Alpha-aryl-alpha-phenylethyl-1H-1,2,4-triazole-1-propanenitriles.
Abstract
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Expired 1 July 2007, 19.2 years ago.
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27 claims: 8 independent, 19 dependent
- 1【請求項1】式 〔式中、 Zは、エチレン、エテニレン、エチニレン、イソプロピレン、ハロゲン化されたエチレン、ハロゲン化されたエテニレン、またはハロゲン化されたイソプロピレンであり、 Ar(X m )は、置換または非置換のC 6 -C 10 芳香族環構造であり、Ar(Y n )は、置換または非置換のC 6 -C 10 芳香族環構造、または、4個の炭素原子および1個の酸素もしくは硫黄原子を有する5員環、または、1個の窒素原子および5個の炭素原子を有する6員環、または、2個の窒素原子および4個の炭素原子を有する6員環であり、 XおよびYは、独立的に、同じかまたは異っており、かつハロゲン、任意的に3個までのハロゲンで置換された(C 1 -C 6 )アルキル、任意的に3個までのハロゲンで置換された(C 1 -C 6 )アルケニル、ヒドロキシ、(C 1 -C 6 )アルコキシ、(C 2 -C 6 )アルケノキシ、任意的に2個までのハロゲンで置換されたフェニル、シアノ、アミノ、6個までの炭素原子を有するモノアルキルアミノ、各アルキル基に6個までの炭素原子を有するジアルキルアミノ、-C(O)H、(C 1 -C 6 )アルキルスルホニル、アリールスルホニル、および-C(O)NR 1 R 2 (式中、R 1 およびR 2 は、独立に、水素または(C 1 -C 6 )アルキル)から成る群から選ばれ、 Rは、水素、または、任意的に3個までのハロゲン、トリフルオロメチル、もしくは(C 1 -C 6 )アルキルで置換されたフェニルであり、 mおよびnは、独立的に、0~3である〕 を有する化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 2【請求項2】Zは、-CH 2 CH 2 -であり、 Ar(X m )は、任意的に置換されたフェニルまたはナフチルであり、 Ar(Y n )は、任意的に置換されたフェニルであり、XおよびYは、独立的に、同じかまたは異っており、かつハロゲン、トリフルオロメチル、ヒドロキシ、メトキシ、エトキシ、プロポキシ、メチル、エチル、フェニル、およびナフチルから成る群から選ばれ、 mおよびnは、独立的に、0、1、または2である、特許請求の範囲第1項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 3【請求項3】X m は水素、2-ハロゲン、3-ハロゲン、4-ハロゲン、3-トリフルオロメチル、4-トリフルオロメチル、4-メトキシ、4-メチル、4-エチル、および3,4-ハロゲンから成る群から選ばれ、 Y n は水素、2-ハロゲン、3-ハロゲン、4-ハロゲン、2,6-ハロゲン、3-トリフルオロメチル、2-メトキシ、および2-エトキシから成る群から選ばれる、 特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 4【請求項4】X m は、水素である、特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 5【請求項5】Y n は、4-ハロゲンである、特許請求の範囲第4項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 6【請求項6】X m は、4-ハロゲンである、特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 7【請求項7】Y n は、水素または4-ハロゲンである、特許請求の範囲第6項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 8【請求項8】Y n は、2-ハロゲンである、特許請求の範囲第6項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 9【請求項9】Y n は、2-メトキシまたは2-エトキシである、を有する特許請求の範囲第6項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 10【請求項10】X m は、2-ハロゲンであり、Yは、水素または4-ハロゲンである、特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 11【請求項11】X m は、3-ハロゲンまたは4-ハロゲンであり、Y n は、3-ハロゲンである、特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 12【請求項12】X m は、3-ハロゲンであり、Y n は、水素、3-ハロゲン、4-ハロゲン、2-メトキシ、または2-エトキシである、特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 13【請求項13】Y n は、水素または4-ハロゲンである、特許請求の範囲第12項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 14【請求項14】X m は、4-トリフルオロメチルであり、Y n は、水素、4-ハロゲン、2-メトキシ、または2-エトキシである、特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 15【請求項15】Y n は、水素である、特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 16【請求項16】Y n は、4-ハロゲンである、特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 17【請求項17】Y n は、2-メトキシ、2-エトキシ、または2-プロポキシである、特許請求の範囲第2項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 18【請求項18】アルファ-〔2-(4-クロロフェニル)エチル〕-アルファ-フェニル-1H-1,2,4-トリアゾール-1-プロパンニトリルである、特許請求の範囲第7項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 19【請求項19】アルファ-(4-ブロモフェニル)-アルファ-〔2-(4-クロロフェニル)エチル〕-1H-1,2,4-トリアゾール-1-プロパンニトリルである、特許請求の範囲第7項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 20【請求項20】アルファ-(2-クロロフェニル)-アルファ-〔2-(4-クロロフェニル)エチル〕-1H-1,2,4-トリアゾール-1-プロパンニトリルである、特許請求の範囲第8項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 21【請求項21】アルファ-〔2-(4-クロロフェニル)エチル〕-アルファ-(2-メトキシフェニル)-1H-1,2,4-トリアゾール-1-プロパンニトリルである、特許請求の範囲第9項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 22【請求項22】アルファ-〔2-(3-ブロモフェニル)エチル〕-アルファ-フェニル-1H-1,2,4-トリアゾール-1-プロパンニトリルである、特許請求の範囲第13項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 23【請求項23】アルファ-フェニル-アルファ-〔2-(4-トリフルオロメチルフェニル)エチル〕-1H-1,2,4-トリアゾール-1-プロパンニトリルである、特許請求の範囲第14項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 24【請求項24】Zは、-CH=CH-であり、 Ar(X n )は、任意的に置換されたフェニルまたはナフチルであり、 Ar(Y n )は、任意的に置換されたフェニルであり、XおよびYは、独立的に、同じかまたは異っており、かつハロゲン、トリフルオロメチル、ヒドロキシ、メトキシ、エトキシ、プロポキシ、メチル、エチル、フェニル、およびナフチルから成る群から選ばれ、 mおよびnは、独立的に、0、1、または2である、特許請求の範囲第1項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 25【請求項25】Zは、(E)異性体である、特許請求の範囲第24項記載の化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩。
- 26【請求項26】農業上許容される担体、および活性成分として、 式 〔式中、 Zは、エチレン、エテニレン、エチニレン、イソプロピレン、ハロゲン化されたエチレン、ハロゲン化されたエテニレン、またはハロゲン化されたイソプロピレンであり、 Ar(X m )は、置換または非置換のC 6 -C 10 芳香族環構造であり、Ar(Y n )は、置換または非置換のC 6 -C 10 芳香族環構造、または、4個の炭素原子および1個の酸素もしくは硫黄原子を有する5員環、または、1個の窒素原子および5個の炭素原子を有する6員環、または、2個の窒素原子および4個の炭素原子を有する6員環であり、 XおよびYは、独立的に、同じかまたは異っており、かつハロゲン、任意的に3個までのハロゲンで置換された(C 1 -C 6 )アルキル、任意的に3個までのハロゲンで置換された(C 1 -C 6 )アルケニル、ヒドロキシ、(C 1 -C 6 )アルコキシ、(C 2 -C 6 )アルケノキシ、任意的に2個までのハロゲンで置換されたフェニル、シアノ、アミノ、6個までの炭素原子を有するモノアルキルアミノ、各アルキル基に6個までの炭素原子を有するジアルキルアミノ、-C(O)H、(C 1 -C 6 )アルキルスルホニル、アリールスルホニル、および-C(O)NR 1 R 2 (式中、R 1 およびR 2 は、独立に水素または(C 1 -C 6 )アルキル)から成る群から選ばれ、 Rは、水素、または、任意的に3個までのハロゲン、トリフルオロメチル、もしくは(C 1 -C 6 )アルキルで置換されたフェニルであり、 mおよびnは、独立的に、0~3である〕 を有する化合物、およびそれらの農業上許容される光学的対掌体、酸付加塩、および金属塩錯塩、の殺菌有効量を含有する、植物生病原生物である菌類の防除用殺菌性組成物。
- 27【請求項27】アリール基、シアノ基およびメチルトリアゾール基に結合している第4級炭素原子を有する、式 〔式中、 Zは、エチレン、エテニレン、エチニレン、イソプロピレン、ハロゲン化されたエチレン、ハロゲン化されたエテニレン、またはハロゲン化されたイソプロピレンであり、 Ar(X m )は、置換または非置換のC 6 -C 10 芳香族環構造であり、Ar(Y n )は、置換または非置換のC 6 -C 10 芳香族環構造、または、4個の炭素原子および1個の酸素もしくは硫黄原子を有する5員環、または、1個の窒素原子および5個の炭素原子を有する6員環、または、2個の窒素原子および4個の炭素原子を有する6員環であり、 XおよびYは、独立的に、同じかまたは異っており、かつハロゲン、任意的に3個までのハロゲンで置換された(C 1 -C 6 )アルキル、任意的に3個までのハロゲンで置換された(C 1 -C 6 )アルケニル、ヒドロキシ、(C 1 -C 6 )アルコキシ、(C 2 -C 6 )アルケノキシ、任意的に2個までのハロゲンで置換されたフェニル、シアノ、アミノ、6個までの炭素原子を有するモノアルキルアミノ、各アルキル基に6個までの炭素原子を有するジアルキルアミノ、-C(O)H、(C 1 -C 6 )アルキルスルホニル、アリールスルホニル、および-C(O)NR 1 R 2 (式中、R 1 およびR 2 は、独立に、水素または(C 1 -C 6 )アルキル)から成る群から選ばれ、 Rは、水素であり、 mおよびnは、独立的に0~3である〕 を有する化合物を製造する方法であって、 アリール基、シアノ基、および水素原子に結合している第3級炭素原子を有する化合物と、水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、または水素化カリウムのような塩基を、ジメチルスルホキシドまたはジメチルホルムアミドのような溶剤中で、好ましくは1時間~6時間撹拌することによって、第3級炭素含有化合物を塩基と反応させて第3級アニオンを生成し、それから、ハロメチルトリアゾールまたはその酸塩を加え、そして好ましくは1時間~24時間撹拌することを含んでおり、反応は好ましくは0°C~100°Cで行われ、第3級炭素含有化合物は であり、そしてハロメチルトリアゾールまたはその酸塩は である〔式中、Z、Ar(X m )、Ar(Y n )、X、Y、mおよびnは前記定義通りであり、そしてX 1 はハロゲンである〕、 前記式(I)の化合物の製造方法。
Independent claims27
2 paragraphs, as filed
Description: TECHNICAL FIELD [Detailed description of the invention]
Background of the invention The present invention relates to alpha-aryl-alpha-phenyl-ethyl-1H-1,2,4-triazole-1-propanenitrile, and the use of these compounds for the control of fungi that are phytopathogenic organisms. The phenethyl and aryl moieties may be substituted or unsubstituted. U.S. Pat. No. 4,363,165 of Miller et al. Describes the use of 1- and 4-arylcyanoalkyl-1,2,4-triazole, and their compounds against fungi that are phytopathogenic organisms. Has been done. However, neither the Fenetyltriazole nor the benzyltriazole of the present invention was prepared by Miller et al. Therefore, they were not aware of a particular class of compounds of the invention, nor were they aware that this class had a particularly high degree of bactericidal activity. The fuene tiltriazole of the present invention provides wheat powdery mildew, wheat stem rust, and wheat leaf rust. Not only is it effective against rust, but also barley helminthosporium, rice blast, and peanut early leaf spots. Is significantly superior to benzyltriazole and phenyltriazole. European Patent Application No. 52,424 (published May 26, 1982) comprehensively describes the compounds of the invention. However, none of the compounds of the present invention have been made. In fact, none of the examples of this European patent application No. 52,424 has a cyano group linked to a quaternary carbon and has either a hydroxy, methoxy, butoxy, or allyloxy group. I'm just there. The three Fenetyl triazole compounds described and produced in this European patent application No. 52,424 are 4,4-dimethyl-3-hydroxy-3- (1,2,4-triazole-1-yl). Methyl-1- (halogen substituted phenyl) -pentane. The published German Patent Application No. 3,216,301 describes the bactericidal activity of alkoxytriazole-propionitrile. European Patent Application No. 63,099 describes the use of chloromethyltriazole to make 1H-1,2,4-triazole-1-yl-methylphosphonium salt. Published UK Patent Application No. 2,119,374 describes a method for producing an alpha- (alkoxy, alkenoxy, alkoxy, or phenylalkoxy) -alpha-aryl-triazolylmethylacetonitrile compound. Description of the invention According to the present invention Equation (I)<img file="JPH0655729B2_D0001.tif" />[In the formula, Z is ethylene (-CH)<sub>2</sub>CH<sub>2</sub>-), Ethenylene (-CH = CH-), Echinylene (-CC-), or Isopropylene (-), Isopropylene (-)<img file="JPH0655729B2_D0002.tif" />Or halogenated ethylene, ethenylene or isopropylene; Ar (X)<sub>m</sub>) Is a substituted or unsubstituted C<sub>6</sub>-C<sub>10</sub>Aromatic ring structure; Ar (Y)<sub>n</sub>) Is a substituted or unsubstituted aryl, or a 5-membered ring having 4 carbon atoms and 1 oxygen or sulfur atom, or a 6-membered ring having 1 nitrogen atom and 5 carbon atoms. A ring, or a 6-membered ring with 2 nitrogen atoms and 4 carbon atoms; X and Y are independently the same or different, and halogen, optionally up to 3 halogens. Alkyl substituted with, optionally up to 3 halogen-substituted alkenyl, hydroxy, alkoxy, alkenoxy, optionally up to 2 halogen-substituted phenyl, cyano, optionally substituted amino, -C (O) H, -C (O) NR<sub>1</sub>R<sub>2</sub>(In the formula, R<sub>1</sub>And R<sub>2</sub>Is independently hydrogen or alkyl), alkylsulfinyl, and alkylsulfonyl; R is hydrogen, or optionally substituted phenyl; and m and n are independently. , 0 ~ 3] A novel class of triazole propanenitrile is provided, which is an alpha-aryl-alpha-phenylethyl-1H-1,2,4-triazole-1-propanenitrile with. In addition, new classes of these triazole propanenitriles include agriculturally acceptable optical antipode, acid addition salts, and metal complex salts of formula (I). The meaning of the term "aryl" is substituted and unsubstituted C<sub>6</sub>-C<sub>10</sub>Aromatic ring structure, 5-membered aromatic ring with 4 carbon atoms and 1 nitrogen atom, oxygen atom, or sulfur atom, or 6 with 1 or 2 nitrogen atoms and 5 or 4 carbon atoms A member aromatic ring is included. The meaning of the term "alkyl" is a carbon atom, preferably C.