CN106243087B - A kind of triazole pyrrolidones series bactericidal agent, synthetic method and its application - Google Patents
A kind of triazole pyrrolidones series bactericidal agent, synthetic method and its application Download PDFInfo
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- CN106243087B CN106243087B CN201610817094.0A CN201610817094A CN106243087B CN 106243087 B CN106243087 B CN 106243087B CN 201610817094 A CN201610817094 A CN 201610817094A CN 106243087 B CN106243087 B CN 106243087B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Abstract
The invention belongs to field of chemical technology, especially a kind of triazole pyrrolidones as fungicide, the fungicide chemical structural formula is：Wherein, substituent R1And R2It is not fixed for phenyl or p-bromophenyl or rubigan or p-fluorophenyl or p-methylphenyl and other conjugated systems, substituting group position, number and conjugate position.Synthetic method obtains a kind of novel triazole pyrrolidones under the action of catalyst, ring-closure reaction to be condensed by intramolecular dehydration with a kind of triazolylamide ketone compounds.The new synthetic method that the present invention provides a kind of steps is few, yield is high is to synthesize a kind of novel triazole pyrrolidones, and it shows good bacteriostatic activity because of product, advantageous as the application of fungicide.
Description
Technical field
The present invention relates to field of chemical technology, especially a kind of triazole pyrrolidones series bactericidal agent and its synthesis side
Method.
Background technology
The problem of staple food supply deficiency is all the huge challenge that the mankind face all the time, and especially in Africa etc., agricultural is not sent out
Up to area.And the grain drop in production as caused by various bacteriums and fungus-caused corps diseases, the economic loss brought are very huge
Greatly.In order to cope with the demand under the bacterium constantly to make a variation and fungi and various different conditions to fungicide using limitation, research
The more new type bactericide with more preferable bacteriostatic activity is developed, is the key that promote fungicide development.Three be commercialized at present
Azoles fungicide is mainly characterized in that：The pharmacophore triazole ring of most of fungicide is all connected in carbochain, and is contained in molecular structure
There is the fungicide of amido bond to have very much, but the rarely found report containing amido bond in triazole bactericidal agent molecular structure.At present
Commercialized fungicide there are bacteriostatic activities not ideal enough, 503nhibiting concentration (IC50) it is higher the problems such as.
Invention content
The main purpose of the present invention is to provide a kind of triazole pyrrolidones series bactericidal agent and its synthetic methods.
Technical scheme is as follows：
A kind of triazole pyrrolidones series bactericidal agent, the fungicide chemical structural formula are：
Wherein, substituent R1And R2For phenyl or p-bromophenyl or rubigan or p-fluorophenyl or p-methylphenyl and its
His conjugated system, substituting group position, number and conjugate position are not fixed.
The method of the synthesis triazole pyrrolidones series bactericidal agent, the method includes following synthesis paths：
It the described method comprises the following steps：
1) mixed solvent is prepared in reaction bulb, mixed solvent is mixed in a certain ratio by ethyl alcohol and water；
2) compound 1 is added in the in the mixed solvent into the step 1), and reaction system is placed in 0~60 DEG C by potassium carbonate
Under be stirred to react 0.2~2 hour, until system in there are a large amount of solids；
The compound 1 is triazole acyl ammonia ketones derivant；
3) the reaction solution TLC monitorings of the step 2) is taken to filter, residue is through drying to obtain chemical combination after completion of the reaction
Object 2；
Complete the synthesis of triazole pyrrolidones series bactericidal agent.
The volume ratio that the step 1) prepares ethyl alcohol and water that mixed solvent uses is 1:1.The mixing prepared in this ratio
Solvent, dissolubility is preferable, is conducive to the progress of reaction.
Step 2) the compound 1 is 2 with potassium carbonate rate of charge:3.In this ratio be added potassium carbonate, then rapid reaction and
It is steady to carry out.The excessively few then reaction of potassium carbonate addition is slowly carried out or is not reacted, and crossing at most causes reaction violent, and by-product increases
It is more.
Step 2) the reaction temperature is 0~60 DEG C, then reacts aggravation higher than this temperature range, by-product increases；It is less than
Then the reaction time extends or does not react this temperature range.Reaction time is 0.2~2 hour, then reacted less than 0.2 hour and does not fill
Point.
