clethodim (Ref: RE 45601) ** cletodime ** Translations

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GENERAL INFORMATION

Description: A herbicide used to control annual and perennial grasses for use on sugarbeet

Introduction: 1987, first reported

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

Status	Annex 1
Dossier rapporteur/co-rapporteur	Netherlands
Date inclusion expires	31/05/2021

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia, USA

General status:

Pesticide type	Herbicide
Substance group	Cyclohexanedione
Substance origin	Synthetic
Mode of action	Selective, systemic. An acetyl CoA carboxylase inhibitor (ACCase).
CAS RN	99129-21-2
EC number	-
CIPAC number	508
US EPA chemical code	121011
Chiral molecule	Yes
Chemical formula	C17H26ClNO3S
SMILES	O=C1/C(C(=O)CC(CC(SCC)C)C1)=C(\NOCC=CCl)CC
International Chemical Identifier (InChI)	InChI=1/C17H26ClNO3S/c1-4-14(19-22-8-6-7-18)17-15(20)10-13(11-16(17)21)9-12(3)23-5-2/h6-7,12-13,20H,4-5,8-11H2,1-3H3/b7-6?,19-14+
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	359.92
IUPAC Name	(5RS)-2-{(E)-1-[(2E)-3-chloroallyloxyimino]propyl}-5-[(2RS)-2-(ethylthio)propyl]-3-hydroxycyclohex-2-en-1-one
CAS Name	2-[(1E)-1-[[[(2E)-3-chloro-2-propenyl]oxy]imino]propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one
Other status information	-
Herbicide Resistance Classification (HRAC)	A
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Physical state	Viscous amber to green-yellow coloured liquid depending upon purity
Related substances & organisms	-

Formulations:

Property	Value
Example manufacturers of products using this active	Arysta LifeSciences FRANCE Agan Chemicals Loveland Products
Example products using this active	Select 12 SC Select 240 Centurion
UK LERAP status	No UK approval for use or outside scope
Formulation and application details	Usually available as an emulsifiable concentrate that is mixed with water and used as a spray.

ENVIRONMENTAL FATE

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		5450	A5	High
Solubility - In organic solvents at 20oC (mg l-1)		100000	A5 - Xylene	-
		100000	A5 - Methanol	-
		900000	A5 - Acetone	-
		900000	A5 - Ethyl acetate	-
Melting Point (oC)		-80	A5	-
Boiling Point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		100.5	A5	-
Flashpoint (oC)		-	-	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.38 X 1004	Calculated	-
	Log P	4.14	A5	High
Bulk density (g ml-1)/Specific gravity		1.16	A5	-
Dissociation constant (pKa) at 25oC		4.47	A5	-
		Note: Weak acid
Vapour pressure at 25oC (mPa)		2.08 X 10-03	A5	Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1)		1.4 X 10-07	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		2.68 X 10-10	Q2	Non-volatile
GUS leaching potential index		-0.69	Calculated	Low leachability
SCI-GROW groundwater index (µg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	6.26 X 10-04	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution: 256nm = 13183, 203nm = 13490; [Acidic solution: 258nm = 12882, 207nm = 12589; [Basic solution: 210nm = ??, 282nm = 21878	A5	-
Surface tension (mN m-1)		52.9	A5 at 21oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	0.55	A5	Non-persistent
	DT50 (lab at 20oC)	0.55	A5	Non-persistent
	DT50 (field)	3	Y4	Non-persistent
	DT90 (lab at 20oC)	2.61	A5	-
	DT90 (field)	-	-	-
	Note	EU dossier lab studies DT50 range 0.17-3.04 days, DT90 range 0.76-8.50 days; Other studies: DT50 1-3 days (R3)
Aqueous photolysis DT50 (days) at pH 7	Value	5.45	A4 - @ 25degC	Moderately fast
	Note	pH sensitive: DT50 1.6 @ pH 5, 7.79 @ pH 9 all @ 25 degC
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	Very persistent
	Note	pH sensitive: DT50 41 days at pH 5, stable pH 7 and pH 9 all at 25 degC
Water-Sediment DT50 (days)		16.7	A4	Fast
Water phase only DT50 (days)		7.0	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	0.39	A5	Mobile
	Kfoc	22.7
	1/n	1.01
	Notes and range	EU dossier Kf range 0.065-0.112, Kfoc range 2.71-43.17, 1/n range 0.97-1.04, Soils=3
pH sensitivity		Yes

