CN105859698A - N-(oxo-ethyl)-2-[4-(pyridine-2-yl-oxy)phenoxy]amide derivative - Google Patents

N-(oxo-ethyl)-2-[4-(pyridine-2-yl-oxy)phenoxy]amide derivative Download PDF

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CN105859698A
CN105859698A CN201610316886.XA CN201610316886A CN105859698A CN 105859698 A CN105859698 A CN 105859698A CN 201610316886 A CN201610316886 A CN 201610316886A CN 105859698 A CN105859698 A CN 105859698A
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oxoethyl
phenoxy group
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CN105859698B (en
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胡艾希
陈爱羽
李贝贝
杨子辉
李永红
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Hunan University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

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  • Agronomy & Crop Science (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention discloses a N-(oxo-ethyl)-2-[4-(pyridine-2-yl-oxy)phenoxy]amide derivative of a chemical structure formula I as shown in the specification, in the formula, R and R2 are selected from hydrogen, C1-C2 alkyl, C3-C4 linear alkyl or C3-C4 branched alkyl; R1 and R3 are selected from C1-C2 alkyl, C3-C4linear alkyl or C3-C4 branched alkyl; R1 and R3 are selected from C1-C2 alkyl, C3-C4 linear alkyl or C3-C4 branched alkyl; X1, X2, X4 and X6 are selected from hydrogen and C1-C2 alkyl; X3 is selected from hydrogen, C1-C2 alkyl, fluorine, chlorine, bromine or iodine; X5 is selected from hydrogen, C1-C2 alkyl, trifluoromethyl, fluorine, chlorine, bromine or iodine. The N-(oxo-ethyl)-2-[4-(pyridine-2-yl-oxy)phenoxy]amide derivative can be used for preparing herbicides.

Description

N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives
Technical field
The present invention relates to a class noval chemical compound and preparation method and application, specifically N-(oxoethyl)-2-[4-(pyridine-2- Base epoxide) phenoxy group] amide derivatives and in preparation method and application in preparing herbicide.
Background technology
4-aryloxyphenoxy acid derivative has biological activity widely, and wherein virtue phenoxy propanoic derivatives is as it Typical Representative, in agricultural herbicide existing more than 20 kind commercial varieties [DE2640730, DE3004770, US4713109, EP302203, JP54022371, EP4414, US 20030096706].4-aryloxyphenoxy carboxylic acid derivates is mainly made It is suppression Plant Acetyl-CoA Carboxylase by mode, thus affects the synthesis of vegetable fatty acid and then cause Plant death and reach To weeding purpose.Liu Changling etc. [CN 101747263B, 2012-1-11] are prepared for compound G, and it has good sterilization and lives Property, wherein under 400mg/L concentration, compound G1～G3 all reaches 100% to cucumber anthracnose preventive effect.
Liu prays magnitude [organic chemistry, 2014,34:118-125；SCI, 2014,35 (2): 262-26； CN20131008398.3,2014.8.6；CN201310274623.3,2015.1.14；CN201310273568.6,2015.1.14] With azoles acyl grass amine as lead compound, it is prepared for 2-(4-heteroaryl phenoxy base) propanoic derivatives.Wherein compound H1 pair Herba Digitariae and the IC of barnyard grass50Value (15.4g/ha and 22.8g/ha) is below azoles acyl grass amine (31.9g/ha and 25.0g/ha). Compound H2 is 100% to the inhibitory activity of Herba Digitariae, barnyard grass and Canis familiaris L. tail under the dosage of 2250g/ha.
The activity of weeding of N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives is not reported.
Summary of the invention
Present invention solves the technical problem that being to provide class N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide spreads out Biology, its preparation method, pesticide compositions and pesticide uses.