The present invention has the beneficial effect that：
1, the present invention is to be drawn pyrrole ring under the action of catalyst through intermolecular condensation with triazolylamide ketone derivatives
Enter triazole class compounds, obtained triazole pyrrolidones series bactericidal agent, bacteriostatic activity is higher, 503nhibiting concentration (IC50) relatively low,
Fungicide is suitable as to apply under the conditions of various varying environments；
2, a kind of novel triazole pyrrolidones series bactericidal agent different from traditional commerce fungicide of present invention synthesis, provides
A kind of manufacturing cost low, easy to operate and high reaction efficiency new synthetic method.
3, the present invention has synthesized a kind of triazole pyrrolidones series bactericidal agent, and such compound is inhibiting rice blast fungus, finger-like green
There are wide research and application in terms of the mushrooms such as mould, penicillium italicum, Rhizoctonia solani.
Specific implementation mode
It is further illustrated the present invention with reference to embodiment, but the scope of protection of present invention is not limited to implement
The range of example statement.
Embodiment 1
A kind of method of synthesis 1- (4- bromophenyls) -4- phenyl -3- (1H-1,2,4- triazoles) -1H- pyrroles -2 (5H) ketone,
Including following experimental procedure：
Weigh N- (4- bromophenyls)-N- (2- methylbenzyls) -2- (1H-1,2,4- triazoles) acetamide 1 (0.80g, 2mmol)
It is added to 10mL second alcohol and waters (V with potassium carbonate (0.42g, 3mmol)Ethyl alcohol：VWater=1:1) in the mixed solvent, the electromagnetism at 30 DEG C
, there are a large amount of solids in stirring in system after 1 hour, TLC monitorings filter, are drying to obtain triazole pyrrolidones 2 after completion of the reaction：
Yield：87%
Embodiment 2
A kind of synthesis 4- (4- chlorphenyls) -1- (4- fluorophenyls) -3- (1H-1,2,4- triazoles) -1H- pyrroles -2 (5H) ketone
Method, including following experimental procedure：
Weigh N- (2- (4- chlorphenyls) -2- oxoethyls)-N- (4- fluorophenyls) -2- (1H-1,2,4- triazoles) acetamide 1
(0.75g, 2mmol) and potassium carbonate (0.42g, 3mmol) are added to 10mL second alcohol and waters (VEthyl alcohol：VWater=1:1) mixed solvent
In, there are a large amount of solids in the electromagnetic agitation at 40 DEG C in system after 1 hour, TLC monitorings are filtered, are drying to obtain after completion of the reaction
Triazole pyrrolidones 2：
Yield：83%
Embodiment 3
A kind of synthesis 4- (4- chlorphenyls) -1- (p-methylphenyl) -3- (1H-1,2,4- triazoles) -1H- pyrroles -2 (5H) ketone
Method, including following experimental procedure：
Weigh N- (2- (4- chlorphenyls) -2- oxoethyls)-N- (p-methylphenyl) -2- (1H-1,2,4- triazoles) acetamide 1
(0.74g, 2mmol) and potassium carbonate (0.42g, 3mmol) are added to 10mL second alcohol and waters (VEthyl alcohol：VWater=1:1) mixed solvent
In, there are a large amount of solids in the electromagnetic agitation at 40 DEG C in system after 2 hours, TLC monitorings are filtered, are drying to obtain after completion of the reaction
Triazole pyrrolidones 2：
Yield：79%
Embodiment 4
A kind of synthesis 4- (4- fluorophenyls) -1- (p-methylphenyl) -3- (1H-1,2,4- triazoles) -1H- pyrroles -2 (5H) ketone
Method, including following experimental procedure：
Weigh N- (2- (4- fluorophenyls) -2- oxoethyls)-N- (p-methylphenyl) -2- (1H-1,2,4- triazoles) acetamide 1
(0.70g, 2mmol) and potassium carbonate (0.42g, 3mmol) are added to 10mL second alcohol and waters (VEthyl alcohol：VWater=1:1) mixed solvent
In, there are a large amount of solids in the electromagnetic agitation at 40 DEG C in system after 2 hours, TLC monitorings are filtered, are drying to obtain after completion of the reaction
