bifenazate ** D 2341 ** HSDB 7002 ** Translations

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SUMMARY

Bifenazate is an insecticide approved for use in the EU. It has a low water solubility, volatile and would not be expected to leach to groundwater. Bifenate is also not expected to persist in soil or water systems. It is highly toxic to mammals and a recognised skin, eye and respiratory system irritant. It is moderately toxic to most aquatic organisms, honeybees and earthworms.

GENERAL INFORMATION
for bifenazate

Description: An effective, new pesticide for phytophagous mite control

Example pests controlled: Spider mites; Pecan leaf mites; Pacific spider mites; European red mites; Brown almond mite; Six-spotted spider mite

Example applications: Greenhouse crops; Nursery crops; Landscaped areas; Hops; Avocado; Curcubits; Apples & pears; Quince; Egg plants; Cucumbers; Water melon; Strawberries; Tomatoes

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1996, first introduced; 1999, registered USA; 2000, registered UK

EC Regulation 1107/2009 (repealing 91/414):

Status	Approved (RAR active)
Dossier rapporteur/co-rapporteur	Sweden/Italy
Date inclusion expires	31/07/2019
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	-
Chemical formula	C17H20N2O3
Canonical SMILES	CC(C)OC(=O)NNC1=C(C=CC(=C1)C2=CC=CC=C2)OC
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	VHLKTXFWDRXILV-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C17H20N2O3/c1-12(2)22-17(20)19-18-15-11-14(9-10-16(15)21-3)13-7-5-4-6-8-13/h4-12,18H,1-3H3,(H,19,20)
2D structure diagram/image available?	Yes

General status:

Pesticide type	Insecticide, Acaricide
Substance group	Hydrazine carboxylate
Minimum active substance purity	950 g/kg
Known relevant impurities	EU dossier - Toluene 0.7 g/kg
Substance origin	Synthetic
Mode of action	Neuronal inhibitor, non-systemic having contact and residual action. Mitochondrial complex III electron transport inhibitor
CAS RN	149877-41-8
EC number	442-820-5
CIPAC number	736
US EPA chemical code	000586
PubChem CID	176879
Molecular mass (g mol-1)	300.35
PIN (Preferred Identification Name)	propan-2-yl 2-(4-methoxy[1,1'-biphenyl]-3-yl)hydrazinecarboxylate
IUPAC name	isopropyl 3-(4-methoxybiphenyl-3-yl)carbazate
CAS name	1-methylethyl 2-(4-methoxy[1,1'-biphenyl]-3-yl)hydrazinecarboxylate
Other status information	-
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Classification (HRAC)	Not applicable
Herbicide Resistance Classification (WSSA)	Not applicable
Insecticide Resistance Classification (IRAC)	20D
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Tetranychus urticae
Physical state	White to beige coloured crystalline solid as technical material, white as the pure substance
Related substances & organisms	-

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Certis Chemtura Corp.
Example products using this active	Floramite SC Acramite
UK LERAP status	None
Formulation and application details	Often supplied as a suspension concentrated which is mixed with water and applied as a spray.

