Abstract:
The present invention relates to novel benzenesulfonylurea derivatives, having a herbicidal activity, which is described in the following structure of general formula (I) ##STR1## wherein R 1  is H,C 1  -C 3  alkyl, C 1  -C 3  haloalkyl, halogen, CN, NO 2 , C 1  -C 3  alkoxy, C 1  -C 3  haloalkoxy, SO 2  NR I  R II , C 1  -C 3  alkylthio, C 1  -C 3  alkylsulfinyl, C 1  -C 3  alkylsulfonyl, SCH 2  F, NH 2 , NHCH 3 , N(Me) 2 , C 1  -C 2  alkyl substituted with C 1  -C 2  alkoxy, C 1  -C 2  haloalkoxy, SH, SCH 3 , CN or OH, or CO 2  R III  ; and then R 1  is H, C 1  -C 4  alkyl, C 2  -C 3  cyanoalkyl, methoxy or ethoxy; R II  is H, C 1  -C 4  alkyl, C 3  -C 4  alkenyl, or when taken together connecting R I  and R II , --(CH 2 ) 3  --, --(CH 2 ) 4  --, --(CH 2 ) 5  -- or --CH 2  CH 2  OCH 2  CH 2  -- , may be formed; 
     R III  is C 1  -C 4  alkyl, C 3  -C 4  alkenyl, C 3  -C 4  alkynyl, C 1  -C 4  alkyl substituted with 1˜3 halogens or cyano grour)s, C 5  -C 6 , cycloalkyl, C 3  -C 7  cycloalkylalkyl or C 2  -C 4  alkoxyalkyl; 
     R 2  is C 1  -C 6 , alkyl substituted with 1˜3 halogens; 
     R 3  is H or CH 3  ; 
     W is O or S; 
     A is a heterocyclic ring defined in the specification; and these may be an agriculturally suitable salt.

Description:
This is a 371 of PCT/KR92/00007, filed Mar. 9, 1992. 
     TECHNICAL FIELD 
     The present invention relates to novel benzenesulfonylurea derivatives having agriculturally suitable for herbicidal activity. 
     BACKGROUND OF THE INVENTION 
     It is publicly well known that sulfonyl urea derivatives have a herbicidal activity. Here are the formulas for the sulfonyl ureas. 
     1) U.S. Pat. No. 4,332,611 discloses the compound having the following formula ##STR2## wherein, L is OH, ##STR3## R is H, F, Cl, Br, NO 2 , CF 3  or C 1  -C 3  alkyl or alkoxy; R 1  is H or C 1  -C 4  alkyl; 
     R 2  is H or CH 3  ; 
     R 8  is H, CH 3  or OCH 3  ; 
     R 11  is H, C 1  -C 5  alkenyl or C 2  -C 3  alkynyl; 
     A is pyrimidine or triazine. 
     2) U.S. Pat. No. 4,786,314 discloses the compound having the following formula ##STR4## wherein R 1  is F, Cl, Br, NO 2 , C 1  -C 4  alkyl, C 2  -C 4  alkenyl, C 2  -C 4  haloalkenyl, C 2  -C 4  alkynyl, C 1  -C 4  haloalkyl, C 1  -C 4  alkoxy or C 1  -C 2  alkyl substituted with OH, alkoxy, alkylthio, phenyl or CH 2  CN; 
     R 2  is ##STR5## etc (R 16  is alkyl); X is alkyl, alkoxy, etc. 
     Y is alkyl, alkoxy, halogen, etc. 
     3) U.S. Pat. No. 4,838,926 discloses the compound having the following formula ##STR6## wherein Q is C 1  -C 4  alkyl substituted with R 2  ; 
     R 2  is OR 3 , ##STR7## etc.; R 3  is H, C 1  -C 4  alkyl, alkenyl, alkynyl or haloalkyl etc.; 
     L is ##STR8## etc.; R 12  is H or CH 2 . 
     4) European Patent No. 125,205 discloses the compound having the following formula ##STR9## wherein R 6  is H, alkyl or F; 
     R 7  is H or CH 3  ; 
     X 1  is O or S; 
     R 8  is haloalkyl or alkoxyalkyl. 
     5) U.S. Pat. No. 4,348,220 discloses the compound having the following formula ##STR10## wherein, L is OR 9  ; 
     R 1  is H or C 1  -C 4  alkyl; 
     R 2  is H or CH 3  ; 
     R 9  is C 1  -C 6  alkyl, C 3  -C 4  alkenyl or C 5  -C 6  cycloalky. 
     As the above patents, many sulfonyl urea herbicides have known until recently. 
     Even with these herbicides, more and more weeds develop immunity forwards these herbicides and cause undesirable vegetations. Thus, continuous research is in demand to develop more effective and newer for a good harvest. 
     Therefore, the object of the presentation is to invent a new benzenesulfonylurea derivative having a very prominent herbicidal activity with a good selectivity for various vegetations and agriculturally suitable herbicides for treatment for pre-emergence and/or post-emergence or plant growth regulants. 
     SUMMARY OF THE INVENTION 
     The present invention relates to novel benzenesulfonylurea derivatives having the following general formula (I) ##STR11## wherein, R 1  is H, C 1l  -C 4  alkyl, C 1  -C 3  haloalkyl, halogen, CN, NO 2 , C 1  -C 3  alkoxy, C 1  -C 3  haloalkoxy, SO 3  NR I  R II , C 1  -C 3  alkylthio, C 1  -C 3  alkylsulfinyl, C 1  -C 3  alkylsulfonyl, SCH 3  F, NH 2 , NHCH 3 , N(ME) 2 , C 1  -C 2  alkyl substituted with C 1  -C 2  alkoxy, C 1  -C 2  haloalkoxy, SH, SCH 3 , CN or OH, or CO 2  R III  ; and then R 1  is H, C 1  -C 4  alkyl, C 2  -C 3  cyanoalkyl, methoxy or ethoxy; R II  is H, C 1  -C 4  alkyl, C 3  -C 4  alkenyl, or when taken together connecting R I  and R II , --(CH 2 ) 3  --, --(CH 2 ) 4  --, --(CH 2 ) 5  -- or CH 2  CH 2  OCH 2  CH 2  --, may be formed; 
     R III  is C 1  -C 4  alkyl, C 3  -C 4  alkenyl, C 3  -C 4  alkynyl, C 1  -C 4  alkyl substituted with 1˜3 halogens or cyano groups, C 5  -C 6  cycloalkyl, C 4  -C 7  cycloalkylalkyl or C 2  -C 4  alkoxyalkyl; 
     R 2  is C 1  -C 6  alkyl substituted with 1˜3 halogens; 
     R 3  is H or CH 3  ; 
     W is O or S; 
     A is A1, A2, A3, A4, A5, A6 or A7 as followings: ##STR12## wherein, X is H, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 1  -C 4  haloalkoxy, C 1  -C 4  haloalkyl, C 1  -C 4  haloalkylthio, C 1  -C 4  alkylthio, halogen, C 2  -C 5  alkoxyalkyl, C 2  -C 5  alkoxyalkoxy, amino, C 1  -C 3  alkylamino, di(C 1  -C 3  alkyl) amino or C 3  -C 5  cycloalkyl; 
     Y is H, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 1  -C 4  haloalkoxy, C 1  -C 4  haloalkylthio, C 1  -C 4  alkylthio, C 2  -C 5  alkoxyalkyl, C 2  -C 5  alkoxyalkoxy, amino, C 1  -C 3  alkylamino, di(C 1  -C 3  alkyl)amino, C 3  -C 4  alkyloxy, C 3  -C 4  alkynyloxy, C 2  -C 5  alkylthioalkyl, C 1  -C 4  haloalkyl, C 2  -C 4  alkynyl, azido, cyano, C 2  -C 5  alkylsulfinylalkyl, C 2  -C 5  alkylsulfonylalkyl, CH 2  OH, C 3  -C 5  cycloalkyl, C 3  -C 5  cycloalkoxy, ##STR13## m is 2 or 3; 
     L 1  and L 2  are independently O or S; 
     R 4  and R 5  are independently C 1  -C 2  alkyl; 
     R 6  is H, or CH 3  ; 
     Z is CH, N, CCH 3  or CC 2  H 5  ; 
     Y 1  is O or CH 2  ; 
     X 1  is CH 3 , OCH 3 , OC 2  H 5  or OCHF 2  ; 
     Y 2  is CH 3 , CH 2  CH 3 , OCH 3 , OCH 2  CH 3 , SCH 3  or SCH 2  CH 3  ; 
     X 2  is CH 3 , CH 2  CH 3 , or CH 2  CF 3  ; 
     Y 3  is H or CH 3  ; 
     X 3  is CH 3  or OCH 3  ; 
     Y 4  is CH 3 , OCH 3 , OC 2  H 5 , CH 2  OCH 3  or Cl; 
     X 4  is CH 3 , OCH 3 , OC 2  H 5 , CH 2  OCH 3  or Cl; 
     and these may be an agriculturally suitable salt, and then, 
     (1) if X is Cl, Br, F or I, Z is CH and Y is OCH 3 , OC 2  H 5 , NCH 3  (OCH 3 ), NH 2 , NHCH 3 , N(CH 3 ) 2  or OCHF 2  ; 
     (2) if X or Y is OCHF 2 , Z is CH; 
     (3) X 4  and Y 4  are not Cl simultaneously; 
     (4) if W is S, R 3  is H, A is A 1 , Z is CH or N and, Y is CH 3 , OCH 3 , OCH 2  CH 3 , CH 2  OCH 3 , C 2  H 5 , CF 3 , SCH 3 , OCH 2  CH═CH 2 , OCH 2  C═CH, OCH 2  CH 2  OCH 3 , CH(OCH 3 ) 2  or ##STR14## (5) if a number of total carbon atoms of X and Y is more than 4, a number of carbon atoms of R 2  is 4 or less than 4. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     Among the definitions according to the present invention, the following terms have the following meanings; 
     a) &#34;Alkyl&#34; used ether alone or in compound word such as &#34;alkylthio&#34; or &#34;haloalkyl&#34; etc. denotes straight chain or branched alkyls such as methyl, ethyl, n-propyl, isopropyl or butyl isomers. 
     b) &#34;Alkoxy&#34; denotes methoxy, ethoxy, n-propoxy, isopropoxy or butoxy isomers. 
     c) &#34;Alkenyl&#34; denotes straight chain or branched alkenes, for example, vinyl, 1-propenyl, 2-propenyl, or butenyl, pentenyl, hexenyl or heptenyl isomers etc. 
     d) &#34;Alkynyl&#34; denotes straight chain or branched alkynyl such as ethynyl, 1-propynyl, 2-propynyl, or butynyl, pentynyl or hexynyl isomers. 
     e) &#34;Halogen&#34; used ether alone or in compound word &#34;halo&#34; denotes chlorine, fluorine, bromine or Iodine. 
     A preferred group of benzene sulfonyl urea derivatives having the formula(I) shown as the below, in view of easiness of synthesis and herbicidal activity, wherein 
     (1) R 3  is H, W is O; 
     (2) R 1  is H, F, Cl, C 1  -C 2  alkyl, C 1  -C 2  haloalkyl, C 1  -C 2  alkoxy, C 1  -C 2  haloalkoxy, C 1  -C 2  alkylthio, CH 2  OCH 3  or CH 2  SCH 3  ; 
     (3) X is CH 3 , OCH 3 , OCH 2  CH 3  Cl, F, Br, OCHF 2 , CH 2  F, OCH 2  CH 2  F, OCH 2  CHF 2 , OCH 2  CF 3 , CF 3 , CH 2  Cl or CH 2  Br; 
     Y is H, C 1  -C 3  alkyl, OCH 3 , OCH 2  CH 3 , CH 2  OCH 3 , NHCH 3 , NCH 3  (OCH 3 ), N(CH 3 ) 2 , CF 3 , SCH 3 , OCH 2  CH═CH 2 , OCH 2  C.tbd.CH, CH 2  OC 2  H 5 , OCH 2  CH 2  OCH 3 , CH 2  SCH 3 , OCHF 2 , SCHF 2  cyclopropyl, C.tbd.CH, or C.tbd.C--CH 3  ; 
     (4) R 2  is CH 2  F, CHF 2 , CHFCl, CH 2  CL, CH 2  Br, CHFCH 3 , CH 2  CH 2  F, CH 2  CH 2  Cl, CHClCH 3 , CHCl 2 , CHFCH 2  F, CHClCH 2  Cl, CHFCH 2  Cl or CH 2  CF 3  ; 
     (5) A is A 1 , and Z is CH; 
     X is CH 3 , OCH 3 , OCH 2  CH 3 , Cl or OCHF 2  ; 
     Y is CH 3 , C 2  H 5 , OCH 3 , CH 2  OCH 3 , CH(OCH 3 ) 2 , OCHF 2 , NHCH 3 , N(Me) 2  or cyclopropyl, and R 1  is H, CH 3 , OCH 3  or Cl. 
     A Special group of benzenesulfonylurea derivatives having the formula(I) shown as following compounds, in view of easiness of synthesis and herbicidal activity; 
     N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-hydroxyethyl)benzenesulfonamide, 
     2-(2-fluoro-1-hydroxyethyl)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, 
     2-(2-chloro-1-hydroxyethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, 
     N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-hydroxy-n-propyl)benzenesulfonamide, 
     2-(2-chloro-1-hydroxy-n-propyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, 
     2-(2,2-difluoro-1-hydroxyethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, etc. 
     In the above compounds, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-hydroxy-n-propyl)benzenesulfonamide existing to two diastereometric isomers, has stronger herbicidal activity in paddy field, when the compound has low m.p. (166°˜168° C.) in comparison with the compound of high m.p. (189°˜191° C.). 
     The novel compounds having the above formula(I) according to the present invention have a very strong herbicidal activity and a good selectivity for a useful vegetation. 
     The compounds of the present invention can be prepared by reactions as described in herein below. 
     The compounds of general formula(I) can be obtained by hydrolyzing the compounds of following formula(II) with alkali under water, organic solvent or the mixture solution thereof. ##STR15## 
     In the above reaction scheme of Method 1, Ac is acetyl group, but it may be a protecting group easily dissolved by acid, alkali or others. In order to hydrolyze the above Ac group, alkali base such as NaOH, KOH, LiOH, Na 2  CO 3 , K 2  CO 3 , etc., preferably LiOH, may be used. 
     The above reaction of Method I is carried out under water or organic solvent, and also a mixture of water with unreacting solvent such as methanol, ethanol, acetone or THF etc., or solvent alone. 
     The hydrolysis in the reaction occurs at the temperatures of 0°˜80° C. and the reaction time of 1˜24 hours, and then the obtained product may be easily separated by acidifying with HCl water solution. 
     As an other process, after acidifying, the obtained product is extracted with methylene chloride, ethyl acetate, etc. then concentrated/crystalized to obtain the final product. If necessary, a pure product can be obtained by purification to column chromatograph. 
     The compounds of the above formula(I) according to the present invention can be prepared by reacting the compounds having the following formula(II) with alkali at the temperature of 25°˜40° C. (Method 2) ##STR16## 
     The reaction of process Method 2 may be preferably carried out under alkali such as NaOH etc. of a small quantity. The product may be separated as the same with the above Method I. 
     On the other hand, the compound of the above formula(II) used in the present invention can be prepared by reacting the compound of following formula(IV) with formula(V). ##STR17## 
     The above reaction may be carried out in solvent such as dioxane, aceonitrile, THF, acetone, MC, toluene or butanone, and then the solvent can be used with small amount of strong base such as Dabco(1,4-diazabicyclo[2.2.2]octane), DBU(1,8-diazabicyclo[5.4.0]undece-7-ene), etc., while reacting at temperature of 20°˜80° C. 
     This reaction is disclosed on U.S. Pat. No. 4,443,245, and thereafter the final product may be obtained by treatment with acid as the method disclosed on European Patent No. 44,870. 
     The above compound of formula(III) may be synthesized by the method disclosed on U.S. Pat. No. 4,370,480. 
     The compounds of general formula(I) can be obtained by reaction the compound of above formula(IV) protected by t-butyldimethylsilane with phenyl carbamate of the above formula(V). ##STR18## 
     The above reaction may be carried out by adding tetrabutylammonium fluoride in the mixture of carbamate and sulfonamide to obtain the desired product. 
     In order to prepare carbamate of the above formula(V), amine of below formula(VI) is reacted with diphenylcarbonate or phenylchloroformate under the presence of base as following reaction process. ##STR19## 
     On the other hand, the compound of the above formula(IV) can be prepared by the following reaction process. ##STR20## 
     In the above reaction, 2 equivalents of n-butyl lithium is added in t-butylsulfonamide under THF solution at the temperature of -80°˜+50° C. for 1˜24 hrs to obtain dilithio salt, and thereafter ##STR21## is added while maintaining the temperature of -70°˜-80° C. to produce ketone compound. In the above, L is alkoxy, N(CH 3 ) 2 , NCH 3  (OCH 3 ), etc. 
     A method for directly lithiating arylsulfonamide is disclosed on J. G. Lombardino, J. Org. Chem., 36, 1843(1971), and also stowell, J. C. &#34;Carbanions in Org. Synthesis&#34;, John Wiley &amp; Sons; New York, 1979; Snieckus, V. Tetrahedron Lett. 26, 1145(1985) and ibid, 1149(1985). 
     It is well known reactions which the lithiated carban ions get up acylation, and hydroxy compound is obtained by reducing ketone with LiAlH 4  or NaBH 4 . 
     A reaction of O-acylation is carried out by reacting the obtained hydroxy compound with acetic anhydride under the presence of pyridine, and easily by use of DMAP as a catalyst. The obtained N-t-butyl-sulfonamide is reacted with trifluoroacetic acid, and then t-butyl group is separated to obtain primary sulfonamide of formula(IV). 
     This process may be easily carried out by a skill person in field of organic compounding technology in accordance with the method disclosed on J. D. Catt and W. L. Matier, J. Org. Chem., 39, 566(1974), ibid 38, 1974(1973), or in the case of treatment of polyphosphoric acid, J. G. Lombardino, J. Org. Chem., 36, 1843(1971). Then, an excess amount (about 0.3M) of trifluoro acetic acide is used, and the reacting solution is stirred at the temperature of 0°˜50° C. for 1˜72 hrs. 
     The volatile material of the obtained product is evaporated under vacuum, and then the residue is crystalized in solvent such as diethylether, ethylacetate, etc. In the above reaction process, R1 is a functional group which is stable for high reactive reagent. 
     The heterocyclic amine compound of formula (VI) may be prepared by a skill person in this technical field from a method disclosed in literatures or the simple transformation of it. 
     For example, European Patent Application No. 84,244 (Pub. Jul. 27, 1983) and J. Am. Chem. Soc., 69,3072 (1947) of W. Braker et al. discloses a method for preparing aminopyrimidine and triazine substituted with acetyl group. European Patent No. 72,347 and U.S. Pat. No. 4,443,243/4,487,915 disclose a method for preparing aminopyrimidine and/or triazine substituted with haloalkyl such as OCHF 2 , SCHF 2 , OCH 2  CH 2  F and OCH 2  CF 3  etc. and haloalkylthio as a substitution group. 
     European Patent No. 108,708, U.S. Pat. No. 4,515,626/4,600,428 disclose cyclopropylpyrimidine and/or triazine substituted with alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino and alkoxyalkyl group etc. 
     European Patent No. 15,863 discloses a method for preparing the compound of the above formula(VI), as 5,6-dihydro-puro[2,3-d]pyrimidine-2-amine compounds and cyclopenta[d]pyrimidine-2-amine compounds which A is A 2  ; and 6,7-dihydro-5H-pyrano-[2,3-d]pyrimidine-2-amine compound with A is A 3 . 
     European Patent No. 46,677 discloses puro[2,3-d]pyridine-2-amine compounds which A is A 4  in the formula(VI), and European Patent No. 73,562 discloses heterocyclic compounds which A is A 5 . 
     The compound of formula(VI) which A is A 6  can be prepared by European Patent No. 94,260. The compound of formula(VI) which A is A 7  can be manufactured by the method of European Patent No. 125,864. 
     Common methods for preparing aminopyridine and triazine compounds are arranged on the following literatures: &#34;The chemistry and Heterocyclic compounds&#34;, Series, Interscience Publishers, Inc., New York and London; &#34;Pyrimidines&#34;, Vol. 16, D. J. Brown Ed.; &#34;S-Triazines and Derivatives&#34;, Vol. 13, E. M. Smolin and L. Rapaport. Compositions of triazine compounds is disclosed in F. C. Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812(1963). 
     On the other hand, salts of the compound of the above formula(I) also are useful as herbicide, and they can be prepared by various methods according to prior art. 
     For example, metal salts of the compound can be prepared by reacting the above formula(I) compounds with strong basic anion, e.g. alkali or alkaline earth metal solution having hydroxyl group, alkoxide or carbonate, and also quaternary amine salt alike. 
     A salt of the formula(I) compound may also be obtained by cation exchange. The cation exchange can be manufactured by directly reacting solution containing cation for exchange with solution of salt of formula(I), for example, solution of alkali metal or quaternary amine salt. 
     This method is useful when the desired salt is water insoluble, for example, copper salt is separarated by filtering. 
     This ion exchange may be carried out by passing through a column of cation exchange resin with solution of salt of the formula(I), for example, alkaline metal or quartermary amine salt solution. 
     This method is useful when the desirable salt is water soluble, especially sodium, potassium or calcium salt. 
     The above manufacturing methods are summarized briefly, but the methods can be easily carried out by a skill person in this technical field of composition and manufacturing for sulfonyl urea or organic composition. 
     The compounds of the above general formula(I) according to the present invention are specified as the following Tables 1˜9; 
     
