EP1272476A1

EP1272476A1 - 2-phenyl-2h-pyridazine-3-ones

Info

Publication number: EP1272476A1
Application number: EP01936233A
Authority: EP
Inventors: Michael Puhl; Thorsten Volk; Gerhard Hamprecht; Robert Reinhard; Ingo Sagasser; Cyrill Zagar; Karl-Otto Westphalen; Matthias Witschel; Helmut Walter
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 2000-04-14
Filing date: 2001-04-12
Publication date: 2003-01-08
Also published as: CA2406227A1; AU2001262197A1; WO2001079183A1; US20030130123A1

Abstract

The invention relates to 2-phenyl-2H-pyridazine-3-ones of general formula (I), wherein the variables R1, R2 and X have the following meanings: X represents halogen; R1 represents hydrogen or C¿1?-C4 alkyl, and; R?2¿ represents chlorine, OR?3 or NR4R5¿, wherein R?3, R4 and R5¿ have the meanings as cited in Claim No. 1. The invention also relates to the agriculturally suitable salts of compounds of formula (I). The invention additionally relates to the use of compounds (I) and the salts thereof as herbicides and/or for the desiccation and/or defoliation of plants, to herbicidal agents, and to agents for desiccating and/or defoliating plants, which contain, as active substances, compounds (I) and/or the salts thereof. Lastly, the invention relates to methods for controlling unwanted plant growth (harmful plants) and for the desiccation and/or defoliation of plants using compounds (I) and/or the salts thereof.

Description

2-phenyl-2H-pyridazin-3-one

description

The present invention relates to 2-phenyl-2H-pyridazin-3-one and the use thereof as herbicides and / or for the desiccation and / or defoliation of plants.

2H-Pyridazin-3-ones which have a phenyl substituent in the 2-position of the pyridazinone ring are variously described as herbicides in the prior art, for example in WO 96/39392, WO 97/07104, DE 19754348 and WO 99/52878. The compounds described therein generally have a substituent, for example a halogen atom, on the phenyl ring in the 2- and / or the 4-position, based on the pyridazinonyl radical. A side chain can be provided in the 5-position of the phenyl ring. Among other things, compounds are proposed which have an ethylenically unsaturated side chain derived from propenoic acid derivatives. The compounds described there have no α-halogen atom in the ethylenically unsaturated side chain.

The compounds of the prior art are often unsatisfactory in terms of their herbicidal activity and their selectivity. The object of the present invention was therefore to provide compounds with high herbicidal activity and selectivity.

It has surprisingly been found that certain 5-trifluoromethyl-2H-pyridazin-3-ones which have a phenyl ring in the 2-position of the pyridazinone ring, which has a chlorine atom in the 4-position and a side chain in the 3-position has, which is derived from an α-halopropenoic acid derivative, have a high herbicidal activity with simultaneous tolerance for crop plants.

Accordingly, the present invention relates to 2-phenyl-2H-pyridazin-3-ones of the general formula I.

where the variables R ¹ , R ² and X have the following meanings:

X halogen;

R ^{1 is} hydrogen or -CC ₄ alkyl;

R ^{2 is} chlorine, OR ³ or NR ⁴ R ⁵ , wherein

R ³ , R ⁴ independently of one another are hydrogen, C 1 -C ₄ -alkyl,

C 1 -C ₄ -haloalkyl, hydroxy-C 1 -C 4 -alkyl,

Cχ-C -alkoxy-Cι-C alkyl, cyano-Cχ-C alkyl,

-C -Alkylthio -C -C ₄ alkyl, C _! -C ₄ alkylsulfinyl-C _! -C ₄ alkyl,

C 1 -C ₄ alkylsulfonyl C 1 -C ₄ alkyl, amino C 1 -C 4 alkyl,

C 1 -C ₄ alkylamino C 1 -C ₄ alkyl,

Di- (Cχ-C ₄ -alkyl) amino -CC-C -alkyl,

Hydroxycarbonyl -CC -alkyl, (C ₁ -C -alkoxy) carbonyl-C ₁ -C ₄ -alkyl,

C 1 -C ₄ haloalkyloxycarbonyl C 1 -C ₄ alkyl,

Aminocarbonyl -CC ₄ -alkyl,

(-CC alkyl) aminocarbonyl -CC ₄ alkyl,

Di (C 1 -C 4 alkyl) aminocarbonyl C 1 -C ₄ alkyl, C 1 -C haloalkoxy-C ₄ -C ₄ alkyl,

Hydroxy-Cι-C -alkoxy-Cι-C ₄ alkyl,

-C -alkoxy-C ₁ -C -alkoxy -CC -alkyl,

Cyano-C 1 -C ₄ -alkoxy-C 1 -C ₄ -alkyl,

C ₁ -C ₄ -alkylthio -CC ₄ -alkoxy -CC ₄ -alkyl, -C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkoxy-C ₁ -C -alkyl,

-CC alkyl sulfonyl -CC ₄ -alkoxy -CC -alkyl,

Amino-Cι-C -alkoxy-Cι-C ₄ alkyl,

-CC alkylamino -CC alkoxy -CC -alkyl,

Di- (-C 1 -C 8) -alkyl-C 1 -C 8 -alkoxy-C 1 -C ₄ -alkyl, hydroxycarbonyl-C 1 -C 8 -alkoxy-Cι-C -alkyl,

(-C -alkoxy) carbonyl-C ₁ -C -alkoxy -CC-C ₄ -alkyl,

Aminocarbonyl-C ₁ -C ₄ alkoxy -CC-C ₄ alkyl, (C ₁ -C ₄ -alkyl) aminocarbonyl-C ₁ -C ₄ -alkoxy-Cι-C ₄ alkyl, di- (Cι-C alkyl) _{aminocarbonyl-Cι-C4-alkoxy-Cι-C} ₄ - alkyl , C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C alkenyloxy -CC-alkyl, C ₃ -C ₄ -alkynyloxy -CC ₄ -alkyl,

C ₃ -C ₄ alkenyloxycarbonyl -CC ₄ alkyl, C ₃ -C ₄ -alkynyloxycarbonyl -CC ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₈ -cycloalkyl -CC ₄ -alkyl, C ₃ -C ₈ cycloalkoxy -CC-C ₄ alkyl; and

R ^{5 is} hydrogen, -C ₄ alkyl, -C ₄ alkoxy, C ₃ -C ₆ alkenyl, C ₃ -C alkenyloxy, C ₃ -C ₆ alkynyl, C ₃ -C alkynyloxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl -CC ₄ -alkyl, C ₃ -C ₈ -cycloalkyl -CC ₄ -alkoxy mean;

R ⁴ and R ⁵ , together with the nitrogen atom to which they are attached, can mean a preferably saturated or unsaturated 3, 4, 5, 6 or 7-membered heterocyclic radical which selects 1 or 2 further, preferably non-adjacent, heteroatoms under oxygen and sulfur, and / or an I ino or -CC ₄ alkyl limino group as ring members and / or one or two substituents selected from halogen, -C ₄ alkyl and -C ₄ alkoxy may have ;

and the agriculturally useful salts of compounds of the formula I.

