Condensed heterocyclic derivatives and herbicides

Abstract

A condensed heterocyclic derivative of the formula ##STR1## (wherein R is a hydroxyl group, R.sup.3 or R.sup.4 is an alkoxy group, W is an oxygen atom, Yn is a hydrogen atom, Z is a methine group, and A is a 5- or 6-membered heterocyclic ring which may be substituted, and a herbicide, are presented. When used for paddy field treatment, upland soil treatment and foliage treatment, the condensed heterocyclic derivative of the present invention exhibits excellent herbicidal activities against gramineous and non-gramineous weeds without adversely affecting crop plants.

Description

TECHNICAL FIELD

The present invention relates to condensed heterocyclic derivatives and their salts as well as herbicides containing them as active ingredients, which can be applied to paddy fields, upland fields and non-agricultural fields.

BACKGROUND ART

The present inventors found that quinoline and naphthalene derivatives have herbicidal activities and disclosed specific examples in Japanese Unexamined Patent Publication No. 56469/1990. Further, Japanese Unexamined Patent Publication No. 121973/1990 discloses that aromatic carboxylic acid derivatives containing quinoline, naphthalene, benzofuran, thiophene or pyridine ring have herbicidal activities.

However, the above-mentioned publications disclose nothing about specific compounds relating to the condensed heterocyclic derivatives of the present invention. Further, these compounds are not necessarily satisfactory from the viewpoint of the herbicidal effects. A number of other herbicides have been developed and contributed to the saving of energy for agricultural operations and to the improvement of the productivity. However, in their practical use, such herbicides also have various problems with respect to the herbicidal effects and the safety to crop plants.

The present inventors have conducted an extensive research on condensed heterocyclic derivatives with an object to develop a compound which is excellent in the herbicidal activities without bringing about phytotoxicity to crop plants. As a result, it has been found that the compounds of the present invention which are pyrimidine or triazine derivatives bonded to a condensed heterocyclic ring exhibit excellent herbicidal activities against not only annual weeds but also perennial gramineous weeds, cyperaceous weeds and broad leaf weeds in the paddy field treatment, upland soil treatment and foliage treatment, and they are highly safe to crop plants. The present invention has been accomplished on the basis of this discovery.

DISCLOSURE OF THE INVENTION

Namely, the present invention relates to a condensed heterocyclic derivative of the formula (I): ##STR2## {wherein A is a heterocyclic ring of the formula ##STR3## R is a hydrogen atom, a hydroxyl group, an alkoxy group which may be substituted, a benzyloxy group which may be substituted, an aryloxy group which may be substituted, an alkylthio group which may be substituted, a benzylthio group which may be substituted, an arylthio group which may be substituted, an alkenyloxy group which may be substituted, an alkynyloxy group which may be substituted, an alkenylthio group which may be substituted, an alkynylthio group which may be substituted, an alkylideneaminoxy group, or a group of the formula --NR.sup.6 R.sup.7 (wherein each of R.sup.6 and R.sup.7 which may be the same or different, is a hydrogen atom, an alkyl group, an alkoxy group, a benzyl group, an aryl group which may be substituted, an alkylsulfonyl group, or an arylsulfonyl group which may be substituted, or R.sup.6 and R.sup.7 may, together with the nitrogen atom, form a ring which may contain a hetero atom), each of R.sup.1 and R.sup.2 which may be the same or different, is a hydrogen atom, a formyl group, an alkylcarbonyl group which may be substituted, a cycloalkylcarbonyl group, an arylcarbonyl group which may be substituted, a pyridylcarbonyl group which may be substituted, a carboxyl group, a group of the formula --CONR.sup.6 R.sup.7 (wherein R.sup.6 and R.sup.7 are as defined above), an alkylthiocarbonyl group which may be substituted, a cycloalkylthiocarbonyl group, an aryloxycarbonyl group which may be substituted, an alkoxycarbonyl group which may be substituted, a cycloalkyl group, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, an aryl group which may be substituted, a halogen atom, a benzyloxycarbonyl group which may be substituted, a benzylthiocarbonyl group which may be substituted, a cycloalkoxycarbonyl group, an arylthiocarbonyl group which may be substituted, an alkenyloxycarbonyl group which may be substituted, an alkynyloxycarbonyl group which may be substituted, an alkenylthiocarbonyl group which may be substituted, an alkynylthiocarbonyl group which may be substituted, an isopropylideneaminoxycarbonyl group, a nitro group, a cyano group, a halogenated carbonyl group, a group of the formula CR.sup.8 .dbd.N--R.sup.9 (wherein R.sup.8 is a hydrogen atom, an aryl group, or an alkyl group, and R.sup.9 is a hydroxyl group, an alkyl group, an aryl group which may be substituted, a benzyl group which may be substituted, a benzyloxy group which may be substituted, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a phenoxy group which may be substituted, an alkylamino group, a dialkylamino group, an arylamino group which may be substituted, or an arylsulfonylamino group which may be substituted), a group of the formula NR.sup.10 R.sup.11 (wherein each of R.sup.10 and R.sup.11 which may be the same or different, is a hydrogen atom, an alkyl group, an aryl group which may be substituted, a benzyl group which may be substituted, a formyl group, an alkylcarbonyl group which may be substituted, a cycloalkylcarbonyl group, an arylcarbonyl group which may be substituted, a pyridylcarbonyl group which may be substituted, an alkoxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group which may be substituted, a carbamoyl group, an alkylthiocarbonyl group or an arylthiocarbonyl group which may be substituted, or R.sup.10 and R.sup.11 may, together with the nitrogen atom, form a ring which may contain a hetero atom), a group of the formula N.dbd.CR.sup.12 R.sup.13 (wherein each of R.sup.12 and R.sup.13 which may be the same or different, is a hydrogen atom, an alkyl group, or an aryl group which may be substituted, or R.sup.12 and R.sup.13 may form a ring which may contain a hetero atom), each of R.sup.3 and R.sup.4 which may be the same or different, is a hydrogen atom, an alkoxy group which may be substituted, a halogen atom, an alkylamino group, a dialkylamino group, or an alkyl group which may be substituted, R.sup.5 is a hydrogen atom, an alkyl group which may be substituted, a formyl group, an alkylcarbonyl group which may be substituted, a cycloalkylcarbonyl group, an arylcarbonyl group which may be substituted, a pyridylcarbonyl group which may be substituted, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a benzyloxycarbonyl group, an alkylthiocarbonyl group, an arylthiocarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, a trialkylsilyl group, an alkenyl group, an alkynyl group, a 4,6-dimethoxypyridin-2-yl group, or trichloromethylthio group, each of X.sup.1 and X.sup.2 which may be the same or different, is an oxygen atom, a sulfur atom, a methylene group, a group of the formula NR.sup.14 (wherein R.sup.14 is a hydrogen atom or an alkyl group), a carbonyl group, a group of the formula C.dbd.NOR.sup.15 (wherein R.sup.15 is an alkyl group), or a hydroxymethylene group, Q.sup.1 is a methylene group, a carbonyl group, or a group of the formula C.dbd.C<R.sup.16 R.sup.17 (wherein each of R.sup.16 and R.sup.17 which may be the same or different, is a cyano group, a cycloalkylcarbonyl group, a benzoyl group, or an alkoxycarbonyl group), each of Q.sup.2 and Q.sup.3 which may be the same or different is a group of the formula C<R.sup.18 R.sup.19 �wherein each of R.sup.18 and R.sup.19 which may be the same or different, is a hydrogen atom, an alkyl group, or an alkoxycarbonyl group, or R.sup.18 and R.sup.19 together form a carbonyl group or a group of the formula C.dbd.CHR.sup.20 (wherein R.sup.20 is a hydrogen atom or an alkyl group)!, and each of a, b, d and e is a nitrogen atom or a methine group, provided that at least one of them is a nitrogen atom (provided that a case where each of a, b and d is a methine group and e is a nitrogen atom, and the formula (I) represents a 8-quinolinecarboxylic acid derivative, is excluded), Y is a halogen atom, an alkyl group which may be substituted, an alkoxy group, a phenyl group which may be substituted, a nitro group, an alkylamino group, or a dialkylamiono group, n is an integer of from 0 to 2, provided that when n is 2, it may represents a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group, a cyanomethylene group, and Z is a methine group or a nitrogen atom}, or its salt; and a herbicide containing it as an active ingredient.

As preferred compounds, among them, those of the formula (I) wherein R is a hydrogen atom, a hydroxyl group and a C.sub.1 -C.sub.6 alkoxy group, may, for example, be mentioned. R.sup.3 and R.sup.4 may, for example, be a halogen atom, which may be a chlorine, bromine, fluorine or iodine atom, a C.sub.1 -C.sub.6 alkyl group or an alkoxy group.

Further, R.sup.1 and R.sup.2 may, for example, be a C.sub.1 -C.sub.8 alkyl group, a formyl group, a C.sub.1 -C.sub.8 alkylcarbonyl group, a C.sub.1 -C.sub.8 alkoxycarbonyl group, a C.sub.1 -C.sub.8 alkylthiocarbonyl group, a C.sub.1 -C.sub.8 cycloalkoxycarbonyl group, a C.sub.1 -C.sub.8 cycloalkylthiocarbonyl group, a C.sub.3 -C.sub.6 alkenyloxycarbonyl group which may be substituted, a C.sub.3 -C.sub.6 alkenylthiocarbonyl group, a C.sub.3 -C.sub.6 alkynyloxycarbonyl group which may be substituted, or a C.sub.3 -C.sub.6 alkynylthiocarbonyl group, and R.sup.5 may, for example, be a hydrogen atom, a formyl group, or a C.sub.1 -C.sub.8 alkylcarbonyl group. Now, specific examples of the compound of the present invention will be shown in Tables 1 to 59. The compound numbers will be referred to in the subsequent description.

