JPH0226632B2 - - Google Patents
Info
- Publication number
- JPH0226632B2 JPH0226632B2 JP56159083A JP15908381A JPH0226632B2 JP H0226632 B2 JPH0226632 B2 JP H0226632B2 JP 56159083 A JP56159083 A JP 56159083A JP 15908381 A JP15908381 A JP 15908381A JP H0226632 B2 JPH0226632 B2 JP H0226632B2
- Authority
- JP
- Japan
- Prior art keywords
- powdery mildew
- trichloroethyl
- compound
- triazole
- water
- 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.)
- Expired - Lifetime
Links
- -1 2,6- Difluorophenyl Chemical group 0.000 claims description 33
- 241000221785 Erysiphales Species 0.000 claims description 18
- 150000001408 amides Chemical class 0.000 claims description 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 19
- 239000000203 mixture Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 230000000855 fungicidal effect Effects 0.000 description 7
- 239000000417 fungicide Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 150000003852 triazoles Chemical group 0.000 description 5
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000000887 hydrating effect Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000220225 Malus Species 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- KGHXFBVYXDFJGG-UHFFFAOYSA-N (2-carbamoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(N)=O KGHXFBVYXDFJGG-UHFFFAOYSA-N 0.000 description 1
- AVRQBXVUUXHRMY-UHFFFAOYSA-N 2,6-difluorobenzamide Chemical compound NC(=O)C1=C(F)C=CC=C1F AVRQBXVUUXHRMY-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- HXHSJJSCCOVDKR-UHFFFAOYSA-N N-[2,2,2-trichloro-1-(1H-imidazol-2-yl)ethyl]formamide Chemical class N1C(=NC=C1)C(C(Cl)(Cl)Cl)NC=O HXHSJJSCCOVDKR-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
本発明の下記一般式〔〕で表わされるＮ―
〔１―トリアゾール―(1)―イル―２，２，２―ト
リクロロエチル〕―置換アミド誘導体及び該誘導
体を含有するうどんこ病防除剤に関する。
（式中、Ｒは２―フルオロフエニル，２，６―
ジフルオロフエニル，２―トリフルオロメチルフ
エニル，２―ヨードフエニル，２―ヒドロキシフ
エニル，２―アセトキシフエニル，４―イソプロ
ピルフエニル，４―tert―ブチルフエニル，２―
クロロ―４―ニトロフエニル又はベンジル基を表
わす。）
従来、トリアゾール基を有する植物病害防除剤
は多数知られており、例えば特開昭52−148073号
公報，特開昭55−17390号公報などがある。
またＮ―（アゾリルハロゲノアルキル）―カル
ボキサミド誘導体も若干は知られている。例えば
Ｎ―（１―イミダゾリル―２，２，２―トリクロ
ロエチル）―カルボキサミド誘導体が抗真菌作用
を有する事が知られているけれども〔Chem，
Abst.83 114405e（1975）〕農園芸用殺菌剤として
の作用については全くふれられていない。
またＮ―〔１―アゾリル―２，２，３―トリク
ロロプロピル）―カルボキサミド誘導体に殺菌作
用のある事も知られている〔Chem，Abst.87
152221ｇ（1977），特開昭52−17473号公報〕。し
かし、その明細書中に農園芸用殺菌剤としての生
物試験例は記載されていない。
本発明者等は新しい農園芸用殺菌剤の開発を目
標に新規なＮ―〔１―トリアゾール―(1)―イル―
２，２，２―トリクロロエチル〕―置換アミド誘
導体を合成し、広くスクリーニングした結果、前
記一般式〔〕で表わされる化合物が特異的に穀
物，野菜，果樹，花卉等のうどんこ病に優れた殺
菌作用を有する事を見出し本発明をなすに至つ
た。
本発明の化合物は強い浸透作用を有すると共
に、予防，治療効果にも優れ、病害を直接的また
は浸透的に防除する事が出来る。この前記化合物
の植物組織内へ良く浸透する性質が作物の病害防
除面に数多くの利点をもたらす。例えば植物体内
部に侵入した病原菌や種子伝染性の病原菌をこの
ような浸透性を持つた殺菌剤を用いる事によつて
効率良く防除出来る。また殺菌剤を作物の茎葉に
散布し、薬剤が植物体表面に不均一に付着した場
合でも浸透性を持つた殺菌剤であれば病害を適確
に防除出来る。
この事は薬剤施用方法において、茎葉処理に加
えて、土壌処理あるいは種子処理を可能にし、薬
剤施用の省力化をもたらすものである。
更に本発明の化合物は人畜，魚類に対して高い
安全性を有し、かつ農業上有用な作物に対して実
際の使用上何ら害を及ぼすことなく使用出来る。
本発明の目的は新規なＮ―〔１―トリアゾール
―(1)―イル―２，２，２―トリクロロエチル〕―
置換アミド誘導体及び浸透作用の優れたうどんこ
病防除剤を提供する事にある。
本発明は一般式
（式中、Ｒは２―フルオロフエニル，２，６―
ジフルオロフエニル，２―トリフルオロメチルフ
エニル，２―ヨードフエニル，２―ヒドロキシフ
エニル，２―アセトキシフエニル，４―イソプロ
ピルフエニル，４―tert―ブチルフエニル，２―
クロロ―４―ニトロフエニル又はベンジル基を表
わす）
で表わされるＮ―〔１―トリアゾール―(1)―イル
―２，２，２―トリクロロエチル〕―置換アミド
誘導体及び前記誘導体を含有するうどんこ病防除
剤に係る。
本発明でうどんこ病防除剤の有効成分として用
い得るＮ―〔１―トリアゾール―(1)―イル―２，
２，２―トリクロロエチル〕―置換アミド誘導体
を例示すれば第１表の通りである。
N- represented by the following general formula [] of the present invention
The present invention relates to a [1-triazol-(1)-yl-2,2,2-trichloroethyl]-substituted amide derivative and a powdery mildew control agent containing the derivative. (In the formula, R is 2-fluorophenyl, 2,6-