                                           TABLE 1__________________________________________________________________________ ##STR22##R.sup.1 R.sup.2 R.sup.3            X       Y              mp (°C.)__________________________________________________________________________H     CH.sub.2 F         H  OCH.sub.3                    OCH.sub.3      180-181H     CH.sub.2 F         H  CH.sub.3                    OCH.sub.3      153-155H     CH.sub.2 F         H  CH.sub.3                    CH.sub.3       148-150H     CH.sub.2 F         H  Cl      OCH.sub.3H     CH.sub.2 F         H  Br      OCH.sub.3H     CH.sub.2 F         H  H       CH.sub.3H     CH.sub.2 F         H  OCH.sub.3                    HH     CH.sub.2 F         H  OCH.sub.3                    CH.sub.2 OC.sub.2 H.sub.5H     CH.sub.2 F         H  OCF.sub.2 H                    OCH.sub.3H     CH.sub.2 F         H  OCH.sub.3                    CH(OCH.sub.3).sub.2H     CH.sub.2 F         H  CH.sub. 3                    OC.sub.2 H.sub.5H     CH.sub.2 F         H  CH.sub.3                    CH.sub.2 OCH.sub.3H     CH.sub.2 F         H  OCH.sub.3                    CH.sub.2 OCH.sub.3H     CH.sub.2 F         H  C.sub.2 H.sub.5                    OCH.sub.3H     CH.sub.2 F         H  OC.sub.2 H.sub.5                    OCH.sub.3H     CH.sub.2 F         H  OCH.sub.2 CF.sub.3                    OCH.sub.3H     CH.sub.2 F         H  CF.sub.3                    OCH.sub.3H     CH.sub.2 F         H  CH.sub.2 F                    OCH.sub.3H     CH.sub.2 F         H  CH.sub.2 Cl                    OCH.sub.3H     CH.sub.2 F         H  CH.sub.2 Br                    OCH.sub.3H     CH.sub.2 F         H  F       OCH.sub.3H     CH.sub.2 F         H  I       OCH.sub.3H     CH.sub.2 F         H  OCH.sub.2 CH.sub.2 F                    OCH.sub.3H     CH.sub.2 F         H  OCH.sub.2 CH.sub.2 CF.sub.3                    OCH.sub.3H     CH.sub.2 F         H  OCH.sub.2 CHF.sub.2                    CH.sub.3H     CH.sub.2 F         H  OCH.sub.2 CF.sub.3                    CH.sub.3H     CH.sub.2 F         H  Cl      OC.sub.2 H.sub.5H     CH.sub.2 F         H  OC.sub.2 H.sub.5                    NHCH.sub.3H     CH.sub.2 F         H  OC.sub.2 H.sub.5                    CH.sub.2 SCH.sub.3H     CH.sub.2 F         H  OCF.sub.2 H                    CH.sub.3H     CH.sub.2 F         H  Cl      OCF.sub.2 HH     CH.sub.2 F         H  NH.sub.2                    OC.sub.2 H.sub.5H     CH.sub.2 F         H  n-C.sub.3 H.sub.7                    OCH.sub.3H     CH.sub.2 F         H  NHCH.sub.3                    OCH.sub.3H     CH.sub.2 F         H  OCH.sub.3                    SCH.sub.3H     CH.sub.2 F         H  OCH.sub.3                    SCF.sub.2 HH     CH.sub.2 F         H  OCH.sub.3                    OCH.sub.2 CCHH     CH.sub.2 F         H  OCH.sub.3                    OCH.sub.2 CHCH.sub.2H     CH.sub.2 F         H  OCH.sub.3                    CCHH     CH.sub.2 F         H  OCH.sub.3                    N(CH.sub.3).sub.2H     CH.sub.2 F         H  OCH.sub.3                    cyclopropylH     CH.sub.2 F         H  OCH.sub.3                    NH.sub.2H     CH.sub.2 F         H  OCH.sub.3                    CF.sub.3H     CH.sub.2 F         H  OCH.sub.3                    OCH.sub.2 CH.sub.2 OCH.sub.3H     CH.sub.2 F         H  OCH.sub.3                    CH.sub.2 SCH.sub.3H     CH.sub.2 F         H  OCH.sub.3                    CHOH     CH.sub.2 F         H  OCH.sub.3                    COCH.sub.3H     CH.sub.2 F         H  OCH.sub.3                    CH(SCH.sub.3)OC.sub.2 H.sub.5H     CH.sub.2 F         H  OCH.sub.3                    C(CH.sub.3)(SCH.sub.3).sub.2H     CH.sub.2 F         H  OCH.sub.3                    C(SC.sub.2 H.sub.5).sub.2H     CH.sub.2 F         H  OCH.sub.3                    1,3-dioxolan-2-ylH     CH.sub.2 F         H  OCH.sub.3                    2-methyl-1,3-oxathiolan-2ylH     CH.sub.2 F         H  OCH.sub.3                    1,3-oxathian-2-ylH     CH.sub.2 F         H  OCH.sub.3                    2-methyl-1,3-dithian-2-ylH     CH.sub.2 F         H  OCH.sub.3                    4-methyl-1,3-dioxolan-2-ylH     CH.sub.2 F         H  OCH.sub.3                    2-4-dimethyl-1,3-dithiolan-2-ylH     CH.sub.2 F         H  OCH.sub.3                    N(OCH.sub.3)(CH.sub.3)H     CH.sub.2 F         H  OCH.sub.3                    CCCH.sub.3H     CH.sub.2 F         H  OCH.sub.3                    C.sub.2 H.sub.5H     CH.sub.2 F         H  OCH.sub.3                    OCF.sub.2 BrH     CHFCH.sub.3         H  OCH.sub.3                    OCH.sub.3      189-191 (high mp)H     CHFCH.sub.3         H  OCH.sub.3                    OCH.sub.3      166-168 (low mp)H     CHFCH.sub.3         H  CH.sub.3                    OCH.sub.3      147-149H     CHFCH.sub.3         H  CH.sub.3                    CH.sub.3H     CHFCH.sub.3         H  Cl      OCH.sub.3H     CHFCH.sub.3         H  Br      OCH.sub.3H     CHFCH.sub.3         H  CH.sub.3                    HH     CHFCH.sub.3         H  OCH.sub. 3                    HH     CHFCH.sub.3         H  OCH.sub.3                    CH.sub.2 OC.sub.2 H.sub.5H     CHFCH.sub.3         H  OCF.sub.2 H                    OCH.sub.3H     CHFCH.sub.3         H  OCH.sub.3                    CH(OCH.sub.3).sub.2H     CHFCH.sub.3         H  CH.sub.3                    OC.sub.2 H.sub.5H     CHFCH.sub.3         H  CH.sub.3                    CH.sub.2 OCH.sub.3H     CHFCH.sub.3         H  OCH.sub.3                    CH.sub.2 OCH.sub.3H     CHFCH.sub.3         H  OCH.sub.3                    C.sub.2 H.sub.5H     CHFCH.sub.3         H  OC.sub.2 H.sub.5                    OCH.sub.3H     CHFCH.sub.3         H  OCH.sub.2 CF.sub.3                    OCH.sub.3H     CHFCH.sub.3         H  CF.sub.3                    OCH.sub.3H     CHFCH.sub.3         H  CH.sub.2 F                    OCH.sub.3H     CHFCH.sub.3         H  CH.sub.2 Cl                    OCH.sub.3H     CHFCH.sub.3         H  CH.sub.2 Br                    OCH.sub.3H     CHFCH.sub.3         H  F       OCH.sub.3H     CHFCH.sub.3         H  I       OCH.sub.3H     CHFCH.sub.3         H  OCH.sub.2 CH.sub.2 F                    OCH.sub.3H     CHFCH.sub.3         H  OCH.sub.2 CH.sub.2 CF.sub.3                    OCH.sub.3H     CHFCH.sub.3         H  OCH.sub.2 CHF.sub.2                    CH.sub.3H     CHFCH.sub.3         H  OCH.sub.2 CF.sub.3                    CH.sub.3H     CHFCH.sub.3         H  Cl      OC.sub.2 H.sub.5H     CHFCH.sub.3         H  OC.sub.2 H.sub.5                    NHCH.sub.3H     CHFCH.sub.3         H  OCH.sub.3                    CH.sub.2 SCH.sub.3H     CHFCH.sub.3         H  OCF.sub.2 H                    CH.sub.3H     CHFCH.sub.3         H  Cl      OCF.sub.2 HH     CH.sub.2 CH.sub.2 F         H  OCH.sub.3                    OCH.sub.3      125-127H     CH.sub.2 CH.sub.2 F         H  CH.sub.3                    OCH.sub.3      132-134H     CH.sub.2 CH.sub.2 F         H  CH.sub.3                    CH.sub.3H     CH.sub.2 CH.sub.2 F         H  Cl      OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  Br      OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  CH.sub.3                    HH     CH.sub.2 CH.sub.2 F         H  OCH.sub.3                    HH     CH.sub.2 CH.sub.2 F         H  OCH.sub.3                    CH.sub.2 OC.sub.2 H.sub.5H     CH.sub.2 CH.sub.2 F         H  OCF.sub.2 H                    OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCH.sub.3                    CH(OCH.sub.3).sub.2H     CH.sub.2 CH.sub.2 F         H  CH.sub.3                    OC.sub.2 H.sub.5H     CH.sub.2 CH.sub.2 F         H  CH.sub.3                    CH.sub.2 OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCH.sub.3                    CH.sub.2 OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCH.sub.3                    C.sub.2 H.sub.5H     CH.sub.2 CH.sub.2 F         H  OC.sub.2 H.sub.5                    OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCH.sub.2 CF.sub.3                    OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  CF.sub.3                    OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  CH.sub.2 F                    OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  CH.sub.2 Cl                    OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  CH.sub.2 Br                    OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  F       OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  I       OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCH.sub.2 CH.sub.2 F                    OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCH.sub.2 CH.sub.2 CF.sub.3                    OCH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCH.sub.2 CHF.sub.2                    CH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCH.sub.2 CF.sub.3                    CH.sub.3H     CH.sub.2 CH.sub.2 F         H  Cl      OC.sub.2 H.sub.5H     CH.sub.2 CH.sub.2 F         H  OC.sub.2 H.sub.5                    NHCH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCH.sub.3                    CH.sub.2 SCH.sub.3H     CH.sub.2 CH.sub.2 F         H  OCF.sub.2 H                    CH.sub.3H     CH.sub. 2 CH.sub.2 F         H  Cl      OCF.sub.2 HH     CH.sub.2 Cl         H  OCH.sub.3                    OCH.sub.3      108-110H     CH.sub.2 Cl         H  CH.sub.3                    OCH.sub.3H     CH.sub.2 Cl         H  CH.sub.3                    CH.sub.3       124-125H     CH.sub.2 Cl         H  Cl      OCH.sub.3H     CH.sub.2 Cl         H  Br      OCH.sub.3H     CH.sub.2 Cl         H  CH.sub.3                    HH     CH.sub.2 Cl         H  OCH.sub.3                    HH     CH.sub.2 Cl         H  OCH.sub.3                    CH.sub.2 OC.sub.2 H.sub.5H     CH.sub.2 Cl         H  OCF.sub.2 H                    OCH.sub.3H     CH.sub.2 Cl         H  OCH.sub.3                    CH(OCH.sub.3).sub.2H     CH.sub.2 Cl         H  CH.sub.3                    OC.sub.2 H.sub.5H     CH.sub.2 Cl         H  CH.sub.3                    CH.sub.2 OCH.sub.3H     CH.sub.2 Cl         H  OCH.sub.3                    CH.sub.2 OCH.sub.3H     CH.sub.2 Cl         H  OCH.sub.3                    C.sub.2 H.sub.5H     CH.sub.2 Cl         H  OC.sub.2 H.sub.5                    OCH.sub.3H     CH.sub.2 Cl         H  OCH.sub.2 CF.sub.3                    OCH.sub.3H     CH.sub.2 Cl         H  CF.sub.3                    OCH.sub.3H     CH.sub.2 Cl         H  CH.sub.2 F                    OCH.sub.3H     CH.sub.2 Cl         H  CH.sub.2 Cl                    OCH.sub. 3H     CH.sub.2 Cl         H  CH.sub.2 Br                    OCH.sub.3H     CH.sub.2 Cl         H  F       OCH.sub.3H     CH.sub.2 Cl         H  I       OCH.sub.3H     CH.sub.2 Cl         H  OCH.sub.2 CH.sub.2 F                    OCH.sub.3H     CH.sub.2 Cl         H  OCH.sub.2 CH.sub.2 CF.sub.3                    OCH.sub.3H     CH.sub.2 Cl         H  OCH.sub.2 CHF.sub.2                    CH.sub.3H     CH.sub.2 Cl         H  OCH.sub.2 CF.sub.3                    CH.sub.3H     CH.sub.2 Cl         H  Cl      OC.sub.2 H.sub.5H     CH.sub.2 Cl         H  OC.sub.2 H.sub.5                    NHCH.sub.3H     CH.sub.2 Cl         H  OCH.sub.3                    CH.sub.2 SCH.sub.3H     CH.sub.2 Cl         H  OCF.sub.2 H                    CH.sub.3H     CH.sub.2 Cl         H  Cl      OCF.sub.2 HH     CHClCH.sub.3         H  OCH.sub.3                    OCH.sub.3H     CHClCH.sub.3         H  CH.sub.3                    OCH.sub.3      137-139H     CHClCH.sub.3         H  CH.sub.3                    CH.sub.3       141-143H     CHClCH.sub.3         H  Cl      OCH.sub.3H     CHClCH.sub.3         H  Br      OCH.sub.3H     CHClCH.sub.3         H  CH.sub.3                    HH     CHClCH.sub.3         H  OCH.sub.3                    HH     CHClCH.sub.3         H  OCH.sub.3                    CH.sub.2 OC.sub.2 H.sub.5H     CHClCH.sub.3         H  OCF.sub.2 H                    OCH.sub.3H     CHClCH.sub.3         H  OCH.sub.3                    CH(OCH.sub.3).sub.2H     CHClCH.sub.3         H  CH.sub.3                    OC.sub.2 H.sub.5H     CHClCH.sub.3         H  CH.sub.3                    CH.sub.2 OCH.sub.3H     CHClCH.sub.3         H  OCH.sub.3                    CH.sub.2 OCH.sub.3H     CHClCH.sub.3         H  OCH.sub.3                    C.sub.2 H.sub.5H     CHClCH.sub.3         H  OC.sub.2 H.sub.5                    OCH.sub.3H     CHClCH.sub.3         H  OCH.sub.2 CF.sub.3                    OCH.sub.3H     CHClCH.sub.3         H  CF.sub.3                    OCH.sub.3H     CHClCH.sub.3         H  CH.sub.2 F                    OCH.sub.3H     CHClCH.sub.3         H  CH.sub.2 Cl                    OCH.sub.3H     CHClCH.sub.3         H  CH.sub.2 Br                    OCH.sub.3H     CHClCH.sub.3         H  F       OCH.sub.3H     CHClCH.sub.3         H  I       OCH.sub.3H     CHClCH.sub.3         H  OCH.sub.2 CH.sub.2 F                    OCH.sub.3H     CHClCH.sub.3         H  OCH.sub.2 CH.sub.2 CF.sub.3                    OCH.sub.3H     CHClCH.sub.3         H  OCH.sub.2 CHF.sub.2                    CH.sub.3H     CHClCH.sub.3         H  OCH.sub.2 CF.sub.3                    CH.sub.3H     CHClCH.sub.3         H  Cl      OC.sub.2 H.sub.5H     CHClCH.sub.3         H  OC.sub.2 H.sub.5                    NHCH.sub.3H     CHClCH.sub.3         H  OCH.sub.3                    CH.sub.2 SCH.sub.3H     CHClCH.sub.3         H  OCF.sub.2 H                    CH.sub.3H     CHClCH.sub.3         H  Cl      OCF.sub.2 HH     CH.sub.2 Br         H  OCH.sub.3                    OCH.sub.3H     CH.sub.2 Br         H  CH.sub.3                    OCH.sub.3H     CH.sub.2 Br         H  CH.sub.3                    CH.sub.3H     CH.sub.2 Br         H  Cl      OCH.sub.3H     CH.sub.2 Br         H  Br      OCH.sub.3H     CH.sub.2 Br         H  CH.sub.3                    HH     CH.sub.2 Br         H  OCH.sub.3                    HH     CH.sub.2 Br         H  OCH.sub.3                    CH.sub.2 OC.sub.2 H.sub.5H     CH.sub.2 Br         H  OCF.sub.2 H                    OCH.sub.3H     CH.sub.2 Br         H  OCH.sub.3                    CH(OCH.sub.3).sub.2H     CH.sub.2 Br         H  CH.sub.3                    OC.sub.2 H.sub.5H     CH.sub.2 Br         H  CH.sub.3                    CH.sub.2 OCH.sub.3H     CH.sub.2 Br         H  OCH.sub.3                    CH.sub.2 OCH.sub.3H     CH.sub.2 Br         H  OCH.sub.3                    C.sub.2 H.sub.5H     CH.sub.2 Br         H  OCH.sub.2 CF.sub.3                    OCH.sub.3H     CH.sub.2 Br         H  OC.sub.2 H.sub.5                    OCH.sub.3H     CH.sub.2 Br         H  CF.sub.3                    OCH.sub.3H     CH.sub.2 Br         H  CH.sub.2 F                    OCH.sub.3H     CH.sub.2 Br         H  CH.sub.2 Cl                    OCH.sub.3H     CH.sub. 2 Br         H  CH.sub.2 Br                    OCH.sub.3H     CH.sub.2 Br         H  F       OCH.sub.3H     CH.sub.2 Br         H  I       OCH.sub.3H     CH.sub.2 Br         H  OCH.sub.2 CH.sub.2 F                    OCH.sub.3H     CH.sub.2 Br         H  OCH.sub.2 CH.sub.2 CF.sub.3                    OCH.sub.3H     CH.sub.2 Br         H  OCH.sub.2 CHF.sub.2                    CH.sub.3H     CH.sub.2 Br         H  OCH.sub.2 CF.sub.3                    CH.sub.3H     CH.sub.2 Br         H  Cl      OC.sub.2 H.sub.5H     CH.sub.2 Br         H  OC.sub.2 H.sub.5                    NHCH.sub.3H     CH.sub.2 Br         H  OCH.sub.3                    CH.sub.2 SCH.sub.3H     CH.sub.2 Br         H  OCF.sub.2 H                    CH.sub.3H     CH.sub.2 Br         H  Cl      OCF.sub.2 HH     CHF.sub.2         H  OCH.sub.3                    OCH.sub.3      184-186H     CHF.sub.2         H  CH.sub.3                    OCH.sub.3      166-167H     CHF.sub.2         H  CH.sub.3                    CH.sub.3H     CHF.sub.2         H  Cl      OCH.sub.3H     CHF.sub.2         H  Br      OCH.sub.3H     CHF.sub.2         H  CH.sub.3                    HH     CHF.sub.2         H  OCH.sub.3                    HH     CHF.sub.2         H  OCH.sub.3                    CH.sub.2 OC.sub.2 H.sub.5H     CHF.sub.2         H  OCF.sub.2 H                    OCH.sub.3H     CHF.sub.2         H  OCH.sub.3                    CH(OCH.sub.3).sub.2H     CHF.sub.2         H  CH.sub.3                    OC.sub.2 H.sub.5H     CHF.sub.2         H  CH.sub.3                    CH.sub.2 OCH.sub.3H     CHF.sub.2         H  OCH.sub.3                    CH.sub.2 OCH.sub.3H     CHF.sub.2         H  OCH.sub.3                    C.sub.2 H.sub.5H     CHF.sub.2         H  OC.sub.2 H.sub.5                    OCH.sub.3H     CHF.sub.2         H  OCH.sub.2 CF.sub.3                    OCH.sub.3H     CHF.sub.2         H  CF.sub.3                    OCH.sub.3H     CHF.sub.2         H  CH.sub.2 F                    OCH.sub.3H     CHF.sub.2         H  CH.sub.2 Cl                    OCH.sub.3H     CHF.sub.2         H  CH.sub.2 Br                    OCH.sub.3H     CHF.sub.2         H  F       OCH.sub.3H     CHF.sub.2         H  I       OCH.sub.3H     CHF.sub.2         H  OCH.sub.2 CH.sub.2 F                    OCH.sub.3H     CHF.sub.2         H  OCH.sub.2 CH.sub.2 CF.sub.3                    OCH.sub.3H     CHF.sub.2         H  OCH.sub.2 CHF.sub.2                    CH.sub.3H     CHF.sub.2         H  OCH.sub.2 CF.sub.3                    CH.sub.3H     CHF.sub.2         H  Cl      OC.sub.2 H.sub.5H     CHF.sub.2         H  OC.sub.2 H.sub.5                    NHCH.sub.3H     CHF.sub.2         H  OCH.sub.3                    CH.sub.2 SCH.sub.3H     CHF.sub.2         H  OCF.sub.2 H                    CH.sub.3H     CHF.sub.2         H  Cl      OCF.sub.2 HH     CHFCl   H  OCH.sub.3                    OCH.sub.3H     CHFCl   H  CH.sub.3                    OCH.sub.3H     CHFCl   H  CH.sub.3                    CH.sub.3H     CHFCl   H  Cl      OCH.sub.3H     CHFCl   H  Br      OCH.sub.3H     CHFCl   H  CH.sub.3                    HH     CHFCl   H  OCH.sub.3                    HH     CHFCl   H  OCH.sub.3                    CH.sub.2 OC.sub.2 H.sub.5H     CHFCl   H  OCF.sub.2 H                    OCH.sub.3H     CHFCl   H  OCH.sub.3                    CH(OCH.sub.3).sub.2H     CHFCl   H  CH.sub.3                    OC.sub.2 H.sub.5H     CHFCl   H  CH.sub.3                    CH.sub.2 OCH.sub.3H     CHFCl   H  OCH.sub.3                    CH.sub.2 OCH.sub.3H     CHFCl   H  OCH.sub.3                    C.sub.2 H.sub.5H     CHFCl   H  OCH.sub.2 CF.sub.3                    OCH.sub.3H     CHFCl   H  OC.sub.2 H.sub.5                    OCH.sub.3H     CHFCl   H  CF.sub.3                    OCH.sub.3H     CHFCl   H  CH.sub.2 F                    OCH.sub.3H     CHFCl   H  CH.sub.2 Cl                    OCH.sub.3H     CHFCl   H  CH.sub.2 Br                    OCH.sub.3H     CHFCl   H  F       OCH.sub.3H     CHFCl   H  I       OCH.sub.3H     CHFCl   H  OCH.sub.2 CH.sub.2 F                    OCH.sub.3H     CHFCl   H  OCH.sub.2 CH.sub.2 CF.sub.3                    OCH.sub.3H     CHFCl   H  OCH.sub.2 CHF.sub.2                    CH.sub.3H     CHFCl   H  OCH.sub.2 CF.sub.3                    CH.sub.3H     CHFCl   H  Cl      OC.sub.2 H.sub.5H     CHFCl   H  OC.sub.2 H.sub.5                    NHCH.sub.3H     CHFCl   H  OCH.sub.3                    CH.sub.2 SCH.sub.3H     CHFCl   H  OCF.sub.2 H                    CH.sub.3H     CHFCl   H  Cl      OCF.sub.2 HH     CHFCl   H  n-C.sub.3 H.sub.7                    OCH.sub.3H     CHFCl   H  OCH.sub.3                    NHCH.sub.3H     CHFCl   H  OCH.sub.3                    N(CH.sub.3).sub.2H     CHFCl   H  OCH.sub.3                    cyclopropylH     CHFCl   H  OCH.sub.3                    OCH.sub.2 CH.sub.2 OCH.sub.3H     CHFCl   H  OC.sub.2 H.sub.5                    CH.sub.2 SCH.sub.3H     CHFCl   H  OCH.sub.3                    CH(SCH.sub.3)OC.sub.2 H.sub.5H     CHFCl   H  OCH.sub.3                    CH(SC.sub.2 H.sub.5).sub.2H     CHFCl   H  OCH.sub.3                    1,3-dioxolan-2-ylH     CHFCl   H  OCH.sub.3                    N(OCH.sub.3)CH.sub.3H     CHFCl   H  OCH.sub.3                    C.sub.2 H.sub.5H     CHFCl   H  OCH.sub.3                    CF.sub.35-F   CH.sub.2 F         H  OCH.sub.3                    OCH.sub.36-Cl  CH.sub.2 F         H  OCH.sub.3                    OCH.sub.36-Cl  CH.sub.2 Cl         H  OCH.sub.3                    OCH.sub.36-Cl  CH.sub.2 F         H  CH.sub.3                    OCH.sub.36-Cl  CH.sub.2 F         H  CH.sub.3                    CH.sub.36-Cl  CH.sub.2 F         H  Cl      OCH.sub.35-Br  CH.sub.2 F         H  OCH.sub.3                    OCH.sub.35-CH.sub.2 CN CH.sub.2 F         H  OCH.sub.3                    OCH.sub.35-OCH.sub.3 CH.sub.2 F         H  OCH.sub.3                    OCH.sub.35-SCH.sub.3 CH.sub.2 F         H  OCH.sub.3                    OCH.sub.35-OCF.sub.2 H CH.sub.2 F         H  OCH.sub.3                    OCH.sub.3H     CH.sub.2 F         CH.sub.3            OCH.sub.3                    OCH.sub.3H     CH.sub.2 F         CH.sub.3            CH.sub.3                    OCH.sub.3H     CH.sub.2 Cl         CH.sub.3            OCH.sub.3                    OCH.sub.3H     CHF.sub.2         CH.sub.3            OCH.sub.3                    OCH.sub.3H     CH.sub.2 Br         CH.sub.3            OCH.sub.3                    OCH.sub.36-Cl  CH.sub.2 Cl         CH.sub.3            OCH.sub.3                    OCH.sub.3__________________________________________________________________________ 
    
