cas 1689-84-5, Bromoxynil | Articles data

Articles about 1689-84-5Total 16 be found

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Synthesis and evaluation of heterocyclic analogues of bromoxynil
One attractive strategy to discover more active and/or crop-selective herbicides is to make structural changes to currently registered compounds. This strategy is especially appealing for those compounds with limited herbicide resistance and whose chemistry is accompanied with transgenic tools to enable herbicide tolerance in crop plants. Bromoxynil is a photosystem II (PSII) inhibitor registered for control of broadleaf weeds in several agronomic and specialty crops. Recently at the University of Tennessee - Knoxville several analogues of bromoxynil were synthesized including a previously synthesized pyridine (2,6-dibromo-5-hydroxypyridine-2-carbonitrile sodium salt), a novel pyrimidine (4,6-dibromo-5-hydroxypyrimidine-2-carbonitrile sodium salt), and a novel pyridine N-oxide (2,6-dibromo-1-oxidopyridin-1-ium-4-carbonitrile). These new analogues of bromoxynil were also evaluated for their herbicidal activity on soybean (Glycine max), cotton (Gossypium hirsutum), redroot pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), large crabgrass (Digitaria sanguinalis), and pitted morningglory (Ipomoea lacunose) when applied at 0.28 kg ha-1. A second study was conducted on a glyphosate-resistant weed (Amaranthus palmeri) with the compounds being applied at 0.56 kg ha -1. Although all compounds were believed to inhibit PSII by binding in the quinone binding pocket of D1, the pyridine and pyridine-N-oxide analogues were clearly more potent than bromoxynil on Amaranthus retroflexus. However, application of the pyrimidine herbicide resulted in the least injury to all species tested. These variations in efficacy were investigated using molecular docking simulations, which indicate that the pyridine analogue may form a stronger hydrogen bond in the pocket of the D1 protein than the original bromoxynil. A pyridine analogue was able to control the glyphosate-resistant Amaranthus palmeri with >80% efficacy. The pyridine analogues of bromoxynil showed potential to have a different weed control spectrum compared to bromoxynil. A pyridine analogue of bromoxynil synthesized in this research controlled several weed species greater than bromoxynil itself, potentially due to enhanced binding within the PSII binding pocket. Future research should compare this analogue to bromoxynil using optimized formulations at higher application rates.
Cutulle, Matthew A.,Armel, Gregory R.,Brosnan, James T.,Best, Michael D.,Kopsell, Dean A.,Bruce, Barry D.,Bostic, Heidi E.,Layton, Donovan S.
p. 329 - 336
(2014)
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A scalable and green one-minute synthesis of substituted phenols
A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols via ipso-hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and H2O2/HBr as the reagent under unprecedentedly simple and convenient conditions. A wide range of arylboronic acids were smoothly transformed into substituted phenols in very good to excellent yields without chromatographic purification. The reaction is scalable up to at least 5 grams at room temperature with one-minute reaction time and can be combined in a one-pot sequence with bromination and Pd-catalyzed cross-coupling to generate more diverse, highly substituted phenols.
Elumalai, Vijayaragavan,Hansen, J?rn H.
p. 40582 - 40587
(2020/11/18)

Intermolecular Aryl C?H Amination through Sequential Iron and Copper Catalysis
A mild, efficient and regioselective method for para-amination of activated arenes has been developed through a combination of iron and copper catalysis. A diverse range of products were obtained from an operationally simple one-pot, two-step procedure involving bromination of the aryl substrate with the powerful Lewis acid iron(III) triflimide, followed by a copper(I)-catalysed N-arylation reaction. This two-step dehydrogenative process for the regioselective coupling of aromatic C?H bonds with non-activated amines was applicable to anisole-, phenol-, aniline- and acetanilide-type aryl compounds. Importantly, the arene substrates were used as the limiting reagent and required no protecting-group manipulations during the transformation.
Mostafa, Mohamed A. B.,Calder, Ewen D. D.,Racys, Daugirdas T.,Sutherland, Andrew
supporting information
p. 1044 - 1047
(2017/02/05)

PRODRUGS OF 2-(4-(3-((4-AMINO-7-CYANO-IMIDAZO[2,1-F][1,2,4]TRIAZIN-2-YL)AMINO)PHENYL)PIPERAZ IN-1-YL)PROPANAMIDE DERIVATIVES AS CK2 INHIBITORS FOR THE TREATMENT OF CANCER
PRODRUGS OF IMIDAZOTRIAZINE COMPOUNDS AS CK2 INHIBITORS The invention provides pharmaceutically active compounds of formula (I) and prodrugs thereof. The formula (I) 2-(aminophenylamino)-4- amino-7-cyano-imidazo[2,1-f][1,2,4]triazine derivatives inhibit CK2 protein kinase activity, thereby making them useful for treating cancer, psoriasis and rheumatoid arthritis.
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(2017/05/10)

Synthesis and evaluation of heterocyclic analogues of bromoxynil
One attractive strategy to discover more active and/or crop-selective herbicides is to make structural changes to currently registered compounds. This strategy is especially appealing for those compounds with limited herbicide resistance and whose chemistry is accompanied with transgenic tools to enable herbicide tolerance in crop plants. Bromoxynil is a photosystem II (PSII) inhibitor registered for control of broadleaf weeds in several agronomic and specialty crops. Recently at the University of Tennessee-Knoxville several analogues of bromoxynil were synthesized including a previously synthesized pyridine (2,6-dibromo-5-hydroxypyridine-2-carbonitrile sodium salt), a novel pyrimidine (4,6-dibromo-5-hydroxypyrimidine-2-carbonitrile sodium salt), and a novel pyridine N-oxide (2,6-dibromo-1-oxidopyridin-1-ium-4-carbonitrile). These new analogues of bromoxynil were also evaluated for their herbicidal activity on soybean (Glycine max), cotton (Gossypium hirsutum), redroot pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), large crabgrass (Digitaria sanguinalis), and pitted morningglory (Ipomoea lacunose) when applied at 0.28 kg ha-1. A second study was conducted on a glyphosate-resistant weed (Amaranthus palmeri) with the compounds being applied at 0.56 kg ha-1. Although all compounds were believed to inhibit PSII by binding in the quinone binding pocket of D1, the pyridine and pyridine-N-oxide analogues were clearly more potent than bromoxynil on Amaranthus retroflexus. However, application of the pyrimidine herbicide resulted in the least injury to all species tested. These variations in efficacy were investigated using molecular docking simulations, which indicate that the pyridine analogue may form a stronger hydrogen bond in the pocket of the D1 protein than the original bromoxynil. A pyridine analogue was able to control the glyphosate-resistant Amaranthus palmeri with >80% efficacy. The pyridine analogues of bromoxynil showed potential to have a different weed control spectrum compared to bromoxynil. A pyridine analogue of bromoxynil synthesized in this research controlled several weed species greater than bromoxynil itself, potentially due to enhanced binding within the PSII binding pocket. Future research should compare this analogue to bromoxynil using optimized formulations at higher application rates.
Cutulle, Matthew A.,Armel, Gregory R.,Brosnan, James T.,Best, Michael D.,Kopsell, Dean A.,Bruce, Barry D.,Bostic, Heidi E.,Layton, Donovan S.
p. 329 - 336
(2015/04/22)

Cyclic aromatic analogues of the hendrickson reagent; NMR studies and electrophilic properties
Two novel cyclic aromatic analogues of the Hendrickson POP reagent, 1,1,3,3-tetraphenyl-1,3-dihydro-2,1,3-benzoxadiphosphole-1,3-diium bis(trifluoromethanesulfinate) and bis(trifluoromethanesulfonate), have been readily prepared by the treatment of 1,2-bis(diphenylphosphino)benzene or 1,2-bis(diphenylphosphoryl)benzene, respectively, with trifluoromethanesulfonic anhydride in dichloromethane. 31P and 19F NMR studies indicated that while the latter complex is formed as the sole product, the former species was shown to be the predominant component in equilibrium with 1-(diphenylphosphino)-2-[diphenyl(trifluoromethylsulfonyloxy)phosphonio]benzene trifluoromethanesulfinate and 1,2-bis[diphenyl(trifluoromethylsulfonyloxy) phosphonio]benzene bis(trifluoromethanesulfinate). The dehydrating POP systems were exploited in the conversion of aldoximes into nitriles. The dehydration occurred rapidly at room temperature and produced high yields with a variety of alkyl- and arylaldoximes, tolerating a wide range of substrates and functional groups. Georg Thieme Verlag Stuttgart New York.
Moussa, Ziad
experimental part
p. 460 - 468
(2012/03/11)

NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles
NMR Studies on the reaction of triphenylphosphine with various amounts of triflic anhydride at 0 °C is described. The reagent structure resulting from mixing 1.3 equiv of Ph3P with Tf2O (1.0 mmol) has been established as an equilibrium mixture consisting mainly of triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate and the corresponding bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate dimer. The electrophilic properties of the system have been exploited in the development of a mild method for converting aldoximes into nitriles. The dehydration occurs at 0 °C under very mild conditions by initial activation of the oxime oxygen, followed by treatment with a base and subsequent elimination of triphenylphosphine oxide. The substrate scope and functional group tolerance of this useful method are explored.
Moussa, Ziad,Ahmed, Saleh A.,ElDouhaibi, Ahmad S.,Al-Raqa, Shaya Y.
experimental part
p. 1826 - 1831
(2010/09/07)

