CN1704414A - 1-aryl pyrazole oxime derivatives and their preparing process and use - Google Patents
1-aryl pyrazole oxime derivatives and their preparing process and use Download PDFInfo
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- CN1704414A CN1704414A CN 200410022663 CN200410022663A CN1704414A CN 1704414 A CN1704414 A CN 1704414A CN 200410022663 CN200410022663 CN 200410022663 CN 200410022663 A CN200410022663 A CN 200410022663A CN 1704414 A CN1704414 A CN 1704414A
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Abstract
The invention relates to 1-aryl pyrazole oxime derivatives having a general formula (I) and their preparing process, wherein R1 is C1-C4 alkyl, one or more halogen atoms, R2 is halogen, or formula (II) wherein A is N, C, R3 is C1-C3 alkyl, alkoxy, halogen, or halogenated alkyl. The compounds provided by the invention can be used as pesticides, and 22 derivatives can be obtained through artificial synthesis.
Description
Technical field: the present invention is one group of new compound with used as pesticides: the preparation method of 1-arylpyrazole oxime derivatives and 1-arylpyrazole oxime derivatives.
Background technology: U.S. Pat 4843068 in 1989 has reported that the pyrazol oxime ether compound has the Insecticiding-miticiding effect.European patent EP 0390498 and Japanese Patent JP3240775 have reported that the pyrazol oxime ether compound has desinsection, kills mite and sterilization effect in succession, and introduced the synthetic of this series compound, the group of ether moiety mainly is compounds such as alkyl, thiazolinyl and substituted-phenyl.Invention of the present invention goes into to find that 2-chlorine 5-methylene radical-pyridyl is common active groups such as the efficient nicotinic insecticide Provado of a class, pyrrole worm are clear, acetamiprid, Ti304.
The objective of the invention is with the synthetic one group of new compound of artificial synthetic method.The pyrazol oxime ether group that had both contained Insecticiding-miticiding and sterilization effect in the compound, the while is also contained the group of the 2-chlorine 5-methylene radical-pyridyl of efficient nicotinic insecticide, and this compounds is the pyrazol oxime ether new compound that contains pyridine ring.
Summary of the invention: the present invention introduces pyridine ring in pyrazoles oxime ether, groups such as phenyl ring in the replacement pyrazoles oxime ether and alkyl.Synthesized the pyrazol oxime ether new compound that contains pyridine ring, i.e. 1-arylpyrazole oxime derivatives.They have the structural formula of general structure (I).
R
1Represent hydrogen; C
1-C
4Alkyl; One or more halogen atoms.
R
2=represent halogen or formula
Wherein A represents nitrogen, carbon; R
3Represent C
1-C
3Alkyl, alkoxyl group, one or more halogen atoms, the alkyl that one or more halogen atoms replace.
The compound of synthetic general formula (I) expression, the method for available following chemical formulation is synthetic:
R in the general formula (II)
1, R
2Identical with the front definition.
Acid binding agent can be organic bases or mineral alkali.
Can synthesize the represented compound of general formula (II) by following method:
The synthetic represented compound of general formula (III) can synthesize with the A and the B method of chemical formulation:
Method A:
Method B:
R in the formula
1, R
2, R
3Identical with the definition of front general formula (I), general formula (III) can be obtained through a step or two-step reaction by 5-pyrazolone and suitable reagent, makes resulting general formula (III) and azanol reaction make (II) then.
Particular compound architecture formula with the pyrazoles oxime ether of general formula (I) expression is as follows.
Embodiment 1: the preparation method of compound 12:
That is: the preparation method of 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-fluorobenzene sulfenyl)-4-pyrazoles-aldoxime-(2-chloro-5-picolyl) ether:
1.6 gram 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-fluorobenzene sulfenyl)-4-pyrazolyl aldoxime is joined in the 100ml there-necked flask, add 0.19 gram sodium hydroxide, adding DMF15ml stirred after 30 minutes, add 2-chloro-5-chloromethylpyridine 0.76 gram, stirring at normal temperature 2h, TCL follows the tracks of reaction to fully, pours in the 100ml water suction filtration, drying into.Sherwood oil and re-crystallizing in ethyl acetate get the cotton-shaped crystal of white cotton, 130 ℃ of fusing points, yield 88%.Structure is confirmed through H-NMR.
