US2022169621A1PendingUtilityA1
Oxadiazoles for use in controlling phytopathogenic fungi
Est. expiryJan 30, 2038(~11.5 yrs left)· nominal 20-yr term from priority
Inventors:Paras Raybhan BhujadeRajesh PawarMaruti N. NaikRajender Kumar PotlapallyNitin Ramesh TembhareSantosh Shridhar AutkarRuchi GargHagalavadi M. VenkateshaAlexander KlausenerVisannagari RamakrishnaNilesh Bharat AdhavPooja Trivedi
C07D 417/04A01N 43/82C07D 271/06C07D 417/12C07D 413/12C07D 413/04
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Claims
Abstract
The present invention relates to novel oxadiazoles of Formula I. wherein, R 1 , L 1 , A, L 2 and R 10 are as defined in the detailed description.
Claims
exact text as granted — not AI-modified1 - 13 . (canceled)
14 . A compound of Formula Ia;
wherein L 1 is a direct bond;
A is phenyl;
L 2 is a fragment selected from the group of
wherein, k is an integer ranging from 0 to 4; an expression “#” indicates the point of attachment;
R 7 and R 8 are independently selected from hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; or
R 7 and R 8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -alkoxy;
R 9 is selected from the group consisting of hydrogen; NR g R h , wherein, R g and R h independently represent hydrogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 3 -C 8 -cycloalkyl; (C═O)—R i , wherein, R i represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -haloalkoxy; C 1-8 -alkyl-S(O) 0-2 R j , wherein R j represents hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl; C 1 -C 6 -alkyl-(C═O)—R i , CR i ═NR g , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 4 -C 8 -cycloalkenyl, C 5 -C 8 -cycloalkynyl, C 7 -C 19 -aralkyl:
wherein, R g may optionally be substituted with one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl and di-C 1 -C 6 -alkylaminocarbonyl;
R 10 is selected from the group consisting of halogen, hydroxy, cyano, —OR 12 , —NR 13 R 14 , nitro, —SH, —SCN, —COR 15 , —C(═O)OR 12 , —C(═O)NR 13 R 14 , —NR 13 C(═O)R 15 , —O(C═O)R 15 , —O(C═O)NR 13 R 14 , —C(═NOR 13 )R 15 , —NR 13 SO 2 R 16 , —CSR 16 , —C(═S)OR 12 , —C(═S)NR 13 R 14 , —NR 13 C(═S)R 15 , —O(C═S)R 15 , —O(C═S)NR 13 R 14 , —O(C═S)SR 16 , —N═C(R 15 ) 2 , —NHCN, —SO 2 NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO 2 NR 12 R 13 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -thioalkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylamino-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkylamino, C 3 -C 8 -cycloalkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -hydroxyalkenyl, C 2 -C 6 -hydroxyalkynyl, C 3 -C 8 -halocycloalkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfinyl, tri-C 1 -C 6 -alkylsilyl, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, C 1 -C 6 -alkylcarbonylthio, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylsulfinyloxy, C 6 -C 10 -arylsulfonyloxy, C 6 -C 10 -arylsulfinyloxy, C 6 -C 10 -arylsulfonyl, C 6 -C 10 -arylsulfinyl, C 6 -C 10 -arylthio, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenylcarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylthio, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy, C 2 -C 6 -haloalkenylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkynyl, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -haloalkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxycarbonylamino, di(C 1 -C 6 -haloalkylamino-C 1 -C 6 -alkyl, C 3 -C 8 -halocycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -haloalkylsulfonylaminocarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, C 1 -C 6 -alkoxycarbonylalkoxy, C 1 -C 6 -alkylaminothiocarbonylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthiocarbonyl, C 3 -C 8 -cycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxycarbonyl, di-C 1 -C 6 -alkylaminothiocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkoxy, C 3 -C 8 -halocycloalkoxy-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 -alkylthiocarbonyloxy, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkylsulfonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkyl, di(C 1 -C 6 -haloalkyl)amino, di-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyloxy, tri-C 1 -C 6 -alkylsilyloxy, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyl, cyano(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxysulfonyl, C 3 -C 8 -halocycloalkoxycarbonyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, C 1 -C 6 -cyanoalkoxycarbonyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkynylcarbonyloxy, C 2 -C 6 -haloalkynylcarbonyloxy, cyanocarbonyloxy, C 1 -C 6 -cyanoalkylcarbonyloxy, C 3 -C 8 -cycloalkylsulphonyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylsulphonyloxy, C 3 -C 8 -halocycloalkylsulphonyloxy, C 2 -C 6 -alkenylsulphonyloxy, C 2 -C 6 -alkynylsulphonyloxy, C 1 -C 6 -cyanoalkylsulphonyloxy, C 2 -C 6 -haloalkenylsulphonyloxy, C 2 -C 6 -haloalkynylsulphonyloxy, C 2 -C 6 -alkynylcycloalkyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -cyanoalkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 2 -C 6 -alkenyloxycarbonyloxy, C 2 -C 6 -alkynyloxycarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyloxy, sulfilimines, sulfoximines, SF 5 and Z 1 Q 1 ;
Z 1 and Z 2 are independently a direct bond, CR 2d R 3d , N, O, C(O), C(S), C(═CR 2d R 3d ) or S(O) 0-2 ;
Q 1 and Q 2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R 17 ; or
Q 1 and Q 2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15-membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O) 0-2 , and C ring member of the non-aromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(═CR 2c R 3c ) or C(═NR 6b ), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R 17 ;
