Esters of non- aromatic heterocyclic compounds having a nematocidal activity, their agronomic compositions and use thereof

A non-aromatic heterocyclic compound with 5 or 6 terms, substituted in position 2 with a fluoroalkenyl chain, having a general formula (I):

• wherein:
• E represents an oxygen atom, a sulfur atom or an N-A group;
• Y represents a sulfur atom optionally oxidized to group S(O) or S(O)2, an oxygen atom, an NR7 group or a CH2 group;
• -A represents a hydrogen atom, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C2-C7 alkenyl group, a C2-C7 haloalkenyl group, a C3-C6-cycloalkyl group, a C3-C6-cycloalkylalkylC1-C6 group, a C1-C6-alkylsulfinyl group, a C1-C6-alkylsulfonyl group, a C1-C6-haloalkylsulfonyl group, an arylsulfonyl group, a C1-C6-alkanoyl group, a formyl group, a C1-C6-haloalkanoyl group, a C3-C6-cycloalkanoyl group, an aroyl group, a heterocyclylcarbonyl group, a C1-C6-thioalkanoyl group, a C1-C6-thiohaloalkanoyl group, a C3-C6-thiocycloalkanoyl group, a thioaroyl group, a thioheterocyclylcarbonyl group, a C1-C6-alkoxycarbonyl group, a C1-C6-haloalkoxycarbonyl group, a C3-C6 cycloalkoxycarbonyl group, an aryloxycarbonyl group, a benzyloxycarbonyl group, a heterocyclyloxycarbonyl group, a C1-C6-alkylthiocarbonyl group, a C1-C6-haloalkylthiocarbonyl group, a C3-C6 cycloalkylthiocarbonyl group, an arylthiocarbonyl group, a benzoylthiocarbonyl group, a heterocyclylthiocarbonyl group, a C1-C6-alkylaminocarbonyl group, a C1-C6-dialkylaminocarbonyl group, a C1-C6-haloalkylaminocarbonyl group, a C1-C6-dihaloalkylaminocarbonyl group, a C3-C6 cycloalkylaminocarbonyl group, a C1-C6-dicycloalkylaminocarbonyl group, an arylaminocarbonyl group, a heterocyclylaminocarbonyl group, a C1-C6-alkyl-carbonylalkyl-C1-C6 group, a C1-C6-haloalkyl-carbonylalkyl-C1-C6 group, a C3-C6 cycloalkylcarbonylalkyl-C1-C6 group, an arylcarbonylalkyl-C1-C6 group, a benzylcarbonylalkyl-C1-C6 group, a heterocyclycarbonylalkyl-C1-C6 group, a C1-C6-alkyl-carbonyloxyalkyl-C1-C6 group, a C1-C6-alkyl-carbonyloxyhaloalkyl-C1-C6 group, a C1-C6-alkyl-carbonyloxycycloalkyl-C3-C6 group, a C1-C6-alkyl-carbonyloxyaryl group, a C1-C6-alkyl-carbonyloxybenzyl group, a C1-C6-alkyl-carbonyloxyheterocyclic group;
• a C1-C6-alkyl-carbonylthioalkyl-C1-C6 group, a C1-C6-alkyl-carbonylthiohaloalkyl-C1-C6 group;
• a C1-C6-alkyl-carbonylthiocycloalkyl-C3-C6 group, a C1-C6-alkyl-carbonylthioaryl group, a C1-C6-alkyl-carbonylthiobenzyl group, a C1-C6-alkyl-carbonylthioheterocyclic group, a C1-C6-alkyl-aminocarbonylalkyl-C1-C6 group, a C1-C6-haloalkyl-aminocarbonylalkyl-C1-C6 group, a C1-C6-dialkyl-aminocarbonylalkyl-C1-C6 group, a C1-C6-dihaloalkyl-aminocarbonylalkyl-C1-C6 group, a C3-C6-cycloalkylamino-carbonyl-alkyl-C1-C6 group, a C6-C12-dicycloalkyl-aminocarbonylalkyl-C1-C6 group, an aryl-aminocarbonylalkyl-C1-C6 group, a benzyl-aminocarbonylalkyl-C1-C6 group, a heterocyclyl-aminocarbonylalkyl-C1-C6 group, a C1-C6-alkanoyloxyalkyl-C1-C6 group, a C1-C6-haloalkanoyloxyalkyl-C1-C6 group, a C3-C6-cycloalkanoyloxyalkyl-C1-C6 group, an aroyloxyalkyl-C1-C6 group, a benzoyloxyalkyl-C1-C6 group, a heterocyclylcarbonyloxyalkyl-C1-C6 group, a C1-C6-alkoxyalkyl-C1-C6 group, a C1-C6-haloalkoxyalkyl-C1-C6 group, a C3-C6-cycloalkoxyalkyl-C1-C6 group, an aryloxyalkyl-C1-C6 group, a benzyloxyalkyl-C1-C6 group, a