Sulfonamide derivatives

Details Sulfonamide derivatives Sulfonamide derivatives

2001-12-18

2003-07-01

Chang, Ceila (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

C558S413000, C568S931000

Reexamination Certificate

active

06586617

ABSTRACT:

This application is a 371 of PCT/JP00/02764 Apr. 17, 2000.
TECHNICAL FIELD
This invention relates to sulfonamide derivatives useful as microbicides for agricultural or horticultural use.
BACKGROUND ART
A lot of microbicides have ever been synthesized and used as microbicides for agriculture or horticulture. They have contributed greatly to supply agricultural products constantly. However, it is well-known that frequent use of restricted number of compounds has led to outbreak of microbes which are resistant to those drugs. In addition, recent rise in demand for the safety and environmental influence of chemical substances has made it desirable to develop safer microbicides for agricultural or horticultural use. This has given an intention to the researches to explore and research novel compounds with microbicidal activity. As for sulfonamide derivatives, a lot of compounds have also been synthesized so far from the interests in their biological or chemical characteristics. A majority of them are, however, synthetic intermediates, medicines, compounds prepared for the aim of elucidating chemical reaction mechanism or reagents. As for sulfonamide derivatives related to microbicides, there may be cited those described in Japanese Patent Publication for Laid-Open 286366/1986, Japanese Patent Publication for Laid-Open 239264/1988, Japanese Patent Publication for Laid-Open 238006/1988, Japanese Patent Publication for Laid-Open 307851/1988, Japanese Patent Publication for Laid-Open 156952/1989, and in J. Med. Chem. 1983, 26, 1741, and in DE19725447, and so on.
Nevertheless, no sulfonamide derivative has been developed yet, which is safe and has little influence on human beings and firm animals, natural enemies, and the environment, and exert excellent protective effects even on drug-resistant microbes.
Disclosure of Invention
The present inventors have made intensive efforts for many years in order to find out compounds which have excellent microbicidal action and solve the problems mentioned above. As the results, they have found that the compounds represented by the formula I
0
or salts thereof.
Formula I
0
:
[wherein, A
0
is (1) an aryl group which may be substituted, or (2) a heterocyclic group which may be substituted, X
0
is (1) a chemical bond, (2) a methylene group which may be substituted or (3) a vinylene group which may be substituted, B
0
is a heterocyclic group which may be substituted or an aryl group which may be substituted, Z
0
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 maybe substituted, (5) —N═CR
1
R
2
(wherein R
1
and R
2
is a hydrogen atom or a hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) —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 —S(O)
n
R
4
(wherein n represents an integer from 0 to 2, and R
4
is a hydrogen atom or a hydrocarbon group which may be substituted)], (hereafter, they may also be mentioned as compounds (I
0
)), or more specifically compounds (I) to (V)(as will be stated below) or salts thereof have unexpectedly a very strong microbicidal activity, while, on the contrary, they revealed only a low toxicity to human being and farm animals, fishes and natural enemies. The present inventors carried out an intensive research based on these findings and have completed the present invention. Thus, the present invention relates to:
[1] A microbicidal composition for agricultural or horticultural use comprising a compound of 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 (except for an isoxazolyl 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 respectively a hydrogen atom or a hydrocarbon 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 described in [1] above, 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 described in [1] above, 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, 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 1 to 5 substituents 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, (xxix) 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,

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