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triazolone
Other names: Beliton, Triamcinolone acetonide, Amiral.
Physical and chemical properties
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Molecular formula: C 14H 16ClN3O2.
Molecular weight: 293.7
CAS: 43 12 1-43-3
EINECS:256- 103-8
Chemical name: 1-(4- chlorophenoxy)-3,3-dimethyl-1-( 1H- 1, 2,4- triazole -l- yl)-α-butanone.
Triadimefon is a colorless solid with a melting point of 82-83℃ and a special flavor. Its vapor pressures are 0.02mPa(20℃) and 0.06mPa (25℃), its density is 1.22(20℃), its Kowlog P is 3. 1 1, and its solubility in water is 64 mg/. 200, isopropanol 50- 100, hexane 5- 10g/L (20℃), acid or alkali (pH 1- 13). The half-life of pH 3,6,9 (22℃) exceeds 1 year.
Three characteristics
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Triadimefon is a triazole fungicide with high efficiency, low toxicity, low residue, long duration and strong systemic property. After being absorbed by various parts of plants, it can be conducted in plants. It has the functions of preventing, eradicating and treating rust and powdery mildew. It is effective for many crop diseases such as corn leaf spot, wheat moire, wheat leaf blight, pineapple black rot, corn head smut and so on. Safe for fish and [1] birds. Harmless to bees and natural enemies. The bactericidal mechanism of triadimefon is extremely complicated, mainly inhibiting ergosterol biosynthesis, thus inhibiting or interfering with the development of adherent spores and haustorium, the growth of hyphae and the formation of spores. Triadimefon has a strong inhibitory effect on some bacteria in vivo, but it has a poor effect in vitro. The activity of mycelium is stronger than that of spore. Triadimefon can be mixed with many fungicides, insecticides and herbicides.
Four dosage forms
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5%, 15%, 25% wettable powder, 25%, 20%, 10% emulsifiable concentrate, 20% ointment, 25% colloidal suspension, 0.5%, 1%, 10% powder.
5 Scope of application
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It has special effects on rust, powdery mildew and smut, and has good control effect on smut and corn leaf spot of corn and sorghum.
6 method of use
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1, wheat head smut, rust, powdery mildew, moire and other wheat head smuts, 100 kg of seeds mixed with 30 g of active ingredients (200 g 15% wettable powder); For rust, powdery mildew and moire, 8.75g (25% EC 35) of active ingredients can be used per mu at the initial stage of the disease, and100g of active ingredients (25% EC 60) 75-100kg of water can be sprayed in severe cases.
2. In order to control the head smut of corn and sorghum, 533g of 100 kg seeds were dressed with 15% wettable powder. 100 kg of sorghum head smut seeds were treated with 266-400 g 15% wettable powder.
3. Spraying 25% wettable powder 1-2 times 5000 times solution on cucumber powdery mildew in the field and spraying 25% wettable powder 1-2 times 1000 times solution in the greenhouse. Soybean rust can be sprayed with 2000 times of 25% wettable powder 1-2 times at the initial stage of onset or reinfection.
Triadimefon, also known as triadimefon and bailitong, is the first triazole fungicide widely used. It has special effects on powdery mildew, rust and smut, so it has a good name: "Fenxiuning".
Triadimefon is widely used in China. There are many manufacturers of original drugs and preparations, and there are many kinds of preparations developed, mainly 15%, 20% EC, 8%, 10%, 12% hypertonic EC, 12% synergistic EC and 10%.
Triadimefon is applied in many ways, such as spraying stems and leaves, treating seeds, treating soil and so on.
Triadimefon is an efficient and long-lasting systemic fungicide, which has the functions of prevention, treatment, eradication and fumigation. Its mechanism is mainly to inhibit the synthesis of ergosterol, thus inhibiting the growth of mycelium and the formation of spores.
7 preventive measures
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Besides alkaline preparation and copper preparation, it can be mixed with other preparations. Seed dressing may delay the emergence of seeds by 1-2 days, but it does not affect the emergence rate and late growth. Put the medicine in a dry and ventilated place. There is no specific medicine, only symptomatic treatment.
The indications of trazodone, triadimefon mbth and syringaldehyde are suitable for treating depression and melancholia caused by various reasons, and are also effective for anxiety, insomnia and excitement. It takes effect within 1 ~ 2 weeks after taking the medicine. Dosage and usage: oral: 50mg at first, 3 times a day, and then increased as appropriate, with a maximum of 400 ~ 600 mg per day. People who are sleepy can take medicine before going to bed. The side effects of precautions are few and light, and the common ones are drowsiness, dry mouth, fatigue, constipation and blurred vision. Occasionally tachycardia, decreased or increased blood pressure, tremor, stomachache, loss of appetite, rash, weight change, etc. There are also some patients with leukopenia and menstrual disorders. Specification tablets: 50mg/ tablet, 100mg/ tablet.
Symptoms of poison poisoning: Generally, it only irritates eyes and skin.