The invention further relates to

the use of compounds I and their salts as herbicides and / or for the desiccation and / or defoliation of plants, herbicidal compositions and agents for the desiccation and / or defoliation of plants which contain the compounds I and / or their salts as active substances, process to combat undesirable plant growth (harmful plants) and to desiccate and / or defoliate plants with the compounds I and / or their salts.

The invention also relates to diazanyl cinnamic acid compounds of the general formula II

wherein

R ^{2 has} the meaning given above and preferably represents a group OR ³ ,

R ^a and R ^{b are} simultaneously hydrogen or form a group = CH-C (0) -CF ₃

and the variables R ³ and X have the meanings given above. Among the compounds of the formula II, preference is given to those compounds in which R ^{2 is} selected from C 1 -C ₄ alkoxy. The compounds of the formula II are suitable intermediates for the preparation of the compounds of the general formula I according to the invention.

With regard to the double bond in the side chain, the compounds of the formula I can be present as E or Z isomers, based on the relative arrangement of the phenyl ring and halogen atom X. The compounds I according to the invention comprise both the pure E or Z isomers and their mixtures. The Z isomer is preferred, both in pure form and in the form of mixtures which contain the Z isomer in enriched form.

The compounds of the formula I can have one or more centers of chirality in the substituents and are then present as enantiomer or diastereomer mixtures. The invention relates both to the pure enantiomers or diastereomers and to their mixtures.

Agriculturally useful salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, the one to four C _if desired _! -C can carry alkyl and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, des furthermore phosphonium ions, sulfonium ions, preferably tri (Cι-C alkyl) sulfonium and sulfoxonium ions, preferably tri _(C! -C-alkyl) sulfoxonium, into consideration.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C ₄ -alkanoic acids, preferably Formate, acetate, propionate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The organic molecule parts mentioned in the definition of the substituents R ¹ - R ⁵ or as radicals on cycloalkyl rings - like the meaning halogen - are collective terms for individual lists of the individual group members. All carbon chains, that is to say all alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl , Aminoalkyl, cycloalkylalkyl, alkoxy,

Haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenyl and alkynyl groups and corresponding parts of groups in larger groups such as alkoxyalkyl, (di) alkylaminocarbonyl, alkoxycarbonyl, cycloalkoxyalkyl, alkoxycarbonylalkyl etc. can be straight-chain or branched, with the Prefix C _n -C _m indicates the possible number of carbon atoms in the group. Halogenated substituents preferably carry one, two, three, four or five identical or different halogen atoms. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine.

Furthermore, for example:

-C 1 -C ₄ alkyl for: CH ₃ , C ₂ H ₅ , n-propyl, CH (CH ₃ ) ₂ , n-butyl, CH (CH ₃ ) -C ₂ H ₅ , CH ₂ -CH (CH ₃ ) ₂ and C (CH ₃ ) ₃ ;

- _Cι-C4 haloalkyl of: which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine ₄ alkyl called a Cι-C as above, thus for. B. CHF, CHF ₂ , CF ₃ , CH ₂ C1, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl,

2,2,2-trichloroethyl, C ₂ F ₅ , 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3, 3-trifluoropropyl, 3,3, 3-trichloropropyl, 2,2,3,3, 3-pentafluoropropyl, heptafluoropropyl, 1- (Fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, l- (bromomethyl) -2-bromomethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;

- Hydroxy-Cχ-C ₄ alkyl for: z. B. Hydroxymethyl, 2-Hydroxyeth-1-yl, 2-Hydroxy-prop-l-yl, 3-Hydroxy-prop-l-yl, 1-Hydroxy-prop-2-yl, 2-Hydroxy-but-l- yl, 3-hydroxy-but-l-yl, 4-hydroxy-but-l-yl, l-hydroxy-but-2-yl, l-hydroxy-but-3-yl, 2-hydroxy-but-3- yl, l-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methyl-prop-3-yl or 2-hydroxymethyl-prop-2-yl, in particular for 2-hydroxyethyl;

Cyano -CC-alkyl for: z. B. cyanomethyl, 1-cyanoeth-l-yl, 2-cyanoeth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyano-prop-1-yl, l-cyanoprop- 2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l-yl, 1-cya-nobut- 2-yl, 2-cyanobut-2-yl, l-cyanobut-3-yl, 2-cyanobut-3-yl, l-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, especially for cyanomethyl or 2-cyanoethyl;

Amino -CC-C ₄ alkyl for: CH ₂ NH ₂ , 1-aminoethyl, 2-aminoethyl, 1-aminoprop-l-yl, 2-aminoprop-l-yl, 3-aminoprop-l-yl, 1-amino - but-l-yl, 2-aminobut-l-yl, 3-aminobut-l-yl, 4-aminobut-l-yl, l-aminobut-2-yl, 2-aminobut-2-yl, 3-aminobut -2-yl, 4-amino-but-2-yl, l- (CH ₂ NH ₂₎ eth-l-yl, 1- (CH2 _{_NH2)} -l- _(CH3) eth-l-yl or 1- (CH ₂ NH ₂ ) prop-1-yl;

- C ₁ -C ₄ alkylamino -CC-C-alkyl for: by -CC ₄ -alkylamino such as H ₃ C-NH-, H ₅ C ₂ -NH-, n-propyl-NH-, 1-methylethyl- NH-, n-butyl-NH-, 1-methylpropyl-NH-, 2-methylpropyl-NH- and 1,1-dimethylethyl-NH, substituted C _! -C -alkyl, for example for CH ₂ CH ₂ -NH-CH ₃ , CH ₂ CH ₂ -NH-C ₂ H ₅ , CH ₂ CH ₂ -NH-CH ₂ CH ₂ CH ₃ , CH ₂ CH ₂ -NH -CH (CH ₃ ) ₂ ;

