text:
There are described a method for enriching the anabolic p-hydroxyphenylpyruvate dioxygenases from plant tissues and a method by means of which the enzymatic activity of the enzyme can be measured in a simple manner without complete purification of the enzyme being necessary.
The invention furthermore describes an assay system for identifying inhibitors of p-hydroxyphenylpyruvate dioxygenase from plants, in which an enriched HPPD from plants is incubated with a test substrate to be examined and the enzymatic activity of the enzyme is determined in comparison with the activity of the uninhibited enzyme.
The invention furthermore describes the novel herbicidal active substances of the formula (I) ##STR1## which were found using the assay method according to the invention.
1. A p-hydroxyphenylpyruvate dioxygenase inhibitor identified by the general formula (I) ##STR212## wherein: R1 is Cl,
R2 is H,
R3 is methylsulfonyl, and
Q is 2,4-dichloro-6-hydroxyphenyl.
2. A herbicidal composition containing a p-hydroxyphenylpyruvate dioxygenase inhibitor as claimed in claim 1.
This application is a division of application Ser. No. 08/369,875, filed on Jan. 6, 1995, which in turn is a continuation of application Ser. No. 08/200,741 filed on Feb. 23, 1994, now abandoned.
p-Hydroxyphenylpyruvate dioxygenase (HPPD; p-hydroxyphenylpyruvate: oxygen oxidoreductase, EC 22.214.171.124) in plant tissues is an enzyme central to the biosynthesis of the quinoid- compounds derived from the amino acid tyrosine, such as plastoguinones or tocopherols. During the biosynthesis of quinone, tyrosine is first transaminated by a transaminase to give p-hydroxyphenylpyruvate, which is then decarboxylated and hydroxylated by the enzyme HPPD in a complex sequence. The product of this reaction is homogentisic acid. These first two steps of quinone biosynthesis can analogously also be detected in animal tissues and microorganisms. While, in plants, the homogentisic acid formed can be reacted to give plastoquinones and tocopherols, however, it is an intermediate in the catabolism of the amino acid tyrosine in animals and microorganisms. Plastoquinones and tocopherols are essential structures for plants. Inhibitors of the biosynthesis of plastoquinones and tocopherols should therefore be potential herbicides.
Catabolic p-hydroxyphenylpyruvate dioxygenases have previously been purified and characterized from animal tissues (Lindstedt, S. and Odelhog, B. (1987) Meth. Enzymol. 142, 139-142) and microorganisms (Lindstedt, S. and Odelhog, B. (1987) Meth. Enzymol. 142, 143-148). (Anabolic) p-hydroxyphenylpyruvate dioxygenases from plants, in contrast, have been described in the literature (Fiedler, E., Soll, J. and Schultz, G. (1982) Planta 155, 511-515), but no method for enriching the enzyme has been described to date.
Specifically, there has been no information to date in the literature on simple methods of measuring the plant enzyme which, of course, are indispensible for purification of the enzyme and detecting inhibitors of the enzyme.
The method described by Fiedler et al. is relatively complicated and does not allow the quantitative assays to be carried out which are required for identifying potential herbicides.
What follows describes a method for enriching the anabolic p-hydroxyphenylpyruvate dioxygenases from plant tissues and a method by means of which the enzymatic activity of the enzyme can be measured in a simple manner without complete purification of the enzyme being necessary.
The invention therefore relates to:
A method for enriching an anabolic p-hydroxyphenylpyruvate dioxygenase from plant cells, which comprises isolating the enzyme directly from a buffer in which the cells were homogenized.
The invention furthermore relates to an assay system for identifying inhibitors of p-hydroxyphenylpyruvate dioxygenase from plants, which comprises incubating an enriched HPPD from plants with a test substrate to be examined and determining the enzymatic activity of the enzyme in comparison with the activity of the uninhibited enzyme.
In particular, the invention relates to a method in which the plant tissue or cells are homogenized in extraction buffer, the extract is filtered, the supernatant is subjected to fractional ammonium sulfate precipitation, and the precipitate formed is redissolved.
Suitable extraction buffers are the extraction buffers conventionally used for plant cells, in particular the extraction buffer which is composed as follows:
20 mM phosphate buffer pH 7.0;
0.14M KCl;
0.1 mg/ml glutathione and
1% of insoluble polyvinylpyrrolidone.
Suitable test substrates are all compounds which are potential HPPD inhibitors. These potential inhibitors are preferably stucturally similar to the natural substrate of HPPD. However, other substances which do not bind in the active center of the enzyme, but which inhibit the enzyme in a different manner, can also be used.
The enzymatic activity can be determined by means of the methods known from the literature (see Bergmeyer, H. U., Methoden der enzymatischen Analyse Methods in enzymatic analysis!, Volumes 1 and 2, Verlag Chemie, Weinheim, (1974) and Suelter, C. H., Experimentelle Enzymologie: Grundlagen fur die Laborpraxis Experimental Enzymology: Fundamentals of Laboratory Practice!, Fischer Stuttgart (1990)).
A modified form of the method for measuring catabolic HPPDs from human liver has been described by Lindblad (Lindblad, B. (1971) Clin. Chim. Acta 34, 113-121). End-point measurements are used in this case for detecting 14 C--CO2, which is liberated from 14 C-p-hydroxyphenylpyruvate by the enzymatic activity of HPPD. If HPPD inhibitors are present in the reaction batch, the enzyme reaction and hence the liberation of CO2 are suppressed. This assay method allows inhibitors of the enzyme to be found.
It is preferred to carry out the assay in such a way that the enzymatic activity of the HPPD is started up after preincubation of the enriched HPPD with the potential inhibitor by adding the radiolabeled 14 C-p-hydroxyphenylpyruvate, stopping the reaction after a suitable incubation time, and measuring the enzymatic activity indirectly via the radioactivity which has been liberated.
It is self-evident that the assay according to the invention can also be carried out with the purified enzyme. The enzyme can be further enriched in a manner known per se by means of chromatography on anion exchangers, such as, for example, Q-Sepharose, by Pharmacia, followed by gel permeation chromatography, such as, for example, Superdex 200, by Pharmacia, but this is not necessary for carrying out the assay.
Surprisingly, a new class of HPPD inhibitors has now also been identified using this assay system. They are herbicides from the group of the 2-benzoylcyclohexane-1,3-diones. This is surprising since an entirely different mechanism of action is suggested in the literature for this compounds class on the basis of its herbicidal symptoms (they lead to bleaching of the plants). It is assumed that, analogously to other bleaching herbicides, they inhibit phytoene desaturase (Soeda, T. and Uchida, T. (1987) Pestic. Biochem. Physiol. 29, 35-42; Mayonada, D. J., Hatzios, K. K., Orcutt, D. M. and Wilson, H. P. (1989) Pestic. Biochem. Physiol. 35, 138-145). It was possible to demonstrate that this compounds class, while not inhibiting phytoene desaturase, does inhibit HPPD; under the assay conditions, 4.5�10-8 M 2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione (SC-0051, a typical representative of this class of herbicides) showed a 50% inhibition on the anabolic plant HPPD from maize (which corresponds to the IC50 value). Bleaching herbicides which have a different structure do not, in contrast, inhibit HPPD, but inhibit the enzyme phytoene desaturase.
However, the method according to the invention allows not only the activity of known herbicides to be demonstrated at the molecular level, but also novel, previously unknown herbicidal active substances which inhibit HPPD to be identified.
The invention therefore also relates to the novel herbicidal active substances found by the assay method according to the invention.
The invention therefore also relates to compounds of the formula (I) ##STR2## in which R1 is H, halogen, OH, alkoxy, CN, NO2 or haloalkyl,
R2 is H, halogen, OH, alkyl, alkoxy, haloalkyl, haloalkoxy or (alkoxy)-carbonyl,
R3 is H, halogen, OH, CN, NO2, haloalkyl, haloalkoxy or R4 S(O)m --, where R4 is alkyl and m is zero, one or two,
Q is a radical selected from the group of the formula ##STR3## where R5, R6, R7, R8 and R9 independently of one another are H, halogen, OH, CN, NO2, SO3 H, SO3 R4, SO2 NR14 R15, COOH, COOR4, CONR14 R15, O--COOR4, O--COR4, -alkyl, alkoxy, haloalkyl or haloalkoxy,
R10, R11 and R12 independently of one another are H, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy,
R13 is H, phenylsulfonyl, alkylsulfonyl or alkylcarbonyl, and
R14 and R15 independently of one another are H, alkyl, aryl or benzyl,
with the following provisos:
(i) R1 to R3 or R5 to R9 are not simultaneously hydrogen;
(ii) R5, R7 and R9 are not simultaneously hydroxy;
(iii) when R3 is alkoxy then R5 or R9 is halogen and when R7 is alkoxy then R6 or R8 is not hydrogen; and
(iv) when R1 is hydroxy then R5 and R9 are not hydroxy.
In the formula (I), the radicals alkyl, alkoxy, haloalkyl and haloalkoxy can in each case be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl or n-, i-, t- or 2-butyl. Aryl embraces aromatic and heteroaromatic radicals, such as, for example, phenyl, 2- or 3-naphthyl or 2-, 3- or 4-pyridyl. Halogen is fluorine, chlorine, bromine or iodine.
