CN105669584A - High-selectivity herbicide N-substitutive alkyl aryloxy phenoxyl propanamide compound and preparation and application thereof - Google Patents

High-selectivity herbicide N-substitutive alkyl aryloxy phenoxyl propanamide compound and preparation and application thereof Download PDF

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CN105669584A
CN105669584A CN201610137493.2A CN201610137493A CN105669584A CN 105669584 A CN105669584 A CN 105669584A CN 201610137493 A CN201610137493 A CN 201610137493A CN 105669584 A CN105669584 A CN 105669584A
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李为忠
赵静
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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
    • 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
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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 novel N-substitutive alkyl aryloxy phenoxyl propanamide with herbicidal activity represented by the formula (I) and a preparation method thereof, a purpose of controlling vacious grassy weeds in a rice field and a proper weeding composition.The formula (I) is shown in the description.In the formula, R1 is selected from hydrogen or C1-C6 alkane, R3 is selected from hydrogen or C1-C6 alkyl groups or C1-C6 halogenated alkyl groups or C2-C6 alkenyl or C2-C6 alkine groups or C5-C12 aryl groups or heterocyclic aryl, Ar is selected from C6-C12 aryl and C5-C12 heterocyclic aryl, part or all of hydrogen atoms in aryl and heterocyclic aryl are replaced with identical or different substituent groups selected from halogen, cyanogroups, nitryl, C1-C6 alkyl groups, C1-C6 alkoxy, C1-C6 alkylthiol, C1-C6 alkyl amidogen, C1-C6 halogen alkyl and C1-C6 halogen alkoxy, x is selected from N and O, and chiral carbon atoms marked with * are of R or S configuration or are a mixture with R and S with different proportions.

Description

High selective herbicide N-replaces alkyl virtue phenoxy base Propionamides compound and preparation and application thereof
Technical field
The invention belongs to pesticide field, for controlling compound and the preparation and application thereof of the weeds such as rice terrace barnyard grass.
Background technology
Oryza sativa L. is the topmost cereal crops of China, one of Ye Shi world staple food crop. Whole world Monitoring of Paddy Rice Plant Area about 1.45 hundred million hectares. China's rice growing area accounts for the 1/4 of whole nation cereal crops. Oryza sativa L. occupy the first in China cereal crops. Oryza sativa L. crop smothering area accounts for more than the 46% of the total cultivated area of Oryza sativa L., and Oryza sativa L. crop smothering major part is planted weeds by barnyard grass, Semen Euphorbiae, Herba Eleusines Indicae, Herba Cyperi Difformis etc. more than 10 and caused, wherein especially with barnyard grass, Semen Euphorbiae and Herba Eleusines Indicae, rice hazard is maximum. Virtue phenoxy compounds has the significantly high activity preventing and kill off grassy weed. The aryloxyphenoxypropanoates compounds being presently used for rice terrace postemergence weed control has two kinds:
Cyhalofop-butyl is in the aryloxyphenoxypropanoates class herbicide for agent for removing grass in paddy field of Development and Production in 1987 by Tao Shi benefit agriculture, and rice terrace Semen Euphorbiae is had good preventive effect. Unfortunately that the pernicious grassy weed preventive effects such as rice terrace Herba Digitariae, variation barnyard grass is very poor, almost without drug effect;
Azoles acyl grass amine be by Korea S Chemical Engineering Technology academy exploitation another kind can be used for the aryloxyphenoxypropanoates class herbicide of agent for removing grass in paddy field. Advantage is that many grassy weeds are had good preventive effect, unfortunately that a lot of biggrassweeds and the malignant weed preventive effect such as Paspalum distichum, Setaria glauca are not good enough.
Chinese patent CN201310273568.6 reports a series of has good bioactive compound, although Oryza sativa L. is had certain safety by part of compounds (CK) under low dosage (effective ingredient 8 grams/acre), safety to Oryza sativa L. under high dose is not described, when actual Field information, the effective ingredient consumption of 8 grams/acre cannot meet agricultural production requirement. And Oryza sativa L. is all had bigger poisoning by other structures related in patent. The safety of Oryza sativa L. is not enough far away. The structural formula of part of compounds is as follows:
German patent DE 2948095A1 discloses the following general formula compound that can be used for herbicide:
Wherein A can be(R can be halogen, and Y can be O, S etc.), X can be O, R2Can be H, R1Can being methyl, B can be chemical bond, R3Can being that H, E can for having the alkylidene of 1-3 carbon atom, G can be CN or COOR4(R4For H, the alkyl with 1-4 carbon atom).
