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WO1999040090A1 - Derives de la pyridine fusionnes avec un azole, et herbicide - Google Patents

Derives de la pyridine fusionnes avec un azole, et herbicide Download PDF

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Publication number
WO1999040090A1
WO1999040090A1 PCT/JP1999/000451 JP9900451W WO9940090A1 WO 1999040090 A1 WO1999040090 A1 WO 1999040090A1 JP 9900451 W JP9900451 W JP 9900451W WO 9940090 A1 WO9940090 A1 WO 9940090A1
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Prior art keywords
group
alkyl
same meaning
alkoxy
substituted phenyl
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PCT/JP1999/000451
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English (en)
Japanese (ja)
Inventor
Yoshihiro Kudo
Jun Satow
Shigeomi Watanabe
Tooru Ohki
Chiaki Kawaguchi
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Nissan Chemical Industries, Ltd.
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Application filed by Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU22985/99A priority Critical patent/AU2298599A/en
Publication of WO1999040090A1 publication Critical patent/WO1999040090A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to a novel azole condensed pyridine derivative and a herbicide containing the same as an active ingredient.
  • the present inventors have conducted intensive studies on the herbicidal action of the novel azole condensed pyridin derivative, and as a result, have found that the compound of the present invention represented by the following formula has an excellent herbicidal action.
  • the invention has been completed. That is, the present invention relates to the formula (1)
  • R f represents a C! — ⁇ 4 haloalkyl group
  • X is a hydrogen atom, a halo gen atom, Shiano group, ⁇ 1 - ⁇ 4 Arukiru group,
  • Y represents a hydrogen atom, a C i -C 4 alkyl group or a halogen atom
  • Z 1 Z 2 —
  • R a and R b are each independent a hydrogen atom, one C 4 alkyl group, human mud Kishime Chi group, main Luke flop Conclusion methyl group, a hydroxyl group, two collected by filtration group, A Mi amino group, main Luke blanking preparative group, main Chirume Luke flop DOO It represents C 4 Ashiru group, ⁇ 4 Nono Roarukiru group, an C 4 alkoxycarbonyl group or a halogen atom), - group, formate group, a carboxyl group, meta Nsuruhoniru group, C!. 0
  • N NC (Ra) (Ra represents the same meaning as described above),
  • N N N or
  • C (R a) C (R b) C (R c) (R a and R b have the same meanings as described above, and R c is a hydrogen atom, a C 1 -C 4 alkyl group or a halogen atom. Represents.), Represents,
  • R 1 represents a hydrogen atom or a halogen atom
  • R 2 represents a hydrogen atom or a halogen atom
  • R 3 is a hydrogen atom, a nitrogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, an amino group, a formyl group, a carboxyl group, a cyanomethyl group, C i-C 4 alkoxycarbonyl group, Sulf Amoi group, Chiokarubamoi group, force Rubamoi group, 0 1 - 0 4 Arukiru group, one C 4 alkoxy group, C l-C 4 haloalkyl group, C -! C 4 halo A Alkoxy group, monoalkylthio group, Ci-alkylsulfonyl group, ⁇ !
  • - ⁇ 4alkyl) 2amino group phenyl group, P-cyclophenyl group, benzoyl group, p-k (B) benzoyl group, benzoyloxy group, p — benzoyloxy group, benzyl group, p — methylbenzyl group, p — benzyl group, benzenesulfonyl group, p Black benzenesulfonyl group, Ci-C4 alkoxycarbonyloxy group,
  • I 0 _ Q-substituted phenyl group (Q may be saturated or unsaturated, branched, and may be substituted with a halogen atom, a cyano group or a C! -C4 alkoxycarbonyl group. It represents a good C 6 alkylene chain, and “substituted phenyl” is a halogen atom, a cyano group, a nitro group, an amino group, a carboxyl group, a hydroxy group, a C 1, 1C 4 alkyl groups,
  • C _ Represents a phenyl group which may be optionally substituted by an alkoxycarbonyl group.
