TW200916444A - Pyrazole carboxylic acid derivative, method of producing same and fungicide - Google Patents

Abstract

The present invention provides a fungicide which exhibits an agricultural disease control action and is harmless, or mostly harmless, to crops. The fungicide of the present invention contains a pyrazole carboxylic acid derivative represented by the following formula (1) as an active ingredient: In formula (1), R1 represents an alkyl group and the like, R2 and R3 each independently represent a hydrogen atom, a haloalkyl group and the like in which at least one of R2 and R3 is a haloalkyl group having 1 to 6 carbon atoms, A represents-OR4, -SR5, -NR6R7 or -NR8NR9R10 in which R4represents an alkyl group having 3 to 12 carbon atoms and the like, R5 represents an alkyl group having 1 to 12 carbon atoms and the like, R6 represents a hydrogen atom and the like, R7represents an alkyl group having 5 to 12 carbon atoms, and R8, R9 and R10 each represent an alkyl group having 1 to 12 carbon atoms and the like.

Description

200916444 VI. Description of the Invention: [Technical Field to Be Invented by the Invention] The present invention is directed to a biological and pure method for the recording of sinus, and a bactericidal agent which is an active ingredient of a 5-quinoxazolecarboxylic acid derivative. [Prior Art] The task of treating the disease is very big. Especially rice rice heat ίί has a variety of fungicides for research and development and application. It is known that some kind of living organisms have (4) activity (such as the Japanese patent special opening 9-i76i25, the male mouth is also soft 'having a toothed alkyl group and a nitrogen atom with a substituted benzene ring, the ratio of the indole bond is 2%ϋ ί 3 has herbicidal activity and insecticidal activity (for example, refer to Japanese Patent Laid-Open No. Hei 2-53775, JP-A No. 2-129171). In addition, from the point of view of the question of the brother-in-law, it is safe and Low-concentration sound energy, Λ harmful bacteria. h and low secret enough to prevent and cure [invention content] "The subject to be solved by the invention" Gan = Patent Unexamined-Japanese-Patent No. 9-176125, "The ratio of reading acid derivative = and "Killing: Unexamined-Japanese-Patent No. 2-129171, and the method of solving the problem", and the synthesis of various novel pyrazolecarboxylic acid-derived compounds, or compounds which are rarely harmful, The present invention has been completed. = The specific method for solving the above problems is as follows. The pyrazolecarboxylic acid derivative represented by the following general formula (1).

General formula (1) [wherein R1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and R2 and R3 each independently represent a hydrogen atom, a carbon atom having 1 to 6 carbon atoms, and a carbon atom number of 1 to 6; a halogenated alkyl group, an alkoxy group having 1 to 6 carbon atoms, a halogenated alkoxy group having a valence of 2, 6 or less, an alkylthio group having 1 to 6 carbon atoms, and a halogenated olivine having a carbon number of 丨6 A sulfonyl group having 1 to 6 carbon atoms, a sulfinyl group having 1 to 6 carbon atoms, an alkanesulfonyl group having 1 to 6 carbon atoms, and a carbon number of 丨6. _ alkane fluorenyl, _ atom, cyano or a base. However, at least the number of r2 and r3 is 1-6. A ' A represents an OR4, an SR5, an NR6R7 or an NR8NR9R10. R represents a non-reactive atomic group of 3 to 12, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, and 2 carbon atoms. An alkynyl group of hexamethylene, an alkyl group having a carbon number of 丨~6 substituted with a heteroaryl group which may be substituted, an aryl group, or a heteroaryl group which may be substituted. R represents a group having a stone inverse number of 1 to 12, a ring group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, and 2 to 6 carbon atoms. 6 an alkynyl group, a heteroaryl group which may be substituted by a heteroaryl group, or a heteroaryl group which may be substituted. For example, R7 represents a group having 5 to 12 carbon atoms, a group having 3 to 6 carbon atoms having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, and a carboxyl group substituted by a carboxyl group. When 6 is burned or replaced by a carbon atom with a carbon number of 丨~6, the carbon atom is 1~6 green, and R6 represents a hydrogen atom, a carbon atom of 丨~12, and 1^2~6 Alkenyl group, cycloalkenyl group having 3 to 6 carbon atoms, number of carbon atoms, 6 ΐ ΐ 取 ί 取 ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί彡元私友基, or a arylamine group. 200916444 Further, when R7 represents a cycloalkyl group having 3 to 6 carbon atoms and a substituent which can be substituted, 卩6 represents a ring-like group having a face number of 2 to 6 or 2 or 6 carbon atoms. ~6 block base, can be taken from the third generation of heteroaryl, county, burning oxygen, aryl oxygen county, burning m to the amine group, or aromatic amine record. The extraterrestrial base, R, R and Γ are independent, indicating that the hydrogen atom, the number of carbon atoms 丨~丨卩ί:4ί, the number of carbon atoms 2~6, the number of carbon atoms 兀3:6, can be replaced A halogen-substituted carbon atom, H, an aryl group which may be substituted, a heteroaryl group which may be substituted, a fluorenyl group, a anaerobic oxycarbonyl group, an alkane sulfonyl group, an aryl sulfonyl group, an amine carbonyl group, or an aromatic amine Rebel. However, the case where '9 does not contain R8, R9 and R1Q is a hydrogen atom. And R may be bonded to each other to form a heterocyclic group having 2 to 4 carbon atoms. The pyrazolecarboxylic acid derivative described in the above &lt;:1&gt;, wherein R of the general formula (1) represents a functional alkyl group having 1 to 6 carbon atoms. The pyrazolecarboxylic acid derivative described in the above <2>, wherein the general formula (1) f is a group having 1 to 6 carbon atoms, R 2 is a fluorine-based group having 1 to 6 carbon atoms, and R 3 is a hydrogen atom. The pyrazolecarboxylic acid derivative described in the above formula (1), wherein A of the general formula (1) is an NRR or - with nr9r10. &lt;4&gt;^5-, a method for producing a pyrazole decanoic acid derivative, which is produced by the above-mentioned &lt;i&gt;~, the ratio of the salicylic acid derivative, which comprises the following general formula (2) and the following - The process in which the compound represented by the general formula (3) is subjected to a reaction.

• General formula (2) [wherein, 'V, R2, and R3 are the same as RHR3 of the general formula (1), respectively. 200916444 General formula (3) [wherein 'A is the same as the definition of a of the general formula (1). And a carbazolecarboxylic acid derivative according to any one of the above-mentioned <1> to <4>, which is represented by the following general formula (4), which is a method for producing a pyrazole acid derivative. A process in which a compound is reacted with a compound represented by the following general formula (3). R2

1 Ο General (4) A· General formula (3) [wherein, A is the same as A of general formula (1). ] &lt;7&gt; - a fungicide containing at least the above &lt;1&gt;~ slow acid derivative! Kind # do the active ingredients. Any of the above-mentioned bactericidal agents described in the above-mentioned &lt;7&gt;, is a bactericidal agent for agricultural and horticultural use. According to the present invention, it is possible to provide an excellent performance of the plant a for controlling rice rice fever, and at the same time 'In particular or very little harm, it is a carboxylic acid derivative. Only T is useful in any useful crop. [Embodiment] The present invention is described below. 7 200916444 The pyrazolecarboxylic acid derivative of the present invention is represented by the following general formula (1) ) indicates R2 R3

In the general formula (1) W and ί ii, R represents a hydrogen atom or a carbon atom having a carbon number of 1 to 6; R and R are each independently 'representing a hydrogen atom, a number of carbon atoms, and a number of calories. The appearance base, the number of carbon atoms, the alkoxy group of carbon 6, the carbonogen, the calcination of j 1 , the base, the number of carbon atoms 丨~6, the sulfur-burning group, the number of carbon atoms, the number of carbon atoms, 1 to 6 Alkylsulfinyl group, a toothed group having 1 to 6 carbon atoms, a halogenated group having 1 to 6 atomic number, a halogenated group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a schloss group. However, at least the square of R2 and R3 is a dentate alkyl group of the number 1 to 6 of the stone. In the present invention, from the viewpoint of bactericidal activity, R2 is a purely calcined rA having a carbon number of 1 to 6, and the general formula (1) is a two-atom atom having 1 to 6 carbon atoms. The number of fluoroalkyl groups is 1 to 6, and R3 is more preferably a hydrogen atom.乂士:又^ Γ) ’ Α indicates —〇R4, —SR5, —NR6R?, or —NRS_i〇. a group, a carbon atom number, an alkyl group, a carbon atom of -6, a ring-burning η. , an alkenyl group having an alkyl group of 3 to 6 and a carbon number?

