CN101774979A - Class of aryl-acrylketone compound containing 1,3,5-dioxazine heterocycle, preparation method and application thereof - Google Patents

Class of aryl-acrylketone compound containing 1,3,5-dioxazine heterocycle, preparation method and application thereof Download PDF

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CN101774979A
CN101774979A CN201010100977A CN201010100977A CN101774979A CN 101774979 A CN101774979 A CN 101774979A CN 201010100977 A CN201010100977 A CN 201010100977A CN 201010100977 A CN201010100977 A CN 201010100977A CN 101774979 A CN101774979 A CN 101774979A
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oxadiazine
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sherwood oil
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凌云
杨绍祥
杨新玲
孙玉凤
孙亮
芦园园
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China Agricultural University
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China Agricultural University
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Abstract

The invention discloses a class of aryl-acrylketone compound (formula a) containing 1,3,5-dioxazine heterocycle, a preparation method and application thereof. The structural formula of the class of compound is shown as formula a in the specification, wherein, in formula a, Y is the formula showed in the specification, wherein R is H, F, Cl, Br, CH3O, C2H5O, 2,4-Cl2, NO2, CH3. In formula a, R1 is CH3, C2H5, and CH(CH3)2. The compound in the invention has simple structure and is easy to prepare. The compound in the invention has good activity on pests such as aphid, plutella xylostella, tetranychus cinnabarinus and the like, and the activity of the majority of the compound in the invention is superior to the effective components of natural Chinese stellera root, the invention can be applied practically in agricultural production.

Description

One class contains 1,3,5-oxadiazine heterocyclic arylprop ketene compounds and preparation method and application
Technical field
The present invention relates to a class and contain 1,3, the application in the control Agricultural pests of 5-oxadiazine heterocyclic arylprop ketene compounds and preparation method thereof and this compounds.
Background technology
Stellera chamaejasme L. (Stellera chamaejasme L.) is a thymelaeceae stellera plant, long ago people find that promptly the root of Stellera chamaejasme L. can be used for making biological pesticide-vegetable insecticide, have tag, stomach toxicity, effect such as stifling, can effectively prevent and treat cabbage caterpillar, aphid, eating-core bean worm, two-spotted spider mite, agrotis, loose high and steep moth, pine moth, pine sawfoy etc., but, and mainly concentrate on research to ethanol extraction to activeconstituents and indeterminate.People such as calendar year 2001 Liu Shigui use the normal hexane extraction Daphnetin first, isolate two kinds to the activated compound of aphid (E)-1 from Stellera chamaejasme L., 5-phenylbenzene-2-alkene-1-pentanone (I) and 1,5-phenylbenzene-1-pentanone (II).The indoor biometrics test shows that two compounds have stronger tagging and the food refusal effect to cotten aphid (Aphis gossypii) and green bugs (Schizaphis graminis).Tag in the test compound behind the 24h (I) and (II) to the LC of green bugs 50Be respectively 195 and 440mg/L, to the LC of cotten aphid 50Value is respectively 230 and 470mg/L; In the food refusal test, behind the 48h (I) and (II) when 1000mg/L the food refusal rate to cotten aphid (Aphis gossypii) be respectively 67.2% and 43.9%, food refusal rate to green bugs (Schizaphis graminis) is respectively 69.2% and 53.9% (Activity of the botanical aphicides 1,5-diphenyl-1-pentaone and1,5-diphenyl-2-penten-1-one on two species of Aphididnae.Pest Management Science, 2001,57 (3), 307-310.).
About Stellera chamaejasme L. effective constituent (I) and transformation (II), mainly contain 3 pieces of documents and 3 pieces of patent reports, people such as time peace simplify its synthetic difficulty by shortening carbochain; Perhaps the methods such as C atom that replace on the chain with heteroatomss such as O, N have been carried out some structural modifications (Synthesis and structure-activity study of botanicalaphicides 1 to it, 5-diphenyl-1-pentanone analogues.Pesticide Biochemistry andPhysiology, 2007,89:60-64.; Lead optimization and insecticidal activity ofanalogues of daphneolone isolated from Stellera chamaejasme L. Pest managementscience, 2007,63 (9), 928-34.; Lead optimization and anti-plant pathogenic fungiactivities of daphneolone analogues from Stellera chamaejasme L. PesticideBiochemistry and Physiology, 2009,93:133-137.), obtain the compound of a collection of structural modification, but do not introduce nitrogen heterocyclic ring.
The inventor had once carried out transforming (CN101402606 by the method for nitrogen heterocyclic ring and shortening carbochain in the introducing anabasine commodity medicament to structure; CN101423501; CN101423502), obtained a collection of certain bioactive compound that has.The present invention is when shortening carbochain, with 1,3, the method that the 1-phenyl that this important nitrogen heterocyclic ring of 5-oxadiazine substitutes natural lead compound carries out structure of modification still belongs to the first time, and obtained that a class can directly prevent eliminating aphis, the new compound of small cabbage moth and carmine spider mite.
Summary of the invention
One of purpose of the present invention is to disclose a class to contain 1,3,5-oxadiazine heterocyclic arylprop ketene compounds
Two of purpose of the present invention is the preparation methods that disclose above-mentioned analogue.
Three of the object of the invention be to disclose the above-mentioned compound of a class as directly anti-ly eliminate aphis, the application of small cabbage moth and carmine spider mite.
Provided by the present invention is that a class contains 1,3,5-oxadiazine heterocyclic arylprop ketene compounds, and its structural formula is formula a:
Figure GSA00000008638300021
Wherein, among the formula a, Y is:
Figure GSA00000008638300022
Wherein R is H, F, Cl, Br, OCH 3, OC 2H 5, 2,4-Cl 2, NO 2, CH 3
Among the formula a, R 1For: CH 3, C 2H 5, CH (CH 3) 2
Compound provided by the present invention can be prepared as follows:
Preparation method: furans acrylate chloride, thiophene acrylate chloride, substituted-phenyl acrylate chloride and the compound of structural formula shown in X in the presence of basic cpd, are carried out condensation reaction in organic solvent, obtain the compound shown in the formula a.