     
                       TABLE 2______________________________________ ##STR23##                                     mpR.sup.1 R.sup.2   R.sup.3                    X      Y         (°C.)______________________________________H       CH.sub.2 F             H      CH.sub.3                           OCH.sub.3H       CH.sub.2 F             H      OCH.sub.3                           OCH.sub.3 119-                                     122H       CH.sub.2 F             H      OC.sub.2 H.sub.5                           NHCH.sub.3H       CH.sub.2 F             H      OCH.sub.3                           N(OCH.sub.3)(CH.sub.3)H       CH.sub.2 F             H      OCH.sub.3                           N(CH.sub.3).sub.2H       CH.sub.2 Cl             H      CH.sub.3                           OCH.sub.3H       CH.sub.2 Cl             H      OCH.sub.3                           OCH.sub.3H       CH.sub.2 Cl             H      OC.sub.2 H.sub.5                           NHCH.sub.3H       CH.sub. 2 Cl             H      OCH.sub.3                           N(OCH.sub.3)(CH.sub.3)H       CH.sub.2 Cl             H      OCH.sub.3                           N(CH.sub.3).sub.2H       CH.sub.2 Br             H      CH.sub.3                           OCH.sub.3H       CH.sub.2 Br             H      OCH.sub.3                           OCH.sub.3H       CH.sub.2 Br             H      OC.sub.2 H.sub.5                           NHCH.sub.3H       CH.sub.2 Br             H      OCH.sub.3                           N(OCH.sub.3)(CH.sub.3)H       CH.sub.2 Br             H      OCH.sub.3                           N(CH.sub.3).sub.2H       CHF.sub.2 H      CH.sub.3                           OCH.sub.3H       CHF.sub.2 H      OCH.sub.3                           OCH.sub.3H       CHF.sub.2 H      OC.sub.2 H.sub.5                           NHCH.sub.3H       CHF.sub.2 H      OCH.sub.3                           N(OCH.sub.3)(CH.sub.3)H       CHF.sub.2 H      OCH.sub.3                           N(CH.sub.3).sub.2H       CH.sub.2 F             CH.sub.3                    OCH.sub.3                           OCH.sub.3H       CH.sub.2 Cl             CH.sub.3                    OCH.sub.3                           OCH.sub.3H       CH.sub.2 F             CH.sub.3                    CH.sub.3                           OCH.sub.3H       CH.sub.2 Br             CH.sub.3                    OCH.sub.3                           OCH.sub.3H       CH.sub.2 Cl             CH.sub.3                    CH.sub.3                           OCH.sub.3H       CH.sub.2 Br             CH.sub.3                    CH.sub.3                           OCH.sub.3H       CHF.sub.2 CH.sub.3                    OCH.sub.3                           OCH.sub.3H       CHF.sub.2 CH.sub.3                    CH.sub.3                           OCH.sub.3H       CH.sub. 2 F             CH.sub.3                    OC.sub.2 H.sub.5                           NHCH.sub.3H       CH.sub.2 F             CH.sub.3                    OCH.sub.3                           N(CH.sub.3).sub.2H       CHFCH.sub.3             H      CH.sub.3                           OCH.sub.3H       CHFCH.sub.3             H      OCH.sub.3                           OCH.sub.3H       CHFCH.sub.3             H      OC.sub.2 H.sub.5                           NHCH.sub.3H       CHFCH.sub.3             H      OCH.sub.3                           N(OCH.sub.3)(CH.sub.3)H       CHFCH.sub.3             H      OCH.sub.3                           N(CH.sub.3).sub.2H       CHClCH.sub.3             H      CH.sub.3                           OCH.sub.3H       CHClCH.sub.3             H      OCH.sub.3                           OCH.sub.3H       CHClCH.sub.3             H      OC.sub.2 H.sub.5                           NHCH.sub.3H       CHClCH.sub.3             H      OCH.sub.3                           N(OCH.sub.3)(CH.sub.3)H       CHClCH.sub.3             H      OCH.sub.3                           N(CH.sub.3).sub.2H       CH.sub.2 CH.sub.2 F             H      CH.sub.3                           OCH.sub.3H       CH.sub.2 CH.sub.2 F             H      OCH.sub.3                           OCH.sub.3H       CH.sub.2 CH.sub.2 F             H      OC.sub.2 H.sub.5                           NHCH.sub.3H       CH.sub.2 CH.sub.2 F             H      OCH.sub.3                           N(OCH.sub.3)(CH.sub.3)H       CH.sub.2 CH.sub.2 F             H      OCH.sub.3                           N(CH.sub.3).sub.2H       CHFCl     H      OCH.sub.3                           OCH.sub.3H       CHFCl     H      CH.sub.3                           OCH.sub.3H       CHFCl     H      CH.sub.3                           CH.sub.3H       CHFCl     H      Cl     OCH.sub.3H       CHFCl     H      OCH.sub.3                           CH.sub.2 OCH.sub.3H       CHFCl     H      CH.sub.3                           OC.sub.2 H.sub.5H       CHFCl     H      CH.sub.2 Cl                           OCH.sub.3H       CHFCl     H      F      OCH.sub.3H       CHFCl     H      OCH.sub.3                           CH(OCH.sub.3).sub.2H       CHFCl     H      OCHF.sub.2                           OCH.sub.3H       CHFCl     H      C.sub.2 H.sub.5                           OCH.sub.35-F     CH.sub.2 F             H      CH.sub.3                           OCH.sub.36-Cl    CH.sub.2 F             H      OCH.sub.3                           CH.sub.35-Br    CH.sub.2 F             H      CH.sub.3                           OCH.sub.35-CH.sub.2 CN   CH.sub.2 F             H      OCH.sub.3                           OCH.sub.35-OCH.sub.3   CH.sub.2 F             H      CH.sub.3                           OCH.sub.35-SCH.sub.3   CH.sub.2 F             H      CH.sub.3                           OCH.sub.35-OCF.sub.2 H   CH.sub.2 F             H      CH.sub.3                           OCH.sub.36-Cl    CH.sub.2 Cl             H      CH.sub.3                           OCH.sub.36-Cl    CH.sub.2 Br             H      OCH.sub.3                           OCH.sub.36-Cl    CH.sub.2 F             H      OC.sub.2 H.sub.5                           NHCH.sub.36-Cl    CH.sub.2 F             H      OCH.sub.3                           OCH.sub.3______________________________________ 
    
