Abstract:
A fungicidal method which comprises applying to the locus of a plant pathogen a fungicidally effective but non-phytotoxic amount of a compound of the formula (1) ##STR1## wherein: R 1  to R 4  are independently 
     H, halo, (C 1  -C 4 ) alkyl, branched (C 3  -C 4 ) alkyl, halo (C 1  -C 4 ) alkyl, (C 1  -C 4 ) alkoxy, NO 2 , or HN 2 , at least two of R 1  to R 4  being H, 
     or one of R 2  to R 4  is --NR 7  --Y--Ar or O--Y--Ar and the rest of R 1  to R 4  are H; 
     W is N, or CR 5  ; 
     R 5  is H, CH 3 , Cl, O--Y--Ar, or --NR 7  --Y--Ar; 
     R 6  is H, CH 3 , Cl, or Br; 
     A is --O--Alk or --X--Y--Ar; 
     Alk is a C 2  -C 18  saturated or unsaturated hydrocarbon chain, straight chain or branched, optionally substituted with halo, halo (C 1  -C 4 ) alkoxy, (C 3  -C 8 ) cycloalkyl, hydroxy, or acetyl; 
     X is O, NR 7 , or CR 8  R 9 , provided that if one of R 2  to R 5  is NR 7  --Y--Ar or O--Y--Ar, then X--Y--Ar is an identical group; 
     R 7  is H, (C 1  -C 4 ) alkyl, or acetyl; 
     R 8  and R 9  are independently H, (C 1  -C 4 ) alkyl, halo, or OH, or R 8  and R 9  combine to form a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms; 
     Y is an alkylene chain 2 to 8 carbon atoms long that optionally includes an O, S, SO, SO 2 , or NR 7  group, and optionally includes a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms, and optionally is substituted with (C 1  -C 3 ) alkyl, (C 1  -C 4 ) alkenyl, phenyl, (C 3  -C 8 ) cycloalkyl, hydroxy, halo, or acetyl; and 
     Ar is an aryl group.

Description:
RELATED APPLICATIONS 
     This application is a continuation-in-part of U.S. Appln. Ser. No. 07/150,366, filed Jan. 29, 1988, now abandoned. 
    
    
     BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     This invention provides new compounds that have excellent plant fungicide activity. Some of the compounds have also demonstrated insecticidal and miticidal activity. The invention also provides compositions and combination products that contain a compound of the invention as active ingredient. The invention also provides fungicidal, miticidal, and insecticidal methods. 
     There is an acute need for new fungicides, insecticides, and miticides, because target pathogens are rapidly developing resistance to currently used pesticides. Widespread failure of N-substituted azole fungicides to control barley mildew was observed in 1983, and has been attributed to the development of resistance. At least 50 species of fungi have developed resistance to the benzimidazole fungicides. The field performance of DMI (demethylation inhibitor) fungicides, which are now widely relied on to protect cereal crops from powdery mildew, has declined since they were introduced in the 1970&#39;s. Even recent fungicides, like the acylalanines, which initially exhibited excellent control of potato late blight and grape downy mildew in the field, have become less effective because of widespread resistance. Similarly, mites and insects are developing resistance to the miticides and insecticides in current use. Resistance to insecticides in arthropods is widespread, with at least 400 species resistant to one or more insecticides. The development of resistance to some of the older insecticides, such as DDT, the carbamates, and the organophosphates, is well known. But resistance has even developed to some of the newer pyrethroid insecticides and miticides. Therefore a need exists for new fungicides, insecticides, and miticides. 
     SUMMARY OF THE INVENTION 
     This invention provides compounds of the formula (1): ##STR2## wherein: R 1  to R 4  are independently 
     H, halo, (C 1  -C 4 ) alkyl, branched (C 3  -C 4 ) alkyl, halo (C 1  -C 4 ) alkyl, (C 1  -C 4 ) alkoxy, NO 2 , or NH 2 , at least two of R 1  to R 4  being H, 
     or one of R 2  to R 4  is --NR 7  --Y--Ar or O--Y--Ar and the rest of R 1  to R 4  are H; 
     W is N, or CR 5  ; 
     R 5  is H, CH 3 , Cl, O--Y--Ar, or --NR 7  --Y--Ar; 
     R 6  is H, CH 3 , Cl or Br; 
     A is --O--Alk or --X--Y--Ar; 
     Alk is a C 2  -C 18  saturated or unsaturated hydrocarbon chain, straight chain or branched, Optionally substituted with halo, halo (C 1  -C 4 ) alkoxy, (C 3  -C 8 ) cycloalkyl, hydroxy, or acetyl; 
     X is O, NR 7 , or CR 8  R 9 , provided that if one of R 2  to R 5  is NR 7  --Y--Ar or O--Y--Ar,--then X--Y--Ar is an identiR; 
     R 7  is H, (C 1  -C 4 ) alkyl, or acetyl; 
     R 8  and R 9  are independently H, (C 1  -C 4 ) alkyl, (C 1  -C 4 ) acyl, halo, or OH, or R 8  and R 9  combine to form a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms; 
     Y is an alkylene chain 2 to 8 carbon atoms long, that optionally includes an O, S, SO, SO 2 , or NR 7  group, and optionally includes a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms, and optionally is substituted with (C 1  -C 3 ) alkyl, (C 2  -C 4 ) phenyl, (C 3  -C 8 ) cycloalkyl, hydroxy, halo, or (C 1  -C 4 ) acyl; and 
     Ar is 
     1,3-benzodioxolyl 
     fluorenyl, 
     pyridyl 
     substituted pyridyl, 
     indolyl, 
     furanyl, 
     substituted furanyl, 
     thienyl, optionally substituted with CH 2  or Cl, 
     thiazolyl, 
     cyclopentyl, 
     1-methylcyclopentyl, 
     cyclohexenyl (tetrahydrophenyl), 
     cyclohexyl (hexahydrophenyl), 
     naphthyl, 
     substituted naphthyl, 
     dihydronaphthyl, 
     tetrahydronaphthyl, 
     decahydronaphthyl, or 
     a group of the formula (2): ##STR3## where R 10  to R 14  are independently H, halo, I, (C 1  -C 10 ) branched (C 3  -C 6 ) alkyl, halo (C 1  -C 7 ) alkyl, (C 1  -C 7 ) alkoxy, halo (C 1  -C 7 ) alkoxy, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, NO 2 , NH 2 , acetoxy, OH, CN, SiR 15  R 16  R 17 , or OSiR 15  R 16  R 17 , where R 15 , R 16 , and R 17  are independently (C 1  -C 4 ) alkyl or (C 3  -C 4 ) branched alkyl, phenyl, or substituted phenyl, provided that unless each of R 10  to R 14  is F, CH 3 , or H, then at least two of R 10  to R 14  are H; 
     or an acid addition salt of a compound of formula (1) 
     or an N-oxide of a compound of formula (1) when W is CR 5   
     provided that the following compounds are excluded: 
     (1) N-[4-(4-chlorophenyl)butyl]-7-chloro-4-quinolinamine; 
     (2) N-(2-phenylethyl)-4-quinolinamine. 
     The final proviso excludes compounds that are known per se or that could be considered similar to known compounds. 
     The fungicidal combinations of the invention comprise at least 1% by weight of a compound of formula (1), or N-[4-(4-chlorophenyl)butyl]-7-chloro-4-quinolineamine or N-(2-phenylethyl)-4-quinolinamine, in combination with a second fungicidal compound. 
     The fungicidal compositions of the invention comprise a disease inhibiting and phytologically acceptable amount of a compound of formula (1), or N-[4-(4-chlorophenyl)butyl]-7-chloro-4-quinolinamine, or N-(2-phenylethyl)-4-quinolinamine, in combination with a phytologically-acceptable carrier. 
     The fungicidal method of the invention comprises applying to the locus of a plant pathogen a disease inhibiting and phytologically acceptable amount of a compound of the formula (1), or N-[4-(4-chlorophenyl)butyl]7-chloro-4-quinolinamine, or N-(2-phenylethyl)-4-quinolinamine. 
     The insecticidal or miticidal combinations of the invention comprise at least 1% by weight of a compound of formula (1) in combination with a second insecticide or miticide. 
     The insecticide or miticide compositions of the invention comprise an insect or mite inactivating amount of a compound of formula (1) in combination with a phytologically-acceptable carrier. 
     The insecticide and miticide methods of the invention comprise applying to a locus of an insect or mite an insect or mite inactivating amount of a compound of formula (1), or of a combination described above. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     Throughout this document, all temperatures are given in degrees Celsius, and all percentages are weight percentages unless otherwise stated. 
     The terms &#34;(C 1  -C 3 ) alkyl&#34;, &#34;(C 1  -C 4 ) alkyl&#34;, and &#34;(C 1  -C 10 ) aIkyl&#34;, when used alone, refer to straight chain alkyl radicals. 
     The terms &#34;branched (C 3  -C 4 ) alkyl&#34;, and &#34;branched (C 3  -C 6 ) alkyl&#34; refer to all alkyl isomers containing the designated number of carbon atoms, excluding the straight chain isomers. 
     The terms &#34;(C 1  -C 4 ) alkoxy&#34; and &#34;(C 1  -C 7 ) alkoxy&#34; refer to straight or branched chain alkoxy groups. 
     The term &#34;halo&#34; used alone or in combination with other terms refers to F, Cl, or Br; 
     The term &#34;halo (C 1  -C 7 ) alkyl&#34; refers to a (C 1  -C 7 ) alkyl group, straight chain or branched, substituted with one or more halo groups. 
     The term &#34;substituted phenyl&#34; used alone or in combination with other terms, as in &#34;substituted phenylthio&#34; or &#34;substituted phenylsulfonyl&#34; , refers to phenyl substituted with up to three groups selected from halo, I, (C 1  -C 10 ) alkyl, branched (C 3  -C 6 ) alkyl, halo (C 1  -C 7 ) alkyl, hydroxy (C 1  -C 7 ) alkyl, (C 1  -C 7 ) alkoxy, halo (C 1  -C 7 ) alkoxy, phenoxy, phenyl, NO 2 , OH, CN, (C 1  -C 4 ) alkanoyloxy, or benzyloxy. 
     The term &#34;substituted phenoxy&#34; refers to phenoxy substituted with up to three groups selected from halo, I, (C 1  -C 10 ) alkyl, branched (C 3  -C 6 ) alkyl, halo (C 1  -C 7 ) alkyl, hydroxy (C 1  -C 7 ) alkyl, (C 1  -C 7 ) alkoxy, halo (C 1  -C 7 ) alkoxy, phenoxy, phenyl, NO 2 , OH, CN, (C 1  -C 4 ) alkanoyloxy, or benzyloxy. 
     The terms &#34;substituted naphthyl&#34;, &#34;substituted pyridyl&#34; and &#34;substituted furanyl&#34; refer to these ring systems substituted with halo, halo (C 1  -C 4 ) alkyl, CN, NO 2 , (C 1  -C 4 ) alkyl, (C 3  -C 4 ) branched alkyl, phenyl, (C 1  -C 4 ) alkoxy, or halo (C 1  -C 4 ) alkoxy. 
     The term &#34;unsaturated hydrocarbon chain&#34; refers to a hydrocarbon chain containing one or two sites of unsaturation. 
     The term &#34;HPLC&#34; refers to high-performance liquid chromatography. 
     Compounds 
     While all of the compounds of the invention are useful fungicides, certain classes are preferred for reasons of greater efficacy or ease of synthesis, viz: 
     1. compounds of formula (1) where W is CR 5  (i.e., substituted quinolines); 
     2. compounds of preferred class (1) where R 6  is H; 
     3. compounds of formula (1) where R 6  is H; 
     4. compounds of formula (1) where at least three of R 1  to R 4  are H; 
     5. compounds of preferred class (4) where R is F (i.e., 8-fluoroquinolines); 
     6. compounds of preferred class (4) where Rs is F (i.e., 7-fluoroquinolines); 
     7. compounds of preferred class (4) where Rs is Cl (i.e., 7-chloroquinolines); 
     8. compounds of preferred class (4) where Rz is F (i.e., 6-fluoroquinolines); 
     9. compounds of formula (1) where Y is an alkylene chain 2 to 4 carbon atoms long. 
     10. compounds of preferred class (9) where Y is --(CH 2 ) 2  --; 
     11. compounds of formula (1) where Ar is 
     12. compounds of formula (1) where Ar is 
     13. compounds of formula (1) where Ar is 
     14. compounds of formula (1) where Ar is cyclohexenyl; 
     15. compounds of formula (1) where Ar is a substituted phenyl group of formula (2); 
     16. compounds of preferred class (15) where at least three of R 10  to R 14  are H; 
     17. compounds of preferred class (15) where four R 10  to R 14  are H; 
     18. compounds of preferred class (17) wherein one of R 10  to R 14  is Cl; 
     19. compounds of preferred class (18) where R 12  is Cl; 
     20. compounds of preferred class (17) wherein one of R 10  to R 14  is CF 3  ; 
     21. compounds of preferred class (17) wherein one of R 10  to R 14  is (C 1  -C 4 ) alkyl; 
     22. compounds of preferred class (21) wherein one of R 10  to R 14  is methyl; 
     23. compounds of preferred class (22) wherein R 12  is methyl; 
     24. compounds of preferred class (17) wherein one of R 10  to R 14  is branched (C 3  -C 6 ) alkyl; 
     25. compounds of preferred class (24) wherein R 12  is t-butyl; 
     26. compounds of preferred class (24) wherein R 12  is i-propyl; 
     27. compounds of preferred class (17) wherein one of R 10  to R 14  is phenyl or substituted phenyl; 
     28. compounds of preferred class (27) wherein R 12  is phenyl; 
     29. compounds of preferred class (17) wherein one of R 10  to R 14  is phenoxy or substituted phenoxy; 
     30. compounds of preferred class (29) wherein R 12  is phenoxy. 
     Compounds exhibiting particularly excellent activity against downy mildew include: 
     8-fluoro-N-(2-phenylethyl)-4-quinolinamine; 
     8-fluoro-N-[2-(4-phenyl-2-thiazolyl)ethyl]-4-quinolinamine; 
     8-fluoro-N-[2-[2-(trifluoromethyl)phenyl]ethyl]-4quinolinamine; 
     N-[2-(4-chlorophenyl)ethyl]-6-methyl-4-quinolinamine; 
     8-chloro-N-(2-phenylethyl)-4-quinolinamine; 
     8-fluoro-N-[2-(4-phenyl-2-thiazolyl)ethyl]-4-quinolinamine; 
     8-fluoro-N-[2-(2-naphthyl)ethyl]-4-quinolinamine; 
     8-fluoro-N-[2-[3-(trifluoromethyl)phenyl]ethyl]-4quinolinamine; 
     7-chloro-N-[2-(1-cyclohexenyl)ethyl]-4-quinolinamine; 
     N-[2-[4-(1-methylethyl)phenyl]ethyl]-8-fluoro-4quinolinamine; 
     8-fluoro-N-[2-(2-thienyl)ethyl]-4-quinolinamine; 
     4-[2-(3-chlorophenyl)ethoxy]-8-fluoroquinoline; 
     8-fluoro-4-[2-(3-(trifluoromethyl)phenyl)ethoxy]quinoline; 
     4-[2-(4-methylphenyl)ethoxy]quinoline; 
     8-fluoro-4-[2-(4-methylphenyl)ethoxy]quinoline; and 
     4-[2-[4-(t-butyl)phenyl]ethoxy]-8-fluoroquinoline; 
     Compounds exhibiting particularly excellent activity against rice blast include: 
     N-[2-(4-chlorophenyl)ethyl]-N-(8-fluoro-4-quinolinyl)acetamide; 
     N-[2-[4-(i-propyl)-phenyl]ethyl]-8-fluoro-4-quinolin 
     8-fluoro-N-[2-(1,1&#39;-biphenyl)-4-yl-ethoxy]quinoline; 
     8-fluoro-4-[2-(3-(trifluoromethyl)phenyl)ethoxy]quinoline; 
     8-fluoro-4-[2-(2-naphthyl)ethoxy]quinoline; 
     8-fluoro-4-[2-(4-methylphenyl)ethoxy]quinoline; and 
     8-fluoro-4-[3-(4-(t-butyl)phenyl)propyl]quinoline; 
     Compounds exhibiting particularly excellent activity against a broad spectrum of plant pathogens include: 
     8-fluoro-N-[2-(3-phenoxyphenyl)ethyl]-4-quinolinamine; 
     N-[2-[4-(i-propyl)phenyl]ethyl]-8-fluoro-4-quinolin 
     N-[2-(1,1&#39;-biphenyl)-3-ylethyl]-8-fluoro-4-quinolin 
     N-[2-(2,4-dichlorophenyl)ethyl]-8-fluoro-4-quinolin 
     8-fluoro-4-[3-(4-(t-butyl)phenyl)propyl]quinoline; 
     8-fluoro-4-[3-(4-(i-propyl)phenyl)propyl]quinoline; 
     8-fluoro-4-[2-(2-(trifluoromethyl)phenyl)ethoxy]quinoline; 
     4-[2-(4-chlorophenyl)ethoxy]-8-fluoroquinoline; 
     4-[2-(4-methylphenyl)ethoxy]quinoline; 
     8-fluoro-4-[2-(4-methylphenyl)ethoxy]quinoline; 
     8-fluoro-4-(2-phenylethoxy)quinoline; 
     8-fluoro-4-[2-(3-methylphenyl)ethoxy]quinoline; 
     8-fluoro-4-[2-(2-fluorophenyl)ethoxy]quinoline; 
     8-fluoro-4-[2-(2-methoxyphenyl)ethoxy]quinoline; and 
     8-fluoro-4-[2-(4-(i-propyl)phenyl)ethoxy]quinoline; 
     Compounds exhibiting particularly excellent activity as miticides include: 
     8-fluoro-N-[2-(4-iodophenyl)ethyl]-4-quinolinamine; 
     N-[2-(4-bromophenyl)ethyl]-8-fluoro-4-quinolinamine; 
     N-[2-(4-chlorophenyl)ethyl)-8-fluoro-4-quinolinamine; 
     N-[2-(4-chlorophenyl)ethyl]-N-ethyl-8-fluoro-4-quinolinamine; 
     N-3-(1,1&#39;-biphenyl)-4-ylpropyl]-8-fluoro-4-quinolin 
     8-fluoro-N-[2-(4-phenoxyphenyl)ethyl]-4-quinolinamine; 
     N-2-4-(t-butyl)phenyl]ethyl]-8-fluoro-4-quinolin 
     N-[2-[4-(i-propyl)phenyl]ethyl]-8-fluoro-4-quinolin 
     N-2-(4-chlorophenyl)ethyl]-6-fluoro-4-quinolinamine; 
     8-fluoro-N-[2-(1,1&#39;-biphenyl)-4-yl-ethoxy]quinoline; 
     4-[2-(3-chlorophenyl)ethoxy]-8-fluoroquinoline; 
     4-2-[4-(t-butyl)phenyl]ethoxy]-8-fluoroquinoline; 
     8-fluoro-4-[2-(4-(i-propyl)phenyl)ethoxy]quino 
     8-fluoro-4-2-(3-(trifluoromethyl)phenyl)ethoxy]quinoline; 
     8-fluoro-4-2-(4-methoxyphenyl)ethoxy]quinoline; 
     8-fluoro-4-2-(3-phenoxyphenyl)ethoxy]quinoline; 
     8-fluoro-4-2-(2-naphthyl)ethoxy]quinoline; 
     7-fluoro-4-2-(1,1&#39;-biphenyl)-2-yl-ethoxy]quinoline; 
     7-chloro-4-[2-(1,1&#39;-biphenyl)-4-yl-ethoxy]quinoline; 
     4-chloro-4-[2-(4-(t-butyl)phenyl)ethoxy]quinoline; 
     4-[2-(4-(t-butyl)phenyl)ethoxy]-7-fluoroquinoline; 
     8-2-(1,1&#39;-biphenyl)-4-ylethoxy]-7-fluoroquinoline; 
     8-fluoro-4-(3-phenylpropyl)quinoline; 
     8-fluoro-4-[3-(4-methylphenyl)propyl]quinoline; and 
     8-fluoro-4-[3-[3-(trifluoromethyl)phenyl]propyl]quinoline. 
     Synthesis 
     The compounds of this invention are made using well known chemical procedures. The required starting materials are commercially available, or they are readily synthesized using standard procedures. 
     Synthesis of Compounds Wherein A is O--Y--Ar or --O--Alk 
     The compounds of formula (1) wherein A is O--Y--Ar or O--Alk were made by condensing a compound of formula (3): ##STR4## where R 1  to R 4  are as previously defined, R 6 , is H or CH 3 , and W&#39; is N or CR 5  &#39;, where R 5  &#39; is H, Cl, or CH 3 , with an alcohol of the formula (4a or 4b): 
     