wherein, R 17 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, —OR 12 , —NR 13 R 14 , nitro, —SH, —SCN, —COR 15 , —C(═O)OR 12 , —C(═O)NR 13 R 14 , —NR 13 C(═O)R 15 , —O(C═O)R 15 , —O(C═O)NR 13 R 14 , —C(═NOR 13 )R 15 , —NR 13 SO 2 R 16 , -CSR 16 , —C(═S)OR 12 , —C(═S)NR 13 R 14 , —NR 13 C(═S)R 5 , —O(C═S)R 15 , —O(C═S)NR 13 R 14 , —O(C═S)SR 16 , —N═C(R 15 ) 2 , —NHCN, —SO 2 NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO 2 NR 12 R 13 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -thioalkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylamino-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkylamino, C 3 -C 8 -cycloalkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -hydroxyalkenyl, C 2 -C 6 -hydroxyalkynyl, C 3 -C 8 -halocycloalkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfinyl, tri-C 1 -C 6 -alkylsilyl, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, C 1 -C 6 -alkylcarbonylthio, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylsulfinyloxy, C 6 -C 1 -arylsulfonyloxy, C 6 -C 10 -arylsulfinyloxy, C 6 -C 10 -arylsulfonyl, C 6 -C 10 -arylsulfinyl, C 6 -C 10 -arylthio, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenylcarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylthio, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy, C 2 -C 6 -haloalkenylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkynyl, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -haloalkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxycarbonylamino, di(C 1 -C 6 -haloalkyl)amino-C 1 -C 6 -alkyl, C 3 -C 8 -halocycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -haloalkylsulfonylaminocarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, C 1 -C 6 -alkoxycarbonylalkoxy, C 1 -C 6 -alkylaminothiocarbonylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthiocarbonyl, C 3 -C 8 -cycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxycarbonyl, di-C 1 -C 6 -alkylaminothiocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkoxy, C 3 -C 8 -halocycloalkoxy-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 -alkylthiocarbonyloxy, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkylsulfonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkyl, di(C 1 -C 6 -haloalkyl)amino, di-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyloxy, tri-C 1 -C 6 -alkylsilyloxy, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyl, cyano(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxysulfonyl, C 3 -C 8 -halocycloalkoxycarbonyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, C 1 -C 6 -cyanoalkoxycarbonyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkynylcarbonyloxy, C 2 -C 6 -haloalkynylcarbonyloxy, cyanocarbonyloxy, C 1 -C 6 -cyanoalkylcarbonyloxy, C 3 -C 8 -cycloalkylsulphonyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylsulphonyloxy, C 3 -C 8 -halocycloalkylsulphonyloxy, C 2 -C 6 -alkenylsulphonyloxy, C 2 -C 6 -alkynylsulphonyloxy, C 1 -C 6 -cyanoalkylsulphonyloxy, C 2 -C 6 -haloalkenylsulphonyloxy, C 2 -C 6 -haloalkynylsulphonyloxy, C 2 -C 6 -alkynylcycloalkyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -cyanoalkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 2 -C 6 -alkenyloxycarbonyloxy, C 2 -C 6 -alkynyloxycarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyloxy, sulfilimines, sulfoximines, SF 5 and Z 2 Q 2 ;
R 9 and R 10 ; and or R 9 and R A together with the atoms to which they are attached may form a 3- to 10-membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R 17 ;
wherein,
R 12 is selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 13 and R 14 are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 15 is selected from the group consisting of hydrogen, hydroxy, halogen, NR b R c , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -cycloalkyl, and
R 16 is selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 8 -cycloalkyl;
or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof.
15 . The compound of claim 14 , wherein L 2 is the fragment of formula L 2a .
16 . The compound of claim 14 , wherein L 2 is the fragment of formula L 2b .
17 . A compound of Formula Ib;
L 1 is a direct bond, —CR 2 R 3 —, —C(═O)—, —O—, —S(═O) 0-2 —, —NR 4 — or —CR 2 R 3 C(═O)—, wherein, an expression “-” at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A;
A is an aromatic or non-aromatic 5- or 6-membered carbocyclic ring, wherein the ring members of the non-aromatic carbocyclic ring are selected from C, C(═O), C(═S), C(═CR 2a R 3a ) and C═NR 6 ; or
A is an aromatic or non-aromatic 5- or 6-membered heterocyclic ring; wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(═O) 0-2 , and S(═O) 0-1 (═NR 6 ) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(═O), C(═S), C(═CR 2a R 3a ) and C═NR 6 ; and
wherein, A is unsubstituted or is substituted with one or more identical or different R A groups,
wherein, R A is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, SF 5 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio and C 1 -C 6 -haloalkylsulfinyl;
wherein, R A may be optionally substituted with one or more identical or different R a selected from halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy;
or
two R A together with the atoms to which they are attached may form a 3- to 10-membered aromatic or non-aromatic carbocyclic ring or ring system, or aromatic or non-aromatic heterocyclic ring or ring system which may be optionally substituted with one or more identical or different R a ,
R 4 , R 6 , R 6a , R 6b , and R 6c are independently selected from the group of hydrogen, cyano, hydroxy, NR b R c , (C═O)—R d , S(O) 0-2 R e , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylamino and C 3 -C 8 -cycloalkyl;
R b and R c are independently selected from the group of hydrogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl or C 3 -C 8 -halocycloalkyl,
