Starlicide

Starlicide
IUPAC name 3-Chloro-4-methylaniline
Other names 3-Chloro-4-methylbenzenamine; 2-Chloro-4-aminotoluene; 3-Chloro-p-toluidine; Gull toxicant; DRC-1339; CPTH
Identifiers
CAS number	33240-95-8
PubChem	7255
ChemSpider	6985
Jmol-3D images	Image 1
SMILES Clc1cc(N)ccc1C
InChI InChI=InChI=1S/C7H8ClN/c1-5-2-3-6(9)4-7(5)8/h2-4H,9H2,1H3
Properties[1]
Molecular formula	C7H8ClN
Molar mass	141.6 g mol−1
Appearance	Yellow to brown liquid
Density	1.167 g/cm3
Melting point	24 °C, 297 K, 75 °F
Boiling point	237-238 °C
Solubility in water	Soluble in hot water
Hazards
Flash point	100 °C
LD50	1500 mg/kg (oral, rat)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Starlicide or gull toxicant is a chemical avicide that is highly toxic to European starlings and gulls, but less toxic to other birds or to mammals such as humans and pets.

Synonyms

The name Starlicide originated as a registered trademark of the animal feed manufacturer Ralston-Purina in St. Louis, Missouri.^[2] Starlicide is a small molecule in which a central benzene ring is modified by amine, chloro and methyl substituents in a specific pattern. Because special names exist for benzene rings modified with one or two of these functional groups, several synonymous chemical names may be encountered: 3-chloro-4-methylaniline or 3-chloro-4-methylbenzenamine, 2-chloro-4-aminotoluene, or 3-chloro-p-toluidine.^[3] Numbered groups (2-chloro, 4-amino) also may be named out of order; the numbers of such groups equal the number of carbon atoms in the benzene ring separating them from the group implied in the special name.

Preparations of this chemical may be named as a hydrochloride (e.g. "3-chloro-p-toluidine hydrochloride", CPTH), indicating that hydrochloric acid has been used to neutralize the molecule to a salt in which the amine group is protonated and a chloride counterion is present; otherwise the free base is indicated. The chemical salt is also known as DRC-1339.

Use

In 1966 it was reported that Starlicide is lethal to starlings with an acute oral LD₅₀ of 3.8 milligrams per kilogram body weight, but less toxic to most other birds. Grain-eating game birds [such as bobwhite quail,^[4] pheasants (Phasianus colchicus) and rooks (Corvus frugilegus)^[5]] were acknowledged to be more vulnerable. Hawks and mammals were resistant to the poison. Starlings were killed in a slow, "nonviolent" death by uremic poisoning and congestion of major organs.^[6] The effect was described as "a grayish white, frost-like material of uric acid overlaying the serosal surfaces of the various organs, accompanied by sterile inflammation and necrosis in the affected and adjacent tissues" akin to avian visceral gout.^[5] The site of action is believed to be in the kidney^[7]

Uses for CPTH include killing blackbirds on sprouting rice^[8] and on corn and soybean fields.^[9] For these and other uses the poison is often given with brown rice. Research continues to improve the effectiveness of delivery on brown rice by causing the poison to be retained on the bait longer and resist degradation by sunlight.^[10][11] The effect of the poison is believed to be cumulative: for example, the LC₅₀ for starlings was 4.7 ppm over 30 days, but only 1.0 ppm when fed for 90 days.^[4]

In 2009, a culling with DRC-1339 received national attention after USDA employees dispensed the poison in Griggstown, New Jersey to kill an estimated 5,000 starlings that plagued feed lots and dairies on local farms. When "it began raining birds" community members became alarmed, unsure whether a toxin or disease was at work. Two property owners in the area reported collecting over 150 birds each from their land.^[12][13]

In January 2011, there was another incident in Yankton, South Dakota, causing public alarm. The USDA had poisoned the birds in Nebraska to protect farmers feeds.

See also

• Diclofenac

References

1. ^ 3-Chloro-4-methylaniline, chemicalland21.com
2. ^ Knittle, C.E.; Guarino, J.L.; Nelson, P.C.; Dehaven, R.W.; Twedt, D.J.: Baiting Blackbird and Starling Congregating Areas in Kentucky and Tennessee, Proc. of the 9th Vertebrate Pest Conference (1980), Lincoln, NE; p. 31, footnote [1]
3. ^ "starlicide - Compound Summary (CID: 7255)". NCBI. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7255&loc=ec_rcs. 
4. ^ ^{a b} Schafer Jr, EW; Bruton, RB; Cunningham, DJ; Lockyer, NF (1977). "The chronic toxicity of 3-chloro-4-methyl benzamine HCl to birds". Archives of environmental contamination and toxicology 6 (2–3): 241–8. doi:10.1007/BF02097765. PMID 901004. 
5. ^ ^{a b} Nikodémusz, E; Imre, R (1982). "Pathological features of 3-chloro-4-methyl benzamine HCl toxicity in rooks (Corvus frugilegus L.) and pheasants (Phasianus colchicus L.)". Gegenbaurs morphologisches Jahrbuch 128 (5): 753–61. PMID 7152225. 
6. ^ Thomas J. Decino, Donald J. Cunningham and Edward W. Schafer (April 1966). "Toxicity of DRC-1339 to starlings". Journal of Wildlife Management 30 (2): 249–253. doi:10.2307/3797809. JSTOR 3797809. 
7. ^ Goldade, DA; Tessari, JD; Johnston, JJ (2004). "Absorption, distribution, and excretion of 14C-3-chloro-4-methylaniline hydrochloride in two species of birds following a single oral dose". Journal of agricultural and food chemistry 52 (26): 8074–80. doi:10.1021/jf0493977. PMID 15612798. 
8. ^ Johnston, JJ; Holmes, MJ; Hart, A; Kohler, DJ; Stahl, RS (2005). "Probabilistic model for estimating field mortality of target and non-target bird populations when simultaneously exposed to avicide bait". Pest management science 61 (7): 649–59. doi:10.1002/ps.1040. PMID 15747324. 
9. ^ Linz, GM; Knutsen, GA; Homan, HJ; Bleier, WJ (2004). "Attractiveness of brown rice baits to non-target birds in harvested corn and soybean fields". Pest management science 60 (11): 1143–8. doi:10.1002/ps.913. PMID 15532691. 
10. ^ Hurley, JC; Volz, SA; Johnston, JJ (1999). "Stabilization of the avicide 3-chloro-p-toluidine as the beta-cyclodextrin adduct". Journal of agricultural and food chemistry 47 (7): 2904–7. doi:10.1021/jf981127z. PMID 10552584. 
11. ^ Stahl, RS; Furcolow, C; Hurley, JC; Johnston, JJ (2005). "Characterizing 3-chloro-p-toluidine hydrochloride on rough-hulled rice and ethyl-cellulose-coated rice baits using high-performance liquid chromatography". Journal of chromatographic science 43 (7): 367–71. PMID 16176650. 
12. ^ Victor Epstein (2009-01-27). "Bird culling fallout alarms New Jersey community". http://www.msnbc.msn.com/id/28870575/. 
13. ^ "Dead birds horrify and anger Franklin residents". 2009-01-26. http://www.app.com/article/20090126/NEWS/90126028.