4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl-
Buprofezin
CAS: 69327-76-0
Molecular Formula: C16H23N3OS
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Names and Identifiers
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Physico-chemical Properties
| Molecular Formula | C16H23N3OS |
| Molar Mass | 305.44 |
| Density | 1.18 |
| Melting Point | 104-106°C |
| Boling Point | 273°C (12 torr) |
| Specific Rotation(α) | 22 º (c=8,6N HCl) |
| Flash Point | 176-178°C |
| Water Solubility | 0.9 mg/L at 20 ºC |
| Solubility | Chloroform (Slightly), Methanol (Slightly) |
| Vapor Presure | 1.25 x l0-3 Pa (25 °C) |
| Appearance | neat |
| Color | White to Pale Beige |
| BRN | 8324923 |
| pKa | 3.02±0.20(Predicted) |
| Storage Condition | 0-6°C |
| Sensitive | Sensitive to light |
| Refractive Index | 1.52-1.522 |
| MDL | MFCD01681899 |
| Physical and Chemical Properties | Density 1.18 melting point 104-106°C boiling point 273°C (12 torr) decomposition temperature 176-178°C refractive index 1.52-1.522 flash point 156°C specific rotation 22 ° (c = 8,6N HCl) water-soluble 0.9 mg/L at 20°C |
| Use | Can effectively control the rice cicadaceae and planthopidaceae, potato on the leaf cicadaceae, citrus, cotton, vegetables on the whiteflies and other pests |
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Risk and Safety
| UN IDs | UN3077(solid) |
| WGK Germany | 2 |
| RTECS | XI2865000 |
| Toxicity | LD50 in mice, rats (mg/kg): 10000, 8740 orally; LC50 (48 hr) in carp: 2-10 mg/l (Kanno, 1981) |
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Upstream Downstream Industry
| Raw Materials | Monomethylaniline N-T-Butyl-N'-Isopropylthiourea Toluene Ammonium thiocyanate Chlorine tert-Butanol Carbon tetrachloride Isopropylamine |
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Nature
Open Data Verified Data
pure white crystals. Melting point of 10 6.1 C, vapor pressure (25 C) 1.25 x 10-3pa, d1,18. Solubility at 25 °c (g/L): acetone 240, chloroform 520, ethanol 80, toluene 320, 0. 9mg/L in water. It is stable to acid, alkali, light and heat.
Last Update：2024-01-02 23:10:35
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Preparation Method
Open Data Verified Data
The intermediate N-chloromethyl-N-phenylcarbamoyl chloride was prepared by the reaction of N-methylaniline with phosgene and chlorine, tert-butyl isocyanate was obtained by translocation, and then reacted with isopropylamine to obtain 1-isopropyl-3-tert-butylthiourea. This compound is reacted with the above-mentioned N-chloromethyl-N-phenylcarbamoyl chloride in the presence of a base to give Buprofezin.
Last Update：2022-01-01 10:11:47
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Introduction
Stable to acid, alkali, light and heat.
Last Update：2022-10-16 17:27:59
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Use
Open Data Verified Data
The thiadiazine insect growth regulator is a new type of highly selective insecticide. It has the characteristics of high activity, high selectivity and long residual effect. It is an Insect molting inhibitor that acts by inhibiting chitin synthesis and interfering with metabolism. It has special effects on planthopper, leaf hopper and whitefly, and also has good effects on some scale insects such as Veratrum botrytis and Veratrum, mainly used for controlling rice leaf hopper and planthopper, potato leaf hopper, citrus, cotton and vegetable whitefly, citrus Turcz and Silla.
Last Update：2022-01-01 10:11:48
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Safety
Open Data Verified Data
oral LD50 of male rats. 2198mg/kg, 2355mg/kg for females, rat percutaneous LD50>5000mg/kg, inhalation LC50> 4.57 mg/L. Slight irritation to eyes and skin. The non-effective dose was 0. 9-1. 12mg/kg per day in rats fed for two years. Quail LD50 >15000mg]kg, carp LC50 2.7mg/L, Daphnia LC50>50. 6mg/L, at the dose of 2000mg/L, no direct effect on bees. It is safe for silkworm and natural enemies.
Last Update：2022-01-01 10:11:49
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl- - Reference Information
| Decomposition | 176-178 ºC |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| insecticide | Buprofezin was first developed by the Japanese pesticide company and is a new type of selective insecticide that inhibits the growth and development of insects, the effect of contact is strong, and it also has the effect of stomach poison. The mechanism of action is to inhibit the synthesis of chitin and interfere with the metabolism of insects, resulting in the deformity of nymphs or the deformity of adult wings and slow death. General application after 3 ~ 7d can be effective, no direct killing of adult, but can shorten the life span, reduce the amount of eggs, and the output is sterile eggs, even if the larvae hatch also soon died. Buprofezin has a high selectivity, and has a good control effect on the planthoptera, the Leaf, the whitefly and the scale insect pests, and also has a long-lasting larvicidal activity against some coleopteran pests and mites. It can effectively control planthopper and leaf hopper on rice, leaf hopper on tea, potato, whitefly on citrus, vegetable, and shield and powder on citrus, can also control fruit trees and tea tree on the scale of insects. Efficacy for more than 30 days. The natural enemies of pests are relatively safe and the comprehensive effect is good. There was no interaction with other insecticides. According to China's pesticide toxicity grading standards, Buprofezin is a low toxicity insecticide. The acute oral LD50 for male and female rats was 2198mg/kg body weight and 2355mg/kg body weight respectively. Irritation of the eyes and skin is minimal. There was no teratogenic, mutagenic and carcinogenic effect in the test dose, no abnormality was found in the two generation breeding test, and the toxicity to fish and birds was low. |
| Usage | foliar spray, 50 ~ 600gAI/ha; Foliar spray powder, 450 ~ 600g/ha; submerged application, 600-800g/ha. For example, 25% Buprofezin wettable powder 375 ~ 750g/ha dose can control planthopper, leaf hopper, greenhouse whitefly on rice and vegetables, 800 ~ 1000g/ha can control fruit trees and tea on the scale of the insect. The sustained effect period is 35 ~ 40d, which is safe for natural enemies and flower-visiting insects, and has no interactive resistance with other insecticides, but the effect is slow, and the pest hazard can be controlled 3 ~ 7d after application, therefore, when the population density is high, it should be mixed with quick-acting insecticides. 1. Prevention and Control of rice pests: (1) rice planthopper and leafhopper: spray once at the beginning of the young nymphs of the main pest generation, and use 20-30g (5-7.5g) of youlede 25% wettable powder per mu, add water 5-10kg, low-volume spray or add water 40- 50kg constant spray, focus on the lower part of the spray plant. ② Buprofezin is used to control brown planthopper in rice, 20-30g/mu, 25% wettable powder is used to control brown planthopper in the main generation and its previous generation, in the egg incubation period to the young nymphs period, add water to the main activities of pests in the damaged parts (the middle and lower part of the rice plant) for 1 times of uniform spray, can effectively control the damage. In the initial peak period of the nymphs of the main harmful generation of brown planthopper, the application can also treat the white-backed planthopper and the leaf hopper, and the effect can reach 81-100%. 2. Prevention and Control of Fruit Pests: Control of citrus verrucifera, in the young nymphs peak period, with 25% wettable powder 1500~2000 times liquid (125 ~ 167mg/kg) uniform spray, the effect is good. 3. Prevention and Control of tea pests: Prevention and Control of tea small green leaf cicada, black whitefly, albino, tea orange gall mites, etc., in the tea non-picking period and young nymphs or if the mite peak period and the density of mites is high, 25% ~ 750 times of Buprofezin wettable powder (1000~250 mg/kg) was used. In the low density of mites, with 1000~1500 times of liquid (167 ~ 250mg/kg) uniform spray, can effectively control the harm of insects and mites. 4. Buprofezin control greenhouse cucumber, tomato and other vegetables whitefly, in the young nymphs peak period, with 25% wettable powder 2000~2500 times liquid (100 ~ 125mg/kg) uniform spray, it has good control effect, and can also treat tea yellow mites and so on. |