The use according to the invention of compounds of the formula (I) in which
R1 is H, halogen, OH, C1 -C3 -alkoxy, CN, NO2 or C1 -C3 -haloalkyl,
R2 is H, halogen, OH, C1 -C3 -alkyl, C1 -C3 -alkoxy, C1 -C2 -haloalkyl, C1 -C2 -haloalkoxy or (C1 -C2 -alkoxy)carbonyl,
R3 is H, halogen, OH, CN, NO2, C1 -C3 -haloalkyl, C1 -C2 -haloalkoxy or R4 S(O)m --, where R4 is C1 -C2 -alkyl and m is zero, one or two,
Q is a radical selected from the group of the formula ##STR4## where R5, R6, R7, R8 and R9 independently of one another are H, halogen, OH, CN, NO2, SO3 H, SO3 R4, SO2 NR14 R15, COOH, COOR4, CONR14 R15, O--COOR4, O--COR4, C1 -C4 -alkyl, C1 -C2 -alkoxy, C1 -C3 -haloalkyl or C1 -C2 -haloalkoxy,
R10, R11 and R12 independently of one another are H, halogen, C1 -C3 -alkyl, C1 -C2 -alkoxy, C1 -C3 -haloalkyl or C1 -C2 -haloalkoxy,
R13 is H, phenylsulfonyl, C1 -C2 -alkylsulfonyl or C1 -C2 -alkylcarbonyl, and
R14 and R15 independently of one another are H, C1 -C4 -alkyl, phenyl or benzyl,
is of particular interest.
Preferred is the use according to the invention of compounds of the formula (I) with at least one of the following characteristics:
R1 is preferably hydrogen, hydroxyl, fluorine, chlorine, bromine, cyano, nitro, methoxy, ethoxy, difluoromethyl, trifluoromethyl, chloromethyl, trichloromethyl, 2,2,2-trifluoroethyl or pentafluoroethyl,
R2 is preferably hydrogen, fluorine, chlorine, hydroxyl, propyl, ethyl, methyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,
R3 is preferably hydrogen, hydroxyl, fluorine, chlorine, bromine, cyano, nitro, difluoromethyl, trifluoromethyl, chloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, difluoromethoxy, trifluoromethoxy, methylsulfonyl or ethylsulfonyl;
Q is preferably the radical ##STR5## where R5, R6, R7, R8 and R9 preferably and independently of one another are hydrogen, fluorine, chlorine, bromine, cyano, nitro, hydroxyl, hydroxysulfonyl, ethoxysulfonyl, ethylaminosulfonyl, methylaminosulfonyl, carboxyl, ethoxycarbonyl, methoxycarbonyl, ethylaminocarbonyl, methylaminocarbonyl, ethoxycarbonyloxy, methoxycarbonyloxy, methylcarbonyloxy, t-butyl, i-propyl, propyl, ethyl, methyl, difluoromethyl, trifluoromethyl, chloromethyl, trichloromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy,
R10, R11 and R12 preferably and independently of one another are hydrogen, fluorine, chlorine, bromine, ethyl, methyl, difluoromethyl, trifluoromethyl, chloromethyl, trichloromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy,
R13 is preferably hydrogen, phenylsulfonyl, methylsulfonyl, ethylsulfonyl, methylcarbonyl or ethylcarbonyl, and
R14 and R15 preferably and independently of one another are hydrogen, butyl, propyl, ethyl, methyl or benzyl.
The uses according to the invention of compounds of the formula (I) with a combination of the abovementioned preferred characteristics are also preferred.
The compounds of the abovementioned formula (I) can be prepared, for example, by reacting aromatic carboxylic acid chlorides of the formula (II) ##STR6## in which the substituents R1, R2 and R3 are as defined under formula (I), with aromatic or heteroaromatic compounds of the type H-Q, in which Q is as defined under formula (I), in an inert solvent in the presence of a Lewis acid.
The compounds (I) are preferably prepared in aprotic solvents, in particular in halogenated hydrocarbons, such as, for example, dichloromethane, trichloromethane, 1,2-dichloromethane or 1,1,2,2-tetrachloroethane, at from -20� C. up to the boiling point of the reaction mixture, in particular at from room temperature to 50� C., the reaction being carried out in the presence of a catalytically to stoichiometrically employed amount of Lewis acid, such as, for example, aluminum chloride, titanium tetrachloride or boron trifluoride.
a) 3-(2,4-Dichlorobenzoyl)-1-phenylsulfonylpyrrole (Table 1, Example No. 150)
4.0 ml of 2,4-dichlorobenzoyl chloride and 4.00 g of aluminum chloride are stirred for 10 minutes at room temperature in 50 ml of 1,2-dichloroethane. A solution of 5.10 g of phenylsulfonylpyrrole in 20 ml of 1,2-dichloroethane is added dropwise to the mixture, and this is stirred for 2 hours at room temperature. The mixture is poured into ice-water and extracted using dichloromethane. The organic phase is dried and evaporated. Recrystallization of the residue from a mixture of ethyl acetate and petroleum ether gives 8.3 g (89% of theory) of 3-(2,4-dichlorobenzoyl)-1-phenylsulfonylpyrrole in the form of white crystals with a melting point of 122� C.
b) 2,5'-Dichloro-2'-hydroxy-3'-methyl-4-methylsulfonylbenzophenone (Table 1, Example No. 100)
5.06 g of 2-chloro-4-methylsulfonylbenzoyl chloride are added in portions at room temperature to a mixture of 2.85 g of 4-chloro-2-methylphenol and 5.40 g of aluminum chloride in 100 ml of 1,1,2,2-tetrachloroethane, and the mixture is subsequently refluxed for 7 hours. When cold, the reaction mixture is poured onto 200 g of ice and 500 ml of concentrated hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted twice using 50 ml of dichloromethane. The combined organic phases are washed until neutral, dried over magnesium sulfate and evaporated. Recrystallization from a mixture of ethyl acetate and diisopropyl ether gives 4.2 g (60% of theory) of 2,5'-dichloro-2'-hydroxy-3'-methyl-4-methylsulfonylbenzophenone in the form of colorless crystals with a melting point of 175�-180� C.
c) 2-(2,4-Dichlorobenzoyl)-1,4-quinone (Table 1, Example No. 91)
A solution of 2.49 g of 2-(2,4-dichlorobenzoyl)-1,4-dihydroxybenzene in 20 ml of glacial acetic acid is added dropwise at 10� C. in the course of 3 minutes to a solution of 1.60 g of sodium dichromate in 2 g of concentrated sulfuric acid and 60 ml of water. The reaction mixture is stirred vigorously for a further 30 minutes at 10�-15� C. and then filtered. The residue is washed with water until free from acid and recrystallized from diisopropyl ether. 1.74 g (70% of theory) of 2-(2,4-dichlorobenzoyl)-1,4-quinone are obtained in the form of yellowish-orange crystals with a melting point of 100� C.
d) 2,2',4'-Trichloro-6'-hydroxy-4-methylsulfonylbenzophenone (Table 1, Example No. 183)
3.00 g of 2-chloro-4-methylsulfonylbenzoyl chloride are added in portions at room temperature to a mixture of 1.97 g of 3,5-dichlorophenone and 3.23 g of aluminum chloride in 50 ml of 1,1,2,2-tetrachloroethane, and the mixture is subsequently refluxed for 7 hours. When cold, the reaction mixture is poured onto 100 g of ice and 20 ml of concentrated hydrochloric acid. The organic phase is removed, and the aqueous phase is extracted twice using 50 ml of dichloromethane. The combined organic phases are washed until neutral and subsequently extracted three times using in each case 25 ml of 2N sodium hydroxide solution. The combined alkaline extracts are brought to a pH of 2 using concentrated hydrochloric acid. The precipitate is filtered off, washed with water until neutral and dried. This gives 3.194 g (70% of theory) of 2,2',4'-trichloro-6'-hydroxy-4-methylsulfonylbenzophenone in the form of colorless crystals with a melting point of 123�-126� C.
The compounds listed in Table I are obtained analogously to the preparation examples described above.