- Di (C ₁ -C ₄ -alkyl) amino -CC ₄ -alkyl for: C Di-C-alkyl substituted by di (-C-C-alkyl) - amino, that is, for. For CH ₂ N (CH ₃ ) ₂ , CH ₂ N (C ₂ H ₅ ) ₂ , N, N-dipropylaminomethyl, N, N-Di [CH (CH ₃ ) ₂ ] aminomethyl, N, N- Dibutylaminomethyl, N, N-di- (l-methylpropyl) amino-methyl, N, N-di (2-methylpropyl) aminomethyl, N, N-di [C (CH ₃ ) ₃ ] aminomethyl, N-ethyl-N- methylaminomethyl, N-methyl1-N-propylaminomethyl, N-methyl1-N- [CH (CH ₃ ) ₂ ] aminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- (1-methylpropyl) aminomethyl, N-methyl -N- (2-methylpropyl) aminomethyl, N- [C (CH ₃ ) ₃ ] -N-methylaminomethyl, N-ethyl-N-propylaminomethyl, N-ethyl-N- [CH (CH ₃ ) ₂ ] aminomethyl, N-butyl-N-ethylaminomethyl, N-ethyl-N- (1-methylpropyl) aminomethyl, N-ethyl-N- (2-methylpropyl) aminomethyl, N-ethyl-N- [C (CH ₃ ) ₃ ] aminomethyl, N- [CH (CH ₃ ) ₂ ] -N-propyl-a inomethyl, N-butyl-N-propylaminomethyl, N- (1-methylpropyl) - N-propylaminomethyl, N- (2-methylpropyl) -N-propylaminomethyl, N- [C (CH ₃ ) ₃ ] -N-propylaminomethyl, N-butyl-N- (1-methylethyl) aminomethyl, N- [CH (CH ₃ ) ₂ ] - N- (1-methylpropyl) aminomethyl, N- [CH (CH ₃ ) ₂ ] -N- (2-methylpropyl) aminomethyl, N- [C (CH ₃ ) ₃ ] -N- [CH (CH ₃ ) ₂ ] aminomethyl, N-butyl-N- (1-methylpropyl) aminomethyl, N-butyl-N- (2-methylpropyl) aminomethyl, N-butyl-N- [C (CH ₃ ) ₃ ] - aminomethyl, N- (1- Methylpropyl) -N- (2-methylpropyl) aminomethyl, N- [C (CH ₃ ) ₃ ] -N- (1-methylpropyl) aminomethyl, N- [C (CH ₃ ) ₃ ] - N- (2-methylpropyl) aminomethyl, N, N-dimethylaminoethyl, N, N-di-ethylaminoethyl, N, N-di (n-propyl) aminoethyl, N, N-di- [CH (CH ₃ ) ₂ ] - aminoethyl, N, N-dibutylamino ethyl, N, -Di (1-methylpropyl) aminoethyl, N, N-Di (2-methylpropyl) aminoethyl, N, N-Di- [C (CH ₃ ) ₃ ] - aminoethyl, N-ethyl-N-methylaminoethyl, N-methyl-N-propylaminoethyl, N-methyl-N- [CH (CH ₃ ) ₂ ] aminoethyl, N-butyl-N-methylaminoethyl, N-methyl-N- (1-methylpropyl) aminoethyl, N -Methyl-N- (2-methylpropyl) aminoethyl, N- [C (CH ₃ ) ₃ ] -N-methylaminoethyl, N-ethyl-N-propylaminoethyl, N-ethyl-N- [CH (CH ₃ ) ₂ ] aminoethyl , N-butyl-N-ethylaminoethyl, N-ethyl-N- (1-methylpropyl) aminoethyl, N-ethyl-N- (2-methylpropyl) aminoethyl, N-ethyl-N- [C (CH ₃ ) ₃ ] aminoethyl , N- [CH (CH ₃ ) ₂ ] -N-propylaminoethyl, N-butyl-N-propylaminoethyl, N- (l-methylpropyl) -N-propylaminoethyl, N- (2-methylpropyl) -N-propylaminoethyl, N- [C (CH ₃ ) ₃ ] -N-prop 1-aminoethyl, N-butyl-N- [CH (CH ₃ ) ₂ laminoethyl, N- [CH (CH ₃ ) ₂ ] -N- (1-methylpropyl) aminoethyl , N- [CH (CH ₃ ) ₂ ] -N- (2-methylpropyl) aminoethyl, N- [C (CH ₃ ) ₃ ] -N- [CH (CH ₃ ) ₂ ] aminoethyl, N-butyl-N - (1-methylpropyl) aminoethyl, NB utyl-N- (2-methylpropyl) aminoethyl, N-butyl-N- [C (CH ₃ ) ₃ ] aminoethyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminoethyl, N- [C (CH ₃ ) ₃ ] -N- (1-methylpropyl) - aminoethyl or N- [C (CH ₃ ) ₃ ] -N- (2-methylpropyl) aminoethyl, especially for N, N-dimethylaminoethyl or N, N-diethylaminoethyl ;

C 1 -C ₄ -alkoxy-C ₄ -C ₄ alkyl for: CH ₂ -OCH ₃ , CH ₂ -OC ₂ H ₅ , n-propoxymethyl, CH ₂ -OCH (CH ₃ ) ₂ , n-butoxymethyl, (1- Methyl propoxy) methyl, (2-methyl propoxy) methyl, CH ₂ -OC (CH ₃ ) ₃ , 2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2- (n-propoxy) ethyl, 2- (l -Methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (l-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2- (1, 1-dimethylethoxy) ethyl, 2- ( Methoxy) propyl, 2- (ethoxy) propyl, 2_ (n-propoxy) propyl, 2- (l-methylethoxy) propyl, 2- (n-butoxy) propyl, 2- (l-methylpropoxy) propyl, 2- ( 2-methylpropoxy) propyl, 2- (1, l-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (n-propoxy) propyl, 3- (l-methylethoxy) propyl, 3- (n-butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methyl- propoxy) propyl, 3- (1, l-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (l-methylethoxy) butyl, 2- ( n-butoxy) butyl, 2- (l-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1, 1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl , 3- (n-propoxy) butyl, 3- (l-methylethoxy) butyl, 3- (n-butoxy) butyl, 3- (l-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1, l-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, 4- (l-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (l-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl or 4- (1, l-dimethylethoxy) butyl, preferably for CH ₂ -OCH ₃ , CH ₂ -OC ₂ H ₅ , 2- ( OCH ₃ ) ethyl or 2- (OC ₂ H ₅ ) ethyl;

