CN105348233A - 3-(2-furyl)propenol derivative as well as preparation method and application thereof - Google Patents
3-(2-furyl)propenol derivative as well as preparation method and application thereof Download PDFInfo
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- CN105348233A CN105348233A CN201510890291.0A CN201510890291A CN105348233A CN 105348233 A CN105348233 A CN 105348233A CN 201510890291 A CN201510890291 A CN 201510890291A CN 105348233 A CN105348233 A CN 105348233A
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- dehydrated alcohol
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- 0 *C(C=C1)=CC[C@@]1C(C=CC1=CC=CC1)=Cl Chemical compound *C(C=C1)=CC[C@@]1C(C=CC1=CC=CC1)=Cl 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen 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
- A01N43/08—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 oxygen as the ring hetero atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention provides a 3-(2-furyl)propenol derivative as well as a preparation method and application thereof. The derivative has a structural formula (I) shown in the following description; in the structural formula (I), R is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl, a methoxyl or a nitryl. The derivative provided by the invention is simple in structure, novel, easy to synthesize, and low in cost, and has a relatively good control effect on a plant pathogenic fungus.
Description
Technical field
The present invention relates to technical field of pesticide, particularly relate to a kind of 3-(2-furyl) allyl alcohol-like compound, preparation method and application thereof.
Background technology
Vinylcarbinol has another name called vinyl carbinol, is a kind of important fine chemicals.It is also the important intermediate of detergents and cosmetic, medicine and pesticide industry, for the production of epoxy chloropropane, glycerine, 1, the Chemicals such as 4-butyleneglycol, allylin, glycidyl allyl ether, Racemic glycidol, allylamine and allyl ester Type of Collective monomer, are also widely used in products such as manufacturing other medicine, agricultural chemicals and essence.
As everyone knows, furan nucleus is an electron rich system, easily forms intermolecular hydrogen bonding with multiple biological enzyme, therefore, some, containing the compound of furan nucleus, are natural or the biological activity all with wide spectrum of synthetic, such as, antibacterial, antiviral, antitumor, desinsection and weeding etc.Meanwhile, these compounds usually all have efficiently, low toxicity, to non-target organism safety, easily degrade in the environment, harmful organism is not easy to produce the feature such as resistance.At present, also furan nucleus is not introduced in vinylcarbinol molecular structure, synthesize the report that new compound is used as disinfectant use in agriculture use.
Summary of the invention
The object of the present invention is to provide a kind of new disinfectant use in agriculture namely active better, stability is better, and antimicrobial spectrum is wider, and toxicity is lower, and harmful organism is not easy to produce 3-(2-furyl) allyl alcohol-like compound of resistance, preparation method and application thereof.
A kind of 3-(2-furyl) allyl alcohol-like compound, its general structure is as follows:
In general formula (I), R is fluorine atom, chlorine atom, bromine atoms, atomic iodine, methyl, methoxyl group, nitro.
A kind of preparation method of 3-(2-furyl) allyl alcohol-like compound, comprising: the synthesis of intermediate and utilize described intermediate to carry out synthesising target compound two steps.
Further, method as above, the synthesis of described intermediate comprises the following steps:
A, in the mixture of 4-substituted acetophenone and dehydrated alcohol, add NaOH solution, form solution I;
B, under ice bath stirs, the mixed solution of furfural and dehydrated alcohol is slowly instilled in described solution I and reacts, formation solution II;
C, should complete after, add distilled water to solution II, regulate its pH value to neutral, have Precipitation, filter, washing, then use dehydrated alcohol recrystallization, namely obtain intermediate.
Further, method as above, described 4-substituted acetophenone is the one in 4-chloro-acetophenone, 4-bromoacetophenone, 4-fluoro acetophenone.
Further, method as above, the synthesis of target compound comprises the following steps:
E, in the mixed solution of described intermediate and dehydrated alcohol, add NaBH several times
4, after having reacted, underpressure distillation removing ethanol, until absence of liquid flows out;
F, to be cooled to room temperature, add sherwood oil wherein, be washed with distilled water to its pH value in neutral, to remove superfluous NaBH
4;
G, when the product obtained is liquid, with anhydrous sodium sulfate drying, filter, underpressure distillation removing sherwood oil, finally obtain the compounds of this invention; When the product obtained is solid, after underpressure distillation removing sherwood oil, then uses the mixed solvent recrystallization of dehydrated alcohol and sherwood oil, finally obtain the compounds of this invention.
Further, method as above, in described step g, the volume ratio of dehydrated alcohol and sherwood oil is 1:20.
Further, method as above, in described step b, temperature of reaction is 0-5 DEG C.
A kind of 3-(2-furyl) allyl alcohol-like compound is as mentioned above for preventing and treating the purposes of plant pathogenic fungi.
Further, purposes as above, described plant pathogenic fungi is Rhizoctonia solani Kuhn, fusarium graminearum, southern corn leaf blight, Sclerotinia sclerotiorum, botrytis cinerea, fruit white rot of grape bacterium, melon anthrax bacteria, Botryosphaeria berengeriana f. sp, citrus common green mold bacterium, phytophthora infestans.
Compound structure provided by the invention is simple, novel, and be easy to synthesis, cost is low, has good prevention effect to plant pathogenic fungi.Report is had no in plant pathogenic fungi inhibitor known at present.
Embodiment
For making the object, technical solutions and advantages of the present invention clearly, below technical scheme in the present invention be clearly and completely described, obviously, described embodiment is the present invention's part embodiment, instead of whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art, not making the every other embodiment obtained under creative work prerequisite, belong to the scope of protection of the invention.
The invention provides the compound that a class has bacteriostatic activity, its general structure is as follows:
In general formula (I), R is fluorine atom, chlorine atom, bromine atoms, atomic iodine, methyl, methoxyl group, nitro.
Principal reaction equation in the preparation of compounds that general formula is (I) is:
In formula, the implication of R is the same.
Embodiment 1:
Compound
(C
13h
11o
2f) preparation
(1) synthesis of intermediate 1-(4-fluorophenyl)-3-(2-furyl)-2-propylene-1-ketone
0.01mol4-fluoro acetophenone and 10mL dehydrated alcohol are added in 50mL three-necked bottle, then add 5mL10%NaOH solution wherein.Under ice bath stirs, the mixed solution constant pressure funnel of 0.01mol furfural and 10mL dehydrated alcohol is slowly instilled in three-necked bottle, react at 0-5 DEG C, and check whether reaction completes with thin-layer silicon offset plate (TLC).After having reacted, the distilled water of 3-4 times of volume is added in mixture, and regulate its pH value to neutral with the HCl of 10%, there is Precipitation, filter, washing, then use dehydrated alcohol recrystallization, namely obtain intermediate 1-(4-fluorophenyl)-3-(2-furyl)-2-propylene-1-ketone.
(2) synthesis of target compound
Homemade for 0.005mol intermediate and 30mL dehydrated alcohol are added in 50mL three-necked bottle, under stirring at room temperature, adds the NaBH of 0.015mol several times
4, and check whether reaction completes with TLC.After having reacted, underpressure distillation removing ethanol, until absence of liquid flows out.After allowing it be cooled to room temperature, add the sherwood oil of 2 times of volumes wherein and pour in separating funnel, being washed with distilled water to its pH value in neutral, to remove superfluous NaBH
4.And then be poured in Erlenmeyer flask, with anhydrous sodium sulfate drying, filter, underpressure distillation removing sherwood oil, obtain orange-yellow product liquid, yield is 82%.The spectral data of product is as follows:
1HNMR(300MHz,DMSO-d
6)δ(ppm):5.24(1H,t,J＝5.1Hz),5.69(1H,dd,J
1＝0.9Hz,J
2＝0.9Hz),6.17(1H,dd,J
1＝6.0Hz,J
2＝6.0Hz),6.41-6.51(3H,m),7.15(2H,t,J＝8.4Hz),7.38-7.42(2H,m),7.58(1H,s)；
13CNMR(75MHz,DMSO-d
6)δ(ppm):72.29(1C),108.56(1C),111.92(1C),115.09-115.37(d,2C),117.39(1C),124.59(1C),128.35-128.46(d,2C),140.77-140.81(d,1C),142.82(1C),152.36(1C),159.99-163.21(d,1C)。
Embodiment 2:
Compound
(C
13h
11o
2cl) preparation
(1) synthesis of intermediate 1-(4-chloro-phenyl-)-3-(2-furyl)-2-propylene-1-ketone
0.01mol4-chloro-acetophenone and 10mL dehydrated alcohol are added in 50mL three-necked bottle, then add 5mL10%NaOH solution wherein.Under ice bath stirs, the mixed solution constant pressure funnel of 0.01mol furfural and 10mL dehydrated alcohol is slowly instilled in three-necked bottle, react at 0-5 DEG C, and check whether reaction completes with thin-layer silicon offset plate (TLC).After having reacted, the distilled water of 3-4 times of volume is added in mixture, and regulate its pH value to neutral with the HCl of 10%, there is Precipitation, filter, washing, then use dehydrated alcohol recrystallization, namely obtain intermediate 1-(4-chloro-phenyl-)-3-(2-furyl)-2-propylene-1-ketone.
