hexazinone

hexazinone (Ref: DPX A3674)
** DPX-3674 ** Translations

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GENERAL INFORMATION
for hexazinone

Description: A herbicide used to control many annual, biennial and perennial weeds, as well as some woody plants

Introduction: 1975, USA

EC Regulation 1107/2009 (repealing 91/414): 0 cellpadding= 5 cellspacing= 1 width= 99% > valign= top bgcolor= #E2E2E2 > Status valign= top bgcolor= #E2E2E2 > Not approved valign= top bgcolor= #E2E2E2 > Dossier rapporteur/co-rapporteur valign= top bgcolor= #E2E2E2 > - valign= top bgcolor= #E2E2E2 > Date inclusion expires valign= top bgcolor= #E2E2E2 > Essential use only > Approved for use () or known to be used () in the following European countries: 0 cellpadding= 5 cellspacing= 1 width= 99% > bgcolor= #E2E2E2 >

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> Also registered in: Australia

General status:

Pesticide type Herbicide

Substance group Triazinone

Substance origin Synthetic
Mode of action Non-selective with contact action, absorbed through the roots and foliage of plants. Inhibits photosynthesis (photosystem II).

CAS RN 51235-04-2

EC number 257-074-4

CIPAC number 374

US EPA chemical code 107201

Chiral molecule No

Chemical formula C₁₂H₂₀N₄O₂

SMILES O=C1/N=C(\N(C(=O)N1C2CCCCC2)C)N(C)C

International Chemical Identifier key (InChIKey) CAWXEEYDBZRFPE-UHFFFAOYSA-N

International Chemical Identifier (InChI) InChI=1S/C12H20N4O2/c1-14(2)10-13-11(17)16(12(18)15(10)3)9-7-5-4-6-8-9/h9H,4-8H2,1-3H3

Structure diagram/image available? Yes

Molecular mass (g mol^-1) 252.31

PIN (Preferred Identification Name) -

IUPAC name 3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

CAS name 3-cyclohexyl-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

Other status information Potential groundwater contaminant; Chemical subject to PIC regulations

Herbicide Resistance Classification (HRAC) C1

Herbicide Resistance Classification (WSSA) 5

Insecticide Resistance Classification (IRAC) Not applicable

Fungicide Resistance Classification (FRAC) Not applicable

Physical state Colourless crystals

Related substances & organisms
diuron

sulfometuron-methyl

Formulations:

Property Value
Example manufacturers & suppliers of products using this active
DuPont
AgroCare
Makhteshim Agan Group
FCC Ltd

Example products using this active
Velpar Weed Killer
Pronone
Fertihexa
Elinone

UK LERAP status No UK approval for use or outside scope

Formulation and application details Available in a variety of formulations including wettable granules, suspension concentrates and tablets.

ENVIRONMENTAL FATE
for hexazinone

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20^oC (mg l^-1)		33000	K4	High
Solubility - In organic solvents at 20^oC (mg l^-1)		626000	C4 - Acetone	-
		334000	C4 - Toluene	-
		2146500	C4 - Methanol	-
		837000	C4 - Benzene	-
Melting point (^oC)		113.5	L3	-
Boiling point (^oC)		Decomposes on distillation	L2	-
Degradation point (^oC)		-	-	-
Flashpoint (^oC)		-	-	-
Octanol-water partition coefficient at pH 7, 20^oC	P	1.48 X 10⁰¹	Calculated	-
Octanol-water partition coefficient at pH 7, 20^oC	Log P	1.17	P4	Low
Bulk density (g ml^-1)/Specific gravity		1.25	L3	-
Dissociation constant (pKa) at 25^oC		2.2	L3	-
Dissociation constant (pKa) at 25^oC		Note: Weak base
Vapour pressure at 25^oC (mPa)		0.03	G4	Non-volatile
Henry's law constant at 25^oC (Pa m³ mol^-1)		1.10 X 10^-07	H4	Non-volatile
Henry's law constant at 20^oC (dimensionless)		8.30 X 10^-11	K3	Non-volatile
GUS leaching potential index		4.58	Calculated	High leachability
SCI-GROW groundwater index (μg l^-1) for a 1 kg ha^-1 or 1 l ha^-1 application rate	Value	2.15 X 10⁺⁰⁰	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
Maximum UV-vis absorption L mol^-1 cm^-1		-	-	-
Surface tension (mN m^-1)		-	-	-

Degradation:

Property Value Source/Quality Score/Other Information Interpretation

Soil degradation (days) (aerobic) DT50 (typical) 105 L3 Persistent

DT50 (lab at 20^oC) 90 F3 Moderately persistent

DT50 (field) - - -

DT90 (lab at 20^oC) - - -

DT90 (field) - - -

Note Other sources: DT50 30 (sand) - 180 (clay) days (R3); General literature DT50 range 59-64 days (R3)

Aqueous photolysis DT50 (days) at pH 7 Value 56 K4 Stable

Note -

Aqueous hydrolysis DT50 (days) at 20^oC and pH 7 Value 56 K4 Moderately persistent

Note -

Water-sediment DT50 (days) - - -

Water phase only DT50 (days) - - -

Soil adsorption and mobility:

Property Value Source/Quality Score/Other Information Interpretation

Linear K_d - G3 Mobile

K_oc 54

Notes and range Other sources: Koc 610 (P3)

Freundlich K_f - - -

K_foc -

¹/_n -

Notes and range -

pH sensitivity -

Key metabolites:

Metabolite Formation medium Estimated maximum occurrence fraction 91/414 relevancy

3-(4-hydroxycyclohexyl)-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)dione Soil -

3-cyclohexyl-6-(methylamino)-1-methyl-1,3,5-triazine-2,4-(1H,3H)-dione Soil Major

