Pesticide Compounds

Patent metadata

Field	Value
Publication number	US-2016157491-A1
Application number	US-201414903887-A
Country	US
Kind code	A1
Filing date	Jul 14, 2014
Priority date	Jul 15, 2013
Publication date	Jun 9, 2016
Grant date	—

Abstract

The present invention relates to novel compounds of the formula I and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof

wherein C 1 is C or CH; C 2 is C or CH; A 1 is N or C; A 2 is N, C(R 2 ), N(R 3 ), O, S or C(R 4 ,R 5 ); and A 3 is N, O, S, N(R 6 ), C(R 7 ) or C(R 8 ,R 9 ); where one or two non-adjacent bonds in the 5-membered ring formed by C 1 , C 2 , A 1 , A 2 and A 3 are double bonds, while the others are single bonds, provided that the bond between A 1 and A 2 or the bond between A 1 and C 1 or the bond between A 2 and A 3 or the bond between C 1 and C 2 or the bond between A 3 and C 2 is a double bond further provided that at least one of A 1 , A 2 and A 3 is N, N(R 3 ) or N(R 6 ), and where Ar, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and (R) k are as defined in the claims and in the description,

which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

First claim

1 - 30 . (canceled)

31 : A compound of the formula (I)

wherein
C 1 is C or CH
C 2 is C or CH
A 1 is N or C
A 2 is N, C(R 2 ), N(R 3 ), O, S or C(R 4 ,R 5 ); and
A 3 is N, O, S, N(R 6 ), C(R 7 ) or C(R 8 ,R 9 );
where one or two non-adjacent bonds in the 5-membered ring formed by C 1 , C 2 , A 1 , A 2 and A 3 are double bonds, while the others are single bonds, provided that the bond between A 1 and A 2 or the bond between A 1 and C 1 or the bond between A 2 and A 3 or the bond between C 1 and C 2 or the bond between A 3 and C 2 is a double bond further provided that at least one of A 1 , A 2 and A 3 is N, N(R 3 ) or N(R 6 ),
and where
R 2 , R 7 independently of each other, are selected from the group consisting of hydrogen, halogen, N 3 , OH, CN, NO 2 , —SCN, —SF 5 ,
C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, 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 -cycloalkoxy-C 1 -C 4 -alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated,
C(O)—OR a , NR b R c , C 1 -C 6 -alkylen-NR b R c , O—C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, NH—C 1 -C 6 -alkylen-NR b R c ,
C(O)—NR b R c , C(O)—R d , SO 2 NR b R c and S(═O) m R e ;

R 3 , R 6 independently of each other, are selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, 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, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated,
C(O)—OR a , NR b R c , C 1 -C 6 -alkylen-NR b R c , O—C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, NH—C 1 -C 6 -alkylen-NR b R c ,
C(O)—NR b R c , C(O)—R d , SO 2 NR b R c , S(═O) m R e , phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R f ;

R 4 , R 5 independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio and C 1 -C 4 -haloalkylthio or C(R 4 ,R 5 ) may be a carbonyl group or thiocarbonyl group;
R 8 , R 9 independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio and C 1 -C 4 -haloalkylthio or C(R 8 ,R 9 ) may be a carbonyl group or thiocarbonyl group;

Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or carry 1, 2, 3 or 4 radicals R Ar , which are identical or different, where
R Ar independently of each other, are selected from the group consisting of halogen, N 3 , OH, CN, NO 2 , —SCN, —SF 5 ,
C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, 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 -cycloalkoxy-C 1 -C 4 -alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated,
C(O)—OR a , NR b R c , C 1 -C 6 -alkylen-NR b R c , O—C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, NH—C 1 -C 6 -alkylen-NR b R c ,
C(O)—NR b R c , C(O)—R d , SO 2 NR b R c and S(═O) m R e , one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio or benzyl, where the phenyl ring in the last 5 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R f ;

Q is —O—, —S—, —S(═O)—, —S(═O) 2 —, —C(R Q2a R Q2b )—, —N(R Q1 )—, —N(R Q2 )—C(═O)—, —O—C(═O)—, —C(R Q3 )═C(R Q4 )—, —C(R Q3a R Q3b )—C(R Q4a R Q4b )—, —C(R Q3a R Q3b )—C(═O)—, —O—C(R Q4a R Q4b )—, —S(═O) n —C(R Q4a R Q4b )— or —N(R Q2 )—C(R Q4a R Q4b )—, where
n is 0, 1 or 2;
R Q1 , R Q2 independently of each other are selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, 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, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated,
C(O)—OR a , NR b R c , C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, C(O)—NR b R c , C(O)—R d , SO 2 NR b R c , S(═O) m R e , phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R f ;

R Q3 , R Q4 independently of each other, are selected from the group consisting of hydrogen, halogen, OH, CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C(O)—OR a , NR b R c , C 1 -C 6 -alkylen-NR b R c , O—C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, NH—C 1 -C 6 -alkylen-NR b R c , C(O)—NR b R c , C(O)—R d , SO 2 NR b R c and S(═O) m R e ;
R Q2a , R Q2b independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio and C 1 -C 4 -haloalkylthio or —C(R Q2a R Q2b )— is C═O or C═S;
R Q3a , R Q3b independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio and C 1 -C 4 -haloalkylthio;
R Q4a , R Q4b independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio and C 1 -C 4 -haloalkylthio;

R 1 is a moiety of the formula —X—Y—Z—R 11 , where
R 11 is selected from the group consisting of 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, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, C(O)—NR b R c , C(O)—R d , aryl, arylcarbonyl, aryl-C 1 -C 4 -alkyl, aryloxy-C 1 -C 4 -alkyl, hetaryl, hetarylcarbonyl, hetaryl-C 1 -C 4 -alkyl and hetaryloxy-C 1 -C 4 -alkyl, where the aryl and hetaryl rings in the last 8 radicals are unsubstituted or carry 1, 2, 3, 4 or 5 radicals R g and where hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl;
X is a single bond, NR x1 , or a bivalent group —N(R x2 )—C(═O)—, where C═(O) is bound to Y, —N(R x2 )—C(═S)—, where C═(S) is bound to Y, or a bivalent group —C(R x3 )═N—, where the nitrogen is bound to Y,
Y is a bivalent group —N(R y1 )—C(═O)—, —N(R y2 )—C(═S)—, —N═C((O) p —R y3 )— or —N═C((S) p —R y3 )—, where the nitrogen atom in the four groups is bound to X and where p is 0 or 1,
Z is O, S or N—R z , and where
R x1 , R x2 independently of each other, are selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl,

Assignees

• Basf Se

Inventors

• Narine Arun
• Bandur Nina Gertrud
• Pickhaut Joachim
• Koller Raffael
• Von Deyn Wolfgang
• Wach Jean-Yves
• Salgado Vincent

Classifications

• C07D235/02 Primary

  condensed with carbocyclic rings or ring systems · CPC title

• A01N43/647

  Triazoles; Hydrogenated triazoles · CPC title

• A01N43/86

  six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3 · CPC title

• A01N47/20

  N-Aryl derivatives thereof · CPC title

• C07D235/06

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2 · CPC title