Pesticidally active semi-carbazones and thiosemicarbazones derivatives

Patent metadata

Field	Value
Publication number	US-10721933-B2
Application number	US-201615544272-A
Country	US
Kind code	B2
Filing date	Jan 19, 2016
Priority date	Jan 23, 2015
Publication date	Jul 28, 2020
Grant date	Jul 28, 2020

Abstract

Compounds of formula (I), wherein the substituents are as defined in claim 1 , and agrochemically acceptable salts and enantiomers thereof, can be used as insecticides.

First claim

The invention claimed is:

1. A compound of formula I,

wherein,
Ar 1 is phenyl or phenyl substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 3 haloalkyl-C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfoximino, C 2 -C 4 alkylcarbonyl, CHO, C 2 -C 6 alkoxycarbonyl, or C 2 -C 6 haloalkoxycarbonyl;
Ar 2 is phenyl or phenyl substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 3 haloalkyl-C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfoximino, C 2 -C 4 alkylcarbonyl, CHO, C 2 -C 6 alkoxycarbonyl, or C 2 -C 6 haloalkoxycarbonyl;
X is a direct bond, O, S, SO 2 , CR 4 R 5 or NR 6 ;
Y is oxygen or sulfur;
R 1 is hydrogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 3 -alkoxy;
R 2 and R 3 are independently from each other hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, halo-C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 6 dialkylaminocarbonyl, C 2 -C 6 alkoxycarbonyloxy, C 2 -C 6 alkylaminocarbonyloxy, C 3 -C 6 dialkylaminocarbonyloxy, or C 1 -C 4 alkoxyimino-C 1 -C 4 alkyl; provided that when R 2 and R 3 are different from hydrogen, R 2 and R 3 can be substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfoximino, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino, C 3 -C 6 cycloalkylamino, C 1 -C 4 alkyl-C 3 -C 6 cycloalkylamino, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, and C 2 -C 8 dialkylaminocarbonyl;
R 4 , R 5 and R 6 are independently from each other hydrogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 3 -alkoxy;
J is a group selected from:

R 9a and R 7a are independently selected from hydrogen, halogen, nitro, cyano, hydroxy, ═O, CHO, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfoximino-C 1 -C 4 alkyl, C 1 -C 4 alkylamino, C 2 -C 4 dialkylamino, C 3 -C 6 cycloalkylamino, C 1 -C 6 alkyl-C 3 -C 6 cycloalkylamino, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 6 dialkylaminocarbonyl, C 2 -C 6 alkoxycarbonyloxy, C 2 -C 6 alkylaminocarbonyloxy, C 3 -C 6 dialkylaminocarbonyloxy, C 1 -C 4 alkoxyimino-C 1 -C 4 alkyl-CONHSO 2 —C 1 -C 6 -alkyl, —CONHSO 2 N(C 1 -C 6 -alkyl) 2 , or C 3 -C 6 trialkylsilyl; or an agrochemically acceptable salt, stereoisomer, and N-oxide of the compounds of formula I.

2. The compound of claim 1 , wherein:
Ar 1 is phenyl or phenyl substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 3 haloalkyl-C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfoximino, C 2 -C 4 alkylcarbonyl, CHO, C 2 -C 6 alkoxycarbonyl, or C 2 -C 6 haloalkoxycarbonyl;
Ar 2 is phenyl or phenyl substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 3 haloalkyl-C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfoximino, C 2 -C 4 alkylcarbonyl, CHO, C 2 -C 6 alkoxycarbonyl, or C 2 -C 6 haloalkoxycarbonyl;
X is a direct bond, O, S, SO 2 , CR 4 R 5 , or NR 6 ;
Y is oxygen or sulfur;
R 1 is hydrogen, or C 1 -C 6 -alkyl, R 2 and R 3 are independently from each other hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, halo-C 3 -C 6 -cycloalkyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 6 dialkylaminocarbonyl, C 2 -C 6 alkoxycarbonyloxy, C 2 -C 6 alkylaminocarbonyloxy, C 3 -C 6 dialkylaminocarbonyloxy, provided that when R 2 and R 3 groups are different from hydrogen, said R 2 and R 3 groups can be substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 3 -C 6 halocycloalkyl, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, and C 1 -C 4 alkylthio;
R 4 , R 5 and R 6 are independently from each other hydrogen or C 1 -C 6 -alkyl;
J is a group selected from:

wherein R 9a and R 7a are independently selected from C 1 -C 6 alkyl or C 1 -C 6 haloalkyl.

3. The compound of claim 1 , wherein:
Ar 1 is phenyl or phenyl substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 3 haloalkyl-C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfoximino, C 2 -C 4 alkylcarbonyl, CHO, C 2 -C 6 alkoxycarbonyl, or C 2 -C 6 haloalkoxycarbonyl;
Ar 2 is phenyl or phenyl substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 3 haloalkyl-C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfoximino, C 2 -C 4 alkylcarbonyl, CHO, C 2 -C 6 alkoxycarbonyl, or C 2 -C 6 haloalkoxycarbonyl;
X is a direct bond, or O;
Y is oxygen or sulfur;
R 1 is hydrogen, or C 1 -C 6 -alkyl, R 2 and R 3 are independe

Assignees

• Syngenta Participations Ag

Inventors

• Jeanguenat Andre
• Benfatti Fides
• Pitterna Thomas

Classifications

• C07D487/00

  Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 · CPC title

• C07D209/48

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title

• C07D209/50

  with oxygen and nitrogen atoms in positions 1 and 3 · CPC title

• C07D277/66

  with aromatic rings or ring systems directly attached in position 2 · CPC title

• C07D231/56

  Benzopyrazoles; Hydrogenated benzopyrazoles · CPC title