JPS645026B2 - - Google Patents
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- Publication number
- JPS645026B2 JPS645026B2 JP54118158A JP11815879A JPS645026B2 JP S645026 B2 JPS645026 B2 JP S645026B2 JP 54118158 A JP54118158 A JP 54118158A JP 11815879 A JP11815879 A JP 11815879A JP S645026 B2 JPS645026 B2 JP S645026B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- compound
- formula
- trichloropropyl
- present
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 21
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- -1 1-(1-n-butyloxy-3,3,3- Trichloropropyl)benzimidazole Chemical compound 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UPTGDTIXYFULAB-UHFFFAOYSA-N 1-(1,3,3,3-tetrachloropropoxy)butane Chemical compound CCCCOC(Cl)CC(Cl)(Cl)Cl UPTGDTIXYFULAB-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】
本発明はトリハロプロパン誘導体に関する。
本発明のトリハロプロパン誘導体は、新規な化
合物であり、下記一般式〔１〕で表わされる。
〔式中R1は低級アルキル基およびＸはハロゲ
ン原子を示す。Ａはメチン（―CH＝）または窒
素原子（―Ｎ＝）を示す。〕
上記一般式〔１〕で表わされる本発明化合物
は、抗菌活性を有し、殊に各種の植物病原性真菌
類に対して優れた殺菌活性を示し、また薬害のお
それもほとんどなく、農園芸用殺菌剤として有用
である。
上記一般式〔１〕において低級アルキル基とし
ては、例えばメチル、エチル、プロピル、イソプ
ロピル、ブチル、tert―ブチル基等を例示でき
る。ハロゲン原子は、弗素、塩素、臭素及び沃素
原子のいずれであつてもよい。また
【式】基としては例えばベンゾイミダ
ゾリル、ベンゾトリアゾリル基等の窒素原子２〜
３個をヘテロ原子として有する５員の不飽和ヘテ
ロ環にベンゼン環が縮合したベンゾヘテロ環を例
示できる。
以下本発明化合物の代表例を示す。
Γ １―（１―ｎ―ブチルオキシ―３，３，３―
トリクロロプロピル）ベンゾイミダゾール
Γ １―（１―エトキシ―３，３，３―トリフプ
ロモプロピル）ベンゾイミダゾール
Γ １―（１―イソプロピルオキシ―３，３，３
―トリクロロプロピル）ベンゾイミダゾール
Γ １―（１―ｎ―ブチルオキシ―３，３，３―
トリクロロプロピル）ベンゾイミダゾール
Γ １―（１―メトキシ―３，３，３―トリクロ
ロプロピル）ベンゾイミダゾール
Γ １―（１―メトキシ―３，３，３―トリクロ
ロプロピル）ベンゾトリアゾール
Γ １―（１―エトキシ―３，３，３―トリクロ
ロプロピル）ベンゾトリアゾール
Γ １―（１―フエノブチルオキシ―３，３，３
―トリクロロプロピル）ベンゾトリアゾール
本発明化合物は、例えば下記一般式
〔式中R1及びＸは上記に同じ〕
で表わされる―アルコキシ―１，１，１，３―テ
トラハロプロパンを原料として、これに適当な不
活性溶媒中、脱酸剤の存在下もしくは不存在下に
一般式
〔式中Ａは上記に同じ〕
で表わされる公知のヘテロ環化合物を反応させる
ことにより製造される。
上記一般式〔２〕で表わされる原料化合物は、
公知化合物であり、例えば次式に示すようにして
合成される〔M.Laevas，Ann.Chem.〔12〕，７，
697（1952）、P.Tarrant，E.C.Stump，J.O.C.29、
1198（1964）、米国特許第2560219号及びC.A.，
46，1023（1952）〕。
〔式中R1及びＸは上記に同じ〕
即ち上記一般式〔４〕で表わされる化合物と一
般式〔５〕で表わされる化合物とを光射照するか
又はラジカル開始剤例えばベンゾイルパーオキサ
イド、アゾビスイソブチロニトリル等の存在下に
50〜100℃の温度下に加熱して反応させることに
より容易に収得できる。
上記一般式〔２〕で表わされる化合物と一般式
〔３〕で表わされる化合物との反応は、より具体
的には次の如くして行なわれる。即ち例えばアセ
トン、メチルエチルケトン等のケトン類、アセト
ニトリル等のニトリル類、ジグライム、テトラヒ
ドロフラン等のエーテル類、四塩化炭素、クロロ
ホルム、塩化メチレン等のハロゲン化炭化水素
類、ベンゼン、トルエン、キシレン等の芳香族炭
化水素類、メタノール、エタノール等のアルコー
ル類、ジメチルスルホキシド等の適当な不活性溶
媒中で、例えば炭酸カリウム、炭酸ナトリウム、
炭酸水素カリウム、炭酸水素ナトリウム、水酸化
カリウム、水酸化ナトリウム、トリエチルアミ
ン、ジメチルアニリン等、好ましくは炭酸カリウ
ム、炭酸ナトリウム、炭酸水素カリウム、炭酸水
素ナトリウム等の弱塩基性化合物を脱酸剤として
利用するか又は用いることなく、一般式〔２〕の
化合物と一般式〔３〕の化合物とを０〜100℃好
ましくは室温〜50℃下に１〜５時間通常１〜２時
間程度反応させることにより行なわれる。一般式
〔２〕の化合物に対する一般式〔３〕の化合物の
