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]
Companion planting in gardening and agriculture is the planting of different crops in proximity for any of a number of different reasons, including weed suppression, pest control, pollination, providing habitat for beneficial insects, maximizing use of space, and to otherwise increase crop productivity. Companion planting is a form of polyculture.
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.
The avermectins are a group of 16-membered macrocyclic lactone derivatives with potent anthelmintic and insecticidal properties. These naturally occurring compounds are generated as fermentation products by Streptomyces avermitilis, a soil actinomycete. Eight different avermectins were isolated in four pairs of homologue compounds, with a major (a-component) and minor (b-component) component usually in ratios of 80:20 to 90:10. Avermectin B1, a mixture of B1a and B1b, is the drug and pesticide abamectin. Other anthelmintics derived from the avermectins include ivermectin, selamectin, doramectin, eprinomectin.
Fenoxycarb is an insect growth regulator. It has a low toxicity for bees, birds, and humans, but is toxic to fish. The oral LD50 for rats is greater than 16,800 milligrams per kilogram (0.269 oz/lb).
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.
Metaflumizone is a semicarbazone broad-spectrum insecticide developed by Nihon Nohyaku with activity on Lepidoptera, Coleoptera, and certain Hemiptera. It is also used for the veterinary treatment of fleas and ticks, marketed under the brand name ProMeris. A discontinued variant of ProMeris, called ProMeris Duo or Promeris for Dogs, was indicated for canine use and was a formulated blend of metaflumizone and amitraz. The metaflumizone-only formulation is waterproof and typically remain effective for 30–45 days in a cutaneous application at the base of the neck.
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.
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.
Cyantraniliprole is an insecticide of the diamide class. It shows strong activity and lepidoptera (caterpillars), and since it shows systemic activity it is also active against sucking pests such as aphids and whitefly.
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.
Tebufenpyrad is an insecticide and acaricide widely used in greenhouses. It is a white solid chemical with a slight aromatic smell. It is soluble in water and also in organic solvents.
Spirotetramat is a keto-enol insecticide developed by Bayer CropScience under the brand names Movento and Ultor.
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.
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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