JPS61236766A - O-substituted phenoxy heterocyclic compound, production thereof and herbicide containing said compound as active constituent - Google Patents
O-substituted phenoxy heterocyclic compound, production thereof and herbicide containing said compound as active constituentInfo
- Publication number
- JPS61236766A JPS61236766A JP60079727A JP7972785A JPS61236766A JP S61236766 A JPS61236766 A JP S61236766A JP 60079727 A JP60079727 A JP 60079727A JP 7972785 A JP7972785 A JP 7972785A JP S61236766 A JPS61236766 A JP S61236766A
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- Japan
- Prior art keywords
- formula
- compound
- heterocyclic compound
- compound expressed
- weeds
- Prior art date
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Abstract
Description
【発明の詳細な説明】
本発明は、一般式
〔式中、Ｒ１およびＶは同一または相異なり、水素原子
、ハロゲン原子、アルキル基またはハロアルキル基を表
わし、Ｘは式Ｃ４Ｈまたは窒素原子を表わし、Ｙはカル
ボニル基またはメチレン基を表わし、ｎは０または１を
表わす。〕
で示されるＯ−置換フェノキシ複素環化合物（以下、本
発明化合物と記す。）、その製造法およびそれを有効成
分とする除草剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula [wherein R1 and V are the same or different and represent a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group, and X represents a formula C4H or a nitrogen atom, Y represents a carbonyl group or a methylene group, and n represents 0 or 1. ] The present invention relates to an O-substituted phenoxy heterocyclic compound (hereinafter referred to as the compound of the present invention) represented by the formula (hereinafter referred to as the compound of the present invention), a method for producing the same, and a herbicide containing the same as an active ingredient.
ある種のフェノキシピリジン化合物、たとえば２．２’
−Ｃ１，２−フェニレンビス（オキシ）〕ビス〔５−ク
ロロピリジン〕等が除草剤の有効分として用いうろこと
は、ヨーロッパ特許公開第６１９１１号明細書に記載さ
れている。しかしながら、これらの化合物は除草剤の有
効成分として必ずしも常に充分なものであるとはいえな
い。Certain phenoxypyridine compounds, such as 2.2'
-C1,2-phenylenebis(oxy)]bis[5-chloropyridine] and the like are used as active ingredients in herbicides, as described in European Patent Publication No. 61911. However, these compounds cannot always be said to be sufficient as active ingredients in herbicides.
本発明化合物は畑地の茎葉処理および土壌処理において
、問題となる種々の雑草、たとえばソバカズラ、サナエ
タデ、スベリヒュ、ハコベ、シロザ、アオゲイトウ、ダ
イコン、ノハラガラシ、ナズナ、エビスグサ、イチビ、
フィールドパンジー、ヤエムグラ、アメリカアサガオ、
マルバアサガオ、オオイヌノフグリ、オナモミ等の広葉
ｍ草、ヒエ、イヌビエ、エノコログサ、メヒシバ、スズ
メノカタビラ、ノスズメノテッポウ、エンバク、カラス
ムギ、セイバンモロコシ等のイネ科雑草等に対して除草
効力を有し、しかもいくつかの本発明化合物はトウモロ
コシ、コムギ、イネ等の主要作物に対して問題となるよ
うな薬害を示さない。The compounds of the present invention can be used to treat various weeds that are problematic in the treatment of foliage and soil in upland areas, such as freckle grass, Japanese knotweed, purslane, chickweed, whiteweed, Japanese radish, Japanese radish, Japanese radish, shepherd's purse, Ebisu grass, Japanese radish, and other weeds.
Field pansy, Yaemugura, American morning glory,
It has a herbicidal effect on broad-leaved grasses such as mulva morning glory, oatweed, and Japanese sorghum, as well as grass weeds such as barnyard grass, Japanese barnyard grass, foxtail grass, black grass, grasshopper, oat, oat, and seiban sorghum. The compounds of the present invention do not cause any problematic phytotoxicity to major crops such as corn, wheat, and rice.