| analytical method | 1. Product Analysis: The sample is extracted with chloroform, with dicyclo hexyl phthalate or two tridecane as internal standard substance, using stainless steel column and hydrogen flame ionization detector with 5% OV-101/ Gas CHRO Q as filler, separation and determination of Buprofezin by gas chromatography. 2. Residue Analysis: Gas chromatography (GC method) or high performance liquid chromatography (HPIC method) (Liu, 1991, pesticides. 30(1):21). |
| allowable residue | China recommends the maximum allowable amount of 0.02mg/kg body weight: the maximum allowable residue is 0.3mg/kg, and the maximum residue limit (MRL) recommended in Japan is 0.3mg/kg for brown rice. |
| toxicity | Acute oral LD50 of male rats was 2198mg/kg, female was 2355mg/kg, acute percutaneous LD50>5000mg/kg, acute inhalation LC50>4.57mg/L. Slight irritation to eyes and skin. The dose of no effect in the 2-year feeding test of rats was 0.9-1.12mg/kg per day. Ames or Rectus test results were negative. No teratogenic, carcinogenic or mutagenic phenomena were found, and no abnormality was found in two generations of animal breeding test. Quail LD50>15000mg/kg, carp LC50 2.7mg/L, Daphnia LC50>50.6mg/L, in the 2000mg/L dose, no direct effect on bees. It is safe for silkworm and natural enemies. |
| Use | thiadiazine insect growth regulator, Insect molting inhibitor. By inhibiting the synthesis of chitin and interfering with metabolism, the pests can not be normal molting and metamorphosis and gradually die. It has the characteristics of high activity, high selectivity and long residual period. It has special effects on planthopper, leaf hopper and whitefly, and also has good effects on some scale insects such as Veratrum botrytis and Veratrum, mainly used for controlling rice leaf hopper and planthopper, potato leaf hopper, citrus, cotton and vegetable whitefly, citrus Turcz and Silla. Such as the control of rice brown planthopper, in the egg incubation period to the young nymphs full-onset period, with 25% wettable powder 3~4.5g/100, the water in the main activities of pests harmful parts spray, and can also cure the white-backed planthopper, leaf hopper, etc. To control the small green leaf cicada, black whitefly, flower orange mite, etc., in the non-picking period of tea and insect low age with 25% wettable powder 750~1500 times liquid spray. The drug is sensitive to cabbage and radish, and should be paid attention to when using it. This product is a new type of highly selective insecticide. 6.6-13.3G active ingredients per mu, can control rice and vegetables on the planthopper, leaf hopper, greenhouse whitefly and other pests; 53.3-66.6G active ingredients per mu, can control fruit trees and tea on the scale insects and other pests. it can effectively control the middle cicadaceae and planthopidaceae on Rice, the leaf cicadaceae on potato, citrus, cotton, whiteflies and other pests on vegetables |
| production method | The intermediate N-chloromethyl-N-phenylcarbamoyl chloride is obtained by reacting N-methylaniline with phosgene and chlorine; in the presence of an acid, tert-butyl alcohol is reacted with ammonium thiocyanate, then tert-butyl isocyanate is obtained by translocation, and then reacted with isopropylamine to obtain 1-isopropyl-3-tert-butylthiourea. The latter is reacted with the above-mentioned N-chloromethyl-N-phenylcarbamoyl chloride in the presence of a base to give Buprofezin. Buprofezin is a pale or pale yellow crystalline powder. The content of active ingredient of first grade product is more than or equal to 95.0%, and that of qualified product is more than or equal to 90.0%. Raw material consumption quota: tert-butyl alcohol (85%)600kg/t, N-methyl aniline (99%)800kg/t, isopropylamine (98%)350kg/t. preparation of non-phosgene synthesis of Feth butyl isothiocyanate after mixing 74.1G of tert-butyl alcohol, 600ml of water and 95.1G