tebufenozide (Ref: RH 5992 2F ) ** tebufenoxide ** tebufonozide ** Translations

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GENERAL INFORMATION
for tebufenozide

Description: An insecticide used to control Lepidopterous larvae in a wide variety of cropping situations

Example pests controlled: Grape berry moth; Codling moth; European grapevine moth; Grape leafroller; Vine moth; Apple brown tortrix moth;

Example applications: Fruit including grapes, apples, pears, berries

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1994

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

Status	Approved
Dossier rapporteur/co-rapporteur	Spain/Germany
Date inclusion expires	31/05/2021
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

Chemical structure:

Isomerism	-
Chemical formula	C22H28N2O2
Canonical SMILES	CCC1=CC=C(C=C1)C(=O)NN(C(=O)C2=CC(=CC(=C2)C)C)C(C)(C)C
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	QYPNKSZPJQQLRK-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C22H28N2O2/c1-7-17-8-10-18(11-9-17)20(25)23-24(22(4,5)6)21(26)19-13-15(2)12-16(3)14-19/h8-14H,7H2,1-6H3,(H,23,25)
Structure diagram/image available?	Yes

General status:

Pesticide type	Insecticide
Substance group	Diacylhydrazine
Minimum active substance purity	970 g/kg
Known relevant impurities	EU dossier: t-butyl hydrazine <0.001 g/kg
Substance origin	Synthetic
Mode of action	Accelerates molting, mainly stomach action
CAS RN	112410-23-8
EC number	412-850-3
CIPAC number	724
US EPA chemical code	129026
PubChem CID	91773
Molecular mass (g mol-1)	352.47
PIN (Preferred Identification Name)	N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide
IUPAC name	N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide
CAS name	3,5-dimethylbenzoic acid 1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide
Other status information	-
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Classification (HRAC)	Not applicable
Herbicide Resistance Classification (WSSA)	Not applicable
Insecticide Resistance Classification (IRAC)	Not known
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Cydia pomonella Planotortrix octo Plutella xylostella Spodoptera exigua Spodoptera littoralis
Physical state	Off-white powder
Related substances & organisms	-

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Dow AgroSciences Hokko Chemical Co.
Example products using this active	Mimic Confirm Romdan
UK LERAP status	No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details	-

ENVIRONMENTAL FATE
for tebufenozide

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		0.83	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		23800	A5 - Ethyl acetate	-
		74800	A5 - Acetone	-
		130000	A5 - Methanol	-
		3200	A5 - Toluene	-
Melting point (oC)		191	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		200	A5 - start temp.	-
Flashpoint (oC)		-	-	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.78 X 1004	Calculated	-
	Log P	4.25	A5	High
Bulk density (g ml-1)/Specific gravity		1.03	A5	-
Dissociation constant (pKa) at 25oC		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 20oC (mPa)		1.56 X 10-04	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		6.59 X 10-05	A5	Non-volatile
GUS leaching potential index		1.76	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	5.15 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
Maximum UV-vis absorption L mol-1 cm-1		Methanol: 235nm = 16331; [Acidic methanol: 233nm = 16458; [Basic methanol: 235nm = 15844	A5	-
Surface tension (mN m-1)		71.6	A5	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	400	W3	Very persistent
	DT50 (lab at 20oC)	26.2	A5	Non-persistent
	DT50 (field)	24.2	A5	Non-persistent
	DT90 (lab at 20oC)	-	-	-
	DT90 (field)	-	-	-
	DT50 modelling endpoint	-	-	-
	Note	EU dossier lab studies DT50 range 20.8-31.2 days, field studies DT50 range 10.2-81.7 days; Other sources: 348 days (DW4), 105-704 (Q3)
Dissipation rate RL50 on plant matrix	Value	37.7	R4	-
	Note	Published literature RL50 range 3.0-69.5 days, 3 field grown crops, various matrices, n=6
Dissipation rate RL50 on and in plant matrix	Value	38.5	R4	-
	Note	Published literature RL50 range 3.5-58.7 days, 3 field grown crops, various matrices, n=3
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5	-
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	-
Water-sediment DT50 (days)		145.4	A5	Slow
Water phase only DT50 (days)		12.6	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	5.73	A5	Slightly mobile
	Kfoc	572
	1/n	1.005
	Notes and range	EU dossier kf range 1.616-8.208 mL/g, kfoc range 351-894 mL/g, 1/n range 0.943-1.138, Soils=5
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
4-(N'-(3,5-dimethylbenzoyl_-N-(1,1-dimethylethyl)hydrazinocarbonyl)benzoic acid (Ref: RH-2651)		Soil	0.200	Major fraction, Relevancy unknown
4-(N'-(3,5-dimethylbenzoyl-N-(1,1-dimethylethyl)hydrazinocarbonyl)phenyl acetic acid (Ref: RH-2703)		Soil	0.08	Minor fraction, Relevancy unknown
N-(1,1-dimethyethyl)-N-(4-acetylebenzoyl)-3,5-dimethylbenzohydrazine (Ref: RH-6595)		Soil	0.088	Minor fraction, Relevancy unknown

ECOTOXICOLOGY
for tebufenozide

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	70	A5 Whole fish	Low potential
	CT50 (days)	2		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	5.5	L2 Rat, 2 year	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		> 2150	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		-	-	-
Fish - Acute 96 hour LC50 (mg l-1)		3.0	A5 Lepomis macrochirus	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		0.71	A5 Pimephales promelas	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		3.8	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.029	A5 Daphnia magna	Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		0.82	F3 Americamysis bahia	Moderate
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		> 2400	A4 Unknown species Vegetative vigour, NOEL as g/ha	-
		> 2400	A4 Unknown species Seedling emergence, NOEL as g/ha	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.23	A5 Scenedemus subspicatus	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 234	A5	Low
	Oral acute 48 hour LD50 (μg bee-1)	> 100	A4	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 1000	A5 Eisenia foetida	Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		> 1000	A5 Eisenia foetida	Low
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	730	R4 Folsomia candida, NOEC: 9 mg kg-1	-
Other arthropod (1)	LR50 g ha-1	432.0	> A5 Aphidius rhopalosiphi, adults	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	165.4	A5 Typhlodromus pyri, protonymph	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: Unknown, 28days	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for tebufenozide

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	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 4.3	A5 Rat, 4 hr (whole body)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.02	A5 Dog, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.008	A5 Dog, SF=100	-
Dermal penetration studies (%)		0.2-2.1	A5 concentration dependent	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Acceptable for proposed uses
	Occupational	Possible risk to operators particularly in orchards - PPE/PPC advised Acceptable risk to other farm workers
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		Liver and kidney toxicant Known to be It is hemotoxic causing red blood cell damage

: 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: R51, R53
EC Safety Classification		S61
WHO Classification		U	-	Unlikely to present an acute hazard
US EPA Classification (formulation)		III	-	Caution - Slightly toxic
UN Number		-
Waste disposal & packaging		-

TRANSLATIONS
for tebufenozide

Language	Name
English	tebufenozide
French	tebufenozide
German	Tebufenozid
Danish	tebufenozid
Italian	tebufenozide
Spanish	tebufenozid; tebufenocida
Greek	-
Slovenian	tebufenozid
Polish	tebufenozyd
Swedish	-
Hungarian	-
Dutch	-

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Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk