US 12,221,436 B2
Anthranilamides, their use as insecticide and processes for preparing the same
Phaneendrasai Karri, Andhra Pradesh (IN); Jagadish Pabba, Rajasthan (IN); Avinash Bapu More, Maharashtra (IN); Venkatesh Kotha, Telangana (IN); Nilesh Kshirsagar, Maharashtra (IN); Geetanjly, Uttarakhand (IN); Anil Kumar Verma, Himachal Pradesh (IN); Hagalavadi M. Venkatesha, Bengaluru Karnataka (IN); and Alexander G. M. Klausener, Bengaluru Karnataka (DE)
Assigned to PI INDUSTRIES LTD., Udaipur Rajasthan (IN)
Appl. No. 15/733,436
Filed by PI INDUSTRIES LTD., Udaipur Rajasthan (IN)
PCT Filed Jan. 21, 2019, PCT No. PCT/IB2019/050470
§ 371(c)(1), (2) Date Jul. 30, 2020,
PCT Pub. No. WO2019/150220, PCT Pub. Date Aug. 8, 2019.
Claims priority of application No. 201811003535 (IN), filed on Jan. 30, 2018.
Prior Publication US 2021/0363134 A1, Nov. 25, 2021
Int. Cl. C07D 405/14 (2006.01); A01N 43/56 (2006.01); C07D 401/14 (2006.01); C07D 409/14 (2006.01)
CPC C07D 405/14 (2013.01) [A01N 43/56 (2013.01); C07D 401/14 (2013.01); C07D 409/14 (2013.01)] 18 Claims
 
1. A compound of formula I,

OG Complex Work Unit Chemistry
wherein,
R1 is NR10R11;
R10 is selected from the group consisting of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;
R11 is 5-, 6- or 7-membered heterocyclic ring attached to N of R1 through a C atom of respective ring, said heterocyclic ring containing at least two hetero atoms selected from N, O and S(O)0-2; and at least one C of the heterocyclic ring may be optionally replaced with C(═O), C(═S), C(═CR6aR7a) and C(═NR5); said heterocyclic ring may be optionally substituted with one or more different or identical R16a;
wherein R16a is selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C1-C6 hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkoxycarbonyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 dialkylamino, C3-C6 cycloalkylamino, C1-C6 alkyl-C3-C6-cycloalkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 dialkylaminocarbonyl, C1-C6 alkoxycarbonyloxy, C1-C6 alkylaminocarbonyloxy, C1-C6 dialkylaminocarbonyloxy and C1-C6 trialkylsilyl;
or
R11 is selected from the group consisting of hydrogen, C1-C8 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C5-C15 multicyclic ring or ring system, C3-C8 cycloalkylalkyl, C3-C10 heterocyclic ring, and NRcRd; wherein the heteroatoms of the heterocyclic ring are selected from N, O, and S(O)0-2, and C ring member of the heterocyclic ring may be optionally replaced with C(═O) and C(═S); each optionally substituted with one or more different or identical substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 trialkylsilyl, C3-C6 heterocyclic ring, wherein the heteroatoms of the heterocyclic ring are selected from N, O, and S(O)0-2, and C ring member of the heterocyclic ring may be optionally replaced with C(═O) and C(═S); phenyl, benzoyl, phenoxy and 5- or 6-membered heteroaromatic rings;
each phenyl, benzoyl, phenoxy and 5- or 6 membered heteroaromatic ring is optionally substituted with one or more different or identical substituents independently selected from the group consisting of C1-C6 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, cyano, nitro, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C8 cycloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C8 dialkylaminocarbonyl, C1-C6 trialkylsilyl, C1-C6 alkoxy, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C8 cycloalkylamino, C1-C6 alkoxycarbonyl and C1-C6 alkylcarbonyl; or
R10 and R11 together with N atom to which they are attached may form a 3 to 8-membered heterocyclic ring; wherein the heteroatoms of the heterocyclic ring are selected from N, O, and S(O)0-2, and C ring member of the heterocyclic ring may be optionally replaced with C(═O), C(═S) or C(═NR5a); said heterocyclyl ring may be optionally substituted with one or more substituent R16b;
wherein R16b is selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C1-C6 hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkoxycarbonyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 dialkylamino, C3-C6 cycloalkylamino, C1-C6 alkyl-C3-C6-cycloalkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 dialkylaminocarbonyl, C1-C6 alkoxycarbonyloxy, C1-C6 alkylaminocarbonyloxy, C1-C6 dialkylaminocarbonyloxy and C1-C6 trialkylsilyl;
or
R1 is

OG Complex Work Unit Chemistry
R12 and R13 are independently selected from the group consisting of hydrogen, C1-C10 alkyl, C3-C8 cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl and C1-C6 alkylcarbonyl, wherein said aliphatic and cycloaliphatic groups may be optionally substituted with one or more different or identical Re,
each Re is independently selected from the group consisting of halogen, cyano, nitro, hydroxy, —SH, —SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl and C3-C8 cycloalkyl, wherein one or more CH2 groups may be replaced by a C(═O) group, said aliphatic and cycloaliphatic groups may be optionally substituted with halogen, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, —ORa, —NRcRd, —S(O)aRa, —S(O)aNRcRd, —C(═O) Ra, —C(═O)NRcRd, —C(═O)ORb, —C(═S)Ra, —C(═S)NRcRd, —C(═S)ORb, —C(═S)SRb, —C(═NRc)Rb, —C(═NRc) NRcRd, phenyl, benzyl, phenoxy and 4- to 6-membered heterocyclic ring; each of phenyl, benzyl, phenoxy and 4- to 6-membered heterocyclic ring optionally substituted with halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; or
two vicinal radicals Re taken together form a group ═O, ═CH(C1-C6 alkyl), ═C(C1-C6 alkyl) C1-C4-alkyl, ═N(C1-C6-alkyl) or ═NO(C1-C6-alkyl); or
R12 and R13 are independently selected from the group consisting of phenyl, benzyl, phenoxy and 4- to 6-membered heterocyclic ring optionally substituted with halogen, cyano, nitro, hydroxy, —SH, —SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, and C3-C8 cycloalkyl, wherein one or more CH2 groups may be replaced by a C(═O) group, said aliphatic and cycloaliphatic groups may be optionally substituted with halogen, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, —ORa, —NRcRd, —S(O)aRa, —S(O) aNRcRd, —C(═O)Ra, —C(═O)NRcRd, —C(═O)ORb, —C(═S)Ra, —C(═S)NRcRd, —C(═S)ORb, —C(═S)SRb, —C(═NRc)Rb, or —C(═NRc) NRcRd; or
R12 and R13 together represent a C2-C7 alkylene, C2-C7 alkenylene, C6-C9 alkynylene, 3 to 10 membered ring or ring system together with the sulfur atom to which they are attached, wherein 1 to 4 of the CH2 groups in the C2-C7 alkylene chain or 1 to 4 of any of the CH2 or CH groups in the C2-C7 alkenylene chain or 1 to 4 of any of the CH2 groups in the C6-C9 alkynylene chain may be replaced by 1 to 4 groups independently selected from C(═O), C(═S), O, S, N, NO, SO, SO2 or NH, and wherein the carbon and/or nitrogen atoms in the C2-C7 alkylene, C2-C7 alkenylene or C6-C9 alkynylene ring may be optionally substituted with one or more different or identical substituents independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl and C2-C6 haloalkynyl;
Ra, Rb, Rc, Rd, R5 and R5a are selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyland C1-C6 alkylsulfonyl, wherein one or more CH2 groups may be replaced by a C(═O) group, and optionally substituted with halogen, C1-C6 alkoxy, phenyl, benzyl, pyridyl or phenoxy, wherein phenyl, benzyl, pyridyl and phenoxy may be optionally substituted with halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylamino and di-(C1-C6-alkyl)amino; or
Rc and Rd together with the nitrogen atom to which they are bound may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or unsaturated heterocyclic ring or ring system which may contain one or more ring members selected from N, O, S, SO and SO2, where the heterocyclic ring or ring system optionally may be substituted with halogen, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;