- Cι-C -haloalkoxy-Cι ~ C ₄ alkyl: by Cι-C ₄ haloalkoxy, such as OCH ₂ F, OCHF _2, OCF _3, ₂ 0CH C1, OCH (Cl) _2, 0C (C1) _3, Chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro 2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC ₂ F ₅ , 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2 - chloropropoxy, 3-chloropropoxy, 2, 3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3, 3, 3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH ₂ -C ₂ F ₅ , OCF ₂ - C ₂ F ₅ , l- (CH ₂ F) -2-fluoroethoxy, 1- (CH ₂ Cl) -2-chloroethoxy, l- (CH ₂ Br) -2-bromethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4 -Bromobutoxy or nonafluorobutoxy, preferably for 0CHF ₂ , 0CF ₃ dichlorofluoromethoxy, chlorodifluoromethoxy or 2, 2, 2-trifluoroethoxy, substituted C 1 -C ₄ alkyl, that is, for. For 2- (OCHF ₂ ) ethyl, 2- (OCF ₃ ) ethyl or 2- (OC ₂ F ₅ ) ethyl;

Hydroxy-C ₄ -alkoxy-C 1 -C ₄ -alkyl: by hydroxy-Cχ-C ₄ -alkoxy such as 0CH ₂ 0H, 1-hydroxyethoxy, 2-hydroxyethoxy, 1-hydroxyprop-l-oxy, 2-hydroxyprop-l -oxy, 3-hydroxyprop-l-oxy, 1-hydroxybut-l-oxy, 2-hydroxybut-l-oxy, 3-hydroxybut-l-oxy, 4-hydroxybut-l-oxy, l-hydroxybut-2-oxy , 2-hydroxybut-2-oxy, 3-hydroxybut-2-oxy, 4-hydroxybut-2-oxy, l- (CH ₂ OH) eth-l-oxy, or l- (CH ₂ OH) prop-l- oxy-substituted -CC ₄ alkyl, so z. B. for 1-hydroxyethoxymethyl, l-hydroxyethoxy-2-ethyl;

- Cyano-C ₁ -C -alkoxy -CC ₄ -alkyl: by cyano -CC -alkoxy such as cyanomethoxy, 1-cyanoeth-l-oxy, 2-cyanoeth-l-oxy, 1-cyano-prop- 1-oxy, 2-cyanoprop-l-oxy, 3-cyanoprop-l-oxy, 1-cyano-prop-2-oxy, 2-cyanoprop-2-oxy, 1-cyanobut-

1-oxy, 2-cyanobut-l-oxy, 3-cyanobut-l-oxy, 4-cyanobut-l-oxy, l-cyanobut-2-oxy, 2-cyanobut-2-oxy, l-cyanobut-3- oxy, 2-cyano-but-3-oxy, l-cyano-2-methyl-prop-3-oxy, 2-cyano-2-methyl-prop-3-oxy, 3-cyano-2-methyl-prop- 3-oxy or 2-cyanomethyl prop-2-oxy substituted C 1 -C ₄ alkyl such as 2-cyanoethoxymethyl, 2- (2-cyanoethoxy) ethyl or 2- (2-cyanoethoxy) propyl;

- amino-Cι-C -alkoxy-Cι-C ₄ alkyl: -alkoxy by amino-Cι-C as A inomethoxy, 1-Aminoeth-l-oxy, 2-Aminoeth-l-oxy,

1-aminoprop-l-oxy, 2-aminoprop-l-oxy, 3-aminoprop-l-oxy, l-aminoprop-2-oxy, 2-aminoprop-2-oxy, 1-aminobut-1-oxy, 2- Aminobut-l-oxy, 3-aminobut-l-oxy, 4-aminobut-l-oxy, l-aminobut-2-oxy, 2-aminobut-2-oxy, l-aminobut-3-oxy, 2-aminobut- 3-oxy, l-amino-2-methyl-prop-3-oxy, 2-amino-2-methyl-prop-3-oxy, 3-amino-2-methyl-prop-3-oxy or 2- Aminomethyl prop-2-oxy substituted Cχ-C ₄ alkyl such as 2-aminoethoxy methyl, 2- (2-aminoethoxy) ethyl or 2- (2-aminoethoxy) propyl;

- Hydroxycarbonyl-C ₁ -C ₄ alkoxy-C ₁ -C ₄ -alkyl: C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl substituted by COOH in the alkoxy part, that is to say for -CH ₂ -0-CH ₂ COOH, -CH ₂ CH ₂ -0-CH ₂ COOH, -CH ₂ CH ₂ CH ₂ -0-CH ₂ COOH, -CH ₂ CH (CH ₃ ) -0-CH ₂ COOH, -CH (CH ₃ ) CH ₂ -0- CH ₂ COOH,

-CH ₂ -0-CH ₂ CH ₂ COOH, -CH ₂ CH ₂ -0-CH ₂ CH ₂ COOH, -CH ₂ CH ₂ CH ₂ -0-CH ₂ CH ₂ COOH, -CH ₂ CH (CH ₃ ) -0-CH ₂ CH ₂ COOH, -CH (CH ₃ ) CH ₂ -0-CH ₂ CH ₂ COOH, -CH ₂ -0-CH (CH ₃ ) COOH, -CH ₂ CH ₂ -0-CH (CH ₃ ) COOH, -CH ₂ CH ₂ CH ₂ -0-CH (CH ₃ ) COOH, -CH ₂ CH (CH ₃ ) -O-CH (CH ₃ ) COOH, -CH (CH ₃ ) CH ₂ -0- CH (CH ₃ ) COOH;

Aminocarbonyl-Cι-C alkoxy-C ₁ -C ₄ alkyl: by CONH ₂ substituted in the alkoxy part Cι-C -alkoxy-Cι-C ₄ alkyl eg -CH ₂ -0-CH ₂ CONH _2, -CH ₂ CH ₂ -0-CH ₂ CONH ₂ , -CH ₂ CH ₂ CH ₂ -0-CH ₂ CONH ₂ , -CH ₂ CH (CH ₃ ) -0-CH ₂ CONH ₂ , -CH (CH ₃ ) CH ₂ -0-CH ₂ CONH ₂ , -CH ₂ -0-CH ₂ CH ₂ CONH ₂ , -CH ₂ CH ₂ -0-CH ₂ CH ₂ CONH ₂ , -CH ₂ CH ₂ CH ₂ -0-CH ₂ CH ₂ CONH ₂ , -CH ₂ CH (CH ₃ ) -0-CH ₂ CH ₂ CONH ₂ , -CH (CH ₃ ) CH ₂ -0-CH ₂ CH ₂ CONH ₂ , -CH ₂ -0-CH (CH ₃ ) CONH ₂ , -CH ₂ CH ₂ -0-CH (CH ₃ ) CONH ₂ , -CH ₂ CH ₂ CH ₂ -0-CH (CH ₃ ) CONH ₂ , -CH ₂ CH (CH ₃ ) -O- CH (CH ₃ ) CONH ₂ , -CH (CH ₃ ) CH ₂ -0-CH (CH ₃ ) CONH ₂ ;

