Names | |
---|---|
IUPAC name 6-methyl-4-[(E)-pyridin-3-ylmethylideneamino]-2,5-dihydro-1,2,4-triazin-3-one | |
Other names Pymetrozin, Fulfill, Plenum, Endeavor | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.121.006 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
Properties | |
C10H11N5O | |
Molar mass | 217.23 g/mol |
Density | 1.36 g/cm3 |
Melting point | 217 °C |
2.25g/l 20 °C(Ethanol); 290mg/l, 25 °C (Water); <0.001g/l, 20 °C (Hexane) | |
Hazards | |
GHS labelling: [1] | |
Warning | |
H332, H351, H361fd, H410, H412 | |
P201, P273, P280, P301, P308+P313 | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 5820 mg/kg, Oral (Rat); >2000 mg/kg, percutaneous (Rat); >2000 mg/kg, oral (Bobwhite quail) |
LC50 (median concentration) | >100 mg/l, (96 hr) (Rainbow trout); >5200 ppm, (8 day) (Bobwhite quail) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Pymetrozine is an insecticide in the pyridine-azomethine chemical class, primarily utilized for controlling homopteran pests, such as aphids and whiteflies, in agricultural settings. [2] [3] Its mode of action selectively targets the feeding behavior of sap-feeding insects, causing them to cease feeding soon after ingestion. This unique mechanism limits its impact on non-target organisms, including beneficial insects. Pymetrozine has been extensively used on rice, potatoes, a wide variety of vegetable brassica crops and various other crops as an alternative to organophosphorus pesticides. [4] [5]
Pymetrozine is a neuroactive insecticide that selectively affects chordotonal mechanoreceptors present in the legs of sap-feeding insects. [6] It targetes specific ion channels in the nervous system of insects, particularly the transient receptor potential vanilloid (TRPV) channels. [7] [3] It is in IRAC group 9B. [8] These channels, which consist of two key protein subunits, play a crucial role in sensory signal transduction. When pymetrozine binds to these channels, it alters their activity, leading to increased sensitivity and disruption of normal neuronal signaling. This mechanism results in impaired movement and behavior in target insects. Pymetrozine acts both on the plant's surface and internally, moving through vascular channels in multiple directions. It penetrates leaf tissues and remains effective when applied to either foliage or soil. Its internal movement within the plant does not interfere with growth processes, even after leaf-based applications. [5] [9]
Pymetrozine can cause cancer according to The Environmental Protection Agency (EPA). [10] Pymetrozine is of low acute toxicity to humans, mammals, birds, aquatic organisms, and bees. [6] It is a respiratory tract irritant and ingestion may affect major organs at high doses. It may cause reproductive or developmental defects. [11]
Pymetrozine has low off-target effects.
The half-life of pymetrozine in water, soil, and rice plants is 2.81, 6.95, and 3.70 days respectively. [12] 3-pyridinecarboxaldehyde (3-PCA) and 4-amino-6-methyl-2 H-1,2,4-triazine-3-one are the primary degradation products of pymetrozine on photodegradation. [13] Exposure to 3-PCA has been reported to cause developmental toxicity in zebrafish. [14]
The annual usage of pymetrozine was at least 4.45 × 103 t in China according to its consumption (150 g/ha) and area of rice field (2.97 × 107 ha). [15]
Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, industrial buildings, for vector control, and control of insect parasites of animals and humans.
Pesticide resistance describes the decreased susceptibility of a pest population to a pesticide that was previously effective at controlling the pest. Pest species evolve pesticide resistance via natural selection: the most resistant specimens survive and pass on their acquired heritable changes traits to their offspring. If a pest has resistance then that will reduce the pesticide's efficacy – efficacy and resistance are inversely related.
Whiteflies are Hemipterans that typically feed on the undersides of plant leaves. They comprise the family Aleyrodidae, the only family in the superfamily Aleyrodoidea. More than 1550 species have been described.
Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action. Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.
Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class.
Methoprene is a juvenile hormone (JH) analog which acts as a growth regulator when used as an insecticide. It is an amber-colored liquid with a faint fruity odor.
Cyhalothrin is an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids, such as cyhalothrin, are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.
Indoxacarb is an oxadiazine pesticide developed by DuPont that acts against lepidopteran larvae. It is marketed under the names Indoxacarb Technical Insecticide, Steward Insecticide and Avaunt Insecticide. It is also used as the active ingredient in the Syngenta line of commercial pesticides: Advion and Arilon.
