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United States Patent (19) 11 Patent Number: 5,945,382 Cantegrill Et Al

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United States Patent (19) 11 Patent Number: 5,945,382 Cantegrill Et Al US005.945382A United States Patent (19) 11 Patent Number: 5,945,382 Cantegrill et al. (45) Date of Patent: *Aug. 31, 1999 54 FUNGICIDAL ARYLPYRAZOLES 2300173 12/1990 Japan. 2224208 5/1990 United Kingdom. 75 Inventors: Richard Cantegril, Lyons; Denis Croisat, Paris; Philippe Desbordes, OTHER PUBLICATIONS Lyons, Francois Guigues, English translation of JP 2-300173, 1990. Rillieux-la-Pape; Jacques Mortier, La English translation of JP 59–53468, 1984. Bouéxier; Raymond Peignier, Caluire; English translation of JP 3-93774, 1991. Jean Pierre Vors, Lyons, all of France Miura et al., (CA 1.14:164226), 1991. Miura et al., (CA 115:92260), 1991. 73 Assignee: Rhone-Poulenc Agrochimie, Lyons, Chemical Abstracts, vol. 108, No. 23, 1986, abstract No. France 204577b. CAS Registry Handbook, No. section, RN=114913-44-9, * Notice: This patent is subject to a terminal dis 114486-01-0, 99067-15-9, 113140-19-5, 73227-97-1, claimer. 27069-17-6, 18099-21–3, 17978-27-7, 1988. 21 Appl. No.: 08/325,283 Hattori et al., CA 68:68981 (1968), Registry No. 17978–25–5, 17978-26-6, 17978-27-7 and 18099–21-3. 22 PCT Filed: Apr. 26, 1993 Hattori et al., CA 68:68982 (1968), Registry No. 17978-28-8. 86 PCT No.: PCT/FR93/00403 Janssen et al., CA 78: 159514 (1973), Registry No. S371 Date: Dec. 22, 1994 38858-97-8 and 38859-02-8. Chang et al., CA 92:146667 (1980), Registry No. S 102(e) Date: Dec. 22, 1994 73227 91-1. Berenyi et al., CA 94:156963 (1981), Registry No. 87 PCT Pub. No.: WO93/22287 771.97-10-5. PCT Pub. Date: Nov. 11, 1993 Markwell et al., CA 108:112444 (1988), Registry No. 113140-19-5. 30 Foreign Application Priority Data Maslova et al., CA 119:8733 (1993), Registry No. Apr. 27, 1992 FR France ................................... 92 O5434 147993-04-2. 51) Int. Cl. ........................ A01N 43/56; A61K 31/415; Maslova et al., Khim. Farm. Zh. (1992), 26(11–12), pp. CO7D 231/12 77-81, Registry No. 147993–04–2. 52 U.S. Cl. ........................ 504/280; 514/406; 548/377.1 Primary Examiner-Laura L. Stockton 58 Field of Search ......................... 548/377.1; 514/406; Attorney, Agent, or Firm-Burns, Doane, Swecker & 504/280 Mathis, L.L.P. 56) References Cited 57 ABSTRACT The present invention relates to new derivatives of the U.S. PATENT DOCUMENTS family of 3-arylpyrazoles of formula (I), their methods of 2,721,143 10/1955 Kraft et al. ............................... 99/222 preparation, the compositions containing them and their 2.946,765 7/1960 Roos et al..... 548/377.1 utilization for the protection of plants against fungal dis 3,072,525 1/1963 Neumann .................................. 167/31 CSCS. 3,658,838 4/1972 Kiehne et al. ... ... 260/310 R 4,008,249 2/1977 Fischer et al. ... ... 548/377.1 (I) 4,055,409 10/1977 Johnson et al... 548/377.1 4,072,498 2/1978 Moon et al. ................................ 71/92 4,477,462 10/1984 Aoyagi ............. 424/273 P 4,792,565 12/1988 Shimotori et al. ... ... 514/406 5,134,142 7/1992 Matsuo et al. ... ... 514/255 5,342,835 8/1994 Pepin et al. ... 514/227.5 5,523,280 6/1996 Chene et al... ... 504/280 5,663,119 9/1997 Chene et al. ............................ 504/280 FOREIGN PATENT DOCUMENTS 0360701 3/1990 European Pat. Off.. 1152109 8/1963 Germany. 42-11944 7/1967 Japan. 42-11945 7/1967 Japan. 59–53468 3/1984 Japan. 15 Claims, No Drawings 5,945,382 1 2 FUNGCIDALARYLPYRAZOLES nitrogen atom, it being possible for the carbons of this bridge to be unsubstituted or substituted by at least one This application is a 371 of PCT/FR93/00403 filed Apr. halogen atom and/or at least one hydroxyl, alkoxy, 26, 1993. alkylthio, mono- or dialylamino, or alkylsulphinyl or The present invention relates to new derivatives of the -Sulphonyl group, the alkyl part being as defined above, 3-arylpyrazole family, to the processes for their preparation, Z is: to the compositions containing them and to their use for a hydrogen or halogen atom or a cyano, nitro or hydroxyl protecting plants against fungal diseases. group or More specifically, the subject of the invention is alkyl, haloalkyl, cycloalkyl or cycloalkylalkyl, it being 3-arylpyrazole derivatives, characterised in that they are of possible for the cycloalkyl part to be substituted by the formula I: group GR, defined below, or alkoxy, optionally Substituted by a hydroxyl, an alkoxy or an alkylthio; or an alkylthio, a phenyloxy or phenylthio, 15 an amino optionally Substituted by one or two alkyls or optionally Substituted alkenyl or alkynyl, each containing from 3 to 7 carbon atoms optionally substituted phenyl or Het, a group of