TREA

Substituted semicarbazone arthropodicieds

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Information

  • Patent Grant
  • 5428027
  • Patent Number
    5,428,027
  • Date Filed
    Thursday, October 28, 1993
    31 years ago
  • Date Issued
    Tuesday, June 27, 1995
    29 years ago
Information
Abstract
Certain substituted semicarbazones, including all geometric and stereoisomers thereof, agricultural compositions containing them and their use as arthropodicides.
Description

BACKGROUND OF THE INVENTION
U.S. Pat. No. 4,547,524 discloses benzoyl hydrazone derivatives as insecticides.
WO 8800197 discloses as part of a broader scope substituted semicarbazones derived from chromanones and thiochromanones as intermediates used in the preparation of insecticides.
EP-3,913 discloses substituted benzophenone hydrazones to be useful as insecticides.
EP-26,040 discloses a broad scope of substituted hydrazones to be useful as insecticides.
EP-254,461 discloses N-substituted hydrazones to be useful as insecticides.
GB-A-1,374,725 discloses structurally related semicarbazide insecticides.
J. Ind. Chem. Soc. 37, pages 443 to 50 (1960) discloses a compound of the formula: ##STR1## but no utility therefor.
SUMMARY OF THE INVENTION
This invention pertains to compounds of Formula I, including all geometric isomers, stereoisomers, and agronomically and nonagronomically suitable salts thereof, compositions containing them, and their use as agronomic and nonagronomic arthropodicides: ##STR2## wherein ##STR3## A is (CH.sub.2).sub.t, O, S(O).sub.q, NR.sub.7, OCH.sub.2 or S(O).sub.q CH.sub.2, wherein, each carbon individually can be substituted with 1 to 2 substituents selected from 1 to 2 halogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.4 -C.sub.7 alkylcycloalkyl, C.sub.2 -C.sub.4 alkoxycarbonyl, or phenyl optionally substituted with 1 to 3 substituent independently selected from W;
R.sub.1 and R.sub.2 are independently R.sub.8, halogen, CN, NO.sub.2, N.sub.3, SCN, OR.sub.8, SR.sub.8, SOR.sub.8, SO.sub.2 R.sub.8, NR.sub.8 R.sub.9, C(O)R.sub.8, CO.sub.2 R.sub.8, C(O)NR.sub.8 R.sub.9, OC(O)R.sub.8, OCO.sub.2 R.sub.8, OC(O)NR.sub.8 R.sub.9, NR.sub.9 C(O)R.sub.8, NR.sub.9 C(O)NR.sub.8 R.sub.9, OSO.sub.2 R.sub.8, NR.sub.9 SO.sub.2 R.sub.8, or when m is 2, R.sub.1 is optionally taken together to form a 5 or 6 membered fused ring as OCH.sub.2 O, OCH.sub.2 CH.sub.2 O OR CH.sub.2 CH.sub.2 O each of which is optionally substituted with 1 to 4 halogen atoms or 1 to 2 methyl groups, or when n is 2, R.sub.2 is optionally taken together to form a 5 or 6 membered fused ring as OCH.sub.2 O, OCH.sub.2 CH.sub.2 O or CH.sub.2 CH.sub.2 O each of which can be substituted 1 to 4 halogens or 1 to 2 methyl groups; R.sub.2 being other than CH.sub.3 when R.sub.1, R.sub.3 and R.sub.4 are H and A is CH.sub.2 ;
R.sub.3 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.4 -C.sub.6 alkylcycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, OR.sub.8, S(O).sub.q R.sub.8, NR.sub.8 R.sub.9, CN, CO.sub.2 R.sub.8, C(O)R.sub.8, C(O)NR.sub.8 R.sub.9, C(S)NR.sub.8 R.sub.9, C(S)R.sub.8, C(S)SR.sub.8, phenyl optionally substituted with (R.sub.10).sub.p or benzyl optionally substituted with 1 to 3 substituents independently selected from W or R.sub.3 is C.sub.3 -C.sub.6 cycloalkyl optionally substituted with 1 to 2 halogens or 1 to 2 CH.sub.3 ;
R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 cyanoalkyl, phenyl optionally substituted with (R.sub.10).sub.p or benzyl optionally substituted with 1 to 3 substituents independently selected from W;
R.sub.5 and R.sub.6 are independently H, C.sub.1 -C.sub.22 alkyl, C.sub.2 -C.sub.22 alkoxyalkyl, C.sub.2 -C.sub.22 alkylcarbonyl, C.sub.2 -C.sub.22 alkoxycarbonyl, C.sub.2 -C.sub.22 haloalkyl carbonyl, C.sub.2 -C.sub.22 haloalkoxycarbonyl, SR.sub.11, CHO, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfonyl optionally substituted with 1 to 3 substituents independently selected from W; C.sub.7 -C.sub.15 phenoxycarbonyl optionally substituted with 1 to 3 substituents selected from W; C.sub.7 -C.sub.15 phenylcarbonyl optionally substituted with 1 to 3 substituents independently selected from W; C(O)CO.sub.2 C.sub.1 to C.sub.4 alkyl, C.sub.8 -C.sub.12 benzyloxycarbonyl optionally substituted with 1 to 3 substituents independently selected from W; or R.sub.5 and R.sub.6 are independently phenyl optionally substituted with 1 to 3 substituents independently selected from W, or benzyl optionally substituted with 1 to 3 substituents independently selected from w;
R.sub.7 is H, C.sub.1 -C.sub.4 alkyl or phenyl optionally substituted with W; SR.sub.8, SOR.sub.8, SO.sub.2 R.sub.8, C(O)R.sub.8, CO.sub.2 R.sub.8, C(O)NR.sub.8 R.sub.9, C(S)NR.sub.8 R.sub.9, C(S)R.sub.8, C(S)OR.sub.8, P(O) (OR.sub.8).sub.2, P(S) (OR.sub.8).sub.2, P(O) (R.sub.8)OR.sub.8 or P(O) (R.sub.8)SR.sub.8 ; provided that when R.sub.7 is other than COR.sub.8, C(O)NR.sub.8 R.sub.9 or C(S)NR.sub.8 R.sub.9 then R.sub.8 is other than H;
R.sub.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.4 -C.sub.7 halocycloalkylalkyl C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W or benzyl optionally substituted with 1 to 3 substituents independently selected from W;
R.sub.9 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, or R.sub.8 and R.sub.9 is optionally taken together as (CH.sub.2).sub.4, (CH.sub.2).sub.5 or (CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2);
R.sub.10 is R.sub.8, halogen, CN, NO.sub.2, N.sub.3, SCN, OR.sub.8, SR.sub.8, SOR.sub.8, SO.sub.2 R.sub.8, NR.sub.8 R.sub.9, COR.sub.8, CO.sub.2 R.sub.8, CONR.sub.8 R.sub.9, SO.sub.2 NR.sub.8 R.sub.9, OC(O)R.sub.8, OCO.sub.2 R.sub.8, OC(O)NR.sub.8 R.sub.9, NR.sub.9 C(O)R.sub.8, NR.sub.9 C(O)NR.sub.8 R.sub.9, OSO.sub.2 R.sub.8, NR.sub.9 SO.sub.2 R.sub.8 or when p is 2, R.sub.10 is optionally taken together to form a 5 or 6 membered fused ring as OCH.sub.2 O, OCH.sub.2 CH.sub.2 O, or CH.sub.2 CH.sub.2 O each of which is optionally substituted with independently, 1 to 4 halogen atoms or 1 to 2 methyl groups;
R.sub.11 is C.sub.1 -C.sub.22 alkyl, C.sub.1 -C.sub.22 haloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W, or R.sub.11 is NR.sub.12 C(O)R.sub.13, NR.sub.12 S(O).sub.a R.sub.13, ##STR4## R.sub.12 and R.sub.16 are independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.4 -C.sub.8 dialkylaminocarbonylalkyl, phenyl optionally substituted by 1 to 2 substituents selected from W, benzyl optionally substituted by 1 to 2 substituents selected from W and phenethyl optionally substituted by 1 to 2 substituents selected from w, or R.sub.12 -R.sub.16 is optionally taken together as (CH.sub.2).sub.4, (CH.sub.2).sub.5 or (CH.sub.2).sub.2 O(CH.sub.2).sub.2, each ring optionally substituted with 1 to 2 CH.sub.3 ;
R.sub.13 is F, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.8 dialkylamino, piperidenyl, pyrrolidenyl, morpholinyl, phenyl optionally substituted with 1 to 3 substituents selected from W, or R.sub.13 is C.sub.1 -C.sub.20 alkoxy C.sub.1 -C.sub.6 haloalkoxy or C.sub.1 -C.sub.4 alkoxy substituted with cyano, nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.4 -C.sub.8 alkoxyalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.2 -C.sub.3 alkoxycarbonyl, C.sub.3 -C.sub.5 dialkylaminocarbonyl or phenyl optionally substituted with 1 to 3 substituents independently selected from W, or R.sub.13 is phenoxy optionally substituted with 1 to 3 substituents selected from W;
R.sub.14 and R.sub.15 are independently selected from C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 haloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W or R.sub.14 and R.sub.15 is optionally taken together as (CH.sub.2).sub.2, (CH.sub.2).sub.3 or CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 ;
W is halogen, CN, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 alkylsulfonyl or C.sub.1 -C.sub.2 haloalkylsulfonyl;
m is 1 to 5;
n is 1 to 4;
t is 0 to 3;
q is 0 to 2;
p is 1 to 3;
a is 0 to 2;
V is O or S;
X is O or S; X being O when A is CH.sub.2 and R.sub.2, R.sub.3 and R.sub.4 are H;
Y is O or S; and
Z is O or S.
Preferred Compounds (A) are those compounds of Formula I wherein;
when R.sub.3 or R.sub.4 is H and A is oxygen then the remaining R.sub.3 or R.sub.4 is other than phenyl or phenyl optionally substituted with W and when t is 0 then R.sub.3 or R.sub.4 are other than Ph or phenyl optionally substituted with W.
Preferred Compounds (B) are Compounds of Formula I wherein;
R.sub.1, R.sub.2 and R.sub.10 are R.sub.8, halogen, CN, NO.sub.2, OR.sub.8, SR.sub.8, SOR.sub.8, SO.sub.2 R.sub.8, NR.sub.8 R.sub.9, CO.sub.2 R.sub.8, SO.sub.2 NR.sub.8 R.sub.9, or when m, n or q is 2, then R.sub.1, R.sub.2 or R.sub.10 respectively is optionally taken together to form a 5 or 6 membered fused ring as OCH.sub.2 O, OCH.sub.2 CH.sub.2 O or CH.sub.2 CH.sub.2 O each of which is optionally substituted with 1 to 4 halogens or 1 to 2 methyl groups;
R.sub.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 cycloalkylalkyl, C.sub.3 -C.sub.6 halocycloalkylalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl optionally substituted with 1 to 2 substituents independently selected from w or benzyl optionally substituted with 1 to 2 substituents independently selected from W;
R.sub.5 and R.sub.6 are independently H, C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl, CHO, SR.sub.11, phenyl optionally substituted with 1 to 2 substituents independently selected from W, or benzyl optionally substituted with 1 to 2 substituents independently selected from W;
R.sub.11 is C.sub.1 -C.sub.3 alkyl, phenyl optionally substituted with 1 to 2 substituents independently selected from W, NR.sub.12 C(O)R.sub.13, NR.sub.12 S(O).sub.a R.sub.13, C(O)R.sub.13, NR.sub.12 R.sub.16 ; ##STR5## R.sub.12 and R.sub.16 are independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, phenyl, benzyl and phenethyl or each phenyl, benzyl and phenethyl optionally substituted with 1 to 2 substituents independently selected from W, or R.sub.12 and R.sub.16 can be taken together as (CH.sub.2).sub.4, (CH.sub.2).sub.5 or (CH.sub.2).sub.2 O(CH.sub.2).sub.2 ;
R.sub.14 and R.sub.15 are independently selected from C.sub.1 to C.sub.3 alkyl or phenyl;
m is 1 to 2;
n is 1 to 2;
p is 1 to 2;
q is 0;
V is S; and
a is 2.
Preferred Compounds (C) are Compounds B wherein:
R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, CN, phenyl optionally substituted with (R.sub.10).sub.p or benzyl optionally substituted with 1 to 2 substituents independently selected from W;
R.sub.4 is H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl;
R.sub.5 is H, Me, CO.sub.2 Me, CO.sub.2 Et, SR.sub.11 or phenyl optionally substituted with 1 to 2 substituents independently selected from W;
R.sub.6 is H, Me, C(O)Me, CO.sub.2 Me or SR.sub.11 ;
R.sub.11 is C.sub.1 -C.sub.3 alkyl, NR.sub.12 C(O)R.sub.13, NR.sub.12 S(O).sub.a R.sub.13, C(O)R.sub.13, or phenyl optionally substituted with Cl, NO.sub.2 or CH.sub.3 ;
R.sub.12 is C.sub.1 -C.sub.4 alkyl or phenyl optionally substituted with Cl or CH.sub.3 ;
R.sub.13 is C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 haloalkyl, dimethylamino, phenyl optionally substituted with Cl or CH.sub.3, or R.sub.13 is C.sub.1 -C.sub.4 alkoxy substituted with C.sub.2 -C.sub.4 alkoxy or 1 to 6 halogens;
A is CH.sub.2, CH.sub.2 CH.sub.2, O, S, OCH.sub.2, NR.sub.7 or SCH.sub.2, wherein, each carbon is optionally substituted with C.sub.1 -C.sub.3 alkyl or phenyl, wherein, the phenyl is optionally substituted with w; and;
R.sub.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl or C.sub.1 -C.sub.4 alkylsulfonyl.
Preferred Compound (D) are Compounds C wherein:
R.sub.1 and R.sub.2 are independently selected from F, Cl, Br, CN, NO.sub.2, OMe, CF.sub.3, OCF.sub.2 H, OCF.sub.2 CF.sub.2 H, SMe, SO.sub.2 Me, SCF.sub.2 H or when m or n is 2 R.sub.1 or R.sub.2 respectively is optionally taken together as CH.sub.2 C(CH.sub.3).sub.2 O or CF.sub.2 CF.sub.2 O;
R.sub.3 is C.sub.1 to C.sub.4 alkyl, allyl, propargyl, or phenyl optionally substituted with F, Cl, Br, CF.sub.3, OCF2H, OCF.sub.3, SCF.sub.2 H, CN, NO.sub.2, CH.sub.3, OMe or CO.sub.2 Me;
R.sub.4 is H or CH.sub.3 ;
R.sub.5 is H, CH.sub.3 CO.sub.2 CH.sub.3, CO.sub.2 Et, or phenyl optionally substituted with F or Cl;
R.sub.6 is H, CH.sub.3, C(O)CH.sub.3 or CO.sub.2 CH.sub.3 ; and
A is O, S or CH.sub.2, optionally substituted with C.sub.1 -C.sub.3 alkyl or phenyl which may also be optionally substituted with W.
Preferred Compounds (E) are Compounds D wherein A is CH.sub.2 ; and R.sub.3 is optionally substituted phenyl or C.sub.1 to C.sub.4 alkyl. Preferred Compounds (F) are compounds of Formula I wherein Q is Q-1. Preferred Compounds (G) are compounds of Formula I wherein Q is Q-2. Preferred Compounds (H) are compounds of Formula I wherein Q is Q.sub.3. Preferred Compounds (I) are compounds of Formula I wherein Q is Q.sub.4. Preferred Compounds (J) are compounds of Formula I wherein Q is Q.sub.5. Preferred Compounds (K) are compounds of Formula I wherein Q is Q.sub.6. Preferred Compounds (L) are compounds of Formula I wherein Q is Q.sub.7. Preferred Compounds (M) are compounds of Formula I wherein Q is Q.sub.8. Preferred Compounds (N) are Compounds (E) wherein Q is Q-1.
Specifically preferred are the compounds:
O) 2-[5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl-idene]-N-[4- (trifluoromethoxy)phenyl]hydrazine carboxamide;
P) 2-[6-chloro-2,3-dihydro-2-methyl-2-(2-propenyl)-3-benzo-furanylidene]-N-[4-(trifluoromethoxy)phenyl]hydrazine carboxamide;
Q) 2-(5-fluoro-2 ,3-dihydro-2-methyl-1H-inden-1-ylidene)-N-[4-(trifluoromethyl) phenyl ]hydrazine carboxamide;
R) 2-[5-chloro-2 ,3-dihydro-2-(1-methylethyl)-1H-inden-1-ylidene]-N-[4-(trifluoro methyl)phenyl]hydrazine carboxamide;
S) 2-(5-chloro-2, 3-dihydro-2-methyl-1H-inden-1-ylidene)-N-[4-(trifluoromethyl) phenyl]hydrazine carboxamide; and
T) 2-[5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl -idene]-N-[4-(trifluoromethyl)phenyl]hydrazine carboxamide.





DETAILS OF THE INVENTION
The compounds of Formula I, where Q is Q-1, can be prepared by the reaction of hydrazones of Formula II with an aryl isocyanate of Formula III. Compounds of Formula I, where Q is Q-2 through Q-8, can be prepared by procedures which are analogous to those for compounds where Q is Q-1; therefore, for brevity only the Q-1 compounds are described. Typical reactions involve combination of equimolar amounts of II and III in a suitable solvent at temperatures generally in the range of -10.degree. to 100.degree. C. Although the reaction can be run neat, a solvent is generally preferred. Suitable solvents typically have sufficient polarity to effect solution of the Formula II hydrazone and include, but are not limited to, ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; aromatic hydrocarbons such as benzene, toluene and xylene; esters such as ethyl acetate and polar aprotic solvents such as dimethylformamide and dimethylacetamide. ##STR6##
Compounds of Formula I include both geometrical and optical isomers as well as syn and anti isomers around the nitrogen-nitrogen bond. These isomers may vary in their biological activity. In some instances, it may be desirable to obtain compounds which are geometrically and/or optically pure or which are enriched in one or more of the possible isomers. All such isomers are included within the scope of this invention.
For the sake of simplifying the description of this invention, the generic formula (Formula I) encompasses certain compounds that may have long term stability problems and/or are difficult to prepare. For example, when R.sub.1 is an OCO.sub.2 R.sub.8 group and R.sub.8 is hydrogen the R.sub.1 substituent is OCO.sub.2 H which will decompose to the corresponding phenol and carbon dioxide. Similarly, haloalkylamines when R.sub.1 is NR.sub.8 R.sub.9 and R.sub.8 is C.sub.1 to C.sub.6 haloalkyl are unstable when the halo substituent is directly adjacent to nitrogen. These generally decompose to the corresponding hydrogen halides and imine. These compounds, however, are relatively few; their identity would be obvious to one skilled in the art, and their excision from the scope would unduly complicate and lengthen the description of the invention.
The hydrazones of Formula II can be obtained by processes known in the art involving condensation of a ketone of Formula IV with either hydrazine or a substituted derivative thereof (Formula V). This reaction is typically conducted with equimolar amounts of IV and V although greater than stoichiometric amounts of hydrazine (V) can be used. Suitable solvents include the alcohols such as methanol, ethanol, propanol, butanol and the like at temperatures in the range of 0.degree. to 150.degree. C., with the reflux temperature of the solvent generally being a convenient reaction temperature. Acid catalysis can also be useful, particularly for some of the more sterically hindered Formula IV compounds. Typical acid catalysts include sulfuric, hydrochloric and p-toluene sulfonic acid. ##STR7##
An alternate process useful for the preparation of compounds of Formula I involves condensation of a phenyl substituted semicarbazide of Formula VI with a ketone of Formula III. Preferred conditions for this reaction include an acid catalyst such as hydrochloric, sulfuric or p-toluene sulfonic acid. Reaction temperatures can range from 0.degree. to 150.degree. C. with the reflux temperature of the solvent used generally preferred. Suitable solvents include, but are not limited to, ethers such as tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene and toluene; and especially preferred are alcohols such as methanol, ethanol and isopropanol. ##STR8##
Compounds of Formula I where R.sub.5 and R.sub.6 are other than hydrogen can generally be prepared from the corresponding compounds where R.sub.5 and R.sub.6 are hydrogen by reaction with electrophilic reagents such as alkyl halides, acyl halides, alkyl chloroformates and sulfenyl halides. The use of a base is generally preferred in these reactions but is dependent upon the specific nature of the reactants. For example, when the electrophilic reagent is selected from an alkyl halide, acyl halide or alkyl chloroformate, then metal hydrides such as sodium hydride or potassium hydride in solvents such as tetrahydrofuran or dimethylformamide are preferred. When sulfenyl halides are used then amine bases such as triethylamine in solvents such as diethyl ether or tetrahydrofuran are generally preferred. Of course, many of the compounds where R.sub.5 is other than H can also be prepared by use of the appropriate hydrazine V in Scheme 2. For example, methyl hydrazine and methyl carbazate will produce compounds where R.sub.5 is methyl and carbomethoxy, respectively.
The starting ketones of Formula II are known or can be obtained by processes analogous to known ones. Those skilled in the art will recognize the Formula II compounds to include indanones, tetralones, chromanones, thiochromanones, benzofuran-3-ones, thiobenzofuran-3-ones, isochromanones, isothiochromanones and others.
The following Examples illustrate the invention.
EXAMPLE 1
Step A: 3-chloro-.alpha.-(4-chlorophenyl)benzenepropanoic acid
To a solution of 6.8 g (0.17 mol) of 60% sodium hydride in 150 ml of dimethylformamide under nitrogen was added 30.0 g (0.162 mol) of methyl 4-chlorophenylacetate dropwise such that hydrogen evolution was moderate and the temperature of the reaction was maintained at less than 50.degree. C. Once hydrogen evolution had ceased, a solution of 3-chlorobenzylbromide in 30 ml of dimethylformamide was added very cautiously such that the reaction temperature was maintained at less than 60.degree. C. The reaction was maintained at 50.degree. to 60.degree. C. with stirring overnight after which time it was partitioned between 5% aqueous NaHCO.sub.3 and diethyl ether, the aqueous extracts were washed twice with ether and the combined organic extracts were then washed with water. The ether extracts were dried over MgSO.sub.4, filtered and concentrated to afford 48.0 g of a brown oil.
The crude product was combined with 300 ml of methanol, 40 ml of water and 20 ml of 50% aqueous sodium hydroxide and refluxed overnight. After this time the reaction was concentrated and the crude residue partitioned between water and ether. The aqueous extracts were acidified with conc. hydrochloric acid and extracted several times with ether. The ether extracts were dried over MgSO.sub.4, filtered and concentrated to 48.8 g of a yellow, oily solid. .sup.1 H NMR (CDCl.sub.3) .delta. 3.0 (dd, 1H), 3.3 (m, 1H), 3.84 (t, 1H), 6.77 (d, 1H), 6.9-7.4 (m) .
Step B: 5-chloro-2-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-one
The crude product from Step A was combined with 50 ml of thionyl chloride and then heated at reflux for 2 hours. Thionyl chloride was removed by concentration at reduced pressure and then the mixture was concentrated several times from carbon tetrachloride. The residue was combined with 200 ml of dichloroethane, cooled under nitrogen to 0.degree. C., and 24.5 g of aluminum trichloride was then added. After stirring overnight the reaction was poured onto a mixture of ice in 1N hydrochloric acid, extracted three times with ether and chromatographed on silica gel (10% ethyl acetate/hexane) to afford 18.6 g of a yellow oily solid. .sup.1 H NMR (CDCl.sub.3) .delta. 3.20 (dd, 1H), 3.68 (dd, 1H), 3.90 (dd, 1H), 6.9-7.6 (m), 7.75 (d, 1H) .
Step C: 2-[5-chloro-2-(4-chlorophenyl)-2,3-dihydro 1H-inden-1-ylidene]-N-[4-trifluoromethyl)-phenyl]hydrazinecarboxamide
A mixture of 1.5 g of the indanone from Step B and 0.75 ml of hydrazine hydrate in 10 ml of ethanol was refluxed under N.sub.2 overnight. The mixture was then partitioned between 5% NaHCO.sub.3 and ether, the aqueous extracts were washed with chloroform and the combined chloroform/ether extracts were washed with water. The organic extracts were dried over magnesium sulfate and concentrated to 1.54 g of a yellow oil. To 0.45 g of this oil was added 10 ml of THF and 0.29 g of 4-trifluoromethylphenyl isocyanate. The mixture was then stirred under nitrogen overnight. Concentration at reduced pressure and then trituration with ether provided 0.27 g of the title compound as a yellow solid, m.p. 214.degree. to 216.degree. C. .sup.1 H NMR (CDCl.sub.3) .delta. 2.95 (dd, 1H), 3.74 (dd, 1H), 4.30 (dd, 1H), 7.1-7.8 (m), 8.33 (s, 1H); IR (nujol) 1680, 3190, 3360 cm.sup.-1.
EXAMPLE 2
Step A: ethyl 2[5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-ylidene]hydrazine carboxylate
To a mixture of 1.5 g of 5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one (prepared by a procedure analogous to Example 1, Step B) and 0.63 g of ethyl carbazate in 20 ml of methanol was added 1 drop of conc. H.sub.2 SO.sub.4 and the reaction was refluxed under nitrogen overnight. The reaction was then partitioned between ethyl acetate and 5% aqueous NaHCO.sub.3, the aqueous extracts were washed with ethyl acetate and the combined organic extracts were dried over MgSO.sub.4. Concentration of the organic extract afforded 1.9 g of a yellow oil, which was triturated with ether to afford 1.27 g of a white solid, m.p. 139.degree.-141.degree. C. .sup.1 H NMR (CDCl.sub.3) .delta. 1.26 (t, 3H), 2.91 (dd, 1H), 3.70 (dd, 1H), 4.2 (m, 3H), 6.9-7.3 (m, 6H), 7.52 (bs, 1H ), 7.93 (dd, 1H ).
Step B: ethyl 2-[5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-ylidene]-1-[[[4-trifluoromethyl)phenyl]amino]carbonyl]-hydrazine carboxylate
To a solution of 1.02 g of the ethyl carboxylate from Step A and 0.62 g of 4-trifluoromethylphenylisocyenate in 10 ml of THF was added 0.26 ml of triethylamine and the mixture was stirred under nitrogen overnight. The reaction was then partitioned between ethyl acetate and 5% aqueous NaHCO.sub.3 and the aqueous extracts were washed twice with ethyl acetate. The organic extracts were dried over MgSO.sub.4 and concentrated to 1.67 g of a yellow oil. Chromatography on silica gel afforded 0.37 g of a yellow solid m.p. 144-146. .sup.1 H NMR (CDCl.sub.3) .delta. 1.16 (t, 3H), 3.00 (dd, 1H), 3.65 (dd, 1H), 3.8-3.9 (m, 1H), 4.0-4.1 (m, 1H), 4.32 (dd, 1H), 6.85-7.2 (m, 6H), 7.60 (s, 4H), 8.05 (dd, 1H), 10.66 (s, 1H).
EXAMPLE 3
Step A: N-[4-trifluoromethyl)phenyl]hydrazine carboxamide
To a 0.degree. C. solution of 10 ml of hydrazine hydrate and 75 ml of THF was added dropwise a solution of 6 g of 4-trifluoromethyl phenyl isocyanate in 20 ml of THF. After 1 hr TLC indicated the reaction was complete. The reaction was partitioned between ether and water, the ether extracts were washed twice with water, dried over MgSO.sub.4, and concentrated to 6.34 g of a white solid, m.p. 168.degree.-172.degree. C. .sup.1 H NMR (CDCl.sub.3) .delta. 3.9 (bm, 2H), 6.1 (bs, 1H), 7.56 (d, 2H), 7.61 (d, 2H), 8.4 (bs, 1H).
Step B: methyl 5-chloro-2,3-dihydro-2-methyl-1-oxo-1H-indene-2-carboxylate
To a mixture of 8.0 g of 5-chloroindanone and 4.2 ml of dimethylcarbonate in 60 ml of THF was added 4.0 g of 60% NaH and the mixture was heated to reflux under N.sub.2 overnight. After this time the reaction was cooled to room temperature and 4.0 ml of methyl iodide was added and the mixture was reheated to reflux overnight. The reaction was then cooled and partitioned between ether and 5% aqueous NaHCO.sub.3 and the aqueous extracts were washed twice with ether. The combined aqueous extracts were dried over MgSO.sub.4 and concentrated to 11.24 g of a brown oil. Chromatogrpahy on silica gel (10% ethyl acetate/hexane) afforded 4.25 g of the title compound as a brown oil. .sup.1 H NMR (CDCl.sub.3) .delta. 1.52 (s, 3H), 2.96 (d, 1H), 3.68 (s, 3H), 3.69 (d, 1H), 7.40 (d, 1H), 7.47 (s, 1H), 7.71 (d, 1H).
Step C: methyl 5-chloro-2,3-dihydro-2-methyl-1-[[[[4 -(trifluoromethyl)phenyl]amino]carbonyl]hydrazine]-1H-indene-2-carboxylate
To a mixture of 0.92 g of the compound from Step A and 1.0 g of the compound from Step B in 10 ml of methanol was added 1 drop of conc. H.sub.2 SO.sub.4 and the mixture was heated to reflux under N.sub.2 overnight. The reaction was then cooled to 0.degree. C. and the precipitate filtered, rinsed with cold methanol and dried to 0.39 g of a brown solid, m.p. 192.degree.-194.degree. C. .sup.1 H NMR (CDCl.sub.3) .delta. 1.70 (s, 3H), 3.00 (d, 1H), 3.82 (s, 3H), 3.87 (d, 1H), 7.3 (m, 2H), 7.6-7.8 (m, 5H), 8.38 (s, 1H), 8.98 (s, 1H).
EXAMPLE 4
Step A: 3-(4-fluorophenyl)-1-phenyl-2-propen-1-one
To a mechanically stirred solution of 5.0 g NaOH in 35 ml H.sub.2 O and 25 ml EtOH at 15.degree. C. was added 12.0 g (0.100 mole) of acetophenone and 12.4 g (0.100 mole) of 4-fluorobenzaldehyde. After a brief exotherm to 25.degree. C., the temperature returned to 15.degree. C., and the cooling bath was removed. The reaction mixture was stirred at room temperature for 1.5 hour, and the thick slurry was transferred to a beaker to cool overnight at 10.degree. C. This mixture was filtered, and the solids were washed with distilled H.sub.2 O until the washings were neutral to litmus. Upon drying in vacuo, 20.8 g of a pale yellow solid was obtained, m.p. 86.degree.-87.degree. C. IR (Nujol): 1660, 1605, 1590, 1580 cm.sup.-1. .sup.1 H NMR (200 MHz, CDCl.sub.3): .delta. 7.12 (d, J=16 Hz, 1H), 7.42-7.68 (m, 7H), 7.78 (d, J=16 Hz, 1H), 8.02 (m, 2H).
Step B: 3-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-one
The title compound of Step A, Example 4, 11.3 g (0.50 mole), was added to 250 ml of mechanically-stirred polyphosphoric acid at 135.degree. C., under a nitrogen atmosphere. This mixture was heated at 135.degree. C. for 2 hours and then allowed to cool to 90.degree. C. Ice water was added at such a rate as to maintain a temperature below 125.degree. C. Once the material had become fluid, it was poured over ice and extracted with ether. The ether extracts were washed twice with saturated aqueous NaHCO.sub.3 and once with brine. The ethereal solution was dried over MgSO.sub.4 and concentrated at reduced pressure. The resultant residue was recrystallized from hexane/chlorobutane to afford 5.90 g of the title compound as a brown powder, m.p. 117.degree.-120.degree. C. IR (Nujol): 1705 (s), 1600 (br, m) .sup.1 H NMR (200 MHz, CDCl.sub.3 ): .delta. 2.64 ( dd, 1H), 3.22 (dd, 1H), 4.57 (dd, 1H), 6.96-7.15 (m, 4H), 7.25 (m, 1H), 7.44 (m, 1H), 7.58 (m, 1H), 7.81 (m, 1H).
Step C: 2-[3-(4-fluorophenyl)-2,3-dihydro-1H-inden-1ylidene]-N-[4-(trifluoromethyl)phenyl]hydrazine carboxamide
The title compound of Step B, Example 4, 2.26 g (0.010 mole), was combined with 0.60 ml of hydrazine monohydrate (0.012 mole) in 30 ml of methanol and heated at reflux for 2 to 2.5 hours. The reaction mixture was concentrated at reduced pressure, and the resultant residue was dissolved in ethyl acetate and washed with saturated aqueous NaHCO.sub.3, H.sub.2 O, and brine. The organic phase was dried over MgSO.sub.4 and concentrated in vacuo to afford 2.37 g of crude material. This material was dissolved in 30 ml of dry THF, and a 10 ml aliquot of this solution was added to a solution of 0.62 g (0.0033 mole) of 4-(trifluoromethyl)phenyl isocyanate in 20 ml of dry THF. After this mixture was stirred overnight under a nitrogen atmosphere, it was concentrated in vacuo. The resultant residue was triturated with hexanes and filtered to obtain 1.23 g of an off-white product, m.p. 253.degree.-255.degree. C. .sup.1 H NMR (200 MHz, d.sub.6 -DMSO): .delta. 2.74 (dd, 1H), 3.38 (dd, 1H), 4.65 (dd, 1H), 7.0-7.16 (m, 5H), 7.33-7.37 (m, 2H), 7.63-7.67 (m, 2H), 7.91-7.95 (m, 2H), 8.08 (m, 1H), 9.30 (s, NH), 10.00 (s, NH).
