Substituted pyrazole-3-yl benzazoles

Details Substituted pyrazole-3-yl benzazoles Substituted pyrazole-3-yl benzazoles

C - Chemistry, Metallurgy

07

D

C07D 417/04 (2006.01) A01N 43/56 (2006.01) A01N 43/74 (2006.01) C07D 413/04 (2006.01) C07D 413/10 (2006.01) C07D 417/10 (2006.01)

Patent

CA 2275611

The invention concerns substituted pyrazole-3-yl benzazoles of formula (I) and salts thereof, in the formula R1 designating H, C1-C4 alkyl, C1-C4 alkyl halide; R2 designating CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4- haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulphinyl, C1-C4- haloalkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylsulphonyl; R3 = H, CN, NO2, halogen, C1-C4-alkyl, C1-C4-haloalkyl; R4 designating H, halogen; R5 designating H, CN, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1- C4-haloalkoxy; Z designating -N=C(XR6)-O- or -N=C(XR6)-S-, bonded to .alpha. by the nitrogen, oxygen or sulphur; X designating a chemical bond, oxygen, sulphur, -S(O)-, -SO2-, -NH- or -N(R7); R6, R7 designating C1-C6-alkyl, C1-C6- haloalkyl, cyano-C1-C4-alkyl, hydroxy-C1-C4-alkyl, C3-C6-alkenyl, cyano-C3-C6- alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, cyano-C3-C6-alkinyl, C3-C6- haloalkinyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C3-C4- alkenyloxy-C1-C4-alkyl, C3-C4-alkinyloxy-C1-C4-alkyl, C3-C8-cycloalkyloxy-C1- C4-alkyl, amino-C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, di(C1-C4- alkyl)amino-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-haloalkylthio-C1- C4-alkyl, C3-C4-alkenylthio- C1-C4-alkyl, C3-C4-alkinylthio-C1-C4-alkyl, C1-C4- alkyl-sulphinyl-C1-C4-alkyl, C1-C4-haloalkylsulphinyl-C1-C4-alkyl, C3-C4- alkenylsulphinyl-C1-C4-alkyl, C3-C4-alkinylsulphinyl-C1-C4-alkyl, C1-C4- alkylsulphonyl-C1-C4-alkyl, C1-C4-haloalkylsulphonyl-C1-C4-alkyl, C3-C4- alkenylsulphonyl-C1-C4-alkyl, C3-C4-alkinylsulphonyl-C1-C4-alkyl, hydroxycarbonyl-C1-C4-alkyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, which can carry a CN oder C1-C4-alkoxycarbonyl group, C1-C4-alkylthiocarbonyl-C1-C4-alkyl, aminocarbonyl-C1-C4-alkyl, C1-C4-alkylaminocarbonyl-C1-C4-alkyl, di(C1-C4- alkyl)aminocarbonyl-C1-C4-alkyl, di(C1-C4-alkyl)-phosphonyl-C1-C4-alkyl, C1-C4- alkoxyimino-C1-C4-alkyl, C3-C4-alkenyloxyimino-C1-C4-alkyl, optionally substituted C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1- C4-alkyl, 3- to 7-member heterocyclic or heterocyclyl-C1-C4-alkyl, wherein each cycloalkyl ring and each heterocyclyl ring contain a CO or CS ring member; if X is a chemical bond, -O-, -S-, -NH- or -N(R7)-, R6 also being C1- C4 alkylcarbonyl, C1-C4 haloalkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkylsulphonyl or C1-C4 haloalkylsulphonyl; if X is a chemical bond, R6 additionally designating CN, SH, NH2, halogen, -CH2-CH(halogen)-R8, -CH=CH-R8 or -CH=C(halogen)-R8, R8 designating COOH, C1-C4 alkoxycarbonyl, C1-C4 alkylthiocarbonyl, CONH2, C1-C4 alkylaminocarbonyl, di(C1-C4 alkyl)aminocarbonyl or di(C1-C4 alkyl)phosphonyl; or R6 plus R7 designating an optionally substituted 1,3-propylene, tetramethylene, pentamethylene or ethylene oxyethylene chain. The invention alsoEncerns the use of these substances as herbicides and for the desiccation and/or defoliation of plants.

