Phenylimino-thiadiazabicycloalkane derivatives, processes...

C - Chemistry – Metallurgy – 07 – D

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C07D 513/04 (2006.01) A01N 43/90 (2006.01) C07C 205/58 (2006.01) C07C 229/60 (2006.01) C07C 235/06 (2006.01) C07C 235/08 (2006.01) C07C 251/66 (2006.01) C07C 259/06 (2006.01) C07C 323/12 (2006.01) C07C 327/28 (2006.01) C07C 331/26 (2006.01) C07C 331/28 (2006.01) C07D 231/04 (2006.01) C07D 237/04 (2006.01) C07D 243/02 (2006.01) C07D 295/088 (2006.01) C07D 401/12 (2006.01) C07D 403/12 (2006.01) C07D 405/12 (2006.01) C07D 409/12 (2006.01) C07D 417/12 (2006.01)

Patent

CA 2181583

Compounds of formula (I): wherein R is C1-C6alkyl, C1-C6haloalkyl, C3- C6alkenyl, C3-C6alkynyl, C1-C4alkoxy or C3-C6cycloalkyl; R1 is halogen; R2 and R3 are each independently of the other C1-C4alkyl; R4 is halogen or a group of the formula -X-R5, -X-A-R6 or (a); R5 is hydrogen, C1-C6alkyl, C1-C8haloalkyl, C1-C4alkoxy-C1-C4alkyl, C1-C10alkylthio-C1-C4alkyl, C1-C4alkylamino-C1- C4alkyl, di-C1-C4alkylamino-C1-C4alkyl, cyano-C1-C8-alkyl, C3-C8alkenyl, C3- C8haloalkenyl, C3-C8alkynyl, C3-C6cycloalkyl, oxetanyl, C3-C7-halocycloalkyl, C3-C7cycloalkyl-C1-C4alkyl, phenyl-C1-C3alkyl that is unsubstituted or substituted in the phenyl ring by 1, 2 or 3 identical or different substituents selected from halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy and C1-C4haloalkoxy, or R5 is an alkali metal, alkaline earth metal or ammonium ion, or is the group -N=C(CH3)2, -CH2-O-N=C(CH3)2 or -CH2CH2-O- N=C(CH3)2; X is oxygen or sulfur; A is C1-C4 alkylene; R6 is a 5- or 6- membered heterocyclic ring that contains from 1 to 3 hetero atoms selected from the group oxygen, nitrogen and sulfur and that is bonded via the carbon or nitrogen atom to the alkylene chain A, it being possible for the heterocyclic ring in turn also to be benzene-fused and mono- or di-substituted by halogen, C1-C4alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, di-C1- C3alkylamino, hydroxy or by an oxy function; R7 is hydrogen, C1-C6alkyl, C1- C4haloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C3-C6alkenyl, C3-C6alkynyl, C3-C8cycloalkyl, hydroxy-C1-C4alkyl or cyano-C1-C4alkyl; R8 is hydrogen, C1- C6alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkyl, C3- C6alkenyl, phenyl or phenyl-C1-C3alkyl, the phenyl ring being unsubstituted or mono-, di- or tri-substituted by halogen, C1-C4alkyl, C1-C4haloalkyl, C1- C4alkoxy or by C1-C4haloalkoxy; or R7 and R8, together with the nitrogen atom to which they are bonded, form a pyrrolidino, piperidino, morpholino, thiomorpholino or piperazino ring that is unsubstituted or mono- or di- substituted by C1-C3alkyl; Z is oxygen or sulfur; n is 3, 4 or 5; and n1 is 0, 1, 2 or 3, and salts of those compounds, are suitable as herbicides for controlling weeds in crops of useful plants.

