[go: up one dir, main page]

CA2327806A1 - Substituted phenyl pyridazinones - Google Patents

Substituted phenyl pyridazinones Download PDF

Info

Publication number
CA2327806A1
CA2327806A1 CA002327806A CA2327806A CA2327806A1 CA 2327806 A1 CA2327806 A1 CA 2327806A1 CA 002327806 A CA002327806 A CA 002327806A CA 2327806 A CA2327806 A CA 2327806A CA 2327806 A1 CA2327806 A1 CA 2327806A1
Authority
CA
Canada
Prior art keywords
chlorine
alkyl
cyano
fluorine
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.)
Abandoned
Application number
CA002327806A
Other languages
French (fr)
Inventor
Karl-Heinz Linker
Achim Hupperts
Mark Wilhelm Drewes
Markus Dollinger
Ingo Wetcholowsky
Christoph Erdelen
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.)
Bayer AG
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2327806A1 publication Critical patent/CA2327806A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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

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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to novel substituted phenyl pyridazinones of formula (I), wherein R1, R2, R3, R4, R5 and R6 have the meanings cited in the description. The invention also relates to the production and use thereof as herbicides. The invention further relates to novel intermediate products.

Description

''' Le A 32 986-Foreign Countries Kri/wa/NT

Substituted uhenylpyridazinones The invention relates to novel substituted phenylpyridazinones, to processes for their preparation and to their use as crop protection agents, in particular as herbicides and S as insecticides.
It is already known that certain substituted phenylpyridazinones have herbicidal properties (cf. DE-A-1105232, DE-A-1670309, DE-A-1670315, DE-A-1695840, DE-A-2526643, DE-A-2706700, DE-A-2808193, DE-A-2821809, DE-A-19754348, US-A-5298502, WO-A-96/39392, WO-A-97/07104). The herbicidal activity of these compounds is not entirely satisfactory.
This invention, accordingly, provides the novel substituted phenylpyridazinones of the general formula (I) Rs N R' O ~ R2 (I) Rs in which R1 represents hydrogen, fluorine, chlorine or bromine, R2 represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy or alkylthio having in each case 1 or 2 carbon atoms, R3 represents the grouping -A1-A2-A3 Le A 32 986-Foreign Countries in which A1 represents a single bond, represents oxygen, sulphur, -SO-, -S02-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-Cq.-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, A1 furthermore represents in each case optionally fluorine-, chlorine- or bromine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-aza-alkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cyclo-alkenediyl or phenylene, A2 represents a single bond, represents oxygen, sulphur, -SO-, -S02-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, C 1-C4-alkyl, C 1-C4-alkoxy, phenyl, C 1-C4-alkylsulphonyl or phenylsulphonyl, A2 furthermore represents in each case optionally fluorine-, chlorine-, bromine- or C~-C4-alkoxy-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cyclo alkanediyl, C3-C6-cycloalkenediyl or phenylene, A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, formyl, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chloro-sulphonyl, fluorine, chlorine, bromine, represents in each case optionally hydroxyl-, fluorine-, chlorine-, C1-C4-alkoxy-, C~-C4-alkyl-carbonyloxy- or C,-C4-alkoxy-carbonyloxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or di-alkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally fluorine- or chlorine-Le A 32 986-Foreign Countries substituted alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxy-carbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups, represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, C1-C4-alkyl- and/or C1-C4-alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkyl-amino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxy-carbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-halogenoalkyl, C1-C4-alkyloxy, C1-C4-halogenoalkyloxy- and/or C1-C4-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C1-C4-alkyl, phenyl-C1-C4-alkoxy, phenyloxycarbonyl or phenyl-C 1-C4-alkoxycarbonyl, A3 furthermore represents in each case optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, dioxanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1-C4-alkyl, furyl-C1-C4-alkyl, thienyl-C1-C4-alkyl, oxa-zolyl-C1-C4-alkyl, isoxazole-C1-C4-alkyl, thiazole-C1-C4-alkyl, pyridinyl-C1-C4-alkyl, pyrimidinyl-C1-C4-alkyl, pyrazolylmethoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy, R4 represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the alkyl groups, Le A 32 986-Foreign Countries RS represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, vitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the alkyl groups, and R6 represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, vitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the alkyl groups.
The novel substituted phenylpyridazinones of the general formula (I) have interesting biological properties, in particular strong herbicidal and insecticidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
R1 preferably represents hydrogen, fluorine or chlorine;
R2 preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl;
R3 preferably represents the grouping -A1-A2-A3 in which Le A 32 986-Foreim Countries A1 represents a single bond, represents oxygen, sulphur, -SO-, -S02-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl or ethylsulphonyl, S
A1 furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl, A2 represents a single bond, represents oxygen, sulphur, -SO-, -S02-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl or phenylsulphonyl, A2 furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl, A3 represents hydrogen, hydroxyl, amino, cyano, nitro, formyl, carboxyl, carbamoyl, sulpho, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methyl-sulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethyl-amino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-Le A 32 986-Foreign Countries propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl or di-propoxyphosphoryl, diisopropoxyphosphoryl, represents in each case optionally fluorine- or chlorine- substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylidene-amino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxycarbonyl- or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo-propyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclo-propylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl-methyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentyl-methoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclo-hexylideneamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoro-methoxy-, methoxycarbonyl- and/or ethoxycarbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxy-carbonyl, benzyloxycarbonyl, A3 furthermore represents (in each case optionally fully or partially hydrogenated) dioxolanyl, dioxanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-methyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolemethyl, thiazolemethyl, pyridinylmethyl, pyrirnidinylmethyl, pyrazolyl-methoxy, furylmethoxy or pyridylmethoxy;

