MXPA00009826A

MXPA00009826A - Substituted phenyl pyridazinones

Info

Publication number: MXPA00009826A
Application number: MXPA/A/2000/009826A
Authority: MX
Inventors: Hupperts Achim; Christoph Erdelen; Dollinger Markus; Ingo Wetcholowsky; Markwilhelm Drewes; Karlheinz Linker
Original assignee: Bayer Aktiengesellschaft; Dollinger Markus; Drewes Mark Wilhelm; Christoph Erdelen; Hupperts Achim; Karlheinz Linker; Ingo Wetcholowsky
Priority date: 1998-04-09
Filing date: 2000-10-06
Publication date: 2001-07-31

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

SUBSTITUTE FENILPIRIDAZINQNAS. Field of the invention. The invention relates to novel substituted phenylpyridazinones, to processes for their preparation and to their use as agents for the treatment of plants, especially as herbicides and as insecticides. Description of the prior art. It is already known that certain substituted phenylpyridazinones have herbicidal properties (see DE-A-1105232, DE-A-1670309, DE-A-1670315, DE-A-1695840, DE-A-25266643, DE-A-2706700, DE -A-2808193, DE-A-2821809, DE-A-19754348, US-A-5298502, WO-A-96/39392, OA-97/07104). However, the herbicidal activity of these compounds is not satisfactory from all points of view. Detailed description of the invention. New substituted phenylpyridazinones of the general formula (I) have now been found, in which 1 denotes hydrogen, fluorine, chlorine or bromine, R2 means cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or means alkyl, alkoxy or alkylthio with respectively 1 or 2 carbon atoms substituted, respectively, by fluorine and / or by chlorine , R3 means the grouping -A'-A2-A3, in which A1 means a single bond, means oxygen, sulfur, -SO-, -SO2-, -CO- or means the grouping -N-A4-, where A4 means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkenyl with 3 to 4 carbon atoms, alkynyl with 3 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl, alkylsulfonyl with 1 to 4 carbon atoms carbon or phenylsulfonyl, A1 also means alkanediyl with 1 to 6 carbon atoms, alkenediyl with 2 to 6 carbon atoms, azaalkenediyl with 2 to 6 carbon atoms, alkynediyl with 2 to 6 carbon atoms, cycloalkanediyl with 3 to 6 carbon atoms, cycloalkenodiyl with 3 to 6 carbon atoms or phenylene, respectively substituted by fluorine, chlorine or bromine, A2 means a single bond, means oxygen, sulfur, -SO-, -SO2-, -CO- or means the group -N-A4-, where A4 means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl, alkylsulfonyl with 1 to 4 carbon atoms or phenylsulfonyl, A2 also means alkanediyl having 1 to 3 carbon atoms, alkenediyl with 2 to 6 carbon atoms, azaalkenediyl with 2 to 6 carbon atoms, alkynediyl with 2 to 6 carbon atoms, cycloalkanediyl with 3 to 6 carbon atoms, cycloalkenodiyl with 3 to 6 carbon atoms or phenylene optionally substituted by fluorine, chlorine, bromine or alkoxy with 1 to 4 carbon atoms, respectively, means hydrogen, hydroxy, amino, cyano, isocyano, thiocyanate, nitro, formyl, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl , fluorine, chlorine, bromine, means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or dialkoxy (thio) phosphoryl with, respectively, 1 to 6 carbon atoms in the alkyl groups, respectively substituted optionally by hydroxy, by fluorine, by chlorine, by alkoxy with 1 to 4 carbon atoms, by alkyl-carbonyloxy with 1 to 4 carbon atoms or by alkoxy-carbonyloxy with 1 to 4 carbon atoms, means alkenyl, alkenyloxy , alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl with, respectively, 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl, respectively substituted, if appropriate, by fluorine or chlorine, means cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, with, respectively, 3 to 6 carbon atoms in the cycloalkyl groups and, optionally, 1 to 4 carbon atoms in the alkyl groups, optionally substituted by fluorine, chlorine, cyano, carboxy, alkyl with 1 to 4 carbon atoms and / or alkoxycarbonyl with 1 to 4 carbon atoms. at 4 carbon atoms, or means phenyl, phenyloxy, phenyl-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkoxy, phenyloxycarbonyl or phenyl-alkoxycarbonyl with 1 to 4 carbon atoms substituted respectively by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by halogen with 1 to 4 carbon atoms, by alkyloxy with 1 to 4 carbon atoms of carbon, by haloalkoxy with 1 to 4 carbon atoms and / or by alkoxycarbonyl with 1 to 4 carbon atoms, A3 further means pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, dioxanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-alkyl with 1 to 4 carbon atoms, furyl-alkyl with 1 to 4 carbon atoms, thienyl-alkyl with 1 to 4 carbon atoms, oxazolyl - alkyl with 1 to 4 carbon atoms, isoxazole-alkyl with 1 to 4 carbon atoms, thiazole-alkyl with 1 to 4 carbon atoms, pyridinyl-alkyl with 1 to 4 carbon atoms, pyrimidinyl-alkyl with 1 to 4 atoms carbon, pyrazolylmethoxy, furilme toxi respectively, wholly or partially hydrogenated, means perhydropyranylmethoxy or pyridylmethoxy, R4 means hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl with, respectively, 1 to 4 carbon atoms in alkyl groups, respectively substituted, if appropriate, by fluorine and / or by chlorine, R5 means hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means alkyl, alkoxy, alkylthio , alkylamino, dialkylamino or alkoxycarbonyl having, respectively, 1 to 4 carbon atoms, in the alkyl groups substituted respectively by fluorine and / or by chlorine, and R6 signifies hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means alkyl, alkoxy, alkylthio, alkylamino, dialkylammo or alkoxycarbonyl with, respectively 1 to 4 carbon atoms in the alkyl groups respectively substituted, if appropriate, by fluorine and / or by chlorine The novel substituted femipipdazinones of the general formula (I) exhibit intrinsic biological properties, are characterized in particular by a potent herbicidal and insecticidal activity. definitions the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl, are respectively straight-chain or branched chain In general halogen means fluorine, chlorine, bromine or iodine, preferably means fluorine, chlorine or bromine, especially means fluorine or chlorine Preferably, R.sub.1 is hydrogen, fluorine or chlorine, preferably R.sub.2 is cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or trifluoromethyl, preferably R.sub.3 is the group -A'-A2-A \ in which A1 denotes a single bond , means oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -N-A4-, where A4 means hydrogen , hydroxy, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl, A1 also means methylene, ethane-1,1-dnon, ethane-1, 2-dnon, propane-1,1-dnon, propane-1, 2-dnon, propane-1, 3-dulo, ethene-1,2 -dnlo, propene-1,2- dnlo, propene-l, 3-dnlo, ethmo-l, 2-dnlo, propino-1,2-dulo or prop? no-1,3-dnlo, A2 means a single bond , means oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -N-A4-, where A "means hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n - or γ-propoxy, methylsulfomyl, ethylsulfomyl, n- or ω-propylsulphyl or femlsulphonyl, A2 also means methylene, ethane-1, l-d-halo, ethane-1, 2-dnon, propane-1,1-dulo, propane- 1,2-dnl, propane-l, 3-dulo, etheno-l, 2-dnlo, propene-1,2-dulo, propene-l, 3-dnlo, ethmo-l, 2-dulo, propmo-l, 2-dulo or prop? No-1,3-dnlo, A3 means hydrogen, hydroxy, amino, cyano, nitro, formyl, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, means methyl, ethyl, n- or 1- propyl, n-, 1-, s- or t-butyl, n-, 1-, s- or t-pentyl, methoxy, ethoxy, n- or 1-propoxy, n-, 1-, s- or t-butoxy, n-, 1-, s- or t-pentyloxy , menino, ethylthio, n- or 1-propylthio, n-, 1-, s- or t-butylthio, methylsulfiyl, ethylsulfimyl, n- or 1-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or β-propyl sulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, 1-, s- or t-butylamino, dimethylammon, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphospho- ne, diethoxyphosphoyl or dipropoxyphospho- ne, dnsopropoxyphospho-substituted respectively if appropriate by fluorine, chlorine, methoxy or ethoxy, means ethenyl, propene, butemyl, propenyloxy, butenyloxy, propenylamino, butemlam or, propihdenamino, butihdenammo, prope loxicarbomlo, buteniloxicarbomlo, enrulo, propimlo, butmilo, propimloxi, butimloxi, propynylamino, butynylamino, propimloxicarbomlo or but iloxicarbomlo substituted in each case optionally fluorine or chlorine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentyldename, cyclohexyhdenammo, cyclopentyloxycarbonyl, cyclohexyloxycarbomyl, cyclopentylmethoxycarbonyl or cyclohexdmethoxycarbomyl respectively substituted, where appropriate, by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, by metoxicarbomlo or etoxicarbonüo, or means femlo, femloxi, benzyl, femletilo, benzyloxy, femloxicarbonilo, benzyloxycarbonyl substituted respectively optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine , by methyl, by ethyl, by n- or i propyl, by trifluoromethyl, by methoxy, by ethoxy, by n or i propoxy, by difluoromethoxy, by trifluoromethoxy, by methoxycarbonyl and / or by ethoxycarbom, A3 also means dioxolamlo, dioxamlo, pyrrolyl, pyrazole, tmidazolyl, tpazoluo, fuplo, thienyl, oxazole, isoxazolyl, thiazolium, isothiazoium, oxadiazole, thiadiazole, pipdmil, pyrimidinyl, tpazinyl, pyrazoluthime, mplmethyl, tiemlmethyl, oxazohlmeno, isoxazolmethyl, thiazolmethyl, pipimelimide. , pyrundinylmethyl, pyrazolemethoxy, fuplmethoxy or pipdilmethoxy (each case wholly or partly hydrogenated), preferably R4 means hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means methyl, ethyl, n- or? -propyl, n- i-, s- or t-butyl, methoxy, ethoxy, menino, ethylthio, methylamino, ethylamino , dimethylamino, metoxicarbomlo or etoxicarbomlo substituted in each case optionally fluorine- and / or chlorine, preferably, R5 is hydrogen, carboxy, cyano, carbamoyl, nocarbamoilo, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or represents methyl , ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, menino, etilno, methylamino, ethylamino, dunetilamino, metoxicarbomlo or etoxicarbomlo, substituted in each case optionally fluorine- and / or by chloro, preferably, R6 means hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means methyl, ethyl, n- or i-propyl, n-, i- , substituted s- or t-butyl, methoxy, ethoxy, menino, ethylthio, methylamino, ethylamino, dimethylamm, methoxycarbom or ethoxycarbomide respectively or given by fluorine and / or chlorine R 1 is particularly preferably hydrogen, fluorine or chlorine, particularly preferably R 2 is cyano or thiocarbamoyl, and R 3 is particularly preferred when the crush is -A'-A2-A3 where A 'means a simple bond, means oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -N-A4-, where A4 means hydrogen, methyl, ethyl, n- or 1- propyl, methylsulfonyl or ethylsulfonyl, A1 further means methyl, ethane-1,1-diyl, ethane-1, 2-diyl, propane-1,1-diyl, propene-1, 2-diyl, propane-1, 3-diyl , ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl, A2 means a single bond, means oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -N-A4-, where A4 is hydrogen, methyl, ethyl, n- or i- propyl, methoxy, ethoxy, n- or i-propoxy, metiisulfonilo, ethylsulfonyl, n- or i- propylsulfonyl or phenylsulfonyl, A 2 represents methylene further , ethane-l, l-diyl, ethane-l, 2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-l, 3-diyl, ethene-l, 2-diyl, propene -1,2- diyl or propene- 1,3-diyl, A3 means hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, means 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, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl , ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i- propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted respectively optionally fluorine, chlorine, methoxy or ethoxy, means propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butin-loxycarbonyl, respectively substituted by fluorine or chlorine, respectively, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, ciclohexihdenamino, ciclopentiloxicarbomlo, ciclohexiloxicarbomlo, ciclopentilmetoxicarbonilo or ciclohexilmetoxicarbomlo substituted respectively optionally fluorine- by chlorine, by cyano, by carboxy, by methyl, by ethyl, by n- or l-propyl, by methoxycarbom or by ethoxycarbonyl, or by fem- lo, phenyloxy, benzyl, phenylethyl, benzyloxy, femloxycarbomyl or benzyloxycarbom- or substituted, respectively, if appropriate by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- or l-propyl, by tpflúormethyl, by methoxy, by ethoxy, by n- oi propoxy, by difluoromethoxy, by tpflúormetoxi, by methoxycarbonyl and / or by ethoxycarbonyl, A3 also means pirazohlo, ímidazohlo, tpazohlo, fuplo, I tend, oxazo it, isoxazolyl, tiazohlo, isotiazohlo, oxadiazohlo, tiadiazohlo, pipdimlo, pirurudinilo, tpazimlo, pirazohlmetilo, fuplmetilo, tiemlmetilo, oxazohlmetilo, isoxazolylmethyl, tiazolmetilo, piridimhnetilo, pirnnidinilmetilo, pirazolilmetoxi, fuplmetoxi or pipdilmetoxi R 4 is particularly preferably hydrogen, cyano, thiocarbamoyl, nitro, fluorine, chlorine, bromine or methyl, ethyl, n- or β-propyl, methoxy, ethoxy, menino, ethyl, methylamino, ethylamino or dimethylamino respectively substituted, if appropriate, by fluorine and / or chlorine, particularly preferably R 5 is methyl, ethyl, n- or 1-propyl substituted respectively by fluorine and / or chlorine, particularly preferably R 6 is hydrogen, cyano, thiocarbamoyl, nitro, fluorine, chlorine, bromine or methyl, ethyl, n - or 1-propyl, methoxy, ethoxy, menino, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbomyl or ethoxycarbonyl respectively substituted, where appropriate, by fluorine and / or by chlorine The definitions of the radicals given above in general or indicated in the ranges preferred are valid both for the final products of the formula (I) and also, correspondingly, for the starting products or for the intermediate products necessary respectively for the preparation. These definitions can be combined arbitrarily with each other, ie even between the Preferred ranges indicated According to the invention, preferred are the compounds of the formula (I), in which a combination of the The preferred compounds according to the invention are particularly preferred compounds of the formula (I), in which a combination of the meanings indicated above is especially preferred. The compounds of the formula (I) which are very particularly preferred have been the following groups Group 1.

In this case Ar has, by way of example, the meanings indicated 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-difluo-cyano-phenyl, 2-chloro-4-cyano-5-methyl- phenyl, 2-fluoro-4-cyano-5-methyl-phenyl, 2-chloro-4-cyano-5-trifluoromethyl-phenyl, 2-fluoro-4-cyano-5-trifluoromethyl-phenyl, 2,5-difluoro- 4-thiocarbamoyl-phenyl, 2-fluoro-4-cyano-5-methoxy-phenyl, 2-fluoro-4-cyano-5-i-propoxy-phenyl, 2-chloro-4-cyano-5- (2-propynyloxy) ) -phenyl, 2-fluoro-4-cyano-5- (1-methyl-2-propynyloxy) -phenyl, 2-chloro-4-thiocarbamoyl-5-i-propoxy-phenyl, 2-fluoro-4-cyano- 5- (2-propenyloxy) -phenyl, 2-chloro-4-cyano-5-methylsulphonylamino-phenyl, 2-fluoro-4-cyano-5-ethylsulfonylamino-phenyl, 2-fluoro-4-thiocarbamoyl-5 methyl-sulfonylamino-phenyl, 2-chloro-4-cyano-5-ethyl sulfonium lamino-phenyl, 2-fluoro-4-cyano-5-cyclopropylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-i-propylsulfonylamino-phenyl, 2-chloro-thiocarbamoyl-5-ethylsulfonylamino-phenyl, 2-chloro-4-cyano-5-cyanoamino-phenyl, 2-fluoro-4- cyano-5-trifluoromethylsulfonylamino-phenyl, 2-fluoro-4-cyano-5- (2,2-difluoromethylsulfonylamino) -phenyl, 2-fluoro-4-cyano-5-phenylsulfonylamino-phenyl, 2-fluoro-4-cyano 5-t-Butylsulfonylamino-phenyl, 2-chloro-4-cyano-5-methoxycarbonyl-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonyl-phenyl, 2-fluoro-4-thiocarbamoyl-5-methoxycarbonyl- ^ a- = a ^ - »^ afe- femlo, 2-fluoro-4-c? ano-5- (l-met? l-2-prop? n? lt? o) -fen? lo, 2-fluoro-4-c? ano-5-methylamino- phenyl, 2-chloro-4-t? ocarbamo? l-5-methox? carbomlmet? l-phenol, 2-chloro-4-c? ano-5- (N-met? l-et? lsulfon? lam ? no) -femlo, 2-chloro-4-c? ano-5 -? - propox? carboml-fe lo, 2-fluoro-4-c? ano-5- (b? s-et? lsulfon? l- am? no) -femlo, 2-fluor-4-c? ano-5- (N-met? lsulfon? l N-enlsulfon? lam? no) -phenol, 2-fluoro-4-c? ano-5 - (l-methox? carbon? l-ethoxy?) - femlo, 2-fluoro-4-c? ano-5-c? cloprop? lox? -femlo, 2-chloro-4-c? ano-5-dunethylamino -Form, 2-fluorine-4-cyano-5-tetrahydroform? lomethox? -phemyl, 2-fluorine-4-c? ano-5-am? no-femlo, 2-fluoro-4-c? ano-5-methylaminocarbon-phenol, 2-fluoro-4-c-ano-5-methylsulfomloxy-femlo, 2-chloro-4-c? ano-5-d? fiúormetox? -fen? lo , 2-fluoro-4-c? Ano-5-ethoxycarbomlmethoxy-femlo, 2-fluoro-4-c? Ano-5-d? Met? Lam? Nocarboml-phenol, 2-fluoro-4-c? An -5-c? Anometox? -femlo, 2-fluoro-4-c? Ano-5- (2-chloro-2-propemlox?) - phenol, 2-fluoro-4-c? Ano-5-h Drox? -femlo, 2-fluoro-4-c? ano-5-mtro-phenol, 2-fluoro-4-c? ano-5-diethoxyphospholamino-femlo, 2-fluoro-4-c? a no-5-chlorosulfoml-phenol, 2-fluoro-4-c-ano-5-form? lam? no-phenol, 2-chloro-4-c? an-5-ethoxy? carbon? lox? -femlo, 2-fluoro-4-c? ano-5-diethoxyphospho-methoxy-femlo, 2-chloro-4-c? ano-5-hydrox? -femlo, 2-fluoro-4-c? ano-5- (N, Nd? Acet? L-am? No) -femlo, 2-fluoro-4-c? Ano-5-acet? Lam? No-femlo, 2-chloro-4-c? Ano-5-noc? anato-phenol, 2-fluoro-4-c? ano-5-d? et? lam? noox? -femlo, 2-fluoro-4-c? ano-5-tetrahydrofuryloxy-phenyl, 2-fluoro-4 -c? ano-5-ure? do-fen? lo, 2-fluoro-4-c? ano-5-dunetoxymethylene-phenyl, 2-chloro-4-c? ano-5-ethox? met? lam? no -femlo, 2-fluoro-4-c? ano-5- (2-chloro-ethox? carbomlox?) - femlo, 2-chloro-4-c? ano-5-d? met? lam? nomet? ammo-femlo, 2-chloro-4-c-ano-5- (perh.drop? ran-4? lox?) - phenol, 2-fluoro-4-c? ano-5- (2-methox) carbon? l-enl) -phenol, 2-chloro-4-cyano-5- (2-carboxy-2-chloro-et? l) -phenol, 2-fluoro-4-c ? ano-5- (2-chloro-2-methox? carboml-et? l) -fen? lo, 2-fluoro-4-c? ano-5- (2-chloro-2-s-butox? carbon? l) -phemyl, 2-fluoro-4-c? ano-5- (2-chloro-2-carbamo? l-et? l) -phenol, 2-fluoro-4-c? ano-5- ( 2-chloro-2-methox? Carbonu-l-met? Let? L) -fen 2-fluorine-4-cyano-5- (1, 2- d? bromo-2-methox? carbon? l-et? l) -phenol, 2-chloro-4-c? ano-5- (2-chloro-2-? -propox? -carboml-et? l ) -phemyl, 2-fluoro-4-cyano-5- (2-carboxy-2-chloro-et? l) -phemyl, 2-fluoro-4-cyano-5- (2-chloro- 2-et? Lam? Nocarbon? Let? L) -femlo, 2-fluoro-4-c? Ano-5- (2-al? Lam? Nocar-bon? L-2-chloro-et? L) -fen It, 2-fluorine-4-cyano-5- (2-ethoxy-carboml-ethene) -phenol, 2-fluoro-4-cyano-5- (2-chloro-2-) c? cloprop? lam? nocarboml-et? l) -femlo, 2-fluoro-4-c? ano-5- (2-chloro-2-dunet? lam? nocarbon? l-et? l) -femlo, 2 -chloro-4-cyano-5- (2-chloro-2-et? lsulfon? l-am? nocarboml-et? l) -phemyl, 2-fluoro-4-t? ocarbamo? l-5- ( 2-et? Lam? Nocarboml-eten? L) -femlo, 2-fluoro-4-c? Ano-5- (l-ethox? Carboml-et? L) -femlo, 2-chloro-4-c? An -5- (l-etox? Car-bomlet? L) -phenol, 2-chloro-4-c? Ano-5-carbox? -femlo, 2-fluoro-4-c? Ano-5 -? - butox? -femlo, 2-chloro-4-c? ano-5-? -butox? -fen? lo, 2-chloro-4-c? ano-5- (2-methox? -etho?) -phen? lo, 2-fluoro-4-c? ano-5- (N-acet? lN-met? l sulfoml-am? no) -fen? lo, 2-fluoro-4-c? ano-5- (N-prop) ? on? lN-methersulfon? l-am? no) -fen? lo, 2-fl uor-4-c? ano-5- (N -? - but-ro? lN-met? lsulfoml-am? - no) -phenol, 2-fluoro-4-cyano-5- (Np? valo? lN-met? lsulfoml-am? no) -phenol, 2-fluoro-4-c? ano-5 - (N-benzoyl-N-methylsulfomylamino) -phenyl, 2-fluoro-4-cyano-5- (N- (4-methoxy? -benzoyl) - (N- methylsulfonyl-amine) -phenol, 2-fluoro-4-cyano-5- (N-acetyl-N-ethylsulfomyl-amine) -phenol, 2-fluorine -4-c? Ano-5- (N-prop? Oml-N-et? Lsulfoml-am? No) -femlo, 2-fluoro-4-c? Ano-5- (N -? - but? Ro? lN-et? lsulfon? l-am? no) -femlo, 2-fluoro-4-c? ano-5- (Np? valo? lN-et? lsulfoml-am? no) -femlo, 2-fluoro-4 -c-ano-5- (N-benzo-lN-et? lsulfoml-am? no) -femlo, 2-fluoro-4-c? ano-5- (N- (4-methox? -benzo? l) -N-et? Lsulfoml-a? Runo) -femlo, 2-fluoro-4-t? Ocarbamo? L-5- (N-acet? LN-met? Lsulfomlam? No) -femlo, 2-fluoro-4- Uocarba-mo-l-5- (N-prop? Oml-N-met? Lsulfoml-am? No) -femlo, 2-fluoro-4-t? Ocarbamo? L-5- (N -? - but? Ro ? N-methylsulfomyl-amino) -phemyl, 2-fluoro-4-t? ocarbamo? l-5- (Np? valo? N-me-t? lsulfoml-am? no) -femlo, 2- fluorine-4-t? ocarbamo? l-5- (N-benzo? N-met? l sulfoml-am? -no) -phemyl, 2-fluoro-4 t? ocarbamo? l-5- (N- (4- methox? -benzo? l) -N-met? lsulfoml-ammo) -femlo, 2-fluoro-4-t? ocar bamo? l-5- (N-acet? l-N-et? lsulfon? l-ammo) -phenol, 2-fluoro-4- thiocarbamoyl-5- (N-propionyl-N-ethylsulfonyl-amino) -phenyl, 2-fluoro-4-thiocarbamoyl-5- (Ni-butyroyl-N-ethylsulfonyl-amino) -phenyl, 2-fluoro-4-thiocarbamoyl- 5- (N-pivaloyl-N-ethylsulfonyl-amino) -phenyl, 2-fluoro-4-thiocarbamoyl-5- (N-benzoyl-N-ethylsulfonyl-amine) -phenyl, 2-fluoro-4-thiocarbamoyl- 5- (N- (4-methoxy-benzoyl) -N-ethylsulfonyl-amino) -phene-nyl. Group 2.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 3.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 4.

