CN106417298A - Application of (R)-2-[4-(4-cyano-2-fluorophenoxy) phenoxy] ethyl propionate as herbicide - Google Patents
Application of (R)-2-[4-(4-cyano-2-fluorophenoxy) phenoxy] ethyl propionate as herbicide Download PDFInfo
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- CN106417298A CN106417298A CN201610603236.3A CN201610603236A CN106417298A CN 106417298 A CN106417298 A CN 106417298A CN 201610603236 A CN201610603236 A CN 201610603236A CN 106417298 A CN106417298 A CN 106417298A
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- agricultural chemicals
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- herbicidal combinations
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- RAVFKDLABNXJFN-GFCCVEGCSA-N CCOC([C@@H](C)Oc(cc1)ccc1Oc(c(F)c1)ccc1C#N)=O Chemical compound CCOC([C@@H](C)Oc(cc1)ccc1Oc(c(F)c1)ccc1C#N)=O RAVFKDLABNXJFN-GFCCVEGCSA-N 0.000 description 1
Classifications
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- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
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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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses an application of (R)-2-[4-(4-cyano-2-fluorophenoxy) phenoxy] ethyl propionate as herbicide and particularly provides an application of a compound represented as a formula (I) or pharmaceutically acceptable salt of the compound in the aspect of crop weeding. The compound can be applied to the crop weeding, and experiments show that the compound has the advantages that the application amount is reduced, a broader weeding spectrum is obtained, and the compound takes effect quickly and has a more durable control effect and the like.
Description
Technical field
The invention belongs to pesticide field, be specifically related to a kind of compound (R)-2-[4-(4-cyano group-2-fluorophenoxy) benzene oxygen
Base] ethyl propionate is as the new application of herbicide.
Background technology
Administration chemical herbicide is means maximally efficient during farmland weed is prevented and kill off.But make articles for use long-term continuous high dose
Kind or the single chemical herbicide of the mode of action, easily cause residual, environmental pollution and weeds resistance and the resistance of herbicide
The problems such as development.Reasonably chemical herbicide is compounding or mixture has expansion weeds spectrum, and raising preventive effect, prolongation dispenser are fitted
Phase, minimizing dosage, reduction poisoning, minimizing remain, delay the features such as weeds drug resistance and drug-fast generation and development, are solutions
Certainly one of maximally efficient method of the problems referred to above, but these compounding bases being all built upon existing chemical herbicide
On.Therefore the herbicide of developing new product variety is only the basis in chemical weed control field.
Content of the invention
It is an object of the invention to provide compound (R)-2-[4-(4-cyano group-2-fluorophenoxy) phenoxy group] ethyl propionate
New application in terms of weeding for the compound.
It is a further object of the present invention to provide a kind of Herbicidal combinations containing above-claimed cpd.
The purpose of the present invention can be reached by following measures：
Compound shown in formula (I) or purposes in terms of crops weeding for its pharmaceutically acceptable salt,
One or more in cereal crops, industrial crops or vegetable crop of the crops of indication of the present invention.
In a kind of preferred version, one or more in paddy rice, wheat, beans, potato class, corn of crops.
The compound of the present invention or its pharmaceutically acceptable salt can be applicable to prevent and kill off broad leaved weed, sedge weed or standing grain
Undergraduate course weeds aspect.
In a kind of preferred version, one or more in barnyard grass, lady's-grass, rice Leersia Sw, moleplant seed of described weeds.
The present invention includes a kind of agricultural chemicals Herbicidal combinations, and it is with the compound shown in formula (I) or it is pharmaceutically acceptable
Salt is active component or main active.
In a kind of preferred version, said composition is made, by active component and auxiliary agent, the formulation allowing on agricultural chemicals.Particularly,
Said composition can be aided with, with active component, any one formulation that applicable agricultural use made by acceptable auxiliary material on agricultural chemicals, tool
Body, it can be with active component and to be aided with in pesticidal preparations the auxiliary agent of generally use, solvent, carrier auxiliary element each to make
Plant the formulation being suitable in agricultural using.
