JPH02101067A - Novel acylated triazole derivative, production thereof and germicide for agricultural and horticulture containing the same derivative as active ingredient - Google Patents
Novel acylated triazole derivative, production thereof and germicide for agricultural and horticulture containing the same derivative as active ingredientInfo
- Publication number
- JPH02101067A JPH02101067A JP25305588A JP25305588A JPH02101067A JP H02101067 A JPH02101067 A JP H02101067A JP 25305588 A JP25305588 A JP 25305588A JP 25305588 A JP25305588 A JP 25305588A JP H02101067 A JPH02101067 A JP H02101067A
- Authority
- JP
- Japan
- Prior art keywords
- triazole derivative
- general formula
- formula
- agricultural
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003852 triazoles Chemical class 0.000 title claims abstract description 24
- 239000004480 active ingredient Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 230000002070 germicidal effect Effects 0.000 title abstract 2
- 238000003898 horticulture Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 239000000417 fungicide Substances 0.000 claims description 14
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- MZWDAEVXPZRJTQ-WUXMJOGZSA-N 4-[(e)-(4-fluorophenyl)methylideneamino]-3-methyl-1h-1,2,4-triazole-5-thione Chemical class CC1=NNC(=S)N1\N=C\C1=CC=C(F)C=C1 MZWDAEVXPZRJTQ-WUXMJOGZSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract description 4
- 241000607479 Yersinia pestis Species 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 230000001276 controlling effect Effects 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- 201000010099 disease Diseases 0.000 description 17
- 241000221785 Erysiphales Species 0.000 description 13
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- 235000021307 Triticum Nutrition 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
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- 230000005764 inhibitory process Effects 0.000 description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- -1 pyridine amines Chemical class 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000209094 Oryza Species 0.000 description 5
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- 235000009566 rice Nutrition 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 235000014443 Pyrus communis Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 241000221300 Puccinia Species 0.000 description 2
- 241000576755 Sclerotia Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 150000007980 azole derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000357297 Atypichthys strigatus Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
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- 241000282412 Homo Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- 241001518729 Monilinia Species 0.000 description 1
- 241001518731 Monilinia fructicola Species 0.000 description 1
- 241000498271 Necator Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000219998 Philenoptera violacea Species 0.000 description 1
- 241001618091 Phyllactinia pyri Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 241000157653 Psora Species 0.000 description 1
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- 208000010399 Wasting Syndrome Diseases 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
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- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、植物病害を防除する作用を有する活性成分と
しての有用性を有するアシル化トリアゾール誘導体とそ
の製造法及び該アシル化ｉ・リアゾール誘導体を活性成
分として含有する農園芸用殺菌剤に関する。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to an acylated triazole derivative useful as an active ingredient having the action of controlling plant diseases, a method for producing the same, and a method for producing the acylated i-lyazole derivative. This invention relates to an agricultural and horticultural fungicide contained as an ingredient.
従来の技術
現在、種々の植物病害の農作物に与える損害は莫大なも
のがあり、また農薬による環境汚染の問題も屡話題とし
て取り上げられ、人々の関心を集めてきた。従って、人
畜、鳥類及び魚類に対する毒性が低く、有用植物に対す
る薬害の少い、即取扱い上での安全性が高く環境に対す
る影響が少く、しかも広範な植物病害に対して優れた防
除効果を示す農園芸用殺菌剤が求められてきた。BACKGROUND OF THE INVENTION At present, various plant diseases cause enormous damage to agricultural crops, and the problem of environmental pollution caused by pesticides has often been brought up as a topic of discussion and has attracted people's attention. Therefore, it has low toxicity to humans, livestock, birds, and fish, has little phytotoxicity to useful plants, is highly safe for immediate handling, has little impact on the environment, and has excellent control effects against a wide range of plant diseases. Horticultural fungicides have been sought after.
このような農園芸用殺菌剤としてトリアゾール誘導体が
すぐれた効果を有することが示されている。（特開昭６
２−１４９６６７、特開昭６３−１５６７８２゜）本発
明者等は更に人畜等に対する毒性が低く取り扱い上での
安全性が高く、かつ広範な植物病害に対して優れた防除
効果を示すアゾール誘導体について研究を行い、多数の
アゾール誘導体を合成し、それらの実用性について検討
を行った結果、アシル化トリアゾール誘導体が上述した
特性を有することを見出し、本発明をなすに至った。It has been shown that triazole derivatives have excellent effects as such agricultural and horticultural fungicides. (Unexamined Japanese Patent Publication No. 6
2-149667, Japanese Patent Application Laid-Open No. 63-156782゜) The present inventors have further developed an azole derivative that has low toxicity to humans and livestock, is highly safe to handle, and has excellent control effects against a wide range of plant diseases. As a result of conducting research, synthesizing a large number of azole derivatives, and examining their practicality, it was discovered that acylated triazole derivatives have the above-mentioned properties, leading to the present invention.
すなわち、本発明の目的は、農園芸用殺菌剤の活性成分
として有用な新規アシル化トリアゾール誘導体とその製
造法及び該アシル化］・リアゾール誘導体を活性成分と
して含有する床孔な植物病害に対して優れた防除効果を
奏する農園芸用殺菌剤を提供することにある。That is, the purpose of the present invention is to provide a novel acylated triazole derivative useful as an active ingredient of an agricultural and horticultural fungicide, a method for producing the same, and a method for treating the diseases of porous plants containing the acylated lyazole derivative as an active ingredient. An object of the present invention is to provide an agricultural and horticultural fungicide that exhibits an excellent pest control effect.
