC12, CH=CBr2, CF=CF2, CC1=CH2, CBr=CH2, CF=CH2, CF-CHF, CH=CHCF3, CH=CG1CF3, CH=CBrCF3, CH2CH=CH2, CH2CH=CHSiMe3, OCH, C=CSiMe3, C=CSiEt3, OCSiMe2C(CH3)3, C=CC1, OCBr, C=CCF3, C=CCF2H, OCCF2Cl, OCCF2Br, OCCF(CF3)2C=C1-4e, OCCHMe2, OCC1-4e3) OCC1-4e2Cl, C=CCH2OMe, C=C(cycloC3H5), OC(cycIoC5H9), CH2OCH, SiMe3 or CH2OCSiMe3. Even more preferably R7 is CH=CF2, CH=CC12, C(CH3)=CC12, CH=CBr2, C(CH3)=CBr2, C(CH3)=CF2, CH=CFC1, CH=CFBr, C(CH3)=CFC1, C(CH3)=CFBr, CH=CHBr, CH=CHF, CH=CHC1, CC1=CH2, CH=CHCF3, CH=CFCF2C1, CH=CC1CF2C1, CH=CBrCF2Cl, CH=C(CF3)2, CH=CHC2F5, CH=CHCF(CF3)2, C(CH3)=CHCF3, CH=CC1CF3, CH=CC1C2F5, CH=CFC2F5, CH=CBrCF3, CH=CFCF3, CH2CH=CC1CF3, CH2CH=CC12, CH2CH=CBr2, OCH, OCSiMe3, OCSiEt3, C=CSiMe2C(CH3)3. C=CC1, C=CCF3, OCCF2H, OCCF2Cl. OCCHFC1, OCCF2Me, C=CCF2Et, OCCHFEt, OCCF2Br, OCCF(CF3)2, OCCF2CF3, C=CCHF(CF3), C=CCH2F, OCCH(Me)F, C=C1-4e. OCCHMe2. C-=CCH2Me, C=CCH2CHMe2, OCC1-4e3, C=CCH2C1-4e3. OCC1-4e2F, C=CCH2CF3, OC(cyclopropyl),C=C(cyclopentyl), OC(l-F-cyclopentyl), OCC(Me)=CH:, OCCF=CF2, C=CCH2SiMe3, CH2OCH, CF2OCH or CHFOCH. In one particular aspect R7 is even more preferably CH=CH2, CH=CHSiMe3, CH=CF2, CH=CC12, CH=CBr2, CF=CF2, CC1=CH2, CBr=CH2, CF=CHF, CH=CHCF3, CH=CC1CF3, OCH, OCSiiMe3, OCC1, OCBr, OCCF3, C=C1-4e, OCC1-4e3, C=CCHMe2, OC(cycloC3H5), CH2OCH, SiMe3 or CH2OCSiMe3. Yet more preferably R7 is CH=CF2, CH=CC12, CH=CBr2, CH=CFC1, CH=CFBr, CH=CHBr, CH=CHF, CH=CHC1, CC1=CH2, CH=CHCF3, CH=CFCF2C1, CH=CC1CF2C1, CH=CBrCF2Cl, CH=C(CF3)2, CH=CHC2F5, CH=CC1CF3, CH=CBrCF3, CH=CFCF3, OCH,. OCSiMe3, OCC1, OCCF3, C=CCF2H, OCCHFC1, OCCHF(CF3), OCCF2Cl, OCCF2Me, C=CCF2Br. OCCFjCF3, OCCH2F, OCCH(Me)F, OC1-4e, C=CCHMe2, OCCH2CHMe2, OCC1-4e3, OCCCH2C1-4e3, C=CC1-4e2F, OCCH2CF3, OC(cyclopropyl), OC(cyclopentyl), OC(l-F-cyclopentyl), CH2OCH, CF2C=CH, CHFOCH or C=CCH2Me. In one particular aspect R7 is yet more preferably CH=CHSiMe3, CH=CF2, CH=CC12, CH=CBr2, CF=CF2, CC1=CH2, CBr=CH2, CF=CHF, CH=CHCF3, CH=CC1CF3, OCH, OCSiMe3, OCC1, OCBr, OCCF3, OC1-4e, OCC1-4e3, OCCHMe2, OC(cycloC3H5), CH2OCH, SiMe3 or CH2OCSiMe3. Preferably nitrogen atoms in the Het ring are, independently, either unsubstituted or substituted by Ry. When Ry is a substituent on a nitrogen atom it is preferably C1-3 alkyl, C1-3 haloalkyl or methoxymethylene; more preferably C1-2 alkyl, CF3, CF2C1, CHF2, CH2F or methoxymethylene; even more preferably methyl, CHF2 or methoxymethylene; yet more preferably methyl Or methoxymethylene; and most preferably methyl. Preferably carbon atoms in the Het ring which are not bonded to the atom substituted by CXNR1 are, independently, either unsubstituted or substituted by Ry. When Ry is a substituent on a carbon atom which is not bonded to the atom substituted by CXNR it is preferably halogen, C1-5 alky], C1-3 haloalkyl or methoxymethylene; more preferably chloro, methoxymethylene, CH3, CHF2 or CF3; yet more preferably chloro, CH3, CHF: or CF3; and even more preferably CH3 or CF3.There may be one or two carbon atoms in the Het ring bonded to the atom substituted by CXNR1; preferably such carbon atoms are, independently, either unsubstituted or substituted by Ry. When Ry is a substituent on a carbon atom bonded to the atom substituted by CXNR1 it is preferably halogen,C1-3alkyl orC1-3haloalkyl; more preferably chloro, fluoro, bromo, C1-2 alkyl, CF3, CF2CI, CHF2, CH2F; and