Fungicidal 1-benzoxepin derivatives

A compound of general formula (Ia) or (Ib):

• in which:
• Y is selected from the group consisting of a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, the formyl radical, the carboxyl radical, an alkoxy radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, a cycloalkoxy radical, the cycloalkyl part comprising from 3 to 7 carbon atoms, a hydroxyalkyl radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, the nitro radical, an alkylcarbonyl radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, a cycloalkylcarbonyl radical, the cycloalkyl part comprising from 3 to 7 carbon atoms, an alkoxycarbonyl radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, a cycloalkoxycarbonyl radical, the cycloalkyl part comprising from 3 to 7 carbon atoms, a heterocyclyloxycarbonyl radical, an alkylcarbonyloxy radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, a cycloalkylcarbonyloxy radical, the cycloalkyl part comprising from 3 to 7 carbon atoms, an —SR1, —SOR1, —SO2R1, —C(O)NR1R6, —C(O)NR1(OR2), —C(O)NR1(NR2R6), —C(S)NR1R6, —NR1C(O)NR2R6, —NR1C(S)NR2R6, —OC(O)NR1R6, —NR1R6, —NR1(OR2), —C(R1)═NR6, —C(R1)═NR6(OR2), —C(R1)═NR6(NR2R6) or —N═NR1R6 radical, a linear or branched alkyl radical comprising from 1 to 20 carbon atoms, a cycloalkyl radical comprising from 3 to 7 carbon atoms, an aryl, aryloxy, heteroaryl, heteroaryloxy, arylalkyl, arylalkyloxy, heteroarylalkyl, heteroarylalkyloxy, arylcarbonyl, heteroarylcarbonyl, arylcarbonyloxy or heteroarylcarbonyloxy radical, the hydroxyl radical and the cyano radical;
• Z is a divalent radical selected from the group consisting of ═O, ═CR1X, ═CXX′, ═CR1(CN), ═CR1R2, ═CR1(OR2), ═CR1—C(O)R2, ═CR1—C(O)OR2, ═CR1(SR2), ═CR1(NR2R6), ═NR1, ═N(OR1) and ═N(NR1R6);
• X and X′ are identical or different and are selected from the group consisting of fluorine, chlorine, bromine and iodine;
• R1, R2, R3, R3′, R4 and R4′ are identical or different and are selected from the group consisting of hydrogen, a linear or branched alkyl radical comprising from 1 to 20 carbon atoms, a cycloalkyl radical comprising from 3 to 7 carbon atoms, an aryl radical, an arylalkyl radical, a heteroaryl radical and a heteroarylalkyl radical;
• the two substituents R1 and R2 can together form a saturated or unsaturated ring or heterocycle comprising 3 to 8 atoms;
• the two substituents R3 and R4 can together form a saturated or unsaturated ring or heterocycle comprising 3 to 8 atoms,
• R5 is selected from the group consisting of the hydrogen atom, the hydroxyl radical, a linear or branched alkyl radical comprising from 1 to 6 carbon atoms, a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, the formyl radical, the carboxyl radical, an alkoxy radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, a cycloalkoxy radical, the cycloalkyl part comprising from 3 to 7 carbon atoms, the nitro radical, an alkylcarbonyl radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, a cycloalkylcarbonyl radical, the cycloalkyl part comprising from 3 to 7 carbon atoms, an alkoxycarbonyl radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, a cycloalkoxycarbonyl radical, the cycloalkyl part comprising from 3 to 7 carbon atoms, a heterocyclyloxycarbonyl radical, a cycloalkoxycarbonyl radical, the cycloalkyl part comprising from 3 to 7 carbon atoms, an alkylcarbonyloxy radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, a cycloalkylcarbonyloxy radical, the cycloalkyl part comprising from 3 to 7 carbon atoms, an —SR1, —SOR1, —SO2R1, —C(O)NR1R6, —NR1R6, —NR1C(O)NR1R6, —NR1(OR2), —C(R1)═NR6 or —N═NR1R2 radical, a linear or branched alkyl radical comprising from 1 to 6 carbon atoms, a linear or branched alkenyl radical comprising from 1 to 6 carbon atoms, a cycloalkyl radical comprising from 3 to 7 carbon atoms, an aryl, aryloxy, heteroaryl, heteroaryloxy, arylalkyl, arylalkyloxy, heteroarylalkyl, heteroarylalkyloxy, arylcarbonyl, heteroarylcarbonyl, arylcarbonyloxy or heteroarylcarbonyloxy radical, the cyanato radical, the thiocyanato radical, the azido radical and the cyano radical;
• R6 is selected from the group consisting of the hydrogen atom, a linear or branched alkyl radical comprising from 1 to 6 carbon atoms, a phenyl radical, a naphthyl radical, a phenylalkyl radical, the alkyl part being linear or branched and comprising from 1 to 6 carbon atoms, a naphthylalkyl radical, the alkyl part being linear or branched and comprising from 1 to 6 carbon atoms, an alkylcarbonyl radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, an alkoxycarbonyl radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, an N,N′-dialkylaminocarbamoyl radical, the linear or branched alkyl parts comprising from 1 to 6 carbon atoms, an alkylsulfonyl radical, the linear or branched alkyl part comprising from 1 to 6 carbon atoms, an arylsulfonyl radical and an N,N′-dialkylaminosulfonyl radical, the linear or branched alkyl parts comprising from 1 to 6 carbon atoms;
• with the restriction that, for the compound of formula (Ia),
• when Z represents the ═CHCl radical and R1, R2, R3, R4 and R5 each represent a hydrogen atom, then Y cannot represent the methylcarbonyl radical or the methoxycarbonyl radical, the formyl radical, the hydroxymethyl radical, the carboxyl radical, the bromo radical or the cyano radical,
• when Z represents the ═CH2 radical and R1, R2, R3, R4 and R5 each represent a hydrogen atom, then Y cannot represent the methoxycarbonyl or the bromo radical,
• when Z represents the ═O radical and R1, R2, R3, R4 and R5 each represent a hydrogen atom, then Y cannot represent the bromo radical;
• and that, for the compounds of formula (Ib),
• when Z represents the ═CHCl radical and R1, R2, R3, R3′, R4, R4′ and R5 each represent a hydrogen atom, then Y cannot represent the methylcarbonyl radical,
• when Z represents the ═O radical and R2, R3, R3′, R4, R4′ and R5 each represent a hydrogen atom, then Y and R1 cannot represent, both or independently of one another, a hydrogen atom or an alkyl radical comprising 1 to 4 carbon atoms;
• and to their possible geometrical and/or optical isomers, to their possible tautomeric forms and to their salts, N-oxides and metal and semimetal complexes.