270:
177:
506:
501:
511:
734:
774:
722:
710:
24:
1219:
1156:
1197:
852:. Before a formulated product can be developed for market, the active substance must be approved. Then authorisation for the specific product must be sought from every Member State that the applicant wants to sell it to. Afterwards, there is a monitoring programme to make sure the pesticide residues in food are below the limits set by the
1066:
Kahlau, Sabine; Schröder, Florian; Freigang, Jörg; Laber, Bernd; Lange, Gudrun; Passon, Daniel; Kleeßen, Sabrina; Lohse, Marc; Schulz, Arno; von
Koskull-Döring, Pascal; Klie, Sebastian; Gille, Sascha (October 2020). "Aclonifen targets solanesyl diphosphate synthase, representing a novel mode of
703:, was launched in 1981. Meanwhile, Rohm & Haas introduced acifluorfen (as its sodium salt) in 1980. It had much improved properties including a wider spectrum of herbicidal effect and good safety to soybean crops. The first patent for this material was published in December 1975,
748:
compounds having an amine group adjacent to the nitro substituent and also having an additional chlorine atom between the amine and the oxygen of the diphenyl ether. 2-Chloro-3-phenoxy-6-nitroaniline was described as having selectivity, so that important
663:(PPO). Both mechanisms could result in the observed whole-plant effect of bleaching (removal of leaf colour) and the compound includes chemical features (a nitro group attached to a diphenyl ether) that are known to result in PPO effects, as seen with
837:
668:
871:
according to the crop and formulation. For example, Proclus is used in winter wheat and
Emerger in potatoes. It is normally applied pre-emergence (before weeds are visible in the crop) and controls or suppresses species including
519:
481:
805:: in 1983 several hypotheses were advanced regarding the molecular-level interactions which might explain these symptoms. By 1992, it was becoming clear that most compounds of this class inhibit the enzyme
465:
836:. This led to the conclusion that it expressed a dual mode of action. In 2020, further research revealed that it is likely to have a completely different and novel mode of action, targeting
1336:
Dayan, Franck E.; Reddy, Krishna N.; Duke, Stephen O. (1999). "Structure-Activity
Relationships of Diphenyl Ethers and Other Oxygen-Bridged Protoporphyrinogen Oxidase Inhibitors".
1217:, Buck W.; Linden G. & Lust S. et al., "2-Chloro-3-(phenoxy or phenylthio)-6-6-nitro-anilines", issued 1981-09-16, assigned to Celamerck GmbH and Co KG
972:
Kılınç, Özgür; Reynaud, Stéphane; Perez, Laurent; Tissut, Michel; Ravanel, Patrick (February 2009). "Physiological and biochemical modes of action of the diphenylether aclonifen".
1309:
Nandihalli, Ujjana B.; Duke, Mary V.; Duke, Stephen O. (1992). "Quantitative structure-activity relationships of protoporphyrinogen oxidase-inhibiting diphenyl ether herbicides".
860:
is registered for use against weeds in crops including cereals, potato and sunflower. It is particularly safe to sunflower, owing to the metabolism which occurs in that crop.
797:
The detailed mechanism of action for nitro diphenyl ether herbicides such as acifluorfen was unknown at the time they were invented. The effects visible on whole plants are
94:
1195:, Bayer H. O.; Swithenbank C. & Yih R. Y., "Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers", issued 1975-12-23, assigned to Rohm & Haas
849:
1876:
309:
744:
Celamerck scientists were also working on analogs retaining the 4-nitrodiphenyl ether framework and in 1978 filed a patent of relatively narrow scope which
1233:
Matringe, M.; Clair, D.; Scalla, R. (1990). "Effects of peroxidizing herbicides on protoporphyrin IX levels in non-chlorophyllous soybean cell culture".
1495:
Kılınç, Özgür; Grasset, Renaud; Reynaud, Stéphane (June 2011). "The herbicide aclonifen: The complex theoretical bases of sunflower tolerance".
1154:, Theissen R.J., "Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers", issued 1974-01-08, assigned to Mobil Oil Corporation
1386:
1353:
1664:
1111:
2588:
2562:
2024:
1002:
Dayan, Franck E; Owens, Daniel K; Duke, Stephen O (2012-01-09). "Rationale for a natural products approach to herbicide discovery".
284:
781:
The preparation of aclonifen first described in
Celamerck patents starts from 2,3,4-trichloronitrobenzene. This is reacted in an
450:
1989:
853:
581:
565:
1013:
555:
227:
601:
510:
505:
573:
248:
667:, for example. In 2020, further research revealed that aclonifen has a different and novel mode of action, targeting
500:
2260:
1866:
829:
806:
660:
632:
427:
1924:
184:
1606:
2517:
1861:
1657:
955:
1004:
593:
172:
2603:
2487:
874:
733:
134:
1464:"Conclusion regarding the peer review of the pesticide risk assessment of the active substance aclonifen"
2598:
2439:
1524:"Efficacy and selectivity of pre-emergent sunflower herbicides under different soil moisture conditions"
533:
493:
414:
36:
785:
with ammonia in dimethyl sulfoxide. The intermediate aniline is treated with potassium phenolate in an
1214:
1192:
1151:
1884:
892:
786:
547:
2583:
2497:
2462:
2203:
1856:
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1555:
840:. This has led to its being classified in its own group for the purposes of resistance management.
265:
60:
1762:
1436:
2457:
1914:
1823:
1742:
1092:
1045:
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569:
1962:
687:
and first registered for sale in 1964. This area of chemistry became very competitive, with the
2368:
2348:
2343:
2245:
1833:
1722:
848:
Aclonifen is registered for use in the
European Union, where a two-tiered approach is used for
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1972:
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981:
762:
679:
The nitrophenyl ethers are a well-known class of herbicides, the oldest member of which was
403:
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2117:
2091:
2043:
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1757:
1420:
1403:
1369:
Nagano, Eiki (1999). "Herbicidal
Efficacy of Protoporphyrinogen Oxidase Inhibitors".
1322:
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684:
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165:
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InChI=1S/C12H9ClN2O3/c13-11-10(18-8-4-2-1-3-5-8)7-6-9(12(11)14)15(16)17/h1-7H,14H2
216:
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915:
in 2017, aclonifen began to be used as a pre-emergence herbicide in potatoes.
825:
656:
369:
145:
1480:
1463:
1033:
824:
Aclonifen was shown to be an inhibitor of PPO but in addition had effects on
2537:
2512:
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2149:
2076:
2071:
2056:
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2019:
2004:
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1702:
821:. Both light and oxygen are required for this process to kill the plant.
680:
1277:
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2522:
2414:
2139:
1843:
1813:
1689:
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758:
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382:
203:
185:
23:
2282:
1994:
1707:
655:
has been uncertain, with evidence suggesting it might interfere with
125:
1080:
1025:
908:
when used at application rates of 600 g a.i. per hectare.
625:
Except where otherwise noted, data are given for materials in their
2277:
1522:
Jursík, M.; Soukup, J.; Holec, J.; Andr, J.; Hamouzová, K. (2016).
1981:
772:
688:
105:
93:
83:
609:
2409:
2387:
2014:
2009:
765:
under the code number RPA099795 and launched in 1983 in Europe.
613:
1646:
699:
group adjacent to the nitro group of nitrofen. This product,
1408:
Turkish
Journal of Agriculture - Food Science and Technology
253:
757:
crops and this lack of damage to the crop extended to some
459:
1404:"The Symptoms of Herbicidal Action: The Case of Aclonifen"
651:
which has been used in agriculture since the 1980s. Its
761:. Aclonifen was subsequently developed and marketed by
691:
filing in 1969 and grant in 1974 of a patent to the
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2438:
2395:
2386:
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2300:
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2221:
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2125:
2116:
2090:
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1980:
1971:
1923:
1875:
1842:
1786:
1684:
997:
995:
215:
69:
1435:Weed Science Society of America (April 2021).
1658:
1262:"Interaction of Chloroplasts with Inhibitors"
1112:"The growing problem of pesticide resistance"
8:
1209:
1207:
1639:in the Pesticide Properties DataBase (PPDB)
397:81.2 °C (178.2 °F; 354.3 K)
2392:
2306:
2265:
2122:
2039:
1977:
1665:
1651:
1643:
268:
175:
153:
15:
1539:
1479:
1419:
1285:
1061:
1059:
967:
965:
809:(PPO), which leads to an accumulation of
235:
1607:"New herbicide to help replace linuron"
1605:Cunningham, Charlotte (12 April 2019).
924:
911:In the UK, following the withdrawal of
705:
314:
289:
264:
934:
932:
930:
928:
317:C1=CC=C(C=C1)OC2=C(C(=C(C=C2)(=O))N)Cl
166:
1497:Pesticide Biochemistry and Physiology
1311:Pesticide Biochemistry and Physiology
1235:Pesticide Biochemistry and Physiology
974:Pesticide Biochemistry and Physiology
813:in the plant cells. This is a potent
296:Key: DDBMQDADIHOWIC-UHFFFAOYSA-N
133:
113:
7:
817:which activates oxygen, leading to
659:biosynthesis or inhibit the enzyme
206:
671:which would also cause bleaching.
14:
753:weeds could be controlled within
40:2-chloro-6-nitro-3-phenoxyaniline
1421:10.24925/turjaf.v3i6.472-477.391
732:
720:
708:
509:
504:
499:
353:
350:
344:
22:
1402:Kılınç, Özgür Kıvılcım (2015).
1170:Pesticide Properties Database.
1129:Pesticide Properties Database.
939:Pesticide Properties Database.
789:using acetonitrile as solvent.
629:(at 25 °C , 100 kPa).
943:. University of Hertfordshire.
854:European Food Safety Authority
838:solanesyl diphosphate synthase
669:solanesyl diphosphate synthase
359:
338:
1:
1437:"HRAC Mode of Action Updates"
1174:. University of Hertfordshire
1133:. University of Hertfordshire
1110:Pinho, Bárbara (2021-04-06).
863:Aclonifen is now supplied by
1509:10.1016/j.pestbp.2011.04.001
1379:10.1007/978-3-642-58633-0_11
1323:10.1016/0048-3575(92)90033-V
1247:10.1016/0048-3575(90)90039-5
1014:Society of Chemical Industry
986:10.1016/j.pestbp.2008.11.008
828:synthesis, by inhibition of
1346:10.1007/978-3-642-58633-0_5
2620:
1260:Ridley, Stuart M. (1983).
850:approval and authorisation
832:at similar concentrations
807:protoporphyrinogen oxidase
777:The synthesis of aclonifen
661:protoporphyrinogen oxidase
2397:Photosystem II inhibitors
2311:Photosystem II inhibitors
623:
480:
475:
444:
325:
305:
280:
53:
45:
35:
30:
21:
2589:Nitrobenzene derivatives
2270:Photosystem I inhibitors
1611:Crop Production Magazine
1528:Plant Protection Science
1481:10.2903/j.efsa.2008.149r
1067:action for herbicides".
556:Precautionary statements
1585:cropscience.bayer.co.uk
1560:cropscience.bayer.co.uk
1371:Peroxidizing Herbicides
1338:Peroxidizing Herbicides
1069:Pest Management Science
1005:Pest Management Science
787:Ullmann ether synthesis
689:Mobil Oil Corporation's
875:Alopecurus myosuroides
778:
409:1.4 mg/L (20 °C)
1215:US patent 4394159
1193:US patent 3928416
1152:US patent 3784635
776:
1541:10.17221/82/2014-PPS
1373:. pp. 293–302.