Compound activity disclosed in patent is low (2.4kga.i./ha), and consumption is big, and does not report the safety to Oryza sativa L. in document. Proving through bioassay, part main compound is poor to the safety of Oryza sativa L., it is impossible to for rice terrace keeping from ill grass family weeding. The structural formula of part of compounds is as follows:
The present invention designs and has synthesized a series of novel compounds, and these compounds are better and Oryza sativa L. is safer to rice field malignant weed activity. The biological activity of its excellence and the safety of Oryza sativa L. height is different from prior art.
Summary of the invention
The present invention relates to the N-of the high herbicidal activity that new following formula (I) represents and replace alkyl virtue phenoxy base Propionamides compound and preparation and application thereof.
Technical scheme is as follows:
In formula:
R1Selected from hydrogen or C1-C6Alkane;
R3Selected from hydrogen or C1-C6Alkyl, C1-C6Haloalkyl, C3-C6Cycloalkyl, C2-C6Alkenyl, C2-C6Alkynyl group, C5-C12Aryl or heteroaryl;
Ar is selected from C6-C12Aryl, C5-C12Heterocyclic aryl, and hydrogen moiety in aryl, heterocyclic aryl or be all selected from following in identical or different substituent group replace: halogen, cyano group, nitro, C1-C6Alkyl, C1-C6Alkyl oxy, C1-C6Alkyl sulfenyl, C1-C6Alkyl amino, C1-C6Haloalkyl, C1-C6Halogenated alkoxy;
X is selected from N, O;
The chiral carbon atom of mark * is R or S configuration, or the mixture of R and S different proportion.
Currently preferred structural formula of compound is as follows:
R1Selected from hydrogen or methyl;
R3Selected from hydrogen or C1-C4Alkane, C2-C4Alkenyl;
Ar is selected from phenyl, C5-C6Heterocyclic aryl, and hydrogen moiety in phenyl, heterocyclic aryl or be all selected from following in identical or different substituent group replace: halogen, cyano group, nitro, C1-C3Alkyl, C1-C3Alkyl oxy, C1-C3Alkyl sulfenyl, C1-C3Alkyl amino, C1-C3Haloalkyl, C1-C3Halogenated alkoxy;
X is selected from N, O;
The chiral carbon atom of mark * is R or S configuration, or the mixture of R and S different proportion.
The structural formula of compound that the present invention is more highly preferred to is as follows:
R1Selected from hydrogen;
R3Selected from methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, the tert-butyl group;
Ar is selected from phenyl, pyridine radicals, thiazolyl, and the hydrogen atom in phenyl, pyridine radicals, thiazolyl can be replaced by following substituent group: fluorine, chlorine, bromine, methyl, methoxyl group, cyano group, nitro;
X is selected from O;
The chiral carbon atom of mark * is R configuration.
In compound given above (1) definition, also it is used in compound word no matter term used is used alone, represents following substituent group:
Halogen: refer to fluorine, chlorine, bromine, iodine;
Alkyl: refer to straight or branched alkyl;
Cycloalkyl: refer to saturated or undersaturated cycloalkyl;
Alkenyl: refer to straight or branched and double bond can be had on any position;
Alkynyl group: refer to straight or branched and three keys can be had on any position;
C6-C12Aryl means phenyl and by its derivative cyclophane base or polyaromatic;
C5-C12Refer to a ring heteroaryl or polyaromatic, structural formula has at least one or more N, O, S, P, such as pyridine radicals, pyrrole radicals, azoles base, isoxazole base etc.;
C6-C12Aryl and band can partly or entirely hydrogenate up to the heteroaryl of 10 carbon atoms, wherein 1 or 2 CH2Replaced by CO, such as cyclohexenyl group, cyclohexanedione base etc.
The general formula compound I of the present invention can be prepared by the following method:
Raw material II being dissolved in suitable solvent, and join in alkaline aqueous solution, temperature is-10 DEG C and reacts 1-24 hour between boiling point, then through hydrochloric acid or sulfuric acid acidation, prepares intermediate acid and Compound II per I.Suitable solvent selected from chloroform, dichloromethane, benzene, dioxane, oxolane, ethanol etc.; Suitable alkali is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate etc.
Compound shown in formula III reacts 1-24 hour with halide reagent such as thionyl chloride or oxalyl chloride, phosphorus oxychloride etc., obtains compound shown in Formulas I V. Suitable solvent selected from chloroform, dichloromethane, benzene, dioxane, oxolane, dichloroethanes, toluene etc.,
Intermediate compound IV is dissolved in suitable solvent, for instance chloroform, dichloromethane, benzene, toluene, oxolane, dichloroethanes, ethyl acetate, dioxane or in DMF, and add alkaloids, such as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate etc., temperature is-10 DEG C and reacts 1-24 hour between boiling point. Replace alkyl adding corresponding N-, be-10 DEG C then at temperature and react 1-24 hour between boiling point, prepare object I.
Can with table 1 below, in the compound listed the present invention is described, but do not limit the present invention.
Table 1: part the compounds of this invention as shown in formula I: X is O, R1For hydrogen.
The compound of Formula I of the present invention has activity of weeding, can be used for agriculturally preventing and kill off multiple weeds. Grassy weed can be effectively prevented and kill off as used after Seedling. With the Compound Phase ratio disclosed in prior art, the compounds of this invention broad weed-killing spectrum, superior activity. And to Oryza sativa L. high safety.
Present invention additionally comprises the herbicidal composition being active component with compound of Formula I. In said composition, the weight percentage of active component is 1-90%. This herbicidal composition also includes agriculturally acceptable carrier.
The example of the compositions of the present invention is wettable powder, cream, granule, aqueous suspension agent, oil-suspending agent etc. Generally using the compound dissolution of the present invention or be scattered in carrier to be configured to preparation so as herbicide use time more readily dispersible. Such as in these compositionss, at least add a kind of liquid or solid carrier, and typically require the surfactant that addition is suitable.
Present invention also offers the implementation of controlling weeds, the method includes on the surface of place or its somatomedin that the Herbicidal combinations of the present invention of herbicidally effective amount is suitable to described weeds or described weed growth. Comparatively suitable effective dose is per hectare 10 grams to 1000 grams, it is preferable that effective dose is that per hectare 10 to 500 grams, for some application, can add one or more other herbicides in the Herbicidal combinations of the present invention. Such as: cyhalofop-butyl, azoles acyl grass amine, fenoxaprop-P-ethyl, penoxsuam, butachlor, pretilachlor, Diflufenican, beflubutamid, benzobicylon, furan sulphur oxadiazon, ring sulphur ketone, mesotrione, fluorine ketone sulphur grass amine, fluroxypyr and bentazone etc.
The in some cases growth to crop mixed with some safener of the compound of Formula I of the present invention is useful. These safeners are selected from: fenchlorazole, double; two benzene azoles acid, cyclopropyl-sulfonylamide, mefenpyrdiethyl, meSnpyr aiethyl etc. The consumption of safener is per hectare 1 gram to 500 grams. The use of safener, can significantly improve the resistance of reverse of crop.
The compound of the present invention both can be used alone can also be known with other insecticide, antibacterial, plant growth regulator or fertilizer etc. mixes together.
It should be clear that in the patent requirements limited range of the present invention, it is possible to carry out various conversion and change.
Detailed description of the invention
Following example and raw result of the test of surveying can be used to further describe the present invention, but are not intended to limit the present invention. React raw materials used and reagent to be commercially available.
The preparation of embodiment 1 compound 1
(1) preparation of intermediate A
By 16.4 grams of ethyl phenylacetates, join in 250ml four-hole boiling flask, add 150ml dichloroethanes, 18 grams of bromines, the azodiisobutyronitrile of catalytic amount. Temperature rising reflux reacts 4 hours. React complete, deviate from solvent and namely obtain intermediate α Bromophenylacetic acid ethyl ester.
By 24.3 grams of α Bromophenylacetic acid ethyl esters, join in 250ml four-hole boiling flask, add 14.7 grams of phthalimides, 100 grams of N, dinethylformamide, stirred overnight at room temperature, reactant is poured in 250ml frozen water, filter, washing, solid is joined in the four-hole boiling flask of 250ml, add 150ml ethanol, heating for dissolving, drip hydrazine hydrate (36 grams, 80%), it is stirred at reflux under condition and reacts 3～4 hours, cooling, filtering, take filtrate, precipitation obtains 30 grams of A. of intermediate.
(2) preparation of compound 1
By 18 grams of intermediate A, join in 250ml four-hole boiling flask, add 100 grams of dichloroethanes, slowly instill 34 grams of acyl chlorides under room temperature, dropwise, be slowly added into 12 grams of triethylamines. Dropwise. It is stirred at room temperature 4 hours. Reacting complete, add 100ml water and stir 1 hour, layering, precipitation obtains 38 grams of solids.
δ ppm1.30 (t, 3H), 1.62 (d, 3H), 4.16-4.24 (m, 2H), 4.68-4.73 (m, 1H), 5.65-5,74 (m, 1H), 7.00 (t, 1H), 7.02 (s, 1H), 7.06-7.10 (m, 2H), 7.24-7.25 (m, 1H), 7.27-7.29 (m, 1H) 7.31-7.35 (m, 2H), 7.40-7.46 (m, 4H), white solid.
