CN103467464B - Mosquito killing activity of 2,5-dithienylthiazole derivatives - Google Patents
Mosquito killing activity of 2,5-dithienylthiazole derivatives Download PDFInfo
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- CN103467464B CN103467464B CN201310438436.4A CN201310438436A CN103467464B CN 103467464 B CN103467464 B CN 103467464B CN 201310438436 A CN201310438436 A CN 201310438436A CN 103467464 B CN103467464 B CN 103467464B
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- 0 **(C=CC(C(Cl)=O)=C)=C Chemical compound **(C=CC(C(Cl)=O)=C)=C 0.000 description 2
- DUGFVJMUCIJZEX-UHFFFAOYSA-N CC(C)(C#Cc1ccc(-c2cnc(-c3ccc[s]3)[s]2)[s]1)N Chemical compound CC(C)(C#Cc1ccc(-c2cnc(-c3ccc[s]3)[s]2)[s]1)N DUGFVJMUCIJZEX-UHFFFAOYSA-N 0.000 description 1
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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 mosquito activity.
(2) background technology
Environment friendly agricultural is the direction of pesticide in future development, and photosensitive class agricultural chemicals because of its there is safety, low toxicity, fast, the many target of drug effect, the not easily advantage such as to develop immunity to drugs meet the developing direction of following environment friendly agricultural.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 while the effect playing weeding, desinsection, and self is also constantly being decomposed, and can not regenerate accumulation in object, 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 agricultural chemicals innovation always.
Terthienyl compounds, because of the biological activity of its uniqueness, is present in widely and has in bioactive natural product molecule.In recent years, the weeding of terthienyl, desinsection, antiviral activity receive extensive research respectively.Such as, under the condition of near-ultraviolet light photograph, terthienyl is to the LC of anopheles maculipalpis instar larvae
50for 11mg/L and dark time be then 154mg/L, its photoactivation cytotoxicity improves 14 times; Also have under illumination condition Aedes aegypti, Aedes albopictus and Culex quinquefasciatus and well kill activity.Because terthienyl structure is the structural pharmacophore of this compounds, by being modified with the new class medicament that may find that selectivity is good, activity is high, consumption is few, toxicity is low to terthienyl structure.
Due to 2,5-dithienyl thiazole derivative has good light enhanced activity, mainly concentrate on the research of such compound optoelectronic properties up till now, but without any in notebook patent particularly mentioned 2,5-dithienyl thiazole derivative, more kills mosquito activity without any what record these compounds particularly.
(3) summary of the invention
The object 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 compounds all show and kill mosquito activity.
(4) embodiment
Substantive distinguishing features of the present invention can be embodied from following embodiment, but it should not be considered as being 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-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-base) benzamide
Get in 3mmol2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-amine, 3.3mmol2-chloro-benzoyl chloride input 50mL two-mouth bottle, add 25mLTHF, 6mmol triethylamine is added again, reaction 5h after stirring and dissolving.Sterling is obtained through column chromatography.
The chloro-N-of embodiment 2:4-(2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-base) benzamide
Get in 3mmol2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-amine, 3.6mmol4-chloro-benzoyl chloride input 50mL two-mouth bottle, add 15mLTHF, 5.5mmol triethylamine is added again, reaction 5h after stirring and dissolving.Sterling is obtained through column chromatography.
The chloro-N-of embodiment 3:2,4-bis-(2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-base) benzamide
Get 3mmol2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-amine, 3.3mmol2,4-dichlorobenzoyl chloride drops in 50mL two-mouth bottle, add 25mL THF, 6mmol triethylamine is added again, reaction 5h after stirring and dissolving.Sterling is obtained through column chromatography.
The chloro-N-of embodiment 4:3,4-bis-(2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-base) benzamide
Get 3mmol2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-amine, 3.3mmol3,4-dichlorobenzoyl chloride drops in 50mL two-mouth bottle, add 25mL THF, 6mmol triethylamine is added again, reaction 5h after stirring and dissolving.Sterling is obtained through column chromatography.
The chloro-N-of embodiment 5:3,5-bis-(2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-base) benzamide
Get 3mmol2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-amine, 3.3mmol3,5-dichlorobenzoyl chloride drops in 50mL two-mouth bottle, add 25mL THF, 3mmol triethylamine is added again, reaction 5h after stirring and dissolving.Sterling is obtained through column chromatography.
Embodiment 6:3,5-dimethyl-N-(2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-base) benzamide
Get 3mmol2-methyl-4-(5-(2-(thiophene-2-base) thiazole-5-base) thiophene-2-base) fourth-3-alkynes-2-amine, 3.3mmol3,5-dimethyl benzoyl chloride drops in 50mL two-mouth bottle, add 25mL THF, 5mmol triethylamine is added again, reaction 5h after stirring and dissolving.Sterling is obtained 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 compound kills the mensuration of mosquito activity
Determine its kill ratio to culex pipiens pallens (Culex pipiens pallens) to determine the insecticidal activity of this series compound to target compound, its result is as shown in table 2.
Table 2 compound (I) kill mosquito determination of activity
This tests the normal population that culex pipiens pallens used is indoor feeding.Take target compound compound and be about 2mg in penicillin medicine bottle, add 10mL acetone (or suitable solvent), vibration is dissolved, and is 200ppm mother liquor.Pipette 1mL mother liquor, add and fill in the 100mL beaker of 89 ml waters, choose larvae at the beginning of 10 4 ages, pour in the lump in beaker together with 10mL feeding liquid, the concentration of its liquid is 2ppm.Process is put into standard treatment chamber, observe the growing state of mosquito larvae, have the timely sucking-off pupated, until all pupate or death.With the aqueous solution containing 1mL test solvent for blank.Mortality ratio graded index: +++ ++: >=80%; ++++: 60 ~ 79%; +++: 40 ~ 59%; ++: 20 ~ 39%:+ :≤19%.
Claims (2)
1. a 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. the application of 2,5-dithienyl thiazole compounds described in claim 1, is characterized in that killing mosquito activity.
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| 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 |
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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| 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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