i substituted by a heteroaryl group substituted with a heteroaryl group substituted with a carbon atom having 1 to 6 carbon atoms, a square group which may be taken, or a heteroaryl group which may be substituted. a filament of J ρί ϋ2, a Wei group having a carbon number of 3 to 6, a radical having a carbon number of 3 to 6, a carbon atom + a number 2, or a carbon atom of 1 to 6 of 'gig a carbon atom which can be replaced by a calcining group of 5 to 12, an alkenyl group having 2 to 6 carbon atoms, a carbon ', a metabosic, or an alkoxycarbonyl group substituted with a carbon number of 1 to 6; In the case of an alkyl group having 1 to 6 carbon atoms, R6 represents a hydrogen atom, a rare carbon group having a carbon number of 丨~丨卩^2 to 6, a lysine having 3 to 6 carbon atoms, a number of carbon atoms U, a group, and the like. Heteroaryl, aryl, 6 oxo, aryloxy, skeletal, arylsulfonyl, alkylamine carbonyl, or arylamine carbonyl.兀κ _ ^ shows a cycloalkyl group having 3 to 6 carbon atoms, an aryl group which may be substituted, or a (tetra) group which may be substituted, and p represents a ring group of 2 to 6 carbon atoms; An alkynyl group having 2 to 6 carbon atoms, an aryl group which may be substituted] may be taken as an ί, ί, 芳, sulfonyl, arylsulfonyl, alkane, or arylamine carbonyl group. . The soils R, R and ... are each independently, and represent a hydrogen atom, a ring carbon having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a filament having 2 to 6 carbon atoms, and a material which can be substituted. The genus of 丝^6 巧 山 可 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 Aromatic amine plate base. However, the case where R8 and RlQ are not hydrogen atoms is not included. ^β and Γ can also be bonded to each other to form a heterodole having a carbon number of 2 to 5 - from the viewpoint of bactericidal activity, the "-nr6r7 acid derivative of the general formula (1) is preferred; and the general formula (1) A is One is the carbon atom number b 6 pure silk of the wealth of the derivative of the more ΪΪ β ΪΪ 以 ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ί ― ― ― ― ― ― ― , R3 money shot of the combination of the base of the calorie is 'in the general formula (1), R1 is a methyl group, the number of ^12 nitrogen atom 'A is, V, R6 is a hydrogen atom, R? is a carbon source = rm combination; Or ri is methyl, r2 is trifluoromethyl, R3 is the base of nitrogen 12, sulfonate is replaced by R, and R7 is the number of greens 5~ too square or can be replaced The combination of aryl groups. The combination of aryl, ίίΐ ίί ΐ , , 为 — — — — — — R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R a combination of a carbon number of 5 to 12; or γ is a methyl group, a r 2 j hydrogen atom, a is -_, r6 is a aryl group, and R7 is a derivative of the ruthenium acid which can be used in the present invention. Number of methyl: ethyl, propyl, butyl , pentyl, hexyl, etc., the upper two π exemplified by butyl, pentyl, hexyl, heptyl, octyl, oxime H zhang 3 12 alkyl, dodecyl, etc., the above two carbon atoms Tiantu, eleven J 1; e. base, dodecapine, etc., the above-mentioned carbon atom number 5~12 appearance base can be said to be heptyl, octyl, decyl, decyl, undecyl, twelve Alkyl and the like. In addition, the soil and the halogenated compound with a carbon number of 1 to 6 may be a trifluoromethane group, a fluoromethyl group, a gas difluoromethyl group, a bromodifluoromethyl group, a tris-methyl group, a triterpene 7-methyl group: ,-? base, pentafluoroethyl, trichloroethyl, tribromoethyl, trifluoropropyl, all: factory! The fluoroalkyl group of ～6 may, for example, be a trifluoromethyl group, a difluorof group, a fluorodioxime ethyl group, a pentafluoroethyl group, a trifluoropropyl group or a perfluoropropyl group. Soil A carbon number of 1 to 6 recorded methoxy, ethoxy g, Q carbon = number! The ethoxy group of ~6 is exemplified by a trifluoromethoxy group, a bis(ethylene) oxyethylene group, a hexyloxy group, a hexyloxy group, a hexyloxy group, a hexyloxy group, a sulfonyl group having 1 to 6 carbon atoms, and a trithiol group. Base, trifluoroethylthio, triterpenoid, on,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, The base can be lifted by three gas ^ ^ = Ethylene continued sulfhydryl, three gas and ethyl sulphide fine base, etc., the above carbon ^ ί ϊ ί can be a heteropoly group, a B group, etc., the above number of magnetic atoms of the trifluoromethane The group, the trifluoroethylene, the trichloroethane, the halogen atom, the fluorine atom, the fluorine, the chlorine, the bromine, the earth, etc., the carbon 6 B = said: thin, butadiyl, pentyl, hexyl, etc. The number of atoms of human 3~6 can be raised as ring_base, nail alkenyl, cyclopentyl group 10 10 200916444

Further, the above-mentioned block having 2 to 6 carbon atoms may, for example, be an ethyl group, a propyl group, a butynyl group, a pentynyl group or a hexynyl group. The above heteroaryl group can be defined as a base, ♦ 固 固 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金 金Junji, sputum, sputum, sputum, sputum, sputum, scorpion, scorpion, sputum, benzene (tetra) phenyl, ke, ke. Sitrate, benzopyrene, benzoisoindolyl, and the like. U-recording of the above-mentioned carbon material 5 2~5 of the transfer of odor storage, thio-wei group, aZiridlnyl, pyrrolidinyl, piperidinyl, piperylene, pyrrolyl and the like. And the substituents of the silk which can be replaced by the Ϊi' Ϊ 及 及 及 及 及 及 及 , , , , , , , , , , 取代 取代 取代 取代 取代 取代 取代 ' ' ' ' ' ' ' ' ' ' ' ' ' And hexyl ketone base; three chaotic methyl, difluoromethyl, bromine, methyl and di-ethyl ester substituted calcination; methoxy, ethoxy, propoxy and butoxy oxime The methoxy group, the difluoromethoxy group and the trifluoroethoxy ethoxylate are substituted for the calcined base, the thiol group, the ethylthio group, the propylthio group, the butylthio group and the like; the trimethylthio group and the second group Substituting thiol and trifluoroethyl silk to replace sulphur-thiol; sulphate, sulphate, sulphate, sulphite, and stellite base; tri-gas sulphate Guji and trifluoroethyl sulfhydryl groups are more suitable for the replacement of daunxine; sulfonyl sulfonyl, ethyl sulfonate, propyl sulfhydryl and butyl sulfhydryl; trifluoromethane xanthine, difluoromethyl A sulphate group such as a fluorenyl group and a trifluoroethylene group, such as a sulfonium fluorenyl group, an acetoguanamine group, an amidoxime group; Difluoromethyl continued g! silk, diamylamine and three B stuffed stone yellow spot amine group substituted with a halogen group element Si; fluorine, chlorine, bromine, carbon atoms of the functional element;. Cyano; nitro; acetyl group, benzoyl and the like acyl groups. The above sulfhydryl group may be an alkylcarbonyl group such as an ethenyl group, an aromatic carbonyl group such as a benzoquinone group or a heteroarylcarbonyl group such as a succinylcarbonyl group which may be substituted; and the above-mentioned alkoxycarbonyl group may be a methoxycarbonyl group or a propoxy group. The above aryloxy group may be a phenoxy group or the like. The alkanesulfonyl group may be a methylsulfonyl group or a propyl sulfonyl group; the above arylsulfonyl group may be a benzenesulfonyl group, and the above amine group may be an amidino group, a propylamine group or the like; The carbonyl group may, for example, be an aniline carbonyl group or the like. '200916444 &lt;Production Method (A) of Pyrazole Carboxylic Acid Derivatives> The method for producing an indolecarboxylic acid derivative of the present invention (A) 'comprises the compound represented by the following general formula (2) with the following general formula ( 3) A process in which the indicated compound is subjected to a reaction. That is, the 11 ratio of the present invention. The taustic acid derivative can be produced by the reaction represented by the following reaction formula (1). Reaction formula (1)

In the reaction formula (1), R1, R2, R and VIII are respectively defined in the same manner as R1 R3 and A in the general formula (1). In the reaction formula (1), a pyrazolecarboxylic acid derivative represented by the general formula (2) and a compound represented by the general formula (3) are subjected to a condensation reaction in a solventless or solvent to produce a pyrazolecarboxylic acid derivative represented by the formula (1). . No.: carboxylic acid can be used according to Japanese Patent Laid-Open No. 2 - (3) Table x shows nr8nr9r1&gt; 'The use of a general inorganic acid or an organically usable salt is not particularly limited, and the cardiac reaction formula (1) can also be used as a service agent. Carry out the reaction. Can be used #HCl, gasification-2 - gas - l 3 _ dimethyl 'mi:: amine (tetra) carbodiimide · When using a condensing agent, the amount of condensing agent used is 1 to 2 molar equivalents, And H. 2 Moer^^(2) is not shown in the reaction formula (D when solvent is used, solvent and I material Χ | 机 machine solvent can be. Specific examples are water; methanol, agent or An alcohol such as butyl alcohol; 12 200916444 Dihydrosilane, chloroform, etc.; aromatic hydrocarbons such as benzene, toluene, and diphenyl; aliphatic hydrocarbons such as hexane and heptane; Baseline amine (DMF), dimercapto-ethyl-month-' (DMA), sputum stone (DMS0), 1,3 -dimercapto-2_ σ mugh alpha ketone (bribe), 1 _ Aprotic polar solvent such as mercapto-2-pyrrolidine (gift); diethyl _, isopropyl sulfonate, 1,2-dimethoxy ethane (dme) 'tetrahydrofuran (THF), di-n-halo, etc. Ethers: nitriles such as r睥 and propionitrile, etc., 'intestines, expressed in the reaction formula (1), general formula (2). The amount of the compound used in the formula (3) is 1 to 2 molar equivalents, and i to L 2 molar equivalents ^. Further, the above reaction formula (1) The reaction temperature and the reaction time can be changed in a wide range. In general, the reaction temperature is 1 (TC~2〇〇. (:, and ^(:~丨(10) is better. Further 'reaction time 〇· 01~5〇小时, and preferably 〇. 1~15 hours. &lt;Production method of pyrazolecarboxylic acid derivative (B) &gt; The method for producing pyrazolecarboxylic acid derivative of the invention B) 'containing a process for reacting a compound represented by the following formula with a compound represented by the following general formula (3). That is, the pyrazolecarboxylic acid derivative of the present invention can be represented by the following reaction formula (2) 1 should be manufactured. Reaction formula (2)

In the reaction formula (2), R1, R2, R3 and A are the same as defined in the general formula (1), R1, R2, R and A, respectively, and γ is a leaving group. The leaving group represented by Y can be used in the present invention by a de-radical which is usually used in a condensation reaction. Specific examples thereof include a halogen atom represented by a gas atom, an alkoxy group represented by a decyloxy group and an ethoxy group, an aryloxy group represented by a phenoxy group, an ethoxy group represented by an ethoxy group, and a methoxy group. The carbonyloxy group represents an alkoxycarbonyloxy group, an arylcarbonyloxy group represented by a phenylcarbonyloxy group, an N-hydroxysuccinimide, a 1-hydroxybenzotriazole, an imidazolyl group and the like. 13 200916444 - It is shown that the compound represented by the general formula (4) and a compound are reacted in a solvent-free or solvent in the reaction formula (2) to give a pyrazolecarboxylic acid derivative. The slave type (丨) indicates that the reaction represented by the reaction formula (2) can be carried out in the presence of a base, and the above-mentioned alkali is not particularly limited. The inorganic base or the hydrazine-decomposing metal test metal-hydrogenated steel, Potassium hydride, sodium ethoxide, etc., metal oxide alkoxides, sodium oxide, etc.:, potassium carbonate, sodium carbonate and other carbonates, acid acid three clocks, dish acid trisodium quinones, hydrogen carbonate dihalon, etc. Phosphate, acetic acid sodium, acetic acid clock and other acetic acid unloading, Dendrobium diamide. Amino group ratio, triethylamine, diazabicyclo-2, H ring