     
                       TABLE 3______________________________________ ##STR24##R.sup.1 R.sup.2    R.sup.3                     X.sup.1 Y.sup.1                                  mp (°C.)______________________________________H       CH.sub.2 F H      CH.sub.3                             OH       CH.sub.2 F H      OCH.sub.3                             OH       CH.sub.2 F H      OC.sub.2 H.sub.5                             OH       CH.sub.2 F H      OCF.sub.2 H                             OH       CH.sub.2 F H      OCH.sub.3                             CH.sub.2H       CH.sub.2 Cl              H      CH.sub.3                             OH       CH.sub.2 Cl              H      OCH.sub.3                             OH       CH.sub.2 Br              H      CH.sub.3                             OH       CHFCH.sub.3              H      CH.sub.3                             OH       CHClCH.sub.3              H      CH.sub.3                             O5-OCH.sub.3   CH.sub.2 F H      CH.sub.3                             O6-Cl    CH.sub.2 F H      CH.sub.3                             O3-CH.sub.3   CH.sub.2 F H      CH.sub.3                             O5-CH.sub.2 CN   CH.sub.2 F H      CH.sub.3                             OH       CH.sub.2 F CH.sub.3                     CH.sub.3                             OH       CHF.sub.2  H      OCH.sub.3                             O______________________________________ 
    
