cyromazine (Ref: OMS 2014) ** CGA 72662 ** cyclopropylmelamine ** cyromazinum ** AI3-52713 ** Translations

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SUMMARY

Cyromazine is an insecticide approved for use in the EU and in other countries. 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
for cyromazine

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

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

Status	Approved
Dossier rapporteur/co-rapporteur	Spain/Italy
Date inclusion expires	31/12/2019
EU Candidate for substitution (CfS)	No
Listed in EU database	Yes

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

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

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
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 (g mol-1)	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)	17
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Drosophila melanogaster Liriomyza trifolii Lucilia cuprina Musca domestica
Physical state	White powder
Related substances & organisms	-

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Syngenta Novartis Animal Health
Example products using this active	Trigard Larvadex
UK LERAP status	No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details	Often supplied as a wettable powder that is mixed with water and used as a pour-on.

ENVIRONMENTAL FATE
for cyromazine

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		13000	A5	High
Solubility - In organic solvents at 20oC (mg l-1)		1400	A5 - Acetone	-
		210	A5 - Dichloromethane	-
		100	A5 - Hexane	-
		17000	A5 - Methanol	-
Melting point (oC)		223.2	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		223.2	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.17 X 1000	Calculated	-
	Log P	0.069	A5	Low
Bulk density (g ml-1)/Specific gravity		1.35	B5	-
Dissociation constant (pKa) at 25oC		5.22	A5	-
		Note: Weak base
Vapour pressure at 20oC (mPa)		4.48 X 10-04	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		5.80 X 10-09	A5	Non-volatile
GUS leaching potential index		2.09	Calculated	Transition state
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	8.21 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
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	A5	-
Surface tension (mN m-1)		59.0	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	93	K4	Moderately persistent
	DT50 (lab at 20oC)	31.8	A5	Moderately persistent
	DT50 (field)	9.7	A3	Non-persistent
	DT90 (lab at 20oC)	101	A5	-
	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	R3	-
	Note	Cucumber fruit, n=1
Dissipation rate RL50 on and in plant matrix	Value	17.7	R3	-
	Note	Green bean, whole plant, hydroponics system, n=1
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5 -	-
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Stable pH 5 to pH 9 at temperatures between 30 and 70 degC
Water-sediment DT50 (days)		228	A5	Slow
Water phase only DT50 (days)		15	A5	Slow

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	7.62	A5	Moderately mobile
	Kfoc	409
	1/n	0.81
	Notes and range	EU dossier Kf range 0.52-50.38 mL/g, Kfoc range 40.2-1784 mL/g, 1/n range 0.714-0.92, Soils=11
pH sensitivity		Yes

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	-	-
-	hydroxy-cyromazine	Animal	-	-
(Ref: NOA 435343)	carboxylic acid of cyromazine	Soil (Aerobic)	0.107	-

ECOTOXICOLOGY
for cyromazine

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	1	A5	Low potential
	CT50 (days)	Not available		-
Mammals - Acute oral LD50 (mg kg-1)		3387	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	15	B5 Rat	High
	(ppm diet)	300		-
Birds - Acute LD50 (mg kg-1)		> 1785	A5 Colinus virginianus	Moderate
Birds - Short term dietary (LC50/LD50)		> 1370 mg kg bw-1 day-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		> 100	A5 Oncorhynchus mykiss	Low
Fish - Chronic 21 day NOEC (mg l-1)		> 1	A5 Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		> 100	A5 Daphnia magna	Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		4.6	A5 Daphnia magna	Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		> 120	A5 Chironomus riparius	Low
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1)		0.025	A4 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	A5 Scenedemus subspicatus	Low
Algae - Chronic 96 hour NOEC, growth (mg l-1)		> 100	Q1 Unknown species	Low
Honeybees (Apis spp.)	Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	> 200	A5 Apis mellifera	Low
	Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	186	A5	Low
	Unknown mode acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	A5 Apis mellifera	-	Low
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	R3 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	A5 Eisenia foetida	Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		333	A5 Eisenia foetida, 56 days	Low
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	891	>, EC50 reproduction A5 Aphidius rhopalosiphi	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	47	A5 Typhlodromus pyri	-
	% Effect	-	-	-
Soil micro-organisms		[Microbial soil respiration and nitrification: NOEC=100 mg kg-1]	A5	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for cyromazine

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		3387	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 3100	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 3.6	A5 Rat, 4 hr (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.06	A5 Dog, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.1	A5 Rabbit, SF=100	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.06	A5 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
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Genotoxic	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	A3; B3; C3; D0; E0	-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
		-		-
General human health issues		Hgh dose can cause nausea, vomiting, abdominal distress and diarrhoea
Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative			Key: Other : Yes, known to cause a problem : No, known not to cause a problem : Possibly, status not identified - : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		Not explosive or oxidising
CLP classification 2013		Health: H315, H319, 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
for cyromazine

Language	Name
English	cyromazine
French	cyromazine
German	Cyromazin
Danish	cyromazin
Italian	ciromazina
Spanish	ciromazina
Greek	-
Slovenian	ciromazin
Polish	cyromazyna
Swedish	-
Hungarian	-
Dutch	-

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Record last updated: Saturday 29 June 2019
Contact: aeru@herts.ac.uk