Cyclopropylamide compounds against fish parasites

Abstract

The present invention relates to cyclopropylamide compounds useful for the treatment of parasitic infestations in fish. The compounds have the formula (I): [Formula 1] TIFF2024526499000065.tif69170

Description

Technical Field

[0001] The present invention relates to the treatment or prevention of parasitic infections in animals.

Background Art

[0002] [[ID=[]] Parasitism of fish by parasites is a major problem for commercial fish farming. Aquaculture farmers facing parasite problems usually suffer significant financial losses and bear additional costs.

[0003] The sea lamprey is an external parasite belonging to the subclass of lampreys that affects fish, especially farmed salmonids, by feeding on the mucus, skin, tissues and blood of the fish host. The sea lamprey can cause serious harm to the host fish (i.e., severe fin damage, skin erosion, bleeding, and open wounds). Furthermore, the sea lamprey can cause a chronic stress response in fish, which may make the fish more susceptible to other diseases. Furthermore, the sea lamprey is thought to have an immunomodulatory effect on the host fish and may function as a vector in the transmission of other fish diseases. Damage caused by parasitic infection from the sea lamprey results in significant animal welfare problems, fish losses and increased costs. Parasitism by the sea lamprey is considered one of the most important disease problems in the farming of salmonids, especially the Atlantic salmon (Salmo salar) and rainbow trout (Oncorhynchus mykiss).

[0004] In other fish species, such as sea bream, tilapia, koi, etc., the sea lamprey may also parasitize. In addition to the costs associated with treatment, a decrease in the classification evaluation of slaughtered fish and a decrease in the growth rate due to a decrease in feed intake contribute to economic losses.

[0005] On the other hand, sea lice are widespread and encountered in all fish farms. Severe infestations can kill fish. Norwegian fish farms have reported mortality rates exceeding 50% based on sea louse infestations. The extent of the damage depends on the time of year and environmental factors, such as water salinity and average water temperature. In the first stage, sea louse infestations are seen as the appearance of parasites attached to the fish, and then more clearly as damage caused to the skin and tissues. The most severe damage is observed in smolts in the phase of transition from freshwater to seawater. The situation is further exacerbated by specific conditions in the farm: salmon of different age groups but the same weight class are kept together; contaminated nets or cages are used; high salinity should be found; flow through nets and cages is minimal; and the fish are kept in very confined spaces.

[0006] Several treatments for controlling sea lice are already on the market, including bath treatments with organophosphates (e.g., dichlorvos and azamethiphos) and pyrethroids (e.g., cypermethrin and deltamethrin), as well as feed treatments with avermectin (e.g., ivermectin and emamectin benzoate) and growth regulators (e.g., lufenuron and teflubenzuron). However, resistance to many of these treatments has been observed, and therefore, new treatments, especially those with long-lasting effects, are still needed.

[0007] Therefore, there is still a need for new treatment options for controlling fish lice infestations, particularly in farmed fish populations, that are safe and selective against target parasites and can treat lice populations that exhibit reduced resistance or susceptibility to current products. The present invention provides a new treatment option for controlling fish lice.

[0008] International Publication Nos. 2016 / 168056, 2016 / 168058, 2016 / 168059, and 2018 / 071327 disclose certain compounds that possess insecticidal and acaricidal activity and are therefore useful for controlling agricultural plant pests. However, none of these citations exemplify or describe their use in aquaculture.

[0009] Surprisingly, the aliphatic cyclopropylamide compound of formula (I) was found to be effective in controlling parasitic infestations of fish, particularly those of sea lice. [Overview of the project]

[0010] In a first aspect, the present invention is for use in a method for controlling parasitic infections of fish.

[0011] [ka]

[0012] With respect to compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers, in the formula, R 1 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 2 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 3 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 4is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2 and S-(halo)5; R 5 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2 and (C1-C6)haloalkyl-S(O)2NH2; R 6 is selected from the group consisting of H and (C1-C6)alkyl; R 7 is selected from the group consisting of H, F, Cl, Br and I; R 8 is selected from the group consisting of F, Cl, Br and I; R 9 is selected from the group consisting of H and (C1-C6)alkyl; R 10This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 11 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 12 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 13H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and triazolyl; R 14 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 15 This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 16(C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkylphenyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, O-phenyl, O-(C2~C8)alkenyl, O-(C1~C8)alkyl(C3~C8)cycloalkyl, O- Selected from the group consisting of (C1~C8)alkylphenyl, (C1~C8)alkyl-O-(C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl~C(=O)NH-(C1~C8)haloalkyl, (C1~C8)alkyl-NHC(O)-(C1~C8)alkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, and (C1~C8)alkyl-S(O)2-NH2, Here, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, haloalkyl, and phenyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, N((C1~C8)alkyl)2, C(O)O(C1~C8)alkyl, benzothioenyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl; R 15 and R 16 Together, they can optionally form a 2- to 5-membered saturated or unsaturated hydrocarbyl bond which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen. Here, the hydrocarbyl bond may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NH2, and NO2; or R 16 The group is selected from (C3~C8) cycloalkyl, azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinol. Here, each cycloalkyl, azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide The oxide and thioxothiazolidinol may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0013] Suitable compounds for use according to the present invention and its embodiments are R 16 is selected from the group consisting of (C1-C8) alkyl, (C3-C8) cycloalkyl, (C1-C8) alkyl-O-(C1-C8) alkyl, (C1-C8) alkyl(C3-C8) cycloalkyl, (C1-C8) alkylphenyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) haloalkyl, (C1-C8) alkyl-S-(C1-C8) alkyl, (C1-C8) alkyl-S(O)-(C1-C8) alkyl, (C1-C8) alkyl-S(O)2-(C1-C8) alkyl, O-phenyl, O-(C2-C8) alkenyl, O-(C1-C8) alkyl(C3-C8) cycloalkyl, O-(C1-C8) alkylphenyl, (C1-C8) alkyl-O-(C1-C8) alkyl(C3-C8) cycloalkyl, (C1-C8) alkyl-O-(C1-C8) haloalkyl, (C1-C8) alkyl~C(=O)NH-(C1-C8) haloalkyl, (C1-C8) alkyl-NHC(O)-(C1-C8) alkyl, (C1-C8) alkyl-S-(C1-C8) haloalkyl, (C1-C8) alkyl-S(O)-(C1-C8) haloalkyl, (C1-C8) alkyl-S(O)2-(C1-C8) haloalkyl, (C1-C8) alkyl-S(O)2-NH2, and heterocycles; where each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, haloalkyl and phenyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1-C8) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) alkoxy, (C1-C8) haloalkyl, N((C1-C8) alkyl)2, C(O)O(C1-C8) alkyl, benzothienyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl and triazolyl; The heterocycle is selected from the group consisting of azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinol, and Each (C3-C8) cycloalkyl and heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl.

[0014] Compounds suitable for use according to the present invention and its embodiments are R 16(C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8) Selected from the group consisting of alkyl-S(O)2-(C1~C8)alkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, and (C1~C8)alkyl-S(O)2-NH2, and heterocyclic rings, Here, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl compound may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, (C1-C8)haloalkyl, C(O)O(C1-C8)alkyl, oxoimidazolidinyl, furanyl, and pyrazolyl.

[0015] Compounds suitable for use according to the present invention and its embodiments are R 16 The heterocycle is a compound selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide.

[0016] Compounds suitable for use according to the present invention and its embodiments are R 16Each (C3-C8) cycloalkyl or heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl(C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl.

[0017] Compounds suitable for use according to the present invention and its embodiments are: R 1 However, it is selected from the group consisting of H, F, and Cl; R 2 However, it is selected from the group consisting of H, F, Cl, Br, CH3, and CF3; R 3 However, it is selected from the group consisting of H, F, Cl, CH3, and CHF2, CF3, OCF3; R 4 However, it is selected from the group consisting of H, F, Cl, Br, CH3, and CF3; R 5 However, H is; R 6 However, H is; R 7 However, it is selected from the group consisting of Cl and Br; R 8 However, it is selected from the group consisting of Cl and Br; R 9 , R 10 , and R 11 However, H is; R 12 However, it is selected from the group consisting of H, F, Cl, Br, and CH3; R 13 However, it is selected from the group consisting of H, F, Cl, CH3, and CF3; R 14 However, it is either H or F; R 15However, it is selected from the group consisting of H and CH3; Q1 and Q2 are compounds in which O is present.

[0018] In the proper use of the present invention and / or any embodiment thereof, the parasitic organism is a sea louse.

[0019] In suitable use of the present invention and / or any embodiment thereof, the parasite is at least one of Lepeophtheirus salmonis, Caligus celmensi, Caligus curtus, Caligus dussumieri, Caligus elongates, Caligus longicaudatus, Caligus rogercresseyi, or Caligus stromii.

[0020] In appropriate use of the present invention and / or any embodiment thereof, the parasitic organisms are copepods, pre-adult or adult sea lice, or mixed parasites at various stages.

[0021] In a suitable use of the present invention and / or any embodiment thereof, the parasitism rate in fish is an average of 0.5 to 3 parasites per fish in a fish facility, and preferably the parasite is an adult female sea louse.

[0022] In appropriate use of the present invention and / or any embodiment thereof, the method includes administering a compound of formula (I) as defined in any one of claims 1 to 4 to a fish by oral administration, local administration such as by bath treatment, or by intraperitoneal or intramuscular injection.

[0023] In appropriate use of the present invention and / or any embodiment thereof, the method comprises administering a compound of formula (I) as defined in any one of claims 1 to 4 to a fish by oral administration, wherein the oral administration comprises administering a medicated fish feed containing a therapeutically effective amount of the compound and fish feed.

[0024] In a suitable use of the present invention and / or any embodiment thereof, the method comprises administering a compound of formula (I) as defined in any one of claims 1 to 4 by a bath treatment, the bath treatment comprising immersion of a fish in water containing a therapeutically effective amount of the compound.

[0025] In the proper use of the present invention and / or any embodiment thereof, fish is a salmonid animal.

[0026] The present invention also relates to a premix comprising a compound of formula (I) as defined in any embodiment described herein, further comprising nutrients.

[0027] Preferably, the premix contains nutrients in the form of pellets, and the pellets are coated with a composition comprising a compound of formula (I) as defined in any embodiment described herein.

[0028] In a suitable embodiment, a medicated fish feed is provided, comprising a premix and fish feed as defined herein.

[0029] In a preferred embodiment, the parasitic organism is a sea louse.

[0030] In one embodiment, the present invention provides a composition comprising one or more compounds of formula (I) according to any embodiment described herein and a veterinarily acceptable formulation adjuvant for use in controlling parasitic infections in fish populations.

[0031] Another embodiment is a premix comprising nutrients, formulation adjuvants, and at least one compound of formula (I) according to any embodiment described herein.

[0032] Another embodiment is a medicinal fish feed, or premix and nutritional fish feed, comprising such composition according to any embodiment described herein.

[0033] Further embodiments relate to kits containing such compounds or compositions according to any embodiment described herein, and instructions for administering the compositions to fish.

[0034] A preferred embodiment relates to a kit comprising a premix according to any embodiment described herein, instructions for preparing a medicated fish feed for use in controlling sea louse infestations, and / or instructions for administering the medicated fish feed to a fish population.

[0035] Another preferred embodiment relates to a kit comprising a stock solution according to any embodiment described herein, as well as instructions for preparing medicinal water for bath treatment, and / or instructions for immersing fish to control sea louse infestation. [Modes for carrying out the invention]

[0036] This detailed description of preferred embodiments is intended solely to inform those skilled in the art of the applicant's invention, its principles, and its practical applications, so that those skilled in the art may adapt and apply the invention in numerous forms, as these may best suit the requirements of a particular application. This detailed description and its specific examples illustrate preferred embodiments of the invention, but are for illustrative purposes only.

[0037] Therefore, the present invention is not limited to the preferred embodiments described herein and can be modified in various ways. Furthermore, for the purpose of brevity and readability, only some combinations of embodiments are explicitly described, but it should be understood that other combinations of embodiments are also contemplated.

[0038] The inventors of the present invention have discovered that parasitic organisms, particularly fish lice infestations, can be treated or prevented by administering an effective amount of an aliphatic cyclopropylamide compound of formula (I).

[0039] The advantage of such a method is that it is effective in both treating existing sea louse infestations and preventing new infestations, and therefore prevents the establishment of adult sea louse colonies, which is known to be the most harmful stage. The resistance-destruction properties of such compounds are very good.

[0040] Surprisingly, the aliphatic cyclopropylamide compound of formula (I) was found to be effective and, despite having low toxicity to fish, could be successfully used against juvenile and adult sea lice in fish.

[0041] A further advantageous property of the aliphatic cyclopropylamide compound of formula (I) is that, at the proposed concentrations, it does not harm other marine animals such as lobsters, oysters, crustaceans (excluding sea lice), fish, and marine plants.

[0042] As shown in the examples, administration of the aliphatic cyclopropylamide compound of formula (I) described in this application can effectively control sea louse infestations using oral administration, particularly when using a medicated feed administration containing the compound of the present invention and fish feed. Furthermore, it has been shown that the compound of formula (I) can be effectively used to control resistant populations of fish parasites.

[0043] Therefore, the present invention represents an advance in the control of fish parasites, particularly sea lice, enabling effective control of sea lice in fish populations.

[0044] The compound of formula (I) can be used to control parasitic infestations in fish. The uses of the present invention are described in more detail below.

[0045] The compound of formula (I) is hereinafter referred to as the aliphatic cyclopropylamide compound of formula (I) or the compound(s) according to the present invention.

[0046] Therefore, the present invention provides the following formula for use in a method for controlling parasitic infections of fish:

[0047] [ka]

[0048] With respect to compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers, in the formula, R 1 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 2H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 3 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 4H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 5 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 6 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 7 It is selected from the group consisting of H, F, Cl, Br, and I; R 8 It is selected from the group consisting of F, Cl, Br, and I; R 9 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 10This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 11 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 12 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 13H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and triazolyl; R 14 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 15 This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 16(C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkylphenyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, O-phenyl, O-(C2~C8)alkenyl, O-(C1~C8)alkyl(C3~C8)cycloalkyl, O- Selected from the group consisting of (C1~C8)alkylphenyl, (C1~C8)alkyl-O-(C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl~C(=O)NH-(C1~C8)haloalkyl, (C1~C8)alkyl-NHC(O)-(C1~C8)alkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, and (C1~C8)alkyl-S(O)2-NH2, Here, each alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, and phenyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, N((C1~C8)alkyl)2, C(O)O(C1~C8)alkyl, benzothioenyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl; R 15 and R 16 Together, they can optionally form a 2- to 5-membered saturated or unsaturated hydrocarbyl bond which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen. Here, the hydrocarbyl bond may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NH2, and NO2; or R 16 The group is selected from (C3~C8) cycloalkyl, azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinol. Here, each cycloalkyl, azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide and thioxothiazoli Dinonyl may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl; Q 1 and Q 2Each is independently selected from the group consisting of O and S.

[0049] In one embodiment and / or multiple embodiments thereof, R 1 The group is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy.

[0050] In one embodiment and / or multiple embodiments thereof, R 1 The group is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy.

[0051] In one embodiment and / or multiple embodiments thereof, R 1 The element is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy.

[0052] In one embodiment and / or multiple embodiments thereof, R 1 The group is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0053] In one embodiment and / or multiple embodiments thereof, R 1 The group is selected from the group consisting of H, F, Cl, Br, I, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0054] In one embodiment and / or multiple embodiments thereof, R 1 The group is selected from the group consisting of H, F, Cl, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0055] In one embodiment and / or multiple embodiments thereof, R 1 It is selected from the group consisting of H, F, and Cl.

[0056] In one embodiment and / or multiple embodiments thereof, R 1 It is selected from the group consisting of H and F.

[0057] In one embodiment and / or multiple embodiments thereof, R 1 H is H.

[0058] In one embodiment and / or multiple embodiments thereof, R 2 The group is selected from H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5.

[0059] In one embodiment and / or multiple embodiments thereof, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, and S-(halo)5.

[0060] In one embodiment and / or multiple embodiments thereof, R 2The group is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl.

[0061] In one embodiment and / or multiple embodiments thereof, R 2 The group is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl.

[0062] In one embodiment and / or multiple embodiments thereof, R 2 The group is selected from the group consisting of H, F, Cl, Br, CN, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0063] In one embodiment and / or multiple embodiments thereof, R 2 The group is selected from the group consisting of H, F, Cl, CN, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0064] In one embodiment and / or multiple embodiments thereof, R 2 The element is selected from the group consisting of H, F, Cl, CN, CH3, CHF2, and CF3.

[0065] In one embodiment and / or multiple embodiments thereof, R 2 It is selected from the group consisting of H, F, and Cl, preferably R 2 It is either F or Cl.

[0066] In one embodiment and / or multiple embodiments thereof, R 3The group is selected from H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5.

[0067] In one embodiment and / or multiple embodiments thereof, R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, and S-(halo)5.

[0068] In one embodiment and / or multiple embodiments thereof, R 3 The element is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy.

[0069] In one embodiment and / or multiple embodiments thereof, R 3 The group is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0070] In one embodiment and / or multiple embodiments thereof, R 3 The element is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0071] In one embodiment and / or multiple embodiments thereof, R 3 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 3is selected from the group consisting of H, F, Cl, Br, and CHF2.

[0072] In one embodiment and / or multiple embodiments of the present invention, R 4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5.

[0073] In one embodiment and / or multiple embodiments of the present invention, R 4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, and S-(halo)5.

[0074] In one embodiment and / or multiple embodiments of the present invention, R 4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy.

[0075] In one embodiment and / or multiple embodiments of the present invention, R 4 is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0076] In one embodiment and / or multiple embodiments of the present invention, R 4 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2, and CF3, and preferably, R 4is selected from the group consisting of H, F, and Cl, and more preferably, R 4 is F or Cl.

[0077] In one embodiment and / or multiple embodiments of the present invention, R 5 is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy.

[0078] In one embodiment and / or multiple embodiments of the present invention, R 5 is selected from the group consisting of H, F, Cl, Br, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy.

[0079] In one embodiment and / or multiple embodiments of the present invention, R 5 is selected from the group consisting of H, F, Cl, Br, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0080] In one embodiment and / or multiple embodiments of the present invention, R 5 is selected from the group consisting of H, F, and Cl.

[0081] In one embodiment and / or multiple embodiments of the present invention, R 5 is H.

[0082] In one embodiment and / or multiple embodiments of the present invention, R 6 and R 9 are each selected from the group consisting of H, CH3, and CH2CH3.

[0083] In one embodiment and / or multiple embodiments of the present invention, R 6 and R 9 are each selected from the group consisting of H and CH3.

[0084] In one embodiment and / or multiple embodiments thereof, R 6 and R 9 These are H, respectively.

[0085] In one embodiment and / or multiple embodiments thereof, R 7 and R 8 Each is selected from the group consisting of Cl and Br.

[0086] In one embodiment and / or multiple embodiments thereof, R 7 and R 8 These are both Cl.

[0087] In one embodiment and / or multiple embodiments thereof, R 10 The element is selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl.

[0088] In one embodiment and / or multiple embodiments thereof, R 10 The element is selected from the group consisting of H and (C1-C6) alkyl groups.

[0089] In one embodiment and / or multiple embodiments thereof, R 10 The group is selected from the group consisting of H and CH3.

[0090] In one embodiment and / or multiple embodiments thereof, R 10 H is H.

[0091] In one embodiment and / or multiple embodiments thereof, R 11 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy.

[0092] In one embodiment and / or multiple embodiments thereof, R 11 The element is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0093] In one embodiment and / or multiple embodiments thereof, R 11 The group is selected from the group consisting of H, F, Cl, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0094] In one embodiment and / or multiple embodiments thereof, R 11 The group is selected from H, F, Cl, CH3, and CF3.

[0095] In one embodiment and / or multiple embodiments thereof, R 11 H is H.

[0096] In one embodiment and / or multiple embodiments thereof, R 12 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy.

[0097] In one embodiment and / or multiple embodiments thereof, R 12 The element is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy.

[0098] In one embodiment and / or multiple embodiments thereof, R 12 The element is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0099] In one embodiment and / or multiple embodiments thereof, R 12The group is selected from H, F, Cl, CH3, and CF3.

[0100] In one embodiment and / or multiple embodiments thereof, R 13 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy.

[0101] In one embodiment and / or multiple embodiments thereof, R 13 The element is selected from the group consisting of H, F, Cl, Br, I, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy.

[0102] In one embodiment and / or multiple embodiments thereof, R 13 The group is selected from H, F, Cl, Br, CH3, OCH3, and CF3.

[0103] In one embodiment and / or multiple embodiments thereof, R 13 The group is selected from the group consisting of H, Cl, F, CH3, and OCH3.

[0104] In one embodiment and / or multiple embodiments thereof, R 13 It is either Cl or F.

[0105] In one embodiment and / or multiple embodiments thereof, R 14 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy.

[0106] In one embodiment and / or multiple embodiments thereof, R 14The group is selected from the group consisting of H, F, Cl, Br, I, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl.

[0107] In one embodiment and / or multiple embodiments thereof, R 14 The group is selected from H, F, Cl, CH3, and CF3.

[0108] In one embodiment and / or multiple embodiments thereof, R 14 This is selected from the group consisting of H, F, or Cl.

[0109] In one embodiment and / or multiple embodiments thereof, R 14 is H or F, preferably H.

[0110] In one embodiment and / or multiple embodiments thereof, R 15 This is selected from the group consisting of H, (C1-C6) alkyl, and (C2-C6) alkenyl.

[0111] In one embodiment and / or multiple embodiments thereof, R 15 This is selected from the group consisting of H and (C1-C6) alkyl groups.

[0112] In one embodiment and / or multiple embodiments thereof, R 15 The group is selected from the group consisting of H and CH3.

[0113] In one embodiment of the present invention and / or in some of the present inventions, Q 1 and Q 2 It is O.

[0114] In one embodiment and / or multiple embodiments thereof, R 16(C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8) Selected from the group consisting of alkyl-S(O)2-(C1~C8)alkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-NH2, and heterocyclic compounds.

[0115] In one embodiment and / or multiple embodiments thereof, R 16 In each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, (C3-C8)cycloalkyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, (C1-C8)haloalkyl, C(O)O(C1-C8)alkyl, oxoimidazolidinyl, furanyl, and pyrazolyl.

[0116] In one embodiment and / or multiple embodiments thereof, R 16In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl.

[0117] In one embodiment and / or multiple embodiments thereof, R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, and C(=O)(C1-C4) alkyl(C1-C4) alkoxy.

[0118] In one embodiment and / or multiple embodiments thereof, R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, (C=O)NH(C1-C4) alkyl, and (C=O)NH(C1-C4) haloalkyl.

[0119] In one embodiment and / or multiple embodiments thereof, R 16In this, the (C3-C8)cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, and (C=O)NH(C1-C4)alkyl.

[0120] In one embodiment and / or multiple embodiments thereof, R 16 In this, the (C3-C8)cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, and (C=O)NH(C1-C4)alkyl.

[0121] In one embodiment and / or multiple embodiments thereof, R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, and CN.

[0122] In one embodiment and / or multiple embodiments thereof, R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, and (C2-C8) alkynyl.

[0123] In one embodiment and / or multiple embodiments thereof, R 16The group is selected from the group consisting of (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl(C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, and (C1~C8)alkyl-O-(C1~C8)haloalkyl.

[0124] In one embodiment and / or multiple embodiments thereof, R 16 The group is selected from the group consisting of (C1-C8)alkyl, (C3-C8)cycloalkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)haloalkyl, and (C1-C8)alkyl-O-(C1-C8)haloalkyl.

[0125] In one embodiment and / or multiple embodiments thereof, R 16 The group is selected from the group consisting of (C1-C8) alkyl, (C3-C8) cycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, and (C1-C8) haloalkyl.

[0126] In one embodiment and / or multiple embodiments thereof, R 16 In each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, C(O)O(C1~C8)alkyl, oxoimidazolidinyl, and furanyl.

[0127] In one embodiment and / or multiple embodiments thereof, R 16 The group is selected from the group consisting of (C1-C8) alkyl, (C3-C8) cycloalkyl, and (C1-C8) haloalkyl.

[0128] In one embodiment and / or multiple embodiments thereof, R 16 In each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl.

[0129] In one embodiment and / or multiple embodiments thereof, R 16 In this, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, and (C1-C8)alkoxy.

[0130] In one embodiment and / or multiple embodiments thereof, R 16 In each alkyl, (C3-C8)cycloalkyl, and haloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl.

[0131] In one embodiment and / or multiple embodiments thereof, R 16CH2, CH2CH2, CH2CH2CH2, CH2CH2CH2CH2, CH2CH2CH2OCH2CH2, CH3, CH2CH3, CH2CH2CH3, CH2CH2CH2CH3, CH2CH2CH2CH2CH2CH3, CH2CH2CH2CH2CH2CH3, CH2CH(CH3)2, cyclopropyl, cyclobutyl, CH2cyclopropyl, CH2CH2cyclopropyl, CH2cyclobutyl, CH2phenyl, CH2CH2phenyl, CH2C=CH, CH2C=CH, CH2cf3, CH2CH2F, CH2CHF2, CH(CH3)cf3, C(CH3)2cf3, CH2CH2cf3, CH2cf2cf3, CH2CH2CH2Cl, CH2CH2CH2C Selected from the group consisting of F3, CH2CH2CF2CF3, CH2CF2CF2CF3, CH2CH2CH2CH2F, CH2CH2SCH3, CH2CH2CH2SCH3, CH(CH3)CH2SCH2CH2CF3, CH2CH2S(O)CH3, CH(CH3)CH2S(O)CH2CH2CF3, CH2CH2S(O)2CH3, CH(CH3)CH2S(O)2CH2CH2CF3, C(CH3)2CH2S(O)2CH3, offyl, OCH2CH=CH2, OCH2cyclopropyl, OCH2phenyl, CH2CH2OCH2cyclopropyl, CH2CH2CH2OCH2CF3, CH2C(=O)NHCH2CF3, or CH2CH2NHC(=O)CH3.

[0132] In one embodiment and / or multiple embodiments thereof, R 16 In each of these, CH2, CH2CH2, CH2CH2CH2, CH2CH2CH2CH2, cyclopropyl, cyclobutyl, and phenyl may be substituted with one or more substituents selected from the group consisting of F, Cl, CN, C(CH3)3, CF3, OCH3, OCH2CH3, N(CH3)2, and pyridinyl.

[0133] In one embodiment and / or multiple embodiments thereof, R 16CH3, CH2CH3, CH2CH2CH3, CH2CH2CH2CH3, CH2CH2CH2CH2CH3, CH2CH2CH2CH2CH2CH3, CH2CH(CH3)2, cyclopropyl, cyclopropyl~CN, CH2C=CH, CH2C=CH, CH2CF3, CH2CHF2, CH2CH2F, CH(CH3)CF3, C(CH3)2CF3, CH2CH2CF3, CH2CF2CF3, CH2CH2CH2Cl, CH2CH2CH2CF3, CH2 The group is selected from CH2CF2CF3, CH2CH2CH2SCH3, CH2CF2CF2CF3, CH2CH2CH2CH2F, CH2CH2SCH3, CH(CH3)CH2SCH2CH2CF3, CH2CH2S(O)CH3, CH(CH3)CH2S(O)2CH2CH2CF3, CH(CH3)CH2S(O)CH2CH2CF3, CH2CH2S(O)2CH3, C(CH3)2CH2S(O)2CH3, and CH2CH2CH2OCH2CF3.

[0134] In one embodiment and / or multiple embodiments thereof, R 16 The group is selected from the group consisting of CH3, CH2CH3, CH2CH(CH3)2, cyclopropyl~CN, CH2CF3, CH2CHF2, CH2CH2F, CH2CH2CF3, CH2CF2CF3, CH(CH3)CF3, C(CH3)2CF3, and CH2CH2CH2Cl.

[0135] In one embodiment and / or multiple embodiments thereof, R 16 The group is selected from the group consisting of CH3, CH2CH3, CH2CH(CH3)2, CH2CF3, CH2CH2F, CH2CH2CF3, CH(CH3)CF3, C(CH3)2CF3, and CH2CH2CH2Cl.

[0136] In one embodiment and / or multiple embodiments thereof, R 16 The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide. Here, R 16 Each (C3-C8) cycloalkyl and heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl.

[0137] In one embodiment and / or multiple embodiments thereof, R 16 The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide.

[0138] In one embodiment and / or multiple embodiments thereof, R 16 The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide.

[0139] In one embodiment and / or multiple embodiments thereof, R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, (C=O)NH(C1-C4)alkyl, (C=O)NH(C1-C4)haloalkyl, and C(=O)(C1-C4)alkyl(C1-C4)alkoxy.

[0140] In one embodiment and / or multiple embodiments thereof, R 16 The heterocycle is selected from the group consisting of azetidinyl, oxetanyl, and tetrahydrofuranyl.

[0141] In one embodiment and / or multiple embodiments thereof, R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, (C=O)NH(C1-C4)alkyl, (C=O)NH(C1-C4)haloalkyl, and C(=O)(C1-C4)alkyl(C1-C4)alkoxy.

[0142] In one embodiment and / or multiple embodiments thereof, R 16 The heterocycle is selected from the group consisting of azetidinyl, oxetanyl, and tetrahydrofuranyl.

[0143] In one embodiment and / or multiple embodiments thereof, R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, and (C1-C4) haloalkyl.

[0144] In one embodiment and / or multiple embodiments thereof, R 16 The heterocycle is selected from the group consisting of oxetanyl and tetrahydrofuranyl.

[0145] In one embodiment and / or multiple embodiments thereof, R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, and (C1-C4) haloalkyl.

[0146] In one embodiment and / or multiple embodiments thereof, R 16 The heterocycle is selected from the group consisting of azetidinyl, morpholinyl, oxetanyl, oxotetrahydrofuranylpyranyl, tetrahydrothiophenyl, thietanyl, thietanyl oxide, and thietanyl dioxide.

[0147] In one embodiment and / or multiple embodiments thereof, R 16 The (C3-C8) cycloalkyl group is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0148] In one embodiment and / or multiple embodiments thereof, R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, CN, C≡CH, CH=CH2, C(=O)OC(CH3)3, and C(=O)CF3.

[0149] In one embodiment and / or multiple embodiments thereof, R 16 The compound is selected from the group consisting of cyclopropyl, cyclobutyl, azetidinil, oxetanil, and oxotetrahydrofuranil.

[0150] In one embodiment and / or multiple embodiments thereof, R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, CN, C≡CH, C(=O)OC(CH3)3, and C(=O)CF3.

[0151] In one embodiment and / or multiple embodiments thereof, R 16 The compound is selected from the group consisting of cyclopropyl, cyclobutyl, azetidinil, oxetanil, and oxotetrahydrofuranil.

[0152] In one embodiment and / or multiple embodiments thereof, R 16Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, and CN.

[0153] In one embodiment of the present invention and / or in some of the present embodiments, R 1 It is selected from the group consisting of H, F, and Cl; R 2 It is selected from the group consisting of H, F, Cl, Br, CH3, and CF3; R 3 It is selected from the group consisting of H, F, Cl, CH3, and CHF2, CF3, OCF3; R 4 It is selected from the group consisting of H, F, Cl, Br, CH3, and CF3; R 5 H is; R 6 H is; R 7 It is selected from the group consisting of Cl and Br; R 8 It is selected from the group consisting of Cl and Br; R 9 , R 10 , and R 11 H is; R 12 It is selected from the group consisting of H, F, Cl, Br, and CH3; R 13 It is selected from the group consisting of H, F, Cl, CH3, and CF3; R 14 is either H or F; R 15 It is selected from the group consisting of H and CH3; Q1 and Q2 are both O.

[0154] In one embodiment of the present invention and / or in some of the embodiments thereof, R 1 H is; R 2 It is selected from the group consisting of H, F, Cl, and CH3; R 3It is selected from the group consisting of H, F, Cl, CH3, and CHF2; R 4 It is selected from the group consisting of H, F, Cl, Br, CH3, CHF2, and CF3; R 5 H is; R 6 H is; R 7 Cl is; R 8 Cl is; R 9 , R 10 , and R 11 H is; R 12 It is selected from the group consisting of H, F, Cl, Br, and CH3; R 13 It is selected from the group consisting of F, Cl, and CH3; R 14 is either H or F; R 15 It is selected from the group consisting of H and CH3; Q1 and Q2 are both O.

[0155] In one embodiment of the present invention and / or in some of the embodiments thereof, R 1 H is; R 2 It is selected from the group consisting of H, F, and Cl; R 3 It is selected from the group consisting of H, F, and Cl; R 4 It is selected from the group consisting of H, F, and Cl; R 5 H is; R 6 H is; R 7 Cl is; R 8 Cl is; R 9 , R 10 , and R 11 H is; R 12It is selected from the group consisting of H and F; R 13 It is selected from the group consisting of F and Cl; R 14 H is; R 15 H is; Q1 and Q2 are both O.

[0156] In one embodiment of the present invention and / or in some of its embodiments, at least one of the following conditions is met: a)R 1 This is selected from the group consisting of H, F, and Cl; b)R 2 This is selected from the group consisting of H, F, Cl, Br, CH3, and CHF2; c)R 3 This is selected from the group consisting of H, F, Cl, CH3, and CHF2, CF3, and OCF3; d)R 4 This is selected from the group consisting of H, F, Cl, Br, CH3, and CF3; e)R 5 H is; f)R 6 H is; g)R 7 It is selected from the group consisting of Cl and Br; h)R 8 It is selected from the group consisting of Cl and Br; i)R 9 , R 10 , and R 11 H is; j)R 12 The element is selected from the group consisting of H, F, Cl, Br, and CH3; k)R 13 This is selected from the group consisting of H, F, Cl, CH3, and CF3; l)R 14 This is selected from the group consisting of H, Cl, and F; m)R 15 This is selected from the group consisting of H and CH3; n) Q1 and Q2 are O.

[0157] In one embodiment and / or multiple embodiments thereof, R 1 It is selected from the group consisting of H, F, and Cl, and satisfies at least one of the following conditions: a)R 2 This is selected from the group consisting of H, F, Cl, Br, CH3, and CHF2; b)R 3 This is selected from the group consisting of H, F, Cl, CH3, and CHF2, CF3, and OCF3; c)R 4 This is selected from the group consisting of H, F, Cl, Br, CH3, and CF3; d)R 5 H is; e)R 6 H is; f)R 7 It is selected from the group consisting of Cl and Br; g)R 8 It is selected from the group consisting of Cl and Br; h)R 9 , R 10 , and R 11 H is; i)R 12 The element is selected from the group consisting of H, F, Cl, Br, and CH3; j)R 13 This is selected from the group consisting of H, F, Cl, CH3, and CF3; k)R 14 This is selected from the group consisting of H, Cl, and F; l)R 15 This is selected from the group consisting of H and CH3; m) Q1 and Q2 are O.

[0158] In one embodiment and / or multiple embodiments thereof, R 6 H is R 7 It is selected from the group consisting of Cl and Br, and R 8 It is selected from the group consisting of Cl and Br, and R 9 , R 10 , and R 11H is such that at least one of the following conditions is met: a)R 1 This is selected from the group consisting of H, F, and Cl; b)R 2 This is selected from the group consisting of H, F, Cl, Br, CH3, and CHF2; c)R 3 This is selected from the group consisting of H, F, Cl, CH3, and CHF2, CF3, and OCF3; d)R 4 This is selected from the group consisting of H, F, Cl, Br, CH3, and CF3; e)R 5 H is; f)R 12 The element is selected from the group consisting of H, F, Cl, Br, and CH3; g)R 13 This is selected from the group consisting of H, F, Cl, CH3, and CF3; h)R 14 This is selected from the group consisting of H, Cl, and F; i)R 15 This is selected from the group consisting of H and CH3; j) Q1 and Q2 are O.

[0159] In one embodiment of the present invention and / or in some of its embodiments, at least one of the following conditions is met: a)R 1 This is selected from the group consisting of H, F, and Cl; b)R 2 This is selected from the group consisting of H, F, and Cl; c)R 3 This is selected from the group consisting of H, F, and Cl; d)R 4 This is selected from the group consisting of H, F, and Cl; e)R 5 H is; f)R 6 H is; g)R 7 It is selected from the group consisting of Cl; h)R 8It is selected from the group consisting of Cl; i)R 9 , R 10 , and R 11 H is; j)R 12 This is selected from the group consisting of H, F, and Cl; k)R 13 This is selected from the group consisting of F and Cl; l)R 14 This is selected from the group consisting of H, Cl, and F; m)R 15 It is selected from the group consisting of H; n) Q1 and Q2 are O.

[0160] In one embodiment and / or multiple embodiments thereof, R 1 It is selected from the group consisting of H, F, and Cl, and satisfies at least one of the following conditions: a)R 2 This is selected from the group consisting of H, F, and Cl; b)R 3 This is selected from the group consisting of H, F, and Cl; c)R 4 This is selected from the group consisting of H, F, and Cl; d)R 5 H is; e)R 6 H is; f)R 7 It is selected from the group consisting of Cl; g)R 8 It is selected from the group consisting of Cl; h)R 9 , R 10 , and R 11 H is; i)R 12 This is selected from the group consisting of H, F, and Cl; j)R 13 This is selected from the group consisting of F and Cl; k)R 14 This is selected from the group consisting of H, Cl, and F; l)R 15It is selected from the group consisting of H; m) Q1 and Q2 are O.

[0161] In one embodiment and / or multiple embodiments thereof, R 6 H is R 7 is selected from the group consisting of Cl, and R 8 is selected from the group consisting of Cl, and R 9 , R 10 , and R 11 H is such that at least one of the following conditions is met: a)R 1 This is selected from the group consisting of H, F, and Cl; b)R 2 This is selected from the group consisting of H, F, and Cl; c)R 3 This is selected from the group consisting of H, F, and Cl; d)R 4 This is selected from the group consisting of H, F, and Cl; e)R 5 H is; f)R 12 This is selected from the group consisting of H, F, and Cl; g)R 13 This is selected from the group consisting of F and Cl; h)R 14 This is selected from the group consisting of H, Cl, and F; i)R 15 It is selected from the group consisting of H; j) Q1 and Q2 are O.

[0162] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (II)

[0163] [ka]

[0164] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 3 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 4H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 5 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 6 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 7 It is selected from the group consisting of H, F, Cl, Br, and I; R 8 It is selected from the group consisting of F, Cl, Br, and I; R 9 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 10This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 12 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 13 H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and triazolyl; R 14H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 15 It is selected from the group consisting of H, (C1-C6) alkyl, and (C2-C6) alkenyl; R 16 These include (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkylphenyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, O-phenyl, O-(C2~C8)alkenyl, O-(C1~C8)alkyl(C3~C8)cycloalkyl, O-(C Selected from the group consisting of (C1-C8) alkylphenyl, (C1-C8)alkyl-O-(C1-C8)alkyl(C3-C8)cycloalkyl, (C1-C8)alkyl-O-(C1-C8)haloalkyl, (C1-C8)alkyl-C(=O)NH-(C1-C8)haloalkyl, (C1-C8)alkyl-NHC(O)-(C1-C8)alkyl, (C1-C8)alkyl-S-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-NH2 and heterocyclic compounds. Here, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, haloalkyl, and phenyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, N((C1~C8)alkyl)2, C(O)O(C1~C8)alkyl, benzothioenyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl. The heterocycle is selected from the group consisting of azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinol, and Each (C3-C8) cycloalkyl and heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl; R 15 and R 16 Together, they can optionally form a 2- to 5-membered saturated or unsaturated hydrocarbyl bond which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen. Here, the hydrocarbyl bond may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NH2, and NO2; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0165] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (II)

[0166] [ka]

[0167] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 4This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 5 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H, CH3, and CH2CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl; R 12 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 13 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 14This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 15 It is selected from the group consisting of H, (C1-C6) alkyl, and (C2-C6) alkenyl; R 16 (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8) Selected from the group consisting of alkyl-S(O)2-(C1~C8)alkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-NH2, and heterocyclic compounds. Here, R 16 Each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, C(O)O(C1~C8)alkyl, oxoimidazolidinyl, furanyl, and pyrazolyl. R 16Each (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl. R 16 The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide. R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, (C=O)NH(C1-C4)alkyl, (C=O)NH(C1-C4)haloalkyl, and C(=O)(C1-C4)alkyl(C1-C4)alkoxy; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0168] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (II)

[0169] [ka]

[0170] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 4 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 5 This is selected from the group consisting of H, F, Cl, Br, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H and CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H and CH3; preferably R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 13 It is selected from the group consisting of H, F, Cl, Br, CH3, OCH3, and CF3; R 14This is selected from the group consisting of H, F, Cl, Br, I, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 15 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 16 This is selected from the group consisting of (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl(C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, and (C1~C8)alkyl-O-(C1~C8)haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, (C=O)NH(C1-C4) alkyl, and (C=O)NH(C1-C4) haloalkyl; Q 1 , and Q 2 It is O.

