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Ep 0128006 B1 Europaisches Paten tamt J European Patent Office C11) Publication number: 0 128 006 B1 Office europeen des brevets EUROPEAN PATENT SPECIFICATION © Date of publication of patent specification: 18.09.91 © Int. Cl.5: C07C 211/39, C07C 229/38, C07C 249/02, C07C 255/24, © Application number: 84303640.1 C07C 257/00, C07C 233/00, C07D 227/00, C07D 307/68, ©@r\n* Date of,«■ f,,,ng:filing: 30.05.84onnco, ^ ^ £ ^ ^^ C07D 251/40 A soil-disease-controlling agent. ® Priority: 31.05.83 JP 97545/83 03.06.83 JP 99959/83 (73) Proprietor: SUMITOMO CHEMICAL COMPANY, 17.08.83 JP 150853/83 LIMITED 18.08.83 JP 151117/83 Kitahama 4-chome 5-33 13.06.83 JP 106233/83 Chuo-ku Osaka 541 (JP) 09.06.83 JP 103949/83 @ Inventor: Tomioka, Hiroki © Date of publication of application: 2-14-7, Mefu 12.12.84 Bulletin 84/50 Takarazuka Hyogo-ken(JP) Inventor: Ooishi, Tadashi © Publication of the grant of the patent: 2-10-2-231, Sonehigashimachi 18.09.91 Bulletin 91/38 Toyonaka Osaka-fu(JP) Inventor: Takahashi, Junya ® Designated Contracting States: 4-2-303, Ryodocho CH DE FR GB IT LI NL Nishinomiya Hyogo-ken(JP) Inventor: Sasaki, Mitsuru References cited: 2-10-1-112, Sonehigashimachi CO DE-A- 1 956 285 GB-A- 806 798 Toyonaka Osaka-fu(JP) CO GB-A- 2 061 913 US-A- 2 512 293 Inventor: Hirata, Naonori o US-A- 3 385 846 US-A- 3 494 105 704-2, 7-510 Kanaokacho o US-A- 3 574 746 US-A- 3 679 699 Sakai Osaka-fu(JP) 00 US-A- 4 204 997 Note: Within nine months from the publication of the mention of the grant of the European patent, any person notice the Patent Office of the CL may give to European opposition to European patent granted. Notice of opposition LU shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid (Art. 99(1) European patent convention). Rank Xerox (UK) Business Services EP 0 128 006 B1 JOURNAL OF ORGANIC CHEMISTRY, vol. 35, no.6, 1970, pages 1861-1866; Washington, US. Representative: Pennant, Pyers et al KUO et al.: "Titanium chloride catalyzed ad- Stevens, Hewlett & Perkins 1 Serjeants' Inn dition of aziridine to ketones. A route to Fleet Street N-aziridinylenamines." London EC4Y1LL(GB) JOURNAL OF THE CHEMICAL SOCIETY PER- KIN J:, 1980, pages 1960-1964; London, GB. M.G. BARLOW et al.: "Polyfluoroalkyl deriva- tives of nitrogen. Part. 49.ENE reactions of trifluoronitrosomethane: Formation of N- trif luoromethylhydroxylamines. " CHEMICAL ABSTRACTS, vol. 88, nr.23, June 5, 1978, page 570, ref.nr.169910z;Columbus, Ohio, US . K.KUBO et al.: "Studies on N- cyclohexylanthranilic acid analogos. I.Synthesis and analgesic activity. "& Yamanouchi Seiyaku Kenkyu Hokoku, 1974 (pub. 1977),3, 8-12. CHEMICAL ABSTRACTS, vo.. 86, nr. 13, March 28, 1977, page 54o, ref. nr. 89766a; Columbus, Ohio, US U.M. Dzhemnilev et al.: "Reaction of secondary amines with cyclic 1,3-dienes catalyzed by nickel complexes." CHEMICAL ABSTRACTS; VOL. 81, NR. 17, OC- TOBER 28, 1974, PAGE 522, REF. NR.1 05396 J;COLUMBUS, OHIO, US. G.S. CHEKRII ET AL: "CYCLIZATION OF 2-R-AMINO DERIVATIVES OF 2-THIAZOLINE." HELVETICA CHIMICA ACTA, vol. 62, Fasc. 7,nr.219, 1979, pages 2129-2153; Basel, CH. M.MARKY et al.: "Photoreaktionen von 1-Alkylbenztriazolen." JOURNAL OF ORGANIC CHEMISTRY; vol. 45, 1980, pages 2709-2710; Washington, US. R. ODLE et al.: "Conversion of 2 halo- N-allylamines to indoles via palladium ( = ) oxidative addition-insertion reactions." CHEMICAL ABSTRACTS, vol. 63, nr. 7, Sep- tember 27, 1965, column 8765a; Columbus, Ohio, US. R.M.GIPSON et al.: "Relation of structure to biological activity of some un- saturated derivatives of cyclopen- taneglycine." EP 0 128 006 B1 TETRAHEDRON, vol. 37, nr. 23, 1981, pages 4007-4016; Oxford, GB, G.E. KECK et al.: "A versatile method for carbon-nitrogen bond formation via ene reactions of acylnitroso compounds." TETRAHEDRON LETTERS, vol. 23, nr. 5o, 1982, pages 5315-5318, Oxford, GB.MIWAKO MORI et al.: "Cyclization of alpha-haloamide with internal double bond by use of the low-valent metal complex." CHEMICAL ABSTRACTS, vol. 91, nr. 23, De- cember 3, 1979, page 624, ref. nr. 193o91r; Columbus, Ohio, US. E. SCHMITZ et al.: "Synthesis of heterocyclic compounds by carbon-carbon bond closure.lll. Syntheses of heterocyclic compounds by in- tramolecular ene reaction." TETRAHEDRON LETTERS, nr. 41, 1966, pages 5061-5065, Pergamon Press Ltd, Oxford, GB H.ZIMMER et al.: "Die Photolyse von Triphenylphosphin-t-Butylimin" JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 17, June 1980, pages 753-758; R.B.MOFFETT.: "Analogs of heterocyclic CNS agents." HELVETICA CHIMICA ACTA, vol. 56, Fasc. nr. 183, 1973, pages 1807-1812; Basel, CH. W.OPPOLZER et al.: "A new stereoselective approach to substituted pyrrolidines by in- tramolecular enereactions." JOURNAL OF ORGANIC CHEMISTRY, vol. 33, nr. 5, May 1968, pages 1844-1846, Washing- ton, US A.M.WEIDLER-KUBANEK et al.: "Addition of hexafluoroacetone to ketenimines." CHEMICAL ABSTRACTS, vol. 84, nr. 21, May 24, 1976, page 535, ref. nr. 150500m; Colum- bus, Ohio, US DD-A-113 903 (E. SCHMITZ et al.) 05-07-1975 JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 5, June 1968, pages 419-421; P.E.FANTA et al.: "Aziridines. XVII. Reactions of 6-azabicyclo (3.1.0) hexane (1)." EP 0 128 006 B1 JOURNAL OF THE AMERICAN CHEMICAL SO- CIETY, vol. 93, nr. 15, July 1971, pages 3833-3834; Washington, US W. OPPOLZER: "Intramolecular cycloadditions of o- quinodimethanes." CHEMICAL ABSTRACTS, vol. 90, nr. 7, Feb- ruary 12, 1979, page 107, ref. nr.49009g; Co- lumbus, Ohio, US E.G.DELEGAN et al.: "Antimicrobial activity of some 5-R-3-alkenyl-2-thiohydantoins and products of their cyclization." CHEMICAL ABSTRACTS, vol. 78, nr. 25, June 25, 1973, page 408, ref. nr.159509e; Colum- bus, Ohio, US T.A. KRASNITSKAYA et al.: "Cyclization of substituded N- allylpseudothiohydantoins and N- allylpseudothiohydantoic acids." JOURNAL OF THE CHEMICAL SOCIETY PER- KIN J. 1980, pages 2383-2388; London, GB Md, GIASUDDIN AHMED et al.: "Enamine chemistry. Part 27. The effect of additional alpha- and beta-hetero-atoms on the ppi- conjugation and reactivity of enamines. Sub- or super-enamines?" CHEMICAL ABSTRACTS, vol. 98, nr. 5, Janu- ary 31, 1983, page 638, ref. nr. 34457t; Colum- bus, Ohio, US E. SCHMITZ et al.: "Synthesis of heterocyclic compounds by carbon- carbon bond closure. IV. Synthesis of heterocyclic compounds by intramolecular diene reaction." CHEMICAL ABSTRACTS, VOL. 101, NR. 15, OCTOBER 8, 