Aziprotryne (Ref: C 7019)

Aziprotryne (Ref: C 7019)	Last updated: 04/01/2021
(Also known as: aziprotryn; mesanoril; aziprotyne)

SUMMARY

Aziprotryne is a herbicide that is not approved for use in the EU and is considered obsolete. It is moderately soluble in water, volatile and not expected to leach to groundwater. Little is known about its environmental persistence. Data suggests it is not highly toxic and is not expected to bioaccumulate. It is not highly toxic to birds and is considered moderately toxic to fish.

GENERAL INFORMATION

Description

An obsolete herbicide once used as a post-emergence treatment for the control of broad-leaved weeds

Example pests controlled

Lambsquarter; Crab grass; Foxtail; Chickweed; Ragweed; Pigrass; Witchgrass; Wild oats; Couch; Black grass

Example applications

Vegetables including Brussel sprouts, cabbage, kale, onions, peas; Lettuce; Sorghum; Sunflower

Efficacy & activity

Availability status

Obsolete

Introduction & key dates

1967, first reported

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

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

Also used in

Chemical structure

Isomerism

Chemical formula

C₇H₁₁N₇S

Canonical SMILES

CC(C)NC1=NC(=NC(=N1)N=[N+]=[N-])SC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

AFIIBUOYKYSPKB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C7H11N7S/c1-4(2)9-5-10-6(13-14-8)12-7(11-5)15-3/h4H,1-3H3,(H,9,10,11,12)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Triazine

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Photosynthetic electron transport inhibitor, selective with residual activity, absorbed through roots and foliage

CAS RN

4658-28-0

EC number

225-101-9

CIPAC number

326

US EPA chemical code

263301

PubChem CID

3032472

Molecular mass

225.27

PIN (Preferred Identification Name)

4-azido-6-(methylsulfanyl)-N-(propan-2-yl)-1,3,5-triazin-2-amine

IUPAC name

4-azido-N-isopropyl-6-methylthio-1,3,5-triazin-2-amine

CAS name

4-azido-N-(1-methylethyl)-6-(methylthio)-1,3,5-triazin-2-amine

Other status information

Phototoxic to cauliflower

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Colourless crystalline solid

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Brasoran
Mesoranil

Example products using this active

Novartis
Ciba Geigy

Formulation and application details

Usually supplied as a wettable powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

at 25 °C

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

27000

Acetone

37000

Dichloromethane

1200

Ethyl acetate

400

Benzene

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

100

Octanol-water partition coefficient at pH 7, 20 °C

1.00 X 10⁰³

Calculated

Log P

Moderate

Bulk density (g ml⁻¹)

1.40

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.267

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

1.09 X 10^-03

Non-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)

Non-persistent

DT₅₀ (lab at 20 °C)

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

K_d

Moderately mobile

K_oc

294

Notes and range

Estimated

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.07

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

3.89 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 3000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 4000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 1.0

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 26

Daphnia magna

Moderate

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)

Non-target plants

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

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)

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 pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

1.0

Allolobophora caliginosa as LOEL

High

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

Mesocosm study data

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

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

3000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.21

Rat 4 hr

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

Exposure Routes

Public

Occupational

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Not classified: Obsolete

EC Risk Classification

Not classified: Obsolete

EC Safety Classification

Not classified: Obsolete

WHO Classification

O (Obsolete substance)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

aziprotryne

French

aziprotryne

German

Aziprotryn

Danish

aziprotryn

Italian

aziprotrina

Spanish

aziprotrina

Greek

Polish

azyprotryna

Swedish

Hungarian

Dutch

Record last updated:	04/01/2021
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