TREA

Herbicidal acetals and ketals

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  • Patent Grant
  • 4861366
  • Patent Number
    4,861,366
  • Date Filed
    Thursday, March 31, 1988
    36 years ago
  • Date Issued
    Tuesday, August 29, 1989
    35 years ago
Information
Abstract
Novel furan- and thiophenesulfonamides such as 3-(1,3-dioxolan-2-yl)-N-[(4-methoxy-6-methyl-1,3-5-triazin-2-yl)aminocarbonyl]-2-thiophenesulfonamide and N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1, 3-dioxolan-2-yl)-2-thiophenesulfonamide are highly active pre-emergent and/or post-emergent herbicides.
Description

BACKGROUND OF THE INVENTION
The present invention relates to a novel class of furan- and thiophenesulfonamide compounds and their use as pre-emergent and post-emergent herbicides and as plant growth regulants.
U.S. Pat. Nos. 4,169,719 and 4,127,405 disclose herbicidal benzene-, furan- and thiophenesulfonamides of general formula ##STR1## where R.sub.1 may be an optionally substituted benzene or a furan or thiophene substituted with H, Cl, Br or CH.sub.3.
U.S. Pat. No. 4,398,939 discloses herbicidal thiophenesulfonamides of formula ##STR2## where R is C.sub.1 -C.sub.4 alkyl, C.sub.3 alkenyl, OCH.sub.3, NO.sub.2, Cl, Br, SO.sub.2 NR.sub.1 R.sub.2 or SO.sub.2 N(OCH.sub.3)CH.sub.3.
European patent application (EP-A) No. 30,142, published 6/10/81 discloses herbicidal furan- and thiophenesulfonamides of formula ##STR3## where W' is O or S;
A is C(O)QR.sup.I or C(.dbd.T)R.sup.II ; and
A' is H, Cl, Br, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, NO.sub.2 or CF.sub.3.
U.S. Pat. No. 4,370,480 teaches herbicidal benzenesulfonamides of general formula ##STR4## where R.sub.1 is ##STR5##
EP-A-64,804, published 11/17/82, teaches herbicidal furan- and thiophenesulfonamides of general formula ##STR6## where R.sub.1 is S(O).sub.n R.sub.6 ; and
R.sub.2 is H, Cl, Br or CH.sub.3 ;
EP-A-13,480 discloses herbicidal pyridine-sulfonamides of formula ##STR7## where R.sub.1 is H, Cl, Br, F, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, NO.sub.2 or CO.sub.2 R.sub.5 ; and
R.sub.2 is H, Cl, Br or CH.sub.3.
EP-A-35,893 discloses herbicidal pyridine-sulfonamides of formula ##STR8## where R.sub.1 is S(O).sub.n R.sub.3 ; and
R.sub.2 is H, Cl, F, Br, CH.sub.3, OCH.sub.3, CF.sub.3, NO.sub.2, CN or NH.sub.2.
EP-A-97,122, published Dec. 28, 1983, discloses herbicidal sulfonamides of formula ##STR9## where X is O, S, NR.sub.4 or CR.sub.5 .dbd.N; and
R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl, halogen, NO.sub.2, CWR.sub.8, SO.sub.2 NR.sub.6 R.sub.7 or COR.sub.9.
EP-A-95,925, published Dec. 7, 1983, and EP-A-87,780, published Sept. 7, 1983, teach herbicidal pyrazole sulfonylureas.
EP-A-95,925 (published Dec. 7, 1983) and EP-A-87,780 (published Sept. 7, 1983) teach herbicidal pyrazole sulfonylureas.
EP-A-126,711 (published 11/28/84; Swiss priority 5/16/83) discloses herbicidal sulfonylureas of the formula ##STR10## wherein X is O, S, --NR.sub.5, ##STR11## --CH.dbd.CH-- or an annelated phenyl ring; Z is O or S;
Q is halogen, C.sub.1 -C.sub.4 alkyl, cyano, etc.;
R.sub.1 is H, halogen, NO.sub.2 or a group ##STR12## R.sub.6 is, inter alia, H or C.sub.1 -C.sub.4 alkyl; and R.sub.2 and R.sub.3 can be, among other things, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy.
SUMMARY OF THE INVENTION
This invention relates to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as preemergent and/or postemergent herbicides or plant growth regulants. ##STR13## wherein Q is ##STR14## R is H or CH.sub.3 ; R.sub.1 is ##STR15## E is CH.sub.2 or a single bond; R.sub.2 is H, C.sub.1 -C.sub.2 alkyl or Cl;
R.sub.3 is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy;
R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl;
R.sub.6 and R.sub.7 are independently H or C.sub.1 -C.sub.2 alkyl;
W is O or S;
W.sub.1 is O or S;
Q.sub.1 and Q.sub.2 are independently O, S or NCH.sub.3 ; A is ##STR16## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3)alkylamino;
Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3)alkylamino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.5 alkylthioalkyl, C(O)R.sub.8, ##STR17## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3;
L.sub.1 and L.sub.2 are independently O or S;
R.sub.8 is H or CH.sub.3 ;
R.sub.9 and R.sub.10 are independently C.sub.1 -C.sub.2 alkyl;
R.sub.11 is C.sub.1 -C.sub.3 alkyl;
R.sub.12 is H, F, Cl, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 alkylsulfonyl, di(C.sub.1 -C.sub.2)alkylsulfamoyl or CO.sub.2 (C.sub.1 -C.sub.2 alkyl);
R.sub.13 is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F or NO.sub.2 ;
R.sub.14 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 haloalkoxy, Cl, Br, F, NO.sub.2, di(C.sub.1 -C.sub.3)alkylsulfamoyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3)alkylamino, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3 or CH.sub.2 CN.
Z is CH or N;
Y.sub.1 is O or CH.sub.2 ;
X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; and
Y.sub.2 is H or CH.sub.3 ;
X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ;
Y.sub.3 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, OCF.sub.2 H, SCF.sub.2 H, CH.sub.3 or C.sub.2 H.sub.5 ;
X.sub.3 is CH.sub.3 or OCH.sub.3 ;
Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; and
X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl;
and their agriculturally suitable salts; provided that
(a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
(b) when Y is cyclopropyl, X is other than Cl, F, Br or I;
(c) when R.sub.3 is C.sub.1 -C.sub.3 alkoxy, then Q.sub.1 and Q.sub.2 are oxygen;
(d) when R.sub.3 is H or C.sub.1 -C.sub.3 alkyl, then Q is Q-1 through Q-9;
(e) when X or Y is OCF.sub.2 H, then Z is CH;
(f) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of the substituents on Q is less than or equal to ten;
(g) when W is S, then A is A-1, R is H, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR18## (h) when A is A-7 and Z is N, then R.sub.3 is C.sub.1 -C.sub.3 alkoxy; (i) when E is CH.sub.2, then R.sub.14 is H, CH.sub.3, OCH.sub.3, Cl or NO.sub.2 and is not in the 4-position.
In the above definitions, the term "alkyl" used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.
Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy isomers.
Alkenyl denotes straight chain or branched alkenes, e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.
Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl isomers.
Cycloalkyl denotes cyclopropyl, cyclobutyl and cyclopentyl.
The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine.
In terms such as C.sub.2 -C.sub.5 alkoxyalkoxy, the specified number of carbon atoms is meant to define the total number of carbon atoms in that substituent group. For example, C.sub.2 -C.sub.5 alkoxyalkoxy would represent OCH.sub.2 OCH.sub.3 through O(CH.sub.2).sub.4 OCH.sub.3 or OCH.sub.2 O(CH.sub.2).sub.3 CH.sub.3 and the various structural isomers embraced therein.
Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl and the different propylsulfonyl isomers.
Alkylthio, alkylsulfinyl, alkylamino, alkylsulfamoyl, etc., are defined in an analogous manner.
PREFERRED COMPOUNDS
Preferred for reasons of their higher herbicidal efficacy, greater plant growth regulant activity and/or more favorable ease of synthesis are:
(1) Compounds of Formula I where
R.sub.3 is H or C.sub.1 -C.sub.3 alkyl;
(2) Compounds of Formula I where
R.sub.3 is C.sub.1 -C.sub.3 alkoxy;
(3) Compounds of Preferred 1 where
W is O;
R is H;
X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3 or CF.sub.3 ; and
Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, ##STR19## OCF.sub.2 H, C.tbd.CH, C.tbd.CCH.sub.3, SCF.sub.2 H or cyclopropyl;
(4) Compounds of Preferred 3 where
Q.sub.1 and Q.sub.2 are identical and are O or S;
R.sub.12 is H, C.sub.1 -C.sub.2 alkyl or Cl;
R.sub.13 is H; and
(5) Compounds of Preferred 4 where
A is A-1;
Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, NHCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, OCF.sub.2 H, OCH.sub.2 CH.sub.2 OCH.sub.3, cyclopropyl, C.tbd.CH or CH(OCH.sub.3).sub.2 ; and
X is CH.sub.3, OCH.sub.3, Cl, OC.sub.2 H.sub.5, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ;
(6) Compounds of Preferred 5 where Q.sub.1 and Q.sub.2 are O;
(7) Compounds of Preferred 5 where Q.sub.1 and Q.sub.2 are S;
(8) Compounds of Preferred 5 where Q is Q-1;
(9) Compounds of Preferred 5 where Q is Q-2;
(10) Compounds of Preferred 5 where Q is Q-3;
(11) Compounds of Preferred 5 where Q is Q-4;
(12) Compounds of Preferred 5 where Q is Q-5;
(13) Compounds of Preferred 5 where Q is Q-6;
(14) Compounds of Preferred 5 where Q is Q-7;
(15) Compounds of Preferred 5 where Q is Q-8;
(16) Compounds of Preferred 5 where Q is Q-9;
(17) Compounds of Preferred 2 where
W is O;
R is H;
X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3 or CF.sub.3 ; and
Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, ##STR20## OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ;
(18) Compounds of Preferred 17 where
E is a single bond;
R.sub.12 is H, C.sub.1 -C.sub.2 alkyl or Cl;
R.sub.13 is H; and
R.sub.14 is H, F, Cl, Br, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio and is not para to the sulfonylurea bridge;
(19) Compounds of Preferred 18 where
A is A-1;
Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, NHCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, OCF.sub.2 H, OCH.sub.2 CH.sub.2 OCH.sub.3, cyclopropyl, C.tbd.CH or CH(OCH.sub.3).sub.2 ; and
X is CH.sub.3, OCH.sub.3, Cl, OC.sub.2 H.sub.5, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ;
(20) Compounds of Preferred 19 where Q is Q-1;
(21) Compounds of Preferred 19 where Q is Q-2;
(22) Compounds of Preferred 19 where Q is Q-3;
(23) Compounds of Preferred 19 where Q is Q-4;
(24) Compounds of Preferred 19 where Q is Q-5;
(25) Compounds of Preferred 19 where Q is Q-6;
(26) Compounds of Preferred 19 where Q is Q-7;
(27) Compounds of Preferred 19 where Q is Q-8;
(28) Compounds of Preferred 19 where Q is Q-9;
(29) Compounds of Preferred 19 where Q is Q-10;
Specifically Preferred for reasons of highest herbicidal efficacy and/or most favorable ease of synthesis are:
3-(1,3-dioxolan-2-yl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophenesulfonamide, m.p. 164.degree.-166.degree. C.; and
N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1,3-dioxolan-2-yl)-2-thiophenesulfonamide, m.p. 137.degree.-150.degree. C.
DETAILED DESCRIPTION OF THE INVENTION
Synthesis
The compounds of Formula I can be prepared by one or more of the methods shown in Equations 1-7.
As shown in Equation 1, compounds of Formula I (where W is O) can be prepared by treating sulfonamides of Formula II with phenyl esters of N-heterocycliccarbamic acids of Formula III in the presence of a strong organic base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). ##STR21## wherein Q, R and A are as previously defined. The reaction of Equation 1 is generally carried out in the range of 0.degree. to 50.degree. C. in an inert solvent such as dioxane or acetonitrile, analogous to methods taught in EP-A 44,807. The required carbamates can be prepared from the corresponding amines, IIIa, and diphenyl carbonate or phenylchloroformate and a base such as sodium hydride as shown in Equation 2. ##STR22##
Compounds of Formula I may also be prepared as shown in Equation 3 by treating sulfonamides of Formula II with the methyl ester of an N-heterocycliccarbamic acid of Formula IIIb in the presence of an equimolar quantity of trimethylaluminum. ##STR23##
The reaction of Equation 3 is best carried out at temperatures between 25.degree. and 83.degree. C. in a solvent such as methylene chloride or 1,2-dichloroethane for 12 to 95 hours under an inert atmosphere, as taught in EP-A 84,244, published July 27, 1983. The methyl carbamates, IIIb, can be conveniently synthesized by treatment of the corresponding heterocyclic amines of Formula IIIa with dimethyl carbonate or methyl chloroformate in the presence of a base such as sodium hydride.