heterocyclyloxyalkyl-C1-C6 group, a C1-C6-alkanoylthioalkyl-C1-C6 group, a C1-C6-haloalkanoylthioalkyl-C1-C6 group, a C3-C6-cycloalkanoylthioalkyl-C1-C6 group, an aroylthioalkyl-C1-C6 group, a benzoylthioalkyl-C1-C6 group, a heterocyclylcarbonylthioalkyl-C1-C6 group, a C1-C6-alkylthioalkyl-C1-C6 group, a C1-C6-haloalkylthioalkyl-C1-C6 group, a C3-C6-cycloalkylthioalkyl-C1-C6 group, an arylthioalkyl-C1-C6 group, a benzylthioalkyl-C1-C6 group, a heterocyclylthioalkyl-C1-C6 group, a C1-C6-alkanoylaminoalkyl-C1-C6 group, a C1-C6-haloalkanoylaminoalkyl-C1-C6 group, a C3-C6-cycloalkanoylaminoalkyl-C1-C6 group, an aroylaminoalkyl-C1-C6 group, a benzoylaminoalkyl-C1-C6 group, a heterocyclylcarbonylaminoalkyl-C1-C6 group, a C1-C6-dialkylphosphoryl group, a diarylphosphoryl group, a C1-C6-dialkylthiophosphoryl group, a diarylthiophosphoryl group, a 2-oxa-1,3,2-dioxaphosphorinan-2-yl group optionally possibly substituted by one or more C1-C6 alkyl groups, a 2-oxa-1,3,2-dioxaphospholan-2-yl group optionally possibly substituted by one or more C1-C6 alkyl groups;
• Z represents a C═O bond, a C═S bond or a R1—C—R2 group:
• n represents an integer ranging from 0 to 1;
• m represents an integer ranging from 1 to 6;
• X represents a hydrogen or fluorine atom;
• R1 and R2 are the same or different and represent a hydrogen atom, a halogen atom selected from fluorine, chlorine, bromine or iodine, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C7 alkenyl group, a C2-C7 haloalkenyl group, a C3-C6-cycloalkyl group, an aryl group, a heterocyclic group, a C3-C6-cycloalkylalkyl-C1-C6 group, a C1-C6-alkoxycarbonyl group, a C1-C6-haloalkoxycarbonyl group, a C3-C6 cycloalkoxycarbonyl group, an aryloxycarbonyl group, a heterocyclyloxycarbonyl group, a C1-C6-alkylthiocarbonyl group, a C1-C6-haloalkylthiocarbonyl group, a C3-C6 cycloalkylthiocarbonyl group, an arylthiocarbonyl group, a heterocyclylthiocarbonyl group, a C1-C6-alkylaminocarbonyl group, a C1-C6-dialkylaminocarbonyl group, a C1-C6-haloalkylaminocarbonyl group, a C1-C6-dihaloalkylaminocarbonyl group, a C3-C6 cycloalkylaminocarbonyl group, a C3-C6 dicycloalkylaminocarbonyl group, an arylaminocarbonyl group, a heterocyclylaminocarbonyl group, a nitrile, a C1-C6-alkoxyl group, a C1-C6-thioalkoxyl group, a C1-C6-haloalkoxyl group, a C3-C6-cycloalkoxyl group, a C1-C6-halothioalkoxyl group, a C3-C6-cyclothioalkoxyl group, a C1-C6-alkanoyl group, a C1-C6-haloalkanoyl group, a C3-C6 cycloalkanoyl group, an aroyl group, a heterocyclylcarbonyl group, a glucosyl group, galactosyl, mannosyl, saccharosyl, lactosyl, maltosyl, arabisonyl, xylosyl, ribosyl, aminoglucosyl, N-acetylaminoglucosyl wherein the OH groups present on said sugars can be optionally substituted to form OR7 groups;
• or R1 and R2 together with the carbon atom to which they are bound form a C3-C6 cycloalkyl ring;
• R7 represents a C1-C6 alkyl group, a benzyl group, a C1-C6-alkanoyl group;
• R3, R4, R5 and R6 are the same or different, and represent a hydrogen atom, a halogen atom selected from the group consisting of fluorine, chlorine, bromine or iodine, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C3-C6 cycloalkyl group, an aryl group, a benzyl group, and a heterocyclic group;
• excluding the compound wherein:
• E=N-A;
• A=benzyloxycarbonyl;
• Z═Y═CH2;
• R3═R4═H;
• n=0;
• m=2;
• X═F.