• 专利附录
  • 专利说明
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    • 专利摘要:
    A compound represented by Formula (1) is provided can be used as an agent for the prolonged control of ectoparasites for an animal. A preparation for systemic application is provided for use in prolonged control of an ectoparasite in an animal including the compound. A method for the prolonged control of an ectoparasite in an animal includes the systemic application of the compound. The compound can be used for the preparation of a drug for the prolonged control of an ectoparasite in an animal. A horticultural or agricultural insecticide containing the compost, and a method of protecting a crop from a harmful organism is also provided.
    公开号:BR112020005628A2
    申请号:R112020005628-6
    申请日:2018-09-19
    公开日:2020-10-13
    发明作者:Yoji Aoki；Shinichi Banba；Markus Berger；Lars Baerfacker
    申请人:Mitsui Chemicals Agro, Inc.；
    IPC主号:
    专利说明:

    [0001] [0001] The present invention is related to the use of a specific carboxamide derivative in the prolonged control of ectoparasites in animals by systemic application of said compound to said animal and the preparations for said use.
    [0002] [0002] WO 2005/073165, WO 2010/018714 and WO 2011/093415 reveal certain carboxamide derivatives and their pesticidal activities. Methods for the synthesis of these compounds, as well as certain intermediates, are described in WO 2010/013567 and WO 2010/018857. In addition, pest control compositions containing carboxamide derivatives in combination with other compounds are described in WO 2007/013150. SUMMARY
    [0003] [0003] Surprisingly, we found that the compound as disclosed in this specification shows excellent activity with regard to the protection of harmful organisms. In particular, we found that the compound has an excellent insecticidal activity, and we also found that the compound has a long-acting activity against ectoparasites through systemic application to animals, and are therefore suitable for prolonged control of ectoparasites in animals. Based on these findings, the present disclosure provides an agent for the prolonged control of ectoparasites for an animal, a preparation for systemic application for use in the prolonged control of an ectoparasite in an animal, a method for the prolonged control of an ectoparasite in an animal , use of the compound as revealed in this specification for the preparation of a medicine for the prolonged control of an ectoparasite in an animal, a horticultural or agricultural insecticide, a method of protecting a crop from a harmful organism, a composition that includes the compound as disclosed in that specification mixed with an inert carrier and an optional auxiliary agent, a mixture that includes the compound as disclosed in that specification combined with at least one other insecticide and / or fungicide, and a compound represented by a specific chemical formula.
    [0004] [0004] The present invention is related to the following aspects.
    [0005] [0005] [1] An agent for the long-term control of ectoparasites for an animal represented by the following Formula (1): Ro o 'CF3
    [0006] [0006] [2] The agent for the prolonged control of ectoparasites according to [1], where each of A; and the; independently represents a group
    [0007] [0007] [3] The agent for the long-term control of ectoparasites according to [1] or [2], in which the agent for the long-term control of ectoparasites is applied systemically via an oral route.
    [0008] [0008] [4] The agent for the long-term control of ectoparasites according to [1] or [2], in which the agent for the long-term control of ectoparasites is applied systemically via a parenteral route.
    [0009] [0009] [5] The agent for the long-term control of ectoparasites according to [1] or [2], wherein the agent for the long-term control of ectoparasites is applied systemically via a dermal route.
    [0010] [0010] [6] A preparation for systemic application for use in the prolonged control of an ectoparasite in an animal, the preparation including the compound represented by Formula (1).
    [0011] [0011] [7] The preparation according to [6], in which the preparation is for oral use.
    [0012] [0012] [8] The preparation according to [6], wherein the preparation is for parenteral use.
    [0013] [0013] [9] The preparation according to [6], in which the preparation is for dermal use.
    [0014] [0014] [10] The preparation according to any one of [6] to [9], wherein the preparation is a single dose preparation.
    [0015] [0015] [11] A method for the prolonged control of an ectoparasite in an animal, including the systemic application of the compound represented by Formula (1).
    [0016] [0016] [12] Use of the compound represented by Formula (1), for the preparation of a medicine for the prolonged control of an ectoparasite in an animal, in which the said medicine is applied systemically to said animal.
    [0017] [0017] [13] A horticultural or agricultural insecticide containing the compound represented by Formula (1) as an active ingredient.
    [0018] [0018] [14] A method of protecting a crop from a harmful organism, the method including treating a crop or soil for cultivation with an effective amount of the compound represented by Formula (1).
    [0019] [0019] [15] A composition that includes the compound represented by Formula (1) mixed with an inert carrier and, optionally, with an auxiliary agent.
    [0020] [0020] [16] A mixture that includes the compound represented by Formula (1) combined with at least one other insecticide and / or fungicide.
    [0021] [0021] [17] A compound represented by the following Formula (2): in which
    [0022] [0022] [18] The compound according to [17], wherein the compound is selected from the group consisting of N- (2-fluoro- 3- ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) carbamoyl) phenyl) -6- (trifluoromethyl) nicotinamide, N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) carbamoyl) phenyl) -N-methyl-6- (trifluoromethyl) nicotinamide, 6-fluoro-N- (2-fluoro-3 - ((2- iodo-4- (perfluoropropan-2-yl) -6- ( trifluoromethyl) phenyl) carbamoyl) phenyl) nicotinamide, 6-fluoro-N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) carbamoyl) phenyl) -N-methylnicotinamide,
    [0023] [0023] According to the present disclosure, an agent for the prolonged control of ectoparasites for an animal, a preparation for systemic application for use in the prolonged control of an ectoparasite in an animal, a method for the prolonged control of an ectoparasite in an animal, use of the compound as revealed in this specification for the preparation of a medicine for the prolonged control of an ectoparasite in an animal, a horticultural or agricultural insecticide, a method of protecting a crop from a harmful organism, a composition that includes the compound as disclosed in that specification mixed with an inert carrier and an optional auxiliary agent, a mixture that includes the compound as disclosed in that specification combined with at least one other insecticide and / or fungicide, and a compound represented by a specific chemical formula, can be provided. DETAILED DESCRIPTION
    [0024] [0024] In the present disclosure, a compound represented by the following Formula (1) can be used for various applications, as described in that specification. Xs and the 'CF3 Er xs X2 CF PO Xa "Ko see
    [0025] [0025] In Formula (1),
    [0026] [0026] The terms used in the formulas, including Formula a (1), have the meanings as described below.
    [0027] [0027] As used in this specification, the terms "n%," Ni "," s- ", and" t "mean" normal- "," iso "," secondary- "and" tertiary- ", respectively.
    [0028] [0028] The term "halogen atom" in the present invention represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
    [0029] [0029] The term "haloalkyl C1i-Ca group" in the present invention represents, for example, a linear or branched alkyl group having 1 to 4 carbon atoms substituted with one or more halogen atoms that can be the same or different ones from others, for example, trifluoromethyl, pentafluorethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, 2,2-difluorethyl, 2,2-dichloroethyl, 2,2,2-trifluorethyl, 2-7 fluorethyl, 2-chloroethyl , 2-bromoethyl, 2-iodoethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl, l1-chloro-3 -fluoro-2-propyl, 1,1,1-trifluoro-2-propyl, 2,3,3, 3-tetrafluoro-n-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl , 1,1,1,3,3,3-hexafluoro-2-
    [0030] [0030] The term "C1-Ca alkoxy group" in the present invention represents, for example, a linear or branched alkoxy group having 1 to 4 carbon atoms, for example, methoxy, ethoxy, n-propoxy, i-propoxy , n-butoxy, i-butoxy, s-butoxy or t-butoxy.
    [0031] [0031] The term "haloalkoxy C1i-Ca group" in the present invention represents, for example, a linear or branched alkoxy group having 1 to 4 carbon atoms substituted with one or more halogen atoms that can be the same or different ones others, for example, difluoromethoxy, trifluoromethoxy, pentafluorethoxy, heptafluoro-n-propoxy, heptafluoro-i-propoxy, 2,2-difluorethoxy, 2,2-dichloroethoxy, 2,2,2-trifluorethoxy, 2-fluorethoxy, 2- chloroethoxy, 27 bromoethoxy, 2-iodoethoxy, 2,2,2-trichloroethoxy, 2,2,27 tribromoethoxy, 1,3-difluoro-2-propoxy, 1,3-dichloro-2-propoxy, 1-chloro-3- fluoro-2-propoxy, 1,1,1-trifluoro-2-propoxy, 2,3,3,3-tetrafluoro-n-propoxy, 1,1,1,3,3,3-hexafluoro-2-propoxy, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propoxy, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propoxy, 1,1,2, 3,3,3-hexafluoro-2-chloro-n-propoxy, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propoxy, 1,1,2,3,3,3- hexafluoro-1-
    [0032] [0032] The term "C1-C alkylthio group" in the present invention represents, for example, a linear or branched alkylthio group having 1 to 4 carbon atoms, for example, methylthio, ethylthio, n-propylthio, i-propylthio , n-butylthio, i-butylthio, s-butylthio or t-butylthio.
    [0033] [0033] The term "haloalkylthio C1i-Cs group" in the present invention represents, for example, a linear or branched alkylthio group having 1 to 4 carbon atoms substituted with one or more halogen atoms which can be the same or different from each other from others, for example, difluoromethylthio, trifluoromethylthio, pentafluorethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, 2.27 difluorethylthio, 2,2-dichlorethylthio, 2,2,2-trifluorethylthio, 2-fluorethylthio, 2-chloroethylthio, 2-chloroethylthio , 2-bromoethylthio, 27 iodoethylthio, 2,2,2-trichlorethylthio, 2,2,2-tribromoethylthio, 1,3-difluoro-2-propylthio, 1,3-dichloro-2-propylthio, 1-chloro-3- fluoro-2-propylthio, 1,1,11-trifluoro-2-propylthio, 2,3,3,3-tetrafluoro-n-propylthio, 1,1,1,3,3,3-hexafluoro-2-propylthio, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylthio, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propylthio, 1,1,2, 3,3,3-hexafluoro-2-chloro-n-propylthio, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propylthio, 1,1,2,3,3,3- hexafluoro-11-bromo-2-propylthio, 2,2,3,3, 3-pentafluoro-n-propylthio, 3-fluoro-n-propylthio, 3-chloro-n-propylthio, 3-bromo-n-propylthio,
    [0034] [0034] The term "C1-Ca alkylsulfipinyl group" in the present invention represents, for example, a linear or branched alkylsulfinyl group having 1 to 4 carbon atoms, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfiphyl , n-butylsulfinyl, i-butylsulfinyl, s-butylsulfinyl or t-butylsulfinyl.
    [0035] [0035] The term "C1i-C4 haloalkylsulfinyl group" in the present invention represents, for example, a linear or branched alkylsulfinyl group having 1 to 4 carbon atom substituted with one or more halogen atoms which can be the same or different ones from others, for example, difluoromethylsulfinyl, trifluoromethylsulfifinyl, pentafluorethylsulfifinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, 2,2-difluorethylsulfinyl, 2,2-dichlorethylsulfinyl, 2,2,2-trifluorine, 2,2,2-trifluorine -chloroethylsulfinyl, 2-7 bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 2,2,2-tribromoethylsulfinyl, 1,3-difluoro-2-propylsulfinyl, 1,3-dichloro-2-propylsulfinyl, 1- chloro-3-fluoro-2-propylsulfinyl, 1,1,1-trifluoro-2-propylsulfinyl, 2,3,3,3-tetrafluoro-n-propylsulfifinyl, 1,1,1,3,3,3-hexafluoro- 2-propylsulfifinyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylsulfifinyl, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propylsulfinyl, 1, 1,2,3,3,3-hexafluoro-2-clo ro-n-propylsulfinyl, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propylsulfinyl, 1,1,2,3,3,3-
    [0036] [0036] The term "C1i-Ca alkylsulfonyl group" in the present invention represents, for example, a linear or branched alkylsulfonyl group having 1 to 4 carbon atoms, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl , n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl or the like.
    [0037] [0037] The term "C1i-C4 haloalkylsulfonyl group" in the present invention represents, for example, a linear or branched alkylsulfonyl group having 1 to 4 carbon atoms substituted with one or more halogen atoms that can be the same or different ones others, for example difluoromethylsulfonyl, trifluoromethylsulfonyl, pentafluorethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, 2,2-difluorethylsulfonyl, 2,2-dichlorethylsulfonyl, 2,2,2-trifluorethyl, 2-trifluorethylsulfonyl -chlorethylsulfonyl, 2-7 bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2,27 trichloroethylsulfonyl, 2,2,2-tribromoethylsulfonyl, 1,3-difluoro-2-propylsulfonyl, 1,3-dichloro-2-propylsulfonyl, 1-chlorine -3-fluoro-2-propylsulfonyl, 1,1,1-trifluoro-2-propylsulfonyl, 2,3,3,3-tetrafluoro-n-propylsulfonyl, 1,1,1,3,3,3-hexafluoro-2 -propylsulfonyl, 1,1,1,3,3,3-
    [0038] [0038] The compound represented by Formula (1) according to the present invention can include one or more chiral carbon atoms or chiral centers in their structural formulas and, thus, two or more optical isomers (enantiomers or diastereomers) may exist . However, the scope of the present invention each includes optical isomers and mixtures thereof in any proportions.
    [0039] [0039] In Formula (1), preferred definitions of substituents include the following: Preferably, X represents a fluorine atom or a trifluoromethyl group.
    [0040] [0040] Preferably, Ri represents a hydrogen atom or a methyl group.
    [0041] [0041] Preferably, X1 represents a hydrogen atom or a fluorine atom.
    [0042] [0042] In one embodiment, the compound represented by Formula (1) is a compound in which each of A; and A3 independently represents a group C-X1, A; represents a nitrogen atom or a C-Xi group, As represents a C-X1 group, Ri represents a hydrogen atom or a C1-Ca alkyl group, R2z represents a trifluoromethyl group: X represents a halogen atom or a C1 group -C'a haloalkyl, X1 represents a hydrogen atom, each of X> and X. represents a fluorine atom, X3; represents a hydrogen atom, Xs represents a bromine atom or an iodine atom, and Y represents a single bond or a sulfonyl group.
    [0043] [0043] Examples of the compound represented by Formula (1 that can be used in the present invention include the compounds listed in Table 1. The compounds listed in Table 1 are represented by the following Formula (Formula (1)), in which Ri is CH3a, R2 is CF3, X2 is F, X3 is H, Xa is F, X5 is 1, Y is a single bond, and A1, Az, A3, A, and X are as shown in Table 1. Ro, A 'CF;
    [0044] [0044] The present disclosure also includes Tables 2 to 240 below. Each of Tables 2 to 240 lists multiple compounds that are within the scope of Formula (1), similar to Table 1. More specifically, each of Tables 2 to 240 lists the same combinations of A: i, Az, A3, As and X as the combinations listed in Table 1, but the combination of Ri, Ro, X> 2, X3, Xa, Xs EY in each of Tables 2 to 240 differs from that in Table 1. Therefore, only the combinations of Ri, Ro, X2, X3, Xa, X5 € Y in the respective Tables are indicated below, and the indication of the variations of the combination of A: 1, As, Az, A, EX in each Table is omitted, as the variations are the same as those listed in Table 1.