Le A 32 986-Foreign Countries -R4 preferably represents hydrogen; carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methyl-amino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl;
RS preferably represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methyl-amino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl; and R6 preferably represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methyl-amino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl.
R1 particularly preferably represents hydrogen, fluorine or chlorine;
R2 particularly preferably represents cyano or thiocarbamoyl;
R3 particularly preferably represents the grouping -A1-A2-A3, in which A1 represents a single bond, represents oxygen, sulphur, -SO-, -S02--CO- or the grouping -N-A4-, in which A4 represents hydrogen, methyl, ethyl, n- or i-propyl, methylsulphonyl or ethylsulphonyl, Le A 32 986-Foreign Countries _8_ A1 furthermore represents -methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl or propene-1,3-diyl, A2 represents a single bond, represents oxygen, sulphur, -SO-, -S02-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl or phenyl-sulphonyl, -A2 furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl or propene-1,3-diyl, A3 represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulpho, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methyl-sulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethyl-amino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, represents in each case optionally fluorine- or chlorine-substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propinyl, butinyl, propinyl-oxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxy-Le A 32 986-Foreign Countries carbonyl- or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyl-oxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclo-pentylmethyl, cyclohexylmethyl, cyclo-propylmethoxy, cyclobutyl-methoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidene-amino, cyclohexylidenamino, cyclopentyloxycarbonyl, cyclohexyloxy-carbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxy-carbonyl, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, di-fluoromethoxy-, trifluoromethoxy-, methoxycarbonyl- and/or ethoxy-carbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyl-oxy, phenyloxycarbonyl or benzyloxycarbonyl, A3 furthermore represents pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienyl methyl, oxazolylmethyl, isoxazolemethyl, thiazolemethyl, pyridinyl methyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy;
R4 particularly preferably represents hydrogen, cyano, thiocarbamoyl, nitro, fluorine, chlorine, bromine, or represents in each case optionally fluorine-and/or chlorine- substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino;
R5 particularly preferably represents in each case fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl; and R6 particularly preferably represents hydrogen, cyano, thiocarbamoyl, nitro, fluorine, chlorine, bromine, or represents in each case optionally fluorine-Le A 32 986-Foreign Countries and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxy-carbonyl or ethoxycarbonyl.
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or inter-mediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.
Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Very particularly preferred compounds of the formula (I) are listed in the groups below.
Group 1 F
N-Ar -N / CF3 (~-1 ) O
Ar has here, for example, the meanings listed below:
4-cyano-phenyl, 2-fluoro-4-cyano-phenyl, 2-chloro-4-cyano-phenyl, 3-fluoro-4-cyano-phenyl, 3-chloro-4-cyano-phenyl, 2-fluoro-5-chloro-4-cyano-phenyl, 2,5-dichloro-4-cyano-phenyl, 2-chloro-5-fluoro-4-cyano-phenyl, 2-chloro-4,5-dicyano-phenyl, 2-chloro-4-fluoro-5-cyano-phenyl, 2,5-difluoro-4-cyano-phenyl, 2-chloro-4-Le A 32 986-Forei~~n Countries cyano-5-methyl-phenyl, 2-fluoro-4-cyano-S-methyl-phenyl, 2-chloro-4-cyano-5-tri-fluoromethyl-phenyl, 2-fluoro-4-cyano-5-trifluoromethyl-phenyl, 2,5-difluoro-4-thio-carbamoyl-phenyl, 2-fluoro-4-cyano-5-methoxy-phenyl, 2-fluoro-4-cyano-S-i-pro-poxy-phenyl, 2-chloro-4-cyano-S-(2-propinyloxy)-phenyl, 2-fluoro-4-cyano-5-(1-methyl-2-propinyloxy)-phenyl, 2-chloro-4-thiocarbamoyl-5-i-propoxy-phenyl, 2-fluoro-4-cyano-5-(2-propenyloxy)-phenyl, 2-chloro-4-cyano-5-methylsulphonyl-amino-phenyl, 2-fluoro-4-cyano-5-ethylsulphonylamino-phenyl, 2-fluoro-4-thio-carbamoyl-5-methylsulphonylamino-phenyl, 2-chloro-4-cyano-5-ethylsulphonyl-amino-phenyl, 2-fluoro-4-cyano-5-cyclopropylsulphonylamino-phenyl, 2-fluoro-4-cyano-5-i-propylsulphonylamino-phenyl, 2-chloro-4-thiocarbamoyl-5-ethyl-sulphonylamino-phenyl, 2-chloro-4-cyano-S-cyanamino-phenyl, 2-fluoro-4-cyano-5-trifluoromethylsulphonylamino-phenyl, 2-fluoro-4-cyano-5-(2,2-difluoroethyl-sulphonylamino)-phenyl, 2-fluoro-4-cyano-S-phenylsulphonylamino-phenyl, 2-fluoro-4-cyano-5-t-butylsulphonylamino-phenyl, 2-chloro-4-cyano-S-methoxy-carbonyl-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonyl-phenyl, 2-fluoro-4-thio-carbamoyl-S-methoxycarbonyl-phenyl, 2-fluoro-4-cyano-S-(1-methyl-2-propinyl-thio)-phenyl, 2-fluoro-4-cyano-5-methylamino-phenyl, 2-chloro-4-thiocarbamoyl-methoxycarbonylmethyl-phenyl, 2-chloro-4-cyano-S-(N-methyl-ethylsulphonyl-amino)-phenyl, 2-chloro-4-cyano-5-i-propoxycarbonyl-phenyl, 2-fluoro-4-cyano-5-(bis-ethylsulphonyl-amino)-phenyl, 2-fluoro-4-cyano-5-(N-methylsulphonyl-N-ethyl-sulphonylamino)-phenyl, 2-fluoro-4-cyano-5-( 1-methoxycarbonyl-ethoxy)-phenyl, fluoro-4-cyano-5-cyclopropyloxy-phenyl, 2-chloro-4-cyano-5-dimethylamino-phenyl, 2-fluoro-4-cyano-5-tetrahydrofurylmethoxy-phenyl, 2-fluoro-4-cyano-5-amino-phenyl, 2-fluoro-4-cyano-S-methylaminocarbonyl-phenyl, 2-fluoro-4-cyano-5-methylsulphonyloxy-phenyl, 2-chloro-4-cyano-5-difluoromethoxy-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonylmethoxy-phenyl, 2-fluoro-4-cyano-S-dimethylamino-carbonyl-phenyl, 2-fluoro-4-cyano-5-cyanomethoxy-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-propenyloxy)-phenyl, 2-fluoro-4-cyano-5-hydroxy-phenyl, 2-fluoro-4-cyano-5-nitro-phenyl, 2-fluoro-4-cyano-5-diethoxyphosphorylamino-phenyl, 2-fluoro-4-cyano-5-chlorosulphonyl-phenyl, 2-fluoro-4-cyano-5-formylamino-phenyl, 2-chloro-4-cyano-5-ethoxycarbonyloxy-phenyl, 2-fluoro-4-cyano-5-diethoxy-Le A 32 986-Foreign Countries phosphorylinethoxy-phenyl, 2-chloro-4-cyano-S-hydroxy-phenyl, 2-fluoro-4-cyano-S-(N,N-diacetyl-amino)-phenyl, 2-fluoro-4-cyano-S-acetylamino-phenyl, 2-chloro-cyano-S-thiocyanato-phenyl, 2-fluoro-4-cyano-S-diethylaminooxy-phenyl, 2-fluoro-4-cyano-S-tetrahydrofuryloxy-phenyl, 2-fluoro-4-cyano-S-ureido-phenyl, 2-fluoro-4-S cyano-S-dimethoxymethyleneamino-phenyl, 2-chloro-4-cyano-S-ethoxymethylene-amino-phenyl, 2-fluoro-4-cyano-S-(2-chloro-ethoxycarbonyloxy)-phenyl, 2-chloro-cyano-S-dimethylaminomethylenamino-phenyl, 2-chloro-4-cyano-S-(perhydropyran-4-yloxy)-phenyl, 2-fluoro-4-cyano-S-(2-methoxycarbonyl-ethyl)-phenyl, 2-chloro-cyano-S-(2-carboxy-2-chloro-ethyl)-phenyl, 2-fluoro-4-cyano-S-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-S-(2-chloro-2-s-butoxycarbonyl)-phenyl, 2-fluoro-4-cyano-S-(2-chloro-2-carbamoyl-ethyl)-phenyl, 2-fluoro-4-cyano-S-(2-chloro-2-methoxycarbonyl-1-methyl-ethyl)-phenyl, 2-fluoro-4-cyano-S-(1,2-dibromo-2-methoxycarbonyl-ethyl)-phenyl, 2-chloro-4-cyano-S-(2-chloro-2-i-propoxy-carbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-S-(2-carboxy-2-chloro-ethyl)-1 S phenyl, 2-fluoro-4-cyano-S-(2-chloro-2-ethylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-S-(2-allylaminocarbonyl-2-chloro-ethyl)-phenyl, 2-fluoro-4-cyano-S-(2-ethoxycarbonyl-ethenyl)-phenyl, 2-fluoro-4-cyano-S-(2-chloro-2-cyclopropylamino-carbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-S-(2-chloro-2-dimethylaminocarbonyl-ethyl)-phenyl, 2-chloro-4-cyano-S-(2-chloro-2-ethylsulphonylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-thiocarbamoyl-S-(2-ethylaminocarbonyl-ethenyl)-phenyl, 2-fluoro-4-cyano-S-(1-ethoxycarbonyl-ethyl)-phenyl, 2-chloro-4-cyano-S-(1-ethoxy-carbonylethyl)-phenyl, 2-chloro-4-cyano-S-carboxy-phenyl, 2-fluoro-4-cyano-S-i-butoxy-phenyl, 2-chloro-4-cyano-S-i-butoxy-phenyl, 2-chloro-4-cyano-S-(2-methoxy-ethoxy)-phenyl, 2-fluoro-4-cyano-S-(N-acetyl-N-methylsulphonyl-amino)-phenyl, 2S fluoro-4-cyano-S-(N-propionyl-N-methylsulphonyl-amino)-phenyl, 2-fluoro-4-cyano-S-(N-i-butyroyl-N-methylsulphonyl-amino)-phenyl, 2-fluoro-4-cyano-S-(N-pivaloyl-N-methylsulphonyl-amino)-phenyl, 2-fluoro-4-cyano-S-(N-benzoyl-N-methylsulph-onyl-amino)-phenyl, 2-fluoro-4-cyano-S-(N-(4-methoxy-benzoyl)-N-methyl-sulphonyl-amino)-phenyl, 2-fluoro-4-cyano-S-(N-acetyl-N-ethylsulphonyl-amino)-phenyl, 2-fluoro-4-cyano-S-(N-propionyl-N-ethylsulphonyl-amino)-phenyl, 2-fluoro-4-cyano-S-(N-i-butyroyl-N-ethylsulphonyl-amino)-phenyl, 2-fluoro-4-cyano-S-(N-Le A 32 986-Foreign Countries pivaloyl-N-ethylsulphonyl-amino)-phenyl, 2-fluoro-4-cyano-S-(N-benzoyl-N-ethyl-sulphonyl-amino)-phenyl, 2-fluoro-4-cyano-5-(N-(4-methoxy-benzoyl)-N-ethyl-sulphonyl-amino)-phenyl, 2-fluoro-4-thiocarbamoyl-5-(N-acetyl-N-methylsulphonyl-amino)-phenyl, 2-fluoro-4-thiocarbamoyl-S-(N-propionyl-N-methylsulphonyl-S amino)-phenyl, 2-fluoro-4-thiocarbamoyl-5-(N-i-butyroyl-N-methylsulphonyl-amino)-phenyl, 2-fluoro-4-thiocarbamoyl-5-(N-pivaloyl-N-methylsulphonyl-amino)-phenyl, 2-fluoro-4-thiocarbamoyl-S-(N-benzoyl-N-methylsulphonyl-amino)-phenyl, 2-fluoro-4 thiocarbamoyl-5-(N-(4-methoxy-benzoyl)-N-methylsulphonyl-amino)-phenyl, 2-fluoro-4-thiocarbamoyl-5-(N-acetyl-N-ethylsulphonyl-amino)-phenyl, 2-fluoro-4-thiocarbamoyl-5-(N-propionyl-N-ethylsulphonyl-amino)-phenyl, 2-fluoro-thiocarbamoyl-S-(N-i-butyroyl-N-ethylsulphonyl-amino)-phenyl, 2-fluoro-4-thio-carbamoyl-5-(N-pivaloyl-N-ethylsulphonyl-amino)-phenyl, 2-fluoro-4-thio-carbamoyl-5-(N-benzoyl-N-ethylsulphonyl-amino)-phenyl, 2-fluoro-4-thio-carbamoyl-5-(N-(4-methoxy-benzoyl)-N-ethylsulphonyl-amino)-phenyl.
Grou 2 N-i Ar-N ~ CF3 W-2) O
Ar has here, for example, the meanings listed above in Group 1.
Group 3 N-i Ar-N ~ CF3 O H (~-3) Ar has here, for example, the meanings listed above in Group 1.

Le A 32 986-Foreign Countries Grou 4 N-Ar-N / CF3 (lA-4) S Ar has here, for example, the meanings listed above in Group 1.
Group 5 N-/
Ar-N
CF3 (IA-5) Ar has here, for example, the meanings listed above in Group 1.
Group 6 N-/
Ar-N
CF3 (~-6) O
Ar has here, for example, the meanings listed above in Group 1.
Group 7 CI
N-/
Ar-N / CF3 O

Le A 32 986-Foreign Countries Ar has here, for example, the meanings listed above in Group 1.
Group 8 N-Ar-N ~ CHF2 (~-8) O
Ar has here, for example, the meanings listed above in Group 1.
Gr_ oup 9 CI
N-Ar-N ~ CF3 Ar has here, for example, the meanings listed above in Group 1.
Group 10 N-i Ar-N / CF3 (IA-10) O
Ar has here, for example, the meanings listed above in Group 1.
Groin 11 N-Ar-N / CHFZ
(IA-11 ) Le A 32 986-Foreign Countries Ar has here, for example, the meanings-listed above in Group 1.
Group 12 N-Ar-N / CHFZ
(IA-12) O
Ar has here, for example, the meanings listed above in Group 1.
Group 13 N-Ar-N / CFZCI (IA-13) O
Ar has here, for example, the meanings listed above in Group 1.
Group 14 N-Ar-N ~ CFZCI
(IA-14) Ar has here, for example, the meanings listed above in Group 1.
Group 1 S

Le A 32 986-Foreign Countries N- -Ar-N / CFZCI
(IA-15) O
Ar has here, for example, the meanings listed above in Group 1.
Group 16 N-Ar-N ~ CF3 (IA-16) O Br Ar has here, for example, the meanings listed above in Group 1.
Group 17 N-/
Ar-N ~ CF3 (IA-17) O CI
Ar has here, for example, the meanings listed above in Group 1.
Group 18 N-/
Ar-N
(IA-18) O
Ar has here, for example, the meanings listed above in Group 1.

Le A 32 986-Foreign Countries Group 19 N-Ar-I~ ~ CH3 (IA-19) O
Ar has here, for example, the meanings listed above in Group 1.
Grou~20 N-Ar-N ~ CF3 (IA-20) Ar has here, for example, the meanings listed above in Group 1.
Group 21 N-Ar-N / CHF2 (IA-21 ) Ar has here, for example, the meanings listed above in Group 1.
Group 22 N-Ar-N / CF2CI
(IA-22) Le A 32 986-Foreign Countries Ar has here, for example, the meanings-listed above in Group 1.
Group 23 'zFs (IA-23) Ar has here, for example, the meanings listed above in Group 1.
Group 24 N-Ar-N ~ CF3 (IA-24) O Br Ar has here, for example, the meanings listed above in Group 1.
Group 25 N-/
Ar-N / CF3 (IA-25) Ar has here, for example, the meanings listed above in Group 1.
Group 26 COOCzH$
N-Ar-N ~ CF3 O CH3 (~-26) Le A 32 986-Foreign Countries Ar has here, for example, the meanings listed above in Group 1.
S Group 27 COOCZHS
N-Ar-N ~ CF3 (IA.27) O
Ar has here, for example, the meanings listed above in Group 1.
Group.2 8 COOH
N-i Ar-N ~ CF3 (IA-28) Ar has here, for example, the meanings listed above in Group 1.
Group 29 CN
N-Ar-N ~ CF3 (IA-29) Ar has here, for example, the meanings listed above in Group 1.

' Le A 32 986-Foreign Countries GrouQ 30 CN
N-Ar-N ~ CF3 (IA-30) O
Ar has here, for example, the meanings listed above in Group 1.
Groin 31 N-i Ar-N / CF3 (IA-31 ) Ar has here, for example, the meanings listed above in Group 1.
Group 32 N-Ar-N ~ CF3 (IA-32) O
Ar has here, for example, the meanings listed above in Group 1.
The novel substituted phenylpyridazinones of the general formula (I) are obtained when (a) halogenoarenes of the general formula (II) ' Le A 32 986-Foreign Countries R' X~
R2 (B) in which R1, R2 and R3 are as defined above and X 1 represents halogen are reacted with pyridazinones of the general formula (III) Rs ~N
I
Ra NCH (.III) O
in which R4, RS and R6 are as defined above, or with acid adducts or alkali metal salts of compounds of the formula (III) if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or when (b) arylhydrazines of the general formula (IV) Le A 32 986-Foreign Countries NHZ R' HN

in which R1, R2 and R3 are as defined above are reacted with 13-trihalomethyl-enones of the general formula (V) Rs O (V) R4 0x2)3 in which R4, RS and R6 are as defined above and X2 represents halogen, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence 1 S of a diluent, or when (c) hydrazonecarboxylic acids of the general formula (VI) Rs N R' N /
R
COOH ~ ~ 2 (VI) 'R
Rs Le A 32 986-Foreign Countries in which R1, R2, R3, R4, RS and R6 are as defined above are condensed with ring-closure, i.e. reacted with a dehydrating agent, S
or when (d) 2,4-disubstituted phenylpyridazinones of the general formula (Ia) Rs N R' N /
R ~ (Ia) O \ z R
in which R1, R2, R4, RS and R6 are as defined above are nitrated, i.e. reacted with a nitrating agent, or when (e) hydrazonecarbonyl compounds of the general formula (VII) Rs Rs ~ N R' I
O HN /
R2 (VII) in which R1, R2, R3, RS and R6 are as defined above Le A 32 986-Foreign Countries are reacted with alkoxycarbonylmethylenephosphoranes of the general formula (VIII) COOR
4 ~
R "P(C6H5)s (VIII) in which R4 is as defined above and R represents alkyl having 1 to 6 carbon atoms, or with trialkyl phosphonocarboxylates of the general formula (IX) COOR
R4' _PO(OR)2 in which R4 is as defined above and R represents alkyl having 1 to 6 carbon atoms, in each case optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.
The compounds of the general formula (I) can also be converted by other customary methods into other compounds of the general formula (I) according to the above definition, for example by nucleophilic substitution (e.g. R3: F -~ OH, SH, NH2, OCH3, NHS02CH3) or by further transformations of functional groups (e.g. R2:
F/CIBr -~ CN, CONH2 ~ CN, CN ~ CSNH2, N02 ~ NH2; R3: N02 -~ NH2, NH2 ~ F, C1, Br, CN, NHS02CH3, S02C1, OCH3 -~ OH, OH ~ OCHzCH=CHZ) -cf. also the Preparation Examples.

Le A 32 986-Foreign Countries ' -26-Using, for example, 4-fluoro-6-methyl-5-trifluoromethyl-pyridazin-3-one and 4,5-di-fluoro-2-methoxy-benzonitrile as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following formula scheme:

CH3 F F3C ~ N F
FsC ~ N F / -.. I N
I N~ + ~ I - HF F / I
F ~ H ~CN ~ O

Using, for example, 4,4,4-trichloro-3-methyl-2-difluoromethyl-crotonaldehyde and 4-cyano-2-fluoro-5-propargyloxy-phenylhydrazine as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following formula scheme:
F H
F H
F ~ F I ~N F
F ~O
+ / I - 3 HCI H C N /

H3C CCI3 ~ CN O
~CN
O
Using, for example, 2-chloro-3-chlorodifluoromethyl-4-oxo-2-butenoic acid N-(4-cyano-2-fluoro-5-methylsulphonylamino-phenyl)-hydrazone as starting material, the course of the reaction in the process (c) according to the invention can be illustrated by the following formula scheme:

Le A 32 986-Foreign Countries ' -27-H . H
CIF2C w N CIF2C ~ N F
F
i I I
N --~ N

\ CN CN
H~N~SOZ H~N~SO2 Using, for example, 2-(2-chloro-4-cyano-phenyl)-4,6-dichloro-5-pentafluoroethyl-pyridazin-3-one and nitric acid as starting materials, the course of the reaction in the process (d) according to the invention can be illustrated by the following formula scheme:
CI
F5C2 ~ N CI + HN03 F
CI / ~ - HZO
~CN CN
Using, for example, 3,3,3-trifluoro-2-oxo-propanal I-(4-cyano-2,5-difluorophenyl-hydrazone) and ethyl triphenylphosphoranylidene-acetate as starting materials, the course of the reaction in the process (e) according to the invention can be illustrated by the following formula scheme:
F3C~N F + COOC2H5 F3C ~ ~ N F
'OI N ~ ~ ~ N
I H P~C6H5~3 CN O ~ CN
F F
The formula (II) provides a general definition of the halogenoarenes to be used as starting materials in the process (a) according to the invention for preparing the ' . Le A 32 986-Foreign Countries compounds of the formula (I). In the formula (II), R1, R2 and R3 preferably or in particular have that meaning which has already been mentioned above, in the description of the compounds of the formula (I) to be prepared according to the invention, as being preferred or as being particularly preferred for R1, R2 and R3; X1 S preferably represents fluorine, chlorine or bromine, in particular 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).
The formula (III) provides a general definition of the pyridazinones further to be used as starting materials in the process (a) according to the invention. In the formula (III), R4, RS and R6 preferably have that meaning which has already been mentioned 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 R4, RS and R6.
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;
Monatsh. Chem. 120 (1989), 329).
The formula (IV) provides a general definition of the arylhydrazines to be used as starting materials in the process (b) according to the invention for preparing the compounds of the formula (I). In the formula (IV), R1, R2 and R3 preferably have that meaning which has already been mentioned 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 R1, R2 and R3.
The starting materials of the formula (IV) are known and/or can be prepared by processes known per se (cf. EP 370332).

Le A 32 986-Foreign Countries The formula (V) provides a general definition of the ~i-trihalogenomethyl-enones further to be used as starting materials in the process (b) according to the invention.
1n the formula (V), R4, RS and R6 preferably have that meaning which has already been mentioned above, in the description of the compounds of the formula (I) to be S prepared according to the invention, as being preferred, particularly preferred or very particularly preferred for R4, RS and R6; X2 preferably represents fluorine, chlorine or bromine, in particular chlorine.
The starting materials of the formula (V) are known and/or can be prepared by I O processes known per se (cf. DE 2706700).
The formula (VI) provides a general definition of the hydrazonecarboxylic acids to be used as starting materials in the process (c) according to the invention for preparing the compounds of the formula (I). In the formula (VI), Rl, R2, R3, R4, RS and I S preferably have that meaning which has already been mentioned 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 Rl, R2, R3, R4, RS and R6.
20 The starting materials of the formula (VI) are known and/or can be prepared by processes known per se (cf. WO 9639392).
The hydrazonecarboxylic acids of the general formula (VI) are obtained when arylhydrazines of the general formula (IV) RZ (.N) in which Le A 32 986-Foreign Countries R1, R2 and R3 are as defined above are reacted with ~i-carboxy-enones of the general formula (X) Rs (X) in which R4, RS and R6 are as defined above, if appropriate in the presence of a diluent, such as, for example, ethanol, and if appropriate in the presence of a reaction auxiliary, such as, for example, p-toluenesulphonic acid, at temperatures between 0°C and 100°C.
The formula (Ia) provides a general definition of the 2,4-disubstituted phenyl-pyridazinones to be used as starting materials in the process (d) according to the invention for preparing compounds of the formula (I). In the formula (Ia), R1, R2, R4, RS and R6 preferably have that meaning which has already been mentioned 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 R1, R2, R4, RS and R6.
The starting materials of the formula (Ia) are known and/or can be prepared by processes known per se (cf. the processes (a) to (c) according to the invention).
The formula (VII) provides a general definition of the hydrazonecarbonyl compounds to be used as starting materials in the process (e) according to the invention for preparing compounds of the formula (I). In the formula (VII), R1, R2, R3, RS
and R6 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) ' Le A 32 986-Foreign Countries according to the invention, as being preferred, particularly preferred or very particularly preferred for R1, R2, R3, RS and R6.
The starting materials of the formula (VII) are known and/or can be prepared by processes known per se (cf. WO 9707104).
Not yet known from the literature and, as novel compounds, part of the subject-matter of the present application, are the hydrazonecarbonyl compounds of the general formula (VIIa) Rs ~ N R' I
O HN
\ ~ R2_i (VIIa) Ra in which R1 represents fluorine, chlorine or bromine, 1 S R2-1 represents cyano, carbamoyl, thiocarbamoyl, or represents in each case optionally fluorine- andlor chlorine-substituted alkyl, alkoxy or alkylthio having in each case 1 or 2 carbon atoms, R3 represents the grouping -A1-A2-A3 in which Al represents a single bond, represents oxygen, sulphur, -SO-, -S02-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, Cl-C4-alkylsulphonyl orphenylsulphonyl, Le A 32 986-Foreign Countries ' -32-A1 furthermore represents in each case optionally fluorine-, chlorine- or bromine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-aza alkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cyclo alkenediyl or phenylene, A2 represents a single bond, represents oxygen, sulphur, -SO-, -S02-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, A2 furthermore represents in each case optionally fluorine-, chlorine- or bromine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-aza alkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cyclo I S alkenediyl or phenylene, A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkyl-thio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally fluorine- or chlorine-substituted alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinyl-amino or alkinyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups, represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, CI-C4-alkyl- and/or CI-C4-alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cyclo-alkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxy-carbonyl or cycloalkylalkoxycarbonyl having in each case 3 to 6 . Le A 32 986-Foreign Countries carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, Cl-C4-alkyl-, Cl-C4-halogenoalkyl-, Cl-C4-alkyloxy-, Cl-C4-halogenoalkyloxy-and/or C1-C4-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C 1-C4-alkyl, phenyl-C 1-C4-alkoxy, phenyloxycarbonyl or phenyl-C 1-C4-alkoxycarbonyl, A3 furthermore represents in each case optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, iso-thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-Cl-C4-alkyl, furyl-Cl-C4-alkyl, thienyl-Cl-C4-alkyl, oxa-zolyl-C1-C4-alkyl, isoxazole-Cl-C4-alkyl, thiazole-C1-C4-alkyl, pyri-dinyl-C1-C4-alkyl, pyrimidinyl-Cl-C4-alkyl, pyrazolylmethoxy, furyl-methoxy, represents perhydropyranylmethoxy or pyridylmethoxy, R5 represents hydrogen, cyano, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine-andlor chlorine-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkyl-amino having in each case 1 to 4 carbon atoms in the alkyl groups, and R6 represents hydrogen, cyano, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine-and/or chlorine-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkyl-amino having in each case 1 to 4 carbon atoms in the alkyl groups.
The novel hydrazonecarbonyl compounds of the general formula (VIIa) are obtained when (a) arylhydrazines of the general formula (Na) Le A 32 986-Foreign Countries ' -34-N H2 R' HN
\ ~ Rz_~
(IVa) in which R1, R2-1 and R3 are as defined above are reacted with a-dihalogeno-carbonyl compounds of the general formula (XI) Rs X3 (XI) O
in which RS and R6 are as defined above and X3 represents halogen (in particular chlorine or bromine), if appropriate in the presence of a diluent, such as, for example, water, and if appropriate in the presence of a reaction auxiliary, such as, for example, sodium acetate, at temperatures between 0°C and 100°C (cf. the Preparation Examples), or when - in the case that R6 represents hydrogen -(~3) arylamines of the general formula (XII) R' \ ~ R2_~
(XII) Le A 32 986-Foreign Countries ' -35-in which Rl, R2-1 and R3 are as defined above are diazotized in a customary manner (for example by reaction with sodium nitrite and hydrochloric acid and/or acetic acid), the resulting diazonium compounds are reacted in a customary manner with 1,3-dicarbonyl compounds of the general formula (XIII) O O
R5'J v _OR
in which RS is as defined above and R represents alkyl (preferably methyl or ethyl) and the resulting compounds of the general formula (XIV) O OR

~ N R' I
O HN
\ ~ R2_~ (XIV) in which R, R1, R2-1 , R3 and RS are as defined above are hydrolyzed and decarboxylated in a customary manner.
The formulae (VIII) and (IX) provide general definitions of the alkoxycarbonylmethylenephosphoranes and trialkyl phosphonocarboxylates, -, ~ Le A 32 986-Foreign Countries respectively, furthermore required as starting materials in the process (e) according to the invention for preparing compounds of the fornmla (I). In the formulae (VIII) and (IX), R4 in each case preferably has that meaning which has already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for R4; R in each case preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.
The starting materials of the formulae (VIII) and (IX) are known chemicals for synthesis.
The processes (a), (b), (c), (d) and (e) according to the invention for preparing the compounds of the formula (I) are preferably carried out in the presence of a diluent.
Suitable diluents are, in general, the customary organic solvents. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, benzine, 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 ether or ethylene glycol diethyl ether, diethylene glycol dimethyl ether or diethylene glycol diethyl ether; dialkyl ketones, such as, for example, acetone, butanone (methyl ethyl ketone), methyl i-propyl ketone or methyl i-butyl ketone, nitriles, such as, for example, acetonitrile, propionitrile, butyronitrile or benzonitrile; amides, such as, for example, N,N-dimethyl-formamide (DMF), N,N-dimethyl-acetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphoric triamide; esters, such as, for example, methyl acetate, ethyl acetate, -n- or -i-propyl acetate, -n-, -i- or -s-butyl acetate; sulphoxides, such as, for example, dimethyl sulphoxide; alkanols, such as, for example, methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, diethylene glycol Le A 32 986-Foreign Countries monomethyl ether or diethylene glycol ~monoethyl ether; mixtures thereof with water or pure water. In the process (b) according to the invention it is advantageously also possible to use acetic acid as diluent.
S The processes (a), (b) and (e) according to the invention for preparing the compounds of the formula (I) are preferably carried out in the presence of a suitable reaction auxiliary. Suitable reaction auxiliaries are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diaza-bicyclo[2,2,2]-octane (DABCO), 1,5-diazabicyclo[4,3,0]-non-S-ene (DBN), and 1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU).
The process (c) according to the invention for preparing the compounds of the formula (I) is carried out in the presence of a dehydrating agent. Suitable dehydrating agents are the customary dehydrating agents, such as, for example, sulphuric acid, methanesulphonic acid, benzenesulphonic acid, p-toluenesulphonic acid, acetic anhydride and phosphorus (V) oxide.