Difluorophenyl, 2-trifluoromethylphenyl, 2-iodophenyl, 2-hydroxyphenyl, 2-acetoxyphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2-
Represents chloro-4-nitrophenyl or benzyl group. Conventionally, many plant disease control agents having a triazole group have been known, such as JP-A-52-148073 and JP-A-55-17390. Some N-(azolylhalogenoalkyl)-carboxamide derivatives are also known. For example, although N-(1-imidazolyl-2,2,2-trichloroethyl)-carboxamide derivatives are known to have antifungal activity [Chem,
Abst. 83 114405e (1975)] There is no mention of its action as an agricultural or horticultural fungicide. It is also known that N-[1-azolyl-2,2,3-trichloropropyl)-carboxamide derivatives have bactericidal activity [Chem, Abst. 87
152221g (1977), Japanese Unexamined Patent Publication No. 17473/1983]. However, the specification does not describe any biological test examples as a fungicide for agriculture and horticulture. The present inventors aimed to develop a new agricultural and horticultural fungicide using a novel N-[1-triazole-(1)-yl-
As a result of synthesizing and extensively screening 2,2,2-trichloroethyl]-substituted amide derivatives, the compound represented by the general formula [] was found to be specifically effective against powdery mildew on cereals, vegetables, fruit trees, flowers, etc. It was discovered that it has a bactericidal effect, leading to the present invention. The compound of the present invention has a strong penetrating action and is also excellent in preventive and therapeutic effects, and can control diseases directly or penetratively. The property of these compounds to penetrate well into plant tissue provides numerous advantages in terms of crop disease control. For example, pathogenic bacteria that have invaded the inside of a plant or seed-borne pathogens can be efficiently controlled by using a fungicide that has such permeability. Furthermore, even if a fungicide is sprayed on the leaves of a crop and the fungicide adheres unevenly to the surface of the plant, it is possible to accurately control diseases if the fungicide is permeable. This enables soil treatment or seed treatment in addition to foliage treatment in the chemical application method, resulting in labor savings in chemical application. Furthermore, the compounds of the present invention are highly safe for humans, livestock, and fish, and can be used without causing any harm to agriculturally useful crops. The object of the present invention is to develop novel N-[1-triazol-(1)-yl-2,2,2-trichloroethyl]-
The object of the present invention is to provide a substituted amide derivative and a powdery mildew control agent with excellent penetration action. The present invention is based on the general formula (In the formula, R is 2-fluorophenyl, 2,6-
Difluorophenyl, 2-trifluoromethylphenyl, 2-iodophenyl, 2-hydroxyphenyl, 2-acetoxyphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2-
N-[1-triazol-(1)-yl-2,2,2-trichloroethyl]-substituted amide derivative represented by chloro-4-nitrophenyl or benzyl group) and powdery mildew control containing said derivative Related to drugs. N-[1-triazol-(1)-yl-2, which can be used as an active ingredient of powdery mildew control agent in the present invention,
Examples of 2,2-trichloroethyl]-substituted amide derivatives are shown in Table 1.
