Tricyclazole
Tricyclazole
CAS: 41814-78-2
Molecular Formula: C9H7N3S
Tricyclazole - Names and Identifiers
Tricyclazole - Physico-chemical Properties
| Molecular Formula | C9H7N3S |
| Molar Mass | 189.24 |
| Density | 1.2292 (rough estimate) |
| Melting Point | 187-188°C |
| Boling Point | 275 °C |
| Water Solubility | 1.6g/L(25 ºC) |
| Appearance | neat |
| BRN | 980261 |
| pKa | 2.40±0.40(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.5500 (estimate) |
| Physical and Chemical Properties | melting point 187-188°C The original drug is an off-white solid with a melting point of 187 -188°C and a vapor pressure of 2.66 6 × 10-5 Pa at 25°C,25°C water solubility of 1.6g/L, chloroform> 33% g/L, dichloromethane. Ethanol 25%, methanol 25%. Stability: not easily decomposed by water and light, also stable to heat (up to 187°C). |
| Use | For the control of rice blast |
Tricyclazole - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| UN IDs | 2588 |
| WGK Germany | 1 |
| RTECS | XZ5475000 |
| HS Code | 29349990 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
Tricyclazole - Upstream Downstream Industry
Tricyclazole - Nature
Open Data Verified Data
pure white crystals, odorless. Melting Point 187~188 deg C, vapor pressure (25 deg C) 2.666 x 10-s Pa. Solubility (%) at 25 ° C: Chloroform 50, dichloromethane 3.3, ethanol 2.5, methanol 2.5, acetone 1, acetonitrile 1, cyclohexanone 1, benzene 0. 42. Xylene 0. 21. N-hexane <0.01. It is stable to light and heat, and is not easy to hydrolyze.
Last Update：2024-01-02 23:10:35
Tricyclazole - Preparation Method
Open Data Verified Data
sulfuric acid was added to o-toluidine in the presence of a solvent, and sodium thiocyanate was Added. The reaction was heated and treated to obtain O-methylphenylthiourea. O-methylphenylthiourea is reacted with chlorine gas in the presence of a solvent, neutralized by addition of a base, cooled, filtered, and spin-dried to give 2-amino-4-methylbenzothiazole. After mixing the appropriate amount of solvent, hydrochloric acid and water, add 2-amino -4-methyl benzothiazole, and the role of hydrazine hydrochloride, temperature reaction to the end, cooling, filtration, after drying, 2-hydrazino-4-methylbenzothiazole was obtained. Then the 2-hydrazino-4-methylbenzothiazole is added to a certain solvent and formic acid under stirring, heated to the end of the reaction, and the solvent and excess formic acid are recovered under reduced pressure, at the same time, water was added to dilute and cool, filter, wash to neutral, spin dry and dry to obtain tricyclazole.
Last Update：2022-01-01 10:12:17
Tricyclazole - Use
Open Data Verified Data
efficient, systemic azole fungicides. Tricyclazole is a kind of systemic fungicide specially used in the prevention and control of rice blast, especially for panicle neck blast. The circulation of rice blast is prevented by inhibiting the infection of rice blast fungus on the surface of plants and the infection points formed in plants. Resistance to other fungicides against the rice blast fungus is also effective. Because the agent also has a protective bactericidal effect, it should be used before the occurrence of the disease.