3-(4-hydroxycyclohexyl)-6-(methylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione Soil Major

ECOTOXICOLOGY
for hexazinone

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	7	P4	Low potential
Bio-concentration factor	CT₅₀ (days)	Not available	P4	-
Bioaccumulation potential		-	Calculated	Low
Mammals - Acute oral LD₅₀ (mg kg^-1)		1690	G4 Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg^-1)	-	L2 Rat, 2 year	-
Mammals - Short term dietary NOEL	(ppm diet)	> 200	L2 Rat, 2 year	-
Birds - Acute LD₅₀ (mg kg^-1)		> 2258	G4 Colinus virginianus	Low
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l^-1)		> 320	G4 Oncorhynchus mykiss	Low
Fish - Chronic 21 day NOEC (mg l^-1)		-	-	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l^-1)		> 85	J4 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l^-1)		> 50	F3 Daphnia magna, LOEC	-
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)		> 0.072	F2 Lemna minor, 7 day	Moderate
Algae - Acute 72 hour EC₅₀, growth (mg l^-1)		0.0145	F4 Pseudokirchneriella subcapitata	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l^-1)		-	-	-
Honeybees	Contact acute 48 hour LD₅₀ (μg bee^-1)	-	-	-
	Oral acute 48 hour LD₅₀ (μg bee^-1)	-	-	-
	Unknown mode acute 48 hour LD₅₀ (μg bee^-1)	60	L2	Moderate
Earthworms - Acute 14 day LC₅₀ (mg kg^-1)		-	-	-
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	-	-	-
Other arthropod (1)	% Effect	-	-	-
Other arthropod (2)	LR₅₀ g ha^-1	-	-	-
Other arthropod (2)	% Effect	-	-	-
Soil micro-organisms		-	-	-
Mesocosm study data	NOEAEC mg l^-1	-	-	-
Mesocosm study data	NOEAEC mg l^-1	-	-	-

HUMAN HEALTH AND PROTECTION
for hexazinone

General:

Property Value Source/Quality Score/Other Information Interpretation

Mammals - Acute oral LD₅₀ (mg kg^-1) 1690 G4 Rat Moderate

Mammals - Dermal LD50 (mg kg^-1 body weight) > 5000 L3 Rabbit -

Mammals - Inhalation LC50 (mg l^-1) 7.48 L3 Rat -

Other Mammal toxicity endpoints - -

ADI - Acceptable Daily Intake (mg kg^-1bw day^-1) 0.05 L3 -

ARfD - Acute Reference Dose (mg kg^-1bw day^-1) - - -

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg^-1bw day^-1) - - -

Dermal penetration studies (%) - - -

Dangerous Substances Directive 76/464 - - -

Exposure Limits - - -

Exposure Routes Public -

Occupational -

Examples of European MRLs (mg kg^-1) Value -

Note For the EU pesticides database click here

Drinking Water MAC (μg l^-1) - - -

Health issues:

Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

-

General human health issues Highly toxic

: 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 No information available

CLP classification 2013 -

EC Risk Classification Xn - Harmful: R22
Xi - Irritant: R36
N - Dangerous for the environment: R50, R53

EC Safety Classification S2, S60, S61

WHO Classification II - Moderately hazardous

US EPA Classification (formulation) II - Warning - Moderately toxic

UN Number -

Waste disposal & packaging -

TRANSLATIONS
for hexazinone

Language	Name
English	hexazinone
French	hexazinone
German	Hexazinon
Danish	hexazinon
Italian	esazinone
Spanish	hexazinona
Greek	-
Slovenian	heksazinon
Polish	heksazynon
Swedish	-
Hungarian	hexazinone
Dutch	-

Record last updated: Wednesday 14 January 2015
Contact: aeru@herts.ac.uk

Pesticide type	Herbicide
Substance group	Triazinone
Substance origin	Synthetic
Mode of action	Non-selective with contact action, absorbed through the roots and foliage of plants. Inhibits photosynthesis (photosystem II).
CAS RN	51235-04-2
EC number	257-074-4
CIPAC number	374
US EPA chemical code	107201
Chiral molecule	No
Chemical formula	C₁₂H₂₀N₄O₂
SMILES	O=C1/N=C(\N(C(=O)N1C2CCCCC2)C)N(C)C
International Chemical Identifier key (InChIKey)	CAWXEEYDBZRFPE-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C12H20N4O2/c1-14(2)10-13-11(17)16(12(18)15(10)3)9-7-5-4-6-8-9/h9H,4-8H2,1-3H3
Structure diagram/image available?	Yes
Molecular mass (g mol^-1)	252.31
PIN (Preferred Identification Name)	-
IUPAC name	3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione
CAS name	3-cyclohexyl-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione
Other status information	Potential groundwater contaminant; Chemical subject to PIC regulations
Herbicide Resistance Classification (HRAC)	C1
Herbicide Resistance Classification (WSSA)	5
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Physical state	Colourless crystals
Related substances & organisms	diuron sulfometuron-methyl

Property	Value
Example manufacturers & suppliers of products using this active	DuPont AgroCare Makhteshim Agan Group FCC Ltd
Example products using this active	Velpar Weed Killer Pronone Fertihexa Elinone
UK LERAP status	No UK approval for use or outside scope
Formulation and application details	Available in a variety of formulations including wettable granules, suspension concentrates and tablets.

Metabolite	Formation medium	Estimated maximum occurrence fraction	91/414 relevancy
3-(4-hydroxycyclohexyl)-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)dione	Soil		-
3-cyclohexyl-6-(methylamino)-1-methyl-1,3,5-triazine-2,4-(1H,3H)-dione	Soil		Major
3-(4-hydroxycyclohexyl)-6-(methylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione	Soil		Major

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
		-				-
General human health issues		Highly toxic