Sulfonamide derivatives

Abstract

The present invention relates to microbicides for agricultural or horticultural use containing sulfonamide derivative of, for example, a formula (I): or a salt thereof, [wherein A 1 is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X 1 is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted, B 1 is a five-membered heterocyclic group comprising nitrogen or sulfur atoms as the ring-constructing atoms except for carbon atoms and may be substituted or a condensed heterocyclic group which may be substituted, Z 1 is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by —N═CR 1 R 2 (wherein each of R 1 and R 2 is a hydrogen atom or a hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) a group represented by —OR 3 (wherein R 3 is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or an alkylsulfonyl group which may be substituted) or (8) —S(O) n R 4 (wherein n stands for an integer from 0 to 2, R 4 stands for a hydrogen atom or a hydrocarbon group which may be substituted). The said compounds or the salts thereof are sulfonamide derivatives with microbicidal action, are useful as excellent microbicides for agricultural or horticultural use, because they are safe, and they have little influence on human beings, farm animals, natural enemies, or the environment, and exert excellent control effects even on resistant microbes.

1 . A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (I):  
       
         
           
           
               
               
           
         
       
       or salt thereof 
 [wherein A 1  is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X 1  is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted, B 1  is a five-membered heterocyclic group (except for an isooxazolyl group) or a condensed heterocyclic group which may be substituted, Z 1  is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group which is represented by —N═CR 1 R 2  (wherein each R 1  and R 2  is repectively a hydrogen atom or a hydrocarobon group which may be substituted), (6) a cyclic amino group, (7) a group which is represented by —OR 3  (wherein R 3  is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or an alkylsulfonyl group which may be substituted) or (8) a group represented by —S(O) n R 4  (wherein, n stands for an integer from 0 to 2, R 4  stands for a hydrogen atom or a hydrocarbon group which may be substituted).] 
 
     
     
         2 . A microbicidal composition for agricultural or horticultural use as claimed in  claim 1 , wherein B 1  is a five-membered heterocyclic group which contains hetero-atoms selected from nitrogen atoms and sulfur atoms as the ring-constructing hetero atom in addition to the carbon atoms which may be substituted, or B 1  is a condensed heterocyclic group which may be substituted.  
     