(2) synthesis of target compound
Homemade for 0.005mol intermediate and 30mL dehydrated alcohol are added in 50mL three-necked bottle, under stirring at room temperature, adds the NaBH of 0.015mol several times
4, and check whether reaction completes with TLC.After having reacted, underpressure distillation removing ethanol.Adding in the solid obtained after sherwood oil makes it dissolve completely pours in separating funnel, is washed with distilled water to its pH value in neutral, to remove superfluous NaBH
4.After underpressure distillation removing sherwood oil, then use the mixed solvent of dehydrated alcohol and sherwood oil (volume ratio is 1:20) recrystallization, obtain white powdery solids product, yield is 86%.The spectral data of product is as follows:
1HNMR(300MHz,DMSO-d
6)δ(ppm):5.24(1H,t,J＝5.7Hz),5.75(1H,d,J＝4.2Hz),6.14(1H,dd,J
1＝6.0Hz,J
2＝6.0Hz),6.42-6.51(3H,m),7.39(4H,s),7.58(1H,s)；
13CNMR(75MHz,DMSO-d
6)δ(ppm):72.21(1C),108.69(1C),111.96(1C),117.56(1C),128.34(2C),128.51(2C),131.78(1C),131.99(1C),142.92(1C),143.61(1C),152.28(1C)。
Embodiment 3:
Compound
(C
13h
11o
2br) preparation
(1) synthesis of intermediate 1-(4-bromophenyl)-3-(2-furyl)-2-propylene-1-ketone
0.01mol4-bromoacetophenone and 10mL dehydrated alcohol are added in 50mL three-necked bottle, then add 5mL10%NaOH solution wherein.Under ice bath stirs, the mixed solution constant pressure funnel of 0.01mol furfural and 10mL dehydrated alcohol is slowly instilled in three-necked bottle, react at 0-5 DEG C, and check whether reaction completes with thin-layer silicon offset plate (TLC).After having reacted, the distilled water of 3-4 times of volume is added in mixture, and regulate its pH value to neutral with the HCl of 10%, there is Precipitation, filter, washing, then use dehydrated alcohol recrystallization, namely obtain intermediate 1-(4-bromophenyl)-3-(2-furyl)-2-propylene-1-ketone.
(2) synthesis of target compound
Homemade for 0.005mol intermediate and 30mL dehydrated alcohol are added in 50mL three-necked bottle, under stirring at room temperature, adds the NaBH of 0.015mol several times
4, and check whether reaction completes with TLC.After having reacted, underpressure distillation removing ethanol, until absence of liquid flows out.After allowing it be cooled to room temperature, add the sherwood oil of 2 times of volumes wherein and pour in separating funnel, being washed with distilled water to its pH value in neutral, to remove superfluous NaBH
4.And then be poured in Erlenmeyer flask, with anhydrous sodium sulfate drying, filter, underpressure distillation removing sherwood oil, obtain safran product liquid, yield is 80%.The spectral data of product is as follows:
1HNMR(300MHz,DMSO-d
6)δ(ppm):5.23(1H,t,J＝5.1Hz),5.75(1H,d,J＝4.2Hz),6.16(1H,dd,J
1＝6.0Hz,J
2＝6.0Hz),6.41-6.52(3H,m),7.33(2H,d,J＝8.4Hz),7.52(2H,d,J＝8.1Hz),7.58(1H,s)；
13CNMR(75MHz,DMSO-d
6)δ(ppm):72.33(1C),108.66(1C),111.93(1C),117.65(1C),120.34(1C),128.72(2C),131.43(2C),131.94(1C),142.85(1C),144.02(1C),152.32(1C)。
Experimental example:
3-(2-furyl) allyl alcohol-like compound is to the Antibacterial Activity of plant pathogenic fungi
1, test plant pathogenic fungi
Rhizoctonia solani Kuhn, fusarium graminearum, southern corn leaf blight, Sclerotinia sclerotiorum, botrytis cinerea, fruit white rot of grape bacterium, melon anthrax bacteria, Botryosphaeria berengeriana f. sp, citrus common green mold bacterium and phytophthora infestans.