<sub>1</sub>-C<sub>8</sub>Both branched or straight chain alkyl groups are included. Typical alkyl groups included in this term include methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, neo-pentyl, iso-pentyl. , Hexyl, peptyl, iso-octyl and the like are included. As used herein, the meaning of the term "alkoxy" includes alkenoxy, a group consisting of an alkyl group attached to an oxygen atom. The preferred group is (C<sub>1</sub>-C<sub>6</sub>) Alkoxy is included. Typical alkoxy groups included in this term include methoxy, ethoxy, propoxy, n-butoxy, iso-butoxy, pentoxy, hexoxy, and allyloxy. The term "alkylsulfonyl" is -SO<sub>m</sub>R (in the formula, m is 0, 1 or 2 and R is an alkyl or aryl group). Preferably R is (C<sub>1</sub>-C<sub>6</sub>). The acids used to make the acid addition salts of the present invention include, for example, hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, hydroiodide, hydrofluoric acid, perchloric acid, p-toluenesulfonic acid. , Methansulfonic acid, acetic acid, citric acid, tartaric acid, malic acid, maleic acid, oxalic acid, fumaric acid, and phthalic acid. In another aspect of the invention, Equation (II)<img file="JPH0655729B2_D0003.tif" />[In the formula, Z, Ar (Y<sub>n</sub>), X, Y, n and m are the same as the definition of formula (I) above, and M is a cation selected from the IIA, IB, IIB, VIB, VIIB, and VIII groups in the periodic table. Yes, X<sup>1</sup>Is cation M and anion X<sup>1</sup>An anion chosen so that the sum of its valence charges is equal to 0] It is a metal salt complex salt having. Typical cations contained in the present invention include magnesium, manganese, copper, nickel, zinc, iron, cobalt, calcium, tin, cadmium, mercury, chromium, lead, barium and the like. Typical anions included in the present invention include chlorides, bromides, iodides, fluorides, sulfates, bicarbonates, perchlorates, nitrates, nitrites, phosphates, carbonates, bicarbonates, etc. Acetate, citrate, oxalate, tartrate, malate, maleate, fumarate, p-toluenesulfonate, (C<sub>1</sub>-C<sub>4</sub>) There are alkylene bisdithiocarbamate and the like. In a preferred embodiment of the invention, compounds of formulas (I) and (II) (where Z is ethyl, Ar is phenyl, and X and Y are hydrogen, halogen or trifluoromethyl). There are agriculturally acceptable optical antipode, salts, and complex salts. In a more preferred embodiment of the invention, (in the formula, Yn is hydrogen, 2-alkoxy, 4-halo, or 3-trifluoromethyl, and X is hydrogen, 4-halo, or 4-trifluoromethyl. There are compounds (which are methyl). In another preferred embodiment, a compound of (in the formula, Y is 2-halo and X is 4-halo, or Y is 4-halo and X is 2-halo). is there. Still other preferred compounds are compounds (in the formula, X is 3-halo and Y is hydrogen). The following compounds are included in the produced typical compounds contained in the present invention. 1. Alpha- (4-chlorophenyl) -alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 2. Alpha-phenyl-alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 3. Alpha- (2-Methoxyphenyl) -Alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 4. Alpha- (4-fluorophenyl) -alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 5. Alpha- (2,4-dichlorophenyl) -Alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 6. Alpha- (4-chlorophenyl) -alpha- [2- (4-chlorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 7. Alpha- (4-chlorophenyl) -alpha- [2- (4-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 8. Alpha- (4-chlorophenyl) -alpha- [2- (4-methylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 9. Alpha- (4-chlorophenyl) -alpha- [2- (4-methoxyphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 10. Alpha-[2- (4-chlorophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 11. Alpha-[2- (4-fluorophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 12. Alpha- (2-phenylethyl) -alpha- (4-phenylphenyl) -1H-1,2,4-triazole-1-propanenitrile 13. Alpha-phenyl-alpha- [2- (2-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 14. Alpha-phenyl-alpha- [2- (3-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 15. Alpha-[2- (2,4-dichlorophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 16. Alpha-[2- (4-Bromophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 17. Alpha-[2- (2-chlorophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 18. Alpha-[2- (3-chlorophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 19. Alpha-phenyl-alpha- [2- (4-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 20. Alpha- (4-chlorophenyl) -alpha- [2- (3-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 21. Alpha- (4-fluorophenyl) -alpha- [2- (3-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 22. Alpha-[2- (4-Bromophenyl) ethyl] -Alpha- (4-chlorophenyl) -1H-1,2,4-triazole-1-propanenitrile 23. Alpha- (4-chlorophenyl) -alpha- [2- (4-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 24. Alpha- (4-fluorophenyl) -alpha- [2- (4-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 25. Alpha- [2- (4-bromophenyl) ethyl] -Alpha- (2-fluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 26. Alpha- [2- (4-chlorophenyl) ethyl] -Alpha- (4-fluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 27. Alpha-[2- (3-bromophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 28. Alpha- (4-fluorophenyl) -alpha- [2- (4-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 29. Alpha- (2-methoxyphenyl) -alpha- [2- (4-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 30. Alpha- [2- (3-chlorophenyl) ethyl] -Alpha- (4-fluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 31. Alpha- (4-chlorophenyl) -alpha- [2- (3-chlorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 32. Alpha- (4-Bromophenyl) -Alpha- (2-phenylethyl) -1H-1,2,4-Triazole-1-Propionitrile 33. Alpha- (4-bromophenyl) -alpha- [2- (4-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 34. Alpha- (3-chlorophenyl) -Alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 35. Alpha- (3-chlorophenyl) -alpha- [2- (4-chlorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 36. Alpha- (3-chlorophenyl) -alpha- [2- (4-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 37. Alpha-4-bromophenyl-alpha- [2- (4-chlorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 38. Alpha- [2- (3-bromophenyl) ethyl] -Alpha- (4-fluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 39. Alpha- [2- (3-bromophenyl) ethyl] -Alpha- (4-chlorophenyl) -1H-1,2,4-triazole-1-propanenitrile 40. Alpha- (2-chlorophenyl) -alpha- [2- (4-chlorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 41. Alpha- [2- (4-chlorophenyl) ethyl] -Alpha- (2-fluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 42. Alpha- (4-chlorophenyl) -alpha- [2- (2-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 43. Alpha- (4-fluorophenyl) -alpha- [2- (2-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 44. Alpha- (2-chlorophenyl) -alpha- [2- (4-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 45. Alpha- (2-fluorophenyl) -alpha- [2- (4-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 46. Alpha- [2- (4-chlorophenyl) ethyl] -Alpha- (3-trifluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 47. Alpha- [2- (4-chlorophenyl) ethyl] -Alpha- (3-fluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 48. Alpha- (2-bromophenyl) Alpha- [2- (4-chlorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 49. Alpha- [2- (4-chlorophenyl) ethyl] -Alpha- (2-methoxyphenyl) -1H-1,2,4-triazole-1-propanenitrile 50. Alpha- (2-phenylethyl) -alpha- (3-trifluoromethylphenyl) -1H-1,2,4-triazole-1-propanenitrile 51. Alpha- (3-trifluoromethylphenyl) -alpha- [2- (3-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 52. Alpha- (3-fluorophenyl) -alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 53. Alpha- (3-chlorophenyl) -alpha- [2- (3-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 54. Alpha- (2-Bromophenyl) -Alpha- (2-phenylethyl) -1H-1,2,4-Triazole-1-Propionitrile 55. Alpha- (2-Bromophenyl) -Alpha- [2- (3-Trifluoromethylphenyl) Ethyl] -1H-1,2,4-Triazole-1-Propionitrile 56. Alpha- (3-fluorophenyl) -alpha- [2- (3-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 57. Alpha- (2-chlorophenyl) -alpha- [2- (3-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 58. Alpha-[2- (2-methoxyphenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 59. Alpha-[2- (3-methoxyphenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 60. Alpha-[2- (3,4-dimethoxyphenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 61. Alpha- [2- (4-chlorophenyl) ethyl] -Alpha- (4-methoxyphenyl) -1H-1,2,4-triazole-1-propanenitrile 62. Alpha- (4-Methoxyphenyl) -Alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 63. Alpha- (2-Chloro-6-fluorophenyl) -Alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 64. Alpha- (2-chloro-6-fluorophenyl) -alpha- [2- (4-chlorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 65. Alpha- [2- (4-chlorophenyl) ethyl] -Alpha- (2,6-dichlorophenyl) -1H-1,2,4-triazole-1-propanenitrile 66. Alpha-[2- (3-bromophenyl) ethyl] -Alpha- (3-chlorophenyl) -1H-1,2,4-triazole-1-propanenitrile 67. Alpha-[2- (4-Bromophenyl) ethyl] -Alpha (3-chlorophenyl) -1H-1,2,4-triazole-1-propanenitrile 68. Alpha- [2- (3-bromophenyl) ethyl] -Alpha- (3-fluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 69. Alpha- [2- (4-bromophenyl) ethyl] -Alpha- (3-fluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 70. Alpha-phenyl-alpha- (2-phenyl) propyl-1H-1,2,4-triazole-1-propanenitrile 71. Alpha- (3-fluorophenyl) -alpha- [2- (4-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 72. Alpha- [2- (4-fluorophenyl) ethyl] -Alpha- (3-trifluoromethylphenyl) -1H-1,2,4-triazole-1-propanenitrile 73. Alpha-[2- (1-naphthyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 74. Alpha-[2- (4-bromophenyl) ethyl] -Alpha- (2-ethoxyphenyl) -1H-1,2,4-triazole-1-propanenitrile 75. Alpha- [2- (4-bromophenyl) ethyl] -Alpha- (3-trifluoromethylphenyl) -1H-1,2,4-triazole-1-propanenitrile 76. Alpha- (2-ethoxyphenyl) -Alpha- [2- (3-trifluoromethylphenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 77. Alpha- (2-ethoxyphenyl) -Alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile 78. Alpha- [2- (4-chlorophenyl) ethyl] -Alpha- (2-ethoxyphenyl) -1H-1,2,4-triazole-1-propanenitrile 79. Alpha- (2-ethoxyphenyl) -Alpha- [2- (4-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 80. Alpha-[2- (3,4-dichlorophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 81. Alpha- (3-chlorophenyl) -alpha- [2- (3-chlorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 82. Alpha- (3-chlorophenyl) -alpha- [2- (3-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 83. Alpha-[2- (3-fluorophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 84. Alpha- [2- (3-chlorophenyl) ethyl] -Alpha- (2-methoxyphenyl) -1H-1,2,4-triazole-1-propanenitrile 85. Alpha- (4-Bromophenyl) -Alpha- [2- (3-Chlorophenyl) Ethyl] -1H-1,2,4-Triazole-1-Propionitrile 86. Alpha- (4-chlorophenyl) -alpha- [2- (3-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 87. Alpha- (3-Bromophenyl) -Alpha- (2-phenylethyl) -1H-1,2,4-Triazole-1-Propionitrile 88. Alpha-[2- (3-bromophenyl) ethyl] -Alpha- (2-ethoxyphenyl) -1H-1,2,4-triazole-1-propanenitrile 89. Alpha- (3-fluorophenyl) -alpha- [2- (3-fluorophenyl) ethyl] -1H-1,2,4-triazole-1-propanenitrile 90. Alpha- (4-Bromophenyl) -Alpha- [2- (3-Bromophenyl) Ethyl] -1H-1,2,4-Triazole-1-Propionitrile 91. Alpha- [2- (3-chlorophenyl) ethyl] -Alpha- (3-fluorophenyl) -1H-1,2,4-triazole-1-propanenitrile 92. Alpha-[2- (3,5-dichlorophenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 93. Alpha-[2- (4-Methoxyphenyl) ethyl] -Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile 94. Alpha-[2- (4-chlorophenyl) ethyl] -Alpha-phenyl-beta-1H-1,2,4-triazole-1-propanenitrile 95. Alpha-[2- (4-chlorophenyl) ethyl] -Alpha- (2-thienyl) -1H-1,2,4-triazole-1-propanenitrile 96. Alpha- [2- (4-chlorophenyl) ethyl] -Alpha- (2-pyridyl) -1H-1,2,4-triazole-1-propanenitrile 97. Alpha-phenyl-alpha-() (2-phenylethenyl) -1H-1,2,4-triazole-1-propanenitrile 98. Alpha-phenyl-alpha-() [2- (4-chlorophenyl) ethenyl] -1H-1,2,4-triazole-1-propanenitrile The chemical structure of compound 1-96 is shown in Table 1 below. ..<img file="JPH0655729B2_D0004.tif" /><img file="JPH0655729B2_D0005.tif" /><img file="JPH0655729B2_D0006.tif" /><img file="JPH0655729B2_D0007.tif" /><img file="JPH0655729B2_D0008.tif" />Table 2 shows other examples included in the present invention.<img file="JPH0655729B2_D0009.tif" /><img file="JPH0655729B2_D0010.tif" />Comparative compounds manufactured and tested include the following compounds: C2a. Alpha, Alpha-Diphenyl-1H-1,2,4-Triazole-1-Propionitrile C2b. Alpha-benzyl-Alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile C6. Alpha- (4-chlorobenzyl) -Alpha- (4-chlorophenyl) -1H-1,2,4-triazole-1-propanenitrile C10. Alpha- (4-chlorobenzyl) -alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile The chemical structure of the comparative compound is shown below.<img file="JPH0655729B2_D0011.tif" /><img file="JPH0655729B2_D0012.tif" /><img file="JPH0655729B2_D0013.tif" /><img file="JPH0655729B2_D0014.tif" />The triazole of the present invention can be produced by a conventional synthetic route. For example, the triazole of the present invention uses a salt of alhua- (bromomethyl) -alpha- (2-phenylethyl) -phenylacetonitrile (VIII) and triazole in a generally about 1-3 equivalents, preferably an alkali metal salt. It can be produced by a nucleophilic substitution reaction. The reaction is carried out in the absence of a solvent, or preferably in a suitable solvent such as dimethyl sulfoxide (DMSO), N, N-dimethylformamide (DMF), toluene or xylene, from about 0 ° C to about 150 ° C. It can be carried out at a temperature of about 25 ° C to about 100 ° C, preferably. The compound (VIII) is obtained by hydrogenating alpha-2-phenylethyl-phenyl acetonitrile (IX) with methylene bromide (generally about 1.1-about 2 equivalents) under basic conditions such as sodium hydroxide or potassium, for example. Sodium or potassium, potassium methoxyde, and potassium-t-butoxide (generally about 1. Under conditions of 1-about 2 equivalents), preferably using a solvent, such as DMSO containing sodium hydroxide or DMF containing hydrides and oxides, about 0 ° C-about 150 ° Manufactured by bromomethylation at a temperature of C, preferably about 25 ° C-about 100 ° C. Compound (IX) is a strong base, eg, 50%, with the appropriate substituted benzyl cyanide (X), using about 1-2 equivalents of 2-phenylethylmethanesulfonate (mesylate) or toluenesulfonate (tosilate). It can be prepared by phase transition alkylation in the presence of (w / w) sodium hydroxide or other metal alkoxide, and in the presence of a catalyst such as tetrabutylammonium bromide. Compound (IX) also contains a suitable substituted benzyl cyanide in the presence of a strong base, such as a metal hydride, such as sodium hydride or potassium hydride, using about 1-2 equivalents of 2-phenylethyl halide. Underneath, it can be produced by alkylation with DMF or DMF / toluene as the solvent. Benzyl cyanide and alkyl halide can be easily produced by using a technique known from the literature and the like. An illustration of these composites is shown below.<img file="JPH0655729B2_D0015.tif" />Fenetyltriazole (I) can be produced in one step by the reaction of phenylethyl-phenylacetonitrile (IX) with halomethyltriazole (XI) in a solvent such as DMF. Two equivalents of strong bases such as sodium hydride or potassium hydride are used. The synthetic route is shown below.<img file="JPH0655729B2_D0016.tif" />This reaction is not limited to the production of the triazole of the present invention. This reaction is also used to produce compounds with quaternary carbons attached to aryl, cyano, and triazole groups, as described in US Pat. No. 4,366,165 and UK Patent Application No. 2,119,374. be able to. The method described in the prior art requires an additional step to produce an aryl-cyano- (halomethyl, alkylsulfonyloxymethyl, or arylsulfonyloxymethyl) compound that reacts with a triazole or alkali metal triazole derivative. .. This additional step is omitted by the method of the present invention. The acid addition salt of triazole of the present invention can be produced by a standard technique known in the art. For example, the triazole of formula (I) is dissolved in a suitable solvent such as diethyl ether, tetrahydrofuran, ethanol, methanol, etc., or a mixture thereof, and the inorganic acid or organic acid which is not or dissolved in a suitable solvent. It is treated in equal or excess amounts and then the mixture is cooled or evaporated to produce a salt that can be used as is or can be recrystallized from a suitable solvent or mixture of suitable solvents. The metal complex salt of triazole of the present invention is obtained by adding a chemical amount of a metal salt dissolved in a suitable solvent or a mixture of solvents to a solution of triazole of the formula (I) similarly dissolved in a suitable solvent or a mixture of solvents. It can be made by dropping while stirring. The reaction mixture is stirred for a short time and the solvent is removed under reduced pressure to give each metal complex of formula (II). Also, the metal complex salt is produced by mixing a stoichiometric amount or an excess amount of the metal salt with triazole in a desired amount of a solvent containing a suitable auxiliary agent immediately before spraying on the plant. Can be done. Auxiliary agents contained in the production immediately before spraying include detergents, emulsifiers, wetting agents, spreading agents, dispersants, pressure-sensitive adhesives, adhesives and the like used for agricultural applications. Solvents that can act on these operations include any polar solvent such as water, methanol, ethanol, isopropanol, or ethylene glycol, and any aprotic dipolar solvent such as dimethyl sulfoxide, acetonitrile. , Dimethylformamide, nitromethane, or acetone. The metal salt cations used in these operations are calcium, magnesium, manganese, copper, nickel, zinc, iron, cobalt, tin, cadmium, mercury, chromium, lead, barium and the like. Suitable anions such as chlorides, bromides, iodides, sulfates, bicarbonates, phosphates, nitrates, perchlorates, carbonates, bicarbonates, hydroxide hydroxide hydroxides, acetates, oxalates , Apple salts, citrates, etc. can be used as opposite ions in metal salts. The compound of the present invention has an asymmetric carbon atom and exists as a racemic mixture. The d and optical antipode in these racemic mixtures are separated by standard techniques such as fractional crystallization using d-tartaric acid, -tartaric acid, -quinic acid, etc., then basicized and d or It can be obtained by extracting the free base of the optical racemate. The optical antipode, acid addition salt, and metal complex salt of the present invention are useful as agricultural fungicides and can be applied to various places such as seeds, soil, or leaves. For such purposes, the compounds of the invention can be used in technically pure form as manufactured, or as a solution, or as a formulation. The compounds of the present invention are usually placed in a carrier and formulated to be suitable for spraying as a fungicide. For example, these chemical agents of the present invention can be formulated as wet powders, emulsifying concentrates, dust, granular formulations, aerosols, or fluid emulsifying concentrates. In such formulations, the compounds of the invention may be augmented with a liquid or solid carrier and optionally supplemented with a suitable surfactant. Usually, especially in the case of formulations for spraying on the leaves, according to agricultural practices, auxiliaries such as wetting agents, spreading agents, dispersants, adhesives, adhesives and the like may be included. desirable. Auxiliary agents commonly used in such techniques can be found in "Detergents and Emulsifiers, Annual" published by John W. McCutchen, Inc. In general, the compounds of the present invention can be dissolved in certain solvents, such as acetone, methanol, ethanol, dimethylformamide, or dimethylsulfoxide, and the solution can be augmented with water. The concentration of the solution can be varied from about 1% to about 90%, with a preferred range of about 5% to about 50%. The emulsifying concentrate can be produced by dissolving the compound of the present invention in a suitable solvent or solvent mixture together with an emulsifier that disperses the bactericide, which is the compound, in water. The concentration of the active ingredient in the emulsifying concentrate is usually about 10% to about 90%, and in the fluid emulsifying concentrate, this concentration is about 75%. Wetting powders suitable for dusting can also be obtained by mixing the compounds of the present invention with dispersants and finely ground solids such as clay, inorganic silicates, carbonates, silica, and such mixtures. It can be produced by optionally adding a wetting agent and an adhesive to the silica. The concentration of active ingredient in such formulations usually ranges from about 20% to about 98%, preferably from about 40% to about 75%. A typical wetting powder is 50 parts of alpha- [2- (4-chlorophenyl) ethyl] -alpha- (2-methoxyphenyl) -1H-1,2,4-triazole-1-propanenitrile. Hi-Sil<sup></sup>It can be made by mixing 45 parts of synthetic precipitated hydrated silicon dioxide sold under the name of , 1 part of sodium lauryl sulfate, and 5 parts of sodium lignosulfonate. Another process is to use kaolin-type (Barden) clay instead of Hi-Sil in the wet powder. In other manufacturing methods, 25% of Hi-Sil is Zeolex.<sup></sup>7 Replace with sodium silicoaluminate sold under the name of . The dust can be produced by mixing the thiazole of the present invention, its optical antipode, salt, and complex salt with an organic or inorganic finely milled inert solid. Substances useful for this purpose include vegetable fines, silica, silicates, carbonates, and clays. One convenient way to make dust is to dilute the wetting powder with a finely ground carrier. Usually, a dust concentrate containing about 20% to about 80% of the active ingredient is made, which is then diluted to a working concentration of about 1% to about 10%. The optical antipode, salts, and complex salts of the present invention are commonly used methods such as high gallon hydraulic spraying, low gallon spraying, air spraying, air spraying, and spraying. , Can be applied as a spray of bactericide. The dilution rate and ratio for application can be easily determined by the equipment used, the desired method, the timing of application, the number of applications, the plants to be treated, the disease to be controlled, and the like. However, in general, the bactericidal compounds of the present invention, when applied to leaves or soil, are applied in an amount of about 0.01 to about 20 lbs of active ingredient per acre. For use as a seed protectant, the amount of the compound coated on the seed is typically about 0.05 to about 4 ounces of active ingredient per 100 lbs of seeds, preferably 0.1 to about 1 ounce per 100 lbs of seeds. Is. For use as a soil fungicide, the compound typically contains about 0.05 to about 20 lbs, preferably about 0.02 to about 10 lbs, more preferably about 0.1 to about 3 lbs of active ingredient per acre of soil. Formulate inside or apply to its surface. For use as a leaf fungicide, the compound is typically about 0.01 to about 10 lbs, preferably about 0.02 to about 5 lbs, more preferably about 0.03 to about 1 lb of active ingredient per acre. Apply to growing plants in proportion. The fungicides that can be used in combination with the fungicides of the present invention include: (a) Dithiocarbamate and its derivatives: For example, ferbam dimethyldithiocarbamate [ferbam], zinc dimethyldithiocarbamate [ziram], manganese ethylenebisdithiocarbamate [maneb], and coordination formation of zinc ions with the compound. Compounds [mancozeb], zinc ethylenebisdithiocarbamate [zineb], zinc propylene bisdithiocarbamate [propineb], sodium methyldithiocarbamate [metham], tetramethylthiuramdi Sulfide [thiram], a compound salt of zineb and polyethylene thiuram disulfide, 3,5-dimethyl-1,3,5-2H-tetrahydrothiazine-2-thione [dazomet], and A mixture of these, and a mixture with copper salt, (b) Nitrophenol derivative: For example, dinitro- (1-methylheptyl) phenyl-crotonate [dinocap], 2-sec-butyl-4,6-dinitrophenyl, -3,3-dimethyl-acrylate [binapacryl], and 2- sec-Butyl-4,6-dinitrophenylisopropylcarbonate, (c) Heterocyclic compound: For example, Systhane (registered trademark of myclobutanil Rohm and Haas Co.), N-trichloromethylthiotetrahydrophthalimide [captan], N-trichloromethylthiophthalimide [folpet], 2- Heptadecil-2-imidazole acetate [glyodine], 2-octylisothiazolone-3-one, 2,4-dichloro-6- (o-chloro-anilino) -s-triazine, diethyl Phthalimide phosphorothioate, 4-butyl-1,2,4-triazole, 5-amino-1- [bis- (dimethylamino) phosphinyl] -3-phenyl-1,2,4-triazole, 5-ethoxy- 3-Trichloromethyl-1,2,4-thiadiazole, 2,3-dicyano-1,4-dithianonone [dithianon], 2-thio-1,3-dithio- [4,5-b ] Kinoxalin-2-thione [thioquinox], methyl 1- (butylcarbamoyl) -2-benzimidazole carbamate [benomyl], 2,4'-(thiabendazole) benzimidazole [thiabendazole] ), 4- (2-Chlorophenylhydrazono) -3-methyl-5-isoxazolone, pyridine-2-thiol-1-oxide, 8-hydroxyquinoline Sulfate and its metal salts, 2,3-dihydro-5-carboxyanilide-6-methyl-1,4-oxathione-4,4-dioxide, 2,3-dihydro-5-carboxyanilide-6-methyl-1 , 4-Oxatiin, α- (phenyl) -α- (2,4-dichlorophenyl) -5-pyrimidinyl-methanol [triarimol], cis-N-[(1,1,2,2-tetra) -Chloroethyl) thio] -4-cyclohexane-1,2-dicarboxyimide, 3- [2- (3,5-dimethyl-2-oxycyclohexyl-2-hydroxy] -glutaliimide [cycloheximide], Dehydroacetic acid, N- (-1,1,2,2-tetrachloroethylthio) -3a,4,7,7a-tetrahydrophthalimide [captafol], 5-butyl-2-ethylamino-4-hydroxy-6 -Methylpyrimidine [ethirimol], 4-cyclodecyl-2,6-dimethyl-morpholine acetate [dodemorph], and 6-methyl-2-oxo-1,3-dithiolo [4,5- b]-Kinoxalin [quinomethionate], (d) Other halogenated fungicides: For example, tetrachloro-p-benzoquinone [chloranil], 2,3-dichloro-1,4-naphthoquinone [dichlone], -1,4-dichloro-2,5-dimethoxybenzene [chloroneb]. )], 3,5,6-trichloro-o-anisic acid [tricamba], 2,4,5,6-tetrachloroisophthalonitrile (TCPN)], 2,6-dichloro-4-nitroaniline [Dichloran], 2-chloro-1-nitropropane, polychloronitrobenzene, such as pentachloronitrobenzene (PCNB), and tetrafluorodichloroacetone, (e) Sterilizing antibiotics: For example, griseofulvin, kasugamycin, streptomycin, (f) Copper-based fungicide: For example, cuprous oxide, basic cupric chloride, basic copper carbonate, copper naphthenate, and Bordeaux mixture, (g) Other disinfectants for rice: For example, tricilazole, iso-prothiolane, probenazole, propiconazole, edifenphos, oo-diisopropyl-benzyl-thiophosphate, iprodion, procymidone, bincrozoline, benomyl, thioffanate methyl, mepronil, tencyclon, and validamycin and, (h) Other disinfectants: For example, diphenyl, dodecylguanidine acetate [dodine], phenylmercuric acetate, N-ethylmerkyury-1,2,3,6-tetrahydro-3,6-endomethano-3,4,5,6,7 , 7-Hexachlorophthalimide, phenylmarkyuric monoethanolammonium lactate, p-dimethylaminobenzene diazonium sulfonate, methyl isothiocyanate, 1-thiacyano-2,4-dinitrobenzene, 1-phenylthiosemicarbazide, nitkel-containing compound, Calcium cyanamide, lime sulfur, sulfur, -1,2, -bis (3-methoxycarbonyl-2-thioureide) benzene [thiophanate-methyl). The optical antipode, acid addition salt, and metal complex salt of the present invention can be advantageously used in a variety of ways. Due to their wide range of fungicidal activity, these compounds can be used as fungicides in lawns, fruit trees, plant crops, cereal crops, golf courses, grain storage and the like. Other applications of the present invention will of course be understood by those skilled in the art of agriculture and horticulture. Example Overall, the substituted benzyl cyanide was synthesized into alpha-phenyl-alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile by three steps. In the first step, benzyl cyanide was alkylated using one of three methods. In the second step, the alkylated phenylacetonitrile was bromomethylated using one of four methods. In the third step, the alkylated triazole propanenitrile was synthesized from the alkylated phenylacetonitrile bromide by nucleophilic substitution with potassium triazole. In this third step, potassium triazole was pre-synthesized and added to the bromide. Alternatively, add equal parts of potassium hydroxide, triazole, and DMSO to the equivalent of toluene, heat at 100-120 ° C for 2 hours, distill off the toluene, remove the co-boiling water, and remove this newly produced potassium. The bromide was added to triazole. In this third step, potassium triazole was made in-situ by the reaction of potassium carbonate and triazole in methyl ethyl ketone (MEK) or DMSO solvent. A two-step procedure was used to make alpha-phenyl-alpha- (2-phenylethyl) -1H-1,2,4-triazole-1-propanenitrile. The first step is the same as the step for the three-step operation. However, the product of step 1 was coupled with chloromethyltriazole HC via a base in DMF. At least 2 equivalents of base were used. Anions were formed at room temperature, then a solid HC salt was added. The second equivalent liberated the salt into the free base, chloromethyltriazole, which reacted with the anion. Hydroxides, alkoxides, or hydrides can be used as the base. NaOH or KOH can be used, but on an experimental scale NaH is preferred. If the formation of anions is more difficult, KH is preferred for less acid intermediates. A similar operation with chloromethyltriazole HC is to liberate the salt into a free base prior to addition. This is CH<sub>2</sub>C<sub>2</sub>It can be carried out with NaOH in the medium, then the addition is carried out with DMF using NaOH as the base or DMSO with NaOH as the base after removing the solvent. Halogenated phenetiltriazole is a corresponding phenetyltriazole with n-chlorosuccinimide (NCS) or n-bromosuccinimide (NBS) in the presence of a catalyst or initiator, such as benzoyl peroxide. It can be produced by reacting with. Fenetilt triazole is dissolved in an inert solvent such as carbon tetrachloride and 1 or 2 equivalents of halogenating agent is used. Triazole halides can be converted to ethenyl compounds by base excision repair with metal hydroxides or metal alkoxides. Typical bases include sodium hydroxide, sodium methoxide, and potassium tert-butoxide. These steps and the method for producing Compound 1-96 are summarized in Tables 3 and 4.<img file="JPH0655729B2_D0017.tif" /><img file="JPH0655729B2_D0018.tif" /><img file="JPH0655729B2_D0019.tif" /><img file="JPH0655729B2_D0020.tif" /><img file="JPH0655729B2_D0021.tif" />Table 5 shows the melting points and elemental analysis values of compounds 1-96, respectively. The amounts of chlorine, fluorine, and oxygen have not been measured in all of the examples. The NMR of compounds 70, 95 and 96 is shown following Tables 4 and 5.<img file="JPH0655729B2_D0022.tif" /><img file="JPH0655729B2_D0023.tif" /><img file="JPH0655729B2_D0024.tif" />NMR was measured for compounds 70, 95, and 96. The results are shown below. Compound 70: NMR (90MHz): [Mixture of diastereoisomers]: 1.2-1.6 (two doublets, 3H), 2.4-2.8 (m, 3H), 4.6-4.9 (two overlaps ABq, 2H), 7.0-7.8 (m, 10H), 7.90 (s, 1H) and 8.0 (s, 1H). Compound 95: NMR (90MHz): 2.0-2.4 (m, 4H), 4.8 (ABq, 2H), 6.9-7.4 (m, 7H), 7.8 (s, 1H) and 7.9 (s, 1H). Compound 96: NMR (90MHz): 2.2-2.9 (m, 4H), 4.7-5.0 (ABq, 2H), 7.0-7.4 (ABq, 4H), 7.4-7.8 (m, 3H) and 8.6-8.7 (br d) , 1H). Next, a production example of a typical compound of the present invention will be shown. Compound 14: Method for producing alpha-phenyl-alpha- [2- (3-trifluoromethylphenyl) ethyl] -1,2,4-triazole-1-propanenitrile: Process 1 Alpha-[2- (3-trifluoromethylphenyl) ethyl] phenylacetonitrile production In a 500 m 4-neck round bottom flask, 11.0 g (0.275 mol, 1.1 eq) of 60% NaH (washed twice with hexane) was placed in 50 m of dry DMF. The reaction mixture was cooled to 0 ° C., and a solution prepared by dissolving 29.4 g (0.25 mol, 1.0 equivalent) of benzyl cyanide in 50 m of toluene was added dropwise. The reaction was warmed to room temperature, then cooled to -20 ° C, and 52 g (0.25 mol, 1.0 eq) of 3-trifluoromethylphenethyl chloride was added dropwise in 50 m of DMF. The reaction was stirred at -20 ° C for 3 hours and then subjected to gas-liquid chromatography to show 60% monoalkylate and 40% dialkylate. The reaction was cooled with water and extracted with ether. Then, it was dried and concentrated, and the obtained crude product was chromatographed by high performance liquid chromatography [(95: 5) hexane: ethyl acetate] to obtain 19.2 g (yield 26.3%) of 97% pure product. It was. This mixture was used directly in the next step. NMR (60MHz): 2.0-2.4 (m, 2H), 2.7-3.0 (m, 2H), 3.6-3.9 (t, 1H) and 7.2-7.4 (d, 9H). Process 2 Production of 1-Bromo-2-cyano-2-phenyl-4- (3-trifluoromethylphenyl) butane 19.0 g (0.064 mol, 1.0 eq) of alpha- [2- (3-trifluoromethylphenyl) ethyl] phenylacetonitrile and CH in a 500 m 4-neck flask<sub>2</sub>Br<sub>2</sub>17 g (0.097 mol, 1.5 eq) of DMSO was dissolved in 50 m of DMSO. The reaction was stirred at room temperature and 10.3 g (0.128 mol, 2.0 eq) of 50% NaOH was added dropwise. The reaction was warmed to 50 ° C and stirred for 2 hours. The reaction was cooled with water, extracted with ether, dried and concentrated to give 25 g (yield 96.9%) of the product. This product was used directly for the coupling of triazole. NMR (60MHz): 2.2-2.8 (m, 4H), 3.7 (s, 2H) and 7.2-7.6 (m, 9H). Process 3 Alhua-phenyl-alpha- [2- (3-trifluoromethylphenyl) ethyl] -1,2,4-triazole-1-Propionitrile A 250 m 4-neck round-bottom flask was filled with a solution of 4.05 g (0.062 mol, 1.25 eq) of 87% KOH and 4.8 g (0.068 mol, 2.2 eq) of triazole in 25 m of DMSO. The reaction was warmed to 90 ° C until homogeneous, 25 m of toluene was added and azeotroped for 4 hours. Toluene was distilled off at 165 ° C and the reaction was cooled to 100 ° C, 12.5 g (0.031 mol) of 1-bromo-2-cyano-2-phenyl-4- (3-trifluoromethylphenyl) butane. , 1.0 equivalent) was added. The reaction was heated at 125 ° C. for 1 hour, then cooled with water, extracted with ethyl acetate, dried and concentrated. Purification with high-pressure liquid chromatographie [(1:) hexane: ethyl acetate] gave 8.8 g (yield 76.7%) of a white solid. This melting point was 127-128 ° C. IR (nujol, cm<sup>-1</sup>): 2980 (s), 2240 (w), 1430 (s), 1380 (s), 1330 (s), 1280 (m) 1200 (m), 1160 (s), 1140 (s), 1130 (s) , 1120 (s), 1075 (m), 1025 (w), 800 (m), 710 (s) and 670 (s). NMR (60MHz): 2.4-2.9 (m, 4H), 4.6 (s, 2H), 7.3-7.5 (s, 4H), 7.7 (s, 1H) and 7.9 (s, 1H). Elemental analysis: C<sub>20</sub>H<sub>17</sub>N<sub>4</sub>F<sub>3</sub>Calculated values: C: 64.83, H: 4.63, N: 15.14, F: 15.39 Measured values: C: 65.13, H: 4.52, N: 15.09, F: 15.22 Compound 20: Method for producing alpha- (4-chlorophenyl) -alpha- [2- (3-trifluoromethylphenyl) ethyl] -1,2,4-triazole-1-propanenitrile: Process 1 Alpha-[2- (3-trifluoromethylphenyl) ethyl] -4-chlorophenylacetonitrile production A 500 m single-necked round-bottom flask was filled with 4.4 g (0.11 mol, 1.0 eq) of 60% NaH (washed 3 times with 25 m hexane) in 100 m of 2: 1 benzene / DMF. Then 15.1 g (0.10 mol, 1.0 eq) of 4-chlorobenzylcyanide was added and stirred at room temperature for 2 hours. With stirring at room temperature, 20.8 g (0.1 mol, 1.0 eq) of 3- (trifluoromethyl) phenethyl chloride was added dropwise over several hours. Then, stirring was continued overnight at room temperature. The product was cooled with water, extracted with ether, distilled and concentrated. 