TABLE 1__________________________________________________________________________ ##STR4##Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________1 CH.sub.3 COOC.sub.2 H.sub.5 ##STR5## O O H CH 127-1312 CH.sub.3 COOC.sub.2 H.sub.5 OH O O H CH 160-1633 CH.sub.3 COOC.sub.2 H.sub.5 OCH.sub.3 O O H CH 132-133.54 CH.sub.3 COOC.sub.2 H.sub.5 ##STR6## O O H CH 92-935 CH.sub.3 COOC.sub.2 H.sub.5 NHSO.sub.2 CH.sub.3 O O H CH6 CH.sub.3 COOC.sub.2 H.sub.5 OCH.sub.2 COOC.sub.2 H.sub.5 O O H CH 92-94.57 CH.sub.3 COOC.sub.2 H.sub.5 OC.sub.2 H.sub.5 O O H CH 130-1318 CH.sub.3 COOC.sub.2 H.sub.5 ##STR7## O O H CH 106.5-1099 CH.sub.3 COOC.sub.2 H.sub.5 ##STR8## O O H CH 153-15710 CH.sub.3 COOC.sub.2 H.sub.5 ##STR9## O O H CH 130.5-13211 CH.sub.3 COOC.sub.2 H.sub.5 ##STR10## O O H CH 112.5-11412 CH.sub.3 COOC.sub.2 H.sub.5 OCH.sub.2 OC.sub.2 H.sub.5 O O H CH 113-11613 CH.sub.3 COOC.sub.2 H.sub.5 ##STR11## O O H CH 1.542914 CH.sub.3 COOC.sub.2 H.sub.5 OC.sub.3 H.sub.7 O O H CH 119-12115 CH.sub.3 COOC.sub.2 H.sub.5 OC.sub.3 H.sub.7 -i O O H CH 88.5-90__________________________________________________________________________ TABLE 2__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________16 CH.sub.3 COOC.sub.2 H.sub.5 ##STR12## O O H CH 146-14817 CH.sub.3 COOC.sub.2 H.sub.5 ##STR13## S O H CH18 CH.sub.3 COOC.sub.2 H.sub.5 OH S O H CH19 CH.sub.3 COOC.sub.2 H.sub.5 ##STR14## S O H CH20 CH.sub.3 COOC.sub.2 H.sub.4 C.sub.3 H.sub.7 -i ##STR15## O O H CH 141-14421 CH.sub.3 COOC.sub.2 H.sub.4 C.sub.3 H.sub.7 -i OH O O H CH 140.5-14322 CH.sub.3 COOC.sub.2 H.sub.4 C.sub.3 H.sub.7 -i ##STR16## O O H CH 1.531023 CH.sub.3 COOCH.sub.3 ##STR17## O O H CH 1.583924 CH.sub.3 COOCH.sub.3 OH O O H CH 174-17825 CH.sub.3 COOCH.sub.3 OCH.sub.3 O O H CH26 CH.sub.3 COOCH.sub.3 ##STR18## O O H CH 126-13027 CH.sub.3 COOCH.sub.3 OH S O H CH 219-223 654928 CH.sub.3 COOCH.sub.3 ##STR19## S O H CH29 CH.sub.3 COOCH.sub.3 ##STR20## S O H CH30 CH.sub.3 COOCH.sub.3 OH O O H N 182-185__________________________________________________________________________ TABLE 3__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________31 CH.sub.3 COOCH.sub.3 ##STR21## O O H N 88-9032 CH.sub.3 COOCH.sub.3 ##STR22## O O H N 120-12233 CH.sub.3 COOCH.sub.3 OH S O H N34 CH.sub.3 COOC.sub.3 H.sub.7 OH O O H CH 162-16635 CH.sub.3 COOC.sub.4 H.sub.9 -s OH O O H CH 144-147.536 CH.sub.3 COOC.sub.4 H.sub.9 OH O O H CH 160-16437 CH.sub.3 CONH.sub.2 OH O O H CH38 CH.sub.3 COOH OH O O H CH 186-18839 CH.sub.3 COCH.sub.3 ##STR23## O O H CH 62-6540 CH.sub.3 COCH.sub.3 OH O O H CH 166-16941 CH.sub.3 COCH.sub.3 OCH.sub.3 O O H CH 178-18142 CH.sub.3 COCH.sub.3 ##STR24## O O H CH 122-12543 CH.sub.3 COCH.sub.3 NHSO.sub.2 CH.sub.3 O O H CH44 CH.sub.3 ##STR25## OCH.sub.3 O O H CH 101-10345 CH.sub.3 ##STR26## ##STR27## O O H CH 1.577846 CH.sub.3 ##STR28## OH O O H CH47 CH.sub.3 ##STR29## ##STR30## O O H CH 120-12348 CH.sub.3 ##STR31## OH O O H CH 184-187__________________________________________________________________________ TABLE 4__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________49 CH.sub.3 ##STR32## OCH.sub.3 O O H CH 169-17250 CH.sub.3 ##STR33## ##STR34## O O H CH 115-11751 CH.sub.3 ##STR35## OCH.sub.3 O O H CH 133-13752 CH.sub.3 ##STR36## OCH.sub.2 OC.sub.2 H.sub.5 O O H CH 127-13053 CH.sub.3 ##STR37## OCH.sub.3 O O H CH 168-170.554 CH.sub.3 ##STR38## OH O O H CH55 CH.sub.3 ##STR39## OCH.sub.3 O O H CH 128-13156 CH.sub.3 ##STR40## OH O O H CH57 CH.sub.3 ##STR41## OCH.sub.3 O O H CH 170-173.558 CH.sub.3 ##STR42## OH O O H CH59 CH.sub.3 COC.sub.4 H.sub.9 -i OH O O H CH 168-17160 CH.sub.3 CN OH O O H CH 175-179__________________________________________________________________________ TABLE 5__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________61 H COOC.sub.2 H.sub.5 OH O O H CH 161-16362 H COOC.sub.2 H.sub.5 ##STR43## O O H CH 1.535163 H COOC.sub.2 H.sub.5 ##STR44## O O H CH 91.5-9364 H CN OH O O H CH65 H CN ##STR45## O O H CH66 H CN ##STR46## O O H CH67 CF.sub.3 COOCH.sub.3 OH O O H CH68 CH.sub.3 COC.sub.4 H.sub.9 -i ##STR47## O O H CH 1.576569 CF.sub.3 ##STR48## OCH.sub.3 O O H CH 155-15870 CF.sub.3 ##STR49## OH O O H CH 178-18171 C.sub.2 H.sub.5 COOC.sub.2 H.sub.5 OH O O H CH 159.5-16272 C.sub.2 H.sub.5 COOC.sub.2 H.sub.5 ##STR50## O O H CH 116-12073 C.sub.2 H.sub.5 COOC.sub.2 H.sub.5 ##STR51## O O H CH 1.533974 C.sub.2 H.sub.5 COOC.sub.3 H.sub.7 OH O O H CH 119-122__________________________________________________________________________ TABLE 6__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________75 C.sub.2 H.sub.5 COOC.sub.3 H.sub.7 ##STR52## O O H CH 108-109.576 C.sub.2 H.sub.5 COOC.sub.3 H.sub.7 -i OH O O H CH 137-14077 CF.sub.3 ##STR53## O.sup.- Na.sup.+ O O H CH >30078 CF.sub.3 ##STR54## ##STR55## O O H CH 143-14679 CH.sub.2 Cl COOC.sub.2 H.sub.5 OH O O H CH80 C.sub.2 H.sub.5 COOC.sub.3 H.sub.7 -i ##STR56## O O H CH 94-9681 CH.sub.2 Cl COOC.sub.2 H.sub.5 ##STR57## O O H CH82 ##STR58## COCH.sub.3 OCH.sub.3 O O H CH 151-154.583 ##STR59## COCH.sub.3 OH O O H CH84 ##STR60## ##STR61## ##STR62## O O H CH 176.5-18085 ##STR63## ##STR64## OH O O H CH 178.5-18186 ##STR65## ##STR66## ##STR67## O O H CH Unmeasurable__________________________________________________________________________ TABLE 7__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________87 ##STR68## COOC.sub.2 H.sub.5 ##STR69## O O H CH 85-9088 ##STR70## COOC.sub.2 H.sub.5 OH O O H CH 154-15889 ##STR71## COOC.sub.2 H.sub.5 ##STR72## O O H CH 1.573090 ##STR73## CN ##STR74## O O H CH 152-15691 ##STR75## CN OH O O H CH 165-16992 ##STR76## CN OCH.sub.3 O O H CH93 ##STR77## CN ##STR78## O O H CH 143-14694 ##STR79## ##STR80## OCH.sub.3 O O H CH 138-14095 ##STR81## ##STR82## OH O O H CH96 ##STR83## COCH.sub.3 OCH.sub.3 O O H CH 137-14197 ##STR84## COCH.sub.3 OH O O H CH__________________________________________________________________________ TABLE 8__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________ 98 CH.sub.3 COOC.sub.2 H.sub.5 OH O O 7-Cl CH 99 CH.sub.3 COOC.sub.2 H.sub.5 OH O O 7-CH.sub.3 CH100 CH.sub.3 COOC.sub.2 H.sub.5 OH O O 6-Cl CH101 CH.sub.3 COOC.sub.2 H.sub.5 OH O O 6-CH.sub.3 CH102 CH.sub.3 COOC.sub.2 H.sub.5 OH O O 7-OCH.sub.3 CH103 CH.sub.3 COOC.sub.2 H.sub.5 OH O O 6-N(CH.sub.3).sub.2 CH104 H CH.sub.3 H O S H CH 158-161105 H CH.sub.3 OH O S H CH 172-175106 H CH.sub.3 ##STR85## O S H CH107 H CH.sub.3 OCH.sub.3 O S H CH108 COOCH.sub.3 CH.sub.3 H O S H CH 201-206109 COOCH.sub.3 CH.sub.3 OH O S H CH 154-158.5110 COOCH.sub.3 CH.sub.3 ##STR86## O S H CH111 COOCH.sub.3 CH.sub.3 ##STR87## O S H CH112 CH.sub.3 COOCH.sub.3 OH O S H CH 153-155113 CH.sub.3 COOCH.sub.3 ##STR88## O S H CH114 CH.sub.3 COOCH.sub.3 OCH.sub.3 O S H CH115 CH.sub.3 COOCH.sub.3 ##STR89## O S H CH116 CH.sub.3 COOC.sub.2 H.sub.5 OH O S H CH 155-158117 H H OH O S H CH118 H H ##STR90## O S H CH__________________________________________________________________________ TABLE 9__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________119 H H ##STR91## O S H CH120 H H OCH.sub.3 O S H CH121 H H OH O S H N122 H CH.sub.3 OH O S H N123 H CH.sub.3 OH S S H CH124 H CH.sub.3 OH O NCH.sub.3 H CH125 H CH.sub.3 OH O NCH.sub.3 H N126 H CH.sub.3 OH S NCH.sub.3 H CH127 COOCH.sub.3 CH.sub.3 OH O NCH.sub.3 H CH128 CH.sub.3 COOCH.sub.3 ##STR92## O O H CH129 CH.sub.3 COOCH.sub.3 ##STR93## O O H N130 CH.sub.3 COOCH.sub.3 O.sup.- Na.sup.+ O O H CH >300131 CH.sub.3 COOC.sub.2 H.sub.5 ##STR94## O NH H CH 196-199132 CH.sub.3 COOC.sub.2 H.sub.5 OH O NH H CH 202-204133 H COCH.sub.3 OH O O H CH__________________________________________________________________________ TABLE 10__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________134 CH.sub.3 COOC.sub.2 H.sub.5 SCH.sub.3 O O H CH135 CH.sub.3 COOC.sub.2 H.sub.5 SC.sub.2 H.sub.5 O O H CH136 CH.sub.3 COOC.sub.2 H.sub.5 ##STR95## O O H CH137 CH.sub.3 COOC.sub.2 H.sub.5 OH N(CHO) O H CH138 CH.sub.3 COOC.sub.2 H.sub.5 OH CH.sub.2 O H CH139 CH.sub.3 COOC.sub.2 H.sub.5 OH CH(CN) O H CH140 CH.sub.3 COOCH.sub.3 NH.sub.2 O O H CH141 CH.sub.3 COOCH.sub.3 NHCH.sub.3 O O H CH142 CH.sub.3 COOC.sub.2 H.sub.5 N(CH.sub.3).sub.2 O O H CH143 COCH.sub.3 CH.sub.3 ##STR96## O O H CH144 COCH.sub.3 CH.sub.3 OH O O H CH145 COCH.sub.3 CH.sub.3 ##STR97## O O H CH146 CH.sub.3 ##STR98## ##STR99## O O H CH147 CH.sub.3 ##STR100## OH O O H CH 143-146148 CH.sub.3 ##STR101## ##STR102## O O H CH149 CH.sub.3 COSCH.sub.3 OCH.sub.2 CHCH.sub.2 O O H CH 134-136150 CH.sub.3 COSCH.sub.3 OH O O H CH 163-165151 CH.sub.3 COSCH.sub.3 ##STR103## O O H CH152 CH.sub.3 COSC.sub.2 H.sub.5 OCH.sub.2 CHCH.sub.2 O O H CH 102-105153 CH.sub.3 COSC.sub.2 H.sub.5 OH O O H CH 149-152__________________________________________________________________________ TABLE 11__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________154 CH.sub.3 COSC.sub.2 H.sub.5 ##STR104## O O H CH155 CH.sub.3 CONHCH.sub.3 OCH.sub.2 CHCH.sub.2 O O H CH156 CH.sub.3 CONHCH.sub.3 OH O O H CH157 CH.sub.3 CONHCH.sub.3 ##STR105## O O H CH158 CH.sub.3 CON(C.sub.2 H.sub.5).sub.2 OCH.sub.2 CHCH.sub.2 O O H CH 96-98159 CH.sub.3 CON(C.sub.2 H.sub.5).sub.2 OH O O H CH 183-186160 CH.sub.3 CON(C.sub.2 H.sub.5).sub.2 ##STR106## O O H CH161 CH.sub.3 ##STR107## OCH.sub.2 CHCH.sub.2 O O H CH 85-88162 CH.sub.3 ##STR108## OH O O H CH 180-182.5163 CH.sub.3 ##STR109## ##STR110## O O H CH164 CH.sub.3 COOC.sub.3 H.sub.7 ##STR111## O O H CH 132-136165 CH.sub.3 COOC.sub.3 H.sub.7 ##STR112## O O H CH 108-109166 CH.sub.3 COOC.sub.4 H.sub.9 ##STR113## O O H CH 135-136.5167 CH.sub.3 COOC.sub.4 H.sub.9 ##STR114## O O H CH 1.5209__________________________________________________________________________ TABLE 12__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________168 CH.sub.3 COOC.sub.4 H.sub.9 -s ##STR115## O O H CH 149-150.5169 CH.sub.3 COOC.sub.4 H.sub.9 -s ##STR116## O O H CH 90-91.5170 CH.sub.3 COOC.sub.4 H.sub.9 -i ##STR117## O O H CH 152-156171 CH.sub.3 COOC.sub.4 H.sub.9 -i OH O O H CH 135-138172 CH.sub.3 COOC.sub.4 H.sub.9 -i ##STR118## O O H CH 1.5276173 CH.sub.3 COOC.sub.4 H.sub.9 -t ##STR119## O O H CH 170-172174 CH.sub.3 COOC.sub.4 H.sub.9 -t OH O O H CH 153-157175 CH.sub.3 COOC.sub.4 H.sub.9 -t ##STR120## O O H CH176 CH.sub.3 COOC.sub.4 H.sub.9 -t OCH.sub.2 OC.sub.2 H.sub.5 O O H CH177 CH.sub.3 COOC.sub.5 H.sub.11 ##STR121## O O H CH 115-116.5178 CH.sub.3 COOC.sub.5 H.sub.11 OH O O H CH 140-144179 CH.sub.3 COOC.sub.5 H.sub.11 ##STR122## O O H CH 1.5291180 CH.sub.3 COOC.sub.5 H.sub.11 OCH.sub.2 OC.sub.2 H.sub.5 O O H CH181 CH.sub.3 COOC.sub.6 H.sub.13 ##STR123## O O H CH 99-101182 CH.sub.3 COOC.sub.6 H.sub.13 OH O O H CH 153-159__________________________________________________________________________ TABLE 13__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________183 CH.sub.3 COOC.sub.6 H.sub.13 ##STR124## O O H CH 1.5280184 CH.sub.3 COOC.sub.6 H.sub.13 OCH.sub.2 OC.sub.2 H.sub.5 O O H CH185 CH.sub.3 COOC.sub.7 H.sub.15 ##STR125## O O H CH 78-80186 CH.sub.3 COOC.sub.7 H.sub.15 OH O O H CH 145-149187 CH.sub.3 COOC.sub.7 H.sub.15 ##STR126## O O H CH 1.5288188 CH.sub.3 COOC.sub.7 H.sub.15 OCH.sub.2 OC.sub.2 H.sub.5 O O H CH189 CH.sub.3 COOC.sub.8 H.sub.17 ##STR127## O O H CH 105-108190 CH.sub.3 COOC.sub.8 H.sub.17 OH O O H CH 148-151191 CH.sub.3 COOC.sub.8 H.sub.17 ##STR128## O O H CH 1.5170192 CH.sub.3 ##STR129## ##STR130## O O H CH 99-101193 CH.sub.3 ##STR131## OH O O H CH 130-132194 CH.sub.3 ##STR132## ##STR133## O O H CH 1.5260195 CH.sub.3 ##STR134## OCH.sub.2 OC.sub.2 H.sub.5 O O H CH196 CH.sub.3 ##STR135## ##STR136## O O H CH197 CH.sub.3 ##STR137## OH O O H CH 115-119__________________________________________________________________________ TABLE 14__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________198 CH.sub.3 ##STR138## ##STR139## O O H CH199 CH.sub.3 ##STR140## OCH.sub.2 OC.sub.2 H.sub.5 O O H CH200 CH.sub.3 CONHC.sub.2 H.sub.5 ##STR141## O O H CH 147-149201 CH.sub.3 CONHC.sub.2 H.sub.5 OH O O H CH 200-203202 CH.sub.3 CONHC.sub.2 H.sub.5 OCH.sub.2 CCH.sub.2 O O H CH Unmeasurable203 CH.sub.3 COOC.sub.3 H.sub.7 -i ##STR142## O O H CH 140-143204 CH.sub.3 COOC.sub.3 H.sub.7 -i OH O O H CH 167-170205 CH.sub.3 COOC.sub.3 H.sub.7 -i ##STR143## O O H CH Unmeasurable206 CH.sub.3 COOC.sub.3 H.sub.7 -i ##STR144## O O H CH207 CH.sub.3 COOC.sub.3 H.sub.7 -i OCH.sub.2 OC.sub.2 H.sub.5 O O H CH208 CH.sub.3 COOC.sub.3 H.sub.7 -i O.sup.- Na.sup.+ O O H CH 208-210209 CH.sub.3 COOC.sub.3 H.sub.7 -i ##STR145## O O H CH210 CH.sub.3 ##STR146## ##STR147## O O H CH 183-184.5211 CH.sub.3 ##STR148## OH O O H CH 161-164.5__________________________________________________________________________ TABLE 15__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________212 CH.sub.3 ##STR149## ##STR150## O O H CH213 CH.sub.3 ##STR151## ##STR152## O O H CH 194-196214 CH.sub.3 ##STR153## OH O O H CH 103-105215 CH.sub.3 ##STR154## ##STR155## O O H CH 1.5334216 CH.sub.3 ##STR156## OH O O H CH 142-144217 CH.sub.3 ##STR157## ##STR158## O O H CH218 CH.sub.3 COOCH.sub.2 CHCH.sub.2 ##STR159## O O H CH 101.5-104219 CH.sub.3 COOCH.sub.2 CHCH.sub.2 OH O O H CH 163-165220 CH.sub.3 COOCH.sub.2 CHCH.sub.2 ##STR160## O O H CH221 CH.sub.3 COOCH.sub.2 CHCH.sub.2 ##STR161## O O H CH 1.5322222 CH.sub.3 COOCH.sub.2 CCH ##STR162## O O H CH223 CH.sub.3 COOCH.sub.2 CCH OH O O H CH 155-158224 CH.sub.3 COOCH.sub.2 CCH OCH.sub.2 CHCH.sub.2 O O H CH 93-95__________________________________________________________________________ TABLE 16__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________225 CH.sub.3 COOCH.sub.2 CCH ##STR163## O O H CH 70-73226 CH.sub.3 COSC.sub.3 H.sub.7 OCH.sub.2 CHCH.sub.2 O O H CH 77-79227 CH.sub.3 COSC.sub.3 H.sub.7 OH O O H CH 130-133228 CH.sub.3 COSC.sub.3 H.sub.7 ##STR164## O O H CH229 CH.sub.3 COSC.sub.3 H.sub.7 OCH.sub.2 OC.sub.2 H.sub.5 O O H CH230 CH.sub.3 COSC.sub.3 H.sub.7 -i OCH.sub.2 CHCH.sub.2 O O H CH 105-108231 CH.sub.3 COSC.sub.3 H.sub.7 -i OH O O H CH 160-163232 CH.sub.3 COSC.sub.5 H.sub.11 OCH.sub.2 CHCH.sub.2 O O H CH 1.5621233 CH.sub.3 COSC.sub.5 H.sub.11 OH O O H CH 132-134234 CH.sub.3 COSC.sub.4 H.sub.9 OCH.sub.2 CHCH.sub.2 O O H CH 1.5665235 CH.sub.3 COSC.sub.4 H.sub.9 OH O O H CH 127-130236 CH.sub.3 COSC.sub.4 H.sub.9 ##STR165## O O H CH 104-106237 CH.sub.3 COSC.sub.4 H.sub.9 -i OCH.sub.2 CHCH.sub.2 O O H CH 75-77238 CH.sub.3 COSC.sub.4 H.sub.9 -i OH O O H CH239 CH.sub.3 COSC.sub.4 H.sub.9 -i ##STR166## O O H CH240 CH.sub.3 COSC.sub.4 H.sub.9 -t OCH.sub.2 CHCH.sub.2 O O H CH241 CH.sub.3 COSC.sub.4 H.sub.9 -t OH O O H CH 126-128242 CH.sub.3 COSC.sub.4 H.sub.9 -t ##STR167## O O H CH243 CH.sub.3 ##STR168## OCH.sub.2 CHCH.sub.2 O O H CH244 CH.sub.3 ##STR169## OH O O H CH245 CH.sub.3 ##STR170## ##STR171## O O H CH__________________________________________________________________________ TABLE 17__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________246 CH.sub.3 CON(CH.sub.3).sub.2 ##STR172## O O H CH Unmeasurable247 CH.sub.3 CON(CH.sub.3).sub.2 OH O O H CH 185-187248 CH.sub.3 CON(CH.sub.3).sub.2 OCH.sub.2 CHCH.sub.2 O O H CH Unmeasurable249 CH.sub.3 ##STR173## ##STR174## O O H CH250 CH.sub.3 ##STR175## OH O O H CH 171-174251 CH.sub.3 ##STR176## ##STR177## O O H CH252 CH.sub.3 COOC.sub.2 H.sub.5 ##STR178## O O H CH253 CH.sub.3 COOC.sub.2 H.sub.5 ##STR179## O O H CH254 CH.sub.3 COCl OCH.sub.2 CHCH.sub.2 O O H CH 75-78255 CH.sub.3 COCl ##STR180## O O H CH 136-140256 Cl COOC.sub.2 H.sub.5 OH O O H CH257 COOC.sub.2 H.sub.5 Cl OH O O H CH258 CH.sub.3 ##STR181## OCH.sub.2 CHCH.sub.2 O O H CH 95-97259 CH.sub.3 ##STR182## OH O O H CH 144.5-147260 CH.sub.3 ##STR183## ##STR184## O O H CH__________________________________________________________________________ TABLE 18__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________261 CH.sub.3 COSCH.sub.2 CHCH.sub.2 ##STR185## O O H CH262 CH.sub.3 COSCH.sub.2 CHCH.sub.2 OH O O H CH 1.5786263 CH.sub.3 COSCH.sub.2 CHCH.sub.2 ##STR186## O O H CH264 CH.sub.3 COSCH.sub.2 CCH ##STR187## O O H CH265 CH.sub.3 COSCH.sub.2 CCH OH O O H CH266 CH.sub.3 COSCH.sub.2 CCH ##STR188## O O H CH267 C.sub.3 H.sub.7 COOC.sub.2 H.sub.5 ##STR189## O O H CH 102.5-105268 C.sub.3 H.sub.7 COOC.sub.2 H.sub.5 OH O O H CH 140.5-144269 C.sub.3 H.sub.7 COOC.sub.2 H.sub.5 ##STR190## O O H CH 1.5291270 C.sub.2 H.sub.5 COOCH.sub.3 ##STR191## O O H CH 115-117271 C.sub.2 H.sub.5 COOCH.sub.3 OH O O H CH 164-167272 C.sub.2 H.sub.5 COOH ##STR192## O O H CH 185-188273 C.sub.3 H.sub.7 -i COOC.sub.2 H.sub.5 OC.sub.2 H.sub.5 O O H CH 1.5459274 C.sub.3 H.sub.7 -i COOC.sub.2 H.sub.5 OH O O H CH 157-159275 C.sub.3 H.sub.7 -i COOC.sub.2 H.sub.5 ##STR193## O O H CH 1.5318276 C.sub.2 H.sub.5 COOC.sub.2 H.sub.5 OC.sub.2 H.sub.5 O O H CH 1.5490277 C.sub.3 H.sub.7 COOC.sub.2 H.sub.5 OC.sub.2 H.sub.5 O O H CH 1.5431__________________________________________________________________________ TABLE 19__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________278 CH.sub.3 COOC.sub.3 H.sub.6 Cl OH O O H CH 161-165279 CH.sub.3 COOC.sub.3 H.sub.6 Cl ##STR194## O O H CH 124-125280 CH.sub.3 COOC.sub.2 H.sub.4 F OH O O H CH 152-155281 CH.sub.3 COOC.sub.2 H.sub.4 F ##STR195## O O H CH 114-117282 CH.sub.3 COOC.sub.3 H.sub.6 Br ##STR196## O O H CH 124-127283 CH.sub.3 COOC.sub.3 H.sub.6 Br OH O O H CH284 CH.sub.3 ##STR197## OCH.sub.2 CCH.sub.2 O O H CH 138-140285 H COOCH.sub.3 ##STR198## O O H CH286 H COOCH.sub.3 OH O O H CH 150-153287 H COOCH.sub.3 ##STR199## O O H CH288 H COOC.sub.3 H.sub.7 ##STR200## O O H CH289 H COOC.sub.3 H.sub.7 OH O O H CH 158-161290 H COOC.sub.3 H.sub.7 ##STR201## O O H CH291 H COOC.sub.3 H.sub.7 -i ##STR202## O O H CH 80-82292 H COOC.sub.3 H.sub.7 -i OH O O H CH 140-143.5293 H COOC.sub.3 H.sub.7 -i ##STR203## O O H CH__________________________________________________________________________ TABLE 20__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________294 H COOC.sub.4 H.sub.9 ##STR204## O O H CH 82-84295 H COOC.sub.4 H.sub.9 OH O O H CH 134-137296 H COOC.sub.4 H.sub.9 ##STR205## O O H CH297 H COOC.sub.4 H.sub.9 -i ##STR206## O O H CH 95-98298 H COOC.sub.4 H.sub.9 -i OH O O H CH 140-144299 H COOC.sub.4 H.sub.9 -i ##STR207## O O H CH300 H COOC.sub.4 H.sub.9 -s ##STR208## O O H CH 91-93301 H COOC.sub.4 H.sub.9 -s OH O O H CH Unmeasurable302 H COOC.sub.4 H.sub.9 -s ##STR209## O O H CH303 H COOC.sub.4 H.sub.9 -t ##STR210## O O H CH304 H COOC.sub.4 H.sub.9 -t OH O O H CH305 H COOC.sub.4 H.sub.9 -t ##STR211## O O H CH306 H COOC.sub.5 H.sub.11 ##STR212## O O H CH 88-90307 H COOC.sub.5 H.sub.11 OH O O H CH 117-119308 H COOC.sub.5 H.sub.11 ##STR213## O O H CH__________________________________________________________________________ TABLE 21__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________309 H COOC.sub.6 H.sub.13 ##STR214## O O H CH310 H COOC.sub.6 H.sub.13 OH O O H CH311 H COOC.sub.6 H.sub.13 ##STR215## O O H CH312 H ##STR216## ##STR217## O O H CH313 H ##STR218## OH O O H CH314 H ##STR219## ##STR220## O O H CH315 CH.sub.3 CONHC.sub.3 H.sub.7 -i ##STR221## O O H CH Unmeasurable316 CH.sub.3 CONHC.sub.3 H.sub.7 -i OH O O H CH 173--176317 CH.sub.3 CONHC.sub.3 H.sub.7 -i OCH.sub.2 CHCH.sub.2 O O H CH 157-159.5318 CH.sub.3 ##STR222## OCH.sub.2 CHCH.sub.2 O O H CH 137-139319 CH.sub.3 ##STR223## OH O O H CH 137-138320 CH.sub.3 ##STR224## ##STR225## O O H CH321 CH.sub.3 COOCH.sub.2 C.sub.4 H.sub.9 -t ##STR226## O O H CH 162-165322 CH.sub.3 COOCH.sub.2 C.sub.4 H.sub.9 -t OH O O H CH 137-140323 CH.sub.3 COOCH.sub.2 C.sub.4 H.sub.9 -t ##STR227## O O H CH__________________________________________________________________________ TABLE 22__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________324 CH.sub.3 COOCH.sub.2 C.sub.4 H.sub.9 -t OCH.sub.2 OC.sub.2 H.sub.5 O O H CH325 CH.sub.3 ##STR228## ##STR229## O O H CH 149-151326 CH.sub.3 ##STR230## OH O O H CH 146-148327 CH.sub.3 ##STR231## ##STR232## O O H CH 1.5330328 CH.sub.3 ##STR233## OCH.sub.2 OC.sub.2 H.sub.5 O O H CH329 CH.sub.3 ##STR234## OH O O H CH 173-175330 CH.sub.3 COOC.sub.3 H.sub.7 O.sup.