Embodiment 2: the preparation method of compound 5:
That is: the preparation method of 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-methylbenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether:
2.0 gram 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-methylbenzene sulfenyl)-4-pyrazolyl aldoxime is joined in the 100ml there-necked flask, add 0.24 gram sodium hydroxide, adding DMF15m1 stirred after 30 minutes, add 2-chloro-5-chloromethylpyridine 0.96 gram, stirring at normal temperature 2h, TCL follow the tracks of reaction to fully, pour in the 100ml water, suction filtration, drying.Sherwood oil and re-crystallizing in ethyl acetate get the cotton-shaped crystal of white cotton, 109 ℃ of fusing points, yield 92%.Structure is confirmed through H-NMR.
Embodiment 3: the preparation method of compound 6:
That is: the preparation method of 1-phenyl-3-methyl-5-(4 '-anisole sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether::
1.8 gram 1-phenyl-3-methyl-5-(4 '-p-methoxy-phenyl base)-4-pyrazolyl aldoxime is joined in the 100ml there-necked flask, add 0.22 gram potassium hydroxide, adding DMF15ml stirred after 30 minutes, add 2-chloro-5-chloromethylpyridine 0.86 gram, stirring at normal temperature 2h, TCL follow the tracks of reaction to fully, pour in the 100ml water, suction filtration, drying.Sherwood oil and re-crystallizing in ethyl acetate get the cotton-shaped crystal of white cotton, 99 ℃ of fusing points, yield 88%.Structure is confirmed through H-NMR.
Embodiment 4: the preparation method of compound 10:
That is: the preparation method of 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-methylbenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether::
1.6 gram 1-(4 '-chloro-phenyl-)-3-methyl-5-(4 '-methylbenzene sulfenyl)-4-pyrazolyl aldoxime is joined in the 100ml there-necked flask, add 0.18 gram sodium hydroxide, adding DMF15ml stirred after 30 minutes, add 2-chloro-5-chloromethylpyridine 0.73 gram, stirring at normal temperature 2h, TCL follow the tracks of reaction to fully, pour in the 100ml water, suction filtration, drying.Sherwood oil and re-crystallizing in ethyl acetate get white needle-like crystals, 104 ℃ of fusing points, yield 88%.Structure is confirmed through H-NMR.
The preparation method of other compound of the present invention is to be raw material with different separately pyrazoles aldoximes as: compound 1,2,3,4,7,8,9,11,13,14,15,16,17,18,19,20,21,22, in the DMF solvent, under alkaline condition, get with the reaction of 2-chloro-5-chloromethylpyridine.Raw material is pressed the formula weight proportioning.Reaction conditions is a stirring at normal temperature, the product filtration drying and through sherwood oil and re-crystallizing in ethyl acetate and pure product.Particular compound get title and used raw material as follows:
Compound 1:1-phenyl-3-methyl-5-chloro-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-phenyl-3-methyl-5-chloro-4-pyrazolyl aldoxime
Compound 2:1-(4 '-chloro-phenyl-)-3-methyl-5-fluoro-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether
Raw material: 1-(4 '-chloro-phenyl-)-3-methyl-5-fluoro-4-pyrazolyl aldoxime
Compound 4:1-phenyl-3-methyl-5-(4 '-the methylbenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether
Raw material: 1-phenyl-3-methyl-5-(4 '-the methylbenzene sulfenyl)-the 4-pyrazolyl aldoxime
Compound 7:1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the anisole sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the anisole sulfenyl)-the 4-pyrazolyl aldoxime
Compound 8:1-(4 '-chloro-phenyl-)-3-methyl-5-(4 '-the trifluoromethoxy thiophenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-(4 '-chloro-phenyl-)-3-methyl-5-(4 '-the trifluoromethoxy thiophenyl)-the 4-pyrazolyl aldoxime
Compound 9:1-(4 '-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-(4 '-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-the 4-pyrazolyl aldoxime
Compound 11:1-phenyl-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-phenyl-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-the 4-pyrazolyl aldoxime
Compound 13:1-(4 '-aminomethyl phenyl)-3-methyl-5-(2-pyridine sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-(4 '-aminomethyl phenyl)-3-methyl-5-(2-pyridine sulfenyl)-4-pyrazolyl aldoxime
Compound 15:1-phenyl-3-methyl-5-(4 '-the trifluoromethyl thiophenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-phenyl-3-methyl-5-(4 '-the trifluoromethyl thiophenyl)-the 4-pyrazolyl aldoxime
Compound 16:1-phenyl-3-methyl-5-(2-chlorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-phenyl-3-methyl-5-(2-chlorobenzene sulfenyl)-4-pyrazolyl aldoxime
Compound 17:1-(4 '-chloro-phenyl-)-3-methyl-5-chloro-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-(4 '-chloro-phenyl-)-3-methyl-5-chloro-4-pyrazolyl aldoxime
Compound 18:1-(3-chloro-phenyl-)-3-methyl-5-(2-pyridine sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-(3-chloro-phenyl-)-3-methyl-5-(2-pyridine sulfenyl)-4-pyrazolyl aldoxime
Compound 19:1-(3-chloro-phenyl-)-3-methyl-5-(4 '-the methylbenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-(3-chloro-phenyl-)-3-methyl-5-(4 '-the methylbenzene sulfenyl)-the 4-pyrazolyl aldoxime
Compound 21:1-(2-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-(2-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-the 4-pyrazolyl aldoxime
Compound 22:1-(3-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether.
