JPH0386863A - Aminotrifluoromethylpyridine compound and its production - Google Patents
Aminotrifluoromethylpyridine compound and its productionInfo
- Publication number
- JPH0386863A JPH0386863A JP10795590A JP10795590A JPH0386863A JP H0386863 A JPH0386863 A JP H0386863A JP 10795590 A JP10795590 A JP 10795590A JP 10795590 A JP10795590 A JP 10795590A JP H0386863 A JPH0386863 A JP H0386863A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- trifluoromethyl
- ammonia
- bis
- pyridine
- 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
- -1 Aminotrifluoromethylpyridine compound Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- JLFVZLNEALJLLS-UHFFFAOYSA-N 4,6-bis(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=N1 JLFVZLNEALJLLS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 3
- NZFDZFJVWFDFQV-UHFFFAOYSA-N 2,4-bis(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC(C(F)(F)F)=C1 NZFDZFJVWFDFQV-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 23
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 229910021529 ammonia Inorganic materials 0.000 abstract description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 230000001473 noxious effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RRNXYHYDSDAOFW-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CN=C1C(F)(F)F RRNXYHYDSDAOFW-UHFFFAOYSA-N 0.000 description 2
- XZKZVCLLDKWOKM-UHFFFAOYSA-N 2-(trifluoromethyl)pyridin-3-amine Chemical class NC1=CC=CN=C1C(F)(F)F XZKZVCLLDKWOKM-UHFFFAOYSA-N 0.000 description 2
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical class FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 2
- OMRCXTBFBBWTDL-UHFFFAOYSA-N 3-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=CC(Cl)=C1 OMRCXTBFBBWTDL-UHFFFAOYSA-N 0.000 description 2
- RWGBXAQMUBGGKQ-UHFFFAOYSA-N 4-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC(C(F)(F)F)=CC=N1 RWGBXAQMUBGGKQ-UHFFFAOYSA-N 0.000 description 2
- NJFRBMFEAGFNDC-UHFFFAOYSA-N 5-(trifluoromethyl)pyridin-3-amine Chemical compound NC1=CN=CC(C(F)(F)F)=C1 NJFRBMFEAGFNDC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- GBNPVXZNWBWNEN-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC(Cl)=C1 GBNPVXZNWBWNEN-UHFFFAOYSA-N 0.000 description 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、種々の有害生物を防除することができる化合
物又は医薬の有効成分化合物に容易に誘導することがで
きる中間体としての新規なアミノトリフルオロメチルピ
リジン系化合物並びにその製造方法に関する。Detailed Description of the Invention (Industrial Application Field) The present invention provides novel amino acids as intermediates that can be easily derived into compounds capable of controlling various harmful organisms or active ingredient compounds of pharmaceuticals. This invention relates to trifluoromethylpyridine compounds and their production methods.
（発明の開示）
本発明の第１の発明は、２−アミノ−４，６−ビス（ト
リフルオロメチル）ピリジンに関する。(Disclosure of the Invention) The first invention of the present invention relates to 2-amino-4,6-bis(trifluoromethyl)pyridine.
本発明の第２の発明は、２−ハロゲノ−４，６−ビス（
トリフルオロメチル〉ピリジンとアンモニアとを反応さ
せて２−アミノ−４，６−ビス（トリフルオロメチル）
ピリジンを製造するアミノトリフルオロメチルピリジン
系化合物の製造方法である。The second invention of the present invention is 2-halogeno-4,6-bis(
Trifluoromethyl> 2-amino-4,6-bis(trifluoromethyl) by reacting pyridine and ammonia
This is a method for producing an aminotrifluoromethylpyridine compound to produce pyridine.
本発明の２−アミノ−４，６−ビス（トリフルオロメチ
ル）ピリジン（以下、アミノトリフルオロメチルピリジ
ン系化合物という）は、例えば２−ハロゲノ−４，６−
ビス（トリフルオロメチル）ピリジン（以下、ハロゲノ
トリフルオロメチルピリジン系化合物という）とアンモ
ニアとを反応させることにより製造することができる。The 2-amino-4,6-bis(trifluoromethyl)pyridine (hereinafter referred to as an aminotrifluoromethylpyridine compound) of the present invention is, for example, 2-halogeno-4,6-
It can be produced by reacting bis(trifluoromethyl)pyridine (hereinafter referred to as a halogenotrifluoromethylpyridine compound) and ammonia.