【表】【table】
【表】【table】
【表】
本発明に使用する有効成分化合物は大略次のよ
うにして合成する事ができる。
（式中、Ｒは２―フルオロフエニル，２，６―
ジフルオロフエニル，２―トリフルオロメチルフ
エニル，２―ヨードフエニル，２―ヒドロキシフ
エニル，２―アセトキシフエニル，４―イソプロ
ピルフエニル，４―tert―ブチルフエニル，２―
クロロ―４―ニトロフエニル又はベンジル基を表
わす。）
すなわちＮ―（１，２，２，２―テトラクロロ
エチル）―置換アミドをベンゼンまたはアセトニ
トリル等の有機溶媒中に懸濁または溶解し、これ
に等モルからやや過剰モルの１，２，４―トリア
ゾールを加え更に等モルのトリエチルアミンを加
えて、氷水冷却下から室温で１〜８時間撹拌する
事により目的のＮ―〔１―トリアゾール―(1)―イ
ル―２，２，２―トリクロロエチル〕―置換アミ
ド誘導体を得る事が出来る。
次に実施例により本発明を具体的に説明する。
実施例 １
Ｎ―〔１―（１，２，４―トリアゾール―１―
イル）―２，２，２―トリクロロエチル〕―
２，６―ジフルオロベンズアミド（化合物番号
２）の合成
Ｎ―（１，２，２，２―テトラクロロエチル）
―２，６―ジフルオロベンズアミド4.8ｇ（0.015
モル）をアセトニトリル50mlに懸濁し、氷水冷却
下、１，２，４―トリアゾール1.1ｇ（0.015モ
ル）とトリエチルアミン1.5ｇ（0.015モル）をア
セトニトリル20mlに溶解し滴下した。室温にもど
るまで３時間撹拌し析出した白色結晶と共に水中
に投入した。
析出する白色結晶を別乾燥後少量のアセトニ
トリルから再結晶して融点170―172℃の化合物番
号２の化合物を白色結晶として2.9ｇ（収率55％）
を得た。
該化合物のIR及びNMRによる分析結果を下記
に示す。
IR（KBr，cm-1）；3110（NH），1680（CO）
NMR（d6―DMSO），δ（ppm）；7.0〜7.9（3H，
ｍ，ベンゼン環プロトン），7.42（1H，ｄ，
Ｊ＝10Hz，Ｃ―Ｈ），8.20，9.11（各1H，
ｓ，トリアゾール環プロトン），10.87（1H，
ｄ，Ｊ＝10Hz，NH）
実施例 ２
Ｎ―〔１―（１，２，４―トリアゾール―１―
イル）―２，２，２―トリクロロエチル〕―２
―トリフルオロメチルベンズアミド（化合物番
号３）の合成
Ｎ―（１，２，２，２―テトラクロロエチル）
―２―トリフルオロメチルベンズアミド2.5ｇ
（0.007モル）をアセトニトリル30mlに懸濁し、氷
水冷却下１，２，４―トリアゾール0.53ｇ
（0.0077モル）とトリエチルアミン0.78ｇ（0.0077
モル）をアセトニトリル20mlに溶解し滴下し、室
温にもどるまで４時間撹拌した。かくして得られ
た反応液を減圧濃縮し白色半固体物質を得た。こ
れを水中で良く粉砕洗浄して白色結晶とした。少
量のアセトニトリルから再結晶して融点153〜156
℃の化合物番号３の化合物を白色結晶として1.7
ｇ（収率63％）を得た。該化合物のIR及びNMR
による分析結果を下記に示す。
IR（KBr，cm-1）；3130（NH），1660（CO）
NMR（d6―DMSO），δ（ppm）：7.4（1H，ｄ，
Ｊ＝10Hz，Ｃ―Ｈ），7.58〜7.98（4H，ｍ，
ベンゼン環プロトン），8.2，9.1（各1H，ｓ，
トリアゾール環プロトン），10.7（1H，ｄ，
Ｊ＝10Hz，NH）
実施例 ３
Ｎ―〔１―（１，２，４―トリアゾール―１―
イル）―２，２，２―トリクロロエチル〕―２
―アセトキシベンズアミド（化合物番号６）の
合成
Ｎ―（１，２，２，２―テトラクロロエチル）
―２―アセトキシベンズアミド5.2ｇ（0.015モ
ル）をアセトニトリル70mlに懸濁し氷水冷却下
１，２，４―トリアゾール1.1ｇ（0.015モル）と
トリエチルアミン1.5ｇ（0.015モル）をアセトニ
トリル20mlに溶解し滴下した。冷却下１時間撹拌
し、析出した白色結晶と共に水中に投入した。析
出する白色結晶を別、良く水洗し融点154―156
℃の化合物番号６の化合物を白色結晶として5.3
ｇ（収率95％）を得た。
該化合物のIR及びNMRによる分析結果を下記
に示す。
IR（KBr，cm-1）；3410（NH），1780（OCO），
1665（CO）
NMR（d6―DMSO），δ（ppm）；2.23（3H，ｓ，
COCH3），7.28〜7.91（5H，ｍ，ベンゼン環
プロトン＋Ｃ―Ｈ），8.32，9.29（各1H，
ｓ，トリアゾール環プロトン），10.25（1H，
ｄ，Ｊ＝10Hz，NH）
本発明化合物の有効性を証するための若干の実
施例を示す。
本発明のうどんこ病防除剤は例えば下記処方１
及び処方２に従がつて調整される。
