buprofezin (Ref: PP 618) |
![]() |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION
for buprofezin
Description: A moulting inhibitor, thiadiazine insecticide for whitefly and other insect control
Example pests controlled: Whitefiles, Leaf- and plant-hoppers, Scale insects, Lady beetles, Mealybugs
Example applications: Citrus crops; Top fruit; Cucumbers; Tomatoes; Sweet potatoes; Rice; Cotton
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1981, first reported; 1984 first introduced
EC Regulation 1107/2009 (repealing 91/414):
Status | Approved |
Dossier rapporteur/co-rapporteur | Italy/Austria |
Date inclusion expires | 31/01/2023 |
EU Candidate for substitution (CfS) | No |
Listed in EU database | Yes |
Approved for use () or known to be used (
) in the following European countries:
AT |
BE |
BG |
CY |
CZ |
DE |
DK |
EE |
EL |
ES |
FI |
FR |
HR |
HU |
IE |
IT |
LT |
LU |
LV |
MT |
NL |
PL |
PT |
RO |
SE |
SI |
SK |
UK |
Also used in: Australia, USA
Isomerism | Theoretically can exists in both the Z- and E- form, but X-ray analysis indicates that buprofezin consists of the Z-isomer exclusively (both in solid and in dissolved state). |
Chemical formula | C16H23N3OS |
Canonical SMILES | CC(C)N1C(=NC(C)(C)C)SCN(C1=O)C2=CC=CC=C2 |
Isomeric SMILES | No data |
International Chemical Identifier key (InChIKey) | PRLVTUNWOQKEAI-VKAVYKQESA-N |
International Chemical Identifier (InChI) | InChI=1S/C16H23N3OS/c1-12(2)19-14(17-16(3,4)5)21-11-18(15(19)20)13-9-7-6-8-10-13/h6-10,12H,11H2,1-5H3/b17-14- |
2D structure diagram/image available? | Yes |
Pesticide type | Insecticide, Acaricide | |||
Substance group | Unclassified | |||
Minimum active substance purity | 985 g/kg | |||
Known relevant impurities | EU dossier - None declared | |||
Substance origin | Synthetic | |||
Mode of action | Contact and stomach action. Inhibitors of chitin biosynthesis. | |||
CAS RN | 69327-76-0 | |||
EC number | - | |||
CIPAC number | 681 | |||
US EPA chemical code | 275100 | |||
PubChem CID | 50367 | |||
Molecular mass (g mol-1) | 305.44 | |||
PIN (Preferred Identification Name) | (2Z)-2-(tert-butylimino)-5-phenyl-3-(propan-2-yl)-1,3,5-thiadiazinan-4-one | |||
IUPAC name | (Z)-2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one | |||
CAS name | 2-((1,1-dimethylethyl)imino)tetrahydro-3-(1-methylethyl)-5-phenyl-4H-1,3,5-thiadiazin-4-one | |||
Other status information | - | |||
Relevant Environmental Water Quality Standards | - | |||
Herbicide Resistance Classification (HRAC) | Not applicable | |||
Herbicide Resistance Classification (WSSA) | Not applicable | |||
Insecticide Resistance Classification (IRAC) | 16 | |||
Fungicide Resistance Classification (FRAC) | Not applicable | |||
Examples of recorded resistance | Bemisia tabaci Trialeurodes vaporariorum Nilaparvata lugens |
|||
Physical state | White crystalline powder | |||
Related substances & organisms | - |
Formulations:
ENVIRONMENTAL FATE
for buprofezin
Other known metabolites:
Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
3-isopropyl-5-phenylperhydro-1,3,5-thiadiazin--2,4-dione Note: Mol wt = 250.3; Rat LD50(oral) = 300-2000 |
BF9 | Plant; Animal; Rat | - | - |
1-tert-butyl-3-isopropyl-5-phenylbiuret Note: Rat LD50(oral) >2000 |
BF11 | Plant | - | - |
N-isopropyl-N-phenylurea Note: Mol wt = 178.1; Rat LD50(oral) = 300-2000 |
BF12 | Plant; Animal | - | - |
1-tert-butyl-3-isopropy-5-phenyl-2-biuret Note: Rat LD50(oral) = 300-2000 |
BF25 | Plant | - | - |
2-amino-2-methylpropyl-2-isopropyl-4-phenylallophanate Note: Mol wt = 293.4; Rat LD50(oral) = 50-300 |
BF26 | Plant | - | - |
- | buprofezin sulphoxide; BF10 | Water/sediment | - | - |
2-(2-hydroxy-1,1-dimethylethyl)imino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-1H-1,3,5-thiadiazin-4-one Note: Rat LD50(oral) range 300-2000 |
BF4 | Plant; Rat | - | - |
HUMAN HEALTH AND PROTECTION
for buprofezin
General:
Property ![]() |
Value | Source/Quality Score/Other Information ![]() |
Interpretation ![]() |
|
Threshold of Toxicological Concern (Cramer Class) ![]() |
High (class III) | - | - | |
Mammals - Acute oral LD50 (mg kg-1) | > 2198 | B5 Rat | Low | |
Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
Mammals - Inhalation LC50 (mg l-1) | > 4.57 | A5 Rat, 4 hr | - | |
Other Mammal toxicity endpoints | - | - | ||
ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.01 | A5 Rat, SF=100 | - | |
ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.5 | A5 Rat, SF=100 | - | |
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.04 | A5 Dog, SF=100 | - | |
Dermal penetration studies (%) | 40 | A5 | - | |
Dangerous Substances Directive 76/464 | - | - | - | |
Exposure Limits | - | - | - | |
Exposure Routes | Public | Acceptable risk for proposed uses | ||
Occupational | Acceptable risk for proposed uses | |||
European MRLs | Click here for the EU MRL pesticide database | |||
Drinking Water Standards | - | - | - | |
Drinking Water MAC (μg l-1) | - | - | - |
Health issues:
Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
- |
- |
|
||||||
General human health issues | No further information available |
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
Language | Name |
English | buprofezin |
French | buprofezine |
German | Buprofezin |
Danish | buprofezin |
Italian | buprofezin |
Spanish | buprofezin |
Greek | - |
Slovenian | buprofezin |
Polish | buprofezyna |
Swedish | buprofezin |
Hungarian | buprofezin |
Dutch | buprofezin |
Record last updated: Thursday 13 September 2018
Contact: aeru@herts.ac.uk
© University of Hertfordshire