Triazole pyrrolidones 2：
Yield：76%
Embodiment 5
A kind of synthesis 1- (4- chlorphenyls) -4- (4- fluorophenyls) -3- (1H-1,2,4- triazoles) -1H- pyrroles -2 (5H) ketone
Method, including following experimental procedure：
Weigh N- (4- chlorphenyls)-N- (2- (4- fluorophenyls) -2- oxoethyls) -2- (1H-1,2,4- triazoles) acetamide 1
(0.75g, 2mmol) and potassium carbonate (0.42g, 3mmol) are added to 10mL second alcohol and waters (VEthyl alcohol：VWater=1:1) mixed solvent
In, there are a large amount of solids in the electromagnetic agitation at 30 DEG C in system after 0.5 hour, TLC monitorings filter after completion of the reaction, drying is
Obtain triazole pyrrolidones 2：
Yield：71%
Embodiment 6
A kind of synthesis 4- (4- chlorphenyls) -3- (1H-1,2,4- triazoles) -1- (4- (trifluoromethyl) phenyl) -1H- pyrroles -2
The method of (5H) ketone, including following experimental procedure：
Weigh N- (4- chlorphenyls)-N- (2- (4- fluorophenyls) -2- oxoethyls) -2- (1H-1,2,4- triazoles) acetamide 1
(0.75g, 2mmol) and potassium carbonate (0.42g, 3mmol) are added to 10mL second alcohol and waters (VEthyl alcohol：VWater=1:1) mixed solvent
In, there are a large amount of solids in the electromagnetic agitation at 30 DEG C in system after 1 hour, TLC monitorings are filtered, are drying to obtain after completion of the reaction
Triazole pyrrolidones 2：
Yield：77%
Embodiment 7
A kind of method of synthesis 1- (4- fluorophenyls) -4- phenyl -3- (1H-1,2,4- triazoles) -1H- pyrroles -2 (5H) ketone,
Including following experimental procedure：
Weigh N- (4- fluorophenyls)-N- (2- methylbenzyls) -2- (1H-1,2,4- triazoles) acetamide 1 (0.68g, 2mmol)
It is added to 10mL second alcohol and waters (V with potassium carbonate (0.42g, 3mmol)Ethyl alcohol：VWater=1:1) in the mixed solvent, the electromagnetism at 50 DEG C
, there are a large amount of solids in stirring in system after 1.5 hours, TLC monitorings filter, are drying to obtain triazole pyrrolidones after completion of the reaction
2：
Yield：75%
The above embodiments are only the preferred technical solution of the present invention, and are not construed as the limitation for the present invention, this Shen
Please in embodiment and embodiment in feature in the absence of conflict, mutually can arbitrarily combine.The protection model of the present invention
Enclose the equivalent replacement side of technical characteristic in the technical solution that should be recorded with claim, including the technical solution of claim record
Case is protection domain.Equivalent replacement i.e. within this range is improved, also within protection scope of the present invention.
Compound pop property：
2a:1-(4-bromophenyl)-4-phenyl-3-(1H-1,2,4-triazol-1-yl)-1H-pyrrol-2
(5H)-one
White solid,mp 213-214℃；1H NMR(DMSO,600MHz)δ(ppm)8.89(s,1H,Ar-H),
8.33 (s, 1H, Ar-H), 7.90 (d, J=7.2Hz, 2H, Ar-H), 7.67 (d, J=7.2Hz, 2H, Ar-H), 7.55-7.32
(m,5H,Ar-H),5.29(s,2H,CH2)；13C NMR(DMSO,150MHz)δ(ppm)164.3,152.5,146.2,145.9,
138.0,131.9,131.1,129.2,128.9,127.8,125.4,120.5,116.3,50.8；MS(EI,70eV):m/z
(%)=380 (1) [M+],289(18),211(14),105(100).Anal.Calcd for C18H13BrN4O:C,56.71；H,
3.44；N,14.70.Found:C,56.59；H,3.61；N,14.47.
2b:4-(4-chlorophenyl)-1-(4-fluorophenyl)-3-(1H-1,2,4-triazol-1-yl)-
1H-pyrrol-2(5H)-one
White solid,mp 197-198℃；1H NMR(DMSO,600 MHz)δ(ppm)8.91(s,1H,Ar-H),
8.33 (s, 1H, Ar-H), 7.92 (s, 2H, Ar-H), 7.56 (d, J=7.8 Hz, 2H, Ar-H), 7.42 (d, J=7.8 Hz,
2H, Ar-H), 7.33 (t, J=7.8 Hz, 2H, Ar-H), 5.27 (s, 2H, CH2)；M/z (%)=354 (100) [M+],298
(10),257(8),207(19),160(20),122(25),69(31).Anal.Calcd for C18H12ClFN4O:C,60.94；
H,3.41；N,15.79.Found:C,60.71；H,3.62；N,15,53.