TABLE I__________________________________________________________________________Compounds of the formula (I) according to the invention ##STR7##No. R1 R2 R3 Q M.p. �C.! IC50__________________________________________________________________________1 Cl H NO2 ##STR8## 135-139 <10-92 Cl CH3 SO2 CH3 ##STR9##3 Cl H OCF2 H ##STR10##4 Br H CN ##STR11##5 Br H NO2 ##STR12##6 Cl OC2 H5 SO2 CH3 ##STR13##7 Cl H SO2 CH3 ##STR14## 228 5.7 � 10-78 F OH CH2 CF3 ##STR15##9 NO2 F CH2 Cl ##STR16##10 Cl H SO2 CH3 ##STR17## 225 (decomp.) 1.8 � 10-711 OC2 H5 CF2 H SO2 CH3 ##STR18##12 OCH3 H Br ##STR19##13 OH Cl Cl ##STR20## 98-100 <10-914 Cl H SO2 CH3 ##STR21## 267 (decomp.)15 F COOCH3 CH2 CF3 ##STR22##16 Cl H Cl ##STR23## 14717 Cl Cl Br ##STR24##18 CN F CH2 Cl ##STR25##19 OH Cl Cl ##STR26## 95-10120 CH2 Cl OCH3 NO2 ##STR27##21 Br Cl Cl ##STR28##22 OH Cl Cl ##STR29## 126-12823 H H SO2 CH3 ##STR30## 22424 CH2 CF3 COOCH3 Cl ##STR31##25 F Cl SO2 CH3 ##STR32##26 OH Cl Cl ##STR33## 97-10027 NO2 H CF3 ##STR34##28 Br Cl OCF2 ##STR35##29 Cl H NO2 ##STR36## 19230 NO2 H Cl ##STR37##31 CCl3 F SO2 CH3 ##STR38##32 Cl H NO2 ##STR39## 17833 NO2 Cl Cl ##STR40##34 OH Cl Cl ##STR41## 124-12835 Cl H Cl ##STR42## 135 < � 10-936 Cl Cl CN ##STR43##37 Cl H SO2 CH3 ##STR44##38 Cl H SO2 CH3 ##STR45## 14739 Cl COOCH3 SO2 CH3 ##STR46##40 Cl H Cl ##STR47## 86 9.7 � 10-741 Cl C3 H7 SO2 CH3 ##STR48##42 OH Cl Cl ##STR49## 134-136 3.5 � 10-643 Cl H Cl ##STR50## 103 3.5 � 10-644 H OCF3 F ##STR51##45 NO2 H Cl ##STR52## 12546 Cl CH3 CF2 H ##STR53##47 Cl H SO2 CH3 ##STR54## 163-166 5.7 � 10-648 F COOCH3 OCF2 H ##STR55##49 Cl H Cl ##STR56## 9950 OH Cl Cl ##STR57## 98-10351 CH2 Cl C3 H7 SO2 CH3 ##STR58##52 NO2 OH Br ##STR59##53 CF3 H Cl ##STR60##54 Cl H Cl ##STR61##55 Cl Cl Cl ##STR62##56 OH Cl Cl ##STR63## 64-65 5.0 � 10-857 Br H OCF3 ##STR64##58 F CH3 F ##STR65##59 Br Cl Cl ##STR66##60 Cl H SO2 CH3 ##STR67## 16561 NO2 H OCF2 H ##STR68##62 CF3 Cl Cl ##STR69##63 Cl H SO2 CH3 ##STR70## 22764 CCl3 H Cl ##STR71##65 Cl H CF3 ##STR72##66 Cl H SO2 CH3 ##STR73## 22867 Cl CH3 OCF2 H ##STR74##68 Cl CF3 OCF2 H ##STR75##69 Cl H SO2 CH3 ##STR76##70 Cl H SO2 CH3 ##STR77## 240 (decomp.) 4.0 � 10-871 OCH3 COOCH3 SO2 CH3 ##STR78##72 Cl H SO2 C2 H5 ##STR79##73 CF3 CH3 Cl ##STR80##74 Cl H SO2 CH3 ##STR81## 151-15375 F OCF3 Cl ##STR82##76 Cl CF3 Cl ##STR83##77 H COOC2 H5 SO2 CH3 ##STR84##78 Cl H SO2 CH3 ##STR85##79 NO2 H Cl ##STR86## 160-16280 F Cl Cl ##STR87##81 OCH3 COOCH3 SO2 CH3 ##STR88##82 Cl Cl OH ##STR89## 137-13983 Cl Cl CF3 ##STR90##84 F C2 H5 Cl ##STR91##85 OCF2 H Cl Cl ##STR92##86 Cl H SO2 CH3 ##STR93## 15787 Cl H SO2 CH3 ##STR94## 108 2.4 � 10-788 Cl H SO2 CH3 ##STR95## 254-256 7.0 � 10-889 CF2 H Cl Cl ##STR96##90 Br H SO2 ##STR97##91 Cl H Cl ##STR98## 100 1.8 � 10-892 Cl C2 H5 CF3 ##STR99##93 F F F ##STR100##94 Cl Cl OH ##STR101## 149-15295 OH Cl Cl ##STR102## 118-12196 OC2 H5 Cl CF3 ##STR103##97 Cl H SO2 CH3 ##STR104## 180 (decomp.) 6.0 � 10-898 CN F F ##STR105##99 Cl H SO2 CH3 ##STR106##100 Cl H SO2 CH3 ##STR107## 175-180 6.2 � 10-9101 Cl H SO2 CH3 ##STR108## 183 <10-9102 Cl OCH3 NO2 ##STR109##103 F Cl Cl ##STR110##104 Cl H Cl ##STR111## 90105 Cl H SO2 C2 H5 ##STR112##106 Cl H SO2 CH3 ##STR113## 141-143107 H COOC2 H5 CN ##STR114##108 OCH3 H CF3 ##STR115##109 Cl H SO2 CH3 ##STR116## 171-175 <10-8110 H COOC2 H5 CF3 ##STR117##111 CCl3 Cl Cl ##STR118##112 CCl3 Cl Cl ##STR119##113 CF3 OCH3 Cl ##STR120##114 Cl H SO2 CH3 ##STR121## 234-235 9.0 � 10-9115 Cl H SO2 CH3 ##STR122## 98-100116 Cl Cl Br ##STR123##117 CN H Cl ##STR124##118 Cl CF3 Cl ##STR125##119 NO2 OC2 H5 Cl ##STR126##120 Cl H SO2 CH3 ##STR127## 182-187 <10-9121 F OCH3 F ##STR128##122 Cl Cl Cl ##STR129##123 CF3 COOCH3 Cl ##STR130##124 Cl H SO2 CH3 ##STR131## 188-192125 Cl COOC2 H5 Cl ##STR132##126 NO2 H Cl ##STR133##127 Cl H SO2 CH3 ##STR134## 136-140128 OH CF2 H Br ##STR135##129 F CH3 SO2 CH3 ##STR136##130 Cl H SO2 CH3 ##STR137## 198-202 1.0 � 10-9131 Cl H CF3 ##STR138##132 Cl H Cl ##STR139##133 H Cl Cl ##STR140##134 Cl H SO2 CH3 ##STR141## 278135 Cl OC2 H5 C2 F5 ##STR142##136 Cl H SO2 CH3 ##STR143## 105-108 3.0 � 10-7137 C2 F5 COOCH3 Cl ##STR144##138 Cl H Cl ##STR145## 173139 CN F Cl ##STR146##140 H Cl SO2 CH3 ##STR147##141 Cl H SO2 CH3 ##STR148## 182-185 1.1 � 10-9142 Cl CF2 H SO2 C2 H5 ##STR149##143 OC2 H5 COOCH3 SO2 CH3 ##STR150##144 CF3 Cl SO2 CH3 ##STR151##145 NO2 Cl OCF2 H ##STR152##146 Cl H Cl ##STR153## 178147 CH2 Cl Cl SO2 CH3 ##STR154##148 Cl H SO2 CH3 ##STR155## 193-195 9.2 � 10-7149 CF2 H H OCF3 ##STR156##150 Cl H Cl ##STR157## 122151 F CF3 F ##STR158##152 Cl H SO2 CH3 ##STR159## 143-144 1.2 � 10-7153 Cl Cl Cl ##STR160##154 Cl COOCH3 CF3 ##STR161##155 C2 F5 H NO2 ##STR162##156 Cl H SO2 CH3 ##STR163## 160-165 <10-9157 CF3 H F ##STR164##158 Cl CF3 H SO2 C2 H5 ##STR165##159 C2 F5 H Cl ##STR166##160 Cl H SO2 CH3 ##STR167## 142-145 2.3 � 10-7161 CCl3 H SO2 CH3 ##STR168##162 Cl CF3 Cl ##STR169##163 Cl H SO2 CH3 ##STR170## 167-170 1.2 � 10-8164 Br OCF2 H CF3 ##STR171##165 Cl OCH3 SO2 CH3 ##STR172##166 Cl H SO2 CH3 ##STR173## 154-155 2.0 � 10-8167 H F CCl3 ##STR174##168 Cl H SO2 CH3 ##STR175## 161169 CH2 CF3 Cl Cl ##STR176##170 CF3 H OCH3 CN ##STR177##171 Cl H SO2 CH3 ##STR178## 228-230 2.2 � 10-8172 CF3 H Cl ##STR179##173 Cl H Cl ##STR180## 92174 Br OCF3 CH2 Cl ##STR181##175 Cl H SO2 CH3 ##STR182## 195-196 1.2 � 10-8176 OH COOC2 H5 CF2 H ##STR183##177 H OCH3 F ##STR184##178 Cl H SO2 CH3 ##STR185## 118-120 4.0 � 10-9179 Br OCH3 CF3 ##STR186##180 NO2 COOCH3 OCF2 H ##STR187##181 Cl H Cl ##STR188## 134182 CN F CH2 CF3 ##STR189##183 Cl H SO2 CH3 ##STR190## 123-125 4.8 � 10-9184 Br OCH3 CF2 H ##STR191##185 Cl OCF2 H NO2 ##STR192##186 OC2 H5 COOC2 H5 Cl ##STR193##187 Cl H SO2 CH3 ##STR194## 117-121 4.0 � 10-7188 F Cl CCl3 ##STR195##189 Cl H Cl ##STR196## 101190 Cl OCF3 SO2 CH3 ##STR197##191 Cl H SO2 CH3 ##STR198## 164-166 <10-8192 Br OH CF3 ##STR199##193 OH Cl Cl ##STR200## 116-118194 Cl Cl OH ##STR201## 69-71195 Br H CCl3 ##STR202##196 Cl H SO2 CH3 ##STR203## 162-168 <10-9197 F H Br ##STR204##198 Cl H Cl ##STR205## 132199 Cl Br CF3 ##STR206##200 Cl H Cl ##STR207## 135201 Cl H SO2 CH3 ##STR208## 115-118 <10-9202 F COOCH3 SO2 CH3 ##STR209##203 CH2 CF3 H Br ##STR210##204 Cl H SO2 CH3 ##STR211## 118-121 <10-5__________________________________________________________________________
The invention furthermore relates to the use of the herbicidal active substances identified by means of the assay method according to the invention in plant populations.
