Insecticidal compounds

Patent metadata

Field	Value
Publication number	US-9635853-B2
Application number	US-201414782030-A
Country	US
Kind code	B2
Filing date	Apr 1, 2014
Priority date	Apr 2, 2013
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

The present invention relates to novel triazole derivatives of formula (I) having insecticidal activity, to processes and intermediates for preparing them, to insecticidal, acaricidal, nematicidal or molluscicidal compositions comprising them and to methods of using them to combat and control insect, acarine, nematode or mollusc pests wherein R 1 , R 2 , G 1 , G 2 , Q 1 and Q 2 are as defined in claim 1 ; or salts thereof.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
Q 1 is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;
Q 2 is a moiety of formula (II)

wherein
Y 1 is selected from CI, Br, I, methyl, ethyl, cyclopropyl, methoxy, difluoromethoxy, trifluoromethoxy, or methoxymethyl
Y 5 is selected from CI, Br, I, methyl, ethyl
Y 3 is heptafluoroprop-2-yl or nonafluorobut-2-yl
X is hydrogen or F
R 1 is selected from C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 alkylcarbonyl, C 1 -C 8 alkoxycarbonyl, hydroxyl, and C 1 -C 8 alkyloxy;
R 2 is selected from hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 alkylcarbonyl, C 1 -C 8 alkoxycarbonyl, hydroxyl, C 1 -C 8 alkyloxy, and aminocarbonyl-C 1 -C 4 alkylene; and
G 1 and G 2 are both oxygen;
or an agrochemically acceptable salt thereof.

2. A compound of formula (I) according to claim 1 characterized in that
Q 1 is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;
Y 1 is selected from CI, Br, I, methyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, or methoxymethyl
Y 5 is selected from CI, Br, I, ethyl
Y 3 is heptafluoroprop-2-yl or nonafluorobut-2-yl
X is hydrogen or F
R 1 is selected from C 1 -C 8 alkyl, C 2 -C 8 alkenyl;
R 2 is selected from hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl; and
G 1 and G 2 are both oxygen.

3. A compound of formula (I) according to claim 1 characterized in that
Q 1 is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;
Y 1 is selected from CI, Br, I, methyl, ethyl;
Y 5 is selected from CI, Br, I, ethyl;
Y 3 is heptafluoroprop-2-yl
X is hydrogen or F
R 1 is selected from C 2 -C 4 alkyl;
R 2 is selected from hydrogen, C 1 -C 4 alkyl; and
G 1 and G 2 are both oxygen.

4. A compound of formula (I) according to claim 1 characterized in that
Q 1 is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;
Y 1 is selected from CI, Br, methyl, ethyl;
Y 5 is selected from CI, Br, ethyl;
Y 3 is heptafluoroprop-2-yl
X is hydrogen or F
R 1 is selected from C 2 -C 4 alkyl;
R 2 is selected from hydrogen, C 1 -C 4 alkyl; and
G 1 and G 2 are both oxygen.

5. A compound of formula (I) according to claim 4 characterized in that
Q 1 is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;
Y 1 is selected from CI, Br, methyl, ethyl;
Y 5 is selected from CI, Br, ethyl;
Y 3 is heptafluoroprop-2-yl
X is F
R 1 is selected from ethyl;
R 2 is selected from hydrogen, methyl, ethyl; and
G 1 and G 2 are both oxygen.

6. A compound of formula (V)

wherein
R is selected from OH, C 1 -C 6 alkoxy, F, CI or Br;
Q 1 is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;
and the values of X and R 1 as set forth according to claim 1 , or a salt thereof.

7. A process for the production of compounds according to the formula (I) or an agrochemically acceptable salt thereof characterized in that a compound according to the formula (V)

wherein
R is selected from OH, C 1 -C 6 alkoxy, CI, F or Br
and the values of X and R 1 as set out above for the different embodiments of the present invention and Q 1 is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl is reacted with and with an amine of formula NHR 2 Q 2
wherein
Q 2 is a moiety of formula (II)

and Y 3 is heptafluoroprop-2-yl or nonafluorobut-2-yl
R 2 , Y 1 and Y 5 are as set forth according to claim 1 .

8. A method of controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in claim 1 .

9. An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in claim 1 together with an agrochemically acceptable diluent or carrier.

10. A composition according to claim 9 which further comprises one or more additional insecticidal, acaricidal, nematicidal or molluscicidal compounds.

11. A method of protecting useful plants from insects, acarines, nematodes or molluscs, comprising applying to said plants, to the locus thereof, or to plant propagation material thereof, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I in claim 1 .

Assignees

• Syngenta Participations Ag

Inventors

• Hueter Ottmar Franz
• Pitterna Thomas
• Stoller Andre
• Edmunds Andrew
• Jung Pierre Joseph Marcel

Classifications

• C07D213/82 Primary

  in position 3 · CPC title

• A01N37/22 Primary

  the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• A61P33/10

  Anthelmintics · CPC title

• C07C233/64 Primary

  having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings · CPC title