- Na.sup.+ O O H CH331 CH.sub.3 COOC.sub.3 H.sub.7 ##STR235## O O H CH332 CH.sub.3 COOC.sub.3 H.sub.7 OCH.sub.2 CHCH.sub.2 O O H CH333 CH.sub.3 COOC.sub.3 H.sub.7 ##STR236## O O H CH334 CH.sub.3 COOC.sub.3 H.sub.7 N(CH.sub.3).sub.2 O O H CH335 CH.sub.3 COOC.sub.3 H.sub.7 ##STR237## O O H CH336 CH.sub.3 ##STR238## ##STR239## O O H CH Unmeasurable337 CH.sub.3 ##STR240## OH O O H CH 138-143__________________________________________________________________________ TABLE 23__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________338 CH.sub.3 ##STR241## OH O O H CH339 CH.sub.3 COOCH.sub.2 OC.sub.2 H.sub.5 ##STR242## O O H CH 110-113340 CH.sub.3 COOCH.sub.2 OC.sub.2 H.sub.5 OH O O H CH 152-154341 CH.sub.3 COOC.sub.2 H.sub.4 SCH.sub.3 OH O O H CH 140-143342 CH.sub.3 COOC.sub.2 H.sub.4 SCH.sub.3 OCH.sub.2 CHCH.sub.2 O O H CH 64-66343 CH.sub.3 COOCH(CF.sub.3).sub.2 ##STR243## O O H CH 158-160.5344 CH.sub.3 COOCH(CF.sub.3).sub.2 OH O O H CH 137-140345 CH.sub.3 COOCH.sub.3 O.sup.- H.sub.3.sup.+ NCH(CH.sub.3).sub.2 O O H CH 133.5-137346 CH.sub.3 ##STR244## OH O O H CH 189-191347 CH.sub.3 COOC.sub.2 H.sub.4 OCH.sub.3 ##STR245## O O H CH 105-107348 CH.sub.3 COOC.sub.2 H.sub.4 OCH.sub.3 OH O O H CH 138-142349 CH.sub.3 COOC.sub.2 H.sub.4 OCH.sub.3 ##STR246## O O H CH350 ##STR247## COOCH.sub.3 ##STR248## O O H CH351 ##STR249## COOCH.sub.3 OH O O H CH352 ##STR250## COOCH.sub.3 ##STR251## O O H CH__________________________________________________________________________ TABLE 24__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________353 ##STR252## COOCH.sub.3 OCH.sub.2 OC.sub.2 H.sub.5 O O H CH354 CH.sub.3 COOCH.sub.2 SCH.sub.3 OCH.sub.2 CHCH.sub.2 O O H CH 99-101355 CH.sub.3 COOCH.sub.2 SCH.sub.3 OH O O H CH 152-155.5356 CH.sub.3 COOCH.sub.2 CF.sub.3 OH O O H CH 152.5-155357 CH.sub.3 COOCH.sub.2 CF.sub.3 OCH.sub.2 CHCH.sub.2 O O H CH 114-116358 CH.sub.3 COOCH.sub.2 CF.sub.3 ##STR253## O O H CH359 CH.sub.3 COOH ##STR254## O O H CH 222-225360 CH.sub.3 COC.sub.2 H.sub.5 ##STR255## O O H CH361 CH.sub.3 COC.sub.2 H.sub.5 OH O O H CH362 CH.sub.3 COC.sub.3 H.sub.7 ##STR256## O O H CH363 CH.sub.3 COC.sub.3 H.sub.7 OH O O H CH364 CH.sub.3 COC.sub.4 H.sub.9 ##STR257## O O H CH 119-121365 CH.sub.3 COC.sub.4 H.sub.9 OH O O H CH 136-138366 CH.sub.3 COC.sub.5 H.sub.11 ##STR258## O O H CH 106-109367 CH.sub.3 COC.sub.5 H.sub.11 OH O O H CH 130-132368 CH.sub.3 ##STR259## OH O O H CH Unmeasurable369 CH.sub.3 ##STR260## ##STR261## O O H CH 1.5519__________________________________________________________________________ TABLE 25__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Yn Z or (n.sub.D.sup.20)__________________________________________________________________________370 CH.sub.3 COOH ##STR262## O O H CH 132-135371 CH.sub.3 COOH OCH.sub.2 CHCH.sub.2 O O H CH 207-210372 H COOCH.sub.2 C.sub.4 H.sub.9 -t OH O O H CH373 H COSC.sub.2 H.sub.5 OH O O H CH374 H CONHC.sub.2 H.sub.5 OH O O H CH375 H CON(CH.sub.3).sub.2 OH O O H CH376 H COSC.sub.3 H.sub.7 OH O O H CH377 H COSC.sub.4 H.sub.9 OH O O H CH378 CH.sub.3 OCH.sub.2 COOCH.sub.3 ##STR263## O O H CH 92-95379 CH.sub.3 OCH.sub.2 COOCH.sub.3 OH O O H CH 150-153380 CH.sub.3 OCH.sub.2 COOC.sub.2 H.sub.5 ##STR264## O O H CH381 CH.sub.3 OC.sub.2 H.sub.4 COOCH.sub.3 ##STR265## O O H CH382 CH.sub.3 OC.sub.2 H.sub.4 COOCH.sub.3 OH O O H CH383 CH.sub.3 OC.sub.2 H.sub.4 COOCH.sub.3 ##STR266## O O H CH__________________________________________________________________________ TABLE 26__________________________________________________________________________ ##STR267##Compound m.p. (.degree.C.)No. R.sup.2 R.sup.3 R.sup.4 R W Z or (n.sub.D.sup.20)__________________________________________________________________________384 COOCH.sub.3 CH.sub.3 CH.sub.3 ##STR268## O CH 145-147385 COOCH.sub.3 CH.sub.3 CH.sub.3 OH O CH 174-177386 COOCH.sub.3 CH.sub.3 OCH.sub.3 OH O CH 138-140387 COOCH.sub.3 CH.sub.3 Cl OH O CH388 COOCH.sub.3 CH.sub.3 OCH.sub.3 ##STR269## O CH 102.5-106389 COOCH.sub.3 CH.sub.3 OCH.sub.3 OH O N 143-146390 COOCH.sub.3 CH.sub.3 OCH.sub.3 ##STR270## O N 117-120391 COOCH.sub.3 OCH.sub.3 Cl OH O CH 162-164392 COOCH.sub.3 OCH.sub.3 NHCH.sub.3 OH O CH393 COOCH.sub.3 OCH.sub.3 OCHF.sub.2 OH O CH 151-155394 COOCH.sub.3 OCHF.sub.2 OCHF.sub.2 OH O CH395 COOCH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 OH O CH 167-170396 COOCH.sub.3 CH.sub.3 CH.sub.3 ##STR271## O N397 COOCH.sub.3 CH.sub.3 OCH.sub.3 ##STR272## O CH398 COOCH.sub.3 Cl OCH.sub.3 ##STR273## O CH 129-132__________________________________________________________________________ TABLE 27__________________________________________________________________________ ##STR274##Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Z or (n.sub.D.sup.20)__________________________________________________________________________399 H H H O S CH400 H H OH O S CH401 H H ##STR275## O S CH402 H H H O NCH.sub.3 CH403 H H OH O NCH.sub.3 CH404 H H ##STR276## O NCH.sub.3 CH405 H COOC.sub.2 H.sub.5 H O O CH 116-124406 H COOC.sub.2 H.sub.5 OH O O CH407 H COOC.sub.2 H.sub.5 ##STR277## O O CH408 CH COOC.sub.2 H.sub.5 H O O CH409 CH.sub.3 COOC.sub.2 H.sub.5 OH O O CH410 H COOC.sub.2 H.sub.5 OH O NCH.sub.3 CH411 H COOC.sub.2 H.sub.5 OH O S CH412 COOC.sub.2 H.sub.5 H H O O CH413 COOC.sub.2 H.sub.5 H OH O O CH414 COOC.sub.2 H.sub.5 H H O NCH.sub.3 CH415 COOC.sub.2 H.sub.5 H H O NCH.sub.3 N416 COOC.sub.2 H.sub.5 CH.sub.3 OH O O CH417 COOC.sub.2 H.sub.5 H OH O NCH.sub.3 CH418 COOC.sub.2 H.sub.5 H H O S CH419 COOC.sub.2 H.sub.5 H OH O S CH420 COOC.sub.2 H.sub.5 H H O S CH421 COOC.sub.2 H.sub.5 H OH O S CH422 H CH.sub.3 ##STR278## O NCH.sub.3 CH__________________________________________________________________________ TABLE 28__________________________________________________________________________Compound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W X Z or (n.sub.D.sup.20)__________________________________________________________________________423 H CH.sub.3 OH O NCH.sub.3 CH424 H H OCH.sub.2 OCH.sub.3 O NCH.sub.2 CHCH.sub.2 CH425 H H OH O NCH.sub.2 CHCH.sub.2 CH426 H CH.sub.3 OCH.sub.2 OCH.sub.3 O NCH.sub.2 CHCH.sub.2 CH427 H CH.sub.3 OH O NCH.sub.2 CHCH.sub.2 CH428 H CH.sub.3 OCH.sub.2 CHCH.sub.2 O NCH.sub.2 COOCH.sub.3 CH429 H CH.sub.3 OH O NCH.sub.2 COOCH.sub.3 CH430 H CH.sub.3 ##STR279## O NC(O)CH.sub.3 CH431 H CH.sub.3 OH O NC(O)CH.sub.3 CH432 H CH.sub.3 ##STR280## O ##STR281## CH433 H CH.sub.3 OH O ##STR282## CH434 H CH.sub.3 ##STR283## O NCOOC.sub.2 H.sub.5 CH435 H CH.sub.3 OH O NCOOC.sub.2 H.sub.5 CH436 H CH.sub.3 ##STR284## O ##STR285## CH437 H CH.sub.3 OH O ##STR286## CH438 H CH.sub.3 ##STR287## O ##STR288## CH439 H CH.sub.3 OH O ##STR289## CH440 H CH.sub.3 OCH.sub.2 CHCH.sub.2 O NSO.sub.2 CH.sub.3 CH441 H CH.sub.3 OH O NSO.sub.2 CH.sub.3 CH442 H CH.sub.3 ##STR290## O NH CH443 H CH.sub.3 OH O NH CH444 H CH.sub.3 OH O NH N__________________________________________________________________________ TABLE 29__________________________________________________________________________ ##STR291##Compound m.p. (.degree.C.)No. R.sup.1 R W X Z or (n.sub.D.sup.20)__________________________________________________________________________445 H ##STR292## O O CH Unmeasurable446 H OCH.sub.3 O O CH 144-148447 H OH O O CH448 H OH O O N449 H OH S O CH450 H OH S O N451 CH.sub.3 OH O O CH452 C.sub.2 H.sub.5 OH O O CH453 ##STR293## OH O O CH454 H OH O NH CH455 CH.sub.3 OH O NH CH456 H OH O NH N457 H OH O S CH458 CH.sub.3 OH O S CH459 H OH O S N460 CH.sub.3 OH O S N__________________________________________________________________________ TABLE 30__________________________________________________________________________ ##STR294##Compound m.p. (.degree.C.)No. R.sup.1 R.sup.3 R.sup.4 R W X Z or (n.sub.D.sup.20)__________________________________________________________________________461 H OCH.sub.3 OCH.sub.3 OC.sub.2 H.sub.5 O O CH 111-114462 H OCH.sub.3 OCH.sub.3 OCH.sub.3 O O CH 125-127463 H OCH.sub.3 OCH.sub.3 OH O O CH 168-174464 H OCH.sub.3 OCH.sub.3 OCH.sub.3 O O N 141-144465 H OCH.sub.3 OCH.sub.3 OH O O N466 H OCH.sub.3 OCH.sub.3 OH S O CH467 H OCH.sub.3 OCH.sub.3 OH S O N468 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O O CH 162-165469 CH.sub.3 OCH.sub.3 OCH.sub.3 OH O O CH 204-210470 CH.sub.3 OCH.sub.3 OCH.sub.3 OH O O N471 CH.sub.3 OCH.sub.3 OCH.sub.3 OH S O CH472 H OCH.sub.3 OCH.sub.3 OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 O O CH 1.5343473 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.2 OC.sub.2 H.sub.5 O O N474 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 OH O O CH475 ##STR295## OCH.sub.3 OCH.sub.3 OH O O CH 210-211476 H CH.sub.3 CH.sub.3 OCH.sub.3 O O CH 1.5582477 H OCH.sub.3 OCH.sub.3 OCH.sub.2 OC.sub.2 H.sub.5 O O CH Unmeasurable478 H OCH.sub.3 OCH.sub.3 OH O S CH479 CH.sub.3 OCH.sub.3 OCH.sub.3 OH O S CH480 H OCH.sub.3 OCH.sub.3 OH O S N481 CH.sub.3 OCH.sub.3 OCH.sub.3 OH O S N482 CH.sub.2 NO.sub.2 OCH.sub.3 OCH.sub.3 OH O S CH 168-169483 CH.sub.3 OCH.sub.3 OCH.sub.3 OH ##STR296## O CH__________________________________________________________________________ TABLE 31______________________________________ ##STR297##Com-pound m.p. (.degree.C.)No. R.sup.1 R W X Z or (n.sub.D.sup.20)______________________________________484 H OH O O CH485 H OH S O CH486 H OH O O N487 CH.sub.3 OCH.sub.3 O O CH 167-171488 CH.sub.3 OH O O CH 155-159489 CH.sub.3 OH O O N490 CH.sub.3 OH S O N491 CH.sub.3 OH S O CH492 H OH O S CH493 H OH O S N494 H OH O NH CH495 H OH O NCH.sub.3 CH______________________________________ TABLE 32______________________________________ ##STR298## m.p.Com- (.degree.C.)pound orNo. R.sup.1 R.sup.3 R.sup.4 R W X Z (n.sub.D.sup.20)______________________________________496 H OCH.sub.3 OCH.sub.3 OH O O CH497 H OCH.sub.3 OCH.sub.3 OH S O CH498 H OCH.sub.3 OCH.sub.3 OH O NH CH 169- 171499 CH.sub.3 OCH.sub.3 OCH.sub.3 OH O O CH500 CH.sub.3 OCH.sub.3 OCH.sub.3 OH O O N501 CH.sub.3 OCH.sub.3 OCH.sub.3 OH S O N502 CH.sub.3 CH.sub.3 CH.sub.3 OH O O CH503 CH.sub.3 CH.sub.3 OCH.sub.3 OH O O CH504 H OCH.sub.3 OCH.sub.3 OH O S CH505 H OCH.sub.3 OCH.sub.3 OH O S N506 H OCH.sub.3 OCH.sub.3 OH O NCOCH.sub.3 CH 175- 178______________________________________ TABLE 33______________________________________ ##STR299##Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R W Z or (n.sub.D.sup.20)______________________________________507 OC.sub.2 H.sub.5 H OCH.sub.3 O CH 1.5243508 OC.sub.2 H.sub.5 H OH O CH 1.5306509 CH.sub.3 H OCH.sub.3 O CH 1.5319510 CH.sub.3 H OH O CH Un- measurable511 CH.sub.3 H OCH.sub.3 O N512 CH.sub.3 H OH O N513 CH.sub.3 H OCH.sub.3 S CH514 CH.sub.3 H OH S CH515 OC.sub.2 H.sub.5 H OCH.sub.3 O N516 OC.sub.2 H.sub.5 H OH O N517 OC.sub.2 H.sub.5 H OH S CH518 OC.sub.2 H.sub.5 H OH S N519 OC.sub.2 H.sub.5 CH.sub.3 ##STR300## O CH 1.5575520 OC.sub.2 H.sub.5 CH.sub.3 OH O CH 105-109521 OC.sub.2 H.sub.5 CH.sub.3 ##STR301## O CH522 OC.sub.2 H.sub.5 CN ##STR302## O CH523 OC.sub.2 H.sub.5 CN OH O CH524 OC.sub.2 H.sub.5 CN ##STR303## O CH525 OC.sub.2 H.sub.5 COCH.sub.3 ##STR304## O CH526 OC.sub.2 H.sub.5 COCH.sub.3 OH O CH527 OC.sub.2 H.sub.5 COCH.sub.3 ##STR305## O CH______________________________________ TABLE 34__________________________________________________________________________ ##STR306##Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________528 CH.sub.3 COOC.sub.2 H.sub.4 SCH.sub.3 OCH.sub.2 OCOC.sub.4 H.sub.9 -t O 69-71529 CH.sub.3 COOH OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 139-141530 CH.sub.3 COOCH.sub.2 CHCHCH.sub.3 OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 1.5441531 CH.sub.3 COOCH.sub.2 CHCHCl OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O Unmeasurable532 CH.sub.3 COOCH.sub.2 CClCHCl OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 1.5488533 CH.sub.3 COOCH.sub.2 CHCHCH.sub.3 OH O 143-144534 CH.sub.3 COOCH.sub.2 CHCHCl OH O 146-148535 CH.sub.3 COOCH.sub.2 CClCHCl OH O 155-158536 CH.sub.3 ##STR307## OCH.sub.2 CHCH.sub.2 O 191-194537 CH.sub.3 ##STR308## OCH.sub.2 CHCH.sub.2 O 128-131538 CH.sub.3 CONHC.sub.3 H.sub.7 -i OCH.sub.2 OCOC.sub.4 H.sub.9 -t O 183-184.5539 CH.sub.3 COSC.sub.5 H.sub.11 OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t O 1.5380540 CH.sub.3 COONC(CH.sub.3).sub.2 OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t O 186-189541 H COOCH.sub.2 CHCH.sub.2 ##STR309## O 85-87542 H COOH ##STR310## O 174-175543 CH.sub.3 ##STR311## OCH.sub.2 CHCH.sub.2 O 114-116544 CH.sub.3 CONHC.sub.4 H.sub.9 OCH.sub.2 CHCH.sub.2 O 148-150545 CH.sub.3 COOCH.sub.2 C(CH.sub.3)CH.sub.2 OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 1.5438546 CH.sub.3 COOCH(CH.sub.3)CHCH.sub.2 OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 1.5373547 CH.sub.3 COOCH.sub.2 CHC(CH.sub.3).sub.2 OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 1.5461548 CH.sub.3 COOCH.sub.2 C CCH.sub.3 OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 69-71549 CH.sub.3 COOCH.sub.2 CH.sub.2 C CH OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 66-68550 CH.sub.3 COOCH(CH.sub.3)C CH OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 1.5420551 CH.sub.3 COOCH(CH.sub.3)CHCH.sub.2 OH O 140-144.5__________________________________________________________________________ TABLE 35__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________552 CH.sub.3 COOCH.sub.2 C CCH.sub.3 OH O 174-178553 CH.sub.3 COOCH.sub.2 CH.sub.2 C CH OH O Unmeasurable554 CH.sub.3 COOCH(CH.sub.3)C CH OH O 160-165555 CH.sub.3 COSCH(CH.sub.3)C.sub.2 H.sub.5 OCH.sub.2 CHCH.sub.2 O 100-103556 CH.sub.3 COOC.sub.3 H.sub.7 OCH(CH.sub.3)OCOC.sub.4 H.sub.9 O 102-106557 CH.sub.3 COOC.sub.3 H.sub.7 OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t O 126-129558 CH.sub.3 CONHC.sub.4 H.sub.9 OH O 177-179559 CH.sub.3 CON(CH.sub.3)C.sub.4 H.sub.9 OCH.sub.2 CHCH.sub.2 O 1.5465560 CH.sub.3 CON(CH.sub.3)C.sub.4 H.sub.9 OH O 162-166561 CH.sub.3 ##STR312## OCH.sub.2 CHCH.sub.2 O 218-220562 CH.sub.3 COSC.sub.4 H.sub.9 -i OH O 130-133563 CH.sub.3 ##STR313## OH O 158-163564 CH.sub.3 COOCH.sub.2 C CC.sub.2 H.sub.5 OCH.sub.2 OCH.sub.3 O 95-97565 CH.sub.3 COOCH.sub.2 CH.sub.2 C CCH.sub.3 OCH.sub.2 OCH.sub.3 O 140.5-143566 CH.sub.3 COOCH.sub.2 CH.sub.2 CH.sub.2 C CH OCH.sub.2 OCH.sub.3 O 78-81567 CH.sub.3 COOCH(CH.sub.3)CH.sub.2 C CH OCH.sub.2 OCH.sub.3 O 137-138.5568 CH.sub.3 COOCH(C.sub.2 H.sub.5)C CH OCH.sub.2 OCH.sub.3 O 138-140569 CH.sub.3 COSCH.sub.2 CHCH.sub.2 OCH.sub.2 OCH.sub.3 O 1.5850570 CH.sub.3 COOCH.sub.2 C CC.sub.2 H.sub.5 OH O 167-169571 CH.sub.3 COOCH.sub.2 CH.sub.2 C CCH.sub.3 OH O Unmeasurable572 CH.sub.3 COOCH.sub.2 CH.sub.2 CH.sub.2 C CH OH O 160-161.5573 CH.sub.3 COOCH(CH.sub.3)CH.sub.2 C CH OH O 133-135574 CH.sub.3 COOCH(C.sub.2 H.sub.5)C CH OH O 155-156.5575 C.sub.2 H.sub.5 COOH OH O 171-174.5576 CH.sub.3 COOC.sub.3 H.sub.7 OCH(CH.sub.3)OCOC.sub.2 H.sub.5 O 104.5-107577 CH.sub.3 COOC.sub.3 H.sub.7 OCH(CH.sub.3)OCOC.sub.3 H.sub.7 O 104-105.5578 CH.sub.3 COOC.sub.3 H.sub.7 OCH(CH.sub.3)OCOC.sub.3 H.sub.7 -i O 123-126579 CH.sub.3 COOC.sub.3 H.sub.7 OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -i O 124.5-126.5__________________________________________________________________________ TABLE 36__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________580 CH.sub.3 ##STR314## OCH.sub.2 CHCH.sub.2 O 97-99581 CH.sub.3 ##STR315## OH O 110-114582 CH.sub.3 COOCH.sub.2 CH.sub.2 Cl OCH.sub.2 CHCH.sub.2 O 99-101583 CH.sub.3 COOCH.sub.2 CHCl.sub.2 OCH.sub.2 CHCH.sub.2 O 97-98584 CH.sub.3 COOCH.sub.2 CCl.sub.3 OCH.sub.2 CHCH.sub.2 O 126-128.5585 CH.sub.3 COOCH.sub.2 CH.sub.2 Cl OH O 155-157586 CH.sub.3 COOCH.sub.2 CHCl.sub.2 OH O 129-132587 CH.sub.3 COOCH.sub.2 CCl.sub.3 OH O 97-101588 CH.sub.3 COOCH.sub.2 CH.sub.2 Br OCH.sub.2 CHCH.sub.2 O 106-108589 CH.sub.3 COOCH.sub.2 CH.sub.2 CN OCH.sub.2 CHCH.sub.2 O 128-130590 CH.sub.3 COOCH.sub.2 CH.sub.2 Br OH O 159-162591 CH.sub.3 COOCH.sub.2 CH.sub.2 CN OH O 177-179.5592 CH.sub.3 COOCH(CF.sub.3).sub.2 OCH.sub.2 CHCH.sub.2 O 139-141593 CH.sub.3 ##STR316## OCH.sub.2 CHCH.sub.2 O 85-89594 CH.sub.3 ##STR317## OCH.sub.2 CHCH.sub.2 O 98-101.5595 CH.sub.3 ##STR318## OH O 160-162596 CH.sub.3 ##STR319## OH O 155-158597 CH.sub.3 COSCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 OCH.sub.2 CHCH.sub.2 O 72-74598 CH.sub.3 COSCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2 OH O 99-101599 CH.sub.3 COSCH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2 OCH.sub.2 CHCH.sub.2 O 68-69.5600 CH.sub.3 COSCH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2 OH O 139-142601 H COOCH.sub.2 OH O 158-163602 C.sub.2 H.sub.5 ##STR320## ##STR321## O 110-112__________________________________________________________________________ TABLE 37__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________603 C.sub.2 H.sub.5 COC.sub.2 H.sub.5 OH O 140.5-143604 C.sub.4 H.sub.9 COCH.sub.3 OH O 134-136605 H ##STR322## OCH.sub.2 CHCH.sub.2 O 100-103606 CH.sub.3 H OCH.sub.2 CHCH.sub.2 S 89-91607 CH.sub.3 H OH S 151-155608 CH.sub.3 COOC.sub.2 H.sub.5 ##STR323## NCH.sub.3 151-156609 CH.sub.3 COOC.sub.2 H.sub.5 OH NCH.sub.3 200-202610 CH.sub.3 COOC.sub.4 H.sub.9 -t ##STR324## NH 183-187611 CH.sub.3 COOC.sub.4 H.sub.9 -t OH NH 187-190612 CH.sub.3 H OH NH 167-170613 CH.sub.3 COOCH.sub.3 ##STR325## NH 164-166614 CH.sub.3 COOCH.sub.3 OH NH 194-197615 CH.sub.3 COOCH.sub.2 CHCH.sub.2 ##STR326## NH 204-208616 CH.sub.3 COOH ##STR327## NH 161-164617 CH.sub.3 COOC.sub.3 H.sub.7 OH NH 175-179618 CH.sub.3 COOC.sub.3 H.sub.7 -i OH NH 180-183619 CH.sub.3 COOC.sub.4 H.sub.9 OH NH 143-148620 CH.sub.3 COOC.sub.4 H.sub.9 -i OH NH 140-146.5621 CH.sub.3 COOC.sub.4 H.sub.9 -s OH NH 145-150622 CH.sub.3 COOC.sub.5 H.sub.11 OH NH 119-123623 CH.sub.3 COOC.sub.6 H.sub.13 OH NH 125-130624 CH.sub.3 COOC.sub.3 H.sub.7 ##STR328## NH 207-209__________________________________________________________________________ TABLE 38__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________625 CH.sub.3 COOC.sub.3 H.sub.7 -i ##STR329## NH 203-205626 CH.sub.3 COOC.sub.4 H.sub.9 ##STR330## NH 191.5-194627 CH.sub.3 COOC.sub.4 H.sub.9 -i ##STR331## NH 200-203628 CH.sub.3 COOC.sub.4 H.sub.9 -s ##STR332## NH 170-173629 CH.sub.3 COOC.sub.5 H.sub.11 ##STR333## NH 137-139630 CH.sub.3 COOC.sub.6 H.sub.13 ##STR334## NH 130-133631 CH.sub.3 ##STR335## ##STR336## NH 181-184632 CH.sub.3 ##STR337## ##STR338## NH 192.5-196633 CH.sub.3 COOCH.sub.2 CH.sub.2 OCH.sub.3 ##STR339## NH 187-190634 CH.sub.3 COCF.sub.3 OH NH 162-167635 CH.sub.3 COCF.sub.3 ##STR340## NH 165-167636 CH.sub.3 ##STR341## OH NH 223-227637 CH.sub.3 COOCH.sub.2 CH.sub.2 OCH.sub.3 OH NH 182-186638 CH.sub.3 Cl OH NH 176-179639 CH.sub.3 COC.sub.2 H.sub.5 OH NH 192-195640 CH.sub.3 COC.sub.2 H.sub.5 ##STR342## NH 173-176641 CH.sub.3 CN ##STR343## NH 151-154__________________________________________________________________________ TABLE 39__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________642 CH.sub.3 COCH.sub.3 OH NH 198-203643 CH.sub.3 COCH.sub.3 ##STR344## NH 206-211644 CH.sub.3 CN ##STR345## O 156-158645 CH.sub.3 Br OH S 178-180646 CH.sub.3 Br OCH.sub.2 C(Br)CH.sub.2 S 126-128647 CH.sub.3 Br OCH.sub.2 CHCH.sub.2 S648 CH.sub.3 COC.sub.3 H.sub.7 ##STR346## NH649 CH.sub.3 COC.sub.3 H.sub.7 OH NH 193-196650 CH.sub.3 CH.sub.2 CHCH.sub.2 OH NH 130-134651 CH.sub.3 C.sub.3 H.sub.7 OH NH 137-142652 CH.sub.3 COOCH.sub.2 CH.sub.2 F OH NH 193-195653 CH.sub.3 COOCH.sub.2 CH.sub.2 Cl OH NH 203-205654 CH.sub.3 COOCH(CH.sub.3)CH.sub.2 Cl OH O 143-147655 CH.sub.3 COOCH(CH.sub.2 Cl).sub.2 OH O 115-119656 CH.sub.3 COOCH(CH.sub.3)CH2F OH O 150-153657 CH.sub.3 COOCH(CH.sub.3)CF.sub.3 OH O 125-128658 CH.sub.3 COOCH.sub.2 CHF.sub.2 OH O 144-147659 CH.sub.3 COOCH.sub.2 CH.sub.2 CH.sub.2 F OH O 153-156660 CH.sub.3 COOCH.sub.2 CH.sub.2 OH OH O 148-151661 CH.sub.3 COOCH.sub.2 COOC.sub.2 H.sub.5 OH O 130-133662 CH.sub.3 ##STR347## OH O 154-157663 CH.sub.3 CON(C.sub.2 H.sub.5).sub.2 OH NH 