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GET ADDITIONAL DATA HERE!

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

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for pymetrozine

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

Example pests controlled: Pollen beetles; Aphids; Whiteflies

Example applications: OSR; Potatoes; Brassicas; Spinach; Cucumbers; Ornamentals

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1992, first reported; 1993, first introduced

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Germany/Belgium
Date inclusion expires 30/06/2019
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

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

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism Isomeric
Chemical formula C10H11N5O
Canonical SMILES CC1=NNC(=O)N(C1)N=CC2=CN=CC=C2
Isomeric SMILES CC1=NNC(=O)N(C1)/N=C/C2=CN=CC=C2
International Chemical Identifier key (InChIKey) QHMTXANCGGJZRX-WUXMJOGZSA-N
International Chemical Identifier (InChI) InChI=1S/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+
2D structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Insecticide
Substance group Pyridine
Minimum active substance purity 970 g/kg
Known relevant impurities EU dossier - None declared
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
PubChem CID 9576037
Molecular mass (g mol-1) 217.23
PIN (Preferred Identification Name) -
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 -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) 9B
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance Bemisia tabaci
Physical state White to light brown coloured crystals
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • 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

for pymetrozine

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 270 A5 - @ 25 degC Moderate
Solubility - In organic solvents at 20oC (mg l-1) 1000 A5 - n-Hexane -
34000 A5 - Toluene -
940000 A5 - Acetone -
260000 A5 - Ethyl acetate -
Melting point (oC) Decomposes before melting A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 217 A5 -
Flashpoint (oC) Not expected to self ignite; 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 20oC (mPa) 4.20 X 10-03 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 3.00 X 10-06 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 0.65 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 3.14 X 10-03 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 246nm=9500, 299.2nm = 20500 A5 -
Surface tension (mN m-1) 68.4 A5 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 5 A5 Non-persistent
DT50 (lab at 20oC) 4.6 A5 Non-persistent
DT50 (field) 22.6 A5 Non-persistent
DT90 (lab at 20oC) 32 A5 -
DT90 (field) 320.7 A5 -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 range 2.05-29.2 days, DT90 range 8.3-96.9 days, field studies DT50 range 3.81-183 days, n=8, DT90 range 65.2 - >1000 days
Dissipation rate RL50 on plant matrix Value 2.5 R3 -
Note Lettuce head, n=1
Dissipation rate RL50 on and in plant matrix Value 2.5 R4 -
Note Published literature RL50 range 0.9-4.2 days,4 field crops, various matrices, n=4
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 -
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 Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 19.3 A5 Slightly mobile
Kfoc 1049
1/n 0.880
Notes and range EU dossier 2014 Kf range 3.10-47.7 mL/g, kfoc range 246-3080, 1/n range 0.790-0.952, Soils=7
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
5-hydroxy-6-methyl-4-(((E)-pyridin-3-ylmethylene)amino)-4,5-dihydro-1,2,4-triazin-3(2H)-one (Ref: CGA 359009) This metabolite may cause environmental pollution, click here for further information Soil   0.537   Major fraction, Relevant
6-methyl-4-((6-oxo-1,6-dihydropyridine-3-ylmethylene)-amino)4,5-dihydro-2H-(1,2,4)triazin-3,5-dione (Ref: CGA 363430) This metabolite may cause environmental pollution, click here for further information Soil   0.100   Major fraction, Relevant
5-hydroxy-6-methyl-4-(((E)-(6-oxo-1,6-dihydropyridin-3-yl)methylene)amino)-4,5-dihydro-1,2,4-triazin-3(2H)-one (Ref: CGA 363431) This metabolite may cause environmental pollution, click here for further information Soil   0.238   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
pyridin-3-ylmethanol
(Ref: CGA 128632)
- Plant - -
nicotinic acid
(Ref: CGA 180777)
- Soil (a = Aerobic, b = Anaerobic) a=0.170; b=0.850 -
4-amino-6-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one
(Ref: CGA 215525)
- Water (Hydrolysis) 0.480 -
6-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one
(Ref: CGA 249257)
- a = Soil (Anaerobic); b = Water (Photolysis) a=0.130; b=0.210 -
6-oxo-1,6-dihydropyridine-3-carbaldehyde
(Ref: CGA 255548)
- a=Soil; b=Groundwater a=0.137 -
3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid
(Ref: CGA 266591)
- Plant - -
4-amino-6-methyl-1,2,4-triazine-3,5(2H,4H)-dione
(Ref: CGA 294849)
- Soil (Aerobic) 0.130 -
nicotinaldehyde
(Ref: CGA 300407)
- Water (Hydrolysis) 0.630 -
4,6-dimethyl-1,2,4-triazine-3,5(2H,4H)-dione
(Ref: CGA 371075)
- a=Soil; b=Groundwater a=0.008 -
6-methyl-1,2,4-triazine-3,5(2H,4H)-dione
(Ref: GS 23199)
- Soil (Anaerobic) 0.150 -
6-methylene-3-oxo-5,6-dihydro-1,2,4-triazin-4(3H)-aminium
(Ref: SYN 505866)
- a=Soil; Groundwater a=0.007 -
6-methyl-4-{[(E)-(6-oxo-1,6-dihydropyridin-3-yl)methylene]amino}-1,2,4-triazine-3,5(2H,4H)-dione
(Ref: SYN 510306)
- a=Soil; b=Groundwater a=0.006 -


ECOTOXICOLOGY

for pymetrozine

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) Low risk A5 Based on LogP < 3 Low potential
CT50 (days) - -
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 Low
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 Low
Fish - Chronic 21 day NOEC (mg l-1) > 11.7 A5 Oncorhynchus mykiss Low
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 Moderate
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
Non-target plants - - -
- - -
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 Contact acute 48 hour LD50 (μg bee-1) > 200 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 117 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
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 LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect 95.2 Beneficial capacity
Dose: 0.6 kg ha-1
A5 Aphidius coleman, adult
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 17.4 Beneficial capacity
Dose: 0.6 kg ha-1
A5 Typhlodromus pyri, lifecycle
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 6.66 mg kg-1 soil
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for pymetrozine

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
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 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.03 A5 Rat, 90 day, SF=100 -
Dermal penetration studies (%) 0.05-5% A5 concentration dependent -
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
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues May affect most major organs at high doses
Highly toxic - harmful if swallowed
USEPA - probable human carcinogen

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

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
Non-flammable but is combustible
CLP classification 2013 Health: H351, H361f, H361d
Environment: H412
EC Risk Classification Click here to view information omn the EU risk phrases Carcinogen category 3: R40
Reproduction risk category 3: R62, R63
N - Dangerous for the environment: R52, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S36/37, S61
WHO Classification NL - Not listed
US EPA Classification (formulation) III - Caution - Slightly toxic
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for pymetrozine

Language Name
English pymetrozine
French pymetrozine
German Pymetrozin
Danish pymetrozin
Italian pymetrozine
Spanish pimetrozina
Greek pymetrozine
Slovenian pimetrozin
Polish pymetrozyna
Swedish pymetrozin
Hungarian pimetrozin
Dutch pymetrozine

Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk