Aminobenzamide derivatives as useful agents for controlling animal parasites

Abstract

The invention relates to a composition comprising at least one aminobenzamide compound or a salt thereof for controlling animal parasites, veterinary pharmaceutical compositions comprising at least one aminobenzamide of formula (I) for preventing infection with diseases transmitted through parasites, its use for the preparation of a veterinary pharmaceutical for controlling animal parasites, and a method for preventing infection with diseases transmitted through parasites.

Claims

1. A method for preventing an infection with diseases transmitted through acari selected from the group consisting of Amblyomma americanum, Dermacentor variabilis, Dermacentor reticulatus, and Rhipicephalus sanguineus, comprising administering orally, topically, or parenterally to a domestic animal, companion animal, or agricultural livestock in need of said preventing a compound having a formula (I-1) ##STR00007## wherein X represents a hydrogen atom or a halogen atom; R.sup.1 represents a hydrogen atom or a C.sub.1-C.sub.6 alkyl group; R.sup.3 and R.sup.5 represents, independent from each other, a halogen atom, a C.sub.1-C.sub.4 alkyl group, or a C.sub.1-C.sub.4 haloalkyl group, R.sup.4 represents a C.sub.1-C.sub.4 haloalkyl group; L represents a phenyl group or a 2-halopyridin-3-yl group; or salts thereof.

2. The method of claim 1, wherein said acari is selected from the group consisting of Amblyomma americanum, Dermacentor variabilis, and Dermacentor reticulatus.

3. The method of claim 1, wherein said acari is Dermacentor variabilis.

Description

EXAMPLE NO. 1

Boophilus microplusTest (Injection)

(1) Solvent: dimethyl sulfoxide

(2) To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with water to the desired concentration.

(3) Five adult engorged female ticks (Boophilus microplus) are injected with compound solution into the abdomen. Ticks are transferred into replica plates and incubated in a climate chamber for a period of time. Egg deposition of fertile eggs is monitored.

(4) After the specified period of time, mortality in % is determined. 100% means that all eggs are infertile; 0% means that all eggs are fertile.

(5) In this test for example, the following compounds from the preparation examples showed good activity of 80% at application rate of 20 g/animal:

(6) Example number I-1-5, I-1-6, I-1-7, I-1-15, I-1-20, I-1-24, I-1-29, I-1-30, I-1-32, I-1-35, I-1-36, I-1-39, I-1-40, I-1-41, I-1-42, I-1-43, I-1-44, I-1-45, I-1-46, I-1-49, I-1-51, I-1-52, I-1-54, I-1-55, I-1-56, I-1-57, I-1-58, I-1-59, I-1-60, I-1-61, I-1-62, I-1-63, I-1-64, I-1-66, I-1-72, I-1-75, I-1-77, I-1-88, I-1-134, I-1-139, I-1-149, I-1-150, I-1-151, I-1-154, I-1-155, I-1-156, I-1-157, I-1-158, I-1-159, I-1-160, I-1-161, I-1-162, I-1-163, I-1-164, I-1-165, I-1-166, I-1-167, I-1-168, I-1-169, I-1-170, I-1-171, I-1-173, I-1-174, I-1-175, I-1-176, I-1-177, I-1-178, I-1-179, I-1-180, I-1-181, I- 1-182, I-1-183, I-1-184, I-1-185, I-1-186, I-1-187, I-1-188, I-1-189, I-1-190, I-1-191, I-1-192, I-1-193, I-1-194, I-1-195, I-1-196, I-1-197, I-1-198, I-1-199, I-1-200, I-1-201, I-1-202, I-1- 203, I-1-204, I-1-205, I-1-206, I-1-207, I-1-208, I-1-209, I-1-210, I-1-211, I-1-212, I-1-213, I- 1-214, I-1-215, I-1-216, I-1-217, I-1-218, I-1-219, I-1-221, I-1-222, I-1-223, I-1-224, I-1-225, I-1-226, I-1-227, I-1-228, I-1-229, I-1-230, I-1-231, I-1-233, I-1-234, I-1-235, I-1-236, I-1-237, I- 1-238, I-1-239, I-1-240, I-1-241, I-1-242, I-1-243, I-1-244, I-1-245, I-1-246, I-1-247, I-1-248, I-1- 249, I-1-250, I-1-251, I-1-252, I-1-253, I-1-254, I-1-255, I-1-256, I-1-257, I-1-258 I-1-259, I-1-260, I-1-261, I-1-262, I-1-263, I-1-264, I-1-265, I-1-266, I-1-267, I-1-268, I-1-269, I-1-270, I-1-271, I-1- 272, I-1-273, I-1-274, I-1-275, I-1-276, I-1-277, I-1-278, I-1-279, I-1-280, I-1-281, I-1-282, I-1-283, I- 1-284, I-1-285, I-1-286, I-1-287, I-1-288, I-1-289, I-1-290, I-1-291, I-1-292, I-1-293, I-1-294, I-1- 295, I-1-296, I-1-297, I-1-298, I-1-299, I-1-300, I-1-301, I-1-302, I-1-303, I-1-304, I-1-305, I-1-306, I-1-307, I-1-308, I-1-309, I-1-310, I-1-311, I-1-312, I-1-313, I-1-314, I-2-1, I-2-2, I-2-3, I-2-4, I-2-5, I-2-6, I-2-7, I-2-8, I-2-17, I-2-18

