CN104649995B - A kind of 6 chloro benzo oxazole epoxide phenoxy propionic acid allyl ester type compound and its application as herbicide - Google Patents
A kind of 6 chloro benzo oxazole epoxide phenoxy propionic acid allyl ester type compound and its application as herbicide Download PDFInfo
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- CN104649995B CN104649995B CN201310606528.9A CN201310606528A CN104649995B CN 104649995 B CN104649995 B CN 104649995B CN 201310606528 A CN201310606528 A CN 201310606528A CN 104649995 B CN104649995 B CN 104649995B
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- propionic acid
- herbicide
- phenoxy propionic
- acid allyl
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- 0 CC(C(O*)=O)Oc(cc1)ccc1Oc1nc(ccc(Cl)c2)c2[o]1 Chemical compound CC(C(O*)=O)Oc(cc1)ccc1Oc1nc(ccc(Cl)c2)c2[o]1 0.000 description 2
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N CC(C(O)=O)Oc(cc1)ccc1Oc1nc(ccc(Cl)c2)c2[o]1 Chemical compound CC(C(O)=O)Oc(cc1)ccc1Oc1nc(ccc(Cl)c2)c2[o]1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention discloses a kind of 6 chloro benzo oxazole epoxide phenoxy propionic acid allyl esters and its application as herbicide, the compound such as formula（I）It is shown：Wherein：R1、R2It is respectively selected from hydrogen or methyl；R3、R4It is respectively selected from hydrogen, halogen or methyl；Double bond is configured as E or Z configurations, or E and Z configuration different proportions mixture；Mark * asymmetric carbon atom be R or S configurations, or R and S different proportions mixture.Compound of the invention not only has excellent activity of weeding, and to crop safety.
Description
Technical field
The invention belongs to herbicide field.Specifically a kind of 6- chloro benzos oxazole epoxide phenoxy propionic acid allyl esters
Compound and its application as herbicide.
Background technology
Due to weed population succession, transition and it is drug-fast to chemical pesticide generation and develop rapidly, people's opposite
The continuous reinforcement of state environmental protection consciousness, on chemical pesticide pollution, the understanding that is influenceed on non-target organism of agricultural chemicals and in agricultural chemicals
The attention of home to return to problem is improved constantly in ecological environment.With the gradually decreasing of world's cultivated area, the continuous growth of population and
Increase to grain demand amount, forces people to develop agriculture production technology, improvement rapidly and improves cropping system, and need constantly hair
Bright new and improved herbicides compounds and composition.
US4130413A reports some 5- chloro benzo oxazole epoxide phenoxy propionic acid allyls ester type compounds can be used as removing
Careless agent, such as No. 131 compound K C therein：
6- chloro benzo oxazole epoxide phenoxy propionic acid allyl ester type compounds as representative of the present invention are not disclosed.
The content of the invention
It is an object of the invention to provide a kind of structure novelty and to the 6- chloro benzo oxazole epoxide benzene oxygen third of crop safety
Allyl propionate class compound and its application as herbicide.
Technical scheme is as follows：
The invention provides a kind of 6- chloro benzos oxazole epoxide phenoxy propionic acid allyl ester type compound, as shown in formula I：
In formula：
R1、R2It is respectively selected from hydrogen or methyl；
R3、R4It is respectively selected from hydrogen, halogen or methyl；
Double bond is configured as E or Z configurations, or E and Z configuration different proportions mixture；
Mark * asymmetric carbon atom be R or S configurations, or R and S different proportions mixture.
Currently preferred structural formula of compound is as follows：
R1、R3And R4It is respectively selected from hydrogen；
R2Selected from hydrogen or methyl；
Mark * asymmetric carbon atom be R or S configurations, or R and S different proportions mixture.
The structural formula of compound that the present invention is more highly preferred to is as follows：
R1、R2、R3And R4It is respectively selected from hydrogen；
The asymmetric carbon atom for marking * is R configurations.
