Patent Application: US-90287501-A

Abstract:
there is provided a uracil substituted 1 - phenylbenzotriazole compound having the structural formula i . also provided are a composition and a method comprising that compound for the control of undesirable plant species . further provided is an intermediate compound useful in the preparation of the compound of formula i .

Description:
surprisingly , it has been discovered that the formula i compounds of this invention are more effective and / or more selective herbicidal agents than the corresponding compounds exemplified in u . s . pat . no . 5 , 523 , 277 wherein q is q 6 . in addition , we have found that the formula i compounds of the present invention are particularly useful for the selective control of undesirable plant species in the presence of crops such as corn , wheat , rice and soybeans . the herbicidal compounds of the present invention are represented by structural formula i . wherein r , r 1 , r 2 , r 6 , a , a 1 and x are as defined above . r 6 is phenyl optionally substituted with any combination of one to three halogen atoms , one to three c 1 - c 8 alkyl groups , one to three c 1 - c 6 alkoxy groups , one c 1 - c 4 alkoxy - c l - c 4 alkyl group , one c 3 - c 7 cycloalkyl group , one or two c 1 - c 6 haloalkyl groups , one c 1 - c 4 alkylthio group , one cyano group , one nitro group , one c ( o ) r 7 group , one co 2 r 8 group , one or two x 4 r 9 groups , one ch = chr 10 group , one ch 2 ch ( r 11 ) r 12 group or one n ( r 13 ) so 2 r 14 group ; r 7 , r 13 , r 14 , r 16 , r 17 , r 18 , r 22 , r 23 , r 26 , r 27 , r 29 and r 30 are each independently hydrogen , c 1 - c 6 alkyl , c 1 - c 6 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl or phenyl ; r 8 , r 21 , r 25 and r 28 are each independently hydrogen , c 1 - c 10 alkyl , c 1 - c 8 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 7 halocycloalkyl , c 3 - c 10 alkenyl , c 3 - c 8 haloalkenyl , c 5 - c 8 cycloalkenyl , c 5 - c 8 halocycloalkenyl , c 3 - c 8 alkynyl , c 3 - c 8 haloalkynyl , benzyl , phenyl , furfuryl , pyridyl , thienyl , oximino , or an alkali metal , alkaline earth metal , manganese , copper , zinc , cobalt , silver , nickel , ammonium or organic ammonium cation ; r 9 is hydrogen , si ( r 15 ) 3 , c ( o ) nr 16 r 17 , c ( o ) r 18 , so 2 r 19 , or c 1 - c 10 alkyl , c 3 - c 10 alkenyl , c 5 - c 8 cycloalkenyl , c 3 - c 8 cycloalkyl , c 3 - c 10 alkynyl , phenyl or benzyl , each of which may optionally be substituted with one to three halogen atoms , one hydroxyl , one benzyloxy , one c 1 - c 6 alkoxy group , one phenoxy group , one oc ( o ) r 20 group , one co2r21 group , one c ( o ) r 22 group , one c ( o ) r 23 r 24 group or one cyano group ; r 10 and r 12 are each independently hydrogen , c 1 - c 6 alkyl , co 2 r 25 , c ( o ) r 26 or c ( o ) nr 27 r 28 ; r 11 is hydrogen , halogen , c 1 - c 6 alkyl , c 1 - c 6 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl , phenyl or cyano ; r 19 is c 1 - c 6 alkyl , c 1 - c 6 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl , phenyl or cyano ; r 24 is hydrogen , c 1 - c 6 alkyl , c 1 - c 6 alkoxy , c 1 - c 6 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , so 2 r 29 , c ( o ) r 30 , benzyl or phenyl ; r 15 and r 20 are each independently c 1 - c 6 alkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl or phenyl ; and r 6 is phenyl optionally substituted with any combination of one to three halogen atoms , one to three c l - c 4 alkyl groups , one to three c 1 - c 4 alkoxy groups , one methoxymethyl group , one c 3 - c 7 cycloalkyl group , or one or two x 4 r 9 groups ; r 9 is c 1 - c 3 alkyl , c 3 - c 6 alkenyl , c 3 - c 8 cycloalkyl , c 3 - c 6 alkynyl , each of which may optionally be substituted with one halogen atom , one c 1 - c 3 alkoxy group , one oc ( o ) r 20 group , one co 2 r 21 group , one c ( o ) r 22 group or one c ( o ) nr 23 r 24 group ; r 20 is c 1 - c 4 alkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl or phenyl ; r 21 is hydrogen , c 1 - c 4 alkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl , phenyl , furfuryl , pyridyl , thienyl , oximino , or an alkali metal , alkaline earth metal , manganese , copper , zinc , cobalt , silver , nickel , ammonium or organic ammonium cation ; r 22 r 23 and r 24 are each independently hydrogen , c 1 - c 4 alkyl , c 1 - c 4 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl or phenyl ; and the term halogen as used in the specification and claims designates chlorine , fluorine , bromine or iodine . the terms haloalkyl and haloalkenyl designate an alkyl group , c n h 2n + 1 , or an alkenyl group , c n h 2n , which contain from one halogen atom to 2n + 1 , or 2n , halogen atoms , respectively . similarly , the term haloalkoxy designates a oc n h 2n + 1 group which contains from one to 2n + 1 halogen atoms . in all cases , the halogen atoms may be the same or different . the formula i compounds of the present invention are effective herbicidal agents useful for the control of a wide variety of undesirable plant species and for controlling weeds native to both dry land and wet land areas . the inventive compounds are effective in controlling the above - said plants when applied to the foliage thereof or to the soil or water containing seeds or other propagating organs thereof such as stolons , tubers or rhizomes , at rates of from 0 . 01 kg / ha to 1 kg / ha . advantageously , it has been found that the compounds of the invention are selective in the presence of soybeans or cereal crops such as corn , wheat and rice when applied preemergence or postemergence . beneficially , the formula i compounds may be used for the selective control of undesirable plant species in transplanted rice culture by applying a herbicidally effective amount of a formula i compound to the soil or water containing the seeds or other propagating organs of said undesirable plant species after the rice has been transplanted . while the compounds of this invention are effective for controlling undesirable plant species when employed alone , they may also be used in combination with or in conjunction with one or more biological chemicals , including herbicides . the compounds of this invention may be applied to the foliage of undesirable plant species or to the soil or water containing seeds or other propagating organs thereof in the form of a solid or liquid herbicidal composition , comprising a herbicidally effective amount of the desired compound dispersed or dissolved in an agronomically acceptable , inert solid or liquid carrier . the compositions may be applied as preemergence or postemergence treatments . the formula i compounds of the present invention may be formulated as emulsifiable concentrates , wettable powders , granular formulations , suspension concentrates , flowable concentrates and the like . formula i compounds wherein a and a 1 , are o may be prepared , as shown in flow diagram i , by reacting an aminobenzotriazole of formula ii with a 2 - dialkylamino - 6h - 1 , 3 - oxazin - 6 - one of formula iii in the presence of an organic acid such as acetic acid to form an intermediate compound of formula iv and reacting the formula iv compound with an electrophile of formula v in the presence of a base such as potassium carbonate . alternatively , intermediate compounds of formula iv may be prepared by reacting an aminobenzotriazole of formula ii with phosgene or an equivalent thereof to form an intermediate isocyanate of formula vi , followed by reaction of said isocyanate vi with an amino - crotonate of formula vii in the presence of a base , as depicted in flow diagram ii . aminobenzotriazoles of formula ii may be prepared as described in u . s . pat . no . 5 , 523 , 277 . formula i compounds wherein a is o and a 1 is s may be prepared , as shown in flow diagram iii , by reacting a formula i compound wherein a and a 1 are o with lawesson &# 39 ; s reagent ( 2 , 4 - bis ( 4 - methoxyphenyl )- 1 , 3 - dithia - 2 , 4 - diphosphetane - 2 , 4 - disulfide ) in the presence of a base such as sodium hydrogen carbonate . formula i compounds wherein a and a 1 are s may be prepared , as shown in flow diagram iv , by reacting a formula i compound wherein a is o and a 1 is s with lawesson &# 39 ; s reagent in the presence of a base . wherein r 1 , r 2 , r 6 , a , a 1 and x are as described hereinabove for formula i . r 6 . is phenyl optionally substituted with any combination of one to three halogen atoms , one to three c 1 - c 8 alkyl groups , one to three c 1 - c 6 alkoxy groups , one c 1 - c 4 alkoxy - c 1 - c 4 alkyl group , one c 3 - c 7 cycloalkyl group , one or two c 1 - c 6 haloalkyl groups , one c 1 - c 4 alkylthio group , one cyano group , one nitro group , one c ( o ) r 7 group , one co 2 r 8 group , one or two x 4 r 9 groups , one ch = chr 10 group , one ch 2 ch ( r 11 ) r 12 group or one n ( r 13 ) so 2 r 14 group ; r 7 , r 13 , r 14 , r 16 , r 17 , r18 r 22 r 23 , r 26 , r 27 , r 29 and r 30 are each independently hydrogen , c 1 - c 6 alkyl , c 1 - c 6 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl or phenyl ; r 8 , r 21 , r 25 and r 28 are each independently hydrogen , c 1 - c 10 alkyl , c 1 - c 8 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 7 halocycloalkyl , c 3 - c 10 alkenyl , c 3 - c 8 haloalkenyl , c 5 - c 8 cycloalkenyl , c 5 - c 8 halocycloalkenyl , c 3 - c 8 alkynyl , c 3 - c 8 haloalkynyl , benzyl , phenyl , furfuryl , pyridyl , thienyl , oximino , or an alkali metal , alkaline earth metal , manganese , copper , zinc , cobalt , silver , nickel , ammonium or organic ammonium cation ; r 9 is hydrogen , si ( r 15 ) 3 , c ( o ) nr 16 r 17 , c ( o ) r 18 , so 2 r 19 , or c 1 - c 10 alkyl , c 3 - c 10 alkenyl , c 5 - c 8 cycloalkenyl , c 3 - c 8 cycloalkyl , c 3 - c 10 alkynyl , phenyl or benzyl , each of which may optionally be substituted with one to three halogen atoms , one hydroxyl , one benzyloxy , one c 1 - c 6 alkoxy group , one phenoxy group , one oc ( o ) r 20 group , one co 2 r 21 group , one c ( o ) r 22 group , one c ( o ) r 23 r 24 group or one cyano group ; r 10 and r 12 are each independently hydrogen , c 1 - c 6 alkyl , co 2 r 25 , c ( o ) r 26 or c ( o ) nr 27 r 28 ; r 11 is hydrogen , halogen , c 1 - c 6 alkyl , c 1 - c 6 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl , phenyl or cyano ; r 19 is c 1 - c 6 alkyl , c 1 - c 6 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl , phenyl or cyano ; r 24 is hydrogen , c 1 - c 6 alkyl , c 1 - c 6 alkoxy , c 1 - c 6 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , so 2 r 29 , c ( o ) r 30 , benzyl or phenyl ; r 15 and r 20 are each independently c 1 - c 6 alkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl or phenyl ; and r 6 is phenyl optionally substituted with any combination of one to three halogen atoms , one to three c 1 - c 4 alkyl groups , one to three c 1 - c 4 alkoxy groups , one methoxymethyl group , one c 3 - c 7 cycloalkyl group , or one or two x 4 r 9 groups ; r 9 c 1 - c 3 alkyl , c 3 - c 6 alkenyl , c 3 - c 8 cycloalkyl , c 3 - c 6 alkynyl , each of which may optionally be substituted with one halogen atom , one c 1 - c 3 alkoxy group , one oc ( o ) r 20 group , one co 2 r 21 group , one c ( o ) r 22 group or one c ( o ) nr 23 r 24 group ; r 20 is c 1 - c 4 alkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl or phenyl ; r 21 hydrogen , c 1 - c 4 alkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl , phenyl , furfuryl , pyridyl , thienyl , oximino , or an alkali metal , alkaline earth metal , manganese , copper , zinc , cobalt , silver , nickel , ammonium or organic ammonium cation ; r 22 r 23 and r 24 are each independently hydrogen , c 1 - c 4 alkyl , c 1 - c 4 haloalkyl , c 3 - c 7 cycloalkyl , c 3 - c 6 alkenyl , c 3 - c 6 alkynyl , benzyl or phenyl ; and most preferred compounds of formula viii are those selected from the group consisting of in order to facilitate a further understanding of the invention , the following examples are presented to illustrate more specific details thereof . the invention is not to be limited thereby except as defined in the claims . the terms 1 h nmr 13 c nmr , and 19 f nmr designate proton , carbon and fluorine nuclear magnetic spectroscopy respectively , and the terms ir and ms designate infrared spectrometry and mass spectroscopy , respectively . to a solution of 5 - fluoro - 1 -( 2 - methoxyphenyl )- 1h - 1 , 2 , 3 - benzotriazol - 6 - amine ( 1 . 0 g , 0 . 0039 mol ) in acetic acid ( 25 ml ) is added 2 -( dimethylamino )- 4 -( trifluoromethyl )- 6h - 1 , 3 - oxazine - 6 - one ( 1 . 1 g , 0 . 005 mol ), and the resulting solution refluxed for ca . 1 hour . the reaction mixture is poured into water , and the resulting solid filtered and dried to afford the title compound as a light tan solid ( 1 . 4 g , 87 %, mp 207 - 211 ° c .) which is characterized by ir and nmr spectral analyses . using essentially the same procedure as described in example 1 and the appropriate amine , the following compounds are obtained . ex . no . r 1 r 2 r 3 r 4 mp (° c .) 2 och 3 h h ch 3 145 - 150 3 h h ch 2 ch 3 h 160 - 164 4 h h ch 3 h 228 - 232 5 ch 3 h h h 145 - 150 6 h ch 3 ch 3 h 222 - 227 7 ch 3 h h och 3 148 - 151 8 ch 3 h och 3 h 104 - 106 9 ch 2 ch 3 h h h 168 - 175 10 ch 2 och 3 h h h 91 - 93 11 h ch 2 och 3 h h 98 - 102 12 h h och 3 h 7200 13 h ch 2 ch 3 h h 160 14 och 3 h h cl 123 15 h h oph h 95 - 105 to a solution of 3 -[ 5 - fluoro - 1 -( 2 - methoxyphenyl )- 1h - 1 , 2 , 3 - benzotriazol - 6 - yl ]- 6 -( trifluoromethyl )- 2 , 4 ( 1h , 3h )- pyrimidinedione ( 1 . 6 g , 0 . 0038 mol ) in dry tetrahydrofuran ( 35 ml ) is added potassium carbonate ( 0 . 07 g , 0 . 005 mol ) followed by dimethylsulfate ( 0 . 48 g , 0 . 005 mol ). after 90 minutes at reflux , additional dimethylsulfate ( 0 . 02 ml , 0 . 0002 mol ) is added . the reaction mixture is then cooled , poured into water and extracted with ethyl acetate . the combined ethyl acetate extracts are dried and concentrated in vacuo , and the residue is chromatographed on silica gel eluting with hexane : ethyl acetate ( 75 : 25 to 50 : 50 ). the title compound is obtained as a white solid ( 1 . 3 g , 81 %, mp 123 - 126 ° c .) which is identified by ir , nmr and mass spectral analyses . using essentially the same procedure as described in example 16 , the following compounds are obtained . ex . no . r 1 r 2 r 3 r 4 mp (° c .) 17 h h ch 2 ch 3 h 189 - 192 18 och 3 h h ch 3 175 - 181 19 h h ch 3 h 167 - 170 20 ch 3 h h h 66 - 68 21 h h ch ( ch 3 ) 2 h 163 - 166 22 ch 3 h h och 3 64 - 67 23 h ch 3 ch 3 h 77 - 87 24 ch 3 h och 3 h 75 - 77 25 ch 2 ch 3 h h h 77 - 87 26 ch 2 och 3 h h h 68 - 70 27 h h och 3 h 216 - 220 28 h ch 2 och 3 ch 2 ch 3 h 62 - 66 29 h ch 2 ch 3 h h 52 - 65 30 och 3 h h cl 96 - 97 to a solution of 3 -[ 5 - fluoro - 1 -( 2 - methoxy - 5 - methylphenyl )- 1h - 1 , 2 , 3 - benzotriazol - 6 - yl ]- 1 - methyl - 6 -( trifluoromethyl )- 2 , 4 ( 1h , 3h )- pyrimidinedione ( 1 . 0 g , 0 . 0022 mol ) in dichloromethane at 10 ° c . is added a solution of boron tribromide ( 1 m , 13 ml , 0 . 013 mol ) in dichloromethane , and the resulting solution refluxed overnight . an additional quantity of boron tribromide ( 5 ml , 0 . 005 mol ) is then added and refluxing continued for 8 hours . the reaction mixture is cooled to room temperature , stirred for several hours , and then poured into water and neutralized with saturated sodium bicarbonate . the organic layer is separated , dried over anhydrous magnesium sulfate , and concentrated in vacuo to a dark solid ( 0 . 75 g ). the residue is purified by flash chromatography on silica gel eluting with hexane : ethyl acetate ( 50 : 50 ) to afford a solid which , after titration with etherhexane , gives the title compound as an off - white solid ( 0 . 44 g , 46 %, mp 248 - 249 ° c . ), which is identified by nmr and mass spectral analyses . in essentially the same manner as described in example 32 , using the appropriate substrate , the following compounds are prepared . ex . no . r 1 r 2 r 3 mp (° c .) 32 ch 3 h oh 108 - 110 33 ch 3 oh h & gt ; 250 3 -[ 5 - fluoro - 1 -( 2 - hydroxy - 5 - methylphenyl )- 1h - 1 , 2 , 3 - benzotriazol - 6 - yl ]- 1 - methyl - 6 - ( trifluoromethyl ) - 2 , 4 ( 1h , 3h )- pyrimidinedione ( 0 . 5 g , 0 . 0011 mol ) is added to dry dimethylformamide ( 5 ml ) followed by methyl bromoacetate ( 0 . 18 g . 0 . 0012 mol ) and potassium carbonate ( 0 . 18 g , 0 . 0013 mol ) . after stirring overnight at room temperature , the reaction mixture is poured into water to give , after drying , the title compound as a white solid ( 0 . 4 g , 71 %, mp 95 - 98 ° c .) which is identified by ir , nmr and mass spectral analyses . using essentially the same procedure as described in example 34 , on the appropriate phenols , the following compounds are obtained . ex . no . r 1 r 2 r 3 mp (° c .) 35 och 2 co 2 ch 3 h h 159 - 164 36 ch 3 h och 2 co 2 ch 2 c ≡ ch 185 - 187 37 ch 3 h och 2 co 2 h 84 38 ch 3 h och 2 co 2 ch 3 72 - 74 39 ch 3 och 2 co 2 ch 3 h 77 - 80 40 och 2 co 2 ch 2 c ≡ ch h ch 3 79 - 84 41 och ( ch 3 ) co 2 ch 3 h ch 3 100 - 105 42 och 2 ch ═ ch 2 h ch 3 133 - 136 43 ch 3 och 2 ch ═ ch 2 h 72 44 h och 2 co 2 h h & gt ; 220 45 h och 2 co 2 ch 3 h 79 - 85 in this evaluation , seedling plants are grown in jiffy flats for about two weeks . the test compounds are dispersed in 80 / 20 acetone / water mixtures containing 1 . 0 % sun - it ® ii , a methylated seed oil , in sufficient quantities to provide the equivalent of about 0 . 006 kg to 0 . 400 kg per hectare of active compound when applied to the plants through a spray nozzle operating at 40 psi for a predetermined time . after spraying , the plants are placed on greenhouse benches and are cared for in accordance with conventional greenhouse procedures . approximately two - three weeks after treatment , the seedling plants are examined and rated according to the rating system set forth below . data obtained are reported in table i below . where more than one test is involved for a given compound , the data are averaged . herbicide rating scale % control rating compared to check 9 100 8 91 - 99 7 80 - 90 6 65 - 79 5 45 - 64 4 30 - 44 3 16 - 29 2 6 - 15 1 1 - 5 0 0 [ 0122 ] plant species employed in herbicidal evaluations header abbr . common name scientific name abuth velvetleaf abutilon theophrasti , medic . ambel