N-sulphonyl and n-sulphinyl amino acid amides as microbiocides

C - Chemistry – Metallurgy – 07 – C

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C07C 311/01 (2006.01) A01N 41/06 (2006.01) A01N 43/34 (2006.01) C07C 307/06 (2006.01) C07C 311/06 (2006.01) C07C 311/07 (2006.01) C07C 311/11 (2006.01) C07C 311/14 (2006.01) C07C 311/24 (2006.01) C07C 313/06 (2006.01) C07C 313/20 (2006.01) C07C 317/04 (2006.01) C07C 323/60 (2006.01) C07C 323/67 (2006.01) C07D 295/26 (2006.01)

Patent

CA 2186510

.alpha.-amino acid amides of formula (I), in which n is the number zero or one; R1 is C1-C12alkyl, which is unsubstituted or can be substituted by C1- C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C3-C8cycloalkyl, cyano, C1- C6alkoxycarbonyl, C3-C6alkenyloxycarbonyl or C3-C6alkynyloxycarbonyl; C3- C8cycloalkyl; C2-C12alkenyl; C2-C12 alkynyl; C1-C12halogenoalkyl or a group NR13R14; in which R13 and R14 independently of one another are hydrogen or C1- C6alkyl or together are tetra- or pentamethylene; R2 and R3 independently of one another are hydrogen; C1-C8alkyl; C1-C8alkyl which is substituted by hydroxyl, C1-C4alkoxy, mercapto or C1-C4alkylthio; C3-C8alkenyl; C3-C8alkynyl; C3-C8cycloalkyl or C3-C8cycloalkyl-C1-C4alkyl, or in which the two groups R2 and R3, together with the carbon atom to which they are bonded, form a three- to eight-membered carbocyclic ring; R4 is hydrogen or C1-C6alkyl; R5 is hydrogen; C1-C6alkyl or phenyl, which is unsubstituted or can be substituted by halogen, nitro, C1-C4alkyl, C1-C4halogenoalkyl, C1-C4alkoxy or C1- C4alkylthio; and R6 is a group G, in which R7 and R8 independently of one another are hydrogen or C1-C6alkyl; p is the number zero or one; and R9, R10 and R11 independently of one another are hydrogen, C1-C6alkyl, C1- C6halogenoalkyl, C3-C6alkenyl, C3-C6alkynyl, C1-C6alkoxy, C3-C6alkenyloxy, C3- C6alkynyloxy, C1-C6alkylthio, halogen or nitro are valuable microbicides. They can be employed in crop protection in the form of suitable compositions, for example for controlling fungal diseases.

Des amides d'acides aminés .alpha. de la formule (I) sont des microbicides précieux. Dans cette formule, n vaut zéro ou un; R¿1? représente alcoyle C¿1?-C¿12? qui est non substitué ou peut être substitué par alcoxy C¿1?-C¿4?, alcoylthio C¿1?-C¿4?, alcoylsulfonyle C¿1?-C¿4?, cycloalcoyle C¿3?-C¿8?, cyano, alcoxycarbonyle C¿1?-C¿6?, alcényloxycarbonyle C¿3?-C¿6? ou alcynyloxycarbonyle C¿3?-C¿6?; cycloalcoyle C¿3?-C¿8?; alcényle C¿2?C¿12?; alcynyle C¿2?-C¿12?; halogénoalcoyle C¿1?-C¿12? ou un groupe NR¿13?R¿14?, dans lequel R¿13? et R¿14? représentent indépendamment hydrogène ou alcoyle C¿1?-C¿6? ou ils représentent ensemble tétra- ou pentaméthylène; R¿2? et R¿3? représentent indépendamment hydrogène, alcoyle C¿1?-C¿8?, alcoyle C¿1?-C¿8? substitué par hydroxyle, alcoxy C¿1?-C¿4?, mercapto ou alcoylthio C¿1?-C¿4?; alcényle C¿3?-C¿8?; alcynyle C¿3?-C¿8?; cycloalcoyle C¿3?-C¿8? ou cycloalcoyle C¿3?-C¿8? alcoyle C¿1?-C¿4?; ou bien les deux groupes R¿2? et R¿3?, ensemble avec l'atome de carbone auquel ils sont liés, forment un cycle carbocyclique possédant de 3 à 8 chaînons; R¿4? représente hydrogène, alcoyle C¿1?-C¿6?; R¿5? représente hydrogène; alcoyle C¿1?-C¿6? ou phényle, qui est non substitué ou peut être substitué par halogène, nitro, alcoyle C¿1?-C¿4?, halogénoalcoyle C¿1?-C¿4?, ou alcoxy C¿1?-C¿4? ou alcoylthio C¿1?-C¿4?; et R¿6? représente un groupe (G) dans lequel R¿7? et R¿8? représente indépendamment hydrogène ou alcoyle C¿1?-C¿6?; p vaut zéro ou un; et R¿9?, R¿10? et R¿11? représentent indépendamment hydrogène, alcoyle C¿1?-C¿6?, halogénoalcoyle C¿1?-C¿6?, alcényle C¿3?-C¿6?, alcynyle C¿3?-C¿6?, alcoxy C¿1?-C¿6?, alcényloxy C¿3?-C¿6?, alcynyloxy C¿3?-C¿6?, alcoylthio C¿1?-C¿6?, halogène ou nitro. On peut utiliser ces amides dans la protection des récoltes sous la forme de compositions appropriées, par exemple, à la lutte contre les maladies fongiques.

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