CN104222106A - Application of 2,5-substituent-1,3,4-oxadiazole sulfone derivatives with function of preventing and controlling bacterial diseases of crops - Google Patents
Application of 2,5-substituent-1,3,4-oxadiazole sulfone derivatives with function of preventing and controlling bacterial diseases of crops Download PDFInfo
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- CN104222106A CN104222106A CN201410420432.8A CN201410420432A CN104222106A CN 104222106 A CN104222106 A CN 104222106A CN 201410420432 A CN201410420432 A CN 201410420432A CN 104222106 A CN104222106 A CN 104222106A
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Abstract
The invention discloses application of 2,5-substituent-1,3,4-oxadiazole sulfone derivatives with a function of preventing and controlling bacterial diseases of crops. The invention relates to the technical field of chemical engineering and pesticides. A specific technology is as follows: compounds with the type are capable of effectively preventing and controlling citrus bacterial canker and Chinese cabbage soft rot, wherein EC50 values of a compound-2-(4-fluorobenzyl)-5-methylsufonyl-1,3,4-oxadiazole to pathogenic bacteria of the citrus bacterial canker and pathogenic bacteria of the Chinese cabbage soft rot are respectively 1.23 and 29.56 micrograms/ml, and the preventing and controlling effects are best. The 2,5-substituent-1,3,4-oxadiazole sulfone derivatives are applied to the prevention and control of the bacterial disease of the crops, are simple in structure, simple in preparation process, low in production cost, and wide in application prospect. The 2,5-substituent-1,3,4-oxadiazole sulfone derivatives have a following general formula described in the specification.
Description
Technical field
The present invention relates to chemical industry and technical field of pesticide, concrete technology is the application of 2,5-substituting group-1,3, the 4-oxadiazole sulfone derivatives with control crop bacterial disease.
Background technology
China, as large agricultural country, is ensureing that the status of agricultural production Pesticides is of crucial importance.In recent years, along with the continuous change of the trend such as the continuous differentiation of China's agricultural planting structure, climatic variation, foreign term and traditional pesticide resistance increase, in China's agricultural production, chief crop disease presents the features such as frequency is high, serious extent, occurrence scope wide, prevention and control difficulty is large; In addition disease drug resistance strengthens, conventional dose preventive effect is undesirable, agricultural product remain factors such as exceeding standard, causes huge economic loss to agricultural production.For current agricultural significant crop bacterial disease problem, find safety scientific and efficiently and have green candidate's agricultural chemicals of potential market vitality to be the vital task faced in China's New pesticides discovery basic research.Guide finds it is the key realizing innovation green chemical pesticide, and design optimization synthesizes some class agricultural chemicals guide structures, the green chemical pesticide of development of new low toxicity, low-residual, safety, seems very urgent and important.
The crop bacterial disease caused by pathogenetic bacteria is a class Major Diseases of crop, and wherein the crop bacterial disease such as citrus bacterial canker disease, soft rot of cabbage, bacterial blight of rice, paddy rice bacterium cecospora spot is all worldwide important disease.In recent years along with climatic variation, the joint effect of the factors such as the change of crop varieties and the fast development of industrialized agriculture, the loss that crop bacterial disease causes increases the weight of year by year, lack effective chemical control medicament simultaneously, cause crop pest to be just difficult to be effectively controlled at short notice once extensive generation.
1,3,4-oxadiazole heterocyclic compounds contains the five member ring heterocyclic compound of O, atom N, and its cyclic skeleton has obvious conjugation and aromaticity, thus has biologically active widely.1,3,4-oxadiazole derivative has antimycotic, antibacterium, weeding, desinsection, the biologically active such as antiviral in agricultural chemicals, offshore company in succession develops and multiplely contains 1,3, the agricultural chemicals of 4-oxadiazole structure, as having stomach toxicity, action of contace poison except the Evil humulone of the annual unifacial leaf in paddy field and broadleaf weed to insect, main as hygienic insecticide control housefly, cockroach.To pest specific Sha Chong Ji Evil worm ketone such as aphid, plant hopper, leafhopper also containing 1,3,4-oxadiazole structure.
Sulfone compound has broad-spectrum biological activity, has desinsection, antimycotic, antibacterium, weeding, the biologically active such as antiviral in agricultural chemicals.Sulfone compound receives more concern in agricultural bactericidal, since Uniroyal,Inc. of the U.S. in 1966 successfully promotes disinfectant use in agriculture oxycarboxin, people conduct in-depth research this compounds in recent decades, in succession develop the bactericide such as Euparen, tolyfluanid, cyazofamid, amisulbrom.Due to its excellent physiologically active, thus the focus that current environment friendly agricultural formulates is remained to its MOLECULE DESIGN, synthesis and bioactivity research.
Bright (Xu, the W. M. such as grade of this seminar Xu Wei in 2011; Han, F. F.; He, M.; Hu, D. Y.; He, J.; Yang, S.; Song B. A. Inhibition of Tobacco Bacterial Wilt with Sulfone Derivatives Containing an 1,3,4-Oxadiazole Moiety.
j. Agric. Food Chem.
201260,1036-1041.) to report with substituted benzoic acid be raw material, by etherificate, esterification, react with hydrazine hydrate, salify, closed loop, thioetherification, oxidation reaction synthesize and a series ofly contain 1,3,4-oxadiazole sulfone derivatives, wherein compound 2-phenyl-5-ethyl sulfone-1,3,4-oxadiazole, 2-(2,4-difluorophenyl)-5-ethyl sulfone-1,3,4-oxadiazole, 2-(3-fluorophenyl)-5-ethyl sulfone-1,3,4-oxadiazole and 2-(4-fluorophenyl)-5-ethyl sulfone-1,3,4-oxadiazole are to concentration (EC in the suppression of tobacco bacterial wilt pathogen
50) be respectively 39.8 ± 4.9,60.3 ± 2.8,47.9 ± 3.3 and 32.1 ± 2.3
μg/mL, and commercial References medicament can kill 3000 EC
50be 45.9 ± 6.6
μg/mL.(Li, the P. such as this seminar Li Pei in 2013; Yin, J.; Xu, W. M.; Wu, J.; He, M.; Hu, D. Y.; Yang, S.; Song B. A. Synthesis, Antibacterial Activities, and 3D-QSAR of Sulfone Derivatives Containing 1,3,4-Oxadiazole Moiety.
chem. Biol. Drug Des.
2013, 82,546 – 556.) and be raw material with substituted benzoic acid, also design and synthesis a series of newly containing 1,3,4-oxadiazole sulfone derivatives, determines its biologically active to the bacterial disease such as tobacco bacterial wilt, bacterial wilt of tomato pathogen, find wherein compound 2-(4-fluorophenyl)-5-methyl sulfone-1,3,4-oxadiazole, 2-phenyl-5-methyl sulfone-1,3,4-oxadiazole is best to the activity of tobacco bacterial wilt, bacterial wilt of tomato pathogen respectively, EC
50value is respectively 8.29 ± 0.56,19.77 ± 0.75
μg/mL.
Based on previous work, we to this seminar early stage synthesized by sulfone compound carry out further structure of modification, substituted benzene ring has been changed into substituted benzyl, and turbidity method is adopted to the compound of synthesis, carry out bioactivity screening for citrus bacterial canker disease, soft rot of cabbage pathogen, result shows that part of compounds all has good inhibit activities to citrus bacterial canker disease and soft rot of cabbage pathogen.
Summary of the invention
The object of the invention is, based on previous work, further structure of modification is carried out to synthesized 1,3, the 4-oxadiazole sulfone derivatives that has, filtered out, to citrus bacterial canker disease and soft rot of cabbage pathogen, there is better active compound.
The present invention has the application of 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives of control crop bacterial disease, and its derivative has following general formula:
Formula (I)
In formula (I): R
1be selected from hydrogen, halogen; R
2be selected from methyl, ethyl.