Le A 32 986-Foreisn Countries The process (d) according to the invention for preparing the compounds of the formula (n is carried out using a nitrating agent. Suitable nitrating agents are the customary nitrating agents, such as, for example, nitric acid and its mixtures with nitrating auxiliaries, such as, for example, sulphuric acid.
When carrying out the processes (a), (b), (c), (d) and (e) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at 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 carned out under atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - in general between 0.1 bar and 10 bar.
For carrying out the processes (a), (b), (c), (d) and (e) according to the invention, the starting materials are generally employed in approximately equimolar amounts.
However, it is also possible to use a relatively large excess of one of the components.
The reaction is generally carried out in a suitable diluent, if appropriate in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples).
The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest sense there are to be understood all plants which grow in locations where they are undesired. 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 connection with the following plants:
Dicotyledonous weeds of the e~ nera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Le A 32 986-Foreign Countries Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dico~rledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monocotyledonous weeds of the eg nera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
Monocotyledonous crops of the eg nera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
Depending on the concentration, the compounds are suitable for total weed control, for example on industrial terrain and rail tracks and on paths and areas with or without tree growth. Equally, the compounds can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns and turf and pastures and for selective weed control in annual crops.

Le A 32 986-Foreign Countries The compounds of the formula (n according to the invention have strong herbicidal activity and a broad activity spectrum when applied to the soil and to 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, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid Garners, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers.
If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Liquid solvents which are mainly suitable are:
aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.
Suitable solid Garners are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid Garners for granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic meals, and granules of organic Le A 32 986-Foreign Countries material, such as sawdust, coconut shells, maize cobs and tobacco stalks;
suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, S arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use colorants, such as inorganic pigments, for example iron oxide, 1 S titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Possible components for the mixtures are known herbicides, for example acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulphuron, anilofos, asulam, atrazine, azafenidin, azimsulphuron, benazolin(-ethyl), benfuresate, bensulphuron(-methyl), bentazone, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide, Le A 32 986-Foreign Countries bromofenoxim, bromoxynil, butachlor, -butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulphuron, chlortoluron, cinidon(-ethyl), cinmethylin, cinosulphuron, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulphuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulphamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulphuron(-methyl), ethofumesate, ethoxyfen, ethoxysulphuron, etobenzanid, fenoxaprop(-P-ethyl), flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulphuron, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulphuron(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulphuron, iodosulphron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin, metsulphuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulphuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulphuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulphuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulphocarb, prosulphuron, pyraflufen(-ethyl), pyrazolate, pyrazosulphuron(-ethyl), pyrazoxyfen, pyribenzoxim, Le A 32 986-Foreign Countries pyributicarb, pyridate, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulphuron, sethoxydim, simazine, simetryn, sulcotrione, sulphentrazone, sulphometuron(-methyl), sulphosate, sulphosulphuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulphuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulphuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulphuron.
A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, 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 customary manner, for example by watering, spraying, atomizing, scattering.
The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and S kg per ha.
The preparation and the use of the active compounds according to the invention can be seen from the examples below.

. Le A 32 986-Foreign Countries Preparation Examples:
Example 1 ~N F
N \
O
'CN
F
5.0 g (18 mmol) of 3,3,3-trifluoro-2-oxo-propanal-1-(2,5-difluoro-4-cyano-phenyl-hydrazone) in 150 ml of toluene are admixed with 8.7 g (26 mmol) of methyl (triphenylphosphoranylidene)acetate, and the mixture is stirred at reflux temperature for 3 hours. The mixture is concentrated using a rotary evaporator, and the residue is recrystallized from isopropanol.
This gives 1.3 g (24% of theory) of 2-(2,5-difluoro-4-cyano-phenyl)-S-trifluoro-methyl-pyridazin-3-one of melting point 143°C.
Example 2 ~N F
HaC N ~ \
O /
CN
F
5.0 g (18 mmol) of 3,3,3-trifluoro-2-oxopropanal-1-(2,5-difluoro-4-cyano-phenyl-hydrazone) in 150 ml of toluene are admixed with 9.4 g (26 mmol) of (1-ethoxy-carbonylethylidene)triphenylphosphorane, and the mixture is stirred at reflux temperature for 3 hours. The mixture is concentrated using a rotary evaporator and the residue is recrystallized from isopropanol.

Le A 32 986-Foreign Countries This gives 2.41 g (42.5% of theory) of 2-(2,5-difluoro-4-cyano-phenyl)-4-methyl-5-trifluoromethyl-pyridazin-3-one of melting point 135°C.
Analogously to Example 1 and 2, and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare the compounds of the formula (I) listed in Table 1 below.
Rs Rs I ~ N R' O I / R2 (I) Table 1: Examples of the compounds of the formula (I) Ex.
No. R1 R2 R3 R4 RS R6 4 Cl CN N02 H CF3 H

6 Cl CN N02 H CF3 CH3 8 Cl CN N02 CH3 CF3 H
9 Cl CN OH H CF3 H
13 F CN OCH(CH3)2 CH3 CF3 H

Le A 32 986-Foreign Countries Ex.
No. Rl R2 R3 R4 RS R6 14 F CN OCH2CH=CH2 CH3 CF3 H

S

16 F CN OCH(CH3)C---CH CH3 CF3 H

19 F CN OCH2COOCH(CH3)2 CH3 CF3 H

20 F CN OCH2COOCSH" CH3 CF3 H

21 F CN OCH(CH3)COOC2H5 CH3 CF3 H

25 F CN OCH(CH3)z H CF3 H

26 F CN OCH2CH=CH2 H CF3 H

27 F CN OCHZC=CH H CF3 H

28 F CN OCH(CH3)C=CH H CF3 H

31 F CN OCH2COOCH(CH3)2 H CF3 H

32 F CN OCH2COOCSH" H CF3 H

33 F CN OCH(CH3)COOC2H5 H CF3 H

35 F CN COOCzHs H CF3 H

37 F CN CON(CH3)z CH3 CF3 H

Le A 32 986-Foreign Countries Ex.
No. R' R2 R3 R RS R6 44 F CN NHS02cyclopropyl CH3 CF3 H

49 F CN NHS02cyclopropyl H CF3 H

50 Cl CN NH2 H CF3 H

S Cl CN OCH2C---CH H CF3 H

52 Cl CN OCH(CH3)C---CH H CF3 H

55 C1 CN OCH2COOCH(CH3)2 H CF3 H

56 Cl CN OCHZCOOCSH~ 1 H CF3 H

57 Cl CN NHSOZCH3 CH3 CF3 H

58 Cl CN NHSOZC2H5 CH3 CF3 H

59 C1 CN OCH2C=CH CH3 CF3 H

60 Cl CN OCH(CH3)C---CH CH3 CF3 H

61 Cl CN OCH2COOCH3 CH3 CF3 H

63 Cl CN OCHZCOOCH(CH3)2 CH3 CF3 H

64 Cl CN OCHZCOOCSH" CH3 CF3 H

65 F CSNHz NHSOzCH3 CH3 CF3 H

66 F CSNHz NHS02C2H5 CH3 CF3 H

Le A 32 986-Foreign Countries Ex. -No. R' R2 R3 R4 RS R6 69 Cl CSNH2 OCH(CH3)C---CH CH3 CF3 H

70 Cl CSNH2 OCH2COOCSH~, CH3 CF3 H

71 F CSNH2 OCH2CH=CH2 H CF3 H

73 F CSNH2 OCH(CH3)C---CH H CF3 H

74 Cl CSNH2 NHS02CH3 H CF3 H

75 Cl CSNH2 NHS02C2H5 H CF3 H

76 F CSNH2 OCH2CH=CH2 CH3 CF3 H

78 F CSNH2 OCH(CH3)C---CH CH3 CF3 H

79 Cl CSNH2 NHSOZCH3 CH3 CF3 H

80 Cl CSNH2 NHS02CzH5 CH3 CF3 H

81 F CN N(S02CH3)z CH3 CF3 H

82 F CN N(S02C2H5)z CH3 CF3 H

83 F CN N(CH3)S02CH3 CH3 CF3 H

84 F CN N(CH3)S02C2H5 CH3 CF3 H

85 F CSNHZ N(SOzCH3)2 CH3 CF3 H

86 F CSNH2 N(S02CzH5)2 CH3 CF3 H

91 F CF3 OCH2CH=CHZ CH3 CF3 H

92 F CF3 OCH2C=CH CH3 CF3 H

93 F CF3 OCH2COOCSH,1 CH3 CF3 H

94 F CSNH2 N(CH3)SOZCH3 CH3 CF3 H

Le A 32 986-Foreign Countries Ex.
No. Rl R2 R3 R4 RS R6 95 F CSNH2 N(CH3)S02C2H5 CH3 CF3 H

96 F CSNH2 N(S02CH3)z CH3 CF3 H

97 F CSNH2 N(S02C2H5)2 CH3 CF3 H

98 F CN OCH2CH=CH2 H CF3 CH3 100 F CN OCH(CH3)C--__CH H CF3 CH3 103 F CN OCH2COOCH(CH3)2 H CF3 CH3 104 F CN OCH2COOCSH1, H CF3 CH3 105 F CN OCH(CH3)COOC2H5 H CF3 CH3 Le A 32 986-Foreign Countries Ex.

No. R' R2 R3 R4 RS R6 \
~

N
I

~SOz H C

\
~

N
I

SO
z HsCi 123 F CN CHs CH3 CF3 H

\NiSOz I

SO

HsCz \N I \

SOz /

\N
I

SO
H
Cz z S

\N
I

SOz HSCZ
CI

\N
I

SO CI
/ z HsCz Le A 32 986-Foreign Countries Ex.
No. R' R2 R3 R4 RS R6 ~N~
I
/SOz HsCz 131 F CN OCH(CH3)COOCH(CH3)2 CH3 CF3 H

132 F CN OCH(C2H5)COOCH(CH3)2CH3 CF3 H

135 F CN OCH(C2H5)COOCH3 CH3 CF3 H

136 F CN OCH(C2H5)COOC2H5 CH3 CF3 H

137 F CN OCH(CH3)COOCH3 CH3 CF3 H

139 F CN O~ H CF3 H

140 F CN O~ CH3 CF3 H

141 F CN O~ H CF3 CH3 142 F CN O~ CH3 CF3 CH3 143 F CN O~ H CF3 H

144 F CN O~ CH3 CF3 H

145 F CN O~ H CF3 CH3 Le A 32 986-Forei~~n Countries Ex.

No. R' R2 R3 R4 RS R6 146 F CN O~ CH3 CF3 CH3 147 F CN O ~ H CF3 H

O

148 F CN ~ CH3 CF3 H

O

149 F CN ~ H CF3 CH3 O

150 F CN ~ CH3 CF3 CH3 151 F CN I , H CF3 H

CI

O
152 F CN I , CH3 CF3 H

CI

O

153 F CN I , H CF3 CH3 CI

O

154 F CN I , CH3 CF3 CH3 CI

155 F CN O ~ I CH3 CF3 H

O

O~O \

O
/

O
, Le A 32 986-Foreign Countries Ex.
No. R' R2 R3 R4 RS R6 158 F CN o~o \
O ~ , CH3 CF3 H
O~O \
159 F CN O ~ / CH3 CF3 CH3 160 F CN O O \ I H CF3 H
O
i 161 F CN O O \ I CH3 CF3 H
O
162 F CN O O \ I H CF3 CH3 O
163 F CN O O \ ( CH3 CF3 CH3 O
O~O~CH
164 F CN O\ 3 H CF3 H

O~O~CH3 165 F CN O\ CH3 CF3 H

O~O~CH3 166 F CN O\ H CF3 CH3 O~O~CH3 167 F CN O\ CH3 CF3 CH3 Le A 32 986-Foreign Countries Ex.

No. R' R2 R3 R4 RS R6 O' O~
CzHS

168 F CN o\ H CF3 H

CzHs O~O~CzHs 169 F CN o\ CH3 CF3 H

CzHs O~O\CzHS

170 F CN o\ H CF3 CH3 CzHs O~O'CzHs -171 F CN o' CH3 CF3 CH3 CzHs O
172 F CN o/J , H CF3 H

173 F CN o~~ CH3 CF3 H

O
174 F CN o~~ H CF3 CH3 O
175 F CN o~~ CH3 CF3 CH3 ~/O

O
176 F CN O~ H CF3 H
J

O
o 177 F CN ~ CH3 CF3 H
J

O

178 F CN ~ H CF3 CH3 J

O

~ CH3 CF3 CH3 O

Le A 32 986-Foreign Countries Ex. -No. R' R2 R3 R4 Rs R6 O O
180 F CN ~ H CF3 H
J

O o 181 F CN ~ CH3 CF3 H
J

O o -182 F CN ~ H CF3 CH3 J

O O

183 F CN ~ CH3 CF3 CH3 J

184 F CN O~CHO H CF3 H

185 F CN O~CHO CH3 CF3 H

186 F CN O~CHO H CF3 CH3 187 F CN O~CHO CH3 CF3 CH3 O

O

O

O

O -192 F CN O~O~ H CF3 H

O

193 F CN O~O~ CH3 CF3 H

Le A 32 986-Foreign Countries Ex.

No. R' R2 R3 R4 RS R6 O

194 F CN O O~ H CF3 CH3 O

195 F CN O O~ CH3 CF3 CH3 O
196 F CN p~ ~ H CF3 H
O

O
197 F CN O~ ~ CH3 CF3 H
O

198 F CN O~ ~ H CF3 CH3 O

O
199 F CN O~ ~ CH3 CF3 CH3 O

O
200 F CN O~ ~ H CF3 H

O

O
201 F CN O~ ~ CH3 CF3 H

O

O
202 F CN O~ ~ H CF3 CH3 O

O
203 F CN O~ CH3 CF3 CH3 ~

O

O

204 F CN O O~ H CF3 CH3 O

205 F CN O~O~ CH3 CF3 H
I

Le A 32 986-Foreign Countries Ex.
No. Rl R2 R3 R4 RS R6 O
206 F CN O O~ H CF3 CH3 O
207 F CN O O~ CH3 CF3 CH3 O
208 F CN O~N~CH3 H CF3 H
H
O
209 F CN O~N~CH3 CH3 CF3 H
H
O
210 F CN O~N~CH3 H CF3 CH3 H
O
211 F CN O~N~CH3 CH3 CF3 CH3 H
O
212 F CN O H~CH3 H CF3 H

O
213 F CN O H'CH3 CH3 CF3 H

O
214 F CN O~N~CH3 H CF3 CH3 H

O
21 S F CN O~N~CH3 CH3 CF3 CH3 H

Le A 32 986-Foreign Countries Ex.
No. R' R2 R3 R4 RS R6 O
216 F CN O N~CH(CH3)Z H CF3 H
H

O
217 F CN O N~CH(CH3)2 CH3 CF3 H
H

O
218 F CN O N~CH(CH3)2 H CF3 CH3 H

O
219 F CN O N~CH(CH3)z CH3 CF3 CH3 H

O
220 F CN O~N~Q H CF3 H
H
O
221 F CN O~N~ CH3 CF3 H
H
O
222 F CN O~N~ H CF3 CH3 H
O
223 F CN O~N~Q CH3 CF3 CH3 H
O
224 F CN O N~ H CF3 H
H

O
225 F CN O~H~ CH3 CF3 H

Le A 32 986-Foreign Countries Ex.
No. RI R2 R3 R4 RS R6 O
226 F CN ~ H~ H CF3 CH3 O
227 F CN ~ H~ CH3 CF3 CH3 O
O ' 228 F CN H / ~ H CF3 H

O
O
229 F CN CH H / ~ CH3 CF3 H

O
O
230 F CN ~N H CF CH
H ~ ~ 3 3 O
O
231 F CN H / ~ CH3 CF3 CH3 O
232 F CN ~ N(CH3)2 H CF3 H

O
233 F CN ~ N(CH3)Z CH3 CF3 H

O
234 F CN ~~N(CH3)2 H CF3 CH3 Le A 32 986-Foreign Countries Ex.

No. R' R2 R3 R4 RS R6 O

235 F CN ~~N(CH3)2 CH3 CF3 CH3 O

236 F CN O N(C2H5)Z H CF3 H

O

237 F CN ~~N(CZHS)2 CH3 CF3 H

O

238 F CN O Y 'N(CZHS)2 H CF3 CH3 ' O

239 F CN O Y 'N(CZHS)z CH3 CF3 CH3 I

O

240 F CN C~N~ H CF3 H
I H

O

241 F CN ~~N~ CH3 CF3 H
H

O

242 F CN ~~N~ H CF3 CH3 ' H

O

243 F CN C~N~ CH3 CF3 CH3 H

Le A 32 986-Foreman Countries Ex.

No. Rl R2 R3 R4 RS R6 O

244 F CN O H~OH H CF3 H

O

245 F CN O H~OH CH3 CF3 H

O

246 F CN O H~OH H CF3 CH3 O

247 F CN O H~OH CH3 CF3 CH3 O

248 F CN O~N~O~CH3 H CF3 H
(~

H

O

249 F CN O~N~O~CH3 CH3 CF3 H
II

H

O

250 F CN O H~O~CH3 H CF3 CH3 I I

O

O

251 F CN O~N~O CH3 CH3 CF3 CH3 H

O

252 F CN O~N~ H CF3 H
I H

Le A 32 986-Foreign Countries Ex. -No. R' R2 R3 R4 RS R6 O
253 F CN O H~ CH3 CF3 H

O -254 F CN O H~ H CF3 CH3 O
255 F CN O H~ CH3 CF3 CH3 256 F CN OC3H~-n CH3 CF3 H
O
O
257 F CN ~ ~ CH3 CF3 H
CI
O
258 F CN O O~CH3 CH3 CF3 H

~O N~
259 F CN ~ S02 CH3 CF3 H
O
260 F CN ~ N \ ~ CH3 CF3 H

O
261 F CN O~ C H H CF3 H
2 s Le A 32 986-Foreign Countries The compound listed above in Table 1 as Example 10 can, for example, be prepared as follows:
F3C ~ ~ N F
N

C I ~ CN
~~H
S 2.0 g (6.1 mmol) of 2-(4-cyano-2-fluoro-5-methoxy-phenyl)-4-methyl-5-trifluoro-methyl-pyridazin-3-one in 100 ml of dichloromethane are admixed with 18.4 g (18.3 mmol) of boron tribromide (1 molar solution in dichloromethane), the mixture is stirred at 25°C for 16 hours, 150 ml of water are then added slowly and the organic phase is dried over sodium sulphate and concentrated using a rotary evaporator.
This gives 1.8 g (94% of theory) of 2-(4-cyano-2-fluoro-5-hydroxy-phenyl)-4-methyl-5-trifluoromethyl-pyridazin-3-one of melting point 189°C.
The compound listed above in Table 1 as Example 11 can, for example, be prepared as follows:
F3C ~ ~ N F
N

C ~ ~ CN
~~CH3 3.9 g (13.5 mmol) of 3,3,3-trifluoro-2-oxopropanal-1-(4-cyano-2-fluoro-S-methoxy-phenylhydrazone) in 150 ml of toluene are admixed with 7.0 g (19.3 mmol) of (1-ethoxycarbonyl-ethylidene)-triphenylphosphorane, and the mixture is stirred under argon at reflux temperature for 2 hours. After concentration using a rotary evaporator, the residue is recrystallized from isopropanol.

Le A 32 986-Foreign Countries This gives 2.2 g (50% of theory) of 2-(4-cyano-2-fluoro-5-methoxy-phenyl)-4-methyl-S-trifluoromethyl-pyridazin-3-one of melting point 178°C.
The compound listed above in Table 1 as Example 13 can, for example, be prepared as follows:
F3C ~ ~ N F
N

~ CN
~~CH(CH3)2 3.8 g (8 mmol) of 2-(4-bromo-2-fluoro-5-isopropoxy-phenyl)-4-methyl-S-trifluoro-methyl-pyridazin-3-one are dissolved in 10 ml of N-methyl-pyrrolidone, admixed with 0.9 g (9.6 mmol) of copper(I) cyanide and heated under reduced pressure (0.1 mbar) at 90°C, with distillative removal of 2 ml of solvent. The mixture is then heated under atmospheric pressure (under argon) to 170°C and stirred at this temperature for 6 hours. After cooling to 20°C, the mixture is stirred with 100 ml of ethyl acetate, admixed with 10% strength ammonia solution and filtered. The filtrate is washed with water, dried with sodium sulphate and carefully concentrated under waterpump vacuum.
This gives 3.0 g (89% of theory) of 2-(4-cyano-2-fluoro-5-isopropoxy-phenyl)-4-methyl-S-trifluoromethyl-pyridazin-3-one as crude product (content: 85%
according to HPLC).
For further purification, 2 g of this crude product are chromatographed over silica gel using dichloromethane. This gives the pure product (0.7 g, content: 97%
according to HPLC) of melting point 121 °C.

Le A 32 986-Foreign Countries The compound listed above in Table 1 as Example 1 S can, for example, be prepared as follows:
N
S
0.6 g (1.9 mmol) of 2-(4-cyano-2-fluoro-5-hydroxy-phenyl)-4-methyl-S-trifluoro-methyl-pyridazin-3-one in 30 ml of N,N-dimethyl-formamide are stirred at 25°C with 0.4 g (3 mmol) of potassium carbonate and 0.31 g (2.1 mmol) of propargyl bromide (80% pure) for 60 minutes, and the mixture is then admixed with water and adjusted to pH 6 using conc. hydrochloric acid, and precipitated product is filtered off with suction, washed with water and dried. For purification, the product is recrystallized from isopropanol.
This gives 0.3 g (44% of theory) of 2-(4-cyano-2-fluoro-S-propargyloxy-phenyl)-methyl-5-trifluoromethyl-pyridazin-3-one of melting point 145°C.
The compound listed above in Table 1 as Example 18 can, for example, be prepared as follows:

~~N F
N

O ~ /
~CN
O
O ~O-CZHS

Le A 32 986-Foreign Countries 0.7 g (2.24 mmol) of 2-(4-cyano-2-fluoro-5-hydroxy-phenyl)-4-methyl-5-trifluoro-methyl-pyridazin-3-one in 30 ml of N,N-dimethyl-formamide are stirred at 25°C with 0.48 g (3.5 mmol) of potassium carbonate and 0.42 g (2.5 mmol) of ethyl bromoacetate for 60 minutes, the mixture is then admixed with water and adjusted to pH 6 using conc. hydrochloric acid, and precipitated product is filtered off with suction, washed with water and dried.
This gives 0.64 g (71 % of theory) of 2-[4-cyano-5-(ethoxycarbonylmethoxy)-2-fluoro-phenyl]-4-methyl-5-trifluoromethyl-pyridazin-3-one of melting point 95°C.
The compound listed above in Table 1 as Example 41 can, for example, be prepared as follows:
F3C ~ ~ N F
N

O ~ ~ CN
,NH

5.5 g (15 mmol) of 3,3,3-trifluoro-2-oxo-propanal-1-(4-cyano-5-ethylsulphonyl amino-2-fluoro-phenylhydrazone) in 100 ml of toluene are admixed with 8.2 g (22.5 mmol) of (1-ethoxycarbonyl-ethylidene)-triphenylphosphorane, and the mixture is stirred under argon at reflux temperature for 2 hours. After concentration using a rotary evaporator, the residue is chromatographed over silica gel using toluene/ethyl acetate 3:1.
This gives 3.6 g (59.5% of theory) of 2-(4-cyano-5-ethanesulphonamino-2-fluoro-phenyl)-4-methyl-5-trifluoromethyl-pyridazin-3-one of melting point 198°C.
The compound listed above in Table 1 as Example 66 can, for example, be prepared as follows:

Le A 32 986-Foreign Countries F3r 1.6 g (4 mmol) of 2-(4-cyano-5-ethylsulphonylamino-2-fluoro-phenyl)-4-methyl-S-trifluoromethyl-pyridazin-3-one are initially charged in 30 ml of pyridine and 12 ml of triethylamine and, at 60-70°C, hydrogen sulphide is introduced underneath the surface of the liquid for 90 minutes. After the reaction has ended, the mixture is flushed with nitrogen for 60 minutes, cooled to 25°C and stirred with ice-water, precipitated product is filtered off with suction and the residue is washed with water and dried.
This gives 0.9 g (51% of theory) of 2-(2-fluoro-5-ethylsulphonylamino-4-thio-carbamoyl-phenyl)-4-methyl-5-trifluoromethyl-pyridazin-3-one of melting point 88°C
The compound listed above in Table 1 as Example 122 can, for example, be prepared as follows:
F3C I ~ N F
N

O I ~ CN
N
HSCZ S0 ~ -2 O
1.2 g (3 mmol) of 2-(4-cyano-S-ethylsulphonylamino-2-fluoro-phenyl)-4-methyl-5-trifluoromethyl-pyridazin-3-one in 50 ml of acetonitrile are admixed with 0.6 g (6 mmol) of triethylamine and 0.77 g (6 mmol) of 3-chloro-propionyl chloride, and the mixture is stirred at 25°C for 12 hours. After concentration using a rotary H5C2 S02 ' Le A 32 986-Foreign Countries evaporator, the residue is stirred with-water and acidified with conc.
hydrochloric acid, and precipitated product is filtered off with suction, washed with water and dried.
This gives 1.1 g of (2-[5-(N-ethenylcarbonyl-N-ethylsulphonylamino)-4-cyano-2-fluoro-phenyl]-4-methyl-5-trifluoromethyl-pyridazin-3-one of melting point 96°C.
The compound listed above in Table 1 as Example 129 can, for example, be prepared as follows:

F3C ~ ~ N F
N

O ~ ~ CN
,NH

1.22 g (3.2 mmol) of 1-[(4-cyano-S-methylsulphonylamino-2-fluoro-phenyl)-hydrazono]-3-ethoxycarbonyl-1-chloro-1,1-difluoro-propan-2-one in 50 ml of toluene are admixed with 1.74 g (4.8 mmol) of (1-ethoxycarbonyl-ethylidene)-triphenyl-1 S phosphorane, and the mixture is stirred under argon at reflux temperature for 2 hours.
After concentration using a rotary evaporator, the residue is chromatographed over silica gel using toluene/ethyl acetate 3:1.
This gives 0.2 g (15% of theory) of 2-(4-cyano-S-ethanesulphonamino-2-fluoro-phenyl)-4,6-dimethyl-5-trifluoromethyl-pyridazin-3-one of melting point 191 °C.
The compound listed above in Table 1 as Example 107 can, for example, be prepared as follows:

' Le A 32 986-Forei~ Countries -Hs F3C ~ ~ N F
N
C ~ ~ CN
,NH

1.22 g (3.2 mmol) of 1-[(4-cyano-5-methylsulphonylamino-2-fluoro-phenyl)-hydrazono]-3-ethoxycarbonyl-1-chloro-1,1-difluoro-propan-2-one in 50 ml of toluene are admixed with 1.7 g (4.8 mmol) of (1-ethoxycarbonyl-methylidene)-triphenyl-phosphorane, and the mixture is stirred under argon at reflux temperature for 2 hours.
After concentration using a rotary evaporator, the residue is chromatographed over silica gel using toluene/ethyl acetate 3:1.
This gives 0.2 g (15.5% of theory) of 2-(4-cyano-5-ethylsulphonylamino-2-fluoro-phenyl)-6-methyl-5-trifluoromethyl-pyridazin-3-one of melting point 143°C.
Physical data for compounds listed in Table 1 are listed in Table 1 a below.

Le A 32 986-Foreign Countries Table 1 a:
Ex. No. Physical data 10 m.p.: 189C

log.P = 2.27 a~

m.p.: 178C

log.P = 2.76 a~

12 log.P = 3.12 a~

m.p.: 121C

log.P = 3.40 a~

log.P = 3.24 a' NMR(CDC13): 2.44-2.45; 4.65-4.68; 7.46-7.49;
8.03 ppm m.p.: 145C

Iog.P = 2.92 a~

m.p.: 95C

Iog.P = 3.04 a~

21 m.p.: 118C

m.p.: 174C

log.P = 2.41 a~

m.p.: 140C

log.P = 2.76 a~

m.p.: 202C

log.P = 2.91 a~

m.p.: 198C

log.P = 2.42 a~

46 m.p.: 174C

m.p.: 88C

Iog.P = 2.44 a~

m.p.: 98C

Iog.P = 2.68 a~

Le A 32 986-Foreign Countries Ex. No. Physical data m.p.: 143C

log.P = 2.31 a) 112 m.p.: 160C

m.p.: 183C

log.P = 2.43 a) m.p.: 149C

log.P = 2.70~a) m.p.: 95C

log.P = 2.89 a) 123 m.p.: 220C

m.p.: 135C

log.P = 3.39 a) 125 log.P = 3.03 a) m.p.: 165C

log.P = 3.29 a) m.p.: 116C

log.P = 2.97 a) 128 m.p.: 131 C

m.p.: 189C

log.P = 2.65 a) m.p.: 142C

log.P = 1.94 a) log.P = 3.62 a~

131 NMR(CDC13): 1.17-1.19; 1.25-1.27; 1.70-1.72;
2.43;

4.72-4.78; 6.94-6.96; 7.99 m log.P = 3.93 a) 132 NMR(CDC13): 1.13-1.26; 2.04-2.13; 2.43;
4.56-4.60;

7.46-7.49 m Le A 32 986-Foreign Countries Ex. No. Physical data 133 m.p.: 134C

134 m.p.: 60C

135 NMR(CDC13): 2.43-2.44; 3.77; 4.61-4.63;
8.01 ppm ~(CDC13): 2.07-2.12; 2.43-2.44; 4.19-4.24;
7.46-7.49; 8.00 ppm NMR(CDCl3): 1.72-1.74; 2.36; 4.77-4.82;
7.47-7.50;

8.01 ppm 138 NMR(CDC13): 2.44-2.46; 4.93; 7.55-7.58;
8.05 ppm log.P = 3.51 NMR(CDC13): 2.44-2.54; 5.03; 7.26; 8.03 ppm m.p.: 83C

log.P = 3.65 256 m.p.: 97C

m.p.: 22 I C

log.P = 4.17 log.P = 4.64 258 NMR(CDC13):1.54-I.55; 1.99-2.09;

2.42-2.44;4.25-4.26; 6.91-6.93 ppm m.p.: 161C

log.P = 3.10 log.P = 2.93 260 NMR(CDC13): 1.49-1.54; 2.01; 2.44-2.46;

4.51-4.52; 7.60-7.63; 8.05 ppm m.p.:

log.P = 2.91 Le A 32 986-Forei~~n Countries The loge values given above in Table 1 were determined in accordance with EEC
Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reverse-phase column (C 18). Temperature: 43°C.
S (a) Mobile phases for the determination in the acidic range: 0.1 % aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile -the corresponding test results in Table 1 are labelled a).
(b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90%
acetonitrile - the corresponding test results in Table 1 are labelled b).
Calibration was carned out using unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known loge values (determination of the loge values by the retention times using linear interpolation between two successive alkanones).
The lambda max values were determined in the maxima of the chromatographic signals using the UV spectra from 200 nm to 400 nm.

Le A 32 986-Forei,~n Countries Starting materials of the formula (IV):
Example (IV-1) 15 g (50 mmol) of 81% pure 4-cyano-2-fluoro-5-ethylsulphonylamino-aniline (known from DE-A-4414568) in a mixture with 100 ml of acetic acid and 20 ml of conc. sulphuric acid are cooled to 5°C and admixed a little at a time with 12.7 g (100 mmol) of nitrosylsulphuric acid, and the mixture is stirred at from 5°C
to 10°C for 6 hours; a solution of 33.6 g (140 mmol) of tin(II) chloride dihydrate -dissolved in 15 ml of cone hydrochloric acid - is then added dropwise at 10°C. The mixture is stirred at 25°C for 12 hours, then stirred with ice-water and made alkaline using conc.
ammonia. The precipitated salt is filtered off with suction, the filtrate is made slightly acidic using conc. hydrochloric acid and extracted with ethyl acetate, and the extract is dried over sodium sulphate and concentrated using a rotary evaporator. The residue is recrystallized from isopropanol.
This gives 12.9 g (33% of theory) of 4-cyano-S-ethylsulphonylamino-2-fluoro-phenylhydrazine.
Example (IV-1) F
H2N~
'CN
~~CH3 Le A 32 986-Foreign Countries Step 1 H

9.2 g (0.4 mol) of sodium metal are dissolved in 200 ml of methanol, and the solution is admixed with 30.8 g (0.2 mol) of 2,5-difluoro-4-cyano-aniline. The stirring apparatus is fitted with a distillation head and heated to 90-95°C, and about 4/S of the amount of metanol is distilled off. After an extra stirring time of 30 minutes at 95°C, heating is removed, the content of the flask is admixed with water, cooled to 25°C
and adjusted to pH 5 using conc. hydrochloric acid, and precipitated product is filtered off with suction, washed with water and dried.
This gives 31.2 g (94% of theory) of 4-cyano-2-fluoro-S-methoxy-aniline of melting point 99°C, purity (method): 99% (HPLC, IogP 1.34).
1 S Step 2 - Variant a F
HzN~~ \
~CN
~~CH3 4.7 g (2.8 mmol) of 4-cyano-2-fluoro-S-methoxy-aniline are admixed with 100 ml of conc. hydrochloric acid and 30 ml of water, and the mixture is briefly heated to 40°C
and then cooled to 0°C. A solution of 2.6 g of sodium nitrite -dissolved in 30 ml of water - is then added dropwise, and the mixture is stirred at from 5°C
to 10°C for 60 minutes. The mixture is then filtered and the filtrate is, at 0°C, added dropwise to a solution of 18 g (8 mmol) of tin(II) chloride dihydrate in 100 ml of conc.

Le A 32 986-Foreign Countries hydrochloric acid. The suspension is then stirred at room temperature (20°C) for 60 minutes, made alkaline using 45% strength aqueous sodium hydroxide solution and extracted repeatedly with ethyl acetate. The organic phase is dried over sodium sulphate and concentrated under waterpump vacuum using a rotary evaporator.
This gives 3 g (60% of theory) of 4-cyano-2-fluoro-S-methoxy-phenylhydrazine of melting point 160°C.
Step 2 - Variant b F
H2N~
~CN
O\CH3 g (0.5 mol) of sodium metal are dissolved in 400 ml of methanol, and the solution is admixed with 68 g (0.4 mol) of 2,5-difluoro-4-cyano-phenylhydrazine. The stirnng apparatus is fitted with a distillation head and heated at from 80°C to 85°C, and about 80% of the methanol are distilled off. After an extra stirnng time of 3 hours at 15 85°C, heating is removed, the content of the flask is admixed with water, cooled to 25°C and neutralized using conc. hydrochloric acid, and precipitated product is filtered off with suction, washed with water and dried. For purification, the product is recrystallized from ethanol.
20 This gives 39 g (54% of theory) of 4-cyano-2-fluoro-5-methoxy-phenylhydrazine of melting point 163°C.

Le A 32 986-Forei;~n Countries _77_ Starting materials of the formula (VIII
Exampl~VII-1 ) O
30 g (370 mmol) of sodium acetate are initially charged in 200 ml of water.
With ice-cooling, 25 g (93 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone are added dropwise, and the mixture is stirred at room temperature (about 20°C) for 30 minutes. The reaction mixture is then admixed with 12 g (72 mmol) of 2,5-difluoro-4-cyano-phenylhydrazine and stirred at from 40°C to 50°C for 2 hours.
The cold precipitated product is filtered off with suction, washed with water and dried.
This gives 19 g (95.4% of theory) of 3,3,3-trifluoro-2-oxopropanal-1-(2,5-difluoro-4-cyano-phenylhydrazone) of melting point 181 °C.
1 S Example (VII-2) F
FsC w N~~ \
O
CN
O~CH3 7 g (87 mmol) of sodium acetate in 100 ml of water are admixed with 5.94 g (22 mmol) of 1,1-dibromo-3,3,3-trifluoro-acetone, and the mixture is stirred at room temperature (about 20°C) for 30 minutes, admixed with 3.0 g (17 mmol) of 4-cyano-2-fluoro-5-methoxy-phenylhydrazine and stirred at from 40°C to 50°C for 60 minutes and at 95°C for 10 minutes. After cooling to 20°C, the precipitated product is filtered off with suction, washed with water and dried.

Le A 32 986-Foreign Countries _78_ This gives 4.1 g (83% of theory) of 3,3,3-trifluoro-2-oxo-propanal-1-(4-cyano-fluoro-5-methoxy-phenylhydrazone) of melting point 168°C.
Example (VII-3) F
FsC w N~~ \
O / CN
,NH
HSCz S02 4.1 g (50 mmol) of sodium acetate in 50 ml of water are stirred at 80°C
with 3.6 g of 1,1-dibromo-3,3,3-trifluoro-acetone, the mixture is admixed at 25°C
with 2.58 g (10 mmol) of 4-cyano-5-ethylsulphonylamino-2-fluoro-phenylhydrazine, stirred at from 40°C to 50°C for 90 minutes and cooled to 10°C, and precipitated product is filtered off with suction, washed with water and dried.
This gives 3.03 g (83% of theory) of 3,3,3-trifluoro-2-oxopropanal-1-(4-cyano-ethylsulphonylamino-2-fluoro-phenylhydrazone) of melting point 127°C.
Example (VII-41 H
FsC ~NiN \
O ~ /
~CN
~NH
H5C2 SOz 4.1 g (50 mmol) of sodium acetate in SO ml of water are stirred at 80°C
with 3.6 g of 3,3-dibromo-1,1,1-trifluoro-2-butanone for 30 minutes, and the mixture is admixed at 25°C with 2.58 g (10 mmol) of 4-cyano-5-ethylsulphonylamino-2-fluoro-phenyl-Le A 32 986-Foreign Countries hydrazine, stirred at from 40°C to 50°C for 2 hours and cooled to 10°C. The precipitated product is filtered off with suction, washed with water and dried.
This gives 3.2 g (84.2% of theory) of 1,1,1-trifluoro-2-oxo-butanal-3-(4-cyano-ethylsulphonylamino-2-fluoro-phenylhydrazone) of melting point 211 °C.
Precursors of the formula I;XIV
Example (XIV-1~
CzHs O O
F
F3C-CF2 w ~~
~N
O
~CN
,NH

6.87 g (30 mmol) of 4-cyano-5-methylsulphonylamino-2-fluoro-aniline are initially charged in 100 ml of acetic acid, 4.7 g (34 mmol) of nitrosylsulphuric acid (92%
strength) are introduced a little at a time at 20°C with ice-cooling, and the mixture is stirred at 25°C for 2 hours. At 5-10°C, the mixture is subsequently added dropwise to a suspension of 10.6 g (45 mmol) of ethyl pentafluoropropinylacetate and 16.4 g (200 mmol) of sodium acetate in 200 ml of ethanol, the mixture is stirred at 25°C for 12 hours and stirred into water, and precipitated product is filtered off with suction, washed with water and dried. For purification, the product is recrystallized from isopropanol.
This gives 8.6 g (60.5% of theory) of 1-[(4-cyano-5-methylsulphonylamino-2-fluoro-phenyl)hydrazono]-4-ethoxycarbonyl-1,1,1,2,2-pentafluorobutan-3-one of melting point 165°C.

Le A 32 986-Foreign Countries Example (XIV-2) C2Hs O O
F
FZCIC ~N.~ \
O ~ ~ CN
,NH

S 10.7 g (47 mmol) of 4-cyano-5-methylsulphonylamino-2-fluoro-aniline are initially charged in 100 ml of acetic acid, 7.3 g (53 mmol) of nitrosylsulphuric acid (92%
strength) are introduced at 20°C a little at a time with ice-cooling, and the mixture is stirred at 25°C for 2 hours. At from 5°C to 10°C, the mixture is then added dropwise to a suspension of 14.2 g (71 mmol) of ethyl 1,1,1-difluorochloroacetoacetate and 26 g (313 mmol) of sodium acetate in 200 ml of ethanol, the mixture is stirred at 25°C
for 12 hours and stirred into water, and precipitated product is filtered off with suction, washed with water and dried.
This gives 13.7 g (66% of theory) of 1-[(4-cyano-S-methylsulphonylamino-2-fluoro-phenyl)hydrazono]-3-ethoxycarbonyl-1,1-difluoro-1-chloro-propan-2-one of melting point 175°C.

Le A 32 986-Foreign Countries Use Examples:
In the use examples, the following known compounds are used for comparison:

CI
(A) 2-(5-amino-2,4-dichloro-phenyl)-5-methyl-3(2H)-pyridazinone - known from WO 9639392.
H3C I ~ N CI
B N I \
O /
CI
N02 (B) 4-bromo-2-(2,4-dichloro-5-nitro-phenyl)-5-methyl-3(2H)-pyridazinone - known from WO 9639392.
H3C ( ~ N CI
Br N I \
O /
CI

(C) 2-(5-amino-2,4-dichloro-phenyl)-4-bromo-S-methyl-3(2H)-pyridazinone - known from WO 9639392.

Le A 32 986-Foreign Countries H3C ~ ~ N CI
N
O ~ /
~CI

(D) 2-(2,4-dichloro-5-nitro-phenyl)-5-methyl-3(2H)-pyridazinone - known from WO 9639392.

CN
(E) 2,5-difluoro-4-(4-methyl-6-oxo-1 (6H)-pyridazinyl)-benzonitrile - known from WO 9639392.

Le A 32 986-Foreign Countries Example A
Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound such that the particular amount of 1 S active compound desired is applied per unit area. The concentration of the spray liquor is chosen so that the particular amount of active compound desired is applied in 1000 litres of water per hectare.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0% - no effect (like untreated control) 100% - total destruction In this test, for example, the compounds of Preparation Example l, 2, 12, 13, 24, 40, 41, 46, 66, 84, 107, 112, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129 and show considerably stronger activity against weeds than the known compounds (A), (B), (C), (D) and (E).

Le A 32 986-Foreign Countries Example B
Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants of a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 10001 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0% - no effect (like untreated control) 100% - total destruction In this test, for example, the compounds of Preparation Example 1, 2, 12, 13, 24, 40, 41, 46, 66, 84, 107, 112, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129 and show considerably stronger activity against weeds than the known compounds (A), (B), (C), (D) and (E).

Le A 32 986-Foreign Countries Example C
Phaedon larvae test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with mustard beetle larvae (Phaedon cochleariae) while the leaves are still moist.
After the desired period of time, the kill in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.
In this test, for example, the compounds of Preparation Examples 1 and 2 show good activity.

Claims (14)

