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Nitenpyram (Ref: CGA 246916)
Last updated: 24/07/2024
(Also known as: (E)-nitenpyram ; TI 204; niterndipoine)
GENERAL INFORMATION
Description
A systemic insecticide used mainly to kill external parasites in livestock and domestic pets
Availability status
Current
Introduction & key dates
1989 discovered, 1995 launched
Examples of veterinary uses
Mainly used to treat adult flea infestations in mammals and maggot infestations on reptiles as off-label
Examples of species treated
Cats; Dogs; Reptiles
Approval status
VMR 2013/2033 approval status (GB/UK)
Approved
EU Regulatory approval status
Approved
Chemical structure
Isomerism
Isomeric - molecule has one E/Z centre
Chemical formula
C₁₁H₁₅ClN₄O₂
Canonical SMILES
CCN(CC1=CN=C(C=C1)Cl)C(=C[N+](=O)[O-])NC
Isomeric SMILES
CCN(CC1=CN=C(C=C1)Cl)/C(=C/[N+](=O)[O-])/NC
International Chemical Identifier key (InChIKey)
CFRPSFYHXJZSBI-DHZHZOJOSA-N
International Chemical Identifier (InChI)
InChI=1S/C11H15ClN4O2/c1-3-15(11(13-2)8-16(17)18)7-9-4-5-10(12)14-6-9/h4-6,8,13H,3,7H2,1-2H3/b11-8+
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
nitenpyram -
General status
Veterinary substance type
Insecticide, Antiparasitic
Substance groups
Neonicotinoid insecticide
Minimum active substance purity
>98%
Known relevant impurities
-
Substance origin
Semi-synthetic
Mode of action
Systemic with translaminar activity, stomach and contact action affecting insects nervous system. No long term activity. Nicotinic acetylcholine receptor (nAChR) channel blocker.
Molecular targets
[Nicotinic acetylcholine receptors, Binder]
CAS RN
150824-47-8
EC number
634-900-5
CIPAC number
None allocated
US EPA chemical code
-
PubChem CID
3034287
CLP index number
No data found
Therapeutic Class
Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents
ATCvet Code
QP53BX02
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
270.72
PIN (Preferred Identification Name)
(1E)-N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-N'-methyl-2-nitroethene-1,1-diamine
IUPAC name
(E)-N-(6-chloro-3-pyridylmethyl)-N-ethyl-N'-methyl-2-nitrovinylidenediamine
CAS name
(1E)-N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N'-methyl-2-nitro-1,1-ethenediamine
Other status information
PAN listed Highly Hazardous Chemical
Relevant Environmental Water Quality Standards
-
Physical state
Pale yellow to orange crystalline solid
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Bob Martin Flea Tablets Elanco Europe Ltd UK National authorisation (IC) Authorised veterinary medicine for general sale (AVM-GSL)
Capstar 11.4mg Tablets for Cats and Small Dogs Elanco Europe Ltd GB National authorisation Authorised veterinary medicine for general sale (AVM-GSL)
Johnsons 4Fleas 57mg Tables for Dogs Elanco Europe Ltd UK National authorisation (IC) Authorised veterinary medicine for general sale (AVM-GSL)
Formulation and application details
Usually supplied in tablet form for oral administration
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
570000
E4 E = Manufacturers safety data sheets
4 = Verified data
 High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
1000000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Methanol		 -
700000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Chloroform		 -
290000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone		 -
4500
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Xylene		 -
Melting point (°C)
72
E4 E = Manufacturers safety data sheets
4 = Verified data
 -
Boiling point (°C)
417.2
E4 E = Manufacturers safety data sheets
4 = Verified data
 -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
2.19 X 10-01 Calculated -
Log P
-0.66
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
at 25 °C		 Low
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.254
E4 E = Manufacturers safety data sheets
4 = Verified data
 -
Dissociation constant pKa) at 25 °C
3.1
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
-
Vapour pressure at 20 °C (mPa)
0.0011
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
3.54 X 10-13
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)
- - -
Refractive Index
- - -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
8
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
General literature states DT₅₀ 1-15 days
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Stable
Note
Stable pH 3-7 at 25 °C; pH9 DT₅₀ = 2.9 days
Water-sediment DT₅₀ (days)
- - -
Water 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)
-
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
 Mobile
Koc (mL g⁻¹)
60
Notes and range
Estimated
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
2.01 Calculated Transition state
Bio-concentration factor
BCF (l kg⁻¹)
Low risk
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Based on LogP < 3		 Low risk
CT₅₀ (days)
- -
Known soil and groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
2-(N-(6-chloro-3-pyridylmethyl)-N-ethyl-N-methylformamidine 3-CPMF Plant -
2-(N-(6-chloro-3-pyridylmethyl)-N-ethyl)amino-2-methyliminoacetic acid 2-CPMA Plant -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
1575
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
1124
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Anas platyrhynchos		 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)
32.2
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Moderate
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)
- - -
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)
0.138
R4 R = Peer reviewed scientific publications
4 = Verified data
 High
Chronic
- - -
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) as Mortality, Contact LC₅₀ ppm
> 0.33
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
Chrysoperla carnea Larva		 -
Beneficial insects (Parasitic wasps)
- - -
Beneficial insects (Predatory mites)
- - -
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)
10
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Oncorhynchus mykiss		 Moderate
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)
10000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Daphnia magna		 Low
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)
- - -
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)
26
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Pseudokirchneriella subcapitata		 Low
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)
1575
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
5.8
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
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
- - -
Exposure Routes
Public
-
Occupational
-
Mammalian dose elimination route and rate
In mammals it is excreted mostly unchanged in the urine
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
No data found
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
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
XNo, known not to cause a problem
 No data found No data found
Respiratory tract irritant Skin irritant Skin sensitiser
✓Yes, known 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
No further information available
Handling issues
Property
Value and interpretation
General
Corrosive
CLP classification 2013
Health: H302, H315, H319, H335
Environment: H400, H410
WHO Classification
II (Moderately hazardous)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
Limited shelf-life. Store at -20 DegC
TRANSLATIONS
Language
Name
English
nitenpyram
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 24/07/2024
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