CN104045622B - 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 - Google Patents

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 Download PDF

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Publication number
CN104045622B
CN104045622B CN201410314656.0A CN201410314656A CN104045622B CN 104045622 B CN104045622 B CN 104045622B CN 201410314656 A CN201410314656 A CN 201410314656A CN 104045622 B CN104045622 B CN 104045622B
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base
terthienyl
methyl
alkynes
activity
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CN104045622A (en
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朱有全
张海利
王丹阳
李蕾
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Nankai University
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Nankai University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The present invention relates to N-(4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) activity of the resisting tobacco mosaic virus of substituted benzene formyl aminated compounds.Wherein R=2-Cl; 2-CH 3; H; 2-CH 3o; 2-F; 2,4-dimethyl; 4-Cl; 3,5-dichloro; 2,6-difluoro; 2,6-dichloro; 2,5-difluoro; 2,4-dimethoxy; 2,6-dimethoxy; 2,4-dichloro; 3,4-dichloro; 3,5-dimethyl.In 500ppm formulation rate situation, inactivate activity, therapeutic activity and prolection are presented to tobacco mosaic virus (TMV).

Description

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
(1) technical field
The present invention relates to N-(4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) activity of the resisting tobacco mosaic virus of substituted benzene formyl aminated compounds.
(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, anti-tumor activity are subject to extensive research.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.
Because terthienyl derivative has good light enhanced activity, mainly concentrate on the research of such compound optoelectronic properties up till now, but without any N-(4-(2 mentioned in notebook patent particularly, 2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) substituted benzamide, more without any the activity of resisting tobacco mosaic virus recording these compounds particularly.
(3) summary of the invention
The object of this invention is to provide a kind of N-(4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) substituted benzene formyl aminated compounds and its preparation method and application.
The present invention is following general formula (I) compound:
Wherein R=2-Cl; 2-CH 3; H; 2-CH 3o; 2-F; 2,4-dimethyl; 4-Cl; 3,5-dichloro; 2,6-difluoro; 2,6-dichloro; 2,5-difluoro; 2,4-dimethoxy; 2,6-dimethoxy; 2,4-dichloro; 3,4-dichloro; 3,5-dimethyl.In 500ppm formulation rate situation, inactivate activity, therapeutic activity and prolection are all presented to tobacco mosaic virus (TMV).
(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:
Embodiment 1:N-(4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) adjacent chlorobenzamide (1a)
0.011 mole of 2-chloro-benzoyl chloride is added in 50 milliliters of reaction flasks, 20 milliliters of N through Non-aqueous processing, N-N,N-DIMETHYLACETAMIDE, stir, add 0.011 mole of 4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-amine; stirring at room temperature to raw material point (amine) disappears substantially, new point no longer changes, about 24 hours.Concentrated, obtain sterling through column chromatography process.
Embodiment 2:N-(4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) o-methyl-benzene methane amide (1b)
0.011 mole of o-methyl-benzene formyl chloride is added in 50 milliliters of reaction flasks, 20 milliliters of N through Non-aqueous processing, N-N,N-DIMETHYLACETAMIDE, stir, add 0.011 mole of 4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-amine; stirring at room temperature to raw material point (amine) disappears substantially, new point no longer changes, about 24 hours.Concentrated, obtain sterling through column chromatography process.
Embodiment 3:N-(4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) benzamide (1c)
0.011 mole of Benzoyl chloride is added in 50 milliliters of reaction flasks, 20 milliliters of N through Non-aqueous processing, N-N,N-DIMETHYLACETAMIDE, stir, add 0.011 mole of 4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-amine; stirring at room temperature to raw material point (amine) disappears substantially, new point no longer changes, about 24 hours.Concentrated, obtain sterling through column chromatography process.
Synthesized compound (1) according to similar method, the physical parameter result of compound and to tobacco mosaic virus (TMV) inhibiting rate in table 1.
Embodiment 4 pairs of tobacco mosaic virus (TMV) inhibiting rate tests
Live body provide protection: choose 3 ~ 5 leaf phase Nicotiana glutinosas that growing way is consistent, be limited with main lobe arteries and veins, with writing brush by medicament dab in Zuo Banye, right half leaf be coated with clear water contrast, often process 5 times repeat.Process is placed on observation ward, dries rear full leaf frictional inoculation tobacco mosaic virus (TMV).After 2 ~ 3d, record left and right half leaf withered spot number, calculates preventive effect respectively.
Live body therapeutic action:: choose 3 ~ 5 leaf phase Nicotiana glutinosas that growing way is consistent, full leaf frictional inoculation TMV, after drying, Zuo Banye spreads medicament, and right half leaf is coated with clear water contrast, often processes 5 times and repeats.After 2 ~ 3d, record left and right half leaf withered spot number, calculates preventive effect respectively.
Live body passivation: the TMV virus after Passivation Treatment and medicament mixed solution are applied in left half leaf of Nicotiana glutinosa, and right half leaf establishes homogenous quantities concentration Virus eliminating medicine water mixed liquid to contrast, and often processes 5 times and repeats.After 2 ~ 3d, record left and right half leaf withered spot number, calculates preventive effect respectively.
The physical properties of table 1 compound (1) characterizes tobacco mosaic virus (TMV) inhibiting rate (%; Concentration: 500ppm)

Claims (2)

1. a N-(4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) substituted benzene formyl aminated compounds, it is characterized in that it is the compound of general formula (I):
Wherein R=2-chlorine; 2-methyl; Hydrogen; 2-methoxyl group; 2-fluorine; 2,4-dimethyl; 4-chlorine; 3,5-dichloro; 2,6-difluoro; 2,6-dichloro; 2,5-difluoro; 2,4-dimethoxy; 2,6-dimethoxy; 2,4-dichloro; 3,4-dichloro; 3,5-dimethyl.
2. N-described in claim 1 (4-(2,2 ': 5 ', 2 "-terthienyl-5-base)-2-methyl fourth-3-alkynes-2-base) application of substituted benzene formyl aminated compounds, it is characterized in that the restraining effect to tobacco mosaic virus (TMV).
CN201410314656.0A 2014-07-04 2014-07-04 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 Expired - Fee Related CN104045622B (en)

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CN108191844A (en) * 2018-01-16 2018-06-22 南开大学 The activity of the resisting tobacco mosaic virus of the 2- methyl butyne amine acylated derivatives of the dithienyl pyridine structure containing 2,6-

Citations (3)

* Cited by examiner, † Cited by third party
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
CN103467464A (en) * 2013-09-22 2013-12-25 南开大学 Mosquito killing activity of 2,5-dithienylthiazole derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
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
CN103467464A (en) * 2013-09-22 2013-12-25 南开大学 Mosquito killing activity of 2,5-dithienylthiazole derivatives

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