C ₁ -C ₄ alkylthio-C ₁ -C ₄ alkyl for: CH ₂ -SCH ₃ , CH ₂ -SC ₂ H ₅ , n-propylthiomethyl, CH ₂ -SCH (CH ₃ ) ₂ , n-butylthiomethyl, ( l-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH ₂ -SC (CH ₃ ) ₃ , 2- (methylthio) ethyl, 2- (ethylthio) ethyl, 2- (n-propylthio) ethyl, 2- ( 1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2- (1, 1-dimethylethylthio) ethyl, 2- (methyl - thio) propyl, 2- (ethylthio) propyl, 2- (n-propylthio) propyl, 2- (1-methylethylthio) propy1, 2- (n-butylthio) propyl, 2- (1-methylpropylthio) propyl, 2- (2-methylpropylthio) propyl, 2- (1, 1-dimethylethylthio) propyl, 3- (methylthio) propyl, 3- (ethylthio) propyl, 3- (n-propylthio) propyl, 3- (1-methylethylthio) propyl, 3- (n-butylthio) propyl, 3- (1-methylpropylthio) propyl, 3- (2-methylpropylthio) propyl, 3- (1, 1-dimethylethyl- thio) propyl, 2- (methylthio) butyl, 2- (ethylthio) butyl, 2- (n-propylthio) buty1, 2- (1-methylethylthio) butyl, 2- (n-butylthio) butyl, 2- (1- Methylpropylthio) butyl, 2- (2-methylpropylthio) utyl, 2- (1, 1-dimethylethylthio) butyl, 3- (methylthio) butyl, 3- (ethylthio) butyl, 3- (n-propylthio) butyl .

3- (l-methylethylthio) butyl, 3- (n-butylthio) butyl, 3- (l-methylpropylthio) butyl, 3- (2-methylpropylthio) butyl, 3- (1, 1-dimethylethylthio) butyl , 4- (methylthio) butyl, 4- (ethylthio) butyl, 4- (n-propylthio) butyl, 4- (1-methylethylthio) butyl, 4- (n-butylthio) butyl, 4- (1-methylpropylthio) butyl,

4- (2-methylpropylthio) butyl or 4- (1, 1-dimethylethylthio) butyl, preferably CH ₂ -SCH ₃ , CH ₂ -SC H ₅ , 2- (SCH ₃ ) ethyl or

2- (SC ₂ H ₅ ) ethyl;

C 1 -C 4 -alkyl sulfonyl-C 1 -C 6 -alkyl: for a C 1 -C 4 -alkyl sulfyl radical such as SO-CH ₃ , SO-C ₂ H ₅ , SO-CH ₂ -C ₂ H ₅ , SO-CH (CH ₃ ) ₂ , SO- (nC ₄ H ₉ ), SO-CH (CH ₃ ) -C ₂ H ₅ , SO-CH ₂ -CH (CH ₃ ) ₂ or SO-C (CH ₃ ) ₃ substituted Cι -C ₄ alkyl, for example for CH ₂ SO-CH ₃ , CH ₂ SO-C ₂ H ₅ , CH SO-CH ₂ -C ₂ H ₅ , CH ₂ SO-CH (CH ₃ ), CH ₂ SO-CH ₂ CH ₂ CH ₂ CH ₃ , CH ₂ SO-CH (CH ₃ ) -C ₂ H ₅ , CH ₂ SO-CH ₂ -CH (CH ₃ ) ₂ , CH ₂ CH ₂ SO-CH ₃ , CH ₂ CH ₂ SO-C ₂ H ₅ , CH ₂ CH ₂ SO-CH ₂ -C ₂ H ₅ , CH ₂ CH ₂ SO-CH (CH ₃ ) ₂ , CH ₂ CH ₂ SO-CH ₂ CH ₂ CH ₂ CH ₃ , CH ₂ CH ₂ SO-CH (CH ₃ ) -C ₂ H ₅ , CH ₂ CH ₂ SO-CH ₂ -CH (CH ₃ ) ₂ ;

C 1 -C ₄ alkylsulfonyl-C 1 -C ₄ -alkyl: for a through a C ₁ -C ₄ -alkylsulfonyl radical such as S0 ₂ -CH ₃ , S0 ₂ -C ₂ H ₅ , S0 ₂ -CH ₂ -C ₂ H ₅ , S0 ₂ -CH (CH ₃ ) ₂ , n-butylsulfonyl, S0 ₂ -CH (CH ₃ ) -C ₂ H ₅ , S0 ₂ -CH ₂ -CH (CH ₃ ) ₂ or S0 ₂ -C (CH ₃ ) ₃ , preferably S0 ₂ -CH ₃ or S0 ₂ -C ₂ H ₅ substituted C ₁ -C ₄ -alkyl, for example for CH ₂ S0 ₂ -CH ₃ , CH ₂ S0 ₂ -C ₂ H ₅ , CH ₂ S0 ₂ -CH ₂ - C ₂ H ₅ , CH ₂ S0 ₂ -CH (CH ₃ ) ₂ , CH ₂ S0 ₂ -CH ₂ CH ₂ CH ₂ CH ₃ , CH ₂ S0 ₂ -CH (CH ₃ ) -C ₂ H ₅ CH ₂ S0 ₂ -CH ₂ -CH (CH ₃ ) ₂ , CH ₂ CH ₂ S0 ₂ -CH ₃ , CH ₂ CH ₂ S0 ₂ -C ₂ H ₅ , CH ₂ CH ₂ S0 ₂ -CH ₂ -C ₂ H ₅ , CH ₂ CH ₂ S0 ₂ -CH (CH ₃ ) ₂ , CH ₂ CH ₂ S0 ₂ -CH ₂ CH ₂ CH ₂ CH ₃ , CH ₂ CH ₂ S0 ₂ -CH (CH ₃ ) -C ₂ H ₅ , CH ₂ CH ₂ S0 ₂ -CH ₂ -CH (CH ₃ ) ₂ ;

Hydroxycarbonyl -CC ₄ alkyl for: CH ₂ C00H, 1- (COOH) ethyl, 2- (COOH) ethyl, 1- (COOH) prop-l-yl, 2- (COOH) prop-l-yl, 3- (COOH) - prop-1-yl, l- (COOH) but-l-yl, 2- (COOH) but-l-yl, 3- (C00H) but-1-yl, 4- (C00H) but-l-yl, 1- (C00H) but-2-yl, 2- (C00H) but-2-yl, 3- (C00H) but-2-yl, 4- (COOH) but-2-yl, 1- (CH ₂ C00H) eth-l-yl, l- (CH ₂ COOH) -l- (CH ₃ ) -eth-l-yl or 1- (CH ₂ COOH) prop-l-yl;

(-C-C ₄ -alkoxy) carbonyl -CC-C ₄ -alkyl for: by (-C-C ₄ -alkoxy) carbonyl such as CO-OCH ₃ , CO-OC ₂ H ₅ , CO-OCH ₂ -C ₂ H ₅ , CO-OCH (CH ₃ ) ₂ , n-butoxycarbonyl, CO-OCH (CH ₃ ) -C ₂ H ₅ , CO-OCH ₂ -CH (CH ₃ ) ₂ or CO-OC (CH ₃ ) ₃ , preferably CO -OCH ₃ or CO- OC ₂ H ₅ substituted -CC-alkyl, for example for CH ₂ -CO-OCH ₃ , CH ₂ -CO-OC ₂ H ₅ , CH ₂ -CO-OCH ₂ -C ₂ H ₅ , CH ₂ -CO-OCH (CH ₃ ) ₂ , n-butoxycarbo- nylmethyl, CH ₂ -CO-OCH (CH ₃ ) -C ₂ H ₅ , CH ₂ -C0-0CH ₂ -CH (CH ₃ ) ₂ , CH ₂ -CO- OC (CH ₃ ) ₃ , l- (CO- OCH ₃ ) ethyl, 1- (CO-OC ₂ H ₅ ) ethyl, l- (CO-OCH ₂ -C ₂ H ₅ ) ethyl, 1- [CH (CH ₃ ) ₂ ] ethyl, 1- (n-butoxycarbonyl ) ethyl, 1- [1-methylpropoxycarbonyl] ethyl, 1- [2-methylpropoxycarbonyl] ethyl, 2- (CO-OCH ₃ ) ethyl, 2- (CO-OC ₂ H ₅ ) ethyl, 2- (CO-

OCH ₂ -C ₂ H ₅ ) ethyl, 2- [CO-OCH (CH ₃ ) ₂ ] ethyl, 2- (n-butoxycarbonyl) ethyl, 2- [1-methylpropoxycarbonyl] ethyl, 2- [2-methylpropo xycarbonyl] ethyl, 2- [CO-OC (CH ₃ ) ₃ ] ethyl, 2- (CO-OCH ₃ ) propyl,

2- (C0-0C ₂ H ₅ ) propyl, 2- (CO-OCH ₂ -C ₂ H ₅ ) propyl, 2- [CO-OCH (CH ₃ ) ₂ ] propyl 2- (n-butoxycarbonyl) propyl , 2- [1-methylpropoxycarbonyl] propyl, 2- [2-methylpropoxycarbonyl] propyl, 2- [CO-OC (CH ₃ ) ₃ ] propyl, 3- (CO-OCH ₃ ) propyl, 3- (CO-OC ₂ H ₅ ) propyl, 3- (CO-OCH ₂ -C ₂ H ₅ ) propyl, 3- [CO-OCH (CH ₃ ) ₂ propyl, 3- (n-butoxycarbonyl) propyl, 3- [1-methylpropoxycarbonyl] propyl, 3- [2-methylpropoxycarbonyl] propyl, 3- [CO-OC (CH ₃ ) ₃ ] propyl, 2- (CO-OCH ₃ ) butyl,

2- (CO-OC ₂ H ₅ ) butyl, 2- (CO-OCH ₂ -C ₂ H ₅ ) butyl, 2- [CO-OCH (CH ₃ ) ₂ ] butyl, 2- (n-butoxycarbonyl) butyl, 2- [1-methylpropoxycarbonyl] butyl, 2- [2-methylpropoxycarbonyl] butyl, 2- [CO-OC (CH ₃ ) ₃ ] butyl, 3- (CO-OCH ₃ ) butyl, 3- (CO-OC ₂ H ₅ ) butyl, 3- (CO-OCH ₂ -C ₂ H ₅ ) butyl, 3- [CO-OCH (CH ₃ ) ₂ ] butyl, 3- (n-butoxycarbonyl) butyl, 3- [1-methylpropoxycarbonyl ] butyl, 3- [2-methylpropoxycarbonyl] butyl, 3- [CO- OC (CH ₃ ) ₃ ] butyl, 4- (CO-OCH ₃ ) butyl, 4- (CO-OC ₂ H ₅ ) butyl, 4- (CO- OCH ₂ -C ₂ H ₅ ) butyl, 4- [CO-OCH (CH ₃ ) ₂ ] butyl, 4- (n-butoxycarbonyl) butyl, 4- [1-methylpropoxycarbonyl] butyl, 4- [2- Methylpropoxycarbonyl] butyl or 4- [CO-OC (CH ₃ ) ₃ ] butyl, preferably for CH ₂ -CO-OCH ₃ , CH ₂ -CO-OC ₂ H ₅ , 1- (CO-OCH ₃ ) ethyl or 1- (CO-OC ₂ H ₅ ) ethyl;

Aminocarbonyl -CC ₄ alkyl for: CH ₂ CONH ₂ , 1- (CONH ₂ ) ethyl, 2- (CONH ₂ ) ethyl, 1- (CONH ₂ ) prop-1-yl, 2- (CONH ₂ ) prop -l-yl, 3- (CONH ₂ ) prop-l-yl, l- (CONH ₂ ) but-l-yl, 2- (CONH ₂ ) but-l-yl, 3- (CONH ₂ ) but-l -yl, 4- (CONH ₂ ) but-l-yl, 1- (C0NH ₂ ) but-2-yl, 2- (CONH ₂ ) but-2-yl, 3- (CONH ₂ ) but-2-yl , 4- (CONH ₂ ) but-2-yl, l- (CH ₂ CONH ₂ ) eth-l-yl, l- (CH ₂ CONH ₂ ) -l- (CH ₃ ) -eth-l-yl or 1 - (CH ₂ CONH ₂ ) prop-1-yl;