Last Update：2022-01-01 10:12:17
Tricyclazole - Safety
Open Data Verified Data
The oral LD50 of male rats is 500-545mg/kg, the oral LD50 of dogs is> 50mg/kg, and the percutaneous LD50 of rats is> 5000mg/kg. Rats inhaled LC50> 0.25 mg/L. Mild irritation to rabbit eyes. Rats and mice fed two years Test No effect dose were 275mg/kg, 400mg/kg. No teratogenic, carcinogenic or mutagenic effect was found in animals. No accumulation. No abnormality in reproduction test. The LC50 of carp was 14. 6mg/L (48h), and that of rainbow trout was 7.7mg/L. Safe for bees
Last Update：2022-01-01 10:12:18
Tricyclazole - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| triazole fungicides | tricyclazole, also known as clostriazole, clostriazole, biyan and rice clostriazole, is a selective endosorption protective fungicide developed by Eli Lilly and Company in the United States. BP1419121 patent number, tricyclazole is a protective triazole fungicide with strong endosorption performance, which has special effect in preventing and controlling rice blast, after application, it can be absorbed by the roots, stems, and leaves of rice, and can be transported in the plant. Spray the medicine 1 to 2 times during the entire rice growth period can effectively prevent the occurrence of rice blast. Tricyclazole has strong erosion resistance and does not need to be sprayed in rain after 1 hour of spraying. It mainly inhibits spore germination and attachment spore formation, thereby effectively preventing the invasion of bacteria and reducing the production of spores of Magnaporthe grisea. Tricyclazole has strong internal absorption and operation performance, and decomposes slowly in plants and soil, with a residual period of 7-10 weeks. It can be mixed with seeds, dipped in roots or sprayed on leaves, with good preventive effect. For moderate toxicity to humans and animals, the oral LD50 of rats was 305 mg/kg, and the rats were fed with a diet containing 275 mg/kg for 3 months without adverse effects. The safety interval was 30 days. The residual amount in brown rice was 0.0164~0.1554 mg/kg, which was lower than the allowable residual amount of brown rice in the United States and Japan. The preparation method of tricyclazole: o-toluidine reacts with sulfuric acid and sodium thiocyanate in the presence of a catalyst to generate o-tolyl thiourea; then chlorine gas is passed, closed-loop, o-methylphenylthiourea and chlorine gas Reacts to obtain 7-methyl-2-aminobenzothiazole hydrochloride; the hydrochloride reacts with hydrazine hydrate in the presence of a catalyst to generate 7-methyl-2-hydrazinyl benzothiazole, which undergoes ring expansion with formic acid Reaction, tricyclazole was obtained. |
| toxicity of tricyclazole | tricyclazole is a medium toxic fungicide. The acute oral LD50 of raw powder to rats is 305mg/kg, and that to mice is 250mg/kg. Acute percutaneous LD50>2000mg/kg for rabbits and rats, and acute inhalation of LC50 >0.25mg/L for rats. It has mild irritation to rabbit eyes and skin. Tricyclazole can be quickly metabolized and excreted in animals (rats) without accumulation in vivo. No mutagenic, teratogenic and carcinogenic effects were found under the test conditions. In the reproduction test, there was no abnormality in rats and mice (275mg/kg). The two-year feeding test for rats and mice had no effect doses of 8-24mg/kg-day and 29-46mg/kg-day, respectively. 20% tricyclazole wettable powder has an acute oral LD50 of 1500 mg/kg for male rats and 2440 mg/kg for male mice. the toxicity of tricyclazole to aquatic organisms is low. the acute LC50 of gill carp and rainbow trout is 14. 6 and 7. 7mg/L respectively. For shrimp is 18~32mg/L. No toxic effect on bees and spiders at recommended doses. The mulberry leaves treated with 250mg/L tricyclazole solution were fed to silkworm, which had a slight effect on the weight of silkworm cocoon and egg. Acute LC50>5000mg/L for mallard ducks and quails. 75% tricyclazole wettable powder has an acute oral LD50 of 354 mg/kg in rats, an acute percutaneous LD50 of> 2000 mg/kg in rabbits and an acute inhalation of LC50 of> 3.7 mg/kg in rats. |
