Cycloxaprid is a

neonicotinoid Neonicotinoids (sometimes shortened to neonics ) are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Royal Dutch Shell, Shell and Bayer in the 1980s. Neonicotinoids are among the widest-used insecti ...

insecticide 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, i ...

derived from the (nitromethylene)imidazole (NMI) analogue of

imidacloprid 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. ...

. First reported in 2008., it is a novel insecticide developed to control pests that have developed resistance to imidacloprid, particularly targeting lepidopteran pests and

whiteflies 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. Description and taxonomy The A ...

in rice cultivation. Currently, limited information is available regarding its environmental impact, ecotoxicology, or effects on human health.

Chemistry

Cycloxaprid is distinguished by its unique chemical structure, featuring a

nitro Nitro may refer to: Chemistry *Nitrogen, a chemical element and a gas except at very low temperatures, with which many compounds are formed: **Nitro compound, an organic compound containing one or more nitro functional groups, -NO2 **Nitro ligand ...

substituent in the ''cis''-configuration, unlike other commercialized neonicotinoids which have the nitro group in the ''trans''-configuration. It has demonstrated significant efficacy against insecticide-resistant pests, particularly showing 50-fold higher activity against imidacloprid-resistant

brown planthopper The brown planthopper (BPH), ''Nilaparvata lugens'' (Stål) (Hemiptera: Delphacidae) is a planthopper species that feeds on rice plants (''Oryza sativa'' L.). These insects are among the most important pests of rice, which is the major staple cro ...

compared to imidacloprid itself. This enhanced effectiveness against resistant pests makes it a promising alternative in pest management strategies, especially in contexts where repeated imidacloprid applications have led to resistance development.

Neonicotinoid Neonicotinoids (sometimes shortened to neonics ) are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Royal Dutch Shell, Shell and Bayer in the 1980s. Neonicotinoids are among the widest-used insecti ...

s represent the most commonly used class of insecticides globally, valued for their effectiveness against a wide spectrum of insect pests, particularly those in the orders

Coleoptera Beetles are insects that form the Taxonomic rank, order Coleoptera (), in the superorder Holometabola. Their front pair of wings are hardened into wing-cases, elytra, distinguishing them from most other insects. The Coleoptera, with about 40 ...

Diptera Flies are insects of the order Diptera, the name being derived from the Greek δι- ''di-'' "two", and πτερόν ''pteron'' "wing". Insects of this order use only a single pair of wings to fly, the hindwings having evolved into advance ...

, and

Lepidoptera Lepidoptera ( ) or lepidopterans is an order (biology), order of winged insects which includes butterflies and moths. About 180,000 species of the Lepidoptera have been described, representing 10% of the total described species of living organ ...

. Their applications span both agricultural crop protection and animal health, with common usage methods including plant, soil, and seed treatments. However, ecological concerns have emerged regarding their environmental impact. Studies have documented that

, a prominent neonicotinoid, can adversely affect various non-target organisms. These effects include impacts on

pollinator A pollinator is an animal that moves pollen from the male anther of a flower to the female carpel, stigma of a flower. This helps to bring about fertilization of the ovules in the flower by the male gametes from the pollen grains. Insects are ...

s and beneficial arthropods, manifesting in behavioral changes, population decline, reduced reproductive success, and increased mortality. Research has also revealed broader ecological consequences, including negative effects on aquatic

macroinvertebrate Invertebrates are animals that neither develop nor retain a vertebral column (commonly known as a ''spine'' or ''backbone''), which evolved from the notochord. It is a paraphyletic grouping including all animals excluding the chordate subphylum V ...

plankton Plankton are the diverse collection of organisms that drift in Hydrosphere, water (or atmosphere, air) but are unable to actively propel themselves against ocean current, currents (or wind). The individual organisms constituting plankton are ca ...

crayfish Crayfish are freshwater crustaceans belonging to the infraorder Astacidea, which also contains lobsters. Taxonomically, they are members of the superfamilies Astacoidea and Parastacoidea. They breathe through feather-like gills. Some spe ...

, and

mollusk Mollusca is a phylum of protostomic invertebrate animals, whose members are known as molluscs or mollusks (). Around 76,000 extant species of molluscs are recognized, making it the second-largest animal phylum after Arthropoda. The ...

s. Furthermore, studies have identified ecosystem-level impacts, such as disruption of

songbird A songbird is a bird belonging to the suborder Passeri of the perching birds (Passeriformes). Another name that is sometimes seen as the scientific or vernacular name is Oscines, from Latin ''oscen'', "songbird". The Passeriformes contains 5,00 ...

migration patterns and decreases in fishery productivity. These findings have motivated the development of alternative insecticides that maintain pest control efficacy while reducing environmental impact.

Mechanism of action

Cycloxaprid’s mode of action was initially believed to be analogous to that of imidacloprid, likely impacting

nicotinic acetylcholine receptor Nicotinic acetylcholine receptors, or nAChRs, are Receptor (biochemistry), receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the c ...

s However, the exact mode of action is not fully understood.

References

{{Reflist Insecticides Heterocyclic compounds with 3 rings Oxygen heterocycles Nitrogen heterocycles Chloropyridines Nitro compounds Disubstituted pyridines