R d is selected from the group of hydrogen, hydroxy, halogen, NR b R c , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl; and
R e is selected from the group of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl;
L 2 is a fragment selected from the group of
wherein, k is an integer ranging from 0 to 4; an expression “#” indicates the point of attachment;
wherein, in Formula I when R 1 is CF 3 ; A is phenyl ring or C 3 -C 7 carbocyclic ring or 5- to 6-membered heterocyclic ring; L 2 is L 2 a wherein S atom of L 2 a is attached to A, and k=0 then R 10 is not hydrogen, cyano, nitro, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
wherein, in Formula I when R 1 is CF 3 ; A is phenyl ring or 5- to 6-membered heteroaromatic ring L 2 is L 2b wherein S atom of L 2b is attached to A, and k=0 to 4 then R 10 is not cyano, nitro, R 11 and OR 11 ; wherein, R 11 is hydrogen, C 1 -C 6 -alkyl optionally substituted with a group selected from halogen, cyano, nitro, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, and phenyl ring optionally substituted with C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy;
R 2 , R 3 , R 2a , R 3a , R 2b , R 3b , R 2c , R 3c , R 2d , R 3d , R 2e , R 3e , R 7 and R 8 are independently selected from hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; or
R 2 and R 3 ; R 2a and R 3a ; R 2b and R 3b ; R 2c and R 3c ; R 2d and R 3d ; R 2e and R 3e ; and or R 7 and R 8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -alkoxy;
R 9 is selected from the group consisting of hydrogen; NR g R h , wherein, R g and R h independently represent hydrogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 3 -C 8 -cycloalkyl; (C═O)—R i , wherein, R i represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -haloalkoxy; C 1-8 -alkyl-S(O) 0-2 R j , wherein R j represents hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl; C 1 -C 6 -alkyl-(C═O)—R i , CR i ═NR g , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 4 -C 8 -cycloalkenyl, C 5 -C 8 -cycloalkynyl, C 7 -C 19 -aralkyl;
wherein, R 9 may optionally be substituted with one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl and di-C 1 -C 6 -alkylaminocarbonyl;
R 10 is selected from the group consisting of halogen, hydroxy, cyano, —OR 12 , —NR 13 R 14 , nitro, —SH, —SCN, —COR 15 , —C(═O)OR 12 , —C(═O)NR 13 R 14 , —NR 13 C(═O)R 15 , —O(C═O)R 15 , —O(C═O)NR 13 R 14 , —C(═NOR 13 )R 15 , —NR 13 SO 2 R 16 , —CSR 16 , —C(═S)OR 12 , —C(═S)NR 13 R 14 , —NR 13 C(═S)R 15 , —O(C═S)R 15 , —O(C═S)NR 13 R 14 , —O(C═S)SR 16 , —N═C(R 15 ) 2 , —NHCN, —SO 2 NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO 2 NR 12 R 13 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -thioalkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylamino-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkylamino, C 3 -C 8 -cycloalkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -hydroxyalkenyl, C 2 -C 6 -hydroxyalkynyl, C 3 -C 8 -halocycloalkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfinyl, tri-C 1 -C 6 -alkylsilyl, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, C 1 -C 6 -alkylcarbonylthio, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylsulfinyloxy, C 6 -C 10 -arylsulfonyloxy, C 6 -C 10 -arylsulfinyloxy, C 6 -C 10 -arylsulfonyl, C 6 -C 10 -arylsulfinyl, C 6 -C 10 -arylthio, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenylcarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylthio, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy, C 2 -C 6 -haloalkenylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkynyl, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -haloalkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxycarbonylamino, di(C 1 -C 6 -haloalkyl)amino-C 1 -C 6 -alkyl, C 3 -C 8 -halocycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -haloalkylsulfonylaminocarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, C 1 -C 6 -alkoxycarbonylalkoxy, C 1 -C 6 -alkylaminothiocarbonylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthiocarbonyl, C 3 -C 8 -cycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxycarbonyl, di-C 1 -C 6 -alkylaminothiocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkoxy, C 3 -C 8 -halocycloalkoxy-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 -alkylthiocarbonyloxy, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkylsulfonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkyl, di(C 1 -C 6 -haloalkyl)amino, di-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyloxy, tri-C 1 -C 6 -alkylsilyloxy, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyl, cyano(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxysulfonyl, C 3 -C 8 -halocycloalkoxycarbonyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, C 1 -C 6 -cyanoalkoxycarbonyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkynylcarbonyloxy, C 2 -C 6 -haloalkynylcarbonyloxy, cyanocarbonyloxy, C 1 -C 6 -cyanoalkylcarbonyloxy, C 3 -C 8 -cycloalkylsulphonyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylsulphonyloxy, C 3 -C 8 -halocycloalkylsulphonyloxy, C 2 -C 6 -alkenylsulphonyloxy, C 2 -C 6 -alkynylsulphonyloxy, C 1 -C 6 -cyanoalkylsulphonyloxy, C 2 -C 6 -haloalkenylsulphonyloxy, C 2 -C 6 -haloalkynylsulphonyloxy, C 2 -C 6 -alkynylcycloalkyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -cyanoalkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 2 -C 6 -alkenyloxycarbonyloxy, C 2 -C 6 -alkynyloxycarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyloxy, sulfilimines, sulfoximines, SF 5 and Z 1 Q 1 ;
Z 1 and Z 2 are independently a direct bond, CR 2d R 3d , N, O, C(O), C(S), C(═CR 2d R 3d ) or S(O) 0-2 ;
Q 1 and Q 2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R 17 ; or
Q 1 and Q 2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15-membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O) 0-2 , and C ring member of the non-aromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(═CR 2c R 3c ) or C(═NR 6b ), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R 17 ;
wherein, R 17 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, —OR 12 , —NR 13 R 14 , nitro, —SH, —SCN, —COR 15 , —C(═O)OR 12 , —C(═O)NR 13 R 14 , —NR 13 C(═O)R 15 , —O(C═O)R 15 , —O(C═O)NR 13 R 14 , —C(═NOR 13 )R 15 , —NR 13 SO 2 R 16 , —CSR 16 , —C(═S)OR 12 , —C(═S)NR 13 R 14 , —NR 13 C(═S)R 15 , —O(C═S)R 15 , —O(C═S)NR 13 R 14 , —O(C═S)SR 16 , —N═C(R 15 ) 2 , —NHCN, —SO 2 NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO 2 NR 12 R 13 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -thioalkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylamino-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkylamino, C 3 -C 8 -cycloalkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -hydroxyalkenyl, C 2 -C 6 -hydroxyalkynyl, C 3 -C 8 -halocycloalkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfinyl, tri-C 1 -C 6 -alkylsilyl, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, C 1 -C 6 -alkylcarbonylthio, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylsulfinyloxy, C 6 -C 10 -arylsulfonyloxy, C 6 -C 10 -arylsulfinyloxy, C 6 -C 10 -arylsulfonyl, C 6 -C 10 -arylsulfinyl, C 6 -C 10 -arylthio, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenylcarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylthio, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy, C 2 -C 6 -haloalkenylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkynyl, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -haloalkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxycarbonylamino, di(C 1 -C 6 -haloalkyl)amino-C 1 -C 6 -alkyl, C 3 -C 8 -halocycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -haloalkylsulfonylaminocarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, C 1 -C 6 -alkoxycarbonylalkoxy, C 1 -C 6 -alkylaminothiocarbonylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthiocarbonyl, C 3 -C 8 -cycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxycarbonyl, di-C 1 -C 6 -alkylaminothiocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkoxy, C 3 -C 8 -halocycloalkoxy-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 -alkylthiocarbonyloxy, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkylsulfonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkyl, di(C 1 -C 6 -haloalkyl)amino, di-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyloxy, tri-C 1 -C 6 -alkylsilyloxy, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyl, cyano(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxysulfonyl, C 3 -C 8 -halocycloalkoxycarbonyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, C 1 -C 6 -cyanoalkoxycarbonyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkynylcarbonyloxy, C 2 -C 6 -haloalkynylcarbonyloxy, cyanocarbonyloxy, C 1 -C 6 -cyanoalkylcarbonyloxy, C 3 -C 8 -cycloalkylsulphonyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylsulphonyloxy, C 3 -C 8 -halocycloalkylsulphonyloxy, C 2 -C 6 -alkenylsulphonyloxy, C 2 -C 6 -alkynylsulphonyloxy, C 1 -C 6 -cyanoalkylsulphonyloxy, C 2 -C 6 -haloalkenylsulphonyloxy, C 2 -C 6 -haloalkynylsulphonyloxy, C 2 -C 6 -alkynylcycloalkyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -cyanoalkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 2 -C 6 -alkenyloxycarbonyloxy, C 2 -C 6 -alkynyloxycarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyloxy, sulfilimines, sulfoximines, SF 5 and Z 2 Q 2 ;
R 9 and R 10 ; and or R 9 and R A together with the atoms to which they are attached may form a 3- to 10-membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R 17 ;
wherein,
R 12 is selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 13 and R 14 are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 15 is selected from the group consisting of hydrogen, hydroxy, halogen, NR b R c , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -cycloalkyl, and
R 16 is selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -cycloalkyl;
or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof.
18 . The compound of claim 17 , wherein L 1 is a direct bond.
19 . The compound of claim 17 , wherein A is phenyl.
20 . The compound of claim 17 , wherein L 1 is a direct bond and A is phenyl.
21 . The compound of claim 17 , wherein L 2 is the fragment of formula L 2a .
22 . The compound of claim 17 , wherein L 2 is the fragment of formula L 2b .
23 . The compound of claim 17 , wherein L 1 is a direct bond and L 2 is the fragment of formula L 2a .
24 . The compound of claim 17 , wherein L 1 is a direct bond and L 2 is the fragment of formula L 2b .
25 . The compound of claim 17 , The compound of claim 17 , wherein A is phenyl and L 2 is the fragment of formula L 2a .
26 . The compound of claim 17 , The compound of claim 17 , wherein A is phenyl and L 2 is the fragment of formula L 2b .
27 . The compound of claim 17 , wherein L 1 is a direct bond, A is phenyl, and L 2 is the fragment of formula L 2 a.
28 . The compound of claim 17 , wherein L 1 is a direct bond, A is phenyl, and L 2 is the fragment of formula L 2b .
29 . A method for producing an intermediate, the method comprising:
reacting the compound of claim 14 with hydroxyl amine hydrochloride.
30 . A method for producing an intermediate, the method comprising:
reacting the compound of claim 15 with hydroxyl amine hydrochloride.
31 . A method for producing an intermediate, the method comprising:
reacting the compound of claim 16 with hydroxyl amine hydrochloride.
