pymetrozine (Ref: CGA 215944) ** pimetrozin ** Translations

Environmental Fate - Ecotoxicology - Human Health

GENERAL INFORMATION

Description: A novel azomethine insecticide suitable for use in integrated crop management to control aphids, whitefiles and other pests

Introduction: 1992, first reported; 1993, first introduced

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

Status	Annex 1
Dossier rapporteur/co-rapporteur	Germany
Date inclusion expires	31/12/2015

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia

General status:

Pesticide type	Insecticide
Substance group	Pyridine
Substance origin	Synthetic
Mode of action	Selective, neural inhibition of feeding behavior that eventually starves insect.
CAS RN	123312-89-0
EC number	-
CIPAC number	593
US EPA chemical code	101103
Chemical formula	C10H11N5O
SMILES	O=C2N(/N=C/c1cccnc1)C\C(=N/N2)C
International Chemical Identifier (InChI)	InChI=1/C10H11N5O/c1-8-7-15(10(16)14-13-8)12-6-9-3-2-4-11-5-9/h2-6H,7H2,1H3,(H,14,16)/b12-6+
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	217.23
IUPAC Name	(E)-4,5-dihydro-6-methyl-4-(3-pyridylmethyleneamino)-1,2,4-triazin-3(2H)-one
CAS Name	4,5-dihydro-6-methyl-4-[(E)-(3-pyridinylmethylene)amino]-1,2,4-triazin-3(2H)-one
Other status information	-
Herbicide Resistance Classification (HRAC)	Not applicable
Insecticide Resistance Classification (IRAC)	9B
Fungicide Resistance Classification (FRAC)	Not applicable
Physical state	Colourless to brown coloured crystals
Related substances & organisms	silica

Formulations:

Property	Value
Example manufacturers of products using this active	Syngenta
Example products using this active	Chess Plenum Endeavour Fulfill
UK LERAP status	None
Formulation and application details	Often supplied as wettable granules that are mixed with water and used as a spray.

ENVIRONMENTAL FATE

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		270	A5	Moderate
Solubility - In organic solvents at 20oC (mg l-1)		1	A5 - n-Hexane	-
		34	A5 - Toluene	-
		94	A5 - Acetone	-
		1200	A5 - Ethyl acetate	-
Melting Point (oC)		Decomposes before melting	A5	-
Boiling Point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		190	A5	-
Flashpoint (oC)		Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	6.46 X 10-01	Calculated	-
	Log P	-0.19	A5	Low
Bulk density (g ml-1)/Specific gravity		1.37	A5	-
Dissociation constant (pKa) at 25oC		4.06	A5	-
		Note: Weak acid
Vapour pressure at 25oC (mPa)		4.20 X 10-03	A5	Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1)		3.00 X 10-06	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		1.36 X 10-09	Q2	Non-volatile
GUS leaching potential index		0.94	Calculated	Low leachability
SCI-GROW groundwater index (µg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.54 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
Maximum UV-vis absorption L mol-1 cm-1		299.2nm = 20500	A5	-
Surface tension (mN m-1)		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	14	A5	Non-persistent
	DT50 (lab at 20oC)	12.5	A5	Non-persistent
	DT50 (field)	35.5	A5	Moderately persistent
	DT90 (lab at 20oC)	32	A5	-
	DT90 (field)	185	A5	-
	Note	EU dossier lab studies DT50 range 2-23 days, DT90 range 20-122 days, field studies DT50 range 2-69 days, n=7, DT90 range = 55-288 days
Aqueous photolysis DT50 (days) at pH 7	Value	6.8	A5	Moderately fast
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	Very persistent
	Note	DT50: 8.6 days at pH 5, stable pH 7 and pH 9, all at 25 deg C
Water-Sediment DT50 (days)		83	A5	Moderately fast
Water phase only DT50 (days)		6	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	18.0	A5	Slightly mobile
	Koc	1510
	Notes and range	EU dossier Kd range 3.06-47.6 mL/g, Koc range 246-7875 mL/g, Soils=10
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		No

Key metabolites:

Metabolite		Formation Medium	Estimated Maximum Occurrence Fraction	91/414 Relevancy
4,5-dihydro-5-hydroxy-6-methyl-4-[3-pyridinylmethylene)amino]-1,2,4-triazine-3-(2H)-one (Ref: CGA 359009)		Soil	0.540	Major fraction, Relevant
Ref: CGA 363430		Soil	0.100	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation Medium / Rate	Estimated Maximum Occurrence Fraction	Metabolising Enzymes
(Ref: CGA 180777)	-	Soil (a = Aerobic, b = Anaerobic)	a=0.170; b=0.850	-
(Ref: CGA 215525)	-	Water (Hydrolysis)	0.480	-
(Ref: CGA 249257)	-	a = Soil (Anaerobic); b = Water (Photolysis)	a=0.130; b=0.210	-
(Ref: CGA 294849)	-	Soil (Aerobic)	0.130	-
(Ref: CGA 300407)	-	Water (Hydrolysis)	0.630	-
(Ref: CGA 363431)	-	Soil (Aerobic)	0.240	-
(Ref: GS 23199)	-	Soil (Anaerobic)	0.150	-

ECOTOXICOLOGY

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	-	A5 Low risk	-
	CT50 (days)	Not available		-
Bioaccumulation potential		-	Calculated	Low
Mammals - Acute oral LD50 (mg kg-1)		5820	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	3.7	L2 Rat, 2 year	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		> 2000	A5 Anas platyrhynchos	Moderate
Birds - Short term dietary (LC50/LD50)		> 5200 mg kg feed-1	A5 Anas platyrhynchos	-
Fish - Acute 96 hour LC50 (mg l-1)		> 100	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		> 11.7	A5 Oncorhynchus mykiss	-
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		87	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.025	A5 Daphnia magna	-
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		61.7	E4 Americamysis bahia EC50	Moderate
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1)		0.313	A5 Chironomus riparius	Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		-	-	-
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		106	E4 Lemna gibba	Low
Algae - Acute 72 hour EC50, growth (mg l-1)		21.6	A4 Raphidocelis subcapitata, 72 hour	Low
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees - Acute 48 hour LD50 (µg bee-1)		> 117	A5 Oral	Low
Earthworms - Acute 14 day LC50 (mg kg-1)		> 250	A5 Eisenia foetida	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		1.39	A5 Eisenia foetida	Moderate
Other soil macro-organisms - e.g. Collembola	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	95.2	Beneficial capacity Dose: 0.6 kg ha-1 A5 Aphidius colemani, adult	Harmful
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	17.4	Beneficial capacity Dose: 0.6 kg ha-1 A5 Typhlodromus pyri, lifecycle	Harmless
Soil micro-organisms		Nitrogen mineralisation: No significant effect Carbon mineralisation: No significant effect	A5 Dose: 6.66 mg/kg soil	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Mammals - Acute oral LD50 (mg kg-1)		5820	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		1.8	A5 Rat	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.03	A5 Dog, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.1	A5 Rabbit, SF=100	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.03	A5 Rat, 90 day, SF=100	-
Dermal penetration studies (%)		6.0	A5	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	[No unacceptable risks to bystanders identified]
	Occupational	[No unacceptable risks to operators or other workers identified]
Examples of European MRLs (mg kg-1)	Value	Blackberries and raspberries: 3.0; Lettuce: 2.0; Sweet peppers and legume vegetables: 1.0; Cucumbers summer squash, eggplants, tomatoes and strawberries: 0.5; Melons (not watermelons), pumpkins and winter squash: 0.2; Cabbages, apricots, nectaries and peaches: 0.05; Other vegetables, other fruit and cereal grains: 0.02
	Note	[Current May 2007.] For the EU pesticides database click here
Drinking Water MAC (µg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
	-	-			-
General human health issues		[May affect most major organs at high doses], [Highly toxic - harmful if swallowed]

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		[Not explosive or oxidising], [Non-flammable and is combustible]
EC Risk Classification		[Carcinogen category 3: R40], [N - Dangerous for the environment: R52, R53]
EC Safety Classification		S2, S36/37, S61
WHO Classification		NL	-	Not listed
US EPA Classification (formulation)		III	-	Caution - Slightly toxic
UN Number		-
Waste disposal & packaging		-

TRANSLATIONS