EXAMPLE 5
Step A: ethyl 4-fluoro-methylenebenzeneacetate
Sodium ethoxide solution was prepared by portionwise addition of sodium pieces (1.5 g, 0.065 mol) to ethanol (50 ml). To this solution was added first, 8.9 ml (0.065 mol) of diethyloxalate in one portion and second, 10 g (0.059 mol) of methyl 4-fluorobenzeneacetate dropwise at such a rate as to keep the reaction mixture at 25.degree. C. After stirring at room temperature for 2 hrs, the ethanol was concentrated and the residue taken up in toluene. The toluene solution was concentrated and the solid residue was taken up in ether and 10% aqueous acetic acid. After stirring at room temperature for 1 hr the mixture was separated and the aqueous phase extracted twice with ether. The combined ether phases were washed once with saturated aqueous NaHCO.sub.3 solution, dried (MgSO.sub.4), and concentrated. The NMR of the crude product was complicated by a mixture of methyl and ethyl esters.
The crude diester was combined with 25 ml of water and 8 ml of 37% formalin solution. To this somewhat heterogeneous mixture was added a solution of 6.5 g of K.sub.2 CO.sub.3 in 36 ml of water, dropwise as such a rate as to maintain a temperature of about 25.degree. C. The reaction was stirred vigorously for three hours to mix the fine emulsion. Ether was added and the aqueous phase was separated and extracted three times with ether. The combined ether phases were dried (MgSO.sub.4) and concentrated to a colorless oil (11 g, 96% yield). .sup.1 H NMR (CDCl.sub.3) .delta.: 7.41 (2H, m), 7.03 (2H, m), 6.34 (1H, s), 5.85 (1H, s), 4.28 (2H, q, J=7 Hz), 1.32 (3H, t, J=7 Hz).
Step B: ethyl 4-fluoro-.alpha.-[[(2-fluorophenyl)thio]methyl]benzeneacetate
The crude product from Step A (3.9 g, 20 mole) was taken up in 20 ml of ethanol. To this solution, being stirred at room temperature, was added 2-fluorothiophenol (2.5 g, 20 mmole) and 50 mg of solid sodium ethoxide. After stirring for eight hours the ethanol was concentrated and the residue taken up in ether. The ether mixture was washed twice with 15% NaOH solution, dried (MgSO.sub.4) and concentrated to a colorless oil (5.3 g, 82% yield). .sup.1 H NMR (CDCl.sub.3) .delta.: 7.28 (4H, m), 7.06 (4H, m), 4.13 (2H, m), 3.72 (1H, m), 3.55 (1H, m), 3.20 (1H, dd, J=6, 12 Hz), 1.21 (3H, t, J=6 Hz).
Step C: 4-fluoro-.alpha.-[[(2-fluorophenyl)thio]methyl]benzeneacetic acid
The crude ester from Step B (5.3 g, 16 mmole) was combined with 20 ml of 88% formic acid and 2.1 ml (33 mmole) of methane sulfonic acid. The emulsion was refluxed for five hours during which time it gradually became homogeneous. After cooling, water and methylene chloride were added and the aqueous phase was separated and extracted twice with methylene chloride. The organic phases were combined, dried (MgSO.sub.4) and concentrated. The crude residue was taken up in 4% ethyl acetate/hexane and filtered through a plug of silica gel to remove nonpolar impurities. The product acid was then rinsed from the silica gel with ethyl acetate and the solvent concentrated. The acid was a colorless solid (4.5 g, 95% yield). .sup.1 H NMR (CDCl.sub.3) .delta.: 10.05 (1H, br s), 7.20 (5H, m), 7.03 (3H, m), 3.81 (1H, dd, J=6, 8 Hz), 3.57 (1H, m), 3.23 (1H, dd, J= 6, 12 Hz).
Step D: 8-fluoro-3-(4-fluorophenyl)-2,3-dihydro-4H-1-benzothiopyran-4 -one
The acid from Step C (4.5 g, 15 mmole) was dissolved in 30 ml of thionyl chloride and refluxed for four hours. After cooling the thionyl chloride was concentrated and the residue taken up in carbon tetrachloride. The carbon tetrachloride was concentrated and the residue was taken up in 30 ml of dichloroethane. To the dichloroethane solution being cooled in an ice bath, was added aluminum trichloride (total of 2.1 g, 16 mmole) in three portions every 15 min. After stirring the black solution for an additional 30 min at 0.degree. C., a 5% aqueous HCl solution was added. The aqueous phase was separated and extracted twice with methylene chloride. The organic phases were combined, dried (MgSO.sub.4), and concentrated to give the crude product as a yellow oil (3.4 g, 82% yield). .sup.1 H NMR (CDCl.sub.3) .delta.: 7.97 (1H, dd, J=3, 9 Hz), 7.19 (6H, m), 4.12 (1H, dd, J=4, 12 Hz), 3.58 (1H, m), 3.32 (1H, ddm J=4, 12 Hz).
Step E: 2-[8-fluoro-3-(4-fluorophenyl)-3,4-dihydro-2 H- 1-benzothiopyran-4-ylidene]-N-[4-(trifluoromethyl)phenyl]-hydrazinecarboxamide
The thiochromanone from Step D (1.1 g, 4.0 mmole) was treated according to the procedure in Example 1 Step C to give the desired product as a white powder (0.32 g, 17% yield) m.p.=217.degree.-219.degree. C. .sup.1 H NMR (CDCl.sub.3) .delta.: 8.33 (1H, s), 7.98 (1H, d, J=9 Hz), 7.69 (1H, s) 7.60 (4H, AB, J.sub.AB =8 Hz), 7.15 (6H, m), 4.42 (1H, t, J=4 Hz), 3.44 (1H, dd, J=4, 12 Hz), 2.99 (1H, dd, J=4, 12 Hz).
EXAMPLE 6
Step A: methyl 6-fluoro-1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate
Hexane washed sodium hydride (3.5 g of 60%, 88 mmole) was covered with 75 ml of tetrahydrofuran and 5.4 ml (64 mmole) of dimethylcarbonate was added in one portion. The solution was heated to reflux and 6-fluoro-3,4-dihydro-1(2H)-naphthlenone (7.2 g, 44 mmole) in 25 ml of tetrahydrofuran was added dropwise while maintaining reflux. After the addition was complete, the reaction was refluxed for 1.5 hours. The reaction was then cooled in an ice bath and 10% aqueous HCl solution was carefully added. The solution was diluted with ether and the aqueous phase was separated and extracted twice with ether. The combined organic phases were dried (MgSO.sub.4) and concentrated. The crude product was a pale yellow solid (9.6 g, 98% yield). .sup.1 H NMR (CDCl.sub.3) .delta.: 7.99 (1H, dd, J=6,8 Hz), 6.95 (2H, m) 3.83 (3H, s), 3.82 (1H, m), 2.81 (2H, m), 2.58 (2H, m). NMR complicated by signals from enol tautomer.
Step B: methyl 6-fluoro-1,2,3,4-tetrahydro-1-oxo-2-phenyl-2-naphthalenecarboxylate
The tetralone from Step A (2.4 g, 10.8 mmole) and triphenylbismuth dichloride (5.8 g, 11.3 mmmole) were dissolved in 50 ml of benzene. 1,8-Diazabicyclo-[5.4.0]-undec-7-ene (1.8 ml, 11 .8 mmole) was added and the pale yellow solution was heated at reflux for 12 hours. The benzene solution was decanted from the gray sludge. The sludge was in turn triturated twice with ether and twice with acetone. The combined benzene, ether, and acetone phases were washed once with water, dried (MgSO.sub.4), and concentrated. The resulting residue was flash chromatographed on silica gel eluting with 10% acetone/hexane. Purified product was obtained in 90% yield (2.9 g) as a viscous oil which solidified on standing. .sup.1 H NMR (CDCl.sub.3) .delta.: 8.17 (1H, dd, J=8,10 Hz), 7.31 (5H, m) 7.02 (1H, dt, J=3,8 Hz), 6.85 (1H, dd, J=3,9 Hz), 3.75 (3H, s), 2.94 (2H, m), 2.89 (2H, m).
Step C: 6-fluoro-3,4-dihydro-2-phenyl-1(2H)-naphthalenone
The tetralone from Step B (2.8 g, 9.4 mmole) was dissolved in 45 ml of dimethylformamide. To this solution was added lithium chloride (2.0 g, 47 mmole) and water (0.42 ml, 23 mmole). The reaction mixture was heated to 150.degree. C. for 2.5 hrs and then cooled and partitioned between ether and water. The aqueous phase was separated and extracted three times with ether. The combined organic phases were washed once with water, dried (MgSO.sub.4), and concentrated (1.96 g, 87% yield). .sup.1 H NMR (CDCl.sub.3) .delta.: 8.13 (1H, dd, J=6,10 Hz), 7.31 (5H, m) 6.99 (2H, m), 3.80 (1H, m), 3.07 (2H, m), 2.43 (2H, m).
Step D: 2-(6-fluoro-1,2,3,4-tetrahydro-2-phenyl-1-naphthalenylidene)-N-[4-(trifluoromethyl)phenyl]hydrazinecarboxamide
The crude product from Step C (0.65 g, 2.7 mmole) was treated according to the procedure in Example 1, Step C. The product was obtained as a white powder (0.26 g, 2 2% yield). m.p.=158.degree.-160.degree. C. .sup.1 H NMR (CDCl.sub.3) .delta.: 8.45 (1H, s), 8.15 (1H, d, J=9 Hz), 7.98 (1H, s), 7.61 (5H, m), 7.29 (2H, m), 7.18 (2H, m), 6.92 (1H, dd, J=3,9 Hz), 6.75 (1H, d, J=3 Hz), 4.18 (1H, m), 2.64 (2H, m), 2.31 (1H, m), 2.10 (1H, m).
EXAMPLE 7
Step A: 4- Chloro-2-(2-methoxy-1-methyl-2-oxoethoxy)benzoic acid, methyl ester
A solution of methyl 4-chlorosalicylate (5.0 g) in dimethyl formamide (10 ml) was treated sequentially with methyl 3-bromopropionate (4.0 g) and potassium carbonate (6.0 g). The mixture was stirred at room temperature for 18 hrs and diluted with water. The mixture was extracted with ether and the organics were washed with water. The organic layer was dried and evaporated to give the desired material (6.7 g) as a low melting solid. NMR: 7.8 (d, 1H), 7.2 (m 1H), 6.9 (m, 1H), 4.8 (q, 1H), 3.9 (s, 3H), 3.8 (s, 3H), 1.7 (d, 3H).
Step B: 6-chloro-2-methyl-3(2H)-benzofuranone
A mixture of the compound of Example 7, Step A, (6.7 g) and sodium hydride (60% in oil, 1.5 g) was heated to reflux in tetrahydrofuran (50 ml). It Was then allowed to cool to room temperature over 1.5 hrs. The cooled mixture was treated with aqueous ammonium chloride solution and ether. The ether solution was dried over magnesium sulfate and then evaporated. The oil was subjected to chromatography on silica gel with hexanes/ethyl acetate (25:1) as the eluent. The desired product (1.99 g) was obtained as a low melting solid. NMR: 7.6 (d, 1H), 7.1 (m 2H), 4.7 (q, 1H), 1.55 (d, 3H).
Step C: (Z)-2-(6-chloro-2-methyl-3(2H)-benzofuranylidene)-N-[4-(trifluoromethyl)phenyl]hydrazinecarboxamide
The compound of Example 7, Step B, (1.9 g) was dissolved in ethanol (15 ml) and degassed with nitrogen. Then hydrazine hydrate (1.2 ml) was added and the mixture was heated at reflux for 1.5 hrs and evaporated to dryness. The residue was chromatographed on silica in hexanes/ethyl acetate (2:1). The first product eluted was the hydrazone syn to the methyl group (0.5 g). The next fraction (0.9 g) was mixed syn and anti. Pure anti hydrazone was eluted last (0.5 g). The syn hydrazone was treated with p-trifluoromethylphenylisocyanate (0.4 ml) in ether (10 ml). The desired material began to crystallize soon after mixing. The mixture was filtered and washed with ether to provide a solid (0.8 g). m.p.: 196.degree.-198.degree. C. NMR: 10.0 (br, 1H), 9.4 (br, 1H), 8.2-7.0 (m, 7H), 5.35 (m, 1H), 1.6 (d, 3H).
Step D: (E)-2-(6-cloro-2-methyl-3(2H)-benzofuranyl idene)-N-[4-(trifluoromethyl)phenyl)hydrazinecarboxamide
Treating the anti hydrazone (0.5 g) obtained in Step C with P-trifluoromethylphenylisocyanate (0.4 ml) in the same manner as in Step C resulted in the isolation of the desired product as a solid (0.8 g). m.p. - 205.degree.-207.degree. C. NMR: (10.4 (br, NH), 9.4 (br, 1H), 8.2-7.0 (m, 7H), 5.8 (m, 1H), 1.47 (d, 3H).
By the general procedures described herein and obvious modifications known to one skilled in the art, one can prepare the compounds of Tables 1 to 16. The compounds of Tables 1 through 10 are listed along with their melting points.
In Tables 1 through 16 the following notations have been used: ##STR9##
TABLE 1__________________________________________________________________________CMPD R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 m.p. .degree.C.__________________________________________________________________________ 1 CF.sub.3 5-Cl 4-ClPh H H H 214-216 2 4-Br 5-Cl 4-ClPh H H H 230-232 3 4-OMe 5-Cl 4-ClPh H H H 202-204 4 4-Cl 5-Cl 4-ClPh H H H 231-233 5 4-CF.sub.3 5-Cl Ph H H H 226-228 6 4-Br 5-Cl Ph H H H 237-238 7 4-OCF.sub.3 5-Cl Ph R H H 198-200 8 4-CF3 5-Cl 4-FPh H H H 223-225 9 4-Cl 5-Cl 4-FPh H H H 224-22610 4-Br 5-Cl 4-FPh H H H 230-23211 4-CF.sub.3 5-F 4-ClPh H H H 214-21612 4-Cl 5-F 4-ClPh H H H 218-22013 4-Br 5-F 4-ClPh H H H 223-22514 4-CF.sub.3 5-F 4-FPh H H H 224-22615 4-Cl 5-F 4-FPh H H H 212-21416 4-Br 5-F 4-FPh H H H 219-22117 4-OCF.sub.3 5-F 4-FPh H H H 201-20318 4-CF.sub.3 5-F Ph H H H 230-23219 4-Cl 5-F Ph H H H 233-23520 4-Br 5-F Ph H H H 236-23821 4-OCF.sub.3 5-F Ph H H H 187-19022 4-CF.sub.3 5-OMe Ph H H H 219-22123 4-OCF.sub.3 5-OMe Ph H H H 189-19124 4-CF.sub.3 5-OMe 4-FPh H H H 197-19925 4-CF.sub.3 5-OCH.sub.2 CF.sub.3 4-FPh H H H 217-21926 4-OCF.sub.3 5-OCH.sub.2 CF.sub.3 4-FPh H H H 204- 20627 4-CF.sub.3 5-O-i-Pr 4-FPh H H H 198-20128 4-CF.sub.3 5-OPh 4-FPh H H H 224-22629 4-CF.sub.3 5-OEt 4-FPh H H H 206-20830 4-OCF.sub.3 5-OEt 4-FPh H H H 195-19731 4-Cl H Ph H H H 220-22132 4-Br H Ph H H H 231-23233 4-CF.sub.3 H Ph H H H 223-22434 4-Cl H 4-FPh H H H 197-20135 4-CF.sub.3 5-OH Ph H H H 240-24236 4-CF.sub.3 5-Br 4-FPh H H H 218-22037 4-Br 5-Br 4-FPh H H H 227-22938 4-CF.sub.3 5-F 3-CF.sub.3Ph H H H 225-22739 4-Br 5-F 3-CF.sub.3Ph H H H 221-22340 4-CF.sub.3 5-F 2-FPh H H H 218-22041 4-Br 5-F 2-FPh H H H 231-23342 4-CF.sub.3 5-F 3-FPh H H H 210-21243 4-Br 5-F 3-FPh H H H 218-22044 4-CF.sub.3 5-F 2,4-di-FPh H H H 219-22145 4-Br 5-F 2,4-di-FPh H H H 214-21646 4-CF.sub.3 5-F 4-OEtPh H H H 184-18647 4-CF.sub.3 5-F 4-MePh H H H 219-22148 4-Br 5-F 4-MePh H H H 227-22949 4-CF.sub.3 5-F 2-naphthyl H H H 229-23050 4-Br 5-F 2-naphthyl H H H 230-23251 4-CF.sub.3 5-F 3,4-di-ClPh H H H 214-21652 4-CF.sub.3 4-F Ph H H H 214-21653 4-Br 4-F Ph H H H 222-22454 4-CF.sub.3 4-F 4-ClPh H H H 236-23855 4-OCF.sub.3 4-F 4-ClPh H H H 209-21156 2,4-di-Cl 5-Cl Ph H H H >25057 H 5-Cl Ph H H H 209-21158 4-NO.sub.2 5-Cl Ph H H H >25059 3,4-di-Cl 5-F 4-FPh H H H 132-13660 2,4-di-F 5-F 4-FPh H H H 213-21561 4-F 5-F 4-FPh H H H 216-21862 4-CF.sub.3 6-F 4-ClPh H H H 237-23963 4-Cl 6-F 4-ClPh H H H 236-23864 4-Br 6-F 4-ClPh H H H 238-24065 4-CF.sub.3 7-Cl Ph H H H 124-12566 4-CF.sub.3 4,5-di-F 4-FPh H H H 233-23567 4-OCF.sub.3 4,5-di-F 4-FPh H H H 224-22668 4-Br 4,5-di-F 4-FPh H H H 229-23169 4-CF.sub.3 5-Cl 4-ClPh Me H H 165-16970 4-Br 5-Cl 4-ClPh Me H H 149-15371 4-OMe 5-Cl 4-ClPh Me H H 187-19072 4-CF.sub.3 5-F 4-FPh Me H H 85-8973 4-Br 5-F 4-FPh Me H H 70-7474 4-CF.sub.3 5-Cl H H H H 240-24275 4-Br 5-Cl H H H H 244-24676 4-Cl 5-Cl H H H H 248-24977 4-CF.sub.3 5-Cl Me H H H 208-21078 4-Cl 5-Cl Me H H H 221-22379 4-Br 5-Cl Me H H H 228-23080 4-CF.sub.3 7-Cl Me H H H >25081 4-CF.sub.3 5-F Me H H H 218-22082 4-Cl 5-F Me H H H 219-22183 4-Br 5-F Me H H H 224-22684 4-CF.sub.3 5-OMe Et H H H 191-19385 4-OCF.sub.3 5-OMe Et H H H 178-18086 4-CF.sub. 3 5-Cl CO.sub.2 Me H H H 242-24487 4-CF.sub.3 5-F CO.sub.2 Me H H H 238-24088 4-CF.sub.3 5-Cl CO.sub.2 Me Me H H 192-19489 4-CF.sub.3 5-F CO.sub.2 Me Me H H 203-20590 4-CF.sub.3 5-Cl i-Pr H H H 216-21891 4-OCF.sub.3 5-Cl i-Pr H H H 204-20692 4-CF.sub.3 5-OCH.sub.2 CF.sub.3 Me H H H 212-21493 4-OCF.sub.3 5-OCH.sub.2 CF.sub.3 Me H H H 189-19194 4-Cl 5-OCH.sub.2 CF.sub.3 Me H H H 220-22295 4-CF.sub.3 5-Cl Me Me H H 215-21796 4-Br 5-Cl Me Me H H 214-21697 4-Cl 5-Cl Me Me H H 203-20598 4-CF.sub.3 5-F i-Pr H H H 216-22099 4-Br 5-F i-Pr H H H 217-222100 4-CF.sub.3 5-F H H H H >245101 4-Cl 5-F H H H H 240-242102 4-Br 5-F H H H H >245103 4-CF.sub.3 5-F 4-FPh H C(O)Me H oil104 4-OCF.sub.3 5-F 4-FPh H C(O)Me H oil105 4-CF.sub.3 5-F 4-FPh H CO.sub.2 Me H oil106 4-CF.sub.3 5-F 2,4-di-Ph H CO.sub.2 Me H oily solid107 4-CF.sub.3 5-F 4-FPh H CO.sub.2 Et H 144-146108 4-Br H 4-FPh H H H 204-207109 4-CF.sub.3 H 4-FPh H H H 212-213110 4-Cl 4-Cl Ph H H H 234-239111 4-Br 4-Cl Ph H H H 283-285112 4-CF.sub.3 4-Cl Ph H H H 205-209113 4-CF.sub.3 5-Me 4-ClPh H H H 210-214114 4-Br 5-Me 4-ClPh H H H 260-262115 4-Cl 5-Me 4-ClPh H H H 270-272116 4-CF.sub.3 4-Cl 4-FPh H H H wax117 4-Br 4-Cl 4-FPh H H H wax118 4-Cl 4-Cl 4-FPh H H H wax119 4-CF.sub.3 5-F CH.sub.2 Ph-4-F CH.sub.2 Ph-4-F H H 76-81120 4-Cl 5-F CH.sub.2 Ph-4-F CH.sub.2 Ph-4-F H H 84-89__________________________________________________________________________
TABLE 2______________________________________ ##STR10##CMPD R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 m.p. .degree.C.______________________________________121 4-Br 5-Cl Ph H H H 209-210122 4-CF.sub.3 5-Cl Ph H H H 217-218123 4-Cl 5-Cl 4-BrPh H H H 236-238124 4-Br 5-Cl 4-BrPh H H H 248-250125 4-CF.sub.3 5-Cl 4-BrPh H H H 245-247126 4-Cl 5-Cl 4-OMePh H H H 209-210127 4-Br 5-Cl 4-OMePh H H H 216-217128 4-CF.sub.3 5-Cl 4-OMePh H H H 226-228129 4-Cl 5-Cl Me H H H 236-238130 4-Br 5-Cl Me H H H 230-235131 4-CF.sub.3 5-Cl Me H H H 234-235132 4-CF.sub.3 5-Cl CO.sub.2 Me H H H 220-222133 4-Br 5-Cl 4-FPh H H H 221-222134 4-CF.sub.3 5-Cl 4-FPh H H H 233-234135 4-CF.sub.3 5-Cl H H Me H 114-117136 4-Cl 4-F Me H H H 233-236137 4-Br 4-F Me H H H 236-239138 4-CF.sub.3 4-F Me H H H 235-237139 4-Cl 5-F Ph H H H 179-184140 4-Br 5-F Ph H H H 185-192141 4-CF.sub.3 5-F Ph H H H 158-160142 4-CF.sub.3 4-F CO.sub.2 Me H H H 203-204143 4-CF.sub.3 5-F 4-FPh H H H 179-180144 4-CF.sub.3 5-F 4-ClPh H H H 225-230145 4-Cl 5-F Me H H H 200-210146 4-Br 5-F Me H H H 196-198147 4-CF.sub.3 5-F Me H H H 195-198148 4-CF.sub.3 H CO.sub.2 Me H H H 207-208149 4-CF.sub.3 H CO.sub.2 Me H Me H oil150 4-CF.sub.3 H H H H H 230-232151 4-CF.sub.3 H 4-ClPh H H H 228-230152 4-OMe H 4-ClPh H H H 191-193153 4-F H 4-ClPh H H H 204-205154 3-CF.sub.3 H 4-ClPh H H H 199-200155 3-CO.sub.2 Et H 4-ClPh H H H 205-206156 4-F,3-Cl H 4-ClPh H H H 210-212157 4-CF.sub.3 5-Br H H H H 253-255158 4-CF.sub.3 5-F H H H H 257-259______________________________________
TABLE 3______________________________________ ##STR11##CMPD R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 m.p. .degree.C.______________________________________159 4-CF.sub.3 5-Cl H H H H 224-225160 4-Cl 5-Cl H H H H 211-213161 4-Br 5-Cl H H H H 210-213162 4-CF.sub.3 5-Cl Me H H H 174-176______________________________________
TABLE 4______________________________________ ##STR12##CMPD R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 A m.p. .degree.C.______________________________________163 4-Cl H Me Me H H O 177-182164 4-CF.sub.3 H Me Me H H O 186-188165 4-CF.sub.3 5-Cl Me Me H H O 214-217166 4-Cl 5-Cl Me Me H H O 204-207167 4-Br 5-Cl Me Me H H O 204-208168 4-CF.sub.3 4-F Me Me H H O 203-206169 4-Cl 4-F Me Me H H O 193-196170 4-Br 4-F Me Me H H O 194-198171 4-CF.sub.3 5-Cl Me 4- H H O 219-220 FPh172 4-Cl 5-Cl Me 4- H H O 209-211 FPh173 4-CF.sub.3 H Me Ph H H O 174-176174 4-Cl H Me Ph H H O 165-167175 4-Br H Me Ph H H O 165-166176 4-CF.sub.3 5-Cl Me Et H H O 190-192177 4-CF.sub.3 5-Cl Me allyl H H O 150-152178 4-Cl 5-Cl Me allyl H H O 142-145179 4-CF.sub.3 5-CF.sub.3 Me Me H H O 234-236180 4- 5-CF.sub.3 Me Me H H O 196-199 OCF.sub.3181 4- 5-Cl Me allyl H H O 128-130 OCF.sub.3182 4-Cl H Me Me Me Me O 155-158183 4-Cl H Me Me Me H O wax184 4-CF.sub.3 H Ph Me Me Me O 128-130185 4-CF.sub.3 H Me Me H H S 193-197186 4-Cl H Me Me Me Me S 192-193______________________________________
TABLE 5______________________________________ ##STR13##CMPD R.sub.1 R.sub.2 R.sub.3 R.sub.4 syn/anti m.p. .degree.C.______________________________________187 4-CF.sub.3 H Me H syn 179-180188 4-CF.sub.3 H Me H anti 212-213189 4-CF.sub.3 5-Cl Me H syn 196-198190 4-CF.sub.3 5-Cl Me H anti 205-207191 4-Br H Me H mix 193-196192 4-Br 5-Cl Me H mix 195-200193 4-CF.sub.3 H i-Pr H syn 201-202194 4-CF.sub.3 H i-Pr H anti 181-183195 4-Cl H i-Pr H syn 151-153196 4-Cl H i-Pr H mix 203-205197 4-Br H i-Pr H mix 200-205198 4-CF.sub.3 5-Cl i-Pr H syn 195-196199 4-Br 5-Cl i-Pr H mix 197-199200 4-Cl 5-Cl i-Pr H anti 192-196201 4-CF.sub.3 5-Cl i-Pr H mix 196-200______________________________________
TABLE 6______________________________________ ##STR14##CMPD R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 m.p. .degree.C.______________________________________202 4-CF.sub.3 5-F 4-FPh H H H 192-194203 4-CF.sub.3 5-F Ph H H H 154-156204 4-Cl 5-F 4-FPh H H H 182-184205 4-Br 5-Cl Ph H H H 192-194______________________________________
TABLE 7______________________________________ ##STR15##CMPD R.sub.1 R.sub.2 R.sub.3 R.sub.a R.sub.b m.p. .degree.C.______________________________________206 4-CF.sub.3 5-F 4-FPh Me H 218-220207 4-CF.sub.3 5-Cl H i-Pr H 238-240208 4-CF.sub.3 5-F H Me H 241-243209 4-OCF.sub.3 5-F H Me H 211-213210 4-CF.sub.3 H H Me Me 222-223211 4-Cl H H Me Me 215-216212 4-CF.sub.3 5-F H Me Me 198-201213 4-F 5-F H Me Me 201.5-205214 4-CF.sub.3 H H Ph H 248.5-250215 4-Cl H H Ph H 253-254216 4-CF.sub.3 H H Ph Me 207-209217 4-Cl H H Ph Me 203-205218 4-CF.sub.3 H H 4-ClPh H 243.5-245219 4-Cl H H 4-ClPh H 242.5-244220 4-CF.sub.3 5-Cl H Ph H 246-248221 4-5r 5-Cl H Ph H 256-258222 4-CF.sub.3 5-Cl H 4-ClPh H 235-238223 4-Br 5-Cl H 4-ClPh H 260-262224 4-CF.sub.3 H H 4-FPh H 253-255225 4-Cl H H 4-FPh H 249-250226 4-F H H 4-FPh H 244-246227 4-CF.sub.3 5-F H Ph H >250228 4-Cl 5-F H Ph H >250229 4-CF.sub.3 4-Cl H 4-FPh H 252.5-253230 4-Cl 4-Cl H 4-FPh H 260-261231 4-CF.sub.3 4-Cl H 4-FPh Me 176-179232 4-CF.sub.3 4-F H 4-FPh H 242-244233 4-Cl 4-F H 4-FPh H 248-250______________________________________