     
                       TABLE 4______________________________________ ##STR25##R.sup.1    R.sup.2    R.sup.3 X.sup.1 mp (°C.)______________________________________H          CH.sub.2 F H       CH.sub.3H          CH.sub.2 F H       OCH.sub.3H          CH.sub.2 F H       OC.sub.2 H.sub.5H          CH.sub.2 F H       OCF.sub.2 HH          CH.sub.2 Cl                 H       CH.sub.3H          CH.sub.2 Cl                 H       OCH.sub.3H          CH.sub.2 Br                 H       CH.sub.3H          CHF.sub.2  H       CH.sub.3H          CHF.sub.2  H       OCH.sub.3H          CHFCH.sub.3                 H       CH.sub.3H          CHFCH.sub.3                 H       OCH.sub.3H          CHFCl      H       OCH.sub.3H          CHFCl      H       CH.sub.36-Cl       CHFCl      H       CH.sub.36-Cl       CHFCl      H       OCH.sub.36-Cl       CH.sub.2 F H       CH.sub.36-Cl       CH.sub.2 F H       OCH.sub.35-CH.sub.2 CN      CH.sub.2 F H       CH.sub.35-OCH.sub.3      CH.sub.2 F H       CH.sub.3H          CH.sub.2 F CH.sub.3                         CH.sub.3H          CH.sub.2 F CH.sub.3                         OCH.sub.3H          CHClCH.sub.3                 H       OCH.sub.3H          CH.sub.2 CH.sub.2 F                 H       OCH.sub.3______________________________________ 
    
     
                       TABLE 5______________________________________ ##STR26##R.sup.1 R.sup.2    R.sup.3                    X.sup.1 Y.sup.3                                  mp (°C.)______________________________________H       CH.sub.2 F H     CH.sub.3                            CH.sub.3H       CH.sub.2 F H     OCH.sub.3                            CH.sub.3H       CH.sub.2 F H     OC.sub.2 H.sub.5                            CH.sub.3H       CH.sub.2 F H     OCF.sub.2 H                            CH.sub.3H       CH.sub.2 F H     OCH.sub.3                            HH       CH.sub.2 F H     CH.sub.3                            HH       CH.sub.2 Cl              H     OCH.sub.3                            OCH.sub.3H       CHFCl      H     OCH.sub.3                            OCH.sub.3H       CHFCl      H     OCH.sub.3                            CH.sub.3H       CHFCH.sub.3              H     OCH.sub.3                            OCH.sub.3H       CHF.sub.2  H     OCH.sub.3                            OCH.sub.36-F     CH.sub.2 F H     OCH.sub.3                            OCH.sub.35-OCH.sub.3   CH.sub.2 F H     OCH.sub.3                            OCH.sub.36-Cl    CH.sub.2 F H     OCH.sub.3                            OCH.sub.33-CH.sub.3   CH.sub.2 F H     OCH.sub.3                            OCH.sub.35-CH.sub.2 CN   CH.sub.2 F H     OCH.sub.3                            CH.sub.3H       CH.sub.2 Cl              H     OCH.sub.3                            CH.sub.3H       CH.sub.2 Br              H     OCH.sub.3                            CH.sub.3H       CH.sub.2 CH.sub.2 F              H     OCH.sub.3                            CH.sub.3H       CHClCH.sub.3              H     OCH.sub.3                            CH.sub.3H       CHF.sub.2  H     OCH.sub.3                            CH.sub.36-Cl    CH.sub.2 F H     OCH.sub.3                            CH.sub.3______________________________________ 
    
     
                       TABLE 6______________________________________ ##STR27##R.sup.1  R.sup.2   R.sup.3                     X.sup.2                            Y.sup.2                                   mp (°C.)______________________________________H        CH.sub.2 F              H      CH.sub.3                            OCH.sub.3H        CH.sub.2 F              H      CH.sub.3                            OC.sub.2 H.sub.5H        CH.sub.2 F              H      CH.sub.3                            SCH.sub.3H        CH.sub.2 F              H      CH.sub.3                            SC.sub.2 H.sub.5H        CH.sub.2 F              H      CH.sub.3                            CH.sub.3H        CH.sub.2 F              H      CH.sub.3                            C.sub.2 H.sub.5H        CH.sub.2 F              H      C.sub.2 H.sub.5                            OCH.sub.3H        CH.sub.2 F              H      CH.sub.2 CF.sub.3                            OCH.sub.3H        CH.sub.2 Cl              H      CH.sub.3                            OCH.sub.3H        CHFCl     H      CH.sub.3                            OCH.sub.3H        CHF.sub. 2              H      CH.sub.3                            OCH.sub.33-CH.sub.3    CH.sub.2 F              H      CH.sub.3                            OCH.sub.36-F      CH.sub.2 F              H      CH.sub.3                            OCH.sub.36-Cl     CH.sub.2 F              H      CH.sub.3                            OCH.sub.35-OCH.sub.3    CH.sub.2 F              H      CH.sub.3                            OCH.sub.36-Cl     CH.sub.2 F              H      CH.sub.3                            CH.sub.35-CH.sub.2 CN    CH.sub.2 F              H      CH.sub.3                            OCH.sub.3H        CH.sub.2 Br              H      CH.sub.3                            OCH.sub.3H        CH.sub.2 CH.sub.2 F              H      CH.sub.3                            OCH.sub.3H        CHFCl     H      CH.sub.3                            CH.sub.3H        CHFCH.sub.3              H      CH.sub.3                            OCH.sub.3H        CHClCH.sub.3              H      CH.sub.3                            OCH.sub.3______________________________________ 
    
     
                       TABLE 7______________________________________ ##STR28##R.sup.1    R.sup.2    R.sup.3 X.sup.3                               mp (°C.)______________________________________H          CH.sub.2 F H       CH.sub.3H          CH.sub.2 F H       OCH.sub.3H          CH.sub.2 Cl                 H       CH.sub.3H          CH.sub.2 Cl                 H       OCH.sub.3H          CHF.sub.2  H       OCH.sub.3H          CHF.sub.2  H       CH.sub.3H          CHFCl      H       CH.sub.3H          CHFCl      H       OCH.sub.3H          CHFCH.sub.3                 H       CH.sub.3H          CHFCH.sub.3                 H       OCH.sub.3H          CHClCH.sub.3                 H       OCH.sub.36-F        CH.sub.2 F H       OCH.sub.36-Cl       CH.sub.2 F H       OCH.sub.33-CH.sub.3 CH.sub.2 F H       CH.sub.35-OCH.sub.3      CH.sub.2 F H       CH.sub.35-CH.sub.2 CN      CH.sub.2 F H       CH.sub.36-Cl       CH.sub.2 F H       OCH.sub.3H          CH.sub.2 CH.sub.2 F                 H       OCH.sub.3H          CH.sub.2 F CH.sub.3                         OCH.sub.3H          CH.sub.2 CH.sub.2 F                 H       CH.sub.3______________________________________ 
    
     
                       TABLE 8______________________________________ ##STR29##R.sup.1 R.sup.2   R.sup.3 X.sup.4 Y.sup.4                                   Z.sup.1                                        mp______________________________________H       CH.sub.2 F             H       CH.sub.3                             CH.sub.3                                   CHH       CH.sub.2 F             H       CH.sub.3                             CH.sub.3                                   NH       CH.sub.2 F             H       OCH.sub.3                             CH.sub.3                                   CHH       CH.sub.2 F             H       OCH.sub.3                             CH.sub.3                                   NH       CH.sub.2 F             H       OCH.sub.3                             OCH.sub.3                                   CHH       CH.sub.2 F             H       OCH.sub.3                             OCH.sub.3                                   NH       CH.sub.2 F             H       Cl      CH.sub.3                                   CHH       CH.sub.2 F             H       OCH.sub.3                             Cl    CHH       CH.sub.2 F             H       OC.sub.2 H.sub.5                             CH.sub.3                                   CHH       CH.sub.2 F             H       CH.sub.2 OCH.sub.3                             CH.sub.3                                   NH       CH.sub.2 F             H       CH.sub.2 OCH.sub.3                             OCH.sub.3                                   CHH       CH.sub.2 F             H       OC.sub.2 H.sub.5                             OC.sub.2 H.sub.5                                   NH       CH.sub.2 Cl             H       OCH.sub.3                             CH.sub.3                                   CHH       CH.sub.2 Cl             H       OCH.sub.3                             OCH.sub.3                                   CHH       CH.sub.2 Cl             H       OCH.sub.3                             CH.sub.3                                   NH       CH.sub.2 Cl             H       OCH.sub.3                             OCH.sub.3                                   NH       CHF.sub.2 H       OCH.sub.3                             CH.sub.3                                   CHH       CHFCl     H       OCH.sub.3                             CH.sub.3                                   CHH       CHFCH.sub.3             H       OCH.sub.3                             CH.sub.3                                   CHH       CHClCH.sub.3             H       OCH.sub.3                             CH.sub.3                                   CH6-F     CH.sub.2 F             H       OCH.sub.3                             CH.sub.3                                   CH3-CH.sub.3   CH.sub.2 F             H       OCH.sub.3                             CH.sub.3                                   CH5-OCH.sub.3   CH.sub.2 F             H       OCH.sub.3                             CH.sub.3                                   CH6-Cl    CH.sub.2 F             H       OCH.sub.3                             CH.sub.3                                   CH5-CH.sub.2 CN   CH.sub.2 F             H       OCH.sub.3                             CH.sub.3                                   CHH       CH.sub.2 F             CH.sub.3                     OCH.sub.3                             CH.sub.3                                   CHH       CH.sub.2 CH.sub.2 F             H       OCH.sub.3                             CH.sub.3                                   CHH       CH.sub.2 CH.sub.2 Cl             H       OCH.sub.3                             CH.sub.3                                   CHH       CHFCl     H       OCH.sub.3                             OCH.sub.3                                   CH______________________________________ 
    
     
                       TABLE 9______________________________________ ##STR30##R.sup.1 R.sup.2   R.sup.3 W   X      Y     Z.sup.1______________________________________H       CH.sub.2 F             H       S   OCH.sub.3                                OCH.sub.3                                      CHH       CH.sub.2 F             H       S   CH.sub.3                                OCH.sub.3                                      NH       CH.sub.2 F             H       S   OCH.sub.3                                OCH.sub.3                                      NH       CH.sub.2 Cl             H       S   OCH.sub.3                                OCH.sub.3                                      CHH       CH.sub.2 Br             H       S   OCH.sub.3                                OCH.sub.3                                      CHH       CHF.sub.2 H       S   OCH.sub.3                                OCH.sub.3                                      CHH       CHFCl     H       S   OCH.sub.3                                OCH.sub.3                                      CHH       CHFCH.sub.3             H       S   OCH.sub.3                                OCH.sub.3                                      CHH       CHClCH.sub.3             H       S   OCH.sub.3                                OCH.sub.3                                      CH5-OCH.sub. 3   CH.sub.2 F             H       S   OCH.sub.3                                OCH.sub.3                                      CH6-Cl    CH.sub.2 F             H       S   OCH.sub.3                                OCH.sub.3                                      CHH       CH.sub.2 F             CH.sub.3                     S   OCH.sub.3                                OCH.sub.3                                      CHH       CH.sub.2 F             H       S   OCH.sub.3                                CH.sub.3                                      CH______________________________________ 
    
     Test results indicate that the compounds of the present invention are highly active pre-emergent or post-emergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or post-emergency weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as wheat and barley. Alternatively, the subject compounds are useful to modify plant growth. 
     The rates of application for the compounds of the present invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formations selected, mode of application, amount of foliage present, etc. 
     In general terms, the subject compounds should be applied at levels of around 0.05 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modifications or for situations where only short-term persistence is required. 
     Formulations 
     Useful formulations of the compounds of formula(I) can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. 
     Sprayable formulations can be extented in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (1) about 0.1% to 20% surfactant(s) and (2) about 1% to 99% solid or liquid inert diluent(s). More specially, they will contain these ingredients in the following approximate proportions: 
     
         ______________________________________       Active  Weight Percent*Formulations  Ingredient                   Diluent(s)                             Surfactant(s)______________________________________Wettable Powders         20-90      0-74     1-10Oil Suspensions,          3-50     40-95     0-15Emulsions, Solutions(including Emulsifiableconcentrates)Aqueous Suspension         10-50     40-84     1-20Dusts          1-25     70-99     0-5Granules and Pellets         0.1-95      5-99.9  0-15High Strength Composi-         90-99      0-10     0-2tions______________________________________ *Active ingredient plus at least one of a surfactant or a diluent equals 100 weight percent. 
    
     Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactants to activate ingredient are sometimes desirable, and are achieved by incorporation into the formation or by tank mixing. 
     Typical solid diluents are described in Watkins, et al., &#34;Handbook of Insecticide Dust Diluents and Carriers&#34;, 2nd Ed., Dorland Books, Caldwell, N.J. but other solids, either mined or monufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. 
     Typical liquid diluents and solvents are described in Marsden, &#34;Solvent Guide&#34;, 2Nd Ed. Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; Solution concentrates are preferably stable against phase separation at 0° C. &#34;McCutcheon&#39;s Detergents and Emulsifiers Annual&#34;, M C Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, &#34;Encyclopedia of Surface Active Agents&#34;, Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. 
     All formulations can contain miner amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. 
     The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. 
     See J. E. Browning, &#34;Agglomeration&#34;, Chemical Engineering, Dec. 4, 1967, pp, 147ff. and &#34;Perry&#39;s chemical Engineer&#39;s Handbook&#34;, 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff. 
     For further information regarding the art of formulation, see for example: 
     H. M. Loux, U.S. Pat. No. 3,235,361 Feb. 15, 1966, lCol. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; H. Gysin and E. Knusli, U.S. Pat. No. 2,981,855, Jun. 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; G. C. Klingman, &#34;Weed Control as a Science&#34;, John Wiley and S. A. Evans, &#34;Weed control Handbook&#34;, 5Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. 
     The compounds of the present invention can be used independently and may be used in combination with any other commercial herbicide. A summary of the possible combination herbicides is given below 
     
         ______________________________________Common Name______________________________________acetochlor   acifluorfen   AC 252,214AC 263,499   acrolein      alachlorametryn      amitrole      AMSasulam       assure        atrazineBAS-514      barban        benefinbensulfuron methyl        bensulide     bentazonbenzofluor   benzoylprop   bifenoxbromacil     bromoxynil    butachlorbuthidazole  butralin      butylatecacodylic acid        CDAA          CDECCGA 82725    CH-83         chlorambenchlorbromuron        chlorimuron ethyl                      chloroxuronchlorpropham chlorsulfuron chlortoluroncinmethylin  clethodim     clomazonecloproxydim  clopyralid    CMAcyanzine     cycloate      cycluroncyperquat    cyprazine     cyprazolecypromid     dalapon       dazometDCPA         desmediphan   desmetryndiallate     dicamba       dichlorbenildichlorprop  dichlofop     diethatyldifenzoquat  dinitramine   dinosebdiphenamid   dipropetryn   diquatdiuron       DNOC          DOWCO453MEDPX-M6316    DSMA          endothallEPTC         ethalfluralin ethoxfumesateExpress      fenac         fenoxaprop ethylfenuron      fenuron TCA   flampropfluazifop    fluazifop-butyl                      fluazifop-Pfluchloralin fluometuron   fluorochloridonefluorodifen  fluoroglycofen                      fluridonefomesafen    fosamine      glyphosatehaloxyfop    harmoney      hexafluratehexazinone   HW-52         imazamethabenzimazapyr     imazaquin     imazethapyrioxynil      isopropalin   isoproturonisouron      isoxaben      karbutilatelactofen     lenacil       linuronMAA          MAMA          MCPAMCPB         mecoprop      mefluididemethalpropalin        methabenzthiazuron                      methammethazole    methoxuron    metolachlormetribuzin   metsulfuron methyl                      MHmolinate     monolinuron   monuronmonuron TCA  MSMA          My-93napropamide  naproanilide  naptalamneburon      nitralin      nitrofennitrofluorfen        norea         norfluazonNTN-801      oryzalin      oxadiazonoxyfluorfen  paraquat      pebulatependimethalin        perfluidone   phenmediphampicloram     PPG-1013      pretilachlorprocyazine   profluralin   prometonprometryn    pronamide     propachlorpropanil     propazine     prophamprosulfalin  prynachlor    pyrazonpyrazolate   quizalofop ethyl                      quizalofopSC-2957      secbumeton    sethoxydimsiduron      simazine      SL-49sulfometuron methyl        TCA           tebuthiuronterbacil     terbuchlor    terbuthylazineterbutol     terbutryn     thiameturon methylthiobencarb  triallate     triclopyrtridiphane   trifluralin   trimeturon2,4-D        2,4-DB        vernolateX-52         xylachlor______________________________________ 
    
     EXAMPLE 1: N-t-butyl 2-(fluoroacetyl)benzenesulfonamide 
     N-t-butyl benzenesulfonamide (10 g, 0.407 mol) was dissolved in 100 ml of anhydrous tetrahydrofuran and the solution was cooled to 0° C. under nitrogen atmosphere, and herein 37.6 ml of 2.5N n-butyl lithium was added dropwise. 
     The solution stirred for 2.5 hr at room temperature was cooled to -78° C., and ethyl fluoracetate (5 ml, 0.052 mol) was added dropwise. 
     After slowly raising the reaction temperature, the reaction mixture was stirred for 12 hr at room temperature, and 5% hydrochloride acid and 50 ml of ethyl acetate were added and stirred to separate organic layer. 
     After extracting the water layer with ethylacetate, the combined organic layer was dried with magnesium sulfate, filtered and concentrated. 
     The obtained residue was chromatography through silica gel using 1:3 of ethyl acetate-hexane as eluant to afford 5.3 g of the desired product (white solid, yield: 41%). 
     M.P. : 126° C. 
       1  H NMR (CDCl 3 ): δ1.26(s, 9H), 4.96(s, 1H), 5.16(br s, 1H), 5.73(s, 1H), 7.40-7.80 (m, 3H), 7.93-8.20 (m, 1H). 
     IR (KBr)ν(NH) 3250 cm -1 , ν(C═O) 1700 cm -1   
     EXAMPLE 2: 2-(1-acetoxy-2-fluoroethyl)-N-t-butylbenzenesulfonamide 
     N-t-butyl 2-(fluoroacetyl)benzenesulfonamide (5g, 0.018 mol) was dissolved in 100 ml of methanol, and sodium borohydride (0.7 g, 0.018 mol) was added potionwise in the solution. 
     After stirring for 30 min at 40° C., methanol was evaporated, and then the obtained residue was dissolved in methylene chloride and washed with 5% hydrochloric acid. The separated organic layer was dried, filtered and concentrated to obtain a residue of oil type. 
     The residue was dissolved in 100 ml of methylene chloride and acetic anhydride (1.98 ml, 0.02 mol), pyrimdine (1.6 ml, 0.02 mol) and N,N-dimethylaminopyridine (0.12 g, 0.001 mol) were added. 
     After stirring for 24 hr at room temperature, the solution was washed with 5% hydrochloric acid, and then the organic layer was dried with magnesium sulfate, filtered and concentrated. 
     The obtained residue was chromatographed through silica gel using 1:3 solution of ethyl acetate-hexane to afford 5.24 g of the desired product (white solid, yield: 92%). 
     M.P.: 118°-119° C. 
       1  H NMR (CDCl 3 ): δ1.23(s, 9H), 2.20(s, 3H), 4.20-4.40 (m, 1H), 5.00-5.20(m, 1H), 5.70(br s, 1H), 6.50-7.10(m, 1H), 7.31-7.86(m, 3H), 8.06-8.36(m, 1H). 
     IR (KBr) ν(NH) 3250 cm -1 , ν(C═O) 1720 cm -1   
     EXAMPLE 3: 2-(1-acetoxy-2-fluoroethyl)benzenesulfonamide 
     N-t-butyl 2-(1-acetoxy-2-fluoroethyl)benzenesulfonamide (5.24 g, 0.016 mol) was dissolved in 20 ml of trifluoro acetic acid, and stirred at room temperature for 12 hr. 
     After concentrating the reacted solution under the reduced pressure, the obtained residue was dissolved in methylene chloride, and then the solution was washed one time with 5% sodium bicarbonate solution. The obtained organic layer was dried with magnesium sulfate, filtered and concentrated. 
     The residue was treated with ethylacetate and hexane and crystalized to afford 3 g of the desired product (white solid, yield: 71%). 
     M.P.: 122°-124° C. 
       1  H NMR (CDCl 3 ): δ2.16(s, 3H), 4.20-4.40(m, 1H), 5.00-5.20(m, 1H), 5.70(br s, 2H), 6.46-7.00(m, 1H), 7.60-7.83(m, 3H), 8.06-8.33(m, 1H). 
     IR (KBr) ν(NH 2 ) 3250 cm -1 , 3350 cm -1 , ν(C═O) 1750 cm -1   
     EXAMPLE 4: 2-(1-acetoxy-2-fluoroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]benzenesulfonamide 
     2-(1-acetoxy-2-fluoroethyl)benzenesulfonamide(1.91 g, 0.007 mol) was dissolved in 30 ml of acetonitrile, and herein phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate (2 g, 0.007 mol) was added at room temperature. 
     After adding dropwise 0.9 ml of DBU, the solution was stirred for 30 min, diluted with 100 ml of methylene chloride, and acidified with 5% hydrochloric acid. 
     The obtained organic layer was washed one time with water, and dried with magnesium sulfate, filtered and concentrated. 
     The residue was crystalized with solution of ethylace tate/hexane/ethylether to afford 2.4 g of the desired product (white solid, yield: 80%) 
     M.P.: 176°-178° C. 
       1  H NMR (CDCl 3 ): δ2.03(s,3H), 3.93(s, 6H), 4.16-4.36(m, 1H), 4.90-5.10(m, 1H), 5.76(s, 1H), 6.40-6.95(m, 1H), 7.30-7.70(m, 4H), 8.15-8.40(m, 1H), 13.2(br s, 1H). 
     IR (KBr) ν(C═O) 1740 cm -1 , 1700 cm -1   
     EXAMPLE 5: N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1-hydroxy-2-fluoroethyl)benzenesulfonamide 
     2-(1-Acetoxy-2-fluoroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]benzenesulfonamide (2.4 g, 0.005 mmol) was dissolved in 80 ml of tetrahydrofuran, and herein lithium hydroxide monohydrate (0.7 g, 0.015 mol) and water were added. 
     After stirring for 12 hr at room temperature, the solution was diluted with 100 ml of water, and then conc-HCl was added dropwise at 0° C. to acidify the solution. The organic layer was obtained by adding 200 ml of methylene chloride, and the water layer was extracted two times with 100 ml of methylene chloride. 
     The combined organic layer was dried with magnesium sulfate, filtered and concentrated to obtain white solid. 
     This was washed with water and dried to afford 2.0 g of the desired product (white solid, yield: 93%) 
     M.P.: 180°-181° C. 
       1  H NMR (Acetone-d 6 ): δ3.98(s,6H), 4.29-4.67 (m, 2H), 5.88(s, 1H), 5.98(m, 1H), 4.22-8.19(m, 4H), 9.48(s, 1H), 5.25(s, 1H), 13.0(s, 1H). 
     IR (KBr) ν(C═O) 1700 cm -1   
     EXAMPLE 6: 2-(1-acetoxy-2-fluoroethyl)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide 
     2-(1-acetoxy-2-fluoroethyl)benzenesulfonamide (1.09 g, 0.004 mol) was dissolved in 20 ml of acetonitrile, and herein phenyl (4-methoxy-6-methylpyrimidin-2-yl)carbamate (1.06 g, 0.004 mol) was added at room temperature. 
     After adding dropwise 0.6 ml of DBU, the solution was stirred for 30 min, diluted with 80 ml of methylene chloride, and acidified with 5% hydrochloric acid. 
     The obtained organic layer was washed with water, and concentrated the residue was treated with solvent of ethyl acetate/hexane/ethylether to afford 1.4 g of the desired product (white solid, yield: 81%). 
     M.P.: 198°-200° C. 
       1  H NMR (DMSO-d 6 ): δ2.03(s, 3H), 2.40(s, 3H), 3.93(s, 3H), 4.10-4.50(m, 1H), 4.83-5.23(m, 1H), 6.26(s, 1H), 6.40-7.0(m, 1H), 7.26-7.73(m, 4H), 8.06-8.33(m, 1H), 9.13-9.46(m, 1H). 
     IR (KBr) ν(C═O) 1710 cm -1   
     EXAMPLE 7: 2(2-fluoro-1-hydroxyethyl)-N-[(4-methoxy-6-methyl pyrimidin-2-yl)aminocarbonyl]benzenesulfonamide 
     2-(1-Acetoxy-2-fluoroethyl)-N-[(4-methoxy-6-methoxylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide (1.4 g, 0.003 mol) was dissolved in 50 ml of tetrahydrofuran, and herein lithium hydroxide monohydride (0.4 g, 0.01 mol) and water were added. 
     After stirring for 12 hr at room temperature, the solution was diluted with 60 ml of water, and then conc-HCl was added dropwise at 0° C. to acidify the solution. The organic layer was obtained by adding 100 ml of methylene chloride, and the water layer was extracted with 60 ml of methylene chloride. The combined organic layer was dried, filtered and concentrated to obtain white solid. 
     This was washed with water and dried to afford 1.01 g of the desired product (white solid, yield: 89%). 
     M.P.: 153°-155° C. 
       1  H NMR (DMSO-d 6 ): δ2.40(s, 3H), 3.93(s, 3H), 400-4.40(m, 1H), 4.73-5.13(m, 1H), 5.40-610(m, 1H), 6.33(s, 1H), 7.33-8.26(m, 5H), 9.23-9.56(m, 1H). 
     IR (KBr) ν(C═O) 1710 cm -1   
     EXAMPLE 8: N-t-butyl-2(2-fluoro-1-hydroxy-n-propyl)benzenesulfonamide (8-A, 8-B) 
     10 g of N-t-butyl-2-(2-fluoropropionyl)benzenesulfonamide was dissolved in 100 ml of methanol, and herein 1.3 g of sodium borohydride was added in the solution at room temperature. 
     After stirring the solution for 30 min at 40° C., methanol was concentrated and the obtained residue was dissolved in 100 ml of methylene chloride, washed with 5% HCl solution. 
     The separated organic layer was dried, filtered and concentrated to obtain a residue of oil type. The residue was chromatographed through silical gel using 1:6 (v/v) of ethyl acetate/hexane as eluant, and then 3.5 g of nonpolar compound (8-A) and 6 g of polar compound (8-B) were obtained as the desired product. 
     [Compound 8-A] 
       1  H NMR (200 MHz, CDCl 3 ): δ1.24(s, 9H), 1.36(dd, 3H, J H-H  =6.4Hz, J H-F  =25.3Hz), 2.94(br s, 1H), 4.80-5.27(m, 2H), 5.66-5.77(m, 1H), 7.36-7.83(m, 3H), 8.03-8.10(m, 1H), 
     R f  =0.49 (ethyl acetate : hexane (v/v)=1:2) 
     [Compound 8-B] 
       1  H NMR (200MHz, CDCl 3 ): δ1.24(s, 9H), 1.36(dd, 3H, J H-H  =6.4Hz, J H-F  =25.3Hz), 3.01(br s, 1H), 4.83-5.25(m, 2H), 5.45-5.60(m, 1H), 7.35-7.70(m, 3H), 8.03-8.10(m, 1H). 
     R f  =0.42 (ethyl acetate : hexane (v/v)=1:2) 
     EXAMPLE 9: 2-(1-acetoxy-2-fluoro-n-propyl)-N-t-butyl benzenesulfonamide (9-A, 9-B) 
     Compound 8-A(3.5 g) according to the example 8 was dissolved in methylene chloride (50 ml), and herein acetic anhydride (1.25 ml), pyridine (1.1 ml) and N,N-dimethylaminopyridine (0.12 g) were added in the solution. 
     After stirring at room temperature for 24 hr, the reaction solution was washed with 5% HCl solution, and the separated organic layer was dried with magnesium sulfate, filtered and concentrated. 
     The obtained residue was chromatographed through the silica gel using 1:3 (v/v) of ethyl acetate/hexane to afford the desired compound 9-A (white solid, 3.7g). 
     [Compound 9-A] 
     M.P.: 134°-135° C. 
       1  H NMR (200MHz, CDCl 3 ): δ1.25(s, 9H), 1.36(dd, 3H, J H-H  =6.4Hz, J H-F  =25.3Hz), 2.17(s, 3H), 4.86-5.22(m, 1H), 5.47 (br s, 1H), 6.68 (dd, 1H, J H-H  =3Hz, J H-F  =18.6Hz), 7.41-7.71(m, 3H), 8.04-8.12(m, 1H) 
     IR (KBr) ν(C═O) 1715 cm -1   
     The desired compound 9-B (6.4 g) was obtained from the compound 8-B (6 g) according to the example 8 by the same process with the above. 
     [Compound 9-B] 
     M.P.: 126°-127° C. 
       1  H NMR (200MHz, CDCl 3 ): δ1.23(s, 9H), 1.36(dd, 3H, J H-H  =6.4Hz, J H-F  =23.6Hz), 2.18(s, 3H), 4.73-5.11(m, 1H), 5.54(br s, 1H), 6.49(dd, 1H, J H-H  =3.8Hz, J H-F  =21.6Hz), 7.41-7.69(m, 3H), 8.02-8.11(m, 1H) 
     IR (KBr) ν(C═O) 1715 cm -1   
     EXAMPLE 10: 2-(1-acetoxy-2-fluoro-n-propyl)benzenesulfonamide (10-A, 10-B) 
     Compound 9-A(3.7 g) according to the example 9 was dissolved in 20 ml of trifluoroacetic acid, and stirred at room temperature for 24 hr. 
     After concentrating under the reduced temperature, the residue was dissolved in 50 ml of methylene chloride, and the solution was washed one time with 20 ml of 5% NaHCO 3  solution. 
     The separated organic layer was dried with magnesium sulfate, filtered and concentrated, and the residue was chromatographed with ethyl acetate/hexane to afford the desired compound 10-A (white solid, 2.3 g). 
     [Compound 10-A] 
     M.P.: 105°-107° C. 
       1  H NMR (200MHz, CDCl 3 ): δ1.33(dd, 3H, J H-H  =6.4Hz, J H-F  =24.6Hz), 2.18(s, 3H), 4.85-5.23(m, 1H), 5.55(br s, 2H), 6.53-6.68(m, 1H), 7.46-7.75(m, 3H), 8.06-8.13 (m, 1H) 
     3.9 g of the desired compound 10-B (white solid) was obtained from the compound 9-B (6.4 g) according to the example 9 by the same process with the above. 
     [Compound 10-B] 
     M.P.: 126°-128° C. 
       1  H NMR (200MHz, CDCl 3 ): δ1.36(dd, 3H, J H-H  =6.4Hz, J H-F  =24.2Hz), 2.18(s, 3H), 4.75-5.12(m, 1H), 5.57(br s, 2H), 6.38-6.53(m, 1H), 7.46-7.66(m, 3H), 8.06-8.13(m, 1H) 
     EXAMPLE 11: 2-(1-acetoxy-2-fluoro-n-propyl)-N-[(4.6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide(11-A, 11-B) 
     The compound 10-A (2.3 g) according to the example 10 was dissolved in 20 ml of acetonitrile, and herein 2.3 g of phenyl 4,6-dimethoxy-pyrimidin-2-yl carbamate was added at room temperature. 
     After adding dropwise 1 ml of DBU and stirring for 30 min, the reacted solution was diluted with 100 ml of methylene chloride, and was acidified with 50 ml of 5% HCl. 
     The separated organic layer was washed with 50 ml of water, and dried with magnesium sulfate, filtered and concentrated. 
     The residue was treated with ethyl acetate/hexane/ethyl ether to afford the desired compound 11-A (white solid, 2.9 g). 
     [Compound 11-A] 
     M.P.: 191°-193° C. 
       1  H NMR (200MHz, CDCl 3 ): δ1.33(dd, 3H, J H-H  =6.4Hz, J H-F  =24.6Hz), 2.04(s, 3H), 3.96(s, 6H), 4.86-5.25(m, 1H), 5.80(s, 1H), 6.70-6.82(m, 1H), 7.18-7.70(m, 4H), 8.30-8.40(m, 1H), 13.15(br s, 1H) 
     The desired compound 11-B (white solid, 5.3 g) was obtained from the compound 10-B (3.9 g) according to the example 10 by the same process with the above. 
     [Compound 11-B] 
     M.P.: 194°-196° C. 
       1  H NMR (200MHz, CDCl 3 ): δ1.33(dd, 3H, J H-H-  =6.4Hz, J H-F  =24.2Hz), 2.04(s, 3H), 3.96(s, 6H), 4.80-5.14(m, 1H), 5.80(s, 1H), 6.42-6.62(m, 1H), 7.23-7.70(m, 4H), 8.27-8.37(m, 1H), 12.95(br s, 1H) 
     EXAMPLE 12: N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-hydroxy-n-propyl)benzenesulfonamide (12-A, 12-B) 
     The compound 11-A (2.9 g) according to the example 11 was dissolved in 60 ml of tetrahydrofuran, and herein 0.9 g of lithium hydroxide monohydrate and 10  ml of water were added. 
     After stirring at room temperature for 12 hr, the reacted solution was diluted with 10 ml of water, and was acidified by dropwise addition of conc-HCl at 0° C. 
     The reaction mixture was extracted with 1.00 ml of ethyl acetate, and then water layer was extracted one more time. 
     The combined organic layer was dried with magnesium sulfate, filtered and concentrated to obtain white solid. 
     This was washed with ethylether to afford the desired compound 12-A (2.3 g). 
     [Compound 12-A] 
     M.P.: 166°-168° C. 
       1  H NMR (200MHz, CDCl 3 ): δ1.33(dd, 3H, J H-H  =6.4Hz, J H-F  =24.6Hz), 3.08(br s, 1H), 3.96(s, 6H), 4.86-5.25(m, 1H), 5.80(s, 1H), 5.89-6.07(m, 1H), 7.36-8.24(m, 5H), 12.82(br s 1H) 
     IR (KBr) ν(C═O) 1692 cm -1   
     The desired compound 12-B (white solid, 3.0 g) was obtained from the compound 11-B (3.7 g) according to the example 11 by the same process with the above. 
     [Compound 12-B] 
     M.P.: 189°-191° C. 
       1  H NMR (200MHz, CDCl 3 ): δ1.36(dd, 3H, J H-H  =6.4Hz, J H-F  =24.2Hz), 3.96(s, 6H), 4.78-5.11(m, 1H), 5.80(s, 1H), 5.79-5.91(m, 1H), 7.22-7.78(m, 4H), 8.13-8.22(m, 1H), 12.75(br s, 1H) 
     IR (KBr) ν(C═O) 1691 cm -1   
     EXAMPLE 13 
     