General formula compound I of the invention can be prepared by the following method：
By raw material II（II-a：R=Et, can be bought by market；II-b：R=Me, refers to US4130413A and is obtained）It is dissolved in suitable
In suitable solvent, and it is added in alkaline aqueous solution, temperature is -10 DEG C and is reacted 0.5-48 hours between boiling point, then through hydrochloric acid
Or sulfuric acid acidifying, it is compound III that intermediate acid is obtained.Suitable solvent be selected from chloroform, dichloromethane, carbon tetrachloride, just oneself
Alkane, benzene, toluene, ethyl acetate, methyl alcohol, ethanol, THF or dioxane etc.；Suitable alkali be selected from NaOH, potassium hydroxide,
Sodium carbonate, potassium carbonate or sodium acid carbonate etc..
Intermediate acid III is dissolved in suitable solvent, such as chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene,
In ethyl acetate, THF, DMF or dioxane etc., and alkaloids are added, such as triethylamine, pyridine, NaOH, hydroxide
Potassium, sodium carbonate, potassium carbonate, sodium acid carbonate etc., temperature are -10 DEG C and are reacted 0.5-48 hours between boiling point, adds corresponding
Alkenyl halide, is -10 DEG C and is reacted 0.5-48 hours between boiling point then at temperature, and object I is obtained.
Table 1：The compounds of this invention and physical property of the part as shown in formula I
Note：-- expression is not surveyed
Part of compounds1H NMR(300MHz,CDCl3) data are as follows：
Compound 1：7.70–7.17(m,5H),6.96(d,2H),5.90(ddd,1H),5.51–5.15(m,2H),4.95–
4.49(m,3H),1.64(dd,3H)。
Compound 3：7.60–7.18(m,5H),7.09–6.86(m,2H),6.04(t,1H),4.87–4.62(m,3H),
1.65(d,3H)。
Compound 5：7.54–7.20(m,5H),6.95(d,2H),6.05(dd,1H),5.14(dd,2H),4.65(m,
1H),1.61(d,3H),1.53(d,6H)。
Compound of Formula I of the invention has activity of weeding, can be used to agriculturally prevent and treat various weeds.Such as：Make in after seedling
With can effectively control monocotyledon weed.With the compound phase ratio disclosed in prior art, 6- chloro benzos oxazole oxygen of the invention
Base phenoxy propionic acid allyl ester compound not only has excellent activity of weeding, and to rice safety.
Present invention additionally comprises the Herbicidal combinations with compound of Formula I as active component.Activearm in the Herbicidal combinations
The weight percentage for dividing is 1-99%.Also include agriculturally acceptable carrier in the Herbicidal combinations.
Herbicidal combinations of the invention can be applied in the form of several formulations.Generally compound of the invention is dissolved or divided
Dissipate more readily dispersible when being configured to preparation to be used as herbicide in carrier.For example：These chemicals can be made into
Wettable powder or missible oil etc..Therefore, in these compositions, a kind of liquid or solid carrier is at least added, and generally need
Add appropriate surfactant.
Present invention also offers the implementation of controlling weeds, the method is included the weeding of the invention of herbicidally effective amount
Composition is imposed on the weeds or the place of the weed growth or the surface of its somatomedin.More suitable effective dose is
1 gram to 1000 grams of per hectare, preferably effective dose are 10 grams to 500 grams of per hectare.For some applications, can be removed of the invention
One or more other herbicide is added in careless composition, additional advantage and effect thus can be produced.
Compound of the invention both can be used alone can also be with other known insecticide, bactericide, plant growth
Conditioning agent or fertilizer etc. are mixed together.
It should be appreciated that, in scope defined by the claims of the present invention, various conversion and change can be carried out.
Specific embodiment
The following example and raw test result can be used to further illustrate the present invention, but be not intended to limit the present invention.
