CN102757400A - 2, 5-substituent group oxazole derivative and applications thereof - Google Patents
2, 5-substituent group oxazole derivative and applications thereof Download PDFInfo
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- CN102757400A CN102757400A CN201210247616XA CN201210247616A CN102757400A CN 102757400 A CN102757400 A CN 102757400A CN 201210247616X A CN201210247616X A CN 201210247616XA CN 201210247616 A CN201210247616 A CN 201210247616A CN 102757400 A CN102757400 A CN 102757400A
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Abstract
The invention discloses a 2, 5-substituent group oxazole derivative capable of preventing crop diseases. The derivative can effectively prevent speckled type bacteriosis, leaf blight type bacteriosis, withered type bacteriosis, ulcerative type bacteriosis, rotten type bacteriosis, dysplastic type bacteriosis and other bacteriosis. The 2, 5-substituent group oxazole derivative is used for preventing crop diseases, is of a novel structure, can not generate cross resistance with the conventional pesticides as oxazole sulfone compounds are not available on the pesticide market. The 2, 5-substituent group oxazole derivative has bright application prospect.
Description
Technical field
The present invention relates to chemical industry and agricultural chemicals, concrete technology is 2,5-Qu Dai Ji oxazole analog derivative and application thereof.
Background technology
To the great disease problem of agricultural, carry out guide's Study on Structure Optimizing of disease regulation and control, scientific and efficient ground is found safety and green candidate's agricultural chemicals of potential market vitality is arranged is the vital task that faces in China's novel pesticide initiative fundamental research.The guide finds it is the key that realizes innovation Green Chemistry agricultural chemicals, and design optimization synthesizes some types of agricultural chemicals elder generation guide structures, develops the Green Chemistry agricultural chemicals of novel low toxicity, low residue, safety, seems very urgent and important.This seminar was an initiation material with the lead compound gallic acid that filters out in the natural products in 2007, and design is synthetic a series ofly new to contain 1,3,4-thiophene (evils) di azoly sulfone (sulfoxide) derivative, the employing growth rate method, with fusarium graminearum (
Gibberella zeae), botrytis cinerea pers (
Botrytis cinerea), Sclerotinia sclerotiorum (
Sclerotinia sclerotiorum) etc. disease be tested object, the part target compound has been carried out bacteriostatic activity research.The result shows, its EC of part target compound
50Value is at 2.9-23.3
mBetween the g/mL, have the good restraining disease active [
Bioorg. Med. Chem. 2007,
15, 3981;
Bioorg. & Med. Chem.
2008, 16,3632.].Patent US 5166165 report series compound ⅰ have the effect of better inhibited fungi, under 100 ppm concentration, the grey mould fruit rot of strawberry bacterium are had better inhibited activity like active best compound ⅰ a and ⅰ b in this patent.
But this type of compound water soluble is poor, desirable not enough aspect the inhibition of disease.The present invention carries out conversion to the compound skeleton on the forefathers basis, synthetic one type contains 2,5-Qu Dai Ji oxazole analog derivative, and explore its activity.It is active preferably that the result shows that the compound that is obtained not only has common fungal disease, simultaneously Micobial Disease also had good active.
Summary of the invention
The objective of the invention is on the forefathers basis, the skeleton of background compound is carried out conversion, synthetic one type contains 2,5-Qu Dai Ji oxazole analog derivative, and explore its activity.Study to common fungal disease with to the activity of Micobial Disease.
The present invention contains 2, and 5-Qu Dai Ji oxazole analog derivative has following general formula:
Formula (I)
It is characterized in that in the formula (I):
R is trifluoromethyl, C1-C5 alkyl, C1-C5 haloalkyl;
R
1Be halogen atom, itrile group, nitro, C1-C5 alkyl, C1-C3 alkoxyl group.
Said C1-C5 alkyl is methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl or neo-pentyl; Said C1-C5 haloalkyl is fluoroform alkyl, methyl chlorofluoride base, trichloromethane base, methylene fluoride base, methylene chloride-based, 1; 2-C2H4F2 C2H4F2 base, 1; 2-Tetrafluoroethane base, 1,2-ethylene dichloride base or 1,2-tetrachloroethane base; Said halogen atom is fluorine, chlorine, bromine or iodine, and said C1-C3 alkoxyl group is methoxyl group, oxyethyl group or positive propoxy.
The compounds of this invention is 2-methylsulfonyl-5-(3-chloro-phenyl-)-oxazoles, 2-methylsulfonyl-5-benzyl-oxazoles, 2-methylsulfonyl-5-(3-fluorophenyl)-oxazoles, 2-methylsulfonyl-5-(3, the 4-Dimethoxyphenyl)-oxazoles, 2-methylsulfonyl-5-(2-chloro-phenyl-)-oxazoles, 2-methylsulfonyl-5-(2-trifluoromethyl)-oxazoles.
Describedly contain 2; The application of 5-Qu Dai Ji oxazole analog derivative, it is characterized in that described 2,5-Qu Dai Ji oxazole analog derivative as Fungicidal compounds as suppressing Plant diseases; Active ingredient 2, the weight percentage of 5-Qu Dai Ji oxazole analog derivative is 0.1%-89%.
Described Plant diseases is head blight, hypochnus, late blight, stripe rust.
Described Plant diseases is fusarium graminearum, Rhizoctonia solani Kuhn, the late blight of potato, stripe rust of wheat.
Described Plant diseases is a crop Micobial Disease.
Said crop Micobial Disease is withered type Micobial Disease of leaf and blue or green withered type Micobial Disease.
Said Micobial Disease is the bacillary leaf blight of bacterial blight of rice, cucumber, the bacillary leaf blight of konjaku, Folium Cucumidis sativi rot, tobacco bacterial wilt, bacterial wilt of tomato, potato bacterial wilt, strawberry bacterial wilt, pepper ralstonia solanacearum or eggplant bacterial wilt.
Said compound is used to handle material, plant, zone, soil, seed, the space of fungi or bacterium, fungi or bacterium habitat.
Embodiment
Embodiment one: the preparation of target compound
With compound 2-methylsulfonyl-5-(2; The 4-dichlorophenyl) preparation of this target compound of the preparation of-oxazoles and 2-methylsulfonyl-5-Ben Ji oxazole explanation; Wherein bromoacetophenone and 2,4 dichloro benzene ethyl ketone, 2-amino-methyl phenyl ketone hydrochloride and 2-amino-2,4 dichloro benzene acetophenone hydrochloride, 5-phenyl-2-Qiu Ji oxazole and 5-(2; The 4-dichlorophenyl)-and the synthetic of 2-Qiu Ji oxazole all is with reference to existing document, carried out necessary variation and prepared.R
1Group is not limited to cited 2; 4-dichloro and hydrogen; Also methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, neo-pentyl, fluoroform alkyl, methyl chlorofluoride base, trichloromethane base, methylene fluoride base, methylene chloride-based, a fluoromethane base, 1; 2-C2H4F2 C2H4F2 base, 1; 2-Tetrafluoroethane base, 1; 2-ethylene dichloride base, 1, groups such as 2-tetrachloroethane base, fluorine, chlorine, bromine, iodine, vinyl, propenyl, allyl group, crotonyl, isobutenyl, pentenyl, isopentene group, new pentenyl, methyl-formiate base, group-4 ethyl formate, propyl formate base, methoxyl group, oxyethyl group or positive propoxy.
, bromoacetophenone and 2,4-dichloro bromoacetophenone synthetic
In 250 mL there-necked flasks, add 2,4 dichloro benzene ethyl ketone or methyl phenyl ketone (0.53mmol), anhydrous diethyl ether 150 mL.After stirring treated that solid all dissolves, cryosel was bathed to-3 С, slow dripping bromine (0.58mmol), and insulation dropwised about 0 С in 4 hours in the dropping process.TCL tracking reaction (
V Methylene dichloride:
V Sherwood oil=8:1), treat that raw material disappears the back with saturated aqueous common salt (150mL * 3) washing, wash with saturated sodium sulfite solution then, treat organic phase become colorless after standing demix.Separatory, anhydrous sodium sulfate drying, ether is taken off in decompression, and the absolute ethyl alcohol recrystallization freezes crystalline substance in refrigerator and cooled.Yield 84%.Bromoacetophenone fusing point: 48 ~ 51 С, 2,4-dichloro bromoacetophenone fusing point: 19 ~ 21 С.