     
         3 . A microbicidal composition as claimed in  claim 1 , wherein A 1  is (1) an aryl group which may be substituted with 1 to 5 substituents selected from a group of substituents (T) which consists of (i) a C 1-4  alkyl group which may be substituted with 1 to 5 substituents selected from halogens, hydroxyl, imino, hydroxyimino, C 1-4  alkoxyimino, hydrazono, mono- or di-C 1-4  alkylhydrazono and C 1-4  alkylthio, (ii) a C 3-6  cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) a C 2-4  alkenyl group which may be substituted with 1 to 5 substitutents selected from halogen, cyano, and nitro, (iv) a C 3-6  cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C 2-4  alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxyl group, (vii) a C 1-4  alkoxy group which may be substituted with 1 to 5 substituents selected from halogen and C 1-4  alkoxy group, (viii) formyloxy group, (ix) a C 1-4  alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) a C 1-4  alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) a C 1-4  alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C 1-4  alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) a C 1-4  alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C 1-4  alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C 1-4  alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) a sulfamoyl group, (xviii) a mono- or di- C 1-4  alkylsulfamoyl group, (xix) a group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a 3- to 6-membered heterocyclic group containing nitrogen), (xx) an amino group which may be substituted with one or two substituents selected from a C 1-4  alkyl, C 2-4  alkenyl, C 2-4  alkynyl, hydroxy, C 1-4  alkoxy, formyloxy, C 1-4  alkyl-carbonyloxy, formyl and C 1-4  alkyl-carbonyl, (xxi) a 3- to 6-membered cyclic amino group, (xxii) formyl group. (xxiii) a C 1-4  alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) a C 1-4  alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) a C 1-4  alkylthio-carbonyl group, (xxvi) a C 1-4  alkoxy-thiocarbonyl group, (xxvii) C 1-4  alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxiv) a mono- or di-C 1-4  alkylcarbamoyl group, (xxx) a group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a 3- to 6-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) a mono- or di-C 1-4  alkyl-thiocarbamoyl group, (xxxiii) a group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a 3- to 6-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitoroso group, (xlii) nitro group, (xliii) azocyano group, (xliv) azoxycyano group and (xlv) sulfo group, or (2) a heterocyclic group which may be substituted with 1 to 5 substituents selected from the group of substituents (T) mentioned above, 
 X 1  is (1) a chemical bond, (2) a methylene group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 1-4  alkoxy, C 1-4  alkylthio, halogen atom and cyano or (3) a vinylene group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 1-4  alkoxy, C 1-4  alkylthio, halogen atom, and cyano, B 1  is (1) a five-membered heterocyclic group which is composed of the ring-constructing heteroatoms besides carbon atoms selected from nitrogen and sulfur atoms, and which may be substituted with 1 to 5 substituents selected from the group of substituents (T) mentioned above, or (2) a condensed heterocyclic group which is constructed either with a five- to six-membered heterocyclic ring and benzene rings or with a five- to six-membered heterocyclic ring and another (the same or different) five- to six-membered heterocyclic rings and may be substituted with substituents selected from the group of substituents (T) mentioned above, Z 1  is (1) a hydrocarbon group which is selected from (i) a C 1-6  alkyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C 1-4  alkylamino, (d) hydroxy, (e) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C 1-4  alkylthio, (h) C 1-4  alkylsulfinyl, (i) C 1-4  alkylsulfonyl, (j) cyano, (k) C 1-4  alkoxy-carbonyl, (l) carbamoyl and (m) a mono- or di-C 1-4  alkyl-carbamoyl groups, (ii) a C 2-6  alkenyl group which may be substituted with 1 to 5 substituents selected from 
 (a) halogen, (b) amino, (c) mono- or di-C 1-4  alkylamino, (d) hydroxy, (e) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C 1-4  alkylthio, (h) C 1-4  alkylsulfinyl, (i) C 1-4  alkylsulfonyl, (j) cyano, (k) C 1-4  alkoxy-carbonyl, (1) carbamoyl, and (m) mono- or di-C 1-4  alkyl-carbamoyl, (iii) a C 2-6  alkynyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono-or di-C 1-4  alkylamino, (d) hydroxy, (e) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C 1-4  alkylthio, (h) C 1-4  alkylsulfinyl, (i) C 1-4  alkylsulfonyl, (j) cyano, (k) C 1-4  alkoxy-carbonyl, (1) carbamoyl, and (m) mono- or di-C 1-4  alkyl-carbamoyl, (iv) a C 3-6  cycloalkyl group which may be substituted with 1 to 5 substituents selected from (a) C 1-4  alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C 1-4  alkylamino, (e) hydroxy, (f) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C 1-4  alkylthio, (i) C 1-4  alkylsulfinyl, (j) C 1-4  alkylsulfonyl, (k) cyano, (1) C 1-4  alkoxy-carbonyl, (m) carbamoyl, and (n) mono- or di-C 1-4  alkyl-carbamoyl, (v) a C 3-6  alkadienyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- and di-C 1-4  alkylamino, (d) hydroxy, (e) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C 1-4  alkylthio, (h) C 1-4  alkylsulfinyl, (i) C 1-4  alkylsulfonyl, (j) cyano, (k) C 1-4  alkoxy-carbonyl, (l) carbamoyl and (m) mono- or di-C 1-4  alkyl-carbamoyl or (vi) C 6-14  aryl group which may be substituted with 1 to 5 substituents selected from (a) C 1-4  alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C 1-4  alkylamino, (e) hydroxy, (f) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C 1-4  alkylthio, (i) C 1-4  alkylsulfinyl, (j) C 1-4  alkylsulfonyl, (k) cyano, (l) C 1-4  alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C 1-4  alkyl-carbamoyl, (2) an acyl group selected from (i) C 1-4  alkyl-carbonyl, (ii) C 1-4  alkoxy-carbonyl, (iii) C 1-4  alkylthio-carbonyl, (iv) C 1-4  alkoxy-thiocarbonyl, (v) C 1-4  alkylthio-thiocarbonyl, (vi) mono- or di-C 1-4  alkyl-carbamoyl and (vii) mono- or di-C 1-4  alkyl-thiocarbamoyl, each of which may be substituted with 1 to 5 halogens, (3) formyl group, (4) an amino group which may be mono- or substituted with one or two substituents selected from (a) C 1-4  alkyl, (b) C 1-4  alkyl-carbonyl which may be substituted with 1 to 5 halogens, (c) C 1-4  alkoxy-carbonyl, (d) mono- or di-C 1-4  alkyl-carbamoyl and (e) mono- or di-C 1-4  alkyl-thiocarbamoyl, (5) a group represented by —N═CR 1 R 2  (wherein R 1  and R 2  are the same or different, and are a hydrogen arom and a C 1-4  alkyl group), (6) a three- to six-membered cyclic amino group, (7) a group represented by —OR 3  (wherein R 3  is a hydrogen atom, a C 1-4  alkyl group which may be substituted with 1 to 5 halogens, a C 1-4  alkyl-carbonyl group which may be substituted with 1 to 5 halogens, a C 1-4  alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, formyl group or a C 1-4  alkylsulfonyl group which may be substituted with 1 to 5 halogens), or (8) a group represented by —S(O) n R 4  (wherein n is an integer from 0 to 2, and R 4  is (a) hydrogen atom, (b) a C 1-4  alkyl group which may be substituted with 1 to 5 halogens or (c) a C 6-14  aryl group which may be substituted with 1 to 5 C 1-4  alkyl groups.  
 