An insect growth regulator (IGR) is a chemical insecticide that kills insects indirectly by disrupting their life cycles. The term was initially proposed to describe the effects of juvenile hormone analogs. Although the term "insect growth disruptor" more accurately describes the actions of IGRs, it did not become widely used. IGRs encompass chemical classes with three modes of action : juvenile hormone analogs, chitin synthesis inhibitors, and ecdysone receptor agonists.
Tefluthrin is the ISO common name for an organic compound that is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as tefluthrin are often preferred as active ingredients in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. It is effective against soil pests because it can move as a vapour without irreversibly binding to soil particles: in this respect it differs from most other pyrethroids.
TRPN is a member of the transient receptor potential channel family of ion channels, which is a diverse group of proteins thought to be involved in mechanoreception. The TRPN gene was given the name no mechanoreceptor potential C (nompC) when it was first discovered in fruit flies, hence the N in TRPN. Since its discovery in fruit flies, TRPN homologs have been discovered and characterized in worms, frogs, and zebrafish.
Diamide insecticides are a class of insecticides, active mainly against lepidoptera (caterpillars), which act on the insect ryanodine receptor. They are diamides of either phthalic acid or anthranilic acid, with various appropriate further substitutions.
Sulfoxaflor, also marketed as Isoclast, is a systemic insecticide that acts as an insect neurotoxin. A pyridine and a trifluoromethyl compound, it is a member of a class of chemicals called sulfoximines, which act on the central nervous system of insects.
Rhopalosiphum rufiabdominale, the rice root aphid or red rice root aphid, is a sap-sucking insect pest with a wide host range and a global distribution. As a member of the superfamily Aphidoidea, it is one of 16 species of the genus Rhopalosiphum. Adults and nymphs are soft-bodied and usually dark green with brown, red, or yellow tones. Like all aphids, reproduction is sexual and asexual, depending on the environmental conditions and host plant. Rice root aphids cause injury to external plant parts, namely the roots or stem, by feeding on plant sap and vector several important plant viruses. The hosts of this pest extend across multiple plant families with most belonging to Rosaceae, Poaceae, and Solanaceae. R. rufiabdominale is universally associated with Prunus species but also infests various field crops, greenhouse vegetables, cannabis, and other ornamental plants. While this aphid originates from east Asia, it spans nearly every continent. Dispersal is particularly widespread across the United States, India, and Australia, with crop damage documented in multiple instances, although economic losses are primarily associated with Japanese rice crops. Nonetheless, it remains a pest of serious concern due to its high mobility, discrete habitat, and adaptive plasticity, giving it the rightful reputation as a successful invader.
The Insecticide Resistance Action Committee (IRAC) was formed in 1984 and works as a specialist technical group of the industry association CropLife to be able to provide a coordinated industry response to prevent or delay the development of insecticide resistance in insect and mite pests. IRAC strives to facilitate communication and education on insecticide and traits resistance as well as to promote the development and facilitate the implementation of insecticide resistance management strategies.
Flonicamid is a pyridine organic compound used as an insecticide on aphids, whiteflies, and thrips. It disrupts insect chordotonal organs that can affect hearing, balance, movement to cause cessation of feeding, by inhibiting nicotinamidase. It is in IRAC group 29. It is typically sold as wettable granules mixed with water before spraying.
Chlorantraniliprole is an insecticide of the diamide class used for insects found on fruit and vegetable crops as well as ornamental plants.
Nereistoxin is a natural product identified in 1962 as the toxic organic compound N,N-dimethyl-1,2-dithiolan-4-amine. It had first been isolated in 1934 from the marine annelid Lumbriconereis heteropoda and acts by blocking the nicotinic acetylcholine receptor. Researchers at Takeda in Japan investigated it as a possible insecticide. They subsequently developed a number of derivatives that were commercialised, including those with the ISO common names bensultap, cartap, thiocyclam and thiosultap.
Broflanilide is a complex, polycyclic, organohalogen insecticide which provides a novel mode of action (MoA).
Flupyradifurone is a systemic butenolide insecticide developed by Bayer CropScience under the name Sivanto. Flupyradifurone protects crops from sap-feeding pests such as aphids and is safer for non-target organisms compared to other insecticides. Sivanto was launched in 2014 since it obtained its first commercial registration in central America. Insecticide Resistance Action Committee (IRAC) classified Flupyradifurone as 4D subset (butenolide) and it is the first pesticide in the butenolide category. It was approved by European Union in 2015.
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