2, experimental technique
Test compound is dissolved in methyl-sulphoxide, then joins in the tap water containing 0.1% tween-80, after mixing, be made into the test solution of 150mg/L.This solution is joined in sterilized PDA substratum, add the Streptomycin sulphate that concentration is 50mg/L more simultaneously.Not contain the corresponding solution of test compound for blank, make thickness uniform pastille flat board for subsequent use, in triplicate.Choose Ф 5mm well-grown, pollution-free, the uniform bacterium cake of growing way with sterilized punch tool, aseptically access the center (each plating bacterium cake) of toxic substratum and control medium, cultivate under 28 DEG C of constant temperatures.When the colony diameter of blank grows to about 50mm, adopt right-angled intersection method to measure the diameter of bacterium colony, get its mean value, with the relative bacteriostasis rate of following formulae discovery:
3, experimental result
3-(2-furyl) allyl alcohol-like compound to the Antibacterial Activity result of plant pathogenic fungi as shown in table 1, table 2 and table 3.
Table 1 embodiment 1 compound when 150mg/L to the inhibit activities of plant pathogenic fungi
| Bacterial classification | Inhibiting rate (%) | Bacterial classification | Inhibiting rate (%) |
| Rhizoctonia solani Kuhn | 84.8 | Fruit white rot of grape bacterium | 95.7 |
| Fusarium graminearum | 81.1 | Melon anthrax bacteria | 90.6 |
| Southern corn leaf blight | 73.9 | Botryosphaeria berengeriana f. sp | 96.3 |
| Sclerotinia sclerotiorum | 98.4 | Citrus common green mold bacterium | 76.0 |
| Botrytis cinerea | 97.2 | Phytophthora infestans | 63.5 |
As known from Table 1, embodiment 1 compound has good inhibition to Sclerotinia sclerotiorum, botrytis cinerea, fruit white rot of grape bacterium, melon anthrax bacteria and Botryosphaeria berengeriana f. sp; Good inhibition is had to Rhizoctonia solani Kuhn and fusarium graminearum.
Table 2 embodiment 2 compound when 150mg/L to the inhibit activities of plant pathogenic fungi
| Bacterial classification | Inhibiting rate (%) | Bacterial classification | Inhibiting rate (%) |
| Rhizoctonia solani Kuhn | 94.2 | Fruit white rot of grape bacterium | 85.7 |
| Fusarium graminearum | 91.3 | Melon anthrax bacteria | 76.5 |
| Southern corn leaf blight | 82.9 | Botryosphaeria berengeriana f. sp | 83.2 |
| Sclerotinia sclerotiorum | 100.0 | Citrus common green mold bacterium | 97.1 |
| Botrytis cinerea | 100.0 | Phytophthora infestans | 66.4 |
As known from Table 2, embodiment 2 compound has good inhibition to Rhizoctonia solani Kuhn, fusarium graminearum, Sclerotinia sclerotiorum, botrytis cinerea and citrus common green mold bacterium; Good inhibition is had to southern corn leaf blight, fruit white rot of grape bacterium and Botryosphaeria berengeriana f. sp.
Table 3 embodiment 3 compound when 150mg/L to the inhibit activities of plant pathogenic fungi
| Bacterial classification | Inhibiting rate (%) | Bacterial classification | Inhibiting rate (%) |
| Rhizoctonia solani Kuhn | 96.8 | Fruit white rot of grape bacterium | 75.2 |
| Fusarium graminearum | 93.4 | Melon anthrax bacteria | 86.7 |
| Southern corn leaf blight | 100.0 | Botryosphaeria berengeriana f. sp | 65.9 |
| Sclerotinia sclerotiorum | 100.0 | Citrus common green mold bacterium | 77.6 |
| Botrytis cinerea | 100.0 | Phytophthora infestans | 83.5 |
As known from Table 3, embodiment 3 compound has good inhibition to Rhizoctonia solani Kuhn, fusarium graminearum, southern corn leaf blight, Sclerotinia sclerotiorum and botrytis cinerea; Good inhibition is had to melon anthrax bacteria and phytophthora infestans.
