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] 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. [3] [4]
Pymetrozine is a neuroactive insecticide that selectively affects chordotonal mechanoreceptors present in the legs of sap-feeding insects. [5] It targetes specific ion channels in the nervous system of insects, particularly the transient receptor potential vanilloid (TRPV) channels. [6] 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. [4] [7]
Pymetrozine can cause cancer according to The Environmental Protection Agency (EPA). [8] Pymetrozine is of low acute toxicity to humans, mammals, birds, aquatic organisms, and bees. [5] It is a respiratory tract irritant and ingestion may affect major organs at high doses. It may cause reproductive or developmental defects. [9]
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. [10] 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. [11] Exposure to 3-PCA has been reported to cause developmental toxicity in zebrafish. [12]
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). [13]
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.
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.
Cypermethrin (CP) is a synthetic pyrethroid used as an insecticide in large-scale commercial agricultural applications as well as in consumer products for domestic purposes. It behaves as a fast-acting neurotoxin in insects. It is easily degraded on soil and plants but can be effective for weeks when applied to indoor inert surfaces. It is a non-systemic and non-volatile insecticide that acts by contact and ingestion, used in agriculture and in pest control products. Exposure to sunlight, water and oxygen will accelerate its decomposition. Cypermethrin is highly toxic to fish, bees and aquatic insects, according to the National Pesticide Information Center (NPIC) in the USA. It is found in many household ant and cockroach killers, including Raid, Ortho, Combat, ant chalk, and some products of Baygon in Southeast Asia.
A mechanoreceptor, also called mechanoceptor, is a sensory receptor that responds to mechanical pressure or distortion. Mechanoreceptors are innervated by sensory neurons that convert mechanical pressure into electrical signals that, in animals, are sent to the central nervous system.
A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums. Pyrethroids are used as commercial and household insecticides.
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.
Fenitrothion is a phosphorothioate (organophosphate) insecticide that is inexpensive and widely used worldwide. Trade names include Sumithion, a 94.2% solution of fenitrothion.
Abamectin (also called avermectin B1) is a widely used insecticide and anthelmintic. Abamectin, is a member of the avermectin family and is a natural fermentation product of soil dwelling actinomycete Streptomyces avermitilis. Abamectin differs from ivermectin, the popular member of the avermectin family, by a double bond between carbons 22 and 25. Fermentation of Streptomyces avermitilis yields eight closely related avermectin homologs, with the B1a and B1b forms comprising the majority of the fermentation. The non-proprietary name, abamectin, refers to a mixture of B1a (~80%) and B1b (~20%). Out of all the avermectins, abamectin is the only one that is used both in agriculture and pharmaceuticals.
Demeton-S-methyl is an organic compound with the molecular formula C6H15O3PS2. It was used as an organothiophosphate acaricide and organothiophosphate insecticide. It is flammable. With prolonged storage, Demeton-S-methyl becomes more toxic due to formation of a sulfonium derivative which has greater affinity to the human form of the acetylcholinesterase enzyme, and this may present a hazard in agricultural use.
Sooty mold is a collective term for different Ascomycete fungi, which includes many genera, commonly Cladosporium and Alternaria. It grows on plants and their fruit, but also environmental objects, like fences, garden furniture, stones, and even cars. The mold benefits from either a sugary exudate produced by the plant or fruit, or honeydew-secreting insects or sap suckers the plant may be infested by.
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.
Thiamethoxam is the ISO common name for a mixture of cis-trans isomers used as a systemic insecticide of the neonicotinoid class. It has a broad spectrum of activity against many types of insects and can be used as a seed dressing.
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.
Novaluron, or (±)-1-[3-chloro-4-(1,1,2-trifluoro-2-trifluoro- methoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea, is a chemical with pesticide properties, belonging to the class of insecticides called insect growth regulators. It is a benzoylphenyl urea developed by Makhteshim-Agan Industries Ltd.. In the United States, the compound has been used on food crops, including apples, potatoes, brassicas, ornamentals, and cotton. Patents and registrations have been approved or are ongoing in several other countries throughout Europe, Asia, Africa, South America, and Australia. The US Environmental Protection Agency and the Canadian Pest Management Regulatory Agency consider novaluron to pose low risk to the environment and non-target organisms and value it as an important option for integrated pest management that should decrease reliance on organophosphorus, carbamate and pyrethroid insecticides.
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.
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, but the specific target site of the chemical is unknown. It is typically sold as wettable granules mixed with water before spraying.
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.
Diafenthioron is a pesticide, specifically an insecticide. It is a chemical compound which belongs to the thiourea group. Diafenthiuron is sold under the brand names Derby, Diron, Pegasus, Polar and Polo.