When this composition makes a certain concrete formulation, wherein active component mass content be 1.0001～
85.0001% or 3-90%, preferably 5～80%.Its formulation can be wettable powder, water dispersible granules, aqueous emulsion, dispersible
Oil-suspending agent, missible oil or suspending agent.
This Herbicidal combinations can be applicable to agriculture field and prevents and kill off crop weeds aspect, particularly agriculture field such as paddy rice
The aspects such as the barnyard grass in crops, lady's-grass, rice Leersia Sw, moleplant seed are prevented and kill off in field.
The composition of the present invention can be prepared as various formulation by available known method, can by active ingredient with help
Agent, such as solvent, solid carrier, uniformly can mix when needing together with surfactant or other components (such as solvent, carrier etc.)
Close, grind, the formulation required for being prepared as.
Suitable auxiliary agent can be solid or liquid, their materials conventional during being typically formulation, such as sky
Right or regeneration mineral matter, solvent, dispersant, wetting agent, adhesive, surfactant or fertilizer, a kind of selection can be selected, also
Multiple selection can be selected.
Above-mentioned solvent is selected from aromatic hydrocarbon, preferably contains 8-12 carbon atom, such as xylene mixture or substituted benzene, phthalein
Esters of gallic acid, such as Dibutyl phthalate or phthalandione two octanoic acid, fat hydrocarbon, such as thiacyclohexane or paraffin, alcohol and ethylene glycol and their ether
And ester, such as ethanol, ethylene glycol, ethylene glycol monomethyl；Ketone, such as cyclohexanone, highly polar solvent, such as N-methyl-2-pyrrolidines
Ketone, dimethyl sulfoxide (DMSO) or dimethylformamide, and vegetable oil or vegetable oil, such as soybean oil.
Above-mentioned carrier (particularly solid carrier), as pulvis and dispersible agent be typically natural mineral fillers,
Such as talcum, kaolin, montmorillonite or atlapulgite.In order to manage the physical property of composition, it is also possible to add polymolecularity
Silicic acid or polymolecularity adsorpting polymerization thing carrier, such as granulated adsorptive carriers or non-adsorbed carrier, suitable granulated adsorptive carriers
It is porous type, such as float stone, bentonite or bentonite；Suitable non-adsorbed carrier such as calcite or sand.Further, it is possible to use it is a large amount of
Inorganic in nature or organic nature be prefabricated into granular material as carrier, particularly dolomite.
According to the chemical property of the active ingredient in the composition of the present invention, suitable surfactant is sulfomethylated lignin
Acid, naphthalene sulfonic acids, phenolsulfonic acid, alkali salt or amine salt, alkylaryl sulfonates, alkyl sulfate, alkylsulfonate, fat
Alcohol sulfate, aliphatic acid and sulphated fatty alcohol glycol ether, the also condensation product of sulfonated naphthalene and naphthalene derivatives and formaldehyde, naphthalene or
Naphthalene sulfonic acids and the condensation product of phenol and formaldehyde, NONIN HS 240, ethoxylated isooctyl-phenol, octyl phenol, nonyl phenol,
Alkylaryl polyglycol ether, tributyl benzene polyglycol ether, three stearyl phenyl polyglycol ethers, alkyl aryl polyether alcohol,
Ethoxylated castor oil, polyoxyethylene alkyl ether, ethylene oxide condensation product, ethoxylation polyoxypropylene, laurate polyethylene glycol
Ether acetal, sorbitol ester, lignin sulfite waste liquor and methylcellulose.
The application process of the present composition includes the aerial part that the composition of the present invention is used for plant growth, including
Leaf portion or blade face.The growth place of plant, such as rice field can be soaked by the liquid preparation of composition, or by composition with
Solid form is applied in soil, and as in granular form (soil application), composition can be planted through plant root entrance by soil
In object (systemic action).
