Dinitramine (Ref: USB 3584)	Last updated: 02/09/2023
(Also known as: diethamine)

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SUMMARY

Dinitramine is a soil incorporated pre-plant herbicide. It has a low aqueous solubility and a low volatility. Depending on local conditions it may be moderately persistent in soils. Based on its physico-chemical properties it is not expected to leach to groundwater. Available ecotoxicological data is very limited but dinitramine is moderately toxic to birds and fish. Dinitramine has a low oral mammalian toxicity.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Moderately persistent; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate Warning: Significant data are missing	Human health Low alert Warning: Significant data are missing

GENERAL INFORMATION

Description	A soil incorporated pre-plant herbicide used to control many annual grasses and broad-leaved weeds
Example pests controlled	Crab grass; Barnyard grass; Couch grass
Example applications	Peas; Soybeans; Cotton; Sunflowers; Tomatoes; Rice; Legumes
Efficacy & activity	-
Availability status	-
Introduction & key dates	1973, USA

UK regulatory status

UK COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
UK LERAP status	No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status	Not approved
Dossier rapporteur/co-rapporteur	Not applicable
Date EC 1107/2009 inclusion expires	Expired
EU Candidate for substitution (CfS)	-
Listed in EU database	Yes
Approved for use (✓) under EC 1107/2009 in the following EU Member States	ATAustria BEBelgium BGBulgaria CYCyprus CZCzech Republic DEGermany DKDenmark EEEstonia ELGreece                   ESSpain FIFinland FRFrance HRCroatia HUHungary IEIreland ITItaly LTLithuania LULuxembourg                   LVLatvia MTMalta NLNetherlands PLPoland PTPortugal RORomania SESweden SISlovenia SKSlovakia
Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries	ISIceland NONorway

Additional information

Also used in	-

Chemical structure

Isomerism	None
Chemical formula	C₁₁H₁₃F₃N₄O₄
Canonical SMILES	CCN(CC)C1=C(C=C(C(=C1[N+](=O)[O-])N)C(F)(F)F)[N+](=O)[O-]
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	OFDYMSKSGFSLLM-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C11H13F3N4O4/c1-3-16(4-2)9-7(17(19)20)5-6(11(12,13)14)8(15)10(9)18(21)22/h5H,3-4,15H2,1-2H3
2D structure diagram/image available?	Yes

General status

Pesticide type	Herbicide
Substance groups	Dinitroaniline herbicide; Phenylenediamine herbicide
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Selective, absorbed by roots and shoots. Microtubule assembly inhibition.
CAS RN	29091-05-2
EC number	249-419-2
CIPAC number	None allocated
US EPA chemical code	102301
PubChem CID	34468
CLP index number	No data found
Molecular mass	322.24
PIN (Preferred Identification Name)	N1,N1-diethyl-2,6-dinitro-4-(trifluoromethyl)benzene-1,3-diamine
IUPAC name	N1,N1-diethyl-2,6-dinitro-4-trifluoromethyl-m-phenylenediamine
CAS name	N3,N3-diethyl-2,4-dinitro-6-(trifluoromethyl)-1,3-benzenediamine
Other status information	-
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Class (HRAC MoA class)	K1
Herbicide Resistance Class (WSSA MoA class)	3
Insecticide Resistance Class (IRAC MoA class)	Not applicable
Fungicide Resistance Class (FRAC MOA class)	Not applicable
Examples of recorded resistance	-
Physical state	Yellow crystals

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Wacker-Chemie Velsicol
Example products using this active	Cobex
Formulation and application details	Usually formulated as an emulsifiable concentrate

