768:(FQPA) and the Pesticide Registration Improvement Act (PRIA). A pesticide can only be used legally according to the directions on the label that is included at the time of the sale of the pesticide. The purpose of the label is "to provide clear directions for effective product performance while minimizing risks to human health and the environment". A label is a legally binding document that mandates how the pesticide can and must be used and failure to follow the label as written when using the pesticide is a federal offence.
33:
339:
245:
24:
701:
1265:
1202:
1246:
670:
Mowdown in 1981. Meanwhile Rohm & Haas introduced acifluorfen (as its sodium salt with brand name Blazer) in 1980, having developed it under the code number RH-6201. It had much improved properties including a wider spectrum of herbicidal effect and good safety to soybean crops. The first patent
991:
The estimated annual use of acifluorfen in US agriculture is mapped by the US Geological
Service and shows that as of 2018 approximately 550,000 pounds (250,000 kg) were applied — mainly in soybean. The compound is not registered for use in the
1263:, Bayer H. O.; Swithenbank C. & Yih R. Y., "Nouveaux ethers 4-trifluoromethyl-4'-nitro-diphenyliques herbicides et leur application a la lutte contre les mauvaises herbes", issued 1973-09-13, assigned to Rohm & Haas
771:
Acifluorfen sodium is normally applied postemergence (when weeds are visible in the crop). It controls or suppresses broadleaf weeds, grasses and sedges and is effective on a very wide range of species including
728:: several hypotheses were advanced regarding the molecular-level interactions which might explain these symptoms. The now-accepted explanation for the damage is that these compounds inhibit the enzyme
547:
1089:
Andrews, Christopher J.; Skipsey, Mark; Townson, Jane K.; Morris, Carol; Jepson, Ian; Edwards, Robert (1997). "Glutathione transferase activities toward herbicides used selectively in soybean".
1328:
Dayan, Franck E.; Reddy, Krishna N.; Duke, Stephen O. (1999). "Structure-Activity
Relationships of Diphenyl Ethers and Other Oxygen-Bridged Protoporphyrinogen Oxidase Inhibitors".
130:
761:
1244:, Bayer H. O.; Swithenbank C. & Yih R. Y., "Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers", issued 1975-12-23, assigned to Rohm & Haas
582:
1730:
1141:
757:
388:
1447:
753:
671:
for the material was published in
December 1975, although an earlier Belgian patent published in September 1973 had described related chemistry.
1200:, Theissen R.J., "Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers", issued 1974-01-08, assigned to Mobil Oil Corporation
1378:
1345:
1518:
2457:
1108:
372:
Na salt: InChI=1S/C14H7ClF3NO5.Na/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21;/h1-6H,(H,20,21);/q;+1/p-1
2447:
2416:
1878:
353:
1009:
1398:
1075:
532:
1843:
286:
765:
316:
2114:
1720:
1008:
In
California, acifluorfen is listed as "known to the state to cause cancer or reproductive toxicity" according to
729:
600:
566:
509:
1778:
1091:
834:
623:
1162:
2371:
1715:
1511:
1133:
2437:
798:
786:
679:
The preparation of acifluorfen first described in the Rohm & Haas patent includes as its final steps an
240:
2442:
2341:
1394:
1028:
924:
900:
888:
362:
InChI=1S/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21)
172:
2452:
2293:
936:
496:
1241:
1197:
1738:
1260:
930:
858:
780:
774:
680:
45:
683:
between 2-chloro-4-trifluoromethylphenol and 2-nitro-5-fluorobenzonitrile. The intermediate is then
2351:
2316:
2057:
1710:
1504:
984:
334:
86:
1616:
32:
2311:
1768:
1677:
1596:
942:
870:
864:
840:
792:
741:
1816:
650:
and first registered for sale in 1964. This area of chemistry became very competitive, with the
2222:
2202:
2197:
2099:
1687:
1576:
2212:
1888:
1826:
1801:
1591:
1374:
1341:
1310:
1112:
1100:
972:
966:
954:
918:
906:
876:
852:
846:
822:
810:
733:
655:
2273:
2172:
1366:
1333:
1300:
1292:
1104:
948:
912:
688:
642:
The nitrophenyl ethers are a well-known class of herbicides, the oldest member of which was
634:
and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice.