Claims
1. Substituted phenylpyridazinones of the general formula (I) in which R1 represents hydrogen, fluorine, chlorine or bromine, R2 represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy or alkylthio having in each case 1 or 2 carbon atoms, R3 represents the grouping -A1-A2-A3 in which A1 represents a single bond, represents oxygen, sulphur, -SO-, -SO2-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, A1 furthermore represents in each case optionally fluorine-, chlorine- or bromine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene, A2 represents a single bond, represents oxygen, sulphur, -SO-, -SO2-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, A2 furthermore represents in each case optionally fluorine-, chlorine-, bromine- or C1-C4-alkoxy-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene,#
A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, formyl, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, fluorine, chlorine, bromine, represents in each case optionally hydroxyl-, fluorine-, chlorine-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyloxy- or C1-C4-alkoxy-carbonyloxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or di-alkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally fluorine- or chlorine- substituted alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups, represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, C1-C4-alkyl- and/or C1-C4-alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylamino, cyclo-alkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-halogenoalkyl, C1-C4-alkyloxy, C1-C4-halogenoalkyloxy- and/or C1-C4-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C1-C4-alkyl, phenyl-C1-C4-alkoxy, phenyloxycarbonyl or phenyl-C1-C4-alkoxy-carbonyl, A3 furthermore represents in each case optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, dioxanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1-C4-alkyl, furyl-C1-C4-alkyl, thienyl-C1-C4-alkyl, oxazolyl-C1-C4-alkyl, isoxazole-C1-C4-alkyl, thiazole-C1-C4-alkyl, pyridinyl-C1-C4-alkyl, pyrimidinyl-C1-C4-alkyl, pyrazolylmethoxy, furyl-methoxy, represents perhydropyranylmethoxy or pyridyl-methoxy, R4 represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the alkyl groups, R5 represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the alkyl groups, and R6 represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the alkyl groups.
2. Substituted phenylpyridazinones according to Claim 1, characterized in that R1 represents hydrogen, fluorine or chlorine, R2 represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl, R3 represents the grouping -A1-A2-A3 in which A1 represents a single bond, represents oxygen, sulphur, -SO-, -SO2-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl or ethylsulphonyl, A1 furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl, A2 represents a single bond, represents oxygen, sulphur, -SO-, -SO2-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl or phenylsulphonyl, A2 furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl, A3 represents hydrogen, hydroxyl, amino, cyano, nitro, formyl, carboxyl, carbamoyl, sulpho, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl or dipropoxyphosphoryl, di-isopropoxyphosphoryl, represents in each case optionally fluorine- or chlorine-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxycarbonyl- or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo-propylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexylideneamino, cyclopentyloxycarbonyl, cyclohexyl-oxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexyl-methoxycarbonyl, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxy-carbonyl- and/or ethoxycarbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, A3 furthermore represents (in each case optionally fully or partially hydrogenated) dioxolanyl, dioxanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolemethyl, thiazolemethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, R4 represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl, R5 represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl, and R6 represents hydrogen, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl.
3. Substituted phenylpyridazinones according to Claim 1, characterized in that R1 represents hydrogen, fluorine or chlorine, R2 represents cyano or thiocarbamoyl, R3 represents the grouping -A1-A2-A3 in which A1 represents a single bond, represents oxygen, sulphur, -SO-, -SO2-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, methyl, ethyl, n- or i-propyl, methylsulphonyl or ethylsulphonyl, A1 furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl or propene-1,3-diyl, A2 represents a single bond, represents oxygen, sulphur, -SO-, -SO2-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propyl-sulphonyl or phenylsulphonyl, A2 furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl or propene-1,3-diyl, A3 represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulpho, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethyl-sulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethyl-sulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, represents in each case optionally fluorine- or chlorine-substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxycarbonyl- or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo-propylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexylideneamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentyl-methoxycarbonyl or cyclohexylmethoxycarbonyl, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl- and/or ethoxy-carbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl or benzyloxycarbonyl, A3 furthermore represents pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxa-diazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolemethyl, thiazolemethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, R4 represents hydrogen, cyano, thiocarbamoyl, nitro, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, R5 represents in each case fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, and R6 represents hydrogen, cyano, thiocarbamoyl, nitro, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl.
4. Substituted phenylpyridazinones according to any of Claims 1 to 3, characterized in that R1 represents fluorine.
5. Substituted phenylpyridazinones according to any of Claims 1 to 4, characterized in that R2 represents cyano.
6. Substituted phenylpyridazinones according to any of Claims 1 to 5, characterized in that R4 and R6 represent hydrogen or methyl.
7. Substituted phenylpyridazinones according to any of Claims 1 to 6, characterized in that R5 represents trifluoromethyl.
8. Substituted phenylpyridazinones according to any of Claims 1 to 7, characterized in that R3 represents A3.
9. Substituted phenylpyridazinones according to any of Claims 1 to 8, characterized in that A1 represents -NH- and A2 represents SO2.
10. Substituted phenylpyridazinones according to any of Claims 1 to 9, characterized in that A1 represents methylsulphonyl or ethylsulphonyl and A2 represents -CO-.
11. Process for preparing substituted phenylpyridazinones according to any of Claims 1 to 10, characterized in that (a) halogenoarenes of the general formula (II) in which R1, R2 and R3 are as defined in any of Claims 1 to 3 and X1 represents halogen are reacted with pyridazinones of the general formula (III) in which R4, R5 and R6 are as defined in any of Claims 1 to 3, or with acid adducts or alkali metal salts of compounds of the formula (III) if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or that (b) arylhydrazines of the general formula (IV) in which R1, R2 and R3 are as defined in any of Claims 1 to 3 are reacted with .beta.-trihalomethyl-enones of the general formula (V) in which R4, R5 and R6 are as defined in any of Claims 1 to 3 and X2 represents halogen, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or that (c) hydrazonecarboxylic acids of the general formula (VI) in which R1, R2, R3, R4, R5 and R6 are as defined in any of Claims 1 to 3 are condensed with ring-closure, i.e. reacted with a dehydrating agent, or that (d) 2,4-disubstituted phenylpyridazinones of the general formula (Ia) in which R1, R2, R4, R5 and R6 are as defined in any of Claims 1 to 3, are nitrated, i.e. reacted with a nitrating agent, or that (e) hydrazonecarbonyl compounds of the general formula (VII) in which R1, R2, R3, R5 and R6 are as defined in any of Claims 1 to 3 are reacted with alkoxycarbonylmethylenephosphoranes of the general formula (VIII) in which R4 is as defined in any of Claims 1 to 3 and R represents alkyl having 1 to 6 carbon atoms, or with trialkyl phosphonocarboxylates of the general formula (IX) in which R4 is as defined in any of Claims 1 to 3 and R represents alkyl having 1 to 6 carbon atoms, in each case optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.
12. Hydrazonecarbonyl compounds of the general formula (VIIa) in which R1 represents fluorine, chlorine or bromine, R2-1 represents cyano, carbamoyl, thiocarbamoyl, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy or alkyl-thio having in each case 1 or 2 carbon atoms, R3 represents the grouping -A1-A2-A3, in which A1 represents a single bond, represents oxygen, sulphur, -SO-, -SO2-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, A1 furthermore represents in each case optionally fluorine-, chlorine- or bromine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene, A2 represents a single bond, represents oxygen, sulphur, -SO-, -SO2-, -CO- or the grouping -N-A4-, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl, A2 furthermore represents in each case optionally fluorine-, chlorine- or bromine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene, A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thio-cyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkyl-sulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or di-alkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally fluorine- or chlorine-substituted alkenyl, alkenyloxy, alkenyl-amino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyl-oxy, alkinylamino or alkinyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups, represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, C1-C4-alkyl- and/or C1-C4-alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cyclo-alkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkyloxy-, C1-C4-halogenoalkyloxy- and/or C1-C4-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C1-C4-alkyl, phenyl-C1-C4-alkoxy, phenyloxycarbonyl or phenyl-C1-C4-alkoxycarbonyl, A3 furthermore represents in each case optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1-C4-alkyl, furyl-C1-C4-alkyl, thienyl-C1-C4-alkyl, oxazolyl-C1-C4-alkyl, isoxazole-C1-C4-alkyl, thiazole-C1-C4-alkyl, pyridinyl-C1-C4-alkyl, pyrimidinyl-C1-C4-alkyl, pyrazolylmethoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy, R5 represents hydrogen, cyano, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy, alkyl-thio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, and R6 represents hydrogen, cyano, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted alkyl, alkoxy, alkyl-thio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups.
13. Crop protection compositions, characterized in that they comprise at least one substituted phenylpyridazinone according to any of Claims 1 to 10 and customary extenders and/or surfactants.
14. Method for controlling undesirable plants or animal pests, in particular insects, characterized in that at least one substituted phenylpyridazinone according to any of Claims 1 to 10 is allowed to act on undesirable plants or animal pests and/or their habitat.
CA002327806A 1998-04-09 1999-03-26 Substituted phenyl pyridazinones Abandoned CA2327806A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19815947 1998-04-09
DE19815947.1 1998-12-23
DE19859685 1998-12-23
DE19859685.5 1998-12-23
PCT/EP1999/002086 WO1999052878A1 (en) 1998-04-09 1999-03-26 Substituted phenyl pyridazinones

Publications (1)

Publication Number Publication Date
CA2327806A1 true CA2327806A1 (en) 1999-10-21

Family

ID=26045387

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002327806A Abandoned CA2327806A1 (en) 1998-04-09 1999-03-26 Substituted phenyl pyridazinones

Country Status (8)

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

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6121201A (en) 1998-09-11 2000-09-19 Ishihara Sangyo Kaisha, Ltd. Diaryl ethers and processes for their preparation and herbicidal and desiccant compositions containing them
JP3890816B2 (en) * 1998-12-09 2007-03-07 住友化学株式会社 Method for producing pyridazin-3-one derivative
AU2001256287A1 (en) * 2000-04-14 2001-10-30 Basf Aktiengesellschaft 2-phenyl-2h-pyridazine-3-ones
AU2001262197A1 (en) * 2000-04-14 2001-10-30 Basf Aktiengesellschaft 2-phenyl-2h-pyridazine-3-ones
DE10034803A1 (en) * 2000-07-18 2002-01-31 Bayer Ag Substituted sulfonic acid anilides
EP1613607B1 (en) 2003-04-08 2013-01-09 Basf Se Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds
CN101041639B (en) * 2005-03-17 2010-05-26 南开大学 4-Substituted phenylpyridazines and their herbicidal activity
SI1928454T1 (en) 2005-05-10 2015-01-30 Intermune, Inc. Pyridone derivatives for modulating stress-activated protein kinase system
WO2009149188A1 (en) 2008-06-03 2009-12-10 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
JP5842594B2 (en) * 2010-12-27 2016-01-13 住友化学株式会社 Pyridazinone compounds, herbicides containing them, and harmful arthropod control agents
GB201121317D0 (en) * 2011-12-09 2012-01-25 Syngenta Ltd Herbicidal compounds
MX2015000830A (en) 2012-07-18 2015-10-26 Sunshine Lake Pharma Co Ltd Nitrogenous heterocyclic derivatives and their application in drugs.
CN103664795B (en) * 2012-09-06 2017-10-03 华东理工大学 Pyridazinone compound and application thereof
AR092742A1 (en) 2012-10-02 2015-04-29 Intermune Inc ANTIFIBROTIC PYRIDINONES
MX2016012808A (en) 2014-04-02 2017-01-05 Intermune Inc Anti-fibrotic pyridinones.
WO2017178582A1 (en) * 2016-04-15 2017-10-19 Syngenta Participations Ag Herbicidal pyridazinone compounds
GB201717080D0 (en) 2017-10-18 2017-11-29 Syngenta Participations Ag Chemical process

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH373919A (en) * 1959-02-02 1963-12-15 Ciba Geigy Method of controlling weeds
DE2808193A1 (en) * 1978-02-25 1979-09-06 Basf Ag PYRIDAZONE CONNECTIONS
DE19520613A1 (en) * 1995-06-06 1996-12-12 Bayer Ag Phenylpyridazinones
ATE383344T1 (en) * 1995-08-21 2008-01-15 Sumitomo Chemical Co PYRIDAZINE-3-ONE DERIVATIVES, THEIR USE AND INTERMEDIATE PRODUCTS FOR THEIR PRODUCTION
ZA978995B (en) * 1996-10-21 1998-08-25 Sumitomo Chemical Co Production of pyridazine herbicide
AR009380A1 (en) * 1996-10-21 2000-04-12 Sumitomo Chemical Co PROCESS OF PREPARATION OF A DERIVATIVE OF PIRIDAZIN-3-ONA, USEFUL AS A HERBICIDE, CARBOXYLIC ACID FOR USE THEREOF, SALE OF THIS LAST AND PROCESS TO PREPARE SUCH CARBOXYLIC ACID
DE19754348A1 (en) * 1996-12-11 1998-06-18 Ciba Geigy Ag New 2-(hetero)aryl-2(3H)-pyridazinone derivatives
IL123339A0 (en) * 1997-02-19 1998-09-24 Sumitomo Chemical Co Pyridazin-3-one derivatives and their use
IL123340A0 (en) * 1997-02-20 1998-09-24 Sumitomo Chemical Co Pyridazin-3-one derivatives and their use

Also Published As

Publication number Publication date
WO1999052878A1 (en) 1999-10-21
CN1305466A (en) 2001-07-25
KR20010042411A (en) 2001-05-25
AU3702599A (en) 1999-11-01
AU742108B2 (en) 2001-12-20
EP1070055A1 (en) 2001-01-24
BR9909548A (en) 2000-12-12
JP2002511452A (en) 2002-04-16

Similar Documents

Publication Publication Date Title
CA2223094C (en) Phenylpyridazinones
AU2001262271B2 (en) Substituted iminoazines used as herbicides
AU742108B2 (en) Substituted phenyl pyridazinones
JP2002521373A (en) Substituted benzoylcyclohexanediones
AU764182B2 (en) Substituted benzoyl ketones, methods for producing them and their use as herbicides
AU3157601A (en) Substituted benzoylcyclohexane diones for use as herbicides
MXPA02006966A (en) Substituted aryl ketones.
US6559102B1 (en) Substituted 3-aryl-pyrazoles
JP2002506062A (en) 6-Substituted 2,4-diamino-1,3,5-triazine derivatives having at least two asymmetrically substituted carbon atoms, their preparation and their use as herbicides
AU764272B2 (en) Substituted 1,3,5-triazines
AU716093B2 (en) Substituted 1-(3-pyrazolyl)-pyrazoles having herbicidal activity and intermediates for their preparation
CA2373665C (en) Substituted thienocycloalk(en)ylamino-1,3,5-triazine
CA2256508A1 (en) 3-cyanoaryl pyrazoles and use thereof as herbicides
US6610631B1 (en) Substituted aryl ketones
US6992044B1 (en) Substituted phenyluracils
CA2251783A1 (en) 3-cyanoaryl pyrazoles and their use as herbicides
AU765922B2 (en) Substituted N-cyano amidines
AU5401700A (en) Substituted herbicidal phenyluracils
CA2319053A1 (en) Substituted heteroarylmethyl compounds used as herbicides
JP2001525401A (en) Substituted 2,4-diamino-1,3,5-triazines
MXPA00009826A (en) Substituted phenyl pyridazinones
CA2332443A1 (en) Substituted 1,3-diaza-2-(thi)oxo-cycloalkanes
CA2272657A1 (en) Phenyl-uracil derivatives with herbicide effect
MXPA99004750A (en) Phenyl-uracil derivatives with herbicide effect
MXPA00005585A (en) Substituted 2,4-diamino-1,3,5-triazines

Legal Events

Date Code Title Description
FZDE Dead