Antibacterial and antifungal composition
A novel fungicidal composition using a mixture of compounds (A) and (B) addresses the limitations of existing fungicides by enhancing biological activity and safety while reducing environmental impact, providing effective protection against plant pathogens.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- SYNGENTA CROP PROTECITON AG
- Filing Date
- 2021-12-01
- Publication Date
- 2026-04-22
AI Technical Summary
Existing fungicide compounds do not adequately meet the needs of agricultural practices in terms of crop resistance, activity against specific plant pathogens, and environmental impact, necessitating the development of novel compositions with superior biological properties and broader activity spectra.
A bactericidal and fungicidal composition comprising a mixture of components (A) and (B), where (A) is a compound of formula (I) and (B) is selected from various oxadiazole derivatives, with specific weight ratios, enhancing biological activity and safety profiles.
The composition provides effective protection against plant pathogenic fungi with improved biological activity, safety, and reduced environmental impact, offering a broader activity spectrum and longer-lasting residual activity.
Smart Images

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Abstract
Description
[Technical Field]
[0001] The present invention relates to a novel fungicidal and antifungal composition, its use in agriculture or horticulture to control diseases caused by plant pathogens such as plant pathogenic fungi, and a method for controlling diseases in useful plants. [Background technology]
[0002] For example, certain oxadiazole derivatives are known as insecticides and acaricides, as described in Chinese Patent No. 1927860. The use of substituted oxadiazoles for controlling plant pathogenic fungi is described in International Publication No. 2013 / 064079, European Patent No. 0276432, and International Publication No. 2015 / 185485.
[0003] Although many fungicide compounds and compositions belonging to various different chemical classifications have been developed / are under development for use as fungicides on useful plant crops, their crop resistance and activity against specific plant pathogens do not always meet the needs of agricultural practices in many respects. Therefore, there is a continuous need to find novel compounds and compositions with superior biological properties for use in controlling or preventing plant infections caused by plant pathogens. For example, compounds with greater biological activity, a favorable activity spectrum, an increased stability profile, improved physicochemical properties, or increased biodegradability. Or, compositions with a broader activity spectrum, improved crop resistance, synergistic interactions or enhancing properties, or compositions that exhibit a faster onset of action or have longer-lasting residual activity, or compositions that enable a reduction in the number of applications and / or application rates required for the effective control of plant pathogens, thereby enabling beneficial resistance management, reduced environmental impact, and reduced worker exposure.
[0004] Some of these requirements can be met by using compositions containing mixtures of different bactericidal compounds with different mechanisms of action (for example, by combining bactericides with different activity spectra). [Overview of the Initiative] [Means for solving the problem]
[0005] According to the present invention, a bactericidal and fungicidal composition is provided which contains a mixture of components (A) and (B) as active ingredients, Component (A) is the compound of formula (I): [ka] (In the formula, R 1 These are hydrogen, -C(=O)CH3 or -C(=O)CH2CH3, R 2 is methyl or isopropyl, and R 3 (It is hydrogen or fluorine.) or its salts, enantiomers, tautomers or N-oxides; and Component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl N-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl [Tyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,A compound selected from the group consisting of 4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or a salt thereof, enantiomer, tautomer, or N-oxide.
[0006] Generally, the weight ratio of component (A) to component (B) can be 100:1 to 1:100, preferably 50:1 to 1:50, more preferably 20:1 to 1:40, even more preferably 15:1 to 1:30, even more preferably 12:1 to 1:25, or 10:1 to 1:20, or 10:1 to 1:10, or 5:1 to 1:15, or 5:1 to 1:5, or 4:1 to 1:4, or 3:1 to 1:10, or 3:1 to 1:3, or 2:1 to 1:5, or 1:1.
[0007] Furthermore, the present invention provides a method for controlling or preventing plant pathogenic diseases, particularly plant pathogenic fungi, of useful plants or their reproductive materials, which includes applying the bactericidal composition according to the present invention to useful plants, their locations, or their reproductive materials. [Modes for carrying out the invention]
[0008] The benefits provided by certain fungicidal mixed compositions according to the present invention may include, in particular, advantageous levels of biological activity for protecting plants from fungal diseases, or superior properties for use as an active ingredient in pesticides (e.g., high biological activity, advantageous activity spectrum, increased safety profile, improved physicochemical properties, or increased biodegradability).
[0009] In one composition according to the present invention, component (A) is a compound of formula (Ia): [ka] (In the formula, R 1 (These are hydrogen, -C(=O)CH3, or -C(=O)CH2CH3.) Alternatively, it may be a salt, enantiomer, tautomer, or N-oxide thereof.
[0010] In another composition according to the present invention, component (A) is a compound of formula (I-b):
Chemical formula
[0011] Preferably, component (A) is a compound selected from compounds A.01, A.02, A.03, A.04, A.05, A.06 and A.07 defined in Table A below.
[0012]
Table 1
[0013] The presence of one or more asymmetric carbon atoms in component (B) means that the compound can occur in optical isomeric forms, i.e., enantiomeric or diastereomeric forms. Also, atropisomers can result from the restriction of rotation about a single bond. The present invention includes all of these possible isomeric forms (e.g., geometric isomers) of component (B), and mixtures thereof. The present invention also includes all possible tautomeric forms of component (B), and racemic compounds, i.e., mixtures of at least two enantiomers in a substantially 50:50 ratio.
[0014] In each case, component (B) according to the present invention is in free form, oxidized form as N-oxide, or salt form such as, for example, a salt form that can be used agriculturally.
[0015] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing aromatic heterocyclic compounds. These are described, for example, in the book “Heterocyclic N-oxides”, A. Albini and S. Pietra, CRC Press, Boca Raton 1991.
[0016] Component (B) is a compound selected from compounds B.01, B.02, B.03, B.04, B.05, B.06, B.07, B.08, B.09, B.10, B.11, B.12, B.13, B.14, and B.15, as defined in Table B below.
[0017] [Table 2-1] [Table 2-2] [Table 2-3]
[0018] The presence of a chiral carbon atom in any of the compounds B.01, B.02, B.03, B.04, B.05, B.06, B.07, B.08, B.09, B.10, B.11, B.12, B.13, B.14, or B.15 as defined in Table B above means that these compounds can arise as chiral enantiomers, i.e., (R)- and (S)-enantiomers.
[0019] The enantiomerically pure final compound can be obtained from suitable racemic starting materials via standard physical separation techniques such as reversed-phase chiral chromatography, or by stereoselective synthesis techniques, for example, using chiral starting materials.
[0020] Preferred embodiments E.01 to E.105 listed in Table C below relate to binary mixtures, where the weight ratio of component (A) to component (B) may be 100:1 to 1:100, preferably 50:1 to 1:50, more preferably 20:1 to 1:40, even more preferably 15:1 to 1:30, even more preferably 12:1 to 1:25, or 10:1 to 1:20, or 10:1 to 1:10, or 5:1 to 1:15, or 5:1 to 1:5, or 4:1 to 1:4, or 3:1 to 1:10, or 3:1 to 1:3, or 2:1 to 1:5, or 1:1.
[0021] Table 3-1 Table 3-2
[0022] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.01), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 15:1 to 1:30.
[0023] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.02), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 15:1 to 1:30.
[0024] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.03), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 15:1 to 1:30.
[0025] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.04), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 15:1 to 1:30.
[0026] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.05), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 15:1 to 1:30.
[0027] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.06), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- Xadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(tri Fluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 15:1 to 1:30.
[0028] In a preferred composition according to the present invention, component (A) is [(1R,2R)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.07), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 15:1 to 1:30.
[0029] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.01), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 10:1 to 1:10.
[0030] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.02), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 10:1 to 1:10.
[0031] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.03), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 10:1 to 1:10.
[0032] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.04), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 10:1 to 1:10.
[0033] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.05), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 10:1 to 1:10.
[0034] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.06), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- Xadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(tri Fluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 10:1 to 1:10.
[0035] In a preferred composition according to the present invention, component (A) is [(1R,2R)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.07), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 10:1 to 1:10.
[0036] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.01), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 5:1 to 1:5.
[0037] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.02), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 5:1 to 1:5.
[0038] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.03), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 5:1 to 1:5.
[0039] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.04), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 5:1 to 1:5.
[0040] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.05), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 5:1 to 1:5.
[0041] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.06), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- Xadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(tri Fluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 5:1 to 1:5.
[0042] In a preferred composition according to the present invention, component (A) is [(1R,2R)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.07), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 5:1 to 1:5.
[0043] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.01), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 4:1 to 1:4.
[0044] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.02), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 4:1 to 1:4.
[0045] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.03), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 4:1 to 1:4.
[0046] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.04), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 4:1 to 1:4.
[0047] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.05), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 4:1 to 1:4.
[0048] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.06), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- Xadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(tri Fluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 4:1 to 1:4.
[0049] In a preferred composition according to the present invention, component (A) is [(1R,2R)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.07), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 4:1 to 1:4.
[0050] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.01), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 3:1 to 1:3.
[0051] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.02), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 3:1 to 1:3.
[0052] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.03), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 3:1 to 1:3.
[0053] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.04), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 3:1 to 1:3.