R14 is selected from the group consisting of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl and C1-C6 alkoxycarbonyl, each of which is optionally substituted with one or more different or identical group selected from the group consisting of halogen, C1-C6 alkoxy, C1-C6 alkylthio, cyano, nitro, formyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkyl, phenyl and naphthyl, wherein phenyl or naphthyl is optionally substituted with one or more different or identical group selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano; or
R14 is selected from the group consisting of C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C10 cycloalkenyl, phenyl, naphthyl, 3- to 8-membered ring or ring system which may contain at least one ring member selected from C, N, O, S, SO and SO2; each of which is optionally substituted with one or more different or identical group selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano;
B1 and B2 both are C,
W1 and W2 are independently O or S;
when B1 and B2 both are C then two R3 together with the carbon atoms to which they are attached may form a 5- to 11-membered carbocyclic, or aryl or heterocyclic or heteroaryl ring or ring system which may be optionally substituted with R2;
each of R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C1-C6 hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkoxycarbonyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 dialkylamino, C3-C6 cycloalkylamino, C1-C6 alkyl-C3-C6-cycloalkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 dialkylaminocarbonyl, C1-C6 alkoxycarbonyloxy, C1-C6 alkylaminocarbonyloxy, C1-C6 dialkylaminocarbonyloxy, C1-C6 trialkylsilyl, C1-C6 alkoxycarbonylamino, C1-C6 alkylaminocarbonylamino, C1-C6 dialkylaminocarbonylamino, C1-C6 haloalkylcarbonyl and a group RxON═C(Ry)—; wherein Rx and Ry are independently selected from the group consisting of hydrogen, C1-C6 alkyl, phenyl, benzyl, phenoxy and 4- to 6-membered heterocyclic ring;
each of phenyl, benzyl, phenoxy or 4- to 6-membered heterocyclic ring substituted with one or more different or identical substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C1-C6 hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 dialkylamino, C3-C6 cycloalkylamino, C1-C6 alkyl-C3-C6-cycloalkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 dialkylaminocarbonyl, C1-C6 alkoxycarbonyloxy, C1-C6 alkylaminocarbonyloxy, C1-C6 dialkylaminocarbonyloxy and C1-C6 trialkylsilyl;
each of R2 and R3 are independently selected from the group consisting of amino, formyl, C2-C6 cyanoalkenyl, C1-C6 alkylcarbonylamino, phenylcarbonylamino, phenyloxycarbonyl, 2—, 3- or 4 pyridylcarbonylamino; each of may be optionally substituted with one or more halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C1-C6 hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 dialkylamino, C3-C6 cycloalkylamino, C1-C6 alkyl-C3-C6 cycloalkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 dialkylaminocarbonyl, C1-C6 alkoxycarbonyloxy, C1-C6 alkylaminocarbonyloxy, C1-C6 dialkylaminocarbonyloxy and C1-C6 trialkylsilyl;
“m” is an integer ranging from 0 to 4;
R4 is selected from the group consisting of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl; wherein each of C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl is optionally substituted by one or more different or identical substituents selected from halogen nitro, cyano, hydroxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 dialkylamino, C3-C8 cycloalkyl, C3-C6 cycloalkylamino and C1-C6 alkyl-C3-C6 cycloalkylamino;
D is

OG Complex Work Unit Chemistry
wherein,
the expression

OG Complex Work Unit Chemistry
indicates the point of attachment to either Z1 or to the carbon marked with 2; and
R8 and R9 may be attached to one or more possible position/s,
R8 is selected from the group consisting of hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C1-C6 haloalkyl, halogen, cyano, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfinyl and C1-C6 haloalkylsulfonyl;
