Novel phenylpyrazole insecticide compounds and compositions

Abstract

The present disclosure relates to new and improved insecticidal compounds of the phenylpyrazole class, according to the Formula I: wherein X, Y, Z, and Ar are as defined herein. In particular, the disclosure provides new insecticidal compounds for use against a variety of insects (arthropods), such as, for the treatment or prevention of disease or infestation on poultry and other livestock, horses, cats, dogs, and other companion animals, fields, crops, and other insecticidal uses. In particular embodiments, the present disclosure provides the use of said compounds for the treatment, control, suppression, or eradication, of an infection or infestation of an insect (arthropod), such as an adult insect, insect egg, insect larva, insect nymph, and / or insect pupa, including, but not limited to, the poultry mite, Dermanyssus gallinae.

Description

This disclosure relates to novel and improved phenylpyrazole insecticidal compounds according to Formula I, wherein X, Y, Z, and Ar are as defined herein. In particular, this disclosure provides novel insecticidal compounds for the control of a variety of insects (arthropods), such as for the treatment or prevention of diseases or infestations in poultry and other livestock, horses, cats, dogs and other companion animals, fields, crops, and other insecticidal uses. In certain embodiments, this disclosure provides the use of said compounds for the treatment, control, inhibition, or eradication of infections or infestations of insects (arthropods), such as adults, eggs, larvae, nymphs, and / or pupae, including but not limited to avian mites, such as the chicken mites (Dermanyssus gallinae). Abstract

Claims

MLC23P01PC1 CLAIMS What is claimed is:

1. A compound having the following general structure:, wherein: X is -N- or -CR1-; Y is -N- or -CR2-; Z is -CR3-; R1, R2, and R3are each independently selected from H, halo, cyano, nitro, hydroxy, amino, C1-6alkyl, C3-6cycloalkyl, C1-6haloalkyl, C1-6alkoxy, C1-6haloalkoxy, C3- 6cycloalkoxy, C3-6halocycloalkyl, NH(C1-6alkyl), N(C1-6alkyl)(C1-6alkyl), and 3-6 membered heterocycloalkyl, each of which is optionally substituted; Ar is phenyl or 5- or 6-membered heteroaryl, optionally substituted by 1-5 groups R; and each R is independently selected from halo, cyano, nitro, hydroxy, amino, C1-6alkyl, C3-6cycloalkyl, C1-6haloalkyl, C1-6alkoxy, C1-6haloalkoxy, C3-6halocycloalkyl, NH(C1-6alkyl), N(C1-6alkyl)(C1-6alkyl), and 3-6 membered heterocycloalkyl, each of which is optionally substituted; in free or salt form.

2. The compound according to claim 1, wherein X is -CR1- and Y is -CR2-.

3. The compound according to claim 1, wherein the compound is of the following general structure,MLC23P01PC1, wherein R1, R2, and R, are as defined in claim 1.

4. The compound according to any one of claims 1-3, wherein R1is selected from halo (e.g., F, Cl), cyano, C1-3alkyl (e.g., methyl, ethyl), and C1-3haloalkyl (e.g., trifluoromethyl), each of which is optionally substituted.

5. The compound according to any one of claims 1-4, wherein R2 is selected from H, halo (e.g., F, Cl), and cyano.

6. The compound according to any one of claims 1-5, wherein R3 selected from hydroxy, amino, and NH(C1-6alkyl) (e.g., N-methylamino), each of which is optionally substituted.

7. The compound according to any one of claims 1-6, wherein Ar is phenyl or 5- or 6- membered heteroaryl, optionally substituted by 1-5 groups R.

8. The compound according to claim 1, wherein the compound is of the following general structure,, wherein R is as defined in claim 1.MLC23P01PC1 9. The compound according to any one of claims 1-8, wherein each R is independently selected from halo (e.g., F, Cl, Br, I), cyano, nitro, hydroxy, C1-6haloalkyl (e.g., trifluoromethyl), C1- 6haloalkoxy (e.g., trifluoromethoxy), and C3-6halocycloalkyl (e.g., 2,2-difluorocyclopropyl), each of which is optionally substituted.

10. A compound according to any one of claims 1-8, wherein Ar is selected from 2,6-dichloro-4- trifluoromethyl, 2,6-dichloro-4-trifluoromethoxy, 2,6-dichloro-4-bromo, 2,6-dichloro-4- difluoromethyl, 2,6-dichloro-4-difluoromethoxy, 2,6-dichloro-4-fluoromethyl, 2,6-dichloro- 4-fluoromethoxy, 2,6-dichloro-4-methyl, 2,6-dichloro-4-methoxy, 2,4,6-trichloro, 2-chloro- 4-trifluoromethoxy, 2-chloro-4-bromo, 2-chloro-4-difluoromethyl, 2-chloro-4- difluoromethoxy, 2-chloro-4-fluoromethyl, 2-chloro-4-fluoromethoxy, 2-chloro-4-methyl, 2- chloro-4-methoxy, 2,4-dichloro, and 2-chloro-4-bromo.

11. A compound of the Formula I, wherein the Compound of Formula I is:, in free or salt form.

12. A compound according to claim 1, wherein the Compound of Formula I is:free or salt form, wherein R1 is as defined in claim 1.MLC23P01PC1 13. The compound according to claim 12, wherein R1is selected from halo (e.g., F, Cl), cyano, C1-3alkyl (e.g., methyl, ethyl), C3-6cycloalkyl (e.g., cyclopropyl), and C1-3haloalkyl (e.g., trifluoromethyl).

14. The compound according to claim 12, wherein the compound is selected from the group consisting of: , , ,MLC23P01PC1each in free or salt form.

15. A pharmaceutical or insecticidal composition comprising an effective amount of a compound according to any one of claims 1-14, in free or salt form, in admixture with a pharmaceutically acceptable or insecticidally acceptable diluent or carrier.

16. A pharmaceutical or insecticidal composition comprising an effective amount of a compound according to claim 14, in free or salt form, in admixture with a pharmaceutically acceptable or insecticidally acceptable diluent or carrier, wherein the composition is formulated for delivery by spray (e.g., liquid or aerosol spray).

17. The composition according to claim 16, wherein the composition is a solution comprising the compound of Formula I, dissolved in a 2-butoxyethanol, ethanol, and water in a 7:2:1 v / v ratio.

18. The compound according to any one of claims 1-14, or a composition according to any one of claims 1-14, for use to treat, control, suppress, or eradicate, an infection or infestation of an insect (arthropod), such as an adult insect, insect egg, insect larva, insect nymph, and / or insect pupa, optionally wherein the insect is the poultry mite or red mite, Dermanyssus gallinae, and further optionally wherein the compound or composition is administered to chickens or applied to chicken coops, chicken pens, chicken cages, other chicken enclosures, chicken farms, or chicken feed.MLC23P01PC1 19. The compound according to any one of claims 1-14, or a composition according to any one of claims 1-14, for use to treat, control, suppress, or eradicate, an infection or infestation of an insect (arthropod), such as an adult insect, insect egg, insect larva, insect nymph, and / or insect pupa, wherein the insect is selected from one or more of fleas, ticks, mites, lice, fire ants, termites, beetles, cockroaches, mole crickets, thrips, rootworms, and weevils