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Chemical Identification
Common Name
Acetamiprid
中文通用名
啶虫脒
IUPAC
(E)-N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1-methylacetamidine
CAS
(E)-N-[(6-chloro-3-pyridinyl)methyl]-N'-cyano-N-methylethanimidamide
CAS No.
135410-20-7
Molecular Formula
C10H11ClN4
Molecular Structure
Category
Activity
Insecticide.
Acetamiprid is a systemic insecticide suitable for application to foliage, seeds and soil. It has ovicidal and larvicidal activity against Hemiptera and Lepidoptera and controls adults of Thysanoptera. It is active principally by ingestion although some contact action is also observed; penetration through the cuticle, however, is low. The product has translaminar activity, allowing improved control of aphids and whiteflies on the underside of leaves and provides residual activity lasting up to four weeks. Acetamiprid demonstrates ovicidal activity against organophosphate-resistant tobacco budworms and multi-resistant Colorado beetles.


Acetamiprid acts at the nicotinic acetylcholine receptor on the postsynaptic membrane of insect nerve cells. The product shows a high affinity for the insect binding site and a much lower affinity for the vertebrate site, allowing a good margin of selective toxicity to insects. Acetamiprid is not metabolised by acetylcholinesterase thus causing uninterrupted nerve signal transmission. Insects demonstrate symptoms of poisoning within 30 minutes of treatment, showing excitement and then paralysis prior to death.

In field trials, acetamiprid (at lower application rates) gave equal or better control of pests than established products. Nippon Soda reports that the product does not leave any residual stain or odour on tea leaves.

For the product Assail, a maximum of five applications per season, not more than once very seven days, is recommended for leafy vegetables and cole crops. A maximum of four applications per season, no more than once every 7 days, is recommended for fruiting vegetables and pome fruits. For grapes, a maximum of two applications per season, no more than once every 14 days, is recommended. A preharvest interval of 7 days is advised. For Chipco Tristar, a maximum five applications per year is recommended for outdoor ornamentals and two applications per year for ornamentals grown in shadehouses, lathhouses and greenhouses at a minimum spray interval of once every 7 days. Direct spraying to upper and lower leaf surfaces and stems, up to a maximum of five applications per season with a 7 day preharvest interval, is advised for Pristine RTU.

To explore the possibility of acetamiprid as a preventative termicide, the toxic and repellent activity of acetamiprid against Reticulitermes was determined in the laboratory (IPPC, 2004). The action of acetamiprid was slow and mortality reached 100% in 4 days after treatment in the soil treated by 4 mg/L of acetamiprid solution. Acetamiprid had strong repellent and toxic activities on the termites.
CropUse
Crop uses:
apples, aubergines, brassicas, cabbages, canola, cereals, citrus, cole crops, cotton, cucumbers, flowering plants, fruiting vegetables, grapes, leafy vegetables, lettuce, melons, noncrop uses, onions, ornamentals, palm fruit, peaches, peppers, pome fruits, potatoes, rice, stone fruits, strawberries, sugar beet, tea, tobacco, tomatoes, vines, water melon


Sugar beet

50 g ai/ha

Fruit

0.05-0.1 g ai/hl

Cotton

12.5-100 g ai/ha

Tobacco

100 g ai/ha

Citrus

6-10 g ai/hl

Ornamentals and flowering plants

28-112 g ai/1000L

Leafy and fruiting vegetables, cole crops, pome fruits, grapes

28- 168 g ai/ha

Leafy and fruiting vegetables, cole crops, pome fruits, grapes

 

Pest Spectrum
Control Sucking-Type Insects: Hemiptera, Lepidoptera and controls adults of Thysanoptera, aphids and whiteflies, organophosphate-resistant tobacco budworms and multi-resistant Colorado beetles.
Formulation
DP = Dustable powder
GR = Granule
SP = Soluble powder
SL = Soluble concentrate
SC = Suspension concentrate (=flowable concentrate)
WG = Water dispersible granules
WP = Wettable p
Premix
Flonicamid+Acetamiprid
Fenitrothion+Acetamiprid
Chlorantraniliprole+Acetamiprid
Acetamiprid+triazophos
Acetamiprid+thiosultap-monosodium
Acetamiprid+Thiocyclam
Acetamiprid+phoxim
Acetamiprid+lambda-cyhalothrin
Acetamiprid+emamectin benzoate
Acetamiprid+diazinon
Acetamiprid+cypermethrin
Acetamiprid+chlorpyrifos
Acetamiprid+carbosulfan
Acetamiprid+bifenthrin
Acetamiprid+beta-cypermethrin
acetamiprid+alpha-cypermethrin
Abamectin+acetamiprid
Physical Properties
White crystalline solid.Molecular weight:222.7 g/mol.Melting point 98.9℃.Vapor pressure <1 × 10-6 Pa. Soluble in acetone, acetonitrile, methanol, dichloromethane.
Toxicology
(Rat): Acute oral LD50 417 mg/kg (male); 314 mg/kg (female)
Environmental Profile
Ecotoxicology:
Fish: LC50 (48 h) >100 mg/l (carp).
WATER SOLUBILITY:?4250 mg/l at 25.

