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(12) United States Patent (10) Patent No.: US 6,586,617 B1 Tabuchi Et Al

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(12) United States Patent (10) Patent No.: US 6,586,617 B1 Tabuchi Et Al USOO65866.17B1 (12) United States Patent (10) Patent No.: US 6,586,617 B1 Tabuchi et al. (45) Date of Patent: Jul. 1, 2003 (54) SULFONAMIDE DERIVATIVES JP 63-307851 12/1988 JP 1-156952 6/1989 (75) Inventors: Takanori Tabuchi, Tsukuba (JP); WO 96/36596 11/1996 WO 97/24135 7/1997 Tetsuhiro Yamamoto, Toride (JP); WO 97/31910 9/1997 Masaharu Nakayama, Tsukuba (JP) WO 98/45.255 10/1998 (73) Assignee: Sumitomo Chemical Takeda Agro WO 99/06037 2/1999 Company, Limited, Tokyo (JP) WO OO/50391 8/2000 OTHER PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 Derek R. Buckle et al., “Inhibition of Cyclic Nucleotide U.S.C. 154(b) by 0 days. Phosphodiesterase by Derivatives of 1,3-Bis(cyclopropyl methyl)xanthine”, J. Med. Chem., vol. 37, No. 4, pp. (21) Appl. No.: 09/958,953 476-485, 1994. (22) PCT Filed: Apr. 17, 2000 Francisca Lopes et al., “Acyloxymethyl as a Drug Protecting Group. Part 6: N-Acyloxymethyl- and N-Aminocarbony (86) PCT No.: PCT/JP00/02764 loxy)methylsulfonamides as Prodrugs of Agents Contain S371 (c)(1), ing a Secondary Sulfonamide Group”, Bioorganic & (2), (4) Date: Dec. 18, 2001 Medicinal Chemistry, vol. 8, No. 4, pp. 707-716, 2000. J.S. Sukla et al., “Studies on Some Newer Possible Biologi (87) PCT Pub. No.: WO00/65913 cally Active Agents: Part II. Synthesis of N-(-aminopropyl)-2-heterocyclic-p-arylidene aminoben PCT Pub. Date: Nov. 9, 2000 ZeneSulphonamides and N(-aminopropyl)-2-heterocyclic (30) Foreign Application Priority Data Sulphanalamides and their Antibacterial Activity, J. Indian Chem. Soc., vol. LVI, pp. 401–403, Apr. 1979. Apr. 28, 1999 (JP) ........................................... 11-123162 D. Buckle et al., “Inhibition of Cyclic Nucleotide Phos (51) Int. Cl." .............................................. C07C 255/50 phodiesterase by Derivatives of 1,3-Bis(cyclopropylmeth (52) U.S. Cl. ........................ 558/394; 558/413; 568/931 yl)xanthine”, J. Med. Chem., vol. 37, No. 4, pp. 476-485, (58) Field of Search ................................. 558/394, 413; 1994. 568/931 F. Lopes et al., “Acyloxymethyl as a Drug Protecting Group. Part 6: N-Acyloxymethyl- and N-(Aminocarbonyloxy)m- (56) References Cited ethylsulfonamides as Prodrugs of Agents Containing a Secondary Sulfonamide Group”, Bioorganic & Medicinal U.S. PATENT DOCUMENTS Chemistry., vol. 8, No. 4, pp. 707-716, 2000. 3,772,320 A 11/1973 Zellerhoff et al. ....... 548/332.5 J. Sukla et al., “Studies on Some Newer Possible Biologi 4,492,683 A 1/1985 Nagpal ....................... 514/542 cally Active Agents: Part II. Synthesis of 4.853,328 A 8/1989 Okazaki et al. ............... 435/28 N-(y-aminopropyl)-2-heterocyclic-p-arylidene aminoben 4,906,650 A 3/1990 Beck et al. ................. 514/369 ZeneSulphonamides and N'(y-amino-propyl)-2-hetero 5,026,625 A 6/1991 Riediker et al. ............ 430/281 cyclic Sulphanalamides and their Antibacterial Activity”, J. 5,612,353 A 3/1997 Ewing et al. ........ ... 514/309 Indian Chem. Soc., vol. LVI, pp. 401-403, Apr. 1979. 6,130,320 A * 10/2000 Lamm et al. ............... 534/642 Warner M. Linfield et al., Antibacterially Substituted Anil FOREIGN PATENT DOCUMENTS ides of Carboxylic and Sulfonic Acids, J. Med. Chem., 26, DE 19725447 A1 12/1997 pp. 1741–1746, 1983. EP O 206581 12/1986 * cited by examiner EP 0206581 A2 12/1986 EP 432892 6/1991 Primary Examiner-Ceila Chang EP O57O 594 11/1993 ASSistant Examiner-Golam M. M. Shameem EP O 621. 273 10/1994 EP O 778 267 6/1997 (74) Attorney, Agent, or Firm Wenderoth, Lind & Ponack, EP 1044. 962 10/2000 LLP. FR 2 OOO 450 9/1969 HU 191 O74 1/1987 (57) ABSTRACT HU 198371 10/1989 JP 61-286366 12/1986 The present invention relates to microbicides for agricultural JP 62-1901.04 8/1987 or horticultural use containing a Sulfonamide derivative. JP 63-227552 9/1988 JP 63-238.006 10/1988 6 Claims, No Drawings US 6,586,617 B1 1 2 SULFONAMIDE DERVATIVES be Substituted, formyl group or an alkylsulfonyl group which may be substituted), or (8) a -S(O), R(wherein n This application is a 371 of PCT/JP00/02764 Apr. 17, represents an integer from 0 to 2, and R' is a hydrogen atom or a hydrocarbon group which may be substituted), 2OOO. (hereafter, they may also be mentioned as compounds (I)), TECHNICAL FIELD or more specifically compounds (I) to (V)(as will be stated below) or salts thereof have unexpectedly a very strong This invention relates to Sulfonamide derivatives useful as microbicidal activity, while, on the contrary, they revealed microbicides for agricultural or horticultural use. only a low toxicity to human being and farm animals, fishes BACKGROUND ART and natural enemies. The present inventors carried out an intensive research based on these findings and have com A lot of microbicides have ever been synthesized and used pleted the present invention. Thus, the present invention as microbicides for agriculture or horticulture. They have relates to: contributed greatly to Supply agricultural products con 1 A microbicidal composition for agricultural or horti stantly. However, it is well-known that frequent use of 15 cultural use comprising a compound of Formula (I): restricted number of compounds has led to outbreak of microbes which are resistant to those drugs. In addition, Al-X-SO-N-Bl recent rise in demand for the Safety and environmental influence of chemical Substances has made it desirable to 71 develop Safer microbicides for agricultural or horticultural use. This has given an intention to the researches to explore or a salt thereof and research novel compounds with microbicidal activity. wherein A' is (1) an aryl group which may be substituted AS for Sulfonamide derivatives, a lot of compounds have or (2) a heterocyclic group which may be Substituted, also been Synthesized So far from the interests in their X" is (1) a chemical bond, (2) a methylene group which biological or chemical characteristics. A majority of them 25 may be Substituted, or (3) a vinylene group which may are, however, Synthetic intermediates, medicines, com be substituted, B' is a five-membered heterocyclic pounds prepared for the aim of elucidating chemical reaction group (except for an isoxazolyl group) or a condensed mechanism or reagents. AS for Sulfonamide derivatives heterocyclic group which may be Substituted, Z' is (1) related to microbicides, there may be cited those described a hydrocarbon group which may be Substituted, (2) an in Japanese Patent Publication for Laid-Open 286366/1986, acyl group which may be Substituted, (3) formyl group, Japanese Patent Publication for Laid-Open 239264/1988, (4) an amino group which may be Substituted, (5) a Japanese Patent Publication for Laid-Open 238006/1988, group which is represented by -N=CR'R' (wherein Japanese Patent Publication for Laid-Open 307851/1988, each R' and R is respectively a hydrogen atom or a Japanese Patent Publication for Laid-Open 156952/1989, hydrocarbon group which may be Substituted), (6) a and in J. Med. Chem. 1983, 26, 1741, and in DE 19725447, 35 cyclic amino group, (7) a group which is represented by and So on. -OR (wherein R is a hydrogen atom, a hydrocarbon Nevertheless, no Sulfonamide derivative has been devel group which may be Substituted, an acyl group which oped yet, which is Safe and has little influence on human may be Substituted, formyl group or an alkylsulfonyl beings and firm animals, natural enemies, and the group which may be Substituted) or (8) a group repre environment, and exert excellent protective effects even on 40 sented by -S(O), R (wherein, n stands for an integer drug-resistant microbes. from 0 to 2, R" stands for a hydrogen atom or a hydrocarbon group which may be Substituted). Disclosure of Invention 2 A microbicidal composition for agricultural or horti The present inventors have made intensive efforts for cultural use described in 1) above, wherein B is a five many years in order to find out compounds which have 45 membered heterocyclic group which contains hetero-atoms excellent microbicidal action and Solve the problems men Selected from nitrogen atoms and Sulfur atoms as the ring tioned above. As the results, they have found that the constructing hetero atom in addition to the carbon atoms compounds represented by the formula I" or salts thereof. which may be substituted, or B is a condensed heterocyclic Formula I: group which may be Substituted. 50 3. A microbicidal composition described in 1 above, wherein A' is (1) an aryl group which may be substituted with 1 to 5 substituents selected from a group of substituents 70 (T) which consists of (i) a C- alkyl group which may be substituted with 1 to 5 substituents selected from halogens, wherein, A is (1) an aryl group which may be Substituted, 55 hydroxy, imino, hydroxy imino, C. alkoxyimino, or (2) a heterocyclic group which may be substituted, X" is hydrazono, mono- or di-C alkylhydrazono and C. (1) a chemical bond, (2) a methylene group which may be alkylthio, (ii) a C cycloalkyl group which may be Substi Substituted or (3) a vinylene group which may be tuted with 1 to 5 halogens, (iii) a C- alkenyl group which substituted, B' is a heterocyclic group which may be sub may be substituted with 1 to 5 substituents selected from stituted or an aryl group which may be Substituted, Z” is (1) 60 halogen, cyano, and nitro, (iv) a Cas cycloalkenyl group a hydrocarbon group which may be Substituted, (2) an acyl which may be Substituted with 1 to 5 halogens, (v) a C group which may be Substituted, (3) formyl group, (4) an alkynyl group which may be substituted with 1 to 5 amino group which
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