Its reaction equation is:
In the described method, be substituted aryl acrylate chloride and structural formula 10-50% suc as formula the compound total mass shown in the X as the consumption of the basic cpd of catalyzer.
In the described method, the compound of structural formula shown in X is the method preparation by document (ZL200410098491.4).
In the described method, described organic solvent comprises hydrocarbon or its halogenated product of aliphatics, alicyclic or aromatics: such as, benzene,toluene,xylene, chlorobenzene, dichlorobenzene, sherwood oil, hexane, hexanaphthene, methylene dichloride, chloroform, tetracol phenixin etc.; Ethers: as ether, diisopropyl ether, tetrahydrofuran (THF) or glycol dimethyl ether or ethylene glycol diethyl ether etc.; Ketone: as acetone, butanone or mibk etc.; Nitrile: as acetonitrile, propionitrile or butyronitrile etc.; Amides: as N, dinethylformamide, N,N-dimethylacetamide, N-methyl-formylaniline, N-Methyl pyrrolidone or HMPA etc.; Ester class: as methyl acetate or ethyl acetate etc.; Sulfoxide class: as dimethyl sulfoxide (DMSO); Alcohols: as methyl alcohol, ethanol, just-or Virahol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether etc. in one or more arbitrary combination.Described organic solvent is preferably toluene, benzene, second eyeball, sherwood oil and N, one or more arbitrary combination in the dinethylformamide.
Described basic cpd is organic bases or mineral alkali, is preferably one or more arbitrary combination in piperidines, sodium hydroxide, salt of wormwood, pyridine, triethylamine, yellow soda ash, sodium methylate and the sodium hydride etc.
Above-mentioned reaction can be carried out in wide relatively temperature range, and temperature of reaction can be-10 ℃ to 120 ℃, is preferably 20 ℃ to 100 ℃.
In the described method, comprise also reaction product is carried out chromatography purification that eluent is the V sherwood oil: V ethyl acetate=1: 1-10 is preferably the V sherwood oil: V ethyl acetate=1: 1-4.
With the The compounds of this invention be that activeconstituents anti-eliminates aphis, the medicine of small cabbage moth, carmine spider mite also belongs to protection scope of the present invention.In needs, can also add acceptable carrier in one or more pesticide preparation in described medicine, described carrier comprises thinner conventional in the pesticide preparation, vehicle, weighting agent, tackiness agent, wetting agent, absorption enhancer, tensio-active agent, lubricant, stablizer etc.The formulation of the medicine of making also is various, can be pulvis, emulsion, aqua, granule etc.
Compound of the present invention is on the basis of using for reference Stellera chamaejasme L. effective active composition active structure, introducing has the active group 4-nitro imino--1 of the anabasine pesticide that fine chemistry kills the aphid effect, 3, the 5-oxadiazine, the gained compound chemical structure is simple, to aphid, small cabbage moth, carmine spider mite activity well, in agriculture production, has practical value.
Compounds process for production thereof of the present invention, product purification method are simple, with low cost.
Experiment showed, that compound of the present invention has tangible biological activity, aphid, small cabbage moth, carmine spider mite are had direct chemical prevention effect, can be prepared as corresponding control agent.
Embodiment
The present invention can be described further with following examples, but the present invention is not limited in these embodiment, and the method among the following embodiment if no special instructions, is ordinary method.
The preparation of embodiment 1, (2E)-3-(2,4 dichloro benzene base)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone (YSX-18).
In the there-necked flask of 50mL, drop into 0.98g5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine, 1.5g piperidines and 15mL acetonitrile stir, and to the acetonitrile solution that wherein adds 1.20g 2,4 dichloro benzene base acrylate chloride, dropwise, in 40 ℃ of reaction 5h again.Reaction solution is cooled to room temperature, and solvent is sloughed in decompression, obtains red liquid.The product that to slough then behind the solvent directly carries out chromatographic separation, elutriant is the mixed solution (V: V=1: 1) of ethyl acetate and sherwood oil, the decompression precipitation, obtain white solid 0.75g, be (2E)-3-(2,4 dichloro benzene base)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-and acrylketone (YSX-18), productive rate 60.7%.Its 1H NMR spectrum data see Table 3.
Make other with method and contain 1,3,5-oxadiazine heterocyclic arylprop ketene compounds (seeing Table 1).
List formula a compound structure in the table-1 below, listed fusing point and yield in the table-2, listed the proton nmr spectra data in the table-3.
