N-thio-anthranilamide compounds and their use as pesticides

Patent metadata

Field	Value
Publication number	US-9533968-B2
Application number	US-201314402509-A
Country	US
Kind code	B2
Filing date	May 7, 2013
Priority date	May 24, 2012
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

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

wherein the substituents are as defined in the description.

The present invention further relates to a method for combating or controlling invertebrate pests, to a method for protecting plant propagation material and/or the plants which grow therefrom, to plant propagation material comprising at least one compound according to the present invention, to a method for treating or protecting an animal from infestation or infection by parasites, to a process for the preparation of a composition for treating infested or infected animals and/or for protecting animals against infestation or infection by parasites, and to a compound according to the invention for use as a medicament.

First claim

We claim:

1. A compound of formula (I-A)

wherein
R 1a and R 1b are independently selected from the group consisting of halogen; cyano; azido; nitro; —SCN; SF 5 ; C 1 -C 6 -alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 7 ; C 3 -C 8 -cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 7 ; C 2 -C 6 -alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 7 ; C 2 -C 6 -alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 7 ; —Si(R 14 ) 2 R 13 ; —OR 8 ; —OS(O) n R 8 ; —SR 8 ; —S(O) m R 8 ; —S(O) n N(R 9a )R 9b ; —N(R 9a )R 9b ; —N(R 9a )C(═O)R 7 ; C(═O)R 7 ; —C(═O)OR 8 ; —C(═NR 9a )H; —C(═NR 9a )R 7 ; —C(═O)N(R 9a )R 9b ; C(═S)N(R 9a )R 9b ; and phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R 10 ;
R 3 is selected from the group consisting of chloro, bromo, iodo, CF 3 , CHF 2 , OCH 3 , and OCHF 2 ;
R 4 is selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF 5 , C 1 -C 6 -alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 7 , C 3 -C 8 -cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 7 , C 2 -C 6 -alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 7 , C 2 -C 6 -alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 7 , —Si(R 14 ) 2 R 13 , —OR 8 , —OS(O) n R 8 , —SR 8 , —S(O) m R 8 , —S(O) n N(R 9a )R 9b , —N(R 9a )R 9b , N(R 9a )C(═O)R 7 , —C(═O)R 7 , —C(═O)OR 8 , —C(═S)R 7 , —C(═S)OR 8 , —C(═NR 9a )R 7 , —C(═O)N(R 9a )R 9n , —C(═S)N(R 9a )R 9b , and phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R 10 ;
R 5 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl (sec-butyl), isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, and cyclobutylpropyl;
each R 7 is independently selected from the group consisting of cyano, azido, nitro, —SCN, SF 5 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(R 14 ) 2 R 13 , —OR 8 , —OSO 2 R 8 , —SR 8 , —S(O) m R 8 , —S(O) n N(R 9a )R 9b , —S(═O)(═NH)—R 8 , —S(═O)(═N—CN)—R 8 , —N(R 9a )R 9b , —C(═O)N(R 9a )R 9b , —C(═S)N(R 9a )R 9b , —C(═O)OR 8 , —C(═O)R 19 , and phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R 10 ;
and, in case R 7 is bound to a cycloalkyl group, R 7 may additionally be selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl and benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R 10 ;
and in groups —C(═O)R 7 , —C(═S)R 7 , —C(═NR 9a )R 7 , —C(═N-QR 8 )R 7 and —N(R 9a )C(═O)R 7 , R 7 may additionally be selected from hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl and benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R 10 ;
or two geminally bound radicals R 7 together form a group selected from ═CR 11 R 12 ; ═S(R 8 ) 2 , ═NR 9a , ═NOR 8 and ═NNR 9a R 9b ;
each R 8 is independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, —Si(R 14 ) 2 R 13 , —SR 20 , —S(O) m R 20 , —S(O) n N(R 9a )R 9b ,
—N(R 9a )R 9b , —N═CR 15 R 16 , —C(═O)R 17 , —C(═O)N(R 9a )R 9b , —C(═S)N(R 9a )R 9b , —C(═O)OR 20 , and phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R 10 ;

with the proviso that R 8 is not C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy if it is bound to an oxygen atom;
R 9a , R 9b are, independently of each other and independently of each occurrence, selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 19 , C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by one or more radicals R 19 , C 3 -C 8 -cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 19 , C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by one or more radicals R 19 , C 2 -C 6 -alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 19 , C 2 -C 6 -alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 19 , —N(R 21 )R 22 ; —N(R 21 )C(═O)R 19 ; —Si(R 14 ) 2 R 13 ; —OR 20 ; —SR 20 ; —S(O) m R 20 ; —S(O) n N(R 21 )R 22 ; —C(═O)R 19 ; —C(═O)OR 20 , —C(═O)N(R 21 )R 22 ; —C(═S)R 17 ; —C(═S)OR 20 , —C(═S)N(R 21 )R 22 ; —C(═NR 21 )R 17 —S(O) m R 20 , —S(O) n N(R 21 )R 22 , phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R 10 ,
or R 9a and R 9b together form a group ═CR 11 R 12 or ═S(R 8 ) 2 ;
each R 10 is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF 5 , C 1 -C 10 -alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 19 , C 3 -C 8 -cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 19 , C 2 -C 10 -alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 19 , C 2 -C 10 -alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 19 , —Si(R 14 ) 2 R 13 , —OR 20 , —OS(O) n R 20 , —SR 20 , —S(O) m R 20 , —S(O) n N(R 21 )R 22 , —N(R 21 )R 22 , C(═O)R 19 , —C(═O)OR 20 , —c(═NR 21 )R 22 , —C(═O)N(R 21 )R 22 , —C(═S)N(R 21 )R 22 , phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy;
R 11 , R 12 are, independently of each other and independently of each occurrence, selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy,
—C(═O)R 19 , —C(═O)OR 20 , —C(═NR 21 )R 22 , —C(═O)N(R 21 )R 22 , —C(═S)N(R 21 )R 22 , and phenyl which may be substituted by 1, 2, 3, 4, or 5 radicals R 10 ;

with the proviso that R 11 , R 12 are not selected from —C(═O)R 19 if bound as two geminal R 19 radicals;
R 13 , R 14 are, independently of each other and independently of each occurrence, selected from the group consisting of C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl and benzyl;
R 15 , R 16 are, independently of each other and independently of each occurrence, selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6

Assignees

• Basf Se

Inventors

• Körber Karsten
• Wach Jean-Yves
• Kaiser Florian
• Von Deyn Wolfgang
• Bandur Nina Gertrud
• Dickhaut Joachim
• Narine Arun
• Culbertson Deborah L
• Neese Paul
• Gunjima Koshi
• David Michael
• Braun Franz Josef

Classifications

• A61P33/00

  Antiparasitic agents · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/10

  Anthelmintics · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• A61K31/4439

  containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465) · CPC title