TREA

Benzylsulfonylureas and arylsulfamoylureas

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  • Patent Grant
  • 4853025
  • Patent Number
    4,853,025
  • Date Filed
    Tuesday, February 16, 1988
    36 years ago
  • Date Issued
    Tuesday, August 1, 1989
    35 years ago
Information
Abstract
Benzylsulfonylureas and arylsulfamoylureas are useful as pre-emergent and post-emergent herbicides and as plant growth regulants.
Description

BACKGROUND OF THE INVENTION
European patent application No. 51,466, published May 12, 1982, discloses compounds of the formula ##STR1## where W is a substituted benzyl; Z is CH or N; X is CH.sub.3, OCH.sub.3, Cl; and Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, or N(CH.sub.3).sub.2. The compounds are disclosed to have pre- and post-emergent herbicidal activity and to be useful as plant growth regulators.
European patent application No. 71,441, published Feb. 9, 1983, discloses compounds of the formula ##STR2## where Z is CH or N; X is CH.sub.3 or OCH.sub.3 ; Y is Cl, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH(OCH.sub.3).sub.2, or ##STR3## and L is ##STR4## where R.sub.1 is H or C.sub.1 -C.sub.3 alkyl; R.sub.2 is H or CH.sub.3, R.sub.5 is H, CH.sub.3, OCH.sub.3, Cl, Br, NO.sub.2, CO.sub.2 R.sub.7, SO.sub.2 R.sub.8, OSO.sub.2 R.sub.9, SO.sub.2 NR.sub.10 R.sub.11 ; R.sub.6 is H or C.sub.1 -C.sub.3 alkyl; R.sub.6 ' is H or CH.sub.3 ; Q is O, S, or SO.sub.2 ; and Q.sub.1 is CR.sub.3 R.sub.4 or O.
Utility as a pre- or post-emergent herbicide and as a plant growth regulant is disclosed.
European patent application No. 79,683, published May 25, 1983, discloses compounds, useful as herbicides or plant growth regulants, of the formula ##STR5## where Z is CH or N; X and Y are as in European application No. 51,466 (described above) and J is ##STR6## Q is O, S or SO.sub.2 ; R is H or CH.sub.3 ;
R.sub.1 is H, CH.sub.3, OCH.sub.3, Cl, Br, CO.sub.2 R.sub.5, SO.sub.2 R.sub.6, OSO.sub.2 R.sub.7 or SO.sub.2 NR.sub.8 R.sub.9 ;
R.sub.2 and R.sub.3 are independently H or C.sub.1 -C.sub.3 alkyl;
R.sub.4 is H or CH.sub.3 ;
R.sub.5 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 Cl;
R.sub.6 is C.sub.1 -C.sub.3 alkyl;
R.sub.7 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; and
R.sub.8 and R.sub.9 are independently C.sub.1 -C.sub.2 alkyl.
SUMMARY OF THE INVENTION
The present invention relates to novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as pre-emergent or post-emergent herbicides or plant growth regulants. ##STR7## wherein J is ##STR8## n is 0 or 1; L is CH.sub.2 or O;
Q is CH.sub.2 or O;
Q.sub.1 is O, S or SO.sub.2 ;
Q.sub.2 is O or S;
R is H or CH.sub.3 ;
R.sub.1 is H, F, Cl, Br, CH.sub.3 or OCH.sub.3 ;
R.sub.2 is H or C.sub.1 -C.sub.3 alkyl;
R.sub.3 is H or CH.sub.3 ;
R.sub.4 is H or CH.sub.3 ;
R.sub.5 is H, CH.sub.3 or C.sub.2 H.sub.5 ;
R.sub.6 is H or CH.sub.3 ;
R.sub.7 is H or CH.sub.3 ;
R.sub.8 is F, Cl, Br, OCH.sub.3, SCH.sub.3, SO.sub.2 CH.sub.3, CO.sub.2 CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2 or OSO.sub.2 CH.sub.3 ;
R.sub.9 is H, OH, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxyalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.6 alkoxy, phenyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.1 -C.sub.6 alkylcarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, benzyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.3 -C.sub.6 alkylcarbonylalkyl, C.sub.3 -C.sub.6 alkoxycarbonylalkyl or C.sub.1 -C.sub.4 cyanoalkyl;
A is ##STR9## X is CH.sub.3, OCH.sub.3, Cl, Br, OCH.sub.2 CF.sub.3 or OCF.sub.2 H; Y is C.sub.1 -C.sub.3 alkyl, CH.sub.2 F, cyclopropyl, C.tbd.CH, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCH.sub.2 CH.sub.2 F, 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, CR(OCH.sub.3).sub.2, ##STR10## CR(OCH.sub.2 CH.sub.3).sub.2 or OCF.sub.2 H; Z is CH or N;
X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H;
Y.sub.1 is O or CH.sub.2 ;
X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ;
Y.sub.2 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 CH.sub.2 CH.sub.3 ;
X.sub.3 is CH.sub.3 or OCH.sub.3 ; and
Y.sub.3 is H or CH.sub.3 ;
provided that
(1) when X is Cl or Br, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; and
(2) when X or Y is OCF.sub.2 H, then Z is CH.
Compounds of formula I that are preferred for reasons of their higher herbicidal activity, greater plant growth regulant activity or more favorable ease of synthesis are:
(1) Compounds in which A is A-1.
(2) Compounds of the scope of (1) where Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, CH.sub.2 F or CF.sub.3 ; and L is CH.sub.2.
(3) Compounds of the scope of (2) where J is J.sub.1, J.sub.3, J.sub.7, J.sub.8, J.sub.15 or J.sub.16.
(4) Compounds of the scope of (3) where R is H; R.sub.1 is H; and X is CH.sub.3 or OCH.sub.3.
Compounds that are specifically preferred are
1,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-oxo-benzo[c]furan-7-methanesulfonamide;
1,3-dihydro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-1-oxo-benzo[c]furan-7-methanesulfonamide;
N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-benzo[B]thiophene-7-methanesulfonamide-1,1-dioxide; and
N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methyl-benzo[B]thiophene-7-methanesulfonamide-1,1-dioxide.
DETAILED DESCRIPTION OF THE INVENTION
Synthesis
The compounds of Formula I can be prepared as indicated by one or more of the methods shown below in Equations 1, 2, 3, and 4.
Equation 1 depicts the reaction of sulfonyl isocyanates of Formula II, where J is other than J.sub.19, with the appropriate heterocyclic amines, III, to give the desired products of Formula Ia. ##STR11## wherein J, X, Y and Z are as previously defined, R.sub.2 is C.sub.1 -C.sub.3 alkyl and R.sub.9 is other than H or OH.
The reaction of Equation 1 is best carried out in an inert aprotic solvent such as methylene chloride, tetrahydrofuran, or acetonitrile at a temperature between 20.degree. and 80.degree. C. A catalytic amount of 1,4-diazabicyclo[2,2,2]octane (DABCO) may be used to accelerate the reaction. In cases in which the products are insoluble in the reaction solvent, they may be isolated by simple filtration. When the products are soluble, they may be isolated by evaporation of the solvent and trituration of the residue with solvents such as 1-chlorobutane, diethyl ether, or methanol, and filtration.
Compounds of Formula Ib, where J is other than J.sub.3, J.sub.4, J.sub.5, J.sub.6, J.sub.8, J.sub.9, and J.sub.12, and where L is --CH.sub.2 --, can be prepared as shown in Equation 2 by treating sulfonamides of Formula IV with the methyl ester of a pyrimidine or triazinecarbamic acid of Formula V in the presence of an equimolar quantity of trimethylaluminum. ##STR12## wherein X, Y and Z are as previously defined and J is as defined above.
The reaction of Equation 2 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 96 hours under an inert atmosphere, as taught in European Pat. No. 84,244 (issued July 27, 1983). The methyl carbamates, V, can be conveniently synthesized by treatment of the corresponding heterocyclic amines of Formula III with dimethyl carbonate or methyl chloroformate in the presence of a base such as sodium hydride or pyridine.
Alternatively, compounds of Formula Ic, where J is other than J.sub.5, J.sub.6, J.sub.10, and J.sub.11, and where L is --CH.sub.2 --, can be prepared as shown below in Equation 3 by the reaction of sulfonamides of Formula IV with the phenyl ester of the appropriate carbamic acid, VI, in the presence of an equimolar quantity of a tertiary amine base such as 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU). ##STR13## wherein J, X, Y and Z are as previously defined.
The reaction shown in Equation 3 is carried out at about 23.degree. C. in a suitable solvent such as dioxane or acetonitrile. Aqueous acid work-up affords the desired products as described in European patent application No. 70,804 (published Jan. 26, 1983). The phenyl carbamates, VI, can be synthesized by treating the corresponding heterocyclic amines of Formula III with diphenyl carbonate or phenyl chloroformate in the presence of a base such as sodium hydride or pyridine.
Compounds of Formula Id, where J is other than J.sub.15, J.sub.17, and J.sub.19, and where L is O, can be prepared as shown below in Equation 4. The intermediate chlorosulfonylurea of Formula VII is formed by treatment of the corresponding heterocyclic amine, III, with commercially available chlorosulfonyl isocyanate and is then allowed to react with an appropriate phenol of Formula VIII. ##STR14## wherein J, X, Y and Z are as previously defined.
The reaction shown in Equation 4 is best carried out according to the methods taught in U.S. Pat. No. 4,391,976.
Sulfonyl isocyanates of Formula IIa, where J is other than J.sub.19, and R.sub.2 is C.sub.1 -C.sub.3 alkyl, R.sub.9 is other than hydrogen and hydroxy, and where L is --CH.sub.2 --, can be prepared as shown in Equation 5 by the reaction of the corresponding sulfonamides of general structure IV with phosgene in the presence of n-butyl isocyanate and a catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO). Alternatively, the sulfonyl isocyanates, IIa, may be prepared via phosgenation of the appropriate n-butylureas of Formula IX as represented in Equation 6. ##STR15## wherein J is as previously defined.
The reaction shown in Equation 5 is best carried out according to the procedure described in U.S. Pat. No. 4,238,621. ##STR16## wherein J is as previously defined.
The compounds of Formula IX are conveniently prepared by stirring a mixture of the appropriate sulfonamides, IV, anhydrous potassium carbonate, and n-butyl isocyanate in acetone or methyl ethyl ketone at 25.degree. to 80.degree. C. until all of the isocyanate has reacted. The products are isolated by quenching in dilute mineral acid and recrystallizing the solid product. The compounds IX are treated with phosgene and a catalytic amount of DABCO in refluxing xylene or chlorobenzene in a manner analogous to that described in Equation 5.
Another method for the preparation of sulfonyl isocyanates IIa is shown in Equation 7. Treatment of sulfonamides of Formula IV with thionyl chloride gives intermediate N-sulfinylsulfonamides, X, which afford sulfonyl isocyanates of Formula IIa upon exposure to phosgene in the presence of a catalytic amount of pyridine. ##STR17## wherein J is as previously defined.
The reaction of Equation 7 can best be performed according to the procedure of H. Ulrich, B. Tucker, and A. Sayigh, J. Org. Chem., 34, 3200 (1969).
Sulfonyl isocyanates of Formula IIb, where J is other than J.sub.15, J.sub.17 or J.sub.19, R.sub.2 is C.sub.1 -C.sub.3 alkyl, R.sub.9 is other than hydrogen and hydroxy, and L is O, can be most easily prepared as shown below in Equation 8 by the reaction of appropriately substituted phenols of Formula VIII with chlorosulfonyl isocyanate. This procedure is taught in U.S. Pat. Nos. 4,191,553 and 4,394,153, and by Lohaus in Chem. Ber., 105, 2791 (1972). ##STR18## wherein J is as previously defined.
The requisite sulfonamides of Formula IVa can be synthesized from the appropriately substituted benzyl chlorides or benzyl bromides, XI, by the three-step sequence of reactions outlined below in Equation 9. ##STR19## wherein X' is chlorine or bromine;
J is J.sub.1, J.sub.2, J.sub.3, J.sub.13, J.sub.14, J.sub.15, J.sub.16, J.sub.20, or J.sub.21 ;
L is --CH.sub.2 --; and
when J is J.sub.15 or J.sub.16, Q.sub.1 is SO.sub.2.