L'invention concerne des pyrazol-3-ylbenzazoles substitués de la formule (I), et des sels de ceux-ci, formule (I) dans laquelle: R?1¿ représente H, alkyle C¿1?-C¿4?, halogénure d'alkyle C¿1?-C¿4?; R?2¿ représente CN, alkyle C¿1?-C¿4?, haloalkyle C¿1?-C¿4?, alcoxy C¿1?-C¿4?, haloalcoxy C¿1?-C¿4?, alkyl C¿1?-C¿4?-thio, haloalkyle C¿1?-C¿4?-thio, alkyle C¿1?-C¿4?-sulfinyle, haloalkyle C¿1?-C¿4?-sulfinyle, alkyl C¿1?-C¿4?-sulfonyle, haloalkyle C¿1?-C¿4?-sulfonyle; R?3¿ représente H, CN, NO¿2?, halogène, alkyle C¿1?-C¿4?, haloalkyle C¿1?-C¿4?; R?4¿ représente H, halogène; R?5¿ représente H, CN, halogène, alkyle C¿1?-C¿4?, haloalkyle C¿1?-C¿4?, alcoxy C¿1?-C¿4? ou bien haloalcoxy C¿1?-C¿4?; Z représente -N=C(XR?6¿)-O- ou bien -N=C(XR?6¿)-S-, lié à .alpha. par l'intermédiaire de l'azote, de l'oxygène ou du soufre; X représente une liaison chimique, oxygène, soufre, -S(O)-, -SO¿2?-, -NH- ou bien -N(R?7¿)-; R?6¿, R?7¿ représentent alkyle C¿1?-C¿6?, haloalkyle C¿1?-C¿6?, cyanoalkyle C¿1?-C¿4?, hydroxyalkyle C¿1?-C¿4?, alcényle C¿3?-C¿6?, cyanoalcényle C¿3?-C¿6?, haloalcényle C¿3?-C¿6?, alkinyle C¿3?-C¿6?, cyanoalkinyle C¿3?-C¿6?, haloalkinyle C¿3?-C¿6?, alcoxy C¿1?-C¿4?-alkyle C¿1?-C¿4?, haloalcoxy C¿1?-C¿4?-alkyle C¿1?-C¿4?, alcényloxy C¿3?-C¿4?-alkyle C¿1?-C¿4?, alkinyloxy C¿3?-C¿4?-alkyl C¿1?-C¿4?, cycloalkyloxy C¿3?-C¿8?-alkyle C¿1?-C¿4?, aminoalkyle C¿1?-C¿4?, alkylamino C¿1?-C¿4?-alkyle C¿1?-C¿4?, di(alkyle C¿1?-C¿4?)aminoalkyle C¿1?-C¿4?, alkyle C¿1?-C¿4?-thioalkyle C¿1?-C¿4?, haloalkyle C¿1?-C¿4?-thioalkyl C¿1?-C¿4?, alcényle C¿3?-C¿4?-thioalkyle C¿1?-C¿4?, alkinyle C¿3?-C¿4?-thioalkyle C¿1?-C¿4?, alkyle C¿1?-C¿4?-sulfinylalkyle C¿1?-C¿4?, haloalkyle C¿1?-C¿4?-sulfinylalkyle C¿1?-C¿4?, alcényl C¿3?-C¿4?-sulfinylealkyle C¿1?-C¿4?, alkinyle C¿3?-C¿4?-sulphinylalkyle C¿1?-C¿4?, alkyle C¿1?-C¿4? sulfonyl-C¿1?-C¿4?, haloalkyle C¿1?-C¿4?-sulfonylalkyle C¿1?-C¿4?, alcényle C¿3?-C¿4?-sulfonylalkyle C¿1?-C¿4?, alkinyle C¿3?-C¿4?-sulfonylalkyle C¿1?-C¿4?, hydroxycarbonylalkyle C¿1?-C¿4?, alcoxy C¿1?-C¿4?-carbonylalkyle C¿1?-C¿4?, qui peut porter un groupe CN ou alcoxy C¿1?-C¿4?-carbonyle, alkyle C¿1?-C¿4?-thiocarbonylalkyle C¿1?-C¿4?, aminocarbonylalkyle C¿1?-C¿4?, alkyle C¿1?-C¿4?-aminocarbonylalkyle C¿1?-C¿4?, di(alkyl C¿1?-C¿4?)aminocarbonylalkyle C¿1?-C¿4?, di(alkyle C¿1?-C¿4?) phosphonylalkyle C¿1?-C¿4?, alcoxy C¿1?-C¿4?-iminoalkyle C¿1?-C¿4?, alcényle C¿3?-C¿4?-oxyiminoalkyle C¿1?-C¿4?, cycloalkyle C¿3?-C¿8? éventuellement substitué, cycloalkyle C¿3?-C¿8?-alkyle C¿1?-C¿4?, phényle, phénylalkyle C¿1?-C¿4?, hétérocyclyle ou hétérocyclylalkyle C¿1?-C¿4? possédant trois à sept éléments, chaque noyau cycloalkyle ou hétérocyclyle pouvant contenir un élément CO ou bien CS; si X représente une liaison chimique, -O-, -S-, -NH- ou bien -N(R?7¿)-, R?6¿ représentant également alkyle C¿1?-C¿4?-carbonyle, haloalkyle C¿1?-C¿4?-carbonyle, alcoxy C¿1?-C¿4?-carbonyle, alkyle C¿1?-C¿4?-sulfonyle ou bien haloalkyle C¿1?-C¿4?-sulfonyle; si X représente une liaison chimique, R?6¿ représentant en outre CN, SH, NH¿2?, halogène, -CH¿2?-CH(halogène)-R?8¿, -CH=CH-R?8¿ ou bien -CH=C(halogène)-R?8¿, où R?8¿ représente COOH, alcoxy C¿1?-C¿4?-carbonyle, alkyle C¿1?-C¿4?-thiocarbonyle, CONH¿2?, alkyle C¿1?-C¿4?-aminocarbonyle, ?E?alkyl C¿1?-C¿4?)aminocarbonyle ou bien di(alkyl C¿1?-C¿4?)phosphonyle; ou bien R?6¿ + R?7¿ représentent une chaîne, éventuellement substituée, 1,3-propylène, tétraméthylène, pentaméthylène ou éthylènoxyéthylène. Ces composés peuvent être utilisés comme herbicides et pour le dessèchement et la défoliation de plantes.

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