CN109053681A - The purposes of sulfonyl -1,2,3- triazole class compounds and its wettable powder in prevention and treatment wheat rust - Google Patents
The purposes of sulfonyl -1,2,3- triazole class compounds and its wettable powder in prevention and treatment wheat rust Download PDFInfo
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- CN109053681A CN109053681A CN201811151022.2A CN201811151022A CN109053681A CN 109053681 A CN109053681 A CN 109053681A CN 201811151022 A CN201811151022 A CN 201811151022A CN 109053681 A CN109053681 A CN 109053681A
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- amido
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Abstract
The invention discloses sulfonyl shown in formula I -1,2,3-triazoles class compound or its pharmaceutically acceptable salt,
Description
Technical field
The present invention relates to disinfectant use in agriculture fields, and in particular to sulfonyl -1,2,3-triazoles class compound and its wettable
Purposes of the pulvis in prevention and treatment wheat rust.
Background technique
Wheat rust is called jaundice, is that can be divided into stripe rust, leaf rust and stem rust by fungus-caused a kind of disease
3 kinds, be a kind of disease that occurring area is wide on China's wheat, harm is most heavy.Three kinds of rest fungus are all with the uredospore generation in China
It is infected on the wheat crops based on wheat by generation and completes anniversary circulation, be typical long-range aeroborne disease.Wheat is felt
Wound can be formed on planting pearl after dye, the loss of moisture and nutrient is caused, destroy chlorophyll, restrict the development of wheat with
Growth.Between wheat rust popular year, wheat be averaged underproduction 10%-20%, and the serious time understands the underproduction 30% or so, or even can make
At some fields, No kernels or seeds are gathered, as in a year of scarcity.
Control rust often uses chemical agent with triazolone (triadimefon), olefin conversion (fast Poly), propiconazole (enemy's power at present
It is de-) etc. based on triazole bactericidal agents.Triazole bactericidal agent antibacterial activity is good, but can inhibit the biosynthesis of plant gibberellin.It is red
Mycin is the Plant Hormone for promoting cell growth, and physiological effect most outstanding is elongation and the induction long day plant for promoting stem
Bolting is bloomed under the conditions of short day.Gibberellin, which is suppressed, will affect plant strain growth and development, influence the yield of wheat.
Research of the sulfonyl -1,2,3- triazole class compounds that the present invention mentions in terms of preventing and treating wheat rust there is no at present
Report, for wheat leaf rust prevention and treatment, do not influence wheat germination and emergence provides the new research direction of one kind.
Summary of the invention
The present invention provides a kind of sulfonyl -1,2,3-triazoles class compound, structure is shown in formula I:
Wherein Ar is selected from piperazinyl, anilino-, 4- toluidine, 4- fluorobenzene
Amido, 4- chloroanilino, 4- bromobenzene amido, 4- cyano-aniline base, 4- trifluoromethylbenzene amido, 4- methoxybenzene amido, 2- first
Base anilino-, 2- fluoroanilino, 2- chloroanilino, 2- bromobenzene amido, 2- cyano-aniline base, 2- trifluoromethylbenzene amido, 2- first
Oxygroup anilino-, 3- toluidine, 3- fluoroanilino, 3- chloroanilino, 3- bromobenzene amido, 3- cyano-aniline base, 3- trifluoro
Toluidine, 3- methoxybenzene amido, naphthalidine base, quinoline -5- amido, 1- piperidyl, 1- pyrrolidinyl.
Further, the sulfonyl -1,2,3-triazoles class Formula I pharmaceutically acceptable salt.
Further, the sulfonyl -1,2,3-triazoles class Formula I is selected from compound 1-27, and structure is as follows:
The present invention also provides the preparations of the sulfonyl -1,2,3- triazole class compounds or its pharmaceutically acceptable salt
Method, the specific steps are as follows: 3- (3- methoxyphenyl) propiolic acid (Formula II) and 4- group-4 ethyl formate diazonium tetrafluoro phenyl boric acid (formula
III) in thiophene -2-carboxylic acid copper and DABCO (SO2)2It acts on lower low-temp reaction (step 1) and obtains intermediate 1；In obtained
Mesosome 1 reacts (step 2) with 4- nitrine pyridine under the catalytic action of pyrrolidines and obtains intermediate 2；Obtained intermediate 2
Hydrolysis (step 3) occurs under alkaline condition and obtains intermediate 3；Intermediate 3 and amine compound are in condensation reagent and two
Under diisopropylethylamine effect (step 4), Formulas I structured product is finally obtained, reaction process is as follows:
Further, condensation reagent used by preparation formula I structured product (step 4) be HATU, HBTU, HCTU,
TATU、TBTU、TCTU、TPTU、TSTU、HOAT、HOBT、DCI、DIEA、PyAOP、PyBOP、DCC、DMAP、DBU、CDI、
One of HOOBt, Cl-HOBT, EDC.
The composition of sulfonyl -1,2,3- triazole class compounds Formulas I wettable powder prescription of the present invention are as follows: sulfonyl -
1,2,3-triazoles class compound or 20-80 parts of its pharmaceutically acceptable salt, 20-80 parts of carrier, 1-5 parts of wetting agent and dispersing agent
1-20 parts.The auxiliary agent for wherein playing carrier function is diatomite, white carbon black, bentonite, precipitated calcium carbonate, attapulgite, kaolin
One or more of.The auxiliary agent for wherein playing wetting agent is lauryl sodium sulfate, neopelex, pulls open
Powder, wetting agent T, fatty alcohol polyoxyethylene ether JFC, alkyl phenol polyoxyethylene ether NP, pancreas add source T, octylphosphonic acid salt, pine tar soap,
One or more of octylphenol polyethylene oxyethylene group ether sulfate, rope uncle.The auxiliary agent for wherein playing dispersing agent is NNO, wooden
Plain sodium sulfonate, ORZAN-P, DAXAD, calgon, starch, gelatin, Arabic gum, lecithin, carboxymethyl cellulose, poly- second
One or more of enol, polyvinylpyrrolidone, Sodium Polyacrylate, polyethylene glycol.Other carriers, other tools also may be selected
The wetting agent and other dispersing agents with peptizaiton for having wetting action are applied in the present invention.
Preparation method of the invention includes the steps that following sequence:
(1) raw material is weighed by the proportion speed of wettable powder；
(2) it by sulfonyl -1,2,3-triazoles class compound, dispersing agent investment mixer, is uniformly mixed；
(3) wetting agent and carrier are sequentially added, it is secondary to be uniformly mixed；
(4) mixture is transferred to airslide disintegrating mill to crush, controls the fineness of solid material between 580-620 mesh, obtains
The wettable powder of sulfonyl -1,2,3- triazole class compounds.
The influence test that the present invention also provides the compounds to the indoor harmacological effect of wheat rust, to wheat germination situation
And wettable powder suspensibility and wetting time measure, find compound of the present invention can work the short time significantly fight it is small
Wheat rust, and on the germination of wheat and emergence without influence；The wettable powder suspensibility is high, wetting time is short.
Specific embodiment
Embodiment 1: the synthesis of intermediate 1
Thiophene -2-carboxylic acid copper (0.02mmoL), 3- (3- methoxyphenyl) are sequentially added under condition of nitrogen gas, in round-bottomed flask
Propiolic acid (0.2mmoL), 4- group-4 ethyl formate diazonium tetrafluoro phenyl boric acid (0.24mmoL), DABCO (SO2)2(0.4mmoL), water
(0.2mmoL) and 1,2- dichloroethanes (1.5mL).Saturated sodium bicarbonate, methylene chloride extraction is added in 0 DEG C of stirring 2h of reaction solution.