(-CC alkylamino) carbonyl -CC alkyl for: by (-CC ₄ -alkylamino) carbonyl such as CO-NH-CH ₃ , CO-NH-C ₂ Hs, n-propylaminocabonyl, CO- NH-CH (CH ₃ ) ₂ , CO-NH-CH ₂ CH ₂ -C ₂ H ₅ , CO-NH-CH (CH ₃ ) -C ₂ H ₅ , CO-NH-CH ₂ -CH (CH ₃ ) ₂ or CO-NH-C (CH ₃ ) ₃ , preferably CO-NH-CH ₃ or CO-NH-C ₂ H ₅ , substituted C 1 -C ₄ -alkyl, for example for CH ₂ -CO-NH-CH ₃ , CH ₂ -CO-NH-C ₂ H ₅ , CH ₂ -CO-NH-CH ₂ -C ₂ H ₅ , CH ₂ -C0-NH-CH (CH ₃ ) ₂ , CH ₂ -CO-NH-CH ₂ CH ₂ -C ₂ H ₅ , CH ₂ -CO-NH-CH (CH ₃ ) -C ₂ H ₅ , CH ₂ -CO-NH-CH ₂ -CH (CH ₃ ) ₂ , CH ₂ -CO-NH -C (CH ₃ ) ₃ , CH (CH ₃ ) -CO-NH-CH ₃ , CH (CH ₃ ) -CO-NH-C ₂ H ₅ , 2- (CO-NH-CH ₃ ) ethyl, 2- (CO-NH-C ₂ H ₅ ) ethyl, 2- (CO-NH-CH ₂ -C ₂ H ₅ ) - ethyl, 2- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] ethyl, 2 - (CO-NH-CH ₂ CH ₂ -C ₂ H ₅ ) ethyl, 2- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] ethyl, 2- [CO-NH-CH ₂ -CH ( CH ₃ ) ₂ ] ethyl, 2- [CO-NH-C (CH ₃ ) ₃ ] ethyl, 2- (CO-NH-CH ₃ ) propyl,

2- (CO-NH-C ₂ H ₅ ) propyl, 2- (CO-NH-CH ₂ -C ₂ H ₅ ) propyl, 2- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] propyl, 2- (CO-NH-CHCH ₂ -C ₂ H ₅ ) propyl, 2- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] propyl, 2- [CO-NH-CH ₂ -CH (CH ₃ ) ₂ ] propyl, 2- [CO-NH-C (CH ₃ ) ₃ ] propyl, 3- (CO-NH-CH ₃ ) propyl,

3- (CO-NH-C ₂ H ₅ ) propyl, 3- (CO-NH-CH ₂ -C ₂ H ₅ ) propyl,

3- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] propyl, 3- (CO-NH-CH ₂ CH ₂ -C ₂ H ₅ ) propyl, 3- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] propyl, 3- [CO-NH-CH ₂ -CH (CH ₃ ) ₂ ] propyl, 3- [CO-NH-C (CH ₃ ) ₃ ] propyl, 2- (CO-NH- CH ₃ ) butyl, 2- (CO-NH-C ₂ H ₅ ) - butyl, 2- (CO-NH-CH ₂ -C ₂ H ₅ ) butyl, 2- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] butyl, 2- (CO-NH-CH ₂ CH ₂ -C ₂ H ₅ ) butyl, 2- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] butyl, 2- [CO- NH-CH ₂ -CH (CH ₃ ) ₂ ] butyl, 2- [CO-NH-C (CH ₃ ) ₃ ] butyl, 3- (CO-NH-CH ₃ ) butyl, 3- (CO-NH-C ₂ H ₅ ) butyl, 3- (CO-NH-CH ₂ -C ₂ H ₅ ) - butyl, 3- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] butyl, 3- (CO-NH- CH ₂ CH ₂ -C ₂ H ₅ ) butyl, 3- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] butyl, 3- [CO-NH-CH ₂ -CH (CH ₃ ) ₂ ] butyl .

3- [CO-NH-C (CH ₃ ) ₃ ] butyl, 4- (CO-NH-CH ₃ ) butyl, 4- (CO-NH-C ₂ H ₅ ) butyl, 4- (CO-NH-CH ₂ -C ₂ H ₅ ) butyl, 4- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] but 1,

4- (CO-NH-CH ₂ CH ₂ -C ₂ H ₅ ) butyl, 4- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] butyl, 4- [CO-NH-CH ₂ -CH (CH ₃ ) ₂ ] butyl or 4- [CO-NH-C (CH ₃ ) ₃ ] butyl, preferably for CH ₂ -CO-NH-CH ₃ CH ₂ -CO-NH-C ₂ H ₅ , CH (CH ₃ ) -CO-NH-CH ₃ or CH (CH ₃ ) -CO-NH-C ₂ H ₅ ;