Cdiaza-bicyclo-undecene) and other organic tests.埽 When a base is used in the reaction formula (2), it can be used as a solvent of the reaction formula (2) when it is used in an amount of an organic base. ..., meaning j. In particular, the reaction temperature and reaction time of the above reaction formula (2) are used. In general, the reaction temperature is -赃~·. c, and then change again, the reaction time is 〇. 〇 1~50 hours, and 15 hours is better.化合物 The compound represented by the above formula (4) can be produced by the above-mentioned carboxylic acid. For example, the above-mentioned general formula (2) is represented by (four) ϊ^ί, gas, phosgene, chlorinated scale, three gasification disc, five gasified phosphorus: bromine, phosphorus tribromide, diethylamine Sulfur fluoride, ], imidazole, etc. are produced by reaction. Further, the compound represented by the general formula (4) can be reacted with an alcohol represented by the general formula (2) and an alcohol such as methanol or ethanol in the absence of a catalyst or a catalyst according to a usual method. &lt;Fungicide&gt; 14 200916444 • A fungus containing at least one of the above-mentioned general formula (1), which is represented by the above formula (1), as an active ingredient. According to this, the role of plant diseases in the age of health can be controlled. The use of the bactericide of the present invention is not particularly limited, and it can be used as an industrial bactericide for antisepsis, mildew resistance, etc., a bactericidal agent for agricultural and horticultural use, a sterilizing agent for medical use, and the like. Since the fungicide of the present invention exhibits a plant disease control effect, it is particularly preferred as a fungicide for agricultural and horticultural use. + The bactericide of the present invention can be used for belonging to the order of the genus Oomycetes, Ascomycetes, incomplete genus (j) euteromycetes, Basidiomycetes, and the genus Piasm〇di〇 ph〇romyCetes) and various plant diseases caused by other pathogens such as vegetables, fruit trees, rice, cereals, flowers, and turf. Next, the specific disease name (pathogenic name) which can use the fungicide of the present invention is exemplified as a non-limiting example. Rice blast disease (Magnaporthe grisea (Pyricularia oryzae)), flax leaf blight (Cochliobolus miyabeanus), Rhizoctonia solani, Gibberella fujikuroi, Pythium iKPythium (Pythium graminicola, etc.); powdery mildew of wheat (Erysiphe gramiis f.sp. hordei; f.sp. triici), Pyrenophora graminea, Pyrenophora teres (net spot), scab ( Gibberella zeae), rust (Puccinia striiformis; P. graminis i P. recondite i P. hordei), snow rot (Typhula sp. &amp; Micronectriella nivalis), smut (Ustilago tritici &amp; U. nuda), eye Pseudocercosporella herpotrichoides, Rhynchosporium secalis, Septoria tritici, Leptosphaeria nodorum, Pythium brown rot (Pythium iwayamai, etc.); Grape Plasmopara viticora, Uncinula necator, Elisinoe ampelina, late rot (Glomerella 15 200916444 ci Ngulata), Phakopsora ampelopsidis; Podosphaera leucotricha, Venturia inaequalis, Alternaria alternata, apple pathotype, Gymnosporangium yamadae, Monlia disease (Sclerotinia mali) ), rot (Valsa ceratosperma); pear black spot disease (Alternaria alternata, Jpanese pear pathotype), black star disease (Venturia nashicola), brown spot disease (Gymnosporangium haraeanum); Pear disease P (hytophthora cactorum); r peach Brown rot (Sclerotinia cinerea), Scadosporium carpophilum, Phomopsis sp., Phytophthora sp.; Colletotrichum gloeosporioides, deciduous disease (Cercospora kaki; Mycosphaerella nawae); Psudoperonospora cubensis, Phytophthora meIonis, Phytophthora nicotianae, Phytophthora drechsleri, Sphaerotheca fuliginea, Colletotrichum lagenarium, Bacterial wilt (Mycosphaerella mr\ 1 ^ * niv^ i Uni oy , Phytophthora infestans, Pythium vezans &amp; Rhizoctonia solani, Alternaria solani, Fluvia fulva, Pythium myriotylum & Pythium dissotocum ); Erysiphe cichoracorum, Phytophthora infestans, Phytophthora capsici; Alternaria japonica, Cercosporella brassicae, Plasmodiophora Brasicae), Peronospora brassicae; Phytophthora porri, rust (Puccinia.allii); 16 200916444 Phytophthora megasperma, Peronospora manshurica, purple spot (Cercospora) Kikuchii), Elisinoeglysines, Diaporthephaseololum; Colletotrichum lindemuthianum; Mycosphaere 11 a berke 1 ey ii, Mycosphaerella arachidis; Bean powdery mildew (Erysiphe pisi), dew disease ( Peronospora pisi); Phytophthora infestans, Alternaria solani; Exobasidium reticulatum, Elisinoe leucospila; Alternaria longipes, powdery mildew (Erysiphe) Cichoracearum), Colletotrichum tabacum; Cercospora beticola, Peronospora schachtii; Diplocarpon rosae, Peronospora sparsa, Phytophthora megasperma ), powdery mildew (Sphaerotheca pannosa); Sepia chrysanthemi-indici, Puccinia horiana, Phytophthora catctorum; Sphaerotheca humuli, Phytophthora nicotianae, Pythium ulutimum; Botrytis cinerea, Sc 1 erot inia sc 1 erot i orum; Rhizoctonia solani , Sclerotinia homoeocarpa, Curvularia (Curvularia) Geniculata), Puccinia zoysiae, Helminthosporium, Cochiliobolus sp., Rhynchosporium secalis, Magnaporthe grisea (Pyricularia oryzae), Blight 17 200916444 ( Gaeumannoinyces graminis), Anthracnose (Coilet〇trichum 'graminicola), Typhula incarnate, Typhula ishikariensis, Xcleostima boreaiis, Fairy Marasmius 〇reades, Pythium aphanidermatum, etc. &quot; Among them, the general formula (1) shows that the sputum acid derivative is particularly excellent for the rice blast grisea (Pyricularia), and there is no special drive for the use of the invention. The bactericide used in the present invention may be used alone or as a mixed preparation of the substance. That is, the shots are all improved or fertilized and 'in the fungicide of the present invention', the 0 is more limited than the saliva derivative, such as can directly contain the wow ship derivative = ',,, body or liquid _ The mixed-filled towel 2 3 is preferably solidified with the bag 3 to be contained in the above composition. Here, it is a synthetic or natural inorganic or organic substance that is required to be treated in a convenient manner to facilitate the active ingredient. In the present invention, suitable for solid (_tmorillonite), kaolin ^ ^ such as montmorillonite talcum powder, vermiculite, stone *, stone 'four soil, white clay, organic matter: Large, powder, wheat flour and other plants 4 machines and: #. Examples of liquid carriers which are not suitable for sulfur, such as toluene, dioxane, hydrocarbons; kerocene hydrocarbons such as kerosene and oils; tetrakis; (c?r) a: an isocyanated hydrocarbon; Propylene, acetophenone; imitation, ethers such as glyme; alcohols such as methanol, ethyl i, tetrahydrofuran, carbamazepine, dimethyl sulfoxide, i- acetyl ethoxylate; And water, etc. M-transfer to proton polar solution The killer of the present invention may further contain various adjuvants. Auxiliary financial purposes should be used 18 200916444. Auxiliary agent can be used alone or in combination of two or more kinds to make polyoxyalkylene sulphonate and sulphur: salt, sulphuric acid sulphate, agent; polyoxy- sinter = anionic interface polyoxy olefin wire Amine oxyalkylene amide, fatty acid brewing, sorbitol liver II::: Oxygen: acid brewing, glycerin and polyoxypropylene polyoxyethylene late stage poly-alcoholic fatty acid lysyl methyl cellulose, casein, A腆 / Zhe II, methyl cellulose, carboxy in the above. &gt; 4. However, the specific adjuvant component is not limited to the amount of the fungicide of the present invention, and is usually in the powder of 〇.5~2 (^^OS3°f acid derivative is 〇5~90 heavy denier. Know as 〇 · 5~50% by weight, can be thirsty

~(10)趟., but ==1~2° heavyweight water suspension agent is U % ; J 60^99 tt , heavyweight water 10~9_, granules of normal powder is 0·1~20% by weight ',·]卞丨f in the t and 'about the adjuvant content, pass -20 ί#%, ί*! °· 1 J: and other carrier content, adjuvant content in the 'two 1 to 丄 ~ plus weight%. Appropriate adjustment of sex, application place, etc. Having considered the physical and chemical properties of the formulation, the "Examples" are defined as: 4 mils basis without (Example 丨)" of these examples unless otherwise stated. Fluoromethyl- 1Η-t»比嗤-5 __ ,, <Synthesis of methyl-disc-octyl _3_ kinamine (Compound No. 57) &gt; 19 200916444 Addition of sulfazone x〇mL in i-甲美A • carboxylic acid l. 〇g, heated reflux 2 secret one methyl-H-pyrazole-5~ Under the decompression, take care of (four) points. , ° ^ 亚 亚 醯 醯 , 加 加 加 加 加 加 加 , , , , , , , , , , , 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 81 Wenxia Lion 4 tree. The liquid layer of this reactor was dried with sulphuric acid, and after 2 times of extraction with 3 GGmL of formazan, it was refined (solvent 1 匕, gluten. The residue obtained was obtained by gel column chromatography (solid brown solid) The title compound h. <Synthesis of 1-methyl-N-n-octyl-3-trifluoromethyl_11{_pyridinium carboxamide (Compound No. 57) &gt; 5 Its methyl _ 3 ~ two gas Methyl-1H 吼 吼 — 5 一 一 一 一 Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Ul Hydrochloride l lg. Stir two liters of dichlorosilane (200 mL) at room temperature and wash with water. The organic layer was treated with magnesium sulfate. The residue was purified by Shixi rubber column chromatography (washing) Solvent: di-methane/hexane), the title compound of the pale brown solid is 1.0 g, and the following (4) is combined with the above-mentioned Example 1 and Example 2 to produce the same age; that is, the following formula (5)~ Formula (8) The compound examples shown are as follows: Table 1 to Table 11. The physical property values of several of the compounds are shown in Table 12 to Table 19. Further, Me in the table is a mercapto group, Et is an ethyl group, and i-Pr is Isopropyl, n_Pr = propyl ' n - Bu is n-butyl, c _ Hex is cyclohexyl, Bn is a benzyl group, ph is stupid, vinyl is vinyl, anyi is allyl, pr〇pargyl is alkyne Propyl, Ac is ethyl ketone group 'Bz is a ruthenium group, and Naph is a naphthyl group. 20 200916444 [Table 1] R2

\R4 (5) Compound No. R 1 R 2 R 3 R4 1 Me CF3 H i-Pr 2 Me CF3 H n-Bu 3 Me CF3 H n-C8H17 4 Me CF3 H c-Hex 5 Me CF3 H al ly 1 6 Me CF3 H propargy1 7 Me CF3 H Ph 8 Me CF3 H cf3 \ Me 9 Me CF3 H Υλ 10 ' Me CF3 H VII 11 Me CF3 H o 12 H CF3 H c-Hex 13 H CF3 H Ph 14 Me CF3 Cl c- Hex 15 Me CF3 Cl Ph 16 Et CF3 H c-Hex 17 Et CF3 H Ph 18 i-Pr CF3 H c-Hex 19 i-Pr CF3 H Ph 20 Me i-C3F7 H c-Hex 21 Me i-C3F7 H Ph 22 Me CF3 H n-C12H25 21 200916444 [Table 2] R2

