331:
256:
696:. AChE is an enzyme that hydrolyzes acetylcholine, an excitatory neurotransmitter. When acetylcholine is released into the synaptic cleft, the postsynaptic action is not terminated by reuptake. Rather, the acetylcholine is broken down by AChE into acetate and choline which is then taken up by the presynaptic terminal where the choline together with acetyl CoA is resynthesized into acetylcholine. AChE is therefore present in high concentrations in the synaptic cleft.
935:
the rats showed excitement additional to the aforementioned effects. When EPN was administered to cats via the skin, similar behavior was observed, although the animals showed signs of paralysis without anesthesia instead of fasciculations. Overall, it can be stated that an overdose of EPN results in convulsions and tremor and eventually causes death. The period till death after administration of a lethal dose of EPN is, however, not listed.
758:
including different types of rodents, different types of birds and even cats and dogs. EPN has been administered to the animal test subjects via different ways of exposure including oral-, skin-, eye-, intraperitoneal- and subcutaneous administration>. Exposure to humans can happen through inhalation of the aerosol, ingestion and absorption through skin. There is no reliable information available on
126:
22:
934:
When rats inhaled a lethal dose of EPN, they showed muscle twitches (fasciculations) originating from the peripheral nervous system. Furthermore, convulsions of the lungs and thorax were observed along with shortness of breath. However, when a lethal dose of EPN was administered via the skin to rats,
765:
values in humans. However, the recommended limits of skin exposure to EPN, stated by the
American Conference of Governmental Industrial Hygienists (ACGIH) in 2008, were a time weighted average of 0.5 mg/m and a short term exposure level of 2 mg/m. Additionally when human volunteers were fed
748:
effective against orchard pests, including apple flea weevil, plum curculio, and codling moth and for some soil insects. It is also good to use against the following pests: rice stem borer, boll weevils, oriental fruit moth, fruit moths, codling moths, cotton bollworms, peachtree borers, pear psylla,
699:
EPN can enter the nervous system readily due to it being lipophilic in nature. Here it inhibits AChE by binding to a serine residue located at the active site of AChE. The subsequent lack of acetylcholine hydrolysis causes accumulation of acetylcholine at cholinergic synapses. This in turn causes
952:
There is no specific antidote listed for EPN. Symptoms of acute poisoning by EPN develop during exposure or in the following twelve hours. These symptoms range from dizziness and headaches, to tremor, muscle twitching and if exposed to a high dose even to respiratory deficiency. Since EPN is an
757:
In humans, EPN causes various symptoms including sweating, tearing, weakness, headache, dizziness, nausea, vomiting, tightness in chest, seizures, loss of consciousness, diarrhea, and abdominal cramps. The toxicity of EPN has been determined by performing animal experiments on various species,
943:
Different countries have set different limits of acceptable occupational toxicity of EPN. These values range from 0.1 to 0.5 mg/m via skin exposure. Chronic effects were not observed when hens were fed 18 ppm EPN for 21 months. When fed 54 ppm for 21 months, signs of delayed
953:
organophosphorus compound that inhibits acetylcholinesterase (AChE), it is advised to administer atropine sulfite intravenously or intramuscularly until atropinization is achieved. This atropinization can take up to 12 hours and must be repeated in order to have the desired effect.
708:
EPN itself is not directly toxic; the phosphorus-sulfur group is biotransformed into a phosphorus-oxygen group. The newly obtained oxygen analog is the compound that inhibits. Furthermore, EPN has been observed to yield different metabolic products in animals, including as
679:
Both these compounds have a (+)- and a (−)-isomer. There is no apparent differences in the rate of hydrolysis of these isomers, but the (+)-isomer of both EPN and EPNO is more toxic to house flies. While the (+)- and (−)-isomers, and the
1018:
981:
766:
6 mg of EPN per day for 47 days, no effect was found. When the daily dose was raised to 9 mg for 57 days, a reversible inhibition of blood cholinesterase was found. In
552:
380:
213:
1109:
749:
aphids, scale, budmoths, leafrollers, mites, European cornborers, aphids, thrips, armyworms, leaf miners, mexican beetles and many others.