even more preferably chloro, fluoro, bromo, methyl/ CF3,CHF2orCH2F. More preferably, when there is only one carbon,atom in the Het ring bonded to the atom substituted by CXNR1 that carbon atom is substituted by Ry. More preferably, when there are two carbon atoms in the Het ring bonded to the atom substituted by CXNR1 one such carbon atom is substituted by Ry and the other carbon atom is either unsubstituted or is substituted by fluoro, chloro or methyl. Preferably m is 0. Preferably n is 0. Preferably X is O. Compounds of formula (II): where R1, R2, R3, R4, R5, R6, R7 and n are as defined above for a compound of formula (I), are also novel [except for the compound of formula (II) where R1, R2, R3, R4 and R are each hydrogen, n is 0 and R7 is CH=CHCH2C02H] and are useful as intermediates in the preparation of compounds of formula (I). Therefore, in another aspect the present invention provides a compound of formula (II), where R',R2, R,R4, R5. R6, R7 and n are as defined above for a compound of formula (I) provided that when R1, R", R, R4 and R5 are each hydrogen and n is 0 then R7 is not CH=CHCH2C02H. The preferred values for R1, R2, R3, R4, R5, R6, R7 and n for a compound of formula (II) are as defined above for a compound of formula (I). Many compounds of formula (III): where R2, R3, R4, R5, R6, R7 and n are as defined above for a compound of formula (I) and Hal is bromo, chloro or iodo, are also novel and are useful as intermediates in the preparation of compounds of formula (I). Certain compounds of formula (III) are already known; Table 0 shows known compounds of formula (Ilia) where Hal, R2, R3, R4 and R7 are as defined in Table 0. Therefore, in a farther aspect the present invention provides a compound of formula (HI), where R2, R3, R4, R5, R6, R7 and n are as defined above for a compound of formula (I) and Hal is bromo, chloro or iodo; provided that the compound is not a compound of fonnula (EUa) according to Table 0. The preferred values for R2, R3, R4, R5, R6, R7 and n for a compound of formula (HI) are as defined above for a compound of formula (I). Preferably Hal is bromo or chloro. More preferably Hal is bromo. The compounds of formulae (I), (II) and (ID) may exist as different geometric or optical isomers or in different tautomeric forms. For each formula, this invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds, The compounds in Tables 1 to 13 below illustrate compounds of the invention. Table 1 Throughout this description, temperatures arc given in degrees Celsius; "NMR" means nuclear magnetic resonance spectrum; MS stands for mass spectrum; MM or M*+l are signals in the mass spectrum respectively corresponding to the molecular weight minus 1 or the molecular weight plus 1; and "%" is percent by weight, unless corresponding concentrations are indicated in other units* Table 14 shows selected melting point, selected molecular ion and selected NMR data, all with CDCh as the solvent (unless otherwise stated; if a mixture of solvents is present, this is indicated as, for example, (CDCI3 / d$-DMSO)), (no attempt is made to list all characterising data in all cases) for compounds of Tables 1 to 13* Unless otherwise stated, the data relate to a cis/trans mixture of each compound. The compounds according to the present invention may be prepared according to the* following