The structural formula and the chemical name of table-1 formula a compound
Compound number ??X ??Y Chemical name
??YSX-1 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine The 4-methoxyphenyl (2E)-3-(4-methoxyphenyl)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-2 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine The 4-bromophenyl (2E)-3-(4-bromophenyl)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-3 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine The 4-fluorophenyl (2E)-3-(4-fluorophenyl)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-4 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine The 3-aminomethyl phenyl (2E)-3-(3-aminomethyl phenyl)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-5 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine The 2,4 dichloro benzene base (2E)-3-(2,4 dichloro benzene base)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-6 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine Phenyl (2E)-3-phenyl-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-7 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine Thiophene-2-base (2E)-3-(thiophene-2-yl)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-8 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine Furans-2-base (2E)-3-(furans-2-yl)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
Compound number ??X ??Y Chemical name
??YSX-9 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine The 4-chloro-phenyl- (2E)-3-(4-chloro-phenyl-)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-10 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine The 4-ethoxyl phenenyl (2E)-3-(4-ethoxyl phenenyl)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-11 5-ethyl-4-nitro imino--1,3, the 5-oxadiazine The 4-nitrophenyl (2E)-3-(4-nitrophenyl)-1-(5-ethyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-12 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 The 4-ethoxyl phenenyl (2E)-3-(4-ethoxyl phenenyl)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-13 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 The 3-aminomethyl phenyl (2E)-3-(3-aminomethyl phenyl)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-14 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 The 4-bromophenyl (2E)-3-(4-bromophenyl)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-15 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 Thiophene-2-base (2E)-3-(thiophene-2-yl)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-16 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 Phenyl (2E)-3-phenyl-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
Compound number ??X ??Y Chemical name
??YSX-17 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 Furans-2-base (2E)-3-(furans-2-yl)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-18 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 The 2,4 dichloro benzene base (2E)-3-(2,4 dichloro benzene base)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-19 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 The 4-nitrophenyl (2E)-3-(4-nitrophenyl)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-20 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 The 4-chloro-phenyl- (2E)-3-(4-chloro-phenyl-)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-21 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 The 4-fluorophenyl (2E)-3-(4-fluorophenyl)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??YSX-22 5-sec.-propyl-4-nitro imino--1,3, the 5-oxadiazine 5 The 4-p-methoxy-phenyl (2E)-3-(4-p-methoxy-phenyl)-1-(5-sec.-propyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??A1 5-methyl-4-nitro imino--1,3, the 5-oxadiazine The 4-fluorophenyl (2E)-3-(4-fluorophenyl)-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
Compound number ??X ??Y Chemical name
??A2 5-methyl-4-nitro imino--1,3, the 5-oxadiazine The 4-chloro-phenyl- (2E)-3-(4-chloro-phenyl-)-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??A3 5-methyl-4-nitro imino--1,3, the 5-oxadiazine The 4-bromophenyl (2E)-3-(4-bromophenyl)-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??A4 5-methyl-4-nitro imido The 2,4 dichloro benzene base (2E)-3-(2,4 dichloro benzene base)-1-(5-methyl-4-nitro imino-
Base-1,3, the 5-oxadiazine -1,3,5-oxadiazine-3-yl)-acrylketone
