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Buprofezin

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Buprofezin Basic information

Product Name:
Buprofezin
CAS:
69327-76-0
MF:
C16H23N3OS
MW:
305.44
EINECS:
614-948-3
Mol File:
69327-76-0.mol
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Buprofezin Chemical Properties

Melting point:
104-106°C
alpha 
22 º (c=8,6N HCl)
Boiling point:
273°C (12 torr)
Density 
1.18
vapor pressure 
1.25 x l0-3 Pa (25 °C)
refractive index 
1.52-1.522
Flash point:
176-178°C
storage temp. 
0-6°C
pka
3.02±0.20(Predicted)
form 
neat
Water Solubility 
0.9 mg/L at 20 ºC
Decomposition 
176-178 ºC
BRN 
8324923
CAS DataBase Reference
69327-76-0(CAS DataBase Reference)
NIST Chemistry Reference
4H-1,3,5-thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl-(69327-76-0)
EPA Substance Registry System
Buprofezin (69327-76-0)
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Safety Information

RIDADR 
UN3077(solid)
WGK Germany 
2
RTECS 
XI2865000
Hazardous Substances Data
69327-76-0(Hazardous Substances Data)
Toxicity
LD50 in mice, rats (mg/kg): 10000, 8740 orally; LC50 (48 hr) in carp: 2-10 mg/l (Kanno, 1981)

MSDS

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Buprofezin Usage And Synthesis

Uses

Buprofezin is a insecticide which works as a chitin synthesis inhibitor. Buprofezin is used to control stubborn rice pests and is effective in controlling green leaf hoppers and white back plant hoppe rs for long durations.

Uses

Insecticide.

Uses

Buprofezin is a contact and ingested insecticide, active against Homoptera (whiteflies, leafhoppers, scale insects, etc.) in and on citrus, cotton, cucumbers, tomatoes, sweet potatoes, rice, etc.

Hazard

Moderately toxic by ingestion. Low toxic- ity by skin contact.

Agricultural Uses

Insecticide, Acaricide, Insect growth regulator: For insect control in food crops and greenhouse ornamentals.

Trade name

APPLAUD®; NNI-750®

Pharmacology

The foregoing indicates that the modes of action of buprofezin and benzoylureas could be similar or identical. However, one differing biochemical effect of buprofezin is inhibition of prostaglandin biosynthesis (33), a mechanism that has been suggested as responsible for its ovicidal activity. Subsequently, the in vitro and in vivo effects of buprofezin were found to be strongly antagonized by 20- hydroxyecdysone (34), which also affected prostaglandin biosynthesis. Thus, inhibition of both prostaglandin and chitin biosynthesis by buprofezin was prevented by 20- hydroxyecdysone, so that both effects of the insecticide are mediated via an effect on the hormone concentration or its receptor. Consequently, buprofezin seems to inhibit the drop in the 20-hydroxyecdysone titer that triggers epidermal cell proliferation, old cuticle digestion, and new cuticle deposition, but the detailed mechanism of this action has yet to be established.

Metabolic pathway

Buprofezin gradually decomposes in soils under flooded and upland conditions, with half-lives of 104 and 80 days, respectively. After 150 days, five degradation products are identified as 2-tert- butylimino-5-(4-hydroxyphenyl)-3-isopropylperhydro- 1,3,5-thiadiazin-4-one, 3-isopropyl-5-phenylperhydro- 1,3,5-thiadiazin-2,4-dione, 1-tert-butyl-3-ispropyl-5- phenylbiuret, 1-isopropyl-3-phenylurea, and phenylurea. As minor products, 2-tert-butylimino-5- phenylperhydro-1,3,5-thiadiazin-4-one or buprofezin sulfoxide are found in the flooded or in the upland soils. Since neither formation of 14CO2 nor hydroxylation is observed in the sterile soils, buprofezin seems to have undergone complete mineralization in soils under both conditions through biological transformation by soil microorganisms.

Degradation

Buprofezin (1) was degraded under acidic conditions with half-lives (DT50) f 6-12 days (pH 4), 34 days (pH 6) and 65 days (pH 10) at 40 °C. Opening of the thiadiazinanone ring appeared to be the primary hydrolytic degradation pathway, to yield 1-tert-butyl-3-isopropyl-5-phenyl-2- thiobiuret (2) and N-isopropyl-N-phenylurea (3) as major products.
Buprofezin is stable to aqueous photolysis. The estimated DT50 of buprofezin in distilled water when exposed to UV light was 39 days. A more complex photodegradation pathway of buprofezin in methanol was reported recently (Datta and Walia, 1997) with DT9 values of 4 hours and 15 days under UV and sunlight irradiation, respectively.

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J & K SCIENTIFIC LTD.
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400-666-7788 010-82848833-
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Shanghai Hanhong Scientific Co.,Ltd.
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021-54306202-
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Chemsky(shanghai)International Co.,Ltd.
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021-50135380
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shchemsky@sina.com
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18981987031 400-1166-196
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Hangzhou Yuhao Chemical Technology Co., Ltd
Tel:
0571-82693216
Email:
info@yuhaochemical.com
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