reaction schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I). There are a number of alternative methods for preparing a compound of formula (I). Method A A compound of formula (I) may be prepared by reacting a compound of formula (II) with a compound of formula Het-C(=0)OR' [where R' is C1-4alkyl] in the presence of strong base [for example NaH or sodium hexamethyldisilazane], in a dry polar solvent [preferably THF] and at a temperature between -10°C and the boiling point of the solvent [preferably at ambient temperature]. The article by J.Wang et al, Synlett 2001,1485 provides details of analogous preparations. Method B A compound of formula (I) may be prepared by reacting a compound of formula (II) with a compound of formula Het-COK^R" [where R" is OH or a leaving group, such as CI, Br, F or 0C(=:O)C1-4alkyl] in an inert organic solvent [such as ethylacetate, dichloromethane, dioxane or DMF] and at a temperature between -10°C and the boiling point of the solvent [preferably at ambient temperature]. If R" is OH, the reaction is carried out in the presence of an activating agent [for example BOP-C1] and two equivalents of a base [such as a tertiary [where FG is a functional group which is convertible to R7 in one or more synthetic steps]. Functional group interconversions are standard procedures for a person skilled in the art. There are many methods described in the literature, which can be used as such or with modifications according to the functionalities present; Table A gives literature references (some of which also cite further appropriate references) which are specifically relevant to the preparation of a compound of formula (I) by the interconversion of FG to R7. It is apparent to the person skilled in the art that the literature examples given in Table A are not necessarily limited to the preparation of the specifically mentioned R7 but can be also applied by analogy to the preparation of other structurally related R7 1 week old barley plants cv. Regina are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. Two days after application, the barley plants are inoculated by spraying a spore suspension (3xl04conidia/ml) on the test plants. After an incubation period of 4 days at 20°C and 95%r.h. in a greenhouse the disease incidence is assessed. Infestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08, 1.10, 1.12, 1.13, 1.15, 1.16, 1.18, 1.19, 1.22, 1.24, 1.33, 1.36. 1.35, 1.56, 1.57, 1.60, 1.66, 1.67, 1.69, 1.70, 1.77, 1.78, 1.81, 1.106, 1.107, 1.138, 1.139, 1.151, 1.152, 1.154, 1.155, 1.182, 1.185, 1.251, 1.252.2.01,2.08,2,66,3.01,3.08,3.12,3.18,3.32,3.35, 3.56, 3.66, 3.69, 9.01, 9.06,9.15? 9.21, 9.41,9.50, 9.53, 9.59, 9.62, 15.25, 15.26 and 15.28. Example B-9: Action against Alternaria solani / tomato (Early blight on tomatoes) 4 week old tomato plants cv. Roter Gnom are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. Two days after application, the tomato plants are inoculated by spraying a spore suspension (2xl05conidia/ml) on the test plants. After an incubation period of 3 days at 20°C and 95%r.h. in a growth chamber the disease incidence is assessed. Infestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08, 1.10, 1.13, 1.15, 1.16, 1.19, 1.22, 1.24, 1.33, 1.35, 1.36, 1.56, 1.57, 1.67, 1.69, 1.70, 1.77, 1.78, 1.81, 1.107, 1.151, 1.152, 1.154, 1.155, 1.182, 1.185, 1.251, 1. 