R5 Compound No. R 1 R 2 R3 R5 23 Me CF3 H Me 24 Me CF3 H Et 25 Me CF3 H i-Pr 26 Me CF3 H n-Bu 27 Me CF3 H n-C8H17 28 Me CF3 H c-Hex 29 Me CF3 H al lyl 30 Me CF3 H propargyI 31 Me CF3 H Ph 32 Me CF3 H CFa \ Me 33 Me CF3 H 34 Me CF3 Lj -o 35 Me CF3 H -^;3 36 H CF3 H Me 37 H CF3 H c-Hex 38 H CF3 H Ph 39 Me CF3 Cl Me 40 Me CF3 Cl c-Hex 41 Me CF3 Cl Ph 42 Me CF3 N02 Me 43 Me CF3 CN Me 44 Me CF3 Me Me 45 Me CF3 OMe Me 46 Me CF3 S02Me Me 22 200916444 Table 3] Compound No. R 1 R 2 R 3 R 5 47 Et CF3 H Me 48 Et CF3 H c-Hex 49 Et CF3 H Ph 50 i-Pr CF3 H Me 51 i-Pr CF3 H c-Hex 52 i-Pr CF3 H Ph 53 Me n-C3F7 H Me 54 Me i-C3F7 H Me 55 Me i-C3F7 H c-Hex 56 Me i-C3F7 H Ph 23 200916444 [Table 4]

(7) Compound No. R 1 R2 R 3 R6 R7 57 Me CF3 HH n-C8H17 58 Me CF3 HH n-C12H25 59 Me CF3 HH CH(CH3)C6H13 60 Me CF3 H Me n-C8H17 61 Me CF3 HH vinyl 62 Me CF3 HH al lyI 63 Me CF3 HH propargyI 64 Me CF3 H Ph Ph 65 Me CF3 H c-Hex Ph 66 Me CF3 H Ac Ph 67 Me CF3 H 0丫iPr Ph 68 Me CF3 H Bz Ph 69 Me CF3 H CoiPr Ph 70 Me CF3 H COOMe Ph 71 Me CF3 H COOPh Ph 72 Me CF3 H S02Me Ph 73 Me CF3 H S02Ph Ph 74 Me CF3 H CONHMe Ph 75 Me CF3 H C0NMe2 Ph 76 Me CF3 H CONHiPr Ph 77 Me CF3 H CONHPh Ph 79 Me CF3 H Me 0 Ph 80 Me CF3 H Ό Me 0 81 Me CF3 Cl CF„ Cl Me 0 Ph 24 200916444 [Table 5] Compound No. R 1 R 2 R3 R 6 R7 82 Me CF3 Cl CF Cl Me 0 NC 83 Me CF3 HH Me C00H 84 Me CF3 HH Me Human Me COOH 85 Me CF3 HH Me 'Xj^XMe COOH 86 Me CF3 HH COOH 87 Me CF3 HH COOH 88 Me CF3 HH Me COOH 89 Me CF3 HH Et COOH 90 Me CF3 HH COOH Me 91 Me CF3 HH Ύ&quot; COOH 92 Me CF3 HH COOH 93 Me CF3 HH Me COOMe 25 200916444 [Table 6] Compound No. R 1 R 2 R 3 R 6 R 7 94 Me CF3 HH Me,,Me MeOMOM 95 Me CF3 HH Me COOMe 96 Me CF3 HH \^Me COOEt 97 Me CF3 HH COOEt 98 Me CF3 HH 丫Me COOEt 99 Me CF3 HH Et COOiPr 100 Me CF3 HH COOiPr Me 101 Me CF3 HH vEt COOnPr 102 Me CF3 HH COOnBu 103 Me CF3 H MeS02 Ph 104 Me CF3 H Vcl Ph 105 Me CF3 H Ph 106 Me CF3 H COOiPr Ph 107 Me CF3 H COOBn Ph 108 Me CF3 H C00CH2CF3 Ph 26 200916444 [Table 7] Compound No. R 1 R 2 R3 R 6 R 7 109 Me CF3 H Human XT Ph 110 Me CF3 H Human Ph 111 Me CF3 H 0,,,P Ph 112 Me CF3 H O7 ά;&gt; 113 Me CF3 H S02Ph 114 Me CF3 H S02Ph Me 115 Me CF3 H S02PH X 116 Me CF3 H S02Ph XJ ' 117 Me CF3 H S02Ph 118 Me CF3 H S02Ph jX 119 Me CF3 H cf'o Ph 120 Me CF3 H oA) Ph 121 Me CF3 H S02n-Bu Ph 27 200916444 [Table 8] Compound No. R 1 R 2 R3 R 6 R7 122 Me CF3 H S02Ph 123 Me CF3 H S02Ph n-Bu 124 Me CF3 H S02Ph Bn 125 Me CF3 H S02 Bn Ph 126 Me CF3 H S02Ph n- Hex 127 Me CF3 H S02Ph MeO IVL 128 Me CF3 H S02Ph 129 Me CF3 H S02n-0ct Ph 130 Me CF3 H S02n-Bu n-Oct 131 Me CF3 HH n-Hex 132 Me CF3 HH n-Dec 133 Me CF3 HH n-Hep 134 Me CF3 HH n-Non 135 Me CF3 H S02Ph XT2 136 Me CF3 H S02Ph jT 137 Me CF3 HH He Me ^&quot;COOEt 138 Me CF3 HH 9 ',COOMe 139 Me CF3 HH Me Me •^^COOMe 140 Me CF3 HH Me ^k^COOEt 141 Me CF3 H S02PH ~0~Me 142 Me CF3 H S02Ph _hO_ci 143 Me CF3 H S02Ph n-C8H17 28 200916444 [Table 9]

Compound No. R 1 R2 R3 R8 R 9 R 1 0 144 Me CF3 HHH Me 145 Me CF3 H Me HH 146 Me CF3 HHH c-Hex 147 Me CF3 HHH Allyl 148 Me CF3 HHH Propargyi 149 Me CF3 H Me HH 150 Me CF3 HHH Ph 151 Me CF3 H Ph HH 152 Me CF3 HH Me Ph 153 Me CF3 HH -(CH2) 5- 154 Me CF3 HH -(CH2)2-0-(CH2) 2- 155 Me CF3 H Ac H Ph 156 Me CF3 H Bz H Ph 157 Me CF3 HH Ac Ph 158 Me CF3 HH Bz Ph 159 H CF3 HHH Me 160 H CF3 HHH c-Hex 161 H CF3 HHH Ph 162 Me CF3 Cl HH Ph 163 Me CF3 N02 HH Ph 164 Me CF3 CN HH Ph 165 Me CF3 Me HH Ph 166 Me CF3 OMe HH Ph 167 Me CF3 S02Me HH Ph 168 Et CF3 HHH Me 169 Et CF3 HHH c-Hex 170 Et CF3 HHH Ph 171 i-Pr GF3 μ HH Me 172 i-Pr CF3 HHH c-Hex 173 i-Pr CF3 HHH Ph 174 Me n-C3F7 HHH Me 175 Me n-C3F7 HHH Ph 176 Me i-C3F7 HHH Me 177 Me i-C3F7 HHH Ph 29 200916444 [Table 10]

Compound No. R 1 R 2 R3 R8 R 9 R 1 0 178 Me CF3 HHH cf3 \ Me 179 Me CF3 HHH CN 180 Me CF3 HHH &gt;&gt; 181 Me CF3 HHH Me 182 Me CF3 HH COOMe Ph 183 Me CF3 HH COOPh Ph 184 Me CF3 HH S02Me Ph 185 Me CF3 HH S02Ph Ph 186 Me CF3 uu GONHMe Ph 187 Me CF3 H Ph CONHPh H 188 Me CF3 HHHX) 189 Me CF3 HHH XTMe 190 Me CF3 H XrMe HH 191 Me C'F3 jCT 192 Me CF3 H XT HH 30 200916444 [Table 11] Compound No. R 1 R 2 R3 R8 R 9 R 1 0 193 Me CF3 HHH Bz 194 Me CF3 HH Ph Ph 195 Me CF3 HHH CONHPh 196 Me CF3 H Me H f3c 197 Me CF3 HHH FsQ W lie 0 198 Me CF3 HHH ^aCN 199 Me CF3 HH S02Ph f3c w fie 0 200 Me CF3 HH Me Me 201 Me CF3 H Bz Bz Ph 202 Me CF3 H Ac Ac Ph 203 Me CF3 l_j u -G(C02Me)=CH -CH=CH-204 Me CF3 HHH 3 205 Me CF3 HHH 206 Me CF3 HH h 207 Me CF3 HH - (CH2)5- 31 200916444 [Table 12] Compound No. 値3 Ή NMR (CDCI3) δ 0.89 (3Η, t, ^6.8Ηζ), 1.24-1.45 (10H, m), 1.71-1.78 (2H, m), 4.23 (3H, s), 4.31 (2H, t, 〇ί= 6.8Ηζ), 7.07 (1H, s). 4 Ή NMR (CDCI3) &lt;5 1.29-1.49 (4H.m), 1.52-1.62 (2H, m), 1.76-1.80 (2H.m), 1.91-1.96 (2H, m), 4.23 (3H, s), 4.97-5.04 (1H. m), 7.07 (1H, s). 7 'HNMR (CDCg &lt;5 4.28 (3H, s), 7.17-7.24 (2H, m), 7.29-7.32 (2H, m), 7.43-7.48 (2H, m). 8 Ή NMR (CDCI3) δ 4.01 (3H, s), 4.25 (3H, s), 5.35 (2H, s), 6.56 (1H, s), 7.08 (1H, s)_ mp: 75.2-77.6°C 9 Ή NMR (CDCI3) δ 2.48 (3H, s), 4.29 (3H, s), 6.23 (1H, s), 7.35 ( 1H, s). mp: 31-33°C 10 Ή NMR (CDCI3) 6 4.29 (3H, s), 7.17 (1H, d, 〇/=7.3Ηζ), 7.32-7.35 (2H, m), 7.86- 7.91 (1H,m), 8.48(1 H,m) mp: 58.4-60.8°C 11 1H NMR (CDCI3) δ 4.30 (3H, s), 7.37-7.40 (2H, m), 8.82 (2H, d, l/=4.9Hz) 22 Ή NMR (CDC!3) &lt;5 0.88 (3H, t, u/=6.8Hz), 1.26-1.41 (2H, septet, J =7.3Hz), 1.50-1.60 (16H, m), 1.71-1.78 (2H. quint., J = 6.8 Hz), 4.24 (3H, s), 4.31 (2H, t, J = 6.8 Hz), 7.07 (1H, s). 23 'HNMRCCDCIj) δ 2.49 (3H. s), 4.19 (3H. s), 7.14 (1H, s). 57 Ή NMR (CDCI3) δ 0.88 (3H, t, t/=6.8Hz), 1.28-1.35 (10H, m), 1.60 (2H, m), 3.40 (2H, m), 4.21 (3H, s), 6.03 (1H, br-s), 6.73 (1H, s). 58 Ή NMR (CDCI3) δ 0.88 (3H, t, ^7.3Hz) , 1.20-1.35 (20H, m), 3.38-3.43 (2H, m), 4.22 (3H, s), 5.99 (1H, br-s), 6.73 (1H, s). 59 Ή NMR (CDCI3) δ 0.88 (3H, t. ^7.3Hz), 1.23 (3H, d, ^6.3Hz), 1.24-1.35 (8H. m), 1.49-1.53 (2H, m), 4.09-4.14 (1H, m), 4.21 ( 3H, s), 5.77 (1H, br-d, Jt8.3Hz), 6.72 (1H, s). 60 Ή NMR (CDCI3) (5 0.85-0.92 (3H, m), 1.20-1.30 (10H, m) , 1.55-1.70 (2H, m), 3.08 (3H, s), 3.37 (1H, t, 〇fc7.3Hz), 3.52 (1H, t, ^7.3Hz), 3.99 (3H x 1/2, s) , 4.02 (3H x 1/2, s), 6.54 (1H x 1/2, s), 6.59 (1H x 1/2, s). 61 Ή NMR (CDCI3) δ 4.20 (3H, s), 5.16- 5.26 (2H, m), 5.84-5.90 (1H, m), 6.93 (1H, s). 32 200916444 [Table 13] Compound number physical properties '64 'HNMRCCDCIs) &lt;5 4.18 (3H, s), 5.80 (1H , s), 6.69-7.40 (10H, m). mp: 119-1213⁄4 66 Ή NMR (CDCI3) δ 2.45 (3H, s), 4.17 (3H, s), 6.20 (1H, s), 7.15-7.17 ( 2H. m), 7.38-7.47 (3H, m). 69 Ή NMR (CDCI3) (5 1.23 (6H, d, ^6.8Hz), 3.04 (1H. m), 4.16 (3H, s), 6.35 (1H .s) , 7.15 (2H, m). 7.42-7.46 (3H, m). mp: 84-88°C 70 'H NMR (CDCI3) 6 3.78 (3H, s), 4.15 (3H, s\ 6.61 (1H, s ), 7.21 (2H, m), 7.44 (3H, m). 71 1H NMR (CDCI3) 6 4.18 (3H, s), 6.76 (1H, s), 7.05 (2H, m), Ί.22-1.52 ( 8H, m). 73 Ή NMR (CDCI3) δ 4.07 (3H, s), 5.73 (1H, s), 7.25 (2Hr m), 7.44-7.60 (5H, m), 7.69 (1H, m), 8.01 ( 2H, m). mp: 149.6-151.2°C 82 Ή NMR (CDCI3) δ 4.14 (6H, s), 7.41 (1H, d, ^7.8Hz), 7.60 (1H, t, J=7.8Hz), 7.70 -7.72 (1H, m), 7.79 (1H, d, 6.3 Hz). 83 Ή NMR (CDCI3) 6 1.0K3H, d, ι/=6·8Ηζ), 1.03(3H, d, J=T.3Hz ), 2.32(1 H, m), 4.20OH, s), 4.62 (1 H, dd, ^8.3Hz, 4.9Hz), 7.03(1 H, s), 7.19(1 H, d, jt8.3Hz) Mp: 143.2-145.6°C 93 Ή NMR (CDCI3) 5〇.98(3H,d, 夕7.3Hz), 1.01(3H, d, Α6.8Ηζ), 2.2X1H, m), 3.80(3H, s ), 4.20(3H, s), 4.69(1 H, dd, ufc8.3Hz, 4.9Hz), 6.53(1 H, d, ^8.3Hz), 6.86(1 H, s). mp: 60.4~62.0° C 94 Ή-NMR (CDCI3, ppm): 0.98 (3H, d, .A6.83HZ), 1.01 (3H, d, J = 6.83Hz) 2.27 (1H, m), 3.80 (3H, s), 4.20 ( 3H, s), 4.69 (1H, dd, ^4.88Hzt 8.78Hz), 6.56 (1H, d, ut8.29Hz), 6.87 (1H, s) mp: 58.8-61.2°C 96 Ή-NMR (CDCI3, ppm): 1.32 (3H, t, cA7.32Hz), 1.52 (3H, d , ιΛ7.32Ηζ), 4.20 (3H, s), 4.26 (2H,q, ut7.32Hz), 6.74 (1H, d, J=6.83Hz), 6.85 (1H, s) mp:68.8-70.8°C 103 NMR NMR (CDCI3) δ 3.52 (3H, s), 4.23 (3H, s), 5.75 (1H, s), 7.30-7.33 (2H, m). 7.46-7.52 (3H, m). 33 200916444 [Table 14 】

Compound number 値 104 Ή NMR (CDCI3) δ 4.15 (3Η, s), 6.50 (1H, s), 7.16 (2H, d. c^6.8Hz), 7.36-7.43 (5H, m), 7.68 (2H. d, ^6.8Η2). 105 Ή NMR (CDCI3) 6 2.37 (3H, s), 4.13 (3H, s), 6.54 (1H, s), 7.16-7.20 (4H, m), 7.32-7.43 (3H, m), 7.64 (2H.d, ^8.3Hz). 106 Ή NMR (CDCI3) 6 1.16 (dH, 6.3), 4.14 (sH), 4.95-5.02 (mH. m), 6.66 (sH). 7.21-7.23 (mH, m), 7.40-7.47 (mH.m). 107 Ή NMR (CDCI3) δ 4.07 (3H, s), 5.17 (2H, s), 6.57 (1H, s), 7.15-7.21 (3H, m ), 7.32-7.45 (7H, m). 108 Ή NMR (CDCI3) δ 4.17 (3H, s), 4.55 (2H, q. Vwf=8.3Hz), 6.64 (1H, s), 7.22-7.25 (2H, m), 7.41-7.50 (3H, m). 109 'H NMR (CDCI3) δ 4.19 (3Hr s), 6.71 (1H, s) ( 7.31-7.34 (4H, m), 7.45-7.52 (3H? m) 110 Ή NMR (CDC!3) δ 2.32 (3H, s), 4.18 (3H, s), 6.76 (1H, s), 6.91 (2H, d, ^8.3Hz), 7.15 (2H, d, ui= 8.3Hz), 7.33-7.36 (2H.m). 7.44-7.52 (3H, m). 111 1H NMR (CDCI3) 5 4.09 (3H, s), 5.76 (1H, s), 7.22 (2H, d, jf =7.8Hz), 7.44-7.56 (5H, m), 7.94 (2H, d, ^=7.8Hz). 112 Ή NMR (CDCI3) δ 4.14 (3H, s), 4.68 (2H , br-s), 6.23 (1H, br-s), 6.34-6.36 (1H, m), 7.19 (1H, s), 7.54 (1H, s), 8.04 (1H, br-s), 8.12 (1H , br-s), 8.20 (1H, br-s). 113 1H NMR (CDCI3) δ 2.26 (3H, s), 4.09 (3H, s), 5.44 (1H, s), 7.16 (1H, d, J =7.3Hz), 7.29-7.72 (6H.m). 8.14 (2H, d, t/=7.3Hz). Λ Λ r* Λ Λ Λ mp; οο.ο a u 114 Ή NMR (CDCI3) δ 2.20 ( 6H, s), 4.12 (3H, s), 5.32 (1H, s), 7.17 (2H, d, J=7.8Hz), 7.33 (1H, t, J=7.8Hz), 7.60 (2H, t. J =7.8Hz), 7.70-7.74 (1H.m), 7.26 (2H, d, J = 7.8Hz). mp; 138.0-140.0°C 115 1H NMR (CDCI3) δ 4.04 (3H, s), 5.83 (1H , s), 7.37 (1H, s), 7.43-7.49 (2H, m), 7.58 (2H, t, l/=7.8Hz), 7.69-7.72 (2H, m), 8.10-8.12 (2H, m) 116 Ή NMR (CDCI3) δ 4.08 (3H, s), 5.86 (1H, s), 7.37 (2H, d, l/=7.8Hz), 7.59 (2H, t, J = 7.8Hz), 7.71-7.74 (3H.m), 7.98 (2H, d, J=7.8Hz). mp; 143.4-146.0°C 117 Ή NMR (CDCI3) δ 4.08 (3H, s), 5.92 (1H, s), 7.36 (2H, d, ./=7.8Ηζ), 7.59 (2H.t, J = 7.8Hz), 7.72-7.77 (3H, m), 7.95 (2H, d, 〇/=7.8Hz). mp; 178.8-181.2°C 34 200916444 [Table 15]