         ______________________________________Wettable Powder______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                       80%(2-fluoro-1-hydroxyethyl)benzenesulfonamidesodium alkylnaphthalenesulfonate                        2%sodium lignisulfonate        2%synthetic amorphous silica   3%kaolinite                   13%______________________________________ 
    
     The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged. 
     EXAMPLE 14 
     
         ______________________________________Wettable Powder______________________________________2-(2-fluoro-1-hydroxyethyl)-N-[(4-methoxy-6-methyl-                      50%pyrimidin-2-yl)amino carbonyl]benzenesulfonamidesodium alkylnaphthalenesulfonate                       2%low viscosity methyl cellulose                       2%diatomaceous earth         46%______________________________________ 
    
     The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging. 
     EXAMPLE 15 
     
         ______________________________________Granule______________________________________wettable powder of Example 14                         5%attapulgite granules (U.S.S. 20-40 mesh; 0.84˜0.42                        95%______________________________________ 
    
     A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. 
     The granules are dried and packaged. 
     EXAMPLE 16 
     
         ______________________________________Extruded Pellet______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                       25%(2-fluoro-1-hydroxyethyl)benzenesulfonamideanhydrous sodium sulfate    10%crude calcium lignisulfonate                        5%sodium alkylnaphthalenesulfonate                        1%calcium/magnesium bentonite 59%______________________________________ 
    
     The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. They may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled. 
     EXAMPLE 17 
     
         ______________________________________Oil Suspension______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                       25%(2-fluoro-1-hydroxyethyl)benzenesulfonamidepolyoxyethylene sorbitol hexaoleate                        5%highly aliphatic hydrocarbon oil                       70%______________________________________ 
    
     The ingredients are ground together in sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. 
     EXAMPLE 18 
     
         ______________________________________Wetting Powder______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                       20%(2-fluoro-1-hydroxyethyl)benzenesulfonamidesodium alkylnaphthalenesulfonate                        4%sodium ligninsulfonate       4%low viscosity methyl cellulose                        3%attapulgite                 69%______________________________________ 
    
     The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm openings) and packaged. 
     EXAMPLE 19 
     
         ______________________________________Low Strength Granule______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                        1%(2-fluoro-1-hydroxyethyl)benzenesulfonamideN,N-dimethylformamide        9%attapulgite granule (U.S.S. 20-40 sieve)                       90%______________________________________ 
    
     The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. 
     After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. 
     EXAMPLE 20 
     
         ______________________________________Aqueous Suspension______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                      40%(2-fluoro-1-hydroxyethyl)benzenesulfonamidepolyacrylic acid thickener                     0.3%dodecylphenol polyethylen glycol ether                     0.5%disodium phosphite          1%monosodium phosphate      0.5%polyvinyl alcohol           1%water                     56.7%______________________________________ 
    
     The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size. 
     EXAMPLE 21 
     
         ______________________________________Solution______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                        5%(2-fluoro-1-hydroxyethyl)benzenesulfonamidewater                       95%______________________________________ 
    
     The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use. 
     EXAMPLE 22 
     
         ______________________________________Low Strength Granule______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                      0.1%(2-fluoro-1-hydroxyethyl)benzenesulfonamideattapulgite granules (U.S.S. No. 20-40 mesh)                     99.9%______________________________________ 
    
     The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and packaged. 
     EXAMPLE 23 
     
         ______________________________________Wettable Powder______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                       40%(2-fluoro-1-hydroxyethyl)benzenessulfonamidedioctyl sodium sulfosuccinate                       1.5%sodium ligninsulfonate       3%low viscosity methyl cellulose                       1.5%attapulgite                 54%______________________________________ 
    
     The ingredient are throughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging. All compounds of the invention may be formulated in the same manner. 
     EXAMPLE 24 
     
         ______________________________________Granule______________________________________wettable powder of Example 23                 15%gypsum                69%potassium sulfite     16%______________________________________ 
    
     The ingredients are blended in rotating mixer and water sprayed on to accomplished granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S. #. 18 to 40 sieves), the granules are removed, dried, and screened. Over said material is crushed additional material in the desired range. These granules contain % active ingredient. 
     EXAMPLE 25 
     
         ______________________________________High Strength Concentrate______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                        99%(2-fluoro-1-hydroxyethyl)benzenesulfonamidesilica aerogel              0.5%synthetic amorphous silica  0.5%______________________________________ 
    
     The ingredient are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary. 
     EXAMPLE 26 
     
         ______________________________________Wettable Powder______________________________________N-[(4,6-dlmethoxypyrimidin-2-yl)aminocarbonyl]-2-                        90%(2-fluoro-1-hydroxyethyl)benzenesulfonamidedioctyl sodium sulfosuccinate                       0.1%synthetic fine silica       9.9%______________________________________ 
    
     The ingredient are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and the packaged. 
     EXAMPLE 27 
     
         ______________________________________Wettable Powder______________________________________N-[(4,6-dlmethoxypyrimidln-2-yl)aminocarbonyl]-2-                       40%(2-fluoro-1-hydroxyethyl)benzenesulfonamidesodium ligninsulfonate      20%montmorillonite clay        40%______________________________________ 
    
     The ingredients are throughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and the packaged. 
     EXAMPLE 28 
     
         ______________________________________Oil Suspension______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                       35%(2-fluoro-1-hydroxyethyl)benzenesulfonamideblended of polyalcohol carboxylic ester and oil                        6%soluble petroleum sulfonatexylene                      59%______________________________________ 
    
     The ingredients are combined and ground together in a sand mill to produce particle essentially all below 5 microns. The product can be used directly, extended with oil, or emulsified in water. 
     EXAMPLE 29 
     
         ______________________________________Dust______________________________________N[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                       10%(2-fluoro-1-hydroxyethyl)benzenesulfonamideattapulgite                 10%pyrophyllite                80%______________________________________ 
    
     The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. 
     EXAMPLE 30 
     
         ______________________________________Emulsifiable Concentrate______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                       10%(2-fluoro-1-hydroxyethyl)benzenesulfonamidechlorobenzene               84%sorbitan monostearate and polyoxyethylenecondensates thereof          6%______________________________________ 
    
     The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. 
     EXAMPLE 31 
     Pre-emergence test 
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with 5 parts by weight of acetone, 1 part by weight of alkylaryl polyglycol ether of emulsifier is added and the concentrate is diluted with water to the desired concentration. 
     Seeds of the test plants are shown in normal soil and, after 24 hours, watered with the preparation of the active compound. 
     It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being desicive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. 
     The figures denote: 
     0%=no action (like untreated control) 
     20%=slight effect 
     70%=herbicidal effect 
     100%=total destruction. 
     In this test, the active compounds(I) according to the preparation Examples exhibit a better herbicidal activity against nomo- and dicotyledon weeds. 
     EXAMPLE 32 
     Post-emergence test 
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with 5 parts by weight of acetone, 1 parts by weight of alkylaryl polyglycol ether of emulsifier is added and the concentrate is diluted with water to the desired concentration. 
     Test plants which have a height of 5˜15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 2,000 l of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparasion to the development of the untreated control. 
     The figures denote: 
     0%=no action (like untreated control) 
     20%=slight effect 
     70%=herbicidal effect 
     100%=total destruction. 
     In this test, the active compounds(I) according to the preparation Examples exhibit a better herbicidal activity against mono- and dicotyledon weeds. 
     It is understood that the specification and examples are illustrative but not limitative of the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skilled in the art. 
     The herbicidal proficiency of the active ingredients of the present invention is evident from the test results which are recorded in following Tables. 
     The following Tables are represented pre- and post-emergence herbicidal evaluation [PRIMARY SCREENING (Herbicide)] of following &#34;Test compounds&#34;. 
     