, 2-amino-methyl phenyl ketone hydrochloride and 2-amino-2,4 dichloro benzene acetophenone hydrochloride synthetic
Bromoacetophenone (2,4 dichloro benzene ethyl ketone) (0.01 mol) and hexamethylenetetramine (1.5 g, 0.011 mol) are dissolved in respectively in the 15 mL chloroforms, then with its mixing, stirring at room 4 h, TLC tracking reaction (
V Methylene dichloride:
V Sherwood oil=5:1), be cooled to 0 ℃, to filter, oven dry gets white solid.Under agitation condition, the gained solid is joined in the 20 mL ethanolic solns of 4 mL concentrated hydrochloric acids, room temperature reaction 48 h filter, and boil off ethanol, use ethyl alcohol recrystallization, get white crystal, productive rate 73.5%.2-amino-methyl phenyl ketone hydrochloride fusing point: 213 ~ 215 С, yield 71%.2-amino-methyl phenyl ketone hydrochloride fusing point: 213 ~ 214 С, yield 68%.
, 5-phenyl-2-Qiu Ji oxazole and 5-(2,4 dichloro benzene base)-2-Qiu Ji oxazole synthetic
With K
2CO
3(1.05 mmol) is dissolved in the 3 mL water, joins in ethanol (10 mL) solution of 2-amino-methyl phenyl ketone hydrochloride (1 mmol) or 2-amino-2,4 dichloro benzene acetophenone hydrochloride (1 mmol) and CS2 (20 mmol) backflow 18h slowly; Filter, add 3 mL Glacial acetic acid min. 99.5 in the filtrating, pour into behind the stirring at room 1h in the 50mL frozen water, separate out a large amount of solids; Suction filtration is used washing with alcohol, infrared drying; Obtain yellow solid, productive rate 66.2%, m.p. 124 ~ 127 С.
, 5-phenyl-2-Jia Liu Ji oxazole and 5-(2,4 dichloro benzene base)-2-Jia Liu Ji oxazole synthetic
In 50 mL flasks, add 5-phenyl-2-Qiu Ji oxazole or 5-(2,4 dichloro benzene base)-2-Qiu Ji oxazole (0.01 mol), NaOH (0.04 g, 0.01 mol) and 10 mL water successively, the dissolving back adds methyl-sulfate (1.26g, 0.01 mol).Room temperature reaction 1 hour is taken out rate, and the absolute ethyl alcohol recrystallization gets product, and infrared drying gets product.5-phenyl-2-Jia Liu Ji oxazole, 54 ~ 56 ℃ of fusing points, 1H NMR (500 MHz, CDCl
3) δ: 7.64 ~ 7.23 (m, 6H, ArH and oxazole-H), 2.54 (s, 3H, CH3); 5-(2,4 dichloro benzene base)-2-Jia Liu Ji oxazole, 66 ~ 68 ℃ of fusing points.Yield 80%, 1H NMR (500 MHz, CDCl
3) δ: 8.03 ~ 7.51 (m, 4H, ArH and oxazole-H), 2.59 (s, 3H, CH
3).
, 5-phenyl-2-methylsulfonyl and 5-(2,4 dichloro benzene base)-2-first Feng Ji oxazole synthetic
Throw sulfide compound (5.23 mmol), Glacial acetic acid min. 99.5 15 mL add KMnO after the stirring and dissolving in the there-necked flask of 50 mL band prolong
4(1.06g, 6.7 mmol).Add an amount of saturated sodium sulfite anhy 96 after reaction finishes, pour into and promptly separate out white solid in the frozen water, filter the back ethyl alcohol recrystallization and get sulfone class targets compound.