32 . Use of the compound of claim 14 for the synthesis of compound of formula (l)
wherein:
R 1 is C 1 -C 2 -haloalkyl;
L 1 is a direct bond, —CR 2 R 3 —, —C(═O)—, —O—, —S(═O) 0-2 —, —NR 4 — or —CR 2 R 3 C(═O)—, wherein, an expression “-” at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A;
A is an aromatic or non-aromatic 5- or 6-membered carbocyclic ring, wherein the ring members of the non-aromatic carbocyclic ring are selected from C, C(═O), C(═S), C(═CR 2a R 3a ) and C═NR 6 ; or
A is an aromatic or non-aromatic 5- or 6-membered heterocyclic ring; wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(═O) 0-2 , and S(═O) 0-1 (═NR 6 ) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(═O), C(═S), C(═CR 2a R 3a ) and C═NR 6 ; and
wherein, A is unsubstituted or is substituted with one or more identical or different R A groups,
wherein, R A is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, SF 5 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio and C 1 -C 6 -haloalkylsulfinyl;
wherein, R A may be optionally substituted with one or more identical or different R a selected from halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy;
or
two R A together with the atoms to which they are attached may form a 3- to 10-membered aromatic or non-aromatic carbocyclic ring or ring system, or aromatic or non-aromatic heterocyclic ring or ring system which may be optionally substituted with one or more identical or different R a ,
R 4 , R 6 , R 6a , R 6b , and R 6c are independently selected from the group of hydrogen, cyano, hydroxy, NR b R c , (C═O)—R d , S(O) 0-2 R e , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylamino and C 3 -C 8 -cycloalkyl;
R b and R c are independently selected from the group of hydrogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl or C 3 -C 8 -halocycloalkyl,
R d is selected from the group of hydrogen, hydroxy, halogen, NR b R c , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl; and
R e is selected from the group of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl;
L 2 is a fragment selected from the group of
wherein, k is an integer ranging from 0 to 4; an expression “#” indicates the point of attachment;
wherein, in Formula I when R 1 is CF 3 ; A is phenyl ring or C 3 -C 7 carbocyclic ring or 5- to 6-membered heterocyclic ring; L 2 is L 2 a wherein S atom of L 2 a is attached to A, and k=0 then R 10 is not hydrogen, cyano, nitro, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
wherein, in Formula I when R 1 is CF 3 ; A is phenyl ring or 5- to 6-membered heteroaromatic ring L 2 is L 2b , wherein S atom of L 2b is attached to A, and k=0 to 4 then R 10 is not cyano, nitro, R 11 and OR 11 ; wherein, R 11 is hydrogen, C 1 -C 6 -alkyl optionally substituted with a group selected from halogen, cyano, nitro, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, and phenyl ring optionally substituted with C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy;
R 2 , R 3 , R 2a , R 3a , R 2b , R 3b , R 2c , R 3c , R 2d , R 3d , R 2e , R 3e , R 7 and R 8 are independently selected from hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; or
R 2 and R 3 ; R 2a and R 3a ; R 2b and R 3b ; R 2c and R 3c ; R 2d and R 3d ; R 2e and R 3e ; and or R 7 and R 8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -alkoxy;
R 9 is selected from the group consisting of hydrogen; NR g R h , wherein, R g and R h independently represent hydrogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 3 -C 8 -cycloalkyl; (C═O)—R i , wherein, R i represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -haloalkoxy; C 1-8 -alkyl-S(O) 0-2 R j , wherein R j represents hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl; C 1 -C 6 -alkyl-(C═O)—R i , CR i ═NR g , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 4 -C 8 -cycloalkenyl, C 5 -C 8 -cycloalkynyl, C 7 -C 19 -aralkyl;
wherein, R 9 may optionally be substituted with one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl and di-C 1 -C 6 -alkylaminocarbonyl;
R 10 is selected from the group consisting of halogen, hydroxy, cyano, —OR 12 , —NR 13 R 14 , nitro, —SH, —SCN, —COR 15 , —C(═O)OR 12 , —C(═O)NR 13 R 14 , —NR 13 C(═O)R 15 , —O(C═O)R 15 , —O(C═O)NR 13 R 14 , —C(═NOR 13 )R 15 , —NR 13 SO 2 R 16 , —CSR 16 , —C(═S)OR 12 , —C(═S)NR 13 R 14 , —NR 13 C(═S)R 15 , —O(C═S)R 15 , —O(C═S)NR 13 R 14 , —O(C═S)SR 16 , —N═C(R 15 ) 2 , —NHCN, —SO 2 NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO 2 NR 12 R 13 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -thioalkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylamino-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkylamino, C 3 -C 8 -cycloalkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -hydroxyalkenyl, C 2 -C 6 -hydroxyalkynyl, C 3 -C 8 -halocycloalkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfinyl, tri-C 1 -C 6 -alkylsilyl, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, C 1 -C 6 -alkylcarbonylthio, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylsulfinyloxy, C 6 -C 10 -arylsulfonyloxy, C 6 -C 10 -arylsulfinyloxy, C 6 -C 10 -arylsulfonyl, C 6 -C 10 -arylsulfinyl, C 6 -C 10 -arylthio, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenylcarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylthio, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy, C 2 -C 6 -haloalkenylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkynyl, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -haloalkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxycarbonylamino, di(C 1 -C 6 -haloalkyl)amino-C 1 -C 6 -alkyl, C 3 -C 8 -halocycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -haloalkylsulfonylaminocarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, C 1 -C 6 -alkoxycarbonylalkoxy, C 1 -C 6 -alkylaminothiocarbonylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthiocarbonyl, C 3 -C 8 -cycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxycarbonyl, di-C 1 -C 6 -alkylaminothiocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkoxy, C 3 -C 8 -halocycloalkoxy-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 -alkylthiocarbonyloxy, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkylsulfonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkyl, di(C 1 -C 6 -haloalkyl)amino, di-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyloxy, tri-C 1 -C 6 -alkylsilyloxy, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyl, cyano(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxysulfonyl, C 3 -C 8 -halocycloalkoxycarbonyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, C 1 -C 6 -cyanoalkoxycarbonyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkynylcarbonyloxy, C 2 -C 6 -haloalkynylcarbonyloxy, cyanocarbonyloxy, C 1 -C 6 -cyanoalkylcarbonyloxy, C 3 -C 8 -cycloalkylsulphonyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylsulphonyloxy, C 3 -C 8 -halocycloalkylsulphonyloxy, C 2 -C 6 -alkenylsulphonyloxy, C 2 -C 6 -alkynylsulphonyloxy, C 1 -C 6 -cyanoalkylsulphonyloxy, C 2 -C 6 -haloalkenylsulphonyloxy, C 2 -C 6 -haloalkynylsulphonyloxy, C 2 -C 6 -alkynylcycloalkyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -cyanoalkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 2 -C 6 -alkenyloxycarbonyloxy, C 2 -C 6 -alkynyloxycarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyloxy, sulfilimines, sulfoximines, SF 5 and Z 1 Q 1 ;
Z 1 and Z 2 are independently a direct bond, CR 2d R 3d , N, O, C(O), C(S), C(═CR 2d R 3d ) or S(O) 0-2 ;
Q 1 and Q 2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R 17 ; or
Q 1 and Q 2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15-membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O) 0-2 , and C ring member of the non-aromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(═CR 2c R 3c ) or C(═NR 6b ), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R 17 ;
wherein, R 17 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, —OR 12 , —NR 13 R 14 , nitro, —SH, —SCN, —COR 15 , —C(═O)OR 12 , —C(═O)NR 13 R 14 , —NR 13 C(═O)R 15 , —O(C═O)R 15 , —O(C═O)NR 13 R 14 , —C(═NOR 13 )R 15 , —NR 13 SO 2 R 16 , —CSR 16 , —C(═S)OR 12 , —C(═S)NR 13 R 14 , —NR 13 C(═S)R 15 , —O(C═S)R 15 , —O(C═S)NR 13 R 14 , —O(C═S)SR 16 , —N═C(R 15 ) 2 , —NHCN, —SO 2 NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO 2 NR 12 R 13 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -thioalkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylamino-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkylamino, C 3 -C 8 -cycloalkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -hydroxyalkenyl, C 2 -C 6 -hydroxyalkynyl, C 3 -C 8 -halocycloalkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfinyl, tri-C 1 -C 6 -alkylsilyl, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, C 1 -C 6 -alkylcarbonylthio, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylsulfinyloxy, C 6 -C 10 -arylsulfonyloxy, C 6 -C 10 -arylsulfinyloxy, C 6 -C 10 -arylsulfonyl, C 6 -C 10 -arylsulfinyl, C 6 -C 10 -arylthio, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenylcarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylthio, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy, C 2 -C 6 -haloalkenylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkynyl, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -haloalkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxycarbonylamino, di(C 1 -C 6 -haloalkyl)amino-C 1 -C 6 -alkyl, C 3 -C 8 -halocycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -haloalkylsulfonylaminocarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, C 1 -C 6 -alkoxycarbonylalkoxy, C 1 -C 6 -alkylaminothiocarbonylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthiocarbonyl, C 3 -C 8 -cycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxycarbonyl, di-C 1 -C 6 -alkylaminothiocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkoxy, C 3 -C 8 -halocycloalkoxy-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 -alkylthiocarbonyloxy, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkylsulfonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkyl, di(C 1 -C 6 -haloalkyl)amino, di-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyloxy, tri-C 1 -C 6 -alkylsilyloxy, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyl, cyano(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxysulfonyl, C 3 -C 8 -halocycloalkoxycarbonyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, C 1 -C 6 -cyanoalkoxycarbonyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkynylcarbonyloxy, C 2 -C 6 -haloalkynylcarbonyloxy, cyanocarbonyloxy, C 1 -C 6 -cyanoalkylcarbonyloxy, C 3 -C 8 -cycloalkylsulphonyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylsulphonyloxy, C 3 -C 8 -halocycloalkylsulphonyloxy, C 2 -C 6 -alkenylsulphonyloxy, C 2 -C 6 -alkynylsulphonyloxy, C 1 -C 6 -cyanoalkylsulphonyloxy, C 2 -C 6 -haloalkenylsulphonyloxy, C 2 -C 6 -haloalkynylsulphonyloxy, C 2 -C 6 -alkynylcycloalkyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -cyanoalkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 2 -C 6 -alkenyloxycarbonyloxy, C 2 -C 6 -alkynyloxycarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyloxy, sulfilimines, sulfoximines, SF 5 and Z 2 Q 2 ;
R 9 and R 10 ; and or R 9 and R A together with the atoms to which they are attached may form a 3- to 10-membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R 17 ;
wherein,
R 12 is selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 13 and R 14 are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 15 is selected from the group consisting of hydrogen, hydroxy, halogen, NR b R c , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -cycloalkyl, and
R 16 is selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -cycloalkyl.
