6-acyl-1,2,4-triazine-3,5-dione derivative and herbicides

Abstract

Disclosed are triazine derivative compounds exhibiting sufficient herbicidal activity at low application dosage when they are applied to soils and foliage, and an agrochemical composition using the same, in particular herbicides.

1 - 12 . (canceled) 
     
     
         13 . A triazine derivative or a salt thereof represented by following Formula 2: 
       
         
           
           
               
               
           
         
         wherein B represents a hydroxyl group or a C 1 -C 6  alkoxy group; 
         R 1  represents a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkenyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 3 -C 6  halocycloalkyl group; a C 3 -C 6  halocycloalkyl C 1 -C 6  alkyl group; an amino C 1 -C 6  alkyl group; a nitro C 1 -C 6  alkyl group; a C 1 -C 6  alkylamino C 1 -C 6  alkyl group; a di(C 1 -C 6  alkyl)amino C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylthio C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a hydroxy C 1 -C 6  alkyl group; a phenyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyloxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy C 1 -C 6  alkyl group; a phenyloxy C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylthio C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfinyl C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfonyl C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C 1 -C 6  haloalkoxy C 1 -C 6  alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group; a phenyl C 2 -C 6  alkenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkynyl group which may be substituted with one or more substituents selected from the substituent group α; a C 1 -C 6  alkoxyimino C 1 -C 6  alkyl group; a phenoxyimino C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a di(C 1 -C 6  alkoxy) C 1 -C 6  alkyl group; a (R 31 R 32 N—C═O) C 1 -C 6  alkyl group; a C 1 -C 6  alkoxycarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyloxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylidene aminooxy C 1 -C 6  alkyl group; a formyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkyl group; a C 2 -C 6  alkylidene amino group; a di(C 1 -C 10  alkyl)amino C 1 -C 6  alkylidene amino group; a NR 31 R 32  group; a C 1 -C 6  alkoxy group; a C 2 -C 6  alkenyloxy group; a C 2 -C 6  alkynyloxy group; a C 3 -C 6  cycloalkyloxy group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy group; a C 1 -C 6  haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; a C 1 -C 6  alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C 1 -C 6  alkoxy C 1 -C 6  alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; 
         R 2  represents a hydrogen atom; a C 1 -C 6  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyloxy C 1 -C 6  alkyl group; a di(C 1 -C 6  alkoxy) C 1 -C 6  alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkenyl group which may be substituted with one or more substituents selected from the substituent group α; or a phenyl C 2 -C 6  alkynyl group which may be substituted with one or more substituents selected from the substituent group α; 
         Y and Z represent an oxygen atom or a sulfur atom; 
         R 31  and R 32  each independently represent a C 1 -C 6  alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a benzyl group which may be substituted with one or more substituents selected from the substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyl group; a C 1 -C 10  alkylthio carbonyl group; a C 1 -C 6  alkoxycarbonyl group; a C 1 -C 6  haloalkyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl group; a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α; a benzylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C 1 -C 6  alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, wherein, R 31  and R 32  may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom; 
         wherein, “substituent group α” represents a group selected from a group consisting of a halogen atom; a hydroxyl group; a C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 3 -C 6  halocycloalkyl group; a C 3 -C 6  halocycloalkyl C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy group; a C 3 -C 6  cycloalkyloxy group; a C 2 -C 6  alkenyloxy group; a C 2 -C 6  alkynyloxy group; a C 1 -C 6  alkylcarbonyloxy group; a C 1 -C 6  haloalkoxy group; a C 1 -C 6  alkylthio group; a C 1 -C 6  alkylsulfinyl group; a C 1 -C 6  alkylsulfonyl group; a C 1 -C 6  haloalkylthio group; a C 1 -C 6  haloalkylsulfinyl group; a C 1 -C 6  haloalkylsulfonyl group; an amino group; a C 1 -C 6  alkylcarbonylamino group; a mono(C 1 -C 6  alkyl)amino group; a di(C 1 -C 6  alkyl)amino group; a hydroxy C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylthio C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfonyl C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkoxy group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy group; a C 1 -C 6  haloalkoxy C 1 -C 6  alkoxy group; a cyano C 1 -C 6  alkoxy group; a C 1 -C 6  acyl group; a C 1 -C 6  alkoxyimino C 1 -C 6  alkyl group; a carboxyl group; a C 1 -C 6  alkoxycarbonyl group; a carbamoyl group; a mono(C 1 -C 6  alkyl)aminocarbonyl group; a di(C 1 -C 6  alkyl)aminocarbonyl group; a nitro group; a cyano group; a phenyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; and a C 3 -C 6  alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group; and 
         “substituent group β” represents a group selected from a group consisting of a halogen atom, a nitro group, a cyano group, a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 1 -C 6  alkoxy group, and a C 1 -C 6  haloalkoxy group. 
       
     
     
         14 . The triazine derivative or the salt thereof according to  claim 13 , wherein
 Y in Formula 2 is an oxygen atom,   R 1  in Formula 2 represents a group selected from a group consisting of a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkenyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkoxyimino C 1 -C 6  alkyl group; a C 1 -C 6  alkoxycarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyl C 1 -C 6  alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C 1 -C 6  alkyl group; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; and   R 2  in Formula 2 represents a group selected from a group consisting of a C 1 -C 6  alkyl group; a C 1 -C 6  haloalkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α.   
     
     
         15 . The triazine derivative or the salt thereof according to  claim 14 , wherein
 Y in Formula 2 is an oxygen atom,   R 1  in Formula 2 represents a group selected from a group consisting of a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkenyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkoxyimino C 1 -C 6  alkyl group; a C 1 -C 6  alkoxycarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyl C 1 -C 6  alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group; and a heterocyclic group selected from the group consisting of pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, thienyl group, thiazolyl group, isoxazolyl group, pyrazolyl group, morpholinyl group, thiomorpholinyl group, and piperazinyl group, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone;   R 2  is a group selected from a group consisting of a C 1 -C 6  alkyl group; a C 1 -C 6  haloalkyl group; and a pyridyl group; and,   “substituent group α” represents a group selected from a group consisting of a halogen atom; a C 1 -C 6  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 1 -C 6  haloalkyl group; a C 1 -C 6  alkoxy group; a C 1 -C 6  haloalkoxy group; a C 1 -C 6  alkylthio group; a C 1 -C 6  alkylsulfinyl group; a C 1 -C 6  alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a methylenedioxy group.   
     
     
         16 . The triazine derivative or a salt thereof of  claim 13 , wherein Y and Z are each oxygen, R 1  is 4-F-Ph, R 2  is Me, and B is ethoxy. 
     
     
         17 . The triazine derivative or a salt thereof of  claim 13 , wherein Y and Z are each oxygen, R 1  is 4-F-Ph, R 2  is Me, and B is OH. 
     
     
         18 . A method of preparing a compound of Formula 13b, comprising treating a compound of Formula 13a with a sulfurizing agent, 
       
         
           
           
               
               
           
         
         wherein
 R 1  represents a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkenyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 3 -C 6  halocycloalkyl group; a C 3 -C 6  halocycloalkyl C 1 -C 6  alkyl group; an amino C 1 -C 6  alkyl group; a nitro C 1 -C 6  alkyl group; a C 1 -C 6  alkylamino C 1 -C 6  alkyl group; a di(C 1 -C 6  alkyl)amino C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylthio C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a hydroxy C 1 -C 6  alkyl group; a phenyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyloxy c 1 -c 6  alkyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy C 1 -C 6  alkyl group; a phenyloxy C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylthio C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfinyl C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfonyl C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C 1 -C 6  haloalkoxy C 1 -C 6  alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group; a phenyl C 2 -C 6  alkenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkynyl group which may be substituted with one or more substituents selected from the substituent group α; a C 1 -C 6  alkoxyimino C 1 -C 6  alkyl group; a phenoxyimino C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a di(C 1 -C 6  alkoxy) C 1 -C 6  alkyl group; a (R 31 R 32 N—C═O) C 1 -C 6  alkyl group; a C 1 -C 6  alkoxycarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyloxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylidene aminooxy C 1 -C 6  alkyl group; a formyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkyl group; a C 2 -C 6  alkylidene amino group; a di(C 1 -C 10  alkyl)amino C 1 -C 6  alkylidene amino group; a NR 31 R 32  group; a C 1 -C 6  alkoxy group; a C 2 -C 6  alkenyloxy group; a C 2 -C 6  alkynyloxy group; a C 3 -C 6  cycloalkyloxy group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy group; a C 1 -C 6  haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; a C 1 -C 6  alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C 1 -C 6  alkoxy C 1 -C 6  alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; 
 R 2  represents a hydrogen atom; a C 1 -C 6  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyloxy C 1 -C 6  alkyl group; a di(C 1 -C 6  alkoxy) C 1 -C 6  alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkenyl group which may be substituted with one or more substituents selected from the substituent group α; or a phenyl C 2 -C 6  alkynyl group which may be substituted with one or more substituents selected from the substituent group α; 
 Z represent an oxygen atom or a sulfur atom; 
 R 31  and R 32  each independently represent a C 1 -C 6  alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a benzyl group which may be substituted with one or more substituents selected from the substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyl group; a C 1 -C 10  alkylthio carbonyl group; a C 1 -C 6  alkoxycarbonyl group; a C 1 -C 6  haloalkyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl group; a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α; a benzylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C 1 -C 6  alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, wherein, R 31  and R 32  may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom; 
 wherein, “substituent group α” represents a group selected from a group consisting of a halogen atom; a hydroxyl group; a C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 3 -C 6  halocycloalkyl group; a C 3 -C 6  halocycloalkyl C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy group; a C 3 -C 6  cycloalkyloxy group; a C 2 -C 6  alkenyloxy group; a C 2 -C 6  alkynyloxy group; a C 1 -C 6  alkylcarbonyloxy group; a C 1 -C 6  haloalkoxy group; a C 1 -C 6  alkylthio group; a C 1 -C 6  alkylsulfinyl group; a C 1 -C 6  alkylsulfonyl group; a C 1 -C 6  haloalkylthio group; a C 1 -C 6  haloalkylsulfinyl group; a C 1 -C 6  haloalkylsulfonyl group; an amino group; a C 1 -C 6  alkylcarbonylamino group; a mono(C 1 -C 6  alkyl)amino group; a di(C 1 -C 6  alkyl)amino group; a hydroxy C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylthio C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfonyl C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkoxy group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy group; a C 1 -C 6  haloalkoxy C 1 -C 6  alkoxy group; a cyano C 1 -C 6  alkoxy group; a C 1 -C 6  acyl group; a C 1 -C 6  alkoxyimino C 1 -C 6  alkyl group; a carboxyl group; a C 1 -C 6  alkoxycarbonyl group; a carbamoyl group; a mono(C 1 -C 6  alkyl)aminocarbonyl group; a di(C 1 -C 6  alkyl)aminocarbonyl group; a nitro group; a cyano group; a phenyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; and a C 3 -C 6  alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group; and 
 “substituent group β” represents a group selected from a group consisting of a halogen atom, a nitro group, a cyano group, a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 1 -C 6  alkoxy group, and a C 1 -C 6  haloalkoxy group. 
 
       
     
     
         19 . The method of  claim 18 , wherein
 Z is an oxygen atom,   R 1  represents a group selected from a group consisting of a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkenyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkoxyimino C 1 -C 6  alkyl group; a C 1 -C 6  alkoxycarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyl C 1 -C 6  alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group; and a heterocyclic group selected from the group consisting of pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, thienyl group, thiazolyl group, isoxazolyl group, pyrazolyl group, morpholinyl group, thiomorpholinyl group, and piperazinyl group, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone;   R 2  is a group selected from a group consisting of a C 1 -C 6  alkyl group; a C 1 -C 6  haloalkyl group; and a pyridyl group; and,   “substituent group α” represents a group selected from a group consisting of a halogen atom; a C 1 -C 6  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 1 -C 6  haloalkyl group; a C 1 -C 6  alkoxy group; a C 1 -C 6  haloalkoxy group; a C 1 -C 6  alkylthio group; a C 1 -C 6  alkylsulfinyl group; a C 1 -C 6  alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a methylenedioxy group.   
     
     
         20 . The method of  claim 19 , wherein R 1  is 4-F-Ph, and R 2  is Me. 
     