151-155__________________________________________________________________________ TABLE 40__________________________________________________________________________ ##STR348##Com-pound m.p. (.degree.C.)No. R.sup.2 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________664 H ##STR349## NH O CH 135-139665 H OH NH O CH 167-170666 CH.sub.2 CHCH.sub.2 OCH.sub.3 NH O CH667 CH.sub.2 CHCH.sub.2 OH NH O CH 130-134668 CH.sub.2 C CH OCH3 NH O CH669 CH.sub.2 C CH OH NH O CH670 CH.sub.2 CN OCH3 NH O CH671 CH.sub.2 CN OH NH O CH 165-169672 CH.sub.2 COOCH.sub.3 ##STR350## NH O CH673 CH.sub.2 COOCH.sub.3 OH NH O CH674 CH.sub.2 N(CH.sub.3).sub.2 OCH.sub.2 CHCH.sub.2 NH O CH675 CH.sub.2 N(CH.sub.3).sub.2 OH NH O CH676 CHCHCN OCH.sub.2 CHCH.sub.2 NH O CH677 CHCHCN OH NH O CH678 CHCHNO.sub.2 OCH.sub.2 CHCH.sub.2 NH O CH679 CHCHNO.sub.2 OH NH O CH680 CHO ##STR351## NH O CH 148-149681 CHO OH NH O CH 201-206682 CHNC.sub.3 H.sub.7 -i OCH.sub.2 CHCH.sub.2 NH O CH683 CHNC.sub.3 H.sub.7 -i OH NH O CH684 ##STR352## OCH.sub.2 CHCH.sub.2 NH O CH__________________________________________________________________________ TABLE 41__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.2 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________685 ##STR353## OH NH O CH686 ##STR354## ##STR355## NH O CH687 ##STR356## OH NH O CH688 CHNN(CH.sub.3).sub.2 ##STR357## NH O CH689 CHNN(CH.sub.3).sub.2 OH NH O CH690 CHNOH ##STR358## NH O CH691 CHNOH OH NH O CH 165-170692 CHNOCH.sub.3 ##STR359## NH O CH 131-133693 CHNOCH.sub.3 OH NH O CH 171-175694 H OH NH O N 152-154695 CHNOCH.sub.3 OH NH O N696 CHNOCH.sub.3 OCH.sub.3 NH S CH697 CHNOCH.sub.3 OH NH S CH698 CHNOCH.sub.3 OCH.sub.2 C CH NH O CH699 CHNOCH.sub.3 OCH.sub.2 OCH.sub.3 NH O CH700 CHNOCH.sub.3 OCH(CH.sub.3)OC(O)C.sub.4 H.sub.9 -t NH O CH701 CHNOCH.sub.3 ##STR360## NH O CH702 CHNOCH.sub.3 ONC(CH.sub.3).sub.2 NH O CH703 CHNOCH.sub.3 SCH.sub.3 NH O CH704 CHNOCH.sub.3 SCH.sub.2 CHCH.sub.2 NH O CH705 CHNOCH.sub.3 SCH.sub.2 C CH NH O CH__________________________________________________________________________ TABLE 42__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.1 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________706 CHNOCH.sub.3 ##STR361## NH O CH707 CHNOCH.sub.3 NHC.sub.2 H.sub.5 NH O CH708 CHNOCH.sub.3 ##STR362## NH O CH709 CHNOCH.sub.3 NHSO.sub.2 CH.sub.3 NH O CH710 CHNOCH.sub.3 ##STR363## NH O CH711 CHNOCH.sub.3 ##STR364## NH O CH712 CHNOCH.sub.3 ##STR365## NH O CH713 CHNOC.sub.3 H.sub.7 -i ##STR366## NH O CH714 CHNOC.sub.3 H.sub.7 -i OH NH O CH 123-127715 CHNOCH.sub.2 CHCH.sub.2 OH NH O CH716 CHNOCH.sub.2 C CH OH NH O CH717 ##STR367## OCH.sub.2 CHCH.sub.2 NH O CH718 ##STR368## OH NH O CH719 ##STR369## OCH.sub.3 NH O CH720 ##STR370## OH NH O CH721 COOC.sub.2 H.sub.5 ##STR371## NH O CH 196-199722 NH.sub.2 OCH.sub.2 CHCH.sub.2 NH O CH 132-135__________________________________________________________________________ TABLE 43__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.2 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________723 NH.sub.2 ##STR372## NH O CH724 NH.sub.2 OH NH O CH725 NHCH.sub.3 ##STR373## NH O CH726 NHCH.sub.3 OH NH O CH727 ##STR374## OCH.sub.2 CHCH.sub.2 NH O CH728 ##STR375## OH NH O CH729 ##STR376## OCH.sub.2 CHCH.sub.2 NH O CH730 ##STR377## OH NH O CH731 N(CH.sub.3).sub.2 ##STR378## NH O CH732 N(CH.sub.3).sub.2 OH NH O CH733 ##STR379## ##STR380## NH O CH734 ##STR381## OH NH O CH735 NHC(O)CH.sub.3 OCH.sub.2 CHCH.sub.2 NH O CH 177-180736 NHC(O)CH.sub.3 OH NH O CH 230-233737 ##STR382## OCH.sub.2 CHCH.sub.2 NH O CH738 ##STR383## OH NH O CH 168-172739 NHCOOC.sub.2 H.sub.5 OCH.sub.2 CHCH.sub.2 NH O CH740 NHCOOC.sub.2 H.sub.5 OH NH O CH 177-179__________________________________________________________________________ TABLE 44__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.2 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________741 NHC(O)SC.sub.2 H.sub.5 OCH.sub.2 CHCH.sub.2 NH O CH742 NHC(O)SC.sub.2 H.sub.5 OH NH O CH743 ##STR384## OCH.sub.2 CHCH.sub.2 NH O CH744 ##STR385## OH NH O CH745 NHC(O)NHCH.sub.3 OCH.sub.2 CHCH.sub.2 NH O CH746 NHC(O)NHCH.sub.3 OH NH O CH747 NHC(O)N(CH.sub.3).sub.2 ##STR386## NH O CH748 NHC(O)N(CH.sub.3).sub.2 OH NH O CH749 NHSO.sub.2 CH.sub.3 OCH.sub.2 CHCH.sub.2 NH O CH750 NHSO.sub.2 CH.sub.3 OH NH O CH751 ##STR387## OCH.sub.2 CHCH.sub.2 NH O CH752 ##STR388## OH NH O CH753 NCHCH.sub.3 OCH.sub.2 CHCH.sub.2 NH O CH754 NCHCH.sub.3 OH NH O CH755 ##STR389## OCH.sub.2 CHCH.sub.2 NH O CH756 ##STR390## OH NH O CH 265-270757 ##STR391## OCH.sub.2 CHCH.sub.2 NH O CH758 ##STR392## OH NH O CH759 NO.sub.2 OCH.sub.2 CHCH.sub.2 NH O CH 155-159760 NO.sub.2 OH NH O CH >300.degree. C.__________________________________________________________________________ TABLE 45__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.2 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________761 NO.sub.2 OCH.sub.2 CHCH.sub.2 NCH.sub.3 O CH762 NO.sub.2 OH NCH.sub.3 O CH763 COOC.sub.2 H.sub.5 ##STR393## NCH.sub.2 CHCH.sub.2 O CH 1.5774764 COOC.sub.2 H.sub.5 OH NCH.sub.2 CHCH.sub.2 O CH765 NH.sub.2 ##STR394## NCH.sub.2 CHCH.sub.2 O CH766 NH.sub.2 OH NCH.sub.2 CHCH.sub.2 O CH 215-220767 H OCH.sub.2 OCH.sub.3 NCH.sub.2 C CH O CH768 H OH NCH.sub.2 C CH O CH769 COOC.sub.2 H.sub.5 OCH.sub.3 NCH.sub.2 OCH.sub.3 O CH770 COOC.sub.2 H.sub.5 OH NCH.sub.2 OCH.sub.3 O CH 158-162771 COOC.sub.2 H.sub.5 ##STR395## NCH.sub.2 OC(O)C.sub.4 H.sub.9 -t O CH 182-183.5772 COOC.sub.2 H.sub.5 OH NCH.sub.2 OC(O)C.sub.4 H.sub.9 -t O CH 193-195773 COOC.sub.2 H.sub.5 ##STR396## NCH.sub.2 COOC.sub.2 H.sub.5 O CH 141-143.5774 COOC.sub.2 H.sub.5 OH NCH.sub.2 COOC.sub.2 H.sub.5 O CH 190-193775 H OH NC(O)CH.sub.3 O CH776 H OH NC(O)CH.sub.3 CH.sub.2 CH777 H OH NC(O)CH.sub.3 CH(CN) CH778 H OH NC(O)CH.sub.3 C(O) CH779 H OCH.sub.3 NC(O)CH.sub.3 N(CHO) CH780 Cl OCH.sub.2 OCH.sub.3 NC(O)CH.sub.3 O CH781 Cl OH NC(O)CH.sub.3 O CH782 OCH.sub.3 ##STR397## NC(O)CH.sub.3 O CH__________________________________________________________________________ TABLE 46__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.2 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________783 OCH.sub.3 OH NC(O)CH.sub.3 O CH784 ##STR398## OCH.sub.2 CHCH.sub.2 NC(O)CH.sub.3 O CH785 ##STR399## OH NC(O)CH.sub.3 O CH786 COOCH.sub.3 ##STR400## NC(O)CH.sub.3 O CH 133-135787 COOCH.sub.3 OH NC(O)CH.sub.3 O CH 186-189788 COOC.sub.2 H.sub.5 ##STR401## NC(O)CH.sub.3 O CH 128-130.5789 COOC.sub.2 H.sub.5 OH NC(O)CH.sub.3 O CH 174-177790 COOCH.sub.2 CHCH.sub.2 OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 NC(O)CH.sub.3 O CH791 COOCH.sub.2 CHCH.sub.2 OH NC(O)CH.sub.3 O CH792 COOCH.sub.2 C CH OCH.sub.2 OCH.sub.3 NC(O)CH.sub.3 O CH793 COOCH.sub.2 C CH OH NC(O)CH.sub.3 O CH794 C(O)SCH.sub.3 OCH.sub.3 NC(O)CH.sub.3 O CH795 C(O)SCH.sub.3 OH NC(O)CH.sub.3 O CH796 COOC.sub.2 H.sub.5 ##STR402## ##STR403## O CH 128-132.5797 COOC.sub.2 H.sub.5 OH ##STR404## O CH 113-115798 ##STR405## OCH.sub.2 OCH.sub.3 ##STR406## O CH799 ##STR407## OH ##STR408## O CH__________________________________________________________________________ TABLE 47__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.2 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________800 ##STR409## ##STR410## ##STR411## O CH801 ##STR412## OH ##STR413## O CH802 C(O)SCH.sub.2 CHCH.sub.2 OCH.sub.2 CHCH.sub.2 ##STR414## O CH803 C(O)SCH.sub.2 CHCH.sub.2 OH ##STR415## O CH804 C(O)SCH.sub.2 C CH OCH.sub.2 CHCH.sub.2 ##STR416## O CH805 C(O)SCH.sub.2 C CH OH ##STR417## O CH806 C(O)CH.sub.3 ##STR418## ##STR419## O CH807 C(O)CH.sub.3 OH ##STR420## O CH808 ##STR421## OH ##STR422## O CH809 ##STR423## OH ##STR424## O CH810 ##STR425## OH ##STR426## O CH811 H OH ##STR427## O CH812 COOC.sub.2 H.sub.5 ##STR428## NCOOC.sub.2 H.sub.5 O CH 105-108813 COOC.sub.2 H.sub.5 OH NCOOC.sub.2 H.sub.5 O CH 170-173814 COOC.sub.2 H.sub.5 ##STR429## NCOOC.sub.4 H.sub.9 -t O CH 1.5649815 COOC.sub.2 H.sub.5 OH NCOOC.sub.4 H.sub.9 -t O CH 138-142__________________________________________________________________________ TABLE 48__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.2 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________816 H OCH.sub.2 CHCH.sub.2 ##STR430## O CH817 H OH ##STR431## O CH818 H ##STR432## ##STR433## O CH819 H OH ##STR434## O CH820 H OCH.sub.2 CHCH.sub.2 NC(O)SCH.sub.3 O CH821 H OH NC(O)SCH.sub.3 O CH822 H OCH.sub.2 CHCH.sub.2 ##STR435## O CH823 H OH ##STR436## O CH824 COOC.sub.2 H.sub.5 ##STR437## NC(O)N(CH.sub.3).sub.2 O CH 1.5767825 COOC.sub.2 H.sub.5 OH NC(O)N(CH.sub.3).sub.2 O CH 172-174826 COOC.sub.2 H.sub.5 ##STR438## NSO.sub.2 CH.sub.3 O CH 140.5-145827 COOC.sub.2 H.sub.5 OH NSO.sub.2 CH.sub.3 O CH 186-188828 COOC.sub.2 H.sub.5 ##STR439## ##STR440## O CH Unmeasurable829 COOC.sub.2 H.sub.5 OH ##STR441## O CH 149-152830 COOC.sub.2 H.sub.5 ##STR442## NSi(CH.sub.3).sub.2 C.sub.4 H.sub.9 -t O CH Unmeasurable831 COOC.sub.2 H.sub.5 OH NSi(CH.sub.3).sub.2 C.sub.4 H.sub.9 -t O CH 175-178832 COOC.sub.2 H.sub.5 ##STR443## NSCCl.sub.3 O CH 173-177__________________________________________________________________________ TABLE 49__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.2 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________833 COOC.sub.2 H.sub.5 OH NSCCl.sub.3 O CH834 H OCH.sub.3 ##STR444## O CH 187-190835 H OH ##STR445## O CH 182-183.5836 CN ##STR446## ##STR447## O CH 176-177837 H ##STR448## NC(O)CH.sub.3 O CH838 H OH NC(O)CH.sub.3 O CH839 H OCH.sub.2 CHCH.sub.2 NC(O)CH.sub.3 O CH840 H OH NC(O)CH.sub.3 O CH841 H OH NC(O)CH.sub.3 O CH__________________________________________________________________________ TABLE 50__________________________________________________________________________ ##STR449##Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R X W Z or (n.sub.D.sup.20)__________________________________________________________________________842 CH.sub.3 H CH.sub.3 CH.sub.3 OH NH O CH 184-186843 CH.sub.3 CHNOCH.sub.3 CH.sub.3 CH.sub.3 OH NH O CH844 CH.sub.3 H N(CH.sub.3).sub.2 OCH.sub.3 OH NH O CH 164-167845 CH.sub.3 H NHCH.sub.3 OCH.sub.3 OH NC(O)CH.sub.3 O CH846 CF.sub.3 H OCH.sub.3 OCH.sub.3 OH NC(O)CH.sub.3 O CH__________________________________________________________________________ TABLE 51__________________________________________________________________________ ##STR450##Com-pound m.p. (.degree.C.)No. X.sup.1 Q.sup.1 X.sup.2 R or (n.sub.D.sup.20)__________________________________________________________________________847 CH.sub.2 CH.sub.2 CO OCH.sub.3 150-153848 CH.sub.2 CH.sub.2 CO OH 181.5-184849 CH.sub.2 CH.sub.2 CNOCH.sub.3 OCH.sub.3 152-154850 CH.sub.2 CH.sub.2 CNOCH.sub.3 OH851 CH.sub.2 CH.sub.2 CHOH OCH.sub.3 135-137852 CH.sub.2 CH.sub.2 CHOH OH 151-153.5853 NH CO O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 Unmeasurable854 NH CO O OH 188-189855 NH CO NH OCH.sub.3856 NH CO NH OH857 NH CC(CN)COOCH.sub.3 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 100-105858 NH CC(CN)COOCH.sub.3 O OH 250-260859 NH CC(CN).sub.2 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 185-187860 NH CC(CN).sub.2 O O.sup.- N.sup.+ (C.sub.4 H.sub.9).sub.4 125-130861 NH ##STR451## O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3862 NH ##STR452## O OH863 NH ##STR453## O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3864 NH ##STR454## O OH865 O CO S OCH.sub.3 138-139866 O CO S OH__________________________________________________________________________ TABLE 52__________________________________________________________________________ ##STR455##Com-pound m.p. (.degree.C.)No. X.sup.1 Q.sup.2 Q.sup.3 X.sup.2 R or (n.sub.D.sup.20)__________________________________________________________________________867 CH.sub.2 CH.sub.2 CH.sub.2 CO OCH.sub.3 185-187868 CH.sub.2 CH.sub.2 CH.sub.2 CO OH 183-189869 CH.sub.2 CH.sub.2 CH.sub.2 CNOCH.sub.3 OCH.sub.3 128-131870 CH.sub.2 CH.sub.2 CH.sub.2 CNOCH.sub.3 OH871 CH.sub.2 CH.sub.2 CH.sub.2 CHOH OCH.sub.3872 CH.sub.2 CH.sub.2 CH.sub.2 CHOH OH 147.5-149873 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 ##STR456## 1.5332874 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 127-128875 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH 141-147876 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.2 O OCH.sub.3877 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.2 O OH 151-153878 NH CO CH.sub.2 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 148-150879 NH CO CH.sub.2 O OH 200-202880 NCH.sub.3 CO CH.sub.2 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 Unmeasurable881 NCH.sub.3 CO CH.sub.2 O OH 178-180882 NH CO CH(C.sub.2 H.sub.5) O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 Unmeasurable883 NH CO CH(C.sub.2 H.sub.5) O OH 195-197884 NH CH.sub.2 CH.sub.2 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 1.5333885 NH CH.sub.2 CH.sub.2 O OH 160-164886 NH CH.sub.2 CH.sub.2 S OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 Unmeasurable887 NH CH.sub.2 CH.sub.2 S OH 164-166888 NH CH.sub.2 CH.sub.2 NH OCH.sub.3889 NH CH.sub.2 CH.sub.2 NH OH890 NH CH(CH.sub.3) CH.sub.2 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 Unmeasurable891 NH CH(CH.sub.3) CH.sub.2 O OH 174-175892 NH CH.sub.2 CH(CH.sub.3) O OH 110-115893 NH CH.sub.2 CH(C.sub.2 H.sub.5) O OH__________________________________________________________________________ TABLE 53__________________________________________________________________________Com-pound m.p. (.degree.C.)No. X.sup.1 Q.sup.2 Q.sup.3 X.sup.2 R or (n.sub.D.sup.20)__________________________________________________________________________894 NH CH.sub.2 C(CH.sub.3).sub.2 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3895 NH CH.sub.2 C(CH.sub.3).sub.2 O OH896 NH CH.sub.2 CCH.sub.2 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 Unmeasurable897 NH CH.sub.2 CCH.sub.2 O OH 90-95898 NH CH.sub.2 CCHCH.sub.3 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3899 NH CH.sub.2 CCHCH.sub.3 O OH900 NH CH.sub.2 CH(CH.sub.2 COOCH.sub.3) O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3 Unmeasurable901 NH CH.sub.2 CH(CH.sub.2 COOCH.sub.3) O OH__________________________________________________________________________ TABLE 54______________________________________ ##STR457##Com-pound m.p. (.degree.C.)No. a b d e R or (n.sub.D.sup.20)______________________________________902 N CH CH CH H 159-161903 N CH CH CH OH 195-198904 N CH CH CH OCH.sub.3 160-162905 CH N CH CH H906 CH N CH CH OH907 CH N CH CH OCH.sub.3908 CH CH N CH H909 CH CH N CH OH910 CH CH N CH OCH.sub.3911 N N CH CH H912 N N CH CH OH913 N N CH CH OCH.sub.3914 N CH N CH H915 N CH N CH OH 174-177916 N CH N CH OCH.sub.3917 N CH CH N H918 N CH CH N OH 148-151919 N CH CH N OCH.sub.3 164-166920 CH N N CH H921 CH N N CH OH922 CH N N CH OCH.sub.3923 CH N CH N H924 CH N CH N OH925 CH N CH N OCH.sub.3926 CH CH N N H927 CH CH N N OH928 CH CH N N OCH.sub.3______________________________________ TABLE 55__________________________________________________________________________ ##STR458##Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________929 CH.sub.3 COOCH(CH.sub.2 F).sub.2 OH O 149-152930 CH.sub.3 COOH OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3 O 139-141931 CH.sub.3 COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5 OH O 143.5-146932 CH.sub.3 COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5 OCH.sub.2 CHCH.sub.2 O 92-94933 CH.sub.3 COOCH.sub.2 CH(OCH.sub.3).sub.2 OH O 153-155934 CH.sub.3 COOCH.sub.2 CH(OCH.sub.3).sub.2 OCH.sub.2 CHCH.sub.2 O 75-77935 CH.sub.3 COOCH.sub.2 C(CH.sub.3)CH.sub.2 OH O 143-146936 CH.sub.3 COOCH.sub.2 C(CH.sub.3)CH.sub.2 OCH.sub.2 OCH.sub.3 O 98-100937 CH.sub.3 COOC.sub.2 H.sub.4 N(CH.sub.3).sub.2 OH O 194-197938 CH.sub.3 COOCH.sub.2 CHC(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3 O 96-98939 CH.sub.3 COOCH(CH.sub.3)CHCHCH.sub.3 OCH.sub.2 OCH.sub.3 O 72-75940 CH.sub.3 COOCH(CH.sub.3)CH.sub.2 Cl OCH.sub.2 CHCH.sub.2 O 114-116941 CH.sub.3 COOCH(CH.sub.2 Cl).sub.2 OCH.sub.2 CHCH.sub.2 O 138-140942 CH.sub.3 COOCH(CH.sub.3)CH.sub.2 F OCH.sub.2 CHCH.sub.2 O 104-107943 CH.sub.3 COOCH(CH.sub.3)CF.sub.3 OCH.sub.2 CHCH.sub.2 O 118-119.5944 CH.sub.3 COOCH.sub.2 CHF.sub.2 OCH.sub.2 CHCH.sub.2 O 103-106945 CH.sub.3 COOCH.sub.2 CH.sub.2 CH.sub.2 F OCH.sub.2 CHCH.sub.2 O 58-61946 CH.sub.3 COOCH.sub.2 CH.sub.2 OH OCH.sub.2 CHCH.sub.2 O 121-124947 CH.sub.3 COOCH.sub.2 CO.sub.2 C.sub.2 H.sub.5 OCH.sub.2 CHCH.sub.2 O 93-95948 CH.sub.3 ##STR459## OCH.sub.2 CHCH.sub.2 O 109-110949 H H OH N-Pym 190-193950 H H OH NH 169-170951 CH.sub.3 CN ##STR460## NH 169-172__________________________________________________________________________ (In this Table, Pym indicates 4,6dimethoxypirimidin-2-yl.) TABLE 56__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________952 CH.sub.3 CN OH NH 185-189953 CH.sub.3 CH.sub.2 CN ##STR461## NH 151-156954 CH.sub.3 COCOOC.sub.2 H.sub.5 ##STR462## NH 150-153955 CH.sub.3 COCOOC.sub.2 H.sub.5 OH NH 179-183956 CH.sub.3 ##STR463## ##STR464## NH 82-85957 CH.sub.3 ##STR465## OH NH 143-146958 CH.sub.3 ##STR466## ##STR467## NH 89-92959 CH.sub.3 ##STR468## OH NH 127-129960 CH.sub.3 ##STR469## ##STR470## NH 94-99961 CH.sub.3 ##STR471## OH NH 137-140962 CH.sub.3 ##STR472## ##STR473## NH 103-105963 CH.sub.3 ##STR474## OH NH 170-173964 CH.sub.3 ##STR475## ##STR476## NH 106-109965 CH.sub.3 ##STR477## OH NH 123-125966 CH.sub.3 ##STR478## ##STR479## NH 89-91967 CH.sub.3 ##STR480## OH NH 140-143__________________________________________________________________________ TABLE 57__________________________________________________________________________Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________968 CH.sub.3 COOCH.sub.2 CHCH.sub.2 OH NH969 CH.sub.3 COOCH2C CH OH NH970 CH.sub.3 CONHCH.sub.3 ##STR481## NH971 CH.sub.3 CONHCH.sub.3 OH NH972 CH.sub.3 ##STR482## ##STR483## NH973 CH.sub.3 ##STR484## OH NH974 CH.sub.3 ##STR485## ##STR486## NH975 CH.sub.3 ##STR487## OH NH976 CH.sub.3 COSCH.sub.3 OH NH977 CH.sub.3 COSC.sub.2 H.sub.5 OH NH978 CH.sub.3 COSC.sub.3 H.sub.7 OH NH979 CH.sub.3 COSC.sub.4 H.sub.9 OH NH980 CH.sub.3 ##STR488## OH NH981 CH.sub.3 ##STR489## OH NH 172-176982 CH.sub.3 CH.sub.3 ##STR490## NH 115-118983 CH.sub.3 CH.sub.3 OH NH 168-172984 CH.sub.3 H OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t NH 52-55985 CH.sub.3 COOH OH NH 178-182986 CH.sub.3 COOCH.sub.2 OCH.sub.3 OCH.sub.2 OCH.sub.3 NH 145-148987 CH.sub.3 ##STR491## OH NH 203-206__________________________________________________________________________ TABLE 58______________________________________Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)______________________________________ 988 CH.sub.3 COOC.sub.3 H.sub.7 OCH.sub.2 CHCH.sub.2 S 989 CH.sub.3 COOC.sub.3 H.sub.7 OH S 990 CH.sub.3 COOC.sub.3 H.sub.7 -i OH S 991 CH.sub.3 COOC.sub.4 H.sub.9 OH S 992 CH.sub.3 CONHC.sub.3 H.sub.7 OH S 993 CH.sub.3 COSC.sub.2 H.sub.5 OH S 994 H COOC.sub.2 H.sub.5 OH NH 995 Cl COOC.sub.2 H.sub.5 OH NH 996 CN COOC.sub.2 H.sub.5 OH NH 997 NO.sub.2 COOC.sub.2 H.sub.5 OH NH 998 CH.sub.2 Cl COOC.sub.2 H.sub.5 OH NH 999 CH.sub.2 OH COOC.sub.2 H.sub.5 OH NH1000 CH.sub.2 OCH.sub.3 COOC.sub.2 H.sub.5 OH NH1001 H COCH.sub.3 OH NH1002 H CHO OH NH1003 H CN OH NH1004 H CH.sub.3 OH NH1005 C.sub.2 H.sub.5 COOC.sub.2 H.sub.5 OH NH1006 C.sub.2 H.sub.5 H OH NH______________________________________ TABLE 59__________________________________________________________________________ ##STR492##Com-pound m.p. (.degree.C.)No. R.sup.1 R.sup.2 R X or (n.sub.D.sup.20)__________________________________________________________________________1007 CH.sub.3 COOC.sub.3 H.sub.7 -i OCH.sub.2 O 120-121.51008 CH.sub.3 COOC.sub.3 H.sub.7 -i OCH.sub.2 CHCH.sub.2 O 1.56511009 CH.sub.3 COOC.sub.3 H.sub.7 -i OH O 188-1911010 CH.sub.3 COOCH.sub.3 OCH.sub.2 CHCH.sub.2 O 118-1221011 CH.sub.3 ##STR493## OCH.sub.2 CHCH.sub.2 NH1012 CH.sub.3 ##STR494## OH NH1013 CH.sub.3 H OH NH__________________________________________________________________________