597:
589:
485:
411:
304:
296:
201:
193:
105:
97:
2028:
988:. The product is typically used at application rates of 0.375 lb a.i. per acre.
978:
894:
828:
737:
1488:
1176:
338:
244:
1071:
1050:
151:
2250:
2217:
2164:
1705:
1468:
1305:
1280:
1217:
993:
960:
816:
804:
631:
607:
560:
700:
23:
2431:
2306:
2301:
2123:
2062:
1971:
1945:
1897:
1748:
1611:
1361:
Nagano, Eiki (1999). "Herbicidal
Efficacy of Protoporphyrinogen Oxidase Inhibitors".
647:
474:
233:
720:
was unknown at the time they were invented. The effects visible on whole plants are
2411:
2406:
2396:
2258:
2041:
1743:
1652:
1644:
1586:
1581:
1527:
585:
275:
267:
1370:
2283:
2278:
2036:
2018:
1998:
1980:
1905:
1853:
1806:
1641:
1631:
1601:
1566:
1337:
725:
692:
604:
2401:
2381:
2361:
2321:
2227:
2187:
2089:
1953:
1935:
1920:
1811:
1763:
1758:
1753:
1682:
1662:
1657:
1621:
1551:
684:
667:
619:
451:
183:
1116:
2391:
2366:
2346:
2182:
2104:
2084:
2003:
1930:
1925:
1910:
1791:
1786:
1571:
1531:
882:
721:
717:
593:
1496:
1314:
2356:
2207:
2192:
2177:
2155:
2141:
2094:
2076:
2013:
2008:
1915:
1873:
1858:
1796:
1672:
1626:
1606:
1556:
1109:
10.1002/(sici)1096-9063(199710)51:2<213::aid-ps622>3.0.co;2-l
1021:
744:. Both light and oxygen are required for this process to kill the plant.
713:
643:
212:
1423:
1296:
222:
2386:
2376:
2268:
1993:
1697:
1667:
1543:
1539:
997:
663:
611:
464:
253:
2136:
1848:
1561:
162:
559:
Except where otherwise noted, data are given for materials in their
2131:
1835:
1025:
651:
615:
141:
129:
118:
2263:
2241:
1868:
1863:
1500:
1134:"Registration Review Label Mitigation for Sodium Acifluorfen"
662:
group adjacent to the nitro group of nitrofen. This product,
716:, acifluorfen and related diphenyl ether herbicides such as
321:
541:
760:(EPA) is responsible for regulating pesticides under the
614:
naturally have a high tolerance to acifluorfen and its
396:
Acid: Clc2cc(ccc2Oc1cc(C(=O)O)c(()=O)cc1)C(F)(F)F
654:
filing in 1969 and grant in 1974 of a patent to the
2334:
2292:
2249:
2240:
2163:
2154:
2122:
2113:
2075:
2050:
2027:
1979:
1970:
1944:
1896:
1887:
1834:
1825:
1777:
1729:
1696:
1640:
1538:
1072:"Compendium of Pesticide Common Names: acifluorfen"
762:
1448:"Estimated Agricultural Use for Acifluorfen, 2018"
996:, although a closely related nitrophenyl ether,
274:
266:
104:
96:
1128:
1126:
1512:
1281:"Interaction of Chloroplasts with Inhibitors"
1142:United States Environmental Protection Agency
8:
1236:
1234:
2246:
2160:
2119:
1976:
1893:
1831:
1519:
1505:
1497:
1417:
1415:
337:
243:
200:
192:
15:
1304:
303:
295:
1041:
393:
358:
333:
221:
234:
736:in the plant cells. This is a potent
712:The detailed mechanism of action for
375:Key: RVULBHWZFCBODE-UHFFFAOYSA-M
365:Key: NUFNQYOELLVIPL-UHFFFAOYSA-N
171:
150:
7:
732:, which leads to an accumulation of
1446:US Geological Survey (2021-10-12).
740:which activates oxygen, leading to
256:
14:
699:
438:
432:
429:
423:
31:
22:
1467:Pesticide Properties Database.
