Tricyclic pesticidal compounds

Patent metadata

Field	Value
Publication number	US-2023141433-A1
Application number	US-202117918135-A
Country	US
Kind code	A1
Filing date	Mar 31, 2021
Priority date	Apr 14, 2020
Publication date	May 11, 2023
Grant date	—

Abstract

The invention relates to compounds of formula (I), wherein the variables are as defined in the specification. It also relates to the use of compounds of formula (I) as an agrochemical pesticide; to pesticidal mixtures comprising compounds of formula (I); and to agrochemical or veterinary compositions comprising compounds of formula (I). Other objects are seed comprising compounds of formula (I); and methods for controlling invertebrate pests, infestation, or infection by invertebrate pests by application of compounds of formula (I).

First claim

1 . A compound of formula (I), or an agrochemically or veterinarily acceptable salt, stereoisomer, tautomer, or N-oxide thereof

wherein the variables in formula (I) have the following meaning,
A is CH, N, or NH;
E is N, O, S, NR E , or CR E ;
G, J are independently C or N;
L is N or CR L ;
M is N or CR M ;
Q is N or CR Q ;
T is N or CR T ;
V is N or CR V ;
W is N or CR W ;
R E , R L , R M , R Q , R T , R V , and R W are independently selected from H, halogen, N 3 , CN, NO 2 , SCN, SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, tri-C 1 -C 6 -alkylsilyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxyx-C 1 -C 4 -alkyl, which groups are unsubstituted or substituted with halogen;
C(═O)OR 1 , NR 2 R 3 , C 1 -C 6 -alkylen-NR 2 R 3 , O—C 1 -C 6 -alkylen-NR 2 R 3 , C 1 -C 6 -alkylen-CN, NH—C 1 -C 6 -alkylen-NR 2 R 3 , C(═O)NR 2 R 3 , C(═O)R 4 , SO 2 NR 2 R 3 , S(═O) q R 5 , OR 6 , SR 6 , phenyl, and benzyl, wherein the phenyl ring g is unsubstituted or substituted with one or more, same or different substituents R 11 ;
R 1 is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, or C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which groups are unsubstituted or substituted with halogen;
C 1 -C 6 -alkylen-NR 2 R 3 , C 1 -C 6 -alkylen-CN, or
phenyl or benzyl, wherein the phenyl ring is unsubstituted, or substituted with one or more, same or different substituents R 11 ;
R 11 is selected from halogen, N 3 , OH, CN, NO 2 , SCN, SF 5 ,
C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which groups are unsubstituted or substituted with halogen;

R 2 is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which groups are unsubstituted, or substituted with one or more, same or different substituent selected from halogen, CN and HO;
C(═O)R 21 , C(═O)OR 21 , C(═O)NR 21 , C 1 -C 6 -alkylen-CN, or phenyl or benzyl, wherein the phenyl ring is unsubstituted or substituted with one or more, same or different substituents R 11 ;
R 21 is H, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 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 R 11 ;

R 3 is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which groups are unsubstituted or substituted with halogen;
C 1 -C 6 -alkylen-CN, or phenyl or benzyl, wherein the phenyl ring is unsubstituted or substituted with one or more, same or different substituents R 1 ; or

NR 2 R 3 may also 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 0, S(═O) q , NH, and N—C 1 -C 6 -alkyl, and wherein the N-bound heterocycle is unsubstituted or substituted with one or more, same or different substituents selected from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy;
R 4 is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, or C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which groups are unsubstituted or substituted with one or more, same of different substituents selected from halogen, CN, and OH;
phenyl or benzyl, wherein the phenyl ring unsubstituted, or substituted with one or more, same or different substituents R 11 ;

R 5 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, or C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which groups are unsubstituted or substituted with halogen;
C 1 -C 6 -alkylen-NR 2 R 3 , C 1 -C 6 -alkylen-CN, phenyl or benzyl, wherein the phenyl ring is unsubstituted, or substituted with one or more, same or different substituents R 11 ;

R 6 is phenyl, which is unsubstituted or substituted with one or more, same or different substituents R 11 ;

D is a moiety of formula

wherein the “&”-symbol signifies the connection to the remainder of formula (I), wherein the dotted circle in the 5-membered ring means that the 5-membered ring may be saturated, partially unsaturated, or fully unsaturated;
R X is C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, which are unsubstituted or substituted with halogen; or
phenyl or benzyl, wherein the phenyl ring is unsubstituted or substituted with one or more, same or different substituents R 11 ;

X is N, S, O, CR 7 , or NR 8 ;
Y and Z are independently C or N, wherein at least one of the variables selected from Y and Z is C;
D* is a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated carbo- or heterocycle, which carbo- or heterocycle includes the atoms Y and Z as ring members and is unsubstituted or substituted with one or more, same or different substituents R 9 , and wherein said heterocycle comprises 0, 1, 2, or 3, same or different heteroatoms O, N, or S in addition to those that may be present as ring members Y and Z;
R 7 is H, halogen, OH, CN, NC, NO 2 , N 3 , SCN, NCS, NCO, SF 5 ,
C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkenyl, C 2 -C 6 -alkynyl, which groups are unsubstituted, or substituted with one or more, same or different substituents R G1 ;
a 3- to 12-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system 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 R H1 , and wherein said N- and S-atoms are independently oxidized, or non-oxidized;
phenyl, which is unsubstituted, or substituted with one or more, same or different substituents R J1 ;
OR K1 , SR K1 , OC(═O)R K1 , OC(═O)OR K1 , OC(═O)NR L1 R M1 , OC(═O)SR K1 , OC(═S)NR L1 R M1 , OC(═S)SR K1 , OS(═O) q R K1 , OS(═O) q NR L1 R M1 , ONR L1 R M1 , ON═CR N1 R O1 , NR L1 R M1 , NOR K1 , ONR L1 R M1 , N═CR N1 R O1 , NNR L1 , N(R L1 )C(═O)R K1 , N(R L1 )C(═O)OR K1 , S(═O) q R V1 , SC(═O)SR K1 , SC(═O)NR L1 R M1 , S(═O) q NR L1 R M1 , C(═O)R P1 , C(═S)R P1 , C(═O)NR L1 R M1 , C(═O)OR K1 , C(═S)NR L1 R M1 , C(═S)OR K1 , C(═S)SR K1 , C(═NR L1 )R M1 , C(═NR L1 )NR M1 R R1 , Si(R S1 ) 2 R T1 ;

R 8 is H, CN, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkenyl, C 2 -C 6 -alkynyl, which groups are unsubstituted or substituted with one or more, same or different substituents R G1 ;
a 3- to 12-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises

Assignees

• Basf Se

Inventors

• Shaikh Rizwan Shabbir
• Von Deyn Wolfgang
• Maity Pulakesh
• Schroeder Birte
• Chaudhuri Rupsha
• Sambasivan Sunderraman
• Adisechan Ashokkumar

Classifications

• A01P7/04

  Insecticides · CPC title

• A61K31/4375

  the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine · CPC title

• C07D519/00 Primary

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• C07D471/14

  Ortho-condensed systems · CPC title

• A61K31/437

  the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline · CPC title