[0054] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.05), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 3:1 to 1:3.
[0055] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.06), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- Xadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(tri Fluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 3:1 to 1:3.
[0056] In a preferred composition according to the present invention, component (A) is [(1R,2R)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.07), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 3:1 to 1:3.
[0057] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.01), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 2:1 to 1:2.
[0058] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.02), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 2:1 to 1:2.
[0059] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.03), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 2:1 to 1:2.
[0060] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.04), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 2:1 to 1:2.
[0061] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.05), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 2:1 to 1:2.
[0062] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.06), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- Xadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(tri Fluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 2:1 to 1:2.
[0063] In a preferred composition according to the present invention, component (A) is [(1R,2R)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.07), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 2:1 to 1:2.
[0064] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.01), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 1:1.
[0065] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.02), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- [Il]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl) (Tyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 1:1.
[0066] In a preferred composition according to the present invention, component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.03), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 1:1.
[0067] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.04), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 1:1.
[0068] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate (A.05), or its salt, enantiomer, tautomer or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trif (Oxadiazole-3-yl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 1:1.
[0069] In a preferred composition according to the present invention, component (A) is [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.06), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- Xadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(tri Fluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 1:1.
[0070] In a preferred composition according to the present invention, component (A) is [(1R,2R)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (A.07), or its salt, enantiomer, tautomer, or N-oxide, and component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,Selected from the group consisting of 4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or their salts, enantiomers, tautomers, or N-oxides, where the weight ratio of component (A) to component (B) is 1:1.
[0071] In any of the compositions according to the present invention, the composition is an additional active ingredient, component (C), which is different from component (B), and is also methyltetrapol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metminostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, epoxyconazole, hexaconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidflumetofen, fluxapiroxad, sedaxane, bisphosphonate. Xaphene, Isopyrazam, Fluopyram, Fluindapir, Isoflucipram, Impilfluxam, Quinofumeline, Ipupurfenoquine, Aminopyriphene, Fluazinam, Fludioxonil, Fenpicoxamide, Florylpicoxamide, Fenpropidine, Fenpropimorph, Mancozeb, Chlorothalonil, Cyclobtriflam, Cu-Oxychloride, Cu-Hydroxide, N'-[5-Bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine), N'- [5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxyethoxy) Toxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(3-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N'-(2-bromo-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine,N'-[2-bromo-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-isopropyl-N-methyl-formamidine, N'-[4-(2-cyanophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-4-(2-methylphenoxy)phenyl]-N-ethyl-N-methyl-formamidine Zin, N-ethyl-N'-[4-(2-fluorophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-methyl-formamidine, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, 4-[[6-[2-(2,4-difluorophenyl)- 1,1-Difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazole-1-ylmethyl)cyclopentanecarboxylate, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol, 2-[6-(4-chlorophenyl Phenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzenecarbothioamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide,N-[N-Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, N-[(E)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]cyclopropanecarboxa It may contain a component (C) selected from the group consisting of mid, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethylisoquinoline, and 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethylisoquinoline.
[0072] Preferably, component (C), which is different from component (B), is methyltetrapol, azoxystrobin, trifloxystrobin, picoxystrobin, metminostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidflumetofen, sedaxane, isopyrazam, impilfluxam, fluazinam, florylpicoxamide, fenpropidine, mancozeb, chlorothalonil, cyclobutriflam, Cu-oxychloride, Cu-hydroxyl, N'-[5-bromo-2-methyl-6-( The compound is selected from the group consisting of 1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, and N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine.
[0073] Component (C) is referred to herein and above by the so-called "ISO common name" or other "common name" used in individual cases or trade names. Component (C) is publicly known, commercially available, and / or publicly known in the art in methods and / or literature (e.g., International Publication Nos. 2015 / 155075, 2016 / 202742, 2017 / 005710, 2018 / 108977, 2018 / 153707, 2018 / 098216, and 2019 It can be prepared using the methods reported in International Publications (e.g., / 093522, International Publication 2018 / 145921, International Publication 2015 / 185485, International Publication 2017 / 076742, International Publication 2017 / 081311, International Publication 2017 / 085100, International Publication 2017 / 093019, International Publication 2017 / 178245, and International Publication 2017 / 211649).
[0074] In embodiments of the present invention in which the composition comprises component (A), component (B), and component (C), the weight ratio of component (A) to the sum of component (B) and component (C) may be 100:1 to 1:100, preferably 50:1 to 1:50, more preferably 20:1 to 1:40, even more preferably 15:1 to 1:30, even more preferably 12:1 to 1:25, or 10:1 to 1:20, or 10:1 to 1:10, or 5:1 to 1:15, or 5:1 to 1:5, or 4:1 to 1:4, or 3:1 to 1:10, or 3:1 to 1:3, or 2:1 to 1:5, or 1:1.
[0075] Compounds of formula I can also be used as fungicides. The term "fungicide" as used herein means a compound that controls, denatures, or prevents the growth of fungi. The term "fungicide-effective amount" means an amount of such compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or denature effects include all deviations from natural development, such as death or delay, and prevention includes the formation of barriers or other defenses in plants to prevent fungal infection.
[0076] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
[0077] The term "plant reproductive material" refers to all reproductive parts of a plant, such as seeds, cuttings, or growing parts of a plant like tubers. This includes not only seeds in the strict sense, but also roots, fruits, tubers, bulbs, rhizomes, and other parts of the plant.
[0078] As used herein, the term “habitat” means a field where plants are growing, or where the seeds of cultivated plants are sown, or where seeds will be sown in the soil. This includes soil, seeds and seedlings, as well as established vegetation.
[0079] Throughout this specification, the term “composition” means various mixtures or combinations of components (A) and (B) (including the embodiments defined above), such as a single “pre-formulated” form, a composite spray mixture such as a “tank mixture” composed of individual formulations of a single active ingredient element, and a combination of a single active ingredient when applied sequentially (i.e., one after the other over a moderately short period of time, such as a few hours or a few days). The order in which components (A) and (B) are applied is not important for the function of the present invention.
[0080] The compositions of the present invention are effective against harmful microorganisms, such as those that cause plant pathogenic diseases, and are particularly effective against plant pathogenic fungi and bacteria.
[0081] The compositions of the present invention can be used to control plant diseases caused by a broad spectrum of fungal plant pathogens in the classification of Basidiomycete, Ascomycete, Oomycete and / or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and / or Mucoromycete.
[0082] The composition is effective in controlling a broad spectrum of plant diseases, including leaf pathogens of ornamental crops, turfgrass, vegetables, agricultural crops, cereals, and fruit crops.
[0083] These pathogens may include the following: The class Oomycete includes the following: Phytophthora diseases, such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora, and Phytophthora erythroseptica; Pythium aphanidermatum, Pythium arenomanes Pythium diseases, such as those caused by arrhenomanes, Pythium graminicola, Pythium irregulare, and Pythium ultimum; diseases caused by Peronosporales, such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo candida, Sclerophthora macrospora, and Bremia lactucae;Also, other species such as Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi, and Sclerospora graminicola. Ascomycetes, for example, Stemphylium solani, Stagonospora tainanensis, Spirocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola, Ophiobolus graminicola graminis), Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora, Apple scab fungus (Venturia inaequalis), Pyrenophora teres), wheat yellow spot disease fungus (Pyrenophora tritici-repentis), Alternaria alternata, Alternaria brassisicola (AlternariaPleosporales species such as brassicicola, Alternaria solani, and Alternaria tomatophila; Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Capnodiales species such as Cercosporella capsellae and Cercosporella herpotrichoides; Cladosporium carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, wheat leaf spot fungus (Mycosphaerella graminicola), Mycovellosiella coepkeii Magnaporthales species such as koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpotrichoides, Ramularia beticola, Ramularia collo-cygni, Gaeumannomyces graminis, Magnaporthe grisea, and Pyricularia oryzae (rice blast fungus); Anisogramma anomala, Apiognomonia errabunda, and Cytospora Platani), Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicolaDiaporthales species such as fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-juglandacearum, Tubakia dryina, a species of Dicarpera, and Valsa ceratosperma; as well as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, and Aspergillus fumigatus. fumigatus), Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, a species of Candida, Capnodium ramosum, a species of Cephaloascus, Cephalosporium gramineum, Ceratocystis paradoxa, a species of Chaetomium, Hymenoscyphus pseudoalbidus, a species of Coccidioides, Cylindrosporium padi padi), Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, a species of the genus EpidermophytonDiseases such as spot, leaf spot, blast, or canker and / or rot caused by other species including (spp.), Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans, etc.; Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca), Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, Monographella albescens, Monosporascus cannonballus, a species of Naemacyclus, Ophiostomanovo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, a species of Petriellidium spp.), species of the genus Pezicula, Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivoraomnivora), Physalospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, a species of the genus Scedosporium, Schizothyrium pomi pomi), Sclerotinia sclerotiorum, Sclerotinia minor; a species of the genus Sclerotium, Typhula ishikariensis, Seimatosporium mariae, Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis; for example, Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca fuligena, and apple powdery mildew (Podosphaera). Powdery mildew diseases such as those caused by Erysiphales, including *Erysiphales leucotricha*, *Podospaera macularis*, *Golovinomyces cichoracearum*, *Leveillula taurica*, *Microsphaera diffusa*, *Oidiopsis gossypii*, *Phyllactinia guttata*, and *Oidium arachidis*;For example, Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, and Phyllosticta cucurbitacearum. Fungi such as those caused by the Botryosphaeriales order (e.g., cucurbitacearum); anthracnose caused by the Glommerelales genus, such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum graminicola;In addition, for example, Acremonium strictum, Claviceps purpurea, Fusarium culmorum, Fusarium graminearum, Fusarium virguliforme, Fusarium oxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp.cubense, Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, and a species of the genus Gliocladium. Wilt or canker diseases caused by Hypocreales, such as Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium roseum, and Verticillium theobromae. Basidiomycete fungi, including those causing smut disease such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, and other species of the order Ustilaginales, such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, and Puccinia graminis. Puccinia graminis), Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp.Hordei, Puccinia striiformis f.sp.Pucciniales, including species such as Secalis, Pucciniastrum coryli, or Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor, and Uromyces vizie-fabie. Rust fungi such as those caused by the order Uredinales (viciae-fabae), as well as species of the genera Cryptococcus, Exobasidium vexans, Marasmiellus inoderma, Mycena, Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, and Waitea cylinata. Other rot and disease-causing fungi, such as those caused by *Tilletiia circinata*, *Rhizoctonia solani* (rice sheath blight), *Thanetephorus cucurmeris* (sugar beet root rot), *Entyloma dahliae*, *Entylomella microspora*, *Neovossia moliniae*, and *Tilletiia caries*. Blastocladiomycetes, such as Physoderma maydis. Mucoromycetes, including species of the genus Choanephora cucurbitarum, Mucor spp., and Rhizopus arrhizus. Furthermore, diseases caused by other species and genera closely related to those listed above.
[0084] In addition to its bactericidal activity, the composition may also have activity against bacteria and other related species such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, and Strptomyces scabies, as well as certain protozoa.
[0085] The compositions of the present invention include Ascomycetes (e.g., Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (e.g., Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); and Imperfect Fungi. imperfecti) (also known as Deuteromycetes; for example, Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia, and Pseudocercospora) It is particularly effective against plant pathogens belonging to the Oomycetes class (e.g., Phytophthora, Peronospora, Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).
[0086] Useful plant crops that can be used in the composition of the present invention are typically berries such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals such as barley, corn, millet, oats, rice, rye, sorghum, rye and wheat; fiber plants such as cotton, flax, hemp, jute and sisal; crops such as sugars and feed beets, coffee, hops, mustard, rapeseed (canola), poppies, sugarcane, sunflowers, tea and tobacco; fruit trees such as apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears and plums; and grasses such as Bermuda grass, strawberry grass, bentgrass, centipede grass, bog grass, ryegrass, American grass and Zoysia grass. Herbs; such as basil, borage, chives, coriander, lavender, lavage, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as kidney beans, lentils, peas, and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, pecans, pistachios, and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs, and trees; other trees such as cocoa, coconut, olive, and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, pumpkin, melon, okra, onions, pepper, potatoes, pumpkins, rhubarb, spinach, and tomatoes; and perennial and annual crops such as climbing plants such as grapes.
[0087] Crops are understood to be naturally occurring, obtained through conventional breeding methods, or obtained through genetic engineering. These include crops that possess so-called output traits (e.g., improved storage stability, higher nutritional value, and improved flavor).
[0088] Crops are understood to include crops that have been made resistant to herbicides such as bromoxynil or to certain types of herbicides such as ALS-, EPSPS-, GS-, HPPD-, and PPO- inhibitors. An example of a crop in which resistance to imidazolinones, such as imazamox, has been induced by conventional crossbreeding methods is Clearfield® summer canola. Examples of crops in which resistance to herbicides has been induced by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties, which are commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.
[0089] Crops should also be understood as having naturally occurring or acquired resistance to harmful insects. This includes plants transformed using recombinant DNA technology to possess, for example, the ability to synthesize one or more selectively acting toxins, such as those known to originate from toxin-producing bacteria. Examples of toxins that can be expressed include δ-endotoxin, vegetative insecticidal proteins (Vip), insecticidal proteins from nematode-symbiotic bacteria, and toxins produced by scorpions, arachnids, large wasps (wasp) and fungi.
[0090] An example of a crop modified to express Bacillus thuringiensis toxin is Bt maize KnockOut® (Syngenta Seeds). An example of a crop containing two or more genes encoding insecticidal resistance and therefore expressing two or more toxins is VipCot® (Syngenta Seeds). Crops or their seed materials can also be resistant to multiple pests (so-called superimposed transgenic events formed by genetic modification). For example, a plant can be herbicide resistant and express insecticidal proteins at the same time, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).
[0091] The fungicidal and antifungal composition according to the present invention can be used to control or prevent plant pathogenic diseases, particularly plant pathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants.
[0092] In particular, genetically modified soybean plants that express toxins such as insecticidal proteins like delta-endotoxin (e.g., Cry1Ac (Cry1Ac Bt protein)). Therefore, this includes Event MON87701 (U.S. Patent No. 8,049,071 and related applications and patents), and International Publication No. 2014 / 170327A1 (e.g., Intacta RR2 PRO TM See paragraph
[0008] relating to soybeans, which may include genetically modified soybean plants including event MON87751 (U.S. Patent Application Publication No. 2014 / 0373191) or event DAS-81419 (U.S. Patent No. 8632978 and related applications and patents).
[0093] Other genetically modified soybean plants have the following characteristics: Event SYHT0H2-HPPD resistance (U.S. Patent Application Publication No. 2014 / 0201860 and related applications and patents), Event MON89788-glyphosate resistance (U.S. Patent Application Publication No. 7,632,985 and related applications and patents), Event MON87708-dicamba resistance (U.S. Patent Application Publication No. 2011 / 0067134 and related applications and patents), Event DP- Event A2704-12-Glufosinate resistance (U.S. Patent Application Publication No. 2010 / 0184079 and related applications and patents), Event DP-305423-1-ALS resistance (U.S. Patent Application Publication No. 2008 / 0320616 and related applications and patents), Event A5547-1 Resistance to 27-glufosinate (see U.S. Patent Publication No. 2008 / 0196127 and related applications and patents), resistance to Event DAS-40278-9-2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see International Publication Nos. 2011 / 022469, 2011 / 022470, 2011 / 022471 and related applications and patents), resistance to Event 127-ALS (International Publication No. 2010 / 080829 and related applications and patents), may include resistance to event GTS40-3-2-glyphosate, resistance to event DAS-68416-4-2,4-dichlorophenoxyacetic acid and glufosinate, resistance to event FG72-glyphosate and isoxaflutol, resistance to event BPS-CV127-9-ALS and GU262-glufosinate, or resistance to event SYHT04R-HPPD.
[0094] The fungicidal composition of the present invention can be used to control or prevent plant pathogenic diseases, particularly plant pathogenic fungi (such as soybean rust (Phakopsora pachyrhizi)) in soybean plants. In particular, specific elite soybean plant varieties in which an R gene stack conferring a certain degree of immunity or resistance to specific soybean rust (Phakopsora pachyrhizi) has been gene-transplanted into the plant genome are known from scientific literature. See, for example, “Fighting Asian Soybean Rust”, Langenbach C, et al, Front Plant Science 7(797)2016).
[0095] Elite plants are plants from one of the elite lineages, and therefore, elite plants are representative plants from elite varieties. Non-exclusive examples of elite soybean varieties commercially available to farmers or soybean breeders include AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202, AG0934, AG1435, AG2031, AG2035, AG2433, AG2733, AG2933, AG3334, AG3832, AG4135, AG4632, AG4934, AG5831, AG6534, and AG7231 (Asgrow Seeds, Des Moines, Iowa, USA), BPR0144RR, BPR4077NRR, and BPR4390NRR (Bio Plant). Research, CampPoint, Ill., USA), DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, Ill., USA), DP4546RR and DP7870RR (Delta&Pine Land Company, Lubbock, Tex., USA), JG03R501, JG32R606C ADD, and JG55R503C (JGL Inc., Greencastle, Ind., USA), NKS13-K2 (NK Division of Syngenta Seeds, Golden Valley,Minnesota,USA), 90M01, 91M30, 92M33, 93M11, 94M30, 95M30, 97B52, P008T22R2, P16T1 7R2, P22T69R, P25T51R, P34T07R2, P35T58R, P39T67R, P47T36R, P46T21R, and P56T03R2 (Pioneer Hi-Bred International, Johnston, Iowa, USA), SG4771NRR and SG5161NRR / STS (Soygenetics, LLC, Lafayette, Ind.,USA), S00-K5, S11-L2, S28-Y2, S43-B1, S53-A1, S76-L9, S78-G6, S0009-M2, S007-Y4, S04-D3, S14-A6, S20-T6, S21-M7, S26-P3, S28-N6, S30-V6, S35-C3, S36-Y6, S39-C4, S47-K5, S48-D9, S52-Y2, S58-Z4, S67-R6, S73-S8, and S78-G6 (Syngenta Seeds, Henderson, Ky., USA), Richer (Northstar Seed Ltd.Alberta, CA), 14RD62 (Stine Seed Examples include Co.Ia., USA, or Armor4744 (Armor Seed, LLC, Ar., USA).
