CN103467464A - Mosquito killing activity of 2,5-dithienylthiazole derivatives - Google Patents
Mosquito killing activity of 2,5-dithienylthiazole derivatives Download PDFInfo
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- CN103467464A CN103467464A CN2013104384364A CN201310438436A CN103467464A CN 103467464 A CN103467464 A CN 103467464A CN 2013104384364 A CN2013104384364 A CN 2013104384364A CN 201310438436 A CN201310438436 A CN 201310438436A CN 103467464 A CN103467464 A CN 103467464A
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Abstract
The invention relates to the mosquito killing activity of 2,5-dithienylthiazole derivatives, wherein R represents 2-chloro, 4-chloro, 2,4-dichloro, 3,4-dichloro, 3,5-dichloro or 3,5-dimethyl. A compound (I) has 50% killing activity to 4-year early mosquito larvae under the circumstance of the formulation rate of 0.5 ppm.
Description
(1) technical field
What the present invention relates to 2,5-dithienyl thiazole derivative kills the mosquito activity.
(2) background technology
Environment friendly agricultural is the direction of pesticide in future development, and photosensitive class agricultural chemicals is because of it has safety, low toxicity, fast, the many target of drug effect, the advantage such as be difficult for developing immunity to drugs meets following environment friendly agricultural developing direction.Photosensitive class agricultural chemicals can utilize the light of occurring in nature and oxygen to produce the effects such as desinsection, sterilization, weeding.Because it is degraded rapidly at occurring in nature, photosensitive toxin is in the effect of performance weeding, desinsection, and self is also constantly being decomposed, and piles up in the object of can not regenerating, and can not transmit enrichment by food chain and cause secondary pollution.Therefore, the photosensitive class agricultural chemicals of Development of Novel is the important directions that people carry out the agricultural chemicals innovation always.
The terthienyl compounds, because of its unique biological activity, is present in widely and has in bioactive natural product molecule.In recent years, the weeding of terthienyl, desinsection, antiviral activity were received respectively broad research.For example, under the condition of near-ultraviolet light photograph, the LC of terthienyl to the anopheles maculipalpis instar larvae
50during for the 11mg/L dark, be 154mg/L, its photoactivation cytotoxicity has improved 14 times; Aedes aegypti, Aedes albopictus and Culex quinquefasciatus are also had and well kill activity under illumination condition.Due to the terthienyl structure pharmacophore structure that is this compounds, by being modified with of terthienyl structure, finding the new class medicament that selectivity is good, activity is high, consumption is few, toxicity is low.
Due to 2,5-dithienyl thiazole derivative has good light enhanced activity, mainly concentrate on up till now the research of such compound optoelectronic properties, but without any in notebook patent particularly mentioned 2,5-dithienyl thiazole derivative, more kill the mosquito activity without any what put down in writing particularly these compounds.
(3) summary of the invention
The purpose of this invention is to provide a kind of 2,5-dithienyl thiazole compound and its preparation method and application.
The present invention is following general formula (I) compound:
Wherein, R=2-chlorine, 4-chlorine, 2,4-dichloro, 3,4-dichloro, 3,5-dichloro, 3,5-dimethyl.
In the present invention 2,5-dithienyl thiazole compound has all shown and has killed the mosquito activity.
(4) embodiment
Substantive distinguishing features of the present invention can be embodied from following embodiment, but it should not to be considered as be any limitation of the invention.The compounds of this invention (I) synthetic route is:
The chloro-N-of embodiment 1:2-(2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-yl) benzamide
Get in 3mmol2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-amine, 3.3mmol2-chloro-benzoyl chloride input 50mL two-mouth bottle, add 25mLTHF, add again the 6mmol triethylamine after stirring and dissolving, reaction 5h.Obtain sterling through column chromatography.
The chloro-N-of embodiment 2:4-(2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-yl) benzamide
Get in 3mmol2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-amine, 3.6mmol4-chloro-benzoyl chloride input 50mL two-mouth bottle, add 15mLTHF, add again the 5.5mmol triethylamine after stirring and dissolving, reaction 5h.Obtain sterling through column chromatography.
Embodiment 3:2, the chloro-N-of 4-bis-(2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-yl) benzamide
Get 3mmol2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-amine, 3.3mmol2, the 4-dichlorobenzoyl chloride drops in the 50mL two-mouth bottle, add 25mL THF, add again the 6mmol triethylamine after stirring and dissolving, reaction 5h.Obtain sterling through column chromatography.
Embodiment 4:3, the chloro-N-of 4-bis-(2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-yl) benzamide
Get 3mmol2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-amine, 3.3mmol3, the 4-dichlorobenzoyl chloride drops in the 50mL two-mouth bottle, add 25mL THF, add again the 6mmol triethylamine after stirring and dissolving, reaction 5h.Obtain sterling through column chromatography.
Embodiment 5:3, the chloro-N-of 5-bis-(2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-yl) benzamide
Get 3mmol2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-amine, 3.3mmol3, the 5-dichlorobenzoyl chloride drops in the 50mL two-mouth bottle, add 25mL THF, add again the 3mmol triethylamine after stirring and dissolving, reaction 5h.Obtain sterling through column chromatography.
Embodiment 6:3,5-dimethyl-N-(2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-yl) benzamide
Get 3mmol2-methyl-4-(5-(2-(thiophene-2-yl) thiazole-5-yl) thiophene-2-yl) fourth-3-alkynes-2-amine, 3.3mmol3, the 5-dimethyl benzoyl chloride drops in the 50mL two-mouth bottle, add 25mL THF, add again the 5mmol triethylamine after stirring and dissolving, reaction 5h.Obtain sterling through column chromatography.
The physical parameter of compound the results are shown in Table 1.
The physical properties of table 1 compound (I) characterizes
Embodiment 7 target compounds kill the mensuration of mosquito activity
Target compound has been measured to the insecticidal activity that its kill ratio to culex pipiens pallens (Culex pipiens pallens) is determined this series compound, and its result is as shown in table 2.
Table 2 compound (I) kill the mosquito determination of activity
This tests the normal population that culex pipiens pallens used is indoor feeding.Take the about 2mg of target compound compound in the penicillin medicine bottle, add 10mL acetone (or suitable solvent), vibration is dissolved, and is the 200ppm mother liquor.Pipette the 1mL mother liquor, add in the 100mL beaker that fills 89 ml waters, choose larvae at the beginning of 10 4 ages, pour in the lump in beaker together with the 10mL feeding liquid, the concentration of its liquid is 2ppm.Processing is put into to the standard treatment chamber, observe the growing state of mosquito larvae, the timely sucking-off of pupating is arranged, until all pupate or death.The aqueous solution that contains the 1mL test solvent of take is blank.The mortality ratio graded index: ++ +++: >=80%; ++ ++: 60～79%; +++: 40～59%; ++: 20～39%:+ :≤19%.
Claims (2)
1. one kind 2,5-dithienyl thiazole compound is characterized in that it is the compound of general formula (I):
Wherein, R=2-chlorine, 4-chlorine, 2,4-dichloro, 3,4-dichloro, 3,5-dichloro, 3,5-dimethyl.
2. claim 1 is described 2, and the application of 5-dithienyl thiazole compound, is characterized in that killing the mosquito activity.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104045622A (en) * | 2014-07-04 | 2014-09-17 | 南开大学 | Tobacco mosaic virus resistant activity of N-(4-(2,2':5',2'-terthienyl-5-yl)-methylbutyl-3-alkynyl-2-yl) substituted benzamide compound |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1810801A (en) * | 2006-02-24 | 2006-08-02 | 华南农业大学 | Alkynyl thiofuran compound and its prepn and application |
| CN101402629A (en) * | 2008-11-19 | 2009-04-08 | 云南大学 | Synthesis and uses of terthienyl and derivatives thereof |
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2013
- 2013-09-22 CN CN201310438436.4A patent/CN103467464B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1810801A (en) * | 2006-02-24 | 2006-08-02 | 华南农业大学 | Alkynyl thiofuran compound and its prepn and application |
| CN101402629A (en) * | 2008-11-19 | 2009-04-08 | 云南大学 | Synthesis and uses of terthienyl and derivatives thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104045622A (en) * | 2014-07-04 | 2014-09-17 | 南开大学 | Tobacco mosaic virus resistant activity of N-(4-(2,2':5',2'-terthienyl-5-yl)-methylbutyl-3-alkynyl-2-yl) substituted benzamide compound |
| CN104045622B (en) * | 2014-07-04 | 2016-03-09 | 南开大学 | N-(4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) activity of resisting tobacco mosaic virus of substituted benzene formyl aminated compounds |
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