  • R 4 is a hydrogen atom, a hydrogen atom, a hydrogen atom, a hydroxymethyl group, a formylamino group, a formyl group, a carboxyl group, a carnomoyl group, a cyano group, a sulfo group, a chlorosulfonyl group , Mercapto group, hydroxy group, amino group, nitro group, hydrazino group, ureido group, phenyl group, 1,3-dioxolan 1-2-yl group, 1,3 - Jiokisan one 2 - I le group, C -! C 8 alkyl group, C 3 - ⁇ 8 a cycloalkyl group, C 3 - C 8 alkenyl group, C 3 - C 8 alkynyl group,
  • R 1 1 is a C! -C 8 alkyl group, C 3 -C 8 cycloal C 3 —c 8 alkenyl, c 3 —c 8 alkynyl, c 3 —c cycloalkyl (C! —C 4) alkyl, C i —C 8 haloalkyl, C 3 —C 8 , Alkenyl, C 3 -C 8 , alkynyl, 4 -butanol 2 -yl, 5 -pentanol 2 -yl, 6 -hexanolide 2 —Il group, C! One C 4 alkoxycarbonyl group,
  • Substituted phenylalanine (c 3 - c 8) alkynyl groups, (substituted phenylalanine represents the meaning of the same way.)
  • Shiano C -! C alkyl group, C, - alkoxy (C i- C alkyl group, C, one C 4 alkylthio (C t- c 4) alkyl group, Ben Jiruoki caulking methyl group, Te door La arsenide mud Villa group, Okishiraniru group, Okishira Nirume ethyl group, Te preparative La inhibit mud off Ranil groups, c, - c 8 Ashiru group, Shiano (C 3 - C 8) alkenyl or C, - represents a C haloacyl group). ,
  • Trifluorometyl 3 Kuro mouth 1 2 — pyriyloxy group.
  • Alkyl) 2 Amino group, C i-I »alkylidene mino group, phenyl group, benzyl group, C3-C8 alkenyloxycarbonyl (C ! —C 4) alkyl group, C 3 —C 8 alkynyloxycarbonyl (C, C 4) alkyl group, or C i—C 4 alkoxycarbonyl (C ⁇ —C 4) alkyl group You. ),
  • R 12 has the same meaning as described above, and 113 is a ⁇ 1 — ⁇ 8 alkyl group, a C 3 — C 8 alkenyl group, a C 3 — C 8 R 12 and R 13 each represent an alkynyl group or a 3- to 8-membered hetero ring which may be substituted by a C 4 alkyl group including itself, and
  • the constituent elements are arbitrarily selected from carbon, oxygen, hydrogen, sulfur and nitrogen atoms.
  • R14 represents a Ci-alkyl group or a C! -Chaloalkyl group
  • R 1 5 is C, - C 8 alkyl group, C, -. C, mouth alkyl group, C 3 - C 8 a cycloalkyl group, C 3 - C 8 alkenyl group, C 3- C 8 represents an alkynyl group, a benzyl group or a phenyl group), one N (S02R15) 2 (R15 has the same meaning as described above), -N (R16) S 02 R 1 5 (R 1 5 is Table Wa as defined above, 1 1 6 ⁇ 1 - ⁇ 6 Arukiru groups, C 3 - C 8 alkenyl groups, C 3 - ⁇ 8 ⁇ Rukiniru groups, C , One C 4 no, mouth alkyl group, C 3 —C P nodroalkenyl group,
  • R 1 7 (R 1 7 is C -! C 6 alkyl group, C 3 - C 8 an alkenyl group, C 3 - C 8 alkynyl group, one C 4 haloalkyl group, full et alkenyl group or a substituted benzyl group (Ci-C4 alkyl group, C ⁇ —C4 alkyl Coxy group, nitrogen atom, C! One C haloalkyl group, C i haloalkoxy group, C! — C Represents a benzyl group which may be arbitrarily substituted by an alkoxycarbonyl group, a nitro group or a cyano group. ).
  • R 5 is a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, an amino group, a carboxyl group, a mercapto group, a C 1 -C alkyl group, a C 3 -C alkenyl group, a C 3 -C 8 Alkynyl group, C, — C 4 alkoxy group, C
  • R 3 and R 4 or R 4 and R 5 are calculated from the formula (a) by (y)
  • R f, R a, R b, X, Y, R l, R 2, R 3 and R 5 represent the same meaning as described above,
  • R 28 and R 29 each independently represent a hydrogen atom, a cyano group, a halogen atom, a C i -C 6 alkyl group, a C 2 -C 8 alkenyl group, a C 2 -C 8 alkynyl group, a C! A C 4 haloalkyl group, a C!
