JPS63264583A - Pyridyl-2-oxy-phenoxypropionic acid derivative - Google Patents
Pyridyl-2-oxy-phenoxypropionic acid derivativeInfo
- Publication number
- JPS63264583A JPS63264583A JP62097043A JP9704387A JPS63264583A JP S63264583 A JPS63264583 A JP S63264583A JP 62097043 A JP62097043 A JP 62097043A JP 9704387 A JP9704387 A JP 9704387A JP S63264583 A JPS63264583 A JP S63264583A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methyl
- oxy
- pyridyl
- phenoxypropionic acid
- 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.)
- Pending
Links
- 239000004009 herbicide Substances 0.000 claims abstract description 8
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 abstract description 15
- -1 oxadiazole halide Chemical class 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000007810 chemical reaction solvent Substances 0.000 abstract description 3
- FYDQQEVRVKAASZ-UHFFFAOYSA-N 5-(chloromethyl)-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(CCl)=N1 FYDQQEVRVKAASZ-UHFFFAOYSA-N 0.000 abstract description 2
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 abstract 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- 239000004094 surface-active agent Substances 0.000 description 4
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- 239000002253 acid Substances 0.000 description 3
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- 150000002148 esters Chemical class 0.000 description 3
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
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- 235000003351 Brassica cretica Nutrition 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
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- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 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
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 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
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規なピリジル−2−オキシ−フェノキシプロ
ピオン酸誘導体、その製造方法及び該化合物を有効成分
として含有する選択性除草剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel pyridyl-2-oxy-phenoxypropionic acid derivative, a method for producing the same, and a selective herbicide containing the compound as an active ingredient.
従来、多数のフェノキシプロピオン酸エステル誘導体が
除草活性を有することが報告されている。It has been reported that many phenoxypropionate derivatives have herbicidal activity.
例えば2− C4−(4−4リフルオロメチルフエノキ
シ)フェノキシフプロピオン酸メチルエステル、2−
C4−(2,4−ジクロロフェノキシ)フェノキシ〕プ
ロピオン酸メチルエステノベ2−[:4−(3,5−ジ
クロロ−2−ピリジルオキシ)フェノキシ〕プロピオン
酸メチルエステノペ2−C4−(5−)!Jフルオロメ
チルー2−ピリジルオキシ)フェノキシ〕プロピオン酸
ブチルエステル等が知られ、雑草駆除に用いられている
。しかしながら、これらの物質の作用性は常に十分なも
のとは限らない。For example, 2-C4-(4-4lifluoromethylphenoxy)phenoxyfupropionic acid methyl ester, 2-
C4-(2,4-dichlorophenoxy)phenoxy]methyl esternope propionate 2-[:4-(3,5-dichloro-2-pyridyloxy)phenoxy]methyl ester propionate 2-C4-(5- )! J fluoromethyl-2-pyridyloxy)phenoxypropionate butyl ester and the like are known and used for weed control. However, the effectiveness of these substances is not always sufficient.
ビート、大豆、綿、アルファルファ、ナタネ、馬鈴薯、
ヒマワリ、大根、白菜、キャベツ、トマト等の広葉作物
の栽培において、これらの有用作物を害することなく、
発芽前土壌処理、発芽後茎葉処理のいずれの処理方法で
も禾本科雑草を枯殺できる選択性除草剤に対する市場の
要望は、既に多数の除草剤が開発販売されている現在で
も依然として強いものがある。特に雑草発生後の茎葉処
理を行った場合、前記の従来のフェノキシプロピオン酸
エステル類は処理後効果発現までの所要日数が8日以上
もかかり、作物栽培者の不満が多く、この点の改良が強
く望まれていた。Beet, soybean, cotton, alfalfa, rapeseed, potato,
In the cultivation of broad-leaved crops such as sunflowers, radish, Chinese cabbage, cabbage, and tomatoes, without harming these useful crops,
There is still a strong market demand for a selective herbicide that can kill regular weeds using either pre-emergence soil treatment or post-emergence foliage treatment, even though many herbicides have already been developed and sold. . In particular, when foliage treatment is performed after weed emergence, the conventional phenoxypropionate esters described above take more than 8 days to achieve post-treatment effects, which has caused many dissatisfaction among crop growers. It was strongly desired.
