Pyrazoles for controlling invertebrate pests

Patent metadata

Field	Value
Publication number	US-9955692-B2
Application number	US-201515114974-A
Country	US
Kind code	B2
Filing date	Jan 30, 2015
Priority date	Jan 31, 2014
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

The present invention relates to novel pyrazoles of formula I. Moreover, the invention relates to processes and intermediates for preparing the pyrazoles of formula I, and also to active compound combinations comprising them, to compositions comprising them, and to their use for protecting growing plants from attack or infestation by invertebrate pests. Furthermore, the invention relates to methods of applying such compounds. The present invention also relates to seed comprising such compounds.

First claim

The invention claimed is:

1. A pyrazole compound of formula I

wherein
V is O, S or NR 1a , wherein R 1a is selected from the group consisting of H, C 1 -C 10 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkylmethyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkoxy-C 1 -C 4 -alkyl, OR a , heterocyclyl, heterocyclyl-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy, or
wherein R 1a and R 4 together with the carbon atom to which R 4 is bound and the nitrogen atom to which R 1a is bound as well as the nitrogen atom between said carbon atom and said nitrogen atom form a 4- to 8-membered heterocycle, which contains the two nitrogen atoms as heteroatoms, and may further contain 1 or 2 heteroatoms which, independently of each other, are selected from the group consisting of NR B , O, and S, wherein S may be oxidized, and/or wherein the heterocycle may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from R A ;

D is selected from the group consisting of C 1 -C 8 -alkylene, C 3 -C 8 -cycloalkylene, C 3 -C 8 -heterocycloalkylene, C 2 -C 8 -alkenylene, C 3 -C 8 -cycloalkenylene, C 3 -C 8 -heterocycloalkenylene, and C 2 -C 8 -alkynylene, wherein D may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from R A ;
U is N or CR U ;
T is S, O or NR 1b , wherein R 1b is selected from the group consisting of H, C 1 -C 10 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkylmethyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkoxy-C 1 -C 4 -alkyl, OR a , heterocyclyl, heterocyclyl-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy;
R P1 , R P2 , R P3 , and R U are independently of each other selected from the group consisting of H, halogen, C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 3 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 3 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 3 -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 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
R 1 is selected from the group consisting of H, CN, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 1 -C 5 -alkylen-CN, OR a , C 1 -C 5 -alkylen-OR a , C(Y)R b , C 1 -C 5 -alkylen-C(Y)R b , C(Y)OR c , C 1 -C 5 -alkylen-C(Y)OR c , S(O) 2 R d , NR e R f , C 1 -C 5 -alkylen-NR e R f , C(Y)NR g R h , C 1 -C 5 -alkylen-C(Y)NR g R h , S(O) n NR e R f , C(Y)NR i NR e R f , C 1 -C 5 -alkylen-S(O) 2 R d , C 1 -C 5 -alkylen-S(O) n NR e R f , C 1 -C 5 -alkylen-C(Y)NR i NR e R f , phenyl, heterocyclyl, hetaryl, phenyl-C 1 -C 5 -alkyl, C 3 -C 10 -cycloalkyl-C 1 -C 5 -alkyl, heterocyclyl-C 1 -C 5 -alkyl and hetaryl-C 1 -C 5 -alkyl wherein the ring of the seven last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the radicals R y and R x ;
R 2 and R 3 are independently of each other selected from the group consisting of H, halogen, CN, NO 2 , C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl and C 2 -C 10 -alkynyl, wherein the 3 last mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1, 2 or 3 identical or different substituents R x , or wherein R 2 and R 3 are further selected from the group consisting of OR a , SR a , C(Y)R b , C(Y)OR c , S(O)R d , S(O) 2 R d , NR e R f , C(Y)NR g R h , heterocyclyl, hetaryl, C 3 -C 10 -cycloalkyl, C 5 -C 10 -cycloalkenyl and phenyl, wherein the five last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the radicals R y and R x , and wherein
R 4 is selected from the group consisting of H, C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-X, C 3 -C 6 -cycloalkyl and C 3 -C 6 -cycloalkyl-X, wherein X is selected from the group consisting of O, S, and NR B , wherein the C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from R A ; and
R 5 is selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-X, C 3 -C 6 -cycloalkyl and C 3 -C 6 -cycloalkyl-X, wherein X is selected from the group consisting of O, S, and NR B , wherein the C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from R A , or wherein
R 4 and R 5 together with the carbon atom to which they are bound form a 3- to 8-membered, saturated or unsaturated carbo- or heterocycle, which may contain 1, 2, or 3 heteroatoms which, independently of each other, are selected from the group consisting of NR B , O, and S, wherein S may be oxidized and/or wherein the carbo- or heterocycle may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from R A ;
and wherein
R A is selected from the group consisting of halogen, NO 2 , CN, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -halocycloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, S(O) n R D , ═O, ═S, ═NR C , ═NOR C , and ═NSR C ; or wherein
two R A bound to the same carbon atom or to adjacent carbon atoms together with the carbon atom(s) to which they are bound form a 3- to 6-membered, saturated or unsaturated carbo- or heterocycle, which may contain 1 or 2 heteroatoms which, independently of each other, are selected from the group consisting of NR B , O, and S, wherein S may be oxidized;
and wherein
R B is selected from the group consisting of H, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkylcarbonyl, C 1 -C 2 -haloalkylcarbonyl, and C 1 -C 2 -alkoxycarbonyl;
R C is selected from the group consisting of H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, and C 3 -C 6 -halocycloalkyl;
R D is selected from the group consisting of H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, or C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -haloalkoxy;
n is 0, 1, or 2;
Y is O or S;
R a , R b , R c are independently of each other selected from the group consisting of H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, heterocyclyl, heterocyclyl-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the ring in the six last mentioned radicals

Assignees

• Basf Se

Inventors

• Soergel Sebastian
• Saelinger Daniel
• Gockel Birgit

Classifications

• A01N25/02

  containing liquids as carriers, diluents or solvents · CPC title

• C07D403/12 Primary

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

• A01N43/58 Primary

  1,2-Diazines; Hydrogenated 1,2-diazines · CPC title

• A01N25/08

  containing solids as carriers or diluents · CPC title

• C07D401/12

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