16.2 g (yield 50.1%) of the product was obtained. NMR (60MHz): 2.0-3.0 (m, 4H), 3.5-3.8 (t, 1H), 7.3 (s, 4H) and 7.5 (s, 4H). Process 2 Production of 1-Bromo-2-cyano-2- (4-chlorophenyl) -4- (3-trifluoromethylphenyl) butane 16.2 g (0.05 mol), 1.0 eq of alpha- [2- (3-trifluoromethylphenyl) ethyl] -4-chlorophenylacetonitrile in a 300 m single-necked round-bottom flask.<sub>2</sub>Br<sub>2</sub>17.4 g (0.10 mol, 2.0 eq) of the above was dissolved in 50 m of DMSO and a solution was added. The reaction was stirred at room temperature and 10 g of 50% NaOH was added dropwise and exotherm was observed. The reaction was stirred for 45 minutes. It was found that the reaction was completed by gas-liquid chromatographie. The product was cooled with water and extracted with ether. It was dried and the solvent was removed. 20.8 g (yield 100%) of yellow oil was obtained. NMR (60MHz): 2.0-3.2 (m, 4H), 3.8 (s, 2H) and 7.5-7.6 (d, 10H). Process 3 Alpha- (4-Chlorophenyl) -Alpha- [2- (3-Trifluoromethylphenyl) Ethyl] -1,2,4-Triazole-1-Propionitrile 10.7 g (0.10 mol, 4.0 eq) of potassium triazole, 75 m of DMSO, and 1-bromo-2-cyano-2- (4-chlorophenyl) -4- (3-tri) in a 500 m single-necked round-bottom flask. Fluoromethylphenyl) butane (10.4 g, 0.025 mol, 1.0 eq) was added. The reaction was heated at 80 ° C. overnight, then cooled by adding 1 of water and extracted 3 times with 200 m of ether. The ether extracts were combined, washed with water and brine, then dried and distilled to give the crude product. It was made into a slurry with ether: hexane (1: 1). The resulting solid was washed with hexane to give 5.0 g (47% yield) of a pale yellow solid. This melting point was 118-121 ° C. NMR (60MHz): 2.4-3.2 (m, 4H), 5.0-5.2 (br s, 2H), 7.6-7.9 (br s, 8H), 8.1 (s, 1H) and 8.4 (s, 1H). Calculated values: C: 59.32, H: 3.99, N: 13.85, C: 8.76, F: 14.09 Measured values: C: 59.46, H: 4.20, N: 13.25, C: 9.48, F: 13.36 Compound 44: Preparation of alpha- (2-chlorophenyl) -alpha- [2- (4-fluorophenyl) ethyl] -1,2,4-triazole-1-propanenitrile: Process 1 Production of 2- (4-fluorophenyl) ethyl methanesulfonate. Mesylation of 2- (4-fluorophenyl) ethanol. 42.04 g (0.3 mol, 1.0 eq) of 2- (4-fluorophenyl) ethanol in a 500 m 3-necked round-bottom flask equipped with a condenser and an addition funnel and capable of stirring in the presence of nitrogen. A solution dissolved in 100 m of tetrahydrofuran (THF) was added. The reaction was cooled to 10 ° C and 60.7 g (0.60 mol, 2.0 eq) of triethylamine was added directly. A solution of 68.73 g (0.6 mol, 2.0 eq) of methanesulfonyl in 30 m of THF was added dropwise to this while maintaining a temperature of 30 ° C. or lower. Further, 150 m of THF was added and the reaction was stirred for 6 hours. The reaction was cooled with 200 m of water and 300 m of ether was added. Wash this ether with 75 m of 10% HC and saturate LVDS<sub>3</sub>It was washed twice with 50 m of liquid and twice with 50 m of water, dried and concentrated. 58.0 g (yield 88.7%) of brown liquid was obtained. NMR (90MHz): 2.9 (s, 3H), 2.9-3.2 (m, 2H), 4.2-4.4 (t, 2H) and 6.9-7.4 (m, 4H). Process 2 Alpha-[2- (4-fluorophenyl) ethyl] -2-chlorophenylacetonitrile production. In a 300 m 4-neck round bottom flask, 4.26 g (0.105 mol, 1.05 eq) of 60% NaH (washed 3 times with 25 m of hexane) was placed in 60 m of DMF. Then, a solution prepared by dissolving 15.16 g (0.10 mol, 1.0 eq) of 2-chlorophenylacetonitrile in 40 m of DMF was added, and the mixture was stirred at 10 ° C. for 1 hour. Then, a solution prepared by dissolving 2- (4-fluorophenyl) ethylmethane sulfonate (22.2 g, 0.102 mol) in 50 m of DMF was added dropwise. The reaction was complete after 2 hours. It was then cooled at 10 m with 10% HC. To this was added 60 m of water, extracted with 200 m of ether and washed twice with 50 m of 10% HC. It was then dried and concentrated. 27.15 g of crude product was obtained. This was subjected to vacuum distillation to obtain 17.46 g (yield 63.5%) of an oil having a boiling point of 180-188 ° C at 1 mmHg. NMR (90MHz): 2.2-2.4 (t, 2H), 2.8-3.0 (m, 2H), 3.8-3.9 (t, 2H) and 6.9-7.5 (m, 8H). Process 3 Production of Alpha- (2-Chlorophenyl) -Alpha- [2- (4-Fluorofenyl) Ethyl] -1,2,4-Triazole-1-Propionitrile A 200 m 3-necked round-bottom flask was filled with a solution of 2.3 g (0.055 mol, 2.75 eq) of 60% NaH (washed twice with 25 m of hexane) in 40 m of DMF. The reaction was cooled to 10 ° C, and 5.46 g (0.02 mol, 1.0 eq) of alpha- [2- (4-fluorophenyl) ethyl] -2-chlorophenylacetonitrile was dissolved in 40 m of DMF. It was added over 10 minutes while dropping. After 20 minutes, 3.12 g (0.0204 mol, 1.02 eq) of chloromethyltriazole HC was added directly in two portions. One hour later, the gas-liquid chromatographie revealed that the reaction was complete. 20 m of water was added to the reaction product and cooled. CH the product<sub>2</sub>C<sub>2</sub>It was extracted using 200 m of water and washed twice with 50 m of water. After drying and concentration, an orange oil was obtained. This was crystallized from ethyl ether. The product was filtered to give 2.5 g (35% yield) of a light yellowish brown solid. The melting point was 110-112 ° C. IR (nujol, cm<sup>-1</sup>): 1505 (m), 1440 (s), 1370 (m), 1270 (m), 1220 (m), 1130 (m) and 750 (m). NMR (90MHz): 2.2-3.0 (m, 4H), 3.8-4.2 (ABq, 2H), 6.9-7.4 (m, 7H), 7.8 (s, 1H) and 7.9 (s, 1H). Elemental analysis: C<sub>19</sub>H<sub>16</sub>N<sub>4</sub>FC Calculated values: C: 64.30, H: 4.55, N: 15.80, F: 5.36, C: 10.00 Measured values: C: 63.82, H: 4.56, N: 15.84, F: 5.30, C: 9.87 Compound 64: Alhua-(2-Chloro-6-fluorophenyl) -Alpha- [2- (4-chlorophenyl) ethyl] -1,2,4-triazole-1-Propionitrile Process 1 Alhua-[2- (4-chlorophenyl) ethyl] -2-chloro-6-fluorophenyl acetonitrile production A 200 m 3-necked round-bottom flask was filled with 7.5 g (0.187 mol, 1.5 eq) of 60% NaH (washed 3 times with 25 m of hexane) in 60 m of 2: 1 toluene: DMF. .. To this, 21.2 g (0.125 mol, 1.0 eq) of 2-chloro-6-fluorophenylacetonitrile was added dropwise over 0.5 hours in a solution of 2: 1 in toluene: DMF. The reaction was stirred at 10 ° C for 20 minutes and then at room temperature for 1 hour. Then, 32.1 g (0.137 mol, 1.1 eq) of 2- (4-chlorophenyl) ethylmethane sulfonate was added over 1 hour while dropping a solution of 2: 1 toluene: DMF in 60 m. Approximately 70 m of 2: 1 toluene: DMF was added under constant stirring and the reaction was stirred for an additional 3.5 hours. After that, it was investigated by gas-liquid chromatographie and it was found that the reaction was completed. Then 50 m of water was added, 10 m of 10% HC and 300 m of ether were added. The ether was washed with 100 m of water and extracted twice with 50 m of ether. Then it was washed with water. The ethers were combined, dried and concentrated to give 40.0 g of crude product. This was subjected to vacuum distillation. 26.6 g (69.8%) of the product was obtained. It had a boiling point of 175-185 ° C at 1 mmHg. NMR (90MHz): 2.2-2.9 (m, 4H), 4.2-4.4 (t, 1H) and 7.0-7.4 (m, 7H). Process 2 Production of 1-bromo-2-cyano-2- (2-chloro-6-fluorophenyl) -4- (4-chlorophenyl) butane A 200 m 3-necked round-bottom flask was filled with 2.4 g (0.048 mol, 1.2 eq) of 60% NaH (washed twice with 25 m of hexane) in 40 m of DMF. At room temperature, a solution of 12.28 g (0.04 mol, 1.0 equivalent) of alpha- [2- (4-chlorophenyl) ethyl] -2-chloro-6-fluorophenylacetonitrile dissolved in 30 m of DMF was added dropwise for 0.5 hours. I added it over. Then CH<sub>2</sub>Br<sub>2</sub>10.43 g (0.60 mol, 1.5 eq) of DMF was added dropwise to 20 m of DMF, and the reaction was stirred at room temperature for 5 hours. After that, it was found that the reaction was completed by gas-liquid chromatography. After 1 hour, 20 m of water was added to the reaction to cool the reaction, 200 m of ether was added and it was separated. After washing with water, it was dried and concentrated to obtain 14.84 g of a product (yield 92.9%). It was used directly for the coupling of triazole. NMR (90MHz): 2.4-2.8 (m, 4H), 3.8-4.2 (ABq, 2H) and 6.9-7.3 (m, 7H). Process 3 Alhua-(2-Chloro-6-fluorophenyl) -Alpha- [2- (4-chlorophenyl) ethyl] -1,2,4-Triazole-1-Propionitrile 14.84 g (0.038 mol, 1.0 eq) of 1-bromo-2-cyano-2- (2-chloro-6-fluorophenyl) -4- (4-chlorophenyl) butane in a 200 m single-necked round-bottom flask. Was dissolved in 50 m of DMSO. To this reaction was added a solution of 4.89 g (0.0457 mol) of K-triazole dissolved in 30 m of DMSO, and the flask was heated to 120 ° C. After 1.5 hours at 120 ° C, gas-liquid chromatography revealed that the reaction was complete. After cooling to room temperature, 50 m of water was added and 250 m of ethyl acetate was added. After separation, the organic phase was washed twice with 100 m of water, concentrated and ground with ether. The solid was filtered, the filtrate was concentrated and ground with ether. The obtained solid was further filtered to obtain 8.06 g (yield 54.6%) of the product at the joint. This melting point was 98-99 ° C. IR (nujol, cm<sup>-1</sup>): 3020 (m), 1600 (s), 1570 (m), 1500 (s), 1450 (s), 1275 (s), 1240 (m), 1205 (m), 1135 (m), 910 (m) ), 890 (s) and 790 (s). NMR (90MHz): 2.4-3.2 (m, 4H), 4.8-5.2 (ABq, 2H), 6.9-7.4 (m, 7H), 7.9 (s, 1H) and 8.2 (s, 1H). Elemental analysis: C<sub>19</sub>H<sub>5</sub>N<sub>4</sub>FC<sub>2</sub>Calculated values: C: 58.60, H: 3.89, N: 14.40, F: 4.88, C: 18.22 Measured values: C: 58.43, H: 3.91, N: 14.43, F: 4.78, C: 17.89 Compound 74: Preparation of alpha- [2- (4-bromophenyl) ethyl] -alpha- (2-ethoxyphenyl) -1,2,4-triazole-propanenitrile Process 1 Alhua-[2- (4-bromophenyl) ethyl] -2-ethoxyphenylacetonitrile production In a 4-necked round-bottom flask of 1, 5.6 g (0.14 mol, 1.4 eq) of 60% NaH (washed 3 times with 25 m of hexane) was dissolved in 100 m of 2: 1 toluene: DMF. .. Then, 16.1 g (0.10 mol, 1.0 eq) of 2-ethoxybenzyl cyanide was dissolved in 200 m of 2: 1 toluene: DMF, and the mixture was stirred at room temperature for 2 hours. After this, a solution of 5.7 g (0.05 mol, 0.5 eq) of KH (washed with 25 m of hexane) in 50 m of 2: 1 toluene: DMF was added. After an additional hour, 31 g (0.11 mol, 1.1 eq) of 4-bromophenylmethanesulfonate was added over 10 minutes with a solution of 2: 1 toluene: DMF dissolved in 100 m. The reaction was stirred at room temperature overnight. The reaction product was found to be 81% monoalkylated by gas-liquid chromatography. The reaction was cooled with 10% HC, 400 m of ether was added and washed 4 times with 150 m of water. The solvent was dried over magnesium sulfate and then concentrated to give 37 g of crude orange oil. The solid was then crystallized, filtered and washed with cold toluene. White solid 14.8 g (yield 43.7%). NMR (90MHz): 1.3-1.5 (t, 3H), 2.0-2.3 (m, 2H), 2.2-2.9 (m, 2H), 3.9-4.2 (m, 3H) and 6.8-7.5 (m, 8H). Process 2 Production of 1-Bromo-2-cyano-2- (2-ethoxyphenyl) -4- (4-Bromophenyl) butane A 500 m 3-necked round-bottom flask was filled with 3.5 g (0.087 mol, 2.0 eq) of 100% KH (washed twice with 25 m of hexane) in 25 m of DMF. At room temperature, 14.8 g (0.044 mol, 1.0 eq) of alpha- [2- (4-bromophenyl) ethyl] -2-ethoxyphenylacetonitrile was added dropwise in 60 m of DMF. 1 hour later, CH<sub>2</sub>Br<sub>2</sub>(0.066 mol, 1.5 eq) was added while dropping a solution prepared in 40 m of DMF. This reaction generated heat and reached 45 ° C. After stirring at room temperature for 3 hours, gas-liquid chromatography revealed that the reaction was 85% complete. The reaction was stirred at room temperature overnight, then 0.8 g (0.8 g (0.022 mol, 0.5 eq)) of 100% KH was added in 20 m of DMF and CH was added.