EP0920415A1 - Phenylepyridine substituee en 2 comme herbicide - Google Patents

Phenylepyridine substituee en 2 comme herbicide

Info

Publication number
EP0920415A1
EP0920415A1 EP97938899A EP97938899A EP0920415A1 EP 0920415 A1 EP0920415 A1 EP 0920415A1 EP 97938899 A EP97938899 A EP 97938899A EP 97938899 A EP97938899 A EP 97938899A EP 0920415 A1 EP0920415 A1 EP 0920415A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
formula
hydrogen
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP97938899A
Other languages
German (de)
English (en)
Inventor
Peter Schäfer
Michael Rack
Gerhard Hamprecht
Helmut Walter
Karl-Otto Westphalen
Ulf Misslitz
Markus Menges
Cyrill Zagar
Olaf Menke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0920415A1 publication Critical patent/EP0920415A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings

Definitions

  • the present invention relates to new substituted 2-phenylpyridines of the formula I.
  • R 1 ercapto, hydroxysulfonyl, chlorosulfonyl, aminosulfonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfonyl,
  • R 4 cyano, hydroxy, halogen, -CC 6 alkoxy or phenylmethoxy, where the phenyl ring can be unsubstituted or can carry one to three substituents, each selected from the group consisting of hydroxy, halogen, Ci-Cg-alkyl, C ⁇ -C 6 -haloalkyl, -C-C6-alkoxy, Ci-C ⁇ -haloalkoxy, hydroxycarbonyl, (C ⁇ -C 6 -alkoxy) carbonyl and (C ⁇ -C 6 -alkoxy) - carbonyl -C ⁇ -C 6 - alkoxy;
  • R 8 is hydrogen, hydroxy, C ⁇ -C6 alkyl, hydroxycarbonyl -C -C ⁇ - alkyl, (Ci -C 6 -alkoxy) carbonyl -C -C 6 - alkyl, Ci-C6 - alkoxy, C ⁇ -C 6 - Halogenalkoxy, phenyl -C-C 6 alkoxy, C 3 -Cg -alkenyloxy or C 3 -C 6 -alkynyloxy or
  • R 9 are hydrogen, C 6 alkyl, Ci -C 6 haloalkyl, C 3 -C 6 alkenyl, - C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl or C ⁇ -C 6 alkoxy C ⁇ -C 6 alkyl;
  • R 1X -R 14 independently of one another are hydrogen, Ci-Cg-alkyl or (Ci-C ⁇ -alkoxy) carbonyl;
  • the invention also relates to the use of the compounds I as herbicides or for
  • Cx-C ⁇ alkoxy for: e.g. OCH 3 , OC 2 H 5 , n-propoxy, OCH (CH 3 ) 2 , n-butoxy, 0CH (CH 3 ) -C 2 H 5 , OCH 2 -CH (CH 3 ) 2 , OC (CH 3 ) 3 , n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethyl- propoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy,
  • (C ⁇ -C 6 -alkoxy) carbonyl-Ci-C ⁇ -alkyl for: C (-Ce-alkyl substituted by (C ⁇ -C 6 ⁇ alkoxy) carbonyl as mentioned above, e.g. for CH 2 COOCH 3 , CH 2 COOC 2 H 5 , CH 2 COOCH 2 -C 2 H 5 , CH 2 COOCH (CH 3 ) 2 , CH 2 COOCH 2 CH 2 -C 2 H 5 , (1-methylpropoxycarbonyl) methyl, (2-methylpropoxycarbonyl) methyl, CH 2 COOC (CH 3 ) 3 , CH 2 COO (CH 2 ) 3 -C 2 H 5 , CH 2 COO (CH 2 ) 4 -C 2 H 5 , CH (CH 3 ) COOCH 3 , CH (CH 3 ) COOC 2 H 5 , CH 2 CH 2 COOCH 3 , CH 2 CH 2 COOCH 3 , CH 2 CH 2 COOC 2 H 5 , CH 2
  • C ⁇ -C 6 alkylthio for: for example SCH 3 , SC 2 H 5 , n-propylthio, SCH (CH 3 ) 2 , n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC (CH 3 ) 3 , n-pentylthio , 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio -Methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2,3-d
  • C 3 -C 6 alkenyloxy for: for example prop-1-en-l-yloxy, allyloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy, 1-methylprop-l-en-l-yloxy, 2-methylprop-l-en-1-yloxy, l-methylprop-2-en-l-yloxy, 2-methylprop-2-en- 1-yloxy, n- Penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yl - oxy, n-penten-4-yloxy, 1-methylbut-l-en-l-yloxy, 2-methyl-but- 1-en-l-yloxy, 3-methylbut-l-en-l-yloxy, l-methylbut-2-en-1-yloxy, 2-methylbut-2-en-l-yloxy, 3-methylbut-2- en-l-y
  • R 5 is hydrogen, nitro, cyano, hydroxylamino, C ⁇ -C 6 alkyl
  • R 6 is hydrogen, C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or -C-C 6 alkoxy-C -C 6 alkyl;
  • R 15 C ⁇ -C 6 alkyl
  • Suitable solvents are e.g. Water, sulfuric acid, carboxylic acids such as acetic acid and trifluoroacetic acid and halogenated hydrocarbons such as dichloromethane and chloroform.
  • the oxidizing agent is normally used in at least equimolar amounts, based on the starting compound. In general, an excess of oxidizing agent has proven to be particularly advantageous.
  • the substituted 2-phenylpyridines I can normally be prepared by one of the synthesis processes mentioned above. For economic or procedural reasons, however, it may be more expedient to prepare some compounds I from similar 2-phenylpyridines, but which differ in the meaning of a radical.
  • the diazotization can also take place in the presence of disulfide VII.
  • mineral oil fractions of medium to high boiling point such as
  • Kerosene and diesel oil also coal tarols and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • Paraffins etrahydronaphthalene
  • alkylated naphthalenes and their derivatives alkylated benzenes and their derivatives
  • alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol
  • ketones such as cyclohexanone
  • strongly polar solvents e.g.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium s
  • the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not struck wherever possible, while the active ingredients on the leaves underneath are growing undesirably Plants or the uncovered floor area (post-directed, lay-by).
  • the substituted 2-phenylpyridines I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • 1,2,4-thiazadiols, 1,3,4-thiadiazoles, amide, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy- / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and their derivatives, benzo come as mixing partners - thiadiazinone, 2 - (hetaroyl / aroyl) - 1, 3 -cyclohexanedione, heteroaryl-aryl-ke one, benzylisoxazolidinones, meta-CF-phenyl derivatives, carbamates, quinoline carboxylic acid and their derivatives, chloroacetanilides, cyclohexane-1, 3 -dione derivatives, diazines, dichlor