Alternatively, compounds of Formula I can be prepared by the reaction of a sulfonylcarbamate of Formula IV with an aminoheterocycle of Formula IIIa as shown in Equation 4. ##STR24##
The reaction is carried out at 50.degree. to 100.degree. C. in a solvent such as dioxane for 0.5 to 24 hours as taught in EP-A-44,807. The required carbamates of Formula IV are prepared by the reaction of the corresponding sulfonamides of Formula II with diphenylcarbonate or phenylchloroformate in the presence of a base such as sodium hydride.
Compounds of Formula I, where W is S, can be prepared via addition of an appropriate heterocyclic amine, IIIa, to a sulfonyl isothiocyanate of the formula QSO.sub.2 NCS. This reaction is best carried out according to methods taught in U.S. Pat. No. 4,127,405.
Sulfonyl isothiocyanates of the formula QSO.sub.2 NCS can be prepared according to the procedure of K. Hartke, Arch. Pharm., 299, 174 (1966).
Sulfonamides of Formula II used in the preparation of compounds of Formula I are useful intermediates. They can be prepared by a variety of methods known in the art. For example, contacting an appropriately substituted sulfonyl chloride IIa with ammonium hydroxide or ammonia in an inert solvent such as ether or tetrahydrofuran affords sulfonamides II as shown by Equation 5a and 5b. ##STR25##
The reaction of sulfonyl chlorides, IIa, with ammonia is best carried out at -33.degree. to 50.degree. C. for 0.1 to 24 hours. After removal of the ammonium chloride by-product by filtration or extraction with water, the desired product can be isolated by the evaporation of the organic solvent.
Ammonium hydroxide can be used in place of ammonia as in Equation 5b. This reaction is widely reported in the literature, c.f., Methoden Der Organischen Chemie (Houben-Weyl), Vol. 9, Ch. 19, edited by F. Muth, Stuttgart, 1955.
Alternatively, sulfonamides of Formula II can be prepared by the reaction of a lithium salt of an appropriately substituted sulfinic acid, IIb, with chloramine as shown in Equation 6. ##STR26##
This reaction can be carried out using the conditions referred to in the preceding reference.
Lithium salts of Formula IIb can also be converted to the sulfonamides of Formula IIa by the procedures taught in U.S. Pat. No. 4,441,910.
Sulfonyl chlorides of Formula IIa can be prepared by the reaction of lithium salts of Formula IIc with sulfuryl chloride at -50.degree. to -20.degree. C. in an inert solvent such as tetrahydrofuran or ether as shown in Equation 7.
______________________________________Equation 7______________________________________(a) QH + R'Li .fwdarw. QLi IIc(b) QBr + R'Li .fwdarw. IIc(c) IIc + SO.sub.2 Cl.sub.2 .fwdarw. IIa______________________________________
Where R' is a group such as butyl, phenyl, diisopropylamino or similar moiety commonly combined with lithium to form a lithiation agent. These agents and their method of use are described in N. S. Narasimhan and R. S. Mali, Synthesis, 957-86 (1983) or in The Chemistry of Organolithium Compounds, Wakefield, Pergamon Press, Oxford, 1974 or also H. W. Gschwend and H. R. Rodriguez, Org. React. 26, 1 (1978).
The sulfonyl chlorides, IIa, can be isolated by extracting the inorganic by-products with water followed by drying the organic layer over a drying agent such as magnesium sulfate, filtering the dried solution and evaporation of the solvent.
Lithium salts of Formula IIb can be prepared by contacting sulfur dioxide with the lithiated intermediate IIc using procedures described in the above references on the lithiated intermediates.
The formation of orthoesters, acetals, cyclic acetals, thioacetals and their amino analogs where Q.sub.1 or Q.sub.2 are N--CH.sub.3 is widely reported in the literature, c.f.: Synthetic Organic Chemistry, R. B. Wagner and H. D. Zook, Ch. 8, John Wiley & Sons, New York, 1953; or Organic Synthesis, V. Migrdichian, Ch. 5, Reinhold, London, 1957.
The desired aldehyde and acetyl substituted thiophenes can be prepared by a variety of methods as described, for example, in "The Chemistry of Heterocyclic Compounds", vol. 3, edited by H. D. Hartough, F. P. Hochgesang and F. F. Blicke, Interscience, N.Y., 1952. Pyrazole aldehydes and acetylpyrazoles can be prepared according procedures described in "The Chemistry of Heterocyclic Compounds", Vol. 22, edited by R. H. Wiley, Interscience, N.Y., 1967. Aldehydes and acetyl derivatives of furan can be prepared according to methods cited in "Advances in Heterocyclic Chemistry", Vol. 7, edited by A. R. Katritzky and A. J. Boulton, and Vol. 30 edited by A. R. Katritzky, Academic Press, N.Y., 1962 and 1982. Further references to the literature of heterocyclic compounds can be found on pages 225-299 of Vol. 7 cited above.
The heterocyclic amines of Formula IIIa can be prepared by methods known in the literature, or simple modifications thereof, by those skilled in the art. For instance, EP-A No. 84,224 (published July 27, 1983) and W. Braker et al., J. Am. Chem. Soc., 69, 3072 (1947) describes methods for preparing aminopyrimidines and triazines substituted by acetal groups such as dialkoxymethyl or 1,3-dioxolan-2-yl, among other groups. Also, for example, South African patent application Nos. 82/5045 and 82/5671 describe methods for preparing aminopyrimidines and triazines substituted by haloalkyl or haloalkylthio groups such as OCH.sub.2 CH.sub.2 F, OCH.sub.2 CF.sub.3, SCF.sub.2 H, or OCF.sub.2 H, among other groups. South African patent application 83/7434 (published Oct. 5, 1983) describes methods for the synthesis of cyclopropylpyrimidines and triazines substituted by such groups as alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino or alkoxyalkyl.
The 5,6-dihydrofuro[2.3-d]pyrimidin-2-amines, the cylcopenta[d.pi.pyrimidin-2-amines (IIIa, A is A-2) and the 6,7-dihydro-5H-pyrano[2.3-d]pyrimidin-2-amines (IIIa, A is A-3) can be prepared as described in EP-A No. 15,683. The furo[2.3-d]pyrimidin-2-amines (III, A is A-4) are described in EP-A No. 46,677.
Compounds of Formula IIIa, where A is A-5, are described in EP-A-73,562. Compounds of Formula IIIa, where A is A-6, are described in EP-A-94,260. Compounds of Formula IIIa, where A is A-7, can be prepared by methods taught in EP-A-125,864.
In addition, general methods for preparing aminopyrimidines and triazines have been reviewed in the following publications:
"The Chemistry of Heterocyclic Compounds," a series published by Interscience Publ., New York and London;
"Pyrimidines", Vol. 16 of the same series by D. J. Brown;
"s-Triazines and Derivatives," Vol. 13 of the same series by E. M. Smolin and L. Rapaport;
F. C. Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812 (1963), which describes the synthesis of triazines.
Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known in the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide or carbonate). Quaternary amine salts can be made by similar techniques.
Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.
Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble.
Acid addition salts, useful in this invention, can be obtained by reacting a compound for Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.





The preparation of the compounds of this invention is further illustrated by the following specific examples. Unless otherwise indicated, temperatures are given in degrees centrigrade.
EXAMPLE 1
3-(1,3-Dioxolan-2-yl)thiophene-2-sulfonyl chloride
To 23.4 g of 3-(1,3-dioxolan-2-yl)thiophene (S. Gronowitz, et al., Arkiv. Kemi., 20, 407 (1963)) in 100 ml of anhydrous tetrahydrofuran was added 100 ml of 1.6 molar n-butyllithium in hexane, with ice bath cooling. After stirring at room temperature for 20 minutes the mixture was cooled to -78.degree. and sulfuryl chloride (16.2 g) was then added dropwise. This addition caused the suspended solids to form a tarry mass which broke up when the mixture was allowed to warm to room temperasture. After stirring one and one half hours at room temperature the mixture was cooled to -10.degree. and 10 ml of ethyl acetate was added dropwise. The reaction mixture was then poured into ice water and extracted with ethyl ether. The ether portions were combined, dried over magnesium sulfate, filtered and the ether removed in vacuo-to yield 19.6 g of an oil. Infrared absorption spectra of this product showed peaks at 1330 and 1180 cm.sup.-1, consistent for the desired sulfonyl chloride. Mass spectrum analysis: calc. 254, found 253 (Mass-1H) and the presence of a chlorine atom.
EXAMPLE 2
3-(1,3-Dioxolan-2-yl)thiophene-2-sulfonamide
To 5 ml of liquified ammonia gas dissolved in 50 ml of tetrahydrofuran was added dropwise with stirring and cooling 12.7 g of 3-(1,3-dioxolan-2-yl)thiophene-2-sulfonyl chloride. After stirring overnight at ambient temperature, the tetrahydrofuran was removed in vacuo, water was added to the residue and the mixture was extracted twice with 75 ml of methylene chloride. After washing the combined methylene chloride extracts with water, drying over magnesium sulfate, filtering off the drying agent and evaporation of the methylene chloride, an oily solid residue was obtained. This was chromatographed through silica gel using 1:1 ethyl acetate-hexanes as eluant (Rf 0.35). Evaporation of the solvent mixture yielded 2.2 g of the desired product, as a waxy solid. Infrared absorption spectra showed peaks at 3360, 3260, 1340 and 1140 cm.sup.-1, consistent for a primary sulfonamide. Mass spectrum analysis: calc. 235, found 234 (Mass-1H).
EXAMPLE 3
3-(1,3-Dioxolan-2-yl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophenesulfonamide
To 0.47 g of 3-(1,3-dioxolan-2-yl)thiophene-2-sulfonamide in 20 ml of acetonitrile was added 0.52 g of phenyl(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate and 0.3 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After stirring at ambient temperatures for two hours the solution was diluted to 50 ml with water and the pH was adjusted to 3 by the addition of hydrochloride acid. The resultant solution was extracted with methylene chloride and the methylene chloride phase was dried over magnesium sulfate, filtered and evaporated. Trituration of the residue with butyl chloride yielded 0.6 g of the product, m.p. 164.degree.-166.degree.. Infrared absorption spectra showed peaks at 1700, 1600 and 1550 cm.sup.-1, consistent for the desired structure. ##STR27##
EXAMPLE 4
N-[4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1,3-dioxolan-2-yl)-2-thiophenesulfonamide
To 0.47 g of 3-(1,3-dioxolan-2-yl)thiophene-2-sulfonamide in 20 ml of acetonitrile was added 0.5 g of phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate and 0.3 ml of DBU. After stirring for two hours at ambient temperature, 25 ml of water was added to the mixture and the solution was acidified to pH 3 with 10% hydrochloric acid. The precipitated product was removed by filtration, washed with water and air dried to yield 0.9 g of the subject compound, m.p. 157-168. Infrared absorption peaks at 1700, 1600, 1570 cm.sup.-1 were consistent for the desired structure.