問題点を解決するための手段
本発明は
■ 下記一般式（Ｉ）で示されるアシル化トリアゾール
誘導体と
（式中、Ｘはハロゲン原子、Ｃ１〜４のアルキル基、フ
ェニル基を表わす。またＲはＣ１〜３のアルキル基を表
わす。）
■ 下記一般式（ｎ）で示されるトリアゾール誘導体を
（式中、Ｘはハロゲン原子、０１〜４のアルキル基、フ
ェニル基を表わす。）
触媒の存在下に下記一般式（１１）で示される酸無水物
とを反応させることにより上記一般式（Ｉ）で示される
アシル化トリアゾール誘導体を製造する方法
Ｒ−Ｇｏ−０−Ｇｏ−Ｒ（１）
（式中、Ｒは０１〜３のアルキル基を表わす。）及び
■ 上記一般式（Ｉ＞で示されるアシル化トリアゾール
誘導体を活性成分として含有する農園芸用殺菌剤である
。Means for Solving the Problems The present invention provides (1) an acylated triazole derivative represented by the following general formula (I) (wherein X represents a halogen atom, a C1-4 alkyl group, or a phenyl group; (Represents a C1-3 alkyl group.) ■ A triazole derivative represented by the following general formula (n) (wherein, X represents a halogen atom, an alkyl group of 01-4, or a phenyl group) in the presence of a catalyst. A method for producing an acylated triazole derivative represented by the above general formula (I) by reacting with an acid anhydride represented by the following general formula (11) R-Go-0-Go-R (1) (in the formula , R represents an alkyl group of 01 to 3) and (2) This is an agricultural and horticultural fungicide containing an acylated triazole derivative represented by the above general formula (I>) as an active ingredient.
本発明に係る上記アシル化トリアゾール誘導体は文献未
載の新規化合物であって、それを例示すると表１に示す
とおりであるが、これに限定されるものではない。The above-mentioned acylated triazole derivative according to the present invention is a new compound that has not been described in any literature, and examples thereof are shown in Table 1, but the invention is not limited thereto.
その理化学的性質を表１に併記する。Its physical and chemical properties are also listed in Table 1.
表１に示した各化合物のＮＭＲスペクトルはＴＭＳを内
部基準にして測定し、下記の記号で示した。The NMR spectra of each compound shown in Table 1 were measured using TMS as an internal standard, and are indicated by the following symbols.
Ｓ・・・−重線、ｄ・・・二重線、ｔ・・・三重線、ｍ
・・・多重線、ｂ・・・ブロードライン、Ｊ・・・カッ
プリング定数（単位、Ｈｚ＞
なお、表１に例示した各化合物の赤外吸収スペクトルを
添付図（第１図〜第〆図）に示した。S...- double line, d... double line, t... triple line, m
...Multiple line, b...Broad line, J...Coupling constant (unit, Hz> )It was shown to.
本発明に係る上記の一般式（Ｉ＞で示されるアシル化ト
リアゾール誘導体は下記方法により製造される。The acylated triazole derivative represented by the above general formula (I>) according to the present invention is produced by the following method.
前記一般式（Ｉ［）で示されるトリアゾール誘導体を希
釈剤および触媒の存在下に、前記一般式（ＩＩ）で示さ
れる酸無水物と反応させることにより、前記一般式（Ｉ
）で示される目的のアシル化トリアゾール誘導体が冑ら
れる。By reacting the triazole derivative represented by the general formula (I[) with the acid anhydride represented by the general formula (II) in the presence of a diluent and a catalyst, the triazole derivative represented by the general formula (I
) The desired acylated triazole derivative is obtained.
ここで出発物質として用いる一般式（ｎ）で示されるト
リアゾール誘導体は、公知化合物であって、特開昭６２
−１４９６６７に記載されている化合物が使用され得る
。The triazole derivative represented by the general formula (n) used here as a starting material is a known compound,
-149667 can be used.
本発明に係る一般式（Ｉ）で示される化合物は一般式（
ｎ）および一般式（ＩＩＩ）で示される化合物を希釈剤
の存在で反応させることが好ましい。The compound represented by the general formula (I) according to the present invention is a compound represented by the general formula (I).
n) and the compound represented by general formula (III) are preferably reacted in the presence of a diluent.
一般式（ｎ）で示される化合物としては無水酢酸。The compound represented by general formula (n) is acetic anhydride.
無水プロピオン酸、無水酪酸等が好ましく使用される。Propionic anhydride, butyric anhydride, etc. are preferably used.
希釈剤としてはベンゼン、トルエン、キシレン、ヘキサ
ン等の炭化水素類；塩化メチレン。Diluents include hydrocarbons such as benzene, toluene, xylene, and hexane; methylene chloride.
クロロホルム、四塩化炭素等のハロゲン化炭化水素類；
ジエチルエーテル、ジイソプロピルエーテル、テトラヒ
ドロフラン等のエーテル類を例示し得る。Halogenated hydrocarbons such as chloroform and carbon tetrachloride;
Examples include ethers such as diethyl ether, diisopropyl ether, and tetrahydrofuran.
希釈剤を使用せず一般式（ＩＩＩ）で示される酸無水物
を溶媒として利用するということも可能である。It is also possible to use the acid anhydride represented by the general formula (III) as a solvent without using a diluent.
この場合には一般式（Ｉ［［＞で示される酸無水物を適
当に過剰量使用する必要がある。In this case, it is necessary to use an appropriate excess amount of the acid anhydride represented by the general formula (I[[>).
なお、本発明に係る一般式（Ｉ）の製造法では例えばｉ
・リエチルアミン、ピリジン、Ｎ、Ｎ−ジメチル−４−
ピリジンアミンの如ぎ触媒を使用することが好ましく、
特にトリエチルアミンとＮ、Ｎジメチル−４−ピリジン
アミンの両者を併用することが好ましい。In addition, in the method for producing general formula (I) according to the present invention, for example, i
・Ethylamine, pyridine, N,N-dimethyl-4-
Preferably, catalysts such as pyridine amines are used;
In particular, it is preferable to use both triethylamine and N,N dimethyl-4-pyridineamine in combination.
本発明に係る製造法を実施するには例えば前記般式（ｎ
）で示されるトリアゾール類を前記の希釈剤に溶かした
ものに前記一般式（Ｉ［）で示される酸無水物を一般式
（ＩＩ＞で示される化合物に対して１．０〜３．０当吊
、前記の触媒を０．０４〜２．０当量それぞれ加えて反
応させることが好ましい。To carry out the production method according to the present invention, for example, the general formula (n
) is dissolved in the diluent described above, and the acid anhydride represented by the general formula (I It is preferable to add 0.04 to 2.0 equivalents of each of the above catalysts and react.