EXAMPLE NO. 2

Ctenocephalides felisTest (CTECFE)

(7) Solvent: dimethyl sulfoxide

(8) To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with cattle blood to the desired concentration.

(9) Approximately 10 to 15 adult unfed (Ctenocepahlides felis) are placed in flea chambers. The blood chamber, sealed with parafilm on the bottom are filled with cattle blood supplied with compound solution and placed on top of the flea chamber, so that the fleas are able to suck the blood. The blood chamber is heated to 37 C. whereas the flea chamber is kept at room temperature.

(10) After the specified period of time, mortality in % is determined. 100% means that all the fleas have been killed; 0% means that none of the fleas have been killed.

(11) In this test for example, the following compounds from the preparation examples showed good activity of 80% at application rate of 100 ppm:

(12) Example number I-1-5, I-1-6, I-1-7, I-1-30, I-1-32, I-1-35, I-1-36, I-1-40, I-1-42, I-1-46, I-1-49, I-1-51, I-1-52, I-1-54, I-1-55, I-1-56, I-1-57, I-1-59, I-1-61, I-1-62, I-1-63, I-1-66, I-1-72, I-1-75, I-1-88, I-1-134, I-1-139, I-1-149, I-1-150, I-1-151, I-1-155, I-1-156, I-1-159, I-1-162, I-1-164, I-1-165, I-1-166, I-1-167, I-1-168, I-1-169, I-1-170, I-1-171, I-1-173, I-1-174, I-1-175, I-1-176, I- 1-177, I-1-178, I-1-180, I-1-181, I-1-182, I-1-183, I-1-184, I-1-185, I-1-186, I-1-187, I-1-188, I-1- 189, I-1-191, I-1-192, I-1-193, I-1-194, I-1-195, I-1-196, I-1-197, I-1-198, I-1-199, I-1-200, I- 1-201, I-1-203, I-1-204, I-1-206, I-1-207, I-1-208, I-1-209, I-1-210, I-1-211, I-1-212, I-1-213, I-1-214, I-1-217, I-1-218, I-1-219, I-1-220, I-1-221, I-1-222, I-1-223, I-1-224, I-1-226, I-1- 227, I-1-229, I-1-230, I-1-231, I-1-233, I-1-234, I-1-235, I-1-238, I-1-241, I-1-242, I-1-243, I-1-244, I- 1-245, I-1-246, I-1-247, I-1-248, I-1-249, I-1-250, I-1-251, I-1-252, I-1-253, I-1-254, I-1-255, I-1- 256, I-1-257, I-1-258 I-1-259, I-1-260, I-1-261, I-1-262, I-1-263, I-1-264, I-1-265, I-1-266, I-1-267, I-1-269, I-1-271, I-1-274, I-1-275, I-1-276, I-1-277, I-1-278, I-1-279, I-1-280, I-1-281, I-1-282, I-1- 283, I-1-284, I-1-287, I-1-288, I-1-289, I-1-292, I-1-293, I-1-295, I-1-296, I-1-297, I-1-298, I-1-299, I- 1-300, I-1-301, I-1-302, I-1-304, I-1-306, I-1-307, I-1-308, I-1-309, I-1-310, I-1-311, I-1-312, I- 1-313, I-1-314, I-2-1, I-2-2, I-2-4, I-2-5, I-2-6, I-2-7, I-2-8