First aid: No poisoning report. Symptomatic treatment, vomiting and gastric lavage immediately after eating.
Precautions: Use according to the prescribed dosage, otherwise the crops will be vulnerable to drug damage.
Environmental aquatic organisms: LC50(96 hours, mg/L) 13.8, trout 17.4, blue gill sunfish 1 1.
Bee: non-toxic.
Natural enemies: acute oral LD50 quail >: 4000mg/kg, LC50(8 days, meal) wild duck >: 10000, quail >; 4640
Soil and water conservation: the half-life is about 18 days (sandy loam) and about 6 days (loam), Ko
8 preparation method
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Production method:
α-bromopinene reacts with sodium chlorophenol to generate α-p-chlorophenoxy benzophenone, then with bromine to generate α-p-chlorophenoxy-α-bromopinene, and finally with 1, 2,4-triazole to generate triadimefon. The content of triadimefon powder is above 96%, and the main pesticide formulations are 20% emulsifiable concentrate and 15% wettable powder.
Method one
1, 2,4-triazole ammonium formate is prepared by introducing ammonia into formic acid and then reacting with hydrazine hydrate to obtain 1, 2,4-triazole.
Preparation of Pinone Monochloride Isoamyl alcohol was dehydrated and transposed under the catalysis of activated alumina to produce isopentene. 2- methyl-1- butene and 2- methyl -2- butene are added with hydrogen chloride to form chlorinated tertiary pentane. Then it reacts with formaldehyde in acidic solution to generate pinadone, and chlorine gas is introduced in the presence of solvent to obtain monochloropinadone.
Triadimefon was synthesized with p-chlorophenol in the presence of potassium carbonate, 1-(4- chlorophenoxy) pinanone was prepared in toluene solvent, and then 1-(4- chlorophenoxy)-1- chlorophenoxy was prepared by chlorination with sulfur chloride. Triadimefon was synthesized from 1, 2,4-triazole with a yield of 88%.
In the reaction, sodium iodide can be used as catalyst and anhydrous potassium carbonate as acid binding agent to synthesize ether ketone, then carbon tetrachloride can be used as solvent to react with thionyl chloride to obtain α-chloroether ketone with quantitative yield, and then triadimefon can be synthesized with 1, 2,4-triazole in acetone solvent with a yield of 87%.
Method 2
Stolzer et al. reported in 1977 that in acetone solvent, α, α-dichloropineone, p-chlorophenol and 1, 2,4-triazole were used as acid binding agents, and the product was refluxed 15h, and then treated with acid and alkali, with a yield of 60% ~.
The one-step method studied in China is to synthesize triadimefon by the reaction of α, α-dichloropinadone, p-chlorophenol and 1, 2,4-triazole. The method of one-step synthesis of triadimefon by phase transfer catalysis is as follows: 0.29 g (10 mmol) of p-chlorophenol, 0.9 g (13 mmol) 1 2, 4- triazole, 3.5 g (22.4 mmol) powdered anhydrous potassium carbonate, and polyethylene glycol (5 mol%) 1.78 g (10 mmol) as a phase transfer catalyst were filtered, washed with dilute alkali, dilute acid and water in turn to neutrality, separated the oil layer, dried with anhydrous magnesium sulfate, and removed ethyl acetate under reduced pressure. After recrystallization, a white solid with a melting point of 73 ~ 76℃ was obtained. Further purification by alumina column chromatography, the melting point is 80 ~ 865438 0℃. The purity of the product synthesized by phase transfer catalysis is about 85%, and the yield of pure product is 82.7%.
Method 3
In the presence of anhydrous sodium carbonate and carbon tetrachloride solvent, 1, 2,4-triazole was chlorinated at 35℃ to obtain 1- chlorine-1, 2,4-triazole, which was used as a chlorine atom donor to react with ketone ether, so that the α position of ketone ether alkyl group was substituted to generate α-. The reaction must be carried out in the presence of initiator such as azodiisobutyronitrile. At the same time, triazole produced by chlorotriazole is precipitated from the reaction solvent. Because the triazole produced by the reaction itself is a pure acid agent, triadimefon will be produced during the reaction. After adding triazole or acid-binding agent, α -chloroketone ether reacts completely.
Upstream and downstream raw materials
Downstream products: triadimenol-> Uniconazole wettable powder
Upstream products: methanol-> Toluene->; Potassium carbonate->; Chlorine->; Formaldehyde->; Hydrazine hydrate->; Formic acid->; Chlorobenzene->; Sulfonyl chloride->; N-pentane->; Emulsifier->; Isoamyl alcohol->; -> ammonium formate; Pinanone->; Trimethoxy phosphorus->; -> 4- chlorophenol; 2-methyl-2-butanol-> EC-> Raw flour->; 3- methyl-1- butene->; Dispersant->; -> 2- methyl -2- butene; 2- methyl-1- butene->; Chlorophenazone->; 1, 1- dichloropinene->; Chlorophenol->; 2- acetoxy-3,4-difluorobenzene->; Chloroether ketone