- - In this case Ar has, by way of example, the meanings indicated in group 1. Group 5.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 6.

In this case Ar nene, in an exemplary way, the meanings indicated in group 1. Group 7.

In this case Ar has, by way of example, the meanings indicated . ^^ kg ^^ in group 1. Group 8.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 9.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 10.

In this case Ar has, by way of example, the meanings indicated in group 1.

Group 11 In this case Ar has, by way of example, the meanings indicated in group 1. Group 12.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 13.

In this case Ar has, by way of example, the meanings indicated in group 1.

- - Group 14.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 15.

In this case Ar nene, in an exemplary manner, the meanings indicated in group 1. Group 16.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 17.

- - In this case Ar has, by way of example, the meanings indicated in group 1. Group 18. CF. Ar ~ // - ^ (IA-18) OR In this case Ar has, by way of example, the meanings indicated in group 1. Group 19.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 20.

In this case Ar has, by way of example, the meanings indicated in group 1.

Group 21 In this case Ar has, by way of example, the meanings indicated in group 1. Group 22.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 23.

In this case Ar has, by way of example, the meanings indicated in group 1.

Group 24 In this case Ar has, by way of example, the meanings indicated in group 1. Group 25.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 26.

In this case Ar has, by way of example, the meanings indicated in group 1.

Jg ^ É ^ - ^ á ^^ Group 27 In this case Ar has, by way of example, the meanings indicated in group 1. Group 28.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 29.

In this case Ar has, by way of example, the meanings indicated in group 1.

Group 30 In this case Ar has, by way of example, the meanings indicated in group 1. Group 31.

In this case Ar has, by way of example, the meanings indicated in group 1. Group 32.

In this case Ar has, by way of example, the meanings indicated in group 1. The new substituted phenylpyridazinones of the general formula (I) are obtained, if - - (a) halocarnanes of the general formula (II) are reacted wherein R1, R2 and R3 have the meaning indicated above and X1 means halogen, with pyridazinones of the general formula (III), wherein R 4, R 3 and R 6 have the meaning indicated above, or with acid adducts or with alkali metal salts of the compounds of the formula (III), optionally in the presence of an auxiliary agent of the reaction and, in a given case, in the presence of a diluent, or if (b) arylhydrazines of the general formula (IV) are reacted wherein R ', R2 and R3 have the meaning indicated above, with β-trihalomethyl-enones of the general formula (V) where R4, R! and R6 have the meaning indicated above and X2 means halogen, optionally in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, or if (c) hydrazonocarboxylic acids of the formula are condensed with cyclisation general (VI) wherein R1, R2, R3, R ", R5 and R6 have the meaning indicated above, ie they are reacted with a water scavenging agent, or if (d) they are nitrated 2,4-disubstituted phenyl-pyridazinones of the formula general wherein R ', R2, R \ R5 and R6 have the meaning indicated above, ie they are reacted with a nitrating agent, or if (e) hydrazonocarbonyl compounds of the general formula (VII) are reacted wherein R1, R2, R3, Rs and R6 have the above-indicated meaning, with alkoxycarbonylmethylenephosphorans of the general formula (VIII) COOR ^ P (C6H5) 3 (VIII) wherein R 4 has the meaning indicated above and R means alkyl having 1 to 6 carbon atoms, or with trialkyl phosphonocarboxylates of the general formula (IX) COOR R POOR). X) wherein R 4 has the meaning indicated above and R means alkyl having from 1 to 6 carbon atoms, respectively, optionally in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent. The compounds of the general formula (I) can also be transformed, - according to other usual methods, in other compounds of the general formula (I) according to the above definition, for example by nucleophilic substitution (for example R3: F? OH, SH, NH2, OCH3, NHSO2CH3) or by other transformations of the functional groups (for example R2: F / CIBr? CN, CONH2? CN, CN? CSNH2, NO2? NH2; R3: NO2? NH2, NH2? F, Cl, Br, CN, NHSO2CH3, SO2CI, OCH3? OH, OH ? 0CH2CH = CH2) -see also the procurement examples. If, for example, 4-fluoro-6-methyl-5-trifluoromethyl-pyridazin-3-one and 4,5-difluoro-2-methoxy-benzonitrile are used as starting materials, the development of the reaction may be schematized in the case of the process (a) according to the invention by means of the following formula scheme: If, for example, 4,4,4-trichloro-3-methyl-2-difluoromethyl-crotonaldehyde and 4-cyano-2-fluoro-5-propargylloxy-phenylhydrazine are used as starting materials, the development of the reaction in the case of process (b) according to the invention by means of the following formula scheme: If, for example, N- (4-cyano-2-fluoro-methylsulfonylamino-phenyl) -hydrazone of 2-chloro-3-chlorodifluoromethyl-4-oxo-2-butenoic acid is used as starting material, the development of the reaction in the case of process (c) according to the invention by means of the following formula scheme: If, for example, 2- (2-chloro-4-cyano-phenyl) -4,6-dichloro-5-pentafluoroethyl-pyridazin-3-one and nitric acid are used as starting materials, the development of the reaction in the case of process (d) according to the invention by means of the following formula scheme: ^^^^^^^^^^^^ - ^ - - If, for example, 3,3,3-trifluoro-2-oxo-propanal-1- (4-cyano-2,5-diflorophenylhydrazone) and triphenylphosphoranylidene-ethyl acetate are used as starting materials, the development of the reaction in the case of process (e) according to the invention by means of the following formula scheme.

The halo haloarins, to be used as starting materials in the case of the process (a) according to the invention, for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In formula (II), R1, R2 and R3 preferably have or especially that meaning which has already been indicated above, preferably or particularly preferably for R1, R2 and R3 in the description of the compounds of the formula ( I) to be prepared according to the invention; preferably X1 means fluorine, chlorine or bromine, especially fluorine The starting materials of the formula (II) are known and / or can be prepared according to processes known per se (cf. EP 191181, EP 370332, EP 431373, EP 441004). The pyridazinones to be further employed as starting materials in the case of process (a) according to the invention are generally defined by the formula (III). In the formula (III), R4, R5 and R6 preferably have that meaning which has been previously indicated preferably, particularly preferably or very particularly preferably for R ", R" and R6 in the description of the compounds of the formula (I) to be prepared according to the invention 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 arylhydrazines to be used as starting materials in the case of the process (b) according to the invention, for the preparation of the compounds of the formula (I) are generally defined by the formula (IV). In the formula (IV), R1, R2 and R3 preferably have that meaning which has been previously indicated in a preferred manner, particularly preferably or in a very special way e for R1, R2 and R3 in the description of the compounds of the formula (I), to be prepared according to the invention. The starting materials of the formula (IV) are known and / or can be prepared by processes known per se (cf. EP 370332). The β-trihalomethyl-enones to be used further as starting materials, in the process (b) according to the invention, are generally defined by the formula (V). In the formula (V), R4, Rs and R6 preferably have that meaning which has been previously indicated in a preferred manner, particularly preferably or very particularly preferably for R ", R5 and R6 in the description of the compounds of the formula (I), to be prepared according to the invention; X2 means fluorine, chlorine or bromine, especially chlorine The starting materials of the formula (V) are known and / or can be prepared by processes known per se (cf. DE 2706700). The hydrazonocarboxylic acids to be used as products of In the case of the process (c) according to the invention, for the preparation of the compounds of the formula (I), they are defined in general by the formula (VI): In the formula (VI), R ', R2 , R3, R4, R5 and Rs preferably have that meaning which has been previously indicated in a preferred manner, more preferably or very particularly preferably for R1, R2, R3, R ", R5 and R6 in the Description of the compounds of the formula (I), to be prepared according to the invention. The starting materials of the formula (VI) are known and / or can be prepared by processes known per se (see WO 9639392). The hydrazonocarboxylic acids of the general formula (VI) are obtained if they are reacted arylhydrazines of the general formula (IV) wherein R1, R2 and R3 have the meaning indicated above, with β-carboxy-enones of the general formula (X) wherein R 4, R 5 and R 6 have the meaning indicated above, if appropriate in the presence of a diluent, such as for example ethanol, and optionally, in the presence of an auxiliary agent of the reaction, such as, for example, p -toluenesulfonic, at temperatures between 0 ° C and 100 ° C. The 2,4-disubstituted phenyl-pyridazinones, to be used as starting materials in the process (d) according to the invention, for the preparation of the compounds of the formula (I), are generally defined by the formula (la) . In the formula (la), R ', R2, R \ R! and R.sup.6 preferably have that meaning which has been previously indicated in a preferred manner, more preferably or very particularly preferably for R ', R2, R ", R5 and R6 in the description of the compounds of the formula (I) , to be prepared according to the invention The starting materials of the formula (Ia) are known and / or can be prepared according to processes known per se (see the processes according to the invention (a) to (c)) The hydrazonocarbonyl compounds to be used as starting materials in the case of the process (e) according to the invention, for the preparation of the compounds of the formula (I), are generally defined by means of the formula (VII). In the formula (VII), R1, R2, R3, R5 and R6 preferably have or especially those meanings which have been previously indicated in a preferred manner, more preferably or very particularly preferably for R1, R2, R3, R5 and R6 in relation to the description of the compounds of the formula (I) according to the invention. The starting materials of the formula (VII) are known and / or can be prepared according to processes known per se (see WO 9707104). They are not yet known from the literature and constitute, as new compounds, an object of the present application, the hydrazonocarbonyl compounds of the general formula (Vlla) where R 'means fluorine, chlorine or bromine, R2"means cyano, carbamoyl, thiocarbamoyl, or means alkyl, alkoxy or alkylthio having respectively 1 or 2 carbon atoms, respectively substituted, if appropriate, by fluorine and / or by chlorine , R3 means the grouping -A'-A2-A3, in which A1 means a single bond, means oxygen, sulfur, -SO-, -SO2-, -CO- or means the grouping -N-A4-, where A4 means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkene with 3 to 4 carbon atoms, alkynyl with 3 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, femlo, alkylsulfonyl with 1 to 4 carbon atoms or femlsulfome, A1 it further means alkane with 1 to 6 carbon atoms, alkenodide with 2 to 6 carbon atoms, azaalkenodon with 2 to 6 carbon atoms, alkynnol with 2 to 6 carbon atoms, cycloalkanodon with 3 to 6 carbon atoms, cycloalkenodon with 3 to 6 carbon or femlene atoms substituted, respectively, by fluorine, chlorine or bromine, A2 means a single bond, means oxygen, sulfur, -SO-, -SO2-, -CO-, or the meaning grouping - N-A4-, where A4 means hydrogen, hydroxy, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl, alkylsulfomyl having 1 to 4 carbon atoms or femlsulfome, A2 also means alkanoyl with 1 to 6 carbon atoms, alkenodon with 2 to 6 carbon atoms, azaalkenodiyl with 2 to 6 carbon atoms, alkyl with 2 to 6 carbon atoms, cycloalkanodon with 3 to 6 carbon atoms, cycloalkenodon with 3 to 6 carbon atoms or femlene substituted, where appropriate, by fluorine, chlorine or bromine, A3 means hydrogen, hydroxy, amino, cyano, isocyano, thiocyanate, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, means alkyl, alkoxy, alkyl, alkylsulfite, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarboxy or "alkoxy" (thio) phosphono, with, respectively, 1 to 6 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by fluorine, by chlorine or by alkoxy with 1 to 4 carbon atoms, means alkene, alkenyloxy, alchemlamino, alkylidenamino, alchemloxycarbonyl, alkylo, alkyloxy, alkylamino Or alkyloxycarbomam with, respectively, 2 to 6 carbon atoms in the alkenyl, alkydene or alkynyl groups, respectively substituted, if appropriate, by fluorine or chlorine, means cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkyne diamino, cycloalkyloxycarboxy or cycloalkylalkoxycarbonyl with, respectively, 3 to 6 carbon atoms in the cycloalkyl groups and, optionally, 1 to 4 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by fluorine, by chlorine, by cyano, by carboxy, by alkyl with 1 to 4 carbon atoms and / or by alkoxycarbonyl having 1 to 4 carbon atoms, or means phenyl, femloxy, phenyl-C 1 -C 4 -alkyl, fem-C 1 -C 4 -alkoxy, phenyloxycarbonyl or fem-alkoxycarbonyl having 1 to 4 carbon atoms, each optionally substituted by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, by alkyloxy with 1 to 4 carbon atoms, by haloalkyloxy with 1 to 4 carbon atoms and / or by alkoxy-carbonyl with 1 to 4 carbon atoms, also means pyrrolyl, pyrazole, ylidazolyl, tpazoyl, fuplo, oxiranyl, oxetanyl dioxolamlo, time, oxazole, isoxazolyl, thiazolyl, isothiazolyl, oxadiazole, nadiazolyl, pipdmilo, pyrimidimide, tpazimlo, pyrazolyl-alkyl with 1 to 4 carbon atoms, funl-alkyl with 1 to 4 carbon atoms, thienyl-alkyl with 1 to 4 carbon atoms, oxazohl-alkyl with 1 to 4 carbon atoms, isoxazole-C 1 -C 4 -alkyl, thiazole-C 1 -C 4 -alkyl, pipdinyl-C 1 -C 4 -alkyl, pyrimidiml-C 1 -C 4 -alkyl , pyrazolylmethoxy, furylmethoxy, if appropriate wholly or partly hydrogenated, means perhydropyranylmethoxy or pyridylmethoxy, R5 means hydrogen, cyano, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means alkyl, alkoxy, alkylthio, alkylamino or dialkylamino with, respectively, 1 to 4 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by fluorine and / or by chlorine, and R6 means hydrogen, cyano, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means alkyl, alkoxy, alkylthio, alkylamino or dialkylamino with, respectively, 1 to 4 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by fluorine and / or by chlorine.