上記方法を実施するにあたって、−ａ的には、オートク
レーブなどの密閉容器内に、ハロゲノトリフルオロメチ
ルピリジン系化合物とあらかじめ水にアンモニアを溶解
させたアンモニア水とを入れるか、或はハロゲノトリフ
ルオロメチルピリジン系化合物中へ液安を導入するかし
て、５０〜２００℃、望ましくは１００〜１８０℃の温
度で反応させる０本反応温度が前記範囲を超えると目的
物が分解し易く、一方低すぎると所望の反応が進まない
０水反応では、触媒、例えば塩化第１銅を存在させても
よく、その存在量としてはハロゲノトリフルオロメチル
ピリジン系化合物１００重量部に対して１〜３０重量部
である。アンモニアとしてアンモニア水を用いる場合は
、通常２０％以上、望ましくは２８〜４０％の濃度のも
のを使用する。アンモニアの使用量は、ハロゲノトリフ
ルオロメチルピリジン系化合物１モルに対して１モル以
上、望ましくは３〜３０モルである０反応時の圧力は密
閉容器内での加温により２〜１２０気圧程度になり、ま
た反応時間は５時間以上、望ましくは５〜１００時間で
ある。In carrying out the above method, -a, a halogenotrifluoromethylpyridine compound and aqueous ammonia in which ammonia is dissolved in water in advance are placed in a closed container such as an autoclave, or a halogenotrifluoromethyl By introducing liquid ammonium into the pyridine compound, the reaction is carried out at a temperature of 50 to 200°C, preferably 100 to 180°C.If the reaction temperature exceeds the above range, the target product is likely to decompose, but on the other hand, it is too low. In the zero water reaction in which the desired reaction does not proceed, a catalyst such as cuprous chloride may be present, and the amount thereof is 1 to 30 parts by weight per 100 parts by weight of the halogenotrifluoromethylpyridine compound. be. When aqueous ammonia is used as ammonia, it is usually at a concentration of 20% or more, preferably 28 to 40%. The amount of ammonia used is 1 mol or more, preferably 3 to 30 mol, per 1 mol of the halogenotrifluoromethylpyridine compound.The pressure during the reaction is about 2 to 120 atmospheres by heating in a closed container. The reaction time is 5 hours or more, preferably 5 to 100 hours.
反応生成物を放冷し、通常は塩化メチレン、ベンゼン、
エチルエーテルなどの溶媒で抽出した後、溶媒を留去し
、必要により通常の蒸留を行なって目的物を得る０反応
生成物中の目的物は油状物質或は結晶として得られ、上
記抽出により不純物を除くことができる。またアンモニ
アとしてアンモニア水を使用した場合に、反応生成物の
水層中に目的物が含まれることもあるが、前述の抽出処
理によって目的物を充分回収することができる。The reaction product is allowed to cool and is usually mixed with methylene chloride, benzene,
After extraction with a solvent such as ethyl ether, the solvent is distilled off, and if necessary, ordinary distillation is performed to obtain the target product.The target product in the reaction product is obtained as an oily substance or crystals, and the above extraction removes impurities. can be excluded. Further, when aqueous ammonia is used as ammonia, the target product may be contained in the aqueous layer of the reaction product, but the target product can be sufficiently recovered by the above-mentioned extraction process.
次に本発明のアミノトリフルオロメチルピリジン系化合
物の具体的合成例を記載する。Next, a specific synthesis example of the aminotrifluoromethylpyridine compound of the present invention will be described.
参考例１． ３−ア果ノー５−トリフルオロメチルピ
リジンの合成
３００−のオートクレーブに、３−クロロ−５＝トリフ
ルオロメチルピリジン４０．８ ｇと塩化第１銅１２．
２ｇと液安７６．５ｇを入れ、１５０℃で６３時間反応
させた（内圧は約１２０気圧）。Reference example 1. Synthesis of 3-chloro-5-trifluoromethylpyridine 40.8 g of 3-chloro-5-trifluoromethylpyridine and 12.5 g of cuprous chloride were placed in a 300-liter autoclave.
2g and 76.5g of liquid ammonium were added and reacted at 150°C for 63 hours (internal pressure was about 120 atm).
