buprofezin (Ref: PP 618) ** buprofezine ** NNI 750 ** ST-29285 ** Translations

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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

Chemical structure:

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

General status:

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	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		Value	Source/Quality Score/Other Information	Interpretation
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		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	Value	1.15 X 10-02	Calculated	-
	Note	-
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		Value	Source/Quality Score/Other Information	Interpretation
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		Value	Source/Quality Score/Other Information	Interpretation
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		Value	Source/Quality Score/Other Information	Interpretation
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		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:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		Not explosive or oxidising
CLP classification 2013		Environment: H411
EC Risk Classification		N - Dangerous for the environment: R50, R53
EC Safety Classification		-
WHO Classification		III	-	Slightly hazardous
US EPA Classification (formulation)		III	-	Caution - Slightly toxic
UN Number		-
Waste disposal & packaging		-

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

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Record last updated: Thursday 13 September 2018
Contact: aeru@herts.ac.uk
© University of Hertfordshire