Carp [96 h]

LC50 >100 mg/L

Daphnia [48 h]

LC50 49.8 mg/L

Honey bee [contact, 48 h]

LD50 8.09 μg/L moderately toxic

Honey bee [oral, 48 h]

LD50 14.53 μg/L moderately toxic

Mallard duck [14 d]

LD50 84 mg/kg moderately toxic

Rainbow trout [96 h]

LC50 >100 mg/L practically nontoxic

Bluegill sunfish [96 h]

LC50 >119.3 mg/L practically nontoxic

Fathead minnow [96 h]

LC5095.8 mg/L slightly toxic

Blue-green alga

EC50 >1.3 mg/L

Green alga

EC50>1.2 mg/L

Freshwater diatom

EC50>1.1 mg/L

Duckweed [14 d]

EC50>1.0 mg/L

Eastern oyster [96 h]

EC50 41 mg/L slightly toxic

Saltwater mysid [96 h]

LC50 66 μg/L very highly toxic

Fate in :
Acetamiprid is reported to be an insect neurotoxicant but is 300 times less toxic to bees than other neo-nicotinoid insecticides such as imidacloprid and thiamethoxam. It is not bioaccumulative.
The Canadian PMRA recommends buffer zones to reduce the risks to marine or estuarine organisms and terrestrial plants. As acetamiprid is toxic to honeybees, it should not be applied when bees are present in the area being treated.
For drinking water, the estimated environmental concentrations in groundwater was 1.1 μg/L (using the model LEACHM).

Fate in soil:
Under aerobic conditions, acetamiprid is degraded within a few days in soil, mainly by microbial processes. Photolytic and hydrolytic degradation is minimal. Acetamiprid degrades rapidly in the environment to produce soil metabolites that are more persistent and possess low to moderate to high soil mobility. The metabolites have been shown to be toxicologically insignificant.
Laboratory biotransformation studies of acetamiprid were carried out using loam, sandy loam and clay loam soils from the UK, and loamy sand soil from Switzerland. Acetamiprid was found to have a half-life of 1-8 days at 20 with the formation of several major transformation products; and a half-life of approximately 7 days in a loam soil from the UK at 10℃,both under aerobic conditions. Although biotransformation studies were not carried out under anaerobic conditions it is expected that acetamiprid will be persistent, based on the anaerobic aquatic biotransformation study. In field studies in Canada, acetamiprid was non-persistent to slightly persistent in soil (DT50 5.2 - 17.8 days); therefore, no significant carryover of residues to the next field season is predicted. The major transformation products of acetamiprid showed a trend of declining concentrations in soil towards the end of the study. Leaching through the soil layers is unlikely due to the moderately rapid rate of degradation of the parent in soil. DT50 values of 2.8 - 14.1 days were obtained for acetamiprid in field studies in the US, and acetamiprid and its major transformation products were not detected below the 0-15 cm layer of soil.
Adsorption on soil:
Kd 0.34 - 4.1 ml/g, and Koc 157 - 298 ml/g (for two sandy loam soils, silt loam and clay)
From the Kocvalues, acetamiprid is moderately mobile in soil and has a moderate potential to partition into aquatic sediment.

Fate in aquatic systems:
Acetamiprid is very soluble in water which suggests high potential to leach in soil or to runoff in surface water. There is no potential for bioaccumulation. It is stable in water at pH 4, 5 and 7 at all temperatures and at pH 9 at 22, but is hydrolysed at pH 9 at 35 and 45 forming two major hydrolytic transformation products. Acetamiprid undergoes phototransformation at pH 7 with a half-life of 34 days.
Acetamiprid is slightly persistent (DT50 = 30 days at 25) in aerobic and persistent (DT50 = 365 days at 25) in anaerobic sediment-water systems.
Studies showed that acetamiprid poses a moderate risk to vegetative vigour but a low risk to seedling emergence by overspray on non-target vegetation. With regards to seedling emergence, onions were found to be the most sensitive monocotyledon and cucumber the most sensitive dicotyledon. Perennial ryegrass was found to be the most sensitive moncotyledon and lettuce the most sensitive dicotyledon in studies on the vegetative vigour.

Transport Information
Hazard Class:O (Obsolete as pesticide, not classified).

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