    [0045] [0045] In Table 1, the combination of Ri, Ro, X2, X3, Xa, Xs and Y is such that “Ri is CH3, Ro is CF3, X2 is F, X3 is H, Xa is F, Xs is IT , eY is a simple link ”. The combination of Ri, Ro, X2o, X3, Xa, Xs EY in Table 2 is such that "R; i is H, Ro is CF3, Xo is F, X; 3 is H, Xa Is F, Xs is I, and Y is a simple bond ”, as indicated below. Thus, the first entry in Table 2 specifically reveals the compound 2-fluoro-3- (4-fluorobenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide , which is a compound in which A, is CH, A; is CH, A; is CH, As is CH, X is F, R1 is H, Ro is CF3, Xx> is F, X; 3 is H, Xa Is F, X5s Is I, and Y is a single bond. Note that the first entry in Table 1 indicates “A; is CH, A; is CH, A; is CH, A is CH, X is F ”/. The compound specified in the second and subsequent entries in Table 2 can also be identified in the same way, and the compounds listed in Tables 3 to 240 can also be identified in the same way, taking into account the combination of Ri, Ro, X2, X3, Xa, X5 EY for each Table. Combination of Ri, Ro, X2, X3, Xa, Xs and Y in each Table Table> R: is H, Ro is CF3, Xo is F, X3 is H, Xa is EF, Xs is 1, EY is a single bond 3 R; 1 is CH3a, Ro is CF3, X2 is F, X3 is H, Xa is F, X5s is Br and Y is a single bond 4 R1 is H, Ro is CF3, Xo is F, X3 is H, Xa É F, X5s É Br and Y is a simple bond Ri is CH3, Ro is CF3, X2 is F, X3 IS H, Xa IS EF, Xs IS IT and rYéo 6 R: i is H, R2 is CF3, Xo is F, X3 is H, Xa is FE, X5s is ID and Yéo 7 R; 1 is CH3a, Ro is CF3, X2o is F, X3 is H, Xa is F, Xs is Br evreo 8 R ;: is H, Ro is CF3, Xo is F, X3 is H, Xa is F, X5s is Br and rYéo
    [0046] Preferred examples of compounds represented by Formula (1) that can be used in the present invention include the compounds shown in Table 241 below. Table 241 Composite Structure Composite Structure ATA A, bbkbkbkDIIOTT — I) & - ÉI — E RT ———— in F 2 F. AND LO F, F: YE. e O Br FF 10 Fr efe Br FF
    [0047] [0047] Particularly preferred compounds represented by Formula (1) for use according to the present invention include the following compounds: 2-fluoro-3- (4-fluoro-N-methylbenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide 2-fluoro-3- (4-fluorobenzamido) -N- (2-iodo-4- (perfluoropropan- 2-11) -6- (tri fluoromethyl ) phenyl) benzamide.
    [0048] [0048] The compound represented by Formula (1) can be in the form of a solid, or in the form of a solvate, in particular a hydrate. The compound in the form of a solvate, particularly hydrate, is also encompassed by the invention.
    [0049] [0049] Compounds represented by Formula (1) can be prepared using methods known in the art; see, for example, WO 2005/073165, WO 2010/018714, WO 2011/093415, as well as WO 2010/013567 and WO 2010/018857. Exemplary synthesis methods will be detailed in Examples 1 to 9.
    [0050] [0050] In the field of animal health, that is, in the field of veterinary medicine, the compound represented by Formula (1) is active against animal parasites, in particular, ectoparasites or endoparasites. The term "endoparasite" includes, in particular, helminths and protozoa, for example, coccids. Ectoparasites are - typically and preferably - arthropods, in particular insects and mites. Depending on the toxicity of the compound represented by Formula (1) against animal parasites, the compound represented by Formula (1) can be used to control animal parasites. In particular, the compound represented by Formula (1) has a prolonged effect in relation to the control of ectoparasites, as demonstrated in the working examples described later. The prolonged effect can provide, for example, at least 50% reduction (more preferably at least 60% reduction, even more preferably at least 70% reduction, even more preferably at least 80% and, particularly, preferably at least 90 %) in the number of live pests, compared with an untreated control for, for example, at least 16 days (more preferably at least 23 days, and even more preferably, at least 30 days). The test used to determine the prolonged effect can be performed by reference to Test Examples E and F described later.
    [0051] [0051] In the field of veterinary medicine, the compound represented by Formula (1) has properties suitable for the control of parasites that occur in animal breeding and livestock in farmed, breeding, zoo, laboratory, experimental and domestic animals, and the compound represented by Formula (1) has low toxicity against warm-blooded animals. They are active against all specific stages or stages of parasite development.
    [0052] [0052] According to one modality, an extended ectoparasite control agent is provided for an animal represented by Formula (1). In other words, the compound represented by Formula (1) can be used appropriately as an extended ectoparasite control agent for an animal.
    [0053] [0053] The agent for the prolonged control of ectoparasites can have a chemical structure in which: each of A; and the; independently represents a C-X group :; Az represents a nitrogen atom or a C-Xi group; As represents a C-Xi group; R 'represents a hydrogen atom or a C1-C's alkyl group; R2z represents a trifluoromethyl group: X represents a halogen atom or a C1i-Ca haloalkyl group; X; represents a hydrogen atom; each of X; and X 'represents a fluorine atom; X3; represents a hydrogen atom; Xs represents a bromine atom or an iodine atom; and Y represents a single bond or a sulfonyl group. The agent for the prolonged control of ectoparasites can be applied systemically, and the application can be carried out through at least one oral route, a parenteral route or a dermal route.
    [0054] [0054] According to another modality, a preparation for systemic application is provided for use in the prolonged control of an ectoparasite in an animal, the preparation including the compound represented by Formula (1). The preparation can be for at least one for oral use, parenteral use or dermal use. The preparation can be a single dose preparation. In the present disclosure, the term "preparation" and the term "formulation" are used in a substantially interchangeable manner.
    [0055] [0055] According to another modality, a method is provided for the prolonged control of an ectoparasite in an animal, the method including the systemic application of the compound represented by Formula (1). According to another modality, the use of the compound represented by Formula (1) is provided for the preparation of a medication for the prolonged control of an ectoparasite in an animal, in which the medication is applied systemically to the animal. According to yet another modality, the use of the compound represented by Formula (1) is provided for the prolonged control of an ectoparasite in an animal, in which the drug is applied systemically to the animal.
    [0056] [0056] Farm animals that can be treated with the compound represented by Formula (1) for the control of parasites include, for example, mammals, for example sheep, goats, horses, Monkeys, camels, buffalo, rabbits, reindeer , antelopes and, in particular, cattle and pigs; or farmed birds such as turkeys, ducks, geese and, in particular, chickens; or fish or crustaceans for example, in aquaculture; or, as the case may be, insects such as bees.
    [0057] [0057] Domestic animals that can be treated with the compound represented by Formula (1) for the control of parasites include, for example, mammals, for example, hamsters, guinea pigs, rats, chinchilla mice, ferrets or, in particularly, dogs, cats; captivity birds; reptiles; amphibians or aquarium fish.
    [0058] [0058] According to one embodiment, the compound represented by Formula (1) is administered to a mammal. According to another modality, the compound represented by Formula (1) is administered to a bird, for example, a captive bird or, in particular, poultry.
    [0059] [0059] By using the compound represented by Formula (1) for the control of animal parasites, it is possible to reduce or avoid illness, cases of death and performance reductions (in the case of meat, milk, wool, skins, eggs, honey) and the like), so that more economical and simpler breeding is possible and better animal welfare can be achieved.
    [0060] [0060] The term "control" or "that controls", as in this specification in relation to the field of animal health, means reducing the incidence of the respective parasite in an animal infected with these parasites to innocuous levels. More specifically, “control”, as used in this specification, means effectiveness in the death of the respective parasite, inhibiting its growth or inhibiting its proliferation.
    [0062] [0062] Furthermore, exemplary arthropods that can be controlled using the compound represented by Formula (1) include the following mites, without any limitation: from the subclass of Acari (Acarina) and the order of Metastigmata, for example, from the Argasidae family like Argas spp., Ornithodorus spp., Otobius spp., from the family of Ixodidae like Amblyomma spp., Dermacentor spp., Haemaphysalis spp.,
    [0063] [0063] Exemplary parasitic protozoans that can be controlled using the compound represented by Formula (1) include, without limitation: Mastigophora (Flagellata) such as: Metamonada: of the order Diplomonadida, for example, Giardia spp. and Spironucleus sSpp., Parabasala: of the order Trichomonadida, for example, Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., and Tritrichomonas Spp., and Euglenozoa: of the order Trypanosomatida, for example, Leishmania sp. and Trypanosoma sSpp .; Sarcomastigophora (Rhizopoda), such as, for example, Entamoebidae, for example, Entamoeba spp., Centramoebidae, for example, Acanthamoeba sp., And Euamoebidae, for example, Hartmanella sp .; Honeycomb, such as Apicomplexa (Sporozoa):
    [0064] [0064] Helminths pathogenic to humans or animals that can be controlled using the compound represented by Formula (1) include, for example, acanthocephali, nematodes, pentastomids and flatworms (eg monogens, cestodes and trematodes). Exemplary helminths that can be controlled using the compound represented by Formula (1) include, without limitation: Monogenes: for example: Dactylogyrus SPpP., Gyrodactylus spp., Microbothrium spp., Polystoma SPpp., Troglocephalus Spp .; Cestodes, including: of the order of Pseudophyllidea, for example, Bothridium sPpp., Diphyllobothrium spP., Diplogonoporus spp., Ichthyobothrium spp., Ligula spp., Schistocephalus spp. and Spirometra Spp.,
    [0065] [0065] In the veterinary field and in the maintenance of animals the administration of the compound represented by Formula (1) is carried out by methods generally known in the art, for example, enterally, parenterally, dermally or nasally in the form of suitable preparations. Administration can be carried out prophylactically or therapeutically. Administration can be carried out systemically.
    [0066] [0066] Accordingly, according to one embodiment of the present invention, a compound represented by Formula (1) is provided for use as a medicament. According to another embodiment, a compound represented by Formula (1) is provided for use with an anti-parasitic agent. According to another embodiment, a compound represented by Formula (1) is provided for use as an anthelmintic agent, more particularly for use as a nematicidal agent, a platyelminticidal agent, an acanthocephalic agent or a pentastomicidal agent. According to another embodiment, a compound represented by Formula (1) is provided for use as an antiprotozoal agent. According to another embodiment, a compound represented by Formula (1) is provided for use as an antiectoparasitic agent, particularly an arthropodicidal agent, more particularly an insecticidal or acaricidal agent.
    [0067] [0067] According to an additional embodiment, a veterinary formulation is provided which includes an effective amount of at least one compound represented by Formula (1) and at least one of a pharmaceutically acceptable excipient (for example, a solid or liquid diluent) , a pharmaceutically acceptable auxiliary (for example, a surfactant). In particular, a veterinary formulation is provided that includes an effective amount of at least one compound represented by Formula (1) and a pharmaceutically acceptable and / or pharmaceutically acceptable auxiliary excipient that is normally used in veterinary formulations.
    [0068] [0068] According to another embodiment, a method is provided for the preparation of a veterinary formulation as described in that specification, the method including a step of mixing at least one compound represented by Formula (1) with at least one of a pharmaceutically acceptable excipient or a pharmaceutically acceptable auxiliary. The at least one of a pharmaceutically acceptable excipient or a pharmaceutically acceptable auxiliary can be selected from those commonly used in veterinary formulations.
    [0069] [0069] According to another modality, a veterinary formulation is provided that includes a compound represented by Formula (1), which functions as at least one of an ectoparasiticide formulation or an endoparasitic formulation. The veterinary formulation can function as at least one selected from the group of anthelmintic, antiprotozoal and arthropodicidal formulations and, more specifically, at least one selected from the group of nematicidal, platihelminticide, acanthocephalicide, pentastomycide, insecticide and acaricide formulations, depending on the modalities, as well as their methods of preparation.
    [0070] [0070] According to another modality, a method is provided for the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites, which includes the application of an effective amount of a compound represented by the Formula (1) to an animal, in particular a non-human animal, that needs it.
    [0071] [0071] According to another modality, a method is provided for the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites, which includes the application of the veterinary formulation as defined in this specification to a animal, in particular a non-human animal, that needs it.
    [0072] [0072] According to another modality, the use of a compound represented by Formula (1) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites, in an animal, in particular, is provided a non-human animal.
    [0073] [0073] In the present context of animal health or the veterinary field, the scope of the term "treatment" includes prophylactic treatment, metaphylactic treatment, as well as therapeutic treatment.
    [0074] [0074] IN another embodiment, the present invention provides a pharmaceutical combination ("combination", sometimes also called "mixture"), in particular a veterinary combination, comprising: - one or more compounds represented by Formula (1) as defined supra, and - one or more additional active ingredients, in particular one or more endo- and / or ectoparasiticides.
    [0075] [0075] The term "combination" in the present invention is used as known to those skilled in the art, and it is possible that said combination is a fixed combination, a non-fixed combination or a kit-of-parts.
    [0076] [0076] A "fixed combination" in the present invention is used as known to those skilled in the art. The fixed composition is, for example, a combination in which one or more compounds represented by Formula (1) of the present invention, and one or more additional active ingredients are present together in a unit dosage or in a single entity. An example of a “fixed combination” is a pharmaceutical composition in which a compound represented by the Formula
    [0077] [0077] A non-fixed combination or "kit-of-parts" in the present invention is used as known to those skilled in the art. The non-fixed combination is, for example, a combination in which one or more compounds represented by Formula (1) and one or more additional active ingredients are present in more than one unit. An example of a non-fixed combination or kit of parts is a combination in which a compound represented by Formula (1) and an additional active ingredient are present separately. The components of the non-fixed combination or kit-of-parts can be administered separately, sequentially, simultaneously, concomitantly or chronologically intercalated.
    [0078] [0078] The compound represented by Formula (1) can be administered as the sole pharmaceutical agent or in combination with one or more other pharmaceutically active ingredients, where the combination does not cause unacceptable adverse effects. The present invention also encompasses such pharmaceutical combinations. For example, the compound represented by Formula (1) can be combined with known ectoparasiticides and / or endoparasiticides.