39:
345:
105:
1455:
977:
86:
1450:
693:
43:
58:
684:
of both isomers of EPN, are equally toxic to mice. The (+)-isomer of EPNO is more toxic to mice than the (−)-EPNO isomer.
609:
1075:
1058:
288:
65:
1603:
309:
2309:
2097:
1410:
1102:
576:
563:
32:
2282:
1530:
1425:
1241:
1173:
72:
2319:
676:-nitrophenyl phenylphosphonate). EPNO differs from EPN by having an oxygen atom in place of the sulfur atom.
2275:
2233:
1286:
54:
251:
2254:
2214:
1266:
2324:
2314:
2268:
1095:
1415:
736:-nitrophenol can be further metabolized in the liver. The remaining amine is still a weak inhibitor.
637:
138:
2247:
1977:
1573:
1435:
1430:
1246:
1231:
633:
326:
179:
2240:
2226:
2122:
1923:
1653:
1445:
1440:
1261:
1223:
759:
2058:
1276:
1188:
692:
EPN, via its oxygen analog EPNO generated by metabolism, causes delayed neurotoxicity. It is an
354:
InChI=1S/C14H14NO4PS/c1-2-18-20(21,14-6-4-3-5-7-14)19-13-10-8-12(9-11-13)15(16)17/h3-11H,2H2,1H3
2103:
364:
InChI=1/C14H14NO4PS/c1-2-18-20(21,14-6-4-3-5-7-14)19-13-10-8-12(9-11-13)15(16)17/h3-11H,2H2,1H3
1997:
1783:
1778:
1743:
1703:
1251:
79:
1982:
1713:
1583:
629:
492:
403:
297:
233:
2261:
2180:
1563:
1548:
681:
645:
189:
330:
255:
2078:
1558:
1397:
603:
2303:
2162:
2043:
1987:
1959:
1866:
1856:
1688:
1668:
1334:
1299:
722:
481:
471:
244:
2205:
2147:
2142:
2048:
2023:
1954:
1949:
1919:
1891:
1846:
1841:
1836:
1821:
1768:
1673:
1643:
1568:
1543:
1505:
1387:
1377:
1362:
1357:
1347:
1324:
1304:
1153:
1118:
985:
277:
2220:
2137:
2038:
2028:
1939:
1915:
1906:
1886:
1881:
1871:
1831:
1806:
1788:
1598:
1382:
1352:
1342:
1294:
1271:
1178:
1168:
1122:
1039:. National Institute for Occupational Safety and Health (NIOSH). 4 December 2014
782:
values of EPN for different routes of exposure administered to various organisms
649:
625:
532:
508:
21:
2172:
2152:
2083:
2073:
2063:
2053:
2033:
2013:
1944:
1934:
1901:
1896:
1876:
1861:
1851:
1826:
1816:
1811:
1798:
1748:
1718:
1658:
1638:
1623:
1618:
1613:
1593:
1515:
1490:
1480:
1372:
1367:
1319:
1309:
1236:
1183:
1163:
1148:
1081:
1032:
1014:
440:
224:
125:
1087:
2118:
2113:
2108:
2093:
1992:
1929:
1911:
1728:
1708:
1698:
1678:
1663:
1578:
1553:
1520:
1420:
1314:
1208:
1198:
1143:
1130:
745:
2288:
2190:
2185:
2157:
2132:
2088:
2068:
1773:
1758:
1648:
1633:
1588:
1538:
1475:
1256:
1213:
1193:
1158:
1138:
641:
2126:
2018:
1969:
1763:
1753:
1733:
1723:
1683:
1608:
1500:
1470:
461:
264:
1738:
1628:
1495:
1485:
1405:
1203:
729:
602:
Except where otherwise noted, data are given for materials in their
1693:
1510:
212:
202:
2195:
1465:
589:
1091:
1460:
15:
1061:. Pesticide Management Education Program, Cornell University.
1037:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
314:
1019:
National
Institute for Occupational Safety and Health
982:
National
Institute for Occupational Safety and Health
717:-ethyl phenylphosphonic acid, phenylphosphonic acid,
2204:
2171:
2006:
1968:
1797:
1529:
1396:
1333:
1285:
1222:
1129:
46:. Unsourced material may be challenged and removed.
774:values for various non-human species are listed.
700:cholinergic receptors to become overstimulated.
668:-nitrophenyl phenylphosphonothionate) and EPNO (
276:
188:
1103:
163:-nitrophenyl thionobenzenephosphonate, Ethyl
8:
713:-aminophenyl ethyl benzenethiophosphonate,
1110:
1096:
1088:
329:
254:
232:
117:
296:
106:Learn how and when to remove this message
1013:NIOSH Pocket Guide to Chemical Hazards.
978:"EPN International Chemical Safety Card"
788:
632:class. It is used against pests such as
972:
970:
968:
966:
962:
385:
350:
325:
150:-(4-nitrophenyl) phenylphosphonothioate
1082:NIOSH Pocket Guide to Chemical Hazards
1008:
1006:
1004:
1002:
245:
694:acetylcholinesterase (AChE) inhibitor
357:Key: AIGRXSNSLVJMEA-UHFFFAOYSA-N
167:-nitrophenyl benzenethionophosphonate
7:
660:EPN is available in two forms, EPN(
476:36 °C (97 °F; 309 K)
44:adding citations to reliable sources
721:-ethyl phenylphosphonothioic acid,
367:Key: AIGRXSNSLVJMEA-UHFFFAOYAT
267:
430:
14:
388:CCOP(=S)(c1ccccc1)Oc2ccc(cc2)()=O
456:Light yellow crystalline powder
421:
415:
124:
20:
606:(at 25 °C , 100 kPa).
31:needs additional citations for
433:
424:
409:
1:
944:neurotoxicity were observed.
557:(US health exposure limits):
1604:Diisopropyl fluorophosphate
869:2.37 mg/kg bodyweight
845:4.21 mg/kg bodyweight
837:12.2 mg/kg bodyweight
744:EPN is an insectide and an
521:or concentration (LD, LC):
2341:
786:All data was derived from
2283:Purpureocillium lilacinum
1242:Chromated copper arsenate
1174:m-Cumenyl methylcarbamate
884:
821:20 mg/kg bodyweight
806:
600:
551:
547:12.2 mg/kg (oral, mouse)
517:
502:
396:
376:
341:
172:
156:
137:
132:
123:
1287:Insect growth regulators
861:7 mg/kg bodyweight
853:5 mg/kg bodyweight
829:3 mg/kg bodyweight
813:5 mg/kg bodyweight
2276:Paenibacillus popilliae
2255:Metarhizium anisopliae
2234:Beauveria brongniartii
2215:Bacillus thuringiensis
1267:Lead hydrogen arsenate
1059:"EPN Chemical Profile"
55:"EPN" insecticide
2269:Lecanicillium lecanii
939:Occupational toxicity
1416:Carbon tetrachloride
543:36 mg/kg (oral, rat)
539:20 mg/kg (oral, dog)
139:Preferred IUPAC name
40:improve this article
2248:Metarhizium acridum
1978:Chlorantraniliprole
1574:Chlorpyrifos-methyl
1247:Copper(II) arsenate
1232:Aluminium phosphide
1224:Inorganic compounds
688:Mechanism of action
634:European corn borer
545:7 mg/kg (oral, rat)
541:8 mg/kg (oral, rat)
493:Solubility in water
448: g·mol
120:
2241:Isaria fumosorosea
2227:Beauveria bassiana
2123:Piperonyl butoxide
1924:chrysanthemic acid
1262:Diatomaceous earth
792:Route of exposure
610:Infobox references
592:(Immediate danger)
486:215°C at 0.667kPa
118:
2310:Phosphonothioates
2297:
2296:
2098:+milbemycin oxime
1779:Tetrachlorvinphos
1744:Pirimiphos-methyl
1704:Oxydemeton-methyl