Raw material: 1-(3-chloro-phenyl-) 3-methyl-5-(4 '-fluorobenzene sulfenyl)-4-pyrazolyl aldoxime 1-arylpyrazole of the present invention oxime derivatives is 22 kinds among the embodiment not only, as (I),
(III) in the general formula, R
1Represent C
1-C
4Alkyl, one or more halogen atom.R
2Represent halogen or formula
, wherein A represents nitrogen, carbon; R
3Represent C
1-C
3Alkyl, alkoxyl group; Halogen; Haloalkyl does not all exemplify one by one.In these compounds,, therefore have desinsection simultaneously, kill mite and sterilization effects because general formula contains pyrazoles oxime ether group and 2-chloro-5-methylene radical-pyridine group.This effect may be better than independent pyrazol oxime ether compound or the independent compound effect that contains 2-chloro-5-methylene radical-pyridyl.On agricultural, broad application prospect should be arranged with used as pesticides.
The fusing point data of part of compounds and results of elemental analyses and hydrogen nuclear magnetic resonance data:
| Compound number | Fusing point ℃ | Ultimate analysis: actual value (theoretical value) | ||
| ?C | H | N | ||
| Compound 4 | ?96 | ?63.72(64.20) | 4.38(4.71) | 12.60(12.84) |
| Compound 5 | ?108 | ?64.70(64.85) | 4.85(5.01) | 11.89(12.10) |
| Compound 6 | ?99 | ?61.89(62.00) | 4.20(4.55) | 11.60(12.05) |
| Compound 9 | ?137 | ?56.50(56.68) | 3.60(3.52) | 11.30(11.50) |
| Compound 10 | ?104 | ?59.25(59.63) | 4.02(4.17) | 11.48(11.59) |
| Compound 11 | ?100 | ?60.55(60.99) | 3.79(4.01) | 12.10(12.37) |
| Compound 12 | ?130 | ?61.55(61.73) | 4.21(4.32) | 11.85(12.00) |
Part of compounds
1HNMR (CDCl
3, 400MHz) data:
Compound 3:2.41 (s, 6H, 5.14 (s, 2H), 7.26～7.28 (d, 2H), 7.32～7.39 (t, 3H), 7.71～7.39 (d, 2H), 8.09 (s, 1H), 8.45 (s, 1H)
Compound 4:2.26 (s, 3H), 2.49 (s, 3H), 5.12 (s, 2H), 6.81～6.83 (d, 2H), 6.97～6.99 (d, 2H), 7.26～7.38 (m, 6H), 7.68～7.70 (d, 1H), 8.25 (s, 1H), 8.43 (s, 1H)
Compound 5:
2.26(s，3H)，2.36(s，3H)，2.48(s，3H)，5.11(s，2H)，6.82～6.84(d，2H)，6.98～7.00(d，1H)，7.15～7.13(d，2H)，7.24～7.26(d，2H)，7.30～7.32(d，1H)，7.67～7.69(d，2H)，8.23(s，1H)，8.42(s，1H)
Compound 6:
2.46(s，3H)，3.73(s，3H)，5.13(s，2H)，6.67～6.70(d，2H)，6.86-6.89(d，2H)，7.26～7.37(m，6H)，7.6～7.72(m，1H)，8.31(s,1H)，8.43(s，1H)
Compound 9:
2.47(s，3H)，5.14(s，2H)，6.89～6.90(d，4H)，7.26～7.36(m，5H)，7.69～7.71(d，2H)，8.25(s，1H)，8.43(s，1H)
Compound 10:
2.26(s，3H)，2.48(s，3H)，5.13(S，2H)，6.81-6.83(d，2H)，6.99-7.01(d，2H)，7.26-7.37(m，5H)，7.68-7.02(d，2H)，8.25(s，1H)，8.43(s，1H)
Compound 11:
2.48(s，3H)，5.13(s，2H)，6.84～6.88(d，4H)，6.89～7.36(m，6H)，7.69～7.71(d，1H)，8.26(s，1H)，8.44(s，1H)
Compound 12:
2.37(s，3H)，2.47s，3H)，5.13(s，2H)，6.85～6.90(m，4H)，7.16～7.26(d，4H)，7.342～7.34(d，2H)，7.69～7.71(d，1H)，8.24(s，1H)，8.43(s，1H)
From top digital proof the structure of compound that embodiment lifts.
Claims (4)
1, a class is used for agricultural insecticide, kills mite and germ-resistant compound, it is characterized in that a compounds of synthetic, 1-arylpyrazole oxime derivatives, and its compound structure general formula is as follows:
In the formula: R
1Represent C
1-C
4Alkyl, one or more halogen atom.R
2Represent halogen, or formula
Wherein A represents nitrogen, carbon; R
3Represent C
1-C
3Alkyl, alkoxyl group; One or more halogen atoms; The alkyl that one or more halogen atoms replace.