1422:United Phosphorus, Inc (2012).
1216:Pesticide Properties Database.
1175:Pesticide Properties Database.
1049:Pesticide Properties Database.
758:Environmental Protection Agency
563:(at 25 °C , 100 kPa).
1395:"About Pesticide Registration"
1165:, Extension Toxicology Network
441:
417:
77:: Acifluorfen sodium
1:
1471:. University of Hertfordshire
1220:. University of Hertfordshire
1179:. University of Hertfordshire
1053:. University of Hertfordshire
1371:10.1007/978-3-642-58633-0_11
1338:10.1007/978-3-642-58633-0_5
766:Food Quality Protection Act
630:. It is effective against
2474:
1279:Ridley, Stuart M. (1983).
1031:also used as an herbicide.
730:protoporphyrinogen oxidase
601:protoporphyrinogen oxidase
2458:Trifluoromethyl compounds
2251:Photosystem II inhibitors
2165:Photosystem II inhibitors
835:Cardiospermum halicacabum
557:
526:
404:
384:
349:
61:
56:
44:
39:
30:
21:
2448:Nitrobenzene derivatives
2124:Photosystem I inhibitors
1424:"Ultra Blazer herbicide"
666:, was launched with the
1489:The Proposition 65 List
1363:Peroxidizing Herbicides
1330:Peroxidizing Herbicides
799:Ambrosia artemisiifolia
787:Acanthospermum hispidum
652:Mobil Oil Corporation's
603:which is necessary for
71:: Acifluorfen
1000:, is available there.
925:Melochia corchorifolia
901:Euphorbia heterophylla
889:Echinochloa crus-galli
50:5--2-nitrobenzoic acid
1242:US patent 3928416
1198:US patent 3784635
937:Polygonum convolvulus
598:inhibiting the enzyme
491:250 g/L (20 °C)
1365:. pp. 293–302.
1332:. pp. 141–161.
1261:BE patent 796677
1218:"Acifluorfen-sodium"
931:Mollugo verticillata
859:Convolvulus arvensis
781:Acalypha ostryifolia
775:Abutilon theophrasti
681:Ullmann condensation
46:Preferred IUPAC name
2352:aminocyclopyrachlor
2317:sulfometuron methyl
1297:10.1104/pp.72.2.461
985:Xanthium strumarium
708:Mechanism of action
486:Solubility in water
459: g·mol
18:
2312:metsulfuron-methyl
1981:Nitrophenyl ethers
1401:. 27 February 2013
943:Portulaca oleracea
871:Cyperus esculentus
865:Croton glandulosus
841:Cassia obtusifolia
793:Amaranthus palmeri
742:lipid peroxidation
620:metabolic disposal
567:Infobox references
504:1.18 (20 °C)
76:
70:
16:
2425:
2424:
2330:
2329:
2236:
2235:
2150:
2149:
2071:
2070:
1972:Protox inhibitors
1966:
1965:
1962:
1961:
1889:ACCase inhibitors
1380:978-3-642-63674-5
1347:978-3-642-63674-5
1092:Pesticide Science
973:Sorghum halepense
967:Solanum rostratum
955:Sesbania exaltata
919:Ipomoea quamoclit
907:Helianthus annuus
877:Datura stramonium
853:Citrullus lanatus
847:Chenopodium album
823:Calystegia sepium
811:Barbarea vulgaris
734:protoporphyrin IX
656:structural analog
575:Chemical compound
573:
572:
545:
317:CompTox Dashboard
131:Interactive image
74:
68:
2465:
2247:
2161:
2120:
2029:Pyrimidinediones
1977:
1894:
1832:
1779:Organophosphorus
1521:
1514:
1507:
1498:
1491:
1486:
1480:
1479:
1477:
1476:
1464:
1458:
1457:
1455:
1454:
1443:
1437:
1436:
1434:
1433:
1428:
1419:
1410:
1409:
1407:
1406:
1391:
1385:
1384:
1358:
1352:
1351:
1325:
1319:
1318:
1308:
1285:Plant Physiology
1276:
1270:
1269:
1268:
1264:
1257:
1251:
1250:
1249:
1245:
1238:
1229:
1228:
1226:
1225:
1213:
1207:
1206:
1205:
1201:
1194:
1188:
1187:
1185:
1184:
