Patent Application: US-48526583-A

Abstract:
there is provided a new class of derivatives of 2 - nitro - 5 - benzoyl compounds that have pre - and post - emergence herbicidal activity . the derivatives include certain substituted phenyl esters , phenyl thioesters ; heterocyclic esters ; substituted alkyl and alkylthio esters ; carbonates and thiocarbonates ; benzoyl phosphonates ; substituted alkanones and substituted amides .

Description:
the specific 2 - nitro - 5 -( substituted - phenoxy ) benzoyl compounds are described below . one method for preparing these compounds is the use of the ullman ether synthesis reaction between the alkali metal ( e . g ., na , k ) salt of a suitable substituted phenol , e . g ., m - hydroxy benzoic acid or m - cresol with an active halogen - substituted aromatic , e . g ., 3 , 4 - dichlorobenzotrifluoride . the intermediate obtained may be nitrated and subsequently derivatized by known procedures to the desired benzoyl compound . where m - cresol is used as a starting material , the product obtained can be oxidized and subsequently nitrated before the aforementioned derivatization . illustrative compounds of this class are those of the formula : ## str2 ## where x is selected from no 2 ; lower alkyl of c 1 - 4 ; halogen ; phenyl ; coor where r is lower alkyl of c 1 - 4 , h or a cation selected from alkali metals , alkaline earth metals , ammonium and lower alkyl and di - lower alkyl ammonium ; cn ; lower alkyl thio of c 1 - 4 ; lower alkoxy of c 1 - 4 ; trifluoromethyl ; and combinations thereof . x can be hydrogen when q is sulfur . to a stirred solution of 2 , 4 - dinitro - 6 - sec - butylphenol ( 3 . 60 g , 0 . 015 mole ) and 5 -[- 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl chloride ( 5 . 68 g , 0 . 015 mole ) in toluene ( 25 ml ) was added triethylamine ( 1 . 50 g , 0 . 015 mole ). the temperature exothermed to 45 ° c . and there was an immediate precipitation of triethylamine hydrochloride . the reaction was stirred and heated to 110 ° f . for 15 hours . the precipitate was filtered from the cooled solution , washed and dried to give triethylamine hydrochloride ( 1 . 8 g ). the toluene solution was washed with 10 % sodium hydroxide ( 3 × 25 ml ). the toluene was then stripped off on a rotary evaporator to give 5 . 5 g ( 62 %) of a crude brown oil which slowly crystallized . recrystallization from methanol gave 2 . 1 g of an off white solid , mp . 109 °- 110 ° c . nmr ( d6 acetone ): triplet 0 . 9 ppm ( 3h , j = 7 . 0 hz ): doublet 1 . 37 ppm ( 3h , j = 7 . 0 hz ): multiplet 1 . 82 ppm ( 2h ); multiplet 3 . 35 ppm ( 1h ); multiplet 7 . 5 - 8 . 2 ( 5h ); doublet 8 . 45 ppm ( 1h , j = 9 . 0 hz ); doublet 8 . 82 ppm ( 1h , j = 2 . 4 hz ); doublet 9 . 02 ppm ( 1h , j = 2 . 4 hz ). in a similar manner the following compounds were prepared as defined according to formula ii : ______________________________________ q phenyl substitutioncompound ( o or s ) x . sub . n m . p ., ° c . ______________________________________2 o 2 - no . sub . 2 137 - 93 o 3 - no . sub . 2 93 . 54 o 4 - no . sub . 2 115 - 75 o 5 - ch . sub . 3 -- 2no . sub . 2 88 - 906 o 2 - cl -- 4no . sub . 2 99 - 1017 o 4 - cl 135 - 78 o 4 - cl -- 2 - ch . sub . 3 121 - 29 o 2 - cl -- 4 - ch . sub . 3 105 - 710 o 2 - cl -- 4 - phenyl 128 - 3011 o 2 , 4 -( cl ). sub . 2 144 - 712 o 4 - cooch . sub . 3 103 - 613 o 4 - cn 103 - 514 o 4 - sch . sub . 3 94 - 515 o 3 - och . sub . 3 95 - 716 o 4 - och . sub . 3 128 - 917 o 3 - cf . sub . 3 oil18 o 4 - coona 215 - 2019 o 4 - cooh 191 - 820 s h oil21 s 4 - cl 128 - 3022 s 4 - ch . sub . 3 90 - 323 s 4 - och . sub . 3 oil24 s 3 , 4 -( cl ). sub . 2 oil______________________________________ ______________________________________ ## str3 ## compound______________________________________ ## str4 ## 2 , 6 - diethylphenyl 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenyoxy ]- 2 - nitrobenzoate ## str5 ## s [ 2 - carboxyphenyl ) 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzenecarbothioate ## str6 ## 4 - cyano - 2 , 6 - dibromophenyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str7 ## 3 , 6 - dichloro - 2 - methoxycarbonyl - phenyl 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str8 ## ( 2 , 6 - di - 6 - butyl ) phenyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str9 ## pentachlorophenyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate______________________________________ illustrative compounds of this class are those of the formula : ## str10 ## where q is o or s and het is a substituted or unsubstituted heterocyclic ring of 5 to 7 members comprising carbon in combination with one or more of sulfur , oxygen and nitrogen where a carbon atom on the ring is bound directly to q . preparation of 3 - pyridyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate : to a stirred solution of 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl chloride ( 3 . 79 g , 0 . 01 mole ) and triethyl amine ( 1 . 01 g , 0 . 01 mole ) in toluene ( 50 ml ) was added 3 - hydroxypyridine ( 0 . 95 g , 0 . 01 mole ). the temperature exothermed to 33 ° c . and there was an immediate precipitate . the reaction was then refluxed for 24 hours , cooled to room temperature and the triethylamine hydrochloride precipitate collected by filtration . the toluene solution was washed with dilute sodium hydroxide solution and then with saturated sodium chloride solution . after drying and evaporation of the solvent there was obtained 3 . 1 g of brown oil which solidified . this was triturated with hexane and the solid filtered and dried to give a tan product , m . p . 65 °- 68 ° c . nmr ( d 6 - acetone ): complex multiplet 7 . 2 - 8 . 1 ppm ( 7h ); doublet 8 . 50 ppm ( 1h , j = 4 . 5 hz ); multiplet 8 . 