         HO--Y--Ar                                                  (4a) 
    
     
         HO--Alk                                                    (4b) 
    
     where 
     Y, Ar, and Alk are as previously defined. 
     The reaction is preferably carried out in the presence of a strong base, such as sodium hydride, in an inert organic solvent, such as DMF, at a temperature in the range of 0° to 25° C. 
     Synthesis of Compounds Wherein A is NR 7  --Y--Ar 
     The compounds of formula (1) wherein A is NR 7  --Y--Ar were prepared by condensing a compound of formula (3) with an amine of the formula (5) ##STR5## where R 7  is H or (C 1  -C 4 ) alkyl, and Y and 
     Ar are as previously defined. 
     The chloride of formula (3) is allowed to react with an appropriate amine, preferably at elevated temperature (100°-180° C.), and preferably in the presence of an acid accepter, such as triethylamine. The reaction may be carried out neat, or in an inert organic solvent. 
     Compounds where R 7  is acetyl were prepared by reacting amines of formula (1) where R 7  is H, with an acylating agent, such as an acetyl chloride or acetic anhydride. In cases where the starting material of formula (3) is one wherein W&#39; is CCl, a mixture of products is obtained, which are separable using HPLC. 
     Synthesis of Compounds Wherein A is CR 8  R 9  --Y--Ar 
     The compounds of formula (1) wherein A is CR 8  R 9  --Y--Ar can be made using the process described in J. Heterocyclic Chemistry, Vol. 14, p. 1081-1083 (1977) by A. Scoville and F. X. Smith. This process entails preparation of a 5-substituted-5-(4-quinolyl)barbituric acid of the formula (6) ##STR6## which is then hydrolyzed and decarboxylated by dissolving the intermediate in a solution of sodium hydroxide and water, refluxing, then making the solution slightly acidic with hydrochloric acid and again refluxing. 
     Derivatives 
     The compounds of formula (1) wherein R 6  is Cl are prepared by halogenating a compound of formula (1) wherein R 6  is H with POCl 3  /PCl 5 . 
     The compounds of formula (1) wherein Rs is Br are prepared by reacting a compound of formula (1) wherein R 6  is H with Br 2  in acetic acid. 
     N-oxides of the compounds of formula (1) are prepared by reacting the compound of formula (1) with an oxidizing agent, such as 3-chloroperoxybenzoic acid or hydrogen peroxide, in a non-reactive organic solvent, such as methylene chloride or chloroform, at -20° C. to room temperature, preferably at about 0° C. 
     The acid addition salts of compounds of formula (1) are obtained in the usual way. 
     Accordingly, the invention also provides a process for preparing a compound of formula (1) which comprises: 
     (a) condensing a compound of formula (3): ##STR7## where R 1  to R 4  are as previously defined, R 6  &#39; is H or CH 3 , and W&#39; is N or CR 5  &#39;, where R 5  &#39; is H, Cl, or CH 3 , with an alcohol of the formula (4a or 4b): 
     
         HO--Y--Ar,                                                 (4a) 
    
     
         HO--Alk (4b) 
    
     where 
     Y, Ar, and Alk are as previously defined to provide a compound of formula (1) wherein A is O--Y--Ar or O--Alk; or 
     (b) condensing a compound of formula (3) with an amine of the formula (5) ##STR8## where R 7  is H or (C 1  -C 4 ) alkyl, and Y and 
     Ar are as previously defined to provide a compound of formula (1) wherein A is --NR 7  --Y--Ar; or 
     (c) reacting an amine of formula (1) where R 7  is H, with acetyl chloride or acetic anhydride to provide a compound of formula (1) wherein A is --NR 7  --Y--Ar where R 7  is acetyl; or 
     (d) hydrolyzing and decarboxylating a compound of the formula (6) ##STR9## to provide a compound of formula (1) wherein A is --CR 8  R 9  --Y--Ar or 
     (e) halogenating a compound of formula (1) wherein R 6  is H with POCl 3  /PCl 5  to provide a compound of formula (1) wherein R 6  is Cl; or 
     (f) reacting a compound of formula (1) wherein R 6  is H with Br 2  in acetic acid to provide a compound of formula (1) wherein R 6  is Br; or 
     (g) oxidizing a compound of formula (1) wherein W is CRs to provide the corresponding N-oxide. 
     Preparation of Quinoline Starting Materials 
     Quinoline starting materials can be synthesized using a variety of known procedures. 
     Organic Syntheses, collective volume 3, 1955, pp. 272-75, gives a procedure for preparing 4,7-dichloroquinoline, and other polysubstituted quinolines. Another general procedure is described in Tetrahedron, vol. 41, pp. 3033-36 (1985). 
     Many of the quinoline starting materials used in the following examples were prepared by the protocol shown in the following reaction scheme ##STR10## 
     In cases where mixtures of isomeric products were obtained, the mixture of substituted 4-quinolones was chlorinated under standard conditions, and the 4-chloroquinolines were separated by liquid chromatography. 
     Preparation of Cinnoline Starting Materials 
     Cinnoline analogs are prepared via published methods. (C. M. Atkinson and J. C. Simpson - J. Chem. Soc. London, 1947, 232). The substituted 2-amino-acetophenone is diazotized at 0°-5° C. in water using sodium nitrite and mineral acid, and the intermediate diazonium salt is trapped by the enolic component of the ketone to provide the requisite 4-hydroxycinnoline. Routine chlorination provides the desired intermediates. 
     EXAMPLES 1 TO 328 
     Tables 1-12 identify compounds actually prepared by the above described general procedures, and give each compound&#39;s melting point. Specific illustrative preparations of the compounds of Examples 4, 10, 25, 69, 97, 154, 159, 173, 181, 186, 209, 212, 221, 238, 251, and 261 follow the table. 
     