Synthesis example
The synthesis of example 1, compound 1：
（1）The synthesis of intermediate (R)-III
To adding fenoxapropPethyl in 500 milliliters of reaction bulbs（36.18 grams, 100 mMs, purchased from Jiangsu Feng Shanji
Co., Ltd of group, the asymmetric carbon atom for marking * is R configurations）With 80 milliliters of tetrahydrofurans, stirring to complete molten, the lower addition hydrogen-oxygen of cooling
Change sodium（4.17 grams, 100 mMs, content>96%）And water（100 milliliters）The solution of formation, is warmed to room temperature stirring reaction 5 naturally
Hour, stop reaction, 100 milliliters of ethyl acetate extractions are added, water is acidified with concentrated hydrochloric acid, and filtering, filtration cakes torrefaction obtains 25.00 grams
Intermediate acid (R)-III, white solid, m.p.157-158 DEG C, yield 75%.
（2）The synthesis of compound 1
To addition compound III in 50 milliliters of reaction bulbs（Upper step product, 0.33 gram, 1 mM）, potassium carbonate (0.14
Gram, 1 mM, content>99%) and 5 milliliters of DMF solutions in, start stirring, temperature control at 80 DEG C, reaction 30 minutes, then
Temperature is reduced to 70 DEG C, allyl bromide, bromoallylene is added（0.12 gram, 1 mM, content>99%）, reacted at 70 DEG C 8 hours, reaction
After finishing, 100 milliliters of water and 250 milliliters of ethyl acetate are added, be extracted with ethyl acetate, be washed with water and wash, anhydrous sodium sulfate is done
Dry, after being concentrated under reduced pressure, residue passes through pillar layer separation（Petroleum ether:Ethyl acetate:Dichloromethane=10:1:1）, obtain 0.16 gram
Compound 1, white solid, m.p.74-76 DEG C, yield 43%.[α]D 25=+39（C=0.01, dichloromethane）.Chiral HPLC
Measure R:S=96:4, analysis condition is：DAICEL Chemical Industries.LTDAD-H type chiral columns,
Isopropanol：N-hexane=10：90, flow velocity 1.2mL/s, 254nm detection（Analysis method is similarly hereinafter）.
The synthesis of example 2, compound 2：
（1）(RS) synthesis of -2- (4- (hydroxyphenoxy)) methyl propionate
Will be to biphenol（11 grams, 100 mMs）It is added in DMSO, is subsequently adding potassium hydroxide（5.83 grams, 100 millis
Mole, content>96%）, 90 DEG C are heated to, react 1 hour, 10 DEG C are cooled to, it is slowly added dropwise compound 2 bromopropionic acid methyl esters
（4.17 grams, 25 mMs, content>99%, raceme), be poured into water for reaction solution by stirred overnight at room temperature, adds 50 milliliter two
Chloromethanes is extracted, and separates organic phase, and regulation water layer pH is 4, is then extracted with dichloromethane, merges organic phase, and precipitation depressurizes dense
After contracting, residue passes through pillar layer separation（Leacheate：Petroleum ether:Ethyl acetate=3:1）, obtain 4.30 grams of (RS) -2- (4- (hydroxyls
Phenoxyl)) methyl propionate, yellow oily liquid, yield 88%（In terms of 2 bromopropionic acid methyl esters）.
（2）(RS) synthesis of -4- (6- chloro benzo oxazoles epoxide)-phenoxy propionic acid methyl esters
By compound 2- (4- (hydroxyphenoxy)) methyl propionate（Upper step product, 2.52 grams, 12.8 mMs）, potassium carbonate
（2.13 grams, 15.4 mMs, content>99%）, in 30 milliliters of addition single port bottles of toluene, 70 DEG C of reaction half an hours, it is subsequently adding
Compound 2,6- dichloro benzoxazoles（2.90 grams, 15.4 mMs, content>99%）, heating reflux reaction 3 hours, after cooling,
100 milliliters of water and 100 milliliters of ethyl acetate are added, is extracted, after being concentrated under reduced pressure, residue passes through pillar layer separation（Leacheate：Stone
Oily ether:Ethyl acetate=4:1）, obtain 3.78 grams of (RS) -4- (6- chloro benzo oxazoles epoxide)-phenoxy propionic acid methyl esters, yellow oil
Shape liquid, yield 85%.
（3）The synthesis of intermediate (RS)-III
To addition (RS) -4- (6- chloro benzo oxazoles epoxide)-phenoxy propionic acid methyl esters in 500 milliliters of reaction bulbs（Upper step
Product, 34.78 grams, 100 mMs）And tetrahydrofuran（80 milliliters）, stirring to complete molten, the lower addition NaOH of cooling（4.13
Gram, 100 mMs, content>99%）And water（100 milliliters）The solution of formation, is warmed to room temperature stirring reaction 5 hours naturally, stops
Reaction, adds 100 milliliters of ethyl acetate extractions, and water is acidified with concentrated hydrochloric acid, and filtering, filtration cakes torrefaction obtains 26.80 grams of intermediates
(RS)-III, white solid, m.p.157-158 DEG C, yield 80%.
（4）The synthesis of compound 2
To addition intermediate (RS)-III in 50 milliliters of reaction bulbs（Upper step product, 0.33 gram, 1 mM）, potassium carbonate
(0.14 gram, 1 mM, content>99%) and in 5 milliliters of DMF solutions, stirring is started, temperature control is reacted 30 minutes at 80 DEG C,
Then temperature is reduced to 70 DEG C, adds allyl bromide, bromoallylene（0.12 gram, 1 mM, content>99%）, 8 hours are reacted at 70 DEG C,
After completion of the reaction, 100 milliliters of water and 250 milliliters of ethyl acetate are added, is extracted with ethyl acetate, be washed with water and wash, anhydrous slufuric acid
Sodium is dried, and after being concentrated under reduced pressure, residue passes through pillar layer separation（Leacheate：Petroleum ether:Ethyl acetate:Dichloromethane=10:1:
1）, obtain 0.26 g of compound 2, white solid, m.p.74-76 DEG C, R:S=50:50, yield 70%.
Other compounds in table 1 can be obtained by the method similar with above example.
It is raw to survey example
After active compound acetone solution, the to be measured of concentration needed for running water is prepared is stood with 1 ‰ Tween 80 by test requirements document
Liquid.Spraying treatment is carried out with crawler type crops sprayer (Britain Engineer Research Ltd. design production)（Spraying pressure
Power 1.95kg/cm2, spouting liquid 50mL/m2, crawler track speeds 30cm/s, nozzle is fan nozzle）.
Prevent and kill off barnyard grass activity test：Quantitative barnyard grass seed is sowed at sectional area for 100cm2Culturing pot in, covered after broadcasting
Native 1cm, cultivates according to a conventional method after suppression, water drenching in greenhouse.Treat that weeds are long to 1.5 leaf phases, choose the examination of growth uniformity
Material carries out after seedling cauline leaf spraying treatment, and water treatment as control is stood using 1 ‰ Tween 80.Drying is placed on after examination material treatment
Ventilation, after after liquid natural air drying, is placed in greenhouse and manages according to a conventional method, is used in 48 hours after treatment and is poured water from bottom
Method, it is to avoid liquid is washed.Range estimation investigation is carried out within 4 weeks after treatment, inhibiting rate is various degree of injury compared with the control,
Including kill, chlorosis, withered spot, distortion, deformity, growth inhibition or blade calcination etc..
Compound of Formula I has preventive effect high to barnyard grass, and wherein compound 1,2,3,5 is in 45g a.i./hm2Under to barnyard grass
Inhibiting rate more than 90%.
Compound 1 and its raceme compound 2 are chosen, has been carried out except barnyard grass with the R bodies and its raceme of known compound KC
The active parallel contrast test of grass, the results are shown in Table 2.
Table 2：Compound 1,2, expression activitiy is prevented and kill off with the R bodies of compound KC and its barnyard grass of raceme（After seedling, g
a.i./hm2, inhibiting rate %）
Note：KC（R bodies）And KC（Raceme）It is No. 131 compounds in US4130413A patents, does not refer to that its chiral carbon is former
Sub- configuration.The application carries out sample preparation with reference to method in US4130413A patents.KC（R bodies）And KC（Raceme）It is physical
Matter is shown in Table 3.
Table 3：KC（R bodies）And KC（Raceme）Physical property：
Security of rice is tested：Quantitative rice paddy seed is sowed at sectional area for 100cm2Culturing pot in, broadcast rear earthing
1cm, cultivates according to a conventional method after suppression, water drenching in greenhouse.Treat that paddy rice is long to 3 leaf phases, the examination material for choosing growth uniformity enters
Row after seedling cauline leaf spraying treatment, water treatment as control is stood using 1 ‰ Tween 80.Dry ventilation is placed on after examination material treatment
Place, after after liquid natural air drying, is placed in greenhouse and manages according to a conventional method, using the side poured water from bottom in 48 hours after treatment
Method, it is to avoid liquid is washed.Range estimation investigation is carried out within 4 weeks after treatment, inhibiting rate is various degree of injury compared with the control, including
Kill, chlorosis, withered spot, distortion, deformity, growth inhibition or blade calcination etc..
Compound of Formula I has security high to paddy rice, and wherein compound 1 is in 30g a.i./hm2Under dosage, to water
Rice inhibiting rate is only 10%.
Claims (4)
1. a kind of 6- chloros benzoxazole epoxide phenoxy propionic acid allyl ester type compound, as shown in formula I：
In formula：
R1、R2、R3And R4It is respectively selected from hydrogen；
The asymmetric carbon atom for marking * is R configurations.
2. the compound described in claim 1 is used to control the purposes of monocotyledon weed.
3. a kind of Herbicidal combinations, it is characterised in that containing compound as claimed in claim 1 and agriculturally acceptable load
Body, the weight percentage of active component is 1-99% in composition.
4. a kind of Herbicidal combinations as claimed in claim 3 control weeds method, it is characterised in that：To weeds or weeds
Somatomedin or place on apply weeding effective dose Herbicidal combinations as claimed in claim 3.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130413A (en) * | 1976-09-10 | 1978-12-19 | Hoechst Aktiengesellschaft | Heterocyclic phenyl ethers and herbicides containing same |
| WO1991004969A1 (en) * | 1989-10-05 | 1991-04-18 | Hoechst Aktiengesellschaft | Herbicidal, heterocyclically substituted phenoxyalkane carboxylic acid derivatives and process for preparing them |
| CN1662484A (en) * | 2002-06-26 | 2005-08-31 | 韩国化学研究院 | Process for preparing (r)-aryloxypropionic acid ester derivatives |
| CN1927843A (en) * | 2005-09-08 | 2007-03-14 | 沈阳化工研究院 | Compound of 2-substituted alkylacrylate and application thereof |
| CN103275029A (en) * | 2013-06-14 | 2013-09-04 | 南开大学 | Preparation and application research of novel water and oil soluble aryloxy-phenoxy propionate derivative |
-
2013
- 2013-11-25 CN CN201310606528.9A patent/CN104649995B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130413A (en) * | 1976-09-10 | 1978-12-19 | Hoechst Aktiengesellschaft | Heterocyclic phenyl ethers and herbicides containing same |
| WO1991004969A1 (en) * | 1989-10-05 | 1991-04-18 | Hoechst Aktiengesellschaft | Herbicidal, heterocyclically substituted phenoxyalkane carboxylic acid derivatives and process for preparing them |
| CN1662484A (en) * | 2002-06-26 | 2005-08-31 | 韩国化学研究院 | Process for preparing (r)-aryloxypropionic acid ester derivatives |
| CN1927843A (en) * | 2005-09-08 | 2007-03-14 | 沈阳化工研究院 | Compound of 2-substituted alkylacrylate and application thereof |
| CN103275029A (en) * | 2013-06-14 | 2013-09-04 | 南开大学 | Preparation and application research of novel water and oil soluble aryloxy-phenoxy propionate derivative |
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