CN102190598A - Cyclopropane oxime ester derivatives and preparation method and application thereof - Google Patents
Cyclopropane oxime ester derivatives and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses cyclopropane oxime ester derivatives and a preparation method and application thereof. The cyclopropane oxime ester derivatives have a structural as a formula (I), wherein R1 refers to phenyl, furyl or substituted phenyl; R2 refers to hydrogen or cyan; a benzene ring of the substituted phenyl is subjected to monosubstitution or multi-substitution, and the substituent groups are respectively independently selected from C1-C10 alkyl, C1-C10 alkoxy, halogen and nitryl; and when the R2 refers to hydrogen, R1 does not refer to m-nitrophenyl. The cyclopropane oxime ester derivatives are easy to prepare, have excellent weeding activity and can be used as herbicides.
Description
(1) technical field
The present invention relates to a kind of cyclopropane oxime ester derivative and its production and use.
(2) background technology
The sixties, the pesticide species that contains the oxime structure often occurred at insecticidal/acaricidal agent, sterilant, weedicide, plant-growth regulator etc. so far.Wherein oxime ester compound has good desinsection, kills biological activitys such as mite, sterilization, weeding, Antiphytoviral, synergy, many kinds have efficiently, low toxicity, advantages such as low residue, oxime ester compound obtains comparatively extensive studies and uses the .20 sixties in century as a kind of pesticide activity, the insecticide variety that develops is mainly the oxime ester pesticides, as nitrogen base methylcarbamoyl oximino ester class, oxime phosphoric acid ester and have organophosphorus and the inferior prestige (U47319) of the sterilant phosphorus of oxime carbamate dual structure.Since the eighties in 20th century, the development of oximes agricultural chemicals has been developed large quantities of sterilant and weedicide rapidly successively.At present in novel pesticide initiative, has the molecular designing of the oximes structural compounds of effective active group, synthetic and bioactivity research remains one of focus.
Oxime ester pesticide activity also has (sulfo-) phosphoric acid oxime ester and carboxylic acid oxime ester based on oxime carbamate.
Carboxylic acid oxime ester has various active such as weeding, desinsection.Release the pyribenzoxim (pyribenzoxim) of RO-13-88950 and LG Corp of South Korea release as Maag agricultural chemicals company, pyribenzoxim as acetolactate synthestase (ALS) inhibitor is a selectivity ultra-high efficiency post-emergence herbicide, can effectively prevent and kill off multiple gramineous weeds and broadleaf weeds.
1999, Ma Junan etc. reported that with 4-diformazan (second) nitrogen benzaldehyde oxime ester be first guide structure, and the pyrethroid of selecting to have the triatomic ring structure (PY-acid) carries out structural modification, has synthesized a series of new oxime ester compounds (20).The anti-phytoviral activity The selection result shows: (20b) [(+)-suitable, anti--dibromo chrysanthemic acid-4-dimethylaminobenzaldehyde oxime ester] inhibiting rate to TMV when 250mg/L is the highest, reaches 60%, and secondly (20c), inhibiting rate is 30%.Test-results shows, compound (20b) is to all having higher biological activity and therapeutic action in various degree for examination virus, but antivirally infects active relatively lowly, can think tentatively that compound (20b) directly acts on virus and arrives therapeutic action.Afterwards, synthesized 6 novel pyrethroid lactazone acid derivatives (21) on this basis, biological assay shows that biological activity was the highest when phenyl ring 4 bit substituents replaced for the 4-dialkyl amido.But above-mentioned bibliographical information does not all relate to the action effect of prepared derivative aspect weeding.
(3) summary of the invention
The primary technical problem that the present invention will solve is to provide a kind of cyclopropane oxime ester compound, and it has excellent weeding activity.
Cyclopropane oxime ester derivative of the present invention, its structure is suc as formula shown in (I):
R wherein
1Represent phenyl, furyl or substituted-phenyl, R
2Represent hydrogen or cyano group; Be single replace or polysubstituted on the phenyl ring of described substituted-phenyl, it is one of following that described substituting group independently is selected from separately: the alkyl of C1～C10, the alkoxyl group of C1～C10, halogen, nitro; And work as R
2When representing hydrogen, R
1Do not represent the m-nitro base.
Further, in the described substituted-phenyl, it is one of following that described substituting group independently is selected from separately: the alkyl of C1～C3, the alkoxyl group of C1～C3, chlorine, bromine, nitro.
Further, R
1Represent one of following: phenyl, furyl, o-tolyl, p-methylphenyl, to bromophenyl, m-nitro base, 2,4 dichloro benzene base, p-methoxyphenyl, ortho-nitrophenyl base, 3,4-Dimethoxyphenyl, rubigan.
The described R of the concrete recommendation of the present invention
1And R
2Combination be selected from one of a～j:
A:R
1=o-tolyl, R
2=H; B:R
1=p-methylphenyl, R
2=H; C:R
1=to bromophenyl, R
2=H; D:R
1=2,4 dichloro benzene base, R
2=H; E:R
1=phenyl, R
2=CN; F:R
1=p-methoxyphenyl, R
2=H; G:R
1=ortho-nitrophenyl base, R
2=H; H:R
1=furyl, R
2=H; I:R
1=3,4-Dimethoxyphenyl, R
2=H; J:R
1=rubigan, R
2=H.
Second technical problem that the present invention will solve provides a kind of preparation method of described cyclopropane oxime ester derivative.
For solving the problems of the technologies described above, the present invention adopts following technical scheme:
A kind of preparation method of described cyclopropane oxime ester derivative, described preparation method is: the cyclopropyl formyl chloride shown in replacement oxime shown in the formula (IV) and the formula (III), in polar aprotic solvent, in the presence of acid binding agent, react, make described cyclopropane oxime ester derivative;
In the formula (IV), R
1, R
2Definition cotype (I).
Further, described polar aprotic solvent is preferably 1,4-dioxane, acetonitrile or tetrahydrofuran (THF).The quality consumption of organic solvent is generally 20-50 times of cyclopropyl formyl chloride quality.
Further, the preferred triethylamine of described acid binding agent.
Further, the molar ratio of described replacement oxime and cyclopropyl formyl chloride is preferably 1: 1-1.1.The molar ratio of described replacement oxime and acid binding agent is preferably 1: 0.05～and 0.2.
Further, described reaction is preferably at room temperature carried out.
The present invention can use ordinary method monitoring reaction terminal point, and as monitoring with TLC, the reaction times was generally 2-5 hour.
The preparation method of cyclopropane oxime ester derivative of the present invention, after reacting completely, the gained reaction solution can obtain final product through conventional aftertreatment, described aftertreatment can be: after reacting completely, wash with 10% sodium bicarbonate aqueous solution, be washed with water to neutrality, separate organic phase, anhydrous MgSO
4Drying is filtered, and precipitation obtains thick product, recrystallization or column chromatography.Column chromatography or recrystallization solvent for use can be sherwood oil, ethyl acetate, normal hexane, ethanol or their mixed solution.
Cyclopropyl formyl chloride of the present invention can be via cyclopropane-carboxylic acid and suitable chlorination reagent (such as SOCl
2) reaction make.Therefore, reaction equation can be expressed as follows:
The 3rd technical problem that the present invention will solve provides the purposes of described cyclopropane oxime ester derivative as weedicide.
All compounds are under the using dosage of 100ppm and 10ppm among the present invention, and to broadleaf weed such as rape, monocotyledons such as barnyard grass grass have medium inhibition activity on the upper side, so can be as the weedicide in field.
Compared with prior art, beneficial effect of the present invention is: the invention provides the new oxime ester derivative of a class, this oxime ester derivative preparation is simple, has excellent weeding activity.
(4) specific implementation method
Substantive distinguishing features of the present invention can be achieved from following embodiment, but these embodiment only as an illustration, rather than limits the invention.
The preparation of embodiment 1, compound 3a
In 50mL four-hole round-bottomed bottle, add 3.5mmol o-methyl-benzene formoxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride that is dissolved with 0.68g (4.2mmol), finish stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3a.The yield of compound 3a, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2.
The preparation of embodiment 2 compound 3b
In 50mL four-hole round-bottomed bottle, add 3.5mmol p-tolyl aldehyde oxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride that is dissolved with 0.68g (4.2mmol), finish stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3b.The yield of compound 3b, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2.
The preparation of embodiment 3 compound 3c
In 50mL four-hole round-bottomed bottle, add 3.5mmol p-bromobenzaldehyde oxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride that is dissolved with 0.68g (4.2mmol), finish stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3c.The yield of compound 3c, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2
The preparation of embodiment 5 compound 3d
In 50mL four-hole round-bottomed bottle, add 3.5mmol 2, the 4-dichloro benzaldoxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride be dissolved with 0.68g (4.2mmol), finish, stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3d.The yield of compound 3d, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2.