Suitable plant populations are, in particular, crop plants.
In the examples which follow, the invention is described further and illustrated in greater detail with the aid of examples. Percentages are by weight unless otherwise specified.
To enrich the anabolic HPPD from plant tissues, young etiolated maize plants were homogenized in extraction buffer (20 mM phosphate buffer pH 7.0; 0.14M KCl; 0.1 mg/ml glutathione and 1% insoluble polyvinylpyrrolidone) for 3�10 seconds, for example in a Waring blender. The extract was filtered (all other isolation steps were carried out at 4� C.) and centrifuged (20 minutes; 10,000 g). The supernatant was subjected to fractional ammonium sulfate precipitation. At from 20 to 40% saturation of the solution with ammonium sulfate, HPPD precipitated. At this stage, it was possible to store the enzyme at -80� C. following dialysis in a suitable buffer, such as, for example, 20 mM phosphate buffer pH 7.0; 0.14M KCl; 0.1 mg/ml glutathione. This degree of purity of the enzyme is sufficient for identifying inhibitors.
The enzyme assays were performed in 20 ml polyethylene screw-top containers. Two hypodermic needles (0.9�40 mm) were pushed through the screw-top cap. One of the hypodermic needles was bent to form a hook onto which a small filter paper disk of diameter 10 mm was placed. The filter paper was moistened with 25 μl of methylbenzethonium hydroxide (Sigma). The second hypodermic needle was used for injecting start and stop solution into the screw-top container.
The enzyme reaction mix contained:
1 ml of 0.1M phosphate buffer, pH 7.3;
2 g/l of bovine liver catalase;
100 μl of a mixture of 3 mM dichlorophenolindophenol and
150 mM glutathione (reduced);
25 μl of acetone (or potential inhibitors dissolved in acetone) and
enzyme in a total volume of 1,635 μl.
After preincubation for 5 minutes at 30� C., the reaction was started by injecting 800 μl of 14 C-p-hydroxyphenylpyruvate. The reaction was stopped by injecting 600 μl of 1N H2 SO4, incubation was continued for 15 minutes, and the radioactivity which was liberated was determined on the small filter paper disks in a liquid scintillation counter.
Thin-layer chromatography analysis of the incorporation of radioactivity from 14 C-tyrosine into plastoguinone. Wheat plants were either not treated (A), or sprayed with a standard screening formulation (B) or with 100 g/ha of SC-0051 in this screening formulation (C), and then incubated with 14 C-tyrosine. The lipophilic metabolites of the wheat were extracted using chloroform, separated on silica gel 60 HPTLC plates using chloroform: diethyl ether (99:1), and the radioactivity was analyzed by thin-layer scanner. The incorporation of radioactivity from tyrosine into plastoquinone (see FIG. 1, band 2) can be seen clearly in the control batches (A) and (B), while plastoquinone biosynthesis is inhibited by the use of SC-0051 (C).
The test was carried out analogously to Example 3, but a different inhibitor which also results in bleaching symptoms was used (clomazone). While SC-5001 shows a marked inhibition of HPPD (o), the other bleaching herbicide has no inhibitory action on HPPD () (see FIG. 2).
HPPD catalyzes the transformation of p-hydroxyphenylpyruvate to homogentisic acid. If HPPD inhibition is responsible for the herbicidal activity of an inhibitor, then it should be possible to neutralize the herbicidal effect by supplementation with homogentisic acid. This was demonstrated by an experiment with the dockweed Lemna gibba. The plant was grown in a sterile aqueous medium supplemented as described in Table 1.
Table II: Neutralization of the effect of SC-0051 by homogentisic acid
______________________________________Supplementation Number of L. gibba plantsof the medium Control 10-7 M SC-0051______________________________________-- 25 31 mM HPPD 22 21 mM HGA 29 32______________________________________
Batches of three Lemna plants in 100 ml of sterile medium were incubated for six days with sterile-filtered supplements. SC-0051 was added in the form of a 10-3 M stock solution (active substance in acetone). The number of newly formed plants was determined on day six.
______________________________________ Growth inhibition ofExample No. Lemna (%)from Table I IC50 value (M) 10-4 M 10-5 M 10-6 M______________________________________183 4.8 � 10-9 98 82 81160 2.3 � 10-7 80 72 12204 >10-5 28 12 --171 2.2 � 10-8 98 93 93100 6.2 � 10-9 98 96 92______________________________________
Table 2 shows IC50 values of p-hydroxyphenylpyruvate dioxygenase inhibition by a range of benzophenone derivatives in comparison with growth inhibition of Lemna gibba.
The IC50 value is the molar concentration of the inhibitor at which 50% of the enzyme activity are inhibited. The growth of Lemna was measured as described in: Schulz, A., Ort, O., Beyer, P. and Kleinig, H.; SC-0051, a 2-benzoylcyclohexane-1,3-dione bleaching herbicide, is a potent inhibitor of the enzyme p-hydroxyphenylpyruvate dioxygenase. FEBS-Letters, 1993, 318 (2), 162-166.
It can be seen from this table that the herbicidal activity of the benzophenone derivatives is correlated with the in vitro activity.
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New Times News
News on New Times (Ticker: NYT) continually updated from thousands of sources around the net.
37 Stars You'll Be Shocked Used To Be Couples
This Ferret REALLY Thinks It Can Make This Big Jump. Does It Succeed?
Here Are 16 Cats Sleeping in IKEA Doll Beds. YEP. IT'S THE CUTEST.
The 27 Most Dramatic Red Carpet Style Transformations You'll Ever See
35 Celebrities Who Were Homeless At Some Point In Their Lives
Top 10 YouTube Comedy Channels -TopX Ep. 3
Which 'Brady Bunch' Character Are You?
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Phoronix News Archives
Phoronix Global To Shutdown At Year's End
Having been succeeded by OpenBenchmarking.org, Phoronix Global is facing closure at the end of the 2013 calendar year.
6 July 2013 - PTS Global
Soliciting Feedback On The New Phoronix Design
As mentioned last month on Phoronix, a major revision to Phoronix.com is in-development. Prior to the launch later this month, your feedback on the latest concepts are appreciated.
5 July 2013 - PHXCMS8 - 55 Comments
June Was A Very Diverse Month For Linux Enthusiasts
With the end of a month comes our usual monthly recap. A lot of interesting Linux changes happened in June from dynamic power management in the Radeon DRM driver to Mir and Wayland news.
30 June 2013 - 173 News Posts, 20 Articles
The New Phoronix Site Is Launching Soon
The overhauled Phoronix site is on track for making its debut in July.
23 June 2013 - PHXCMS8 - 30 Comments
The First Release Of Phoronix Test Suite "Sokndal"
Phoronix Test Suite 4.8 "Sokndal" is under heavy development following the stable Phoronix Test Suite 4.6.1 update that arrived earlier this month. So far there's min/max reporting improvements, continued work on bettering Apple OS X benchmarks, and a lot more to come.
20 June 2013 - Phoronix Test Suite 4.8 - 10 Comments
Min / Max FPS Comes To Test Results
With Phoronix Test Suite 4.8 "Sokndal", the minimum and maximum performance results are now being commonly displayed along side the rest of the results.
16 June 2013 - Phoronix Test Suite - 15 Comments
The Phoronix Migration Is Fully Complete
After some rough hours, all of the Phoronix infrastructure should be located now within its new data center. If any problems are experienced in getting your dose of Phoronix, please contact us.
16 June 2013 - Phoronix Server - 3 Comments
Phoronix Server Migration Complete
Tonight (15 June 21:00 CST) we are upgrading our server infrastructure and moving the Phoronix web properties to a new data center.
15 June 2013 - Phoronix Server Migration - 6 Comments
Phoronix Test Suite 4.6.1 Drives OS X Benchmarking
The first point release to Phoronix Test Suite "Utsira" has been released with some marked improvements for Apple OS X and other minor enhancements.
7 June 2013 - 4.6.1-Utsira - 7 Comments
Previewing The New Phoronix Design
A new site design and layout is coming soon to Phoronix.