また、本発明化合物は水田の湛水処理において問題とな
る種々の雑草、たとえばタイヌビエ等のイネ科雑草、ア
ゼナ、キカシグサ、ミゾハコベ等の広葉雑草、タマガヤ
ツリ、ホタルイ、マツバイ等のカヤツリグサ科雑草、コ
ナギ等に対して除草効力を有し、しかもイネに対して問
題となるような薬害を示さない。In addition, the compound of the present invention can be applied to various weeds that are problematic in the waterlogging treatment of rice fields, such as grass weeds such as Japanese grasshopper, broad-leaved weeds such as azalea, japonica, and chickweed, cyperaceae weeds such as cypress, bulrush, and cypress, and cyperus weeds. It has a herbicidal effect on rice, and does not cause any harmful effects on rice.
本発明化合物は、一般式 〔式中、Ｒ”、Ｙおよびｎは前記と同じ意味を表わす。The compound of the present invention has the general formula [In the formula, R'', Y and n represent the same meanings as above.
〕
で示されるフェノール化合物と一般式
〔式中 Ｂｌおよび又は前記と同じ意味を表わし、Ｗは
ハロゲン原子を表わす。〕
で示される複素環化合物とを溶媒中、脱ハロゲン化水素
剤の存在下、室温から２５０℃、０．５時間〜４８時間
反応させることによって製造することができる。] A phenol compound represented by the general formula [wherein Bl and/or represents the same meaning as above, and W represents a halogen atom. ] It can be produced by reacting a heterocyclic compound represented by the following in a solvent in the presence of a dehydrohalogenating agent at room temperature to 250°C for 0.5 to 48 hours.
この反応に供される試剤の量は、フェノール化合物（ｔ
ｔ：］ １当量に対して、複素環化合物〔ｍ〕は０．９
〜１．１当量、脱ハロゲン化水素剤は１〜２０当量であ
る。The amount of reagents used in this reaction is the phenolic compound (t
t:] For 1 equivalent, the heterocyclic compound [m] is 0.9
~1.1 equivalents, and 1 to 20 equivalents of the dehydrohalogenating agent.
溶媒としては、ヘキサン、ヘプタン、リグロイン、石油
エーテル等の脂肪族炭化水素類、ベンゼン、トルエン、
キシレン等の芳香族炭化水素類、クロロホルム、四塩化
炭素、ジグ００２タン、クロロベンゼン、ジクロロベン
ゼン等のハロゲン化炭化水素類、−ジ
エチルエーテル、ジイソプロピルエーテル、ジオキサン
、テトラヒドロフラン、エチレングリコールジメチルエ
ーテル等のエーテル類、アセトン、メチルエチルケトン
、メチルイソブチルケトン、イソホロン、シクロヘキサ
ノン等のケトン類、アセトニトリル、イソブチロニトリ
ル等のニトリル類、ピリジン、トリエチルアミン、Ｎ、
Ｎ−ジエチルアニリン、トリブチルアミン、Ｎ−メチル
モルホリン等の第三級アミン類、ホルムアミド、Ｎ、Ｎ
−ジメチルホルムアミド、Ｎ、Ｎ−ジメチルアセトアミ
ド等の酸ナミド類、ジメチルスルホキシド、スルホラン
等の硫黄化合物、水等あるいはそれらの混合物が島げら
れる。As a solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, Zig002tan, chlorobenzene, dichlorobenzene, ethers such as -diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, Acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, ketones such as cyclohexanone, nitriles such as acetonitrile, isobutyronitrile, pyridine, triethylamine, N,
Tertiary amines such as N-diethylaniline, tributylamine, N-methylmorpholine, formamide, N,N
- Acidamides such as dimethylformamide and N,N-dimethylacetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, water, etc., or mixtures thereof are removed.
脱ハロゲン化水素剤としては、ピリジン、トリエチルア
ミン、Ｎ、Ｎ−ジエチルアニリン等の有機塩基、水酸化
ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カ
リウム、水素化ナトリウム等の無機塩基等があげられる
。Examples of the dehydrohalogenation agent include organic bases such as pyridine, triethylamine, and N,N-diethylaniline, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and sodium hydride.
