N-Thio-anthranilamid compounds and their use as pesticides

Patent metadata

Field	Value
Publication number	US-9365543-B2
Application number	US-201514739467-A
Country	US
Kind code	B2
Filing date	Jun 15, 2015
Priority date	Jul 7, 2005
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

N-Thio-anthranilamid compounds of formula (I)

wherein A is A 1

wherein the variables and the indices are as defined per the description, processes for preparing the compounds I, pesticidal compositions comprising compounds I, use of compounds I for the control of insects, acarids or nematodes, and methods for treating, controlling, preventing or protecting animals against infestation or infection by parasites by use of compounds of formula I.

First claim

We claim:

1. A compound of formula I having the following structure,

wherein,
R 1 is hydrogen; or C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, or C 3 -C 8 -cycloalkyl, each of which is unsubstituted or substituted with 1 to 5 groups independently selected from halogen, cyano, nitro, hydroxy, C 1 -C 10 -alkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 2 -C 10 -alkoxycarbonyl, C 1 -C 10 -alkylamino, di(C 1 -C 10 -alkyl)amino and C 3 -C 8 -cycloalkylamino; or C 1 -C 10 -alkylcarbonyl, C 1 -C 10 -alkoxycarbonyl C 1 -C 10 -alkylaminocarbonyl, di(C 1 -C 10 -alkyl)aminocarbonyl;
A is a group selected from A 1