処方１ 水和剤
（重量部）
本発明化合物 化合物番号２ 50部
リグニンスルホン酸塩 ５部
アルキルスルホン酸塩 ３部
珪藻土 42部
上記各成分を混合粉砕し水和剤とし、水で希釈
して使用する。（ここで希釈剤及び助剤の種類、
その混合比及び有効成分量は広い範囲で変更し得
る。）
処方２ 粒剤
（重量部）
本発明化合物 化合物番号３ ８部
ベントナイト 40部
クレー 45部
リグニンスルホン酸塩 ７部
上記各成分を均一に混合し、更に水を加えて練
合せ、押出式造粒機で粒状に加工乾燥して粒剤と
する。（ここで担体及び助剤の種類その混合比及
び有効成分量は広い範囲で変更し得る。）
実施例 ４
小麦うどんこ病防除効果試験
径10cmの素焼鉢を用いて栽培した第３本葉時の
幼苗小麦（品種：農林64号、16本／鉢）に処方１
の如き水和剤を所定濃度に水で希釈懸濁し散布し
た。散布葉乾燥後に罹病葉から採取したうどんこ
病菌の胞子懸濁液を噴霧接種し、ガラス温室内に
放置した。10日後に次の調査基準により罹病度を
調査した。結果を第２表に示す。[Table] The active ingredient compound used in the present invention can be synthesized roughly as follows. (In the formula, R is 2-fluorophenyl, 2,6-
Difluorophenyl, 2-trifluoromethylphenyl, 2-iodophenyl, 2-hydroxyphenyl, 2-acetoxyphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2-
Represents chloro-4-nitrophenyl or benzyl group. ) That is, N-(1,2,2,2-tetrachloroethyl)-substituted amide is suspended or dissolved in an organic solvent such as benzene or acetonitrile, and an equimolar to slightly excess molar amount of 1,2,4- Add triazole, further add equimolar amount of triethylamine, and stir at room temperature for 1 to 8 hours while cooling with ice water to obtain the desired N-[1-triazol-(1)-yl-2,2,2-trichloroethyl]. -Substituted amide derivatives can be obtained. Next, the present invention will be specifically explained with reference to Examples. Example 1 N-[1-(1,2,4-triazole-1-
yl)-2,2,2-trichloroethyl]-
Synthesis of 2,6-difluorobenzamide (compound number 2) N-(1,2,2,2-tetrachloroethyl)
-2,6-difluorobenzamide 4.8g (0.015
1.1 g (0.015 mol) of 1,2,4-triazole and 1.5 g (0.015 mol) of triethylamine dissolved in 20 ml of acetonitrile were added dropwise under cooling with ice water. The mixture was stirred for 3 hours until the temperature returned to room temperature, and the mixture was poured into water together with precipitated white crystals. The precipitated white crystals were dried separately and then recrystallized from a small amount of acetonitrile to obtain 2.9 g of compound No. 2 with a melting point of 170-172°C as white crystals (yield 55%).
