Azoline compounds

Patent metadata

Field	Value
Publication number	US-9968087-B2
Application number	US-201515121493-A
Country	US
Kind code	B2
Filing date	Feb 25, 2015
Priority date	Feb 26, 2014
Publication date	May 15, 2018
Grant date	May 15, 2018

Abstract

The present invention relates to azoline compounds of formula I

wherein A, B 1 , B 2 , B 3 , G 1 , G 2 , X 1 , R 1 , R 3a , R 3b , R g1 and R g2 are as defined in the claims and the description. The compounds 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. An azoline compound of the formula I

wherein
X 1 is O or CH 2 ;
A is a group of following formula:

wherein
# denotes the bond to the aromatic ring of formula (I);
W is selected from O and S;
Y is selected from hydrogen, —N(R 5 )R 6 and —OR 9 ;

B 1 , B 2 and B 3 are each independently CR 2 ;
G 1 and G 2 are each independently CR 4 ;
R g1 and R g2 form together a bridging group selected from —CH 2 CH 2 CH 2 CH 2 — and —CH 2 CH 2 CH 2 —;
R 1 is CF 3 ;
each R 2 is independently selected from the group consisting of hydrogen, halogen, C 1 -C 2 -haloalkoxy and C 1 -C 2 -haloalkyl;
R 3a , R 3b are each independently selected from the group consisting of hydrogen, halogen, hydroxyl, —CO 2 R 3d , C 2 -C 3 -alkenyl, C 2 -C 3 -alkynyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -haloalkylthio, C 1 -C 3 -alkylsulfonyl and C 1 -C 3 -haloalkylsulfonyl; or
R 3a and R 3b together form a group ═O, ═C(R 3c ) 2 , ═NOH or ═NOCH 3 ;

each R 3c is independently selected from the group consisting of hydrogen, halogen, CH 3 and CF 3 ;
R 3d is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl and C 1 -C 3 -alkyloxy-C 1 -C 3 -alkyl-;
each R 4 is independently selected from the group consisting of hydrogen, halogen and cyano;
R 5 selected from hydrogen, C 1 -C 6 -alkyl, C 2 -C 3 -alkynyl and CH 2 —CN;
R 6 is selected from hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkyl which carries one radical R 8 , C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl;
—N(R 101a )R 101b ,

wherein
R 101a is selected from hydrogen and C 1 -C 6 -alkyl; and
R 101b is selected from hydrogen, —C(═O)N(R 14a )R 14b , wherein
R 14a is selected from the group consisting of hydrogen and C 1 -C 6 -alkyl; and
R 14b is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkynyl, CH 2 —CN, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy;
phenyl, optionally 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

where in these rings E-1 to E-42 as a meaning for R 101b
the zigzag line denotes the attachment point to the remainder of the molecule;
k is 0, 1, 2 or 3, and

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 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 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl and di-(C 1 -C 4 -alkyl)aminocarbonyl;

—CH═NOR 9a , wherein R 9a is selected from hydrogen, C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl;
phenyl which may be substituted with 1, 2, 3, 4, or 5 substituents R 11 , and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO 2 , as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R 11 ; wherein
each R 11 is independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, 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; or
two R 11 present on the same carbon atom of a saturated heterocyclic ring may form together ═O or ═S; or
two R 11 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 ;

each R 8 is independently selected from OH, CN, C 3 -C 8 -cycloalkyl which optionally carries a CN or a C 1 -C 2 -haloalkyl substituent; C 3 -C 8 -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 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —C(═O)N(R 102a )R 102b , phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R 16 , and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO 2 , as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R 16 ;
wherein
R 102a is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 3 -alkynyl and CH 2 —CN;
R 102b is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, CH 2 —CN, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, phenyl which is optionally substituted with 1, 2, 3, 4 or 5 substituents selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, 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 and C 1 -C 4 -haloalkylthio; and a heterocyclic ring selected from rings of formulae E-1 to E-42 as defined above and E-43 to E-57:

where in these rings E-43 to E-57
the zigzag line denotes the attachment point to the remainder of the molecule;
k is 0, 1, 2 or 3,

n is 0, 1 or 2; and
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 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 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, 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; and

each R 16 as a substituent on phenyl (as a meaning of R 8 ) or the heterocyclic rings (as a meaning of R 8 ) is independently selected fro

Assignees

• Basf Se

Inventors

• Bindschaedler Pascal
• Von Deyn Wolfgang

Classifications

• A61P33/00

  Antiparasitic agents · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• C07D413/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/40

  six-membered rings · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title