For solving the technical problem of the present invention, the present invention provides following technical scheme:
The first aspect of technical solution of the present invention is to provide N-(oxoethyl)-2-[4-(pyridine shown in a class chemical constitution Formulas I -2-base epoxide) phenoxy group] amide derivatives:
Wherein, R, R2It is selected from: hydrogen, C1～C2Alkyl, C3～C4Straight chained alkyl or C3～C4Branched alkyl；R1、R3Choosing From: C1～C2Alkyl, C3～C4Straight chained alkyl or C3～C4Branched alkyl；X1、X2、X4、X6It is selected from: hydrogen, C1～C2 Alkyl；X3It is selected from: hydrogen, C1～C2Alkyl, fluorine, chlorine, bromine or iodine；X5It is selected from: hydrogen, C1～C2Alkyl, trifluoromethyl, Fluorine, chlorine, bromine or iodine.
Further, preferred compound is selected from: (R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5- Base)-2-oxoethyl]-2-[4-(5-trifluoromethyl-3-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide., (R)-N-[2-(2,2-dimethyl -7-ethyoxyl-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl-3-chloropyridine-2-base epoxide) benzene oxygen Base] propionic acid amide., (R)-N-[2-(2,2-dimethyl-7-propoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-tri- Methyl fluoride-3-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide., (R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-dihydrobenzo furan Mutter-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl pyridine-2-base epoxide) phenoxy group] propionic acid amide., (R)-N-[2-(2,2-dimethyl -7-ethyoxyl-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl pyridine-2-base epoxide) phenoxy group] third Amide, (R)-N-[2-(2,2-dimethyl-7-propoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-fluoroform Yl pyridines-2-base epoxide) phenoxy group] propionic acid amide., (R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5- Base)-2-oxoethyl]-2-[4-(3-fluoro-5-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide., (R)-N-[2-(2,2-dimethyl-7-ethoxy Base-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(3-fluoro-5-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide., (R)-N-[2-(2,2-dimethyl-7-propoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(3-fluoro-5-chloropyridine-2- Base epoxide) phenoxy group] propionic acid amide..
The second aspect of technical solution of the present invention there is provided N-(oxoethyl)-2-[4-(pyridine-2-base described in first aspect Epoxide) phenoxy group] preparation method of amide derivatives, it is characterised in that preparation reaction is as follows:
Wherein, R, R2It is selected from: hydrogen, C1～C2Alkyl, C3～C4Straight chained alkyl or C3～C4Branched alkyl；R1、R3Choosing From: C1～C2Alkyl, C3～C4Straight chained alkyl or C3～C4Branched alkyl；X1、X2、X4、X6It is selected from: hydrogen, C1～C2 Alkyl；X3It is selected from: hydrogen, C1～C2Alkyl, fluorine, chlorine, bromine or iodine；X5It is selected from: hydrogen, C1～C2Alkyl, trifluoromethyl, Fluorine, chlorine, bromine or iodine.
The third aspect of technical solution of the present invention is to provide containing salt acceptable on compound described in first aspect and pesticide thereof Composition pesticide, this composition pesticide N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) benzene oxygen of the present invention containing effective dose Base] acceptable salt on amide derivatives and pesticide thereof, and optional containing pharmaceutical carrier.
The fourth aspect of technical solution of the present invention is to provide N-described in first aspect present invention (oxoethyl)-2-[4-(pyridine-2-base Epoxide) phenoxy group] on amide derivatives and pesticide thereof composition pesticide described in acceptable salt and the third aspect in preparation weeding Application in agent.
The present invention compared with prior art has the advantage that
Present invention discover that N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives has activity of weeding, can As preparing herbicide.
Detailed description of the invention
Following example are intended to illustrate rather than limitation of the invention further.