I got it. The analysis results of this compound by IR and NMR are shown below. IR (KBr, cm -1 ); 3110 (NH), 1680 (CO) NMR (d 6 -DMSO), δ (ppm); 7.0-7.9 (3H,
m, benzene ring proton), 7.42 (1H, d,
J=10Hz, C-H), 8.20, 9.11 (1H each,
s, triazole ring proton), 10.87 (1H,
d, J=10Hz, NH) Example 2 N-[1-(1,2,4-triazole-1-
yl)-2,2,2-trichloroethyl]-2
-Synthesis of trifluoromethylbenzamide (compound number 3) N-(1,2,2,2-tetrachloroethyl)
-2-trifluoromethylbenzamide 2.5g
(0.007 mol) was suspended in 30 ml of acetonitrile, and 0.53 g of 1,2,4-triazole was cooled with ice water.
(0.0077 mol) and triethylamine 0.78 g (0.0077
mol) was dissolved in 20 ml of acetonitrile and added dropwise, and the mixture was stirred for 4 hours until the temperature returned to room temperature. The reaction solution thus obtained was concentrated under reduced pressure to obtain a white semi-solid substance. This was thoroughly crushed and washed in water to obtain white crystals. Recrystallized from a small amount of acetonitrile, melting point 153-156
1.7 as white crystals of compound number 3 at ℃
g (63% yield) was obtained. IR and NMR of the compound
The analysis results are shown below. IR (KBr, cm -1 ); 3130 (NH), 1660 (CO) NMR (d 6 -DMSO), δ (ppm): 7.4 (1H, d,
J=10Hz, C-H), 7.58-7.98 (4H, m,
benzene ring proton), 8.2, 9.1 (each 1H, s,
triazole ring proton), 10.7 (1H, d,
J=10Hz, NH) Example 3 N-[1-(1,2,4-triazole-1-
yl)-2,2,2-trichloroethyl]-2
-Synthesis of acetoxybenzamide (compound number 6) N-(1,2,2,2-tetrachloroethyl)
5.2 g (0.015 mol) of -2-acetoxybenzamide was suspended in 70 ml of acetonitrile, and 1.1 g (0.015 mol) of 1,2,4-triazole and 1.5 g (0.015 mol) of triethylamine dissolved in 20 ml of acetonitrile were added dropwise while cooling with ice water. The mixture was stirred for 1 hour under cooling and poured into water together with precipitated white crystals. Separate the precipitated white crystals and wash thoroughly with water, melting point 154-156.
Compound No. 6 at ℃ as white crystals 5.3
g (yield 95%) was obtained. The analysis results of this compound by IR and NMR are shown below. IR (KBr, cm -1 ); 3410 (NH), 1780 (OCO),
1665 (CO) NMR (d 6 -DMSO), δ (ppm); 2.23 (3H, s,
COCH 3 ), 7.28-7.91 (5H, m, benzene ring proton + C-H), 8.32, 9.29 (1H each,
s, triazole ring proton), 10.25 (1H,
d, J=10Hz, NH) Some examples are shown to demonstrate the effectiveness of the compounds of the present invention. The powdery mildew control agent of the present invention is, for example, the following formulation 1.