75 ppm ( 2h ). this compound is defined in accordance with formula iii as &# 34 ; q &# 34 ; is o and &# 34 ; het &# 34 ; is ## str11 ## the compound was prepared by the procedure shown for compound 25 . compound 26 has an m . p . of 153 °- 161 ° c . ______________________________________qhet compound name______________________________________ ## str12 ## 3 -( 1 , 2 , 5 thiadiazoloyl )- 5 -[ 2 - chloro - 4 - trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str13 ## 1 , 2 - dihydro - 1 , 6 - dimethyl - 2 - oxo 4 - pyridinyl 5 -[ 2 - chloro - 4 - trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str14 ## 6 ( 2 , 3 - dihydro - 3 - oxo - pyridazinyl ) 5 -[ 2 - chloro - 4 -( trifluorom ethyl ) phenoxy ]- 2 - nitrobenzoate ## str15 ## 2 - chloro - 6 - pyridinyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str16 ## s -( 2 , 6 - dichloro - 4 - s - triazinyl ) 5 -[ 2 - chloro - 4 -( trifluoromet hyl ) phenoxy ]- 2 - nitrobenzoate ## str17 ## s ( 2 - methyl 1 , 3 , 4 ,- thiadiazol - 5 - yl ) 5 -[ 2 - chloro - 4 - trifluo ro - methyl ) phenoxy ]- 2 - nitrobenzene - carbothioate ## str18 ## s ( 2 - pyridinyl ) 5 -[- 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzenecarbothioate noxide ## str19 ## s [ 4 - methyl - 3 - thioxo - 3h1 , 2 - dithiol - 5 - yl ] 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzene - carbothioate ## str20 ## s [ 3 , 5 - bis -( diethylamino )- s - tri - azinyl ] 5 -[ 2 - chloro - 4 -( tri fluoro - methyl ) phenoxy ]- 2 - nitrobenzene - carbothioate______________________________________ illustrative compounds of this class are those of the formula : ## str21 ## wherein the substituents on the straight or branched c 1 - 4 alkyl group are selected from cyano ; phenyl ; ## str22 ## where n is 1 to 5 and x is selected from no 2 , lower alkyl or c 1 - 4 , halogen , phenyl , cn , lower alkyl thio of c 1 - 4 , lower alkoxy of c 1 - 4 , trifluoromethyl and combinations thereof ; ## str23 ## phenoxy ; nitro ; sr 1 ; sor 1 ; so 2 r 1 ; where r 1 is an alkyl of 1 to 3 carbons and r 2 is an alkyl or alkenyl of up to 3 carbons and wherein one or more of said substituents can be attached to any one or more of the carbons on said straight or branched c 1 - 4 alkyl group . the compounds of this class may be prepared by the methods shown above or alternatively by displacement of an active halogen ( e . g ., haloalkyl x ) with the salt of an acid ( e . g ., ## str24 ## the following substituted c 1 - 4 alkyl esters as defined by formula iv were prepared : ______________________________________compound substituted alkyl group m . p . ° c . ______________________________________27 c ( ch . sub . 3 ). sub . 2 cn oil28 ch ( ch . sub . 3 ) cn oil29 ch . sub . 2 coch . sub . 3 83 - 530 ## str25 ## oil 31 ## str26 ## oil 32 ## str27 ## oil 33 ## str28 ## oil 34 ch . sub . 2ch . sub . 2cn oil35 36 ## str29 ## 86 - 8 37 ## str30 ## 112 - 3 38 ch . sub . 2 c ( ch . sub . 3 ). sub . 2no . sub . 2 oily semisolid39 ch . sub . 2ch . sub . 2sch . sub . 3 oil40 ch . sub . 2ch . sub . 2so . sub . 2 ch . sub . 3 97 - 9______________________________________ ______________________________________substituted alkyl compound name______________________________________ch . sub . 2sch . sub . 2 ch . sub . 3 ( ethylthio ) methyl 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitro - benzoate ## str31 ## ( ethylsulfinyl ) methyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitro - benzoate ## str32 ## ( ethylsulfinyl ) methyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str33 ## 1 - acetylethyl 5 -[ 2 - chloro - 4 - tri - fluoromethyl ) phenoxy ]- 2 - nitro - benzoate ## str34 ## 3 - acetylpropyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - n itrobenzoate ## str35 ## 2 -( methylsulfinyl ) ethyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str36 ## ( 3 - fluorophenyl ) methyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate______________________________________ illustrative compounds of this class are those of the formula : ## str37 ## where q is o or s and y is a straight or branched alkoxy or alkylthio of 1 to 6 carbons , a dialkylamino of 2 to 6 carbons , or a heterocyclic amine such as morpholine . to a stirred solution of 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoic acid ( 3 . 0 g , 0 . 0083 mole ) in ether ( 15 ml ) was added triethylamine ( 0 . 84 g , 0 . 0083 mole ). a precipitate formed . the reaction was cooled to 4 ° c . and a solution of ethylchlorothioformate ( 1 . 03 g , 0 . 0083 mole ) in ether was added dropwise . cooling was maintained during initial exotherm . the reaction was then stirred at room temperature for twenty hours . the precipitate of triethyl amine hydrochloride was filtered . the ether was washed consecutively with 10 % hydrochloric acid solution , 5 % sodium hydroxide solution and water . the dried solution was evaporated to give 3 . 04 g of a yellow oil . nmr ( cdcl 3 ): triplet 1 . 37 ppm ( 3h , j = 7 . 0 hz ); quartet 3 . 12 ppm ( 2h , j = 7 . 0 hz ); complex multiplet 7 . 0 - 8 . 0 ppm ( 5h ); doublet 8 . 15 ppm ( 1h , j = 9 . 6 hz ). in a similar manner , the following compounds , as defined in accordance with formula v , were prepared : ______________________________________compound q y m . p . ° c . ______________________________________42 o och . sub . 3 oil43 o och . sub . 2 ch . sub . 3 oil44 o och . sub . 2 ch . sub . 2 ch . sub . 3 oily semi - solid45 o och ( ch . sub . 3 ). sub . 2 oily semi - solid46 o och . sub . 2 ch . sub . 2 ch . sub . 2 ch . sub . 3 oil47 o och . sub . 2 ch ( ch . sub . 3 ). sub . 2 oil48 s och . sub . 3 oil49 s ## str38 ## 137 - 8 ° ______________________________________ s [( propylthio ) thionocarbonyl ] 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzenecarbothioate is a further illustrative compound of this class wherein q is s and y is -- sc 3 h 7 . illustrative compounds of this class are those of the formula : ## str39 ## where r 3 is straight or branched alkyl of 1 to 6 carbons . to a stirred solution of 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl chloride ( 3 . 8 g , 0 . 01 mole ) in ether ( 100 ml ) was added triisopropyl phosphite ( 2 . 1 g , 0 . 01 mole ). the reaction was refluxed for one hour and the disappearance of phosphite monitored by v . p . c .. the ether was stripped off and the resulting oil placed under vacuum ( 1 . 0 mm ) at 40 ° c . for two hours . the resulting amber liquid amounted to 5 . 2 g . nmr ( cdcl 3 ): doublet 1 . 29 ppm ( 3h , j = 6 . 0 hz ); doublet 1 . 37 ppm ( 3h , j = 6 . 0 hz ); multiplet 4 . 88 ppm ( 1h ); complex multiplet 6 . 9 - 8 . 0 ppm ( 5h ); broad doublet 8 . 37 ppm ( 1h , j = 9 . 