Particular compound is:
Compound
a: 2-benzyl-5-methylsulfonyl-1,3,4-oxadiazole;
Compound
b: 2-benzyl-5-ethyl sulfone-1,3,4-oxadiazole;
Compound
c: 2-(4-luorobenzyl)-5-methylsulfonyl-1,3,4-oxadiazole;
Compound
d: 2-(4-luorobenzyl)-5-ethyl sulfone-1,3,4-oxadiazole;
Compound
e: 2-(2,4-dichloro benzyl)-5-methylsulfonyl-1,3,4-oxadiazole;
Compound
f: 2-(2,4-dichloro benzyl)-5-ethyl sulfone-1,3,4-oxadiazole;
Above-claimed cpd be used for the citrus bacterial canker disease of crop bacterial disease prevented and treated and soft rot of cabbage, demonstrate high activity.
The synthetic method bibliography of above-claimed cpd: 1. Xu, W. M.; He, J.; He, M.; Han, F. F.; Chen, X. H.; Pan, Z. X.; Wang, J.; Tong, M. G. Synthesis and antifungal activity of novel sulfone derivatives containing 1,3,4-oxadiazole moieties.
molecules 2011, 16,9129-9141. is Li 2., P.; Yin, J.; Xu, W. M.; Wu, J.; He, M.; Hu, D. Y.; Yang, S.; Song B. A. Synthesis, antibacterial activities, and 3D-QSAR of sulfone derivatives containing 1,3,4-oxadiazole moiety.
chem. Biol. Drug Des.
2013, 82,546 – 556. 3. Xu, W. M.; Li, S. Z.; He, M.; Yang, S.; Li, X. Y.; Li, P. Synthesis and bioactivities of novel thioether/sulfone derivatives containing 1,2,3-thiadiazole and 1,3,4-oxadiazole/thiadiazole moiety.
bioorg. Med. Chem. Lett.
2013, 23,5821 – 5824. 4. Li, P.; Shi, L.; Yang, X.; Yang, L.; Chen, X. W.; Wu, F.; Shi, Q. C.; Xu, W. M.; He, M.; Hu, D. Y.; Song, B. A. Design, synthesis, and antibacterial activity against rice bacterial leaf blight and leaf streak of 2,5-substituted-1,3,4-oxadiazole/thiadiazole sulfone derivative.
bioorg. Med. Chem. Lett.
2014, 24,1677 – 1680.
The application with 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives of control crop bacterial disease of the present invention is medicine or medicament for the preparation of preventing and treating citrus bacterial canker disease and soft rot of cabbage.
The application with 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives of control crop bacterial disease of the present invention, described compound is to concentration EC in the suppression of citrus bacterial canker disease pathogen
50the scope of value is: 1.23 ~ 30.10
μg/mL, to the EC of Chinese cabbage soft rot nosophyte
50the scope of value is: 29.56 ~ 79.08
μg/mL, far exceedes existing commercial References medicament Yekuzuo and Thiodiazole-copper.
2, the 5-substituting groups-1,3 with control crop bacterial disease of the present invention, the application of 4-oxadiazole sulfone derivatives, wherein compound 2-(4-luorobenzyl)-5-methylsulfonyl-1,3,4-oxadiazole is to the EC of citrus bacterial canker disease pathogen and soft rot of cabbage pathogen
50value is respectively 1.23 and 29.56
μg/mL, control efficiency is best.
Invention effect:
1. the present invention 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives is applied to control crop bacterial disease, especially mainly prevents and treats citrus bacterial canker disease, soft rot of cabbage disease, shows very high activity.
2. 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives are applied to control crop bacterial disease, and specifically, can prevent and treat citrus bacterial canker disease, soft rot of cabbage disease, effect is far more than existing commercial References medicine Yekuzuo and Thiodiazole-copper.
3. 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives are applied to control crop bacterial disease, and structure is simple, and preparation technology is simple, and production cost is low, have a extensive future for the preparation of the medicine of control citrus bacterial canker disease, soft rot of cabbage disease or medicament.
Embodiment
Embodiment one: the indoor suppression citrus bacterial canker disease of part of compounds and the determination of activity of soft rot of cabbage pathogen
Experimental technique
By citrus bacterial canker disease and soft rot of cabbage pathogen at NB(beef extract: 3 g, peptone: 5 g, yeast extract: 1 g, glucose: 10 g, agar: 18 g, intermediate water: 1 L; About pH=7,121 DEG C of sterilizing 20 min are adjusted with 5 mol/L NaOH solution) rule above solid culture medium, cultivate until grow single bacterium colony at 30 DEG C.On picking NB solid culture medium, citrus bacterial canker disease and the single bacterium colony of soft rot of cabbage pathogen are to NB liquid nutrient medium (beef extract: 3 g, peptone: 5 g, yeast extract: 1 g, glucose: 10 g, intermediate water: 1 L; With 5 mol/L NaOH solution adjust about pH=7,121 DEG C of sterilizing 20 min) in, 28 DEG C, 180 rpm constant-temperature table shaken cultivation to grow logarithmic phase for subsequent use.
It is 200,100 that synthesized compound and commercial References medicament are mixed with concentration respectively
μthe pastille NB liquid nutrient medium of g/mL, adds 40
μthe NB liquid nutrient medium containing citrus bacterial canker disease and soft rot of cabbage pathogen of the above-mentioned preparation of L, at 30 DEG C, 180 rpm constant-temperature table shaken cultivation 24 ~ 48 h, measures OD value (OD by the bacterium liquid of each concentration in microplate reader
595).And measuring concentration is in addition 200,100
μthe NB liquid nutrient medium OD value of g/mL medicament and contrast medicament, corrects the OD value that medicament itself causes.The computing formula correcting OD value and inhibiting rate is as follows:
Correction OD value=containing bacterium culture medium OD value-aseptic culture medium OD value;
Inhibiting rate=(control medium bacterium liquid OD value after correcting-correct toxic medium OD value)/correct rear control medium bacterium liquid OD value × 100%;
Measure according to above method, the inhibit activities of partial target compound is shown in
table 1with
table 2.
By
table 1with
table 2can find out: at the concentration tested, target compound all has certain inhibit activities to citrus bacterial canker disease or soft rot of cabbage pathogen.200 and 100
μunder g/mL concentration, the compound tested
a, b, c, d, eand
f100% is to the inhibiting rate of citrus bacterial canker disease pathogen, compound
cand
e100% is to the inhibiting rate of Chinese cabbage soft rot nosophyte, is all better than contrast medicament Yekuzuo and Thiodiazole-copper.Because 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives structures in the present invention are closely similar, other compounds can be predicted also there is certain suppression citrus bacterial canker disease and the effect of soft rot of cabbage pathogen.
Embodiment two: high-activity compound virulence regression equation and concentration (EC in suppressing
50) mensuration of value
The compound of synthesis and contrast medicament are mixed with respectively the toxic NB liquid nutrient medium of 5 respective concentration, get 5 mL in test tube, measure pastille aseptic liquid nutrient medium OD value (OD by microplate reader
595), add 40
μl contains the NB liquid nutrient medium of citrus bacterial canker disease or soft rot of cabbage pathogen, then at 30 DEG C, 180 rpm constant-temperature table shaken cultivation 24 ~ 48 h, measures the OD value (OD of each concentration bacterium liquid by microplate reader
595).And the OD value of each concentration bacterium liquid, corrects the OD value caused due to medicament itself after measuring the OD value and 24 ~ 48 h contrasting the aseptic NB liquid nutrient medium of medicament pastille in addition.Inhibiting rate data are converted to probit value (
y), drug concentration (
μg/mL) convert to logarithm value (
x), in Excel data processing software, carry out regression analysis, obtain virulence regression equation (
y=a
x+ b) and correlation coefficient (
r), calculate medicament to pathogen EC
50value, the results are shown in
table 3with
table 4.
table 3part of compounds is to the EC of citrus bacterial canker disease pathogen
50value
Note:
a 90% effective content;
b 20% suspending agent, in an experiment, is all scaled effective content and tests.