本発明の目的は工業的に該化合物を得、更には市場の要
望にかなったなお一層改良された選択性除草剤を提供す
ることにある。The object of the present invention is to obtain said compounds industrially and to provide even more improved selective herbicides that meet the demands of the market.
〔問題点を解決するための手段及び作用〕本発明は一般
式(I)
(式中Xは水素原子または塩素原子を示し、R4は水素
原子またはメチル基を示し、R2は炭素原子1〜4個の
アルキル基を示す)
で表わされる新規なピリジル−2−オキシ−フェノキシ
、プロピオン酸誘導体(以下本発明化合物という)、そ
の製造法およびそれらを有効成分として含有する除草剤
を提供する。[Means and effects for solving the problems] The present invention is based on the general formula (I) (wherein, X represents a hydrogen atom or a chlorine atom, R4 represents a hydrogen atom or a methyl group, and R2 represents a carbon atom of 1 to 4 The present invention provides novel pyridyl-2-oxy-phenoxy, propionic acid derivatives (hereinafter referred to as the compounds of the present invention) represented by the following alkyl groups, a method for producing the same, and a herbicide containing the same as an active ingredient.
以下に本発明の詳細な説明する。The present invention will be explained in detail below.
本発明化合物は種々の方法で製造することができるが、
代表的な3種の製造方法を下記反応式で示す。但し式中
XSR,およびR2は前記と同じ意味を表わし、Hal
はハロゲン原子を表わす。The compound of the present invention can be produced by various methods, but
Three typical manufacturing methods are shown in the following reaction formulas. However, in the formula, XSR and R2 represent the same meanings as above, and Hal
represents a halogen atom.
これらの反応は反応溶媒の存在下あるいは不存在下に、
適当な塩基を用いることによって本発明化合物を得る。These reactions are carried out in the presence or absence of a reaction solvent.
The compounds of the present invention are obtained by using a suitable base.
反応溶媒としては、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
キサン等のニーfル類、クロロベンゼン、クロロホルム
、四塩化炭素、ジクロロエタン等のノ\ロゲン化炭化水
素類、トリエチルアミン、ピリジン、ジメチルアニリン
等の第3級アミンおよびアセトニトリル、ジメチルホル
ムアミド、ジメチルスルホキシド、りん酸へキサメチル
トリアミド等の極性溶媒等が用いられる。Examples of reaction solvents include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, and xylene, nitrogen compounds such as ethyl ether, tetrahydrofuran, and dioxane, and chlorobenzene, chloroform, carbon tetrachloride, and dichloroethane. Used are halogenated hydrocarbons, tertiary amines such as triethylamine, pyridine, and dimethylaniline, and polar solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide, and hexamethyltriamide phosphate.
塩基としては、トリエチルアミン、ピリジン、1.8−
ジアザビシクロ−(5,4,0) −7−ウンデセン、
ジメチルアニリン等の第3級アミン、水酸化す) IJ
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
炭酸アルカリ塩および水素化ナトリウムのような水素化
金属等が用いられる。反応は、通常約り℃〜約150℃
、好ましくは約り0℃〜約100℃の反応温度で進行し
、反応時間は、数分から約48v!tf間程度である。As a base, triethylamine, pyridine, 1.8-
diazabicyclo-(5,4,0)-7-undecene,
Tertiary amines such as dimethylaniline, hydroxide) IJ
alkali hydroxides such as aluminum, potassium hydroxide, alkaline earth hydroxides such as calcium hydroxide, alkali carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, and metal hydrides such as sodium hydride. etc. are used. The reaction usually takes place at a temperature of about 150°C to about 150°C.
, preferably at a reaction temperature of about 0° C. to about 100° C., and the reaction time ranges from several minutes to about 48 V! It is about between tf.
下記の第1表に本発明化合物の代表例を示すが、本発明
はこれらの化合物のみに限定されるものではない。Representative examples of the compounds of the present invention are shown in Table 1 below, but the present invention is not limited only to these compounds.
第1表
I Cji! HCH3n”1.5
2502 HCH,C)1. n25
1.50903 C,! C
H,C113口251.61505 Cj!
C)I3n−C3H,’n251.50866
C1l CH31−CJ、n251.
50407 C1l CL n
7C,)I、 n” 1.51088
0β [:L t−CJs 口25
1.50749 CJ2 HHn2
51.5255本発明の化合物を除草剤として使用する
場合、農薬補助剤を用いて農薬製剤上、一般に行われて
いる方法により、例えば乳剤、水和剤、水溶剤、油剤、
粉剤、粒剤等の製剤型態にして使用することができる。Table 1 I Cji! HCH3n”1.5
2502 HCH, C)1. n25
1.50903 C,! C
H, C113 mouth 251.61505 Cj!
C) I3n-C3H,'n251.50866
C1l CH31-CJ, n251.
50407 C1l CL n
7C,)I, n” 1.51088
0β [:L t-CJs mouth 25
1.50749 CJ2 HHn2
51.5255 When the compound of the present invention is used as a herbicide, it can be prepared by using a pesticide auxiliary and a method commonly used in pesticide formulations, such as emulsions, wettable powders, aqueous solutions, oil solutions, etc.
It can be used in the form of preparations such as powders and granules.
これら種々の製剤は実際の使用に際しては、そのまま使
用するか、または水で所定濃度に希釈して使用すること
ができる。In actual use, these various preparations can be used as they are or diluted with water to a predetermined concentration.
農薬補助剤の具体例としては、例えば希釈剤、界面活性
剤、安定剤、固着剤、エアーゾル用噴射剤、共力剤を挙
げることができる。希釈剤としての溶剤としては水、有
機溶剤、炭化水素類、ハロゲン化炭化水素類、アルコー
ル類、エーテル類、アルコールエーテル類、ケトン類、
エステル類、アミド類、スルホキシド類を挙げることが
できる。Specific examples of pesticide adjuvants include diluents, surfactants, stabilizers, sticking agents, aerosol propellants, and synergists. Solvents used as diluents include water, organic solvents, hydrocarbons, halogenated hydrocarbons, alcohols, ethers, alcohol ethers, ketones,
Examples include esters, amides, and sulfoxides.
また増量剤、固体担体としては無機質粉粒体、例えば消
石灰、マグネシウム石灰、石膏、炭酸カルシウム、砂土
、パーライト、軽石、珪藻土、アルミナ、ゼオライト、
粘度鉱物(滑石、バーミキュライト、カオリナイト)植
物性粉粒体(例えば澱粉、穀物、ブドウ糖等)、合成樹
脂粉粒体(例えばフェノール樹脂、炭素樹脂、塩化ビニ
ル樹脂)等を挙げることができる。界面活性剤としては
、アニオン界面活性剤(例えばアルキル硫酸エステル類
、アリールスルホン酸類、コハク酸塩酸、ポリエチレン
グリコール、アルキルアリールエーテル硫酸エステル塩
類)、カチオン界面活性剤(例えばアルキルアミン類、
ポリオキシエチレンアルキルアミン類)、非イオン界面
活性剤(例えばポリオキシエチサングリコールエーテル
類、ポリオキシエチレン−グリコールエステル類、多価
アルコールエステル類)、両性界面活性剤等を挙げるこ
とができる。その他、安定剤、固着剤、効力延長剤、分
散安定剤、共力剤等を挙げることができる。In addition, fillers and solid carriers include inorganic powder and granules such as slaked lime, magnesium lime, gypsum, calcium carbonate, sand, perlite, pumice, diatomaceous earth, alumina, zeolite,
Examples include clay minerals (talc, vermiculite, kaolinite), vegetable powder (for example, starch, grain, glucose, etc.), synthetic resin powder (for example, phenol resin, carbon resin, vinyl chloride resin), and the like. Examples of surfactants include anionic surfactants (e.g. alkyl sulfates, aryl sulfonic acids, succinic acid, polyethylene glycol, alkylaryl ether sulfate salts), cationic surfactants (e.g. alkyl amines,
Examples include polyoxyethylene alkyl amines), nonionic surfactants (for example, polyoxyethisane glycol ethers, polyoxyethylene glycol esters, polyhydric alcohol esters), and amphoteric surfactants. Other examples include stabilizers, fixing agents, efficacy extenders, dispersion stabilizers, and synergists.
活性成分として使用する本発明化合物の量は製剤の形態
及び施用する方法、目的、時期、雑草の発生状況等によ
って適当に変更することができる。The amount of the compound of the present invention used as an active ingredient can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, weed growth status, etc.
一般的に用いる場合は0.05〜10 kg/haであ
り、好ましくは0.1〜5kg/haである。When generally used, the amount is 0.05 to 10 kg/ha, preferably 0.1 to 5 kg/ha.
〔実施例〕
次に本発明を実施例をあげて具体的に説明するが、本発
明はこれらの例のみに限定されるものではない。[Example] Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited only to these Examples.
実施例1
(3−メチル−1,2,4−オキサジアゾ−5−イル)
メ′チル−2−C4−(3−クロロ−5−トリフロロメ
チル−2−ピリジルオキシ)−フェノキシフプロピオン
酸エステル(化合物No1)の合成
2− C4−(3−クロロ−5−トリフロロメチル−2
−ピリジルオキシ)−フェノキシ〕プロピオン酸1.8
3g、3−メチル−5−クロロメチル−1,2,4−オ
キサジアゾール0.8gおよび無水炭酸カリウム0.8
3 gをアセトニトリル50dに加え、撹拌しながら1
6時間還流した。反応混合液を冷却してから、無機物を
濾別したのち、アセトニトリルを留去した。残留物をカ
ラムクロマトグラフィー〔シリカゲル、ベンゼン/酢酸
エチル=lO/1 (V/V)で展開)で精製し、1
.23gの目的物(n” 1.5250)を得た。Example 1 (3-methyl-1,2,4-oxadiazol-5-yl)
Synthesis of methyl-2-C4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-phenoxyfupropionic acid ester (compound No. 1) 2-C4-(3-chloro-5-trifluoromethyl -2
-pyridyloxy)-phenoxy]propionic acid 1.8
3 g, 0.8 g of 3-methyl-5-chloromethyl-1,2,4-oxadiazole and 0.8 g of anhydrous potassium carbonate.
Add 3 g to 50 d of acetonitrile and add 1 while stirring.
It was refluxed for 6 hours. After the reaction mixture was cooled, inorganic substances were filtered off, and acetonitrile was distilled off. The residue was purified by column chromatography [silica gel, developed with benzene/ethyl acetate = lO/1 (V/V)], and 1
.. 23 g of target product (n'' 1.5250) was obtained.
口
実施例2
(3−メチル−1,2,4−オキサジアゾ−5−イル)
−1−エチル−2−(4−(3−クロロ−5−トリフロ
ロメチル−2−ピリジルオキシ)−フェノキシ)プロピ
オン酸エステル(化合物No。Example 2 (3-methyl-1,2,4-oxadiazol-5-yl)
-1-ethyl-2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-phenoxy)propionic ester (compound no.
3)の合成
2− C4−(3−クロロ−5−トリフロロメチル−2
−ピリジルオキシ)−フェノキシ〕フロピオン酸1.1
g、3−メチル−5−(α−クロロエチル)−1,2,
4−オキサジアゾール0.44 gおよび無水炭酸カリ
ウム0.42.gをアセトニトリル50m1に加え、撹
拌しながら16時間還流した。3) Synthesis of 2-C4-(3-chloro-5-trifluoromethyl-2
-pyridyloxy)-phenoxy]furopionic acid 1.1
g, 3-methyl-5-(α-chloroethyl)-1,2,
0.44 g of 4-oxadiazole and 0.42 g of anhydrous potassium carbonate. g was added to 50 ml of acetonitrile, and the mixture was refluxed for 16 hours while stirring.
反応混合液を冷却し、無機物を濾別したのち、アセトニ
トリルを留去した。残留物をカラムクロマトグラフィー
〔シリカゲル、ベンゼン/酢酸エチル=10/1 (
V/V)で展開〕で精製し0.8gの目的物(n251
.6150)を得た。After cooling the reaction mixture and filtering off inorganic substances, acetonitrile was distilled off. The residue was purified by column chromatography [silica gel, benzene/ethyl acetate = 10/1 (
V/V)] to obtain 0.8 g of the target product (n251
.. 6150) was obtained.
実施例3
乳剤の製造
本発明化合物Nα3を20部(部は重量部を示し、以下
同じ)、キシレン60部およびツルポール2806B
(商品名:東邦化学工業製界面活性剤)20部を均一に
撹拌、混合して乳剤とした。Example 3 Preparation of emulsion 20 parts of the present compound Nα3 (parts indicate parts by weight, the same applies hereinafter), 60 parts of xylene, and Tsurpol 2806B.