1172:
1166:
1160:
1154:
1153:
1151:
1150:
1138:
1130:
1121:
1120:
1086:
1080:
1079:
1068:
1062:
1061:
1059:
1058:
1046:
949:Richardia scabra
913:Hibiscus trionum
703:
689:hydrobromic acid
648:Rohm & Haas
590:organic compound
543:
540:
458:
443:
440:
434:
431:
425:
419:
412:Chemical formula
342:
341:
325:
323:
307:
299:
278:
270:
258:
247:
236:
225:
204:
196:
175:
154:
133:
108:
100:
35:
26:
19:
2473:
2472:
2468:
2467:
2466:
2464:
2463:
2462:
2428:
2427:
2426:
2421:
2326:
2288:
2232:
2146:
2109:
2067:
2046:
2023:
1958:
1940:
1883:
1821:
1773:
1739:flurochloridone
1725:
1711:copper arsenate
1692:
1636:
1534:
1525:
1495:
1494:
1487:
1483:
1474:
1472:
1466:
1465:
1461:
1452:
1450:
1445:
1444:
1440:
1431:
1429:
1426:
1421:
1420:
1413:
1404:
1402:
1393:
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1388:
1381:
1360:
1359:
1355:
1348:
1327:
1326:
1322:
1278:
1277:
1273:
1266:
1259:
1258:
1254:
1247:
1240:
1239:
1232:
1223:
1221:
1215:
1214:
1210:
1203:
1196:
1195:
1191:
1182:
1180:
1174:
1173:
1169:
1161:
1157:
1148:
1146:
1136:
1132:
1131:
1124:
1088:
1087:
1083:
1070:
1069:
1065:
1056:
1054:
1048:
1047:
1043:
1038:
1018:
1006:
979:Striga asiatica
895:Eleusine indica
829:Cannabis sativa
750:
738:photosensitizer
710:
677:
661:
640:
632:broadleaf weeds
576:
569:
564:
553:
518:
488:
456:
446:
437:
428:
422:
414:
400:
397:
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391:
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326:
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259:
228:
207:
178:
157:
136:
122:
111:
89:
80:
52:
51:
12:
11:
5:
2471:
2469:
2461:
2460:
2455:
2450:
2445:
2440:
2438:PPO herbicides
2430:
2429:
2423:
2422:
2420:
2419:
2414:
2409:
2404:
2399:
2394:
2389:
2384:
2379:
2374:
2369:
2364:
2359:
2354:
2349:
2344:
2338:
2336:
2332:
2331:
2328:
2327:
2325:
2324:
2319:
2314:
2309:
2304:
2298:
2296:
2294:ALS inhibitors
2290:
2289:
2287:
2286:
2281:
2276:
2271:
2266:
2261:
2255:
2253:
2244:
2238:
2237:
2234:
2233:
2231:
2230:
2225:
2220:
2218:terbuthylazine
2215:
2210:
2205:
2200:
2195:
2190:
2185:
2180:
2175:
2169:
2167:
2158:
2152:
2151:
2148:
2147:
2145:
2144:
2139:
2134:
2128:
2126:
2117:
2111:
2110:
2108:
2107:
2102:
2097:
2092:
2087:
2081:
2079:
2073:
2072:
2069:
2068:
2066:
2065:
2060:
2054:
2052:
2048:
2047:
2045:
2044:
2039:
2033:
2031:
2025:
2024:
2022:
2021:
2016:
2011:
2006:
2001:
1996:
1991:
1985:
1983:
1974:
1968:
1967:
1964:
1963:
1960:
1959:
1957:
1956:
1950:
1948:
1946:DIM herbicides
1942:
1941:
1939:
1938:
1933:
1928:
1923:
1918:
1913:
1908:
1902:
1900:
1898:FOP herbicides
1891:
1885:
1884:
1882:
1881:
1876:
1871:
1866:
1861:
1856:
1851:
1846:
1840:
1838:
1829:
1823:
1822:
1820:
1819:
1814:
1809:
1804:
1799:
1794:
1789:
1783:
1781:
1775:
1774:
1772:
1771:
1766:
1761:
1756:
1751:
1746:
1741:
1735:
1733:
1731:HPPD inhbitors
1727:
1726:
1724:
1723:
1718:
1713:
1708:
1706:cacodylic acid
1702:
1700:
1694:
1693:
1691:
1690:
1685:
1680:
1675:
1670:
1665:
1660:
1655:
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1535:
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1524:
1523:
1516:
1509:
1501:
1493:
1492:
1481:
1459:
1438:
1411:
1386:
1379:
1353:
1346:
1320:
1291:(2): 461–468.