また前記の希釈剤の代わりに、前記一般式（Ｉ［［＞で
示される酸無水物を用いてもよい。Further, instead of the diluent described above, an acid anhydride represented by the general formula (I[[>) may be used.
この際の反応温度は溶媒としての希釈剤の凝固点から沸
点までの任意の温度を適用し得るが、０℃乃至５０℃の
範囲の温度で反応を行うことが好ましい。また反応時間
は１０〜３０時間の範囲であって、撹拌下に反応を行う
ことが好ましい。The reaction temperature at this time may be any temperature from the freezing point to the boiling point of the diluent as a solvent, but it is preferable to carry out the reaction at a temperature in the range of 0°C to 50°C. Moreover, the reaction time is in the range of 10 to 30 hours, and it is preferable to carry out the reaction while stirring.
上記反応の終了後、得られた反応混合物を、氷水中に注
ぎ、酢酸エチル、クロロホルム、ベンゼン等の有機溶剤
により抽出して有機層を分離し、次いで該有機層を酸水
溶液、アルカリ水溶液、飽和食塩水でそれぞれ洗浄して
乾燥した後、溶媒を減圧下に留去し、得られた残漬を精
製処理することにより、目的とする化合物を得る。なお
精製処理はシリカゲルカラムクロマトグラフィー等に付
することにより行い得る。After the completion of the above reaction, the obtained reaction mixture was poured into ice water and extracted with an organic solvent such as ethyl acetate, chloroform, or benzene to separate the organic layer. After washing with brine and drying, the solvent is distilled off under reduced pressure, and the resulting residue is purified to obtain the desired compound. Note that the purification treatment can be performed by subjecting it to silica gel column chromatography or the like.
次に、本発明に係る前記一般式（Ｉ＞を有するアシル化
トリアゾール誘専体の農園芸用殺菌剤の活性成分として
の有用性について説明する。Next, the usefulness of the acylated triazole derivative having the general formula (I>) as an active ingredient of the agricultural and horticultural fungicide according to the present invention will be explained.
上記アシル化］・リアゾール誘導体は下記に示す広範囲
な植物病害に対して優れた防除効果を奏する。The above acylated lyazole derivatives exhibit excellent control effects against a wide range of plant diseases listed below.
イネのいもち病（Ｐｙｒｉｃｕｌａｒｉａ ｏｒｙｚａ
ｅ）、イネのごま葉枯病（Ｃｏｃｈｌｉｏｂｏｌｕｓ
ｎ＋１ｙａｂｅａｎｕｓ）、イネの白菜枯病（Ｘ ａｎ
ｔｈｏｌｌｏｎａｓ ｏｒｙｚａｅ）、イネの紋枯病（
Ｒｈｉｚｏｃｔｏｎｉａ ５ｏｌａｎｉ）、イネの小黒
菌核病（＠ ｅｌＩ＋ｎｔｈｏＳｐｏｒ＋ｕｌｓｉｇｎ
ｏｉｄｅｕｎｌ）、
イネの馬鹿苗病（Ｇ １ｂｂｅｒｅｌｌａ ｆｕｊｉｋ
ｕｒｏｉ）、リンゴのうどんこ病（Ｐｏｄｏｓｐｈａｅ
ｒａ １ｅｕｃｏｔｒ＋ｃｈａ）リンゴの黒星病（Ｖｅ
ｎｔｕｒｉａ １ｎａｅＱＩＪａｌｉｓ）、リンｊ（７
）モニｌＪ７病（Ｍｏｎｉｌｉｎｉａ １ａｌｉ）、リ
ンゴの斑点落葉病（Ａ １ｔｅｒｎａｒｉａ １１ａｌ
ｉ）、リンゴの腐らん病（Ｖ ａｌｓａ １Ｉｌａｌｉ
）、ナシの黒斑病（Ａ １ｔｅｒｎａｒｉａ ｋｉｋｕ
ｃｈｉａｎａ）、ナシ（１）うどんこ病（Ｐｈｙｌｌａ
ｃｔｉｎｉａ ｐｙｒｉ）、ナシの赤星病（Ｑ ｙ１１
１ｎＯ３ｐＯｒａｎ（ｌｉｕｌｌ ａｓｉａｔｉｃｕｌ
ｌｌ）、ナシの黒星病（Ｖ ｅｎｔｕｒｉａ ｎａｓｈ
ｉｃｏｌａ）、ブドウのうどんこ病（Ｕ ｎｃｉｎｕｌ
ａ ｎｅｃａｔｏｒ）、ブドウのさび病（Ｐ ｈａｋｏ
ｐｓｏｒａ ａｎｐｅｌｏｐｓｉｄｉｓ）、ブドウの晩
成病（Ｇ １ｏｎｅｒｅｌｌａ ｃｉｎｇｕｌａｔａ）
、オオムギのうどんこ病（Ｅ ｒｙｓｉｐｈｅ ｇｒａ
ｎｉｎｉｓｆ、 ｓｐ浦０ｒｄｅｉ）、
オオムギの雲形病（Ｒｈｙｎｃｈｏｓｐｏｒｉｕｌｌｓ
ｅｃａｌｉｓｆ、ｓｐ、ｈｏｒｄｅｉ）、
オオムギの黒さび病（Ｐｕｃｃｉｎｉａ ｇｒａｌｎｉ
ｓ）、オオムギの黄さび病（Ｐｕｃｃｉｎｉａ ５ｔｒ
ｉｉｆｏｒｒＲｉｓ）、コムギの赤さび病（Ｐｕｃｃｉ
ｎｉａ ｒｅｃｏｎｄｉｔａ）、コムギの葉枯病（Ｓｅ
ｐｔｒｉａ ｔｒｉｔｉｃｉ）、コムギの黄さび病（ｐ
ｕｃｃｉｎｉａ ５ｔｒｉｉｆｏｒ１１ｉｓ）、コムギ
のうどんこ病（Ｅ ｒｙｓｉｐｈｅ ｇｒａｌｉｎｉｓ
ｆ、ｓｐ、ｔｒｉｔｉｃｉ）、
ウリ類のうどんこ病（Ｓｐｈａｅｒｏｔｈｅｃａ ｆｕ
ｌｉｑｉｎｅａ）、ウリ類の炭そ病（Ｃｏｌｌｅｔｏｔ