  • R 3 0 is a hydrogen atom, C -! C 6 alkyl group, C -! C 6 haloalkyl group, C 2 —C 8 alkenyl group, C 2 —C 8 alkynyl group, C! —C 6 acyl group, C! — C 4 alkoxycarbonyl group or C!
  • C i-C 4 alkyl group and Table Wa
  • R 3 1 is hydrogen atom, a hydroxyl group, A Mi amino group, C i one C 8 alkyl group, C 3 - C 8 alkenyl group, C 3 - C 8 alkynyl group, ⁇ 1 over. 8 Haroarukiru group, ⁇ 3- C 8 Nono Russia alkenyl group, C 3- C 8 Nono Roarukiniru group, C -! C e Ashiru group, C i- C 6 Ha Roashiru group, formate group, Ben zone I Lumpur based on , full Enashiru group, C 3- C 8 a cycloalkyl (C i one C 4) alkyl group,
  • I Q-CN group (Q represents the same meaning as above) or I Q represents a substituted phenyl group (Q and substituted phenyl have the same meanings as described above);
  • R 3 2 represents a hydrogen atom, formate group, a carboxyl group, human de Rokishime Chi group, one C 6 alkyl group, C, _ C, mouth alkyl group, C, - ⁇ sill group, C -! C 4 alkoxy (C! —C alkyl group, C) -C4 alkylthio (C! —C4) alkyl group, C! -C4 alkylsulfonyl
  • R 33 represents a hydrogen atom, a halogen atom, a C i -C 6 alkyl group, a C i -C ⁇ alkoxycarbonyl group or a C 1 -C 4 acyl group;
  • R 34 represents a hydrogen atom, a halogen atom, a C! -C 6 alkyl group, a C 4 alkoxycarbonyl group or a C i -C 4 acyl group,
  • R 3 5 is a hydrogen atom, formate group, a carboxyl group, human mud Kishime Chi group, one C 6 alkyl groups, C i-C 6 haloalkyl groups, C one C 6 ⁇ sills groups, C -!! CA alkoxy (C! one C 4) alkyl group, C i-C 4 ⁇ alkylthio (C i- C 4) alkyl group, C i-C 4 alkylsulfonyl !
  • (C i-C 4) alkyl groups C one C 4 alkoxycarbonyl group, one C 0 NH - (C i- C alkyl) group, one CH (0 H) - (C , - C 4 ⁇ alkyl) group , - CH (0 H) - (C 2 - C 6 alkenyl) groups, - CH
  • R 36 is a hydrogen atom, a halogen atom, a C i -C 6 alkyl group, a C 6 -alkoxy group, a C! -C 6 -alkylthio group or a C! -C 4 -alkoxy group
  • (C 1 -C 4) represents an alkyl group
  • R 3 7 represents a hydrogen atom, a halogen atom, A Mi amino group, C -! C 6 alkyl group, C, one C e alkoxy group, C i-C 6 Arukiruchio group or C, - C 4 ⁇ alkoxy (C i — Represents a C alkyl group,
  • R 38 and R 39 each independently represent a hydrogen atom or a C! -C 6 alkyl group
  • R 40 is a hydrogen atom or C! — Represents a C 6 alkyl group
  • R 41 represents a C! —C 6 alkyl group
  • R 42 and R 43 each independently represent a C 6 alkyl group
  • R 44 represents a hydrogen atom, a C i —C 6 alkyl group, a C! —Ce acyl group, a C i —C 6 haloacyl group, C i-C 6 alkoxycarbonyl group, ⁇ 1 - ⁇ 6 ⁇ Le alkylsulfonyl group, C 1 - C 6 haloalkylsulfonyl group, or a C 1 one C 4 alkoxy (C i—C represents an alkyl group,