of ammonium thiocyanate, heating to 75 ℃, 200ml of concentrated hydrochloric acid was added dropwise to the reaction solution within 30min, the temperature was then increased to 85 °c and the reaction was stirred for 5h at this temperature. The temperature of the reaction solution was lowered to about 30 ° C., and allowed to stand, the water layer was separated, and the oil layer was washed with water to obtain 103g of yellow oil. 98.5g of 80 ° C./16kPa fraction was collected under reduced pressure, and the yield was 86.7%. Preparation of N-tert-butyl-N'-isopropylthiourea after mixing 24.8g (content 92.8%) of tert-butyl Isothiocyanate and 70ml of toluene, the reaction solution was cooled to 10 °c, A solution of 13.1g of isopropylamine and 10ml of toluene was added dropwise to the reaction solution under stirring, and the reaction temperature was not more than 20 ° C., then stirred at room temperature for 3H, filtered, washed with toluene and dried to obtain 33.5g of product, m.p.140 ~ 145 °c (recrystallization from ethanol, m.p.149 ~ 150), the content of 97.0%, the yield of 93.4%. It has also been reported that 0.3mol tert-butyl Isothiocyanate and 0.32mol isopropylamine were dissolved in 70mL petroleum ether and reacted at room temperature for 24h, and the yield was 97%. Preparation of N-methyl-N-phenylformamide 56.0g of N-methylaniline, 85% g (content) of formic acid and ML of toluene were heated and refluxed for 3~4H, the reflux liquid was allowed to pass through. Toluene and excess formic acid were distilled off as much as possible under reduced pressure to obtain 110g of crude product. 110g of 113-0.8 °c/98.0-0.9kPa fraction was collected under reduced pressure, M.P. 13~14 C, the yield of 90.7%. Preparation of N-chloromethyl-N-phenylcarbamoyl chloride 1.5g (content 76.8) of N-methyl-N-phenylformamide, 89.1% of carbon tetrachloride and 3g of azoisobutyronitrile, under stirring, chlorine gas was slowly introduced, and the reaction temperature was controlled to rise to reflux within 15min, and the chlorine gas was about 100g in 1H. Carbon tetrachloride was distilled off to obtain 108g of crude oil, which became a solid by coagulation. It was m. P. 35~40 °c (recrystallized from n-hexane, m. P. 46~47 °c), with a content of 88.7% and a yield of 93.2%. Synthesis of Buprofezin a solution of 11.5g of N-chloromethyl-N-phenylcarbamoyl chloride in 10ml of toluene was added dropwise, in the reaction solution of toluene and 9.0g of N-tert-butyl-N'-isopropylthiourea, the temperature was controlled not to exceed 25 °c, and then stirred at room temperature for 3H, at 80 °c for 2H, cool to room temperature. Solid sodium chloride was dissolved by adding 25ml of water, allowed to stand, the aqueous layer was separated, the organic phase was removed of toluene under reduced pressure, and the residue was added with 80ml of 80% ethanol, stirred, cooled, filtered and dried to give product 10.8g of white solid, m. P. 98~102 °c (recrystallization from ethanol, m. P. 104~106 ℃), the content of 93.5%, the yield of 66.3%. N-chloromethyl-N-phenylcarbamoyl chloride was prepared by the reaction of N-methylaniline with phosgene and chlorine by phosgene synthesis, and then reacted with 1-isopropyl-3-tert-butylthiourea in the presence of triethylamine, synthesis of Buprofezin. |
| category | pesticide |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 2198 mg/kg; Oral-mouse LD50: 5000 mg/kg |
| flammability hazard characteristics | toxic nitrogen oxide and sulfur oxide gases from combustion |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials |
| extinguishing agent | dry powder, foam, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:52
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Product Name: Buprofezin Visit Supplier Webpage Request for quotationCAS: 69327-76-0
Tel: 18301782025
Email: 3008007409@qq.com
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Multiple Specifications
Product Name: Buprofezin Visit Supplier Webpage Request for quotationCAS: 69327-76-0
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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Raw Materials for 4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl-