WO1999052878A1 - Pyridazinones de phenyle substituees - Google Patents

Pyridazinones de phenyle substituees Download PDF

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Publication number
WO1999052878A1
WO1999052878A1 PCT/EP1999/002086 EP9902086W WO9952878A1 WO 1999052878 A1 WO1999052878 A1 WO 1999052878A1 EP 9902086 W EP9902086 W EP 9902086W WO 9952878 A1 WO9952878 A1 WO 9952878A1
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WIPO (PCT)
Prior art keywords
fluorine
chlorine
cyano
alkyl
diyl
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PCT/EP1999/002086
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German (de)
English (en)
Inventor
Karl-Heinz Linker
Achim Hupperts
Mark Wilhelm Drewes
Markus Dollinger
Ingo Wetcholowsky
Christoph Erdelen
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Bayer Aktiengesellschaft
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Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to BR9909548-3A priority Critical patent/BR9909548A/pt
Priority to CA002327806A priority patent/CA2327806A1/fr
Priority to AU37025/99A priority patent/AU742108B2/en
Priority to EP99919146A priority patent/EP1070055A1/fr
Priority to KR1020007010988A priority patent/KR20010042411A/ko
Priority to JP2000543440A priority patent/JP2002511452A/ja
Publication of WO1999052878A1 publication Critical patent/WO1999052878A1/fr

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    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C255/65—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms
    • C07C255/66—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms having cyano groups and nitrogen atoms being part of hydrazine or hydrazone groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D237/14—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • 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

Definitions

  • the invention relates to new substituted phenylpyridazinones, processes for their preparation and their use as plant treatment agents, in particular as herbicides and as insecticides.
  • R.1 represents hydrogen, fluorine, chlorine or bromine
  • R2 represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or alkyl, alkoxy or alkylthio, each optionally substituted by fluorine and / or chlorine, each having 1 or 2 carbon atoms,
  • R.3 stands for the grouping -A ⁇ -A ⁇ -A ⁇ , - 2 -
  • Al stands for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁇ -, wherein A ⁇ stands for hydrogen, hydroxy, -C -C 4 alkyl, C3-C-alkenyl , C 3 -C alkynyl, C! -C 4 -
  • A2 stands for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁇ -, where A ⁇ stands for hydrogen, hydroxy, Ci ⁇ C ⁇ alkyl, -C -C4 alkoxy, Phenyl, C 1 -C 4 -alkylsulfonyl or phenylsulfonyl,
  • R5 for hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or for alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl, each optionally substituted by fluorine and / or chlorine 1 to 4 carbon atoms in the alkyl groups, and
  • R6 for hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro,
  • the new substituted phenylpyridazinones of the general formula (I) have interesting biological properties; they are particularly notable for their strong herbicidal and insecticidal activity.
  • saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl, are each straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Rl preferably represents hydrogen, fluorine or chlorine
  • R2 preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl;
  • R ⁇ preferably represents the grouping -A ⁇ -A ⁇ -A ⁇ , in which
  • Al stands for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁇ -, where A ⁇ stands for hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,
  • A2 stands for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the group -NA ⁇ -, where A ⁇ stands for hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
  • R4 preferably represents hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl;
  • R5 preferably represents hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio,
  • R ⁇ preferably represents hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or methyl, ethyl, n- or i, each optionally substituted by fluorine and / or chlorine -Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl.
  • R * particularly preferably represents hydrogen, fluorine or chlorine
  • R2 particularly preferably represents cyano or thiocarbamoyl
  • R3 particularly preferably represents the grouping -A ⁇ -A ⁇ -A ⁇ , - 8th -
  • A stands for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁇ -, wherein A ⁇ stands for hydrogen, methyl, ethyl, n- or i-propyl, methylsulfonyl or ethylsulfonyl stands,
  • a ⁇ represents a single bond, represents oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁇ -, where A ⁇ represents hydrogen, methyl, ethyl, n- or i-propyl, methoxy, Ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
  • A- ⁇ furthermore for pyrazolyl, imidazolyl, triazolyl, furyl, thienyl,
  • R5 particularly preferably represents methyl, ethyl, n- or i-propyl substituted by fluorine and / or chlorine;
  • R6 particularly preferably stands for hydrogen, cyano, thiocarbamoyl, nitro, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino which is optionally substituted by fluorine and / or chlorine , Ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1. - 15 -
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1. - 16 -
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1. 19
  • N ⁇ * Ar— N> - CHF
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1. - 22 -
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • R, R2 and R ⁇ have the meaning given above and
  • X 1 represents halogen
  • R ⁇ , R5 and R6 have the meaning given above,
  • R, R ⁇ and R ⁇ have the meaning given above,
  • ⁇ 2 represents halogen
  • R, R ⁇ , R3, R4 ; R5 and R6 have the meanings given 0 b en
  • R, R ⁇ , R4, R5 and R ⁇ have the meaning given above,
  • R, R ⁇ , R3, R5 and R6 have the meaning given above,
  • R ⁇ has the meaning given above and - 26 -
  • R represents alkyl having 1 to 6 carbon atoms
  • R ⁇ has the meaning given above and
  • R represents alkyl having 1 to 6 carbon atoms
  • Methods can be converted into other compounds of the general formula (I) as defined above, for example by nucleophilic substitution (for example R3 F ⁇ OH, SH, NH2, OCH3, NHS0 2 CH 3 ) or by further conversions of functional groups (for example R 2 : F / Cl / Br ⁇ CN, CONH 2 - CN, CN ⁇ CSNH 2 , N0 2 ⁇ NH 2 ; R 3 : N0 2 ⁇ NH 2 , NH 2 ⁇ F, Cl, Br, CN, NHS0 2 CH 3 , S0 2 C1,
  • nucleophilic substitution for example R3 F ⁇ OH, SH, NH2, OCH3, NHS0 2 CH 3
  • functional groups for example R 2 : F / Cl / Br ⁇ CN, CONH 2 - CN, CN ⁇ CSNH 2 , N0 2 ⁇ NH 2 ; R 3 : N0 2 ⁇ NH 2 , NH 2 ⁇ F, Cl, Br,
  • Formula (I) halogen arenes to be used as starting materials are generally defined by the formula (II).
  • R, R 2 and R 3 preferably or in particular have the meaning which, as described above in the description of the compounds of the formula (I) to be prepared according to the invention, are preferred or as particularly preferred for R, R 2 and R 3 was specified;
  • ⁇ l is preferably fluorine, chlorine or bromine, especially fluorine.
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. EP 191181, EP 370332, EP 431373, EP 441004).
  • Formula (III) provides a general definition of the pyridazinones to be used further as starting materials in process (a) according to the invention.
  • R4, R5 and R ⁇ preferably have the meaning which has already been given above in the description of the compounds of the formula (I) to be prepared according to the invention as being preferred, particularly preferred or very particularly preferred for R% R5 and R ° .
  • the starting materials of the formula (III) are known and / or can be prepared by processes known per se (cf. J. Chem. Soc. 1947, 239; Angew. Chem. 77 (1965), 282; monthly chem. 120 ( 1989), 329).
  • Formula (IV) provides a general definition of the arylhydrazines to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the formula (I).
  • R, R 2 and R 3 preferably have the meaning which are preferred, particularly preferred or very particularly preferred for R, R 2 and already in the description of the compounds of the formula (I) to be prepared according to the invention R 3 was specified.
  • the starting materials of the formula (IV) are known and / or can be prepared by processes known per se (cf. EP 370332).
  • Formula (V) provides a general definition of the ⁇ -trihalomethyl-enones to be used further as starting materials in process (b) according to the invention.
  • Rr, R5 and R preferably have the meaning which has been mentioned above as preferred, particularly preferred or very particularly preferred for R ⁇ in the description of the compounds of the formula (I) to be prepared according to the invention.
  • R ⁇ and R ⁇ was specified;
  • X 2 preferably represents fluorine, chlorine or bromine, especially chlorine.
  • the starting materials of the formula (V) are known and / or can be prepared by processes which are known per se (cf. DE 2706700).
  • Formula (VI) provides a general definition of the hydrazone carboxylic acids to be used as starting materials in process (c) according to the invention for the preparation of the compounds of the formula (I).
  • R, R 2 , R 3 , R4, R5 and R6 preferably have the meaning which has already been mentioned above as preferred, particularly preferred or very particularly preferred for R in the description of the compounds of the formula (I) to be prepared according to the invention , R 2 , R 3 , R4, R and R6 was specified.
  • the starting materials of the formula (VI) are known and / or can be prepared by processes known per se (cf. WO 9639392).
  • R, R 2 and R 3 have the meaning given above
  • R4, R5 and R ⁇ have the meaning given above,
  • a diluent e.g. Ethanol
  • a reaction auxiliary e.g. p-toluenesulfonic acid
  • Formula (I) to be used as starting materials 2,4-disubstituted phenylpyridazinones are generally defined by the formula (Ia).
  • R3 R 2 , R ⁇ , R5 and R ⁇ preferably have the meaning which has already been mentioned above as preferred, particularly preferred or very particularly preferred for R, R in the description of the compounds of the formula (I) to be prepared according to the invention 2 , R ⁇ , R5 and R6 was specified.
  • the starting materials of the formula (Ia) are known and / or can be prepared by processes known per se (cf. processes (a) to (c) according to the invention).
  • Formula (VII) provides a general definition of the hydrazone carbonyl compounds to be used as starting materials in process (e) according to the invention for the preparation of compounds of the formula (I).
  • R, R 2 , R 3 , R-> and R preferably or in particular have those meanings which are preferred, particularly preferred or entirely in connection with the description of the compounds of the formula (I) according to the invention were particularly preferably indicated for R, R 2 , R 3 , R5 and R ". 32
  • the starting materials of the formula (VII) are known and / or can be prepared by processes known per se (cf. WO 9707104).
  • R represents fluorine, chlorine or bromine
  • R 2 represents cyano, carbamoyl, thiocarbamoyl, or alkyl, alkoxy or alkylthio, each optionally substituted by fluorine and / or chlorine, each having 1 or 2 carbon atoms,
  • R 3 represents the grouping -Al-A 2 -A 3 ,
  • AI stands for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁇ -, wherein A ⁇ stands for hydrogen, hydroxy, C 1 -C 4 alkyl, C3-C4 alkenyl , C 3 -C 4 alkynyl, C1-C4 alkoxy, phenyl, -C ⁇ -C4 alkylsulfonyl or phenylsulfonyl, - 33 -
  • a 2 stands for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the group -NA ⁇ -, wherein A ⁇ stands for hydrogen, hydroxy, C ⁇ alkyl, -C-C4-Alko y , Phenyl, C 1 -C 4 alkylsulfonyl or phenylsulfonyl,
  • a 2 furthermore for C, -C6-alkanediyl, C2-Cg-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkynediyl, C3-Cg-cycloalkanediyl, C3-Cg-cycloalkanediyl, C3-C5-, in each case optionally substituted by fluorine, chlorine or bromine Cycloalkenediyl or phenylene,
  • Alkenyl, alkylidene or alkynyl groups each for cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxy, optionally substituted by fluorine, chlorine, cyano, carboxy, C1-C4-alkyl and / or C-C4-alkoxy-carbonyl carbonyl or cycloalkylalkoxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 - 34 -
  • a 3 furthermore for each optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
  • R5 for hydrogen, cyano, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms in the Stands for alkyl groups, and
  • R6 for hydrogen, cyano, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms in the Alkyl groups.
  • R5 and R ⁇ have the meaning given above and
  • X 3 represents halogen (especially chlorine or bromine),
  • a diluent e.g. Water
  • a reaction auxiliary such as e.g. Sodium acetate
  • R represents alkyl (preferably methyl or ethyl)
  • R, R, R 2 ", R 3 and R ⁇ have the meaning given above,
  • the formulas (VIII) and (IX) generally define the alkoxycarbonylmethylene-phosphoranes or phosphonocarboxylic acid trialkyl esters to be used as starting materials in process (e) according to the invention for the preparation of compounds of the formula (I).
  • R preferably has the meaning which has already been given above as preferred, particularly preferred or very particularly preferred for R4 in connection with the description of the compounds of the formula (I) according to the invention; R each preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.
  • the starting materials of the formulas (VIII) and (IX) are known synthetic chemicals.
  • aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane (chloroform or carbon tetrachloride, dialkyl ethers, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether, ethyl t-butyl ether, methyl t-pentyl ether (MTBE), ethyl t-pentyl ether, tetrahydrofuran (THF), 1,4-dioxane , Ethylene glycol dimethyl
  • acetic acid can also advantageously be used as the diluent.
  • Processes (a), (b) and (e) according to the invention for the preparation of the compounds of the formula (I) are preferably carried out in the presence of a suitable reaction auxiliary.
  • a suitable reaction auxiliary The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates,
  • bicarbonates, hydrides, hydroxides or alkanolates such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, Potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, - ethanolate, n- or i-propanolate , n-, i-, s- or t-butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-di- methyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4
  • DABCO 1,4-diazabicyclo [2, 2,2] octane
  • DBN 1,5-diazabicyclo [4,3,0] non-5-ene
  • DBU 1,8-diazabicyclo [5,4,0] undec-7- en
  • Process (c) according to the invention for the preparation of the compounds of the formula (I) is carried out in the presence of a dehydrating agent.
  • a dehydrating agent such as sulfuric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, acetic anhydride and phosphorus (V) oxide.
  • Process (d) according to the invention for the preparation of the compounds of the formula (I) is carried out using a nitrating agent.
  • a nitrating agent e.g. Nitric acid and mixtures thereof with nitration aids, e.g. Sulfuric acid.
  • reaction temperatures can be varied within a substantial range when carrying out processes (a), (b), (c), (d) and (e). In general, temperatures between -20 ° C and + 200 ° C, preferably between 0 ° C and 150 ° C, in particular between 10 ° C and 120 ° C.
  • the processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent, if appropriate in the presence of a reaction auxiliary, and that
  • the reaction mixture is generally stirred for several hours at the required temperature.
  • Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in the following plants: - 40 -
  • Brassica, lactuca, cucumis, cucurbita Brassica, lactuca, cucumis, cucurbita.
  • Scirpus Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops for example forest, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop- - 41 -
  • plants on ornamental and sports turf and pastures and for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
  • Oils Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
  • Possible solid carriers are: e.g. Ammonium salts and natural
  • Rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont- - 42 -
  • Morillonite or diatomaceous earth and synthetic rock powder such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,
  • coconut shells, corn cobs and tobacco stems as emulsifying and or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite waste liquor and
  • Methyl cellulose Methyl cellulose.
  • Carboxymefhylcellulose natural and synthetic powdered, granular or latexf '-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids in the formulations adhesives.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example - 43 -
  • Imazapyr Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron, Ioxynil, Iso-propalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MetCPam, Methonazon, Methobenz Metobromuron, (alpha-) metolchloro, metosulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orben- - 44 -
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha. - 45 -
  • Example 15 the compound listed above in Table 1 as Example 15 can be made as follows:
  • Example 18 The compound listed as Example 18 in Table 1 above can be prepared, for example, as follows:
  • Example 122 the compound listed above in Table 1 as Example 122 can be made as follows:
  • Example 129 the compound listed above in Table 1 as Example 129 can be made as follows:
  • the compound listed as Table 107 above in Table 1 can be produced, for example, as follows: - 71

