Compounds for controlling arthropods

Patent metadata

Field	Value
Publication number	US-10150737-B2
Application number	US-201415033464-A
Country	US
Kind code	B2
Filing date	Nov 5, 2014
Priority date	Nov 5, 2013
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

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″)

where
D 1 is C—R 11 ;
D 2 is C—R 11 or N;
D 3 is N;
D 4 is C;
D 5 is C—R 11 ;
◯ is an aromatic system; and
R 1 is optionally substituted C 1 -C 6 -alkyl;
the following moieties are as follows:
A 1 is C—H,
A 2 is CH or N,
A 3 is CR 4 ,
A 4 is C—H,
B 1 is CR 6 ,
B 2 is C—H,
B 4 is C—H and
B 5 is CR 10 or N;
R 4 , R 6 , and R 10 are each independently H, halogen, cyano, nitro, or 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;
R 8 is fluorine-substituted C 1 -C 4 -alkoxy or fluorine-substituted C 1 -C 4 -alkyl;
R 11 is H;
W is O;
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 2 -C 4 -alkenyl, C 2 -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 tautomeric forms of a compound of formula (Ia″).

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

3. A compound according to claim 1 , wherein R 1 is methyl.

4. 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.

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

6. A method for controlling plant pests, comprising applying a compound according to claim 1 to control the plant pests.

7. Seed treated with a compound according to claim 1 .

8. The compound according to claim 1 , wherein
R 4 , R 6 , and R 10 are each independently hydrogen, halogen, cyano, or in each case optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 6 -alkoxy.

9. The compound according to claim 4 , wherein
R 4 , R 6 , and R 10 are each independently hydrogen, halogen, cyano, or in each case optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 6 -alkoxy.

10. The compound according to claim 1 , wherein
R 1 is methyl or ethyl;
R 4 is Cl, methyl, cyclopropyl or OCH 3 ;
R 6 is Cl, methyl, CF 3 , cyano, OCF 3 , OC 2 H 5 or OCHF 2 ;
R 10 is Cl, methyl, hydrogen, OC 2 H 5 or I; and
Q is cyclopropyl or 1-(cyano)cyclopropyl.

11. The method according to claim 6 , wherein the pests are insects, arachnids or nematodes.

12. The method according to claim 6 , wherein the pests are Rhipicephalus sanguineus, Ctenocephalides felis, Amblyomma hebraeum, Boophilus microplus, Lucilia cuprina, Musca domestica, Meloidogyne incognita, Myzus persicae, Phaedon cochleariae, Spodoptera frugiperda, Tetranychus urticae, Anopheles gambiae strain RSPH (homozygote kdr), Anopheles funestus strain FUMOZ-R or Aedes aegypti strain MONHEIM.

13. The compound according to claim 1 , wherein Q is cyclopropyl or 1-(cyano)cyclopropyl.

14. The compound according to claim 13 , wherein
R 4 , R 6 , and R 10 are each independently hydrogen, halogen, cyano, or in each case optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 6 -alkoxy.

Assignees

• Bayer Cropscience Ag

Inventors

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

Classifications

• A61P33/02

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

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/10

  Anthelmintics · CPC title

• A01N43/72

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

• C07D231/12 Primary

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