<sub>2</sub>Br<sub>2</sub>A solution prepared by dissolving 1.2 g of the above in 5 m of DMF was added. After 1 hour, the reaction was complete. 75 m of 10% HC was added to the reaction to cool the reaction, then 300 m of ether was added. After washing 4 times with 100 m of water, the product was dried and the solvent was removed by evaporation. 18.3 g of orange-yellow oil (yield 96.8%) was obtained. NMR (60MHz): 1.3-1.6 (t, 3H), 2.2-2.8 (m, 4H), 3.7-4.2 (m, 4H) and 6.8-7.6 (m, 8H). Process 3 Production of Alpha- [2- (4-Bromophenyl) Ethyl] -Alpha- (2-ethoxyphenyl) -1,2,4-triazole-1-propanenitrile 18.3 g (0.43 mol, 1.0 eq) of 1-bromo-2-cyano-2- (2-ethoxyphenyl) -4- (4-bromophenyl) butane in a 300 m 3-necked round-bottom flask 100 m of DMSO The solution dissolved in was added. To this reaction, 5.4 g (0.050 mol) of K-triazole was added at room temperature, and the reaction was stirred at 100 ° C. for 20 hours. It was found that the reaction was completed by gas-liquid chromatographie. The reaction was cooled by adding 10% HC, then ether was added. During the extraction, the product crystallized. The volume of solvent was reduced and the product was filtered. 11.3 g (63% yield) of a light yellowish brown solid was isolated. Its melting point was 130-132 ° C. IR (nujol, cm<sup>-1</sup>): 1590 (w), 1265 (m), 1245 (m), 1135 (m), 1030 (m) and 750 (m). NMR (60MHz): 1.4-1.6 (t, 3H), 1.9-2.9 (m, 4H), 4.0-4.4 (q, 2H), 4.9 (s, 2H), 6.8-7.4 (m, 8H) and 7.8 ( s, 2H). Elemental analysis: C<sub>21</sub>H<sub>21</sub>N<sub>4</sub>BrO Calculated values: C: 59.28, H: 4.98, N: 13.18, O: 3.76, Br: 18.80 Measured values: C: 59.42, H: 5.06, N: 13.12, O: 3.99, Br: 18.60 Compound 83: Alhua-[2- (3-fluorophenyl) ethyl] -Alpha-phenyl-1,2,4-Triazole-1-Propionitrile Process 1 Production of 1- (hydroxymethyl) -1,2,4-triazole A 500 m 3-neck round-bottom flask equipped with a cooler and a mechanical stirrer was filled with 69.1 g (1 mol) of triazole, 30.1 g of paraformaldehyde, and 1 m of triethylamine in THF. The reaction was stirred for 18 hours while refluxing under a nitrogen atmosphere. The mixture was then concentrated on an evaporator (rotovap). The obtained white solid was concentrated and washed with ether to obtain 96.8 g (yield 97.6%) of the product. It had a melting point of 67-70 ° C. The product was further purified by dissolving in hot acetone, cooling to room temperature, filtering the solid and washing with ether. Process 2 In a 4-neck / flask equipped with a cooler, an addition funnel, and a mechanical stirrer, 45 g (0.464 mol) of 1- (hydroxymethyl) -1,2,4-triazole was dissolved in 500 m of THF. It was added and heated to 40 ° C with vigorous stirring. The SOC is then maintained at a temperature of 45 ° C.<sub>2</sub>(61 m, 0.84 mol) was added. During the addition, the resulting precipitate and mixture were stirred for an additional 2 hours. The product was filtered, washed 3 times with ethyl acetate and dried in vacuo at room temperature. The product was 67.3 g (yield 94.2%). This melting point was 118-130 ° C. Process 3 Production of 2- (3-fluorophenyl) ethanol. Reduction of 3-fluorophenylacetic acid via diborane reduction. A solution of 75 g (0.48 mol) of 3-fluorophenylacetic acid dissolved in 100 m of THF was placed in a 2-four-necked flask equipped with a cooler and an addition funnel, and the mixture was stirred under a nitrogen atmosphere. Then, 500 m (0.50 mol) of 1 M diborane THF complex salt was added dropwise. This addition generated a gas. The reaction was cooled and maintained at a temperature below 10 ° C. After completion of the addition, the reactants were stirred at room temperature until the reaction was confirmed by thin layer chromatography. The reaction was cooled by adding ice water to the reaction, the product was extracted with ether, then washed with 5% NaOH, 5% HC and water and dried over magnesium sulphate. After concentration, 77.3 g of brown oil was obtained. NMR (90MHz): 2.6 (2,1H), 2.7-2.9 (t, 2H), 3.7-3.9 (t, 2H) and 6.9-7.4 (m, 4H). Process 4 Manufacture of 2- (3-fluorophenyl) ethyl chloride. Chlorination of 2- (3-fluorophenyl) ethanol. In a 500 m 4-neck flask equipped with a cooler and an addition funnel, 14.0 g (0.1 mol, 1.0 equivalent) of 2- (3-fluorophenyl) ethanol was dissolved in 60 m of toluene and placed in a nitrogen atmosphere. Stirred below. The SOC is then kept below 15 ° C by external cooling.<sub>2</sub>22 m (35.9, 0.30 mol, 3.0 eq) was added while dropping. A solution prepared by dissolving pyridine (8.7 g, 1.1 eq) in 10 m of toluene was added dropwise. After stirring the reaction at room temperature overnight, it was found that the reaction was completed by thin layer chromatography. The mixture was concentrated, water was added, extracted with ether, washed with water and the product was isolated. After drying and concentration, 10.2 g (yield 64.5%) of orange oil was obtained. NMR (60MHz): 2.9-3.2 (m, 2H), 3.5-3.8 (m, 2H) and 6.8-7.4 (m, 4H). Process 5 Alpha-[2- (3-fluorophenyl) ethyl] phenylacetonitrile production In a 3-necked round-bottom flask of 1, 5.6 g (0.140 mol, 1.4 eq) of 60% NaH (washed 3 times with 25 m of hexane) was dissolved in 100 m of 2: 1 toluene: DMF. .. Then, a solution prepared by dissolving 11.7 g (0.10 mol, 1.0 eq) of benzyl cyanide in 150 m of 2: 1 toluene: DMF was added, and the mixture was stirred for 2 hours. Then, a solution prepared by dissolving 2- (3-fluorophenyl) ethyl chloride (20 g, 0.126 mol) in 100 m of 2: 1 toluene: DMF was added. This reaction was completed after 3 hours. It was cooled using 10 m of 10% NC. Water was added, extracted with 300 m of ether and washed 4 times with 100 m of water. It was then dried and concentrated. 22.5 g of crude product was obtained. It was distilled under reduced pressure. 11.2 g of product (yield 46.9%) was obtained. It had a boiling point of 160-163 ° C at 1 mmHg. NMR (90MHz): 2.0-2.3 (m, 2H), 2.6-2.8 (m, 2H), 3.6-3.8 (t, 1H) and 6.8-7.5 (m, 9H). Process 6 Alhua-[2- (3-fluorophenyl) ethyl] -Alpha-phenyl-1,2,4-triazole-Propionitrile production A 500 m 4-neck round-bottom flask was filled with 0.3 g (0.075 mol, 3.0 eq) of 60% NaH (washed twice with 25 m of hexane) in 50 m of DMF. To this reaction product, 6.0 g (0.025 mol, 1.0 equivalent) of alpha- [2- (3-fluorophenyl) ethyl] -phenylacetonitrile was added while dropping a solution prepared in 200 m of DMF. After 1 hour, 6.0 g (0.038 mol, 1.5 eq) of chloromethyltriazole HC was added directly in two portions. After 1 hour, gas-liquid chromatographies revealed that the reactants were incomplete. Further, a solution prepared by dissolving 1.5 g (1.5 eq) of 60% NaH (washed with 25 m of hexane) in 25 m of DMF was added. The reaction was completed in 1 hour, then ether containing methanol was added and cooled. Then 25 m of 10% HC was added and 300 m of ether was added. It was washed with water (150 m) 4 times, dried and concentrated to obtain 5 g of yellow oil. The product was crystallized from ether to give 2.3 g (yield 29%) of the product. This melting point was obtained at 100-101 ° C. IR (nujol, cm<sup>-1</sup>): 1580 (w), 1265 (m) and 1140 (m). NMR (90MHz): 2.2-2.8 (m, 4H), 4.6 (d, 2H), 6.8-7.6 (m, 9H) and 7.8-7.9 (d, 2H). Elemental analysis: C<sub>19</sub>H<sub>17</sub>N<sub>4</sub>F Calculated values: C: 71.21, H: 5.35, N: 5.94, F: 17.50 Measured values: C: 71.20, H: 5.36, N: 5.93, F: 17.44 Compound 88: Preparation of alpha- [2- (3-bromophenyl) ethyl] -alpha- (2-ethoxyphenyl) -1,2,4-triazole-1-propanenitrile: Process 1 Production of 2- (3-bromophenyl) ethanol. Reduction of 3-bromophenylacetic acid via diborane reduction. A solution of 75 g (0.34 mol) of 3-bromophenylacetic acid dissolved in 100 m of THF was placed in a 2-four-necked flask equipped with a cooler and an addition funnel, and the mixture was stirred under a nitrogen atmosphere. Then 350 m (0.35 mol) of 1 M diborane THF complex salt was added dropwise. The addition generated a gas. The reaction was cooled and the temperature was maintained below 10 ° C. After completion of the addition, the reactants were stirred at room temperature until the reaction was confirmed to be complete by thin layer chromatography. The reaction was cooled with ice water and the product was extracted with ether, then washed with 5% NaOH, 5% HC, water and dried over magnesium sulphate. After concentration, 77.4 g of product was obtained. This was directly based. NMR (90MHz): 2.7-2.9 (m, 3H), 3.7-3.9 (t, 2H) and 7.1-7.4 (m, 4H). Process 2 Manufacture of 2- (3-bromophenyl) ethyl chloride. Chlorination of 2- (3-bromophenyl) ethanol. In a 500 m 3-necked round-bottom flask equipped with a cooler and an addition funnel, 20.0 g (0.1 mol, 1.0 equivalent) of 2- (3-bromophenyl) ethanol was dissolved in 60 m of toluene, and a nitrogen atmosphere was added. Stirred below. SOC while maintaining the temperature below 15 ° C by external cooling<sub>2</sub>22 m (35.9 g, 0.30 mol, 3.0 eq) was added while dropping. A solution prepared by dissolving pyridine (8.7 g, 1.1 eq) in 10 m of toluene was added dropwise. After stirring the reaction at room temperature overnight, it was found that the reaction was completed by thin layer chromatography. The mixture was concentrated, water was added, extracted with ether, washed with water and then the product was isolated. After drying and concentrating, 14.2 g (yield 64.2%) of orange oil was obtained. NMR (60MHz): 2.8-3.1 (m, 2H), 3.5-3.8 (m, 2H) and 7.0-7.3 (m, 4H). Process 3 Alhua-[2- (3-bromophenyl) ethyl] -2-ethoxyphenylacetonitrile production In a 4-necked round-bottom flask of 1, 3.5 g (0.083 mol, 1.4 eq) of 60% NaH (washed 3 times with 25 m of hexane) was dissolved in 100 m of 2: 1 toluene: DMF. .. Then, a solution prepared by dissolving 9.5 g (0.059 mol, 1.0 eq) of 2-ethoxybenzyl cyanide in 200 m of 2: 1 toluene: DMF was added, and the mixture was stirred for 2 hours. Then, a solution prepared by dissolving 2- (3-bromophenyl) ethyl chloride (13 g, 0.059 mol) in 100 m of 2: 1 toluene: DMF was added. The reaction was not complete even after 20 hours. A solution prepared by dissolving 2.0 g (0.05 mol) of 100% KH in 25 m of DMF was added. After 4 hours, the reaction was complete. It was then cooled with 10% HC, extracted with ether, washed with water, dried and concentrated to give 20 g of crude oil (97% purity). This product was distilled under reduced pressure to obtain 12.3 g of the product (yield 58.9%). It had a boiling point of 195-210 ° C at 1 mmHg. NMR (90MHz): 1.2-1.4 (t, 3H), 2.0-2.3 (t, 2H), 2.6-2.9 (t, 2H), 3.8-4.2 (m, 3H) and 6.7-7.4 (m, 8H). Process 4 Alpha-[2- (3-bromophenyl) ethyl] -Alpha- (2-ethoxyphenyl) -1,2,4-triazole-1-propanenitrile A 500 m 4-neck round-bottom flask was filled with a solution of 2.8 g (0.07 mol, 3.0 eq) of 100% KH (washed twice with 25 m of hexane) in 50 m of DMF. To this reaction product was added dropwise a solution prepared by dissolving 8.0 g (0.023 mol, 1.0 equivalent) of alpha- [2- (3-bromophenyl) ethyl] -2-ethoxyphenylacetonitrile in 100 m of DMF. After 1 hour, 5.7 g (0.037 mol, 1.6 eq) of chloromethyltriazole HC was added directly in two portions. One hour later, a gas-liquid chromatographie revealed that the reaction was incomplete. Further, 2.8 g (3.0 eq) of KH was added, and 1.8 g (0.5 eq) of chloromethyltriazole / HC was added. After stirring overnight at room temperature, the reaction was complete. A small amount of MeOH was dissolved in 100 m of ether and cooled, and 10 m of 10% HC was added. Then 200 m of ether was added, washed 4 times with 100 m of water, dried and concentrated to give 7 g of crude oil. The product was purified by fractional chromatography using 1: 1 ethyl acetate: hexane to give 2.3 g (24% yield) of viscous oil. NMR (60MHz): 1.4-1.7 (t, 3H), 2.1-3.0 (m, 4H), 4.0-4.3 (m, 2H), 5.0 (s, 2H), 6.9-7.4 (m, 8H) and 7.8 ( s, 2H). Elemental analysis: C<sub>21</sub>H<sub>21</sub>N<sub>4</sub>BrO Calculated values: C: 59.28, H: 4.98, N: 13.18, O: 3.76, Br: 18.80 Measured values: C: 58.40, H: 5.43, N: 11.56, O: 6.30, Br: 17.69 Compound 93: Preparation of alpha- [2- (4-methoxyphenyl) ethyl] -alpha-phenyl-1,2,4-triazole-1-propanenitrile: Process 1 Alhua-[2- (4-methoxyphenyl) ethyl] -phenylacetonitrile production 117 g (1.0 mol, 2.0 eq) of benzyl cyanide and 115 g of 2- (4-methoxyphenyl) ethylmethanesulfonate in a 2-four-necked round-bottom flask equipped with a thermometer, a dropping funnel and a mechanical stirrer. (0.5 mol, 1.0 eq) was charged with a solution of 400 m of DMSO and 200 m of toluene. The reaction was cooled to 10 ° C. and 50 g (0.63 mol, 1.2 eq) of 50% NaOH was added dropwise over 30 minutes. The reaction heats up to 35 ° C and is cooled to 10 ° C. The reaction was stirred at room temperature for 48 hours and gas-liquid chromatographies resolved 60% product and 40% benzyl cyanide. The reaction was cooled by adding to water 2, then extracted 3 times with ether (1) and washed twice with water (1) and brine (1). DDL<sub>4</sub>The oil was then concentrated to give 171 g of crude oil (67% product). The product was distilled under reduced pressure to give 104 g of yellow oil (82.5% yield based on mesylate). It had a boiling point of 165-170 ° C at 2 mmHg. NMR (60MHz): 1.9-2.4 (m, 2H), 2.5-2.7 (m, 2H), 3.7 (s, 4H), 6.8-7.2 (ABq, 4H) and 7.5 (s, 5H). Process 2 Production of 1-bromo-2-cyano-2-phenyl-4- (4-methoxyphenyl) butane. In a 4-necked round-bottom flask of 1, 100 g (0.04 mol, 1.0 eq) of alpha- [2- (4-methoxyphenyl) ethyl] -phenylacetonitrile and 139.1 g of dibromomethane were dissolved in 200 m of DMSO. I put the liquid. To this reaction, 79.6 g (0.99 mol, 2.5 eq) of 50% NaOH was added dropwise over 15 minutes. The reaction exothermized to 95 °, then cooled to 50 ° C and stirred at 50 ° C for 1 hour. When the gas-liquid chromatographie revealed that the reaction was complete, the reaction product was injected into water 2. Ether (extracted 3 times at 500 m, washed with water (1) and brine, dried with sulfate. After concentration, 130 g (94% yield) of product was obtained as amber oil. This product. The material was used directly for the coupling of triazole. NMR (60MHz): 2.4-2.8 (m, 4H), 3.7 (s, 2H), 3.8 (s, 3H), 6.8-7.3 (ABq, 4H) and 7.5-7.8 (br s, 5H). Process 3 Production of Alpha-[2- (4-Methoxyphenyl) Ethyl] -Alpha-phenyl-1,2,4-triazole-Propionitrile In a three-necked flask of 1, 57 g (0.74 mol, 2.0 eq) of triazole was dissolved in 300 m of DMSO and K.<sub>2</sub>CO<sub>3</sub>102 g (0.74 mol, 4.0 eq) was added. After stirring the reaction at 135 ° C for 1 hour, 127 g (0.37 mol, 1.0 eq) of 1-bromo-2-cyano-2-phenyl-4- (4-methoxyphenyl) butane was added to 200 m of DMSO. The dissolved solution was added. The temperature dropped to 115 ° C. It was heated at 135 ° C for 2 hours and then at 80 ° C for 18 hours. The reaction was poured into water (3), extracted 5 times with ethyl acetate (500 m), washed 2 times with water (500 m) and washed with 500 m of brine. After drying with sulfate, it was filtered and concentrated to obtain a yellow oil. It was made into a slurry with hexane. The resulting yellow solid was filtered and washed with 10% diethyl ether / 90% hexane. After drying, 95 g (yield 77.4 g) of the product was obtained. It had a melting point of 91-94 ° C. NMR (60MHz): 2.4-2.9 (m, 4H), 3.9 (s, 3H), 5.1 (s, 2H), 6.8-7.4 (ABq, 4H), 7.7-7.9 (br s, 5H), 8.2 (s , 1H) and 8.4 (s, 1H). Elemental analysis: C<sub>20</sub>H<sub>20</sub>N<sub>4</sub>O Calculated: C: 72.24, H: 6.06, N: 16.87, O: 4.82 Analytical values: C: 72.55, H: 6.39, N: 16.09, O: 5.21 The activity of the compounds of the invention against a number of diseases was tested. The test compound was dissolved in acetone, methanol, and water to generate a 300ppm-5ppm diluent series. Depending on the test, various diluent series, such as 300, 75, 19, 5, or 100, 25, 6, were used. Unless otherwise noted, the plants were sprayed using a mechanical sprayer on the same day as the day of infection (inoculation) or the day before the day of infection until the diluent was drained. Wheat stem rust [Wheat Stem Rust (WSR)], wheat leaf rust [Wheat Leaf Rust (WLR)], wheat powdery mildew [Wheat Powdery Mildew (WPM)] and rice leaf blight [ The method of conducting the test for Rice Blast (RB)] was as follows. Wheat stalk rust [Wheat Stem Rust (WSR)-Puccina graminis] Wheat seedling varieties, TYLER, were grown on redi-earth and used for screening approximately 7 days after planting. Seedlings were fertilized with LIQUID-M (trademark of Universal Chemical Co.) prior to use in the test to maintain vibrant plants throughout the test period. In conducting the test, one of the following three methods was used to prepare a suspension of rust bacterium urediospore. 1. Water / Devilbiss Atomizer: The WSR spore suspension was harvested 2-3 weeks after cultivated plants and the leaves were vigorously shaken in water + TWEEN 80 (Fisher Scientific Co-) surfactant. .. The spore suspension was filtered through cheesecloth to remove leaf debris and adjusted to 3-5 spores per large square on the hemocytometer. Plants were inoculated using a devilbis sprayer. 2. Oil / Devil Bis Atomizer: WSR and oil spore suspensions were removed from infected plants 2-3 weeks old using a vacuum pump or rust collector to remove new spores or rehydrate frozen spores (strongly frozen). (Rehydrated from spores), and these spores were made by adding them to SOLTROL (trademark of Phillips Chemical Co.) spray oil to a concentration of 5 mg spores / 1 m oil. A devilbis sprayer was used to inoculate from all four sides to create one pass on the plant. The plants were dried for about 20 minutes and then placed in a damp cabinet. 3. Oil / extra small atomizer: A spore suspension was prepared by the same procedure as in Method 2 above. However, it was adjusted to 4 mg spores / 1 m oil. It was then dispensed into gelatin capsules and inoculated using a vacuum pump. Uniformed so that there were 4 paths on both sides of the plant. The plants were dried for about 20 minutes and then placed in a damp cabinet. Moist cabinets were coated with 100% undissolved water and maintained at a constant temperature of 70 ° F. The inoculated plants were left in the dark for 12 hours, followed by fluorescence for 3-4 hours. The plants were then transferred to the greenhouse and evaluated after 13 days. Wheat Leaf Rust (WLR)-Puccinia recondita The same operation used for WSR was used for WLR. However, WLR did not require light conditions. Powdery mildew of wheat [Wheat Powdery Mildew (WPM)-Erysiphe graminis] Wheat seedling varieties Victory 283 (VICTORY 283) were grown on redi-earth. These seedlings were left for 6-7 days and fertilized with LIQUID-M fertilizer to promote good growth throughout the test period before use in the test. Cultured plants that produced spores were sprinkled on these seedlings to infect them, and powdery mildew spores were sown. Infected seedlings were placed in underground irrigated trays and in a controlled temperature room providing a 70 ° F environment for disease development. The development of WPM is greatly affected by volatile chemicals. Therefore, the pots were spread as much as possible and the trays were separated by plastic sheets depending on the dose. Disease development was assessed as a percentage of control 7-10 days after infection. Rice leaf blight [Rice Blast (RB)-Piricularia oryzae] Seedlings of rice variety M-201 grow in a greenhouse at 20-30 ° C for 14 days in a 2-inch pot containing unpasteurized soil and Turf-Builder (Scotts Company trademark) soil. I let you. The inoculation source is oatmeal agar [gerber (trademark of Gerber Products Co.)} 50 g of baby oatmeal, 20 g of bacto agar, 10 g of bacto dextrose, deionized water. It was made in-vitro on [100 m]. Plates were infected with a Piricularia orygae mycelial plug [mycelial plug (7-14 days old)]. The outer edge of the dark area was used for movement. The infected plate was maintained at room temperature under constant fluorescence. A dish containing powdery mildew of rice aged 10-14 days was placed in a solution containing 0.25 g of sodium oleate, 2 g of gelatin, and 1000 m of deionized water. The dish is rubbed with a rubber policeman to release conidia, filtered through two layers of cheesecloth and a spore suspension using a hemacytometer. Was adjusted to 25000-30000 spores / m. The spore suspension was sprayed onto rice plants opposite two rows using a manual sprayer. The source of infection was sufficiently applied so that it was evenly distributed from the soil pot on the opposite side of each pot (about 50 m / 50 pot) to the tip of the rice leaf. The manual sprayer was shaken well after application to each pot to keep the suspension well suspended. Infected plants were immediately placed in a cabinet with a humidity of 25 ° C for 66 hours and then transferred to a plastic tent greenhouse. The plants were underground irrigated but never left in the water for more than 2 hours. The plastic side of the tent was open during working hours but closed at the end of the day. After 76 hours under temperature conditions, bioassay plants were observed to determine the percentage of disease control (compared to infected controls). The compounds of the present invention were tested using different dose ratios depending on the test. The results of these tests for one dose ratio of each compound are shown in Table 6. When the compound was tested more than once at that dose ratio, the average value was shown.<img file="JPH0655729B2_D0025.tif" /><img file="JPH0655729B2_D0026.tif" /><img file="JPH0655729B2_D0027.tif" /><img file="JPH0655729B2_D0028.tif" /><img file="JPH0655729B2_D0029.tif" />The test was performed using different dose ratios of the compounds. Table 7 shows the test results of the good compounds used in the test in the proportions of 3 types. When the compounds were tested at the same dose more than once, the average value was shown.<img file="JPH0655729B2_D0030.tif" /><img file="JPH0655729B2_D0031.tif" /><img file="JPH0655729B2_D0032.tif" /><img file="JPH0655729B2_D0033.tif" />Compound 28 was tested at 20 ppm.