??A5 5-methyl-4-nitro imino--1,3, the 5-oxadiazine The 4-nitrophenyl (2E)-3-(4-nitrophenyl)-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??A6 5-methyl-4-nitro imino--1,3, the 5-oxadiazine The 4-p-methoxy-phenyl (2E)-3-(4-p-methoxy-phenyl)-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??A7 5-methyl-4-nitro imino--1,3, the 5-oxadiazine The 4-ethoxyl phenenyl (2E)-3-(4-ethoxyl phenenyl)-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
Compound number ??X ??Y Chemical name
??A8 5-methyl-4-nitro imino--1,3, the 5-oxadiazine The 3-aminomethyl phenyl (2E)-3-(3-aminomethyl phenyl)-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??A9 5-methyl-4-nitro imino--1,3, the 5-oxadiazine The 3-phenyl (2E)-3-phenyl-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??A10 5-methyl-4-nitro imino--1,3, the 5-oxadiazine Furans-2-base (2E)-3-(furans-2-yl)-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
??A11 5-methyl-4-nitro imino--1,3, the 5-oxadiazine Thiophene-2-base (2E)-3-(thiophene-2-yl)-1-(5-methyl-4-nitro imino--1,3,5-oxadiazine-3-yl)-acrylketone
The fusing point and the yield of table-2 formula a compounds
Compound number Physical condition Purification process Fusing point (℃) Yield (%)
??YSX-1 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??142-144 ??17.2
??YSX-2 White solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??174-176 ??25.0
??YSX-3 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??169-170 ??31.5
??YSX-4 Yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??147-148 ??28.2
??YSX-5 White solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??139-140 ??45.5
??YSX-6 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??168-170 ??18.3
??YSX-7 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??165-167 ??15.2
??YSX-8 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??131-133 ??19.8
??YSX-9 White solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??172-174 ??22.4
??YSX-10 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??126-128 ??22.3
??YSX-11 Yellow solid Column chromatography (sherwood oil: ethyl acetate=3: 1) ??168-169 ??23.9
??YSX-12 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??162-164 ??47.4
??YSX-13 Yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??152-153 ??35.8
??YSX-14 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??166-168 ??34.6
??YSX-15 Brown solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??148-150 ??42.7
??YSX-16 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??136-138 ??32.8
??YSX-17 Brown solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??138-140 ??26.8
??YSX-18 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??154-156 ??60.7
??YSX-19 Brown solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??149-151 ??34.2
??YSX-20 Faint yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??155-157 ??30.2
Compound number Physical condition Purification process Fusing point (℃) Yield (%)
??YSX-21 White solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??131-132 ??45.5
??YSX-22 The khaki color solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??164-166 ??28.2
??A1 White crystal Column chromatography (sherwood oil: ethyl acetate=3: 1) ??110-112 ??71.4
??A2 White crystal Column chromatography (sherwood oil: ethyl acetate=2: 1) ??160-161 ??72.1
??A3 White crystal Column chromatography (sherwood oil: ethyl acetate=1: 1) ??148-150 ??69.0
??A4 White solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??180-181 ??73.0
??A5 Yellow solid Column chromatography (sherwood oil: ethyl acetate=1: 1) ??148-150 ??75.0
??A6 Pale yellow crystals Column chromatography (sherwood oil: ethyl acetate=4: 1) ??131-133 ??72.0
??A7 Light yellow solid Column chromatography (sherwood oil: ethyl acetate=2: 1) ??120-121 ??68.0
??A8 White crystal Column chromatography (sherwood oil: ethyl acetate=2: 1) ??100-102 ??67.0
??A9 White solid Column chromatography (sherwood oil: ethyl acetate=2: 1) ??120-121 ??71.0
??A10 Light yellow solid Column chromatography (sherwood oil: ethyl acetate=2: 1) ??113-115 ??56.0
??A11 Light yellow solid Column chromatography (sherwood oil: ethyl acetate=3: 1) ??106-108 ??76.0
The hydrogen spectrum data of table-3 formula a compounds
Compound number Proton nmr spectra, 1HNMR(δ，ppm)