EXAMPLE NO. 3

Lucillia cuprinaTest

(13) Solvent: dimethyl sulfoxide

(14) To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with water to the desired concentration.

(15) Approximately 20-30 (Lucilia cuprina larvae) are transferred into a test tube containing ice of minced horse meat and 0.5 ml aqueous dilution of test compound.

(16) After the specified period of time, mortality in % is determined. 100% means that all the larvae have been killed; 0% means that none of the larvae have been killed.

(17) In this test for example, the following compounds from the preparation examples showed good activity of 80% at application rate of 100 ppm:

(18) Example number I-1-5, I-1-6, I-1-7, I-1-15, I-1-24, I-1-29, I-1-30, I-1-32, I-1-35, I-1-36, I-1-39, I-1-40, I-1-41, I-1-42, I-1-43, I-1-44, I-1-45, I-1-46, I-1-49, I-1-51, I-1-52, I-1-54, I-1-55, I-1-56, I-1-57, I-1-58, I-1-59, I-1-60, I-1-61, I-1-62, I-1-63, I-1-64, I-1-66, I-1-72, I-1-75, I-1-77, I-1-88, I-1-134, I-1-139, I-1-149, I-1-150, I-1-151, I-1-154, I-1-155, I-1-156, I-1-159, I-1-160, I-1-164, I-1-165, I-1-166, I-1-167, I-1-168, I-1-170, I-1-171, I-1-173, I-1-174, I-1-175, I-1-176, I-1-177, I- 1-178, I-1-179, I-1-180, I-1-181, I-1-182, I-1-183, I-1-184, I-1-185, I-1-186, I-1-187, I-1-188, I-1- 189, I-1-190, I-1-191, I-1-192, I-1-193, I-1-194, I-1-195, I-1-196, I-1-197, I-1-198, I-1-199, I-1-200, I-1-204, I-1-206, I-1-207, I-1-208, I-1-209, I-1-210, I-1-211, I-1-213, I-1-214, I-1- 215, I-1-216, I-1-218, I-1-219, I-1-220, I-1-221, I-1-222, I-1-223, I-1-224, I-1-225, I-1-226, I-1- 227, I-1-229, I-1-230, I-1-231, I-1-232, I-1-233, I-1-234, I-1-235, I-1-237, I-1-238, I-1-239, I-1-240, I- 1-241, I-1-242, I-1-243, I-1-244, I-1-245, I-1-246, I-1-247, I-1-248, I-1-249, I-1-250, I-1-251, I- 1-252, I-1-255, I-1-256, I-1-257, I-1-258 I-1-259, I-1-260, I-1-261, I-1-262, I-1-263, I-1-264, I-1-265, I-1-266, I-1-267, I-1-268, I-1-269, I-1-270, I-1-271, I-1-272, I-1-273, I-1-274, I-1-275, I-1-276, I- 1-277, I-1-278, I-1-279, I-1-280, I-1-281, I-1-282, I-1-283, I-1-284, I-1-285, I-1-286, I-1-287, I-1- 288, I-1-289, I-1-291, I-1-292, I-1-293, I-1-294, I-1-295, I-1-296, I-1-297, I-1-298, I-1-299, I-1-300, I- 1-301, I-1-302, I-1-303, I-1-304, I-1-306, I-1-308, I-1-309, I-1-310, I-1-311, I-1-312, I-1-313, I-1- 314, I-2-1, I-2-2, I-2-3, I-2-4, I-2-5, I-2-6, I-2-7, I-2-8

EXAMPLE No. 4

Musca domesticaTest

(19) Solvent: dimethyl sulfoxide

(20) To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with water to the desired concentration.

(21) Prior to the assay, a piece or kitchen sponge is soaked with a mixture of sugar and compound solution and placed into a container. 10 adults (Musca domestica) are placed into the container and closed with a perforated lid.

(22) After the specified period of time, mortality in % is determined. 100% means that all the flies have been killed; 0% means that none of the flies have been killed.

(23) In this test for example, the following compounds from the preparation examples showed good activity of 80% at application rate of 100 ppm:

(24) Example number I-1-5, I-1-6, I-1-7, I-1-32, I-1-44, I-1-52, I-1-54, I-1-62, I-1-63, I-1-72, I-1-75, I-1-139, I-1-173, I-1-174, I-1-175, I-1-176, I-1-177, I-1-178, I-1-185, I-1-191, I-1-193, I-1- 194, I-1-195, I-1-196, I-1-197, I-1-199, I-1-208, I-1-209, I-1-210, I-1-222, I-1-229, I-1-238, I-1-243, I-1-244, I-1-245, I-1-246, I-1-247, I-1-255, I-1-258, I-1-260, I-1-261, I-1-262, I-1-263, I-1-264, I-1-265, I-1-266, I-1-267, I-1-269, I-1-271, I-1-274, I-1-275, I-1-277, I-1-278, I-1-279, I-1-280, I- 1-281, I-1-282, I-1-283, I-1-284, I-1-285, I-1-288, I-1-289, I-1-292, I-1-300, I-1-302, I-1-306, I-1- 308, I-1-309, I-1-310, I-1-311, I-1-312, I-1-313, I-1-314, I-2-1, I-2-2, I-2-3, I-2-4, I-2-6, I-2-7

EXAMPLE NO. 5

Boophilus microplus (Dip)

(25) Solvent: dimethyl sulfoxide

(26) To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with water to the desired concentration.

(27) Eight to ten adult engorged female Boophilus microplus ticks are placed in perforated plastic beakers and immersed in aqueous compound solution for one minute. Ticks are transferred to a filter paper in a plastic tray and incubated in a climate chamber for a period of time. Egg deposition of fertile eggs is monitored.

(28) After the specified period of time, mortality in % is determined. 100% means that all eggs are infertile; 0% means that all eggs are fertile.

(29) In this test for example, the following compounds from the preparation examples showed good activity of 80% at application rate of 100 ppm:

(30) Example No. I-1-5, I-1-6, I-a-54, I-1-192, I-1-194, I-1-195, I-1-238, I-1-245, I-1-246, I-1-260, I-1-274, I-1-275, I-1-278, I-1-280, I-1-281, I-1-282, I-1-283

EXAMPLE NO. 6

Amblyomma hebraeumTest (AMBYHE)

(31) Solvent: dimethylsulfoxide

(32) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with containing solvent to the desired concentration.

(33) Nymphs of the tick Amblyomma hebraeum are placed in perforated plastic beakers and immersed in aqueous compound solution for one minute. Ticks are transferred to a filter paper in a Petri dish and incubated in a climate chamber for 42 days.

(34) After the specified period of time, mortality in % is determined. 100% means that all the ticks have been killed; 0% means that none of the ticks have been killed.

(35) In this test for example, the following compounds from the preparation examples showed good activity of 80% at application rate of 100 ppm:

(36) Example No. I-1-5, I-1-280, I-1-281, I-1-282

(37) When not mentioned otherwise the tested compounds or compositions were administered in a suitable formulation.