反応終了後の反応液は、有機溶媒抽出および濃縮等の通
常の後処理を行い、必要ならば、クロマトグラフィー、
蒸留、再結晶等の操作によって精製することにより、目
的の本発明化合物を得ることができる。After the reaction is completed, the reaction solution is subjected to conventional post-treatments such as organic solvent extraction and concentration, and if necessary, chromatography,
The desired compound of the present invention can be obtained by purification by operations such as distillation and recrystallization.
次に本発明化合物の製造例を示す。Next, production examples of the compounds of the present invention will be shown.
製造例１ （本発明化合物（１）の製造）Ｏ−フェニル
フェノール１．７Ｎと２．５−ジクロロピリミジン１．
５１とをメチルエチルケトン８０−に溶解し、炭酸カリ
ウム１．５ｆを加えて８時間加流還流した。水２００−
を加え、クロロホルムで抽出した後溶媒を留去して５−
クロロ−２−（０−フェニルフェノキシ）ピリミジン２
．７ｆを得た。Production Example 1 (Production of Compound (1) of the Present Invention) O-phenylphenol 1.7N and 2.5-dichloropyrimidine 1.
51 was dissolved in 80% of methyl ethyl ketone, 1.5 f of potassium carbonate was added, and the mixture was heated and refluxed for 8 hours. water 200-
was added, extracted with chloroform, and the solvent was distilled off to obtain 5-
Chloro-2-(0-phenylphenoxy)pyrimidine 2
．． I got 7f.
製造例２ （本発明化合物（２）の製造）水素化ナトリ
ウム（純度６０％）０．６ｇおよびＤＭＦ８０−にＯ−
フェニルフェノール２、５５ ｆを加え、続いて２．５
−ジクロロピリジン２．２２Ｆを加えて２時間加熱還流
した。Production Example 2 (Production of Compound (2) of the Present Invention) 0.6 g of sodium hydride (purity 60%) and DMF80-
Add phenylphenol 2,55 f followed by 2,5
-Dichloropyridine 2.22F was added and heated under reflux for 2 hours.
水２００−を加え、クロロホルムで抽出した＝１）で精
製して５−クロロ−２−（Ｏ−フェニルフェノール）ピ
リジン２．５１を得た。200 g of water was added and the mixture was purified by extraction with chloroform (=1) to obtain 2.51 g of 5-chloro-2-(O-phenylphenol)pyridine.
製造例８ （本発明化合物（４）の製造）水素化ナトリ
ウム（純度６０％）０．６１およびＤＭ８０１１１０−
に、水冷下Ｏ−ヒドロキシベンゾフェノン２．９７ｇを
加えた後室温に戻し、２．５−ジクロロピリジン２．２
ｆを加えて１４０℃に８時間加熱した。氷２０〇−を加
えクロロホルムで抽出した後溶媒を留去−２−（ｏ−ベ
ンゾイルフェノキシ）ピリジン１．Ｏｆを得た。Production Example 8 (Production of Compound (4) of the Present Invention) Sodium hydride (purity 60%) 0.61 and DM801110-
To this, 2.97 g of O-hydroxybenzophenone was added under water cooling, and the temperature was then returned to room temperature.
f was added and heated to 140°C for 8 hours. After adding 200ml of ice and extracting with chloroform, the solvent was distilled off to remove 2-(o-benzoylphenoxy)pyridine.1. I got Of.
製造例４ （本発明化合物（８）の製造）Ｏ−ベンジル
フェノール１．２４Ｆと２，６−ジクロロピリミジン１
ｇとをメチルエチルケトン２６−に溶解し、炭酸カリウ
ム１ｇを加えて８時間加熱還流した。水２００−を加ｊ
えクロロホルムで抽出した後溶媒を留去し、
５−クロロ−２−（０−ベンジルフェノキシ）ピリミジ
ン１．８ｇを得た。Production Example 4 (Production of Compound (8) of the Invention) O-benzylphenol 1.24F and 2,6-dichloropyrimidine 1
g was dissolved in methyl ethyl ketone 26-, 1 g of potassium carbonate was added, and the mixture was heated under reflux for 8 hours. Add 200ml of water
After extraction with chloroform, the solvent was distilled off,
1.8 g of 5-chloro-2-(0-benzylphenoxy)pyrimidine was obtained.