2c:4-(4-chlorophenyl)-1-(p-tolyl)-3-(1H-1,2,4-triazol-1-yl)-1H-
pyrrol-2(5H)-one
Yellow solid,mp 215-216℃；1H NMR(DMSO,600 MHz)δ(ppm)8.91(s,1H,Ar-H),
8.32 (s, 1H, Ar-H), 7.77 (d, J=8.4 Hz, 2H, Ar-H), 7.55 (d, J=9.0 Hz, 2H, Ar-H), 7.43 (d, J
=9.0 Hz, 2H, Ar-H), 7.27 (d, J=8.4 Hz, 2H, Ar-H), 5.23 (s, 2H, CH2),2.32(s,3H,CH3)；MS
(EI,70 eV):M/z (%)=350 (100) [M+],321(13),294(19),268(6),228(8),157(11),118
(23).Anal.Calcd for C19H15ClN4O:C,65.05；H,4.31；N,15.97.Found:C,64,88；H,4.37；N,
15.72.
2d:4-(4-fluorophenyl)-1-(p-tolyl)-3-(1H-1,2,4-triazol-1-yl)-1H-
pyrrol-2(5H)-one
Light yellow solid,mp 176-177℃；1H NMR(DMSO,600 MHz)δ(ppm)8.90(s,1H,
), Ar-H 8.32 (s, 1H, Ar-H), 7.77 (d, J=8.4 Hz, 2H, Ar-H), 7.52-7.43 (m, 2H, Ar-H), 7.33 (t, J
=9.0 Hz, 2H, Ar-H), 7.26 (d, J=8.4 Hz, 2H, Ar-H), 5.23 (s, 2H, CH2),2.31(s,3H,CH3)；13C
NMR(DMSO,150MHz)δ(ppm)163.9,152.5,145.9,144.2,136.2,133.6,130.5,130.4,129.5,
126.0,125.4,118.7,116.1,116.0,51.0,20.4；MS(EI,70 eV):M/z (%)=334 (100) [M+],
305(12),278(18),237(6),212(7),118(15),91(12).Anal.Calcd for C19H15FN4O:C,68.25；
H,4.52；N,16.76.Found:C,68.09；H,4,59；N,16.71.
2e:1-(4-chlorophenyl)-4-(4-fluorophenyl)-3-(1H-1,2,4-triazol-1-yl)-
1H-pyrrol-2(5H)-one
White solid,mp 182-182℃；1H NMR(DMSO,600 MHz)δ(ppm)8.91(s,1H,Ar-H),
8.32 (s, 1H, Ar-H), 7.91 (d, J=8.4 Hz, 2H, Ar-H), 7.57 (d, J=8.4 Hz, 2H, Ar-H), 7.43 (d, J
=8.4 Hz, 2H, Ar-H), 7.28 (t, J=8.4 Hz, 2H, Ar-H), 4.26 (s, 2H, CH2)；13C NMR(DMSO,150
MHz)δ(ppm)164.0,152.6,145.6,144.3,140.5,137.7,129.1,129.0,127.4,126.7,126.8,
126.2,124.5,118.0,51.1；MS(EI,70 eV):M/z (%)=354 (100) [M+],325(3),298(12),232
(6),325(3),177(6),138(9),120(11),111(16).Anal.Calcd for C18H12ClFN4O:C,60.94；H,
3.41；N,15.79.Found:C,60.81；H,3.47；N,15.55.
2f:4-(4-chlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-1-(4-
(trifluoromethyl)phenyl)-1H-pyrrol-2(5H)-one
Light yellow solid,mp 217-219℃；1H NMR(CDCl3,600 MHz)δ(ppm)8.83(s,1H,
), Ar-H 8.12 (s, 1H, Ar-H), 7.94 (d, J=8.4 Hz, 2H, Ar-H), 7.70 (d, J=8.4 Hz, 2H, Ar-H),
7.42 (d, J=8.4 Hz, 2H, Ar-H), 7.35 (d, J=8.4 Hz, 2H, Ar-H), 4.88 (s, 2H, CH2)；13C NMR
(CDCl3,150 MHz)δ(ppm)164.0,152.5,144.6,144.5,141.0,140.6,137.5,129.3,129.2,
127.6,126.9,126.6,126.1,124.7,118.2,51.1；MS(EI,70 eV):M/z (%)=404 (100) [M+],
375(6),348(14),282(20),237(20),185(26),145(23).Anal.Calcd for C19H12ClF3N4O:C,
56.38；H,2.99；N,13.84.Found:C,56.22；H,3.05；N,13.67.