    [0079] [0079] The other or additional active ingredients specified in this specification by their common names are known and described, for example, in “Pesticide
    [0080] [0080] Examples of insecticides, acaricides and nematicides, including ectoparasiticides and / or endoparasiticides, which can be used in the present invention include the following chemicals, without limitation: (1) Acetylcholinasterase (AChE) inhibitors, for example, carbamates, for example example, alanicarb, Aldicarb, Bendiocarb, Benfuracarbe, Butocarboxim, Butoxicarboxim, Carbaril, Carbofurano, Carbossulfano, Etiofencarbe, Fenobucarb, formetanato, Furatiocarb, Isoprocarb, Metiocarb, metomil, Metolcaroxia, tyrofox, tetrahydrate, pirofox, tetrahydrofluoride XMC and xylylcarb or organophosphates, for example, acephate, azametiphos, azinfos-ethyl, azinfos-methyl, Cadusafos, chloretoxifos, chlorfenvinfos, chlormphos, chlorpyrifos, chlorpyrifos-methyl, kaphos, cyanophos, Demeton-S-metil, dyldon-d-dos, metho , dicrotofos, dimetoate, dimethylvinfos, disulfoton, EPN, Etion, etoprofos, fanfur, fenamifos, Fenitrotion, Fention, fostiazato, heptenofos, imiciafos, Isofenfos, Isoprop il O- (methoxyamino-phosphoryl salicylate, Isoxation, Malation, Mecarbam, Metamidophos, Metidation, Mevinfos, Monocrotofos, Naled, Ometoate, oxidemeton-methyl, Paration, Paration-methyl, Fentoate,
    [0081] [0081] (2) Chloride channel blockers controlled by GABA, for example, cyclodiene organochlorines, for example, Chlordane and Endosulfan or phenylpyrazoles (fiproles), for example, Ethiprole and Fipronil.
    [0082] [0082] (3) Modulators of the sodium channel, for example pyrethroids, for example, Acrinatrine, Alethrin, d-cis-trans Alethrin, d-trans Alethrin, Bifenthrin, Bioalethrin, Bioalethrin isomer S-cyclopentenyl, Biormethrin, Cycloprotin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta- Cypermethrin, Cyphenothrin [isomer (1R) -trans] ) - (1R)), Esfenvalerate, Etofenprox, Fenpropatrina, Fenvalerato, Flucitrinato, Flumetrina, tau-Fluvalinato, Halfenprox, Imiprotrina, cadetrina, Permethrin, Pethetrine, Pyrethrin, Pyrethrin (Pyrethrin), Pyrethrin, Pyrethrin (Pyrethrin) , Teflutrin, Tetramethrin, Tetramethrin [isomer (1R)] Tralometrine and Transflutrin or DDT or Methoxychlor.
    [0083] [0083] (4) Competitive modulators of the nicotinic acetylcholine receptor (NAChRR), for example, neonicotinoids, for example, Acetamiprid, Clotianidin, Dinotefuran, Imidacloprid, Nitenpiram, Tiacloprida and Thiamethoxam or Nicotine or Sulfoxifurone or flupoxuron or flupoxuron or flupoxafurone or flupoxuron or flupoxydron or flupoxyuron or flupoxydron or flupoxydron.
    [0084] [0084] (5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChDR), for example, spinosyns, for example, Spinetoram and Spinosad.
    [0085] [0085] (6) Allosteric modulators controlled by chloride channel glutamate (GluCl), for example, avermectins / milbemycins, for example, Abamectin, emamectin benzoate, Lepimectin and Milbemectin.
    [0086] [0086] (7) Juvenile hormone mimetics, for example juvenile hormone analogs, for example, Hydroprene, Quinoprene and Methoprene or Fenoxycarb or Pyriproxyphene.
    [0087] [0087] (9) Cord organ modulators, for example, Pimetrozine or Flonicamid.
    [0088] [0088] (10) Mite growth inhibitors, for example, Clofentezine, Hexitiazox and Diflovidazine or Etoxazole.
    [0089] [0089] (12) ATP inhibitors, mitochondrial synthase, for example, ATP breakers, for example, diafentiuron or organotin compounds, for example, Azocyclotine, Cihexatin and Fembutatin or Propargite or Tetradifon oxide.
    [0090] [0090] (13) Decouplers of oxidative phosphorylation by breaking the proton gradient, for example, Clorfenapir, DNOC and Sulfluramide.
    [0091] [0091] (14) Nicotinic acetylcholine receptor channel blockers, for example, Bensultap, cartap hydrochloride, thiocyclam and thiossultap-sodium.
    [0092] [0092] (15) Chitin biosynthesis inhibitors, type O, for example, Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucicloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron and Triflubururon and Triflubururon and Triflubururon.
    [0093] [0093] (16) Chitin biosynthesis inhibitors, type 1,
    [0094] [0094] (17) Seed breaker (in particular for Diptera, ie dipterans) such as, for example, cyromazine.
    [0095] [0095] (18) Ecdysone receptor agonists, for example, Chromafenozide, Halofenozide, Methoxyfenozide and Tebufenozide.
    [0096] [0096] (19) Octopamine receptor agonists, For example, Amitraz.
    [0097] [0097] (20) Inhibitors of the mitochondrial electron transport of Complex III, for example, Hydramethylnon or Acequinocil or Fluacripyrima.
    [0098] [0098] (21) Inhibitors of the mitochondrial electron transport of Complex I, for example, METI group acaricides such as, for example, Phenazaquin, Fenpyroximate, Pyrimidifene, Pyridaben, Tebufenpirad and Tolfenpirad or Rotenone (Derris).
    [0099] [0099] (22) Voltage-dependent sodium channel blockers, for example, Indoxacarb or Metaflumizone.
    [0100] [0100] (23) Acetyl CoA carboxylase inhibitors, for example, derivatives of tetronic and tetramic acid, for example, spirodiclofen, spiromesifene and spirotetramat.
    [0101] [0101] (25) Inhibitors of complex II mitochondrial electron transport, for example, beta-ketonitrile derivatives, for example, Cienopyraphene and Cyflumetophen, and carboxanilides, for example, piflubumide.
    [0102] [0102] (28) Modulators of the ryanodine receptor, for example, diamides, for example, Chlorantraniliprol, Ciantraniliprol and Flubendiamide.
    [0103] [0103] Additional examples include: additional active ingredients such as, for example, Afidopiropeno, Afoxolaner,
    [0104] [0104] Additional EXAMPLES include: Additional active ingredients with unknown or non-specific mode of action, for example, fentrifanil phenoxacrim, cycloprene, chlorobenzylate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triaratene, clotiazoben, tetrasul, oleate , methoxyzazone, gossyplure, flutenzin, bromopropylate, cryolite; Active ingredients from other classes, for example, butacarb, dimethylan, cloetocarb, phosfocarb, pyrimiphos (- ethyl), paration (-ethyl), methacrifos, isopropyl o-salicylate, trichlorfon, sulprofos, propafos, sebufos, pyridation, protoate, diclofention demeton-S-methylsulfone, isazophos, cyanophenphs, dialiphos, carbofenotion, autathiophos, aromphenphenids (-methyl), azymphs (-ethyl), chlorpyrifos (-ethyl), fosmetilan, iodophenphos, dioxabenzophos, formotion, fonofos, phosphos, phosphos, phosphos, phosphos, phosphos, phosphos, phosphos, phosphos, phosphos, phosphos, phosphos; Organochlorines, for example, camfeclor, lindane, heptachlor; or phenylpyrazoles, for example, acetoprol, pirafluprol, pyriprol, vaniliprol, sisapronil; or isoxazolines, for example, sarolaner, afoxolaner, lotilaner,
    [0105] [0105] Additional examples include: Biologicals, hormones or pheromones, for example, natural products, for example, turingiensin, codlemone or neem components; Dinitrophenols, for example, dinocap, dinobuton, binapacril; Benzoylureas, for example, fluazuron, penfluron; Amidine derivatives, for example, clormebuform, cimiazole, demiditraz; and Bee hive varroa acaricides, for example, organic acids, for example, formic acid, oxalic acid.
    [0106] [0106] Preferred insecticides and acaricides for use in animal health include, without limitation: effectors in chloride channels controlled by arthropod binder, for example, chlordane, heptachlor, endoculfan,
    [0107] [0107] Exemplary “active ingredients from the endoparasiticide group as mixing partners include, without limitation, anthelmintic active compounds and active antiprotozoal compounds.
    [0108] [0108] Anthelmintic active compounds include, without limitation, the following nematicidal, trematicidal and / or cestocidal active compounds: of the macrocyclic lactone class, for example, eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin and milbemycin; from the class of benzimidazoles and probenzimidazoles, for example, oxybendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole and sulfendazole; from the class of depsipeptides, preferably cyclic depsipeptides, in particular 24-member cyclic depsipeptides, for example, emodepside and PF1022A; from the class of tetrahydropyrimidines, for example, morantel, pyrantel and oxantel; from the class of imidazothiazoles, for example, butamisole, levamisole, and tetramisole; from the class of aminophenylamidines, for example, amidantel, deacylated amidantel (dAMD) and tribendimidine; from the class of aminoacetonitriles, for example, monepantel; the class of paraherquamides, for example, paraherquamide and derquantel;
    [0109] [0109] Compounds - “active antiprotozoa include, without limitation, the following active compounds: of the class of triazines, for example, diclazuril, ponazuril, letrazuril and toltrazuril; of the polyether ionophore class, for example, monensin, salinomycin, maduramycin and narasin; the class of macrocyclic lactones, for example, milbemycin and erythromycin; the class of quinolones, for example, enrofloxacin and pradofloxacin;
    [0110] [0110] The compound represented by Formula (1) can also be used in vector control. For the purposes of the present invention, a vector is an arthropod, in particular an insect or arachnid, capable of transmitting pathogens such as, for example, viruses, worms, single-celled organisms and bacteria from a reservoir (plant, animal, human etc.) to a host. pathogens can be transmitted mechanically (eg, trachoma by non-biting flies) to a host, or by injection (eg, malaria parasites by mosquitoes) into a host.
    [0111] [0111] EXAMPLES of vectors and the diseases or pathogens they transmit are: 1) Mosquitoes - Anopheles: malaria, filariasis; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of other worms; - Aedes: yellow fever, dengue fever, filariasis, other viral diseases; - Simuliidae: transmission of worms, in particular Onchocerca volvulus; - Psychodidae: transmission of leishmaniasis 2) Lice: skin infections, epidemic typhus; 3) Fleas: pest, endemic typhus, cestodes; 4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterial diseases; 5) Mites: mites, epidemic typhus, vesicular rickettsiosis, tularemia, Saint Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo hemorrhagic fever, borreliosis; 6) Ticks: borreliosis such as Borrelia burgdorferi sensu lato, Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesiosis (Babesia canis canis), ehrlichiosis.
    [0112] [0112] Additional examples of vectors in the sense of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example, A. gambiae, A. arabiensis, A. funestus, A. dirus ( malaria) and Culex, psychodids such as Phlebotomus, Lutzomyia, lice, fleas, flies, mites and ticks capable of transmitting pathogens to animals and / or humans.
    [0113] [0113] Vector control is also possible if the compound represented by Formula (1) is a resistance breaker. The compound represented by Formula (1) is suitable for use in the prevention of diseases and / or pathogens transmitted by vectors. Thus, an additional aspect of the present invention is the use of a compound represented by Formula (1) for vector control in the field of animal health. Yet an additional aspect of the present invention is the use of a compound represented by Formula (1) for vector control in the field of human health.
    [0114] [0114] The compound represented by Formula (1) as an active ingredient can be used for the control of various pests that damage rice fields, fruit trees, vegetables, other crops and flowers and ornamental plants in agricultural, horticultural or stored grain products, Or sanitary pests. Examples of organisms that can be controlled by the compound represented by Formula (1) also include vermin, such as nematodes. In addition, the compound represented by Formula (1) has a strong insecticidal effect against Lepidoptera such as, for example, cottonworm (Diaphania indica), Oriental tea tortrix (Homona magnanima), cabbage moth (Hellulla undalis), Tortrix das summer fruits (Adoxophyes orana fasciata), minor tea tortrix (Adoxophyes “honmai), apple tortrix (Archips fuscocupreanus), peach fruit moth (Carposina niponensis), Manchurian fruit moth (Grapholita inopinata), fruit moth (Grapholita molesta), soybean borer (Leguminivora glycinivorella), mulberry caterpillar (Olethreutes mori),
    [0115] [0115] The compound represented by Formula (1) as an active ingredient has a remarkable insecticidal effect against the pests described above that damage various lowland crops, plateau crops, fruit trees, vegetables, other crops and vegetables. In this way, the insecticidal effect of the invention can be obtained by treating water from rice fields, stems and leaves of plants, or soil from lowland crops, plateaus, fruit trees, vegetables, other crops, and flowers and ornamental plants, during the seasons in which the appearance of these pests is expected, either before or at the point of appearance of the pest.
    [0116] [0116] According to one embodiment, a horticultural or agricultural insecticide containing the compound represented by Formula (1) as an active ingredient is provided. According to another embodiment, a method of protecting a crop from a harmful organism is provided, the method including treating a crop or soil for cultivation with an effective amount of the compound represented by Formula (1).
    [0117] [0117] According to one embodiment, a composition is provided that includes the compound represented by Formula (1) mixed with an inert carrier and, optionally, with an auxiliary agent. According to another embodiment, a mixture is provided that includes the compound represented by Formula (1) combined with at least one other insecticide and / or fungicide.
    [0118] [0118] The compound represented by Formula (1) is, in general, used in appropriate formulation forms according to use, prepared by conventional methods for the preparation of agricultural and horticultural chemicals. That is, the compound represented by Formula (1) can be used in suitable formulations, for example, a suspension, an emulsion, a liquid formulation, a water-dispersible powder, a granule, a powder formulation, a tablet Or the like, prepared by mixing the compound with at least one of a suitable inert carrier or an auxiliary agent, if necessary, in an appropriate proportion, followed by dissolution, separation, suspension, mixing, impregnation, adsorption or adhesion of the ingredients.
    [0119] [0119] The inert carrier that can be used in the invention can be a solid or a liquid, and examples of these include, in particular, soy powders, grain powders, wood powders, bark powders, coarse powders, powders tobacco, nutshell powders, bran, cellulose powders, plant extraction residues, synthetic polymers such as, for example,
    [0120] [0120] EXAMPLES of materials that can be used as an inert carrier in the form of a liquid include those that have the function as a solvent, as well as those that do not have the function as a solvent, but are still able to disperse the compound of the active ingredient with the help of an auxiliary agent. Examples of the inert carrier include: water, alcohols (e.g., methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone etc.), ethers (eg diethyl ether, dioxane, Celossolve, diisopropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg kerosene, mineral oil etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, alkyl naphthalene etc.), halogenated hydrocarbons (for example,
    [0121] [0121] EXAMPLES of the auxiliary agent include the following auxiliary agents, which are used alone or in combination of two or more of them, depending on the purpose; however, it is also possible to use no auxiliary agent.