The preparation of embodiment 6 compound 3e
In 50mL four-hole round-bottomed bottle, add 3.5mmol alpha-cyano benzaldoxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride that is dissolved with 0.68g (4.2mmol), finish stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3e.The yield of compound 3e, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2.
The preparation of embodiment 7 compound 3f
In 50mL four-hole round-bottomed bottle, add 3.5mmol aubepine oxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride that is dissolved with 0.68g (4.2mmol), finish stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3f.The yield of compound 3f, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2.
The preparation of embodiment 8 compound 3g
In 50mL four-hole round-bottomed bottle, add 3.5mmol Ortho Nitro Benzaldehyde oxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride that is dissolved with 0.68g (4.2mmol), finish stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3g.The yield of compound 3g, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2.
The preparation of embodiment 9 compound 3h
In 50mL four-hole round-bottomed bottle, add 3.5mmol 3,4-dimethoxy benzaldehyde oxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride be dissolved with 0.68g (4.2mmol), finish, stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3h.The yield of compound 3h, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2.
The preparation of embodiment 10 compound 3i
In 50mL four-hole round-bottomed bottle, add 3.5mmol furtural oxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride that is dissolved with 0.68g (4.2mmol), finish stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3i.The yield of compound 3i, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2.
The preparation of embodiment 11 compound 3j
In 50mL four-hole round-bottomed bottle, add 3.5mmol 4-chloro-benzaldehyde oxime, 0.43g triethylamine (4.2mmol), among the 10mL THF, be cooled to below 5 ℃, slowly drip the 5mL THF solution of the cyclopropyl formyl chloride that is dissolved with 0.68g (4.2mmol), finish stirring at room to aldoxime react completely (TLC monitoring).After reacting completely,, be washed with water to neutrality, separate organic phase, anhydrous MgSO with the washing of 10% sodium bicarbonate aqueous solution
4Drying is filtered, and precipitation obtains thick product, uses the sherwood oil recrystallization, obtains compound 3j.The yield of compound 3j, physico-chemical constant and results of elemental analyses see Table 1, MS and
1H NMR data see Table 2.
Physico-chemical constant and the ultimate analysis of table 1 compound 3a-3j
The MS of table 2 compound 3a-3j and
1H NMR data
Embodiment 12 biological activity tests
Weeding vitro test method (in vitro)
The Bacillus coli cells that utilizes recombinant plasmid (containing paddy rice KARI enzyme gene) to transform is expressed paddy rice KARI enzyme in enormous quantities, the interaction of research organic molecule and KARI enzyme under the condition that exsomatizes.Reaction adopts dynamic method to carry out the reduction of the characteristic absorbance of continuous monitoring NADPH (340nm).Comprise 0.1molL in the reaction system
-1Phosphoric acid buffer (pH=8.0) 900uL, 0.2mmolL
-1NADPH 10uL, 1mmolL
-1MgCl
210uL, 0.1mmolL
-1Acetylactis 10uL adds the solution 10uL and the KARI zymoprotein 20uL of the prepared water-soluble acquisition of cyclopropane oxime ester derivative of the embodiment of the present application 1 of concentration 100ppm.Before the reaction various compositions (except the acetylactis) are joined in the disposable cuvette, in 340nm place (30 ℃), begin test with spectrophotometer, behind the 10min, add 10uL acetylactis solution, continue test 340nm place light absorption value (this moment, the absorbancy of 340nm began to descend gradually) fast behind the mixing immediately, thereby obtain the activity inhibition curve of cyclopropane oxime ester derivative to the KARI enzyme, calculate inhibiting rate thereby do contrast with blank enzyme, the result is as shown in table 3.
Remove cursive script build-in test method (in vivo)
The rape Plating
Complete the filter paper of a diameter 5.6cm in the culture dish of diameter 6cm, add 2 milliliters of certain density test compound solution, 10 of 4 hours Semen Brassicae campestriss of sowing seed soaking.Under 28 ± 1 ℃, dark culturing was measured radicle length after 72 hours.The growth-inhibiting of rape radicle is come the weeding activity of detection compound by compound under the dark condition.Test concentrations: 10 μ g/mL and 100 μ g/mL.Each is handled and repeats twice.Activity index: radicle elongation inhibiting rate (%) the results are shown in Table 3.Active graded index: A level: 〉=80%; B level: 60～79%; C level: 40～59%; D level :≤39%.