0 hz ). in a similar manner , the following compound was prepared as an additional example of a benzoyl phosphonate . illustrative compounds of this class are those of the formula : ## str40 ## where a is an alkyl of 1 - 3 carbons or hydrogen . a stirred solution of 3 -[ 2 - chloro - 4 -( trifluromethyl ) phenoxy ] phenyl ethanone ( 15 . 7 g , 0 . 05 mole ) in dichloroethane ( 40 ml ) was cooled to 0 . 5 ° c . nitric acid ( 95 %) ( 4 . 95 g , 0 . 075 mole ) was added , followed by the dropwise addition of 95 % sulfuric acid ( 12 . 3 g , 0 . 125 mole ) while maintaining the temperature below 5 °- 10 ° c . allowed reaction to warm to room temperature . the progress of the reaction was monitored by v . p . c . the reaction solution was poured onto ice water and the organic solution separated , washed with water and dried . the solvent was evaporated to give 16 g of a brown oil , which was extracted with hot heptane . upon cooling , the heptane solution furnished an oil fraction which solidified to give 8 . 8 g of a brown solid , m . p . 58 °- 60 ° c . i . r . ( nujol mull ): c ═ o , 1710 cm - 1 ; no 2 , 1530 and 1315 cm - 1 . 5 -[ 2 - chloro - 4 - trifluoromethyl ) phenoxy ]- 2 - nitrobenzaldehyde (&# 34 ; a &# 34 ; is hydrogen in formula vii ) was prepared . it had a melting point of 99 °- 100 ° c . illustrative compounds of this class include those of the formula : ## str41 ## wherein r 4 is selected from hydrogen and straight or branched chain alkyl of 1 - 4 carbon : r 5 is selected from : phenyl ; ## str42 ## where n is 1 to 5 and x is selected from no 2 , lower alkyl of c 1 - 4 , halogen , phenyl , coor where r is lower alkyl of c 1 - 4 or h or a cation , cn , lower alkyl thio of c 1 - 4 , lower alkoxy of c 1 - 4 , trifluoromethyl and combinations thereof ; heterocyclicalkyl and heterocyclic , heterocyclics of a 5 to 7 member ring comprising carbon in combination with one or more of sulfur , oxygen and nitrogen ; hydroxyl ; alkoxy of 1 - 3 carbons ; -- r 6 co 2 r 6 , where r 6 is an alkyl or alkenyl of up to 3 carbons ; -- r 6 conh 2 ; r 6 con ( r 2 ) 2 ; alkoxyalkyl where the alkoxy and alkyl may each contain a straight or branched c 1 - 3 alkyl chain ; or where r 4 and r 5 together form a heterocyclic ring as hereinabove defined . to a stirred solution of 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl chloride ( 5 . 68 g , 0 . 015 mole ) in toluene ( 35 ml ) was added aniline ( 2 . 8 g , 0 . 30 mole ). the temperature immediately rose to 45 ° c . the reaction was then heated to reflux for twelve hours . the cooled reaction was poured into dilute hydrochloric acid solution . the residual solids were filtered , washed with warm water and dried to give 4 . 1 g of a gray solid m . p . 190 °- 4 ° c . recrystallization from methanol gave 3 . 8 g , m . p . 191 °- 4 ° c . nmr ( d 6 - acetone ): complex multiplet 7 . 0 - 8 . 1 ppm ( 10h ); doublet 8 . 32 ppm ( 1h , j = 9 . 0 hz ); broad singlet 9 . 95 ppm ( 1h ). ______________________________________compound r . sub . 4 r . sub . 5 m . p . ° c ./ oil______________________________________55 h ## str43 ## 145 - 8 56 h ## str44 ## 179 - 81 57 h ## str45 ## 155 - 8 58 h ## str46 ## 169 - 71 59 h ## str47 ## 185 - 7 60 ch ( ch . sub . 3 ). sub . 2 ## str48 ## 144 - 6 61 h ## str49 ## 140 - 1 62 h oh oil 63 h och . sub . 3 171 - 4 64 ch . sub . 3 oh oil 65 ch . sub . 3 och . sub . 3 oil 66 h ch . sub . 2 cooc . sub . 2 h . sub . 5 136 - 7 67 h ## str50 ## oil68 h ## str51 ## 160 - 3 69 h ch . sub . 2 ch . sub . 2 oc . sub . 2 h . sub . 5 86 - 8 70 h ch . sub . 2 ch . sub . 2 ch . sub . 2 och . sub . 3 102 - 4 71 h ## str52 ## 158 - 60______________________________________compound r . sub . 4 and r . sub . 5 m . p . ° c ./ oil______________________________________72 ## str53 ## 107 - 8 73 ## str54 ## 128 - 32 74 ## str55 ## 124 - 6 75 ## str56 ## 169 - 72 76 ## str57 ## oil 77 ## str58 ## 125 - 8______________________________________ ## str59 ## compound name______________________________________ ## str60 ## n [ 2 -( 5 - t - butyl - 1 , 3 , 4 thiadia - zolyl )] 5 -[ 2 - chloro - 4 -( trifl uoro - methyl ) phenoxy ]- 2 - nitro - benzamide ## str61 ## 5 -[ 2 chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl 2 , 5 - dioxopyrolidine ## str62 ## n [ 2 -( 4 , 6 , 6 - trimethyl - 1 , 3 - thiazinyl )] 5 -[ 2 - chloro - 4 -( tri - luoromethyl ) phenoxy ]- 2 - nitro benzamide ## str63 ## n ( carboxymethyl ) 5 -[ 2 - chloro - 4 -( trifluoro - methyl ) phenoxy ]- 2 - nitro benzamide ## str64 ## ncarboxymethyl - nmethyl 5 -[ 2 - chloro - 4 -( tri - fluoromethyl ) p henoxy ]- 2 - nitrobenzamide ## str65 ## n ( 2 , 5 - dichloro - 3 - methoxy - carbonyl ) phenyl 5 -[ 2 - chloro - 4 - trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide ## str66 ## n [ 4 -[ 6 -( 1 , 1 - dimethylethyl )- 3 - methylthio - 1 , 2 , 4 - triazin - 5 ( 4h ) onyl ]] 5 -[ 2 - chloro - 4 -( trifluoro - methyl ) phenoxy ]- 2 - nitrobenzamide ## str67 ## n ( 3 , 4 - dimethyl - 2 , 6 - dinitrophenyl )- n ( 1 - methylethyl ) 5 -[ 2 - chloro - 4 -( tri - fluoromethyl ) phenoxy ]- 2 - nitrobenzami de ## str68 ## n [ 2 , 6 - dinitro - 4 -( tri - fluoromethyl ) phenyl ]- nethyl 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamid e______________________________________ the following 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitro - benzoyl compounds do not readily fall within the defined classes a - g above and are therefore listed below : additional illustrative compounds are listed below according to the structural formula : __________________________________________________________________________ ## str71 ## qa compound name__________________________________________________________________________ ## str72 ## 4 -( 2 , 4 - difluorophenyl )- 2 -( methoxy - carbonyl ) phenyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoa te ## str73 ## 4 -( ethoxycarbonylethyl )- 2 - hydroxy - phenyl 5 -[ 2 chloro - 4 ( tri - fluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str74 ## 3 , 5 - dinitro - 4 - dipropylaminophenyl 5 -[ 2 - chloro - 4 -( trifl uoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str75 ## 2 , 6 - bis ( hydroxymethyl )- 4 - methyl - phenyl 5 -[ 2 - chloro - 4 -( trifluoro - methyl ) phenoxy ]- 2 - nitrobenzo ate ## str76 ## 3 -( 1 , 2 , 5 , 6 - diisopropylidene - d - glucosyl ) 5 -[ 2 - chloro - 4 -( tri - fluoromethyl ) phenoxy ]- 2 - nitro - benzoate ## str77 ## 2 - chloro - 9 -( methoxycarbonyl ) 