[0096] Therefore, in a more preferred embodiment, the fungicidal composition of the present invention is used to control soybean rust (Phakopsora pachyrhizi) (including its fungicide-resistant strains outlined below) in elite soybean plant varieties into which an R gene stack conferring some degree of immunity or resistance to a specific soybean rust (Phakopsora pachyrhizi) has been introduced into the plant genome. Such use can be expected to yield many advantages, such as improved biological activity, a favorable or broader activity spectrum (including susceptible and resistant strains of soybean rust (Phakopsora pachyrhizi)), improved safety profile, improved crop tolerance, synergistic interactions or enhancing properties, improved onset of action or longer-lasting residual activity, and plant pathogens (reduced application frequency and / or reduced application rate of compounds and compositions required for effective control of soybean rust (Phakopsora pachyrhizi), thereby enabling beneficial resistance management work, reduced environmental impact, and reduced worker exposure.
[0097] Under certain circumstances, when the fungicidal composition of the present invention is used to control or prevent plant pathogenic diseases, particularly plant pathogenic fungi (such as soybean rust (Phakopsora pachyrhizi)) in soybean plants (especially any of the genetically modified soybean plants mentioned above), synergistic interactions between the active ingredients may occur.
[0098] The bactericidal composition of the present invention can be used to control or prevent plant pathogenic diseases, particularly plant pathogenic fungi (especially soybean rust (Phakopsora pachyrhizi)) in soybean plants.
[0099] Furthermore, no cross-resistance has been observed to date between the components of (B) (including any one of compounds B.01 to B.15) and the current fungicides used to control Phakopsora pachyrhizi.
[0100] In fact, fungicide-resistant strains of soybean rust (Phakopsora pachyrhizi) have been reported in the scientific literature, and strains resistant to at least one fungicide from each of the following classifications of fungicide action modes have been observed: sterol demethylation inhibitors (DMIs), quinone-external inhibitors (QoIs), and succinate dehydrogenase inhibitors (SDHIs). For example, “Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding resistance mechanisms.”Schmitz HK et al,Pest Manag Sci (2014)70:378-388;“First detection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi”Simoes K et al,J Plant Dis Prot(2018)125:21-2;“Competitive fitness of Phakopsora pachyrhizi isolates with mutations in the CYP51 and CYTB genes.”Klosowski AC et al,Phytopathology(2016)106:1278-1284;“Detection of the F129L mutation in the cytochrome b gene in Phakopsora pachyrhizi.”Klosowski AC et al al,Pest Manag See Sci(2016)72:1211-1215.
[0101] Therefore, in preferred embodiments, the fungicidal composition of the present invention is used to control soybean rust (Phakopsora pachyrhizi) that is resistant to one or more fungicides from the following fungicidal MoA classifications: sterol demethylation inhibitors (DMIs), quinone-external inhibitors (QoIs), and succinate dehydrogenase inhibitors (SDHIs).
[0102] Component (A) used in accordance with the present invention can be formed according to any of the synthesis techniques described in International Publication No. 2019 / 173665.
[0103] Component (B) used in accordance with the present invention can be formed according to any of the synthesis techniques described in International Publication Nos. 2017 / 055469, 2017 / 055473, 2017 / 093348, 2017 / 118689, 2017 / 220485, 2018 / 065414, 2018 / 158365, 2018 / 177894, 2018 / 177880, 2018 / 219773, and 2019 / 002151.
[0104] When present in an aqueous medium, component (B) according to the present invention may exist in a reversible equilibrium with its corresponding covalent hydrate form. This dynamic equilibrium may be important for the biological activity of component (B).
[0105] Compositions of the present invention, including all embodiments and preferred examples thereof disclosed above, can also be mixed with one or more additional pesticides, such as further fungicides, insecticides, anthelmintics, fungicides, mite control agents, plant growth regulators, sterilizers, information chemicals, insecticides, attractants, pheromones, feeding stimulants, or other bioactive compounds, to form multi-component pesticides that provide an even broader spectrum of agricultural protection.
[0106] Examples of such agricultural protective agents that can be incorporated with the composition of the present invention are as follows: Etridiazole, Fluazinam, Benalaxyl, Benalaxyl-M (Kiraraxyl), Flalaxyl, Metalaxyl, Metalaxyl-M (Mephenoxam), Dodicine, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazole-2-yloxy)-2,5-dimethylphenyl]-N-ethyl-N-methyl-H Lummamidine, N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazole-5-yl]oxy]-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine, ethylimol, 3'-chloro-2-methoxy-N-[(3RS)-tetrahydro-2-oxofran-3-yl]aceto-2',6'-xylidide (clodilacon), cyprodinil, mepanipyrim, pi Rimetanil, Dithianone, Aureofungin, Blastocydin-S, Biphenyl, Chloroneb, Dichloran, Benzovindiflupyr, Pidiflumetofen, Hexachlorobenzene, Quintozene, Technazen, (TCNB), Torclophos-methyl, Metraphenone, 2,6-Dichloro-N-(4-trifluoromethylbenzyl)-Benzamide, Fluopicolide (Flupicolide), Thioximide, Flusulfamide, Benomyl, Carbendazim, Carbendazim Chlorhydrate, Chlorphenazole, Fuberidazole, Thiabendazole, Thiophanate-methyl, Benciavaricarb, Clobentiazon, Probenazole, Acibenzoral, Bethoxazine, Pyriophenone (IKF-309), Acibenzoral-S-methyl, Pyribencarb (KIF-7767), Butylamine, 3-Iodo-2-propynyl n-butylcarbamate (IPBC), iodocarb (isopropanylbutylcarbamate), isopropanylbutylcarbamate (iodocarb), picarbtrazox, polycarbamate, propamocarb, tolprocarb, 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-Tetramethyl-indan-4-yl)-1-methylpyrazole-4-carboxamide diclosimet, N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methylpyrazole-4-carboxamide Carpropamide, Chlorothalonil, Flumorph, Oxine-Copper, Cymoxanil, Phenamacryl, Cyazofamide, Fluthianil, Thiosiophen, Clozolinate, Iprodione, Procymidone, Vinclozoline, Bupirimate, Dinoctone, Dinopenton, Dinobutone, Dinocap, Meptyldinocap, Diphenylamine, Phosdiphen, 2,6-Dimethyl-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone, Azithiram, Etem, Ferbam, Mancozeb, Maneb, Metam, Methylam (Polyram), Methylam Mu-zinc, narbam, propineb, thyram, bepam (metham sodium), zineb, ziram, dithioether, isoprothiolane, etaboxam, fosetyl, fosetyl-Al, methyl bromide, methyl iodide, methyl isothiocyanate, cyclafram, fenflam, validamycin, streptomycin, (2RS)-2-bromo-2-(bromomethyl)glutaronitrile (bromotalonyl), dozin, doguazine, guazatin, iminoctadine, iminoctadine triacetate, 2,4-D, 2,4-DB, Kasugamycin, Dimethylmol, Fenhexamide, Himexazole, Hydroxyisoxazole, Imazalil, Imazalil sulfate, Oxypoconazole, Pefurazoate, Prochloraz, Triflumizole, Phenamidone, Bordeaux mixture, Calcium polysulfide, Copper acetate, Copper carbonate, Copper hydroxide, Copper naphthenate, Copper oleate, Copper oxychloride, Copper oxyquinolate, Copper silicate, Copper sulfate, Copper tolate, Cuprous oxide, Sulfur, Carbaryl, Phthalide, Dingjunezuo Qi), oxathiapiproline, fluoroimide, mandipropamide, KSF-1002, benzamorph, dimethomorph, fenpropimorph, tridemorph, dodemorph, diethofencarb, fentin acetate, fentin hydroxide, carboxyne, oxycarboxyne, dorazoxolone, famoxadone, m-phenylphenol, p-phenylphenol, tribromophenol (TBP), 2-[2-[(7,8-difluoro-2-methyl-3-quinol)oxy]-6-fluorophenyl]propan-2-ol 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinol)oxy]phenyl]propan-2-ol Cyflufenaamide, Ofrace, Oxadixyl, Flutolanil, Mepronil, Isofetamide, Fenpiclonil, Fludioxonil, Pencyclon, Edifenphos, Ipropenphos, Pyrazophos, Phosphate, Tecrophthalam, Captaphor, Captan, Ditalimphos, Triforine, Fenpropidine, Piperate Phosphorus, Ostol, 1-Methylcyclopropene, 4-CPA, Chlormecoat, Clofencet, Dichloroprop, Dimethipine, Endotar, Ethephon, Flumetraline, Forchlorfenuron, Gibberellic Acid, Gibberellin, Himexazole, Hydrazide Maleate, Mepicort, Naphthaleneacetamide, Paclobutrazol, Prohexadione, Prohexadione-Calcium, Thidiazuron, Tribuphos (Tributyl) Phosphotrithioate, Trinexapac, Uniconazole, α-Naphthaleneacetic acid, Polyoxin D (Polyoxyrim), BLAD, Chitosan, Phenoxanil, Holpet, 3-(Difluoromethyl)-N-Methoxy-1-methyl-N-[1-Methyl-2-(2,4,6-Trichlorophenyl)ethyl]pyrazole-4-carboxamide, Bixafen, Fluxapyroxad, Flamethopyr, Isopyrazam, Penflufen, Penthiopyrad, Sedaxane, Fenpyrazamine, Diclomazine, Pyriphenox, Boscalid, Fluopyram, Diflumetrim, Fenalimol, 5-Fluoro-2-(p-Tolylmethoxy)pyrimidine-4-amine Felimzone, dimethaclone, pyroquilon, proquinazide, ethoxyquin, quinoxyphene, 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline, 5-fluoro-3,3,4,4-tetramethyl-1-(3-quinolyl)isoquinoline, 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-Benzoxazepine, tebufloquine, oxolinic acid, quinomethionate (oxythioquinox, quinoxymethionate), spiroxamine, (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide, (mandestrobin), azoxystrobin, chemoxystrobin, dimoxystrobin, enestrobrin, enoxastrobin, phenamistrobin, fluphenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, methaminostrobin, metminostrobin, oryzastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, triclopyricarb, trifloxystrobin, amisulbrom, diclofluanide, trifluanide, buto-3-inyl N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, dazomet, isothianil, thiadinil, tifluzamide, benthazole (TCMTB), silthiofam, zoxamide, anirazine, tricyclazole, (.