  • R 4 5 is hydrogen atom, C -! C 6 alkyl group, C -! C 4 haloalkyl group, human de proxy (C -! C 4) alkyl group or a C! One C 4 alkoxy (C
  • C) represents an alkyl group
  • R 46 is a hydrogen atom, a halogen atom, a C—C 6 alkyl group, a nitro group, an amino group, a cyano group, a formyl group, a C! —C 6 acyl group, a C—C haloacyl group , Carboxyl group, C! — C 4 alkoxycarbonyl group, hydroxy (C! —C alkyl group, C! —C 4 alkylthio group, 1 C 4 alkylsulfonyl group, C i—C 4 alkyl imino (C! 1 C alkyl group or Doxymino (Ci-C alkyl group;
  • R 47 is a hydrogen atom, a halogen atom, a C 6 alkyl group, a C! —C haloalkyl group, a C! —C 6 alkoxy group, a C 2 —C 8 alkenyl group,
  • R 48 is a hydrogen atom, a halogen atom, a C! —C 6 alkyl group, a C i—C 6 no, a mouth alkyl group, a C! —C c alkoxy group, a C 2 —C 8 alkenyl group, a C 2 —C 8 alkynyl, C 2 - C 3 Arukeniruokishi groups, C 2 - ⁇ 8 ⁇ Rukiniruokishi group, C i one C alkylthio group, C i one C alkoxy group, C 2 - C 8 alkenylthio group, C 2 - C 8 Arukiniruchi O group, C i-alkylamine Mi amino group, (C -! C 4 alkyl) 2 ⁇ Mi amino group c 2 - c 8 Arukenirua Mi amino group, c 2 - c 8 Arukinirua Mi amino group, c 2 - c 8 Ar
  • R 49 is a hydrogen atom, a halogen atom, a C, —C 6 alkyl group, a C, —C 6 haloalkyl group, a C, 1-C 6 alkoxy group, a C s -C 8 alkenyl group, a C 2 -C 8 alkynyl group , C 2 - C e Arukeniruokishi groups, C 2 - 0 8 ⁇ Rukiniruokishi group, C i-C 6 alkylthio group, one C 4 alkoxy carbonyl groups, c 2 - c 8 alkenylthio group, c 2 - c 8 Arukiniruchi O group, C i one alkylamine Mi amino group, (C i- C 4 alkyl) A Mi amino group, c 2 - ⁇ 8 Arukenirua Mi amino group, c 2 - c 8 Arukinirua Mi amino group, c 2 -
  • R 50 represents a hydrogen atom, a C! C 6 alkyl group, a C 2 -C 8 alkenyl group, a C 2 -C 8 alkynyl group, a phenyl group or a benzyl group
  • R 51 represents a hydrogen atom, a C i-C 6 alkyl group, C 3 —C 8 alkenyl group, c 3 —c 8 alkynyl group, c! —c 4 noloalkyl group, c 3 —c 8 noloalkenyl group, C 3 —C 8 no, mouth alkynyl group, Shiano (C i-C Al kill group, C -! C alkoxy (C -!
  • a novel azole condensed pyridin derivative hereinafter referred to as the compound of the present invention
  • a herbicide characterized by containing them as an active ingredient hereinafter referred to as the compound of the present invention
  • R f includes CF 3 , CF 2 C 1, CF 2 H, CFC 1 H, CF 3 CF 2 or CF 2 CF 2 C 1, preferably CF 3 No. Is an X H, C l, B r , F, I, CN, M e, E t, P r, iso - P r, CF, CFC 1, CH 2 C 1, CH 2 B r, CF 2 H
  • Pr NH-iso-Pr, N (Me) N (Et) N (Pr) or N (iso-Pr) 2 , preferably CI, Br
  • Y is H, Cl, Br, F, I, Me, Et, Pr, iso
  • Pr or Bu and preferably H.
  • R a or R b are each independently H, Cl, Br, F,
  • R c is H, Me, Et, Pr, F, Cl, Br or I.