It being filtered after organic phase anhydrous sodium sulfate drying after merging, filtrate concentrated by rotary evaporation, residue column chromatographs (PE/EA=4/1) purifying,
Obtain intermediate 1, yield 66%.1H-NMR(400MHz,CDCl3) δ 7.76 (d, J=8.0Hz, 2H), 7.50 (d, J=
7.6Hz, 1H), 7.44-7.27 (m, 4H), 7.14 (d, J=8.1Hz, 1H), 4.79 (s, 2H), 4.43 (q, J=7.1Hz, 2H),
3.81 (s, 3H), 1.42 (t, J=7.1Hz, 3H) .Mass (ESI) m/z M+calcd 363.08；found 363.09.
Embodiment 2: the synthesis of intermediate 2
Intermediate 1 (0.3mmoL), 4- nitrine pyridine (0.33mmoL) and DMSO (1mL) are added in round-bottomed flask, stirs molten
Pyrrolidines (0.5mol%) is added after solution, mixture is stirred at room temperature for 24 hours.Saturated salt solution and ethyl acetate is added in reaction solution, point
Liquid.Anhydrous sodium sulfate dries, filters after organic phase saturated common salt is washed 3 times, filtrate concentrated by rotary evaporation, and residue column chromatographs (PE/EA
=1/1) it purifies to get intermediate 2, yield 48% is arrived.1H-NMR(400MHz,DMSO-d6)δ8.60-8.52(m,2H),7.77
(d, J=8.0Hz, 2H), 7.71-7.70 (m, 2H), 7.52 (d, J=7.6Hz, 1H), 7.45-7.28 (m, 4H), 7.15 (d, J
=8.1Hz, 1H), 4.44 (q, J=7.1Hz, 2H), 3.82 (s, 3H), 1.44 (t, J=7.1Hz, 3H) .Mass (ESI) m/z M+calcd 465.12；found 465.33.
Embodiment 3: the synthesis of intermediate 3
The mixed liquor of intermediate 2 (0.1mmoL) and ethyl alcohol/tetrahydrofuran (4/1) are added in round-bottomed flask, stirring is all molten
The sodium hydroxide solution (2mL) of 1M is added dropwise under ice bath by Xie Hou.It is added dropwise, reaction solution is slowly increased to that 3h is stirred at room temperature.It has reacted
The HCl solution of 1M is added dropwise after complete under ice bath to pH 6-7, ethyl acetate extracts.After organic phase anhydrous sodium sulfate drying after merging
Filtering, filtrate concentrated by rotary evaporation to get arrive intermediate 3, yield 85%.1H-NMR(400MHz,DMSO-d6)δ8.59-8.51(m,
2H), 7.76 (d, J=8.0Hz, 2H), 7.70-7.68 (m, 2H), 7.50 (d, J=7.6Hz, 1H), 7.44-7.28 (m, 4H),
7.13 (d, J=8.1Hz, 1H), 3.81 (s, 3H) .Mass (ESI) m/z [M+Na]+calcd 459.08；found 459.12.
Embodiment 4: the synthesis of compound 1
Intermediate 3 (1mmoL), HATU (1mmoL), diisopropyl ethyl amine (2.5mmoL) are sequentially added in round-bottomed flask
And DMF, N- tert-butoxycarbonyl-piperazine (1mmoL) is added after 30min is stirred at room temperature.Saturation is added after being stirred overnight at room temperature in reaction solution
Sodium bicarbonate solution, ethyl acetate extraction.It is filtered after organic phase anhydrous sodium sulfate drying after merging, filtrate concentrated by rotary evaporation is residual
Excess column chromatographs (PE/EA=1/2) purifying, obtains yellow solid.
