Pyrazolesulfonylurea derivatives, preparation thereof, herbicide containing said derivative as active ingredient and herbicidal method by use thereof

This invention relates to a novel pyrazolesulfonylurea derivative represented by the formula (I), preparation thereof, a herbicide containing said derivative as an active ingredient and a herbicidal method by use thereof. ##STR2## wherein A represents a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group or a phenyl group which may be substituted with C.sub.1 -C.sub.8 alkyl groups, halogen atoms or nitro groups; B and C represent independently hydrogen atoms, halogen atoms, nitro groups, C.sub.1 -C.sub.8 alkyl groups, arylalkyl groups, C.sub.1 -C.sub.8 alkoxy groups, haloalkyl groups, --CO.sub.2 R (where R is a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group, an allyl group or a propargyl group), --CONR.sub.1 R.sub.2 [where R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group or a phenyl group, R.sub.2 is a hydrogen atom or a C.sub.1 -C.sub.8 alkyl group, or R.sub.1 and R.sub.2 taken together may represent --(CH.sub.2).sub.m -- (m is 4, 5 or 6), --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 --], --S(O).sub.n R.sub. 3 (where R.sub.3 is a C.sub.1 -C.sub.8 alkyl group, a phenyl group or an arylalkyl group and n is 0, 1 or 2), --SO.sub.2 NR.sub.4 R.sub.5 [where R.sub.4 is a C.sub.1 -C.sub.8 alkyl group, R.sub.5 is a hydrogen atom or a C.sub.1 -C.sub.8 alkyl group, or R.sub.4 and R.sub.5 taken together may represent --(CH.sub.2).sub.p -- (p is 4, 5 or 6), --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 --] or a phenyl group which may be substituted with C.sub.1 -C.sub.8 alkyl groups, halogen atoms or nitro groups; D represents a hydrogen atom or a C.sub.1 -C.sub.8 alkyl group; X and Y represent independently hydrogen atoms, halogen atoms, C.sub.1 -C.sub.8 alkyl groups, C.sub.1 -C.sub.8 alkoxy groups, C.sub.1 -C.sub.8 alkoxyalkyl groups, --CF.sub.3 groups, C.sub.1 -C.sub.8 haloalkoxy groups, alkylamino goups, dialkylamino groups, ##STR3## (where R.sub.6 and R.sub.7 each represent hydrogen atoms or C.sub.1 -C.sub.8 alkyl groups) or either X or Y may form a five-membered ring containing an oxygen atom together with Z; and Z represents a nitrogen atom or C-R.sub.8 (where R.sub.8 represents a hydrogen atom, a haloalkyl group or may form a five-membered ring containing an oxygen atom together with X or Y).
The compounds of this invention are novel compounds not disclosed in literatures and have excellent herbicidal activities.
Japanese Unexamined Patent Publication Nos. 102577/1980 and 139466/1981 disclose pyridinesulfonylurea derivatives and Japanese Unexamined Patent Publication No. 169688/1981 discloses pyrolesulfonylurea derivatives, respectively, as useful herbicides Heretofore, in using herbicides, it has been pointed out that the economical cost involved in the use of a herbicide depends on the application amount of the active ingredient per unit area. For this reason, studies have been continued for many years to obtain compounds which can exhibit high herbicidal effects at lower application rate.
In the prior art, as pyrazole derivatives, there have been known a large number of compounds, as disclosed in Japanese Patent Publication No. 36648/1979 and Japanese Unexamined Patent Publication Nos. 41872/1979, 2276/1982, 58670/1982 and 133265/1976.
The present inventors have made various investigations for many years and consequently found that the compounds of this invention have markedly high herbicidal effects as compared with the above pyrazole derivatives known in the art and are practically useful. On the other hand, as sulfonylurea derivatives containing a nitrogen-containing heterocyclic ring, the aforementioned pyrolesulfonylurea and pyridinesulfonylurea are known. As compared with these known compounds, the compounds of this invention have been found to exhibit markedly higher herbicidal effects. The present invention has been accomplished on the basis of these findings.
That is, the compounds of this invention may be said to be epoch-making herbicides capable of decreasing markedly the amount of the active ingredient applied per unit area as compared with these compounds known in the art, having a very great economical effect as compared with the herbicides of the prior art, and also capable of alleviating markedly the environmental pollution which may be caused by application of a large amount of pesticides.
Typical examples of the derivatives represented by the above formula (I) suitable for use as herbicides may include those as shown in Table 1, Table 2 and Table 3 set forth below.
The Compounds Nos. in these Tables are referred to in the following description.
TABLE 1__________________________________________________________________________ ##STR4##Comp.No. A B C X Y Z__________________________________________________________________________1 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH3 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH4 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N5 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 N ##STR5## CH.sub.3 CH.sub.3 CH.sub.3 H CH7 ##STR6## CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH8 ##STR7## CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH9 ##STR8## CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH10 ##STR9## CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N11 ##STR10## CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 N12 CH.sub.3 ##STR11## CH.sub.3 CH.sub.3 CH.sub.3 CH13 CH.sub.3 ##STR12## CH.sub.3 CH.sub.3 OCH.sub.3 CH14 CH.sub.3 ##STR13## CH.sub.3 OCH.sub.3 OCH.sub.3 CH15 CH.sub.3 ##STR14## CH.sub.3 CH.sub.3 OCH.sub.3 N16 CH.sub.3 ##STR15## CH.sub.3 OCH.sub.3 OCH.sub.3 N17 CH.sub.3 ##STR16## CH.sub.3 CH.sub.3 CH.sub.3 N18 CH.sub.3 ##STR17## CH.sub.3 CH.sub.3 Cl CH19 CH.sub.3 ##STR18## CH.sub.3 CH.sub.3 Cl C(CH.sub.2).sub.2 Cl20 CH.sub.3 ##STR19## CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 C21 CH.sub.3 ##STR20## CH.sub.3 Cl N(CH.sub.3).sub.2 N22 CH.sub.3 ##STR21## CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 N23 CH.sub.3 ##STR22## CH.sub.3 CH.sub.3 CH.sub.3 CH24 CH.sub.3 ##STR23## CH.sub.3 CH.sub.3 OCH.sub.3 CH25 CH.sub.3 ##STR24## CH.sub.3 CH.sub.3 OCH.sub.3 N26 CH.sub.3 ##STR25## CH.sub.3 CH.sub.3 OCH.sub.3 CH27 CH.sub.3 ##STR26## CH.sub.3 CH.sub.3 OCH.sub.3 N28 CH.sub.3 ##STR27## CH.sub.3 CH.sub.3 CH.sub.3 CH29 CH.sub.3 ##STR28## CH.sub.3 CH.sub.3 OCH.sub.3 CH30 CH.sub.3 ##STR29## CH.sub.3 CH.sub.3 OCH.sub.3 N31 CH.sub.3 ##STR30## CH.sub.3 CH.sub.3 CH.sub.3 CH32 CH.sub.3 ##STR31## CH.sub.3 CH.sub.3 OCH.sub.3 CH33 CH.sub.3 ##STR32## CH.sub.3 CH.sub.3 OCH.sub.3 N34 CH.sub.3 ##STR33## CH.sub.3 CH.sub.3 OCH.sub.3 CH35 CH.sub.3 ##STR34## CH.sub.3 CH.sub.3 OCH.sub.3 N36 CH.sub.3 ##STR35## CH.sub.3 CH.sub.3 OCH.sub.3 CH37 CH.sub. 3 ##STR36## CH.sub.3 CH.sub.3 OCH.sub.3 N38 CH.sub.3 ##STR37## CH.sub.3 CH.sub.3 OCH.sub.3 CH39 CH.sub.3 ##STR38## CH.sub.3 CH.sub.3 OCH.sub.3 N40 CH.sub.3 ##STR39## H CH.sub.3 CH.sub.3 CH41 CH.sub.3 ##STR40## H CH.sub.3 OCH.sub.3 CH42 CH.sub.3 ##STR41## H CH.sub.3 OCH.sub.3 N43 CH.sub.3 CH.sub.3 ##STR42## CH.sub.3 CH.sub.3 CH44 CH.sub.3 CH.sub.3 ##STR43## CH.sub.3 OCH.sub.3 CH45 CH.sub.3 CH.sub.3 ##STR44## OCH.sub.3 OCH.sub.3 CH46 CH.sub.3 CH.sub.3 ##STR45## CH.sub.3 OCH.sub.3 N47 CH.sub.3 CH.sub.3 ##STR46## OCH.sub.3 OCH.sub.3 N48 H ##STR47## CH.sub.3 CH.sub.3 CH.sub.3 CH49 H ##STR48## CH.sub.3 CH.sub.3 OCH.sub.3 CH50 H ##STR49## CH.sub.3 CH.sub.3 OCH.sub.3 N51 CH.sub.2 CH.sub.3 ##STR50## CH.sub.3 CH.sub.3 CH.sub.3 CH52 CH.sub.2 CH.sub.3 ##STR51## CH.sub.3 CH.sub.3 OCH.sub.3 CH53 CH.sub.2 CH.sub.3 ##STR52## CH.sub.3 CH.sub.3 OCH.sub.3 N54 CH.sub.2 CH.sub.2 CH.sub.3 ##STR53## CH.sub.3 CH.sub.3 CH.sub.3 CH55 CH.sub.2 CH.sub.2 CH.sub.3 ##STR54## CH.sub.3 CH.sub.3 OCH.sub.3 CH56 CH.sub.2 CH.sub.2 CH.sub.3 ##STR55## CH.sub.3 CH.sub.3 OCH.sub.3 N57 ##STR56## ##STR57## CH.sub.3 CH.sub.3 CH.sub.3 CH58 ##STR58## ##STR59## CH.sub.3 CH.sub.3 OCH.sub.3 CH59 ##STR60## ##STR61## CH.sub.3 CH.sub.3 OCH.sub.3 N60 CH.sub.3 ##STR62## ##STR63## CH.sub.3 CH.sub.3 CH61 CH.sub.3 ##STR64## ##STR65## CH.sub.3 OCH.sub.3 CH62 CH.sub.3 ##STR66## ##STR67## CH.sub.3 OCH.sub.3 N63 H ##STR68## ##STR69## CH.sub.3 CH.sub.3 CH64 H ##STR70## ##STR71## CH.sub.3 OCH.sub.3 CH65 H ##STR72## ##STR73## CH.sub.3 OCH.sub.3 N66 CH.sub.3 ##STR74## OCH.sub.3 CH.sub.3 CH.sub.3 CH67 CH.sub.3 ##STR75## OCH.sub.3 CH.sub.3 OCH.sub.3 CH68 CH.sub.3 ##STR76## OCH.sub.3 OCH.sub.3 OCH.sub.3 CH69 CH.sub.3 ##STR77## OCH.sub.3 OCH.sub.2 CH.sub.3 OCH.sub.2 CH.sub.3 CH70 CH.sub.3 ##STR78## OCH.sub.3 CH.sub.3 OCH.sub.3 N71 CH.sub.3 ##STR79## OCH.sub.3 OCH.sub.3 OCH.sub.3 N72 CH.sub.3 ##STR80## OCH.sub.3 CH.sub.3 CH.sub.3 N73 CH.sub.3 ##STR81## OCH.sub.3 CH.sub.3 Cl C(CH.sub.2).sub.2 Cl74 CH.sub.3 ##STR82## OCH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 C75 CH.sub.3 ##STR83## OCH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 N76 CH.sub.3 ##STR84## OCH.sub.3 CH.sub.3 CH.sub.3 CH77 CH.sub.3 ##STR85## OCH.sub.3 CH.sub.3 OCH.sub.3 CH78 CH.sub.3 ##STR86## OCH.sub.3 CH.sub.3 OCH.sub.3 N79 CH.sub.3 ##STR87## OCH.sub.3 CH.sub.3 CH.sub.3 CH80 CH.sub.3 ##STR88## OCH.sub.3 CH.sub.3 OCH.sub.3 CH81 CH.sub.3 ##STR89## OCH.sub.3 CH.sub.3 OCH.sub.3 N82 CH.sub.3 ##STR90## OCH.sub.3 CH.sub.3 CH.sub.3 CH83 CH.sub.3 ##STR91## OCH.sub.3 CH.sub.3 OCH.sub.3 CH84 CH.sub.3 ##STR92## OCH.sub.3 CH.sub.3 OCH.sub.3 N85 CH.sub.3 CH.sub.3 Cl CH.sub.3 CH.sub.3 CH86 CH.sub.3 CH.sub.3 Cl CH.sub.3 OCH.sub.3 CH87 CH.sub.3 CH.sub.3 Cl OCH.sub.3 OCH.sub.3 CH88 CH.sub.3 CH.sub.3 Cl CH.sub.3 OCH.sub.3 N89 CH.sub.3 CH.sub.3 Cl OCH.sub.3 OCH.sub.3 N90 CH.sub.3 CH.sub.3 Cl CH.sub.3 CH.sub.3 N91 CH.sub.3 CH.sub.3 Cl CH.sub.3 Cl C(CH.sub.2).sub.2 Cl92 CH.sub.3 CH.sub.3 Cl CH.sub.3 OCH.sub.2 CH.sub.2 C93 CH.sub.3 CH.sub.3 Cl OCH.sub.3 N(CH.sub.3).sub.2 N94 CH.sub.3 CH.sub.3 Cl CH.sub.2 CH.sub.3 OCH.sub.3 CH95 CH.sub.3 CH.sub.3 Cl CH.sub.3 CH.sub.2 OCH.sub.3 CH96 CH.sub.3 CH.sub.3 Cl CH.sub.3 OCH.sub.2 CO.sub.2 CH.sub.3 CH97 CH.sub.3 ##STR93## Cl CH.sub.3 CH.sub.3 CH98 CH.sub.3 ##STR94## Cl CH.sub.3 OCH.sub.3 CH99 CH.sub.3 ##STR95## Cl OCH.sub.3 OCH.sub.3 CH100 CH.sub.3 ##STR96## Cl CH.sub.3 OCH.sub.3 N101 CH.sub.3 ##STR97## Cl OCH.sub.3 OCH.sub.3 N102 CH.sub.3 ##STR98## Cl CH.sub.3 CH.sub.3 CH103 CH.sub.3 ##STR99## Cl CH.sub.3 OCH.sub.3 CH104 CH.sub.3 ##STR100## Cl CH.sub.3 OCH.sub.3 N105 CH.sub.3 CH.sub.3 Br CH.sub.3 CH.sub.3 CH106 CH.sub.3 CH.sub.3 Br CH.sub.3 OCH.sub.3 CH107 CH.sub.3 CH.sub.3 Br OCH.sub.3 OCH.sub.3 CH108 CH.sub.3 CH.sub.3 Br CH.sub.3 OCH.sub.3 N109 CH.sub.3 CH.sub.3 Br OCH.sub.3 OCH.sub.3 N110 CH.sub.3 H Cl CH.sub.3 CH.sub.3 CH111 CH.sub.3 H Cl CH.sub.3 OCH.sub.3 CH112 CH.sub.3 H Cl OCH.sub.3 OCH.sub.3 CH113 CH.sub.3 H Cl CH.sub.3 OCH.sub.3 N114 CH.sub.3 H Cl OCH.sub.3 OCH.sub.3 N115 CH.sub.3 CH.sub.2 CH.sub.3 Cl CH.sub.3 CH.sub.3 CH116 CH.sub.3 CH.sub.2 CH.sub.3 Cl CH.sub.3 OCH.sub.3 CH117 CH.sub.3 CH.sub.2 CH.sub.3 Cl CH.sub.3 OCH.sub.3 N118 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 Cl CH.sub.3 CH.sub.3 CH119 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 Cl CH.sub.3 OCH.sub.3 CH120 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 Cl CH.sub.3 OCH.sub.3 CH121 CH.sub.3 CH(CH.sub.3).sub.2 Cl CH.sub.3 CH.sub.3 CH122 CH.sub.3 CH(CH.sub.3).sub.2 Cl CH.sub.3 OCH.sub.3 CH123 CH.sub.3 CH(CH.sub.3).sub.2 Cl CH.sub.3 OCH.sub.3 CH124 H CH.sub.3 Cl CH.sub.3 CH.sub.3 CH125 H CH.sub.3 Cl CH.sub.3 OCH.sub.3 CH126 H CH.sub.3 Cl CH.sub.3 OCH.sub.3 N127 ##STR101## CH.sub.3 Cl CH.sub.3 CH.sub.3 CH128 ##STR102## CH.sub.3 Cl CH.sub.3 OCH.sub.3 CH129 ##STR103## CH.sub.3 Cl CH.sub.3 OCH.sub.3 N130 CH.sub.3 ##STR104## CH.sub.3 CH.sub.3 CH.sub.3 CH131 CH.sub.3 ##STR105## CH.sub.3 CH.sub.3 OCH.sub.3 CH132 CH.sub.3 ##STR106## CH.sub.3 OCH.sub.3 OCH.sub.3 CH133 CH.sub.3 ##STR107## CH.sub.3 CH.sub.3 OCH.sub.3 N134 CH.sub.3 ##STR108## CH.sub.3 OCH.sub.3 OCH.sub.3 N135 CH.sub.3 CH.sub.3 ##STR109## CH.sub.3 CH.sub.3 CH136 CH.sub.3 CH.sub.3 ##STR110## CH.sub.3 OCH.sub.3 CH137 CH.sub.3 CH.sub.3 ##STR111## CH.sub.3 OCH.sub.3 N138 CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH139 CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH140 CH.sub.3 CF.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH141 CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N142 CH.sub.3 CF.sub. 3 CH.sub.3 OCH.sub.3 OCH.sub.3 N143 CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 N144 CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 Cl N145 CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 Cl C(CH.sub.2).sub.2 Cl146 CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 C147 CH.sub.3 CF.sub.3 CH.sub.3 Cl N(CH.sub.3).sub.2 N148 CH.sub.3 CF.sub.3 CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 N149 CH.sub.3 CF.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3 NHCH.sub.3 N150 CH.sub.3 CF.sub.3 CH.sub.3 CH.sub.3 Cl CH151 CH.sub.3 CF.sub.3 CH.sub.3 Cl Cl CH152 H CF.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH153 H CF.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH154 H CF.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N155 ##STR112## CF.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH156 ##STR113## CF.sub.3 CH.sub.3 CH.sub. 3 OCH.sub.3 CH157 ##STR114## CF.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N158 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH159 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH160 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH161 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N162 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 N163 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 N164 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 Cl N165 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 Cl C(CH.sub.2).sub.2 Cl166 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 C167 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 Cl N(CH.sub.3).sub.2 N168 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 N169 CH.sub. 3 CO.sub.2 CH.sub.3 CH.sub.3 Cl CH.sub.3 CH170 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3 CH171 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3 N172 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 NHCH.sub.3 N173 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 H CH174 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 H H CH175 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 Cl Cl CH176 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH177 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH178 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH179 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N180 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 N181 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 N182 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 CH.sub.3 CH183 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 OCH.sub.3 CH184 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 OCH.sub.3 CH185 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 OCH.sub.3 N186 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 OCH.sub.3 N187 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 CH.sub.3 CH.sub.3 CH188 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 CH.sub.3 OCH.sub.3 CH189 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 OCH.sub.3 OCH.sub.3 CH190 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 CH.sub.3 OCH.sub.3 N191 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 OCH.sub.3 OCH.sub.3 N192 CH.sub.3 CO.sub.2 CH.sub.2 CHCH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH193 CH.sub.3 CO.sub.2 CH.sub.2 CHCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH194 CH.sub.3 CO.sub.2 CH.sub. 2 CHCH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH195 CH.sub.3 CO.sub.2 CH.sub.2 CHCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N196 CH.sub.3 CO.sub.2 CH.sub.2 CHCH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N197 CH.sub.3 CO.sub.2 CH.sub.2 CCH CH.sub.3 CH.sub.3 CH.sub.3 CH198 CH.sub.3 CO.sub.2 CH.sub.2 CCH CH.sub.3 CH.sub.3 CH.sub.3 CH -199 CH.sub.3 CO.sub.2 CH.sub.2 CCH CH.sub.3 CH.s ub.3 OCH.sub.3 N200 CH.sub.3 CO.