Azoline compounds substituted by a carbocyclic condensed ring system

Patent metadata

Field	Value
Publication number	US-10085448-B2
Application number	US-201515539009-A
Country	US
Kind code	B2
Filing date	Dec 21, 2015
Priority date	Dec 22, 2014
Publication date	Oct 2, 2018
Grant date	Oct 2, 2018

Abstract

Compounds of formula (I)

as defined herein are provided. Uses of these compounds for controlling invertebrate pests, protecting plant propagation material and providing an agricultural and a veterinary composition including the compounds are also described. Compounds for use as intermediate compounds in the preparation of compounds I are also described.

First claim

We claim:

1. Azoline compounds of the formula I

wherein:
X 1 is selected from O and CH 2 ;
A is a group selected from A 1 , A 2 and A 3 ;
wherein
A 1 is a group —C(R 7a )(R 7b )—N(R 51 )—C(═O)—R 61 ;
A 2 is a group —CH(═NNH—C(O)—NH—R 62 ); and
A 3 is a heterocyclic ring selected from heterocyclic rings of formulae D-1 to D-66:

wherein a zigzag line in the heterocyclic rings of formulae D-1 to D-66 denotes an attachment point to a remainder of the azoline compound;
k is one of 0, 1, 2 and 3; and
each R 11 is independently selected from the group consisting of halogen, cyano, nitro, 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, C 1 -C 4 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl and C 2 -C 4 -haloalkynyl;

B 1 , B 2 , B 3 , B 4 and B 5 are independently selected from a group consisting of N and CR 2 , wherein zero or one of B 1 , B 2 , B 3 , B 4 and B 5 is N;
R g1 and R g2 form together a bridging group selected from —CH 2 CH 2 CH 2 — and —CH 2 CH 2 CH 2 CH 2 —;
R 1 is C 1 -haloalkyl;
each R 2 is independently selected from a group consisting of hydrogen, halogen, C 1 -C 2 -haloalkoxy and C 1 -C 2 -haloalkyl;
R 3a and R 3b are independently selected from hydrogen and halogen;
R 7a and R 7b are independently selected from hydrogen, cyano, methyl and C 1 -haloalkyl;
R 51 is selected from a group consisting of hydrogen, C 1 -C 3 -alkyl, C 2 -C 3 -alkenyl, C 2 -C 3 -alkynyl, C 1 -C 3 -alkoxymethyl and CH 2 —CN;
R 61 is selected from a group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyl substituted by one or two radicals R 81 , C 1 -C 6 -haloalkyl which carries one radical R 81 , C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl which carries a CN substituent, C 3 -C 6 -halocycloalkyl, —N(R 101a )R 101b , —C(═O)N(R 111a )R 111b ,
—CH═NOR 91 , phenyl, phenyl which is substituted with 1, 2, 3, 4, or 5 substituents R 16 and a heterocyclic ring selected from rings of formulae E-1 to E-63:

wherein
a zigzag line in the rings of formulae E-1 to E-63 denotes an attachment point to a remainder of the azoline compound,
k is one of 0, 1, 2 and 3,
n is one of 0, 1 and 2, and
R 16 is as defined below;

R 62 is selected from a group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 3 -C 5 -cycloalkyl, C 3 -C 5 -halocycloalkyl, C 3 -C 5 -cycloalkyl-methyl-, C 3 -C 5 -cycloalkyl substituted with a CN group, C 1 -C 4 -alkyl substituted with a CN group, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy;
each R 81 is independently selected from OH, CN, C 3 -C 6 -cycloalkyl C 3 -C 6 -cycloalkyl which carries a CN substituent, C 3 -C 6 -cycloalkyl which carries a C 1 -haloalkyl substituent, C 3 -C 6 -halocycloalkyl, 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(═O)N(R 101c )R 101d , phenyl, phenyl substituted with 1, 2, 3, 4, or 5 substituents R 16 , and the heterocyclic ring selected from the rings of formulae E-1 to E-63;
R 91 is selected from hydrogen, C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl;
R 101a , R 101c and R 111a are independently selected from hydrogen and C 1 -C 6 -alkyl;
R 101b is selected from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, CH 2 —CN, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkylmethyl, phenyl, phenyl substituted with 1, 2, 3, 4, or 5 substituents R 16 ; and a heterocyclic ring selected from rings of formulae E-1 to E-42 as defined above;
R 101d and R 111b are independently selected from hydrogen, 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 6 -cycloalkyl C 3 -C 6 -cycloalkyl which carries a CN substituent, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkylmethyl and C 3 -C 6 -halocycloalkylmethyl;
each R 16 is independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl and di-(C 1 -C 4 -alkyl)aminocarbonyl; or
two R 16 present on the same carbon atom of a saturated ring may form together ═O or ═S; or
two R 16 present on the same S or SO ring member of a heterocyclic ring may together form a group ═N(C 1 -C 6 -alkyl), ═NO(C 1 -C 6 -alkyl), ═NN(H)(C 1 -C 6 -alkyl) or ═NN(C 1 -C 6 -alkyl) 2 ;

and at least one of the N-oxides, stereoisomers and agriculturally or veterinarily acceptable salts thereof.

2. The compounds as claimed in claim 1 , where X 1 is O.

3. The compounds as claimed in claim 1 , where X 1 is CH 2 .

4. The compounds as claimed in claim 1 , wherein A is the group A 1 ,
R 7a is hydrogen;
R 7b is selected from hydrogen, CH 3 , CF 3 and CN;
R 51 is selected from hydrogen and C 1 -C 3 -alkyl; and
R 61 is selected from C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 4 -alkyl substituted by one radical R 81 , C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl which carries a CN substituent, C 3 -C 6 -halocycloalkyl, phenyl, phenyl which is substituted with 1, 2, 3, 4, or 5 substituents R 16 ; and the heterocyclic ring selected from the rings of formulae E-1 to E-63;
R 81 is selected from CN, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl which carries a CN or a CF 3 substituent, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkyl

Assignees

• Basf Se

Inventors

• Bindschaedler Pascal
• Datta Gopal Krishna
• Von Deyn Wolfgang
• Braun Franz-Josef

Classifications

• A01N47/34

  containing the groups [IMAGE cpc-sch-A01N-0947.gif], e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products · CPC title

• C07D261/04

  having one double bond between ring members or between a ring member and a non-ring member · CPC title

• C07D207/20 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• A01N43/80

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

• A01N43/36 Primary

  five-membered rings · CPC title