Yellow solid obtained in the previous step is dissolved in after 1,4- dioxane, hydrogen chloride/1,4- dioxy six is added dropwise under ice bath
Ring solution.It finishes, 6h, reaction solution saturated sodium bicarbonate solution tune pH 7.0, ethyl acetate extraction, after merging is stirred at room temperature
It is filtered after organic phase anhydrous sodium sulfate is dry, filtrate concentrated by rotary evaporation obtains compound 1, yield 55%.1H-NMR(400MHz,
DMSO-d6) δ 8.59-8.55 (m, 2H), 7.78 (d, J=8.0Hz, 2H), 7.71-7.68 (m, 2H), 7.51 (d, J=7.6Hz,
1H), 7.44-7.39 (m, 4H), 7.14 (d, J=8.1Hz, 1H), 4.02-4.09 (m, 4H), 3.83 (s, 3H), 3.74-3.81
(m,4H).Mass(ESI)m/z M+calcd 505.16；found 505.21.
Embodiment 5: 60% wettable powder of compound 1
One, prescription:
Compound 160g, neopelex 1g, dispersing agent NNO 5g, diatomite 34g.
Two, step:
1, raw material is weighed by prescription proportion speed；
2, it by compound 1, dispersing agent NNO investment mixer, is uniformly mixed；
3, neopelex and diatomite are sequentially added, it is secondary to be uniformly mixed；
4, mixture is transferred to airslide disintegrating mill to crush, controls the fineness of solid material between 580-620 mesh, is changed
Close 60% wettable powder of object 1.
Embodiment 6: 40% wettable powder of compound 1
One, prescription:
Compound 140g, neopelex 1g, dispersing agent NNO 5g, diatomite 54g.
Two, step:
1, raw material is weighed by prescription proportion speed；
2, it by compound 1, dispersing agent NNO investment mixer, is uniformly mixed；
3, neopelex and diatomite are sequentially added, it is secondary to be uniformly mixed；
4, mixture is transferred to airslide disintegrating mill to crush, controls the fineness of solid material between 580-620 mesh, is changed
Close 40% wettable powder of object 1.
Embodiment 7: 60% wettable powder of compound 1
One, prescription:
Compound 160g, pull open powder 2g, sodium lignin sulfonate 10g, diatomite 28g.
Two, step:
1, raw material is weighed by prescription proportion speed；
2, it by compound 1, sodium lignin sulfonate investment mixer, is uniformly mixed；
3, pull open powder and diatomite are sequentially added, it is secondary to be uniformly mixed；
4, mixture is transferred to airslide disintegrating mill to crush, controls the fineness of solid material between 580-620 mesh, is changed
Close 60% wettable powder of object 1.
Embodiment 8: 40% wettable powder of compound 1
One, prescription:
Compound 140g, pull open powder 2g, sodium lignin sulfonate 10g, diatomite 48g.
Two, step:
1, raw material is weighed by prescription proportion speed；
2, it by compound 1, sodium lignin sulfonate investment mixer, is uniformly mixed；
3, pull open powder and diatomite are sequentially added, it is secondary to be uniformly mixed；
4, mixture is transferred to airslide disintegrating mill to crush, controls the fineness of solid material between 580-620 mesh, is changed
Close 40% wettable powder of object 1.
The preparation of 1 seed coat agent of embodiment 9:2% compound
One, prescription:
Compound 12g, polyvinylpyrrolidone 4g, styrene polyoxyethylene ether ammonium sulfate 4g, enuatrol 3g, dodecyl
Benzene sulfonic acid sodium salt 6g, glycerine 0.3g, xanthan gum 0.8g, silicone oil 1g, basic rhodamine 0.8g, water complement to 100g.
Two, step:
First by polyvinylpyrrolidone, styrene polyoxyethylene ether ammonium sulfate, enuatrol, neopelex, third
Triol, xanthan gum, silicone oil and water are uniformly mixed through high speed shear, and are added compound 1 and are ground 2h into sand mill, make partial size
Less than 5 μm, it is eventually adding basic rhodamine, is uniformly mixed, that is, 2% seed coat agent of compound 1 is made.