TABLE 8______________________________________ ##STR16##CMPD R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 A m.p. .degree.C.______________________________________234 4-Cl 5-Cl Ph H H O 180-182235 4-Br 5-Cl Ph H H O 189-191236 4-CF.sub.3 5-Cl Ph H H O 211-212237 4-Cl 5-Cl 4-FPh H H O 171-173238 4-Br 5-Cl 4-FPh H H O 187-189239 4-CF.sub.3 5-Cl 4-FPh H H O 180-185240 4-CF.sub.3 5-F Ph H H O 197-200241 4-Br 5-F 4-FPh H H O glass242 4-CF.sub.3 5-F 4-FPh H H O glass243 4-Cl 5-Cl 4-FPh H H S 216-218244 4-Br 5-Cl 4-FPh H H S 219-221245 4-CF.sub.3 5-Cl 4-FPh H H S >220246 4-Cl 5-Cl Ph H H S 194-196247 4-Br 5-Cl Ph H H S 210-212248 4-CF.sub.3 5-Cl Ph H H S 205-208249 4-Cl 5-Cl 4-ClPh H H S 184-186250 4-Br 5-Cl 4-ClPh H H S 199-201251 4-CF.sub.3 5-Cl 4-ClPh H H S 207-210252 4-Cl 4-F 4-FPh H H S 216-218253 4-Br 4-F 4-FPh H H S 218-220254 4-CF.sub.3 4-F 4-FPh H H S 217-219255 4-Cl 4-F Ph H H S 195-197256 4-CF.sub.3 4-F Ph H H S 208-210257 4-Cl 5-F 4-FPh H H S 209-211258 4-Br 5-F 4-FPh H H S 215-217259 4-CF.sub.3 5-F 4-FPh H H S 202-204260 4-CF.sub.3 H H H H C(Me).sub.2 206-210261 4-Cl H H H H C(Me).sub.2 208-212262 4-OMe H H H H C(Me).sub.2 177- 180263 4-CF.sub.3 H H H H S 230-235______________________________________
TABLE 9______________________________________ ##STR17##CMPD R.sub.1 R.sub.2 R.sub.3 R.sub.5 R.sub.c R.sub.d A m.p. .degree.C.______________________________________264 4-CF.sub.3 5-Cl H H Me Me S 151-153265 4-CF.sub.3 5-Cl H Me Me H S >250266 4-CF.sub.3 5-Cl H H H Me S 234-235267 4-CF.sub.3 5-Cl H H Me Me O 253-255______________________________________
TABLE 10______________________________________ ##STR18##CMPD O V A R.sub.2 R.sub.3 R.sub.4 m.p. .degree.C.______________________________________268 Q-5 -- CH.sub.2 CH.sub.2 H H H 173-174269 Q-6 S CH.sub.2 CH.sub.2 H H H 248-249______________________________________
TABLE 11______________________________________ ##STR19##R.sub.1 R.sub.2 R.sub.4 R.sub.10 A______________________________________4-F 4-F H H CH.sub.24-Cl 4-F H H CH.sub.24-OCF.sub.3 4-F H H CH.sub.24-OCF.sub.2 H 4-F H H CH.sub.23,4-di-Cl 4-F H H CH.sub.24-CN 4-Cl H H CH.sub.24-CO.sub.2 Me 4-Cl H H CH.sub.24-OCF.sub.2 H 4-Cl H H CH.sub.24-OCF.sub.3 4-Cl H H CH.sub.24-F 5-F H H CH.sub.24-OCF.sub.2 H 5-F H R CH.sub.24-OCF.sub.2 CF.sub.2 H 5-F H H CH.sub.24-NO.sub.2 5-F H H CH.sub.24-SCF.sub.2 H 5-F H H CH.sub.24-CN 5-F H H CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-F H H CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-F H H CH.sub.24-F 5-Cl H H CH.sub.34-Cl 5-Cl H H CH.sub.24-OCF.sub.2 H 5-Cl H H CH.sub.24-NO.sub.2 5-Cl H N CH.sub.24-SCF.sub.2 H 5-Cl H H CH.sub.24-CN 5-Cl H E CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl H H CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl H H CH.sub.24-Cl 5-Br H H CH.sub.24-Br 5-Br H N CH.sub.24-CF.sub.3 5-Br H H CH.sub.24-OCF.sub.2 H 5-Br H H CH.sub.24-OCF.sub.3 5-Br H H CH.sub.24-Cl 5-CN H H CH.sub.24-Br 5-CN H H CH.sub.24-CF.sub.3 5-CN H H CH.sub.24-OCF.sub.2 H 5-CN H H CH.sub.24-OCF.sub.3 5-CN H H CH.sub.24-Cl 5-OMe H H CH.sub.24-Br 5-OMe H H CH.sub.24-CF.sub.3 5-CF.sub.3 H H CH.sub.24-Cl 5-CF.sub.3 H H CH.sub.24-Br 5-CF.sub.3 H H CH.sub.24-OCF.sub.3 5-CF.sub.3 H H CH.sub. 24-OCF.sub.2 H 5-CF.sub.3 H H CH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H H H CH.sub.24-OCF.sub.3 5-OCF.sub.2 H H H CH.sub.24-CF.sub.3 5-OCF.sub.2 H H H CH.sub.24-Cl 5-OCF.sub.2 H H H CH.sub.24-Br 5-OCF.sub.2 H H H CH.sub.24-OCF.sub.2 H 5-OCF.sub.3 H H CH.sub.24-OCF.sub.3 5-OCF.sub.3 H H CH.sub.24-CF.sub.3 5-OCF.sub.3 H H CH.sub.24-Cl 5-OCF.sub.3 H H CH.sub.24-Br 5-OCF.sub.3 H H CH.sub.24-OCF.sub.2 H 5-OPh H H CH.sub.24-OCF.sub.3 5-OPh H H CH.sub.24-CF.sub.3 5-OPh H H CH.sub.24-Cl 5-OPh H H CH.sub.24-Br 5-OPh H H CH.sub.24-CF.sub.3 5-SMe H H CH.sub.24-Cl 5-SMe H H CH.sub.24-Br 5-SMe H H CH.sub.24-CF.sub.3 6-F H H CH.sub.24-Cl 6-F H H CH.sub.24-Br 6-F H H CH.sub.24-CF.sub.3 6-Cl H H CH.sub.24-Cl 6-Cl H H CH.sub.24-Br 6-Cl H H CH.sub.24-SCF.sub.2 H 5-F H 4-F CH.sub.24-F 5-F H 4-F CH.sub.24-CN 5-F H 4-F CH.sub.24-OCF.sub.2 CF.sub.2 H 5-F H 4-F CH.sub.24-OCF.sub.3 5-F H 4-F CH.sub.23,4-di-Cl 5-F H 4-F CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-F H 4-F CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-F H 4-F CH.sub.24-OCF.sub.2 H 5-F H 4-Cl CH.sub.24-OCF.sub.3 5-F H 4-Cl CH.sub.24-Cl 5-F H 4-NO.sub.2 CH.sub.24-Br 5-F H 4-NO.sub.2 CH.sub.24-CF.sub.3 5-F H 4-NO.sub.2 CH.sub.24-OCF.sub.2 H 5-F H 4-NO.sub.2 CH.sub.24-OCF.sub.3 5-F H 4-NO.sub.2 CH.sub.24-Cl 5-F H 4-CN CH.sub.24-Br 5-F H 4-CN CH.sub.24-CF.sub.3 5-F H 4-CN CH.sub.24-OCF.sub.2 H 5-F H 4-CN CH.sub.24-OCF.sub.3 5-F H 4-CN CH.sub.24-Cl 5-F H 4-OMe CH.sub.24-Br 5-F H 4-OMe CH.sub.24-CF.sub.3 5-F H 4-OMe CH.sub.24-OCF.sub.2 H 5-F H 4-OMe CH.sub.24-OCF.sub.3 5-F H 4-OMe CH.sub.24-Cl 5-F H 4-CF.sub.3 CH.sub.24-Br 5-F H 4-CF.sub.3 CH.sub.24-CF.sub.3 5-F H 4-CF.sub.3 CH.sub.24-OCF.sub.3 5-F H 4-CF.sub.3 CH.sub.24-OCF.sub. 2 H 5-F H 4-CF.sub.3 CH.sub.24-CF.sub.3 5-F H 4-OCF.sub.2 H CH.sub.24-Cl 5-F H 4-OCF.sub.2 H CH.sub.24-Br 5-F H 4-OCF.sub.2 H CH.sub.24-OCF.sub.2 H 5-F H 4-OCF.sub.2 H CH.sub.24-OCF.sub.3 5-F H 4-OCF.sub.2 H CH.sub.24-OCF.sub.2 CF.sub.2 H 5-Cl H 4-F CH.sub.24-F 5-Cl H 4-F CH.sub.24-OCF.sub.3 5-Cl H 4-F CH.sub.24-OCF.sub.2 H 5-Cl H 4-F CH.sub.24-NO.sub.2 5-Cl H 4-F CH.sub.23,4-di-Cl 5-Cl H 4-F CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl H 4-F CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl H 4-F CH.sub.24-OCF.sub.3 5-Cl H 4-Cl CH.sub.24-OCF.sub.2 H 5-Cl H 4-Cl CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl H 4-Cl CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl B 4-Cl CH.sub.24-CN 5-Cl H 4-Cl CH.sub.24-F 5-Cl H 4-Cl CH.sub.24-NO.sub.2 5-Cl H 4-Cl CH.sub.2H 5-Cl H 4-Cl CH.sub.24-CF.sub.3 5-CF.sub.3 H 4-F CH.sub.24-OCF.sub.3 5-CF.sub.3 H 4-F CH.sub.24-Cl 5-CF.sub.3 H 4-F CH.sub.24-Br 5-CF.sub.3 H 4-F CH.sub.24-OCF.sub.2 H 5-CF.sub.3 H 4-F CH.sub.24-CF.sub.3 5-CF.sub.3 H 4-Cl CH.sub.24-OCF.sub.3 5-CF.sub.3 H 4-Cl CH.sub.24-Cl 5-CF.sub.3 H 4-Cl CH.sub.24-Br 5-CF.sub.3 H 4-Cl CH.sub.24-OCF.sub.2 H 5-CF.sub.3 H 4-Cl CH.sub.24-CF.sub.3 5-OCF.sub.2 H H 4-F CH.sub.24-Cl 5-OCF.sub.2 H H 4-F CH.sub.24-Br 5-OCF.sub.2 H H 4-F CH.sub.24-OCF.sub.3 5-OCF.sub.2 H H 4-F CH.sub.24-CF.sub.3 5-OCF.sub.2 H H 4-Cl CH.sub.24-Cl 5-OCF.sub.2 H H 4-Cl CH.sub.24-Br 5-OCF.sub.2 H H 4-Cl CH.sub.24-OCF.sub.3 5-OCF.sub.2 H H 4-Cl CH.sub.24-CF.sub.3 4-F H 4-F CH.sub.24-Cl 4-F H 4-F CH.sub.24-Br 4-F H 4-F CH.sub.24-OCF.sub.3 4-F H 4-F CH.sub.24-CF.sub.3 4-F H 4-Cl CH.sub.24-Cl 4-F H 4-Cl CH.sub.24-Br 4-F H 4-Cl CH.sub.24-CF.sub.3 4-Cl H 4-Cl CH.sub.24-Cl 4-Cl H 4-Cl CH.sub.24-Br 4-Cl H 4-Cl CH.sub.24-OCF.sub.3 4-Cl H 4-Cl CH.sub.24-CF.sub.3 4-Cl H 4-F CH.sub.24-Cl 4-Cl H 4-F CH.sub.24-Br 4-Cl H 4-F CH.sub.24-OCF.sub.3 4-Cl H 4-F CH.sub.24-CF.sub.3 5-Cl H 4-CF.sub.3 CH.sub.24-Cl 5-Cl H 4-CF.sub.3 CH.sub.24-Br 5-Cl H 4-CF.sub.3 CH.sub.24-OCF.sub.3 5-Cl H 4-CF.sub.3 CH.sub.24-OCF.sub.2 H 5-Cl H 4-CF.sub.3 CH.sub.24-CF.sub.3 5-Cl H 4-SMe CH.sub.24-Cl 5-Cl H 4-SMe CH.sub.24-Br 5-Cl H 4-SMe CH.sub.24-OCF.sub.3 5-Cl H 4-SMe CH.sub.24-CF.sub.3 5-Cl H 4-NO.sub.2 CH.sub.24-Cl 5-Cl H 4-NO.sub.2 CH.sub.24-Br 5-Cl H 4-NO.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl H 4-NO.sub.2 CH.sub.24-CF.sub.3 5-Cl H 4-OMe CH.sub.24-Cl 5-Cl H 4-OMe CH.sub.24-Br 5-Cl H 4-OMe CH.sub.24-OCF.sub.2 H 5-Cl H 4-OMe CH.sub.24-CF.sub.3 5-Cl H 4-OPh CH.sub.24-Cl 5-Cl H 4-OPh CH.sub.24-Br 5-Cl H 4-OPh CH.sub.24-OCF.sub.2 H 5-Cl H 4-OPh CH.sub.24-CF.sub.3 5-Cl H 4-CN CH.sub.24-Cl 5-Cl H 4-CN CH.sub.24-Br 5-Cl H 4-CN CH.sub.24-OCF.sub.2 H 5-Cl H 4-CN CH.sub.24-CF.sub.3 5-Cl H 4-CO.sub.2 Me CH.sub.24-Cl 5-Cl H 4-CO.sub.2 Me CH.sub.24-Br 5-Cl H 4-CO.sub.2 Me CH.sub.24-CF.sub.3 H Me H CH.sub.24-Cl H Me H CH.sub.24-Br H Me H CH.sub.24-OCF.sub.2 H H Me H CH.sub.24-OCF.sub.3 H Me H CH.sub.24-CF.sub.3 4-F Me H CH.sub.24-Cl 4-F Me H CH.sub.24-Br 4-F Me H CH.sub.24-OCF.sub.2 H 4-F Me H CH.sub.24-OCF.sub.3 4-F Me H CH.sub.24-CF.sub.3 4-Cl Me H CH.sub.24-Cl 4-Cl Me H CH.sub.24-Br 4-Cl Me H CH.sub.24-OCF.sub.2 H 4-Cl Me H CH.sub.24-OCF.sub.2 H 4-Cl Me H CH.sub.24-CF.sub.3 5-F Me H CH.sub.24-Cl 5-F Me H CH.sub.24-Br 5-F Me H CH.sub.24-OCF.sub.2 H 5-F Me H CH.sub.24-CF.sub.3 5-Cl Me H CH.sub.24-Cl 5-Cl Me H CH.sub.24-Br 5-Cl Me H CH.sub.24-OCF.sub.2 H 5-Cl Me H CH.sub.24-CF.sub.3 4-F Me 4-F CH.sub.24-Cl 4-F Me 4-F CH.sub.24-Br 4-F Me 4-F CH.sub.24-OCF.sub.2 H 4-F Me 4-F CH.sub.24-CF.sub.3 4-Cl Me 4-F CH.sub.24-Cl 4-Cl Me 4-F CH.sub.24-Br 4-Cl Me 4-F CH.sub.24-OCF.sub.2 H 4-Cl Me 4-F CH.sub.24-CF.sub.3 5-F Me 4-F CH.sub.24-Cl 5-F Me 4-F CH.sub.24-Br 5-F Me 4-F CH.sub.24-OCF.sub.2 H 5-F He 4-F CH.sub.24-CE3 5-Cl Me 4-F CH.sub.24-Cl 5-Cl Me 4-F CH.sub.24-Br 5-Cl Me 4-F CH.sub.24-OCF.sub.2 H 5-Cl Me 4-F CH.sub.24-CF.sub.3 4-F Me 4-Cl CH.sub.24-Cl 4-F Me 4-Cl CH.sub.24-Br 4-F Me 4-Cl CH.sub.24-OCF.sub.2 H 4-F Me 4-Cl CH.sub.24-CF.sub.3 4-Cl Me 4-Cl CH.sub.24-Cl 4-Cl Me 4-Cl CH.sub.24-Br 4-Cl Me 4-Cl CH.sub.24-OCF.sub.2 H 4-Cl Me 4-Cl CH.sub.24-CF.sub.3 5-F Me 4-Cl CH.sub.24-Cl 5-F Me 4-Cl CH.sub.24-Br 5-F Me 4-Cl CH.sub.24-OCF.sub.2 H 5-F Me 4-Cl CH.sub.24-CF.sub.3 5-Cl Me 4-Cl CH.sub.24-Cl 5-Cl Me 4-Cl CH.sub.24-Br 5-Cl Me 4-Cl CH.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl CH.sub.24-CF.sub.3 5-Cl Me 4-Cl CH.sub.24-Cl 5-Cl Me 4-Cl CH.sub.24-Br 5-Cl Me 4-Cl CH.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl CH.sub.24-CF.sub.3 5-Cl Et 4-F CH.sub.24-Cl 5-Cl Et 4-F CH.sub.24-Br 5-Cl Et 4-F CH.sub.24-CF.sub.3 5-Cl Et 4-Cl CH.sub.24-Cl 5-Cl Et 4-Cl CH.sub.24-Br 5-Cl Et 4-Cl CH.sub.24-CF.sub.3 5-Cl allyl 4-F CH.sub.24-Cl 5-Cl allyl 4-F CH.sub.24-Br 5-Cl allyl 4-F CH.sub.24-CF.sub.3 5-Cl allyl 4-Cl CH.sub.24-Cl 5-Cl allyl 4-Cl CH.sub.24-Br 5-Cl allyl 4-Cl CH.sub.24-CF.sub.3 5-Cl propargyl 4-F CH.sub.24-Cl 5-Cl propargyl 4-F CH.sub.24-Br 5-Cl propargyl 4-F CH.sub.24-CF.sub.3 5-Cl propargyl 4-Cl CH.sub.24-Cl 5-Cl propargyl 4-Cl CH.sub.24-Br 5-Cl propargyl 4-Cl CH.sub.24-CF.sub.3 5-F H 4-F O4-OCF.sub.3 5-F H 4-F O4-CF.sub.3 4-F H 4-F O4-OCF.sub.3 4-F H 4-F O4-CF.sub.3 5-Cl H 4-F O4-OCF.sub.3 5-Cl H 4-F O4-CF.sub.3 5-CF.sub.3 H 4-F O4-OCF.sub.3 5-CF.sub.3 H 4-F O4-CF.sub.3 5-F H 4-F S4-OCF.sub.3 5-F H 4-F S4-CF.sub.3 4-F H 4-F S4-OCF.sub.3 4-F H 4-F S4-CF.sub.3 5-Cl H 4-F S4-OCF.sub.3 5-Cl H 4-F S4-CF.sub.3 5-CF.sub.3 H 4-F S4-OCF.sub.3 5-CF.sub.3 H 4-F S4-CF.sub.3 H Me H O4-Cl H Me H O4-Br H Me H O4-OCF.sub.2 H H Me H O4-OCF.sub.3 H Me H O4-CF.sub.3 4-F Me H O4-Cl 4-F Me H O4-Br 4-F Me H O4-OCF.sub.2 H 4-F Me H O4-OCF.sub.3 4-F Me H O4-CF.sub.3 4-Cl Me H O4-Cl 4-Cl Me H O4-Br 4-Cl Me H O4-OCF.sub.2 H 4-Cl Me H O4-OCF.sub.3 4-Cl Me H O4-CF.sub.3 5-F Me H O4-Cl 5-F Me H O4-Br 5-F Me H O4-OCF.sub.2 H 5-F Me H O4-CF.sub.3 5-Cl Me H O4-Cl 5-Cl Me H O4-Br 5-Cl Me H O4-OCF.sub.3 5-Cl Me H O4-OCF.sub.2 H 5-Cl Me H O4-CF.sub.3 4-F Me 4-F O4-Cl 4-F Me 4-F O4-Br 4-F Me 4-F O4-OCF.sub.3 4-F Me 4-F O4-OCF.sub.2 H 4-F Me 4-F O4-CF.sub.3 4-Cl Me 4-F O4-Cl 4-Cl Me 4-F O4-Br 4-Cl Me 4-F O4-OCF.sub.3 4-Cl Me 4-F O4-OCF.sub.2 H 4-Cl Me 4-F O4-CF.sub.3 5-F Me 4-F O4-Cl 5-F Me 4-F O4-Br 5-F Me 4-F O4-OCF.sub.3 5-F Me 4-F O4-OCF.sub.2 H 5-F Me 4-F O4-CF.sub.3 5-Cl Me 4-F O4-Cl 5-Cl Me 4-F O4-Br 5-Cl Me 4-F O4-OCF.sub.3 5-Cl Me 4-F O4-OCF.sub.2 H 5-Cl Me 4-F O4-CF.sub.3 4-F Me 4-Cl O4-Cl 4-F Me 4-Cl O4-Br 4-F Me 4-Cl O4-OCF.sub.3 4-F Me 4-Cl O4-OCF.sub.2 H 4-F Me 4-Cl O4-CF.sub.3 4-Cl Me 4-Cl O4-Cl 4-Cl Me 4-Cl O4-Br 4-Cl Me 4-Cl O4-OCF.sub.3 4-Cl Me 4-Cl O4-OCF.sub.2 H 4-Cl Me 4-Cl O4-CF.sub.3 5-F Me 4-Cl O4-Cl 5-F Me 4-Cl O4-Br 5-F Me 4-Cl O4-OCF.sub.3 5-F Me 4-Cl O4-OCF.sub.2 H 5-F Me 4-Cl O4-CF.sub.3 5-Cl Me 4-Cl O4-Cl 5-Cl Me 4-Cl O4-Br 5-Cl Me 4-Cl O4-OCF.sub.2 H 5-Cl Me 4-Cl O4-OCF.sub. 3 5-Cl Me 4-Cl O4-CF.sub.3 5-Cl Me 4-Cl O4-Cl 5-Cl Me 4-Cl O4-Br 5-Cl Me 4-Cl O4-OCF.sub.3 5-Cl Me 4-Cl O4-OCF.sub.2 H 5-Cl Me 4-Cl O4-CF.sub.3 5-Cl Et 4-F O4-Cl 5-Cl Et 4-F O4-Br 5-Cl Et 4-F O4-CF.sub.3 5-Cl Et 4-Cl O4-Cl 5-Cl Et 4-Cl O4-Br 5-Cl Et 4-Cl O4-CF.sub.3 5-Cl allyl 4-F O4-Cl 5-Cl allyl 4-F O4-Br 5-Cl allyl 4-F O4-CF.sub.3 5-Cl allyl 4-Cl O4-Cl 5-Cl allyl 4-Cl O4-Br 5-Cl allyl 4-Cl O4-CF.sub.3 5-Cl propargyl 4-F O4-Cl 5-Cl propargyl 4-F O4-Br 5-Cl propargyl 4-F O4-CF.sub.3 5-Cl propargyl 4-Cl O4-Cl 5-Cl propargyl 4-Cl O4-Br 5-Cl propargyl 4-Cl O4-CF.sub.3 H Me H S4-Cl H Me H S4-Br H Me H S4-OCF.sub.2 H H Me H S4-OCF.sub.3 H Me H S4-CF.sub.3 4-F Me H S4-Cl 4-F Me H S4-Br 4-F Me H S4-OCF.sub.2 H 4-F Me H S4-OCF.sub.3 4-F Me H S4-CF.sub.3 4-Cl Me H S4-Cl 4-Cl Me H S4-Br 4-Cl Me H S4-OCF.sub.2 H 4-Cl Me H S4-OCF.sub.3 4-Cl Me H S4-CF.sub.3 5-F Me H S4-Cl 5-F Me H S4-Br 5-F Me H S4-OCF.sub.2 H 5-F Me H S4-CF.sub.3 5-Cl Me H S4-Cl 5-Cl Me H S4-Br 5-Cl Me H S4-OCF.sub.2 H 5-Cl Me H S4-CF.sub.3 4-F Me 4-F S4-Cl 4-F Me 4-F S4-Br 4-F Me 4-F S4-OCF.sub.2 H 4-F Me 4-F S4-CF.sub.3 4-Cl Me 4-F S4-Cl 4-Cl Me 4-F S4-Br 4-Cl Me 4-F S4-OCF.sub.2 H 4-Cl Me 4-F S4-CF.sub.3 5-F Me 4-F S4-Cl 5-F Me 4-F S4-Br 5-F Me 4-F S4-OCF.sub.2 H 5-F Me 4-F S4-CF.sub.3 5-Cl Me 4-F S4-Cl 5-Cl Me 4-F S4-Br 5-Cl Me 4-F S4-OCF.sub.2 H 5-Cl Me 4-F S4-CF.sub.3 4-F Me 4-Cl S4-Cl 4-F Me 4-Cl S4-Br 4-F Me 4-Cl S4-OCF.sub.2 H 4-F Me 4-Cl S4-CF.sub.3 4-Cl Me 4-Cl S4-Cl 4-Cl Me 4-Cl S4-Br 4-Cl Me 4-Cl S4-OCF.sub.2 H 4-Cl Me 4-Cl S4-CF.sub.3 5-F Me 4-Cl S4-Cl 5-F Me 4-Cl S4-Br 5-F Me 4-Cl S4-OCF.sub.2 H 5-F Me 4-Cl S4-CF.sub.3 5-Cl Me 4-Cl S4-Cl 5-Cl Me 4-Cl S4-Br 5-Cl Me 4-Cl S4-OCF.sub.2 H 5-Cl Me 4-Cl S4-CF.sub.3 5-Cl Me 4-Cl S4-Cl 5-Cl Me 4-Cl S4-Br 5-Cl Me 4-Cl S4-OCF.sub.2 H 5-Cl Me 4-Cl S4-CF.sub.3 5-Cl Et 4-F S4-Cl 5-Cl Et 4-F S4-Br 5-Cl Et 4-F S4-CF.sub.3 5-Cl Et 4-Cl S4-Cl 5-Cl Et 4-Cl S4-Br 5-Cl Et 4-Cl S4-CF.sub.3 5-Cl allyl 4-F S4-Cl 5-Cl allyl 4-F S4-Br 5-Cl allyl 4-F S4-CF.sub.3 5-Cl allyl 4-Cl S4-Cl 5-Cl allyl 4-Cl S4-Br 5-Cl allyl 4-Cl S4-CF.sub.3 5-Cl propargyl 4-F S4-Cl 5-Cl propargyl 4-F S4-Br 5-Cl propargyl 4-F S4-CF.sub.3 5-Cl propargyl 4-Cl S4-Cl 5-Cl propargyl 4-Cl S4-Br 5-Cl propargyl 4-Cl S4-Cl H H H CH.sub.2 CH.sub.24-OCF.sub.3 H H H CH.sub.2 CH.sub.24-F 4-F H H CH.sub.2 CH.sub.24-Cl 4-F H H CH.sub.2 CH.sub.24-Br 4-F H H CH.sub.2 CH.sub.24-CF.sub.3 4-F H H CH.sub.2 CH.sub.24-OCF.sub.3 4-F H H CH.sub.2 CH.sub.24-OCF.sub.2 H 4-F H H CH.sub.2 CH.sub.23,4-di-Cl 4-F H H CH.sub.2 CH.sub.24-CN 4-Cl H H CH.sub.2 CH.sub.24-CO.sub.2 Me 4-Cl H H CH.sub.2 CH.sub.24-Cl 4-Cl H H CH.sub.2 CH.sub.24-Br 4-Cl H H CH.sub.2 CH.sub.24-CF.sub.3 4-Cl H H CH.sub.2 CH.sub.24-OCF.sub.2 H 4-Cl H H CH.sub.2 CH.sub.24-OCF.sub.3 4-Cl H H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F H H CH.sub.2 CH.sub.24-OCF.sub.3 5-F H H CH.sub.2 CH.sub.24-NO.sub.2 5-F H H CH.sub.2 CH.sub.24-SCF.sub.2 H 5-F H H CH.sub.2 CH.sub.24-CN 5-F H H CH.sub.2 CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-F H H CH.sub.2 CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-F H H CH.sub.2 CH.sub.24-F 5-Cl H H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl H H CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl H H CH.sub.2 CH.sub.24-NO.sub.2 5-Cl H H CH.sub.2 CH.sub.24-SCF.sub.2 H 5-Cl H H CH.sub.2 CH.sub.24-CN 5-Cl H H CH.sub.2 CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl H H CH.sub.2 CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl H H CH.sub.2 CH.sub.24-Cl 5-Br H H CH.sub.2 CH.sub.24-Br 5-Br H H CH.sub.2 CH.sub.24-CF.sub.3 5-Br H H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Br H H CH.sub.2 CH.sub.24-OCF.sub.3 5-Br H H CH.sub.2 CH.sub.24-Cl 5-CN H H CH.sub.2 CH.sub.24-Br 5-CN H H CH.sub.2 CH.sub.24-CF.sub.3 5-CN H H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-CN H H CH.sub.2 CH.sub.24-OCF.sub.3 5-CN H H CH.sub.2 CH.sub.24-Cl 5-OMe H H CH.sub.2 CH.sub.24-Br 5-OMe H H CH.sub.2 CH.sub.24-CF.sub.3 5-OMe H H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H H H CH.sub.2 CH.sub.24-OCF.sub.3 5-OCF.sub.2 H H H CH.sub.2 CH.sub.24-CF.sub.3 5-OCF.sub.2 H H H CH.sub.2 CH.sub.24-Cl 5-OCF.sub.2 H H H CH.sub.2 CH.sub.24-Br 5-OCF.sub.2 H H H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-OCF.sub.3 H H CH.sub.2 CH.sub.24-OCF.sub.3 5-OCF.sub.3 H H CH.sub.2 CH.sub.24-CF.sub.3 5-OCF.sub.3 H H CH.sub.2 CH.sub.24-Cl 5-OCF.sub.3 H H CH.sub.2 CH.sub.24-Br 5-OCF.sub.3 H H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-OPh H H CH.sub.2 CH.sub.24-OCF.sub.3 5-OPh H H CH.sub.2 CH.sub.24-CF.sub.3 5-OPh H H CH.sub.2 CH.sub.24-Cl 5-OPh H H CH.sub.2 CH.sub.24-Br 5-OPh H H CH.sub.2 CH.sub.24-CF.sub.3 5-SMe H H CH.sub.2 CH.sub.24-Cl 5-SMe H H CH.sub.2 CH.sub.24-Br 5-SMe H H CH.sub.2 CH.sub.24-CF.sub.3 6-F H H CH.sub.2 CH.sub.24-Cl 6-F H H CH.sub.2 CH.sub.24-Br 6-F H H CH.sub.2 CH.sub.24-CF.sub.3 6-Cl H H CH.sub.2 CH.sub.24-Cl 6-Cl H H CH.sub.2 CH.sub.24-Br 6-Cl H H CH.sub.2 CH.sub.24-Cl 5-F H 4-F CH.sub.2 CH.sub.24-Br 5-F H 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-F H 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-F H 4-F CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F H 4-F CH.sub.2 CH.sub.24-OCF.sub.3 5-F H 4-F CH.sub.2 CH.sub.23,4-di-Cl 5-F H 4-F CH.sub.2 CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-F H 4-F CH.sub.2 CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-F H 4-F CH.sub.2 CH.sub.24-Cl 5-F H 4-Cl CH.sub.2 CH.sub.24-Br 5-F H 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 5-F H 4-Cl CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F H 4-Cl CH.sub.2 CH.sub.24-OCF.sub.3 5-F H 4-Cl CH.sub.2 CH.sub.24-Cl 5-F H 4-NO.sub.2 CH.sub.2 CH.sub.24-Br 5-F H 4-NO.sub.2 CH.sub.2 CH.sub.24-CF.sub.3 5-F H 4-NO.sub.2 CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F H 4-NO.sub.2 CH.sub.2 CH.sub.24-OCF.sub.3 5-F H 4-NO.sub.2 CH.sub.2 CH.sub.24-Cl 5-F H 4-CN CH.sub.2 CH.sub.24-Br 5-F H 4-CN CH.sub.2 CH.sub.24-CF.sub.3 5-F H 4-CN CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F H 4-CN CH.sub.2 CH.sub. 24-OCF.sub.3 5-F H 4-CN CH.sub.2 CH.sub.24-Cl 5-F H 4-CF.sub.3 CH.sub.2 CH.sub.24-Br 5-F H 4-CF.sub.3 CH.sub.2 CH.sub.24-CF.sub.3 5-F H 4-CF.sub.3 CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F H 4-CF.sub.3 CH.sub.2 CH.sub.24-CF.sub.3 5-F H 4-OCF.sub.2 H CH.sub.2 CH.sub.24-Cl 5-F H 4-OCF.sub.2 H CH.sub.2 CH.sub.24-Br 5-F H 4-OCF.sub.2 H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F H 4-OCF.sub.2 H CH.sub.2 CH.sub.24-OCF.sub.3 5-F H 4-OCF.sub.2 H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl H 4-F CH.sub.2 CH.sub.24-Cl 5-Cl H 4-F CH.sub.2 CH.sub.24-Br 5-Cl H 4-F CH.sub.2 CH.sub.24-F 5-Cl H 4-F CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl H 4-F CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl H 4-F CH.sub.2 CH.sub.24-NO.sub.2 5-Cl H 4-F CH.sub.2 CH.sub.23,4-di-Cl 5-Cl H 4-F CH.sub.2 CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl H 4-F CH.sub.2 CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl H 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-Cl H 4-Cl CH.sub.2 CH.sub.24-Cl 5-Cl H 4-Cl CH.sub.2 CH.sub.24-Br 5-Cl H 4-Cl CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl H 4-Cl CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl H 4-Cl CH.sub.2 CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl H 4-Cl CH.sub.2 CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl H 4-Cl CH.sub.2 CH.sub.24-CN 5-Cl H 4-Cl CH.sub.2 CH.sub.24-F 5-Cl H 4-Cl CH.sub.2 CH.sub.24-NO.sub.2 5-Cl H 4-Cl CH.sub.2 CH.sub.24H 5-Cl H 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 5-CF.sub.3 H 4-F CH.sub.2 CH.sub.24-OCF.sub.3 5-CF.sub.3 H 4-F CH.sub.2 CH.sub.24-Cl 5-CF.sub.3 H 4-F CH.sub.2 CH.sub.24-Br 5-CF.sub.3 H 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-OCF.sub.2 H H 4-F CH.sub.2 CH.sub.24-Cl 5-OCF.sub.2 H H 4-F CH.sub.2 CH.sub.24-Br 5-OCF.sub.2 H H 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-OCF.sub.2 H H 4-Cl CH.sub.2 C.q24-Cl 5-OCF.sub.2 H H 4-Cl CH.sub.2 CH.sub.24-Br 5-OCF.sub.2 H H 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 4-F H 4-F CH.sub.2 CH.sub.24-Cl 4-F H 4-F CH.sub.2 CH.sub.24-Br 4-F H 4-F CH.sub.2 CH.sub.24-CF.sub.3 4-F H 4-Cl CH.sub.2 CH.sub.24-Cl 4-F H 4-Cl CH.sub.2 CH.sub.24-Br 4-F H 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 4-Cl H 4-Cl CH.sub.2 CH.sub.24-Cl 4-Cl H 4-Cl CH.sub.2 CH.sub.24-Br 4-Cl H 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 4-Cl H 4-F CH.sub.2 CH.sub.24-Cl 4-Cl H 4-F CH.sub.2 CH.sub.24-Br 4-Cl H 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-Cl