??YSX-1 ??1.35(t，3H，J＝7.22Hz，C-CH 3)，3.67(q，2H，CH 2-C)，3.84(s，3H，O-CH 3)，??4.96(s，2H，O-CH 2-N)，5.36(s，2H，N-CH 2-O)，6.80-6.91(m，3H，＝CH-C＝O，Ar-2，6)，??7.51-7.54(q，2H，Ar-3，5)，7.83(ds，1H，J＝15.32Hz，CH＝C)
??YSX-2 ??1.36(t，3H，J＝7.20Hz，C-CH 3)，3.65-3.76(m，2H，CH 2-C)4.93(s，2H，O-CH 2-N)，??5.37(s，2H，N-CH 2-O)，6.94(ds，1H，J＝15.39Hz，＝CH-C＝O)，7.26-7.38??(m，2H，Ar-2，6)，7.48-7.52(m，2H，Ar-3，5)，7.80(ds，1H，J＝15.48Hz，CH＝C)
??YSX-3 ??1.35(t，3H，J＝7.23Hz，C-CH 3)，3.69(q，2H，CH 2-C)4.93(s，2H，O-CH 2-N)，??5.36(s，2H，N-CH 2-O)，6.90(dd，1H，J＝15.00Hz，＝CH-C＝O)，7.03-7.11??(m，2H，Ar-2，6)，7.53-7.59(m，2H，Ar-3，5)，7.81(ds，1H，J＝15.42Hz，CH＝C)
??YSX-4 ??1.33-1.37(q，3H，C-CH 3)，2.37(s，3H，Ar-CH 3)，3.64-3.76(m，2H，CH 2-C)，??4.92(s，2H，O-CH 2-N)，5.36(s，2H，N-CH 2-O)，6.93(ds，1H，J＝15.39Hz，＝CH-C＝O)，??7.20-7.23(m，1H，Ar-2)，7.24-7.30(m，1H，Ar-4)，??7.36-7.38(m，2H，Ar-5，6)，7.83(ds，1H，J＝15.48Hz，CH＝C)
??YSX-5 ??1.36(t，3H，J＝7.20Hz，C-CH 3)，3.65-3.76(m，2H，CH 2-C)，??4.93(s，2H，O-CH 2-N)，5.37(s，2H，N-CH 2-O)，6.94(ds，1H，J＝15.39Hz，＝CH-C＝O)，??7.24(d，1H，J＝8.52Hz，Ar-5)，7.43(d，1H，J＝2.07Hz，Ar-2)，??7.63(d，1H，J＝8.52Hz，Ar-4)，7.80(ds，1H，J＝15.48Hz，CH＝C)
Compound number Proton nmr spectra, 1HNMR(δ，ppm)
??YSX-6 ??1.35(t，3H，J＝7.26Hz，C-CH 3)，3.67(q，2H，CH 2-C)4.92(s，2H，O-CH 2-N)，??5.36(s，2H，N-CH 2-O)，6.96(ds，1H，J＝15.39Hz，＝CH-C＝O)，7.37-7.41??(m，3H，Ar-2，3，4)，7.55-7.58(m，2H，Ar-5，6)，7.86(ds，1H，J＝15.39Hz，CH＝C)
??1.35(t，3H，J＝7.22Hz，C-CH 3)，3.67(q，3H，CH 2-C)，4.92(s，2H，O-CH 2-N)，
??YSX-7 ??5.35(s，2H，N-CH 2-O)，6.74(ds，1H，J＝15.06Hz，＝CH-C＝O)，7.05-7.08??(q，1H，Thiophene-4)，7.34(d，1H，J＝3.41Hz，Thiophene-3)，??7.44(d，1H，J＝5.10Hz，Thiophene-5)，7.94(ds，1H，J＝15.09Hz，CH＝C)
??YSX-8 ??1.34(t，3H，J＝7.22Hz，C-CH 3)，3.67(q，3H，CH 2-C)，4.91(s，2H，O-CH 2-N)，??5.34(s，2H，N-CH 2-O)，6.47-6.49(m，1H，Fu-3)6.71(d，1H，J＝3.45Hz，Fu-4)，??6.82(ds，1H，J＝15.03Hz，＝CH-C＝O)，7.51(q，1H，Fu-5)，??7.59(ds，1H，J＝15.06Hz，CH＝C)
??YSX-9 ??1.26(t，3H，J＝7.20Hz，C-CH 3)，3.71(q，3H，CH 2-C)，4.93(s，2H，O-CH 2-N)，??5.37(s，2H，N-CH 2-O)，6.96(ds，1H，J＝15.39Hz，＝CH-C＝O)，??7.44(d，2H，J＝8.49Hz，Ar＝2，6)，7.52(d，2H，J＝8.55Hz，Ar＝3，5)??7.78(ds，1H，J＝15.48Hz，CH＝C)
Compound number Proton nmr spectra, 1HNMR(δ，ppm)
??YSX-10 ??1.35(t，3H，J＝7.22Hz，C-CH 3)，1.43(t，3H，J＝7.02Hz，O-C-CH 3)，??3.67(q，2H，CH 2-C)，4.06(q，2H，O-CH 2)，4.91(s，2H，O-CH 2-N)，??5.35(s，2H，N-CH 2-O)，6.80-6.89(m，3H，＝CH-C＝O，Ar＝2，6)，??7.49-7.52(m，2H，Ar＝3，5)，7.82(ds，1H，J＝15.36Hz，CH＝C)
??YSX-11 ??1.21(q，3H，C-CH 3)，3.58(d，2H，J＝7.14Hz，CH 2-C)，4.91(s，2H，O-CH 2-N)，??5.35(s，2H，N-CH 2-O)，6.76(d，1H，J＝16.08Hz，＝CH-C＝O)，??7，27(d，1H，J＝15.69Hz，CH＝C)，7.94-8.00(m，2H，Ar＝2，6)，??8.23-8.31(m，2H，Ar＝3，5)
??YSX-12 ??1.32(d，6H，J＝6.81Hz，C-(CH 3) 2)，1.42(t，3H，C-CH 3)，4.07(q，2H，CH 2-C)，??4.78(t，1H，CH-C 2)，4.84(s，2H，O-CH 2-N)，5.33(s，2H，N-CH 2-O)，??6.82(ds，1H，J＝15.30Hz，＝CH-C＝O)，6.88(d，2H，Ar＝2，6)，??7.51(d，2H，Ar＝3，5)，7.81(ds，1H，J＝15.33Hz，CH＝C)
??YSX-13 ??1.33(d，6H，J＝6.81Hz，C-(CH 3) 2)，2.37(s，3H，Ar-CH 3)，4.80(t，1H，CH-C 2)，??4.85(s，2H，O-CH 2-N)，5.34(s，2H，N-CH 2-O)，6.93(ds，1H，J＝15.39Hz，＝CH-C＝O)，??7.22-7.29(m，2H，Ar＝2，4)，7.36(s，2H，Ar＝5，6)，7.83(ds，1H，J＝15.39Hz，CH＝C)
??YSX-14 ??1.33(d，6H，J＝6.81Hz，C-(CH 3) 2)，4.79(t，1H，CH-C 2)，4.86(s，2H，O-CH 2-N)，??5.34(s，2H，N-CH 2-O)，6.95(ds，1H，J＝15.30Hz，＝CH-C＝O)，7.42(d，2H，Ar＝2，6)，??7.51(t，2H，Ar＝3，5)，7.78(ds，1H，J＝15.45Hz，CH＝C)
Compound number Proton nmr spectra, 1HNMR(δ，ppm)
??YSX-15 ??1.25(d，6H，J＝6.81Hz，C-(CH 3) 2)，4.55(t，1H，CH-C 2)，5.10(s，2H，O-CH 2-N)，??5.26(s，2H，N-CH 2-O)，6.73(ds，1H，J＝15.25Hz，＝CH-C＝O)，??7.15-7.18(q，1H，Thiophene-4)，7.57(d，1H，Thiophene-3)，7.57(d，1H，??Thiophene-5)，??7.85(ds，1H，J＝15.27Hz，CH＝C)
??YSX-16 ??1.33(d，6H，J＝6.81Hz，C-(CH 3) 2)，4.79(t，1H，CH-C 2)，4.86(s，2H，O-CH 2-N)，??5.34(s，2H，N-CH 2-O)，6.96(ds，1H，J＝15.39Hz，＝CH-C＝O)，??7.37-7.40(m，3H，Ar-2，3，4)，7.55-7.58(m，2H，Ar-5，6)，??7.86(ds，1H，J＝15.39Hz，CH＝C)
??1.25(d，6H，J＝6.81Hz，C-(CH 3) 2)，4.55(t，1H，CH-C 2)，5.10(s，2H，O-CH 2-N)，
??YSX-17 ??5.26(s，2H，N-CH 2-O)，6.65-6.67(q，1H，Fu-3)，??6.75(ds，1H，J＝15.31Hz，＝CH-C＝O)，7.00(d，1H，Fu-4)，??7.49(ds，1H，J＝15.30Hz，CH＝C)，7.89(d，1H，Fu-5)
??YSX-18 ??1.33(d，6H，J＝6.81Hz，C-(CH 3) 2)，4.78(t，1H，CH-C 2)，4.86(s，2H，O-CH 2-N)，??5.35(s，2H，N-CH 2-O)，6.93(ds，1H，J＝15.39Hz，＝CH-C＝O)，??7.25-7.28(m，1H，Ar＝5)，7.42(d，1H，Ar＝2)，7.63(d，1H，Ar＝4)，??8.17(ds，1H，J＝15.41Hz，CH＝C)
Compound number Proton nmr spectra, 1HNMR(δ，ppm)
??YSX-19 ??1.27(d，6H，J＝6.78Hz，C-(CH 3) 2)，4.58(t，1H，CH-C 2)，5.13(s，2H，O-CH 2-N)，??5.31(s，2H，N-CH 2-O)，7.27(ds，1H，J＝15.70Hz，＝CH-C＝O)，??7.26(ds，1H，J＝15.70Hz，CH＝C)，7.96(d，2H，J＝8.83Hz，Ar＝2，6)，??8.29(d，2H，J＝8.80Hz，Ar＝3，5)