 
     
     
         4 . A microbicidal composition for agricultural or horticultural use as claimed in  claim 1 , where A 1  is a C 6-14  aryl group which may be substituted with 1 to 3 alkyl group, X 1  is a chemical bond, B 1  is a thienyl group, a pyrazolyl group, an isothiazolyl group, an imidazolyl group, a thiazolyl group, a thiadiazolyl group, a dioxaindanyl group or a imidazopyridyl group, each of which may be substituted with 1 to 5 substituents selected from C 1-4  alkyl which may be substituted with 1 to 5 halogens, C 1-4  alkoxy, C 1-4  alkylthio, cyano, halogens and nitro, Z 1  is a C 1-6  alkyl group or a C 1-4  alkoxy group.  
     
     
         5 . A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (II):  
       
         
           
           
               
               
           
         
       
       or salt thereof, 
 [wherein, A 2  is (1) an aryl group which may be substituted with 1 to 5 substituents selected from a group of substitutents (T′) which consists of (i) a C 1-4  alkyl group which may be substituted with 1 to 5 substituents selected from halogen, hydroxy, imino, hydroxyimino, C 1-4  alkoxyimino, hydrazono, mono- or di-C 1-4  alkylhydrazono and C 1-4  alkylthio, (ii) a C 3-6  cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) a C 2-4  alkenyl group which may be substituted with substituents selected from halogens, cyano and nitro, (iv) a C 3 - 6  cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C 2-4  alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) a C 1-4  alkoxy group which may be substituted with 1 to 5 substitutents selected from halogens and C 1-4  alkoxy, (viii) formyloxy group, (ix) a C 1-4  alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) a C 1-4  alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) a C 1-4  alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C 1-4  alkyl-carbonylthio group which may be substituted with 1 to 5 halogens,(xiv) a C 1-4  alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C 1-4  alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C 1-4  alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) a mono- or di-C 1-4  alkylsulfamoyl group, (xix) a group represented by  
                     
 (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) an amino group which may be mono- or disubstituted with one or two substituents selected from C 1-4  alkyl, C 2-4  alkenyl, C 2-4  alkynyl, hydroxy, C 1-4  alkoxy, formyloxy, C 1-4  alkyl-carbonyloxy, formyl and C 1-4  alkyl-carbonyl, (xxi) a three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) a C 1-4  alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) a C 1-4  alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) a C 1-4  alkylthio-carbonyl group, (xxvi) a C 1-4  alkoxy-thiocarbonyl group, (xxvii) a C 1-4  alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) a mono- or di-C 1-4  alkylcarbamoyl group, (xxx) a group represented by  
                     
 (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) a mono- or di-C 1-4  alkyl-thiocarbamoyl group, (xxxiii) a group represented by  
                     
 (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group and (xliv) sulfo group or (2) a heterocyclic group, which may be substituted.  
 X 2  is (1) a chemical bond, (2) a methylene group which may be substituted or (3) a vinylene group which may be substituted, B 2  is an aryl group which may be substituted, Z 2  is (1) an alkyl group which may be substituted with substitutents selected from mono- or di-C 1-6  alkylamino, hydroxy, halogens, C- 1-6  alkoxy, C 1-6  alkoxy-carbonyl, C 1-6  alkylthio and cyano, (2) vinyl group, (3) an allyl group, (4) a propadienyl group, (5) an alkynyl group which may be substituted, (6) a cycloalkyl group which may be substituted, (7) an aryl group which may be substituted, (8) an acyl group which may be substituted, (9) formyl group, (10) an amino group which may be substituted, (11) a group represented by —N═CR 1 R 2  (wherein R 1  and R 2  are the same or different, and are a hydrogen atom and a hydrocarbon group which may be substituted respectively), (12) a cyclic amino group, (13) a group represented by —OR 3  (wherein R 3  is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group, or an alkylsulfonyl group which may be substituted), or (14) a group represented by —S(O) n R 4  (wherein, n is an integer from 0 to 2, and R 4  is hydrogen atom or a hydrocarbon group which may be substituted).  
 
     
     