+-.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazole-1-yl)-cycloheptanol (huanjunzuo), 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazole-1-yl)propan-2-ol 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-Triazole-1-yl)-propan-2-ol (TCDP), Azaconazole, Vitertanol (Biroxazole), Bromuconazole, Crinbazole, Cyproconazole, Difenoconazole, Dimethoconazole, Diniconasol, Diniconasol-M, Epoxyconazole, Etaconazole, Fenbuconazole, Fluquinconazole, Flusilazole, Flutriahol, Hexaconazole, Imibe Penconazole, Ipconazole, Ipfentrifluconazole, Metoconazole, Mycrobutanil, Penconazole, Propiconazole, Prothioconazole, Simeconazole, Tebuconazole, Tetraconazole, Triadimefon, Triadimenol, Triazoxide, Triticonazole, Mefentrifluconazole, 2-[[(1R,5S)-5-[(4-fluorophenyl)methyl]-1-hydroxy-2 Fungicides such as 2-dimethylcyclopentylmethyl, 2-(2,4-difluorophenyl)oxiran-2-yl, 2-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl)methyl, ametoctrazine (imidium), iprofalicarb, valifenarate, 2-benzyl-4-chlorophenol (chlorophene), allyl alcohol, azaphenidine, benzalkonium chloride, chloropicrin, cresol, daracide, dichlorophene, diphenzocort, dipyrithione, N-(2-p-chlorobenzoylethyl)-hexaminonium chloride, NNF-0721, octylinone, oxasulfuron, propamidine, and propionic acid.
[0107] Abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinfos-methyl, bifenthrin, vinphenazate, buprofezin, carbofuran, cartap, chlorantraniliprole (DPX-E2Y45), chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyflumetofen, cyfluthrin, β-cyflumetofen Fluthrin, cyhalothrin, λ-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiurone, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, etiprol, phenothiocarb, phenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamide, flubendiamide, f Lucitrinate, τ-fluvalinate, fluphenelim (UR-50701), flufenoxuron, honofos, halophenozide, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, metofluthrin, monoclotophos, methoxyphenozide, nitenpyram, nithia Insecticides such as Zin, Novalon, Noviflumuron (XDE-007), Oxamyl, Parathion, Parathion-methyl, Permethrin, Phorate, Fosalon, Fosmet, Phosphamidone, Pyrimicarb, Profenofos, Profluthrin, Pymetrozine, Pyrafluprole, Pyrethrin, Pyridaryl, Pyrifluquinazon, Pyriprole, Pyriproxyfen, Rotenone, Ryanodine, Spinetram, Spinosad, Spirodiclofen, Spiromesifen (BSN 2060), Spirotetramat, Sulprofos, Tebufenozide, Teflubenzuron, Terftrin, Terbufos, Tetrachlorvinfos, Thiacloprid, Thiamethoxam, Thiodicarb, Thiosultap-sodium, Tralomethrin, Triazamate, Trichlorfon, and Triflumulon; Streptomycin and other disinfectants; Acaricides such as amitraz, quinomethionate, chlorobenzylate, cyenopyrafen, cyhexatine, dicofol, dienochlor, etoxazole, phenazaquin, fenbutasin oxide, fenpropasrin, fenpyroximate, hexythiazox, propargit, pyridaben, and tebufenpyrad; and Bacillus thuringiensis, Bacillus thuringiensis delta-endotoxin, baculovirus, and biological agents such as entomopathogenic bacteria, viruses, and fungi.
[0108] The above composition can be used in methods for controlling pests, which include applying a composition containing the above mixture to pests or their environment.
[0109] A mixture containing a compound of formula (B) selected from Table B (above) and one or more of the above-mentioned active ingredients can be applied in combination with a single active ingredient, for example, in a single "pre-formulated" form, as a composite spray mixture such as a "tank mixture" composed of individual formulations of a single active ingredient element, and when applied sequentially (i.e., one after the other over a moderately short period of time, such as a few hours or a few days). The order in which the compound of formula (B) selected from Table B (above) and the above-mentioned active ingredients are applied is not important for the function of the present invention.
[0110] The compositions of the present invention can also be used in crop fortification. In the present invention, “crop fortification” means improved plant vitality, improved plant quality, improved resistance to stressors, and / or improved input utilization efficiency.
[0111] In the present invention, "improvement of plant vitality" means that a specific trait is qualitatively or quantitatively improved when compared to the same trait in a control plant grown under the same conditions in which the method of the present invention does not exist. Such traits include, but are not limited to, earlier and / or improved germination, improved germination, ability to use fewer seeds, increased root growth, more developed root system, increased nodule formation, increased shoot growth, increased tillering, more vigorous tillering, more productive tillering, increased or improved plant uprightness, less plant verse (lodging), increased and / or improved plant height, increased plant weight (fresh or dry), larger leaf blades, greener leaf color, increased pigment content, increased photosynthetic activity, earlier flowering, longer spikes, earlier graining, increased seed, fruit, or pod size, increased number of pods or spikes, increased number of seeds per pod or spike, increased seed mass, enhanced seed filling, fewer basal leaves, delayed senescence, improved plant vitality, increased amino acid levels in storage tissues, and / or less input required (e.g., less fertilizer, water, and / or labor). Plants with improved vitality may have an increase in any of the aforementioned traits, or any combination or two or more of the aforementioned traits.
[0112] In the present invention, "improvement of plant quality" means that a specific trait is qualitatively or quantitatively improved when compared to the same trait in a control plant grown under the same conditions in which the method of the present invention does not exist. Such traits may include, but are not limited to, improved plant appearance, reduced ethylene (reduced production and / or suppression of sensitivity), improved quality of harvested products such as seeds, fruits, leaves, and vegetables (such improvements in quality may manifest as improved visual appearance of the harvested products), improved carbohydrate content (e.g., increased sugar and / or starch content, improved sugar-acid ratio, decreased reducing sugars, increased sugar production rate), improved protein content, improved oil content and composition, improved nutritional value, reduced anti-nutrient compounds, improved sensory characteristics (e.g., improved taste), and / or improved consumer health benefits (e.g., increased levels of vitamins and antioxidants), improved post-harvest characteristics (e.g., enhanced shelf life and / or storage stability, easier processability, easier compound extraction), more uniform crop development (e.g., synchronized germination, flowering, and / or fruiting of plants), and / or improved seed quality (e.g., for use in the next growing season). Plants with improved quality may have any of the aforementioned traits, or any combination of the aforementioned traits, or an increase in two or more of them.
[0113] In the present invention, “improved tolerance to stressors” means that a particular trait is qualitatively or quantitatively improved compared to the same trait in a control plant grown under the same conditions in which the method of the present invention is absent. Such traits include, but are not limited to, increased tolerance and / or resistance to abiotic stressors that cause suboptimal growth conditions such as drought (e.g., any stress that results in a lack of water in the plant, insufficient water uptake capacity, or reduced water supply to the plant), exposure to cold, heat, osmotic stress, UV stress, flooding, exposure to increased salinity (e.g., in the soil), increased minerals, ozone exposure, high light exposure, and / or limited availability of nutrients (e.g., nitrogen and / or phosphorus nutrients). Plants with improved tolerance to stressors may have an increase in any of the aforementioned traits, or any combination or two or more of the aforementioned traits. In the case of drought and nutrient stress, such improved tolerance may be due, for example, to more efficient uptake, use, or retention of water and nutrients.
[0114] In the present invention, "improved input utilization efficiency" means that a plant can grow more efficiently using a given input level compared to the growth of a control plant grown under the same conditions in which the method of the present invention does not exist. Specifically, inputs include, but are not limited to, fertilizers (such as nitrogen, phosphorus, potassium, and micronutrients), light, and water. A plant having improved input utilization efficiency may have improved use of any of the aforementioned inputs, or any combination of two or more of the aforementioned inputs.
