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Acifluorfen

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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
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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".
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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
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In California, acifluorfen is listed as "known to the state to cause cancer or reproductive toxicity" according to
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The preparation of acifluorfen first described in the Rohm & Haas patent includes as its final steps an
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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)
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between 2-chloro-4-trifluoromethylphenol and 2-nitro-5-fluorobenzonitrile. The intermediate is then
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and first registered for sale in 1964. This area of chemistry became very competitive, with the
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The nitrophenyl ethers are a well-known class of herbicides, the oldest member of which was
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and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice.
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Nagano, Eiki (1999). "Herbicidal Efficacy of Protoporphyrinogen Oxidase Inhibitors".
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was unknown at the time they were invented. The effects visible on whole plants are
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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
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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
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Acid: Clc2cc(ccc2Oc1cc(C(=O)O)c(()=O)cc1)C(F)(F)F
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filing in 1969 and grant in 1974 of a patent to the
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Federal Insecticide, Fungicide, and Rodenticide Act
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: 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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: 1649: 1647: 1638: 1637: 1635: 1634: 1629: 1624: 1619: 1614: 1609: 1604: 1599: 1594: 1589: 1584: 1579: 1574: 1569: 1564: 1559: 1554: 1548: 1546: 1536: 1535: 1526: 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: 535: 529: 528: 524: 523: 520: 516: 506: 505: 502: 493: 492: 489: 484: 481: 480: 477: 471: 470: 467: 461: 460: 454: 448: 447: 444: 435: 426: 420: 415: 410: 407: 406: 402: 401: 399: 398: 395: 387: 386: 385: 382: 381: 379: 378: 374: 371: 370: 368: 364: 361: 360: 352: 351: 350: 347: 346: 344: 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: 2436: 2435: 2433: 2418: 2415: 2413: 2410: 2408: 2405: 2403: 2400: 2398: 2395: 2393: 2390: 2388: 2385: 2383: 2380: 2378: 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the 763: 759: 755: 754:United States 747: 745: 743: 739: 735: 731: 727: 723: 719: 715: 707: 702: 698: 697: 696: 694: 690: 686: 682: 674: 672: 669: 665: 657: 653: 649: 645: 637: 635: 633: 629: 627: 621: 617: 613: 609: 606: 602: 599: 596:. It acts by 595: 591: 587: 584: 580: 568: 562: 556: 549: 539: 538: 536: 534: 531: 530: 527:Pharmacology 525: 521: 515: 511: 508: 507: 503: 501: 500: 495: 494: 490: 487: 483: 482: 478: 476: 475:Melting point 473: 472: 468: 466: 463: 462: 455: 453: 450: 449: 416: 413: 409: 408: 403: 394: 390: 383: 369: 359: 355: 348: 340: 336: 335:DTXSID0020022 331: 330: 328: 318: 314: 313: 306: 301: 298: 293: 292: 290: 288: 285: 284: 277: 272: 269: 264: 263: 261: 255: 251: 250: 246: 242: 239: 237: 235:ECHA InfoCard 232: 231: 224: 219: 218: 216: 214: 211: 210: 203: 198: 195: 190: 189: 187: 185: 182: 181: 174: 169: 168: 166: 164: 161: 160: 153: 148: 147: 145: 143: 140: 139: 132: 127: 126: 124: 120: 115: 114: 107: 102: 99: 94: 93: 91: 88: 84: 83: 73: 67: 64: 63: 60: 55: 47: 43: 38: 34: 29: 25: 20: 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: 1288: 1284: 1274: 1255: 1222:. Retrieved 1211: 1192: 1181:. Retrieved 1170: 1158: 1147:. Retrieved 1145:. 2020-06-02 1140: 1096: 1090: 1084: 1066: 1055:. Retrieved 1044: 1007: 990: 983: 977: 971: 965: 959: 953: 947: 941: 935: 929: 923: 917: 911: 905: 899: 893: 887: 881: 875: 869: 863: 857: 851: 845: 839: 833: 827: 821: 815: 809: 803: 797: 791: 785: 779: 773: 770: 751: 711: 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:. 976:, 970:, 964:, 958:, 952:, 946:, 940:, 934:, 928:, 922:, 916:, 910:, 904:, 898:, 892:, 886:, 880:, 874:, 868:, 862:, 856:, 850:, 844:, 838:, 832:, 826:, 820:, 814:, 808:, 802:, 796:, 790:, 784:, 778:, 610:. 548:S6 542:AU 519:) 512:(p 430:Cl 421:14 1542:/ 1520:e 1513:t 1506:v 1478:. 1456:. 1435:. 1408:. 1383:. 1369:: 1350:. 1336:: 1317:. 1295:: 1227:. 1186:. 1152:. 1119:. 1107:: 1078:. 1060:. 660:3 626:S 544:: 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:)

Index

Skeletal formula
Space-filling model of acifluorfen
Preferred IUPAC name
CAS Number
50594-66-6
62476-59-9
JSmol
Interactive image
ChEBI
CHEBI:73172
ChEMBL
ChEMBL222440
ChemSpider
40113
40112
DrugBank
DB07338
ECHA InfoCard
100.051.468
Edit this at Wikidata
PubChem
44073
44072
UNII
OI60IB203A
6H07I1G902
CompTox Dashboard
DTXSID0020022
Edit this at Wikidata
InChI

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