  • R 1 includes H, C I, F, Br or I, preferably
  • R 2 includes H, C 1, F, Br or I, preferably
  • R 3 is a hydrogen atom, C I, F, Br, I, C ⁇ N, C S N H
  • R 28 is a hydrogen atom, F, Cl, Br, I, CN, Me, Et
  • R 2 9 and to a hydrogen atom, F, C l, B r , I, CN, M e, E t, P r, B u, iso P r, tert - B u, CHCH CH 2, CH 2 C ⁇ CH, CF, CHF, CH 2 F, OM e, ⁇ E t, OP r, C 0 2 M e, C 0 E t, C_ ⁇ 2 P r, C 0 2 - iso- P r, C_ ⁇ 2 Bu, Ph, 4 CI-Ph, 3 CI-Ph, 2-CI-Ph, 4-F-Ph, 3—F—Ph, 2—F—Ph, 4 Me—Ph, 3—Me—Ph, 2—Me_Ph, 4—MeO—Ph, 3—MeO—Ph or 2—Me0—Ph Is mentioned.
  • R 28 and R 29 are taken together as a carbonyl group, Mouth propyl, cyclobutyl, cyclohexyl or cyclopentyl.
  • R 33 is H, Cl, Br, F, I, Me, Et, Pr, iso—Pr, Bu, sec_Bu, iso—Bu, tert—Bu. ,
  • R34 is H, Cl, Br, F, I, Me, Et, Pr, iso-Pr, Bu, sec-Bu, iso-Bu, tert-Bu ,
  • R 38 is H, Cl, Br, F, I, NH 2 , Me, Et, Pr, so Pr, Bu, sec — Bu, iso — Bu, tert B u, Pn, neo-Pn or tert-Pn.
  • R 39 is H, Cl, Br, F, I, NH 2 , Me, Et, Pr, iso — Pr, Bu, sec — Bu, iso — Bu, tert — Bu, Pn, neo — Pn or tert — Pn.
  • R 40 is H, Me, Et, Pr, iso—Pr, Bu, sec—Bu, iso—Bu, tert—BuPn, neo—Pn or tert — Pn.
  • R 41 is Me, Et, Pr, iso—Pr, Bu, sec—Bu, iso—Bu, tert_Bu, Pn, neo—Pn or tert—P n.
  • R 42 is Me, Et, Pr, iso — Pr, Bu, sec
  • B u iso — B u, t e r t — B u, P n, n e o — P n or t e r t — P n
  • NHP r NH- iso - P r , NHCH 2 CH two CH 2, NHCHC three CH, N (M e) 2 , N (E t) 2, N (P r) 2, N (CHC
  • neo-P n CH 2 C (CH 3 )
  • the compound of the present invention can be synthesized, for example, by the method shown in Scheme 15 (X, Y, Z 1, Z 2, Z 3, R f, R 1 to R 5 in Schemes 1 to 5).
  • R ⁇ and R alk each independently represent a C 1 -C 4 alkyl group, and Ha 1 represents a halogen atom.
  • the keto acid ester derivative (2) and the phenylacetonitrile derivative (3) were converted to sodium hydride, potassium hydride, sodium methoxide, sodium hydride.
  • bases such as toxide, evening char, toxic oxide, potassium carbonate, sodium carbonate, caustic soda, caustic caliform, dimethylformamide (DMF), dimethylformamide (DMF) Thiacetamide (DMA), dimethyl sulfoxide (DMSO), tetranoid flank (THF;), 1, 3-dimethyl-2, imidazolinone (DMI), acetic acid React in an inert solvent such as tonitrile or toluene.
  • bases such as toxide, evening char, toxic oxide, potassium carbonate, sodium carbonate, caustic soda, caustic caliform, dimethylformamide (DMF), dimethylformamide (DMF) Thiacetamide (DMA), dimethyl sulfoxide (DMSO), tetranoid flank (THF;), 1, 3-d
  • 4—Hydroxy-3—phenyl —2—pyridone derivative (4) can be synthesized.
  • the compound (4) has a tautomeric relationship with the compound (4 ′), but is represented in the form of the compound (4) in the present patent.
  • Toamide dimethyl sulfoxide (DMSO), tetrahydrofuran flank (THF), 1,3-dimethyl 1-2-imidazolinonone (DMI), acetate
  • an inert solvent such as tonitrile or toluene, or without solvent
  • halogenating agent such as phosphorus oxychloride, phosphorus oxybromide, phosphorus pentachloride, phosphorus trichloride, thionyl chloride, or thionyl bromide and an inert solvent such as toluene or xylene, or no solvent
  • a halogenating agent such as phosphorus oxychloride, phosphorus oxybromide, phosphorus pentachloride, phosphorus trichloride, thionyl chloride, or thionyl bromide and an inert solvent such as toluene or xylene, or no solvent
  • tertiary amines such as getyl aniline, pyridine, triethylamine, etc.
  • the keto acid ester derivative (2) and the benzylazole derivative (6) were converted to sodium hydride, potassium hydride, sodium methoxide, In the presence or absence of bases such as sodium methoxide, sodium hydroxide, lithium carbonate, sodium carbonate, caustic soda, caustic california, etc.
  • DMF Dimethylformamide
  • DMA dimethylacetamide
  • DMSO dimethylsulfoxide
  • THF tetranodrofuran
  • an inert solvent such as linone (DMI), acetonitrile, or toluene, with or without a solvent to produce a hydroxyazol-condensed pyridine derivative (7). I can do it.
  • Compound (7) is reacted with a halogenating agent such as phosphorus oxychloride, phosphorus oxybromide, phosphorus pentachloride, phosphorus trichloride, thionyl chloride, or thionyl bromide in an inert solvent such as toluene or xylene.
  • a halogenating agent such as phosphorus oxychloride, phosphorus oxybromide, phosphorus pentachloride, phosphorus trichloride, thionyl chloride, or thionyl bromide
  • an inert solvent such as toluene or xylene.
  • Tertiary amines such as getylanilinine, pyridine, tritylamine, etc .
  • amides such as DMF
  • DMF Dimethylformamide
  • DMA dimethylacetamide
  • DMSO dimethylsulfoxide
  • THF tetranoid flank
  • DI 1, 3-dimethyl-2-a React in an inert solvent such as midazolinone (DMI), acetonitrile, or toluene.
  • the obtained intermediate was isolated or purified as it was, without being subjected to acetic acid, propionic acid, trifluoroacetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, methansulphonic acid, trifluoromethansulphonic acid,
  • an acid such as p-toluenesulfonic acid
  • the ring is closed with ammonia or ammonium acetate and an inert solvent such as toluene, xylene, or water, or without a solvent.
  • An enylpyridin derivative (9) can be synthesized.
  • the compound (9) has a tautomeric relationship with the compound (9 '), but is expressed in the form of the compound (9) in this patent.
  • the compound (11) is in a tautomeric relationship with the compound (11,), but is represented in this patent in the form of the compound (11).
  • the phenylacetonitrile derivative (3) was treated with alcohol in the presence of hydrochloric acid.
  • the reaction is carried out in an inert solvent such as (DMS 0), tetrahedral flank (THF) or the like to obtain an imidazoline derivative (13).
  • Compound (13) was converted from 5-keto ester derivative (2) with sodium hydride, potassium hydride, sodium methoxide, sodium methoxide, and Yuichi Dimethylformamide (DMF), in the presence or absence of bases such as charium-toxykalyium, potassium carbonate, sodium carbonate, caustic soda, caustic kaly, etc.
  • the condensed pyridone derivative (14) can be synthesized by reacting with or without an inert solvent such as MI), acetonitrile, and toluene.
  • the compound (14) has a tautomeric relationship with the compound (14,), but is represented in this patent in the form of the compound (14).
  • the compound (15) is subsequently converted to a compound of the present invention (1) using a suitable oxidizing agent such as air, NaOCI, DDQ, potassium permanganate or chloranil.
  • a suitable oxidizing agent such as air, NaOCI, DDQ, potassium permanganate or chloranil.
  • synthesis examples of the compound of the present invention and intermediates will be specifically described as examples, but the present invention is not limited thereto.
  • the ether layer was washed with water, a saturated aqueous solution of sodium hydrogencarbonate and water in that order, and dried over anhydrous magnesium sulfate.
  • the ether layer was washed with water, a saturated aqueous solution of sodium carbonate and water in that order, and dried over anhydrous magnesium sulfate.
  • the mixture was extracted with ethyl acetate, and the extract layer was washed with water, dried (anhydrous magnesium sulfate), and the solvent was distilled off under reduced pressure.