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 CH201 CH.sub.3 CO.sub.2 H CH.sub.3 CH.sub.3 OCH.sub.3 CH202 CH.sub.3 CO.sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.3 CH203 CH.sub.3 CO.sub.2 H CH.sub.3 CH.sub.3 OCH.sub.3 N204 CH.sub.3 CO.sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.3 N205 H CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH206 H CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH207 H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH208 H CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N209 H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 N210 CH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH211 CH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH212 CH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N213 CH.sub.2 CH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH214 CH.sub.2 CH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH215 CH.sub.2 CH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N216 CH(CH.sub.3).sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH217 CH(CH.sub.3).sub.2 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH218 CH(CH.sub.3).sub.2 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N219 ##STR115## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH220 ##STR116## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH221 ##STR117## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH222 ##STR118## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N223 ##STR119## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 N224 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH225 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH226 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N227 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH228 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH229 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N230 CH.sub.3 CO.sub.2 CH.sub.3 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH231 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OCH.sub.3 CH246 CH.sub.3 CON(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N247 CH.sub.3 CON(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N248 CH.sub.3 ##STR120## CH.sub.3 CH.sub.3 CH.sub.3 CH249 CH.sub.3 ##STR121## CH.sub.3 CH.sub.3 OCH.sub.3 CH250 CH.sub.3 ##STR122## CH.sub.3 CH.sub.3 OCH.sub.3 N251 CH.sub.3 CONHCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH252 CH.sub.3 CONHCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH253 CH.sub.3 CONHCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N254 CH.sub.3 CONHC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 CH255 CH.sub.3 CONHC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 OCH.sub.3 CH256 CH.sub.3 CONHC.sub.2 H.sub.5 CH.sub. 3 CH.sub.3 OCH.sub.3 N257 CH.sub.3 ##STR123## CH.sub.3 CH.sub.3 CH.sub.3 CH258 CH.sub.3 ##STR124## CH.sub.3 CH.sub.3 OCH.sub.3 CH259 CH.sub.3 ##STR125## CH.sub.3 CH.sub.3 OCH.sub.3 N260 CH.sub.3 CO.sub.2 CH.sub.3 ##STR126## CH.sub.3 CH.sub.3 CH261 CH.sub.3 CO.sub.2 CH.sub.3 ##STR127## CH.sub.3 OCH.sub.3 CH262 CH.sub.3 CO.sub.2 CH.sub.3 ##STR128## OCH.sub.3 OCH.sub.3 CH263 CH.sub.3 CO.sub.2 CH.sub.3 ##STR129## CH.sub.3 OCH.sub.3 N264 CH.sub.3 CO.sub.2 CH.sub.3 ##STR130## OCH.sub.3 OCH.sub.3 N265 CH.sub.3 CO.sub.2 CH.sub.3 ##STR131## CH.sub.3 OCH.sub.3 CH266 CH.sub.3 CO.sub. 2 CH.sub.3 ##STR132## CH.sub.3 OCH.sub.3 N267 CH.sub.3 CO.sub.2 CH.sub.3 ##STR133## CH.sub.3 OCH.sub.3 CH268 CH.sub.3 CO.sub.2 CH.sub.3 ##STR134## CH.sub.3 OCH.sub.3 N269 CH.sub.3 CO.sub.2 CH.sub.3 ##STR135## CH.sub.3 OCH.sub.3 CH270 CH.sub.3 CO.sub.2 CH.sub.3 ##STR136## CH.sub.3 OCH.sub.3 N271 CH.sub.3 CO.sub.2 CH.sub.3 ##STR137## CH.sub.3 CH.sub.3 CH272 CH.sub.3 CO.sub.2 CH.sub.3 ##STR138## CH.sub.3 OCH.sub.3 CH273 CH.sub.3 CO.sub.2 CH.sub.3 ##STR139## CH.sub.3 OCH.sub.3 N274 CH.sub.3 CO.sub.2 CH.sub.3 ##STR140## CH.sub.3 CH.sub.3 CH275 CH.sub.3 CO.sub.2 CH.sub.3 ##STR141## CH.sub.3 OCH.sub.3 CH276 CH.sub.3 CO.sub.2 CH.sub.3 ##STR142## CH.sub.3 OCH.sub.3 N277 CH.sub.3 CO.sub.2 CH.sub.3 ##STR143## CH.sub.3 CH.sub.3 CH278 CH.sub.3 CO.sub.2 CH.sub.3 ##STR144## CH.sub.3 OCH.sub.3 CH279 CH.sub.3 CO.sub.2 CH.sub.3 ##STR145## CH.sub.3 OCH.sub.3 N280 H CO.sub.2 CH.sub.3 ##STR146## CH.sub.3 CH.sub.3 CH281 H CO.sub.2 CH.sub.3 ##STR147## CH.sub.3 OCH.sub.3 CH282 H CO.sub.2 CH.sub.3 ##STR148## CH.sub.3 OCH.sub.3 N283 CH.sub. 3 CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.3 CH284 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 CH285 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 CH286 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 N287 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 N288 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH289 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH290 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N291 CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.3 CH292 CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 CH293 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 CH294 CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 N295 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 N296 CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.3 N297 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 N(CH.sub.3).sub. N298 CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 CF.sub.3 CH299 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 ##STR149## CH300 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.2 CF.sub.3 N301 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH302 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH303 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N304 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 CH305 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CH306 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH307 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 N308 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 N309 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 N310 CH.sub.3 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH311 CH.sub.3 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH312 CH.sub.3 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N313 CH.sub.3 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH314 CH.sub.3 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH315 CH.sub.3 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N316 H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH317 H 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CH.sub.3 CH337 CH.sub.3 H C(CH.sub.3).sub.3 CH.sub.3 OCH.sub.3 CH338 CH.sub.3 H C(CH.sub.3).sub.3 CH.sub.3 OCH.sub.3 N339 H CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.3 CH340 H CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 CH341 H CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 N342 H CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 CH.sub.3 CH343 H CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 CH344 H CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 N345 H ##STR150## OCH.sub.3 CH.sub.3 CH.sub.3 CH346 H ##STR151## OCH.sub.3 CH.sub.3 OCH.sub.3 CH347 H ##STR152## OCH.sub.3 CH.sub.3 OCH.sub.3 N348 CH.sub.3 CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.3 CH349 CH.sub.3 CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 CH350 CH.sub.3 CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 CH351 CH.sub.3 CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 N352 CH.sub.3 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 N353 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.3 CH354 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 CH355 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 N356 CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 CH.sub.3 CH357 CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 CH358 CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub. 3 OCH.sub.3 OCH.sub.3 CH359 CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3 N360 CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 OCH.sub.3 N361 CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 Cl CH362 CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 CH363 CH.sub.3 CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 CH.sub.2 OCH.sub.3 N364 CH.sub.3 C(CH.sub.3).sub.3 OCH.sub.3 CH.sub.3 CH.sub.2 CH365 CH.sub.3 C(CH.sub.3).sub.3 OCH.sub.3 CH.sub.3 OCH.sub.2 CH366 CH.sub.3 C(CH.sub.3).sub.3 OCH.sub.3 CH.sub.3 OCH.sub.2 N367 CH.sub.3 SCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH368 CH.sub.3 SCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH369 CH.sub.3 SCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N370 CH.sub.3 S(O)CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH371 CH.sub.3 S(O)CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH372 CH.sub.3 S(O)CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N373 CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH374 CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH375 CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N376 CH.sub.3 SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH377 CH.sub.3 SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH378 CH.sub.3 SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N379 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 CH.sub.3 CH380 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 OCH.sub.3 CH381 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 OCH.sub.3 CH382 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 OCH.sub.3 N383 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 OCH.sub.3 N384 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH385 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH386 CH.sub. 3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH387 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N388 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N389 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 N390 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 Cl C(CH.sub.2).sub.2 Cl391 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 C392 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 Cl CH393 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3 CH394 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 H CH395 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.2 OCH.sub.3 CH396 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CF.sub.3 CH397 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.2 CF.sub.3 CH398 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub. 3 OCH.sub.2 CO.sub.2 CH.sub.3 CH399 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 Cl Cl CH400 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 Br Br CH401 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 Cl N402 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 Cl N(CH.sub.3).sub.2 N403 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 N404 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3 N405 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 NHCH.sub.2 CH.sub.3 N406 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.2 OCH.sub.3 N407 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 ##STR153## N408 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH409 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH410 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH411 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N412 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N413 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 Cl C(CH.sub.2).sub.2 Cl414 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 C415 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 CH416 CH.sub.3 CH.sub.3 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CH.sub.3 CH.sub.3 N508 CH.sub.3 ##STR171## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 C509 CH.sub.3 ##STR172## CO.sub.2 CH.sub.3 CH.sub.3 Cl C(CH.sub.2).sub.2 Cl510 CH.sub.3 ##STR173## CO.sub.2 CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 N511 CH.sub.3 ##STR174## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH512 CH.sub.3 ##STR175## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH513 CH.sub.3 ##STR176## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N514 CH.sub.3 ##STR177## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH515 CH.sub.3 ##STR178## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH516 CH.sub.3 ##STR179## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N517 CH.sub.3 ##STR180## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH518 CH.sub.3 ##STR181## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH519 CH.sub.3 ##STR182## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N520 CH.sub.3 ##STR183## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH521 CH.sub.3 ##STR184## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH522 CH.sub.3 ##STR185## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N523 CH.sub.3 ##STR186## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH524 CH.sub.3 ##STR187## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH525 CH.sub.3 ##STR188## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N526 CH.sub.3 ##STR189## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH527 CH.sub.3 ##STR190## CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH528 CH.sub.3 ##STR191## CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 N529 CH.sub.3 OCH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH530 CH.sub.3 OCH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH531 CH.sub.3 OCH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH532 CH.sub.3 OCH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N533 CH.sub.3 OCH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N534 CH.sub.3 OCH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 N535 CH.sub.3 OCH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH536 CH.sub.3 OCH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH537 CH.sub.3 OCH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N538 CH.sub.3 CH.sub.3 SCH.sub.3 CH.sub.3 CH.sub.3 CH539 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CH.sub.3 NHCH.sub.3 N584 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.2 CF.sub.3 N585 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 ##STR192## N586 