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

Abstract

L'invention concerne de nouvelles pyridazinones de phényle substituées de la formule (I) dans laquelle R?1, R2, R3, R4, R5 et R6¿ ont la signification mentionnée dans la description. L'invention concerne en outre des procédés permettant de les préparer, leur utilisation comme herbicides, ainsi que de nouveaux produits intermédiaires.
PCT/EP1999/002086 1998-04-09 1999-03-26 Pyridazinones de phenyle substituees WO1999052878A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BR9909548-3A BR9909548A (pt) 1998-04-09 1999-03-26 Fenilpiridazinonas substituìdas
CA002327806A CA2327806A1 (fr) 1998-04-09 1999-03-26 Pyridazinones de phenyle substituees
AU37025/99A AU742108B2 (en) 1998-04-09 1999-03-26 Substituted phenyl pyridazinones
EP99919146A EP1070055A1 (fr) 1998-04-09 1999-03-26 Pyridazinones de phenyle substituees
KR1020007010988A KR20010042411A (ko) 1998-04-09 1999-03-26 치환된 페닐 피리다지논
JP2000543440A JP2002511452A (ja) 1998-04-09 1999-03-26 置換フェニルピリダジノン類

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19815947.1 1998-04-09
DE19815947 1998-04-09
DE19859685.5 1998-12-23
DE19859685 1998-12-23