Compounds (I) of the present invention can be produced, for example, in accordance with the following processes 1 to 6. ##STR495## (wherein L.sup.1 is a halogen atom, an alkylsulfonyl group, a benzylsulfonyl group or a substituted benzylsulfonyl group, and R, R.sup.3, R.sup.4, A, W, Y, Z and n are as defined above.)

A compound of the formula (I) can be produced by reacting a compound of the formula (II) with a compound of the formula (III) in a suitable solvent in the presence of an at least equal amount of a base at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal such as metal sodium or metal potassium, an alkali metal hydride or an alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or acetonitrile, may, for example, be used.

The condensed heterocyclic carbonyl derivative (II) as the starting material can be obtained by known methods, for example, the methods disclosed in Bulletin de la Saciete Chimique de France), p. 2763-2766 (1975), J. Indian. Chem. Soc. Vol 45 (5), p. 439-445 (1968), Indian. J. Chem. Section B, 25B (8), p. 870-871 (1986), J. Chem. Soc. Organic Chemistry (1), p. 1-4 (1969), Indian. J. Chem. Section B, 15B (91), p. 1056-1058 (1977), Pract. Heterocyclic. Chem. Academic, p. 55 (1968), Organic Reaction, Vol 20, p. 337 (1973), Helvetica Chemica Acta., Vol 54, p. 959 (1970), J. Org. Chem., Vol 33 (12), p. 4426 (1968), Chemical and Pharmaceutical Bulletin, Vol 25 (11), p. 2988 (1977), and Parmaco, Edizione Scientifica (ITA), Vol 36 (9), p. 794 (1981).

Further, in a case where R in the formula (II) is H, a product wherein R is OH can be obtained by oxidation in accordance with a known method. ##STR496## (wherein R.sup.21 is an alkyl group, an allyl group, a benzyl group or a trimethylsilylethyl group, and A, W, Y, Z, R.sup.3, R.sup.4 and n are as defined above.)

When R.sup.21 is an alkyl group, a compound of the formula (V) can be produced by reacting a compound of the formula (IV) in water or in a suitable solvent containing water in the presence of an at least equimolar amount of a base at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours, followed by acidifying.

As the base, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, may be used.

As the solvent, an alcohol solvent such as methanol, ethanol or 2-propanol, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or diemthylsulfoxide, or other solvent such as acetonitrile, may, for example, be used.

When R.sup.21 is an allyl group, a product can be produced by reacting such a compound with dimedone or with an allyl acceptor such as formic acid or n-butylamine in a solvent such as acetonitrile, diemthylformamide or tetrahydrofuran using a palladium catalyst such as tetrakistriphenylphosphine palladium (O) at a temperature within a range of from room temperature to the boiling point of the solvent for from 1 to 24 hours.

Further, when R.sup.21 is a benzyl group, a product can be produced by hydrogenation in a suitable solvent using a platinum catalyst or palladium catalyst at an ordinary temperature under an ordinary pressure (if required, under heating and under pressure).

When R.sup.21 is a trimethylsilylethyl group, a product can be produced by reacting such a material with an at least equimolar amount of tetrabutylammonium fluoride or the like in tetrahydrofuran at room temperature.

As the solvent, an alcohol solvent such as methanol or ethanol, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such a.s acetone or methyl ethyl ketone, an ether solvent such as diethyl ether, 5 dioxane or tetrahydrofuran, or acetic acid, may, for example, be used. ##STR497## {wherein Q is a halogen atom, a cyano group, or an imidazolyl group, R.sup.22 is an alkoxy group which may be substituted, a benzyloxy group which may be substituted, an isopropylidenaminoxy group, a phenyloxy group which may be substituted, a phenylthio group which may be substituted, an alkenyloxy group, an alkynyloxy group, an alkylthio group, or a group of the formula --NR.sup.6 R.sup.7 (wherein each of R.sup.6 and R.sup.7 which may be the same or different, is a hydrogen atom, an alkyl group, a phenyl group which may be substituted, an alkylsulfonyl group, or a phenylsulfonyl group which may be substituted, or R.sup.6 and R.sup.7 may, together with the nitrogen atom, form a ring ), and R.sup.3, R.sup.4, A, W, Y, Z and n are as defined above.}

For the production of a compound of the formula (I) of the present invention, a compound of the formula (V) is reacted with an at least equimolar amount of a condensing agent in a suitable solvent at a temperature within a range of from -10.degree. C. to the boiling point of the solvent for from 0.5 to 24 hours to obtain a compound of the formula (VI). After isolating or without isolating it, it is reacted with a compound of the formula (VII) together with an at least equimolar amount of a base in a suitable solvent at a temperature within a range of from -10.degree. C. to the boiling point of the solvent for from 0.5 to 24 hours, to obtain a compound of the formula (I).

As the condensing agent, thionyl chloride, oxalic acid dichloride, a chlorocarbonic acid ester, carbonyl diimidazole, a cyanophospholic acid ester or a carbodiimide may, for example, be used.

As the base, an alkali metal such as metal sodium or metal potassium, an alkali metal hydride or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may, for example, be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used. ##STR498## (wherein R.sup.3, R.sup.4, A, W, Y, Z and n are as defined above, and M is an alkali metal, an alkaline earth metal, ammonium or organic ammonium.)

A compound of the formula (VIII) can be produced by reacting the compound of the formula (V) together with an equimolar amount of a base in a suitable solvent at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal hydroxide or alkaline earth metal hydroxide such as sodium hydroxide or calcium hydroxide, an alkali metal carbonate or alkaline earth metal carbonate such as sodium carbonate or calcium carbonate, an alkali metal hydride or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as sodium methoxide or sodium ethoxide, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, ammonia, or an organic amine such as isopropylamine, may, for example, be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ester solvent such as methyl acetate or ethyl acetate, an alcohol solvent such as methanol, ethanol or 2-propanol, an ether solvent such as diethyl ether, tetrahydrofuran or dioxane, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile or water, may, for example, be used. ##STR499## (wherein A, R.sup.3, R.sup.4, W, Y, Z and n are as defined above.)

The compound of the formula (V) of the present invention can be obtained by reacting the compound of the formula (IX) with a suitable oxidizing agent in a suitable solvent at a temperature within a range of from 0.degree. C. to the boiling point of the solvent for from 0.5 to 24 hours.

As the oxidizing agent, a permanganate such as potassium permanganate, a chromic acid such as chromic anhydride, hydrogen peroxide, an organic peracid such as n-chloroperbenzoic acid, or nickel peroxide, may, for example, be used. As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile or water, may, for example, be used. ##STR500## (wherein R.sup.23 is an alkyl group which may be substituted, a benzyl group which may be substituted, an alkenyl group, an alkynyl group, or a 2-trimethylsilylethoxymethyl group, L.sup.2 is a hydrogen atom, and R.sup.3, R.sup.4, A, W, Y, Z and n are as defined above.)

A compound of the formula (XI) can be produced by reacting a compound of the formula (V) with a compound of the formula (X) in a suitable solvent in the presence of a base at a temperature within a range of from 10.degree. C. to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, or an alkali metal hydride such as sodium hydride, may, for example, be used.

As the solvent, a ketone solvent such as acetone or methyl ethyl ketone, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used. ##STR501## (wherein L.sup.3 is a leaving group such as a halogen, and R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, W and Z are as defined above, provided that R.sup.5 excludes a hydrogen atom.)

A compound of the formula (XIV) can be produced by reacting a compound of the formula (XII) with a compound of the formula (XIII) in a suitable solvent in the presence of an at least equimolar amount of a base at a temperature within a range of from -10.degree. C. to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal such as metal sodium or metal potassium, an alkali metal hydride such as sodium hydride or potassium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may, for example, be used.

As the solvent, a hydrocarbon solvent such as toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether or tetrahydrofuran, a ketone solvent such as acetone, an aprotic polar solvent such as N,N-dimethylformamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used. ##STR502## (wherein R.sup.24 is a formyl group or a nitro group, and R.sup.1, R.sup.3, R.sup.4, R, W, Y, Z and n are as defined above.)

A compound of the formula (XVI) can be obtained by subjecting the compound of the formula (XV) to a Vilsmeier reaction with phosphorus oxychloride in N,N-dimethylformamide to obtain a formyl product, or reacting it with a nitric acid ester in tetrahydrofuran in the presence of an alcoholate or reacting it with nitronium tetrafluoroborate in acetonitrile or in tetrahydrofuran at a temperature within a range of from -50.degree. C. to the boiling point of the solvent, to obtain a nitro product.

Further, the obtained nitro product may be reduced by a conventional method to obtain an amino product, which can be led to various derivatives.

Among the compounds of the formula (I) of the present invention wherein A is (A-11), a compound of the formula (XIX) can be produced by the following process. ##STR503## (wherein X.sup.1 and X.sup.2 represent an oxygen atom, a sulfur atom and NR.sup.14 among those defined above, R, R.sup.3, R.sup.4, R.sup.14, Q.sup.1, W, Y, Z and n are as defined above, each of R.sup.25 and R.sup.26 which may be the same or different, is a chlorine atom, an alkoxy group or a lower alkylthio group.)

A compound of the formula (XIX) can be produced by reacting a compound of the formula (XVII) with a compound of the formula (XVIII) in a suitable solvent in the presence or absence of a base at a temperature within a range of from -30.degree. C. to the boiling point of the solvent, preferably from 0.degree. C. to 120.degree. C., for from 0.5 to 24 hours.

As the base to be used, preferred is an organic base such as triethylamine, pyridine, N,N-diisopropylethylamine or N,N-dimethylaniline. However, an alkali metal hydride or an alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, may also be used.

As the solvent to be used, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylacetamide, N,N-dimethylformamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be employed.

Among the compounds of the formula (I) of the present invention wherein A is (A-12), a compound of the formula (XII) can be produced by the following process. ##STR504## (wherein R.sup.5, R.sup.18 and R.sup.19 represent a hydrogen atom and a lower alkyl group among those defined above, X.sup.2 represents an oxygen atom, a sulfur atom and NR.sup.14 among those defined above, L.sup.4 is a chlorine atom or a bromine atom, and R, R.sup.3, R.sup.4, R.sup.14, W. Y, Z and n are as defined above.)

A compound of the formula (XXII) can be produced by reacting a compound of the formula (XX) with a compound of the formula (XXI) in a suitable solvent in the presence of a base at a temperature within a range of from 0.degree. C. to the boiling point of the solvent, preferably from 10.degree. C. to 80.degree. C., for from 1 to 20 hours.

As the base to be used, an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, an alkali metal hydride or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal alkoxide such as potassium t-butoxide, or an organic base such as triethylamine, pyridine, N,N-diisopropylethylamine or N,N-dimethylaniline, may, for example, be employed.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylacetamide, N,N- dimethylformamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used.

Among the compounds of the formula (I) wherein A is (A-12), a compound of the formula (XXVI) can be produced in accordance with the following process. ##STR505## (wherein R.sup.27 is a group of the formula CR.sup.18 R.sup.19 (--CH.dbd.CHR.sup.18 or a group of the formula CR.sup.18 R.sup.19 C.tbd.CR.sup.18, R.sup.18 and R.sup.19 represent a hydrogen atom and a lower alkyl group among those defined above, X.sup.1 represents an oxygen atom, a sulfur atom and NR.sup.14 among those defined above, and L.sup.4, R, R.sup.3, R.sup.4, R.sup.14, W, Y, Z and n are as defined above.)

A compound of the formula (XXV) can be produced by reacting a compound of the formula (XXIII) with a compound of the formula (XXIV) in a suitable solvent in the presence of a base at a temperature within a range of from 0.degree. C. to the boiling point of the solvent, preferably from 20.degree. C. to 80.degree. C., for from 1 to 24 hours.

As the base and the solvent to be used, the same as those described for Process 6 may be employed.

Further, a compound of the formula (XXVI) can be produced by subjecting a compound of the formula (XXV) to an intramolecular cyclization reaction in a suitable solvent in the presence of a suitable catalyst at a temperature of from 0.degree. C. to the boiling point of the solvent, preferably from 20.degree. C. to 150.degree. C., for from 5 to 72 hours.

As the catalyst to be used, an alkali metal carbonate such as potassium carbonate or sodium carbonate, or silver oxide (yellow), may, for example, be mentioned.

As the solvent to be used, preferred is an alcohol solvent such as methanol or ethanol, or an aprotic polar solvent such as N,N-dimethylacetamide, N,N-dimethylformamide or dimethylsulfoxide. However, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, or other solvent such as acetonitrile, may also be used.

Among the compounds of the formula (I) of the present invention wherein A is (A-12), a compound of the formula (XXX) can be produced by the following process. ##STR506## (wherein R.sup.18 and R.sup.19 represent a hydrogen atom and a lower alkyl group among those defined above, X.sup.1 represents an oxygen atom, a sulfur atom and NR.sup.14 among those defined above, and L.sup.4, R, R.sup.3, R.sup.4, R.sup.14, W, Y, Z and n are as defined above.)

A compound of the formula (XXIX) can be produced by reacting a compound of the formula (XXVII) with a compound of the formula (XXVIII) in a suitable solvent in the presence of a base at a temperature within a range of from 0.degree. C. to the boiling point of the solvent, preferably from 20.degree. C. to 80.degree. C., for from 3 to 24 hours. In this case, the reaction may be accelerated by an addition of an alkali metal iodide such as potassium iodide, as the case requires.

The base and the solvent to be used may be the same as those as described for Process 6.

Further, a compound of the formula (XXX) can be produced by subjecting a compound of the formula (XXIX) to hydrogenation in a suitable solvent in the presence of a palladium carbon catalyst at an ordinary temperature under an ordinary pressure for from 3 to 72 hours.

As the solvent to be used, preferred is an alcohol solvent such as methanol or ethanol. However, a hydrocarbon solvent such as benzene, toluene or xylene, an ether solvent such as tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, or other solvent such as acetonitrile, may also be used.

Among the compounds of the formula (I) of the present invention wherein A is (A-12), a compound of the formula (XXXIV) can be produced by the following process. ##STR507## (wherein R.sup.18 and R.sup.19 represent a hydrogen atom and a lower alkyl group among those defined above, X.sup.1 represents an oxygen atom, a sulfur atom and NR.sup.14 among those defined above, and L.sup.4, R, R.sup.3, R.sup.4, R.sup.14, W, Y. Z and n are as defined above.)

A compound of the formula (XXXII) can be produced by reacting a compound of the formula (XXVII) with a compound of the formula (XXXI) in a suitable solvent in the presence of a base at a temperature within a range of from 0.degree. C. to the boiling point of the solvent, preferably from 20.degree. C. to 80.degree. C., for from 5 to 24 hours. In this case, the reaction may be accelerated by an addition of an alkali metal iodide such as potassium iodide, as the case requires.

A compound of the formula (XXXIII) can be produced by subjecting a compound of the formula (XXXIV) to an intramolecular cyclization reaction in a suitable solvent in the presence of a base at a temperature within a range of from 0.degree. C. to the boiling point of the solvent, preferably from 20.degree. C. to 80.degree. C., for from 5 to 24 hours.

The base and the solvent to be used may be the same as those described for Process 6.

Further, a compound of the formula (XXXIV) can be produced by reducing a compound of the formula (XXXIII) in a suitable solvent using sodium hydrosulfite at a temperature within a range of from 0.degree. C. to the boiling point of the solvent, preferably from 30.degree. C. to 50.degree. C., for from 0.1 to 1 hour.

As the solvent to be used, preferred is an alcohol solvent such as methanol or ethanol, or water. However, an ether solvent such as tetrahydrofuran or 1,4-dioxane, a ketone solvent such as acetone or methyl ethyl ketone, or other solvent such as acetonitrile, may be used in combination, as the case requires.

Now, the processes for the production of the compounds of the present invention, as well as methods for preparation of formulations and methods for application will be specifically described with reference to Examples.

BEST MODE FOR CARRYING OUT THE INVENTION

EXAMPLE 1

Preparation of 5-(4, 6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene (Compound No. 104)

A mixture comprising 2.1 g of 4-formyl-5-hydroxy-3-methylbenzothiophene, 2.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.8 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 70.degree. C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 3.1 g (yield: 86%) of the desired compound.

EXAMPLE 2

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-methylbenzothiophene-4-carboxylic acid (Compound No. 105)

0.6 g of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene was dissolved in 80 ml of acetone. While stirring the solution at room temperature, 0.6 g of potassium permanganate dissolved in 10 ml of water was dropwise added thereto over a period of 15 minutes, and the mixture was further stirred at room temperature for 4 hours. It was then concentrated under reduced pressure to remove acetone, and then a saturated sodium bicarbonate aqueous solution was added thereto to make the mixture alkaline. The mixture was extracted with ethyl acetate, and then the aqueous layer was precipitated with 10% hydrochloric acid. The precipitated crystals were collected by filtration and washed with water to obtain 0.47 g (yield: 76%) of the desired compound.

EXAMPLE 3

Preparation of benzyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 1)

A mixture comprising 12.88 g of benzyl 3-ethoxycarbonyl-5-hydroxy-2-methylbenzofuran-5-carboxylate, 8.33 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 5.53 g of potassium carbonate in 150 ml of N,N-dimethylformamide, was heated and stirred at 70.degree. C. for 3 hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 14.45 g (yield: 81%) of the desired compound.

EXAMPLE 4

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylic acid (Compound No. 2)

A mixture comprising 14.4 g of benzyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate and 4.52 g of 10% palladium carbon in 100 ml of ethanol, was subjected to hydrogenation under an ordinary pressure while stirring at room temperature. After completion of the reaction, an insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure, whereupon the precipitated crystals were washed with a solvent mixture of diethyl ether/n-hexane to obtain 10.47 g (yield: 89%) of the desired compound.

EXAMPLE 5

Preparation of pivaloyloxymethyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 4)

A mixture comprising 0.40 g of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylic acid, 0.26 g of chloromethyl pivalate and 0.21 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was stirred at room temperature for 6 hours, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 0.43 g (yield: 84%) of the desired compound.

EXAMPLE 6

Preparation of methyl 5-(4,6-dimethoxypyrimidin-2-yl) oxybenzoxazol-4-carboxylate (Compound No. 446) A mixture comprising 0.6 g of methyl 5-hydroxybenzoxazol-4-carboxylate, 0.6 g of 2-chloro-4,6-dimethoxypyrimidine and 0.7 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 115.degree. C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate =5/1) to obtain 0.4 g (yield: 39%) of the desired compound.

EXAMPLE 7

Preparation of methyl 6-(4, 6-dimethoxy-1,3,5-triazin-2-yl)oxybenzoxazol-7-carboxalate (Compound No. 464)

0.6 g of methyl 6-hydroxyybenzoxazol-7-carboxylate, 0.55 g of 2-chloro-4,6-dimethoxy-1,3,5-triazine and 0.5 g of potassium carbonate in 30 ml of N,N-dimethylformamide were heated and stirred at 115.degree. C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) to obtain 0.6 g (yield: 58%) of the desired compound.

EXAMPLE 8

Preparation of methyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate (Compound No. 507)

A mixture comprising 1.0 g of methyl 2-ethoxy-5-hydroxy-2,3-dihydrobenzofuran-4-carboxylate, 1.0 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.78 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 100.degree. C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate =4/1) to obtain 1.5 g (yield; 95%) of the desired compound.

EXAMPLE 9

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylic acid (Compound No. 508)

While stirring 1.2 g of methyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate in 20 ml of dimethylsulfoxide at room temperature, 2 ml of a 2N sodium hydroxide aqueous solution was dropwise added thereto over a period of 10 minutes and then the mixture was further stirred for 15 hours. The mixture was poured into water and extracted with diethyl ether. Then, the aqueous layer was acidified with 10% hydrochloric acid, and precipitated crystals were extracted with ethyl acetate, and the organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 1.0 g (yield: 87%) of the desired compound.

EXAMPLE 10

Preparation of sodium 3-benzoyl-5-(4, 6-dimethoxypyrimidin-2-yl) oxy-2-trifluoromethylbenzofuran-4-carboxylate (Compound No. 77)

While stirring 0.35 g of sodium hydride in 30 ml of N,N-dimethylformamide at room temperature, 1.73 g of 3-benzoyl-5-hydroxy-2-trifluoromethylbenzofuran-4-carboxylic acid was gradually added thereto. After completion of the addition, the mixture was further stirred for one hour. While stirring this mixture at room temperature, 1.08 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine was added thereto, and then the mixture was stirred at 70.degree. C. for 3 hours. The mixture was returned to room temperature and poured into water. Precipitated crystals were separated by filtration and washed with water and acetone to obtain 1.02 g (yield: 40.5%) of the desired compound.

EXAMPLE 11

Preparation of benzyl 5-(4,6-dimethoxy-1,3, 5-triazin-2-yl)oxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylate (Compound No. 32)

A mixture comprising 2 g of benzyl 5-hydroxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylate, 1 g of 4,6-dimethoxy-2-methylsulfonyl-1,3,5-triazine and 1 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at 70.degree. C. for two hours. The mixture was returned to room temperature, poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the obtained solid was thoroughly washed with ethanol to obtain 2.4 g (yield: 86%) of the desired compound.

EXAMPLE 12

Preparation of methyl 6-(4,6-dimethoxypyrimidin-2-yl) oxy-3-methyl-benzisoxazol-7-carboxylate (Compound No. 487)

A mixture comprising 1.3 g of methyl 6-hydroxy-3-methyl-benzisoxazol-7-carboxylate, 1.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at 70.degree. C. for two hours. The mixture was returned to room temperature, poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the obtained crystals were thoroughly washed with isopropyl ether to obtain 1.6 g (yield: 73%) of the desired compound.

EXAMPLE 13

Preparation of 6-(4,6-dimethoxypyrimidin-2-yl) oxy-3-methyl-benzisoxazol-7-carboxylic acid (Compound No. 488)

While heating and stirring 1.0 g of methyl 6-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methylbenzisoxazol-7-carboxylate in 20 ml of N,N-dimethylsulfoxide at 70.degree. C., 1.7 ml of a 2N sodium hydroxide aqueous solution was dropwise added thereto over a period of 10 minutes. Then, the mixture was further heated and stirred at 70.degree. C. for 30 minutes. The mixture was returned to room temperature, then poured into water and extracted with diethyl ether. The aqueous layer was acidified with 10% hydrochloric acid, and precipitated crystals were extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was then concentrated under reduced pressure, and the crystals thereby obtained were washed with isopropyl ether to obtain 0.7 g (yield: 71%) of the desired compound.

EXAMPLE 14

Preparation of sodium 6-(4,6-dimethoxypyrimidin-2-yl) oxy-3-methoxycarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 130)

While stirring 0.5 g of 5-(4, 6-dimethoxypyrimidin-2-yl) oxy-3-methoxycarbonyl-2-methyl-benzofuran-4-carboxylic acid in 5 ml of tetrahydrofuran at room temperature, 0.05 g of 60% sodium hydride was added thereto. The mixture was stirred at room temperature for 6 hours. Then, precipitated crystals were collected by filtration and washed with isopropyl ether to obtain 0.40 g (yield: 75%) of the desired compound.

EXAMPLE 15

Preparation of N-�5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carbonyl!imidazole (Compound No. 16)

While stirring 0.8 g of 5-(4, 6-dimethoxypyrimidin-2-yl) oxy-3-ethoxycarbonyl-2-methyl-benzofuran-4-carboxylic acid in 30 ml of tetrahydrofuran at room temperature, 0.36 g of carbonyldiimidazole was added thereto. The mixture was stirred at room temperature for one hour and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water. It was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the crystals thereby obtained were washed with n-hexane to obtain 0.81 g (yield: 90%) of the desired compound.

EXAMPLE 16

Preparation of 4-allyloxycarbonyl-5-(4, 6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carboxylic acid (Compound No. 371)

A mixture comprising 54.2 g of 4-allyloxycarbonyl-5-hydroxy-2-methylbenzofuran-3-carboxylic acid, 47 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 65 g of potassium carbonate in 200 ml of N,N-dimethylformamide, was heated and stirred at 70.degree. C. for two hours. The mixture was returned to room temperature, and then the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Crystals obtained by concentration under reduced pressure, were washed with isopropyl ether to obtain 79.2 g (yield: 98%) of the desired compound.

EXAMPLE 17

Preparation of 4-allyloxycarbonyl-5-(4, 6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-2-carbonyl chloride (Compound No. 254)

30.4 g of 4-allyloxycarbonyl-5-(4, 6-dimethoxypyrimidin-2-yl) oxy-2-methylbenzofuran-3-carboxylic acid was dissolved in 73 ml of thionyl chloride, and the solution was heated and stirred at 60.degree. C. for 30 minutes. It was returned to room temperature, and then thionyl chloride was concentrated under reduced pressure. Toluene was added thereto, followed by further concentration. To the obtained oily substance, hexane was added for crystallization to obtain 31.4 g (yield: 99%) of the desired compound.

EXAMPLE 18

Preparation of allyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylate (Compound No. 248)

3.0 g of 4-allyloxycarbonyl-5-(4, 6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carbonyl chloride was dissolved in 13 ml of dichloromethane, and 1.5 g of a 50% dimethylamine aqueous solution was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The oily substance obtained by concentration under reduced pressure, was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 1.84 g (yield; 60%) of the desired compound.

EXAMPLE 19

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylic acid (Compound No. 247)

1.40 g of allyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylate and 0.29 g of formic acid were dissolved in 12 ml of tetrahydrofuran, and 37 mg of tetrakistriphenylphosphine palladium (0) was added thereto under a nitrogen atmosphere. The mixture was heated and stirred at 50.degree. C. for 3 hours. The mixture was returned to room temperature, and then isopropyl ether was added to the reaction solution. Precipitated crystals were collected by filtration to obtain 1.02 g (yield: 80%) of the desired compound.

EXAMPLE 20

Preparation of allyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 152)

3.0 g of 4-allyloxycarobnyl-5-(4, 6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carbonyl chloride and 0.88 g of triethylamine were dissolved in 13 ml of dichloromethane, and 0.56 g of ethyl mercaptan was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate =4/1) to obtain 1.74 g (yield: 55%) of the desired compound.

EXAMPLE 21

Preparation of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylic acid (Compound No. 153)

1.60 g of allyl 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylate and 0.54 g of dimedone were dissolved in 14 ml of tetrahydrofuran, and 40 mg of tetrakistriphenylphosphine palladium (0) was added thereto under a nitrogen atmosphere. The mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1) to obtain 1.33 g (yield: 91%) of the desired compound.

EXAMPLE 22

Preparation of 2-trimethylsilylethoxymethyl 5-(4, 6-dimethoxypyrimidin-2-yl) oxy-3-(4-methoxybenzyloxycarbonyl)-2-methylbenzofuran-4-carboxylate (Compound No. 369) 13.5 g of 5-(4,6-dimethoxypyrimidin-2-yl) oxy-3-(4-methoxybenzyloxycarbonyl)-2-methylbenzofuran-4-carboxylic acid and 3.3 g of triethylamine were dissolved in 120 ml of dichloromethane, and 5.0 g of 2-trimethylsilylethoxymethyl chloride was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate =4/1) to obtain 14.0 g (yield: 82%) of the desired compound.

EXAMPLE 23

Preparation of methyl 6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!quinolin-5-carboxylate (Compound No. 904)

0.8 g of methyl 6-hydroxyquinolin-5-carboxylate, 0.96 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 0.82 g of potassium carbonate were stirred in 30 ml of N,N-dimethylformamide at 80.degree. C. for 3 hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from a solvent mixture of dichloromethane/isopropyl ether to obtain 1.21 g (yield: 89.0%) of the desired compound. mp: 160.degree.-162.degree. C.

EXAMPLE 24

Preparation of 6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!quinolin-5-carboxylic acid (Compound No. 903)

0.8 g of methyl 6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!quinolin-5-carboxylate was dissolved in 10 ml of methanol and 20 ml of methoxyethane, and 5 ml of an aqueous solution containing 0.39 g of potassium hydroxide was added thereto at 40.degree. C. The mixture was extracted with dichloromethane. The aqueous layer was acidified (pH=4) with a 10% hydrochloric acid aqueous solution, and formed precipitates were collected by filtration and dried to obtain 0.5 g (yield: 66.0%) of the desired compound. mp: 195.degree.-198.degree. C.

EXAMPLE 25

Preparation of benzyl 5-�(4, 6-dimethoxypyrimidin-2-yl) oxy!2-methylindol-4-carboxylate (Compound No. 664)

A mixture comprising 2.2 g of benzyl 5-hydroxy-2-methylindol-4-carboxylate, 1.7 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.3 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at a temperature of from 70.degree. to 80.degree. C. for two hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2.8 g (yield: 85%) of the desired product. mp: 135.degree.-139.degree. C.

EXAMPLE 26

Preparation of benzyl 5-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-3-formyl-2-methylindol-4-carboxylate (Compound No. 680)

0.46 ml of phosphorus oxychloride was dropwise added to 1.8 ml of N,N-dimethylformamide under cooling with ice, and the mixture was stirred for 30 minutes. Then, 2.3 g of benzyl 5-�(4,6-dimethoxypyrimidin-2-yl) oxy!-2-methylindol-4-carboxylate was dissolved in 10 ml of N,N-dimethylformamide, and the solution was dropwise added to the above mixture under cooling with ice. The mixture was stirred for 30 minutes, and then poured into ice water. An aqueous sodium hydroxide solution was added thereto for adjustment to pH9, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2 g (yield: 81.5%) of the desired compound. mp: 148.degree.-149.degree. C.

EXAMPLE 27

Preparation of allyl 5-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-2-methyl-3-nitroindol-4-carboxylate (Compound No. 759)

2.0 g of allyl 5-�(4, 6-dimethoxypyrimidin-2-yl)oxy!-2-methylindol-4-carboxylate was dissolved in 25 ml of acetonitrile, and the solution was cooled to -30.degree. C. 16.3 ml of a 0.5M sulfolane solution of nitronium tetrafluoroborate was dropwise added thereto, and the mixture was stirred for 5 hours. After adding 2 ml of aqueous ammonia, the mixture was returned to room temperature and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Crystals obtained by concentration under reduced pressure, were washed with hexane to obtain 1.23 g (yield: 55%) of the desired compound.

EXAMPLE 28

Preparation of allyl 3-amino-5-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-2-methylindol-4-carboxylate (Compound No. 722)

3.4 g of allyl 5-�(4,6-dimethoxypyrimidin-2-yl) oxy!-2-methyl-3-nitroindol-4-carboxylate was dissolved in 50 ml of methanol, and 5 ml of concentrated hydrochloric acid was added thereto. Then, 4.9 g of tin powder was gradually added at room temperature. Them, the mixture was stirred at room temperature for 12 hours. The solid was filtered off, and then residue was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2.5 g (yield: 79%) of the desired product. mp: 132.degree.-135.degree. C.

EXAMPLE 29

Preparation of allyl 3-acetylamino-5-�(4, 6-dimethoxypyrimidin-2-yl)oxy!-2-methylindol-4-carboxylate (Compound No. 735)

0.5 g of allyl 5-�(4,6-dimethoxypyrimidin-2-yl) oxy!-2-methylindol-4-carboxylate was dissolved in 10 ml of pyridine, and 0.16 g of acetic anhydride was added thereto. The mixture was stirred for 12 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized with isopropyl ether to obtain 0.49 g (yield: 87%) of the desired compound. mp: 177.degree.-180.degree. C.

EXAMPLE 30

Preparation of 3-acetylamino-5-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-2-methylindol-4-carboxylic acid (Compound No. 736)

0.49 g of allyl 3-acetylamino-5-�(4, 6-dimethoxypyrimidin-2-yl)oxy!-2-methylindol-4-carboxylate was dissolved in 10 ml of tetrahydrofuran, and 0.1 g of dimedone and 0.01 g of tetrakistriphenylphosphine palladium were added thereto. The mixture was stirred at room temperature for 4 hours. Crystals obtained by concentration under reduced pressure, was washed with isopropyl ether to obtain 0.41 g (yield: 93%) of the desired compound. mp: 230.degree.-233.degree. C.

EXAMPLE 31

Preparation of benzyl-l-benzoyl-5-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-3-ethoxycarbonyl-2-methylindol-4-carboxylate (Compound No. 796)

1.5 g of benzyl 5-�(4,6-dimethoxypyrimidin-2-yl) oxy!-3-ethoxycarbonyl-2-methylindol-4-carboxylate was dissolved in 50 ml of tetrahydrofuran, and 0.176 g of 60% sodium hydride was added thereto. The mixture was stirred at room temperature for 30 minutes. Then, 0.51 g of benzoyl chloride was dropwise added thereto at room temperature, and the mixture was stirred for 4 hours. After concentration under reduced pressure, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 1.67 g (yield: 92%) of the desired compound. mp: 128.degree.-132.5.degree. C.

EXAMPLE 32

Preparation of l-benzoyl-5-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-3-ethoxycarbonyl-2-methylindol-4-carboxylic acid (Compound No. 797)

1.6 g of benzyl 1-benzoyl-5-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-3-ethoxycarbonyl-2-methylindol-4-carboxylate was dissolved in 50 ml of ethyl acetate, and 0.1 g of 10% palladium carbon was added thereto. Then, catalytic reduction was conducted. Insoluble matters were filtered off, and then filtrate was concentrated under reduced pressure. The residue thereby obtained was washed with isopropyl ether to obtain 1.28 g (yield: 97%) of the desired compound. mp: 113.degree.-115.degree. C.