1271:
1252:
1230:
1208:
1189:
1167:
1155:
1122:
1081:
1063:
1040:
1039:
1037:
1034:
1033:
1032:
1017:
1014:
1010:Proposition 65
1005:
1002:
994:European Union
961:Setaria faberi
817:Brassica kaber
805:Anoda cristata
749:
746:
709:
706:
705:
704:
676:
673:
659:
646:, invented by
639:
636:
574:
571:
570:
565:
561:standard state
558:
555:
554:
552:
551:
537:
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352:
351:
350:
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343:
329:
327:
315:
312:
311:
309:
308:
302:Na salt:
300:
291:
289:
283:
282:
280:
279:
273:Na salt:
271:
262:
260:
252:
249:
248:
238:
230:
229:
227:
226:
217:
215:
209:
208:
206:
205:
199:Na salt:
197:
188:
186:
180:
179:
177:
176:
167:
165:
159:
158:
156:
155:
146:
144:
138:
137:
135:
134:
125:
123:
116:
113:
112:
110:
109:
103:Na salt:
101:
92:
90:
85:
82:
81:
79:
78:
72:
66:
62:
59:
58:
54:
53:
49:
48:
42:
41:
37:
36:
28:
27:
13:
10:
9:
6:
4:
3:
2:
2470:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2443:Benzoic acids
2441:
2439:
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1051:"Acifluorfen"
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2453:Chloroarenes
2412:pyribenzoxim
2407:prosulfocarb
2397:metam sodium
2259:chlortoluron
2042:saflufenacil
1988:
1744:isoxaflutole
1653:aminopyralid
1617:pretilachlor
1587:dimethenamid
1582:diflufenican
1528:Pest control
1484:
1473:. Retrieved
1462:
1451:. Retrieved
1441:
1430:. Retrieved
1403:. Retrieved
1389:
1362:
1356:
1329:
1323:
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1284:
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1222:. Retrieved
1211:
1192:
1181:. Retrieved
1170:
1158:
1147:. Retrieved
1145:. 2020-06-02
1140:
1096:
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1084:
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1055:. Retrieved
1044:
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695:as solvent.
678:
658:with a COOCH
641:
628:-transferase
625:
624:glutathione
578:
577:
533:Legal status
513:
498:
173:ChEMBL222440
57:Identifiers
17:Acifluorfen
2284:tebuthiuron
2279:monolinuron
2037:butafenacil
2019:oxyfluorfen
1999:fluorodifen
1989:acifluorfen
1906:chlorazifop
1854:dichlorprop
1807:glufosinate
1769:sulcotrione
1678:pyrithiobac
1632:trifluralin
1602:metolachlor
1597:metazachlor
1567:benfluralin
1163:Acifluorfen
1103:: 213–222.