??YSX-20 ??1.33(d，6H，J＝6.81Hz，C-(CH 3) 2)，4.78(t，1H，CH-C 2)，4.86(s，2H，O-CH 2-N)，??5.34(s，2H，N-CH 2-O)，6.93(ds，1H，J＝15.39Hz，＝CH-C＝O)，??7.34-7.36(q，2H，Ar＝2，6)，7.48-7.51(q，2H，Ar＝3，5)，??7.79(ds，1H，J＝15.42Hz，CH＝C)
??YSX-21 ??1.33(d，6H，J＝6.84Hz，C-(CH 3) 2)，4.79(t，1H，CH-C 2)，4.86(s，2H，O-CH 2-N)，??5.34(s，2H，N-CH 2-O)，6.89(ds，1H，J＝15.39Hz，＝CH-C＝O)，7.07(t，2H，Ar＝2，6)，??7.53-7.58(m，2H，Ar＝3，5)，7.82(ds，1H，J＝15.39Hz，CH＝C)
??YSX-22 ??1.33(d，6H，J＝6.81Hz，C-(CH 3) 2)，3.83(s，3H，O-CH 3)4.79(t，1H，CH-C 2)，??4.85(s，2H，O-CH 2-N)，5.33(s，2H，N-CH 2-O)，6.83(ds，1H，J＝15.30Hz，＝CH-C＝O)，??6.87-6.90(q，2H，Ar＝2，6)，7.51-7.54(q，2H，Ar＝3，5)，??7.83(ds，1H，J＝15.30Hz，CH＝C)
??A1 ??3.05(s，3H，N-CH 3)，5.10(s，2H，O-CH 2-N)，5.38(s，2H，N-CH 2-O)，7.01(d，??J＝15.57Hz，1H，＝CH-C＝O)，7.27～7.34(m，2H，Ar-2，6)，7.69(d，J＝15.63Hz，1H，??CH＝C)，7.73～7.80(m，2H，Ar-3，5)
Compound number Proton nmr spectra, 1HNMR(δ，ppm)
??A2 ??3.08(s，3H，N-CH 3)，5.11(s，2H，O-CH 2-N)，5.39(s，2H，N-CH 2-O)，7.07(d，??J＝15.62Hz，1H，＝CH-C＝O)，7.51～7.55(m，2H，Ar-2，6)，7.65～7.73(m，3H，Ar-3，5，??CH＝C)
??A3 ??3.08(s，3H，N-CH 3)，5.10(s，2H，O-CH 2-N)，5.38(s，2H，N-CH 2-O)，7.08(d，??J＝15.56Hz，1H，＝CH-C＝O)，7.62～7.68(m，5H，Ar-2，3，5，6，CH＝C)
??A4 ??3.08(s，3H，N-CH 3)，5.11(s，2H，O-CH 2-N)，5.39(s，2H，N-CH 2-O)，7.15(d，??J＝15.49Hz，1H，＝CH-C＝O)，7.58～7.59(m，1H，Ar-6)，7.77～7.86(m，3H，Ar-3，5，??CH＝C)
??A5 ??2.87(s，3H，N-CH 3)，4.88(s，2H，O-CH 2-N)，5.33(s，2H，N-CH 2-O)，7.64(d，??J＝15.84Hz，1H，＝CH-C＝O)，7.77(d，J＝15.84Hz，1H，CH＝C)，7.89～7.92(m，2H，??Ar-2，6)，8.26～8.28(m，2H，Ar-3，5)
??A6 ??3.07(s，3H，N-CH 3)，3.81(s，-OCH 3，)，5.09(s，2H，O-CH2-N)，5.36(s，2H，??N-CH 2-O)，6.89(d，J＝15.54Hz，1H，＝CH-C＝O)，6.99～7.02(d，J＝8.79Hz，2H，??Ar-2，6)，7.63～7.68(m，3H，Ar-3，5，CH＝C)
??A7 ??1.31～1.36(t，J＝8.62Hz，-CH 2CH 3，)，3.07(s，3H，N-CH 3)，4.05～4.12(t，J＝6.96Hz，??-CH 2CH 3，)，5.10(s，2H，O-CH 2-N)，5.36(s，2H，N-CH 2-O)，6.88(d，J＝15.46Hz，1H，??＝CH-C＝O)，6.97～7.01(m，2H，Ar-2，6)，7.60～7.68(m，3H，Ar-3，5，CH＝C)
Compound number Proton nmr spectra, 1HNMR(δ，ppm)
??A8 ??2.34(s，3H，CH3-Ar)，3.08(s，3H，N-CH3)，5.10(s，2H，O-CH 2-N)，5.38(s，2H，??N-CH 2-O)，7.25(d，J＝15.57Hz，1H，＝CH-C＝O)，7.26～7.50(m，4H，Ar-2，4，56)，??7.63(d，J＝15.54Hz，1H，CH＝C)
??A9 ??3.08(s，3H，N-CH 3)，5.10(s，2H，O-CH 2-N)，5.38(s，2H，N-CH 2-O)，7.05(d，??J＝15.64Hz，1H，＝CH-C＝O)，7.43～7.71(m，6H，Ar-2，3，4，5，6，CH＝C)
??A10 ??3.07(d，J＝2.69Hz，，3H，N-CH 3)，5.09(d，J＝1.70Hz，2H，O-CH 2-N)，5.33(d，??J＝1.11Hz，N-CH 2-O)，6.65～6.75(m，2H，Fu-4，＝CH-C＝O)，7.00～7.09(m，1H，??Fu-3)；7.44(d，J＝15.32Hz，1H，CH＝C)，7.89～7.90(t，J＝1.17Hz，1H，Fu-5)
??A11 ??3.07(s，3H，N-CH 3)，5.09(d，J＝2.51Hz，2H，O-CH 2-N)，5.34(s，2H，N-CH 2-O)，??6.72(d，J＝15.27Hz，1H，＝CH-C＝O)，7.15～7.18(m，1H，Thiophene-4)，??7.56～7.58(m，1H，Thiophene-3)，7.76～7.78(d，J＝5.07Hz，1H，Thiophene-5)，??7.87(d，J＝15.26Hz，1H，CH＝C)
Embodiment 2, The compounds of this invention are to the biological activity of aphid
With positive control medicament (E)-1,5-phenylbenzene-2-alkene-1-pentanone (I) and embodiment 1 gained compound sample use ten thousand/balance to take by weighing 12mg (folding hundred) compound sample in the 20ml weighing bottle respectively, get 2ml acetone/methanol (1: 1) mixed solvent with 1～5ml liquid-transfering gun again and add weighing bottle, after treating that it fully dissolves, adding 18ml contains the aqueous solution of 0.1% tween-80, abundant mixing, the mensuration liquid of 600 μ g/mL.Select tape aphid Leaf of Shrubalthea stays 3 ages in days if aphid will be with the aphid blade to flood 5s in soup, dries back record borer population and puts into the culture dish that is added with the filter paper of preserving moisture, and puts into (25 ± 1) ℃ illumination box after adding a cover.Each chemicals treatment is more than 30.Check result after 24 hours.Dead judging criterion is: touch polypide, the insect individuality that can not normally creep is considered as dead calculation correction mortality ratio.The result is shown in table-4, the result shows, under test concentrations, compound of the present invention has tangible lethal effect to aphid, part of compounds has significant lethal effect to aphid, and except compd A 1, A3, A4, A7, A8, A9, A10, A11, the corrected mortality of all the other compounds is all above lead compound (E)-1,5-phenylbenzene-2-alkene-1-pentanone (I) judges that tentatively this compounds is the novel aphid control agent with applications well prospect.