and adjusted according to Formulation 2. Formulation 1 Wettable powder (parts by weight) Compound of the present invention Compound No. 2 50 parts Lignosulfonate 5 parts Alkyl sulfonate 3 parts Diatomaceous earth 42 parts Mix and grind the above ingredients to make a wettable powder, dilute with water and use. do. (Here, the type of diluent and auxiliary agent,
The mixing ratio and the amount of active ingredient can vary within a wide range. ) Formulation 2 Granules (parts by weight) Compound of the present invention Compound No. 3 8 parts Bentonite 40 parts Clay 45 parts Lignosulfonate 7 parts The above components were mixed uniformly, water was added and kneaded, and extrusion granulation was performed. It is machined into granules and dried to make granules. (Here, the types, mixing ratios, and amounts of active ingredients of carriers and auxiliary agents can be varied within a wide range.) Example 4 Wheat powdery mildew control efficacy test At the third true leaf stage grown using clay pots with a diameter of 10 cm Prescription 1 for young wheat seedlings (variety: Norin No. 64, 16 plants/pot)
A wettable powder such as the following was diluted and suspended in water to a predetermined concentration and then sprayed. After drying the sprayed leaves, a spore suspension of powdery mildew collected from the diseased leaves was spray inoculated and left in a glass greenhouse. After 10 days, the degree of morbidity was investigated according to the following investigation criteria. The results are shown in Table 2.
【表】【table】
【表】
実施例 ５
小麦うどんこ病防除効果試験（種子処理試験）
小麦種子（品種：農林64号）30粒を処方１の如
き水和剤の所定濃度に水で希釈懸濁せしめた液に
３時間浸漬し、径10cmの素焼鉢に播種した。第２
本葉時（播種10日後）に罹病葉から採取したうど
んこ病菌の胞子懸濁液を噴霧接種し、10日後に実
施例４の如き調査基準にて罹病度を調査した。結
果を第３表に示す。[Table] Example 5 Wheat powdery mildew control effect test (seed treatment test) 30 grains of wheat seeds (variety: Norin No. 64) were diluted and suspended in water to a predetermined concentration of a hydrating powder such as Formulation 1. After soaking for 3 hours, the seeds were sown in clay pots with a diameter of 10 cm. Second
At the time of true leaves (10 days after sowing), a spore suspension of powdery mildew collected from diseased leaves was inoculated by spraying, and 10 days later, the disease severity was investigated using the investigation criteria as in Example 4. The results are shown in Table 3.
【表】
実施例 ６
トマトうどんこ病防除効果試験
径10cmの素焼鉢を用いて栽培した第５本葉時の
トマト（品種：福寿２号、１本／鉢、３鉢／処理
区使用）に処方１の如き水和剤を所定濃度に水で
希釈懸濁し散布した。散布葉風乾後、罹病葉より
採取したうどんこ病菌の胞子懸濁液を噴霧接種
し、10日後に実施例４の如き調査基準にて罹病度
を調査した。結果を第４表に示す。[Table] Example 6 Tomato powdery mildew control effect test Tomatoes at the fifth true leaf stage (cultivar: Fukuju No. 2, 1 plant/pot, 3 pots/treated area used) grown using clay pots with a diameter of 10 cm A hydrating powder such as Formulation 1 was diluted and suspended in water to a predetermined concentration and then sprayed. After the sprayed leaves were air-dried, a spore suspension of powdery mildew collected from the diseased leaves was spray inoculated, and 10 days later, the disease severity was investigated using the same investigation criteria as in Example 4. The results are shown in Table 4.
【表】
実施例 ７
リンゴうどんこ病防除効果試験
リンゴの実生苗に処方１の如き水和剤を所定濃
度に水で希釈懸濁し散布し、ビニールハウス内に
放置しリンゴうどんこ病の自然発生を促した。散
布処理14日後に発病度を下記の方法により調査し
算出した。即ち、調査葉の病斑出現度に応じて
０，0.5，１，２，４の指数に分類し、次式によ
り発病度を算出した。結果を第５表に示す。[Table] Example 7 Apple powdery mildew control effect test A hydrating powder such as Formulation 1 was diluted and suspended in water to a predetermined concentration and sprayed on apple seedlings, and left in a plastic greenhouse to evaluate the natural occurrence of apple powdery mildew. urged. Fourteen days after the spraying treatment, the severity of disease was investigated and calculated using the following method. That is, the lesions were classified into indexes of 0, 0.5, 1, 2, and 4 according to the degree of appearance of lesions on the examined leaves, and the degree of disease severity was calculated using the following formula. The results are shown in Table 5.
