JPH0247467B2 - - Google Patents
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- Publication number
- JPH0247467B2 JPH0247467B2 JP56212396A JP21239681A JPH0247467B2 JP H0247467 B2 JPH0247467 B2 JP H0247467B2 JP 56212396 A JP56212396 A JP 56212396A JP 21239681 A JP21239681 A JP 21239681A JP H0247467 B2 JPH0247467 B2 JP H0247467B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- atom
- formula
- tetrahydro
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
Description
本発明は一般式（）
〔式中、R1は炭素数１〜５のアルキル基、低級
アルケニル基を、R2は水素原子、メチル基、メ
トキシ基を、Ｘは塩素原子、臭素原子を表わす。〕
で示される２−フエニル−４，５，６，７−テト
ラヒドロ−2H−イソインドール誘導体、その製
造法およびそれを有効成分として含有する除草剤
に関するものである。
本発明者らは、ダイズ、ワタ、コムギ、トウモ
ロコシ、イネなどの重要作物を雑草の害から守
り、多くの収穫を維持するため選択性の高い優れ
た除草効力を有する除草剤の研究を続けてきた。
その結果、一般式（）で示される２−フエニル
−４，５，６，７−テトラヒドロ−2H−イソイ
ンドール誘導体が、畑地雑草の発芽後処理におい
てきわめて高い除草効力を示し、かつダイズに対
して高度な選択性を有することを見出すに至り、
本発明を完成した。
フエノキシ酢酸誘導体が強い除草効力を有する
ことは、数多くの特許および文献で周知の事実で
ある。しかしながら、これら既知のフエノキシ酢
酸誘導体の中には、フエニル核に４，５，６，７
−テトラヒドロイソインドール基を有するものは
無く、それに関する記載もまつたくなされていな
い。一方、２−フエニル−４，５，６，７−テト
ラヒドロ−2H−イソインドール誘導体が除草活
性を有することは、特公昭48−11940号公報に記
載されている。しかし、フエノキシ酢酸誘導体に
関してはなんら記載されていない。さらに後の実
施例からも明らかなように、本発明化合物は、従
来既知のフエノキシ酢酸誘導体、（例えば２，４，
５−Ｔ）および２−フエニル−４，５，６，７−
テトラヒドロ−2H−イソインドール誘導体（実
施例中の化合物(A)，(B)）に比べ優れた性質を有し
ている。本発明化合物は、畑地雑草に発芽前およ
び発芽後処理において高い除草効力を示し、ダイ
ズ、コムギ、トウモロコシに対しては害が少ない
優れた性質を持つている。特に本発明化合物を発
芽後処理で用いた場合、ダイズ畑の重要雑草であ
るアサガオ、イチビ、オナモミ、スベリヒユ、ア
メリカキンゴジカ、イヌホオズキなどの広葉雑草
に効力がきわめて高く、ダイズに対しては実施例
からも明らかなように害が少なく、高度なダイズ
選択性を示すことが特徴であり、ダイズ畑での使
用が期待される。また本発明化合物は、水田、各
種穀類、そ菜類、果樹園、芝生、牧草地、茶園、
桑園、ゴム園、森林地、非農耕地等の除草剤とし
ても有用である。
次に本発明化合物の合成法について述べる。本
発明化合物は次の反応式によつて合成される。
〔式中、R1、R2、Ｘは前述の通りである。〕
一般式（）で示されるテトラヒドロ−2H−
イソインドールを塩基、すなわち、炭酸ナトリウ
ム、炭酸カリウムなどの塩、水酸化ナトリウム、
ナトリウムアルコキサイドなどの金属化剤、３級
アミンなどの有幾塩基などの存在下でジメチルホ
ルムアミド、アセトニトリル、メチルエチルケト
ン、ジメチルスルホキサイド、リン酸ヘキサメチ
レントリアミドなどの溶媒中にて反応させ、金属
塩とした後、20℃〜100℃、好ましくは40℃〜80
℃で一般式（）
〔式中、Ｚは塩素原子、臭素原子、ヨウ素原子
を、R1、R2は前述のとおりである。〕
で示されるα−ハロカルボン酸エステルと反応さ
せることにより合成することができる。
次に実施例を示し、本発明化合物のより詳細な
説明を行なう。
実施例 １
２−（４−クロロ−２フルオロ−５−メトキシ
カルボニルフエニル）−４，５，６，７−テト
ラヒドロ−2H−イソインドール−１，３−ジ
オン〔化合物(1)〕
２−（４−クロロ−２−フルオロ−５−ヒドロ
キシフエニル）−４，５，６，７−テトラヒドロ
−2H−イソインドール−１，３−ジオン３ｇを
ジメチルホルムアミド100mlに溶かし、無水炭酸
カリウム0.8ｇを加えた。さらにブロム酢酸メチ
ルエステル1.8ｇを加え70℃〜80℃で３時間撹拌
した。放冷後、水を加えエーテルで抽出した。抽
出液は良く水洗し、無水炭酸マグネシウムで乾燥
した。乾燥剤を別し、減圧下濃縮した。残渣を
シリカゲルカラムクロマトグラフイーで精製して
1.3ｇの無色の結晶を得た。mp98〜99.5℃実施例
１と同様の方法で表−１に示した化合物を合成し
た。
The present invention is based on the general formula () [In the formula, R 1 represents an alkyl group or lower alkenyl group having 1 to 5 carbon atoms, R 2 represents a hydrogen atom, a methyl group, or a methoxy group, and X represents a chlorine atom or a bromine atom. ] The present invention relates to a 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by the following, a method for producing the same, and a herbicide containing the same as an active ingredient. The present inventors have continued research into herbicides with highly selective herbicidal efficacy in order to protect important crops such as soybean, cotton, wheat, corn, and rice from weed damage and maintain high yields. Ta.
As a result, the 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by the general formula () showed extremely high herbicidal efficacy in the post-emergence treatment of upland weeds, and It was discovered that it has a high degree of selectivity,
The invention has been completed. It is a well-known fact from numerous patents and literature that phenoxyacetic acid derivatives have strong herbicidal efficacy. However, some of these known phenoxyacetic acid derivatives have 4,5,6,7 on the phenyl nucleus.
- There is no one having a tetrahydroisoindole group, and no description regarding it has been made. On the other hand, it is described in Japanese Patent Publication No. 11940/1983 that 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivatives have herbicidal activity. However, nothing is described regarding phenoxyacetic acid derivatives. Further, as is clear from the later examples, the compounds of the present invention are based on conventionally known phenoxyacetic acid derivatives (e.g. 2,4,
5-T) and 2-phenyl-4,5,6,7-
It has superior properties compared to tetrahydro-2H-isoindole derivatives (compounds (A) and (B) in Examples). The compounds of the present invention exhibit high herbicidal efficacy against upland weeds in pre- and post-emergence treatments, and have excellent properties that cause little harm to soybeans, wheat, and corn. In particular, when the compound of the present invention is used in a post-emergence treatment, it is extremely effective against broad-leaved weeds such as morning glory, Japanese staghorn, Japanese snail, purslane, goldenrod, and physalis, which are important weeds in soybean fields. As is clear from the above, it is characterized by being less harmful and showing a high degree of soybean selectivity, and is expected to be used in soybean fields. The compound of the present invention can also be used in paddy fields, various grains, vegetables, orchards, lawns, pastures, tea gardens,
It is also useful as a herbicide for mulberry orchards, rubber plantations, forest land, non-agricultural land, etc. Next, a method for synthesizing the compound of the present invention will be described. The compound of the present invention is synthesized according to the following reaction formula. [In the formula, R 1 , R 2 and X are as described above.] ] Tetrahydro-2H- represented by the general formula ()
Isoindole with a base, i.e., salts such as sodium carbonate, potassium carbonate, sodium hydroxide,
React in a solvent such as dimethylformamide, acetonitrile, methyl ethyl ketone, dimethyl sulfoxide, or hexamethylene triamide phosphate in the presence of a metallizing agent such as sodium alkoxide, or a number of bases such as tertiary amine, After making metal salt, 20℃~100℃, preferably 40℃~80℃
General formula in °C () [In the formula, Z is a chlorine atom, a bromine atom, or an iodine atom, and R 1 and R 2 are as described above. ] It can be synthesized by reacting with an α-halocarboxylic acid ester shown below. Next, Examples will be shown to provide a more detailed explanation of the compounds of the present invention. Example 1 2-(4-chloro-2fluoro-5-methoxycarbonylphenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione [Compound (1)] 2-( Dissolve 3 g of (4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione in 100 ml of dimethylformamide, and add 0.8 g of anhydrous potassium carbonate. Ta. Further, 1.8 g of methyl bromoacetate was added and stirred at 70°C to 80°C for 3 hours. After cooling, water was added and extracted with ether. The extract was thoroughly washed with water and dried over anhydrous magnesium carbonate. The desiccant was removed and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography.
1.3 g of colorless crystals were obtained. The compounds shown in Table 1 were synthesized in the same manner as in Example 1 at mp98-99.5°C.
【表】
表−１に示した化合物のスペクトルデータを表
−２に示す。NMRは重クロロホルム中で、IRは
結晶はヌジヨール中で、それ以外は薄膜法で測定
した。[Table] The spectral data of the compounds shown in Table-1 are shown in Table-2. NMR was measured in deuterated chloroform, crystals were measured in nudyol, and other measurements were performed using the thin film method.
【表】【table】
【表】
本発明化合物を実際に使用する際には、農薬製
剤分野での常法に従がい乳剤、水和剤、懸濁剤、
粒剤、粉剤等の使いやすい形態に製剤して用いる
のが一般的である。この場合、それぞれの製剤中
の本発明化合物の含有量（重量比）は0.1〜90％、
好ましくは１〜80％である。これらの製剤品を調
製するにあたつて、固体担体としては例えば、カ
オリン、ペントナイト、タルク、けいそう土、ジ
ークライト、合成含水酸化珪素などがあげられ
る。また液体担体としては、キシレン、メチルナ
フタレンなどの芳香族炭化水素類、シクロヘキサ
ノン、イソホロンなどのケトン類、クロルベンゼ
ン、ジメチルホルムアミド、セロソルブ、エチレ
ングリコールおよび水などがあげられる。乳化、
分散、拡展などの目的に使用される界面活性剤と
しては、例えばポリオキシエチレンアルキルエー
テル、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スチルアリールエーテ
ル、ポリオキシエチレン脂肪酸エステル、ポリオ
キシエチレンソルビタン脂肪酸エステル、オキシ
エチレンオキシプロピレンポリマーなどの非イオ
ン界面活性剤およびアルキル硫酸エステル塩、ア
ルキルスルホン酸塩、ジアルキルスルホこはく酸
塩、アルキルアリールスルホン酸塩などの陰イオ
ン界面活性剤があげられ、これらを単独あるいは
混合して用いればよい。また必要に応じて、リグ
ニンスルホン酸塩、ポリビニルアルコールあるい
はメチルセルロースなどのセルロース誘導体を補
助剤として用いることができる。もちろん使用で
きる担体、界面活性剤などは、ここに示したもの
に限定されるものではない。
次に配合例をあげて具体的に説明するが配合割
合および担体を変更することができるのは言うま
でもない。なお各例中の部は重量部を示す。
配合例 １
化合物(1)80部、ポリオキシエチレンアルキルア
リールエーテル５部および合成含水酸化ケイ素
（ハイドレーテツドシンセテイツクシリコーンダ
イオキサイド）15部をよく粉砕混合して水和剤を
得る。
配合例 ２
化合物(2)10部、ポリオキシエチレンアルキルア
リールエーテル７部、アルキルアリールスルホン
酸塩３部およびシクロヘキサノン80部をよく混合
して乳剤を得る。
配合例 ３
化合物(1)１部、合成含水酸化ケイ素１部、リグ
ニンスルホン酸塩５部およびクレー92部をよく粉
砕混合し、水を加えてよく練り合わせた後造粒乾
燥して粒剤を得る。
配合例 ４
化合物(1)３部、リン酸イソプロピル0.5部、ク
レー66.5部およびタルク30部をよく粉砕混合して
粉剤を得る。
配合例 ５
化合物(2)20部を、ポリオキシエチレンソルビタ
ンモノオレートを３重量％を含む水溶液60部と混
合し、有効成分の粒度が3μ以下になるまで湿式
粉砕した上に分散安定剤としてアルギン酸ナトリ
ウムを３重量％含む水溶液20部を混合して懸濁製
剤100部を得る。
本発明化合物は発芽前または発芽後のいずれか
で用いる場合には施用量は相当広範囲の間で変え
られるが、通常は１アール当り、0.01〜100ｇ、
好ましくは0.1〜30ｇである。
また本発明化合物は除草剤としての効力向上を
目指し、他の除草剤との混合も可能であり、場合
によつては相乗効果を期待することもできる。さ
らに本発明化合物は必要に応じて殺虫剤、殺線虫
剤、殺菌剤、植物生長調節剤および肥料との混合
も可能である。
次に除草効力に係る実施例をあげ、本発明化合
物をさらに詳細に説明する。
なお実施例中の対照化合物を表−３に記す。
以下の各実施例における作物に対する薬害と雑
草に対する効力との評価はすべて以下に述べる基
準にしたがい、０から５までの整数による評価値
で表わした。
調査時点に枯れ残つた植物体の地上部の乾燥重
量をはかり、無処理区と比較したときの比率
（％）を計算する。作物と雑草とについて下表の
ような基準にもとづき薬害と除草効力を０から５
までの数字で評価した。[Table] When actually using the compound of the present invention, follow the conventional methods in the field of agricultural chemical formulations, such as emulsions, wettable powders, suspensions, etc.
It is generally formulated into easy-to-use forms such as granules and powders. In this case, the content (weight ratio) of the compound of the present invention in each formulation is 0.1 to 90%,
Preferably it is 1 to 80%. In preparing these pharmaceutical products, examples of solid carriers include kaolin, pentonite, talc, diatomaceous earth, ziecrite, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, ketones such as cyclohexanone and isophorone, chlorobenzene, dimethylformamide, cellosolve, ethylene glycol, and water. emulsification,
Examples of surfactants used for purposes such as dispersion and spreading include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene stylaryl ether, polyoxyethylene fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. , nonionic surfactants such as oxyethylene oxypropylene polymers, and anionic surfactants such as alkyl sulfates, alkyl sulfonates, dialkyl sulfosuccinates, and alkylaryl sulfonates. They may be used in combination. Furthermore, if necessary, a lignin sulfonate, polyvinyl alcohol, or a cellulose derivative such as methyl cellulose can be used as an adjuvant. Of course, the carriers, surfactants, etc. that can be used are not limited to those shown here. Next, a detailed explanation will be given by giving a formulation example, but it goes without saying that the formulation ratio and carrier can be changed. Note that parts in each example indicate parts by weight. Formulation Example 1 80 parts of compound (1), 5 parts of polyoxyethylene alkylaryl ether, and 15 parts of synthetic hydrated silicon oxide are thoroughly ground and mixed to obtain a wettable powder. Formulation Example 2 10 parts of compound (2), 7 parts of polyoxyethylene alkylaryl ether, 3 parts of alkylaryl sulfonate and 80 parts of cyclohexanone are thoroughly mixed to obtain an emulsion. Formulation Example 3 1 part of compound (1), 1 part of synthetic hydrated silicon oxide, 5 parts of lignin sulfonate and 92 parts of clay are thoroughly ground and mixed, water is added, the mixture is thoroughly kneaded, and then granulated and dried to obtain granules. . Formulation Example 4 3 parts of compound (1), 0.5 parts of isopropyl phosphate, 66.5 parts of clay and 30 parts of talc are thoroughly ground and mixed to obtain a powder. Formulation Example 5 20 parts of compound (2) was mixed with 60 parts of an aqueous solution containing 3% by weight of polyoxyethylene sorbitan monooleate, wet-pulverized until the particle size of the active ingredient was 3μ or less, and alginic acid was added as a dispersion stabilizer. Mix 20 parts of an aqueous solution containing 3% by weight of sodium to obtain 100 parts of a suspension preparation. When the compound of the present invention is used either before or after germination, the application rate can vary over a fairly wide range, but is usually 0.01 to 100 g per are;
Preferably it is 0.1-30g. Furthermore, the compound of the present invention can be mixed with other herbicides in order to improve its effectiveness as a herbicide, and in some cases, a synergistic effect can be expected. Furthermore, the compound of the present invention can be mixed with insecticides, nematicides, fungicides, plant growth regulators, and fertilizers, if necessary. Next, the compounds of the present invention will be explained in more detail by giving examples related to herbicidal efficacy. Note that the control compounds in the examples are shown in Table 3. All evaluations of chemical damage to crops and efficacy against weeds in the following Examples were expressed as evaluation values using integers from 0 to 5 in accordance with the criteria described below. The dry weight of the above-ground parts of the plants that remained withered at the time of the survey was measured, and the ratio (%) compared to the untreated area was calculated. The chemical damage and herbicidal efficacy of crops and weeds are evaluated from 0 to 5 based on the criteria shown in the table below.
