Au 200075146 (12) Nach Dem Vertrag Tiber Die Internationale Zusammenarbeit Auf Dem Gebiet Des Patentwesens (Pct) Ver0ffentlichte Internationale Anmeldung
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AU 200075146 (12) NACH DEM VERTRAG TIBER DIE INTERNATIONALE ZUSAMMENARBEIT AUF DEM GEBIET DES PATENTWESENS (PCT) VER0FFENTLICHTE INTERNATIONALE ANMELDUNG (19) Weltorganisation fiir geistiges Eigen turn Internationales Biiro iwmiiinuiiffliiuinonnniinHniiai (43) Internationales Veroffentlichungsdatum (10) Internationale Veroflentlichungsnummer 15. M3rz 2001 (15.03.2001) PCT WO 01/17973 A3 (SI) Internationale Patentklassifikation7: C07D 498/04, (81) Bestimmungsstaaten (national): AE, AG, AL, AM, AT, 487/04, 231/32, C07C 69/616, 323/62, 69/734, 69/65, AU, AZ, BA, BB, BG, BR, BY, BZ, CA CH, CN, CR, CU, A01N 43/90 // (C07D 498/04, 273:00, 231:00) (C07D CZ, DE, DK, DM, DZ, EE, ES, Fl, GB, GD, GE, GH, GM, 487/04,273:00,231:00) (C07D 487/04,243:00, 231:00) HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, (21) Internationales Aktenzeichen: PCT/EP00/08657 MZ, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TI, TM, TR, TT, TZ, UA, UG, US, UZ, VN, YU, ZA, ZW. (22) Internationales Anmeldedatutn: (84) Bestimmungsstaaten (regional): ARIPO-Patent (GH, 5. September 2000 (05.09.2000) GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZW), eura- sisches Patent (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (25) Einreichungssprache: Deutsch europaisches Patent (AT, BE, CH, CY, DE, DK, ES, H, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE), OAPI-Patent (26) Veroffentlichungssprache: Deutsch (BF, BJ, CF, CG, CI, CM, GA, GN, GW, ML, MR, NE, SN, TD, TG). (30) Angaben zur PrioritSt: Veroffentlicht: 1644/99 7. September 1999 (07.09.1999) CH Mil intemationalem Recherchenbericht. — Vor Ablauf der fiir Anderungen der Anspriiche geltenden (71) Anmelder (fiir alle Bestimmungsstaaten mitAusnahme von Frist; Verbffentlichung wird wiederholt, falls Anderungen US): SYNGENTA PARTICIPATIONS AG [CH/CHJ; eintreffen. ssg Schwarzwaldallee 215, CH-4058 Basel (CH). (88) VerSffentlichungsdatum des internationalen (72) Erfinder; und Recherchenberichts: 10. Mai 2001 ■—— (75) Erfinder/Anmelder (nur fiir US): MAETZKE, Thomas = [CH/CHJ; Wilhelm-Haas-Weg 12, CH-4142 Miinchenstein Zur Erkliirung der Zweibuchstaben-Codes, und der anderen (CH). W END E BORN, Sebastian [DE/CHJ; KapeUen- AbkHrzungen yvird auf die Ertdarungen ("Guidance Notes on === weg 11, CH-4102 Binningen (CH). STOLLER, Andri Codes and Abbreviations") am Anfangjeder reguliiren Ausgabe === [CH/FRJ; 7, rue Charles Wolf, F-68730 Blotzheim (FR). der PCT-Gazette verwiesen. (54) Title: NOVEL HERBICIDES (54) Bezeichnung: NEUE HERBIZIDE A3 (57) Abstract: The invention relates to compounds of formula (I), wherein the substituents have the meaning cited in Claim (1). Said compounds are suitable for utilization as herbicides. (57) Zusatnmenfassung: Verbindungen 01/17973 der Formel G),worin die Substituenten die in Anspruch (1) angegebenen Bedeutungen besitzen, eignen sich zur WO Verwendung als Herbizide. PH/5-31143A - 1 - Novel herbicides The present invention relates to novel, herbicidally active pyrazolinone derivatives, to a process for their preparation, to compositions comprising such compounds, and to the use thereof in controlling weeds, especially in crops of useful plants, or in inhibiting plant growth. Pyrazolinone derivatives having herbicidal action are described, for example, in WO92/16510 and WO96/21652. Novel 4-arylpyrazolinones having herbicidal and growth-inhibiting properties have now been found. The present invention accordingly relates to compounds of formula I FL Q R. G wherein Rt and R3 are each independently of the other hydrogen, halogen, nitro, cyano, C1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, triiC^C^IkylsilyD-C^C^ikynyl, CrC^aloalkyl, C2-C6haloalkenyl, C3-C6cycloalkyl, halo-substituted C3-C6cycloalkyl, benzyl, C2-C6alkoxyalkyl, C2-C6alkylthio alkyl, hydroxy, mercapto, Ο,-Cgalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C4alkyl- carbonyl, C1-C4alkoxycarbonyl, Ci-C4alkylthio, C.|-C4alkylsulfinyl, C1-C4alkylsulfonyl, amino, CrC^lkylamino, diiCrC^lkyDamino, C1-C4hydroxyalkyl, formyl, Ci-C4alkylcarbonylamino or CrC^alkylsulfonylamino, R2 is phenyl, naphthyl or a 5- or 6-membered aromatic ring that may contain 1 or 2 hetero atoms selected from the group nitrogen, oxygen and sulfur, it being possible for the phenyl ring, the naphthyl ring and the 5- or 6-membered aromatic ring to be substituted by halogen, PH/5-31143A C3-C8cycloalkyl, hydroxy, mercapto, amino, amino-C^Cgalkyl, carboxyl-CrCealkyl, cyano, nitro or by formyl; and/or for the phenyl ring, the naphthyl ring and the 5- or 6-membered aromatic ring to be substituted by CrCealkyl, C^Cgalkoxy, hydroxy-Q-Cgalkyl, CpCgalkoxy-C^Cgalkyl, C^-Cg- alkoxy-CrCealkoxy, CrCealkylcarbonyl, CrCealkylthio, Q-Cgalkylsulfinyl, C^Cgalkylsulfonyl, mono-CrCealkylamino, di-CrCealkylamino, CrCgalkylcarbonylamino, CrCgalkylcarbonyl- (CrCealkyDamino, C2-C6alkenyl, C3-C6alkenyloxy, hydroxy-C3-C6alkenyl, C1-C6alkoxy-C3-C6- alkenyl, C1-C6alkoxy-C3-C6alkenyloxy, C2-C6alkenylcarbonyl, C2-C6alkenylthio, C2-C6alkenyl- sulfinyl, C2-C6alkenylsulfonyl, mono- or di-C2-C6alkenylamino, CpCgalkyi-CCg-Cgalkeny!)- amino, C2-C6alkenylcarbonylamino, C^Cgalkenylcarbonyl-fC^CgalkyDamino, C2-C6alkynyl, C3-C6alkynyloxy, hydroxy-C3-C6alkynyl, CrCealkoxy-Cg-Cealkynyl, C^Cgalkoxy-C^Cg- alkynyloxy, C2-C6alkynylcarbonyl, C2-C6alkynylthio, C2-C6alkynylsulfinyl, C2-C6alkynylsulfonyl, mono- or di-C3-C6alkynylamino, CrCealkyl-iCg-CgalkynyDamino, C2-C6alkynylcarbonylamino or by Cg-Cealkynylcarbonyl-iCi-CealkyDamino; and/or for the phenyl ring, the naphthyl ring and the 5- or 6-membered aromatic ring to be substituted by halo-substituted CrCealkyl, halo-substituted C^-Cgalkoxy, halo-substituted hydroxy-C^Cgalkyl, halo-substituted Q-Cgalkoxy-C^-Cgalkyl, halo-substituted CpCgalkoxy- C^Cgalkoxy, halo-substituted C^Cgalkylcarbonyl, halo-substituted CrCgalkylthio, halo- substituted CpCgalkylsulfinyl, halo-substituted C^Cgalkylsulfonyl, halo-substituted mono- Cj-Cgalkylamino, halo-substituted di-C^Cgalkylamino, halo-substituted C^Cgaikylcarbonyl- amino, halo-substituted C^Cgalkylcarbonyl-iCrCgalkyDamino, halo-substituted C2-C6alkenyl, halo-substituted C3-C6alkenyloxy, halo-substituted hydroxy-C3-C6alkenyl, halo-substituted CrCgalkoxy-Cg-Cgalkenyl, halo-substituted C^Cgalkoxy-Cg-Cgalkenyloxy, halo-substituted C2-C6alkenylcarbonyl, halo-substituted C2-C6alkenylthio, halo-substituted