         6 . A microbicidal composition for agricultural or horticultural use as claimed in  claim 5 , [wherein, A 2  is (1) a C 6-14  aryl group which may be substituted with 1 to 5 substituents selected from a group of substitutents (T′) which consists of (i) a C 1-4  alkyl group which may be substituted with 1 to 5 substituents selected from halogen, hydroxy, imino, hydroxyimino, C 1-4  alkoxyimino, hydrazono, mono- or di-C 1-4  alkylhydrazono and C 1-4  alkylthio, (ii) a C 3-6  cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) C 2-4  alkenyl group which may be substituted with 1 to 5 substituents selected from halogens, cyano and nitro, (iv) a C 3-6  cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C 2-4  alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) a C 1-4  alkoxy group which may be substituted with 1 to 5 substitutents selected from halogen and C 1-4  alkoxy, (viii) formyloxy group, (ix) a C 1-4  alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) a C 1-4  alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) a C 1-4  alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C 1-4  alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) a C 1-4  alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C 1-4  alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C 1-4  alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) a mono- or di-C 1-4  alkylsulfamoyl group, (xix) a group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) an amino group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 2-4  alkenyl, C 2-4  alkynyl, hydroxy, C 1-4  alkoxy, formyloxy, C 1-4  alkyl-carbonyloxy, formyl and C 1-4  alkyl-carbonyl, (xxi) a three to six-membered cyclic amino group, (xxii) formyl group, (xxiii) a C 1-4  alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) a C 1-4  alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) a C 1-4  alkylthio-carbonyl group, (xxvi) a C 1-4  alkoxy-thiocarbonyl group, (xxvii) a C 1-4  alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) a mono- or di-C 1-4  alkylcarbamoyl group, (xxx) a group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group (xxxii) a mono- or di-C 1-4  alkyl-thiocarbamoyl group, (xxxiii) a group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group and (xliv) sulfo group, or (2) heterocyclic group which may be substituted with 1 to 5 substituents selected from a group of substitutents (T) which consists of (i) C 1-4  alkyl group which may be substituted with 1 to 5 substituents selected from halogens, hydroxy, imino, hydroxyimino, C 1-4  alkoxyimino, hydrazono, mono- or di-C 1-4  alkylhydrazono and C 1-4  alkylthio, (ii) a C 3-6  cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) C 2-4  alkenyl group which may be substituted with 1 to 5 substituents selected from halogen, cyano and nitro, (iv) C 3-6  cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C 2-4  alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) C 1-4  alkoxy group which may be substituted with 1 to 5 substitutents selected from halogen and C 1-4  alkoxy, (viii) formyloxy group, (ix) C 1-4  alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) C 1-4  alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) C 1-4  alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C 1-4  alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) a C 1-4  alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C 1-4  alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C 1-4  alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) a mono- or di-C 1-4  alkylsulfamoyl group, (xix) a group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) an amino group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 2-4  alkenyl, C 2-4  alkynyl, hydroxy, C 1-4  alkoxy, formyloxy, C 1-4  alkyl-carbonyloxy, formyl and C 1-4  alkyl-carbonyl, (xxi) three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) C 1-4  alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) C 1-4  alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) C 1-4  alkylthio-carbonyl group, (xxvi) a C 1-4  alkoxy-thiocarbonyl group, (xxvii) C 1-4  alkylthio-thiocarbonyl group, (xxviii) a carbamoyl group, (xxix) mono- or di-C 1-4  alkylcarbamoyl group, (xxx) group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) mono- or di-C 1-4  alkyl-thiocarbamoyl group, (xxxiii) group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group and (xliv) azoxycyano group, and (xlv) sulfo group, X 2  is (1) a chemical bond, (2) a methylene group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 1-4  alkoxy, C 1-4  alkylthio, halogen atoms, and cyano, or (3) vinylene group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 1-4  alkoxy, C 1-4  alkylthio, halogen atom and cyano, B 2  is an aryl group which may be substituted with 1 to 5 substituents selected from the group of substituents (T) described above, Z 2  is (1) C 1-6  alkyl group which may be substituted with 1 to 5 substitutents selected from mono- or di-C 1-4  alkylamino, hydroxy, halogen, C 1-4  alkoxy, C 1-4  alkoxy-carbonyl, C 1-4  alkylthio and cyano, (2) vinyl group, (3) allyl group, (4) propadienyl group, (5) C 2-6  alkynyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C 1-4  alkylamino, (d) hydroxy, (e) a C 1-4  alkoxy substituted with 1 to 5 halogens, (f) mercapto, (g) C 1-4  alkylthio, (h) C 1-4  alkylsulfinyl, (i) C 1-4  alkylsulfonyl, (j) cyano, (k) C 1-4  alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C 1-4  alkyl-carbamoyl, (6) C 3-6  cycloalkyl group which may be substituted with 1 to 5 substituents selected from (a) C 1-4  alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C 1-4  alkylamino, (e) hydroxy, (f) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C 1-4  alkylthio, (i) C 1-4  alkylsulfinyl, (j) C 1-4  alkylsulfonyl, (k) cyano, (l) C 1-4  alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C 1-4  alkyl-carbamoyl, (7) C 6-14  aryl group which may be substituted with 1 to 5 substituents selected from (a) C 1-4  alkyl which may be substituted with 1 to 5 halogens, (b) halogens, (c) amino, (d) mono- or di-C 1-4  alkylamino, (e) hydroxy, (f) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C 1-4  alkylthio, (i) C 1-4  alkylsulfinyl, (j) C 1-4  alkylsulfonyl, (k) cyano, (l) C 1-4  alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C 1-4  alkyl-carbamoyl, (8) acyl group which may be selected from (i) C 1-4  alkyl-carbonyl, (ii) C 1-4  alkoxy-carbonyl, (iii) C 1-4  alkylthio-carbonyl, (iv) C 1-4  alkoxy-thiocarbonyl, (v) C 1-4  alkylthio-thiocarbonyl, (vi) mono- or di-C 1-4  alkyl-carbamoyl and (vii) mono- or di-C 1-4  alkyl-thiocarbamoyl, each of which may be substituted with 1 to 5 halogens, (9) formyl group, (10) amino group which may be substituted with one or two substituents selected from (a) C 1-4  alkyl, (b) C 1-4  alkyl-carbonyl which may be substituted with 1 to 5 halogens, (c) C 1-4  alkoxy-carbonyl, (d) mono- or di-C 1-4  alkyl-carbamoyl and (e) mono- or di-C 1-4  alkyl-thiocarbamoyl, (11) a group represented by —N═CR 1 R 2  (wherein R 1  and R 2  are the same or different, and are hydrogen atom and a C 1-4  alkyl group), (12) three- to six-membered cyclic amino group, (13) a group represented by —OR 3  (wherein R 3  is hydrogen atom, a C 1-4  alkyl group which may be substituted with 1 to 5 halogens, a C 1-4  alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, formyl group, or C 1-4  alkylsulfonyl group which may be substituted with 1 to 5 halogens), or (14) a group represented by —S(O) n R 4  (wherein n is an integer from 0 to 2, and R 4  (a) hydrogen atom, (b) C 1-4  alkyl group which may be substituted with 1 to 5 halogens or (c) C 6-14  aryl group which may be substituted with 1 to 5 C 1-4  alkyl groups).  
     
