INTERNATIONAL UNION
   OF PURE AND APPLIED
   CHEMISTRY
contact
buprofezin (Ref: PP 618)
** buprofezine ** NNI 750 ** ST-29285 ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status 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: Click to access a note on the approvals information on this site

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

Chemical structure: Click here for further information on the general chemical status information used on this site
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-
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
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:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Certis
  • Nihon Nohyaku
  • Nichino America
  • Aventis
  • Syngenta
Example products using this active
  • Applaud
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details Usually supplied as a soluble concentrate that is mixed with water and applied as a spray.


ENVIRONMENTAL FATE

for buprofezin

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 0.46 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 520000 B4 - Chloroform -
336000 A5 - Toluene -
253000 A5 - Acetone -
241000 A5 - Ethyl acetate -
Melting point (oC) 105.1 A5 -
Boiling point (oC) 252 A5 -
Degradation point (oC) 177 L3 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 8.51 X 1004 Calculated -
Log P 4.93 A5 High
Bulk density (g ml-1)/Specific gravity 1.18 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.042 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 2.8 X 10-02 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 0.58 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 1.15 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated High
Maximum UV-vis absorption L mol-1 cm-1 Neutral solution: 245nm = 11515; [Acidic solution: 229nm = 16463; [Basic solution: 220nm = 9240, 245nm = 11650 A5 -
Surface tension (mN m-1) 70.4 A5 at 20oC -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 50 B4 Moderately persistent
DT50 (lab at 20oC) 135.4 A5 Persistent
DT50 (field) 45.6 A5 Moderately persistent
DT90 (lab at 20oC) 333 A5 -
DT90 (field) 155 A5 -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 range 32-322 days, DT90 range 107-1071 days, field studies DT50 range 37.5-63 days, DT90 range 124-208 days; Other studies: Lab DT50 range 26-274 days, field DT50range 48-63 days
Dissipation rate RL50 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value 7.4 R4 -
Note Published literature RL50 range 3.5-16.3 days, 7 field and undercover grown crops, various matrices, n=11; Peppers in cold storage RL50=253 days
Aqueous photolysis DT50 (days) at pH 7 Value 33 A5 Stable
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note DT50: 51 days at pH 5, 378 days at pH 7, 396 at pH 9
Water-sediment DT50 (days) 49 A5 Moderately fast
Water phase only DT50 (days) 16.8 A5 Slow

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd 103 A5 Non-mobile
Koc 5363
Notes and range EU dossier Kd range 4.27-318.12 mL/g, Koc range 854-21208 mL/g, Soils=7
Freundlich Kf 98.35 A5 Non-mobile
Kfoc 5334
1/n 1.00
Notes and range EU dossier Kf range 10.52-276.82, Kfoc range 2157-19091 mL/g, 1/n range 0.75-1.28; Other study Kf = 750 mean of 7 values. Clay OC=3.8% Kf=39.94; Sandy loam OC=2.7% Kf=303.9; Sand OC=0.5% Kf=1.98
pH sensitivity No

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 - -


ECOTOXICOLOGY

for buprofezin

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 509 A5 Whole fish Threshold for concern
CT50 (days) 0.5 -
Mammals - Acute oral LD50 (mg kg-1) > 2198 B5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) > 3.6 B5 Rat High
(ppm diet) > 40 -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Anas platyrhynchos Low
Birds - Short term dietary (LC50/LD50) > 1306 mg kg bw-1 day-1 A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) > 0.33 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.052 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 0.42 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.08 A5 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) 0.1 A5 Chironomus riparius Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) 0.17 A5 Chironomus riparius Moderate
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 2.33 F4 Lemna gibba Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) > 2.1 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 200 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 163.5 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 250 A5 Eisenia foetida, corr Low
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 3000 A5 Typhlodromus pyri -
% Effect Harmless Mortality
Dose: field rate
A5 Typhlodromus pyri
-
Other arthropod (2) LR50 g ha-1 Harmless Dose: 180 g ha-1
AA3 Chrysoperla carnea
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 5 kg ha-1
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for buprofezin

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the 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:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
CLP classification 2013 Environment: H411
EC Risk Classification Click here to view information omn the EU risk phrases N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases -
WHO Classification III - Slightly hazardous
US EPA Classification (formulation) III - Caution - Slightly toxic
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for buprofezin

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