ENVIRONMENTAL FATE
for bifenazate

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		2.06	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		210700	C4 - Acetone	-
		102000	A5 - Ethyl acetate	-
		44700	A5 - Methanol	-
		24700	A5 - Toluene	-
Melting point (oC)		122	P4	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		240	A5	-
Flashpoint (oC)		Not expected to self-ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	2.51 X 1003	Calculated	-
	Log P	3.4	A5	High
Bulk density (g ml-1)/Specific gravity		1.31	P4	-
Dissociation constant (pKa) at 25oC		12.94	A5	-
		Note: Strong base
Vapour pressure at 20oC (mPa)		1.33 X 10-02	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		1.01 X 10-03	A5	Non-volatile
GUS leaching potential index		-0.23	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.72 X 10-04	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution: 206nm = 272686, 232nm = 25058, 264nm = 12413, 290nm = 6186 shoulder	A5	-
Surface tension (mN m-1)		61.6	A5	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	0.69	A5	Non-persistent
	DT50 (lab at 20oC)	0.69	A5	Non-persistent
	DT50 (field)	4.8	A3	Non-persistent
	DT90 (lab at 20oC)	1	A5	-
	DT90 (field)	-	-	-
	DT50 modelling endpoint	-	-	-
	Note	EU dossier (RAR 2016) lab studies DT50 range <1 - 6.0 days, DT90 range 0.3-12.3 days n=4
Dissipation rate RL50 on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL50 on and in plant matrix	Value	1.2	R3	-
	Note	Tea shoots, n=1
Aqueous photolysis DT50 (days) at pH 7	Value	0.85	A5	Fast
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	0.51	A5	Non-persistent
	Note	pH sensitive: DT50 8.2 days at pH 4, 4.8 days at pH 5, 0.51 days at pH 7 and 0.04 days at pH 9 all at 25 degC
Water-sediment DT50 (days)		0.045	A5	Fast
Water phase only DT50 (days)		0.45	A5	Fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	A4	Slightly mobile
	Koc	1778
	Notes and range	-
Freundlich	Kf	7.0	A5	Moderately mobile
	Kfoc	368
	1/n	1.16
	Notes and range	EU dossier (2016 RAR) Kf range 4.4-14.6 mL/g, Kfoc range 243-628 mL/g, 1/n range 1.00-1.24, Soils=4
pH sensitivity		None

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
diazinecarboxylic acid, 2-(4-methoxy-(1,1-biphenyl)-3-yl),1-methylethyl ester (Ref: D-3598)		Soil	0.855	Major fraction, Relevant
4-methoxybiphenyl (Ref: D-1989)		Soil	0.333	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
4-hydroxybiphenyl	-	Rat	-	-
4,4-biphenyl	-	Rat	-	-
3,4-dihydroxy-[1,1'-biphenyl] (Ref: D-9472)	-	Water (Photolysis)	-	-
(Ref: D-9963)	-	Water (Photolysis)	-	-

ECOTOXICOLOGY
for bifenazate

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	83	E3	Low potential
	CT50 (days)	Not available		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	> 0.9	A5 Dog	High
	(ppm diet)	> 40		-
Birds - Acute LD50 (mg kg-1)		1036	A5 Colinus virginianus	Moderate
Birds - Short term dietary (LC50/LD50)		686 mg kg feed-1	A5 Anas platyrhynchos	-
Fish - Acute 96 hour LC50 (mg l-1)		0.58	A5 Lepomis macrochirus	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		0.017	A5 Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.5	J4 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.15	A5 Daphnia magna	Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		0.058	P4 Americamysis bahia	High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		-	-	-
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.3	A5 Skeletonema costatum	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	8.50	A5 Apis mellifera	Moderate
	Oral acute 48 hour LD50 (μg bee-1)	> 100	A5 Apis mellifera	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 429	A5 Eisenia foetida	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	Moderately harmful	Q2 Parasitoids	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	-	-	-
Soil micro-organisms		-	-	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for bifenazate

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)		> 5000	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	L3 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 4.4	L3 Rat, 4 hr (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.01	JMPR 2006	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		Not allocated	JMPR 2006	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.0036	A5 Rat, 90 day, SF=100	-
Dermal penetration studies (%)		1-2	A5 concentration dependent	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	-
	Occupational	Occupational exposure may occur through inhalation of dust and dermal contact
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		Harmful if ingested

: 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 IMDG Transport Code is usually 9
CLP classification 2013		Health: H372, H317
EC Risk Classification		Xn - Harmful: R43 Xi - Irritant: R36
EC Safety Classification		S26, S36/37
WHO Classification		U	-	Unlikely to present an acute hazard
US EPA Classification (formulation)		III	-	Caution - Slightly toxic
UN Number		Usually 3082
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for bifenazate

Language	Name
English	bifenazate
French	bifenazate
German	Bifenazat
Danish	bifenazat
Italian	bifenazate
Spanish	bifenazato
Greek	-
Slovenian	bifenazat
Polish	bifenazat
Swedish	bifenazat
Hungarian	-
Dutch	-

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Record last updated: Monday 13 May 2019
Contact: aeru@herts.ac.uk