Fire ant

Mitex [2385-85-5] is l,2,3,4,5,5,6,7,8,9,10,10-dodecachloro-octahydro-l,3,4-metheno-2JT-cyclobuta-p,<7 -pentalene (37) (mp 485°C). The rat LD s are 306, 600 (oral) and >2000 (dermal) mg/kg. Mirex is extremely resistant to biodegradation and was once considered the perfect stomach poison iasecticide for use ia baits to control imported fire ants. However, even at doses of a few milligrams per 10 m it was found to bioaccumulate ia birds and fish and its registrations were canceled ia the United States ia 1976. 

Avermectins and Ivermectin. The avermectias are pentacycHc lactones isolated from fermentation products of Streptomjces avermitilis and ivermectin is a semisynthetic chemical, 22,23-dihydroavermectia (46). Ivermectin is effective in very low doses for the control of red spider mites on deciduous fmits, in baits for the control of imported fire ants, and as a parasiticide for Onchocerca volvulus in humans and for catde gmbs. These insecticides appear to function as agonists for the neuroinhibitory transmitter y-aminobutyric acid (GABA) (see Antiparasitic agents, avermectins). 

Outdoor Pests biting flies, fire ants, hornets, mosquitoes, ticks, wasps mice, moles snails, slugs mil dews, molds, mosses... 

Other ants, like the carpenter ant, are incapable of stinging, but that does not stop them from biting and then squirting formic acid into the wound. In this case, because the venom is not injected, a baking soda paste can quickly neutralize the venom and ease the pain. Fire ants, however, have toxic alkaloid venom. Regardless of whether the ant that bites or stings you has acidic or alkaline venom, however, one thing remains the same—it hurts ... 

The queen is usually reproductively dominant within the colony and uses chemical cues as both primer and releaser pheromones to suppress the production or fecundity of other sexuals, inhibit reproduction by worker castes, modulate reproductive behaviors (e.g., inhibit swarming and orient swarms), attract males, regulate worker tasks and worker ontogeny, and produce host repellents in slave-making species. Considering the importance of queen semiochemicals in social hymenoptera, few queen pheromones have been chemically identified. The queens of most social hymenopteran colonies are attractive to workers, allowing them to be properly tended as well as to facilitate the dissemination of other pheromone cues. However, the retinue pheromone has been chemically identified in very few species. In the 1980s, queen pheromone components were identified in the fire ant, Solenopsis invicta [91,92], and in the Pharaoh s ant, Monomoriumpharaonis [93]. 

Although many queen-produced pheromones are actively being studied in ants, particularly in the fire ant (Solenopsis invicta) [10,105-110], chemical identifications remain elusive. However, there have been a few recent advances in ants. The queen of the slave-making species Polyergus rufescens produces de-cyl butanoate 60 that repels host workers when upsurping a colony [111]. Males of Formica lugubris are attracted to alate queens by undecane 61, tridecane 62 and (4Z)-tridec-4-ene 63 [112]. 

Glancey BM (1986) The queen recognition pheromone of Solenopsis invicta. In Lofgren CS, Vander Meer RK (eds) Fire ants and leaf-cutting ants biology and management. Westview Press, Boulder, p 223... 

Williams, D.F. and C.S. Lofgren. 1983. Imported fire ant (Hymenoptera Formicidae) control evaluation of several chemicals for individual mound treatments. Jour. Econ. Entomol. 76 1201-1205. 

Phillips, S.A., Jr. D.M. Clabom, and O.F. Francke. 1984. Comparison of aerial application and single-mound drenches of fenvalerate against the red imported fire ant, Solenopsis invicta Buren, in Texas. Southwestern Entomol. 9 164-168. 

Widespread use of mirex may lead to altered population structure in terrestrial systems, with resurgence or escalation of nontarget pests due to selective mirex-induced mortality of predators (NAS 1978). For example, populations of immature horn flies and rove beetles, two species of arthropods normally preyed upon by fire ants, were higher in mirex-treated areas than in control areas (Howard and Oliver 1978). Conversely, other species, such as crickets, ground beetles, and various species of oil-loving ants, were directly affected and populations were still depressed or eliminated 14 months posttreatment (NAS 1978), whereas fire ants recovered to higher than pretreatment levels, as judged by mound numbers and mound size (Summerlin et al. 1977). 

Modified from Lowe, J.l. 1982. Mirex, fire ants, and estuaries. Pages 63-70 in Proceedings of the Workshop on Agrichemicals and Estuarine Productivity. Duke Univ. Mar. Lab., Beaufort, NC. Sept. 18-19, 1980. U.S. Dep. Comm. NOAA/OMPA. 

Modified from Wheeler, W.B., D.P. Jouvenay, D.P. Wojcik, W.A. Banks, C.H. Van Middelem, C.S. Lofgren, S. Nesbitt, L. Williams, and R. Brown. 1977. Mirex residues in nontarget organisms after application of 10-5 bait for fire ant control, Northeast Florida—1972-74. Pestic. Monitor. Jour. 11 146-156. 

Mirex (dodecachlorooctahydro-l,3,4-metheno-2H-cyclobuta [tv/] pentalene) has been used extensively in pesticidal formulations to control the red imported fire ant (Solenopsis invicta), and as a flame retardant in electronic components, plastics, and fabrics. One environmental consequence of mirex was the severe damage recorded to fish and wildlife in nine southeastern states and the Great Lakes, especially Lake Ontario. In 1978, the U.S. Environmental Protection Agency banned all further use of mirex, partly because of the hazards it imposed on nontarget biota. These included ... 

Howard, F.W. and A.D. Oliver. 1978. Arthropod populations in permanent pastures treated and untreated with mirex for red imported fire ant control. Environ. Entomol. 7 901-903. 

Sodium molybdate and other molybdenum compounds in toxic baits have potential for termite control (Brill et al. 1987). Baits containing 1000 mg Mo/kg were fatal to 99% of the termite Reticu-litermes flavipes in 48 days. After 8 to 10 days, termites became steel-gray in color, but appeared otherwise normal. Mortality began only after day 16. Termites did not avoid the poisoned bait, even at concentrations of 5000 mg Mo/kg. Yoshimura et al. (1987) reported similar results with another species of termite sodium molybdate killed 100% of the workers in a colony of Copotermes formo-sanus within 24 h after eating filter paper treated with a 5% solution. Some other species of insects — including fire ants (Solenopsis sp.) and various species of beetles and cockroaches — were not affected when exposed to baits containing 5000 mg Mo/kg for 48 days (Brill et al. 1987). 

Besides piperidine alkaloids, a total of 19 pyrrolidines have been found in the secretions of thief ants and fire ants of the genera Solenopsis and Monomorium. Among these, compounds 80-84 are simple pyrrolidines with two saturated linear all-carbon side chains only in Solenopsis latinode is there a secondary amine (82) and its methylated analog (85). One or two terminal unsaturations are present in compounds 86-91, which all possess a (hex-l-en)-6-yl chain and a 5-, 7-, or 9-carbon saturated chain. Compounds 93, 94, 96, 97, and 98 are the A-l-pyrrolines corresponding to pyrrolidines 80, 82, 90 (93 and 96 corresponding to 80, 94 to 82, and 97 and 98 to 90). 

Mirex and chlordecone are no longer made or used in the United States. Mirex and chlordecone were most commonly used in the 1960s and 1970s. Mirex was used as a pesticide to control fire ants mostly in the southeastern part of the United States. It was also used extensively as a flame retardant additive under the trade name Dechlorane in plastics, rubber, paint, paper, and electrical goods from 1959 to 1972 because it does burn easily. Chlordecone was used to control insects that attacked bananas, citrus trees with no fruits, tobacco, and ornamental shrubs. It was also used in household products such as ant and roach traps. Chlordecone is also known by its trade name Kepone . All registered products containing mirex and chlordecone were canceled in the United States between 1977 and 1978. 

Mirex has been found in human adipose tissue (Burse et al. 1989 Kutz et al. 1974). Although the route of exposure was not specified, exposure was probably via the inhalation, oral, and dermal routes. Levels of 0.16-5.94 ppm and 0.3-1.13 ppm in males and females, respectively, were found in tissue samples taken either from postmortem examinations or during surgery (Kutz et al. 1974). The adipose tissue samples came from individuals who lived in areas in which mirex was used extensively in a program to control fire ants. Adipose tissue levels of mirex ranging from 0.03 to 3.72 ppm have been found in residents living near a dump site in Tennessee (Burse et al. 1989). 

Epidemiological and Human Dosimetry Studies. No epidemiological studies are available for mirex exposure. Individuals living in areas that have been treated for fire ants or near hazardous waste sites containing mirex or chlordecone are the most likely exposed subpopulation because of the relatively long half-lives of these substances-estimated half-life of 10 years-(Carlson et al. 1976 ... 

As a result of human health concerns, production of mirex ceased in 1976, at which time industrial releases of this chemical to surface waters were also curtailed. However, releases from waste disposal sites continue to add mirex to the environment. Virtually all industrial releases of mirex were to surface waters, principally Lake Ontario via contamination of the Niagara and Oswego Rivers. About 75% of the mirex produced was used as a fire retardant additive, while 25% was used as a pesticide. As a pesticide, mirex was widely dispersed throughout the southern United States where it was used in the fire ant eradication program for over 10 years. 

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