A PROCESS FOR THE ECO-FRIENDLY PREPARATION OF 3, 5-DIBROMO-4-HYDROXYBENZONITRILE
A highly pure 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil) has been prepared in high yield from 4-hydroxybenzonitrile using eco-friendly brominating reagent comprising of 2:1 mole ratio of bromide to bromate salts in aqueous acidic medium without any catalyst under ambient conditions with no work up procedure. The product 3,5-dibromo-4-hydroxybenzonitrile was obtained in 91-99% yield with melting point 189-191°C and more than 99% purity by gas chromatographic analysis without any purification.
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(2010/09/17)

High atom efficient and environment-friendly preparation of herbicides bromoxynil and ioxynil
High atom efficient and environment-friendly preparation of herbicides bromoxynil and ioxynil using bromide/bromate and iodide/iodate couple as halogenating reagent in water at room temperature is described.
Subbarayappa, Adimurthy,Joshi, Girdhar,Patil, Rajendra D.
experimental part
p. 1678 - 1680
(2011/02/28)

Regioselective synthesis of phenols and halophenols from arylboronie acids using solid poly(N-vinylpyrrolidone)/hydrogen peroxide and poly(4-vinylpyridine) /hydrogen peroxide complexes
Solid hydrogen peroxide complexes based on poly(N-vinylpyrrolidone) and poly(4-vinylpyridine) were prepared and used as solid hydroxylating reagents. These solid hydrogen peroxide equivalents are found to be much safer, convenient and efficient reagent systems for the ipso-hydroxylation of arylboronie acids to the corresponding phenols in high yields at a faster rate. The versatility of the reagents has been further expanded for the one-pot synthesis of halophenols. Density functional theory calculations were carried out on hydrogen peroxide complexes of N-ethylpyrrolidone and 4-ethylpyridine as models to get a better understanding of structure and behavior of hydrogen peroxide complexes of the polymers poly(N-vinylpyrrolidone) and poly(4-vinylpyridine) compared to aqueous hydrogen peroxide.
Prakash, G. K. Surya,Chacko, Sujith,Panja, Chiradeep,Thomas, Tisa Elizabeth,Gurung, Laxman,Rasul, Golam,Mathew, Thomas,Olah, George A.
experimental part
p. 1567 - 1574
(2011/02/25)

Herbicidal mixtures having a synergistic effect
PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.
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(2008/06/13)

Halopyridyl triazolinone herbicides and herbicidal use thereof
Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.
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(2008/06/13)

A New Bromination Method for Phenols and Anisoles: NBS/HBF4*Et2O in CH3CN
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Oberhauser, Thomas
p. 4504 - 4506
(2007/10/03)

Substituted pyridinesulfonamide compound or its salt, process for preparing the same, and herbicide containing the same
A substituted pyridinesulfonamide compound or its salt represented by the following general formula (I): STR1 wherein A is CH or N; when A is CH, R1 and R2 may be either each independently a member selected from the group consisting of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkenyl groups, unsubstituted or substituted cycloalkyl groups, and unsubstituted or substituted phenyl groups; when A is N, R1 is an unsubstituted or substituted alkyl group, R2 is an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group; and X and Y are each independently a member selected from the group consisting of alkyl groups and alkoxy groups, is disclosed. This compound is useful as the effective ingredient of a herbicide showing a wide weed-control spectrum even if used in a small amount.
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(2008/06/13)

A novel two-step synthesis of 3,5-dibromo-4-hydroxybenzonitrile
3,5-dibromo-4-hydroxybenzonitrile, bromoxynil (III) has been synthesized in two steps from p-cresol.
Vidyasagar, A.,Nalawala, K. J.,Varshney, A. K.
p. 872 - 873
(2007/10/02)

Substituted pyridinesulfonamide compounds or their salts, process for preparing the same, and herbicides containing the same
A substituted pyridinesulfonamide compound or its salt represented by the following general formula (I): wherein R1 is an unsubstituted or substituted alkyl group; R2 is an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group; and X and Y are each independently a member selected from the group consisting of alkyl groups and alkoxy groups, is disclosed. This compound is useful as the effective ingredient of a herbicide showing a wide weed-control spectrum even if used in a small amount.
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(2008/06/13)

Process for preparing benzonitriles
The invention relates to a process for the preparation of a compound of formula I STR1 R is alkyl, and X is bromine or iodine which process comprises: reacting a compound of formula II in a two phase system, said system comprising an aqueous phase and an organic phase comprising a water immiscible solvent, with an acylating agent of formula III or IV in the presence of a base catalyst. STR2
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(2008/06/13)