(Product name: Surfactant manufactured by Toho Chemical Industries) 20 parts were uniformly stirred and mixed to form an emulsion.
実施例4
水和剤の製造
ホワイトカーボン10部、ジ−クライト65部、ツルポ
ール5039 (商品名:東邦化学工業製界面活性剤)
5部および本発明化合物No、 5の20部を混合、粉
砕して水和剤とした。Example 4 Production of wettable powder White carbon 10 parts, Zeekrite 65 parts, Tsurupol 5039 (Product name: Surfactant manufactured by Toho Chemical Industries)
5 parts and 20 parts of the present compound No. 5 were mixed and ground to prepare a wettable powder.
実施例5
茎葉処理試験
22cmX16cmのプラスチックバットに畑土壌を詰
め、大豆、ビート、稲、小麦、トウモロコシ、エンバク
の種子を一定量播種し、その上にメヒシバ、ノビエ、タ
デ、ハコベ、シロザ等の雑草の種子を含む土壌を約l
amの厚さに覆土した。イネ科植物が3.0〜3.5葉
期になった時に所定の薬剤を均一に茎葉散布した。薬剤
処理後14日回心雑草の生育状態を観察し、第2表の結
果を得た。生育抑制程度の数値は5〜1の5段階(5は
完全枯死、1は全(影響なしを示す)に分けて表示した
。Example 5 Stalk and foliage treatment test Fill a 22cm x 16cm plastic vat with field soil, sow a certain amount of soybean, beet, rice, wheat, corn, and oat seeds, and then weeds such as crabgrass, wild grass, knotweed, chickweed, and white locust. Approximately 1 liter of soil containing seeds
It was covered with soil to a thickness of am. When the gramineous plants reached the 3.0 to 3.5 leaf stage, a prescribed chemical was uniformly sprayed on the foliage. The growth condition of the converted weeds was observed 14 days after the chemical treatment, and the results shown in Table 2 were obtained. The numerical value of the degree of growth inhibition was divided into five levels from 5 to 1 (5 indicates complete withering and 1 indicates no effect).
本発明化合物は豆類、綿、人参、馬鈴薯、ビート、カン
ラン、カラシ、カラシナ、落花生、大根、煙草、トマト
、キューリ等の栽培植物に対しては良好な選択性、即ち
通常の使用濃度では薬害を生ずることなく、雑草、特に
禾本科雑草、例えばタイヌビエ、メヒシバ、オヒシバ、
エノコログサ、野性エンバク、スズメノテッポウ、キン
エンコロ、シバムギ、カモジグサ、キョウギシバ、ジョ
ンソングラス等に対して発芽前土壌処理、発芽後茎葉゛
処理を行った場合、卓越した選択的防除効果を示す。The compound of the present invention has good selectivity for cultivated plants such as beans, cotton, carrot, potato, beet, citrus, mustard, mustard, peanut, radish, tobacco, tomato, cucumber, etc. Weeds, especially weeds of the genus family, such as Japanese millet, crabgrass, blackberry, etc.
When pre-emergence soil treatment and post-emergence foliage treatment are applied to foxtail grass, wild oat, sparrow gnome, goldenrod, grasshopper, staghorn grass, japonica grass, johnson grass, etc., excellent selective control effects are shown.
Claims (3)
素原子またはメチル基を示し、R_2は炭素原子1〜4
個のアルキル基を示す) で表わされることを特徴とするピリジル−2−オキシ−
フェノキシプロピオン酸誘導体。(1) General formula [I] ▲Mathematical formula, chemical formula, table, etc.▼[I] (In the formula, X represents a hydrogen atom or a chlorine atom, R_1 represents a hydrogen atom or a methyl group, and R_2 represents a carbon atom from 1 to 4
pyridyl-2-oxy-, which is represented by
Phenoxypropionic acid derivative.
るフェノキシプロピオン酸と、 一般式〔III〕 ▲数式、化学式、表等があります▼〔III〕 (式中R_1は水素原子またはメチル基を示し、R_2
は炭素原子1〜4個のアルキル基を示し、Halはハロ
ゲン原子を示す) で表わされるオキサジアゾールハロゲン化物とを反応さ
せることを特徴とする一般式〔 I 〕▲数式、化学式、
表等があります▼〔 I 〕 (式中X、R_1およびR_2は前記と同じ意味を表わ
す) で表わされるピリジル−2−オキシ−フェノキシプロピ
オン酸誘導体の製造法。(2) General formula [II] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] (In the formula, X represents a hydrogen atom or a chlorine atom) Phenoxypropionic acid and General formula [III] ▲ Mathematical formula, There are chemical formulas, tables, etc. ▼ [III] (In the formula, R_1 represents a hydrogen atom or a methyl group, and R_2
represents an alkyl group having 1 to 4 carbon atoms, and Hal represents a halogen atom) General formula [I]▲Mathematical formula, chemical formula,
There are tables etc. ▼ [I] (In the formula, X, R_1 and R_2 have the same meanings as above) A method for producing a pyridyl-2-oxy-phenoxypropionic acid derivative.
素原子またはメチル基を示し、R_2は炭素原子1〜4
個のアルキル基を示す) で表わされるピリジル−2−オキシ−フェノキシプロピ
オン酸誘導体を有効成分として含有することを特徴とす
る選択性除草剤。(3) General formula [I] ▲ Numerical formula, chemical formula, table, etc.▼ [II] (In the formula, X represents a hydrogen atom or a chlorine atom, R_1 represents a hydrogen atom or a methyl group, and R_2 represents a carbon atom from 1 to 4
A selective herbicide comprising, as an active ingredient, a pyridyl-2-oxy-phenoxypropionic acid derivative represented by:
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62097043A JPS63264583A (en) | 1987-04-20 | 1987-04-20 | Pyridyl-2-oxy-phenoxypropionic acid derivative |
NZ224297A NZ224297A (en) | 1987-04-20 | 1988-04-19 | Phenoxypropionic acid ester derivatives and herbicidal compositions |
BR8801855A BR8801855A (en) | 1987-04-20 | 1988-04-19 | HERBICIDE COMPOSITION UNDERSTANDING AS A ACTIVE INGREDIENT A PHENOXYPROPIONIC ACID DERIVATIVE DERIVATIVE AND PROCESS FOR THE PRODUCTION OF PHENOXYPROPIONIC ACER DERIVATIVES |
AU15007/88A AU614957B2 (en) | 1987-04-20 | 1988-04-20 | Phenoxypropionic acid ester derivative |
EP88303579A EP0288275B1 (en) | 1987-04-20 | 1988-04-20 | Phenoxypropionic acid derivatives for use as herbicides |
CN198888102313A CN88102313A (en) | 1987-04-20 | 1988-04-20 | Phenoxypropionic acid ester derivative |
DE8888303579T DE3877802T2 (en) | 1987-04-20 | 1988-04-20 | PHENOXYPROPIONIC ACID DERIVATIVES, APPLICABLE AS HERBICIDES. |
US07/184,052 US4948421A (en) | 1987-04-20 | 1988-04-20 | Phenoxypropionic acid ester derivatives as herbicides |
US07/535,518 US5207819A (en) | 1987-04-20 | 1990-06-11 | Phenoxypropionic acid ester derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62097043A JPS63264583A (en) | 1987-04-20 | 1987-04-20 | Pyridyl-2-oxy-phenoxypropionic acid derivative |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS63264583A true JPS63264583A (en) | 1988-11-01 |
Family
ID=14181570
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62097043A Pending JPS63264583A (en) | 1987-04-20 | 1987-04-20 | Pyridyl-2-oxy-phenoxypropionic acid derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63264583A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015097850A1 (en) * | 2013-12-27 | 2015-07-02 | アグロカネショウ株式会社 | Method for producing benzyl ester 2-aminonicotinate derivative |
-
1987
- 1987-04-20 JP JP62097043A patent/JPS63264583A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015097850A1 (en) * | 2013-12-27 | 2015-07-02 | アグロカネショウ株式会社 | Method for producing benzyl ester 2-aminonicotinate derivative |
JPWO2015097850A1 (en) * | 2013-12-27 | 2017-03-23 | アグロカネショウ株式会社 | Method for producing 2-aminonicotinic acid benzyl ester derivative |
US9695124B2 (en) | 2013-12-27 | 2017-07-04 | Agro-Kanesho Co., Ltd. | Method of producing 2-aminonicotinic acid benzyl ester derivatives |
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