Evaluated by numbers up to.
【表】
実施例 ２
畑状茎葉処理試験
面積33×23cm2のバツトに畑土壌を詰め、スベリ
ヒユ、マルバアサガオ、アメリカキンゴジカ、イ
チビ、イヌホオズキ、オナモミ、エノコログサお
よびダイズの種子を播種し、18日間生育させた。
この後、各化合物を乳剤に製剤し所定量を水で希
釈し、小型噴霧器で植物体上方から茎葉部全面に
均一に処理した。処理時の各雑草の生育状況は草
種により若干異なるが、概ね２〜４葉期で草丈は
２〜12cmであつた。
処理後、20日目に各化合物の除草効力および作
物薬害を調査した。その結果を表−４に示す。
なお、本試験は全期間を通じ温室内で行なつ
た。[Table] Example 2 Field-like stem and foliage treatment test Field soil was filled in a vat with an area of 33 x 23 cm2 , and seeds of purslane, common morning glory, red deer, Japanese commonweed, Japanese physalis, Japanese fir, Japanese foxtail, and soybean were sown for 18 days. I let it grow.
Thereafter, each compound was formulated into an emulsion, a predetermined amount was diluted with water, and the mixture was uniformly applied from the upper part of the plant to the entire stem and leaf area using a small sprayer. The growth status of each weed at the time of treatment differed slightly depending on the grass species, but it was generally in the 2-4 leaf stage and the plant height was 2-12 cm. On the 20th day after the treatment, the herbicidal efficacy and crop damage of each compound were investigated. The results are shown in Table 4. This test was conducted in a greenhouse throughout the entire period.
【表】【table】
【表】
実施例 ３
畑土壌処理試験
１／500aワグネルポツトに畑地土壌を詰め、
マルバアサガオ、イチビ、アオビユ、ダイズ、ト
ウモロコシの種子を播種し、１cmの厚さに覆土し
た。
このあと乳剤に製剤した所定量の化合物を小型
噴霧器で土壌表面に散布した。なお散布水量は10
／ａの割合とした。
このあと戸外で３週間経過させた後、各化合物
の除草効力および作物薬害を調査した。その結果
を表−５に示す。[Table] Example 3 Field soil treatment test Fill a 1/500a Wagner pot with field soil,
Seeds of morning glory, Japanese yam, Japanese apricot, soybean, and corn were sown and covered with soil to a thickness of 1 cm. Thereafter, a predetermined amount of the compound formulated into an emulsion was sprayed onto the soil surface using a small sprayer. The amount of water sprayed is 10
The ratio was set to /a. After 3 weeks in the open air, the herbicidal efficacy and crop damage of each compound were investigated. The results are shown in Table-5.