______________________________________NMR(CDCl.sub.3): .delta. 3.95 (m. CH.sub.2 O); 3.95 (s. CH.sub.3 O); 5.77 (s. pyrimidine); 6.44 (s. dioxolane); 7.25 (d. thiophene); 7.57 (d. thiophene).______________________________________
By using the procedures described in the foregoing equations and examples or modifications thereof, one skilled in the art can prepare the compounds shown in the following tables. ##STR28##
TABLE I__________________________________________________________________________GENERAL STRUCTURE IR.sub.1 R.sub.2 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dixolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCF.sub.2 H CH.sub.3 CH1,3-dioxolan-2-yl H H O CF.sub.2 H OCH.sub.3 CH1,3-dioxolan-2-yl H H O CF.sub.2 H OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F CH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CHF.sub.2 CH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H H O CF.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O CF.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 N(CH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.3 N(CH.sub.3)OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.2 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 SCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 C.tbd.CH N1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 SCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 SCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH(OCH.sub.3).sub.2 CH1,3-dioxolan-2-yl H H O CH.sub.3 i-C.sub.3 H.sub.7 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH(OCH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxolan- CH 2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxolan-2 N 2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 4-methyl-1,3- N dioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 4-methyl-1,3- CH dioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 4-ethyl-1,3- CH dioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxan-2-yl N1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxan-2-yl CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl CH1,3-dioxolan-2-yl H H O OCF.sub.2 H OCF.sub.2 H CH1,3-dioxolan-2-yl H H O Br OCF.sub.2 H CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O F CH.sub.3 CH1,3-dioxolan-2-yl H H O F OCH.sub.3 CH1,3-dioxolan-2-yl H H O Br OCH.sub.3 CH1,3-dioxolan-2-yl H H O Br CH.sub.3 CH1,3-dioxolan-2-yl H H O I OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl CH1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.3 CH(SCH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.3 CH(SCH.sub.3).sub.2 CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dithiolan- CH 2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dithiolan- N 2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-oxathiolan- N 2-yl1,3-dioxolan-2-yl H CH.sub.3 O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H CH.sub.3 O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H CH.sub.3 O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H H S CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H S OCH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H H S OCH.sub.3 OCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N--CH(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--CH(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 N--CH(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N 147-165--CH(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CH--CH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH 156-158--CH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N 135-139--CH(OCH.sub.3).sub.2 H H O Cl OCH.sub.3 CH 151-154--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 N--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N 120-126--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CH 141-144--C(CH.sub.3)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH 148-152--C(CH.sub.3)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N--C(CH.sub.3)(OCH.sub.3).sub.2 H H O Cl OCH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 CH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 CH.sub.3 N--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 OCH.sub.3 N--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 OCH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 N--CH(SCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--CH(SCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 N--CH(SCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--CH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--CH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 Ndioxolan-2-yl2-methyl-1,3- H H O Cl OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O Br OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O OC.sub.2 H.sub.5 NHCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O Cl OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O Br OCH.sub.3 CHdioxolan-2-yl1,3-oxathiolan-2-yl H H O OC.sub.2 H.sub.5 NHCH.sub.3 N1,3-oxathiolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-oxathiolan-2-yl H H O CH.sub.3 CH.sub.3 N1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 N1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 CH1,3-oxathiolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-oxathiolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-oxathiolan-2-yl H H O Cl OCH.sub.3 CH1,3-oxathiolan-2-yl H H O OC.sub.2 H.sub.5 NHCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 CH.sub.3 CHdithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 CH.sub.3 Ndithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdithiolan-2-yl2-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdithiolan-2-ylhexahydro-1,3-dimethyl- H H O OCH.sub.3 OCH.sub.3 Npyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 CH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 CH.sub.3 Npyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 Npyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O OCH.sub.3 OCH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O OCH.sub.3 OCH.sub.3 Npyrimidin-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub. 3 CHdioxolan-2-yl4,5-dimethyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl1,3-dimethyl-2- H H O OCH.sub.3 OCH.sub.3 Nimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 CH.sub.3 CHimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 CH.sub.3 Nimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 Nimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 CHimidazolinyl1,3-dimethyl-2- H H O OCH.sub.3 OCH.sub.3 CHimidazolinyl1,3-dioxolan-2-yl 5-CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl 5-CH.sub.3 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl 5-CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl 4-CH.sub.3 H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl 4-CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl 4-CH.sub.3 H O CH.sub.3 CH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub. 3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O Br OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 H CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 H CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O OCF.sub.2 H OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 CH(OCH.sub.3).sub.2 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OC.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 C.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O Cl OC.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCF.sub.2 H CH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CF.sub.2 H OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CF.sub.2 H OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 cyclo- N propyl--C(OCH.sub.3).sub.3 H H O OCF.sub.2 H OCF.sub.2 H CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 N--C(OC.sub.2 H.sub.5)(OCH.sub.3).sub.2) H H O OCH.sub.3 OCH.sub.3 CH2-methoxy-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Br OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 H CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 H CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCF.sub.2 H OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 CH(OCH.sub.3).sub.2 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OC.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 C.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Cl OC.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCF.sub.2 H CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CF.sub.2 H OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CF.sub.2 H OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 cyclo- N propyl--C(OC.sub.2 H.sub.5).sub.3 H H O OCF.sub.2 H OCF.sub.2 H CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.3 N--C(OCH.sub.3)(OCH.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 CH2-ethoxy-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CH--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N--C(n-C.sub.3 H.sub.7)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH2-ethyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-y12-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl2-propyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-propyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-propyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 C.tbd.CH CH1,3-dioxolan-2-yl H H O OCH.sub.3 CF.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 SCF.sub.2 H CH1,3-dioxolan-2-yl H H O CH.sub.2 F OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 H CH1,3-dioxolan-2-yl H H O CH.sub.3 OC.sub.2 H.sub.5 CHC(OCH.sub.3).sub.3 H H O F OCH.sub.3 CHC(OCH.sub.3).sub.3 H H O I OCH.sub.3 CHC(OCH.sub.3).sub.3 H H O OCH.sub.3 C.tbd.CH CH__________________________________________________________________________
TABLE Ia__________________________________________________________________________GENERAL STRUCTURE IaR.sub.1 R.sub.12 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCF.sub.2 H CH.sub.3 CH1,3-dioxolan-2-yl H H O CF.sub.2 H OCH.sub.3 CH1,3-dioxolan-2-yl H H O CF.sub.2 H OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F CH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CHF.sub.2 CH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H H O CF.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O CF.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 N(CH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.3 N(CH.sub.3)OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.2 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 SCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 C.tbd.CH N1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 SCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 SCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH(OCH.sub.3).sub.2 CH1,3-dioxolan-2-yl H H O CH.sub.3 i-C.sub.3 H.sub.7 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH(OCH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxolan-2-yl CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxolan-2-yl N1,3-dioxolan-2-yl H H O OCH.sub.3 4-methyl-1,3- N dioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 4-methyl-1,3- CH dioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 4-ethyl-1,3- CH dioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxan-2-yl N1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxan-2-yl CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl CH1,3-dioxolan-2-yl H H O OCF.sub.2 H OCF.sub.2 H CH1,3-dioxolan-2-yl H H O Br OCF.sub.2 H CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O F CH.sub.3 CH1,3-dioxolan-2-yl H H O F OCH.sub.3 CH1,3-dioxolan-2-yl H H O Br OCH.sub.3 CH1,3-dioxolan-2-yl H H O Br CH.sub.3 CH1,3-dioxolan-2-yl H H O I OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl CH1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.3 CH(SCH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.3 CH(SCH.sub.3).sub.2 CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dithiolan-2-yl CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dithiolan-2-yl N1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-oxathiolan-2-yl N1,3-dioxolan-2-yl H CH.sub.3 O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H CH.sub.3 O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H CH.sub.3 O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H H S CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H S OCH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H H S OCH.sub.3 OCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N--CH(OCH.sub. 3).sub.2 H H O CH.sub.3 CH.sub.3 CH--CH(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 N--CH(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--CH(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CH--CH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--CH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N--CH(OCH.sub.3).sub.2 H H O Cl OCH.sub.3 CH--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 N--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CH--C(CH.sub.3)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--C(CH.sub.3)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N--C(CH.sub.3)(OCH.sub.3).sub.2 H H O Cl OCH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 CH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 CH.sub.3 N--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 OCH.sub.3 N--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 OCH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 N--CH(SCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--CH(SCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 N--CH(SCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--CH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--CH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 Ndioxolan-2-yl2-methyl-1,3- H H O Cl OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O Br OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O OC.sub.2 H.sub.5 NHCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O Cl OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O Br OCH.sub.3 CHdioxolan-2-yl1,3-oxathiolan-2-yl H H O OC.sub.2 H.sub.5 NHCH.sub.3 N1,3-oxathiolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-oxathiolan-2-yl H H O CH.sub.3 CH.sub.3 N1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 N1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 CH1,3-oxathiolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-oxathiolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-oxathiolan-2-yl H H O Cl OCH.sub.3 CH1,3-oxathiolan-2-yl H H O OC.sub.2 H.sub.5 NHCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 CH.sub.3 CHdithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 CH.sub.3 Ndithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdithiolan-2-yl2-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdithiolan-2-ylhexahydro-1,3-dimethyl- H H O OCH.sub.3 OCH.sub.3 Npyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 CH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 CH.sub.3 Npyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 Npyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O OCH.sub.3 OCH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O OCH.sub.3 OCH.sub.3 Npyrimidin-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4,5-dimethyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl1,3-dimethyl-2- H H O OCH.sub.3 OCH.sub.3 Nimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 CH.sub.3 CHimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 CH.sub.3 Nimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 Nimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 CHimidazolinyl1,3-dimethyl-2- H H O OCH.sub.3 OCH.sub.3 CHimidazolinyl1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O Br OCH.sub. 3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 H CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 H CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O OCF.sub.2 H OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 CH(OCH.sub.3).sub.2 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OC.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 C.