The novel hydrazonocarbonyl compounds of the general formula (Vlla) are obtained, if (a) arylhydrazines of the general formula (IVa) are reacted wherein R ', R2'1 and R3 have the meaning indicated above, with α-dihalogen-carbonyl compounds of the general formula (XI) RßR Vt ?3C I) d wherein R5 and R6 have the meaning indicated above and X3 means halogen (especially chlorine or bromine), if appropriate in the presence of a diluent, such as, for example, water and, if appropriate, in the presence of an auxiliary agent of the reaction, such as, for example, sodium acetate, at temperatures between 0 ° C and 100 ° C (see the preparation examples), or if -in the case where R6 means hydrogen-, (ß) is diazotan arylamines of the general formula (XII) wherein R1, R2"'and R3 have the meaning indicated above, in the usual manner (for example by reaction with sodium nitrite and hydrochloric acid and / or acetic acid), the diazonium compounds, formed in this case, are made reacting, in a usual manner, with 1,3-dicarbonyl compounds of the general formula (XIII) wherein R5 has the meaning indicated above and - -R means alkyl (preferably methyl or ethyl), and the compounds, obtained in this case, of the general formula (XIV) wherein R, R1, R2"1, R3 and R5 have the meaning indicated above, are hydrolyzed and decarboxylated in a conventional manner, alkoxycarbonylmethylenephosphores or trialkyl phosphonocarboxylates to be further employed as starting materials in the case of the process (e) according to the invention, for the preparation of the compounds of the formula (I), they are generally defined by means of the formulas (VIII) or (IX) In the formulas (VIII) and (IX), R4 preferably has the meaning that has already been indicated above, preferably, particularly preferably or very particularly preferably for R4 in relation to the description of the compounds of the formula (I) according to the invention, preferably R means, respectively, alkyl having 1 to 4 carbon atoms, especially methyl or ethyl The starting materials of the formulas (VIII) and (IX) are chemical products for synthesis with The processes (a), (b), (c), (d) and (e) for the preparation of the compounds of the formula (I) are preferably carried out in the presence of a - diluent As diluents, inert organic solvents are generally suitable. Preferably, halogenated, alicyclic and aromatic hydrocarbons, if appropriate halogenated, are present, such as, for example, pentane, hexane, heptane, petroleum ether, herb, benzene, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), tpchloromethane (chloroform), or tetrachloromethane, dialkyl ethers, such as, for example, diethyl ether, dnsopropyl ether, diethyl-t-butyl ether, ethyl-t-butyl ether, methyl-t-pentylether (MTBE), ethyl-t-pentylether, tetrahydrofuran (THF), l, -d? oxane, ethylenegol-dimethylether or -diethylether, diethylene glycol-dimethyl ether or -diethylether, dialkyl ketones, such as, for example, acetone, butanone (methyl ethyl ketone), methyl? -propyl ketone or menthyl-butyl ketone, nitplos, such as, for example, acetomyl, propiomtplo, butyrylplo or benzomtplo, amides , such as for example N, Nd? met? l-formam? da (DMF), N, Nd? met? lacetam? da, N-methylformanihda, N-methyl-pyrrolidone or hexamethyl-phosphorotpamide, esters, such as for example methyl, ethyl, n- or? -propyl acetate, of n-, i- or s-butyl, sulfoxides, such as for example dimethylsulfoxide, alkanols, such as for example methanol, ethanol, n- or -propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether or monoethyl ether, diethylene glycol monomethyl ether or mono-ethyl ether, their mixtures with water or pure water. In the case of process (b) according to the invention, acetic acid is advantageously also used as a diluent The processes (a), (b) and (e) according to the invention for the preparation of the compounds of the formula (I) are preferably carried out in the presence of an auxiliary agent of the Suitable reaction agents as an auxiliary agent of the reaction are generally inorganic acid bases or acceptors or Usual organelles These preferably include acetates, amides, carbonates, bicarbonates, hydrides, hydroxides, alcoholates of alkali metals or alkaline earth metals, such as, for example, sodium, potassium or calcium acetate, lithium amide, sodium, potassium amide or of calcium, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, methanolate, ethanolate, n-o? -propanolate, n-, i-, s- or sodium or potassium t-butanolate, in addition also basic organic nitrogenous compounds, such as for example trimethylamine, tetylamine, tripropylamine, t-butylamine, ethyl- dusopropylamine, N, Nd? met? lc? clohex? lam? na, dicyclohexylamine, ethyl-dicyclohexylamine, N, Nd? met? l-an? l? na, N, Nd? met? l-benc? lam? na, pipdin, 2-methyl-3-met? l-, 4-met? l-, 2,4-d? met? l-, 2,6-d? met? l-, 3,4-d ? met? and 3,5-dunet? lp? pdma, 5-et? l-2-met? lp? pd? na, 4-d? met? lam? no-p? pd? na, N-methyl-pipepdine, 1,4-d? azab? c? clo [2,2,2] -octane (DABCO), 1,5-d? azab? c? clo [4,3,0] -non-5-ene (DBN) yl, 8-d? azab? c? clo [5,4,0] -undec-7-ene (DBU) The procedure (c ) according to the invention for the preparation of the compounds of the formula (I) is carried out in the presence of a water removing agent. In this case, the usual dehydrating agents, such as for example sulfuric acid, methanesulfonic acid, acid, are suitable. benzenesulfonam, p-toluenesulfonic acid, acetic anhydride and phosphorus oxide (V) The process (d) according to the invention for the preparation of the compounds of the formula (I) is carried out using a nitration agent In this case The usual filtration agents, such as, for example, nitric acid and mixtures thereof with auxiliary agents for use in mining, for example sulfuric acid, are suitable.

The reaction temperatures in carrying out the processes (a), (b), (c), (d) and (e) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 200 ° C, preferably between 0 ° C and 150 ° C, especially between 10 ° C and 120 ° C. The processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under higher pressure or at a lower pressure, generally 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 used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent, if appropriate in the presence of a reaction auxiliary agent, and the reaction mixture is stirred, in general, for several hours at the required temperature. The preparation is carried out according to usual methods (see the preparation examples). The active compounds according to the invention can be used as defoliants, desiccants, herbicidal agents and especially as weed killers. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants: Dicotyledonous weeds of the following types: Sinapis Lepidium, Galium, Stellaria, Matricaria, Antherms, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, 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. Cultivation of dicotyledonous species: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.The use of the active compounds according to the invention, however, is not limited in any way to these classes, but they also extend equally over other plants. The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and road installations and in roads and squares, with and without tree growth. In the same way, the compounds can be used to control weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, of tea, rubber oil palms, cocoa, berries and hops, on paths ornamental and sporty and on surfaces of meadows and to fight weeds selectively in mono-annual crops. The compounds according to the invention of the formula (I) show a potent herbicidal activity and a broad spectrum of activity when used in the field and on the aerial parts of the plants. The active ingredients can be converted into customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compound , as well as micro-encapsulations in polymer materials. These formulations are prepared in known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid excipients, where appropriate, using surfactants, that is, emulsifiers and / or dispersants and / o foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. Particularly suitable liquid solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane. , or paraffins, for example, fractions of crude oil, mineral and vegetable oils, alcohols such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water.