ｒｉｃｈｕＩｌｌａｇｅｎａｒｉｃｖ）、スイカのつる
割病（Ｆ ｕｓａｒｉｕｎ ｏｘｙｓｐｏｒｕｎｆ、ｓ
ｐ、ｎ１ｖｅｕ１１）、
キュウリのつる割病（「ｕｓａｒｉｕｎ ｏｘｙｓｐｏ
ｒｕｎｆ、ｓｐ、ｃｕｃｕｍｅｒｉｎｕｎ） 、ダイ
コンの萎黄病（Ｆ ｕｓａｒｉｕｎ ｏｘｓｐｏｒｕｍ
ｆ、 ｓｐ、 ｒａｐｈａｎ ｉ ） 、１〜７１〜
のうどんこ病（Ｅ ｒｙｓｉｐｈｅ ｃｉｃｈｏｒａｃ
ｅａｒｕＩ）、］・マドの輪紋病（Ａ １ｔｅｒｎａｒ
ｉａ ５ｏｌａｎｉ）、ナスのうどんこ病（Ｅ ｒｙｓ
ｉｐｈｅ ｃｉｃｈｏｒａｃｅａｒｕｎ）、イチゴのう
どんこ病（３ｐｈａｅｒｏｔｈｅｃａ ｈｕｌｕ ｌ
ｉ ）、タバコのうどんこ病（Ｅ ｒｙｓｉｐｈｅ ｃ
ｉｃｈｏｒａ−ｃｅａｒｕｌ）、
タバコのみ星病（Ａ １ｔｅｒｎａｒｉａ ｌｏｎｇｉ
ｐｅｓ）、テンサイの褐斑病（Ｃｅｒｃｏｓｐｏｒａ
ｂｅｔｉｃｏｌａ＞、ジャガイモの夏痩病（ＡＩｔｅｒ
ｎａｒｉａ ５ｏｌａｎｉ）、ダイスの褐紋病（Ｓ ｅ
ｐｔｏｒｉａ ｇｌｙｃｉｎｅｓ）、ダイスの紫斑病（
Ｑｅｒｃｏｓｐｏｒａ ｋｉｋｕｃｈｉ）、核果類果樹
の灰星病（Ｍｏｎｉｌｉｎｉａ ｆｒｕｃｔｉｃｏｌａ
）、種々の作物をおかず灰色かび病（Ｂｏｔｒｙｔｉｓ
ｃｉｎｅｒｅａ ）及び
菌核病（３ｃｌｅｒｏｔｉｎｉａ ５ｃｌｅｒｏｔｉｏ
ｒｕｎ）などに対して活性を有する。Rice blast disease (Pyricularia oryza)
e) Sesame leaf blight of rice (Cochliobolus
n+1yabeanus), Chinese cabbage blight of rice (X an
thollonas oryzae), rice sheath blight (
Rhizoctonia 5olani), small black sclerotia of rice (@elI+nthoSpor+ulsign
G1bberella fujik (G1bberella fujik)
uroi), apple powdery mildew (Podosphae
ra 1eucotr+cha) Apple scab disease (Ve
nturia 1naeQIJalis), Linj (7
) Monilinia 1ali, apple leaf spot leaf disease (A 1ternaria 11al)
i), apple rot (V alsa 1Ilali)
), pear black spot (A 1ternaria kiku)
chiana), pear (1) powdery mildew (Phylla
ctinia pyri), pear red star disease (Q y11
1nO3pOran(liull asiaticul
ll), V enturia nash
icola), powdery mildew of grapes (Uncinul
a necator), grape rust (P hako
psora ampelopsidis), grape late disease (G onenerella cingulata)
, powdery mildew of barley (E rysiphe gra
nisf, spura0rdei), barley cloud disease (Rhynchosporiulles)
ecalisf, sp, hordei), barley rust (Puccinia gralni)
s), barley yellow rust (Puccinia 5tr
iiforrRis), wheat rust (Pucci
nia recondita), wheat leaf blight (Se
ptria tritici), wheat yellow rust (p.
uccinia 5triifor11is), wheat powdery mildew (E rysiphe gralinis)
f, sp, tritici), powdery mildew of cucurbits (Sphaerotheca fu
liqinea), anthracnose of cucurbits (Colletot
watermelon oxysporunf, s
p, n1veu11), cucumber vine disease (usariun oxyspo
runf, sp., cucumerinun), radish chlorosis (Fusariun oxsporum)
f, sp, raphan i), 1~71~
powdery mildew (E rysiphe cichorac)
earuI), ]・ Mado ringtone disease (A 1ternar)
ia 5olani), powdery mildew of eggplant (E rys
iphe cichoracearun), strawberry powdery mildew (3phaerotheca hulu l)
i), powdery mildew of tobacco (E rysiphe c)
ichora-cearul), Tobacco only star disease (A 1ternaria longi)
pes), sugar beet brown spot (Cercospora
beticola>, potato summer wasting disease (AIter)
naria 5olani), Dice brown spot (S e
ptoria glycines), Dice purpura (
Qercospora kikuchi), Monilinia fructicola of stone fruit trees
), gray mold disease (Botrytis) that affects various crops as a side dish
cinerea) and sclerotia (3clerotinia 5clerotio)
It has activity against such things as run).
前記一般式（Ｉ＞で示されるアシル化トリアゾール誘導
体の化合物を＠園芸用殺菌剤として適用するには、該化
合物をそのまま、又は担体（希釈剤）と混合して粉剤、
水和剤、粒剤、乳剤、ならびに液剤等の形態として有利
に使用し得る。更に、必要に応じて上記担体のほかに展
着剤、乳化剤、湿展剤、固着剤等の助剤を添加すること
により効果を−Ｍ１１実にすることも勿論可能である。In order to apply the acylated triazole derivative compound represented by the general formula (I>) as a horticultural fungicide, the compound can be used as it is or mixed with a carrier (diluent) to form a powder,
It can be advantageously used in the form of wettable powders, granules, emulsions, liquids, and the like. Furthermore, it is of course possible to increase the effect to -M11 by adding auxiliary agents such as a spreading agent, an emulsifying agent, a wetting agent, and a fixing agent in addition to the above-mentioned carrier, if necessary.
担体（希釈剤）及び助剤の種類、アシル化トリアゾール
誘導体との混合比は広い範囲において選択することがで
きる。The type of carrier (diluent) and auxiliary agent and the mixing ratio with the acylated triazole derivative can be selected within a wide range.
囚に、本化合物は、１，２．４−トリアゾール環を含有
しているので、無機酸塩、有機酸塩もしくは金属錯塩等
の形態でも使用し得る。Additionally, since the present compound contains a 1,2,4-triazole ring, it can also be used in the form of an inorganic acid salt, an organic acid salt, a metal complex salt, or the like.
また、本化合物には、シクロペンタン骨格の１位と２位
に不斉炭素が存在するので、シス体とトランス体の幾何
異性体ならびに光学異性体等の立体異性体が存在し得る
が、本発明ではこれら全ての単独の異性体ならびに各異
性体の任意の比率での混合物をも包含するものである。In addition, since this compound has asymmetric carbon atoms at the 1st and 2nd positions of the cyclopentane skeleton, it may exist in stereoisomers such as cis and trans geometric isomers and optical isomers. The invention includes all these individual isomers as well as mixtures of each isomer in any ratio.
したがって、本発明に係る農園芸用殺菌剤は、これら異
性体の単独又は、混合物を活性成分として含有するもの
を包含するものであると理解すべきである。Therefore, it should be understood that the agricultural and horticultural fungicides according to the present invention include those containing these isomers alone or in mixtures as active ingredients.
及週１と夾星
本発明のアシル化トリアゾール誘導体は一般式（ＩＦ）
のＯＩ−１基をＲＣＯ基に置換した新規なトリアゾール
誘導体である。これらの化合物はそのまま、又は各種担
体と混合し種々の形態で農園芸用殺菌剤として使用する
ことができる。本発明の農園芸用殺菌剤は後記の実施例
から明らかなように、極めて広範囲の植物病害に対して
すぐれた防除効果を奏する。しかも植物病害のうち、い
くつかの病害に対しては予防的な防除効果のみならず治
療的効果をも奏する。The acylated triazole derivative of the present invention has the general formula (IF)
This is a novel triazole derivative in which the OI-1 group of is substituted with an RCO group. These compounds can be used as agricultural and horticultural fungicides as they are or in various forms mixed with various carriers. As is clear from the examples below, the agricultural and horticultural fungicide of the present invention has excellent control effects against a wide range of plant diseases. Moreover, it has not only a preventive control effect but also a therapeutic effect against some plant diseases.
以下、本発明に係るアシル化トリアゾール誘導体の具体
的な製造法及び該誘導体を活性成分として利用した農園
芸用殺菌剤の具体例を示してその効果を説明する。Hereinafter, a specific method for producing the acylated triazole derivative according to the present invention and a specific example of an agricultural and horticultural fungicide using the derivative as an active ingredient will be shown and the effects thereof will be explained.
実施例１
ｃｍ２−（（４−クロロフェニル）メチル１−１−（Ｉ
Ｈ−１，２，４−トリアゾール−１−イルメチル）ｒ
−１−シクロペンチルアセテート（表１に示した番号１
の化合物）の製造
ｃ−２−［（４−クロロフェニル）メチル］−１−（１
Ｈ−１，２，４−トリアゾール−１−イルメチル）ｒ−
１−シクロペンタノール５００■に、無水酢酸０．６ｄ
、 ｌ−リエチルアミン０．６ｄ、Ｎ、Ｎ−ジメチル
−４−ピリジンアミン１６ｆｆｇをそれぞれ加え、室温
で１４時間撹拌した。Example 1 cm2-((4-chlorophenyl)methyl 1-1-(I
H-1,2,4-triazol-1-ylmethyl)r
-1-cyclopentyl acetate (number 1 shown in Table 1)
Preparation of c-2-[(4-chlorophenyl)methyl]-1-(1
H-1,2,4-triazol-1-ylmethyl)r-
1-cyclopentanol 500μ, acetic anhydride 0.6d
, 0.6 d of l-ethylamine, and 16 ffg of N,N-dimethyl-4-pyridinamine were added, and the mixture was stirred at room temperature for 14 hours.
得られた反応混合物を氷水中に注ぎ、酢酸エチルで抽出
して有機層を得、該有機層を１Ｎ塩酸。The resulting reaction mixture was poured into ice water and extracted with ethyl acetate to obtain an organic layer, which was then diluted with 1N hydrochloric acid.
飽和炭酸水素す］・リウム水溶液、飽和食塩水でそれぞ
れ洗浄した後、無水硫酸ナトリウムで乾燥し、次いで減
圧下に溶媒を留去した。After washing with a saturated aqueous solution of hydrogen carbonate and saturated brine, it was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
得られた残漬をシリカゲルカラムクＯマドグラフィー（
展開溶媒：ｎ−ヘキサン：酢酸エチル−１：１）に付し
て精製し、標題化合物２７０１１５＋を得た。（収率４
り、６％）
このようにして得られた化合物のＮＭＲスペクトルデー
ターを１表に、赤外吸収スペクトルを第１図に示す。The resulting residue was subjected to silica gel column O-madography (
Purification was performed using n-hexane:ethyl acetate (developing solvent: 1:1) to obtain the title compound 270115+. (yield 4
(6%) The NMR spectrum data of the compound thus obtained are shown in Table 1, and the infrared absorption spectrum is shown in FIG.