Embodiment 1
The preparation of 2-amino-1-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base) acetophenone hydrochloride (1a)
3.50g hexamethylenamine, 40mL chloroform, 45 DEG C of stirrings, drip 20ml 6.00g compound 2a chloroform Solution, TLC monitors, and reaction completely, is filtered, dried 7.40g white solid；7.40g white solid, 30mL Ethanol, 20.00g 36% hydrochloric acid, it is stirred at reflux 4.0h, filtered while hot, filtrate cools down, precipitation solid, filtration drying, Obtain 3.70g white solid 2-amino-1-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base) acetophenone hydrochloride 1a, Yield 58.6%, m.p.157～159 DEG C.1H NMR(CDCl3, 400MHz) and δ: 1.46 (s, 6H, 2 × CH3), 3.08 (s, 2H, ArCH2), 3.82 (s, 3H, OCH3), 4.51 (d, J=5.2Hz, 2H, COCH2), 7.40 (s, 1H, C6H24-H), 7.56 (s, 1H, C6H26-H), 8.17 (s, 2H, NH2)。
Embodiment 2
The preparation of 2-amino-1-(2,2-dimethyl-7-ethyoxyl-2,3-Dihydrobenzofuranes-5-base) acetophenone hydrochloride (1b)
Operate with embodiment 1, react 4.5h, obtain 3.00g white solid 2-amino-1-(2,2-dimethyl-7-ethyoxyl-2,3- Dihydrobenzofuranes-5-base) acetophenone hydrochloride 1b, yield 47.2%, m.p.220～223 DEG C.1H NMR(CDCl3, 500 MHz) δ: 1.34 (t, 3H, J=7.0Hz, CH3), 1.46 (s, 6H, 2 × CH3), 3.08 (s, 2H, ArCH2), 4.12 (q, 2H, J=7.0Hz, OCH2), 4.47 (d, J=4.5Hz, 2H, COCH2), 7.43 (s, 1H, C6H24-H), 7.58 (s, 1H, C6H24-H), 8.51 (s, 2H, NH2)。
Embodiment 3
The preparation of 2-amino-1-(2,2-dimethyl-7-propoxyl group-2,3-Dihydrobenzofuranes-5-base) acetophenone hydrochloride (1c)
Operate with embodiment 1, react 4.5h, obtain 3.03g white solid 2-amino-1-(2,2-dimethyl-7-propoxyl group-2,3- Dihydrobenzofuranes-5-base) acetophenone hydrochloride 1c, yield 52.9%, m.p.288～292 DEG C.1H NMR(CDCl3, 500 MHz) δ: 0.97 (t, 3H, J=7.0Hz, CH3), 1.46 (s, 6H, 2 × CH3), 1.70～1.77 (m, 2H, CH2CH3), 3.08 (s, 2H, ArCH2), 4.02 (t, 2H, J=7.0Hz, OCH2), 4.48 (d, J=5.5Hz, 2H, COCH2), 7.42 (s, 1H, C6H24-H), 7.58 (s, 1H, C6H26-H), 8.51 (s, 2H, NH2)。
Embodiment 4
(R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl -3-chloropyridine-2-base epoxide) phenoxy group] preparation of propionic acid amide.
0.55g 2-amino-1-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base) acetophenone hydrochloride 1a, 25mL Dichloromethane, 2mL triethylamine, under ice bath, dropping (R)-2-[4-(5-trifluoromethyl-3-chloropyridine-2-base epoxide) phenoxy group] Propionyl chloride dichloromethane solution；TLC monitoring reaction 1.5h, column chromatography for separation, obtain light yellow solid (R)-N-[2-(2,2- Dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl-3-chloropyridine-2-base oxygen Base) phenoxy group] propionic acid amide., yield 71.1%, m.p.146～149 DEG C, 1H NMR (CDCl3, 400MHz) and δ: 1.56 (s, 6H, 2 × CH3), 1.62 (d, J=6.8Hz, 3H, CH3), 3.09 (s, 2H, CH2), 3.92 (s, 3H, OCH3), 4.63～4.69 (m, 1H, CH), 4.74～4.80 (m, 2H, COCH2), 7.05 (d, J=8.8Hz, 2H, C6H42,6-H), 7.12 (d, J=8.8Hz, 2H, C6H43, 5-H), 7.42 (s, 1H, C6H24-H), 7.44 (s, 1H, C6H26-H), 7.62 (t, J=4.0Hz, 1H, NH), 7.97 (s, 1H, C5H2N 6-H), 8.26 (s, 1H, C5H2N 4-H)。
Embodiment 5
(R)-N-[2-(2,2-dimethyl-7-ethyoxyl-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-fluoroform Base-3-chloropyridine-2-base epoxide) phenoxy group] preparation of propionic acid amide.