1252:Copper(I) cyanide
927:
926:
880:106 mg/m/1H
618:Chemical compound
616:
615:
310:CompTox Dashboard
214:Interactive image
116:
115:
108:
90:
2332:
1983:Cyantraniliprole
1714:Parathion-methyl
1584:Demeton-S-methyl
1531:Organophosphorus
1112:
1105:
1098:
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1062:
1055:
1049:
1048:
1046:
1044:
1029:
1023:
1022:
1010:
997:
996:
994:
993:
984:. Archived from
974:
789:
630:phosphonothioate
447:
435:
432:
426:
423:
417:
411:
404:Chemical formula
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333:
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269:
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216:
192:
128:
121:
111:
104:
100:
97:
91:
89:
48:
24:
16:
2340:
2339:
2335:
2334:
2333:
2331:
2330:
2329:
2320:Nitro compounds
2300:
2299:
2298:
2293:
2262:Nomuraea rileyi
2200:
2167:
2007:Other chemicals
2002:
1964:
1793:
1564:Chlorfenvinphos
1549:Azinphos-methyl
1525:
1398:Organochlorides
1392:
1329:
1281:
1277:Scheele's Green
1218:
1125:
1116:
1078:, toxipedia.org
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1052:
1042:
1040:
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1026:
1012:
1011:
1000:
991:
989:
976:
975:
964:
959:
950:
941:
932:
907:348 mg/kg
899:400 mg/kg
801:
781:
773:
763:
755:
742:
706:
690:
682:racemic mixture
658:
656:Available forms
646:tobacco budworm
638:rice stem borer
619:
612:
607:
593:
580:
567:
546:
544:
542:
540:
536:
530:
513:noncombustible
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392:
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365:
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112:
101:
95:
92:
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37:
25:
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11:
5:
2338:
2336:
2328:
2327:
2322:
2317:
2312:
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2301:
2295:
2294:
2292:
2291:
2286:
2279:
2272:
2265:
2258:
2251:
2244:
2237:
2230:
2223:
2218:
2210:
2208:
2202:
2201:
2199:
2198:
2193:
2188:
2183:
2177:
2175:
2169:
2168:
2166:
2165:
2160:
2155:
2150:
2145:
2140:
2135:
2130:
2116:
2111:
2106:
2101:
2091:
2086:
2081:
2079:Hydramethylnon
2076:
2071:
2066:
2061:
2056:
2051:
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2026:
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1995:
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1927:
1909:
1904:
1899:
1894:
1889:
1884:
1879:
1874:
1869:
1864:
1859:
1854:
1849:
1844:
1839:
1834:
1829:
1824:
1819:
1814:
1809:
1803:
1801:
1795:
1794:
1792:
1791:
1786:
1781:
1776:
1771:
1766:
1761:
1756:
1751:
1746:
1741:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1701:
1696:
1691:
1686:
1681:
1676:
1671:
1666:
1661:
1656:
1651:
1646:
1641:
1636:
1631:
1626:
1621:
1616:
1611:
1606:
1601:
1596:
1591:
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1581:
1576:
1571:
1566:
1561:
1559:Chlorethoxyfos
1556:
1551:
1546:
1541:
1535:
1533:
1527:
1526:
1524:
1523:
1518:
1513:
1508:
1503:
1498:
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1478:
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1468:
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1428:
1423:
1418:
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1400:
1394:
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1375:
1370:
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1360:
1355:
1350:
1345:
1339:
1337:
1335:Neonicotinoids
1331:
1330:
1328:
1327:
1322:
1317:
1312:
1307:
1302:
1297:
1291:
1289:
1283:
1282:
1280:
1279:
1274:
1269:
1264:
1259:
1254:
1249:
1244:
1239:
1234:
1228:
1226:
1220:
1219:
1217:
1216:
1211:
1206:
1201:
1196:
1191:
1186:
1181:
1176:
1171:
1166:
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1135:
1133:
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924:
923:25 mg/kg
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917:
916:
915:30 mg/kg
913:
909:
908:
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891:45 mg/kg
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604:standard state
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583:TWA 0.5 mg/m
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2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2128:
2124:
2120:
2117:
2115:
2112:
2110:
2107:
2105:
2102:
2099:
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2092:
2090:
2087:
2085:
2082:
2080:
2077:
2075:
2072:
2070:
2067:
2065:
2062:
2060:
2057:
2055:
2052:
2050:
2047:
2045:
2044:Chlordimeform
2042:
2040:
2037:
2035:
2032:
2030:
2027:
2025:
2022:
2020:
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1300:Diflubenzuron
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988:on 2017-12-05
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579:(Recommended)
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57: –
56:
52:
51:Find sources:
45:
41:
35:
34:
29:This article
27:
23:
18:
17:
2325:Ethyl esters
2315:Insecticides
2281:
2274:
2267:
2260:
2253:
2246:
2239:
2232:
2225:
2213:
2148:Tebufenpyrad
2143:Tebufenozide
2049:Chlorfenapyr
2024:Azadirachtin
1955:Tralomethrin
1950:Tetramethrin
1892:Metofluthrin
1847:Deltamethrin
1842:Cyphenothrin
1837:Cypermethrin
1822:Bioallethrin
1769:Tebupirimfos
1674:Methidathion
1644:Fenitrothion
1569:Chlorpyrifos
1544:Azamethiphos
1506:Methoxychlor
1388:Thiamethoxam
1378:Paichongding
1363:Imidaclothiz
1358:Imidacloprid
1348:Clothianidin
1325:Pyriproxyfen
1305:Flufenoxuron
1295:Benzoylureas
1154:Butocarboxim
1123:Insecticides
1119:Pest control
1053:
1041:. Retrieved
1036:
1027:
990:. Retrieved
986:the original
951:
942:
933:
785:
777:
776:
767:
756:
743:
740:Applications
733:
726:-nitrophenol
723:
718:
714:
710:
707:
698:
691:
678:
673:
669:
665:
661:
659:
621:
620:
553:
518:
173:Identifiers
164:
160:
157:Other names
147:
143:
102:
96:October 2022
93:
83:
76:
69:
62:
50:
38:Please help
33:verification
30:
2221:Baculovirus
2173:Metabolites
2138:Sulfluramid
1940:Silafluofen
1907:Prallethrin
1887:Imiprothrin
1882:Fluvalinate
1872:Fenvalerate
1832:Cyhalothrin
1807:Acrinathrin
1799:Pyrethroids
1789:Trichlorfon
1654:Fosthiazate
1599:Dicrotophos
1383:Thiacloprid
1353:Dinotefuran
1343:Acetamiprid
1272:Paris Green
1179:Ethienocarb
1169:Carbosulfan
874:Inhalation
778:Table 1: LD
650:boll weevil
626:insecticide
533:median dose