1340:. pp. 141–161.
1172:"Acifluorfen-sodium"
893:Fallopia convolvulus
647:is a diphenyl ether
2498:aminocyclopyrachlor
2463:sulfometuron methyl
1278:10.1104/pp.72.2.461
867:under a variety of
830:phytoene desaturase
793:Mechanism of action
404:Solubility in water
377: g·mol
18:
2458:metsulfuron-methyl
2127:Nitrophenyl ethers
954:PubChem Database.
865:Bayer Crop Science
819:lipid peroxidation
779:
633:Infobox references
16:
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2475:
2382:
2381:
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2217:
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2118:Protox inhibitors
2112:
2111:
2108:
2107:
2035:ACCase inhibitors
1388:978-3-642-63674-5
1355:978-3-642-63674-5
1075:(10): 3377–3388.
887:Chenopodium album
858:active ingredient
811:protoporphyrin IX
693:structural analog
641:Chemical compound
639:
638:
534:Hazard statements
463:
249:CompTox Dashboard
95:Interactive image
2611:
2393:
2307:
2266:
2175:Pyrimidinediones
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1978:
1925:Organophosphorus
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1266:Plant Physiology
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1967:
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1885:flurochloridone
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1857:copper arsenate
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881:Anthemis cotula
846:
815:photosensitizer
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1629:External links
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1534:(4): 214–222.
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1503:(2): 193–198.
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1317:(3): 193–211.
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1241:(3): 300–307.
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991:
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167:ECHA InfoCard
164:
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144:
143:
136:
135:ChEMBL1485557
132:
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29:
25:
20:
2599:Chloroarenes
2558:pyribenzoxim
2553:prosulfocarb
2543:metam sodium
2492:
2405:chlortoluron
2188:saflufenacil
1890:isoxaflutole
1799:aminopyralid
1763:pretilachlor
1733:dimethenamid
1728:diflufenican
1674:Pest control
1634:
1614:. Retrieved
1610:
1600:
1589:. Retrieved
1584:
1575:
1564:. Retrieved
1559:
1550:
1531:
1527:
1517:
1500:
1496:
1490:
1474:(10). 2008.
1471:
1468:EFSA Journal
1467:
1458:
1447:. Retrieved
1443:
1430:
1411:
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1397:
1370:
1364:
1337:
1331:
1314:
1310:
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1265:
1255:
1238:
1234:
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1176:. Retrieved
1165:
1146:
1135:. Retrieved
1124:
1115:
1105:
1072:
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1009:
1003:
980:(2): 65–71.
977:
973:
949:
910:
903:
897:
891:
885:
879:
873:
862:
847:
833:
823:
796:
780:
743:
695:with a COOCH
678:
644:
643:
525:
482:
451:Legal status
431:
416:
115:CHEBI:137374
54:Identifiers
46:Other names
2430:tebuthiuron
2425:monolinuron
2183:butafenacil
2165:oxyfluorfen
2145:fluorodifen
2135:acifluorfen
2052:chlorazifop
2000:dichlorprop
1953:glufosinate
1915:sulcotrione
1824:pyrithiobac
1778:trifluralin
1748:metolachlor
1743:metazachlor
1713:benfluralin
956:"Aclonifen"
941:"Aclonifen"
869:brand names
803:desiccation
739:Acifluorfen
665:acifluorfen
520:Signal word
326:Properties
173:100.070.619
2584:Herbicides
2578:Categories
2548:metribuzin
2528:indaziflam
2508:bromoxynil
2468:tribenuron
2374:metamitron
2334:hexazinone
2261:Quaternary
2236:fluroxypyr
2100:sethoxydim
2082:quizalofop
2067:fenoxaprop
1963:piperophos
1958:glyphosate
1910:sethoxydim
1905:nitisinone
1900:mesotrione
1844:Arsenicals
1829:quinclorac
1809:clopyralid
1804:chloramben
1768:propachlor
1698:acetochlor
1678:herbicides
1591:2021-05-10
1566:2021-05-10
1449:2021-05-10
1414:(6): 472.
1178:2021-03-03
1137:2021-03-03
1131:"Nitrofen"
919:References
826:carotenoid
657:carotenoid
494:Pictograms
387:1.46 g/cm
370:Molar mass
237:1762RDA835
146:ChemSpider
82:3D model (
71:74070-46-5
61:CAS Number
37:IUPAC name
17:Aclonifen
2538:methazole
2513:clomazone
2493:aclonifen
2369:terbutryn
2349:propazine
2344:prometryn
2329:cyanazine
2302:Triazines
2278:cyperquat
2251:triclopyr
2246:thiazopyr
2231:dithiopyr
2223:Pyridines
2150:fomesafen
2077:haloxyfop
2072:fluazifop
2057:cyhalofop
1938:bialaphos
1933:bensulide
1834:quinmerac
1723:diethatyl
1718:butachlor
1636:Aclonifen
1581:"Emerger"
1556:"Proclus"
1097:211063448
1034:1526-498X
799:chlorosis
783:autoclave
769:Synthesis
649:herbicide
645:Aclonifen
602:P333+P313
594:P308+P313
590:P302+P352
485:labelling
194:277-704-1
186:EC Number
48:RPA099795
2594:Anilines
2503:Bentazon
2359:simetryn
2354:simazine
2339:prometon
2324:atrazine
2288:paraquat
2241:imazapyr
2160:nitrofen
2155:lactofen
2062:diclofop
2020:mecoprop
2005:fenoprop
1948:fosamine
1943:ethephon
1819:picloram
1788:Aromatic
1773:propanil
1753:oryzalin
1738:flamprop
1703:alachlor
1690:anilines
1686:Anilides
1444:wssa.net
1296:16663025
1089:32034864
1050:10841777
1042:22232033
834:in vitro
715:Nitrofen
681:nitrofen
476:Hazards
468:(Poison)
2533:juglone
2523:dinoseb
2420:monuron
2415:linuron
2319:ametryn
2140:bifenox
2025:2,4,5-T
1973:Phenoxy
1814:dicamba
1287:1066256
913:linuron
759:cereals
746:claimed
727:Bifenox
701:bifenox
675:History
526:Warning
428:Acidity
383:Density
204:PubChem
2481:Others
2283:diquat
1995:2,4-DB
1982:Auxins
1708:asulam
1587:. 2019
1562:. 2020
1385:
1352:
1294:
1284:
1221:
1199:
1158:
1095:
1087:
1048:
1040:
1032:
856:. The
464:
440:-3.15
375:264.67
310:SMILES
126:ChEMBL
31:Names
2563:Ziram
2388:Ureas
1990:2,4-D
1791:acids
1616:3 May
1440:(PDF)
1093:S2CID
1046:S2CID
1018:Wiley
1012:(4).
755:dicot
751:grass
422:4.37
285:InChI
217:92389
155:83411
106:ChEBI
84:JSmol
2518:DCBN
2488:3-AT
2410:DCMU
2015:MCPB
2010:MCPA
1867:MSMA
1862:DSMA
1618:2021
1383:ISBN
1350:ISBN
1292:PMID
1085:PMID
1038:PMID
1030:ISSN
902:and
844:Uses
801:and
618:P501
614:P405
610:P391
606:P363
598:P321
586:P281
582:P280
578:P273
574:P272
570:P261
566:P202
562:P201
548:H410
544:H351
540:H317
415:log
228:UNII
1536:doi
1505:doi
1501:100
1476:doi
1416:doi
1375:doi
1342:doi
1319:doi
1282:PMC
1274:doi
1243:doi
1077:doi
1022:doi
982:doi
483:GHS
254:EPA
207:CID
2580::
1676::
1609:.
1583:.
1558:.
1532:51
1530:.
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1470:.
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Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
