JPS6147832B2 - - Google Patents
Info
- Publication number
- JPS6147832B2 JPS6147832B2 JP12292182A JP12292182A JPS6147832B2 JP S6147832 B2 JPS6147832 B2 JP S6147832B2 JP 12292182 A JP12292182 A JP 12292182A JP 12292182 A JP12292182 A JP 12292182A JP S6147832 B2 JPS6147832 B2 JP S6147832B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- water
- reaction
- compound
- methoxyphenyl
- 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
Links
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ZFMZSZMUFWRAOG-UHFFFAOYSA-N 3-methoxy-n-methylaniline Chemical compound CNC1=CC=CC(OC)=C1 ZFMZSZMUFWRAOG-UHFFFAOYSA-N 0.000 claims description 2
- BEHROHNZLKXFQV-UHFFFAOYSA-N o-naphthalen-2-yl n-(3-methoxyphenyl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C3C=CC=CC3=CC=2)=C1 BEHROHNZLKXFQV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000004780 naphthols Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 10
- 230000002363 herbicidal effect Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 241000209094 Oryza Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- -1 (3-methoxyphenyl)-N-methylthiocarbamate Chemical compound 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 235000003840 Amygdalus nana Nutrition 0.000 description 1
- 244000296825 Amygdalus nana Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000218691 Cupressaceae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 235000011432 Prunus Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PKDYOBNDEKFDQW-UHFFFAOYSA-N n-(3-methoxyphenyl)-n-methylcarbamothioyl chloride Chemical compound COC1=CC=CC(N(C)C(Cl)=S)=C1 PKDYOBNDEKFDQW-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- INFPIPCTRVDPJG-UHFFFAOYSA-N o-naphthalen-2-yl chloromethanethioate Chemical compound C1=CC=CC2=CC(OC(=S)Cl)=CC=C21 INFPIPCTRVDPJG-UHFFFAOYSA-N 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000014774 prunus Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、ナフチルチオカーバメートおよびそ
の製造法に関する。
従来、アリールチオカーバメート系化合物が医
薬として抗菌性、殺線虫性を有することは周知で
ある。また置換フエニルカーバメート系化合物を
除草剤として使用し得ることが開示されている。
本発明者らは、ナフチルチオカーバメート誘導
体で十分な除草効果を有し、かつ、高度の選択性
を有する化合物を開発すべく、鋭意研究を重ねた
結果、移植水稲に対して薬害がなく、ノビエその
他の一般雑草に対して選択的に高い除草効果を示
す文献未記載の化合物を見い出し、本発明を完成
した。
すなわち、本発明はＯ―２―ナフチル Ｎ―
（３―メトキシフエニル）―Ｎ―メチルチオカー
バメート（以下本発明化合物という）およびその
製造法を提供するものである。
本発明化合物は高い除草効果を有する。本発明
化合物を有効成分とする除草剤は、水田除草剤と
して優れた選択殺草活性を示し、移植水稲には無
害で、ノビエをはじめとする多くの水田雑草を有
効に防除する能力を有する。
本発明化合物は、下記反応式に従つて製造する
ことができる。
（式中、Halはハロゲン原子を示す。）
上記の反応は、脱ハロゲン化水素剤の存在下、
さらに反応溶媒の存在下あるいは不存在下に、通
常、０℃から150℃の反応温度で進行し、反応時
間は数分ないし48時間程度である。
脱ハロゲン化水素剤としては、水酸化ナトリウ
ム，水酸化カリウム等の水酸化アルカリ，水酸化
カルシウム等の水酸化アルカリ土類、炭酸ナトリ
ウム，炭酸カリウム，炭酸水素ナトリウム，炭酸
水素カリウム等の炭酸アルカリ塩、水素化ナトリ
ウムのような水素化金属、トリエチルアミン，ジ
メチルアニリン，ピリジン等の第三級アミン等を
挙げることができる。反応式(2)においては、原料
の３―メトキシ―Ｎ―メチルアニリンを脱ハロゲ
ン化水素剤として使用できる。
反応溶媒としては、水およびメタノール，エタ
ノール，イソプロパノール等のアルコール類、ア
セトン，メチルエチルケトン等のケトン類、ベン
ゼン，トルエン，キシレン等の芳香族炭化水素
類、エチルエーテル，テトラヒドロフラン，ジオ
キサン等のエーテル類、クロルベンゼン，クロロ
ホルム，四塩化炭素，ジクロロエタン等のハロゲ
ン化炭化水素類、ジメチルホルムアミド，ジメチ
ルスルホキシド等の極性溶媒等が用いられる。
次に本発明化合物の製造方法を具体的に説明す
る。
〔実施例 １〕
Ｎ―（３―メトキシフエニル）―Ｎ―メチルチ
オカルバモイルクロライド2.00ｇ、β―ナフトー
ル1.44ｇおよび無水炭酸カリウム1.66ｇをメチル
エチルケトン50mlに添加し、15時間加熱還流し
た。反応混合物を室温まで冷却した後、水に注
ぎ、生成物をベンゼンで抽出した。
ベンゼン溶液を水、飽和塩化ナトリウム水溶液
の順で洗い、無水硫酸マグネシウムで乾燥した
後、減圧下でベンゼンを留去した。残留物をカラ
ムクロマトグラフイー（シリカゲル，ベンゼン展
開）で精製し、Ｏ―２―ナフチル Ｎ―（３―メ
トキシフエニル）―Ｎ―メチルチオカーバメート
の結晶1.45ｇ（収率45％）を得た。
融点：93〜94℃（エタノールから再結晶）
元素分析
Ｃ（％） Ｈ（％） Ｎ
（％）
実測値 70.25 5.39 4.72
計算値 70.57 5.30 4.33
核磁気共鳴スペクトル（δ＝ppm，CDCl3）
3.66（3H，Ｓ），3.73（3H，Ｓ），6.66〜7.90
（11H，ｍ）
赤外吸収スペクトル（cm-1，KBr）
1595，1580，1465，1425，1360
質量分析スペクトル
親ピーク：323（分子量323），フラグメン
ト・ピーク：180，164
〔実施例 ２〕
３―メトキシ―Ｎ―メチルアニリン1.37ｇおよ
び無水炭酸カリウム1.66ｇをアセトン20mlに添加
し、室温で撹拌しながら、これにＯ―２―ナフチ
ル クロルチオホルメイト2.23ｇをアセトン20ml
に溶かして滴下した。このまま15時間撹拌してか
ら、反応混合物を冷水に注ぎ、エチルエーテルで
抽出した。エーテル溶液を希塩酸，水の順序で洗
い、無水硫酸マグネシウムで乾燥した。エーテル
を留去し、得られた固体をエタノールから再結晶
し2.94ｇ（収率91％）を得た。このものは実施例
１で得られた結晶と同一であつた。
本発明化合物の殺草スペクトラムは水田の主要
害草ノビエ，タマガヤツリに対して卓効を示し、
コナギ，キカシグサ等の広葉雑草に対しても強い
効果を示す。
稚苗移植水稲に対する安全性は極めて高く、
1000ｇ／10aでも影響は全くみられず、極めて優
れた選択除草活性が得られた。
次に、本発明化合物の除草効果を〔参考例〕に
よつて説明する。
〔参考例〕
直径９cmの磁製ポツトに水田土壌を入れ、水を
加えて代かき後、土壌表層に雑草種子を播き、２
葉期の水稲苗（品種、日本晴）を１cmの深さに、
２本２株植えとした。翌日２cmの湛水を行ない、
本発明化合物10部を担体材料としてジークライト
〔商品名、国峰工業(株)製〕87.3部、界面活性剤と
してネオペレツクス〔商品名、花王アトラス(株)
製〕1.35部およびソルポール800A〔商品名、東
邦化学工業(株)製〕1.35部と共に混合粉砕して得た
水和剤の所定薬量をポツト当り10mlの水に希釈し
て水面に滴下処理した。
その後、温室に静置し、処理20日後に除草効果
および水稲に及ぼした影響を調査した。
評価は６段階で表示したが、具体的には下記の
通りである。その結果は第１表および第２表に示
した。
The present invention relates to naphthylthiocarbamate and its production method. It is well known that arylthiocarbamate compounds have antibacterial and nematocidal properties as medicines. It is also disclosed that substituted phenyl carbamate compounds can be used as herbicides. The present inventors have conducted extensive research to develop a naphthylthiocarbamate derivative with sufficient herbicidal effects and a high degree of selectivity. The present invention was completed by discovering a compound that has not been described in any literature that exhibits selectively high herbicidal effects against other common weeds. That is, the present invention provides O-2-naphthyl N-
The present invention provides (3-methoxyphenyl)-N-methylthiocarbamate (hereinafter referred to as the compound of the present invention) and a method for producing the same. The compounds of the present invention have high herbicidal effects. The herbicide containing the compound of the present invention as an active ingredient exhibits excellent selective herbicidal activity as a paddy field herbicide, is harmless to transplanted paddy rice, and has the ability to effectively control many paddy field weeds including field weed. The compound of the present invention can be produced according to the following reaction formula. (In the formula, Hal represents a halogen atom.) The above reaction is carried out in the presence of a dehydrohalogenating agent,
Further, the reaction usually proceeds in the presence or absence of a reaction solvent at a reaction temperature of 0°C to 150°C, and the reaction time is about several minutes to 48 hours. Examples of dehydrohalogenation agents include alkali hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth hydroxides such as calcium hydroxide, and alkali carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate. , metal hydrides such as sodium hydride, and tertiary amines such as triethylamine, dimethylaniline, and pyridine. In reaction formula (2), the raw material 3-methoxy-N-methylaniline can be used as a dehydrohalogenating agent. Reaction solvents include water, alcohols such as methanol, ethanol, and isopropanol, ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, and xylene, ethers such as ethyl ether, tetrahydrofuran, and dioxane, and chlorine. Halogenated hydrocarbons such as benzene, chloroform, carbon tetrachloride and dichloroethane, polar solvents such as dimethylformamide and dimethyl sulfoxide, etc. are used. Next, the method for producing the compound of the present invention will be specifically explained. [Example 1] 2.00 g of N-(3-methoxyphenyl)-N-methylthiocarbamoyl chloride, 1.44 g of β-naphthol and 1.66 g of anhydrous potassium carbonate were added to 50 ml of methyl ethyl ketone, and the mixture was heated under reflux for 15 hours. After the reaction mixture was cooled to room temperature, it was poured into water and the product was extracted with benzene. The benzene solution was washed with water and a saturated aqueous sodium chloride solution in that order, dried over anhydrous magnesium sulfate, and then benzene was distilled off under reduced pressure. The residue was purified by column chromatography (silica gel, developed with benzene) to obtain 1.45 g (45% yield) of crystals of O-2-naphthyl N-(3-methoxyphenyl)-N-methylthiocarbamate. Melting point: 93-94℃ (recrystallized from ethanol) Elemental analysis C (%) H (%) N
(%) Actual value 70.25 5.39 4.72 Calculated value 70.57 5.30 4.33 Nuclear magnetic resonance spectrum (δ=ppm, CDCl3 ) 3.66 (3H, S), 3.73 (3H, S), 6.66-7.90
(11H, m) Infrared absorption spectrum (cm -1 , KBr) 1595, 1580, 1465, 1425, 1360 Mass spectrometry spectrum Parent peak: 323 (molecular weight 323), Fragment peak: 180, 164 [Example 2] 3 1.37 g of -methoxy-N-methylaniline and 1.66 g of anhydrous potassium carbonate are added to 20 ml of acetone, and while stirring at room temperature, 2.23 g of O-2-naphthyl chlorothioformate is added to 20 ml of acetone.