反応終了後放冷して、水層と油層からなる反応生成物を
得、この水層を分離して塩化メチレンで抽出した。塩化
メチレンを留去し、通常の蒸留を行なって、３−アミノ
−５−トリフルオロメチルピリジン（沸点１０５．５〜
ｂ１１ｓｎｔ１ｇ） ２５．３ｇを得た。After the reaction was completed, the mixture was allowed to cool to obtain a reaction product consisting of an aqueous layer and an oil layer, and the aqueous layer was separated and extracted with methylene chloride. The methylene chloride was distilled off and a conventional distillation was performed to obtain 3-amino-5-trifluoromethylpyridine (boiling point 105.5~
b11snt1g) 25.3g was obtained.
参考例２． ２−アミノ−４−トリフルオロメチルピリ
ジンの合成
２００ Ｉｄのオートクレーブに、２−クロロ−４−ト
リフルオロメチルピリジン１４．５ｇと２８％のアンモ
ニア水１０８−を入れ、１８０℃で１０時間反応させた
く内圧は約２０気圧）。Reference example 2. Synthesis of 2-amino-4-trifluoromethylpyridine 14.5 g of 2-chloro-4-trifluoromethylpyridine and 28% aqueous ammonia were placed in a 200 Id autoclave and reacted at 180°C for 10 hours. Internal pressure is approximately 20 atmospheres).
反応終了後放冷し、得られた結晶物を水洗、乾燥し、２
−アミノ−４−トリフルオロメチルピリジン（融点６９
〜７０℃）１０．２ ｇを得た。After the reaction was completed, it was allowed to cool, and the obtained crystalline product was washed with water, dried, and
-amino-4-trifluoromethylpyridine (melting point 69
~70°C) 10.2 g was obtained.
実施例 ２−アミノ−４，６−ビス（トリフルオロ
メチル）ピリジンの合成
２００１１１のオートクレーブに、２−クロロ−４，６
−ビス（トリフルオロメチル）ピリジン２５ｇと４０％
のアンモニア水８５ｇを入れ、１５０℃で５時間反応さ
せた（内圧は約２６気圧）。Example Synthesis of 2-amino-4,6-bis(trifluoromethyl)pyridine In a 200111 autoclave, 2-chloro-4,6
-25g of bis(trifluoromethyl)pyridine and 40%
85 g of ammonia water was added thereto, and the mixture was reacted at 150° C. for 5 hours (internal pressure was about 26 atm).
反応終了後放冷し、得られた結晶物を水洗、乾燥し、２
−アミノ−４，６−ビス（トリフルオロメチル）ピリジ
ン（融点７０．８〜７１．２℃）１６．５ｇを得た。After the reaction was completed, it was allowed to cool, and the obtained crystalline product was washed with water, dried, and
16.5 g of -amino-4,6-bis(trifluoromethyl)pyridine (melting point 70.8-71.2°C) was obtained.
本発明のアミノトリフルオロメチルピリジン系化合物は
下記の参考例に記載の方法で化合動磁１〜４に誘導でき
る。The aminotrifluoromethylpyridine compounds of the present invention can be induced into compound magnetisms 1 to 4 by the method described in the Reference Examples below.
ｌＨＭ３． Ｎ−（２，６−ジフルオロベンゾイル）
−Ｎ’ −（５−トリフルオ
ロメチル−３−ピリジル）ウレア
（化合物弘１）の合成
３−アミノ−５−トリフルオロメチルピリジン１．０ｇ
をジオキサン５−に溶解し、この溶液に２．６−シフル
オロベンゾイルイソシアネート１．３５ ｇとジオキサ
ン２１１１の溶液を滴下し室温で約１時間撹拌した。lHM3. N-(2,6-difluorobenzoyl)
Synthesis of -N'-(5-trifluoromethyl-3-pyridyl)urea (compound Hiroshi 1) 1.0 g of 3-amino-5-trifluoromethylpyridine
was dissolved in dioxane 5-, and a solution of 1.35 g of 2,6-cyfluorobenzoyl isocyanate and dioxane 2111 was added dropwise to this solution, followed by stirring at room temperature for about 1 hour.
反応終了後、反応物を約１００−の水に投入し、析出し
た結晶を濾取し、メタノールで洗浄した後、乾燥を行な
い、Ｎ−（２，６−ジフルオロベンゾイル）−Ｎ’
−（５−）リフルオロメチル−３−ピリジル）ウレア（
融点２３３〜２３５℃〉１．７３ ｇを得た。After completion of the reaction, the reaction product was poured into about 100 ml of water, and the precipitated crystals were collected by filtration, washed with methanol, and dried to give N-(2,6-difluorobenzoyl)-N'
-(5-)lifluoromethyl-3-pyridyl)urea (
Melting point 233-235°C>1.73 g was obtained.
参考例４． Ｎ−（２，６−ジフルオロベンゾイル）
−Ｎ’ −（４−トリフルオ
ロメチル−２−ピリジル）ウレア
（化合物思２）の合成
２−アミノ−４−トリフルオロメチルピリジン０．５０
ｇをジオキサン７ＩＲ１に溶解し、このｉ容液を２．
６−シフルオロベンゾイルイソシアネート０．５６ｇと
ジオキサン７−の溶液に滴下し室温で約１５時間撹拌し
た。Reference example 4. N-(2,6-difluorobenzoyl)
Synthesis of -N'-(4-trifluoromethyl-2-pyridyl)urea (compound idea 2) 2-amino-4-trifluoromethylpyridine 0.50
Dissolve g in dioxane 7IR1 and add 1 volume of this solution to 2.
The mixture was added dropwise to a solution of 0.56 g of 6-cyfluorobenzoyl isocyanate and dioxane 7- and stirred at room temperature for about 15 hours.
反応終了後、反応物を約１００−の水に投入し、析出し
た結晶を濾取し、水洗した後、乾燥を行ない、Ｎ−（２
，６−ジフルオロベンゾイル）Ｎ’ −（４−）リフ
ルオロメチル−２−ピリジル）ウレア（融点１６７〜１
６９℃） １．０ｇを得た。After completion of the reaction, the reaction product was poured into about 100 ml of water, and the precipitated crystals were collected by filtration, washed with water, and dried to give N-(2
,6-difluorobenzoyl)N'-(4-)lifluoromethyl-2-pyridyl)urea (melting point 167-1
69°C) 1.0g was obtained.
参考例５． Ｎ−（２，６−ジフルオロベンゾイル）
−Ｎ’ −（２，４−ビス（トリフルオロメチル）−
６−ピリジ
ル〕ウレア（化合物ぬ３）の合成
２−アミノ−４，６−ビス（トリフルオロメチル）ピリ
ジン２．２ｇをジオキサン１０ｍに溶解し、その溶液を
２．６−シフルオロベンゾイルイソシアネート１．９ｇ
とジオキサン２０−の溶液に滴下し室温で約１時間反応
させた。Reference example 5. N-(2,6-difluorobenzoyl)
-N'-(2,4-bis(trifluoromethyl)-
Synthesis of 6-pyridyl]urea (compound No. 3) 2.2 g of 2-amino-4,6-bis(trifluoromethyl)pyridine was dissolved in 10 m of dioxane, and the solution was dissolved in 2.6-cyfluorobenzoyl isocyanate 1. 9g
was added dropwise to a solution of dioxane 20- and reacted at room temperature for about 1 hour.
反応終了後、反応物を４０〜５０℃の温水約２００−に
投入し、析出した結晶を濾取した後、乾燥を行ない、Ｎ
−（２，６−ジフルオロベンゾイル）−Ｎ’ −（２
，４−ビス（トリフルオロメチル）−６−ピリジルコウ
レア（融点１５１．５〜１５２．５℃）８．２ｇを得た
。After the reaction, the reaction product was poured into about 200°C of warm water at 40 to 50°C, and the precipitated crystals were collected by filtration and dried.
-(2,6-difluorobenzoyl)-N' -(2
, 8.2 g of 4-bis(trifluoromethyl)-6-pyridylcourea (melting point 151.5-152.5°C) was obtained.