                       TABLE 1______________________________________N-(2-phenylethyl)-4-quinolinaminesEXAMPLENUMBER   COMPOUND              M.P.______________________________________ 1       6-methoxy-N-(2-phenylethyl)-4-                          NA    quinolineamine 2*      N-(2-phenylethyl)-4-quinolin-                          159-160° C.    amine 3       6-ethyl-N-(2-phenylethyl)-4-                          119-120° C.    quinolinamine 4       N-ethyl-N-(2-phenylethyl)-4-                          oil    quinolinamine 5       8-fluoro-N-(2-phenylethyl)-                          149-150° C.    4-quinolinamine 6       2-methyl-N-(2-phenylethyl)-                          153-154° C.    4-quinolinamine 7       6,8-difluoro-N-(2-phenylethyl)-                          196-197° C.    ethyl)-4-quinolinamine 8       7-fluoro-N-(2-phenylethyl)-                          160-161° C.    4-quinolinamine 9       6-fluoro-N-(2-phenylethyl)-                          163-164° C.    4-quinolinamine10       N-[2-(4-chlorophenyl)ethyl]-                          oil    N-(8-fluoro-4-quinolinyl)-    acetamide11       8-fluoro-N-[2-(4-iodo-                          221-223° C.    phenyl)ethyl]-4-quinolin-    amine12       N-[2-(4-bromophenyl)ethyl]-                          235-238° C.    6,8-difluoro-4-quinolinamine13       N-[2-(4-bromophenyl)ethyl]-                          188-190° C.    8-(trifluoromethyl)-4-quinolin-    amine14       N-[2-(4-chlorophenyl)ethyl]-                          123-125° C.    6-methyl-4-quinolinamine15       N-[2-(4-chlorophenyl)ethyl]-                          113-115° C.    6,8-dimethyl-4-quinolinamine16       N-[2-(4-chlorophenyl)ethyl]-                          155-157° C.    6-methoxy-4-quinolinamine17       N-(2-phenylethyl)-7-(tri-                          138-139° C.    fluoromethyl)-4-quinolinamine18       N-[2-(4-bromophenyl)ethyl]-                          176-177° C.    4-quinolinamine19       N-[2-(4-methylphenyl)ethyl]-                          159-160° C.    4-quinolinamine20*      N-[2-(4-chlorophenyl)ethyl]-                          162-163° C.    4-quinolinamine21       N-(2-phenylpropyl)-4- 126-127°  C.    quinolinamine22       N-[2-(4-methoxyphenyl)-                          127-128° C.    ethyl]-4-quinolinamine23       N-(2,2-diphenylethyl)-4-                          154-155° C.    quinolinamine24       N-(1-methyl-2-phenylethyl)-                          132-133° C.    4-quinolinamine25       2-chloro-N-(2-phenylethyl)-                          132-133° C.    4-quinolinamine26       α-[(4-quinolinylamino)-                          195-197° C.    methyl]benzenemethanol27       8-methyl-N-(2-phenylethyl)-                          127-128° C.    4-quinolinamine28       6,8-dimethyl-N-(2-phenyl-                          114-115° C.    ethyl)-4-quinolinamine29       8-ethyl-N-(2-phenyl)-  98-99° C.    4-quinolinamine30       6-methyl-N-(2-phenylethyl)-                          124-125° C.    4-quinolinamine31       7-chloro-N-(2-phenylethyl)-                          137-138° C.    4-quinolinamine32       7,8-dimethyl-N-(2-phenyl-                          183-185° C.    ethyl)-4-quinolinamine33       8-chloro-N-(2-phenylethyl)-                          156-157° C.    4-quinolinamine34       N-(2,2-diphenylpropyl)-4-                          110-111° C.    quinolinamine35       N-[2-(4-fluorophenyl)ethyl]-                          121-122° C.    4-quinolinamine36       8-fluoro-N-[2-(4-methoxy-                          165-167° C.    phenyl)ethyl]-4-quinolinamine37       7-chloro-N-[2-(4-chloro-                          190-192° C.    phenyl)ethyl]-4-quinolinamine38       N-[2-(3,4-dimethoxyphenyl)-                          127-130° C.    ethyl]-8-fluoro-4-quinolin-    amine39       8-fluoro-N-[2-(3-phenoxy-                           83-85° C.    phenyl)ethyl]-4-quinolin-    amine40       6,8-difluoro-N-(2-[1,1&#39;-                          216-218° C.    biphenyl]-4-ylethyl)-4-    quinolinamine41       N-[2-(4-chlorophenyl)ethyl]-                          218-220° C.    6,8-difluoro-4-quinolinamine42       N-[2-(4-methoxyphenyl)ethyl]-                          107-109° C.    7-(trifluoromethyl)-4-quinolin-    amine43       7-chloro-N-[2-(3-methoxy-                          155-158° C.    phenyl)ethyl]-4-quinolinamine44       7-chloro-N-[2-(2,4-dichloro-                          168-170° C.    phenyl)ethyl]-4-quinolinamine45       7-chloro-N-[2-(3,5-di-                          117-120° C.    methoxyphenyl)ethyl]-4-    quinolinamine46       N-[2-(4-methoxyphenyl)-                          120-123° C.    ethyl]-6-methyl-4-quinolin-    amine47       N-[2-(4-chlorophenyl)ethyl]-                          153-155° C.    7-(trifluoromethyl)-4-quinolin-    amine48       N-[2-(3,4-dimethoxyphenyl)-                          oil    ethyl]-7-(trifluoromethyl)-4-    quinolinamine49       N-[2-(3-chlorophenoxy)ethyl]-                          161-163° C.    8-fluoro-4-quinolinamine50       7-chloro-N-[2-(4-methyl-                          155-158° C.    phenyl)ethyl]-4-quinolinamine51       8-chloro-N-[2-(4-fluoro-                          194-196° C.    phenyl)ethyl]-4-quinolinamine52       N-[2-(2,4-dichlorophenyl)-                          158-160° C.    ethyl]-8-(trifluoromethyl)-4-    quinolinamine53       N-[2-(2,4-dichlorophenyl)-                          180-182° C.    ethyl]-6-methyl-4-quinolinamine54       7-chloro-6-methoxy-2-methyl-                          180-181° C.    N-(2-phenylethyl)-4-quinolin-    amine55       N-[2-(2-methoxyphenyl)-                          127-128° C.    ethyl]-4-quinolinamine56       N-[2-(4-chlorophenyl)ethyl]-                          134-138° C.    6-fluoro-4-quinolinamine57       N-[2-(4-chlorophenyl)ethyl]-                          104-106° C.    2-methyl-6-fluoro-4-quinolin-    amine58       6-methyl-N-[2-(4-methyl-                          122-124° C.    phenyl)ethyl]-4-quinolinamine59       5,7-dichloro-N-[2-(4-chloro-                          113-115° C.    phenyl)ethyl]-4-quinolinamine60       7-chloro-N-[2-(3-phenoxy-                          128-130° C.    phenyl)ethyl]-4-quinolinamine61       8-methyl-N-[2-(4-chloro-                          118-120° C.    phenyl)ethyl] -4-quinolinamine62       8-fluoro-N-(2-cyclohexyl-2-                           74-75° C.    phenylethyl)-4-quinolinamine63       8-fluoro-N-[2-(2-phenoxyphenyl)-                          131-133° C.    ethyl]-4-quinolinamine64       7,8-dimethyl-N-[2-(2-phenoxyphenyl)-                          124-126° C.    ethyl]-4-quinolinamine65       N-[2-(2,6-difluorophenyl)-                          203-204° C.    ethyl]-8-fluoro-4-quinolin-    amine66       8-fluoro-N-[2-(3-fluoro-                          174-175° C.    phenyl)ethyl]-4-quinolinamine67       N-[2-(3,5-dimethoxyphenyl)-                          122-123° C.    ethyl]-4-quinolinamine68       8-fluoro-N-[2-(2-methoxy-                          163-164° C.    phenyl)ethyl]-4-quinolinamine69       3-chloro-N-(2-chloro-2-                          oil    phenylethyl)-4-quinolinamine70       N-(2-phenylethyl)-5,7-bis-                          oil    (trifluoromethyl)-4-quinolin-    amine71       8-fluoro-N-[2-(4-methyl-                          176-177° C.    phenyl)ethyl]-4-quinolin-    amine72       N-[2-(1,1&#39;-biphenyl)-3-ylethyl]-                          140-142° C.    8-fluoro-4-quinolinamine73       8-fluoro-4-[(2-phenylethyl)-                          107-108° C.    amino]-3-quinolinemethanol74       N-[2-(3-chlorophenyl)ethyl]-                          191-192° C.    8-fluoro-4-quinolinamine75       N-[2-(3,4-dichlorophenyl)-                          204-206° C.    ethyl]-8-fluoro-4-quinolin-    amine76       N-[2-(2,4-dichlorophenyl)-                          187-189° C.    ethyl]-8-fluoro-4-quinolin-    amine77       8-fluoro-N-(2-phenylpropyl)-                          136-137° C.    4-quinolinamine78       8-fluoro-N-[2-(4-fluoro-                          171-173° C.    phenyl)ethyl]-4-quinolinamine79       N-[2-(4-chlorophenyl)-                          126-127° C.    propyl]-8-fluoro-4-quinolin-    amine80       N-(2,2-diphenylpropyl)-8-                           56-58° C.    fluoro-4-quinolinamine81       8-fluoro-N-(2-phenylbutyl)-                          114-116° C.    4-quinolinamine82       N-[2-(2-chlorophenyl)ethyl]-                          175-177° C.    8-fluoro-4-quinolinamine83       8-fluoro-N-[2-[4-(trifluoro-                          205-206° C.    methyl)phenyl]ethyl]-4-    quinolinamine84       7-chloro-N-[2-(4-methoxy-                          122-124° C.    phenyl)ethyl]-4-quinolinamine85       8-chloro-N-[2-(4-chloro-                          185-187° C.    phenyl)ethyl]-4-quinolinamine86       N-[2-(4-chlorophenyl)ethyl]-                          192-194° C.    8-(trifluoromethyl)-4-quinolin-    amine87       8-chloro-N-[2-(4-methyl-                          184-186° C.    phenyl)ethyl]-4-quinolinamine88       N-[2-(4-chlorophenyl)ethyl]-                          177-179° C.    7,8-dimethyl-4-quinolinamine89       8-fluoro-N-[2-(4-methyl-                          153-154° C.    phenyl)ethyl]-4-quinolinamine90       8-fluoro-N-[2-(4-phenoxy-                          109-111° C.    phenyl)ethyl]-4-quinolin-    amine91       3-bromo-8-fluoro-N-(2-phenyl-                           95-97° C.    ethyl)-4-quinolinamine92       8-fluoro-N-(1-methyl-2-                          166-168° C.    phenylethyl)-4-quinolinamine93       2,8-dichloro-N-(2-phenyl-                          190-192° C.    ethyl)-4-quinolinamine94       N-[2-(4-bromophenyl)ethyl]-                          198-199° C.    8-fluoro-4-quinolinamine95       8-fluoro-N-[2-[3-(trifluoro-                          161-162° C.    methyl)phenyl]ethyl]-4-    quinolinamine96       N-[2-(4-chlorophenyl)ethyl)-                          176-177° C.    8-fluoro-4-quinolinamine97       8-fluoro-N-[2-[2-(trifluoro-                          157-158° C.    methyl)phenyl]ethyl]-4-    quinolinamine98       2-chloro-N-[2-(2,4-dichloro-                          199-200° C.    phenyl)ethyl]-8-fluoro-4-    quinolinamine99       N-(2-phenylethyl)-8-(tri-                          151-152° C.    fluoromethyl)-4-quinolin-    amine100      7-chloro-N-[2-(2-methoxy-                          140-142°    phenyl)ethyl]-4-quinolinamine101      7-chloro-N-[2-(3,4-dichloro-                          128- 130° C.    phenyl)ethyl]-4-quinolinamine102      N-[2-(4-chlorophenyl)ethyl]-                          176-178° C.    2-methyl-4-quinolinamine103      N-[2-(2-chloro-6-fluoro-                          198-201° C.    phenyl)ethyl]-8-fluoro-4-    quinolinamine104      N-[2-(2,4-dichlorophenyl)-                          175-177° C.    ethyl]-7-(trifluoromethyl)-    4-quinolinamine105      N-[2-(4-chlorophenyl)ethyl]-                          oil    N-ethyl-8-fluoro-4-quinolin-    amine106      7-chloro-N-(4-fluorophenyl)-                           83-85° C.    N-methyl-4-quinolinamine107      7-chloro-N-[2-[3-(trifluoro-                          184-186° C.    methyl)phenyl]ethyl]-4-    quinolinamine108      N-[2-(3-bromophenyl)ethyl]-                          206-208° C.    8-fluoro-4-quinolinamine109      N-[2-(4-chlorophenyl)ethyl]-5,8-                          oil    dimethyl-4-quinolinamine110      N(4)-[2-(4-chlorophenyl)ethyl]-                          oil    4,8-quinolinamine111      N-[2-[4-( .sub.- t-butyl)phenyl]ethyl]-                          198-200° C.    8-fluoro-4-quinolinamine112      N-[2-(2,3,4,5,6-tetramethyl-                          204-207° C.    phenyl)ethyl]-8-fluoro-4-    quinolinamine113      N-[2-(1,1-biphenyl)-4-yl-                          178-180° C.    ethyl]-8-fluoro-4-quinolin-    amine114      N-[2-[4-( .sub.- i-propyl)phenyl]ethyl]-                          157-159° C.    8-fluoro-4-quinolinamine115      N-[2-(2-chlorophenyl)ethyl]-                          205-207° C.    8-chloro-4-quinolinamine116      2-chloro-8-fluoro-N-(2-                          158-159° C.    phenylethyl)-4-quinolinamine117      8-fluoro-N-[2-(4-nitro-                          234-236° C.    phenyl)ethyl]-4-quinolin-    amine118      N-[2-(2,6-dichlorophenyl)-                          222-224° C.    ethyl]-8-fluoro-4-quinolin-    amine119      N-[2-(3,5-dimethoxyphenyl)-                          131-132° C.    ethyl]-8-fluoro-4-quinolin-    amine120      N-(2-phenylcyclopropyl)-4-                          147-148° C.    quinolinamine121      N-[2-(4-chlorophenyl)ethyl]-N-                           87-88° C.    (6-fluoro-4-quinolinyl)acetamide122      N-[2-(4-methylphenyl)ethyl]-N-                           97-98° C.    (6-methyl-4-quinolinyl)acetamide123      8-fluoro-N-(2-phenylcyclopropyl)-4-                          204-205° C.    quinolinamine124      N-[2-(4-chlorophenyl)ethyl]-N-(7-                          oil    chloro-4-quinolinyl)acetamide125      N-(7-chloro-4-quinolinyl)-N-[2-(4-                          oil    methoxyphenyl)ethyl]acetamide126      N-(7-chloro-4-quinolinyl)-N-[2-[3-                          oil    (trifluoromethyl)phenyl]ethyl]-    acetamide127      N-[2-(2,4-dichlorophenyl)ethyl]-N-                          oil    [7-(trifluoromethyl)-4-quinolinyl]-    acetamide128      N-[4-( .sub.- t-butyl)phenyl]ethyl-N-(8-                          126-128° C.    fluoro-4-quinolinyl)acetamide129      N-[2-[4-( .sub.- i-propyl)phenyl]ethyl]-                           82-84° C.    N-(8-fluoro-4-quinolinyl)acetamide130      N-[2-(1,1&#39;-biphenyl)-4-ylethyl]-N-                          oil    (8-fluoro-4-quinolinyl)acetamide131      N-[2-(pentamethylphenyl)ethyl]-N-                          oil    (8-fluoro-4-quinolinyl)acetamide132      N-[2-(2-chlorophenyl)ethyl]-N-(8-                          104-106° C.    chloro-4-quinolinyl)acetamide133      N-[2-(4-methoxyphenyl)ethyl]-7,8-                          183-185° C.    dimethyl-4-quinolinamine______________________________________ *not a compound claimed per se, but one used in the claimed compositions and methods. 
    
     
                       TABLE 2______________________________________N-(3-phenylpropyl)-4-quinolinaminesEXAMPLENUMBER   COMPOUND              M.P.______________________________________134      7-chloro-N-[3-(1,1&#39;-biphenyl)-4-                          122-124° C.    ylpropyl]-4-quinolinamine135      N-[3-(4-chlorophenyl)propyl]-8-                          134-136° C.    fluoro-4-quinolinamine136      N-[3-(4-chlorophenyl)propyl]-7-                          177-179° C.    chloro-4-quinolinamine137      N-[3-(1,1&#39;-biphenyl)-4-ylpropyl]-                          124-127° C.    8-fluoro-4-quinolinamine138      8-fluoro-N-(1-methyl-3-phenylpropyl)-                          164-166° C.    4-quinolinamine139      N-(3-phenylpropyl)-4-quinolinamine                           96-97° C.______________________________________ 
    
     
                       TABLE 3______________________________________N-(4-phenylbutyl)-4-quinolinaminesEXAMPLENUMBER   COMPOUND             M.P.______________________________________140      8-fluoro-N-[4-(4-chlorophenyl)-                         110-112° C.    butyl]-4-quinolinamine141      N-[4-(4-chlorophenyl)butyl]-N-(8-                         oil    fluoro-4-quinolinyl)acetamide______________________________________ 
    
     
                       TABLE 4______________________________________N-Arylalkyl-4-quinolinaminesEXAMPLENUMBER   COMPOUND              M.P.______________________________________142      N-[2-(1-cyclohexenyl)ethyl]-5,8-                          78-81° C.    dimethyl-4-quinolinamine143      N-[2-(1-cyclohexenyl)ethyl]-8-                          153-155° C.    fluoro-4-quinolinamine144      N-[2-(1-cyclohexenyl)ethyl]-6,8-                          114-116° C.    dimethyl-4-quinolinamine145      N-[2-(1-cyclohexenyl)ethyl]-6-                          135-137° C.    ethyl-4-quinolinamine146      N-[2-(1-cyclohexenyl)ethyl]-N-                          66-68° C.    (6-fluoro-4-quinolinyl)acetamide147      N-[2-(2-thienyl)ethyl]-4-quinolin-                          153-154° C.    amine148      N-[2-(3-thienyl)ethyl]-4-quinolin-                          156-157° C.    amine149      6,8-difluoro-N-[2-(2-thienyl)ethyl]-                          175-176° C.    4-quinolinamine150      6,8-difluoro-N-[2-(3-thienyl)ethyl]-                          191-192° C.    4-quinolinamine151      N-[2-(1-naphthyl)ethyl]-4-                          149-150° C.    quinolinamine152      N-[2-(2-naphthyl)ethyl]-4-                          160-161° C.    quinolinamine153      N-[2-(2-thienyl)ethyl]-7-(trifluoro-                          131-132° C.    methyl)-4-quinolinamine154      8-fluoro-N-[2-(4-phenyl-2-thiazolyl)-                          134-135° C.    ethyl]-4-quinolinamine155      8-chloro-N-[2-(1-naphthyl)ethyl]-                          205-206° C.    4-quinolinamine156      8-chloro-N-[2-(2-naphthyl)ethyl]-                          206-208° C.    4-quinolinamine157      α-[[(8-fluoro-4-quinolinyl)amino]-                          182-185° C.    methyl]-2-naphthalenemethanol158      8-fluoro-N-[2-(1-naphthyl)ethyl]-                          152-153° C.    4-quinolinamine159      8-fluoro-N-[2-(2-naphthyl)ethyl]-                          173-174° C.    4-quinolinamine160      N-[2-(1-cyclohexenyl)ethyl]-N-(5,8-                          oil    dimethyl-4-quinolinyl)acetamide161      N-(2-cyclohexylethyl)-N-(8-fluoro-                          oil    4-quinolinyl)acetamide162      8-fluoro-N-[2-(5-methyl-2-thienyl)-                          161-163° C.    ethyl]-4-quinolinamine163      N-[2-(5-chloro-2-thienyl)ethyl]-8-                          167-168° C.    fluoro-4-quinolinamine164      8-fluoro-N-[2-(1H-imidazol-4-yl)-                          230° C.    ethyl]-4-quinolinamine165      7-chloro-N-[2-(1-cyclohexenyl)-                          161-163° C.    ethyl]-4-quinolinamine166      7-chloro-N-[2-(2-naphthyl)-                          156-158° C.    ethyl]-4-quinolinamine167      N-[2-(1-cyclohexenyl)ethyl]-7-                          158-160° C.    (trifluoromethyl)-4-quinolinamine168      N-[2-(1-cyclohexenyl)ethyl]-6-                          129-131° C.    fluoro-4-quinolinamine169      N-[2-(2-naphthyl)ethyl]-7-(tri-                          127-130° C.    fluoromethyl)-4-quinolinamine170      8-fluoro-N-[1-methyl-2-(2-thienyl)-                          217-219° C.    ethyl]-4-quinolinamine171      N-[1-methyl-2-(2-thienyl)ethyl]-                          167-168° C.    4-quinolinamine172      8-chloro-N-[2-(2-thienyl)ethyl]-4-                          161-162° C.    quinolinamine173      8-fluoro-N-[2-(2-thienyl)ethyl]-4-                          157-158° C.    quinolinamine174      N-[2-(2,3-dihydro-1,4-benzodioxin-                          170-171° C.    2-yl)ethyl]-8-fluoro-4-quinolinamine175      8-fluoro-N-[2-(3-thienyl)ethyl]-4-                          163-164° C.    quinolanamine176      8-fluoro-N-[2-(1H-indol-3-yl)ethyl]-                          205-206° C.    4-quinolinamine177      N-(2-cyclohexylethyl)-8-fluoro-4-                          145-147° C.    quinolinamine178      N-(2-cyclohexylethyl)-6,8-dimethyl-                          155-157° C.    4-quinolinamine179      N-[2-(1-cyclohexenyl)ethyl]-N-(6,8-                          oil    dimethyl-4-quinolinyl)acetamide180      8-fluoro-N-[2-(2-pyridinyl)ethyl]-                          143-144° C.    4-quinolinamine______________________________________ 
    
     
                       TABLE 5______________________________________Bis[2-phenylethyl]quinolinediaminesEXAM-PLENUMBER  COMPOUND               M.P.______________________________________181     N,N&#39;-bis(2-phenylethyl)-2,4-                          70-71° C.   quinolinediamine182     N,N&#39;-(2,4-quinolinediyl)bis[N-[2-(4-                          oil   chlorophenyl)ethyl]acetamide]183     8-fluoro-N,N&#39;-bis(2-phenylethyl)-2,4-                          oil   quinolinediamine184     N,N&#39;-bis(2-phenylpropyl)-2,4-quinoline-                          oil   diamine185     N,N&#39;-bis[2-(4-chlorophenyl)ethyl]-                          135-137° C.   4,6-quinolinediamine186     N,N&#39;-bis[2-(4-chlorophenyl)ethyl]-4,7-                          55-60° C.   quinolinediamine187     N,N&#39;-bis[2-(4-methoxyphenyl)ethyl]-                          140-150° C.   4,7-quinolinediamine188     N,N&#39;-bis[2-(4-chlorophenyl)ethyl]-8-                          oil   fluoro-2,4-quinolinediamine189     N,N&#39;-bis(2-phenylethyl)-4,8-quinoline-                          83-84° C.   diamine190     N,N&#39;-bis[2-(2,4-dichlorophenyl)ethyl]-                          116-117° C.   8-fluoro-2,4-quinolinediamine191     N,N&#39;-(4,7-quinolinediyl)bis[N-[2-(4-                          oil   chlorophenyl)ethyl]acetamide]______________________________________ 
    
     
                       TABLE 6______________________________________Bis[2-arylethyl]quinolinediaminesEXAMPLENUMBER   COMPOUND              M.P.______________________________________192      N,N&#39;-bis[2-(1-cyclohexen-yl)ethyl]-                          129-131° C.    4,6-quinolinediamine______________________________________ 
    