Suitable solid excipients are, for example, ammonium salts and the ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorilloma or diatomaceous earths and molten synthetic minerals, such as silicic acid, highly dispersed, aluminum oxide and silicates, as solid excipients for granulates are, for example, natural, broken and fractionated minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as inorganic and organic flours, as well as granulates of materials organic substances, such as sawdust, coconut-nut shells, corn ears and tobacco stems, as emulsifiers and / or foam generators are suitable, for example, non-ionic and ammonium emulsifiers, such as pohoxyethylenated esters of fatty acids , polyoxyethylenated ethers of fatty alcohols, such as, for example, alkylamylphenyl Lister, alkylsulphonates, alkyl sulphates, arylsulphonates, as well as albumin hydrolysates, as dispersants are suitable, for example, sulfuric leaching of lignin and methylcellulose. Adhesives such as carboxymethyl cellulose, natural and synthetic polymers, granules or granules, can be used in the formulations. in the form of latex, such as gum arabic, vinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalma and lecithin, and synthetic phospholipids. Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, can be used. titanium oxide, ferrocyanate blue and organic dyes, such as alizarin dyes, azo dyes and phthalocycline metal and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and eme - The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides for controlling weeds, ready-to-use preparations or tank mixtures being possible. Suitable mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulniron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benftiresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop- (ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromophenoxy, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinodon (-ethyl), Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butüo), 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, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazifop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, Flumetsulam, Flum? Clorac (-pentuo), Flumioxazm, Flumipropyn, Flumetsulam, Fluometuron, Fluorochlopdone, Fluoroglycofen (-et? Lo), Flupoxam, Flupropacil, Flurpyrsulfuron (-method, -sodium), Flurenol (-but?), Flundone, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluüuacet (meülo), Fluthiamide, Fomesafen, Glufosmate (-amomo), Glyphosate (-? soprop? lamomo), Halosafen, Haloxyfop (-etox? et? lo), Haloxyfop (-P- methyl), Hexazmone, Imazamethabenz (-met? lo), Imazamefhapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron, Ioxyml, Isopropahn, Isoproturon, Isouron, Isoxaben, Isoxachlotole, Isoxaflutole, Isoxapypfop, Lactofen, Lenacil, Linuron , MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Methoxuron, Metpbuzm, Metsulfuron (-meülo), Molmate, Monolmuron, Naproarulide, Naproparmde, Neburon, Nicosulfuron, Norflurazon , Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluo rfen, Paraquat, pelargonomic acid, Pendimethalin, Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Pr? rmsulfüron (-men), Prometryn, Propachlor, Propaml, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-et? lo), Pyrazolate , Pyrazosulfuron (-et? Lo), Pyrazoxyfen, Pypbenzoxim, Pypbuticarb, Pypdate, Pypm? Nobac (-met? Lo), Pypth? Obac (-sod? O), Qumchlorac, Qummerac, Quinoclamine, Qu? Zalofop (-P- et? lo), Qurzalofop (-P-tefuril), Rimsulfuron, Sethoxydim, Simazine, Sunetryn, Sulcotpone, Sulfentrazone, Sulfometuron (-met? lo), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide , Tmazopyr, Tmdiazimm, Th? Fensulfi? Ron (-met? Lo), Thiobencarb, Tiocarbazü, Tralkoxydim, Tpallate, Tnasulfuron, Tnbenuron (-met? Lo), Tnclopyr, Tpdiphane, Tnfluralm and Tpflusulfuron A mixture with other known active substances is also possible, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, nutrient substances of the plants and means for improving the structure of the ground. The active products can be used as such, in the form of their formulations or of the forms of application prepared therefrom by further dilutions, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The use is carried out in the usual way, for example, by watering, spraying, spraying, spreading. The active products according to the invention can be applied both before and after the outbreak of the plants. They can also be incorporated into the soil before sowing. The quantities of active product used can vary within a wide range. These depend fundamentally on the type of the desired effect. In general, the amounts used are between 1 g and 10 kg of active product per hectare of land surface, preferably between 5 g and 5 kg per hectare.

The preparation and use of the active substances according to the invention are deduced from the following examples: Preparation examples: Example 1.

Combine 5.0 g (18 mmol) of 3,3,3-trifluoro-2-oxo-propanal-1- (2,5-difluoro-4-cyano-phenylhydrazone) in 150 ml of toluene, at 8.7. g (26 mmol) of methyl- (triphenylphosphoranylidene) acetate and stirred for 3 hours at reflux temperature. The mixture is concentrated by evaporation in a rotary evaporator and the residue is recrystallized from isopropanol. 1.3 g (24% of theory) of 2- (2,5-difluoro-4-cyano-phenyl) -5-trifluoromethyl-pyridazin-3-one are obtained with a melting point of 143 ° C. Example 2 Combine 5.0 g (18 mmol) of 3,3,3-trifluoro-2-oxopropanal-1- (2,5-difluoro-4-cyano-phenylhydrazone) in 150 ml of toluene, with 9.4 g ( 26 immoles) of (1-ethoxycarbonylethylidene) -triphenylphosphorane and stirred for 3 hours at the reflux temperature. The mixture is concentrated by evaporation in a rotary evaporator and the residue is recrystallized from isopropanol. - - 2.41 g (42.5% of the theory) of 2- (2,5-difluoro-4-cyano-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one are obtained with a melting point of 135 ° C. In a manner analogous to that of Examples 1 and 2 and according to the general description of the preparation processes according to the invention, the compounds of the formula (I) indicated in Table 1 below can also be prepared.

Table 1: Examples of compounds of the formula (I).

- - - - - - - - - - - - - - - • »• - - • - - - - - - - - - - - - - - The compound indicated above in Table 1 as Example 10, can Prepare, for example, in the following way: Combine 2.0 g (6.1 mmol) of 2- (4-cyano-2-fluoro-5-methoxy-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one in 100 ml of dichloromethane , with 18.4 g (18.3 mmol) of boron tribromide (1 molar solution in dichloromethane), are stirred for 16 hours at 25 ° C, then 150 ml of water are added slowly, the organic phase is dried on sodium sulphate and concentrated by evaporation in the rotary evaporator. 1.8 g (94% of theory) of 2- (4-cyano-2-fluoro-5-hydroxy-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one are obtained with a point of fusion of 189 ° C.

The compound indicated in Table 1 above by way of example 11 can be prepared, for example, in the following manner: Combine 3.9 g (13.5 mmol) of the 3,3,3-trifluoro-2-oxo-propanal-1- (4-cyano-2-fluoro-5-methoxy-phenylhydrazone) in 150 ml of toluene, with 7.0 g (19.3 mmol) of (l-ethoxycarbonyl-ethylidene) -triphenylphosphorane and stir for 2 hours, under argon, at reflux temperature. After concentration by evaporation in the rotary evaporator, the residue is recrystallized from isopropanol. 2.2 g (50% of theory) of 2- (4-cyano-2-fluoro-5-methoxy-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one are obtained with a point of 178 ° C fusion. The compound indicated above in Table 1 as Example 13 can be prepared, for example, in the following manner: 3.8 g (8 mmol) of 2- (4-bromo-2-fluoro-5-isopropoxy-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one are dissolved in 10 ml of N-methyl -pyrrolidone are combined with 0.9 g (9.6 mmol) of cuprous cyanide (I) and heated, under reduced pressure (0.1 mbar) to 90 ° C, whereby 2 ml of distillation are removed by distillation. solvent. It is then heated to 170 ° C under normal pressure (under argon) and stirred for 6 hours at this temperature. After cooling to 20 ° C, it is stirred with 100 ml of ethyl acetate, combined with 10% ammonia solution and filtered. The filtrate is washed with water, dried over sodium sulfate and carefully concentrated by evaporation under vacuum of the water tube. 3.0 g (89% of theory) of 2- (4-cyano-2-fluoro-5-isopropoxy-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one are obtained as a product raw (content: 85% according to HPLC). For a further purification, 2 g of this product are chromatographed in - 1- Crude through silica gel with dichloromethane. A pure product (0.7 g, content: 97% according to HPLC) with a melting point of 121 ° C is obtained. The compound indicated above in Table 1 as Example 15 can be prepared, for example, in the following manner: 0.6 g (1.9 mmol) of the 2- (4-cyano-2-fluoro-5-hydroxy-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one in 30 ml of N are stirred. , N-dimethyl formamide, with 0.4 g (3 mmol) of potassium carbonate and 0.31 g (2.1 mmol) of propargyl bromide (80%) for 60 minutes at 25 ° C, then they are combined with water, adjusted to pH 6 with concentrated hydrochloric acid, the precipitated product is filtered off by suction, washed with water and dried. For purification, it is recrystallized from isopropanol. 0.3 g (44% of theory) of 2- (4-cyano-2-fluoro-5-propargyloxy-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one are obtained with a point of fusion of 15 145 ° C. The compound indicated above in Table 1 as Example 18 can be prepared, for example, in the following manner: - - 0.7 g (2.24 mmol) of 2- (4-cyano-2-fluoro-5-hydroxy-phenyl) -4-methyl-5-trifluoromethyl-pipdazin-3-one are stirred in 30 ml. of N, N-dimethylformamide, with 0.48 g (3.5 mmol) of potassium carbonate and 0.42 g (2.5 mmol) of ethyl ethyl bromoacetate, for 60 minutes at 25 ° C. It is then combined with water, adjusted to pH 6 with concentrated hydrochloric acid, the precipitated product is separated by suction filtration, washed with water and dried. 0.64 g (71% of theory) of 2- [4-cyano-5- (ethoxycarbonylmethoxy) -2-fluoro-phenyl] -4-methyl-5-trifluoromethyl-pyridazin-3-one are obtained. with a melting point of 10 95 ° C. The compound indicated above in Table 1 as Example 41 can be prepared, for example, in the following manner: .5 g (15 mmol) of the 3,3,3-trifluoro-2-oxo-propanal-1- (4- 15 cyano-5-ethylsulfonylamino-2-fluoro-phenylhydrazone) are combined in 100 ml of toluene, with 9.2 g (22.5 mmol) of (l-ethoxycarbomethyl ethylidene) triphenylphosphorane and stir for 2 hours. - -hours, under argon, at the reflux temperature. After concentration by evaporation in the rotary evaporator, the residue is chromatographed on silica gel with toluene / ethyl acetate 3.1. 3.6 g (59.5% of theory) of 2- (4-cyano-5-ethanesulfonylamino-2-fluoro-phenyl) -4-methyl-5-trifluoromethyl-pyr-dazin-3-one are obtained. with a melting point of 198 ° C. The compound indicated above in Table 1 as Example 66 can be prepared, for example, in the following manner: 1.6 g (4 mmol) of the 2- (4-cyano-5-ethylsulphonylamino-2-fluoro-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one in 30 ml of pyridine are added. ml of triethylamine and is passed below the surface of the liquid, at 60-70 ° C, for 90 minutes, hydrogen sulfide. Once the reaction is complete, it is swept for 60 minutes with nitrogen, cooled to 25 ° C, stirred with ice water, the precipitated product is separated by filtration by suction, the residue is washed with water and dried. 0.9 g (51% of theory) of 2- (2-fluoro-5-ethylsulfonylamino-4-thiocarbamoyl-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one are obtained with a point of fusion of 88 ° C. The compound indicated above in Table 1 as Example 122 can be prepared, for example, in the following manner: - - 1.2 g (3 mmol) of 2- (4-cyano-5-ethylsulfonylamino-2-fluoro-phenyl) -4-methyl-5-trifluoromethyl-pyridazin-3-one are combined in 50 ml of acetonitop, with 0.6 g (6 mmol) of triethylamine and 0.77 g (6 mmol) of 3-chloro-propionyl chloride and stir for 12 hours at 25 ° C. After concentration by evaporation in the rotary evaporator, the residue is stirred with water, acidified with concentrated hydrochloric acid, the precipitated product is separated by suction filtration, washed with water and dried. 1.1 g of (2- [5- (N-ethylcarbonyl-N-ethylsulphonylamino) -4-cyano-2-fluoro-phenyl] -4-methyl-5-trifluoromethyl-pyridazin-3-one is obtained. with a melting point of 96 ° C. The compound indicated above in Table 1 as Example 129 can be prepared, for example, in the following manner: Combine 1.22 g (3.2 mmol) of the l - [(4-cyano-5-methylsulfonylamino-2-fluoro-phenyl) -hydrazono] -3-ethoxycarbonyl-1-chloro-1, 1-difluoro- propan-2-one, in 50 ml of toluene, with 1.74 g (4.8 mmoles) of (l-ethoxycarbomethyl ethylidene) triphenylphosphorane - and stirred for 2 hours, under argon, at reflux temperature. After concentration by evaporation in a rotary evaporator, the residue is chromatographed on silica gel with toluene / ethyl acetate 3: 1. 0.2 g (15% of theory) of 2- (4-cyano-5-ethanesulfonylamino-2-fluoro-phenyl) -4,6-dimethyl-5-trifluoromethyl-pyridazin-3-one are obtained with a point of fusion of 191 ° C. The compound indicated above in Table 1 as Example 107 can be prepared, for example, in the following manner: Combine 1.22 g (3.2 mmol) of the l - [(4-cyano-5-methylsulfonylamino-2-fluoro-phenyl) -hydrazono] -3-ethoxycarbonyl-1-chloro-1, 1-difluoro- propane-2-one, in 50 ml of toluene, with 1.7 g (4.8 mmol) of (l-ethoxycarbonyl-methylidene) -triphenylphosphorane and stir for 2 hours, under argon, at the reflux temperature. After concentration by evaporation in a rotary evaporator, the residue is chromatographed on silica gel with toluene / ethyl acetate 3: 1. 0.2 g (15.5% of theory) of 2- (4-cyano-5-ethylsulfonylamino-2-fluoro-phenyl) -6-methyl-5-trifluoromethyl-pyridazin-3-one are obtained with a melting point of 143 ° C. The physical data of the compounds indicated in Table 1 have been indicated in the table below.

- - Table la: - - - - The determination of the logP values indicated in Table 1 was carried out according to EEC Directive 79/831 annex V.A8 by HPLC (high performance liquid chromatography) on a column with phase inversion (C 18). Temperature • 43 ° C. (a) Eluents for the determination in the acid range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile -the corresponding measurement results have been marked in table 1 with ". (b) Eluents for the determination in the neutral range: 0.01 molar aqueous solution of phosphate buffer , acetonitrile, linear gradient from 10% acetonitrile to 90% acetonitrile - the corresponding measurement results have been marked in table 1. Calibration was carried out with unbranched alkane-2-ones (3 to 16). carbon atoms), whose logP values are known (determination of the logarithm values of P by means of the retention times by linear interpolation between two successive alkanones) The lambda-maximum values were determined by means of the UV spectra with 200 nm to 400 nm at the maximums of the chromatography signals.

- -Products of the formula ^ V): Example (IV-1).

At 15 ° C, 15 g (50 mmol) of 81% 4-cyano-2-fluoro-5-ethylsulfonylamino-aniline (known from DE-A-4414568) are cooled in a mixture with 100 ml of acetic acid and 20 ml of acetic acid. ml of concentrated sulfuric acid and combine, in portions, with 12.7 g (100 mmol) of nitrosylsulfuric acid and stir for 6 hours at 5 ° C to 10 ° C; then, dropwise, at 10 ° C, a solution of 33.6 g (140 mmol) of tin (II) chloride dihydrate dissolved in 15 ml of concentrated hydrochloric acid is added dropwise. The mixture is stirred for 12 hours at 25 ° C, then stirred with ice water and made alkaline with concentrated ammonia. The precipitated salt is filtered off with suction, the filtrate is slightly acidified with concentrated hydrochloric acid, extracted with ethyl acetate, dried over sodium sulphate and concentrated by evaporation in a rotary evaporator. The residue is recrystallized from isopropanol. 12.9 g (33% of theory) of 4-cyano-5-ethylsulphonylamino-2-fluoro-phenylhydrazine are obtained. 9.2 g (0.4 mol) of metallic sodium are dissolved in 200 ml of methanol and the solution is combined with 30.8 g (0.2 mol) of 2,5-difluoro-4-cyanoaniline. The stirring apparatus is equipped with a distillation equipment and heated to 90-95 ° C, with which approximately 4/5 of the amount of methanol is removed by distillation. After a further stirring time of 30 minutes at 95 ° C the heating is removed, the contents of the flask are combined with water, cooled to 25 ° C, adjusted to pH 5 with concentrated hydrochloric acid, the precipitated product it is separated by suction filtration, washed with water and dried. 31.2 g (94% of theory) of 4-cyano-2-fluoro-5-methoxy-aniline are obtained with a melting point of 99 ° C, purity (method): 99% (HPLC, logP 1 ,3. 4). 4.7 g (2.8 mmol) of 4-cyano-2-fluoro-5-methoxy-aniline are combined with 100 ml of concentrated hydrochloric acid and with 30 ml of water, heated briefly to 40 ° C and then it is refrigerated at 0 ° C. Then, dropwise, a solution of 2.6 g of sodium nitrite - dissolved in 30 ml of water - is added and the mixture is stirred for 60 minutes at 5 ° C to 10 ° C. It is then filtered and the filtrate is added dropwise at 0 ° C to a solution of 18 g (8 mmol) of tin (II) chloride dihydrate in 100 ml of concentrated hydrochloric acid. The suspension is then stirred for 60 minutes at room temperature (20 ° C), made alkaline with 45% sodium hydroxide solution and extracted several times with ethyl acetate. The organic phase is dried over sodium sulphate and concentrated by evaporation in a rotary evaporator under vacuum of the water tube. 3 g (60% of theory) of 4-cyano-2-fluoro-5-methoxy-phenylhydrazine are obtained with a melting point of 160 ° C. Second stage - variant b. - - 20 g (0.5 mol) of metallic sodium are dissolved in 400 ml of methanol and the solution is combined with 68 g (0.4 mol) of the 2,5-difluoro-4-cyano-phenylhydrazine. The stirring apparatus is equipped with a distillation equipment and heated to 80 ° C to 85 ° C, whereby approximately 80% of the methanol is distilled off. After a further stirring time of 3 hours at 85 ° C the heating is removed, the contents of the flask are combined with water, cooled to 25 ° C, neutralized with concentrated hydrochloric acid, the precipitated product is separated by filtration by suction, it is washed with water and dried. For the purification, it is recrystallized from ethanol. This gives 39 g (54% of theory) of 4-cyano-2-fluoro-5-methoxy-phenylhydrazine with a melting point of 163 ° C. Starting products of the formula (VII). Example (VII-1). g (370 mmoles) of sodium acetate are placed in 200 ml of water. Under ice-cooling, 25 g (93 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone are added dropwise and the mixture is stirred for 30 minutes at room temperature (approximately 20 ° C). It is then combined with 12 g (72 mmoles) of 2,5-difluoro-4-cyano-phenylhydrazine and the reaction mixture is stirred for 2 hours at 40 ° C to 50 ° C. The precipitated product is separated by Filtration by cold suction, washed with water and dried. 19 g (95.4% of theory) of 3,3,3-trifluoro-2-oxopropanal-1- (2,5-difluoro-4-cyano-phenylhydrazone) with a melting point of 181 ° are obtained. C. Example (VII-2).

Combine 7 g (87 mmol) of sodium acetate in 100 ml of water with 5.94 g (22 mmol) of 1, 1-dibromo-3,3,3-trifluoroacetone, stir for 30 minutes at room temperature. environment (approximately 20 ° C), combine with 3.0 g (17 mmol) of 4-cyano-2-fluoro-5-methoxy-phenylhydrazine, stir for 60 minutes at 40 ° C to 50 ° C and for 10 minutes at 40 ° C. minutes at 95 ° C. After cooling to 20 ° C the precipitated product is separated by suction filtration, washed with water and dried. 4.1 g (83% of theory) of 3,3,3-trifluoro-2-oxo-propanal-1- (4-cyano-2-fluoro-5-methoxy-phenhydrazone) are obtained with a melting point of 168 ° C. Example (VII-3). 4.1 g (50 mmol) of sodium acetate in 50 ml of water are stirred, with 3.6 -g of l, l-dibromo-3,3,3-trifluoro-acetona > for 30 minutes at 80 ° C, at 25 ° C, combine with 2.58 g (10 mmol) of 4-cyano-5-ethylsulfonymymino-2-fluoro-phenylhydrazine, stir for 90 minutes at 40 ° C until 50 ° C, they are cooled to 10 ° C, the precipitated product is separated by suction filtration, washed with water and dried. 3.03 g (83% of theory) of the 3,3,3-trifluoro-2-oxopropanal-1- (4-cyano-5-ethylsulfonylamino-2-fluoro-phenylhydrazone) with a melting point of 127 ° are obtained. C. Example (VII-4). 4.1 g (50 mmol) of sodium acetate in 50 ml of water are stirred with 3.6 g of 3,3-dibromo-1,1,1-trifluoro-2-butanone for 30 minutes at 80 °. C, at 25 ° C, combine with 2.58 g (10 mmol) of 4-cyano-5-ethylsulfonylamino-2-fluoro-phenylhydrazine, stir for 2 hours at 40 ° C to 50 ° C, refrigerate at 10 ° C. The precipitated product is separated by suction filtration, washed with water and dried. 3.2 g (84.2% of the theory) of l, l, l-trifluoro-2-oxo-butanal-3- (4-cyano-5-ethylsulfonylamino-2-fluoro-phenylhydrazone) are obtained with a melting point of 2U ° C.

- - Starting products of the formula (XIV): 6.87 g (30 mmol) of the 4-cyano-5-methylsulfonylamino-2-fluoro-5-aniline are placed in 100 ml of acetic acid, at 20 ° C they are added, in portions, under ice-cooling, 4, 7 g (34 mmol) of nitrosylsulfuric acid (92%) and stir for 2 hours at 25 ° C. The mixture is added dropwise, then, to a suspension of 10.6 g (45 mmol) of ethyl pentafluoropropynyl acetate and 16.4 g (200 mmol) of sodium acetate in 200 ml of ethanol at 5-10 °. C is stirred for 10-12 hours at 25 ° C, stirred on water, the precipitated product is separated by suction filtration, washed with water and dried. For purification, it is recrystallized from isopropanol. 8.6 g (60.5% of theory) of l - [(4-cyano-5-methylsulfonylamino-2-fluoro-phenyl) -hydrazono] -4-ethoxycarbonyl-1, 1, 2 are obtained, 2-pentafluorobu-15 tano-3-one with a melting point of 165 ° C. 0 .7 g (47 mmol) of the 4-cyano-5-methylsulfonylamino-2-fluoro-aniline are placed in 100 ml of acetic acid, at 20 ° C they are incorporated, in portions, under ice-cooling, 7.3 g (53 mmoles) of nitrosylsulfuric acid (92%) and stirred for 2 hours at 25 ° C. The mixture is then added, dropwise, to a suspension of 14.2 g (71 mmol) of ethyl 1,1,1-difluorochloroacetate and 26 g (313 mol) of sodium acetate in 200 ml of ethanol a 5 ° C to 10 ° C, stirring for 12 hours at 25 ° C, stirring over water, the precipitated product is separated by suction filtration, washed with water and dried. 13.7 g (66% of theory) of l - [(4-cyano-5-methylsulfonylami-2-fluoro-phenyl) -hydrazono] -3-ethoxycarbonyl-1, 1-difluor-1-are obtained. chlorine-propan-2-one with a melting point of 175 ° C. Application examples: In the application examples, the following known compounds are used for comparative purposes: 2- (5-Amino-2,4-dichloro-phenyl) -5-methyl-3 (2H) -pyridazinone - known from WO 9639392. 4-Bromo-2- (2,4-dichloro-5-nitro-phenyl) -5-methyl-3 (2H) -pyridazinone - known from WO 9639392. 2- (5-Amino-2,4-dichloro-phenyl) -4-bromo-5-methyl-3 (2H) -pyridazinone - known from WO 9639392. - - 4- (2,4-Dichloro-5-nitro-phenyl) -5-methyl-3 (2H) -pyridazinone - known from WO 9639392. 2,5-Difluoro-4- (4-methyl-6-oxo-l (6H) -pyridazinyl) -benzonitrile - known from WO 9639392. Example A. Pre-bud test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Seeds are sown from the test plants in normal soil. After 24 hours, approximately, the soil is watered with the preparation of the active product.