6 June 2013 - Phoronix.com - 46 Comments
Phoronix.com Turns Nine Years Old, PTS Turns Five
It was nine years ago today, on 5 June 2004, that I founded Phoronix.com as a long expedition to ultimately enrich the Linux hardware experience and to become the leading source for providing Linux hardware reviews. Additionally, it's five years ago today that marks the public release of Phoronix Test Suite 1.0.
5 June 2013 - Phoronix - 17 Comments
Gaming, Linux Desktop Advances For May 2013
With the end of May comes our usual end of the month summary about the most popular Linux news stories this month that appeared on Phoronix and other announcements.
31 May 2013 - End Of Month - 11 Comments
Phoronix Test Suite 4.6.0 "Utsira" Released
Phoronix Test Suite 4.6.0 (codenamed "Utsira") has been officially released today with compiler improvements, support for the HHVM virtual machine, BSD support improvements, and other hardware/software improvements.
21 May 2013 - Version 4.6.0 - 1 Comment
Phoronix Test Suite 4.6 "Utsira" Milestone 2 Released
The second development release of the upcoming Phoronix Test Suite 4.6-Utsira open-source benchmarking platform is now available for Linux, BSD, Solaris, OS X, and Windows operating systems.
16 May 2013 - 4.6-Utsira
A New Set Of OpenGL Benchmarks Come To OpenBenchmarking
FurMark, TessMark, and other advanced OpenGL 2.1/3.2/4.0 benchmarks are now available via the Phoronix Test Suite and OpenBenchmarking.org.
11 May 2013 - OpenGL Tests - 10 Comments
LLVM 3.3 Planned As A Phoronix Birthday Present
The LLVM 3.3 release of the compiler infrastructure and adjoining Clang C/C++ compiler is planned for release on the day that Phoronix turns nine years old.
3 May 2013 - LLVM 3.3 - 6 Comments
What Was Striking On Phoronix Last Month
In April on Phoronix there were 221 published original news articles and 20 featured length articles. Here's what was most popular among the plethora of original Linux content with a bent on performance testing, graphics drivers, power management, and Linux gaming.
1 May 2013 - April 2013
More Details On The HHVM Virtual Machine Design
After earlier this week delivering benchmarks showing Facebook's HipHop 2.0 Virtual Machine is very fast, a Facebook engineer commented in our forums about some of the design choices that were made.
12 April 2013 - HipHop - 1 Comment
Phoronix Test Suite 4.6-Utsira Milestone 1 Released
The first development release of Phoronix Test Suite 4.6 (codenamed "Utsira") is now available for open-source, cross-platform, automated benchmarking and testing.
11 April 2013 - First Development - 1 Comment
PTS 4.4.1 Arrives, Benchmark Windows 8 vs. Ubuntu
Succeeding last month's release of Phoronix Test Suite 4.4, the first point release to "Forsand" has been made available. There's minor improvements and fixes throughout along with some notable work on the Microsoft Windows side.
14 March 2013 - Phoronix Test Suite 4.4.1 - 4 Comments
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text:
Dragon Age: Inquisition by all accounts is an incredibly large game. Claims of over one hundred hours of gameplay by the publisher are apparently, not exaggeration. And that's just for the single player. Dragon Age: Inquisition also sports a four player online co-op mode where players team up and dive into pseudo-random dungeons for loot and glory. We'll have a full review of Dragon Age: Inquisition in the coming week or so, but for now, we wanted to give you our impressions of just the cooperative gameplay.
New Dying Light Video is a Trap
Set to classical music.
Another day, another horde of undead trying to gnaw your face off. Techland's upcoming zombie shooter Dying Light hasn't pulled its punches when it comes to living-on-dead gore. Previous videos have shown off baseball bat weapons, drop kicks, exploding face guts and more. But now? Now we've g...Comments More Dying Light News
Playstation Co-Op Games Sale Now Live
What do we want? Co-op games! When do we want it? After our faces are stuffed with turkey!
Christmas has come early for us co-op gamers (at least for those of us on Sony platforms)! Playstation just announced a slick new deal focused entirely on co-op gaming, presumably to help calm your family's nerves after two hours of bickering about why your aunt brought her new boyfri...
New Dev Diary For Resident Evil: Revelations 2 Details Claire's Updated Look
Now featuring emotional scarring!
Claire Redfield, the star of Resident Evil: Revelations 2, has had a rough life. For one, she's spent most of it chasing after her deadbeat brother, who's too busy following his dream of murdering every zombie on God's green earth to take a minute and send her a text. In doin...
Lost Ark ARPG is a Game You Want Right Now
Is "hnnngh" descriptive enough?
Don't you just love these "secret" games that seem to exist only to make you go WOW? Lost Ark is an action RPG in the vein of Diablo or Torchlight currently in the works by a Korean team Smilegate. To sum it up neatly, it's basically just like Torchlight, only with the special atta...Comments More Lost Ark News
Far Cry 4 Co-Op FAQ
Keys to honey badgers.
Welcome to Kyrat, the setting for Far Cry 4. Set in the Himalayan mountains, players will experience a wide variety landscapes to see and activities to complete. But what can they experience with a friend? Here's our FAQ....Comments Watch Video More Far Cry 4 News
Ultimate Vault Hunter Mode in the Works for Borderlands: The Pre-Sequel
Plus some other, secreter freebies.
Secret Borderlands: The Pre-Sequel news alert! With the release of the Handsome Jack Doppelganger Pack DLC, a tiny little future update was mentioned off-hand by Gearbox Software. Alongside the official DLC releases, some free updates are also in the works, including Ultimate Vault Hunter mode...


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Fallout: New Vegas will be a slow burner says Bethesda
Bethesda has confidence that Fallout: New Vegas will see continued success in the same way as Fallout 3 has.
The Elder Scrolls developer believes that with a steady stream of DLC similar to that of Fallout 3, New Vegas will continue to see strong sales.
Marketing and PR manager for Europe, Sarah Seaby said: "We believe that through a combination of DLC, our strong marketing and PR and by managing our lifecycle properly, that well see a long burn of sales in a similar way to Fallout 3."
Fallout: New Vegas made it to number one in the sales charts in its debut week outselling its predecessor.
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- Report finds that the 100 USD tier of Assassin's Creed: Unity's microtransactions is completely unnecessary
- Final Fantasy Type-0 HD gets a new trailer
- Bungie deconstructs their latest Destiny patch, hints at what is coming next
- DayZ creator Dean Hall could join UK studio Improbable
- Shadow Of Mordor arrives on last-gen consoles
- David Braben apologises for ditching Elite: Dangerous's offline mode, outlines refund criteria
- Microsoft celebrates the 1st birthday of the Xbox One with free access to Sunset Overdrive
- Hacker group leaks account details for thousands of PSN, Origin, Windows Live and 2K Game Studios accounts
- RedLynx promises online multiplayer is coming to Trials Fusion early next year


text:
In 2011, The DJBooth introduced readers to Coolroy's Charlie, a introductory project from the once buzzing West Coast native.
Unfortunately, in the 30 months following the free release, Coolroy only appeared on our pages a total of two times. Part of the story is that the emcee became a father for the first time. The other, less glamorous part includes an addiction to molly, getting evicted from his home, becoming homeless, committing a series of crimes and contemplating suicide.
With the help of family, friends and peers in the music game, Coolroy changed the ending to his story. Hellbent on "finishing something for the first time in my life," the Los Angeles bred artist born Dominik C. Franklin has released nine. The project, which took two full years to create, features previously-released selection "I'm Fine." Guest appearances include Krayzie Bone and Jhené Aiko, while the album is produced in-full by David Manzoor.
Fans can also check out Coolroy's previous albums: Coolroy - Charlie
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Discover the best new songs, videos, and albums added to the Booth.


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Being resourceful on crutches #selfie
25 Reasons Why Crutches Are The Spawn Of The Devil
Even though they hold you up, you still can't stand them.
1. You can't ever hold ANYTHING…
2. …So you must invent new ways to carry things.
3. Your armpits become bruised to their very cores.
4. Stairs become your biggest hurdle.
5. You must think of creative ways to keep up to the same pace as your friends.
6. People can hear you coming from a mile away because they're so loud.
7. Anything with wheels become your best friend.
8. ANYTHING but the crutches.
9. Because you're sick of moving, you spend a ton of time sitting, dwelling alone in your thoughts.
10. It sucks getting in and out of the car with them.
11. People always want to take your crutches, because "they look fun."
12. You can't have a normal night out.
13. Exercise has become a thing of the past.
14. If your crutches fall on the floor, you have to complete an awkward balancing act to pick them up.
15. Walking through inclement weather? It's all over.
16. Your arms and back are severely sore from all the upper body work.
17. Even giving them googly eyes won't make them better.
18. You pray for someone to open the door for you, because it's nearly impossible.
19. Blisters on blisters.
20. You've debated bearing the pain and just walking.
21. You'd rather hold it than get up to go to the bathroom.
22. You have a permanent smell of sweaty rubber on your hands from the grips.
23. No matter what, they will ALWAYS make you fall at least once.
24. Only fellow crutch-goers can truly feel your pain.
25. You count down the days until you can say goodbye to these bastards.
Dear crutches, thanks for doing us the solid of helping us walk, but the tribe has spoken…it's time for you to die a slow death. Best wishes. <3 Humanity
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Native advertising is having its big moment. When done right, it has tremendous pull with consumers. According to Nielsen, native ads produce as much as an 82% in brand lift. An infographic from MDG Advertising says 70% of individuals reported that they would prefer "to learn about products through content rather than through traditional advertising."