2g:1-(4-fluorophenyl)-4-phenyl-3-(1H-1,2,4-triazol-1-yl)-1H-pyrrol-2
(5H)-one
White solid,mp 188-189℃；1H NMR(CDCl3,600 MHz)δ(ppm)8.74(s,1H,Ar-H),
8.11 (s, 1H, Ar-H), 7.73 (s, 2H, Ar-H), 7.51-7.30 (s, 5H, Ar-H), 7.12 (t, J=7.8 Hz, 2H, Ar-
H),4.83(s,2H,CH2)；13C NMR(CDCl3,150 MHz)δ(ppm)163.9,160.5,158.9,152.4,144.5,
142.2,134.3,131.0,129.2,128.9,127.7,125.8,120.8,120.7,116.1,116.0,51.6；MS(EI,
70 eV):M/z (%)=320 (100) [M+],291(16),264(17),237(10),198(14),159(6),122(18)
.Anal.Calcd for C18H13FN4O:C,67.49；H,4.09；N,17.49.Found:C,67.27；H,4.24；N,17.20.
The biological activity test of target compound triazole pyrrolidones 2
Equipment and material：
Desk-top high-pressure high-temperature steam sterilization case (YXQ.DY types), the electronic balance (Sartorius of sensibility reciprocal a ten thousandth
BT25S), aseptic operating platform (will is sincere, ZHJH-C1109B), transfer needle, glass bar, graduated scale, lighter, sealed membrane, triangular flask
(75mL), graduated cylinder (20mL), microsyringe (100 μ L, 200 μ L, 500 μ L, 1000 μ L), culture dish (diameter 6cm), mould training
Support case (MJX-250 types), crocus cloth, alcolhol burner, diameter 5mm card punch.
PDA powder (Qingdao Haiyang chemical industry), distilled water, DMSO, Tween-80, gibberella saubinetii
(Gibberellasaubinetii), rice blast fungus (Magnaporthegrisea), penicillium digitatum (Penicillium
Digitatum), penicillium italicum (Penicillium italicum), Rhizoctonia solani (Rhizoctonia solani).
Experimental method (using toxic medium method is contained)
The preparation of PDA culture medium
PDA powder 46g are weighed, distilled water 1000mL is added, shakes up and is configured to solution, bottleneck is covered with cotton gauze.This is trained
Foster base is put into high-pressure sterilizing pot to be sterilized 0.5h using wet heating at 125 DEG C.
The preparation (50mg/L) of sample
2~3mg samples to be tested are weighed with assay balance to be put in the sample cell sterilized, and a few drop DMSO are added and dissolve the sample
Product are added appropriate distilled water and a drop Tween-80, are configured to the solution of uniform a concentration of 1000mg/L, take 1000 μ of this solution
L is quickly adding into (40~50 DEG C) culture medium of 9.0mL heat, shakes up the training for being configured to a concentration of 100mg/L of sample to be tested
Base is supported, ultraviolet-sterilization 15min in aseptic operating platform is lain in a horizontal plane in.
Antibacterial Activity
Strain agar block is taken with diameter 5mm card punch, inoculation will contain the PDA culture medium of candidate drug to mycelia down
On, it is placed in the center of round culture medium, cutting not slide strain agar block, in order to avoid pollution culture medium.Each sample to be tested connects
Kind three is to blank photo, with the commodity chemical drug containing same concentrations with the culture medium without drug but containing same concentrations DMSO
Object olefin conversion, triazolone as a contrast, are placed on after being cultivated 3~5 days at 25 DEG C in biochemical cultivation case, are measured on culture medium
Bacterium colony diameter.Sample to be tested is observed to bacterium by the comparison with above-mentioned blank control group and commercial pharmaceutical control group
The influence of silk growth calculates sample to be tested at 100mg/L to the inhibiting rate of bacterium colony growth.
Inhibiting rate (%)=[(blank control colony diameter-sample to be tested colony diameter)/(blank colony diameter-punching
Device diameter)] × 100%
The bacteriostatic activity test result of target compound triazole pyrrolidones 2
Table 1：The bacteriostatic activity test result of compound 2
Note：Compound concentration is 100mg/L；Data are the average value repeated three times.
From in above-mentioned table 1 it will be seen that the series compound triazole pyrrolidones 2 at 100mg/L to Italy
Penicillium notatum, penicillium digitatum, Rhizoctonia solani and rice blast fungus show certain inhibitory activity, the antibacterial work of individual compound
Property has reached higher level, if compound 2b has reached 98% to the bacteriostasis rate of penicillium digitatum, to the antibacterial of Rhizoctonia solani
Rate has also reached 94%.
Claims (8)
1. a kind of triazole pyrrolidones series bactericidal agent, which is characterized in that the chemical structural formula of the fungicide is：
Wherein, substituent R1And R2For any one in phenyl, p-bromophenyl, rubigan, p-fluorophenyl, p-methylphenyl.
2. the method for synthesis triazole pyrrolidones series bactericidal agent described in claim 1, which is characterized in that synthesis path is as follows：
Specifically include following steps：
(1) mixed solvent is prepared in reaction bulb, mixed solvent is mixed in a certain ratio by ethyl alcohol and water；
(2) compound 1 is added in the in the mixed solvent into the step (1), and reaction system is placed at 0~60 DEG C by potassium carbonate
It is stirred to react 0.2~2 hour, until there are a large amount of solids in system；
The compound 1 is triazole acyl ammonia ketone；
(3) the reaction solution TLC monitorings of the step (2) is taken to filter, residue is through drying to obtain compound after completion of the reaction
2, you can complete the synthesis of triazole pyrrolidones series bactericidal agent.
3. method according to claim 2, it is characterised in that：The step (1) prepares the ethyl alcohol that mixed solvent uses and water
Volume ratio is 1:1.
4. method according to claim 2, it is characterised in that：Step (2) compound 1 and the potassium carbonate mass ratio that feeds intake are 2:
3。
5. method according to claim 2, it is characterised in that：Step (2) reaction temperature is 0~60 DEG C, and the reaction time is
0.2~2 hour.
6. the triazole pyrrolidones series bactericidal agent that claim 2-5 any one is prepared is inhibiting rice blast fungus, Penicillium digitatum
Bacterium, penicillium italicum, the application on Rhizoctonia solani.
7. the application described in claim 6, which is characterized in that and 4- (4- chlorphenyls) -1- (4- fluorophenyls) -3- (1H-1,2,4- tri-
Azoles) application of (5H) ketone of -1H- pyrroles -2 on inhibiting Penicillium notatum, structural formula is：
8. the application described in claim 6, which is characterized in that 4- (4- chlorphenyls) -3- (1H-1,2,4- triazoles) -1- (4- (three
Methyl fluoride) phenyl) application of (5H) ketone of -1H- pyrroles -2 on inhibiting Penicillium notatum, structural formula is：
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| CN109400588B (en) * | 2018-12-07 | 2020-09-25 | 湖北文理学院 | Fluorine-containing triazole quinoxaline bactericide, preparation method and application thereof |
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| CN86106264A (en) * | 1985-09-19 | 1987-06-03 | 尤尼罗亚尔化学公司 | Substituted oxathiolanes |
| CN1030232A (en) * | 1987-06-30 | 1989-01-11 | 吴羽化学工业株式会社 | Novel pyrrole derivative and production method thereof and contain the agricultural of this pyrrole derivative and the chemical composition that gardening is used |
| CN1138862A (en) * | 1994-01-24 | 1996-12-25 | 詹森药业有限公司 | Watersoluble azole antifungals |
| CN102510721A (en) * | 2009-07-16 | 2012-06-20 | 拜尔农作物科学股份公司 | Synergistic active substance combinations containing phenyl triazoles |
| CN105017232A (en) * | 2015-07-29 | 2015-11-04 | 江苏七洲绿色化工股份有限公司 | Synthesis method of triazole bactericide |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN86106264A (en) * | 1985-09-19 | 1987-06-03 | 尤尼罗亚尔化学公司 | Substituted oxathiolanes |
| CN1030232A (en) * | 1987-06-30 | 1989-01-11 | 吴羽化学工业株式会社 | Novel pyrrole derivative and production method thereof and contain the agricultural of this pyrrole derivative and the chemical composition that gardening is used |
| CN1138862A (en) * | 1994-01-24 | 1996-12-25 | 詹森药业有限公司 | Watersoluble azole antifungals |
| CN102510721A (en) * | 2009-07-16 | 2012-06-20 | 拜尔农作物科学股份公司 | Synergistic active substance combinations containing phenyl triazoles |
| CN105017232A (en) * | 2015-07-29 | 2015-11-04 | 江苏七洲绿色化工股份有限公司 | Synthesis method of triazole bactericide |
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