[0115] Other crop enhancements of the present invention include reduced plant height or reduced tillering, which are beneficial features in crops or conditions where lower biomass and lower tillering are desirable.
[0116] Any or all of the above crop enhancements may result in improved yields by, for example, improving the physiological function of the plant, plant growth and development, and / or plant structure. In the context of the present invention, “yield” includes, but is not limited to, (i) increased biomass production, grain yield, starch content, oil content, and / or protein content, which may result from (a) an increase in the amount produced by the plant itself, or (b) an improved ability to harvest the plant body; (ii) improved harvest composition (e.g., improved sugar-acid ratio, improved oil composition, increased nutritional value, decreased anti-nutrient compounds, increased consumer health benefits); and / or (iii) an increased / enhanced ability to harvest the crop, improved crop processability, and / or better storage stability / shelf life. Increased yield of agricultural plants means that, where quantitative measurement is possible, the yield of the produce of each plant is increased by a measurable amount compared to the yield of the same produce of a plant produced under the same conditions but without applying the present invention. According to the present invention, it is preferable that the yield increases by at least 0.5%, more preferably at least 1%, even more preferably at least 2%, even more preferably at least 4%, preferably 5%, or more.
[0117] Any or all of the above crop enhancements may result in improved land use. That is, land that was previously unusable or not optimally suited for cultivation may become available. For example, plants that show an increased ability to survive in drought conditions may become cultivated in areas with insufficient rainfall, such as the outskirts or even the desert itself.
[0118] In one embodiment of the present invention, crop strengthening is achieved in a state where there is substantially no pressure from pests and / or diseases and / or abiotic stress. According to a further embodiment of the present invention, improvement of plant vitality, stress tolerance, quality and / or yield is achieved in a state where there is substantially no pressure from pests and / or diseases. For example, pests and / or diseases can be controlled by insecticidal treatment applied before or simultaneously with the method of the present invention. In yet another embodiment of the present invention, improvement of plant vitality, stress tolerance, quality and / or yield is achieved in a state where there is no pressure from pests and / or diseases. In a further embodiment, improvement of plant vitality, quality and / or yield is achieved in a state where there is no or substantially no abiotic stress.
[0119] The compositions of the present invention may be used in the field of protecting stored goods from fungal attacks. In the present invention, the term “stored goods” is understood to mean natural substances of plant and / or animal origin, as well as processed forms thereof, for which long-term protection derived from the natural life cycle is desired. Plant-derived stored goods, such as plants or parts thereof (e.g., stems, leaves, tubers, seeds, fruits, or grains), can be protected in their freshly harvested state or in processed forms such as pre-dried, humidified, crushed, ground, pressurized, or roasted. The definition of stored goods also includes wood in the form of unprocessed wood (e.g., building timber, power transmission towers, and fences) and wood in the form of finished products (e.g., furniture or wood products). Animal-derived stored goods include leather, leather products, furs, and hair. The compositions of the present invention can prevent adverse effects such as decay, discoloration, or mold growth. Preferably, “storage” is understood to mean natural substances of plant origin and / or processed forms thereof, and more preferably, fruits and processed forms thereof (such as pome fruits, drupes, muscovados, and citrus fruits, and processed forms thereof). In another preferred embodiment of the present invention, “storage” is understood to mean wood.
[0120] Therefore, a further aspect of the present invention is a method for protecting stored goods, which includes applying the composition of the present invention to the stored goods.
[0121] The compositions of the present invention can also be used in the field of protecting industrial raw materials from microbial attack. In the present invention, the term “industrial raw materials” includes paper; carpets; buildings; cooling and heating systems; wall panels; ventilation and air conditioning systems, etc.; preferably, “industrial raw materials” is understood to mean wall panels. The compositions of the present invention can prevent adverse effects such as decay, discoloration, or mold growth.
[0122] The compositions of the present invention are typically formulated in various ways using formulation aids such as carriers, solvents, and surfactants. The formulations may be in various physical forms, such as powders, gels, wettable powders, wettable granules, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifying concentrates, microemulsifying concentrates, oil-in-water emulsions, oil flowables, aqueous dispersions, oily dispersions, suspender emulsions, capsule suspensions, emulsifying granules, soluble liquids, water-soluble concentrates (containing water or water-miscible organic solvents as carriers), impregnated polymer films, or other forms known from, for example, the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations may be used directly or diluted before use. Dilution can be performed, for example, with water, liquid fertilizers, micronutrients, bioorganisms, oils, or solvents.
[0123] Formulations can be prepared, for example, by mixing the active ingredient with formulation aids to obtain compositions in the form of finely powdered solids, granules, liquids, dispersions, or emulsions. The active ingredient may also be formulated with other aids such as finely powdered solids, mineral oils, plant or animal oils, modified plant or animal oils, organic solvents, water, surfactants, or combinations thereof.
[0124] The active ingredient can also be contained in microcapsules. Microcapsules contain the active ingredient in a porous carrier. This allows for the controlled release of the active ingredient into the environment (e.g., sustained release). Microcapsules typically have a diameter of 0.1 to 500 microns. They contain the active ingredient in an amount of approximately 25 to 95% by weight of the capsule. The active ingredient can be in the form of a large solid, fine particles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulation membrane may include, for example, natural or synthetic rubber, cellulose, styrene / butadiene + copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane, or chemically modified polymers and starch xanthetes, or other polymers known to those skilled in the art. Alternatively, the active ingredient can be contained in the form of finely ground particles in a solid matrix of a base material to form a fine microcapsule, but the microcapsule itself is not encapsulated.
[0125] Formulation aids suitable for the preparation of the formulations of the present invention are known in themselves. The following can be used as liquid carriers: water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl ester of acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,11-Trichloroethane, 2-Heptanone, α-Pinene, d-Limonene, Ethyl Lactate, Ethylene Glycol, Ethylene Glycol Butyl Ether, Ethylene Glycol Methyl Ether, γ-Butyrolactone, Glycerol, Glycerol Acetate, Glycerol Diacetate, Glycerol Triacetate, Hexadecane, Hexylene Glycol, Isoamyl Acetate, Isobornyl Acetate, Isooctane, Isophorone, Isopropylbenzene, Isopropyl Myristate, Lactic Acid, Laurylamine, Mesityl Oxide, Methoxypropanol, Methyl Isoamyl Ketone, Methyl Isobutyl Ketone, Methyl Laurate, Methyl Octanoate, Methyl Oleate, Methylene Chloride, m-Xylene, n-Hexane, n-Octylamine, Octadecanoic Acid, Octylamine Acetate, Ole Xylene, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols with higher molecular weights (amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc.), ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.
[0126] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soy flour, pumice, wood flour, crushed walnut shells, lignin, and similar materials.
[0127] Numerous surface-active substances can be advantageously used in both solid and liquid formulations, particularly in formulations that can be diluted with a carrier before use. Surface-active substances may be anionic, cationic, nonionic, or polymeric, and they can be used as emulsifiers, wetting agents, or suspending agents or for other purposes. Typical surfactants include, for example, alkyl sulfates such as diethanolammonium lauryl sulfate; alkylaryl sulfonates such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide addition products such as nonylphenol ethoxylate; alcohol / alkylene oxide addition products such as tridecyl alcohol ethoxylate; soaps such as sodium stearate; alkylnaphthalene sulfonates such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl) sulfoxynate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphates; as well as further substances described, for example, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey (1981).
[0128] Further auxiliary agents that may be used in pesticide formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoaming agents, complexing agents, neutralizing agents or pH adjusters and buffers, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, lubricants, dispersants, thickeners, antifreezes, fungicides, and liquid and solid fertilizers.
[0129] The formulations of the present invention may contain additives including oils derived from plants or animals, mineral oils, alkyl esters of such oils or mixtures of such oils, and mixtures with oil derivatives. The amount of the oil additive in the formulations of the present invention is usually 0.01 to 10% based on the applied mixture. For example, the oil additive can be added to the spray tank at the desired concentration after the spray mixture is prepared. Preferred oil additives include mineral oil, or plant-derived oils such as rapeseed oil, olive oil or sunflower oil, emulsified vegetable oils, alkyl esters of plant-derived oils such as methyl derivatives, or animal-derived oils such as fish oil or beef tallow. Preferred oil additives include alkyl esters of C8-C 22 fatty acids, particularly, C 12 -C 18 methyl derivatives of fatty acids (e.g., methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively)). Many oil derivatives are known from Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.
[0130] The formulations usually contain 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the compounds of component (A) and component (B), and 1 to 99.9% by weight of formulation aids (which preferably contain 0 to 25% by weight of surfactants). Commercially available products can preferably be formulated as concentrates, but the end user will usually use diluted formulations.
[0131] The application rate varies within wide limits and depends on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors depending on the method of application, the time of application, and the target crop. As a general guideline, the compounds can be applied at a rate of 1 to 2000 l / ha, particularly 10 to 1000 l / ha.
[0132] The specific compositions described above may exhibit synergistic effects. This always occurs when the combined action of the active ingredients is greater than the sum of the individual activity of the ingredients. The expected activity E for a given combination of active ingredients can be calculated according to the so-called COLBY formula as follows (COLBY, SR, "Calculating synergistic and antagonistic responses of herbicide combination". Weeds, Vol. 15, pages 20-22; 1967): ppm = milligrams of active ingredient (=ai) per liter of spray mixture Effect of active ingredient A) using X=p ppm Y = q ppm. Effect % by active ingredient B).
[0133] According to COLBY, the expected (active) effect of active ingredients A) + B) using p + q ppm of active ingredients is:
number
[0134] The combined effect is hyperadditive, or synergistic, when the observed effect (O) is greater than the expected effect (E). In mathematical terms, synergy corresponds to a positive difference in (OE). In the case of pure complementary addition of activity (expected activity), the difference (OE) is zero. A negative difference (OE) indicates a loss of activity compared to the expected activity.
[0135] However, apart from the actual synergistic effects with respect to fungicidal activity, the compositions of the present invention may also possess even more surprising advantageous properties. Examples of such advantageous properties that can be cited include: more favorable degradability; improved toxicological and / or biotoxicological behavior; or improved properties of useful plants (such as germination, crop yield, more developed root system, increased tillering, increased plant height, larger leaf blades, fewer basal leaves, stronger tillering, greener leaf color, less fertilizer required, less seeds required, more productive tillering, earlier flowering, earlier graining, less plant verse (lodging), increased shoot growth, improved plant vitality, and earlier germination).
[0136] The compositions of the present invention can be applied to plant pathogenic microorganisms, useful plants, their habitats, seedlings, stored products, or industrial raw materials threatened by microbial attack.
[0137] The compositions of the present invention may be applied to useful plants, their seedlings, stored products, or industrial raw materials before or after microbial infection.
[0138] The amount of the composition of the present invention applied will depend on various factors such as the composition used; the object to be treated (e.g., plants, soil, or seedlings); the type of treatment (e.g., spraying, dispersing, or seed coating); the purpose of the treatment (e.g., prevention or treatment); the type of fungus to be controlled; or the application time.
[0139] When applied to useful plants, component (A) is typically applied in amounts of 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, preferably 5 to 200 g ai / ha, for example 20, 50, 75, 100 or 200 g ai / ha, in relation to amounts of component (B) of 1 to 5000 g ai / ha, especially 2 to 2000 g ai / ha, for example 30, 60, 100, 250, 500, 800, 1000, or 1500 g ai / ha.
[0140] In agricultural applications, the application rate of the composition of the present invention depends on the type of effect desired, and is typically in the range of 20 to 4000 g of the total composition per hectare.
[0141] When the composition of the present invention is used for seed treatment, it is generally sufficient to use 0.001 to 50 g of compound (A) per 1 kg of seed, preferably 0.01 to 10 g of compound (B) per 1 kg of seed.
[0142] If any reference document, patent application, or patent is cited in the text of this application, the entire cited text is incorporated herein by reference. Another aspect of the present invention may be as follows: [1] A fungicidal and fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, Component (A) is the compound of formula (I): [C1] JPEG0007850153000011.jpg48170 (In the formula, R 1 This is hydrogen, -C(=O)CH 3 or -C(=O)CH 2 CH 3 And, R 2 is methyl or isopropyl, and R 3 (It is hydrogen or fluorine.) or its salts, enantiomers, tautomers or N-oxides; and Component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl N-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoro Methyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, ethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl [Tyl]-1,2,4-triazole-3-amine, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide and ethyl 1-[[5-[5-(trifluoromethyl)-1,2,A bactericidal and antifungal composition comprising a compound selected from the group consisting of 4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, or a salt thereof, enantiomer, tautomer, or N-oxide. [2] In addition to being different from component (B), methyltetrapol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metminostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, epoxyconazole, hexaconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidflumetofen, fluxapiroxad, sedaxane, bixafen, isopyrazam, fluopyram, fluindapir, isoflucipram, impilfluxad Mu, Quinofumeline, Ipupurfenoquine, Aminopyriphen, Fluazinam, Fludioxonil, Fenpicoxamide, Florylpicoxamide, Fenpropidine, Fenpropimorph, Mancozeb, Chlorothalonil, Cyclobtriflame, Cu-Oxychloride, Cu-Hydroxide, N'-[5-Bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine), N'-[5-Bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]- N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-(2-chloro-5-methyl-4-phenyl N'-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(3-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N'-(2-bromo-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N'-[2-bromo-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine,N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-isopropyl-N-methyl-formamidine, N'-[4-(2-cyanophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-4-(2-methylphenoxy)phenyl]-N-ethyl-N-methyl-formamidine, N-ethyl-N'-[4-(2-fluorophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-methyl- Formamidine, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy [C]benzonitrile, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazole-1-ylmethyl)cyclopentanecarboxylate, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol, N-methyl-4 -[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzenecarbothioamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide,The antifungal and antifungal composition according to [1], further comprising an additional active ingredient, component (C), selected from the group consisting of N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]cyclopropanecarboxamide, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethylisoquinoline, and 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethylisoquinoline. [3] Component (C), which is different from component (B), is methyltetrapol, azoxystrobin, trifloxystrobin, picoxystrobin, metminostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidflumetofen, sedaxane, isopyrazam, impilfluxam, fluazinam, florylpicoxamide, fenpropidine, mancozeb, chlorothalonil, cyclobutriflam, Cu-oxychloride, Cu-hydroxyl, N'-[5-bromo-2-methyl-6-(1-methyl-2-prop The antibacterial and antifungal composition according to [2] above, which is a compound selected from the group consisting of xy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, and N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine. [4] The antibacterial and antifungal composition according to any one of the above items [1] to [3], wherein the weight ratio of component (A) to component (B) is 20:1 to 1:40. [5] The antibacterial and antifungal composition according to any one of the above items [1] to [4], wherein the weight ratio of component (A) to component (B) is 15:1 to 1:30. [6] The antibacterial and antifungal composition according to any one of the above items [1] to [5], wherein the weight ratio of component (A) to component (B) is 10:1 to 1:10. [7] The bactericidal composition according to any one of the above items [1] to [6], wherein the weight ratio of component (A) to component (B) is 5:1 to 1:5. [8] The bactericidal composition according to any one of the above items [1] to [7], wherein the weight ratio of component (A) to component (B) is 4:1 to 1:4. [9] The bactericidal composition according to any one of the above items [1] to [8], wherein the weight ratio of component (A) to component (B) is 3:1 to 1:3.
[10] The bactericidal composition according to any one of the above items [1] to [9], wherein the weight ratio of component (A) to component (B) is 2:1 to 1:2.
[11] The bactericidal composition according to any one of the above items [1] to
[10] , wherein the weight ratio of component (A) to component (B) is 1:1.
[12] The fungicidal and fungicidal composition according to any one of the above items [1] to
[11] , further comprising an agriculturally acceptable carrier and optionally a surfactant and / or a compounding agent.
[13] A method for controlling or preventing plant pathogenic diseases, particularly plant pathogenic fungi, in useful plants or their reproductive materials, comprising applying a fungicidal / fungicidal composition described in any one of items [1] to
[12] above to the useful plants, their habitat or their reproductive materials.
[14] The method according to
[13] , wherein component (A) is applied to the useful plants in an amount of 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, preferably 5 to 200 g ai / ha, in relation to an amount of component (B) of 1 to 5000 g ai / ha, particularly 2 to 2000 g ai / ha, preferably 5 to 200 g ai / ha.
[15] The method according to
[13] or
[14] , wherein the composition components (A) and (B) are applied sequentially. [Examples]
[0143] The following examples serve to illustrate the present invention. The compounds (and compositions) of the present invention can be distinguished from known compounds (and compositions) by their high efficacy at low doses, which can be verified by those skilled in the art using the experimental methods outlined in the examples and, if necessary, by using small doses of the active ingredient, such as 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, or 0.2 ppm.
[0144] Throughout this specification, temperatures are expressed in degrees Celsius (°C), and "mp." indicates the melting point. LC / MS means liquid chromatography-mass spectroscopy, and the apparatus and methods (Methods A and B) are described below.
[0145] The LC / MS apparatus and method A are described below. Waters SQ Detector 2 Ionization method: Electrospray Polarity: Cations and anions Capillary (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00, Source temperature (°C) 150, Desolventing temperature (°C) 350, Cone gas flow (L / Hr) 0, Desolventing gas flow (L / Hr) 650 Mass range: 100~900Da DAD wavelength range (nm): 210~500 Method: Waters ACQUITY UPLC under the following HPLC gradient conditions (Solvent A: Water / Methanol 20:1 + 0.05% Formic Acid and Solvent B: Acetonitrile + 0.05% Formic Acid)
[0146] [Table 4]
[0147] Column type: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Column inner diameter: 2.1 mm; Particle size: 1.8 microns; Temperature: 60°C.