Operate with embodiment 4, react 1.5h, obtain white solid (R)-N-[2-(2,2-dimethyl-7-ethyoxyl-2,3-dihydrobenzene And furan-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl-3-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide., yield 61.1%, m.p.123～125 DEG C, 1H NMR(CDCl3, 500MHz) and δ: 1.46 (t, J=7.0Hz, 3H, CH2CH3), 1.55 (s, 6H, 2 × CH3), 1.65 (d, J=6.5Hz, 3H, CH3), 3.07 (s, 2H, CH2), 4.13 (q, J=7.0Hz, 2H, OCH2), 4.62～4.67 (m, 1H, CH), 4.73～4.77 (m, 2H, COCH2), 7.04 (d, J=9.0Hz, 2H, C6H42,6-H), 7.12 (d, J=9.0 Hz, 2H, C6H43,5-H), 7.42 (s, 1H, C6H24-H), 7.44 (s, 1H, C6H26-H), 7.62 (t, J =4.0Hz, 1H, NH), 7.96 (d, J=1.5Hz, 1H, C5H3N 4-H), 8.25 (d, J=1.5Hz, 1H, C5H3N 6-H)。
Embodiment 6
(R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-fluoroform Yl pyridines-2-base epoxide) phenoxy group] preparation of propionic acid amide.
Operate with embodiment 4, react 1.0h, obtain yellow solid (R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-dihydrobenzene And furan-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl pyridine-2-base epoxide) phenoxy group] propionic acid amide., yield 67.9%, M.p.68～70 DEG C, 1H NMR(CDCl3, 500MHz) δ: 1.55 (s, 6H, 2 × CH3), 1.64 (d, J=6.5Hz, 3H, CH3), 3.08 (s, 2H, CH2), 3.91 (s, 3H, OCH3), 4.63～4.68 (m, 1H, CH), 4.73～4.78 (m, 2H, COCH2), 6.98 (d, J=8.5Hz, 1H, C5H3N 3-H), 7.03 (d, J=9.0Hz, 2H, C6H42,6-H), 7.09 (d, J=9.0Hz, 2H, C6H43,5-H), 7.41 (s, 1H, C6H24-H), 7.45 (s, 1H, C6H26-H), 7.60 (t, J=4.0Hz, 1H, NH), 7.87 (dd, J1=8.5Hz, J2=2.5Hz, 1H, C5H3N 4-H), 8.42 (d, J=2.5Hz, 1H, C5H3N 6-H)。
Embodiment 7
(R)-N-[2-(2,2-dimethyl-7-ethyoxyl-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-fluoroform Yl pyridines-2-base epoxide) phenoxy group] preparation of propionic acid amide.
Operate with embodiment 4, react 1.5h, obtain yellow solid (R)-N-[2-(2,2-dimethyl-7-ethyoxyl-2,3-dihydrobenzene And furan-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl pyridine-2-base epoxide) phenoxy group] propionic acid amide., yield 73.3%, M.p.129～132 DEG C, 1H NMR(CDCl3, 500MHz) δ: 1.46 (t, J=7.0Hz, 3H, CH2CH3), 1.55 (s, 6H, 2 × CH3), 1.65 (d, J=6.5Hz, 3H, CH3), 3.07 (s, 2H, CH2), 4.13 (q, J=7.0Hz, 2H, OCH2), 4.63～4.67 (m, 1H, CH), 4.73～4.77 (m, 2H, COCH2), 6.98～7.00 (m, 1H, C5H3N 3-H), 6.98 (d, J=8.5Hz, 1H, C5H3N 3-H).7.03 (d, J=9.0Hz, 2H, C6H42,6-H), 7.09 (d, J=9.0Hz, 2H, C6H43,5-H), 7.41 (s, 1H, C6H24-H), 7.44 (s, 1H, C6H26-H), 7.60 (t, J=4.0Hz, 1H, NH), 7.87～7.90 (m, 1H, C5H3N 4-H), 8.42 (d, J=3.5Hz, 1H, C5H3N 6-H)。
Embodiment 8
(R)-N-[2-(2,2-dimethyl-7-propoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-fluoroform Yl pyridines-2-base epoxide) phenoxy group] preparation of propionic acid amide.