The preparation of embodiment 2 compound 9
(1) preparation of 2-(2-chloropyridine base) diethyl malonate
By 14.8 gram of 1,2-dichloropyridine, join in 250ml four-hole boiling flask, add 150mlN, dinethylformamide, 16 grams of diethyl malonates, 11 grams of potassium carbonate. 80 DEG C are reacted 4 hours. React complete, deviate from solvent, be about 3 with salt acid for adjusting pH. Obtain 23 grams of 2-of intermediate (2-chloropyridine base) diethyl malonate.
By 27 grams of 2-(2-chloropyridine base) diethyl malonate, join in 250ml four-hole boiling flask, add 100 grams of ethanol, 50 grams of water, add 20ml concentrated hydrochloric acid. Temperature rising reflux reacts 4 hours. React complete, deviate from solvent, obtain 15 grams of 2-(2-chloropyridine base) ethyl acetate.
The preparation method of 2-(2-chloropyridine base)-2-ethyl aminoacetate is from the preparation method of example 1 intermediate A.
The preparation method of compound 9 is from the preparation method of example 1 compound 1. δ ppm1.30 (t, 3H), 1.61 (d, 3H), 4.12-4.18 (m, 2H), 4.68-4.73 (m, 1H), 5.71-5,78 (m, 1H), 7.00 (t, 1H), 7.02 (s, 1H), 7.27-7.29 (m, 1H), 7.40-7.46 (m, 4H), 7.48-7.54 (m, 1H), 8.01-8.16 (m, 1H), 8.70-8.78 (m, 1H), white solid.
The preparation of embodiment 3 compound 12
(1) preparation of 2-chloropyridine acetonitrile
By 16.2 grams of 2-chloropyridine benzyl chlorine, 5.1 grams of Cyanogran .s, join in 250ml four-hole boiling flask, add 150ml ethanol, 11 grams of sodium carbonate. Temperature rising reflux, back flow reaction 4 hours. Reacting complete, deviate from ethanol, add 100 grams of water stirrings, namely sucking filtration obtains 21 grams of 2-chloropyridine acetonitriles.
(2) preparation of 2-chloropyridine ethyl acetate
15.2 grams of 2-chloropyridine acetonitriles are joined in 250ml four-hole boiling flask, adds 150ml ethanol, 10ml98% concentrated sulphuric acid, temperature rising reflux, back flow reaction 4 hours, reacts complete, deviates from ethanol, adds 100 grams of water stirrings, it is neutral for regulating pH with sodium carbonate, and sucking filtration obtains 2-chloropyridine ethyl acetate 13 grams.
The preparation method of 2-chloropyridine-2-ethyl aminoacetate is from the preparation method of example 1 intermediate A.
The preparation method of compound 12 is from the preparation method of example 1 compound 1. δ ppm1.30 (t, 3H), 1.61 (d, 3H), 4.12-4.18 (m, 2H), 4.68-4.73 (m, 1H), 5.68-5,76 (m, 1H), 7.00 (t, 1H), 7.02 (s, 1H), 7.22-7.25 (m, 1H), 7.40-7.46 (m, 4H), 7.74-7.78 (m, 1H), 8.10-8.21 (m, 1H), 8.80-8.95 (m, 1H), white solid.
Example 4 Herbicidal
Quantitative grassy weed (barnyard grass, Setaria glauca, Herba Digitariae, Semen Euphorbiae) seed is sowed at sectional area respectively is 100cm2Ceramic whiteware basin in, broadcast rear earthing 1cm, cultivate according to a conventional method in greenhouse after suppression, trickle. Grassy weed length is to 3～4 leaf phases. The Oryza sativa L. 3 leaf phase. By EXPERIMENTAL DESIGN dosage, carry out spraying process (atomisation pressure 1.95kg/cm2, spouting liquid 50ml/m2, crawler track speeds 30cm/s) with crawler type spraying machine (Britain EngineerResearchLtd. designs production). Examination material processes and is placed on handling hall, after medicinal liquid natural air drying, it is put in greenhouse and manages according to a conventional method, observe and record for the examination weeds reaction to medicament, and within latter 15 days, carry out range estimation investigation in processing, compare with the growing state of untreated control with the extent of injury of % injury record plant.