ragweed , common ambrosia artemisifolia , l . casob sicklepod cassia obtusifolia , l . cheal lambsquarters , common chenopodium album , l . echog barnyardgrass echinochloa crus - galli , ( l .) beau galap galium galium aparine ipohe morningglory , ivyleaf ipomoea hederacea , ( l .) jacq . setvi foxtail , green setaria viridis , ( l .) beau glxmaw soybean , williams glycine max , ( l .) merr . cv williams trzaw wheat , winter , triticum aestivum , l . unspecified ( winter ) trzawr wheat , winter , triticum aestivum , cv riband cv riband orysat rice , tebonnet oryza sativa , ( l .) zeamx corn , field zea mays , l . ( sammel - bezeichnung ) [ 0123 ] table i postemergence herbicidal evaluation ex rate no . ( kg / ha ) abuth ambel casob cheal galap ipohe echcg setvi glxmaw orysat trzawr zeamx 16 0 . 062 9 . 0 9 . 0 9 . 0 8 . 0 4 . 0 9 . 0 5 . 0 9 . 0 7 . 5 4 . 0 5 . 5 6 . 0 0 . 032 9 . 0 9 . 0 6 . 0 6 . 0 3 . 0 9 . 0 3 . 0 7 . 0 6 . 0 3 . 0 3 . 5 6 . 0 0 . 016 9 . 0 9 . 0 6 . 0 5 . 0 3 . 0 5 . 0 2 . 0 5 . 0 5 . 0 3 . 0 3 . 0 6 . 0 0 . 008 9 . 0 2 . 0 6 . 0 5 . 0 0 . 0 5 . 0 2 . 0 2 . 0 5 . 0 2 . 5 2 . 5 5 . 5 17 0 . 062 9 . 0 9 . 0 6 . 0 9 . 0 7 . 0 9 . 0 5 . 0 8 . 0 7 . 0 4 . 0 5 . 0 5 . 5 0 . 032 9 . 0 8 . 0 5 . 0 7 . 0 4 . 0 9 . 0 1 . 0 3 . 0 5 . 5 3 . 5 4 . 0 5 . 5 0 . 016 9 . 0 6 . 0 3 . 0 6 . 0 4 . 0 9 . 0 0 . 0 1 . 0 5 . 5 3 . 0 3 . 5 5 . 5 0 . 008 9 . 0 5 . 0 1 . 0 9 . 0 2 . 0 9 . 0 0 . 0 1 . 0 5 . 5 3 . 0 3 . 5 5 . 0 18 0 . 062 9 . 0 9 . 0 7 . 0 9 . 0 5 . 0 9 . 0 4 . 0 9 . 0 6 . 0 5 . 5 4 . 5 6 . 0 0 . 032 9 . 0 6 . 0 6 . 0 9 . 0 5 . 0 9 . 0 2 . 0 9 . 0 6 . 5 5 . 5 5 . 5 6 . 0 0 . 016 9 . 0 6 . 0 7 . 0 7 . 0 3 . 0 9 . 0 2 . 0 5 . 0 4 . 5 4 . 0 4 . 5 5 . 5 0 . 008 9 . 0 1 . 0 0 . 0 1 . 0 1 . 0 9 . 0 0 . 0 0 . 0 4 . 5 3 . 5 3 . 5 4 . 5 19 0 . 062 9 . 0 5 . 0 2 . 0 5 . 0 4 . 0 9 . 0 0 . 0 3 . 0 7 . 5 4 . 0 4 . 5 5 . 5 0 . 032 9 . 0 4 . 0 2 . 0 3 . 0 4 . 0 9 . 0 0 . 0 0 . 0 6 . 5 3 . 0 4 . 0 5 . 0 0 . 016 9 . 0 1 . 0 0 . 0 2 . 0 3 . 0 4 . 0 0 . 0 0 . 0 5 . 5 2 . 5 3 . 5 4 . 5 0 . 008 9 . 0 0 . 0 0 . 0 1 . 0 0 . 0 4 . 0 0 . 0 0 . 0 4 . 5 2 . 0 2 . 5 4 . 5 20 0 . 062 9 . 0 3 . 0 1 . 0 5 . 0 9 . 0 9 . 0 0 . 0 0 . 0 5 . 5 1 . 0 2 . 5 5 . 0 0 . 032 9 . 0 1 . 0 0 . 0 3 . 0 2 . 0 4 . 0 0 . 0 0 . 0 5 . 5 0 . 5 1 . 5 3 . 5 0 . 016 9 . 0 1 . 0 0 . 0 0 . 0 0 . 0 4 . 0 0 . 0 0 . 0 5 . 5 0 . 5 1 . 5 3 . 5 0 . 008 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 1 . 0 0 . 0 0 . 0 3 . 0 0 . 0 1 . 5 3 . 0 21 0 . 062 9 . 0 9 . 0 2 . 0 9 . 0 9 . 0 9 . 0 0 . 0 5 . 0 5 . 5 3 . 5 4 . 0 5 . 0 0 . 032 9 . 0 9 . 0 1 . 0 9 . 0 4 . 0 6 . 0 0 . 0 5 . 0 5 . 5 3 . 5 4 . 0 4 . 5 0 . 016 9 . 0 9 . 0 0 . 0 4 . 0 4 . 0 9 . 0 0 . 0 0 . 0 5 . 0 3 . 5 4 . 0 4 . 5 0 . 008 9 . 0 2 . 0 0 . 0 8 . 0 2 . 0 9 . 0 0 . 0 0 . 0 4 . 5 3 . 0 3 . 5 4 . 5 22 0 . 062 9 . 0 3 . 0 0 . 0 4 . 0 5 . 0 2 . 0 0 . 0 0 . 0 5 . 0 3 . 0 4 . 5 4 . 5 0 . 032 9 . 0 2 . 0 0 . 0 3 . 0 3 . 0 9 . 0 0 . 0 0 . 0 4 . 0 3 . 0 4 . 0 4 . 0 0 . 016 9 . 0 0 . 0 0 . 0 9 . 0 0 . 0 2 . 0 0 . 0 0 . 0 4 . 5 2 . 5 3 . 5 4 . 5 0 . 008 9 . 0 0 . 0 0 . 0 9 . 0 0 . 0 2 . 0 0 . 0 0 . 0 4 . 0 2 . 0 3 . 0 4 . 5 23 0 . 062 9 . 0 9 . 0 3 . 0 9 . 0 2 . 0 9 . 0 0 . 0 9 . 0 4 . 5 4 . 0 6 . 5 8 . 5 0 . 032 9 . 0 4 . 0 0 . 0 4 . 0 2 . 0 9 . 0 0 . 0 9 . 0 4 . 5 3 . 5 5 . 5 8 . 0 0 . 016 9 . 0 0 . 0 0 . 0 2 . 0 9 . 0 0 . 0 9 . 0 4 . 5 3 . 0 4 . 5 7 . 0 0 . 008 9 . 0 0 . 0 0 . 0 3 . 0 0 . 0 2 . 0 0 . 0 7 . 0 3 . 5 2 . 5 4 . 0 5 . 5 24 0 . 062 9 . 0 2 . 0 0 . 0 4 . 0 3 . 0 4 . 0 0 . 0 0 . 0 4 . 0 2 . 5 3 . 5 4 . 5 0 . 032 9 . 0 0 . 0 0 . 0 3 . 0 2 . 0 4 . 0 0 . 0 0 . 0 4 . 0 2 . 0 2 . 5 3 . 5 0 . 016 9 . 0 0 . 0 0 . 0 3 . 0 1 . 0 3 . 0 0 . 0 0 . 0 3 . 5 2 . 0 2 . 5 3 . 5 0 . 008 3 . 0 0 . 0 0 . 0 3 . 0 0 . 0 0 . 0 0 . 0 0 . 0 3 . 0 2 . 0 2 . 5 3 . 5 25 0 . 062 9 . 0 2 . 0 1 . 0 9 . 0 4 . 0 9 . 0 0 . 0 7 . 0 6 . 5 2 . 0 3 . 0 5 . 0 0 . 032 9 . 0 2 . 0 0 . 0 9 . 0 4 . 0 9 . 0 0 . 0 3 . 0 5 . 0 1 . 5 3 . 0 4 . 0 0 . 016 8 . 0 0 . 0 0 . 0 9 . 0 0 . 0 3 . 0 0 . 0 0 . 0 4 . 5 1 . 0 2 . 5 3 . 5 0 . 008 6 . 0 0 . 0 0 . 0 3 . 0 0 . 0 2 . 0 0 . 0 0 . 0 3 . 0 0 . 5 1 . 5 3 . 0 26 0 . 062 9 . 0 9 . 0 4 . 0 6 . 0 9 . 0 3 . 0 5 . 0 9 . 0 4 . 5 4 . 0 6 . 5 0 . 032 9 . 0 7 . 0 2 . 0 9 . 0 2 . 0 9 . 0 1 . 0 2 . 0 5 . 5 3 . 0 3 . 0 4 . 0 0 . 016 9 . 0 6 . 0 2 . 0 7 . 0 1 . 0 9 . 0 1 . 0 5 . 0 5 . 0 2 . 0 2 . 5 4 . 0 0 . 008 9 . 0 4 . 0 1 . 0 2 . 0 1 . 0 4 . 0 1 . 0 1 . 0 4 . 5 2 . 0 2 . 0 3 . 5 27 0 . 032 9 . 0 9 . 0 6 . 0 9 . 0 9 . 0 9 . 0 2 . 0 7 . 0 6 . 0 4 . 5 4 . 5 5 . 5 0 . 016 9 . 0 9 . 0 1 . 0 7 . 0 4 . 0 9 . 0 1 . 0 4 . 0 6 . 0 4 . 5 4 . 0 5 . 0 0 . 008 9 . 0 5 . 0 1 . 0 4 . 0 1 . 0 9 . 0 1 . 0 7 . 0 5 . 0 2 . 5 2 . 0 4 . 5 28 0 . 