【表】
調査葉数×４
[Table] Number of leaves examined x 4
【表】
実施例 ８
バラうどんこ病防除効果試験
バラ（品種：ビース）を径30cmの素焼鉢で裁培
し、うどんこ病が自然発生し始めた頃、処方１の
如き水和剤を水で希釈懸濁し、散布した。風乾後
ビニールハウス内に放置し、うどんこ病の発生を
促した。散布処理10日後に実施例７の如き調査基
準にて発病度を調査した。結果を第６表に示す。[Table] Example 8 Rose powdery mildew control effect test Roses (variety: Bees) were cultivated in clay pots with a diameter of 30 cm, and when powdery mildew began to appear naturally, a hydrating powder such as formulation 1 was added to the water. The solution was diluted and suspended in water and sprayed. After air-drying, they were left in a plastic greenhouse to encourage the development of powdery mildew. Ten days after the spraying treatment, the disease severity was investigated using the same investigation criteria as in Example 7. The results are shown in Table 6.
【表】【table】
Claims (1)
ジフルオロフエニル，２―トリフルオロメチルフ
エニル，２―ヨードフエニル，２―ヒドロキシフ
エニル，２―アセトキシフエニル，４―イソプロ
ピルフエニル，４―tert―ブチルフエニル，２―
クロロ―４―ニトロフエニル又はベンジル基を表
す） で示されるＮ―〔１―トリアゾール―(1)―イル―
２，２，２―トリクロロエチル〕―置換アミド誘
導体。 ２ 一般式 （式中、Ｒは２―フルオロフエニル，２，６―
ジフルオロフエニル，２―トリフルオロメチルフ
エニル，２―ヨードフエニル，２―ヒドロキシフ
エニル、２―アセトキシフエニル，４―イソプロ
ピルフエニル，４―tert―ブチルフエニル，２―
クロロ―４―ニトロフエニル又はベンジル基を表
す） で示されるＮ―〔１―トリアゾール―(1)―イル―
２，２，２―トリクロロエチル〕―置換アミド誘
導体を含有するうどんこ病防除剤。[Claims] 1. General formula (In the formula, R is 2-fluorophenyl, 2,6-
Difluorophenyl, 2-trifluoromethylphenyl, 2-iodophenyl, 2-hydroxyphenyl, 2-acetoxyphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2-
chloro-4-nitrophenyl or benzyl group) N-[1-triazol-(1)-yl-
2,2,2-trichloroethyl]-substituted amide derivative. 2 General formula (In the formula, R is 2-fluorophenyl, 2,6-
Difluorophenyl, 2-trifluoromethylphenyl, 2-iodophenyl, 2-hydroxyphenyl, 2-acetoxyphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2-
chloro-4-nitrophenyl or benzyl group) N-[1-triazol-(1)-yl-
A powdery mildew control agent containing a 2,2,2-trichloroethyl]-substituted amide derivative.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56159083A JPS5859975A (en) | 1981-10-06 | 1981-10-06 | N-(1-triazol-(1)-yl-2,2,2-trichloroethyl)-substituted amide derivative and controlling agent against powdery mildew containing said derivative |
| DK179182A DK179182A (en) | 1981-10-06 | 1982-04-22 | N- (1-TRIAZOL- (1) -YL-2,2,2-TRICHLORETHYL) -SUBSTITUTED CARBOXAMIDE DERIVATIVE AND POWDER-SHAPED MILK DEVICES CONTAINING THIS AS ACTIVE INGREDIENT |
| GB08212326A GB2106895B (en) | 1981-10-06 | 1982-04-28 | N-(1-triazol-(1)-yl-2-2-2-trichloroethyl)-substituted carboxamides for controlling mildew |
| DE19823215771 DE3215771A1 (en) | 1981-10-06 | 1982-04-28 | N- (1-TRIAZOLE- (1) -YL-2,2,2-TRICHLORETHYL) -CARBOXAMIDE DERIVATIVES AND COMPOSITIONS CONTAINING THESE DERIVATIVES FOR CONTROLLING MEWN |
| NL8201794A NL8201794A (en) | 1981-10-06 | 1982-04-29 | DERIVATIVE OF N-1-TRIAZOL- (1) -YL-2,2,2-TRICHLOROETHYL-SUBSTITUTED CARBOXAMIDE AND AN AGENT FOR THE PREPARATION OF POWDER MILK, AS AN ACTIVE SUBSTANCE. |