These compositions can only comprise active component and be administered, it is also possible to mix together with additive, because of
The composition of this present invention can be prepared as the current published various formulations of pesticide, for example wettable powder, water dispersible granules,
Aqueous emulsion, microemulsion, missible oil, suspending agent, microcapsule formulations, dispersible oil-suspending agent etc..Character according to these compositions
And administration composition purpose to be reached and ambient conditions, can select composition to spray, atomizing, dust, broadcast sowing
Or sprinkle the method administration watered or the like.
The compound of the present invention can be applicable to crops weeding aspect, experiment discovery it have amount of application reduce, broader
The advantages such as weed control spectrum, instant effect, more longlasting prevention effect.
Brief description
Fig. 1 is the nucleus magnetic hydrogen spectrum of compound shown in formula (I) of the present invention；
Fig. 2 is the nuclear-magnetism carbon spectrum of compound shown in formula (I) of the present invention；
Fig. 3 is the GC-MS hydrogen spectrum of compound shown in formula (I) of the present invention.
Detailed description of the invention
Some aspects of the present invention and embodiment can be further illustrated with by following specific embodiment.This
The compound covered in bright can be synthesized by known conventional art.These compounds can be from readily available initiation material
Advantageously synthesize.The following is the general synthetic schemes of compound of present invention synthesis.These schemes disclosed herein are illustrative,
It is not offered as limiting those skilled in the art and use other possible method synthesis compounds.Various methods are all in this area
Routine techniques.
Representational example is intended to help to illustrate the present invention below, rather than has a mind to also should not be construed as limited to this
The scope of invention.It is true that in addition to those occur and be described herein, the full content of file in the present invention, including depend on
According to the example of scientific and technical literature cited herein and patent, and consequent various modification is further change in this special with many
Those skilled in the art are clear clear in the industry.It should also be appreciated that quoting of these bibliography contributes in statement herein
Hold.The examples below contains important side information, example and guidance, is adaptable to various changes and similar feelings in the present invention
Condition.
Synthetic example
Embodiment 1：The synthesis of formula (I) compound (R) 2 [4 (4 cyano group 2 fluorophenoxy) phenoxy group] ethyl propionate
Method
The synthesis of 1.1 etherates
1.1.1 synthetic route：
1.1.2 operation：
1.1.2.1 HPPA is put into：85g, DMF：150g, oil bath now begins to warm up,
1.1.2.2 throwing and finishing, stirring is lower puts into 187g powdered potassium carbonate, is first slowly added to, has a large amount of bubble to produce, treats gas
Bubble amount reduces, and accelerates rate of feeding,
1.1.2.3 finish, be gradually heating to 80 DEG C,
1.1.2.4 about 67 DEG C when start to drip the mixed solution of cyanophenyl 50g and DMF50g, time for adding is 1 little
When, control temperature between 67～71,
1.1.2.5 drip complete, stir 15 minutes, detection, cyanophenyl content is less than 1%,
1.1.2.6 add in 1000g water,
1.1.2.7 finishing, with 16% salt acid for adjusting pH to 7, system is clarified, then continue acid adjustment, if muddy, then first filter,
1.1.2.8 regulation terminates, and stirs 15 minutes, and repetition measurement ph is 3～4, suction filtration,
1.1.2.9 solids washed with water, 50 degree of vacuum dryings, obtain dry product 134g, yield：95.7%, content：
97.5%.
The synthesis of 1.2 acyl chlorides
1.2.1 synthetic route
1.2.2 operation：
1.2.2.1 put into 200g 227 etherate, add 700g dichloroethanes, under stirring, be warming up to 45～50 DEG C,
1.2.2.2 drip 84g oxalyl chloride, about 1 hour drip finish, be incubated 0.5 hour, sampling detect, qualified after be directly entered
Next step.
The synthesis of 1.3 esters
1.3.1 synthetic route
1.3.2 operation
1.3.2.1 put into 300g ethanol in four-hole bottle, be cooled to 5 DEG C,
1.3.2.2 the lower dropping 227 acyl chlorides (being prepared by 200g 227 etherate) of stirring, controls temperature 5 DEG C,
1.3.2.3 dripping complete, reacting 0.5 hour, it is qualified to detect, and (is owing to color is redness before, adds 10g activated carbon
Decolour, then separate out crystal), can directly be cooled to 10 DEG C, separate out solid, use ice ethanol rinse.40 DEG C of drying, obtain
White solid 205g, yield：96.2%, content 98%.
