Sulfonamide derivatives

A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (II):

• 51
• or salt thereof,
• [wherein, A2 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 C1-4 alkyl group which may be substituted with 1 to 5 substituents selected from halogen, hydroxy, imino, hydroxyimino, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (ii) a C3-6 cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) a C2-4 alkenyl group which may be substituted with substituents selected from halogens, cyano and nitro, (iv) a C3-6 cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) a C2-4 alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) a C1-4 alkoxy group which may be substituted with 1 to 5 substitutents selected from halogens and C1-4 alkoxy, (viii) formyloxy group, (ix) a C1-4 alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) a C1-4 alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) a C1-4 alkylthio group which may be substituted with 1 to 5 halogens, (xiii) a C1-4 alkyl-carbonylthio group which may be substituted with 1 to 5 halogens,(xiv) a C1-4 alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) a C1-4 alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) a C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) a mono- or di-C1-4 alkylsulfamoyl group, (xix) a group represented by
• 52
• (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 C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, hydroxy, C1-4 alkoxy, formyloxy, C1-4 alkyl-carbonyloxy, formyl and C1-4 alkyl-carbonyl, (xxi) a three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) a C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) a C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) a C1-4 alkylthio-carbonyl group, (xxvi) a C1-4 alkoxy-thiocarbonyl group, (xxvii) a C1-4 alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) a mono- or di-C1-4 alkylcarbamoyl group, (xxx) a group represented by
• 53
• (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) a mono- or di-C1-4 alkyl-thiocarbamoyl group, (xxxiii) a group represented by
• 54
• (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.
• X2 is (1) a chemical bond, (2) a methylene group which may be substituted or (3) a vinylene group which may be substituted, B2 is an aryl group which may be substituted, Z2 is (1) an alkyl group which may be substituted with substitutents selected from mono- or di-C1-6 alkylamino, hydroxy, halogens, C-1-6 alkoxy, C1-6 alkoxy-carbonyl, C1-6 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═CR1R2 (wherein R1 and R2 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 —OR3 (wherein R3 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)nR4 (wherein, n is an integer from 0 to 2, and R4 is hydrogen atom or a hydrocarbon group which may be substituted).

A microbicidal composition for agricultural or horticultural use as claimed in claim 10, wherein A3 is (1) C6-14 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, C1-4 alkoxyimino, hydrazono, mono- or di-C1-4 alkylhydrazono and C1-4 alkylthio, (ii) C3-6 cycloalkyl group which may be substituted with 1 to 5 halogens, (iii) C2-4 alkenyl group which may be substituted with 1 to 5 substituents selected from halogen, cyano and nitro, (iv) C3-6 cycloalkenyl group which may be substituted with 1 to 5 halogens, (v) C2-4 alkynyl group which may be substituted with 1 to 5 halogens, (vi) hydroxy group, (vii) C1-4 alkoxy group which may be substituted with 1 to 5 substitutents selected from halogen and C1-4 alkoxy, (viii) formyloxy group, (ix) C1-4 alkyl-carbonyloxy group which may be substituted with 1 to 5 halogens, (x) C1-4 alkoxy-carbonyloxy group which may be substituted with 1 to 5 halogens, (xi) mercapto group, (xii) C1-4 alkylthio group which may be substituted with 1 to 5 halogens, (xiii) C1-4 alkyl-carbonylthio group which may be substituted with 1 to 5 halogens, (xiv) C1-4 alkoxy-carbonylthio group which may be substituted with 1 to 5 halogens, (xv) C1-4 alkylsulfinyl group which may be substituted with 1 to 5 halogens, (xvi) C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens, (xvii) sulfamoyl group, (xviii) mono- or di-C1-4 alkylsulfamoyl group, (xix) group represented by