From
table 3in can find out: target compound
a,
b,
c,
d,
eand
fto the EC of citrus bacterial canker disease pathogen
50value is respectively 6.52 ± 1.19,27.80 ± 2.76,1.23 ± 0.97,16.16 ± 2.21,2.47 ± 0.69 and 30.10 ± 3.87
μg/mL, is better than commercially available medicine contrast medicament Yekuzuo and Thiodiazole-copper, EC
50value is respectively 58.21 ± 2.77,77.04 ± 1.96
μg/mL.Can find out that compound 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives has good inhibit activities to citrus bacterial canker disease pathogen.
table 4part of compounds is to the EC of Chinese cabbage soft rot nosophyte
50value
Note:
a 90% effective content;
b 20% suspending agent, in an experiment, is all scaled effective content and tests.
From
table 4in can find out: target compound
a,
b,
c,
d,
eand
fto the EC of Chinese cabbage soft rot nosophyte
50value is respectively 33.06 ± 1.34,53.68 ± 2.23,29.56 ± 1.91,57.09 ± 3.84,46.84 ± 4.82 and 79.08 ± 4.12
μg/mL, is better than commercially available medicine contrast medicament Yekuzuo and Thiodiazole-copper, its EC
50value is respectively 151.66 ± 5.98 and 269.80 ± 7.11
μg/mL.Can find out that compound 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives has good inhibit activities to Chinese cabbage soft rot nosophyte.
Claims (4)
1. have the application of 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives of control crop bacterial disease, its derivative has following general formula:
Formula (I)
In formula (I): R
1be selected from hydrogen, halogen; R
2be selected from methyl, ethyl,
Particular compound is:
Compound
a: 2-benzyl-5-methylsulfonyl-1,3,4-oxadiazole;
Compound
b: 2-benzyl-5-ethyl sulfone-1,3,4-oxadiazole;
Compound
c: 2-(4-luorobenzyl)-5-methylsulfonyl-1,3,4-oxadiazole;
Compound
d: 2-(4-luorobenzyl)-5-ethyl sulfone-1,3,4-oxadiazole;
Compound
e: 2-(2,4-dichloro benzyl)-5-methylsulfonyl-1,3,4-oxadiazole;
Compound
f: 2-(2,4-dichloro benzyl)-5-ethyl sulfone-1,3,4-oxadiazole;
It is characterized in that above-claimed cpd is used for preventing and treating citrus bacterial canker disease and soft rot of cabbage, demonstrate high activity.
2. the application with 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives of control crop bacterial disease according to claim 1, is characterized in that: for the preparation of medicine or the medicament of preventing and treating citrus bacterial canker disease and soft rot of cabbage.
3. the application with 2,5-substituting group-1,3,4-oxadiazole sulfone derivatives of control crop bacterial disease according to claims 1 to 2, is characterized in that: compound is to concentration EC in the suppression of citrus bacterial canker disease pathogen
50the scope of value is: 1.23 ~ 30.10
μg/mL, to the EC of Chinese cabbage soft rot nosophyte
50the scope of value is: 29.56 ~ 79.08
μg/mL, far exceedes existing commercial References medicament Yekuzuo and Thiodiazole-copper.
4. according to claims 1 to 2 have 2 of control crop bacterial disease, 5-substituting group-1,3, the application of 4-oxadiazole sulfone derivatives, it is characterized in that: compound 2-(4-luorobenzyl)-5-methylsulfonyl-1,3,4-oxadiazole is to the EC of citrus bacterial canker disease pathogen and soft rot of cabbage pathogen
50value is respectively 1.23 and 29.56
μg/mL, control efficiency is best.
?
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Cited By (1)
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| CN107056773A (en) * | 2017-04-24 | 2017-08-18 | 贵州大学 | Pyrazoles Lian Evil containing pyridiniujm（Thiophene）Diazoles compound and preparation method and application |
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| GB2380190A (en) * | 2001-08-28 | 2003-04-02 | Bayer Ag | Antiinflammatory heterocyclic sulphones |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107056773A (en) * | 2017-04-24 | 2017-08-18 | 贵州大学 | Pyrazoles Lian Evil containing pyridiniujm（Thiophene）Diazoles compound and preparation method and application |
| CN107056773B (en) * | 2017-04-24 | 2020-07-14 | 贵州大学 | Pyrazole dioxa (thia) diazole compound containing pyridinium salt and preparation method and application thereof |
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