EXAMPLE 33

Preparation of (2-trimethylsilyl)ethyl 6-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-2-oxobenzoxazolin-7-carboxylate (Compound No. 853)

1.18 g of triphosgene was gradually added at room temperature to a mixture comprising 2.45 g of (2-trimethylsilyl)ethyl 3-amino-2-hydroxy-6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate and 5 ml of triethylamine in 20 ml of dichloromethane. The mixture was stirred at room temperature for one hour, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, 10% hydrochloric acid and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 2.25 g (yield: 97%) of the desired compound. (Yield: 86.5%) Refractive index: unmeasurable

EXAMPLE 34

Preparation of (2-trimethylsilyl)ethyl 7-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-3-oxo-3,4-dihydro-2H-1,4-benzooxadin-8-carboxylate (Compound No. 878)

0.60 g of chloroacetyl chloride was gradually dropwise added at 10.degree. C. to a mixture comprising 2.04 g of (2-trimethylsilyl)ethyl 3-amino-2-hydroxy-6-�(4,6-dimethoxypyrimidin-2-yl) oxy!benzoate and 1.38 g of potassium carbonate in 15 ml of N,N-dimethylformamide, and then the mixture was gradually returned to room temperature and stirred for 5 hours. Further, the mixture was stirred at 50.degree. C. for two hours to complete the reaction. The mixture was returned to room temperature, then poured into water, adjusted to pH3 with 10% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 1.01 g (yield: 41.8%) of the desired compound. mp: 148.degree.-150.degree. C.

EXAMPLE 35

Preparation of (2-trimethylsilyl)ethyl 7-�(4, 6-dimethoxypyrimidin-2-vl) oxy!-2-methylene-3, 4-dihydro-2H-1,4-benzoxadin-8-carboxylate (Compound No. 896)

A mixture comprising 4.20 g of (2-trimethylsilyl)ethyl 3-amino-2-hydroxy-6-�(4, 6-dimethoxypyrimidin-2-yl) oxy!benzoate, 1.68 g of sodium carbonate and 1.42 g of propargyl bromide in 20 ml of N,N-dimethylformamide was heated and stirred at 50.degree. C. for 4 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 2.90 g (yield: 63.9%) of (2-trimethylsilyl) ethyl 2-hydroxy-3-propargylamino-6-�(4, 6-dimethoxypryrimidin-2-yl)oxy!benzoate.

A mixture comprising 2.80 g of (2-trimethylsilyl)ethyl 2-hydroxy-3-propargylamino-6-�(4, 6-imethoxypyrimidin-2-yl)oxy!benzoate thus obtained and 0.20 g of mercury oxide (yellow) in 10 ml of N,N-imethylfromamide was heated and stirred under a nitrogen stream at 150.degree. C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 1.80 g of the desired compound. Refractive index: unmeasurable

EXAMPLE 36

Preparation of (2-trimethylsilyl)ethyl 7-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-3-methyl-3,4-dihydro-2H-1,4-benzooxadin-8-carboxylate (Compound No. 890)

1.20 g of chloroacetone was gradually dropwise added at 10.degree. C. to a mixture comprising 3.50 g of (2-trimethylsilyl) ethyl 2-hydroxy-3-nitro-6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate, 1.80 g of potassium carbonate and 1.33 g of potassium iodide in 20 ml of acetone. Then, mixture was gradually returned to room temperature and stirred for 8 hours. Insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure, poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 3.70 g (yield: 63.9%) of (2-trimethylsilyl)ethyl 2-acetonyloxy-3-nitro-6-�(4,6-dimethoxypyrimidin-2-yl) oxy!benzoate (yield: 93.7%)

3.60 g of (2-trimethylsilyl) ethyl-2-acetonitrileoxy-3-nitro-6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate thus obtained was subjected to catalytic reduction under an ordinary pressure in 100 ml of methanol by means of 0.5 g of 10% palladium carbon. The reaction was terminated when the theoretical amount of about 700 ml of hydrogen was consumed. Palladium carbon was filtered off, and the filtrate was concentrated under reduced pressure. The residue thereby obtained was purified by silica gel column chromatography to obtain 3.10 g (yield: 94.8%) of the desired compound. Refractive index: unmeasurable

EXAMPLE 37

Preparation of (2-trimethylsilyl)ethyl 7-�(4, 6-dimethoxypyrimidin-2-yl) oxy!-3,4-dihydro-2H-1,4-benzooxadin-8-carboxylate (Compound No. 884)

A mixture comprising 3.50 g of (2-trimethylsilyl)ethyl 2-hydroxy-3-nitro-6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate, 3.40 g of potassium carbonate and 9.40 g of 1,2-dibromoethane in 20 ml of N,N-dimethylformamide was heated and stirred at 80.degree. C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 3.60 g (yield: 82.8%) of (2-trimethylsilyl)ethyl 2-(2-bromoethoxy)-3-nitro-6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate. 3.60 g of (2-trimethylsilyl)ethyl 2-(2-bromoethoxy-3-nitro-6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate thus obtained and 7.00 g of 70% sodium hydrosulfite in a solvent mixture of water (15 ml) and methanol (30 ml) were stirred at room temperature for 20 minutes. The mixture was poured into water, saturated with sodium chloride and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and then extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. 3.10 g of (2-trimethylsilyl)ethyl 3-amino-2-(2-bromoethoxy)-6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate was obtained by concentration under reduced pressure. This product was used for the next reaction without purification. (Yield: 91.2%)

3.10 g of (2-trimethylsilyl)ethyl 3-amino-2-(2-bromoethoxy)-6-�(4, 6-dimethoxypyrimidin-2-yl)oxy!benzoate and 2.76 g of potassium carbonate in 10 ml of N,N-dimethylformamide were stirred at a temperature of from 60.degree. C. to 80.degree. C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. 1.95 g (yield: 75.0%) of the desired compound was obtained by concentration under reduced pressure. Refractive index: 1.5333

EXAMPLE 38

Preparation of 7-�(4,6-dimethoxypyrimidin-2-yl) oxy!-3,4-dihydro-2H-1,4-benzoxadin-8-carboxylic acid (Compound No. 885)

15 ml of 1M tetrahydrofuran solution of tetrabutylammonium fluoride trihydrate was added to 1.65 g of (2-trimethylsilyl)ethyl 7-�(4,6-dimethoxypyrimidin-2-yl) oxy!-3,4-dihydro-2H-1,4-benzoxadin-8-carboxylate obtained in Example 39 in 30 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 3 hours. The mixture was concentrated under reduced pressure, poured into water, adjusted to pH5 with a 20% citric acid aqueous solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 0.87 g (yield: 68.5%) of the desired compound. mp: 160.degree.-164.degree. C.

The herbicide of the present invention comprises a condensed heterocyclic derivative of the formula (I) as an active ingredient.

For the compound of the present invention to be used as a herbicide, the compound of the present invention may be used by itself. However, it may be used in the form of a formulation such as a dust, a wettable powder, an emulsifiable concentrate, a microgranule or a granule by blending it with a carrier which is commonly used for formulations, a surfactant, a dispersant or an adjuvant.

The carrier to be used for such formulations, may, for example, be a solid carrier such as Jeaklite, talc, bentonite, clay, kaolin, diatomaceous earth, fine silica, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate or urea, or a liquid carrier such as isopropyl alcohol, xylene, cyclohexane or methylnaphthalene.

As the surfactant and dispersant, a metal salt of alkylbenzenesulfonic acid, a metal salt of dinaphthylmethane disulfonic acid, a salt of alcohol sulfuric acid ester, an alkylaryl sulfonate, a lignin sulfonate, a polyoxyethylene glycol ether, a polyoxyethylene alkylaryl ether or a polyoxyethylene sorbitol monoalkylate may, for example, be mentioned.

The adjuvant may, for example, be carboxymethyl cellulose, polyethylene glycol or gum arabic.

In practical use, the herbicide may be diluted to a suitable concentration before application, or may be directly applied.

The herbicide of the present invention may be used for application to foliage, soil or water surface. The blending proportion of the active ingredient is suitably selected as the case requires. However, in a case of a dust or a granule, the proportion of the active ingredient is selected suitably within a range of from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight. In a case of an emulsifiable concentrate or a wettable powder, the proportion is selected suitably within a range of from 1 to 50% by weight, preferably from 5 to 20% by weight.

The dose of the herbicide of the present invention varies depending upon the type of the compound, the weeds to be controlled, the germination tendency, the environmental conditions and the type of the formulation to be used. However, in the case of a dust or a granule which is used by itself, the dose of the active ingredient is selected suitably within a range of from 0.1 g to 5 kg, preferably from 1 g to 1 kg, per 10 ares. In a case of an emulsifiable concentrate or a wettable powder which is used in a liquid state, the dose of the active ingredient is selected suitably within a range of from 1 to 50,000 ppm, preferably from 10 to 10,000 ppm.

Further, the compound of the present invention may be used in combination with an insecticide, a fungicide, other herbicide, a plant growth controlling agent, a fertilizer or the like, as the case requires.

Now, the formulation method will be described with reference to typical Formulation Examples. The compounds, types of the additives and blending ratios are not limited to such specific Examples and may be changed within wide ranges. In the following description, "parts" means "parts by weight".

FORMULATION EXAMPLE 1 (Wettable powder)

To 10 parts by weight of Compound No. 172, 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth and 69 parts of clay were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 2 (Wettable powder)

To 10 parts of Compound No. 2, 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium .beta.-naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth, 5 parts of fine silica and 64 parts of clay were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 3 (Wettable powder)

To 10 parts of Compound No. 24, 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium .beta.-naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth, 5 parts of fine silica and 64 parts of calcium carbonate, were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 4 (Emulsifiable concentrate)

To 10 parts of Compound No. 9, 80 parts of a mixture comprising equal amounts of xylene and isophorone and 10 parts of a mixture comprising a polyoxyethylene sorbitol alkylate surfactant, a polyoxyethylenealkylaryl polymer and an alkylaryl sulfonate, were added, and the mixture was thoroughly stirred to obtain an emulsifiable concentrate.

FORMULATION EXAMPLE 5 (Granule)

1 part of Compound No. 168, 89 parts of a bulking agent comprising a 1:3 mixture of talc and bentonite, 5 parts of fine silica, 5 parts of a mixture comprising a polyoxyethylene sorbitol alkylate surfactant, a polyoxyethylenealkylaryl polymer and an alkylaryl sulfonate and 10 parts of water were mixed and thoroughly kneaded to obtain a paste, which was extruded from sieve apertures with a diameter of 0.7 mm. The extruded product was dried and then cut into a length of from 0.5 to 1 mm to obtain granules.

Now, the herbicidal effects of the compounds of the present invention will be described with reference to Test Examples.

TEST EXAMPLE 1 (Test on herbicidal effects by paddy field soil treatment)

In a plastic pot (surface area: 100 cm.sup.2) filled with paddy field soil, barnyardgrass (Eo), monochoria (Mo) and bulrush (Sc) were sown after puddling and leveling, and flooded to a water depth of 3 cm. Next day, a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied dropwise to the water surface. The dose was 100 g of the active ingredient per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 62-65.

TABLE 60______________________________________ Herbicidal effectsIndex (growth-controlling degree)No. or phytotoxicity______________________________________5 Herbicidal effect or phytotoxicity: at least 90%4 Herbicidal effect or phytotoxicity: at least 70% and less than 90%3 Herbicidal effect or phytotoxicity: at least 50% and less than 70%2 Herbicidal effect or phytotoxicity: at least 30% and less than 50%1 Herbicidal effect or phytotoxicity: at least 10 and less than 30%0 Herbicidal effect or phytotoxicity: 0 to less than 10%______________________________________ TABLE 61______________________________________Structural formulae References______________________________________Comparative compound A ##STR508## Japanese Unexamined Patent Publication No. 121973/1990 Japanese Unexamined Patent Publication No. 56469/1990Comparative compound B ##STR509## Japanese Unexamined Patent Publication No. 121973/1990 Japanese Unexamined Patent Publication No. 56469/1990Comparative compound C ##STR510## Japanese Unexamined Patent Publication No. 121973/1990Comparative compound D ##STR511## Japanese Unexamined Patent Publication No. 121973/1990Comparative compound E ##STR512## Japanese Unexamined Patent Publication No. 121973/1990Comparative compound F ##STR513## Japanese Unexamined Patent Publication No. 121973/1990______________________________________ TABLE 62______________________________________Compound Herbicidal effectNo. Eo Mo Sc______________________________________ 1 5 5 5 2 5 5 5 4 5 5 5 8 5 5 5 9 5 5 510 5 5 511 5 5 512 5 5 513 5 5 516 5 5 524 5 5 526 5 5 534 5 5 535 5 5 536 5 5 538 5 5 540 5 5 542 5 5 545 5 5 548 5 5 550 5 5 559 5 5 561 5 5 562 5 5 563 5 5 571 5 5 588 5 5 5105 5 5 5165 5 5 5167 5 5 5169 5 5 5171 5 5 5172 5 5 5178 5 5 5______________________________________ TABLE 63______________________________________Compound Herbicidal effectNo. Eo Mo Sc______________________________________182 5 5 5262 5 5 5286 5 5 5301 5 5 5365 5 5 5405 5 5 5445 5 5 5505 5 5 5506 5 5 5507 5 5 5508 5 5 5509 5 5 5511 5 5 5512 5 5 5515 5 5 4516 5 5 4519 5 5 5520 5 5 5522 5 5 5523 5 5 5524 5 5 5525 5 5 5526 5 5 5527 5 5 5528 5 5 5529 5 5 5530 5 5 5531 5 5 5533 5 5 5535 5 5 5539 5 5 5541 5 5 5542 5 5 5543 5 5 5______________________________________ TABLE 64______________________________________Compound Herbicidal effectNo. Eo Mo Sc______________________________________534 5 5 5544 5 5 5545 5 5 5546 5 5 5547 5 5 5548 5 5 5549 5 5 5550 5 5 5551 5 5 5553 5 5 5554 5 5 5555 5 5 5556 5 5 5558 5 5 5562 5 5 5563 5 5 5564 5 5 5567 5 5 5568 5 5 5572 5 5 5573 5 5 5575 5 5 5578 5 5 5584 5 5 5588 5 5 5589 5 5 5591 5 5 5593 5 5 5594 5 5 5595 5 5 5596 5 5 5597 5 5 5598 5 5 5599 5 5 5______________________________________ TABLE 65______________________________________Compound Herbicidal effectNo. Eo Mo Sc______________________________________600 5 5 5611 5 5 5613 5 5 5614 5 5 5615 5 5 5616 5 5 5619 5 5 5622 5 5 5626 5 5 5628 5 5 4665 5 5 5671 5 5 5681 5 5 5693 5 5 5770 3 5 5772 5 5 5787 5 5 5789 5 5 5797 5 5 5813 5 5 5815 5 5 5831 5 5 5834 5 3 5929 5 5 5931 5 5 5933 5 5 5952 5 5 5955 5 5 5Comparative 0 0 0compound AComparative 4 1 2compound BComparative 0 0 0compound EComparative 0 0 0compound F______________________________________ TEST EXAMPLE 2 (Test on herbicidal effects by upland field soil treatment)

In a plastic pot.(surface area: 120 cm.sup.2) filled with upland field soil, barnyardgrass (Ec), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and covered with soil. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 l/10 ares so as to apply 100 g of the active ingredient per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 66-69.

TABLE 66______________________________________Compound Herbicidal effectNo. Ec Po Am Ch Ci______________________________________ 2 5 5 5 5 5 4 5 5 5 5 5 8 5 5 5 5 5 9 5 5 5 5 510 5 5 5 5 511 5 5 5 5 512 5 5 5 5 513 5 5 5 5 516 5 5 5 5 524 5 5 5 5 526 5 5 5 5 530 5 5 5 5 534 5 5 5 5 535 5 5 5 5 536 5 5 5 5 538 5 5 5 5 540 5 5 5 5 542 5 5 5 5 548 5 5 5 5 550 5 5 5 5 559 5 5 5 5 561 5 5 5 5 562 5 5 5 5 588 5 5 5 5 5105 5 5 5 5 5109 5 5 5 5 5165 5 5 5 5 5167 5 5 5 5 5169 5 5 5 5 5171 5 5 5 5 5172 5 5 5 5 5178 5 5 5 5 5204 5 5 5 5 5262 5 4 5 5 5______________________________________ TABLE 67______________________________________Compound Herbicidal effectNo. Ec Po Am Ch Ci______________________________________286 5 5 5 5 5301 4 5 5 5 5386 5 5 5 5 5506 5 5 5 5 5507 4 5 5 5 5508 5 5 5 5 5509 4 5 5 5 4511 5 5 5 5 5512 5 5 5 5 5519 5 5 5 5 5520 5 5 5 5 5522 5 5 5 5 5523 5 5 5 5 5524 5 5 5 5 5525 5 5 5 5 5526 5 5 5 5 5528 5 5 5 5 5529 5 5 5 5 5530 5 5 5 5 5531 5 5 5 5 5533 5 5 5 5 5537 4 5 5 5 5539 5 5 5 5 5541 5 5 5 5 5543 5 5 5 5 5544 5 5 5 5 5546 5 5 5 5 5547 5 5 5 5 5548 5 5 5 5 5549 5 5 5 5 5550 5 5 5 5 5551 5 5 5 5 5553 5 5 5 5 5554 5 5 5 5 5______________________________________ TABLE 68______________________________________Compound Herbicidal effectNo. Ec Po Am Ch Ci______________________________________555 5 5 5 5 5556 4 5 5 5 5558 4 5 5 5 5562 5 5 5 5 5563 5 5 5 5 5564 4 5 5 5 5567 4 5 5 5 5568 5 5 5 5 5573 5 5 5 5 5575 5 5 5 5 5578 5 5 5 5 5584 5 5 5 5 5588 5 5 5 5 5589 5 5 5 5 5591 5 5 5 5 5594 5 5 5 5 5595 5 5 5 5 5596 5 5 5 5 5597 5 5 5 5 5598 5 5 5 5 5599 5 5 5 5 5600 4 5 5 5 5611 5 5 5 5 5613 5 5 5 5 5614 5 5 5 5 5615 4 5 5 5 5616 5 5 5 5 5626 5 5 5 5 5627 4 5 5 5 5628 5 5 5 5 5665 5 5 5 5 5667 3 5 5 5 5681 5 5 5 5 5693 3 5 5 5 5______________________________________ TABLE 69______________________________________Compound Herbicidal effectNo. Ec Po Am Ch Ci______________________________________770 3 5 5 5 5772 5 5 5 5 5787 5 5 5 5 5789 5 5 5 5 5797 3 5 5 5 5815 5 5 5 5 5831 3 5 5 5 5834 3 5 5 5 5852 2 5 5 5 5883 3 5 5 3 5929 4 5 4 4 5931 5 5 5 4 5933 5 5 5 5 5952 5 4 5 5 5984 4 5 5 5 5Comparative 0 0 0 0 0compound AComparative 0 0 2 3 0compound BComparative 1 2 5 4 2compound CComparative 0 2 4 4 1compound DComparative 0 0 2 0 1compound EComparative 0 0 0 0 0compound F______________________________________ TEST EXAMPLE 3 (Test on herbicidal effects by upland field foliage treatment)

In a plastic pot (surface area: 120 cm.sup.2) filled with upland field soil, barnyardgrass (Ec), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and covered with soil and were cultured in a green house for 2 weeks. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 l/10 ares so as to apply 100 g of the active ingredient per 10 ares. The plants were then cultured in the green house, and the evaluation of the herbicidal effects was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 70-74.

TABLE 70______________________________________Compound Herbicidal effectNo. Ec Po Am Ch Ci______________________________________ 1 5 5 5 5 5 2 5 5 5 5 5 4 5 5 5 5 5 8 5 5 5 5 5 9 5 5 5 5 510 5 5 5 5 511 5 5 5 5 512 5 5 5 5 513 5 5 5 5 516 5 5 5 5 524 5 5 5 5 526 5 5 5 5 530 5 5 5 5 534 5 5 5 5 535 5 5 5 5 536 5 5 5 5 538 5 5 5 5 540 5 5 5 5 542 5 5 5 5 548 5 5 5 5 559 5 5 5 5 561 5 5 5 5 562 5 5 5 5 571 5 5 5 5 588 5 5 5 5 5105 5 5 5 5 5159 3 5 5 4 5162 5 5 5 5 5165 5 5 5 5 5167 5 5 5 5 5169 5 5 5 5 5171 5 5 5 5 5178 5 5 5 5 5204 5 5 5 5 5______________________________________ TABLE 71______________________________________Compound Herbicidal effectNo. Ec Po Am Ch Ci______________________________________262 5 5 5 5 5286 5 5 5 5 5301 5 5 5 5 3344 3 5 5 5 4365 3 5 5 5 5367 4 5 5 4 5445 5 5 5 5 5488 5 5 5 5 5505 5 5 5 5 4506 5 5 5 5 5507 5 5 5 5 5508 5 5 5 5 5509 5 5 5 5 5511 5 5 5 5 5512 5 5 5 5 5519 5 5 5 5 5520 5 5 5 5 5523 5 5 5 5 5524 5 5 5 5 5525 3 5 5 5 3526 5 5 5 5 5528 5 5 5 5 5529 5 5 5 5 5530 5 5 5 5 5531 5 5 5 5 5533 5 5 5 5 5534 4 5 5 4 5539 5 5 5 5 5540 3 5 5 5 3541 5 5 5 5 5543 5 5 5 5 5544 5 5 5 5 5546 5 5 5 5 5547 5 5 5 5 5______________________________________ TABLE 72______________________________________Compound Herbicidal effectNo. Ec Po Am Ch Ci______________________________________548 5 5 5 5 5549 5 5 5 5 5550 5 5 5 5 5551 5 5 5 5 5553 5 5 5 5 5554 5 5 5 4 5555 5 5 5 3 5556 4 5 5 4 5558 5 5 5 5 5562 5 5 5 5 5563 5 5 5 5 5564 5 5 5 5 5567 5 5 5 5 5568 5 5 5 5 5573 5 5 5 5 5575 5 5 5 5 5578 5 5 5 5 5584 5 5 5 5 5588 5 5 5 5 5589 5 5 5 5 5591 5 5 5 5 5594 5 5 5 5 5595 5 5 5 5 5596 5 5 5 5 5597 5 5 5 5 5598 5 5 5 5 5599 5 5 5 5 5600 5 5 5 5 5611 5 5 5 5 5613 5 5 5 5 5614 5 5 5 5 5615 5 5 5 5 5616 5 5 5 5 5619 4 5 5 5 5______________________________________ TABLE 73______________________________________Compound Herbicidal effectNo. Ec Po Am Ch Ci______________________________________622 4 5 5 5 4627 5 5 5 5 5628 5 5 5 5 4665 5 5 5 5 5667 5 5 5 5 5671 5 5 5 5 5681 5 5 5 5 3691 5 5 5 5 5693 5 5 5 5 5714 5 5 5 5 5738 5 3 5 4 5740 5 5 5 5 5760 3 5 5 4 5770 5 5 5 5 5772 5 5 5 5 5787 5 5 5 5 5789 5 5 5 5 5797 5 5 5 5 5813 5 5 5 5 5815 5 5 5 5 5827 4 5 5 5 3829 5 5 5 5 4831 5 5 5 5 5852 3 5 5 4 3854 5 5 5 3 4885 5 5 5 5 5887 4 5 5 5 5891 5 5 5 5 5892 5 5 5 5 5897 5 5 5 3 5929 5 5 5 5 5931 5 5 5 5 5933 5 5 5 5 5952 5 5 5 5 5______________________________________ TABLE 74______________________________________Compound Herbicidal effectNo. Ec Po Am Ch Ci______________________________________955 5 5 5 5 5683 5 5 5 5 5984 5 5 5 5 5958 5 5 5 5 5Comparative 0 0 0 0 0compound AComparative 0 2 3 3 0compound BComparative 2 1 4 5 2compound CComparative 0 1 2 4 0compound DComparative 0 4 3 0 1compound EComparative 0 0 0 0 0compound F______________________________________ TEST EXAMPLE 4 (Test on crop plant selectivity by paddy field soil treatment)

In a 1/10,000a plastic pot, paddy field soil was filled, irrigated, paddled and leveled. Then, barnyardgrass (Eo), monochoria (Mo) and bulrush (Sc) were sown at a depth of 0.5 cm. Further, two seedlings of rice (Or) of 2.5 leaf stage was transplanted at a transplantation depth of 2 cm. Then, the pot was flooded to a water depth of 3 cm. Next day, a prescribed amount of the active ingredient (g.sup.ai /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied dropwise to the water surface. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 28th day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 75 to 77.