Last it is noted that above embodiment is only in order to illustrate technical scheme of the present invention, be not intended to limit; Although with reference to previous embodiment to invention has been detailed description, those of ordinary skill in the art is to be understood that: it still can be modified to the technical scheme described in foregoing embodiments, or carries out equivalent replacement to wherein portion of techniques feature; And these amendments or replacement, do not make the essence of appropriate technical solution depart from the spirit and scope of various embodiments of the present invention technical scheme.
Claims (9)
1. 3-(2-furyl) allyl alcohol-like compound, it is characterized in that, its general structure is as follows:
In general formula (I), R is fluorine atom, chlorine atom, bromine atoms, atomic iodine, methyl, methoxyl group or nitro.
2. a preparation method for 3-(2-furyl) allyl alcohol-like compound, is characterized in that, comprising: the synthesis of intermediate and utilize described intermediate to carry out synthesising target compound two steps.
3. method according to claim 2, is characterized in that, the synthesis of described intermediate comprises the following steps:
A, in the mixture of 4-substituted acetophenone and dehydrated alcohol, add NaOH solution, form solution I;
B, under ice bath stirs, the mixed solution of furfural and dehydrated alcohol is slowly instilled in described solution I and reacts, formation solution II;
C, should complete after, add distilled water to solution II, regulate its pH value to neutral, have Precipitation, filter, washing, then use dehydrated alcohol recrystallization, namely obtain intermediate.
4. the preparation method of agricultural chemical compound according to claim 3, it is characterized in that, described 4-substituted acetophenone is the one in 4-chloro-acetophenone, 4-bromoacetophenone, 4-fluoro acetophenone.
5. the preparation method of agricultural chemical compound according to claim 2, it is characterized in that, the synthesis of target compound comprises the following steps:
E, in the mixed solution of described intermediate and dehydrated alcohol, add NaBH several times
4, after having reacted, underpressure distillation removing ethanol, until absence of liquid flows out;
F, to be cooled to room temperature, add sherwood oil wherein, be washed with distilled water to its pH value in neutral, to remove superfluous NaBH
4;
G, when the product obtained is liquid, with anhydrous sodium sulfate drying, filter, underpressure distillation removing sherwood oil, finally obtain the compounds of this invention; When the product obtained is solid, after underpressure distillation removing sherwood oil, then uses the mixed solvent recrystallization of dehydrated alcohol and sherwood oil, finally obtain the compounds of this invention.
6. the preparation method of agricultural chemical compound according to claim 5, it is characterized in that, in described step g, the volume ratio of dehydrated alcohol and sherwood oil is 1:20.
7. method according to claim 3, is characterized in that, in described step b, temperature of reaction is 0-5 DEG C.
8. 3-(2-furyl) allyl alcohol-like compound described in a claim 1 is for preventing and treating the purposes of plant pathogenic fungi.
9. purposes according to claim 8, described plant pathogenic fungi is Rhizoctonia solani Kuhn, fusarium graminearum, southern corn leaf blight, Sclerotinia sclerotiorum, botrytis cinerea, fruit white rot of grape bacterium, melon anthrax bacteria, Botryosphaeria berengeriana f. sp, citrus common green mold bacterium, phytophthora infestans.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106432391A (en) * | 2016-09-09 | 2017-02-22 | 中国科学院西北高原生物研究所 | Novel steroid compound as well as preparation method and application thereof, and drug compound and application thereof |
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| CN101228872A (en) * | 2008-02-28 | 2008-07-30 | 四川大学 | Uses of chalcone synthesis on agricultural chemical |
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2015
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101228872A (en) * | 2008-02-28 | 2008-07-30 | 四川大学 | Uses of chalcone synthesis on agricultural chemical |
Non-Patent Citations (2)
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| HONG ZHANG ET AL.: "Design, Synthesis, and Bioactivities Screening of a Diaryl Ketone-Inspired Pesticide Molecular Library as Derived from Natural Products", 《CHEM BIOL DRUG DES》 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106432391A (en) * | 2016-09-09 | 2017-02-22 | 中国科学院西北高原生物研究所 | Novel steroid compound as well as preparation method and application thereof, and drug compound and application thereof |
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Application publication date: 20160224 |