<img file="JPH0655729B2_D0034.tif" /><img file="JPH0655729B2_D0035.tif" />The activities of some of the compounds of the present invention were described in Peanut Cercospora (PC), Barley Helminthosporium (BH), and Wheat Septoria Nodorum (SNW). ] Was tested. The reports of these studies are shown below. Peanut spot disease [Peanut Cercospora or Peanut Early Leaf spot (PC)-Cercospora Arachidicola] Cercospora arachidicola was cultured on peanut automill agar (POA) in Petry dishes for 14 days under fluorescent lighting approximately 20 cm above the culture. The Petry dish was inoculated with 0.5 m of a spore suspension made in sterile water containing a few drops of TWEEN 80. The spore suspension was then applied onto the surface of the POA plate using a sterile hot case take-shaped bent glass rod. Spores were removed from the plate by adding deionized water containing a small amount of Tween 80 to the POA plate. The surface of the agar was scraped with a rubber policeman or something like a similar thick needle. The spore suspension is filtered through a cheesecloth to remove mycelium and agar debris, then 2-4 x 10<sup>5</sup>The concentration was adjusted to / m. The leaves of the TAMNUT 74 peanut plant grown for 14 days were inoculated by spraying the inoculum until the inoculated membrane was observed on the plant. The inoculated plants were kept warm for 72 hours in a humid environment of 85-90 ° F. The plants were removed from a damp environment, dried and placed in a greenhouse. Treatment comparisons were made 10-14 days after inoculation. Barley spotted disease [Baley Helminthosporium or Barley Spot Blotch Test (BH)-Helminthosporium sativum] In 2 pots, 7 days old HENREY barley saplings were pruned 24 hours before applying the chemicals to facilitate uniform height and uniform inoculation of the plants. These plants were sprayed with test compounds via an installed tower (1.1 m of desired concentration for each spray). The spray was placed in the tower for 1 minute before removing the plants from the tower. After spraying, the plants were dried in a drying hood for at least 2 hours before inoculation. Helminthosporium used for inoculation The sativum culture was deep black spore-forming after about 3 weeks. 5 m of deionized water was added to each Petry dish with culture and scraped into water using a rubber policeman. After scraping, the water was filtered through a cheesecloth to remove mycelium and agar pieces. One drop of TWEEN 80 surfactant was added to each 100 m of spore suspension. Inoculation was performed using a manual sprayer. The inoculated plants were placed in a damp cabinet at approximately 75 ° F for 24 hours and then placed in a greenhouse. The plants were placed in the greenhouse for 6 days before evaluating the test results. Illness was assessed by "A MANUAL OF ASSESSMENT KEYS FOR PLANT DISEASES" (Key NO.1.6.1) by clive james. Diseases that stain wheat bracts [Wheat Glume Blotch (SNW)-Septoria nodorum] Inoculate from a dish of sporogenic mycelial fragments 3 weeks old Czapek-Dox V-8) Place on a dish or in vitro sporogenic mycelial fragments containing 20 m of sterile deionized water, shake well, and after 5 minutes, a well-mixed liquid spore mixture is new. I made a thin film on the plate by putting it in the plate. These dishes were warmed in the dark at 20 ° C. for 48 hours until white mycelium was observed. These dishes were then continuously heated at 21 ° C. for 15-20 days under fluorescent lighting. The mycelium had a pink color at the end of the incubation period. Deionized water was placed in a sporulation dish and allowed to fill. The spores were scraped into water using a rubberized policeman. Water squeezing and scraping was repeated 2-3 times for each dish. The spore suspension was then filtered through a cheesecloth. Finally, the spore concentration was adjusted to 150-300 spores / m. Two drops of TWEEN 80 were added per 500 m of spore suspension. Optionally, the wheat plants of LEN were lightly sprayed with light oil and waited for 5 minutes, then the leaves were sprayed with spore suspension and TWEEN 80 using a manual sprayer to inoculate the spores. The inoculated plants were kept in a damp cabinet for 72 hours at 20 ° C with a photoperiod of 16 hours under light and 8 hours in the dark. The plants were then placed in the growing chamber under 16 hours of light / 8 hours in the dark for 7-9 days at 20 ° C. Then, the control% was evaluated. The test was performed using different dose ratios of the compounds. Table 8 shows the test results of the good compounds used in the test in the proportions of 3 types. When the compounds were tested at the same dose more than once, the average value was shown.<img file="JPH0655729B2_D0036.tif" /><img file="JPH0655729B2_D0037.tif" /><img file="JPH0655729B2_D0038.tif" />Comparative test Comparison between compounds 2 and 10 Comparison with compounds c2a, c2b and c10 Comparative trials of compounds 2, 10, c2a, c2b and c10 were performed in parallel for P. herpotrichoides and Septoria tritici in vitro. This test was carried out by the prescribed PDA poison agar as follows. Poison Agar Test 39 g of potato dextrose agar purchased from Difco was suspended in 1 water. The medium was autoclaved at 15 psi for 15 minutes. After autoclave sterilization, the medium was cooled for 15 minutes. A known amount of fungicide was then added to the molten agar to make serially diluted dilutions. The fungicide was dissolved in methanol, acetone, or DMSO before mixing with agar. After the next warming period, the degree of bacterial growth was evaluated. Pseudocercosporella herpotrichoides-12 days at room temperature Septoria tritici-14 days at room temperature The test result shows the radius in mm and EC<sub>75</sub>Was calculated. EC in ppm<sub>75</sub>The values were as follows.<img file="JPH0655729B2_D0039.tif" />Therefore, the compounds of the invention are at least 20 times more EC in less than the corresponding phenyl or benzyl compounds.<sub>75</sub>Had. Comparison of Compound 6 and Comparison Compound C6 In addition, a comparative comparison test between compound 2 and comparative compound C6 was conducted in vivo in parallel. Control of Barley Spot Blotch Acetone: Methanol: A high volume spray solution suspended in water was sprayed onto Pennrad barley saplings in a 3-inch pot using an overhead mechanical sprayer. EC<sub>75</sub>The values were calculated and the results are shown in Table 9 below. As shown in this table, the compounds of the invention, when treated on the day of inoculation, are at least 20 times more EC in less than the corresponding benzyl compounds.<sub>75</sub>Had. Control of Wheat Leaf Rust with Foliar Sprays by spraying on leaves The compound was suspended in acetone: methanol: water and sprayed using an overhead mechanical sprayer until it ran down into Pennol wheat in a 3-inch pot. These plants were inoculated with an aqueous suspension of summer spores (20,000 / m) of Puccinia recondita rust, kept warm at 70 ° F for 24 hours in a mist, and then in a greenhouse 7 I left it for a day. EC<sub>75</sub>The values were calculated and shown in Table 9 below. Controlling Wheat Powdery Mildew with Foliar Sprays by spraying on leaves Pennol wheat saplings in 3 inch pots were used to perform the prescribed spraying on the leaves. EC in ppm<sub>75</sub>The values were calculated and shown in Table 9 below.<img file="JPH0655729B2_D0040.tif" />As seen in the measurements in the table above, the compounds of the present invention clearly control barley spot blotch better than the comparative compounds. Compound 6 of the present invention may not be one of the good compounds for Wheat Leaf Rust or Wheat Powdery Mildew, And although the strength of the benzyl series is only against fungi against wheat, compound 6 is only somewhat lower than the comparative benzyl compound in controlling powdery mildew on wheat leaves, and compound 6 is wheat. For powdery mildew, it is good when inoculated on the day of treatment. Comparison of Compound 10 with Comparative Compound Controlling Wheat Powdery Mildew and Wheat Leaf Rust Comparative studies of Compound 10 and Comparative Compound 10 were performed twice in parallel in vivo using the experimental methods described earlier in Table 6.<img file="JPH0655729B2_D0041.tif" />Compound 10 is superior to the comparative compound against rust on wheat leaves, is good against powdery mildew on wheat, and is better than the comparative compound. In view of the comparative data, the phenethyl compound is generally superior to the corresponding benzyl and phenyl compounds . The compounds of the present invention include Wheat Foot Rot (Pseudocercosporella), Wheat Leaf Blotch (Septoria tritici), and Barley Spot Blotch (Barley Spot Blotch). Helminthosporium sativum] has one or more levels of goodness, generally Wheat Leaf Rust (Puccinia recondita) and Wheat Powdery Mildew (Erysiphe graminis). ] Is excellent. The obvious benefit of the Fenetyltriazole of the present invention is that it is comprehensively superior and effective against a large number of fungi. Preferred compounds of the present invention are Barley Spot Blight, Peanut Early Leaf spot, as well as good bactericidal activity against wheat leaf rust and wheat stalk rust. It also has good bactericidal activity against rice leaf blight (Rice Blast).
Every citation, both ways
| Document | Relation | Office |
|---|---|---|
| JP57114577A | Cites | Japan |
| JP5416474A | Cites | Japan |
47 members in 25 offices
Priority claims5
| Document | Office | Kind | Date |
|---|---|---|---|
| 88099086 | United States of America | A | |
| 88099086 | United States of America | A | |
| 880990 | – | – | – |
| 880990 | United States of America | – | – |
| US19860880990 | – | – | – |
Members47
| Document | Office | Kind | |
|---|---|---|---|
| DK336587D0 | Denmark | D0 | |
| IT8767565D0 | Italy | D0 | |
| PT85239A | Portugal | A | |
| GB8715388D0 | United Kingdom | D0 | |
| GB8723388D0 | United Kingdom | D0 | |
| IL83034A0 | Israel | A0 | |
| IL83034D0 | Israel | D0 | |
| IE871699L | Ireland | L | |
| DK336587A | Denmark | A | |
| ZA874751B | South Africa | B | |
| GB2192184A | United Kingdom | A | |
| AU7504887A | Australia | A | |
| DE3721786A1 | Germany | A1 | |
| EP0251775A2 | European Patent Office (EPO) | A2 | |
| JPS6322569A | Japan | A | |
| BR8703376A | Brazil | A | |
| HUT44415A | Hungary | A | |
| KR880001617A | Republic of Korea | A | |
| GB2197311A | United Kingdom | A | |
| FR2612741A1 | France | A1 | |
| EP0251775A3 | European Patent Office (EPO) | A3 | |
| IT1211468B | Italy | B | |
| IT8767565A0 | Italy | A0 | |
| TR23322A | Türkiye | A | |
| BE1001485A4 | Belgium | A4 | |
| PT85239B | Portugal | B | |
| GB2192184B | United Kingdom | B | |
| GB2197311B | United Kingdom | B | |
| NZ220916A | New Zealand | A | |
| AU607425B2 | Australia | B2 | |
| HU203452B | Hungary | B | |
| US5087635A | United States of America | A | |
| IL83034A | Israel | A | |
| EP0251775B1 | European Patent Office (EPO) | B1 | |
| AT84789T | Austria | T | |
| ATE84789T1 | Austria | T1 | |
| DE3783669D1 | Germany | D1 | |
| GR3006830T3 | Greece | T3 | |
| DE3783669T2 | Germany | T2 | |
| CA1321588C | Canada | C | |
| AR245448A1 | Argentina | A1 | |
| EG18875A | Egypt | A | |
| IE60314B1 | Ireland | B1 | |
| JPH0655729B2This record | Japan | B2 | |
| ES2053542T3 | Spain | T3 | |
| KR950003999B1 | Republic of Korea | B1 | |
| DK171399B1 | Denmark | B1 |
Numbers
- Publication
- 6-55729
- Publication, DOCDB
- H0655729
- Publication, EPODOC
- JPH0655729B
- Application
- 62165095
- Application, DOCDB
- 16509587
- Application, EPODOC
- JP19870165095
Titles2
- Japanese
- 【発明の名称】アルファ-アリ-ル-アルファ-フェニル-エチル-1H-1,2,4-トリアゾ-ル-1-プロパンニトリル化合物
- English
- [Title of Invention] Alpha-aryl-alpha-phenyl-ethyl-1H-1,2,4-triazo-l-1-propanenitrile compound
Classification
- CPC, 4
- C07D231/12
- C07D249/08
- A01N43/653
- C07D233/56
- IPC, 10
- A01N43 00
- A01N43 653
- C07D249 00
- C07D249 08
- C07D401 06
- C07D403 06
- E21D9 00
- C07D405 06
- C07D409 06
- C07D521 00