Cyhexatin (Ref: OMS 3029)	Last updated: 25/09/2024
(Also known as: tricyclohexyltin hydroxide; ENT 27395-X)

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SUMMARY

Cyhexatin is an acaricide used mainly on fruit crops. It has a low water solubility and is non-volatile. It is moderately persistent in soil systems. The risk of it leaching to groundwater, based on its physico-chemical properties, is low. Cyhexatin tends to be highly toxic to most biodiversity. It is moderately toxic to mammals if ingested.

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 High alert: Potential for particle bound transport: High	Ecotoxicity High alert: Fish acute ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description	An acaricide used to control mites on a variety of crops. Can also be a pesticide transformation product
Example pests controlled	European red mite; Citrus mite; Two-spotted spider mite
Example applications	Fruit including apples, pears, citrus, peaches, plums, nectarines, strawberries; Ornamentals; Hops; Almonds; Walnuts
Efficacy & activity	-
Availability status	-
Introduction & key dates	circa 1970, introduced

GB regulatory status

GB COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
GB LERAP status	No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status	Not approved
Dossier rapporteur/co-rapporteur	Italy
Date EC 1107/2009 inclusion expires	Expired
EU Candidate for substitution (CfS)	Not applicable
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	C₁₈H₃₄OSn
Canonical SMILES	C1CCC(CC1)[Sn](C2CCCCC2)C3CCCCC3.O
Isomeric SMILES	-
International Chemical Identifier key (InChIKey)	WCMMILVIRZAPLE-UHFFFAOYSA-M
International Chemical Identifier (InChI)	InChI=1S/3C6H11.H2O.Sn/c3*1-2-4-6-5-3-1;;/h3*1H,2-6H2;1H2;/q;;;;+1/p-1/rC18H34OSn/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-19H,1-15H2
2D structure diagram/image available?	Yes

General status

Pesticide type	Insecticide, Acaricide, Metabolite
Metabolite Type	Soil
Substance groups	Organotin insecticide; Organotin acaricide; Organometal insecticide; Organometal acaricide
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Non-systemic with contact action, acts by inhibiting oxidative phosphorylation. Inhibitor of mitochondrial ATP synthase.
CAS RN	13121-70-5
EC number	236-049-1
CIPAC number	289
US EPA chemical code	101601
PubChem CID	6327054
CLP index number	050-002-00-0
Molecular mass	385.17
PIN (Preferred Identification Name)	tricyclohexylstannanol
IUPAC name	tricyclohexyltin hydroxide
CAS name	tricyclohexylhydroxystannane
Other status information	OSPAR soc; Severe Marine Pollutant; Chemical subject to PIC regulations
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Class (HRAC MoA class)	Not applicable
Herbicide Resistance Class (WSSA MoA class)	Not applicable
Insecticide Resistance Class (IRAC MoA class)	12B
Fungicide Resistance Class (FRAC MOA class)	Not applicable
Examples of recorded resistance	Panonychus ulmi, Tetranychus mcdanieli, Tetranychus urticae, Tetranychus kanzawai, Tetranychus pacificus
Physical state	Solid

Can be a metabolite of:

Parent	Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
azocyclotin	Soil	-	-

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Chemia SPA ITALY Cerexagri Oxon Italia SpA Dow Chemicals
Example products using this active	Citran 500 SC Plictran Aracnol F
Formulation and application details	Usually supplied as a suspension concentrate or wettable powder.

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		1.0	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)		216000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Chloroform	-
		37000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Methanol	-
		16000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Benzene	-
		10000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Toluene	-
Melting point (°C)		-	-	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	6.92 X 1004	Calculated	-
	Log P	4.84	C4 C = AGRITOX dataset. Dataset is no longer available. 4 = Verified data	High
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		-	-	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		1.15 X 10-03	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source at 25 °C	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		2.00 X 10-02	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Non-volatile
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
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)	50	H4 H = The US ARS pesticide properties database. Dataset is no longer available. 4 = Verified data	Moderately persistent
	DT₅₀ (lab at 20 °C)	50	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source	Moderately persistent
	DT₅₀ (field)	50	F3 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 ) 3 = Unverified data of known source	Moderately persistent
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	Best available data
Dissipation rate RL₅₀ (days) on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ (days) on and in plant matrix	Value	-	-	-
	Note	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	-	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
	Note	Degraded by UV light
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	Stable	C4 C = AGRITOX dataset. Dataset is no longer available. 4 = Verified data	Stable
	Note	-
Water-sediment DT₅₀ (days)		-	-	-
Water phase only DT₅₀ (days)		-	-	-
Sediment phase only DT₅₀ (days)		-	-	-
Air degradation		As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀		-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd (mL g⁻¹)	-	H3 H = The US ARS pesticide properties database. Dataset is no longer available. 3 = Unverified data of known source	Non-mobile
	Koc (mL g⁻¹)	4365
	Notes and range	Best available data
Freundlich	Kf (mL g⁻¹)	-	-	-
	Kfoc (mL g⁻¹)	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		0.61	Calculated	Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	1.18 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		High	Calculated	-
Potential for loss via drain flow		Non-mobile	Calculated	-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk		-	-	-
Bio-concentration factor	BCF (l kg⁻¹)	10000	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source Estimated	High potential
	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)		265	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 Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg⁻¹)	1	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Rat 2 yr	High
	(ppm diet)	-		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		520	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)	32	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Apis mellifera	Moderate
	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	-	-	-
	Notes	-
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)		Moderately harmful	AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005 2 = Unverified data of unknown source Typhlodromus pyri	-
Beneficial insects (Ground beetles)		-	-	-

Aquatic ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		0.06	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Perciformes spp.	High
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		0.0002	C3 C = AGRITOX dataset. Dataset is no longer available. 3 = Unverified data of known source Daphnia magna	High
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		-	-	-
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)		0.00032	F3 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 ) 3 = Unverified data of known source Americamysis bahia	High
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)		0.000018	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 Scenedesmus subspicatus	High
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-
Marine bivalves		-	-	-

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)		265	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 Rat	Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		2000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rabbit	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		-	-	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		0.003	A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		0.02	A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes	-
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 I; 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 A3 A = Chromosome aberration (EFSA database) 3 = Negative ; 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 ?Possibly, status not identified XNo, known not to cause a problem XNo, known not to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser XNo, known not to cause a problem XNo, known not to cause a problem No data found Eye irritant Phototoxicant   ✓Yes, known to cause a problem No data found
General human health issues		Highly toxic

Handling issues

Property	Value and interpretation
General	IMDG Transport Hazard Class 6.1
CLP classification 2013	Health: H302, H312, H332 Environment: H400, H410
WHO Classification	II (Moderately hazardous)
UN Number	UN2786
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	cyhexatin
French	cyhexatin
German	Cyhexatin
Danish	cyhexatin
Italian	ciexatin
Spanish	cihexatin
Greek	-
Polish	cyheksatyna
Swedish	-
Hungarian	cyhexatin
Dutch	cyhexatin
Norwegian	-

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Record last updated:	25/09/2024
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