Substituted Oxadiazoles for Combating Phytopathogenic Fungi

A compound of formula I, or an N-oxide, or an agriculturally acceptable salt thereof,

• wherein:
• RA is independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• n is 0, 1 or 2;
• R1 is a bicyclic carbocycle of the formula Ra
• wherein
• Ca and Cb are bridgehead carbon atoms;
• X is a direct single bond or a divalent group selected from the group consisting of —CH2—, —CH2—CH2—, —(CH2)3—, —(CH2)4—, —CH═CH—, —CH2—CH═CH—, —CH═CH—CH2— and —CH═CH—CH═CH—;
• Y and Z independently of each other are a divalent group selected from the group consisting of —CH2—, —CH2—CH2—, —(CH2)3—, —(CH2)4—, —CH═CH—, —CH2—CH═CH—, —CH═CH—CH2— and —CH═CH—CH═CH—;
• or R1 is a tricyclic carbocycle of the formula Rb
• wherein
• Ca and Cb are bridgehead carbon atoms;
• X is a direct single bond or a divalent group selected from the group consisting of —CH2—, —CH2—CH2—, —(CH2)3—, —(CH2)4—, —CH═CH—, —CH2—CH═CH—, —CH═CH—CH2— and —CH═CH—CH═CH—;
• Y and Z independently of each other are a divalent group selected from the group consisting of —CH2—, —CH2—CH2—, —(CH2)3—, —(CH2)4—, —CH═CH—, —CH2—CH═CH—, —CH═CH—CH2— and —CH═CH—CH═CH—;
• and wherein groups Y and Z are attached to the bridgehead carbon atoms Ca and Cb;
• T is a divalent group selected from the group consisting of —CH2—, —CH2—CH2—, —(CH2)3—, —(CH2)4—, —CH═CH—, —CH2—CH═CH—, —CH═CH—CH2— and —CH═CH—CH═CH—;
• and wherein the group T is attached to one carbon atom in each of the groups Y and Z;
• and with the proviso that, if R1 is a tricyclic carbocycle of the formula Rb,
• wherein X is a direct single bond or a divalent group —CH2—, the groups T and Z independently of each other are a divalent group selected from the group consisting of —CH2—CH2—, —(CH2)3—, —(CH2)4—, —CH═CH—, —CH2—CH═CH—, —CH═CH—CH2— and —CH═CH—CH═CH—;
• and wherein the groups Ra or Rb are connected to the group W through one of the ring carbon atoms;
• and wherein R1 is unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible number of radicals selected from the group consisting of oxo, hydroxy, halogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, vinylidene and dichlorovinylidene;
• W is #1-(C═O)—NR2-#2, #1-NR2—(C═O)-#2, #1-(C═S)—NR2-#2, #1-NR2—(C═S)-#2, #1-S(═O)p—NR2-#2 or #1-NR2—S(═O)p-#2;
• wherein #1 denotes the position, which is attached to the group —CR3R4— or, if m is 0, to the phenyl group, and #2 denotes the position, which is attached to R1;
• p is 0, 1 or 2;
• R2 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, phenyl, C(═O)—(C1-C6-alkyl) or C(═O)—(C1-C6-alkoxy);
• and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, hydroxy, cyano, C1-C6-alkyl, C1-C6-alkoxy and C3-C8-cycloalkyl;
• m is 0 or 1;
• R3, R4 independently of each other are selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkenyl, C1-C4-alkynyl, C1-C4-haloalkyl and C1-C4-alkoxy;
• or R3 and R4 together with the carbon atom to which they are bound form a monocyclic 3- to 5-membered saturated heterocycle or saturated carbocycle;
• and wherein the saturated heterocycle includes beside one or more carbon atoms no heteroatoms or 1 or 2 heteroatoms independently selected from the group consisting of N, O and S as ring member atoms;
• and wherein the heterocycle or the carbocycle is unsubstituted or substituted 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano and C1-C2-alkyl;
• with the exception of compounds of the formula I, wherein
• m is 0;
• W is #1-NR2—(C═O)-#2, #1-NR2—(C═S)-#2 or #1-NR2—S(═O)p-#2, wherein the variables p and R2 are defined as above for compounds of the formula I;
• and
• R1 is a bicyclic carbocycle of the formula Ra.