9hfluoran - 9 - yl 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenyl ]- 2 - nitrobenzoa te ## str78 ## α - benzoyl ( phenylmethyl ) 5 -[ 2 - chloro - 4 -( trifluor omethyl ) phenoxy ]- 2 - nitrobenzoate ## str79 ## 2 -( acetylamino ) ethyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) p henoxy ]- 2 - nitrobenzoate ## str80 ## 2 -( 2 - methylpropanoyl - amino ) ethyl 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str81 ## [ 3 -( dimethylamino )- 2 - methyl propionyloxy ] ethyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str82 ## 2 -( 2 - methylpropenoyloxy )- 2 - methylethyl 5 -[ 2 - chloro - 4 -( tri - fluoromethyl ) phenoxy ]- 2 - nitro - benzoate ## str83 ## ( 1 - cyano - 1 methyl ) ethoxymethyl 5 -[ 2 - chloro - 4 -( trifluor omethyl ) phenoxy ]- 2 - nitrobenzoate ## str84 ## ( ethoxycarbonyl )( acetyl ) methyl 5 -[ 2 - chloro - 4 -( trifluor omethyl ) phenoxy ]- 2 - nitrobenzoate ## str85 ## diethoxyphosphonylmethyl 5 -[ 2 - chloro - 4 -( trifluorometh yl ) phenoxy ]- 2 - nitrobenzoate ## str86 ## dimethoxyphosphonylethyl 5 -[ 2 - chloro - 4 -( trifluorometh yl ) phenoxy ]- nitrobenzoate ## str87 ## dimethoxyphosphonylethoxy ethyl 5 -[ 2 - chloro - 4 -( tri - fluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str88 ## 2 -( chloroacetyl ) ethyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ochf . sub . 2 difluoromethyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str89 ## propenoylaminomethyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) p henoxy ]- 2 - nitrobenzoate ## str90 ## cyano ( ethoxycarbonyl ) methyl 5 -[ 2 - chloro - 4 -( trifluorom ethyl ) phenoxy ]- nitrobenzoate ## str91 ## 4 -( 3 - chlorophenylcarbamoyloxy ) butyn - 2 - yl 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzo ate ## str92 ## n ( chloroacetyl )- n ( 2 , 6 - diethyl - phenylamino ) methyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoa te och . sub . 2 chchcn 3 - cyanopropen - 2 - yl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoatescn 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoic acid anhydride with thiocyanic acid ## str93 ## s ( phenylsulfonylaminoethyl ) 5 -[ 2 - chloro - 4 -( trifluorome thyl ) phenoxy ] 2 - nitrobenzenecarbothioate ## str94 ## s ( 2 , 3 - dihydroxypropyl ) 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzenecarbothioate sch . sub . 2 cooc . sub . 2 h . sub . 5 s ( ethoxycarbonylmethyl ) 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzenecarbothioate sch . sub . 2 cooh s ( carboxymethyl ) 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzenecarbothioate ## str95 ## s [( 3 - fluorophenyl ) methyl ] 5 -[ 2 - chloro - 4 -( trifluorometh yl ) phenoxy ]- 2 - nitrobenzenecarbothioate ## str96 ## s [( ethylthiocarbonyl ) methyl ] 5 -[ 2 - chloro - 4 -( trifluorom ethyl ) phenoxy ]- 2 - nitrobenzene - carbothioate ## str97 ## s [ 2 , 3 - dihydroxypropoxycarbonyl ) methyl ] 5 -[ 2 - chloro - 4 -( trifluoro - methyl ) phenoxy ]- 2 - nitro - benzenecarbothioat e sch . sub . 2 chchcooc . sub . 2 h . sub . 5 s [( 3 - ethoxycarbonyl ) propen - 2 - yl ] 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzene - carbothioate ## str98 ## 1 , 1 dimethyl - 2 , 2 , 2 - trichloro - ethoxycarbonyl 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzo ate ## str99 ## 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoy l oethylphosphonic acid ammonium salt ccl . sub . 3 1 -{ 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrophenyl } 2 , 2 , 2 ,- trichloroethanone cf . sub . 3 1 -{ 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrophenyl } 2 , 2 , 2 ,- trifluoroethanone ## str100 ## dimethyl 5 -[ 2 - chloro - 4 - trifluoro - methyl ) phenoxy ]- 2 - ni trobenzoyl - methylphosphonate ## str101 ## { 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ] 2 - nitrophenyl } 4 - methoxy - 3 - methylphenyl methanone ## str102 ## 1 -{ 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrophe nyl } 2 -( di - methoxyphosphonylmethyl - amino ) ethanone cn 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl cyanide__________________________________________________________________________ ______________________________________miscellaneous - amideqa compound name______________________________________nhch . sub . 2 ch ( och . sub . 3 ). sub . 2 n ( 2 , 2 - dimethoxyethyl ) 5 - [ 2 - chloro - 4 - trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide ## str103 ## n ( carboxymethyl )- n ( phosphonomethyl ) 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide ## str104 ## n ( carboxymethoxy ) 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide ## str105 ## n ( 1 - methylethyl )- n phenylmethyl ) 5 -[ 2 - chloro - 4 - ( trifluorom ethyl ) phenoxy ]- 2 - nitrobenzamide ## str106 ## 3 { 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl } 4 - chloro - 2 - oxobenzothiazoline ## str107 ## n [ 1 , 3 - dihydroxy - 2 - methylpropyl ) 5 -[ 2 - chloro - 4 -( trifluorome thyl ) phenoxy ]- 2 - nitrobenzamide ## str108 ## n ( diethoxyphosphonyl ) 5 -[ 2 - chloro - 4 -( trifluoromethyl ) pheno xy ]- 2 - nitrobenzamide nhch . sub . 2 ch . sub . 2 so . sub . 3 na n ( 2 - sulfoethyl ) 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide sodium salt nhch . sub . 2 so . sub . 3 c . sub . 6 h . sub . 13 n ( 2 - hexyloxysulfonyl ) ethyl 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide ## str109 ## n ( trifluoroacetyl ) 5 -[ 2 - chloro - 4 - ( trifluoromethyl ) phenoxy ] - 2 - nitrobenzamide ## str110 ## n ( 4 - sulfophenyl ) 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide nhc ( ch . sub . 3 ). sub . 2 cn n [( 1 - cyano - 1 - methyl )- 2 - ethyl ] 4 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide ## str111 ## n ( ethoxycarbonyl ) 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide ## str112 ## n [ 2 - methyl - 4 -( phenylsulfonyl ) phenyl ] 5 -[ 2 - chloro - 4 -( triflu oro - methyl ) phenoxy ]- 2 - nitrobenzamide ## str113 ## n ( 4 - aminophenylsulfonyl )- n ( methoxycarbonyl ) 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide nhchnoh n [( hydroxyimino ) methyl ] 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzamide nhnh . sub . 2 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoic acid hydrazide ## str114 ## 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoic acid methyl hydrazide ## str115 ## 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl ( 2 - chloro - acetyl ) hydrazide ## str116 ## 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl 2 -( carbox - amido ) hydrazide nhcn 5 -[ 2 - chloro - 4 -( trifluoromethyl )- phenoxy ]- 2 - nitrobenzoylcyanamide ## str117 ## 5 -[ 2 - chloro - 4 -( trifluoromethyl )- phenoxy ]- 2 - nitrobenzoylcy anamide sodium salt n . sub . 3 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoyl amide onchnh . sub . 2 aminomethyleneamino 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 nitrobenzoate onc ( ch . sub . 3 ). sub . 2 1 - methylethylideneimino 5 -[ 2 - chloro - 4 -( trifluoromethyl ) phenoxy ]- 2 - nitrobenzoate ## str118 ## 1 -( methylthio ) ethylideneamino 5 [ 2 - chloro - 4 -( trifluoromethy l ) phenoxy ]- 2 - nitrobenzoate______________________________________ the compounds of this invention can be applied in various ways to achieve herbicidal action . they can be applied per se , as solids or in vaporized form , but are preferably applied as the toxic components in pesticidal compositions of the compound and a carrier . these compositions are preferably applied directly to the soil and often incorporated therewith . the compositions can be applied as granulars or dusts ; as liquid sprays , or as gas - propelled sprays and can contain , in addition to a carrier , additives such as emulsifying agents , binding agents , gases compressed to the liquid state , odorants , stabilizers , and the like . a wide variety of liquid and solid carriers can be used . non - limiting examples of solid carriers include talc , bentonite , diatomaceous earth , pyrophyllite , fullers earth , gypsum , flours derived from cotton seeds and nut shells , and various natural and synthetic clays having a ph not exceeding about 9 . 5 . non - limiting examples of liquid carriers include water , organic solvents such as alcohols , ketones , light oils , and medium oils and vegetable oils such as cottonseed oil . in practice , herbicidal application is measured in terms of pounds of herbicide applied per acre . the compounds of this invention are effective herbicides when applied in herbicidal amounts , i . e ., at rates between about 0 . 03 pounds and about 10 pounds per acre . crop and weed species are planted in 8 &# 34 ;× 10 &# 34 ; disposable fiber flats containing potting soil to provide each flat with a 4 &# 34 ; row of all test species . crop species consist of field corn ( cn ), crabgrass ( cg ), cotton ( ct ), and soybeans ( sb ). the weed species consist of foxtail millet ( fm ), green foxtail ( cf ), velvetleaf ( vl ), cocklebur ( cb ), wild mustard ( wm ) and pigweed ( fw ). cotton , corn , soybean , and cocklebur plantings consist of 4 to 5 seeds per row depending upon species . the smaller seeded species ( velvetleaf , wild mustard , pigweed , foxtail millet and green foxtail ) are planted in an uncounted but sufficient number to provide a solid row of seedlings . plantings for the pre - and post - emergence portions of the test are identical as to seeding . the initial watering until emergence is done from the top . the post - emergence phase is propagated in advance so as to provide plants of the proper stage of development at the time of treatment . plantings for the pre - emergence phase are made not more than one day in advance of treatment . the desired stage of development for treatment of the post - emergence broadleaf species ( ct , sb , cb , vl , wm , pw ) is the one true leaf or first trifoliate leaf stage . the desired stage for corn would be a height of 3 - 4 &# 34 ;, while a 2 &# 34 ; height would be adequate for the grasses . spray applications are made with a handgun sprayer ( aspirator type ) simultaneously to one flat of established plants for the post - emergence phase and one newly seeded flat for the pre - emergence phase . the 10 lb ./ acre treatment rate consists of the uniform application of 116 milligrams of test compound to the combined area of the two flats ( 160 sq . inches ). application is made in a solvent mixture consisting of 40 ml acetone and 40 ml water and a surfactant concentration of 0 . 1 %. following spray application , flats are returned to the greenhouse where watering of the post - emergence phase is done only by subirrigation . the pre - emergence phase is top watered by sprinkling until after test species have emerged . subsequent watering is by - subirrigation . two weeks after treatment , the pre - and post - emergence injury and control is rated on a 0 - 100 % injury and control scale . special physiological effects are rated as to intensity also at this time . the herbicidal test data reported for compounds 1 - 81 was obtained at application rates of 10 lbs . down to 1 / 4 lb ./ acre . the following lists the metric equivalents for each rate . ______________________________________application rateus - lb ./ acre metric - kg / ha______________________________________10 . 0 11 . 24 . 0 4 . 482 . 0 2 . 241 . 0 1 . 120 . 5 0 . 560 . 25 0 . 28______________________________________ test results are set forth in table i ( pre - emergence ) and table ii ( post - emergence ). table i__________________________________________________________________________ dosagecpd . lbs ./ pre - emergenceno . acre cg fm gf vl cb wm pw ct cn sb__________________________________________________________________________1 10 -- 100 90 90 0 100 100 10 0 0 4 -- 100 90 20 -- 100 -- 0 0 0 2 -- 100 60 10 -- 100 70 0 10 10 1 -- 90 90 30 0 100 100 20 0 10 1 / 2 -- 90 80 0 0 90 100 20 0 10 1 / 4 -- 90 70 30 0 90 80 0 10 02 10 -- 20 20 10 0 70 90 0 0 0 4 -- -- -- -- -- -- -- -- -- -- 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 3 10 -- 90 90 0 0 90 100 0 0 0 4 -- 100 90 30 20 90 100 10 0 0 2 -- 60 10 0 10 30 80 -- 0 0 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 4 10 -- 100 90 90 20 100 100 10 0 10 4 -- 100 90 0 -- 100 -- 0 0 10 2 -- 90 40 0 -- 70 60 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 5 4 -- 90 90 70 30 100 100 60 0 0 2 -- 90 90 10 40 100 100 20 0 10 1 -- 70 10 0 0 70 100 0 0 10 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 6 4 -- 100 90 70 20 100 100 0 40 0 2 -- 100 90 10 0 100 100 40 0 0 1 -- 90 60 0 40 90 90 30 0 0 1 / 2 -- 70 80 10 0 50 90 10 0 10 1 / 4 -- 20 0 10 10 30 0 0 20 107 4 -- 0 0 0 0 100 100 40 0 0 2 -- 70 20 0 0 0 70 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 8 10 -- 0 0 0 0 0 0 0 30 0 4 -- -- -- -- -- -- -- -- -- -- 2 -- -- -- -- -- -- -- -- -- -- 9 4 -- 0 0 0 -- 10 60 10 0 0 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- 10 0 0 0 50 60 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 10 4 -- 10 10 10 0 0 0 10 10 10 2 -- -- -- -- -- -- -- -- -- -- 11 10 -- 0 0 0 0 0 0 0 0 0 4 -- -- -- -- -- -- -- -- -- -- 12 4 -- 100 90 90 60 100 100 40 10 0 2 -- 100 90 40 10 100 100 10 30 0 1 -- 100 90 0 0 100 100 0 0 0 1 / 2 -- 70 30 10 0 90 90 30 0 0 1 / 4 -- 20 20 0 0 20 60 60 60 3013 10 -- 90 90 100 80 100 100 90 10 10 4 -- 90 90 70 10 90 90 10 20 0 2 -- 90 70 30 0 90 90 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 14 4 -- 70 50 10 0 70 60 0 20 0 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 15 4 -- 100 90 40 20 90 90 10 0 0 2 -- 90 90 10 0 90 90 0 0 0 1 -- 70 60 10 0 20 80 20 0 10 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 16 4 -- 90 50 10 0 90 70 10 10 0 2 -- 80 10 10 0 70 0 0 0 10 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 17 4 -- 100 90 40 0 100 100 0 10 0 2 -- 90 90 30 0 90 90 30 0 10 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 18 10 -- 100 80 70 0 100 100 10 0 0 2 -- 100 40 20 10 100 100 10 0 10 1 / 2 -- 90 20 0 10 100 90 10 10 30 1 / 4 -- 10 10 40 10 80 60 10 0 019 10 -- 100 100 80 60 100 100 30 60 0 2 -- 100 70 40 10 100 100 20 10 10 1 / 2 -- 100 60 0 0 100 60 10 0 0 1 / 4 -- 10 10 60 20 70 50 20 0 2020 4 -- 90 80 50 0 100 90 0 0 0 2 -- 80 20 10 20 90 20 0 0 10 1 -- 0 0 0 0 0 20 30 10 10 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 21 4 -- 80 60 20 0 30 20 10 20 20 2 -- -- -- -- -- -- -- -- -- -- 22 4 -- 90 80 20 0 90 90 0 10 0 2 -- 80 70 20 0 80 60 0 20 0 1 -- 90 20 10 20 30 10 40 10 50 1 / 4 -- -- -- -- -- -- -- -- -- -- 23 4 -- 80 0 10 0 90 30 10 0 0 2 -- 70 10 30 0 70 10 0 0 0 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 24 4 -- 90 70 60 10 90 90 0 0 10 2 -- 80 70 40 0 70 80 0 0 0 1 / 2 -- 0 10 0 0 0 10 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 25 4 -- 100 90 90 20 100 100 10 40 10 2 -- 90 90 80 40 100 100 40 10 20 1 -- 100 90 10 0 90 90 0 0 0 1 / 2 -- 90 70 0 0 90 70 10 0 10 1 / 4 -- 10 20 10 0 20 20 0 0 026 2 -- 40 40 20 70 90 70 0 0 10 1 / 2 -- 10 0 10 0 90 40 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 27 2 -- 90 90 80 0 100 100 10 0 0 1 / 2 -- 70 50 40 0 90 100 0 0 0 1 / 4 -- 50 10 0 0 70 10 0 0 028 2 -- 90 90 90 20 100 100 50 10 20 1 / 2 -- 90 90 20 0 100 100 10 0 0 1 / 4 -- 60 20 0 -- 50 80 10 0 029 2 -- 100 100 40 10 100 100 0 0 20 1 / 2 -- 100 90 0 0 100 90 10 0 0 1 / 4 -- 10 40 60 0 90 90 0 0 030 1 / 2 10 60 -- 30 -- 90 90 -- -- -- 1 / 4 10 40 -- 10 -- 10 -- -- -- -- 31 2 -- 60 50 10 0 80 90 30 20 0 1 / 2 -- 10 0 10 0 10 50 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 32 2 -- 90 70 0 0 100 100 10 0 10 1 / 2 -- 90 90 0 0 90 80 0 0 10 1 / 4 -- 30 10 0 0 10 0 0 0 033 2 -- 100 90 50 0 90 90 10 10 40 1 / 2 -- 80 10 0 0 20 10 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 34 2 -- 100 100 10 30 90 90 30 10 0 1 / 2 -- 20 20 20 10 80 20 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 36 2 -- 50 20 40 -- 20 90 10 20 30 1 / 2 -- 0 0 0 -- 20 50 10 10 10 1 / 4 -- -- -- -- -- -- -- -- -- -- 37 2 -- 60 60 0 -- 80 20 0 0 0 1 / 2 -- 0 0 0 -- 0 0 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 38 2 -- 100 90 50 10 100 100 60 0 0 1 / 2 -- 90 50 0 0 50 40 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 39 2 -- 90 90 70 20 100 100 10 20 0 1 / 2 -- 90 70 10 10 100 100 0 0 040 2 -- 100 90 90 0 100 100 10 10 0 1 / 2 -- 90 70 20 0 100 90 10 0 041 2 -- 100 90 40 0 100 90 10 0 0 1 / 2 -- 90 30 0 0 90 70 0 0 0 1 / 4 -- 0 0 0 0 10 10 0 0 042 2 -- 100 100 90 70 100 100 90 20 30 1 / 2 -- 100 100 80 60 100 100 90 20 30 1 / 4 -- 80 90 10 0 60 90 10 0 1043 1 / 2 90 90 -- 50 0 90 100 -- -- -- 1 / 4 60 90 -- 50 -- 10 -- -- -- -- 44 2 -- 100 100 90 30 100 100 60 20 30 1 / 2 -- 90 90 80 10 100 100 20 10 20 1 / 4 -- 20 0 0 0 90 20 0 0 1045 2 -- 100 100 70 10 100 100 10 10 0 1 / 2 -- 90 80 10 0 100 100 0 0 0 1 / 4 -- 90 10 0 0 80 90 0 0 046 2 -- 100 90 20 10 100 90 10 0 0 1 / 2 -- 90 90 10 30 90 70 10 0 0 1 / 4 -- 30 20 0 0 0 0 0 0 047 2 -- 100 90 90 20 100 100 30 10 0 1 / 2 -- 100 90 20 10 100 100 10 0 0 1 / 4 -- 20 0 0 0 90 90 20 10 048 2 -- 100 100 70 100 100 0 0 0 0 1 / 2 -- 100 90 30 0 90 60 40 0 049 2 -- 90 90 60 0 90 100 0 0 0 1 / 2 -- 20 0 10 10 100 90 0 0 1050 2 -- 90 90 90 50 100 100 50 10 30 1 -- 90 90 20 0 100 90 0 0 0 1 / 2 -- 80 70 10 0 100 90 10 10 20 1 / 4 -- 90 70 20 10 90 80 0 0 051 10 -- 100 100 100 50 100 100 10 30 0 4 -- 100 100 90 60 100 100 20 10 20 2 -- 90 90 70 10 100 100 20 0 10 1 -- 100 100 10 0 100 100 0 0 10 1 / 2 -- 90 50 0 10 70 40 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 52 10 100 100 -- 90 -- 100 -- -- -- -- 1 60 70 -- 60 0 90 -- -- -- -- 1 / 2 40 80 -- 50 10 80 -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 53 10 -- 90 90 50 -- 100 100 50 10 0 4 -- 90 90 30 -- 100 100 10 0 0 1 -- 90 60 0 -- 90 90 0 0 0 1 / 2 -- 10 0 10 -- 20 90 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 54 4 -- 0 0 0 0 0 0 0 0 0 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 55 4 -- 0 20 40 10 90 100 60 0 20 2 -- 0 0 0 0 0 0 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 56 4 -- 0 0 30 -- 70 100 30 0 0 2 -- -- -- -- -- -- -- -- -- -- 57 4 -- 10 0 0 -- 70 90 0 0 0 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 58 4 -- 30 0 0 -- 10 100 0 0 0 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- -- 59 10 -- 0 0 0 -- 0 100 0 0 060 10 -- 0 0 10 0 10 70 0 0 0 4 -- -- -- -- -- -- -- -- -- -- 61 2 -- 50 20 60 10 90 80 20 10 20 1 / 2 -- 0 0 0 0 50 0 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 62 4 90 100 -- 80 -- 100 100 -- -- -- 1 90 40 -- 70 -- 100 100 -- -- -- 1 / 2 40 0 -- 10 0 80 -- -- -- -- 63 4 90 90 -- 100 -- 100 100 -- -- -- 1 60 40 -- 70 -- 90 0 -- -- -- 1 / 2 20 0 -- 20 0 10 0 -- -- -- 64 4 90 90 -- 90 -- 100 100 -- -- -- 2 90 90 -- 50 -- 100 90 -- -- -- 1 20 0 -- 40 0 90 0 -- -- -- 1 / 2 0 20 -- 0 0 70 70 -- -- -- 65 4 80 90 -- 90 -- 100 -- -- -- -- 2 -- 30 70 20 0 80 100 0 0 0 1 -- 90 70 80 0 90 90 10 10 0 1 / 2 -- 10 10 50 0 100 100 0 0 