Formula (I) compound molecule formula：C18H16FNO4, formula (I) fusing point：68.9‐70.5℃.Its chemical structure data is shown in Fig. 1
3.
Example of formulations
Embodiment 2：85% water dispersible granules
Active component 85%, Negel 3%, methyl naphthalene sulfonate formaldehyde condensate 4%, dodecyl sodium sulfate
2%, precipitated calcium carbonate complements to 100%.Active component formula (I) compound is mixed all in the ratio of formula with auxiliary agent and filler
Even, become wettable powder through air-flow crushing, add a certain amount of water mixing extruder grain, prepare water-dispersible after drying screening
Granula product.
Embodiment 3:65% wettable powder
Active component 65%, pulls open powder 3%, neopelex 2%, and bentonite 3%, attapulgite complements to
100%.Active component formula (I) compound is sufficiently mixed in proportion with various auxiliary agents and filler etc., through ultra-fine pulverizer disintegrating
Rear prepared wettable powder.
Embodiment 4：12% microemulsion
Active component 12%, acetone 10%, urea 4%, propane diols 3%, compound sodium nitrophenolate 0.5%, alkyl polyoxyethylene ether
With NPE 2%, water complements to 100%.After active component formula (I) compound is completely dissolved in a solvent,
It is stirred, is simultaneously introduced emulsifying agent, builder and antifreeze, after above-mentioned system mixes, then water is slowly added into above-mentioned
In mixed liquor, the microemulsion of different content after being sufficiently stirred for, can be made into.
Embodiment 5：10% emulsifiable concentrate
Active component 10%, emulsifying agent 25%, surfactant 35%, oils 30%.Each component is mixed,
Sand mill is ground to active ingredient particle diameter and is less than 3 μm.
Embodiment 6:10% oil-suspending agent
Active component 10%, xanthans 2%, calcium lignosulfonate 9%, mineral oil complements to 100%.By each component by than
Example is sufficiently mixed, and adds active component, grinds in sand mill, grind until a range of grain under high speed shear agitation
Footpath.
Drug effect verifies embodiment
Embodiment 7：
10% made missible oil of Example 5, sprayed in about the paddy rice 3 leaf phase.Water in field is drained, 1-2 after dispenser before dispenser
Its backwater, and water conservation 5-7 days, water layer 3-5 centimetre.Consumption 100 grams/acre, even spraying after being watered 15-20 kilogram.Shake before medication
Even, double dilution method.Note：High temperature not medication at noon.
Dispenser in the rice terrace containing barnyard grass 1.5-2 leaf, lady's-grass 1.5 leaf, rice Leersia Sw 1.5-2 leaf respectively, its result
It is shown in Table 1-3.
Table 1
Table 2
Table 3
Embodiment 8：
10% made oil-suspending agent of Example 6, sprayed in about the paddy rice 4.5 leaf phase.Water in field, dispenser is drained before dispenser
Latter 1-2 days backwater, and water conservation 5-7 days, water layer 3-5 centimetre.Medicament be watered 15-20 kilogram after even spraying.Shake up before medication, two
Secondary dilution method.Note：High temperature not medication at noon.
Dispenser in the rice terrace containing barnyard grass 4 leaf, lady's-grass 3-4 leaf, rice Leersia Sw respectively, it the results are shown in Table 4-7.
Table 4
Table 5
Table 6
Table 7
Claims (10)
1. the compound shown in formula (I) or purposes in terms of crops weeding for its pharmaceutically acceptable salt,
2. purposes according to claim 1, it is characterised in that described crops are selected from cereal crops, industrial crops or vegetables
One or more in crop.
3. purposes according to claim 2, it is characterised in that described crops are selected from paddy rice, wheat, beans, potato class, jade
One or more in meter.
