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36:
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of pesticides. Firstly, before a formulated product can be developed for market, the active substance must be approved for the
European Union. After this has been achieved, authorisation for the specific product must be sought from every Member State that the applicant wants to sell it to.
632:
543:
Bifenox is not currently used in the United States although in 1981 it had been subject to a full regulatory review, under the then-new "Registration
Standard" process. Within the European Union, a 2-tiered approach is used for the
519:: 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
100:
479:(as its sodium salt with brand name Blazer) in 1980. Both compounds had much improved properties including a wider spectrum of herbicidal effect and good safety to some crops, including
511:
The detailed mechanism of action for nitrofen, acifluorfen and related diphenyl ether herbicides was unknown at the time they were invented. The effects visible on whole plants are
899:
Dayan, Franck E.; Reddy, Krishna N.; Duke, Stephen O. (1999). "Structure-Activity
Relationships of Diphenyl Ethers and Other Oxygen-Bridged Protoporphyrinogen Oxidase Inhibitors".
785:, Bayer H. O.; Swithenbank C. & Yih R. Y., "Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers", issued 1975-12-23, assigned to Rohm & Haas
545:
415:
1290:
257:
1010:
916:
766:, Theissen R.J., "Substituted Phenoxybenzoic Acids and Esters thereof", issued 1974-01-08, assigned to Mobil Oil Corporation
722:
560:
Bifenox is normally applied postemergence (when weeds are visible in the crop). It controls or suppresses a wide range of species including
1078:
2012:
2002:
1976:
1438:
553:. Bifenox is registered for use against weeds in crops including cereals, soybeans, sugarbeet and rice. In Switzerland, some of its
232:
663:
1403:
686:
550:
932:
549:
Afterwards, there is a monitoring programme to make sure the pesticide residues in food are below the limits set by the
175:
35:
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2007:
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979:"Conclusion regarding the peer review of the pesticide risk assessment of the active substance bifenox"
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48:
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66:
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and first registered for sale in 1964. This area of chemistry became very competitive, with the
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InChI=1S/C14H9Cl2NO5/c1-21-14(18)10-7-9(3-4-12(10)17(19)20)22-13-5-2-8(15)6-11(13)16/h2-7H,1H3
1833:
1732:
499:
The preparation of bifenox first described in the Mobil patent includes as its final step an
990:
904:
871:
863:
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574:
451:
The nitrophenyl ethers are a well-known class of herbicides, the oldest member of which was
430:
422:
349:
280:
184:
120:
76:
1588:
608:. The product is typically used at application rates of 720 g a.i. per hectare.
528:
503:
between the potassium salt of 2,4-dichlorophenol and methyl 2-nitro-5-chlorobenzoic acid.
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142:
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705:
Nagano, Eiki (1999). "Herbicidal
Efficacy of Protoporphyrinogen Oxidase Inhibitors".
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group adjacent to the nitro group of nitrofen. Bifenox was launched with the
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535:. Both light and oxygen are required for this process to kill the plant.
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Mowdown in 1981. Meanwhile Rohm & Haas had patented and developed
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Except where otherwise noted, data are given for materials in their
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26:
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1801:
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648:. Vol. 2. Fresno, CA: Thomson Publications. p. 15.
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filing in 1969 and grant in 1974 of a patent to the
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660:"Compendium of Pesticide Common Names: bifenox"
75:
265:COC(=O)C1=C(C=CC(=C1)OC2=C(C=C(C=C2)Cl)Cl)(=O)
53:Methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate
1072:
852:"Interaction of Chloroplasts with Inhibitors"
8:
633:Institute for Occupational Safety and Health
1053:in the Pesticide Properties DataBase (PPDB)
758:
756:
1806:
1720:
1679:
1536:
1453:
1391:
1079:
1065:
1057:
827:"Bifenox: Pesticide Registration Standard"
677:Kwesi Ampong-Nyarko, Surajit K. De Datta.
216:
141:
119:
18:
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183:
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617:
262:
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821:
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495:Final step in the synthesis of bifenox
132:
16:Chemical compound used as an herbicide
527:in the plant cells. This is a potent
343:85 °C (185 °F; 358 K)
244:Key: SUSRORUBZHMPCO-UHFFFAOYSA-N
7:
523:, which leads to an accumulation of
679:A Handbook for Weed Control in Rice
557:can be used in lawns and orchards.
531:which activates oxygen, leading to
154:
14:
304:
298:
292:
34:
25:
956:Pesticide Properties Database.
801:Pesticide Properties Database.
738:Pesticide Properties Database.
396:(at 25 °C , 100 kPa).
551:European Food Safety Authority
307:
286:
1:
1020:. August 2019. Archived from
960:. University of Hertfordshire
805:. University of Hertfordshire
742:. University of Hertfordshire
715:10.1007/978-3-642-58633-0_11
909:10.1007/978-3-642-58633-0_5
368:or concentration (LD, LC):
2029:
850:Ridley, Stuart M. (1983).
546:approval and authorisation
521:protoporphyrinogen oxidase
434:protoporphyrinogen oxidase
2013:Chlorobenzene derivatives
1811:Photosystem II inhibitors
1725:Photosystem II inhibitors
629:GESTIS Substance Database
390:
364:
359:
273:
253:
228:
59:
47:
42:
33:
24:
2003:Nitrobenzene derivatives
1684:Photosystem I inhibitors
996:10.2903/j.efsa.2008.119r
937:pubchem.ncbi.nlm.nih.gov
901:Peroxidizing Herbicides
707:Peroxidizing Herbicides
563:Capsella bursa-pastoris
461:Mobil Oil Corporation's
436:which is necessary for
386:6400 mg/kg (oral, rat)
646:Agricultural Chemicals
644:Thomson, W.T. (1977).
496:
783:US patent 3928416
764:US patent 3784635
494:
431:inhibiting the enzyme
903:. pp. 141–161.
832:. EPA. December 1981
803:"Acifluorfen-sodium"
709:. pp. 293–302.
593:Veronica hederifolia
501:Ullmann condensation
49:Preferred IUPAC name
1912:aminocyclopyrachlor
1877:sulfometuron methyl
868:10.1104/pp.72.2.461
507:Mechanism of action
350:Solubility in water
325: g·mol
21:
1872:metsulfuron-methyl
1541:Nitrophenyl ethers
533:lipid peroxidation
497:
400:Infobox references
19:
1985:
1984:
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1532:Protox inhibitors
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1449:ACCase inhibitors
1011:"Fox: MAPP 11981"
989:(2): 119r. 2008.
918:978-3-642-63674-5
724:978-3-642-63674-5
581:Myosotis arvensis
525:protoporphyrin IX
465:structural analog
408:Chemical compound
406:
405:
197:CompTox Dashboard
101:Interactive image
2020:
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575:Lamium purpureum
457:Rohm & Haas
423:organic compound
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933:"Bifenox: Uses"
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681:. p. 68.
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1972:pyribenzoxim
1967:prosulfocarb
1957:metam sodium
1819:chlortoluron
1602:saflufenacil
1553:
1304:isoxaflutole
1213:aminopyralid
1177:pretilachlor
1147:dimethenamid
1142:diflufenican
1088:Pest control
1048:
1029:. Retrieved
1022:the original
1017:
1005:
986:
983:EFSA Journal
982:
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962:. Retrieved
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555:formulations
542:
510:
498:
467:with a COOCH
450:
411:
410:
365:
60:Identifiers
1844:tebuthiuron
1839:monolinuron
1597:butafenacil
1579:oxyfluorfen
1559:fluorodifen
1549:acifluorfen
1466:chlorazifop
1414:dichlorprop
1367:glufosinate
1329:sulcotrione
1238:pyrithiobac
1192:trifluralin
1162:metolachlor
1157:metazachlor
1127:benfluralin
517:desiccation
477:acifluorfen
438:chlorophyll
425:used as an
419:common name
380:median dose
366:Lethal dose
330:Appearance
274:Properties
139:100.050.795
1992:Categories
1962:metribuzin
1942:indaziflam
1922:bromoxynil
1882:tribenuron
1788:metamitron
1748:hexazinone
1675:Quaternary
1650:fluroxypyr
1514:sethoxydim
1496:quizalofop
1481:fenoxaprop
1377:piperophos
1372:glyphosate
1324:sethoxydim
1319:nitisinone
1314:mesotrione
1258:Arsenicals
1243:quinclorac
1223:clopyralid
1218:chloramben
1182:propachlor
1112:acetochlor
1092:herbicides
1031:2021-03-08
964:2021-03-08
942:2021-03-08
836:2021-03-07
809:2021-03-03
746:2021-03-03
740:"Nitrofen"
688:9712200205
612:References
473:brand name
355:0.35 mg/L
318:Molar mass
185:KSB85XT26Y
112:ChemSpider
88:3D model (
77:42576-02-3
67:CAS Number
1952:methazole
1927:clomazone
1907:aclonifen
1783:terbutryn
1763:propazine
1758:prometryn
1743:cyanazine
1716:Triazines
1692:cyperquat
1665:triclopyr
1660:thiazopyr
1645:dithiopyr
1637:Pyridines
1564:fomesafen
1491:haloxyfop
1486:fluazifop
1471:cyhalofop
1352:bialaphos
1347:bensulide
1248:quinmerac
1137:diethatyl
1132:butachlor
1018:Adama.com
958:"Bifenox"
513:chlorosis
487:Synthesis
441:synthesis
427:herbicide
1917:Bentazon
1773:simetryn
1768:simazine
1753:prometon
1738:atrazine
1702:paraquat
1655:imazapyr
1574:nitrofen
1569:lactofen
1476:diclofop
1434:mecoprop
1419:fenoprop
1362:fosamine
1357:ethephon
1233:picloram
1202:Aromatic
1187:propanil
1167:oryzalin
1152:flamprop
1117:alachlor
1104:anilines
1100:Anilides
886:16663025
453:nitrofen
360:Hazards
20:Bifenox
1947:juglone
1937:dinoseb
1834:monuron
1829:linuron
1733:ametryn
1554:bifenox
1439:2,4,5-T
1387:Phenoxy
1228:dicamba
1050:Bifenox
877:1066256
631:of the
627:in the
625:Record
481:soybean
447:History
421:for an
414:is the
412:Bifenox
152:PubChem
1895:Others
1697:diquat
1409:2,4-DB
1396:Auxins
1122:asulam
915:
884:
874:
789:
770:
721:
685:
323:342.13
258:SMILES
43:Names
1977:Ziram
1802:Ureas
1404:2,4-D
1205:acids
1025:(PDF)
1014:(PDF)
830:(PDF)
233:InChI
165:39230
121:35891
90:JSmol
1932:DCBN
1902:3-AT
1824:DCMU
1429:MCPB
1424:MCPA
1281:MSMA
1276:DSMA
913:ISBN
882:PMID
719:ISBN
683:ISBN
664:BCPC
602:and
539:Uses
515:and
176:UNII
991:doi
905:doi
872:PMC
864:doi
711:doi
416:ISO
202:EPA
155:CID
1994::
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376:50
374:LD
299:Cl
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311:5
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200:(
92:)
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