The preparation of embodiment 10:2% Triadimenol seed coat agent
One, prescription:
Triadimenol 2g, polyvinylpyrrolidone 4g, styrene polyoxyethylene ether ammonium sulfate 4g, enuatrol 3g, dodecyl
Benzene sulfonic acid sodium salt 6g, glycerine 0.3g, xanthan gum 0.8g, silicone oil 1g, alkaline basic rhodamine 0.8g, water complement to 100g.
Two, step:
First by polyvinylpyrrolidone, styrene polyoxyethylene ether ammonium sulfate, enuatrol, neopelex, third
Triol, xanthan gum, silicone oil and water are uniformly mixed through high speed shear, and are added Triadimenol and are ground 2h into sand mill, make partial size
Less than 5 μm, it is eventually adding basic rhodamine, is uniformly mixed, that is, 2% seed coat agent of Triadimenol is made.
Compound 1 is replaced with into any compound of the present invention in embodiment 5-9, same agents type can be obtained
Prescription and processing step, the present invention in do not repeat them here.
Test example 1: indoor harmacological effect of the compound to wheat rust
Bacterium is connect using spray-on process, wheat leaf rust germ spore is dissolved in alcohol, after be sprayed to potting wheat seeding (2 leaf phase)
On, it is put into 8-24h in moisturizing tower.Germ is sufficiently administered after the onset, and every basin wheat seeding is a repetition, 6 repetitions of each medicine, if clearly
Water is blank control, and sun ginseng triazolone is positive control, 20 DEG C of constant temperature indoor cultures.Using T.Aestivum/
0-9 grades of stagings of P.striiformis interaction are classified by the percentage that scab on blade accounts for entire leaf area.Its
Grade scale are as follows:
0 grade: disease-free spot；
1 grade: scab accounts for 5% or less entire leaf area；
3 grades: scab accounts for the 6%-10% of entire leaf area；
5 grades: scab accounts for the 11%-25% of entire leaf area；
7 grades；Scab accounts for the 26%-50% of entire leaf area；
9 grades: scab accounts for 50% or more of entire leaf area.
Respectively at the infection conditions of 5d, 10d investigation wheat leaf rust germ after spray, disease index and correction prevention and treatment effect are calculated
Fruit.The results are shown in Table 1.
Disease index=∑ (the diseased plant numbers at different levels × disease grade value)/(investigation total strain number × superlative degree value) × 100
Opposite control efficiency (%)=(control disease index-processing disease index)/control disease index × 100
Control efficiency of 1 compound of table to wheat rust
Test result is shown, 5 days after application, treated that wheat rust disease refers to is significantly lower than for the compounds of this invention 1,7,9
Positive control drug, control efficiency are more preferable；10 days after application, the control effect of 1,7,9 pair of wheat rust of the compounds of this invention is also bright
It is aobvious to be better than positive control drug.Show the compounds of this invention can it is more shorter than positive control drug onset time, effect is more preferable.
Experimental example 2: influence of 1 seed coat agent of compound to wheat germination situation
1, test material:
Embodiment 9 (2% compound, 1 seed coat agent), embodiment 10 (2% Triadimenol seed coat agent), 411 wheat of capital.2, it tests
Method:
411 wheat of capital is taken to use 9 seed coat agent of embodiment and 10 seed coat agent of embodiment by 0.3,0.6,1.2,2.4g ai/ respectively
Kg seed treatment, not handle in the sand culture ware for being sowed at the water content through high-temperature sterilization 17% for blank control, 50, every ware,
25, every basin, 3 repetitions of every processing, is placed in incubator and cultivates.Measure germinating energy, germination percentage and emergence rate.Test result is shown in
Table 2.
Influence of the table 2 to wheat germination and emergence
Test result shows that wheat germination gesture, germination percentage and the emergence rate of Triadimenol coating are in the increase of coating dosage
Conspicuousness decline, Triadimenol are inhibited to the sprouting of seed.Difference coating dosages compounds 1 to wheat germination gesture,
Germination percentage and emergence rate are unchanged, show compound 1 to the noiseless effect of the sprouting of seed.