May 19, 2011
RingCube Technologies, a provider of personalization solutions for virtual desktops, announced the general availability of vDesk v 4.0. vDesk v.4.0 is a new enterprise desktop virtualization solution that expands an organization's virtual desktop user base and enables faster and more efficient VDI rollouts.
With RingCube, employees who require highly personalized desktops can now be included in VDI implementations. RingCube's vDesk is a complementary offering to VMware View and Citrix XenDesktop that offers personalized user desktops without adding any additional management overhead.
RingCube can help maximize the virtual desktop userbase by expanding rollouts to more employees, and improves general virtual desktop usage by minimizing setup requirements and the need for specialized IT skills.


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Large Financial Services Firm Gains Cost Efficiencies with Ric...Document at a Glance Abstract This IDC Buyer Case Study looks at how a large financial services organization selected Ricoh as its managed print and document services (MPDS) partner. Organizations that are currently engaged in or are ... IDC, 1 day ago
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said its chief financial officer will retire, and it unveiled a cost-savings plan that includes eliminating a management layer at its Olive Garden and LongHorn Steakhouse chains. The company, which also said it intends to close its aviation ...Austin American Statesman, 5 days ago Will Cost Cuts Boost Darden In Hot Restaurants Group? Investor's Business Daily, 4 days ago Darden announces job and cost cuts as well as management changes as part of reshaping effort INO.com, 5 days ago
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Bottom line on climate change: It's costing you money
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- 1 Man charged with putting camera in ex's shower says he was filming chickens
- 2 Study seeks to analyze hunter-bear interactions
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- 4 Bleskin injury further tangles Bobcats' QB situation
- 5 Father: 'Nothing could prepare you to lose part of your soul'
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BOZEMAN — Heifers being prepared for breeding don't have to eat like pigs, stuffing themselves at all-you-can-eat feed bunks with unlimited refills, according to scientists at a Montana State University experiment station.
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Guitar Hero: On Tour - Trailer
Ok, so these kids are pretty annoying, but Guitar Hero On Tour looks very exciting indeed. Especially if you harbour secret rock star fantasies like us.
Comments (17)
Dragon Age Inquisition walkthrough Our guide to the massive third game.
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Quality of life in adult survivors of critical illness: A systematic review of the literature
- David W. Dowdy,
- Mark P. Eid,
- Artyom Sedrakyan,
- Pedro A. Mendez-Tellez,
- Peter J. Pronovost,
- Margaret S. Herridge,
- Dale M. Needham
- … show all 7 hide
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Objective: To determine how the quality of life (QOL) of intensive care unit (ICU) survivors compares with the general population, changes over time, and is predicted by baseline characteristics. Design: Systematic literature review including MEDLINE, EMBASE, CINAHL and Cochrane Library. Eligible studies measured QOL ≥30 days after ICU discharge using the Medical Outcomes Study 36-item Short Form (SF-36), EuroQol-5D, Sickness Impact Profile, or Nottingham Health Profile in representative populations of adult ICU survivors. Disease-specific studies were excluded. Measurements and results: Of 8,894 citations identified, 21 independent studies with 7,320 patients were reviewed. Three of three studies found that ICU survivors had significantly lower QOL prior to admission than did a matched general population. During post-discharge follow-up, ICU survivors had significantly lower QOL scores than the general population in each SF-36 domain (except bodily pain) in at least four of seven studies. Over 1–12 months of follow-up, at least two of four studies found clinically meaningful improvement in each SF-36 domain except mental health and general health perceptions. A majority of studies found that age and severity of illness predicted physical functioning. Conclusions: Compared with the general population, ICU survivors report lower QOL prior to ICU admission. After hospital discharge, QOL in ICU survivors improves but remains lower than general population levels. Age and severity of illness are predictors of physical functioning. This systematic review provides a general understanding of QOL following critical illness and can serve as a standard of comparison for QOL studies in specific ICU subpopulations
- Angus DC, Carlet J (2003) Surviving intensive care: a report from the 2002 Brussels Roundtable. Intensive Care Med 29:368–377
- Rubenfeld GD, Angus DC, Pinsky MR, Curtis JR, Connors AFJ, Bernard GR (1999) Outcomes research in critical care: results of the American Thoracic Society Critical Care Assembly Workshop on Outcomes Research. Am J Respir Crit Care Med 160:358–367
- Hayes JA, Black NA, Jenkinson C, Young D, Rowan KM, Daly K, Ridley S (2000) Outcome measures for adult critical care: a systematic review. Health Technol Assess 4:24
- Chaboyer W, Elliott D (2000) Health-related quality of life of ICU survivors: review of the literature. Intensive Crit Care Nurs 16:88–97 CrossRef
- Buckley TA, Cheng AY, Gomersall CD (2001) Quality of life in long-term survivors of intensive care. Ann Acad Med Singapore 30:287–292
- Niskanen M (1998) Quality of life after intensive care. Schweiz Med Wochenschr 128:1474–1477
- Black NA, Jenkinson C, Hayes JA, Young D, Vella K, Rowan KM, Daly K, Ridley S (2001) Review of outcome measures used in adult critical care. Crit Care Med 29:2119–2124 CrossRef
- 8: Heyland DK, Guyatt G, Cook DJ, Meade M, Juniper E, Cronin L, Gafni A (1998) Frequency and methodologic rigor of quality-of-life assessments in the critical care literature. Crit Care Med 26:591–598
- Rubenfeld G (2002) Looking beyond 28-day all-cause mortality. Crit Care 6:293–294
- Parîzková R, Cerný V, Dostá P, Vasátko L, Hora P, Herold I, Novák I, Nalos D (2001) Monitoring quality of life in critically ill patients: A multicenter study. Anesteziol Neodkladna Pece 12:240–251
- Ware JE, Snow KK, Kosinski M, Gandek B (1993) SF-36 health survey: Manual and interpretation guide. The Health Institute, Boston
- The EuroQol Group (1990) EuroQol—a new facility for the measurement of health-related quality of life. Health Policy 16:199–208 CrossRef
- Bergner M, Bobbitt RA, Carter WB, Gilson BS (1981) The Sickness Impact Profile: development and final revision of a health status measure. Med Care 19:787–805
- Hunt SM, McKenna SP, McEwen J, Williams J, Rapp E (1981) The Nottingham Health Profile: subjective health status and medical consultations. Soc Sci Med 15A:221–229
- Patrick DL, Danis M, Southerland LI, Hong G (1988) Quality of life following intensive care. J Gen Intern Med 3:218–223
- Fernandez RR, Cruz JJ, Vazquez Mata G (1996) Validation of a quality of life questionnaire for critically ill patients. Intensive Care Med 22:1034–1042
- Tian ZM, Miranda DR (1995) Quality of life after intensive care with the sickness impact profile. Intensive Care Med 21:422–428
- Chrispin PS, Scotton H, Rogers J, Lloyd D, Ridley SA (1997) Short Form 36 in the intensive care unit: assessment of acceptability, reliability and validity of the questionnaire. Anaesthesia 52:15–23
- Hurel D, Loirat P, Saulnier F, Nicolas R, Brivet F (1997) Quality of life 6 months after intensive care: results of a prospective multicenter study using a generic health status scale and a satisfaction scale. Intensive Care Med 23:331–337
- Dixon JJ (1997) Patient and relative satisfaction with intensive care, importance of duration and quality of life. Clin Intensive Care 8:63–68
- Berlin JA (1996) Randomized trial comparing masked/unmasked meta-analyses. In: Report AHCPR-97–20. Agency for Health Care Policy and Research, Rockville, MD, USA
- Harris RP, Helfand M, Woolf SH, Lohr KN, Mulrow CD, Teutsch SM, Atkins D for the Methods Work Group, Third US Preventive Services Task Force (2001) Current methods of the US Preventive Services Task Force: a review of the process. Am J Prev Med 20 [Suppl 3]:21–35
- Pettila V, Kaarlola A, Makelainen A (2000) Health-related quality of life of multiple organ dysfunction patients one year after intensive care. Intensive Care Med 26:1473–1479
- Kaarlola A, Pettila V, Kekki P (2003) Quality of life six years after intensive care. Intensive Care Med 29:1294–1299 CrossRef
- Kleinpell RM (2003) Exploring outcomes after critical illness in the elderly. Outcomes Manag 7:159–169