formula C(Z)Z in which: Z is an oxygen or Sulphur atom or an alkylamino or imino or arylamino group and Z2 is: a hydrogen or halogen atom or a hydroxyl, thiol, cyano or amino group, in which: 25 alkyl, alkoxy or alkylthio, X, X, X, X and Xs, which are identical or different, alkenyl or alkynyl, each containing from 3 to 7 C. carbon atoms a hydrogen or halogen atom, or a hydroxyl, cyano, phenyl, phenylalkyl, phenoxy, phenalkyloxy, thiocyanato, nitro, nitroSO or amino group, the amino Het or Het-alkyl, group optionally being Substituted by one or two alkyls phenylalkenyl or phenylalkynyl; Het-alkenyl or Het or phenyls, alkynyl an alkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, mono- or dialkylamino, or a mono- or diphenyl alkylsulphinylalkyl, alkylsulphonylalkyl, benzyl, amino or alkenyl, alkynyl, cyanoalkyl, alkoxy, alkenoxy, Sulphonylamino radical, alkylthio, formyl, acetyl, alkylcarbonyl, alkoxy(thio) 35 a phosphoryl group Substituted by two radicals chosen carbonyl, mono- or dialkylamino(thio)carbonyl, from the group comprising alkyl, alkoxy, alkylthio, iminocarbonyl, mono- or diarylamino(thio)carbonyl, dialkylamino, cycloalkyl or cycloalkylalkyl, alkenyl carboxyl, carboxylate, carbamoyl or benzoyl radical, or alkynyl, phenyl, phenylalkyl, Het or Het-alkyl, a phenyl, phenyloxy or phenylthio radical, phenyl or Het, optionally Substituted; 40 or a group S(Z)(Z)Z, in which Z and Z have the an alkyl- or alkoxy- or monoalkylamino- or dialkylamino Same meanings as above and Z has the same mean or phenylsulphenyl or -Sulphinyl or -Sulphonyl, ings. Without necessarily being equal to Z, a phosphoryl group, Substituted by two groups chosen from the group comprising alkyl, alkoxy, alkylthio and with the proviso that Z is not a hydrogen atom when X, dialkylamino, benzyloxy, phenyloxy or phenyl, 45 X and Xs are each a hydrogen atom; and the tautomeric forms of formula Ia, when Z is a a trialkylsilyl or alkylphenylsilyl group, hydrogen atom or a group of formula C(Z)Z, or S(Z) Two of the adjacent X, X2, X, X and Xs groups can also be connected to each other via a carbon bridge com prising 2 to 4 members, one at least of which can be replaced by an oxygen, Sulphur or nitrogen atom, it being possible for 50 Ia the carbons of this bridge to be unsubstituted or substituted by at least one halogen atom and/or at least one hydroxyl, amino, alkyl, alkoxy, alkylthio, mono- or dialylamino, or alkylsulphinyl or -Sulphonyl group, the alkyl part being as defined above, 55 with the proviso that X to Xs and X to Xs cannot be each Simultaneously a hydrogen atom; X and Y is a hydrogen or halogen atom or a nitro, nitrile, thiocyanato or alkyl, alkoxy or alkylthio, or alkylsul 60 phinyl or alkylsulphonyl group, the alkyl part of these their hydracid or perchloric or nitric or Sulphuric acid radicals being optionally mono- or polyhalogenated, or or alkyl- or (optionally Substituted)phenylsulphonic an amino optionally Substituted by one or two alkyls or acid Salts and their metal or metalloid complexes, phenyls, it being understood that in all the meanings above, Y and X or Xs can also be connected to each other via 65 the hydrocarbon part of these groups can comprise a carbon bridge comprising 5 to 7 members, one at least from 1 to 7 carbon atoms and can be optionally of which can be replaced by an oxygen, Sulphur or halogenated (from 1 to 8 halogen atoms), 5,945,382 3 4 the cycloalkyl part of these groups can comprise from pages 239 to 241 and 263, Pergamon Press; “Advances in 3 to 7 carbon atoms and can be optionally substituted Heterocyclic Chemistry”, A. N. Kost and I. I. Grandberg, by at least one Substituent chosen from the group 1966, Vol. 6, pages 391 to 396, Academic Press and “The GR, Chemistry of Heterocyclic Compounds’, L. C. Behr, R. the phenyl part denotes the phenyl ring optionally Fusco and C. H. Jardoe, 1967, J. Wiley & Sons. substituted by 1 to 5 substituents chosen from the A first process for the manufacture of the compounds of group comprising a halogen atom or an alkyl or alkoxy containing 1 to 3 carbon atoms, formula II, in which Z is a hydrogen atom and Y is a halogen Het is a mono- or bicyclic heterocyclic radical contain atom, consists in reacting a 3-arylpyrazole of formula III: ing from 5 to 10 atoms, 1 to 4 of which are heteroa toms (oxygen, Sulphur, nitrogen or phosphorus). 1O Preferably, in the formula, Y is a chlorine or bromine atOm. Other preferred derivatives are such that, in the formula I, Z is a hydrogen or a group C(Z)Z, in which Z is an oxygen or Sulphur atom. 15 Other preferred derivatives are such that, in the formula I, X, X and X are a hydrogen or halogen atom or a nitro group or an optionally halogenated alkyl group containing 1 to 4 carbon atoms.
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