Composés de la formule (I), dans laquelle R représente C¿1?-C¿6?alkyle, C¿1?-C¿6?haloalkyle,C¿3?-C¿6?alcényle, C¿3?-C¿6?alcynyle, C¿1?-C¿4?alcoxy ou C¿3?-C¿6?cycloalkyle; R¿1? représente halogène; R¿2? et R¿3? représentent chacun indépendamment C¿1?-C¿4?alkyle; R¿4? représente halogène ou un groupe de la formule -X-R¿5?, -X-A-R¿6? ou (a); R¿5? représente hydrogène, C¿1?-C¿6?alkyle, C¿1?-C¿8?haloalkyle, C¿1?-C¿4?alcoxy-C¿1?-C¿4?alkyle, C¿1?-C¿10?alkylthio-C¿1?-C¿4?alkyle, C¿1?-C¿4?alkylamino-C¿1?-C¿4?alkyle, di-C¿1?-C¿4?alkylamino-C¿1?-C¿4?alkyle, cyano-C¿1?-C¿8?alkyle, C¿3?-C¿8?alcényle, C¿3?-C¿8?haloalcényle, C¿3?-C¿8?alcynyle, C¿3?-C¿6?cycloalkyle, oxétanyle, C¿3?-C¿7?halocycloalkyle, C¿3?-C¿7?cycloalkyl-C¿1?-C¿4?alkyle, phényle-C¿1?-C¿3?alkyle non substitué ou substitué dans le cycle phényle par 1, 2 ou 3 substituants identiques ou différents choisis entre halogène, C¿1?-C¿4?alkyle, C¿1?-C¿4?haloalkyle, C¿1?-C¿4?alcoxy et C¿1?-C¿4?haloalcoxy, ou R¿5? représente un métal alcalin, un métal alcalino-terreux ou un ion ammonium, ou représente le groupe -N=C(CH¿3?)¿2?, -CH¿2?-O-N=C(CH¿3?)¿2?, ou -CH¿2?CH¿2?-O-N=C(CH¿3?)¿2?; X représente oxygène ou soufre; A représente C¿1?-C¿4?alkylène; R¿6? représente un hétérocycle à 5 ou 6 éléments contenant de 1 à 3 hétéroatomes choisi entre oxygène, azote et soufre, et lié par l'atome de carbone ou d'azote à la chaîne alkylène A, cet hétérocycle pouvant à son tour être fusionné par benzène et mono- ou bisubstitué par halogène, C¿1?-C¿4?alkyle, C¿1?-C¿3?haloalkyle, C¿1?-C¿3?alcoxy et C¿1?-C¿3?haloalcoxy, di-C¿1?-C¿3?alkylamino, hydroxy ou par une fonction hydroxy; R¿7? représente hydrogène, C¿1?-C¿6?alkyle, C¿1?-C¿4?haloalkyle, C¿1?-C¿4?alcoxy, C¿1?-C¿4?alcoxy-C¿1?-C¿4?alkyle, C¿3?-C¿6?alcényle, C¿3?-C¿6?alcynyle, C¿3?-C¿8?cycloalkyle, hydroxy-C¿1?-C¿4?alkyle ou cyano-C¿1?-C¿4?alkyle; R¿8? représente hydrogène, C¿1?-C¿6?alkyle, C¿1?-C¿4?haloalkyle, C¿1?-C¿4?alcoxy-C¿1?-C¿4?alkyle, hydroxy-C¿1?-C¿4?alkyle, C¿3?-C¿6?alcényle, phényle ou phényl-C¿1?-C¿3?alkyle, le cycle phényle n'étant pas substitué ou étant mono-, bi- ou trisubstitué par halogène, C¿1?-C¿4?alkyle, C¿1?-C¿4?haloalkyle, C¿1?-C¿4?alcoxy, ou par C¿1?-C¿4?haloalcoxy; ou R¿7? et R¿8? forment avec l'atome d'azote auquel ils sont liés un cycle pyrrolidino, pipéridino, morpholino, thiomorphilno, ou pipérazino non substitué, ou mono- ou bisubstitué par C¿1?-C¿3?alkyle; Z représente oxygène ou soufre; n vaut 3, 4 ou 5; et n¿1? vaut 0, 1, 2 ou 3. Ces composés, ainsi que leurs sels, sont aptes à être utilisés comme herbicides pour lutter contre les mauvaises herbes dans des cultures de plantes utiles.

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