[0171] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (II)

[0172] [ka]

[0173] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 4 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 5 It is selected from the group consisting of H, F, Cl, Br, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, CH3, and CF3; R 13 It is selected from the group consisting of H, F, Cl, CH3, and OCH3; R 14 It is selected from the group consisting of H, F, or Cl; R 15 It is selected from the group consisting of H and CH3; R 16 This is selected from the group consisting of (C1-C8)alkyl, (C3-C8)cycloalkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)haloalkyl, and (C1-C8)alkyl-O-(C1-C8)haloalkyl. Here, each alkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. (C3-C8)cycloalkyl groups may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, and (C=O)NH(C1-C4)alkyl groups; Q 1 , and Q 2 It is O.

[0174] In one embodiment of the present invention and / or in some of its embodiments, the present invention relates to formula (III)

[0175] [ka]

[0176] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 3 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 4H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 5 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 6 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 7 It is selected from the group consisting of H, F, Cl, Br, and I; R 8 It is selected from the group consisting of F, Cl, Br, and I; R 9 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 10This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 12 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 13 H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and triazolyl; R 14H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 16 These include (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkylphenyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, O-phenyl, O-(C2~C8)alkenyl, O-(C1~C8)alkyl(C3~C8)cycloalkyl, O-(C Selected from the group consisting of (C1-C8) alkylphenyl, (C1-C8)alkyl-O-(C1-C8)alkyl(C3-C8)cycloalkyl, (C1-C8)alkyl-O-(C1-C8)haloalkyl, (C1-C8)alkyl-C(=O)NH-(C1-C8)haloalkyl, (C1-C8)alkyl-NHC(O)-(C1-C8)alkyl, (C1-C8)alkyl-S-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-NH2 and heterocyclic compounds. Here, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, haloalkyl, and phenyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, N((C1~C8)alkyl)2, C(O)O(C1~C8)alkyl, benzothioenyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl. The heterocycle is selected from the group consisting of azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinol, and Each (C3-C8) cycloalkyl and heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0177] In one embodiment of the present invention and / or in some of its embodiments, the present invention relates to formula (III)

[0178] [ka]

[0179] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 4 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 5This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H, CH3, and CH2CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl; R 12 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 13 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 14 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 16(C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8) Selected from the group consisting of alkyl-S(O)2-(C1~C8)alkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-NH2, and heterocyclic compounds. Here, R 16 Each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, C(O)O(C1~C8)alkyl, oxoimidazolidinyl, furanyl, and pyrazolyl. R 16 Each (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl. R 16The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide. R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, (C=O)NH(C1-C4)alkyl, (C=O)NH(C1-C4)haloalkyl, and C(=O)(C1-C4)alkyl(C1-C4)alkoxy; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0180] In one embodiment of the present invention and / or in some of its embodiments, the present invention relates to formula (III)

[0181] [ka]

[0182] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 4This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 5 This is selected from the group consisting of H, F, Cl, Br, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H and CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H and CH3; preferably R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 13 It is selected from the group consisting of H, F, Cl, Br, CH3, OCH3, and CF3; R 14 This is selected from the group consisting of H, F, Cl, Br, I, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 16 This is selected from the group consisting of (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl(C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, and (C1~C8)alkyl-O-(C1~C8)haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, (C=O)NH(C1-C4) alkyl, and (C=O)NH(C1-C4) haloalkyl; Q 1 , and Q 2 It is O.

[0183] In one embodiment of the present invention and / or in some of its embodiments, the present invention relates to formula (III)

[0184] [ka]

[0185] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 4 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 5 It is selected from the group consisting of H, F, Cl, Br, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, CH3, and CF3; R 13 It is selected from the group consisting of H, F, Cl, CH3, and OCH3; R 14 It is selected from the group consisting of H, F, or Cl; R 16 This is selected from the group consisting of (C1-C8)alkyl, (C3-C8)cycloalkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)haloalkyl, and (C1-C8)alkyl-O-(C1-C8)haloalkyl. Here, each alkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. Here, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, and (C=O)NH(C1-C4) alkyl; Q 1 , and Q 2 It is O.

[0186] In one embodiment of the present invention and / or in some of its embodiments, the present invention relates to formula (III)

[0187] [ka]

[0188] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 is selected from the group consisting of H, F, Cl, CN, CH3, CHF2, and CF3, preferably R 2 is selected from the group consisting of H, F, and Cl, and preferably R 2 is F or Cl; R 3 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 3 It is selected from the group consisting of H, F, Cl, Br, and CHF2; R 4 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 4 is selected from the group consisting of H, F, and Cl, and more preferably R 4 is F or Cl; R 5 It is selected from the group consisting of H, F, and Cl, preferably R 5 H is; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, CH3, and CF3; R 13 is either Cl or F; R 14 is H or F, preferably H; R 16This is selected from the group consisting of (C1-C8) alkyl, (C3-C8) cycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, and (C1-C8) haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, and (C1-C8)alkoxy. Here, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, and (C2-C8) alkynyl; Q 1 , and Q 2 It is O.

[0189] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (IV)

[0190] [ka]

[0191] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 3 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 4H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 5 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 6 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 7 It is selected from the group consisting of H, F, Cl, Br, and I; R 8 It is selected from the group consisting of F, Cl, Br, and I; R 9 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 10This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 13 H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and triazolyl; R 14 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 15 It is selected from the group consisting of H, (C1-C6) alkyl, and (C2-C6) alkenyl; R 16These include (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkylphenyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, O-phenyl, O-(C2~C8)alkenyl, O-(C1~C8)alkyl(C3~C8)cycloalkyl, O-(C Selected from the group consisting of (C1-C8) alkylphenyl, (C1-C8)alkyl-O-(C1-C8)alkyl(C3-C8)cycloalkyl, (C1-C8)alkyl-O-(C1-C8)haloalkyl, (C1-C8)alkyl-C(=O)NH-(C1-C8)haloalkyl, (C1-C8)alkyl-NHC(O)-(C1-C8)alkyl, (C1-C8)alkyl-S-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-NH2 and heterocyclic compounds. Here, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, haloalkyl, and phenyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, N((C1~C8)alkyl)2, C(O)O(C1~C8)alkyl, benzothioenyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl. The heterocycle is selected from the group consisting of azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinol, and Each (C3-C8) cycloalkyl and heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl; R 15 and R 16 Together, they can optionally form a 2- to 5-membered saturated or unsaturated hydrocarbyl bond which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen. Here, the hydrocarbyl bond may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NH2, and NO2; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0192] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (IV)

[0193] [ka]

[0194] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 4 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 5This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H, CH3, and CH2CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl; R 13 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 14 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 15 It is selected from the group consisting of H, (C1-C6) alkyl, and (C2-C6) alkenyl; R 16(C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8) Selected from the group consisting of alkyl-S(O)2-(C1~C8)alkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-NH2, and heterocyclic compounds. Here, R 16 Each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, C(O)O(C1~C8)alkyl, oxoimidazolidinyl, furanyl, and pyrazolyl. R 16 Each (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl. R 16The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide. R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, (C=O)NH(C1-C4)alkyl, (C=O)NH(C1-C4)haloalkyl, and C(=O)(C1-C4)alkyl(C1-C4)alkoxy; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0195] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (IV)

[0196] [ka]

[0197] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 4This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 5 This is selected from the group consisting of H, F, Cl, Br, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H and CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H and CH3; preferably R 10 H is; R 13 It is selected from the group consisting of H, F, Cl, Br, CH3, OCH3, and CF3; R 14 This is selected from the group consisting of H, F, Cl, Br, I, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 15 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 16 This is selected from the group consisting of (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl(C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, and (C1~C8)alkyl-O-(C1~C8)haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, (C=O)NH(C1-C4) alkyl, and (C=O)NH(C1-C4) haloalkyl; Q 1 , and Q 2 It is O.

[0198] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (IV)

[0199] [ka]

[0200] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 4 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 5 It is selected from the group consisting of H, F, Cl, Br, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 13 It is selected from the group consisting of H, F, Cl, CH3, and OCH3; R 14 It is selected from the group consisting of H, F, or Cl; R 15 It is selected from the group consisting of H and CH3; R 16 This is selected from the group consisting of (C1-C8)alkyl, (C3-C8)cycloalkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)haloalkyl, and (C1-C8)alkyl-O-(C1-C8)haloalkyl. Here, each alkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. Here, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, and (C=O)NH(C1-C4) alkyl; Q 1 , and Q 2 It is O.

[0201] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (IV)

[0202] [ka]

[0203] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 is selected from the group consisting of H, F, Cl, CN, CH3, CHF2, and CF3, preferably R 2 is selected from the group consisting of H, F, and Cl, and preferably R 2 is F or Cl; R 3 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 3 It is selected from the group consisting of H, F, Cl, Br, and CHF2; R 4 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 4 is selected from the group consisting of H, F, and Cl, and more preferably R 4 is F or Cl; R 5 It is selected from the group consisting of H, F, and Cl, preferably R 5 H is; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 13 is either Cl or F; R 14 is H or F, preferably H; R 15 H is; R 16This is selected from the group consisting of (C1-C8) alkyl, (C3-C8) cycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, and (C1-C8) haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, and (C1-C8)alkoxy. Here, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, and (C2-C8) alkynyl; Q 1 , and Q 2 It is O.

[0204] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (V)

[0205] [ka]

[0206] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 3 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 4H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 5 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 6 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 7 It is selected from the group consisting of H, F, Cl, Br, and I; R 8 It is selected from the group consisting of F, Cl, Br, and I; R 9 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 10This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 12 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 13 H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and triazolyl; R 15 It is selected from the group consisting of H, (C1-C6) alkyl, and (C2-C6) alkenyl; R 16These include (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkylphenyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, O-phenyl, O-(C2~C8)alkenyl, O-(C1~C8)alkyl(C3~C8)cycloalkyl, O-(C Selected from the group consisting of (C1-C8) alkylphenyl, (C1-C8)alkyl-O-(C1-C8)alkyl(C3-C8)cycloalkyl, (C1-C8)alkyl-O-(C1-C8)haloalkyl, (C1-C8)alkyl-C(=O)NH-(C1-C8)haloalkyl, (C1-C8)alkyl-NHC(O)-(C1-C8)alkyl, (C1-C8)alkyl-S-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-NH2 and heterocyclic compounds. Here, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, haloalkyl, and phenyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, N((C1~C8)alkyl)2, C(O)O(C1~C8)alkyl, benzothioenyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl. The heterocycle is selected from the group consisting of azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinol, and Here, each (C3-C8) cycloalkyl and heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl; R 15 and R 16 Together, they can optionally form a 2- to 5-membered saturated or unsaturated hydrocarbyl bond which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen. Here, the hydrocarbyl bond may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NH2, and NO2; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0207] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (V)

[0208] [ka]

[0209] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 4 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 5This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H, CH3, and CH2CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl; R 12 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 13 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 15 It is selected from the group consisting of H, (C1-C6) alkyl, and (C2-C6) alkenyl; R 16(C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8) Selected from the group consisting of alkyl-S(O)2-(C1~C8)alkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-NH2, and heterocyclic compounds. R 16 Each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, C(O)O(C1~C8)alkyl, oxoimidazolidinyl, furanyl, and pyrazolyl. R 16 Each (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl. R 16The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide. R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, (C=O)NH(C1-C4)alkyl, (C=O)NH(C1-C4)haloalkyl, and C(=O)(C1-C4)alkyl(C1-C4)alkoxy; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0210] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (V)

[0211] [ka]

[0212] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 4This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 5 This is selected from the group consisting of H, F, Cl, Br, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H and CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H and CH3; preferably R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 13 It is selected from the group consisting of H, F, Cl, Br, CH3, OCH3, and CF3; R 15 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 16 This is selected from the group consisting of (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl(C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, and (C1~C8)alkyl-O-(C1~C8)haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, (C=O)NH(C1-C4) alkyl, and (C=O)NH(C1-C4) haloalkyl; Q 1 , and Q 2 It is O.

[0213] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (V)

[0214] [ka]

[0215] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 4 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 5 It is selected from the group consisting of H, F, Cl, Br, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, CH3, and CF3; R 13 It is selected from the group consisting of H, F, Cl, CH3, and OCH3; R 15 It is selected from the group consisting of H and CH3; R 16 This is selected from the group consisting of (C1-C8)alkyl, (C3-C8)cycloalkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)haloalkyl, and (C1-C8)alkyl-O-(C1-C8)haloalkyl. Here, each alkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. (C3-C8)cycloalkyl groups may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, and (C=O)NH(C1-C4)alkyl groups; Q 1 , and Q 2 It is O.

[0216] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (V)

[0217] [ka]

[0218] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 is selected from the group consisting of H, F, Cl, CN, CH3, CHF2, and CF3, preferably R 2 is selected from the group consisting of H, F, and Cl, and preferably R 2 is F or Cl; R 3 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 3 It is selected from the group consisting of H, F, Cl, Br, and CHF2; R 4 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 4 is selected from the group consisting of H, F, and Cl, and more preferably R 4 is F or Cl; R 5 It is selected from the group consisting of H, F, and Cl, preferably R 5 H is; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, CH3, and CF3; R 13 is either Cl or F; R 15 H is; R 16This is selected from the group consisting of (C1-C8) alkyl, (C3-C8) cycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, and (C1-C8) haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, and (C1-C8)alkoxy. (C3-C8) cycloalkyl groups may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, and (C2-C8) alkynyl groups; Q 1 , and Q 2 It is O.

[0219] In one embodiment and / or several embodiments thereof, the present invention relates to formula (VI).

[0220] [ka]

[0221] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 3 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 4H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 5 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 6 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 7 It is selected from the group consisting of H, F, Cl, Br, and I; R 8 It is selected from the group consisting of F, Cl, Br, and I; R 9 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 10This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 12 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 13 H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and triazolyl; R 16These include (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkylphenyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, O-phenyl, O-(C2~C8)alkenyl, O-(C1~C8)alkyl(C3~C8)cycloalkyl, O-(C Selected from the group consisting of (C1-C8) alkylphenyl, (C1-C8)alkyl-O-(C1-C8)alkyl(C3-C8)cycloalkyl, (C1-C8)alkyl-O-(C1-C8)haloalkyl, (C1-C8)alkyl-C(=O)NH-(C1-C8)haloalkyl, (C1-C8)alkyl-NHC(O)-(C1-C8)alkyl, (C1-C8)alkyl-S-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-NH2 and heterocyclic compounds. Here, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, haloalkyl, and phenyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, N((C1~C8)alkyl)2, C(O)O(C1~C8)alkyl, benzothioenyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl. The heterocycle is selected from the group consisting of azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinol, and Each (C3-C8) cycloalkyl and heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0222] In one embodiment and / or several embodiments thereof, the present invention relates to formula (VI).

[0223] [ka]

[0224] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 4 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 5 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H, CH3, and CH2CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10is selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl; R 12 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 13 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 16 (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8) Selected from the group consisting of alkyl-S(O)2-(C1~C8)alkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-NH2, and heterocyclic compounds. Here, R 16 Each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, C(O)O(C1~C8)alkyl, oxoimidazolidinyl, furanyl, and pyrazolyl. R16 Each (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl. R 16 The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide. R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, (C=O)NH(C1-C4)alkyl, (C=O)NH(C1-C4)haloalkyl, and C(=O)(C1-C4)alkyl(C1-C4)alkoxy; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0225] In one embodiment of the present invention and / or in some of its embodiments, the present invention relates to formula (VI).

[0226] [ka]

[0227] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 4 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 5 This is selected from the group consisting of H, F, Cl, Br, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H and CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H and CH3; preferably R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 13 It is selected from the group consisting of H, F, Cl, Br, CH3, OCH3, and CF3; R 16This is selected from the group consisting of (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl(C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, and (C1~C8)alkyl-O-(C1~C8)haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, (C=O)NH(C1-C4) alkyl, and (C=O)NH(C1-C4) haloalkyl; Q 1 , and Q 2 It is O.

[0228] In one embodiment and / or several embodiments thereof, the present invention relates to formula (VI).

[0229] [ka]

[0230] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 4 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 5 It is selected from the group consisting of H, F, Cl, Br, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, CH3, and CF3; R 13 It is selected from the group consisting of H, F, Cl, CH3, and OCH3; R 16 This is selected from the group consisting of (C1-C8)alkyl, (C3-C8)cycloalkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)haloalkyl, and (C1-C8)alkyl-O-(C1-C8)haloalkyl. Here, each alkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. (C3-C8)cycloalkyl groups may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, and (C=O)NH(C1-C4)alkyl groups; Q 1 , and Q 2 It is O.

[0231] In one embodiment and / or several embodiments thereof, the present invention relates to formula (VI).

[0232] [ka]

[0233] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 is selected from the group consisting of H, F, Cl, CN, CH3, CHF2, and CF3, preferably R 2 is selected from the group consisting of H, F, and Cl, and preferably R 2 is F or Cl; R 3 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 3 It is selected from the group consisting of H, F, Cl, Br, and CHF2; R 4 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 4 is selected from the group consisting of H, F, and Cl, and more preferably R 4 is F or Cl; R 5 It is selected from the group consisting of H, F, and Cl, preferably R 5 H is; R 6 and R9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 12 It is selected from the group consisting of H, F, Cl, CH3, and CF3; R 13 is either Cl or F; R 16 This is selected from the group consisting of (C1-C8) alkyl, (C3-C8) cycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, and (C1-C8) haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, and (C1-C8)alkoxy. (C3-C8) cycloalkyl groups may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, and (C2-C8) alkynyl groups; Q 1 , and Q 2 It is O.

[0234] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (VII)

[0235] [ka]

[0236] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 3 H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 4H, F, Cl, Br, I, CN, NH2, NO2, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, (C1 Selected from the group consisting of ~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and S-(halo)5; R 5 H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2 and (C1~C6)haloalkyl-S(O)2NH2; R 6 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 7 It is selected from the group consisting of H, F, Cl, Br, and I; R 8 It is selected from the group consisting of F, Cl, Br, and I; R 9 It is selected from the group consisting of H and (C1-C6) alkyl groups; R 10This is selected from the group consisting of H, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)haloalkyl, (C1-C6)alkyl(C1-C6)alkoxy, C(=O)(C1-C6)alkyl, and (C1-C6)alkoxyC(=O)(C1-C6)alkyl; R 13 H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1~C6) alkyl, (C3~C6) cycloalkyl, (C2~C6) alkenyl, (C3~C6) cycloalkenyl, (C2~C6) alkynyl, (C1~C6) alkoxy, (C1~C6) haloalkyl, (C3~C6) halocycloalkyl, (C2~C6) haloalkenyl, (C3~C6) halocycloalkenyl, Selected from the group consisting of (C1~C6)haloalkoxy, S(C1~C6)alkyl, S(O)(C1~C6)alkyl, S(O)2(C1~C6)alkyl, S(C1~C6)haloalkyl, S(O)(C1~C6)haloalkyl, S(O)2(C1~C6)haloalkyl, (C1~C6)alkyl-S(O)2NH2, (C1~C6)haloalkyl-S(O)2NH2, and triazolyl; R 16These include (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C1~C8)alkylphenyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, O-phenyl, O-(C2~C8)alkenyl, O-(C1~C8)alkyl(C3~C8)cycloalkyl, O-(C Selected from the group consisting of (C1-C8) alkylphenyl, (C1-C8)alkyl-O-(C1-C8)alkyl(C3-C8)cycloalkyl, (C1-C8)alkyl-O-(C1-C8)haloalkyl, (C1-C8)alkyl-C(=O)NH-(C1-C8)haloalkyl, (C1-C8)alkyl-NHC(O)-(C1-C8)alkyl, (C1-C8)alkyl-S-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-(C1-C8)haloalkyl, (C1-C8)alkyl-S(O)2-NH2 and heterocyclic compounds. Here, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, haloalkyl, and phenyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, N((C1~C8)alkyl)2, C(O)O(C1~C8)alkyl, benzothioenyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl. The heterocycle is selected from the group consisting of azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinol, isoxazolidinol, morpholinyl, oxazolidinol, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinol, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinol, and Each (C3-C8) cycloalkyl and heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0237] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (VII)

[0238] [ka]

[0239] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 4 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl, (C1-C6) haloalkoxy, (C1-C6) alkyl-S(O)2NH2, and S-(halo)5; R 5 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H, CH3, and CH2CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10is selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl; R 13 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, and (C1-C6) haloalkoxy; R 16 (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl-O-(C1~C8)alkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8) Selected from the group consisting of alkyl-S(O)2-(C1~C8)alkyl, (C1~C8)alkyl-O-(C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-(C1~C8)haloalkyl, (C1~C8)alkyl-S(O)2-NH2, and heterocyclic compounds. Here, R 16 Each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, (C1~C8)alkyl, (C2~C8)alkenyl, (C2~C8)alkynyl, (C1~C8)alkoxy, (C1~C8)haloalkyl, C(O)O(C1~C8)alkyl, oxoimidazolidinyl, furanyl, and pyrazolyl. R 16Each (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, C(=O)O(C1-C4) alkyl, (C=O)NH(C1-C4) alkyl, (C=O)NH(C1-C4) haloalkyl, C(=O)(C3-C6) cyclopropyl, C(=O)(C1-C4) haloalkyl, C(=O)(C1-C4) alkyl(C1-C4) alkoxy, and (C1-C4) alkyl-morpholinyl. R 16 The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide. R 16 Each heterocycle may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, (C=O)NH(C1-C4)alkyl, (C=O)NH(C1-C4)haloalkyl, and C(=O)(C1-C4)alkyl(C1-C4)alkoxy; Q 1 and Q 2 Each is independently selected from the group consisting of O and S.

[0240] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (VII)

[0241] [ka]

[0242] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C2-C6) alkenyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 4 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 5 This is selected from the group consisting of H, F, Cl, Br, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, and (C1-C6) haloalkoxy; R 6 and R 9 These are selected from the group consisting of H and CH3, respectively; R 7 , and R 8 These are selected from the group consisting of Cl and Br; R 10 is selected from the group consisting of H and CH3; preferably R 10 H is; R 13 It is selected from the group consisting of H, F, Cl, Br, CH3, OCH3, and CF3; R 16This is selected from the group consisting of (C1~C8)alkyl, (C3~C8)cycloalkyl, (C1~C8)alkyl(C3~C8)cycloalkyl, (C2~C8)alkenyl(C2~C8)alkynyl, (C1~C8)haloalkyl, (C1~C8)alkyl-S-(C1~C8)alkyl, (C1~C8)alkyl-S(O)-(C1~C8)alkyl, (C1~C8)alkyl-S(O)2-(C1~C8)alkyl, and (C1~C8)alkyl-O-(C1~C8)haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. R 16 In this, the (C3-C8) cycloalkyl group may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH2, NO2, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C4) haloalkyl, (C=O)NH(C1-C4) alkyl, and (C=O)NH(C1-C4) haloalkyl; Q 1 , and Q 2 It is O.

[0243] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (VII)

[0244] [ka]

[0245] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, (C1-C6) alkoxy, and (C1-C6) haloalkyl; R 3 This is selected from the group consisting of H, F, Cl, Br, I, CN, NH2, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 4 It is selected from the group consisting of H, F, Cl, Br, I, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 5 It is selected from the group consisting of H, F, Cl, Br, (C1-C6) alkyl, and (C1-C6) haloalkyl; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 13 It is selected from the group consisting of H, F, Cl, CH3, and OCH3; R 16 This is selected from the group consisting of (C1-C8)alkyl, (C3-C8)cycloalkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)haloalkyl, and (C1-C8)alkyl-O-(C1-C8)haloalkyl. Here, each alkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, C(O)O(C1-C8)alkyl, and oxoimidazolidinyl. (C3-C8)cycloalkyl groups may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)haloalkyl, and (C=O)NH(C1-C4)alkyl groups; Q 1, and Q 2 It is O.

[0246] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (VII)

[0247] [ka]

[0248] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 is selected from the group consisting of H, F, Cl, CN, CH3, CHF2, and CF3, preferably R 2 is selected from the group consisting of H, F, and Cl, and preferably R 2 is F or Cl; R 3 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 3 It is selected from the group consisting of H, F, Cl, Br, and CHF2; R 4 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 4 is selected from the group consisting of H, F, and Cl, and more preferably R 4 is F or Cl; R 5 It is selected from the group consisting of H, F, and Cl, preferably R 5 H is; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 13 is either Cl or F; R16 This is selected from the group consisting of (C1-C8) alkyl, (C3-C8) cycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, and (C1-C8) haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, and (C1-C8)alkoxy. (C3-C8) cycloalkyl groups may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, and (C2-C8) alkynyl groups; Q 1 , and Q 2 It is O.

[0249] In one embodiment and / or multiple embodiments thereof, the present invention relates to formula (VII)

[0250] [ka]

[0251] With regard to the compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers thereof, and their use in methods for controlling parasitic infections of fish, in the formula, R 2 is selected from the group consisting of H, F, Cl, CN, CH3, CHF2, and CF3, preferably R 2 is selected from the group consisting of H, F, and Cl, and preferably R 2 is F or Cl; R 3 is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 3 It is selected from the group consisting of H, F, Cl, Br, and CHF2; R 4is selected from the group consisting of H, F, Cl, Br, CH3, CHF2 and CF3, preferably R 4 is selected from the group consisting of H, F, and Cl, and more preferably R 4 is F or Cl; R 5 It is selected from the group consisting of H, F, and Cl, preferably R 5 H is; R 6 and R 9 These are H, respectively; R 7 and R 8 These are Cl, respectively; R 10 H is; R 13 is either Cl or F; R 16 This is selected from the group consisting of (C1-C8) alkyl, (C3-C8) cycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, and (C1-C8) haloalkyl. Here, each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, and (C1-C8)alkoxy. (C3-C8) cycloalkyl groups may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, CN, oxo, (C1-C4) alkyl, (C2-C8) alkenyl, and (C2-C8) alkynyl groups; Q 1 , and Q 2 It is O.

[0252] Suitable compounds according to the present invention and its embodiments are those listed in the following table:

[0253] [ka]

[0254] [ka]

[0255] [ka]

[0256] [ka]

[0257] [ka]

[0258] [ka]

[0259] The following are suitable compounds with advantageous properties:

[0260] [ka]

[0261] [ka]

[0262] [ka]

[0263] Salts, solvates, N-oxides, and prodrugs Salts of the compound of formula (I) or other compounds may be advantageous for one or more of the physical properties of the salt, such as pharmaceutically stable at different temperatures and humidity; crystalline properties; and / or desirable solubility in water, oil, or other solvents. In some examples, salts may be used as aids in the isolation, purification, and / or reconstitution of the compound. Acid salts and base salts can typically be formed by mixing the compound with an acid or a base, respectively, using various known methods in the art, for example. Salts of a compound are pharmaceutically acceptable insofar as they are intended to be administered in vivo (i.e., to animals) for therapeutic benefit.

[0264] Salts may also be advantageous in the synthesis of compounds according to the present invention and / or its embodiments. For example, certain intermediates may be advantageously used in the form of their salts in the compound preparation process according to the present invention and / or its embodiments.

[0265] Generally, acid addition salts can be prepared by reacting a free base compound with a nearly stoichiometric amount of an inorganic or organic acid. Non-limiting examples of inorganic acids that are often suitable for producing (pharmaceutically acceptable) salts include hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, carbonic acid, sulfuric acid, and phosphoric acid. Non-limiting examples of organic acids that are often suitable for producing (pharmaceutically acceptable) salts generally include, for example, organic acids of the classes aliphatic, alicyclic, aromaticaliphatic, heterocyclic, carboxylic acid, and sulfonic acid. Often preferred organic acids include cholic acid, sorbic acid, lauric acid, acetic acid, trifluoroacetic acid, formic acid, propionic acid, succinic acid, glycolic acid, gluconic acid, digluconic acid, lactic acid, malic acid, tartaric acid, citric acid, ascorbic acid, glucuronic acid, maleic acid, fumaric acid, pyruvic acid, aspartic acid, glutamic acid, aryl carboxylic acids (e.g., benzoic acid), anthranilic acid, mesylic acid, stearic acid, salicylic acid, p-hydroxybenzoic acid, phenylacetic acid, mandelic acid, embonic acid (pamoic acid), alkyl sulfonic acid (e.g., ethanesulfonic acid), aryl sulfonic acid (e.g., Examples include benzenesulfonic acid, pantothenic acid, 2-hydroxyethanesulfonic acid, sulfanilic acid, cyclohexylaminosulfonic acid, β-hydroxybutyric acid, galactaric acid, galacturonic acid, adipic acid, alginic acid, butyric acid, camphoric acid, camphorsulfonic acid, camphorsulfonic acid, cyclopentanepropionic acid, dodecyl sulfate, glycoheptanoic acid, glycerophosphate, heptanoic acid, hexanoic acid, nicotinic acid, 2-naphthasulfonic acid, oxalic acid, palmoic acid, pectinic acid, 3-phenylpropionic acid, picric acid, pivalic acid, thiocyanic acid, tosylic acid, and undecanoic acid. In some such embodiments, for example, the salt includes trifluoroacetate, mesylate, or tosylate. In other embodiments, the salt includes hydrochloride.

[0266] As an unrestricted example, amine functional groups can form salts with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, benzoic acid, citric acid, malonic acid, salicylic acid, malic acid, fumaric acid, oxalic acid, succinic acid, tartaric acid, lactic acid, gluconic acid, ascorbic acid, maleic acid, aspartic acid, benzenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, hydroxyl-methanesulfonic acid, and hydroxyethanesulfonic acid. Furthermore, as an unrestricted example, acid functional groups can form salts derived from alkali metals or alkaline earth metals, as well as salts derived from ammonia and amines. Examples of preferred cations include sodium, potassium, and magnesium.

[0267] Generally, base addition salts can be prepared by reacting a free acid compound with a nearly stoichiometric amount of an inorganic or organic base. Examples of base addition salts include metal salts and organic salts. Metal salts include, for example, alkali metal (Group Ia) salts, alkaline earth metal (Group IIa) salts, and other physiologically acceptable metal salts. Such salts can be made from aluminum, calcium, lithium, magnesium, potassium, sodium, and zinc. For example, such base addition salts can be formed by mixing a free acid compound with sodium hydroxide. Organic salts can be made from amines such as trimethylamine, diethylamine, N,N'-dibenzylethylenediamine, chloroprocaine, ethanolamine, diethanolamine, ethylenediamine, meglumine (N-methylglucamine), and procaine. Basic nitrogen-containing groups can be quaternized with agents such as C1-C6 alkyl halides (e.g., methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides), dialkyl sulfates (e.g., dimethyl sulfate, diethyl sulfate, dibutyl sulfate, and diamyl sulfate), long-chain halides (e.g., decyl, lauryl, myristyl, and stearyl chlorides, bromides, and iodides), and arylalkyl halides (e.g., benzyl bromide and phenethyl bromide).

[0268] The compound of formula (I) can be formulated into a solvent-stable complex such that the complex remains intact after the removal of the non-complexing solvent. These complexes are often called "solvates." However, it is particularly desirable to form a stable hydrate using water as the solvent.

[0269] A solvate of the compound of formula (I) or another compound may be formed, preferably in a predetermined weight proportion, by aggregation of the compound of formula (I) with solvent molecules such as water, alcohol, e.g., ethanol, aromatic solvent, e.g., toluene, ether, halogenated organic solvent, e.g., dichloromethane.

[0270] Compounds of formula (I) containing an acidic functional group can be converted into ester derivatives. These ester derivatives can then be applied in the same manner as the compounds disclosed herein are applied.

[0271] The compound of formula (I) can be prepared as various crystalline polymorphs. Polymorphism is important in the development of veterinary products because different crystalline polymorphs or structures of the same molecule can have significantly different physical properties and biological performance.

[0272] The N-oxide of the compound of formula (I), or another compound, can be formed by oxidation of the N atom of an amine or N-heterocyclic ring such as pyridine and pyrimidine with an oxidizing agent such as hydrogen peroxide or a peracid, or an inorganic oxidizing agent such as potassium peroxymonosulfate (Oxone).

[0273] The present invention also encompasses prodrug derivatives of the compound of formula (I). The term prodrug refers to a compound that is transformed in vivo to produce the parent compound of formula (I). In vivo means that this transformation can occur in the host organism and / or parasite, for example, in the treatment of parasitic infections. Various forms of prodrugs are well known in the art. For example, when the group of formula (A) represents pyridine, it is possible to form pyridinium salts, such as acyloxypyridinium salts, which can offer advantages in terms of high solubility for parenteral dosage forms, as described in SK Davidsen et al., et al., J. of Med. Chem. 37 4423-4429 (1994).

[0274] The compound of formula (I) can be prepared using different isotopes. Of particular importance is: 1 Instead of H, 2 A molecule containing H (also known as a deuterium) or 3 It is a molecule containing H (also known as tritium). The molecule in formula 1 can be prepared using different radionuclides. Of particular importance is: 14 It is a molecule containing C (also known as radioactive carbon). Deuterium, tritium or 14 Molecules of formula (I) containing C can be used in biological studies that enable tracking and half-life studies of chemical and physiological processes, as well as MoA studies. isomer Compounds of formula (I) may exist in the form of different geometric isomers or optical isomers, or different tautomers. One or more chirality centers may be present, in which case the compound of formula (I) may exist as a pure enantiomer, a mixture of enantiomers, a pure diastereomer, or a mixture of diastereomers. It will be understood by those skilled in the art that one stereoisomer may be more active than the other. Individual stereoisomers can be obtained by known selective synthetic procedures, by conventional synthetic procedures using divided starting materials, or by conventional division procedures. Double bonds may be present in the molecule, in which case the compound of formula (I) may exist as a single geometric isomer (cis or trans, E or Z) or a mixture of geometric isomers (cis and trans, E and Z). Tautomerization centers may be present. This disclosure encompasses all proportions of such isomers, tautomers, and mixtures thereof.

[0275] In some embodiments, such compounds may have two or more isomers, such as optical isomers or conformational isomers. For example, a compound may have R 16 Alkenyl or alkynyl substituents, or R 16 In the ring structure of the alkenyl or alkynyl substituent, ~CXR 3 =CR 1 R 2 The double bond can have either an (E) or (Z) configuration. In some preferred embodiments, such compounds have an (E) configuration, and in other embodiments, the compounds have a (Z) configuration. In preferred embodiments, the compounds have an (E) configuration. For example, the compound of formula (II), and the compounds in Tables A, C, and D below, exhibit an (E) configuration.

[0276] Unless otherwise specified, compound structures that do not exhibit a specific conformation are intended to encompass all possible conformational isomers of the compound, as well as fewer conformational isomers than all possible conformations. Compounds with two chiral centers have four isomers: RR-, SS-, RS-, and SR- isomers. Such compounds may exist in several forms, namely in the form of pure RR, or SS, RS, or SR isomers, or as mixtures referred to below as "enantiomer pairs" of either RR / SS or RS / SR.

[0277] Cyclopropylamide compounds can also exist as a racemic mixture of all four isomers (RR+SS+RS+SR), or as a racemic mixture of enantiomer pairs (RR / SS) or (RS / SR). The isomers (RR) and (SS) are mirror images of each other and are therefore enantiomers with the same chemical properties and melting point. (RS) and (SR) are similarly enantiomer pairs. However, the mirror images of (RR) and (SS) cannot be superimposed on (RS) and (SR). This relationship is called diastereomerism, where (RR) is the diastereomer of (RS).

[0278] Although structurally identical, isomers may have different effects in biological systems. One isomer may have specific therapeutic activity, while another isomer may not have therapeutic activity, or may have entirely different forms of biological activity.

[0279] In the compound of the present invention, cyclopropane contains two chiral centers, one bonded to a phenyl group and the other to a carboxamide group.

[0280] Surprisingly, it has been found that administering a pure or substantially pure RR-isomer of the compound according to the present invention, the embodiments described herein, or a pharmaceutically acceptable salt thereof can significantly improve parameters such as efficacy, while substantially avoiding side effects. The applicant has thus found this by administering a therapeutically effective amount of a pure or substantially pure RR-isomer of the compound according to the present invention, the embodiments described herein, or a pharmaceutically acceptable salt thereof.

[0281] Terms such as "pure RR-cyclopropylamide compound" and "pure RR-isomer of cyclopropylamide compound" refer to a cyclopropylamide compound having an optical purity of 98% by weight or more of the RR-isomer, while the total concentration (i.e., sum) of the corresponding RS-, SR-, and SS-isomers is 2% by weight or less, based on the total amount of the cyclopropylamide compound present.

[0282] Terms such as "substantially pure RR-cyclopropylamide compound" and "substantially pure RR-isomer of cyclopropylamide compound" refer to the optical purity of the RR-*cyclopropylamide compound being 80% by weight or more, meaning a concentration of 80% by weight or more of the RR-cyclopropylamide compound and a total concentration of 20% by weight or less of the corresponding RS-, SR-, and SS-isomers, based on the total amount of cyclopropylamide compound present. In a more preferred embodiment, a substantially pure RR-cyclopropylamide compound contains 90% by weight or more of the RR-cyclopropylamide compound and a total of 10% or less of the RS, SR-, and SS-isomers of the cyclopropylamide compound.

[0283] In a suitable embodiment, the compound of formula (I), carboxamide, and phenyl bonded to cyclopropane are in an R,R configuration. In this embodiment, R 1 , R 2 , R 3 , R 4 , R 5 , R 6, R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 It can be used in combination with any of the other embodiments.

[0284] In one embodiment of the present invention and / or several embodiments thereof, the parasitic organism is a sea louse.

[0285] In one embodiment of the present invention and / or several embodiments thereof, the parasite is at least one of Lepeophtheirus salmonis, Caligus celmensi, Caligus curtus, Caligus dussumieri, Caligus elongates, Caligus longicaudatus, Caligus rogercresseyi, or Caligus stromii.

[0286] In one embodiment of the present invention and / or several embodiments thereof, the parasitic organism is copepod, pre-adult or adult sea lice, or a mixed parasitic organism at various stages.

[0287] In one embodiment and / or multiple embodiments thereof, a pre-existing parasitic infestation of a fish population is treated.

[0288] In one embodiment of the present invention and / or several embodiments thereof, the parasite is an adult sea louse.

[0289] In one embodiment of the present invention and / or several embodiments thereof, the parasite is a juvenile sea louse.

[0290] In one embodiment of the present invention and / or multiple embodiments thereof, the parasitic rate in a fish population in an aquaculture facility is 0.5 to 3 parasites per fish on average, and preferably the parasite is an adult female sea louse.

[0291] In one embodiment of the present invention and / or several embodiments thereof, the method comprises administering to a fish an effective amount of a compound of formula (I) as defined in any embodiment described herein to protect the fish from parasitic and / or reparasitic infection, preferably the parasite being a pre-adult or adult sea louse.

[0292] In one embodiment of the present invention and / or several embodiments thereof, the method comprises administering an effective amount of a compound of formula (I) as defined in any embodiment described herein to a fish, wherein the time between administrations is 2 to 8 weeks, preferably 3 to 6 weeks, and more preferably about 4 weeks.

[0293] In one embodiment and / or multiple embodiments thereof, the parasite is resistant to macrocyclic lactones, organophosphates and / or pyrethroid antiparasitic agents, and preferably the parasite is a sea louse.

[0294] In one embodiment of the present invention and / or several embodiments thereof, the method comprises administering a compound of formula (I), as defined in any embodiment described herein, to fish together with a physiological agent.

[0295] In one embodiment of the present invention and / or several embodiments thereof, the method comprises administering a compound of formula (I) as defined in any embodiment described herein together with an antigen to a fish, optionally, the compound and antigen being administered together with an adjuvant.

[0296] In one embodiment of the present invention and / or several embodiments thereof, the method comprises administering a compound of formula (I) as defined in any embodiment described herein together with an additional antiparasitic agent to a fish.

[0297] In one embodiment of the present invention and / or several embodiments thereof, the method comprises administering a compound of formula (I) as defined in any embodiment described herein to a fish by oral administration, topical administration, bath treatment, or intraperitoneal or intramuscular injection.

[0298] In one embodiment of the present invention and / or several embodiments thereof, the method comprises administering a compound of formula (I) as defined in any embodiment herein by oral administration to a fish, wherein the oral administration comprises administering a medicated fish feed containing the compound and fish feed.

[0299] In one embodiment of the present invention and / or several embodiments thereof, a medicated fish feed is administered daily for 3 to 7 days.

[0300] In one embodiment of the present invention and / or several embodiments thereof, the method comprises administering a compound of formula (I) as defined in any embodiment described herein to a fish by a bath treatment, the bath treatment comprising immersion of the fish in water containing a therapeutically effective amount of the compound.

[0301] The present invention also relates to compositions comprising a compound of formula (I) as defined in any embodiment described herein and a veterinarily acceptable formulation adjuvant.

[0302] In one embodiment of the present invention and / or several embodiments thereof, the composition comprises a solvent and optionally a solubilizer.

[0303] In one embodiment of the present invention and / or several embodiments thereof, the composition is in the form of a stock solution used to form medicinal water containing an effective amount of the compound.

[0304] In one embodiment of the present invention and / or several embodiments thereof, the effective amount of the compound in the medicinal water is about 2 ppb to about 500 ppb.

[0305] In one embodiment of the present invention and / or several embodiments thereof, the method includes administering a compound to fish by immersion of the fish in a bath.

[0306] In one embodiment of the present invention and / or several embodiments thereof, the method includes administering a composition to fish by oral administration via feed.

[0307] Furthermore, the present invention relates to a premix comprising a compound of formula (I) as defined in any embodiment described herein and / or a composition described herein, wherein the premix further comprises nutrients.

[0308] In one embodiment of the present invention and / or several embodiments thereof, the premix comprises nutrients in the form of pellets, the pellets being coated with a composition comprising a compound of formula (I) as defined in any embodiment described herein, or coated with a composition described herein.

[0309] In one embodiment of the present invention and / or several embodiments thereof, the premix comprises nutrients in the form of pellets, the pellets being mixed with a composition comprising a compound of formula (I) as defined in any embodiment described herein or with a composition described herein.

[0310] Furthermore, the present invention relates to medicinal fish feed and fish feed comprising the composition or premix described herein.

[0311] The medicinal fish feed described herein is suitable for use in the methods described herein.

[0312] The present invention also relates to a kit comprising the compositions described herein and instructions for administering the compositions to fish for the control of parasitic infestations.

[0313] The present invention also relates to a kit comprising the premix described herein, instructions for preparing medicated fish feed, and instructions for administering the medicated fish feed to fish to control parasitic infestations.

[0314] The present invention also relates to a kit comprising the stock solution described herein, instructions for preparing medicinal water for bath treatment, and instructions for immersing fish to prevent parasitic infestation. definition The following definitions relate to embodiments of the present invention. definition A “parasite” is an organism that lives on or inside another organism (usually called a host) and causes harm to the host. As used herein, unless otherwise indicated, it refers to endoparasites and ectoparasites. Endoparasites are parasites that live inside the body of their host and include helminths (e.g., trematodes, tapeworms, and nematodes) and protozoa. Exoparasites are organisms that feed on or through the skin of their host. In this invention, the host animal is a fish.

[0315] As used herein, “fish” refers, unless otherwise specified, to the taxonomic classes of cartilaginous fishes (Chondrichthyes) (e.g., sharks and ray-finned fishes) and bony fishes (Osteichthyes) that live in water and have gills or mucus-covered skin, fins, and scales for respiration. This includes freshwater fish, edible fish of all ages that occur in saltwater (e.g., oceans) and brackish water, breeding fish and tank fish, pond fish and farmed fish.

[0316] Non-exclusive examples of edible fish include carp, eels, trout, whitebait, salmon, roach, rad, chub, Arctic char, sturgeon, flounder, halibut, turbot, sole, striped bass, yellowtail, grouper, cod, sole, tuna, sea bream, sea bass, gray mullet, pompano, ocean sunfish, tilapia, and catfish.

[0317] The present invention relates more particularly to marine fish, and more particularly to marine edible fish, in particular to salmon.

[0318] Within the scope of this invention, the term "salmon" is understood to include all representative species of the Salmonidae family, in particular the following species: Salmo salar (Atlantic salmon); Salmo trutta (brown trout or sea trout); Salmon gairdneri (rainbow trout); and Pacific salmon (Oncorhynchus): O. gorbuscha; O. keta; O. nekra; O. kisutch, O. tshawytscha, and O. mason; and also includes artificially propagated species such as Salvelinus spp. and Salmo clarkia.

[0319] The preferred hosts for this invention are Western salmon, Pacific salmon, and saltwater trout.

[0320] In other embodiments, the host fish is Mediterranean bass and / or sea bream. In other embodiments, the host fish is a freshwater fish such as carp and / or freshwater trout. In yet another embodiment, the fish is tilapia.

[0321] A fish population refers to a group of individual fish kept in a limited area such as a seawater tank, cage, or net. Cages and nets are moored at the seawater inlet so that daily tidal currents pass through them, ensuring a sufficient supply of oxygen and clean water.

[0322] In the case of tanks, there is a continuous flow of seawater into and out of the tank, or at least scheduled freshwater flushing, to ensure sufficient water quality and oxygen to maintain the health of the fish. In this artificial environment, the fish are fed and given medication as needed until they are mature enough to be sold as food fish or selected for further breeding.

[0323] In one embodiment of the present invention, a compound of formula (I) or a salt, enantiomer, or prodrug thereof is administered to a fish population at the end of the freshwater stage or at the start of the saltwater stage in fish farming.

[0324] According to another embodiment, the procedure is carried out while the (salmon or trout) fish are kept in seawater. Sea lice According to the present invention, the compound of formula (I) is particularly suitable for use in controlling fish-parasitic crustaceans such as sea lice. Therefore, in one embodiment, the compound of formula (I) is used to control fish-parasitic crustaceans, especially sea lice.

[0325] Sea lice are a general term given to a group of ichthyopora crustaceans, which are ectoparasitic copepods that affect fish in seawater. As used herein, unless otherwise specified, "sea lice" refers to parasitic crustaceans (copepods) within the order Siphonostomatoida that parasitize their hosts via or on the mucus, skin, and tissues.

[0326] These include the families Caligidae and Lernanthropidae. Two representative genera of the Caligidae family, Lepeophtheirus and Caligus (C), cause considerable losses in salmonid aquaculture. Examples of species in the genus Lepeophtheirus include Lepeophtheirus salmonis oncorhynchi and Lepeophtheirus salmonis Lernanthropus koyeri, while examples of species in the genus Caligus include Caligus clemensi, Caligus curtus, Caligus dussumieri, Caligus elongatus, Caligus longicaudatus, Caligus rogercresseyi, Caligus stromii, and Caligus minimus.

[0327] L. salmonis is found only in the Northern Hemisphere. C. rogercresseyi is the most important sea louse species in Chile, affecting the salmon industry.

[0328] One representative family of Lernanthropidae is of concern, mainly in Mediterranean fish farming: species within the genus Lernanthropus include, for example, Lernanthropus kroyeri, Lernanthropus callinomymicola, Lernanthropus indefinitus, Lernanthropus cynoscicola, and Lernanthropus gisleri.

[0329] In one embodiment, the compound is used to control sea louse infestation, which is at least one of Lepeophtheirus salmonis, Caligus clemensi, Caligus curtus, Caligus dussumieri, Caligus elongatus, Caligus longicaudatus, Caligus rogercresseyi, or Caligus stromii, Caligus minimus, or Lernanthropus kroyeri.

[0330] In another embodiment, the compound is used to control parasitism by fish-parasitic crustaceans, which are at least one of Lepeophtheirus kroyeri and Caligus minimus.

[0331] The compound of formula (I) was found to be effective in controlling various stages of fish-parasitic crustaceans, particularly sea lice.

[0332] In one embodiment, the compound of formula (I) is used to control fish-parasitic crustaceans, particularly copepods, sea louse parasitism by pre-adult or adult sea lice, or mixed parasitism at various stages.

[0333] Fish-parasitic crustaceans, such as the Caligid sea louse, possess both free-swimming (plankton-like) and parasitic life stages, all of which are separated by molting.

[0334] The egg hatches into nauplius I, which molts into a second nauplius stage; both nauplius stages are non-feeding, relying on yolk reserves for energy, and are adapted to swimming. The next life cycle stage, the copepodid stage, is the infection stage, and the organism searches for a suitable host, possibly through chemosensory and mechanosensory cues.

[0335] Infection with *Caligid* sea slugs occurs during the copepod plankton stage (larva). The copepods attach to a suitable host supply during the period before molting to the *Caligid* I stage. Sea lice continue to grow through molting, reaching up to four *Caligid* stages. A characteristic feature of all *Caligid* stages is their physical attachment to the host via structures called anterior filaments. Differences in the timing, production method, and physical structure of the anterior filaments are observed among different species of sea lice.

[0336] Except for a short period during molting, pre-adult and adult stages are mobile on fish and, in some cases, can move between host fish. Adult females are larger and occupy a relatively flat body surface along the posterior ventral and dorsal midline, as well as the head region.

[0337] The nauplius and copepodid stages, before the sea locates the host, are non-feeding and survive on endogenous food stores. Once attached to a host, the copepodid stage begins feeding and develops into the first chalimus stage. The copepodid and chalimus stages have well-developed gastrointestinal tracts and feed on host mucus and tissue within the area of ​​attachment (attachment stage). Pre-adult and adult sea lice, especially fertilized egg females, are aggressive feeders and, in some cases, feed on blood in addition to tissue and mucus.

[0338] As used herein, “juvenile sea louse” refers to the stage before an individual matures into a pre-adult and adult stage, and includes the copepodid and calimid parasitic stages of sea lice.

[0339] As used herein, the term “fixed stage” means the juvenile stage and the “mobile” stage—the pre-adult stage and the adult stage.

[0340] In one embodiment, existing parasitic infestations of fish populations are treated at mobile stages, such as the adult sea louse stage and / or pre-adult stage. This is particularly important because these parasitic stages cause the most serious damage when feeding on fish.

[0341] Fish parasitism means that at least one member of the parasitic stage is visible on the surface of the fish. In special cases, an automated sea louse counting method can be used to detect sea louse infestation and its spread by counting the parasitic organisms.

[0342] In an alternative, preferred embodiment, existing infestations of juvenile sea lice (sessile stage) on fish populations are treated, as determined by sea louse counting methods. Control of such juvenile sea louse infestations is desirable because controlling the juvenile stage provides a long-term effect in protecting fish from pre-adult or adult stage infestations of sea lice on fish, particularly from adult female sea lice.

[0343] In another embodiment, existing parasitic infestations of fish populations by juvenile sea lice (sessile stage) and adult sea lice (mobile stage) are treated.

[0344] In one embodiment, a single dose of the compound of formula (I) protects a fish population from reinfestation by parasites, particularly sea lice, over a period of four weeks, such that the treatment interval is four weeks (i.e., the time between administrations is four weeks).

[0345] In one embodiment, the time between administrations is 2 to 8 weeks, preferably 3 to 6 weeks, and more preferably about 4 weeks. Reparasitism means that an individual has been parasitized by a particular parasite, and subsequently, parasitism by other parasites from the environment or contact with a parasitized fish or equipment has been established on the same animal.

[0346] In other embodiments, the parasites are of the genus Argulus, and Argulus (sea louse), Lernaea, and Ergasilus belong to the crustacea and are considered important ectoparasites of fish. The parasitic copepods Argulus and Lernaea attach to the body of a fish, their bodies embedded in scale pockets, and their paired egg sacs protruding freely. Argulus spp. attaches to the fish body particularly by suckers and hooks, but can also swim freely in the water. Pest control As used herein, the term “control” means reducing the number of parasites, especially ichthyopora crustaceans, especially sea lice; eliminating parasites, especially ichthyopora crustaceans, especially sea lice; and / or preventing further parasitism, especially by ichthyopora crustaceans, especially sea lice, in their preadult and adult stages.

[0347] "Treatment" refers to preventive or responsive measures such as controlling, eliminating, protecting, and / or preventing infestations or conditions of fish parasites (e.g., sea lice) in fish or fish populations. This term includes reducing the average number of parasites (e.g., sea lice) infesting each fish in a fish population, or preventing an increase in the average number of parasites currently infesting each fish in a fish population; that is, treating existing parasitic infestations, or, in addition to or instead of doing so, preventing the development of symptoms associated with parasitic infestations or infections, such as reducing the severity of any infestation-related disorders, conditions, or symptoms. This term also includes references to "control" (e.g., killing, repelling, driving out, incapacitating, suppressing, eliminating, mitigating, minimizing, and eradicating).

[0348] In most countries, salmon producers are required to regularly report data on sea louse levels and treatment. Regional regulations, for example, require weekly samples of at least five fish per netpen from a minimum of six netpens when the water temperature exceeds 5°C. In all cases, fish-level sea louse counts are reported for different parasite life stages: Kalymus, adult males and pre-adult males and females (PAAMs), and adult females (AFs; both fertilized and unfertilized eggs). In Norway, fish populations are treated if an average of more than 0.5 adult female sea lice per fish is detected in aquaculture facilities. Aquaculture facilities are entities that raise salmon, sometimes called fish farms. In Scotland, the requirement is that if an average of three adult female sea lice per fish are found during a week's count, this must be reported.

[0349] In a preferred embodiment, the compound of formula (I) is used to control sea louse infestation when the infestation rate in a fish population in an aquaculture facility is an average of 0.5 to 3 adult female sea lice per fish. Effective dose and route of administration As used herein, the term “effective dose” refers to the amount or dosage of the compound of formula (I) or a salt thereof that provides the desired effect when administered to a fish or a population of fish, either once or multiple times.

[0350] When determining the effective dose, many factors are considered, but are not limited to: the fish species; the degree of parasitic infestation; the response of the fish population; the mode of administration; the bioavailability characteristics of the administered preparation; the selected dose regimen; the use of combination drugs; and other relevant circumstances.

[0351] As used herein, “therapeutic dose” means, unless otherwise specified, an amount that (i) treats a particular parasitic infestation, (ii) reduces, improves or eliminates one or more symptoms of a particular parasitic infestation, or (iii) prevents or delays the onset of one or more symptoms of a particular parasitic infestation as described herein.

[0352] Compounds of formula (I) or salts thereof can be administered to fish by any route that produces the desired effect, including, but not limited to, oral administration, parenteral administration by intraperitoneal or intramuscular injection, or topical administration, for example, in the form of a bath.

[0353] Therefore, in one embodiment, the compound is applied to fish by oral administration, topical administration such as bath treatment, etc. (bath treatment includes immersion of fish in water containing a therapeutically effective amount of the compound (medicinal water), or injection into fish by intraperitoneal or intramuscular injection.

[0354] In one embodiment, the fish are treated, for example, by oral administration via feed. Alternatively, treatment may be performed locally by bath treatment, for example, by a "medicinal bath" in which the fish are placed and maintained for a certain period (several minutes to several hours) when they are moved from one rearing pond to another.

[0355] In certain cases, the treatment may also be administered parenterally, for example by injection such as intraperitoneal or intramuscular injection. It is also possible to treat a fish biotope, such as a net cage, an entire pond, a tank, or a tank in which fish are kept, either temporarily or continuously.

[0356] One aspect of the present invention is a composition comprising one or more compounds of formula (I) and a veterinarily acceptable formulation adjuvant for use in controlling parasitic infections in fish populations.

[0357] As used herein, “veterinary acceptable” means, unless otherwise specified, that an ingredient must be chemically and / or toxicologically compatible with a composition, a composition, and / or other ingredients, including the fish treated therewith. The term “pharmaceutically acceptable” has the same meaning as “veterinary acceptable” as listed herein.

[0358] The compositions include those suitable for the aforementioned routes of administration. The compositions can be conveniently provided in unit dosage forms and can be prepared by any method well known in the field of veterinary medicine. Generally, the compositions are prepared by homogeneously and closely associating the active ingredient with a liquid carrier, a finely divided solid carrier, or both, and then shaping the product as needed.

[0359] The compound is administered in a composition tailored to its intended use. Compositions for oral administration may be, for example, powders, granules, solutions, emulsified concentrates, or suspension concentrates that are uniformly mixed with feed as a feed additive, or powders, granules, solutions, emulsified concentrates, or suspension concentrates administered in pill form, the outer shell of which may consist, for example, a fish feed composition that completely covers the active compound.

[0360] Compositions for bath application or treatment of biotopes may be in the form of powders, granules, solutions, emulsions or suspensions, tablets, or the active compound itself.

[0361] The compositions are typically prepared by mixing, granulating, and / or compressing the active compound with a solid or liquid carrier, and optionally adding further auxiliary agents, such as emulsifiers or dispersants, solubilizers, colorants, antioxidants, and / or preservatives.

[0362] In practice, for example, it is also possible to use application forms in which the active compound is contained in a readily water-soluble matrix of the film, or in a film that diffuses over the duration of application.

[0363] The diluted compositions of the present invention are prepared by contacting the compound of formula (I) with liquid and / or solid compositional aids by stepwise mixing and / or grinding, so as to achieve optimal development of the antiparasitic activity of the composition suitable for the application.

[0364] Bath application of the composition of the present invention to the parasites to be controlled can be carried out, for example, by placing the composition in a cage in the form of a solution, emulsion, suspension, powder, or tablet, where it is rapidly dissolved and dispersed by the movement of fish and the flow of water. Bathing treatment The compound of formula (I) can be administered to fish by bath treatment, for example, by placing the fish in a "medicinal bath" and keeping them there for a certain period of time (from a few minutes to several hours) when, for example, they are moved from one net pen or aquarium to another.

[0365] Therefore, in one embodiment, an effective amount of at least one compound of formula (I) is administered to the fish by topical administration, preferably by immersing the fish in water containing a therapeutically effective amount of one or more compounds of formula (I). For use as a bath treatment, a compound of formula (I) or a composition containing at least one compound of formula (I) can be dissolved or suspended in water containing fish and / or parasites to form medicinal water.

[0366] Another aspect of the present invention is a composition comprising at least one compound of formula (I) for dilution, to be used as a bath immersion treatment for controlling parasitic infections of fish from sea lice.

[0367] In one embodiment, such a composition comprises one or more compounds of formula (I) in the form of a stock solution for dilution in a certain volume of water to form a medicinal water for use as a bath immersion treatment, and a veterinarily acceptable formulation aid. Preferably, the effective amount in the medicinal water is about 2 ppb to about 500 ppb.

[0368] In one embodiment, a concentrated solution of the compound in a liquid carrier containing a stock solution, a solvent, and a solubilizer is used, which can be diluted with a large amount of water.

[0369] In yet another aspect of the present invention, the composition is a stock solution of the compound of formula (I) to be diluted in a certain amount of water for use as a bath immersion treatment to control parasitic sea lice infestation of fish.

[0370] In yet another aspect of the present invention, a stock solution of the compound of formula (I) comprises a solvent and optionally a solubilizer.

[0371] The solvent may be a non-aqueous polar solvent such as methanol, ethanol, benzyl alcohol, isopropanol, acetone, methylene chloride, butyl diglycol, N-methyl-2-pyrrolidone, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, polyoxyethylated ether, propylene glycol, ethylene glycol, and mixtures thereof. In yet another aspect of the present invention, the non-aqueous polar solvent is selected from ethanol, benzyl alcohol, isopropanol, acetone, butyl diglycol, N-methyl-2-pyrrolidone, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, and mixtures thereof. In yet another aspect of the present invention, the non-aqueous polar solvent is selected from benzyl alcohol, butyl diglycol, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and mixtures thereof.

[0372] The composition may further contain solubilizers such as polyoxyethylene castor oil derivatives, polysorbates, caprylic / capric acid glycerides, poloxamers, polyoxyethylene alkyl ethers, polyoxylglycerides, sorbitan fatty acid esters, polyoxyethylated 12-hydroxystearic acid, propylene glycol esters, polyglycerol esters, polyvinylpyrrolidone, cyclodextrin, polyethylene glycol, glyceryl stearate, glyceryl caprylate, glyceryl monooleate, glyceryl caprate, alcohol ethoxylates, and mixtures thereof.

[0373] Using the compound of formula (I), immersion baths containing different concentrations of the compound of formula (I) can be prepared to achieve the required dosage concentration. The stock solution may be diluted at least once before mixing with water, or it may be poured directly into a certain amount of water for the treatment of fish.

[0374] The concentration of the compound during application to fish depends on the method and duration of treatment, as well as the age and condition of the fish being treated. Typical immersion times range from about 15 minutes to about 4 hours, preferably about 15 minutes to 2 hours, and more preferably about 30 minutes to about 1 hour.

[0375] The compound of formula (I) can be used in a bath at therapeutically effective doses or concentrations of approximately 2 ppb to 500 ppb; or approximately 5 ppb to 500 ppb; or approximately 5 ppb to 250 ppb; or approximately 5 ppb to 200 ppb; or approximately 5 ppb to 100 ppb; or approximately 5 ppb to 90 ppb; or approximately 5 ppb to 80 ppb; or approximately 5 ppb to 60 ppb; or approximately 5 ppb to 50 ppb; or approximately 5 ppb to 40 ppb; or approximately 5 ppb to 25 ppb, based on the total volume of water.