Operate with embodiment 4, react 1.5h, obtain yellow solid (R)-N-[2-(2,2-dimethyl-7-propoxyl group-2,3-dihydrobenzene And furan-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl pyridine-2-base epoxide) phenoxy group] propionic acid amide., yield 64.7%, M.p.58～60 DEG C, 1H NMR(CDCl3, 500MHz) and δ: 1.41 (t, J =7.5Hz, 3H, CH2CH3), 1.55 (s, 6H, 2 × CH3), 1.65 (d, J=6.5Hz, 3H, CH3), 1.82～1.89 (m, 2H, CH2), 3.07 (s, 2H, ArCH2), 4.04 (t, J=7.0Hz, 2H, OCH2), 4.65～4.69 (m, 1H, CH), 4.74～4.79 (m, 2H, COCH2), 6.98 (d, J=6.0Hz, 1H, C5H3N 6-H), 7.04 (d, J=8.5Hz, 2H, C6H42,6-H), 7.10 (d, J=8.5Hz, 2H, C6H43,5-H), 7.42 (s, 1H, C6H24-H), 7.45 (s, 1H, C6H26-H), 7.69 (s, 1H, NH), 7.89 (d, J=8.5Hz, 1H, C5H3N 3-H), 8.43 (d, J=8.5Hz, 1H, C5H3N 4-H)。
Embodiment 9
(R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(3-fluoro-5-chlorine Pyridine-2-base epoxide) phenoxy group] preparation of propionic acid amide.
Operate with embodiment 4, react 1.0h, obtain faint yellow solid (R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-dihydro Benzofuran-5-base)-2-oxoethyl]-2-[4-(3-fluoro-5-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide., yield 62.8%, M.p.129～131 DEG C, 1H NMR(CDCl3, 500MHz) δ: 1.53 (s, 6H, 2 × CH3), 1.62 (d, J=6.5Hz, 3H, CHCH3), 3.07 (s, 2H, CH2), 3.90 (s, 3H, OCH3), 4.60～4.65 (m, 1H, CH), 4.71～4.77 (m, 2H, COCH2), 7.00 (d, J=9.5Hz, 2H, C6H42,6-H), 7.09 (d, J=9.5Hz, 2H, C6H43,5-H), 7.40 (s, 1H, C6H24-H), 7.44 (s, 1H, C6H26-H), 7.47 (dd, J1=9.0Hz, J2=2.5Hz, 1H, C5H2N 4-H), 7.59 (t, J=4.0Hz, 1H, NH), 7.84 (d, J=2.5Hz, 1H, C5H2N 6-H)。
Embodiment 10
(R)-N-[2-(2,2-dimethyl-7-ethyoxyl-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-fluoroform Yl pyridines-2-base epoxide) phenoxy group] preparation of propionic acid amide.
Operate with embodiment 4, react 1.0h, obtain light yellow solid (R)-N-[2-(2,2-dimethyl-7-ethyoxyl-2,3-dihydro Benzofuran-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl pyridine-2-base epoxide) phenoxy group] propionic acid amide., yield 70.2%, M.p.66～69 DEG C, 1H NMR(CDCl3, 400MHz) and δ: 1.44 (t, J =6.8Hz, 3H, CH2CH3), 1.53 (s, 6H, 2 × CH3), 1.62 (d, J=6.4Hz, 3H, CH3), 3.05 (s, 2H, CH2), 4.13 (q, J=6.8Hz, 2H, OCH2), 4.59～4.67 (m, 1H, CH), 4.71～4.77 (m, 2H, COCH2), 7.00 (d, J=9.2Hz, 2H, C6H42,6-H), 7.09 (d, J=9.2Hz, 2H, C6H43,5-H), 7.40 (s, 1H, C6H24-H), 7.42 (s, 1H, C6H26-H), 7.47 (dd, J1=9.2Hz, J2=2.0Hz, 1H, C5H3N 4-H), 7.61 (t, J=4.0Hz, 1H, NH), 8.42 (d, J=2.0Hz, 1H, C5H3N 6-H)。
Embodiment 11
The Herbicidal of N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives
1. target is barnyard grass (Echinochloa crus-galli) and Herba Digitariae (Digitaria sanguinalisL.Scop).