- Wehler M, Geise A, Hadzionerovic D, Aljukic E, Reulbach U, Hahn EG, Strauss R (2003) Health-related quality-of-life of patients with multiple organ dysfunction: individual changes and comparison with normative population. Crit Care Med 31:1094–1101
- Graf J, Koch M, Dujardin R, Kersten A, Janssens U (2003) Health-related quality of life before, 1 month after, and 9 months after intensive care in medical cardiovascular and pulmonary patients. Crit Care Med 31:2163–2169 CrossRef
- Eddleston JM, White P, Guthrie E (2000) Survival, morbidity, and quality of life after discharge from intensive care. Crit Care Med 28:2293–2299 CrossRef
- Kvale R, Flaatten H (2003) Changes in health-related quality of life from 6 months to 2 years after discharge from intensive care. Health Qual Life Outcomes 1:2
- Kvale R, Ulvik A, Flaaten H (2003) Follow-up after intensive care: a single center study. Intensive Care Med 29:2149–2156 CrossRef
- Vedio AB, Chinn S, Warburton FG, Griffiths MP, Leach RM, Treacher DF (2000) Assessment of survival and quality of life after discharge from a teaching hospital general intensive care unit. Clin Intensive Care 11:39–46
- Ridley SA, Chrispin PS, Scotton H, Rogers J, Lloyd D (1997) Changes in quality of life after intensive care: comparison with normal data. Anaesthesia 52:195–202
- Flaatten H, Kvale R (2001) Survival and quality of life 12 years after ICU. A comparison with the general Norwegian population. Intensive Care Med 27:1005–1011
- Kvale R, Flaaten H (2002) Changes in intensive care from 1987 to 1997—has outcome improved? A single centre study. Intensive Care Med 28:1110–1116
- Chaboyer W, Foster M, Creamer J (2002) Health status of ICU survivors: a pilot study. Aust Crit Care 15:21–26
- Badia X, Diaz-Prieto A, Gorriz MT, Herdman M, Torrado H, Farrero E, Cavanilles JM (2001) Using the EuroQol-5D to measure changes in quality of life 12 months after discharge from an intensive care unit. Intensive Care Med 27:1901–1907 CrossRef
- Granja C, Teixeira-Pinto A, Costa-Pereira A (2002) Quality of life after intensive care—evaluation with the EQ-5D questionnaire. Intensive Care Med 28:898–907 CrossRef
- Granja C, Dias C, Costa-Pereira A, Sarmento A (2004) Quality of life of survivors from severe sepsis and septic shock may be similar to that of others who survive critical illness. Crit Care 8:R91–98
- Garcia Lizana F, Peres Bota D, De Cubber M, Vincent JL (2003) Long-term outcome in ICU patients: what about quality of life? Intensive Care Med 29:1286–1293
- Sznajder M, Aegerter P, Launois R, Merliere Y, Guidet B, CubRea (2001) A cost-effectiveness analysis of stays in intensive care units. Intensive Care Med 27:146–153 CrossRef
- Miranda DR (1994) Quality of life after cardiopulmonary resuscitation. Chest 106:524–530
- Short TG, Buckley TA, Rowbottom MY, Wong E, Oh TE (1999) Long-term outcome and functional health status following intensive care in Hong Kong. Crit Care Med 27:51–57
- Kleinpell RM (1991) Quality of life of critically ill elderly patients. PhD thesis, University of Illinois at Chicago
- Sage WM, Rosenthal MH, Silverman JF (1986) Is intensive care worth it? An assessment of input and outcome for the critically ill. Crit Care Med 14:777–782
- Frick S, Uehlinger DE, Zurcher Zenklusen RM (2002) Assessment of former ICU patients' quality of life: comparison of different quality-of-life measures. Intensive Care Med 28:1405–1410
- Bell D, Turpin K (1994) Quality of life at three months following admission to intensive and coronary care units. Clin Intensive Care 5:276–281
- Niskanen M, Ruokonen E, Takala J, Rissanen P, Kari A (1999) Quality of life after prolonged intensive care. Crit Care Med 27:1132–1139
- Crosby RD, Kolotkin RL, Williams GR (2003) Defining clinically meaningful change in health-related quality of life. J Clin Epidemiol 56:395–407
- Hofhuis J, Hautvast JL, Schrijvers AJ, Bakker J (2003) Quality of life on admission to the intensive care: can we query the relatives? Intensive Care Med 29:974–979
- Rogers J, Ridley S, Chrispin P, Scotton H, Lloyd D (1997) Reliability of the next of kins' estimates of critically ill patients' quality of life. Anaesthesia 52:1137–1143
- Title
- Quality of life in adult survivors of critical illness: A systematic review of the literature
- Journal
Intensive Care Medicine
Volume 31, Issue 5 , pp 611-620
- Cover Date
- 2005-05-01
- 10.1007/s00134-005-2592-6
- Print ISSN
- 0342-4642
- Online ISSN
- 1432-1238
- Publisher
- Springer-Verlag
- Additional Links
- Keywords
- Critical care
- Critical illness
- Health status indicators
- Intensive care units
- Outcome assessment (health care)
- Quality of life
- Industry Sectors
- Authors
- David W. Dowdy (1) (3)
- Mark P. Eid (3)
- Artyom Sedrakyan (2)
- Pedro A. Mendez-Tellez (4)
- Peter J. Pronovost (2) (4) (5)
- Margaret S. Herridge (7)
- Dale M. Needham (6)
- Author Affiliations
- 1. Department of Epidemiology, Johns Hopkins Bloomberg School of Public Health, Baltimore, MD, USA
- 3. School of Medicine, Johns Hopkins University, Baltimore, MD, USA
- 2. Department of Health Policy and Management, Johns Hopkins Bloomberg School of Public Health, Baltimore, MD, USA
- 4. Department of Anesthesiology & Critical Care Medicine, Johns Hopkins University, Baltimore, MD, USA
- 5. Department of Surgery, Johns Hopkins University, Baltimore, MD, USA
- 7. Interdepartmental Division of Critical Care Medicine, University of Toronto, Toronto, Ontario, Canada
- 6. Division of Pulmonary & Critical Care Medicine, Johns Hopkins University, 1830 E. Monument Street, 5th floor, Baltimore, MD, 21205, USA


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Explosive small arms projectile
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An explosive small arms projectile is disclosed. Prior art projectiles of this kind include a lead core for increased mass which core is formed with a blind hole for receiving an explosive and the necessary detonating device.The projectile of the invention comprises a jacket (102) of a metal with a specific gravity in excess of 13, Tantalum or a Tantalum/Tungsten alloy being preferred. The entire interior of the jacket is left free for the explosive charge; the jacket (102) has increased mechanical, structural and tensile characteristics over prior art projectiles and the projectile has better rotational ballistic stability in use due to the redistribution of the mass thereof to the periphery.
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Izba Pamieci Kopalni Wujek - Katowice, Poland
in History Museums
MUZEUM - Izba Pamieci Kopalni Wujek
posted by: puczmeloun
location: Śląskie, Poland
date approved: 11/24/2013
last visited: never
Skansen Museum - Pszczyna, Poland
Skansen Museum in Pszczyna
date approved: 11/23/2013
Apartheid Museum - Johannesburg, South Africa
The Apartheid Museum, the first of its kind, illustrates the rise and fall of apartheid. It is a superb example of design, space and landscape offering the international community a unique South African experience.
posted by: denben
location: Gauteng, South Africa
date approved: 11/22/2013
Tyskie Browarium (+ City Museum) - Tychy, Poland
Tyskie Browarium - Museum of Tyskie Brewery (+ City Museum)
date approved: 11/20/2013
Heimatmuseum Schwarzbubenland - Dornach, SO, Switzerland
The museum of local history in Dornach is located in the former church in the town center.
posted by: fi67
location: Espace Mittelland (BE/SO), Switzerland
date approved: 11/18/2013
New Richmond Heritage Center - New Richmond Wisconsin
Twelve building, ten acre history site in New Richmond, WI.
posted by: lenron
location: Wisconsin
date approved: 11/15/2013
Landmark Center, Henning MN
Former clinic now used as a museum and community center.
location: Minnesota
date approved: 11/13/2013
Vallejo Naval & Historical Museum
This History Museum occupies what was once the Vallejo City Hall.
posted by: brwhiz
location: California
date approved: 11/10/2013
Clarence Smit Museum
This History Museum occupies what was the former location of the Ripon Memorial Library.
date approved: 11/8/2013
Hewitt Public School Museum - Hewitt MN
Former school now a regional history museum.
date approved: 11/7/2013
Sanger Depot Museum
This History Museum is housed in the historic Sanger Railroad Depot which has been relocated to the Sanger Civic Center.
date approved: 11/5/2013
Northport Museum - Northport, WA
This is a little museum in a little town, with some interesting history.
posted by: BK-Hunters
location: Washington
date approved: 11/2/2013
last visited: 3/31/2014
West Kern Oil Museum
This History Museum is located in the middle of the oil fields of west Kern County near Bakersfield.
date approved: 11/1/2013
The Coal Mining Museum - Zabrze, Poland
The Coal Mining Museum - GUIDO Mine
location: Świętokrzyskie, Poland
date approved: 10/31/2013
Stevens County Museum, Colville, WA
The museum stands on the grounds of what was once the 7 acre estate of first J.H. Young, then Louis Keller.