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WO1999052878A1 true WO1999052878A1 (fr) 1999-10-21

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EP (1) EP1070055A1 (fr)
JP (1) JP2002511452A (fr)
KR (1) KR20010042411A (fr)
CN (1) CN1305466A (fr)
AU (1) AU742108B2 (fr)
BR (1) BR9909548A (fr)
CA (1) CA2327806A1 (fr)
WO (1) WO1999052878A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000034249A1 (fr) * 1998-12-09 2000-06-15 Sumitomo Chemical Company, Limited Procede de preparation de derives de pyridazin-3-on
US6303543B1 (en) 1998-09-11 2001-10-16 Ishihara Sangyo Kaisha, Ltd. Diaryl ethers and processes for their preparation and herbicidal and desiccant compositions containing them
WO2001079183A1 (fr) * 2000-04-14 2001-10-25 Basf Aktiengesellschaft 2-phenyl-2h-pyridazin-3-ones
WO2001079182A1 (fr) * 2000-04-14 2001-10-25 Basf Aktiengesellschaft 2-phenyle-2h-pyridazine-3-one
WO2002006244A1 (fr) * 2000-07-18 2002-01-24 Bayer Aktiengesellschaft Anilide de l'acide sulfonique herbicide heterocycliquement substitue
CN101041639B (zh) * 2005-03-17 2010-05-26 南开大学 4-取代苯基哒嗪类化合物及除草活性
US8969347B2 (en) 2008-06-03 2015-03-03 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US9359379B2 (en) 2012-10-02 2016-06-07 Intermune, Inc. Anti-fibrotic pyridinones
US9434695B2 (en) 2012-07-18 2016-09-06 Sunshine Lake Pharma Co., Ltd Nitrogenous heterocyclic derivatives and their application in drugs
US9527816B2 (en) 2005-05-10 2016-12-27 Intermune, Inc. Method of modulating stress-activated protein kinase system
US10233195B2 (en) 2014-04-02 2019-03-19 Intermune, Inc. Anti-fibrotic pyridinones
US20190124926A1 (en) * 2016-04-15 2019-05-02 Syngenta Participations Ag Herbicidal pyridazinone compounds
US11254643B2 (en) 2017-10-18 2022-02-22 Syngenta Participations Ag Process for producing herbicidal pyridazinone compounds

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Publication number Priority date Publication date Assignee Title
US7741485B2 (en) 2003-04-08 2010-06-22 Basf Aktiengesellschaft Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds
JP5842594B2 (ja) * 2010-12-27 2016-01-13 住友化学株式会社 ピリダジノン化合物、それを含有する除草剤及び有害節足動物防除剤
GB201121317D0 (en) * 2011-12-09 2012-01-25 Syngenta Ltd Herbicidal compounds
CN103664795B (zh) * 2012-09-06 2017-10-03 华东理工大学 哒嗪酮类化合物及其用途

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WO1998017632A1 (fr) * 1996-10-21 1998-04-30 Sumitomo Chemical Company, Limited Production d'herbicides a la pyridazine
WO1998017633A1 (fr) * 1996-10-21 1998-04-30 Sumitomo Chemical Company, Limited Production d'herbicides a la pyridazine
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EP0860435A1 (fr) * 1997-02-19 1998-08-26 Sumitomo Chemical Company, Limited Dérivés de pyridazin-3-one et leur utilisation
EP0860434A1 (fr) * 1997-02-20 1998-08-26 Sumitomo Chemical Company, Limited Dérivés de pyridazin-3-one et leur utilisation