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O Cl OC.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCF.sub.2 H CH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CF.sub.2 H OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CF.sub.2 H OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 cyclo- N propyl--C(OCH.sub.3).sub.3 H H O OCF.sub.2 H OCF.sub.2 H CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Br OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 H CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 H CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5 ).sub.3 H H O OCF.sub.2 H OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 CH(OCH.sub.3).sub.2 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OC.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 C.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Cl OC.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCF.sub.2 H CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CF.sub.2 H OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CF.sub.2 H OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 cyclo- N propyl--C(OC.sub.2 H.sub.5).sub.3 H H O OCF.sub.2 H OCF.sub.2 H CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CH--C(C.sub.2 H.sub.5)(OCH.sub. 3).sub.2 H H O CH.sub.3 CH.sub.3 CH--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N--C(n-C.sub.3 H.sub.7)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH2-ethyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl2-propyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-propyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-propyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl1,3-dioxolan-2-yl C.sub.2 H.sub.5 H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl Cl H O OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE Ib__________________________________________________________________________GENERAL STRUCTURE IbR.sub.1 R.sub.12 R W X Y Z m.p. .degree. C.__________________________________________________________________________1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCF.sub.2 H CH.sub.3 CH1,3-dioxolan-2-yl H H O CF.sub.2 H OCH.sub.3 CH1,3-dioxolan-2-yl H H O CF.sub.2 H OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F CH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CHF.sub.2 CH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H H O CF.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O CF.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 N(CH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.3 N(CH.sub.3)OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.2 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 SCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 C.tbd.CH N1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 SCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 SCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH(OCH.sub.3).sub.2 CH1,3-dioxolan-2-yl H H O CH.sub.3 i-C.sub.3 H.sub.7 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH(OCH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxolan-2-yl CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxolan-2-yl N1,3-dioxolan-2-yl H H O OCH.sub.3 4-methyl-1,3- N dioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 4-methyl-1,3- CH dioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 4-ethyl-1,3- CH dioxolan-2-yl1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxol-2-yl N1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxol-2-yl CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl CH1,3-dioxolan-2-yl H H O OCF.sub.2 H OCF.sub.2 H CH1,3-dioxolan-2-yl H H O Br OCF.sub.2 H CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O F CH.sub.3 CH1,3-dioxolan-2-yl H H O F OCH.sub.3 CHl,3-dioxolan-2-yl H H O Br OCH.sub.3 CH1,3-dioxolan-2-yl H H O Br CH.sub.3 CH1,3-dioxolan-2-yl H H O I OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl CH1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.3 CH(SCH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.3 CH(SCH.sub.3).sub.2 CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dithiolan-2-yl CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dithiolan-2-yl N1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-oxathiolan-2-yl N1,3-dioxolan-2-yl H CH.sub.3 O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H CH.sub.3 O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H CH.sub.3 O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H H S CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H S OCH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl H H S OCH.sub.3 OCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N--CH(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--CH(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 N--CH(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--CH(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CH--CH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--CH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N--CH(OCH.sub.3).sub.2 H H O Cl OCH.sub.3 CH--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 N--C(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--C(CH.sub.3)(OCH.sub. 3).sub.2 H H O CH.sub.3 OCH.sub.3 CH--C(CH.sub.3)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--C(CH.sub.3)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N--C(CH.sub.3)(OCH.sub.3).sub.2 H H O Cl OCH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 CH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 CH.sub.3 N--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 OCH.sub.3 N--CH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 OCH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--CH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 N--CH(SCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--CH(SCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 N--CH(SCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--CH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--CH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 Ndioxolan-2-yl2-methyl-1,3- H H O Cl OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O Br OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O OC.sub.2 H.sub.5 NHCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O Cl OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O Br OCH.sub.3 CHdioxolan-2-yl1,3-oxathiolan-2-yl H H O OC.sub.2 H.sub.5 NHCH.sub.3 N1,3-oxathiolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-oxathiolan-2-yl H H O CH.sub.3 CH.sub.3 N1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 N1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 CH1,3-oxathiolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-oxathiolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-oxathiolan-2-yl H H O Cl OCH.sub.3 CH1,3-oxathiolan-2-yl H H O OC.sub.2 H.sub.5 NHCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 CH.sub.3 CHdithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 CH.sub.3 Ndithiolan-2-yl 32-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdithiolan-2-yl2-methyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdithiolan-2-ylhexahydro-1,3-dimethyl- H H O OCH.sub.3 OCH.sub.3 Npyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 CH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 CH.sub.3 Npyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 Npyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O OCH.sub.3 OCH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O OCH.sub.3 OCH.sub.3 Npyrimidin-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 CH.sub.3 Ndixolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4,5-dimethyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 CH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 CH.sub.3 Ndioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl1,3-dimethyl-2- H H O OCH.sub.3 OCH.sub.3 Nimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 CH.sub.3 CHimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 CH.sub.3 Nimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 Nimidazolinyl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 CHimidazolinyl1,3-dimethyl-2- H H O OCH.sub.3 OCH.sub.3 CHimidazolinyl1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O Br OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 H CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 H CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O OCF.sub.2 H OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 CH(OCH.sub.3).sub.2 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OC.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.3 C.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O Cl OC.sub.2 H.sub.5 CH--C(OCH.sub.3).sub.3 H H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCF.sub.2 H CH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CF.sub.2 H OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CF.sub.2 H OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 cyclo- N propyl--C(OCH.sub.3).sub.3 H H O OCF.sub.2 H OCF.sub.2 H CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Br OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 H CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 H CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCF.sub.2 H OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 CH(OCH.sub.3).sub.2 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OC.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 C.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Cl OC.sub.2 H.sub.5 CH--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCF.sub.2 H CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CF.sub.2 H OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CF.sub.2 H OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 cyclo- N propyl--C(OC.sub.2 H.sub.5).sub.3 H H O OCF.sub.2 H OCF.sub.2 H CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.3 N-- C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CH--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N--C( -n-C.sub.3 H.sub.7)(OCH.sub.3).sub.2 H H O OCH.sub. 3 OCH.sub.3 CH2-ethyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl2-propyl-1,3- H H O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-propyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-propyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl__________________________________________________________________________
TABLE Ic__________________________________________________________________________GENERAL STRUCTURE IcR.sub.1 R.sub.12 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O OCF.sub.2 H OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O OCH.sub.2 CHF.sub.2 OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 N(CH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O CF.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O I OCH.sub.3 CH1,3-dioxolan-2-yl H H O Br OCH.sub.3 CH1,3-dioxolan-2-yl H H O F OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 SCH.sub.3 CH1,3-dioxolan-2-yl H H O OCF.sub.2 H OCF.sub.2 H CH1,3-dioxolan-2-yl H H O OCH.sub.3 NHCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 N(OCH.sub.3)CH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 C.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.3 SCF.sub.2 H CH1,3-dioxolan-2-yl H H O OCH.sub.3 CH(OCH.sub.3).sub.2 CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxolan-2-yl CH1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 C.tbd.CH N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 CH1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl 4-CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl 4-C.sub.2 H.sub.5 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl 4-Cl H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H S CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dithiolan-2-yl H H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CHCH(OCH.sub.3).sub.2 H H O Cl OCH.sub.3 CHCH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 NCH(OCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 NCH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 CH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 CH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O Cl OCH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 NCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 CH.sub.3 NCH(SCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CHCH(SCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 CHCH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CHCH(SCH.sub.3).sub.2 H H O Cl OCH.sub.3 CHCH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 NCH(SCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 NC(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CHC(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 NC(CH.sub.3)(SCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CHC(CH.sub.3)(SCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 CH1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndithiolan-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 Npyrimidin-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 CHimidazolidinyl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 Nimidazolidinyl--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE Id__________________________________________________________________________GENERAL STRUCTURE IdR.sub.1 R.sub.12 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O OCF.sub.2 H OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O OCH.sub.2 CHF.sub.2 OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 N(CH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O CF.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O I OCH.sub.3 CH1,3-dioxolan-2-yl H H O Br OCH.sub.3 CH1,3-dioxolan-2-yl H H O F OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 SCH.sub.3 CH1,3-dioxolan-2-yl H H O OCF.sub.2 H OCF.sub.2 H CH1,3-dioxolan-2-yl H H O OCH.sub.3 NHCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 N(OCH.sub.3)CH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 C.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.3 SCF.sub.2 H CH1,3-dioxolan-2-yl H H O OCH.sub.3 CH(OCH.sub.3).sub.2 CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxolan-2-yl CH1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 C.tbd.CH N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 CH1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl C.sub.2 H.sub.5 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl Cl H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H S CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dithiolan-2-yl H H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CHCH(OCH.sub.3).sub.2 H H O Cl OCH.sub.3 CHCH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 NCH(OCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 NCH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 CH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 CH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O Cl OCH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 NCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 CH.sub.3 NCH(SCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CHCH(SCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 CHCH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CHCH(SCH.sub.3).sub.2 H H O Cl OCH.sub.3 CHCH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 NCH(SCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 NC(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CHC(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 i-C.sub.3 H.sub.7 CHC(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 NC(CH.sub.3)(SCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CHC(CH.sub.3)(SCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O CH.sub. 3 OCH.sub.3 Ndioxolan-2-yl1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 CH1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndithiolan-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.2 OCH.sub.3 Npyrimidin-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 CHimidazolidinyl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 Nimidazolidinyl--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE Ie__________________________________________________________________________GENERAL STRUCTURE IeR.sub.1 R.sub.12 R W K Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O OCF.sub.2 H OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CH.sub.2 F OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O OCH.sub.2 CHF.sub.2 OCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 N(CH.sub.3).sub.2 N1,3-dioxolan-2-yl H H O OCH.sub.2 CF.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H H O CF.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H H O I OCH.sub.3 CH1,3-dioxolan-2-yl H H O Br OCH.sub.3 CH1,3-dioxolan-2-yl H H O F OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O CH.sub.3 CH.sub.2 SCH.sub.3 CH1,3-dioxolan-2-yl H H O OCF.sub.2 H OCF.sub.2 H CH1,3-dioxolan-2-yl H H O OCH.sub.3 NHCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 N(OCH.sub.3)CH.sub.3 N1,3-dioxolan-2-yl H H O OCH.sub.3 C.sub.2 H.sub.5 N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H H O OCH.sub.3 cyclopropyl N1,3-dioxolan-2-yl H H O OCH.sub.3 SCF.sub.2 H CH1,3-dioxolan-2-yl H H O OCH.sub.3 CH(OCH.sub.3).sub.2 CH1,3-dioxolan-2-yl H H O OCH.sub.3 1,3-dioxolan-2-yl CH1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 .tbd.CH N1,3-dioxolan-2-yl H H O CH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 CH1,3-dioxolan-2-yl H H O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dioxolan-2-yl C.sub.2 H.sub.5 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl Cl H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H CH.sub.3 O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H H S CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 CH1,3-dithiolan-2-yl H H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl H H O OCH.sub.3 OCH.sub.3 N1,3-dithiolan-2-yl H H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CHCH(OCH.sub.3).sub.2 H H O Cl OCH.sub.3 CHCH(OCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 NCH(OCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 NCH(OC.sub.2 H.sub.5).sub.2 H H O CH.sub.3 CH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 CH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O Cl OCH.sub.3 CHCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 OCH.sub.3 NCH(OC.sub.2 H.sub.5).sub.2 H H O OCH.sub.3 CH.sub.3 NCH(SCH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CHCH(SCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 CHCH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CHCH(SCH.sub.3).sub.2 H H O Cl OCH.sub.3 CHCH(SCH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 NCH(SCH.sub.3).sub.2 H H O OCH.sub.3 CH.sub.3 NC(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CHC(CH.sub.3)(OCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 NC(CH.sub.3)(SCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CHC(CH.sub.3)(SCH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N2-methyl-1.3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 CH1,3-oxathiolan-2-yl H H O CH.sub.3 OCH.sub.3 N2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdithiolan-2-yl2-methyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndithiolan-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 CHpyrimidin-2-ylhexahydro-1,3-dimethyl- H H O CH.sub.3 OCH.sub.3 Npyrimidin-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4,5-dimethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 CHdioxolan-2-yl4-ethyl-1,3- H H O CH.sub.3 OCH.sub.3 Ndioxolan-2-yl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 CHimidazolidinyl1,3-dimethyl-2- H H O CH.sub.3 OCH.sub.3 Nimidazolidinyl--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 H H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 CH-- C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.T).sub.3 H H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H H O OCH.sub.3 OCH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.2 H H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.2 H H O Cl OCH.sub.3 CH--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.2 H H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.2 H H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE II__________________________________________________________________________General structure IIR.sub.1 R.sub.11 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 cyclo- CH propyl1,3-dioxolan-2-yl C.sub.3 H.sub.7 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 CH.sub.3 O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 CH.sub.3 H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.t).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE IIa__________________________________________________________________________General structure IlaR.sub.1 R.sub.11 R W X Y Z m.P. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 cyclo- CH propyl1,3-dioxolan-2-yl C.sub.3 H.sub.7 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 CH.sub.3 O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 CH.sub.3 H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub. H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1.3-dithiolan-2-yl CH.sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 CH--C(OC.sub.2 H.sub.5 ).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE IIb__________________________________________________________________________General Structure IIbR.sub.1 R.sub.11 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 cyclo- CH propyl1,3-dioxolan-2-yl C.sub.3 H.sub.7 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 CH.sub.3 O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 CH.sub.3 H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 CH.sub. 3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE IIc__________________________________________________________________________General Structure IIcR.sub.1 R.sub.11 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H O OCH.sub.3 cyclo- CH propyl1,3-dioxolan-2-yl C.sub.3 H.sub.7 H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 CH.sub.3 O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 CH.sub.3 H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 CH.sub.3 H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl CH.sub.3 H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl CH.sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 CH.sub. 3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 CH.sub.3 H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE III__________________________________________________________________________General Structure IIIR.sub.1 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.2 CH.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H O OCH.sub.3 cyclo- CH propyl1,3-dioxolan-2-yl H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE IIIa__________________________________________________________________________General Structure IIIaR.sub.1 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dioxolsn-2-yl H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H O OCH.sub.3 cyclo- CH propyl1,3-dioxolan-2-yl H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE IIIb__________________________________________________________________________General structure IIIbR.sub.1 R W X Y Z m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H O CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H O CH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H O OCH.sub.3 OCH.sub.3 CH1,3-dioxolan-2-yl H O Cl OCH.sub.3 CH1,3-dioxolan-2-yl H O CH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.3 OCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.2 CH.sub.2 F NHCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.2 CF.sub.3 NHCH.sub.3 N1,3-dioxolan-2-yl H O OCH.sub.3 CH.sub.2 OCH.sub.3 CH1,3-dioxolan-2-yl H O OCH.sub.3 cyclo- CH propyl1,3-dioxolan-2-yl H O OCH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl H S CH.sub.3 CH.sub.3 CH1,3-dioxolan-2-yl CH.sub.3 O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H O OCH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H O OCH.sub.3 CH.sub.3 NCH(OCH.sub.3).sub.2 H O CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H O Cl OCH.sub.3 CH1,3-dithiolan-2-yl H O OCH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H O OCH.sub.3 CH.sub.3 N1,3-dithiolan-2-yl H O CH.sub.3 CH.sub.3 CH1,3-dithiolan-2-yl H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O CH.sub.3 CH.sub.3 CH--C(OCH.sub.3).sub.3 H O Cl OCH.sub.3 CH--C(OCH.sub.3).sub.3 H O CH.sub.3 OCH.sub.3 N--C(OCH.sub.3).sub.3 H O OCH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H O OCH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O CH.sub.3 OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O CH.sub.3 CH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O Cl OCH.sub.3 CH--C(OC.sub.2 H.sub.5).sub.3 H O CH.sub.3 OCH.sub.3 N--C(OC.sub.2 H.sub.5).sub.3 H O OCH.sub.3 OCH.sub.3 N__________________________________________________________________________
TABLE IV__________________________________________________________________________General Structure IVR.sub.1 R.sub.2 R W W.sub.1 A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H H O S A-2 CH.sub.3 O --1,3-dioxolan-2-yl H H O S A-2 OCH.sub.3 O --1,3-dioxolan-2-yl H H O S A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl H H O S A-2 CH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H H O S A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H H O S A-2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dioxolan-2-yl H H O O A-2 CH.sub.3 O --1,3-dioxolan-2-yl H H O O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl H H O O A-2 OCH.sub.3 CH.sub.2 --1,3-dithiolan-2-yl H H O S A-2 CH.sub.3 O --1,3-dithiolan-2-yl H H O S A-2 OCH.sub.3 CH.sub.2 --1,3-dithiolan-2-yl H H O O A-2 CH.sub.3 O --1,3-dithiolan-2-yl H H O O A-2 OCH.sub.3 CH.sub.2 --CH(OCH.sub.3 ).sub.2 H H O S A-2 CH.sub.3 O --CH(OCH.sub.3).sub.2 H H O O A-2 CH.sub.3 O --1,3-dioxolan-2-yl H H O S A-3 CH.sub.3 -- --1,3-dioxolan-2-yl H H O S A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl H H O O A-3 OCF.sub.2 H -- --1,3-dioxolan-2-yl H H O S A-4 OCH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H H O S A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H H O S A-4 OC.sub.2 H.sub.5 -- H1,3-dioxolan-2-yl H H O O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H H O O A-4 OCF.sub.2 H -- CH.sub.31,3-dithiolan-2-yl H H O S A-3 CH.sub.3 -- --1,3-dithiolan-2-yl H H O S A-4 CH.sub.3 -- CH.sub.3CH(OCH.sub.3).sub.2 H H O S A-3 OCH.sub.3 -- --CH(OCH.sub.3).sub.2 H H O S A-4 OCH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H O S A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 H H O S A-2 OCH.sub.3 O --C(OCH.sub.3).sub.3 H H O S A-2 OCF.sub.2 H O --C(OCH.sub.3).sub.3 H H O S A-2 CH.sub.3 CH.sub.2 --C(OCH.sub.3).sub.3 H H O S A-2 OCH.sub.3 CH.sub.2 --C(OCH.sub.3).sub.3 H H O S A-2 OC.sub.2 H.sub.5 CH.sub.2 --C(OCH.sub.3).sub.3 H H O O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 H H O O A-3 OCH.sub.3 -- --C(OCH.sub.3).sub.3 H H O O A-3 OCF.sub.2 H -- --C(OCH.sub.3).sub.3 H H O O A-4 OCH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H O O A-4 CH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H O O A-4 OC.sub.2 H.sub.5 -- HC(OCH.sub.3).sub.3 H H O O A-4 OCF.sub.2 H -- CH.sub.3C(OCH.sub.3).sub.3 H H O O A-2 CH.sub.3 O --C(OC.sub.2 H.sub.5).sub.3 H H O O A-2 CH.sub.3 O --C(OC.sub.2 H.sub.5).sub.3 H H O S A-2 CH.sub.3 O --__________________________________________________________________________ X.sub.2 Y.sub.3__________________________________________________________________________C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 OCH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 OC.sub.2 H.sub.5C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 SCH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 SC.sub.2 H.sub.5C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 CH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 C.sub.2 H.sub.5C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 OCF.sub.2 HC(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 SCF.sub.2 HC(OCH.sub.3).sub.3 H H O S A-5 C.sub.2 H.sub.5 OCH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.2 CF.sub.3 OCH.sub.3C(OCH.sub.3).sub.3 H H O O A-5 CH.sub.3 OCH.sub.3__________________________________________________________________________ X.sub.2 Y.sub. 3 --__________________________________________________________________________1,3-dioxolan- H H O S A-5 CH.sub.3 OCH.sub.3 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 OC.sub.2 H.sub.5 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 SCH.sub.3 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 SC.sub.2 H.sub.5 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 OCF.sub.2 H --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 SCF.sub.2 H --2-ylCH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 OCH.sub.3 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 OC.sub.2 H.sub.5 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 SCH.sub.3 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 SC.sub.2 H.sub.5 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 OCF.sub.2 H --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 SCF.sub.2 H --CH(OCH.sub.3).sub.2 H H O O A-5 CH.sub.3 OCH.sub.3 --__________________________________________________________________________ X.sub.3__________________________________________________________________________C(OCH.sub.3).sub.3 H H O S A-6 CH.sub.3 -- --C(OCH.sub.3).sub.3 H H O S A-6 OCH.sub.3 -- --1,3-dioxolan- H H O S A-6 CH.sub.3 -- --2-yl1,3-dioxolan- H H O S A-6 OCH.sub.3 -- --2-ylCH(OCH.sub.3).sub.2 H H O S A-6 CH.sub.3 -- --CH(OCH.sub.3).sub.2 H H O S A-6 OCH.sub.3 -- --CH(OCH.sub.3).sub.2 H H O O A-6 CH.sub.3 -- --__________________________________________________________________________ X.sub.4 Y.sub.4 Z__________________________________________________________________________CH(OCH.sub.3).sub.2 H H O S A-7 CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H H O S A-7 OCH.sub.3 OCH.sub.3 CH1,3-dioxolan- H H O S A-7 CH.sub.3 CH.sub.3 CH2-yl1,3-dioxolan- H H O S A-7 OCH.sub.3 OCH.sub.3 CH2-ylC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.3 CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 OCH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 Cl CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 Cl CHC(OCH.sub.3).sub.3 H H O S A-7 OC.sub.2 H.sub.5 CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.2 OCH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.2 OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 NC(OCH.sub.3).sub.3 H H O O A-7 CH.sub.3 CH.sub.3 CH__________________________________________________________________________
TABLE IVa__________________________________________________________________________General Structure IVa__________________________________________________________________________R.sub.1 R.sub.12 R W W.sub.1 A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H H O S A-2 CH.sub.3 O --1,3-dioxolan-2-yl H H O S A-2 OCH.sub.3 O --1,3-dioxolan-2-yl H H O S A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl H H O S A-2 CH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H H O S A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H H O S A-2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dioxolan-2-yl H H O O A-2 CH.sub.3 O --1,3-dioxolan-2-yl H H O O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl H H O O A-2 OCH.sub.3 CH.sub.2 --1,3-dithiolan-2-yl H H O S A-2 CH.sub.3 O --1,3-dithiolan-2-yl H H O S A-2 OCH.sub.3 CH --1,3-dithiolan-2-yl H H O O A-2 CH.sub.3 O --1,3-dithiolan-2-yl H H O O A-2 OCH.sub.3 CH --CH(OCH.sub.3).sub.2 H H O S A-2 CH.sub.3 O --CH(OCH.sub.3).sub.2 H H O O A-2 CH.sub.3 O --1,3-dioxolan-2-yl H H O S A-3 CH.sub.3 -- --1,3-dioxolan-2-yl H H O S A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl H H O O A-3 OCF.sub.2 H -- --1,3-dioxolan-2-yl H H O S A-4 OCH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H H O S A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H H O S A-4 OC.sub.2 H.sub.5 -- H1,3-dioxolan-2-yl H H O O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H H O O A-4 OCF.sub.2 H -- CH.sub.31,3-dithiolan-2-yl H H O S A-3 CH.sub.3 -- --1,3-dithiolan-2-yl H H O S A-4 CH.sub.3 -- CH.sub.3CH(OCH.sub.3).sub.2 H H O S A-3 OCH.sub.3 -- --CH(OCH.sub.3).sub.2 H H O S A-4 OCH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H O S A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 H H O S A-2 OCH.sub.3 O --C(OCH.sub.3).sub.3 H H O S A-2 OCF.sub.2 H O --C(OCH.sub.3).sub.3 H H O S A-2 CH.sub.3 CH.sub.2 --C(OCH.sub.3).sub.3 H H O S A-2 OCH.sub.3 CH.sub.2 --C(OCH.sub.3).sub.2 H H O S A-2 OC.sub.2 H.sub.5 CH.sub.2 --C(OCH.sub.3).sub.3 H H O O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 H H O O A-3 OCH.sub.3 -- --C(OCH.sub.3).sub.3 H H O O A-3 OCF.sub.2 H -- --C(OCH.sub.3).sub.3 H H O O A-4 OCH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H O O A-4 CH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H O O A-4 OC.sub.2 H.sub.5 -- HC(OCH.sub.3).sub.3 H H O O A-4 OCF.sub.2 H -- CH.sub.3C(OCH.sub.3).sub.3 H H O O A-2 CH.sub.3 O --C(OC.sub.2 H.sub.5).sub.3 H H O O A-2 CH.sub.3 O --C(OC.sub.2 H.sub.5 ).sub.3 H H O S A-2 CH.sub.3 O -- X.sub.2 Y.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 OCH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 OC.sub.2 H.sub.5C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 SCH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 SC.sub.2 H.sub.5C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 CH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 C.sub.2 H.sub.5C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 OCF.sub.2 HC(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 SCF.sub.2 HC(OCH.sub.3).sub.3 H H O S A-5 C.sub.2 H.sub.5 OCH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.2 CF.sub.3 OCH.sub.3C(OCH.sub.3).sub.3 H H O O A-5 CH.sub.3 OCH.sub.31,3-dioxolan- H H O S A-5 CH.sub.3 OCH.sub.3 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 OC.sub.2 H.sub.5 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 SCH.sub.3 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 SC.sub.2 H.sub.5 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 OCF.sub.2 H --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 SCF.sub.2 H --2-ylCH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 OCH.sub.3 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 OC.sub.2 H.sub.5 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 SCH.sub.3 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 SC.sub.2 H.sub.5 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 OCF.sub.2 H --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 SCF.sub.2 H --CH(OCH.sub.3).sub.2 H H O O A-5 CH.sub.3 OCH.sub.3 -- X.sub.3C(OCH.sub.3).sub.3 H H O S A-6 CH.sub.3 -- --C(OCH.sub.3 ).sub.3 H H O S A-6 OCH.sub.3 -- --1,3-dioxolan- H H O S A-6 CH.sub.3 -- --2-yl1,3-dioxolan- H H O S A-6 OCH.sub.3 -- --2-ylCH(OCH.sub.3).sub.2 H H O S A-6 CH.sub.3 -- --CH(OCH.sub.3).sub.2 H H O S A-6 OCH.sub.3 -- --CH(OCH.sub.3).sub.2 H H O O A-6 CH.sub.3 -- -- X.sub.4 Y.sub.4 ZCH(OCH.sub.3).sub.2 H H O S A-7 CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H H O S A-7 OCH.sub.3 OCH.sub.3 CH1,3-dioxolan- H H O S A-7 CH.sub.3 CH.sub.3 CH2-yl1,3-dioxolan- H H O S A-7 OCH.sub.3 OCH.sub.3 CH2-ylC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.3 CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 OCH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 Cl CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 Cl CHC(OCH.sub.3).sub.3 H H O S A-7 OC.sub.2 H.sub.5 CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.2 OCH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.2 OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 NC(OCH.sub.3).sub.3 H H O O A-7 CH.sub.3 CH.sub.3 CH__________________________________________________________________________
TABLE IVb__________________________________________________________________________General Structure IVb__________________________________________________________________________R.sub.1 R.sub.12 R W W.sub.1 A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl H H O S A-2 CH.sub.3 O --1,3-dioxolan-2-yl H H O S A-2 OCH.sub.3 O --1,3-dioxolan-2-yl H H O S A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl H H O S A-2 CH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H H O S A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H H O S A-2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dioxolan-2-yl H H O O A-2 CH.sub.3 O --1,3-dioxolan-2-yl H H O O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl H H O O A-2 OCH.sub.3 CH.sub.2 --1,3-dithiolan-2-yl H H O S A-2 CH.sub.3 O --1,3-dithiolan-2-yl H H O S A-2 OCH.sub.3 CH --1,3-dithiolan-2-yl H H O O A-2 CH.sub.3 O --1,3-dithiolan-2-yl H H O O A-2 OCH.sub.3 CH --CH(OCH.sub.3).sub.2 H H O S A-2 CH.sub.3 O --CH(OCH.sub.3).sub.2 H H O O A-2 CH.sub.3 O --1,3-dioxolan-2-yl H H O S A-3 CH.sub.3 -- --1,3-dioxolan-2-yl H H O S A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl H H O O A-3 OCF.sub.2 H -- --1,3-dioxolan-2-yl H H O S A-4 OCH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H H O S A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H H O S A-4 OC.sub.2 H.sub.5 -- H1,3-dioxolan-2-yl H H O O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H H O O A-4 OCF.sub.2 H -- CH.sub.31,3-dithiolan-2-yl H H O S A-3 CH.sub.3 -- --1,3-dithiolan-2-yl H H O S A-4 CH.sub.3 -- CH.sub.3CH(OCH.sub.3).sub.2 H H O S A-3 OCH.sub.3 -- --CH(OCH.sub.3).sub.2 H H O S A-4 OCH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H O S A-2 CH.sub. 3 O --C(OCH.sub.3).sub.3 H H O S A-2 OCH.sub.3 O --C(OCH.sub.3).sub.3 H H O S A-2 OCF.sub.2 H O --C(OCH.sub.3).sub.3 H H O S A-2 CH.sub.3 CH.sub.2 --C(OCH.sub.3).sub.3 H H O S A-2 OCH.sub.3 CH.sub.2 --C(OCH.sub.3).sub.3 H H O S A-2 OC.sub.2 H.sub.5 CH.sub.2 --C(OCH.sub.3).sub.3 H H O O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 H H O O A-3 OCH.sub.3 -- --C(OCH.sub.3).sub.3 H H O O A-3 OCF.sub.2 H -- --C(OCH.sub.3).sub.3 H H O O A-4 OCH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H O O A-4 CH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H O O A-4 OC.sub.2 H.sub.5 -- HC(OCH.sub.3).sub.3 H H O O A-4 OCF.sub.2 H -- CH.sub.3C(OCH.sub.3).sub. 3 H H O O A-2 CH.sub.3 O --C(OC.sub.2 H.sub.5).sub.3 H H O O A-2 CH.sub.3 O --C(OC.sub.2 H.sub.5).sub.3 H H O S A-2 CH.sub.3 O -- X.sub.2 Y.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 OCH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 OC.sub.2 H.sub.5C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 SCH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 SC.sub.2 H.sub.5C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 CH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 C.sub.2 H.sub.5C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 OCF.sub.2 HC(OCH.sub.3).sub.3 H H O S A-5 CH.sub.3 SCF.sub.2 HC(OCH.sub.3).sub.3 H H O S A-5 C.sub.2 H.sub.5 OCH.sub.3C(OCH.sub.3).sub.3 H H O S A-5 CH.sub.2 CF.sub.3 OCH.sub. 3C(OCH.sub.3).sub.3 H H O O A-5 CH.sub.3 OCH.sub.31,3-dioxolan- H H O S A-5 CH.sub.3 OCH.sub.3 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 OC.sub.2 H.sub.5 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 SCH.sub.3 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 SC.sub.2 H.sub.5 --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 OCF.sub.2 H --2-yl1,3-dioxolan- H H O S A-5 CH.sub.3 SCF.sub.2 H --2-ylCH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 OCH.sub.3 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 OC.sub.2 H.sub.5 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 SCH.sub.3 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 SC.sub.2 H.sub.5 --CH(OCH.sub.3).sub.2 H H O S A-5 CH.sub.3 OCF.sub.2 H --CH(OCH.sub.3).sub. 2 H H O S A-5 CH.sub.3 SCF.sub.2 H --CH(OCH.sub.3).sub.2 H H O O A-5 CH.sub.3 OCH.sub.3 -- X.sub.3C(OCH.sub.3).sub.3 H H O S A-6 CH.sub.3 -- --C(OCH.sub.3).sub.3 H H O S A-6 OCH.sub.3 -- --1,3-dioxolan- H H O S A-6 CH.sub.3 -- --2-yl1,3-dioxolan- H H O S A-6 OCH.sub.3 -- --2-ylCH(OCH.sub.3).sub.2 H H O S A-6 CH.sub.3 -- --CH(OCH.sub.3).sub.2 H H O S A-6 OCH.sub.3 -- --CH(OCH.sub.3).sub.2 H H O O A-6 CH.sub.3 -- -- X.sub.4 Y.sub.4 ZCH(OCH.sub.3).sub.2 H H O S A-7 CH.sub.3 CH.sub.3 CHCH(OCH.sub.3).sub.2 H H O S A-7 OCH.sub.3 OCH.sub.3 CH1,3-dioxolan- H H O S A-7 CH.sub.3 CH.sub.3 CH2-yl1,3-dioxolan- H H O S A-7 OCH.sub.3 OCH.sub.3 CH2-ylC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.3 CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 OCH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 Cl CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 OCH.sub.3 Cl CHC(OCH.sub.3).sub.3 H H O S A-7 OC.sub.2 H.sub.5 CH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.2 OCH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H O S A-7 CH.sub.2 OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H O S A-7 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 NC(OCH.sub.3).sub.3 H H O O A-7 CH.sub.3 CH.sub.3 CH__________________________________________________________________________
TABLE V__________________________________________________________________________General Structure V__________________________________________________________________________R.sub.1 R.sub.11 R W A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl CH.sub.3 H O A-2 CH.sub.3 O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 CH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dithiolan-2-yl CH.sub.3 H O A-2 CH.sub.3 O --1,3-dithiolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-3 CH.sub.3 -- --1,3-dioxolan-2-yl CH.sub.3 H O A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl CH.sub.3 H O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl CH.sub.3 H O A-4 OCH.sub.3 -- H1,3-dioxolan-2-yl CH.sub.3 H O A-4 OCF.sub.2 H -- CH.sub.3__________________________________________________________________________R.sub.1 R.sub.11 R.sub.12 R W A.sub.1 X.sub.1 Y.sub.2 Y m.p. .degree.C.__________________________________________________________________________C(OCH.sub.3).sub.3 CH.sub.3 H H O A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 CH.sub.3 H H O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 H H O A-4 CH.sub.3 -- CH.sub.3__________________________________________________________________________ X.sub.2 Y.sub.2__________________________________________________________________________C(OCH.sub.3).sub.3 CH.sub.3 H H O A-5 CH.sub.3 -- OCH.sub.31,3-dioxolan- CH.sub.3 H H O A-5 CH.sub.3 SCH.sub.3 --2-yl__________________________________________________________________________ X.sub.3__________________________________________________________________________C(CH.sub.3)(OCH.sub.3).sub.2 CH.sub.3 H H O A-6 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 H H O A-6 OCH.sub.3 -- --__________________________________________________________________________ X.sub.4 Y.sub.4 Z__________________________________________________________________________1,3-dioxolan- CH.sub.3 H H O A-7 CH.sub.3 CH.sub.3 CH2-ylC(OCH.sub.3).sub.3 CH.sub.3 H H O A-7 OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE va__________________________________________________________________________General Structure VaR.sub.1 R.sub.11 R W A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl CH.sub.3 H O A-2 CH.sub.3 O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 CH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dithiolan-2-yl CH.sub.3 H O A-2 CH.sub.3 O --1,3-dithiolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-3 CH.sub.3 -- --1,3-dioxolan-2-yl CH.sub.3 H O A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl CH.sub.3 H O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl CH.sub.3 H O A-4 OCH.sub.3 -- H1,3-dioxolan-2-yl CH.sub.3 H O A-4 OCF.sub.2 H -- CH.sub.3C(OCH.sub.3).sub.3 CH.sub.3 H O A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 CH.sub.3 H O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 H O A-4 CH.sub.3 -- CH.sub.3__________________________________________________________________________ X.sub.2 Y.sub.2__________________________________________________________________________C(OCH.sub.3).sub.3 CH.sub.3 H O A-5 CH.sub.3 OCH.sub.31,3-dioxolan- CH.sub.3 H O A-5 CH.sub.3 SCH.sub.32-yl__________________________________________________________________________ X.sub.3__________________________________________________________________________C(CH.sub.3)(OCH.sub.3).sub.2 CH.sub.3 H O A-6 CH.sub.3C(OCH.sub.3).sub.3 CH.sub.3 H O A-6 OCH.sub.3__________________________________________________________________________ X.sub.4 Y.sub.4 Z__________________________________________________________________________1,3-dioxolan- CH.sub.3 H O A-7 CH.sub.3 CH.sub.3 CH2-ylC(OCH.sub.3).sub.3 CH.sub.3 H O A-7 OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE Vb__________________________________________________________________________ General Structure Vb__________________________________________________________________________R.sub.1 R.sub.11 R W A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl CH.sub.3 H O A-2 CH.sub.3 O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 CH.sub.3 CH.sub.31,3-dioxolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dithiolan-2-yl CH.sub.3 H O A-2 CH.sub.3 O --1,3-dithiolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-3 CH.sub.3 -- --1,3-dioxolan-2-yl CH.sub.3 H O A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl CH.sub.3 H O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl CH.sub.3 H O A-4 OCH.sub.3 -- H1,3-dioxolan-2-yl CH.sub.3 H O A-4 OCF.sub.2 H CH.sub.3C(OCH.sub.3).sub.3 CH.sub.3 H O A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 CH.sub.3 H O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 H O A-4 CH.sub.3 -- CH.sub.3__________________________________________________________________________ X.sub.2 Y.sub.3__________________________________________________________________________C(OCH.sub.3).sub.3 CH.sub.3 H O A-5 CH.sub.3 OCH.sub.31,3-dioxolan- CH.sub.3 H O A-5 CH.sub.3 SCH.sub.32-yl__________________________________________________________________________ X.sub.3__________________________________________________________________________C(CH.sub.3)(OCH.sub.3).sub.2 CH.sub.3 H O A-6 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 H O A-6 OCH.sub.3 -- --__________________________________________________________________________ X.sub.4 Y.sub.4 Z__________________________________________________________________________1,3-dioxolan- CH.sub.3 H O A-7 CH.sub.3 CH.sub.3 CH2-ylC(OCH.sub.3).sub.3 CH.sub.3 H O A-7 OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE Vc__________________________________________________________________________ General Structure Vc__________________________________________________________________________R.sub.1 R.sub.11 R W A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree.C.__________________________________________________________________________1,3-dioxolan-2-yl CH.sub.3 H O A-2 CH.sub.3 O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl CH.sub.3 H O A-2 CH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dithiolan-2-yl CH.sub.3 H O A-2 CH.sub.3 O --1,3-dithiolan-2-yl CH.sub.3 H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl CH.sub.3 H O A-3 CH.sub.3 -- --1,3-dioxolan-2-yl CH.sub.3 H O A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl CH.sub.3 H O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl CH.sub.3 H O A-4 OCH.sub.3 -- H1,3-dioxolan-2-yl CH.sub.3 H O A-4 OCF.sub.2 H -- CH.sub.3C(OCH.sub.3 ).sub.3 CH.sub.3 H O A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 CH.sub.3 H O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 H O A-4 CH.sub.3 -- CH.sub.3__________________________________________________________________________ X.sub.2 Y.sub.3__________________________________________________________________________C(OCH.sub.3).sub.3 CH.sub.3 H O A-5 CH.sub.3 OCH.sub.31,3-dioxolan- CH.sub.3 H O A-5 CH.sub.3 SCH.sub.32-yl__________________________________________________________________________ X.sub.3__________________________________________________________________________C(CH.sub.3)(OCH.sub.3).sub.2 CH.sub.3 H O A-6 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 H O A-6 OCH.sub.3 -- --__________________________________________________________________________ X.sub.4 Y.sub.4 Z__________________________________________________________________________1,3-dioxolan- CH.sub.3 H O A-7 CH.sub.3 CH.sub.3 CH2-ylC(OCH.sub.3).sub.3 CH.sub.3 H O A-7 OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE VI__________________________________________________________________________ General Structure VI__________________________________________________________________________R.sub.1 R W A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree. C.__________________________________________________________________________1,3-dioxolan-2-yl H O A-2 CH.sub.3 O --1,3-dioxolan-2-yl H O A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl H O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl H O A-2 CH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H O A-2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dithiolan-2-yl H O A-2 CH.sub.3 O --1,3-dithiolan-2-yl H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H O A-3 CH.sub.3 -- --1,3-dioxolan-2-yl H O A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl H O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H O A-4 OCH.sub.3 -- H1,3-dioxolan-2-yl H O A-4 OCF.sub.2 H -- CH.sub.3C(OCH.sub.3).sub.3 CH.sub.3 O A-2 CH O.sub.3 --C(OCH.sub.3).sub.3 CH.sub.3 O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub. 3 O A-4 CH.sub.3 -- CH.sub.3__________________________________________________________________________ X.sub.2 Y.sub.3__________________________________________________________________________C(OCH.sub.3).sub.3 CH.sub.3 O A-5 CH.sub.3 OCH.sub.31,3-dioxolan- CH.sub.3 O A-5 CH.sub.3 SCH.sub.32-yl__________________________________________________________________________ X.sub.3__________________________________________________________________________C(CH.sub.3)(OCH.sub.3).sub.2 CH.sub.3 O A-6 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 O A-6 OCH --.sub.3 --__________________________________________________________________________ X.sub.4 Y.sub.4 Z__________________________________________________________________________1,3-dioxolan- CH.sub.3 O A-7 CH CH.sub.3 CH.sub.32-ylC(OCH.sub.3).sub.3 CH.sub.3 O A-7 OCH OCH.sub.3 CH.sub.3__________________________________________________________________________
TABLE VIa__________________________________________________________________________ General Structure VIa__________________________________________________________________________R.sub.1 R W A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree. C.__________________________________________________________________________1,3-dioxolan-2-yl H O A-2 CH.sub.2 O --1,3-dioxolan-2-yl H O A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl H O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl H O A-2 CH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H 0 2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dithiolan-2-yl H O A-2 CH.sub.3 O --1,3-dithiolan-2-yl H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H O A-3 CH.sub.3 -- --1,3-dioxolan-2-yl H O A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl H O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H O A-4 OCH.sub.3 -- H1,3-dioxolan-2-yl H O A-4 OCF.sub.2 H -- CH.sub.3C(OCH.sub.3).sub.3 CH.sub.3 O A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 CH.sub.3 O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 O A-4 CH.sub.3 -- CH.sub.3__________________________________________________________________________ X.sub.2 Y.sub.3__________________________________________________________________________C(OCH.sub.3).sub.3 CH.sub.3 O A-5 CH.sub.3 OCH.sub.31,3-dioxolan- CH.sub.3 O A-5 CH.sub.3 SCH.sub.32-yl__________________________________________________________________________ X.sub.3__________________________________________________________________________C(CH.sub.3)(OCH.sub.3).sub.2 CH.sub.3 O A-6 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 O A-6 OCH.sub.3 -- --__________________________________________________________________________ X.sub.4 Y.sub.4 Z__________________________________________________________________________1,3-dioxolan- CH.sub.3 O A-7 CH.sub.3 CH.sub.3 CH2-ylC(OCH.sub.3).sub.3 CH.sub.3 O A-7 OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE VIb__________________________________________________________________________ General Structure VIb__________________________________________________________________________R.sub.1 R W A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree. C.__________________________________________________________________________1,3-dioxolan-2-yl H O A-2 CH.sub.3 O --1,3-dioxolan-2-yl H O A-2 OCF.sub.2 H O --1,3-dioxolan-2-yl H O A-2 OCH.sub.3 O --1,3-dioxolan-2-yl H O A-2 CH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H O A-2 OC.sub.2 H.sub.5 CH.sub.2 --1,3-dithiolan-2-yl H O A-2 CH.sub.3 O --1,3-dithiolan-2-yl H O A-2 OCH.sub.3 CH.sub.2 --1,3-dioxolan-2-yl H O A-3 CH.sub.3 -- --1,3-dioxolan-2-yl H O A-3 OCH.sub.3 -- --1,3-dioxolan-2-yl H O A-4 CH.sub.3 -- CH.sub.31,3-dioxolan-2-yl H O A-4 OCH.sub.3 -- H1,3-dioxolan-2-yl H O A-4 OCF.sub.2 H -- CH.sub.3C(OCH.sub.3).sub.3 CH.sub.3 O A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 CH.sub.3 O A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 CH.sub.3 O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 O A-4 CH.sub.3 -- CH.sub.3__________________________________________________________________________ X.sub.2 Y.sub.3__________________________________________________________________________C(OCH.sub.3).sub.3 CH.sub.3 O A-5 CH.sub.3 OCH.sub.31,3-dioxolan- CH.sub.3 O A-5 CH.sub.3 SCH.sub.32-yl__________________________________________________________________________ X.sub.3__________________________________________________________________________C(CH.sub.3)(OCH.sub.3).sub.2 CH.sub.3 O A-6 CH.sub.3 -- --C(OCH.sub.3).sub.3 CH.sub.3 O A-6 OCH.sub.3 -- --__________________________________________________________________________ X.sub.4 Y.sub.4 Z__________________________________________________________________________1,3-dioxolan- CH.sub.3 O A-7 CH.sub.3 CH.sub.3 CH2-ylC(OCH.sub.3).sub.3 CH.sub.3 O A-7 OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE VII__________________________________________________________________________General Structure VIIR.sub.1 R R.sub.14 E W X Y Z m.p. .degree.C.__________________________________________________________________________C(OCH.sub.3).sub.3 H H -- O CH.sub.3 CH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O CH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O Cl OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O Br OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O CH.sub.3 H CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 H CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 CHC(OCH.sub.3).sub.3 H H -- O OCF.sub.2 H OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 CH(OCH.sub.3).sub.2 CHC(OCH.sub.3).sub.3 H H -- O CH.sub.3 OC.sub.2 H.sub.5 CHC(OCH.sub.3).sub.3 H H -- O CH.sub.3 CH.sub.2 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 CH.sub.2 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 C.sub.2 H.sub.5 CHC(OCH.sub.3).sub.3 H H -- O OC.sub.2 H.sub.5 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O OCF.sub.2 H OCF.sub.2 H CHC(OCH.sub.3).sub.3 H H -- O CH.sub.2 F OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O CH.sub.2 Cl OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O CF.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O Cl OC.sub.2 H.sub.5 CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.2 CH.sub.2 F OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.2 CF.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O CH.sub.3 OCH.sub.3 NC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 OCH.sub.3 NC(OCH.sub.3).sub.3 H H -- O CH.sub.3 CH.sub.3 NC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 cyclo- N propylC(OCH.sub.3).sub.3 H H -- O OC.sub.2 H.sub.5 NHCH.sub.3 NC(OCH.sub.3).sub.3 H H -- O OCH.sub.2 CF.sub.3 OCH.sub.3 NC(OCH.sub.3).sub.3 H H -- O OCH.sub.2 CH.sub.2 F CH.sub.3 NC(OCH.sub.3).sub.3 H H -- O OCH.sub.2 CH.sub.2 F OCH.sub.3 NC(OCH.sub.3).sub.3 H H -- S OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H 3-F -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H 5-Cl -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H 5-CH.sub.3 -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H 5-C.sub.2 H.sub.5 -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H 6-OCH.sub.3 -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H 6-OC.sub.2 H.sub.5 -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H 6-SCH.sub.3 -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H 6-SC.sub.2 H.sub.5 -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H 5-Br -- O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H CH.sub.2 O OCH.sub.3 OCH.sub.3 CHC(OC.sub.2 H.sub.5).sub.3 H H CH.sub.2 O CH.sub.3 CH.sub.3 CHC(OC.sub.2 H.sub.5).sub.3 H H CH.sub.2 O CH.sub.3 OCH.sub.3 CHC(OC.sub.2 H.sub.5).sub.3 H H CH.sub.2 O OCH.sub.3 OCH.sub.3 CHC(OC.sub.2 H.sub.5).sub.3 H H CH.sub.2 O Cl OCH.sub.3 CHC(OC.sub.2 H.sub.5).sub.3 H H CH.sub.2 O CH.sub.3 OCH.sub.3 NC(OC.sub.2 H.sub.5).sub.3 H H CH.sub.2 O OCH.sub.3 OCH.sub.3 NC(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H CH.sub.2 O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H CH.sub.2 O CH.sub.3 OCH.sub.3 CHC(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H CH.sub.2 O CH.sub.3 CH.sub.3 CHC(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H CH.sub.2 O Cl OCH.sub.3 CHC(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H CH.sub.2 O CH.sub.3 OCH.sub.3 NC(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H CH.sub.2 O OCH.sub.3 OCH.sub.3 NC(OCH.sub.3).sub.3 CH.sub.3 H CH.sub.2 O OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H CH.sub.2 O OCH.sub.2 CHF.sub.2 CH.sub.3 NC(OCH.sub.3).sub.3 H H CH.sub.2 O CH.sub.3 i-C.sub.3 H.sub.7 CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 N(OCH.sub.3)CH.sub.3 NC(OCH.sub.3).sub.3 H H -- O CH.sub.3 N(CH.sub.2).sub.3 NC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 CF.sub.3 CHC(OCH.sub.3).sub.3 H H -- O CH.sub.3 SCH.sub.3 NC(OCH.sub.3).sub.3 H H -- O CH.sub.3 OCH.sub.2 CH=CH.sub.2 NC(OCH.sub.3).sub.3 H H -- O CH.sub.3 OCH.sub.2 CH.tbd.CH NC(OCH.sub.3).sub.3 H H -- O CH.sub.3 CH.sub.2 SCH.sub.3 NC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 SCF.sub.2 H CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 1,3-dioxolan-2-yl CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 4-methyl-1,3- N dioxolan-2-ylC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 4-ethyl-1,3- CH dioxolan-2-ylC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 1,3-dithiolan-2-yl CHC(OCH.sub.3).sub.3 H H -- O OCH.sub.3 1,3-oxathiolan-2-yl NC(OCH.sub.3)(OC.sub.2 H.sub.5).sub.2 H H -- O OCH.sub.3 OCH.sub.3 CHC(OC.sub.2 H.sub.5)(OCH.sub.3).sub.2 H H -- O OCH.sub.3 OCH.sub.3 CH2-methoxy-1,3- H H -- O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl2-ethoxy-1,3- H H -- O OCH.sub.3 OCH.sub.3 CHdioxolan-2-yl__________________________________________________________________________
TABLE VIIa__________________________________________________________________________General Structure VIIaR.sub.1 R R.sub.14 E W A X.sub.1 Y.sub.1 Y.sub.2 m.p. .degree.C.__________________________________________________________________________C(OCH.sub.3).sub.3 H H -- O A-2 CH.sub.3 O --C(OCH.sub.3).sub.3 H H -- O A-2 OCH.sub.3 O --C(OCH.sub.3).sub.3 H H -- O A-2 OCH.sub.3 CH.sub.2 --C(OCH.sub.3).sub.3 H H -- O A-2 OCF.sub.2 H O --C(OC.sub.2 H.sub.5).sub.3 H H -- O A-2 CH.sub.3 O --C(OC.sub.2 H.sub.5).sub.3 H H -- O A-2 OCH.sub.3 O --C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H -- O A-2 CH.sub.3 O --C(OCH.sub.2 CH.sub.2 CH.sub.3).sub.3 H H -- O A-2 OCH.sub.3 O --C(OCH.sub.3).sub.3 H H -- O A-3 CH.sub.3 -- --C(OCH.sub.3).sub.3 H H -- O A-3 OCH.sub.3 -- --C(OCH.sub.3).sub.3 H H -- O A-4 CH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H -- O A-4 OCH.sub.3 -- CH.sub.3C(OCH.sub.3).sub.3 H H -- O A-4 OCH.sub.3 -- H X.sub.2 Y.sub.3C(OCH.sub.3).sub.3 H H -- O A-5 CH.sub.3 OCH.sub.3C(OCH.sub.3).sub.3 H H -- O A-5 CH.sub.3 SCH.sub.3C(OCH.sub.3).sub.3 H H -- O A-5 CH.sub.3 CH.sub.3 X.sub.3C(OCH.sub.3).sub.3 H H -- O A-6 CH.sub.3C(OCH.sub.3).sub.3 H H -- O A-6 OCH.sub.3 X.sub.4 Y.sub.4 ZC(OCH.sub.3).sub.3 H H -- O A-7 CH.sub.3 CH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O A-7 OCH.sub.3 OCH.sub.3 CHC(OCH.sub.3).sub.3 H H -- O A-7 OCH.sub. 3 OCH.sub.3 N__________________________________________________________________________
Formulations
Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 5% to 99% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
______________________________________ Active Weight Percent* Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 5-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 1-95 5-99 0-15High Strength 90-99 0-10 0-2Compositions______________________________________ *Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for wettable powder and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0.degree. C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection Agency for the use intended.
The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preferred granular carriers or by agglomeration techniques.
In the following examples, all parts are by weight unless otherwise indicated.
EXAMPLE 5
Wettable Powder
______________________________________3-(1,3-dioxolan-2-yl)-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-sulfonamide 80%sodium alkylnaphthalenesulfonate 2%sodium ligninsulfonate 2%synthetic amorphous silica 3%kaolinite 13%______________________________________
The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.
EXAMPLE 6
Wettable Powder
______________________________________N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1,3-dioxolan-2-yl)-2-thiophenesulfonamide 50%sodium alkylnaphthalenesulfonate 2%low viscosity methyl cellulose 2%diatomaceous earth 36%______________________________________
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.
EXAMPLE 7
High Strength Concentrate
______________________________________3-(1,3-dioxolan-2-yl)-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-sulfonamide 99%silica aerogel 0.5%synthetic amorphous silica 0.5%______________________________________
The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
EXAMPLE 8
Wettable Powder
______________________________________3-(1,3-dioxolan-2-yl)-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-sulfonamide 20%sodium alkylnaphthalenesulfonate 4%sodium ligninsulfonate 4%low viscosity methyl cellulose 3%attapulgite 69%______________________________________
The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
EXAMPLE 9
Oil Suspension
______________________________________N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1,3-dioxolan-2-yl)-2-thiophenesulfonamide 25%polyoxyethylene sorbitol hexaoleate 5%highly aliphatic hydrocarbon oil 70%______________________________________
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
EXAMPLE 10
Oil Suspension
______________________________________3-(1,3-dioxolan-2-yl)-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-sulfonamide 35%blend of polyalcohol carboxylic 6%esters and oil soluble petroleumsulfonatesxylene 59%______________________________________
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.
EXAMPLE 11
Aqueous Suspension
______________________________________3-(1,3-dioxolan-2-yl)-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-sulfonamide 40%polyacrylic acid thickener 0.3%dodecylphenol polyethyleneglycol ether 0.5%disodium phosphate 1%monosodium phosphate 0.5%polyvinyl alcohol 1.0%water 56.7%______________________________________
The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
EXAMPLE 12
Solution
______________________________________3-(1,3-dioxolan-2-yl)-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-sulfonamide 30%dimethylformamide 70%______________________________________
The ingredients are combined and stirred to produce a solution, which can be used for low volume applications.