726:desiccation
693:acetic acid
605:chlorophyll
592:used as an
586:common name
579:Acifluorfen
469:1.573 g/mL
405:Properties
332:Acid:
294:Acid:
265:Acid:
241:100.051.468
220:Acid:
191:Acid:
170:Acid:
152:CHEBI:73172
149:Acid:
128:Acid:
95:Acid:
2432:Categories
2402:metribuzin
2382:indaziflam
2362:bromoxynil
2322:tribenuron
2228:metamitron
2188:hexazinone
2115:Quaternary
2090:fluroxypyr
1954:sethoxydim
1936:quizalofop
1921:fenoxaprop
1817:piperophos
1812:glyphosate
1764:sethoxydim
1759:nitisinone
1754:mesotrione
1698:Arsenicals
1683:quinclorac
1663:clopyralid
1658:chloramben
1622:propachlor
1552:acetochlor
1532:herbicides
1475:2021-03-03
1453:2023-12-13
1432:2021-03-06
1405:2021-02-27
1224:2021-03-03
1183:2021-03-03
1177:"Nitrofen"
1149:2021-03-05
1057:2021-03-03
1036:References
1029:derivative
685:hydrolysed
668:brand name
452:Molar mass
305:6H07I1G902
297:OI60IB203A
184:ChemSpider
117:3D model (
106:62476-59-9
98:50594-66-6
87:CAS Number
2392:methazole
2367:clomazone
2347:aclonifen
2223:terbutryn
2203:propazine
2198:prometryn
2183:cyanazine
2156:Triazines
2132:cyperquat
2105:triclopyr
2100:thiazopyr
2085:dithiopyr
2077:Pyridines
2004:fomesafen
1931:haloxyfop
1926:fluazifop
1911:cyhalofop
1792:bialaphos
1787:bensulide
1688:quinmerac
1577:diethatyl
1572:butachlor
1469:"Bifenox"
1117:0031-613X
883:Digitaria
722:chlorosis
718:fomesafen
675:Synthesis
608:synthesis
594:herbicide
65:Compounds
2357:Bentazon
2213:simetryn
2208:simazine
2193:prometon
2178:atrazine
2142:paraquat
2095:imazapyr
2014:nitrofen
2009:lactofen
1916:diclofop
1874:mecoprop
1859:fenoprop
1802:fosamine
1797:ethephon
1673:picloram
1642:Aromatic
1627:propanil
1607:oryzalin
1592:flamprop
1557:alachlor
1544:anilines
1540:Anilides
1315:16663025
1022:Lactofen
1016:See also
714:nitrofen
644:nitrofen
612:Soybeans
550:(Poison)
213:DrugBank
2387:juglone
2377:dinoseb
2274:monuron
2269:linuron
2173:ametryn
1994:bifenox
1879:2,4,5-T
1827:Phenoxy
1668:dicamba
1306:1066256
998:bifenox
752:In the
664:bifenox
638:History
588:for an
581:is the
510:Acidity
479:155 °C
465:Density
254:PubChem
223:DB07338
75:Na salt
2335:Others
2137:diquat
1849:2,4-DB
1836:Auxins
1562:asulam
1399:US EPA
1377:
1344:
1313:
1303:
1267:
1248:
1204:
1115:
1004:Safety
756:, the
687:using
618:, via
546:
457:361.66
389:SMILES
163:ChEMBL
40:Names
2417:Ziram
2242:Ureas
1844:2,4-D
1645:acids
1427:(PDF)
1137:(PDF)
1101:Wiley
1099:(2).
1026:ester
1024:, an
748:Usage
616:salts
522:3.86
354:InChI
276:44072
268:44073
202:40112
194:40113
142:ChEBI
119:JSmol
2372:DCBN
2342:3-AT
2264:DCMU
1869:MCPB
1864:MCPA
1721:MSMA
1716:DSMA
1375:ISBN
1342:ISBN
1311:PMID
1113:ISSN
1076:BCPC
982:and
724:and
497:log
287:UNII
69:Acid
1367:doi
1334:doi
1301:PMC
1293:doi
1105:doi
691:in
622:by
583:ISO
322:EPA
257:CID
2434::
1530::
1414:^
1397:.
1373:.
1340:.
1309:.
1299:.
1289:72
1287:.
1283:.
1233:^
1139:.
1125:^
1111:.
1097:51
1095:.
1074:.
1012:.
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970:,
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940:,
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910:,
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898:,
892:,
886:,
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874:,
868:,
862:,
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850:,
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778:,
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548:S6
542:AU
519:)
512:(p
430:Cl
421:14
1542:/
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1227:.
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660:3
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517:a
514:K
499:P
445:5
442:O
439:N
436:3
433:F
427:7
424:H
418:C
324:)
320:(
121:)
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