Substituted pyrimidinium compounds for combating animal pests

Patent metadata

Field	Value
Publication number	US-10149477-B2
Application number	US-201515517189-A
Country	US
Kind code	B2
Filing date	Oct 6, 2015
Priority date	Oct 6, 2014
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

Abstract

Substituted pyrimidinium compounds of the general formula (I):

wherein the compounds are useful for controlling invertebrate pests.

First claim

The invention claimed is:

1. A substituted pyrimidinium compound of formula (Iaa):

wherein
X and Y are each independently O or S;
Z is a direct bond, O, S(O) m , NR b , C(R aa R aa )O, C(═X 1 ), C(═X 1 )Y 1 or Y 1 C(═X 1 );
X 1 is O, S or NR b ;
Y 1 is O, S or NR c ;
A is CH;
B is CR′R″;
M 1 is S(O) m ;
R′ and R″ are each independently H, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, CN, OR c , NR b R c , NO 2 , C(═O)(O) p R c , OC(═O)(O) p R c , C(═O)NR b R c , OC(═O)NR b R c , NR b C(═O)(O) p R e , NR b C(═O)NR b R c , C(═S)NR b R c , S(O) m R b , SO 2 NR b R c , OSO 2 R c , OSO 2 NR b R c , NR b SO 2 R c , NR b SO 2 NR b R c , N═S(═O) p R c R c , S(═O) o (═NR b ) q R c , SF 5 , OCN, SCN, Si(R d ) 3 or a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N—(R c ) p , O, and S which may be oxidized, and wherein the aforementioned groups and the carbo- or heterocyclic ring may be partially or fully substituted by R′″,
R′″ is each independently halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy;
or
R′ and R″ together form a group selected from ═O, ═S, ═CR b R c , =NR c , =NOR c and =NNR c R c ;
Het is a three- to ten-membered heterocyclic ring or a seven- to eleven-membered heterocyclic ring system, each ring or ring system member selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N(R c ) p , wherein up to 3 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring members are independently selected from S(═O) o (═NR b ) q , each ring or ring system optionally substituted with up to 5 R a ;
o and q are each independently 0, 1 or 2, provided that the sum (o+q) is 0, 1 or 2 for each ring;
R 1 is hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 10 -cycloalkyl, C 4 -C 10 -cycloalkenyl, C 5 -C 14 -cycloalkylcycloalkyl or R 1 may form a three- to eleven-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring or ring system, which may contain 1 to 4 heteroatoms selected from N(R c ) p , O, and S, wherein S may be oxidized, and wherein the aforementioned groups and the carbo- or heterocyclic ring system may be unsubstituted, partially or fully substituted by R a ; or
R 1 is C(═O)R b , C(═O)OR e , NR b R c , C(═O)NR b R c , C(═S)NR b R c , SO 2 NR b R c , OC(═O)R c , OC(═O)OR e , OC(═O)NR b R c , N(R c )C(═O)R c , N(R c )C(═O)OR e , N(R c )C(═O)NR b R c , NR c SO 2 R b , NR c SO 2 NR b R c , Si(R d ) 3 , C(═NR c )R c , C(═NOR c )R c ′, C(═NNR b R c )R c , C(═NN(C(═O)R b )R c )R c , C(═NN(C=O)OR c )(R c ) 2 , S(═O) o (═NR b ) q R c or N=CR b R c ;
R a is each independently halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, CN, OR C , NR b R c , NO 2 , C(═O)(O) p R c , OC(═O)(O) p R e , C(═O)NR b R c , OC(═O)NR b R c , NR b C(═O)(O) p R e , NR b C(═O)NR b R c , C(═S)NR b R c , S(O) m R b , SO 2 NR b R c , OSO 2 R c , OSO 2 NR b R c , NR b SO 2 R c , NR b SO 2 NR b R c , N═S(═O) p R c R c , S(═O) o (═NR b ) q R c , SF 5 , OCN, SCN, Si(R d ) 3 or a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N—(R c ) p , O, and S which may be oxidized, and wherein the aforementioned groups and the carbo- or heterocyclic ring may be partially or fully substituted by R aa , or two geminally bound groups R a together may form a group selected from ═O, ═S, ═CR b R c , =NR c , =NOR c , and =NNR c R c ;
