Compounds for controlling arthropods

Patent metadata

Field	Value
Publication number	US-10357036-B2
Application number	US-201615751515-A
Country	US
Kind code	B2
Filing date	Aug 11, 2016
Priority date	Aug 13, 2015
Publication date	Jul 23, 2019
Grant date	Jul 23, 2019

Abstract

The invention relates inter alia to compounds of the general formula (I). Also described are methods for preparing the compounds of the formula (I). The compounds according to the invention are especially suitable for controlling insects, arachnids and nematodes in agriculture, and ectoparasites in veterinary medicine and also as herbicides.

First claim

What is claimed is:

1. Compound of formula (I′)

in which
U is —C(═W)-Q or —S(O) 2 -Q,
R 1 is H, in each case optionally substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl(C 1 -C 3 )-alkyl, heteroaryl(C 1 -C 3 )-alkyl, or
R 1 is H, in each case optionally substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 3 -C 7 -cycloalkyl(C 1 -C 3 )-alkyl, aryl(C 1 -C 3 )-alkyl, heteroaryl(C 1 -C 3 )-alkyl,
the moieties are as follows:
A 1 is CR 2 or N,
A 2 is CR 3 or N,
A 3 is CR 4 or N,
A 4 is CR 5 or N,
A 5 is C,
B 1 is CR 6 or N,
B 2 is CR 7 or N,
B 3 is CR 8 or N,
B 4 is CR 9 or N, and
B 5 is CR 10 or N,
but not more than three of the A 1 to A 4 moieties are N and not more than three of the B 1 to B 5 moieties are simultaneously N;
M 1 , M 2 are each independently H, in each case optionally substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl(C 1 -C 3 )-alkyl, heteroaryl(C 1 -C 3 )-alkyl, or
M 1 and M 2 with the carbon atom to which they are attached form an optionally substituted 3-, 4-, 5- or 6-membered ring which optionally contains 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or 0, 1 or 2 sulfur atoms, or
M 1 or M 2 with R 4 from A 3 , the carbon atom of A 3 , and As and D form a 5- or 6-membered ring optionally substituted by F, Cl, Br, I, C 1 -C 3 -alkyl, which may contain 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or 0, 1 or 2 sulfur atoms,
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 9 and R 10 are each independently H, halogen, cyano, nitro, in each case optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkoxyimino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, N—C 1 -C 6 -alkylamino or N,N-di-C 1 -C 6 -alkylamino,
if neither of the A 2 and A 3 moieties is N, R 3 and R 4 together with the carbon atom to which they are attached may form a 5- or 6-membered ring containing 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulfur atom, or
if neither of the A 1 and A 2 moieties is N, R 2 and R 3 together with the carbon atom to which they are attached may form a 6-membered ring containing 0, 1 or 2 nitrogen atoms;

R 8 is halogen, cyano, nitro, in each case optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkoxyimino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, N—C 1 -C 6 -alkylamino or N,N-di-C 1 -C 6 -alkylamino;
W is O or S,
Q is C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl in each case optionally independently substituted by halogen, cyano; or 6-membered aromatic ring selected from phenyl or pyridyl optionally independently substituted by halogen, cyano;
T is one of the 5-membered heteroaromatic systems T2, T3, or T7 shown below, where the bond to the ring (C—B1-B2-B3-B4-B5) is indicated by an asterisk,

where R 11 is independently H, optionally halogenated C 1 -C 6 -alkyl or halogen,
and/or a salt, N-oxide and/or tautomeric form of a compound of the formula (I′).

2. Compound according to claim 1 , wherein in T is H.

3. Compound according to claim 1 , wherein T is T3.

4. Compound according to claim 1 , wherein A 1 is CR 2 , A 2 is CR 3 , A 3 is CR 4 , A 4 is CR 5 , As is C and R 2 , R 3 and R 5 are in each case H.

5. Compound according to claim 1 , wherein B 1 is CR 6 , B 2 is CR 7 , B 3 is CR 8 , B 4 is CR 9 and B 5 is CR 10 .

6. Compound according to claim 1 , wherein B 3 is CR 8 and R 8 is halogenated C 1 -C 6 -alkyl and B 2 is CR 7 and B 4 is CR 9 and R 7 and R 9 are each H.

7. Compound according to claim 1 , wherein B 1 is CR 6 and B 5 is CR 10 and R 6 and R 10 are each optionally independently halogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkyl substituted by halogen, C 1 -C 6 -alkoxy or C 1 -C 6 -alkoxy substituted by halogen.

8. Compound according to claim 1 , wherein A 3 is CR 4 and R 4 is H, halogen, or R 4 together with the carbon atom of CR 4 , As and either C-M 1 or C-M 2 form a 5- or 6-membered ring optionally substituted by F, Cl, Br, I, C 1 -C 3 -alkyl, which may contain 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or 0, 1 or 2 sulfur atoms.

9. Compound according to claim 1 , wherein M 1 and M 2 are each independently H or C 1 -C 6 -alkyl, or C-M 1 or C-M 2 together with CR 4 and As form a 5- or 6-membered ring optionally substituted by F, Cl, Br, I, C 1 -C 3 -alkyl, which may contain 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or 0, 1 or 2 sulfur atoms.

10. Compound according to claim 1 , wherein R 1 is H and W is O.

11. Compound according to claim 1 , wherein R 4 is H, F or Cl or R 4 together with the carbon atom of CR 4 , A 5 and either C-M 1 or C-M 2 form a 5-membered ring optionally substituted by F, Cl, Br, I, C 1 -C 3 -alkyl, which may contain 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or 0, 1 or 2 sulfur atoms.

12. Compound according to claim 1 , wherein M 1 and M 2 are each independently H or C-M 1 or C-M 2 together with CR 4 and As form a 5-membered ring optionally substituted by F, Cl, Br, I, C 1 -C 3 -alkyl, which may contain 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or 0, 1 or 2 sulfur atoms.

13. A composition comprising at least one compound according to claim 1 and an extender and/or a surface-active substance.

14. The composition of claim 13 , further comprising a fungicide, bactericide, acaricide, molluscicide, nematicide, insecticide, microbiological agent, beneficial organism, herbicide, herbicide, fertilizer, bird repellant, phytotonics, sterilant, safener, semiochemcical, and/or plant growth regulator.

15. A method for protecting transgenic or conventional seed and the plant that arises therefrom from infestation by pests comprising treating seed with at least one compound according to claim 1 .

16. A product method of controlling a pest comprising applying a compound according to claim 1 to the pest and/or its habitat.

17. The method according to claim 16 , wherein the pest is an insect, arachnid, helminth, nematode, or mollusc.

18. Seed in which a compound according to claim 1 has been applied to the seed as a constituent of a coating or as a further layer or further layers in addition to a coating.

19. A method of controlling a parasite in an animal comprising administering the compound of claim 1 to the animal.

Assignees

• Bayer Cropscience Ag

Inventors

• Harschneck Tobias
• Maue Michael
• Hallenbach Werner
• Arlt Alexander
• Velten Robert
• Fischer Reiner
• Schwarz Hans-Georg
• Görgens Ulrich
• Ilg Kerstin
• Raming Klaus
• Horstmann Sebastian
• Portz Daniela
• Köbberling Johannes
• Turberg Andreas
• Dietrich Hansjörg

Classifications

• C07D231/10 Primary

  having two or three double bonds between ring members or between ring members and non-ring members · CPC title

• C07D249/06

  with aryl radicals directly attached to ring atoms · CPC title

• C07D231/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• A01N43/50

  1,3-Diazoles; Hydrogenated 1,3-diazoles · CPC title

• C07D401/12

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