使用量は、脱酸剤を用いる場合は、通常等モル以
上好ましくは等モル〜２倍モル程度とし、また脱
酸剤を用いない場合は好ましくは２倍モル以上と
すればよい。また脱酸剤は通常一般式〔２〕の化
合物に対して等モル以上好ましくは等モル〜1.5
倍モル程度用いるのが適当である。
かくして一般式〔１〕で表わされる本発明のト
リハロプロパン誘導体を収得する。得られる化合
物は、反応終了後常法に従いカラムクロマトグラ
フイーや溶媒抽出法、再結晶法等により単離精製
できる。
以下本発明化合物の製造に用いる原料化合物の
製造例を参考例として挙げ、次いで本発明化合物
の製造例を実施例として挙げる。
参考例 １
四塩化炭素150mlにアゾビスイソブチロニトリ
ル300mgを加え還流する。滴下斗よりｎ―ブチ
ルビニルエーテル50ｇを少量づつ滴下し、更に１
時間還流後四塩化炭素を減圧下に除去し、減圧蒸
留する。２mmＨｇ下に74〜75℃の留分として、３
―ｎ―ブチルオキシ―１，１，１，３―テトラク
ロロプロパン118ｇを得る。
実施例 １
３―ｎ―ブチルオキシ―１，１，１，３―テト
ラクロロプロパン5.08ｇをアセトン50mlに溶解
し、室温撹拌下にベンゾイミダゾール2.36ｇを加
え、同温度に更に２時間撹拌を続ける。反応終了
後減圧濃縮し残留物を四塩化炭素200mlに溶解し、
不溶部を除去し、水100mlで洗浄後無水硫酸マグ
ネシウムで乾燥し、四塩化炭素を減圧下に完全に
除去して、淡黄色油状の１―（１―ｎ―ブチルオ
キシ―３，３，３―トリクロロプロピル）ベンゾ
イミダゾール4.5ｇを得る。
屈折率n25 D＝1.5420
NMR（CDCl3）δ；
0.70―1.10（3H，ｍ）1.20―1.70（4H，ｍ）、
3.20―3.80（4H，ｍ）、5.80（1H，ｔ）、7.20―
7.90（3H，ｍ）、8.00（1H，ｓ）、
実施例 ２〜５
上記実施例１と同様にしてR1および
【式】が第１表記載のものである各化
合物を得る。第１表には得られた各化合物の物性
（融点又は屈折率）を併記する。
【式】
【表】
＜抗菌試験＞
本発明化合物（実施例２及び５）の夫々100mg
をアセトン５mlに溶解し、展着剤２滴を加えた水
95mlに混合して、濃度1000ppmの供試液を作成す
る。
各供試液をイネ葉（品種コシヒカリ）に充分に
散布し、散布24時間後に、稲イモチ病菌胞子懸濁
液（100倍で１視野に30個程度）を噴霧接種し、
24時間湿室に保つ。その後25℃で育生し、接種７
日後に最上展開葉の病斑数を調べる。また同様に
して本発明化合物を含有しないアセトン水を徹布
試験した無処理葉の病斑数を計数し、之等の値よ
り防除価（％）を算出した結果は下記第２表の通
りであつた。
【表】 DETAILED DESCRIPTION OF THE INVENTION The present invention relates to trihalopropane derivatives. The trihalopropane derivative of the present invention is a novel compound and is represented by the following general formula [1]. [In the formula, R 1 represents a lower alkyl group and X represents a halogen atom. A represents methine (-CH=) or nitrogen atom (-N=). ] The compound of the present invention represented by the above general formula [1] has antibacterial activity, particularly shows excellent bactericidal activity against various plant pathogenic fungi, and has almost no risk of phytotoxicity, and is useful in agriculture and horticulture. It is useful as a fungicide. Examples of the lower alkyl group in the above general formula [1] include methyl, ethyl, propyl, isopropyl, butyl, and tert-butyl groups. The halogen atom may be any of fluorine, chlorine, bromine, and iodine atoms. In addition, as the group [Formula], for example, 2 to 2 nitrogen atoms such as benzimidazolyl, benzotriazolyl group, etc.
An example is a benzoheterocycle in which a benzene ring is fused to a five-membered unsaturated heterocycle having three heteroatoms. Representative examples of the compounds of the present invention are shown below. Γ 1-(1-n-butyloxy-3,3,3-
Trichloropropyl)benzimidazole Γ 1-(1-ethoxy-3,3,3-trifupromopropyl)benzimidazole Γ 1-(1-isopropyloxy-3,3,3
