Abstracts
Quinoxyfen
CAS No. 124495-18-7
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ACTIVITY: Fungicide (unclassified)

CAS Name: 5,7-dichloro-4-(4-fluorophenoxy)quinoline

Structure:


http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15212264

Environ Sci Technol. 2004 May 15;38(10):2885-93.

Pesticide volatilization from plants: improvement of the PEC model PELMO based on a boundary-layer concept.

Wolters A, Leistra M, Linnemann V, Klein M, Schaffer A, Vereecken H.

Forschungszentrum Julich GmbH, Institute of Chemistry and Dynamics of the Geosphere IV: Agrosphere, 52425 Julich, Germany. a.wolters@fz-juelich.de

Calculation of pesticide volatilization from plants as an integral component of pesticide fate models is of utmost importance, especially as part of PEC (predicted environmental concentrations) models used in the registration procedures for pesticides. A mechanistic approach using a laminar air-boundary layer concept to predict volatilization from plant surfaces was compared to data obtained in a wind-tunnel study after simultaneous application of parathion-methyl, fenpropimorph, and quinoxyfen to winter wheat. Parathion-methyl was shown to have the highest volatilization during the wind-tunnel study of 10 days (29.2%). Volatilization of quinoxyfen was about 15.0%, revealing a higher volatilization tendency than fenpropimorph (6.0%), which is attributed to enhanced penetration of fenpropimorph counteracting volatilization. Predictions of the boundary-layer approach were markedly influenced by the selected values for the equivalent thickness of the boundary layer and rate coefficients, thus indicating that future improvements of the approach will require a deeper understanding of the kinetics of the underlying processes, e.g. phototransformation and penetration. The boundary-layer volatilization module was included in the European registration model PELMO, enabling simultaneous calculation of volatilization from plants and soil. Application of PELMO to experimental findings were the first comprehensive PEC model calculations to imply the relevant processes affecting the postapplication fate of pesticides.

PMID: 15212264 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12568578&dopt=Abstract

J Agric Food Chem 2003 Feb 12;51(4):1090-4

Influence of Different Mineral and Organic Pesticide Treatments on Cd(II), Cu(II), Pb(II), and Zn(II) Contents Determined by Derivative Potentiometric Stripping Analysis in Italian White and Red Wines.

Salvo F, La Pera L, Di Bella G, Nicotina M, Dugo G.

Dipartimento di Chimica Organica e Biologica, University of Messina, Salita Sperone 31, 98166 Messina, Italy, and Dipartimento di Entomologia e Zoologia Agraria, University of Napoli, Via Universita 100, 80055 Napoli, Italy.

This paper deals with the use of derivative potentiometric stripping analysis (dPSA) as a rapid and precise method to determine Cd(II), Cu(II), Pb(II), and Zn(II) levels in red and white wine samples from Sicily, Campania, and Tuscany and to investigate the possible connection between the content of these metals and the pesticide treatments used in vine-growing to control plant diseases and pests. dPSA allowed direct quantitation of heavy metals in acidified wines without any sample pretreatment. Mean recoveries of Cd(II), Cu(II), Pb(II), and Zn(II) ranged from 95.5 to 99.2% for white wine samples and from 96.1 to 100.0% for red wine samples. The obtained results showed that Cd(II) was not found in any sample and that Cu(II), Pb(II), and Zn(II) levels were always lower than the toxicity limits in both fungicide- and water-treated wines. Nevertheless, the contents of metals were increased in samples from organic and inorganic pesticides treatment with respect to the water-treated samples. In particular, quinoxyfen, dinocap-penconazole, and dinocap applications considerably increased Cu(II) and Zn(II) contents in white and red wines. The levels of lead were significantly raised by azoxystrobin and sulfur treatments.

PMID: 12568578 [PubMed - in process]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11553131&dopt=Abstract

Contact Dermatitis 2001 Aug;45(2):119-20

No abstract available

Occupational allergic contact dermatitis caused by 5,7-dichloro-4-(4-fluorophenoxy)quinoline (quinoxyfen).

Chowdhury MM, Chakrabarti A, Prais L, Foulds IS.

Birmingham Skin Centre, Dudley Road, Birmingham B18 7QH, UK.

PMID: 11553131 [PubMed - in process]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12233191&dopt=Abstract

Pest Manag Sci 2002 Sep;58(9):972-4

Quinoxyfen--resistance management and sensitivity monitoring in wheat: 1995-2000.

Bernhard U, Leader A, Longhurst C, Felsenstein FG.

Dow AgroSciences GmbH, Truderinger Str. 15, 81677 Munich, Germany.

Wheat powdery mildew, Blumeria (= Erysiphe) graminis DC f sp tritici Marschal is one of the most important foliar diseases of cereals in Europe, and has shown a high potential for adaptability in sensitivity towards modern fungicides during the last 20 years. Quinoxyfen is a surface-mobile fungicide from a new chemical class that has been commercially used for the control of B graminis in Europe since 1997. When the compound was launched, a Resistance Management Strategy was implemented which included: no seed treatments, no autumn use, a specified window of application and recommendations for appropriate tank-mixing. To assess the success of this Management Strategy, a European-wide resistance monitoring programme was carried out between 1995 and 2000 using spore trap sampling, and a whole plant assay. The mean EC50 values found by year were 0.060 mg litre-1 in 1995, 0.052 mg litre-1 in 1996, 0.071 ml litre-1 in 1997, 0.039 mg litre-1 in 1998, 0.039 mg litre-1 in 1999 and 0.063 mg litre-1 in 2000. No new sensitivity classes were found. The slight shift to lower sensitivity in 1998 and 1999 was correlated with similar shifts in three wildtype isolates, and was ascribed to experimental variation. The monitoring programme will continue to assess the long-term impact of the management recommendations on the resistance status of quinoxyfen.

