Compounds for controlling arthropods

Patent metadata

Field	Value
Publication number	US-9758485-B2
Application number	US-201415033415-A
Country	US
Kind code	B2
Filing date	Nov 5, 2014
Priority date	Nov 5, 2013
Publication date	Sep 12, 2017
Grant date	Sep 12, 2017

Abstract

The invention relates inter alia to compounds of the general formula (I)

in which the A 1 -A 4 , T, n, W, Q, R 1 and B 1 -B 4 radicals are each as defined in the description. Also described are processes for preparing the compounds of the formula (I). The inventive compounds are especially suitable for controlling insects, arachnids and nematodes in agriculture, and ectoparasites in veterinary medicine.

First claim

The invention claimed is:

1. A compound of formula (Ia″)

wherein
D 1 is C—R 11 or a heteroatom selected from N and O;
D 2 is C—R 11 or a heteroatom selected from N and O;
D 3 is C or N;
D 4 is C or N;
D 5 is C—R 11 or N;
where not more than one (1) or two moieties selected from D 1 , D 2 , D 3 , D 4 and D 5 are a heteroatom;

is an aromatic system; and
R 1 is H, in each case optionally substituted 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, or heteroaryl(C 1 -C 3 )-alkyl;
the following 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,
B 1 is CR 6 or N,
B 2 is CR 7 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 one moiety selected from B 1 , B 2 , B 4 , and B 5 is N;
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 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino, N,N-di-C 1 -C 6 -alkylamino or N—C 1 -C 3 -alkoxy-C 1 -C 4 -alkylamino or 1-pyrrolidinyl; wherein R 6 and R 10 are not both H,
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 bonded 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 sulphur 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 bonded may form a 6-membered ring containing 0, 1 or 2 nitrogen atoms;

R 8 is fluorine-substituted C 1 -C 4 -alkoxy or fluorine-substituted C 1 -C 4 -alkyl;
R 11 is independently H;
W is O or S;
Q is H, formyl, hydroxyl, amino or in each case optionally substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 5 -heterocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -alkyl-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 6 -,C 10 -C 14 -aryl, C 1 -C 5 -heteroaryl, C 6 -,C 10 -,C 14 -aryl-(C 1 -C 3 )-alkyl, C 1 -C 5 -heteroaryl-(C 1 -C 3 )-alkyl, N—C 1 -C 4 -alkylamino, N—C 1 -C 4 -alkylcarbonylamino, or N,N-di-C 1 -C 4 -alkylamino; or
is an optionally poly-V-substituted unsaturated 6-membered carbocycle; or
is an optionally poly-V-substituted unsaturated 4-, 5- or 6-membered heterocyclic ring, where

V is independently halogen, cyano, nitro, in each case optionally substituted C 1 -C 6 -alkyl, C 1 -C 4 -alkenyl, C 1 -C 4 -alkynyl, 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 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, or N,N-di-(C 1 -C 6 -alkyl)amino;
and/or one or more salts, N-oxides and/or tautomeric forms of the compounds of the formula (Ia″).

2. A compound according to claim 1 , wherein the compound of formula (Ia″) is a compound of formula (I-T3)

wherein,
not more than one moiety selected from A 1 , A 2 , A 3 , A 4 is N.

3. A compound according to claim 1 , wherein the compound of formula (Ia″) is a compound of formula (I-T2)

where not more than one moiety selected from A 1 , A 2 , A 3 , A 4 is N.

4. A compound according to claim 1 , wherein the compound of formula (Ia″) is a compound of formula (I-T4)

where not more than one moiety selected from A 1 , A 2 , A 3 , A 4 is N.

5. A compound according to claim 1 , wherein the compound of the formula (Ia″) is a compound of formula (I-T22)

where not more than one moiety selected from A 1 , A 2 , A 3 , A 4 is N.

6. A compound according to claim 1 , wherein the compound of formula (Ia″) is a compound of formula (I-T23)

where not more than one moiety selected from A 1 , A 2 , A 3 , A 4 is N.

7. A compound according to claim 1 , wherein the compound of formula (Ia″) is a compound of formula (I-T46)

where not more than one moiety selected from A 1 , A 2 , A 3 , A 4 is N.

8. A compound according to claim 1 , wherein W is O.

9. A compound according to claim 1 , wherein W is O and, R 8 is fluorine-substituted C 1 -C 3 -alkyl or -substituted C 1 -C 3 -alkoxy.

10. A compound according to claim 1 , wherein the A 1 to A 4 and B 1 to B 5 moieties are as follows:
A 1 is C—H,
A 2 is CR 3 or N,
A 3 is CR 4 ,
A 4 is C—H,
B 1 is CR 6 or N,
B 2 is C—H,
B 4 is C—H and
B 5 is CR 10 or N.

11. A compound according to claim 1 , wherein R 1 is H.

12. A compound according to claim 1 , wherein Q is C 1 -C 3 -alkyl, cyclopropyl, 1-(cyano)cyclopropyl, 1-(perfluorinated C 1 -C 3 -alkyl)cyclopropyl, 1-(C 1 -C 4 -alkyl)cyclopropyl, 1-(thiocarbamoyl)cyclopropyl, halogen-substituted C 1 -C 3 -alkyl, thietan-3-yl, N-methylpyrazol-3-yl or 2-oxo-2(2,2,2-trifluoroethylamino)ethyl.

13. An insecticidal composition, comprising a content of at least one compound according to claim 1 and an extender and/or a surface-active substance.

14. A method of controlling insects, arachnids and/or nematodes comprising allowing a compound according to claim 1 to act on the insects, arachnids and/or nematodes, and/or their habitat.

15. A method of controlling animal pests, comprising allowing a compound according to claim 1 to act on the pests and/or their habitat.

16. A method of controlling insects, arachnids and/or nematodes comprising allowing a composition according to claim 13 to act on the insects, arachnids or nematodes, and/or their habitat.

17. A method of controlling animal pests, comprising allowing a composition according to claim 13 to act on the pests and/or their habitat.

Assignees

• Bayer Cropscience Ag

Inventors

• Hallenbach Werner
• Schwarz Hans-Georg
• Ilg Kerstin
• Goergens Ulrich
• Koebberling Johannes
• Turgerg Andreas
• Boehnke Niels
• Maue Michael
• Velten Robert
• Harschneck Tobias
• Hahn Julia Johanna
• Horstmann Sebastian

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A61P33/02

  Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A01N43/72

  having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms · CPC title

• C07D207/337

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title