[0376] All effective concentrations are measured in ppb in the volume of water (fresh salt, brackish water) used to treat fish against copepod crustacean species, particularly sea lice. The concentration is achieved by adding a certain volume of concentrated stock solution of the compound of formula (I), for example, 50 mg / ml or 100 mg / ml, to the enclosure containing the fish. Those skilled in the art can determine how much of the compound stock solution to add from knowledge of the volume of the enclosure containing the fish and the concentration of the stock solution. Medicated feed, premix The active compounds in these compositions are used in their pure form, for example, as solid active compounds of a specific particle size, or preferably together with at least one adjuvant conventionally used in compositional art, such as an extender, typically a solvent or solid support, or a surface active compound (surfactant).

[0377] The compounds can be added to feed by conventional methods, either by simply mixing them as pure compounds such as powders, or by mixing them with edible, non-toxic, veterinarily acceptable excipients in the form of veterinary compositions, and may be included as premixes in the form of solutions or suspensions, granules, or pellets.

[0378] In one embodiment of the present invention, the compound of formula (I) or a salt thereof is administered into medicinal fish feed.

[0379] Therefore, another embodiment is a composition comprising one or more compounds of formula (I) and a veterinarily acceptable formulation adjuvant for oral administration via feed.

[0380] Certain compositions are "premixes" (in tons) that facilitate the uniform mixing of relatively small amounts of active ingredients in / on fish feed.

[0381] Therefore, one aspect of the present invention is a premix comprising a nutrient, a formulation adjuvant, and at least one compound of formula (I).

[0382] In one embodiment, the nutrient feed for fish is in the form of pellets mixed with or coated with a composition comprising one or more compounds of formula (I) as defined in claim 1. Such a composition may contain compounds of formula (I) as a solution or in particulate form.

[0383] Another aspect of the present invention is a medicated fish feed comprising a composition or premix and a nutrient feed for fish. Such feed is prepared by a commercial feed factory according to a veterinarian's instructions or based on a label and shipped to a fish farm. Alternatively, such medicated feed is prepared at a fish farm.

[0384] In one embodiment, medicated fish feed is administered daily for 3 to 14 days.

[0385] In one embodiment of the present invention, the compound of formula (I) or a salt thereof is administered orally at a daily dose of 1 to 10 mg / kg of fish biomass, preferably 3 to 7 mg / kg of fish biomass, and most preferably about 5 mg / kg of fish biomass.

[0386] In one embodiment, the total treatment period during which the compound of formula (I) or a salt thereof is administered is 3 to 14 days (about 2 weeks), 3 to 7 days in one embodiment, 5 to 14 days in another embodiment, 5 to 10 days (about 1.5 weeks) in another embodiment, preferably 7 days. During the entire treatment period, the compound of formula (I) or a salt thereof may be administered, for example, daily or every other day. Preferably, it is administered daily. In a preferred embodiment, administration is daily for 7 days.

[0387] In a preferred embodiment, the compound of formula (I) or a salt thereof is administered orally at a daily dose of 1 to 10 mg / kg of fish biomass for 3 to 14 days (about 2 weeks). In another preferred embodiment, the compound of formula (I) or a salt thereof is administered orally at a daily dose of 3 to 7 mg / kg of fish biomass for 5 to 10 days. In a more preferred embodiment, the compound of formula (I) or a salt thereof is administered orally at a daily dose of about 5 mg / kg of fish biomass for 7 days.

[0388] It will be understood that the amount of compound administered to fish to achieve the desired effect may vary due to the compound's desirable non-toxic properties. In one embodiment, the compound is administered orally at approximately 0.005 to 5000 mg / kg, particularly 0.01 to 500 mg / kg (i.e., mg of compound per kg of fish body weight per day). Furthermore, the compound can be administered at relatively high doses, such as greater than 0.01 mg / kg (i.e., greater than), greater than 0.1 mg / kg, greater than 1 mg / kg, greater than 10 mg / kg, or even greater than 100 mg / kg. The duration of administration may range from a few hours or a few days to several years.

[0389] Therefore, oral administration involves administering a medicinal fish feed containing the compound of formula (I) to a fish population. The fish feed is typically in the form of granules or pellets. Common components of the fish feed granules or pellets include fish meal, fish oil, vegetable proteins, sugars, and polysaccharides (including mannan, glucan, and alginate). Excipients such as pigments, vitamins, minerals, and binders may also be included.

[0390] The compound of formula (I) or a salt thereof may be incorporated into the feed before pelletization, or the compound of formula (I) or a salt thereof may be coated onto granules or pellets, either on its own or in the form of a premix. In addition to the active compound, the premix may contain one or more veterinarily acceptable excipients, such as starch, fumed silica, microcrystalline cellulose, lactose, and preservatives.

[0391] The compound may be incorporated into the feed mixture before pelletization. However, it is preferable to coat the pellets or granules with the compound of formula (I). For example, commercially available fish pellets or granules may be coated with the compound of formula (I) using a solution in a veterinarily acceptable solvent, suspended on a carrier, or coated with a premix containing the compound of formula (I) and one or more veterinarily acceptable excipients, such as starch, fumed silica (Aerosil®), microcrystalline cellulose, or lactose. In addition, typical preservatives may be present.

[0392] The concentration of the compound of formula (I) in the premix can be selected within a wide range; for example, based on the total weight of the premix in each case, concentrations of the compound of formula (I) at concentrations of 0.001 to 90% w / w, preferably 1 to 50% w / w, more preferably 5 to 15% w / w, and according to further embodiments, 0.001 to 10% w / w, preferably 0.05 to 5% w / w, and particularly 0.15 to 2.5% w / w have proven useful.

[0393] Feed pellets may be coated with a premix by a dry top coating method. For this purpose, the premix is ​​added to the pellets, and the resulting mixture is stirred / mixed to uniformly distribute the compound of formula (I) onto the pellets. According to an alternative top coating method with additional oil treatment, fish oil or vegetable oil is added to the product of the dry top coating method described above, while continuing to mix until the pellets are completely coated. According to yet another embodiment called a vacuum coating method, the premix is ​​first dissolved / suspended in fish oil or vegetable oil before being sprayed onto the pellets under vacuum. A solution is preferred.

[0394] After the active ingredient is added to the fish feed, the pellets or granules contain, for example, about 0.0005 to about 5% (w / w), preferably about 0.001 to about 2.5% (w / w), and especially about 0.0025 to about 1.25% (w / w), of the compound of formula (I), based on the total weight of the fish feed.

[0395] In one embodiment of the present invention, the amount of compound (I) or its salt present in the fish feed premix composition is, in all cases, about 5 to about 20% (w / w), preferably about 10 to about 15% (w / w), and most preferably about 12.5% ​​(w / w), based on the total weight of the premix. combination The compounds and compositions can also be used in combination with one or more other physiologically active agents.

[0396] Therefore, in one embodiment, the compound is co-administered with further physiological agents. Such combinations are selected based on the condition being treated, the cross-reactivity of the components, and the pharmacological properties of the combination. For example, multi-functional agents such as polyvalent vaccines are preferred for treating fish, so the composition may be administered with antigens targeting bacterial or viral diseases. In one embodiment, the compound of formula (I) is co-administered with one or more antigens, and optionally, the compound and antigens are administered together with an adjuvant.

[0397] These compounds and compositions may be administered together with, or in the same process as, the treatment with the compounds and compositions described herein. Co-administration means that the individual components of the combination may be administered sequentially or simultaneously in separate or combined veterinary compositions.

[0398] Administration of the compound of formula (I) alone generally provides long-term control of sea louse infestations, but such control may be further improved in certain situations by using the compound of formula (I) in combination with another bioactive agent.

[0399] Such physiologically active agents include other antiparasitic agents, particularly sea louse control agents; vaccine components containing antibiotics or immunostimulants; or feed components containing immunomodulators.

[0400] Such combination treatments may be necessary if the fish are already infected with mature parasites before treatment with the compound of formula (I), or if rapid clearance of the parasites is desired.

[0401] Therefore, in one embodiment, the compound of formula (I) is co-administered with at least one further physiologically active agent.

[0402] Suitable antiparasitic agents include, for example, hydrogen peroxide; formaldehyde; organophosphates such as trichlorfon, malathion, dichlorvos, or azamethiphos; macrocyclic lactones such as ivermectin, emamectin benzoate, or moxidectin; pyrethroids such as cypermethrin or deltamethrin; neonicotinoids such as imidacloprid, nitenpyram, thiamethoxam, or thiacloprid; spinosins such as spinosad; IGRs such as epophenonane, triprene, methoprene, or lufenuron; or carbamates such as phenoxycarb.

[0403] When the compound of formula (I) is used in combination with another compound that is active in controlling sea lice, the combination partner is preferably an organophosphate, pyrethroid, such as cypermethrin or deltamethrin, macrocyclic lactone, such as emamectin benzoate; hydrogen peroxide; or neonicotinoid such as imidacloprid or thiacloprid.

[0404] In other embodiments, the combination partner is one or more isoxazoline compounds known in the art. Isoxazoline activators are highly effective against a variety of ectoparasites, and combinations with compounds of formula (I) will extend the range of effectiveness against these parasites. Particularly useful isoxazoline activators that can be combined with the compound include afoxolaner (containing substantially pure active enantiomers), sarolaner, fluralaner (containing substantially pure active enantiomers), and rotilaner.

[0405] These activators are described in U.S. Patent No. 7,964,204, U.S. Patent Publication No. 2010 / 0254960Al, U.S. Patent Publication No. 2011 / 0159107, U.S. Patent Publication No. 2012 / 0309620, U.S. Patent Publication No. 2012 / 0030841, U.S. Patent Publication No. 2010 / 0069247, International Publication No. 2007 / 125984, International Publication No. 2012 / 086462, U.S. Patent No. 8,318,757, U.S. Patent No. 8,466,115, U.S. Patent No. 8,618,126, and the same. U.S. Patent Publication No. 8,822,466, No. 8,383,659, No. 8,853,186, No. 9,221,835, U.S. Patent Publication No. 2011 / 0144349, U.S. Patent No. 8,053,452; U.S. Patent Publication No. 2010 / 0137612, U.S. Patent No. 8,410,153, U.S. Patent Publication No. 2011 / 152081, International Publication Brochure No. 2012 / 089623, International Publication Brochure No. 2012 / 089622, U.S. Patent No. 8,119,671; U.S. Patent No. 7,947,715;International Publication No. 2102 / 120135, International Publication No. 2012 / 107533, International Publication No. 2011 / 157748, U.S. Patent Application Publication No. 2011 / 0245274, U.S. Patent Application Publication No. 2011 / 0245239, U.S. Patent Application Publication No. 2012 / 0232026, U.S. Patent Application Publication No. 2012 / 0077765, U.S. Patent Application Publication No. 2012 / 0035122, U.S. Patent Application Publication No. 2011 / 0251247 Book, International Publication No. 2011 / 154433 pamphlet, International Publication No. 2011 / 154434 pamphlet, US Patent Application Publication No. 2012 / 0238517 specification, US Patent Application Publication No. 2011 / 0166193 specification, International Publication No. 2011 / 104088 pamphlet, International Publication No. 2011 / 104087 pamphlet, International Publication No. 2011 / 104089 pamphlet, US Patent Application Publication No. 2012 / 015946 specification, US Patent Application Publication No. 2009 / 0143410 specification, country U.S. Patent Publication No. 2007 / 123855A2, U.S. Patent Application Publication No. 2011 / 0118212, U.S. Patent No. 7,951,828 and U.S. Patent Application Publication No. 7,662,972, U.S. Patent Application Publication No. 2010 / 0137372Al, U.S. Patent Application Publication No. 2010 / 0179194A2, U.S. Patent Application Publication No. 2011 / 0086886A2, U.S. Patent Application Publication No. 2011 / 0059988Al, U.S. Patent Application Publication No. 2010 / 017919 This is described in the 5Al specification, U.S. Patent Application Publication No. 2015 / 0126523, International Publication No. 2010 / 003923, International Publication No. 2010 / 003877, International Publication No. 2010 / 072602, International Publication No. 2014 / 134236, International Publication No. 2017 / 147352, U.S. Patent No. 7,897,630, and U.S. Patent No. 7,951,828, all of which are incorporated herein by reference in their entirety.

[0406] Another combination partner is 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-yl]pyrazole-4-yl]benzamide (CAS RN 1621436). This compound is known as tigolane.

[0407] A suitable combination treatment of the compound of formula (I) and another lice control agent can be carried out, for example, by first treating fish, especially salmon, with the compound of formula (I) according to the feed method and regime described above, and then, for example, 3 months, preferably 5 months, more preferably 6 months, and especially 9 months after the completion of the feed treatment of the compound of formula (I); the second treatment may be by topical administration, such as a bath treatment, or oral administration, such as a feed treatment, or preferably by injecting the additional lice control agent into the fish. According to a preferred embodiment of this combination treatment, the feed treatment with the compound of formula (I) is carried out at the end of the freshwater phase of salmon evolution or at the beginning of its saltwater phase.

[0408] Further combined treatments include first treating fish, particularly salmon, with an additional lice control agent, and then, for example, 1 hour to 2 months later, preferably 1 hour to 1 month later, or particularly 1 week to 1 month later, in a feed treatment of the compound of formula (I) according to the present invention. According to a preferred embodiment of this combined treatment, the treatment with the additional lice control agent is a bath treatment, feed treatment, or injectable treatment performed at the start of the seawater phase, for example, 1 hour to 3 months, preferably 6 hours to 2 months later.

[0409] According to further embodiments of the present invention, infusion treatment with a compound of formula (I) is combined with vaccination of fish against typical bacterial or viral infections. Typical bacterial diseases treated by vaccination include, for example, vibriosis, furuncuosis, wound disease, atypical Aeromonas salmonicida, piscilrickettsia, or ERM / Yersiniasis. Examples of viral diseases treated include pancreatic disease / PDV, infectious pancreatic necrosis / IPNV, or infectious salmon anemia / ISAV. The vaccine is generally applied by bath or infusion treatment, or preferably by injection. Vaccination may be performed immediately before, during, or after the infusion treatment of fish.

[0410] In one embodiment of this combination treatment, the first treatment is a bath treatment with the compound of formula (I), followed by a feed treatment with hexaflumurone or lufenuron, the compound of formula (I), or emamectin, which can provide sustained protection against sea lice. In another embodiment, this combination treatment is a feed treatment with hexaflumurone or lufenuron, the compound of formula (I), or emamectin, which can provide sustained protection against sea lice, followed by a bath treatment with the compound of formula (I).

[0411] In another embodiment, the compound of formula (I) is administered in combination with a vitamin that improves the health of the animal.

[0412] There is abundant evidence worldwide of resistance in sea lice to chemotherapeutic agents.

[0413] Surprisingly, the compound of formula (I) was found to be effective in controlling louse populations that have been identified as resistant to commercially available louse chemotherapeutic agents of the class of organophosphates, macrocyclic lactones, particularly avermectin, and pyrethroids, as shown in the examples.

[0414] As used herein, "resistance" refers to a decrease in the potency of a compound compared to naive parasites, particularly sea lice. The first occurrence of this phenomenon was reported in Norway, where resistance to organophosphates, especially azamethiphos, increased to the point of complete loss of effectiveness by the mid-1990s. Subsequently, failures of pyrethroid-related treatments were reported in Norway, Scotland, and Ireland. Subsequent analyses, based on bioassays, confirmed decreased susceptibility to deltamethrin and cypermethrin. Recent bioassay-based studies have confirmed the low susceptibility of C. rogercresseyi to pyrethroids. Therefore, it is of particular importance to make available new and effective compounds that can effectively control such resistant parasite populations.

[0415] Therefore, in one embodiment, infestation of sea lice by parasites resistant to macrocyclic lactones, organophosphates, and / or pyrethroids is controlled, and it has been found that sea lice are resistant to macrocyclic lactones, organophosphates, and / or pyrethroid antiparasitic agents.

[0416] In one embodiment, such a sea louse population is resistant to emamectin, deltamethrin, or one or more organophosphates. kit Another aspect of the present invention is a kit comprising a compound of formula (I) or the above-mentioned composition containing such a compound, and instructions for administering the composition to fish.

[0417] In one embodiment, the kit includes a premix as described above, as well as instructions for preparing a medicated fish feed for controlling sea louse infestation and / or instructions for administering the medicated fish feed to a fish population, as described in more detail above.

[0418] In another embodiment, the kit includes a stock solution as described above, as well as instructions for preparing medicinal water for bath treatment, and / or instructions for immersing fish to control sea louse infestation.

[0419] The following table shows the compounds of the present invention.

[0420] [ka]

[0421] [Table 1]

[0422] [Table 2]

[0423] [Table 3]

[0424] [Table 4] [Brief explanation of the drawing]

[0425] [Figure 1-1] Figure 1: Figure 1 shows the structure of the compound. [Figure 1-2] (As stated above.) [Figure 1-3] (As stated above.) [Figure 1-4] (As stated above.) [Figure 1-5] (As stated above.) [Figure 1-6] (As stated above.) [Figure 1-7] (As stated above.) [Figure 1-8] (As stated above.) [Figure 1-9] (As stated above.) [Figure 1-10] (As stated above.) [Figure 1-11] (As stated above.) [Figure 1-12] (As stated above.) [Figure 1-13] (As stated above.) [Figure 1-14] (As stated above.) [Figure 1-15] (As stated above.) [Figure 1-16] (As stated above.) [Figure 1-17] (As stated above.) [Figure 1-18] (As stated above.) [Figure 1-19] (As stated above.) [Figure 1-20] (As stated above.) [Figure 1-21] (As stated above.) [Figure 1-22] (As stated above.) [Figure 1-23] (As stated above.) [Figure 1-24] (As stated above.) [Figure 1-25] (As stated above.) [Figure 1-26] (As stated above.) For example, the compounds were synthesized according to International Publication No. 2018071327, International Publication No. 2016168058, and International Publication No. 2016168056, and the following compounds were prepared according to the following synthesis scheme. Synthesis scheme for 1633:

[0426] [ka]

[0427] Process-1: Synthesis of 2-fluoro-5-nitrobenzoyl chloride (1):

[0428] [ka]

[0429] Experimental procedure: To a stirred solution of 2-fluoro-5-nitrobenzoic acid (SM-1) (4 g, 21.62 mmol) in DCM (60 ml), oxalyl chloride (2.5 ml, 32.43 mmol) was added at 0°C and the mixture was stirred for 5 minutes. A catalytic amount of DMF (0.1 ml) was added, and the reaction mixture was stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC (50% ethyl acetate in petroleum ether). After the completion of the reaction, the reaction mixture was completely removed under vacuum to obtain 2,fluoro-5-nitrobenzoyl chloride (1) (4.1 g, crude compound) as a light brown semi-solid. Process-2: Synthesis of N-(1-ethynylcyclopropyl)-2-fluoro-5-nitrobenzamide (2):

[0430] [ka]

[0431] Experimental procedure: A stirred solution of 1-ethynylcyclopropan-1-amine (SM-2) (1.4 g, 12.35 mmol) in THF (21 ml) was cooled to 0°C, DIPEA (5.3 ml, 30.88 mmol) was added, and the mixture was stirred for 10 minutes. To this, 2-fluoro-5-nitrobenzoyl chloride (1) (2.1 g, 10.29 mmol) was added in THF (20 ml), and the reaction mixture was stirred at room temperature for 6 hours. The progress of the reaction was monitored by TLC (50% ethyl acetate in petroleum ether) (Rf = 0.7). After the completion of the reaction, H2O (20 ml) was added to the reaction mixture, extracted with EtOAC (2 × 30 ml), dried on Na2SO4, and concentrated under reduced pressure to obtain N-(1-ethynylcyclopropyl)-2-fluoro-5-nitrobenzamide (2) (2.8 g, crude) as a brown solid. ESIMS m / z 249.19([M+H] + ). Process-3: Synthesis of 5-amino-N-(1-ethynylcyclopropyl)-2-fluorobenzamide (3)

[0432] [ka]

[0433] Experimental procedure: A stirring solution of N-(1-ethynylcyclopropyl)-2-fluoro-5-nitrobenzamide (2) (6.0 g, 22.53 mmol) was added to MeOH / H2O (85 ml, 1:1 ratio), Fe (3.1 g, 56.45 mmol), and NH4Cl (6.0 g, 112.90 mmol), and the RM was stirred at 80°C for 3 hours. The progress of the reaction was monitored by TLC (50% ethyl acetate in petroleum ether) (0.3 Rf). After the completion of the reaction, the RM was filtered through a Celite bed, washed with MeOH (50 ml), and concentrated. H2O (40 ml) was added, extracted with ELISA (3 × 80 ml), dried on Na2SO4, and concentrated. The crude compound was purified by column chromatography (silica gel 100-200) and eluent gradient through 30% ethyl acetate in petroleum ether. The combined column fractions were concentrated and dried under reduced pressure to obtain 5-amino-N-(1-ethynylcyclopropyl)-2-fluorobenzamide (3) (400 mg, 16%) as a brown solid. ESIMS m / z 219.2 ([M+H] + ). Process-4: Synthesis of 5-((1R,3R)-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide)-N-(1-ethynylcyclopropyl)-2-fluorobenzamide (1633):

[0434] [ka]

[0435] Experimental procedure: A stirred solution of (R,R)-11 (0.4 g, 1.33 mmol) in DCM (20 ml) was cooled to 0°C, and EDC.HCl (0.38 g, 1.99 mmol) and DMAP (0.24 g, 1.99 mmol) were added, and the mixture was stirred for 10 minutes. To this mixture, 5-amino-2,3-difluoro-N-(propa-2-in-1-yl)benzamide (3) (0.28 g, 1.33 mmol) was added, and the mixture was stirred at room temperature for 16 hours. The progress of the reaction was monitored by TLC (50% ethyl acetate in petroleum ether). After the completion of the reaction, H2O (40 ml) was added to the reaction mixture, extracted with DCM (2 × 50 ml), and the combined organic phase was dried over Na2SO4 and concentrated. The crude compound was purified by column chromatography (silica gel 100-200). Eluent: -5-((1R,3R)-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide)-N-(1-ethynylcyclopropyl)-2-fluorobenzamide (1633) (0.38 g, 40%) was obtained as a pale yellow solid using 10% ethyl acetate in a gradient petroleum ether. 1 H NMR(400MHz,DMSO-d6)δ ppm 1.075(s,2H),1.235-1.123(m,2H),3.014(s,1H),3.492-3.471(d,J=8.4Hz,1H),3.620-3.599(d,J= 8.4Hz 1H),7.300-7.254(t,1H),7.547(s,2H),7.622(s,1H),7.749-7.731(m,1H),7.862-7.848(m,1H)8.954(s,1H),10.770(s,1H):ESIMS m / z 499.02([M+H] + ). 1620 synthesis scheme:

[0436] [ka]

[0437] Process-1: Synthesis of 2-chloro-N-(1-ethynylcyclopropyl)-5-nitrobenzamide (2)

[0438] [ka]

[0439] Experimental procedure: A stirred solution of 1-ethynylcyclopropane-1-amine hydrochloride SM-2 (1.06 g, 9.09 mmol, 0.82(d)) in DCM (40 mL) was cooled to 0°C, TEA (3.83 mL, 27.27 mmol) was added, and the mixture was stirred for 10 minutes. To this, 2-chloro-5-nitrobenzoyl chloride (1) (2.0 g, 9.09 mmol) in DCM (10 mL) was added, and the mixture was stirred at room temperature for 6 hours. The progress of the reaction was monitored by TLC (50% ethyl acetate in petroleum ether) (0.7 Rf). After the completion of the reaction, H2O (20 mL) was added to the reaction mixture, extracted with DCM (2 × 30 mL), dried on Na2SO4, and concentrated under reduced pressure to obtain 2-chloro-N-(1-ethynylcyclopropyl)-5-nitrobenzamide (2) (2.1 g, crude) as a brown solid. Process-2: Synthesis of 5-amino-2-chloro-N-(1-ethynylcyclopropyl)benzamide (3)

[0440] [ka]

[0441] Experimental procedure: A stirring solution of 2-chloro-N-(1-ethynylcyclopropyl)-5-nitrobenzamide (2) (2.1 g, 7.94 mmol) was added to EtOH / H2O (63 mL, 4:1 ratio), Fe (2.21 g, 39.71 mmol), and NH4Cl (2.12 g, 39.71 mmol), and the RM was stirred at 80°C for 3 hours. The progress of the reaction was monitored by TLC (ethyl acetate (0.4 Rf)). After the reaction was complete, the RM was filtered through a Celite bed and washed with 10% MeOH / DCM (50 mL). H2O (40 mL) was added, extracted with 10% MeOH / DCM (3 × 80 mL), dried on Na2SO4, and concentrated. The crude compound was purified by column chromatography (silica gel 100-200). Eluent: 15% ethyl acetate in a gradient petroleum ether. The combined column fractions were concentrated and dried under reduced pressure to obtain 5-amino-2-chloro-N-(1-ethynylcyclopropyl)benzamide (3) (0.8 g, 43%) as a light brown solid. Process-3: Synthesis of 2-chloro-5-((1R,3R)-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide)-N-(1-ethynylcyclopropyl)benzamide (1620)

[0442] [ka]

[0443] Experimental procedure: A stirred solution of (R,R)-11 (0.3g, 1.00 mmol) in DCM (20 mL) was cooled to 0°C, and EDC.HCl (0.28g, 1.5 mmol) and DMAP (0.18g, 1.5 mmol) were added, and the mixture was stirred for 10 minutes. 5-amino-2-chloro-N-(1-ethynylcyclopropyl)benzamide (3) (0.23g, 1.00 mmol) was added, and Rm was stirred at room temperature for 6 hours. The reaction progress was monitored by TLC (30% ethyl acetate in petroleum ether) (0.6 Rf). After the reaction was complete, H2O (40 mL) was added to the reaction mixture, extracted with DCM (2 × 50 mL), dried on Na2SO4, and concentrated. The crude compound was purified by column chromatography (silica gel 100-200). Eluent gradient: 27% ethyl acetate in petroleum ether. The combined column fractions were concentrated and dried under reduced pressure to obtain 2-chloro-5-((1R,3R)-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide)-N-(1-ethynylcyclopropyl)benzamide (1620) (0.23 g, 45%) as a grayish-white solid. 1H NMR(400MHz,DMSO-d6)δppm 1.06-1.03(m,2H),1.23-1.15(m,2H),3.031(s,1H),3.50(d,J=8.4Hz,1H),3.621(d,J=8.4Hz,1H),7 .47(d,J=8.4Hz,1H),7.54(s,2H),7.62(s,1H),7.71-7.66(m,2H),9.07(s,1H),10.84(s,1H):ESIMS m / z 515.10([M+H] + ). 1617 synthesis scheme

[0444] [ka]

[0445] Process-1: Synthesis of 2,3-difluoro-5-nitrobenzoyl chloride (1)

[0446] [ka]

[0447] To a stirred solution of 2,3-difluoro-5-nitrobenzoic acid (SM-1) (5 g, 24.63 mmol) in DCM (50 mL), oxalyl chloride (2.67 ml, 29.55 mmol) was added at 0°C and the mixture was stirred for 5 minutes. A catalytic amount of DMF (0.1 ml) was then added, and the reaction mixture was stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC (30% ethyl acetate in petroleum ether). After the reaction was complete, volatile substances were completely removed under vacuum to obtain 2,3-difluoro-5-nitrobenzoyl chloride (1) (5.2 g, crude compound) as a light brown semi-solid. Process-2: Synthesis of N-(1-ethynylcyclopropyl)-2,3-difluoro-5-nitrobenzamide (2)

[0448] [ka]

[0449] Experimental procedure: A stirred solution of 1-ethynylcyclopropane-1-amine SM-2 (1.32 g, 11.28 mmol) in DCM (25 mL) was cooled to 0°C. Triethylamine (TEA) (4.7 mL, 33.85 mmol) was added, and the mixture was stirred for a further 10 minutes. A solution of 2,3-difluoro-5-nitrobenzoyl chloride (1) (2.5 g, 11.28 mmol) in DCM (10 mL) was added, and the mixture was stirred at room temperature (RT) for a further 6 hours. The progress of the reaction was monitored by TLC (50% ethyl acetate in petroleum ether; Rf=0.7). After the completion of the reaction, H2O (20 mL) was added to the reactants, and the mixture was extracted with DCM (2 × 30 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure to obtain N-(1-ethynylcyclopropyl)-2,3-difluoro-5-nitrobenzamide(2) (2.87 g, crude) as a brown solid. ESIMS m / z 267.2([M+H] + ). Process-3: Synthesis of 5-amino-N-(1-ethynylcyclopropyl)-2,3-difluorobenzamide (3)

[0450] [ka]

[0451] Experimental procedure: A stirred solution of N-(1-ethynylcyclopropyl)-2,3-difluoro-5-nitrobenzamide (2) (2.87 g, 10.78 mmol) in EtOH / H2O (57 mL, 4:1 ratio) was reacted with Fe (3.01 g, 53.94 mmol) and NH4Cl (2.88 g, 53.94 mmol) at 80°C for 3 hours. The progress of the reaction was monitored by TLC (50% ethyl acetate in petroleum ether; Rf=0.2). After the reaction was complete, the mixture was filtered through a Celite bed and washed with 10% MeOH / DCM (50 mL). The organic phase was diluted with H2O (40 mL), extracted with 10% MeOH / DCM (3 × 80 mL), and dried over Na2SO4. Purification of the crude compound by column chromatography (silica gel 100-200; eluent: gradient petroleum ether with 18% ethyl acetate) yielded 5-amino-N-(1-ethynylcyclopropyl)-2,3-difluorobenzamide (3) (1.7 g, 67%) as a grayish-white solid. ESIMS m / z 237.2 ([M+H] + ). Process-4: Synthesis of 5-((1R,3R)-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide)-N-(1-ethynylcyclopropyl)-2,3-difluorobenzamide (1617)

[0452] [ka]

[0453] Experimental procedure: A stirred solution of (R,R)-11 (0.350 g, 1.16 mmol) in DCM (20 mL) was cooled to 0°C. EDC.HCl (0.33 g, 1.74 mmol) and DMAP (0.21 g, 1.74 mmol) were added, and the mixture was stirred for 10 minutes. 5-amino-N-(1-ethynylcyclopropyl)-2,3-difluorobenzamide (3) (0.27 g, 1.16 mmol) was added to this mixture, and the mixture was stirred at room temperature for 16 hours. The progress of the reaction was monitored by TLC (30% ethyl acetate in petroleum ether; Rf=0.5). After completion, the reaction product was diluted with H2O (40 mL). The organic phase was extracted with DCM (2 × 50 mL) and dried over Na2SO4. Purification of the crude compound by column chromatography (silica gel 100-200; eluent: gradient petroleum ether with 15% ethyl acetate) yielded 5-((1R,3R)-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide)-N-(1-ethynylcyclopropyl)-2,3-difluorobenzamide (18D) (0.24 g, 40%) as a grayish-white solid. 1H NMR(400MHz,DMSO-d6)δ ppm 1.08(br s,2H),1.18(br s,2H),3.04(s,1H),3.50(d,J=8.4,1H),3.63(d,J=8.4Hz,1H),7.62 -755(m,4H),7.89-7.85(m,1H),9.13(s,1H),10.95(s,1H):ESIMS m / z 517.12([M+H] + ). Chromatography system: Column: Xbridge BEH C 18 Waters, 2.1 x 50 mm, 2.5 μm Oven: 40℃ Eluent: Solvent A: Water / HCO2H (0.05%); Solvent B: Acetonitrile / HCO2H (0.05%) Flow rate: 0.8 ml / min

[0454] [Table 5]

[0455] Execution time: 2.2 minutes + 0.5 minutes equilibrium time

[0456] [Table 6] [Examples]

[0457] Example 1: Contact assay of juvenile sea lice Copepods (juvenile Lepeophtheirus salmonis) were exposed to seawater to which the test compound (dissolved in a DMSO seawater mixture) was added at decreasing concentrations. After approximately 24 hours of continuous exposure, the inhibition of sea lice (percentage of dead and damaged copepods) was evaluated. The vitality of the parasites used was confirmed in a negative (solvent) control group.

[0458] Results: The following compounds showed more than 80% inhibition at a test concentration of 100 nM: (* indicates 100% inhibition) 1514*, 1532*, 1544*, 1545*, 1546*, 1547*, 1549*, 1585*, 1587*, 1591*, 1606*, 1611*, 1616*, 1617*, 1625*, 1627, 1629*, 1631*.

[0459] The following compounds showed more than 80% inhibition at a test concentration of 10 nM: (* indicates 100% inhibition) 1500, 1501, 1502*, 1508*, 1509*, 1510*, 1513*, 1515*, 1526*, 1531*, 1537*, 1539*, 1541*, 1552, 1553*, 1554, 1557*, 1561*, 1566*, 1570, 1573*, 1602*, 1603, 1604*, 1609*, 1612*, 1613*, 1615*, 1618*, 1619*, 1620*, 1621*, 1622, 1626, 1628*, 1630*.

[0460] The following compounds showed more than 80% inhibition at a test concentration of 1 nM: (* indicates 100% inhibition) 1523, 1567*, 1574, 1589, 1590, 1601*, 1614, 1633.

[0461] The following compounds showed more than 80% inhibition at a test concentration of 0.1 nM: (* indicates 100% inhibition) 1584*, 1592, 1594, 1623*, 1624*.

[0462] The following compounds showed more than 80% inhibition at a test concentration of 0.01 nM: (* indicates 100% inhibition) 1536*, 1538*, 1551*, 1558*, 1559*, 1563*, 1565*, 1593*, 1605*, 1608*, 1632. Example 2: Adult sea louse contact assay Mobilized sea lice (i.e., pre-adult and adult stages of Lepeophtheirus salmonis) were exposed to seawater to which the test compound (dissolved in a PEG seawater mixture) was added at decreasing concentrations. Compared to a negative (solvent) control group, sea louse inhibition (percentage of dead and injured sea lice) was evaluated after approximately 1 hour and 24 hours of continuous exposure.

[0463] Results: The following compounds exhibited EC values ​​below 25 nM and above 10 nM. 50 It had: 1514, 1532, 1545, 1546, 1548, 1602, 1603, 1604, 1606, 1612.

[0464] The following compounds have EC values ​​of 10 nM or less and 1 nM or greater. 50 It had: 1508, 1541, 1547, 1585, 1601, 1609, 1615, 1623, 1624, 1626, 1628.

[0465] The following compounds have an EC of 1 nM or less 50 It had: 1584, 1587, 1589, 1590, 1592, 1593, 1594, 1605, 1608, 1613, 1614, 1617, 1618, 1619, 1620, 1621, 1622, 1625, 1630, 1632, 1633. Example 3: Sea louse resistance assay Sea louse resistance assays were performed using mobile sea louse stages (i.e., pre-adult, adult) of several Lepeophtheirus salmonis isolates with known resistance profiles (i.e., fully susceptible or multidrug resistant (resistant to azamethiphos (OP), emamectin benzoate (ML), and deltamethrin (SP))). Sea lice were exposed to seawater to which the test compound (dissolved in PEG300 / seawater mixture) was added at reduced concentrations. Sea louse inhibition (%) of sea lice killed + injured was assessed after approximately 24 and 48 hours of continuous exposure, compared to a negative (solvent) control group.

[0466] Results: Compound 1590 was found to be susceptible to the EC2 isolate. 50 (4.12 ppb after 24 hours and 0.40 ppb after 48 hours) and multidrug-resistant isolates (EC 50 It was equally effective against levels of 3.75 ppb after 24 hours and 0.58 ppb after 48 hours. Salmon-sea louse in vivo efficacy Example 4: Efficacy test using enteral administration: Salmon (Atlantic salmon (Salmo salar)) were orally administered once via tube at a dose of 5 mg / kg body weight per fish (Day 0). The formulation used was DMSO 5% / fish oil 95%. Salmon in the negative control group received only the excipients of the formulation.

[0467] The fish were parasitized with Lepeophtheirus salmonis copepodid twice before treatment (i.e., on approximately day -28 and day -3) and once after treatment (i.e., on day 17).

[0468] On day 7, the fish were examined under sedation, and the number of (pre)adult sea lice in each fish was counted and removed (evaluation of the therapeutic effect against (pre)adult sea lice from infestations up to day 28).

[0469] Around day 28 (end of the animal stage), the fish were euthanized, and the sea lice on each fish were classified (pre-adult or juvenile stage) and counted. The number of pre-adult and juvenile parasites corresponding to each parasitism time was used for efficacy calculations, i.e., evaluation of the therapeutic effectiveness against juvenile sea lice from parasitism on day -3 and the preventive effectiveness from re-infestation on day 17. Efficacy was expressed as the percentage reduction in sea lice in the treated group compared to the control group, using Abbott's formula.

[0470] Results: The following compounds showed more than 80% therapeutic efficacy against (pre)adult sea lice: (* indicates 100% effectiveness) 1541, 1584*, 1585*, 1587, 1590*, 1592*, 1593*, 1594*, 1601*, 1605*, 1606*, 1608*, 1609*, 1617*, 1618*, 1619*, 1620*, 1621*, 1622*, 1623*, 1624*, 1625*, 1626*, 1628*, 1630*, 1632*, 1633*.

[0471] The following compounds showed therapeutic efficacy of over 80% against juvenile sea lice: (* indicates 100% effectiveness) 1541*, 1585*, 1590, 1592*, 1593, 1594*, 1601*, 1605*, 1606*, 1608*, 1609*, 1617*, 1618*, 1619, 1620, 1621, 1623, 1624, 1625*, 1626, 1628*, 1630*, 1632, 1633*.

[0472] The following compounds showed more than 80% prophylactic efficacy in reinfection on day 17. (* indicates 100% effectiveness): 1541*, 1590, 1594*, 1609*, 1617*, 1618*, 1624, 1625*, 1628*, 1630*, 1633. Example 5: Efficacy test using in-feed administration Four test groups of fish were used (one group for evaluating therapeutic efficacy, one for evaluating preventive efficacy, and controls for each of them). Commercial fish feed pellets were coated with the test formulation compound. The formulation used was DMSO 5% / fish oil 95%. Salmon (Atlantic salmon) were orally treated with 1 mg / kg of fish biomass via the coated feed for 7 consecutive days. Negative control salmon were fed only the feed coated with the formulation's excipients.

[0473] The fish in the treatment group were parasitized twice with Lepeophtheirus salmonis copepodid prior to treatment (approximately on day -28 and day -3).

[0474] Around day 8, the fish were examined under sedation, and the number of (pre)adult sea lice in each fish was counted and removed (evaluation of the effectiveness of treatment against (pre)adult sea lice that had infested the fish around day 28).

[0475] Around day 25, the fish were euthanized, and the number of (pre)adult sea lice in each fish was counted (to evaluate the effectiveness of treatment against juvenile sea lice that had infested the fish around day 3).

[0476] Fish in the prevention group were infested with sea lice at two-week intervals at several point points after treatment. Approximately three weeks after each reinfestation, the fish were evaluated for (pre)adult sea lice. At each evaluation, all (pre)adult sea lice were removed from the fish. The number of sea lice on the fish corresponding to each reinfestation point was used to calculate the preventive efficacy. Efficacy was expressed as a percentage reduction in sea lice in the treatment group compared to the control group, using Abbott's formula.

[0477] Results: Compounds 1541, 1590, and 1594 achieved 100% therapeutic efficacy against (pre)adult and juvenile sea lice.

[0478] The prophylactic efficacy against reinfestation after treatment was 100% (D14) and 100% (D28) for compounds 1541 and 1594, respectively.

[0479] The preventive efficacy against reinfestation after treatment was 100% (D14) and 79.2% (D28) for compound 1590. The invention described in the original claims of this application is listed below. [1] The following formula for use in methods for controlling parasitic infestations in fish: [ka] [In the formula, R 1 These are H, F, Cl, Br, I, CN, NH 2 NO 2 、(C 1 ~C 6 ) alkyl, (C 3 ~C 6 )Cycloalkyl, (C 2 ~C 6 ) Alkenil, (C 3 ~C 6 )Cycloalkenyl, (C 2 ~C 6 ) Alkinyl, (C 1 ~C 6 )alkoxy, (C 1 ~C 6 ) Haloalkyl, (C 3 ~C 6 ) Halocycloalkyl, (C 2 ~C 6 ) Haloalkenil, (C 3 ~C 6 ) Halocycloalkenyl, (C 1 ~C 6 ) Haloalkoxy, S(C 1 ~C 6 )alkyl, S(O)(C 1 ~C 6 ) alkyl, S(O) 2 (C 1 ~C 6 ) alkyl, S(C 1 ~C 6 ) Haloalkyl, S(O)(C 1 ~C 6 ) Haloalkyl, S(O) 2 (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 )alkyl-S(O) 2 NH 2 and (C 1~C 6 ) Haloalkyl-S(O) 2 NH 2 Selected from the group consisting of; R 2 These are H, F, Cl, Br, I, CN, NH 2 NO 2 、(C 1 ~C 6 ) alkyl, (C 3 ~C 6 )Cycloalkyl, (C 2 ~C 6 ) Alkenil, (C 3 ~C 6 )Cycloalkenyl, (C 2 ~C 6 ) Alkinyl, (C 1 ~C 6 )alkoxy, (C 1 ~C 6 ) Haloalkyl, (C 3 ~C 6 ) Halocycloalkyl, (C 2 ~C 6 ) Haloalkenil, (C 3 ~C 6 ) Halocycloalkenyl, (C 1 ~C 6 ) Haloalkoxy, S(C 1 ~C 6 )alkyl, S(O)(C 1 ~C 6 ) alkyl, S(O) 2 (C 1 ~C 6 ) alkyl, S(C 1 ~C 6 ) Haloalkyl, S(O)(C 1 ~C 6 ) Haloalkyl, S(O) 2 (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 )alkyl-S(O) 2 NH 2 、(C 1 ~C 6 ) Haloalkyl-S(O) 2 NH 2 and S-(Haro) 5 Selected from the group consisting of; R 3 These are H, F, Cl, Br, I, CN, NH 2 NO 2 、(C 1 ~C 6 ) alkyl, (C 3 ~C 6 )Cycloalkyl, (C 2 ~C 6 ) Alkenil, (C 3 ~C 6 )Cycloalkenyl, (C 2 ~C 6 ) Alkinyl, (C 1 ~C 6 )alkoxy, (C 1 ~C 6 ) Haloalkyl, (C 3 ~C 6 ) Halocycloalkyl, (C 2 ~C 6 ) Haloalkenil, (C 3 ~C 6 ) Halocycloalkenyl, (C 1 ~C 6 ) Haloalkoxy, S(C 1 ~C 6 )alkyl, S(O)(C 1 ~C 6 ) alkyl, S(O) 2 (C 1 ~C 6 ) alkyl, S(C 1 ~C 6 ) Haloalkyl, S(O)(C 1 ~C 6 ) Haloalkyl, S(O) 2 (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 )alkyl-S(O) 2 NH 2 、(C 1 ~C 6 ) Haloalkyl-S(O) 2 NH 2 and S-(Haro) 5 Selected from the group consisting of; R 4 These are H, F, Cl, Br, I, CN, NH 2 NO 2 、(C 1 ~C 6 ) alkyl, (C 3 ~C 6 )Cycloalkyl, (C 2 ~C 6 ) Alkenil, (C 3 ~C 6 )Cycloalkenyl, (C 2 ~C 6 ) Alkinyl, (C 1 ~C 6 )alkoxy, (C 1 ~C 6 ) Haloalkyl, (C 3 ~C 6 ) Halocycloalkyl, (C 2 ~C 6 ) Haloalkenil, (C 3 ~C 6 ) Halocycloalkenyl, (C 1 ~C 6 ) Haloalkoxy, S(C 1 ~C 6 )alkyl, S(O)(C 1 ~C 6 ) alkyl, S(O) 2 (C 1 ~C 6 ) alkyl, S(C 1 ~C 6 ) Haloalkyl, S(O)(C 1 ~C6 ) Haloalkyl, S(O) 2 (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 )alkyl-S(O) 2 NH 2 、(C 1 ~C 6 ) Haloalkyl-S(O) 2 NH 2 and S-(Haro) 5 Selected from the group consisting of; R 5 These are H, F, Cl, Br, I, CN, NH 2 NO 2 、(C 1 ~C 6 ) alkyl, (C 3 ~C 6 )Cycloalkyl, (C 2 ~C 6 ) Alkenil, (C 3 ~C 6 )Cycloalkenyl, (C 2 ~C 6 ) Alkinyl, (C 1 ~C 6 )alkoxy, (C 1 ~C 6 ) Haloalkyl, (C 3 ~C 6 ) Halocycloalkyl, (C 2 ~C 6 ) Haloalkenil, (C 3 ~C 6 ) Halocycloalkenyl, (C 1 ~C 6 ) Haloalkoxy, S(C 1 ~C 6 )alkyl, S(O)(C 1 ~C 6 ) alkyl, S(O) 2 (C 1 ~C 6 ) alkyl, S(C 1 ~C 6 ) Haloalkyl, S(O)(C 1 ~C 6 ) Haloalkyl, S(O) 2 (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 )alkyl-S(O) 2 NH 2 and (C 1 ~C 6 ) Haloalkyl-S(O) 2 NH 2 Selected from the group consisting of; R 6 H and (C 1 ~C 6 Selected from the group consisting of alkyl groups; R 7 It is selected from the group consisting of H, F, Cl, Br, and I; R 8 It is selected from the group consisting of F, Cl, Br, and I; R 9 H and (C 1 ~C 6 Selected from the group consisting of alkyl groups; R 10 H, (C 1 ~C 6 ) alkyl, (C 2 ~C 6 ) Alkenil, (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 ) Alkyl(C 1 ~C 6 )alkoxy, C(=O)(C 1 ~C 6 )alkyl, and (C 1 ~C 6 )alkoxy C (=O) (C 1 ~C 6 Selected from the group consisting of alkyl groups; R 11 These are H, F, Cl, Br, I, CN, NH 2 NO 2 、(C 1 ~C 6 ) alkyl, (C 3 ~C 6 )Cycloalkyl, (C 2 ~C 6 ) Alkenil, (C 3 ~C 6 )Cycloalkenyl, (C 2 ~C 6 ) Alkinyl, (C 1 ~C 6 )alkoxy, (C 1 ~C 6 ) Haloalkyl, (C 3 ~C 6 ) Halocycloalkyl, (C 2 ~C 6 ) Haloalkenil, (C 3 ~C 6 ) Halocycloalkenyl, (C 1 ~C 6 ) Haloalkoxy, S(C 1 ~C 6 )alkyl, S(O)(C 1 ~C 6 ) alkyl, S(O) 2 (C 1 ~C 6 ) alkyl, S(C 1 ~C 6 ) Haloalkyl, S(O)(C 1 ~C 6 ) Haloalkyl, S(O) 2 (C 1 ~C 6 ) Haloalkyl, (C1 ~C 6 )alkyl-S(O) 2 NH 2 and (C 1 ~C 6 ) Haloalkyl-S(O) 2 NH 2 Selected from the group consisting of; R 12 These are H, F, Cl, Br, I, CN, NH 2 NO 2 、(C 1 ~C 6 ) alkyl, (C 3 ~C 6 )Cycloalkyl, (C 2 ~C 6 ) Alkenil, (C 3 ~C 6 )Cycloalkenyl, (C 2 ~C 6 ) Alkinyl, (C 1 ~C 6 )alkoxy, (C 1 ~C 6 ) Haloalkyl, (C 3 ~C 6 ) Halocycloalkyl, (C 2 ~C 6 ) Haloalkenil, (C 3 ~C 6 ) Halocycloalkenyl, (C 1 ~C 6 ) Haloalkoxy, S(C 1 ~C 6 )alkyl, S(O)(C 1 ~C 6 ) alkyl, S(O) 2 (C 1 ~C 6 ) alkyl, S(C 1 ~C 6 ) Haloalkyl, S(O)(C 1 ~C 6 ) Haloalkyl, S(O) 2 (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 )alkyl-S(O) 2 NH 2 and (C 1 ~C 6 ) Haloalkyl-S(O) 2 NH 2 Selected from the group consisting of; R 13 These are H, F, Cl, Br, I, CN, NH 2 NO 2 , CHO, (C 1 ~C 6 ) alkyl, (C 3 ~C 6 )Cycloalkyl, (C 2 ~C 6 ) Alkenil, (C 3 ~C 6 )Cycloalkenyl, (C 2~C 6 ) Alkinyl, (C 1 ~C 6 )alkoxy, (C 1 ~C 6 ) Haloalkyl, (C 3 ~C 6 ) Halocycloalkyl, (C 2 ~C 6 ) Haloalkenil, (C 3 ~C 6 ) Halocycloalkenyl, (C 1 ~C 6 ) Haloalkoxy, S(C 1 ~C 6 )alkyl, S(O)(C 1 ~C 6 ) alkyl, S(O) 2 (C 1 ~C 6 ) alkyl, S(C 1 ~C 6 ) Haloalkyl, S(O)(C 1 ~C 6 ) Haloalkyl, S(O) 2 (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 )alkyl-S(O) 2 NH 2 、(C 1 ~C 6 ) Haloalkyl-S(O) 2 NH 2 Selected from the group consisting of triazolyl; R 14 These are H, F, Cl, Br, I, CN, NH 2 NO 2 、(C 1 ~C 6 ) alkyl, (C 3 ~C 6 )Cycloalkyl, (C 2 ~C 6 ) Alkenil, (C 3 ~C 6 )Cycloalkenyl, (C 2 ~C 6 ) Alkinyl, (C 1 ~C 6 )alkoxy, (C 1 ~C 6 ) Haloalkyl, (C 3 ~C 6 ) Halocycloalkyl, (C 2 ~C 6 ) Haloalkenil, (C 3 ~C 6 ) Halocycloalkenyl, (C 1 ~C 6 ) Haloalkoxy, S(C 1 ~C 6 )alkyl, S(O)(C 1 ~C 6 ) alkyl, S(O) 2 (C 1 ~C 6 ) alkyl, S(C 1 ~C6 ) Haloalkyl, S(O)(C 1 ~C 6 ) Haloalkyl, S(O) 2 (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 )alkyl-S(O) 2 NH 2 and (C 1 ~C 6 ) Haloalkyl-S(O) 2 NH 2 Selected from the group consisting of; R 15 H, (C 1 ~C 6 ) alkyl, (C 2 ~C 6 ) Alkenil, (C 2 ~C 6 ) Alkinyl, (C 1 ~C 6 ) Haloalkyl, (C 1 ~C 6 ) Alkyl(C 1 ~C 6 )alkoxy, C(=O)(C 1 ~C 6 )alkyl, and (C 1 ~C 6 )alkoxy C (=O) (C 1 ~C 6 Selected from the group consisting of alkyl groups; R 16 is, (C 1 ~C 8 ) alkyl, (C 3 ~C 8 )Cycloalkyl, (C 1 ~C 8 )alkyl-O-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 ) Alkyl(C 3 ~C 8 )Cycloalkyl, (C 1 ~C 8 ) Alkylphenyl, (C 2 ~C 8 ) Alkenil, (C 2 ~C 8 ) Alkinyl, (C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 )alkyl-S(O)-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 )alkyl-S(O) 2 -(C 1 ~C 8 )alkyl, O-phenyl, O-(C 2 ~C 8 ) Alkenyl, O-(C 1 ~C 8 ) Alkyl(C 3 ~C 8 )Cycloalkyl, O-(C 1 ~C 8 ) Alkylphenyl, (C 1 ~C 8 )alkyl-O-(C 1 ~C 8 ) Alkyl(C 3 ~C 8 )Cycloalkyl, (C 1 ~C 8 )alkyl-O-(C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl~C(=O)NH-(C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-NHC(O)-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 )alkyl-S-(C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S(O)-(C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S(O) 2 -(C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S(O) 2 -NH 2 and selected from the group consisting of heteroalgebras, Here, each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, haloalkyl, and phenyl are F, Cl, Br, I, CN, OH, NH 2 NO 2 、(C 1 ~C 8 ) alkyl, (C 2 ~C 8 ) Alkenil, (C 2 ~C 8 ) Alkinyl, (C 1 ~C 8 )alkoxy, (C 1 ~C 8 ) Haloalkyl, N((C 1 ~C 8 )alkyl) 2 , C(O)O(C 1 ~C 8 ) It may be optionally substituted with one or more substituents selected from the group consisting of alkyl, benzothioenyl, oxoimidazolidinyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl; The aforementioned heterocycle is selected from the group consisting of azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinyl, imidazolidinyl, isoxazolidinyl, morpholinyl, oxazolidinyl, oxetanyl, piperadinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinyl, and Each (C 3 ~C 8 )Cycloalkyl and heterocycles are H, F, Cl, Br, I, CN, NH 2 NO 2 , oxo, (C 1 ~C 4 ) alkyl, (C 2 ~C 8 ) Alkenil, (C 2 ~C 8 ) Alkinyl, (C 1 ~C 4 ) Haloalkyl C(=O)O(C 1 ~C 4 )alkyl, (C=O)NH(C 1 ~C 4 )alkyl, (C=O)NH(C 1 ~C 4 ) Haloalkyl, C(=O)(C 3 ~C 6 )Cyclopropyl, C(=O)(C 1 ~C 4 ) Haloalkyl, C(=O)(C 1 ~C 4 ) Alkyl(C 1 ~C 4 )alkoxy and (C 1 ~C 4 ) may be optionally substituted with one or more substituents selected from the group consisting of alkyl-morpholinyl, R 15 and R 16 Together, they can optionally form a 2- to 5-membered saturated or unsaturated hydrocarbyl bond which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen. Here, the hydrocarbyl bond is F, Cl, Br, I, CN, NH 2 and NO 2 They may be optionally substituted with one or more substituents selected from the group consisting of; Q 1 and Q 2 Each is independently selected from the group consisting of O and S. Compounds and N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystalline polymorphs, isotopes, stereoisomers, and tautomers. [2] R 16 However, (C 1 ~C 8 ) alkyl, (C 3 ~C 8 )Cycloalkyl, (C 1 ~C 8 )alkyl-O-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 ) Alkyl(C 3 ~C 8 )Cycloalkyl, (C 2 ~C 8 ) Alkenil, (C 2 ~C 8 ) Alkinyl, (C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 )alkyl-S(O)-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 )alkyl-S(O) 2-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 )alkyl-O-(C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S-(C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S(O)-(C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S(O) 2 -(C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S(O) 2 -NH 2 , as well as selected from the group consisting of complex algebras, R 16 Each alkyl, alkenyl, alkynyl, alkyl-cycloalkyl, and haloalkyl is F, Cl, Br, I, CN, OH, NH 2 NO 2 、(C 1 ~C 8 ) alkyl, (C 2 ~C 8 ) Alkenil, (C 2 ~C 8 ) Alkinyl, (C 1 ~C 8 )alkoxy, (C 1 ~C 8 ) Haloalkyl, C(O)O(C 1 ~C 8 ) It may optionally be substituted with one or more substituents selected from the group consisting of alkyl, oxoimidazolidinyl, furanyl, and pyrazolyl; Each (C 3 ~C 8 )Cycloalkyl groups include H, F, Cl, Br, I, CN, NH 2 NO 2 , oxo, (C 1 ~C 4 ) alkyl, (C 2 ~C 8 ) Alkenil, (C 2 ~C 8 ) Alkinyl, (C 1 ~C 4 ) Haloalkyl, C(=O)O(C 1 ~C 4 )alkyl, (C=O)NH(C 1 ~C 4 )alkyl, (C=O)NH(C 1 ~C 4 ) Haloalkyl, C(=O)(C 3 ~C 6 )Cyclopropyl, C(=O)(C 1 ~C 4 ) Haloalkyl, C(=O)(C 1 ~C 4 ) Alkyl(C 1 ~C 4 )alkoxy and (C 1 ~C 4 ) It may be optionally substituted with one or more substituents selected from the group consisting of alkyl-morpholinyl, The heterocycle is selected from the group consisting of azetidinyl, imidazolidinonyl, isoxazolidinonyl, oxetanyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydrothiophenyl oxide. R 16 Each of these heterocycles is H, F, Cl, Br, I, CN, oxo, (C 1 ~C 4 ) alkyl, (C 2 ~C 8 ) Alkenil, (C 2 ~C 8 ) Alkinyl, (C 1 ~C 4 ) Haloalkyl, (C=O)NH(C 1 ~C 4 )alkyl, (C=O)NH(C 1 ~C 4 ) Haloalkyl, and C(=O)(C 1 ~C 4 ) Alkyl(C 1 ~C 4 The compound for use as described in [1] may optionally be substituted with one or more substituents selected from the group consisting of alkoxys. [3] R 16 However, (C 1 ~C 8 ) alkyl, (C 3 ~C 8 )Cycloalkyl, (C 1 ~C 8 ) Alkyl(C 3 ~C 8 )Cycloalkyl, (C 2 ~C 8 ) Alkenil (C 2 ~C 8 ) Alkinyl, (C 1 ~C 8 ) Haloalkyl, (C 1 ~C 8 )alkyl-S-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 )alkyl-S(O)-(C 1 ~C 8 ) alkyl, (C 1 ~C 8 )alkyl-S(O) 2 -(C 1 ~C 8 )alkyl, and (C 1 ~C 8 )alkyl-O-(C 1 ~C 8 ) Selected from the group consisting of haloalkyl groups; Each alkyl, cycloalkyl, alkenyl, alkynyl, and haloalkyl is F, Cl, Br, (C 1 ~C 8 ) alkyl, (C 2 ~C 8 ) Alkenil, (C 2 ~C 8 ) Alkinyl, (C 1 ~C 8 )alkoxy, C(O)O(C 1 ~C 8 ) may be optionally substituted with one or more substituents selected from the group consisting of alkyl and oxoimidazolidinyl. Said (C 3 ~C 8 )Cycloalkyl groups include H, F, Cl, Br, I, CN, NH 2 NO 2 , oxo, (C 1 ~C 4 ) alkyl, (C 2 ~C 8 ) Alkenil, (C 2 ~C 8 ) Alkinyl, (C 1 ~C 4 ) Haloalkyl, (C=O)NH(C 1 ~C 4 )alkyl and (C=O)NH(C 1 ~C 4 ) It may be optionally substituted with one or more substituents selected from the group consisting of haloalkyl groups. [4] A compound for use as described in any one of [1] to [3], wherein Q1 and Q2 are O. [5] R 5 However, H is; R 6 However, H is; R 7 However, it is selected from the group consisting of Cl and Br; R 8 However, it is selected from the group consisting of Cl and Br; R 9 、R 10 , and R 11 A compound for use as described in any one of the items [1] to [4], wherein H is present. [6] R 13 However, H, F, Cl, CH 3 and CF 3 A compound for use as described in any one of the following items, selected from the group consisting of [1] to [5]. [7] R 12 However, H, F, Cl, Br, CH 3 A compound for use as described in any one of the following items, selected from the group consisting of [1] to [6]. [8] R 14 A compound for use as described in any one of [1] to [7], wherein the compound is H or F. [9] R 15 However, H and CH 3 A compound for use as described in any one of the following items, selected from the group consisting of [1] to [8].

[10] The compound for use according to any one of [1] to [9], wherein the parasitism of the parasite is that of a sea louse.

[11] The compound for use according to any one of [1] to

[10] , wherein the parasite is at least one of Lepeophtheirus salmonis, Caligus celmensi, Caligus curtus, Caligus dussumieri, Caligus elongates, Caligus longicaudatus, Caligus rogercresseyi, or Caligus stromii.

[12] The compound for use according to any one of [1] to

[11] , wherein the parasitism of the parasite is copepod, pre-adult or adult sea lice, or a mixed parasitism at various stages.

[13] The compound for use according to any one of [1] to

[12] , wherein the parasitic rate in the fish is 0.5 to 3 per fish in the fish facility on average, and preferably the parasitic organism is an adult female sea louse.

[14] The compound for use according to any one of items [1] to

[13] , wherein the method comprises administering the compound of formula (I) described in any one of items [1] to

[10] to a fish by oral administration, local administration such as bath treatment, or intraperitoneal or intramuscular injection.

[15] The compound for use according to any one of [1] to

[14] , wherein the method comprises administering a compound of formula (I) as defined in any one of [1] to

[10] to a fish by oral administration, wherein the oral administration comprises administering a medicinal fish feed containing a therapeutically effective amount of the compound and fish feed.

[16] The compound for use according to any one of [1] to

[15] , wherein the method comprises administering a compound of formula (I) as defined in any one of [1] to

[10] by a bath treatment, wherein the bath treatment comprises immersion of a fish in water containing a therapeutically effective amount of the compound.

[17] The compound for use according to any one of [1] to

[16] , wherein the fish is salmon.

[18] A premix comprising a compound of formula (I) as described in any one of items [1] to

[10] , further comprising nutrients.

[19] The premix according to

[18] , wherein the premix contains nutrients in the form of pellets, and the pellets are coated with a composition comprising a compound of formula (I) as described in any one of [1] to

[10] .

[20] A medicinal fish feed comprising the premix described in

[18] or 19 and fish feed.

Claims

[Claim 1] the below described: A fish parasite control agent comprising a compound selected from or its N-oxide, a veterinarily acceptable acid addition salt, solvate, crystalline polymorph, isotope, or tautomer.

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