     
                       TABLE 7______________________________________4-(2-phenylethoxy)quinolinesEXAM-PLENUMBER  COMPOUND               M.P.______________________________________193     2-chloro-8-fluoro-4-[2-(4-methyl-                          76-77° C.   phenyl)ethoxy]quinoline194     5,7-dichloro-4-[2-(1,1&#39;-biphenyl)-                          100-102° C.   4-ylethoxy]quinoline195     4-[2-(3-methoxyphenyl)ethoxy]-8-                          90-91° C.   fluoroquinoline196     8-fluoro-4-[2-(4-methoxyphenyl)-                          70-71° C.   ethoxy]quinoline197     8-fluoro-4-[2-(3-phenoxyphenyl)-                          73-75° C.   ethoxy]quinoline198     8-bromo-4-[2-(4-( .sub.- t-butyl)phenyl)-                          115-118° C.   ethoxy]quinoline199     4-[2-(3,4-dimethoxyphenyl)ethoxy]-8-                          113-114° C.   fluoroquinoline200     8-fluoro-N-[2-(1,1&#39;-biphenyl)-4-yl-                          141-142° C.   ethoxy]quinoline201     4-[2-(3-chlorophenyl)ethoxy]-8-fluoro-                          76-77° C.   quinoline202     7-chloro-4-(2-phenylethoxy)quinoline                          oil203     8-fluoro-4-[2-(3-(trifluoromethyl)-                          98-99° C.   phenyl)ethoxy]quinoline204     7-chloro-4-[2-(4-methylphenyl)ethoxy]-                          87-88° C.   quinoline205     8-fluoro-4-[2-(2-methylphenyl)ethoxy]-                          72° C.   quinoline206     8-fluoro-4-[2-(2-(trifluoromethyl)-                          60° C.   phenyl)ethoxy]quinoline207     8-chloro-4-(2-phenylethoxy)quinoline                          73-74° C.208     4-(2-phenylethoxy)quinoline                          oil209     4-[2-(4-chlorophenyl)ethoxy]-8-fluoro-                          138-140° C.   quinoline210     4-[2-(4-methylphenyl)ethoxy]quinoline                          59-60° C.211     4-[2-(4-chlorophenyl)ethoxy]quinoline                          106-107° C.212     8-fluoro-4-[2-(4-methylphenyl)ethoxy]-                          89-90°  C.   quinoline213     4-(1-methyl-2-phenylethoxy)quinoline                          oil214     8-fluoro-4-[1-(phenylmethyl)ethoxy]-                          oil   quinoline215     8-bromo-4-[2-(4-chlorophenyl)ethoxy]-                          112-114° C.   quinoline216     8-chloro-4-[2-(2-chlorophenyl)ethoxy]-                          90-92° C.   quinoline217     8-fluoro-4-[2-(2-(1-methylethyl)phenyl)-                          oil   ethoxy]quinoline218     8-fluoro-4-[2-(3-(phenylthio)phenyl)-                          oil   ethoxy]quinoline219     8-fluoro-4-(2-phenylethoxy)quinoline                          63-65° C.220     4-(2-phenylpropoxy)-8-fluoroquinoline                          oil221     4-[2-[4-( .sub.- t-butyl)phenyl]ethoxy]-                          81-82° C.   8-fluoroquinoline222     8-fluoro-4-[2-(4-fluorophenyl)-                          126-127° C.   ethoxy]quinoline223     4-[2-(4-bromophenyl)ethoxy]-8-                          130° C.   fluoroquinoline224     8-fluoro-4-[2-(3-methylphenyl)ethoxy]-                          92° C.   quinoline225     8-fluoro-4-[2-(2-fluorophenyl)ethoxy]-                          75° C.   quinoline226     7-chloro-4-[2-(4-chlorophenyl)ethoxy]-                          96-97° C.   quinoline227     8-fluoro-4-[2-(2,4,6-trimethylphenyl)-   ethoxy]quinoline228     8-fluoro-4-[2-(2-methoxyphenyl)ethoxy]-                          74-75° C.   quinoline229     4-[2-(2-methoxyphenyl)ethoxy]quinoline                          oil230     7-chloro-4-[2-(1,1&#39;-biphenyl)-4-yl-                          95-96° C.   ethoxy]quinoline231     7-chloro-4-[2-(4-( .sub.- t-butyl)phenyl)-                          123-124° C.   ethoxy]quinoline232     4-[2-(4-( .sub.- t-butyl)phenyl)ethoxy]-7-                          98-99° C.   fluoroquinoline233     4-[2-(1,1&#39;-biphenyl)-4-ylethoxy]-7-                          73-75° C.   fluoroquinoline234     4-[2-(4-chlorophenyl)ethoxy] -7-fluoro-                          81-82° C.   quinoline235     7-fluoro-4-[2-(4-methylphenyl)ethoxy]-                          85-86° C.   quinoline236     7-chloro-4-[2-(4-fluorophenyl)ethoxy]-                          80° C.   quinoline237     8-fluoro-4-[2-(1,1&#39;-biphenyl)-2-yl-                          55-60° C.   ethoxy]quinoline238     8-fluoro-4-[2-(4-( .sub.- i-propyl)phenyl)-                          59-60° C.   ethoxy]quinoline239     4-(2-phenylethoxy)-7-(trifluoro-                          55-57° C.   methyl)quinoline240     8-chloro-4-[2-(4-fluorophenyl)-                          125-127° C.   ethoxy]quinoline______________________________________ 
    
     
                       TABLE 8______________________________________4-(3-phenylpropoxy)quinolinesEXAMPLENUMBER   COMPOUND              M.P.______________________________________241      8-fluoro-4-[3-[4-( .sub.- t-butyl)phenyl]-                          103-105° C.    propoxy]quinoline242      8-chloro-4-[3-(4-chlorophenyl)-                          117-119° C.    propoxy]quinoline243      8-fluoro-4-[(3-phenyl-2-propenyl)-                          128-130° C.    oxy]quinoline______________________________________ 
    
     
                       TABLE 9______________________________________4-(2-Arylethoxy)quinolinesEXAMPLENUMBER   COMPOUND              M.P.______________________________________244      8-fluoro-4-[2-(1-naphthyl)-                          121-122° C.    ethoxy]quinoline245      4-[2-(2-thienyl)ethoxy]-                          oil    quinoline246      8-fluoro-4-[2-(2-thienyl)-                          77-79° C.    ethoxy]quinoline247      8-fluoro-4-[2-(2-naphthyl)ethoxy]-                          123-124° C.    quinoline248      5-chloro-4-(2-cyclohexylethoxy)-2,8-                          100-102° C.    dimethylquinoline249      6-fluoro-4-(2-cyclohexylethoxy)-2-                          113-115° C.    methylquinoline______________________________________ 
    
     
                       TABLE 10______________________________________Bis(2-phenylethoxy)quinolinesEXAMPLENUMBER   COMPOUND              M.P.______________________________________250      8-fluoro-2,4-bis[2-(4-methyl-                          125-126° C.    phenyl)ethoxy]quinoline251      4,8-bis[2-(4-methylphenyl)ethoxy]-                          142-143° C.    quinoline______________________________________ 
    
     
                       TABLE 11______________________________________4-(3-Arylpropyl)quinolinesEXAMPLENUMBER   COMPOUND               M.P.______________________________________252      4-(3-phenylpropyl)quinoline253      8-fluoro-4-(3-phenylpropyl)quinoline                           43-45° C.254      4-(3-phenylpropyl)-7-(trifluoro-                           oil    methyl)quinoline255      8-chloro-4-(3-phenylpropyl)quinoline                           70-71° C.256      8-fluoro-4-[3-(4-( .sub.- i-propyl)phenyl)-                           oil    propyl]quinoline257      4-[3-(1,1&#39;-biphenyl)-4-ylpropyl]-8-                           oil    fluoroquinoline258      8-fluoro-4-[3-(4-methylphenyl)propyl)]-                           oil    quinoline259      8-fluoro-4-[3-[3-(trifluoromethyl)-                           65-66° C.    phenyl]propyl]quinoline260      4-[3-[4-( .sub.- t-butyl)phenyl]propyl]-8-                           oil    fluoroquinoline261      4-[3-(4-chlorophenyl)propyl]-8-fluoro-                           97° C.    quinoline______________________________________ 
    
     
                       TABLE 12______________________________________Additional CompoundsEXAM-PLENUMBER  COMPOUND               M.P.______________________________________262     4-[2-[4-( .sub.- t-butyl)phenyl]ethoxy]-                          67-69° C.   quinoline263     8-fluoro-4-[2-(1,1&#39;-biphenyl)-4-yl-                          97-99° C.   ethoxy]quinoline264     8-fluoro-4-[(2-phenylethyl)sulfinyl]-                          NA   quinoline265     8-fluoro-4-[2-[4-(2-hydroxyethyl)-                          NA   phenyl]ethoxy]quinoline266     8-fluoro-4-[3-methoxybutoxy]-                          oil   quinoline267     8-fluoro-4-(4-pentenoxy)quinoline                          75-78° C.268     8-fluoro-N-(4-phenylbutyl)-4-                          104-106° C.   quinolinamine269     4-[2-(2-chlorophenyl)ethoxy]-8-                          78-80° C.   fluoroquinoline270     4-[2-[1,1&#39;-biphenyl]-4-ylbutoxy]-8-                          oil   fluoroquinoline271     N-[3-[4-( .sub.- t-butyl)phenyl]propyl]-8-                          oil   fluoro-4-quinolinamine272     8-fluoro-4-(4-phenoxybutoxy)quinoline                          87-89° C.273     N-[2-(4-acetoxyphenyl)ethyl]-N-(8-                          oil   fluoro-4-quinolinyl)acetamide274     8-fluoro-4-(3,5,5-trimethylhexyloxy)-                          oil   quinoline275     8-fluoro-4-[2-(2,4-difluorophenyl)-                          98-100° C.   ethoxy]quinoline276     7-chloro-4-[2-(2,4-difluorophenyl)-                          103-105° C.   ethoxy]quinoline277     5,7-dichloro-4-[2-(4-ethoxyphenyl)-                          104-105° C.   ethoxy]quinoline278     4-[2-(4-butoxyphenyl)ethoxy]-8-                          80-82° C.   fluoroquinoline279     6-ethoxy-2-methyl-4-[3-(phenyl-                          38-40° C.   methoxy)propoxy]quinoline280     8-chloro-N-[2-(3-phenoxyphenyl)-                          145-147° C.   ethyl]-4-quinolinamine281     8-chloro-N-(4-phenylbutyl)-4-quino-                          134-136° C.   linamine282     8-fluoro-4-[3-(4-phenoxyphenyl)pro-                          94-96° C.   poxy]quinoline283     7-chloro-N-[2-(4-chlorophenyl)-                          145-147° C.   propyl]-4-quinolinamine284     4-[(4,5-dibromopentyl)oxy]-8-fluoro-                          70-73° C.   quinoline285     8-fluoro-4-[(8-phenoxyoctyl)oxy]-                          80-81° C.   quinoline286     6-chloro-2-methyl-4-[2-[4-( .sub.- t-butyl)-                          83-86° C.   phenyl]ethoxy]quinoline287     8-fluoro-4-[(6-phenoxyhexyl)oxy]-                          NA   quinoline288     8-chloro-N-(2-methyl-2-phenylpropyl)-                          137-139° C.   4-quinolinamine289     8-fluoro-N-(2-methyl-2-phenylpropyl)-                          136-138° C.   4-quinolinamine290     6-methoxy-2-methyl-N-[2-(3-phenoxy-                          NA   phenyl)ethyl]-4-quinolinamine291     8-fluoro-N-[2-[4-(phenylmethoxy)-                          157-159° C.   phenyl]ethyl]-4-quinolinamine292     7-fluoro-4-[2-(4-bromophenoxy)-                          127-129° C.   ethoxy]quinoline293     N-[2-(4-hydroxyphenyl)ethyl]-8-                          249-251° C.   fluoro-4-quinoline294     8-fluoro-4-[3-[3-(trifluoromethyl)-                          67-69° C.   phenyl]propoxy]quinoline295     8-fluoro-4-(2-phenylcyclohexyloxy)-                          NA   quinoline296     8-chloro-N-[2-(2,4-difluorophenyl)-                          206-208° C.   ethyl]-4-quinolinamine297     8-fluoro-4-[2-[4-(1,1,2,2-tetra-                          70-72° C.   fluoroethoxy)phenyl]ethoxy]quinoline298     N-[2-[3,4-bis(phenylmethoxy)-                          137-139° C.   phenyl]ethyl]-8-fluoro-4-quinolinamine299     4-[2-(6-chloro-1,3-benzodioxol-5-yl)-                          143-145° C.   ethoxy]-8-fluoroquinoline300     8-fluoro-N-[2-(4-ethoxyphenyl)ethyl]-                          179-181° C.   4-quinolinamine301     N-[2-(4-ethoxyphenyl)ethyl]-4-                          125-126° C.   quinolinamine302     8-fluoro-4-[3-(4-ethoxyphenyl)propyl]-                          oil   quinoline303     4-[3-(4-ethoxyphenyl)propyl]quinoline                          oil304     8-fluoro-4-[3-(4-methoxyphenyl)-                          oil   propyl]quinoline305     8-fluoro-4-(2,2-dimethylbutoxy)-                          oil   quinoline306     8-fluoro-N-[2-[4-(butoxy)phenyl]-                          118-120° C.   ethyl]-4-quinolinamine307     7-[(8-fluoro-4-quinolinyl)oxy]-                          94-96° C.   heptanenitrile308     8-fluoro-4-[2-(3,4-difluorophenyl)-                          87-89° C.   ethoxy]quinoline309     8-fluoro-4-[2-(1,3-benzodioxol-5-                          103-105° C.   yl)ethoxy]quinoline310     4-[2-(2,6-dichlorophenyl)ethoxy]-                          128-129° C.   8-fluoroquinoline311     8-chloro-4-[2-(2-chloro-4-fluoro-                          104-106° C.   phenyl)ethoxy]quinoline312     8-fluoro-N-[2-(3-methoxyphenyl)-                          153-155° C.   ethyl]-4-quinolinamine313     8-fluoro-N-[2-(4-ethylphenyl)-                          162-164° C.   ethyl]-4-quinolinamine314     8-fluoro-4-[2-[4-(heptyloxy)phenyl]-                          45-47° C.   ethoxy]quinoline315     (E)-8-fluoro-4-[(2-phenylethenyl)-                          99-101° C.   oxy]quinoline316     (Z)-8-fluoro-4-[(2-phenylethenyl)-                          95-97° C.   oxy]quinoline317     8-fluoro-N-[2-[4-(propoxy)phenyl]-                          140-142° C.   ethyl]-4-quinolinamine318     8-chloro-4-[2-(3,4-difluorophenyl)-                          84-86° C.   ethoxy]quinoline319     4-[3-[4-( .sub.- i-propyl)phenyl]propyl]-                          oil   quinoline320     7-chloro-4-[2-(1,3-benzodioxol-5-yl)-                          75-77° C.   ethoxy]quinoline321     8-fluoro-4-[2-(4-methoxyphenoxy)-                          107-109°  C.   ethoxy]quinoline322     8-fluoro-4-[2-[4-(3-methylphenoxy)-                          98-100° C.   phenyl]ethoxy]quinoline323     8-chloro-4-[2-(2,4-difluorophenyl)-                          118-120° C.   ethoxy]quinoline324     N-[2-(5-bromo-2-methoxyphenyl)ethyl]-                          176-178° C.   8-fluoro-4-quinolinamine325     8-fluoro-4-[2-(4-propoxyphenyl)-                          108-110° C.   ethoxy]quinoline326     8-fluoro-4-(2-phenoxyethoxy)quinoline                          118-120° C.327     8-fluoro-N-[4-[4-(trifluoromethyl)-                          110-112° C.   phenyl]butyl]-4-quinolinamine328     8-fluoro-N-[2-[4-(1,1,2,2-tetra-                          168-170° C.   fluoroethoxy)phenyl]ethyl]-4-quinolin-   amine______________________________________ 
    
     The procedures described in the following detailed Examples are representative of the procedures used to prepare the compounds of the other Examples. 
     EXAMPLE 4 
     N-Ethyl-N-(2-phenylethyl)-4-quinolinamine 
     To a suspension of 0.59 g of lithium aluminum hydride in 100 mL of dry ether was added, dropwise, a solution of 2.3 g of N-(2-phenylethyl)-N-(4-quinolinyl)acetamide dissolved in 50 mL of dry ether. The mixture was heated to reflux for seven hours. Excess lithium aluminum hydride was then destroyed by adding 100 mL of water to the mixture. The solvent was then removed, and the residue was dissolved in chloroform. After washing with water, the mixture was then dried and concentrated. Using HPLC (silica gel, CH 2  Cl 2  →EtOAc), 0.80 g of the title product was isolated. Yield 36.7%. M.P. oil. 
     EXAMPLE 10 
     N-[2-(4-Chlorophenyl)ethyl]-N-[8-fluoro-4 quinolinyl]acetamide 
     A mixture of 2.0 g of N-[2-(4-chlorophenyl)ethyl]-8-fluoro-4-quinolinamine and 5.0 mL of acetic anhydride was refluxed overnight. The mixture was then cooled, and solvents were removed by reducing pressure. The residue was washed with water and then dried. The resulting oil was passed over a silica gel column with ethyl acetate, and the front running spot was collected, producing 0.8 g of the title product as a thick oil. 
     EXAMPLE 25 
     2-Chloro-N-(2-phenylethyl)-4-quinolinamine 
     To 0.6 g of 2-hydroxy-N-(2-phenylethyl)-4-quinolinamine was added 15 mL of POCl 3 . The mixture was heated to reflux overnight, then cooled and concentrated to dryness. A mixture of ammonium hydroxide in water was added, then the product was extracted into CH 2  Cl 2 . This solution was concentrated to dryness, and the product was recrystallized from pentane/CH 2  Cl 2 , giving 0.55 g of the title product. Yield 85.9%. M.P. 132°-133° C. 
     EXAMPLE 69 
     3-Chloro-N-(2-chloro-2-phenylethyl)-4-quinolinamine 
     A mixture of 4.1 g of 1-phenyl-2-(4-quinolinylamino)ethanol, 100 mL of POCla and 6.5 g of PCls was heated to reflux for 18 hours, then cooled and concentrated to dryness. An ice/water mixture was added, then the product was extracted into CH 2  Cl 2 . This solution was concentrated to dryness, and the residue was purified by HPLC (silica gel column eluted with pentane/CH 2  Cl 2  (50:50)). Fractions containing the product were combined and concentrated to dryness producing 0.433 g of the title product. Yield 8.7%. M.P. oil. 
     EXAMPLE 97 
     8-Fluoro-N-[2-(2-trifluoromethyl)phenyl]-4-quinolinamine 
     To 2.0 g of 4-chloro-8-fluoroquinoline was added 4.1 g of 2-[2-(trifluoromethyl)phenyl]ethylamine. The mixture was stirred and heated to 160°-165° C. under nitrogen for two hours, then cooled, and 200 mL of a 50:50 mixture of ammonium hydroxide and water was added. The product was extracted into CH 2  Cl 2 , which was concentrated to dryness. Recrystallization from a pentane/CH 2  Cl 2  mixture yielded 1.5 g of the title product. Yield 41.6%. 
     EXAMPLE 154 
     8-Fluoro-N-[2-(4-phenyl-2-thiazolyl)ethyl]-4-quinolinamine 
     To 1.0 g of 4-chloro-8-fluoroquinoline was added 2.6 g of 2-β-aminoethyl-4-phenylthiazole monohydrochloride. The mixture was stirred under nitrogen and heated to 170°-175° C. for one hour. The mixture was then cooled and 250 mL of a 50:50 mixture of ammonium hydroxide and water was added. The product was extracted into CH 2  Cl 2 , which was then concentrated to dryness. Recrystallizing from pentane/CH 2  Cl 2  gave 0.410 g of the title product. Yield 21.6%. M.P. 134°-135° C. 
     EXAMPLE 159 
     8-Fluoro-N-[2-(2-naphthyl)ethyl]-4-quinolinamine 
     A mixture of 2.0 g of 4-chloro-8-fluoroquinoline and 3.8 g of 2-(2-naphthyl)ethyl amine was heated under nitrogen to 160°-165° C. for one hour. Then 200 mL of a 50:50 mixture of ammonium hydroxide in water was added. The product was extracted from the mixture into CH 2  Cl 2 , which was then concentrated to dryness. The residue was recrystallized from pentane/ethyl acetate to give 1.4 g of the title product. Yield 41.2%. M.P. 173°-174° C. 
     EXAMPLE 173 
     8-Fluoro-N-[2-(2-thienyl)ethyl]-4-quinolinamine 
     A mixture of 2.0 g of 4-chloro-8-fluoroquinoline and 2.8 g of 2-(2-thienyl)ethyl amine was heated under nitrogen to 160°-165° C. for two hours, then cooled and combined with 200 mL of a 50:50 mixture of ammonium hydroxide and water. The product was extracted into CH 2  Cl 2 , which was then concentrated to dryness. The residue was recrystallized from pentane/CH 2  Cl 2  to give 1.0 g of the title product. Yield 34.5%. M.P. 157°-158° C. 
     EXAMPLE 181 
     Bis[2-phenylethyl]-2,4-quinolinediamine 
     To 2.0 g of 2,4-dichloroquinoline was added 4.8 g of 2-phenylethylamine, and the mixture was heated to 150°-160° C. under nitrogen for 18 hours. The mixture was then cooled and a solution of ammonium hydroxide and water was added. The product was extracted into CH 2  Cl 2 , which was then concentrated to dryness, giving an oil. To the oil, 100 mL of pentane and CH 2  Cl 2  was added and the oil went into solution. This solution was cooled, and the title product crystallized. Yield 44.4%. M.P. 70°-71° C. 
     EXAMPLE 186 
     N,N&#39;-Bis[2-(4-chlorophenyl)ethyl]-2,7-quinolinediamine 
     A mixture of 2.0 g of 4-chloro-7-fluoroquinoline and 3.5 g of 2-(4-chlorophenyl)ethyl amine was heated neat until fuming began. The mixture was then cooled. The product was extracted into a CHClz/ammonium hydroxide solution, which was then washed with water. Solvent was removed by reducing pressure. The residue was placed on a silica gel column with acetone, then flushed with ethanol. Solvent was removed by reducing pressure, giving the title product as a yellow-brown foam. Yield 1.1 g. M.P. 55°-60° C. 
     EXAMPLE 209 
     4-[2-(4-Chlorophenyl)ethoxy]-8-fluoroquinoline 
     To 1.2 g of sodium hydride in 50 mL of DMF was added 3.9 g of 2-(4-chlorophenyl)ethyl alcohol. The mixture was stirred at room temperature for one hour, then 4.5 g of 4-chloro-8-fluoroquinoline in 10 mL of DMF was added, the mixture was heated to reflux for two hours. Then the mixture was allowed to cool to room temperature while it was stirred for four hours, after which it was poured into an ice/water mixture. The mixture was filtered, and the filter cake was washed with H 2  O. Recrystallization from pentane/ethyl acetate gave 0.840 g of the title product. Yield 11.2%. M.P. 139°-140° C. 
     EXAMPLE 221 
     4-[2-[4-(t-Butyl)phenyl]ethoxy]-8-fluoroquinoline 
     To a mixture of 1.1 g of sodium hydride in 50 mL of DMF was added 4.0 g of 2-[4-(1,1-dimethylethyl)phenyl]ethyl alcohol, and the mixture was stirred for one hour at room temperature. Then 4.0 g of 4-chloro-8fluoroquinoline in 20 mL of DMF were added, and the mixture was stirred at room temperature overnight. Then the mixture was poured into an ice/water mixture, and the solid was collected and recrystallized from ethyl acetate/pentane to give 2.3 g of the title product. Yield 32.4%. M.P. 81°-82° C. 
     EXAMPLE 238 
     8-Fluoro-4-[2-[4-(i-propyl)phenyl]ethoxyquinoline 
     To a suspension of 0.96 g of sodium hydride in 10 mL of dry DMF was added 3.6 g of 4-chloro-8-fluoroquinoline. The mixture was cooled in an ice/water bath, and 3.3 g of 2-[4-(1-methylethyl)phenyl]ethyl alcohol was added. The mixture was stirred overnight, then diluted with ice and water. The pH was adjusted to 7, then the product was extracted into CH 2  Cl 2 . The CH 2  Cl 2  layer was separated, filtered, and evaporated in vacuo. An azeotrope with xylene was formed to facilitate removal of residual DMF. The residue was chromatographically purified on a silica gel column, eluting with CH 2  Cl 2 , →5% EtOAc/CH 2  Cl 2  →10% EtOAc/CH 2  Cl 2 . The fractions containing product were combined and evaporated to give an oil, which crystallized on adding ether. Recrystallization yielded 2.5 g of title product. M.P. 56°-60° C. 
     EXAMPLES 212 and 251 
     8-fluoro-4-[2-(4-methylphenyl)ethoxy]quinoline, 
     4,8-Bis[2-(4-methylphenyl)ethoxy]quinoline 
     To a solution of 1.2 g of sodium hydride in 50 ml of DMF was added 3.4 g of 2-(4-methylphenyl)ethanol, and the mixture was stirred for one hour at room temperature. Then 4.5 g of 4-chloro-8-fluoroquinoline were added, the mixture was heated to reflux for five hours, and then cooled to room temperature, and poured into a mixture of ice in water. The solid phase was collected and dried. TLC showed three products. These were separated by HPLC (silica gel, 70% pentane/30% EtOAc) giving 1.84 g of 8-fluoro-4-[2-(4-methylphenyl)ethoxy]quinoline (Yield: 26.3%; M.P. 89°-90° C.) 0.610 g of 4-chloro-8-[2-(4-methylphenyl)ethoxy]quinoline (Yield: 8.7%; M.P. 74°-75° C.); and 0.450 g of 4,8-bis[2-(4-methylphenyl)ethoxy]quinoline (Yield: 6.4%; M.P. 142°-143° C). 
     EXAMPLE 261 
     4-[3-(4-chlorophenyl)propyl]-8-fluoroquinoline 
     A mixture of 3.63 g of 4-chloroquinoline and 5.3 g of 5-[2-(4-chlorophenyl)ethyl]barbituric acid was heated to 150° C. for 11/4 hours, to form 5-[2-(4-chlorophenyl)ethyl]-5-(4-quinolinyl)barbituric acid. This compound was hydrolyzed, without isolation, by adding 4 g of NaOH in 40 ml of water and refluxing for four hours. The mixture was cooled, acidified with HCl and refluxed for several hours, cooled, and neutralized with dilute NaOH. The desired product was extracted into CH 2  Cl 2 , which was then filtered through phase separating paper and evaporated to dryness. The residue was absorbed onto silica gel and chromatographed over silica gel using CH 2  Cl 2 . Fractions containing product were combined to give 2.69 g of crystalline material. This was recrystallized from a petroleum ether/CH 2  Cl 2  mixture to give 2.35 g of the title product. Yield: 39%. M.P. 97° C. 
     Utility 
     Plant Pathology 
     The compounds of the present invention have been found to control fungi, particularly plant pathogens. When employed in the treatment of plant fungal diseases, the compounds are applied to the plants in a disease inhibiting and &#34;phytologically acceptable amount&#34;. The term &#34;disease inhibiting&#34; and &#34;phytologically acceptable amount,&#34; as used herein, refers to an amount of a compound of the invention which kills or inhibits the plant disease for which control is desired, but is not significantly toxic to the plant. This amount will generally be from about 1 to 1000 ppm, with 10 to 500 ppm being preferred. The exact concentration of compound required varies with the fungal disease to be controlled, the type formulation employed, the method of application, the particular plant species, climate conditions and the like. The compounds of the invention may also be used to protect stored grain and other non-plant loci from fungal infestation. 
     Greenhouse Tests 
     The following experiments were performed in the laboratory, to determine the fungicidal efficacy of the compounds of the invention. 
     Test 1 
     This screen was used to evaluate the efficacy of the present compounds against a variety of different organisms that cause plant diseases. 
     The test compounds were formulated for application by dissolving 50 mg of the compound into 1.25 ml of solvent. The solvent was prepared by mixing 50 ml of &#34;Tween 20&#34; with 475 ml of acetone and 475 ml of ethanol. The solvent/compound solution was diluted to 125 ml with deionized water. The resulting formulation contains 400 ppm test chemical. Lower concentrations were obtained by serial dilution with the solvent-surfactant mixture. 
     The formulated test compounds were applied by foliar spray. The following plant pathogens and their corresponding plants were employed. 
     
         ______________________________________           Designation inPathogen        Following Tables                        Host______________________________________Erysiphe graminis tritici           POWD         wheat(powdery mildew)           MDEWPyricularia oryzae           RICE         rice(rice blast)    BLASPuccinia recondita tritici           LEAF         wheat(leaf rust)     RUSTBotrytis cinerea           GRAY         grape berries(gray mold)     MOLDPseudoperonospora cubensis           DOWN         squash(downy mildew)  MDEWCercospora beticola           LEAF         sugar beet(leaf spot)     SPOTVenturia inaequalis           APPL         apple seedling(apple scab)    SCABSeptoria tritici           LEAF         wheat(leaf blotch)   BLOT______________________________________ 
    
     The formulated technical compounds were sprayed on all foliar surfaces of the host plants (or cut berry) to past run-off. Single pots of each host plant were placed on raised, revolving pedestals in a fume hood. Test solutions were sprayed on all foliar surfaces. All treatments were allowed to dry and the plants were inoculated with the appropriate pathogens within 2-4 hours. 
     The effectiveness of test compounds in controlling disease was rated on the following scale: 
     
         ______________________________________0 =          not tested against specific organism- =          0-19% control at 400 ppm+ =          20-89% control at 400 ppm++ =         90-100% control at 400 ppm+++ =        90-100% control at 400 ppm.______________________________________ 
    
     Table 13 gives the results. 
     