Table-4 formula a compounds are to the insecticidal activity of cotten aphid
Compound number Corrected mortality (%) Compound number Corrected mortality (%) Compound number Corrected mortality (%)
Natural product (I) ??70.1
??YSX-1 ??99.2 ??YSX-12 ??83.5 ??A1 ??42.1
??YSX-2 ??100 ??YSX-13 ??100 ??A2 ??85.0
??YSX-3 ??100 ??YSX-14 ??100 ??A3 ??61.4
??YSX-4 ??95.5 ??YSX-15 ??100 ??A4 ??67.5
??YSX-5 ??100 ??YSX-16 ??97.8 ??A5 ??85.1
??YSX-6 ??96.8 ??YSX-17 ??98.3 ??A6 ??75.0
??YSX-7 ??89.3 ??YSX-18 ??100 ??A7 ??59.3
??YSX-8 ??100 ??YSX-19 ??86.2 ??A8 ??57.6
??YSX-9 ??100 ??YSX-20 ??98.4 ??A9 ??19.7
??YSX-10 ??98.0 ??YSX-21 ??93.8 ??A10 ??62.7
??YSX-11 ??100 ??YSX-22 ??86.6 ??A11 ??25.8
Embodiment 3, The compounds of this invention are to the biological activity of small cabbage moth
With positive control medicament (E)-1,5-phenylbenzene-2-alkene-1-pentanone (I) and embodiment 1 gained compound sample are respectively with taking by weighing 12mg (folding hundred) compound sample with ten thousand/balance in the 20ml weighing bottle, use 1 ~ 5mL liquid-transfering gun to get 2mL acetone/methanol (1: 1) mixed solvent again and add weighing bottle, after treating that it fully dissolves, adding 18ml contains the aqueous solution of 0.1% tween-80, abundant mixing, the mensuration liquid of 600 μ g/mL.With method join pleocidin 10 μ g/mL.With the punch tool device clean cabbage leaves is broken into diameter 2cm leaf dish, in soup, flood 5s, dry posterior lobe and put into the diameter 6cm culture dish that is added with the filter paper of preserving moisture on dorsad, insert 10 of small cabbage moth 2 instar larvaes, put into (27 ± 1) ℃ illumination box after adding a cover.Check result after 72 hours.Dead judging criterion is: touch polypide, the insect individuality that can not normally creep is considered as death.The result is shown in table-5, and the result shows that under test concentrations, part of compounds of the present invention has tangible lethal effect to small cabbage moth, judges that tentatively this compounds has a good application prospect to small cabbage moth.
Table-5 formula a compounds are to the insecticidal activity of small cabbage moth
Compound number Corrected mortality (%) Compound number Corrected mortality (%) Compound number Corrected mortality (%)
Natural product (I) ??80.0
??YSX-1 ??10.0 ??YSX-12 ??30.0 ??A1 ??38.9
??YSX-2 ??0 ??YSX-13 ??0 ??A2 ??33.3
??YSX-3 ??30.0 ??YSX-14 ??70.0 ??A3 ??5.6
??YSX-4 ??80.0 ??YSX-15 ??20.0 ??A4 ??33.3
??YSX-5 ??0 ??YSX-16 ??70.0 ??A5 ??27.8
??YSX-6 ??40.0 ??YSX-17 ??100 ??A6 ??66.7
??YSX-7 ??30.0 ??YSX-18 ??50.0 ??A7 ??100
??YSX-8 ??50.0 ??YSX-19 ??60.0 ??A8 ??50.0
??YSX-9 ??40.0 ??YSX-20 ??40.0 ??A9 ??61.1
??YSX-10 ??20.0 ??YSX-21 ??40.0 ??A10 ??55.6
??YSX-11 ??10.0 ??YSX-22 ??40.0 ??A11 ??55.6
Embodiment 3, The compounds of this invention are to the biological activity assay of carmine spider mite
With positive control medicament (E)-1,5-phenylbenzene-2-alkene-1-pentanone (I) and embodiment 1 gained compound sample use ten thousand/balance to take by weighing 12mg (folding hundred) compound sample in the 20ml weighing bottle respectively, use 1 ~ 5ml liquid-transfering gun to get 2ml acetone/methanol (1: 1) mixed solvent again and add weighing bottle, after treating that it fully dissolves, adding 18ml contains the aqueous solution of 0.1% tween-80, abundant mixing, the mensuration liquid of 600 μ g/mL.The beans leaf of the carmine spider mite of having transferred is flooded 5s in soup, dry back record borer population and put into the culture dish that is added with the filter paper of preserving moisture, petiole is preserved moisture with the cotton of preserving moisture, and puts into (25 ± 1) ℃ illumination box after adding a cover.Each chemicals treatment is more than 20.Check result after 48 hours.Dead judging criterion is: touch polypide, the insect individuality that can not normally creep is considered as death.The result is shown in table-6, and the result shows that under test concentrations, part of compounds of the present invention has tangible lethal effect to carmine spider mite, judges that tentatively this compounds is the novel acarid control agent with applications well prospect.