In this case, the quantity of water per unit area is suitably constant. The concentration of the sprayable broths is chosen in such a way that the quantity of active product desired in each case is applied in 1000 liters of water per hectare. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated control. They mean: 0% = no effect (same as untreated controls). 100% = total destruction. In this test, for example, the compounds according to the preparation examples 1, 2, 12, 13, 24, 40, 41, 46, 66, 84, 107, 112, 120, 121, 122, 123, 124 show, 125, 126, 127, 128, 129 and 133 a considerably more potent effect against weeds. Than the known compounds (A), (B), (C), (D) and (E). Example B. Post-emergence test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Test plants, having a height of 5 to 15 cm, are sprayed with the preparation of the active product in such a way that the desired quantities of active compound per unit area are respectively applied. The concentration of sprayable broths is chosen in such a way that it is applied in 1,000 liters of water / ha - the quantity desired in each case of active product. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated controls. They mean: 0% = no effect (same as the untreated controls). 100% = total destruction. In this test, for example, the compounds according to Preparation Examples 1, 2, 12, 13, 24, 40, 41, 46, 66, 84, 107, 112, 120, 121, 122, 123 show, 124, 125, 126, 127, 128, 129 and 133 a considerably more potent effect against weeds. Than the known compounds (A), (B), (C), (D) and (E).

Example C Test with Phaedon larvae Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Cabbage leaves (Brassica olerácea) are treated by immersion in the preparation of active compound of the desired concentration and are covered with larvae of the horseradish leaf beetle (Phaedon cochleariae), while the leaves are still moist. After the desired time the destruction is determined in%. In this case 100% means that all beetle larvae were destroyed, 0% means that no beetle larvae were destroyed. In this trial they showed, for Examples of the compounds according to the preparation examples 1 and 2 are good activity. It is noted that in relation to this date, the best method known to the applicant, to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims

Bfhjpn-cee d-escrito la inverrp? N choró -pte-ede is re-lama caro fj-cp-sdad what ccp enicb? N the sig? I-nt s: 1.- F-rilrprirh7pn-nas aJ_stL uicias de la general formula (I) characterized in that R 1 signifies hydrogen, fluorine, chlorine or bromine, R 2 signifies cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or means alkyl, alkoxy or alkylthio with respectively 1 or 2 carbon atoms substituted respectively by fluorine and / or per chlorine, R3 means the grouping -A'-A2-A \ in which A1 means a single bond, means oxygen, sulfur, -SO-, -SO.-, -CO- or means the grouping -N-A4- , where A "means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkenyl with 3 to 4 carbon atoms, alkynyl with 3 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl, alkylsulfonyl with 1 to 4 carbon atoms or phenylsulfonyl, A 'also means alkanediyl having 1 to 6 carbon atoms, alkenodiyl having 2 to 6 carbon atoms, azaalkenediyl with 2 to 6 carbon atoms, alkynediyl with 2 to 6 carbon atoms, cycloalkanediyl with 3 to 6 carbon atoms, cycloalkenodiyl with 3 to 6 carbon atoms or phenylene - - substituted, where appropriate, by fluorine, chlorine or bromine, A2 means a single bond, means oxygen, sulfur, -SO, -SO2-, CO- or means the group -N-A4-, where A4 means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, femlo, alkylsulfonyl with 1 to 4 carbon atoms or femlsulfonyl, A2 also means a diallodist with 1 to 3 carbon atoms, alkenodon with 2 to 6 carbon atoms, azaalkenodon with 2 to 6 carbon atoms, alkynnol with 2 to 6 carbon atoms, cycloalkanodon with 3 to 6 carbon atoms, cycloalkenodon with 3 to 6 carbon atoms or femlene, respectively, optionally substituted by fluorine, chlorine, bromine or alkoxy with 1 to 4 carbon atoms, A3 means hydrogen, hydroxy, amino, cyano, isocyano, thiocyanate, nitro, formyl, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine means alkyl, alkoxy, alkylthio, alkylsulfimyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl, alkylaminocarbomyl, dialkylammocarbom or od? alkoxy (t? o) phospho- ne with, respectively, 1 to 6 carbon atoms in the alkyl groups, substituted respectively in in the case given by hydroxy, by fluorine, by chlorine, by alkoxy with 1 to 4 carbon atoms, by alkyl-carbomloxy with 1 to 4 carbon atoms or by alkoxy-carbomloxy with 1 to 4 carbon atoms, means alkenyl, uemloxy, alchemlamino, alkynylammonium, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkylamino or alkyloxycarbomam with, respectively, 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, respectively substituted, if appropriate, by fluorine or chlorine, means cycloalkyl, cycloalkanoxy, - - cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamine, cycloalkyne diamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, with, respectively, 3 to 6 carbon atoms in the cycloalkyl groups and, optionally, 1 to 4 carbon atoms in the alkyl groups , respectively substituted, if appropriate, by fluorine, by chlorine, by cyano, by carboxy, by alkyl with 1 to 4 carbon atoms and / or by alkoxycarbonyl having 1 to 4 carbon atoms, or by phenyl, femloxy, femyl-alkyl with 1 to 4 carbon atoms, phenyl-alkoxy with 1 to 4 carbon atoms, phenyloxycarbonyl or fem-alkoxycarbomam with 1 to 4 carbon atoms, optionally substituted respectively by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkyloxy with 1 to 4 carbon atoms, by halogenoalkyloxy with 1 to 4 carbon atoms and / or by alkoxycarbon with 1 to 4 carbon atoms, A3 also means pyrrolyl, pyrazole, midazole, tpazohlo, fuplo, oxiramlo, oxetanyl, dioxolane, dioxanyl, tiedo, oxazole, isoxazolyl, thiazole, isothiazolyl, oxadiazole, iaadiazole, pipdimide, pyrimidinyl, triazinyl, pyrazole-C1-C4alkyl, fupl-alkyl with 1 to 4 carbon atoms, tieml-alkyl with 1 to 4 carbon atoms, oxazohl-alkyl with 1 to 4 carbon atoms, isoxazole-alkyl with 1 to 4 carbon atoms, thiazole-alkyl with 1 to 4 carbon atoms , pipdiml-alkyl having 1 to 4 carbon atoms, pipmidiml alkyl with 1 to 4 carbon atoms, pyrazolemethoxy, fuplmethoxy, respectively wholly or partly hydrogenated, respectively, means perhydropyranylmethoxy or pipdylmethoxy, R "signifies hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, mtro, - hydroxy, mercapto, ammo, fluorine, chlorine, bromine, or means alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl with, respectively, 1 to 4 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by fluorine and or by chloro, R5 means hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkoxycarbonyl, respectively 1 to 4 carbon atoms, in the alkyl groups respectively substituted, if appropriate, by fluorine and / or chlorine, and R6 means hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or alkyl, alkoxy, alkylthio, alkylamine, dialkylamine or alkoxycarbonyl having, respectively, 1 to 4 carbon atoms in the alkyl groups substituted, respectively, respectively by fluorine and / or by chlorine 2-substituted Femlpipdazinones according to n claim 1, characterized in that R1 signifies hydrogen, fluorine or chlorine, R2 signifies cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or tpfluromethyl, R3 signifies the grouping -A'-A2-A3, in which A 'signifies a simple bond, means oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -N-A4-, where A4 means hydrogen, hydroxy, methyl, ethyl, n- or? -propyl, methoxy, ethoxy, n- or? -propox ?, methylsulfonyl or ethylsulfomyl, -A1 also means methylene, ethane-1,1-dnon, ethane-1, 2-dnon, propane-1,1-dulo, propane-1, 2-dnon, propane-1, 3-dnon, ethene-1, 2-dnlo, propene-1,2-dnlo, propene-l, 3-dnlo, ethmo-l, 2-dial, propino-1,2-dulo or propino-ladillo, A2 means a single bond, means oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -N-A4-, where A4 means hydrogen, hydroxy, methyl, ethyl, n- or? -propyl, methoxy, ethoxy, n- or? -propox ?, methylsulfonyl, ethylsulfomyl, n- or? -prop? lsulfon? lo or femlsulfoml, A2 also means methylene, ethane-1,1-dnl, ethane-l, 2-dnl, propane-1,1- dnlo, propane-1,2-dnlo, propane 1,3-dnlo, etheno-l, 2-dnlo, propene-1,2-dnlo, propene-l, 3-dnlo, ethmo 1,2-dulo, prop? no-1, 2-dnor or prop-1,3-dulo, A3 means hydrogen, hydroxy, amino, cyano, nitro, formyl, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, means methyl, ethyl, n - or 1-propyl, n-, 1-, s- or t-butyl, n-, 1-, s- or t-pentyl, methoxy, ethoxy, n- or 1- propoxy, n-, 1-, s - or t-butoxi, n-, 1-, s- or t- pentyloxy, methylthio, ethyl, n- or 1-propylthio, n-, 1-, s- or t-butylthio, methylsulfimyl, ethylsulfimyl, n- or 1-propylsulfimyl, methylsulfomyl, ethylsulphonyl, n- or? -prop-lsulfon? It is methylamino, ethylamino, n- or 1-propylamine, n-, 1-, s- or t-butylamino, dunethylamino, diethylamino, methoxycarbonyl, ethoxycarbon, n- or 1-propoxycarbonyl, dimethoxyphospho, diethoxyphosphono or dipropoxyphospho- dnsopropoxyphosphoryl substituted, where appropriate, by fluorine, chlorine, methoxy or ethoxy, means etemol, propemyl, butemyl, propemloxy, butemloxy, propemlamino, butemlamino, propihdenammo, butihdenamino, propemloxycarbomlo, butemloxycarbomlo, etimlo, - propyl, butyl, propimloxy, butyloxy, propylamino, butylamino, propyloxycarbonyl or butynyloxycarbonyl respectively substituted, if appropriate, by fluorine or by chlorine, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl , cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexyhdenamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbomyl or cyclohexylmethoxycarbomide respectively substituted, where appropriate, by fluorine, by chlorine, by cyano, by carboxy, by methyl, by ethyl, by n- or 1-propyl, by methoxycarbonyl or by ethoxycarbonyl, or means femlo, femloxy, benzyl, femlethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl respectively substituted, where appropriate, by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine , for methyl, for ethyl, by n- or? -propyl, by tpflumomethyl, by methoxy, by ethoxy, by n- or? -propox ?, by difluoromethoxy, by trifluoromethoxy, by methoxycarbom and / or by ethoxycarbonyl, A3 also means dioxolamyl, dioxanyl, pyrrole, pyrazolyl, imidazolyl, tpazoyl, fuplo, time, oxazole, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazole, pipdimyl, pyrimidyl, tpazimyl, pyrazylmethyl, fuplmethyl, tiemlmethyl, oxazohlmethyl, isoxazolmethyl, thiazolmethyl, pipdinilmethyl. , pipmidinylmethyl, pyrazolemethoxy, fuplmethoxy or pyridylmethoxy (each case wholly or partly hydrogenated), R "means hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine or methyl, ethyl, n- - - i-propyl, n- i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl respectively substituted, if appropriate, by fluorine and / or by chlorine, R5 means hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl, respectively substituted, if appropriate, by fluorine and / or by chlorine, and Rd means hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, methoxycarbonyl or ethoxycarbonyl respectively substituted, if appropriate, by fluorine and / or by chlorine. 3. The substituted phenyl-pyridazinones according to claim 1, characterized in that R 'is hydrogen, fluorine or chlorine, R2 means cyano or thiocarbamoyl, R3 denotes the grouping -A'-A2-A3 where A1 means a single bond, means oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -N-A4-, where A4 means hydrogen, methyl, ethyl, n- or i-propyl, methylsulfonyl or ethylsulfonyl, A 'also means methyl, ethane-1, 1-diyl, ethane-1, 2-diyl, propane-1, 1-diyl, propene-1, 2-diyl, propane-1, 3-diyl, ethene-1, 2-diyl, propene-1, 2- diyl or propene-l, 3-diyl, -A2 means a simple bond, means oxygen, sulfur, -SO, -SO2-, -CO- or the crush -N-A4-, where A "means hydrogen, methyl, ethyl, n- or 1- propyl, methoxy , ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfomyl, n- or 1-propylsulfomyl or femlsulfonyl, A2 also means methylene, ethane-1,1-dnon, ethane-1, 2-dnon, propane-1,1- dnlo, propane-1,2 dnlo, propane-l, 3-dnlo, etheno-l, 2-dnlo, propene-1,2-dnlo or propene-l, 3-dnlo, A3 means hydrogen, hydroxy, amino, cyano , nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, means methyl, ethyl, n- or 1-propyl, n-, 1-, s- or t-butyl, n-, 1, s- or t- pentyl, methoxy, ethoxy, n- or i-propoxy, n-, 1-, t-butoxy, n-, 1-, s- or t-pentyloxy, methylthio, ethylthio, n- or l-propylthio, n- , 1-, s- or t-butylthio, methylsulfimyl, ethylsulphinyl, n- or β-propulsulfinyl, methylsulfomyl, ethylsulphyl, n-i-propylsulphyl, methylamino, ethylamino, n- or l-propylamino, n-, l -, s- or t-butylamm, dimethylamm, diethylamino, methoxycarbom, and Toxycarbonyl, n- or 1-propoxycarbonyl respectively substituted, if appropriate by fluorine, chlorine, methoxy or ethoxy, means propene, butenyl, propemloxy, butemloxy, propenylamino, butemlamino, propylidenammo, butynamino, propenyloxycarbonyl, butenyloxycarbomyl, propinyl, butyl, propyloxy, butymyloxy, propimamy, butynylamm, propyloxycarbomyl or butyloxycarbyl, respectively substituted by fluorine or chlorine, respectively, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy , cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentynylamino, - - cyclohexyhdepamino, cyclopentyloxycarbomyl, cyclohexyloxycarbomyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbomyl respectively substituted, where appropriate, by fluorineby chlorine, by cyano, by carboxy, by methyl, by ethyl, by n- or l-propyl, by meycarbulo or by eycarbom or to mean phenoxy, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbomyl or benzyloxycarbomyl respectively substituted, if appropriate by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- oipropyl, by tpflúormethyl, by mey, by ey, by nopropoxy, by difluoromey, by trifluoromey, by meycarbonyl and / or eycarbonyl, A3 further denotes pyrazolyl, imidazolyl, tpazoyl, fyl, time, oxazole, isoxazolyl, thiazolyl, isothiazolyl, oxadiazole, thiadiazole, pipimelim, pyrimidyl, tpazimyl, pyrazothylmethyl, fuplmethyl, tiemlmethyl, oxazohlmethyl, isoxazolylmethyl, thiazolmethyl, pipdimlmethyl, pyrimidimlmethyl, pyrazolemey, fuplmey or pipdylmey, R "means hydrogen, cyano, thiocarbamoyl, nitro, fluoro, chloro, bromo, or means methyl, ethyl, n-oi propyl, mey, ey, m ethylthio, ethylthio, methylamino, ethylamine or dimethylamine respectively substituted, if appropriate, by fluorine and / or chlorine, R 5 is methyl, ethyl, n- or 1-propyl substituted respectively by fluorine and / or chlorine, and R 6 is hydrogen, cyano , thiocarbamoyl, nitro, fluorine, chlorine, bromine, or means methyl, ethyl, n- or 1-propyl, mey, ey, methylthio, ethylthio, methylamino, ethylamine, dimethylamine, meycarbomyl or eycarbomide respectively substituted, if appropriate, by fluorine and / or or by chlorine 4 - . 4 - Substituted phenylpridazmonas according to one of claims 1 to 3, characterized in that R 1 is fluoro-substituted 5-Femlpipdazmonas according to one of claims 1 to 4, characterized in that R 2 represents substituted cyano-6-phenylpipdazinones according to one of claims 1 to 5, characterized in that R "and R6 are substituted hydrogen or methyl 7-phenylpipdazmonas according to any one of claims 1 to 6, characterized in that R5 is substituted p-trifluoromethyl 8-phenylpipdazinones according to one of claims 1 to 7, characterized in that R3 denotes A3 9-substituted phenylpipdazmone according to a of claims 1 to 8, characterized in that A1 means -NH- and A2 signified SO2 10-substituted phenylpipdazmone according to one of claims 1 to 9, characterized in that A 'means methylsulfonyl or ethylsulfomyl and A2 means -CO- 11 - Process for Obtaining femlpipdazmonas replaced according to one of the r claims 1 to 10, characterized in that (a) halogenarenes of the general formula (II) are reacted wherein R 1, R 2 and R 3 have the meaning indicated in one of claims 1 to 3 X 'halogen-specific, - with pyridazinones of the general formula (III), wherein R 4, R 5 and R 6 have the meaning indicated in one of claims 1 to 3 or with acid adducts or with alkali metal salts of the compounds of the formula (III), optionally in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, or in that (b) arylhydrazines of the general formula (IV) are reacted wherein R1, R2 and R3 have the meaning indicated in one of claims 1 to 3 with β-trihalomethyl-enones of the general formula (V) - wherein R ", R5 and Rs have the meaning indicated in one of claims 1 to 3 and X2 means halogen, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, or because (c) hydrazonocarboxylic acids of the general formula (VI) are condensed with cyclization wherein R ', R2, R3, R4, R5 and R6 have the meaning indicated in one of claims 3 that is to say that they are reacted with a water scavenging agent, or because (d) they are nitrated phenylpyridazinones 2,4 -disubstituted of the general formula (la) (the) wherein R1, R2, R ", R5 and R6 have the meaning indicated in one of claims 1 to 3, that is to say that they are reacted with a nitrating agent, or because (e) hydrazonocarbonyl compounds are reacted general formula (VII) wherein R1, R2, R3, R5 and Rfi have the meaning indicated in one of claims 1 to 3 with alkoxycarbonylmethylenephosphorans of the general formula (VIII) COOR R P (C = H ^ (VIII) wherein R 4 has the meaning indicated in one of claims 1 to 3 R means alkyl having 1 to 6 carbon atoms, or with trialkyl phosphonocarboxylates of the general formula (IX) - in which R 4 has the meaning indicated above and R means alkyl having from 1 to 6 carbon atoms, respectively, optionally in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent. 12.- Hydrazonocarbonyl compounds of the general formula (Vlla) characterized in that R1 represents fluorine, chlorine or bromine, R2"1" means cyano, carbamoyl, thiocarbamoyl, or means alkyl, alkoxy or alkylthio having 1 or 2 carbon atoms respectively, optionally substituted by fluorine and / or chlorine, R3 means the grouping -A '-A2- A3, in which A1 means a single bond, means oxygen, sulfur, -SO-, -SO2-, -CO- or means the grouping -N-A4-, where A4 means hydrogen , hydroxy, alkyl with 1 to 4 carbon atoms, alkenyl with 3 to 4 carbon atoms carbon, alkynyl with 3 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl, alkylsulfonyl with 1 to 4 carbon atoms or phenylsulfonylA1 also means alkanediyl with 1 to 6 carbon atoms, alkenodiyl with 2 to 6 carbon atoms, azaalkenodiyl with 2 to 6 carbon atoms, alkynediyl with 2 to 6 carbon atoms, cycloalkanediyl with 3 to 6 carbon atoms, cycloalkenodiyl with 3 to 6 carbon atoms or phenylene substituted, respectively where appropriate by fluorine, chlorine or bromine, A2 means a single bond, means oxygen, sulfur, -SO-, -SO2-, -CO-, or means grouping -N-A4-, where A4 means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl, alkylsulfonyl with 1 to 4 carbon atoms or phenylsulfonyl, A2 also means alkanediyl with 1 to 6 carbon atoms, alkenodiyl with 2 to 6 carbon atoms, azaalkenodiyl with 2 to 6 carbon atoms, alkynediyl with 2 to 6 carbon atoms, cycloalkanediyl with 3 to 6 carbon atoms, cycloalkenodiyl with 3 to 6 carbon atoms carbon or substituted phenylene optionally, fluorine, chlorine or bromine, A3 is hydrogen, hydroxy, amino, cyano, isocyano, thiocyanate, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl with, respectively, 1 to 6 carbon atoms in the alkyl groups, respectively substituted, where appropriate, by fluorine, by chlorine or by alkoxy with 1 to 4 atoms of carbon, means alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino - - 0-alkynyloxycarbonyl having, respectively, 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, respectively substituted if appropriate by fluorine or chlorine, means cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl with, respectively, 3 to 6 carbon atoms in the cycloalkyl groups and, optionally, 1 to 4 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by fluorine, by chlorine, by cyano, by carboxy, by alkyl with 1 to 4 carbon atoms and / or by alkoxycarbonyl with 1 to 4 carbon atoms, or means phenyl, phenyloxy, phenyl-alkyl with 1 to 4 carbon atoms, phenyl-alkoxy with 1 to 4 carbon atoms, phenyloxycarbonyl or phenyl-alkoxycarbonyl having 1 to 4 carbon atoms, each optionally substituted by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms carbon, by halogenalkyl with 1 to 4 carbon atoms, by alkyloxy with 1 to 4 carbon atoms, by haloalkyloxy with 1 to 4 carbon atoms and / or by alkoxycarbonyl with 1 to 4 carbon atoms, also means pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C 1 -C 4 -alkyl, furyl-alkyl with 1 to 4 carbon atoms, thienyl-alkyl with 1 to 4 carbon atoms, oxazolyl-alkyl with 1 to 4 carbon atoms, isoxazole-C 1 -C 4 -alkyl, thiazole-C 1 -C 4 -alkyl, pyridinyl-C 1 -C 4 -alkyl, pyrimidinyl-C 1 -C 4 -alkyl , pyrazolyl-methoxy, furylmethoxy, respectively, if appropriate, total or - - partially hydrogenated, means perhydropyranylmethoxy or pyridylmethoxy, R5 means hydrogen, cyano, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine, or means alkyl, alkoxy, alkylthio, alkylamino or dialkylamino with, respectively, 1 to 4 carbon atoms in the alkyl groups, substituted, if appropriate, by fluorine and / or chlorine, and R6 means hydrogen, cyano, thiocarbamoyl, nitro, hydroxy, mercapto, amino, fluorine, chlorine, bromine or alkyl, alkoxy, alkylthio, alkylamino or dialkylamm with, respectively, 1 to 4 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by fluorine and / or by chlorine. 13. - Plant protective agents, characterized in that they have a content in at least one substituted phenylpyridazinone according to one of claims 1 to 10 with customary extenders and / or surfactants. 14 -. 14 - Procedure for the control of undesirable plants or against animal pests, especially insects, characterized in that at least one substituted phenylpyridazinone according to one of claims 1 to 10 is allowed to act on the plants or on the animal pests and / or on their environment.