C2-C6alkenylsulfinyl, halo-substituted C2-C6alkenylsulfonyl, halo-substituted mono- or di-C3-C6alkenylamino, halo- substituted C^Cgalkyl-iCg-CgalkenyDamino, halo-substituted C2-C6alkenylcarbonylamino, halo-substituted C^-Cealkenylcarbonyl-iCrCealkyDamino, halo-substituted C2-C6alkynyl, halo- substituted C3-C6alkynyloxy, halo-substituted hydroxy-C3-C6alkynyl, halo-substituted CrC6- alkoxy-C3-C6alkynyl, halo-substituted C^Cgalkoxy-C^Cgalkynyloxy, halo-substituted C2-C6- alkynylcarbonyl, halo-substituted C2-C6alkynylthio, halo-substituted C2-C6alkynylsulfinyl, halo- substituted C2-C6alkynylsulfonyl, halo-substituted mono- or di-C3-C6alkynylamino, halo- substituted C^Cgalkyl-CCg-CgalkynyDamino, halo-substituted C2-C6alkynylcarbonylamino or by halo-substituted Ca-Cgalkynylcarbonyl-CCrCgalkyDamino; and/or PH/5-31143A for the phenyl ring, the naphthyl ring and the 5- or 6-membered aromatic ring to be substituted by a radical of formula COOR50, CONR51) SO2NR53R54or SO2OR55, wherein R50 R5i R52. R53 R54and R55are each independently of the others hydrogen, CrC6alkyl, C2-C6- alkenyl or C3-C6alkynyl, or CrC6alkyl, C2-C6alkenyl or C3-C6alkynyl each substituted by halogen, hydroxy, alkoxy, mercapto, amino, cyano, nitro, alkylthio, alkylsulfinyl or by alkylsulfonyl, R4 and R5 are each independently of the other hydrogen, Ο,-C^alkyl, CrC12haloalkyl, CrC12- hydroxyalkyl, C3-C8alkenyl, C3-C8alkynyl, CrC10alkoxy-CrC8alkyl, or C3-C8alkyl that may contain one or two oxygen atoms, CrC10alkylthio-CrC8alkyl, C3-C8cycloalkyl, C3-C8cyclo- alkyl that contains 1 or 2 hetero atoms selected from the group oxygen and sulfur, C3-C8- halocycloalkyl, C3-C8halocycloalkyl that contains 1 or 2 hetero atoms selected from the group oxygen and sulfur, phenyl, or phenyl substituted by halogen, CrCealkyl, CrC6haloalkyl, CrC6alkoxy, CrC6haloalkoxy, nitro or by cyano, or R4 and R5 are each independently of the other a 5- or 6-membered ring that may contain hetero atoms selected from the group oxygen, sulfur and nitrogen, or R4 and R5, together with the atoms to which they are bonded, form a 5- to 8-membered ring, which may contain 1 or 2 oxygen atoms, sulfur atoms or NR6 groups, wherein R6 is hydrogen, CrC4alkyl, CrC6alkylcarbonyl, CrC6alkylsulfonyl, C3-C6alkenyl or C3-C6- alkynyl, and which may be substituted by halogen, hydroxy, CrC10alkyl, C1-C10alkoxy, Ο,-Qohaloalkyl, C3-C8cycloalkyl, phenyl or by benzyl; or which may be substituted by phenyl substituted by halogen, CrCealkyl, CrC6haloalkyl, C3-C6cycloalkyl, hydroxy, CrC6alkoxy, CrC6alkoxy-CrC6alkoxy, CrC6haloalkoxy or by nitro, or by benzyl substituted by halogen, CrCealkyl, CrC6haloalkyl, C3-C6cycloalkyl, hydroxy, CrC6alkoxy, CrC6haloalkoxy or by nitro; or which may be substituted by CH2-heteroaryl, wherein the aryl moiety has 5 or 6 members, or by halo-, CrC6alkyl-, CrCehaloalkyl-, CrC6cycloalkyl-, hydroxy-, CrC6alkoxy-, CrC6halo- alkoxy- or nitro-substituted CH2-heteroaryl, wherein the aryl moiety has 5 or 6 members; or which may be substituted by heteroaryl, wherein the aryl moiety has 5 or 6 members, or by halo-, CrC6alkyl-, CrCehaloalkyl-, hydroxy-, CrC6alkoxy-, CrC6haloalkoxy-, cycloalkyl- or nitro-substituted heteroaryl, wherein the aryl moiety has 5 or 6 members; and PH/5-31143A which