Pesticide compounds

Patent metadata

Field	Value
Publication number	US-9497970-B2
Application number	US-201414903887-A
Country	US
Kind code	B2
Filing date	Jul 14, 2014
Priority date	Jul 15, 2013
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

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

We claim:

1. 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, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1

Assignees

• Basf Se

Inventors

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

Classifications

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D231/56

  Benzopyrazoles; Hydrogenated benzopyrazoles · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D275/04

  condensed with carbocyclic rings or ring systems · CPC title

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title