  • Black mouth 8 (4-1 Black mouth 2 — Fluoro-5 — methylthiophenyl) 1 5 — Trifluoromethylthimidazo [1,2—a] pyridin 0.4 g, m—Black mouth perbenzoic acid 0.5 g, Black mouth form 30
  • the m1 mixture was stirred at room temperature for 10 hours. The mixture was washed twice with a saturated aqueous solution of sodium hydrogencarbonate and then twice with water, and dried over anhydrous magnesium sulfate.
  • the 50 ml mixture was heated to reflux for 3 hours.
  • the solvent was distilled off under reduced pressure, and the residue was purified with silica gel short column (developing solvent: ether).
  • the solvent was distilled off under reduced pressure to obtain 9.8 g of the desired product as an oil.
  • the solvent was distilled off under reduced pressure, the residue was dissolved in ether, washed with water, and dried (anhydrous magnesium sulfate). The solvent was distilled off under reduced pressure, and the color viscous substance containing the target substance was used for the next reaction as it was.
  • CH CHC0 2 E t, 0 CH 2 C0 2 Me, 0 CH 2 C 0 2 E t, OCH 2 C0 2 P r, OCH2CO2BU, 0 CH 2 C0 2 — tert-Bu, OCH 2 C0 2 Ph, ⁇ CH 2 C0 2 Pn, OCH 2 C0 2 Hex, OCH2CO2-Cyc 1 o-Pn, O CH2CO2-is oPr, 0 CH 2 C0 2 CH 2 Ph, OCH (Me) C0 2 Me, OCH (Me) C0 2 Et, OCH (Me) C0 2 P r, OCH (Me) CO2- is oP r, OCH (Me) C0 2 Pn, OCH (Me) CO2- cyc 1 o -P n, O- (4-But ano li de-2-yl) ⁇ 0- (5-Pentano lide-2-yl), 0— (6-Hexano lide-2
  • NHCO2CH2- (4— F— Ph) ⁇ NHCO2CH2- (4-CF 3 -P h), NHCO2CH2- (2 -F-Ph), NH CO2CH2- (3-F-Ph), NH CO2CH2- (3-C 1 -P h), NHCO2CH2- (2 - CI one Ph), NHCO2CH2- (4 one CF 3 0- Ph) ⁇ NH S OaMe, NH S O2E t , NH SO2P r, NHS0 2 - is o-Pr, NHS0 2 Bu, NHS0 2 CH 2 Ph, NHSO2CHC 1 2> NH S 0 2 CH 2 C 1, NH S0 2 CH 2 CH 2 C 1, NHS 0 2 CH 2 CH 2 CH 2 C 1, NHS0 2 CH 2 CF 3 , NH S O2P h, N

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Abstract

L'invention concerne un nouvel herbicide, ainsi que des composés, et leurs sels, représentés par la formule (I), dans laquelle Rf représente haloalkyle C1-C4; X représente hydrogène, halogéno, etc.; Y représente hydrogène, alkyle C1-C4, etc.; Z1=Z2-Z3 représente N=C(Ra)C(Rb), etc.; Ra et Rb représentent indépendamment hydrogène, alkyle C1-C4, etc.; R1 et R2 représentent indépendamment hydrogène, halogéno, etc.; et R3, R4 et R5 représentent indépendamment hydrogène, halogéno, nitro, cyano, etc.