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne la phénylpyridine substituée en 2 et ses sels (I), où R1 = SH, SO¿2?OH, SO2C1, SO2NH2, C1-C6-alkylthio, C1-C6-alkyl-sulfinyle, C1-C6-alkylsulfonyle, C1-C6-alkylaminosulfonyle, Di-(C1-C6-alkyl)aminosulfonyle; R?2, R3¿ = H, halogène; R4 = CN, OH, halogène, C¿1?-C6-alkoxy, OCH2-phényle éventuellement substitué; et ont les significations indiquées dans la revendication 1. En outre, l'invention concerne: l'utilisation des composés (I) comme herbicides ou comme agents de dessiccation/défoliation des plantes, les herbicides et les agents de dessiccation et/ou défoliation contenant les composés (I) comme substances actives, les procédés de lutte contre les plantes parasites et de dessiccation/défoliation de plantes par les composés (I), les procédés de production des composés (I), d'agents herbicides et d'agents de dessiccation et/ou défoliation de plantes par les composés (I), ainsi que les composés intermédiaires correspondant aux formules (IIa, V et VI).
EP97938899A 1996-08-22 1997-08-13 Phenylepyridine substituee en 2 comme herbicide Withdrawn EP0920415A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19633746 1996-08-22
DE19633746A DE19633746A1 (de) 1996-08-22 1996-08-22 Substituierte 2-Phenylpyridine
PCT/EP1997/004420 WO1998007700A1 (fr) 1996-08-22 1997-08-13 Phenylepyridine substituee en 2 comme herbicide

Publications (1)

Publication Number Publication Date
EP0920415A1 true EP0920415A1 (fr) 1999-06-09

Family

ID=7803264

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97938899A Withdrawn EP0920415A1 (fr) 1996-08-22 1997-08-13 Phenylepyridine substituee en 2 comme herbicide

Country Status (8)

Country Link
US (1) US6448205B1 (fr)
EP (1) EP0920415A1 (fr)
JP (1) JP2000517303A (fr)
AR (1) AR009305A1 (fr)
AU (1) AU4118397A (fr)
CA (1) CA2263093A1 (fr)
DE (1) DE19633746A1 (fr)
WO (1) WO1998007700A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59808196D1 (de) 1997-09-17 2003-06-05 Basf Ag Substituierte 2-phenyl-3(2h)-pyridazinone
WO2000042015A1 (fr) 1999-01-15 2000-07-20 Basf Aktiengesellschaft 2-phenylpyridines substituees utilisees comme herbicides
US20040043903A1 (en) * 2000-11-22 2004-03-04 Michael Puhl 2-Aryl-5-trifluoromethylpyridines
WO2004009551A1 (fr) * 2002-07-23 2004-01-29 Kuraray Co., Ltd. Procede de production d'un derive de pyridine 2-substitue
JP4208512B2 (ja) 2002-07-23 2009-01-14 株式会社クラレ ５−（２’−ピリジル）−２−ピリドン誘導体の製造方法
CN105712926B (zh) * 2014-12-05 2019-01-04 沈阳中化农药化工研发有限公司 取代的联芳香基苯磺酰胺类化合物及其用途
MX2017007874A (es) * 2014-12-24 2018-01-24 Lg Chemical Ltd Derivado de biarilo como agonista de gpr120.

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2229611C3 (de) 1972-06-19 1980-07-17 Boehringer Mannheim Gmbh, 6800 Mannheim Diagnostischer Nachweis von Urobilinogen-Körpern
US4405552A (en) * 1981-03-03 1983-09-20 Eli Lilly And Company 1-Benzoyl-3-(arylphyridyl)urea compounds
GB8333830D0 (en) * 1983-12-20 1984-02-01 Kodak Ltd Photographic dye image compounds
JPH08501100A (ja) 1992-09-09 1996-02-06 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー 除草性ベンゼン化合物
GB9222253D0 (en) 1992-10-23 1992-12-09 Celltech Ltd Chemical compounds
DE4323916A1 (de) * 1993-07-16 1995-01-19 Basf Ag Substituierte 2-Phenylpyridine
DE19500760A1 (de) * 1995-01-13 1996-07-18 Basf Ag Substituierte 2-Phenylpyridine
DE19500911A1 (de) 1995-01-13 1996-07-18 Basf Ag Substituierte 2-Phenylpyridine
DE19500758A1 (de) 1995-01-13 1996-07-18 Basf Ag Substituierte 2-Phenylpyridine
DE19528943A1 (de) 1995-08-07 1997-02-13 Basf Ag Substituierte 2-Phenylpyridine
DE19534466A1 (de) 1995-09-18 1997-03-20 Basf Ag Substituierte 2-Phenylpyridine
DE19605766A1 (de) 1996-02-16 1997-08-21 Basf Ag Substituierte 2-Phenylpyridine
DE19610571A1 (de) 1996-03-18 1997-09-25 Basf Ag Verfahren und Zwischenprodukte zur Herstellung von Pyridyl-4-Fluoranilinen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9807700A1 *

Also Published As

Publication number Publication date
AU4118397A (en) 1998-03-06
AR009305A1 (es) 2000-04-12
DE19633746A1 (de) 1998-02-26
US6448205B1 (en) 2002-09-10
WO1998007700A1 (fr) 1998-02-26
JP2000517303A (ja) 2000-12-26
CA2263093A1 (fr) 1998-02-26

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