Substituted Isoxazole Derivatives

A compound of the formula I

• wherein
• A is CH or N;
• D is selected from the group consisting of H, halogen and SRD, wherein
• RD is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl and CN;
• R1 is selected from the group consisting of hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio, and C1-C6-haloalkylthio;
• wherein the aliphatic and/or alicyclic moieties of R1 are not further substituted or carry one, two, three, four or five identical or different groups R1a;
• wherein
• each R1a is independently selected from the group consisting of halogen, OH, CN, nitro, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylthio, C1-C8-haloalkylthio, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl, C1-C8-alkylcarbonyl, C1-C8-alkoxycarbonyl, unsubstituted aryl, aryl, that is substituted by one, two, three, four or five independently selected R1b, unsubstituted saturated, partially unsaturated or aromatic heterocyclyl and saturated, partially unsaturated or aromatic heterocyclyl, that is substituted by one, two, three, four or five independently selected R1b;
• each R1b is independently selected from the group consisting of halogen, OH, CN, nitro, NH2, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy, C1-C3-alkylthio, C1-C3-haloalkylthio, C1-C3-alkylsulfinyl, C1-C3-haloalkylsulfinyl, C1-C3-alkylsulfonyl, C1-C3-haloalkylsulfonyl, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, C1-C4-alkylcarbonyl, C1-C4-alkylcarbonyloxy, C1-C4-alkoxycarbonyl, and C1-C4-alkylcarbonylamino;
• R2 is independently selected from the substituents as given for R1;
• or R1 and R2 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, ten-, eleven-, twelve-, thirteen- or fourteen-membered carbocycle, which may be monocyclic or polycyclic or spirocyclic, or saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, ten-, eleven-, twelve-, thirteen- or fourteen-membered heterocycle, which may be monocyclic or polycyclic or spirocyclic, wherein the heterocycle contains one, two, three or four heteroatoms selected from the group consisting of N, O and S, or wherein the heterocycle contains one of S═O and SO2 as ring members, and wherein the carbo- or heterocycle is unsubstituted or carries one, two, three, four or five substituents R12a independently selected from the group consisting of halogen, CN, NO2, OH, SH, NH2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylthio, C1-C8-haloalkylthio, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl, C1-C8-alkylcarbonyl, C1-C8-alkoxycarbonyl, phenyl and phenyl that is substituted by one, two, three, four or five independently selected R1b;
• and
• wherein one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from the group consisting of C═CH2, C(═O) and C(═S);
• R3 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, phenyl, phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl and phenyl-C2-C4-alkynyl;
• wherein the aliphatic moieties of R3 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R3a which independently of one another are selected from:
• R3a is selected from the group consisting of halogen, OH, CN, nitro, C1-C4-alkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and C1-C4-haloalkoxy;
• wherein the cycloalkyl and/or phenyl moieties of R3 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R3b which independently of one another are selected from:
• R3b is selected from the group consisting of halogen, OH, CN, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and C1-C4-haloalkoxy;
• n is 0, 1, 2, 3 or 4;
• each R4 is independently selected from the group consisting of halogen, CN, NO2, OH, SH, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, S(O)p(C1-C4-alkyl), C(═O)(C1-C4-alkyl), C(═O)(OH), C(═O)(O—C1-C4-alkyl), C(═O)(NH(C1-C4-alkyl)), C(═O)(N(C1-C4-alkyl)2), C(═O)(NH(C3-C6-cycloalkyl)) and C(═O)—(N(C3-C6-cycloalkyl)2);
• wherein each of R4 is unsubstituted or further substituted by one, two, three or four R4a;
• wherein
• each R4a is independently selected from the group consisting of halogen, CN, NO2, OH, C1-C4-alkyl, C1-C4-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
• Y is a divalent group selected from the group consisting of —O—, —S—, SO—, —SO2—, —NH—, —N(C1-C4-alkyl)-, CR6R7—, —CR8R9—CR10R11—, —CR12═CR13 and —C≡C—;
• wherein
• R6, R7, R8, R9, R10, R11, R12, R13 are independently selected from the group consisting of hydrogen, halogen, CN, nitro, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
• Z is phenyl or five or six-membered heteroaryl, wherein the heteroaryl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, wherein the phenyl and the heteroaryl is unsubstituted (m=0) or substituted by (R5)m;
• wherein
• m is 0, 1, 2, 3, 4 or 5;
• and
• each R5 is independently selected from the group consisting of halogen, CN, NO2, OH, SH, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, S(O)p(C1-C4-alkyl), C(═O)(C1-C4-alkyl), C(═O)(OH), C(═O)(O—C1-C4-alkyl), C(═O)(NH(C1-C4-alkyl)), C(═O)(N(C1-C4-alkyl)2), C(═O)(NH(C3-C6-cycloalkyl)) and C(═O)—(N(C3-C6-cycloalkyl)2);
• wherein each of R5 is unsubstituted or further substituted by one, two, three or four R5a
• wherein
• each R5a is independently selected from the group consisting of halogen, CN, NO2, OH, C1-C4-alkyl, C1-C4-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
• p is 0, 1 or 2;
• and the N-oxides and the agriculturally acceptable salts thereof.