Methylsulfonyl-5-Ben Ji oxazole
Clear crystal, m.p. 114 ~ 115 С; Yield 82.8%;
1H NMR (500 MHz, CDCl
3)
δ:7.29 ~ 7.59 (m, 6H, ArH and oxazole-H), 2.69 (s, 3H, CH
3);
13C NMR (125 MHz, CDCl
3)
δ:156.70,154.97,130.33,129.24,128.86,125.98,125.23,123.09,122.91,42.66; IR (KBr, cm
-1)
ν:3033,2934,1601,1573,1371,1155; Anal. Calcd for C
10H
9NO
3S:C 53.80, and H 4.06, and N 6.27; Found:C 53.52, and H 4.04, N 6.45.
2-methylsulfonyl-5-(2,4 dichloro benzene base)-oxazoles
Clear crystal, m.p. 109 ~ 111 С; Yield 79.4%;
1H NMR (500 MHz, CDCl
3)
δ:7.49 ~ 7.97 (m, 4H, ArH and oxazole-H), 2.71 (s, 3H, CH
3);
13C NMR (125 MHz, CDCl
3)
δ:158.74,156.86,131.71,128.15,128.86,126.32,125.53,121.76,121.23,43.34; IR (KBr, cm
-1)
ν:3039,2942,1616,1573,1373,1143; Anal. Calcd for C
10H
7Cl
2NO
3S:C 41.11, and H 2.42, and N 4.79; Found:C 41.46, and H 2.68, N 4.53.
According to identical method, change substrate, obtain compound as
Table 1,The hydrogen spectrogram of part of compounds as
Table 2
The yield of table 1 part of compounds
| Compound | Yield |
| 2-methylsulfonyl-5-(3-chloro-phenyl-)-oxazoles | 65 |
| 2-methylsulfonyl-5-benzyl-oxazoles | 77 |
| 2-methylsulfonyl-5-(3-fluorophenyl)-oxazoles | 76 |
| 2-methylsulfonyl-5-(3, the 4-Dimethoxyphenyl)-oxazoles | 67 |
| 2-methylsulfonyl-5-(2-chloro-phenyl-)-oxazoles | 47 |
| 2-methylsulfonyl-5-(2-trifluoromethyl)-oxazoles | 56 |
The hydrogen spectrum of table 2 part of compounds
| Compound | 1H NMR(500 MHz, CDCl 3) δ |
| 2-methylsulfonyl-5-(3-chloro-phenyl-)-oxazoles | 7.13~7.59 (m, 5H, ArH and oxazole-H ), 2.67 (s, 3H, CH 3) |
| 2-methylsulfonyl-5-(3-fluorophenyl)-oxazoles | 7.07~7.65 (m, 5H, ArH and oxazole-H ), 2.71 (s, 3H, CH 3) |
| 2-methylsulfonyl-5-(3, the 4-Dimethoxyphenyl)-oxazoles | 7.21~7.79 (m, 4H, ArH and oxazole-H ), 2.71 (s, 3H, CH 3) |
| 2-methylsulfonyl-5-(2-chloro-phenyl-)-oxazoles | 7.20~7.69 (m, 5H, ArH and oxazole-H ), 2.70 (s, 3H, CH 3) |
| 2-methylsulfonyl-5-(2-trifluoromethyl)-oxazoles | 7.14~7.74(m, 5H, ArH and oxazole-H ), 2.68 (s, 3H, CH 3) |
Embodiment two: the bacteriostatic activity experiment of part of compounds
Adopt the isolated growth rate method to measure the bacteriostatic activity of compound.Heating potato dextrose agar (PDA substratum: yam 200 g, agar 20 g, glucose 20 g, zero(ppm) water 1000 mL) is to the state of dissolving (40-60 С); 10 mL soups (soups of 10 times of final concentrations) are poured in the 90 mL PDA substratum; Fully shake up; Evenly pour in the petridish of diameter 9 cm horizontal positioned, to be cooled solidifying into.Use punch tool to play the bacterium dish that cut-off directly is 4 mm at the fresh pathogenic bacteria colony edge of cultivating 4 d; The bacterium dish is inverted in contains the dull and stereotyped central authorities of medicament PDA; Placing 27 С fixed temperature and humidity incubators to be inverted then cultivates; Begin observation when treating the blank colony growth extremely near plate 2/3rds places, the right-angled intersection method is measured colony diameter, averages.Blank is adding medicine not, but contains the solvent and 0.5% Tween 20 of same concentration, every processing triplicate.Calculate the inhibiting rate of medicament through following formula to mycelial growth:
I(%)=(C-T)/(C-0.4)*100%
Wherein I is an inhibiting rate, and C is blank diameter (cm), and T is for handling diameter (cm).