実施例２
ｃｍ２−［（４−クロロフェニル）メチル］−１−（Ｉ
Ｈ−１，２，４−トリアゾール−１−イルメチル）ｒ
−１−シクロペンチルプロピオネート（表１に示した番
号６の化合物）の製造
ｃ−２−［（４−クロロフェニル）メチル］−１−（１
日−１，２，４−トリアゾール−１−イルメチル）−ｒ
−１−シクロペンタノール５００ＩＲｇに、無水プロピ
オン酸０．５−、トリエチルアミン０．５ｉ、 Ｎ、
Ｎジメチル−４−ピリジンアミンｉｏｍｇをそれぞれ加
え、室温で２５時間撹拌した。Example 2 cm2-[(4-chlorophenyl)methyl]-1-(I
H-1,2,4-triazol-1-ylmethyl)r
-Production of 1-cyclopentylpropionate (compound number 6 shown in Table 1) c-2-[(4-chlorophenyl)methyl]-1-(1
-1,2,4-triazol-1-ylmethyl)-r
-1-Cyclopentanol 500IRg, propionic anhydride 0.5-, triethylamine 0.5i, N,
N dimethyl-4-pyridinamine iomg was added to each and stirred at room temperature for 25 hours.
得られた反応混合物を氷水中に注ぎ、酢酸エチルで抽出
して有機層を得、該有機層を１Ｎ塩酸。The resulting reaction mixture was poured into ice water and extracted with ethyl acetate to obtain an organic layer, which was then diluted with 1N hydrochloric acid.
飽和炭酸水素ナトリウム水溶液、飽和食塩水でそれぞれ
洗浄した後、無水硫酸ナトリウムで乾燥し、次いで減圧
下に溶媒を留去した。After washing with saturated aqueous sodium hydrogen carbonate solution and saturated brine, it was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
得られた残渣をシリカゲル力ラムクロマトグラフィーに
付して精製し、標題化合物３３０１８９を得た。The obtained residue was purified by silica gel column chromatography to obtain the title compound 330189.
（収率５５．９％）。(Yield 55.9%).
このようにして冑られた化合物のＮＭＲスペクトルデー
ターを１表に、赤外吸収スペクトルを第６図に示す。The NMR spectrum data of the compound thus removed is shown in Table 1, and the infrared absorption spectrum is shown in FIG.
次に、上記アシル化トリアゾール誘導体を活性成分とし
て含有する農園芸用殺菌剤の製剤処方及実施例４：水和
剤
び病原菌防除試験例を示す。Next, the formulation of an agricultural and horticultural fungicide containing the above-mentioned acylated triazole derivative as an active ingredient and Example 4: Wettable powder and pathogen control test example will be shown.
実施例３：粉 剤
重量部
本発明化合物（化合物番号１） ５０リグニンスルホ
ン酸塩 ５アルキルスルホン酸塩
３珪 藻 土
４２を粉砕混合して水和剤とし、水で希釈して
使用する。Example 3: Parts by weight of powder Compound of the present invention (compound number 1) 50 Lignin sulfonate 5 Alkyl sulfonate
3 Diatomaceous earth
42 is ground and mixed to make a wettable powder, which is diluted with water and used.
実施例５：粒 剤
重量部
本発明化合物（化合物番号１）３
り し −
４ 。Example 5: Parts by weight of granules Compound of the present invention (compound number 1) 3 -
4.
タ ル り
５７を粉砕混合し、散粉として使用する。Tarri
57 was ground and mixed and used as powder.
重量部
本発明化合物（化合物番号３）５
ベントナイト ４３り し
− ４５
リグニンスルホンＩＩ塩 ７を均一に混合
し更に水を加えて練り合わせ、押し出し式造粒機で粒状
に加工乾燥して粒剤とする。Parts by weight Compound of the present invention (compound number 3) 5 Bentonite 43
-45
The lignin sulfone II salt 7 is uniformly mixed, water is added and kneaded, and the mixture is processed into granules using an extrusion granulator and dried to form granules.
実施例６：乳 剤
接種から７〜１０日後にコムギ赤さび病の病斑面積重量
部
率を調査し、下記式により防除価を算出した。Example 6: Seven to ten days after emulsion inoculation, the area weight percentage of wheat rust was investigated, and the control value was calculated using the following formula.
本発明化合物（化合物番号６） ２０ポリオキシエチ
レンアルキル
アリルエーテル
無散布区の病斑面積率
ポリオキシエチレンソルビタ
ンモノラウレート ３結果は表２に示
す。Compound of the present invention (Compound No. 6) 20 Lesion area ratio polyoxyethylene sorbitan monolaurate in plots without polyoxyethylene alkyl allyl ether spraying 3 The results are shown in Table 2.
キ シ し ン
６７を均一に混合溶解して乳剤とする。Kishin
67 is uniformly mixed and dissolved to form an emulsion.
