CN108059630A - A kind of 6- chloros benzoxazole oxygroup benzene oxygen Propionamides compound and its application - Google Patents
A kind of 6- chloros benzoxazole oxygroup benzene oxygen Propionamides compound and its application Download PDFInfo
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- CN108059630A CN108059630A CN201610978684.1A CN201610978684A CN108059630A CN 108059630 A CN108059630 A CN 108059630A CN 201610978684 A CN201610978684 A CN 201610978684A CN 108059630 A CN108059630 A CN 108059630A
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- general formula
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- benzoxazole
- weeds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- A01N43/80—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 1,2
Abstract
The present invention discloses a kind of 6 chloro benzoxazole oxygroup benzene oxygen Propionamides compound and its application as herbicide, and the compound is as shown in logical formula (I)：Wherein：W is selected from C1‑4Alkylidene.The compound of the present invention not only has excellent activity of weeding, and to crop safety.
Description
Technical field
The invention belongs to chemical fields.Specifically a kind of 6- chloros benzoxazole oxygroup benzene oxygen Propionamides compound
And its application.
Background technology
Due to the succession of weed population, transition and to the drug-fast generation of chemical pesticide and rapid development, people are to life
The continuous reinforcement of state environmental protection consciousness, the understanding influenced on chemical pesticide pollution, pesticide on non-target organism and in pesticide
The attention of home to return to problem is continuously improved in ecological environment.With the gradually decreasing of world's cultivated area, population it is continuous increase and
Increase to grain demand amount forces people to rapidly develop agriculture production technology, improves and improve cropping system, and needs constantly hair
Bright new and improved herbicides compounds and composition.
CN103965123A, which reports the thick miscellaneous phenoxy carboxylic acyloxy aminated compounds of some N- oxygroups, can be used as herbicide, example
Such as No. 12 compound K C therein (asymmetric carbon atom that * is represented is R configurations)：
6- chloro benzoxazole oxygroup benzene oxygen Propionamides compounds as representative of the present invention are not disclosed.
The content of the invention
The object of the present invention is to provide a kind of 6- chloros benzoxazole oxygroup benzene oxygen Propionamides compounds and its conduct to remove
The application of careless agent.
To achieve the above object, the technical scheme is that：
A kind of 6- chloros benzoxazole oxygroup benzene oxygen Propionamides compound, compound is as shown in general formula I：
In formula：
W is selected from C1-4Alkylidene；
Optionally, in the general formula I：
W is selected from CH2, CH2CH2, CH2CH2CH2Or CH2CH2CH2CH2。
Optionally, in the general formula I：
W is selected from CH2Or CH2CH2。
Optionally, in general formula I：
W is selected from CH2。
Optionally, compound shown in the general formula I is R types or S type structures；Specifically, compound shown in above-mentioned general formula I with
The carbon atom of * is marked as asymmetric carbon atom, S-type or R type structures.
Still optionally further, compound shown in the general formula I is R configurations.
The present invention also provides compound shown in a kind of general formula I for controlling the purposes in weeds.
The present invention provides a kind of Herbicidal combinations again, Herbicidal combinations using as shown in general formula I compound as activity
Ingredient and agriculturally acceptable carrier, the weight percentage of active component is 1-99% in composition.
Invention further provides a kind of method of the control weeds of Herbicidal combinations, somatomedin to weeds or weeds or
The Herbicidal combinations of weeding effective dose are applied on place.
The general formula compound I of the present invention can be prepared by the following method：
By raw material II, (R=Et can be bought by market；R=Me can refer to US4130413A and be made) it is dissolved in suitable solvent
In 1, and be added in alkaline aqueous solution, temperature for -10 DEG C to react between suitable 1 boiling point of solvent 0.5-48 it is small when, then pass through
Hydrochloric acid or sulfuric acid acidifying, it is compound III that intermediate acid, which is made,.Suitable solvent 1 be selected from chloroform, dichloromethane, carbon tetrachloride,
N-hexane, benzene, toluene, ethyl acetate, methanol, ethyl alcohol, tetrahydrofuran or dioxane etc.；Alkali is selected from hydrogen-oxygen in alkaline aqueous solution
Change sodium, potassium hydroxide, sodium carbonate, potassium carbonate or sodium acid carbonate etc..
Gained intermediate acid III is dissolved in suitable solvent 2, adds in the hydrochloride of corresponding amine, and adds in alkaloids, then
Condensing agent is added in, is eventually adding catalyst 4-dimethylaminopyridine, temperature is reacted for -10 DEG C between suitable 2 boiling point of solvent
When 0.5-48 is small, object I is made.
Suitable solvent 2 for chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran,
N,N-dimethylformamide or dioxane etc.；Alkaloids for triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate,
Potassium carbonate, sodium acid carbonate etc.；Condensing agent is 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate, dicyclohexyl
Carbodiimide, N, N- diisopropylcarbodiimide etc..
Or intermediate acid III is dissolved in suitable solvent 3, first and thionyl chloride, oxalyl chloride, phosphorus oxychloride, tribromo oxygen
The reagent reactings such as phosphorus, phosphorus trichloride, carbonyl dimidazoles, Cyanuric Chloride prepare acylating reagent, are then added to containing alkaloids
In the suitable solution of alcoxyl amine, temperature for -10 DEG C to react between suitable 3 boiling point of solvent 0.5-48 it is small when, object is made
I。
Suitable solvent 3 is selected from chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, tetrahydrochysene furan
It mutters or dioxane etc.；Contain alkaloids such as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, carbonic acid
Hydrogen sodium etc..
Table 1：The compounds of this invention of the part as shown in general formula I
The compound of Formula I of the present invention has activity of weeding, available for agriculturally preventing a variety of weeds.With prior art institute
Disclosed compound is compared, and 6- chloro benzoxazole oxygroup benzene oxygen propanamide compounds of the invention not only have excellent weeding
Activity, and to crop safety.
Present invention additionally comprises the Herbicidal combinations using compound of Formula I as active component.Activearm in the Herbicidal combinations
The weight percentage divided is 1-99%.Agriculturally acceptable carrier is further included in the Herbicidal combinations.
The Herbicidal combinations of the present invention can be applied in the form of several formulations.Usually the compound of the present invention is dissolved or divided
It dissipates more readily dispersible when being configured to preparation in carrier to be used as herbicide.Such as：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 in, and is usually needed
Add in appropriate surfactant.
The present invention also provides the implementation of controlling weeds, this method is included the weeding of the present invention of herbicidally effective amount
Composition is imposed on the place of the weeds or the weed growth or the surface of its growth medium.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.It, can removing in the present invention for some applications
One or more other herbicides are added in careless composition, thus can generate the advantages of additional and effect.
The compound of the present invention both can be used alone can also be with other known insecticide, fungicide, plant growth
Conditioning agent or fertilizer etc. mix 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.
