Cyromazine (Ref: OMS 2014)

Cyromazine (Ref: OMS 2014)	Last updated: 12/01/2021
(Also known as: CGA 72662; cyclopropylmelamine ; cyromazinum; AI3-52713)

SUMMARY

Cyromazine is an insecticide no longer approved for use in the EU. It is highly soluble in water and considered relatively volatile. Its persistence in soil and water systems is highly dependant on local conditions. Cyromazine has a low mammalian toxicity but may cause adverse effects on reproduction and development if ingested and is also a skin irritant. It is moderately toxic to birds, fish, aquatic invertebrates and earthworms but less so to honeybees.

GENERAL INFORMATION

Description

An insect larvicide used mainly to control Diptera larvae and flies on livestock and other insect pests in the field and greenhouse

Example pests controlled

Leafminers; Colorado beetle; Fungas gnats; Sciarid flies; Shore flies

Example applications

Vegetables including cabbage, onions, beans, lentils, peppers, turnips; Lupins; Curcubits; Tomatoes; Potatoes

Efficacy & activity

Availability status

Current

Introduction & key dates

1980, 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

Spain/Italy

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

Australia, USA

Chemical structure

Isomerism

Chemical formula

C₆H₁₀N₆

Canonical SMILES

C1CC1NC2=NC(=NC(=N2)N)N

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

LVQDKIWDGQRHTE-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C6H10N6/c7-4-10-5(8)12-6(11-4)9-3-1-2-3/h3H,1-2H2,(H5,7,8,9,10,11,12)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
cyromazine	-

General status

Pesticide type

Insecticide, Veterinary substance

Substance group

Triazine

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Contact action, interfering with moulting and pupation. Chitin synthesiser.

CAS RN

66215-27-8

EC number

266-257-8

CIPAC number

420

US EPA chemical code

121301

PubChem CID

47866

Molecular mass

166.18

PIN (Preferred Identification Name)

N1-cyclopropyl-1,3,5-triazine-2,4,6-triamine

IUPAC name

N-cyclopropyl-1,3,5-triazine-2,4,6-triamine

CAS name

N-cyclopropyl-1,3,5-triazine-2,4,6-triamine

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Drosophila melanogaster, Liriomyza trifolii, Lucilia cuprina, Musca domestica

Physical state

White powder

Formulations

Property

Value

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

Trigard
Larvadex

Example products using this active

Syngenta
Novartis Animal Health

Formulation and application details

Often supplied as a wettable powder that is mixed with water and used as a pour-on

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

13000

High

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

1400

Acetone

210

Dichloromethane

100

Hexane

17000

Methanol

Melting point (°C)

223.2

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

223.2

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.17 X 10⁰⁰

Calculated

Log P

0.069

Low

Bulk density (g ml⁻¹)

1.35

Dissociation constant pKa) at 25 °C

5.22

Weak base

Vapour pressure at 20 °C (mPa)

4.48 X 10^-04

Low volatility

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

5.80 X 10^-09

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral solution: 208nm = 39070
Acidic solution: 215.5nm = 29540, 241.3nm = 17340
Basic solution: 230nm = 11540

Surface tension (mN m⁻¹)

59.0

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

31.8

Moderately persistent

DT₅₀ (field)

9.7

Non-persistent

DT₉₀ (lab at 20 °C)

101

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range: 1.8-56 days, DT₉₀ range 9.6-186 days, field studies DT₅₀ range 2.3 (Switzerland) - 17 (France) days; Other sources: 150 days (DW4)

Dissipation rate RL₅₀ on plant matrix

Value

14.3

Note

Cucumber fruit, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

17.7

Note

Green bean, whole plant, hydroponics system, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable pH 5 to pH 9 at temperatures between 30 and 70 °C

Water-sediment DT₅₀ (days)

228

Slow

Water phase only DT₅₀ (days)

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

7.62

Moderately mobile

K_foc

409

¹/_n

0.81

Notes and range

EU dossier K_f range 0.52-50.38 mL g⁻¹, K_foc range 40.2-1784 mL g⁻¹, ¹/_n range 0.714-0.92, Soils=11

pH sensitivity

Yes

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.37

Calculated

Low leachability

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

Value

1.89 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

melamine (Ref: CGA 235129)

Soil

0.745

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

1-methyl-cyromazine

Rat; Plant

Ref: NOA 435343

carboxylic acid of cyromazine

Soil (Aerobic)

0.107

hydroxy-cyromazine

Animal

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

3387

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

300

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 1785

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1370 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 100

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 1

Oncorhynchus mykiss

Moderate

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

> 100

Daphnia magna

Low

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

4.6

Daphnia magna

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

> 120

Chironomus riparius

Low

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.025

Chironomus riparius whole system

Moderate

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)

124

Scenedemus subspicatus

Low

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

> 100

Unknown species

Low

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 200

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

186

Apis mellifera

Low

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)

> 1.3

Bombus terrestris 77d as LC₅₀

Moderate

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)

> 1000

Eisenia foetida

Low

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

333

Eisenia foetida 56 days

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

891

>, EC₅₀ reproduction
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

Typhlodromus pyri

% Effect

Soil micro-organisms

[Microbial soil respiration and nitrification: NOEC=100 mg kg⁻¹]

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)

3387

Rat

Low

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

3100

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.6

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.06

Dog SF=100

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

0.1

Rabbit SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

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

0.06

Dog SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk to bystanders

Occupational

No unacceptable risks to operators or other workers identified

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

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Hgh dose can cause nausea, vomiting, abdominal distress and diarrhoea

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H315, H319, H373, H335
Environment: H411

EC Risk Classification

Xn - Harmful: R20/22
Xi - Irritant: R36/37/38

EC Safety Classification

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

cyromazine

French

cyromazine

German

Cyromazin

Danish

cyromazin

Italian

ciromazina

Spanish

ciromazina

Greek

Polish

cyromazyna

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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