EXAMPLE 13
Dust
______________________________________wettable powder of Example 6 10%Pyrophyllite (powder) 90%______________________________________
The wettable powder and the pyrophyllite diluent are thoroughly blended and then packaged. The product is suitable for use a a dust.
EXAMPLE 14
Low Strength Granule
______________________________________3-(1,3-dioxolan-2-yl)-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-sulfonamide 0.1%attapulgite granules 99.9%(U.S.S. 20-40 mesh)______________________________________
The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.
EXAMPLE 15
Granule
______________________________________Wettable Powder of Example 6 5%attapulgite granules 95%(U.S.S. 20-40 mesh: 0.84-0.42 mm)______________________________________
A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
EXAMPLE 16
Granule
______________________________________N--[](4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1,3-dioxolan-2-yl)-2-thiophenesulfonamide 80%wetting agent 1%crude ligninsulfonate salt (containing 10%5-20 of the natural sugars)attapulgite clay 9%______________________________________
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.
EXAMPLE 17
Extruded Pellet
______________________________________3-(1,3-dioxolan-2-yl)-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophene-sulfonamide 25%anhydrous sodium sulfate 10%crude calcium ligninsulfonate 5%sodium alkylnaphthalenesulfonate 1%calcium/magnesium bentonite 59%______________________________________
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
Utility
Test results indicate that the compounds of the present invention are active herbicides. They have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Alternatively, the subject compounds are useful to modify plant growth.
The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 5.0 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required.
The compounds of the invention may be used in combination with any other commercial herbicide; examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.
The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow. ##STR29##
Test A
Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugar beet, cotton, rice, wheat and purple nutsedge (Cyperus rotundus) tubers were planted and treated pre-emergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:
C=chlorosis or necrosis;
B=burn
D=defoliation
E=emergence inhibition;
G=growth retardation; and
H=formative effects.
U=unusual pigmentation
X=axillary stimulation
S=albinism
6Y=abscised buds or flowers.
TABLE A______________________________________ Compound 1 Compound 2Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 9C 10CCocklebur 9C 10CSicklepod 2C,5G 7GNutsedge 4G 10CCrabgrass 3C,8G 5C,9GBarnyardgrass 5C,9H 9CWild Oats 8G 5C,9GWheat 5G 6C,9GCorn 2C,9G 3C,9GSoybean 9C 9CRice 9C 9CSorghum 9G 5C,9GSugar beet 10C 9CCotton 9C 9CPRE-EMERGENCEMorningglory 9G 4C,9GCocklebur 8H 9HSicklepod 9G 9GNutsedge 0 10ECrabgrass 2C,5G 7GBarnyardgrass 3C,7H 9HWild Oats 6C,9G 5C,9GWheat 5G 4C,9GCorn 5C,9H 9GSoybean 9H 9HRice 10E 10ESorghum 5C,9H 6C,9HSugar beet 5C,9G 9CCotton 2C,9G 9G______________________________________ Compound 3 Compound 4Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 10C 10CCocklebur 4C,9H 9CVelvetleaf 9C 9CNutsedge 9C 8CCrabgrass 7H 7GBarnyardgrass 9C 9CCheatgrass 10C 6C,9GWild Oats 2C,5G 2GWheat 2G 2GCorn 7U,9C 10CSoybean 9C 9CRice 9C 9CSorghum 5C,9H 2U,8HSugar beet 9C 9CCotton 9C 9CPRE-EMERGENCEMorningglory 9C 9GCocklebur 7H 8HVelvetleaf 10C 9CNutsedge 10E 10ECrabgrass 2C,7G 4C,9GBarnyardgrass 9H 9HCheatgrass 4C,9H 3C,9HWild Oats 8G 8GWheat 2C,8H 8GCorn 9H 4C,9HSoybean 8H 9HRice 10E 10ESorghum 9H 3C,9HSugar beet 5C,9G 5C,9GCotton 9G 9G______________________________________ Compound 5 Compound 6Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 10C 10CCocklebur 9H 9CVelvetleaf 2C,7G 9CNutsedge 4G 9CCrabgrass 2G 2C,6GBarnyardgrass 9C 3C,9HCheatgrass 0 3C,8GWild Oats 0 0Wheat 0 0Corn 7U,9C 2C,8HSoybean 5C,9G 5C,9GRice 4C,8G 4C,9GSorghum 3C,9H 4C,9HSugar beet 9C 9CCotton 5C,9G 9CPRE-EMERGENCEMorningglory 9G 9HCocklebur 3H 8HVelvetleaf 5G 9GNutsedge 3G 2C,9GCrabgrass 2G 0Barnyardgrass 3C,7G 4C,9HCheatgrass 6G 3C,8GWild Oats 3G 5GWheat 2G 4GCorn 2C,9G 8GSoybean 2C,5G 9HRice 3C,8H 4C,9HSorghum 3C,9H 4C,8HSugar beet 5C,9G 9CCotton 2C,8G 9G______________________________________ Compound Compound Compound 7 8 9Rate kg/ha 0.05 0.05 0.05______________________________________POST-EMERGENCEMorningglory 6C,9G 9C 10CCocklebur 9C 10C 9CVelvetleaf 6C,9G 10C 9CNutsedge 6G 3G 4C,8GCrabgrass 5G 4G 0Barnyardgrass 4C,9H 4C,9H 8HCheatgrass 0 2C,3H 0Wild Oats 0 0 0Wheat 0 0 0Corn 2C,9G 5C,9G 1HSoybean 5C,9G 5C,9G 3H,9G,7XRice 7G 5G 6GSorghum 3C,9H 5C,9H 9HSugar beet 3C,9G 9C 9CCotton 9C 9C 9CPRE-EMERGENCEMorningglory 8H 8G 8GCocklebur 9H 5G 7GVelvetleaf 4C,8G 3C,8G 4GNutsedge 0 3G 3GCrabgrass 0 0 0Barnyardgrass 0 3C,7H 4GCheatgrass 3G 0 0Wild Oats 0 0 0Wheat 0 0 0Corn 2C,8H 3C,9H 4GSoybean 3C,8H 3C,8H 5HRice 3C,5H 3C,7G 0Sorghum 3C,9H 5C,9H 2C,7GSugar beet 5C,9G 5C,9G 7GCotton 3C,8G 8G 8G______________________________________
Claims
  • 1. A compound of the formula ##STR30## wherein Q is ##STR31## R is H or CH.sub.3 ; R.sub.1 is ##STR32## E is CH.sub.2 or a single bond; R.sub.2 is H, C.sub.1 -C.sub.2 alkyl or Cl;
  • R.sub.3 is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy;
  • R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl;
  • R.sub.6 and R.sub.7 are independently H or C.sub.1 -C.sub.2 alkyl;
  • W is O or S;
  • W.sub.1 is O or S;
  • Q.sub.1 and Q.sub.2 are independently O, S or NCH.sub.3 ; ##STR33## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3)alkylamino;
  • Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3)alkylamino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.5 alkylthioalkyl, C(O)R.sub.8, ##STR34## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3;
  • L.sub.1 and L.sub.2 are independently O or S;
  • R.sub.8 is H or CH.sub.3 ;
  • R.sub.9 and R.sub.10 are independently C.sub.1 -C.sub.2 alkyl;
  • R.sub.11 is C.sub.1 -C.sub.3 alkyl;
  • R.sub.12 is H, F, Cl, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 alkylsulfonyl, di(C.sub.1 -C.sub.2)alkylsulfamoyl or CO.sub.2 (C.sub.1 -C.sub.2 alkyl);
  • R.sub.13 is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F or NO.sub.2 ;
  • R.sub.14 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 haloalkoxy, Cl, Br, F, NO.sub.2, di(C.sub.1 -C.sub.3) alkylsulfamoyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3)alkylamino, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3 or CH.sub.2 CN.
  • Z is N;
  • X.sub.3 is CH.sub.3 or OCH.sub.3 ;
  • and their agriculturally suitable salts; provided that
  • (a) when R.sub.3 is C.sub.1 -C.sub.3 alkoxy, then Q.sub.1 and Q.sub.2 are oxygen;
  • (b) when R.sub.3 is H or C.sub.1 -C.sub.3 alkyl, then Q is Q-1 through Q-9;
  • (c) X or Y are other than OCF.sub.2 H;
  • (d) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of the substituents on Q is less than or equal to ten;
  • (e) when W is S, then A is A-1, R is H, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR35## (f) when E is CH.sub.2, then R.sub.14 is H, CH.sub.3, OCH.sub.3, Cl or NO.sub.2 and is not in the 4-position.
  • 2. A compound of claim 1 where R.sub.3 is H or C.sub.1 -C.sub.3 alkyl.
  • 3. A compound of claim 1 where R.sub.3 is C.sub.1 -C.sub.3 alkoxy.
  • 4. A compound of claim 2 where W is O; R is H; X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3 or CF.sub.3 ; and Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, (OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, ##STR36## SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3.
  • 5. A compound of claim 4 where Q.sub.1 and Q.sub.2 are identical and are O or S, R.sub.12 is H, C.sub.1 -C.sub.2 alkyl or Cl and R.sub.13 is H.
  • 6. A compound of claim 5 where A is A-1; Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, NHCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OCH.sub.3, cyclopropyl, C.tbd.CH or CH(OCH.sub.3).sub.2 ; and X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, or OCH.sub.2 CF.sub.3.
  • 7. A compound of claim 6 where Q.sub.1 and Q.sub.2 are O.
  • 8. A compound of claim 6 where Q.sub.1 and Q.sub.2 are S.
  • 9. A compound of claim 6 where Q is Q-1.
  • 10. A compound of claim 6 where Q is Q-2.
  • 11. A compound of claim 6 where Q is Q-3.
  • 12. A compound of claim 6 where Q is Q-4.
  • 13. A compound of claim 6 where Q is Q-5.
  • 14. A compound of claim 6 where Q is Q-6.
  • 15. A compound of claim 6 where Q is Q-7.
  • 16. A compound of claim 6 where Q is Q-8.
  • 17. A compound of claim 6 where Q is Q-9.
  • 18. A compound of claim 3 where W is O; R is H; X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3 or CF.sub.3 ; and Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, ##STR37## SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3.
  • 19. A compound of claim 18 where E is a single bond; R.sub.12 is H, C.sub.1 -C.sub.2 alkyl or Cl; R.sub.13 is H; and R.sub.14 is H, F, Cl, Br, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio and is not para to the sulfonylurea bridge.
  • 20. A compound of claim 19 where A is A-1; Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, NHCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OCH.sub.3, cyclopropyl, C.tbd.CH or CH(OCH.sub.3).sub.2 ; and X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, or OCH.sub.2 CF.sub.3.
  • 21. A compound of claim 20 where Q is Q-1.
  • 22. A compound of claim 20 where Q is Q-2.
  • 23. A compound of claim 20 where Q is Q-3.
  • 24. A compound of claim 20 where Q is Q-4.
  • 25. A compound of claim 20 where Q is Q-5.
  • 26. A compound of claim 20 where Q is Q-6.
  • 27. A compound of claim 20 where Q is Q-7.
  • 28. A compound of claim 20 where Q is Q-8.
  • 29. A compound of claim 20 where Q is Q-9.
  • 30. A compound of claim 20 where Q is Q-10.
  • 31. A compound of claim 1 which is 3-(1,3-dioxolan-2-yl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophenesulfonamide.
  • 32. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid inert diluent.
  • 33. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid inert diluent.
  • 34. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid inert diluent.
  • 35. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid inert diluent.
  • 36. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid inert diluent.
  • 37. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid inert diluent.
  • 38. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 18 and at least one of the following: surfactant, solid or liquid inert diluent.
  • 39. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 19 and at least one of the following: surfactant, solid or liquid inert diluent.
  • 40. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 20 and at least one of the following: surfactant, solid or liquid inert diluent.
  • 41. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.
  • 42. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.
  • 43. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.
  • 44. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.
  • 45. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 5.
  • 46. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 6.
  • 47. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 18.
  • 48. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 19.
  • 49. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 20.
Parent Case Info

This is a division of application U.S. Ser. No. 006,434 filed Jan. 23, 1987, now U.S. Pat. No. 4,753,672 which in turn is a division of application U.S. Ser. No. 754,709 filed July 16, 1985, now U.S. Pat. No. 4,659,369, which in turn is a continuation-in-part of application U.S. Ser. No. 644,259 filed Aug. 27, 1984, now abandoned.

US Referenced Citations (1)
Number Name Date Kind
4764203 Topfl et al. Aug 1988
Divisions (2)
Number Date Country
Parent 6434 Jan 1987
Parent 754709 Jul 1985
Continuation in Parts (1)
Number Date Country
Parent 644259 Aug 1984