R9 is selected from the group consisting of a phenyl ring, a benzyl ring, a 5- or 6-membered heteroaromatic ring, a naphthyl ring system or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system optionally substituted with one or more different or identical substituents independently selected from halogen, C1-C6 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, cyano, nitro, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino, C1-C8 dialkylamino, C1-C6 cycloalkylamino, C3-C8 cycloalkyl-C1-C6-alklyamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C8 dialkylaminocarbonyl and C1-C6 trialkylsilyl;
Z1 is independently a direct bond or CR6R7 or C(═O) or C(═S) or O or S(O)0-2;
R6, R7, R6a, R7a, R6c, R7c, Rod and R7d are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxy, —CHO, C1-C6 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C6 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C1-C6 alkoxyalkyl, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinylalkyl, C1-C6 alkylsulfonylalkyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C5 alkoxycarbonyl-C1-C4-alkyl, C1-C5 alkylaminocarbonyl, C1-C5 dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
E is membered heterocyclic ring, wherein the heteroatoms are selected from N, O, and S(O)0-2, and C ring member of the heterocyclic may be replaced with C(═O), C(═S), C(═CR6cR7c), C(═NR5), or —S(═O)0-1 (═NR5)—; said membered heterocyclic ring is attached to Z1 through C or N; and
said heterocyclic ring is optionally substituted with one or more identical or different R15;
R15 is selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C3-C8 cycloalkoxy, C1-C6 hydroxyalkyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkylthio, C1-C6 alkylamino, C1-C6 dialkylamino, C3-C8 cycloalkylamino, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 halocycloalkyl, C1-C6 haloalkoxy, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkoxy-C1-C4-alkyl, C3-C8 cycloalkyl-C1-C6 alkyl, C3-C8 cycloalkyl-C1-C6-alkyl-amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxycarbonylamino, C1-C6 haloalkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 dialkylaminocarbonyl, C1-C6 alkoxycarbonyloxy, C1-C6 alkylaminocarbonyloxy C1-C6 dialkylaminocarbonyloxy and C1-C6 alkoxycarbonylamino; or
two geminal R15 together with the atom to which they are attached may form a substituted or unsubstituted spirocyclic ring or ring system, wherein the ring members of the spirocyclic ring or ring system are selected from C, N, O, and S(O)0-2, and C ring member of the spirocyclic ring or ring system may be replaced with C(═O), C(═S), C(═CR6dR7d), C(═NR5); or
two R15 together with the atoms to which they are attached may form a substituted or unsubstituted carbocyclic or heterocyclic ring or ring system, wherein the ring members of the carbocyclic ring or ring system are selected from C, C(═O), C(═S), C(═CR6dR7d), C(═NR5); and the ring members of the heterocyclic ring or ring system besides C include N, O, and S(O)0-2, and C ring member of the heterocyclic may be replaced with C(═O), C(═S), C(═CR6dR7d), C(═NR5);
wherein, the substituents on the spirocyclic ring or ring system formed by two geminal R15; or the carbocyclic ring or ring system the heterocyclic ring or ring system formed by two R15 are selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C3-C8 cycloalkoxy, C1-C6 hydroxyalkyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkylthio, C1-C6 alkylamino, C1-C6 dialkylamino, C3-C8 cycloalkylamino, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 halocycloalkyl, C1-C6 haloalkoxy, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkoxy-C1-C4-alkyl, C3-C8 cycloalkyl-C1-C6 alkyl, C3-C8 cycloalkyl-C1-C6-alkyl-amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxycarbonylamino, C1-C6 haloalkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 dialkylaminocarbonyl, C1-C6 alkoxycarbonyloxy, C1-C6 alkylaminocarbonyloxy, C1-C6 dialkylaminocarbonyloxy and C1-C6 alkoxycarbonylamino;
or salts, metal complexes, N-oxides, stereoisomers, or polymorphs thereof.