-trichloropropyl)benzimidazole Γ 1-(1-n-butyloxy-3,3,3-
Trichloropropyl)benzimidazole Γ 1-(1-methoxy-3,3,3-trichloropropyl)benzimidazole Γ 1-(1-methoxy-3,3,3-trichloropropyl)benzotriazole Γ 1-(1-ethoxy -3,3,3-trichloropropyl)benzotriazole Γ 1-(1-phenobutyloxy-3,3,3
-Trichloropropyl)benzotriazole The compound of the present invention can be expressed, for example, by the following general formula: [In the formula, R 1 and General formula in the presence [In the formula, A is the same as above] It is produced by reacting a known heterocyclic compound represented by the following formula. The raw material compound represented by the above general formula [2] is
It is a known compound, and can be synthesized, for example, as shown in the following formula [M.Laevas, Ann.Chem. [12], 7 ,
697 (1952), P. Tarrant, ECStump, JOC 29 ,
1198 (1964), U.S. Patent No. 2,560,219 and CA.
46, 1023 (1952)]. [In the formula, R 1 and In the presence of bisisobutyronitrile etc.
It can be easily obtained by heating and reacting at a temperature of 50 to 100°C. More specifically, the reaction between the compound represented by the above general formula [2] and the compound represented by the general formula [3] is carried out as follows. For example, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile, ethers such as diglyme and tetrahydrofuran, halogenated hydrocarbons such as carbon tetrachloride, chloroform and methylene chloride, and aromatic carbons such as benzene, toluene and xylene. For example, potassium carbonate, sodium carbonate,
Potassium bicarbonate, sodium bicarbonate, potassium hydroxide, sodium hydroxide, triethylamine, dimethylaniline, etc., preferably weakly basic compounds such as potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, etc. are used as deoxidizing agents. The reaction is carried out by reacting the compound of general formula [2] with the compound of general formula [3] at 0 to 100°C, preferably room temperature to 50°C, for 1 to 5 hours, usually for about 1 to 2 hours. It will be done. The amount of the compound of general formula [3] to be used of the compound of general formula [2], when using a deoxidizing agent, is usually equal to or more than the same mole, preferably about 1 to 2 times the mole, and when no deoxidizing agent is used. In this case, it is preferable to increase the amount by 2 times the mole or more. In addition, the deoxidizing agent is usually equal to or more than equimolar, preferably equimolar to 1.5 to the compound of general formula [2].