Embodiment
The compounds of this invention shown in general formula I obtained according to above-mentioned record is as shown in the table,
Table 2
Compound in above-mentioned table 21H NMR(300MHz,CDCl3) data are as follows：
Compound 1：7.43–7.22(m,5H),6.99–6.96(d,2H),5.17–5.14(m,1H),4.08–4.03(t,
2H),3.83–3.73(m,2H),2.42–2.33(m,2H),1.61–1.59(d,3H)。
Compound 2：7.44–7.23(m,5H),6.99–6.96(m,2H),5.18–5.15(m,1H),4.08–4.04(t,
2H),3.83–3.77(m,2H),2.40–2.35(m,2H),1.61–1.59(d,3H)。
Compound 3：7.43–7.23(m,5H),6.98–6.95(d,2H),5.19–5.17(m,1H),4.04–4.02(m,
2H),3.86–3.76(m,2H),1.86–1.77(m,4H),1.60–1.58(d,3H)。
Compound 4：7.44–7.23(m,5H),6.99–6.95(d,2H),5.20–5.17(m,1H),4.04–4.03(m,
2H),3.88–3.75(m,2H),1.86–1.78(m,4H),1.60–1.58(d,3H)。
Compound 5：7.44–7.23(m,5H),6.99–6.96(d,2H),5.19–5.16(m,1H),4.09–4.07(m,
2H),3.90–3.66(m,2H),1.81(m,6H),1.62–1.60(d,3H)。
Synthesize example
The synthesis of 1 compound 1 of synthesis example：
(1) synthesis of intermediate (R)-III
Into 1000 milliliters of reaction bulb add in fenoxaprop (50.00 grams, 138 mMs, purchased from Jiangsu Feng Shanji
Co., Ltd of group, the asymmetric carbon atom for marking * are R configurations) and 200 milliliters of tetrahydrofurans, are stirred to complete molten, the lower addition hydrogen-oxygen of cooling
Change the solution that sodium (8.30 grams, 208 mMs) and 200 milliliters of water are formed, be warmed to room temperature naturally be stirred to react 5 it is small when, stop instead
Should, decompression steams tetrahydrofuran, adds in 200 milliliters of ethyl acetate extractions, and water is mutually acidified with concentrated hydrochloric acid, after solid fully is precipitated,
Filtering, filter cake washing solid twice, dry 38.50 grams of intermediate acid (R)-III, Light brown solid, m.p.157-158 DEG C,
Yield 83%.
(2) synthesis of compound 1
Compound (R)-III (above walk product, 10.00 grams, 30.0 mMs) is added in into 500 milliliters of reaction bulb, it is different
Oxazolidine hydrochloride (3.30 grams, 30.1 mMs) and 200 milliliters of dichloromethane, sequentially add triethylamine (3.10 grams, 30.6
MM) and 4-dimethylaminopyridine (0.5 gram), stirring is started, 1- ethyls-(3- dimethylaminos third are added portionwise at room temperature
Base) phosphinylidyne diimmonium salt hydrochlorate (8.60 grams, 44.9 mMs), then reacts 5 hours, after completion of the reaction, adds at room temperature
200 milliliters of water extractions, 200 milliliters of dilute hydrochloric acid of organic layer (1 mol/L) are washed, and 200 milliliters of dilute sodium hydroxides (1 mol/L) are washed,
200 milliliters of saturated common salts are washed 2 times, and anhydrous magnesium sulfate drying, after being concentrated under reduced pressure, residue passes through pillar layer separation (petroleum ether：
Ethyl acetate=30:70) 1 8.70 grams of compound, is obtained, white solid, m.p.114-115 DEG C, yield 75%.[α]D 25=+
68.4 ° (c=0.0086, dichloromethane).Chiral HPLC measures R:S=100:0, analysis condition is：DAICEL
Chemical Industries.LTDAD-H type chiral columns, isopropanol：N-hexane=10：90, flow velocity
1.2mL/s, 254nm detect (analysis method is similarly hereinafter).
The synthesis of 2 compound 2 of synthesis example：
(1) synthesis of (RS) -2- (4- (hydroxyphenoxy)) methyl propionate
Biphenol (11.00 grams, 100 mMs) will be added in 40 milliliters of dimethyl sulfoxide (DMSO)s, and then add in hydroxide
Potassium (2.81 grams, 50 mMs), starts stirring, be slowly added dropwise at room temperature compound 2 bromopropionic acid methyl esters (8.35 grams, 50 mmoles
You, content>99%, raceme), it is stirred overnight at room temperature, reaction solution is poured into 200 milliliters of water, adds in 50 milliliters of dichloromethane
Extraction separates organic phase, and it is 4 to adjust water layer pH, is then extracted with dichloromethane, merges organic phase, and anhydrous magnesium sulfate drying subtracts
After pressure concentration, residue passes through pillar layer separation (petroleum ether：Ethyl acetate=20:80) 6.32 grams of (RS) -2- (4- (hydroxyls, are obtained
Phenoxyl)) methyl propionate, colourless oil liquid, yield 64.4% (in terms of 2 bromopropionic acid methyl esters).
(2) synthesis of (RS) -4- (6- chloro benzoxazoles oxygroup)-phenoxy propionic acid methyl esters
By compound 2- (4- (hydroxyphenoxy)) methyl propionate (above walk product, 1.97 grams, 10 mMs), potassium carbonate
(1.38 grams, 10 mMs), 20 milliliters of DMF are added in single port bottle, 80 DEG C of reaction half an hours, then add in compound 2,6- bis-
Chlorine benzoxazole (1.88 grams, 10 mMs) when 80 DEG C of reactions 4 are small, after cooling, adds in 100 milliliters of water and 100 milliliters of acetic acid second
Ester, extraction, after being concentrated under reduced pressure, residue passes through pillar layer separation (petroleum ether：Ethyl acetate=80:20) 2.31 grams, are obtained
(RS) -4- (6- chloro benzoxazoles oxygroup)-phenoxy propionic acid methyl esters, yellow oily liquid, yield 66%.
(3) synthesis of intermediate (RS)-III
(RS) -4- (6- chloro benzoxazoles oxygroup)-phenoxy propionic acid methyl esters (upper step is added in into 100 milliliters of reaction bulb
Product, 2.31 grams, 6.64 mMs) and tetrahydrofuran (10 milliliters), it stirs to complete molten, addition sodium hydroxide (0.40 under cooling down
Gram, 10.00 mMs) and the formation of (10 milliliters) of water solution, be warmed to room temperature naturally be stirred to react 5 it is small when, stop reaction, decompression
Steam tetrahydrofuran, after adding 20 milliliters of water, reenter the extraction of 20 milliliters of ethyl acetate, liquid separation, water mutually with dense salt tune PH 4~5, with
50 milliliters of ethyl acetate extract 2 times, merge organic phase, and precipitation is depressurized in anhydrous magnesium sulfate drying, obtain 1.95 grams of intermediates (RS)-
III, brown fluid, yield 88%.
(4) synthesis of compound 2
Compound (RS)-III (above walk product, 0.36 gram, 1.08 mMs) is added in into 100 milliliters of reaction bulb, it is different
Oxazolidine hydrochloride (0.12 gram, 1.09 mMs) and 30 milliliters of dichloromethane, sequentially add triethylamine (0.12 gram, 1.19
MM) and 4-dimethylaminopyridine (0.05 gram), stirring is started, 1- ethyls-(3- dimethylaminos third are added portionwise at room temperature
Base) phosphinylidyne diimmonium salt hydrochlorate (0.40 gram, 2.09 mMs), then reacts 5 hours, after completion of the reaction, adds at room temperature
30 milliliters of water extractions, 30 milliliters of dilute hydrochloric acid of organic layer (1 mol/L) are washed, and 30 milliliters of dilute sodium hydroxides (1 mol/L) are washed, 30 millis
It rises saturated common salt to wash 2 times, anhydrous magnesium sulfate drying, after being concentrated under reduced pressure, residue passes through pillar layer separation (petroleum ether:Acetic acid
Ethyl ester=30:70) 2 0.20 grams of compound, is obtained, yellow solid, m.p.124-125 DEG C, yield 48%.Chiral HPLC is surveyed
Obtain R:S=49:51.
Other compounds shown in other compounds or general formula I in table 1 can pass through the method similar with above example
It is made, is the prior art, is not repeating.
It is raw to survey example
After active compound acetone solution, as test requirements document with 1 ‰ Tween 80 stand tap water prepare needed for concentration it is to be measured
Liquid.Spraying treatment (spraying pressure is carried out with crawler type crops sprayer (Britain Engineer Research Ltd. designs production)
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 in the culturing pot that sectional area is 100cm2, is covered after broadcasting
Native 1cm is cultivated according to a conventional method after suppression, water drenching in greenhouse.It treats that weeds were grown to 1.5 leaf phases, chooses and grow uniform examination
Material carries out cauline leaf spraying treatment after seedling, and water treatment is stood as control using 1 ‰ Tween 80.Examination material processing is placed on operation
Hall after liquid natural air drying, is placed in greenhouse and manages according to a conventional method, interior when 48 is small after processing to use what is poured water from bottom
Method avoids liquid from being washed.21 days range estimation investigation test compounds are to the preventive effect of barnyard grass after processing.
