US 12,459,934 B2
Pesticidal compounds
Arun Narine, Ludwigshafen (DE); Rupsha Chaudhuri, Navi Mumbai (IN); Pulakesh Maity, Navi Mumbai (IN); Sunderraman Sambasivan, Mumbai (IN); Wolfgang von Deyn, Ludwigshafen (DE); Joachim Dickhaut, Ludwigshafen (DE); Nikolas Huwyler, Ludwigshafen (DE); Karsten Koerber, Ludwigshafen (DE); and Olesya Kuzmina, Ludwigshafen (DE)
Assigned to BASF SE, Ludwigshafen (DE)
Appl. No. 17/291,402
Filed by BASF SE, Ludwigshafen (DE)
PCT Filed Nov. 18, 2019, PCT No. PCT/EP2019/081580
§ 371(c)(1), (2) Date May 5, 2021,
PCT Pub. No. WO2020/109039, PCT Pub. Date Jun. 4, 2020.
Claims priority of application No. 18208775 (EP), filed on Nov. 28, 2018.
Prior Publication US 2022/0002284 A1, Jan. 6, 2022
Int. Cl. C07D 417/12 (2006.01); A01N 25/30 (2006.01); A01N 43/54 (2006.01); A01N 43/58 (2006.01); A01N 43/78 (2006.01); A01N 47/34 (2006.01); C07D 217/26 (2006.01); C07D 237/30 (2006.01); C07D 239/88 (2006.01); C07D 239/94 (2006.01); C07H 99/00 (2006.01)
CPC C07D 417/12 (2013.01) [A01N 25/30 (2013.01); A01N 43/54 (2013.01); A01N 43/58 (2013.01); A01N 43/78 (2013.01); A01N 47/34 (2013.01); C07D 217/26 (2013.01); C07D 237/30 (2013.01); C07D 239/88 (2013.01); C07D 239/94 (2013.01); C07H 99/00 (2013.01)] 12 Claims
 
1. A compound of formula I

OG Complex Work Unit Chemistry
wherein
A1 is N or CRA1;
A2 is N or CRA2;
A3 is N or CRA3;
wherein at least one of the A1, A2, A3 is N;
B1 is CRB1;
B2 is CRB2;
B3 is CRB3;
RA1, RA2, and RA3 independently of each other are selected from H, 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, C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio, or —CH2-phenyl,
wherein the phenyl rings are unsubstituted or substituted with Rf;
RB1, RB2, and RB3, independently of each other are H, 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, C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio, or —CH2-phenyl,
wherein the phenyl rings are unsubstituted or substituted with Rf;
Q is —N═C(X)—, —N(R2)—C(═NR)—, or —N(R2)—C(═S)—, —C(R4R5)—O—, —C(═O)—O—, —S(═O)m—C(R7R8)—, —N(R2)—S(═O) m—, —N(R2)—C(R9R10)—, —C(═O)—C(R19R20)—, —N(R2)—C(═O)—, —C(R13R14)—C(R15R16)—, or —C(R17)═C(R18)—; wherein Ar is bound to either side of Q;
X is identical or different, H, halogen, SR7, OR8, N(R3) 2, —CR4═N (OCH3), CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl moieties are unsubstituted or substituted with halogen;
phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
R is identical or different, H, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl moieties are unsubstituted or substituted with halogen,
SR7, OR8, N(R3)2, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C(O)—ORa, C1-C6-alkylen-NRbRc, C1-C6-alkylen-CN, C(O)—NRbRc, C(O)—Rd, SO2NRbRc, S(═O)mRe, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
R3 is H, C1-C6-alkyl, C1-C6-alkoxy, 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C1-C6-alkylene-CN, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
R4, R5, R7, R8, R9, R10, R13, R14, R15, R16, R17, R18, R19, R20 are, identical or different, H, halogen, 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C(═O)—ORa, C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, S(═O)mRe, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
R6 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C(═O)—ORa, C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, S(═O)mRe, phenyl, —CH2—C(═O)—ORa, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or substituted with RAr, wherein
RAr 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio or —CH2-phenyl, wherein phenyl rings are unsubstituted or substituted with Rf;
R1 is a moiety of formula Y—Z-T-R11 or Y—Z-T-R12; wherein
Y is —CRya═N—, wherein the N is bound to Z;
—NRyc—C(═O)—, wherein C(═O) is bound to Z; or
—NRyc—C(═S)—, wherein C(═S) is bound to Z;
Z is a single bond;
—NRzc—C(═O)—, wherein C(═O) is bound to T;
—NRzc—C(═S)—, wherein C(═S) is bound to T;
—N═C(S—Rza)—, wherein T is bound to the carbon atom;
—O—C(═O)—, wherein T is bound to the carbon atom; or
—NRzc—C(S—Rza)═, wherein T is bound to the carbon atom;
T is O, N or N-RT;
R11 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, C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, aryl, aryl-carbonyl, aryl-C1-C4-alkyl, aryloxy-C1-C4-alkyl, heteroaryl, carbonyl-heteroaryl, heteroaryl-C1-C4-alkyl or heteroaryloxy-C1-C4-alkyl, wherein the phenyl rings are unsubstituted or substituted with Rg and wherein the heteroaryl is a 5- or 6-membered monocyclic heteroaryl or a 8-, 9- or 10-membered bicyclic heteroaryl;
R12 is a radical of the formula A1;

OG Complex Work Unit Chemistry
wherein # indicates the point of attachment to T; or
R1 is

OG Complex Work Unit Chemistry
wherein

OG Complex Work Unit Chemistry
denotes attachment to the 10 membered hetaryl;
R121, R122, R123 are, identical or different, H, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkoxy-C1-C4-alkoxy, C1-C6-alkylcarbonlyoxy, C1-C6-alkenylcarbonlyoxy, C3-C6-cycloalkylcarbonlyoxy, wherein the alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and cycloalkyl moieties are unsubstituted or substituted with halogen, or NRbRc, or one of R121, R122, R123 may also be oxo;
R124 is H, C1-C6-alkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy, or C2-C6-alkenyloxy, wherein the alkyl, alkoxy, alkenyl and alkenyloxy moieties are unsubstituted or substituted with halogen;
and where
Rya is H, halogen, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C(═O)—ORa, C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, S(═O)mRe, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Ryc, Rzc are, identical or different, H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, or C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;
RT is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C(═O)—ORa, C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, S(═O)mRe, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Rzc together with RT if present, may form C1-C6-alkylene or a linear C2-C6-alkenylene group, where in the linear C1-C6-alkylene and the linear C2-C6-alkenylene a CH2 moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH2 moieties may be replaced by O or S and/or wherein the linear C1-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;
Rza is H, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, C1-C4-alkyl-C3-C6-cycloalkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, phenyl, phenylcarbonyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Rza together with RT if present, may form C1-C6-alkylene or a linear C2-C6-alkenylene group, where in the linear C1-C6-alkylene and the linear C2-C6-alkenylene a CH2 moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH2 moieties may be replaced by O or S and/or wherein the linear C1-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;
Ra, Rb and Rc are, identical or different, H, C1-C6-alkyl, C1-C6-alkoxy, 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C1-C6-alkylene-CN, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Rd 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Re is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen, phenyl and —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Rf 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-cycloalkoxyx-C1-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe;
Rg 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe;
Rh is halogen, OH, C1-C6-alkyl, C3-C6-cycloalkyl, or CN;
m is 0,1, or 2;
or an N-oxide, stereoisomer, tautomer, or agriculturally or veterinarily acceptable salt thereof.