• 65
• (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 C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, hydroxy, C1-4 alkoxy, formyloxy, C1-4 alkyl-carbonyloxy, formyl and C1-4 alkyl-carbonyl, (xxi) three- to six-membered cyclic amino group, (xxii) formyl group, (xxiii) C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, (xxiv) C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, (xxv) C1-4 alkylthio-carbonyl group, (xxvi) C1-4 alkoxy-thiocarbonyl group, (xxvii) C1-4 alkylthio-thiocarbonyl group, (xxviii) carbamoyl group, (xxix) mono- or di-C1-4 alkylcarbamoyl group, (xxx) group represented by
• 66
• (wherein, ring C is a three- to six-membered heterocyclic group containing nitrogen), (xxxi) thiocarbamoyl group, (xxxii) mono- or di-C1-4 alkyl-thiocarbamoyl group, (xxxiii) a group represented by
• 67
• (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,
• X3 is (1) chemical bond, (2) methylene group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, halogen atoms and cyano, (3) a vinylene group which may be substituted with one or two substituents selected from C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, halogen atoms and cyano,
• B3 is a six-membered heterocyclic group which is substituted with 1 to 5 substituents selected from the group of substituents (T) mentioned above, Z3 is (1) a hydrocarbon group which is selected from (i) a C1-6 alkyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl, (ii) C2-6 alkenyl which may be substituted with 1 to 5 substituents selected from (a) halogens, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl, (iii) C2-6 alkynyl which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl, (iv) C3-6 cycloalkyl groups which may be substituted with 1 to 5 substituents selected from (a) C1-4 alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C1-4 alkylamino, (e) hydroxy, (f) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C1-4 alkylthio, (i) C1-4 alkylsulfinyl, (j) C1-4 alkylsulfonyl, (k) cyano, (1) C1-4 alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C1-4 alkyl-carbamoyl, (v) C3-6 alkadienyl group which may be substituted with 1 to 5 substituents selected from (a) halogen, (b) amino, (c) mono- or di-C1-4 alkylamino, (d) hydroxy, (e) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (f) mercapto, (g) C1-4 alkylthio, (h) C1-4 alkylsulfinyl, (i) C1-4 alkylsulfonyl, (j) cyano, (k) C1-4 alkoxy-carbonyl, (1) carbamoyl and (m) mono- or di-C1-4 alkyl-carbamoyl, and (vi) C6-14 aryl group which may be substituted with 1 to 5 substituents selected from C1-4 alkyl which may be substituted with 1 to 5 halogens, (b) halogen, (c) amino, (d) mono- or di-C1-4 alkylamino, (e) hydroxy, (f) C1-4 alkoxy which may be substituted with 1 to 5 halogens, (g) mercapto, (h) C1-4 alkylthio, (i) C1-4 alkylsulfinyl, (j) C1-4 alkylsulfonyl, (k) cyano, (l) C1-4 alkoxy-carbonyl, (m) carbamoyl and (n) mono- or di-C1-4 alkyl-carbamoyl, (2) an acyl group selected from (i) C1-4 alkyl-carbonyl, (ii) C1-4 alkoxy-carbonyl, (iii) C1-4 alkylthio-carbonyl, (iv) C1-4 alkoxy-thiocarbonyl, (v) C1-4 alkylthio-thiocarbonyl, (vi) mono- or di-C1-4 alkyl-carbamoyl and (vii) mono- or di-C1-4 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) C1-4 alkyl, (b) C1-4 alkyl-carbonyl which may be substituted with 1 to 5 halogens, (c) C1-4 alkoxy-carbonyl, (d) mono- or di-C1-4 alkyl-carbamoyl, (e) mono- or di-C1-4 alkyl-thiocarbamoyl, (5) a group represented by —N═CR1R2 (wherein, R1 and R2 are the same or different, are hydrogen atom or C1-4 alkyl group), (6) three- to six-membered cyclic amino group, (7) a group represented by —OR3 (wherein, R3 is hydrogen atom, a C1-4 alkyl group which may be substituted with 1 to 5 halogens, a C1-4 alkyl-carbonyl group which may be substituted with 1 to 5 halogens, a C1-4 alkoxy-carbonyl group which may be substituted with 1 to 5 halogens, formyl group or a C1-4 alkylsulfonyl group which may be substituted with 1 to 5 halogens), or (8) a group represented by —OS(O)nR4 (wherein n is an integer from 0 to 2, R4 is (a) hydrogen atom, (b) C1-4 alkyl group which may be substituted with 1 to 5 halogens, or (c) C6-14 aryl group which may be substituted with 1 to 5 C1-4 alkyl groups).

A microbicidal composition for agricultural or horticultural use comprising a compound of Formula (IV)

• 68
• or salt thereof, [wherein, A4 is (1) an aryl group which may be substituted, or (2) a heterocyclic group which may be substituted,
• X4 is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted, B4 is a pyridazinyl group or a pyrazinyl group,
• Z4 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═CR1R2 (wherein R1 and R2 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 —OR3 (wherein, R3 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)nR4 (wherein, n is an integer from 0 to 2, R4 is hydrogen atom or a hydrocarbon group which may be substituted)].