| FR8207493A FR2513997A1 (en) | 1981-10-06 | 1982-04-30 | SUBSTITUTED N- (1-TRIAZOLE- (1) -YL-2,2,2-TRICHLORETHYL) -CARBOXAMIDE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND OIDIUM COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENTS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56159083A JPS5859975A (en) | 1981-10-06 | 1981-10-06 | N-(1-triazol-(1)-yl-2,2,2-trichloroethyl)-substituted amide derivative and controlling agent against powdery mildew containing said derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5859975A JPS5859975A (en) | 1983-04-09 |
| JPH0226632B2 true JPH0226632B2 (en) | 1990-06-12 |
Family
ID=15685850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56159083A Granted JPS5859975A (en) | 1981-10-06 | 1981-10-06 | N-(1-triazol-(1)-yl-2,2,2-trichloroethyl)-substituted amide derivative and controlling agent against powdery mildew containing said derivative |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5859975A (en) |
| DE (1) | DE3215771A1 (en) |
| DK (1) | DK179182A (en) |
| FR (1) | FR2513997A1 (en) |
| GB (1) | GB2106895B (en) |
| NL (1) | NL8201794A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05179881A (en) * | 1991-12-27 | 1993-07-20 | Dia Consultant:Kk | Continuous penetration testing method of ground and device therefor |
| CN105541828A (en) * | 2014-12-10 | 2016-05-04 | 沈阳药科大学 | Acylaminoimidazole derivative and use thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2650840B2 (en) * | 1993-12-03 | 1997-09-10 | 和泉オプトパーツ株式会社 | Security light |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5777678A (en) * | 1980-10-31 | 1982-05-15 | Kureha Chem Ind Co Ltd | N-(1-triazol-(1)-yl-2,2,2-trichloroethyl)-substituted benzamide derivative and agent for controlling powdery mildew containing said derivative |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE756062A (en) * | 1969-09-11 | 1971-03-11 | Boehringer Sohn Ingelheim | 1,1,1-TRICHLORETHANE DERIVATIVES THEIR MANUFACTURING PROCESSES AND THEIR USE AS BIOCIDAL SUBSTANCES |
-
1981
- 1981-10-06 JP JP56159083A patent/JPS5859975A/en active Granted
-
1982
- 1982-04-22 DK DK179182A patent/DK179182A/en not_active Application Discontinuation
- 1982-04-28 GB GB08212326A patent/GB2106895B/en not_active Expired
- 1982-04-28 DE DE19823215771 patent/DE3215771A1/en not_active Ceased
- 1982-04-29 NL NL8201794A patent/NL8201794A/en not_active Application Discontinuation
- 1982-04-30 FR FR8207493A patent/FR2513997A1/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5777678A (en) * | 1980-10-31 | 1982-05-15 | Kureha Chem Ind Co Ltd | N-(1-triazol-(1)-yl-2,2,2-trichloroethyl)-substituted benzamide derivative and agent for controlling powdery mildew containing said derivative |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05179881A (en) * | 1991-12-27 | 1993-07-20 | Dia Consultant:Kk | Continuous penetration testing method of ground and device therefor |
| CN105541828A (en) * | 2014-12-10 | 2016-05-04 | 沈阳药科大学 | Acylaminoimidazole derivative and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2106895B (en) | 1985-10-23 |
| NL8201794A (en) | 1983-05-02 |
| FR2513997A1 (en) | 1983-04-08 |
| DE3215771A1 (en) | 1983-04-21 |
| DK179182A (en) | 1983-04-07 |
| GB2106895A (en) | 1983-04-20 |
| JPS5859975A (en) | 1983-04-09 |
| FR2513997B1 (en) | 1984-05-25 |
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