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 CH.sub.3 CH587 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 CH.sub.3 CH588 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -i OCH.sub.3 CH.sub.3 CH589 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 OCH.sub.3 N590 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -i OCH.sub.3 OCH.sub.3 N591 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 CH.sub.3 N592 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 OCH.sub.2 CH.sub.2 C593 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 Cl C(CH.sub.2).sub.2 Cl594 CH.sub.3 CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -i OCH.sub.3 N(CH.sub.3).sub.2 N595 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH596 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH597 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CH598 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N599 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 N600 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N601 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.2 CH.sub.2 C601 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 Cl C(CH.sub.2).sub.2 Cl603 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 N(CH.sub.3).sub.2 N604 CH.sub.3 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3 CH605 CH.sub.3 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 CH606 CH.sub.3 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 OCH.sub.3 OCH.sub.3 CH607 CH.sub.3 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 N608 CH.sub.3 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 OCH.sub.3 OCH.sub.3 N609 CH.sub.3 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3 N610 CH.sub.3 CH.sub.3 ##STR193## CH.sub.3 CH.sub.3 CH611 CH.sub.3 CH.sub.3 ##STR194## CH.sub.3 OCH.sub.3 CH612 CH.sub.3 CH.sub.3 ##STR195## OCH.sub.3 OCH.sub.3 CH613 CH.sub.3 CH.sub.3 ##STR196## CH.sub.3 OCH.sub.3 N614 CH.sub.3 CH.sub.3 ##STR197## OCH.sub.3 OCH.sub.3 N615 CH.sub.3 CH.sub.3 ##STR198## CH.sub.3 CH.sub.3 N616 CH.sub.3 CH.sub.3 SO.sub.2 NHCH.sub.3 CH.sub.3 CH.sub.3 CH617 CH.sub.3 CH.sub.3 SO.sub.2 NHCH.sub.3 CH.sub.3 OCH.sub.3 CH618 CH.sub.3 CH.sub.3 SO.sub.2 NHCH.sub.3 CH.sub.3 OCH.sub.3 N619 CH.sub.3 CH.sub.3 SO.sub.2 NHC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH620 CH.sub.3 CH.sub.3 SO.sub.2 NHC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH621 CH.sub.3 CH.sub.3 SO.sub.2 NHC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N622 CH.sub.3 CH.sub.3 SO.sub.2 NHC.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 CH623 CH.sub.3 CH.sub.3 SO.sub.2 NHC.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 CH624 CH.sub.3 CH.sub.3 SO.sub.2 NHC.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 N625 CH.sub.3 H SCH.sub.3 CH.sub.3 OCH.sub.3 CH626 CH.sub.3 H SCH.sub.3 CH.sub.3 OCH.sub.3 N627 CH.sub.3 H S(O)CH.sub.3 CH.sub.3 CH.sub.3 CH628 CH.sub.3 H S(O)CH.sub.3 CH.sub.3 OCH.sub.3 CH629 CH.sub.3 H S(O)CH.sub.3 CH.sub.3 OCH.sub.3 N630 CH.sub.3 H SO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH631 CH.sub.3 H SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH632 CH.sub.3 H SO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH633 CH.sub.3 H SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N634 CH.sub.3 H SO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N635 CH.sub.3 H SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH636 CH.sub.3 H SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH637 CH.sub.3 H SO.sub.2 C.sub.2 H.sub.5 CH.sub. 3 OCH.sub.3 N638 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 CH639 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 CH640 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -n OCH.sub.3 OCH.sub.3 CH641 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 N642 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -n OCH.sub.3 OCH.sub.3 N643 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 N644 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.2 CH.sub.2 C645 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 Cl C(CH.sub.2).sub.2 Cl646 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -n OCH.sub.3 N(CH.sub.3).sub.2 N647 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 CH.sub.3 CH648 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 OCH.sub. 3 CH649 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -i OCH.sub.3 OCH.sub.3 CH650 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 OCH.sub.3 N651 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -i OCH.sub.3 OCH.sub.3 N652 CH.sub.3 H SO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 CH.sub.3 N653 CH.sub.3 H SO.sub.2 C.sub.4 H.sub.9 -n CH.sub.3 CH.sub.3 N654 CH.sub.3 H SO.sub.2 C.sub.4 H.sub.9 -n CH.sub.3 OCH.sub.3 CH655 CH.sub.3 H SO.sub.2 C.sub.4 H.sub.9 -n CH.sub.3 OCH.sub.3 N656 CH.sub.3 H SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH657 CH.sub.3 H SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH658 CH.sub.3 H SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CH659 CH.sub.3 H SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N660 CH.sub.3 H SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 N661 CH.sub.3 H SO.sub.2 N(CH.sub.3).sub.2 CH.sub. 3 CH.sub.3 N662 CH.sub.3 H SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3 CH663 CH.sub.3 H SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 CH664 CH.sub.3 H SO.sub.2 N(C.sub.2 H.sub.5).sub.2 OCH.sub.3 OCH.sub.3 CH665 CH.sub.3 H SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 N666 CH.sub.3 H SO.sub.2 N(C.sub.2 H.sub.5).sub.2 OCH.sub.3 OCH.sub.3 N667 CH.sub.3 H SO.sub.2 NHCH.sub.3 CH.sub.3 CH.sub.3 CH668 CH.sub.3 H SO.sub.2 NHCH.sub.3 CH.sub.3 OCH.sub.3 CH669 CH.sub.3 H SO.sub.2 NHCH.sub.3 CH.sub.3 OCH.sub.3 N670 CH.sub.3 H SO.sub.2 NHC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH671 CH.sub.3 H SO.sub.2 NHC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH672 CH.sub.3 H SO.sub.2 NHC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N673 H CH.sub.3 SCH.sub.3 CH.sub.3 CH.sub.3 CH674 H CH.sub.3 SCH.sub.3 CH.sub.3 OCH.sub.3 CH675 H CH.sub.3 SCH.sub. 3 CH.sub.3 OCH.sub.3 N676 H CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH677 H CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH678 H CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N679 H CH.sub.3 SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH680 H CH.sub.3 SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH681 H CH.sub.3 SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N682 H CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 CH683 H CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 CH684 H CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n OCH.sub.3 OCH.sub.3 CH685 H CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 N686 H CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n OCH.sub.3 OCH.sub.3 N687 H CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH688 H CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH689 H CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N690 H CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3 CH691 H CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 CH692 H CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 N693 H H SO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH694 H H SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH695 H H SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N696 H H SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 CH697 H H SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 CH698 H H SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 N699 H H SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH700 H H SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH701 H H SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N702 H H SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3 CH703 H H SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 CH704 H H SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 N705 ##STR199## CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH706 ##STR200## CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH707 ##STR201## CH.sub.3 SO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N708 ##STR202## CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 CH.sub.3 CH709 ##STR203## CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 CH710 ##STR204## CH.sub.3 SO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 N711 ##STR205## CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH712 ##STR206## CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub. 3 CH713 ##STR207## CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N714 ##STR208## CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3 CH715 ##STR209## CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 CH716 ##STR210## CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 N717 CH.sub.3 H H CH.sub.3 CH.sub.3 CH718 CH.sub.3 H H CH.sub.3 OCH.sub.3 CH719 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH720 CH.sub.3 H H CH.sub.3 OCH.sub.3 N721 CH.sub.3 H H OCH.sub.3 OCH.sub.3 N722 H H H CH.sub.3 CH.sub.3 CH723 H H H CH.sub.3 OCH.sub.3 CH724 H H H OCH.sub.3 OCH.sub.3 CH725 H H H CH.sub.3 OCH.sub.3 N726 H H H OCH.sub.3 OCH.sub.3 N727 CH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub. 3 OCH.sub.3 CH728 CH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 N729 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 ##STR211## CH.sub.3 CH.sub.3 CH730 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 ##STR212## CH.sub.3 OCH.sub.3 CH731 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 ##STR213## OCH.sub.3 OCH.sub.3 CH732 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 ##STR214## CH.sub.3 OCH.sub.3 N733 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.3 ##STR215## OCH.sub.3 OCH.sub.3 N734 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 CH.sub.3 CH735 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 OCH.sub.3 CH736 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -i OCH.sub.3 OCH.sub.3 CH737 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -i CH.sub.3 OCH.sub.3 N738 CH.sub.3 CH.sub.3 CO.sub. 2 C.sub.3 H.sub.7 -i OCH.sub.3 OCH.sub.3 N739 CH.sub.3 H H CH.sub.3 OCH.sub.2 CH.sub.2 C740 CH.sub.3 H H CH.sub.3 Cl C(CH.sub.2).sub.2 Cl741 CH.sub.3 H H CH.sub.3 CH.sub.3 N742 CH.sub.3 CH.sub.3 SC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH743 CH.sub.3 CH.sub.3 SC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH744 CH.sub.3 CH.sub.3 SC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH745 CH.sub.3 CH.sub.3 SC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N746 CH.sub.3 CH.sub.3 SC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 N747 CH.sub.3 CH.sub.3 ##STR216## CH.sub.3 CH.sub.3 CH748 CH.sub.3 CH.sub.3 ##STR217## CH.sub.3 OCH.sub.3 CH749 CH.sub.3 CH.sub.3 ##STR218## CH.sub.3 OCH.sub.3 N750 CH.sub.3 CH.sub.3 ##STR219## CH.sub.3 CH.sub.3 CH751 CH.sub.3 CH.sub.3 ##STR220## CH.sub.3 OCH.sub.3 CH752 CH.sub.3 CH.sub.3 ##STR221## OCH.sub.3 OCH.sub.3 CH753 CH.sub.3 CH.sub.3 ##STR222## CH.sub.3 OCH.sub.3 N754 CH.sub.3 CH.sub.3 ##STR223## OCH.sub.3 OCH.sub.3 N755 CH.sub.3 ##STR224## CH.sub.3 CH.sub.3 OCH.sub.3 CH756 CH.sub.3 ##STR225## CH.sub.3 CH.sub.3 OCH.sub.3 N757 CH.sub.3 ##STR226## CH.sub.3 CH.sub.3 OCH.sub.3 CH758 CH.sub.3 ##STR227## CH.sub.3 CH.sub.3 OCH.sub.3 N759 CH.sub.3 ##STR228## CH.sub.3 CH.sub.3 OCH.sub.3 CH760 CH.sub.3 ##STR229## CH.sub.3 CH.sub.3 OCH.sub.3 N761 CH.sub.3 ##STR230## CH.sub.3 CH.sub.3 OCH.sub.3 CH762 CH.sub.3 CH.sub.3 ##STR231## CH.sub.3 CH.sub.3 CH763 CH.sub.3 CH.sub.3 ##STR232## CH.sub.3 OCH.sub.3 CH764 CH.sub.3 CH.sub.3 ##STR233## OCH.sub.3 OCH.sub.3 CH765 CH.sub.3 CH.sub.3 ##STR234## CH.sub.3 OCH.sub.3 N766 CH.sub.3 CH.sub.3 ##STR235## OCH.sub.3 OCH.sub.3 N767 CH.sub.3 CH.sub.3 ##STR236## CH.sub.3 CH.sub.3 N768 CH.sub.3 CH.sub.3 ##STR237## Cl Cl N769 CH.sub.3 CH.sub.3 ##STR238## CH.sub.3 OCH.sub.3 CH770 CH.sub.3 CH.sub.3 ##STR239## CH.sub.3 OCH.sub.3 N771 CH.sub.3 CH.sub.3 ##STR240## CH.sub.3 OCH.sub.3 CH772 CH.sub.3 CH.sub.3 ##STR241## CH.sub.3 OCH.sub.3 N773 CH.sub.3 CH.sub.3 ##STR242## CH.sub.3 OCH.sub.3 CH774 CH.sub.3 CH.sub.3 ##STR243## CH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE 2__________________________________________________________________________ ##STR244##Comp. A B C X Y Z__________________________________________________________________________775 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 CH776 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 CH777 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH778 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 N779 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 N780 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH781 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH782 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N783 ##STR245## CH.sub.3 H CH.sub.3 OCH.sub.3 CH784 ##STR246## CH.sub.3 H CH.sub.3 OCH.sub.3 N785 ##STR247## H H CH.sub.3 OCH.sub.3 CH786 ##STR248## H H CH.sub.3 OCH.sub.3 N787 CH.sub.3 CH.sub.3 ##STR249## CH.sub.3 OCH.sub.3 CH788 CH.sub.3 CH.sub.3 ##STR250## CH.sub.3 OCH.sub.3 N789 CH.sub.3 CH.sub.3 Cl CH.sub.3 CH.sub.3 CH790 CH.sub.3 CH.sub.3 Cl CH.sub.3 OCH.sub.3791 CH.sub.3 CH.sub.3 Cl OCH.sub.3 OCH.sub.3 CH792 CH.sub.3 CH.sub.3 Cl CH.sub.3 OCH.sub.3 N793 CH.sub.3 CH.sub.3 Cl OCH.sub.3 OCH.sub.3 N794 CH.sub.3 H Cl CH.sub.3 CH.sub.3 CH795 CH.sub.3 H Cl CH.sub.3 OCH.sub.3 CH796 CH.sub.3 H Cl OCH.sub.3 OCH.sub.3 CH797 CH.sub.3 H Cl CH.sub.3 OCH.sub.3 N798 CH.sub.3 H Cl OCH.sub.3 OCH.sub.3 N799 CH.sub.3 CH.sub.3 NO.sub.2 CH.sub.3 CH.sub.3 CH800 CH.sub.3 CH.sub.3 NO.sub.2 CH.sub.3 OCH.sub.3 CH801 CH.sub.3 CH.sub.3 NO.sub.2 OCH.sub.3 OCH.sub.3 CH802 CH.sub.3 CH.sub.3 NO.sub.2 CH.sub.3 OCH.sub.3 N803 CH.sub.3 CH.sub.3 NO.sub.2 OCH.sub.3 OCH.sub.3 N804 CH.sub.3 H NO.sub.2 CH.sub.3 OCH.sub.3 CH805 CH.sub.3 H NO.sub.2 OCH.sub.3 OCH.sub.3 CH806 CH.sub.3 H NO.sub.2 CH.sub.3 OCH.sub.3 N807 CH.sub.3 CH.sub.3 Br CH.sub.3 OCH.sub.3 CH808 CH.sub.3 CH.sub.3 Br CH.sub.3 OCH.sub.3 N809 CH.sub.3 CH.sub.3 Br OCH.sub.3 OCH.sub.3 N810 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH811 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH812 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH813 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N814 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N815 CH.sub.3 H CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH816 CH.sub.3 H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH817 CH.sub.3 H CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH818 CH.sub.3 H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N819 CH.sub.3 H CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N820 CH.sub.3 H CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 N821 CH.sub.3 H CO.sub.2 CH.sub.3 CH.sub.3 Cl C(CH.sub.2).sub.2 Cl822 CH.sub.3 H CO.sub.2 CH.sub.3 CH.sub.3 Cl CH823 CH.sub.3 H CO.sub.2 CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 CH824 CH.sub.3 H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.2 CO.sub.2 CH.sub.3 CH825 CH.sub.3 H CO.sub.2 CH.sub.3 CH.sub.3 Cl N826 CH.sub.3 H CO.sub.2 CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 N827 CH.sub.3 H CO.sub.2 CH.sub.3 CH ##STR251## N828 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH829 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH830 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH831 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N832 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 N833 CH.sub.3 H CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH834 CH.sub.3 H CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH835 CH.sub.3 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH836 CH.sub.3 H CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N837 CH.sub.3 H CO.sub.2 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 N838 H CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH839 H CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH840 H CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N841 H H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH842 H H CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH843 H H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N844 H CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH845 H CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH846 H CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N847 H H CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH848 H H CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH849 H H CO.sub.2 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH850 H H CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N851 H H CO.sub.2 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 N852 ##STR252## H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH853 ##STR253## H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N854 CH.sub.2 H CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 CH855 CH.sub.3 H CO.sub.2 C.sub.3 H.sub.7 -n OCH.sub.3 OCH.sub.3 CH856 CH.sub.3 H CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 N857 CH.sub.3 H CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 CH858 CH.sub.3 H CO.sub.2 C.sub.3 H.sub.7 -n OCH.sub.3 OCH.sub.3 CH859 CH.sub.3 H CO.sub.2 C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 N860 CH.sub.3 H CO.sub.2 CH.sub.2 CHCH.sub.2 CH.sub.3 CH.sub.3 CH861 CH.sub.3 H CO.sub.2 CH.sub.2 CHCH.sub.2 CH.sub.3 OCH.sub.3 CH862 CH.sub.3 H CO.sub.2 CH.sub.2 CHCH.sub.2 CH.sub.3 OCH.sub.3 N863 CH.sub.3 H CO.sub.2 CH.sub.2 CCH.sub.2 CH.sub.3 CH.sub.3 CH864 CH.sub.3 H CO.sub.2 CH.sub.2 CCH.sub.2 CH.sub.3 OCH.sub.3 CH865 CH.sub.3 H CO.sub.2 C.sub.4 H.sub.9 -n CH.sub.3 OCH.sub.3 CH866 CH.sub.3 H CO.sub.2 C.sub.4 H.sub.9 -n CH.sub.3 OCH.sub.3 N867 C.sub.2 H.sub.5 H CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH868 C.sub.2 H.sub.5 H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH869 C.sub.2 H.sub.5 H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N870 CH.sub.3 H CO.sub.2 H CH.sub.3 CH.sub.3 CH871 CH.sub.3 H CO.sub.2 H CH.sub.3 OCH.sub.3 CH872 CH.sub.3 H CO.sub.2 H CH.sub.3 OCH.sub.3 N873 CH.sub.3 C.sub.2 H.sub.5 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH874 CH.sub.3 C.sub.2 H.sub.5 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N875 CH.sub.3 CH.sub.3 CON(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH876 CH.sub.3 CH.sub.3 CON(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH877 CH.sub.3 CH.sub.3 CON(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N878 CH.sub.3 CH.sub.3 CON(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 N879 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH880 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH881 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CH882 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub. 2 CH.sub.3 OCH.sub.3 N883 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 N884 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 N885 CH.sub.3 H SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH886 CH.sub.3 H SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH887 CH.sub.3 H SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N888 CH.sub.3 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 CH889 CH.sub.3 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 N890 CH.sub.3 CH.sub.3 ##STR254## CH.sub.3 OCH.sub.3 CH891 CH.sub.3 CH.sub.3 ##STR255## CH.sub.3 OCH.sub.3 N892 CH.sub.3 CH.sub.3 ##STR256## CH.sub.3 OCH.sub.3 CH893 CH.sub.3 CH.sub.3 ##STR257## CH.sub.3 OCH.sub.3 N894 CH.sub.3 CH.sub.3 ##STR258## CH.sub.3 OCH.sub.3 CH895 CH.sub.3 CH.sub.3 ##STR259## CH.sub.3 OCH.sub.3 CH896 H CH.sub.3 H CH.sub.3 CH.sub.3 CH897 H CH.sub.3 H CH.sub.3 OCH.sub.3 CH898 H CH.sub.3 H CH.sub.3 OCH.sub.3 N899 CH.sub.3 ##STR260## H CH.sub.3 OCH.sub.3 CH900 CH.sub.3 ##STR261## H OCH.sub.3 OCH.sub.3 CH901 CH.sub.3 ##STR262## H CH.sub.3 OCH.sub.3 N902 CH.sub.3 H ##STR263## CH.sub.3 OCH.sub.3 CH903 CH.sub.3 H ##STR264## OCH.sub.3 OCH.sub.3 CH904 CH.sub.3 H ##STR265## CH.sub.3 OCH.sub.3 N905 ##STR266## H Cl CH.sub.3 OCH.sub.3 CH906 ##STR267## H Cl OCH.sub.3 OCH.sub.3 CH907 ##STR268## H Cl CH.sub.3 OCH.sub.3 N908 ##STR269## H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH909 ##STR270## H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N910 ##STR271## H CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH911 ##STR272## H CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N912 ##STR273## CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH913 ##STR274## CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH914 ##STR275## CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N915 ##STR276## H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH916 ##STR277## H CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N917 ##STR278## CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH918 ##STR279## CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N919 ##STR280## H NO.sub.2 CH.sub.3 OCH.sub.3 CH920 ##STR281## H NO.sub.2 CH.sub.3 OCH.sub.3 N921 ##STR282## H CO.sub.2 H CH.sub.3 OCH.sub.3 CH922 ##STR283## H CO.sub.2 H CH.sub.3 OCH.sub.3 N923 ##STR284## H NO.sub.2 CH.sub.3 OCH.sub. 3 CH924 ##STR285## H NO.sub.2 CH.sub.3 OCH.sub.3 N925 CH.sub.3 CH.sub.3 Cl CH.sub.3 H CH926 CH.sub.3 CH.sub.3 Cl CH.sub.3 Cl CH927 CH.sub.3 CH.sub.3 Cl CH.sub.3 OCH.sub.2 CH.sub.2 C928 CH.sub.3 CH.sub.3 Cl CH.sub.3 CH.sub.3 N929 CH.sub.3 CH.sub.3 NO.sub.2 CH.sub.3 Cl CH930 CH.sub.3 CH.sub.3 NO.sub.2 CH.sub.3 OCH.sub.2 CH.sub.2 C931 CH.sub.3 CH.sub.3 NO.sub.2 CH.sub.3 CH.sub.3 N932 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 Cl CH933 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.2 CH.sub.2 C934 CH.sub.3 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 Cl N(CH.sub.3).sub.2 N__________________________________________________________________________
TABLE 3__________________________________________________________________________ ##STR286##Comp. No. A B C X Y Z__________________________________________________________________________935 CH.sub.3 H H CH.sub.3 CH.sub.3 CH936 CH.sub.3 H H CH.sub.3 OCH.sub.3 CH937 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH938 CH.sub.3 H H CH.sub.3 OCH.sub.3 N939 CH.sub.3 H H OCH.sub.3 OCH.sub.3 N940 CH.sub.3 H H CH.sub.3 CH.sub.3 N941 CH.sub.3 H H CH.sub.3 Cl CH942 CH.sub.3 H H CH.sub.3 OCH.sub.2 CH.sub.2 C943 CH.sub.3 H H N(CH.sub.3).sub.2 Cl N944 CH.sub.3 H H CH.sub.3 ##STR287## N945 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 CH946 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH947 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH948 CH.sub.3 CH.sub.3 H CH.sub.3 OCH.sub.3 N949 CH.sub.3 CH.sub.3 H OCH.sub.3 OCH.sub.3 N950 CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 CH951 CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CH952 CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 N953 ##STR288## H H CH.sub.3 OCH.sub.3 CH954 ##STR289## H H OCH.sub.3 OCH.sub.3 CH955 ##STR290## H H CH.sub.3 OCH.sub.3 N956 CH.sub.3 Cl H CH CH.sub.3 CH957 CH.sub.3 Cl H CH.sub.3 OCH.sub.3 CH958 CH.sub.3 Cl H OCH.sub.3 OCH.sub.3 CH959 CH.sub.3 Cl H CH.sub.3 OCH.sub.3 N960 CH.sub.3 Cl H OCH.sub.3 OCH.sub.3 N961 CH.sub.3 Br H CH.sub.3 OCH.sub.3 CH962 CH.sub.3 Br H OCH.sub.3 OCH.sub.3 CH963 CH.sub.3 Br H CH.sub.3 OCH.sub.3 N964 CH.sub.3 NO.sub.2 H CH.sub.3 CH.sub.3 CH965 CH.sub.3 NO.sub.2 H CH.sub.3 OCH.sub.3 CH966 CH.sub.3 NO.sub.2 H OCH.sub.3 OCH.sub.3 CH967 CH.sub.3 NO.sub.2 H CH.sub.3 OCH.sub.3 N968 CH.sub.3 NO.sub.2 H OCH.sub.3 OCH.sub.3 N969 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH970 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH971 CH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH972 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N973 CH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N974 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 CH975 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 H CH.sub.3 OCH.sub.3 CH976 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH977 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 H CH.sub.3 OCH.sub.3 N978 CH.sub.3 CO.sub.2 C.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 N979 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -n H CH.sub.3 OCH.sub.3 CH980 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -n H OCH.sub.3 OCH.sub.3 CH981 CH.sub.3 CO.sub.2 C.sub.3 H.sub.7 -n H CH.sub.3 OCH.sub.3 N982 CH.sub.3 CO.sub.2 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 CH983 CH.sub.3 CO.sub.2 CH.sub.2 CHCH.sub.2 H OCH.sub.3 OCH.sub.3 CH984 CH.sub.3 CO.sub.2 CH.sub.2 CHCH.sub.2 H CH.sub.3 OCH.sub.3 N985 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 CH986 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH987 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 N989 CH.sub.3 CON(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH990 CH.sub.3 CON(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH991 CH.sub.3 CON(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N992 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH993 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH994 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N995 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H CH.sub.3 OCH.sub.3 CH996 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H OCH.sub.3 OCH.sub.3 CH997 CH.sub.3 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H CH.sub.3 OCH.sub.3 N998 CH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH999 CH.sub.3 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH1000 CH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N1001 H H H CH.sub.3 OCH.sub.3 CH1002 H H H OCH.sub.3 OCH.sub.3 CH1003 H H H CH.sub.3 OCH.sub.3 N1004 C.sub.2 H.sub.5 H H CH.sub.3 CH.sub.3 CH1005 C.sub.2 H.sub.5 H H CH.sub.3 OCH.sub.3 CH1006 C.sub.2 H.sub.5 H H OCH.sub.3 OCH.sub.3 CH1007 C.sub.2 H.sub.5 H H CH.sub.3 OCH.sub.3 N__________________________________________________________________________
The compounds of this invention represented by the above formula (I) can readily be produced by selecting suitably the following reaction scheme 1, 2 or 3. ##STR291## wherein A, B, C, D, X, Y and Z have the same meanings as defined above.
That is, a pyrazolesulfonylisocyanate derivative (IV) is dissolved in an inert solvent such as sufficiently dried dioxane, acetonitrile, etc., and to the resultant solution is added pyrimidine or a triazine derivative (V). By stirring the mixture, the reaction proceeds generally rapidly to give the compound (I) of this invention. In case when the reaction proceeds difficulty, a minute amount of a suitable base such as triethylamine, triethylenediamine, pyridine, sodium ethoxide, sodium hydride, etc. may be added to the reaction mixture, whereby the reaction can proceed easily. ##STR292## wherein A, B, C, D, X, Y and Z have the same meanings as defined above, and R.sub.9 represents an alkyl group or a phenyl group.
That is, a pyrazolesulfonamide (VI) is allowed to react with a chlorocarbonate in a solvent such as acetone or methyl ethyl ketone in the presence of a base such as potassium carbonate, followed by acid precipitation with hydrochloric acid, etc., to give a compound (VII). This compound is then heated in a solvent such as toluene with a compound (V) to give the compound (I) of this inventions. ##STR293## wherein A, B, C and Z have the same meanings as defined above, E represents a halogen atom, G represents H, Cl, Br, C.sub.1 -C.sub.4 alkyl, CF.sub.3, methoxymethyl or methoxy ethyl, and R.sub.10 represents a lower alkyl group.
By referring to Japanese Unexamined Patent Publication No. 154471/1981, a pyrazolesulfonamide derivative (VI) can be allowed to react with a pyrimidine or a triazine isocyanate (X) to synthesize a compound (VIII), which is a part of the compound of this invention, followed by reaction with a sodium alcoholate, to further synthesize a compound (IX), which is also a part of the compounds of this invention.
The other reactant aminopyrimidine can be synthesized by referring to "The Chemicsty of Heterocyclic Compounds (Interscience Publishers Inc., New York) Vol. 16, The pyrimidines".
Aminotriazine can be synthesized according to the method disclosed in "Journal of Organic Chemistry, Vol. 28, pp. 1812-1821 (1963)".
2-Amino-4-methyl-5,6-dihydrofura[2,3-d]pyrimidine and 2-amino-4-chloro-5-chloroethyl-6-methylpyrimidine can be synthesized accordng to the method disclosed in Journal of Organic Chemistry, Vol. 16, pp. 1153 (1951).
Most of the pyrazolesulfonamide (VI) or the pyrazolesulfonyl isocyanate derivative (IV) used as the starting material in the reaction scheme 1, 2 or 3 are novel compounds, and they can be synthesized by selecting suitably the following reaction scheme 4, 5 or 6. ##STR294##
Most of the pyrazolesulfonyl isocyanate derivatives obtained hereinabove are unstable in the air, and should preferably be stored in a cold and dark place under a nitrogen atmosphere when they are to be stored, but alternatively they can be used as such without purification in many cases in the subsequent reaction step.
Most of the intermediates pyrazolesulfonamides (VI) to be used in this invention are novel compounds, and synthetic examples thereof are shown below as Reference examples.
REFERENCE EXAMPLE 1
Synthesis of 1,3-dimethyl-5-methoxypyrazole-4-sulfonamide:
Into 70 ml of chlorosulfonic acid was added dropwise under cooling at 5.degree. C. or lower 12.6 g (0.1 mol) of 1,3-dimethyl-5-methoxypyrazole. After the addition, the mixture was stirred at 100.degree. C. for 8 hours. Then, the reaction mixture was cooled to 80.degree. C., followed by dropwise addition of 11.9 g (0.1 mol) of thionyl chloride over 30 minutes. After the dropwise addition, the mixture was stirred at 100.degree. C. for 2 hours. The reaction mixture was cooled and poured carefully into ice-water, whereby crude 1,3-dimethyl-5-methoxy-pyrazole-4-sulfonylchloride was formed as crystals The crystals were separated by filtration, dissolved in 20 ml of tetrahydrofuran and the resultant solution was added dropwise into 100 ml of aqueous ammonia (28%) at 10.degree. C. or lower. After the addition, the mixture was stirred at room temperature for 30 minutes. The reaction mixture was evaporated under reduced pressure to remove low boiling components, whereby crystals were precipitated. The crystals were filtered, washed with water and dried to give 11.5 g of 1,3-dimethyl-5-methoxypyrazole-4-sulfonamide melting at 144.degree.-146.degree. C.