[0148] The LC / MS apparatus and method B are described below. Waters SQ Detector 2 Ionization method: Electrospray Polarity: Cation Capillary (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00, Source temperature (°C) 150, Desolventing temperature (°C) 400, Cone gas flow (L / Hr) 60, Desolventing gas flow (L / Hr) 700 Mass range: 140~800Da DAD wavelength range (nm): 210~400 Method: Waters ACQUITY UPLC under the following HPLC gradient conditions (Solvent A: Water / Methanol 9:1 + 0.1% Formic Acid and Solvent B: Acetonitrile + 0.1% Formic Acid)
[0149] [Table 5]
[0150] Column type: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Column inner diameter: 2.1 mm; Particle size: 1.8 microns; Temperature: 60°C.
[0151] If necessary, enantiomerically pure final compounds can be obtained from suitable racemic materials via standard physical separation techniques such as reversed-phase chiral chromatography, or by stereoselective synthesis techniques, for example, using chiral starting materials.
[0152] A typical description of a chiral analyzer is as follows: Supercritical fluid chromatography: Waters Acquity UPC 2 / QDa PDA Detector Waters Acquity UPC 2 Column: Daicel SFC CHIRALPAK(registered trademark) IC, 3μm, 0.3cm × 10cm, 40℃ Mobile phase: A:CO2 B:iPr Gradient: 0.5% B over 3.8 minutes ABPR: 1800 psi Flow rate: 2.0mL / min Detection: 247nm Sample concentration: 1 mg / mL in acetonitrile / i-propanol 50 / 50. Injection: 1 μL
[0153] Formulation example
[0154] [Table 6]
[0155] A wettable powder can be obtained by completely mixing the active ingredient with an auxiliary agent, thoroughly grinding the mixture in a suitable mill, and diluting it with water to obtain a suspension of the desired concentration.
[0156] [Table 7]
[0157] The active ingredient is completely mixed with an auxiliary agent, and the mixture is completely ground in a suitable mill to obtain a powder that can be used directly for seed treatment.
[0158] emulsifiable concentrate Active ingredients [components (A) and (B)] 10% Octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 mol ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50%
[0159] Any emulsion of the required dilution, suitable for plant protection, can be obtained from this concentrate by diluting it with water.
[0160] [Table 8]
[0161] A readily usable powder is obtained by mixing the compound with a carrier and grinding the mixture in a suitable mill. Such powders can also be used for drying and coating seeds.
[0162] Extruded granules Active ingredients [components (A) and (B)] 15% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%
[0163] The active ingredient is mixed with an auxiliary agent and ground, and the mixture is moistened with water. The mixture is then extruded and dried in an airflow.
[0164] Coated granules Active ingredients [components (A) and (B)] 8% Polyethylene glycol (mol. wt. 200) 3% Kaolin 89%
[0165] In a mixer, the finely ground composite is uniformly applied to kaolin moistened with polyethylene glycol. This yields coated granules that do not generate dust.
[0166] Suspension concentrate Active ingredients [components (A) and (B)] 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%
[0167] By thoroughly mixing the finely ground active ingredient with an auxiliary agent, a suspension concentrate can be obtained, from which a suspension of any desired dilution can be obtained by diluting it with water. Using such dilutions, living plants and plant reproductive bodies can be treated and protected from microbial ectoparasitism by spraying, pouring, or immersion.
[0168] Concentrated flowable formulation for seed treatment Active ingredients [components (A) and (B)] 40% Propylene glycol 5% Copolymer Butanol PO / EO 2% Tristyrenephenol + 10-20 moles of EO (2%) 1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%
[0169] By thoroughly mixing finely ground active ingredients with auxiliary agents to obtain a suspension concentrate, and then diluting this with water, a suspension of any desired dilution can be obtained. Using such a dilution, living plants and plant propagation materials can be treated and protected against microbial invasion by spraying, pouring, or immersion.
[0170] Sustained-release capsule suspension Mix 28 parts of the active ingredient combination [components (A) and (B)] with 2 parts of aromatic solvent and 7 parts of toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). Emulsify this mixture in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts defoamer, and 51.6 parts water until the desired particle size is obtained. Add a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water to this emulsion. Stir the mixture until the polymerization reaction is complete. Stabilize the resulting capsule suspension by adding 0.25 parts thickener and 3 parts dispersant. The capsule suspension formulation contains 28% of the active ingredient. The diameter of the medium-sized capsules is 8-15 microns. Apply the resulting formulation to seeds as an aqueous suspension in an apparatus suitable for the purpose.
[0171] Preparation Examples Compounds B.01 to B.15 in Table T1 were prepared using one of the synthesis techniques described in International Publication Nos. 2017 / 055469, 2017 / 055473, 2017 / 093348, 2017 / 118689, 2017 / 220485, 2018 / 065414, 2018 / 158365, 2018 / 177894, 2018 / 177880, 2018 / 219773, and 2019 / 002151.
[0172] If necessary, enantiomerically pure final compounds can be obtained from suitable racemic materials via standard physical separation techniques such as reversed-phase chiral chromatography, or by stereoselective synthesis techniques (e.g., by using chiral starting materials).
[0173] [Table 9-1] [Table 9-2] [Table 9-3] [Table 9-4]
[0174] Biological examples Example A1: Preventive control of Phakopsora pachyrhizi (soybean rust) / soybean / leaf blades. The entire soybean plant is treated with the active ingredient composition described above four weeks after planting. One day after spray application, leaflets are cut from the first trifoliate leaf. This is repeated five times with each dose. One day after treatment, Phakopsora pachyrhizi is sown on the leaflets. The leaflets are evaluated 11-14 days after sowing, and biological activity is derived from the relationship between treated and untreated ectoparasitic test plants. The amount of active ingredient used is shown in Tables 1-6 as g active ingredient (ai) / ha.
[0175] The results of the above tests are shown in Tables 1-6. These data indicate that synergistic fungicidal and mycogenic activity is observed with the combination of components (A) and (B) against Phakopsora pachyrhizi. According to Colby, mathematically, the synergistic factor SF corresponds to O / E. In actual agriculture, SF values of 1.0 or higher show a significant improvement that exceeds the purely complementary addition of activity (expected activity), while SF values of 0.9 or lower in actual application routines show a loss of activity compared to the expected activity.
[0176] [Table 10]
[0177] [Table 11]
[0178] [Table 12]
[0179] Table 13
[0180] Table 14
[0181] Table 15
Claims
1. A bactericidal composition comprising a mixture of components (A) and (B) as active ingredients, Component (A) is the compound of formula (I): 【Chemistry 1】 and; as well as Component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propaneamide A bactericidal composition comprising 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, or ethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate.
2. Ingredient (B) is different from the following: methyltetrapol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metminostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, epoxyconazole, hexaconazole, mefentrifluconazole, metconazole, benzovindiflupir, pidflumetofen, fluxapiroxad, sedaxane, bixafen, isopyraz The bactericidal composition according to claim 1, further comprising an additional active ingredient (C) selected from the group consisting of fluopyram, fluindapir, isoflucipram, impilfluxam, quinofumerine, ipupurfenoquin, aminopyriphen, fluazinam, fludioxonil, fenpicoxamide, florylpicoxamide, fenpropidine, fenpropimorph, mancozeb, chlorothalonil, cyclobutriflam, Cu-oxychloride, and Cu-hydroxyl.
3. The bactericidal composition according to claim 2, wherein component (C), which is different from component (B), is a compound selected from the group consisting of methyltetrapol, azoxystrobin, trifloxystrobin, picoxystrobin, metminostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidflumetofen, sedaxane, isopyrazam, impilfluxam, fluazinam, florylpicoxamide, fenpropidine, mancozeb, chlorothalonil, cyclobutriflam, Cu-oxychloride, and Cu-hydroxyl.
4. The bactericidal composition according to any one of claims 1 to 3, wherein the component (B) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide.
5. The sterilizing composition according to any one of claims 1 to 4, wherein the weight ratio of component (A) to component (B) is 15:1 to 1:
30.
6. The sterilizing composition according to any one of claims 1 to 5, wherein the weight ratio of component (A) to component (B) is 10:1 to 1:
10.
7. A sterilizing composition according to any one of claims 1 to 6, wherein the weight ratio of component (A) to component (B) is 5:1 to 1:
5.
8. A sterilizing composition according to any one of claims 1 to 7, wherein the weight ratio of component (A) to component (B) is 4:1 to 1:
4.
9. A sterilizing composition according to any one of claims 1 to 8, wherein the weight ratio of component (A) to component (B) is 3:1 to 1:
3.
10. A sterilizing composition according to any one of claims 1 to 9, wherein the weight ratio of component (A) to component (B) is 2:1 to 1:
2.
11. A sterilizing composition according to any one of claims 1 to 10, wherein the weight ratio of component (A) to component (B) is 1:
1.
12. A sterilization composition according to any one of claims 1 to 11, further comprising an agriculturally acceptable carrier.
13. The bactericidal composition according to claim 12, further comprising a surfactant and / or a compounding agent.
14. A method for controlling or preventing plant pathogenic fungi in useful plants or their reproductive materials, comprising applying the fungicide composition described in any one of claims 1 to 13 to the useful plants, their habitat or their reproductive materials.
15. The method according to claim 14, wherein component (A) is applied to the useful plant in an amount of 5 to 200 g a.i. / ha, and component (B) is applied in an amount of 5 to 200 g a.i. / ha.
16. The method according to claim 14 or claim 15, wherein the composition components (A) and (B) are applied sequentially.
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