252, 2.01, 3.01, 3.08, 3.12, 3.32, 3.35, 3.56, 3.69, 9.01, 9.06,9.15, 9.41, 9.50, 9.62 and 15.26. Example B-l 0: Action against Uncinula necator / grape (Powdery mildew on grapes) 5 week old grape seedlings cv. Gutedel are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application, the grape plants are inoculated by shaking plants infected with grape powdery mildew above the test plants. After an incubation period of 7 days at 26°C and 60%r.h. under a light regime of 14/10hours (light/dark) the disease incidence is assessed. Infestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08, 1.10, 1.12, 1.13, 1.18, 1.19, 1.24, 1.33, 1.56, 1.57, 1.60, 1.66, 1.67, 1.70, 1.77, 1.78, 1.81, 1.106, 1.107, 1.138, 1.139, 1.151, 1.152, 1.154, 1.155, 1.182, 1.185, 1.251, 1. CLAIMS 1. A compound of formula (I) as claimed in claim 1 where Het is pyrazole, pyrrole. thiophene. furan, thiazole. isothiazole, oxazole. isoxazole, pyridine, pyrazine, pyrimidine, pyridazine. 5.6-dihydropyran or 5.6-dihydro-1.4-oxathiine. A compound of formula ' I) as claimed in claim 1 or 2 where R is hydrogen, propargyl, allenyl, formyl, COMe, COEt or COCH2OMe. A compound of formula * I) as claimed in claim L 2 or 3 where Y , Y" and Y" are. independently, hydrogen, halogen. C1-6 alkyl, C1-3 haloalkyl, C1-4(haIoalkoxy)C1-4alkyl, C1-4(haloalkyIthio)C1-4 alkyl, trimethylsilyl. C?-4 alkenyl, C2-4haloalkenyl or C3-8 cycloalkyl (optionally substituted by one or more substituents each independentlY' selected from halogen and C1-2 alkyl). A compound of formula {D as claimed in claim 1. 2, 3 or 4 where m = 0. A compound of formula (h as claimed in claim 1. 2, 3, 4 or 5 where Z is C1-2alkylene [which may be optionally substituted by one or more substituents each independently-selected from halogen,C2-4 haloalkyl and C1-4 haloalkoxy]. A compound of formula (T) as claimed in claim 1. 2, 3, 4 5 or 6 where R is in the 4' position. A compound of formula (I) as claimed in claim 1, 2, 3, 4 5, 6 or 7 where n = 0. A compound of formula (II): where R1, R:, R, R4, R, R6, R' and n are as defined in claim 1; provided that when R'. R2, R-, R4 and R5 are each hydrogen and n is 0 then R7 is not CH=C(H)CH:CO:H. A compound of formula (III): - where R2, R3, R4, R5, R6: R7 and n are as defined in claim 1 and Hal is bromo, chloro or iodo; provided that the compound is not a compound of formula (Ilia) according to Table 0. A composition for controlling microorganisms and preventing attack and infestation of plants therewith, wherein the active ingredient is a compound of formula (I) as claimed in claim 1 together with a suitable carrier. A method of controlling or preventing infestation of cultivated plants by phytopathogenic microorganisms by application of a compound of formula (I) as claimed in claim 1 to plants, to parts thereof or the locus thereof.

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1367-CHENP-2005 CORRESPONDENCE OTHERS.pdf

1367-chenp-2005 abstract duplicate.pdf

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1367-chenp-2005 description (complete) duplicate-1.pdf

1367-chenp-2005 description (complete) duplicate.pdf

1367-chenp-2005-abstract.pdf

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1367-chenp-2005-description(complete).pdf

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