TABLE 75______________________________________ Herbicidal Phyto-Compound Dose effect toxicityNo. (g.sup.ai /10a) Eo Mo Sc Or______________________________________ 1 25 4 4 3 0 2 1.6 5 5 4 0 4 6.3 5 5 3 1 8 6.3 5 5 5 0 9 6.3 5 5 5 0 10 6.3 5 5 5 0 11 6.3 5 5 5 1 12 1.6 5 5 3 0 34 6.3 5 5 5 0 35 6.3 5 5 5 1 36 1.6 5 5 3 0 59 25 5 5 3 0105 25 5 5 3 0165 6.3 5 5 5 0167 25 5 5 5 0169 25 5 5 5 0171 6.3 5 5 5 0172 6.3 5 5 5 0178 25 4 5 5 0262 6.3 4 5 3 0504 25 5 5 3 0509 6.3 5 5 5 0511 1.6 5 5 4 0522 6.3 5 5 5 0523 25 5 5 5 1524 25 5 5 5 0525 6.3 5 5 5 0526 1.6 5 5 4 0528 1.6 5 5 5 0529 1.6 5 5 5 0530 6.3 5 5 5 0531 1.6 5 5 4 1533 6.3 5 5 5 0______________________________________ TABLE 76______________________________________ Herbicidal Phyto-Compound Dose effect toxicityNo. (g.sup.ai /10a) Eo Mo Sc Or______________________________________534 6.3 5 5 5 0541 6.3 5 5 3 0543 6.3 5 5 3 0544 6.3 5 5 5 0545 6.3 3 5 3 0546 6.3 5 5 3 0547 6.3 4 5 4 0548 6.3 4 4 3 0549 6.3 5 5 4 0550 6.3 5 5 3 0551 6.3 5 5 5 0553 6.3 5 5 5 1554 6.3 5 5 5 0555 25 5 5 5 0556 25 5 5 5 0562 6.3 5 5 5 1563 25 5 5 5 0568 25 3 5 5 0572 25 4 5 4 0573 25 5 5 5 0578 25 5 5 5 1600 25 4 5 3 1611 6.3 5 5 3 1613 6.3 5 5 4 0614 6.3 4 5 3 0616 6.3 5 5 5 0623 6.3 4 5 5 0681 25 5 5 4 1797 6.3 4 5 3 0831 6.3 5 5 5 0929 6.3 5 5 5 0931 25 5 5 5 0933 25 4 5 5 1______________________________________ TABLE 77______________________________________ Herbicidal Phyto-Compound Dose effect toxicityNo. (g.sup.ai /10a) Eo Mo Sc Or______________________________________955 25 4 5 5 1Comparative 25 0 0 0 0compound AComparative 25 2 0 0 0compound BComparative 25 3 4 3 4compound CComparative 25 2 3 1 3compound DComparative 100 0 0 0 0compound EComparative 100 0 0 0 0compound F______________________________________ TEST EXAMPLE 5 (Test on crop plant selectivity by upland field soil treatment)

In a plastic pot (surface area: 600 cm.sup.2) filled with upland field soil, wheat (Tr), barnyardgrass (Ec),green foxtail (Se), Johnsongrass (So), Alopecurus myosuroides (Al), pale smartweed (Po), slender amaranth (Am) and common lambsquarters (Ch) were sown and covered with soil. Next day, a prescribed amount of the active ingredient (g.sup.ai /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 l per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 78 to 79.

TABLE 78______________________________________ Herbicidal Phyto-Compound Dose effect toxicityNo. (g.sup.ai /10a) Ec Se So Al Po Am Ch Tr______________________________________ 2 25 5 5 5 5 5 5 5 1 4 25 5 5 5 5 5 5 5 1 9 25 5 5 5 5 5 5 5 1 10 25 5 5 5 5 5 5 5 1 11 25 5 4 5 5 5 5 5 0 12 25 5 5 5 5 5 5 5 1 13 25 4 3 5 5 5 5 5 0 24 25 5 4 5 5 5 5 5 0 26 25 5 4 5 5 5 5 5 0 40 25 4 5 5 3 5 5 5 0 42 25 3 1 4 3 5 5 5 0 61 25 5 5 5 5 5 5 3 0 62 6.3 5 4 5 5 5 5 3 0507 25 5 5 5 5 5 5 5 0511 25 5 3 5 5 5 5 3 0512 6.3 5 3 5 5 5 5 5 0523 25 5 3 4 4 5 5 5 1525 6.3 5 3 5 5 5 5 5 0526 6.3 5 5 5 5 5 5 5 1527 6.3 5 5 5 5 5 5 5 0529 25 5 5 5 5 5 5 5 0531 25 5 5 5 5 5 5 5 0536 6.3 5 3 5 5 5 5 5 0______________________________________ TABLE 79______________________________________ Herbicidal Phyto-Compound Dose effect toxicityNo. (g.sup.ai /10a) Ec Se So Al Po Am Ch Tr______________________________________553 25 5 5 5 5 5 5 5 0554 25 5 5 5 5 5 5 5 0563 6.3 5 4 5 5 5 5 5 0591 6.3 3 4 5 5 5 5 5 0665 6.3 3 3 4 4 5 5 5 0787 6.3 3 5 5 5 5 5 5 3789 6.3 2 3 5 5 5 5 5 2Comparative 25 0 0 0 0 0 0 0 0compound AComparative 25 0 0 0 0 0 1 1 0compound BComparative 100 1 0 1 1 2 5 4 3compound CComparative 400 2 1 3 2 2 5 5 4compound DComparative 25 0 0 0 0 0 0 0 0compound EComparative 25 0 0 0 0 0 0 0 0compound F______________________________________ TEST EXAMPLE 6 (Test on crop plant selectivity by upland field foliage treatment)

In a plastic pot (surface area: 600 cm.sup.2) filled with upland field soil, rice (Or), wheat (Tr), barnyardgrass (Ec), Johnsongrass (So), Alopecurus myosucroides (Al), pale smartweed (Po), slender amaranth (Am) and common lambsquarters (Ch) were sown and cultured in a green house for 2 weeks. Then, a prescribed amount of the active ingredient (g.sup.ai /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 l per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 80 and 81.

TABLE 80______________________________________ Herbicidal Phyto-Compound Dose effect toxicityNo. (g.sup.ai /10a) Ec So Al Po Am Ch Or Tr______________________________________ 2 25 5 5 5 5 5 5 1 1 4 25 5 5 5 5 5 5 0 0 8 25 5 4 5 5 5 5 1 0 9 25 5 5 5 5 5 5 0 0 24 25 5 5 5 5 5 5 2 0 26 25 5 5 5 5 5 5 1 0 34 25 5 5 5 5 5 5 0 0 35 25 5 5 5 5 5 5 0 0 40 25 3 4 3 5 5 4 1 0 42 25 3 3 3 4 4 4 1 0 61 1.6 5 5 5 5 5 3 1 0 62 25 5 5 5 5 5 5 0 0171 25 5 5 5 5 5 5 1 0262 25 5 5 4 4 5 3 0 0506 6.3 5 5 5 5 5 4 1 0507 6.3 5 5 5 5 5 3 1 0509 6.3 5 5 5 5 5 5 1 0511 25 5 5 5 5 5 5 2 0512 25 5 5 5 5 5 5 2 0522 25 5 5 5 5 5 5 2 0526 25 5 5 5 5 5 5 1 1527 6.3 5 5 5 5 5 5 1 0528 25 5 5 5 5 5 5 2 0529 6.3 5 5 5 5 5 5 1 0530 6.3 5 5 5 5 5 5 2 1531 1.6 5 5 5 5 5 5 1 0543 25 5 4 5 5 5 4 1 0547 6.3 5 5 5 5 5 4 2 0548 6.3 5 5 5 4 5 4 2 1549 6.3 5 5 5 5 5 5 0 0550 6.3 5 5 5 5 5 5 0 0551 6.3 5 5 5 5 5 5 2 0562 6.3 5 5 5 5 5 5 0 0______________________________________ TABLE 81______________________________________ Herbicidal Phyto-Compound Dose effect toxicityNo. (gai/10a) Ec So Al Po Am Ch Or Tr______________________________________563 25 5 5 5 5 5 5 0 0567 25 5 5 5 5 5 4 1 0568 25 5 5 5 5 5 5 0 0578 6.3 5 5 5 5 5 4 1 1597 1.6 4 3 5 5 5 5 1 1848 25 2 3 5 5 5 5 1 0929 25 5 5 5 5 5 5 1 0Comparative 25 0 0 0 0 0 0 0 0compound AComparative 25 0 0 0 1 2 1 1 0compound BComparative 100 2 2 1 1 4 5 4 2compound CComparative 400 0 0 0 5 4 5 3 3compound DComparative 100 0 0 0 0 0 0 0 0compound EComparative 100 0 0 0 0 0 0 0 0compound F______________________________________

Claims

1. A pyrimidine of the formula (I): ##STR514## wherein A is a heterocyclic ring of the formula: ##STR515## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy)ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C.sub.1 -C.sub.2 -alkylthio group; a benzylthio group; a phenylthio group; a C.sub.3 -alkenyloxy group which may be substituted with Br, a C.sub.3 -alkynyloxy group; a C.sub.3 -alkenylthio group; a C.sub.3 -alkynylthio group; a C.sub.3 -alkylideneaminoxy group; O.sup.- �N(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.4).sub.4 !.sup.+ ; O.sup.- (CH.sub.3).sub.2 CHNH.sub.3.sup.+ ;O.sup.- CH.sub.3 CH.sub.2 CH.sub.2 NH.sub.3.sup.+ ; O--Na.sup.+ ; or a group of the formula --NR.sup.6 R.sup.7, wherein:

each of R.sup.6 and R.sup.7, which may be the same or different, is a hydrogen atom, a C.sub.1 -C.sub.4 -alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R.sup.6 and R.sup.7 may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring;

each of R.sup.1 and R.sup.2, which may be the same or different, is a hydrogen atom; a formyl group; a C.sub.1 -C.sub.8 -alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR.sup.6 R.sup.7 ; a C.sub.1 -C.sub.8 alkylthiocarbonyl group which may be substituted with diethylamino; a C.sub.3 -C.sub.8 -cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C.sub.1 -C.sub.8 -alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methylthio; a C.sub.3 -cycloalkyl group; a C.sub.1 -C.sub.8 alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; a C.sub.2 -C.sub.3 alkenyl group which may be substituted with CN or nitro; a C.sub.3 alkynyl group; an ethoxy group; a methoxy group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C.sub.3 -C.sub.8 cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C.sub.3 -C.sub.6 alkenyloxycarbonyl group which may be substituted with chlorine; a C.sub.3 -C.sub.6 alkynyloxycarbonyl group; a C.sub.3 -C.sub.6 alkenylthiocarbonyl group; a C.sub.3 -C.sub.6 alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; a halogenated carbonyl group; a group of the formula CR.sup.8 .dbd.N--R.sup.9 ; a group of the formula NR.sup.10 R.sup.11 or a group of the formula N.dbd.CR.sup.12 R.sup.13, wherein:

R.sup.6 and R.sup.7 are as defined above;

R.sup.8 is a hydrogen atom, a phenyl group, or a methyl group;

R.sup.9 is a hydroxyl group, a propyl group, a phenyl group, a benzyl group, a benzyloxy group, a methoxy group, a propoxy group, a propenyloxy group, a propynyloxy group; a phenoxy group, a methylamino group, a dimethylamino group, a phenylamino group or a phenylsulfonylamino group which may be substituted with methyl;

each of R.sup.10 and R.sup.11, which may be the same or different, is a hydrogen atom, a methyl group, a phenyl group, a benzyl group, a formyl group, an acetyl group, a benzoyl group, a pyridylcarbonyl group, an ethoxycarbonyl group, a methylsulfonyl group, a phenylsulfonyl group, a carbamoyl group, an ethylthiocarbonyl group or a phenylthiocarbonyl group which may be substituted with chlorine, or R.sup.10 and R.sup.11 may, together with the nitrogen atom, form a morpholine ring; and

each of R.sup.12 and R.sup.13, which may be the same or different, is a hydrogen atom, a methyl group or a phenyl group, or R.sup.12 and R.sup.13 may, together with the carbon atom to which they are bound, form a cyclopentylidene group;

each of R.sup.3 and R.sup.4, which may be the same or different, is a hydrogen atom; a methoxy group which may be substituted with fluorine; a halogen atom; a methylamino group; a dimethylamino group or a C.sub.1 -C.sub.6 alkyl group;

R.sup.5 is a hydrogen atom; a methyl group which may be substituted with methoxycarbonyl, ethoxycarbonyl, t-butylcarbonyloxy or methoxy; a formyl group; a C.sub.1 -C.sub.8 alkylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group; a carbomoyl group; a C.sub.2 -C.sub.4 alkoxycarbonyl group; a phenyloxycarbonyl group; a benzyloxycarbonyl group; a methylthiocarbonyl group; a phenylthiocarbonyl group; a methylsulfonyl group; a p-tolylsulfonyl group; a tri-C.sub.1 -C.sub.4 -alkylsilyl group; a propenyl group; a propynyl group; a 4,6-dimethoxypyridin-2-yl group or a trichloromethylthio group;

Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group,

n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups,

W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group or a cyanomethylene group, and

Z is a nitrogen atom; or a salt thereof.

2. A pyrimidine of the formula (I): ##STR516## wherein A is a heterocyclic ring of the formula: ##STR517## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy)ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C.sub.1 -C.sub.2 -alkylthio group; a benzylthio group; a phenylthio group; a C.sub.3 -alkenyloxy group which may be substituted with Br, a C.sub.3 -alkynyloxy group; a C.sub.3 -alkenylthio group; a C.sub.3 -alkynylthio group; a C.sub.3 -alkylideneaminoxy group; O.sub.- �N(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.4).sub.4 !.sup.+ ; O.sup.- (CH.sub.3).sub.2 CHNH.sub.3.sup.+ ; O.sup.- CH.sub.3 CH.sub.2 CH.sub.2 NH.sub.3.sup.+ ; O--Na.sup.+ ; or a group of the formula --NR.sup.6 R.sup.7, wherein:

each of R.sup.6 and R.sup.7, which may be the same or different, is a hydrogen atom, a C.sub.1 -C.sub.4 -alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R.sup.6 and R.sup.7 may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring;

each of R.sup.1 and R.sup.2, which may be the same or different, is a hydrogen atom; a formyl group; a C.sub.1 -C.sub.8 -alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR.sup.6 R.sup.7 ; a C.sub.1 -C.sub.8 alkylthiocarbonyl group which may be substituted with diethylamino; a C.sub.3 -C.sub.8 -cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C.sub.1 -C.sub.8 -alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methylthio; a C.sub.3 -cycloalkyl group; a C.sub.1 -C.sub.8 alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; a C.sub.2 -C.sub.3 alkenyl group which may be substituted with CN or nitro; a C.sub.3 alkynyl group; an ethoxy group; a methoxy group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C.sub.3 -C.sub.8 cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C.sub.3 -C.sub.6 alkenyloxycarbonyl group which may be substituted with chlorine; a C.sub.3 -C.sub.6 alkynyloxycarbonyl group; a C.sub.3 -C.sub.6 alkenylthiocarbonyl group; a C.sub.3 -C.sub.6 alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; a halogenated carbonyl group; a group of the formula CR.sup.8 .dbd.N--R.sup.9 ; a group of the formula NR.sup.10 R.sup.11 or a group of the formula N.dbd.CR.sup.12 R.sup.13, wherein:

R.sup.6 and R.sup.7 are as defined above;

R.sup.8 is a hydrogen atom, a phenyl group, or a methyl group;

R.sup.9 is a hydroxyl group, a propyl group, a phenyl group, a benzyl group, a benzyloxy group, a methoxy group, a propoxy group, a propenyloxy group, a propynyloxy group; a phenoxy group, a methylamino group, a dimethylamino group, a phenylamino group or a phenylsulfonylamino group which may be substituted with methyl;

each of R.sup.10 and R.sup.11, which may be the same or different, is a hydrogen atom, a methyl group, a phenyl group, a benzyl group, a formyl group, an acetyl group, a benzoyl group, a pyridylcarbonyl group, an ethoxycarbonyl group, a methylsulfonyl group, a phenylsulfonyl group, a carbamoyl group, an ethylthiocarbonyl group or a phenylthiocarbonyl group which may be substituted with chlorine, or R.sup.10 and R.sup.11 may, together with the nitrogen atom, form a morpholine ring; and

each of R.sup.12 and R.sup.13, which may be the same or different, is a hydrogen atom, a methyl group or a phenyl group, or R.sup.12 and R.sup.13 may, together with the carbon atom to which they are bound, form a cyclopentylidene group;

provided that when A is of the formula (A-1), either R.sup.1 or R.sup.2 is a formyl group, a C.sub.1 -C.sub.8 -alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carbonyl group; a group of the formula --CONR.sup.6 R.sup.7 wherein R.sup.6 and R.sup.7 are as defined above; a C.sub.1 -C.sub.8 alkylthiocarbonyl group which may be substituted with diethylamino; a C.sub.3 -C.sub.8 -cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C.sub.1 -C.sub.8 -alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methylthio; a C.sub.2 -C.sub.3 alkenyl group which may be substituted with CN or nitro; a C.sub.3 alkynyl group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a phenylthiocarbonyl group; a C.sub.3 -C.sub.6 alkenyloxycarbonyl group which may be substituted with chlorine; a C.sub.3 -C.sub.6 alkynyloxycarbonyl group; a C.sub.3 -C.sub.6 alkenylthiocarbonyl group; a C.sub.3 -C.sub.6 alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; or a halogenated carbonyl group;

each of R.sup.3 and R.sup.4, which may be the same or different, is a hydrogen atom; a methoxy group which may be substituted with fluorine; a halogen atom; a methylamino group; a dimethylamino group or a C.sub.1 -C.sub.6 alkyl group;

R.sup.5 is a hydrogen atom; a methyl group which may be substituted with methoxycarbonyl, ethoxycarbonyl, t-butylcarbonyloxy or methoxy; a formyl group; a C.sub.1 -C.sub.8 alkylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group; a carbomoyl group; a C.sub.2 -C.sub.4 alkoxycarbonyl group; a phenyloxycarbonyl group; a benzyloxycarbonyl group; a methylthiocarbonyl group; a phenylthiocarbonyl group; a methylsulfonyl group; a p-tolylsulfonyl group; a tri-C.sub.1 -C.sub.4 -alkylsilyl group; a propenyl group; a propynyl group; a 4,6-dimethoxypyridin-2-yl group or a trichloromethylthio group;

Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group,

n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups,

W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group or a cyanomethylene group, and

Z is a nitrogen atom; or a salt thereof.

3. A triazine derivative or a salt thereof according to claim 1, wherein A in the formula (I) is (A-1), (A-2), (A-3) or (A-4), W is an oxygen atom or a sulfur atom, and each of R.sup.3 and R.sup.4 is an alkoxy group.

4. An herbicidal composition containing an herbicidally effective amount of the triazine of claim 1 and a carrier therefor.

5. An herbicidal composition containing an herbicidally effective amount of the triazine of claim 2 and a carrier therefor.

6. An herbicidal composition containing an herbicidally effective amount of the triazine of claim 3 and a carrier therefor.