It was dissolved in and dripped. After stirring for 15 hours, the reaction mixture was poured into cold water and extracted with ethyl ether. The ether solution was washed with dilute hydrochloric acid and water in that order, and dried over anhydrous magnesium sulfate. The ether was distilled off, and the resulting solid was recrystallized from ethanol to obtain 2.94 g (yield: 91%). This crystal was the same as the crystal obtained in Example 1. The herbicidal spectrum of the compound of the present invention shows excellent efficacy against the major pests of paddy fields, the grasshopper and cypress.
It is also highly effective against broad-leaved weeds such as Prunus japonicus and Kikashigusa. The safety of transplanted paddy rice seedlings is extremely high.
Even at 1000g/10a, no effect was observed at all, and extremely excellent selective herbicidal activity was obtained. Next, the herbicidal effects of the compounds of the present invention will be explained using [Reference Examples]. [Reference example] Paddy soil was poured into a porcelain pot with a diameter of 9 cm, water was added, and weed seeds were sown on the surface layer of the soil.
Paddy rice seedlings (variety, Nipponbare) in the leaf stage are planted at a depth of 1 cm.
Two plants were planted. The next day, we flooded the area with 2 cm of water.
10 parts of the compound of the present invention as a carrier material, 87.3 parts of Sieglite [trade name, manufactured by Kunio Kogyo Co., Ltd.], and as a surfactant, Neoperex [trade name, manufactured by Kao Atlas Co., Ltd.]
A predetermined amount of a wettable powder obtained by mixing and pulverizing 1.35 parts of Solpol 800A [trade name, manufactured by Toho Chemical Industry Co., Ltd.] was diluted in 10 ml of water per pot and dropped onto the water surface. . Thereafter, the mixture was left in a greenhouse, and 20 days after treatment, the herbicidal effect and the effect on paddy rice were investigated. The evaluation was displayed on a 6-level scale, and the specific details are as follows. The results are shown in Tables 1 and 2.
【表】【table】
【表】【table】
Claims (1)
ニル）―Ｎ―メチルチオカーバメート ２ 一般式 （式中、Ｘは水素又はハロチオカルボニル基で
ある。）ナフトール誘導体を、 一般式 （式中、Ｙは前式のＸが水素原子のときハロチ
オカルボニル基であり、前式のＸがハロチオカル
ボニル基のとき水素原子である。）で表わされる
３―メトキシ―Ｎ―メチルアニリン誘導体と反応
させることを特徴とするＯ―２―ナフチル Ｎ―
（３―メトキシフエニル）―Ｎ―メチルチオカ―
バメートの製造法。[Claims] 1 O-2-naphthyl N-(3-methoxyphenyl)-N-methylthiocarbamate 2 General formula (In the formula, X is hydrogen or a halothiocarbonyl group.) The naphthol derivative is represented by the general formula 3-methoxy-N-methylaniline represented by O-2-naphthyl N- characterized by reacting with a derivative
(3-methoxyphenyl)-N-methylthiocar-
Method for producing bamate.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12292182A JPS5951257A (en) | 1982-07-16 | 1982-07-16 | Naphthylthiocarbamate derivative and its preparation |
| DE8383102600T DE3360819D1 (en) | 1982-03-17 | 1983-03-16 | Carbamate derivatives, process for producing the same and herbicides comprising the compounds as an effective component |
| EP83102600A EP0090263B1 (en) | 1982-03-17 | 1983-03-16 | Carbamate derivatives, process for producing the same and herbicides comprising the compounds as an effective component |
| US06/476,313 US4551169A (en) | 1982-03-17 | 1983-03-17 | Metamethoxy aryl carbamate derivatives and herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12292182A JPS5951257A (en) | 1982-07-16 | 1982-07-16 | Naphthylthiocarbamate derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5951257A JPS5951257A (en) | 1984-03-24 |
| JPS6147832B2 true JPS6147832B2 (en) | 1986-10-21 |
Family
ID=14847896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12292182A Granted JPS5951257A (en) | 1982-03-17 | 1982-07-16 | Naphthylthiocarbamate derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5951257A (en) |
-
1982
- 1982-07-16 JP JP12292182A patent/JPS5951257A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5951257A (en) | 1984-03-24 |
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