Claims (1)
アルケニル基を、R2は水素原子、メチル基、メ
トキシ基を、Ｘは塩素原子、臭素原子を表わす。〕 で示される２−フエニル−４，５，６，７−テト
ラヒドロ−2H−イソインドール誘導体。 ２ R2が水素原子である特許請求の範囲第１項
記載の２−フエニル−４，５，６，７−テトラヒ
ドロ−2H−イソインドール誘導体。 ３ 一般式 〔式中、Ｚは塩素原子、臭素原子、ヨウド原子
を、R1は炭素数１〜５のアルキル基、低級アル
ケニル基を、R2は水素原子、メチル基、メトキ
シ基を表わす。〕 で示されるα−ハロカルボン酸エステルと一般式 〔式中、Ｘは塩素原子、臭素原子を表わす。〕 で示されるテトラヒドロ−2H−イソインドール
とを塩基の存在下で反応させることを特徴とする
一般式 〔式中、R1は炭素数１〜５のアルキル基、低級
アルケニル基を、R2は水素原子、メチル基、メ
トキシ基を、Ｘは塩素原子、臭素原子を表わす。〕 で示される２−フエニル−４，５，６，７−テト
ラヒドロ−2H−イソインドール誘導体の製造法。 ４ 一般式 〔式中、R1は炭素数１〜５のアルキル基、低級
アルケニル基を、R2は水素原子、メチル基、メ
トキシ基を、Ｘは塩素原子、臭素原子を表わす。〕 で示される２−フエニル−４，５，６，７−テト
ラヒドロ−2H−イソインドール誘導体を有効成
分として含有することを特徴とする除草剤。 ５ 一般式 〔式中、R1は炭素数１〜５のアルキル基、低級
アルケニル基を、R2は水素原子、メチル基、メ
トキシ基を、Ｘは塩素原子、臭素原子を表わす。〕 で示される２−フエニル−４，５，６，７−テト
ラヒドロ−2H−イソインドール誘導体を有効成
分とする特許請求の範囲第４項に記載のダイズ用
除草剤。 ６ 一般式 〔式中、R1は炭素数１〜５のアルキル基、低級
アルケニル基を、R2は水素原子、メチル基、メ
トキシ基を、Ｘは塩素原子、臭素原子を表わす。〕 で示される２−フエニル−４，５，６，７−テト
ラヒドロ−2H−イソインドール誘導体を有効成
分とする特許請求の範囲第４項に記載のダイズ畑
用茎葉処理除草剤。[Claims] 1. General formula [In the formula, R 1 represents an alkyl group or lower alkenyl group having 1 to 5 carbon atoms, R 2 represents a hydrogen atom, a methyl group, or a methoxy group, and X represents a chlorine atom or a bromine atom. ] A 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by the following. The 2 -phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative according to claim 1, wherein 2 R 2 is a hydrogen atom. 3 General formula [In the formula, Z represents a chlorine atom, a bromine atom, or an iodine atom, R 1 represents an alkyl group having 1 to 5 carbon atoms or a lower alkenyl group, and R 2 represents a hydrogen atom, a methyl group, or a methoxy group. ] α-halocarboxylic acid ester shown by and the general formula [In the formula, X represents a chlorine atom or a bromine atom. ] A general formula characterized by reacting tetrahydro-2H-isoindole represented by in the presence of a base. [In the formula, R 1 represents an alkyl group or lower alkenyl group having 1 to 5 carbon atoms, R 2 represents a hydrogen atom, a methyl group, or a methoxy group, and X represents a chlorine atom or a bromine atom. ] A method for producing a 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative. 4 General formula [In the formula, R 1 represents an alkyl group or lower alkenyl group having 1 to 5 carbon atoms, R 2 represents a hydrogen atom, a methyl group, or a methoxy group, and X represents a chlorine atom or a bromine atom. ] A herbicide characterized by containing a 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by the following as an active ingredient. 5 General formula [In the formula, R 1 represents an alkyl group or lower alkenyl group having 1 to 5 carbon atoms, R 2 represents a hydrogen atom, a methyl group, or a methoxy group, and X represents a chlorine atom or a bromine atom. ] The soybean herbicide according to claim 4, which contains a 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by the following as an active ingredient. 6 General formula [In the formula, R 1 represents an alkyl group or lower alkenyl group having 1 to 5 carbon atoms, R 2 represents a hydrogen atom, a methyl group, or a methoxy group, and X represents a chlorine atom or a bromine atom. ] The foliage treatment herbicide for soybean fields according to claim 4, which contains a 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by the following as an active ingredient.
Priority Applications (35)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56212396A JPS58110566A (en) | 1981-12-25 | 1981-12-25 | 2-phenyl-4,5,6,7-tetrahydro-2h-isoindole derivative, its preparation and herbicide containing said derivative as active component |
| AU91035/82A AU557324B2 (en) | 1981-12-25 | 1982-12-01 | Tetrahydro phthalimide compounds |
| CA000417107A CA1181407A (en) | 1981-12-25 | 1982-12-06 | Tetrahydrophthalimide compounds, and their production and use |
| MX792382A MX155084A (en) | 1981-12-25 | 1982-12-07 | PROCEDURE FOR PRODUCING TETRAHYDROPHTHALIMIDE COMPOUNDS |
| ZA829023A ZA829023B (en) | 1981-12-25 | 1982-12-08 | Tetrahydrophthalimide compounds, and their production and use |
| KR1019820005661A KR840002811A (en) | 1981-12-25 | 1982-12-17 | Tetrahydrophthalimide Compounds |
| DE8585103131T DE3278993D1 (en) | 1981-12-25 | 1982-12-20 | Tetrahydrophthalimide compounds, their production and use |
| EP82111841A EP0083055B1 (en) | 1981-12-25 | 1982-12-20 | Tetrahydrophthalimide compounds, and their production and use |
| DE8282111841T DE3273387D1 (en) | 1981-12-25 | 1982-12-20 | Tetrahydrophthalimide compounds, and their production and use |
| EP85103131A EP0172306B1 (en) | 1981-12-25 | 1982-12-20 | Tetrahydrophthalimide compounds, their production and use |
| SK9544-82A SK278417B6 (en) | 1981-12-25 | 1982-12-22 | Tetrahydrophtalimide compounds, manufacturing process thereof and herbicidal agent on their base |
| HU824131A HU188525B (en) | 1981-12-25 | 1982-12-22 | Herbicidal preparations containing tetrahydrophthalimide derivatives and process for the production of the active substance |
| CS829544A CZ279697B6 (en) | 1981-12-25 | 1982-12-22 | Tetrahydrophthalimide compounds, process of their preparation and herbicidal agent based thereon |
| DK573482A DK154703C (en) | 1981-12-25 | 1982-12-23 | TETRAHYDROPHTHALIMIDE COMPOUNDS, HERBICIDE PREPARATIONS CONTAINING THESE AND USE THEREOF IN THE CONTROL OF WEEDS |
| ES518547A ES518547A0 (en) | 1981-12-25 | 1982-12-23 | A PROCEDURE FOR THE PREPARATION OF TETRAHYDROPHTHALIMIDE DERIVATIVES. |
| PL1982239711A PL134968B1 (en) | 1981-12-25 | 1982-12-23 | Herbicide and method of manufacture of novel derivatives of tetrahydrophtalimide |
| BR8207478A BR8207478A (en) | 1981-12-25 | 1982-12-23 | COMPOUND, PROCESS FOR THE PRODUCTION OF SAVED COMPOUND, HERBICIDE COMPOSITION, PROCESS FOR CONTROL OR EXTERMINATION OF WEEDS ON A PLOWED LAND, AND USE OF SUCH COMPOUND |
| UA3525700A UA7085A1 (en) | 1981-12-25 | 1982-12-24 | Method for obtaining tetrahydrophthalimide compounds |
| BG059040A BG41995A3 (en) | 1981-12-25 | 1982-12-24 | Herbicide composition and method for control of weeds |
| SU823525700A SU1366054A3 (en) | 1981-12-25 | 1982-12-24 | Method of obtaining tetrahydrophthalimide compounds |
| US06/473,755 US4670046A (en) | 1981-12-25 | 1983-03-09 | Tetrahydrophthalimide compounds, as post-emergence herbicides for use in soybean fields |
| ES524859A ES524859A0 (en) | 1981-12-25 | 1983-08-10 | A PROCEDURE FOR THE PREPARATION OF PHENYLTETRAHYDROPHTHALIMIDES |
| CA000452554A CA1186320A (en) | 1981-12-25 | 1984-04-19 | Tetrahydrophthalimide compounds, and their production and use |
| US06/887,970 US4770695A (en) | 1981-12-25 | 1986-07-21 | N-substituted phenyl tetrahydrophthalimide compounds, and their production and herbicidal use |
| US06/942,703 US4938795A (en) | 1981-12-25 | 1986-12-17 | Tetrahydrophthalimide compounds, and their production and use |
| MYPI87000999A MY101267A (en) | 1981-12-25 | 1987-07-14 | N-substituted phenyl tetrahydrophthalimide compounds, their production and herbicidal use |
| US07/102,617 US4881970A (en) | 1981-12-25 | 1987-09-30 | Tetrahydropthalimide compounds, and their production and use as herbicides |
| US07/102,615 US4826533A (en) | 1981-12-25 | 1987-09-30 | N-(substituted phenyl)-tetrahydrophthalimide compounds, and their production and herbicide use |
| DK237988A DK158262C (en) | 1981-12-25 | 1988-05-02 | INTERMEDIATES FOR THE PREPARATION OF HERBICIDE TETRAHYDROPHTHALIMIDE COMPOUNDS |
| MY90/88A MY8800090A (en) | 1981-12-25 | 1988-12-30 | Tetrahydropthalimide compounds and their production and use |
| LV930127A LV5089A3 (en) | 1981-12-25 | 1993-02-17 | Tetrahydrophthalimido Compound Pickup |
| LTRP479A LT2079B (en) | 1981-12-25 | 1993-04-07 | BACKGROUND OF THE PREFERRED EMBODIMENT OF TETRAHIDROFTALIMIDE |
| MD94-0030A MD56C2 (en) | 1981-12-25 | 1993-11-08 | Process for tetrahydrophthalimidic compounds obtaining |
| BG098553A BG61119B2 (en) | 1981-12-25 | 1994-02-24 | N-substituted phenyl tetrahydrophthalimide compounds and their production and herbicidal use |
| GEAP19941920A GEP19960465B (en) | 1981-12-25 | 1994-05-16 | Method of obtaining tetrahydrophthalimide compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56212396A JPS58110566A (en) | 1981-12-25 | 1981-12-25 | 2-phenyl-4,5,6,7-tetrahydro-2h-isoindole derivative, its preparation and herbicide containing said derivative as active component |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58110566A JPS58110566A (en) | 1983-07-01 |
| JPH0247467B2 true JPH0247467B2 (en) | 1990-10-19 |
Family
ID=16621888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56212396A Granted JPS58110566A (en) | 1981-12-25 | 1981-12-25 | 2-phenyl-4,5,6,7-tetrahydro-2h-isoindole derivative, its preparation and herbicide containing said derivative as active component |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS58110566A (en) |
| KR (1) | KR840002811A (en) |
| ZA (1) | ZA829023B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55139359A (en) * | 1979-04-13 | 1980-10-31 | Mitsubishi Chem Ind Ltd | Tetrahydrophthalimides, and herbicide containing compound as effective component |
| JPH0245621B2 (en) * | 1980-10-07 | 1990-10-11 | Mitsubishi Chem Ind | TETORAHIDOROFUTARUIMIDORUIOYOBIKOREOJUKOSEIBUNTOSURUJOSOZAI |
| JPS5813567A (en) * | 1981-06-29 | 1983-01-26 | ロ−ム・アンド・ハ−ス・コンパニ− | Substituted phthalimide compound and herbicidal composition |
-
1981
- 1981-12-25 JP JP56212396A patent/JPS58110566A/en active Granted
-
1982
- 1982-12-08 ZA ZA829023A patent/ZA829023B/en unknown
- 1982-12-17 KR KR1019820005661A patent/KR840002811A/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ZA829023B (en) | 1983-09-28 |
| JPS58110566A (en) | 1983-07-01 |
| KR840002811A (en) | 1984-07-21 |
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