Test example 3: wettable powder suspensibility and wetting time measure
1, suspensibility measures:
Sample 1.25g (being accurate to 0.0002g) is weighed, according in agricultural-chemical suspension rate measuring method GB/T 14825-2006
3.1 regulations carry out, and are placed in the 200mL beaker for filling 30 ± 2 DEG C of 50mL standard hard water, are circled with hand, and about every point
Clock 120 times, 2min is carried out, which is placed into 13min in the water-bath of same temperature, then the standard with 30 ± 2 DEG C is hard
Water washes its whole in 250mL graduated cylinder, and is diluted to scale, covers plug, using graduated cylinder bottom as axle center, by graduated cylinder in 1min
It inside turns upside down 30 times.Plug is opened, in being vertically put into vibrationless water bath with thermostatic control, places 30min.With suction pipe in 10-15s
Interior 90% suspension by content removes, and not shake or stir the sediment in graduated cylinder, it is ensured that the top of suction pipe exists always
Under liquid level at several millimeters.
10% suspension remaining in graduated cylinder and sediment are all moved into 100mL beaker, are dried in 70 DEG C of baking ovens
It is micro- it is dry after it is cooling, then according to prescriptive procedure in this standard, measure the quality of compound 1, and calculate suspensibility.
Suspensibility X2(%) calculation formula: X2=(10/9) × [(m3-m4)/m3]×100
m3It materialses the quality (g) of middle effective component for configuration suspension；m4To stay in the 25mL suspension of graduated cylinder bottom
The quality (g) of effective component.
2, the measurement of wetting time:
Sample 5.0g is weighed, pours into equipped in 100mL constant temperature hard water (342ppm) mother liquor, records wetting time rapidly.
The suspensibility and wetting time of 1 wettable powder of compound are shown in Table 3.
The suspensibility and wetting time of 3 compound of table, 1 wettable powder
| Suspensibility (%) | Wetting time (s) | |
| Embodiment 5 | 95 | 50 |
| Embodiment 6 | 92 | 39 |
| Embodiment 7 | 91 | 48 |
| Embodiment 8 | 94 | 53 |
Test result shows that four kinds of wettable powder embodiments 5, embodiment 6, embodiment 7, the embodiment 8 of compound 1 are equal
With good water dispersible, can quickly be dispersed in water.
Claims (10)
1. sulfonyl -1,2,3-triazoles class compound or its pharmaceutically acceptable salt, structure are shown in formula I:
Wherein Ar be selected from piperazinyl, anilino-, 4- toluidine, 4- fluoroanilino,
4- chloroanilino, 4- bromobenzene amido, 4- cyano-aniline base, 4- trifluoromethylbenzene amido, 4- methoxybenzene amido, 2-aminotoluene
Base, 2- fluoroanilino, 2- chloroanilino, 2- bromobenzene amido, 2- cyano-aniline base, 2- trifluoromethylbenzene amido, 2- methoxybenzene
Amido, 3- toluidine, 3- fluoroanilino, 3- chloroanilino, 3- bromobenzene amido, 3- cyano-aniline base, 3- trifluoromethylbenzene
Amido, 3- methoxybenzene amido, naphthalidine base, quinoline -5- amido, 1- piperidyl, 1- pyrrolidinyl.
2. sulfonyl as described in claim 1-1,2,3-triazoles class compound or its pharmaceutically acceptable salt, specific structure
Are as follows:
3. sulfonyl -1,2,3- triazole class compounds as described in claim 1 or its pharmaceutically acceptable salt are as prevention and treatment
Application in wheat rust.
4. the preparation side of sulfonyl -1,2,3- triazole class compounds as described in claim 1 or its pharmaceutically acceptable salt
Method, it is characterized in that:
Step 1: 3- (3- methoxyphenyl) propiolic acid (Formula II) and 4- group-4 ethyl formate diazonium tetrafluoro phenyl boric acid (formula III) exist
Thiophene -2-carboxylic acid copper and DABCO (SO2)2It acts on lower low-temp reaction and obtains intermediate 1；Step 2: obtained intermediate 1 with
4- nitrine pyridine reacts under the catalytic action of pyrrolidines obtains intermediate 2；
Step 3: hydrolysis occurs under alkaline condition and obtains intermediate 3 for obtained intermediate 2；Step 4: intermediate 3
With amine compound under condensation reagent and diisopropyl ethyl amine effect, Formulas I structured product is finally obtained, reaction process is such as
Under:
5. preparation method as claimed in claim 4, it is characterized in that: condensation reagent employed in the step 4 be HATU,
HBTU、HCTU、TATU、TBTU、TCTU、TPTU、TSTU、HOAT、HOBT、DCI、DIEA、PyAOP、PyBOP、DCC、DMAP、
One of DBU, CDI, HOOBt, Cl-HOBT, EDC.
6. a kind of wettable powder, it is characterized in that: containing sulfonyl described in claim 1-1,2,3-triazoles class compound or
Active constituent, carrier, wetting agent and the dispersing agent of its pharmaceutically acceptable salt.
7. wettable powder as claimed in claim 6, it is characterized in that: the sulfonyl -1,2,3-triazoles class compound or its
The prescription proportion of pharmaceutically acceptable salt is 20-80 parts.
8. wettable powder as claimed in claim 6, it is characterized in that: the carrier be selected from diatomite, white carbon black, bentonite,
One or more of precipitated calcium carbonate, attapulgite, kaolin, the carrier prescription proportion is 20-80 parts.
9. wettable powder as claimed in claim 6, it is characterized in that: the wetting agent is selected from lauryl sodium sulfate, 12
Sodium alkyl benzene sulfonate, pull open powder, wetting agent T, fatty alcohol polyoxyethylene ether JFC, alkyl phenol polyoxyethylene ether NP, pancreas add source T, pungent
One or more of based phosphates, pine tar soap, octylphenol polyethylene oxyethylene group ether sulfate, rope uncle, the wetting agent prescription
Proportion is 1-5 parts.
10. wettable powder as claimed in claim 6, it is characterized in that: the dispersing agent be selected from NNO, sodium lignin sulfonate,
ORZAN-P, DAXAD, calgon, starch, gelatin, Arabic gum, lecithin, carboxymethyl cellulose, polyvinyl alcohol, poly- second
One or more of alkene pyrrolidone, Sodium Polyacrylate, polyethylene glycol, the dispersing agent prescription proportion is 1-20 parts.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811151022.2A CN109053681B (en) | 2018-09-29 | 2018-09-29 | The purposes of sulfonyl -1,2,3- triazole class compounds and its wettable powder in prevention and treatment wheat rust |
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| CN201811151022.2A CN109053681B (en) | 2018-09-29 | 2018-09-29 | The purposes of sulfonyl -1,2,3- triazole class compounds and its wettable powder in prevention and treatment wheat rust |
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| CN109053681A true CN109053681A (en) | 2018-12-21 |
| CN109053681B CN109053681B (en) | 2019-07-02 |
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| CN111072531A (en) * | 2019-12-16 | 2020-04-28 | 江南大学 | Synthesis method of β -ketosulfone compound |
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| CN1071924A (en) * | 1991-10-29 | 1993-05-12 | 纳幕尔杜邦公司 | The triazolecarboxamides of weeding |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072531A (en) * | 2019-12-16 | 2020-04-28 | 江南大学 | Synthesis method of β -ketosulfone compound |
| CN111072531B (en) * | 2019-12-16 | 2021-09-24 | 江南大学 | Synthesis method of beta-ketosulfone compound |
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