2. a class according to claim 1 is used for agricultural insecticide, kills mite and germ-resistant compound, it is characterized in that synthetic compound has the derivative of following 22 kinds of 1-arylpyrazole oxime ethers, and its structural formula is as follows:
3, a class according to claim 1 and 2 is used for agricultural insecticide, kills the preparation method of mite and germ-resistant compound, it is characterized in that with different separately pyrazoles aldoximes be raw material, in the DMF solvent, under alkaline condition, get with the reaction of 2-chloro-5-chloromethylpyridine, raw material is pressed the formula weight proportioning, reaction conditions is a stirring at normal temperature, the product filtration drying and through sherwood oil and re-crystallizing in ethyl acetate and pure product.
4, a class according to claim 3 is used for agricultural insecticide, kills the preparation method of mite and germ-resistant compound, it is characterized in that the title and the corresponding pyrazoles aldoxime raw material of 22 kinds of compounds of synthetic are as follows:
Compound 1; 1-phenyl-3-methyl-5-chloro-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-phenyl-3-methyl-5-chloro-4-pyrazolyl aldoxime;
Compound 2:1-(4 '-chloro-phenyl-)-3-methyl-5-fluoro-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether
Raw material: 1-(4 '-chloro-phenyl-)-3-methyl-5-fluoro-4-pyrazolyl aldoxime;
Compound 3:1-(4 '-aminomethyl phenyl)-3-methyl-5-chloro-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(4 '-aminomethyl phenyl)-3-methyl-5-chloro-4-pyrazolyl aldoxime;
Compound 4:1-phenyl-3-methyl-5-(4 '-the methylbenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-phenyl-3-methyl-5-(4 '-the methylbenzene sulfenyl)-the 4-pyrazolyl aldoxime;
Compound 5:1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the methylbenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the methylbenzene sulfenyl)-the 4-pyrazolyl aldoxime;
Compound 6:1-phenyl-3-methyl-5-(4 '-the anisole sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-phenyl-3-methyl-5-(4 '-the anisole sulfenyl)-the 4-pyrazolyl aldoxime;
Compound 7:1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the anisole sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the anisole sulfenyl)-the 4-pyrazolyl aldoxime;
Compound 8:1-(4 '-chloro-phenyl-)-3-methyl-5-(4 '-the trifluoromethoxy thiophenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(4 '-chloro-phenyl-)-3-methyl-5-(4 '-the trifluoromethoxy thiophenyl)-the 4-pyrazolyl aldoxime;
Compound 9:1-(4 '-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(4 '-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-the 4-pyrazolyl aldoxime;
Compound 10:1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the methylbenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the methylbenzene sulfenyl)-the 4-pyrazolyl aldoxime;
Compound 11:1-phenyl-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-phenyl-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-the 4-pyrazolyl aldoxime;
Compound 12:1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles-aldoxime-(2-chloro-5-picolyl) ether,
Raw material: 1-(4 '-aminomethyl phenyl)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles-formoxime;
Compound 13:1-(4 '-aminomethyl phenyl)-3-methyl-5-(2-pyridine sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(4 '-aminomethyl phenyl)-3-methyl-5-(2-pyridine sulfenyl)-4-pyrazolyl aldoxime;
Compound 15:1-phenyl-3-methyl-5-(4 '-the trifluoromethyl thiophenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-phenyl-3-methyl-5-(4 '-the trifluoromethyl thiophenyl)-the 4-pyrazolyl aldoxime;
Compound 16:1-phenyl-3-methyl-5-(2-chlorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-phenyl-3-methyl-5-(2-chlorobenzene sulfenyl)-4-pyrazolyl aldoxime;
Compound 17:1-(4 '-chloro-phenyl-)-3-methyl-5-chloro-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(4 '-chloro-phenyl-)-3-methyl-5-chloro-4-pyrazolyl aldoxime;
Compound 18:1-(3-chloro-phenyl-)-3-methyl-5-(2-pyridine sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(3-chloro-phenyl-)-3-methyl-5-(2-pyridine sulfenyl)-4-pyrazolyl aldoxime;
Compound 19:1-(3-chloro-phenyl-)-3-methyl-5-(4 '-the methylbenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(3-chloro-phenyl-)-3-methyl-5-(4 '-the methylbenzene sulfenyl)-the 4-pyrazolyl aldoxime;
Compound 21:1-(2-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(2-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-the 4-pyrazolyl aldoxime;
Compound 22:1-(3-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-4-pyrazoles aldoxime-(2-chloropyridine methyl) ether,
Raw material: 1-(3-chloro-phenyl-)-3-methyl-5-(4 '-the fluorobenzene sulfenyl)-the 4-pyrazolyl aldoxime;
Various pyrazoles aldoximes and 2-chloro-5-chloromethylpyridine are pressed the formula weight proportioning in the preparation process, in the DMF solvent, under alkaline condition as: sodium hydroxide or potassium hydroxide, reaction obtains.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675205A (en) * | 2012-05-25 | 2012-09-19 | 安徽农业大学 | Pyrazol oxime ether compound and preparation method and application thereof in anticancer therapy |
| CN103265479A (en) * | 2013-06-14 | 2013-08-28 | 南开大学 | Synthetic method of 6-chloromethyl niacin tert-butyl ester |
| CN110092776A (en) * | 2019-04-30 | 2019-08-06 | 南通大学 | The pyrazoles oxime ester compound and its preparation method and application of the connection polyfluoro pyrrazole structure containing pyridine |
-
2004
- 2004-05-28 CN CN 200410022663 patent/CN1704414A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675205A (en) * | 2012-05-25 | 2012-09-19 | 安徽农业大学 | Pyrazol oxime ether compound and preparation method and application thereof in anticancer therapy |
| CN102675205B (en) * | 2012-05-25 | 2014-08-20 | 安徽农业大学 | Pyrazol oxime ether compound and preparation method and application thereof in anticancer therapy |
| CN103265479A (en) * | 2013-06-14 | 2013-08-28 | 南开大学 | Synthetic method of 6-chloromethyl niacin tert-butyl ester |
| CN103265479B (en) * | 2013-06-14 | 2017-12-08 | 南开大学 | A kind of synthetic method of the 6 chloromethyl nicotinic acid tert-butyl ester |
| CN110092776A (en) * | 2019-04-30 | 2019-08-06 | 南通大学 | The pyrazoles oxime ester compound and its preparation method and application of the connection polyfluoro pyrrazole structure containing pyridine |
| CN110092776B (en) * | 2019-04-30 | 2021-09-07 | 南通大学 | Pyrazole oxime ester compound containing pyridine-difluoride pyrazole structure and preparation method and application thereof |
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