参考例６． Ｎ−（２，４−ビス（トリフルオロメチ
ル）−６−ピリジル）−２，６−
シニトロー３−クロロ−４−トリ
フルオロメチルアニリン（化合物
阻４〉の合成
２−アミノ−４，６−ビス（トリフルオロメチル）ピリ
ジン１．５ｇをジオキサン３０−に溶解し、撹拌しなが
ら粉末状の水酸化カリウム１．５ｇを添加した。その後
、２．４−ジクロロ−３，５−ジニトロベンシトリフル
オライド２．３ｇを添加し、約１５時間撹拌させた。Reference example 6. Synthesis of N-(2,4-bis(trifluoromethyl)-6-pyridyl)-2,6-sinitro-3-chloro-4-trifluoromethylaniline (compound 4) 2-amino-4,6-bis 1.5 g of (trifluoromethyl)pyridine was dissolved in dioxane 30- and 1.5 g of powdered potassium hydroxide was added with stirring. Then, 2,4-dichloro-3,5-dinitrobencitrifluoride 2 .3g was added and allowed to stir for about 15 hours.
反応終了後、生成物を希硫酸溶液に投入し、塩化メチレ
ンで抽出した。抽出層を水洗、乾燥させて溶媒を留去し
、結晶化させ、その結晶をヘキサンで洗浄した後乾燥し
て目的物２．０ｇ （融点１６９〜１７０℃）を得た。After the reaction was completed, the product was poured into a dilute sulfuric acid solution and extracted with methylene chloride. The extracted layer was washed with water and dried to remove the solvent and crystallize. The crystals were washed with hexane and dried to obtain 2.0 g of the desired product (melting point: 169-170°C).
前記アミノトリフルオロメチルピリジン系化合物から誘
導された前記化合物Ｎ＆１〜４は、有害生物肪除剤とし
て有用である。化合物ぬ１〜３は特に有害昆虫の防除に
有効であり、例えば１１００ｐｐの濃度における２〜３
令のコナガに対する殺虫試験で１００％の殺虫効果を示
し、また１０ｐｐ−の濃度における２〜３令のハスモン
ヨトウに対する殺虫試験で１００％の殺虫効果を示す。The compounds N&1 to 4 derived from the aminotrifluoromethylpyridine compounds are useful as pest control agents. Compounds 1 to 3 are particularly effective in controlling harmful insects, for example 2 to 3 at a concentration of 1100 pp.
It shows a 100% insecticidal effect in an insecticidal test against the instar diamondback moth, and also shows a 100% insecticidal effect in an insecticidal test against the 2nd to 3rd instar Spodoptera at a concentration of 10 pp-.
さらに化合物Ｍ４は、特に農園芸用殺菌剤として有用で
ある０例えばキュウリ灰色かび病およびべと病に対し、
１１００ｐｐの薬液散布（予防効果）試験で、発病を完
全に抑えた。（これらの試験方法の詳細は、特開昭５４
−１２５６７７号公報及び同５６−９２２７２号公報に
準じた）。Furthermore, compound M4 is particularly useful as an agricultural and horticultural fungicide, for example against gray mold and downy mildew of cucumbers.
In a test of spraying 1100pp of chemical solution (preventive effect), the onset of the disease was completely suppressed. (Details of these test methods can be found in JP-A-54
-125677 and 56-92272).
Claims (2)
）ピリジン。(1) 2-amino-4,6-bis(trifluoromethyl)pyridine.
ル）ピリジンとアンモニアとを反応させて２−アミノ−
４，６−ビス（トリフルオロメチル）ピリジンを製造す
ることを特徴とするアミノトリフルオロメチルピリジン
系化合物の製造方法。(2) 2-Amino-
A method for producing an aminotrifluoromethylpyridine compound, the method comprising producing 4,6-bis(trifluoromethyl)pyridine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10795590A JPH0386863A (en) | 1990-04-24 | 1990-04-24 | Aminotrifluoromethylpyridine compound and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10795590A JPH0386863A (en) | 1990-04-24 | 1990-04-24 | Aminotrifluoromethylpyridine compound and its production |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60295171A Division JPS62155259A (en) | 1985-12-27 | 1985-12-27 | Aminotrifluoromethylpyridine and its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0386863A true JPH0386863A (en) | 1991-04-11 |
| JPH0575744B2 JPH0575744B2 (en) | 1993-10-21 |
Family
ID=14472297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10795590A Granted JPH0386863A (en) | 1990-04-24 | 1990-04-24 | Aminotrifluoromethylpyridine compound and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0386863A (en) |
-
1990
- 1990-04-24 JP JP10795590A patent/JPH0386863A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0575744B2 (en) | 1993-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |