• 专利附录
  • 专利说明
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    • 专利摘要:
    The present invention relates to fungicidal N-[(trisubstitutedsilyl)methyl]carboxamide or its thiocarboxamide derivative, their process of preparation and intermediate compounds for their preparation, their use as fungicides, particularly in the form of fungicidal compositions and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions.
    公开号:AU2011260331A1
    申请号:U2011260331
    申请日:2011-06-01
    公开日:2012-11-08
    发明作者:Jurgen Benting；Peter Dahmen；Philippe Desbordes；Stephanie Gary；Marie-Claire Grosjean-Cournoyer；Hiroyuki Hadano；Ruth Meissner；Rachel Rama；Philippe Rinolfi；Ulrike Wachendorff-Neumann
    申请人:Bayer CropScience AG；
    IPC主号:C07F7-08
    专利说明:
    WO 2011/151368 PCT/EP2011/059024 FUNGICIDE N -[(TRISUBSTITUTEDSILYL)METHYL] -CARBOXAMIDE DERIVATIVES DESCRIPTION The present invention relates to fungicidal N-[(trisubstitutedsilyl)methyl]carboxamide or its 5 thiocarboxamide derivative, their process of preparation and intermediate compounds for their preparation, their use as fungicides, particularly in the form of fungicidal compositions and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions. In publication Gaodeng Xuexiao Huaxue Xuebao (1990), 11(10), 1072-5 [Chemical Abstracts 10 AN115:49790], certain fungicidal N-[(dimethylphenylsilyl)methyl]-2-fu rylcarboxamide derivatives are generically embraced in the following formula: 0 N Si 0 R wherein R can represent various substituents among which an alkyl group or a cyclohexyl group. However, this document does not disclose compounds wherein the 2-furyl ring or the phenyl ring can be 15 substituted or replaced. Furthermore, there is no disclosure in this document of any compound including a cyclopropyl group or a hydrogen atom linked to the nitrogen atom of the carboxamide residue. In international patent application WO-2007/1039615 certain fungicidal N-[(trialkylsilyl)alkyl] carboxamide derivatives are generically embraced in a broad disclosure of numerous compounds of the following 20 formula: o 2 R 3
    R
    4 R2 R W-R Het N n R, R wherein Het can represent a 5-membered heterocyclic ring, n can be 2 to 4, R 1 can represent a hydrogen atom, a Cl-C 6 -alkyl group or a C 3
    -C
    7 -cycloalkyl group, W can represent a silicium atom, X and R 3 can represent a hydrogen atom or a Cl-C 6 -alkyl group, R 2, R 4, R and R6 can represent various substituents 25 among which a Cl-C 6 -alkyl group. However, this document does not disclose compounds wherein n can be 0. Furthermore, there is no disclosure in this document of any compound wherein one of the three substituent R 4, R or R6 can be a (hetero)aromatic ring. In international patent application WO-2008/081011 certain fungicidal N-[(dialkyl-2-pyridylsilyl)methyl] 30 carboxamide derivatives are generically embraced in a broad disclosure of numerous compounds of the following formula: (X) R R20 1- x ' N A N Het 13
    R
    WO 2011/151368 2 PCT/EP2011/059024 wherein Het can represent a 5-membered heterocyclic ring, A can represent a SiR 4
    R
    5 group, R3 can represent a hydrogen atom, a C-C 6 -alkyl group or a C 3
    -C
    7 -cycloalkyl group, R 1 and R 2 can represent various substituents among which a hydrogen atom or a C-C 6 -alkyl group, and R 4 and R 5 can represent a C-C 6 -alkyl group. However, this document does not disclose compounds wherein the 2-pyridine moeity 5 can be replaced by a phenyl group. Furthermore, there is no explicit disclosure in this document of any compound wherein A can be a dialkylsilyl group. In international patent application WO-2010/012795 certain fungicidal N-[(dialkyl-2-phenylsilyl)ethyl] carboxamide derivatives are generically embraced in a broad disclosure of numerous compounds of the 10 following formula: (X), 3 4 Z Z Z I N A Z Z T wherein A can represent a 5-membered heterocyclic ring, T can represent an oxygen atom or a sulfur atom, W can represent a SiZZ 2 group, Z7 can represent a C 3
    -C
    7 -cycloalkyl group, Z' and Z2 can represent a C-C 8 -alkyl group, and Z3, Z4, Z5 and Z6 can represent various substituents among which a 15 hydrogen atom or a C-C 8 -alkyl group. However, this document does not disclose compounds wherein the SiZZ 2 group can be linked to the (thio)carboxamide moiety by a unique methylene group or wherein Z7 can represent a hydrogen atom or a C-C 6 -alkyl group. Furthermore, there is no explicit disclosure in this document of any compound wherein W can be a dialkylsilyl group. 20 It is always of high-interest in the field of agrochemicals to use pesticidal compounds more active than the compounds already known by the man ordinary skilled in the art whereby reduced amounts of compound can be used whilst retaining equivalent efficacy. Furthermore, the provision of new pesticidal compounds with a higher efficacy strongly reduces the risk of appearance of resistant strains in the fungi to be treated. 25 We have now found a new family of compounds which show enhanced fungicidal activity over the general known family of such compounds. Accordingly, the present invention provides a N-[(trisubstitutedsilyl)methyl] carboxamide or its thiocarboxamide derivative of formula (I) Z ,Z 4 7 B Si N A z 1 z 2 z 5 z6T Z Z2 Z T 30 wherein WO 2011/151368 3 PCT/EP2011/059024 * A represents a carbo-linked, unsaturated or partially saturated, 5-membered heterocyclyl group that can be substituted by up to four groups R ; with the proviso that A is not a non-substituted 2 furyl ring ; * T represents 0 or S; 5 e n represents 0 or 1 * B represents a phenyl ring that can be susbtituted by up to 5 groups X which can be the same or different a naphthyl ring that can be susbtituted by up to 7 groups X which can be the same or different a thienyl ring that can be substituted by up to 3 groups X which can be the same or different or a benzothiophenyl ring that can be susbtituted by up to 5 groups X which can be the 10 same or different ; * X represents a halogen atom ; nitro ; cyano; isonitrile ; hydroxy ; amino ; sulfanyl ; pentafluoro-A6 sulfanyl ; formyl ; formyloxy ; formylamino ; substituted or non-substituted (hydroxyimino)-Cl-C 8 alkyl ; substituted or non-substituted (C 1
    -C
    8 -alkoxyimino)-C-C 8 -alkyl ; substituted or non substituted (C 2
    -C
    8 -alkenyloxyimino)-C-C 8 -alky ; substituted or non-substituted (C2-Cs 15 alkynyloxyimino)-C-C 8 -alkyl ; substituted or non-substituted (benzyloxyimino)-C-C 8 -alkyl ; carboxy ; carbamoyl ; N-hydroxycarbamoyl ; carbamate ; substituted or non-substituted Cl-Cs alkyl ; Cl-C8-halogenoalkyl having 1 to 5 halogen atoms ; substituted or non-substituted C2-Cs alkenyl ; C 2 -C8-halogenoalkenyl having 1 to 5 halogen atoms ; substituted or non-substituted C2 C8-alkynyl ; C 2 -C8-halogenoalkynyl having 1 to 5 halogen atoms ; substituted or non-substituted 20 Cl-C8-alkoxy; Cl-C8-halogenoalkoxy having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylsulfanyl ; Cl-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylsulfinyl ; Cl-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylsulfonyl ; Cl-C8-halogenoalkylsulfonyl having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylamino ; substituted or non-substituted 25 di-Cl-C8-alkylamino ; substituted or non-substituted C 2 -C8-alkenyloxy ; C 2 -C8-halogenoalkenyloxy having 1 to 5 halogen atoms ; substituted or non-substituted C 3 -C8-alkynyloxy ; C2-Cs halogenoalkynyloxy having 1 to 5 halogen atoms ; substituted or non-substituted C 3
    -C
    7 -cycloalkyl ; C 3
    -C
    7 -halogenocycloalkyl having 1 to 5 halogen atoms ; substituted or non-substituted (C3-C7 cycloalkyl)-Cl-C8-alkyl ; substituted or non-substituted (C 3
    -C
    7 -cycloalkyl)-C 2 -Cs-alkenyl ; 30 substituted or non-substituted (C 3
    -C
    7 -cycloalkyl)-C 2 -Cs-alkynyl ; substituted or non-substituted tri(Cl-Cs)alkylsilyl ; substituted or non-substituted tri(Cl-Cs)alkylsilyl-Cl-Cs-alky ; substituted or non-substituted Cl-C8-alkylcarbonyl ; Cl-C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylcarbonyloxy ; Cl-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylcarbonylamino ; Cl-C8 35 halogenoalkyl- carbonylamino having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8 alkoxycarbonyl ; Cl-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms ; substituted or non substituted Cl-C8-alkyloxycarbonyloxy ; Cl-C8-halogenoalkoxycarbonyloxy having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylcarbamoyl ; substituted or non-substituted di-Cl C8-alkylcarbamoyl ; substituted or non-substituted Cl-C8-alkylaminocarbonyloxy ; substituted or 40 non-substituted di-Cl-C8-alkylaminocarbonyloxy ; substituted or non-substituted N-(Cl-C8- WO 2011/151368 PCT/EP2011/059024 alkyl)hydroxy carbamoyl ; substituted or non-substituted C-C 8 -alkoxycarbamoy ; substituted or non-substituted N-(C-C 8 -alkyl)-C-C 8 -alkoxycarbamoy ; aryl that can be susbtituted by up to 6 groups Q which can be the same or different ; C-C 8 -arylalkyl that can be susbtituted by up to 6 groups Q which can be the same or different C 2
    -C
    8 -arylalkenyl that can be susbtituted by up to 6 5 groups Q which can be the same or different; C 2
    -C
    8 -arylalkynyl that can be susbtituted by up to 6 groups Q which can be the same or different ; aryloxy that can be susbtituted by up to 6 groups Q which can be the same or different ; arylsulfanyl that can be susbtituted by up to 6 groups Q which can be the same or different ; arylamino that can be susbtituted by up to 6 groups Q which can be the same or different ; C-C 8 -arylalkyloxy that can be susbtituted by up to 6 groups Q 10 which can be the same or different ; C-C 8 -arylalkylsulfanyl that can be susbtituted by up to 6 groups Q which can be the same or different ; or C-C 8 -arylalkylamino that can be susbtituted by up to 6 groups Q which can be the same or different ; * two substituent X together with the consecutive carbon atoms to which they are linked can form a 5- or 6-membered, saturated carbocycle or saturated heterocycle, which can be substituted by up 15 to four groups Q which can be the same or different ; e Z' and Z2 independently represent a hydrogen atom ; a halogen atom ; cyano ; substituted or non-substituted C-C 8 -alkyl ; C-C 8 -halogenoalkyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkoxy; substituted or non-substituted C-C 8 -alkylsulfanyl; or substituted or non-substituted C-C 8 -alkoxycarbonyl ; or Z' and Z2 are a C 2
    -C
    5 -alkylene group that can be 20 substituted by up to four C-C 8 -alkyl groups ; * Z 3 and Z 4 independently represent a substituted or non-substituted C-C 8 -alkyl; Z5 and Z6 independently represent a hydrogen atom ; a halogen atom ; cyano ; substituted or non-substituted C-C 8 -alkyl ; C-C 8 -halogenoalkyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkoxy; substituted or non-substituted C-C 8 -alkylsulfanyl; or substituted or 25 non-substituted C-C 8 -alkoxycarbonyl ; or Z5 and Z6 are a C 2
    -C
    5 -alkylene group that can be substituted by up to four C-C 8 -alkyl groups ; * Z 7 represents a hydrogen atom ; a formyl group; a substituted or non-substituted C-C 8 -alkyl ; a substituted or non substituted C-C 8 -alkoxy; a non-substituted C 3
    -C
    7 -cycloalkyl or a C3-C7 cycloalkyl substituted by up to 10 atoms or groups that can be the same or different and that can 30 be selected in the list consisting of halogen atoms, cyano, C-C 8 -alkyl, C-C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, C-C 8 -alkoxy, Cl-C8 halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different, Cl-C8 alkoxycarbonyl, C-C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different, C-C 8 -alkylaminocarbonyl and di-C-C 8 -alkylaminocarbonyl ; 35 e Q independently represents a halogen atom ; cyano ; nitro ; substituted or non-substituted Cl-C8 alkyl ; C-C 8 -halogenoalkyl having 1 to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 8 -alkoxy ; C-C 8 -halogenoalkoxy having 1 to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 8 -alkylsulfanyl ; Cl-C8 halogenoalkylsulfanyl having 1 to 9 halogen atoms that can be the same or different ; substituted 40 or non-substituted tri(C-C 8 )alkylsilyl ; substituted or non-substituted tri(C-C 8 )alkylsilyl-C-C 8 -alky WO 2011/151368 5 PCT/EP2011/059024 ; substituted or non-substituted (C 1
    -C
    8 -alkoxyimino)-C-C 8 -alkyl ; substituted or non-substituted (benzyloxyimino)-C-C 8 -alkyl ; R independently represents hydrogen atom ; halogen atom ; nitro ; cyano ; hydroxy ; amino sulfanyl ; pentafluoro-A 6 -sulfanyl ; substituted or non-substituted (C 1
    -C
    8 -alkoxyimino)-C-C 8 -alkyl 5 substituted or non-substituted (benzyloxyimino)-C-C 8 -alkyl ; substituted or non-substituted Cl-C8 alkyl ; C-C 8 -halogenoalkyl having 1 to 5 halogen atoms ; substituted or non-substituted C2-Cs alkenyl ; C 2
    -C
    8 -halogenoalkenyl having 1 to 5 halogen atoms ; substituted or non-substituted C2
    C
    8 -alkynyl ; C 2
    -C
    8 -halogenoalkynyl having 1 to 5 halogen atoms substituted or non-substituted
    C-C
    8 -alkoxy; C-C 8 -halogenoalkoxy having 1 to 5 halogen atoms substituted or non-substituted 10 C-C 8 -alkylsulfanyl ; C-C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkylsulfinyl ; C-C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkylsulfonyl ; C-C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkylamino ; substituted or non-substituted di-C-C 8 -alkylamino ; substituted or non-substituted C 2
    -C
    8 -alkenyloxy ; substituted or non 15 substituted C 3
    -C
    8 -alkynyloxy ; substituted or non-substituted C 3
    -C
    7 -cycloalkyl ; C3-C7 halogenocycloalkyl having 1 to 5 halogen atoms ; substituted or non-substituted tri(C-C 8 )alkylsilyl ; substituted or non-substituted C-C 8 -alkylcarbonyl ; C-C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms substituted or non-substituted C-C 8 -alkoxycarbonyl Cl-C8 halogenoalkoxycarbonyl having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8 20 alkylcarbamoyl ; substituted or non-substituted di-C-C 8 -alkylcarbamoyl ; phenoxy phenylsulfanyl ; phenylamino; benzyloxy; benzylsulfanyl ; or benzylamino; as well as its salts, N-oxydes, and optically active isomers. For the compounds according to the invention, the following generic terms are generally used with the 25 following meanings: * halogen means fluorine, bromine, chlorine or iodine. carboxy means -C(=O)OH; carbonyl means -C(=O)-; carbamoyl means -C(=O)NH 2 ; 30 N-hydroxycarbamoyl means -C(=O)NHOH; SO represents a sulfoxyde group;
    SO
    2 represents a sulfone group ; * an alkyl group, an alkenyl group and an alkynyl group as well as moieties containing these terms, can be linear or branched; 35 0 the aryl moeity contained in an aryl group, an arylalkyl group, an arylalkenyl group and an arylalkynyl group as well as moieties containing these terms, can be a phenyl group that can be substituted by up to 5 groups Q which can be the same or different, a naphthyl group that can be substituted by up to 7 groups Q which can be the same or different or a pyridyl group that can be substituted by up to 4 groups Q which can be the same or different; 40 e and, heteroatom means sulfur, nitrogen or oxygen.
    WO 2011/151368 6 PCT/EP2011/059024 * in the case of an amino group or the amino moiety of any other amino-comprising group, substituted by two substituent that can be the same or different, the two substituent together with the nitrogen atom to which they are linked can form a heterocyclyl group, preferably a 5- to 7 membered heterocyclyl group, that can be substituted or that can include other hetero atoms, for 5 example a morpholino group or piperidinyl group. * unless indicated otherwise, a group or a substituent that is substituted according to the invention can be substituted by one or more of the following groups or atoms: a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulfanyl group, a pentafluoro-k 6 sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N 10 hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C-C 6 -alkyl group, a C-C 8 -alkyl, a tri(C-C 8 -alkyl)silyl-C-C 8 -alkyl, C-C 8 -cycloalkyl, tri(C-C 8 -alkyl)silyl-C-C 8 -cycloalkyl, a Cl-C8 halogenoalkyl having 1 to 5 halogen atoms, a C-C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 2
    -C
    8 -alkenyl, a C 2
    -C
    8 -alkynyl, a C 2
    -C
    8 -alkenyloxy, a C 2
    -C
    8 -alkynyloxy, a Cl-C8 alkylamino, a di-C-C 8 -alkylamino, a C-C 8 -alkoxy, a C-C 8 -halogenoalkoxy having 1 to 5 halogen 15 atoms, a C-C 8 -alkylsulfanyl, a C-C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C2-Cs alkenyloxy, a C 2
    -C
    8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3
    -C
    8 -alkynyloxy, a C3
    C
    8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a Cl-C 8 -alkylcarbonyl, a Cl-C8 halogenoalkylcarbonyl having 1 to 5 halogen atoms, a Cl-C 8 -alkylcarbamoyl, a di-Cl-C 8 alkylcarbamoyl, a N-Cl-C 8 -alkyloxycarbamoyl, a Cl-C 8 -alkoxycarbamoyl, a N-Cj-C 8 -alkyl-Cj-C 8 20 alkoxycarbamoyl, a Cl-C 8 -alkoxycarbonyl, a Cl-C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a Cl-C 8 -alkylcarbonyloxy, a Cl-C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a Cl-C 8 -alkylcarbonylamino, a Cl-C-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a Cl-C 8 -alkylaminocarbonyloxy, a di-Cl-C 8 -alkylaminocarbonyloxy, a Cl-C 8 -alkyloxycarbonyloxy, a Cl-C 8 -alkylsulfinyl, a Cl-C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a Cl-C8 25 alkylsulfonyl, a Cl-C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, a Cl-C8 alkylaminosulfamoyl, a di-Cl-C 8 -alkylaminosulfamoyl, a (Cl-C 6 -alkoxyimino)-Cl-C 6 -alkyl, a (C-C6 alkenyloxyimino)-Cl-C 6 -alkyl, a (Cl-C 6 -alkynyloxyimino)-Cl-C 6 -alkyl, a 2-oxopyrrolidin-1-yl, (benzyloxyimino)-Cl-C 6 -alkyl, Cl-C 8 -alkoxyalkyl, Cl-C 8 -halogenoalkoxyalkyl having 1 to 5 halogen atoms, benzyloxy, benzylsulfanyl, benzylamino, phenoxy, phenylsulfanyl, or phenylamino. 30 Any of the compounds of the present invention can exist in one or more optical or chiral isomer forms depending on the number of asymmetric centres in the compound. The invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic" denotes a mixture of enantiomers in different proportions) and to the mixtures of all the possible stereoisomers, in all 35 proportions. The diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by the man ordinary skilled in the art. Any of the compounds of the present invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions. The geometric isomers can be 40 separated according to general methods, which are known per se by the man ordinary skilled in the art. Any of the compounds of the present invention can also exist in one or more geometric isomer forms depending on the relative position (syn/anti or cis/trans) of the substituents of ring B. The invention thus WO 2011/151368 PCT/EP2011/059024 relates equally to all syn/anti (or cis/trans) isomers and to all possible syn/anti (or cis/trans) mixtures, in all proportions. The syn/anti (or cis/trans) isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art. Any of the compounds of formula (I) wherein X represents a hydroxy, a sulfanyl group or an amino group 5 may be found in its tautomeric form resulting from the shift of the proton of said hydroxy, sulfanyl or amino group. Such tautomeric forms of such compounds are also part of the present invention. More generally speaking, all tautomeric forms of compounds of formula (I) wherein X represents a hydroxy, a sulfanyl group or an amino group, as well as the tautomeric forms of the compounds which can optionally be used as intermediates in the preparation processes and which will be defined in the description of these 10 processes, are also part of the present invention. Preferred compounds according to the invention are compounds of formula (I) wherein A is selected in the list consisting of: - a heterocycle of formula (A 1 ) R2 R1 R R 15 R3
    (A
    1 ) wherein R1 to R3 that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same 20 or different ; substituted or non-substituted C-C 5 -alkoxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; providing that a least one of the substituent R 1 to R 3 is not a hydrogen atom ; - a heterocycle of formula (A 2 ) R 6 RSR 25 0
    (A
    2 ) wherein R4 to R6 that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same 30 or different ; substituted or non-substituted C-C 5 -alkoxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; - a heterocycle of formula (A 3
    )
    WO 2011/151368 8 PCT/EP2011/059024 R/ N N N
    R
    8
    (A
    3 ) wherein
    R
    7 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; Cl-Cs 5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non substituted C-C 5 -alkoxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; R represents a hydrogen atom or a substituted or non-substituted C-C 5 -alkyl; 10 - a heterocycle of formula (A 4 ) R 10 R1 R S
    (A
    4 ) wherein R9 to R" that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 15 non-substituted C-C 5 -alkyl ; amino ; substituted or non-substituted C-C 5 -alkoxy ; substituted or non substituted C-C 5 -alkylsulfanyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; 20 - a heterocycle of formula (A 5 ) /
    (A
    5 ) wherein R and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 25 non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy ; amino ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; R14 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy; amino ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can 30 be the same or different or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; WO 2011/151368 PCT/EP2011/059024 - a heterocycle of formula (A 6 ) R 16 R'/ N R1 17
    (A
    6 ) 5 wherein
    R
    15 represents a hydrogen atom ; a halogen atom ; a cyano ; substituted or non-substituted C-C 5 -alkyl substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; 10 R16 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkoxycarbonyl ; substituted or non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ;
    R
    17 represent a hydrogen atom or substituted or non-substituted C-C 5 -alkyl 15 - a heterocycle of formula (A 7 ) R22 R21 R R 2 N R" 19 R
    (A
    7 ) wherein 20 R 19 represents a hydrogen atom or a C-C 5 -alkyl R to R that can be the same or different represent a hydrogen atom a halogen atom substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; 25 - a heterocycle of formula (A 8 ) R 2 N R24, R (A 8 ) wherein
    R
    23 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-C5 30 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; WO 2011/151368 10 PCT/EP2011/059024 R represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; - a heterocycle of formula (A 9 ) N R26 R2 Re RM 5 0
    (A
    9 ) wherein
    R
    25 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; 10 R represents a hydrogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; - a heterocycle of formula (A 10 ) N R282 R S 15 (A 1 0 ) wherein
    R
    27 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; Cl-C5 20 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; amino ; substituted or non substituted C-C 5 -alkylamino or substituted or non-substituted di(C-C 5 -alkyl)amino; - a heterocycle of formula (All) N R30 R29 25 S (A 1) wherein R 2 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the 30 same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; C-C 5 -halogenoalkoxy WO 2011/151368 11 PCT/EP2011/059024 comprising up to 9 halogen atoms that can be the same or different ; amino substituted or non substituted C-C 5 -alkylamino or substituted or non-substituted di(C-C 5 -alkyl)amino; - a heterocycle of formula (A 12 ) R 3 R N N N 5 R
    (A
    12 ) wherein
    R
    31 represents a hydrogen atom or a substituted or non-substituted C-C 5 -alkyl
    R
    32 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C1-C5 10 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ;
    R
    33 represents a hydrogen atom ; a halogen atom ; a nitro ; substituted or non-substituted C-C 5 -alkyl substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; 15 - a heterocycle of formula (A 13 ) / N R 35) ,N R3 N 1 36
    (A
    13 ) wherein 20 R 3 4 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted or non-substituted C 3
    -C
    5 -cycloalkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 5 -alkoxy ; substituted or non-substituted C2-C5 alkynyloxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
    R
    3 5 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; a cyano 25 substituted or non-substituted C-C 5 -alkoxy ; substituted or non-substituted C-C 5 -alkylsulfanyl ; C1-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; amino ; substituted or non substituted C-C 5 -alkylamino or substituted or non-substituted di(C-C 5 -alkyl)amino; R 3 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl; 30 -a heterocycle of formula (A 14
    )
    WO 2011/151368 12 PCT/EP2011/059024 R38 R37 Rs R N N 139
    (A
    14 ) wherein R 3 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 5 non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different substituted or non-substituted C-C 5 -alkoxy or a substituted or non-substituted C1-Cs alkylsulfanyl
    R
    3 9 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl 10 - a heterocycle of formula (A 15 ) R 41 N/
    (A
    15 ) wherein R and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 15 non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; - a heterocycle of formula (A 16 ) R 42 N/ 20 (A16) wherein R42 and R43 that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or amino 25 -a heterocycle of formula (A 17 ) R 45 R 44 N'* 0
    (A
    17 ) wherein WO 2011/151368 13 PCT/EP2011/059024 R44 and R45 that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; 5 - a heterocycle of formula (A 18 ) R47 N/ N S R 4 6
    (A
    18 ) wherein
    R
    4 7 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-C5 10 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ;
    R
    4 6 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ;C-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or substituted or non substituted C-C 5 -alkylsulfanyl 15 - a heterocycle of formula (A 19 ) R49 R48 R4 R4 S
    (A
    1 9) wherein R49 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 20 non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different - a heterocycle of formula (A 20 ) 25
    R
    5 0 S
    (A
    20 ) wherein R and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 30 non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different -a heterocycle of formula (A 21
    )
    WO 2011/151368 14 PCT/EP2011/059024
    R
    5 2 N N S
    (A
    21 ) wherein
    R
    52 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-Cs 5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different. -a heterocycle of formula (A 22 ) R 5 N N S
    (A
    22 ) 10 wherein
    R
    53 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-Cs halogenoalkyl comprising up to 9 halogen atoms that can be the same or different. -a heterocycle of formula (A 23 ) R 54 N NR 15 R
    (A
    23 ) wherein R54 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the 20 same or different ;
    R
    55 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl -a heterocycle of formula (A 24 ) R57 N N,,, R 25
    (A
    24 ) wherein WO 2011/151368 15 PCT/EP2011/059024 R 5 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ;
    R
    58 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl 5 -a heterocycle of formula (A 25 ) R60 R61 RG RS N N R62 (A 25) wherein 10 R60 and R61 that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R62 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl; 15 -a heterocycle of formula (A 26 )
    R
    65 R63 NN 164 R R (2e (A 26) wherein R 6 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted 20 or non-substituted C 3
    -C
    5 -cycloalkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 5 -alkoxy ; substituted or non-substituted C2-Cs alkynyloxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R 6 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; a cyano substituted or non-substituted C-C 5 -alkoxy ; substituted or non-substituted C-C 5 -alkylsulfanyl ; Cl-C5 25 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; amino ; substituted or non substituted C-C 5 -alkylamino or di(C-Cs-alkyl)amino; R64 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl. 30 More preferred compounds according to the invention are compounds of formula (I) wherein A is selected in the list consisting of A 2 ; A 6 ; A 1 0 and A 13 as herein-defined. Even more preferred compounds according to the invention are compounds of formula (I) wherein A represents A wherein R34 represents a substituted or non-substituted C-C 5 -alkyl, C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non-substituted Cl-Cs- WO 2011/151368 16 PCT/EP2011/059024 alkoxy ; R35 represents a hydrogen atom or a halogen atom and R represents a substituted or non substituted C-C 5 -alkyl. Other preferred compounds according to the invention are compounds of formula (I) wherein T represents 5 0. Other preferred compounds according to the invention are compounds of formula (I) wherein B represents a substituted or non-substituted phenyl ring or a substituted or non-substituted naphthyl ring. Even more preferably, B represents a substituted or non-substituted phenyl ring. 10 Other preferred compounds according to the invention are compounds of formula (I) wherein X independently represents a halogen atom ; substituted or non-substituted C-C 8 -alkyl ; Cl-C8 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non substituted tri(C-C 8 -alkyl)silyl ; substituted or non-substituted C-C 8 -alkoxy or C-C 8 -halogenoalkoxy 15 comprising up to 9 halogen atoms that can be the same or different; or wherein two consecutive substituents X together with the phenyl ring form a substituted or non substituted 1,3-benzodioxolyl ; 1,2,3,4-tetrahydro-quinoxalinyl ; 3,4-dihydro-2H-1,4-benzoxazinyl ; 1,4-benzodioxanyl ; indanyl ; 2,3 dihydrobenzofuranyl ; or indolinyl. 20 Other preferred compounds according to the invention are compounds of formula (I) wherein Z 1 , Z2, Z 5 and Z6 independently represent a hydrogen atom, a substituted or non-substituted C-C 8 -alkyl or a substituted or non-substituted C-C 8 -alkoxy. Other preferred compounds according to the invention are compounds of formula (I) wherein Z 3 and Z 4 25 independently represent a non-substituted C-C 8 -alkyl. More preferably, Z 3 and Z 4 independently represent a non-substituted C-C 3 -alkyl. Even more preferably, Z 3 and Z 4 represent methyl. Other preferred compounds according to the invention are compounds of formula (I) wherein Z 7 represents a hydrogen atom, a non-substituted C3-C7 cycloalkyl or a C3-C7 cycloalkyl substituted by up to 30 10 groups or atoms that can be the same or different and that can be selected in the list consisting of halogen atoms, C-C 8 -alkyl, C-C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, C-C 8 -alkoxy or C-C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different. More preferably Z7 represents a non-substituted C 3
    -C
    7 -cycloalkyl ; even more preferably Z 7 represents cyclopropyl. 35 Other preferred compounds according to the invention are compounds of formula (I) wherein R independently represents a hydrogen atom ; halogen atom ; cyano ; substituted or non-substituted Cl-C8 alkylamino ; substituted or non-substituted di-C-C 8 -alkylamino ; substituted or non-substituted tri(C-C 8 alkyl)silyl ; substituted or non-substituted C-C 8 -alkyl ; C-C 8 -halogenoalkyl comprising up to 9 halogen 40 atoms that can be the same or different ; substituted or non-substituted C-C 8 -alkoxy ; Cl-C8 halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; substituted or non- WO 2011/151368 17 PCT/EP2011/059024 substituted C-C 8 -alkylsulfanyl ; amino ; hydroxyl ; nitro ; substituted or non-substituted C1-Cs alkoxycarbonyl ; substituted or non-substituted C 2
    -C
    8 -alkynyloxy. The above mentioned preferences with regard to the substituents of the compounds according to the 5 invention can be combined in various manners. These combinations of preferred features thus provide sub-classes of compounds according to the invention. Examples of such sub-classes of preferred compounds according to the invention can be combined: - preferred features of A with preferred features of B, Z1, Z2, Z3, Z4, Z5, Z6, Z7, X, T and R; - preferred features of B with preferred features of A, Z1, Z2, Z3, Z4, Z5, Z6, Z7, X, T and R; 10 - preferred features of Z1 with preferred features of A, B, Z2, Z3, Z4, Z5, Z6, Z7, X, T and R; - preferred features of Z2 with preferred features of A, B, Z1, Z3, Z4, Z5, Z6, Z7, X, T and R; - preferred features of Z3 with preferred features of A, B, Z 3, Z2, Z4, Z5, Z6, Z7, X, T and R; - preferred features of Z4 with preferred features of A, B, Z1, Z2, Z3, Z5, Z6, Z7, X, T and R; - preferred features of Z5 with preferred features of A, B, Z1, Z2, Z3, Z4, Z6, Z, X, T and R; 15 - preferred features of Z6 with preferred features of A, B, Z1, Z2, Z3, Z4, Z5, Z7, X, T and R; - preferred features of Z7 with preferred features of A, B, Z1, Z2, Z3, Z4, Z5, Z, X, T and R; - preferred features of X with preferred features of A, B, Z1, Z2, Z3, Z4, Z5 , Z Z7 , T and R; - preferred features of T with preferred features of A, B, Z1, Z2, Z3, Z4, Z5, Z6, Z7, X and R; - preferred features of R with preferred features of A, B, Z1, Z2, Z3, Z4, Z5, Z6, Z, T and X; 20 In these combinations of preferred features of the substituents of the compounds according to the invention, the said preferred features can also be selected among the more preferred features of each of A, B, Z , Z2, Z3, Z4, Z5, Z, Z, T and X, so as to form most preferred subclasses of compounds according to the invention. 25 The present invention also relates to a process for the preparation of the compound of formula (1). Thus, according to a further aspect of the present invention there is provided a process P1 for the preparation of a compound of formula () as herein-defined and wherein T represents O and that 20 Inwhese Bcin a Z2, Z rered, Zfa re of therein derivative of the opon oding tolthe L i A 1 2 3 4 55 6 7 Aeei B, Z n ,Z, Z, Z2, Z3, Z4 , and ,7s asofrm os pre-eferred; subcaesofylcpu acidringo Theoresent ineto(lseae1o1)rcs:ortepearto fte opudo frua() wherein A is as herein-defined and Lw represents a leaving group selected in the list consisting of a 35 halogen atom, a hydroxyl group, -OR , -OC(=0)Ra, Ra being a substituted or non-substituted C-C-alkyl, a substituted or non-substituted Cl-Ce-haloalkyl, a benzyl, 4-methoxybenzyl or pentafluorophenyl group, WO 2011/151368 18 PCT/EP2011/059024 or a group of formula O-C(=O)A; in the presence of a catalyst and in the presence of a condensing agent in case Ll represents a hydroxyl group, and in the presence of an acid binder in case Ll represents a halogen atom. 5 N-[(trisubstitutedsilyl)methyl]amine derivatives of formula (II) wherein Z7 is a substituted or non substituted Cl-C 8 -alkyl or a substituted or non-substituted C 3
    -C
    7 -cycloalkyl, can be prepared by known processes such as the nucleophilic substitution of a (halogenomethyl)-(dialkyl)arylsilane by the corresponding primary amine (Journal of Organometallic Chemistry (1978), 153, 193). N [(trisubstitutedsilyl)methyl]amine derivatives of formula (II) wherein Z 7 is a hydrogen atom can be 10 prepared by known processes such as the nucleophilic substitution of a (halogenomethyl)(dialkyl)arylsilane by ammonia (Journal of the Americam Chemical Society (1951), 73, 3867) or by phthalimide followed a deprotection by hydrazine (patent application EP0291787). Furthermore N-[(trisubstitutedsilyl)methyl]amine derivatives of formula (II) wherein Z7 is a substituted or non-substituted Cl-C 8 -alkyl or a substituted or non-substituted C 3
    -C
    7 -cycloalkyl, can be prepared by 15 known processes from N-[(trisubstitutedsilyl)methyl]amine derivatives of formula (II) wherein Z7 is a hydrogen atom by reductive amination with an aldehyde or ketone, or by nucleophilic substitution of a halogeno(cyclo)alkyl (Journal of Organic Chemistry (2005), 70, 8372). Carboxylic acid derivatives of formula (Ill) can be prepared by known processes. 20 In case Ll represents a hydroxy group, the process according to the present invention is conducted in the presence of condensing agent. Suitable condensing agent may be selected in the non limited list consisting of acid halide former, such as phosgene, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide or thionyl chloride; anhydride former, such as 25 ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as N,N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorous pentoxide, polyphosphoric acid, N,N'-carbonyl diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine/tetrachloro methane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate or bromo 30 tripyrrolidino-phosphonium-hexafluorophosphate. The process according to the present invention is conducted in the presence of a catalyst. Suitable catalyst may be selected in the list consisting of 4-dimethyl-aminopyridine, 1-hydroxy-benzotriazole or dimethylformamide. 35 In case Ll represents a halogen atom, the process according to the present invention is conducted in the presence of an acid binder. Suitable acid binders for carrying out process P1 according to the invention are in each case all inorganic and organic bases that are customary for such reactions. Preference is given to using alkaline earth metal, alkali metal hydride, alkali metal hydroxides or alkali metal alkoxides, such as sodium hydroxide, sodium hydride, calcium hydroxide, potassium hydroxide, potassium tert 40 butoxide or other ammonium hydroxide, alkali metal carbonates, such as cesium carbonate, sodium WO 2011/151368 19 PCT/EP2011/059024 carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetateand also tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclo 5 nonene (DBN) or diazabicycloundecene (DBU). It is also possible to work in the absence of an additional condensing agent or to employ an excess of the amine component, so that it simultaneously acts as acid binder agent. According to a further aspect according to the invention, there is provided a process P2 for the 10 preparation of a compound of formula (I) wherein T represents S, starting from a compound of formula (I) wherein T represents 0 and illustrated according to the following reaction scheme Zkz z 7 Z Zi ,Z4 IZ ,Z/4 B Si N A th B Si N A 'Xz yo hbnating S2 6 agent Z Z Scheme P2 15 wherein A, B, n, Z1, Z2, Z3, Z4, Z5, Z6 and Z7 are as herein-defined, in the optional presence of a catalytic or stoechiometric or more, quantity of a base such as an inorganic and organic base. Preference is given to using alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate ; heterocyclic aromatic bases, such as pyridine, picoline, lutidine, collidine ; and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N 20 dimethylaniline, N,N-dimethylaminopyridine or N-methyl-piperidine. Process P2 according to the invention is performed in the presence of a thionating agent. Starting amide derivatives of formula (I) can be prepared according to processes P1. 25 Suitable thionating agents for carrying out process P2 according to the invention can be sulfur (S), sulfhydric acid (H 2 S), sodium sulfide (Na 2 S), sodium hydrosulfide (NaHS), boron trisulfide (B 2 5 3 ), bis(diethylaluminium) sulfide ((AIEt 2
    )
    2 S), ammonium sulfide ((NH 4
    )
    2 S), phosphorous pentasulfide (P 2 S5), Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) or a polymer 30 supported thionating reagent such as described in Journal of the Chemical Society, Perkin 1 (2001), 358. The compound according to the present invention can be prepared according to the general processes of preparation described above. It will nevertheless be understood that, on the basis of his general knowledge and of available publications, the skilled worker will be able to adapt this method according to 35 the specifics of each of the compounds, which it is desired to synthesize. Still in a further aspect, the present invention relates to compounds of formula (II) useful as intermediate compounds or materials for the process of preparation according to the invention.