It is appropriate to use about double the molar amount. In this way, the trihalopropane derivative of the present invention represented by general formula [1] is obtained. After completion of the reaction, the resulting compound can be isolated and purified by column chromatography, solvent extraction, recrystallization, etc. in accordance with conventional methods. Hereinafter, production examples of raw material compounds used for production of the compounds of the present invention will be listed as reference examples, and then production examples of the compounds of the present invention will be listed as examples. Reference Example 1 Add 300 mg of azobisisobutyronitrile to 150 ml of carbon tetrachloride and reflux. Add 50g of n-butyl vinyl ether little by little from the dropping funnel, and add 1
After refluxing for a period of time, carbon tetrachloride is removed under reduced pressure and distilled under reduced pressure. 3 as a fraction of 74-75℃ under 2mmHg
-118 g of n-butyloxy-1,1,1,3-tetrachloropropane is obtained. Example 1 5.08 g of 3-n-butyloxy-1,1,1,3-tetrachloropropane is dissolved in 50 ml of acetone, 2.36 g of benzimidazole is added while stirring at room temperature, and stirring is continued for an additional 2 hours at the same temperature. After the reaction was completed, it was concentrated under reduced pressure and the residue was dissolved in 200ml of carbon tetrachloride.
The insoluble portion was removed, washed with 100 ml of water, dried over anhydrous magnesium sulfate, carbon tetrachloride was completely removed under reduced pressure, and a pale yellow oily 1-(1-n-butyloxy-3,3,3- 4.5 g of benzimidazole (trichloropropyl) are obtained. Refractive index n 25 D = 1.5420 NMR (CDCl 3 ) δ; 0.70-1.10 (3H, m) 1.20-1.70 (4H, m),
3.20―3.80 (4H, m), 5.80 (1H, t), 7.20―
7.90 (3H, m), 8.00 (1H, s), Examples 2 to 5 Compounds in which R 1 and [Formula] are as shown in Table 1 are obtained in the same manner as in Example 1 above. Table 1 also lists the physical properties (melting point or refractive index) of each compound obtained. [Formula] [Table] <Antibacterial test> 100 mg each of the compounds of the present invention (Examples 2 and 5)
Dissolve it in 5 ml of acetone and add 2 drops of a spreading agent to water.
Mix 95ml to create a test solution with a concentration of 1000ppm. Each test solution was sufficiently sprayed on rice leaves (variety Koshihikari), and 24 hours after spraying, a suspension of rice blast fungus spores (approximately 30 per field of view at 100x magnification) was inoculated by spraying.
Keep in a moist room for 24 hours. After that, grow at 25℃ and inoculate 7
After a day, check the number of lesions on the topmost leaf. In addition, in the same manner, the number of lesions on untreated leaves subjected to a spread test with acetone water that does not contain the compound of the present invention was counted, and the control value (%) was calculated from these values. The results are shown in Table 2 below. It was hot. 【table】
Claims (1)
原子を示す。Ａはメチン（―CH＝）または窒素
原子（―Ｎ＝）を示す。〕 で表わされることを特徴とするトリハロプロパン
誘導体。[Claims] 1. General formula [In the formula, R 1 represents a lower alkyl group and X represents a halogen atom. A represents methine (-CH=) or nitrogen atom (-N=). ] A trihalopropane derivative characterized by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11815879A JPS5643262A (en) | 1979-09-13 | 1979-09-13 | Trihalopropane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11815879A JPS5643262A (en) | 1979-09-13 | 1979-09-13 | Trihalopropane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5643262A JPS5643262A (en) | 1981-04-21 |
| JPS645026B2 true JPS645026B2 (en) | 1989-01-27 |
Family
ID=14729529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11815879A Granted JPS5643262A (en) | 1979-09-13 | 1979-09-13 | Trihalopropane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5643262A (en) |
-
1979
- 1979-09-13 JP JP11815879A patent/JPS5643262A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5643262A (en) | 1981-04-21 |
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