実施例７：コムギ赤さび病防除試験
径１０ａｎの素焼鉢を用いて栽培した第２葉期の幼苗コ
ムギ（品種；農林６４号、１６本／鉢）に、実施例４に
示した水和剤形態のものを水で所定濃度に希釈懸濁し、
５威／鉢の割合で散布した。散布菜風乾後、り病巣より
採取したコムギ赤さび病菌夏胞子の懸濁液を噴霧接種し
２０〜２３℃高湿度条件下に２４時間保った。その後ガ
ラス温室内に放置し、実施例８：コムギうどんこ病防除
試験
径１０ｃＩｎの素焼鉢を用いて栽培した第２葉期の幼苗
コムギ（品種：農林６４号、１６本／鉢、３鉢 処理区
使用）に、実施例４の如き水和剤形態のものを所定濃度
に水で希釈懸濁し、１鉢当り５威散布した。散布葉風乾
後、り病巣から採取したコムギうどんこ病菌胞子の懸濁
液を噴霧接種し、２０〜２４℃高湿度条件下に２４時間
保ちその後は温室内に放置した。接種後９〜１１日目に
コムギうどんこ病の病斑面積率を調査し、下記式により
防除価を算出した。Example 7: Test for controlling wheat rust dilute and suspend with water to a predetermined concentration,
Sprayed at a rate of 5 per pot. After spraying and air-drying, a suspension of naspores of the wheat rust fungus, collected from the lesions, was spray inoculated and kept at 20-23°C under high humidity conditions for 24 hours. After that, they were left in a glass greenhouse, and Example 8: Wheat Powdery Mildew Control Test Second leaf stage seedlings of wheat (variety: Norin No. 64, 16 plants/pot, 3 pots) grown using clay pots with a diameter of 10 cIn. A wettable powder as in Example 4 was diluted and suspended in water to a predetermined concentration, and sprayed at 5 doses per pot. After spraying and air-drying the leaves, the leaves were spray-inoculated with a suspension of wheat powdery mildew spores collected from the lesions, and kept under high humidity conditions of 20-24°C for 24 hours, after which they were left in a greenhouse. The lesion area ratio of wheat powdery mildew was investigated 9 to 11 days after inoculation, and the control value was calculated using the following formula.
無散布区の病斑面積率 結果は表３に示す。Lesion area rate in non-sprayed area The results are shown in Table 3.
実施例９
各種病原菌に対する抗菌性試験
本例は、本発明によるアゾール誘導体の化合物の各種植
物病原菌に対する抗菌性を試験した結果を示したもので
ある。Example 9 Antibacterial activity test against various pathogenic bacteria This example shows the results of testing the antibacterial activity of the azole derivative compound according to the present invention against various plant pathogenic bacteria.
試験方法：
本発明化合物を、所定濃度となるように、Ｄｉｎ＋ｅｔ
ｈｙｌ ５ｕｌｆｏｘｉｄｅに溶解し、その０．６蛇と
、６０℃前後のＰＳＡ培地６０ｄを１００ｄ三角フラス
コ内でよく混合し、シャーレ内に流し固化させた。一方
、予め平板培地上で培養した供試菌を直径４ ｒａｍの
コルクポーラ−でうちぬき、上記の薬剤含有平板培地上
に接種した。接種後、８菌の生育適温にて１〜３日間培
養し、菌の生育を菌そう直径で測定し、薬剤無添加区に
おける菌の生育と比較して下記式に従い菌糸伸長抑制率
を求めた。Test method: The compound of the present invention was added to a predetermined concentration in Din+et
The 0.6 volume dissolved in hyl 5ulfoxide and 60 d of PSA medium at around 60° C. were mixed well in a 100 d Erlenmeyer flask, and poured into a petri dish to solidify. On the other hand, a test bacterium cultured in advance on a plate medium was punched out with a cork polar having a diameter of 4 ram, and inoculated onto the drug-containing plate medium. After inoculation, the 8 bacteria were cultured for 1 to 3 days at a temperature suitable for growth, and the growth of the bacteria was measured by the diameter of the fungi.The growth of the bacteria was compared with the growth in the area without the addition of chemicals, and the inhibition rate of hyphal elongation was determined according to the following formula. .
Ｒ＝（ｄｃ−ｄｔ） １００／ｄｃ 式中 Ｒ−菌糸伸長抑制率（％） ｄｃ−無処理平板上筒そう直径 ｄｔ−薬剤処理平板上筒そう直径 をそれぞれ示す。R=(dc-dt) 100/dc In the formula: R-hyphal elongation inhibition rate (%) dc-Untreated flat plate upper cylinder diameter dt-Diameter of drug treatment flat plate upper cylinder are shown respectively.
結果を次の基準に従って生育阻害度を５段階評価し、表
４に示した。The results are shown in Table 4, where the degree of growth inhibition was evaluated in five stages according to the following criteria.
生育阻害度
５ 菌糸伸長抑制率が１００％〜９０％以上のも
の
４ 菌糸伸長抑制率が ９０％未満〜７０％以上
のもの
３ 菌糸伸長抑制率が ７０％未満〜４０％以上
のもの
菌糸伸長抑制率が
％以上のもの
４０％未満〜２０
菌糸伸長抑制率が
２０％未満のもGrowth inhibition degree 5 Mycelial elongation inhibition rate is 100% to 90% or more 4 Mycelial elongation inhibition rate is less than 90% to 70% or more 3 Mycelial elongation inhibition rate is less than 70% to 40% or more Inhibition of hyphal elongation Those whose rate is % or more are less than 40% to 20 Those whose hyphal elongation inhibition rate is less than 20%
添付した図面は本発明に係る表１の化合物番号１〜６の
化合物の赤外吸収スペクトルを示す。
第１図は化合物番号１、第２図は化合物番号２、第３図
は化合物番号３、第４図は化合物番号４、第５図は化合
物番号５、第６図は化合物番号６の化合物の赤外吸収ス
ペクトルを示す。The attached drawings show infrared absorption spectra of compounds numbered 1 to 6 in Table 1 according to the present invention. Figure 1 shows compound number 1, Figure 2 shows compound number 2, Figure 3 shows compound number 3, Figure 4 shows compound number 4, Figure 5 shows compound number 5, and Figure 6 shows compound number 6. Infrared absorption spectrum is shown.
Claims (3)
、フェニル基を表わす。またＲはＣ＿１〜Ｃ＿３のアル
キル基を表わす） で示されるアシル化トリアゾール誘導体。(1) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, An acylated triazole derivative represented by (representing a group).
、フェニル基を表わす。） で示されるトリアゾール誘導体を触媒の存在下に一般式
（III） Ｒ−ＣＯ−Ｏ−ＣＯ−Ｒ（III） （式中、ＲはＣ＿１〜＿３のアルキル基を表わす）で示
される酸無水物と反応させることを特徴とする 一般式（ I ） ▲数式、化学式、表等があります▼（ I ） （式中、Ｘはハロゲン原子、Ｃ＿１〜＿４のアルキル基
、フェニル基を表わす。またＲはＣ＿１〜＿３のアルキ
ル基を表わす。） で示されるアシル化トリアゾール誘導体の製造法。(2) General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (In the formula, X represents a halogen atom, an alkyl group of C_1 to_4, or a phenyl group.) Catalyst the triazole derivative represented by is characterized by reacting with an acid anhydride represented by the general formula (III) R-CO-O-CO-R(III) (wherein R represents an alkyl group of C_1 to_3) in the presence of General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, .) A method for producing an acylated triazole derivative.