0 1 / 4 -- 30 10 10 0 70 80 0 0 066 4 90 90 -- 100 -- 100 100 -- -- -- 1 70 40 -- 70 -- 100 100 -- -- -- 1 / 2 0 10 -- 20 0 60 0 -- -- -- 67 4 90 90 -- 90 -- 100 100 -- -- -- 2 60 70 -- 60 -- 90 90 -- -- -- 1 0 0 -- 10 0 40 0 -- -- -- 1 / 2 0 0 -- 40 10 90 20 -- -- -- 68 10 100 90 -- 100 -- 100 100 -- -- -- 4 -- 100 90 90 60 100 100 0 10 0 2 -- 90 90 90 10 100 100 20 20 20 1 -- 90 30 90 0 100 100 40 0 0 1 / 2 -- 70 80 70 50 100 100 10 0 0 1 / 4 -- 80 60 0 0 100 100 20 0 -- 69 2 -- 100 90 60 50 100 100 10 40 20 1 / 2 -- 100 90 10 10 100 100 0 0 10 1 / 4 -- 0 60 10 10 80 80 10 50 1070 2 -- 100 90 50 50 100 100 10 10 20 1 / 2 -- 100 90 10 30 100 100 20 0 10 1 / 4 -- 0 10 50 0 90 90 0 40 8071 2 -- 90 50 40 0 90 80 10 10 10 1 / 2 -- 10 10 0 0 10 90 10 0 10 1 / 4 -- -- -- -- -- -- -- -- -- -- 72 10 -- 90 90 -- 20 90 90 -- 40 70 2 -- 90 90 70 0 100 100 10 20 0 1 -- 90 80 0 0 90 80 10 0 0 1 / 2 -- 20 0 10 -- 90 90 20 20 10 1 / 4 -- 30 0 10 -- 70 80 0 20 1073 10 -- 100 90 90 30 100 100 20 60 0 4 -- 100 90 80 60 100 90 50 70 10 2 -- 80 70 70 10 100 10 10 0 0 1 -- 90 60 10 0 90 60 20 0 10 1 / 2 -- 90 50 0 0 90 80 0 0 074 2 -- 90 90 70 0 100 100 10 10 0 1 / 2 -- 90 70 0 0 90 50 10 0 0 1 / 4 -- 0 0 10 0 70 70 10 0 1075 2 -- 60 20 0 0 50 80 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 76 2 -- 80 40 80 0 70 70 20 60 10 1 / 2 -- 10 10 0 0 70 70 10 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- 77 2 -- 100 90 10 0 100 90 0 0 0 1 / 2 -- 90 70 0 10 90 60 10 0 078 10 90 90 -- 100 -- 100 -- -- -- -- 4 -- 90 90 90 0 100 100 0 0 0 2 -- 90 90 80 0 90 100 10 0 0 1 -- 40 60 60 10 100 100 0 0 0 1 / 2 -- 50 70 0 -- 90 90 0 0 0 1 / 4 -- 80 50 20 0 90 60 10 30 079 10 70 90 -- 50 -- 90 -- -- -- -- 1 / 4 0 0 -- 0 -- 0 -- -- -- -- 80 4 -- 100 90 40 20 90 90 0 20 10 2 -- 90 80 10 10 90 10 10 10 10 1 -- 10 0 0 0 70 20 0 0 0 1 / 2 -- -- -- -- -- -- -- -- -- -- 1 / 4 -- -- -- -- -- -- -- -- -- -- 81 2 -- 80 50 0 0 90 80 0 0 0 1 / 2 -- 10 0 0 0 10 60 0 0 0 1 / 4 -- -- -- -- -- -- -- -- -- -- __________________________________________________________________________ table ii__________________________________________________________________________ dosagecpd . lbs ./ post - emergenceno . acre cg fm gf vl cb wm pw ct cn sb__________________________________________________________________________1 10 -- 100 100 100 100 100 100 100 80 60 4 -- 90 90 100 100 100 100 90 60 50 2 -- 100 100 100 -- 100 -- 90 50 20 1 -- 100 90 100 -- 100 100 90 30 50 1 / 2 -- 100 90 90 90 100 100 80 70 10 1 / 4 -- 50 50 40 80 100 100 60 50 402 10 -- 90 90 90 80 90 100 90 10 10 4 -- 100 90 90 60 90 90 90 10 10 2 -- 90 90 90 80 100 100 90 20 20 1 -- 90 90 80 90 90 100 90 70 70 1 / 2 -- 80 70 60 90 100 100 90 80 30 1 / 4 -- 90 70 70 80 100 80 90 50 603 10 -- 90 90 90 90 100 100 100 30 30 4 -- 100 100 90 90 100 100 90 30 10 2 -- 100 90 100 90 100 100 90 90 20 1 -- 90 90 90 90 100 100 80 70 60 1 / 2 -- 90 90 90 90 100 90 90 90 60 1 / 4 -- 90 80 90 80 100 100 90 30 104 10 -- 100 100 100 100 100 100 100 90 50 4 -- 100 100 100 -- 100 -- 100 90 30 2 -- 90 90 100 100 100 100 100 20 20 1 -- 100 100 100 -- 100 100 100 40 50 1 / 2 -- 100 90 90 90 100 100 100 70 10 1 / 4 -- 50 70 30 50 90 100 40 30 505 4 -- 100 90 100 100 100 100 90 0 40 2 -- 90 90 100 -- 100 -- 90 10 20 1 -- 90 90 100 0 100 100 90 50 10 1 / 2 -- 80 70 90 80 100 100 90 20 20 1 / 4 -- 60 60 50 70 90 100 60 30 606 4 -- 100 100 100 100 100 100 100 10 60 2 -- 100 100 100 100 100 100 90 80 40 1 -- 70 80 70 70 100 100 60 70 60 1 / 2 -- 90 90 90 90 100 90 80 80 20 1 / 4 -- 80 60 80 50 90 70 90 10 107 4 -- 100 80 100 80 100 100 80 0 20 2 -- 90 30 100 -- 90 100 90 10 20 1 -- 90 70 100 -- 90 100 90 -- 40 1 / 2 -- 90 90 100 -- 90 100 90 10 50 1 / 4 -- 90 90 90 50 100 100 60 30 408 10 -- 90 80 100 60 90 100 40 0 20 4 -- 60 30 -- -- 70 -- 70 20 0 2 -- 80 70 50 -- 70 70 90 0 109 4 -- 90 90 100 40 90 100 90 10 20 2 -- 90 90 90 -- 90 100 90 10 30 1 -- 90 90 100 80 100 100 90 0 10 1 / 2 -- 100 90 90 70 100 100 80 10 10 1 / 4 -- 70 80 30 50 90 100 50 50 4010 4 -- 80 20 70 10 90 50 90 40 10 2 -- 50 50 70 0 90 70 90 70 3011 10 -- 90 90 70 30 80 100 40 0 10 4 -- 30 20 30 20 70 90 80 30 1012 4 -- 90 90 100 90 100 100 90 20 10 2 -- 100 100 90 100 100 100 100 70 40 1 -- 100 100 100 100 100 100 100 60 10 1 / 2 -- 100 100 90 80 100 100 80 80 60 1 / 4 -- 90 90 90 70 100 100 90 60 5013 10 -- 90 90 100 100 100 100 90 80 20 4 -- 100 100 100 100 100 100 100 90 90 2 -- 100 100 90 90 100 100 100 90 50 1 -- 90 90 90 70 100 100 90 70 50 1 / 2 -- 90 90 80 70 100 100 90 70 60 1 / 4 -- 90 80 80 80 100 90 90 60 6014 4 -- 90 90 90 80 100 100 90 30 20 1 -- 90 90 80 10 90 90 90 70 40 1 / 2 -- 90 90 70 70 90 90 80 70 20 1 / 4 -- 80 80 70 50 90 100 80 50 7015 4 -- 90 100 100 90 100 100 100 60 10 2 -- 90 90 90 90 100 90 90 70 30 1 -- 90 90 80 60 90 100 90 50 30 1 / 2 -- 90 90 90 90 100 100 90 50 30 1 / 4 -- 90 70 60 50 70 90 70 50 7016 4 -- 90 90 60 50 100 100 90 50 10 2 -- 30 40 60 30 90 80 70 50 80 1 -- 70 60 70 70 90 90 90 60 70 1 / 2 -- 90 70 70 80 100 100 90 60 40 1 / 4 -- 60 40 60 30 90 100 60 50 5017 4 -- 100 100 100 90 100 100 90 70 30 2 -- 100 100 100 90 100 100 100 80 40 1 -- 90 90 80 60 90 100 70 70 40 1 / 2 -- 90 90 90 90 90 90 90 70 10 1 / 4 -- 80 80 80 50 90 60 90 40 1018 10 -- 100 100 100 90 100 100 90 90 90 2 -- 90 90 100 90 100 100 90 90 80 1 / 2 -- 90 90 100 70 100 100 80 70 60 1 / 4 -- 90 70 90 50 100 100 70 70 5019 10 -- 100 100 100 90 100 100 90 80 40 2 -- 90 90 100 100 100 100 90 60 40 1 / 2 -- 90 90 90 90 100 100 90 80 40 1 / 4 -- 90 70 70 40 100 100 50 60 2020 4 -- 90 90 90 80 100 100 90 40 20 2 -- 70 80 90 70 90 90 90 60 40 1 -- 80 60 70 70 90 80 90 50 20 1 / 2 -- 20 20 60 30 90 90 90 30 30 1 / 4 -- 50 40 40 40 100 50 50 40 5021 4 -- 80 70 90 40 90 90 90 50 20 2 -- 10 20 70 70 80 70 70 30 3022 4 -- 90 90 90 70 90 100 90 80 30 2 -- 80 80 90 20 90 100 90 80 50 1 -- 90 90 70 40 90 -- 60 50 70 1 / 4 -- 50 60 10 10 80 80 50 10 1023 4 -- 90 90 80 60 90 100 90 80 80 2 -- 90 90 90 70 90 -- 90 40 40 1 / 2 -- 20 20 20 10 90 80 80 10 10 1 / 4 -- 70 70 30 20 80 70 80 10 3024 4 -- 100 100 100 90 100 100 90 90 90 2 -- 100 100 100 80 100 -- 90 50 70 1 / 2 -- 60 50 70 20 80 100 90 20 30 1 / 4 -- 70 80 70 50 90 90 90 10 4025 4 -- 100 100 100 100 100 100 100 90 80 2 -- -- -- -- -- -- -- -- -- -- 1 -- 100 100 100 90 100 