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CH373919A (de) * 1959-02-02 1963-12-15 Ciba Geigy Verfahren zum Bekämpfen von Unkräutern
EP0003805A1 (fr) * 1978-02-25 1979-09-05 BASF Aktiengesellschaft Pyridazones et compositions herbicides les contenant
DE2808193A1 (de) * 1978-02-25 1979-09-06 Basf Ag Pyridazon-verbindungen
WO1996039392A1 (fr) * 1995-06-06 1996-12-12 Bayer Aktiengesellschaft Phenylpyridazinones
DE19520613A1 (de) * 1995-06-06 1996-12-12 Bayer Ag Phenylpyridazinone
WO1997007104A1 (fr) * 1995-08-21 1997-02-27 Sumitomo Chemical Company, Limited Derives de pyridazin-3-one, leur utilisation et intermediaires destines a leur production
WO1998017632A1 (fr) * 1996-10-21 1998-04-30 Sumitomo Chemical Company, Limited Production d'herbicides a la pyridazine
WO1998017633A1 (fr) * 1996-10-21 1998-04-30 Sumitomo Chemical Company, Limited Production d'herbicides a la pyridazine
DE19754348A1 (de) * 1996-12-11 1998-06-18 Ciba Geigy Ag Neue Herbizide
EP0860435A1 (fr) * 1997-02-19 1998-08-26 Sumitomo Chemical Company, Limited Dérivés de pyridazin-3-one et leur utilisation
EP0860434A1 (fr) * 1997-02-20 1998-08-26 Sumitomo Chemical Company, Limited Dérivés de pyridazin-3-one et leur utilisation

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6303543B1 (en) 1998-09-11 2001-10-16 Ishihara Sangyo Kaisha, Ltd. Diaryl ethers and processes for their preparation and herbicidal and desiccant compositions containing them
US6500951B1 (en) 1998-12-09 2002-12-31 Sumitomo Chemical Company, Limited Process for preparing pyridazin-3-on derivatives
WO2000034249A1 (fr) * 1998-12-09 2000-06-15 Sumitomo Chemical Company, Limited Procede de preparation de derives de pyridazin-3-on
WO2001079183A1 (fr) * 2000-04-14 2001-10-25 Basf Aktiengesellschaft 2-phenyl-2h-pyridazin-3-ones
WO2001079182A1 (fr) * 2000-04-14 2001-10-25 Basf Aktiengesellschaft 2-phenyle-2h-pyridazine-3-one
WO2002006244A1 (fr) * 2000-07-18 2002-01-24 Bayer Aktiengesellschaft Anilide de l'acide sulfonique herbicide heterocycliquement substitue
CN101041639B (zh) * 2005-03-17 2010-05-26 南开大学 4-取代苯基哒嗪类化合物及除草活性
US10010536B2 (en) 2005-05-10 2018-07-03 Intermune, Inc. Method of modulating stress-activated protein kinase system
US9527816B2 (en) 2005-05-10 2016-12-27 Intermune, Inc. Method of modulating stress-activated protein kinase system
US8969347B2 (en) 2008-06-03 2015-03-03 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US9290450B2 (en) 2008-06-03 2016-03-22 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
USRE47142E1 (en) 2008-06-03 2018-11-27 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US9434695B2 (en) 2012-07-18 2016-09-06 Sunshine Lake Pharma Co., Ltd Nitrogenous heterocyclic derivatives and their application in drugs
US9675593B2 (en) 2012-10-02 2017-06-13 Intermune, Inc. Anti-fibrotic pyridinones
US9359379B2 (en) 2012-10-02 2016-06-07 Intermune, Inc. Anti-fibrotic pyridinones
US10376497B2 (en) 2012-10-02 2019-08-13 Intermune, Inc. Anti-fibrotic pyridinones
US10898474B2 (en) 2012-10-02 2021-01-26 Intermune, Inc. Anti-fibrotic pyridinones
US10233195B2 (en) 2014-04-02 2019-03-19 Intermune, Inc. Anti-fibrotic pyridinones
US10544161B2 (en) 2014-04-02 2020-01-28 Intermune, Inc. Anti-fibrotic pyridinones
US20190124926A1 (en) * 2016-04-15 2019-05-02 Syngenta Participations Ag Herbicidal pyridazinone compounds
US10813354B2 (en) * 2016-04-15 2020-10-27 Syngenta Participations Ag Herbicidal pyridazinone compounds
US11254643B2 (en) 2017-10-18 2022-02-22 Syngenta Participations Ag Process for producing herbicidal pyridazinone compounds

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JP2002511452A (ja) 2002-04-16
CN1305466A (zh) 2001-07-25
EP1070055A1 (fr) 2001-01-24
AU3702599A (en) 1999-11-01
CA2327806A1 (fr) 1999-10-21
KR20010042411A (ko) 2001-05-25
AU742108B2 (en) 2001-12-20
BR9909548A (pt) 2000-12-12

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