Table 3 part of compounds is bacteriostatic activity data (inhibiting rate) under 50 μ g/mL concentration
Annotate: the every processing triplicate of a
B with commodity medicament thiophanate_methyl, dislike mould spirit, nitrile bacterium azoles as positive control drug
From
Table 3Giving birth to survey active testing result can find out, 50
μUnder the g/mL concentration, compound 2-methylsulfonyl-5-benzene base oxazole to gibberella saubinetii cause of disease bacterium (
G. zeae), the capsicum withered pathogenic bacteria (
F. oxysporum) and apple decay cause of disease bacterium (
C. mandshurica) bacteriostatic activity better, its inhibiting rate is respectively 71.0%, 58.4% and 64.3%, its activity slightly is superior to commodity compound and dislikes mould spirit (59.3%, 61.5%, 59.5%).Compound 2-methylsulfonyl-5-(2,4 dichloro benzene base)-oxazole to gibberella saubinetii cause of disease bacterium (
G. zeae), the capsicum withered pathogenic bacteria (
F. oxysporum) and apple decay cause of disease bacterium (
C. mandshurica) inhibiting rates of three kinds of fungies is respectively 65.4%, 63.7% and 57.0%, its activity is superior to or is equivalent to contrasting medicament and dislikes mould spirit.
The determination of activity of the indoor inhibition bacterial wilt of embodiment three: oxazole sulfone compounds
TP:
The bacterial wilt pathogenic bacteria is rule above the solid medium at NA (peptone 5g, yeast powder 1g, glucose 10g, agar 18g, zero(ppm) water 1L, PH 7.0-7.2), under 28 C, cultivate up to growing single bacterium colony.The single bacterium colony of bacterial wilt pathogenic bacteria is to liquid NA substratum on the picking NA solid medium, and is subsequent use to logarithmic phase at 30 C, 180 rpm constant temperature shaking table shaking culture.
Medicament and contrast medicament are configured to the toxic NB that concentration is 500,200 mg/L (beef peptone 3 g, peptone 5 g, yeast powder 1 g, glucose 10 g, zero(ppm) water 1 L, PH 7.0-7.2) liquid nutrient medium respectively, get 5 mL to test tube, add 40
μL contains the NA liquid nutrient medium of bacterial wilt germ, 30 C, 180 rpm constant temperature shaking table shaking culture 2 days, the bacterium liquid of each concentration is measured OD value (600 nm) on spectrophotometer.And measuring concentration in addition is the NB liquid nutrient medium OD value of 500,200 mg/L medicaments and contrast medicament, and the OD value that medicament itself causes is proofreaied and correct.The calculation formula of proofreading and correct OD value and preventive effect is following:
Proofread and correct OD value=contain bacterium culture medium OD value-aseptic culture medium OD value
Preventive effect %=(proofreading and correct the back control medium bacterium liquid OD value-toxic substratum OD of correction value)/control medium bacterium liquid OD value * 100 after proofreading and correct
Measure according to above method, the inhibition activity of part target compound is seen
Table 4
Table 4.Bu Fen oxazole sulfone compound is active to the inhibition of tobacco Ralstonia solanacearum
Annotate:
aE.I.Du Pont Company produces, and 46.1% effective content in experiment, all is scaled effective content and experimentizes.
By
Table 4The result knows that under test concentrations, target compound all has certain inhibition activity to tobacco bacterial wilt.500
μG/mL and 200
μUnder the g/mL concentration, the compound of being tested is about 100% to the inhibiting rate of tobacco bacterial wilt.Because Zhong De oxazole sulfone compound structure of the present invention is closely similar, predictable, other compounds also have the effect of certain control tobacco bacterial wilt.Because the cause of disease of tobacco bacterial wilt has identical cause of disease with bacterial wilt of tomato, potato bacterial wilt, strawberry bacterial wilt, pepper ralstonia solanacearum or eggplant bacterial wilt; All belong to blue or green withered type Micobial Disease ， Gu oxazole sulfone compound and also can prevent and treat other blue or green withered type Micobial Disease.
Embodiment four: high-activity compound virulence regression equation and EC
50The mensuration of value
Medicament and contrast medicament are configured to the toxic NB liquid nutrient medium that concentration is 200,100,50,25,12.5 and 6.25 mg/L respectively; Get 5 mL in test tube; Add 40 μ L and contain the NB liquid nutrient medium of bacterial wilt germ, then 30 C, 180 rpm constant temperature shaking table shaking culture 2 days.OD value (600 nm) with each concentration bacterium liquid of spectrophotometric determination; And measure concentration in addition and be the OD value of the toxic aseptic NB liquid nutrient medium of 200,100,50,25,12.5 and 6.25 mg/L medicaments and contrast medicament, the OD value that causes owing to medicament itself is proofreaied and correct.With the inhibiting rate data-switching become probit value (Y), drug concentration (
μG/mL) convert logarithmic value (X) to, in SPSS 11.5 softwares, carry out regression analysis, obtain virulence regression equation (Y=AX+B) and relation conefficient (r), calculate medicament concentration (EC in the pathogenic bacteria inhibition
50), the result sees
Table 2
Table 5Bu Fen oxazole sulfone compound is to concentration (EC in the inhibition of tobacco bacterial wilt
50 μG/mL)
Annotate:
aE.I.Du Pont Company produces, and 46.1% effective content in experiment, all is scaled effective content and compares.
By
Table 5The result knows the IC of compound 2-methylsulfonyl-5-Ben Ji oxazole to tobacco bacterial wilt
50Value is 38.5 μ g/mL; The commercial References medicament can kill in the inhibition of 3000 pairs of tobacco bacterial wilts concentration be 45.9 μ g/mL; Can find out that it is active that compound 2-methylsulfonyl-5-Ben Ji oxazole has an extraordinary inhibition to tobacco bacterial wilt, during it suppresses concentration be superior to killing 3,000.
Conclusion
1 one type 2,5-Qu Dai Ji oxazole analog derivative is applied to prevent and treat crop fungal disease, and is effective.
2 one type 2; 5-Qu Dai Ji oxazole analog derivative is applied to prevent and treat crop Micobial Disease; Specifically, can prevent and treat spotted type Micobial Disease, the withered type Micobial Disease of leaf, blue or green withered type Micobial Disease, withered type Micobial Disease, ulcer type Micobial Disease, the type Micobial Disease of rotting and deformity Micobial Disease.
3 one type 2,5-Qu Dai Ji oxazole analog derivative is applied to prevent and treat crop Micobial Disease, and novel structure, agricultural chemicals be Mei You oxazole sulfone compound on the market, therefore, can not produce cross resistance with existing agricultural chemicals.
One type 2,5-Qu Dai Ji oxazole analog derivative is applied to prevent and treat crop Micobial Disease, can be prepared into several formulations, is easy to be converted into practical application.
Claims (10)
1.2 5-Qu Dai Ji oxazole analog derivative has following general formula:
Formula (I)
It is characterized in that in the formula (I):
R is trifluoromethyl, C1-C5 alkyl, C1-C5 haloalkyl;
R
1Be halogen atom, itrile group, nitro, C1-C5 alkyl, C1-C3 alkoxyl group.
