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69327-76-0

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Identification

Name
Buprofezin
CAS
69327-76-0
Synonyms
2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl-4h-1,3,5-thiadiazin-4-one
2-TERT-BUTYLAMINO-3-ISOPROPYL-5-PHENYL-1,3,5-THIADIAZINAN-4-ONE
2-(tert-Butylimino)-3-isopropyl-5-phenylperhydro-1,3,5-thidiazin-4-one
APPLAUD
APPLAUD(R)
BUPROFENZIN
BUPROFEZIN
BUPROLEX
BUTYL
NNI 750
VIAPPLA
(2Z)-2-([(Z)-1,1-Dimethylethyl]imino)-3-isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one
2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl-4h-1,3,5-t
2-tert-Butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one
2-tert-Butylimino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one
2-tert-Butylimino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiodiazin-4-one
2-tert-Butylimino-3-isopropyl-5-phenylperhydro-1,3,5-thiadiazinan-4-one
3,5-Thiadiazin-4-one,2-[(1,1-dimethylethyl)imino]tetrahydro-3-(1-methylethyl)-5-phenyl-4H-1
4H-1,3,5-Thiadiazin-4-one, 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl-
4h-1,3,5-thiadiazin-4-one,2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylet
EINECS(EC#)
614-948-3
Molecular Formula
C16H23N3OS
MDL Number
MFCD01681899
Molecular Weight
305.44
MOL File
69327-76-0.mol

Chemical Properties

Melting point 
104-106°C
mp 
104-106°C
alpha 
22 º (c=8,6N HCl)
Boiling point 
273°C (12 torr)
bp 
273°C (12 torr)
density 
1.18
vapor pressure 
1.25 x l0-3 Pa (25 °C)
refractive index 
1.52-1.522
Fp 
176-178°C
storage temp. 
0-6°C
form 
neat
pka
3.02±0.20(Predicted)
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
69327-76-0(EPA Substance)

Safety Data

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)

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

msds information
NNI 750(69327-76-0).msds

Hazard Information

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