このような製造法によって製造できる本発明化合物のい
くつかを、第１表に示す。Table 1 shows some of the compounds of the present invention that can be produced by such a production method.
＼、
＠１表
本発明化合物を除草剤の有効成分として用いる場合は、
通常固体担体、液体担体、界面活性剤、その他の製剤用
補助剤と混合して、乳剤、水和剤、懸濁剤、粒剤等に製
剤する。＼、＠Table 1 When using the compound of the present invention as an active ingredient of a herbicide,
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, suspensions, granules, etc.
これらの製剤には有効成分として本発明化合物を、重量
比で０．１〜９０％、好ましくは０．５〜８０％含有す
る。These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 90%, preferably 0.5 to 80%.
固体担体としては、カオリンクレー、アッタパルジャイ
トクレー、ベントナイト、酸性白土、パイロフィライト
、タルク、珪藻土、方解石、クル疋粉、尿素、硫酸アン
モニウム、合成含水酸化珪素等の微粉末あるいは粒状物
があげられ、液体担体としては、キシレン、メチルナフ
タレン等の芳香族炭化水素類、イソプロパツール、エチ
レングリコール、セロソルブ等のアルコール類、アセト
ン、シクロヘキサノン、イソホロン等のケトン類、大豆
油、綿実油等の植物油、ジメチルスルホキシド、アセト
ニトリル、水等があげられる。Examples of solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, turquoise powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, and dimethyl Examples include sulfoxide, acetonitrile, water, etc.
乳化、分散、湿展等のために用いられる界面活性剤とし
ては、アルキル硫酸エステル塩、アルキルアリールスル
ホン酸塩、ジアルキルスルホコハク酸塩、ポリオキシエ
チレンアルキルアリールエーテルリン酸エステル塩等の
陰イオン界ｍＦＳ性剤、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ポリオキシプロピレンブロックコ
ポリマー、ソルビタン脂肪酸エステル、ポリオキシエチ
レンソルビタン脂肪酸エステル等の非イオン界面活性剤
等があげられるう製剤用補助剤としては、リグニンスル
ホン酸塩、アルギン酸塩、ポリビニルアルコール、アラ
ビアガム、ＣＭＯ（カルボキシメチルセルロース）、Ｐ
ＡＰ（酸性リン酸イソプロピル）等があげられる。Surfactants used for emulsification, dispersion, wetting, etc. include anionic mFS such as alkyl sulfate salts, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate salts, etc. Adjuvants for formulations, such as nonionic surfactants such as sex agents, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, etc. Agents include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMO (carboxymethyl cellulose), P
Examples include AP (isopropyl acid phosphate).
次に製剤例を示す。なお、本発明化合物は第１表の化合
物番号で示す。部は重量部を示す。Examples of formulations are shown below. The compounds of the present invention are indicated by compound numbers in Table 1. Parts indicate parts by weight.
製剤例１
本発明化合物（１３５０部、リグニンスルホン酸カルシ
ウム８部、ラウリル硫酸ナトリウム２部および合成含水
酸化珪素４５部をよく粉砕混合して水和剤を得る。Formulation Example 1 The compound of the present invention (1350 parts, 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.
製剤例２
本発明化合物（１１） １０部、ポリオキシエチレンス
チリルフェニルエーテル１４部、ドデシルベンゼンスル
ホン酸カルシウム６部、キシレン８０部およびシクロヘ
キサノン４０部をよく混合して乳剤を得る。Formulation Example 2 10 parts of the compound of the present invention (11), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 80 parts of xylene and 40 parts of cyclohexanone are thoroughly mixed to obtain an emulsion.
製剤例８
本発明化合物（９）２部、合成含水酸化珪ｌ１部、リグ
ニンスルホン酸カルシウム２部、ベントナイト８０部お
よびカオリンクレー６５部をよく粉砕混合し、水を加え
てよく練り合せた後、造粒乾燥して粒剤を得る。Formulation Example 8 2 parts of the compound of the present invention (9), 1 part of synthetic hydrated silica oxide, 2 parts of calcium lignin sulfonate, 80 parts of bentonite and 65 parts of kaolin clay were thoroughly ground and mixed, and after adding water and kneading well, Granulate and dry to obtain granules.
製剤例４
本発明化合物（１Ｇ） ２５部、ポリオキシエチレンソ
ルビタンモノオレエート８部、ＣＭＣ８部および水６９
部を混合し、粒度が５ミクロン以下になるまで湿式粉砕
して懸濁剤を得る。Formulation Example 4 25 parts of the compound of the present invention (1G), 8 parts of polyoxyethylene sorbitan monooleate, 8 parts of CMC, and 69 parts of water
A suspension is obtained by mixing the parts and wet milling until the particle size is less than 5 microns.
このようにして製剤された本発明化合物は、雑草の出芽
前または出芽後に土壌処理、茎葉処理または湛水処理す
る。土壌処理には、上堰表面処理、土壌混和処理等があ
り、茎葉処理には、植物体の上方からの処理のほか、作
物に付着しないよう雑草に限って処理する局部処理等が
ある。The compound of the present invention thus formulated is treated with soil, foliage, or flooding before or after the emergence of weeds. Soil treatment includes upper weir surface treatment, soil mixing treatment, etc., and foliage treatment includes treatment from above the plant body, as well as local treatment that treats only weeds so that they do not attach to crops.
また、他の除草剤と混合して用いることにより、除草効
力の増強を期待できる。さらに、殺虫剤、殺ダニ剤、殺
線虫剤、殺菌剤、植物生長調節剤、肥料、土壌改良剤等
と混合して用いることもできる。Furthermore, by mixing it with other herbicides, it can be expected to increase the herbicidal efficacy. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like.
なお、本発明化合物は、水田、畑地、果樹園、牧草地、
芝生地、森林あるいは非農耕地等の除草剤の有効成分と
して用いることができる。The compound of the present invention can be used in rice fields, fields, orchards, pastures,
It can be used as an active ingredient in herbicides for lawns, forests, non-agricultural lands, etc.
本発明化合物を除草剤の有効成分として用いる場合、そ
お処理凰は、気象条件、製剤形態、処理時期、方法、場
所、対象雑草、対象作物等によっても異なるが、通常１
アールあたり０６５ｆ〜２００１．好ましくは１ｇ〜１
００Ｉであり、乳剤、水和剤、懸濁剤等は、通常その所
定量を１アールあたり１リツトル〜１０リツトルの（必
要ならば、展着剤等の補助剤を添加した）水で希釈して
処理し、粒剤は、なんら希釈することなくそのまま処理
する。When the compound of the present invention is used as an active ingredient of a herbicide, the amount of treatment required varies depending on weather conditions, formulation form, treatment time, method, location, target weeds, target crops, etc., but usually 1.
065f~2001. Preferably 1g to 1
00I, and emulsions, wettable powders, suspension agents, etc. are usually diluted in a specified amount with 1 to 10 liters of water per are (adding auxiliary agents such as spreading agents, if necessary). The granules are processed as is without any dilution.
展着剤としては、前記の界面活性剤のほか、ポリオキシ
エチレンＷＨＩＭ（エステル）、リグニンスルホン酸塩
、アビエチン酸塩、ジナフチルメタンジスルホン酸塩、
パラフィン等があげられる。In addition to the above-mentioned surfactants, the spreading agents include polyoxyethylene WHIM (ester), lignin sulfonate, abietate, dinaphthylmethane disulfonate,
Examples include paraffin.
次に、本発明化合物が除草剤の有効成分として有用であ
ることを試験例で示す。なお、本発明化合物は、第１表
の化合物番号で示し、比較対照に用いた化合物は第２表
の化合物記号で示す。Next, test examples demonstrate that the compounds of the present invention are useful as active ingredients of herbicides. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.
また、除草効力は、調査時の供試植物の出芽および生育
阻害の程度を肉［観察し、化合物を供試していない場合
と全くないしほとんど違いがないものをｒＯＪとし、供
試植物が枯死ないし生育が完全゛に阻害されているもの
を「５」として、０〜５０６段階に評価し、０，１．２
．８．４．５で示す。In addition, the herbicidal efficacy is measured by observing the degree of inhibition of budding and growth of the test plants at the time of the investigation, and rOJ is defined as having no or almost no difference from the case where no compound is tested. Rated on a scale of 0 to 506, with growth completely inhibited as 5, 0, 1.2
．． 8.4.5.
試験例１ 畑地茎葉処理試験
直径１０ｍ、深さ１０ｃｒ１１の円筒型プラスチックポ
ットに畑地土壌を詰め、ヒエ、エンバク、ダイコンおよ
びイチビを播種し、温室内で１０日間育成した。その後
、製剤例２に準じて供試化合物を乳剤にし、その所定量
を、１アールあたり１０リツトル相当の展着剤を含む水
で希釈し、小型噴霧器で植物体の上方から茎葉処理した
。処理後２０日間温室内で育成し、除草効力を調査した
。その結果を第８表に示す。Test Example 1 Upland Stem and Leaves Treatment Test A cylindrical plastic pot with a diameter of 10 m and a depth of 10 cr is filled with upland soil, and barnyard grass, oats, radish, and Japanese radish were sown and grown in a greenhouse for 10 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water containing a spreading agent equivalent to 10 liters per are, and the foliage was treated from above the plant using a small sprayer. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 8.
第 ８ 表
試験例２ 畑地茎葉処理試験
面１８８Ｘ２Ｂｃｄ、深さ１１副のバットに畑地土壌を
詰め、トウモロコシ、イチビ、エビスグサ、イヌビエ、
セイバンモロコシおよびエノコログサを播種し、１８日
間育成した。Table 8 Test Example 2 Field soil stem and leaf treatment test surface 188 x 2 Bcd, depth 11 vat filled with field soil,
Saban sorghum and hackberry were sown and grown for 18 days.
その後、製剤例２に準じて供試化合物を乳剤にし、その
所定量を、１アールあたり５リツトル相当の展着剤を含
む水で希釈し、小型噴霧器で植物体の上方から茎葉部全
面に均一に処理した。このとき雑草および作物の生育状
況は車種により異なるが、１〜４葉期で、草丈は２〜１
２ｃ１Ｎであった。処理２０日後に除草効力を調査した
。その結果を第４表に示す。Thereafter, make an emulsion of the test compound according to Formulation Example 2, dilute the specified amount with water containing a spreading agent equivalent to 5 liters per are, and use a small sprayer to spread it evenly over the entire stem and leaf area from above the plant body. processed. At this time, the growth conditions of weeds and crops vary depending on the vehicle type, but the growth status of weeds and crops is 1 to 4 leaves, and the plant height is 2 to 1.
It was 2c1N. The herbicidal efficacy was investigated 20 days after the treatment. The results are shown in Table 4.
なお、本試験は、全期間を通して温室で行った。This test was conducted in a greenhouse throughout the entire period.
第４表
試験例８ 畑地土壌処理試験
面積８８Ｘ２８ｄ、深さ１１３のバットに畑地土壌を詰
め、コムギ、イスビニ、ヤエムグラ、ハコベ、オオイヌ
ノフグリ、ノハラガラシ、サナエタデおよびソバカズラ
を播種し、１〜２αの厚さに覆土した。製剤例２に準じ
て供試化合物を乳剤にし、その所定量を、１アールあた
り１０リツトル相当の水で希釈し、小型噴霧器で土壌表
面に処理した。処理後２０Ｂ間温室で育成し、除草効力
を調資した。その結果を第５表に示す。Table 4 Test Example 8 Upland Soil Treatment Test A vat with an area of 88 x 28 d and a depth of 113 was filled with upland soil and sown with wheat, Isbini, Yaemula, chickweed, St. elegans, No. Covered with soil. The test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was applied to the soil surface using a small sprayer. After treatment, the plants were grown in a greenhouse for 20 hours to determine their herbicidal efficacy. The results are shown in Table 5.
１１５表
試験例４ 水田湛水処理試験
１１５００１ワグネルポツトに水田土壌を詰め、タイヌ
ビエ、広葉雑草（アゼナ、キカシグサ、ミゾハコベ）、
ホタルイの種子およびマツバイ越冬芽を１〜２３の深さ
に混ぜ込んだ。湛水して水田状態にした後、８葉期のイ
ネを移植し、温室内で育成した。５日後（タイヌビエの
０．５期）に、製剤例２に準じて供試化合物を乳剤にし
、その所定量を、１０ミリリツトルの水で希釈し水面に
処理し、その水深を４ｃＩＩ４とした。処理後２０日間
温室内で育成し、除草効力を調査した。その結果を第６
表に示す。なお、処理の翌日から２日間は、１日あたり
８１の水深に相当する量の漏水をおこなった。Table 115 Test Example 4 Paddy field flooding treatment test 115001 Wagner pots were filled with paddy soil, and the water was filled with Japanese millet, broad-leaved weeds (Azaena, Kikashigusa, Chickweed),
Firefly seeds and Pinella overwintering buds were mixed in at a depth of 1-23. After flooding the rice field to create a paddy field, rice at the 8-leaf stage was transplanted and grown in a greenhouse. After 5 days (the 0.5 stage of Japanese millet), the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the emulsion was diluted with 10 milliliters of water and applied to the water surface to a water depth of 4cII4. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The result is the 6th
Shown in the table. In addition, for two days from the day after the treatment, water leaked in an amount equivalent to 81 water depths per day.
Claims (3)
素原子、ハロゲン原子、アルキル基 またはハロアルキル基を表わし、Ｘは式 ＣＨまたは窒素原子を表わし、Ｙはカルボ ニル基またはメチレン基を表わし、ｎは０ または１を表わす。〕 で示されるｏ−置換フェノキシ複素環化合物。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 and R^2 are the same or different and represent a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group, and or represents a nitrogen atom, Y represents a carbonyl group or a methylene group, and n represents 0 or 1. ] An o-substituted phenoxy heterocyclic compound represented by the following.
またはハロアルキル基を表わし、 Ｙはカルボニル基またはメチレン基を表わ し、ｎは０または１を表わす。〕 で示されるフェノール化合物と一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＾１は水素原子、ハロゲン原子、アルキル基
またはハロアルキル基を表わし、 Ｘは式ＣＨまたは窒素原子を表わし、Ｗは ハロゲン原子を表わす。〕 で示される複素環化合物とを反応させることを特徴とす
る一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＾１、Ｒ＾２、Ｘ、Ｙおよびｎは前記と同じ
意味を表わす。〕 で示されるｏ−置換フェノキシ複素環化合物の製造法。(2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^2 represents a hydrogen atom, a halogen atom, an alkyl group, or a haloalkyl group, Y represents a carbonyl group or a methylene group, and n is 0 Or represents 1. ] There are phenol compounds and general formulas ▲ mathematical formulas, chemical formulas, tables, etc. , W represents a halogen atom. ] A general formula characterized by reacting with a heterocyclic compound represented by ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1, R^2, X, Y and n have the same meanings as above. represents. ] A method for producing an o-substituted phenoxy heterocyclic compound.
素原子、ハロゲン原子、アルキル基 を表わし、Ｘは式ＣＨまたは窒素原子を表わし、Ｙはカ
ルボニル基またはメチレン基を表わし、ｎは０または１
を表わす。〕 で示される。一置換フェノキシ複素環化合物を有効成分
として含有することを特徴とする除草剤。(3) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 and R^2 are the same or different and represent a hydrogen atom, a halogen atom, or an alkyl group, and , Y represents a carbonyl group or a methylene group, and n is 0 or 1
represents. ] It is indicated by. A herbicide characterized by containing a monosubstituted phenoxy heterocyclic compound as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60079727A JPS61236766A (en) | 1985-04-15 | 1985-04-15 | O-substituted phenoxy heterocyclic compound, production thereof and herbicide containing said compound as active constituent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60079727A JPS61236766A (en) | 1985-04-15 | 1985-04-15 | O-substituted phenoxy heterocyclic compound, production thereof and herbicide containing said compound as active constituent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61236766A true JPS61236766A (en) | 1986-10-22 |
Family
ID=13698232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60079727A Pending JPS61236766A (en) | 1985-04-15 | 1985-04-15 | O-substituted phenoxy heterocyclic compound, production thereof and herbicide containing said compound as active constituent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61236766A (en) |
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|---|---|---|---|---|
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| US8114882B2 (en) * | 2005-04-12 | 2012-02-14 | Merck Patent Gmbh | (1H-indol-7-yl)-(pyrimidin-2-ylamino)methanone derivatives and related compounds as IGF-R1 inhibitors for the treatment of cancer |
| WO2015089003A1 (en) | 2013-12-10 | 2015-06-18 | E. I. Du Pont De Nemours And Company | Herbicidal substituted pyrimidinyloxy benzene compounds |
| WO2015108779A1 (en) | 2014-01-16 | 2015-07-23 | E. I. Du Pont De Nemours And Company | Pyrimidinyloxy benzene derivatives as herbicides |
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-
1985
- 1985-04-15 JP JP60079727A patent/JPS61236766A/en active Pending
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| EP0467099A2 (en) * | 1990-07-05 | 1992-01-22 | Bayer Ag | Substituted acrylophenons |
| US8114882B2 (en) * | 2005-04-12 | 2012-02-14 | Merck Patent Gmbh | (1H-indol-7-yl)-(pyrimidin-2-ylamino)methanone derivatives and related compounds as IGF-R1 inhibitors for the treatment of cancer |
| WO2015089003A1 (en) | 2013-12-10 | 2015-06-18 | E. I. Du Pont De Nemours And Company | Herbicidal substituted pyrimidinyloxy benzene compounds |
| US9695155B2 (en) | 2013-12-10 | 2017-07-04 | E I Du Pont De Nemours And Company | Herbicidal substituted pyrimidinyloxy benzene compounds |
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| US11053204B2 (en) | 2015-06-05 | 2021-07-06 | Fmc Corporation | Pyrimidinyloxy benzene derivatives as herbicides |
| EP3943486A1 (en) * | 2015-06-05 | 2022-01-26 | FMC Corporation | 2-(phenyloxy or phenylthio)pyrimidine derivatives as herbicides |
| WO2016196606A1 (en) * | 2015-06-05 | 2016-12-08 | E I Du Pont De Nemours And Company | 2-(phenyloxy or phenylthio)pyrimidine derivatives as herbicides |
| TWI713530B (en) * | 2015-06-05 | 2020-12-21 | 美商艾佛艾姆希公司 | Pyrimidinyloxy benzene derivatives as herbicides |
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| US11427549B2 (en) | 2017-05-02 | 2022-08-30 | Fmc Corporation | Pyrimidinyloxy benzo-fused compounds as herbicides |
| CN113302187A (en) * | 2018-12-18 | 2021-08-24 | 拜耳公司 | Substituted pyridyloxybenzenes and their salts and their use as herbicides |
| WO2020126746A1 (en) | 2018-12-18 | 2020-06-25 | Bayer Aktiengesellschaft | Substituted pyridinyloxybenzenes and salts thereof and use thereof as herbicidal agents |
| JP2022513966A (en) * | 2018-12-18 | 2022-02-09 | バイエル・アクチエンゲゼルシヤフト | Substituted pyridinyloxybenzenes and their salts and their use as herbicides |
| EP3670505A1 (en) * | 2018-12-18 | 2020-06-24 | Bayer AG | Substituted pyridinyloxybenzenes, their salts and use of said compounds as herbicidal agents |
| WO2020193474A1 (en) | 2019-03-27 | 2020-10-01 | Bayer Aktiengesellschaft | Substituted 2-heteroarylaminobenzenes and the salts thereof and their use as herbicidal agents |
| WO2023186691A1 (en) | 2022-03-28 | 2023-10-05 | Bayer Aktiengesellschaft | Substituted 2-c-azines and salts thereof, and use thereof as herbicidal active substances |
| WO2023186690A1 (en) | 2022-03-28 | 2023-10-05 | Bayer Aktiengesellschaft | Substituted 2-aminoazines and salts thereof, and use thereof as herbicidal active substances |
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