Compound No. 値118 1H NMR (CDCI3) δ 2.52 (3Η, s), 4.07 (3H, s), 5.89 (1H, s), 7.10-7.13 (2H, m), 7.25-7.28 (2H, m), 7.56 (2H, t, J=l.8Hz), 7.69 (1H, t, J = 7.8Hz), 8.01 (2H, d, J = 7.8Hz). mp; 180.4-181.2°C 119 Ή NMR (CDCI3) δ 3.91 (3H, s), 4.08 (3H, s), 5.72 (1H, s), 7.01 (2H.d, .;=7.8Ηζ), 7.22 (2H, d, 7.43-7.51 (3H, m), 7.96 (2H, d. J=T.8Hz). mp; 149.6-155.2°C 120 1H NMR (CDCI3) δ 4.09 (3H, s), 5.78 (1H, s), 7.22-7.25 (2H, m), 7.48 (2H, t, J = 7.8 Hz), 7.54 (1H, t, J = 1.8 Hz), 7.57 (2H, d, J = 7.3 Hz), 8.12 (2H, d, J = 7.3 Hz). mp; 164.4-195.2°C 121 Ή NMR (CDCI3) δ 0.99 (3H, t, l/=7.8Hz) I 1.0-1.56 (H. m), 1.92-1.95 (2H, m). 3.74-3.78 (2H, m ), 4.22 (3H. s), 5.63 (1H, s), 7.33 (2H, dd., /=1.5, 7.8Hz), 7.47-7.52 (3H, m). mp; 108.8-110.4°C 122 Ή NMR (CDCI3) S 4.05 (3H, s), 5.92 (1H, s), 7.52 (1H, dd. J=A.8, 7.8Hz). 7.59 (2H, t, J=7.8Hz), 7.74 (1H, t, JsISHz), 8.05 (2H, d, JsT.BHz), 8.17 (1H, dd, J = 1.5, 7.8Hz), 8.49 (1H, dd, J=1.5, 4.8Hz). mp; 119.2-120.03⁄4 123 1H N MR (CDCI3) δ 0.95 (3H, t, J=7.3Hz), 1.24-1.40 (3H, m), 1.72-1.77 (3Hr m), 3.77 (3H, s), 3.92-3.96 (2H, m), 6.56 (1H, s), 7.52-7.56 (2H, m), 7.65 (1H, t, J _irtll \ -1 &quot;Ί Λ /ΛΙ 1 1 1 ! ---i f- -1 rn 1 \ -/. On B/./h, B π, αα, l/- i_o, 八门ζλ 124 Ή NMR (CDCI3) &lt;5 3.64 (3Η, s), 5.15 (2H, s), 6.52 (1H, s ), 7.18-7.35 (5H, m), 7.48-7.66 (5H, m). mp; 110.4-111.6°C 125 Ή NMR (CDCI3) c5 4.26 (3H, s), 5.05 (2H, s), 5.30 ( 1H, s), 6.46 (2H, dd, ./=1.5, 7.8Hz), 7.22 (2H, t, J=7.8Hz), 7.36-7.50 (6H, m). mp; 146,0-147.6°C 126 1H NMR (CDCI3) δ 0.83-0.90 (3H, m), 1.22-1.31 (6H, m), 1.74-1.78 (2H, m), 3.78 (3H, s), 3.91-3.95 (2H. m). 6.56 (1H, s). 7.52-7.55 (3H; m), 7.65-7.76 (2H: m). 127 Ή NMR (CDCQ &lt;5 3.53 (3H, s), 3.98 (3H, s), 6.04 (1H , s). 7.09 (1H, dd, J=5, 3. 7.3Hz), 7.56 (2H, t, l/=7.8Hz), 7.67-7.71 (1H, m), 7.91 (1H, dd, J= 2.0, 7.8 Hz), 7.99 (2H, dd, J=1.5, 7.3 Hz), 8.21 (1H, dd, i/=1.5, 5.3 Hz). mp; 135.6-138.8°C 35 200916444 [Table 16] Compound numberPhysical properties 1 128 1H NMR (CDCI3) δ 3.86 (3Η, s), 4.07 (3H, s), 5.82 (1H, s), 6.94 (2H, dd, J=2.0, 6.8Hz), 7.12 (2H, dd, J=2.0, 6.8Hz), 7.58 (2H, t, v/=7.8Hz), 7.72 (1H, t, ,/=7.8Hz), 8.01 (2H, d, ι;=7.8Ηζ). 129 Ή NMR (CDCI3) δ 0.88 (3H, t, cy=7.3Hz), 1.27-1.50 (10H, m), 1.93-1.97 (2H, m), 3.72-3.76 (2H, m), 4.22 (3H, s), 5.63 (1H, s), 7.30-7.32 (2H, m), 7.46-7.52 (3H, m). mp; 102.0-103.2°C 130 Ή NMR (CDCQ &lt;5 0.87 (3H, t, J=6.8Hz) ), 0.97 (3H, t, l/=7.3Hz), 1.25-1.29 (10H, m), 1.46-1.52 (2H, m), 1.67-1.69 (2H, m), 1.80-1.85 (2H, m) , 3.49 (2H, t, J=7.8Hz), 3.82 (2H, t, t/=7.8Hz), 4.05 (3H, s), 6.76 (1H, s). mp; 59.8-61.0°C 131 1H NMR (CDCI3) δ 0.88 (3H, t, , /^β.βΗζ), 1.24-1.34 (6H, m), 1.56-1.62 (2H, m), 3.40 (2H, dd, J=6.3, 6.8Hz), 4.22 (3H, s), 5.99 (1H, br-s), 6.73 (1H, s). 132 Ή NMR (CDCI3) δ 0.88 (3H, t, J=6.8Hz), 1.24-1.34 (14H, m) , 1.56-1.63 (2H, m), 3.38-3.43 (2H, m), 4.22 (1H, s), 5.99 (1H, br~s), 6.73 (1H, s). 133 Ή NMR (CDCI3) δ 0.89 (3H, t, l/=7.3Hz), 1.24-1.36 (8H, m), 1.54-1.62 (2H, m), 3.38-3.43 (2H, m), 4.21 (3H, s), 6.00 (1H, br-s), 6.73 (1H, s). 134 Ή NMR (CDCI3) δ 0.88 (3H, t, J=7.3Hz), 1.24-1.36 (12H, m), 1.56-1.63 (2H, m), 3.38-3.43 (2H, m), 4.21 (3H, s), 6.00 (1H, br-s), 6.73 (1H, s). 135 Ή NMR (CDCI3) δ 4.09 (3H, s), 5.99 (1H, s), 7.44 (2H, dd, J=2.0, 6.8Hz), 7.59 (2H, t, J=7.8Hz), 7.72-7.74 (1H, m), 7.95 (2H, dd, ./=1.5, 7.8Hz), 8.32 (2H, dd, J =2.0, 6.8Hz). mp; 155.5-156.6°C 136 1H NMR (CDCI3) δ 4.07 (3H, s), 5.83 (1H, s), 7.13-7.24 (4H, m), 7.59 (2H, t, J = 7.8 Hz), 7.72 (1H, t, J=7.8Hz), 7.99 (2H, d, l/=7.8Hz). mp; 116-116.8°C 137 1H-NMR (CDCI3, ppm): 0.98 (3H, d ^6.83Hz), 1.01 (3H, d, ./:6.83Hz) 1.32 (3H, t, jt6.83Hz)f 2.28 (1H, m), 4.20 (3H, s), 4.26 (2H, m), 4.67 (1H, m), 6.60 (1H, d, ut8.29Hz). 6.87 (1H, s) m.p_: oil 138 Ή-NMR (CDCI3. ppm): 3.78 (3H, s), 4.17 ( 3H, s), 5.67 (1H, d, υ&lt;=6.83Ηζ), 6.90 (1H, s), 7.11 (1H, d, 〇t6.43Hz), 7.34-7.42 (5H, m) mp: semi-solid 36 200916444 [Table 17]

Compound No. 値 139 Ή-NMR (CDCI3i ppm): 1.67 (6H, s). 3.80 (3H, s), 4.19 (3H, s). 6.71 (1H. br-s), 6.80 (1H, s) mp 112.8-114.8°C 140 Ή-NMR (CDCI3. ppm): 1.27-1.34 (6H, m), 2.61 (2H. m), 4.18 (2H. m). 4.22 (3H, s), 4.49 (1H. m 6.78 (1H, s), 7.05 (1H, d, J = 8.29Hz) m.p_: oil 141 Ή-NMR (CDCI3 ppm): 2.42 (3H, s), 4.06 (3H, s), 5.79 (1H, s). 7.11 (2H, dd, 41.95Hz, 6.34Hz), 7.25 (2H, d, Jt8.29Hz), 7.56 (2H, m), 7.70 (1H, m), 8.01 (2H, m ) mp: 126.4-129.6 ° C 142 Ή-NMR (CDCI 3. ppm): 4.07 (3H, s), 5.90 (1H. s), 7.17 (2H. m). 7.43 (2H, m), 7.57 (2H, m). 7.71 (1H,m), 7.97 (2H.m) mp:124.8-127.6°C 143 Η-NMR (CDCI3. ppm): 0.88 (3H, t, J=7.32Hz), 1.21-1.30 (10H , m), 1.76 (2H. t, 〇fc7.32Hz). 3.78 (3H, s), 3.93 (2H, t, ^7.81 Hz). 6.56 (1H, s), 7.54 (2H, m), 7.67 ( NMR: NMR (CDCI3) δ 3.43 (3H, s) s), 8.13 (1Hr s). 145 NMR (DMSO-4) δ 3.17 (3H, s), 3.93 (3H, s). 5.02 (2H, s), 7.00 (1H, s). 146 Ή NMR (CDCI3) δ 1.00-2.00 (10H, m), 4.04 (1H, m), 4.11 (3H, s), 6.63 (1H, s), 6.87 (1H, s), 8.20 (1H , s). 150 Ή NMR (CDCI3) 5 4.21 (3H, s), 6.20 (1H, br-s like), 6.89 (2H, d, l/=8.3Hz), 6.99 (2H, t, J=7.3 Hz), 7.26-7.28 (1H, m). 151 NMR (CDCI3) δ 4.15 (3H, s)t 4.50 (2H, br-s like), 7.21-7.26 (2H, m), 7.35-7.40 (3H. m). 152 Ή NMR (CDCI3) 6 3.30 (3H, s). 4.24 (3H, s), 6.87-6.95 (4H, m), 7.27 (1H, t, J = 7.3Hz), 7.81 (1H, br - s). 154 Ή NMR (CDCI3) δ 2.94 (4H, m), 3.86 (4H, m), 4.22 (3H. s), 6.77 (1H, s). 6.90 (1H, br-s). m_p. : 152-154〇C 156 Ή NMR (CDCI3) δ 4.19 (3H, s), 7.01 (1H, s), 7.19-7.48 (10H, m), 9.27 (1H, br-s). 182 ^ NMR (CDCI3 δ 3.84 (3Ht s)F 4.21 (3H, s), 6.93 (1Hf s)f 7.27-7.45 (5H, m)t 8.60 (1Hr br-s). 37 200916444 [Table 18] Compound No. 値 188 Ή NMR (CDCI3) δ 4.20 (3Η, s), 6.75 (1H, d, =8.3Hz), 6.86 (1H, dd, J =6.8, 8·3Ηζ), 7.00 (1H, s), 7.20 (1H, br -s), 7.56 (1H, dd, 7=4.8, 6.8Hz), 8.17 (1H, d, J = 4.8Hz). 189 Ή NMR (CDCI3) 6 2. 27 (3H, s), 4.20 (3H, s), 6.18 (1H, br-s), 6.79 (2H. d, J = 7.8Hz), 6.92 (1H, s), 7.06 (2H, d, u/ = 7.8 Hz), 8.04 (1H, br-s). 190 1H NMR (CDCI3) δ 2.37 (3H, s), 4.13 (3H, s), 5.80 (2H, br-s), 7.08-7.26 (5H, m). 191 Ή NMR (CDCI3) δ 4.21 (3H, s), 6.18 (1H, br-s), 6.82 (2H, d. ./=8^2), 6.94 (1H, s), 7.23 (2H , d, J=8.8Hz), 7.82 (1H, br-s). 192 Ή NMR (CDCI3) 6 4.14 (3H( s)r 4.88 (2Hf br-s)( 7.17-7.20 (3Hf m), 7.34- 7.38 (2H, m). 193 'H NMR (CDCI3) δ 4.24 (3H, s), 7.35 (1H, s), 7.47 (2H, t, J=7.3Hz), 7.49 (1H, t, J = 7.3 Hz), 7.95 (2H, d, J=T.3Hz), 9.90 (1H, br^s). 10.6 (1H, br-s). 194 Ή NMR (CDCI3) δ 4.23 (3H, s), 6.94 ( IH, s), 7.00-7.37 (10H, m), 8.18 (1H, s). 195 Ή NMR (CDCI3) 6 4.19 (3H, s), 7.01 (1H, t, J = 7.8Hz), 7.25-7.33 (3H, m). 7.43 (2H, tW=7.8Hz), 7.97 (1H, s), 8.37 (1H, s), 10.15 (1H, s). mp:224.8-226.0 196 Ή NMR (CDCI3) 6 3.55 (3H, s), 3.97 (3H, s), 4.14 (3H, s), 6.72 (1H, s), 6.87 (1H, s), 8.25 (1H, s) mp: 246.0-248.0; 197 Ή NMR ( CDCI3) δ 4.24 (6H, s), 6.98 (2H, s), 8.42 (2H, s). 198 Ή NMR (CDCI3) δ 4.22 (3H, s), 6.38 (1H, s), 6.92 (2H, d, J=8.8Hz), 6.98 (1H, s), 7.56 (2H , d, J=8.8Hz), 7.86 (1H, s). 199 NMR (CDCIj) δ 4.00 (3H, s), 4.08 (3H, s), 6.81 (1H, s), 7.08 (1H, s) , 7.62 (2H, t, 7.75 (1H, t, u/= 7.8 Hz), 8.13 (2H, d, l/= 7.8 Hz), 9.14 (1H, br-s). 200 Ή NMR (CDCI3) δ 2.71 (6H, s), 4.22 (3H, s), 6.72 (1H, br-s). 201 1H NMR (CDCI3) δ 3.72 (3H, s), 6.65 (1H, s), 7.08-7.71 (15H, m 202 Ή NMR (CDCIj) δ 2.05 (3H, s), 2.57 (3H, s), 3.84 (3H, s), 6.86 (1H, s), 7.01-7.03 (2H, m), 7.39-7.40 ( 3H, m) 203 Ή NMR (CDCI3) S 1.33 (3H, t, J=7.3Hz), 4.23 (3H, s), 4.26 (2H, q, J=7.3Hz), 6.26 (1H. dd, J= 2.5, 4.0 Hz), 7.00 (1H, dd, J=1.5, 4.0 Hz). 7.05 (1H. s), 7.18 (1Hr dd, J = 1.5, 2.5Hz), 9.60 (1H, br-s). 38 200916444 [Table 19]

Compound No. 値204 Ή NMR (CDCI3) 6 4.22 (3H, s), 6.66 (1H, br^TeaTTTirT~~---- s), 7.06 (1H, d. J=7.8Hz), 7.12 (1Hf t ^/=7.8^), 7.8B Πμ ' ' 〇H&gt; 205 fH NMR (CDGI3) 4.22 (3H, s), 6.21 (1H, -- 6.99 (2H, m), 7.31 (1H, d, J= 8.3Hz), 7.93 (1H, br-s). 1 Z)t 6*97' 206 Ή NMR (CDCI3) δ 4.15 (3H, s), 4.82 (2H. -- =7.3HZ), 7.41-7.46 s ) 6·^ (1H. S), 7.04 (1H, d, ^ 207 Ή NMR (CDCI3, PPm): 1.45 (2H, m),].75 (1H, s), 6.85 (1H, br-s ) WH, s)· 6 75 mp: 195.2-196.4°C

[Formulation Example and Test Example] The formulation examples and the bactericidal activity test examples of the present invention are exemplified below. By "parts" means "parts by weight". ^ (Formulation Example 1) &lt;granules&gt; 100 parts of 30 parts of compound No. 57, 22 parts of bentonite, π parts of talc, 3 parts of Sorpol 5060 (surfactant; manufactured by Toho Chemical Co., Ltd. and a small amount The foaming agent is kneaded in a granular shape by a basket granulator and dried to obtain a granule (Formulation Example 2) &lt;granules&gt; 15 parts of compound No. 73, 60 parts of bentonite, 21 parts of talc, After mixing 1 part of sodium dodecylbenzene sulfonate, 1 part of polyoxyethylene alkyl aryl ether and 2 parts of sodium lignin sulfonate, add appropriate amount of water and knead it, and make it into a granule by a basket granulator. After drying, 10 parts of granules were obtained. (Formulation Example 3) &lt;Wettable powder&gt; 50 彳7? compound was compounded with 5 143 compounds, 40 parts of carbonic acid mother, 5 parts s〇; rp〇l 5039 (anion a mixture of a surfactant and a white carbon black; a Japanese Pharmacy Co., Ltd., a 5 quot; σ mouth name) and a 5-white anaesthetic black uniformly mixed and pulverized to obtain a wettable powder. (Formulation Example 4) &lt;Wet WP &gt; 39 200916444 30 parts of compound number 194, 63 parts of high genus, 5 parts of Sorpol 5039 (anionic surfactant and white carbon black mixed (Compound product made by Japan Toho Chemical Co., Ltd.) and 2 parts of white carbon black are uniformly mixed and pulverized to obtain a wettable powder. (Formulation Example 5) &lt;Emulsion&gt; 20 parts of compound No. 3, 55 parts of two Toluene, 2 parts of dimethylformamide, 5 parts of Sorpol 2680 (surfactant; trade name of Toyo Chemical Co., Ltd., Japan) were uniformly mixed to obtain an emulsion. (Formulation Example 6) &lt;Aqueous suspension&gt; Sorpol 3353 (non-ionic surfactant; trade name manufactured by Toho Chemical Co., Ltd.), 5 parts of 1% aqueous solution of Sanxianjiao, 4 parts of water, 1 part of ethylene glycol, and 40 parts of compound The compound of No. 23 was stirred and then wet-pulverized by a sand mill to obtain an aqueous suspension. (Formulation Example 7) &lt;Powder&gt; 5 parts of the compound of Compound No. 70 and 95 parts of dry soil were mixed to obtain a powder. (Test Example 1) &lt;Rice rice fever control effect test (spray test)&gt; A dilution of a wettable powder having a compound concentration of 25 〇ppm prepared according to Formulation Example 4 was sprinkled on rice seedling pots. (Variety: Koshihikari; 2 leaf stage) and ^ ΐ, this seedling Put into the artificial meteorological room (setting conditions: 22. 〇, 12 hours light and dark cycle), spray inoculation with the spore suspension of rice fever bacteria. Secondly, the artificial meteorological room maintains a high humidity state, and investigates the disease of the seedling after 7 days of vaccination. The number of plaques was calculated according to the following formula: ° Control rate (%) = (1 - number of lesions in the treatment area / number of lesions in the untreated control area) χ 1 〇〇 results showed that the following compounds showed a rate of 80 or more. Compound Nos.: 8, 57, 107, 109, 11 〇, 15 〇, 151, 152, 182, 189, 204, 205 On the other hand, the following comparative compounds are described in the following Japanese Patent Publication No. Hei 2-129171, the following structure The same test results were carried out, and the control rate was less than 8〇. 200916444

The above structure and the hair

Light; 3 leaf stage) perfusion treatment. After 3 weeks of perfusion treatment, the cultivar 1 was spray-inoculated with rice scorpion core liquid of rice blast fungus, and placed at the temperature of 25 ° C under high humidity conditions, and the number of lesions was investigated. The control rate was calculated according to the following formula. Control rate (%) = (1 - number of lesions in the treatment area / number of lesions in the untreated control area) χ 100 Results The following compounds showed a rate of prevention of more than 8〇. Compound Nos.: 2, 3, 4, 7, 8, 9, 10, 〖1, 22, 23, 57, 58, 6b 68, 69, 70, 73, 82, 83, 93, 94'96, 103, 106, 107, 1, 8, 111, 112, 122, 127, 142, 143, 145, 146, 150, 151, 154, 160, 182, 188, 189, 190, 19, 192, 193, 194, 195, 196, 200, 201, 202, 203, 204, 205, 206, 207 On the other hand, the same test results were carried out with the following comparative compounds (described in Japanese Patent Laid-Open No. Hei 2-129171, the following structural formula), and the control rate was not reached. 50.

CF NC 41 200916444 · The above structure and the combination of the above (4) in the same place A is two-year-old, R6 and R7--the hydrogen atom is another - Fang V is a formula 〇) (crystal = 3) < rice rice fever Control effect test (nursing box test) &gt; no will = 1 dose (column 1 prepared into granules, treated with 50g per box of rice seedlings r 3 days later 'transplanted in _ points i public Wagner sisters in rice heat The spore suspension of the pathogen was sprayed and inoculated under the same humidity condition for 1 week, and then the number of lesions was investigated. The X 100 control rate was determined according to the following formula (8) = (1 - number of lesions in the treatment area / number of lesions in the untreated control area) The following compounds exhibited a control rate of 8 〇 or more. Compound No.: 3, 23, 57, 73, ία, 194 Further, the following compounds showed a compound number of 50 or more and less than 8〇: 7 + (Test Example 4) &lt;; tomato late blight control effect test> 1 dissolved in _ compound diluted with water to 25Qppm, in the compound leaves to develop 4 leaves of the Gong seedlings (variety: world one. mother pot 1 〇 mL sprinkle 1). After air drying Move into 18U_12 hours day ^ shield = Phytophthora infestans, travel spore suspension 0f = species. Inoculation after 4 days investigation The incidence of 4 tablets of lobular sputum was in the rate of treatment. The rate was calculated according to the following formula: =1) = (1 - area of diseased area of treatment area / area of diseased area without treatment) The results showed the following compounds 80 The above prevention rate. Compound No.: 204 mouth &gt; (Test Example 5) &lt;Bean bean gray mold control effect test (spray test, 42 200916444 will be prepared according to Formulation Example 4; like dilution solution, 5 〇 every 4 pots = ^ j Wet cotyledon expansion period). To be horrible (ασ种.Green top; prepared conidia suspension (two 5' on the cultivation of Botrytis cinerea, _ Na above = room 2?? species = species in the post-subsidiary ugly disease, bribery, The control rate was calculated according to the following formula: 4 7 days of prevention and control = G - number of lesions in the treatment area / number of lesions in the untreated control area) χ 1〇〇 The following compounds showed a rate of 80 or more. Compound No.: 150, 205 A compound which exhibits a bactericidal agent which is harmful to the acid derivative of the present invention, and which is more excellent in the compound of the present invention than the compound of Japanese Patent Laid-Open No. 2-. 5 Tiger Bulletin [Simplified illustration] None [Main component symbol description] None 43

