Cyclopropylamide compounds against parasites in fish

A method to control parasite infestations in fish comprising administering to a fish a compound of the following formula

• and N-oxides, veterinary acceptable acid addition salts, solvates, isotopes, stereoisomers, and tautomers, wherein
• R1 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;
• R2 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, (C1-C6)haloalkyl-S(O)2NH2, and S-(Halo)5;
• R3 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, (C1-C6)haloalkyl-S(O)2NH2, and S-(Halo)5;
• R4 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, (C1-C6)haloalkyl-S(O)2NH2, and S-(Halo)5;
• R5 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;
• R6 is selected from the group consisting of H and (C1-C6)alkyl;
• R7 is selected from the group consisting of H, F, Cl, Br, and I;
• R8 is selected from the group consisting of F, Cl, Br, and I;
• R9 is selected from the group consisting of H and (C1-C6)alkyl;
• R10 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;
• R11 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;
• R12 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;
• R13 is selected from the group consisting of 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, (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;
• R14 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;
• R15 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)(C-C6)alkyl;
• R16 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 a heterocycle,
• wherein 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,
• and wherein the heterocycle is selected from the group consisting of, azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinonyl, imidazolidinonyl, isoxazolidinonyl, morpholinyl, oxazolidinonyl, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinonyl, and
• wherein 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-morpholinylR15 and R16 together can optionally form a 2- to 5-membered saturated or unsaturated, hydrocarbyl link, which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen,
• wherein said hydrocarbyl link may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NH2, and NO2;
• Q1 and Q2 are each independently selected from the group consisting of O and S.