1984, PAGE 685, REF. NR. 130435K; COLUMBUS, OHIO, US EP 0 128 006 B1 Description The present invention relates to a 2-cycloalkenylamine derivative and its salt which are soil disease- controlling agents, and production thereof. The 2-cycloalkenylamine derivative and its salt which are the 5 active ingredient of the present invention, have excellent controlling effect against soil diseases caused by plant pathogens. More particularly, the present invention relates to a soil disease-controlling agent contain- ing as an active ingredient a 2-cycloalkenylamine derivative or its salt (hereinafter referred to as present compound), a novel 2-cycloalkenylamine derivative and its salt, and production thereof, said 2-cycloal- kenylamine derivative being represented by the formula (I), 10 ^Vn / XR2 75 wherein R1 represents a hydrogen atom, a hydroxy, amino, lower cycloalkyl, lower cycloalkenyl, lower alkynyl, tetrahydrofurfuryl, piperidyl, arylthio, arylcarbonyloxy or aryl group, a lower alkyl group which may 20 be substituted with a halogen atom or a cyano, nitro, hydroxy, lower alkoxy, lower cycloalkyl, aryl, carboxy, lower alkoxycarbonyl, lower alkenyloxycarbonyl, aryloxycarbonyl, lower alkylcarbonyl or dialkylamino group, a lower alkenyl group which may be substituted with a halogen atom or an aryl group, or a lower alkoxyl group which may be substituted with an aryl group, R2 represents a hydrogen atom, a hydroxy, amino, lower cycloalkyl, lower cycloalkenyl, lower alkynyl, tetrahydrofurfuryl, piperidyl, arylthio, arylcarbonyloxy or 25 aryl group, a lower alkyl group which may be substituted with a halogen atom or a cyano, nitro, hydroxy, lower alkoxy, lower cycloalkyl, aryl, carboxy, lower alkoxycarbonyl, lower alkenyloxycarbonyl, aryloxycar- bonyl, lower alkylcarbonyl or dialkylamino group a lower alkenyl group which may be substituted with a halogen atom or an aryl group, a lower alkoxyl group which may be substituted with an aryl group, or a group represented by the formula, 30 -C-R3 II X 35 wherein R3 represents a hydrogen atom, a lower alkynyl, cycloalkyl, cycloalkenyl, aryl, lower alkyl- substituted oxathiinyl, uracilyl, arylcarbonyl or benzdioxanyl group, an alkyl group which may be substituted with a halogen atom or a lower alkoxy, cycloalkoxy, aryl, aryloxy, arylthio, cyano, carboxy or lower alkoxycarbonyl group, or a lower alkenyl group which may be substituted with a halogen atom or a carboxy 40 lower alkoxy or alkoxycarbonyl group, and X represents an oxygen or sulfur atom or an imino group, or R3 and R1, taken together, may form a lower alkylene or o-phenylene group, or R1 and R2, taken together, may form an alkylene or alkenylene group which may contain an oxygen or sulfur atom, a carbonyl group or an imino group or at least one of substituents, a group represented by the formula, 45 -c - z - c- II II X Y so wherein X and Y, which may be the same or different, represent an oxygen or sulfur atom or an imino group, and Z represents a cycloalkylene, cycloalkenylene, bicycloalkylene or arylene group, a lower alkylene group which may be substituted with a hydroxy, lower alkoxy, aryl, lower alkylcarbonyloxy, methylene,
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