Piperazine compounds having herbicidal action

Details Piperazine compounds having herbicidal action Piperazine compounds having herbicidal action

C - Chemistry, Metallurgy

07

D

C07D 241/08 (2006.01) A61K 31/495 (2006.01) C07D 403/10 (2006.01) C07D 407/10 (2006.01) C07D 409/10 (2006.01) C07D 413/10 (2006.01) C07D 417/10 (2006.01)

Patent

CA 2689209

The invention relates to piperazine compounds of the following defined general formula (I) and to their use as herbicides. The invention also relates to crop protection agents and to a method for combating undesired plant growth. In formula (I), the variables are defined as follows: R1 is selected from halogen, cyano, nitro, Z-C(=O)-R11, phenyl and a 5- or 6-membered heterocyclic group that has 1, 2, 3 or 4 heteroatoms, selected from O, N and S as ring atoms, wherein phenyl and the heterocyclic group are unsubstituted or have 1, 2, 3 or 4 substituents R1a; Z stands for a covalent bond or a CH2 group; R11 represents hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C5-C6 cycloalkenyl, C2-C6 alkynyl and similar; R2 represents hydrogen, halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C2- C4 alkenyl, C1-C4 alkoxy, C1-C4 haloalkoxy, benzyl or a group S(O) nR21, wherein R21 stands for C1-C4 alkyl or C1-C4 haloalkyl and n stands for 0, 1 or 2; R3 represents hydrogen or halogen; R4 represents C1-C4 alkyl, C3- C4 alkenyl or C3-C4 alkynyl; R5 represents hydrogen, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl or a group (=O)R51, wherein R51 stands for hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R6 stands for C1-C4 alkyl, C1-C4 hydroxy alkyl or C1-C4 haloalkyl; R7, R8 stand, independently of one another, for hydrogen, OH, C1-C4 alkoxy, C1-C4 haloalkyoxy, C1-C4 alkyl or C1-C4 haloalkyl; R9, R10 are selected, independently of one another, from hydrogen, halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C1-C4alkoxy and C1-C4 haloalkoxy.

La présente invention concerne des composés pipéraziniques représentés par la formule générale suivante (I) et leur utilisation comme herbicides. L'invention concerne également un agent phytosanitaire et un procédé de lutte contre les végétations indésirables. Dans cette formule (I), R1 est choisi parmi les halogène, cyano, nitro, Z-C(=O)-R11, phényle et un reste hétérocyclique à 5 ou 6 segments dont 1, 2, 3 ou 4 hétéroatomes sont choisis parmi O, N et S, le phényle et le reste hétérocyclique étant éventuellement 1, 2, 3 ou 4 substitués par R1a, Z représentant une liaison covalente ou un groupe CH2, R11 étant hydrogène, C1-C6-alkyle, C3-C6-cycloalkyle, C2-C6-alcényle, C5-C6-cycloalcényle, C2-C6-alkynyle ou équivalent. R2 est hydrogène, halogène, nitro, cyano, C1-C4-alkyle, C1-C4-haloalkyle, C2-C4-alcényle, C1-C4-alcoxy, C1-C4-haloalcoxy, benzyle ou un groupe S(O)nR21 dans lequel R21 est C1-C4-alkyle ou C1-C4-haloalkyle, et n vaut 0, 1 ou 2. R3 est hydrogène ou halogène. R4 est C1-C4-alkyle, C3-C4-alcényle ou C3-C4-alkynyle. R5 est hydrogène, C1-C4-alkyle, C3-C4-alcényle, C3-C4-alkynyle, ou un groupe C(=O)R51, R51 étant hydrogène, C1-C4-alkyle, C1-C4-haloalkyle, C1-C4-alcoxy ou C1-C4-haloalcoxy. R6 est C1-C4-alkyle, C1-C4-hydroxyalkyle, ou C1-C4-haloalkyle. R7 et R8 sont indépendamment l'un de l'autre hydrogène, OH, C1-C4-alcoxy, C1-C4-haloalcoxy, C1-C4-alkyle ou C1-C4-haloalkyle. Enfin, R9 et R10 sont indépendamment l'un de l'autre hydrogène, halogène CN, NO2, C1-C4-alkyle, C1-C4-haloalkyle, C2-C4-alcényle, C1-C4-alcoxy ou C1-C4-haloalcoxy.

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