R aa is each independently hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy;
R b is each independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy or a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N(R c ) p , O, and S, wherein S may be oxidized and which carbo- or heterocyclic ring may be partially or fully substituted by R aa ;
R c is each independently hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 6 cycloalkyl, or a three- to six-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N(R aa ) p , O and S, wherein S may be oxidized and wherein the carbo- or heterocyclic ring may be partially or fully substituted by R aa ;
wherein two geminally bound groups R b R b , R c R b or R c R c together with the atom to which they are bound, may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 or 2 heteroatoms or heteroatoms groups selected from N, O, S, NO, SO and SO 2 and wherein the carbo- or heterocyclic ring may be partially or fully substituted by R bb ;
R bb is each independently halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, CN, OR c , NR b R c , NO 2 , C(═O)(O) p R c , OC(═O)(O) p R e , C(═O)NR b R c , OC(═O)NR b R c , NR b C(═O)(O) p R e , NR b C(═O)NR b R c , C(═S)NR b R c , S(O) m R b , SO 2 NR b R c , OSO 2 R c , OSO 2 NR b R c , NR b SO 2 R c , NR b SO 2 NR b R c , SF 5 , OCN, SCN, Si(R d ) 3 , C(═N(O) p R b )R b , C(═NNR b R c )R b , C(═NN(C(═O)O p R c )R b )R b , ON═CR b R c , ONR b R c , S(═O) o (═NR b ) q R c , SO 2 NR b (═O)NR b R c , P(═X 2 )R b R c , OP(═X 2 )(O p R c )R b , OP(═X 2 )(OR c ) 2 , N=CR b R c , RN b N=CR b R c , NR b NR b R c , NR b C(═S)NR b R c , NR b C(—NR b )NR b R c , NR b NR b C(═X 2 )NR b R c , NR b NR b SO 2 NR c , or N═S(═O) p R c R c or two geminally bound groups R bb together may form a group selected from ═O, ═S, ═CR b R c , =NR c , =NOR c , and =NNR c R c ;
R d is each independently hydrogen, phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, or C 1 -C 6 -alkoxyalkyl, wherein the above mentioned groups may be substituted by one or more halogen;
R e is each independently, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 6 cycloalkyl, or a three- to six-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N(R aa ) p , O and S, wherein S may be oxidized and wherein the carbo- or heterocyclic ring may be partially or fully substituted by R aa ;
m is 0, 1, or 2;
p is 0 or 1;
R 2 is H, halogen, CN, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 10 cycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, or C 3 -C 6 cycloalkenyl, wherein the aforementioned groups may be unsubstituted, partially, or fully substituted with R 2a , or R 2 may form a carbo- or heterocyclic three- to ten-membered ring or a seven- to eleven-membered ring system, which ring or ring system may be saturated, partially unsaturated, or aromatic, and which ring or ring system may contain 1 to 4 heteroatoms selected from N(R c ) p , O and S, wherein S may be oxidized, and wherein the carbo- or heterocyclic ring or ring system may be unsubstituted, partially or fully substituted by R 2a ;
with th

Assignees

• Basf Se

Inventors

• Dickhaut Joachim
• Narine Arun
• Von Deyn Wolfgang
• Koller Raffael
• Wach Jean-Yves
• Vyas Devendra
• Adisechan Ashokkumar
• Shinde Harish

Classifications

• C07D513/04 Primary

  Ortho-condensed systems · CPC title

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• A61K31/513

  having oxo groups directly attached to the heterocyclic ring, e.g. cytosine · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title