PMID: 12233191 [PubMed - in process]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12033804&dopt=Abstract

J Agric Food Chem 2002 Jun 5;50(12):3412-8

Erratum in: J Agric Food Chem 2002 Jul 17;50(15):4430

Method development and fate determination of pesticide-treated hops and their subsequent usage in the production of beer.

Hengel MJ, Shibamoto T.

University of California, Davis, One Shields Avenue, Davis, California 95616, USA. mjhengel@ucdavis.edu

The fate of residues of seven agrochemicals (chlorfenapyr, quinoxyfen, tebuconazole, fenarimol, pyridaben, and E- and Z-dimethomorph) from the treatment on hops to the brewing of beer was studied. First, a multi-residue analytical method was developed for the determination of pesticide residues in spent hops, trub, wort, and beer. Each matrix was validated over at least two levels of fortification, for all seven compounds, in the ranges 0.05-5.0, 0.001-1.0, 0.001-0.05, and 0.0005-1.0 ppm for spent hops, trub, wort, and beer, respectively. Recoveries ranged from 73 to 136%. Second, the matrixes prepared from hops, which were treated under commercial practices with each compound, were analyzed using the method developed. The use of treated hops resulted in the carryover of 0.001 ppm of tebuconazole, 0.008 Z-dimethomorph, and 0.005 ppm of E-dimethomorph into the wort. The bulk of the remaining residues of all seven compounds was found on the spent hops. Following fermentation, all compounds were found in levels less than 0.0005 ppm in beer, except Z- (0.006 ppm) and E-dimethomorph (0.004 ppm). Third, when all seven pesticides were spiked prior to the pitching of yeast into clean wort, most of the nonpolar compounds (chlorfenapyr, quinoxyfen, and pyridaben) partitioned into the organic material (trub) which settled to the bottom, while the more polar compounds (fenarimol, tebuconazole, and E- and Z-dimethomorph) were generally distributed evenly between the beer and the trub.


PMID: 12033804 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11312786&dopt=Abstract

J Agric Food Chem 2000 Dec;48(12):6128-31

Fate of quinoxyfen residues in grapes, wine, and their processing products.

Cabras P, Angioni A, Garau VL, Pirisi FM, Cabitza F, Pala M, Farris GA.

Dipartimento di Tossicologia, Universita di Cagliari, via Ospedale 72, 09124 Cagliari, Italy. pcabras@unica.it

Quinoxyfen is a new fungicide that belongs to the family of the quinolines, recently introduced to control powdery mildew (Uncinula necator). In this paper the fate of quinoxyfen residues from vine to wine and in their processing products was studied. After the last of four applications at the recommended rate, 0.38 mg/kg of residue was found on the grapes, which is under the legal limit fixed in Italy (0.5 mg/kg). The degradation rate was according to a pseudo-first-order kinetics (r = 0.964) and the half-life was 7.24 days. Vinification was carried out with and without maceration. During the vinifications without maceration <50% of the residues passed from the grapes to the musts. Separation of the lees (8%) from the must by centrifugation caused no detectable residues in centrifuged must. At the end of fermentation with and without maceration no quinoxyfen residues were determinable in the wine. No effect on the alcoholic or malolactic fermentation was observed even in the presence of higher quinoxyfen concentrations than those found in the grapes at harvest time. During fermentation, the yeasts partially degraded the pesticides and completly adsorbed them. Bacteria, on the other hand, do not have any degradative effect on the pesticides. The raisins obtained by sun-drying did not contain any residues, whereas those obtained by oven-drying show the same amount of residues as in the fresh grapes. During the sun-drying process the fruit weight decreased by a factor of 4; the decrease in the oven-drying was equivalent. Samples of dregs and liquid lees, fortified with high levels of quinoxyfen. were double-distilled. The first dregs distillate, with an alcohol content of 32.1%, did not show any residues, whereas the first lees distillate, with an alcohol content of 34.5%, showed 7% of the initial residues. After the second lees distillation, the obtained product showed an alcoholic content of 81.2% and no residues of quinoxyfen (<0.01 mg/kg).


PMID: 11312786 [PubMed - indexed for MEDLINE]


From Toxline at Toxnet

PESTICIDE SCIENCE; 51 (3). 1997. 347-351.

Defining the resistance risk of the new powdery mildew fungicide quinoxyfen.

HOLLOMON DW, WHEELER I, DIXON K, LONGHURST C, SKYLAKAKIS G

IACR-Long Ashton Res. Stn., Dep. Agric. Sci., Univ. Bristol, Long Ashton, Bristol BS18 9AF, UK.

BIOSIS COPYRIGHT: BIOL ABS. The new powdery mildew fungicide quinoxyfen belongs to the novel quinoline class of chemistry. Although its biochemical mode of action is unknown, quinoxyfen does not act in the same way as other cereal fungicides. It is a systemic protectant which inhibits the early stages of mildew infection on a wide range of crops, and provides season-long protection from a single early-season spray applied around GS 31. The base-line sensitivity profile of quinoxyfen was defined for barley powdery mildew (Erysiphe graminis f. sp. hordei) from over 340 field isolates collected from different parts of the UK from 1991 onwards. Sensitivities ranged from <0.001 - 0.16 mg litre-1 with a mean of 0.003 mg litre-1. Current work is extending the base-line sensitivity studies to wheat powdery mildew (E. graminis f.sp. tritici), and includes isolates from European trials, but so far this new data set has shown no differences from barley powdery mildew. Quinoxyfen-resistant mutants were ge [abstract truncated]


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