Ringkøbing Museum, Ringkøbing - Denmark
Ringkøbing Museum ligger tæt på byens centrum og politistationen - The museum is located close to the center of the town and the police station.
posted by: kallehaugerne
location: Denmark
date approved: 10/29/2013
last visited: 9/4/2014
Museo Casa di Dante - Florence, Italy
The house and museum of the poet Dante Alighieri in the city of Firenze.
posted by: razalas
location: Toscana, Italy
date approved: 10/28/2013
Border Station Museum - 07330 Probstzella/ Thüringen/ Deutschland
Museum of History in Probstzella.
posted by: Bianka11
location: Thüringen, Germany
date approved: 10/27/2013
last visited: 11/6/2013
Lyndenburg Museum, Mpumalanga, South Africa
This museum is best known and the home of 7 terracotta heads from the Early Iron Age (about 490 AD).
posted by: Queens Blessing
location: Mpumalanga, South Africa
date approved: 10/26/2013
The Eskridge Hotel Museum - Wynnewood, OK
The Eskridge Hotel Museum has a terrific display of early Oklahoma life, recreated in an authentic gem of Oklahoma history.
posted by: hamquilter
location: Oklahoma
date approved: 10/23/2013
The Postage Stamp Museum - Vaduz, Liechtenstein
The Postage Stamp Museum in Vaduz
location: Liechtenstein
date approved: 10/22/2013
last visited: 6/8/2014
Liechtenstein National Museum - Vaduz, Liechtenstein
Liechtenstein National Museum in Vaduz
last visited: 8/17/2014
Weed Historic Lumber Town Museum - Weed, CA
The Weed Historic Lumber Town Museum located at 303 Gilman in Weed.
posted by: Volcanoguy
date approved: 10/19/2013
last visited: 9/12/2013
Walt Disney Hometown Museum - Marceline, MO
We are located in the historic Santa Fe Depot on Santa Fe Street in beautiful downtown Marceline, Missouri.
posted by: YoSam.
location: Missouri
date approved: 10/18/2013
last visited: 6/14/2014
Stellenbosch Museum, South Africa
This museum features 4-fully furnished "period" homes.
location: Western Cape, South Africa
date approved: 10/17/2013
last visited: 10/21/2014
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Andy Kaufman is 'alive' claims his brother
His brother said he had received a letter from the comedian in 1999
Jess Denham
Jess Denham reports on Arts + Entertainment for The Independent website
Thursday 14 November 2013
The brother of cult comedian Andy Kaufman has claimed the star faked his own death and is still alive.
Renowned for playing Latka Gravas in the 1970s sitcom Taxi, Kaufman officially died from renal failure in 1984 after being diagnosed with cancer at the age of 33.
But at the Andy Kaufman Awards, named in his honour to celebrate young comedy talent, his brother Michael revealed that he had received a letter from Andy in 1999 confirming he was alive.
Michael then introduced a woman who claimed to be the eccentric actor's 24-year-old daughter to the stage.
Kaufman's 'daughter' described him as a "great" father who "just makes us food and takes care of the house".
She said: "He just wanted to be a stay-at-home dad, that's why he wanted to leave the showbiz."
Before the woman took to the stage, Michael described how he had found an essay years ago in which his brother revealed plans to fake his death. A note was included with the essay, stating that the comedian would turn up on Christmas Eve in 1999 at his favourite restaurant.
When Michael visited the restaurant on the designated day, Andy failed to appear, but a waitress handed over a letter saying he had gone into hiding to live a normal, private life with his wife and daughter.
Comedian Killy Dwyer, who was at the award ceremony, wrote on Facebook that "the entire room was freaked out" by the revelations, suggesting that while it "might all be a hoax", the news was "chilling, upsetting and absolutely intriguing".
Kaufman was no stranger to elaborate performance acts, having impersonated Elvis Presley, created a verbally-abusive, rank-smelling alter-ego called Tony Clifton, and organised wrestling matches with women.
Perhaps his best known stunt was hiring 24 buses to take a 2,800 strong audience at Carnegie Hall out for milk and cookies after one of his shows.
As a result, rumours that his death was just another hoax have been circulating for years among his fanbase.
A video from the awards posted on TMZ shows Michael asking the audience not to follow the young woman when she left. "I won't give you her name. I don't even know [her] name. Let her have her privacy," he said.
Kaufman's 'daughter', who would have been born five years after Kaufman's 'official' death, suggested her comedian father will present himself to the public soon.
"I don't know how much longer he can keep everything away," she said to the audience. "He was really thinking about coming. I think something in him needs to come out."
A copy of what is said to be Kaufman's death certificate can be viewed online, stating the comedian died on 16 May, 1984.
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Inscription: The verso of the old mount is annoted in pencil : "19 3/8 x 14 1/2 / Theodor Thomas 3.".Marking: An illegible stamp is repeated twice on the verso of the old mount.
Arthur Ochs Sulzberger ; Donor: Arthur Ochs Sulzberger
Prisco Bagni Il Guercino e il suo Falsario: I Disegni di paesaggio. Bologna, 1985, cat. no. 140, fig. no. 140, p. 170, ill.
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Scotland, Wales and the Republic of Ireland declare interest in hosting Euro 2020
Tuesday 15 May 2012
Scotland, Wales and the Republic of Ireland have formally declared an interest in jointly hosting Euro 2020, as the Celtic nations scent a chance to challenge Turkey for one of sport's three mega events.
The European Championship ranks behind only the World Cup and the Olympics as a major sporting spectacle but interest in the 2020 tournament has been strangely muted.
Until this week, only Turkey had come forward and the prospect of a straight vote against that bid alone has prompted the national associations of Scotland, Wales and Ireland to take a first significant step towards submitting a bid of their own.
The three 'Celtic' FAs have declared an interest in 'tri-hosting' the tournament and UEFA's deadline for such expressions of interest expires at midnight tonight.
The only other country to have come forward is Georgia, but the former Soviet republic would struggle to satisfy UEFA's criteria on the number and quality of stadiums, especially as the tournament will expand from 16 to 24 teams in four years' time.
Turkey at one point looked nailed on to become hosts after being publicly supported by UEFA president Michel Platini but that bid is now in some disarray. The Turkish federation have been engulfed by allegations of corruption and match-fixing in Turkish football, and a Euro 2020 bid conflicts with Istanbul's bid to land the Olympics in the same year.
Platini had signalled he would support Turkey's bid, but only if Istanbul failed in its Olympic bid. UEFA executive committee members much prefer being able to choose between more than one candidate, and having a rival for Euro 2020 also gets the International Olympic Committee out of a hole because they could not vote for Istanbul if Turkey were the only Euro bidder.
One senior figure at UEFA told the Press Association that Turkey have real problems to deal with and that could open the way for the Celtic nations.
He said: "Many in UEFA are losing patience with Turkey due to the chaos in the football there. The Olympic clash does not help either so this could be good news for Scotland, Wales and Ireland if they were to proceed with a bid."
UEFA have had some bad experiences with co-hosting with different governments, different police forces and different tax regimes. The expansion of the tournament means however that very few countries could practically be solo hosts, and England, Germany, and Spain have all ruled themselves out while France are hosting Euro 2016 and Russia are concentrating on the 2018 World Cup. A joint Scandinavian bid also looks unlikely due to a lack of political support.
In geographical terms, Ireland, Scotland and Wales may not have any direct borders with each other but the distances involved are minor compared for example to Ukraine.
Jonathan Ford, the chief executive of the Football Association of Wales, stressed the countries had not yet submitted a bid.
Ford told the Press Association: "It is not a bid, it's a declaration of interest and that will allow us to obtain the information from UEFA so that we can fully assess and determine, independently and together, whether we should submit a bid."
The Football Association of Ireland (FAI) said in a statement: "The expression of interest is preliminary after the principle was discussed and is being put forward by the three associations so that the opportunity can be explored in more detail.
"At this stage no bids would be expected or required by UEFA for at least 18 months."
The Scottish Football Association issued a similar statement saying: "We can confirm that we have had initial discussions on the principle of a joint bid with both Wales and the Republic of Ireland and have declared our interest to UEFA in order that we can fully explore the opportunity in more detail.
"At this stage no bids are expected by UEFA in relation to Euro 2020. These will not be required for at least 18 months."
Bidders would need to put forward up to 10 stadiums to host matches in the Championships. Scotland and Wales would struggle to provide that number of stadiums to satisfy UEFA requirements but Ireland's involvement would cover the shortfall. Somewhat ironically, it was the SFA and FAI who proposed the increase in the size of the competition.
The countries have not fared well in the past in bidding for the tournament. Scotland and the Republic bid jointly for Euro 2008 but were one of the first to be eliminated, and Scotland and Wales considered bidding jointly for Euro 2016 but decided against it.
Georgia have confirmed interest in hosting the tournament despite their hopes of Azerbaijan joining them in a joint bid being dashed.
Lado Vardzelashvili, the Georgian sports minister told a news conference today that they would proceed with a solo bid after Azerbaijan decided to concentrate on a bid by Baku for the 2020 Olympics.
"Azerbaijan has made a bid to host the Olympics so Georgia will continue bidding for Euro 2020 independently," Vardzelashvili was quoted by media in Georgia today.
The former Soviet republic may struggle to fulfil the UEFA criteria for stadiums but Vardzelashvili insisted that construction of "ultra-modern stadiums" will start this year.
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