2. test medicine embodiment compound
3. the general sieve of experimental concentration sets single dose 100g/ mu.
4. test method
4.1 pot-culture methods (stem and leaf process): put into a certain amount of soil in the plastic cassettes of diameter 8cm, add a certain amount of water, After planting cover certain thickness soil, cultivate in greenhouse, cover with plastics before coming up.After emerging, every day is in addition Quantitative clear water is to keep normal growth.Carrying out stem and leaf spraying treatment when seedling grows to the regular period, treatment dosage is 1500g/ Hectare.Process 30 days " Invest, Then Investigate " results, measure overground part fresh weight, represent with fresh weight suppression percent.
4.2 pot-culture methods (soil treatment): put into a certain amount of soil in the plastic cassettes of diameter 8cm, add a certain amount of water, After planting cover certain thickness soil, cultivate in greenhouse, cover with plastics before coming up.Every day the most quantitative clear Water is to keep normal growth.Soil treatment, 1500g/ hectare is carried out before emerging.30 days " Invest, Then Investigate " results, measure overground part Fresh weight, represents drug effect with fresh weight suppression percent.
The most general sieve result is by living to the weeding of N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives The general sieve of property, dosage is 100g/ mu；General sieve and three compound primary dcreening operation results of selection list table 1 and 2 respectively in.
The activity of weeding of table 1 N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives
The activity of weeding primary dcreening operation result of table 2 N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives
N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives has good activity of weeding, can be as system The application of standby herbicide.

Claims (4)

1. N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives shown in a class chemical constitution formula I and acceptable salt on pesticide thereof:
Wherein, R, R2It is selected from: hydrogen, C1～C2Alkyl, C3～C4Straight chained alkyl or C3～C4Branched alkyl；R1、R3It is selected from: C1～C2Alkyl, C3～C4Straight chained alkyl or C3～C4Branched alkyl；X1、X2、X4、X6It is selected from: hydrogen, C1～C2Alkyl；X3It is selected from: hydrogen, C1～C2Alkyl, fluorine, chlorine, bromine or iodine；X5It is selected from: hydrogen, C1～C2Alkyl, trifluoromethyl, fluorine, chlorine, bromine or iodine.
2. acceptable salt on N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives described in claim 1 and pesticide thereof, it is characterised in that described compound is selected from:
(R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl-3-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide.,
(R)-N-[2-(2,2-dimethyl-7-ethyoxyl-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl-3-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide.,
(R)-N-[2-(2,2-dimethyl-7-propoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl-3-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide.,
(R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl pyridine-2-base epoxide) phenoxy group] propionic acid amide.,
(R)-N-[2-(2,2-dimethyl-7-ethyoxyl-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl pyridine-2-base epoxide) phenoxy group] propionic acid amide.,
(R)-N-[2-(2,2-dimethyl-7-propoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(5-trifluoromethyl pyridine-2-base epoxide) phenoxy group] propionic acid amide.,
(R)-N-[2-(2,2-dimethyl-7-methoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(3-fluoro-5-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide.,
(R)-N-[2-(2,2-dimethyl-7-ethyoxyl-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(3-fluoro-5-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide. or (R)-N-[2-(2,2-dimethyl-7-propoxyl group-2,3-Dihydrobenzofuranes-5-base)-2-oxoethyl]-2-[4-(3-fluoro-5-chloropyridine-2-base epoxide) phenoxy group] propionic acid amide..
3. the preparation method of N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives described in claim 1, it is characterised in that its preparation reaction is as follows:
Wherein, R, R1～R3、X1～X6Definition as claimed in claim 1.
4. on N-(oxoethyl)-2-[4-(pyridine-2-base epoxide) phenoxy group] amide derivatives described in claim 1 or 2 and pesticide thereof acceptable salt and pharmaceutical composition in preparation except the application in barnyard grass or Herba Digitariae herbicide.
CN201610316886.XA 2016-05-14 2016-05-14 N- (oxoethyl) -2- [4- (pyridine -2- bases epoxide) phenoxy group] amide derivatives Expired - Fee Related CN105859698B (en)

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