                                           TABLE 13__________________________________________________________________________EX. POWD RICE LEAF GRAY DOWN LEAF APPL LEAFNO. MDEW BLAST         RUST MOLD MDEW SPOT SCAB BLOT__________________________________________________________________________1   +    +    +    +    ++   0    -    -2   -    -    -    -    +++  0    -    -3   -    ++   +    -    +++  0    -    -4   +    +    ++   -    ++   0    -    -5   ++   ++   +++  -    +++  0    -    +++6   ++   +    +    +    ++   0    -    -7   +    +    +++  -    +++  -    -    +++8   +    ++   +    -    +++  +++  -    +9   +    +    +    -    +++  -    -    -10  ++   +++  +++  -    ++   +++  -    +++11  -    ++   +++  -    ++   +++  -    -12  +    ++   +++  -    ++   +++  -    ++13  -    ++   ++   -    ++   -    -    -14  -    +    +    -    +++  +++  -    -15  -    +    +    -    +++  +++  +    -16  -    +    +    -    +++  +++  -    -17  ++   +    ++   -    ++   0    -    -18  +    ++   ++   +    ++   0    -    -19  +    ++   ++   -    +++  0    -    -20  +    +    +    -    +++  0    -    -21  +    +    +    -    ++   0    -    -22  +    +    +    -    +++  0    -    -23  +    +    +    -    +++  0    -    -24  +    +    +    -    +++  0    -    -25  +    +    ++   -    +++  0    -    -26  +    +    -    -    +++  0    -    -27  +    ++   +    -    +++  0    -    -28  +    ++   +    -    +++  0    -    -29  -    +    +    -    -    0    0    030  -    +    +    -    +++  0    -    -31  ++   +    +    -    +++  0    -    -32  +    +    -    -    +++  0    -    -33  -    +    +    -    +++  0    -    -34  +    +    ++   -    +++  +    -    -35  +    +    +    -    +++  +++  -    -36  +    +++  +++  -    +++  +++  -    +++37  +    -    +    -    +    0    0    038  +    -    ++   -    +++  +    -    -39  +++  +++  +++  -    +++  0    0    040  -    ++   +++  -    +    0    0    041  +    ++   +++  -    ++   +++  -    +42  +++  +    ++   -    +++  +++  -    -43  +    +    -    -    ++   +++  -    -44  +++  +    +    -    +++  +++  +    -45  +    ++   +    -    ++   +++  -    -46  +    ++   +    -    ++   +++  +    +47  +    -    +    -    +    0    0    048  +    +    +    -    ++   +    -    -49  -    +    +    -    +    0    0    050  +++  -    ++   -    +++  -    -    -51  -    +    +    -    +++  +++  -    -52  -    +    +    -    +++  +    -    +++53  +++  +    +    -    +++  +++  -    +54  -    ++   +    -    +++  +++  -    +55  +    ++   +    -    ++   +++  -    -56  -    ++   ++   -    +++  +++  -    +57  -    ++   +    -    ++   +++  -    -58  -    -    +    -    +++  0    0    059  +    +    -    -    -    0    0    060  ++   +++  ++   -    +++  0    0    061  -    ++   ++   -    +++  0    0    062  -    ++   ++   -    +++  -    -    +63  -    +    +++  -    ++   0    0    064  +    -    +    -    +++  0    0    065  +    +    ++   -    +++  -    -    +66  +    ++   +++  -    +++  +++  -    +67  -    +    +    -    ++   +    -    -68  +    +    +++  -    ++   -    -    +++69  +    +    +    -    +++  -    -    -70  + ++ +    +    -    -    -    -    -71  +    +    +++  -    +++  +++  -    +72  ++   +++  +++  -    +++  0    0    073  -    +    -    -    ++   -    -    -74  +    +    +++  -    +++  +++  -    -75  +    +    ++   -    +++  -    -    +76  ++   +++  +++  -    +++  -    +    +++77  +    +    ++   -    +++  -    +    -78  +    ++   +++  -    +++  +++  -    +79  +    ++   ++   -    ++ + +++  -    +80  +    ++   ++   -    +++  +    -    -81  +    ++   ++   -    +++  +    -    -82  +    +++  +++  -    +++  +    -    +++83  +    ++   +++  +++  ++   +    -    -84  +++  ++   ++   -    ++   +    -    -85  -    -    +    -    -    0    0    086  -    -    +    -    +    0    0    087  -    -    +    -    +++  -    -    -88  -    -    ++   -    ++   +    -    -89  -    -    +    -    +++  0    0    090  -    +++  +++  -    +++  0    0    091  +    +    -    -    ++   -    -    -92  +    ++   +++  -    ++   +    -    +++93  -    -    -    -    -    +    -    +94  +    +++  +++  -    +++  +++  -    +95  +    ++   +++  +    +++  +    +    +++96  +    +++  +++  -    +++  +++  -    +++97  +    +++  +++  -    +++  +++  -    +++98  -    +    ++   -    ++   -    -    -99  -    ++   +++  -    +++  +    -    -100 +    +    +    -    +    0    0    0101 +++  -    +    -    +++  +++  +    -102 +    +    -    -    -    0    0    0103 +    ++   ++   -    +++  +    +++  +104 -    -    -    -    ++   +    +    -105 +++  ++   +++  -    +++  +    -    +106 ++   +    +    -    +    +    -    +107 ++   +    +    -    +++  -    -    -108 +    +    ++   -    +    -    -    +++109 +    +    ++   -    +++  0    0    0110 -    +    ++   -    ++   0    0    0111 +    ++   +++  -    +++  -    -    +++112 -    -    +    -    +++  -    -    -113 +    +++  +++  -    +++  -    -    +++114 +++  +++  +++  -    +++  +++  -    +++115 -    +    -    -    +    0    0    0116 -    +    +++  -    +++  +    +    -117 +    +    +    -    +++  +    -    -118 -    +    -    -    -    -    -    -119 +    +    +    -    ++   -    +    +120 -    +    +    -    ++   +++  -    -121 +    -    ++   -    +    0    0    0122 -    ++   +    -    ++   -    -    -123 -    +    +    -    +++  -    -    -124 +++  +    +    -    -    -    -    -125 +    -    -    -    -    0    0    0126 ++   +++  +    -    +    -    -    +127 +    +    +    -    +    0    0    0128 -    +    +    -    -    0    0    0129 -    +    ++   -    +    -    +    -130 -    -    -    -    -    0    0    0131 -    -    -    -    +    0    0    0132 -    -    -    -    -    0    0    0133 -    +    +    -    +    0    0    0134 +    ++   +    -    +++  0    0    0135 -    -    -    -    +++  -    -    +136 +    -    -    -    +++  -    -    -137 +    +++  +    -    +++  0    0    0138 -    +    +    -    +++  0    0    0139 +    +    +    -    ++   -    -    -140 +    +++  +++  -    +++  +++  +    +++141 -    ++   +    -    +    0    0    0142 -    ++   ++   -    +++  0    0    0143 ++   ++   + ++ -    +++  +    -    +144 -    +    ++   -    +++  +    +    -145 -    +    +    -    +++  +    -    -146 -    -    -    -    +    0    0    0147 -    +    +    -    +++  -    -    -148 -    +    +    -    ++   +    -    -149 +    +    ++   -    ++   +++  -    +150 +    +    ++   -    ++   +++  -    +++151 +    +    ++   -    +++  +    -    +152 ++   +++  ++   -    +++  +++  -    +++153 +    ++   ++   -    +    -    -    -154 ++   +    +++  -    +++  +    +    +155 -    +    -    -    +++  -    -    -156 -    +    +    -    +++  -    -    -157 -    ++   ++   -    +++  0    0    0158 +    +++  +++  -    +++  +    -    +++159 ++   +++  +++  -    +++  +    -    +++160 -    +    -    -    -    0    0    0161 +    +    -    -    +    0    0    0162 +    +    ++   -    +++  -    -    -163 ++   +    +++  -    ++   +++  -    -164 -    +    +    +    ++   +    -    -165 +    ++   ++   -    +++  +++  +    -166 +    +    +    -    +++  -    -    +167 +    -    -    -    +    0    0    0168 +    ++   ++   -    +++  -    -    -169 +    ++   +    -    ++   -    -    -170 +    +    ++   -    +    -    -    -171 -    +    +    -    +    +    -    +172 +    +    +    -    +    -    -    -173 +    +    ++   -    +++  +++  -    +174 +    +    ++   -    +++  -    -    +175 +    +    +++  -    +++  -    -    +176 +    +    +    -    ++   +    -    -177 ++   +++  +++  -    +++  0    0    0178 -    +    ++   -    +++  0    0    0179 -    -    -    -    ++   +    +    -180 ++   +    -    -    ++   +    -    +181 +    +    +    -    +++  0    -    -182 -    +    -    -    -    0    0    0183 -    ++   ++   -    +++  +    +    -184 -    +    ++   -    ++   -    -    -185 -    +    +    -    +    0    0    0186 -    -    +    -    +++  +    -    +187 -    +    +    -    +++  -    -    -188 -    ++   +    -    ++   0    0    0189 -    +    +    -    +    -    -    -190 -    +    +++  -    -    -    -    -191 -    +    ++   -    -    0    0    0192 -    -    ++   -    +++  -    -    +193 -    -    +    -    -    0    0    0194 +    -    -    -    -    0    0    0195 +++  +++  +++  -    +++  0    0    0196 +++  +++  +++  -    +++  0    0    0197 +++  +++  +++  -    +    0    0    0198 -    -    -    -    -    0    0    0199 ++   ++   +++  -    +++  0    0    0200 +++  +++  +++  -    +    +    +    +++201 +++  +    +++  -    +++  +++  +    +++202 +++  +    ++   -    ++   +    -    +203 +    +++  +++  -    ++   +    +    ++204 +    -    +    -    +    0    0    0205 ++   +++  +++  -    +++  0    0    0206 +++  +++  +++  -    +++  0    0    0207 ++   +++  +++  -    +++  +    +    +++208 ++   +++  +++  -    +++  +    -    +209 +++  +++  +++  -    +++  +++  +    +++210 ++   +++  +++  -    +++  +    -    +++211 ++   +++  +++  -    +++  +++  -    +++212 ++   +++  +++  -    +++  -    +++  +++213 +    ++   ++   -    +++  -    +    +214 +    +++  +    -    ++   0    0    0215 -    +    +    -    ++   0    0    0216 ++   ++   ++   -    ++   0    0    0217 +++  +++  +++  -    +++  0    0    0218 +++  +++  +++  -    +++  0    0    0219 ++   +++  +++  -    +++  +    +    +220 ++   +    ++   -    ++   -    +    -221 +    -    +++  -    +++  +++  +    +++222 +    +    +++  -    +++  +    +++  +++223 ++   +++  +++  -    -    0    0    0224 ++   +++  +++  -    +++  0    0    0225 ++   +++  +++  -    +++  0    0    0226 +    -    +    -    +    0    0    0227 -    +    +    -    -    0    0    0228 ++   +++  +++  -    +++  +    +++  +++229 +    +++  ++   -    +++  -    -    +230 ++   -    +    -    -    -    -    -231 +    -    -    -    -    0    0    0232 -    -    -    -    -    0    0    0233 +    ++   ++   -    +    -    -    +234 +    +    ++   -    +    +    -    +235 +    ++   ++   -    +    -    -    +236 +++  -    +    -    -    -    -    -237 ++   ++   +    -    -    0    0    0238 +++  +++  +++  +    ++   0    0    0239 +++  ++   ++   -    ++   0    0    0240 -    +    ++   -    -    0    0    0241 -    -    -    -    -    0    0    0242 -    -    -    -    -    0    0    0243 -    -    -    -    -    0    0    0244 +    ++   +    -    +    -    -    +245 +    ++   ++   -    ++   -    -    -246 ++   +++  +++  -    +++  +    +++  +++247 ++   +++  +++  -    +    -    -    +++248 +    -    -    -    -    0    0    0249 -    -    -    -    -    0    0    0250 -    -    +    -    +    0    0    0251 -    +    -    -    +    -    -    -252 ++   ++   +++  -    ++   -    +    +253 +++  ++   +++  -    ++   +    +++  +254 ++   ++   -    -    -    0    0    0255 +    +++  +++  -    +    0    0    0256 +++  +++  +++  -    ++   0    0    0257 +++  +    +++  -    +++  0    0    0258 ++   +++  ++   -    ++   +    -    +259 +    +++  +++  +    +++  -    +++  +++260 ++   +++  +++  -    +++  +    -    +++261 +    +    +++  -    +    -    +    +262 -    ++   +++  -    +++  0    0    0263 +    +    +    -    -    0    0    0264 -    -    +    -    0    0    0    0265 -    ++   ++   -    -    0    0    0266 -    -    -    -    -    0    0    0267 ++   +++  ++   -    +    0    0    0268 +    +++  +++  -    +++  0    0    0269 ++   +++  +++  -    +++  0    0    0270 -    +    -    -    -    0    0    0271 -    +++  +    -    +++  0    0    0272 -    +    -    -    +    0    0    0273 +    ++   +    -    +    0    0    0274 ++   ++   ++   -    +    0    0    0275 +++  +++  +++  -    +++  0    0    0276 +++  -    +    -    -    0    0    0277 ++   -    -    -    -    0    0    0278 +++  +++  +++  -    +++  0    0    0279 -    ++   ++   -    ++   0    0    0280 +++  +++  +++  -    +++  0    0    0281 +    +++  +    -    ++ + 0    0    0282 -    +    -    -    -    0    0    0283 +    +    ++   -    ++   0    0    0284 -    +++  ++   -    +    0    0    0285 -    -    -    -    -    0    0    0286 +    -    +    -    -    0    0    0287 -    -    +    -    ++   0    0    0288 -    +    -    -    +    0    0    0289 +    ++   ++   -    +++  0    0    0290 -    +++  +    -    +++  0    0    0291 +++  +++  +++  -    +++  0    0    0292 -    -    -    -    -    0    0    0293 -    -    ++   -    -    0    0    0294 -    -    -    -    -    0    0    0295 +    +    +    -    ++   0    0    0296 -    ++   ++   -    +    0    0    0297 +++  ++   +++  -    +++  0    0    0298 -    -    -    -    -    0    0    0299 +    ++   +++  -    ++   0    0    0300 +    +++  +++  -    +++  0    0    0301 -    -    +++  -    +++  0    0    0302 +++  +++  +++  -    +++  0    0    0303 +++  +++  +++  -    +++  0    0    0304 +    +++  +++  -    +++  0    0    0305 +    +    -    -    +    0    0    0306 +    +++  +++  -    +++  0    0    0307 -    -    +    -    -    0    0    0308 +    +++  +++  -    +++  0    0    0309 +    +++  +++  -    +++  0    0    0310 -    ++   -    -    -    0    0    0311 +    -    ++   -    ++   0    0    0312 ++   -    +++  -    +++  0    0    0317 ++   +++  +++  -    +++  0    0    0318 -    ++   ++   -    -    0    0    0319 +++  +++  +++  -    ++   0    0    0320 +    +    ++   -    +    0    0    0321 -    +    ++   -    -    0    0    0322 +++  +++  +++  -    +    0    0    0323 +    ++   +++  -    -    0    0    0324 -    -    +    -    +    0    0    0325 ++   ++   +++  -    +++  0    0    0326 -    +    +    -    -    0    0    0327 +++  -    ++   -    +++  0    0    0328 +    -    +++  -    +++  0    0    0__________________________________________________________________________ 
    
     Field Tests 
     Selected compounds were field tested against a variety of plant pathogens. The following table reports pathogens against which compounds of the invention showed activity in these tests. 
     
                       TABLE 14______________________________________COMPOUNDEX. NO.   CROP      PATHOGEN______________________________________ 2        barley    Pyrenophora teres     potato    Phytophthora infestans     tomato    Phytophthora infestans 5        barley    Pyrenophora teres               Rhynchosporium secalis     cucumber  Sphaerotheca fuliginea     grape     Plasmopara viticola     potato    Phytophthora infestans     rape      Alternaria brassica     tomato    Phytophthora infestans 10       barley    Rhynchosporium secalis               Pyrenophora teres               Erysiphe graminis hordei     cucumber  Sphaerotheca fuliginea     wheat     Pseudocercosporella               herpotrichoides               Erysiphe graminis tritici 97       grape     Plasmopara viticola159       barley    Rhynchosporium secalis     grape     Plasmopara viticola     wheat     Puccinia recondita173       grape     Plasmopara viticola200       barley    Rhynchosporium secalis               Pyrenophora teres               Erysiphe graminis hordei     cucumber  Sphaerotheca fuliginea     wheat     Pseudocercosporella               herpotrichoides               Erysiphe graminis tritici212       apple     Podosphaera leucotricha     barley    Pyrenophora teres     grape     Uncinula necator               Plasmopara viticola     rape      Alternaria brassica     rice      Piricularia oryzae212       barley    Rhynchosporium secalis               Pyrenophora teres               Erysiphe graminis hordei     cucumber  Sphaerotheca fuliginea     wheat     Pseudocercosporella               herpotrichoides               Erysiphe graminis tritici219       barley    Rhynchosporium secalis               Pyrenophora teres               Erysiphe graminis hordei     cucumber  Sphaerotheca fuliginea     wheat     Pseudocercosporella               herpotrichoides               Erysiphe graminis tritici221       sugar beet               Erysiphe sp.______________________________________ 
    
     Combinations 
     Fungal disease pathogens are known to develop resistance to fungicides. When strains resistant to a fungicide do develop, it becomes necessary to apply larger and larger amounts of the fungicide to obtain desired results. To retard the development of resistance to new fungicides, it is desirable to apply the new fungicides in combination with other fungicides. Use of a combination product also permits the product&#39;s spectrum of activity to be adjusted. 
     Accordingly, another aspect of the invention is a fungicidal combination comprising at least 1% by weight of a compound of formula (1) in combination with a second fungicide. 
     Contemplated classes of fungicides from which the second fungicide may be selected include: 
     (1) N-substituted azoles, for example propiconazole, triademefon, flusilazol, diniconazole, ethyltrianol, myclobutanil, and prochloraz; 
     (2) pyrimidines, such as fenarimol and nuarimol; 
     (3) morpholines, such as fenpropimorph and tridemorph; 
     (4) piperazines, such as triforine; and 
     (5) pyridines, such as pyrifenox. Fungicides in these five classes all function by inhibiting sterol biosynthesis. Additional classes of contemplated fungicides, which have other mechanisms of action, include: 
     (6) dithiocarbamates, such as maneb and mancozeb; 
     (7) phthalimides, such as captafol; 
     8) isophthalonitrites, such as chlorothalonil; 
     (9) dicarboximides, such as iprodione; 
     (10) benzimidazoles, such as benomyl and carbendazim; 
     (11) 2-aminopyrimidines, such as ethirimol; 
     (12) carboxamides, such as carboxin; and 
     (13) dinitrophenols, such as dinocap. 
     The fungicide combinations of the invention contain at least 1%, ordinarily 20 to 80%, and more typically 50 to 75% by weight of a compound of formula (1). 
     Combination Tests 
     Selected compounds were tested in the greenhouse in combination with other known fungicides against various plant pathogens. Results are reported in Tables 15 and 16. In the tables, the time given under &#34;Time in hours&#34; is the number of hours elapsing between treatment and inoculation. A negative time indicates that the pathogen was inoculated before treatment. In such cases, curative activity was being tested. A positive time indicates that the plants were treated before they were inoculated with pathogen. In such cases, residual or protectant activity was tested. The compounds were formulated and applied as foliar sprays as in Test 1. The results were evaluated on a 1-9 rating scale. These ratings represent the following percent disease control: 
     1=0-19%, 2=20-29%, 3=30-39%, 4=40-59%, 5 
     6=75-89%, 7=90-96%, 8=97-99%, and 9=100%. 
     