、フェニル基を表わす。またＲはＣ＿１〜＿３のアルキ
ル基を表わす。） で示されるアシル化トリアゾール誘導体を活性成分とし
て含有する農園芸用殺菌剤。(3) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, An agricultural and horticultural fungicide containing an acylated triazole derivative represented by the following formula (representing a group) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25305588A JP2723554B2 (en) | 1988-10-07 | 1988-10-07 | Novel acylated triazole derivative, process for producing the same and agricultural / horticultural fungicide containing the derivative as an active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25305588A JP2723554B2 (en) | 1988-10-07 | 1988-10-07 | Novel acylated triazole derivative, process for producing the same and agricultural / horticultural fungicide containing the derivative as an active ingredient |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02101067A true JPH02101067A (en) | 1990-04-12 |
| JP2723554B2 JP2723554B2 (en) | 1998-03-09 |
Family
ID=17245856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25305588A Expired - Lifetime JP2723554B2 (en) | 1988-10-07 | 1988-10-07 | Novel acylated triazole derivative, process for producing the same and agricultural / horticultural fungicide containing the derivative as an active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2723554B2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0488395A1 (en) * | 1990-11-30 | 1992-06-03 | Kureha Kagaku Kogyo Kabushiki Kaisha | Optically active triazole derivatives and agricultural and horticultural compositions |
| WO2014167008A1 (en) | 2013-04-12 | 2014-10-16 | Bayer Cropscience Ag | Novel triazolinthione derivatives |
| WO2014167009A1 (en) | 2013-04-12 | 2014-10-16 | Bayer Cropscience Ag | Novel triazole derivatives |
| WO2016050769A1 (en) | 2014-10-02 | 2016-04-07 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives useful as fungicides |
| WO2016156282A1 (en) | 2015-04-02 | 2016-10-06 | Bayer Cropscience Aktiengesellschaft | Novel triazole compounds for controlling phytopathogenic harmful fungi |
| WO2016156290A1 (en) | 2015-04-02 | 2016-10-06 | Bayer Cropscience Aktiengesellschaft | Novel 5-substituted imidazole derivatives |
| WO2016156294A1 (en) | 2015-04-02 | 2016-10-06 | Bayer Cropscience Aktiengesellschaft | Triazol derivatives as fungicides |
| WO2018050456A1 (en) | 2016-09-13 | 2018-03-22 | Bayer Cropscience Aktiengesellschaft | Active compound combinations comprising a 5-substituted imidazole derivative |
| WO2018050535A1 (en) | 2016-09-13 | 2018-03-22 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| WO2018060074A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel 5-substituted imidazolylmethyl derivatives |
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| WO2018060076A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
| WO2018060091A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel 5-substituted imidazolylmethyl derivatives |
| WO2018060093A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | 1,5-substituted imidazole derivatives as fungicides for crop protection. |
| WO2018060070A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
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| WO2019091898A1 (en) | 2017-11-09 | 2019-05-16 | Bayer Aktiengesellschaft | Process for the preparation of 5-substituted imidazole derivatives and manganese compounds useful therefor |
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-
1988
- 1988-10-07 JP JP25305588A patent/JP2723554B2/en not_active Expired - Lifetime
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0488395A1 (en) * | 1990-11-30 | 1992-06-03 | Kureha Kagaku Kogyo Kabushiki Kaisha | Optically active triazole derivatives and agricultural and horticultural compositions |
| WO2014167008A1 (en) | 2013-04-12 | 2014-10-16 | Bayer Cropscience Ag | Novel triazolinthione derivatives |
| WO2014167009A1 (en) | 2013-04-12 | 2014-10-16 | Bayer Cropscience Ag | Novel triazole derivatives |
| WO2016050769A1 (en) | 2014-10-02 | 2016-04-07 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives useful as fungicides |
| WO2016156282A1 (en) | 2015-04-02 | 2016-10-06 | Bayer Cropscience Aktiengesellschaft | Novel triazole compounds for controlling phytopathogenic harmful fungi |
| WO2016156290A1 (en) | 2015-04-02 | 2016-10-06 | Bayer Cropscience Aktiengesellschaft | Novel 5-substituted imidazole derivatives |
| WO2016156294A1 (en) | 2015-04-02 | 2016-10-06 | Bayer Cropscience Aktiengesellschaft | Triazol derivatives as fungicides |
| WO2018050456A1 (en) | 2016-09-13 | 2018-03-22 | Bayer Cropscience Aktiengesellschaft | Active compound combinations comprising a 5-substituted imidazole derivative |
| WO2018050535A1 (en) | 2016-09-13 | 2018-03-22 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| WO2018060074A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel 5-substituted imidazolylmethyl derivatives |
| WO2018060075A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | 1 -[2-(1 -chlorocyclopropyl)-2-hydroxy-3-(3-phenyl-1,2-oxazol-5-yl)propyl]-1h-imidazole-5-carbonitrile derivatives and related compounds as fungicides for crop protection |
| WO2018060071A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
| WO2018060076A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
| WO2018060091A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel 5-substituted imidazolylmethyl derivatives |
| WO2018060093A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | 1,5-substituted imidazole derivatives as fungicides for crop protection. |
| WO2018060070A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
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| WO2019091898A1 (en) | 2017-11-09 | 2019-05-16 | Bayer Aktiengesellschaft | Process for the preparation of 5-substituted imidazole derivatives and manganese compounds useful therefor |
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| Publication number | Publication date |
|---|---|
| JP2723554B2 (en) | 1998-03-09 |
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