    [0122] [0122] For the purposes of emulsification, dispersion, solubilization and / or wetting of the compound of the active ingredient, surfactants may be used. Examples of surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleates, alkyl aryl sulfonate, sulphonate sulfonate of lignin and higher esters of alcohol sulfonate.
    [0123] [0123] EXAMPLES of auxiliary agents that can be used for the purpose of stabilizing dispersion, adhesion and / or binding of the active ingredient compound include casein, gelatin, starch, methylcellulose, carboxymethylcellulose, arabic gum, polyvinyl alcohol, pine root oil , corn oil, bentonite, xanthan gum and lignin sulfonate salts.
    [0124] [0124] EXAMPLES of auxiliary agents that can be used to increase the fluidity of solid products include wax, salts of stearic acid and alkyl phosphoric esters. An auxiliary agent, such as a condensation product of naphthalene sulfonate or a condensed phosphate salt, can be used as a suspending agent in suspensions. An antifoam agent, such as silicone oils, can also be used as an auxiliary agent.
    [0125] [0125] In addition, the compound represented by Formula (1) is stable against light, heat, oxidation and the like but, if desired, more stable compositions can be obtained by adding a stabilizer. Examples of the stabilizer include antioxidants, UV absorbers, phenol derivatives such as BHT (2,6-di-t-butyl-4-methyl phenol), BHA (butylhydroxy anisol), bisphenol derivatives and aryl amines such as , for example, phenyl-a-naphthyl amine, phenyl-fB-naphthyl amine, condensation product of phenetidine and acetone, and benzophene compounds.
    [0126] [0126] The effective amount of the compound represented by Formula (1) is typically 0.5 to 20% by weight in a powder formulation, 5 to 50% by weight in an emulsion, 10 to 90% by weight in a dispersible powder in water, 0.1 to 20% by weight in a granule, and 10 to 90% by weight in a fluid formulation. Meanwhile, the amount of carrier in the respective formulations is typically 60 to 99% by weight in a powder formulation, 40 to 95% by weight in an emulsion, 10 to 90% by weight in a water dispersible powder, 80 to 99 % by weight in a granule and 10 to 90% by weight in a fluid formulation. The amount of auxiliary agent, such as those described above, is typically 0.1 to 20% by weight in a powder formulation, 1 to
    [0127] [0127] In order to control various pests, an amount of the compound represented by Formula (1) as an active ingredient that is effective for rust control can be applied, exactly as is, or as an appropriate dilution with water, or as a suspension, to crops in which the corresponding pests will appear or in places where such occurrence is not preferable. The amount of use depends on several factors, such as the purpose, the pest to be controlled, the growth state of the plant, the tendency of the pest to appear, the climate, the environmental conditions, the formulation, the method of use , place of use, time of use and the like. It is preferable to use the compound represented by Formula (1) as an active ingredient in the concentration of 0.0001 to 5000 ppm and, preferably, 0.01 to 1,000 ppm. The dose of the compound represented by Formula (1) that can be used in approximately 10 to (acre) is generally in the range of 1 to 300 g of the active ingredient.
    [0128] [0128] The compound represented by Formula (1) as an active ingredient can be used alone in the control of various pests in agricultural, horticultural and stored grain products, which damage rice fields, fruit trees, vegetables, other crops and flowers, or sanitary pests or nematodes. In addition, in order to obtain superior control effect with respect to the various pests that occur at the same time, the compound represented by Formula (1) can be used in combination with at least one other insecticide and / or fungicide.
    [0129] [0129] With respect to the mixed formulation (mixture) of the invention for the control of a pest, examples of an insecticide, an acaricide or a nematicide as a compound that can be combined with the compound represented by Formula (1) include a selected compound of a pyrethroid-based compound, an organophosphorus-based compound, an oxime-carbamate-based compound, a carbamate-based compound, a neonicotinoid-based compound, a diacylhydrazine-based compound, a compound based on benzoyl urea, a compound based on juvenile hormone, a compound based on organic cyclodiene chlorine, a compound based on 2-dimethylaminopropane-1,3-dithiol, an amidine based compound, a compound based on phenylpyrazole, a compound based on tin organ, a compound based on METI, a compound based on benzylate, a compound based on allyl-pyrrole, a compound based on dinitrophenol, a compound based on anthranil-diamide, a oxadiazine-based compound, a compound based on semicarbazone, a compound based on tetronic acid, a compound based on carbamoyl triazole, or a compound based on tetrazine. Examples of a fungicide that can be combined with the compound represented by Formula (1) include a strobilurin-based compound, an anilino-pyrimidine-based compound, an azole-based compound, an azole-based compound, a compound based on dithiocarbamate, a compound based on phenylcarbamate, a compound based on organic chlorine, a compound based on benzimidazole, a compound based on phenylamide, a compound based on sulfenic acid, a compound based on copper, a isoxazole-based compound, an organophosphorus-based compound, an N-halogenothioalkyl-based compound, a carboxyanilide-based compound, a morpholine-based compound, an organotin-based compound and a cyano-pyrrole. A fumigant such as, for example, chloropicrin or a natural product compound, for example, nicotine, can also be used in combination with the compound represented by Formula (1).
    [0130] [0130] EXAMPLES of compounds that can be used in combination with the compound represented by Formula (1) still include compounds other than the above groups. Specific examples include the following compounds: pyrethroid-based compounds and various isomers thereof, for example, acrinatrin, alethrin [isomer- (1R)] bifenthrin, bioallethrin, bioalethrin S-cyclopentenyl isomer, biormethrin, cycloprotrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, teta-cypermethrin, zeta-cypermethrin, cyphenothrin L (1R) -trans isomer], deltamethrin, empentrine [isomer- (EZ) - )], sphenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, imiprotrin, methotrine, metoflutrin, perchtrin, phenothrin [isomer- (1R) -trans], pretrethin, retrin, 55 silafluofen, teflutrin, tetramethrin, tetramethrin [isomer- (1R)], tralometrine, transflutrin, ZXI8901, biopermethrin, furamethrin, proflutrin, flubrocitrinate and dimeflutrin; organo-phosphorus-based compounds, for example, acephate, azametiphos, azinphos-methyl, azinphos-ethyl, cadusaphos, chlorethoxyphos, chlorfenvinfos, chlorephs, chlorpyrifos,
    [0131] [0131] When the compound represented by Formula (1) is used in combination with at least one other insecticide and / or fungicide, a mixed composition of the compound represented by Formula (1) and the other insecticide and / or fungicide can be used; alternatively, the compound represented by Formula (1) and the other insecticide / fungicide can be mixed and used at the time of application.
    [0132] [0132] With respect to a mixture of the compound represented by Formula (1) and another insecticide and / or fungicide, the mixing ratio of the compound represented by Formula (1) to the other insecticide and / or fungicide is, although not particularly limited , from 0.01: 100 to 100: 0.01, or from 0.1: 100 to 100: 0.1, or from 1: 100 to 100: 1, or from 1:10 to 10: 1, or l1 : 1 (all in terms of weight), when expressed as the compound of the invention: another insecticide and / or fungicide. In addition, any range obtained by replacing the upper limit or the lower limit of any of the above ranges with the upper limit or the lower limit of another range is also contemplated as a mixed ratio range in the present invention.
    [0133] [0133] IN addition to or in place of the aforementioned insecticide or fungicide, the compound represented by Formula (1 can be mixed with a plant protection agent, for example an herbicide, a fertilizer, a soil reformer, a control agent the growth of plants or any other material that is supposed to provide an additive effect or a synergistic effect, in order to form a multi-purpose composition that has high efficacy.
    [0134] [0134] According to another modality, a compound represented by the following Formula (2) is provided: Xs RF or CF3
    [0135] [0135] The compound represented by Formula (2) is also useful as an agent for the prolonged control of ectoparasites, or as a horticultural or agricultural insecticide, or for the protection of a crop from a harmful organism. Therefore, the compound represented by Formula (2) can similarly be used in compositions, mixtures,
    [0136] [0136] The compound represented by Formula (2) can be prepared with reference to methods known in the art; see, for example, WO 2005/073165, WO 2010/018714, WO 2011/093415, as well as WO 2010/013567 and WO 2010/018857. Exemplary synthetic methods will be detailed in Examples 1a59.
    [0137] [0137] The compound represented by Formula (2) is preferably selected from the group consisting of: N- (2-fluoro-3- ((2-iodo-4- (perfluoropropan-2-yl) -6- (tri fluoromethyl ) phenyl) carbamoyl) phenyl) -6- (tri-fluoromethyl) nicotinamide, N- (2-fluoro-3- ((2-iodo-4- (perfluoropropan-2-yl) -6- (tri-fluoromethyl) phenyl) carbamoyl ) phenyl) -N-methyl-6- (trifluoromethyl) nicotinamide, 6-fluoro-N- (2-fluoro-3- ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl ) carbamoyl) phenyl) nicotinamide, 6-fluoro-N- (2-fluoro-3- ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) carbamoyl) phenyl) -N- methylnicotinamide, 2-fluoro-3- (4-fluoro-N-methylbenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- ((trifluoromethyl) sulfonyl) phenyl) benzamide and 2-fluoro -3- (4-fluorobenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- ((trifluoromethyl) sulfonyl) phenyl) benzamide.
    [0138] [0138] The present invention can be further described in the following examples. However, these examples are not intended to limit the scope of this application.
    [0139] [0139] A 10-liter round-bottom flask, with four necks, equipped with an internal thermometer, a mechanical stirrer, a drip funnel, a pH controller (pH electrode) and a condenser were charged with 2-aminobenzotrifluoride ( 98.8%, 450.0 g, 2.760.6 mmol), tetrabutylammonium bromide (49.8 g, 154.6 mmol), ethyl acetate (2,250.0 g, 25.5 mol), perfluoro-2- iodopropane (1.24 kg, 4.14 mol) and water (900.0 g). Sodium hydrogen sulfite (89%, 334.2 q, 1.54 mol) in Na; aqueous CO3z 2.5% by weight (1.20 kg, 283.5 mmol) was added dropwise to the vigorously stirred solution in the bottle for 3 hours at 30ºC. During the addition of Na; sS; 0s aq., The pH value of the aqueous layer was adjusted to 4.4 + 0.1 using 18% of the aqueous NazCO3 weight. The resulting biphasic mixture was vigorously stirred for 3 hours at 30ºC. After the end of the reaction, the two transparent phases obtained were separated, and the organic layer was concentrated at 20 mmHg (2.6 kPa) (40ºC) to remove solvents. The resulting residue was washed with 5% by weight of Nas; CO; aqueous (1.76 kg, 828.2 mmol) at 90 ° C and water (1.62 kg) at 70 ° C, respectively, and a crude product was obtained as a yellow liquid. The crude product was vacuum distilled (3 mmHg (400 Pa)) at 100ºC, to generate 763.9 g of 4- (perfluoropropan-2-yl) -2- (trifluoromethyl) aniline as a yellow liquid (96.5% weight) (81.1% yield). Step 1-B: Preparation of 2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline
    [0140] [0140] A 3-liter round-bottomed flask with four necks equipped with a mechanical stirrer, a thermometer, a reflux condenser and a drip funnel (500 ml) was loaded with 4- (perfluoropropan-2-yl) -2 - (trifluoromethyl) aniline (as 100%; 340.0 g, 996.5 mmol) sulfuric acid (98% by weight, 19.9 g, 199.3 mmol) and methanol (1.020.0 gq). Iodine (99.5%, 151.8 g, 597.9 mmol) was added to the mixture at 20 ° C, and the resulting mixture was heated to 60 ° C. 50% aqueous ammonium peroxodisulfate (301.6 g, 647.7 mmol) was added dropwise to the solution over 0.5 hour at 60ºC. The resulting mixture was stirred at 60 ° C for 5 hours. After completion of the reaction, the excess amount of iodine was reduced to 10% by weight of Na7; SO0; aqueous (208.4 g, 165.3 mmol). Then, water (1,020.00 g) was added to the biphasic mixture. The two transparent phases were separated, and the organic layer was washed with 10% of the weight of NasCO; aqueous (105.6 g, 99.6 mmol) at 40ºC and 2.4% by weight of aqueous NaCl (697.0 g) at 40ºC, respectively, to obtain the crude product (95.4% by weight, 464, 4 g, 973.8 mmol) as a dark red liquid. Distillation under reduced pressure (2.5 mmHg (333.3 Pa)) generated 429.7 g of a fraction, mp 75- 76ºC (2.5 mmHg (333.3 Pa)), containing 97-98% of the weight 2- iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline (93.2% yield). Step 1-C: Preparation of 2-fluoro-3-nitrobenzoyl chloride
    [0141] [0141] A 10-liter, four-necked round-bottom flask equipped with an internal thermometer, a mechanical stirrer, a drip funnel and a reflux condenser was charged with 2-fluoro-3-nitrobenzoic acid (1,269 g, 6, 86 mol), N, N-dimethylformamide (20.5 g) and toluene (4450 g). The suspended mixture was heated to 75 ° C, and thionyl chloride (1227 g, 10.31 mol) was added dropwise at 80 ° C over 1 hour 55 min. The reaction mixture was stirred at 80ºC for 2 hours. After completion of the reaction, the solution was concentrated under reduced pressure at 40ºC. 2-fluoro-3-nitrobenzoyl chloride was obtained as a yellow oil (1,529 g), and was used for the next step without further purification. Step 1-D: Preparation of 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide
    [0142] [0142] A 10 liter round bottom flask equipped with a mechanical stirrer, a thermometer, a reflux condenser and a drip funnel was charged with 2-iodine-4- (perfluoropropan-2-yl) -6- (trifluoromethyl ) aniline (2,600 g, 5.71 mol), 1,3-dimethylimidazolidin-2-one (4,200 g) and diisopropylethylamine (1774 gq, 13.73 mol). 2-fluoro-3-nitrobenzoyl chloride (1,529 g) was added to the suspension at 20 ° C, and the resulting mixture was heated to 105 ° C, and stirred for 5 hours at that temperature. After cooling the reaction mixture to 20ºC, water (7800 g) and ethyl acetate (13.0 liters) were added. The resulting two layers were separated, and the organic layer was washed with 10% aqueous HCl (3,900 g) and saturated aqueous NaCl (4,000 9g), with saturated aqueous NaHCO3z (4,000 g) and saturated aqueous NaCl (4,000 g), and with Saturated aqueous NaCl (8,000 g) in succession, and then concentrated to generate a crude product (4,050 g). The crude product obtained was purified with column chromatography (silica gel: 12,000 g, eluent: ethyl acetate / n-hexane = 1/3, 70.0 liters). Diisopropyl ether (7.0 liters) and n-hexane (7.0 liters) were added to the purified product, and the resulting mixture was stirred overnight. After filtration, the obtained solid was washed with diisopropyl ether (3.5 liters) / n-hexane (3.5 liters), and dried under reduced pressure to generate 2-fluoro-N- (2-iodo-4- (perfluoropropan -2-1i1) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide (2,518 g, 70.8% yield). Step 1-E: Preparation of 3-amino-2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide
    [0143] [0143] A 20-liter, four-necked round-bottom flask equipped with an internal thermometer, a mechanical stirrer, a drip funnel and a reflux condenser was charged with 2-fluoro-N- (2-iodine-4- ( perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide (2,518 g, 4.05 mol), ethanol (9,950 g) and water (2,180 9). After heating to 50 ° C, concentrated HCl (16.9 g, 0.16 mol) was added dropwise to the suspension. Fe (565 g, 10.12 mol) was added in 11 portions (about 50 g each) at 60 ° C over 3 hours, and the reaction mixture was stirred at 65 ° C. After 3 hours, concentrated HCl (17.0 g, 0.1 l16 mol) was added additionally and the mixture was stirred at 65 ° C for 3 hours again. After cooling to 20ºC, the resulting mixture was filtered through a block of CELITEO, the filter cake was washed with ethanol (3.0 liters), and the filtrate was concentrated at 50ºC. The residue obtained was dissolved in ethyl acetate (5.0 liters) and washed with water (5.0 liters). The organic layer was dried with NasSOa (500 g) and concentrated at 40 ° C, to generate a crude product (2650 g). The crude product thus obtained was stirred with diisopropyl ether (2.7 liters) and n-hexane (2.7 liters) at room temperature for 4 hours. After filtration, the obtained solid was washed with diisopropyl ether / n-hexane = 1/1 (2.7 liters) and dried under reduced pressure to generate 3-amino-2-fluoro-N- (2-iodine-4- ( perfluoropropan-2-1i1) -6- (trifluoromethyl) phenyl) benzamide (2,268 g, 24.6% yield). Step 1-F: Preparation of 6- (trifluoromethyl) nicotinoyl chloride
    [0144] [0144] A 5-liter round bottom flask with four necks equipped with an internal thermometer, a mechanical stirrer, a drip funnel and a reflux condenser was charged with 6- (trifluoromethyl) nicotinic acid (782 g, 4.09 mol ), N, N-dimethylformamide (10.6 g) and toluene (2340 g). After heating the mixture to 80 ° C, thionyl chloride (878 g, 7.38 mol) was added dropwise over 1.5 hours. After stirring at 80ºC for 2 hours, the mixture was cooled to 40ºC and concentrated under reduced pressure at 50ºC, to generate 6- (trifluoromethyl) nicotinoyl chloride (786 g) as a yellow oil. The 6- (trifluoromethyl) nicotinoyl chloride obtained was used for the next step without further purification. Step 1-G: Preparation of N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) carbamoyl) phenyl) -6- (trifluoromethyl) nicotinamide (Compound 67)
    [0145] [0145] A 20-liter, four-necked round-bottom flask equipped with a mechanical stirrer, a thermometer,
    [0146] [0146] According to the method of Step 1-A of Example 1,4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) aniline was prepared from 2-trifluoromethoxyaniline. Step 2-B: Preparation of 2-bromo-4- (perfluoropropan-2-yl) - 6- (trifluoromethoxy) aniline
    [0147] [0147] N-Bromosuccinimide (4.33 g, 24.3 mmol) was added in portions to a solution in N, N-dimethylformamide (42 ml) of 4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) aniline (7.0 g, 20.3 mmol), and the resulting mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the mixture, and the resulting two layers were separated. The obtained organic layer was washed with saturated aqueous NaCl, dried with Na2SO4 and concentrated to generate a crude product. The crude product thus obtained was purified with column chromatography (silica gel, eluent: gradient of ethyl acetate / n-hexane = from 0/100 to 10/90) to generate 2-bromo-4- (perfluoropropan-2-yl ) -6- (trifluoromethoxy) aniline (5.6 g9, 65% yield) as an orange oil. Step 2-C: Preparation of 2-fluoro-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) -3-nitrobenzamide
    [0148] [0148] 2-Fluoro-3-nitrobenzoic acid (2.91 g 15.7 mmol was stirred with toluene (13 ml), and thionyl chloride (5.7 ml, 78.3 mmol) and N, N-dimethylformamide (2 drops) were added The resulting mixture was stirred at 90 ° C for 0.5 hour and concentrated to generate an acid chloride The acid chloride thus obtained was added to the mixture of 2-bromo-4-
    [0149] [0149] 2-Fluoro-N- (2-bromo-4- (perfluoropropan-2-i1) -6- (trifluoromethoxy) phenyl) -3-nitrobenzamide (4.9 gq, 8.3 mmol was dissolved in ethanol ( 39 ml), and SnCl7; (4.92 g, 25.9 mmol was added in portions under cooling. After concentrated HCl (5.35 g, 9.04 mmol) was added dropwise to the suspension, The resulting mixture was heated to 50 ° C. After 1.5 hours, the mixture was cooled to room temperature, and 10% aqueous NaOH (80 ml) was added. After filtration through a block of CELITEGS, the resulting filtrate was concentrated, dissolved in ethyl acetate and washed with water and aqueous saturated NaCl successively The organic layer was dried with NasSOas and concentrated to generate a crude product. The crude product thus obtained was purified with column chromatography (silica gel, eluent: acetate gradient). ethyl / n-heptane = from 20/80 to 25/75) to generate 3-amino-2-fluoro-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) benzamide like a red solid pale (4.8 g). Step 2-E: Preparation of N- (2-fluoro-3 - ((2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) carbamoyl) phenyl) -6- (trifluoromethyl) nicotinamide (Compound 99)
    [0150] [0150] 6- (Trifluoromethyl) nicotinic acid (100 mg) was stirred with toluene, and thionyl chloride (60 µl) and N, N-dimethylformamide (1 drops) were added to the mixture. The resulting mixture was stirred at 90 ° C for 2 hours and concentrated to generate an acid chloride. The acid chloride thus obtained was added to a tetrahydrofuran solution of 3-amino-2-fluoro-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) benzamide (300 mg) . Pyridine (100 µL) was added, and the resulting mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture, and the resulting two layers were separated. The organic layer was concentrated, and the crude product thus obtained was purified with column chromatography (silica gel, eluent: ethyl acetate / n-hexane) to generate N- (2-fluoro-3 - ((2-bromo-4 - (perfluoropropan-2-1i1) -6- (trifluoromethoxy) phenyl) carbamoyl) phenyl) -6- (trifluoromethyl) nicotinamide. Example 3: Preparation of N- (2-fluoro-3 - ((2-iodo-4-
    [0151] [0151] Sulfuric acid (0.87 g, 0.1 equivalent) and iodine (6.29 g, 24.8 mmol) were added to a solution in methanol (45 g) of 4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) aniline (15.0 g, 43.5 mmol), and the resulting mixture was heated to 60 ° C. 50.5% aqueous ammonium peroxodisulfate (6.43 g, 28.1 mmol) was added dropwise to the solution at 60ºC. After stirring at 60ºC for 4 hours, the resulting mixture was cooled to room temperature, and 10% by weight of NazSO0; aqueous (60 ml) was added. After stirring for 0.5 hour, n-hexane was added, and the resulting two transparent phases were separated. Then, the organic layer was washed with saturated aqueous NaCl and concentrated. The obtained crude product was purified with column chromatography (silica gel: eluent: n-hexane) to generate 2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) aniline as a yellow oil (13.5 qg, 65.8% yield). Step 3-C: Preparation of 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluomethoxy) phenyl) -3-nitrobenzamide
    [0152] [0152] 2-Fluoro-3-nitrobenzoic acid (5.4 g, 29.6 mmol was stirred with toluene (25 ml), and thionyl chloride (10.7 ml, 147 mmol) and N, N-dimethylformamide ( 2 drops) were added.The resulting mixture was stirred at 90 ° C for 0.5 hour and concentrated to generate an acid chloride The acid chloride thus obtained was added to the 2-iodine-4- suspension
    [0153] [0153] 2-Fluoro-N- (2-iodo-4- (perfluoropropan-2-1i1l1) -6- (trifluoromethoxy) phenyl) -3-nitrobenzamide (11.2 gq, 8.31 mmol was dissolved in ethanol ( 89 ml), and SnCl> (10.3 g, 54.4 mmol) was added in portions under cooling. After concentrated HCl (12.1 g, 18.9 mmol) was added dropwise to the suspension, the resulting mixture was heated to 50 ° C. After 1 hour, the mixture was cooled to room temperature, and 10% aqueous NaOH (80 ml) was added.After filtration through a block of CELITEGO, the filtrate was concentrated, dissolved in acetate and washed with water and saturated aqueous NaCl successively The organic layer was dried with Na-SOs and concentrated to generate a crude product. The crude product thus obtained was purified with column chromatography (silica gel, eluent: acetate gradient). ethyl / n-heptane = from 15/85 to 30/70), to generate 3-amino-2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) benzamide as a pale red solid ( 12 g). Step 3-E: Preparation of N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) carbamoyl) phenyl) -6- (trifluoromethyl) nicotinamide (Compound 118)
    [0154] [0154] According to the method of Step 2-E of Example 2, N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2-yl) -6- (tri fluoromethoxy) phenyl) carbamoyl) phenyl) -6- (trifluoromethyl) nicotinamide was prepared from 6- (trifluoromethyl) nicotinic acid and 3-amino-2-fluoro-N- (2-iodo- 4- (perfluoropropan-2-yl) - 6- (trifluoromethoxy) phenyl) benzamide. Example 4: Preparation of N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) carbamoyl) phenyl) -N-methyl-6- (trifluoromethyl ) nicotinamide (Compound 117) Step 4-A: Preparation of 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) -3- (methylamino) benzamide
    [0155] [0155] 3-Amino-2-fluoro-N- (2-iodo-4- (perfluoropropan-2- 11) -6- (trifluoromethoxy) phenyl) benzamide (4.0 g, 6.5 mmol) was dissolved in sulfuric acid (51 ml, 963 mmol), and formalin (10 ml) was added dropwise to the solution. During the addition, the temperature of the solution was controlled below
    [0156] [0156] According to the method of Step 2-E of Example 2, N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2-yl) -6- (tri fluoromethoxy) phenyl) carbamoyl) phenyl) -N-methyl-6- (trifluoromethyl) nicotinamide was prepared from 6- (tri-fluoromethyl) nicotinic acid and 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) - 6- (trifluoromethoxy) phenyl) -3- (methylamino) benzamide. Example 5: Preparation of N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) carbamoyl) phenyl) -N-methyl-6- (trifluoromethyl ) nicotinamide (Compound 66) Step 5-A: Preparation of 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (methylamino) benzamide
    [0157] [0157] According to the method of Step 4-A of Example 4, 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (methylamino ) benzamide was prepared from 3-amino-2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide.
    [0158] [0158] According to the method of Step 2-E of Example 2, N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2-yl) -6- (tri fluoromethyl) phenyl) carbamoyl) phenyl) -N-methyl-6- (trifluoromethyl) nicotinamide was prepared from 6- (tri-fluoromethyl) nicotinic acid and 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) - 6- (trifluoromethyl) phenyl) -3- (methylamino) benzamide.
    [0159] [0159] 6-Fluoricotinic acid (21.45 g) was stirred with toluene (115 ml), and thionyl chloride (27.7 ml, 380 mmol) and N, N-dimethylformamide (0.49 ml) were added to the mixture. The resulting mixture was stirred under reflux for 2 hours and concentrated, to generate an acid chloride. The acid chloride thus obtained was added to a tetrahydrofuran solution of 3-amino-2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide (75 gq, 127 mmol). Diisopropylethylamine (26.5 ml, 152 mmol) was added dropwise, and the resulting mixture was stirred at room temperature. Water and ethyl acetate were added to the reaction mixture, and the resulting two layers were separated. The organic layer was dried with Na7; SOs, concentrated, and the crude product thus obtained was washed with diisopropyl ether (500 ml 6 times 40ºC for 2 hours each), acetonitrile (400 ml, twice, 40ºC 1 hour each) and n -heptane (500 ml, 6 times, 40ºC each) to generate 6-
    [0160] [0160] According to the method of Step 2-E of Example 2, 6-fluoro-N- (2-fluoro-3- ((2-iodo-4- (perfluoropropan-2-1i1l) -6- (tri fluoromethyl) phenyl) carbamoyl) phenyl) -N-methylnicotinamide was prepared from 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (methylamino ) benzamide.
    [0161] [0161] According to the method of Step 1-A of Example 1,4- (perfluoropropan-2-yl) -2 - ((trifluoromethyl) thio) aniline was prepared from 2- ((trifluoromethyl) thio) aniline . Step 8-B: Preparation of 2-iodo-4- (perfluoropropan-2-yl) -6- ((trifluoromethyl) thio) aniline
    [0162] [0162] Sulfuric acid (8.99 ml, 169 mmol) and iodine (65.21 g, 514 mmol) were added to a solution in methanol (1,104 ml) of 4-— (perfluoropropan-2-yl) -2- ((trifluoromethyl) thio) aniline (290 g, 803 mmol), and the resulting mixture was heated to 60 ° C. 50% aqueous ammonium peroxodisulfate (119.09 g, 522 mmol) was added dropwise to the solution at 60ºC. After stirring at 60ºC for 2 hours, iodine (21.4 g, 169 mmol) and ammonium peroxodisulfate (17.29 g,
    [0163] [0163] A 2 liter round bottom flask equipped with a reflux condenser was charged with 2-fluoro-3-nitrobenzoic acid (118.76 g, 642 mmol) and toluene (656 ml). N, N-Dimethylformamide (20.5 g) and thionyl chloride (71.1 ml, 975 mmol) were added, and the resulting mixture was stirred at 90 ° C for 1.5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to generate an acid chloride.