| usage | (1) to prevent and control rice seedling blast, use it at the 3-4 leaf stage of seedlings or 5 days before transplanting, use 50-75g (1-1.5 liang) of 20% tricyclazole wettable powder per mu, and add 30-50kg of water to spray evenly. (2) to prevent and control rice leaf blast, when leaf blast has just occurred, 100g (2.2) of 20% tricyclazole wettable powder and 60kg of water are added for spray per mu. The method popularized and applied in Hubei Province is to use 1 750 times of 20% tricyclazole wettable powder, soak the seedlings for one minute, take them out and pile them for half an hour, and then plant them. The control effect of leaf blast is better than that of spray. (3) to prevent and control rice ear blast, at the initial stage of rice break, 75~100 grams (1.5~2 taels) of 20% tricyclazole wettable powder or 30 grams (6 yuan) of 75% tricyclazole wettable powder per mu are sprayed with 60kg of water. Generally, it has an effect of about 80% if it is applied once. If the condition is serious and the climate is conducive to the development of the disease, the effect is better if the medicine is sprayed once in full spike, and the dosage is the same as the first time. |
| analysis method | gas chromatography analysis: gas chromatograph with flame ionization detector (FID), glass column with chromatographic column 0.5 m × 0.003 m (inner diameter), carrier Chromosozb W AN DMCS 60-80 mesh coated with 2% polyethylene glycol succinate stationary solution. Column temperature 195 ℃, gasification temperature 250 ℃, detection chamber temperature 250 ℃. Carrier gas (N2) flow rate 45ml/ min, hydrogen flow rate 40ml/min, air 500ml/min. The internal standard is trichlorocidal alum, without interfering impurities. Under the above chromatographic conditions, the retention time of tricyclazole is about 10min, and triclosan is about 7min. |
| precautions | (1) tricyclazole is a protective fungicide. the first spraying to prevent neck plague should not exceed 3 days after the break at the latest. (2) the daily allowable intake (ADI) of tricyclazole for human body is 0.04 mg/kg/day in Japan and 0.08 mg/kg/day in the United States. The use of tricyclazole should comply with our guidelines for the rational use of pesticide residues in agricultural products. Taking 75% Biyan wettable powder as an example, the maximum residue limit reference value (MRL) is 2 mg/kg in brown rice; The usual dosage is 20g; The maximum dosage is 30g; The maximum number of times of use is 2. The last application is 21 days from the harvest days (safe interval). (3) during use, if liquid medicine splashes into eyes and skin, rinse with plenty of water. In case of accidental poisoning during use, it should be moved to fresh air; oral intake should induce vomiting. No specific antidote, should be symptomatic treatment. (4) this product should be stored in a dry and cool place, and should not be mixed with food, seeds, feed and other pesticides. |
| tricyclazole production process flow chart | o-benzylamine is put into the synthesis kettle, then a proper amount of solvent is added, sodium thiocyanate is put into the synthesis kettle, after stirring evenly, the jacket is cooled with water, sulfuric acid is added dropwise at the temperature of 30~35 ℃, stirring and reacting for half an hour after adding, steam heating and reflux reaction in the jacket is opened for 24 hours, solvent is recovered, and water is added, cooling, filtration, water washing, vacuum suction filtration to dry, resulting in o-methylphenylthiourea. put o-methyl phenylthiourea and solvent into the synthesis kettle, cool, pass in the calculated amount of chlorine, heat preservation reaction for 2 hours, and then recover the solvent. After the solvent is recovered, water is added, cooled, and filtered to obtain 4-methyl-2-aminobenzothiazole hydrochloride. 4-methyl -2-aminobenzothiazole hydrochloride is put into the synthesis kettle, and then the calculated amount of hydrazine hydrate and solvent are added. Under the condition of uniform stirring, the jacket steam is opened and gradually heated to reflux, and the reflux reaction is 8 hours. After the reaction is over, it is cooled, the material is filtered, the filter cake is washed, and the filter cake is sucked to dry with vacuum to obtain 4-methyl-2-hydrazinyl benzothiazole. 4-methyl -2-hydrazinyl benzothiazole was added to the synthesis kettle, and then the calculated amount of formic acid and solvent were added. Under the condition of uniform stirring, the jacket steam is opened and gradually heated to reflux, and the reflux reaction is heated for 8 hours. After the reaction, the solvent is recovered, water is added, cooled, filtered, and dried to obtain the tricyclazole original drug. |
| toxicity | acute oral LD50 of male rats is 358 mg/kg, acute oral LD50 of female and male mice is> 500~545 mg/kg, and oral LD50 of dogs is> 50 mg/kg. Acute percutaneous LD50>5000mg/kg in rats. Rats inhaled LC50>0.25mg/L. Mild irritation to rabbit eyes. Rats and mice were fed at 2-year doses of 275mg/kg and 400mg/kg (8-24mg/kg and 29-46mg/kg per day), respectively. No teratogenic, carcinogenic, mutagenic effect, no accumulation effect, no abnormal reproduction test. Carp LC5014.6 mg/L (48h), trout LC507.7 mg/L. Safe for bees. After treating mulberry leaves with 250mg/kg, the silkworm was fed, which had a slight effect on cocoon weight. |
| use | efficient, systemic azole fungicides. It has special effects on the control of rice blast. It can inhibit spore germination and prevent the rice blast circulation by inhibiting the infection of the rice blast fungus on the surface of the plant and the infection points formed in the plant. Magnaporthe grisea, which is resistant to other fungicides, is also effective. Since the drug also has the function of protective fungicide, it should be used before the disease occurs. The dosage is 3g/100 m2 of 75% wettable powder. In severe cases, it should be sprayed again 18~24 days after the first application. The root can also be soaked with 20~400mg/L liquid medicine for 10min, which can effectively control the occurrence of early leaf blast hazards. tricyclazole is a systemic fungicide specially used to control rice blast, especially for ear neck blast. The dosage of tricyclazole is low (14-27g of effective ingredients per mu), the effective time is long (2-3 weeks), and the preventive effect is good, so it has a strong competitiveness in the pesticide market. used to control rice seedling blast, rice leaf blast, ear neck rice blast and other diseases and insect pests |
| production method | starting from o-toluidine, it is prepared by sodium thiocyanate addition, closed loop, substitution, and ring expansion. Using o-toluidine as raw materials, tricyclazole is prepared by four-step reaction of addition, ring closure, substitution, and ring expansion. Addition reaction Add o-toluidine to sulfuric acid in the presence of a solvent, and then add sodium thiocyanide to heat up the reaction. After solvent recovery, cooling, filtration, drying and other post-treatment, o-methyl phenyl thiourea was obtained, m.p.154 ~ 160 ℃, with a yield of 93% ~ 95%. Ring-closing reaction In the presence of a solvent, o-methylphenylthiourea is reacted with chlorine, and the reaction temperature is controlled. After the heat preservation reaction, the solvent is recovered, alkali is added for neutralization, cooling, filtration, and spin drying to obtain 2-amino-4-methylbenzothiazole. M. p.134 ~ 136 ℃, yield 90% ~ 91%. Substitution reaction After mixing an appropriate amount of solvent, hydrochloric acid and water, add 2-amino-4-methylbenzothiazole, react with hydrazine hydrochloride, heat up the reaction to the end point, cool, filter, and dry to obtain 2-hydrazinyl-4-methylbenzothiazole. M. p. 167~170 ℃, yield 85% ~ 87%. In the ring expansion reaction, 2-hydrazino-4-methylbenzothiazole is added to a reaction kettle with a certain amount of solvent and formic acid under stirring, heated to the end of the reaction, reduced pressure to recover the solvent and excess formic acid, and at the same time Add water to dilute and cool, filter, wash with water to neutral, spin dry and dry to obtain the original tricyclazole drug. M. p. 184~186 ℃, yield 90% ~ 93%. |
| category | pesticide |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 250 mg/kg; Oral-mouse LD50: 245 mg/kg |
| flammability hazard characteristics | thermal decomposition of toxic nitrogen oxide, sulfur oxide gas |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | sand, dry powder, foam |
Last Update：2024-04-10 22:29:15
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Raw Materials for Tricyclazole