REFERENCE EXAMPLE 2
Synthesis of 1,5-dimethyl-3-trifluoromethylpyrazole-4-sulfonamide:
Into 100 ml of an ethanolic solution of 25 g (0.16 mol) of trifluoroacetylacetone, there was added dropwise 7.4 g (0.16 mol) of methylhydrazine. After stirring at room temperature for 3 hours, the mixture was left to stand overnight and the solvent was evaporated to give 19.2 g of 1,5-dimethyl-3-trifluoromethylpyrazole as an oil. Following then the procedures as Reference example 1, this product was allowed to react with chlorosulfonic acid and then with thionyl chloride to obtain 29 g of 1,5-dimethyl-3-trifluoromethylpyrazole-4-sulfonyl-chloride, which was in turn reacted with aqueous ammonia (28%) in tetrahydrofuran to give 21.5 g of 1,5-dimethyl-3-trifluoromethylpyrazole-4-sulfonamide melting at 204.degree.-206.degree. C.
REFERENCE EXAMPLE 3
Synthesis of 1,3-dimehyl-5-methoxycarbonylpyrazole-4-sulfonamide:
Into 200 ml of chlorosulfonic acid, there was added dropwise 50.4 g (0.3 mol) of Ethyl 1,3-dimethyl-5-pyrazole carboxylate under cooling at 5.degree. C. or lower. After heating at 120.degree. C. under stirring for 10 hours, the reaction mixture was poured into ice-water and extracted with ether. After washing with water and drying, evaporation of the solvent gave 49 g of crude 1,3-dimethyl-4-chlorosulfonyl-5-pyrazole carboxylic acid as a solid.
23.9 g (0.1 mol) of this product was dissolved in 60 ml of tetrahydrofuran and the resultant solution was added dropwise into 150 ml of aqueous ammonia (28%) at 10.degree. C. or lower. The mixture was stirred at room temperature for 4 hours and concentrated to dryness under reduced pressure. Then, 300 ml of dry methanol was added to the mixture, and the mixture was refluxed for 3 hours while passing gaseous hydrogen chloride thereinto. After the reaction, methanol was evaporated and ice-water was added to the residue, followed by extraction with ethyl acetate. After washing with water and drying, the solvent was evaporated and the crude crystals obtained were recrystallized from methanol to give 9.0 g of 1,3-dimethyl-5-methoxycarbonylpyrazole-4-sulfonamide melting at 174.degree.-176.degree. C.
REFERENCE EXAMPLE 4
Synthesis of 1,3-dimethyl-5-n-propylsulfonylpyrazole-4-sulfonamide:
With the use of 1,3-dimethyl-5-chloropyrazole as the starting material, following the procedure in the above Reference examples, there was obtained 5-chloro-1,3-dimethylpyrazole-4-sulfonamide melting at 173.degree. C. Into a mixture of 14.1 g (0.067 mol) of the above sulfonamide, 10.7 g (0.268 mol) of sodium hydroxide and 120 ml of DMF, 6.6 g (0.087 mol) of n-propylmercaptan was added dropwise at room temperature. After the addition, the mixture was heated at 80.degree.to 90.degree. C. for 3 hours. After completion of the reaction, DMF was evaporated under reduced pressure, and the residue was diluted with water, adjusted to pH 4 with conc. hydrochloric acid and the precipitated crystals were collected by filtration. After drying, there was obtained 14.3 g of 1,3-dimethyl-5-n-propylthio-pyrazole-4-sulfonamide melting at 105.degree.-106.degree. C.
As the next step, this intermediate was dissolved in 80 ml of acetic acid and 23 g of 30% aqueous hydrogen peroxide was added dropwise into the resultant solution under ice-cooling. After stirring at room temperature for 4 hours, the reaction mixture was poured into water The precipitated crystals were collected by filtration to obtain 14 g of 1,3-dimethyl-5-n-propylsulfonylpyrazole-4-sulfonamide melting at 127.degree.-129.degree. C.
Following the procedures as described in Reference examples 1 to 4, there were synthesized the substituted pyrazolesulfoamides (IV) shown below
REFERENCE EXAMPLE 5
Synthesis of 1,5-dimethyl-3-phenylpyrazole-4-sulfonamide:
Obtained, following the above Reference examples, from 1,5-dimethyl-3-phenylpyrazole. m.p. 144.degree.-148.degree. C.
REFERENCE EXAMPLE 6
Synthesis of 5-chloro-1-methylpyrazole-4-sulfonamide:
Obtained from 5-chloro-1-methylpyrazole. m.p. 159.degree.-152.degree. C.
REFERENCE EXAMPLE 7
Synthesis of 1,5-dimethyl-3-methoxycarbonylpyrazole-4-sulfonamide:
Obtained from 1,5-dimethyl-3-methoxycarbonylpyrazole. m.p. 183.degree.-185.degree. C.
REFERENCE EXAMPLE 8
Synthesis of 1,5-dimethyl-3-ethoxycarbonylpyrazole-4-sulfonamide:
Obtained from 1,5-dimethyl-3-ethoxycarbonylpyrazole. m.p. 159.degree.-161.degree. C.
REFERENCE EXAMPLE 9
Synthesis of 1,3-di-methylpyrazole-4-sulfonamide:
Obtained from 1,3-dimethylpyrazole. m.p. 114.degree.-115.degree. C.
Reference example 10:
Synthesis of 3,5-dimethylpyrazole-4-sulfonamide:
Obtained from 3,5-dimethylpyrazole. m.p.215.degree.-223.degree. C.
Reference example 11:
Synthesis of 1,5-dimethylpyrazole-4-sulfonamide:
Obtained from 1,5-dimethylpyrazole. m.p.165.degree.-166.degree. C.
Reference example 12:
Synthesis of 5-methoxy-1-methyl-3-i-propylpyrazole-4-sulfonamide:
Obtained from 5-methoxy-1-methyl-3-i-propylpyrazole. m.p.114.degree.-115.degree. C.
Reference example 13:
Synthesis of 1,3-dimethyl-5-ethoxycarbonylpyrazole-4-sulfonamide:
Obtained from 1,3-dimethyl-5-ethoxycarbonylpyrazole. m.p.150.degree.-154.degree. C.
Reference example 14:
Synthesis of 3,5-dimethyl-1-phenylpyrazole-4-sulfonamide:
Obtained from 3,5-dimethyl-1-phenylpyrazole. m.p.178.degree.-180.degree. C.
Reference example 15:
Synthesis of 3-ethoxycarbonyl-1-methyl-5-phenylpyrazole-4-sulfonamide:
A solution of 7.5 ml of chlorosulfonic acid and 15 xl of dry chloroform was cooled to 0.degree. C., and a solution of 11.5 g (0.05 mol) of 3-ethoxycarbonyl-1-methyl5-phenylpyrazole in 25 ml of dry chloroform was added dropwise thereinto. Then, the mixture was stirred at room temperature for one hour and under reflux for 3 hours. After the reaction, by evaporation of chloroform, there was obtained oily 3-ethoxycarbonyl-1-methyl-5-phenylpyrazole-4-sulfonic acid. As the next step, at room temperature 20.9 g of phosphorus pentachloride was added portionwise, followed by stirring at 90.degree. to 100.degree. C. for one hour. The reaction mixture was added into ice-water and extracted with ether to obtain 14.7 g of 3-ethoxycarbonyl-1-methyl-5-phenylpyrazole-4-sulfonylchloride. Then, the resultant sulfonylchloride was dissolved in 20 ml of acetone and 4.48 g of KHCO was added to the solution. After a solution of 2.7 g of aqueous ammonia (28 %) and 6.5 ml of acetone was added dropwise thereinto at room temperature, the mixture was heated at 50 to 60 .degree. C. for 30 minutes. After evaporation of acetone, water was added to the residue, whereby 12.9 g of the title compound was precipitated as a solid. Recrystallization from benzene gave 8.4 g of the product. m.p. 141.degree.-144.degree. C.
Following the procedures as described above, there were synthesized the substituted pyrazolesulfonamides shown below.
Reference example 16:
Synthesis of 5-chloro-1,3-dimethylpyrazole-4-sulfonamide:
Obtained from 5-chloro-1-3-dimethylpyrazole. m.p. 173.degree. C.,
Reference example 17:
Synthesis of 1-ethyl-5-methyl-3-methoxycarbonyl-pyrazole-4-sulfonamide:
Obtained from 1-ethyl-5-methyl-3-methoxycarbonylpyrazole. m.p. 165.degree.-168.degree. C.,
Reference example 18:
Synthesis of 5-ethyl-1-methyl-3-methoxycarbonylpyraxole-4-sulfonamide:
Obtained from 5-ethyl-1-methyl-3-methoxycarbonylpyrazole. m.p. 188.degree.-191.degree. C.
Reference example 19:
Synthesis of 1-ethyl-3-methyl-5-methoxycarbonyl-pyrazole-4-sulfonamide:
Obtained from 1-ethyl-3-methyl-5-methoxycarbonylpyrazole. m.p. 130.degree.-133.degree. C.,
Reference example 20
Synthesis of 3-ethyl-1-methyl-5-methoxycarbonyl-pyrazole-4-sulfonamide:
Obtained from 3-ethyl-1-methyl-5-methoxycarbonylpyrazole. m.p. 162.degree.-165.degree. C.,
Reference example 21:
Synthesis of 1,3-dimethyl-5-dimethylcarbamoylpyrazole-4-sulfonamide:
Obtained from 1,3-dimethyl-5-dimethylcarbamoylpyrazole. m.p. 150.degree.-152.degree. C.
Reference example 22:
Synthesis of 1-methylpyrazole-4-sulfonamide:
Obtained from 1-methylpyrazole. m.p. 122.degree.-123.degree. C.
Reference example 23:
Synthesis of 1,3-dimethyl-5-i-propoxycarbonylpyrazole-4-sulfonamide:
Obtained by heating 1,3-dimethyl-5-carboxylpyrazole-4-sulfonamide obtained in Reference example 3 in i-propyl alcohol in the co-presence of hydrogen chloride m.p. 105.degree.-108.degree. C.,
Reference example 24:
Synthesis of 1,3-dimethyl-5-(N,N-tetramethylene-carbamoyl)-4-sulfonamide:
Obtained from 1,3-dimethyl-5-(N,N-tetramethylenecarbamoyl)pyrazole. m.p. 92.degree.-95.degree. C.
Reference example 25: Synthesis of 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide:
(1) Synthesis of ethyl-5-hydroxy-1-methyl-4-pyrazolecarboxylate
To a solution of 216 g (1 mol) of diethylethoxymethylenemalonate in 216 g of ethanol, there was added 46 g (1 mol) of methylhydrazine at 10.degree. C. Then, at room temperature, the mixture was stirred and further refluxed for one hour, and thereafter the reaction mixture was left to stand. The precipitated crystals were filtered and dried to obtain 148 g of the title compound melting at 134.degree.-135.degree. C.
(2) Synthesis of ethyl 5-chloro-1-methyl-4-pyrazole carboxylate:
A mixture of 10 g of ethyl 5-hydroxy-1-methyl-4-pyrazole carboxylate and 50 ml of phosphorus oxychloride was stirred at 90.degree. to 100.degree. C. for 65 hours. Excessive phosphorus oxychloride was evaporated under reduced pressure, and the residue was poured into ice-water. The precipitated crystals were filtered and dried to obtain 4.5 g of 5-chloro-1-methyl-4-pyrazole carboxylic acid. The filtrate was neutralized with aqueous ammonia (28%) and extracted with ether. After drying of the extract, evaporation of the solvent gave 4.0 g of ethyl 5-chloro-1-methyl-4-pyrazole carboxylate. To 5-chloro-1-methyl-4-pyrazole carboxylic acid were added 30 ml of thionyl chloride and 0.2 ml of dimethylformamide, and the mixture was refluxed for 5 hours. Then, excessive thionyl chloride was evaporated and the residue was added to dry ethanol. After stirring at room temperature for 3 hours, the solvent was evaporated and ether was added to the residue. After washing with water, drying and evaporation of the solvent, there was obtained 4.5 g of ethyl 5-chloro-1-methyl-4-pyrazole carboxylate as an oil. Total of the title compound: 8.5 g.
(3) Synthesis of ethyl 5-mercapto-1-methyl-4-pyrazole carboxylate:
After 2.2 g (0.094 mol) of sodium was dissolved in 35 ml of ethanol, 50 ml of dimethylformamide was added to the resultant solution, and most of ethanol was removed. Then, under cooling, hydrogen sulfide was passed into the mixture to saturation, followed by addition of 7.4 g (0.039 ml) of ethyl 5-chloro-1-methyl-4-pyrazole carboxylate. After stirring at 70 to 80 .degree. C. for 3.5 hours, the reaction mixture was concentrated under reduced pressure Ice-water was added to the reside, and insolubles were filtered off. The filtrate was made acidic, extracted with chloroform and dried, followed by evaporation of the solvent, to give 6.8 g of the title compound as an oil.
(4) Synthesis of 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide:
To 100 ml of a 28 % aqueous ammonia, there was added 20 ml of aqueous solution containing 7.1 g of ethyl-5-mercapto-1-ethyl-4-pyrazole carboxylate and 1.6 g of sodium hydroxide. To this reaction mixture was added 61 g of 6 % aqueous NaOCl solution at 5.degree.-10.degree. C. The precipitated crystals were filtered and washed with water. The resultant moist sulfenamide (5.6g) was suspended in water and an aqueous saturated solution of 5.5 g of potassium permanganate was added to the suspension at room temperature. After stirring vigorously at room temperature, the mixture was filtered. The filtrate was made acidic and extracted with ethyl acetate. After drying, the solvent was evaporated to obtain 1.8 g of the title compound. m.p. 102.degree.-104.degree. C.
(5) Synthesis of 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide (alternative method):
A solution of 3.0 g of ethyl 5-mercapto-1-methyl-4-pyrazole carboxylate in 50 ml acetic acid was stirred while passing chlorine at 15 to 20 .degree. C. Then, after nitrogen was passed into the mixture, the reaction mixture was poured into ice-water and the crystals precipitated were separated by filtration.
The sulfonyl chloride as prepared above was dissolved in 20 ml of tetrahydrofuran, and added under ice-cooling to 50 ml of 28 % aqueous ammonia. After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The precipitated crystals were filtered, washed with water and further washed with n-hexane. After drying, 1.3 g of the title compound was obtained. m.p. 102.degree.-104.degree. C.
Reference example 26
Synthesis of 4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide:
Synthesized similarly as in Reference example 25. m.p. 127.degree.-128.degree. C.,
The respective intermediates have the following physical properties.
Methyl 5-hydroxy-1-methyl-4-pyrazole carboxylate: m.p. 111.degree.-113.degree. C.,
Methyl 5-chloro-1-methyl-4-pyrazole carboxylate: m.p. 70.degree.-71.degree. C.,
Methyl 5-mercapto-1-methyl-4-pyrazole carboxylate: m.p. 64.degree.-66.degree. C.,
Reference example 27:
Synthesis of 1,3-dimethylpyrazole-5-sulfonamide and 4-chloro-1,3-dimethyllpyrazole-5-sulfonamide
(1) Synthesis of 1,3-dimethyl-5-mercaptopyrazole
To a solution of 84 g (0.75 mol) of 1,3-dimethyl-5-hydroxypyrazole in 630 ml of xylene was added portionwise 65.3 g (0.294 mol) of phosphorus penlasulfide at 110.degree. to 120.degree. C. After heating under reflux for 1.5 hours, the hot reaction mixture was filtered. The filtrate was concentrated to give 21.4 g of the title compound m.p. 130 -132.degree. C.
(2) Synthesis of 4-chloro-1.3-dimethylpyrazole-5-sulfonamide
Into a solution of 12 g (0.094 ml) of the mercaptopyrazole obtained above in a mixture of acetic acid (100 ml) and water (15 ml), chlorine was passed at 10.degree. C. for 2 hours. After completion of the reaction, the mixture was poured into ice-water and extracted with ether. The organic extracts were washed with water, dried and evaporated to give 19.5 g of crude 4-chloro-1,3-dimethylpyrazole-5-sulfonyl chloride as an oil.
Then, into 130 ml of aqueous ammonia (28 %) was added dropwise the sulfonyl chloride obtained above in 50 ml of THF at 10.degree. C. or lower. After the addition, the reaction mixture was stirred at room temperature for 3 hours and then concentrated under reduced pressure to form precipitates.
The precipitated solids were filtered, washed with water and dried to give 10.8 g of the title compound. m.p. 135.degree.-138.degree. C.
Further, the filtrate obtained above was extracted with benzene several times and the aqueous layer was concentrated under reduced pressure to dryness. The residual product was extracted with 100 ml of ethyl acetate. After evaporation of the solvent there was also obtained 4.0 g of 1,3-dimethylpyrazole-5-sulfonamide. m.p. 63 -66.degree. C.
Reference example 28:
Synthesis of 1,3-dimethyl-4-nitropyrazole-5-sulfonamide
(1) Synthesis of 5-chloro-1,3-dimethyl-4-nitropyrazole
Concentrated H.sub.2 SO.sub.4 (35 g) was added to 10 ml of 90% HNO.sub.3 and at 75.degree.-85.degree. C., 13 g (0.1 mol) of 5-chloro-1,3-dimethylpyrazole was added dropwise with stirring to maintain the temperature at 85.degree. C. After completion of the addition, the mixture was heated at 75 -85.degree. C. for 1.5 hr. The nitration mixture was cooled and poured into ice. The suspension was filtered and the solid was washed with water and dried to give 14.5 g of the title compound. m.p. 70.degree. C.
(2) Synthesis of 5-benzylthio-1,3-dimethyl-4-nitropyrazole
Benzylmercaptan (50.8 g) (0.41 mol) was added to 21 g of sodium methoxide in 480 ml of DMF under ice-cooling and then 65.2 g (0.37 ml) of 5-chloro-2,3-dimethyl-4-nitropyrazole was added. After stirring at room temperature for 3 hr., DMF was evaporated under reduced pressure, and the residue was diluted with ice-water. The precipitated solids were filtered, washed with water and further with n-hexane and dried to give 82.4 g of the title compound. m.p. 82 -83.degree. C.
(3) Synthesis of 1,3-dimethyl-4-nitropyrazole-5-sulfonamide
Into a solution of 40 g (0.152 mol) of 5-benzylthio-1,3-dimethyl-4-nitropyrazole in 300 ml of acetic aid and 30 ml of water chlorine was passed at 3 to 8.degree. C. for 1.5 hr. After completion of the reaction, the mixture was poured into ice-water and extracted with ether to give crude 1,3-dimethyl-4-nitropyrazole-5-sulfonylchloride as an oil.
The sulfonylchloride obtained above in 50 ml of THF was added into 150 ml of aqueous ammonia (28%) under ice-cooling. After stirring at room temperature for 5 hrs, the reaction mixture was evaporated under reduced pressure. The precipitated solids were filtered, washed with water and further with n-hexane and dried to give 19.6 g of the title compound. m.p. 138.degree.-140.degree. C.
Reference example 29:
Synthesis of 1,3-dimethyl-4-dimethylsulfamoylpyrazole-5-sulfonamide:
(1) Syntheisis of N,N-dimethyl-(5-chloro-1,3-dimethylpyrazole)-4-sulfonamide
Into 150 xl of chlorosulfonic acid was added dropwise under cooling at 5.degree. C. or lower, 30 g (0.23 ml) of 5-chloro-1,3-dimethylpyrazole. After the addition, the mixture was stirred at 100.degree. C. for 8 hours. Then, the reaction mixture was cooled to 80.degree. C., followed by dropwise addition of 36 g of thionyl chloride over 30 minutes After the addition, the mixture was stirred at 100.degree. C. for an additional 2 hours. The reaction mixture was cooled on ice and poured carefully into ice-water, whereby crude 5-chloro-1,3-dimethylpyrazole-4-sulfonylchloride (50 g) was formed as crystals. Subsequently, into a solution of 40 g of dimethylamine in 250 ml of THF, the above compound was added under cooling and the reaction mixture was stirred at room temperature for 3 hours. After the reaction, THF was evaporated under reduced pressure and into the residue was added ether and washed with water. After drying and evaporating the etherial solution, there was obtained 47 g of the title compound m.p. 53 -55.degree. C.
(2) Synthesis of N,N-dimethyl-(5-benzylthio-1,3-dimethylpyrazole)-4-sulfonamid
Obtained, following the above Reference example 28-(2), from N,N-dimethyl-(5-chloro-1,3-dimethylpyrazole)-4-sulfonamide. m.p. 108 -109.degree. C.
(3) Synthesis of 1,3-dimethyl14-dimethylsulfamoyl-pyrazole-5-sulfonamide
Obtained, following the above Reference example 28-(3), from N,N-dimethyl-(5-benzylthio-1,3-dimethylpyrazole)-4-sulfoamide. m.p. 209.degree.-210.degree. C.
Reference example 30:
Synthesis of 1-methylpyrazole-3-sulfonamide:
To a solution of 32 g (0.33 mol) of 1-methyl-3-aminopyrazole in a mixture of conc. hydrochloric acid (120 ml) and acetic acid (40 ml) was added a solution of 34.1 g (0.494 mol) of sodium nitrite in water (80 ml at -10.degree. to 0.degree. C. The solution was stirred at -5.degree. C. for 30 minutes and then added, in several portions, into a sulfur dioxide saturated solution of acetic aid (440 ml) containing 6.7 g of cuprous chloride at -10.degree. to -5.degree. C. The resulting solution was stirred at 0.degree. to 5.degree. C. for 4 hours and then poured into ice-water and extracted with ether. The extracts were washed with water and saturated aqueous sodium bicarbonate, dried and evaporated to give 20.8 g of crude sulfonylchloride as an oil. The sulfonylchloride obtained above was dissolved in 50 ml of THF and added to 150 ml of aqueous ammonia (28%) at 10.degree. C. or lower. After stirring at room temperature for 3 hours, the reaction mixture was concentrated under reduced pressure to form precipitates. The precipitated solids were filtered, washed with water and further with n-hexane and dried to give 24. g of the title compound. m.p. 156 -158.degree. C.
Specific synthetic examples of the compounds according to this invention are illustrated below by using the substituted pyrazolesulfonamides (VI) obtained in Reference examples, but this invention is not limited thereto.

EXAMPLE 1
Synthesis of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-dimethyl-5-methoxypyrazole-4-sulfonamide (Compound No. 292):
To a mixture of 10.25 g (0.05 mol) of the sulfonamide obtained in Reference example 1, 8.29 g (0.06 mol) of dry potassium carbonate and 50 ml of dry acetone was added 4.95 g (0.05 mol) of n-butyl isocyanate at room temperature, and the mixture was stirred for 4 hours. Then, the reaction mixture was refluxed for one hour. After the reaction, acetone was evaporated under reduced pressure and the residue was dissolved in 200 ml of water. After separation of a trace of water insolubles, the filtrate was made acidic with hydrochloric acid and the crystals formed were filtered, washed with water and dried to give 9.2 g of N-(butylcarbamoyl)-1,3-dimethyl-5-methoxypyrazole-4-sulfonamide melting at 135 -142 .degree. C.
Into a mixture of 100 ml of dry benzene and 9.12 g (0.03 mol) of N-(n-butylcarbamoyl)-1,3-dimethyl-5-methoxypyrazole-4-sulfonamide, under reflux, 8.9 g (0.09 mol) of phosgene was passed over 1.5 hours. Then, the reaction mixture was further refluxed for 30 minutes. After completion of the reaction, evaporation of benzene under reduced pressure gave crude 1,3-dimethyl-5-methoxypyrazole-4-sulfonyl isocyanate as an oil.
The crude isocyanate was taken out in an amount of 1.39 g (0.006 mol), dissolved in 20 ml of dry acetonitrile and 0.695 g (0.005 mol) of 4-methoxy-6-methyl-2-aminopyrimidine was added to the resultant solution. The mixture was stirred at room temperature for one hour, then refluxed for 30 minutes, followed by cooling.
The crystals formed were filtered, washed and dried to obtain 1.09 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-dimethyl-5-methoxypyrazole-4-sulfonamide melting at 183.degree.-184.degree. C.
EXAMPLE 2
Synthesis of N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-carbonyl]-1,3-dimethyl-5-methoxycarbonylpyrazole-4-sulfonamide (Compound No. 387):
With the use of 6.8 g of the sulfonamide obtained in Reference example 3, following the procedure as in Example 1, there was obtained 8.6 g (0.026 mol) of N-(n-butylcarbamoyl)-1,3-dimethyl-5-methoxycarbonylpyrazole-4-sulfonamide. The compound obtained was mixed into 200 ml of xylene and under reflux 7.7 g (0.078 mol) of phosgene was passed into the mixture over 1.5 hours. The reaction mixture was refluxed for 30 minutes, followed by evaporation of xylene, to obtain crude 1,3-dimethyl-5-methoxycarbonylpyrazole-4-sulfonyl isocyanate as an oil.
The crude isocyanate was taken out in an amount of 0.90 g (0.0035 mol) and dissolved in 20 ml of dry acetonitrile and 0.35 g of (0.0025 mol) of 2-amino-4-methoxy-6-methyl-5-triazine was added to the solution. After the mixture was stirred at room temperature for 2 hours, the reaction mixture was refluxed for 30 minutes and cooled. The crystals formed were filtered, washed and dried to obtain N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-1,3-dimethyl-5-methoxycarbonylpyrazole-4-sulfonamide melting at 195.degree.-198.degree. C.
EXAMPLE 3
Synthesis of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1,3-dimethyl-5-propenyloxycarbonylpyrazole-4-sulfonamide (Compound No. 425):
Into a mixture of 17.4 ml of methanol and 8.7 g of 10 % aqueous sodium hydroxide was added 3.3 g (0.00864 mol) of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]1,3-dimethyl-5-methoxycarbonylpyrazole-4-sulfonamide (Compound No. 384), and the resultant mixture was refluxed for 45 minutes. After the reaction, the reaction mixture was made acidic with conc. hydrochloric acid to obtain 2.3 g of a hydrolyzed compound (Compound No. 435). The above compound was taken out in an amount of 1.5 g (0.00408 mol), dissolved in 8 ml of THF and 0.416 g of triethylamine was added to the resultant solution. After stirring for 10 minutes, a solution of 0.493 g of allyl bromide in 8 ml of THF was added and the mixture was refluxed for 3 hours. The precipitated salt was filtered off and the filtrate was evaporated to obtain 0.5 g of the crystals of the title compound. m.p. 180.degree.-183.degree. C.,
EXAMPLE 4
Synthesis of N-[(4.6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,3-dimethyl-5-dimethylcarbamoylpyrazole-4-sulfonamide (Compound No. 484):
In 15 ml of dry acetonitrile, there were added 1.97 g example 21 and 1.68 g (0.0088 mol) of dichloro-S-triazinyl isocyanate, and the mixture was refluxed for one hour. The reaction mixture was then left to stand at room temperature to give 2.2 g of crystals of N4,6-dichloro-1,3,5-triazin-2-yl)aminocarbonyl]-1,3-dimethyl-5-dimethylcarbamoylpyrazole-4-sulfonamide. m.p.182.degree.-185.degree. C.
Then, the above compound was taken out in an amount of 1.3 g (0.00297 mol) and added into 12 ml of methanol. Into this mixture, there were added portonwise sodium methoxide prepared from 0.205 g of sodium and 5 ml of methanol. After the reaction, the mixture was filtered and methanol was evaporated. The residue was dissolved in ice-water and made acidic with hydrochloride acid, whereby 0.8 g of the crystals of the title compound was obtained. m.p. 170.degree.-175.degree. C.,
EXAMPLE 5
Synthesis of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-dimethyl-5-dimethylsulfamoylpyrazole-4-sulfonamide (Compound No. 596):
With the use of 39 g (0.186 mol) of the sulfonamide obtained in Reference example 16, following the procedure as in Example 1, there was prepared 57.6 g N-(n-butylcarbamoyl)-1,3-dimethyl-5-chloropyrazole-4-sulfonamide. m.p. 188.degree. C.,
As the next step, 4.7 g of 55% sodium hydride was added to 100 ml of dimethylformamide and 9.1 g (0.074 mol) of benzylmercaptan was added to the mixture, followed by portionwise addition of 15 g (0.049 g) of the sulfonamide as prepared above. After stirring at room temperature for several hours, the reaction mixture was further stirred at 70 to 80 .degree. C. for 5 hours. After evaporation of the solvent, the residue was added into ice-water and the insolubles were filtered off. The filtrate was made acidic with hydrochloric acid to precipitate 19 g of N-(n-butyl-carbamoyl)1,3-dimethyl-5-benzylthiopyrazole-4-sulfonamide. Then, into a solution of 19 g (0.0479 mol) of the above compound dissolved in 100 ml of acetic acid, chlorine was passed at 10.degree. to 20.degree. C. for 1.5 hours. After the reaction, the reaction mixture was poured into ice-water to precipitate N-(n-butylcarbamoyl)-1,3-dimethyl-5 -chlorosulfonyl-4-sulfonamide. Subsequently, into a solution of 8.6 g of dimethylamine in 50 ml of THF, the above compound was added and the mixture was stirred at room temperature for 3 hours. After the reaction, THF was evaporated, and the residue was dissolved in an aqueous potassium carbonate solution. After removal of the insolubles, the residual solution was made acidic with hydrochoric acid to precipitate 10.0 g (0.026 mol) of N-(n-butylcarbamcyl)1,3-dimethyl-5-dimethylsulfamoyl-4-sulfonamide. m.p. 163.degree.-164.degree. C.
From the compound as prepared above, following the procedures of Examples 1 and 2, there was synthesized 1,3-dimethyl-5-dimethylsulfamoylpyrazole-4-sulfonyl isocyanate, which was in turn allowed to react with 2-amino-4-methoxy-6-methylpyrimidine to obtain the title compound. m.p. 215.degree.-217.degree. C.,
EXAMPLE 6
Synthesis of N-[(4,6-dimethyylpyrimidin-2-yl)aminocarbonyl]-1,3-dimethyl-5-ethylthiopyrazole-4-sulfonamide: (Compound No.742)
Into 10 ml of dimethylformamide, there were added 1.5 g (0.0042 mol) of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1,3-dimethyl-5-chloropyrazole-4-sulfonamide (Compound No. 85), 0.4 g of ethylmercaptan and 0.67 g of sodium hydroxide, and the resultant mixture was stirred at 60 to 70 .degree. C. for 4 hours. After the reaction, the solvent was evaporated, and the residue was added into ice-water, followed by acidification with hydrochloric acid, to precipitate 1.2 g of the crystals of the title compound. m.p. 189.degree.-190.degree. C.,
EXAMPLE 7
Synthesis of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide (Compound No. 835):
To a mixture of 5.0 g of4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide(Reference example 25), 4.45 g of dry potassium carbonate and 50 ml of acetone was added 2.13 g of n-butyl isocyanate at room temperature, and the mixture was stirred under reflux for 3 hours. After the reaction, acetone was evaporated under reduced pressure, and ice-water was added to the residue, followed by filtration of the insolubles. The filtrate was made acidic with hydrochloric acid and the crystals precipitated were filtered, washed with water and dried to give 5.1 g of N-(n-butylcarbamoyl)-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide melting at 117.degree.-119.degree. C. Then, this product was added into 120 ml of dry toluene, and 9.1 g of phosgene was passed into the mixture under reflux, followed further by refluxing for 1.5 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain crude sulfonyl isocyanate.
The above crude sulfonyl isocyanate (0.98 g) was added to a solution of 0.4 g of 2-amino-4,6-dimethoxy pyrimidine in 20 ml of dry acetonitrile and the mixture was stirred at room temperature. The crystals formed were filtered, washed and dried to obtain 0.8 g of the title compound melting at 170.degree.-172.degree. C.
EXAMPLE 8
Synthesis of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide (Compound No. 816):
With the use of the sulfonamide obtained in Reference example 26, following the procedure of Example 7, there was obtained N-(n-butylcarbamoyl)-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide. m.p. 88.degree.-90.degree. C.,
Further, following the procedure of Example 7, there was synthesized a sulfonyl isocyanate, which was further allowed to react with 2-amino-4-methoxy-6-methylpyrimidine to obtain the title compound melting at 183.degree.-184.degree. C.
EXAMPLE 9
Synthesis of N-[(4,6-dimethylpyrimdine-2-yl)aminocarbonyl]-4-chloro-1,3-dimethylpyrazole-5-sulfonamide (Compound No. 789):
(1) Synthesis of N-(ethoxycarbonyl)-4-chloro-1,3-dimethylpyrazole-5-sulfonamide
A mixture of 2.1 g (0.01 mol) of the sulfonamide obtained in Reference example 27, 1.41 g (0.013 mol) of ethyl chloroformate and 1.73 g (0.0125 mol) of potassium carbonate in 30 ml of dry acetone was stirred at room temperature for 18 hours. After the reaction, acetone was evaporated under reduced pressure and the residue was dissolved in water. The resultant solution was made acidic with conc. hydrochloric acid and extracted with ether. After evaporation of ether, the precipitated solids were recrystallized from a mixture of benzene and n-hexane to obtain 2.0 g of the title compound. m.p. 106 -109.degree. C.
(2) Synthesis of N-[(4,6-dimethylpyrimidine-2-yl)aminocarbonyl]-4-chloro-1,3-dimethylpyrazole-5-sulfonamide
Into 1.41 g (0.005 ml) of the compound obtained above in 10 ml of xylene was added 0.74 g (0.006 ml) of 2-amino-4,6-dimethylpyrimidine and the reaction mixture was refluxed for 2 hours. The resultant mixture was left to stand at room temperature to give 1.2 g of the title compound. m.p. 191.degree.-194.degree. C.
EXAMPLE 10
Synthesis of [(4-methoxy-6-methylpyrimidine-2-yl)aminocarbonyl]-1-methylpyrazole-3-sulfonamide (Compound No. 936) ;
With the use of the sulfonamide obtained in Reference example 30, following the procedure of Example 7, there was obtained N-(n-butylcarbamoyl)-1-methylpyrazole3-sulfonamide. m.p. 168 -169.degree. C.
Further, following the procedure of Example 7, there was synthesized a sulfonyl isocyanate, which was further allowed to react with 2-amino-4-methoxy-6-methylpyrimidin to obtain the title compound. m.p. 185.degree.-186.degree. C.
Next, similarly as in the above Examples, specific compounds were prepared and they are shown together with the compounds synthesized in Examples 1 to 10 in Table 4.
TABLE 4______________________________________Comp. No. m.p. (.degree.C.) Status______________________________________ 1 211.about.214 white crystal 2 201.about.203 " 3 171.about.172 " 4 180.about.181 " 5 173.about.174 " 6 115.about.120 " 7 171.about.175 " 8 177.about.179 " 9 174.about.176 " 10 163.about.166 " 11 187.about.190 " 12 183.about.184 " 13 219.about.220 " 14 210.about.211 " 15 181.about.183 " 16 202.about.203 " 17 180.about.182 " 18 180.about.182 " 19 202.about.203 " 20 213.about.214 " 21 222.about.224 " 22 226 " 85 212.about.217 " 86 192.about.196 " 87 184.about.188 " 88 148.about.152 " 89 153.about.157 "110 199.about.202 "111 178.about.181 "112 183.about.186 "113 220.about.227 "114 164.about.165 "138 242.about.244 "139 232.about.234 "140 210.about.214 "141 190.about.193 "142 190.about.195 "146 242.about.244 "147 216.about.218 "148 221.about.223 "150 242.about.245 "159 163.about.166 "160 198.about.200 "161 201.about.203 "162 208.about.210 "165 212.about.215 "166 219.about.220 "177 197.about.199 "178 207.about.209 "179 191.about.193 "291 189.about.192 "292 183.about.184 "293 148.about.149 "294 158.about.161 "295 174.about.175 "304 230.about.232 "305 206.about.208 "306 202.about.204 "307 185.about.195 "308 185.about.188 "316 203.about.205 "317 220.about.225 "320 194.about.196 "324 202.about.203 "325 187.about.188 "327 191.about.194 "328 184.about.186 "356 182.about.183 "357 163.about.164 "358 176.about.178 "359 158.about.165 "360 167.about.169 "361 169.about.171 "384 195.about.198 "385 187.about.190 "386 182.about.183 "387 195.about.198 "388 173.about.176 "391 209.about.211 "403 185.about.188 "409 186 "410 180.about.183 "411 175.about.180 "565 179.about.180 "566 178.about.179 "567 182.about.183 "568 145.about.147 "569 132.about.133 "570 170.about.171 "571 204.about.206 "572 183.about.184 "573 163.about.165 "580 185.about.186 "581 178.about.179 "210 182.about.185 "211 177.about.178 "228 195.about.199 "389 194.about.195 "390 192.about.193 "392 198.about.201 "394 205.about.207 "396 142.about.146 "399 178.about.181 "425 180.about.183 "435 189.about.192 "441 196.about.199 "442 182.about.184 "443 178.about.180 "444 183.about.185 "445 175.about.178 "463 162.about.164 "465 166.about.169 "484 170.about.175 "545 185.about.187 "546 166.about.169 "595 227.about.230 "596 215.about.217 "597 203.about.205 "598 209.about.211 "599 189.about.191 "600 221.about.223 "601 229.about.230 "602 252.about.254 "717 216.about.219 "718 205.about.208 "719 202.about.205 "720 188.about.190 "721 192.about.194 "727 174.about.177 "728 194.about.197 "729 199.about.201 "730 174.about.177 "731 192.about.195 "733 180.about.183 "734 179.about.181 "735 198.about.200 "737 140.about.142 "739 195.about.198 "740 216.about.219 "741 199.about.203 "742 189.about.190 "750 173.about.176 "766 190.about.193 "768 167.about.170 "775 184.about.187 "776 160.about.162 "778 162.about.165 "789 191.about.194 "790 165.about.168 "791 176.about.178 "792 158.about.160 "793 180.about.183 "799 194.about.195 "800 212.about.213 "801 166.about.168 "802 170.about.171 "803 198.about.200 "815 196.about.198 "816 183.about.184 "817 110.about.113 "818 171.about.172 "819 163.about.165 "833 163.about.165 "834 152.about.154 "835 170.about.172 "836 138.about.139 "837 142.about.144 "879 212.about.215 "880 206.about.209 "881 169.about.172 "882 175.about.177 "883 190.about.193 "884 193.about.195 "925 178.about.180 "926 173.about.176 "927 200.about.201 "928 156.about.158 "929 218.about.220 "930 220.about.222 "931 189.about.191 "932 205.about.207 "933 218.about.220 "934 213.about.216 "935 212.about.215 "936 185.about.186 "937 182.about.183 "938 176.about.180 "939 181.about.184 "940 182.about.184 "941 195.about.197 "942 211.about.213 "943 197.about.200 "______________________________________
In application of the compounds of this invention as herbicides, they can be applied by mixing with solid carriers, including for example clay, talc, bentonite, diatomaceous earth and others or liquid carriers, including for example water, alcohols (methanol, ethanol and the like), aromatic hydrocarbons (benzene, toluene, xylene and the like), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.), acid amides and others. They can be provided for practical use with addition of any desired additive selected from a emulsifier, a dispersing agent, a suspending agent, a wetting agent, a spreader and a stablizer and in any desired form such as a soluble concentrate, an emulsifiable concentrate, a wettable powder, a dust, a granule, a suspension concentrate, etc.
In the following, there are shown examples of formulations of herbicides containing the compounds of this invention as active ingredients, but they are not limitaive of this invention. In the exemplary formulations shown below, "parts" mean "parts by weight".
Exemplary formulation 1: Wettable powder
______________________________________Compound No. 2 of this invention 50 partsZiegleit A 46 parts(kaolin type clay: produced by ZiegleitKogyo Co., Ltd.)Solpol 5039 2 parts(mixture of nonionic surfactant and anionicsurfactant; trade name; produced by Toho KagakuCo., Ltd.)Carplex (anticaking agent) 2 parts(white carbon; trade name, produced by ShionogiSeiyaku Co., Ltd.)______________________________________
All of the above components are mixed and pulverized homogeneously to prepare a wettable powder In use, the above wettable powder is diluted with water to 50 to 50,000 times, and sprayed in an amount of the active ingredient of 0.0005 kg to 10 kg per hectare.
Exemplary formulation 2: Wettable powder
______________________________________Compound No. 86 of this invention 75 partsZiegleit A 19 parts(kaolin type clay: produced by ZiegleitKogyo Co., Ltd.)Solpol 5039 2 parts(mixture of nonionic surfactant and anionicsurfactant; trade name; produced by Toho KagakuCo., Ltd.)Carplex (anticaking agent) 4 parts(white carbon; trade name, produced by ShionogiSeiyaku Co., Ltd.)______________________________________
The above components are mixed and pulverized homogeneously to prepare a wettable powder.
Exemplary formulation 3: Wettable powder
______________________________________Compound No. 140 of this invention 50 partsZiegleit A 46 parts(kaolin type clay: produced by ZiegleitKogyo Co., Ltd.)Solpol 5039 2 parts(mixture of nonionic surfactant and anionicsurfactant; trade name; produced by Toho KagakuCo., Ltd.)Carplex (anticaking agent) 2 parts(white carbon; trade name, produced by ShionogiSeiyaku Co., Ltd.)______________________________________
The above components are mixed and pulverized homogeneously to prepare a wettable powder.
Exemplary formulation 4: Wettable powder
______________________________________Compound No. 159 of this invention 50 partsZiegleit A 46 parts(kaolin type clay: produced by ZiegleitKogyo Co., Ltd.)Solpol 5039 2 parts(mixture of nonionic surfactant and anionicsurfactant; trade name; produced by Toho KagakuCo., Ltd.)Carplex (anticaking agent) 2 parts(white carbon; trade name, produced by ShionogiSeiyaku Co., Ltd.)______________________________________
The above components are mixed and pulverized homogeneously to prepare a wettable powder.
Exemplary formulation 5: Wettable powder
______________________________________Compound No. 292 of this invention 25 partsZiegleit A 71 parts(kaolin type clay: produced by ZiegleitKogyo Co., Ltd.)Solpol 5039 2 parts(mixture of nonionic surfactant and anionicsurfactant; trade name; produced by Toho KagakuCo., Ltd.)Carplex (anticaking agent) 2 parts(white carbon; trade name, produced by ShionogiSeiyaku Co., Ltd.)______________________________________
The above components are mixed and pulverized homogeneously to prepare a wettable powder.
Exemplary formulation 6: Wettable powder
______________________________________Compound No. 384 of this invention 50 partsZiegleit A 44 parts(kaolin type clay: produced by ZiegleitKogyo Co., Ltd.)Solpol 5039 4 parts(mixture of nonionic surfactant and anionicsurfactant; trade name; produced by Toho KagakuCo., Ltd.)Carplex (anticaking agent) 2 parts(white carbon; trade name, produced by ShionogiSeiyaku Co., Ltd.)______________________________________
The above components are mixed and pulverized homogeneously to prepare a wettable powder.
Exemplary formulation 7: Wettable powder
______________________________________Compound No. 387 of this invention 45 partsZiegleit A 51 parts(kaolin type clay: produced by ZiegleitKogyo Co., Ltd.)Solpol 5039 2 parts(mixture of nonionic surfactant and anionicsurfactant; trade name; produced by Toho KagakuCo., Ltd.)Carplex (anticaking agent) 2 parts(white carbon; trade name, produced by ShionogiSeiyaku Co., Ltd.)______________________________________
The above components are mixed and pulverized homogeneously to prepare a wettable powder.
Exemplary formulation 8: Emulsifiable concentrate
______________________________________Compound No. 817 of this invention 2 partsXylene 78 partsDimethylformamide 15 partsSolpol 2680 5 parts(mixture of nonionic surfactant and anionicsurfactant; trade name; produced by Toho KagakuCo., Ltd.)______________________________________
The above components are homogeneously mixed to prepare an emulsifiable concentrate. In use, the above emulsifiable concentrate is diluted to 10 to 10,000 times and sprayed in an amount of the active ingredient of 0.0005 to 10 kg per hectare.
Exemplary formulation 9: Suspension concentrate
______________________________________Compound No. 387 of this invention 25 partsAgrisol S-710 10 parts(nonionic surfactant; trade name; produced by Kao-Atlas Co., Ltd.)Runox 1000 C 0.5 parts(anionic surfactant; trade name; produced by TohoKagaku Co., Ltd.)1% Rodopol water 20 parts(thickener; trade name; produced by RohnePoulainc)______________________________________
The above components are mixed to provide a suspnsion concentrate preparation.
Exemplary formulation 10: Granule
______________________________________Compound No. 816 of this invention 0.1 partsBentonite 55 partsTalc 44.9 parts______________________________________
All of the above components are mixed and pulverized homogeneously, then a little amount of water is added and the whole is stirred, kneaded and granulated by excluding granulator, then dried to prepare a granule.
Exemplary formulation 11: Granule
______________________________________Compound No. 817 of this invention 0.25 partsBentonite 55 partsTalc 44.57 parts______________________________________
All of the above components are mixed and pulverized homogenerously, then a little amount of water is added and the whole is stirred, kneaded and granulated by excluding granulator, then dried to prepare a granule.
Exemplary formulation 12: Granule
______________________________________Compound No. 834 of this invention 0.5 partsBentonite 55 partsTalc 44.5 parts______________________________________
All of the above components are mixed and pulverized homogenerously, hen a little amount of water is added and the whole is stirred, kneaded and granulated by excluding granulator, then dried to prepre a granule.
Exemplary formulation 13: Granule
______________________________________Compound No. 835 of this invention 1 partBentonite 55 partsTalc 44 parts______________________________________
All of the above components are mixed and pulverized homogeneously, then a little amount of water is added and the whole is stirred, kneaded and granulated by excluding granulator, then dried to prepare a granule.
If desired, the compound of this invention can be applied as a mixture with other kinds of herbicides, various insecticides, sterilizers or adjuvants during preparation or spraying.
As the other kinds of herbicides as mentioned above, there may be included those as described in Farm Chemicals Handbook, 69 th edition (1983).
The compounds of this invention can also be applied, in addition to the agricultural and horticultural fields such as farm fields, paddy fields, fruit gardens and the like, to athletic grounds, vacant lands, belts along the railroads and others. The amounts of the pesticide to be applied, which may differ depending on the scenes to be applied, the time of application, the application method, the kinds of the objective grasses and the crops harvested, may generally range suitably from 0.005 to 10 kg per hectare.
The following test examples are set forth for illustration of the utility of the compounds of this invention as herbicides.
Test example 1: Herbicidal effect test by soil treatment
In a plastic box of 15 cm length, 22 cm width and 6 cm depth, there was placed a deluvium soil, seeds of (A) rice (Oryza sativa), (B) barnyardgrass (Echinochloa crusgalli), (C) large crabgrass (Digitaria adscendens), (D) annual sedge (Cyperus microiria), (E) lambsquarters (Chenopodium ficifolium), (F) common purslane (Portulaca cleracea), (G) hairly galinosoga (Galinosoga ciliata), and (H) yellow cress (Rorippa atrovirens) were sown mixedly. After covering soil to about 1.5 cm over the seeds, herbicides were sprayed evenly on the soil surface to predetermined proportions of the active ingredient. In spraying, the wettable powder as shown in the foregoing exemplary formulations was diluted with water and sprayed over the entire surface by means of a small sprayer. Four weeks after spraying, the herbicidal effect on rice and the various weeds were examined according to the judgement criteria shown below. The results are shown in Table 5.
Judgement criteria:
______________________________________5 . . . Growth control rates of more than 90% (almost completely withered)4 . . . Growth control rates of 70 to 90%3 . . . Growth control rates of 40 to 70%2 . . . Growth control rates of 20 to 40%1 . . . Growth control rates of 5 to 20%0 . . . Growth control rates of less than 5% (substantially no effect)______________________________________
The above growth control rates are determined by measuring the top fresh weights of the treated plants and those of the non-treated plants, and calculated from the following formula: ##EQU1##
TABLE 5__________________________________________________________________________ Amount of active ingredientComp. appliedNo. (kg/ha) (A) (B) (C) (D) (E) (F) (G) (H)__________________________________________________________________________ 2 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 3 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 4 4 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 4 85 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 86 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 87 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 88 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5111 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5139 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5140 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5141 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5159 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 0.02 5 5 5 5 5 5 5 5292 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5293 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 3294 0.16 5 5 5 5 5 5 5 2 0.08 5 5 5 5 5 5 5 1384 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 0.02 5 5 5 5 5 5 5 5385 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 0.02 5 5 5 5 5 5 5 5386 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 0.02 5 5 5 5 5 5 5 5387 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 0.02 5 5 5 5 5 5 5 5388 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 0.02 5 5 5 5 5 5 5 5409 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 0.02 5 5 5 5 5 5 5 5410 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 0.02 5 5 5 5 5 5 5 5411 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5392 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5394 0.16 5 5 5 5 5 5 5 5396 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5425 0.16 5 5 5 5 5 5 5 5 0.08 4 5 5 5 5 5 5 5442 0.16 5 5 5 5 5 5 5 5 0.08 4 5 5 5 5 5 5 5443 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5444 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5445 0.16 5 5 5 5 5 2 5 5 0.08 5 5 5 5 5 4 5 5463 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5465 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5546 0.16 5 5 5 5 5 5 5 5595 0.16 5 5 5 5 5 5 5 5596 0.16 5 5 5 5 5 5 5 5597 0.16 5 5 5 5 5 5 5 5598 0.16 5 5 5 5 5 5 5 5599 0.16 5 5 5 5 5 5 5 5600 0.16 5 5 5 5 5 5 5 5601 0.16 5 5 5 5 5 5 5 5734 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5735 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5737 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5815 0.16 5 5 5 5 5 5 5 5 0.08 4 4 4 5 4 4 4 4816 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5817 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5818 0.16 5 5 5 5 5 5 5 5 0.08 5 5 4 5 5 5 5 5819 0.16 5 5 5 5 5 4 5 4 0.08 5 4 5 5 4 4 5 4833 0.16 5 5 5 5 5 5 5 5 0.08 4 4 4 5 4 4 4 4834 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5835 0.16 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5836 0.16 5 5 5 5 5 5 5 5 0.08 5 4 4 5 4 5 5 5837 0.16 5 5 5 5 5 4 5 5 0.08 5 4 5 5 4 3 4 4Control 0.16 3 2 2 4 3 2 2 3Compound 0.08 2 0 1 4 1 1 1 3Control 0.16 4 4 3 3 4 3 4 4Compound 0.08 3 3 3 1 3 2 3 3BControl 0.16 3 2 2 4 3 2 2 3Compound 0.08 2 1 1 2 1 1 1 2CControl 0.16 5 4 4 4 3 3 3 4Compound 0.08 4 3 4 3 3 3 3 3D__________________________________________________________________________
Control Compounds in the above Table 5 are as follows:
Control Comp. B (disclosed in Japanese Unexamined Publn. No. 169688/1981): ##STR295##
Control Comp. A (disclosed in Japanese Unexamined Publn. No. 169688/1981): ##STR296##
Control Comp. C (disclosed in Japanese Unexamined Publn. No. 169688/1981): ##STR297##
Control Comp. D (disclosed in Japanese Unexamined Publn. No. 102577/1980): ##STR298##
Test example 2: Herbicidal effect test by stem-leaf treatment
In a plastic box of 15 cm length, 22 cm width and 6 cm depth, there was placed a deluvium soil, seeds of (A) rice (Oryza sativa), (C) large crabgrass (Digitaria adscendens), (D) annual sedge (Cyperus microiria), (E) lambsquarters (Chenopodium ficifolium), (G) hairly galinosoga (Galinosoga ciliata), (H) yellow cress (Rorippa atrovirens), (F) corn (Zea mays), (J) soybean (Glysine max), (K) wheat (Triticum vulgare), and (L) tomato (Lycopersicum esculentum) were sown in shapes of spots, respectively, followed by covering of soil to about 1.5 cm over the seeds. After respective plants have grown to the second and the third leaf stage, herbicides were sprayed evenly onto the stem-leaf portion at predetermined proportions of the active ingredient.
In spraying, the wettable powder as shown in the foregoing exemplary formulations was diluted with water and sprayed over the entire surface of the stem-leaf portions of various weeds by means of a small sprayer.
Four weeks after spraying, the herbicidal effect on rice and the various plants were examined according to the judgement criteria as shown in Test example 1. The results are shown in Table 6.
Some of the compounds of this invention have selectivities on some kinds of crops.
In the following Table 6, the Control Compounds A, B and D are the same as those in the foregoing Test example 1.
TABLE 6__________________________________________________________________________ Amount of active ingredientComp. appliedNo. (kg/ha) (A) (C) (D) (E) (G) (H) (I) (J) (K) (L)__________________________________________________________________________ 2 0.16 5 5 5 5 5 5 5 3 4 2 0.08 5 5 5 5 5 5 5 2 3 1 3 0.16 4 5 5 5 4 5 5 5 5 5 0.08 4 5 5 5 4 5 4 4 4 5 4 0.16 5 5 5 5 5 5 5 5 5 4 0.08 5 5 5 5 5 5 5 5 4 4 85 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 4 4 5 4 5 5 5 5 3 86 0.16 5 5 5 5 5 5 5 5 5 1 0.08 5 5 5 5 5 5 5 5 5 0 87 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 5 5 88 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 4 5 5 5 5111 0.16 5 5 5 5 5 5 5 5 5 4 0.08 5 5 5 4 4 5 4 4 4 3159 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 4 4 0.04 5 5 5 5 5 5 5 5 4 3293 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 4 5294 0.16 5 5 5 5 5 5 5 5 5 4 0.08 5 5 5 5 5 4 4 4 4 3384 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 5 5385 0.16 5 5 5 5 5 5 5 5 5 1 0.08 5 5 5 5 5 5 5 5 5 0 0.04 5 5 5 5 5 5 5 5 5 0386 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 5 5387 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 5 5388 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 5 5409 0.16 5 5 5 5 5 5 5 5 5 1 0.08 5 5 5 5 5 5 5 5 5 0 0.04 5 5 5 5 5 5 5 5 5 0410 0.16 5 5 5 5 5 5 5 5 5 2 0.08 5 5 5 5 5 5 5 5 5 1 0.04 5 5 5 5 5 5 5 5 5 0411 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 5 5392 0.16 4 5 5 5 5 3 4 0 4 5394 0.16 5 4 5 5 5 5 5 5 5 5396 0.16 5 5 5 5 5 5 5 5 5 5425 0.16 5 4 5 5 5 5 5 5 5 5442 0.16 5 5 5 5 5 5 5 5 5 0 0.08 4 5 5 5 5 4 5 5 4 0443 0.16 4 5 5 5 5 5 5 5 5 5 0.08 4 4 5 5 5 5 5 5 5 5444 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 4 5 5 5 5 5445 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 4 5 5 5 5463 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 5 5465 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 5 5 5 5 5 5 5 5 5 0.04 5 5 5 5 5 5 5 5 5 5546 0.16 5 5 5 5 5 5 5 5 5 5595 0.16 5 5 5 5 5 5 5 5 5 5596 0.16 5 5 5 5 5 5 5 5 5 3597 0.16 5 5 5 5 5 5 5 5 5 5598 0.16 5 5 5 5 5 5 5 5 5 5599 0.16 5 5 5 5 5 5 5 5 5 5600 0.16 5 4 5 5 5 5 5 5 5 5601 0.16 5 5 4 5 5 5 5 5 5 5734 0.16 5 5 5 5 5 5 5 5 5 5 0.08 5 4 5 4 5 4 4 5 5 5735 0.16 5 5 5 5 5 5 5 5 5 1 0.08 4 5 5 4 5 4 5 5 5 0737 0.16 5 5 5 5 5 5 5 5 5 0 0.08 5 5 5 4 5 4 5 5 5 0815 0.16 5 5 5 5 5 5 5 5 2 5 0.08 5 4 5 5 5 5 5 5 1 4816 0.16 5 5 5 5 5 5 5 5 4 5 0.08 5 4 5 5 5 5 5 5 3 5817 0.16 5 5 5 5 5 5 5 5 2 5 0.08 4 4 5 5 5 5 5 5 1 4818 0.16 5 4 5 5 5 5 5 5 2 3 0.08 4 3 5 5 5 5 5 5 0 1819 0.16 5 5 5 5 5 5 5 5 3 5 0.08 4 4 5 5 5 4 4 5 2 4833 0.16 5 4 5 5 5 5 5 5 2 5 0.08 5 3 5 5 5 5 5 5 1 4834 0.16 5 5 5 5 5 5 5 5 3 5 0.08 5 4 5 5 5 5 5 5 2 3835 0.16 5 4 5 5 5 5 5 5 2 4 0.08 4 3 5 5 5 5 5 5 1 2836 0.16 4 3 5 5 5 5 5 5 2 3 0.08 3 2 5 4 5 4 4 4 0 1837 0.16 5 3 5 5 5 5 5 5 2 5 0.08 4 3 5 4 5 4 4 4 1 4Control 0.16 4 4 4 4 4 4 4 4 4 2Compound 0.08 3 4 4 4 4 4 4 4 3 2Control 0.16 3 3 3 3 3 3 3 4 2 2Compound 0.08 3 2 2 3 3 2 3 3 1 2BControl 0.16 3 4 3 3 4 3 3 3 2 2Compound 0.08 3 3 3 3 3 3 3 2 2 2D__________________________________________________________________________
Test example 3: Herbicidal effect test under paddy condition
In a Wagner pot of 1/50 m.sup.2, there was placed an alluvial soil, water was put thereinto, soil and water were mingled and a paddy condition of 2 cm depth of the water was made. Seeds of (B) barnyardgrass (Echinochloa crus-galli), (M) ducksalad (Monochoria vaginalis), (N) false pimpernel (Lindernia procumbens), (O) toothcup (Rotala indica) and (P) bulrush (Scirpus hotarui) were sown mixedly therein and tuberns of (Q) arrowhead (Sagittaria pygmaea) and (R) perennial flat sedge (Cyperus serotinus) were placed thereon. Then, young rice plants of the 2.5 leaf stage were transplanted.
On the next day, the diluted solution containing the compound of this invention was dropped on the water surface in predetermined proportions of the active ingredient.
Three weeks after application, the herbicidal effect on rice and the various weeds were examined according to the judgement criteria as shown in Test Example 1. The results are shown in Table 7.
TABLE 7__________________________________________________________________________ Amount of active ingredientCompound appliedNo. (kg/ha) (A) (B) (M) (N) (O) (P) (Q) (R)__________________________________________________________________________816 0.04 0 5 5 5 5 5 5 5 0.02 0 5 5 5 5 5 5 5 0.01 0 4 5 5 5 5 5 5817 0.04 0 5 5 5 5 5 5 5 0.02 0 5 5 5 5 5 5 5 0.01 0 4 5 5 5 5 5 5834 0.04 0 5 5 5 5 5 5 5 0.02 0 5 5 5 5 5 5 5 0.01 0 4 5 5 5 5 5 5835 0.04 0 5 5 5 5 5 5 5 0.02 0 5 5 5 5 5 5 5 0.01 0 4 5 5 5 5 5 5__________________________________________________________________________

Number	Date	Country	Kind
57-31377	Feb 1982	JPX
57-142069	Aug 1982	JPX

Number	Name	Date
4017298	Cross et al.	Apr 1977
4146726	Konotsune et al.	Mar 1979
4261729	Konotsune et al.	Apr 1981
4301293	Konotsune et al.	Nov 1981
4368067	Budzinski et al.	Jan 1983
4369058	Levitt	Jan 1983
4425151	Sturm et al.	Jan 1984

Number	Date	Country
58-670	Jan 1982	JPX
2276	Jan 1982	JPX

Pyrazolesulfonylurea derivatives, preparation thereof, herbicide containing said derivative as active ingredient and herbicidal method by use thereof

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