062 9 . 0 9 . 0 3 . 0 9 . 0 8 . 0 9 . 0 1 . 0 9 . 0 6 . 5 5 . 5 5 . 5 7 . 5 0 . 032 9 . 0 9 . 0 1 . 0 7 . 0 6 . 0 9 . 0 1 . 0 7 . 0 6 . 0 3 . 0 4 . 5 6 . 0 0 . 016 9 . 0 9 . 0 0 . 0 4 . 0 4 . 0 9 . 0 0 . 0 3 . 0 5 . 0 2 . 0 4 . 5 6 . 0 0 . 008 9 . 0 9 . 0 0 . 0 2 . 0 4 . 0 9 . 0 0 . 0 0 . 0 4 . 0 0 . 5 2 . 5 3 . 5 29 0 . 062 9 . 0 9 . 0 3 . 0 9 . 0 3 . 0 9 . 0 1 . 0 9 . 0 8 . 0 3 . 0 3 . 0 5 . 0 0 . 032 9 . 0 6 . 0 2 . 0 9 . 0 1 . 0 9 . 0 1 . 0 9 . 0 8 . 0 2 . 0 2 . 5 5 . 0 0 . 016 9 . 0 7 . 0 2 . 0 9 . 0 1 . 0 9 . 0 1 . 0 7 . 0 6 . 5 2 . 0 2 . 0 5 . 0 0 . 008 9 . 0 7 . 0 0 . 0 9 . 0 0 . 0 9 . 0 1 . 0 1 . 0 5 . 0 2 . 0 2 . 0 3 . 5 30 0 . 062 9 . 0 9 . 0 8 . 0 9 . 0 4 . 0 9 . 0 6 . 0 9 . 0 8 . 0 4 . 5 4 . 5 5 . 0 0 . 032 9 . 0 9 . 0 7 . 0 9 . 0 4 . 0 9 . 0 4 . 0 9 . 0 8 . 0 4 . 0 4 . 0 5 . 0 0 . 016 9 . 0 9 . 0 4 . 0 9 . 0 3 . 0 9 . 0 4 . 0 6 . 0 6 . 5 3 . 5 3 . 5 4 . 5 0 . 008 9 . 0 9 . 0 3 . 0 9 . 0 1 . 0 9 . 0 2 . 0 7 . 0 6 . 5 3 . 5 3 . 5 4 . 5 31 0 . 062 4 . 0 3 . 0 0 . 0 0 . 0 0 . 0 4 . 0 3 . 0 5 . 0 5 . 0 1 . 5 3 . 0 4 . 5 0 . 032 2 . 0 0 . 0 0 . 0 0 . 0 0 . 0 4 . 0 0 . 0 0 . 0 4 . 5 1 . 5 3 . 0 4 . 5 0 . 016 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 2 . 0 0 . 0 0 . 0 3 . 5 1 . 0 2 . 0 3 . 5 0 . 008 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 1 . 0 0 . 0 0 . 0 3 . 5 1 . 0 2 . 0 3 . 5 32 0 . 062 4 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 3 . 0 2 . 0 3 . 0 2 . 5 0 . 032 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 3 . 0 1 . 5 2 . 5 2 . 5 0 . 016 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 2 . 5 1 . 5 2 . 5 2 . 5 0 . 008 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 2 . 0 1 . 0 1 . 0 2 . 0 33 0 . 062 5 . 0 0 . 0 0 . 0 2 . 0 0 . 0 9 . 0 0 . 0 0 . 0 5 . 0 2 . 0 2 . 5 4 . 0 0 . 032 3 . 0 0 . 0 0 . 0 0 . 0 0 . 0 3 . 0 0 . 0 0 . 0 4 . 0 0 . 5 2 . 0 3 . 5 0 . 016 3 . 0 0 . 0 0 . 0 0 . 0 0 . 0 2 . 0 0 . 0 0 . 0 3 . 5 0 . 0 1 . 0 3 . 0 0 . 008 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 1 . 5 0 . 0 0 . 5 3 . 0 34 0 . 062 9 . 0 9 . 0 5 . 0 9 . 0 4 . 0 9 . 0 9 . 0 9 . 0 7 . 0 7 . 5 8 . 0 9 . 0 0 . 032 9 . 0 9 . 0 1 . 0 3 . 0 4 . 0 9 . 0 9 . 0 9 . 0 7 . 0 6 . 5 7 . 0 8 . 5 0 . 016 9 . 0 3 . 0 0 . 0 3 . 0 3 . 0 9 . 0 9 . 0 9 . 0 6 . 5 4 . 0 5 . 0 7 . 5 0 . 008 9 . 0 0 . 0 0 . 0 2 . 0 0 . 0 9 . 0 7 . 0 9 . 0 5 . 0 3 . 0 5 . 0 7 . 0 35 0 . 062 9 . 0 9 . 0 2 . 0 7 . 0 4 . 0 9 . 0 9 . 0 8 . 0 7 . 5 7 . 0 7 . 0 7 . 5 0 . 032 9 . 0 9 . 0 2 . 0 6 . 0 3 . 0 9 . 0 7 . 0 9 . 0 6 . 0 6 . 0 5 . 5 5 . 5 0 . 016 5 . 0 5 . 0 1 . 0 4 . 0 1 . 0 4 . 0 4 . 0 9 . 0 4 . 5 3 . 5 3 . 0 4 . 5 0 . 008 5 . 0 4 . 0 1 . 0 1 . 0 1 . 0 9 . 0 2 . 0 1 . 0 5 . 0 3 . 0 3 . 5 5 . 0 36 0 . 062 9 . 0 5 . 0 0 . 0 4 . 0 3 . 0 9 . 0 3 . 0 9 . 0 4 . 5 4 . 0 7 . 0 8 . 5 0 . 032 9 . 0 5 . 0 0 . 0 2 . 0 2 . 0 9 . 0 0 . 0 7 . 0 4 . 0 2 . 5 6 . 0 8 . 0 0 . 016 7 . 0 4 . 0 0 . 0 0 . 0 0 . 0 8 . 0 0 . 0 4 . 0 4 . 0 1 . 0 5 . 0 7 . 5 0 . 008 2 . 0 2 . 0 0 . 0 0 . 0 0 . 0 5 . 0 0 . 0 4 . 0 3 . 5 1 . 5 4 . 5 7 . 5 37 0 . 062 9 . 0 9 . 0 0 . 0 4 . 0 2 . 0 9 . 0 3 . 0 9 . 0 7 . 0 7 . 5 7 . 0 8 . 0 0 . 032 5 . 0 9 . 0 0 . 0 4 . 0 0 . 0 9 . 0 2 . 0 7 . 0 6 . 5 3 . 5 5 . 5 7 . 5 0 . 016 3 . 0 4 . 0 0 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 4 . 0 1 . 0 5 . 5 7 . 5 0 . 008 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 3 . 0 0 . 0 0 . 0 3 . 5 0 . 5 3 . 5 7 . 0 38 0 . 062 9 . 0 9 . 0 1 . 0 3 . 0 4 . 0 9 . 0 3 . 0 9 . 0 7 . 5 6 . 0 8 . 0 8 . 0 0 . 032 9 . 0 7 . 0 0 . 0 2 . 0 3 . 0 9 . 0 3 . 0 7 . 0 6 . 0 3 . 5 6 . 0 8 . 0 0 . 016 8 . 0 7 . 0 0 . 0 0 . 0 0 . 0 5 . 0 0 . 0 0 . 0 5 . 5 2 . 0 4 . 5 8 . 0 0 . 008 3 . 0 2 . 0 0 . 0 0 . 0 0 . 0 5 . 0 0 . 0 0 . 0 5 . 5 1 . 0 3 . 5 7 . 5 39 0 . 062 9 . 0 7 . 0 2 . 0 7 . 0 3 . 0 9 . 0 3 . 0 2 . 0 5 . 0 4 . 0 5 . 5 7 . 5 0 . 032 9 . 0 6 . 0 0 . 0 2 . 0 3 . 0 9 . 0 0 . 0 0 . 0 4 . 0 1 . 0 3 . 5 7 . 5 0 . 016 9 . 0 0 . 0 0 . 0 2 . 0 0 . 0 8 . 0 0 . 0 0 . 0 3 . 5 0 . 5 3 . 0 7 . 5 0 . 008 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 3 . 5 0 . 0 2 . 5 7 . 0 40 0 . 062 9 . 0 7 . 0 6 . 0 9 . 0 5 . 0 9 . 0 9 . 0 9 . 0 7 . 0 6 . 5 6 . 5 8 . 5 0 . 032 9 . 0 9 . 0 3 . 0 7 . 0 2 . 0 9 . 0 9 . 0 9 . 0 6 . 5 5 . 0 5 . 5 7 . 5 0 . 016 9 . 0 7 . 0 1 . 0 3 . 0 2 . 0 9 . 0 9 . 0 9 . 0 6 . 0 5 . 0 5 . 0 7 . 5 0 . 008 9 . 0 9 . 0 1 . 0 4 . 0 1 . 0 9 . 0 4 . 0 6 . 0 5 . 5 4 . 0 4 . 0 5 . 0 41 0 . 062 9 . 0 9 . 0 9 . 0 5 . 0 3 . 0 9 . 0 9 . 0 9 . 0 8 . 0 8 . 0 8 . 0 9 . 0 0 . 032 9 . 0 9 . 0 4 . 0 4 . 0 3 . 0 9 . 0 9 . 0 9 . 0 8 . 0 7 . 0 8 . 0 8 . 0 0 . 016 9 . 0 9 . 0 3 . 0 2 . 0 1 . 0 9 . 0 9 . 0 9 . 0 7 . 5 2 . 5 7 . 0 8 . 0 0 . 008 9 . 0 7 . 0 1 . 0 2 . 0 0 . 0 9 . 0 6 . 7 . 