4. purposes according to claim 1, it is characterised in that the compound shown in described formula (I) or it is pharmaceutically acceptable
Purposes in terms of preventing and kill off broad leaved weed, sedge weed or grassy weed for the salt.
5. purposes according to claim 4, it is characterised in that described weeds are selected from barnyard grass, lady's-grass, rice Leersia Sw, moleplant seed
In one or more.
6. an agricultural chemicals Herbicidal combinations, it is characterised in that it is with the compound described in claim 1 or it is pharmaceutically acceptable
Salt be active component or main active.
7. agricultural chemicals Herbicidal combinations according to claim 6, it is characterised in that said composition is by active component and auxiliary agent system
Become the formulation allowing on agricultural chemicals.
8. agricultural chemicals Herbicidal combinations according to claim 7, it is characterised in that in said composition, the quality of active component contains
Amount is 1.0001～85.0001%.
9. agricultural chemicals Herbicidal combinations according to claim 8, it is characterised in that in said composition, the quality of active component contains
Amount is 5～80%.
10. agricultural chemicals Herbicidal combinations according to claim 7, it is characterised in that described formulation is selected from wettable powder, water
Dispersible granule, aqueous emulsion, dispersible oil-suspending agent, missible oil or suspending agent.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610249149 | 2016-04-20 | ||
| CN2016102491492 | 2016-04-20 |
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| CN201610603236.3A Pending CN106417298A (en) | 2016-04-20 | 2016-07-27 | Application of (R)-2-[4-(4-cyano-2-fluorophenoxy) phenoxy] ethyl propionate as herbicide |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115490617A (en) * | 2022-10-14 | 2022-12-20 | 江苏丰山集团股份有限公司 | Preparation process of low-cost high-light pure content cyhalofop-butyl |
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| EP0138359A2 (en) * | 1983-09-01 | 1985-04-24 | The Dow Chemical Company | Herbicidal Fluorophenoxyphenoxypropionates, derivatives thereof and related compounds |
| EP0302203A1 (en) * | 1987-08-05 | 1989-02-08 | Dowelanco | Herbicidal fluorophenoxyphenoxyalkanoic acids and derivatives thereof |
| CN1105172A (en) * | 1993-04-16 | 1995-07-12 | 唐艾兰科公司 | Herbicidal composition |
| CN102181496A (en) * | 2011-03-01 | 2011-09-14 | 安徽安生生物化工科技有限责任公司 | Enzymatic synthesis method for fenpyroxim |
-
2016
- 2016-07-27 CN CN201610603236.3A patent/CN106417298A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0138359A2 (en) * | 1983-09-01 | 1985-04-24 | The Dow Chemical Company | Herbicidal Fluorophenoxyphenoxypropionates, derivatives thereof and related compounds |
| EP0302203A1 (en) * | 1987-08-05 | 1989-02-08 | Dowelanco | Herbicidal fluorophenoxyphenoxyalkanoic acids and derivatives thereof |
| US4894085A (en) * | 1987-08-05 | 1990-01-16 | The Dow Chemical Company | Herbicidal cyanofluorophenoxyphenoxyalkanoic acids and derivatives thereof |
| CN1105172A (en) * | 1993-04-16 | 1995-07-12 | 唐艾兰科公司 | Herbicidal composition |
| CN102181496A (en) * | 2011-03-01 | 2011-09-14 | 安徽安生生物化工科技有限责任公司 | Enzymatic synthesis method for fenpyroxim |
Non-Patent Citations (2)
| Title |
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| 张涛等: ""氰氟草酯手性合成催化剂的筛选"", 《安徽化工》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115490617A (en) * | 2022-10-14 | 2022-12-20 | 江苏丰山集团股份有限公司 | Preparation process of low-cost high-light pure content cyhalofop-butyl |
| CN115490617B (en) * | 2022-10-14 | 2024-03-26 | 江苏丰山生化科技有限公司 | Preparation process of cyhalofop-butyl with low cost and high optical purity content |
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Application publication date: 20170222 |