The multiple embodiments of compound of Formula I have carried out removing the parallel contrast test of barnyard grass activity with known compound KC, as a result
It is shown in Table 3.
Table 3：The compounds of this invention prevents and kill off barnyard grass activity with compound KC's (after seedling, preventive effect %)
Note：" " represent not test.KC is No. 12 compounds in CN10396123A patents, is recorded according to the document and carries out sample
It is prepared by product.The physical property of KC is shown in Table 4.
Table 4：The physical property of KC：
Security of rice is tested：Quantitative rice paddy seed is sowed at sectional area as 100cm2Culturing pot in, broadcast rear earthing
1cm is cultivated according to a conventional method after suppression, water drenching in greenhouse.Rice length is treated to 3 leaf phases, choose the uniform examination material of growth into
Cauline leaf spraying treatment after row seedling stands water treatment as control using 1 ‰ Tween 80.Dry and ventilated is placed on after examination material processing
Place, after liquid natural air drying, is placed in greenhouse and manages according to a conventional method, interior using the side poured water from bottom when 48 is small after processing
Method avoids liquid from being washed.Range estimation investigation is carried out within 4 weeks after processing, 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 high security to rice, such as compound 1 is in 30 or 90g a.i./hm2Dosage
Under, it is 0 to poisoning after rice seedlings.In 30g a.i./hm2Under dosage, prior art compound K C is to poisoning after rice seedlings
15%.
Meanwhile other compounds in table 1 or other compounds shown in general formula I are respectively provided with corresponding herbicide effect.
Claims (9)
1. a kind of 6- chloros benzoxazole oxygroup benzene oxygen Propionamides compound, it is characterised in that：Compound is as shown in general formula I：
In formula：
W is selected from C1-4Alkylidene.
2. compound as described in claim 1, which is characterized in that in general formula I：
W is selected from CH2, CH2CH2, CH2CH2CH2Or CH2CH2CH2CH2。
3. compound as claimed in claim 2, which is characterized in that in general formula I：
W is selected from CH2Or CH2CH2。
4. compound as claimed in claim 3, which is characterized in that in general formula I：
W is selected from CH2。
5. the compound as described in Claims 1 to 4 any claim, which is characterized in that in general formula I：
The compound is R types or S type structures.
6. compound as claimed in claim 5, which is characterized in that in general formula I：
The compound is R type structures.
7. a kind of compound described in claim 1 is for controlling the purposes in weeds.
8. a kind of Herbicidal combinations, it is characterised in that：Herbicidal combinations using compound as described in claim 1 as activity
Ingredient and agriculturally acceptable carrier, the weight percentage of active component is 1-99% in composition.
9. a kind of method of the control weeds of Herbicidal combinations as claimed in claim 8, it is characterised in that：To weeds or weeds
Somatomedin or place on apply weeding effective dose the Herbicidal combinations.
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Citations (3)
| 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 |
| CN103965123A (en) * | 2013-01-31 | 2014-08-06 | 湖南化工研究院 | N-oxyl fused heterocycle oxy phenoxy carboxylic acid amide compound having biological activity, and preparation method thereof |
| CN105820134A (en) * | 2016-03-24 | 2016-08-03 | 山东海诺格生物科技有限公司 | Compound with herbicidal activity and preparation method and application thereof |
-
2016
- 2016-11-08 CN CN201610978684.1A patent/CN108059630B/en active Active
Patent Citations (3)
| 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 |
| CN103965123A (en) * | 2013-01-31 | 2014-08-06 | 湖南化工研究院 | N-oxyl fused heterocycle oxy phenoxy carboxylic acid amide compound having biological activity, and preparation method thereof |
| CN105820134A (en) * | 2016-03-24 | 2016-08-03 | 山东海诺格生物科技有限公司 | Compound with herbicidal activity and preparation method and application thereof |
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| CN108059630B (en) | 2020-04-14 |
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