US 12,134,616 B2
Tricyclic pesticidal compounds
Wolfgang Von Deyn, Ludwigshafen (DE); Rizwan Shabbir Shaikh, Navi Mumbai (IN); Devendra Vyas, Research Triangle Park, NC (US); Arun Narine, Ludwigshafen (DE); and Olesya Kuzmina, Ludwigshafen (DE)
Assigned to BASF SE, Ludwigshafen (DE)
Appl. No. 17/282,018
Filed by BASF SE, Ludwigshafen (DE)
PCT Filed Oct. 11, 2019, PCT No. PCT/EP2019/077562
§ 371(c)(1), (2) Date Apr. 1, 2021,
PCT Pub. No. WO2020/083662, PCT Pub. Date Apr. 30, 2020.
Claims priority of application No. 18202072 (EP), filed on Oct. 23, 2018.
Prior Publication US 2021/0347777 A1, Nov. 11, 2021
Int. Cl. C07D 471/14 (2006.01); A01N 43/90 (2006.01); C07D 471/04 (2006.01)
CPC C07D 471/14 (2013.01) [A01N 43/90 (2013.01); C07D 471/04 (2013.01)] 16 Claims
 
1. A compound of formula (I), or an agrochemically or veterinarily acceptable salt, stereoisomer, tautomer, or N-oxide thereof

OG Complex Work Unit Chemistry
wherein variables in formula (I) have the following meaning
A is CH, N, or NH;
E is N, O, S, NRE, or CRE;
G, J are independently C or N;
L is N or CRL;
M is N or CRM;
Q is N or CRQ;
T is N or CRT;
V is N or CRV;
W is N or CRW;
X is phenyl, or a 5- or 6-membered hetaryl;
Y is S, S(O), or S(O)2;
RE, RL, RM, RQ, RT, RV, and RW are independently H, halogen, N3, CN, NO2, SCN, SF5;
C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which groups are halogenated or non-halogenated;
C(═O)OR1, NR2R3, C1-C6-alkylen-NR2R3, O-C1-C6-alkylen-NR2R3, C1-C6-alkylen-CN, NH—C1-C6-alkylen-NR2R3, C(═O)NR2R3, C(═O)R4, SO2NR2R3, S(═O)mR5, OR6, SR6, or CH2R6;
phenyl, which is unsubstituted or substituted with one or more, same or different substituents R11;
R1 is H;
C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, which groups are halogenated or non-halogenated;
C1-C6-alkylen-NR2R3, C1-C6-alkylen-CN, or CH2R6; or
phenyl, which is unsubstituted, or substituted with one or more, same or different substituents R11;
R11 is halogen, N3, OH, CN, NO2, SCN, SF5;
C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which groups are halogenated or non-halogenated;
R2 is H;
C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which groups are unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN and OH;
C(═O)R21, C(═O)OR21, C(═O)NR21, C1-C6-alkylen-CN, or CH2R6; or
phenyl, which is unsubstituted or substituted with one or more, same or different substituents R11;
R21 is H;
 C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl;
 C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4 alkyl, phenyl, or a saturated, partially-, or fully unsaturated 5- or 6-membered heterocycle, wherein the cyclic moieties are unsubstituted or substituted with one or more, same or different substituents R11;
R3 is H;
C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which groups are halogenated or non-halogenated;
C1-C6-alkylen-CN, or CH2R6;
phenyl, which is unsubstituted or substituted with one or more, same or different substituents R11; or
NR2R3 form an N-bound, saturated 3- to 8-membered heterocycle, which in addition to the nitrogen atom may have 1 or 2 further heteroatoms or heteroatom moieties selected from O, S(═O)m, NH, and N—C1-C6-alkyl, and wherein the N-bound heterocycle is unsubstituted or substituted with one or more, same or different substituents selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
R4 is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, which are unsubstituted or substituted with one or more, same of different substituents selected from halogen, CN, and OH;