     
         7 . A microbicidal composition for agricultural or horticultural use as claimed in  claim 5 , wherein A 2  is (1) C 6-14  aryl group, which may be substituted with 1 to 5 substituents selected from (i) C 1-4  alkyl group which may be substituted with 1 to 5 halogens, (ii) C 1-4  alkoxy group which may be substituted with 1 to 5 halogens, (iii) amino group which may be substituted with one or two C 1-4  alkyl-carbonyl grouop, (iv) C 1-4  alkoxy-carbonyl group, (v) halogen atom, (vi) cyano group and (vii) nitro group, or (2) thienyl group, triazolyl group, imidazolyl group, isooxazolyl group, pyrazolyl group, pyridyl group, quinolyl group, a benzothiadiazolyl group, an imidazothiazolyl group or an imidazopyridyl group, which may be substituted with 1 to 5 substituents selected from (i) C 1-4  alkyl group, (ii) C 1-4  alkoxy-carbonyl group, (iii) carbamoyl group, (iv) mono- or di-C 1-4  alkylcarbamoyl group, (v) C 1-4  alkylsulfonyl group, (vi) halogen atom, (vii) carboxyl group and (viii) cyano group, X 2  is (1) a chemical bond, (2) a methylene group which may substituted with one or two C 1-4  alkyl group, or (3) a vinylene group which may be substituted with one or two C 1-4  alkyl, B 2  is a C 6-14  aryl group which may be substituted with 1 to 5 Substituents selected from (1) a C 1-4  alkyl group which may be substituted with 1 to 5 substituents selected from halogen, hydroxy, imino, hydroxyimino, C 1-4  alkoxyimino, hydrazono,mono- or di-C 1-4  alkylhydrazono and C 1-4  alkylthio, (2) C 2-4  alkynyl group, (3) hydroxy group, (4) a C 1-4  alkoxy group which may be substituted with 1 to 5 substitutents selected from halogens and C 1-4  alkoxy, (5) a C 1-4  alkyl-carbonyloxy group, (6) a C 1-4  alkylthio group, (7) a C 1-4  alkylsulfinyl group, (8) a C 1-4  alkylsulfonyl group, (9) mono- or di-C 1-4  alkylsulfamoyl group, (10) amino group, (11) formyl group, (12) C 1-4  alkoxy-carbonyl group, (13) carbamoyl group, (14) mono- or di-C 1-4  alkylcarbamoyl group, (15) thiocarbamoyl group, (16) halogen atom, (17) carboxyl group, (18) thiocyanato group, (19) cyano group, (20) nitroso group and (21) nitro group, Z 2  is (1) a C 1-6  alkyl group which may be substituted with 1 to 5 substituents selected from mono- or di-C 1-4  alkylamino, hydroxy, halogen, C 1-4  alkoxy, C 1-4  alkoxy-carbonyl, C 1-4  alkylthio and cyano, (2) vinyl group, (3) allyl group, (4) propadienyl group, (5) C 2-6  alkynyl group which may be substituted with 1 to 5 halogens, (6) C 3-6  cycloalkyl group, (7) C 6-14  aryl group, (8) C 1-4  alkyl-carbonyl which may be substituted with 1 to 5 halogens, (9) an amino group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 1-4  alkyl-carbonyl and C 1-4  alkoxy-carbonyl, (10) a group represented by —N═CR 1 R 2  (wherein, both R 1  and R 2  are the same or different C 1-4  alkyl groups), (11) a group represented by —OR 3  (wherein R 3  is a C 1-4  alkyl group or a C 1-4  alkyl-carbonyl group), or (12) a group represented by 
 —S(O) n R 4  (wherein n is an integer from 0 to 2, R 4  is (a) a C 1-4  alkyl group which may be substituted with 1 to 5 halogens, or (b) a C 6-14  aryl group which may be substituted with 1 to 5 C 1-4  alkyl groups).  
 
     
     
         8 . A microbicidal composotion for agricultural or horticultural use as claimed in  claim 5 , wherein    
       
         
           
           
               
               
           
         
       
       or salt thereof, 
 [wherein, A 3  is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X 3  is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted,  
 B 3  is a six-membered heterocyclic group which is substituted with substituents selected from the group of substituents (T), which consists of (i) a C 1-4  alkyl group which may be substituted with 1 to 5 substituents selected from halogen, hydroxy, imino, hydroxyimino, C 1-4  alkoxyimino, hydrazono, mono- or di-C 1-4  alkylhydrazono and C 1-4  alkylthio, (ii) C 3-6  cycloalkyl group which may be substituted with 1 to 5 halogen, (iii) a C 2-4  alkenyl group which may be substituted with 1 to 5 substituents selected from halogens, cyano and nitro, (iv) a C 3-6  cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C 2-4  alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) a C 1-4  alkoxy group which may be substituted with 1 to 5 substitutents selected from halogen and C 1-4  alkoxy group, (viii) formyloxy group, (ix) C 1-4  alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) a C 1-4  alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) a C 1-4  alkylthio group which may be substituted with 1 to 5 halogen, (xiii) a C 1-4  alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) a C 1-4  alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C 1-4  alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C 1-4  alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) a mono- or di-C 1-4  alkylsulfamoyl group, (xix) a group  
 represented by  
                     
 (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) an amino group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 2-4  alkenyl, C 2-4  alkynyl, hydroxy, C 1-4  alkoxy, formyloxy, C 1-4  alkyl-carbonyloxy, formyl and C 1-4  alkyl-carbonyl, (xxi) a three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) a C 1-4  alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) a C 1-4  alkoxy-carbonyl group which may be substituted with 1 to 5 halogens,  
 (xxv) a C 1-4  alkylthio-carbonyl group, (xxvi) a C 1-4  alkoxy-thiocarbonyl group,  
 (xxvii) a C 1-4  alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) a  
 mono- or di-C 1-4  alkylcarbamoyl group, (xxx) a group represented by  
                     
 (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) mono- or di-C 1-4  alkyl-thiocarbamoyl group, (xxxiii) a group which is represented by  
                     
 (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group (xliv) azoxycyano group, and (xlv) sulfo group,  
 Z 3  is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by —N═CR 1 R 2  (wherein, R 1  and R 2  are the same or different, and a hydrogen atom or hydrocarbon group which may be substituted), (6) cyclic amino group, (7) a group represented by —OR 3  (wherein, R 3  stands for a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or sulfonyl group which may be substituted), or (8) a group represented by —S(O) n R 4  (wherein, n is an integer from 0 to 2, R 4  is hydrogen atom or a hydrocarbon group which may be substituted)].  
 
     
     
         11 . A microbicidal composition for agricultural or horticultural use as claimed in claim  10 , wherein A 3  is (1) C 6-14  aryl group which may be substituted with 1 to 5 substituents selected from (i) C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogens, hydroxy, imino, hydroxyimino, C 1-4  alkoxyimino, hydrazono, mono- or di-C 1-4  alkylhydrazono and C 1-4  alkylthio, (ii) C 3-6  cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) C 2-4  alkenyl group which may be substituted with 1 to 5 substituents selected from halogen, cyano and nitro, (iv) C 3-6  cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) C 2-4  alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) C 1-4  alkoxy group which may be substituted with 1 to 5 substitutents selected from halogen and C 1-4  alkoxy, (viii) formyloxy group, (ix) C 1-4  alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) C 1-4  alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) C 1-4  alkylthio group which may be substituted with 1 to 5 halogens, (xiii) C 1-4  alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) C 1-4  alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) C 1-4  alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) C 1-4  alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) mono- or di-C 1-4  alkylsulfamoyl group, (xix) group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xx) amino group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 2-4  alkenyl, C 2-4  alkynyl, hydroxy, C 1-4  alkoxy, formyloxy, C 1-4  alkyl-carbonyloxy, formyl and C 1-4  alkyl-carbonyl, (xxi) three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) C 1-4  alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) C 1-4  alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) C 1-4  alkylthio-carbonyl group, (xxvi) C 1-4  alkoxy-thiocarbonyl group, (xxvii) C 1-4  alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) mono- or di-C 1-4  alkylcarbamoyl group, (xxx) group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) mono- or di-C 1-4  alkyl-thiocarbamoyl group, (xxxiii) a group represented by  
       
         
           
           
               
               
           
         
       
       (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxiv) halogen atom, (xxxv) carboxyl group, (xxxvi) thiocyanato group, (xxxvii) isothiocyanato group, (xxxviii) cyano group, (xxxix) isocyano group, (xl) azido group, (xli) nitroso group, (xlii) nitro group, (xliii) azocyano group (xliv) azoxycyano group, and (xlv) sulfo group, or (2) a heterocyclic group which may be substituted with 1 to 5 substituents selected from a group of substituents (T) above, 
 X 3  is (1) chemical bond, (2) methylene group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 1-4  alkoxy, C 1-4  alkylthio, halogen atoms and cyano, (3) a vinylene group which may be substituted with one or two substituents selected from C 1-4  alkyl, C 1-4  alkoxy, C 1-4  alkylthio, halogen atoms and cyano,  
 B 3  is a six-membered heterocyclic group which is substituted with 1 to 5 substituents selected from the group of substituents (T) mentioned above, Z 3  is (1) a hydrocarbon group which is selected from (i) a C 1-6  alkyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C 1-4  alkylamino, (d) hydroxy, (e) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C 1-4  alkylthio, (h) C 1-4  alkylsulfinyl, (i) C 1-4  alkylsulfonyl, (j) cyano, (k) C 1-4  alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C 1-4  alkyl-carbamoyl, (ii) C 2-6  alkenyl which may be substituted with 1 to 5 substituents selected from (a) halogens, (b) amino, (c) mono- or di-C 1-4  alkylamino, (d) hydroxy, (e) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C 1-4  alkylthio, (h) C 1-4  alkylsulfinyl, (i) C 1-4  alkylsulfonyl, (j) cyano, (k) C 1-4  alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C 1-4  alkyl-carbamoyl, (iii) C 2-6  alkynyl which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C 1-4  alkylamino, (d) hydroxy, (e) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C 1-4  alkylthio, (h) C 1-4  alkylsulfinyl, (i) C 1-4  alkylsulfonyl, (j) cyano, (k) C 1-4  alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C 1-4  alkyl-carbamoyl, (iv) C 3-6  cycloalkyl groups which may be substituted with 1 to 5 substituents selected from (a) C 1-4  alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C 1-4  alkylamino, (e) hydroxy, (f) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C 1-4  alkylthio, (i) C 1-4  alkylsulfinyl, (j) C 1-4  alkylsulfonyl, (k) cyano, (1) C 1-4  alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C 1-4  alkyl-carbamoyl, (v) C 3-6  alkadienyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C 1-4  alkylamino, (d) hydroxy, (e) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C 1-4  alkylthio, (h) C 1-4  alkylsulfinyl, (i) C 1-4  alkylsulfonyl, (j) cyano, (k) C 1-4  alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C 1-4  alkyl-carbamoyl, and (vi) C 6-14  aryl group which may be substituted with 1 to 5 substituents selected from C 1-4  alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C 1-4  alkylamino, (e) hydroxy, (f) C 1-4  alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C 1-4  alkylthio, (i) C 1-4  alkylsulfinyl, (j) C 1-4  alkylsulfonyl, (k) cyano, (l) C 1-4  alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C 1-4  alkyl-carbamoyl, (2) an acyl group selected from (i) C 1-4  alkyl-carbonyl, (ii) C 1-4  alkoxy-carbonyl, (iii) C 1-4  alkylthio-carbonyl, (iv) C 1-4  alkoxy-thiocarbonyl, (v) C 1-4  alkylthio-thiocarbonyl, (vi) mono- or di-C 1-4  alkyl-carbamoyl and (vii) mono- or di-C 1-4  alkyl-thiocarbamoyl, each of these groups may be substituted with 1 to 5 halogens, (3) formyl group, (4) an amino group which may be substituted with one or two substituents selected from (a) C 1-4  alkyl, (b) C 1-4  alkyl-carbonyl which may be substituted with 1 to 5 halogens, (c) C 1-4  alkoxy-carbonyl, (d) mono- or di-C 1-4  alkyl-carbamoyl, (e) mono- or di-C 1-4  alkyl-thiocarbamoyl, (5) a group represented by —N═CR 1 R 2  (wherein, R 1  and R 2  are the same or different, are hydrogen atom or C 1-4  alkyl group), (6) three- to six-membered cyclic amino group, (7) a group represented by —OR 3  (wherein, R 3  is hydrogen atom, a C 1-4  alkyl group which may be substituted with 1 to 5 halogens, a C 1-4  alkyl-carbonyl group which may be substituted with 1 to 5 halogens, a C 1-4  alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, formyl group or a C 1-4  alkylsulfonyl group which may be substituted with 1 to 5 halogens), or (8) a group represented by —OS(O) n R 4  (wherein n is an integer from 0 to 2, R 4  is (a) hydrogen atom, (b) C 1-4  alkyl group which may be substituted with 1 to 5 halogens, or (c) C 6-14  aryl group which may be substituted with 1 to 5 C 1-4  alkyl groups).  
 
     
     
         12 . A microbicidal composition for agricultural or horticultural use as claimed in claim  10 , wherein A 3  is phenyl group which may be substituted with 1 to 5 C 1-4  alkyl groups, or a imidazolyl group which may be substituted with one or two C 1-4  alkyl groups, X 3  is a chemical bond, B 3  is a pyridyl group, a pyridazinyl group or a pyrimidinyl group which is substituted with 1 to 5 substituents selected from C 1-4  alkyl which may be substituted with 1 to 5 halogens, C 1-4  alkoxy, halogen, nitro and cyano, Z 3  is a C 1-6  alkyl group, a C 3-6  cycloalkyl group or a C 1-4  alkoxy group.  
     
     
         13 . A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (IV)  
       
         
           
           
               
               
           
         
       
       or salt thereof, [wherein, A 4  is (1) an aryl group which may be substituted, or (2) a heterocyclic group which may be substituted, 
 X 4  is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted, B 4  is a pyridazinyl group or a pyrazinyl group,  
 Z 4  is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by —N═CR 1 R 2  (wherein R 1  and R 2  are the same or different, and hydrogen atom or hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) a group represented by —OR 3  (wherein, R 3  is hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or a sulfonyl group which may be substituted), or (8) a group represented by —S(O) n R 4  (wherein, n is an integer from 0 to 2, R 4  is hydrogen atom or a hydrocarbon group which may be substituted)].  
 
     
     
         14 . A microbicide for agricultural or horticultural use comprising a compound of Formula (V)  
       
         
           
           
               
               
           
         
       
       or salt thereof, 
 [wherein A 5  is the 4-methylphenyl group, X 5  is a chemical bond, B 5  is a pyridyl or pyrimidinyl group, and Z 5  is a C 1-4  alkyl group].  
 
     
     
         15 . A compound of Formula (VI):  
       
         
           
           
               
               
           
         
       
       or salt thereof, 
 [wherein A 6  is a phenyl group which may be substituted with a substituent or substituents selected from C 1-4  alkyl, halogens and cyano, x 6  is a chemical bond, B 6  is a 2-nitrophenyl group or 2-cyanophenyl group which may be substituted with a substituent or substituents selected from halogens, nitro and cyano, Z 6  is ethyl, isopropyl, cyclopropyl, methoxy, ethoxy or isopropoxy group].  
 
     
     
         16 . A compound or a salt thereof as claimed in  claim 15 , wherein A 6  is a phenyl group which may be substituted with a substituent or substituents selected from C 1-4  alkyl, halogens and cyano, X 6  is a chemical bond, B 6  is a 2-nitrophenyl group which is substituted with a substituent or substituents selected from halogens, nitro and cyano, Z 6  is ethyl, isopropyl, or cyclopropyl group).  
     
     
         17 . A compound or a salt thereof as claimed in  claim 15 , the compound is 4′-chloro-N-ethyl-2′-nitro-p-toluenesulfonanilide, 2′,4′-dinitro-N-ethyl-p-toluenesulfonanilide, 2′,4′-dicyano-N-ethyl-p-toluenesulfonanilide, 4′-chloro-N-isopropyl-2′-nitro-p-toluenesulfonanilide, 4′-fluoro-N-isopropyl-2′-nitro-p-toluenesulfonanilide, 4′-cyano-N-isopropyl-2′-nitro-p-toluenesulfonanilide, 4′-chloro-N-isopropyl-2′-cyano-p-toluenesulfonanilide, 2′,4′-dinitro-N-isopropyl-p-toluenesulfonanilide, 4′-nitro-N-isopropyl-2′-cyano-p-toluenesulfonanilide, 2′-cyano-N-methoxy-4′-nitro-p-toluenesulfonanilide or 2′,4′-dinitro-N-methoxy-p-toluenesulfonanilide or a salt thereof.  
     
     
         18 . A method for manufacturing a compound represented by a Formula:  
       
         
           
           
               
               
           
         
       
       or a salt thereof (wherein each symbol has the same meaning as defined in  claim 15  characterized by: 
 (1) reacting a compound represented by a Formula:  
                     
 or a salt thereof  
 (wherein each symbol has the same meaning as defined in  claim 15  with an electrophile represented by Formula Z 6 -L″ (wherein L″ is a leaving group, and Z 6  has the same meaning as defined in  claim 15 ,  
 (2) reacting a compound represented by a Formula:  
 A 6 -X 6 —SO 2 -L  
 or a salt thereof,  
 (wherein L is a leaving group, and each of other symbols has the same meanings as those defined in  claim 15 , respectively) with an amine or a salt thereof represented by Formula Z 6 HN—B 6  (wherein each symbol has the same meaning as defined in  claim 15 , or, by  
 (3) reacting a compound represented by a Formula:  
 A 6 -X 6 —SO 2 —NHZ 6    
 or a salt thereof  
 (wherein, each symbol has the same meaning as described in  claim 15  to react with a compound or a salt thereof represented by Formula L′-B 6  (wherein L′ is a leaving group, and the other symbol has the same meaning as defined in  claim 15 , respectively), or  
 (4) nitrating a compound represented by a Formula:  
                     
 or a salt thereof  
 (wherein, B 7  is a phenyl group which is substituted with a substituent or substituents selected from halogen, nitro and cyano, provided that both 2- and 6-positions are not substituted at the same time).