Key metabolites:

Metabolite		Formation Medium	Estimated Maximum Occurrence Fraction	91/414 Relevancy
clethodim sulfoxide		Soil	0.730	Major fraction, Relevant
clethodim sulfone		Soil	0.16	Major fraction, Relevant
clethodim oxazole sulfone		Soil	0.100	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation Medium / Rate	Estimated Maximum Occurrence Fraction	Metabolising Enzymes
-	clethodim imine ketone	Water (Photolysis)	-	-
-	clethodim isoxazole	Soil (Anaerobic)	-	-
-	clethodim oxazole sulfoxide	Water (Photolysis); Soil (Aerobic)	-	-
-	clethodim oxazole	Soil (Aerobic)	-	-
-	clethodim imine sulfoxide	Soil (Aerobic)	-	-
-	3-chloropropenal	Water (Photolysis)	-	-
-	clethodim oxazole sulfide	Water (Photolysis)	-	-
-	clethodim trione sulfoxide	Water (Photolysis)	-	-
-	clethodim chloroallyl alcohol	Water (Photolysis)	-	-

ECOTOXICOLOGY

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	2.1	A5 Whole fish	Low potential
	CT50 (days)	4.9		-
Bioaccumulation potential		-	Calculated	Low
Mammals - Acute oral LD50 (mg kg-1)		1133	A5 Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg-1)	30	Z2 Rat	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		> 1640	A5 Colinus virginianus	Moderate
Birds - Short term dietary (LC50/LD50)		> 851 mg kg bw-1 day-1	A5 Anas platyrhynchos	-
Fish - Acute 96 hour LC50 (mg l-1)		25	A5 Salmo gairdneri	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		3.9	A5 Oncorhynchus mykiss	-
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		> 100	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		49	A5 Daphnia magna	-
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)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		-	-	-
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		1.9	A5 Lemna gibba	Moderate
Algae - Acute 72 hour EC50, growth (mg l-1)		> 12.0	A5 Pseudokirchneriella subcapitata	Low
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees - Acute 48 hour LD50 (µg bee-1)		> 43	A5 Oral	Moderate
Earthworms - Acute 14 day LC50 (mg kg-1)		454	L3	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	240	240A5 Aphidius rhopalosiphi	Moderately harmful at 1 kg ha-1
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	9.6	A5 Typhlodromus pyri	Moderately harmful at 1 kg ha-1
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant effect Carbon mineralisation: No significant effect	A5 Dose: 2.7 mg/kg, effects may be significant at higher doses	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Mammals - Acute oral LD50 (mg kg-1)		1133	A5 Rat	Moderate
Mammals - Dermal LD50 (mg kg-1 body weight)		> 4167	A5 Rabbit	-
Mammals - Inhalation LC50 (mg l-1)		< 3.25	A5 Rat, 4hr (whole body)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.16	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.20	A2 Dog, SF=100	-
Dermal penetration studies (%)		15-42	A5 concentration dependant	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Acceptable risk for proposed uses
	Occupational	Acceptable risk for proposed uses
Examples of European MRLs (mg kg-1)	Value	-
	Note	For the EU pesticides database click here
Drinking Water MAC (µg l-1)		0.1	EU Dir 89/778/EC limit; A5 Calc MAC=25.0 µg/l	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
General human health issues		Moderately toxic Possible liver and blood toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		Not explosive or oxiding
CLP classification 2013		-
EC Risk Classification		Xn - Harmful: R22
EC Safety Classification		-
WHO Classification		NL	-	Not listed
US EPA Classification (formulation)		III	-	Caution - Slightly toxic
UN Number		-
Waste disposal & packaging		-

TRANSLATIONS