Equation 9(a)
The conversion of alkyl halides to isothiouronium salts is well precedented in the literature. For relevant examples, see T. B. Johnson and J. M. Sprague, J. Am. Chem. Soc., 58, 1348 (1936); 59, 1837 and 2439 (1937); 61, 176 (1939). In a typical procedure, a benzyl halide of Formula XI is treated with thiourea in a suitable solvent such as ethanol or tetrahydrofuran. Temperatures of 40.degree.-80.degree. C. over one-half to 4 hours are typically required to complete the reaction. The product salts, XII, are isolated by cooling and filtration or by concentration to remove the solvent. The salts, XII, are generally sufficiently pure to be carried on directly to step (9b) without further purification.
Equation 9(b)
The oxidative chlorination of isothiouronium salts to afford sulfonyl chlorides is most conveniently effected according to the procedure of Johnson as described in J. Am. Chem. Soc., 61, 2548 (1939). Thus, the appropriate isothiouronium salts, XII, are suspended in aqueous acetic acid and treated with at least three equivalents of chlorine at temperatures between 0.degree. and 20.degree. C. The product sulfonyl chlorides of Formula XIII are isolated by filtration or extraction into methylene chloride followed by drying and evaporation of the solvent. No further purification of the sulfonyl chlorides is necessary.
Equation 9(c)
In Equation (9c), the sulfonyl chlorides of Formula XIII are suspended in an aprotic solvent such as diethyl ether, 1-chlorobutane, methylene chloride, or tetrahydrofuran and contacted with an excess of anhydrous ammonia at a temperature of 0.degree. to 25.degree. C. The product sulfonamides of Formula IVa are isolated by filtration and washing with water to remove the by-product ammonium chloride, and concentrating the organic solution. Frequently, the crude sulfonamides may be used directly to prepare the sulfonyl isocyanates of Formula II. However, they may also be purified first by recrystallization from a suitable organic solvent such as ethanol, acetonitrile or chloroform.
Sulfonamides of Formula IVb can be prepared starting from the appropriate benzyl halides of Formula XI by the three-step sequence of reactions shown below in Equation 10. ##STR20## wherein X' is chlorine or bromine;
J is other than J.sub.2, J.sub.5, J.sub.6, J.sub.10 or J.sub.11 ; and
L is --CH.sub.2 --.
Equation 10(a)
The displacement reaction of Equation 10(a) is best carried out by treating the benzyl halides XI with sodium sulfite at reflux temperature for 3 to 12 hours in water or aqueous methanol. The solution is cooled and the solvent removed in vacuo to give a residue which is washed with methanol or ethyl acetate and filtered. Evaporation of the filtrate affords the sodium sulfonate salt which is typically carried directly on to the next step. For examples of this reaction, see Reed and Tarter, J. Am. Chem. Soc., 57, 571 (1935); and Latimer and Bost, J. Org. Chem., 5, 24 (1940).
Equation 10(b)
The reaction shown in Equation 10(b) can be effected by warming a mixture of the dried salts of Formula XIV with phosphorous pentachloride or phosphorous oxychloride according to the procedure of S. Hazlet, J. Am. Chem. Soc., 59, 287 (1937) or O. Billeter, Ber. Deut. Chem. Ges., 38, 2018 (1935). The product sulfonyl chlorides, XIII, are isolated either by distillation from the crude reaction mixture or by extraction into a suitable solvent such as methylene chloride or 1-chlorobutane.
Equation 10(c)
The amination reaction of Equation 10(c) is carried out as described above for Equation 9(c).
Benzyl halides of Formulas XIa and XIb (X'=Br or Cl) may be prepared as shown below in Equation 11 by treatment of the appropriately substituted toluene derivatives, XV, with either N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS). ##STR21## wherein X' is chlorine or bromine;
J is J.sub.7, J.sub.8, J.sub.9, J.sub.12, J.sub.17, J.sub.18, J.sub.19, J.sub.20 or J.sub.21 ;
L is --CH.sub.2 --;
R.sub.1 is H, F, Cl, Br or OCH.sub.3 ; and
when J is J.sub.8 or J.sub.12, R.sub.3 is H, and
when J is J.sub.17, R.sub.3 and R.sub.4 are H.
The reaction of Equation 11 can be most conveniently carried out by heating a solution of the toluene derivatives, XV, and either N-bromosuccinimide or N-chlorosuccinimide in a suitable solvent such as carbon tetrachloride at reflux temperature. A free radical catalyst such as azoisobutyronitrile or benzoyl peroxide is usually employed to initiate the reaction. When the reaction is complete, the cooled solution is filtered to remove the by-product succinimide and the filtrate concentrated in vacuo. The benzyl halides of Formulas XIa and XIb are often obtained in a sufficiently pure state for further transformation.
An alternate method for the preparation of benzyl chlorides of Formula XIb starting from the appropriate benzyl alcohols of Formula XVI is outlined below in Equation 12. ##STR22## wherein X' is chlorine;
J is other than J.sub.5, J.sub.6, J.sub.10 or J.sub.11 ; and
L is --CH.sub.2 --.
There exists a wide variety of well known methods for converting alkyl alcohols to the corresponding chlorides. One of the most common procedures involves treatment of the alcohols with thionyl chloride either alone or in the presence of a suitable base such as pyridine. For relevant examples, see the following references: H. Gilman and J. E. Kirby, J. Am. Chem. Soc., 51, 3475 (1929); H. Gilman and A. P. Hewlett, Rec. Trav Chim., 51, 93 (1932); or M. S. Newman, J. Am. Chem. Soc., 62, 2295 (1940).
The requisite benzyl alcohols of Formula XVI (shown below in Equation 13 for the specific example of J=J.sub.16) can be synthesized by reduction of the appropriately substituted benzoic acid derivatives of Formula XVII with diborane in a solvent such as tetrahydrofuran. ##STR23## wherein R.sub.1, R.sub.3, R.sub.4 and Q.sub.1 are as previously defined.
Although the reaction of Equation 13 is shown specifically for J=J.sub.16, this reduction is applicable to ring systems J.sub.1, J.sub.2, J.sub.3, J.sub.4, J.sub.13, J.sub.14, J.sub.15, J.sub.18, J.sub.19, J.sub.20 and J.sub.21 where L is --CH.sub.2 --. For a description of the use of diborane for reduction of benzoic acid derivatives, see H. C. Brown, J. Org. Chem., 38, 2786 (1973).
Alternatively, benzyl alcohols of Formula XVI (shown below in Equation 14 for the specific example of J=J.sub.16) can be synthesized by reduction of the appropriately substituted benzaldehyde derivatives of Formula XVIII with sodium borohydride in a solvent such as ethanol. ##STR24## wherein R.sub.1, R.sub.3, R.sub.4 and Q.sub.1 are as previously defined.
Although the reaction of Equation 14 is shown specifically for J=J.sub.16, this reduction is applicable to ring systems J.sub.1, J.sub.2, J.sub.3, J.sub.4, J.sub.7, J.sub.8, J.sub.9, J.sub.12, J.sub.13, J.sub.14, J.sub.15, J.sub.17, J.sub.18, J.sub.19, J.sub.20 and J.sub.21 where L is --CH.sub.2 --. For a description of the use of sodium borohydride for the selective reduction of aldehydes, see S. Chaikin and W. Brown, J. Am. Chem. Soc., 71, 122 (1949).
The aldehydes of Formula XVIII can be prepared by the procedure shown in Equation 15 starting with the appropriate nitriles of Formula XIX (shown for the specific example of J=J.sub.16). ##STR25## wherein R.sub.1, R.sub.3, R.sub.4 and Q.sub.1 are as previously defined.
Although the reaction of Equation 15 is shown specifically for J=J.sub.16, this transformation is equally applicable to all of the ring systems (L=--CH.sub.2 --) except J.sub.5, J.sub.6, J.sub.10, and J.sub.11. The reaction shown in Equation 15 can be carried out according to the procedures of H. C. Brown, C. J. Shoaf, and C. P. Garg, Tetrahedron Lett., 9 (1959), and J. A. Marshall, N. H. Andersen, and J. W. Schlicher, J. Org. Chem., 35, 858 (1970).
Benzoic acid derivatives of Formula XVII (shown below in Equation 16 for the specific example of J=J.sub.16) can be prepared by hydrolysis of the appropriate nitriles of Formula XIX which are, in turn, prepared by a Sandmeyer reaction on the corresponding aniline derivatives XX. ##STR26## wherein R.sub.1, R.sub.3, R.sub.4 and Q.sub.1 are as previously defined.
As before, while the reactions of Equation 16 are shown specifically for J=J.sub.16, these steps are applicable to all ring systems where J is other than J.sub.5, J.sub.6, J.sub.10 or J.sub.11, and L is --CH.sub.2 --.
Equation 16(a)
The diazotization and cuprous cyanide coupling reaction of Equation 16(a) is best carried out according to the procedure described in Organic Syntheses, Coll. Vol. I, p. 514.
Equation 16(b)
Nitriles of Formula XIX are most easily hydrolyzed to the desired carboxylic acids XVII by heating at reflux temperature in concentrated solutions of sulfuric acid or by treatment with 100% phosphoric acid and subsequent exposure to nitrous acid. The products are typically isolated by extraction into aqueous base solution followed by washing with a suitable organic solvent such as ether and acidification of the water layer. For a compilation of references dealing with this process, see R. Wagner and H. Zook, "Synthetic Organic Chemistry," John Wiley & Sons, Inc., New York, 1953, p. 412.
A method similar to that described in Equation 16 above can be applied to the synthesis of phenols of Formula VIII as shown below in Equation 17 (shown for the specific example of J=J.sub.16). ##STR27## wherein R.sub.1, R.sub.3, R.sub.4 and Q.sub.1 are as previously defined.
The reaction of Equation 17 is applicable to ring systems J.sub.1, J.sub.2, J.sub.3, J.sub.4, J.sub.5, J.sub.6, J.sub.7, J.sub.8, J.sub.9, J.sub.10, J.sub.11, J.sub.12, J.sub.13, J.sub.14, J.sub.16, J.sub.18, J.sub.20 and J.sub.21 where L is 0. The diazotization and hydrolysis reactions shown in Equation 17 can be carried out according to the following procedures: Stevens and Beutel, J. Am. Chem. Soc., 63, 311 (1941); Grillot and Gormley, J. Am. Chem. Soc., 67, 1968 (1945); and Mosettig and Stuart, J. Am. Chem. Soc., 61, 1 (1939).
The requisite aniline derivatives of Formula XX can be prepared in a straightforward manner by reduction of the corresponding nitro compounds of Formula XXI as shown in Equation 18 (for the example where J=J.sub.16). ##STR28## wherein R.sub.1, R.sub.3, R.sub.4, and Q are as previously defined.
Although the reaction of Equation 18 is shown specifically for J=J.sub.16, this reduction is applicable to all ring systems J.sub.1 -J.sub.21. There exists a wide variety of methods for effecting the reduction of aromatic nitro groups to the corresponding aniline derivatives. One of the more common procedures involves treating the nitro compounds of Formula XXI with a slight excess of stannous chloride dihydrate in concentrated hydrochloric acid solution at temperatures between 25.degree. and 80.degree. C. Alternatively, reduction may be accomplished with iron powder in glacial acetic acid solution as described by Hazlet and Dornfeld, J. Am. Chem. Soc., 66, 1781 (1944), and by West in J. Chem. Soc., 127, 494 (1925). For a general review, see Groggins, "Unit Processes In Organic Synthesis," McGraw-Hill Book Co., New York, 1947, pp. 73-128.
Many of the substituted aromatic nitro compounds of Formula XXI (where it is understood that all ring systems defined in the Summary of Invention are represented) can be synthesized by methods taught in U.S. patent application Ser. No. 499,443, filed on May 31, 1983, or by any of several possible synthetic routes known to one skilled in the art.
The intermediate functionalized toluene derivatives of Formula XV (L+--CH.sub.2 --) may also be prepared by straightforward synthetic routes known to one skilled in the art.
The synthesis of heterocyclic amines such as these depicted by Formula III has been reviewed in "The Chemistry of Heterocyclic Compounds," a series published by Interscience Publ., New York and London. Aminopyrimidines are described by D. J. Brown in "The Pyrimidines," Vol. XVI of the series mentioned above. The 2-amino-1,3,5-triazines can be prepared according to the method described by E. M. Smolin and L. Rapaport in "s-Triazines and Derivatives," Vol. XIII.
Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be made by similar techniques. Detailed examples of such techniques are given in U.S. Pat. No. 4,127,405.





The compounds of this invention and their preparation are further illustrated by the following examples wherein temperatures are given in degrees centigrade and all parts are by weight unless otherwise designated.
EXAMPLE 1
2,6-Dimethylbenzoic acid, methyl ester
A solution of 10 g of 2,6-dimethylbenzoic acid in 22 g thionyl chloride was stirred at reflux temperature for 2 hours. Removal of the excess thionyl chloride afforded the crude acid chloride as a yellow oil. This intermediate was added to a stirred solution of 4 mL of methanol in 10.8 mL pyridine at 65.degree.-70.degree. C. After completion of the addition, the resulting mixture was stirred at room temperature for 2 hours and then poured into 75 mL ice-water. The aqueous layer was extracted with four 50-mL portions of ether and the combined organic extracts were back-washed with saturated sodium bicarbonate solution, 5% aqueous hydrochloric acid, and water. Drying and evaporation of the solvent gave a pale yellow oil which was purified by bulb-to-bulb distillation (40.degree.-50.degree. C., 0.5 mm Hg) to afford 9.5 g of pure 2,6-dimethylbenzoic acid, methyl ester as a colorless liquid; IR (film) 1725 cm.sup.-1 ; NMR(CDCl.sub.3) .delta. 2.3 (s, 6H), 3.9 (s, 3H), 7.0-7.4 (m, 3H).
EXAMPLE 2
2,6-Bis(.alpha.,.alpha.'-bromomethyl)benzoic acid, methyl ester
A mixture of 5.0 g of the product from Example 1, 11.1 g of N-bromosuccinimide and 0.1 g of azoisobutyronitrile in 76 mL carbon tetrachloride was heated at reflux temperature for one hour. The solution was cooled to room temperature, filtered, and the filtrate concentrated in vacuo to give a light orange oil. Treatment with ether-hexane (1:1, v/v) afforded 3.0 g of pure 2,6-bis(.alpha.,.alpha.'-bromomethyl)benzoic acid, methyl ester as a white solid, m.p. 67.degree.-70.degree. C.; IR(nujol) 1720 cm.sup.-1 ; NMR(CDCl.sub.3) .delta. 4.0 (s, 3H), 4.65 (s, 4H), 7.5 (s, 3H).
EXAMPLE 3
7-Bromomethylphthalide
The product from Example 2 (2.0 g) was added to 8 mL of concentrated sulfuric acid and the suspension was warmed to about 60.degree. C. for 3 hours. The solution was allowed to cool and was poured into ice-water. The resulting white precipitate was collected by filtration, washed well with water and dried. Recrystallization from acetone gave 1.0 g of pure 7-bromomethylphthalide as a white powder, m.p. 127.5.degree.-131.degree. C.; IR(KBr) 1755 cm.sup.-1 ; NMR(CDCl.sub.3) .delta. 5.0 (s, 2H), 5.29 (s, 2H), 7.4 (br d, 1H), 7.5 (br d, 1H), 7.6 (dd, 1H).
EXAMPLE 4
7-[[(Amino)(imino)methyl]thiomethyl]phthalide
A solution of 1.0 g of the product from Example 3 in 10 mL tetrahydrofuran was treated with 0.33 g of thiourea and the suspension was warmed to reflux temperature for 15 minutes as a thick, white precipitate formed. The reaction mixture was allowed to cool and was filtered. The collected solid was washed with 1-chlorobutane and dried. The yield of the pure title compound was 1.2 g as a white powder, m.p. 206.degree.-211.degree. C. (dec.); NMR(DMSO-d.sub.6) .delta. 4.8 (s, 2H), 5.4 (s, 2H), 7.61 (br t, 2H), 7.73 (br t, 1H), 9.1 (brs, 1H), 9.23 (br s, 2H).
EXAMPLE 5
1,3-Dihydro-1-oxo-benzo[c]furan-7-methanesulfonyl chloride
A solution of 9.4 g of the product from Example 4 in 77 mL of 50% aqueous acetic acid was cooled to 0.degree. C. and treated with 8 mL of liquid chlorine. Following the addition, the mixture was stirred at 0.degree.-10.degree. C. for 2 hours, filtered, and the solid was washed well with water. The yield of 1,3-dihydro-1-oxo-benzo[c]furan-7-methanesulfonyl chloride was 5.6 g as an off-white solid, m.p. 103.degree.-105.5.degree. C. (dec); IR(KBr) 1740, 1355, 1200 cm.sup.-1.
EXAMPLE 6
1,3-Dihydro-1-oxo-benzo[c]furan-7-methanesulfonamide
A solution of 5.6 g of the product from Example 5 in 50 mL tetrahydrofuran was cooled to 0.degree. C. under an atmosphere of nitrogen and was treated with 1.5 mL of anhydrous ammonia. The resulting suspension was stirred at room temperature for 3 hours. The insoluble solids were collected by filtration and were washed with water and dried. The yield of the title compound was 3.8 g as a white powder, m.p. 192.degree.-195.degree. C.; IR(KBr) 3340, 3240, 1740, 1130 cm.sup.-1 ; NMR(DMSO-d.sub.6 /CDCl.sub.3) .delta. 4.9 (s, 2H), 5.4 (s, 2H), 6.7 (br s, 2H) 7.5-7.8 (m, 3H).
EXAMPLE 7
1,3-Dihydro-1-oxo-benzo[c]furan-7-methanesulfonyl isocyanate
A solution of 2.0 g of the product from Example 6 in 25 mL thionyl chloride was heated at reflux temperature for 18 hours. The reaction solution was allowed to cool to room temperature and excess thionyl chloride was removed in vacuo. The resulting residue was treated with 16 g of 10% phosgene in toluene and 5 drops of pyridine. This mixture was stirred at reflux temperature for 3 hours. The solution was allowed to cool, filtered under a stream of nitrogen, and the filtrate was concentrated to give 1,3-dihydro-1-oxobenzo[c]furan-7-methanesulfonyl isocyanate as an orange oil. The infrared spectrum of this compound displayed a characteristic isocyanate stretching absorption at 2240 cm.sup.-1 as well as a carbonyl stretching signal at 1750 cm.sup.-1.
EXAMPLE 8
1,3-Dihydro-N-[(4,6-dimethoxyprimidine-2-yl)aminocarbonyl]-1-oxo-benzo[c]furan-7-methanesulfonamide
A solution of 8 mmole of the product from Example 7 in 16 mL dry acetonitrile was treated with 1.2 g of 2-amino-4,6-dimethoxypyrimidine and the mixture was heated to 45.degree.-50.degree. C. under an atmosphere of nitrogen for 2 hours. After being stirred at room temperature for an additional 12 hours, the suspension was filtered and the collected solid was washed well with warm acetonitrile. The yield of the title compound was 1.0 g as a yellow powder, m.p. 181.degree.-184.degree. C. (dec.); IR(KBr) 1765, 1710, 1620, 1355 cm.sup.-1 ; NMR(CDCl.sub.3) .delta. 3.83 (s, 6H), 5.27 (s, 2H), 5.41 (s, 2H), 5.76 (s, 1H), 7.35 (br s, 1H), 7.5 (m, 1H), 7.7 (m, 2H), 12.4 (br s, 1H).
______________________________________General Formulas for Tables 1-7______________________________________General Formula 1 ##STR29##General Formula 1a ##STR30##General Formula 2 ##STR31##General Formula 2a ##STR32##General Formula 3 ##STR33##General Formula 4 ##STR34##General Formula 5 ##STR35##General Formula 6 ##STR36##General Formula 7 ##STR37##______________________________________
By applying the procedures of Examples 1 through 8, the compounds shown in Tables 1 and 2, following, can be prepared.
TABLE 1__________________________________________________________________________General Formula 1 m.p.J n L R.sub.1 R.sub.9 X Y (.degree.C.)__________________________________________________________________________J.sub.1 0 CH.sub.2 H CH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5J.sub.1 0 CH.sub.2 H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 Cl OCH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 Br OCH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.2 FJ.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 CF.sub.3J.sub.1 1 CH.sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub. 2 H -n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H H CH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H H OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H H CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H H OCH.sub.3 ClJ.sub.1 0 O H H CH.sub.3 CH.sub.3J.sub.1 0 O H H CH.sub.3 OCH.sub.3J.sub.1 0 O H H OCH.sub.3 OCH.sub.3J.sub.1 0 O H H OCH.sub.3 ClJ.sub.1 0 O H CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 O H CH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 O H CH.sub.3 CH.sub.3 CH.sub.3J.sub.1 0 O H CH.sub.3 Cl OCH.sub.3J.sub.1 0 O H CH.sub.3 Br OCH.sub.3J.sub.1 0 O H C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.1 0 O H -n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J.sub.1 0 O H CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J.sub.1 1 O H CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 5-F CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 6-Cl CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 6-Br CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 6-CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 6-OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 O H CH.sub.3 OCH.sub.2 CF.sub.3 CH.sub.3J.sub.1 0 O H CH.sub.3 OCHF.sub.2 OCH.sub.3J.sub.1 0 O H CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 cyclopropylJ.sub.1 0 O H CH.sub.3 OCH.sub.3 C.tbd.CHJ.sub.1 0 O H CH.sub.3 OCH.sub.3 NH.sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 OCH.sub.2 CH.sub.2 FJ.sub.1 0 O H CH.sub.3 OCH.sub.3 SCH.sub.3J.sub.1 0 O H CH.sub.3 OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2J.sub.1 0 O H CH.sub.3 OCH.sub. 3 OCH.sub.2 CH.sub.2 OCH.sub.3J.sub.1 0 O H CH.sub.3 OCH.sub.3 OCH.sub.2 C.tbd.CHJ.sub.1 0 O H CH.sub.3 OCH.sub.3 CH(OCH.sub.3).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 1,3-dioxolan- 2-ylJ.sub.1 0 O H CH.sub.3 OCH.sub.3 2-methyl-1,3- dioxolan-2-ylJ.sub.1 0 O H CH.sub.3 OCH.sub.3 CH(OC.sub.2 H.sub.5).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 C(CH.sub.3)(OC.sub.2 H.sub.5).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 NHCH.sub.3J.sub.1 0 O H CH.sub.3 Cl NHCH.sub.3J.sub.1 0 O H --CH.sub.2 CN OCH.sub.3 OCH.sub.3J.sub.1 0 O H --(CH.sub.2).sub.3 CN CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H OH CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --(CH.sub.2).sub.3 CH(CH.sub.3).sub.2 Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --CF.sub.2 H OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 CH.sub.2 Cl Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --(CH.sub.2).sub.5 Cl CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 OCH.sub.3 Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --(CH.sub.2).sub.4 OCH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 CH=CH.sub.2 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 CH=CHCH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 C.tbd.CH OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 C.tbd.C--CH.sub.3 Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --(CH.sub.2).sub.4 C.tbd.CH CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --OCH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --O(CH.sub.2).sub.4 CH.sub.3 Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --C.sub.6 H.sub.5 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H cyclopropyl OCH.sub.3 OCH.sub. 3J.sub.1 0 CH.sub.2 H cyclohexyl OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H cyclopropylmethyl OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H cyclohexylmethyl Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --C(O)CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --C(O)(CH.sub.2).sub.5 H Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --CO.sub.2 C.sub.2 H.sub.5 Br OCH.sub.3J.sub.1 0 CH.sub.2 H --CO.sub.2 (CH.sub.2).sub.4 H Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 C.sub.6 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 --CH=CH--CH.sub.2 Cl CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 C.tbd.C--CH.sub.2 Cl Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 C(O)CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH(CH.sub.3)CO.sub.2 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H H CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H H CH.sub. 3 CH.sub.3J.sub.1 0 CH.sub.2 H H Cl OCH.sub.3J.sub.1 0 O H H OCH.sub.3 OCH.sub.3J.sub.1 0 O H H CH.sub.3 OCH.sub.3J.sub.1 0 O H H CH.sub.3 CH.sub.3J.sub.1 0 O H H Cl OCH.sub.3J.sub.1 0 CH.sub.2 H -n-C.sub.4 H.sub.9 CH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H -n-C.sub.4 H.sub.9 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H -n-C.sub.4 H.sub.9 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H -n-C.sub.4 H.sub.9 Cl OCH.sub.3J.sub.1 0 O H -n-C.sub.4 H.sub.9 CH.sub.3 CH.sub.3J.sub.1 0 O H -n-C.sub.4 H.sub.9 CH.sub.3 OCH.sub.3J.sub.1 0 O H -n-C.sub.4 H.sub.9 OCH.sub.3 OCH.sub.3J.sub.1 0 O H -n-C.sub.4 H.sub.9 Cl OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 Cl OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 Br OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5J.sub.7 -- CH.sub.2 H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.2 FJ.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CF.sub.3J.sub.7 -- CH.sub.2 H H OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H -n-C.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3J.sub.7 -- O H CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 7-Cl CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- O 7-Br CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 6-F CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- O 7-CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- O 7-OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.2 CF.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCHF.sub.2 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 cyclopropylJ.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 NHCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.2 CH=CH.sub.2J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH(OCH.sub.3).sub.2J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 1,3-dioxolan- 2-ylJ.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH(OC.sub.2 H.sub.5)2J.sub.7 -- CH.sub.2 H CH.sub.3 Cl NHCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 --C.tbd.CHJ.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2J.sub.7 -- CH.sub.2 H OH OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H (CH.sub.2).sub.2 CH(CH.sub.3).sub.2 Cl OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH.sub.2 Cl OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H (CH.sub.2).sub.5 Cl CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 OCH.sub.3 Cl OCH.sub.3J.sub.7 -- CH.sub.2 H (CH.sub.2).sub.2 OCH.sub.3 Cl OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH=CH.sub.2 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH=CHCH.sub.2 Cl CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH=CHCH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 C.tbd.CCH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H OCH.sub.3 Cl OCH.sub.3J.sub.7 -- CH.sub.2 H O(CH.sub.2).sub.4 CH.sub.3 Cl OCH.sub.3J.sub.7 -- CH.sub.2 H C.sub.6 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H cyclopropyl Cl OCH.sub.3J.sub.7 -- CH.sub.2 H cyclopentyl OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H C(O)CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 C.sub.6 H.sub.5 Cl OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH=CHCl Cl OCH.sub.3J.sub.7 -- CH.sub.2 H CH(CH.sub.3)CO.sub.2 CH.sub.3 Cl OCH.sub.3__________________________________________________________________________
TABLE 1a General Formula 1a J n L Q Q.sub.1 Q.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 R.sub.7 R.sub.8 X Y m.p. (.degree.C.) J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- Br OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH.sub.2 F J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CF.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H H -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H C.sub.2 H.sub.5 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H -n-C.sub.3 H.sub.7 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH(CH.sub.3).sub.2 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- C1 OCH.sub.3 J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- Br OCH.sub.3 J.sub.2 1 O -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 O -- -- -- H C.sub.2 H.sub.5 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- 6-Br CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- 6-Cl CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- 5-F CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 O -- -- -- 6-CH.sub.3 CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub. 3 J.sub.2 0 O -- -- -- 6-OCH.sub.3 CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 181-184,d J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 OCH.sub.3 180-185,d J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- Cl OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(CH.sub.3).sub.2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl NHCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl OCF.sub.2 H J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.2 CF.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCF.sub.2 H OCF.sub.2 H J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 cyclopropyl J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).su b.2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 1,3-dioxolan- 2-yl J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(OC.sub.2 H.sub.5).sub.2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCF.sub.2 H OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 1,3-dioxolan- 2-yl J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 OCH.sub.2 C.tbd.CH J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- Br OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 CH.sub.2 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.2 F J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 CF.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- Cl OCH.sub.3 J.sub.3 1 O -- -- -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 1 O -- -- -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.3 1 O -- -- -- H -- CH.sub.3 H -- -- -- -- Cl OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- Cl OCH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- Br OCH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- Cl OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- 5-F -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- 6-Cl -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- 6-Br -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 O -- -- -- 5-CH.sub.3 -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 O -- -- -- 6-OCH.sub.3 -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 1 O -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.4 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.4 1 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.4 0 O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.4 1 O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.4 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.4 0 O -- -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 CH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl OCH.sub.3 J.sub.5 1 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.5 0 -- -- -- -- H H -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl OCH.sub.3 J.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.6 0 -- -- -- -- H H -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.6 1 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- Cl OCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- Br OCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.2 F J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CF.sub.3 J.sub.8 -- O -- -- -- H -- H -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.8 -- O -- -- -- H -- H -- -- -- -- -- Cl OCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- 7-Cl -- H -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.9 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.9 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.9 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.10 -- -- -- -- -- H CH.sub. 3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl OCH.sub.3 J.sub.10 -- -- -- -- -- H C.sub.2 H.sub.5 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.11 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.11 -- -- -- -- -- H C.sub.2 H.sub.5 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- Cl OCH.sub.3 J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- Br OCH.sub.3 J.sub.12 -- CH.sub.2 -- -- -- H -- CH.sub.3 -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- Cl OCH.sub.3 J.sub.12 -- O -- -- -- H -- CH.sub.3 -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.13 -- CH.sub.2 O -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.13 -- CH.sub.2 O -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.13 -- O O -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.13 -- O O -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.13 -- O CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.13 -- O CH.sub.2 -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.14 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.14 -- O -- -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- O -- H -- HH CH.sub.3 -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- O -- H -- HH CH.sub.3 -- -- -- Cl OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- Br OCH.sub.3 J.sub.15 -- -- -- O -- H -- H H CH.sub.3 -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- O -- H -- H H C.sub.2 H.sub.5 -- -- -- OCH.sub.3 CF.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 CH.sub.3 H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- Cl OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- Br OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.2 F J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CF.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- Cl OCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- Br OCH.sub.3 J.sub.15 -- -- -- S -- H -- H CH.sub.3 CH.sub.3 -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 222-222.5 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.3 208-209 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- CH.sub.3 CH.sub.3 192-193 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- Cl OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- Br OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.2 F J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CF.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub. 3 CH.sub.3 H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- Cl OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- Br OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.2 F J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CF.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- OCH.sub. 3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- Cl OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- 6-Cl CH.sub.3 H H H -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- 6-Cl CH.sub.3 H H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- 6-Cl CH.sub.3 H H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- 6-Cl CH.sub.3 H H H -- -- -- Cl OCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.3 J.sub. 15 -- -- -- S -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H CH.sub.3 -- -- -- Cl OCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H CH.sub.3 -- -- -- Br OCH.sub.3 J.sub.15 -- -- -- O -- 6-Cl -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- 5-Br -- H H CH.sub.3 -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- 6-F -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- 5-CH.sub.3 -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- 6-OCH.sub.3 -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- S -- 6-Cl -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.16 -- CH.sub.2 -- O -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.16 -- CH.sub.2 -- S -- H -- H CH.sub.3 -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- Cl OCH.sub.3 J.sub.17 -- -- -- -- O H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.17 -- -- -- -- S H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.17 -- -- -- -- O H -- CH.sub.3 CH.sub.3 -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.17 -- -- -- -- O H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- H H -- OCH.sub.3 OCH.sub.3 J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- CH.sub.3 H -- Cl OCH.sub.3 J.sub.18 -- O -- -- -- H -- H H -- H CH.sub.3 -- OCH.sub.3 OCH.sub.3 J.sub.19 -- -- -- -- -- H -- CH.sub.3 CH.sub.3 -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- Cl OCH.sub.3 J.sub.19 -- -- -- -- -- H -- CH.sub.3 CH.sub.3 -- -- -- -- Cl OCH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- 7-Cl -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- Cl OCH.sub.3 J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- F OCH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl Cl OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Br OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SCH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl Br OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 CH.sub.2 F J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl CH.sub.3 OC.sub.2 H.sub.5 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 C.sub.2 H.sub.5 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- F OCH.sub.3 OCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 OCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Br Cl OCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SCH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 Cl OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 Br OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.2 F J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub. 3 CF.sub.3 J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- Cl NHCH.sub.3 J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- Cl OCF.sub.2 H J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- Cl N(CH.sub.3).sub.2 J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 cyclopropyl J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(CH.sub.3).sub.2 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl NHCH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl OCF.sub.2 H J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl N(CH.sub.3).sub.2 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 cyclopropyl J.sub.5 0 -- -- -- -- H CH.sub. 3 -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 C.tbd.CH J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl OCF.sub.2 H J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3 ).sub.2 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 1,3-dioxolan- 2-yl J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(CH.sub.3).sub.2 J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 cyclopropyl J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl N(CH.sub.3).sub.2 J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl N(CH.sub.3).s ub.2 J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- Cl NHCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 C.tbd.CH J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 1,3-dioxola n- 2-yl J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 cyclopropyl J.sub.9 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub. 9 -- O -- -- -- H -- -- -- -- -- -- -- Cl N(CH.sub.3).sub.2 J.sub.9 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl NHCH.sub.3 J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl OCH.sub.3 J.sub.11 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- Cl OCH.sub.3 J.sub.11 -- -- -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.12 -- O -- -- -- H -- -- -- -- -- -- -- Cl NHCH.sub.3 J.sub.12 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.12 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 1,3-dioxolan- 2-yl J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.tbd.CH J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.2 CF.sub.3 OCH.sub.3 J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCHF.sub.2 OCHF.sub.2 J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.15 -- -- -- O -- H -- H H H -- -- -- OCH.sub.3 C.tbd.CH J.sub.15 -- -- -- O -- H -- H H H -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CHCl J.sub.15 -- -- -- O -- H -- H H H -- -- -- Cl NHCH.sub.3 J.sub.15 -- -- -- O -- H -- H H CH.sub.3 -- -- -- Cl N(CH.sub. 3).sub.2 J.sub.15 -- -- -- O -- H -- H H CH.sub. 3 -- -- -- OCH.sub.3 cyclopropyl J.sub.15 -- -- -- O -- H -- H H CH.sub.3 -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.15 -- -- -- O -- H -- CH.sub.3 CH.sub.3 H -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 CH.sub.3 H -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.2 C.tbd.CH J.sub.15 -- -- -- O -- H -- CH.sub.3 CH.sub.3 H -- -- -- OCH.sub.3 SCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 cyclopropyl J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- Cl N(CH.sub.3).sub.2 J.sub.15 -- -- -- S -- H -- CH.sub.3 CH.sub.3 CH.sub.3 -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- Cl .sub.3 2 N(CH) J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCHF.sub.2 SCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- CH.sub.3 CH(OCH.sub.3).sub.2 J.sub.16 -- CH.sub.2 -- O -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.16 -- CH.sub.2 -- S -- H -- H CH.sub.3 -- -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.17 -- -- -- -- O H -- CH.sub.3 H -- -- -- -- Cl N(CH.sub.3).sub.2 J.sub.17 -- -- -- -- O H -- CH.sub.3 H -- -- -- -- CH.sub.3 CH(OCH.sub.3) .sub.2 J.sub.17 -- -- -- -- S H -- CH.sub.3 H -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- H H -- OCH.sub.3 NHCH.sub.3 J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- CH.sub.3 H -- Cl N(CH.sub.3).sub.2 J.sub.18 -- O -- -- -- H -- H H -- H CH.sub.3 -- CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- CH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.19 -- -- -- -- -- H -- CH.sub.3 CH.sub.3 -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.19 -- -- -- -- -- H -- H CH.sub.3 -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub .2 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 NHCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Br OCH.sub.3 N(CH.sub.3).sub.2 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- F OCH.sub.3 NHCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 NHCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 C.tbd.CH J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Cl Cl NHCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Br OCH.sub.3 NHCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 NHCH.sub. 3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 NHCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 OCH.sub.3 NHCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 148-151.5 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 191-193.5 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3
TABLE 2__________________________________________________________________________General Formula 2 m.p.J n L R.sub.1 R.sub.9 X Y (.degree.C.)__________________________________________________________________________J.sub.1 0 CH.sub.2 H CH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5J.sub.1 0 CH.sub.2 H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3J.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.2 FJ.sub.1 0 CH.sub.2 H CH.sub.3 OCH.sub.3 CF.sub.3J.sub.1 1 CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H C.sub.2 H.sub.5 OCH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H -n-C.sub.3 H.sub.7 OCH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H H OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H H OCH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H H CH.sub.3 CH.sub.3J.sub.1 0 O H H CH.sub.3 CH.sub.3J.sub.1 0 O H H CH.sub.3 OCH.sub. 3J.sub.1 0 O H H OCH.sub.3 OCH.sub.3J.sub.1 0 O H CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 O H CH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 O H CH.sub.3 CH.sub.3 CH.sub.3J.sub.1 0 O H C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.1 0 O H -n-C.sub.3 H.sub.7 OCH.sub.3 CH.sub.3J.sub.1 0 O H CH(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3J.sub.1 1 O H CH.sub.3 OCH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 5-F CH.sub.3 OCH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 6-Cl CH.sub.3 OCH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 6-Br CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 6-CH.sub.3 CH.sub. 3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 6-OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 O H CH.sub.3 OCH.sub.2 CF.sub.3 CH.sub.3J.sub.1 0 O H CH.sub.3 OCH.sub.3 CH(CH.sub.3)J.sub.1 0 O H CH.sub.3 OCH.sub.3 cyclopropylJ.sub.1 0 O H CH.sub.3 OCH.sub.3 C.tbd.CHJ.sub.1 0 O H CH.sub.3 OCH.sub.3 NH.sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 OCH.sub.2 CH.sub.2 FJ.sub.1 0 O H CH.sub.3 OCH.sub.3 SCH.sub.3J.sub.1 0 O H CH.sub.3 OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3J.sub.1 0 O H CH.sub.3 OCH.sub.3 OCH.sub.2 C.tbd.CHJ.sub.1 0 O H CH.sub.3 OCH.sub.3 CH(OCH.sub.3).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 1,3-dioxolan- 2-ylJ.sub.1 0 O H CH.sub.3 OCH.sub.3 2-methyl-1,3- dioxolan-2-ylJ.sub.1 0 O H CH.sub.3 OCH.sub.3 CH(OC.sub.2 H.sub.5).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 C(CH.sub.3)(OC.sub.2 H.sub.5).sub.2J.sub.1 0 O H CH.sub.3 OCH.sub.3 NHCH.sub.3J.sub.1 0 O H --CH.sub.2 CN OCH.sub.3 OCH.sub.3J.sub.1 0 O H --(CH.sub.2).sub.3 CN CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H OH CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --(CH.sub.2).sub.3 CH(CH.sub.3).sub.2 Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --CF.sub.2 H OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 CH.sub.2 Cl Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --(CH.sub.2).sub.5 Cl CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 OCH.sub.3 Cl OCH.sub.3J.sub.1 0 CH.sub.2 H --(CH.sub.2).sub.4 OCH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 CH.dbd.CH.sub.2 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 CH.dbd.CHCH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 C.tbd.CH OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --(CH.sub.2).sub.4 C.tbd.CH CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --OCH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --C.sub.6 H.sub.5 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H cyclopropyl OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H cyclohexyl OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H cyclopropylmethyl OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H cyclohexylmethyl CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --C(O)CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --C(O)(CH.sub.2).sub.5 H OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CO.sub.2 C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --(CH.sub.2).sub.4 H CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 C.sub. 6 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 --CH.dbd.CH--CH.sub.2 Cl CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 C.tbd.C--CH.sub.2 Cl CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH.sub.2 C(O)CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H --CH(CH.sub.3)CO.sub.2 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H H OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H H CH.sub.3 CH.sub.3J.sub.1 0 O H H CH.sub.3 CH.sub.3J.sub.1 0 O H H OCH.sub.3 CH.sub.3J.sub.1 0 O H H OCH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H -n-C.sub.4 H.sub.9 CH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 H -n-C.sub.4 H.sub.9 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 H -n-C.sub.4 H.sub.9 OCH.sub.3 OCH.sub.3J.sub.1 0 O H -n-C.sub.4 H.sub.9 CH.sub.3 CH.sub. 3J.sub.1 0 O H -n-C.sub.4 H.sub.9 OCH.sub.3 CH.sub.3J.sub.1 0 O H -n-C.sub.4 H.sub.9 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H -n-C.sub.3 H.sub.7 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J.sub.7 -- O H CH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 7-Cl CH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- O 7-Br CH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 6-F CH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- O 7-CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- O 7-OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 CH.sub.3 CH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5J.sub. 7 -- CH.sub.2 H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.2 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH.sub.2 FJ.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CF.sub.3J.sub.7 -- CH.sub.2 H H CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H C.sub.2 H.sub.5 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.2 CF.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 cyclopropylJ.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 NHCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH(OCH.sub.3).sub.2J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 1,3-dioxolan- 2-ylJ.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 CH(OC.sub.2 H.sub.5).sub.2J.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 --C.tbd.CHJ.sub.7 -- CH.sub.2 H CH.sub.3 OCH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2J.sub.7 -- CH.sub.2 H OH OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H (CH.sub.2).sub.2 CH(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH.sub.2 Cl OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H (CH.sub.2).sub.5 Cl CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH.dbd.CH.sub.2 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH.dbd.CHCH.sub.2 Cl CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH.dbd.CHCH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub. 2 C.tbd.CCH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H OCH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H O(CH.sub.2).sub.4 CH.sub.3 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H C.sub.6 H.sub.5 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H cyclopropyl CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H cyclopentyl OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H COCH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH.sub.2 CH.dbd.CHCl CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 H CH(CH.sub.3)CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 2a General Formula 2a J n L Q Q.sub.1 Q.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 R.sub.7 R.sub.8 X Y m.p.(.degree.C.) J.sub.2 0 CH.sub.2 -- -- -- H -- H CH.sub.3 -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH.sub.2 F J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CF.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H H -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H C.sub.2 H.sub.5 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H -n-C.sub.3 H.sub.7 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH(CH.sub.3).sub.2 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.2 1 O -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 O -- -- -- H C.sub.2 H.sub.5 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- 6-Br CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- 6-Cl CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- 5-F CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 O -- -- -- 6-CH.sub.3 CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.2 0 O -- -- -- 6-OCH.sub.3 CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 OCH.sub.3 175- 183,d J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 CH.sub.2 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.2 F J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 CF.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H -- H CH.sub.3 -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.3 0 O -- -- -- H -- H H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- 5-F -- H H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- 6-Cl -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- 6-Br -- H H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.3 0 O -- -- -- 5-CH.sub.3 -- H H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.3 0 O -- -- -- 6-OCH.sub.3 -- H H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.3 1 O -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.3 1 CH.sub.2 -- -- -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.3 1 O -- -- -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.3 1 O -- -- -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.3 1 O -- -- -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.4 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.4 1 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 J.sub.4 0 0 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.4 1 0 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 CH.sub.3 J.sub.5 1 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.5 0 -- -- -- -- H H -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.6 0 -- -- -- -- H H -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.6 1 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- CH.sub.3 -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.2 F J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CF.sub.3 J.sub.8 -- O -- -- -- H -- H -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.8 -- O -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- 7-Cl -- H -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.9 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.9 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.9 -- O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.10 -- -- -- -- -- H C.sub.2 H.sub. 5 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.11 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.11 -- -- -- -- -- H C.sub.2 H.sub.5 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- --OCH.sub.3 OCH.sub.3 J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.12 -- CH.sub.2 -- -- -- H -- CH.sub.3 -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.12 -- O -- -- -- H -- CH.sub.3 -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.13 -- CH.sub.2 O -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.13 -- CH.sub.2 O -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.13 -- O O -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.13 -- O O -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.13 -- O CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.13 -- O CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.14 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.14 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- O -- H -- H H CH.sub.3 -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- O -- H -- H H CH.sub.3 -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- O -- H -- H H C.sub.2 H.sub.5 -- -- -- OCH.sub.3 CF.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 CH.sub.3 H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.2 F J.sub.15 -- -- -- O -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CF.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- S -- H -- H CH.sub.3 CH.sub.3 -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- H H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub. 3 OCH.sub.3 192-194 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.3 186-187 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- CH.sub.3 OC.sub.2 H.sub.5 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CH.sub.2 F J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 CF.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 CH.sub.3 H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 C.sub.2 H.sub.5 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 OC.sub.2 H.sub. 5 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.2 F J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CF.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H CH.sub.3 -- -- -- OCH.sub.3 CH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H CH.sub.3 -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- 6-Cl -- CH.sub.3 H H -- -- -- CH.sub.3 CH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- 6-Cl -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- 6-Cl -- CH.sub.3 H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- 5-Br -- H H CH.sub.3 -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- 6-F -- CH.sub.3 H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- 5-CH.sub.3 -- CH.sub.3 H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- O -- 6-OCH.sub.3 -- CH.sub.3 H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- 6-Cl -- CH.sub.3 H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.15 -- -- -- S -- 6-Cl -- CH.sub.3 H H -- -- -- CH.sub.3 OCH.sub.3 J.sub.16 -- CH.sub.2 -- O -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.16 -- CH.sub.2 -- S -- H -- H CH.sub.3 -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- CH.sub.3 CH.sub.3 J.sub.17 -- -- -- -- O H -- CH.sub.3 H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.17 -- -- -- -- S H -- CH.sub.3 H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.17 -- -- -- -- O H -- CH.sub.3 CH.sub.3 -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.17 -- -- -- -- O H -- H H -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- H H -- CH.sub.3 OCH.sub.3 J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- CH.sub.3 H -- OCH.sub.3 CH.sub.3 J.sub.18 -- O -- -- -- H -- H H -- H CH.sub.3 -- CH.sub.3 OCH.sub.3 J.sub.19 -- -- -- -- -- H -- CH.sub.3 CH.sub.3 -- -- -- -- CH.sub.3 OCH.sub.3 J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.19 -- -- -- -- -- H -- CH.sub.3 CH.sub.3 -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 J.sub.20 -- CH.sub.2 -- -- -- 7-Cl -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3 J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- F OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Br OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 OCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SCH.sub.3 OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 122-122.5 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 CF.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl CH.sub.3 OC.sub.2 H.sub.5 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 C.sub.2 H.sub.5 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- F OCH.sub.3 CH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 CH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Br OCH.sub.3 CH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 CH.sub. 3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SCH.sub.3 OCH.sub.3 CH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 187-190 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 CF.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(CH.sub.3).sub.2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.2 CF.sub.3 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 cyclopropyl J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 N(CH.sub.3).sub. 2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 1,3-dioxolan- 2-yl J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub. 3 CH(OC.sub.2 H.sub.5).sub.2 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCF.sub.2 H OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 cyclopropyl J.sub.3 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.3 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.3 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.3 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 1,3-dioxolan- 2-yl J.sub.3 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.2 C.tbd.CH J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 J.sub.4 0 CH.sub. 2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 cyclopropyl J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.4 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(CH.sub.3).sub.2 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 cyclopropyl J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 C.tbd.CH J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 1,3-dioxolan - 2-yl J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(CH.sub.3).sub.2 J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 cyclopropyl J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.6 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 C.tbd.CH J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 1,3-dioxolan- 2-yl J.sub.8 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 cyclopropyl J.sub.9 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.9 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.9 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 CH(OCH.sub.3).sub.2 J.sub.11 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.11 -- -- -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.12 -- O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 NHCH.sub.3 J.sub.12 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.12 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 1,3-dioxolan- 2-yl J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 SCH.sub.3 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.tbd.CH J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.2 CF.sub.3 OCH.sub.3 J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.15 -- -- -- O -- H -- H H H -- -- -- OCH.sub.3 C.tbd.CH J.sub.15 -- -- -- O -- H -- H H H -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd. CHCl J.sub.15 -- -- -- O -- H -- H H H -- -- -- CH.sub.3 NHCH.sub.3 J.sub.15 -- -- -- O -- H -- H H CH.sub.3 -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.15 -- -- -- O -- H -- H H CH.sub.3 -- -- -- OCH.sub.3 cyclopropyl J.sub.15 -- -- -- O -- H -- H H CH.sub.3 -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.15 -- -- -- O -- H -- CH.sub.3 CH.sub.3 H -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.15 -- -- -- O -- H -- CH.sub.3 CH.sub.3 H -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- OCH.sub. 3 OCH.sub.2 C.tbd.CH J.sub.15 -- -- -- O -- H -- CH.sub.3 CH.sub.3 H -- -- -- OCH.sub.3 SCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 cyclopropyl J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 N(CH.sub.3).s ub.2 J.sub.15 -- -- -- S -- H -- CH.sub.3 CH.sub.3 CH.sub.3 -- -- -- OCH.sub.3 CH(CH.sub.3).sub.2 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- CH.sub.3 CH(OCH.sub.3).sub.2 J.sub.16 -- CH.sub.2 -- O -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub. 16 -- CH.sub.2 -- S -- H -- H CH.sub.3 -- -- -- -- OCH.sub.3 OCH.sub.2 CH.dbd.CH.sub.2 J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.17 -- -- -- -- O H -- CH.sub.3 H -- -- -- -- OCH.sub.3 N(CH.sub.3). sub.2 J.sub.17 -- -- -- -- O H -- CH.sub.3 H -- -- -- -- CH.sub.3 CH(OCH.sub.3).sub.2 J.sub.17 -- -- -- -- S H -- CH.sub.3 H -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- H H -- OCH.sub.3 NHCH.sub.3 J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- CH.sub.3 H -- OCH.sub.3 N(CH.sub.3).sub.2 J.sub.18 -- O -- -- -- H -- H H -- H CH.sub.3 -- CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- CH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.19 -- -- -- -- -- H -- CH.sub.3 CH.sub.3 -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub.19 -- -- -- -- -- H -- H CH.sub.3 -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 NHCH.sub.3 J.sub. 20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 C.tbd.CH J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- OCH.sub.3 CH(OCH.sub.3).sub.2 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 NHCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Br OCH.sub.3 N(CH.sub.3).sub.2 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- F OCH.sub.3 NHCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 NHCH.sub.3 J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 C.tbd.CH J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 OCH.sub.2 CH.sub.2 F J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Cl OCH.sub.3 NHCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Br OCH.sub.3 NHCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OCH.sub.3 OCH.sub.3 NHCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 NHCH.sub.3 J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 OCH.sub.3 NHCH.sub.3
TABLE 3__________________________________________________________________________General Formula 3 m.p.J n L Q Q.sub.1 Q.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 R.sub.7 R.sub.8 R.sub.9 X.sub.1 Y.sub.1 (.degree.C.)__________________________________________________________________________J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 OJ.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 OJ.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 CH.sub.2J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OC.sub.2 H.sub.5 OJ.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCF.sub.2 H OJ.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 CH.sub.2J.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 OJ.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCF.sub.2 H OJ.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 OJ.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCF.sub.2 H OJ.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 OJ.sub.2 1 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 OJ.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3 OJ.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCF.sub.2 H OJ.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 OJ.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OC.sub.2 H.sub.5 OJ.sub.3 1 O -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 OJ.sub.4 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.4 0 O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.4 1 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 OJ.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 OJ.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 CH.sub.2J.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 CH.sub.3 OJ.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3 OJ.sub.8 -- O -- -- -- H -- H -- -- -- -- -- -- CH.sub.3 OJ.sub.9 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.11 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3 OJ.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- CH.sub.3 OJ.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.13 -- CH.sub.2 O -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.13 -- O O -- -- H -- -- -- -- -- -- -- -- CH.sub.3 OJ.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 0J.sub.14 -- O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.15 -- -- -- O -- H -- CH.sub. 3 H H -- -- -- -- OCH.sub.3 OJ.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 CH.sub.2J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3 OJ.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 OJ.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3 OJ.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 OJ.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 CH.sub.2J.sub.16 -- CH.sub.2 -- O -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.16 -- CH.sub.2 -- S -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3 OJ.sub.16 -- CH.sub.2 -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3 OJ.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- CH.sub.3 OJ.sub.17 -- -- -- -- O H -- H H -- -- -- -- -- OCH.sub.3 OJ.sub.17 -- -- -- -- S H -- H H -- -- -- -- -- OCH.sub.3 OJ.sub.18 -- CH.sub.2 -- -- -- H -- H H -- H H -- -- OCH.sub.3 OJ.sub.18 -- CH.sub.2 -- -- -- H -- H H -- CH.sub.3 H -- -- CH.sub.3 OJ.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 OJ.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- CH.sub.3 OJ.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 OJ.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 CH.sub.2J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 OJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl -- OCH.sub.3 OJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- F -- OCH.sub.3 OJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Br -- OCH.sub.3 OJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- OCH.sub.3 OJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- OCH.sub.3 CH.sub.2J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- OCH.sub.3 CH.sub.2J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- OCH.sub.3 CH.sub.2J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Cl -- OCH.sub.3 OJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- F -- OCH.sub.3 OJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Br -- OCH.sub.3 OJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- OCH.sub.3 OJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- OCH.sub.3 OJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- OCH.sub.3 OJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- OCH.sub.3 O__________________________________________________________________________
TABLE 4__________________________________________________________________________General Formula 4 m.p.J n L Q Q.sub.1 Q.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 R.sub.7 R.sub.8 R.sub.9 X.sub.1 (.degree.C.)__________________________________________________________________________J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OC.sub.2 H.sub.5J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCF.sub.2 HJ.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3J.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCF.sub.2 HJ.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OC.sub.2 H.sub.5J.sub.2 1 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OC.sub.2 H.sub.5J.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3J.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3J.sub.3 1 O -- -- -- H -- H H -- -- -- -- -- OCH.sub.3J.sub.4 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.4 0 O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.4 1 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OC.sub.2 H.sub.5J.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCF.sub.2 HJ.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3J.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3J.sub.8 -- O -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3J.sub.9 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.11 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OC.sub.2 H.sub.5J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- CH.sub.3J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- OCF.sub.2 HJ.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- CH.sub.3J.sub.13 -- CH.sub.2 O -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.13 -- O O -- -- H -- -- -- -- -- -- -- -- OC.sub.2 H.sub.5J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- -- CH.sub.3J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3J.sub.14 -- O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- OCHF.sub.2J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3J.sub.16 -- CH.sub.2 -- O -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3J.sub.16 -- CH.sub.2 -- S -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3J.sub.16 -- CH.sub.2 -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3J.sub.17 -- -- -- -- O H -- H H -- -- -- -- -- OCH.sub.3J.sub.17 -- -- -- -- S H -- H H -- -- -- -- -- OCH.sub.3J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- CH.sub.3 H -- -- CH.sub.3J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- H H -- -- OCH.sub.3J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- OCH.sub.3J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- OC.sub.2 H.sub.5J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OC.sub.2 H.sub.5J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- OC.sub.2 H.sub.5J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- F -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Br -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Cl -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- F -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Br -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- OCH.sub.3__________________________________________________________________________
TABLE 5__________________________________________________________________________General Formula 5 m.p.J n L Q Q.sub.1 Q.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 R.sub.7 R.sub.8 R.sub.9 X.sub.1 Y.sub.3 (.degree.C.)__________________________________________________________________________J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 CH.sub.3J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 HJ.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 CH.sub.3J.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 CH.sub.3J.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3 HJ.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 CH.sub.3J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OC.sub.2 H.sub.5 HJ.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 HJ.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.2 1 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 HJ.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3 HJ.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3 HJ.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 HJ.sub.3 1 O -- -- -- H -- H H -- -- -- -- -- CH.sub.3 HJ.sub.4 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.4 0 O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3J.sub.4 1 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OC.sub.2 H.sub.5 CH.sub.3J.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 CH.sub.3J.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3 HJ.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3 HJ.sub.8 -- O -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3 CH.sub.3J.sub.9 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 HJ.sub.11 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3 HJ.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- CH.sub.3 HJ.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3 HJ.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- CH.sub.3 HJ.sub.13 -- CH.sub.2 O -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.13 -- O O -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 HJ.sub. 14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 HJ.sub.14 -- O -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 CH.sub.3J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 HJ.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 HJ.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 CH.sub.3J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 HJ.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3 CH.sub.3J.sub.16 -- CH.sub.2 -- O -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3 HJ.sub.16 -- CH.sub.2 -- S -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3 HJ.sub.16 -- CH.sub.2 -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3 HJ.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3 HJ.sub.17 -- -- -- -- O H -- H H -- -- -- -- -- OCH.sub.3 CH.sub.3J.sub.17 -- -- -- -- S H -- H H -- -- -- -- -- CH.sub.3 HJ.sub.18 -- CH.sub.2 -- -- -- H -- H H -- H H -- -- OCH.sub.3 HJ.sub.18 -- CH.sub.2 -- -- -- H -- H H -- CH.sub.3 H -- -- OCH.sub.3 HJ.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 HJ.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- OCH.sub.3 HJ.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 HJ.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3 CH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl -- CH.sub.3 HJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- F -- OCH.sub.3 HJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Br -- OCH.sub.3 HJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- OCH.sub.3 HJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- OCH.sub.3 HJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- OCH.sub.3 HJ.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- OCH.sub.3 HJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Cl -- OCH.sub.3 HJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- F -- OCH.sub.3 HJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Br -- OCH.sub.3 HJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- OCH.sub.3 HJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- OCH.sub.3 HJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- OCH.sub.3 HJ.sub.21 -- O -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- OCH.sub.3 H__________________________________________________________________________
TABLE 6__________________________________________________________________________General Formula 6 7 m.p.J n L Q Q.sub.1 Q.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 R.sub.7 R.sub.8 R.sub.9 X.sub.2 Y.sub.2 (.degree.C.)__________________________________________________________________________J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 C.sub.2 H.sub.5 OC.sub.2 H.sub.5J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.2 CF.sub.3 SCH.sub.3J.sub.1 0 CH.sub. 2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3 SC.sub.2 H.sub.5J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 C.sub.2 H.sub.5 OCF.sub.2 HJ.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 C.sub.2 H.sub.5 SCF.sub.2 HJ.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 C.sub.2 H.sub.5 OCH.sub.3J.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 C.sub.2 H.sub.5 SCH.sub.3J.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 C.sub.2 H.sub.5 SCF.sub.2 HJ.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.2 CF.sub.3 SCH.sub.3J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.2 CH.sub.3 SC.sub.2 H.sub.5J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.2 CH.sub.3 SC.sub.2 H.sub.5J.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.2 CH.sub.3 SCH.sub.3J.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.2 CF.sub.3 SC.sub.2 H.sub.5J.sub.2 1 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- C.sub.2 H.sub.5 SCH.sub.3J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.3 1 O -- -- -- H -- H H -- -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.4 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.4 0 O -- -- -- H -- -- -- -- -- -- -- -- C.sub.2 H.sub.5 SCH.sub.3J.sub.4 1 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.5 0 0 0 0 0 H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- C.sub.2 H.sub.5 SCH.sub.3J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.2 CF.sub.3 SCH.sub.3J.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 CH.sub.2 CH.sub.3 SC.sub.2 H.sub.5J.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 CH.sub.3 SC.sub.2 H.sub.5J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.8 -- O -- -- -- H -- H -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.9 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- C.sub.2 H.sub.5 SC.sub.2 H.sub.5J.sub.11 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- C.sub.2 H.sub.5 SCH.sub.3J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- C.sub.2 H.sub.5 SCH.sub.3J.sub.13 -- CH.sub. 2 O -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.13 -- O O -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.14 -- O -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3 SCH.sub.3J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- C.sub.2 H.sub.5 SCH.sub.3J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3 SCH.sub.3J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3 SCH.sub.3J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.16 -- CH.sub.2 -- O -- H -- CH.sub.3 H -- -- -- -- -- C.sub.2 H.sub.5 SCH.sub.3J.sub.16 -- CH.sub.2 -- S -- H -- CH.sub.3 H -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.16 -- CH.sub.2 -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.17 -- -- -- -- O H -- H H -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.17 -- -- -- -- S H -- H H -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub. 18 -- CH.sub.2 -- -- -- H -- H H -- H H -- -- CH.sub.3 SCH.sub.3J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- CH.sub.3 H -- -- CH.sub.3 SCH.sub.3J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SC.sub.2 H.sub.5J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3 SCH.sub.3J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- C.sub.2 H.sub.5 SCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl -- CH.sub.3 SCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- F -- CH.sub.3 SCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Br -- CH.sub.3 SCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- CH.sub.3 SCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- CH.sub.3 SCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- CH.sub.3 SCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- CH.sub.3 SCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Cl -- CH.sub.3 SCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- F -- CH.sub.3 SCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Br -- CH.sub.3 SCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- CH.sub.3 SCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- CH.sub.3 SCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- CH.sub.3 SCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- CH.sub.3 SCH.sub.3__________________________________________________________________________
TABLE 7__________________________________________________________________________General Formula 7J n L Q Q.sub.1 Q.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 R.sub.7 R.sub.8 R.sub.9 X.sub.3 m.p. (.degree.C.)__________________________________________________________________________J 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 OCH.sub.3J.sub.1 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.1 0 O -- -- -- H -- -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.2 0 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.2 0 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.2 1 CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.2 1 O -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- CH.sub.3J.sub.3 0 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3J.sub.3 1 CH.sub.2 -- -- -- H -- H H -- -- -- -- -- OCH.sub.3J.sub.3 1 O -- -- -- H -- H H -- -- -- -- -- OCH.sub.3J.sub.4 0 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3J.sub.4 0 O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.4 1 CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.5 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.6 0 -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 CH.sub.3J.sub.7 -- CH.sub.2 -- -- -- H CH.sub.3 -- -- -- -- -- -- CH.sub.3 OCH.sub.3J.sub.8 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- CH.sub.3J.sub.8 -- O -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3J.sub.9 -- CH.sub. 2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.10 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- OCH.sub.3J.sub.11 -- -- -- -- -- H CH.sub.3 -- -- -- -- -- -- -- CH.sub.3J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3J.sub.12 -- CH.sub.2 -- -- -- H -- H -- -- -- -- -- -- CH.sub.3J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- OCH.sub.3J.sub.12 -- O -- -- -- H -- H -- -- -- -- -- -- CH.sub.3J.sub.13 -- CH.sub.2 O -- -- H -- -- -- -- -- -- -- -- CH.sub.3J.sub.13 -- O O -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.13 -- CH.sub.2 CH.sub.2 -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3J.sub.14 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.14 -- O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3J.sub.15 -- -- -- O -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3J.sub.15 -- -- -- S -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- CH.sub.3J.sub.15 -- -- -- SO.sub.2 -- H -- CH.sub.3 H H -- -- -- -- OCH.sub.3J.sub.16 -- CH.sub.2 -- O -- H -- CH.sub.3 H -- -- -- -- -- CH.sub.3J.sub.16 -- CH.sub.2 -- S -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3J.sub.16 -- CH.sub.2 -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- CH.sub.3J.sub.16 -- O -- SO.sub.2 -- H -- CH.sub.3 H -- -- -- -- -- OCH.sub.3J.sub.17 -- -- -- -- O H -- H H -- -- -- -- -- CH.sub.3J.sub.17 -- -- -- -- S H -- H H -- -- -- -- -- CH.sub.3J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- H H -- -- OCH.sub.3J.sub.18 -- CH.sub.2 -- -- -- H -- H H -- CH.sub.3 H -- -- CH.sub.3J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- OCH.sub.3J.sub.19 -- -- -- -- -- H -- H H -- -- -- -- -- CH.sub.3J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.20 -- CH.sub.2 -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- OCH.sub.3J.sub.20 -- O -- -- -- H -- -- -- -- -- -- -- -- CH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Cl -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- F -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- Br -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- OCH.sub.3J.sub.21 -- CH.sub.2 -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Cl -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- F -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- Br -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- OSO.sub.2 CH.sub.3 -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- SO.sub.2 N(CH.sub.3).sub.2 -- OCH.sub.3J.sub.21 -- O -- -- -- -- -- -- -- -- -- -- CO.sub.2 CH.sub.3 -- OCH.sub.3__________________________________________________________________________
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 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
TABLE 8______________________________________ Active Weight Percent* Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 3-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 0.1-95 5-99.9 0-15High Strength 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., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "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.
The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.
For further information regarding the art of formulation, see for example:
H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;
R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;
H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;
G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and
J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
In the following examples, all parts are by weight unless otherwise indicated.
EXAMPLE 9
Wettable Powder
______________________________________N--[4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-bonyl]-2-methyl-benzo[B]thiophene-7-methanesulfon-amide-1,1-dioxide 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 10
Wettable Powder
______________________________________N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-benzo[B]thiophene-7-methanesulfon-amide-1,1-dioxide 50%sodium alkylnaphthalenesulfonate 2%low viscosity methyl cellulose 2%diatomaceous earth 46%______________________________________
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.
EXAMPLE 11
Granule
______________________________________Wettable Powder of Example 10 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 12
Extruded Pellet
______________________________________1,3-dihydro-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]-1-oxo-benzo[c]furan-7-methanesulfon-amide 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.
EXAMPLE 13
Low Strength Granule
______________________________________1,3-dihydro-N--[(4,6-dimethoxypyrimidin-2-yl)amino--carbonyl]-1-oxo-benzo[c]furan-7-methanesulfon-amide 0.1%attapulgite granules 99.9%(U.S.S. 20-40 mesh)______________________________________
The active ingredient is dissolved in a solvent and the solution is sprayed when 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 14
Granule
______________________________________1,3-dihydro-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]-1-oxo-benzo[c]furan-7-methanesulfon-amide 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 15
Low Strength Granule
______________________________________1,3-dihydro-N--[(4,6-dimethoxypyrimidin-2-yl)amino-carbonyl]-1-oxo-benzo[c]furan-7-methanesulfon-amide 1%N,N--dimethylformamide 9%attapulgite granules 90%(U.S.S. 20-40 sieve)______________________________________
The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
EXAMPLE 16
Aqueous Suspension
______________________________________N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-bonyl]-2-methyl-benzo[B]thiophene-7-methanesulfon-amide-1,1-dioxide 40%polyacrylic acid thickener 0.3%dodecylphenol polyethylene glycol 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 17
Solution
______________________________________N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-benzo[B]thiophene-7-methanesulfon-amide-1,1-dioxide, sodium salt 5%water 95%______________________________________
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
EXAMPLE 18
High Strength Concentrate
______________________________________1,3-dihydro-N--[(4,6-dimethoxypyrimidin-2-yl)amino-carbonyl]-1-oxo-benzo[c]furan-7-methanesulfon-amide 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 19
Wettable Powder
______________________________________N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-benzo[B]thiophene-7-methanesulfon-amide-1,1-dioxide 90%dioctyl sodium sulfosuccinate 0.1%synthetic fine silica 9.9%______________________________________
The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.
EXAMPLE 20
Wettable Powder
______________________________________1,3-dihydro-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]-1-oxo-benzo[c]furan-7-methanesulfon-amide 40%sodium ligninsulfonate 20%montmorillonite clay 40%______________________________________
The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.
EXAMPLE 21
Oil Suspension
______________________________________N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-bonyl]-2-methyl-benzo[B]thiophene-7-methanesulfon-amide-1,1-dioxide 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 22
Dust
______________________________________N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-bonyl]-2-methyl-benzo[B]thiophene-7-methanesulfon-amide-1,1-dioxide 10%attapulgite 10%Pyrophyllite 80%______________________________________
The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.
EXAMPLE 23
Oil Suspension
______________________________________N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-benzo[B]thiophene-7-methanesul-fonamide-1,1-dioxide 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 24
Wettable Powder
______________________________________1,3-dihydro-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]-1-oxo-benzo[c]furan-7-methanesulfon-amide 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.
Utility
The compounds of the present invention are active herbicides, having 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, billboards, and highway and railroad structures.
The rates of application for the compounds of the invention are determined by a number of factors, including 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 0.05 to 5 kg/ha. the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, of for situations where only short-term persistance 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 compounds may also be used in combination with mefluidide.
The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedure and results follow.
Test A
Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea sp.), cocklebur (Xanthum sp.), sorghum, corn, soybean, cotton rice, sugar beet, rice, wheat and purple nutsedge (Cyperus rotundus) tubers were planted in a growth medium and treated pre-emergence with the test compounds dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foilage 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 of necrosis;
G=growth retardation; and
H=formative effects.
The test compounds are referenced in the table of results as follows:
______________________________________Compounds______________________________________Compound 1 ##STR38##Compound 2 ##STR39##Compound 3 ##STR40##Compound 4 ##STR41##Compound 5 ##STR42##Compound 6 ##STR43##Compound 7 ##STR44##Compound 8 ##STR45##Compound 9 ##STR46##Compound 10 ##STR47##Compound 11 ##STR48##Compound 12 ##STR49##______________________________________
TABLE A______________________________________ Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POST-EMERGENCEMorningglory 6C,9G 3C,9G 3C,6H 10CCocklebur 5C,8G 5C,9G 3C,5G 10CSicklepod 4C,8G 3C,3H 2C,3G 9CNutsedge 3C,8G 2G 2C,3G 5GCrabgrass 0 0 2C,5G 3C,8GBarnyardgrass 0 0 3C,6H 4C,9HWild Oats 0 0 3C,6G 3C,8GWheat 0 0 3C,8G 6GCorn 3C,9H 1H 3C,9G 2U,9GSoybean 3C,9G 2C,8G 3H 9CRice 2C,6G 2G 5C,9G 6C,9GSorghum 3C,9H 2C,9H 4C,9H 6C,9HSugar beet 9C 4C,9G 3C,4H 10CCotton 3C,8H 3C,5G 0 9C______________________________________PRE-EMERGENCEMorningglory 8G 2C,3H 0 9GCocklebur 2C,5H 2C,2H -- 8HSicklepod 1C,2G 0 0 2C,7GNutsedge 2G 0 0 4GCrabgrass 1C 0 2G 2C,5GBarnyardgrass 0 0 1H 4C,9HWild Oats 0 0 2C,7G 2C,8HWheat 4G 3G 2C,8G 3C,9HCorn 2C,8H 0 3C,7H 2U,9GSoybean 2C,8H 0 0 3C,8HRice 2C,7G 2G 3C,8H 5C,9HSorghum 3C,8H 3C,8H 3C,9G 5C,9HSugar beet 9C 3C,8G 0 9CCotton 8H 1C 0 9G______________________________________ Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. 8Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POST-EMERGENCEMorningglory 8G 10C 2C,6G 10CCocklebur 5G 3C,9G 3G 10CNutsedge 2C,3G 3G 0 3GCrabgrass 3C,7G 3G 0 5GBarnyardgrass 9C 3C,6H 3C,8H 3C,8HWild Oats 9C 2C,4G 4C,8G 2CWheat 10C 3G 9C 9GCorn 9C 4C,9H 4C,9G 3C,9HSoybean 5C,9H 5C,9G 3C,8H 9CRice 9C 9C 9C 9CSorghum 9C 5C,9H 5C,9G 5C,9HSugar beet 3C,7H 9C 3C,7G 5C,9GCotton 3C,7H 5C,9G 3C,5G 5C,9GSicklepod 3C,3H 4C,7H 2C,5G 9C______________________________________PRE-EMERGENCEMorningglory 3C,5H 9G 8G 9GCocklebur 0 5H 2H 8HNutsedge 0 0 2C 3GCrabgrass 0 0 0 2C,5GBarnyardgrass 3C,5G 0 1H 2C,6GWild Oats 8G 2C,3G 5G 2C,5GWheat 2C,8H 2G 2C,9H 2C,7GCorn 3C,8H 3C,3G 2C,8H 4C,9HSoybean 1C 3C,5H 2C,2H 4C,6HRice 5C,9H 7H 5C,9H 5C,9HSorghum 4C,9H 3C,7H 5C,9H 4C,9GSugar beet 8G 9C 5G 9CCotton 2G 5G 5G 3C,7GSicklepod 2C 2C,2H 1C 2C,4G______________________________________ Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POST-EMERGENCEMorningglory 3C,9G 3G 9C 10CCocklebur 2G 3G 2C 5C,9GNutsedge 5G 0 2C,7G 2C,6GCrabgrass 0 0 2G 2CBarnyardgrass 0 0 0 0Wild Oats 0 0 0 0Wheat 0 0 0 0Corn 0 0 1H 3C,8HSoybean 5C,9G 3C,8G 5C,9G 5C,9GRice 0 0 0 0Sorghum 0 0 3G 3C,8HSugar beet 3C,6G 0 5C,9G 5C,9GCotton 9C 2G 4C,9G 4C,9GSicklepod 2C,3G 1C 3C,8G 4C,6G______________________________________PRE-EMERGENCEMorningglory 8G 3G 9G 9GCocklebur 2H 3G -- 8HNutsedge 3G 0 5G 0Crabgrass 4G 3G 0 0Barnyardgrass 0 0 3G 3GWild Oats 0 0 3G 5GWheat 0 0 4G 8GCorn 0 3G 2C,7G 9GSoybean 1H 0 2H 3C,7GRice 0 0 2G 2GSorghum 0 2G 5G 9GSugar beet 5G 2G 5C,9G 5C,9GCotton 2G 0 8G 8GSicklepod 5G 4G 2C,7G 2C______________________________________
Test B
Postemergence
Two round pans (25 cm diameter by 12.5 cm deep) were filled with Woodstown sandy loam soil. One pan was planted with blackgrass (Alpecurus myosuroides), sugar beets, nutsedge (Cyperus rotundus) tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa), jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), oil seed rape (Brassica napus), and giant foxtail (Seraria faberii). The other pan was planted with wheat, cotton, rice, corn, soybean, wild oats (Avena fatua), cocklebur (Xantium pensylvanicum), morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense) and barnyardgrass (Echinochloa crusgalli). The plants were grown for approximately fourteen days, then sprayed post-emergence with the chemicals dissolved in a non-phytotoxic solvent.
Preemergence
Two round pans (25 cm diameter by 12.5 cm deep) were filled with Woodstown sandy loam soil. One pan was planted with blackgrass, sugar beets, nutsedge, crabgrass, sicklepod, teaweed, jimsonweed, velvetleaf, oil seed rape, and giant foxtail. The other pan was planted with wheat, cotton, rice, corn, soybeans, wild oats, cocklebur, morningglory, johnsongrass, and barnyardgrass. The two pans were sprayed pre-emergence with the chemicals dissolved in a non-phytotoxic solvent.
Treated plants and controls were maintained in the greenhouse for 28 days, then all treated plants were compared to controls and visually rated for plant response utilizing the rating system as described for Test A.
Response ratings are contained in Table B. The data show the potential utility of several of the compounds tested for selective weed control in crops such as wheat, soybeans and cotton.
TABLE B______________________________________PRE-EMERGENCE ONWOODSTOWN SANDY LOAM______________________________________Compound 1POST-EMERGENCERate g/ha 62 16 4______________________________________Corn 3G 0 0Wheat 0 0 0Rice 5G 3G 0Soybean 9G 6G 3GCotton 7G 3G 0Sugar beet 7G 3G 0Rape -- -- --Crabgrass 0 0 0Johnsongrass 9G 4G 0Blackgrass 0 0 0Barnyardgrass 3G 0 0Nutsedge 5G 2G 0Giant Foxtail 6G 0 0Wild Oats 0 0 0Cocklebur 8G 3G 0Morningglory 9G 8G 3GTeaweed 0 0 0Sicklepod 3G 0 0Jimsonweed 8G 6G 2GVelvetleaf 9G 7G 3G______________________________________PRE-EMERGENCERate g/ha 250 62______________________________________Corn 2G 0Wheat 0 0Rice 7G 4GSoybean 3G 0Cotton 7G 2GSugar beet 9G 3GRape -- --Crabgrass 9G 5GJohnsongrass 8G 4GBlackgrass 8G 3GBarnyardgrass 4G 2GNutsedge 8G 5GGiant Foxtail 6G 2GWild Oats 0 0Cocklebur 8G 0Morningglory 0 0Teaweed 9G 5GSicklepod 10G 6GJimsonweed 8G 6GVelvetleaf 8G 4G______________________________________Compound 2POST-EMERGENCERate g/ha 62 16 4______________________________________Corn 0 0 0Wheat 0 0 0Rice 6G 4G 0Soybean 9G 8G 5GCotton 5G 3G 0Sugar beet 9G 5G 0Rape -- -- --Crabgrass 3G 0 0Johnsongrass 5G 2G 0Blackgrass 0 0 0Barnyardgrass 3G 0 0Nutsedge 7G 3G 0 -Giant foxtail 7G 4G 0Wild Oats 0 0 0Cocklebur 9G 5G 2GMorningglory 9G 6G 3GTeaweed 4G 0 0Sicklepod 6G 3G 0Jimsonweed 8G 4G 2GVelvetleaf 9G 5G 0______________________________________PRE-EMERGENCERate g/ha 250 62 16______________________________________Corn 0 0 0Wheat 2G 0 0Rice 7G 6G 6GSoybean 2C 0 0Cotton 0 0 0Sugar beet 10G 8G 0Rape -- -- --Crabgrass 9G 8G 6GJohnsongrass 8G 5G 0Blackgrass 8G 4G 0Barnyardgrass 3G 0 0Nutsedge 8G 5G 2GGiant Foxtail 4G 2G 0Wild Oats 0 0 0Cocklebur 3G 0 0Morningglory 3G 0 0Teaweed 9G 5G 0Sicklepod 8G 8G 5GJimsonweed 9G 6G 0Velvetleaf 8G 3G 0______________________________________Compound 4.sup.1POST-EMERGENCERate g/ha 62 16 4 1______________________________________Corn 100.70 100.60 90.30 80Wheat 0.0 0.0 0.0 0.0Rice 80.0 70.0 30.0 0.0Soybean 100.90 100.90 100.80 70.20Cotton 100.50 100.20 40.0 0.0Sugar beet 100.90 40.90 0.40 0.0Rape 100.100 100.90 100.90 50.40Crabgrass 20.0 0.0 0.0 0.0Johnsongrass 100.90 100.0 60.0 20Blackgrass 100.70 70.0 30.0 0.0Barnyardgrass 70.50 40.0 0.0Nutsedge 40.-- 30.0 0.0 0.0Giant Foxtail 50.0 0.0 0.0 0.0Wild Oats 30.0 0.0 0.0 0.0Cocklebur 100.90 60.70 30.0 0.0Morningglory 100.90 40.90 0.90 0.50Teaweed 80.80 50.80 30.0 0.0Sicklepod 100.100 90.90 30.70 0.0Jimsonweed 100.90 90.90 60.70 30.30Velvetleaf 100.100 100.90 100.90 1______________________________________PRE-EMERGENCERate g/ha 250 62 16______________________________________Corn 90.100 40.30 0.0Wheat 30.30 0.0 0.0Rice 100 90.100 40.60Soybean 80.100 60.50 20.0Cotton 40.60 0.50 0.0Sugar beet 90.100 30.100 0.50Rape 100 80.50 30.0Crabgrass 90.60 0.30 0.0Johnsongrass 90.100 90.90 80.60Blackgrass 90.100 70.80 0.40Barnyardgrass 90.100 70.60 20.20Nutsedge 0.0 0.0 0.0Giant Foxtail 100 70.70 0.0Wild Oats 60.40 30.0 0.0Cocklebur 80.90 70.60 0.40Morningglory 90.80 20.30 0.0Teaweed 90.90 50.50 0.0Sicklepod 70.50 30.20 0.0Jimsonweed 90.100 70.90 20.30Velvetleaf 90.100 70.60 20.30______________________________________Compound 5POST-EMERGNCERate g/ha 62 16 4______________________________________Corn 80 50 0Wheat 0 0 0Rice 0 0 0Soybean 90 80 60Cotton 60 0 0Sugar beet 70 60 30Rape 100 90 60Crabgrass 0 0 0Johnsongrass 0 0 0Blackgrass 80 0 0Barnyardgrass 0 0 0Nutsedge 0 0 0Giant Foxtail 0 0 0Wild Oats 0 0 0Cocklebur 100 90 70Morningglory 100 90 80Teaweed 50 20 0Sicklepod 0 0 0Jimsonweed 90 80 0Velvetleaf 80 0 0______________________________________PRE-EMERGENCERate g/ha 250 62______________________________________Corn 80 0Wheat 0 0Rice 80 30Soybean 70 20Cotton 20 0Sugar beet 80 20Rape 90 30Crabgrass 0 0Johnsongrass 90 80Blackgrass 90 80Barnyardgrass 70 0Nutsedge 70 20Giant Foxtail 70 0Wild Oats 0 0Cocklebur 90 0Morningglory 90 0Teaweed 60 20Sicklepod 0 0Jimsonweed 90 50Velvetleaf 50 0______________________________________Compound 6POST-EMERGENCERate g/ha 62 16______________________________________Corn 70 40Wheat 50 0Rice 70 30Soybean 90 90Cotton 0 0Sugar beet 80 70Rape 90 70Crabgrass 20 0Johnsongrass 20 0Blackgrass 70 0Barnyardgrass 0 0Nutsedge 0 0Giant Foxtail 0 0Wild Oats 50 0Cocklebur 0 0Morningglory 90 60Teaweed 30 0Sicklepod 50 0Jimsonweed 30Velvetleaf 70 0______________________________________PRE-EMERGENCERate g/ha 250 62______________________________________Corn 40 0Wheat 0 0Rice 90 70Soybean 40 0Cotton 20 0Sugar beet 80 30Rape 60 20Crabgrass 20 0Johnsongrass 70 30Blackgrass 90 60Barnyardgrass 0 0Nutsedge 30 0Giant Foxtail 20 0Wild Oats 0 0Cocklebur 0 0Morningglory 0 0Teaweed 60 0Sicklepod 50 0Jimsonweed 50 30Velvetleaf 50 30______________________________________Compound 8POST-EMERGENCERate g/ha 62 16 4______________________________________Corn 100 90 60Wheat 70 0 0Rice 90 30 0Soybean 100 90 90Cotton 90 20 0Sugar beet 70 20 0Rape 100 90 70Crabgrass 60 0 0Johnsongrass 90 90 70Blackgrass 90 80 20Barnyardgrass 60 20 0Nutsedge 0 0 0Giant Foxtail 40 0 0Wild Oats 40 0 0Cocklebur 80 90 30Morningglory 100 100 90Teaweed 90 80 20Sicklepod 90 60 20Jimsonweed 80 50 0Velvetleaf 100 90 40______________________________________PRE-EMERGENCERate g/ha 250 62 16______________________________________Corn 50 0 0Wheat 40 0 0Rice 100 90 50Soybean 70 0 0Cotton 30 0 0Sugar beet 60 0 0Rape 90 20 0Crabgrass 60 30 0Johnsongrass 90 90 30Blackgrass 90 80 30Barnyardgrass 90 50 0Nutsedge 20 0 0Giant Foxtail 90 50 0Wild Oats 80 20 0Cocklebur 60 0 0Morningglory 0 0 0Teaweed 90 50 20Sicklepod 70 20 0Jimsonweed 90 40 0Velvetleaf 80 30 0______________________________________ .sup.1 Note: there are two sets of data for each rate tested.
Claims
  • 1. A compound of the formula ##STR50## wherein J is selected from ##STR51## n is 0 or 1; L is CH.sub.2 or O;
  • R is H or CH.sub.3 ;
  • R.sub.1 is H, F, Cl, Br, CH.sub.3 or OCH.sub.3 ;
  • R.sub.2 is H or C.sub.1 -C.sub.3 alkyl;
  • R.sub.9 is H, OH, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxyalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.6 alkoxy, phenyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.1 -C.sub.6 alkylcarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, benzyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.3 -C.sub.6 alkylcarbonylalkyl, C.sub.3 -C.sub.6 alkoxycarbonylalkyl or C.sub.1 -C.sub.4 cyanoalkyl;
  • A is ##STR52## X is CH.sub.3, OCH.sub.3, Cl, Br, OCH.sub.2 CF.sub.3 or OCF.sub.2 H; Y is C.sub.1 -C.sub.3 alkyl, CH.sub.2 F, cyclopropyl, C.tbd.CH, OCH.sub.3, OC.sub.2 H.sub.5, OCH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCH.sub.2 CH.sub.2 F, 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, CR(OCH.sub.3).sub.2, ##STR53## CR(OCH.sub.2 CH.sub.3).sub.2 or OCF.sub.2 H; Z is CH; and
  • provided that
  • when X is Cl or Br, then Y is OCH.sub.3, OC.sub.2 H.sub.5, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H.
  • 2. A compound of claim 1 where Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, CH.sub.2 F or CF.sub.3 ; and L is CH.sub.2.
  • 3. A compound of claim 2 where J is J.sub.1, or J.sub.7.
  • 4. A compound of claim 3 where R is H; R.sub.1 is H; and X is CH.sub.3 or OCH.sub.3.
  • 5. A compound of claim 1 wherein R is H; R.sub.9 is H or C.sub.1 -C.sub.3 alkyl; X is CH.sub.3 or OCH.sub.3 ; Y Is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, CH.sub.2 F, or CF.sub.3.
  • 6. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 1 and at least one of (a) a surface active agent, and (b) a solid or liquid diluent.
  • 7. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 2 and at least one of (a) a surface active agent, and (b) a solid or liquid diluent.
  • 8. A composition for the control or undesirable vegetation consisting essentially of a compound of claim 3 and at least one of (a) a surface active agent, and (b) a solid or liquid diluent.
  • 9. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 4 and at least one of (a) a surface active agent, and (b) a solid or liquid diluent.
  • 10. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 5 and at least one of (a) a surface active agent, and (b) a solid or liquid diluent.
  • 11. A method for the control of undesirable vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim 1.
  • 12. A method for the control of undesirable vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim 2.
  • 13. A method for the control of undesirable vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim 3.
  • 14. A method for the control of undesirable vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim 6.
  • 15. A method for the control of undesirable vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim 5.
CROSS-REFERENCE TO RELATED APPLICATION

This application is a division of application Ser. No. 886,151, filed July 16, 1986, now U.S. Pat. No. 4,746,355 which is a division of application Ser. No. 686,796, filed Dec. 26, 1984, now U.S. Pat. No. 4,609,395, which is a continuation-in-part of application Ser. No. 585,170, filed on Mar. 1, 1984, now abandoned.

US Referenced Citations (7)
Number Name Date Kind
4169719 Levitt Oct 1979
4221585 Levitt Sep 1980
4302241 Levitt Nov 1981
4348220 Schwing Sep 1982
4420325 Sauers Dec 1983
4609395 Pasteris et al. Sep 1986
4634465 Ehrenfreund et al. Jan 1987
Foreign Referenced Citations (2)
Number Date Country
71441 Feb 1983 EPX
79683 May 1983 EPX
Divisions (3)
Number Date Country
Parent 886151 Jul 1986
Parent 686796 Dec 1984
Parent 585170 Mar 1984