33 . Use of the compound of claim 17 for the synthesis of compound of formula (1)
wherein:
R 1 is C 1 -C 2 -haloalkyl;
L 1 is a direct bond, —CR 2 R 3 —, —C(═O)—, —O—, —S(═O) 0-2 —, —NR 4 — or —CR 2 R 3 C(═O)—, wherein, an expression “-” at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A;
A is an aromatic or non-aromatic 5- or 6-membered carbocyclic ring, wherein the ring members of the non-aromatic carbocyclic ring are selected from C, C(═O), C(═S), C(═CR 2a R 3a ) and C═NR 6 ; or
A is an aromatic or non-aromatic 5- or 6-membered heterocyclic ring; wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(═O) 0-2 , and S(═O) 0-1 (═NR 6 ) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(═O), C(═S), C(═CR 2a R 3a ) and C═NR 6 ; and
wherein, A is unsubstituted or is substituted with one or more identical or different R A groups,
wherein, R A is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, SF 5 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio and C 1 -C 6 -haloalkylsulfinyl;
wherein, R A may be optionally substituted with one or more identical or different R a selected from halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy;
or
two R A together with the atoms to which they are attached may form a 3- to 10-membered aromatic or non-aromatic carbocyclic ring or ring system, or aromatic or non-aromatic heterocyclic ring or ring system which may be optionally substituted with one or more identical or different R a ,
R 4 , R 6 , R 6a , R 6b , and R 6c are independently selected from the group of hydrogen, cyano, hydroxy, NR b R c , (C═O)—R d , S(O) 0-2 R e , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylamino and C 3 -C 8 -cycloalkyl;
R b and R c are independently selected from the group of hydrogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl or C 3 -C 8 -halocycloalkyl,
R d is selected from the group of hydrogen, hydroxy, halogen, NR b R c , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl; and
R e is selected from the group of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl;
L 2 is a fragment selected from the group of
wherein, k is an integer ranging from 0 to 4; an expression “#” indicates the point of attachment;
wherein, in Formula I when R 1 is CF 3 ; A is phenyl ring or C 3 -C 7 carbocyclic ring or 5- to 6-membered heterocyclic ring; L 2 is L 2a wherein S atom of L 2a is attached to A, and k=0 then R 10 is not hydrogen, cyano, nitro, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
wherein, in Formula I when R 1 is CF 3 ; A is phenyl ring or 5- to 6-membered heteroaromatic ring L 2 is L 2b , wherein S atom of L 2b is attached to A, and k=0 to 4 then R 10 is not cyano, nitro, R 11 and OR 11 ; wherein, R 11 is hydrogen, C 1 -C 6 -alkyl optionally substituted with a group selected from halogen, cyano, nitro, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, and phenyl ring optionally substituted with C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy;
R 2 , R 3 , R 2a , R 3 , R 2b , R 3b , R 2c , R 3c , R 2d , R 3d , R 2e , R 3e , R 7 and R 8 are independently selected from hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; or
R 2 and R 3 ; R 2a and R 3a ; R 2b and R 3b ; R 2c and R 3c ; R 2d and R 3d ; R 2e and R 3e ; and or R 7 and R 8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -alkoxy;
R 9 is selected from the group consisting of hydrogen; NR g R h , wherein, R g and R h independently represent hydrogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 3 -C 8 -cycloalkyl; (C═O)—R i , wherein, R i represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -haloalkoxy; C 1-8 -alkyl-S(O) 0-2 R j , wherein R j represents hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl; C 1 -C 6 -alkyl-(C═O)—R i , CR i ═NR g , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 4 -C 8 -cycloalkenyl, C 5 -C 8 -cycloalkynyl, C 7 -C 19 -aralkyl;
wherein, R 9 may optionally be substituted with one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl and di-C 1 -C 6 -alkylaminocarbonyl;
R 10 is selected from the group consisting of halogen, hydroxy, cyano, —OR 12 , —NR 13 R 14 , nitro, —SH, —SCN, —COR 15 , —C(═O)OR 12 , —C(═O)NR 13 R 14 , —NR 13 C(═O)R 15 , —O(C═O)R 15 , —O(C═O)NR 13 R 14 , —C(═NOR 13 )R 15 , —NR 13 SO 2 R 16 , —CSR 16 , —C(═S)OR 12 , —C(═S)NR 13 R 14 , —NR 13 C(═S)R 15 , —O(C═S)R 15 , —O(C═S)NR 13 R 14 , —O(C═S)SR 16 , —N═C(R 15 ) 2 , —NHCN, —SO 2 NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO 2 NR 12 R 13 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -thioalkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylamino-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkylamino, C 3 -C 8 -cycloalkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -hydroxyalkenyl, C 2 -C 6 -hydroxyalkynyl, C 3 -C 8 -halocycloalkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfinyl, tri-C 1 -C 6 -alkylsilyl, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, C 1 -C 6 -alkylcarbonylthio, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylsulfinyloxy, C 6 -C 10 -arylsulfonyloxy, C 6 -C 10 -arylsulfinyloxy, C 6 -C 10 -arylsulfonyl, C 6 -C 10 -arylsulfinyl, C 6 -C 10 -arylthio, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenylcarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylthio, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy, C 2 -C 6 -haloalkenylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkynyl, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -haloalkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxycarbonylamino, di(C 1 -C 6 -haloalkyl)amino-C 1 -C 6 -alkyl, C 3 -C 8 -halocycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -haloalkylsulfonylaminocarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, C 1 -C 6 -alkoxycarbonylalkoxy, C 1 -C 6 -alkylaminothiocarbonylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthiocarbonyl, C 3 -C 8 -cycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxycarbonyl, di-C 1 -C 6 -alkylaminothiocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkoxy, C 3 -C 8 -halocycloalkoxy-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 -alkylthiocarbonyloxy, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkylsulfonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkyl, di(C 1 -C 6 -haloalkyl)amino, di-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyloxy, tri-C 1 -C 6 -alkylsilyloxy, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyl, cyano(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxysulfonyl, C 3 -C 8 -halocycloalkoxycarbonyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, C 1 -C 6 -cyanoalkoxycarbonyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkynylcarbonyloxy, C 2 -C 6 -haloalkynylcarbonyloxy, cyanocarbonyloxy, C 1 -C 6 -cyanoalkylcarbonyloxy, C 3 -C 8 -cycloalkylsulphonyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylsulphonyloxy, C 3 -C 8 -halocycloalkylsulphonyloxy, C 2 -C 6 -alkenylsulphonyloxy, C 2 -C 6 -alkynylsulphonyloxy, C 1 -C 6 -cyanoalkylsulphonyloxy, C 2 -C 6 -haloalkenylsulphonyloxy, C 2 -C 6 -haloalkynylsulphonyloxy, C 2 -C 6 -alkynylcycloalkyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -cyanoalkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 2 -C 6 -alkenyloxycarbonyloxy, C 2 -C 6 -alkynyloxycarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyloxy, sulfilimines, sulfoximines, SF 5 and Z 1 Q 1 ;
Z 1 and Z 2 are independently a direct bond, CR 2d R 3d , N, O, C(O), C(S), C(═CR 2d R 3d ) or S(O) 0-2 ;
Q 1 and Q 2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R 17 ; or
Q 1 and Q 2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15-membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O) 0-2 , and C ring member of the non-aromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(═CR 2c R 3c ) or C(═NR 6b ), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R 17 ;
wherein, R 17 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, —OR 12 , —NR 13 R 14 , nitro, —SH, —SCN, —COR 15 , —C(═O)OR 12 , —C(═O)NR 13 R 14 , —NR 13 C(═O)R 15 , —O(C═O)R 15 , —O(C═O)NR 13 R 14 , —C(═NOR 13 )R 15 , —NR 13 SO 2 R 16 , —CSR 16 , —C(═S)OR 12 , —C(═S)NR 13 R 14 , —NR 13 C(═S)R 15 , —O(C═S)R 15 , —O(C═S)NR 13 R 14 , —O(C═S)SR 16 , —N═C(R 15 ) 2 , —NHCN, —SO 2 NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO 2 NR 12 R 13 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -thioalkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylamino-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkylamino, C 3 -C 8 -cycloalkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -hydroxyalkenyl, C 2 -C 6 -hydroxyalkynyl, C 3 -C 8 -halocycloalkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfinyl, tri-C 1 -C 6 -alkylsilyl, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -haloalkylsulfonylamino, C 1 -C 6 -alkylcarbonylthio, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylsulfinyloxy, C 6 -C 10 -arylsulfonyloxy, C 6 -C 10 -arylsulfinyloxy, C 6 -C 10 -arylsulfonyl, C 6 -C 10 -arylsulfinyl, C 6 -C 10 -arylthio, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenylcarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylthio, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy, C 2 -C 6 -haloalkenylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkynyl, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -haloalkylcarbonyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxycarbonylamino, di(C 1 -C 6 -haloalkyl)amino-C 1 -C 6 -alkyl, C 3 -C 8 -halocycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -haloalkylsulfonylaminocarbonyl, C 1 -C 6 -alkylsulfonylaminocarbonyl, C 1 -C 6 -alkoxycarbonylalkoxy, C 1 -C 6 -alkylaminothiocarbonylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthiocarbonyl, C 3 -C 8 -cycloalkenyloxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxycarbonyl, di-C 1 -C 6 -alkylaminothiocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkoxy, C 3 -C 8 -halocycloalkoxy-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 -alkylthiocarbonyloxy, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkylsulfonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -haloalkyl, di(C 1 -C 6 -haloalkyl)amino, di-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylaminocarbonylamino, C 1 -C 6 -haloalkoxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylaminocarbonyl-C 1 -C 6 -alkylamino, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyloxy, tri-C 1 -C 6 -alkylsilyloxy, tri-C 1 -C 6 -alkylsilyl-C 2 -C 6 -alkynyl, cyano(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxysulfonyl, C 3 -C 8 -halocycloalkoxycarbonyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 2 -C 6 -alkynyloxycarbonyl, C 1 -C 6 -cyanoalkoxycarbonyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkynylcarbonyloxy, C 2 -C 6 -haloalkynylcarbonyloxy, cyanocarbonyloxy, C 1 -C 6 -cyanoalkylcarbonyloxy, C 3 -C 6 -cycloalkylsulphonyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylsulphonyloxy, C 3 -C 8 -halocycloalkylsulphonyloxy, C 2 -C 6 -alkenylsulphonyloxy, C 2 -C 6 -alkynylsulphonyloxy, C 1 -C 6 -cyanoalkylsulphonyloxy, C 2 -C 6 -haloalkenylsulphonyloxy, C 2 -C 6 -haloalkynylsulphonyloxy, C 2 -C 6 -alkynylcycloalkyloxy, C 2 -C 6 -cyanoalkenyloxy, C 2 -C 6 -cyanoalkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 2 -C 6 -alkenyloxycarbonyloxy, C 2 -C 6 -alkynyloxycarbonyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyloxy, sulfilimines, sulfoximines, SF 5 and Z 2 Q 2 ;
R 9 and R 10 ; and or R 9 and R A together with the atoms to which they are attached may form a 3- to 10-membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R 17 ;
wherein,
R 12 is selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 13 and R 14 are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 15 is selected from the group consisting of hydrogen, hydroxy, halogen, NR b R c , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -cycloalkyl, and
R 16 is selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl and C 3 -C 8 -cycloalkyl.Join the waitlist — get patent alerts
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