0 5 . 5 1 . 5 6 . 0 6 . 5 42 0 . 062 9 . 0 9 . 0 4 . 0 7 . 0 1 . 0 9 . 0 1 . 0 9 . 0 7 . 0 2 . 5 4 . 0 5 . 0 0 . 032 9 . 0 7 . 0 4 . 0 7 . 0 1 . 0 9 . 0 1 . 0 9 . 0 7 . 0 2 . 5 3 . 0 4 . 5 0 . 016 9 . 0 7 . 0 0 . 0 6 . 0 1 . 0 9 . 0 1 . 0 2 . 0 5 . 5 2 . 5 2 . 5 5 . 0 0 . 008 7 . 0 7 . 0 0 . 0 2 . 0 1 . 0 9 . 0 0 . 0 0 . 0 5 . 0 2 . 0 2 . 5 5 . 0 43 0 . 062 9 . 0 9 . 0 3 . 0 4 . 0 1 . 0 9 . 0 2 . 0 9 . 0 5 . 5 3 . 0 3 . 0 5 . 0 0 . 032 9 . 0 7 . 0 0 . 0 3 . 0 1 . 0 9 . 0 1 . 0 9 . 0 5 . 5 2 . 0 3 . 0 5 . 0 0 . 016 9 . 0 7 . 0 0 . 0 3 . 0 0 . 0 9 . 0 1 . 0 1 . 0 5 . 0 2 . 0 3 . 0 5 . 0 0 . 008 9 . 0 1 . 0 0 . 0 0 . 0 0 . 0 9 . 0 1 . 0 0 . 0 5 . 0 2 . 5 3 . 0 4 . 0 44 0 . 062 9 . 0 7 . 0 2 . 0 9 . 0 2 . 0 9 . 0 6 . 0 7 . 0 7 . 0 3 . 0 4 . 0 7 . 0 0 . 032 7 . 0 6 . 0 1 . 0 6 . 0 1 . 0 9 . 0 6 . 0 7 . 0 6 . 5 2 . 5 3 . 5 6 . 5 0 . 016 9 . 0 3 . 0 0 . 0 7 . 0 0 . 0 7 . 0 4 . 0 4 . 0 6 . 5 2 . 5 4 . 0 6 . 5 0 . 008 9 . 0 3 . 0 0 . 0 5 . 0 0 . 0 7 . 0 3 . 0 4 . 0 5 . 0 2 . 5 3 . 0 4 . 5 45 0 . 062 9 . 0 9 . 0 5 . 0 7 . 0 3 . 0 9 . 0 9 . 0 9 . 0 8 . 0 3 . 5 8 . 0 9 . 0 0 . 032 9 . 0 7 . 0 4 . 0 7 . 0 1 . 0 9 . 0 8 . 0 9 . 0 8 . 0 2 . 0 6 . 0 8 . 0 0 . 016 9 . 0 3 . 0 0 . 0 4 . 0 0 . 0 9 . 0 5 . 0 8 . 0 6 . 5 1 . 0 6 . 0 8 . 0 0 . 008 9 . 0 2 . 0 0 . 0 2 . 0 0 . 0 9 . 0 0 . 0 3 . 0 6 . 0 0 . 5 4 . 0 7 . 5 the preemergence herbicidal activity of the test compounds of the present invention is exemplified by the following tests in which the seeds of a variety of monocotyledonous and dicotyledonous plants are separately mixed with potting soil and planted on top of approximately one inch of soil in separate pint cups . after planting , the cups are sprayed with the selected aqueous acetone solution containing test compound in sufficient quantity to provide the equivalent of about 0 . 013 to 0 . 800 kg per hectare of test compound per cup . the treated cups are then placed on greenhouse benches , watered and cared for in accordance with conventional greenhouse procedures . from four to five weeks after treatment , the tests are terminated and each cup is examined and rated according to the rating system provided in example 46 . the data obtained are reported in table ii below . table ii preemergence herbicidal evaluation ex . rate no . ( kg / ha ) abuth ambel casob cheal galap ipohe echcg setvi glxmaw orysat trzawr zeamx 16 0 . 125 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 8 . 0 0 . 062 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 8 . 0 8 . 0 0 . 032 9 . 0 9 . 0 0 . 0 9 . 0 0 . 0 3 . 0 9 . 0 9 . 0 9 . 0 7 . 0 8 . 0 7 . 0 0 . 016 9 . 0 6 . 0 0 . 0 9 . 0 0 . 0 3 . 0 9 . 0 9 . 0 9 . 0 7 . 0 6 . 0 8 . 0 17 0 . 125 9 . 0 8 . 3 2 . 3 9 . 0 1 . 0 9 . 0 8 . 3 9 . 0 3 . 0 4 . 7 6 . 7 0 . 062 9 . 0 6 . 7 3 . 3 9 . 0 1 . 0 6 . 0 6 . 3 9 . 0 3 . 0 4 . 0 3 . 0 4 . 0 0 . 032 7 . 0 3 . 3 1 . 3 9 . 0 0 . 0 3 . 3 1 . 7 7 . 3 1 . 7 0 . 5 3 . 7 0 . 016 9 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 6 . 5 1 . 5 1 . 0 1 . 0 18 0 . 125 9 . 0 8 . 0 5 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 6 . 0 7 . 0 8 . 5 0 . 062 9 . 0 9 . 0 0 . 5 9 . 0 5 . 0 8 . 0 9 . 0 9 . 0 7 . 5 6 . 0 6 . 0 7 . 0 0 . 032 9 . 0 6 . 0 0 . 0 9 . 0 1 . 0 9 . 0 8 . 0 9 . 0 4 . 5 6 . 0 3 . 0 5 . 0 0 . 016 6 . 0 4 . 0 2 . 5 9 . 0 7 . 5 6 . 0 9 . 0 3 . 0 3 . 0 2 . 0 5 . 0 19 0 . 125 9 . 0 9 . 0 1 . 0 9 . 0 9 . 0 8 . 0 9 . 0 9 . 0 4 . 0 2 . 0 3 . 0 6 . 5 0 . 062 9 . 0 8 . 0 1 . 5 9 . 0 0 . 0 5 . 5 7 . 0 9 . 0 2 . 5 1 . 5 2 . 0 4 . 0 0 . 032 6 . 5 5 . 5 1 . 5 9 . 0 0 . 0 1 . 5 4 . 0 7 . 0 1 . 5 0 . 5 1 . 0 1 . 5 0 . 016 1 . 0 4 . 5 1 . 0 9 . 0 0 . 0 1 . 0 0 . 5 4 . 5 0 . 5 0 . 0 0 . 0 1 . 0 20 0 . 125 9 . 0 5 . 5 2 . 0 9 . 0 0 . 0 4 . 5 8 . 0 9 . 0 3 . 0 3 . 0 6 . 0 6 . 0 0 . 062 9 . 0 2 . 5 0 . 0 9 . 0 0 . 0 4 . 5 3 . 5 9 . 0 1 . 5 1 . 0 4 . 0 4 . 5 0 . 032 6 . 5 1 . 5 0 . 0 9 . 0 0 . 0 3 . 0 0 . 0 8 . 0 0 . 5 0 . 0 0 . 0 1 . 0 0 . 016 0 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 21 0 . 125 9 . 0 7 . 5 2 . 0 9 . 0 0 . 0 3 . 5 3 . 5 9 . 0 1 . 0 0 . 0 1 . 0 3 . 5 0 . 062 6 . 0 3 . 5 1 . 5 9 . 0 0 . 0 2 . 0 1 . 0 6 . 5 0 . 5 0 . 0 0 . 0 1 . 0 0 . 032 4 . 5 3 . 0 0 . 0 9 . 0 0 . 0 1 . 5 0 . 0 2 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 016 0 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 22 0 . 125 7 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 7 . 0 9 . 0 0 . 0 0 . 0 4 . 0 6 . 0 0 . 062 9 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 2 . 0 7 . 0 0 . 0 0 . 0 2 . 0 4 . 0 0 . 032 9 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 2 . 0 0 . 0 0 . 0 1 . 0 2 . 0 0 . 016 0 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 23 0 . 125 9 . 0 1 . 0 0 . 0 9 . 0 0 . 0 1 . 0 8 . 0 9 . 0 0 . 0 0 . 0 3 . 0 4 . 0 0 . 062 9 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 5 . 0 9 . 0 0 . 0 0 . 0 1 . 0 0 . 0 0 . 032 3 . 0 0 . 0 0 . 0 7 . 0 0 . 0 0 . 0 2 . 0 8 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 016 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 3 . 0 0 . 0 0 . 0 0 . 0 0 . 0 24 0 . 125 9 . 0 0 . 0 0 . 0 9 . 0 0 . 0 7 . 0 9 . 0 5 . 0 1 . 0 1 . 0 6 . 0 0 . 062 9 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 3 . 0 9 . 0 2 . 0 1 . 0 1 . 0 4 . 0 0 . 032 6 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 1 . 0 0 . 0 0 . 0 0 . 0 0 . 016 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 25 0 . 125 9 . 0 3 . 5 2 . 0 9 . 0 0 . 0 6 . 5 8 . 0 9 . 0 1 . 5 1 . 5 2 . 0 4 . 0 0 . 062 6 . 0 1 . 0 1 . 5 9 . 0 0 . 0 5 . 5 2 . 0 9 . 0 2 . 0 0 . 0 0 . 0 2 . 0 0 . 032 6 . 0 0 . 0 0 . 0 9 . 0 0 . 0 4 . 5 0 . 0 3 . 5 0 . 0 0 . 0 0 . 0 0 . 0 0 . 016 3 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 26 0 . 125 9 . 0 9 . 0 7 . 0 9 . 0 8 . 0 9 . 0 9 . 0 9 . 0 5 . 0 7 . 0 8 . 0 7 . 0 0 . 062 9 . 0 7 . 0 7 . 0 9 . 0 7 . 0 6 . 0 7 . 0 9 . 0 9 . 0 5 . 0 6 . 0 7 . 0 0 . 032 9 . 0 7 . 0 0 . 0 7 . 0 0 . 0 9 . 0 6 . 0 9 . 0 2 . 0 3 . 0 4 . 0 0 . 016 9 . 0 2 . 0 0 . 0 0 . 0 0 . 0 1 . 0 2 . 0 1 . 0 0 . 0 0 . 0 1 . 0 27 0 . 125 9 . 0 9 . 0 9 . 0 9 . 0 9 . 0 5 . 0 9 . 0 9 . 0 9 . 0 6 . 0 2 . 0 7 . 0 0 . 062 9 . 0 7 . 0 2 . 0 9 . 0 9 . 0 1 . 0 9 . 0 9 . 0 5 . 0 5 . 0 3 . 0 7 . 0 0 . 032 6 . 0 2 . 0 1 . 0 9 . 0 2 . 0 1 . 0 4 . 0 9 . 0 1 . 0 2 . 0 2 . 0 4 . 0 0 . 016 0 . 0 0 . 0 9 . 0 1 . 0 0 . 0 1 . 0 9 . 0 1 . 0 1 . 0 1 . 0 2 . 0 28 0 . 125 9 . 0 7 . 0 9 . 0 9 . 0 1 . 0 7 . 0 9 . 0 0 . 0 0 . 0 0 . 0 5 . 0 0 . 062 9 . 0 1 . 0 0 . 0 9 . 0 0 . 0 1 . 0 0 . 0 4 . 0 0 . 0 0 . 0 0 . 0 4 . 0 0 . 032 2 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 2 . 0 0 . 0 0 . 0 0 . 0 3 . 0 0 . 016 0 . 0 0 . 0 3 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 29 0 . 125 9 . 0 7 . 0 1 . 0 9 . 0 8 . 0 7 . 0 7 . 0 9 . 0 5 . 0 4 . 0 2 . 0 5 . 0 0 . 062 9 . 0 3 . 0 9 . 0 1 . 0 6 . 0 7 . 0 9 . 0 4 . 0 3 . 0 2 . 0 4 . 0 0 . 032 9 . 0 0 . 0 9 . 0 0 . 0 3 . 0 4 . 0 9 . 0 1 . 0 1 . 0 1 . 0 2 . 0 0 . 016 6 . 0 0 . 0 1 . 0 9 . 0 0 . 0 0 . 0 2 . 0 6 . 0 0 . 0 0 . 0 1 . 0 0 . 0 30 0 . 125 6 . 0 6 . 0 2 . 0 9 . 0 4 . 0 3 . 0 7 . 0 9 . 0 2 . 0 4 . 0 2 . 0 7 . 0 0 . 062 3 . 0 0 . 0 9 . 0 3 . 0 4 . 0 7 . 0 9 . 0 1 . 0 2 . 0 2 . 0 5 . 0 0 . 032 0 . 0 1 . 0 9 . 0 2 . 0 0 . 0 5 . 0 7 . 0 1 . 0 1 . 0 1 . 0 3 . 0 0 . 016 0 . 0 0 . 0 0 . 0 9 . 0 2 . 0 0 . 0 1 . 0 4 . 0 1 . 0 0 . 0 0 . 0 1 . 0 31 0 . 125 3 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 062 0 . 0 0 . 0 0 . 0 3 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 032 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 016 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 008 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 32 0 . 125 4 . 0 0 . 0 0 . 0 6 . 0 0 . 0 0 . 0 0 . 0 1 . 0 0 . 0 0 . 0 1 . 0 0 . 062 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 032 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 016 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 33 0 . 125 9 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 062 0 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 032 0 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 016 0 . 0 0 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 34 0 . 125 9 . 0 8 . 0 6 . 0 9 . 0 7 . 0 9 . 0 7 . 5 9 . 0 2 . 0 5 . 0 3 . 0 4 . 0 0 . 062 9 . 0 6 . 0 2 . 5 9 . 0 0 . 0 5 . 0 5 . 0 9 . 0 1 . 5 3 . 0 1 . 0 3 . 5 0 . 032 9 . 0 5 . 0 2 . 0 9 . 0 0 . 0 9 . 0 2 . 0 6 . 0 1 . 0 2 . 5 1 . 0 0 . 5 0 . 016 9 . 0 1 . 0 9 . 0 0 . 0 4 . 0 7 . 0 1 . 0 1 . 0 1 . 0 0 . 0 35 0 . 125 5 . 5 5 . 0 2 . 0 9 . 0 5 . 0 9 . 0 4 . 5 9 . 0 2 . 5 6 . 0 1 . 0 3 . 0 0 . 062 9 . 0 3 . 5 4 . 0 9 . 0 0 . 0 5 . 0 2 . 0 6 . 5 1 . 5 3 . 5 1 . 0 1 . 0 0 . 032 4 . 0 0 . 0 0 . 0 9 . 0 0 . 0 4 . 5 0 . 0 1 . 5 0 . 0 0 . 0 0 . 0 0 . 0 0 . 016 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 1 . 0 0 . 0 0 . 0 0 . 0 36 0 . 125 8 . 0 5 . 0 0 . 0 9 . 0 0 . 0 4 . 0 0 . 0 3 . 0 0 . 0 1 . 5 0 . 0 0 . 0 0 . 062 3 . 0 2 . 0 0 . 0 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 1 . 0 0 . 0 0 . 0 0 . 032 1 . 5 2 . 0 0 . 0 6 . 5 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 016 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 37 0 . 125 9 . 0 3 . 0 0 . 0 9 . 0 0 . 0 5 . 0 0 . 0 8 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 062 9 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 0 . 0 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