JPH0761925B2 - Herbicide composition - Google Patents
Herbicide compositionInfo
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- JPH0761925B2 JPH0761925B2 JP61249196A JP24919686A JPH0761925B2 JP H0761925 B2 JPH0761925 B2 JP H0761925B2 JP 61249196 A JP61249196 A JP 61249196A JP 24919686 A JP24919686 A JP 24919686A JP H0761925 B2 JPH0761925 B2 JP H0761925B2
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Description
【発明の詳細な説明】 (産業上の利用分野) 本発明は、新しい除草剤組成物に関するものであり、雑
草と作物との間に高い選択性を有する除草剤を提供する
ことにある。Description: TECHNICAL FIELD The present invention relates to a new herbicide composition, and to provide a herbicide having high selectivity between weeds and crops.
(従来の技術) 除草剤は近縁の高等植物間における選択毒性を利用する
ものであり、通常の使用条件下で使用されている場合に
は作物に対する薬害は生じることはない。しかし、例え
ば水稲栽培において特殊の条件下、すなわち、土壌条
件、気象条件、水稲の生理条件、除草剤の散布上の悪条
件、その他の悪条件が組み合わさった場合に往々にして
水稲に薬害を与えることがある。水田入水後に未分解の
有機物が残るような多量の未熟有機物の施用、透水及び
通気の不良、水田の老朽化、水田入水後の異常昇温など
が関与すると水田土壌の強還元化が惹起され、この様な
還元状態では薬剤の植物体内での分解能も弱まり、除草
剤の多量散布、またはむらまきにより水稲に薬害を与え
ることがある。本発明に係わるS−(4−クロロベンジ
ル)N,N−ジエチルチオカルバマート(以下ベンチオカ
ーブと云う)も、これら悪条件では稲に薬害を与えるこ
とがある。(Prior Art) Herbicides utilize selective toxicity between closely related higher plants, and do not cause phytotoxicity to crops when used under normal use conditions. However, for example, when special conditions in paddy rice cultivation, that is, soil conditions, meteorological conditions, physiological conditions of paddy rice, adverse conditions for spraying herbicides, and other adverse conditions are combined, phytotoxicity is often applied to the paddy rice. May be given. Application of a large amount of immature organic matter such that undecomposed organic matter remains after entering the paddy field, poor permeation and aeration, deterioration of the paddy field, and abnormal temperature rise after entering the paddy field causes a strong reduction of the paddy field soil, In such a reduced state, the ability of the drug to decompose in the plant body is weakened, and the herbicide may be sprayed in large amounts or unevenly distributed to cause damage to rice plants. The S- (4-chlorobenzyl) N, N-diethylthiocarbamate (hereinafter referred to as "benchocarb") according to the present invention may also cause phytotoxicity to rice under these adverse conditions.
稲に対するベンチオカーブの有害作用を防ぐ物質はすで
に提供されている(特開昭58−105904号明細書、同58−
116403号明細書及び同58−128305号明細書)。Substances for preventing the harmful effects of bench iocarb on rice have already been provided (JP-A-58-105904, JP-A-58-105904).
116403 and 58-128305).
しかしながら、従来の解毒剤は、気象条件、とりわけ異
常高温や豪雨等又は土壌条件の性質等によって限定され
た作用領域を有するものであり、必らずしも十分な効果
を挙げることができなかった、この理由は例えば解毒剤
の物理化学的性質に起因するものと考えられる。However, conventional antidotes have a limited action area due to the nature of weather conditions, in particular, extremely high temperatures, heavy rainfall, or soil conditions, and thus have not necessarily exhibited sufficient effects. The reason for this is considered to be due to, for example, the physicochemical properties of the antidote.
(発明が解決しようとする問題点) 本発明者らは、これら悪条件においても薬害を生ずるこ
とのない除草剤を得るべく鋭意研究した結果、ベンチオ
カーブに特定のクロロメタンスルホン酸置換フェニルエ
ステル誘導体を配合することにより薬害を生ずることな
く、雑草と作物との間に高い選択性を有する除草剤が得
られることを見出し、本発明を完成したものである。(Problems to be Solved by the Invention) As a result of earnest research to obtain a herbicide which does not cause phytotoxicity even under these adverse conditions, the present inventors have found that a specific chloromethanesulfonic acid-substituted phenyl ester derivative was found to be bentocarb. The present invention has been completed by finding that a herbicide having high selectivity between weeds and crops can be obtained without causing phytotoxicity by compounding.
(問題点を解決するための手段) 本発明の除草剤組成物は、ベンチオカーブと 一般式 (式中、Xは水素原子、アルキル基、アルコキシ基、シ
クロアルキル基、アルコキシカルボニルアルキル基、ア
シルアルキル基、トリフルオロメチル基、ハロゲン原
子、シアノ基、ニトロ基、チアゾアゾリル基、水酸基、
アルコキシアルコキシ基、フェノキシ基、ベンジルオキ
シ基、アルケニル基、メチルチオ基、 (式中、RとR1はメチル基またはフェニル基を示
す。)、 (式中、R2とR3は水素原子またはメチル基を示し、R4は
水素原子またはクロロメタンスルホニルオキシ基を示
す。)、 または (式中、R5はフェニル基またはメチル置換ピペリジニル
基を示す。)を示す。nは1〜5の整数を示す。また、
Xnはベンゼン環上の2位と3位または3位と4位の相隣
る炭素原子を中心に酸素原子または窒素原子を含んでも
よい5員環または6員環を形成することもできる。)に
て示されるクロロメタンスルホン酸置換フェニルエステ
ル誘導体とを含有してなる。(Means for Solving Problems) The herbicidal composition of the present invention comprises a bench ocarb and a general formula. (In the formula, X is a hydrogen atom, an alkyl group, an alkoxy group, a cycloalkyl group, an alkoxycarbonylalkyl group, an acylalkyl group, a trifluoromethyl group, a halogen atom, a cyano group, a nitro group, a thiazoazolyl group, a hydroxyl group,
Alkoxyalkoxy group, phenoxy group, benzyloxy group, alkenyl group, methylthio group, (In the formula, R and R 1 represent a methyl group or a phenyl group.), (In the formula, R 2 and R 3 represent a hydrogen atom or a methyl group, and R 4 represents a hydrogen atom or a chloromethanesulfonyloxy group.), Or (In the formula, R 5 represents a phenyl group or a methyl-substituted piperidinyl group.) n shows the integer of 1-5. Also,
Xn can also form a 5-membered ring or 6-membered ring which may contain an oxygen atom or a nitrogen atom centering on the adjacent carbon atoms at the 2-position and 3-position or the 3-position and 4-position on the benzene ring. ) And a phenyl ester derivative substituted with chloromethanesulfonic acid.
次に本発明化合物を第1表に例示する。The compounds of the present invention are shown in Table 1 below.
一般式(I)で表わされる化合物は (1)一般式 (式中X及びnは前記と同一の意味を示す。)にて示さ
れるフェノール類とクロロメタンスルホニルハライド、
またはクロロメタンスルホン酸無水物とを脱ハロゲン化
水素剤、例えば苛性ソーダ、苛性カリ等の水酸化アルカ
リ、炭酸ナトリウム、炭酸カリウム、重炭酸ナトリウム
等の炭酸アルカリ、トリエチルアミン、ジメチルアニリ
ン、ピリジン等の第3級アミン等の有機または無機の塩
基の存在下または非存在下、アセトン、メチルエチルケ
トン、ジメチルホルムアミド、ジメチルスルホキシド、
テトラヒドロフラン、ベンゼン、トルエン、キシレン、
クロロベンゼン、ジクロロベンゼン、クロロホルム、四
塩化炭酸等の反応溶媒の存在下または非存在下−20℃〜
150℃の反応温度で反応を1〜20時間行うことによって
収率良く得られる。また、 (2)一般式 で示されるクロロメタンスルホニルオキシフェノールと 一般式 RY (式中、Rはアルキル基、アラルキル基、Yはハロゲン
原子を示す。)にて示されるハロゲン化物とを、脱ハロ
ゲン化水素剤、例えば苛性ソーダ、苛性カリ等の水酸化
アルカリ、炭酸ナトリウム、炭酸カリウム、重炭酸ナト
リウム等の炭酸アルカリ、トリエチルアミン、ジメチル
アニリン、ピリジン等の第3級アミン等の有機または無
機の塩基の存在下または非存在下、アセトン、メチルエ
チルケトン、ジメチルホルムアミド、ジメチルスルホキ
シド、テトラヒドロフラン、ベンゼン、トルエン、キシ
レン、クロロベンゼン、ジクロロメタン、クロロホル
ム、四塩化炭素等の反応溶媒の存在下−20℃〜150℃の
反応温度で反応を1〜20時間行えば 一般式 (式中、Rはアルキル基、アラルキル基を示す。)にて
示されるクロロメタンスルホン酸フェニルエステル誘導
体を得ることができる。 The compound represented by the general formula (I) includes (1) the general formula (Wherein X and n have the same meanings as described above), and a chloromethanesulfonyl halide,
Alternatively, a chloromethanesulfonic anhydride and a dehydrohalogenating agent such as alkali hydroxides such as caustic soda and caustic potash, alkali carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate, and tertiary tertiary amines such as triethylamine, dimethylaniline and pyridine. In the presence or absence of an organic or inorganic base such as amine, acetone, methyl ethyl ketone, dimethylformamide, dimethyl sulfoxide,
Tetrahydrofuran, benzene, toluene, xylene,
-20 ℃ ~ in the presence or absence of reaction solvent such as chlorobenzene, dichlorobenzene, chloroform, carbon tetrachloride
A good yield can be obtained by carrying out the reaction at a reaction temperature of 150 ° C. for 1 to 20 hours. Also, (2) general formula And a halide represented by the general formula RY (wherein R represents an alkyl group, an aralkyl group, and Y represents a halogen atom), and a dehydrohalogenating agent such as caustic soda, Acetone, in the presence or absence of alkali hydroxide such as caustic potash, alkali carbonate such as sodium carbonate, potassium carbonate and sodium bicarbonate, organic or inorganic base such as tertiary amine such as triethylamine, dimethylaniline and pyridine, If the reaction is carried out for 1 to 20 hours at a reaction temperature of -20 ° C to 150 ° C in the presence of a reaction solvent such as methyl ethyl ketone, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, benzene, toluene, xylene, chlorobenzene, dichloromethane, chloroform, carbon tetrachloride, etc. General formula (In the formula, R represents an alkyl group or an aralkyl group.) It is possible to obtain a chloromethanesulfonic acid phenyl ester derivative.
次に実施例を挙げて具体的な製造法を説明する。Next, a specific manufacturing method will be described with reference to examples.
実施例1 クロロメタンスルホン酸 4−イソプロピル
フェニル(化合物10)の製造 4−イソプロピルフェノール6.8g(0.05モル)をトルエ
ン80mlに溶かし、これにトリエチルアミン10g(0.1モ
ル)を加え0℃付近に冷却し攪拌下、クロロメタンスル
ホニルクロライド8.9g(0.06モル)を徐々に滴下した。
滴下後室温で1時間攪拌した。反応液を飽和食塩水で洗
浄し、さらに10%苛性ソーダ水溶液で洗浄、水洗後、無
水硫酸ナトリウムで乾燥した。次いで濾過し、濾液を濃
縮し得られた残渣を減圧蒸留した。クロロメタンスルホ
ン酸 4−イソプロフェニルを沸点126〜128℃/0.08mmH
gの留分に淡黄色液体として9.3g(収率75%)得た。Example 1 Preparation of 4-isopropylphenyl chloromethanesulfonate (Compound 10) 4-isopropylphenol (6.8 g, 0.05 mol) was dissolved in 80 ml of toluene, and 10 g (0.1 mol) of triethylamine was added thereto, followed by cooling to around 0 ° C and stirring. Below, 8.9 g (0.06 mol) of chloromethanesulfonyl chloride was gradually added dropwise.
After dropping, the mixture was stirred at room temperature for 1 hour. The reaction solution was washed with saturated brine, further washed with 10% aqueous sodium hydroxide solution, washed with water, and dried over anhydrous sodium sulfate. Then, the mixture was filtered, the filtrate was concentrated, and the obtained residue was distilled under reduced pressure. Chloromethanesulfonic acid 4-isoprophenyl boiling point 126-128 ℃ / 0.08mmH
A 9.3 g (75% yield) was obtained as a pale yellow liquid in the g fraction.
実施例2 クロロメタンスルホン酸 2,4−ジメチルフ
ェニル(化合物26)の製造 2,4−ジメチルフェノール10g(0.08モル)とトリエチル
アミン10.1g(0.1モル)を塩化メチレン100mlに溶かし
室温で攪拌下、クロロメタンスルホニルクロライド12.4
g(0.08モル)を徐々に滴下した。滴下後さらに30分間
攪拌を続けたのち、反応液を10%塩酸、10%苛性ソーダ
水溶液で洗浄し、さらに水洗した。有機層を無水硫酸ナ
トリウムで乾燥したのち、濾過し、濾液を濃縮した。得
られた残渣をヘキサン−酢酸エチル(2:1)を溶媒でカ
ラムクロマト精製を行いクロロメタンスルホン酸 2,4
−ジメチルフェニルを淡黄色透明液体として18.6g(収
率97%)得た(屈折率▲n20 D▼1.5250)。Example 2 Production of 2,4-dimethylphenyl chloromethanesulfonate (Compound 26) 2,4-Dimethylphenol 10 g (0.08 mol) and triethylamine 10.1 g (0.1 mol) were dissolved in 100 ml of methylene chloride and stirred at room temperature under stirring. Methanesulfonyl chloride 12.4
g (0.08 mol) was gradually added dropwise. After the dropwise addition, stirring was continued for another 30 minutes, and then the reaction solution was washed with 10% hydrochloric acid and 10% caustic soda aqueous solution, and further washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The obtained residue was purified by column chromatography with hexane-ethyl acetate (2: 1) as a solvent to obtain chloromethanesulfonic acid 2,4
18.6 g (yield 97%) of dimethylphenyl was obtained as a pale yellow transparent liquid (refractive index ▲ n 20 D ▼ 1.5250).
実施例3 クロロメタンスルホン酸 4−(1−エトキ
シカルボニル)イソブチルフェニルの製造(化合物39) 4−(1−エトキシカルボニル)イソブチルフェノール
10g(0.045モル)とトリエチルアミン7.1g(0.07モル)
を酢酸エチル200mlに溶かし室温で攪拌下クロロメタン
スルホニルクロライド7.8g(0.052モル)を徐々に滴下
した。滴下後さらに30分間攪拌を続けた。反応液を水洗
し、無水硫酸ナトリウムで乾燥した。次いで濾過し、濾
液を濃縮し得られた残渣を減圧蒸留し、クロロメタンス
ルホン酸 4−(1−エトキシカルボニル)イソブチル
フェニルを沸点156〜159℃/0.03mmHgの留分に淡黄色透
明粘調液体として13.7g(収率91%)を得た。Example 3 Preparation of 4- (1-ethoxycarbonyl) isobutylphenyl chloromethanesulfonate (Compound 39) 4- (1-Ethoxycarbonyl) isobutylphenol
10g (0.045mol) and triethylamine 7.1g (0.07mol)
Was dissolved in 200 ml of ethyl acetate, and 7.8 g (0.052 mol) of chloromethanesulfonyl chloride was gradually added dropwise at room temperature with stirring. After the dropping, stirring was continued for another 30 minutes. The reaction solution was washed with water and dried over anhydrous sodium sulfate. Then, the mixture was filtered, the filtrate was concentrated, and the resulting residue was distilled under reduced pressure to give 4- (1-ethoxycarbonyl) isobutylphenyl chloromethanesulfonate as a pale yellow transparent viscous liquid in a fraction having a boiling point of 156 to 159 ° C / 0.03 mmHg. As 13.7 g (yield 91%) was obtained.
実施例4 クロロメタンスルホン酸 4−フルオロフェ
ニル(化合部52)の製造 4−フルオロフェノール10g(0.09モル)とトリエチル
アミン14g(0.14モル)をトルエン100mlに溶かし0℃付
近に冷却し攪拌下クロロメタンスルホニルクロラド14g
(0.094モル)を徐々に滴下した。滴下後室温で1時間
攪拌を続けた。反応液を10%苛性ソーダ水溶液で洗浄、
さらに水洗し無水硫酸ナトリウムで乾燥した。次いで濾
過し、濾液を濃縮し得られた残渣を減圧蒸留し、クロロ
メタンスルホン酸 4−フルオロフェニルを沸点98〜10
1℃/0.09mmHgの留分に無色粘調液体として14.5g(収率7
3%)を得た。Example 4 Preparation of 4-fluorophenyl chloromethanesulfonate (Compound 52) 4-fluorophenol (10 g, 0.09 mol) and triethylamine (14 g, 0.14 mol) were dissolved in 100 ml of toluene, cooled to around 0 ° C. and stirred with chloromethanesulfonyl. Chlorad 14g
(0.094 mol) was gradually added dropwise. After the dropping, stirring was continued at room temperature for 1 hour. Wash the reaction solution with a 10% aqueous sodium hydroxide solution,
It was further washed with water and dried over anhydrous sodium sulfate. Then, the mixture was filtered, the filtrate was concentrated, and the resulting residue was distilled under reduced pressure to give 4-fluorophenyl chloromethanesulfonate having a boiling point of 98-10.
14.5g as a colorless viscous liquid in the fraction of 1 ℃ / 0.09mmHg (yield 7
3%) was obtained.
実施例5 クロロメタンスルホン酸 4−イソプロポキ
シフェニル(化合物73)の製造 4−クロロメタンスルホニルオキシフェノール3.3g(0.
015モル)をアセトニトリル50mlに溶かし炭酸カリウム
2.8g(0.02モル)を加え室温で攪拌下、ヨウ化イソプロ
ピル3.4g(0.02モル)を徐々に滴下した。滴下後浴温90
℃付近で5時間攪拌を行い放冷後、反応液を濾過し、濾
液を濃縮した。得られた残渣をベンゼン50mlに溶かし10
%苛性ソーダ水溶液で洗浄、さらに水洗後、無水硫酸ナ
トリウムで乾燥した。次いで濾過し、濾液を濃縮し得ら
れた残渣を減圧蒸留しクロロメタンスルホン酸 4−イ
ソプロポキシフェニルを沸点143〜145℃/0.19mmHgの留
分に微黄色液体として2.0g(収率50%)を得た。Example 5 Preparation of 4-isopropoxyphenyl chloromethanesulfonate (Compound 73) 4-chloromethanesulfonyloxyphenol 3.3 g (0.
015 mol) in 50 ml of acetonitrile and potassium carbonate
2.8 g (0.02 mol) was added and 3.4 g (0.02 mol) of isopropyl iodide was gradually added dropwise with stirring at room temperature. Bath temperature after dripping 90
After stirring for 5 hours at around ℃ and allowing to cool, the reaction solution was filtered and the filtrate was concentrated. Dissolve the obtained residue in 50 ml of benzene and
% Aqueous sodium hydroxide solution, washed with water, and dried over anhydrous sodium sulfate. Then, the filtrate was concentrated, and the obtained residue was distilled under reduced pressure to obtain 4-isopropoxyphenyl chloromethanesulfonate in a fraction having a boiling point of 143 to 145 ° C / 0.19 mmHg as a slightly yellow liquid (2.0 g, yield 50%). Got
実施例6 クロロメタンスルホン酸 3,4−メチレンジ
オキシフェニル(化合物83)の製造 3,4−メチレンジオキシフェノール5.5g(0.04モル)を
トルエン60mlに溶かし、これにトリエチルアミン8.1g
(0.08モル)を加え0℃付近に冷却し攪拌下クロロメタ
ンスルホニルクロライド8.9g(0.06モル)を徐々に滴下
した。滴下後2時間室温で攪拌した。反応液を水洗し、
無水硫酸ナトリウムで乾燥した。次いで濾過し、濾液を
濃縮し得られた残渣を減圧蒸留し、クロロメタンスルホ
ン酸 3,4−メチレンジオキシフェニルを沸点144〜146
℃/0.1mmHgの留分に黄色粘調液体として4.8(収率48
%)を得た。Example 6 Production of 3,4-methylenedioxyphenyl chloromethanesulfonate (Compound 83) 5.5 g (0.04 mol) of 3,4-methylenedioxyphenol was dissolved in 60 ml of toluene, and 8.1 g of triethylamine was added thereto.
(0.08 mol) was added, the mixture was cooled to around 0 ° C., and 8.9 g (0.06 mol) of chloromethanesulfonyl chloride was gradually added dropwise with stirring. After dropping, the mixture was stirred for 2 hours at room temperature. Wash the reaction solution with water,
It was dried over anhydrous sodium sulfate. Then, the mixture was filtered, the filtrate was concentrated, and the obtained residue was distilled under reduced pressure to give 3,4-methylenedioxyphenyl chloromethanesulfonate having a boiling point of 144 to 146.
4.8 (Yield 48% as a yellow viscous liquid in the fraction of ° C / 0.1 mmHg
%) Was obtained.
次に本発明の除草剤組成物はベンチオカーブと前記一般
式(I)で示される化合物の1種とを含有し、通常は担
体、界面活性剤、分散剤または補助剤等を配合して常法
により、例えば、粒剤、水和剤、乳剤、微粒剤または粉
剤に製剤する。好適な担体としては、例えば、タルク、
ベントナイト、クレー、カオリン、珪藻土、ホワイトカ
ーボン、バーミキュライト、消石灰、珪砂、硫安、尿素
等の固体担体、イソプロピルアルコール、キシレン、シ
クロヘキサノン等の液体担体等が挙げられる。Next, the herbicidal composition of the present invention contains bench iocarb and one of the compounds represented by the general formula (I), and is usually mixed with a carrier, a surfactant, a dispersant or an auxiliary agent and the like. To prepare, for example, granules, wettable powders, emulsions, fine granules or powders. Suitable carriers include, for example, talc,
Examples thereof include solid carriers such as bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate and urea, and liquid carriers such as isopropyl alcohol, xylene and cyclohexanone.
界面活性剤及び分散剤としては、例えば、アルコール硫
酸エステル塩、アルキルスルホン酸塩、リグニンスルホ
ン酸塩、ポリオキシエチレンアルキルアリールエーテ
ル、ポリオキシエチレンソルビタンモノアルキレート等
が挙げられる。Examples of surfactants and dispersants include alcohol sulfate ester salts, alkyl sulfonates, lignin sulfonates, polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monoalkylates, and the like.
これらの製剤を適宜な濃度に希釈して散布するか、また
は直接施用する。These formulations are diluted to an appropriate concentration and then sprayed or applied directly.
ベンチオカーブと前記一般式(I)で示されるクロロメ
タンスルホン酸置換フェニルエステル誘導体との配合比
は重量で前者10に対し後者が10〜0.1の範囲内であるこ
とが好ましい。It is preferable that the blend ratio of Benchiocarb to the chloromethanesulfonic acid-substituted phenyl ester derivative represented by the general formula (I) is in the range of 10 to 0.1 for the former and 10 for the latter by weight.
本発明の除草剤組成物はベンチオカーブに換算して10ア
ール当り50g〜1000gを施用する。The herbicidal composition of the present invention is applied in an amount of 50 g to 1000 g per 10 ares in terms of bench curve.
次に実施例を挙げて、具体的に説明する。下記実施例中
の%は重量百分率を意味する。Next, a specific description will be given with reference to examples. In the following examples,% means percentage by weight.
実施例8 (粒 剤) ベントナイト40%、クレー56.5%、アルキルベンゼンス
ルホン酸ナトリウム3%及びポリビニールアルコール0.
5%を適当量の水で練り合わせ、押し出し式造粒機にて
造粒後乾燥して14〜32メッシュに整粒した後、出来上が
った造粒体89.9%にベンチオカーブ10%と化合物(6)
0.1%を攪拌しながら吸着せしめて粒剤とする。Example 8 (Granule) Bentonite 40%, clay 56.5%, sodium alkylbenzene sulfonate 3% and polyvinyl alcohol
5% is kneaded with an appropriate amount of water, granulated by an extrusion-type granulator, dried, and then sized to 14 to 32 mesh, and then 89.9% of the finished granulated product, 10% of Bench-O-Curve and compound (6)
Adsorb 0.1% with stirring to make granules.
実施例9 (粒 剤) 実施例8構成物中の造粒体89.9%を89%とし化合物
(6)0.1%を1%とすることにより目的の配合比を有
する除草剤組成物を製造することが出来る。Example 9 (Granule) Example 8 A herbicidal composition having a target compounding ratio is prepared by using 89.9% of the granules in the composition as 89% and 0.1% of the compound (6) as 1%. Can be done.
実施例10 (粒 剤) 実施例8構成物中の造粒体89.9%を80%とした化合物
(6)0.1%を10%とすることにより目的の配合比を有
する除草剤組成物を製造することが出来る。Example 10 (Granule) Example 8 A herbicidal composition having a target compounding ratio is produced by adjusting 89.9% of granules in the composition to 80% and compound (6) 0.1% to 10%. You can
実施例11 (粒 剤) ベンチオカーブ10%、化合物(10)0.1%、リグニンス
ルホン酸ナトリウム2%、ホワイトカーボン5%、ベン
トナイト57.9%及びタルク25%を均一に粉砕混合して適
当量の水を加えて練り合わせ、押し出し式造粒機にて造
粒後乾燥して14〜32メッシュに整粒して製剤とした。Example 11 (Granule) Benchocarb 10%, Compound (10) 0.1%, Sodium ligninsulfonate 2%, White carbon 5%, Bentonite 57.9% and Talc 25% were uniformly pulverized and mixed, and an appropriate amount of water was added. The mixture was kneaded, kneaded, granulated by an extrusion-type granulator, dried and then sized to 14 to 32 mesh to give a preparation.
実施例12 (粒 剤) 実施例11構成物中の化合物(10)0.1%を1%とし、ベ
ントナイト57.9%を57%とすることにより目的の配合比
を有する除草剤組成物を製造することが出来る。Example 12 (Granule) Example 11 A herbicidal composition having a target compounding ratio can be produced by setting 0.1% of the compound (10) in the composition to 1% and 57.9% of bentonite to 57%. I can.
実施例13 (水和剤) ベンチオカーブ10%、化物(34)0.1%、ジナフチルメ
タンスルホン酸ナトリウム2%、ポリオキシエチレンア
ルキルフェニルエーテル1%及び珪藻土86.9%を混合
し、均一に粉砕して水和剤とする。Example 13 (Wettable powder) Benchocarb 10%, compound (34) 0.1%, sodium dinaphthylmethanesulfonate 2%, polyoxyethylene alkylphenyl ether 1% and diatomaceous earth 86.9% were mixed and uniformly pulverized with water. Use as a Japanese medicine.
実施例14 (水和剤) 実施例13構成物中の化合物(34)0.1%を1%とし、珪
藻土86.9%を86%とすることにより目的の配合比の有す
る除草剤組成物を製造することが出来る。Example 14 (Wettable powder) Example 13 To prepare a herbicidal composition having a target compounding ratio by setting 0.1% of the compound (34) in the composition to 1% and 86% of diatomaceous earth to 86%. Can be done.
実施例15 (水和剤) 実施例13構成物中の化合物(34)0.1%を10%とし、珪
藻土86.9%を77%とすることにより目的の配合比を有す
る除草剤組成物を製造することができる。Example 15 (Wettable powder) Example 13 To prepare a herbicidal composition having a target compounding ratio by setting 0.1% of the compound (34) in the composition to 10% and 86.9% of diatomaceous earth to 77%. You can
実施例16 (乳 剤) ベンチオカーブ30%、化合物(67)3%、シクロヘキサ
ノン20%、ホリオキシエチレンアルキルアリールエーテ
ル11%、アルキルベンゼンスルホン酸カルシウム4%及
びメチルナフタリン32%を均一に溶解して乳剤とした。Example 16 (Emulsion) Benchiocarb 30%, Compound (67) 3%, Cyclohexanone 20%, Forioxyethylene alkylaryl ether 11%, Calcium alkylbenzene sulfonate 4% and Methylnaphthalene 32% were uniformly dissolved to form an emulsion. did.
実施例17 (粉 剤) ベンチオカーブ3%、化合物(72)0.3%、珪藻土5%
及びクレー91.7%を均一に混合粉砕して粉剤とした。Example 17 (Powder) Bentocarb 3%, Compound (72) 0.3%, Diatomaceous earth 5%
And 91.7% of clay were uniformly mixed and pulverized to obtain a powder.
本発明の除草剤組成物は、稲の発芽時から5〜6葉期に
適用でき直播栽培、稚苗移植栽培、成苗移植栽培等に使
用できるものである。The herbicidal composition of the present invention can be applied from the germination of rice to the 5th to 6th leaf stage and can be used for direct seeding cultivation, seedling transplant cultivation, adult seedling transplant cultivation and the like.
(発明の効果) 本発明の前記一般式(I)で示される化合物は、未熟有
機物の多量施用等やその他の異常環境要因等により水田
が強還元状態となるような特殊な水田においてベンチオ
カーブによって稲に与えられる可能性のある有害作用を
防止することができる。(Effects of the Invention) The compound represented by the above general formula (I) of the present invention is used in a special paddy field in which a paddy field is in a strongly reduced state due to large-scale application of an immature organic substance or other abnormal environmental factors, and the rice is bentocurve It is possible to prevent the harmful effects that can be given to.
この有害作用を防ぐ物質はすでに提案されている(特開
昭58−105904号明細書、同58−116403号明細書及び同58
−128305号明細書)が、本発明の化合物はさらに極めて
低薬量で有害作用を防ぐことができる。このことは、環
境への影響がさらに小さくなるという意味からも有用性
のあるものである。また、本発明の化合物は土壌吸着性
もより向上しており、そのため、処理後の降雨等やかけ
流し等による田面水の流出が起った場面にもベンチオカ
ーブの有害作用を防ぐための効果が安定するという利点
を有している。また、本発明の化合物は土壌中で速やか
に分解され、かつ、土壌微生物への影響も極めて少ない
ことから、土壌微生物環境に及ぼす影響もなく安全な物
質である。Substances for preventing this harmful effect have already been proposed (JP-A-58-105904, JP-A-58-116403 and JP-A-58-116403).
However, the compounds of the present invention can prevent adverse effects at a very low dose. This is also useful in the sense that it has a smaller impact on the environment. Further, the compound of the present invention is further improved in soil adsorbability, therefore, the effect of preventing the harmful effect of bench eocurve even in the case where the outflow of rice field water due to rainfall after treatment or pouring over occurs. It has the advantage of being stable. In addition, the compound of the present invention is a safe substance with no effect on the soil microbial environment because it is rapidly decomposed in soil and has very little effect on soil microorganisms.
次に本発明の除草剤組成物の奏する効果を試験剤を挙げ
て説明する。Next, the effect of the herbicidal composition of the present invention will be described with reference to test agents.
試験例1 (水稲の薬害軽減試験) 砂質壌土の水田から採取した土を1/5000アール相当のワ
グネルポットに充填し、ポット当り24gの細断稲ワラを
混入して入水、代かきを行った。Test Example 1 (Pharmaceutical damage reduction test for paddy rice) Soil taken from paddy fields of sandy loam soil was filled in a Wagner pot equivalent to 1/5000 are, and 24 g of shredded rice straw was mixed into the pot for water entry and substituting. .
代かきの翌日に実施例13〜15に準して調整した水和剤の
所定量を水で希釈し湛水のまま散布処理した。The day after substituting, a predetermined amount of a wettable powder prepared according to Examples 13 to 15 was diluted with water and sprayed as it was.
その直後に土壌表層から3cmまでを電動ミキサーにより
混和し、処理後5日目に水稲稚苗(品種:金南風)を1
本1株とし、ポット当り2株ずつ移植した。ポットは、
1処理につき2反復とし処理後は夜間20〜22℃、昼間29
〜31℃のガラス温室で管理した。調査は移植後40日目に
株当りの草丈と薬害指数について行い、供試4株の平均
値を示した。Immediately after that, mix up to 3 cm from the soil surface layer with an electric mixer, and on the 5th day after the treatment, add 1 paddy rice seedling (variety: Kinnanfeng)
This strain was used as one strain, and two strains were transplanted per pot. The pot is
It is repeated twice for each treatment. After treatment, the temperature is 20-22 ℃ at night and 29 during daytime.
Controlled in a glass greenhouse at ~ 31 ° C. The survey was carried out 40 days after transplantation with respect to plant height and phytotoxicity index per strain, and the average value of the 4 tested strains was shown.
尚、比較薬剤として特開昭58−105904号公報記載の下記
を化合物を供試した。The following compounds described in JP-A-58-105904 were tested as comparative agents.
結果を第2表に示す。 The results are shown in Table 2.
薬害指数 0:正常(無処理区と同様) 1:生育抑制程度 10〜20% 2: 〃 21〜40% 3: 〃 41〜60% 4: 〃 61〜80% 5: 〃 81〜100% 尚、化合物8〜87単用区(0.8〜80g/アール)における
水稲の生育抑制は、化合物1〜7と同様、全く認められ
なかった。 Chemical damage index 0: Normal (similar to untreated plot) 1: Growth inhibition 10 to 20% 2: 〃 21 to 40% 3: 〃 41 to 60% 4: 〃 61 to 80% 5: 〃 81 to 100% In the same manner as in Compounds 1 to 7, no inhibition of growth of paddy rice was observed in Compounds 8 to 87 single-use plots (0.8 to 80 g / are).
試験例2 (除草効果試験) 試験例1と同一の方法と規模でワグネルポットに土を入
れ、代かきを行い、代かき翌日に表層の水を捨てて去り
土壌表面を露出させたところにタイヌビエとホタルイ及
びコナギの種子をそれぞれポット当り約20粒ずつ播種し
た。これらの種子は秋に採取したものを冷蔵庫内に湿潤
低温下で保存し休眠打破したものを使用した。ポットを
5日ほど温室内に放置し雑草の種子類が発芽したところ
を見計らって3cmの深さに再入水し、更に5日ほど置い
て雑草が1〜2葉期に達した頃に、実施例13〜15に準じ
て調整した水和剤の所定量を水で希釈し湛水のまま散布
処理した。Test Example 2 (Herbicidal effect test) In the same method and scale as in Test Example 1, soil was placed in a Wagner pot and scavenging was performed. On the day after scavenging, the surface water was discarded and the soil surface was exposed to expose the soil surface and firefly. Approximately 20 seeds of soybean and eel were sown in each pot. As these seeds, those collected in autumn were stored in a refrigerator under moist low temperature, and the dormancy was broken. Leave the pot in the greenhouse for about 5 days, re-immerse the seeds of the weeds at a depth of 3 cm after observing the germination of the seeds of the weeds, and leave it for about 5 days before the weeds reach the 1-2 leaf stage. A prescribed amount of the wettable powder prepared according to Examples 13 to 15 was diluted with water and sprayed as it was.
薬剤処理後30日目にポット当りの雑草生育抑制程度を下
記の基準に従い調査し、結果を第3表に指数で示す。Thirty days after the chemical treatment, the degree of inhibition of weed growth per pot was investigated according to the following criteria, and the results are shown in Table 3 as an index.
除草効果指数 0 :生育抑制程度 0%(無処理区と同様) 0.5: 〃 1〜10% 1 : 〃 11〜20% 1.5: 〃 21〜30% 2 : 〃 31〜40% 2.5: 〃 41〜50% 3 : 〃 51〜60% 3.5: 〃 61〜70% 4 : 〃 71〜80% 4.5: 〃 81〜90% 5 : 〃 91〜100% 第3表より明らかな通り、本発明化合物はベンチオカー
ブの除草効果には、全く影響を及ぼさなかった。なお、
化合物8〜87については単用区及びベンチオカーブ混用
区とも、化合物1〜7の示した結果と同様であった。Herbicidal effect index 0: Growth restraint 0% (similar to untreated area) 0.5: 〃 1-10% 1: 〃 11-20% 1.5: 〃 21-30% 2: 〃 31-40% 2.5: 〃 41〜 50% 3: 〃 51-60% 3.5: 〃 61-70% 4: 〃 71-80% 4.5: 〃 81-90% 5: 〃 91-100% As is clear from Table 3, the compounds of the present invention had no effect on the herbicidal effect of Benchiocarb. In addition,
Regarding Compounds 8 to 87, the results were the same as those of Compounds 1 to 7 in both the single-use group and the bench-ocarb mixed group.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 FI 技術表示箇所 (A01N 47/12 43:82) (72)発明者 川上 昇一 千葉県柏市布施新町1丁目1番7号 審査官 一色 由美子─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification number Reference number within the agency FI technical display location (A01N 47/12 43:82) (72) Inventor Shoichi Kawakami 1-1 Fuse Shinmachi, Kashiwa City, Chiba Prefecture No. 7 Examiner Yumiko Isshiki
Claims (1)
ルチオカルバマートと 一般式 (式中、Xは水素原子、アルキル基、アルコキシ基、シ
クロアルキル基、アルコキシカルボニルアルキル基、ア
シルアルキル基、トリフルオロメチル基、ハロゲン原
子、シアノ基、ニトロ基、チアジアゾリル基、水酸基、
アルコキシアルコキシ基、フェノキシ基、ベンジルオキ
シ基、アルケニル基、メチルチオ基、 (式中、RとR1はメチル基またはフェニル基を示
す。)、 (式中、R2とR3は水素原子またはメチル基を示し、R4は
水素原子またはクロロメタンスルホニルオキシ基を示
す。)、 または (式中、R5はフェニル基またはメチル置換ピペリジニル
基を示す。)を示す。nは1〜5の整数を示す。 また、Xnはベンゼン環上の2位と3位または3位と4位
の相隣る炭素原子を中心に酸素原子または窒素原子を含
んでもよい5員環または6員環を形成することもでき
る。)で表わされるクロロメタンスルホン酸置換フェニ
ルエステル誘導体とを含有することを特徴とする除草剤
組成物。1. S- (4-chlorobenzyl) N, N-diethylthiocarbamate and a compound of the general formula (In the formula, X is a hydrogen atom, an alkyl group, an alkoxy group, a cycloalkyl group, an alkoxycarbonylalkyl group, an acylalkyl group, a trifluoromethyl group, a halogen atom, a cyano group, a nitro group, a thiadiazolyl group, a hydroxyl group,
Alkoxyalkoxy group, phenoxy group, benzyloxy group, alkenyl group, methylthio group, (In the formula, R and R 1 represent a methyl group or a phenyl group.), (In the formula, R 2 and R 3 represent a hydrogen atom or a methyl group, and R 4 represents a hydrogen atom or a chloromethanesulfonyloxy group.), Or (In the formula, R 5 represents a phenyl group or a methyl-substituted piperidinyl group.) n shows the integer of 1-5. Further, Xn can also form a 5-membered ring or 6-membered ring which may contain an oxygen atom or a nitrogen atom centering on adjacent carbon atoms at the 2-position and 3-position or 3-position and 4-position on the benzene ring. . And a chloromethanesulfonic acid-substituted phenyl ester derivative represented by the formula (4).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61249196A JPH0761925B2 (en) | 1986-10-20 | 1986-10-20 | Herbicide composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61249196A JPH0761925B2 (en) | 1986-10-20 | 1986-10-20 | Herbicide composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63104903A JPS63104903A (en) | 1988-05-10 |
JPH0761925B2 true JPH0761925B2 (en) | 1995-07-05 |
Family
ID=17189332
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61249196A Expired - Lifetime JPH0761925B2 (en) | 1986-10-20 | 1986-10-20 | Herbicide composition |
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Country | Link |
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JP (1) | JPH0761925B2 (en) |
Cited By (1)
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KR101528375B1 (en) * | 2007-03-06 | 2015-06-11 | 우베 고산 가부시키가이샤 | tert-BUTYLPHENYL SULFONATE COMPOUND, NONAQUEOUS ELECTROLYTE SOLUTION FOR LITHIUM SECONDARY BATTERY USING THE SAME, AND LITHIUM SECONDARY BATTERY USING THE SAME |
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KR102674146B1 (en) * | 2020-04-21 | 2024-06-10 | 구미아이 가가쿠 고교 가부시키가이샤 | Methanogenesis inhibitor composition and method for inhibiting methanogenesis |
-
1986
- 1986-10-20 JP JP61249196A patent/JPH0761925B2/en not_active Expired - Lifetime
Cited By (1)
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---|---|---|---|---|
KR101528375B1 (en) * | 2007-03-06 | 2015-06-11 | 우베 고산 가부시키가이샤 | tert-BUTYLPHENYL SULFONATE COMPOUND, NONAQUEOUS ELECTROLYTE SOLUTION FOR LITHIUM SECONDARY BATTERY USING THE SAME, AND LITHIUM SECONDARY BATTERY USING THE SAME |
Also Published As
Publication number | Publication date |
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JPS63104903A (en) | 1988-05-10 |
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