    WO 2011/151368 20 PCT/EP2011/059024 The present invention thus provides compounds of formula (II): Z ,Z 4 H B Si Z Z n2 Z z 1 z 2 z5 z6 (II) wherein B, n, Z1, Z2, Z3, Z4, Z5 and Z6 are as herein-defined, and Z 7 represents a cyclopropyl, cyclobutyl, 5 cyclopentyl, cyclohexyl or cycloheptyl group with the exclusion of N-{[dimethyl (phenyl)silyl]methyl}cyclohexanamine. On the basis of the present description and his general knowledge and of available publications as for example Journal of Organometallic Chemistry (1978), 153, 193 or Journal of Organic Chemistry (2005), 10 70, 8372, the skilled person can prepare intermediate compound of formula (II) according to the present invention. In a further aspect, the present invention also relates to a fungicide composition comprising an effective and non-phytotoxic amount of an active compound of formula (I). 15 The expression "effective and non-phytotoxic amount" means an amount of composition according to the invention that is sufficient to control or destroy the fungi present or liable to appear on the cropsand that does not entail any appreciable symptom of phytotoxicity for the said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the climatic conditions and the compounds included in the fungicide composition according to the invention. This amount can be 20 determined by systematic field trials that are within the capabilities of a person skilled in the art. Thus, according to the invention, there is provided a fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) as herein defined and an agriculturally acceptable support, carrier or filler. 25 According to the invention, the term "support" denotes a natural or synthetic, organic or inorganic compound with that the active compound of formula (I) is combined or associated to make it easier to apply, notably to the parts of the plant. This support is thus generally inert and should be agriculturally acceptable. The support can be a solid or a liquid. Examples of suitable supports include clays, natural or 30 synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol, organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports can also be used. The composition according to the invention can also comprise additional components. In particular, the composition can further comprise a surfactant. The surfactant can be an emulsifier, a dispersing agent or 35 a wetting agent of ionic or non-ionic type or a mixture of such surfactants. Mention can be made, for example, of polyacrylic acid salts, lignosulfonic acid salts, phenolsulfonic or naphthalenesulfonic acid salts, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in particular alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine WO 2011/151368 21 PCT/EP2011/059024 derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated alcohols or phenols, fatty acid esters of polyolsand derivatives of the above compounds containing sulfate, sulfonate and phosphate functions. The presence of at least one surfactant is generally essential when the active compound and/or the inert support are water-insoluble and when the vector agent for the application is 5 water. Preferably, surfactant content can be comprised from 5% to 40% by weight of the composition. Optionally, additional components can also be included, e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents. More generally, the active compounds can be combined with any solid or liquid additive, that complies with the usual formulation 10 techniques. In general, the composition according to the invention can contain from 0.05 to 99% by weight of active compound, preferably 10 to 70% by weight. 15 Compositions according to the invention can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure),gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for 20 dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ULV) liquid, ultra low volume (ULV) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder. These compositions include not only compositions that are ready to be applied to the plant or seed to be treated 25 by means of a suitable device, such as a spraying or dusting device, but also concentrated commercial compositions that must be diluted before application to the crop. The compounds according to the invention can also be mixed with one or more insecticide, fungicide, bactericide, attractant, acaricide or pheromone active substance or other compounds with biological 30 activity. The mixtures thus obtained have normally a broadened spectrum of activity. The mixtures with other fungicide compounds are particularly advantageous. Examples of suitable fungicide mixing partners can be selected in the following lists: (1) Inhibitors of the ergosterol biosynthesis, for example (1.1) aldimorph (1704-28-5), (1.2) azaconazole (60207-31-0), (1.3) bitertanol (55179-31-2), (1.4) bromuconazole (116255-48-2), (1.5) cyproconazole 35 (113096-99-4), (1.6) diclobutrazole (75736-33-3), (1.7) difenoconazole (119446-68-3), (1.8) diniconazole (83657-24-3), (1.9) diniconazole-M (83657-18-5), (1.10) dodemorph (1593-77-7), (1.11) dodemorph acetate (31717-87-0), (1.12) epoxiconazole (106325-08-0), (1.13) etaconazole (60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole (114369-43-6), (1.16) fenhexamid (126833-17-8), (1.17) fenpropidin (67306-00-7), (1.18) fenpropimorph (67306-03-0), (1.19) fluquinconazole (136426-54-5), 40 (1.20) flurprimidol (56425-91-3), (1.21) flusilazole (85509-19-9), (1.22) flutriafol (76674-21-0), (1.23) furconazole (112839-33-5), (1.24) furconazole-cis (112839-32-4), (1.25) hexaconazole (79983-71-4), (1.26) imazalil (60534-80-7), (1.27) imazalil sulfate (58594-72-2), (1.28) imibenconazole (86598-92-7), WO 2011/151368 22 PCT/EP2011/059024 (1.29) ipconazole (125225-28-7), (1.30) metconazole (125116-23-6), (1.31) myclobutanil (88671-89-0), (1.32) naftifine (65472-88-0), (1.33) nuarimol (63284-71-9), (1.34) oxpoconazole (174212-12-5), (1.35) paclobutrazol (76738-62-0), (1.36) pefurazoate (101903-30-4), (1.37) penconazole (66246-88-6), (1.38) piperalin (3478-94-2), (1.39) prochloraz (67747-09-5), (1.40) propiconazole (60207-90-1), (1.41) 5 prothioconazole (178928-70-6), (1.42) pyributicarb (88678-67-5), (1.43) pyrifenox (88283-41-4), (1.44) quinconazole (103970-75-8), (1.45) simeconazole (149508-90-7), (1.46) spiroxamine (118134-30-8), (1.47) tebuconazole (107534-96-3), (1.48) terbinafine (91161-71-6), (1.49) tetraconazole (112281-77-3), (1.50) triadimefon (43121-43-3), (1.51) triadimenol (89482-17-7), (1.52) tridemorph (81412-43-3), (1.53) triflumizole (68694-11-1), (1.54) triforine (26644-46-2), (1.55) triticonazole (131983-72-7), (1.56) 10 uniconazole (83657-22-1), (1.57) uniconazole-p (83657-17-4), (1.58) viniconazole (77174-66-4), (1.59) voriconazole (137234-62-9), (1.60) 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol (129586-32 9), (1.61) methyl 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-lH-imidazole-5-carboxylate (110323-95-0), (1.62) N'-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N methylimidoformamide, (1.63) N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3 15 (trimethylsilyl)propoxy]phenyl}imidoformamide and (1.64) O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2 yl] 1 H-imidazole-1 -carbothioate (111226-71-2). (2) inhibitors of the respiratory chain at complex I or II, for example (2.1) bixafen (581809-46-3), (2.2) boscalid (188425-85-6), (2.3) carboxin (5234-68-4), (2.4) diflumetorim (130339-07-0), (2.5) fenfuram 20 (24691-80-3), (2.6) fluopyram (658066-35-4), (2.7) flutolanil (66332-96-5), (2.8) fluxapyroxad (907204-31 3), (2.9) furametpyr (123572-88-3), (2.10) furmecyclox (60568-05-0), (2.11) isopyrazam (mixture of syn epimeric racemate 1 RS,4SR,9RS and anti-epimeric racemate 1 RS,4SR,9SR) (881685-58-1), (2.12) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.13) isopyrazam (anti-epimeric enantiomer 1 R,4S,9S), (2.14) isopyrazam (anti-epimeric enantiomer 1 S,4R,9R), (2.15) isopyrazam (syn epimeric 25 racemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18) mepronil (55814-41-0), (2.19) oxycarboxin (5259-88-1), (2.20) penflufen (494793-67-8), (2.21) penthiopyrad (183675-82-3), (2.22) sedaxane (874967-67-6), (2.23) thifluzamide (130000-40-7), (2.24) 1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3 (trifluoromethyl)-1H-pyrazole-4-carboxamide, (2.25) 3-(difluoromethyl)-1 -methyl-N-[2-(1,1,2,2 30 tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide, (2.26) 3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3 hexafluoropropoxy)phenyl]-1 -methyl-1 H-pyrazole-4-carboxamide, (2.27) N-[1-(2,4-dichlorophenyl)-1 m ethoxypropan-2-yl]-3-(d ifluoromethyl)- 1-methyl-1H-pyrazole-4-carboxamide (1092400-95-7) (WO 2008148570), (2.28) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2 yl]oxy}phenyl)ethyl]quinazolin-4-amine (1210070-84-0) (W02010025451) and (2.29) N-[9 35 (dichloromethylene)- 1,2,3,4-tetrahydro- 1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1 -methyl-1 H pyrazole-4-carboxamide. (3) inhibitors of the respiratory chain at complex Ill, for example (3.1) ametoctradin (865318-97-4), (3.2) amisulbrom (348635-87-0), (3.3) azoxystrobin (131860-33-8), (3.4) cyazofamid (120116-88-3), (3.5) 40 coumethoxystrobin (850881-30-0), (3.6) coumoxystrobin (850881-70-8), (3.7) dimoxystrobin (141600-52 4), (3.8) enestroburin (238410-11-2) (WO 2004/058723), (3.9) famoxadone (131807-57-3) (WO 2004/058723), (3.10) fenamidone (161326-34-7) (WO 2004/058723), (3.11) fenoxystrobin (918162-02-4), WO 2011/151368 23 PCT/EP2011/059024 (3.12) fluoxastrobin (361377-29-9) (WO 2004/058723), (3.13) kresoxim-methyl (143390-89-0) (WO 2004/058723), (3.14) metominostrobin (133408-50-1) (WO 2004/058723), (3.15) orysastrobin (189892 69-1) (WO 2004/058723), (3.16) picoxystrobin (117428-22-5) (WO 2004/058723), (3.17) pyraclostrobin (175013-18-0) (WO 2004/058723), (3.18) pyrametostrobin (915410-70-7) (WO 2004/058723), (3.19) 5 pyraoxystrobin (862588-11-2) (WO 2004/058723), (3.20) pyribencarb (799247-52-2) (WO 2004/058723), (3.21) triclopyricarb (902760-40-1), (3.22) trifloxystrobin (141517-21-7) (WO 2004/058723), (3.23) (2E)-2 (2-{[6-(3-chloro-2-m ethylphenoxy)-5-fluoropyrimid in-4-yl]oxy}phenyl)-2-(m ethoxyimi no)-N methylethanamide (WO 2004/058723), (3.24) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1 E)-1 -[3 (trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide (WO 2004/058723), (3.25) (2E) 10 2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3 (trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide (158169-73-4), (3.26) (2E)-2-{2-[({[(1 E)-1 (3-{[(E)-1 -fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N methylethanamide (326896-28-0), (3.27) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2 ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, (3.28) 2-chloro-N-(1,1,3 15 trimethyl-2,3-dihydro-1 H-inden-4-yl)pyridine-3-carboxamide (119899-14-8), (3.29) 5-methoxy-2-methyl-4 (2-{[({(1 E)-1 -[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1, 2,4-triazol 3-one, (3.30) methyl (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3 methoxyprop-2-enoate (149601-03-6), (3.31) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2 hydroxybenzamide (226551-21-9), (3.32) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N 20 methylacetamide (173662-97-0) and (3.33) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N methylacetamide (394657-24-0). (4) Inhibitors of the mitosis and cell division, for example (4.1) benomyl (17804-35-2), (4.2) carbendazim (10605-21-7), (4.3) chlorfenazole (3574-96-7), (4.4) diethofencarb (87130-20-9), (4.5) ethaboxam 25 (162650-77-3), (4.6) fluopicolide (239110-15-7), (4.7) fuberidazole (3878-19-1), (4.8) pencycuron (66063 05-6), (4.9) thiabendazole (148-79-8), (4.10) thiophanate-methyl (23564-05-8), (4.11) thiophanate (23564-06-9), (4.12) zoxamide (156052-68-5), (4.13) 5-chloro-7-(4-methylpiperid in-1-yl)-6-(2,4,6 trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine (214706-53-3) and (4.14) 3-chloro-5-(6-chloropyridin-3-yl) 6-methyl-4-(2,4,6-trifluorophenyl)pyridazine (1002756-87-7). 30 (5) Compounds capable to have a multisite action, like for example (5.1) bordeaux mixture (8011-63-0), (5.2) captafol (2425-06-1), (5.3) captan (133-06-2) (WO 02/12172), (5.4) chlorothalonil (1897-45-6), (5.5) copper hydroxide (20427-59-2), (5.6) copper naphthenate (1338-02-9), (5.7) copper oxide (1317-39-1), (5.8) copper oxychloride (1332-40-7), (5.9) copper(2+) sulfate (7758-98-7), (5.10) dichlofluanid (1085-98 35 9), (5.11) dithianon (3347-22-6), (5.12) dodine (2439-10-3), (5.13) dodine free base, (5.14) ferbam (14484-64-1), (5.15) fluorofolpet (719-96-0), (5.16) folpet (133-07-3), (5.17) guazatine (108173-90-6), (5.18) guazatine acetate, (5.19) iminoctadine (13516-27-3), (5.20) iminoctadine albesilate (169202-06-6), (5.21) iminoctadine triacetate (57520-17-9), (5.22) mancopper (53988-93-5), (5.23) mancozeb (8018-01 7), (5.24) maneb (12427-38-2), (5.25) metiram (9006-42-2), (5.26) metiram zinc (9006-42-2), (5.27) 40 oxine-copper (10380-28-6), (5.28) propamidine (104-32-5), (5.29) propineb (12071-83-9), (5.30) sulphur and sulphur preparations including calcium polysulphide (7704-34-9), (5.31) thiram (137-26-8), (5.32) tolylfluanid (731-27-1), (5.33) zineb (12122-67-7) and (5.34) ziram (137-30-4).
    WO 2011/151368 24 PCT/EP2011/059024 (6) Compounds capable to induce a host defence, like for example (6.1) acibenzolar-S-methyl (135158 54-2), (6.2) isotianil (224049-04-1), (6.3) probenazole (27605-76-1) and (6.4) tiadinil (223580-51-6). 5 (7) Inhibitors of the amino acid and/or protein biosynthesis, for example (7.1) andoprim (23951-85-1), (7.2) blasticidin-S (2079-00-7), (7.3) cyprodinil (121552-61-2), (7.4) kasugamycin (6980-18-3), (7.5) kasugamycin hydrochloride hydrate (19408-46-9), (7.6) mepanipyrim (110235-47-7), (7.7) pyrimethanil (53112-28-0) and (7.8) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline (861647-32-7) (W02005070917). 10 (8) Inhibitors of the ATP production, for example (8.1) fentin acetate (900-95-8), (8.2) fentin chloride (639 58-7), (8.3) fentin hydroxide (76-87-9) and (8.4) silthiofam (175217-20-6). (9) Inhibitors of the cell wall synthesis, for example (9.1) benthiavalicarb (177406-68-7), (9.2) 15 dimethomorph (110488-70-5), (9.3) flumorph (211867-47-9), (9.4) iprovalicarb (140923-17-7), (9.5) mandipropamid (374726-62-2), (9.6) polyoxins (11113-80-7), (9.7) polyoxorim (22976-86-9), (9.8) validamycin A (37248-47-8) and (9.9) valifenalate (283159-94-4; 283159-90-0). (10) Inhibitors of the lipid and membrane synthesis, for example (10.1) biphenyl (92-52-4), (10.2) 20 chloroneb (2675-77-6), (10.3) dicloran (99-30-9), (10.4) edifenphos (17109-49-8), (10.5) etridiazole (2593-15-9), (10.6) iodocarb (55406-53-6), (10.7) iprobenfos (26087-47-8), (10.8) isoprothiolane (50512 35-1), (10.9) propamocarb (25606-41-1), (10.10) propamocarb hydrochloride (25606-41-1), (10.11) prothiocarb (19622-08-3), (10.12) pyrazophos (13457-18-6), (10.13) quintozene (82-68-8), (10.14) tecnazene (117-18-0) and (10.15) tolclofos-methyl (57018-04-9). 25 (11) Inhibitors of the melanine biosynthesis, for example (11.1) carpropamid (104030-54-8), (11.2) diclocymet (139920-32-4), (11.3) fenoxanil (115852-48-7), (11.4) phthalide (27355-22-2), (11.5) pyroquilon (57369-32-1), (11.6) tricyclazole (41814-78-2) and (11.7) 2,2,2-trifluoroethyl {3-methyl-1-[(4 m ethylbenzoyl)am ino] butan-2-yl}carbamate (851524-22-6) (W02005042474). 30 (12) Inhibitors of the nucleic acid synthesis, for example (12.1) benalaxyl (71626-11-4), (12.2) benalaxyl M (kiralaxyl) (98243-83-5), (12.3) bupirimate (41483-43-6), (12.4) clozylacon (67932-85-8), (12.5) dimethirimol (5221-53-4), (12.6) ethirimol (23947-60-6), (12.7) furalaxyl (57646-30-7), (12.8) hymexazol (10004-44-1), (12.9) metalaxyl (57837-19-1), (12.10) metalaxyl-M (mefenoxam) (70630-17-0), (12.11) 35 ofurace (58810-48-3), (12.12) oxadixyl (77732-09-3) and (12.13) oxolinic acid (14698-29-4). (13) Inhibitors of the signal transduction, for example (13.1) chlozolinate (84332-86-5), (13.2) fenpiclonil (74738-17-3), (13.3) fludioxonil (131341-86-1), (13.4) iprodione (36734-19-7), (13.5) procymidone (32809-16-8), (13.6) quinoxyfen (124495-18-7) and (13.7) vinclozolin (50471-44-8). 40 WO 2011/151368 25 PCT/EP2011/059024 (14) Compounds capable to act as an uncoupler, like for example (14.1) binapacryl (485-31-4), (14.2) dinocap (131-72-6), (14.3) ferimzone (89269-64-7), (14.4) fluazinam (79622-59-6) and (14.5) meptyldinocap (131-72-6). 5 (15) Further compounds, like for example (15.1) benthiazole (21564-17-0), (15.2) bethoxazin (163269-30 5), (15.3) capsimycin (70694-08-5), (15.4) carvone (99-49-0), (15.5) chinomethionat (2439-01-2), (15.6) pyriofenone (chlazafenone) (688046-61-9), (15.7) cufraneb (11096-18-7), (15.8) cyflufenamid (180409 60-3), (15.9) cymoxanil (57966-95-7), (15.10) cyprosulfamide (221667-31-8), (15.11) dazomet (533-74-4), (15.12) debacarb (62732-91-6), (15.13) dichlorophen (97-23-4), (15.14) diclomezine (62865-36-5), 10 (15.15) difenzoquat (49866-87-7), (15.16) difenzoquat methylsulphate (43222-48-6), (15.17) diphenylamine (122-39-4), (15.18) ecomate, (15.19) fenpyrazamine (473798-59-3), (15.20) flumetover (154025-04-4), (15.21) fluoroimide (41205-21-4), (15.22) flusulfamide (106917-52-6), (15.23) flutianil (304900-25-2), (15.24) fosetyl-aluminium (39148-24-8), (15.25) fosetyl-calcium, (15.26) fosetyl-sodium (39148-16-8), (15.27) hexachlorobenzene (118-74-1), (15.28) irumamycin (81604-73-1), (15.29) 15 methasulfocarb (66952-49-6), (15.30) methyl isothiocyanate (556-61-6), (15.31) metrafenone (220899 03-6), (15.32) mildiomycin (67527-71-3), (15.33) natamycin (7681-93-8), (15.34) nickel dimethyldithiocarbamate (15521-65-0), (15.35) nitrothal-isopropyl (10552-74-6), (15.36) octhilinone (26530-20-1), (15.37) oxamocarb (917242-12-7), (15.38) oxyfenthiin (34407-87-9), (15.39) pentachlorophenol and salts (87-86-5), (15.40) phenothrin, (15.41) phosphorous acid and its salts 20 (13598-36-2), (15.42) propamocarb-fosetylate, (15.43) propanosine-sodiu m (88498-02-6), (15.44) proquinazid (189278-12-4), (15.45) pyrimorph (868390-90-3), (15.46) pyrrolnitrine (1018-71-9) (EP-A 1 559 320), (15.47) tebufloquin (376645-78-2), (15.48) tecloftalam (76280-91-6), (15.49) tolnifanide (304911-98-6), (15.50) triazoxide (72459-58-6), (15.51) trichlamide (70193-21-4), (15.52) zarilamid (84527-51-5), (15.53) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2 25 yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-m ethylpropanoate (517875-34-2) (W02003035617), (15.54) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2 yl}piperid in-1 -yl)-2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]ethanone (1003319-79-6) (WO 2008013622), (15.55) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2 yl}piperid in-1 -yl)-2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]ethanone (1003319-80-9) (WO 30 2008013622), (15.56) 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2 yl}piperid in-1 -yl)-2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]ethanone (1003318-67-9) (WO 2008013622), (15.57) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1 H-imidazole-1-carboxylate (111227-17-9), (15.58) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine (13108-52-6), (15.59) 2,3-dibutyl-6 chlorothieno[2,3-d]pyrimidin-4(3H)-one (221451-58-7), (15.60) 2,6-dimethyl-1 H,5H-[1,4]dithiino[2,3-c:5,6 35 c']dipyrrole-1,3,5,7(2H,6H)-tetrone, (15.61) 2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]-l -(4-{4-[(5R) 5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1 -yl)ethanone (1003316-53-7) (WO 2008013622), (15.62) 2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]-1 -(4-{4-[(5S)-5-phenyl-4,5-dihydro 1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1 -yl)ethanone (1003316-54-8) (WO 2008013622), (15.63) 2-[5 m ethyl-3-(trifluoromethyl)- 1 H-pyrazol- 1-yl]-1 -{4-[4-(5-phenyl-4,5-d i hyd ro- 1,2-oxazol-3-yl)- 1,3-thiazol-2 40 yl]piperidin-1-yl}ethanone (1003316-51-5) (WO 2008013622), (15.64) 2-butoxy-6-iodo-3-propyl-4H chromen-4-one, (15.65) 2-chloro-5-[2-chloro-1 -(2,6-difluoro-4-methoxyphenyl)-4-methyl-1 H-imidazol-5 yl]pyridine, (15.66) 2-phenylphenol and salts (90-43-7), (15.67) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4- WO 2011/151368 26 PCT/EP2011/059024 dihydroisoquinolin-1-yl)quinoline (861647-85-0) (W02005070917), (15.68) 3,4,5-trichloropyridine-2,6 dicarbonitrile (17824-85-0), (15.69) 3-[5-(4-chlorophenyl)-2,3-dimethyl- 1,2-oxazolidin-3-yl]pyridine, (15.70) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (15.71) 4-(4-chlorophenyl)-5-(2,6 difluorophenyl)-3,6-dimethylpyridazine, (15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73) 5-chloro-N' 5 phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide (134-31-6), (15.74) 5-fluoro-2-[(4 fluorobenzyl)oxy]pyrimidin-4-am ine (1174376-11-4) (W02009094442), (15.75) 5-fluoro-2-[(4 methylbenzyl)oxy]pyrimidin-4-amine (1174376-25-0) (W02009094442), (15.76) 5-methyl-6 octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, (15.77) ethyl (2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, (15.78) N'-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N 10 methylimidoformamide, (15.79) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1 yloxy)phenyl]propanamide, (15.80) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1 yloxy)phenyl]propanamide, (15.81) N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3 carboxamide, (15.82) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide, (15.83) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide, (15.84) N-{(E) 15 [(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide (221201 92-9), (15.85) N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2 phenylacetamide (221201-92-9), (15.86) N'-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5 methylphenyl}-N-ethyl-N-methylimidoformamide, (15.87) N-methyl-2-(1 -{[5-methyl-3-(trifluoromethyl)-1 H pyrazol-1 -yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1 -yl)- 1,3-thiazole-4-carboxamide 20 (922514-49-6) (WO 2007014290), (15.88) N-methyl-2-(1 -{[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 yl]acetyl}piperidin-4-yl)-N-[(1 R)-1,2,3,4-tetrahydronaphthalen-1 -yl]-1,3-thiazole-4-carboxamide (922514 07-6) (WO 2007014290), (15.89) N-methyl-2-(1 -{[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide (922514 48-5) (WO 2007014290), (15.90) pentyl {6-[({[(1-methyl-1 H-tetrazol-5 25 yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.91) phenazine-1 -carboxylic acid, (15.92) quinolin-8-ol (134-31-6), (15.93) quinolin-8-ol sulfate (2:1) (134-31-6) and (15.94) tert-butyl {6 [Q[(1 -methyl-1 H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate. (16) Further compounds, like for example (16.1) 1 -methyl-3-(trifluoromethyl)-N-[2' 30 (trifluoromethyl)biphenyl-2-y]-1 H-pyrazole-4-carboxamide, (16.2) N-(4'-chlorobiphenyl-2-yl)-3 (difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxamide, (16.3) N-(2',4'-dichlorobiphenyl-2-yl)-3 (difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxamide, (16.4) 3-(difluoromethyl)-1 -methyl-N-[4' (trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.5) N-(2',5'-difluorobiphenyl-2-yl)-1 -methyl 3-(trifluoromethyl)-1 H-pyrazole-4-carboxamide, (16.6) 3-(difluoromethyl)-1 -methyl-N-[4'-(prop-1 -yn-1 35 yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.7) 5-fluoro-1,3 dimethyl-N-[4'-(prop-1 -yn-1 -yl)biphenyl-2-yl]-1 H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.8) 2-chloro-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide (known from WO 2004/058723), (16.9) 3-(difluoromethyl)-N-[4'-(3,3-dimethylbut-1 -yn-1 -yl)biphenyl-2-yl]-1 -methyl-1 H pyrazole-4-carboxamide (known from WO 2004/058723), (16.10) N-[4'-(3,3-dimethylbut-1-yn-1 40 yl)biphenyl-2-yl]-5-fluoro- 1,3-dimethyl-1 H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.11) 3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.12) N-(4'-ethynylbiphenyl-2-yl)-5-fluoro- 1,3-dimethyl-1 H-pyrazole-4-carboxamide WO 2011/151368 27 PCT/EP2011/059024 (known from WO 2004/058723), (16.13) 2-chloro-N-(4'-ethynylbiphenyl-2-yl)pyridine-3-carboxamide (known from WO 2004/058723), (16.14) 2-chloro-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3 carboxamide (known from WO 2004/058723), (16.15) 4-(difluoromethyl)-2-methyl-N-[4' (trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide (known from WO 2004/058723), (16.16) 5 5 fluoro-N-[4'-(3-hydroxy-3-methylbut-1 -yn-1 -yl)biphenyl-2-yl]-1,3-dimethyl-1 H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.17) 2-chloro-N-[4'-(3-hyd roxy-3-methylbut-1 -yn-1 -yl)biphenyl-2 yl]pyridine-3-carboxamide (known from WO 2004/058723), (16.18) 3-(difluoromethyl)-N-[4'-(3-methoxy-3 methylbut-1 -yn-1 -yl)biphenyl-2-yl]-1 -methyl-1 H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.19) 5-fluoro-N-[4'-(3-methoxy-3-methylbut-1 -yn-1 -yl)biphenyl-2-yl]-1,3-dimethyl-1 H-pyrazole-4 10 carboxamide (known from WO 2004/058723), (16.20) 2-chloro-N-[4'-(3-methoxy-3-methylbut-1-yn-1 yl)biphenyl-2-yl]pyridine-3-carboxamide (known from WO 2004/058723), (16.21) (5-bromo-2-methoxy-4 methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone (known from EP-A 1 559 320) and (16.22) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2 (methylsulfonyl)valinamide (220706-93-4). 15 All named mixing partners of the classes (1) to (16) can, if their functional groups enable this, optionally form salts with suitable bases or acids. The composition according to the invention comprising a mixture of a compound of formula (I) with a 20 bactericide compound can also be particularly advantageous. Examples of suitable bactericide mixing partners can be selected in the following list: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. 25 The compounds of formula (I) and the fungicide composition according to the invention can be used to curatively or preventively control the phytopathogenic fungi of plants or crops. Thus, according to a further aspect of the invention, there is provided a method for curatively or preventively controlling the phytopathogenic fungi of plants or crops characterised in that a compound of formula (I) or a fungicide composition according to the invention is applied to the seed, the plant or to the 30 fruit of the plant or to the soil wherein the plant is growing or wherein it is desired to grow. The method of treatment according to the invention can also be useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment can also be useful to treat roots. The method of treatment according to the invention can also be useful to treat the overground parts of the plant such as trunks, stems or stalks, 35 leaves, flowers and fruit of the concerned plant. According to the invention all plants and plant parts can be treated. By plants is meant all plants and plant populations such as desirable and undesirable wild plants, cultivars and plant varieties (whether or not protectable by plant variety or plant breeder's rights). Cultivars and plant varieties can be plants 40 obtained by conventional propagation and breeding methods which can be assisted or supplemented by one or more biotechnological methods such as by use of double haploids, protoplast fusion, random and directed mutagenesis, molecular or genetic markers or by bioengineering and genetic engineering WO 2011/151368 28 PCT/EP2011/059024 methods. By plant parts is meant all above ground and below ground parts and organs of plants such as shoot, leaf, blossom and root, whereby for example leaves, needles, stems, branches, blossoms, fruiting bodies, fruits and seed as well as roots, corms and rhizomes are listed. Crops and vegetative and generative propagating material, for example cuttings, corms, rhizomes, runners and seeds also belong 5 to plant parts. Among the plants that can be protected by the method according to the invention, mention may be made of major field crops like corn, soybean, cotton, Brassica oilseeds such as Brassica napus (e.g. canola), Brassica rapa, B. juncea (e.g. mustard) and Brassica carinata, rice, wheat, sugarbeet, sugarcane, oats, rye, barley, millet, triticale, flax, vine and various fruits and vegetables of various botanical taxa such as Rosaceae sp. (for 10 instance pip fruit such as apples and pears, but also stone fruit such as apricots, cherries, almonds and peaches, berry fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantings), Rubiaceae sp. (for instance coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges and grapefruit); Solanaceae sp. (for instance tomatoes, 15 potatoes, peppers, eggplant), Liiaceae sp., Compositiae sp. (for instance lettuce, artichoke and chicory including root chicory, endive or common chicory), Umbelliferae sp. (for instance carrot, parsley, celery and celeriac), Cucurbitaceae sp. (for instance cucumber - including pickling cucumber, squash, watermelon, gourds and melons), A//iaceae sp. (for instance onions and leek), Cruciferae sp. (for instance white cabbage, red cabbage, broccoli, cauliflower, brussel sprouts, pak choi, kohlrabi, radish, horseradish, cress, Chinese 20 cabbage), Leguminosae sp. (for instance peanuts, peas and beans beans - such as climbing beans and broad beans), Chenopodiaceae sp. (for instance mangold, spinach beet, spinach, beetroots), Malvaceae (for instance okra), Asparagaceae (for instance asparagus); horticultural and forest crops; ornamental plants; as well as genetically modified homologues of these crops. 25 The method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants of which a heterologous gene has been stably integrated into genome. The expression "heterologous gene" essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other 30 properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology or RNA interference - RNAi - technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event. 35 Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, 40 increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruits, larger plant height, greener leaf WO 2011/151368 29 PCT/EP2011/059024 color, earlier flowering, higher quality and/or a higher nutritional value of the harvested products, higher sugar concentration within the fruits, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected. 5 At certain application rates, the active compound combinations according to the invention may also have a strengthening effect in plants. Accordingly, they are also suitable for mobilizing the defense system of the plant against attack by unwanted microorganisms. This may, if appropriate, be one of the reasons of the enhanced activity of the combinations according to the invention, for example against fungi. Plant strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, 10 those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms. In the present case, unwanted microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Thus, the substances according to the invention can be employed for protecting plants against attack by the 15 abovementioned pathogens within a certain period of time after the treatment. The period of time within which protection is effected generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds. Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether 20 obtained by breeding and/or biotechnological means). Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids. 25 Examples of nematode resistant plants are described in e.g. US Patent Application Nos 11/765,491, 11/765,494, 10/926,819, 10/782,020, 12/032,479, 10/783,417, 10/782,096, 11/657,964, 12/192,904, 11/396,808, 12/166,253, 12/166,239, 12/166,124, 12/166,209, 11/762,886, 12/364,335, 11/763,947, 12/252,453, 12/209,354, 12/491,396 or 12/497,221. Plants and plant cultivars which may also be treated according to the invention are those plants which are 30 resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance. Plants and plant cultivars which may also be treated according to the invention, are those plants 35 characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early 40 flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, WO 2011/151368 30 PCT/EP2011/059024 seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability. 5 Examples of plants with the above-mentioned traits are non-exhaustively listed in Table A. Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses). Such plants are typically made by crossing an inbred 10 male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent). Hybrid seed is typically harvested from the male sterile plants and sold to growers. Male sterile plants can sometimes (e.g. in corn) be produced by detasseling, i.e. the mechanical removal of the male reproductive organs (or males flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome. In that case, and especially when seed is the desired product to be 15 harvested from the hybrid plants it is typically useful to ensure that male fertility in the hybrid plants is fully restored. This can be accomplished by ensuring that the male parents have appropriate fertility restorer genes which are capable of restoring the male fertility in hybrid plants that contain the genetic determinants responsible for male-sterility. Genetic determinants for male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) were for instance described in Brassica species 20 (WO 92/05251, WO 95/09910, WO 98/27806, WO 05/002324, WO 06/021972 and US 6,229,072). However, genetic determinants for male sterility can also be located in the nuclear genome. Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering. A particularly useful means of obtaining male-sterile plants is described in WO 89/10396 in which, for example, a ribonuclease such as barnase is selectively expressed in the tapetum cells in the stamens. Fertility can 25 then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar (e.g. WO 91/02069). Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or 30 more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance. Herbicide-resistant plants are for example glyphosate-tolerant plants, i.e. plants made tolerant to the herbicide glyphosate or salts thereof. Plants can be made tolerant to glyphosate through different means. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding 35 the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the genes encoding a Petunia EPSPS (Shah et al., 1986, Science 233, 478-481), a Tomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289), or an Eleusine EPSPS (WO 40 01/66704). It can also be a mutated EPSPS as described in for example EP 0837944, WO 00/66746, WO 00/66747 or WO02/26995. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxido-reductase enzyme as described in U.S. Patent Nos. 5,776,760 and WO 2011/151368 31 PCT/EP2011/059024 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme as described in for example WO 02/36782, WO 03/092360, WO 05/012515 and WO 07/024782. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described in for example WO 5 01/024615 or WO 03/013226. Plants expressing EPSPS genes that confer glyphosate tolerance are described in e.g. US Patent Application Nos 11/517,991, 10/739,610, 12/139,408, 12/352,532, 11/312,866, 11/315,678, 12/421,292, 11/400,598, 11/651,752, 11/681,285, 11/605,824, 12/468,205, 11/760,570, 11/762,526, 11/769,327, 11/769,255, 11/943801 or 12/362,774. Plants comprising other genes that confer glyphosate tolerance, such as decarboxylase genes, are described in e.g. US patent 10 applications 11/588,811, 11/185,342, 12/364,724, 11/185,560 or 12/423,926. Other herbicide resistant plants are for example plants that are made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate. Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant glutamine synthase enzyme that 15 is resistant to inhibition, e.g. described in US Patent Application No 11/760,602. One such efficient detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinothricin acetyltransferase are for example described in U.S. Patent Nos. 5,561,236; 5,648,477; 5,646,024; 5,273,894; 5,637,489; 5,276,268; 5,739,082; 5,908,810 and 7,112,665. 20 Further herbicide-tolerant plants are also plants that are made tolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD). Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is transformed into homogentisate. Plants tolerant to HPPD-inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated or chimeric HPPD enzyme as described in WO 25 96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387, or US 6,768,044.. Tolerance to HPPD-inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD-inhibitor. Such plants and genes are described in WO 99/34008 and WO 02/36787. Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding an 30 enzyme having prephenate deshydrogenase (PDH) activity in addition to a gene encoding an HPPD tolerant enzyme, as described in WO 2004/024928. Further, plants can be made more tolerant to HPPD inhibitor herbicides by adding into their genome a gene encoding an enzyme capable of metabolizing or degrading HPPD inhibitors, such as the CYP450 enzymes shown in WO 2007/103567 and WO 2008/150473. 35 Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pryimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides. Different mutations in the ALS enzyme (also known as acetohydroxyacid synthase, AHAS) are known to confer tolerance to different herbicides and groups of herbicides, as described for example in Tranel and Wright (2002, Weed 40 Science 50:700-712), but also, in U.S. Patent No. 5,605,011, 5,378,824, 5,141,870, and 5,013,659. The production of sulfonylurea-tolerant plants and imidazolinone-tolerant plants is described in U.S. Patent Nos. 5,605,011; 5,013,659; 5,141,870; 5,767,361; 5,731,180; 5,304,732; 4,761,373; 5,331,107; WO 2011/151368 32 PCT/EP2011/059024 5,928,937; and 5,378,824; and international publication WO 96/33270. Other imidazolinone-tolerant plants are also described in for example WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351, and WO 2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants are also described in for example WO 07/024782 and US 5 Patent Application No 61/288958. Other plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or mutation breeding as described for example for soybeans in U.S. Patent 5,084,082, for rice in WO 97/41218, for sugar beet in U.S. Patent 5,773,702 and WO 99/057965, for lettuce in U.S. Patent 5,198,599, or for sunflower in WO 01/065922. 10 Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance. 15 An "insect-resistant transgenic plant", as used herein, includes any plant containing at least one transgene comprising a coding sequence encoding: 1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins listed by Crickmore et al. (1998, Microbiology and Molecular Biology Reviews, 62: 807-813), updated by Crickmore et al. (2005) at the Bacillus thuringiensis 20 toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/NeilCrickmore/Bt/), or insecticidal portions thereof, e.g., proteins of the Cry protein classes CrylAb, CrylAc, Cry1B, CrylC, CrylD, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof (e.g. EP 1999141 and WO 2007/107302), or such proteins encoded by synthetic genes as e.g. described in and US Patent Application No 25 12/249,016 ; or 2) a crystal protein from Bacillus thuringiensis or a portion thereof which is insecticidal in the presence of a second other crystal protein from Bacillus thuringiensis or a portion thereof, such as the binary toxin made up of the Cry34 and Cry35 crystal proteins (Moellenbeck et al. 2001, Nat. Biotechnol. 19: 668-72; Schnepf et al. 2006, Applied Environm. Microbiol. 71, 1765-1774) or 30 the binary toxin made up of the Cry1A or Cryl F proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Appl. No. 12/214,022 and EP 08010791.5); or 3) a hybrid insecticidal protein comprising parts of different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g., the CrylA.105 protein produced by corn event MON89034 (WO 2007/027777); or 35 4) a protein of any one of 1) to 3) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation, such as the Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A protein in corn event MIR604; or 40 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus, or an insecticidal portion thereof, such as the vegetative insecticidal (VIP) proteins listed at: WO 2011/151368 PCT/EP2011/059024 http://www.lifesci.sussex.ac.uk/home/NeilCrickmore/Bt/vip.html, e.g., proteins from the VIP3Aa protein class; or 6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the 5 binary toxin made up of the VIP1A and VIP2A proteins (WO 94/21795); or 7) a hybrid insecticidal protein comprising parts from different secreted proteins from Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins in 1) above or a hybrid of the proteins in 2) above; or 8) a protein of any one of 5) to 7) above wherein some, particularly 1 to 10, amino acids have 10 been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in cotton event COT1 02; or 9) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the 15 presence of a crystal protein from Bacillus thuringiensis, such as the binary toxin made up of VIP3 and CrylA or Cry1F (US Patent Appl. No. 61/126083 and 61/195019), or the binary toxin made up of the VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Appl. No. 12/214,022 and EP 08010791.5). 10) a protein of 9) above wherein some, particularly 1 to 10, amino acids have been replaced by 20 another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein) Of course, an insect-resistant transgenic plant, as used herein, also includes any plant comprising a 25 combination of genes encoding the proteins of any one of the above classes 1 to 10. In one embodiment, an insect-resistant plant contains more than one transgene encoding a protein of any one of the above classes 1 to 10, to expand the range of target insect species affected when using different proteins directed at different target insect species, or to delay insect resistance development to the plants by using different proteins insecticidal to the same target insect species but having a different mode of action, such 30 as binding to different receptor binding sites in the insect. An "insect-resistant transgenic plant", as used herein, further includes any plant containing at least one transgene comprising a sequence producing upon expression a double-stranded RNA which upon ingestion by a plant insect pest inhibits the growth of this insect pest, as described e.g. in WO 35 2007/080126, WO 2006/129204, WO 2007/074405, WO 2007/080127 and WO 2007/035650. Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress 40 resistance. Particularly useful stress tolerance plants include: WO 2011/151368 PCT/EP2011/059024 1) plants which contain a transgene capable of reducing the expression and/or the activity of poly(ADP-ribose) polymerase (PARP) gene in the plant cells or plants as described in WO 00/04173, WO/2006/045633, EP 04077984.5, or EP 06009836.5. 2) plants which contain a stress tolerance enhancing transgene capable of reducing the 5 expression and/or the activity of the PARG encoding genes of the plants or plants cells, as described e.g. in WO 2004/090140. 3) plants which contain a stress tolerance enhancing transgene coding for a plant-functional enzyme of the nicotineamide adenine dinucleotide salvage synthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyl 10 transferase, nicotinamide adenine dinucleotide synthetase or nicotine amide phosphorybosyltransferase as described e.g. in EP 04077624.7, WO 2006/133827, PCT/EP07/002433, EP 1999263, or WO 2007/107326. Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which 15 may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product such as 1) transgenic plants which synthesize a modified starch, which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the 20 gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications. Said transgenic plants synthesizing a modified starch are disclosed, for example, in EP 0571427, WO 95/04826, EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/11188, WO 97/26362, WO 97/32985, WO 97/42328, WO 25 97/44472, WO 97/45545, WO 98/27212, WO 98/40503, Wa99/58688, WO 99/58690, WO 99/58654, WO 00/08184, WO 00/08185, WO 00/08175, WO 00/28052, WO 00/77229, WO 01/12782, WO 01/12826, WO 02/101059, WO 03/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, 30 WO 00/22140, WO 2006/063862, WO 2006/072603, WO 02/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 01/14569, WO 02/79410, WO 03/33540, WO 2004/078983, WO 01/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950, WO 99/66050, WO 99/53072, US 6,734,341, WO 00/11192, WO 98/22604, WO 98/32326, WO 01/98509, WO 01/98509, WO 2005/002359, US 5,824,790, US 6,013,861, WO 35 94/04693, WO 94/09144, WO 94/11520, WO 95/35026, WO 97/20936 2) transgenic plants which synthesize non starch carbohydrate polymers or which synthesize non starch carbohydrate polymers with altered properties in comparison to wild type plants without genetic modification. Examples are plants producing polyfructose, especially of the inulin and levan-type, as disclosed in EP 0663956, WO 96/01904, WO 96/21023, WO 98/39460, and WO 40 99/24593, plants producing alpha-1,4-glucans as disclosed in WO 95/31553, US 2002031826, US 6,284,479, US 5,712,107, WO 97/47806, WO 97/47807, WO 97/47808 and WO 00/14249, plants producing alpha-1,6 branched alpha- 1,4-glucans, as disclosed in WO 00/73422, plants WO 2011/151368 35 PCT/EP2011/059024 producing alternan, as disclosed in e.g. WO 00/47727, WO 00/73422, EP 06077301.7, US 5,908,975 and EP 0728213, 3) transgenic plants which produce hyaluronan, as for example disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006304779, and WO 2005/012529. 5 4) transgenic plants or hybrid plants, such as onions with characteristics such as 'high soluble solids content', 'low pungency' (LP) and/or 'long storage' (LS), as described in US Patent Appl. No. 12/020,360 and 61/054,026. Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic 10 engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics and include: a) Plants, such as cotton plants, containing an altered form of cellulose synthase genes as described in WO 98/00549 15 b) Plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids as described in WO 2004/053219 c) Plants, such as cotton plants, with increased expression of sucrose phosphate synthase as described in WO 01/17333 d) Plants, such as cotton plants, with increased expression of sucrose synthase as described in 20 WO 02/45485 e) Plants, such as cotton plants, wherein the timing of the plasmodesmatal gating at the basis of the fiber cell is altered, e.g. through downregulation of fiber-selective p-1,3-glucanase as described in WO 2005/017157, or as described in EP 08075514.3 or US Patent Appl. No. 61/128,938 25 f) Plants, such as cotton plants, having fibers with altered reactivity, e.g. through the expression of N-acetylglucosaminetransferase gene including nodC and chitin synthase genes as described in WO 2006/136351 Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic 30 engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics and include: a) Plants, such as oilseed rape plants, producing oil having a high oleic acid content as 35 described e.g. in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947 b) Plants such as oilseed rape plants, producing oil having a low linolenic acid content as described in US 6,270,828, US 6,169,190, or US 5,965,755 c) Plant such as oilseed rape plants, producing oil having a low level of saturated fatty acids as described e.g. in US Patent No. 5,434,283 or US Patent Application No 12/668303 40 Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or WO 2011/151368 36 PCT/EP2011/059024 related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering as described in US Patent Appl. No. 61/135,230 W009/068313 and WO10/006732. 5 Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or combination of transformation events, that are the subject of petitions for non regulated status, in the United States of America, to the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) whether such petitions are granted or are still pending. At any time this information is readily available from APHIS (4700 River Road Riverdale, MD 10 20737, USA), for instance on its internet site (URL http://www.aphis.usda.gov/brs/notreg.html). On the filing date of this application the petitions for nonregulated status that were pending with APHIS or granted by APHIS were those listed in table B which contains the following information: - Petition : the identification number of the petition. Technical descriptions of the transformation 15 events can be found in the individual petition documents which are obtainable from APHIS, for example on the APHIS website, by reference to this petition number. These descriptions are herein incorporated by reference. - Extension of Petition : reference to a previous petition for which an extension is requested. - Institution : the name of the entity submitting the petition. 20 - Regulated article : the plant species concerned. - Transgenic phenotype : the trait conferred to the plants by the transformation event. - Transformation event or line : the name of the event or events (sometimes also designated as lines or lines) for which nonregulated status is requested. - APHIS documents : various documents published by APHIS in relation to the Petition and 25 which can be requested with APHIS. Additional particularly useful plants containing single transformation events or combinations of transformation events are listed for example in the databases from various national or regional regulatory agencies (see for example http://gmoinfo.jrc.it/gmpbrowse.aspx and http://www.agbios.com/dbase.php). 30 Further particularly transgenic plants include plants containing a transgene in an agronomically neutral or beneficial position as described in any of the patent publications listed in Table C. Table A 35 Trait Reference Water use efficiency WO 2000/073475 Nitrogen use efficiency WO 1995/009911 WO 2007/076115 WO 1997/030163 WO 2005/103270 WO 2007/092704 WO 2002/002776 Improved photosynthesis WO 2008/056915 WO 2004/101751 WO 2011/151368 37 PCT/EP2011/059024 Nematode resistance WO 1995/020669 WO 2003/033651 WO 2001/051627 WO 1999/060141 WO 2008/139334 WO 1998/012335 WO 2008/095972 WO 1996/030517 WO 2006/085966 WO 1993/018170 Reduced pod dehiscence WO 2006/009649 WO 1997/013865 WO 2004/113542 WO 1996/030529 WO 1999/015680 WO 1994/023043 WO 1999/000502 Aphid resistance WO 2006/125065 WO 2008/067043 WO 1997/046080 WO 2004/072109 Sclerotinia resistance WO 2006/135717 WO 2005/000007 WO 2006/055851 WO 2002/099385 WO 2005/090578 WO 2002/061043 Botrytis resistance WO 2006/046861 WO 2002/085105 Bremia resistance US 20070022496 WO 2004/049786 WO 2000/063432 Erwinia resistance WO 2004/049786 Closterovirus resistance WO 2007/073167 WO 2002/022836 WO 2007/053015 Stress tolerance (including WO 2010/019838 W02008/002480 drought tolerance) WO 2009/049110 W02005/033318 Tobamovirus resistance WO 2006/038794 Table B Petitions of Nonregulated Status Granted or Pending by APHIS as of March 31, 2010 NOTE: To obtain the most up-to-date list of Crops No Longer Regulated, please look at the Current Status of Petitions. This list is automatically updated and reflects all petitions received to date by APHIS, including petitions pending, withdrawn, or approved. Abbreviations: CMV-cucumber mosaic virus; CPB-colorado potato beetle; PLRV- potato leafroll virus; PRSV-papaya ringspot virus; PVY-potato virus Y; WMV2- watermelon mosaic virus 2 ZYMV-zucchini yellow mosaic virus 5 WO 2011/151368 38 PCT/EP2011/059024 Petitions for Nonregulated Status Pending 10-070- Virginia Tech Peanut Sclerotinia blight N70, P39, and 01 p __________resistant W171 -349- ____ AgroSciences Soybean Herbicide Tolerant DAS-68416-4 -328- _____ Science Soybean Herbicide Tolerant FG72 09-233- Dow Corn Herbicide Tolerant DAS-40278-9 09-201- Monsanto Soybean MON-87705-6 09-183- Monsanto Soybean MON-87769 09-082- Monsanto Soybean Lepidopteran resistant MON 87701 09-063- Stine Seed Corn Glyphosate tolerant HCEM485 09-055- Monsanto Corn Drought Tolerant MON 87460 09-015- BASE Plant BPS-CV1 27-9 01p ______Science, LLC Soybean Herbicide Tolerant Soybean 08-366- ArborGen Eucalyptu Freeze Tolerant, ARB-FTE1-08 01 p ______s Fertility Altered _______ 08-340- Bayer Cotton Glufosinate Tolerant', 3440GB1 01 p __________Insect Resistant T34OXH19 Male Sterile, Fertility 08-338- Pioneer Corn Restored, Visual DP-32138-1 01 p ~~~Marker________ 0-15- Florigene Rose Altered Flower Color and590 0-253- Syngenta Corn Lepidopteran resistant MIR-162 Maize 0-108- Syngenta Cotton Lepidopteran Resistant COT67B 06-354- Pioneer Soybean High Oleic Acid DP-305423-1 0-280- Syngenta Corn Thermostable alpha- 3272 0l -110-_ Fonae Genetics Alfalfa Glyphosate Tolerant J101, J163 0l -104- ___ Scott & bentgrass Glyphosate Tolerant ASR368 WO 2011/151368 39 PCT/EP2011/059024 Petitions for Nonregulated Status Grante 07-152- Pine on glyphosate & 01 p PioneerCorn Imidazolinone tolerant DP-098140-6 04-337- University of Paaa Papaya Ringspot Virus X17-2 01p ______Florida Resistant________ -332- ___ _ Cop cience Cotton Glyphosate tolerant GHB614 06-298- Monsanto Corn European Corn Borer MON 89034 01 p __________resistant________ 06-271- ~Glyphosate & 364 01- Pioneer Soybean acetolntctate synthase DO 356043-5) 06-234- 9839Op Bayer Rie Phosphinothricin LRCEO 01p 98-329-01p_ CropScience Rice___tolerant LLRICE601___ 0-178- Monsanto Soybean Glyphosate tolerant MON 89788 04-362- SnetCon Corn Rootworm MR0 01p ynetCon Protected MR0 04-264- AR lm Plum Pox Virus C 01 p ARS____ Plum___Resistant C5_______ -229- Monsanto Corn High Lysine LY038 04-125- Monsanto Corn Corn Rootworm 88017 01 p __________Resistant________ 0-086- Monsanto Cotton Glyphosate Tolerant MON 88913 03-353- Do on Corn Rootworm592 01 p Dow____ Corn___Resistant 59122 _____ -323 pMonsanto__Sugar Glyphosate Tolerant H7-1 03-181-Lepidopteran Resistant 03181-00-136-01p Dow Corn & Phosphinothricin TC-6275 01 p ~~~tolerant________ 0-155- Syngenta Cotton Lepidopteran Resistant COT 102 0-036- Mycogen/Dow Cotton Lepidopteran Resistant 281-24-236 0-036- Mycogen/Dow Cotton Lepidopteran Resistant 3006-210-23 02-042- Aventis Cotton Phosphinothericin LLCotton25 01 p __________tolerant________ 0-324- 98-216-01p Monsanto RapeseeGlpoaetern RT0 Phosphinothricin 0-206- 9-7-1 AvniRapesee tolerant & pollination MS1 & RF1/RF2 01 p 98-278-lp Aventis dcontrol________ 0-206- 97-205-01p Aventis Rapesee Phosphinothriciri Topas 19/2 0 2 p... ... __ _ _ ... _ _ _ _ _ _ d to le ra n t _ _ _ _ _ _ _ _ _ _ _ _ _ _ __.............................................................
    WO 2011/151368 40 PCT/EP2011/059024 01-137- Monsanto Corn Corn Rootworm MON 863 01p Resistant 01-121- Vector Tobacco Reduced nicotine Vector 21-41 00-342- Monsanto Cotton Lepidopteran resistant Cotton Event 01 p __ _ _ _ __ _ _ _ _ _ _ _ _ _ _ _ _ 15985 00-136- Mycogen d/o Lepidopteran resistant 01 now&ioneer Corn phosphinothricin Line 1507 01p Dow & Pioneer tolerant _______ 0-011- 97-099-01p Monsanto Corn Glyphosate tolerant NK603 99-173- 9 7
    -
    2 0 4 -01p Monsanto Potato PLRV & CPB resistant RBMT22-82 Phosphinothricin 8-349- 95- 22 8-01p AgrEvo Corn tolerant and Male MS6 sterile 98-335- U. of Tolerant to soil 01p Saskatchewan Flax residues of sulfonyl CDC Triffid urea herbicide 98-329- Phosphinothricin LLRICE06, 01p AgrEvo Rice tolerant LLRICE62 Phosphinothricin 98-278- AgrEvo Rapesee tolerant & Pollination MS8 & RF3 01 p d control 98-238- AgrEvo Soybean Phosphinothricin GU262 01p tolerant 98-216- Monsanto Rapesee Glyphosate tolerant RT73 01 p ______d Gyhst oeat R7 98-173- Novartis Seeds & Beet Glyphosate tolerant GTSB77 Olp ______Monsanto _____________ _______ 98-014- 96-068-01p AgrEvo Soybean Phosphinothricin A5547-127 Olp 906Ol ArvoSyentolerant _______ Male sterile & -342- Pioneer Corn Phosphinothricin 676, 678, 680 tolerant RBMT15-101, 9-3 Monsanto Potato CPB & PVY resistant SEMT15-02, 01p SEMT15-15 97-336- AgrEvo Beet Phosphinothricin T-120-7 01p tolerant 97-287- Monsanto Tomato Lepidopteran resistant 5345 97-265- Phosphinothricin 6p AgrEvo Corn tolerant & Lep. CBH-351 resistant 97-205- AgrEvo Rapesee Phosphinothricin T45 01 p ______d tolerantT4 -204- Monsanto Potato CPB & PLRV resistant RBMT21-9 & 97-148- Bejo Cichoriu Male sterile RM3-3, RM3-4, 01p m intybus RM3-6 97-099- Monsanto Corn Glyphosate tolerant GA21 97-013- Bromoxynil tolerant & Events 31807 & 01p CalgeneICotton Lepidopteran resistant 31808 WO 2011/151368 41 PCT/EP2011/059024 97-008- Du Pont Soybean Oil profile altered G94-1, G94-19, G 01 p __ _ _ _ __ _ _ _ _ _ _ _ _ _ _ _ _ 168 96-317- Monsanto Corn Glyphosate tolerant & MON802 01 p _____ ___ECB resistant ______ 96-291- DeKalb Corn European Corn Borer DBT418 01p resistant 1-248- 92-196-01p Calgene Tomato Fruit ripening altered FLAVSAVR line W62, W98, A2704 96-068- AgrEvo Soybean Phosphinothricin 12, A2704-21, 01 p tolerant A5547-35 96-051- Cornell U Papaya PRSV resistant 55-1, 63-1 96-017- European Corn Borer MON809 & 01p 95-001p 1p Monsanto Corn resistant MON810 95-352- Asgrow Squash CMV, ZYMV, WMV2 CZW-3 01p resistant SBT02-5 & -7, 95-338- Monsanto Potato CPB resistant ATBT04-6 &-27, 30, -31, -36 95-324- Agritope Tomato Fruit ripening altered 35 1 N 95-256- Du Pont Cotton Sulfonylurea tolerant 19-51a 95-228- Plant Genetic Corn Male sterile MS3 Olp ______SystemsCon MlstreM3 95-195- Northrup King Corn European Corn Borer Bt11 01p resistant 95-179- 92-196-01p Calgene Tomato Fruit ripening altered FLASA R lines 95-145- DeKalb Corn Phosphinothricin B16 01p tolerant 95-093- Monsanto Corn Lepidopteran resistant MON 80100 95-053- Monsanto Tomato Fruit ripening altered 8338 95-045- Monsanto Cotton Glyphosate tolerant 1445, 1698 95-030- 92-196-01p Calgene Tomato Fruit ripening altered FLAdRAVI lines 94-357- AgrEvo Corn Phosphinothricin T14, T25 01p tolerant 94-319- Ciba Seeds Corn Lepidopteran resistant Event 176 94-308- Monsanto Cotton Lepidopteran resistant 531, 757, 1076 94-290- Zeneca & Tomato Fruit polygalacturonase B, Da, F 01p Petoseed level decreased BT6, BT10, BT12, 94-257 Monsanto Potato Coleopteran resistant BT16, BT17, BT18, 01 p BT23 -230- 92-196-01p Calgene Tomato Fruit ripening altered 9FLARSAR lines 94-228- DNA Plant Tech Tomato Fruit ripening altered 1345-4 94-227- 92-196-01p Calgene Tomato Fruit ripening altered Line N73 1436-111 WO 2011/151368 42 PCT/EP2011/059024 01p 94-090- Calgene Rapesee Oil profile altered pCGN3828 01p d 212/86- 18 & 23 93-258- Monsanto Soybean Glyphosate tolerant 40-3-2 01 p 1__ _ _ _ _ _ _ _ _ _ __ _ _ _ _ _ _ _ _ _ _ _ -196- Calgene Cotton Bromoxynil tolerant BXN 92-204- Upjohn Squash WMV2 & ZYMV ZW-20 01 p __________resistantZW2 92-196- Calgene Tomato Fruit ripening altered FLAVR SAVR *** Extension of Petition Number: Under 7CFR 340.6(e) a person may request that APHIS extend a determination of non-regulated status to other organisms based on their similarity of the previously deregulated article. This column lists the previously granted petition of that degregulated article. **** Preliminary EA: The Environmental Assessment initially available for Public comment prior to finalization. Table C Plant species Event Trait Patent reference Corn PV-ZMGT32 (NK603) Glyphosate tolerance US 2007-056056 Corn MIR604 Insect resistance (Cry3aO55) EP 1 737 290 Corn LY038 High lysine content US 7,157,281 Corn 3272 Self processing corn (alpha- US 2006-230473 amylase) Corn PV-ZMIR13 Insect resistance (Cry3Bb) US 2006-095986 (MON863) Corn DAS-59122-7 Insect resistance US 2006-070139 (Cry34Ab1/Cry35Ab1) Corn TC1507 Insect resistance (Cry1F) US 7,435,807 Corn MON810 Insect resistance (CrylAb) US 2004-180373 Corn VIP1034 Insect resistance WO 03/052073 Corn B16 Glufosinate resistance US 2003-126634 Corn GA21 Glyphosate resistance US 6,040,497 Corn GG25 Glyphosate resistance US 6,040,497 Corn GJ11 Glyphosate resistance US 6,040,497 Corn El 17 Glyphosate resistance US 6,040,497 Corn GAT-ZM1 Glufosinate tolerance WO 01/51654 Corn MON87460 Drought tolerance WO 2009/111263 Corn DP-098140-6 Glyphosate tolerance / ALS WO 2008/112019 inhibitor tolerance Wheat Event 1 Fusarium resistance CA 2561992 (trichothecene 3-0- WO 2011/151368 PCT/EP2011/059024 acetyltransferase) Sugar beet T227-1 Glyphosate tolerance US 2004-117870 Sugar beet H7-1 Glyphosate tolerance WO 2004-074492 Soybean MON89788 Glyphosate tolerance US 2006-282915 Soybean A2704-12 Glufosinate tolerance WO 2006/108674 Soybean A5547-35 Glufosinate tolerance WO 2006/108675 Soybean DP-305423-1 High oleic acid / ALS inhibitor WO 2008/054747 tolerance Rice GAT-OS2 Glufosinate tolerance WO 01/83818 Rice GAT-OS3 Glufosinate tolerance US 2008-289060 Rice PE-7 Insect resistance (CrylAc) WO 2008/114282 Oilseed rape MS-B2 Male sterility WO 01/31042 Oilseed rape MS-BN1/RF-BN1 Male sterility/restoration WO 01/41558 Oilseed rape RT73 Glyphosate resistance WO 02/36831 Cotton CE43-67B Insect resistance (CrylAb) WO 2006/128573 Cotton CE46-02A Insect resistance (CrylAb) WO 2006/128572 Cotton CE44-69D Insect resistance (CrylAb) WO 2006/128571 Cotton 1143-14A Insect resistance (CrylAb) WO 2006/128569 Cotton 1143-51B Insect resistance (CrylAb) WO 2006/128570 Cotton T342-142 Insect resistance (CrylAb) WO 2006/128568 Cotton event3006-210-23 Insect resistance (CrylAc) WO 2005/103266 Cotton PV-GHGT07 (1445) Glyphosate tolerance US 2004-148666 Cotton MON88913 Glyphosate tolerance WO 2004/072235 Cotton EE-GH3 Glyphosate tolerance WO 2007/017186 Cotton T304-40 Insect-resistance (CrylAb) W02008/122406 Cotton Cot202 Insect resistance (VIP3) US 2007-067868 Cotton LLcotton25 Glufosinate resistance WO 2007/017186 Cotton EE-GH5 Insect resistance (CrylAb) WO 2008/122406 Cotton event 281-24-236 Insect resistance (Cry1F) WO 2005/103266 Cotton Cot102 Insect resistance (Vip3A) US 2006-130175 Cotton MON 15985 Insect resistance (Cry1A/Cry2Ab) US 2004-250317 Bent Grass Asr-368 Glyphosate tolerance US 2006-162007 Brinjal EE-1 Insect resistance (CrylAc) WO 2007/091277 Among the diseases of plants or crops that can be controlled by the method according to the invention, mention can be made of: 5 Powdery mildew diseases such as: Blumeria diseases, caused for example by Blumeria graminis; Podosphaera diseases, caused for example by Podosphaera leucotricha; Sphaerotheca diseases, caused for example by Sphaerotheca fuliginea; Uncinula diseases, caused for example by Uncinula necator; WO 2011/151368 PCT/EP2011/059024 Rust diseases such as: Gymnosporangium diseases, caused for example by Gymnosporangium sabinae; Hemileia diseases, caused for example by Hemileia vastatrix; Phakopsora diseases, caused for example by Phakopsora pachyrhizi or Phakopsora 5 meibomiae; Puccinia diseases, caused for example by Puccinia recondite, Puccinia graminis or Puccinia strilformis; Uromyces diseases, caused for example by Uromyces appendiculatus; Oomycete diseases such as: 10 Albugo diseases caused for example by Albugo candida; Bremia diseases, caused for example by Bremia lactucae; Peronospora diseases, caused for example by Peronospora pisi or P. brassicae; Phytophthora diseases, caused for example by Phytophthora infestans; Plasmopara diseases, caused for example by Plasmopara viticola; 15 Pseudoperonospora diseases, caused for example by Pseudoperonospora humulior Pseudoperonospora cubensis; Pythium diseases, caused for example by Pythium ultimum; Leafspot, leaf blotch and leaf blight diseases such as: Alternaria diseases, caused for example by Alternaria solani; 20 Cercospora diseases, caused for example by Cercospora beticola; Cladiosporum diseases, caused for example by Cladiosporium cucumerinum; Cochliobolus diseases, caused for example by Cochliobolus sativus (Conidiaform: Drechslera, Syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum diseases, caused for example by Colletotrichum lindemuthanium; 25 Cycloconium diseases, caused for example by Cycloconium oleaginum; Diaporthe diseases, caused for example by Diaporthe citri; Elsinoe diseases, caused for example by Elsinoe fawcettii; Gloeosporium diseases, caused for example by Gloeosporium laeticolor; Glomerella diseases, caused for example by Glomerella cingulata; 30 Guignardia diseases, caused for example by Guignardia bidwe//i ; Leptosphaeria diseases, caused for example by Leptosphaeria maculans ; Leptosphaeria nodorum; Magnaporthe diseases, caused for example by Magnaporthe grisea; Mycosphaerella diseases, caused for example by Mycosphaerella graminicola ; Mycosphaerella arachidicola; Mycosphaerella fiiensis; 35 Phaeosphaeria diseases, caused for example by Phaeosphaeria nodorum; Pyrenophora diseases, caused for example by Pyrenophora teres, or Pyrenophora tritici repentis; Ramularia diseases, caused for example by Ramularia collo-cygni , or Ramularia areola; Rhynchosporium diseases, caused for example by Rhynchosporium secalis; 40 Septoria diseases, caused for example by Septoria api or Septoria lycopercisi; Typhula diseases, caused for example by Typhula incarnata; Venturia diseases, caused for example by Venturia inaequalis; WO 2011/151368 45 PCT/EP2011/059024 Root, Sheath and stem diseases such as : Corticium diseases, caused for example by Corticium graminearum; Fusarium diseases, caused for example by Fusarium oxysporum; Gaeumannomyces diseases, caused for example by Gaeumannomyces graminis; 5 Rhizoctonia diseases, caused for example by Rhizoctonia solani; Sarocladium diseases caused for example by Sarocladium oryzae; Sclerotium diseases caused for example by Sclerotium oryzae; Tapesia diseases, caused for example by Tapesia acuformis; Thielaviopsis diseases, caused for example by Thielaviopsis basicola; 10 Ear and panicle diseases such as : Alternaria diseases, caused for example by Alternaria spp.; Aspergillus diseases, caused for example by Aspergillus flavus; Cladosporium diseases, caused for example by Cladosporium spp.; Claviceps diseases, caused for example by Claviceps purpurea ; 15 Fusarium diseases, caused for example by Fusarium culmorum; Gibberella diseases, caused for example by Gibberella zeae; Monographella diseases, caused for example by Monographella nivalis; Smut and bunt diseases such as : Sphacelotheca diseases, caused for example by Sphacelotheca reiliana; 20 Tilletia diseases, caused for example by Tilletia caries; Urocystis diseases, caused for example by Urocystis occulta; Ustilago diseases, caused for example by Ustilago nuda; Fruit rot and mould diseases such as : Aspergillus diseases, caused for example by Aspergillus flavus; 25 Botrytis diseases, caused for example by Botrytis cinerea ; Penicillium diseases, caused for example by Penicillium expansum; Rhizopus diseases caused by example by Rhizopus stolonifer Sclerotinia diseases, caused for example by Sclerotinia sclerotiorum; Verticilium diseases, caused for example by Verticilium alboatrum; 30 Seed and soilborne decay, mould, wilt, rot and damping-off diseases : Alternaria diseases, caused for example by Alternaria brassicicola Aphanomyces diseases, caused for example by Aphanomyces euteiches Ascochyta diseases, caused for example by Ascochyta lentis Aspergillus diseases, caused for example by Aspergillus flavus 35 Cladosporium diseases, caused for example by Cladosporium herbarum Cochliobolus diseases, caused for example by Cochliobolus sativus (Conid iaform: Drechslera, Bipolaris Syn: He/minthosporium); Colletotrichum diseases, caused for example by Colletotrichum coccodes; Fusarium diseases, caused for example by Fusarium culmorum; 40 Gibberella diseases, caused for example by Gibberella zeae; Macrophomina diseases, caused for example by Macrophomina phaseolina Monographella diseases, caused for example by Monographella nivalis; WO 2011/151368 46 PCT/EP2011/059024 Penicillium diseases, caused for example by Penicillium expansum Phoma diseases, caused for example by Phoma lingam Phomopsis diseases, caused for example by Phomopsis sojae; Phytophthora diseases, caused for example by Phytophthora cactorum; 5 Pyrenophora diseases, caused for example by Pyrenophora graminea Pyricularia diseases, caused for example by Pyricularia oryzae; Pythium diseases, caused for example by Pythium ultimum; Rhizoctonia diseases, caused for example by Rhizoctonia solani; Rhizopus diseases, caused for example by Rhizopus oryzae 10 Sclerotium diseases, caused for example by Sclerotium rolfsii; Septoria diseases, caused for example by Septoria nodorum; Typhula diseases, caused for example by Typhula incarnata; Verticillium diseases, caused for example by Verticillium dahliae; Canker, broom and dieback diseases such as: 15 Nectria diseases, caused for example by Nectria galligena; Blight diseases such as : Monilinia diseases, caused for example by Moni/inia laxa; Leaf blister or leaf curl diseases such as : Exobasidium diseases caused for example by Exobasidium vexans 20 Taphrina diseases, caused for example by Taphrina deformans; Decline diseases of wooden plants such as: Esca diseases, caused for example by Phaemoniella clamydospora; Eutypa dyeback, caused for example by Eutypa lata; Ganoderma diseases caused for example by Ganoderma boninense; 25 Rigidoporus diseases caused for example by Rigidoporus lignosus Diseases of Flowers and Seeds such as Botrytis diseases caused for example by Botrytis cinerea; Diseases of Tubers such as Rhizoctonia diseases caused for example by Rhizoctonia solani; 30 Helminthosporium diseases caused for example by Helminthosporium solani; Club root diseases such as Plasmodiophora diseases, cause for example by Plamodiophora brassicae. Diseases caused by Bacterial Organisms such as Xanthomonas species for example Xanthomonas campestris pv. oryzae; 35 Pseudomonas species for example Pseudomonas syringae pv. lachrymans; Erwinia species for example Erwinia amylovora. The composition according to the invention may also be used against fungal diseases liable to grow on or inside timber. The term "timber" means all types of species of wood, and all types of working of this wood 40 intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting one or more WO 2011/151368 PCT/EP2011/059024 compounds according to the invention or a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means. The dose of active compound usually applied in the method of treatment according to the invention is 5 generally and advantageously from 10 to 800 g/ha, preferably from 50 to 300 g/ha for applications in foliar treatment. The dose of active substance applied is generally and advantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed in the case of seed treatment. It is clearly understood that the doses indicated herein are given as illustrative examples of the method according to the invention. A person skilled in the art will know how to adapt the application doses, 10 notably according to the nature of the plant or crop to be treated. The compounds or mixtures according to the invention can also be used for the preparation of composition useful to curatively or preventively treat human or animal fungal diseases such as, for example, mycoses, dermatoses, trichophyton diseases and candidiases or diseases caused by 15 Aspergillus spp., for example Aspergillus fumigatus. The various aspects of the invention will now be illustrated with reference to the following table of compound examples and the following preparation or efficacy examples. 20 Table 1 illustrates in a non-limiting manner examples of compounds of formula (I) according to the invention: Z ,Z 4 7 B Si N A z 1 z 2 z 5 z6T Z Z2 Z T (I) In table 1, unless otherwise specified, M+H (Apcl+) means the molecular ion peak plus 1 a.m.u. (atomic mass unit) as observed in mass spectroscopy via positive atmospheric pressure chemical ionisation. 25 In table 1, the logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a reversed-phase column (C 18), using the method described below: Temperature: 40'C ; Mobile phases : 0.1% aqueous formic acid and acetonitrile ; linear gradient from 10% 30 acetonitrile to 90% acetonitrile. Calibration was carried out using unbranched alkan-2-ones (comprising 3 to 16 carbon atoms) with known logP values (determination of the logP values by the retention times using linear interpolation between two successive alkanones). lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals. 35 WO 2011/151368 PCT/EP2011/059024 48 , CN 000 N (o + 'TLOC0 LO C0 NN c o oco co 2 zo 0) 04 cr co 1-C NII N C: ) C) C) C) C) C0 0 0 0 0 z zz z z z eidwexj CI -) WO 2011/151368 PCT/EP2O1 1/059024 49 -Y CY.J 0cy*) cy*) c~)CIS -51 - -51 o: C ~: C: C:) 00 0 00 ta a a a a N Co) N C:) C) C) C) C) C) I-0 0 0 UO CO) - z U- U Z/ z ajdwex~j 00
    C-
    WO 2011/151368 PCT/EP2O1 1/059024 50 cu)* E 'IT C) CN CN co +CN 0. mOC Co) CO )00.000 0) 0 -9L6ci ci i a ,0 0 0 041 041 04 x x a) a) N0 0 T -T o co T-T - -T LO T -T -T Nta) a) a) a) a) N CY) a ,a ,a N 041 N N I-0 0 0 0 0 z z z z 0z z - 041 CY) L ajdwex~ - - -- WO 2011/151368 PCT/EP2O1 1/059024 51 co + mm0 co* co* co* co* 0- CY)CY) ) CY) 0) r- - C0C o: : C: C: C 0 0 0 0 0 0 0 0 0 co T- T- T- T N CO) N C:) 0) C) C) C) C) I-CO 0 0 0 0
    U
    zz z z zz z Zz 00 N- C) ajdwex~j 04-- WO 2011/151368 PCT/EP2O1 1/059024 52 co + NLO m c~) m* co* co* 041 041 0 CY) m-C LO) r o: C: C:) C: 0 0 0 0 0 0 0 0 0 0 0 co T-T - -T NO a- a- T- T N N I I I I 0Y ) a) a) a) a) N 04 )0 0 )0 N N I-0 0 0 0 0
    U
    z Szz - 041 CY) LOU' ajdwex~j0 40 40 WO 2011/151368 PCT/EP2O1 1/059024 53 co + 00mCO co* co* co* co* co* 0o 00) 00 C) 0 0 0 0 0 0 0 0 0 co T- T- T- T LO a- a- a- a N N I I I I C0 ) a) a) a) a) N 041 N N I-0 0 0 0 0 zz z Z/zo z 0 z C0 0- C) ajdwex~j 04I 04J 040 CY) WO 2011/151368 PCT/EP2O1 1/059024 54 (u) +E LfLO. 0.o +o LO C - CY) C.1 aa2 2 2 o a - ci i 0 0 0.1 01 T-.-1T o ao a- T- T-T N LO T -T -T N CY) a) a) a) a) a) N 041 N N I-0 0 0 0 0 /z z z zl
    U
    ajdwex~jC)C)CY Y Y WO 2011/151368 PCT/EP2O1 1/059024 55 co + CN. LO) co* 00 C C0 0) ) 0) ) ) 0) 2 2 2 2 2 01 01 01 0 01 oo o- 0-T N NIa 040 0: ) C) C) C) C) C)0 0O 0 0 0 I-.0 l) 0 0 0 ajdwe~j C) CY)CY) Y)U- WO 2011/151368 PCT/EP2O1 1/059024 56 co + co C 'I LO) 0- 00 C) 0) C) ) 0') 2 2 2 2 2 LQ LQ 0- 0a a0a o LO T -T -T N 04 )0 0 )0 N N I-0 0 0 0 0 zz z~ z - 041 CY) L ajdwex~jNtN WO 2011/151368 PCT/EP2O1 1/059024 57 co + CN CN co* 0- 000 0)04 ) 0Y)0)) 2 2 2 2 2 LQ LQ LQ LQ LQ oo T- a-T N N a)a a a a oY) )a a) a) 0 0 0 0 0 C. 000 0C0 ajdwe~j NtNt
    U'
    WO 2011/151368 PCT/EP2O1 1/059024 58 uu) N C0 C)N (o + co) 0O 0) 04 C) C: C C: 0. 0 0 oo o- T- a- a LO LO LOT-T-T ta a a a a N) a a a a a N o 0 0 0 0 LOL / I 04 UY) C/) eidwex~j ' )U) WO 2011/151368 PCT/EP2O1 1/059024 59 uu) N CN CO CO ~ + 'I'r-'I 0) C D LO LO C: C C: 0. 0 0 CC0 0- 0 a ao N o ol 0 0 0 LOL NL I II 0) 0) ) 0) 0 N I- 0C/00 0C0 ajdwe~j U) U- WO 2011/151368 PCT/EP2O1 1/059024 60 0u) CD CD (+ co -C 04 C 0 0) C C U C: C C: C 0. 0 0 0 0 a a a a a N 2 2 2 2 2 oa a) a) a) a) N CO 0 0) 0 0 0 0)04 0) Nt U') Njwe~ I I. I I. . .
    WO 2011/151368 PCT/EP2O1 1/059024 61 0u) 0C)C LO C0 (o + co' 00'I 0 ))0 C~) o9 L L6 L6 0)1 C C: C: C a2 2 2 2 oo 0 0 0 0C r- 0 0 0 oo a- a- a- a N N I I I I 0Y ) a) a) a) a) N 0)l T- T- T- T N N - - - - I-0 0 0 0 0
    U
    U~La z iz z 00 m- CD ) eidwexj C.0 C C0 N- WO 2011/151368 PCT/EP2O1 1/059024 62 u) UE ) C) CN 'IT o + 0L coC C 5C 0. 0 0 LQ -C o 0 00 CYU) 04 a- a- a a N N I- I- I 0) C)0 ) C) CO 0 0 0 0 L -J )l - 0L 0L 04 C/) 0 0O ajdwx~j l- r- rl U- WO 2011/151368 PCT/EP2O1 1/059024 63 co 0). o LD 00 0 0 0 0 aoT a a a o o a) N NII C: ) C) C) 0 0 0 7 0.10 L- 0 0)6 0 00 ) Cl): WO 2011/151368 64 PCT/EP2011/059024 The following examples illustrate in a non-limiting manner the preparation and efficacy of the compounds of formula (I) according to the invention. 5 Preparation example 1 : preparation of N-cyclopropyl-N-{[dimethyl(phenyl)silyl]methyl}-5-fluoro-1,3 dimethyl-1H-pyrazole-4-carboxamide (compound 8) Step 1 : preparation of N-{[d imethyl(phenyl)silyl]methyl}cyclopropanamine To 5 g (27 mmol) of (chloromethyl)(dimethyl)phenylsilane dissolved in 30 ml of cyclopropylamine, are 10 added 400 mg (2.7 mmol) of sodium iodide. The reaction mixture is stirred for 4 hrs at 450C. The reaction mixture is then cooled to room temperature and concentrated under vacuum. The residue is dissolved in 100 ml of ethyl acetate, washed by brine and dried over magnesium sulfate to yield after concentration 2.75 g of a yellow oil. Distillation yields 1.65 g (30%) of pure N-{[dimethyl(phenyl) silyl]methyl}cyclopropanamine as a yellow oil (M+H = 206). Bp (boiling point) = 1200C (0.1 mmHg). 15 Step 2 : preparation of N-cyclopropyl-N-{[dimethyl(phenyl)silyl]methyl}-5-fluoro-1,3-dimethyl-1H-pyrazole 4-carboxamide At ambient temperature, a solution of 291 mg (1.65 mmol) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4 carbonyl chloride in 2 ml of tetrahydrofurane is added dropwise to a solution of 300 mg (1.5 mmol) of N 20 {[dimethyl(phenyl)silyl]methyl}cyclopropanamine and 0.23 ml (1.65 mmol) of triethylamine in 4 ml of tetrahydrofurane. The reaction mixture is stirred for 2 hrs at 700C. The solvent is removed under vacuum and 100 ml of water are then added to the residue. The watery layer is extracted twice with ethyl acetate (2 x 50 ml) and the combined organic layers are successively washed by a 1 N solution of HCI, a saturated solution of potassium carbonate and brine and dried over magnesium sulfate to yield after 25 concentration 455 mg of a yellow oil. Column chromatography on silica gel (gradient heptane/ethyl acetate) yields 340 mg (60% yield) of N-cyclopropyl-N-{[dimethyl(phenyl)silyl]methyl}-5-fluoro-1,3 dimethyl-1H-pyrazole-4-carboxamide as a colorless oil (M = 345). General preparation example: thionation of amide of formula (I) on Chemspeed apparatus 30 In a 13 ml Chemspeed vial is weighted 0.27mmole of phosphorous pentasulfide (P 2
    S
    5 ). 3 ml of a 0.18 molar solution of the amide (I) (0.54mmole) in dioxane is added and the mixture is heated at reflux for two hours. The temperature is then cooled to 800C and 2.5 ml of water are added. The mixture is heated at 800C for one more hour. 2 ml of water are then added and the reaction mixture is extracted twice by 4 ml of dichloromethane. The organic phase is deposited on a basic alumina cartridge (2g) and eluted twice by 35 8 ml of dichloromethane. The solvents are removed and the crude thioamide derivative is analyzed by LCMS and NMR. Insufficiently pure compounds are further purified by preparative LCMS. Example A: in vivo preventive test on Altemaria solani (tomato) Solvent: 49 parts by weight of N,N-dimethylformamide 40 Emulsifier: 1 part by weight of Alkylarylpolyglycolether WO 2011/151368 65 PCT/EP2011/059024 To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the 5 stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants remain for one day in an incubation cabinet at approximately 220C and a relative atmospheric humidity of 100 %. Then the plants are placed in an incubation cabinet at approximately 200C and a relative atmospheric humidity of 96 %. The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the 10 control while an efficacy of 100 % means that no disease is observed. Under these conditions, good (at least 70 %) to total protection is observed at a dose of 500 ppm of active ingredient with the following compounds from table A: Table A: Example Efficacy Example Efficacy Example Efficacy 1 100 29 94 55 100 2 95 30 95 57 95 4 100 31 100 60 95 9 100 35 90 61 100 10 100 36 100 62 80 11 90 38 94 63 70 12 80 39 94 65 95 15 95 41 100 66 100 16 70 42 100 67 78 17 94 43 100 68 70 18 100 46 95 69 100 19 100 47 100 70 100 20 100 48 100 71 95 21 95 49 94 72 89 22 95 50 100 74 100 25 100 51 95 75 94 26 100 52 100 76 94 27 94 53 80 15 28 100 54 95 Under these conditions, 90% of disease control is observed with compound 11 and 80% of disease control is observed with compound 12 according to the invention whereas no protection at all (0% of disease control) is observed at a dose of 500 ppm with the compound of example 5 disclosed in Gaodeng 20 Xuexiao Huaxue Xuebao (1990), 11(10), 1072-5. Example 5 disclosed in Gaodeng Xuexiao Huaxue Xuebao (1990), 11(10), 1072-5, correspond to the following compound : N-cyclohexyl-N-{[d imethyl(phenyl)silyl]methyl}-2-furamide. These results show that the compounds according to the invention have a much better biological activity than the structurally closest compound disclosed in Gaodeng Xuexiao Huaxue Xuebao (1990), 11(10), 25 1072-5. Example B : in vivo preventive test on Venturia inaequalis (apple scab) WO 2011/151368 66 PCT/EP2011/059024 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of N,N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with 5 the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab (Venturia inaequalis) and then remain for 1 day in 10 an incubation cabinet at approximately 200C and a relative atmospheric humidity of 100 %. The plants are then placed in a greenhouse at approximately 210C and a relative atmospheric humidity of approximately 90 %. The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100 % means that no disease is observed. 15 Under these conditions, high (at least 88 %) to total protection is observed at a dose of 100 ppm of active ingredient with the following compounds from table B Table B: Example Efficacy Example Efficacy Example Efficacy 17 98 28 88 42 99 18 99 31 100 49 96 19 99 38 100 52 100 20 90 39 100 55 100 27 100 41 100 j 20 Example C: in vivo preventive test on Botrvtis cinerea (beans) Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of N,N-dimethylacetamide 25 Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound. After the 30 spray coating has dried on, 2 small pieces of agar covered with growth of Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at 200C and a relative atmospheric humidity of 100 %. 2 days after the inoculation, the size of the lesions on the leaves is evaluated. 0 % means an efficacy which corresponds to that of the control, while an efficacy of 100 % means that no disease is observed. 35 Under these conditions, excellent (at least 95 %) to total protection is observed at a dose of 500 ppm of active ingredient with the following compounds from table C : WO 2011/151368 67 PCT/EP2011/059024 Table C: Example Efficacy Example Efficacy Example Efficacy 19 100 38 95 52 100 27 98 41 98 55 100 31 95 42 100 Example D: in vivo preventive test on Leptosphaeria nodorum (wheat) 5 Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound or the compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 10 To test for protective activity, young plants are sprayed with a preparation of active compound or active compound combination at the stated rate of application. After the spray coating has dried on, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabinet at 200C and a relative atmospheric humidity of 100%. 15 The plants are placed in a greenhouse at a temperature of approximately 150C and a relative atmospheric humidity of approximately 80 %. The test is evaluated 8 days after the inoculation. 0 % means an efficacy which corresponds to that of the untreated control, while an efficacy of 100 % means that no disease is observed. Under these conditions, high (at least 90 %) to total protection is observed at a dose of 500 ppm of active 20 ingredient with the following compounds from table D: Table D: Example Efficacy Example Efficacy Example Efficacy 4 93 27 100 42 100 9 100 28 100 48 100 10 100 30 100 49 94 17 94 31 100 51 80 18 100 32 100 51 95 19 100 38 100 52 100 20 100 39 94 55 100 21 100 41 95 25 Example E: in vivo preventive test on Septoria tritici (wheat) Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is 30 diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application.
    WO 2011/151368 68 PCT/EP2011/059024 After the spray coating has dried on, the plants are sprayed with a spore suspension of Septoria tritici. The plants remain for 48 hours in an incubation cabinet at approximately 200C and a relative atmospheric humidity of approximately 100% and then 60 hours at approximately 150C in a translucent incubation cabinet at a relative atmospheric humidity of approximately 100 %. 5 The plants are placed in a greenhouse at a temperature of approximately 15'C and a relative atmospheric humidity of approximately 80 %. The test is evaluated 21 days after the inoculation. 0 % means an efficacy which corresponds to that of the untreated control, while an efficacy of 100 % means that no disease is observed. Under these conditions, high (at least 90 %) to total protection is observed at a dose of 500 ppm of active 10 ingredient with the following compounds from table E: Table E: Example Efficacy Example Efficacy Example Efficacy 4 100 21 100 40 100 9 93 27 100 41 100 10 100 28 100 42 100 15 90 30 100 49 100 17 83 31 100 51 100 18 100 32 100 52 100 19 100 38 100 55 90 20 92 39 100 15 Example F: in vivo preventive test on Pyrenophora teres (barley) Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with 20 the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Pyrenophora teres. The plants remain for 48 hours in an incubation cabinet at 220C and a 25 relative atmospheric humidity of 100 %. Then the plants are placed in a greenhouse at a temperature of approximately 200C and a relative atmospheric humidity of approximately 80%. The test is evaluated 7-9 days after the inoculation. 0 % means an efficacy which corresponds to that of the untreated control while an efficacy of 100 % means that no disease is observed. Under these conditions, good (at least 70 %) to total protection is observed at a dose of 500 ppm of active 30 ingredient with the following compounds from table F: 35 WO 2011/151368 69 PCT/EP2011/059024 Table F: Example Efficacy Example Efficacy Example Efficacy 1 100 28 100 51 100 2 100 29 95 52 100 4 100 30 100 53 95 9 100 31 100 54 100 10 100 32 95 55 100 11 70 36 100 59 70 12 70 38 100 60 95 15 100 39 100 61 100 17 95 40 95 62 100 18 100 41 100 65 100 19 100 42 10 66 100 20 100 43 100 69 100 21 100 46 100 70 100 22 80 47 95 71 100 25 100 48 100 74 100 26 100 49 100 75 100 27 100 50 1 95 76 - 100 Under these conditions, 70% of disease control is observed with compound 11 and with compound 12 5 according to the invention whereas no protection at all (0% of disease control) is observed at a dose of 500 ppm with the compound of example 5 disclosed in Gaodeng Xuexiao Huaxue Xuebao (1990), 11(10), 1072-5. Example 5 disclosed in Gaodeng Xuexiao Huaxue Xuebao (1990), 11(10), 1072-5, correspond to the following compound : N-cyclohexyl-N-{[d imethyl(phenyl)silyl]methyl}-2-furamide. 10 These results show that the compounds according to the invention have a much better biological activity than the structurally closest compound disclosed in Gaodeng Xuexiao Huaxue Xuebao (1990), 11(10), 1072-5. Example G : in vivo protective test on Phakopsora pachyrhizi (soybean rust) 15 Solvent: 28.5 parts by weight of acetone Emulsifier: 1.5 parts by weight of polyoxyethylene alkyl phenyl ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 20 To test for protective activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after spraying, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust (Phakopsora pachyrhizi). The plants are then placed in a greenhouse at approximately 200C and a relative atmospheric humidity of approximately 80 %. The test is evaluated 11 days after the inoculation. 0 % means an efficacy which corresponds to that of 25 the control, while an efficacy of 100 % means that no disease is observed. Under these conditions, good (at least 80 %) to total protection is observed at a dose of 250 ppm of active ingredient with the following compounds from table G : WO 2011/151368 70 PCT/EP2011/059024 Table G : Example Efficacy Example Efficacy Example Efficacy 18 80 38 85 31 100 52 99 Example H : in vivo preventive test on Puccinia recondita (wheat) 5 Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 10 To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Puccinia recondita. The plants remain for 48 hours in an incubation cabinet at 220C and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 200C and a relative atmospheric humidity of approximately 80%. 15 The test is evaluated 7-9 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed. Under these conditions, 80% of disease control is observed with compound 11 and 40% of disease control is observed with compound 12 according to the invention whereas poor protection (10% of 20 disease control) is observed at a dose of 500 ppm with the compound of example 5 disclosed in Gaodeng Xuexiao Huaxue Xuebao (1990), 11(10), 1072-5. Example 5 disclosed in Gaodeng Xuexiao Huaxue Xuebao (1990), 11(10), 1072-5, correspond to the following compound : N-cyclohexyl-N-{[d imethyl(phenyl)silyl]methyl}-2-furamide. These results show that the compounds according to the invention have a much better biological activity 25 than the structurally closest compound disclosed in Gaodeng Xuexiao Huaxue Xuebao (1990), 11(10), 1072-5. Example I : in vivo test on Puccinia recondita (wheat brown rust) The active ingredients tested are prepared by homogenization in a mixture of acetone/tween/DMSO, then 30 diluted with water to obtain the desired active material. Wheat plants (Scipion variety) sown on 50/50 peat soil pozzolana substrate in starter cups and grown at 120C, are treated at the 1 leaf stage (10 cm tall) by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material. 35 After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores (100,000 spores per ml). The spores are collected from a 10 day old contaminated wheat and are suspended in water containing 2.5 ml/l of tween 80 10%. The contaminated wheat plants are incubated for 24 hours at 200C and at 100% relative humidity, and then for 10 days at 200C and at 70% relative humidity. 40 Grading is carried out 10 days after the contamination, in comparison with the control plants.
    WO 2011/151368 71 PCT/EP2011/059024 Under these conditions, good (at least 70%) or total protection is observed at a dose of 500 ppm of active ingredient with the following compounds: 7. Example J : in vivo test on Alternaria brassicae (leaf spot of crucifers) The active ingredients tested are 5 prepared by homogenization in a mixture of acetone/tween/DMSO, and then diluted with water to obtain the desired active material. Radish plants (Pernot variety), sown on a 50/50 peat soil pozzolana substrate in starter cups and grown at 18 200C, are treated at the cotyledon stage by spraying with the active ingredient prepared as described above. 10 Plants, used as controls, are treated with the mixture of acetone/tween/water not containing the active material. After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Alternaria brassicae spores (40,000 spores per cm3). The spores are collected from a 12 to 13 days old culture. The contaminated radish plants are incubated for 6 7 days at about 180C, under a humid atmosphere. 15 Grading is carried out 6 to 7 days after the contamination, in comparison with the control plants. Under these conditions, good protection (at least 70%) is observed at a dose of 500 ppm of active ingredient with the following compounds: 7 and 8. Example K : in vivo test on Pyrenophora teres (Barley Net blotch) 20 The active ingredients tested are prepared by homogenization in a mixture of acetone/Tween/DMSO, then diluted with water to obtain the desired active material concentration. Barley plants (Plaisant variety), sown on a 50/50 peat soil-pozzolana substrate in starter cups and grown at 120C, are treated at the 1-leaf stage (10 cm tall) by spraying with the active ingredient prepared as described above. 25 Plants, used as controls, are treated with an aqueous solution not containing the active material. After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Pyrenophora teres spores (12,000 spores per ml). The spores are collected from a 12-day-old culture. The contaminated barley plants are incubated for 24 hours at about 200C and at 100% relative humidity, and then for 12 days at 80% relative humidity. 30 Grading is carried out 12 days after the contamination, in comparison with the control plants. Under these conditions, good (at least 70%) is observed at a dose of 500 ppm of active ingredient with the following compound: 7 and 8. Example L : inhibition of aflatoxins Production by Aspergillus parasiticus 35 Compounds were tested in microtiter plates (96 well black flat and transparent bottom) in Aflatoxin inducing liquid media (20g sucrose, yeast extract 4g, KH 2
    PO
    4 1g, and MgSO 4 7H 2 0 0.5g per liter), supplemented with 20 mM of Cavasol (hydroxypropyl-beta-cyclodextrin) and containing 1 % of DMSO. The assay is started by inoculating the medium with a concentrated spore suspension of Aspergillus parasiticus at a final concentration of 1000 spores/ml. 40 The plate was covered and incubated at 200C for 7 days. After 7 days of culture, OD measurement at OD620nm with multiple read per well (circle: 4 x 4) was taken with an Infinite 1000 (Tecan) to calculate the WO 2011/151368 72 PCT/EP2011/059024 growth inhibition. In the same time bottom fluorescence measurement at Em36onm and EX426nm with multiple read per well (square: 3 x 3) was taken to calculate inhibition of aflatoxin formation. Under these conditions, good (at least 80 %) to total inhibition of aflatoxins production and good (at least 70 %) to total growth inhibition of Aspergillus parasiticus is observed at a dose of 50 pM of active 5 ingredient with the following compounds from table L: Table L : % Inhibition of % Inhibition of % Inhibition of % Inhibition of Example Aflatoxin at 50 fungal growth Example Aflatoxin at 50 fungal growth pM at50 pM pM at50pM 1 100 93 55 100 99 2 87 71 60 100 84 4 100 100 61 100 100 15 88 76 65 82 72 18 100 100 66 100 100 25 99 84 67 100 86 26 100 100 69 100 85 31 100 100 70 100 100 36 100 84 72 100 100 38 100 100 74 100 100 46 99 84 75 100 100 47 100 100 76 100 100 52 1 100 1 100 1__ __ _ 1__ _ _ _ _ _ _ _ _
    权利要求:
    Claims (14)
    [1] 1. A compound of formula (I) 3 z 4 z 7 B Si N A Z Z2 Z T 5(I wherein * A represents a carbo-linked, unsaturated or partially saturated, 5-membered heterocyclyl group that can be substituted by up to four groups R ; with the proviso that A is not a non-substituted 2 furyl ring ; 10 e T represents 0 or S; e n represents 0 or 1 ; * B represents a phenyl ring that can be susbtituted by up to 5 groups X which can be the same or different a naphthyl ring that can be susbtituted by up to 7 groups X which can be the same or different a thienyl ring that can be substituted by up to 3 groups X which can be the same or 15 different or a benzothiophenyl ring that can be susbtituted by up to 5 groups X which can be the same or different ; * X represents a halogen atom ; nitro ; cyano; isonitrile ; hydroxy ; amino ; sulfanyl ; pentafluoro-A sulfanyl ; formyl ; formyloxy ; formylamino ; substituted or non-substituted (hydroxyimino)-C-C 8 alkyl ; substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C-C 8 -alkyl ; substituted or non 20 substituted (C 2 -C 8 -alkenyloxyimino)-C-Cs-alky ; substituted or non-substituted (C2-Cs alkynyloxyimino)-C-C 8 -alkyl ; substituted or non-substituted (benzyloxyimino)-C-C 8 -alkyl ; carboxy ; carbamoyl ; N-hydroxycarbamoyl ; carbamate ; substituted or non-substituted Cl-Cs alkyl ; Cl-C8-halogenoalkyl having 1 to 5 halogen atoms ; substituted or non-substituted C2-Cs alkenyl ; C 2 -C8-halogenoalkenyl having 1 to 5 halogen atoms ; substituted or non-substituted C2 25 C8-alkynyl ; C 2 -C8-halogenoalkynyl having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkoxy; Cl-C8-halogenoalkoxy having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylsulfanyl ; Cl-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylsulfinyl ; Cl-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8-alkylsulfonyl ; Cl-C8-halogenoalkylsulfonyl having 1 to 5 30 halogen atoms ; substituted or non-substituted Cl-C8-alkylamino ; substituted or non-substituted di-Cl-C8-alkylamino ; substituted or non-substituted C 2 -C8-alkenyloxy ; C 2 -C8-halogenoalkenyloxy having 1 to 5 halogen atoms ; substituted or non-substituted C 3 -C8-alkynyloxy ; C2-Cs halogenoalkynyloxy having 1 to 5 halogen atoms ; substituted or non-substituted C 3 -C 7 -cycloalkyl ; C 3 -C 7 -halogenocycloalkyl having 1 to 5 halogen atoms ; substituted or non-substituted (C3-C7 35 cycloalkyl)-Cl-C8-alkyl ; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -Cs-alkenyl ; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -Cs-alkyny ; substituted or non-substituted WO 2011/151368 PCT/EP2011/059024 tri(C-C 8 )alkylsilyl ; substituted or non-substituted tri(C-C 8 )alkylsilyl-C-C 8 -alkyl ; substituted or non-substituted C-C 8 -alkylcarbonyl ; C-C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkylcarbonyloxy ; C-C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkylcarbonylamino ; Cl-Cs 5 halogenoalkyl- carbonylamino having 1 to 5 halogen atoms ; substituted or non-substituted Cl-Cs alkoxycarbonyl ; C-C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms ; substituted or non substituted C-C 8 -alkyloxycarbonyloxy ; C-C 8 -halogenoalkoxycarbonyloxy having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkylcarbamoyl ; substituted or non-substituted di-C C 8 -alkylcarbamoyl ; substituted or non-substituted C-C 8 -alkylaminocarbonyloxy ; substituted or 10 non-substituted di-C-C 8 -alkylaminocarbonyloxy ; substituted or non-substituted N-(C-C 8 alkyl)hydroxy carbamoyl ; substituted or non-substituted C-C 8 -alkoxycarbamoyl ; substituted or non-substituted N-(C-C 8 -alkyl)-C-C 8 -alkoxycarbamoy ; aryl that can be susbtituted by up to 6 groups Q which can be the same or different ; C-C 8 -arylalkyl that can be susbtituted by up to 6 groups Q which can be the same or different C 2 -C 8 -arylalkenyl that can be susbtituted by up to 6 15 groups Q which can be the same or different; C 2 -C 8 -arylalkynyl that can be susbtituted by up to 6 groups Q which can be the same or different ; aryloxy that can be susbtituted by up to 6 groups Q which can be the same or different ; arylsulfanyl that can be susbtituted by up to 6 groups Q which can be the same or different ; arylamino that can be susbtituted by up to 6 groups Q which can be the same or different ; C-C 8 -arylalkyloxy that can be susbtituted by up to 6 groups Q 20 which can be the same or different ; C-C 8 -arylalkylsulfanyl that can be susbtituted by up to 6 groups Q which can be the same or different ; or C-C 8 -arylalkylamino that can be susbtituted by up to 6 groups Q which can be the same or different ; * two substituent X together with the consecutive carbon atoms to which they are linked can form a
    [2] 5- or 6-membered, saturated carbocycle or saturated heterocycle, which can be substituted by up 25 to four groups Q which can be the same or different ; e Z' and Z2 independently represent a hydrogen atom ; a halogen atom ; cyano ; substituted or non-substituted C-C 8 -alkyl ; C-C 8 -halogenoalkyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkoxy; substituted or non-substituted C-C 8 -alkylsulfanyl; or substituted or non-substituted C-C 8 -alkoxycarbonyl ; or Z' and Z2 are a C 2 -C 5 -alkylene group that can be 30 substituted by up to four C-C 8 -alkyl groups ; * Z 3 and Z 4 independently represent a substituted or non-substituted C-C 8 -alkyl; Z5 and Z6 independently represent a hydrogen atom ; a halogen atom ; cyano ; substituted or non-substituted C-C 8 -alkyl ; C-C 8 -halogenoalkyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkoxy; substituted or non-substituted C-C 8 -alkylsulfanyl; or substituted or 35 non-substituted C-C 8 -alkoxycarbonyl ; or Z5 and Z6 are a C 2 -C 5 -alkylene group that can be substituted by up to four C-C 8 -alkyl groups ; * Z 7 represents a hydrogen atom ; a formyl group; a substituted or non-substituted C-C 8 -alkyl ; a substituted or non substituted C-C 8 -alkoxy; a non-substituted C 3 -C 7 -cycloalkyl or a C3-C7 cycloalkyl substituted by up to 10 atoms or groups that can be the same or different and that can 40 be selected in the list consisting of halogen atoms, cyano, C-C 8 -alkyl, C-C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, C-C 8 -alkoxy, Cl-C8 halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different, Cl-C8- WO 2011/151368 75 PCT/EP2011/059024 alkoxycarbonyl, C-C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different, C-C 8 -alkylaminocarbonyl and di-C-C 8 -alkylaminocarbonyl ; e Q independently represents a halogen atom ; cyano ; nitro ; substituted or non-substituted Cl-C8 alkyl ; C-C 8 -halogenoalkyl having 1 to 9 halogen atoms that can be the same or different ; 5 substituted or non-substituted C-C 8 -alkoxy ; C-C 8 -halogenoalkoxy having 1 to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 8 -alkylsulfanyl ; Cl-C8 halogenoalkylsulfanyl having 1 to 9 halogen atoms that can be the same or different ; substituted or non-substituted tri(C-C 8 )alkylsilyl ; substituted or non-substituted tri(C-C 8 )alkylsilyl-C-C 8 -alky ; substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C-C 8 -alkyl ; substituted or non-substituted 10 (benzyloxyimino)-C-C 8 -alkyl ; * R independently represents hydrogen atom ; halogen atom ; nitro ; cyano ; hydroxy ; amino sulfanyl ; pentafluoro-A 6 -sulfanyl ; substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C-C 8 -alkyl substituted or non-substituted (benzyloxyimino)-Cl-C 8 -alkyl substituted or non-substituted Cl-Cs alkyl ; C-C 8 -halogenoalkyl having 1 to 5 halogen atoms ; substituted or non-substituted C2-Cs 15 alkenyl ; C 2 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms ; substituted or non-substituted C2 C 8 -alkynyl ; C 2 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkoxy; C-C 8 -halogenoalkoxy having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkylsulfanyl ; C-C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkylsulfinyl ; C-C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms ; 20 substituted or non-substituted C-C 8 -alkylsulfonyl ; C-C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkylamino ; substituted or non-substituted di-C-C 8 -alkylamino ; substituted or non-substituted C 2 -C 8 -alkenyloxy ; substituted or non substituted C 3 -C 8 -alkynyloxy ; substituted or non-substituted C 3 -C 7 -cycloalkyl ; C3-C7 halogenocycloalkyl having 1 to 5 halogen atoms ; substituted or non-substituted tri(C-C 8 )alkylsilyl 25 ; substituted or non-substituted C-C 8 -alkylcarbonyl ; C-C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms ; substituted or non-substituted C-C 8 -alkoxycarbonyl ;C-C8 halogenoalkoxycarbonyl having 1 to 5 halogen atoms ; substituted or non-substituted Cl-C8 alkylcarbamoyl ; substituted or non-substituted di-C-C 8 -alkylcarbamoyl ; phenoxy phenylsulfanyl ; phenylamino ; benzyloxy; benzylsulfanyl ; or benzylamino; 30 as well as its salts, N-oxydes, and optically active isomers. 2. A compound according to claim 1 wherein A is selected in the list consisting of: - a heterocycle of formula (A 1 ) R2 R1 R / R3 35 (A 1 ) wherein R1 to R3 that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same WO 2011/151368 76 PCT/EP2011/059024 or different ; substituted or non-substituted C-C 5 -alkoxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different providing that a least one of the substituent R 1 to R 3 is not a hydrogen atom ; 5 - a heterocycle of formula (A 2 ) R 6 RSR (A 2 ) wherein R4 to R6 that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 10 non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 5 -alkoxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; - a heterocycle of formula (A 3 ) R 7 N ~N N 15 R (A 3 ) wherein R 7 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non 20 substituted C-C 5 -alkoxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; R represents a hydrogen atom or a substituted or non-substituted C-C 5 -alkyl; - a heterocycle of formula (A 4 ) R 10 R1 25 R S (A 4 ) wherein R9 to R" that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; amino ; substituted or non-substituted C-C 5 -alkoxy ; substituted or non 30 substituted C-C 5 -alkylsulfanyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; WO 2011/151368 PCT/EP2011/059024 - a heterocycle of formula (A 5 ) / (A 5 ) 5 wherein R and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy ; amino ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; 10 R represents a hydrogen atom a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy; amino ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; 15 - a heterocycle of formula (A 6 ) R 16 R' / N R1 17 (A 6 ) wherein 20 R 15 represents a hydrogen atom ; a halogen atom ; a cyano ; substituted or non-substituted C-C 5 -alkyl substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R16 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 25 non-substituted C-C 5 -alkoxycarbonyl ; substituted or non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R 17 represent a hydrogen atom or substituted or non-substituted C-C 5 -alkyl 30 - a heterocycle of formula (A 7 ) R22 R21 R R 2 N R" 19 R WO 2011/151368 78 PCT/EP2011/059024 (A 7 ) wherein R 19 represents a hydrogen atom or a C-C 5 -alkyl R to R that can be the same or different represent a hydrogen atom a halogen atom ; substituted or 5 non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; - a heterocycle of formula (A 8 ) R 2 N R2 10 (A 8 ) wherein R 23 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl 15 comprising up to 9 halogen atoms that can be the same or different; - a heterocycle of formula (A 9 ) N R26 R2 Re RM (A 9 ) 20 wherein R 25 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R 2 represents a hydrogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different 25 - a heterocycle of formula (A 10 ) N R282 R s S (A 10 ) wherein 30 R 27 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; C-C 5 -halogenoalkoxy WO 2011/151368 PCT/EP2011/059024 comprising up to 9 halogen atoms that can be the same or different ; amino substituted or non substituted C-C 5 -alkylamino or substituted or non-substituted di(C-C 5 -alkyl)amino; - a heterocycle of formula (All) N R 30 R29 5 S (A1) wherein R 2 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the 10 same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R 3 0 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; C1-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; amino ; substituted or non 15 substituted C-C 5 -alkylamino or substituted or non-substituted di(C-C 5 -alkyl)amino; - a heterocycle of formula (A 12 ) / N R321)N N 131 R (A 1 2) 20 wherein R 31 represents a hydrogen atom or a substituted or non-substituted C-C 5 -alkyl R 32 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C1-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R 3 3 represents a hydrogen atom ; a halogen atom ; a nitro ; substituted or non-substituted C-C 5 -alkyl 25 substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; - a heterocycle of formula (A 13 ) / N R 35 N R3 N 136 30 R (A 13 ) WO 2011/151368 80 PCT/EP2011/059024 wherein : R 3 4 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted or non-substituted C 3 -C 5 -cycloalkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 5 -alkoxy ; substituted or non-substituted C2-Cs 5 alkynyloxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R 35 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; a cyano substituted or non-substituted C-C 5 -alkoxy ; substituted or non-substituted C-C 5 -alkylsulfanyl ; Cl-Cs halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; amino ; substituted or non 10 substituted C-C 5 -alkylamino or substituted or non-substituted di(C-C 5 -alkyl)amino; R 3 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl; -a heterocycle of formula (A 1 4 ) R38 R37 R R N N 139 15 (A 14 ) wherein R 3 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 5 -alkoxy or a substituted or non-substituted C1-Cs 20 alkylsulfanyl R 3 9 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl - a heterocycle of formula (A 15 ) R 41 N R 25 (A 15 ) wherein R and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; 30 - a heterocycle of formula (A 16 ) R42 N/ No R4 WO 2011/151368 81 PCT/EP2011/059024 (A 1 6) wherein R42 and R43 that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same 5 or different or amino ; -a heterocycle of formula (A 17 ) R 45 R 44 N'* 0 (A 1 7) 10 wherein R44 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; 15 - a heterocycle of formula (A 18 ) R47 N/ N S R 4 6 (A 1 8) wherein R 4 7 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C1-C5 20 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R 4 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; C1-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or substituted or non substituted C-C 5 -alkylsulfanyl 25 - a heterocycle of formula (A 19 ) R49 R48 R4 R4 S (A 1 9) wherein R49 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 30 non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; WO 2011/151368 82 PCT/EP2011/059024 - a heterocycle of formula (A 20 ) R 5 0 S (A 20) 5 wherein R and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted or non-substituted C-C 5 -alkoxy ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different 10 -a heterocycle of formula (A 21 ) 52 N' N -S (A 1) wherein 15 R 52 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different. -a heterocycle of formula (A 22 ) R 5 N N S 20 (A 22 ) wherein R 53 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or Cl-C5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different. 25 -a heterocycle of formula (A 23 ) R 5 N NN R (A 3) wherein WO 2011/151368 83 PCT/EP2011/059024 R54 and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R 55 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl 5 -a heterocycle of formula (A 24 ) R57 N N, 5 8 R (A 24 ) wherein 10 R and R that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R 58 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl 15 -a heterocycle of formula (A 25 ) R60 R61 RG RS N N R62 (A 25) wherein R60 and R61 that can be the same or different represent a hydrogen atom ; a halogen atom ; substituted or 20 non-substituted C-C 5 -alkyl or C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; R62 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl; -a heterocycle of formula (A 26 ) R 65 R63 NN 164 25 R (A 26 ) wherein R 6 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; substituted or non-substituted C 3 -C 5 -cycloalkyl ; C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be WO 2011/151368 84 PCT/EP2011/059024 the same or different ; substituted or non-substituted C-C 5 -alkoxy ; substituted or non-substituted C2-C5 alkynyloxy or C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R 6 represents a hydrogen atom ; a halogen atom ; substituted or non-substituted C-C 5 -alkyl ; a cyano substituted or non-substituted C-C 5 -alkoxy ; substituted or non-substituted C-C 5 -alkylsulfanyl ; Cl-C5 5 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; C-C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; amino ; substituted or non substituted C-C 5 -alkylamino or di(C-C 5 -alkyl)amino; R64 represents a hydrogen atom or substituted or non-substituted C-C 5 -alkyl. 10 3. A compound according to claim 2 wherein A is selected in the list consisting of A2 ; A6 ; A1 and A1 4. A compound according to claim 3 wherein A represents A wherein R34 represents a substituted or non-substituted C-C 5 -alkyl, C-C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 5 -alkoxy ; R 35 represents a hydrogen atom or a halogen 15 atom and R represents a substituted or non-substituted C-C 5 -alkyl. 5. A compound according to any one of claims 1 to 4 wherein T represents 0.
    [3] 6. A compound according to any one of claims 1 to 5 wherein B represents a substituted or non 20 substituted phenyl ring or a substituted or non-substituted naphthyl ring.
    [4] 7. A compound according to claim 6 wherein B represents a substituted or non-substituted phenyl ring.
    [5] 8. A compound according to any one of claims 1 to 7 wherein X independently represents a halogen 25 atom ; substituted or non-substituted C-C 8 -alkyl ; C-C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different ; substituted or non-substituted tri(C-C 8 -alkyl)silyl ; substituted or non substituted C-C 8 -alkoxy or C-C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; or wherein two consecutive substituents X together with the phenyl ring form a substituted or non substituted 1,3-benzodioxolyl ; 1,2,3,4-tetrahydro-quinoxalinyl ; 3,4-dihydro-2H-1,4 30 benzoxazinyl; 1 ,4-benzodioxanyl ; indanyl ; 2,3-dihydrobenzofuranyl ; or indolinyl.
    [6] 9. A compound according to any one of claims 1 to 8 wherein Z , Z 2, Z and Z 6 independently represent a hydrogen atom, a substituted or non-substituted C-C 8 -alkyl or a substituted or non-substituted Cl-Cs alkoxy. 35
    [7] 10. A compound according to any one of claims 1 to 9 wherein Z3 and Z4 independently represent a non substituted Cl-C 8 -alkyl.
    [8] 11. A compound according to claim 10 wherein Z 3 and Z 4 independently represent a non-substituted Cj 40 C 3 -alkyl. WO 2011/151368 85 PCT/EP2011/059024
    [9] 12. A compound according to any one of claims 1 to 11 wherein Z 7 represents a hydrogen atom, a non substituted C3-C7 cycloalkyl or a C3-C7 cycloalkyl substituted by up to 10 groups or atoms that can be the same or different and that can be selected in the list consisting of halogen atoms, C-C 8 -alkyl, Cl-C8 halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, C-C 8 -alkoxy or Cl-C8 5 halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different.
    [10] 13. A compound according to claim 12 wherein Z 7 represents a non-substituted C 3 -C 7 -cycloalkyl.
    [11] 14. A compound according to claim 13 wherein Z 7 represents cyclopropyl. 10
    [12] 15. A compound according to any one of claims 1 to 14 wherein R independently represents a hydrogen atom ; halogen atom ; cyano substituted or non-substituted C-C 8 -alkylamino substituted or non substituted di-C-C 8 -alkylamino substituted or non-substituted tri(C-C 8 -alkyl)silyl substituted or non substituted C-C 8 -alkyl ; C-C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or 15 different ; substituted or non-substituted C-C 8 -alkoxy ; C-C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different ; substituted or non-substituted C-C 8 -alkylsulfanyl ; amino ; hydroxyl ; nitro ; substituted or non-substituted C-C 8 -alkoxycarbonyl ; substituted or non-substituted C2 C 8 -alkynyloxy. 20 16. A fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) according to claims 1 to 15 and an agriculturally acceptable support, carrier or filler.
    [13] 17. A compound of formula (II) Z,, ,Z4H B Si Z Z 2 Z Z 25 wherein B, n, Z1, Z2, Z3, Z4, Z5 and Z6 are as defined in any one of claims 1 to 15, and Z 7 represents a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group with the exclusion of N-{[dimethyl (phenyl)silyl]methyl}cyclohexanamine.
    [14] 18. A method for controlling phytopathogenic fungi of crops, characterized in that an agronomically 30 effective and substantially non-phytotoxic quantity of a compound according to claims 1 to 15 or a composition according to claim 16 is applied to the soil where plants grow or are capable of growing, to the leaves and/or the fruit of plants or to the seeds of plants. 35
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    同族专利:
    公开号 | 公开日
    MX2012013898A|2012-12-17|
    WO2011151368A3|2012-03-08|
    KR20130109959A|2013-10-08|
    CO6660481A2|2013-04-30|
    US20130065855A1|2013-03-14|
    JP2013533854A|2013-08-29|
    CN102933590A|2013-02-13|
    US9556205B2|2017-01-31|
    UA110703C2|2016-02-10|
    CA2796125A1|2011-12-08|
    JP5847169B2|2016-01-20|
    CA2796125C|2018-07-17|
    WO2011151368A2|2011-12-08|
    CL2012003333A1|2013-01-25|
    EP2576571B1|2017-01-25|
    AR081833A1|2012-10-24|
    AU2011260331B2|2014-04-17|
    CN102933590B|2016-05-18|
    BR112012030584A2|2017-06-27|
    EP2576571A2|2013-04-10|
    BR112012030584B1|2019-01-22|
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    法律状态:
    2014-08-14| FGA| Letters patent sealed or granted (standard patent)|
    2017-01-05| MK14| Patent ceased section 143(a) (annual fees not paid) or expired|
    优先权:
    申请号 | 申请日 | 专利标题
    EP10356018.1||2010-06-03||
    EP10356018||2010-06-03||
    US36800710P| true| 2010-07-27|2010-07-27||
    US61/368,007||2010-07-27||
    PCT/EP2011/059024|WO2011151368A2|2010-06-03|2011-06-01|Fungicide n-[methyl]-carboxamide derivatives|
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