wherein, # denotes the binding site, and
R 2 and R 3 each independently are R 6 , —C(═G)R 7 , —C(═NOR 7 )R 7 , —C(═NNR 7 2 )R 7 , —C(═G)OR 7 , —C(═G)NR 7 2 , —OC(═G)R 7 , —OC(═G)OR 7 , —NR 7 C(═G)R 7 , —N[C(═G)R 7 ]2, —NR 7 C(═G)OR 7 , —C(═G)NR 7 —NR 7 2 , —C(═G)NR 7 —NR 7 [C(═G)R 7 ], —NR 7 —C(═G)NR 7 2 , —NR 7 —NR 7 C(═G)R 7 , —NR 7 —N[C(═G)R 7 ] 2 , —N[(C═G)R 7 ]—NR 7 2 , —NR 7 —NR 7 [(C═G)GR 7 ], —NR 7 [(C═G)NR 7 2 , —NR 7 [C═NR 7 ]R 7 , —NR 7 (C═NR 7 )NR 7 2 , —O—NR 7 2 , —O—NR 7 (C═G)R 7 , —SO 2 NR 7 2 , —NR 7 SO 2 R 7 , —SO 2 OR 7 , —OSO2R 7 , —OR 7 , —NR 7 2 , —SR 7 , —SiR 7 3 , —PR 7 2 , —P(═G)R 7 , —SOR 7 , —SO 2 R 7 , —PG 2 R 7 2 , or —PG 3 R 7 2 ; or
R 2 and R 3 together with the sulfur atom to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, which ring can be fused with one or two saturated, partially unsaturated or unsaturated 5- to 6-membered rings which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of the above rings are unsubstituted or substituted by any combination of 1 to 6 groups R 8 ;
G is oxygen or sulfur;
R 6 is C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -cycloalkynyl, phenyl, naphthyl, biphenyl, or a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of these groups are unsubstituted or substituted by any combination of 1 to 6 groups R 8 ;
R 7 is hydrogen or R 6 ;
R 8 is R 9 ; or two groups R 8 together with the atoms to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which may contain 1 to 4 heteroatoms/heterogroups selected from oxygen, nitrogen, sulfur, SO and SO 2 , and which ring system is unsubstituted or substituted with any combination of 1 to 6 groups R 9 ;
R 9 is R 10 , R 11 , —C(═G)R 10 , —C(═NOR 10 )R 10 , —C(═NNR 10 2 )R 10 , —C(═G)OR 10 , —C(═G)NR 10 2 , —OC(═G)R 10 , —OC(═G)OR 10 , —NR 10 C(═G)R 10 , —N[C(═G)R 10 ]2, —NR 10 C(═G)OR 10 , —C(═G)NR 10 —NR 10 2 , —C(═G)NR 10 —NR 10 [C(═G)R 10 ], —NR 10 —C(═G)NR 10 2 , —NR 10 —NR 10 C(═G)R 10 , —NR 10 —N[C(═G)R 10 ] 2 , —N[(C═G)R 10 ]—NR 10 2 , —NR 10 —NR 10 [(C═G)GR 10 ], —NR 10 [(C═G)NR 10 2 , —NR 10 [C═NR 10 ]R 10 , —NR 10 (C═NR 10 )NR 10 2 , —O—NR 10 2 , —O—NR 10 (C═G)R 10 , —SO 2 NR 10 2 , —NR 10 SO 2 R 10 , —SO 2 OR 10 , —OSO2R 10 , —OR 10 , —NR 10 2 , —SR 10 , —SiR 10 3 , —PR 10 2 , —P(═G)R 10 , —SOR 10 , —SO 2 R 10 , —PG 2 R 10 2 , —PG 3 R 10 2 or two groups R 9 together are (═G), (═N—R 10 ), (═CR 10 2 ), (═CHR 10 ), or (═CH 2 );
R 10 is C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 8 -cycloalkyl, C 4 -C 8 -cycloalkenyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenyl, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl-C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkynyl-C 3 -C 8 -cycloalkyl, C 1 -C 10 -alkyl-C 4 -C 8 -cycloalkenyl, C 2 -C 10 -alkenyl-C 4 -C 8 -cycloalkenyl, C 2 -C 10 -alkynyl-C 4 -C 8 -cycloalkenyl, a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur;
wherein the above groups are unsubstituted or substituted with any combination of from 1 to 6 groups R 11 ;
R 11 is halogen, cyano, nitro, hydroxy, mercapto, amino, formyl, C 1 -C 10 -alkylcarbonyl, C 1 -C 10 -alkoxy, C 2 -C 10 -alkenyloxy, C 2 -C 10 -alkynyloxy, C 1 -C 10 -haloalkoxy, C 3 -C 10 -haloalkenyloxy, C 3 -C 10 -haloalkynyloxy, C 3 -C 8 -cycloalkoxy, C 4 -C 8 -cycloalkenyloxy, C 3 -C 8 -halocycloalkoxy, C 4 -C 8 -halocycloalkenyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkoxy, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenyloxy, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenyloxy, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkoxy, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkoxy, C 1 -C 10 -alkynyl-C 3 -C 8 -cycloalkoxy, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkenyloxy, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkenyloxy, C 1 -C 4 -alkoxy-C 2 -C 10 -alkenyloxy, mono- or di(C 1 -C 10 -alkyl)carbamoyl, mono- or di(C 1 -C 10 -haloalkyl)carbamoyl, mono- or di(C 3 -C 8 -cycloalkyl)carbamoyl, C 1 -C 10 -alkoxycarbonyl, C 3 -C 8 -cycloalkoxycarbonyl, C 1 -C 10 -alkylcarbonyloxy, C 3 -C 8 -cyclo alkylcarbonyloxy, C 1 -C 10 -haloalkoxycarbonyl, C 1 -C 10 -haloalkylcarbonyloxy, C 1 -C 10 -alkanamido, C 1 -C 10 -haloalkanamido, C 2 -C 10 -alkenamido, C 3 -C 8 -cycloalkanamido, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkanamido, C 2 -C 10 -alkenylthio, C 2 -C 10 -alkynylthio, C 1 -C 10 -haloalkylthio, C 2 -C 10 -haloalkenylthio, C 2 -C 10 -haloalkynylthio, C 3 -C 8 -cycloalkylthio, C 3 -C 8 -cycloalkenylthio, C 3 -C 8 -halocycloalkylthio, C 3 -C 8 -halocycloalkenylthio, C 3 -C 8 -cycloalkyl-C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkylthio, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenylthio, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenylthio, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkylthio, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkylthio, C 1 -C 10 -alkynyl-C 3 -C 8 -cycloalkylthio, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkenylthio, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkenylthio, C 1 -C 10 -alkylsulfinyl, C 2 -C 10 -alkenylsulfinyl, C 2 -C 10 -alkynylsulfinyl, C 1 -C 10 -haloalkylsulfinyl, C 2 -C 10 -haloalkenylsulfinyl, C 2 -C 10 -haloalkynylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkenylsulfinyl, C 3 -C 8 -halocycloalkylsulfinyl, C 3 -C 8 -halocycloalkenylsulfinyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkylsulfinyl, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkylsulfinyl, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenylsulfinyl, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenylsulfinyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 10 -alkynyl-C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkenylsulfinyl, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkenylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 2 -C 10 -alkenylsulfonyl, C 2 -C 10 -alkynylsulfonyl, C 1 -C 10 -haloalkylsulfonyl, C 2 -C 10 -haloalkenylsulfonyl, C 2 -C 10 -haloalkynylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkenylsulfonyl, C 3 -C 8 -halocycloalkylsulfonyl, C 3 -C 8 -halocycloalkenylsulfonyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkylsulfonyl, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkylsulfonyl, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenylsulfonyl, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenylsulfonyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkylsulfonyl, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkylsulfonyl, C 1 -C 10 -alkynyl-C 3 -C 8 -cycloalkylsulfonyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkenylsulfonyl, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkenylsulfonyl, C 1 -C 10 -alkylamino, C 2 -C 10 -alkenylamino, C 2 -C

Assignees

• Basf Se

Inventors

• Schmidt Thomas
• Puhl Michael
• Dickhaut Joachim
• Bastiaans Henricus Maria Martinus
• Rack Michael
• Culbertson Deborah L
• Anspaugh Douglas D
• Braun Franz-Josef
• Bucci Toni
• Cotter Henry Van Tuyl
• Kuhn David G
• Oloumi-Sadeghi Hassan

Classifications

• A61P33/00

  Antiparasitic agents · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title