H 4-CF.sub.3 CH.sub.2 CH.sub.24-Cl 5-Cl H 4-CF.sub.3 CH.sub.2 CH.sub.24-Br 5-Cl H 4-CF.sub.3- CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl H 4-CF.sub.3 CH.sub.2 CH.sub.24-CF.sub.3 5-Cl H 4-Me CH.sub.2 CH.sub.24-Cl 5-Cl H 4-Me CH.sub.2 CH.sub.24-Br 5-Cl H 4-Me CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl H 4-Me CH.sub.2 CH.sub.24-CF.sub.3 5-Cl H 4-SMe CH.sub.2 CH.sub.24-Cl 5-Cl H 4-SMe CH.sub.2 CH.sub.24-Br 5-Cl H 4-SMe CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl H 4-SMe CH.sub.2 CH.sub.24-CF.sub.3 5-Cl H 4-NO2 CH.sub.2 CH.sub.24-Cl 5-Cl H 4-NO2 CH.sub.2 CH.sub.24-Br 5-Cl H 4-NO2 CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl H 4-NO2 CH.sub.2 CH.sub.24-CF.sub.3 5-Cl H 4-OPh CH.sub.2 CH.sub.24-Cl 5-Cl H 4-OPh CH.sub.2 CH.sub.24-Br 5-Cl H 4-OPh CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl H 4-OPh CH.sub.2 CH.sub.24-CF.sub.3 H Me H CH.sub.2 CH.sub.24-Cl H Me H CH.sub.2 CH.sub.24-Br H Me H CH.sub.2 CH.sub.24-OCF.sub.2 H H Me H CH.sub.2 CH.sub.24-OCF.sub.3 H Me H CH.sub.2 CH.sub.24-CF.sub.3 4-F Me H CH.sub.2 CH.sub.24-Cl 4-F Me H CH.sub.2 CH.sub.24-Br 4-F Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 4-F Me H CH.sub.2 CH.sub.24-OCF.sub.3 4-F Me H CH.sub.2 CH.sub.24-CF.sub.3 4-Cl Me H CH.sub.2 CH.sub.24-Cl 4-Cl Me H CH.sub.2 CH.sub.24-Br 4-Cl Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 4-Cl Me H CH.sub.2 CH.sub.24-OCF.sub.3 4-Cl Me H CH.sub.2 CH.sub.24-CF.sub.3 5-F Me H CH.sub.2 CH.sub.24-Cl 5-F Me H CH.sub.2 CH.sub.24-Br 5-F Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F Me H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Me H CH.sub.2 CH.sub.24-Cl 5-Cl Me H CH.sub.2 CH.sub.24-Br 5-Cl Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl Me H CH.sub.2 CH.sub.24-CF.sub.3 4-F Me 4-F CH.sub.2 CH.sub.24-Cl 4-F Me 4-F CH.sub.2 CH.sub.24-Br 4-F Me 4-F CH.sub.2 CH.sub.24-OCF.sub.2 H 4-F Me 4-F CH.sub.2 CH.sub.24-CF.sub.3 4-Cl Me 4-F CH.sub.2 CH.sub.24-Cl 4-Cl Me 4-F CH.sub.2 CH.sub.24-Br 4-Cl Me 4-F CH.sub.2 CH.sub.24-OCF.sub.2 H 4-Cl Me 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-F Me 4-F CH.sub.2 CH.sub.24-Cl 5-F Me 4-F CH.sub.2 CH.sub.24-Br 5-F Me 4-F CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F Me 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Me 4-F CH.sub.2 CH.sub.24-Cl 5-Cl Me 4-F CH.sub.2 CH.sub.24-Br 5-Cl Me 4-F CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl Me 4-F CH.sub.2 CH.sub.24-CF.sub.3 4-F Me 4-Cl CH.sub.2 CH.sub.24-Cl 4-F Me 4-Cl CH.sub.2 CH.sub.24-Br 4-F Me 4-Cl CH.sub.2 CH.sub.24-OCF.sub.2 H 4-F Me 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 4-Cl Me 4-Cl CH.sub.2 CH.sub.24-Cl 4-Cl Me 4-Cl CH.sub.2 CH.sub.24-Br 4-Cl Me 4-Cl CH.sub.2 CH.sub.24-OCF.sub.2 H 4-Cl Me 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 5-F Me 4-Cl CH.sub.2 CH.sub.24-Cl 5-F Me 4-Cl CH.sub.2 CH.sub.24-Br 5-F Me 4-Cl CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F Me 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Me 4-Cl CH.sub.2 CH.sub.24-Cl 5-Cl Me 4-Cl CH.sub.2 CH.sub.24-Br 5-Cl Me 4-Cl CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Me 4-Cl CH.sub.2 CH.sub.24-Cl 5-Cl Me 4-Cl CH.sub.2 CH.sub.24-Br 5-Cl Me 4-Cl CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Et 4-F CH.sub.2 CH.sub.24-Cl 5-Cl Et 4-F CH.sub.2 CH.sub.24-Br 5-Cl Et 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Et 4-Cl CH.sub.2 CH.sub.24-Cl 5-Cl Et 4-Cl CH.sub.2 CH.sub.24-Br 5-Cl Et 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 5-Cl allyl 4-F CH.sub.2 CH.sub.24-Cl 5-Cl allyl 4-F CH.sub.2 CH.sub.24-Br 5-Cl allyl 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-Cl allyl 4-Cl CH.sub.2 CH.sub.24-Cl 5-Cl allyl 4-Cl CH.sub.2 CH.sub.24-Br 5-Cl allyl 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 5-Cl propargyl 4-F CH.sub.2 CH.sub.24-Cl 5-Cl propargyl 4-F CH.sub.2 CH.sub.24-Br 5-Cl propargyl 4-F CH.sub.2 CH.sub.24-CF.sub.3 5-Cl propargyl 4-Cl CH.sub.2 CH.sub.24-Cl 5-Cl propargyl 4-Cl CH.sub.2 CH.sub.24-Br 5-Cl propargyl 4-Cl CH.sub.2 CH.sub.24-CF.sub.3 5-F H 4-F NMe4-OCF.sub.3 5-F H 4-F NMe4-CF.sub.3 5-Cl H 4-F NMe4-OCF.sub.3 5-Cl H 4-F NMe4-CF.sub.3 4-F Me 4-Cl NMe4-Cl 4-F Me 4-Cl NMe4-Br 4-F Me 4-Cl NMe4-OCF.sub.2 H 4-F Me 4-Cl NMe4-CF.sub.3 4-Cl Me 4-Cl NMe4-Cl 4-Cl Me 4-Cl NMe4-Br 4-Cl Me 4-Cl NMe4-OCF.sub.2 H 4-Cl Me 4-Cl NMe4-CF.sub.3 5-F Me 4-Cl NMe4-Cl 5-F Me 4-Cl NMe4-Br 5-F Me 4-Cl NMe4-OCF.sub.2 H 5-F Me 4-Cl NMe4-CF.sub.3 5-Cl Me 4-Cl NMe4-Cl 5-Cl Me 4-Cl NMe4-Br 5-Cl Me 4-Cl NMe4-OCF.sub.2 H 5-Cl Me 4-Cl NMe4-CF.sub.3 5-Cl Me 4-Cl NMe4-Cl 5-Cl Me 4-Cl NMe4-Br 5-Cl Me 4-Cl NMe4-OCF.sub.2 H 5-Cl Me 4-Cl NMe4-F 5-F H H CHMe4-Cl 5-F H H CHMe4-Br 5-F H H CHMe4-CF.sub.3 5-F H H CHMe4-OCF.sub.2 H 5-F H H CHMe4-OCF.sub.3 5-F H H CHMe4-NO.sub.2 5-F H H CHMe4-SCF.sub.2 H 5-F H H CHMe4-CN 5-F H H CHMe3,4-CF.sub.2 CF.sub.2 O 5-F H H CHMe3,4-CH.sub.2 C(Me).sub.2 O 5-F H H CHMe4-F 5-Cl H H CHMe4-Cl 5-Cl H H CHMe4-Br 5-Cl H H CHMe4-CF.sub.3 5-Cl H H CHMe4-OCF.sub.2 H 5-Cl H H CHMe4-OCF.sub.3 5-Cl H H CHMe4-NO.sub.2 5-Cl H H CHMe4-CF.sub.3 4-Cl H 4-Cl CHMe4-Cl 4-Cl H 4-Cl CHMe4-Br 4-Cl H 4-Cl CHMe4-CF.sub.3 4-Cl H 4-F CHMe4-Cl 4-Cl H 4-F CHMe4-Br 4-Cl H 4-F CHMe4-CF.sub.3 5-Cl H 4-CF.sub.3 CHMe4-Cl 5-Cl H 4-CF.sub.3 CHMe4-Br 5-Cl H 4-CF.sub.3 CHMe4-OCF.sub.2 H 5-Cl H 4-CF.sub.3 CHMe4-CF.sub.3 5-Cl H 4-Me CHMe4-Cl 5-Cl H 4-Me CHMe4-Br 5-Cl H 4-Me CHMe4-OCF.sub.2 H 5-Cl H 4-Me CHMe4-CF.sub.3 5-Cl H 4-SMe CHMe4-Cl 5-Cl H 4-SMe CHMe4-Br 5-Cl H 4-SMe CHMe4-OCF.sub.2 H 5-Cl H 4-SMe CHMe4-CF.sub.3 4-F Me 4-Cl CHMe4-Cl 4-F Me 4-Cl CHMe4-Br 4-F Me 4-Cl CHMe4-OCF.sub.2 H 4-F Me 4-Cl CHMe4-CF.sub.3 4-Cl Me 4-Cl CHMe4-Cl 4-Cl Me 4-Cl CHMe4-Br 4-Cl Me 4-Cl CHMe4-OCF.sub.2 H 4-Cl Me 4-Cl CHMe4-CF.sub.3 5-F Me 4-Cl CHMe4-Cl 5-F Me 4-Cl CHMe4-Br 5-F Me 4-Cl CHMe4-OCF.sub.2 H 5-F Me 4-Cl CHMe4-CF.sub.3 5-Cl Me 4-Cl CHMe4-Cl 5-Cl Me 4-Cl CHMe4-Br 5-Cl Me 4-Cl CHMe4-OCF.sub.2 H 5-Cl Me 4-Cl CHMe4-CF.sub.3 5-Cl Me 4-Cl CHMe4-Cl 5-Cl Me 4-Cl CHMe4-Br 5-Cl Me 4-Cl CHMe4-OCF.sub.2 H 5-Cl Me 4-Cl CHMe4-CF.sub.3 4-F Me 4-Cl SO.sub.24-Cl 4-F Me 4-Cl SO.sub.24-Br 4-F Me 4-Cl SO.sub.24-OCF.sub.2 H 4-F Me 4-Cl SO.sub.24-CF.sub.3 4-Cl Me 4-Cl SO.sub.24-Cl 4-Cl Me 4-Cl SO.sub.24-Br 4-Cl Me 4-Cl SO.sub.24-OCF.sub.2 H 4-Cl Me 4-Cl SO.sub.24-CF.sub.3 5-F Me 4-Cl SO.sub.24-Cl 5-F Me 4-Cl SO.sub.24-Br 5-F Me 4-Cl SO.sub.24-OCF.sub.2 H 5-F Me 4-Cl SO.sub.24-CF.sub.3 5-Cl Me 4-Cl SO.sub.24-Cl 5-Cl Me 4-Cl SO.sub.24-Br 5-Cl Me 4-Cl SO.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl SO.sub.24-CF.sub.3 5-Cl Me 4-Cl SO.sub.24-Cl 5-Cl Me 4-Cl SO.sub.24-Br 5-Cl Me 4-Cl SO.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl SO.sub.24-F 5-F H H C(Me).sub.24-Cl 5-F H H C(Me).sub.24-Br 5-F H H C(Me).sub.24-CF.sub.3 5-F H H C(Me).sub.24-OCF.sub.2 H 5-F H H C(Me).sub.24-OCF.sub.3 5-F H H C(Me).sub.24-NO.sub.2 5-F H H C(Me).sub.24-SCF.sub.2 H 5-F H H C(Me).sub.24-CN 5-F H H C(Me).sub.23,4-CF.sub.2 CF.sub.2 O 5-F H H C(Me).sub.23,4-CH.sub.2 C(Me).sub.2 O 5-F H H C(Me).sub.24-F 5-Cl H H C(Me).sub.24-Cl 5-Cl H H C(Me).sub.24-Br 5-Cl H H C(Me).sub.24-CF.sub.3 5-Cl H H C(Me).sub.24-OCF.sub.2 H 5-Cl H H C(Me).sub.24-OCF.sub.3 5-Cl H H C(Me).sub.24-NO.sub.2 5-Cl H H C(Me).sub.24-CF.sub.3 4-Cl H 4-Cl C(Me).sub.24-Cl 4-Cl H 4-Cl C(Me).sub.24-Br 4-Cl H 4-Cl C(Me).sub.24-CF.sub.3 4-Cl H 4-F C(Me).sub.24-Cl 4-Cl H 4-F C(Me).sub.24-Br 4-Cl H 4-F C(Me).sub.24-OCF.sub.3 4-Cl H 4-F C(Me).sub.24-CF.sub.3 5-Cl H 4-CF.sub.3 C(Me).sub.24-Cl 5-Cl H 4-CF.sub.3 C(Me).sub.24-Br 5-Cl H 4-CF.sub.3 C(Me).sub.24-OCF.sub.2 H 5-Cl H 4-CF.sub.3 C(Me).sub.24-OCF.sub.3 5-Cl H 4-CF.sub.3 C(Me).sub.24-CF.sub.3 5-Cl H 4-Me C(Me).sub.24-Cl 5-Cl H 4-Me C(Me).sub.24-Br 5-Cl H 4-Me C(Me).sub.24-OCF.sub.2 H 5-Cl H 4-Me C(Me).sub.24-CF.sub.3 5-F Me 4-F C(Me).sub.24-Cl 5-F Me 4-F C(Me).sub.24-Br 5-F Me 4-F C(Me).sub.24-OCF.sub.3 5-F Me 4-F C(Me).sub.24-OCF.sub.2 H 5-F Me 4-F C(Me).sub.24-CF.sub.3 5-Cl H 4-SMe C(Me).sub.24-Cl 5-Cl H 4-SMe C(Me).sub.24-Br 5-Cl H 4-SMe C(Me).sub.24-OCF.sub.2 H 5-Cl H 4-SMe C(Me).sub.24-CF.sub.3 4-F Me 4-Cl C(Me).sub.24-Cl 4-F Me 4-Cl C(Me)z4-Br 4-F Me 4-Cl C(Me).sub.24-OCF.sub.2 H 4-F Me 4-Cl C(Me).sub.24-CF.sub.3 4-Cl Me 4-Cl C(Me).sub.24-Cl 4-Cl Me 4-Cl C(Me).sub.24-Br 4-Cl Me 4-Cl C(Me).sub.24-OCF.sub.2 H 4-Cl Me 4-Cl C(Me).sub.24-CF.sub.3 5-F Me 4-Cl C(Me).sub.24-Cl 5-F Me 4-Cl C(Me).sub.24-Br 5-F Me 4-Cl C(Me).sub.24-OCF.sub.2 H 5-F Me 4-Cl C(Me).sub.24-CF.sub.3 5-Cl Me 4-Cl C(Me).sub.24-Cl 5-Cl Me 4-Cl C(Me).sub.24-Br 5-Cl Me 4-Cl C(Me).sub.24-OCF.sub.2 H 5-Cl Me 4-Cl C(Me).sub.24-CF.sub.3 5-Cl Me 4-Cl C(Me).sub.24-Cl 5-Cl Me 4-Cl C(Me).sub.24-Br 5-Cl Me 4-Cl C(Me).sub.24-OCF.sub.2 H 5-Cl Me 4-Cl C(Me).sub.24-CF.sub.3 5-F Me 4-F C(Me).sub.24-OCF.sub.3 5-F Me 4-F C(Me).sub.24-CF.sub.3 4-Cl Me 4-Cl S(O)4-Cl 4-Cl Me 4-Cl S(O)4-Br 4-Cl Me 4-Cl S(O)4-OCF.sub.2 H 4-Cl Me 4-Cl S(O)4-CF.sub.3 5-F Me 4-Cl S(O)4-Cl 5-F Me 4-Cl S(O)4-Br 5-F Me 4-Cl S(O)4-OCF.sub.2 H 5-F Me 4-Cl S(O)4-CF.sub.3 5-Cl Me 4-Cl S(O)4-Cl 5-Cl Me 4-Cl S(O)4-Br 5-Cl Me 4-Cl S(O)4-OCF.sub.2 H 5-Cl Me 4-Cl S(O)4-CF.sub.3 5-Cl Me 4-Cl S(O)4-Cl 5-Cl Me 4-Cl S(O)4-Br 5-Cl Me 4-Cl S(O)4-OCF.sub.2 H 5-Cl Me 4-Cl S(O)4-F 5-F H H OCH.sub.24-Cl 5-F H H OCH.sub.24-Br 5-F H H OCH.sub.24-CF.sub.3 5-F H H OCH.sub.24-OCF.sub.2 H 5-F H H OCH.sub.24-OCF.sub.3 5-F H H OCH.sub.24-CF.sub.3 4-Cl H 4-Cl OCH.sub.24-Cl 4-Cl H 4-Cl OCH.sub.24-Br 4-Cl H 4-Cl OCH.sub.24-CF.sub.3 4-Cl H 4-F OCH.sub.24-Cl 4-Cl H 4-F OCH.sub.24-Br 4-Cl H 4-F OCH.sub.24-CF.sub.3 5-Cl H 4-CF.sub.3 OCH.sub.24-Cl 5-Cl H 4-CF.sub.3 OCH.sub.24-Br 5-Cl H 4-CF.sub.3 OCH.sub.24-OCF.sub.2 H 5-Cl H 4-CF.sub.3 OCH.sub.24-CF.sub.3 4-F Me 4-Cl OCH.sub. 24-Cl 4-F Me 4-Cl OCH.sub.24-Br 4-F Me 4-Cl OCH.sub.24-OCF.sub.2 H 4-F Me 4-Cl OCH.sub.24-CF.sub.3 4-Cl Me 4-Cl OCH.sub.24-Cl 4-Cl Me 4-Cl OCH.sub.24-Br 4-Cl Me 4-Cl OCH.sub.24-OCF.sub.2 H 4-Cl Me 4-Cl OCH.sub.24-CF.sub.3 5-F Me 4-Cl OCH.sub.24-Cl 5-F Me 4-Cl OCH.sub.24-Br 5-F Me 4-Cl OCH.sub.24-OCF.sub.2 H 5-F Me 4-Cl OCH.sub.24-CF.sub.3 5-Cl Me 4-Cl OCH.sub.24-Cl 5-Cl Me 4-Cl OCH.sub.24-Br 5-Cl Me 4-Cl OCH.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl OCH.sub.24-CF.sub.3 5-Cl Me 4-Cl OCH.sub.24-Cl 5-Cl Me 4-Cl OCH.sub.24-Br 5-Cl He 4-Cl OCH.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl OCH.sub.24-F 5-F H H CH.sub.2 O4-Cl 5-F H H CH.sub.2 O4-Br 5-F H H CH.sub.2 O4-CF.sub.3 5-F H H CH.sub.2 O4-OCF.sub.2 H 5-F H H CH.sub.2 O4-OCF.sub.3 5-F H H CH.sub.2 O4-NO.sub.2 5-F H H CH.sub.2 O4-SCF.sub.2 H 5-F H H CH.sub.2 O4-CN 5-F H H CH.sub.2 O3,4-CF.sub. 2 CF.sub.2 O 5-F H H CH.sub.2 O3,4-CH.sub.2 C(Me).sub.2 O 5-F H H CH.sub.2 O4-CF.sub.3 4-Cl H 4-Cl CH.sub.2 O4-Cl 4-Cl H 4-Cl CH.sub.2 O4-Br 4-Cl H 4-Cl CH.sub.2 O4-CF.sub.3 4-Cl H 4-F CH.sub.2 O4-Cl 4-Cl H 4-F CH.sub.2 O4-Br 4-Cl H 4-F CH.sub.2 O4-CF.sub.3 5-Cl H 4-CF.sub.3 CH.sub.2 O4-Cl 5-Cl H 4-CF.sub.3 CH.sub.2 O4-Br 5-Cl H 4-CF.sub.3 CH.sub.2 O4-OCF.sub.2 H 5-Cl H 4-CF.sub.3 CH.sub.2 O4-CF.sub.3 4-F Me 4-Cl CH.sub.2 O4-Cl 4-F Me 4-Cl CH.sub.2 O4-Br 4-F Me 4-Cl CH.sub.2 O4-OCF.sub.2 H 4-F Me 4-Cl CH.sub.2 O4-CF.sub.3 4-Cl Me 4-Cl CH.sub.2 O4-Cl 4-Cl Me 4-Cl CH.sub.2 O4-Br 4-Cl Me 4-Cl CH.sub.2 O4-OCF.sub.2 H 4-Cl Me 4-Cl CH.sub.2 O4-CF.sub.3 5-F Me 4-Cl CH.sub.2 O4-Cl 5-F Me 4-Cl CH.sub.2 O4-Br 5-F Me 4-Cl CH.sub.2 O4-OCF.sub.2 H 5-F Me 4-Cl CH.sub.2 O4-CF.sub.3 5-Cl Me 4-Cl CH.sub.2 O4-Cl 5-Cl Me 4-Cl CH.sub.2 O4-Br 5-Cl Me 4-Cl CH.sub.2 O4-OCF.sub.2 H 5-Cl Me 4-Cl CH.sub.2 O4-CF.sub.3 5-Cl Me 4-Cl CH.sub.2 O4-Cl 5-Cl Me 4-Cl CH.sub.2 O4-Br 5-Cl Me 4-Cl CH.sub.2 O4-OCF.sub.2 H 5-Cl Me 4-Cl CH.sub.2 O4-F 5-F H H SCH.sub.24-Cl 5-F H H SCH.sub.24-Br 5-F H H SCH.sub.24-CF.sub.3 5-F H H SCH.sub.24-OCF.sub.2 H 5-F H H SCH.sub.24-OCF.sub.3 5-F H H SCH.sub.24-Cl 5-Cl H H SCH.sub.24-Br 5-Cl H H SCH.sub.24-CF.sub.3 5-Cl H H SCH.sub.24-OCF.sub.2 H 5-Cl H H SCH.sub.24-OCF.sub.3 5-Cl H H SCH.sub.24-CF.sub.3 4-Cl H 4-Cl SCH.sub.24-Cl 4-Cl H 4-Cl SCH.sub.24-Br 4-Cl H 4-Cl SCH.sub.24-CF.sub.3 4-Cl H 4-F SCH.sub.24-Cl 4-Cl H 4-F SCH.sub.24-Br 4-Cl H 4-F SCH.sub.24-CF.sub.3 5-Cl H 4-CF.sub.3 SCH.sub.24-Cl 5-Cl H 4-CF.sub.3 SCH.sub.24-Br 5-Cl H 4-CF.sub.3 SCH.sub.24-OCF.sub.2 H 5-Cl H 4-CF.sub.3 SCH.sub.24-CF.sub.3 4-F Me 4-Cl SCH.sub.24-Cl 4-F Me 4-Cl SCH.sub.24-Br 4-F Me 4-Cl SCH.sub.24-OCH.sub.2 H 4-F Me 4-Cl SCH.sub.24-CF.sub.3 4-Cl Me 4-Cl SCH.sub.24-Cl 4-Cl Me 4-Cl SCH.sub.24-Br 4-Cl Me 4-Cl SCH.sub.24-OCF.sub.2 H 4-Cl Me 4-Cl SCH.sub.24-CF.sub.3 5-F Me 4-F SCH.sub.24-Cl 5-F Me 4-F SCH.sub.24-Br 5-F Me 4-F SCH.sub.24-OCF.sub.2 H 5-F Me 4-F SCH.sub.24-CF.sub.3 5-Cl Me 4-Cl SCH.sub.24-Cl 5-Cl Me 4-Cl SCH.sub.24-Br 5-Cl Me 4-Cl SCH.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl SCH.sub.24-CF.sub.3 5-Cl Me 4-Cl SCH.sub.24-Cl 5-Cl Me 4-Cl SCH.sub.24-Br 5-Cl Me 4-Cl SCH.sub.24-OCF.sub.2 H 5-Cl Me 4-Cl SCH.sub.24-F 5-F H H CH.sub.2 S4-Cl 5-F H H CH.sub.2 S4-Br 5-F H H CH.sub.2 S4-CF.sub.3 5-F H H CH.sub.2 S4-OCF.sub.2 H 5-F H H CH.sub.2 S4-OCF.sub.3 5-F H H CH.sub.2 S4-CF.sub.3 4-F H 4-Cl CH.sub.2 S4-Cl 4-F H 4-Cl CH.sub.2 S4-Br 4-F H 4-Cl CH.sub.2 S4-CF.sub.3 5-F H 4-F CH.sub.2 S4-Cl 5-F H 4-F CH.sub.2 S4-Br 5-F H 4-F CH.sub.2 S______________________________________
TABLE 12______________________________________ ##STR20##R.sub.1 R.sub.2 R.sub.3 R.sub.4 A______________________________________4-CF.sub.3 H H H CH.sub.24-Cl H H H CH.sub.24-Br H H H CH.sub.24-OCF.sub.2 H H H H CH.sub.24-OCF.sub.3 H H H CH.sub.24-CF.sub.3 4-F H H CH.sub.24-Cl 4-F H H CH.sub.24-Br 4-F H H CH.sub.24-OCF.sub.2 H 4-F H H CH.sub.24-OCF.sub.3 4-F H H CH.sub.24-CF.sub.3 4-Cl H H CH.sub.24-Cl 4-Cl H H CH.sub.24-Br 4-Cl H H CH.sub.24-OCF.sub.2 H 4-Cl H H CH.sub.24-OCF.sub.3 4-Cl H H CH.sub.24-OCF.sub.2 H 5-F H H CH.sub.24-OCF.sub.3 5-F H H CH.sub.24-CF.sub.3 4-F Me R CH.sub.24-Cl 4-F Me H CH.sub.24-Br 4-F Me H CH.sub.24-OCF.sub.3 4-F Me H CH.sub.24-OCF.sub.2 H 4-F Me H CH.sub.24-OCF.sub.3 5-Cl Me H CH.sub.24-OCF.sub.2 H 5-Cl Me H CH.sub.24-CF.sub.3 5-CF.sub.3 Me H CH.sub.24-OCF.sub.3 5-CF.sub.3 Me H CH.sub.24-Cl 5-CF.sub.3 Me H CH.sub.24-Br 5-CF.sub.3 Me H CH.sub.24-OCF.sub.2 H 5-CF.sub.3 Me H CH.sub.24-CF.sub.3 5-OCF.sub.2 H Me H CH.sub.24-Cl 5-OCF.sub.2 H Me H CH.sub.24-Br 5-OCF.sub.2 H Me H CH.sub.24-OCF.sub.3 5-OCF.sub.2 H Me H CH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H Me H CH.sub.24-OCH.sub.3 5-F Me H CH.sub.24-CF.sub.3 5-Cl Et R CH.sub.24-Cl 5-Cl Et H CH.sub.24-Br 5-Cl Et H CH.sub.24-OCF.sub.3 5-Cl Et H CH.sub.24-CF.sub.3 5-OCF.sub.2 H Et H CH.sub.24-Cl 5-OCF.sub.2 H Et H CH.sub.24-Br 5-OCF.sub.2 H Et H CH.sub.24-OCF.sub.3 5-OCF.sub.2 H Et H CH.sub.24-CF.sub.3 5-F n-Bu H CH.sub.24-Cl 5-F n-Bu H CH.sub.24-Br 5-F n-Bu H CH.sub.24-OCF.sub.3 5-F n-Bu H CH.sub.24-CF.sub.3 4-F n-Bu H CH.sub.24-Cl 4-F n-Bu H CH.sub.24-Br 4-F n-Bu H CH.sub.24-OCF.sub.3 4-F n-Bu H CH.sub.24-CF.sub.3 5-Cl allyl H CH.sub.24-Cl 5-Cl allyl H CH.sub.24-Br 5-Cl allyl H CH.sub.24-OCF.sub.3 5-F i-Pr H CH.sub.24-CF.sub.3 4-F i-Pr H CH.sub.24-OCF.sub.3 4-F i-Pr H CH.sub.24-CF.sub.3 4-CF.sub.3 i-Pr H CH.sub.24-OCF.sub.3 4-CF.sub.3 i-Pr H CH.sub.24-CF.sub.3 5-OCF.sub.2 H i-Pr H CH.sub.24-OCF.sub.3 5-OCF.sub.2 H i-Pr H CH.sub.24-CF.sub.3 5-CF.sub.3 i-Pr H CH.sub.24-OCF.sub.3 5-CF.sub.3 i-Pr H CH.sub.24-CF.sub.3 5-Cl Me Me CH.sub.24-Cl 5-Cl Me Me CH.sub.24-Br 5-Cl Me Me CH.sub.24-CF.sub.3 5-F Me Me CH.sub.24-Cl 5-F Me Me CH.sub.24-Br 5-F Me Me CH.sub.24-CF.sub.3 5-OCF.sub.2 H Me Me CH.sub.24-Cl 5-OCF.sub.2 H Me Me CH.sub.24-Br 5-OCF.sub.2 H Me Me CH.sub.24-CF.sub.3 5-OCF.sub.3 Me Me CH.sub.24-Cl 5-OCF.sub.3 Me Me CH.sub.24-Br 5-OCF.sub.3 Me Me CH.sub.24-CF.sub.3 4-F Me Me CH.sub.24-Cl 4-F Me Me CH.sub.24-Br 4-F Me Me CH.sub.24-CF.sub.3 5-Br Me Me CH.sub.24-Cl 5-Br Me Me CH.sub.24-Br 5-Br Me Me CH.sub.24-CF.sub.3 5-Cl CH.sub.2 Ph H CH.sub.24-Cl 5-Cl CH.sub.2 Ph H CH.sub.24-Br 5-Cl CH.sub.2 Ph H CH.sub.24-OCF.sub.3 5-Cl CH.sub.2 Ph H CH.sub.24-OCF.sub.2 H 5-Cl CH.sub.2 Ph H CH.sub.24-CF.sub.3 5-F CH.sub.2 Ph-4-F H CH.sub.24-Cl 5-F CH.sub.2 Ph-4-F H CH.sub.24-Br 5-F CH.sub.2 Ph-4-F H CH.sub.24-OCF.sub.2 H 5-F CH.sub.2 Ph-4-F H CH.sub.24-OCF.sub.3 5-F CH.sub.2 Ph-4-F H CH.sub.24-CF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.24-Cl 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.24-Br 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.24-OCF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.24-CF.sub.3 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.24-Cl 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.24-Br 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.24-OCF.sub.3 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.24-OCF.sub.2 H 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me H CH.sub.24-Cl 5-Cl CO.sub.2 Me H CH.sub.24-Br 5-Cl CO.sub.2 Me H CH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me H CH.sub.24-OCF.sub.3 5-Cl CO.sub.2 Me H CH.sub.24-CF.sub.3 5-F CO.sub.2 Me H CH.sub.24-Cl 5-F CO.sub.2 Me H CH.sub.24-Br 5-F CO.sub.2 Me H CH.sub.24-OCF.sub.2 H 5-F CO.sub.2 Me H CH.sub.24-OCF.sub.3 5-F CO.sub.2 Me H CH.sub.24-CF.sub.3 4-F CO.sub.2 Me H CH.sub.24-Cl 4-F CO2 Me H CH.sub.24-Br 4-F CO.sub.2 Me H CH.sub.24-CF.sub.3 4-Cl CO.sub.2 Me H CH.sub.24-Cl 4-Cl CO.sub.2 Me H CH.sub.24-Br 4-Cl CO.sub.2 Me H CH.sub.24-CF.sub. 3 5-CF.sub.3 CO.sub.2 Me H CH.sub.24-OCF.sub.3 5-CF.sub.3 CO.sub.2 Me H CH.sub.24-CF.sub.3 5-OCF.sub.3 CO.sub.2 Me H CH.sub.24-OCF.sub.3 5-OCF.sub.3 CO.sub.2 Me H CH.sub.24-CF.sub.3 H CO.sub.2 Me Me CH.sub.24-Cl H CO.sub.2 Me Me CH.sub.24-Br H CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H H CO.sub.2 Me Me CH.sub.24-OCF.sub.3 H CO.sub.2 Me Me CH.sub.23,4-CF.sub.2 CF.sub.2 O H CO.sub.2 Me Me CH.sub.23,4-CH.sub.2 C(Me).sub.2 O H CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me Me CH.sub.24-Cl 5-Cl CO.sub.2 Me Me CH.sub.24-Br 5-Cl CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me Me CH.sub.24-OCF.sub.3 5-Cl CO.sub.2 Me Me CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl CO.sub.2 Me Me CH.sub.23,4-CF.sub.2 C(Me).sub.2 O 5-Cl CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-F CO.sub.2 Me Me CH.sub.24-Cl 5-F CO.sub.2 Me Me CH.sub.24-Br 5-F CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 5-F CO.sub.2 Me Me CH.sub.24-OCF.sub.3 5-F CO.sub.2 Me Me CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-F CO.sub.2 Me Me CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-F CO.sub.2 Me Me CH.sub.24-CF.sub.3 4-F CO.sub.2 Me Me CH.sub.24-Cl 4-F CO.sub.2 Me Me CH.sub.24-Br 4-F CO.sub.2 Me Me CH.sub.24-OCF.sub.3 4-F CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 4-F CO.sub.2 Me Me CH.sub.23,4-CF.sub.2 CF.sub.2 O 4-F CO.sub.2 Me Me CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 4-F CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-Me CO.sub.2 Me Me CH.sub.24-Cl 5-Me CO.sub.2 Me Me CH.sub.24-Br 5-Me CO.sub.2 Me Me CH.sub.24-OCF.sub.3 5-Me CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 5-Me CO.sub.2 Me Me CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Me CO.sub.2 Me He CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Me CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-Br CO.sub.2 Me Me CH.sub.24-Cl 5-Br CO.sub.2 Me Me CH.sub.24-Br 5-Br CO.sub.2 Me Me CH.sub.24-OCF.sub.3 5-Br CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 5-Br CO.sub.2 Me Me CH.sub.23,4-CH.sub.2 CF.sub.2 O 5-Br CO.sub.2 Me Me CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Br CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me CH.sub.24-Cl 5-OCF.sub.2 H CO.sub.2 Me Me CH.sub.24-Br 5-OCF.sub.2 H CO.sub.2 Me Me CH.sub.24-OCF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H CO.sub.2 Me Me CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-OCF.sub.2 H CO.sub.2 Me Me CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-OCF.sub.2 H CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-OCF.sub.3 CO.sub.2 Me Me CH.sub.24-Cl 5-OCF.sub.3 CO.sub.2 Me Me CH.sub.24-Br 5-OCF.sub.3 CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 5-OCF.sub.3 CO.sub.2 Me Me CH.sub.24-OCF.sub.3 5-OCF.sub.3 CO.sub.2 Me Me CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-OCF.sub.3 CO.sub.2 Me Me CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-OCF.sub.3 CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-CN CO.sub.2 Me Me CH.sub.24-Cl 5-CN CO.sub.2 Me Me CH.sub.24-Br 5-CN CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 5-CN CO.sub.2 Me Me CH.sub.24-OCF.sub.3 5-CN CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-CF.sub.3 CO.sub.2 Me Me CH.sub.24-OCF.sub.3 5-CF.sub.3 CO.sub.2 Me Me CH.sub.24-CF.sub.3 6-F CO.sub.2 Me Me CH.sub.24-Cl 6-F CO.sub.2 Me Me CH.sub.24-Br 6-F CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 6-F CO.sub.2 Me Me CH.sub.24-OCF.sub.3 6-F CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me Et CH.sub.24-Cl 5-Cl CO.sub.2 Me Et CH.sub.24-Br 5-Cl CO.sub.2 Me Et CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me CH.sub.2 Ph CH.sub.24-Cl 5-Cl CO.sub.2 Me CH.sub.2 Ph CH.sub.24-Br 5-Cl CO.sub.2 Me CH.sub.2 Ph CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me allyl CH.sub.24-Cl 5-Cl CO.sub.2 Me allyl CH.sub.24-Br 5-Cl CO.sub.2 Me allyl CH.sub.24-CF.sub.3 5-F CO.sub.2 Et Me CH.sub.24-Cl 5-F CO.sub.2 Et Me CH.sub.24-Br 5-F CO.sub.2 Et Me CH.sub.24-CF.sub.3 5-F CO.sub.2 CH.sub.2 CF.sub.3 Me CH.sub.24-Cl 5-F CO.sub.2 CH.sub.2 CF.sub.3 Me CH.sub.24-Br 5-F CO.sub.2 CH.sub.2 CF.sub.3 Me CH.sub.24-CF.sub.3 5-F CO.sub.2 Ph Me CH.sub.24-Cl 5-F CO.sub.2 Ph Me CH.sub.24-Br 5-F CO.sub.2 Ph Me CH.sub.24-CF.sub.3 5-Cl CO.sub.2 H H CH.sub.24-CF.sub.3 5-Cl CONHMe H CH.sub.24-CF.sub.3 5-Cl CONMe H CH.sub.24-CF.sub.3 5-Cl CONHPh H CH.sub.24-CF.sub.3 5-Cl CSNMe H CH.sub.24-CF.sub.3 5-Cl propargyl Me CH.sub.24-CF.sub.3 5-Cl CH.sub.2 CH.sub.2 CN Me CH.sub.24-CF.sub.3 5-Cl CH.sub.2 CO.sub.2 Me Me CH.sub.24-CF.sub.3 5-Cl CH.sub.2 CMe Me CH.sub.24-CF.sub.3 5-Cl OMe H CH.sub.24-CF.sub.3 5-Cl SMe H CH.sub.24-CF.sub.3 5-Cl SO.sub.2 Me H CH.sub.24-CF.sub.3 5-Cl C(O)Me Me CH.sub.24-CF.sub.3 5-Cl C(O)Et Me CH.sub.24-CF.sub.3 5-Cl C(O)Me H CH.sub.24-CF.sub.3 5-Cl C(O)Et H CH.sub.24-CF.sub.3 5-Cl CN Me CH.sub.24-CF.sub.3 5-Cl CN Et CH.sub.24-CF.sub.3 5-Cl CN CH.sub.2 Ph CH.sub.24-CF.sub.3 5-Cl CN H CH.sub.24-CF.sub.3 H H H CH.sub.2 CH.sub.24-Cl H H H CH.sub.2 CH.sub.24-Br H H H CH.sub.2 CH.sub.24-OCF.sub.2 H H H H CH.sub.2 CH.sub.24-CF.sub.3 4-F H H CH.sub.2 CH.sub.24-Cl 4-F H H CH.sub.2 CH.sub.24-Br 4-F H H CH.sub.2 CH.sub.24-OCF.sub.2 H 4-F H H CH.sub.2 CH.sub.24-CF.sub.3 4-Cl H H CH.sub.2 CH.sub.24-Cl 4-Cl H H CH.sub.2 CH.sub.24-Br 4-Cl H H CH.sub.2 CH.sub.24-OCF.sub.2 H 4-Cl H H CH.sub.2 CH.sub.24-CF.sub.3 5-F H H CH.sub.2 CH.sub.24-Cl 5-F H H CH.sub.2 CH.sub.24-Br 5-F H H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F H H CH.sub.2 CH.sub.24-CF.sub.3 6-F H H CH.sub.2 CH.sub.24-Cl 6-F H H CH.sub.2 CH.sub.24-Br 6-F H H CH.sub.2 CH.sub.24-OCF.sub.2 H 6-F H H CH.sub.2 CH.sub.24-CF.sub.3 6-Cl H H CH.sub.2 CH.sub.24-Cl 6-Cl H H CH.sub.2 CH.sub.24-Br 6-Cl H H CH.sub.2 CH.sub.24-OCF.sub.2 H 6-Cl H H CH.sub.2 CH.sub.24-CF.sub.3 4-F Me H CH.sub.2 CH.sub.24-Cl 4-F Me H CH.sub.2 CH.sub.24-Br 4-F Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 4-F Me H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Me H CH.sub.2 CH.sub.24-Cl 5-Cl Me H CH.sub.2 CH.sub.24-Br 5-Cl Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl Me H CH.sub.2 CH.sub.24-CF.sub.3 5-OCF.sub.2 H Me H CH.sub.2 CH.sub.24-Cl 5-OCF.sub.2 H Me H CH.sub.2 CH.sub.24-Br 5-OCF.sub.2 H Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H Me H CH.sub.2 CH.sub.24-CF.sub.3 5-F Me H CH.sub.2 CH.sub.24-Cl 5-F Me H CH.sub.2 CH.sub.24-Br 5-F Me H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Et H CH.sub.2 CH.sub.24-Cl 5-Cl Et H CH.sub.2 CH.sub.24-Br 5-Cl Et H CH.sub.2 CH.sub.24-CF.sub.3 5-OCF.sub.2 H Et H CH.sub.2 CH.sub.24-Cl 5-OCF.sub.2 H Et H CH.sub.2 CH.sub.24-Br 5-OCF.sub.2 H Et H CH.sub.2 CH.sub.24-CF.sub.3 5-F n-Bu H CH.sub.2 CH.sub.24-Cl 5-F n-Bu H CH.sub.2 CH.sub.24-Br 5-F n-Bu H CH.sub.2 CH.sub.24-CF.sub.3 4-F n-Bu H CH.sub.2 CH.sub.24-Cl 4-F n-Bu H CH.sub.2 CH.sub.24-Br 4-F n-Bu H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl allyl H CH.sub.2 CH.sub.24-Cl 5-Cl allyl H CH.sub.2 CH.sub.24-Br 5-Cl allyl H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Me Me CH.sub.2 CH.sub.24-Cl 5-Cl Me Me CH.sub.2 CH.sub.24-Br 5-Cl Me Me CH.sub.2 CH.sub.24-CF.sub.3 5-F Me Me CH.sub.2 CH.sub.24-Cl 5-F Me Me CH.sub.2 CH.sub.24-Br 5-F Me Me CH.sub.2 CH.sub.24-CF.sub.3 5-OCF.sub.2 H Me Me CH.sub.2 CH.sub.24-Cl 5-OCF.sub.2 H Me Me CH.sub.2 CH.sub.24-Br 5-OCF.sub.2 H Me Me CH.sub.2 CH.sub.24-CF.sub.3 5-OCF.sub.3 Me Me CH.sub. 2 CH.sub.24-Cl 5-OCF.sub.3 Me Me CH.sub.2 CH.sub.24-Br 5-OCF.sub.3 Me Me CH.sub.2 CH.sub.24-CF.sub.3 4-F Me Me CH.sub.2 CH.sub.24-Cl 4-F Me Me CH.sub.2 CH.sub.24-Br 4-F Me Me CH.sub.2 CH.sub.24-CF.sub.3 5-Br Me Me CH.sub.2 CH.sub.24-Cl 5-Br Me Me CH.sub.2 CH.sub.24-Br 5-Br Me Me CH.sub.2 CH.sub.24-CF.sub.3 5-Cl CH.sub.2 Ph H CH.sub.2 CH.sub.24-Cl 5-Cl CH.sub.2 Ph H CH.sub.2 CH.sub.24-Br 5-Cl CH.sub.2 Ph H CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl CH.sub.2 Ph H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl CH.sub.2 Ph H CH.sub.2 CH.sub.24-CF.sub.3 5-F CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-Cl 5-F CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-Br 5-F CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-OCF.sub.3 5-F CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-CF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-Cl 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-Br 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-OCF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H CH.sub.2 Ph-4-F H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.2 CH.sub.24-Cl 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.2 CH.sub.24-Br 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl CH.sub.2 Ph-4-Cl H CH.sub.2 CH.sub.24-CF.sub.3 H CO.sub.2 Me H CH.sub.2 CH.sub.24-Cl H CO.sub.2 Me H CH.sub.2 CH.sub.24-Br H CO.sub.2 Me H CH.sub.2 CH.sub.24-OCF.sub.2 H H CO.sub.2 Me H CH.sub.2 CH.sub.24-F H CO.sub.2 Me H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-Cl 5-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-Br 5-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-NO.sub.2 5-Cl CO.sub.2 Me N CH.sub.2 CH.sub.24-CF.sub.3 5-F CO.sub.2 Me H CH.sub.2 CH.sub.24-Cl 5-F CO.sub.2 Me H CH.sub.2 CH.sub.24-Br 5-F CO.sub.2 Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F CO.sub.2 Me H CH.sub.2 CH.sub.24-OCF.sub.3 5-F CO.sub.2 Me H CH.sub.2 CH.sub.24-CN 5-F CO.sub.2 Me H CH.sub.2 CH.sub.24-CF.sub.3 4-F CO.sub.2 Me H CH.sub.2 CH.sub.24-Cl 4-F CO.sub.2 Me H CH.sub.2 CH.sub.24-Br 4-F CO.sub.2 Me H CH.sub.2 CH.sub.24-CF.sub.3 4-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-Cl 4-Cl CO.sub.2 Me E CH.sub.2 CH.sub.24-Br 4-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.24-Cl 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.24-Br 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.23,4-CF.sub.2 C(Me).sub.2 O 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.24-CF.sub.3 5-F CO.sub.2 Me Me CH.sub.2 CH.sub.24-Cl 5-F CO.sub.2 Me Me CH.sub.2 CH.sub.24-Br 5-F CO.sub.2 Me Me CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F CO.sub.2 Me Me CH.sub.2 CH.sub.24-OCF.sub.3 5-F CO.sub.2 Me Me CH.sub.2 CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-F CO.sub.2 Me Me CH.sub.2 CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-F CO.sub.2 Me Me CH.sub.2 CH.sub.24-CF.sub.3 H H H O4-Cl H H H O4-Br H H H O4-OCF.sub.3 H H H O4-OCF.sub.2 H H H H O4-CF.sub.3 4-F H H O4-Cl 4-F H H O4-Br 4-F H H O4-OCF.sub.3 4-F H H O4-OCF.sub.2 H 4-F H H O4-CF.sub.3 4-Cl H H O4-Cl 4-Cl H H O4-Br 4-Cl H H O4-OCF.sub.3 4-Cl H H O4-OCF.sub.2 H 4-Cl H H O4-CF.sub.3 5-F H H O4-Cl 5-F H H O4-Br 5-F H H O4-OCF.sub.3 5-F H H O4-OCF.sub.2 H 5-F H H O4-CF.sub.3 6-F H H O4-CF.sub.3 4-F Me H O4-Cl 4-F Me H O4-Br 4-F Me H O4-OCF.sub.3 4-F He H O4-OCF.sub.2 H 4-F Me H O4-CF.sub.3 5-Cl Me H O4-Cl 5-Cl Me H O4-Br 5-Cl Me H O4-OCF.sub.3 5-Cl Me H O4-OCF.sub.2 H 5-Cl Me H O4-CF.sub.3 5-OCF.sub.2 H Me H O4-Cl 5-OCF.sub.2 H Me H O4-Br 5-OCF.sub.2 H Me H O4-OCF.sub.3 5-OCF.sub.2 H Me H O4-OCF.sub.2 H 5-OCF.sub.2 H Me H O4-CF.sub.3 5-CF.sub.3 Me H O4-Cl 5-CF.sub.3 Me H O4-Br 5-CF.sub.3 Me H O4-OCF.sub.3 5-CF.sub.3 Me H O4-OCF.sub.2 H 5-CF.sub.3 Me H O4-CH.sub.3 5-F Me H O4-Cl 5-F Me H O4-Br 5-F Me H O4-OCF.sub.3 5-F Me H O4-CF.sub.3 5-Cl Et H O4-Cl 5-Cl Et H O4-Br 5-Cl Et H O4-CF.sub.3 5-OCF.sub.2 H Et H O4-Cl 5-OCF.sub.2 H Et H O4-Br 5-OCF.sub.2 H Et H O4-CF.sub.3 5-F n-Bu H O4-Cl 5-F n-Bu H O4-Br 5-F n-Bu H O4-CF.sub.3 4-F n-Bu H O4-Cl 4-F n-Bu H O4-Br 4-F n-Bu H O4-CF.sub.3 5-Cl allyl H O4-Cl 5-Cl allyl H O4-Br 5-Cl allyl H O4-CF.sub.3 5-Cl Me Me O4-Cl 5-Cl Me Me O4-Br 5-Cl Me Me O4-CF.sub.3 5-F Me Me O4-Cl 5-F Me Me O4-Br 5-F Me Me O4-CF.sub.3 5-OCF.sub.2 H Me Me O4-Cl 5-OCF.sub.2 H Me Me O4-Br 5-OCF.sub.2 H Me Me O4-CF.sub.3 5-OCF.sub.3 Me Me O4-Cl 5-OCF.sub.3 Me Me O4-Br 5-OCF.sub.3 Me Me O4-CF.sub.3 4-F Me Me O4-Cl 4-F Me Me O4-Br 4-F Me Me O4-CF.sub.3 5-Br Me Me O4-Cl 5-Br Me Me O4-Br 5-Br Me Me O4-OCF.sub.3 5-Cl allyl Me O4-CF.sub.3 5-F allyl Me O4-OCF.sub.3 5-F allyl Me O4-CF.sub.3 5-F Et Me O4-OCF.sub.3 5-F Et Me O4-CF.sub.3 5-Cl Et Me O4-OCF.sub.3 5-Cl Et Me O4-CF.sub.3 5-CF.sub.3 Et Me O4-CF.sub.3 5-CF.sub.3 allyl Me O4-OCF.sub.3 5-CF.sub.3 allyl Me O4-CF.sub.3 5-F CH.sub.2 Ph Me O4-OCF.sub.3 5-F CH.sub.2 Ph Me O4-CF.sub.3 5-Cl CH.sub.2 Ph Me O4-OCF.sub.3 5-Cl CH.sub.2 Ph Me O4-CF.sub.3 5-Cl CH.sub.2 Ph H O4-Cl 5-Cl CH.sub.2 Ph H O4-Br 5-Cl CH.sub.2 Ph H O4-CF.sub.3 5-Cl CH.sub.2 Ph H O4-OCF.sub.2 H 5-Cl CH.sub.2 Ph H O4-CF.sub.3 5-F CH.sub.2 Ph-4-F H O4-Cl 5-F CH.sub.2 Ph-4-F H O4-Br 5-F CH.sub.2 Ph-4-F H O4-OCF.sub.2 H 5-F CH.sub.2 Ph-4-F H O4-OCF.sub.3 5-F CH.sub.2 Ph-4-F H O4-CF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-F H O4-Cl 5-OCF.sub.2 H CH.sub.2 Ph-4-F H O4-Br 5-OCF.sub.2 H CH.sub.2 Ph-4-F H O4-OCF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-F H O4-OCF.sub.2 H 5-OCF.sub.2 H CH.sub.2 Ph-4-F H O4-CF.sub.3 5-Cl CH.sub.2 Ph-4-Cl H O4-Cl 5-Cl CH.sub.2 Ph-4-Cl H O4-Br 5-Cl CH.sub.2 Ph-4-Cl H O4-OCF.sub.3 5-Cl CH.sub.2 Ph-4-Cl H O4-OCF.sub.2 H 5-Cl CH.sub.2 Ph-4-Cl H O4-CF.sub.3 H CO.sub.2 Me H O4-Cl H CO.sub.2 Me H O4-Br H CO.sub.2 Me H O4-OCF.sub.2 H H CO.sub.2 Me H O4-F H CO.sub.2 Me H O4-CF.sub.3 5-Cl CO.sub.2 Me H O4-Cl 5-Cl CO.sub.2 Me H O4-Br 5-Cl CO.sub.2 Me H O4-OCF.sub.2 H 5-Cl CO.sub.2 Me H O4-OCF.sub.3 5-Cl CO.sub.2 Me H O4-NO.sub.2 5-Cl CO.sub.2 Me H O4-CF.sub.3 5-F CO.sub.2 Me H O4-Cl 5-F CO.sub.2 Me H O4-Br 5-F CO.sub.2 Me H O4-OCF.sub.2 H 5-F CO.sub.2 Me H O4-OCF.sub.3 5-F CO.sub.2 Me H O4-CN 5-F CO.sub.2 Me H O4-CF.sub.3 4-F CO.sub.2 Me H O4-Cl 4-F CO.sub.2 Me H O4-Br 4-F CO.sub.2 Me H O4-CF.sub.3 4-Cl CO.sub.2 Me H O4-Cl 4-Cl CO.sub.2 Me H O4-Br 4-Cl CO.sub.2 Me H O4-CF.sub.3 H CO.sub.2 Me Me O4-Cl H CO.sub.2 Me Me O4-Br H CO.sub.2 Me Me O4-OCF.sub.2 H H CO.sub.2 Me Me O4-OCF.sub.3 H CO.sub.2 Me Me O4-CF.sub.3 5-Cl CO.sub.2 Me Me O4-Cl 5-Cl CO.sub.2 Me Me O4-Br 5-Cl CO.sub.2 Me Me O4-OCF.sub.2 H 5-Cl CO.sub.2 Me Me O4-OCF.sub.3 5-Cl CO.sub.2 Me Me O4-CF.sub.3 5-F CO.sub.2 Me Me O4-Cl 5-F CO.sub.2 Me Me O4-Br 5-F CO.sub.2 Me Me O4-OCF.sub.2 H 5-F CO.sub.2 Me Me O4-OCF.sub.3 5-F CO.sub.2 Me Me O4-CF.sub.3 4-F CO.sub.2 Me Me O4-Cl 4-F CO.sub.2 Me Me O4-Br 4-F CO.sub.2 Me Me O4-OCF.sub.3 4-F CO.sub.2 Me Me O4-OCF.sub.2 H 4-F CO.sub.2 Me Me O3,4-CF.sub.2 CF.sub.2 O 4-F CO.sub.2 Me Me O3,4-CH.sub.2 C(Me).sub.2 O 4-F CO.sub.2 Me Me O4-CF.sub.3 5-CF.sub.3 CO.sub.2 Me Me O4-Cl 5-CF.sub.3 CO.sub.2 Me Me O4-Br 5-CF.sub.3 CO.sub.2 Me Me O4-OCF.sub.3 5-CF.sub.3 CO.sub.2 Me Me O4-OCF.sub.2 H 5-CF.sub.3 CO.sub.2 Me Me O4-CF.sub.3 5-Br CO.sub.2 Me Me O4-Cl 5-Br CO.sub.2 Me Me O4-Br 5-Br CO.sub.2 Me Me O4-OCF.sub.3 5-Br CO.sub.2 Me Me O4-OCF.sub.2 H 5-Br CO.sub.2 Me Me O3,4-CF.sub.2 CF.sub.2 O 5-Br CO.sub.2 Me Me O3,4-CH.sub.2 C(Me).sub.2 O 5-Br CO.sub.2 Me Me O4-CF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me O4-Cl 5-OCF.sub.2 H CO.sub.2 Me Me O4-Br 5-OCF.sub.2 H CO.sub.2 Me Me O4-OCF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me O4-OCF.sub.2 H 5-OCF.sub.2 H CO.sub.2 Me Me O4-CF.sub.3 5-Cl CO.sub.2 Me Et O4-Cl 5-Cl CO.sub.2 Me Et O4-Br 5-Cl CO.sub.2 Me Et O4-CF.sub.3 5-Cl CO.sub.2 Me CH.sub.2 Ph O4-Cl 5-Cl CO.sub.2 Me CH.sub.2 Ph O4-Br 5-Cl CO.sub.2 Me CH.sub.2 Ph O4-CF.sub.3 5-Cl CO.sub.2 Me allyl O4-Cl 5-Cl CO.sub. 2 Me allyl O4-Br 5-Cl CO.sub.2 Me allyl O4-CF.sub.3 5-F CO.sub.2 Et Me O4-Cl 5-F CO.sub.2 Et Me O4-Br 5-F CO.sub.2 Et Me O4-CF.sub.3 5-F CO.sub.2 CH.sub.2 CF.sub.3 Me O4-Cl 5-F CO.sub.2 CH.sub.2 CF.sub.3 Me O4-Br 5-F CO.sub.2 CH.sub.2 CF.sub.3 Me O4-CF.sub.3 5-F CO.sub.2 Ph Me O4-Cl 5-F CO.sub.2 Ph Me O4-Br 5-F CO.sub.2 Ph Me O4-CF.sub.3 5-Cl CO.sub.2 H R O4-CF.sub.3 5-Cl CONHMe H O4-CF.sub.3 5-Cl CONMe H O4-CF.sub.3 5-Cl CONHPh H O4-CF.sub.3 5-Cl CSNMe.sub.2 H O4-CF.sub.3 5-Cl propargyl Me O4-CF.sub.3 5-Cl CH.sub.2 CH.sub.2 CN Me O4-CF.sub.3 5-Cl CH.sub.2 CO.sub.2 Me Me O4-CF.sub.3 5-Cl CH.sub.2 OMe Me O4-CF.sub.3 5-Cl OMe H O4-CF.sub.3 5-Cl SMe H O4-CF.sub.3 5-Cl SO.sub.2 Me H O4-CF.sub.3 5-Cl C(O)Me Me O4-CF.sub.3 5-Cl C(O)Et Me O4-CF.sub.3 5-Cl C(O)Me H O4-CF.sub.3 5-Cl C(O)Et H O4-CF.sub.3 5-Cl CN Me O4-CF.sub.3 5-Cl CN Et O4-CF.sub.3 5-Cl CN CH.sub.2 Ph O4-CF.sub.3 5-Cl CN H O4-CF.sub.3 H H H S4-Cl H H H S4-Br H H H S4-OCF.sub.2 H H H H S4-CF.sub.3 4-F H H S4-Cl 4-F H H S4-Br 4-F H H S4-OCF.sub.2 H 4-F H H S4-CF.sub.3 4-Cl H H S4-Cl 4-Cl H H S4-Br 4-Cl H H S4-OCF.sub.2 H 4-Cl H H S4-CF.sub.3 5-F H H S4-Cl 5-F H H S4-Br 5-F H H S4-OCF.sub.2 H 5-F H H S4-CF.sub.3 4-F Me H S4-Cl 4-F Me H S4-Br 4-F Me H S4-OCF.sub.2 H 4-F Me H S4-CF.sub.3 5-Cl Me H S4-Cl 5-Cl Me H S4-Br 5-Cl Me H S4-OCF.sub.2 H 5-Cl Me H S4-CF.sub.3 5-OCF.sub.2 H Me H S4-Cl 5-OCF.sub.2 H Me H S4-Br 5-OCF.sub.2 H Me H S4-OCF.sub.2 H 5-OCF.sub.2 H Me H S4-CF.sub.3 5-F Me H S4-Cl 5-F Me H S4-Br 5-F Me H S4-CF.sub.3 5-Cl Et H S4-Cl 5-Cl Et H S4-Br 5-Cl Et H S4-CF.sub.3 5-OCF.sub.2 H Et H S4-Cl 5-OCF.sub.2 H Et H S4-Br 5-OCF.sub.2 H Et H S4-CF.sub.3 5-F n-Bu H S4-Cl 5-F n-Bu H S4-Br 5-F n-Bu H S4-CF.sub.3 4-F n-Bu H S4-Cl 4-F n-Bu H S4-Br 4-F n-Bu H S4-CF.sub.3 5-Cl allyl H S4-Cl 5-Cl allyl H S4-Br 5-Cl allyl H S4-CF.sub.3 5-Cl Me Me S4-Cl 5-Cl Me Me S4-Br 5-Cl Me Me S4-CF.sub.3 5-F Me Me S4-Cl 5-F Me Me S4-Br 5-F Me Me S4-CF.sub.3 5-OCF.sub.2 H Me Me S4-Cl 5-OCF.sub.2 H Me Me S4-Br 5-OCF.sub.2 H Me Me S4-CF.sub.3 5-OCF.sub.3 Me Me S4-Cl 5-OCF.sub.3 Me Me S4-Br 5-OCF.sub.3 Me Me S4-CF.sub.3 4-F Me Me S4-Cl 4-F Me Me S4-Br 4-F Me Me S4-CF.sub.3 5-Br Me Me S4-Cl 5-Br Me Me S4-Br 5-Br Me Me S4-CF.sub. 3 5-Cl CH.sub.2 Ph H S4-Cl 5-Cl CH.sub.2 Ph H S4-Br 5-Cl CH.sub.2 Ph H S4-OCF.sub.3 5-Cl CH.sub.2 Ph H S4-OCF.sub.2 H 5-Cl CH.sub.2 Ph H S4-CF.sub.3 5-F CH.sub.2 Ph-4-F H S4-Cl 5-F CH.sub.2 Ph-4-F H S4-Br 5-F CH.sub.2 Ph-4-F H S4-OCF.sub.2 H 5-F CH.sub.2 Ph-4-F H S4-OCF.sub.3 5-F CH.sub.2 Ph-4-F H S4-CF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-F H S4-Cl 5-OCF.sub.2 H CH.sub.2 Ph-4-F H S4-Br 5-OCF.sub.2 H CH.sub.2 Ph-4-F H S4-OCF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-F H S4-OCF.sub.2 H 5-OCF.sub.2 H CH.sub.2 Ph-4-F H S4-CF.sub.3 5-Cl CH.sub.2 Ph-4-Cl H S4-Cl 5-Cl CH.sub.2 Ph-4-Cl H S4-Br 5-Cl CH.sub.2 Ph-4-Cl H S4-OCH.sub.3 5-Cl CH.sub.2 Ph-4-Cl H S4-OCF.sub.2 H 5-Cl CH.sub.2 Ph-4-Cl H S4-CF.sub.3 H CO.sub.2 Me H S4-Cl H CO.sub.2 Me H S4-Br H CO.sub.2 Me H S4-OCF.sub.2 H H CO.sub.2 Me H S4-F H CO.sub.2 Me H S4-CF.sub.3 5-Cl CO.sub.2 Me H S4-Cl 5-Cl CO.sub.2 Me H S4-Br 5-Cl CO.sub.2 Me H S4-OCF.sub.2 H 5-Cl CO.sub.2 Me H S4-OCF.sub.3 5-Cl CO.sub.2 Me H S4-NO.sub.2 5-Cl CO.sub.2 Me H S4-CH.sub.3 5-F CO.sub.2 Me H S4-Cl 5-F CO.sub.2 Me H S4-Br 5-F CO.sub.2 Me H S4-OCF.sub.2 H 5-F CO.sub.2 Me H S4-OCF.sub.3 5-F CO.sub.2 Me H S4-CN 5-F CO.sub.2 Me H S4-CF.sub.3 4-F CO.sub.2 Me H S4-Cl 4-F CO.sub.2 Me H S4-Br 4-F CO.sub.2 Me H S4-CF.sub.3 4-Cl CO.sub.2 Me H S4-Cl 4-Cl CO.sub.2 Me H S4-Br 4-Cl CO.sub.2 Me H S4-CF.sub.3 H CO.sub.2 Me Me S4-Cl H CO.sub.2 Me Me S4-Br H CO.sub.2 Me Me S4-OCF.sub.2 H H CO.sub.2 Me Me S4-OCF.sub.3 H CO.sub.2 Me Me S3,4-CF.sub.2 CF.sub.2 O H CO.sub.2 Me Me S3,4-CH.sub.2 C(Me).sub.2 O H CO.sub.2 Me Me S4-CF.sub.3 5-Cl CO.sub.2 Me Me S4-Cl 5-Cl CO.sub.2 Me Me S4-Br 5-Cl CO.sub.2 Me Me S4-OCF.sub.2 H 5-Cl CO.sub.2 Me Me S4-OCF.sub.3 5-Cl CO.sub.2 Me Me S3,4-CF.sub.2 CF.sub.2 O 5-Cl CO.sub.2 Me Me S3,4-CF.sub.2 C(Me).sub.2 O 5-Cl CO.sub.2 Me Me S4-CF.sub.3 5-F CO.sub.2 Me Me S4-Cl 5-F CO.sub.2 Me Me S4-Br 5-F CO.sub.2 Me Me S4-OCF.sub.2 H 5-F CO.sub.2 Me Me S4-OCF.sub.3 5-F CO.sub.2 Me Me S3,4-CF.sub.2 CF.sub.2 O 5-F CO.sub.2 Me Me S3,4-CH.sub.2 C(Me).sub.2 O 5-F CO.sub.2 Me Me S4-CF.sub.3 4-F CO.sub.2 Me Me S4-Cl 4-F CO.sub.2 Me Me S4-Br 4-F CO.sub.2 Me Me S4-OCF.sub.3 4-F CO.sub.2 Me Me S4-OCF.sub.2 H 4-F CO.sub.2 Me Me S3,4-CF.sub.2 CF.sub.2 O 4-F CO.sub.2 Me Me S3,4-CH.sub.2 C(Me).sub.2 O 4-F CO.sub.2 Me Me S4-CF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me S4-Cl 5-OCF.sub.2 H CO.sub.2 Me Me S4-Br 5-OCF.sub.2 H CO.sub.2 Me Me S4-OCF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me S4-OCF.sub.2 H 5-OCF.sub.2 H CO.sub.2 Me Me S3,4-CF.sub.2 CF.sub.2 O 5-OCF.sub.2 H CO.sub.2 Me Me S3,4-CH.sub.2 C(Me).sub.2 O 5-OCF.sub.2 H CO.sub.2 Me Me S4-OCF.sub.2 H 6-F CO.sub.2 Me Me S4-OCF.sub.3 6-F CO.sub.2 Me Me S4-CF.sub.3 5-Cl CO.sub.2 Me Et S4-Cl 5-Cl CO.sub.2 Me Et S4-Br 5-Cl CO.sub.2 Me Et S4-CF.sub.3 5-Cl CO.sub.2 Me CH.sub.2 Ph S4-Cl 5-Cl CO.sub.2 Me CH.sub.2 Ph S4-Br 5-Cl CO.sub.2 Me CH.sub.2 Ph S4-CF.sub.3 5-Cl CO.sub.2 Me allyl S4-Cl 5-Cl CO.sub.2 Me allyl S4-Br 5-Cl CO.sub.2 Me allyl S4-CF.sub.3 5-F CO.sub.2 Et Me S4-Cl 5-F CO.sub.2 Et Me S4-Br 5-F CO.sub.2 Et Me S4-CF.sub.3 5-F CO.sub.2 CH.sub.2 CF.sub.3 Me S4-Cl 5-F CO.sub.2 CH.sub.2 CF.sub.3 Me S4-Br 5-F CO.sub.2 CH.sub.2 CF.sub.3 Me S4-CF.sub.3 5-F CO.sub.2 Ph Me S4-Cl 5-F CO.sub.2 Ph Me S4-Br 5-F CO.sub.2 Ph Me S4-CF.sub.3 5-Cl CO.sub.2 H H S4-CF.sub.3 5-Cl CONHMe H S4-CF.sub.3 5-Cl CONMe H S4-CF.sub.3 5-Cl CONHPh H S4-CF.sub.3 5-Cl CSNMe.sub.2 H S4-CF.sub.3 5-Cl propargyl Me S4-CF.sub.3 5-Cl CH.sub.2 CH.sub.2 CN Me S4-CF.sub.3 5-Cl CH.sub.2 CO.sub.2 Me Me S4-CF.sub.3 5-Cl CH.sub.2 OMe Me S4-CF.sub.3 5-Cl OMe H S4-CF.sub.3 5-Cl SMe H S4-CF.sub.3 5-Cl SO.sub.2 Me H S4-CF.sub.3 5-Cl C(O)Me Me S4-CF.sub.3 5-Cl C(O)Et Me S4-CF.sub.3 5-Cl C(O)Me H S4-CF.sub.3 5-Cl C(O)Et H S4-CF.sub.3 5-Cl CN Me S4-CF.sub.3 5-Cl CN Et S4-CF.sub.3 5-Cl CN CH.sub.2 Ph S4-CF.sub.3 5-Cl CN H S4-CF.sub.3 4-F allyl H OCH.sub.24-Cl 4-F allyl H OCH.sub.24-Br 4-F allyl H OCH.sub.24-OCF.sub.2 H 4-F allyl H OCH.sub.24-OCF.sub.3 4-F allyl H OCH.sub.24-CF.sub.3 4-Cl allyl H OCH.sub. 24-Cl 4-Cl allyl H OCH.sub.24-Br 4-Cl allyl H OCH.sub.24-OCF.sub.2 H 4-Cl allyl H OCH.sub.24-OCF.sub.3 4-Cl allyl H OCH.sub.24-CF.sub.3 5-F propargyl H OCH.sub.24-Cl 5-F propargyl H OCH.sub.24-Br 5-F propargyl H OCH.sub.24-OCF.sub.2 H 5-F propargyl H OCH.sub.24-OCF.sub.3 5-F propargyl H OCH.sub.24-CF.sub.3 5-Cl Me H OCH.sub.24-Cl 5-Cl Me H OCH.sub.24-Br 5-Cl Me H OCH.sub.24-OCF.sub.2 H 5-Cl Me H OCH.sub.24-OCF.sub.3 5-Cl Me H OCH.sub.24-CF.sub.3 5-CF.sub.3 Me H OCH.sub.24-Cl 5-CF.sub.3 Me H OCH.sub.24-Br 5-CF.sub.3 Me H OCH.sub.24-OCF.sub.2 H 5-CF.sub.3 Me H OCH.sub.24-OCF.sub.3 5-CF.sub.3 Me H OCH.sub.24-CF.sub.3 5-OCF.sub.2 H Me H OCH.sub.24-Cl 5-OCF.sub.2 H Me H OCH.sub.24-Or 5-OCF.sub.2 H Me H OCH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H Me H OCH.sub.24-OCF.sub.3 5-OCF.sub.2 H Me H OCH.sub.24-CF.sub.3 4-F CH.sub.2 Ph H OCH.sub.24-Cl 4-F CH.sub.2 Ph H OCH.sub.24-Br 4-F CH.sub.2 Ph H OCH.sub.24-OCF.sub.2 H 4-F CH.sub.2 Ph H OCH.sub.24-OCF.sub.3 4-F CH.sub.2 Ph H OCH.sub.24-CF.sub.3 4-Cl CH.sub.2 Ph H OCH.sub.24-Cl 4-Cl CH.sub.2 Ph H OCH.sub.24-Br 4-Cl CH.sub.2 Ph H OCH.sub.24-OCF.sub.2 H 4-Cl CH.sub.2 Ph H OCH.sub.24-OCF.sub.3 4-Cl CH.sub.2 Ph H OCH.sub.24-CF.sub.3 5-F CH.sub.2 Ph H OCH.sub.24-Cl 5-F CH.sub.2 Ph H OCH.sub.24-Br 5-F CH.sub.2 Ph H OCH.sub.24-OCF.sub.2 H 5-F CH.sub.2 Ph H OCH.sub.24-OCF.sub.3 5-F CH.sub.2 Ph H OCH.sub.24-CF.sub.3 5-Cl CH.sub.2 Ph-4-Cl H OCH.sub.24-Cl 5-Cl CH.sub.2 Ph-4-Cl H OCH.sub.24-Br 5-Cl CH.sub.2 Ph-4-Cl H OCH.sub.24-OCF.sub.2 H 5-Cl CH.sub.2 Ph-4-Cl H OCH.sub.24-OCF.sub.3 5-Cl CH.sub.2 Ph-4-Cl H OCH.sub.24-CF.sub.3 5-CF.sub.3 CH.sub.2 Ph-4-Cl H OCH.sub.24-Cl 5-CF.sub.3 CH.sub.2 Ph-4-Cl H OCH.sub.24-Br 5-CF.sub.3 CH.sub.2 Ph-4-Cl H OCH.sub.24-OCF.sub.2 H 5-CF.sub.3 CH.sub.2 Ph-4-Cl H OCH.sub.24-OCF.sub.3 5-CF.sub.3 CH.sub.2 Ph-4-Cl H OCH.sub.24-CF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H OCH.sub.24-Cl 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H OCH.sub.24-Br 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H OCH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H OCH.sub.24-OCF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H OCH.sub.24-CF.sub.3 4-F CO.sub.2 Me H OCH.sub.24-Cl 4-F CO.sub.2 Me H OCH.sub.24-Br 4-F CO.sub.2 Me H OCH.sub.24-OCF.sub.2 H 4-F CO.sub.2 Me H OCH.sub.24-OCF.sub.3 4-F CO.sub.2 Me H OCH.sub.24-CF.sub.3 4-Cl CO.sub.2 Me H OCH.sub.24-Cl 4-Cl CO.sub.2 Me H OCH.sub.24-Br 4-Cl CO.sub.2 Me H OCH.sub.24-OCF.sub.2 H 4-Cl CO.sub.2 Me H OCH.sub.24-OCF.sub.3 4-Cl CO.sub.2 Me H OCH.sub.24-CF.sub.3 5-F CO.sub.2 Me H OCH.sub.24-Cl 5-F CO.sub.2 Me H OCH.sub.24-Br 5-F CO.sub.2 Me H OCH.sub.24-OCF.sub.2 H 5-F CO.sub.2 Me H OCH.sub.24-OCF.sub.3 5-F CO.sub.2 Me H OCH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me H OCH.sub.24-Cl 5-Cl CO.sub.2 Me H OCH.sub.24-Br 5-Cl CO.sub.2 Me H OCH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me H OCH.sub.24-OCF.sub.3 5-Cl CO.sub.2 Me H OCH.sub.24-CF.sub.3 5-CF.sub.3 CO.sub.2 Me H OCH.sub.24-Cl 5-CF.sub.3 CO.sub.2 Me H OCH.sub.24-Br 5-CF.sub.3 CO.sub.2 Me H OCH.sub.24-OCF.sub.2 H 5-CF.sub.3 CO.sub.2 Me H OCH.sub.24-OCF.sub.3 5-CF.sub.3 CO.sub.2 Me H OCH.sub.24-CF.sub.3 5-OCF.sub.2 H CO.sub.2 Me H OCH.sub.24-Cl 5-OCF.sub.2 H CO.sub.2 Me H OCH.sub.24-Br 5-OCF.sub.2 H CO.sub.2 Me H OCH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H CO.sub.2 Me H OCH.sub.24-OCF.sub.3 5-OCF.sub.2 H CO.sub.2 Me H OCH.sub.24-CF.sub.3 4-F CO.sub.2 Me Me OCH.sub.24-Cl 4-F CO.sub.2 Me Me OCH.sub.24-Br 4-F CO.sub.2 Me Me OCH.sub.24-OCF.sub.2 H 4-F CO.sub.2 Me Me OCH.sub.24-OCF.sub.3 4-F CO.sub.2 Me Me OCH.sub.24-CF.sub.3 4-Cl CO.sub.2 Me Me OCH.sub.24-Cl 4-Cl CO.sub.2 Me Me OCH.sub.24-Br 4-Cl CO.sub.2 Me Me OCH.sub.24-OCF.sub.2 H 4-Cl CO.sub.2 Me Me OCH.sub.24-OCF.sub.3 4-Cl CO.sub.2 Me Me OCH.sub.24-CF.sub.3 5-F CO.sub.2 Me Me OCH.sub.24-Cl 5-F CO.sub.2 Me Me OCH.sub.24-Br 5-F CO.sub.2 Me Me OCH.sub.24-OCF.sub.2 H 5-F CO.sub.2 Me Me OCH.sub.24-OCF.sub.3 5-F CO.sub.2 Me Me OCH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me Me OCH.sub.24-Cl 5-Cl CO.sub.2 Me Me OCH.sub.24-Br 5-Cl CO.sub.2 Me Me OCH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me Me OCH.sub.24-OCF.sub.3 5-Cl CO.sub.2 Me Me OCH.sub.24-CF.sub.3 5-CF.sub.3 CO.sub.2 Me Me OCH.sub.24-Cl 5-CF.sub.3 CO.sub.2 Me Me OCH.sub.24-Br 5-CF.sub.3 CO.sub.2 Me Me OCH.sub.24-OCF.sub.2 H 5-CF.sub.3 CO.sub.2 Me Me OCH.sub.24-OCF.sub.3 5-CF.sub.3 CO.sub.2 Me Me OCH.sub.24-CF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me OCH.sub.24-Cl 5-OCF.sub.2 H CO.sub.2 Me Me OCH.sub.24-Br 5-OCF.sub.2 H CO.sub.2 Me Me OCH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H CO.sub. 2 Me Me OCH.sub.24-OCF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me OCH.sub.24-CF.sub.3 4-F Me H SCH.sub.24-Cl 4-F Me H SCH.sub.24-Br 4-F Me H SCH.sub.24-OCF.sub.2 H 4-F Me H SCH.sub.24-OCF.sub.3 4-F Me H SCH.sub.24-CF.sub.3 4-Cl Me H SCH.sub.24-Cl 4-Cl Me H SCH.sub.24-Br 4-Cl Me H SCH.sub.24-OCF.sub.2 H 4-Cl Me H SCH.sub.24-OCF.sub.3 4-Cl Me H SCH.sub.24-CF.sub.3 5-F allyl H SCH.sub.24-Cl 5-F allyl H SCH.sub.24-Br 5-F allyl H SCH.sub.24-OCF.sub.2 H 5-F allyl H SCH.sub.24-OCF.sub.3 5-F allyl H SCH.sub.24-CF.sub.3 5-Cl CH.sub.2 Ph H SCH.sub.24-Cl 5-Cl CH.sub.2 Ph H SCH.sub.24-Br 5-Cl CH.sub.2 Ph H SCH.sub.24-OCF.sub.2 H 5-Cl CH.sub.2 Ph H SCH.sub.24-OCF.sub.3 5-Cl CH.sub.2 Ph H SCH.sub.24-CF.sub.3 5-CF.sub.3 CH.sub.2 Ph-4-Cl H SCH.sub.24-Cl 5-CF.sub.3 CH.sub.2 Ph-4-Cl H SCH.sub.24-Br 5-CF.sub.3 CH.sub.2 Ph-4-Cl H SCH.sub.24-OCF.sub.2 H 5-CF.sub.3 CH.sub.2 Ph-4-Cl H SCH.sub. 24-OCF.sub.3 5-CF.sub.3 CH.sub.2 Ph-4-Cl H SCH.sub.24-CF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H SCH.sub.24-Cl 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H SCH.sub.24-Br 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H SCH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H SCH.sub.24-OCF.sub.3 5-OCF.sub.2 H CH.sub.2 Ph-4-Cl H SCH.sub.24-CF.sub.3 4-F CO.sub.2 Me H SCH.sub.24-Cl 4-F CO.sub.2 Me H SCH.sub.24-Br 4-F CO.sub.2 Me H SCH.sub.24-OCF.sub.2 H 4-F CO.sub.2 Me H SCH.sub.24-OCF.sub.3 4-F CO.sub.2 Me H SCH.sub.24-CF.sub.3 4-Cl CO.sub.2 Me H SCH.sub.24-Cl 4-Cl CO.sub.2 Me H SCH.sub.24-Br 4-Cl CO.sub.2 Me H SCH.sub.24-OCF.sub.2 H 4-Cl CO.sub.2 Me H SCH.sub.24-OCF.sub.3 4-Cl CO.sub.2 Me H SCH.sub.24-CF.sub.3 5-F CO.sub.2 Me H SCH.sub.24-Cl 5-F CO.sub.2 Me H SCH.sub.24-Br 5-F CO.sub.2 Me H SCH.sub.24-OCF.sub.2 H 5-F CO.sub.2 Me H SCH.sub.24-OCF.sub.3 5-F CO.sub.2 Me H SCH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me H SCH.sub.24-Cl 5-Cl CO.sub.2 Me H SCH.sub.24-Br 5-Cl CO.sub.2 Me H SCH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me H SCH.sub.24-OCF.sub.3 5-Cl CO.sub.2 Me H SCH.sub.24-CF.sub.3 5-CF.sub.3 CO.sub.2 Me H SCH.sub.24-Cl 5-CF.sub.3 CO.sub.2 Me H SCH.sub.24-Br 5-CF.sub.3 CO.sub.2 Me H SCH.sub.24-OCF.sub.2 H 5-CF.sub.3 CO.sub.2 Me H SCH.sub.24-OCF.sub.3 5-CF.sub.3 CO.sub.2 Me H SCH.sub.24-CF.sub.3 5-OCF.sub.2 H CO.sub.2 Me H SCH.sub.24-Cl 5-OCF.sub.2 H CO.sub.2 Me H SCH.sub.24-Br 5-OCF.sub.2 H CO.sub.2 Me H SCH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H CO.sub.2 Me H SCH.sub.24-OCF.sub.3 5-OCF.sub.2 H CO.sub.2 Me H SCH.sub.24-CF.sub.3 4-F CO.sub.2 Me Me SCH.sub.24-Cl 4-F CO.sub.2 Me Me SCH.sub.24-Br 4-F CO.sub.2 Me Me SCH.sub.24-OCF.sub.2 H 4-F CO.sub.2 Me Me SCH.sub.24-OCF.sub.3 4-F CO.sub.2 Me Me SCH.sub.24-CF.sub.3 4-Cl CO.sub.2 Me Me SCH.sub.24-Cl 4-Cl CO.sub. 2 Me Me SCH.sub.24-Br 4-Cl CO.sub.2 Me Me SCH.sub.24-OCF.sub.2 H 4-Cl CO.sub.2 Me Me SCH.sub.24-OCF.sub.3 4-Cl CO.sub.2 Me Me SCH.sub.24-CF.sub.3 5-F CO.sub.2 Me Me SCH.sub.24-Cl 5-F CO.sub.2 Me Me SCH.sub.24-Br 5-F CO.sub.2 Me Me SCH.sub.24-OCF.sub.2 H 5-F CO.sub.2 Me Me SCH.sub.24-OCF.sub.3 5-F CO.sub.2 Me Me SCH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me Me SCH.sub.24-Cl 5-Cl CO.sub.2 Me Me SCH.sub.24-Br 5-Cl CO.sub.2 Me Me SCH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me Me SCH.sub.24-OCF.sub.3 5-Cl CO.sub.2 Me Me SCH.sub.24-CF.sub.3 5-CF.sub.3 CO.sub.2 Me Me SCH.sub.24-Cl 5-CF.sub.3 CO.sub.2 Me Me SCH.sub.24-Br 5-CF.sub.3 CO.sub.2 Me Me SCH.sub.24-OCF.sub.2 H 5-CF.sub.3 CO.sub.2 Me Me SCH.sub.24-OCF.sub.3 5-CF.sub.3 CO.sub.2 Me Me SCH.sub.24-CF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me SCH.sub.24-Cl 5-OCF.sub.2 H CO.sub.2 Me Me SCH.sub.24-Br 5-OCF.sub.2 H CO.sub.2 Me Me SCH.sub.24-OCF.sub.2 H 5-OCF.sub.2 H CO.sub.2 Me Me SCH.sub.24-OCF.sub.3 5-OCF.sub.2 H CO.sub.2 Me Me SCH.sub.2______________________________________
TABLE 13__________________________________________________________________________ ##STR21##R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 R.sub.6 A__________________________________________________________________________4-CF.sub.3 5-Cl Ph H Me H CH.sub.24-Cl 5-Cl Ph H Me H CH.sub.24-Br 5-Cl Ph H Me H CH.sub.24-CF.sub.3 5-Cl Ph H C(O)ME H CH.sub.24-Cl 5-Cl Ph H C(O)ME H CH.sub.24-Br 5-Cl Ph H C(O)Me H CH.sub.24-CF.sub.3 5-Cl Ph H CO.sub.2 Me H CH.sub.24-Cl 5-Cl Ph H CO.sub.2 Me H CH.sub.24-Br 5-Cl Ph H CO.sub.2 Me H CH.sub.24-CF.sub.3 5-Cl Ph H Ph H CH.sub. 24-Cl 5-Cl Ph H Ph H CH.sub.24-Br 5-Cl Ph H Ph H CH.sub.24-CF.sub.3 5-Cl Ph H 4-ClPh H CH.sub.24-Cl 5-Cl Ph H 4-ClPh H CH.sub.24-Br 5-Cl Ph H 4-ClPh H CH.sub.24-CF.sub.3 5-Cl Ph H 4-FPh H CH.sub.24-Cl 5-Cl Ph H 4-FPh H CH.sub.24-Br 5-Cl Ph H 5-FPh H CH.sub.24-CF.sub.3 5-F Ph H Me H CH.sub.24-Cl 5-F Ph H Me H CH.sub.24-Br 5-F Ph H Me H CH.sub.24-CF.sub.3 5-F Ph H Ph H CH.sub.24-Cl 5-F Ph H Ph H CH.sub.24-Br 5-F Ph H Ph H CH.sub.24-CF.sub.3 5-F Ph H SN(Me)CO.sub.2 n-Bu H CH.sub.24-Cl 5-F Ph H SN(Me)CO.sub.2 n-Bu H CH.sub.24-Br 5-F Ph H SN(Me)CO.sub.2 n-Bu H CH.sub.24-CF.sub.3 5-F Ph H SN(i-Pr)CO.sub.2 Et H CH.sub.24-Cl 5-F Ph H SN(i-Pr)CO.sub.2 Et H CH.sub.24-Br 5-F Ph H SN(i-Pr)CO.sub.2 Et H CH.sub.24-CF.sub.3 5-F Ph H SCO.sub.2 n-Hex H CH.sub.24-Cl 5-F Ph H SCO.sub.2 n-Hex H CH.sub.24-Br 5-F Ph H SCO.sub.2 n-Hex H CH.sub.24-CF.sub.3 5-F Ph H SN(Me)SO.sub.2 Me H CH.sub.24-Cl 5-F Ph H SN(Me)SO.sub.2 Me H CH.sub.24-Br 5-F Ph H SN(Me)SO.sub.2 Me H CH.sub.24-CF.sub.3 5-Cl 4-ClPh H Me H CH.sub.24-Cl 5-Cl 4-ClPh H Me H CH.sub.24-Br 5-Cl 4-ClPh H Me H CH.sub.24-CF.sub.3 5-Cl 4-ClPh H 4-FPh H CH.sub.24-Cl 5-Cl 4-ClPh H 4-FPh H CH.sub.24-Br 5-Cl 4-ClPh H 4-FPh H CH.sub.24-CF.sub.3 5-Cl 4-ClPh H SPh H CH.sub.24-Cl 5-Cl 4-ClPh H SPh H CH.sub.24-Br 5-Cl 4-ClPh H SPh H CH.sub.24-CF.sub.3 5-Cl 4-ClPh H CO.sub.2 Et H CH.sub.24-Cl 5-Cl 4-ClPh H CO.sub.2 Et H CH.sub.24-Br 5-Cl 4-ClPh H CO.sub.2 Et H CH.sub.24-CF.sub.3 5-Cl 4-ClPh H SCO.sub.2 n-Bu H CH.sub.24-Cl 5-Cl 4-ClPh H SCO.sub.2 n-Bu H CH.sub.24-Br 5-Cl 4-ClPh H SCO.sub. 2 n-Bu H CH.sub.24-CF.sub.3 5-Cl 4-ClPh H SMe H CH.sub.24-Cl 5-Cl 4-ClPh H SMe H CH.sub.24-Br 5-Cl 4-ClPh H SMe H CH.sub.24-CF.sub.3 5-Cl 4-FPh H CO.sub.2 Me H CH.sub.24-Cl 5-Cl 4-FPh H CO.sub.2 Me H CH.sub.24-Br 5-Cl 4-FPh H CO.sub.2 Me H CH.sub.24-CF.sub.3 5-Cl 4-FPh H SN(Me)SO.sub.2 -4-MePh H CH.sub.24-Cl 5-Cl 4-FPh H SN(Me)SO.sub.2 -4-MePh H CH.sub.24-Br 5-Cl 4-FPh H SN(Me)SO.sub.2 -4-MePh H CH.sub.24-CF.sub.3 5-Cl 4-FPh H SN(Me)P(O)(OEt).sub.2 H CH.sub.24-Cl 5-Cl 4-FPh H SN(Me)P(O)(OEt).sub.2 H CH.sub.24-Br 5-Cl 4-FPh H SN(Me)P(O)(OEt).sub.2 H CH.sub.24-CF.sub.3 5-Cl 4-FPh H ##STR22## H CH.sub.24-Cl 5-Cl 4-FPh H ##STR23## H CH.sub.24-Br 5-Cl 4-FPh H ##STR24## H CH.sub.24-CF.sub.3 5-Cl 4-FPh H CO.sub.2 Et H CH.sub.24-Cl 5-Cl 4-FPh H CO.sub.2 Et H CH.sub.24-Br 5-Cl 4-FPh H CO.sub.2 Et H CH.sub.24-CF.sub.3 5-Cl 4-FPh H Ph H CH.sub.24-Cl 5-Cl 4-FPh H Ph H CH.sub.24-Br 5-Cl 4-FPh H Ph H CH.sub.24-CF.sub.3 5-Cl Ph H H Me CH.sub.24-Cl 5-Cl Ph H H Me CH.sub.24-Br 5-Cl Ph H H Me CH.sub.24-CF.sub.3 5-Cl Ph H H C(O)Me CH.sub.24-Cl 5-Cl Ph H H C(O)Me CH.sub.24-Br 5-Cl Ph H H C(O)Me CH.sub.24-CF.sub.3 5-Cl Ph H. H CO.sub.2 Me CH.sub.24-Cl 5-Cl Ph H H CO.sub.2 Me CH.sub.24-Br 5-Cl Ph H H CO.sub.2 Me CH.sub.24-CF.sub.3 5-Cl Ph H H CO.sub.2 Et CH.sub.24-Cl 5-Cl Ph H H CO.sub.2 Et CH.sub.24-Br 5-Cl Ph H H CO.sub.2 Et CH.sub.24-CF.sub.3 5-Cl Ph H H C(O)Ph CH.sub.24-Cl 5-Cl Ph H H C(O)Ph CH.sub.24-Br 5-Cl Ph H H C(O)Ph CH.sub.24-CF.sub.3 5-Cl Ph H H C(O)nPr CH.sub.24-Cl 5-Cl Ph H H C(O)nPr CH.sub.24-Br 5-Cl Ph H H C(O)nPr CH.sub.24-CF3 5-F Ph H H CH.sub.2 Ph CH24-Cl 5-F Ph H H CH.sub.2 Ph CH24-Br 5-F Ph H H CH.sub.2 Ph CH24-CF.sub.3 5-F Ph H H SN(Me)CO.sub.2 n-dec CH.sub.24-Cl 5-F Ph H H SN(Me)CO.sub.2 n-dec CH.sub.24-Br 5-F Ph H H SN(Me)CO.sub.2 n-dec CH.sub.24-CF.sub.3 5-F Ph H H SN(i-Pr)CO.sub.2 Et CH.sub.24-Cl 5-F Ph H H SN(i-Pr)CO.sub.2 Et CH.sub.24-Br 5-F Ph H H SN(i-Pr)CO.sub.2 Et CH.sub.24-CF.sub.3 5-F Ph H H SCO.sub.2 Et CH.sub.24-Cl 5-F Ph H H SCO.sub.2 Et CH.sub.24-Br 5-F Ph H H SCO.sub.2 Et CH.sub.24-CF.sub.3 5-F Ph H H C(O)Me CH.sub.24-Cl 5-F Ph H H C(O)Me CH.sub.24-Br 5-F Ph H H C(O)Me CH.sub.24-CF.sub.3 5-F Ph H H CO.sub.2 Me CH.sub.24-Cl 5-F Ph H H CO.sub.2 Me CH.sub.24-Br 5-F Ph H H CO.sub.2 Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh H H Me CH.sub.24-Cl 5-Cl 4-ClPh H H Me CH.sub.24-Br 5-Cl 4-ClPh H H Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh H H CO.sub.2 Me CH.sub.24-Cl 5-Cl 4-ClPh H H CO.sub.2 Me CH.sub.24-Br 5-Cl 4-ClPh H H CO.sub.2 Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh H H CO.sub.2 Et CH.sub.24-Cl 5-Cl 4-ClPh H H CO.sub.2 Et CH.sub.24-Br 5-Cl 4-ClPh H H CO.sub.2 Et CH.sub.24-CF.sub.3 5-Cl 4-ClPh H H C(O)Me CH.sub.24-Cl 5-Cl 4-ClPh H H C(O)Me CH.sub.24-Br 5-Cl 4-ClPh H H C(O)Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh H H SN(Et).sub.2 CH.sub.24-Cl 5-Cl 4-ClPh H H SN(Et).sub.2 CH.sub.24-Br 5-Cl 4-ClPh H H SN(Et).sub.2 CH.sub.24-CF.sub.3 5-Cl 4-ClPh H H SO.sub.2 Ph CH.sub.24-Cl 5-Cl 4-ClPh H H SO.sub.2 Ph CH.sub.24-Br 5-Cl 4-ClPh H H SO.sub.2 Ph CH.sub.24-CF.sub.3 5-Cl 4-FPh H H Me CH.sub.24-Cl 5-Cl 4-FPh H H Me CH.sub.24-Br 5-Cl 4-FPh H H Me CH.sub.24-CF.sub.3 5-Cl 4-FPh H H C(O)Me CH.sub.24-Cl 5-Cl 4-FPh H H C(O)Me CH.sub.24-Br 5-Cl 4-FPh H H C(O)Me CH.sub.24-CF.sub.3 5-Cl 4-FPh H H CO.sub.2 Me CH.sub.24-Cl 5-Cl 4-FPh H H CO.sub.2 Me CH.sub.24-Br 5-Cl 4-FPh H H CO.sub.2 Me CH.sub.24-CF.sub.3 5-Cl 4-FPh H H n-Bu CH.sub.24-Cl 5-Cl 4-FPh H H n-Bu CH.sub.24-Br 5-Cl 4-FPh H H n-Bu CH.sub.24-CF.sub.3 5-Cl 4-FPh H H SN(Me)CO.sub.2 Et CH.sub.24-Cl 5-Cl 4-FPh H H SN(Me)CO.sub.2 Et CH.sub.24-Br 5-Cl 4-FPh H H SN(Me)CO.sub.2 Et CH.sub.24-CF.sub.3 5-Cl 4-FPh H H C(O)Ph CH.sub.24-Cl 5-Cl 4-FPh H H C(O)Ph CH.sub.24-Br 5-Cl 4-FPh H H C(O)Ph CH.sub.24-CF.sub.3 5-Cl 4-ClPh Me H Me CH.sub.24-Cl 5-Cl 4-ClPh Me H Me CH.sub.24-Br 5-Cl 4-ClPh Me H Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh Me Me H CH.sub. 24-Cl 5-Cl 4-ClPh Me Me H CH.sub.24-Br 5-Cl 4-ClPh Me Me H CH.sub.24-CF.sub.3 5-Cl 4-ClPh Me Ph H CH.sub.24-Cl 5-Cl 4-ClPh Me Ph H CH.sub.24-Br 5-Cl 4-ClPh Me Ph H CH.sub.24-CF.sub.3 5-Cl 4-ClPh Me H CO.sub.2 Me CH.sub.24-Cl 5-Cl 4-ClPh Me H CO.sub.2 Me CH.sub.24-Br 5-Cl 4-ClPh Me H CO.sub.2 Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh Me H C(O)Me CH.sub.24-Cl 5-Cl 4-ClPh Me H C(O)Me CH.sub.24-Br 5-Cl 4-ClPh Me H C(O)Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh Me H SCO.sub.2 Me CH.sub.24-Cl 5-Cl 4-ClPh Me H SCO.sub.2 Me CH.sub.24-Br 5-Cl 4-ClPh Me H SCO.sub.2 Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh H Me Me CH.sub.24-Cl 5-Cl 4-ClPh H Me Me CH.sub.24-Br 5-Cl 4-ClPh H Me Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh H Me C(O)Me CH.sub.24-Cl 5-Cl 4-ClPh H Me C(O)Me CH.sub.24-Br 5-Cl 4-ClPh H Me C(O)Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh H Ph Me CH.sub.24-Cl 5-Cl 4-ClPh H Ph Me CH.sub.24-Br 5-Cl 4-ClPh H Ph Me CH.sub.24-CF.sub.3 5-Cl 4-ClPh H Ph CO.sub.2 Me CH.sub.24-Cl 5-Cl 4-ClPh H Ph CO.sub.2 Me CH.sub.24-Br 5-Cl 4-ClPh H Ph CO.sub.2 Me CH.sub.24-CF.sub.3 5-Cl Ph H Me Me CH.sub.24-Cl 5-Cl Ph H Me Me CH.sub.24-Br 5-Cl Ph H Me Me CH.sub.24-CF.sub.3 5-Cl Ph H CO.sub.2 Me Me CH.sub.24-Cl 5-Cl Ph H CO.sub.2 Me Me CH.sub.24-Br 5-Cl Ph H CO.sub.2 Me Me CH.sub.2__________________________________________________________________________
TABLE 14______________________________________ ##STR25##R.sub.1 R.sub.2 R.sub.3 R.sub.4 A______________________________________4-CF.sub.3 5-Cl Ph H CH.sub.24-Cl 5-Cl Ph H CH.sub.24-Br 5-Cl Ph H CH.sub.24-OCF.sub.2 H 5-Cl Ph H CH.sub.24-CF.sub.3 5-Cl 4-ClPh H CH.sub.24-Cl 5-Cl 4-ClPh H CH.sub.24-Br 5-Cl 4-ClPh H CH.sub.24-OCF.sub.2 H 5-Cl 4-ClPh H CH.sub.24-CF.sub.3 5-Cl 4-FPh H CH.sub.24-Cl 5-Cl 4-FPh H CH.sub.24-Br 5-Cl 4-FPh H CH.sub.24-OCF.sub.2 H 5-Cl 4-FPh H CH.sub.24-CF.sub.3 5-Cl 4-NO.sub.2 Ph H CH.sub.24-Cl 5-Cl 4-NO.sub.2 Ph H CH.sub.24-Br 5-Cl 4-NO.sub.2 Ph H CH.sub.24-OCF.sub.2 H 5-Cl 4-NO.sub.2 Ph H CH.sub.24-CF.sub.3 5-F Ph H CH.sub.24-Cl 5-F Ph H CH.sub.24-Br 5-F Ph H CH.sub.24-OCF.sub.2 H 5-F Ph H CH.sub.24-CF.sub.3 5-F 4-FPh H CH.sub.24-Cl 5-F 4-FPh H CH.sub.24-Br 5-F 4-FPh H CH.sub.24-OCF.sub.2 H 5-F 4-FPh H CH.sub.24-CF.sub.3 5-F 4-ClPh H CH.sub.24-Cl 5-F 4-ClPh H CH.sub.24-Br 5-F 4-ClPh H CH.sub.24-OCF.sub.2 H 5-F 4-ClPh H CH.sub.24-CF.sub.3 5-F 4-OMePh H CH.sub.24-Cl 5-F 4-OMePh H CH.sub.24-Br 5-F 4-OMePh H CH.sub.24-OCF.sub.2 H 5-F 4-OMePh H CH.sub.24-CF.sub.3 5-Cl Ph Me CH.sub.24-Cl 5-Cl Ph Me CH.sub.24-Br 5-Cl Ph Me CH.sub.24-OCF.sub.2 H 5-Cl Ph Me CH.sub.24-CF.sub.3 5-Cl 5-Cl Me CH.sub.24-Cl 5-Cl 5-Cl Me CH.sub.24-Br 5-Cl 5-Cl Me CH.sub.24-OCF.sub.2 H 5-Cl 5-Cl Me CH.sub.24-CF.sub.3 5-F Ph Me CH.sub.24-Cl 5-F Ph Me CH.sub.24-Br 5-F Ph Me CH.sub.24-OCF.sub.2 H 5-F Ph Me CH.sub.24-CF.sub.3 5-F 5-Cl Me CH.sub.24-Cl 5-F 5-Cl Me CH.sub.24-Br 5-F 5-Cl Me CH.sub.24-OCF.sub.2 H 5-F 5-Cl Me CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me H CH.sub.24-Cl 5-Cl CO.sub.2 Me H CH.sub.24-Br 5-Cl CO.sub.2 Me H CH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me H CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me Me CH.sub.24-Cl 5-Cl CO.sub.2 Me Me CH.sub.24-Br 5-Cl CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me Me CH.sub.24-CF.sub.3 4-F CO.sub.2 Me H CH.sub.24-Cl 4-F CO.sub.2 Me H CH.sub.24-Br 4-F CO.sub.2 Me H CH.sub.24-OCF.sub.2 H 4-F CO.sub.2 Me H CH.sub.24-CF.sub.3 4-F CO.sub.2 Me Me CH.sub.24-Cl 4-F CO.sub.2 Me Me CH.sub.24-Br 4-F CO.sub.2 Me Me CH.sub.24-OCF.sub.2 H 4-F CO.sub.2 Me Me CH.sub.24-OCF.sub.3 5-Cl 4-ClPh H CH.sub.24-OCF.sub.2 CF.sub.2 H 5-Cl 4-ClPh H CH.sub.23-Cl,4-CF.sub.3 5-Cl 4-ClPh H CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl 4-ClPh H CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl 4-ClPh H CH.sub.24-CN 5-Cl 4-ClPh H CH.sub.24-NO.sub.2 5-Cl 4-ClPh H CH.sub.24-F 5-Cl 4-ClPh H CH.sub.23,4-di-Cl 5-Cl 4-ClPh H CH.sub.24-CO.sub.2 Me 5-Cl 4-ClPh H CH.sub.24-SCF.sub.2 H 5-Cl 4-ClPh H CH.sub.24-SCF.sub.2 CF.sub.2 H 5-Cl 4-ClPh H CH.sub.24-OCF.sub.2 CF.sub.2 H 5-Cl 4-ClPh H CH.sub.24-OCF.sub.3 5-Cl Ph H CH.sub.24-OCF.sub.2 CF.sub.2 H 5-Cl Ph H CH.sub.23-Cl,4-CF.sub.3 5-Cl Ph H CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl Ph H CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl Ph H CH.sub.24-CN 5-Cl Ph H CH.sub.24-NO.sub.2 5-Cl Ph H CH.sub.24-F 5-Cl Ph H CH.sub.23,4-di-Cl 5-Cl Ph H CH.sub.24-CO.sub.2 Me 5-Cl Ph H CH.sub.24-SCF.sub.2 H 5-Cl Ph H CH.sub.24-SCF.sub.2 CF.sub.2 H 5-Cl Ph H CH.sub.24-OCH.sub.2 CF.sub. 3 5-Cl Ph H CH.sub.24-CF.sub.3 5-Cl Ph Me O4-Cl 5-Cl Ph Me O4-Br 5-Cl Ph Me O4-OCF.sub.2 H 5-Cl Ph Me O4-CF.sub.3 5-Cl 4-ClPh Me O4-Cl 5-Cl 4-ClPh Me O4-Br 5-Cl 4-ClPh Me O4-OCF.sub.2 H 5-Cl 4-ClPh Me O4-CF.sub.3 5-F Ph Me O4-Cl 5-F Ph Me O4-Br 5-F Ph Me O4-OCF.sub.2 H 5-F Ph Me O4-CF.sub.3 5-F 4-ClPh Me O4-Cl 5-F 4-ClPh Me O4-Br 5-F 4-ClPh Me O4-OCF.sub.2 H 5-F 4-ClPh Me O4-CF.sub.3 5-F Me allyl O4-OCF.sub.3 5-F Me allyl O4-CF.sub.3 5-Cl Me allyl O4-OCF.sub.3 5-Cl Me allyl O4-CF.sub.3 5-CF.sub.3 Me allyl O4-OCF.sub.3 5-CF.sub.3 Me allyl O4-CF.sub.3 5-F CH.sub.2 Ph Me O4-OCF.sub.3 5-F CH.sub.2 Ph Me O4-CF.sub.3 5-Cl CH.sub.2 Ph Me O4-OCF.sub.3 5-Cl CH.sub.2 Ph Me O4-CF.sub.3 5-F Me H O4-OCF.sub.3 5-F Me H O4-CF.sub.3 5-Cl Me H O4-OCF.sub.3 5-Cl Me H O4-CF.sub.3 5-F i-Pr H O4-OCF.sub.3 5-F i-Pr H O4-CF.sub.3 5-Cl i-Pr H O4-OCF.sub.3 5-Cl i-Pr H O4-CF.sub.3 5-Cl Ph H CH.sub.2 CH.sub.24-Cl 5-Cl Ph H CH.sub.2 CH.sub.24-Br 5-Cl Ph H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl Ph H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-Cl 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-Br 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl 4-FPh H CH.sub.2 CH.sub.24-Cl 5-Cl 4-FPh H CH.sub.2 CH.sub.24-Br 5-Cl 4-FPh H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl 4-FPh H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl 4-NO.sub.2 Ph H CH.sub.2 CH.sub.24-Cl 5-Cl 4-NO.sub.2 Ph H CH.sub.2 CH.sub.24-Br 5-Cl 4-NO.sub.2 Ph H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl 4-NO.sub.2 Ph H CH.sub.2 CH.sub.24-CF.sub.3 5-F Ph H CH.sub.2 CH.sub.24-Cl 5-F Ph H CH.sub.2 CH.sub.24-Br 5-F Ph H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F Ph H CH.sub.2 CH.sub.24-CF3 5-F 4-FPh H CH.sub.2 CH.sub.24-Cl 5-F 4-FPh H CH.sub.2 CH.sub.24-Br 5-F 4-FPh H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F 4-FPh H CH.sub.2 CH.sub.24-CF.sub.3 5-F 4-ClPh H CH.sub.2 CH.sub.24-Cl 5-F 4-ClPh H CH.sub.2 CH.sub.24-Br 5-F 4-ClPh H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F 4-ClPh H CH.sub.2 CH.sub.24-CF.sub.3 5-F 4-OMe H CH.sub.2 CH.sub.24-Cl 5-F 4-OMe H CH.sub.2 CH.sub.24-Br 5-F 4-OMe H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F 4-OMe H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl Ph Me CH.sub.2 CH.sub.24-Cl 5-Cl Ph Me CH.sub.2 CH.sub.24-Br 5-Cl Ph Me CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl Ph Me CH.sub.2 CH.sub.24-CF.sub.3 5-Cl 4-ClPh Me CH.sub.2 CH.sub.24-Cl 5-Cl 4-ClPh Me CH.sub.2 CH.sub.24-Br 5-Cl 4-ClPh Me CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl 4-ClPh Me CH.sub.2 CH.sub. 24-CF.sub.3 5-F Ph Me CH.sub.2 CH.sub.24-Cl 5-F Ph Me CH.sub.2 CH.sub.24-Br 5-F Ph Me CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F Ph Me CH.sub.2 CH.sub.24-CF.sub.3 5-F 4-ClPh Me CH.sub.2 CH.sub.24-Cl 5-F 4-ClPh Me CH.sub.2 CH.sub.24-Br 5-F 4-ClPh Me CH.sub.2 CH.sub.24-OCF.sub.2 H 5-F 4-ClPh Me CH.sub.2 CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-Cl 5-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-Br 5-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me H CH.sub.2 CH.sub.24-CF.sub.3 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.24-Cl 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.24-Br 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.24-OCF.sub.2 H 5-Cl CO.sub.2 Me Me CH.sub.2 CH.sub.24-CF.sub.3 4-F CO.sub.2 Me H CH.sub.2 CH.sub.24-Cl 4-F CO.sub.2 Me H CH.sub.2 CH.sub.24-Br 4-F CO.sub.2 Me H CH.sub.2 CH.sub.24-OCF.sub.2 H 4-F CO.sub.2 Me H CH.sub.2 CH.sub.24-OCF.sub.3 4-F CO.sub.2 Me Me CH.sub.2 CH.sub.24-Cl 4-F CO.sub.2 Me Me CH.sub.2 CH.sub.24-Br 4-F CO.sub.2 Me Me CH.sub.2 CH.sub.24-OCF.sub.2 H 4-F CO.sub.2 Me Me CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-OCF.sub.2 CF.sub.2 H 5-Cl 4-ClPh H CH.sub.2 CH.sub.23-Cl,4-CF.sub.3 5-Cl 4-ClPh H CH.sub.2 CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl 4-ClPh H CH.sub.2 CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-CN 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-NO.sub.2 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-F 5-Cl 4-ClPh H CH.sub.2 CH.sub.23,4-di-Cl 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-CO.sub.2 Me 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-SCF.sub.2 H 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-SCF.sub.2 CF.sub.2 H 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-OCH.sub.2 CF.sub.3 5-Cl 4-ClPh H CH.sub.2 CH.sub.24-OCF.sub.3 5-Cl Ph H CH.sub.2 CH.sub.24-OCF.sub. 2 CF.sub.2 H 5-Cl Ph H CH.sub.2 CH.sub.23-Cl,4-CF.sub.3 5-Cl Ph H CH.sub.2 CH.sub.23,4-CH.sub.2 C(Me).sub.2 O 5-Cl Ph H CH.sub.2 CH.sub.23,4-CF.sub.2 CF.sub.2 O 5-Cl Ph H CH.sub.2 CH.sub.24-CN 5-Cl Ph H CH.sub.2 CH.sub.24-NO.sub.2 5-Cl Ph H CH.sub.2 CH.sub.24-F 5-Cl Ph H CH.sub.2 CH.sub.23,4-di-Cl 5-Cl Ph H CH.sub.2 CH.sub.24-CO.sub.2 Me 5-Cl Ph H CH.sub.2 CH.sub.24-SCF.sub.2 H 5-Cl Ph H CH.sub.2 CH.sub.24-SCF.sub.2 CF.sub.2 H 5-Cl Ph H CH.sub.2 CH.sub.24-OCH.sub.2 CF.sub.3 5-Cl Ph H CH.sub.2 CH.sub.2______________________________________
TABLE 15______________________________________ ##STR26##Q R.sub.1 R.sub.2 R.sub.3 R.sub.4 A______________________________________Q-2 CF.sub.3 H H H CH.sub.2Q-2 OCF.sub.3 H H H CH.sub.2Q-2 CF.sub.3 H Me H CH.sub.2Q-2 OCF.sub.3 H Me H CH.sub.2Q-2 CF.sub.3 H 4-FPh H CH.sub.2Q-2 OCF.sub.3 H 4-FPh H CH.sub.2Q-2 CF.sub.3 H 4-ClPh H CH.sub.2Q-2 OCF.sub.3 H 4-ClPh H CH.sub.2Q-2 CF.sub.3 5-CF.sub.3 Me H CH.sub.2Q-2 OCF.sub.3 5-CF.sub.3 Me H CH.sub.2Q-2 CF.sub.3 5-CF.sub.3 4-FPh H CH.sub.2Q-2 OCF.sub.3 5-CF.sub.3 4-FPh H CH.sub.2Q-2 CF.sub.3 5-CF.sub.3 4-ClPh H CH.sub.2Q-2 OCF.sub.3 5-CF.sub.3 4-ClPh H CH.sub.2Q-2 CF.sub.3 5-Cl Me H CH.sub.2Q-2 OCF.sub.3 5-Cl Me H CH.sub.2Q-2 CF.sub.3 5-Cl 4-FPh H CH.sub.2Q-2 OCF.sub.3 5-Cl 4-FPh H CH.sub.2Q-2 CF.sub.3 H H H OQ-2 OCF.sub.3 H H H OQ-2 CF.sub.3 H Me H OQ-2 OCF.sub.3 H Me H OQ-2 CF.sub.3 H 4-FPh Me OQ-2 OCF.sub.3 H 4-FPh Me OQ-2 CF.sub.3 H 4-ClPh Me OQ-2 OCF.sub.3 H 4-ClPh Me OQ-2 CF.sub.3 H i-Pr H OQ-2 OCF.sub.3 H i-Pr H OQ-2 CF.sub.3 5-CF.sub.3 H H OQ-2 OCF.sub.3 5-CF.sub.3 H H OQ-2 CF.sub.3 5-CF.sub.3 Me H OQ-2 OCF.sub.3 5-CF.sub.3 Me H OQ-2 CF.sub.3 5-CF.sub.3 i-Pr H OQ-2 OCF.sub.3 5-CF.sub.3 i-Pr H OQ-2 CF.sub.3 5-CF.sub.3 4-FPh Me OQ-2 OCF.sub.3 5-CF.sub.3 4-FPh Me OQ-3 CF.sub.3 H H H CH.sub.2Q-3 OCF.sub.3 H H H CH.sub.2Q-3 CF.sub.3 H Me H CH.sub.2Q-3 OCF.sub.3 H Me H CH.sub.2Q-3 CF.sub.3 H 4-FPh H CHQ-3 OCF.sub.3 H 4-FPh H CH.sub.2Q-3 CF.sub.3 H 4-ClPh H CH.sub.2Q-3 OCF.sub.3 H 4-ClPh H CH.sub.2Q-3 CF.sub.3 4-CF.sub.3 Me H CH.sub.2Q-3 OCF.sub.3 4-CF.sub.3 Me H CH.sub.2Q-3 CF.sub.3 4-CF.sub.3 4-FPh H CH.sub.2Q-3 OCF.sub.3 4-CF.sub.3 4-FPh H CH.sub.2Q-3 CF.sub.3 4-CF.sub.3 4-ClPh H CH.sub.2Q-3 OCF.sub.3 4-CF.sub.3 4-ClPh H CH.sub.2Q-3 CF.sub.3 4-CF.sub.3 Me H CH.sub.2Q-3 OCF.sub.3 4-CF.sub.3 Me H CH.sub.2Q-3 CF.sub.3 4-CF.sub.3 4-FPh H CH.sub.2Q-3 OCF.sub.3 4-CF.sub.3 4-FPh H CH.sub.2Q-3 CF.sub.3 H H H OQ-3 OCF.sub.3 H H H OQ-3 CF.sub.3 H Me H OQ-3 OCF.sub.3 H Me H OQ-3 CF.sub.3 H 4-FPh Me OQ-3 OCF.sub.3 H 4-FPh Me OQ-3 CF.sub.3 H 4-ClPh Me OQ-3 OCF.sub.3 H 4-ClPh Me OQ-3 CF.sub.3 H i-Pr H OQ-3 OCF.sub.3 H i-Pr H OQ-3 CF.sub.3 4-CF.sub.3 H H OQ-3 OCF.sub.3 4-CF.sub.3 H H OQ-3 CF.sub.3 4-CF.sub.3 Me H OQ-3 OCF.sub.3 4-CF.sub.3 Me H OQ-3 CF.sub.3 4-CF.sub.3 i-Pr H OQ-3 OCF.sub.3 4-CF.sub.3 i-Pr H OQ-3 CF.sub.3 4-CF.sub.3 4-FPh Me OQ-3 OCF.sub.3 4-CF.sub.3 4-FPh Me OQ-4 CF.sub.3 H H H CH.sub.2Q-4 OCF.sub.3 H H H CH.sub.2Q-4 CF.sub.3 H Me H CH.sub.2Q-4 OCF.sub.3 H Me H CH.sub.2Q-4 CF.sub.3 H 4-FPh H CH.sub.2Q-4 OCF.sub.3 H 4-FPh H CH.sub.2Q-4 CF.sub.3 H 4-ClPh H CH.sub.2Q-4 OCF.sub.3 H 4-ClPh H CH.sub.2Q-4 CF.sub.3 5-CF.sub.3 Me H CH.sub.2Q-4 OCF.sub.3 5-CF.sub.3 Me H CH.sub.2Q-4 CF.sub.3 5-CF.sub.3 4-FPh H CH.sub.2Q-4 OCF.sub.3 5-CF.sub.3 4-FPh H CH.sub.2Q-4 CF.sub.3 5-CF.sub.3 4-ClPh H CH.sub.2Q-4 OCF.sub.3 5-CF.sub.3 4-ClPh H CH.sub.2Q-4 CF.sub.3 4-F Me H CH.sub.2Q-4 OCF.sub.3 4-F Me H CH.sub.2Q-4 CF.sub.3 4-F 4-FPh H CH.sub.2Q-4 OCF.sub.3 4-F 4-FPh H CH.sub.2Q-4 CF.sub.3 H H H OQ-4 OCF.sub.3 H H H OQ-4 CF.sub.3 H Me H OQ-4 OCF.sub.3 H Me H OQ-4 CF.sub.3 H 4-FPh Me OQ-4 OCF.sub.3 H 4-FPh Me OQ-4 CF.sub.3 H 4-ClPh Me OQ-4 OCF.sub.3 H 4-ClPh Me OQ-4 CF.sub.3 H i-Pr H OQ-4 OCF.sub.3 H i-Pr H OQ-4 CF.sub.3 5-CF.sub.3 H H OQ-4 OCF.sub.3 5-CF.sub.3 H H OQ-4 CF.sub.3 5-CF.sub.3 Me H OQ-4 OCF.sub.3 5-CF.sub.3 Me H OQ-4 CF.sub.3 5-CF.sub.3 i-Pr H OQ-4 OCF.sub.3 5-CF.sub.3 i-Pr H OQ-4 CF.sub.3 5-CF.sub.3 4-FPh Me OQ-4 OCF.sub.3 5-CF.sub.3 4-FPh Me OQ-5 CF.sub.3 H H H CH.sub.2Q-5 OCF.sub.3 H H H CH.sub.2Q-5 CF.sub.3 H Me H CH.sub.2Q-5 OCF.sub.3 H Me H CH.sub.2Q-5 CF.sub.3 H 4-FPh H CH.sub.2Q-5 OCF.sub.3 H 4-FPh H CH.sub.2Q-5 CF.sub.3 H 4-ClPh H CH.sub.2Q-5 OCF.sub.3 H 4-ClPh H CH.sub.2Q-5 CF.sub.3 5-CF.sub.3 Me H CH.sub.2Q-5 OCF.sub.3 5-CF.sub.3 Me H CH.sub.2Q-5 CF.sub.3 5-CF.sub.3 4-FPh H CH.sub.2Q-5 OCF.sub.3 5-CF.sub.3 4-FPh H CH.sub.2Q-5 CF.sub.3 5-CF.sub.3 4-ClPh H CH.sub.2Q-5 OCF.sub.3 5-CF.sub.3 4-ClPh H CH.sub.2Q-5 CF.sub.3 4-F Me H CH.sub.2Q-5 OCF.sub.3 4-F Me H CH.sub.2Q-5 CF.sub.3 4-F 4-FPh H CH.sub.2Q-5 OCF.sub.3 4-F 4-FPh H CH.sub.2Q-5 CF.sub.3 5-CF.sub.3 H H OQ-5 OCF.sub.3 5-CF.sub.3 H H OQ-5 CF.sub.3 5-CF.sub.3 Me H OQ-5 OCF.sub.3 5-CF.sub.3 Me H OQ-5 CF.sub.3 5-CF.sub.3 4-FPh Me OQ-5 OCF.sub.3 5-CF.sub.3 4-.sub.3 FPh Me OQ-5 CF.sub.3 5-CF.sub.3 4-ClPh Me OQ-5 OCF.sub.3 5-CF.sub.3 4-ClPh Me OQ-5 CF.sub. 3 5-CF.sub.3 i-Pr H OQ-5 OCF.sub.3 5-CF.sub.3 i-Pr H OQ-5 CF.sub.3 5-Cl H H OQ-5 OCF.sub.3 5-Cl H H OQ-5 CF.sub.3 5-Cl Me H OQ-5 OCF.sub.3 5-Cl Me H OQ-5 CF.sub.3 5-Cl i-Pr H OQ-5 OCF.sub.3 5-Cl i-Pr H OQ-5 CF.sub.3 5-Cl 4-FPh Me OQ-5 OCF.sub.3 5-Cl 4-FPh Me O______________________________________
TABLE 16______________________________________ ##STR27##Q R.sub.1 R.sub.2 R.sub.3 R.sub.4 A______________________________________Q-6 CF.sub.3 H H H CH.sub.2Q-6 OCF.sub.3 H H H CH.sub.2Q-6 CF.sub.3 H Me H CH.sub.2Q-6 OCF.sub.3 H Me H CH.sub.2Q-6 CF.sub.3 H 4-FPh H CH.sub.2Q-6 OCF.sub.3 H 4-FPh H CH.sub.2Q-6 CF.sub.3 H 4-ClPh H CH.sub.2Q-6 OCF.sub.3 H 4-ClPh H CH.sub.2Q-6 CF.sub.3 5-Cl Me H CH.sub.2Q-6 OCF.sub.3 5-Cl Me H CH.sub.2Q-6 CF.sub.3 5-Cl 4-FPh H CH.sub.2Q-6 OCF.sub.3 5-Cl 4-FPh H CH.sub.2Q-6 CF.sub.3 5-Cl 4-ClPh H CH.sub.2Q-6 OCF.sub.3 5-Cl 4-ClPh H CH.sub.2Q-6 CF.sub.3 5-F Me H CH.sub.2Q-6 OCF.sub.3 5-F Me H CH.sub.2Q-6 CF.sub.3 5-F 4-FPh H CH.sub.2Q-6 OCF.sub.3 5-F 4-F Ph H CH.sub.2Q-6 CF.sub.3 H H H OQ-6 OCF.sub.3 H H H OQ-6 CF.sub.3 H Me H OQ-6 OCF.sub.3 H Me H OQ-6 CF.sub.3 H 4-FPh Me OQ-6 OCF.sub.3 H 4-.sub.3 FPh Me OQ-6 CF.sub.3 H 4-ClPh Me OQ-6 OCF.sub.3 H 4-ClPh Me OQ-6 CF.sub.3 H i-Pr H OQ-6 OCF.sub.3 H i-Pr H OQ-6 CF.sub.3 5-Cl H H OQ-6 OCF.sub.3 5-Cl H H OQ-6 CF.sub.3 5-Cl Me H OQ-6 OCF.sub.3 5-Cl Me H OQ-6 CF.sub.3 5-Cl i-Pr H OQ-6 OCF.sub.3 5-Cl i-Pr H OQ-6 CF.sub.3 5-Cl 4-FPh Me OQ-6 OCF.sub.3 5-Cl 4-FPh Me OQ-7 CF.sub.3 H H H CH.sub.2Q-7 OCF.sub.3 H H H CH.sub.2Q-7 CF.sub.3 H Me H CH.sub.2Q-7 OCF.sub.3 H Me H CH.sub.2Q-7 CF.sub.3 H 4-FPh H CH.sub.2Q-7 OCF.sub.3 H 4-FPh H CH.sub.2Q-7 CF.sub.3 H 4-ClPh H CH.sub.2Q-7 OCF.sub.3 H 4-ClPh H CH.sub.2Q-7 CF.sub.3 4-Cl Me H CH.sub.2Q-7 OCF.sub.3 4-Cl Me H CH.sub.2Q-7 CF.sub.3 4-Cl 4-FPh H CH.sub.2Q-7 OCF.sub.3 4-Cl 4-FPh H CH.sub.2Q-7 CF.sub.3 4-Cl 4-ClPh H CH.sub.2Q-7 OCF.sub.3 4-Cl 4-ClPh H CH.sub.2Q-7 CF.sub.3 4-F Me H CH.sub.2Q-7 OCF.sub.3 4-F Me H CH.sub.2Q-7 CF.sub.3 4-F 4-FPh H CH.sub.2Q-7 OCF.sub.3 4-F 4-FPh H CH.sub.2Q-7 CF.sub.3 H H H OQ-7 OCF.sub.3 H H H OQ-7 CF.sub.3 H Me H OQ-7 OCF.sub.3 H Me H OQ-7 CF.sub.3 H 4-FPh Me OQ-7 OCF.sub.3 H 4-.sub.3 FPh Me OQ-7 CF.sub.3 H 4-ClPh Me OQ-7 OCF.sub.3 H 4-ClPh Me OQ-7 CF.sub.3 H i-Pr H OQ-7 OCF.sub.3 H i-Pr H OQ-7 CF.sub.3 4-F H H OQ-7 OCF.sub.3 4-F H H OQ-7 CF.sub.3 4-F Me H OQ-7 OCF.sub.3 4-F Me H OQ-7 CF.sub.3 4-F i-Pr H OQ-7 OCF.sub.3 4-F i-Pr H OQ-7 CF.sub.3 4-F 4-FPh Me OQ-7 OCF.sub.3 4-F 4-FPh Me OQ-8 CF.sub.3 H H H CH.sub.2Q-8 OCF.sub.3 H H H CH.sub.2Q-8 CF.sub.3 H Me H CH.sub.2Q-8 OCF.sub.3 H Me H CH.sub.2Q-8 CF.sub.3 H 4-FPh H CH.sub.2Q-8 OCF.sub.3 H 4-FPh H CH.sub.2Q-8 CF.sub.3 H 4-ClPh H CH.sub.2Q-8 OCF.sub.3 H 4-ClPh H CH.sub.2Q-8 CF.sub.3 4-F Me H CH.sub.2Q-8 OCF.sub.3 4-F Me H CH.sub.2Q-8 CF.sub.3 4-F 4-FPh H CH.sub.2Q-8 OCF.sub.3 4-F 4-FPh H CH.sub.2Q-8 CF.sub.3 4-F 4-ClPh H CH.sub.2Q-8 OCF.sub.3 4-F 4-ClPh H CH.sub.2Q-8 CF.sub.3 5-Cl Me H CH.sub.2Q-8 OCF.sub.3 5-Cl Me H CH.sub.2Q-8 CF.sub.3 5-Cl 4-FPh H CH.sub.2Q-8 OCF.sub.3 5-Cl 4-FPh H CH.sub.2Q-8 CF.sub.3 4-F H H OQ-8 OCF.sub.3 4-F H H OQ-8 CF.sub.3 4-F Me H OQ-8 OCF.sub.3 4-F Me H OQ-8 CF.sub.3 4-F 4-FPh Me OQ-8 OCF.sub.3 4-F 4-.sub.3 FPh Me OQ-8 CF.sub.3 4-F 4-ClPh Me OQ-8 OCF.sub.3 4-F 4-ClPh Me OQ-8 CF.sub.3 4-F i-Pr H OQ-8 OCF.sub.3 4-F i-Pr H OQ-8 CF.sub.3 5-Cl H H OQ-8 OCF.sub.3 5-Cl H H OQ-8 CF.sub.3 5-Cl Me H OQ-8 OCF.sub.3 5-Cl Me H OQ-8 CF.sub.3 5-Cl i-Pr H OQ-8 OCF.sub.3 5-Cl i-Pr H OQ-8 CF.sub.3 5-Cl 4-FPh Me OQ-8 OCF.sub.3 5-Cl 4-FPh Me O______________________________________
Arthropodicidal Formulation and Use
The compounds of this invention will generally be used in formulation with a carrier comprising a liquid or solid diluent or an organic solvent. Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, baits, wettable powders, emulsifiable concentrates, dry flowables and the like. Many of these can be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of a) about 0.1% to 20% surfactant(s) and b) about 5% to 99% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
______________________________________ Percent by Weight Active Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 25-90 0-74 1-10Oil Suspensions, 1-50 40-95 0-35Emulsions, Solutions,(including EmulsifiableConcentrates)Dusts 1-25 70-99 0-5Granules, Baits 0.01-95 5-99 0-15and PelletsHigh Strength 90-99 0-10 0-2Compositions______________________________________
Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for wettable 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", Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and wood, "Encyclopedia of Surface Active Agents", Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection Agency for the use intended.
The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, U.S. Pat. No. 3,060,084). Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pages 147 and following, and "Perry's Chemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York, 1963, pages 8 to 59 and following.
EXAMPLE A
Emulsifiable Concentrate
______________________________________2-(5-chloro-2,3-dihydro-2-phenyl-1H-inden-1-ylidene)- 20%N-[4-(trifluoromethyl)phenyl]hydrazinecarbox-amideblend of oil soluble sulfonates 10%and polyoxyethylene ethersisophorone 70%______________________________________
The ingredients are combined and stirred with gentle warming to speed solution. A fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product.
EXAMPLE B
Wettable Powder
______________________________________2-(5-chloro-2,3-dihydro-2-phenyl-1H-inden-1-ylidene)- 30%N-[4-(trifluoromethyl)phenyl]hydrazinecarbox-amidesodium alkylnaphthalenesulfonate 2%sodium ligninsulfonate 2%synthetic amorphous silica 3%kaolinite 63%______________________________________
The active ingredient is mixed with the inert materials in a blender. After grinding in a hammermill, the material is re-blended and sifted through 50 mesh screen.
EXAMPLE C
Dust
______________________________________Wettable powder of Example B 10%pyrophyllite (powder) 90%______________________________________
The wettable powder and the pyrophyllite diluent are thoroughly blended and then packaged. The product is suitable for use as a dust.
EXAMPLE D
Granule
______________________________________2-[5-chloro-2-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-y 10%lidene]-N-[4-(trifluoromethyl)phenyl]hydrazine-carboxamideattapulgite granules (low volative 90%matter, 0.71/0.30 mm; U.S.S. No.25-50 sieves)______________________________________
The active ingredient is dissolved in a volatile solvent such as acetone and sprayed upon dedusted and pre-warmed attapulgite granules in a double cone blender. The acetone is then driven off by heating. The granules are then allowed to cool and are packaged.
EXAMPLE E
Granule
______________________________________Wettable powder of Example B 15%gypsum 69%potassium sulfate 16%______________________________________
The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 0.1 to 0.42 mm (U.S.S. No. 18 to 40 sieves), the granules are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain 4.5% active ingredient.
EXAMPLE F
Solution
______________________________________2-(5-chloro-2,3-dihydro-2-phenyl-1H-inden-1-ylidene)- 25%N-[4-(trifluoromethyl)phenyl]hydrazinecarbox-amideN-methyl-pyrrolidone 75%______________________________________
The ingredients are combined and stirred to produce a solution suitable for direct, low volume application.
EXAMPLE G
Aqueous Suspension
______________________________________2-(5-chloro-2,3-dihydro-2-phenyl-1H-inden-1-ylidene)- 40%N-[4-(trifluoromethyl)phenyl]hydrazinecarbox-amidepolyacrylic acid thickener 0.3%dodecyclophenol polyethylene glycol 0.5%etherdisodium phosphate 1.0%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 H
Oil Suspension
______________________________________2-[5-chloro-2-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-y 35.0%lidene]-N-[4-(trifluoromethyl]phenyl]hydrazine-carboxamideblend of polyalcohol carboxylic 6.0%esters and oil soluble petroleumsulfonatesxylene range solvent 59.0%______________________________________
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 I
Bait Granules
______________________________________2-(5-chloro-2,3-dihydro-2-phenyl-1H-inden-1-ylidene)- 3.0%N-[4-(trifluoromethyl)phenyl]hydrazinecarbox-amideblend of polyethoxylated nonyl- 9.0%phenols and sodium dodecyl-benzene sulfonatesground up corn cobs 88.0%______________________________________
The active ingredient and surfactant blend are dissolved in a suitable solvent such as acetone and sprayed onto the ground corn cobs. The granules are then dried and packaged. Compounds of Formula I can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of effective agricultural protection. Examples of other agricultural protectants with which compounds of the present invention can be mixed or formulated are:
Insecticides
3-hydroxy-N-methylcrotonamide (dimethylphosphate) ester (monocrotophos)
methylcarbamic acid, ester with 2,3-dihydro-2,2-dimethyl-7-benzofuranol (carbofuran)
O-[2,4,5-trichloro-.alpha.-(chloromethyl)benzyl]phosphoric acid, O',O'-dimethyl ester (tetrachlorvinphos)
2-mercaptosuccinic acid, diethyl ester, S-ester with thionophosphoric acid, dimethyl ester (malathion)
phosphorothioic acid, O,O-dimethyl, O-p-nitrophenyl ester (methyl parathion)
methylcarbamic acid, ester with .alpha.-naphthol (carbaryl)
methyl O-(methylcarbamoyl)thiolacetohydroxamate (methomyl)
N'-(4- chloro-o-tolyl)-N,N-dimethylformamidine (chlordimeform)
O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidylphosphorothioate (diazinon)
octachlorocamphene (toxaphene)
O-ethyl O-p-nitrophenyl phenylphosphonothioate (EPN)
(S)-a-cyano-m-phenoxybenzyl(1R,3R)-3-(2,2-dibromovinyl) -2 ,2-dimethylcyclopropanecarboxylate (deltamethrin)
Methyl-N',N'-dimethyl -N-[(methylcarbamoyl)oxy]-1-thioox amimidate (oxamyl)
cyano(3-phenoxyphenyl) -methyl-4-chloro-a-(1-methylethyl)benzeneacetate (fenvalerate)
(3-phenoxyphenyl)methyl(+)-cis,trans-3-(2,2-dichloro ethenyl)-2,2-dimethylcyclopropanecarboxylate (permethrin)
a-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl) -2,2-dimethylcyclopropane carboxylate (cypermethrin)
O-ethyl-S-(p-chlorophenyl) ethylphosphonodithioate (profenofos)
phosphorothiolothionic acid,
O-ethyl-O-[4-(methylthio)-phenyl]-S-n-propyl ester (sulprofos).
Additional insecticides are listed hereafter by their common names: triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos, dimethoate, fonophos, isofenphos, methidathion, methamidiphos, monocrotphos, phosmet, phosphamidon, phosalone, pirimicarb, phorate, profenofos, terbufos, trichlorfon, methoxychlor, bifenthrin, biphenate, cyfluthrin, fenpropathrin, fluvalinate, flucythrinate, tralomethrin, metaldehyde and rotenone.
Fungicides
methyl 2-benzimidazolecarbamate (carbendazim)
tetramethylthiuram disulfide (thiuram)
n-dodecylguanidine acetate (dodine)
manganese ethylenebisdithiocarbamate (maneb)
1,4-dichloro-2,5-dimethoxybenzene (chloroneb)
methyl 1-(butylcarbamoly)-2-benzimidazolecarbamate (benomyl)
1-[2-(2,4-dichlorophenyl)-4-propyl-l,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (propiconazole)
2-cyano-N-ethylcarbamoy-2-methoxyiminoacetamide (cymoxanil)
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone (triadimefon)
N-(trichloromethylthio)tetrahydrophthalimide (captan)
N-(trichloromethylthio)phthalimide (folpet)
1-[[[bis(4-fluorophenyl)][methyl]silyl]methyl]-1H-1,2,4-triazole.
Nematocides
S-methyl 1-(dimethylcarbamoyl)-N-(methylcarbamoyloxy)thioformimidate
S-methyl
1-carbamoyl-N-(methylcarbamoyloxy)thioformimidate
N-isopropylphosphoramidic acid, O-ethyl
O'-[4-(methylthio)-m-tolyl]diester (fenamiphos)
Bactericides
tribasic copper sulfate
streptomycin sulfate
Acaricides
senecioic acid, ester with 2-sec-butyl-4,6-dinitrophenol (binapacryl)
6-methyl-1,3-cithiolo[4,5-.beta.]quinoxalin-2-one (oxythioquinox)
ethyl 4,4'-dichlorobenzilate (chlorobenzilate)
1,1-bis([-chlorophenyl)-2,2,2-trichloroethanol (dicofol)
bis(pentachloro-2,4-cyclopentadien-1-yl) (dienochlor)
tricyclohexyltin hydroxide (cyhexatin)
trans-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxothiazolidine-3-carboxamide (hexythiazox)
amitraz
propargite
fenbutatin-oxide
Biological
Bacillus thuringiensis
Avermectin B.
Utility
The compounds of this invention exhibit activity against a wide spectrum of foliar and soil inhabiting arthropods which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will recognize that not all compounds are equally effective against all pests but the compounds of this invention display activity against economically important agronomic, forestry, greenhouse, ornamental food and fiber product, stored product, and nursery pests, such as:
larvae of the order Lepidoptera including fall and beet armyworm and other Spodoptera spp., tobacco budworm, corn earworm and other Heliothis spp., European corn borer, navel orangeworm, stalk/stem borers and other pyralids, cabbage and soybean loopers and other loopers, codling moth, grape berry moth and other tortricids, black cutworm, spotted cutworm, other cutworms and other noctuids, diamondback moth, green cloverworm, velvetbean caterpillar, green cloverworm, pink bollworm, gypsy moth, and spruce budworm;
foliar feeding larvae and adults of the order Coleoptera including Colorado potato beetle, Mexican bean beetle, flea beetle, Japanese beetles, and other leaf beetles, boll weevil rice water weevil, granary weevil, rice weevil and other weevil pests, and soil inhabiting insects such as Western corn rootworm and other Diabrotica spp., Japanese beetle, European chafer and other coleopteran grubs, and wireworms;
adults and larvae of the orders Hemiptera and Homoptera including tarnished plant bug and other plant bugs (miridae), aster leafhopper and other leafhoppers (cicadellidae), rice planthopper, brown planthopper, and other planthoppers (fulgoroidea), psylids, whiteflies (aleurodidae), aphids (aphidae), scales (coccidae and diaspididae), lace bugs (tingidae), stink bugs (pentatomidae), cinch bugs and other seed bugs (lygaeidae), cicadas (cicadidae), spittlebugs (cercopids), squash bugs (coreidae), red bugs and cotton stainers (pyrrhocoridae);
adults and larvae of the order acari (mites) including European red mite, two spotted spider mite, rust mites, McDaniel mite, and foliar feeding mites;
adults and immatures of the order Orthoptera including grasshoppers;
adults and immatures of the order Diptera including leafminers, midges, fruit flies (tephritidae), and soil maggots;
adults and immatures of the order Thysanoptera including onion thrips and other foliar feeding thrips.
The compounds are also active against economically important livestock, household, public and animal health pests such as:
insect pests of the order Hymenoptera including carpenter ants, bees, hornets, and wasps;
insect pests of the order Diptera including house files, stable flies, face flies, horn flies, blow flies, and other muscoid fly pests, horse flies, deer flies and other Brachycera, mosquitoes, black flies, biting midges, sand flies, sciarids, and other Nematocera;
insect pests of the order Orthoptera including cockroaches and crickets;
insect pests of the order Orthoptera including the Eastern subterranean termite and other termites;
insect pests of the order Mallophaga and Anoplura including the head louse, body louse, chicken head louse and other sucking and chewing parasitic lice that attack man and animals;
insect pests of the order Siphonoptera including the cat flea, dog flea and other fleas.
The specific species for which control is exemplified are: fall armyworm, Spodoptera fruigiperda; tobacco budworm, Heliothis virescens; boll weevil, Anthonomus grandis; aster leafhopper, Macrosteles fascifrons; southern corn rootworm, Diabrotica undecimpunctata. The pest control protection afforded by these compounds of the present invention is not limited, however to these species.
Application
Arthropod pests are controlled and protection of agronomic crops, animal and human health is achieved by applying one or more of the Formula I compounds of this invention, in an effective amount, to the locus of infestation, to the area to be protected, or directly on the pests to be controlled. Because of the diversity of habitat and behavior of these arthropod pest species, many different methods of application are employed. A preferred method of application is by spraying with equipment that distributes the compound in the environment of the pests, on the foliage,-animal, person, or premise, in the soil or animal, to the plant part that is infested or needs to be protected. Alternatively, granular formulations of these toxicant compounds can be applied to or incorporated into the soil.
Other methods of application can also be employed including direct and residual sprays, aerial, baits, eartags, boluses, foggets, aerosols, and many others. The compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like which entice them to ingest or otherwise contact the compounds.
The compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, and synergists such as piperonyl butoxide often enhance the efficacy of the compounds of Formula I.
The rate of application of the Formula I compounds required for effective control will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, etc. In general, application rates of 0.05 to 2 kg of active ingredient per hectare are sufficient to provide large-scale effective control of pests in agronomic ecosystems under normal circumstances, but as little as 0.001 kg/hectare or as much as 8 kg hectare may be required. For nonagronomic applications, effective use rates will range from about 0.1 to 5 mg/square foot but as little as about 0.01 mg/square foot or as much as 15 mg/square foot may be required.
The following Examples demonstrate the control efficacy of compounds of Formula I on specific pests; see Tables 1 to 10 for compound descriptions. Compounds followed by a dash in the percent mortality column were either not screened or had less than 80% mortality on the test species.
EXAMPLE 8
Fall Armyworm
Test units, each consisting of an 8-ounce plastic cup containing a layer of wheat germ diet, approximately 0.5 cm thick, were prepared. Ten third-instar larvae of fall armyworm (Spodoptera frugiperda) were placed into each cup. Solutions of each of the test compounds (acetone/distilled water 75/25 solvent) were sprayed onto the cups, a single solution per set of three cups. Spraying was accomplished by passing the cups, on a conveyer belt, directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.5 pounds of active ingredient per acre (about 0.55 kg/ha) at 30 p.s.i. The cups were then covered and held at 27.degree. C. and 50% relative humidity for 72 hours, after which time readings were taken. The results are tabulated below.
______________________________________ Compound % Mort.______________________________________ 1 100 2 100 3 100 4 100 5 100 6 -- 7 100 8 100 9 100 10 100 11 100 12 100 13 100 14 100 15 100 16 100 17 100 18 67 19 60 20 47 21 100 22 87 23 100 24 87 25 100 26 100 27 100 28 -- 29 100 30 100 31 -- 32 -- 33 -- 34 100 35 -- 36 100 37 100 38 100 39 87 40 93 41 73 42 100 43 100 44 100 45 100 46 100 47 100 48 87 49 80 50 80 51 100 52 -- 53 -- 54 100 55 100 56 -- 57 80 58 -- 59 80 60 47 61 100 62 100 63 60 64 -- 65 -- 66 100 67 100 68 100 69 100 70 -- 71 40 72 100 73 93 74 27 75 20 76 -- 77 100 78 20 79 40 80 -- 81 87 82 33 83 80 84 60 85 80 86 -- 87 -- 88 73 89 -- .sup. 90.sup.1 100 91 100 92 100 93 100 94 100 95 93 96 -- 97 -- 98 100 99 93 100 60 101 -- 102 -- 103 -- 104 100 105 100 106 100 107 100 108 100 109 -- 110 100 111 100 112 100 113 33 114 -- 115 -- 116 -- 117 -- 118 -- 119 -- 120 -- 121 60 122 -- 123 -- 124 -- 125 -- 126 -- 127 -- 128 -- 129 -- 130 -- 131 -- 132 -- 133 -- 134 33 135 -- 136 -- 137 -- 138 33 139 -- 140 -- 141 -- 142 33 143 100 144 60 145 -- 146 -- 147 -- 148 -- 149 13 150 -- 151 -- 152 -- 153 -- 154 -- 155 -- 156 -- 157 -- 158 -- 159 -- 160 20 161 -- 162 -- 163 -- 164 -- 165 0 166 0 167 -- 168 47 169 -- 170 20 171 -- 172 -- 173 -- 174 -- 175 -- 176 67 177 87 178 33 179 -- 180 -- 181 100 182 -- 183 -- 184 -- 185 -- 186 -- 187 -- 188 -- 189 100 190 93 191 20 192 -- 193 60 194 -- 195 -- 196 -- 197 -- 198 -- 199 -- 200 -- 201 -- 202 100 203 -- 204 100 205 67 206 100 207 -- 208 -- 209 40 210 -- 211 -- 212 100 213 -- 214 -- 215 -- 216 73 217 -- 218 -- 219 -- 220 60 221 -- 222 100 223 -- 224 47 225 -- 226 -- 227 73 228 -- 229 -- 230 -- 231 -- 232 -- 233 -- 234 47 235 -- 236 -- 237 87 238 53 239 -- 240 93 241 100 242 100 243 13 244 -- 245 67 246 -- 247 -- 248 -- 249 -- 250 40 251 40 252 67 253 87 254 100 255 30 256 -- 257 -- 258 60 259 -- 260 -- 261 -- 262 -- 263 -- 264 -- 265 -- 266 -- 267 -- 268 -- 269 --______________________________________ 1. Test procedure was identical to that described except there was only one test cup.
EXAMPLE 0
Tobacco Budworm
The test procedure of Example 8 was repeated for efficacy against third-instar larvae of the tobacco budworm (Heliothis virescens) except that mortality was assessed at 48 hours. The results are tabulated below.
______________________________________ Compound % Mort.______________________________________ 1 100 1 100 2 100 3 73 4 100 5 93 6 -- 7 100 8 100 9 100 10 100 11 100 12 100 13 100 14 100 15 100 16 100 17 100 18 100 19 40 20 67 21 100 22 -- 23 -- 24 13 25 100 26 100 27 100 28 47 29 87 30 73 31 -- 32 -- 33 -- 34 -- 35 0 36 93 37 100 38 100 39 73 40 100 41 73 42 100 43 87 44 100 45 100 46 100 47 73 48 33 49 -- 50 60 51 -- 52 -- 53 -- 54 100 55 100 56 -- 57 -- 58 -- 59 100 60 -- 61 40 62 -- 63 0 64 -- 65 -- 66 100 67 100 68 87 69 100 70 93 71 -- 72 100 73 60 74 -- 75 -- 76 -- 77 100 78 20 79 -- 80 -- 81 -- 82 -- 83 -- 84 -- 85 -- 86 -- 87 -- 88 60 89 -- .sup. 90.sup.1 -- 91 100 92 100 93 100 94 87 95 80 96 -- 97 -- 98 100 99 100 -- 101 -- 102 -- 103 87 104 33 105 100 106 100 107 100 108 -- 109 -- 110 67 111 -- 112 -- 113 -- 114 -- 115 -- 116 -- 117 -- 118 -- 119 -- 120 -- 121 -- 122 -- 123 -- 124 -- 125 -- 126 -- 127 -- 128 -- 129 -- 130 -- 131 -- 132 0 133 -- 134 -- 135 -- 136 -- 137 -- 138 67 139 -- 140 27 141 -- 142 20 143 100 144 80 145 -- 146 -- 147 -- 148 -- 149 -- 150 -- 151 -- 152 -- 153 -- 154 -- 155 -- 156 -- 157 -- 158 -- 159 -- 160 -- 161 -- 162 -- 163 -- 164 -- 165 80 166 73 167 40 168 -- 169 -- 170 47 171 -- 172 27 173 -- 174 -- 175 -- 176 80 177 20 178 -- 179 73 180 -- 181 53 182 -- 183 -- 184 -- 185 -- 186 -- 187 -- 188 -- 189 -- 190 53 191 -- 192 -- 193 -- 194 13 195 -- 196 -- 197 -- 198 -- 199 -- 200 -- 201 -- 202 100 203 -- 204 67 205 67 206 100 207 33 208 -- 209 60 210 -- 211 -- 212 -- 213 -- 214 -- 215 -- 216 20 217 13 218 -- 219 -- 220 -- 221 -- 222 -- 223 -- 224 -- 225 -- 226 -- 227 -- 228 -- 229 -- 230 -- 231 -- 232 -- 233 -- 234 -- 235 -- 236 80 237 -- 238 60 239 80 240 -- 241 70 242 93 243 7 244 -- 245 -- 246 -- 247 -- 248 -- 249 -- 250 -- 251 -- 252 87 253 53 254 -- 255 7 256 33 257 47 258 33 259 -- 260 -- 261 -- 262 -- 263 -- 264 -- 265 -- 266 -- 267 -- 268 -- 269 --______________________________________
EXAMPLE 10
Aster Leafhopper
Test units were prepared from a series of 12-ounce cups, each containing oat (Avena sativa) seedlings in a 1-inch layer of sterilized soil. The test units were sprayed with individual solutions of the below-listed compounds. After the oats had dried from being sprayed, between 10 and 15 adult aster leafhoppers (Mascrosteles fascifrons) were aspirated into each of the covered cups. The cups were held at 27.degree. C. and 50% relative humidity for 48 hours, after which time mortality readings were taken. The following table depicts the activity of the compounds tested on aster leafhopper.
______________________________________ Compound % Mort.______________________________________ 1 -- 2 -- 3 -- 4 6 5 -- 6 -- 7 44 8 -- 9 100 10 85 11 -- 12 95 13 83 14 -- 15 73 16 75 17 -- 18 100 19 100 20 100 21 -- 22 -- 23 -- 24 -- 25 -- 26 -- 27 -- 28 -- 29 -- 30 -- 31 -- 32 -- 33 -- 34 -- 35 -- 36 -- 37 91 38 -- 39 -- 40 -- 41 60 42 98 43 89 44 -- 45 100 46 -- 47 100 48 -- 49 -- 50 -- 51 -- 52 -- 53 -- 54 -- 55 -- 56 -- 57 -- 58 -- 59 -- 60 12 61 96 62 -- 63 -- 64 -- 65 -- 66 50 67 -- 68 72 69 88 70 84 71 -- 72 -- 73 -- 74 -- 75 -- 76 -- 77 100 78 83 79 71 80 -- 81 100 82 -- 83 82 84 -- 85 -- 86 -- 87 -- 88 91 89 -- .sup. 90.sup.1 -- 91 -- 92 77 93 94 94 -- 95 74 96 -- 97 -- 98 -- 99 100 100 -- 101 -- 102 -- 103 -- 104 -- 105 100 106 84 107 100 108 71 109 -- 110 -- 111 -- 112 -- 113 -- 114 -- 115 -- 116 -- 117 -- 118 -- 119 -- 120 -- 121 -- 122 -- 123 -- 124 -- 125 -- 126 -- 127 -- 128 -- 129 -- 130 -- 131 -- 132 -- 133 -- 134 -- 135 -- 136 -- 137 -- 138 92 139 -- 140 -- 141 -- 142 -- 143 -- 144 -- 145 -- 146 -- 147 -- 148 -- 149 -- 150 -- 151 -- 152 -- 153 -- 154 -- 155 -- 156 -- 157 -- 158 -- 159 -- 160 -- 161 -- 162 -- 163 -- 164 -- 165 36 166 -- 167 -- 168 -- 169 -- 170 -- 171 -- 172 -- 173 -- 174 -- 175 -- 176 91 177 93 178 60 179 -- 180 -- 181 98 182 68 183 -- 184 -- 185 -- 186 -- 187 -- 188 -- 189 81 190 70 191 -- 192 95 193 -- 194 -- 195 -- 196 -- 197 -- 198 -- 199 -- 200 -- 201 -- 202 100 203 -- 204 94 205 -- 206 66 207 57 208 -- 209 -- 210 90 211 -- 212 88 213 -- 214 -- 215 -- 216 -- 217 -- 218 -- 219 -- 220 -- 221 -- 222 -- 223 -- 224 -- 225 -- 226 -- 227 -- 228 -- 229 -- 230 -- 231 -- 232 -- 233 -- 234 92 235 100 236 91 237 98 238 98 239 98 240 100 241 97 242 -- 243 -- 244 -- 245 -- 246 -- 247 -- 248 -- 249 -- 250 -- 251 -- 252 -- 253 -- 254 -- 255 -- 256 -- 257 -- 258 62 259 -- 260 -- 261 -- 262 -- 263 -- 264 -- 265 -- 266 -- 267 -- 268 -- 269 --______________________________________
EXAMPLE 11
Southern Corn Rootworm
Test units, each consisting of an 8-ounce plastic cup containing 1 sprouted corn seed, were prepared. Sets of three tests units were sprayed as described in Example 8 with individual solutions of the below-listed compounds. After the spray on the cups had dried, five third-instar larvae of the southern corn rootworm (Diabrotica undecimpunctata howardi) were placed into each cup. A moistened dental wick was inserted into each cup to prevent drying and the cups were then covered. The cups were then held at 27.degree. C. and 50% relative humidity for 48 hours, after which time mortality readings were taken. The results are tabulated below.
______________________________________ Compound % Mort.______________________________________ 1 100 2 100 3 100 4 100 5 100 6 -- 7 100 8 100 9 100 10 100 11 100 12 100 13 100 14 100 15 100 16 100 17 100 18 100 19 100 20 100 21 100 22 -- 23 100 24 93 25 -- 26 87 27 -- 28 -- 29 -- 30 87 31 100 32 -- 33 -- 34 100 35 -- 36 100 37 100 38 100 39 100 40 80 41 100 42 100 43 100 44 100 45 -- 46 100 47 -- 48 -- 49 -- 50 47 51 100 52 -- 53 -- 54 100 55 100 56 -- 57 -- 58 30 59 100 60 80 61 100 62 100 63 80 64 100 65 -- 66 100 67 100 68 100 69 100 70 100 71 47 72 73 73 -- 74 100 75 67 76 67 77 100 78 -- 79 100 80 -- 81 100 82 100 83 100 84 -- 85 -- 86 -- 87 93 88 100 89 100 .sup. 90.sup.1 -- 91 100 92 100 93 100 94 100 95 100 96 100 97 100 98 100 99 100 100 100 101 100 102 40 103 -- 104 -- 105 100 106 67 107 100 108 100 109 -- 110 100 111 100 112 100 113 -- 114 -- 115 -- 116 -- 117 -- 118 -- 119 -- 120 -- 121 -- 122 -- 123 -- 124 -- 125 -- 126 -- 127 -- 128 -- 129 -- 130 60 131 -- 132 -- 133 47 134 100 135 -- 136 100 137 100 138 100 139 100 140 93 141 100 142 -- 143 100 144 100 145 87 146 -- 147 100 148 47 149 -- 150 -- 151 -- 152 100 153 -- 154 -- 155 -- 156 -- 157 -- 158 -- 159 -- 160 0 161 -- 162 -- 163 -- 164 93 165 100 166 87 167 -- 168 100 169 100 170 100 171 -- 172 93 173 100 174 -- 175 -- 176 100 177 100 178 100 179 100 180 100 181 100 182 100 183 60 184 -- 185 100 186 100 187 -- 188 -- 189 100 190 100 191 100 192 100 193 100 194 100 195 -- 196 -- 197 -- 198 -- 199 -- 200 -- 201 -- 202 100 203 -- 204 100 205 100 206 100 207 93 208 100 209 100 210 100 211 100 212 100 213 -- 214 -- 215 -- 216 -- 217 -- 218 -- 219 -- 220 -- 221 -- 222 -- 223 -- 224 100 225 -- 226 -- 227 100 228 13 229 -- 230 -- 231 -- 232 -- 233 -- 234 100 235 100 236 100 237 100 238 100 239 100 240 100 241 100 242 100 243 -- 244 -- 245 27 246 -- 247 -- 248 -- 249 -- 250 -- 251 -- 252 100 253 100 254 80 255 100 256 -- 257 93 258 100 259 -- 260 93 261 -- 262 -- 263 -- 264 -- 265 -- 266 -- 267 -- 268 -- 269 --______________________________________
EXAMPLE 12
Boll Weevil
Five adult boll weevils (Anthonomus grandis) were placed into each of a series of 9-ounce cups. The test procedure employed was then otherwise the same as in Example 8 with three cups per treatment. Mortality readings were taken 48 hours after treatment. The results are tabulated below.
______________________________________ Compound % Mort.______________________________________ 1 87 2 66 3 20 4 100 5 80 6 -- 7 100 8 -- 9 100 10 100 11 100 12 100 13 100 14 100 15 100 16 100 17 100 18 100 19 100 20 100 21 100 22 93 23 100 24 100 25 -- 26 -- 27 -- 28 -- 29 100 30 100 31 100 32 -- 33 -- 34 100 35 -- 36 87 37 100 38 73 39 87 40 100 41 100 42 100 43 100 44 93 45 93 46 93 47 100 48 80 49 67 50 80 51 93 52 -- 53 -- 54 100 55 -- 56 -- 57 53 58 -- 59 100 60 -- 61 100 62 100 63 100 64 100 65 -- 66 100 67 100 68 100 69 93 70 53 71 -- 72 40 73 87 74 100 75 60 76 93 77 100 78 100 79 100 80 -- 81 100 82 100 83 100 84 100 85 80 86 -- 87 100 88 100 89 100 .sup. 90.sup.1 -- 91 93 92 100 93 100 94 100 95 100 96 73 97 67 98 100 99 100 100 100 101 100 102 40 103 -- 104 -- 105 100 106 100 107 100 108 100 109 -- 110 100 111 100 112 100 113 7 114 -- 115 -- 116 -- 117 -- 118 -- 119 -- 120 -- 121 -- 122 67 123 -- 124 -- 125 -- 126 -- 127 -- 128 -- 129 -- 130 -- 131 -- 132 -- 133 100 134 93 135 -- 136 -- 137 93 138 100 139 47 140 93 141 93 142 -- 143 100 144 100 145 -- 146 60 147 93 148 67 149 0 150 -- 151 -- 152 -- 153 -- 154 -- 155 -- 156 -- 157 -- 158 -- 159 -- 160 33 161 -- 162 -- 163 33 164 73 165 100 16 6 80 167 13 168 93 169 87 170 100 171 -- 172 -- 173 20 174 -- 175 -- 176 100 177 100 178 73 179 -- 180 -- 181 100 182 87 183 100 184 -- 185 87 186 73 187 -- 188 -- 189 100 190 93 191 100 192 100 193 100 194 60 195 -- 196 -- 197 -- 198 -- 199 -- 200 -- 201 -- 202 100 203 -- 204 100 205 100 206 100 207 87 208 100 209 100 210 93 211 100 212 100 213 -- 214 -- 215 -- 216 100 217 -- 218 -- 219 -- 220 -- 221 -- 222 -- 223 -- 224 -- 225 -- 226 -- 227 87 228 -- 229 -- 230 -- 231 -- 232 -- 233 -- 234 -- 235 33 236 80 237 -- 238 -- 239 -- 240 93 241 -- 242 100 243 -- 244 -- 245 27 246 -- 247 -- 248 -- 249 -- 250 -- 251 -- 252 100 253 100 254 100 255 93 256 100 257 87 258 93 259 -- 260 -- 261 -- 262 20 263 -- 264 -- 265 -- 266 -- 267 -- 268 -- 269 --______________________________________
Claims
  • 1. A compound of the formula ##STR28## wherein: Q is ##STR29## A is OCH.sub.2 or S(O).sub.q CH.sub.2, wherein, the carbon of each individually can be substituted with 1 to 2 substituents selected from 1 to 2 halogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.4 -C.sub.7 alkylcycloalkyl, C.sub.2 -C.sub.4 alkoxycarbonyl, or phenyl optionally substituted with 1 to 3 substituents independently selected from W;
  • R.sub.1 and R.sub.2 are independently R.sub.8, halogen, CN, NO.sub.2, N.sub.3, SCN, OR.sub.8, SR.sub.8, SOR.sub.8, SO.sub.2 R.sub.8, NR.sub.8 R.sub.9, C(O)R.sub.8, CO.sub.2 R.sub.8, C(O)NR.sub.8 R.sub.9, OC(O)R.sub.8, OCO.sub.2 R.sub.8, OC(O)NR.sub.8 R.sub.9, NR.sub.9 C(O)R.sub.8, NR.sub.9 C(O)NR.sub.8 R.sub.9, OSO.sub.2 R.sub.8, NR.sub.9 SO2R.sub.8; or when m is 2, R.sub.1, is optinally taken together to form a 5 or 6 membered fused ring as OCH.sub.2 O, OCH.sub.2 CH.sub.2 O or CH.sub.2 CH.sub.2 O each of which is optionally substituted with 1 to 4 halogen atoms or 1 to 2 methyl groups, or when n is 2, R.sub.2 is optionally taken together to form a 5 or 6 membered fused ring as OCH.sub.2 O, OCH.sub.2 CH.sub.2 O or CH.sub.2 CH.sub.2 O each of which can be substituted 1 to 4 halogens or 1 to 2 methyl groups;
  • R.sub.3 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.4 -C.sub.6 alkylcycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, OR.sub.8, S(O).sub.q R.sup.8, NR.sub.8 R.sup.9, CN, CO.sub.2 R.sub.8, C(O)R.sub.8, C(O)NR.sub.8 R.sub.9, C(S)NR.sub.8 R.sub.9, C(S)R.sub.8, C(S)SR.sub.8, phenyl optionally substituted with (R.sub.10).sub.p or benzyl optionally substituted with 1 to 3 substituents independently selected from W or R.sub.3 is C.sub.3 -C.sub.6 cycloalkyl optionally substituted with 1 to 2 halogens or 1 or 2 CH.sub.3 ;
  • R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 cyanoalkyl, phenyl optionally substituted with (R.sub.10).sub.p or benzyl optionally substituted with 1 to 3 substituents independently selected from W;
  • R.sub.5 and R.sub.6 are independently H, C.sub.1 -C.sub.22 alkyl, C.sub.2 -C.sub.22 alkoxyalkyl, C.sub.2 -C.sub.22 alkylcarbonyl, C.sub.2 -C.sub.22 alkoxycarbonyl, C.sub.2 -C.sub.22 haloalkyl carbonyl, C.sub.2 -C.sub.22 haloalkoxycarbonyl, SR.sub.11, CHO, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfonyl optionally substituted with 1 to 3 substituents independently selected from W; C.sub.7 -C.sub.15 phenoxycarbonyl optionally substituted with 1 to 3 substituents selected from W; C.sub.7 -C.sub.15 phenylcarbonyl optionally substituted with 1 to 3 substituents independently selected from W; C(O)CO.sub.2 C.sub.1 to C.sub.4 alkyl, C.sub.8 -C.sub.12 benzyloxycarbonyl optionally substituted with 1 to 3 substituents independently selected from W; or R.sub.5 and R.sub.6 are independently phenyl optionally substituted with 1 to 3 substituents independently selected from W, or benzyl optionally substituted with 1 to 3 substituents independently selected from W;
  • R.sub.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.4 -C.sub.7 halocycloalkylalkyl C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W or benzyl optionally substituted with 1 to 3 substituents independently selected from W;
  • R.sub.9 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl; or R.sub.8 and R.sub.9 is optionally taken together as (CH.sub.2).sub.4, (CH.sub.2).sub.5 or (CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2);
  • R.sub.10 is R.sub.8, halogen, CN, NO.sub.2 , N.sub.3 , SCN, OR.sub.8, SR.sub.8 , SOR.sub.8, SO.sub.2 R.sub.8, NR.sub.8 R.sub.9 , COR.sub.8, CO.sub.2 R.sub.8, CONR.sub.8 R.sub.9, SO.sub.2 NR.sub.8 R.sub.9, OC(O)R.sub.8, OCO.sub.2 R.sub.8, OC(O)NR.sub.8 R.sub.9, NR.sub.9 C(O)R.sub.8, NR.sub.9 C(O)NR.sub.8 R.sub.9, OSO.sub.2 R.sub.8, NR.sub.9 SO.sub.2 R.sub.8 or when p is 2, R.sub.10 is optionally taken together to form a 5 or 6 membered fused ring as OCH.sub.2 O, OCH.sub.2 CH.sub.2 O, or CH.sub.2 CH.sub.2 O each of which is optionally substituted with independently, 1 to 4 halogen atoms or 1 to 2 methyl groups;
  • R.sub.11 is C.sub.1 -C.sub.22 alkyl, C.sub.1 -C.sub.22 haloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W or R.sub.11, is NR.sub.12 C(O)R.sub.13, NR.sub.12 S(O).sub.a R.sub.13, ##STR30## R.sub.12 and R.sub.16 are independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.4 -C.sub.8 dialkylaminocarbonylalkyl, phenyl optionally substituted by 1 to 2 substituents selected from W, benzyl optionally substituted by 1 to 2 substituents selected from W and phenethyl optionally substituted by 1 to 2 substituents selected from W, or R.sub.12 -R.sub.16 is optionally taken together as (CH.sub.2).sub.4, (CH.sub.2).sub.5 or (CH.sub.2).sub.2 O(CH.sub.2).sub.2, each ring optionally substituted with 1 to 2 CH.sub.3 ;
  • R.sub.13 is F, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.8 dialkylamino, piperidinyl, pyrrolidinyl, morpholinyl, phenyl optionally substituted with 1 to 3 substituents selected from W, or R.sub.13 is C.sub.1 -C.sub.20 alkoxy C.sub.1 -C.sub.6 haloalkoxy or C.sub.1 -C.sub.4 alkoxy substituted with cyano, nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.4 -C.sub.8 alkoxyalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.2 -C.sub.3 alkoxycarbonyl, C.sub.3 -C.sub.5 dialkylaminocarbonyl or phenyl optionally substituted with 1 to 3 substituents independently selected from W; or R.sub.13 is phenoxy optionally substituted with 1 to 3 substituents selected from W;
  • R.sub.14 and R.sub.15 are independently selected from C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 haloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W or R.sub.14 and R.sub.15 is optionally taken together as (CH.sub.2).sub.2, (CH.sub.2).sub.3 or CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 ;
  • W is halogen, CN, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 alkylsulfonyl or C.sub.1 -C.sub.2 haloalkylsulfonyl;
  • m is 1 to 5;
  • n is 1 to 4;
  • q is 0 to 2;
  • p is 1 to 3;
  • a is 0 to 2;
  • X is O or S;
  • Y is O or S; and
  • Z is O or S;
  • with the proviso that provided that when A is OCH.sub.2 and the carbon of said OCH.sub.2 is substituted with phenyl optionally substituted with 1 to 3 substituents independently selected from W and R.sub.2 is OR.sub.8, then R.sub.8 is other than H, C.sub.1 -C.sub.6 alkyl and C.sub.3 -C.sub.8 alkoxycarbonylalkyl.
  • 2. A compound according to claim 1 wherein:
  • R.sub.1, R.sub.2 and R.sub.10 are R.sub.8, halogen, CN, NO.sub.2, OR.sub.8, SR.sub.8, SOR.sub.8, SO.sub.2 R.sub.8, NR.sub.8 R.sub.9, CO.sub.2 R.sub.8, SO.sub.2 NR.sub.8 R.sub.9, or when m, n or q is 2, then R.sub.1, R.sub.2 or R.sub.10 respectively is optionally taken together to form a 5 or 6 membered fused ring as OCH.sub.2 O, OCH.sub.2 CH.sub.2 O or CH.sub.2 CH.sub.2 O each of which is optionally substituted with 1 to 4 halogens or 1 to 2 methyl groups;
  • R.sub.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 cycloalkylalkyl, C.sub.3 -C.sub.6 halocycloalkylalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl optionally substituted with 1 to 2 substituents independently selected from W or benzyl optionally substituted with 1 to 2 substituents independently selected from W;
  • R.sub.5 and R.sub.6 are independently H, C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl, CHO, SR.sub.11, phenyl optionally substituted with 1 to 2 substituents independently selected from W, or benzyl optionally substituted with 1 to 2 substituents independently selected from W;
  • R.sub.11 is C.sub.1 -C.sub.3 alkyl, phenyl optionally substituted with 1 to 2 substituents independently selected from W, NR.sub.12 C(O)R.sub.13, NR.sub.12 S(O).sub.a R.sub.13, C(O)R.sub.13, NR.sub.12 R.sub.16 ; ##STR31## R.sub.12 and R.sub.16 are independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.8 alkoxycarbonyl- alkyl, phenyl, benzyl and phenethyl or each phenyl, benzyl and phenethyl optionally substituted with 1 to 2 substituents independently selected from W, or R.sub.12 and R.sub.16 can be taken together as (CH.sub.2).sub.4, (CH.sub.2).sub.5 or (CH.sub.2).sub.2 O(CH.sub.2).sub.2 ;
  • R.sub.14 and R.sub.15 are independently selected from C.sub.1 to C.sub.3 alkyl or phenyl;
  • m is 1 to 2;
  • n is 1 to 2;
  • p is 1 to 2;
  • q is 0; and
  • a is 2.
  • 3. A compound according to claim 2 wherein:
  • R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, CN, phenyl optionally substituted with (R.sub.10).sub.p or benzyl optionally substituted with 1 to 2 substituents independently selected from W;
  • R.sub.4 is H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl;
  • R.sub.5 is H, Me, CO.sub.2 Me, CO.sub.2 Et, SR.sub.11 or phenyl optionally substituted with 1 to 2 substituents independently selected from W;
  • R.sub.6 is H, Me, C(O)Me, CO.sub.2 Me or SR.sub.11 ;
  • R.sub.11 is C.sub.1 -C.sub.3 alkyl, or phenyl optionally substituted with Cl, NO.sub.2 or CH.sub.3 ;
  • R.sub.12 is C.sub.1 -C.sub.4 alkyl or phenyl optionally substituted with Cl or CH.sub.3 ;
  • R.sub.13 is C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 haloalkyl, dimethylamino, phenyl optionally substituted with Cl or CH.sub.3, or R.sub.13 is C.sub.1 -C.sub.4 alkoxy substituted with C.sub.2 -C.sub.4 alkoxy or 1 to 6 halogens; and
  • A is OCH.sub.2 or SCH.sub.2, wherein, each carbon is optionally substituted with C.sub.1 -C.sub.3 alkyl or phenyl, wherein, the phenyl is optionally substituted with W.
  • 4. An arthropodicidal composition comprising an arthropodicidally effective amount of a compound according to claim 1 and a carrier therefor.
  • 5. A method for controlling arthropods comprising applying to them or to their environment an arthropodicidally effective amount of a compound according to claim 1.
Parent Case Info

This application is a division of 07/971,008 filed Nov. 2, 1992 now U.S. Pat. No. 5,268,388, which is a divisional of 07/689,042 filed May 20, 1991 now U.S. Pat. No. 5,182,303, which was filed under 35 USC 371 based on PCT international application PCT/US89/05597 filed Dec. 20, 1989, which is a continuation of 07/436,361 filed Nov. 13, 1989 now abandoned, which is a continuation-in-part of 07/290,404 filed Dec. 27, 1988 now abandoned.

US Referenced Citations (2)
Number Name Date Kind
4547524 Kaneko Oct 1985
4593027 Mulder et al. Jun 1986
Foreign Referenced Citations (5)
Number Date Country
3913 Sep 1979 EPX
26040 Apr 1981 EPX
254461 Jan 1988 EPX
2239033 Feb 1973 DEX
8800197 Jan 1988 WOX
Non-Patent Literature Citations (5)
Entry
J. Indian Chem. Soc., 37, pp. 443-450 (1960).
Misra et al., J. Indian Chem. Soc., 52(10) pp. 981-982 (1975).
Chem. Abst. vol. 84, 73957m (1976).
Lundquist, J. Chem. Soc. (C); pp. 63-66 (1970).
Treibs et. al., Berichte, 86(5), pp. 616-625 (1953).
Divisions (2)
Number Date Country
Parent 971008 Nov 1992
Parent 689042 May 1991
Continuations (1)
Number Date Country
Parent 436361 Nov 1989
Continuation in Parts (1)
Number Date Country
Parent 290404 Dec 1988