90 100 90 70 1 / 2 -- 90 90 90 90 100 100 100 90 90 1 / 4 -- 80 80 90 80 90 90 90 40 3026 2 -- 50 70 100 90 100 100 90 30 60 1 / 2 -- 10 0 90 50 90 90 50 20 40 1 / 4 -- 20 10 60 80 90 100 50 10 5027 2 -- 100 100 100 100 100 100 90 70 90 1 / 2 -- 100 100 100 90 100 100 90 60 60 1 / 4 -- 70 60 90 70 100 60 90 50 8028 2 -- 100 90 100 100 100 100 100 90 90 1 / 2 -- 90 90 90 90 100 100 90 90 60 1 / 4 -- 90 90 90 80 100 100 100 70 8029 2 -- 100 100 100 90 100 100 100 60 90 1 / 2 -- 90 90 100 80 100 100 90 10 80 1 / 4 -- 90 90 100 70 100 100 90 50 8030 1 / 2 20 100 -- -- -- 100 100 90 80 60 1 / 4 90 90 -- 70 100 100 100 90 20 4031 2 -- 90 90 100 90 100 100 90 30 60 1 / 2 -- 90 90 100 70 90 100 90 60 30 1 / 4 -- 80 80 100 60 80 100 80 30 7032 2 -- 100 100 100 90 100 100 100 40 80 1 / 2 -- 100 100 100 80 100 100 100 20 80 1 / 4 -- 30 20 100 90 90 90 70 60 4033 2 -- 100 100 100 90 100 100 100 70 80 1 / 2 -- 90 90 100 70 100 100 100 70 80 1 / 4 -- 80 70 90 90 100 100 70 10 4034 2 -- 70 70 100 90 100 100 90 60 60 1 / 2 -- 60 60 100 90 100 100 80 40 40 1 / 4 -- 90 70 90 90 100 100 50 20 5036 2 -- 100 90 90 80 100 100 90 90 50 1 / 2 -- 90 90 90 30 90 100 90 70 60 1 / 4 -- 20 30 90 -- 90 90 90 40 1037 2 -- 90 90 80 0 90 90 90 80 70 1 / 2 -- 90 90 90 -- 90 90 90 40 40 1 / 4 -- 10 10 70 -- 80 70 50 10 3038 2 -- 90 90 100 90 100 100 90 50 60 1 / 2 -- 90 90 100 90 100 100 60 10 50 1 / 4 -- 30 20 90 80 100 100 70 10 1039 2 -- 90 90 100 100 100 100 100 60 90 1 / 2 -- 90 90 90 90 100 100 100 40 7040 2 -- 100 100 100 100 100 100 100 90 90 1 / 2 -- 90 90 100 90 100 100 100 30 7041 2 -- 100 100 100 100 100 100 100 90 90 1 / 2 -- 90 90 100 90 100 90 90 30 80 1 / 4 -- 70 80 90 70 100 90 90 20 6042 2 -- 100 100 100 100 100 100 100 100 90 1 / 2 -- 100 100 90 90 100 100 100 90 90 1 / 4 -- 100 100 100 80 100 100 90 50 8043 1 / 2 70 100 -- 90 100 100 100 100 40 40 1 / 4 100 100 -- 90 100 100 100 70 40 3044 2 -- 100 100 100 100 100 100 100 90 90 1 / 2 -- 100 100 100 90 100 100 90 80 80 1 / 4 -- 90 90 90 70 100 100 90 60 6045 2 -- 100 100 100 100 100 100 100 100 90 1 / 2 -- 100 100 90 90 100 100 100 80 60 1 / 4 -- 100 100 90 90 100 100 90 50 6046 2 -- 100 100 100 90 100 100 100 90 90 1 / 2 -- 100 100 100 70 90 90 100 70 50 1 / 4 -- 90 90 90 30 90 90 90 50 5047 2 -- 100 100 100 100 100 100 100 90 80 1 / 2 -- 90 90 70 90 100 100 90 50 30 1 / 4 -- 90 90 60 20 100 100 80 20 6048 2 -- 100 100 100 90 100 100 100 90 80 1 / 2 -- 90 90 90 90 100 100 100 40 9049 2 -- 50 10 90 70 100 100 60 20 30 1 / 2 -- 10 20 70 30 100 100 90 40 3050 2 -- 90 90 60 90 100 100 90 70 40 1 -- 90 90 100 100 100 100 80 90 60 1 / 2 -- 60 80 90 70 100 100 80 0 10 1 / 4 -- 90 80 90 70 100 100 40 0 3051 10 -- 100 100 100 80 100 100 90 70 70 4 -- 100 100 100 100 100 100 90 90 70 2 -- 90 90 100 90 100 100 90 70 40 1 -- 100 100 100 100 100 100 80 90 80 1 / 2 -- 60 80 100 80 100 100 90 10 20 1 / 4 -- 100 90 100 70 100 90 50 0 4052 10 70 90 -- 100 -- 100 100 80 30 30 1 70 40 -- 100 50 100 100 80 10 40 1 / 2 30 20 -- 70 20 90 100 40 10 10 1 / 4 20 90 -- 30 20 100 100 70 30 1053 10 100 100 -- 100 90 100 100 100 90 90 4 100 90 -- 80 80 100 100 100 70 80 1 90 90 -- 70 60 100 100 90 60 50 1 / 2 40 40 -- 20 0 100 90 80 20 50 1 / 4 20 10 -- 10 -- 90 50 20 10 3054 4 -- 30 30 80 30 100 100 40 10 10 2 -- 20 20 10 -- 90 90 20 10 10 1 -- 80 80 90 40 90 90 50 10 20 1 / 2 -- 60 50 10 -- 90 90 30 10 10 1 / 4 -- 20 40 30 50 80 60 40 40 1055 4 -- 20 20 10 20 100 100 -- 0 10 2 -- 30 30 0 -- 100 80 20 0 80 1 -- 80 80 20 30 90 100 30 20 30 1 / 2 -- 80 80 10 -- 90 -- 80 0 10 1 / 4 -- 20 30 0 30 30 30 0 0 1056 4 -- 80 90 50 70 100 100 20 20 10 2 -- 30 10 30 -- 60 80 70 0 1057 4 -- 60 80 40 30 90 100 70 0 10 2 -- 70 40 0 -- 100 100 60 10 10 1 -- 60 50 0 -- 90 90 60 40 30 1 / 2 -- 20 30 20 -- 90 100 50 10 20 1 / 4 -- 20 20 10 30 60 80 50 10 1058 4 -- 40 70 0 40 90 100 30 -- 20 2 -- 10 10 0 -- 90 100 10 0 10 1 -- 50 50 30 20 70 100 30 20 3059 10 -- 0 10 0 0 0 80 0 0 060 10 -- 80 60 10 70 90 100 30 10 10 4 -- 20 10 10 20 80 70 50 0 1061 2 -- 30 20 90 60 100 100 80 30 30 1 / 2 -- 20 30 80 50 100 100 70 20 30 1 / 4 -- 60 60 90 70 90 100 40 20 3062 4 20 20 -- 0 20 100 -- 30 10 20 1 0 10 -- 10 10 60 70 30 0 30 1 / 2 30 30 -- 0 10 70 50 10 0 2063 4 0 0 -- 0 0 90 -- 20 20 30 1 0 30 -- 20 10 50 80 10 10 20 1 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100 50 90 90 80 20 4071 2 -- 40 60 100 90 100 100 90 20 60 1 / 2 -- 40 40 100 90 100 100 90 10 50 1 / 4 -- 20 10 60 80 90 100 50 10 5072 10 -- 100 100 100 100 100 100 100 90 80 2 -- 100 100 100 90 100 100 100 80 80 1 -- 100 100 100 90 100 100 100 80 80 1 / 2 -- 90 90 90 90 100 100 90 50 80 1 / 4 -- 90 90 90 80 100 100 100 30 8073 10 -- 100 100 100 70 100 100 90 80 50 4 -- 90 90 100 90 100 100 90 70 40 2 -- 30 50 70 40 100 100 50 10 30 1 -- 40 40 50 70 90 100 50 20 30 1 / 2 -- 90 90 80 70 100 100 70 20 2074 2 -- 90 80 90 10 100 100 90 10 40 1 / 2 -- 90 80 90 -- 100 90 90 20 30 1 / 4 -- 60 60 80 90 90 90 90 10 4075 2 -- 80 70 60 20 90 100 90 10 20 1 -- 90 80 80 40 100 70 70 20 20 1 / 2 -- 20 20 50 10 90 90 90 10 10 1 / 4 -- 10 10 70 -- 60 20 50 0 2076 2 -- 20 10 40 -- 90 100 90 10 50 1 / 2 -- 10 10 10 -- 90 90 60 10 40 1 / 4 -- 10 10 80 30 80 70 40 10 1077 2 -- 90 90 100 90 100 100 50 20 30 1 / 2 -- 90 90 90 80 100 100 30 10 3078 10 60 20 -- 70 -- 100 100 90 70 30 4 -- 80 90 100 90 100 100 90 0 10 2 -- 100 100 100 90 100 100 90 50 70 1 -- 90 90 100 60 100 100 40 80 40 1 / 2 -- 90 90 90 80 90 -- 30 20 20 1 / 4 -- 40 80 40 50 80 100 40 40 4079 10 50 60 -- 80 -- 100 100 80 10 20 1 / 2 70 80 -- 40 80 90 100 70 10 1080 4 -- 90 90 100 50 100 90 90 90 30 2 -- 70 50 90 50 90 60 90 60 90 1 -- 70 70 80 20 90 90 90 40 10 1 / 2 -- 30 30 70 50 90 90 90 60 20 1 / 4 -- 50 50 40 50 80 100 50 20 5081 2 -- 40 40 90 70 100 100 90 30 60 1 / 2 -- 30 30 100 50 100 100 90 10 40 1 / 4 -- 40 40 90 30 90 90 50 10 30__________________________________________________________________________ although the present invention has been described with preferred embodiments , it is to be understood that modifications and variations may be resorted to , without departing from the spirit and scope of this invention , as those skilled in the art will readily understand . such modifications and variations are considered to be within the purview and scope of the appended claims .