     
         21 . A method of preparing a compound of Formula 1a, comprising reacting at least one of a compound of Formula 5a and a compound of Formula 5b with a cyano compound in the presence of a base, 
       
         
           
           
               
               
           
         
         wherein R 1  represents a hydrogen atom; a C 1 -C 12  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkenyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 3 -C 6  halocycloalkyl group; a C 3 -C 6  halocycloalkyl C 1 -C 6  alkyl group; an amino C 1 -C 6  alkyl group; a nitro C 1 -C 6  alkyl group; a C 1 -C 6  alkylamino C 1 -C 6  alkyl group; a di(C 1 -C 6  alkyl)amino C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylthio C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a hydroxy C 1 -C 6  alkyl group; a phenyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyloxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy C 1 -C 6  alkyl group; a phenyloxy C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylthio C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfinyl C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfonyl C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C 1 -C 6  haloalkoxy C 1 -C 6  alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkynyl group which may be substituted with one or more substituents selected from the substituent group α; a C 1 -C 6  alkoxyimino C 1 -C 6  alkyl group; a phenoxyimino C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a di(C 1 -C 6  alkoxy)C 1 -C 6  alkyl group; a (R 31 R 32 N—C═O)C 1 -C 6  alkyl group; a C 1 -C 6  alkoxycarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyloxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylidene aminooxy C 1 -C 6  alkyl group; a formyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkyl group; a C 2 -C 6  alkylidene amino group; a di(C 1 -C 10  alkyl)amino C 1 -C 6  alkylidene amino group; a NR 31 R 32  group; a C 1 -C 6  alkoxy group; a C 2 -C 6  alkenyloxy group; a C 2 -C 6  alkynyloxy group; a C 3 -C 6  cycloalkyloxy group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy group; a C 1 -C 6  haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; a C 1 -C 6  alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C 1 -C 6  alkoxy C 1 -C 6  alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
 R 2  represents a hydrogen atom; a C 1 -C 6  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyloxy C 1 -C 6  alkyl group; a di(C 1 -C 6  alkoxy) C 1 -C 6  alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkenyl group which may be substituted with one or more substituents selected from the substituent group α; or a phenyl C 2 -C 6  alkynyl group which may be substituted with one or more substituents selected from the substituent group α, 
 Y and Z represent an oxygen atom or a sulfur atom, 
 
         A 1  represents a group represented by the following formula 
       
       
         
           
           
               
               
           
         
         
           A 2  represents a group represented by the following formula 
         
       
       
         
           
           
               
               
           
         
         
           A 3  represents a group represented by the following formula 
         
       
       
         
           
           
               
               
           
         
         
           n represents 0, 1, or 2, 
           R 5 , R 6 , R 8 , R 9 , R 35  and R 36  each independently represent a hydrogen atom or a C 1 -C 6  alkyl group, wherein, R 5  and R 8  may be joined together to form a C 2 -C 5  alkylene chain or a C 2 -C 5  alkenylene chain, and may form a ring together with adjacent carbon atoms, and R 5  and R 35  may be joined together to form a C 1 -C 5  alkylene chain to form a ring with adjacent carbon atoms, 
           and 
           R 7 , R 33 , and R 34  each independently represent a hydrogen atom, a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 2 -C 6  alkenyl group, a C 2 -C 6  alkynyl group, or a C 1 -C 6  alkoxy group. 
         
       
     
     
         22 . The method of  claim 21 , wherein the cyano compound is selected from the group consisting of potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymer supported with hydrogen cyanide. 
     
     
         23 . The method of  claim 21 , wherein the reaction proceeds in the presence of a phase transfer catalyst. 
     
     
         24 . The method of  claim 21 , wherein Y and Z are each an oxygen atom. 
     
     
         25 . The method of  claim 21 , wherein R 1  is 4-F-Ph, and R 2  is Me. 
     
     
         26 . A method of preparing a compound of Formula 1a, comprising reacting a compound of Formula 3 with a compound of Formula 4c, 
       
         
           
           
               
               
           
         
         wherein R 1  represents a hydrogen atom; a C 1 -C 12  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 3 -C 6  cycloalkenyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 3 -C 6  halocycloalkyl group; a C 3 -C 6  halocycloalkyl C 1 -C 6  alkyl group; an amino C 1 -C 6  alkyl group; a nitro C 1 -C 6  alkyl group; a C 1 -C 6  alkylamino C 1 -C 6  alkyl group; a di(C 1 -C 6  alkyl)amino C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylthio C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfinyl C 1 -C 6  alkyl group; a C 1 -C 6  haloalkylsulfonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a hydroxy C 1 -C 6  alkyl group; a phenyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyloxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy C 1 -C 6  alkyl group; a phenyloxy C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylthio C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfinyl C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfonyl C 1 -C 6  alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C 1 -C 6  haloalkoxy C 1 -C 6  alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkynyl group which may be substituted with one or more substituents selected from the substituent group α; a C 1 -C 6  alkoxyimino C 1 -C 6  alkyl group; a phenoxyimino C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a di(C 1 -C 6  alkoxy)C 1 -C 6  alkyl group; a (R 31 R 32 N—C═O)C 1 -C 6  alkyl group; a C 1 -C 6  alkoxycarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylcarbonyloxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylidene aminooxy C 1 -C 6  alkyl group; a formyl C 1 -C 6  alkyl group; a C 1 -C 6  alkylthio C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfinyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 1 -C 6  alkylsulfonyl C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a cyano C 1 -C 6  alkyl group; a C 2 -C 6  alkylidene amino group; a di(C 1 -C 10  alkyl)amino C 1 -C 6  alkylidene amino group; a NR 31 R 32  group; a C 1 -C 6  alkoxy group; a C 2 -C 6  alkenyloxy group; a C 2 -C 6  alkynyloxy group; a C 3 -C 6  cycloalkyloxy group; a C 3 -C 6  cycloalkyl C 1 -C 6  alkyloxy group; a C 1 -C 6  haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; a C 1 -C 6  alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C 1 -C 6  alkoxy C 1 -C 6  alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
 R 2  represents a hydrogen atom; a C 1 -C 6  alkyl group; a C 2 -C 6  alkenyl group; a C 2 -C 6  alkynyl group; a C 3 -C 6  cycloalkyl group; a C 1 -C 6  haloalkyl group; a C 2 -C 6  haloalkenyl group; a C 2 -C 6  haloalkynyl group; a C 1 -C 6  alkoxy C 1 -C 6  alkyl group; a C 3 -C 6  cycloalkyloxy C 1 -C 6  alkyl group; a di(C 1 -C 6  alkoxy) C 1 -C 6  alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 1 -C 6  alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C 2 -C 6  alkenyl group which may be substituted with one or more substituents selected from the substituent group α; or a phenyl C 2 -C 6  alkynyl group which may be substituted with one or more substituents selected from the substituent group α, 
 Y and Z represent an oxygen atom or a sulfur atom, 
 
         A 1  represents a group represented by the following formula 
       
       
         
           
           
               
               
           
         
         
           A 2  represents a group represented by the following formula 
         
       
       
         
           
           
               
               
           
         
         
           A 3  represents a group represented by the following formula 
         
       
       
         
           
           
               
               
           
         
         
           n represents 0, 1, or 2, 
           R 5 , R 6 , R 8 , R 9 , R 35  and R 36  each independently represent a hydrogen atom or a C 1 -C 6  alkyl group, wherein, R 5  and R 8  may be joined together to form a C 2 -C 5  alkylene chain or a C 2 -C 5  alkenylene chain, and may form a ring together with adjacent carbon atoms, and R 5  and R 35  may be joined together to form a C 1 -C 5  alkylene chain to form a ring with adjacent carbon atoms, 
           and 
           R 7 , R 33 , and R 34  each independently represent a hydrogen atom, a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 2 -C 6  alkenyl group, a C 2 -C 6  alkynyl group, or a C 1 -C 6  alkoxy group. 
         
       
     
     
         27 . The method of  claim 26 , wherein Y and Z are each an oxygen atom. 
     
     
         28 . The method of  claim 26 , wherein the reaction proceeds in the presence of a Lewis acid. 
     
     
         29 . The method of  claim 26 , wherein the reaction proceeds in the presence of a base. 
     
     
         30 . The method of  claim 26 , wherein R 1  is 4-F-Ph, and R 2  is Me.