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		1.1	H4 H = The US ARS pesticide properties database. Dataset is no longer available. 4 = Verified data	Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)		1040000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Acetone	-
		473000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Benzene	-
		227000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Xylene	-
		6700	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source n-Hexane	-
Melting point (°C)		98.5	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Boiling point (°C)		-	-	-
Degradation point (°C)		200	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Flashpoint (°C)		30.5	R4 R = Peer reviewed scientific publications 4 = Verified data	-
Octanol-water partition coefficient at pH 7, 20 °C	P	2.00 X 1004	Calculated	-
	Log P	4.3	H4 H = The US ARS pesticide properties database. Dataset is no longer available. 4 = Verified data	High
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		1.47	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		0.479	H4 H = The US ARS pesticide properties database. Dataset is no longer available. 4 = Verified data	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		1.40 X 10-01	H4 H = The US ARS pesticide properties database. Dataset is no longer available. 4 = Verified data	Moderately volatile
Maximum UV-vis absorption L mol⁻¹ cm⁻¹		-	-	-
Surface tension (mN m⁻¹)		-	-	-

Degradation

Property		Value	Source; quality score; and other information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT₅₀ (typical)	38	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Moderately persistent
	DT₅₀ (lab at 20 °C)	30	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source	Moderately persistent
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	Best available data
Dissipation rate RL₅₀ on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ on and in plant matrix	Value	-	-	-
	Note	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	-	-	-
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	-	-	-
	Note	-
Water-sediment DT₅₀ (days)		-	-	-
Water phase only DT₅₀ (days)		-	-	-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	H3 H = The US ARS pesticide properties database. Dataset is no longer available. 3 = Unverified data of known source	Non-mobile
	Koc	4000
	Notes and range	Best available data
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		0.59	Calculated	Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	1.12 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		Medium	Calculated	-
Potential for loss via drain flow		Non-mobile	Calculated	-
Bio-concentration factor	BCF (l kg⁻¹)	235	J4 J = Pesticide Action Network database (click here ) 4 = Verified data	Threshold for concern
	CT₅₀ (days)	Not available		-

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 3000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	Low
Mammals - Short term dietary NOEL	(mg kg⁻¹)	-	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
	(ppm diet)	2000		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		1200	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Colinus virginianus	Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		-	-	-
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Soil micro-organisms		-	-	-
Collembola	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Non-target plants		-	-	-
		-	-	-
Honeybees (Apis spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Chronic	-	-	-
Bumblebees (Bombus spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
		-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
		-
Mason bees (Osmia spp.)	Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
Other bee species (1)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Other bee species (2)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Beneficial insects (Ladybirds)		-	-	-
Beneficial insects (Lacewings)		-	-	-
Beneficial insects (Parasitic wasps)		-	-	-
Beneficial insects (Predatory mites)		-	-	-
Beneficial insects (Ground beetles)		-	-	-

Aquatic ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		0.753	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		-	-	-
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
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)		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		-	-	-
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-

HUMAN HEALTH AND PROTECTION

General

Property		Value	Source; quality score; and other information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 3000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		6800	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		0.16	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		-	-	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		-	-	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)		-	-	-
Dermal penetration studies (%)		-	-	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Routes	Public	-
	Occupational	-
MRLs	European	EU MRL pesticide database
	Great Britain	GB MRL Register
	Notes	-
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-
Mammalian dose elimination route and rate		-	-	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor No data found A0 A = Chromosome aberration (EFSA database) 0 = No data ; B0 B = DNA damage/repair (EFSA database) 0 = No data ; C0 C = Gene mutation (EFSA database) 0 = No data ; D0 D = Genome mutation (EFSA database) 0 = No data ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant No data found XNo, known not to cause a problem No data found Respiratory tract irritant Skin irritant Skin sensitiser No data found No data found No data found Eye irritant Phototoxicant   No data found No data found
General human health issues		No further information available

Handling issues

Property	Value and interpretation
General	No information available
CLP classification 2013	Health: H312 Environment: H400, H410
WHO Classification	III (Slightly hazardous)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	dinitramine
French	dinitramine
German	Dinitramin
Danish	dinitramin
Italian	dinitramina
Spanish	dinitramina
Greek	-
Polish	dinitramina
Swedish	-
Hungarian	-
Dutch	-
Norwegian	-

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Record last updated:	02/09/2023
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242