519:Lethal dose
509:Flash point
453:Appearance
397:Properties
252:100.016.615
2304:Categories
2153:Veracevine
2084:Indoxacarb
2074:Fluralaner
2064:Fenoxycarb
2059:Fenazaquin
2054:Cyromazine
2034:Buprofezin
2014:Afoxolaner
1945:Tefluthrin
1935:Resmethrin
1902:Phenothrin
1897:Permethrin
1877:Flumethrin
1862:Etofenprox
1852:Empenthrin
1827:Cyfluthrin
1817:Bifenthrin
1812:Allethrins
1749:Quinalphos
1719:Phenthoate
1659:Isoxathion
1639:Fenamiphos
1624:Disulfoton
1619:Dioxathion
1614:Dimethoate
1594:Dichlorvos
1516:Tetradifon
1491:Heptachlor
1481:Endosulfan
1426:Cyclodiene
1373:Nithiazine
1368:Nitenpyram
1320:Methoprene
1310:Hydroprene
1237:Boric acid
1189:Isoprocarb
1184:Fenobucarb
1164:Carbofuran
1149:Bendiocarb
1131:Carbamates
992:2017-09-09
957:References
866:Wild bird
704:Metabolism
498:Insoluble
441:Molar mass
298:9Y6HP0HYA8
225:ChemSpider
201:3D model (
180:CAS Number
66:newspapers
2119:Adjuvants
2114:Sarolaner
2109:Pyriprole
2104:Pyridaben
2094:Lotilaner
2029:Bensultap
1993:Ryanodine
1930:Pyrethrum
1912:Pyrethrin
1729:Phosalone
1709:Parathion
1699:Omethoate
1679:Mevinphos
1664:Malathion
1579:Coumaphos
1554:Bensulide
1521:Toxaphene
1421:Chlordane
1315:Lufenuron
1209:Promecarb
1199:Metolcarb
1144:Aminocarb
1084:, cdc.gov
948:Treatment
795:Organism
746:acaricide
466:1.3 g/cm
190:2104-64-5
2289:Spinosad
2191:Paraoxon
2186:Malaoxon
2158:Xanthone
2133:Spinosad
2089:Limonene
2069:Fipronil
1998:Ryanodol
1970:Ryanoids
1784:Tribufos
1774:Terbufos
1759:Schradan
1649:Fenthion
1634:Ethoprop
1589:Diazinon
1539:Acephate
1476:Dieldrin
1411:Beta-HCH
1257:Cryolite
1214:Propoxur
1194:Methomyl
1159:Carbaryl
1139:Aldicarb
1043:19 March
1021:(NIOSH).
810:Chicken
753:Toxicity
642:bollworm
503:Hazards
2127:Sesamex
2019:Amitraz
1764:Temefos
1754:R-16661
1734:Phosmet
1724:Phorate
1684:Mipafox
1609:Dimefox
1501:Lindane
1471:Dicofol
1446:1,2-DCE
1441:1,1-DCE
1436:1,4-DCB
1431:1,2-DCB
1015:"#0255"
912:Rabbit
842:Pigeon
770:some LD
768:table 1
672:-ethyl
664:-ethyl
628:of the
596:5 mg/m
462:Density
265:PubChem
146:-Ethyl
80:scholar
2039:Cartap
1739:Phoxim
1629:Ethion
1496:Kepone
1486:Endrin
1406:Aldrin
1204:Oxamyl
904:Mouse
850:Quail
834:Mouse
802:value
732:. The
730:phenol
728:, and
648:, and
624:is an
446:323.30
381:SMILES
159:Ethyl
133:Names
82:
75:
68:
61:
53:
1694:Naled
1511:Mirex
1033:"EPN"
896:Duck
885:Skin
826:Duck
807:Oral
554:NIOSH
346:InChI
278:16421
234:15571
203:JSmol
87:JSTOR
73:books
2196:TCPy
2181:Oxon
1466:DFDT
1045:2015
920:Rat
888:Cat
877:Rat
858:Rat
818:Dog
590:IDLH
289:UNII
119:EPN
59:news
1461:DDT
1456:DDE
1451:DDD
1076:EPN
674:O-p
666:O-p
622:EPN
577:REL
564:PEL
315:EPA
268:CID
42:by
2306::
2125:,
1922:;
1920:II
1918:,
1121::
1035:.
1017:.
1001:^
980:.
965:^
800:50
798:LD
780:50
772:50
762:50
760:LD
652:.
644:,
640:,
636:,
529:50
527:LD
419:14
413:14
2129:)
2121:(
2100:)
2096:(
1926:)
1916:I
1914:(
1111:e
1104:t
1097:v
1047:.
995:.
734:p
724:p
719:O
715:O
711:p
670:O
662:O
535:)
531:(
434:S
431:P
428:4
425:O
422:N
416:H
410:C
317:)
313:(
205:)
165:p
161:p
148:O
144:O
109:)
103:(
98:)
94:(
84:·
77:·
70:·
63:·
36:.
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