    [0164] [0164] A 3-liter round bottom flask equipped with a mechanical stirrer, a thermometer and a reflux condenser was charged with 2-iodine-4- (perfluoropropan-2-yl) - 6- ((trifluoromethyl) thio) aniline (250 g, 513 mmol), 1,3-dimethylimidazolidin-2-one (365 ml) and diisopropylethylamine (215 ml, 1,232 mmol). A 1,3-dimethylimidazolidin-2-one solution of the above acid chloride was added at 27 ° C, the resulting mixture was heated to
    [0165] [0165] A 3-liter, four-necked round-bottom flask equipped with an internal thermometer, a mechanical stirrer and a reflux condenser was charged with 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-il ) -6- ((trifluoromethyl) thio) phenyl) -3-nitrobenzamide (265 q, 405 mmol), ethanol (1,419 ml), water (226 ml) and concentrated HCl (1,661 ml, 57.4 mmol). After heating to 60ºC, Fe (565 g, 10.12 mol) was added in portions and stirred for 1 hour. After cooling to room temperature, the resulting mixture was filtered through a block of CELITEO, and the filter cake was washed with ethyl acetate (1 liter, 4 times). After concentrating the filtrate at 40ºC, the residue obtained was dissolved in ethyl acetate (1.6 liter) and washed with water (1 liter) and saturated aqueous NaCl (1 liter) successively. The organic layer was dried with Na; SOs and concentrated, to generate a crude product. The crude product thus obtained was stirred with n-heptane at 40 ° C. After filtration, the obtained solid was washed with n-heptane and dried under reduced pressure to generate 3-amino-2-fluoro-N- (2-iodo- 4- (perfluoropropan-2-yl) -6- ((trifluoromethyl) thio) phenyl) benzamide (228 g, 295% yield). Step 8-E: Preparation of 2-fluoro-3- (4-fluorobenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6 - ((trifluoromethyl) thio) phenyl) benzamide
    [0166] [0166] 4-Fluorobenzoyl chloride (63.41 g, 0.4 mol) was added to a solution in tetrahydrofuran (2.41 liters) of 3-amino-2-fluoro-N- (2-iodo-4- (perfluoropropan-2- 11) -6- ((trifluoromethyl) thio) phenyl) benzamide (207.0 g, 0.333 mol). Pyridine (31.63 g) was added, and the resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, water (3.5 liters) and ethyl acetate (3.5 liters) were added to the reaction mixture, and the resulting two layers were separated. The organic layer was washed with 10% aqueous HCl (3.5 liters), NaHCO; saturated (3.5 liters) and saturated aqueous NaCl (3.5 liters) successively, dried with sodium sulfate and concentrated, to generate a crude product. The obtained crude product was washed with n-heptane / acetone and n-heptane successively, and dried under reduced pressure to generate 2-fluoro-3- (4-
    [0167] [0167] A 20-liter, four-necked round-bottom flask equipped with an internal thermometer and a mechanical stirrer was charged with 2-fluoro-3- (4-fluorobenzamido) - N- (2-iodine-4- ( perfluoropropan-2-yl) -6- ((trifluoromethyl) thio) phenyl) benzamide (163 g, 218 mmol), water (4,371 ml), acetonitrile (2,202 ml) and dichloromethane (2,192 ml), and then sodium periodate ( 214.89 g, 1,005 mmol) and RuCl3; (4.36 g, 65.3 mmol) was added. After stirring for 1 hour at room temperature, an aqueous solution (3 liters) of sodium thiosulfate (345.3 g, 2.184 mmol) was added, and the mixture was stirred for an additional 0.5 hour. The resulting mixture was extracted with ethyl acetate (3 liters, 4 times) and the combined organic layer was dried over sodium sulfate and concentrated, to generate a crude product. The crude product thus obtained was stirred with ethyl acetate (500 ml) for 2 hours. After filtration, the obtained solid was washed with ethyl acetate (100 ml) and dried under reduced pressure for 2 days to generate 2-fluoro-3- (4-fluoro-N-methylbenzamido) -N- (2-iodo-4 - (perfluoropropan-2-yl) -6- (((trifluoromethyl) sulfonyl) phenyl) benzamide (103 g, 132 mmol, 60.6% yield). Example 9: Preparation of 2-fluoro-3- (4-fluoro-N-methylbenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6-
    [0168] [0168] According to the method of Step 4-A of Example 4, 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- ((trifluoromethyl) thio) phenyl) -3 - (methylamino) benzamide was prepared from 3-amino-2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (((trifluoromethyl) thio) phenyl) benzamide Step 9-B : Preparation of 2-fluoro-3- (4-fluoro-N-methylbenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- ((trifluoromethyl) thio) phenyl) benzamide
    [0169] [0169] According to the method of Step 2-E of Example 2,2-fluoro-3- (4-fluoro-N-methylbenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) - 6- ((trifluoromethyl) thio) phenyl) benzamide was prepared from 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- ((trifluoromethyl) thio) phenyl) -3- (methylamino) benzamide.
    [0170] [0170] According to the method of Step 8-F of Example 8, 2-fluoro-3- (4-fluoro-N-methylbenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) - 6- ((trifluoromethyl) sulfonyl) phenyl) benzamide was prepared from 2-fluoro-3- (4-fluoro-N-methylbenzamido) -N- (2-iodo- 4- (perfluoropropan-2-yl) -6 - (((trifluoromethyl) thio) phenyl) benzamide.
    [0171] [0171] The compounds according to the invention shown in
    [0172] [0172] Compound (B) disclosed in WO 2010/018857, fluralaner and afoxolaner were used as comparative compounds in the following test examples.
    [0173] [0173] In vitro flea contact tests were performed with adult male and female cat fleas (Ctenocephalides felis).
    [0174] [0174] To coat the test tubes, the test substance was dissolved and diluted in acetone p.a. to the desired concentration. The solution was then applied homogeneously to the inner wall and base of a glass tube by rotating and shaking on an orbital shaker until the solvent had completely evaporated. For example, with a 900 ppm test substance solution, a dose based on an area of 5 µg / cm was gotten.
    [0175] [0175] Upon complete evaporation of the solvent, 5-10 adult cat fleas (Ctenocephalides felis) were added to each coated tube, which was then sealed with a perforated plastic cap and incubated in a horizontal position at room temperature and room humidity. After 48 h, the insecticidal activity against fleas was determined. For this, the fleas were collected up to the base of the tube by shaking the tube, and the tube was allowed to rest facing upwards. Fleas that remained motionless at the base or moved in an uncoordinated manner were considered dead or dying, respectively.
    [0176] [0176] A substance was considered to have good insecticidal activity against Ctenocephalides felis when at least 80% of the fleas were found dead or dying at a dose of the substance of 5 ug / cm . 100% insecticidal activity means that all fleas were found dead or dying. 0% insecticidal activity means that no fleas were found dead or dying.
    [0177] [0177] In this test, for example, the following compounds in the preparation examples exhibited 95% insecticidal activity at a dose of 1 µg / cm : Compounds 24, 26, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, 19, 20, 21, 29, 33, 38, 39, 23, 37, 44, 46, 47, 48, 49, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 17, 35, 34, 79, 66, 67, 81, 82, 75, 77, 78, 74, 73, 72, 71, 70, 64, 69, 65, 68, 63, 83, 85, 86, 87, 13, 88, 89, 90, 91, 92, 93, 36, 95, 97, 96, 101, 100, 98,
    [0178] [0178] In this test, for example, the following compounds from the preparation examples exhibited 95% insecticidal activity at a dose of 0.2 pug / cm : Compounds 24, 26, 3, 4, 5, 6, 8, 9, 10, 11, 12, 14, 15, 16, 19, 20, 21, 29, 33, 38, 23, 37, 44, 47, 49, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 17, 35, 34, 79, 66, 67, 81, 82, 75, 77, 78, 74, 73, 72, 71, 70, 64, 69, 65, 68, 83, 85, 86, 87, 13, 88, 89, 90, 91, 92, 93, 36, 95, 97, 96, 101, 100, 98, 102, 104, 103, 106, 105 107, 108, 109, 110 , 111, 115, 116, 117, 118 and 119.
    [0179] [0179] In this test, for example, the following compounds from the preparation examples exhibited 95% insecticidal activity at a dose of 0.04 µg / cm : Compounds 24, 26, 16, 21, 23, 37, 49, 51, 53, 54, 56, 57, 58, 17, 67, 81, 82, 74, 73, 83, 85, 86, 87, 89, 90, 91, 92, 93, 36, 97, 96, 101, 100, 104, 103, 106, 105, 107, 109, 111, 115, 116 and 119.
    [0180] [0180] In vitro contact tests with ticks were performed with adult males and females of Rhipicephalus sanguineus, Ixodes ricinus or Dermacentor variabilis, or nymphs of Amblyomma americanum.
    [0181] [0181] For the coating of the test flasks, the test substance was dissolved and diluted in acetone p.a. to the desired concentration. The solution was then applied homogeneously to the inner wall and bottom of a glass bottle by turning and shaking on an orbital shaker until the solvent had completely evaporated. For example, with a 900 ppm test substance solution, a dose based on an area of 5 µg / cm was gotten.
    [0182] [0182] After the solvent has completely evaporated, 5-10 adult ticks were placed in each coated test flask, which was then sealed with a perforated plastic cap and incubated in a horizontal position in the dark at room temperature and room humidity (Rhipicephalus sanguineus) or in a controlled climate cabinet (Ixodes ricinus, Dermacentor variabilis, Amblyomma americanum [21ºC, 85% relative humidity] l). The acaricidal activity against the respective species of tick was determined after 48 h. For this, the ticks were collected to the bottom of the test flask by gentle shaking, and the test flasks were then incubated in a hot plate at 45-50ºC for, at most, min. Ticks that remained immobile at the base of the test bottle or moved in an uncoordinated way without deliberately moving away to avoid the heat were considered dead or dying, respectively.
    [0183] [0183] A substance was considered to have good acaricidal activity against the respective tick species when at least 80% of the ticks were found dead or dying at a dose of the substance of 5 µg / cm . A 100% acaricidal activity means that all ticks were dead or dying. A 0% acaricidal activity means that none of the ticks were found dead or dying.
    [0184] [0184] In this test, for example, did the following compounds in the preparation examples exhibit a 90% acaricidal activity at a dose of 1 µg / cm against Amblyomma americanum: Compounds 24, 26, 1, 2, 3, 4, 9, 11, 12, 15, 16, 19, 21, 29, 33, 38, 39, 23, 37, 46, 51, 56, 57 , 58, 59, 60, 62, 35, 34,
    [0185] [0185] In this test, for example, did the following compounds from the preparation examples exhibit a 90% acaricidal activity at a dose of 0.2 µg / cm against Amblyomma americanum: Compounds 24 and 26, and Compounds 11, 12, 15, 16, 21, 29, 33 38, 39, 37, 46, 56, 58, 60, 35, 34, 79, 67, 81, 82, 78, 74, 73, 71, 64, 69, 65, 84, 85, 86, 87, 13, 91, 92, 94, 36, 95, 97, 96, 101, 100, 102, 104, 103, 106, 108, 110, 115, l16 and
    [0186] [0186] In this test, for example, did the following compounds from the preparation examples exhibit a 90% acaricidal activity at a dose of 0.04 µg / cm against Amblyomma americanum: Compounds 12, 56, 35, 86, 91, 95, 104, 106, 105 and 110.
    [0187] [0187] In this test, for example, did the following compounds from the preparation examples exhibit a 90% acaricidal activity at a dose of 1 µg / cm against Dermacentor variabilis: Compounds 26, 5, 9, 16, 21, 29, 33, 38, 23, 37, 44, 51, 53, 54, 56, 57, 60, 62, 17, 35, 34, 80, 79 , 66, 67, 81, 82, 76, 77, 78, 74, 73, 72, 71, 64, 68, 63, 84, 85, 86, 87, 13, 88, 89, 90, 91, 93, 94 , 36, 95, 97, 96, 101, 99, 100, 98, 102, 104, 103, 106, 105, 107, 108, 109, 110, 115 and 119.
    [0188] [0188] In this test, for example, did the following compounds in the preparation examples exhibit a 90% acaricidal activity at a dose of 0.2 pg / cm against Dermacentor variabilis: Compounds 26, 9, 16, 21, 29, 33, 23, 37, 44, 51, 53, 54, 56, 57, 17, 35, 34, 80, 67, 81, 82, 76, 77 , 78, 74,
    [0189] [0189] In this test, for example, did the following compounds from the preparation examples exhibit a 90% acaricidal activity at a dose of 0.04 upg / cm against Dermacentor variabilis: Compounds 23, 34, 81, 82, 78, 73, 85, 86, 91, 92, 97, 104, 103 and 106.
    [0190] [0190] In this test, for example, did the following compounds in the preparation examples exhibit a 90% acaricidal activity at a dose of 5 upg / cm against Ixodes ricinus: Compounds 24, 26, 9, 12, 16, 29, 35, 34, 80, 79, 67, 81, 82, 78, 74, 73, 72, 71, 64, 65, 68, 63, 84 , 85, 86, 13, 89, 90, 91, 92, 93, 36, 95, 97, 101, 102, 104, 103, 106, 105, 108, 109, 110, 115 and 118.
    [0191] [0191] In this test, for example, did the following compounds in the preparation examples exhibit a 90% acaricidal activity at a dose of 1 upg / cm against Ixodes ricinus: Compounds 24, 26, 9, 12, 16, 35, 34, 79, 67, 78, 74, 73, 72, 71, 64, 65, 68, 63, 84, 85, 86, 13, 89 , 90, 91, 92, 36, 95, 97, 96, 101, 99, 104, 106, 105, 108, 109, 110, 116 and 118.
    [0192] [0192] In this test, for example, did the following compounds in the preparation examples exhibit a 90% acaricidal activity at a dose of 0.2 pg / cm against Ixodes ricinus: Compounds 24, 9, 12, 16, 35, 67, 78, 73, 72, 71, 63, 84, 85, 86, 13, 89, 91, 92, 36, 95, 97, 101, 104 , 103, 106, 108, 109, 110, 116 and 118.
    [0193] [0193] In this test, for example, did the following compounds in the preparation examples exhibit a 90% acaricidal activity at a dose of 1 µg / cm against Rhipicephalus sanguineus: Compounds 24, 26, 3, 10, 11, 12, 14, 15, 16, 19, 21, 29, 39, 23, 37, 44, 51, 54, 57, 58, 59, 60, 62 , 17, 35, 34, 80, 79, 66, 67, 81, 82, 75, 76, 77, 78, 74, 73, 72, 71, 70, 64, 69, 65, 68, 63, 84, 85 , 86, 13, 88, 89, 90, 91, 92, 94, 36, 95, 97, 96, 101, 99, 100, 102, 104, 103, 106, 105 108, 110, 115, 116, 117 and 118.
    [0194] [0194] In this test, for example, did the following compounds in the preparation examples exhibit a 90% acaricidal activity at a dose of 0.2 upg / cm against Rhipicephalus sanguineus: Compounds 3, 9, 11, 12, 14, 15, 16, 19, 21, 29, 37, 44, 51, 54, 57, 59, 60, 17, 35, 34, 79, 66, 67 , 81, 82, 75, 76, 78, 74, 73, 72, 71, 70, 64, 69, 65, 68, 63, 84, 85, 86, 13, 88, 89, 90, 91, 92, 94 , 36, 95, 97, 101, 99, 102, 104, 103, 106, 107, 108, 110, 115, 117 and 118.
    [0195] [0195] In this test, for example, did the following compounds in the preparation examples exhibit a 90% acaricidal activity at a dose of 0.04 upg / cm against Rhipicephalus sanguineus: Compounds 11, 12, 16, 21, 29, 17, 35, 67, 82, 76, 74, 73, 72, 71, 68, 84, 86, 13, 91, 92, 36, 95, 104 , 106, 108, 109, and 115.
    [0196] [0196] To produce a mixture suitable for injection, the test substance was dissolved and diluted in dimethyl sulfoxide to the desired concentration. 1 pl of the test mixture was injected into the abdomen of each of 5 adult females engorged with cattle ticks (Rhipicephalus (Boophilus) microplus). Ticks were transferred to Petri dishes and kept in a room with controlled climate [28ºC, 85% relative humidity].
    [0197] [0197] The acaricidal activity against cattle ticks was evaluated after 7 days by evaluating fertile eggs laid. Eggs that did not look normal were stored in a controlled climate cabinet [28ºC, 85% relative humidity] until larval hatching after 42 days. A 100% acaricidal activity means that none of the ticks laid eggs or laid eggs that were infertile; 0% means that the ticks laid eggs, and all the eggs were fertile.
    [0198] [0198] In this test, for example, the following compounds in the preparation examples exhibited 100% acaricidal activity at a dose of 0.8 µg / animal: Compounds 24, 26, 1, 2, 3, 4, 5, 6 , 7, 9, 10, 11, 12, 14, 15, 16, 19, 20, 21, 32, 33, 38, 39, 40, 42, 23, 37, 44, 45, 46, 47, 48, 49 , 51, 52, 53, 54, 56, 57, 58, 59, 60, 61, 62, 17, 35, 34, 80, 79, 66, 67, 81, 82, 75, 76, 77, 78, 74 , 73, 72, 71, 70, 64, 69, 65, 68, 63, 83, 84, 85, 86, 87, 13, 88, 89, 90, 91, 92, 93, 94, 36, 95, 97 , 96, 101, 99, 100, 98, 102, 104, 103, 106, 105 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118 and 119.
    [0199] [0199] In this test, for example, the following compounds in the preparation examples exhibited 100% acaricidal activity at a dose of 0.16 pg / animal: Compounds 24, 26, 5, 9, 10, 11, 12, 14 , 15, 16, 19, 20, 21, 33, 38, 39, 42, 23, 37, 44, 45, 48, 49, 51, 53, 54, 56, 57, 58, 59, 60, 61, 62 , 17, 35, 34, 79, 66, 67, 81, 82, 75, 76, 77, 78, 74, 73, 72, 71, 70, 64, 69, 65, 68, 63, 83, 84, 85 , 86, 87, 13, 88, 89, 90, 91, 92, 93, 94, 36, 95, 97, 96, 101, 99, 100, 98, 102, 104, 103, 106, 105, 107, 108 , 109, 110, 111, 113, 115, 116, 117, 118 and 119.
    [0200] [0200] In this test, for example, the following compounds in the preparation examples exhibited 100% acaricidal activity at a dose of 0.032 µg / animal: Compounds 24, 26, 20, 21, 23, 37, 51, 54, 56 , 57, 58, 59, 60, 17, 35, 34, 79, 81, 82, 77, 78, 74, 73, 72, 71, 70, 64, 84, 85, 86, 87, 13, 88, 89 , 90, 91, 92, 93, 94, 36, 95, 96, 102, 104, 103, 106, 105, 107, 108, 109, 110, 113, 115, 116, 117, 118 and 119.
    [0201] [0201] In this test, for example, the following compounds from the preparation examples exhibited 100% acaricidal activity at a dose of 0.0064 µg / animal: Compounds 23, 37, 35, 34, 81, 82, 89, 90 , 92, 94, 104, 103, 106 and 109.
    [0202] [0202] To prepare a test blood mixture for flea feeding, the test substance was dissolved in dimethyl sulfoxide and diluted with cattle blood with citrate to the desired concentration.
    [0203] [0203] In order to set up the test configuration, about 20 non-fed adult male and female cat fleas (Ctenocephalides felis) were placed in a chamber that was closed at the top and bottom with gauze. A metal cylinder was sealed at one end with a parafilm membrane, placed with the base sealed in the chamber, and filled with the test blood mixture, which could be absorbed by the fleas through the parafilm membrane. The assembled test configuration was maintained at around 37ºC. After 48 hours, the insecticidal feeding activity against fleas was determined. 100% means that all fleas have been killed; 0% means that none of the fleas have been killed.
    [0204] [0204] In this test, for example, the following compounds in the preparation examples exhibited 95% insecticidal feeding activity at a dose of 4 ppm: Compounds 24, 26, 3, 5, 6, 7, 8, 9, 10 , 11, 12, 14, 15, 16, 19, 20, 21, 29, 32, 33, 38, 39, 40, 42, 18, 23, 37, 44, 45, 46, 47, 48, 49, 50 , 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 17, 35, 34, 80, 79, 66, 67, 81, 82, 75, 76, 77, 78 , 74, 73, 72, 71, 70, 64, 69, 65, 68, 63, 83, 84, 85, 86, 87, 13, 88, 89, 90, 91, 92, 93, 94, 36, 95 , 97, 96, 101, 99, 100, 98, 102, 104, 103, 106, 105, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118 and 119.
    [0205] [0205] In this test, for example, the following compounds in the preparation examples exhibited 95% insecticidal feeding activity at a dose of 0.8 ppm: Compounds 24, 26, 6, 8, 9, 11, 12, 14 , 16, 19, 20, 21, 29 33, 38, 39, 40, 42, 18, 23, 37, 44, 45, 46, 48, 49, 51, 53, 54, 56, 57, 58, 59, 60, 61, 62, 17, 35, 34, 80, 79, 66, 67, 81, 82, 75, 76, 77, 78, 74, 73, 72, 71, 70, 64, 69, 65, 68, 63, 83, 84, 85, 86, 87, 13, 88, 89, 90, 91, 92, 93, 94, 36, 95, 97, 96, 101, 99, 100, 98, 102, 104, 103, 106, 105, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118 and 119.
    [0206] [0206] In this test, for example, the following compounds in the preparation examples exhibited 95% insecticidal feeding activity at a dose of 0.16 ppm: Compounds 11, 14, 16, 33, 38, 23, 37, 44 , 45, 46, 48, 49 51, 53, 54, 56, 57, 59, 60, 62, 17, 35, 34, 80, 79, 66, 67, 81, 82, 77, 78, 74, 73, 70, 64, 69, 65, 68, 63, 83, 84, 85, 86, 87, 13, 88, 89, 90, 91, 92, 93, 94, 36, 95, 97, 96, 101, 99, 100, 102, 104, 103, 106, 105, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118 and 119.
    [0207] [0207] In this test, for example, the following compounds in the preparation examples exhibited 95% insecticidal feeding activity at a dose of 0.032 ppm: Compounds 16, 23, 37, 49, 51, 53, 54, 17, 35 , 34, 80, 74, 70, 69, 65, 68, 63, 83, 85, 86, 87, 13, 88, 89, 90, 91, 92, 93, 94, 102, 104, 103, 106, 105 , 107, 108, 109, 110, 111, 113, 115, 116, 117, 118 and 119.
    [0208] [0208] In this test, for example, the following compounds in the preparation examples exhibited 95% insecticidal feeding activity at a dose of 0.0064 ppm: Compounds 16, 23, 49, 51, 53, 17, 34, 85 , 36, 103, 106, 108, 111, 115, and 116.
    [0209] [0209] Study type and overall study design: The method is a randomized efficacy study not blinded according to the requirements of the “European Animal Welfare”. The rats (Rattus norvegicus) were randomized based on pre-treatment flea counts. The effectiveness of the treatment was determined by comparing the flea and tick counts of different treatment groups versus the placebo-treated control group. The experimental unit was the individual study animal.
    [0210] [0210] Method and route of administration: The compound was applied in a suitable solvent and carrier (more specifically, added to the following mixture: 33.3% by weight of propylene carbonate, 67.7% by weight of N-methylpyrrolidone, 0.1% by weight of BHA, 0.05% by weight of BHT) considering the individual body weight as a topical spot-on between the shoulder blades directly on the skin.
    [0211] [0211] Experimental infestation: On the day of treatment and weekly thereafter, 30 ticks (D. variabilis nymphs) were released on the back of each rat, and 30 fleas (C. felis) were released on the back of each rat 24 hours later.
    [0212] [0212] Tick and flea count: Rats were carefully examined and ticks and fleas were removed manually 48 h (t + 4 h) after tick infestation and 24 h after flea infestation. Live fleas and live engorged ticks adhered were counted. In non-evident cases, the state of engorgement was assessed by squeezing the tick on a filter paper to find traces of blood as a sign of engorgement. Table 247: Average geometric percentage reduction in live tick (Dermacentor variabilis) counts compared to untreated control rats.
    [0213] [0213] Study type and overall study design: The method is a randomized efficacy study not blinded according to the requirements of the “European Animal Welfare”. The rats (Rattus norvegicus) were randomized based on pre-treatment flea counts. The effectiveness of the treatment was determined by comparing the flea and tick counts of different treatment groups versus the placebo-treated control group. The experimental unit was the individual study animal. Method and route of administration: The compound was applied in a suitable solvent and carrier (more specifically, added to the formal glycerol; in the case of poorly soluble compounds, a solvent mixture with up to 25% by volume of N-methyl pyrrolidone can be used) . Considering individual body weight as an intraperitoneal injection.
    [0214] [0214] Experimental infestation: On the day of treatment and weekly thereafter, 30 ticks (D. variabilis nymphs) were released on the back of each rat, and fleas (C. felis) were released on the back of each rat 24 hours later evening.
    [0215] [0215] Tick and flea count: Rats were carefully examined and ticks and fleas were removed manually 48 h (t 4 h) after tick infestation and 24 h after flea infestation. Live fleas and live engorged ticks adhered were counted. In non-evident cases, the state of engorgement was assessed by squeezing the tick on a filter paper to find traces of blood as a sign of engorgement. Table 249: Average geometric percentage reduction in counts of live ticks (Dermacentor variabilis) compared with untreated control rats.
    [0216] [0216] Cabbage leaves were immersed in a liquid containing the test compound at a predetermined concentration for 30 seconds and air dried. The leaves were placed in a 7 cm polyethylene cup, and the second-stage larvae of the common caterpillar were left in it. The cup was placed in a room with a constant temperature of 25ºC, and the survival rate was investigated after 6 days. The test was carried out with two groups of 5 larvae per group. As a result, Compounds No. * 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65 , 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81,
    [0217] [0217] Cabbage leaves were immersed in a liquid containing the test compound at a predetermined concentration for 30 seconds and air dried. They were placed in a 7 cm polyethylene cup, and the larvae in the third stage of the crucifer moth were left in it. The cup was placed in a room with a constant temperature of 25ºC, and the survival rate was investigated after 6 days. The test was carried out with two groups of 5 larvae per group. As a result, Compounds No. 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116 , 117, 118 and 119 exhibited a pesticide rate of 70% or more at a concentration of 100 ppm.
    [0218] [0218] An additional test was carried out with 10 small brown dictiopharids by preparing an acetone solution of the diluted test compound to a predetermined concentration, spraying the solution on rice seedlings and air drying the rice seedlings.
    The medicine was all used as received.
    The rice seedlings were placed in a room with a constant temperature of 25ºC, and the survival rate was investigated after 6 days.
    The test was carried out using a group of 10 pests.
    As a result, Compounds Nos. 44, 47, 49, 51, 53, 54, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 113, 115, 116, 117, 118 and 119 exhibited a pesticide rate of 70% or more in one concentration of 100 ppm.
    权利要求:
    Claims (1)
    [1]
    1. Agent for the long-term control of ectoparasites for an animal, characterized by being represented by the following Formula (1): Xs neF o CF3
    N X5 Xo “cr, O" 0) om A and x where: each of A1i, A; and A; independently represents a nitrogen atom or a C-X1i group, provided that at least one of A; or A; represents a C-X1 group, and provided that, when A; represents a nitrogen atom, A; represents CX; and A, represents a nitrogen atom; A, represents a C-X1 group; Ri represents a hydrogen atom or a C1-Ca alkyl group; R2 represents a trifluoromethyl group or a pentafluorethyl group; X represents a halogen atom, a C1-Ca alkyl group, a C1-Ca haloalkyl group, a C1-Ca alkoxy group, a C1-Ca haloalkoxy , a C1i-Ca alkylthio group, a C1i-Ca haloalkylthio group, a C1i-C'a alkylsulfinyl group, a C1i-Ca haloalkylsulfinyl group, a C1i-C's alkylsulfonyl group, a C1-Ca haloalkylsulfonyl group, an aminosulfinyl group, an aminosulfinyl group, aminosulfonyl group, a sulfamoyl group, a nitro group or a cyano group;
    each X ;, independently represents a hydrogen atom, a halogen atom, a C1-Ca alkyl group, a C1-Ca haloalkyl group, a C1i-Ca alkoxyl group, a Ci-Ca haloalkoxy or a cyano group, provided that, when X and X; are attached to adjacent carbon atoms, X and X1, together with the carbon atoms, can form a five- or six-membered ring system that can be aromatic or non-aromatic, where the ring contains 0, 1, 2 or 3 heteroatoms, each independently selected from N, O and S as ring members; each of X ;, X3; and Xsa independently represents a hydrogen atom or a fluorine atom; Xs represents a chlorine atom, a bromine atom or an iodine atom; and Y represents a single bond, O, S, a sulfoxide group or a sulfonyl group.
    2. Agent for the prolonged control of ectoparasites, according to claim 1, characterized by the fact that: each of A; and the; independently represents a C-X1 group; A, represents a nitrogen atom or a C-X1i group; A, represents a C-Xi group; R1 represents a hydrogen atom or a C1-Ca alkyl group; R7 represents a trifluoromethyl group; XxX represents a halogen atom or a C1-Ca haloalkyl group; X1 represents a hydrogen atom; each of X; and X'a represents a fluorine atom;
    XxX; represents a hydrogen atom; Xs represents a bromine atom or an iodine atom; and Y represents a single bond or a sulfonyl group; o ”(The CF;
    N x x “Mer Os N. Xa
    R dm et x where:
    each of A:;, A; and the; independently represents a nitrogen atom or a C-X group: i, provided that at least one of A; Or the; represents a C-X group: i, and provided that, when A; z represents a nitrogen atom, A; represents C-X: and A, represents a nitrogen atom;
    As, represents a C-X1i group;
    R1 represents a hydrogen atom or a C1-1 alkyl group;
    R2 represents a trifluoromethyl group or a pentafluorethyl group;
    XxX represents a halogen atom, a C1i-Ca alkyl group, a C1i-Ca haloalkyl group, a C1i-Ca alkoxyl group, a C1-Ca haloalkoxy, a C1i-Ca alkylthio group, a C1i-Ca haloalkyl group, a group C1i-Ca alkylsulfinyl, a C1i-Ca haloalkylsulfinyl group, a C1i-Cs alkylsulfonyl group, a C1-Ca haloalkylsulfonyl group, an aminosulfinyl group, an aminosulfonyl group, a sulfamoyl group, a nitro group or a cyano group;
    each X, independently represents a hydrogen atom, a halogen atom, a C1-Ca alkyl group, a C1i-Ca haloalkyl group, a C1-Cs alkoxy group, a C1-Ca haloalkoxy or a cyano group, provided that, when X and X ;, are attached to adjacent carbon atoms, X and X1, together with the carbon atoms, can form a five or six membered ring system that can be aromatic or non-aromatic, where the ring contains 0, 1, 2 or 3 heteroatoms, each independently selected from N, O and S as members of the ring;
    each of X; 7, X3; and Xa independently represents a hydrogen atom or a fluorine atom;
    Xs represents a chlorine atom, a bromine atom or an iodine atom; and Y represents a single bond, O, S, a sulfoxide group or a sulfonyl group.
    7. Preparation, according to claim 6, characterized by the fact that the preparation is for oral use.
    8. Preparation according to claim 6, characterized by the fact that the preparation is for parenteral use.
    9. Preparation, according to claim 6, characterized by the fact that the preparation is for dermal use.
    10. Preparation according to any one of claims 6 to 9, characterized in that the preparation is a single dose preparation.
    11. Method for the prolonged control of an ectoparasite in an animal, characterized by understanding the systemic application of a compound represented by the Formula (following 1: Rr A 'CF3
    N xs x “NO Xa content of As 2h x in which: each of Ai, A; and A; independently represents a nitrogen atom or a C-X1i group, provided that at least one of A; or A; represents a group C-X1, and provided that, when A; represents a nitrogen atom, A; represents CX; and Az represents a nitrogen atom;
    As, represents a C-X1i group;
    R1 represents a hydrogen atom or a C1-Ca alkyl group;
    R2 represents a trifluoromethyl group or a pentafluorethyl group;
    X represents a halogen atom, a C1i-Ca alkyl group, a C1i-Ca haloalkyl group, a C1i-Ca alkoxyl group, a C1-C4a haloalkoxy, a C1i-Ca alkylthio group, a Ci-Ca haloalkyl group, a group C1i-Ca alkylsulfinyl, a C1-Ca haloalkylsulfinyl group, a C1i-Cs alkylsulfonyl group, a C1i-Ca haloalkylsulfonyl group, an aminosulfinyl group, an aminosulfonyl group, a sulfamoyl group, a nitro group or a cyano group;
    each Xi, independently represents a hydrogen atom, a halogen atom, a C1-Ca alkyl group, a C1i-Ca haloalkyl group, a C1-Cas alkoxy group, a C1-Ca haloalkoxy or a cyano group, provided that, when X and X; are attached to adjacent carbon atoms, X and X1, together with the carbon atoms, can form a five- or six-membered ring system that can be aromatic or non-aromatic, where the ring contains 0, 1, 2 or 3 heteroatoms, each independently selected from N, O and S as ring members;
    each of X; 7, X3; and Xa independently represents a hydrogen atom or a fluorine atom;
    Xs represents a chlorine atom, a bromine atom or an iodine atom; and
    Y represents a single bond, O, S, a sulfoxide group or a sulfonyl group.
    12. Use of a compound characterized by the fact that it is represented by the following Formula (1), for the preparation of a medicine for the prolonged control of an ectoparasite in an animal, in which the said medicine is applied systemically to said animal:
    Xs NF o 'CF3 and xs X2 “er, DO Xa o of SM in x where:
    each of Ai, A; and the; independently represents a nitrogen atom or a C-X1i group, provided that at least one of A; Or the; represents a C-X1 group, and provided that, when A; represents a nitrogen atom, A; represents C-X; and Az represents a nitrogen atom;
    A, represents a C-X1 group;
    Ri represents a hydrogen atom or a C1-Ca alkyl group;
    R2 represents a trifluoromethyl group or a pentafluorethyl group;
    X represents a halogen atom, a C1-Ca alkyl group, a C1-Ca haloalkyl group, a C1-Ca alkoxy group, a C1-Ca haloalkoxy, a C1i-Ca alkylthio group, a C1i-Ca haloalkylthio group, a group C1-C'a alkylsulfinyl, a C1i-Ca haloalkylsulfinyl group, a C1i-C's alkylsulfonyl group, a C1-Ca haloalkylsulfonyl group, an aminosulfinyl group, an aminosulfonyl group, a sulfamoyl group, a nitro group or a cyano group; each X ;, independently represents a hydrogen atom, a halogen atom, a C1-C's alkyl group, a C1-Ca haloalkyl group, a C1i-Ca alkoxyl group, a C1-Ca haloalkoxy or a cyano group, provided that, when X and X1: 1 are attached to adjacent carbon atoms, X and Xi, together with the carbon atoms, can form a five or six membered ring system that can be aromatic or non-aromatic, where the ring contains 0 , 1, 2 or 3 heteroatoms, each independently selected from N, O and S as members of the ring; each of X7, X; and X 'independently represents a hydrogen atom or a fluorine atom; Xs represents a chlorine atom, a bromine atom or an iodine atom; and Y represents a single bond, O, S, a sulfoxide group or a sulfonyl group.
    13. Horticultural or agricultural insecticide characterized by containing a compound represented by the following Formula (1) as an active ingredient: Xs x F o CF; and x X2 "er, Dá" 0) from SM Asçhe x where: each of A1i, A; and the; independently represents a nitrogen atom or a C-X1i group, provided that at least one of A; Or the; represents a C-X group: i, and provided that, when A; represents a nitrogen atom, A; represents C-X: and Az represents a nitrogen atom;
    As represents a C-X1i group;
    R1 represents a hydrogen atom or a C1-1 alkyl group;
    R2 represents a trifluoromethyl group or a pentafluorethyl group;
    X represents a halogen atom, a C1-Ca alkyl group, a C1-Ca haloalkyl group, a C1i-Ca alkoxy group, a C1-Ca haloalkoxy, a C1i-Ca alkylthio group, a Ci-Ca haloalkyl group, a group C1i-Ca alkylsulfinyl, a C1i-Ca haloalkylsulfinyl group, a C1i-C'a alkylsulfonyl group, a C1-Ca haloalkylsulfonyl group, an aminosulfinyl group, an aminosulfonyl group, a sulfamoyl group, a nitro group or a cyano group;
    each Xi independently represents a hydrogen atom, a halogen atom, a C1-Ca alkyl group, a C1i-Ca haloalkyl group, a C1i-Ca alkoxyl group, a C1-Ca haloalkoxy or a cyano group, provided that when X and X ;, are attached to adjacent carbon atoms, X and X1, together with the carbon atoms, can form a five or six-membered ring system that can be aromatic or non-aromatic, where the ring contains 0, 1 , 2 or 3 heteroatoms, each independently selected from N, O and S as members of the ring;
    each of X, 7, X; and Xa independently represents a hydrogen atom or a fluorine atom;
    Xs represents a chlorine atom, a bromine atom or an iodine atom; and
    Y represents a single bond, O, S, a sulfoxide group or a sulfonyl group.
    14. Method of protecting a crop from a harmful organism, the method characterized by treating a crop or soil for cultivation with an effective amount of a compound represented by the following Formula (1): xs RF o OD E CF ;
    N xs Xo “er, O“ (1) dm without x where: each of Ai, A; and the; independently represents a nitrogen atom or a C-X1i group, provided that at least one of A; Or the; represents a C-X1 group, and provided that, when A; represents a nitrogen atom, A; represents C-X; and Az represents a nitrogen atom; A, represents a C-X1 group; Ri represents a hydrogen atom or a C1-Ca alkyl group; R2 represents a trifluoromethyl group or a pentafluorethyl group; X represents a halogen atom, a C1-Ca alkyl group, a C1-Ca haloalkyl group, a C1i-Ca alkoxyl group, a C1-Ca haloalkoxy, a C1i-Ca alkylthio group, a C1-Ca haloalkylthio group, a group C1-C 'alkylsulfinyl, a C1-Ca haloalkylsulfinyl group, a C1-C's alkylsulfonyl group, a group
    C1-Ca haloalkylsulfonyl, an aminosulfinyl group, an aminosulfonyl group, a sulfamoyl group, a nitro group or a cyano group; each X ;, independently represents a hydrogen atom, a halogen atom, a C1-C's alkyl group, a C1-Ca haloalkyl group, a C1i-Ca alkoxyl group, a C1-Ca haloalkoxy or a cyano group, provided that, when X and X1: 1 are attached to adjacent carbon atoms, X and Xi, together with the carbon atoms, can form a five or six membered ring system that can be aromatic or non-aromatic, where the ring contains 0 , 1, 2 or 3 heteroatoms, each independently selected from N, O and S as members of the ring; each of X ,, X; and X 'independently represents a hydrogen atom or a fluorine atom; Xs represents a chlorine atom, a bromine atom or an iodine atom; and Y represents a single bond, O, S, a sulfoxide group or a sulfonyl group.
    15. Composition characterized by comprising a compound represented by the following Formula (1) mixed with an inert carrier and, optionally, with an auxiliary agent: Xs and CF3
    N x x “ep mM eh where: X each of A:;, A; and the; independently represents a nitrogen atom or a C-X group: i, provided that at least one of A; Or the; represents a C-X group: i, and provided that, when A; z represents a nitrogen atom, A; represents C-X: and A, represents a nitrogen atom;
    As, represents a C-X1i group;
    R1 represents a hydrogen atom or a C1-1 alkyl group;
    R2 represents a trifluoromethyl group or a pentafluorethyl group;
    XxX represents a halogen atom, a C1i-Ca alkyl group, a C1i-Ca haloalkyl group, a C1i-Ca alkoxyl group, a C1-Ca haloalkoxy, a C1i-Ca alkylthio group, a C1i-Ca haloalkyl group, a group C1i-Ca alkylsulfinyl, a C1i-Ca haloalkylsulfinyl group, a C1i-Cs alkylsulfonyl group, a C1-Ca haloalkylsulfonyl group, an aminosulfinyl group, an aminosulfonyl group, a sulfamoyl group, a nitro group or a cyano group;
    each X, independently represents a hydrogen atom, a halogen atom, a C1-Ca alkyl group, a C1i-Ca haloalkyl group, a C1-Cs alkoxy group, a C1-Ca haloalkoxy or a cyano group, provided that, when X and X ;, are attached to adjacent carbon atoms, X and X1, together with the carbon atoms, can form a five or six membered ring system that can be aromatic or non-aromatic, where the ring contains 0, 1, 2 or 3 heteroatoms, each independently selected from N, O and S as members of the ring;
    each of X; 7, X3; and Xa independently represents a hydrogen atom or a fluorine atom;
    Xs represents a chlorine atom, a bromine atom or an iodine atom; and Y represents a single bond, O, S, a sulfoxide group or a sulfonyl group.
    16. Mixture characterized by comprising a compound represented by the following Formula (1) combined with at least one other insecticide and / or fungicide: Xs (er CF3
    N xs x “Content dm eh XxX where: each of A: i, A; and the; independently represents a nitrogen atom or a C-X1i group, provided that at least one of A; Or the; represents a C-X1 group, and provided that, when A; represents a nitrogen atom, A; represents C-X; and Az represents a nitrogen atom; A, represents a C-X1 group; Ri represents a hydrogen atom or a C1-Ca alkyl group; R2 represents a trifluoromethyl group or a pentafluorethyl group; X represents a halogen atom, a C1-C4 alkyl group, a C1-Ca haloalkyl group, a C1i-Ca alkoxy group, a C1-Ca haloalkoxy, a C1i-Ca alkylthio group, a C1-Ca haloalkylthio group, a group C1-C 'alkylsulfinyl, a C1-Ca haloalkylsulfinyl group, a C1-C's alkylsulfonyl group, a group
    C1-Ca haloalkylsulfonyl, an aminosulfinyl group, an aminosulfonyl group, a sulfamoyl group, a nitro group or a cyano group; each X ;, independently represents a hydrogen atom, a halogen atom, a C1-C's alkyl group, a C1-Ca haloalkyl group, a C1i-Ca alkoxyl group, a C1-Ca haloalkoxy or a cyano group, provided that, when X and X1: 1 are attached to adjacent carbon atoms, X and Xi, together with the carbon atoms, can form a five or six membered ring system that can be aromatic or non-aromatic, where the ring contains 0 , 1, 2 or 3 heteroatoms, each independently selected from N, O and S as members of the ring; each of X7, X; and Xs independently represents a hydrogen atom or a fluorine atom; Xs represents a chlorine atom, a bromine atom or an iodine atom; and Y represents a single bond, O, S, a sulfoxide group or a sulfonyl group.
    17. Compound characterized by being represented by the following Formula (2): xs NF o CF;
    N F “cr O. Ng, * 2)
    s
    DS where: Ri represents a hydrogen atom or a C1-Ca alkyl group; R2 represents a trifluoromethyl group or a pentafluorethyl group; X represents a fluorine atom, a difluoromethyl group or a trifluoromethyl group; Xs represents a bromine atom or an iodine atom; A represents a nitrogen atom or a C-H group; and Y represents a single bond, O, S, a sulfoxide group or a sulfonyl group when A represents a nitrogen atom, and Y represents S, a sulfoxide group or a sulfonyl group when A represents a C-H group.
    18. A compound according to claim 17, characterized by the fact that the compound is selected from the group consisting of: N- (2-fluoro-3- ((2-iodo-4- (perfluoropropan-2-yl) - 6- (trifluoromethyl) phenyl) carbamoyl) phenyl) -6- (trifluoromethyl) nicotinamide, N- (2-fluoro-3- ((2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) carbamoyl) phenyl) -N-methyl-6- (trifluoromethyl) nicotinamide, 6-fluoro-N- (2-fluoro-3- ((2-iodo-4- (perfluoropropan-2- 11) -6- ( trifluoromethyl) phenyl) carbamoyl) phenyl) nicotinamide, 6-fluoro-N- (2-fluoro-3 - ((2-iodo-4- (perfluoropropan-2- i1) -6- (trifluoromethyl) phenyl) carbamoyl) phenyl) -N- methylnicotinamide, 2-fluoro-3- (4-fluoro-N-methylbenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- ((trifluoromethyl) sulfonyl) phenyl) benzamide, and 2-fluoro-3- (4-fluorobenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6-
    ((trifluoromethyl) sulfonyl) phenyl) benzamide.
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    法律状态:
    2021-11-23| B350| Update of information on the portal [chapter 15.35 patent gazette]|
    优先权:
    申请号 | 申请日 | 专利标题
    JP2017-179947|2017-09-20|
    JP2017179947|2017-09-20|
    PCT/JP2018/036162|WO2019059412A1|2017-09-20|2018-09-19|Prolonged ectoparasite-controlling agent for animal|
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