Insecticidal compounds

Patent metadata

Field	Value
Publication number	US-RE49022-E
Application number	US-201416560794-A
Country	US
Kind code	E1
Filing date	Dec 19, 2014
Priority date	Dec 23, 2013
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

Abstract

The present invention relates to novel bisamide 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 X 0 , X 1 , X 2 , Y 1 , Y 2 , R 1 , R 2 , G 1 and G 2 , and Q are as described in formula 1 or salts and n-Oxides thereof.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
X 0 is bromo, chloro or hydrogen;
X 1 is methoxy; and X 2 is hydrogen;, or
X 1 is hydrogen and X 2 is cyano;
Y 1 and Y 2 are independently of each other chloro, bromo, iodo, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, and or C 1 -C 4 haloalkoxy;
R 1 and R 2 are independent independently of one another 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 or aminocarbonyl-C 1 -C 4 alkylene;
G 1 and G 2 are independent independently of each other oxygen or sulfur;
Q is a group selected from Q1, Q2, Q3, Q4 and Q5, where
Q1 is a group of formula (IIa)

where the substituents W1 are independently selected from halogen, cyano, and C 1 alkyl, and n1 is 2,
Q2 is a group of formula (IIb)

where W 2 is selected from, hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy,
Q3 is a group of formula (IIc)

where W 3 is selected from, hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy,
Q4 is a group of formula (IId)

where W 4 is selected, from hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy,
Q5 is a group of formula (IIe)

where W 5 is selected from hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C4 alkoxy or C 1 -C 4 haloalkoxy.

2. A The compound of formula (I) according to claim 1 wherein Y 1 and Y 2 are selected from Cl, Br, I, methyl, ethyl, methoxy, difluoromethoxy, and trifluoromethoxy,;
X 0 is hydrogen or Br, bromo, or Cl chloro;
R 1 is selected from hydrogen or C 1 -C 2 alkyl;
R 2 is selected from hydrogen, C 1 -C 2 alkyl;
and
G 1 and G 2 are both oxygen.

3. A compound of formula (III)

wherein X 0 , Y 1 , Y 2 , X 1 , X 2 , R 1 , and R 2 are as defined in formula (I) of claim 1
X 0 is bromo, chloro or hydrogen;
X 1 is methoxy and X 2 is hydrogen, or
X 1 is hydrogen and X 2 is cyano;
Y 1 and Y 2 are independently of each other chloro, bromo, iodo, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkoxy;
R 1 and R 2 are independently of one another 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, or aminocarbonyl-C 1 -C 4 alkylene; and
G 2 is oxygen or sulfur.

4. 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 .

5. 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.

6. A composition according to claim 5 which further comprises one or more additional insecticidal, acaricidal, nematicidal or molluscicidal compounds.

7. 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 .

8. The compound of formula (I) according to claim 1 wherein Q is Q1.

9. The compound of formula (I) according to claim 8 wherein Q1 is a group of formula (IIa)

where the substituents W1 are independently selected from, cyano and C 1 alkyl, and n1 is 2.

10. The compound of formula (I) according to claim 9 wherein X 1 is hydrogen and X 2 is cyano.

11. The compound of formula (I) according to claim 8 wherein X 1 is hydrogen and X 2 is cyano.

12. The compound of formula (I) according to claim 1 wherein Q is Q2.

13. The compound of formula (I) according to claim 1 wherein Q is Q3.

14. The compound of formula (I) according to claim 1 wherein Q is Q4.

15. The compound of formula (I) according to claim 1 wherein Q is Q5.

16. The compound of formula (I) according to claim 1 wherein Y 1 and Y 2 are selected from chloro, bromo, ethyl, methoxy and difluoromethoxy.

17. The compound of formula (I) according to claim 1 wherein X 0 is bromo or chloro.

18. The compound of formula (I) according to claim 1 wherein X 0 is bromo.

19. A compound selected from

20. The compound of claim 19, wherein the compound is

21. The compound of claim 19, wherein the compound is

22. The compound of claim 19, wherein the compound is

Assignees

• Syngenta Participations Ag

Inventors

• Edmunds Andrew
• Stoller Andre
• Pitterna Thomas

Classifications

• C07C255/57 Primary

  containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton · CPC title

• A01N43/40 Primary

  six-membered rings · CPC title

• A01N27/00

  Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons · CPC title

• C07C255/56

  containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton · CPC title

• A01N37/34 Primary

  Nitriles · CPC title