                       TABLE 15______________________________________CUCURBIT DOWNY MILDEWCOMPOUND 1 TIME     RATE     RATEPLUS       IN       CMPD 1   CMPD 2COMPOUND 2 HOURS    IN PPM   IN PPM RESULTS______________________________________Ex. 5      4        48.00           8.0               24.00           7.5               12.00           7.0               6.00            1.0nuarimol   4        2.00            1.0               1.00            1.0               0.50            1.0               0.25            1.0nuarimol + Ex. 5      4        2.00     48.00  8.5               1.00     24.00  7.5               0.50     12.00  5.0               0.25      6.00  1.0______________________________________ 
    
     
                       TABLE 16______________________________________CUCURBIT POWDERY MILDEWEx. 5      4        48.00           6.0               24.00           5.0               12.00           1.0               6.00            1.0nuarimol   4        2.00            9.0               1.00            8.0               0.50            7.0               0.25            6.0nuarimol + Ex. 5      4        2.00     48.00  9.0               1.00     24.00  9.0               0.50     12.00  8.0               0.25      6.00  6.0______________________________________ 
    
     Insecticide and Miticide Utility 
     The compounds of the invention are also useful for the control of insects and mites. Therefore, the present invention also is directed to a method for inhibiting an insect or mite which comprises applying to a locus of the insect or mite an insect- or mite-inhibiting amount of a compound of formula (1). 
     The compounds of the invention show activity against a number of insects and mites. More specifically, the compounds show activity against melon aphid, which is a member of the insect order Homoptera. Other members of the Homoptera include leafhoppers, planthoppers, pear pyslla, apple sucker, scale insects, whiteflies, spittle bugs as well as numerous other host specific aphid species. Activity has also been observed against greenhouse thrips, which are members of the order Thysanoptera. The compounds also show activity against Southern armyworm, which is a member of the insect order Lepidoptera. Other typical members of this order are codling moth, cutworm, clothes moth, Indianmeal moth, leaf rollers, corn earworm, European corn borer, cabbage worm, cabbage looper, cotton bollworm, bagworm, eastern tent caterpillar, sod webworm, and fall armyworm. 
     Representative mite species with which it is contemplated that the present invention can be practiced include those listed below. 
     
         __________________________________________________________________________FAMILY      SCIENTIFIC NAME                      COMMON NAME__________________________________________________________________________ACARIDAE       Aleurobius farinae       Rhizoglyphus echinopus                      Bulb mite       Rhizoglyphus elongatus       Rhizoglyphus rhizophagus       Rhizoglyphus sagittatae       Rhizoglyphus tarsalisERIOPHYIDAE       Abacarus farinae                      Grain rust mite       Aceria brachytarsus       Acalitus essigi                      Redberry mite       Aceria ficus       Aceria fraaxinivorus       Aceria granati       Aceria parapopuli       Eriophyes sheldoni                      Citrus bud mite       Aceria tulipae       Aculus carnutus                      Peach silver mite       Aculus schlechtendali                      Apple rust mite       Colomerus vitis                      Grape erineum mite       Eriophyes convolvens       Eriophyes insidiosus       Eriophyes malifoliae       Eriophyes padi       Eriophyes pruni       Epitrimerus pyri                      Pear leaf blister mite       Eriophyes ramosus       Eriophyes sheldoni                      Citrus bud mite       Eriophyes ribis       Phyllocoptes gracilis                      Dryberry mite       Phyllocoptruta oleivora                      Citrus rust mite       Phytoptus ribis       Trisetacus pini       Vasates amygdalina       Vasates eurynotus       Vasates quadripedes                      Maple balddergall mite       Vasates schlechtendaliEUPODIDAE       Penthaleus major                      Winter grain mite       Linopodes spp.NALEPELLIDAE       Phylocoptella avellanae                      Filbert bud mitePENTHALEIDAE       Halotydeus destrustorPYEMOTIDAE       Pyemotes tritici                      Straw itch mite       Siteroptes cerealiumTARSONEMIDAE       Polyphagotarsonemus latus                      Broad mite       Steneotarsonemus pallidus                      Cyclamen miteTENUIPALPIDAE       Brevipalpus californicus       Brevipalpus obovatus                      Privet mite       Brevipalpus lewisi                      Citrus flat mite       Dolichotetranychus floridanus                      Pineapple flase spider                      mite       Tenuipalpes granati       Tenuipalpes pacificusTETRANYCHIDAE       Bryobia arborea       Bryobia practiosa                      Clover mite       Bryobia rubrioculus                      Brown mite       Eotetranychus coryli       Eotetranychus hicoriae                      Pecan deaf scorch mite       Eotetranychus lewisi       Eotetranychus sexmaculatus                      Sixspotted spider mite       Eotetranychus willametti       Eotetranychus banksi                      Texas citrus mite       Oligonychus ilicis                      Southern red mite       Oligonychus pratensis                      Banks grass mite       Oligonychus ununguis                      Spruce spider mite       Panonychus citri                      Citrus red mite       Panonychus ulmi                      European red mite       Paratetranychus modestus       Paratetranychus pratensis       Paratetranychus viridis       Petrobia latens                      Brown wheat mite       Schizotetranychus celarius Bamboo spider mite        Schizotetranychus pratensis       Tetranychus canadensis                      Fourspotted spider mite       Tetranychus cinnabarinus                      Carmine spider mite       Tetranychus mcdanieli                      McDaniel spider mite       Tetranychus pacificus                      Pacific spider mite       Tetranychus schoenei                      Schoene spider mite       Tetranychus urticae                      Twospotted spider mite       Tetranychus turkestani                      Strawberry spider mite       Tetranychus desertorum                      Desert spider mite__________________________________________________________________________ 
    
     The compounds are useful for reducing populations of insects and mites, and are used in a method of inhibiting an insect or mite population which comprises applying to a locus of the insect or arachnid an effective insect- or mite-inactivating amount of a compound of formula (1). The &#34;locus&#34; of insects or mites is a term used herein to refer to the environment in which the insects or mites live or where their eggs are present, including the air surrounding them, the food they eat, or objects which they contact. For example, plant-ingesting insects or mites can be controlled by applying the active compound to plant parts, which the insects or mites eat, particularly the foliage. It is contemplated that the compounds might also be useful to protect textiles, paper, stored grain, or seeds by applying an active compound to such substance. The term &#34;inhibiting an insect or mite&#34; refers to a decrease in the numbers of living insects or mites; or a decrease in the number of viable insect or mite eggs. The extent of reduction accomplished by a compound depends, of course, upon the application rate of the compound, the particular compound used, and the target insect or mite species. At least an insectinactivating or mite-inactivating amount should be used. The terms &#34;insect-inactivating amount&#34; and &#34;miteinactivating amount&#34; are used to describe the amount, which is sufficient to cause a measurable reduction in the treated insect or mite population. Generally an amount in the range from about 1 to about 1000 ppm active compound is used. 
     In a preferred embodiment, the present invention is directed to a method for inhibiting a mite which comprises applying to a plant an effective miteinactivating amount of a compound of formula (1) in accordance with the present invention. 
     MITE/INSECT SCREEN 
     The compounds of Examples 1-295 were tested for miticidal and insecticidal activity in the following mite/ insect screen. 
     Each test compound was formulated by dissolving the compound in acetone/alcohol (50:50) mixture containing 23 g of &#34;TOXIMUL R&#34; (sulfonate/nonionic emulsifier blend) and 13 g of &#34;TOXIMUL S&#34; (sulfonate/nonionic emulsifier blend) per liter. These mixtures were then diluted with water to give the indicated concentrations. 
     Twospotted spider mites (Tetranychus urticae Koch) and melon aphids (Aphis gossypii Glover) were introduced on squash cotyledons and allowed to establish on both leaf surfaces. Other plants in the same treatment pot were left uninfested. The leaves were then sprayed with 5 ml of test solution using a DeVilbiss atomizing sprayer at 10 psi. Both surfaces of the leaves were covered until runoff, and then allowed to dry for one hour. Two uninfested leaves were then excised and placed into a Petri dish containing southern armyworm (Spodopetra eridania Cramer). 
     After standard exposure periods, percent mortality was evaluated. Results are reported in Table 17, where the following abbreviations are used. 
     CRW refers to corn rootworm 
     SAW refers to Southern armyworm 
     SM refers to twospotted spider mites 
     MA refers to melon aphids. 
     