         __________________________________________________________________________Structure            X   Y   Compound No.__________________________________________________________________________ ##STR31##                 ##STR32##                     ##STR33##                         ##STR34## ##STR35##                 ##STR36##                     ##STR37##                         ##STR38## ##STR39##                 ##STR40##                     ##STR41##                         ##STR42## ##STR43##                 ##STR44##                     ##STR45##                         ##STR46## ##STR47##                 ##STR48##                     ##STR49##                         ##STR50## ##STR51##                 ##STR52##                     ##STR53##                         ##STR54## ##STR55##           OCH.sub.3                    OCH.sub.3                        15__________________________________________________________________________ 
    
     
         __________________________________________________________________________PLANT RESPONSE SCREENING (Herbicide)                 BROJAComp.                 (SETVI)No. TYPE kg/ha        SORBI            ECHOR                 [AGRSM]                       DIGSA                            PANDI                                 SOLNI                                      AESIN                                           ABUTH                                                XANSI                                                     CAGHE__________________________________________________________________________1   PRE  .05 100 100  90    100  100  65   90   90   90   100    POST .05 100 100  100   100  100  70   100  100  100  1002   PRE  .05 100 100  100   100  100  50   100  90   100  100    POST .05 100 100  100   100  100  20   100  80   100  1003   PRE  .05 100 100  90    65   100  60   25   40   35   90    POST .05 100 100  100   55   100  60   90   20   100  904   PRE  .05 100 100  [15]  100  100  50   80   90   90   100    POST .05 90  100  [50]  100  100  50   100  70   100  1005   PRE  2   100 100  [100] 100  100  90   100  85   100  100    POST 2   100 100  [95]  100  100  100  100  100  100  1006   PRE  .05 100 100  [25]  100  100  65   60   40        100    POST .05 90  90   [50]  90   100  15   90   25   90   1007   PRE  .05 100 100  [60]  100  100  60   80   90   90   100    POST .05 100 100  [65]  100  100  50   100  100  100  1008   PRE  .05 100 100  [80]  100  100  60   90   90        100    POST .05 65  90   [65]  100  100  25   100  45   100  1009   PRE  .05 100 90   [20]  60   100  65   90   60        100    POST .05 70  80   [30]  25   75   20   100  35   100  10010  PRE  .05 0   0    [0]   0    0    0    0    0    0    0    POST .05 0   0    [0]   0    0    0    0    0    0    011  PRE  4   80  80   [40]  90   90   50   0    50   60   70    POST 4   50  90   [40]  60   70   45   30   80   60   10013  PRE  .05 100 90   (60)  100  100       80   90   80   100    POST .05 70  100  (70)  60   100       100  100  100  8014  PRE  .05 100 100  (80)  100  100       70   90   85   100    POST .05 60  80   (60)  50   100       80   40   70   10015  PRE  .05 50  50   0     20        20   0    0    0    30    POST .05 40  60   0     20   100  60   20   0    20   40__________________________________________________________________________ 
    
     
           PRIMARY SCREENING (Herbicide)           BROJA                  (SETVI) Comp. No. TYPE kg/ha ZEAMX GLXMX GOSHI TRZAW ORYSA SORBI ECHOR [AGRSM] DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE   1 PRE .1 100 100 100 50 100 100 100 (100) 100 100 50 100 100 100 100 .05 100 100 100 20 100 100 100 (100) 100 100 40 70 100 90 100   .025 100 100 100 10 100 100 100 (100) 100 100 20 40 90 90 100   .0125 65 90 80 0 100 100 100 (100) 100 100 0 20 60 80 100   .006 40 65 60 0 90 100 100 (90) 100 100 0 0 30 70 100  POST .1 100 100 100 40 100 100 100 (100) 100 100 40 100 100 100 100   .05 100 100 60 30 100 100 100 (100) 100 100 30 100 100 100 100   .025 70 100 40 0 70 100 100 (100) 100 100 30 100 100 100 100   .0125 60 100 0 0 60 100 100 (100) 80 100 0 70 70 70 100   .006 40 100 0 0 40 100 100 (30) 20 100 0 70 50 20 100 2 PRE 1  100 90 100 100 100 100 100 100 100 90 80 100 100 100   .05  100 90 90 100 100 100 100 100 100 60 80 100 100 100   .025  90 90 60 100 100 100 100 100 100 50 65 90 100 100   .012  80 80 40 100 100 100 90 100 100 50 40 80 90 100 .006  80 70 20 100 90 100 70 100 100 50 30 70 80 100  POST .1 100 100 80 100 100 100 100 100 100 100 70 100 100 100 100   .05 100 100 80 100 100 80 100 100 100 100 70 100 100 100 100   .025 100 90 75 40 100 80 100 100 100 100 60 100 65 100 100   .012 100 90 60 30 100 80 100 100 90 100 50 100 50 100 100   .006 100 90 60 20 100 80 100 100 80 100 50 80 50 100 100 3 PRE .1 100 50 50 40 100 100 100 (100) 100 100 90 30 40 60 100 .05 100 40 40 30 100 100 100 (50) 100 100 50 0 30 40 100   .025 40 30 0 10 100 100 100 (30) 80 90 0 0 20 20 100   .0125 0 0 0 0 50 100 40 (0) 40 70 0 0 0 0 50   .006 0 0 0 0 30 90 0 (0) 0 0 0 0 0 0 40  POST .1 80 60 70 60 100 100 100 (100) 100 100 50 70 60 70 100   .05 60 40 50 40 100 100 100 (50) 30 80 50 60 20 50 100   .025 40 30 30 30 90 40 40 (20) 0 30 30 40 0 0 100   .0125 0 29 0 0 80 0 20 (0) 0 0 20 0 0 0 100   .006 0 20 0 0 60 0 0 (0) 0 0 0 0 0 0 100 4 PRE 1 100 90 100 0 100 100 100 [60] 100 100 90 60 100 100 100   .025 50 50 40 0 40 100 80 [30] 80 100 50 20 50 65 100   .00625 20 20 0 0 0 50 40 [0] 30 80 0 0 0 30 90   .001562 0 0 0 0 0 0 0 [0] 0 30 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST .1 70 100 60 30 50 100 100 [40] 100 100 90 100 100 100 100   .025 50 100 30 0 30 100 60 [20] 40 100 40 90 40 90 30   .00625 30 70 0 0 0 70 0 [0] 30 70 30 40 0 40 30   .001562 0 40 0 0 0 0 0 [0] 0 20 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 5 PRE .1 100 100 100 20 100 100 100 [70] 100 100 70 90 90 100 100   .025 100 90 100 0 100 100 100 (60) 100 100 60 30 65 100 100   .00625 50 70 50 0 50 100 100 [40] 100 100 60 0 40 90 80  .00156 0 20 0 0 0 50 50 [0] 60 100 40 0 0 70 50   .00039 0 0 0 0 0 0 0 [0] 40 100 0 0 0 40 0  POST .1 100 100 90 40 50 100 100 [70] 100 100 100 100 100 100 100   .025 100 100 40 0 30 100 100 [50] 100 100 60 60 100 100 100   .00625 90 90 20 0 10 70 100 [20] 60 100 50 50 40 100 90 .00156 20 50 0 0 0 50 50 [0] 0 80 50 20 0 80 40   .00039 0 40 0 0 0 0 0 [0] 0 20 40 0 0 30 0 7 PRE .1 100 100 100 30 100 100 100 [80] 100 100 70 100 100 100 100   .025 50 80 100 0 100 100 100 [65] 100 100 70 40 80 100 100   .00625 40 50 40 0 90 100 70 [30] 70 100 40 0 30 50 50   .001562 0 20 0 0 60 30 0 [0] 30 30 30 0 0 0 20   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST .1 90 100 60 40 100 100 100 [100] 100 100 80 100 100 100 100   .025 50 100 40 0 100 100 100 [60] 100 100 60 100 40 100 100   .00625 0 80 0 0 60 80 80 [30] 40 100 50 60 30 60 40   .001562 0 60 0 0 20 80 20 [0] 0 60 30 0 0 40 30   .00039 0 20 0 0 0 40 0 [0] 0 50 0 0 0 0 0 8 PRE .1 100 100 100 90 100 100 100 [80] 100 100 90 100 100 100 100   .025 100 100 100 50 100 100 100 [80] 100 100 90 100 100 100 100   .00625 70 70 100 30 100 80 90 [50] 100 90 70 80 60 100 100   .001562 0 40 40 0 50 60 50 [30] 40 50 40 20 40 40 100   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 40 POST .1 100 100 90 60 100 100 100 [70] 100 100 80 100 70 100 100   .025 70 100 70 40 100 100 100 [50] 100 100 60 90 0 100 90   .00625 40 90 50 30 60 50 60 [20] 40 20 50 50 0 80 40   .001562 0 40 0 0 30 20 30 [0] 20 0 40 0 0 20 20   .00039 0 20 0 0 0 0 0 [0] 0 0 0 0 0 0 0 13  PRE .1 90 90 100 0 100 100 100 (70) 100 100 50 40 90 100 100   .025 90 65 65 0 90 80 80 (60) 90 100 30 20 70 100 100   .00625 20 20 50 0 40 40 65 (20) 60 80 0 0 0 40 40   .00156 0 0 50 0 0 0 0 (0) 20 60 0 0 0 0 0  POST .1 80 100 60 0 80 100 100 (65) 90 100 40 100 100 100 70   .025 70 80 40 0 50 50 80 (30) 40 100 0 80 100 100 60   .00625 30 40 40 0 30 50 40 (0) 0 80 0 40 40 50 0   .00156 0 40 20 0 0 40 0 (0) 0 0 0 0 0 20 0 14  PRE .1 90 100 100 30 100 100 100 (70) 100 100 50 60 90 100 100   .025 50 65 90 0 90 50 90 (50) 90 90 30 30 40 100 100   .00625 0 20 60 0 40 30 65 (20) 70 70 0 0 0 40 100   .00156 0 0 40 0 0 0 50 (0) 50 70 0 0 0 0 40  POST .1 90 70 65 0 90 40 80 (60) 50 70 40 80 70 100 100   .025 30 50 20 0 40 20 40 (0) 20 20 0 50 40 20 60   .00625 0 20 0 0 0 0 0 (0) 0 0 0 0 0 0 20 .00156 0 0 0 0 0 0 0 (0) 0 0 0 0 0 0 0 
    
     
         __________________________________________________________________________PRIMARY SCREENING (PADDY SUBMERGED) - Herbicide         ORYSA              ORYSAComp. No. DAT kg/ha         (3 Leaf)              (seed)                   ECHOR                        SCPJU                            MOOVA                                 CYPSE                                      SAGPY__________________________________________________________________________1     2   .05 90   90   100  100 100  100  1002     2   .05 90   90   80   100 100  100  70     .1  90   100  100  100 100  100  90     .025         90   90   90   100 90   100  80     .006         70   60   60   100 80   100  70     .0015         20   10   0    50  70   50   40     .0004         0    0    0    0   60   0    03     2   .05 70   60   60   50  70   60   604     2   .05 60   70   90   90  90   100  90     .05 60   90   100  100 100  100  100     .025         50   50   90   90  100  100  100     .0125         40   50   70   70  100  100  100     .006         30   20   30   30  100  100  100     .003         0    0    0    0   100  100  100     .005         0    30   0    90  0    100  100     .0025         0    0    0    40  0    90   90     .00125         0    0    0    0   0    50   70     .00063         0    0    0    0   0    30   50     .00031         0    0    0    0   0    0    05     3   .01 0    80   100      100  100  100     .005         0    50   100      90   100  100     .0025         0    0    90       90   100  100     .0012         0    0    70       80   70   100     .00062         0    0    20       70   40   956     2   .05 60   60   60   80  40   100  807     2   .05 90   100  100  100 100  100  100     .05 100  100  100  100 100  100  100     .025         90   100  100  90  100  100  100     .0125         80   90   100  80  100  100  100     .006         80   80   40   70  100  100  100     .003         50   50   20   30  100  100  100 3   .05 90   100  100  95  95   100  100     .0125         30   10   30   30  60   95   100     .003         0    0    0    0   0    0    60     .00078         0    0    0    0   0    0    0     .0002         0    0    0    0   0    0    08     2   .05 70   90   90   90  90   100  90     .05 80   90   100  80  100  100  100     .025         80   80   100  80  100  100  100     .0125         70   60   40   30  100  60   100     .006         40   40   30   0   90   60   90     .003         20   20   0    0   90   30   709     2   .05 70   90   90   90  90   100  90     .05 60   70   90   70  100  100  100     .025         50   60   70   30  100  100  100     .0125         30   40   40   0   100  100  100     .006         30   20   0    0   80   100  100     .003         20   0    0    0   50   80   8010    2   .05 0    0    0    0   0    0    011    2   .05 0    0    50   0   0    20   012    2   .05 10   10   40   40  40   60   6013    2   .05 60   60   90   70  80   30   90 3   .1  100  90   100  100 100  100  100     .025         70   70   100  100 100  50   90     .006         40   40   80   40  60   0    90     .0015         10   0    40   0   30   0    80     .0004         0    0    20   0   0    0    014    2   .05 50   60   70   50       90   80 3   .1  70   90   100  90  100  100  90     .025         40   50   90   50  60   60   90     .006         0    30   30   20  0    30   40     .0015         0    0    0    0   0    0    0     .0004         0    0    0    0   0    0    015    2   .05 40   50   0    0   50   0    60__________________________________________________________________________