In test, plant is had good selectivity and weeds shows superior activity of weeding by formula (I) reactive compound. Partial test result is as follows:
Table 2
Test example 2 is to the activity of part elder weed and to Security of rice
Quantitative grassy weed (Setaria glauca, Herba Digitariae, Semen Euphorbiae) seed is sowed at sectional area respectively is 100cm2Ceramic whiteware basin in, broadcast rear earthing 1cm, cultivate according to a conventional method in greenhouse after suppression, trickle. Grassy weed length is to 6～8 leaf phases. The Oryza sativa L. 6 leaf phase. By EXPERIMENTAL DESIGN dosage. Examination material processes and is placed on handling hall, after medicinal liquid natural air drying, is put in greenhouse and manages according to a conventional method, observes and records for the examination weeds reaction to medicament, and within latter 20 days, carries out range estimation investigation in processing,
Table 3
Due to the development of Weed Resistance, there is new change in paddy field weed in recent years, and some multiresistance barnyard grasses are increasingly severe, in addition some upland weedses as: Setaria glauca, Herba Digitariae, Herba Eleusines Indicae etc. invade paddy field gradually. Current paddy field weed becomes increasingly complex. From data above it can be seen that Oryza sativa L. is not only had good safety by invention compound. And resistance barnyard grass, resistance Semen Euphorbiae and above the average age for marriage Setaria glauca that current rice terrace is occurred have good biological activity, are with a wide range of applications.

Claims (6)

1. N-replaces an alkyl phenoxy Propionamides compound, as shown in formula I:
In formula:
R1Selected from hydrogen or C1-C6Alkane;
R3Selected from hydrogen or C1-C6Alkyl, C1-C6Haloalkyl, C3-C6Cycloalkyl, C2-C6Alkenyl, C2-C6Alkynyl group, C5-C12Aryl or heteroaryl;
ArSelected from C6-C12Aryl, C5-C12Heterocyclic aryl, and hydrogen moiety in aryl, heterocyclic aryl or be all selected from following in identical or different substituent group replace: halogen, cyano group, nitro, C1-C6Alkyl, C1-C6Alkyl oxy, C1-C6Alkyl sulfenyl, C1-C6Alkyl amino, C1-C6Haloalkyl, C1-C6Halogenated alkoxy;
X is selected from N, O;
The chiral carbon atom of mark * is R or S configuration, or the mixture of R and S different proportion.
2. compound according to claim 1, it is characterised in that in formula I:
R1Selected from hydrogen or methyl;
R3Selected from hydrogen or C1-C4Alkane, C2-C4Alkenyl;
Ar is selected from phenyl, C5-C6Heterocyclic aryl, and hydrogen moiety in phenyl, heterocyclic aryl or be all selected from following in identical or different substituent group replace: halogen, cyano group, nitro, C1-C3Alkyl, C1-C3Alkyl oxy, C1-C3Alkyl sulfenyl, C1-C3Alkyl amino, C1-C3Haloalkyl, C1-C3Halogenated alkoxy;
X is selected from N, O;
The chiral carbon atom of mark * is R or S configuration, or the mixture of R and S different proportion.
3. compound according to claim 2, it is characterised in that in formula I:
R1Selected from hydrogen;
R3Selected from methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, the tert-butyl group;
Ar is selected from phenyl, pyridine radicals, thiazolyl, and the hydrogen atom in phenyl, pyridine radicals, thiazolyl can be replaced by following substituent group: fluorine, chlorine, bromine, methyl, methoxyl group, cyano group, nitro;
X is selected from O;
The chiral carbon atom of mark * is R configuration.
4. the compound described in claim 1 or 2 is for controlling the purposes of the pernicious grassy weed of rice terrace.
5. a Herbicidal combinations, it is characterised in that containing, for example the compound described in claim 1 or 2 and agriculturally acceptable carrier, in compositions, the weight percentage of active component is 1-99%.
6. a herbicidal composition as claimed in claim 5, it is characterised in that: insecticide that herbicidal composition can also be known with other, antibacterial, plant growth regulator or fertilizer, herbicide-safener mix together.
CN201610137493.2A 2016-03-11 2016-03-11 High-selectivity herbicide N-substitutive alkyl aryloxy phenoxyl propanamide compound and preparation and application thereof Pending CN105669584A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2948095A1 (en) * 1979-11-29 1981-06-19 Hoechst Ag, 6230 Frankfurt N-phenoxy-alkanoyl amino acid derivs. - useful as herbicides, fungicides and biocides
JPH0211580A (en) * 1988-06-30 1990-01-16 Kumiai Chem Ind Co Ltd Phenoxypropionic acid amide derivative and herbicide
CN101743219A (en) * 2007-07-03 2010-06-16 株式会社庆农 Optically active (R)-aryloxypropionic acid amides and herbicidal composition comprising same
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