The little agar diffusion method of barnyard grass grass
After completing granulated glass sphere and filter paper in 50 milliliters the small beaker, add 6 milliliters of certain density test compound solution, 10 of the barnyard grass grass seeds that sowing has just showed money or valuables one carries unintentionally.Under 28 ± 1 ℃, illumination cultivation is measured the height of seedling after 72 hours.By compound under the illumination condition growth-inhibiting of barnyard grass grass seedling plant height is come the weeding activity of detection compound.Test concentrations: 10 μ g/mL and 100 μ g/mL.Each is handled and repeats twice.Activity index: plant height growth inhibition ratio (%) the results are shown in Table 3.Active graded index: A level: 〉=80%; B level: 60～79%; C level: 40～59%; D level :≤39%.
Test result sees Table 1.
Active and the weeding activity (growth-inhibiting %) of the KARI of table 3 compound 3a-3j
-: the not dissolving of expression sample, not test.
Claims (10)
1. cyclopropane oxime ester derivative, its structure is suc as formula shown in (I):
R wherein
1Represent phenyl, furyl or substituted-phenyl, R
2Represent hydrogen or cyano group; Be single replace or polysubstituted on the phenyl ring of described substituted-phenyl, it is one of following that described substituting group independently is selected from separately: the alkyl of C1～C10, the alkoxyl group of C1～C10, halogen, nitro; And work as R
2When representing hydrogen, R
1Do not represent the m-nitro base.
2. cyclopropane oxime ester derivative as claimed in claim 1 is characterized in that: described substituting group independently is selected from one of following separately: the alkyl of C1～C3, the alkoxyl group of C1～C3, chlorine, bromine, nitro.
3. cyclopropane oxime ester derivative as claimed in claim 1 is characterized in that: R
1Represent one of following: phenyl, furyl, o-tolyl, p-methylphenyl, to bromophenyl, m-nitro base, 2,4 dichloro benzene base, p-methoxyphenyl, ortho-nitrophenyl base, 3,4-Dimethoxyphenyl, rubigan.
4. cyclopropane oxime ester derivative as claimed in claim 1 is characterized in that described R
1And R
2Combination be selected from one of a～j:
A:R
1=o-tolyl, R
2=H; B:R
1=p-methylphenyl, R
2=H; C:R
1=to bromophenyl, R
2=H; D:R
1=2,4 dichloro benzene base, R
2=H; E:R
1=phenyl, R
2=CN; F:R
1=p-methoxyphenyl, R
2=H; G:R
1=ortho-nitrophenyl base, R
2=H; H:R
1=furyl, R
2=H; I:R
1=3,4-Dimethoxyphenyl, R
2=H; J:R
1=rubigan, R
2=H.
5. the preparation method of a cyclopropane oxime ester derivative as claimed in claim 1, it is characterized in that described preparation method is: the cyclopropyl formyl chloride shown in replacement oxime shown in the formula (IV) and the formula (III), in polar aprotic solvent, in the presence of acid binding agent, react, make described cyclopropane oxime ester derivative;
In the formula (IV), R
1, R
2Definition cotype (I).
6. the preparation method of cyclopropane oxime ester derivative as claimed in claim 5 is characterized in that described polar aprotic solvent is 1,4-dioxane, acetonitrile or tetrahydrofuran (THF).
7. the preparation method of cyclopropane oxime ester derivative as claimed in claim 5 is characterized in that described acid binding agent is a triethylamine.
8. the preparation method of cyclopropane oxime ester derivative as claimed in claim 5 is characterized in that described reaction at room temperature carries out.
9. the preparation method of cyclopropane oxime ester derivative as claimed in claim 5, the molar ratio that it is characterized in that described replacement oxime and cyclopropyl formyl chloride, acid binding agent is 1: 1-1.1: 0.05-0.2.