                                           TABLE 17__________________________________________________________________________MITE/INSECT SCREEN   CRW CRW   SAW    SAW   SM    MACOMPOUND   RATE       RESULTS             SM &amp; MA                    RESULTS                          RESULTS                                RESULTSEX. NO. PPM %     RATE PPM                    %     %     %__________________________________________________________________________1       12.00       0     200    0     0     02       12.00       0     200    0     0     03       12.00       0     200    0     0     04       12.00       0     200    0     0     05       12.00       0     200    0     0     06       12.00       0     200    0     0     07       12.00       0     200    0     0     08       12.00       0     200    100   0     09       12.00       0     200    0     0     010      12.00       0     200    0     0     0   24.00       0     400    0     0     011      24.00       60    400    100   0     0   12.00       0     200    80    0     012      24.00       40    400    100   0     0   12.00       0     200    0     0     013      24.00       0     400    0     0     0   12.00       0     200    0     0     014      24.00       0     400    0     0     0   12.00       0     200    0     0     015      24.00       0     400    0     0     0   12.00       0     200    0     0     016      12.00       0     200    0     0     0   24.00       0     400    0     0     017      12.00       0     200    0     0     018      12.00       0     200    0     0     019      12.00       0     200    0     0     020      12.00       0     200    0     0     021      12.00       0     200    0     0     022      12.00       0     200    0     0     023      12.00       0     200    0     0     024      12.00       0     200    0     0     025      12.00       0     200    0     0     026      12.00       0     200    0     0     027      12.00       0     200    0     0     028      12.00       0     200    0     0     029      12.00       0     200    0     0     030      12.00       0     200    0     0     031      12.00       0     200    0     0     032      12.00       0     200    0     0     033      12.00       0     200    0     0     034      12.00       0     200    0     0     035      12.00       0     200    0     0     036      12.00       0     200    0     0     0   24.00       0     400    0     0     0   24.00       0     400    0     0     037      12.00       0     200    0     0     0   24.00       0     400    0     0     038      12.00       0     200    0     0     0   24.00       0     400    0     0     039      24.00       0     400    0     0     0   12.00       0     200    0     0     040      24.00       100   400    80    0     0   12.00       0     200    0     0     041      24.00       0     400    40    0     0   12.00       0     200    80    0     042      24.00       0     400    0     0     0   12.00       0     200    0     0     043      24.00       0     400    0     0     0   12.00       0     200    0     0     044      24.00       0     400    0     0     0   12.00       0     200    0     0     045      12.00       0     200    0     0     0   24.00       0     400    0     0     046      12.00       0     200    0     0     0   24.00       0     400    0     0     047      12.00       0     200    0     0     0   24.00       0     400    0     0     048      12.00       0     200    0     0     0   24.00       0     400    0     0     049      12.00       0     200    0     0     0   24.00       0     400    0     0     050      12.00       0     200    0     0     0   24.00       0     400    0     0     051      12.00       0     200    0     0     0   24.00       0     400    20    0     052      12.00       0     200    0     0     0   24.00       0     400    0     0     053      12.00       0     200    0     0     0   24.00       0     400    0     0     054      12.00       0     200    0     0     055      12.00       0     200    0     0     056      24.00       0     400    80    0     0   12.00       0     200    100   0     057      12.00       0     200    40    0     0   24.00       0     400    50    0     058      24.00       0     400    0     0     059      24.00       0     400    0     0     0   12.00       0     200    0     0     060      24.00       0     400    0     0     0   12.00       0     200    0     0     061      24.00       0     400    0     0     0   12.00       0     200    0     0     062      24.00       0     400    0     0     063      24.00       0     400    0     0     064      24.00       0     400    0     0     0   12.00       0     200    60    0     065      12.00       0     200    0     0     066      12.00       0     200    0     0     067      12.00       0     200    0     0     068      12.00       0     200    0     0     069      12.00       0     200    0     0     070      12.00       0     200    0     0     071      12.00       0     200    0     0     0   12.00       60    200    0     0     072      24.00       0     400    0     0     073      12.00       0     200    0     0     074      12.00       0     200    20    0     0   12.00       0     200    0     0     075      12.00       0     200    0     0     076      12.00       0     200    0     0     0   12.00       0     200    90    0     077      12.00       0     200    0     0     078      12.00       0     200    20    0     0   12.00       0     200    20    0     079      12.00       0     200    10    0     0   12.00       0     200    60    0     080      12.00       0     200    0     0     081      12.00       0     200    0     0     082      12.00       0     200    0     0     083      12.00       0     200    0     0     084      12.00       0     200    10    0     0   24.00       0     400    0     0     085      12.00       0     200    0     0     0   24.00       0     400    0     0     086      12.00       0     200    0     0     0   24.00       0     400    0     0     087      12.00       0     200    0     0     0   24.00       0     400    0     0     088      24.00       0     400    0     0     0   12.00       0     200    0     0     089      24.00       0     400    0     0     0   12.00       0     200    0     0     090      24.00       0     400    0     0     0   12.00       0     200    100   80    8091      12.00       0     200    0     0     092      12.00       0     200    0     0     093      12.00       0     200    0     0     094      12.00       100   200    0     0     095      12.00       0     200    20    0     0   12.00       0     200    40    0     096      12.00       0     200    100   0     0   12.00       0     200    100   0     097      12.00       0     200    0     0     098      12.00       0     200    0     0     099      12.00       0     200    0     0     0100     12.00       0     200    0     0     0   24.00       0     400    0     0     0101     12.00       0     200    0     0     0   24.00       0     400    0     0     0102     12.00       0     200    0     0     0   24.00       0     400    50    0     0103     24.00       0     400    0     0     0   12.00       0     200    0     0     0104     12.00       0     200    0     0     0   24.00       0     400    60    0     0105     12.00       0     200    30    100   80   24.00       0     400    0     0     50106     24.00       0     400    0     0     0107     24.00       0     400    0     0     0   12.00       0     200    0     0     0108     12.00       0     200    0     0     0109     24.00       0     400    0     0     0110     24.00       0     400    0     0     0   12.00       0     200    0     0     0111     12.00       0     200    20    90    0   24.00       0     400    20    80    0112     12.00       0     200    0     0     0   24.00       0     400    0     0     0113     12.00       0     200    100   40    0   24.00       100   400    70    0     0114     24.00       0     400    70    100   30115     24.00       0     400    0     0     0   12.00       0     200    0     0     0116     12.00       0     200    0     0     0117     12.00       0     200    0     0     0   12.00       0     200    0     0     0118     12.00       0     200    0     0     0119     12.00       0     200    0     0     0120     12.00       0     200    0     0     0121     12.00       0     200    0     0     0   24.00       0     400    0     0     0122     24.00       0     400    0     0     0   12.00       0     200    0     0     0123     12.00       0     200    0     0     0124     24.00       0     400    0     0     0   12.00       0     200    0     0     0125     24.00       0     400    0     0     0   12.00       0     200    0     0     0126     12.00       0     200    0     0     0   24.00       0     400    0     0     0127     24.00       0     400    0     0     0   12.00       0     200    0     0     0128     12.00       0     200    0     0     0   24.00       0     400    0     0     0129     12.00       0     200    0     0     0   24.00       0     400    0     0     0130     12.00       0     200    0     0     0   24.00       0     400    0     0     0131     12.00       0     200    0     0     0   24.00       0     400    0     0     0132     12.00       0     200    0     0     0   24.00       0     400    0     0     0133     24.00       0     400    0     0     0   12.00       0     200    0     0     0134     24.00       0     400    0     0     0135     12.00       0     200    0     0     0   24.00       0     400    0     0     0136     12.00       0     200    0     0     0   24.00       0     400    0     0     0137     24.00       0     400    100   80    80138     24.00       0     400    0     0     0139     12.00       0     200    0     0     0140     24.00       0     400    60    0     0   12.00       0     200    0     0     0141     12.00       0     200    0     0     0   24.00       0     400    0     0     0142     12.00       0     200    0     0     0   24.00       0     400    0     0     0143     12.00       0     200    0     0     0   24.00       0     400    0     0     0144     24.00       0     400    0     0     0   12.00       0     200    0     0     0145     24.00       0     400    0     0     0   12.00       0     200    0     0     0146     12.00       0     200    0     0     0   24.00       0     400    0     0     0147     12.00       0     200    0     0     0148     12.00       0     200    0     0     0149     12.00       0     200    0     0     0150     12.00       0     200    0     0     0   12.00       0     200    0     0     0151     12.00       0     200    0     0     0152     12.00       0     200    0     0     0   12.00       0     200    0     0     0153     12.00       0     200    0     0     0154     12.00       0     200    0     0     0   12.00       0     200    0     0     0155     12.00       0     200    0     0     0156     12.00       0     200    0     0     0   12.00       0     200    0     0     0157     24.00       0     400    100   80    0158     12.00       0     200    0     0     0159     12.00       0     200    0     0     0160     24.00       0     400    0     0     0   12.00       0     200    0     0     0161     24.00       40    400    0     0     80   12.00       0     200    0     0     0162     12.00       0     200    0     0     0163     12.00       0     200    0     0     0164     12.00       0     200    0     0     0165     24.00       0     400    0     0     0   12.00       0     200    0     0     0166     12.00       0     200    0     0     0   24.00       0     400    0     0     0167     12.00       0     200    0     0     0   24.00       0     400    0     0     0168     24.00       0     400    0     0     0   12.00       0     200    0     0     0169     24.00       0     400    0     0     0   12.00       0     200    0     0     0170     12.00       0     200    0     0     0171     12.00       0     200    0     0     0172     12.00       0     200    0     0     0173     12.00       0     200    0     0     0174     12.00       0     200    0     0     0175     12.00       0     200    0     0     0176     12.00       0     200    0     0     0177     12.00       0     200    0     0     0   24.00       100   400    0     0     0178     12.00       0     200    0     0     0   24.00       0     400    0     0     0179     12.00       0     200    0     0     0   24.00       0     400    0     0     0180     12.00       0     200    0     0     0   24.00       0     400    0     0     0181     12.00       0     200    0     0     0182     12.00       0     200    0     0     0   24.00       0     400    0     0     0183     12.00       0     200    0     0     0184     12.00       0     200    0     0     0185     24.00       0     400    0     0     0   12.00       0     200    0     0     0186     24.00       0     400    0     0     0   12.00       0     200    0     0     0187     12.00       0     200    0     0     0   24.00       0     400    0     0     0188     24.00       0     400    0     0     0189     12.00       0     200    0     0     0190     12.00       0     200    0     0     0191     12.00       0     200    0     0     0   24.00       0     400    0     0     0192     24.00       0     400    0     0     0   12.00       0     200    0     0     0193     12.00       0     200    0     0     0   24.00       0     400    0     0     0194     24.00       0     400    0     0     0   12.00       0     200    0     0     0195     24.00       0     400    0     0     0196     24.00       0     400    0     100   100197     24.00       0     400    80    90    80198     24.00       0     400    0     90    80199     24.00       100   400    0     0     0200     24.00       0     400    50    100   100   12.00       0     200    0     100   100201     12.00       0     200    0     80    100   24.00       0     400    0     80    100202     12.00       0     200    0     0     0   24.00       0     400    0     0     0203     12.00       0     200    10    0     100   24.00       0     400    0     0     90204     12.00       0     200    0     0     0   24.00       0     400    100   0     50205     24.00       0     400    0     0     0206     24.00       0     400    0     0     0207     12.00       0     200    0     0     0208     12.00       0     200    0     10    10209     12.00       0     200    10    0     0   12.00       0     200    100   0     40210     12.00       0     200    0     0     0211     12.00       0     200    0     10    40212     12.00       0     200    0     0     0213     12.00       0     200    0     0     0214     24.00       0     400    0     0     0215     24.00       0     400    0     100   100216     24.00       100   400    0     0     0217     24.00       0     400    0     0     0218     24.00       0     400    100   0     0219     12.00       0     200    0     0     0220     24.00       0     400    0     0     0   12.00       0     200    0     0     0221     24.00       0     400    0     90    80   12.00       40    200    0     90    90222     24.00       0     400    0     0     40   12.00       0     200    0     0     50223     24.00       0     400    0     0     100   12.00       80    200    0     0     80224     24.00       0     400    0     0     0225     24.00       0     400    0     0     0226     24.00       0     400    0     0     0   12.00       0     200    0     0     0227     12.00       0     200    0     0     0   24.00       0     400    0     0     0228     12.00       0     200    0     0     0   24.00       0     400    0     0     80229     12.00       0     200    0     50    50   24.00       0     400    0     0     0230     12.00       0     200    0     100   90   24.00       0     400    0     80    0231     12.00       0     200    0     90    0   24.00       0     400    0     40    50232     24.00       0     400    30    80    40   12.00       0     200    0     100   70233     12.00       0     200    0     100   50   24.00       0     400    0     80    80234     12.00       0     200    60    50    50   24.00       0     400    0     30    100235     24.00       0     400    0     0     50   12.00       0     200    80    0     0236     24.00       40    400    0     0     30   12.00       0     200    0     0     0   24.00       0     400    0     0     0237     24.00       0     400    0     100   0   12.00       0     200    0     0     0238     24.00       0     400    100   0     0   12.00       0     200    0     100   100239     24.00       0     400    0     0     0   12.00       0     200    0     0     0240     24.00       0     400    0     0     0241     24.00       0     400    0     0     0242     24.00       0     400    0     0     0   12.00       0     200    0     0     0243     24.00       0     400    0     0     0244     12.00       0     200    0     0     40245     12.00       0     200    0     0     0246     12.00       0     200    0     0     0247     24.00       0     400    50    0     0   12.00       0     200    20    90    0248     24.00       0     400    0     0     0249     24.00       0     400    0     0     0250     24.00       0     400    0     0     0251     12.00       0     200    0     0     0252     24.00       0     400    0     90    100   12.00       0     200    0     90    100253     24.00       0     400    0     100   100   12.00       0     200    0     100   90254     24.00       0     400    0     0     0255     24.00       0     400    0     0     0256     24.00       100   400    100   0     0257     24.00       0     400    0     0     0258     24.00       0     400    0     90    100259     24.00       0     400    0     80    80   12.00       0     200    0     100   90260     24.00       40    400    40    0     0   12.00       0     200    100   100   100261     24.00       100   400    80    50    100   12.00       0     200    100   90    100262     12.00       0     200    0     100   100   24.00       0     400    0     100   100263     12.00       0     200    0     0     0   24.00       0     400    0     0     0264     12.00       0     200    0     0     0   24.00       0     400    0     0     0265     12.00       0     200    0     0     0   24.00       0     400    0     0     0266     12.00       0     200    0     0     0   24.00       0     400    0     0     0267     12.00       0     200    0     40    20   24.00       0     400    0     100   100268     12.00       0     200    0     0     0   24.00       0     400    0     80    0269     12.00       0     200    0           30   24.00       40    400    0     0     0270     12.00       0     200    20    0     0   24.00       0     400    0     80    0271     12.00       0     200    0     0     0   24.00       0     400    0     0     0272     12.00       0     200    0     0     0   24.00       0     400    0     20    0273     24.00       0     400    0     0     0274     12.00       0     200    0     100   100   24.00       0     400    0     0     100275     12.00       0     200    0     0     90   24.00       0     400    0     60    100276     12.00       0     200    0     0     0   24.00       0     400    0     60    80277     24.00       0     400    0     0     0278     12.00       0     200    0     60    90   24.00       0     400    100   0     0279     12.00       0     200    0     0     0   24.00       0     400    0     0     80280     12.00       0     200    60    0     0   24.00       0     400    0     0     0281     12.00       0     200    0     0     0   24.00       0     400    0     0     0282     12.00       0     200    0     0     0   24.00       0     400    0     0     0283     12.00       0     200    0     0     80   24.00       0     400    0     80    0284     12.00       0     200    0     0     0   24.00       0     400    0     0     0285     12.00       0     200    0     40    80   24.00       0     400    0     0     0286     12.00       0     200    0     0     0   24.00       0     400    0     0     0287     12.00       0     200    0     0     80   24.00       0     400    0     0     0288     12.00       0     200    0     0     0   24.00       0     400    0     0     0289     12.00       0     200    0     0     0   24.00       0     400    0     0     0290     12.00       0     200    0     80    80   24.00       0     400    0     0     0291     12.00       0     200    0     0     100   24.00       0     400    0     0     0292     12.00       0     200    0     0     30   24.00       0     400    0     0     0293     12.00       0     200    0     0     0   24.00       0     400    0     0     0294     12.00       0     200    0     0     0   24.00       0     400    0     0     0295     12.00       0     200    0     0     0   24.00       0     400    0     0     0296     12.00       0     200    0     0     0   24.00       0     400    0     0     80297     12.00       0     200    100   100   100   24.00       0     400    100   100   100298     12.00       0     200    0     0     0   24.00       0     400    0     0     0299     12.00       0     200    0     0     0   24.00       0     400    0     0     0300     12.00       0     200    20    0     0   24.00       0     400    0     0     0301     12.00       0     200    40    0     0   24.00       0     400    0     0     0302     12.00       0     200    100   100   100   24.00       0     400    0     0     100303     12.00       0     200    0     100   100   24.00       0     400    0     0     100304     12.00       0     200    0     100   100   24.00       0     400    0     100   80305     12.00       0     200    0     0     0   24.00       0     400    0     0     0306     12.00       0     200    0     100   100   24.00       100   400    100   0     0307     12.00       0     200    0     0     0   24.00       0     400    0     0     0308     12.00       0     200    0     0     80   24.00       0     400    0     0     80309     12.00       0     200    0     40    60   24.00       0     400    100   0     0310     12.00       0     200    0     0     0   24.00       0     400    0     0     90311     12.00       0     200    0     0     0   24.00       0     400    0     0     40312     12.00       0     200    0     0     0   24.00       0     400    0     0     0313     12.00     200   24.00       0     400    0     30    0314     24.00       100   400    0     100   100317     12.00       0     200    80    80    80   24.00       0     400    0     0     60318     12.00     200   24.00       0     400    0     0     0319     12.00     200   24.00       0     400    0     100   100320     12.00       0     200    0     0     0   24.00       0     400    0     0     0321     12.00       0     200    0     0     0   24.00       0     400    0     0     0322     12.00       0     200    60    100   80   24.00       0     400    60    80    100323     12.00       0     200    0     0     0   24.00       0     400    0     0     0324     12.00       0     200    0     0     0   24.00       0     400    0     0     0325     12.00       0     200    0     0     80   24.00       0     400    80    0     0326     12.00       0     200    0     0     0   24.00       0     400    0     0     0327     12.00       0     200    80    0     100   24.00       60    400    0     80    60328     12.00       100   200    100   80    80   24.00       100   400    100   0     0__________________________________________________________________________ 
    
     Field Trials 
     4-[2-[4-(t-Butyl)phenyl]ethoxy]-8-fluoroquinoline (Example 221) was evaluated in a number of field trials. The following table reports the host plants on which it was tested and the pest species against which it showed activity. 
     
                       TABLE 18______________________________________HOST            PEST______________________________________alfalfa (Lucerne)           pea aphid, potato leaf hopper,           tarnished plant bug, green           cloverwormapples          mites, apple aphid, European red           mite, green peach aphid, white           apple leafhopper, apple rust mite,           rosy apple aphidazaleas         greenhouse thripbean, faba broad           bean aphidbroccoli        twospotted spider mitecotton          cotton aphidgrape (European)           grape thrip, grape leafhopperhops            Dawson-hop aphidpea, garden (English)           pea aphidpecan nut       yellow hickory aphidprivet          thripsugar beet      green peach aphidwheat           wheat aphid______________________________________ 
    
     Compositions 
     The compounds of this invention are applied in the form of compositions which are important embodiments of the invention, and which comprise a compound of this invention and a phytologically-acceptable inert carrier. The compositions are either concentrated formulations which are dispersed in water for application, or are dust or granular formulations which are applied without further treatment. The compositions are prepared according to procedures and formulae which are conventional in the agricultural chemical art, but which are novel and important because of the presence therein of the compounds of this invention. Some description of the formulation of the compositions will be given, however, to assure that agricultural chemists can readily prepare any desired composition. 
     The dispersions in which the compounds are applied are most often aqueous suspensions or emulsions prepared from concentrated formulations of the compounds. Such water-soluble, water-suspendable or emulsifiable formulations are either solids usually known as wettable powders, or liquids usually known as emulsifiable concentrates or aqueous suspensions. Wettable powders, which may be compacted to form water dispersible granules, comprise an intimate mixture of the active compound, an inert carrier and surfactants. The concentration of the active compound is usually from about 10% to about 90% by weight. The inert carrier is usually chosen from among the attapulgite clays, the montmorillonite clays, the diatomaceous earths, or the purified silicates. Effective surfactants, comprising from about 0.5% to about 10% of the wettable powder, are found among the sulfonated lignins, the condensed naphthalenesulfonates, the naphthalenesulfonates, the alkylbenzenesulfonates, the alkyl sulfates, and nonionic surfactants such as ethylene oxide adducts of alkyl phenols. 
     Emulsifiable concentrates of the compounds comprise a convenient concentration of a compound, such as from about 50 to about 500 grams per liter of liquid, equivalent to about 10% to about 50%, dissolved in an inert carrier which is either a water miscible solvent or a mixture of water-immiscible organic solvent and emulsifiers. Useful organic solvents include aromatics, especially the xylenes, and the petroleum fractions, especially the high-boiling naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha. Other organic solvents may also be used, such as the terpenic solvents including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol. Suitable emulsifiers for emulsifiable concentrates are chosen from conventional nonionic surfactants, such as those mentioned above. 
     Aqueous suspensions comprise suspensions of water-insoluble compounds of this invention, dispersed in an aqueous vehicle at a concentration in the range from about 5% to about 50% by weight. Suspensions are prepared by finely grinding the compound, and vigorously mixing it into a vehicle comprised of water and surfactants chosen from the same types discussed above. Inert ingredients, such as inorganic salts and synthetic or natural gums, may also be added, to increase the density and viscosity of the aqueous vehicle. It is often most effective to grind and mix the compound at the same time by preparing the aqueous mixture, and homogenizing it in an implement such as a sand mill, ball mill, or pistontype homogenizer. 
     The compounds may also be applied as granular compositions, which are particularly useful for applications to the soil. Granular compositions usually contain from about 0.5% to about 10% by weight of the compound, dispersed in an inert carrier which consists entirely or in large part of clay or a similar inexpensive substance. Such compositions are usually prepared by dissolving the compound in a suitable solvent, and applying it to a granular carrier which has been pre-formed to the appropriate particle size, in the range of from about 0.5 to 3 mm. Such compositions may also be formulated by making a dough or paste of the carrier and compound, and crushing and drying to obtain the desired granular particle size. 
     Dusts containing the compounds are prepared simply by intimately mixing the compound in powdered form with a suitable dusty agricultural carrier, such as kaolin clay, ground volcanic rock and the like. Dusts can suitably contain from about 1% to about 10% of the compound. 
     It is equally practical, when desirable for any reason, to apply the compound in the form of a solution in an appropriate organic solvent, usually a bland petroleum oil, such as the spray oils, which are widely used in agricultural chemistry. 
     Insecticides and miticides are generally applied in the form of a dispersion of the active ingredient in a liquid carrier. It is conventional to refer to application rates in terms of the concentration of active ingredient in the carrier. The most widely used carrier is water. 
     The compounds of the invention can also be applied in the form of an aerosol composition. In such compositions the active compound is dissolved or dispersed in an inert carrier, which is a pressure-generating propellant mixture. The aerosol composition is packaged in a container from which the mixture is dispensed through an atomizing valve. Propellant mixtures comprise either low-boiling halocarbons, which may be mixed with organic solvents, or aqueous suspensions pressurized with inert gases or gaseous hydrocarbons. 
     The actual amount of compound to be applied to loci of insects and mites is not critical and can readily be determined by those skilled in the art in view of the examples above. In general, concentrations of from 10 ppm to 5000 ppm of compound are expected to provide good control. With many of the compounds, concentrations of from 100 to 1500 ppm will suffice. For field crops, such as soybeans and cotton, a suitable application rate for the compounds is about 0.5 to 1.5 lb/A, typically applied in 50 gal/A of spray formulation containing 1200 to 3600 ppm of compound. For citrus crops, a suitable application rate is from about 100 to 1500 gal/A spray formulation, which is a rate of 100 to 1000 ppm. 
     The locus to which a compound is applied can be any locus inhabited by an insect or arachnid, for example, vegetable crops, fruit and nut trees, grape vines, and ornamental plants. Inasmuch as many mite species are specific to a particular host, the foregoing list of mite species provides exemplification of the wide range of settings in which the present compounds can be used. 
     Because of the unique ability of mite eggs to resist toxicant action, repeated applications may be desirable to control newly emerged larvae, as is true of other known acaricides. 
     The following formulations of compounds of the invention have been prepared, and are typical of compositions useful in the practice of the present invention. 
     
         ______________________________________A. Aqueous Suspension______________________________________8-Fluoro-N-[2-(2-naphthyl)ethyl]-4-quinolinamine                       12.5%&#34;TERGITOL TMN-6&#34; (nonionic surfactant)                       1.0%&#34;ZEOSYL 200&#34; (silica)       1.0%&#34;AF-100&#34; (silicon based antifoam agent)                       0.2%2% xanthan solution         10.0%&#34;MAKON 10&#34; (10 moles ethyleneoxide nonylphenol                       9.0%surfactant)tap water                   66.3%______________________________________ 
    
     
         ______________________________________B. Emulsifiable Concentrate______________________________________4[-2-[4-( .sub.- t-Butyl)phenyl]ethoxy]-8-fluoroquinoline                      12.4%&#34;EXXON 200&#34; (naphthalene solvent)                      83.6%&#34;TOXIMUL H&#34; (nonionic/anionic surfactant blend)                      2.0%&#34;TOXIMUL D&#34; (nonionic/anionic surfactant blend)                      2.0%______________________________________