2. according to claim 12; 5-gets basic oxazole analog derivative of generation, it is characterized in that said C1-C5 alkyl is methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl or neo-pentyl, and said C1-C5 haloalkyl is fluoroform alkyl, methyl chlorofluoride base, trichloromethane base, methylene fluoride base, methylene chloride-based, 1; 2-C2H4F2 C2H4F2 base, 1; 2-Tetrafluoroethane base, 1,2-ethylene dichloride base or 1,2-tetrachloroethane base; Said halogen atom is fluorine, chlorine, bromine or iodine, and said C1-C3 alkoxyl group is methoxyl group, oxyethyl group or positive propoxy.
3. according to claim 12; 5-Qu Dai Ji oxazole analog derivative; It is characterized in that compound is 2-methylsulfonyl-5-(3-chloro-phenyl-)-oxazoles, 2-methylsulfonyl-5-benzyl-oxazoles, 2-methylsulfonyl-5-(3-fluorophenyl)-oxazoles, 2-methylsulfonyl-5-(3, the 4-Dimethoxyphenyl)-oxazoles, 2-methylsulfonyl-5-(2-chloro-phenyl-)-oxazoles, 2-methylsulfonyl-5-(2-trifluoromethyl)-oxazoles.
4. like claim 1 or 2 or 3 described 2; The application of 5-Qu Dai Ji oxazole analog derivative, it is characterized in that described 2,5-Qu Dai Ji oxazole analog derivative as Fungicidal compounds as suppressing Plant diseases; Active ingredient 2, the weight percentage of 5-Qu Dai Ji oxazole analog derivative is 0.1%-89%.
5. application according to claim 4 is characterized in that described Plant diseases is head blight, hypochnus, late blight, stripe rust.
6. application according to claim 5 is characterized in that described Plant diseases is fusarium graminearum, Rhizoctonia solani Kuhn, the late blight of potato, stripe rust of wheat.
7. application according to claim 4 is characterized in that described Plant diseases is a crop Micobial Disease.
8. application according to claim 7, said crop Micobial Disease are withered type Micobial Disease of leaf and blue or green withered type Micobial Disease.
9. application according to claim 8, said Micobial Disease are the bacillary leaf blight of bacterial blight of rice, cucumber, the bacillary leaf blight of konjaku, Folium Cucumidis sativi rot, tobacco bacterial wilt, bacterial wilt of tomato, potato bacterial wilt, strawberry bacterial wilt, pepper ralstonia solanacearum or eggplant bacterial wilt.
10. compound as claimed in claim 1 is used to handle material, plant, zone, soil, seed, the space of fungi or bacterium, fungi or bacterium habitat.
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| CN104557759A (en) * | 2013-10-17 | 2015-04-29 | 中国科学院大连化学物理研究所 | Method for preparing 5-sulfonyl methyl oxazole derivative |
| CN109566634A (en) * | 2017-09-28 | 2019-04-05 | 佛山市盈辉作物科学有限公司 | The synergistic composition of bacterium azoles is disliked containing fluorine ether bacterium amide and dichloro |
| CN110105347A (en) * | 2019-06-18 | 2019-08-09 | 浙江工业大学 | A kind of 2- (2- pyridyl group) -1,3- oxazole amide derivatives and its preparation method and application |
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| CN106614656A (en) * | 2016-12-17 | 2017-05-10 | 佛山市普尔玛农化有限公司 | Pesticide composition containing dichlorooxazole and ametoctradin |
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| 王振宁，等: "具有杀菌活性的噁唑类衍生物的研究进展", 《精细化工中间体》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104557759A (en) * | 2013-10-17 | 2015-04-29 | 中国科学院大连化学物理研究所 | Method for preparing 5-sulfonyl methyl oxazole derivative |
| CN109566634A (en) * | 2017-09-28 | 2019-04-05 | 佛山市盈辉作物科学有限公司 | The synergistic composition of bacterium azoles is disliked containing fluorine ether bacterium amide and dichloro |
| CN110105347A (en) * | 2019-06-18 | 2019-08-09 | 浙江工业大学 | A kind of 2- (2- pyridyl group) -1,3- oxazole amide derivatives and its preparation method and application |
| CN110105347B (en) * | 2019-06-18 | 2021-01-15 | 浙江工业大学 | 2- (2-pyridyl) -1, 3-oxazole amide derivative and preparation method and application thereof |
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