PCT/JP1999/000451 1998-02-04 1999-02-03 Derives de la pyridine fusionnes avec un azole, et herbicide WO1999040090A1 (fr)

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Application Number Priority Date Filing Date Title
AU22985/99A AU2298599A (en) 1998-02-04 1999-02-03 Pyridine derivatives fused with azole and herbicide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP10/23581 1998-02-04
JP2358198 1998-02-04
JP26633198 1998-09-21
JP10/266331 1998-09-21

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WO1999040090A1 true WO1999040090A1 (fr) 1999-08-12

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002062800A1 (fr) * 2001-02-08 2002-08-15 Eisai Co., Ltd. Composé cyclique fondu azoté bicyclique
JP2008505058A (ja) * 2004-04-13 2008-02-21 セフアロン・インコーポレーテツド チオ−置換ビアリールメタンスルティニル誘導体
WO2011058036A1 (fr) 2009-11-13 2011-05-19 Basf Se Composés tricycliques ayant un effet herbicide
US8431603B2 (en) 2008-04-15 2013-04-30 Eisai R&D Management Co., Ltd. 3-phenylpyrazolo[5,1-b]thiazole compounds
US8530504B2 (en) 2009-10-08 2013-09-10 Eisai R&D Management Co., Ltd. Pyrazolothiazole compound
US20210112813A1 (en) * 2018-10-20 2021-04-22 Nantong Jiangshan Agrochemical & Chemicals Co., Ltd. Herbicidal composition and use thereof

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JPH03181463A (ja) * 1989-11-30 1991-08-07 Schering Ag 除草剤、置換１，２，４―トリアゾロ―〔４，３―ａ〕ピリジンおよび雑草を防除する方法
JPH03251582A (ja) * 1989-02-17 1991-11-11 Takeda Chem Ind Ltd イミダゾ［１，２―ａ］ピリジル化合物
JPH04234881A (ja) * 1990-01-29 1992-08-24 Rhone Poulenc Agrochim トリアゾロピリジン基を有する除草性化合物
WO1996001826A1 (fr) * 1994-07-11 1996-01-25 Dowelanco HERBICIDES AU N-ARYL[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide
JPH09143181A (ja) * 1995-09-22 1997-06-03 Takeda Chem Ind Ltd 新規トリアゾール系化合物、その製造法、中間体および農薬

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JPH03251582A (ja) * 1989-02-17 1991-11-11 Takeda Chem Ind Ltd イミダゾ［１，２―ａ］ピリジル化合物
JPH03181463A (ja) * 1989-11-30 1991-08-07 Schering Ag 除草剤、置換１，２，４―トリアゾロ―〔４，３―ａ〕ピリジンおよび雑草を防除する方法
JPH04234881A (ja) * 1990-01-29 1992-08-24 Rhone Poulenc Agrochim トリアゾロピリジン基を有する除草性化合物
WO1996001826A1 (fr) * 1994-07-11 1996-01-25 Dowelanco HERBICIDES AU N-ARYL[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide
JPH09143181A (ja) * 1995-09-22 1997-06-03 Takeda Chem Ind Ltd 新規トリアゾール系化合物、その製造法、中間体および農薬

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002062800A1 (fr) * 2001-02-08 2002-08-15 Eisai Co., Ltd. Composé cyclique fondu azoté bicyclique
JPWO2002062800A1 (ja) * 2001-02-08 2004-06-10 エーザイ株式会社 二環性含窒素縮合環化合物
US7078405B2 (en) 2001-02-08 2006-07-18 Eisai Co., Ltd. Imidazo[1,2-b]pyridazine compound
US7772249B2 (en) 2001-02-08 2010-08-10 Eisai R&D Management Co., Ltd. Imidazo[1,2-b]pyridazine compound
JP2008505058A (ja) * 2004-04-13 2008-02-21 セフアロン・インコーポレーテツド チオ−置換ビアリールメタンスルティニル誘導体
JP4859828B2 (ja) * 2004-04-13 2012-01-25 セフアロン・インコーポレーテツド チオ−置換ビアリールメタンスルティニル誘導体
US8431603B2 (en) 2008-04-15 2013-04-30 Eisai R&D Management Co., Ltd. 3-phenylpyrazolo[5,1-b]thiazole compounds
US8530504B2 (en) 2009-10-08 2013-09-10 Eisai R&D Management Co., Ltd. Pyrazolothiazole compound
WO2011058036A1 (fr) 2009-11-13 2011-05-19 Basf Se Composés tricycliques ayant un effet herbicide
US20210112813A1 (en) * 2018-10-20 2021-04-22 Nantong Jiangshan Agrochemical & Chemicals Co., Ltd. Herbicidal composition and use thereof
US11758908B2 (en) * 2018-10-20 2023-09-19 Nantong Jiangshan Agrochemical & Chemicals Co., Ltd. Herbicidal composition and use thereof

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