Claims (1)

200916444 VII. Patent application scope: 1·-species tons of salicylic acid derivatives, in the following general formula (1), R2 R3, general formula (1) represents a hydrogen atom or a carbon atom having 1 to 6 carbon atoms; 1 , self-independent, indicating a hydrogen atom, a carbon atom 1 to 6 alkyl group, carbon atomic octagonal dentate base, alkoxy group having 1 to 6 carbon atoms, carbon atom number 6 group, carbon number 1 to 6 to find sulfur group, carbon number The pyridyl group having 1 to 6 halogenated groups, the toothed calcined carbon having 1 to 6 carbon atoms, the % of the halogenated group having 1 to 6 atomic number, and the number of carbon atoms 1 to 6 'Table is not 0R4, a SR5, - NRY, or -NR8Nr9r10. J- - 3; ^.-. Atomic number 1~6 of the dazzle, can be taken; R5 represents a carbon number of 1~12, a carbon atom having 2 to 6 alkenyl groups having a carbon number of 3 to 6 ring S 3 carbon 6 ^ a heteroaryl group substituted with a carbon atom having 1 to 6 carbon atoms, a square group which may be substituted, or a heteroaryl group which may be substituted; a hydrazine-substituted R7 such as an alkyl group having 5 to 12 carbon atoms; a cycloalkenyl group having 2 to 6 carbon atoms; and a carbon number of 2 to 6; ,: the number of anti-atoms of 1 to 6, or the number of carbon atoms, the number of 2, the number of 1 to 6 At the base time, R6 represents a cesium atom, a carbon atom, a terrestrial earth replaced by a scorpion atomic number of 2 to 6 counties, a carbon number of 3 to 6 ring Cong, a first ^^ 44 200916444 alkynyl group, a substituted heteroaryl group , fluorenyl base, aryl stone yellow base, alkyl amine silk, or aromatic amine county. Earth grade soil, burnt stone xanthine and 'R7, such as ring number of carbon atoms 3~6, can be replaced by oxygen A few bases, ", heart two: take the mountains R, R and R1D each independently' means a hydrogen atom, a number of carbon atoms 丨 ~ 12 alkane, Ϊ ~ carbon number 2 ~ 6 of the rare base, carbon number two 6 generations Green, heteroaryl which can be substituted, base, basal, pyrotechnic, aryl yellow, amine, or aryl amine; but '9 does not contain f, R9 and R1 In the case of hydrogen atoms; and 'R and R1Q can be bonded to each other to form a heterocyclic ring A having a carbon number of 2 to 5, as described in the patent field, the derivative of the baric acid, wherein - 1) R represents a halogenated alkyl group having a carbon number of 丨~6. Among them, a fluorocarbon of one to six, wherein, as described in the second paragraph of the patent application, the t-reactive acid derivative, Ϊ atomic number 1~ 6 filament, R2 is carbon No. 1 4 · If the patent application is difficult to record the fourth (4) mirror derivative, the general formula (1) A is a NR6R7 or -NHNR9R10. 5 · - a method for the manufacture of a t-reductive acid derivative The oxime-based acid derivative described in the above paragraphs 1-4 to 4 includes a process for reacting a compound represented by the following general formula (2) with a compound of the following formula (3): • General (2) 45 200916444 ^ [Formula / two ^ table / age mountain atom or carbon number number of 6 appearance base; only 2 and ruler 3 are independent, the table does not 虱 atom, carbon number! ~6 of the alkyl group, the number of carbon atoms i ~ 6 of the oxy group, carbon K number of 6 of the Azul base, ~ sulfur, carbon atom number of 1 ~ 6 (10) tender fine base, «original The square indicates a tooth having a carbon number of 1 to 6 Α a general formula (3 [wherein, Α represents an OR4, -SR5, -NR6r7, or - 8NRgRl0. A wire of a material, a ring of 3 to 6 carbon atoms) a base group, carbon = 2 to 6 filaments, a cycloalkenyl group having 3 to 6 carbon atoms, and a carbon number of 6; the alkyl group having 1 to 6 carbon atoms which may be substituted by a aryl group may be a substituted square group or a heteroaryl group which may be substituted; a carbonic acid number of 1 to 12, a carbonic acid number of 3 to 6 ring-burning group, a carbon number i~u heart group, and a carbon number of 3~ a cycloalkenyl group of 6 or a heteroaryl group having a carbon number of 9 to fi acetylene, a heteroaryl group substituted with a heteroaryl group substituted with a carbon number of 丨~6, a subgroup which may be substituted, or a substitutable group which may be substituted f represents an alkyl group having 5 to 12 carbon atoms, an alkenyl group having 2 to 6 atomic atoms, a ring having 3 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, and a carbon ς substituted by a county. The carbon base of 1 to 6 or the carbon primitive replaced by the carbon atom of the carbon number When R 6 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or a filler having 2 to 6 carbon atoms, a substituted heteroaryl group, a group, a calcined oxygen, an aryloxy group, a pyrrolyl group, an arylsulfonyl group, an alkylamine carbonyl group, or an arylamine carbonyl group; further, R7 represents a cycloalkyl group having 3 to 6 carbon atoms; When the substituted aryl group and the σ-substituted material group are ', the filament representing a carbon number of 2 to 6 and the number of carbon atoms ^ 46 200916444 ～6, the alkynyl group having 2 to 6 carbon atoms, may be substituted An aryl group, a heteroaryl group which may be substituted, a brewing group, a pyridyl group, an aryloxy group, an anthracene group, an aromatic sulfhydryl group, an acridine group, or an arylamine group; the mountains R8, R9 and R115 are each independently , a hydrogen atom, a carbon atom having a number of 丨~12, a ring thiol group having a stone number of 3 to 6, an alkenyl group having 2 to β carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, and a carbon number 2 to 6 alkynyl, substituted heteroaryl substituted carbonogen 1 to 6 alkyl, substituted aryl, substituted heteroaryl, fluorenyl, alkoxycarbonyl, aryloxycarbonyl , alkanesulfonyl, arylsulfonate , an alkylamine carbonyl group, or an arylamine carbonyl group; however, the case where R8, R9&Rh&gt; are all hydrogen atoms; and 'R9 and R1() may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms] 6. A method for producing a pyrazole carboxylic acid derivative, which comprises producing a pyrazolecarboxylic acid derivative according to any one of the above items (i) to 4, comprising a compound represented by the following general formula (4) and the following general formula: The process of reacting the indicated compound: Wherein R1 represents a hydrogen atom or an alkyl group having a carbon number of i to 6; and hydrazine and p are each independently represented by a hydrogen atom, an alkyl group having a carbon number of 丨6, and a halogenated alkyl group having a carbon number of 丨6. An alkoxy group having 1 to 6 carbon atoms, an alkoxy group having a carbon number of 丨~6, an alkylthio group having 1 to 6 carbon atoms, a toothed alkylthio group having a carbon number of 丨6, and a carbon atom a sulfinyl group having 1 to 6 alkyl groups, a sulfinyl group having 1 to 6 carbon atoms, a sulfonyl group having 1 to 6 carbon atoms, and a halogenated sulfonyl group having 1 to 6 carbon atoms And a halogen atom, a cyano group or a nitro group; but at least one of R2 and R3 is a halogenated alkyl group having a carbon number of i to 6; further, Y is not a leaving group. General formula (3) 47 200916444 [In the formula, A represents a 〇R4, __ QD5 β 7 R4# dry stone ru is the original name 9 SR, - cis R, or a NR8 biliary 9R10; R table does not ash atom number 3~12 The sleek base, the atomic number 2~6 of the thin base, the end piece is not approved Q c is the number 3~6 of the base, the carbon 6 mi l the semantics it" the number of 5~12 filament, the carbon number 2~ 6 Women's Beauty, Stone Mountain Shoulder Number 1 e ·Γ^子子2~6丝丝, 被取取^&quot;的碳&lt;«Ι^Βΐίίί' W mm _子' Carbon number 1~12 a base, a carbon number of 2 to 6 alkenyl groups, a cyclopentene group having 3 to 6 carbon atoms, a disc atomic number of 2 to 6 ', a soil, a heteroaryl group which may be substituted, a mercapto group, an alkoxycarbonyl group, and an aromatic group. An oxycarbonyl group, a aryl sulfonyl group, an alkylamine carbonyl group, or an arylamine carbonyl group; only -1 and, further, R7 represents a cycloalkyl group having 3 to 6 carbon atoms, and a heteroaryl group which may be substituted When R 6 represents an alkenyl group having 2 to 6 carbon atoms, a carbon group having a carbon content of 3:6, a fluorenyl group having 2 to 6 carbon atoms, an aryl group which may be substituted, a heteroaryl group which may be substituted with (10), Sulfhydryl, pyridine, aryloxy, hydrazino, arylalkylamine carbonyl, or arylamine carbonyl; /, - , R8, R9 and yttrium are each independently, and represent a hydrogen atom, a carbon atom number of 丨~12, an alkylene group having an anatomical number of 3 to 6, a ring-burning group having 2 to 6 carbon atoms, and a carbon number of 3 to 6. a cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, a hard group substituted with a heteroaryl group which may be substituted, an alkyl group of 1 to 6, an aryl group which may be substituted, a heteroaryl group which may be substituted, and an anthracene义', alkoxycarbonyl, aryloxycarbonyl, alkanesulfonyl, arylsulfonyl, alkylamine carbonyl, ·&quot;, m-based; however, without r8, R9 and r are hydrogen atoms; Further, 'R9 and hydrazine can be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms;| 7. 7. A fungicide' contains the scope of the patent application No. 1 to 4, which is the item of the product. At least one of the substances is used as an active ingredient. Compared with 48 200916444 8. The bactericide described in claim 7 is characterized by a bactericidal agent for agriculture and horticulture. 49 200916444 IV. Designated representative figure: '(1) Representative of the case Pictured: No picture. (2) Simple description of the symbol of the representative figure: Yiwu. If there is a chemical formula in this case, please reveal the best display invention. Characterized by the chemical formula: κ ~ K