Table-6 formula a compounds are to the insecticidal activity of carmine spider mite
Compound number Corrected mortality (%) Compound number Corrected mortality (%) Compound number Corrected mortality (%)
Natural product (I) ??25.4
??YSX-1 ??48.2 ??YSX-12 ??86.9 ??A1 ??44.1
??YSX-2 ??80.8 ??YSX-13 ??82.0 ??A2 ??38.9
??YSX-3 ??69.1 ??YSX-14 ??78.4 ??A3 ??70.3
??YSX-4 ??40.0 ??YSX-15 ??43.0 ??A4 ??23.8
??YSX-5 ??73.3 ??YSX-16 ??47.2 ??A5 ??72.5
??YSX-6 ??72.6 ??YSX-17 ??73.3 ??A6 ??17.2
??YSX-7 ??47.2 ??YSX-18 ??86.3 ??A7 ??44.7
??YSX-8 ??81.3 ??YSX-19 ??73.3 ??A8 ??56.0
??YSX-9 ??82.2 ??YSX-20 ??37.6 ??A9 ??15.2
??YSX-10 ??57.0 ??YSX-21 ??46.7 ??A10 ??17.4
??YSX-11 ??19.4 ??YSX-22 ??81.7 ??A11 ??47.56

Claims (10)

  1. Structural formula be formula a contain 1,3,5-oxadiazine heterocyclic arylprop ketene compounds.
    Figure FSA00000008638200011
    Wherein, among the formula a, Y is:
    Wherein R is H, F, Cl, Br, CH 3O, C 2H 5O, 2,4-Cl 2, NO 2, CH 3
    Among the formula a, R 1For: CH 3, C 2H 5, CH (CH 3) 2
  2. 2. the preparation method of the described compound of claim 1 is in the presence of basic cpd, in that the compound shown in X carries out condensation reaction by substituted aryl acrylate chloride and structural formula in the organic solvent, obtains the described compound of formula a.
  3. 3. method according to claim 2, it is characterized in that: described organic solvent is selected from benzene, toluene, dimethylbenzene, chlorobenzene, dichlorobenzene, sherwood oil, hexane, hexanaphthene, methylene dichloride, chloroform, tetracol phenixin, ether, diisopropyl ether, tetrahydrofuran (THF), glycol dimethyl ether, ethylene glycol diethyl ether, acetone, butanone, mibk, acetonitrile, propionitrile or butyronitrile, N, dinethylformamide, N, the N-N,N-DIMETHYLACETAMIDE, N-methyl-formylaniline, N-Methyl pyrrolidone or HMPA, methyl acetate, ethyl acetate, dimethyl sulfoxide (DMSO), methyl alcohol, ethanol, just-propyl alcohol, Virahol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, one or more arbitrary combination in the diethylene glycol monoethyl ether, be preferably toluene, butanone, benzene, N, dinethylformamide, acetonitrile or sherwood oil; Described organic solvents in particular is preferably toluene, N, dinethylformamide, acetonitrile, butanone; Described alkaline matter is selected from one or more arbitrary combination in piperidines, sodium hydroxide, salt of wormwood, pyridine, triethylamine, yellow soda ash, sodium methylate or the sodium hydride, is preferably pyridine, triethylamine, yellow soda ash.
  4. 4. method according to claim 2 is characterized in that: the temperature of described condensation reaction is-10 ℃-120 ℃; Be preferably 20 ℃-100 ℃.
  5. 5. method according to claim 2 is characterized in that: in the described method, comprise also reaction product is carried out chromatography purification that eluent is the V sherwood oil: V ethyl acetate=1: 1-10 is preferably the V sherwood oil: V ethyl acetate=1: 1-4.
  6. 6. the application of the described compound of claim 1 in control of aphids.
  7. 7. the application of the described compound of claim 1 in the carmine spider mite control.
  8. 8. the application of the described compound of claim 1 in the small cabbage moth control.
  9. 9. be the medicine of activeconstituents with the described compound of claim 1.
  10. 10. medicine according to claim 9 is characterized in that: described medicine be used for anti-eliminating aphis, the medicine of small cabbage moth, carmine spider mite.
CN201010100977A 2010-01-25 2010-01-25 Class of aryl-acrylketone compound containing 1,3,5-dioxazine heterocycle, preparation method and application thereof Pending CN101774979A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102241643A (en) * 2011-05-16 2011-11-16 中国农业大学 1-heterocycle-5-substituted phenyl-1-pentanone compound and preparation method and application thereof
CN107245060A (en) * 2017-06-29 2017-10-13 南通天泽化工有限公司 A kind of synthetic method of the oxadiazines of 3 acetyl 4 nitroimino 1,3,5
CN114668015A (en) * 2022-04-28 2022-06-28 华南农业大学 Application of oxadiazine cinnamamide compounds in preventing and treating plant diseases

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102241643A (en) * 2011-05-16 2011-11-16 中国农业大学 1-heterocycle-5-substituted phenyl-1-pentanone compound and preparation method and application thereof
CN107245060A (en) * 2017-06-29 2017-10-13 南通天泽化工有限公司 A kind of synthetic method of the oxadiazines of 3 acetyl 4 nitroimino 1,3,5
CN107245060B (en) * 2017-06-29 2020-08-04 南通天泽化工有限公司 Synthesis method of 3-acetyl-4-nitroimino-1, 3, 5-oxadiazine
CN114668015A (en) * 2022-04-28 2022-06-28 华南农业大学 Application of oxadiazine cinnamamide compounds in preventing and treating plant diseases
CN114668015B (en) * 2022-04-28 2023-09-19 华南农业大学 Application of oxadiazine cinnamamide compound in preventing and treating plant diseases

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