CH2R6, or phenyl, which is unsubstituted, or substituted with one or more, same or different substituents R11;
R5 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, which groups are halogenated or non-halogenated;
C1-C6-alkylen-NR2R3, C1-C6-alkylen-CN, CH2R6; or
phenyl, which is unsubstituted, or substituted with one or more, same or different substituents R11;
R6 is phenyl, which is unsubstituted or substituted with one or more, same or different substituents R11;
RX is halogen, N3, OH, CN, NO2, SCN, SF5;
C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which groups are halogenated or non-halogenated;
C(═O)OR1, NR2R3, C1-C6-alkylen-NR2R3, O-C1-C6-alkylen-NR2R3, C1-C6-alkylen-CN, NH—C1-C6-alkylen-NR2R3, C(═O)NR2R3, C(═O)R4, SO2NR2R3, S(═O)mR1, OR6, SR6, CH2R6; or OC(═O)R4, OC(═O)OR1, OC(═O)NR2R3, OC(═O)SR1, OC(═S)NR2R3, OC(═S)SR1, ONR2R3, ON═CR1R4, N═CR1R4, NNR2, NC(═O)R4, SC(═O)SR1, SC(═O)NR2R3, C(═S)R6, C(═S)OR4, C(═NR2)R4, C(═NOR2)R4, C(CN)R7R8;
phenyl, which is unsubstituted or substituted with one or more, same or different substituents R11;
a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents R31, and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or
C3-C6-cycloalkyl, which substituted with one or more, same or different substituents R9;
R7, R8 are independently H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylsulfanyl, C1-C4-alkylsulfanyl-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl or C1-C4-alkoxycarbonyl;
R9 CN, NH2, C(═O)H, OH, C3-C6-cycloalkyl, C(═O)OH, C(═O)NH2, C1-C4-haloalkoxy, C1-C4-alkoxy, C1-C4-haloalkylsulfanyl, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, di-(C1-C4)alkylaminocarbonyl, C1-C4-alkylaminocarbonyl, C1-C4-alkylcarbonylamino, di-(C1-C4)alkylcarbonylamino, C1-C4-alkoxycarbonylamino, or a group —C(R91)═NOR92;
phenyl, which is unsubstituted or substituted with one or more, same or different substituents selected from halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkoxy, C1-C4-haloalkylsulfanyl, C1-C4-haloalkylsulfinyl, C1-C4haloalkylsulfonyl and C(═O)C1-C4-haloalkyl;
C1-C4-alkyl which is unsubstituted or substituted with one or more, same or different substituents R93;
R31 is halogen, N3, OH, CN, NO2, SCN, SF5;
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl;
C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4 alkyl, phenyl, or a saturated, partially-, or fully unsaturated 5- or 6-membered heterocycle, wherein the cyclic moieties are unsubstituted or substituted with one or more, same or different substituents R11; or
two geminal substituents R31 form together with the atom to which they are bound a group ═O or ═S;
R91 and R92 are independently H, C1-C4-alkyl, or C1-C4-haloalkyl;
R93 is halogen, CN, NH2, C(═O)H, OH, C3-C6-cycloalkyl, hydroxycarbonyl, aminocarbonyl, C1-C4-haloalkoxy, C1-C4-alkoxy, C1-C4-haloalkylsulfanyl, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, di-(C1-C4)alkylaminocarbonyl, C1-C4alkylaminocarbonyl, C1-C4-alkylcarbonylamino, di-(C1-C4)alkylcarbonylamino, C1-C4-alkoxycarbonylamino, a group —C(R91)═NOR92;
RY is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which groups are halogenated or non-halogenated;
CH2R6, or phenyl, which is unsubstituted or substituted with R11;
the index n is 0, 1, 2, 3, or 4 if X is phenyl or a 6-membered hetaryl;
or 0, 1, 2, or 3 if X is a 5-membered hetaryl; and
the index m is 0, 1, or 2.