10. cyclopropane oxime ester derivative as claimed in claim 1 is as the purposes of weedicide.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106146350A (en) * | 2016-07-21 | 2016-11-23 | 华南理工大学 | A kind of new method of synthesizing amino methylcarbamoyl oximino ester derivant |
| CN107954898A (en) * | 2017-12-01 | 2018-04-24 | 西北农林科技大学 | Salicylaldoxime ester type compound and preparation method thereof, purposes |
| CN110551098A (en) * | 2019-06-17 | 2019-12-10 | 湖北固润科技股份有限公司 | oxime ester photoinitiator containing five-membered aromatic heterocyclic structure and preparation and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644524A (en) * | 1967-11-30 | 1972-02-22 | Gulf Research Development Co | Combating weeds with o-acyl-3 5-dialkyl-4-hydroxybenzaldoximes |
| BE810266R (en) * | 1973-12-14 | 1974-07-29 | 6- (ALPHA- (AMIDINO- AND IMIDOYLAMINOALCANOYLAMINO) -ARACYLAMINO) PENICILLANIC ACIDS AND THEIR PREPARATION | |
| JP2004035439A (en) * | 2002-07-02 | 2004-02-05 | Sankyo Agro Kk | Nicotinamide derivative |
| WO2007145888A2 (en) * | 2006-06-05 | 2007-12-21 | The Feinstein Institute For Medical Research | Oxime derivatives as inhibitors of macrophage migration inhibitory factor |
| WO2009086303A2 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
-
2011
- 2011-03-28 CN CN201110075018.4A patent/CN102190598B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644524A (en) * | 1967-11-30 | 1972-02-22 | Gulf Research Development Co | Combating weeds with o-acyl-3 5-dialkyl-4-hydroxybenzaldoximes |
| BE810266R (en) * | 1973-12-14 | 1974-07-29 | 6- (ALPHA- (AMIDINO- AND IMIDOYLAMINOALCANOYLAMINO) -ARACYLAMINO) PENICILLANIC ACIDS AND THEIR PREPARATION | |
| JP2004035439A (en) * | 2002-07-02 | 2004-02-05 | Sankyo Agro Kk | Nicotinamide derivative |
| WO2007145888A2 (en) * | 2006-06-05 | 2007-12-21 | The Feinstein Institute For Medical Research | Oxime derivatives as inhibitors of macrophage migration inhibitory factor |
| WO2009086303A2 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
Non-Patent Citations (8)
| Title |
|---|
| 《农药学学报》 19990815 马军安等 取代苯甲醛肟羧酸酯的合成及生物活性研究(IV)__拟除虫菊酸4-二甲(乙)氨基苯甲醛肟酯的合成及生物活性 8-13 1-10 第01卷, 第03期 * |
| 《应用化学》 19980220 黄润秋等 取代苯甲醛肟羧酸酯的合成及生物活性研究--Ⅰ.取代苯甲醛肟二氯菊酸酯的合成及生物活性 9-12 1-10 第15卷, 第01期 * |
| 《应用化学》 20020225 马军安等 取代苯甲醛肟羧酸酯的合成及生物活性研究 Ⅵ.4-二甲氨基苯甲醛肟酯的合成及生物活性 176-178 1-10 第19卷, 第02期 * |
| 《高等学校化学学报》 19990515 马军安等 取代苯甲醛肟羧酸酯的合成及生物活性研究 (Ⅲ)--取代苯甲醛肟四甲基环丙烷羧酸酯的合成及生物活性 747-749 1-10 第20卷, 第05期 * |
| 马军安等: "取代苯甲醛肟羧酸酯的合成及生物活性研究 (Ⅲ)──取代苯甲醛肟四甲基环丙烷羧酸酯的合成及生物活性", 《高等学校化学学报》, vol. 20, no. 05, 15 May 1999 (1999-05-15), pages 747 - 749 * |
| 马军安等: "取代苯甲醛肟羧酸酯的合成及生物活性研究 Ⅵ.4-二甲氨基苯甲醛肟酯的合成及生物活性", 《应用化学》, vol. 19, no. 02, 25 February 2002 (2002-02-25), pages 176 - 178 * |
| 马军安等: "取代苯甲醛肟羧酸酯的合成及生物活性研究(IV)――拟除虫菊酸4-二甲(乙)氨基苯甲醛肟酯的合成及生物活性", 《农药学学报》, vol. 01, no. 03, 15 August 1999 (1999-08-15), pages 8 - 13 * |
| 黄润秋等: "取代苯甲醛肟羧酸酯的合成及生物活性研究──Ⅰ.取代苯甲醛肟二氯菊酸酯的合成及生物活性", 《应用化学》, vol. 15, no. 01, 20 February 1998 (1998-02-20), pages 9 - 12 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106146350A (en) * | 2016-07-21 | 2016-11-23 | 华南理工大学 | A kind of new method of synthesizing amino methylcarbamoyl oximino ester derivant |
| CN106146350B (en) * | 2016-07-21 | 2017-10-20 | 华南理工大学 | A kind of new method of synthesizing amino formic acid oxime ester derivative |
| CN107954898A (en) * | 2017-12-01 | 2018-04-24 | 西北农林科技大学 | Salicylaldoxime ester type compound and preparation method thereof, purposes |
| CN110551098A (en) * | 2019-06-17 | 2019-12-10 | 湖北固润科技股份有限公司 | oxime ester photoinitiator containing five-membered aromatic heterocyclic structure and preparation and application thereof |
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