Di (C 1 -C ₄ alkyl) aminocarbonyl C 1 -C ₄ alkyl for: by di (C ₄ -C ₄ alkyl) aminocarbonyl such as CO-N (CH ₃ ) ₂ , CO-N (C ₂ H ₅ ), CO-N (CH ₂ -C ₂ H ₅ ) ₂ , CO-N [CH (CH ₃ ) ₂ ] ₂ , N, N-dibutylaminocarbonyl, CO-N [CH (CH ₃ ) -C ₂ H ₅ ] ₂ , CO- [CH ₂ -CH (CH ₃ ) ₂ ] 2, CO-N [C (CH ₃ ) 3] ₂ , N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl- N- [CH (CH ₃ ) ₂ ] aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl1-N- (1-methylpropyl) aminocarbonyl, N-methyl1-N- (2-methylpropyl) aminocarbonyl, N- [C (CH ₃ ) ₃ ] -N-methylaminocarbony1, N-ethyl1-N-propylaminocarbony1, N-ethyl-N- [CH (CH ₃ ) ₂ ] - aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl- N- (1-methylpropyl) aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-ethyl-N- [C (CH ₃ ) ₃ ] aminocarbonyl, N- [CH (CH ₃ ) ₂ ] - N -propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) - N-propylaminocarbonyl, N- [C (CH ₃ ) ₃ ] -N-propylaminocarbonyl, N-butyl-N- [CH (CH ₃ ) ₂ ] aminocarbonyl, N- [CH (CH ₃ ) ₂ ] -N- (1-methylpropyl) aminocarbonyl, N- [CH (CH ₃ ) ₂ ] -N- (2-methylpropyl) aminocarbonyl, N- [C (CH ₃ ) ₃ ] -N- [CH (CH ₃ ) ₂ ] aminocarbonyl, N-butyl- N- (1-methylpropyl) aminocarbonyl, N-butyl-N- (2-methylpropyl) aminocarbonyl, N-butyl-N- [C (CH ₃ ) ₃ ] aminocarbonyl, N- (l-methylpropyl) -N- (2-methylpropyl) aminocarbonyl, N- [C (CH ₃ ) ₃ ] -N- (1-methylpropyl ) aminocarbonyl or N- [C (CH ₃ ) ₃ ] -N- (2-methylpropyl) aminocarbonyl, preferably CO-N (CH ₃ ) ₂ or CO-N (C ₂ H ₅ ) ₂ ; substituted C 1 -C ₄ alkyl, such as. B. N, N-dipropylaminocarbonylmethyl, N, N-di [CH (CH ₃ ) ₂ ] aminocarbonylmethyl, N, N-dibutylaminocarbonylmethyl, N, N-di- (1-methylpropyl) aminocarbonylmethyl, N, N-di (2-methylpropyl) aminocarbonylmethyl, N-ethyl-N-methylaminocarbonylmethyl, N-methyl-N-propylaminocarbonylmethyl, N-methyl-N- [CH (CH ₃ ) ₂ ] aminocarbonylmethyl, N-Buty1- N-methylaminocarbonylmethyl, N-methyl-N- (1-methylpropyl) aminocarbonylmethyl, 5N-methyl-N- (2-methylpropyl) aminocarbonylmethyl, N-ethyl-N-propylaminocarbonylmethyl, N-ethyl-N- [ CH (CH ₃ ) ₂ ] aminocarbonylmethyl, N-butyl-N-ethylaminocarbonylmethyl, N-ethyl-N- (1-methylpropyl) aminocarbonylmethyl, N-ethyl-N- (2-methylpropyl) aminocarbonylmethyl, N-ethyl-N - [C (CH ₃ )] aminocarbonylmethyl, N- [CH (CH ₃ ) ₂ ] -N-propylaminocarbonylmethyl, N-Buty1-N-propylaminocarbonylmethyl, N- (1-methylpropyl) -N-propylaminocarbonylmethyl, N- ( 2-methylpropyl) -N-propylaminocarbonylmethyl, N-butyl-N- (1-methylethyl) aminocarbonylmethyl, N- [CH (CH ₃ ) ₂ ] -N- (1-methylpropy1) aminocarbonylmethyl, _g N- [CH (CH ₃ ) ₂ ] -N- (2-methylpropyl) aminocarbonylmethyl, N-butyl-N- (1-methylpropyl) aminocarbonylmethyl, N-buty IN- (2-methylpropyl) aminocarbonylmethyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminocarbonylmethyl, N, N-dimethylaminocarbonylethyl, N, N-diethylaminocarbonylethyl, N, N-di (n-propy1) aminocarbonylethyl, N, N-Di- [CH (CH ₃ ) ₂ ] -aminocarbonylethyl, N, N-dibutylaminocarbonylethyl, N, N-Di (l-methylpropy1) aminocarbonylethyl, N, N-Di (2-methylpropyl) aminocarbony - ethyl, N-ethyl-N-methylaminocarbonylethyl, N-methyl-N-propyla-minocarbonylethyl, N-methyl-N- [CH (CH ₃ ) ₂ ] aminocarbonylethyl, N-butyl-N-methylaminocarbonylethyl, N-methyl-N - (1-methyl- 5 propyl) aminocarbonylethyl, N-methyl-N- (2-methylpropyl) aminocarbonylethyl, N- [C (CH ₃ ) ₃ ] -N-methylaminocarbonylethyl, N-ethyl-N-propylaminocarbonylethyl, N -Ethyl-N- [CH (CH ₃ ) ₂ ] aminocarbonyl-ethyl, N-butyl-N-ethylaminocarbonylethyl, N-ethyl-N- (1-methylpropyl) aminocarbonylethyl, N-ethyl-N- (2-methylpropyl) aminocar - 0 bonylethyl, N- [CH (CH ₃ ) ₂ ] -N-propylaminocarbonylethyl, N-Buty1- N-propylaminocarbonylethyl, N- ( 1-methylpropyl) -N-propylaminocarbonylethyl, N- (2-methylpropyl) -N-propylaminocarbonylethyl, N-butyl-N- [CH (CH ₃ ) ₂ ] aminocarbonylethyl, N- [CH (CH ₃ ) ₂ ] -N- (1-methylpropyl) aminocarbonylethyl, N- [CH (CH ₃ ) ₂ ] -N- (2-methylpropyl) ami- ^ nocarbonylethyl, N-butyl-N- (1-methylpropyl) aminocarbonylethyl, N-butyl-N- (2-methylpropyl) aminocarbonylethyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminocarbonylethyl, especially for CH ₂ CO-N (CH ₃ ) ₂ , CH ₂ CO-N (C ₂ H ₅ ) ₂ , CH ₂ CH ₂ CO-N (CH ₃ ) ₂ , CH ₂ CH ₂ CO-N (C ₂ H ₅ ) ₂ , CHCH ₃ CO-N (CH ₃ ) ₂ , CHCH ₃ CO-N (C ₂ H ₅ ) ₂ , C (CH ₃ ) ₂ C0-0 N (CH ₃ ) ₂ or C (CH ₃ ) ₂ CO-N (C ₂ H ₅ ) ₂ ;

- C 1 -C ₄ -alkoxy-C ₄ -alkoxy-Cι-C -alkyl: Cι-C -alkoxy substituted in the alkoxy part Cι-C -alkoxy-Cι-C ₄ -alkyl, for. B. -CH ₂ CH ₂ -0-CH ₂ CH ₂ -0-CH ₃ ; 5 - Cι-C -alkylthio-Cι-C -alkoxy-Cι-C alkyl: by Cι-C alkyl ₄ alkylthio in the alkoxy-substituted C ₁ -C ₄ -alkoxy-Cι-C _4, z. B. -CH ₂ CH ₂ -0-CH ₂ CH ₂ -S-CH ₃ ;

- C ₁ -C ₄ -Alkylsulfinyl-C ₁ -C ₄ -alkoxy-C-C -alkyl: C--C ₄ -alkyl-sulfinyl in the alkoxy part substituted C _! -C ₄ alkoxy -CC-alkyl, z. B. -CH ₂ CH ₂ -0-CH ₂ CH ₂ -S (0) -CH ₃ ;

-C 1 -C ₄ alkylsulfonyl -C 1 -C ₄ alkoxy-C 1 -C ₄ -alkyl: C 1 -C ₄ -alkoxy-substituted -CC ₄ -alkoxy-C 1 -C ₄ -alkyl in the alkoxy part,

For example, -CH ₂ CH ₂ -0-CH ₂ CH ₂ -S (0) ₂ -CH ₃ ;

-C 1 -C ₄ alkylamino -C ₄ -C ₄ -alkoxy-C ₄ -C ₄ -alkyl: C 1 -C ₄ -alkylamino substituted in the alkoxy part C 1 -C ₄ -alkoxy-C 1 -C ₄ -alkyl, e.g. B. -CH ₂ CH ₂ -0-CH ₂ CH ₂ -NH-CH ₃ ;

- Di (C ₁ -C ₄ -alkyl) amino-C ₁ -C ₄ -alkoxy-C ₁ -C -alkyl: C ₁ -C ₄ -alkoxyamino substituted by di-Cι-C ₄ -alkylamino in the alkoxy part -CC-C ₄ -alkoxy-C ₁ -C ₄ alkyl, e.g. B. -CH ₂ CH ₂ -0-CH ₂ CH ₂ -N (CH ₃ ) ₂ ;

- (C ₁ -C -alkoxy) carbonyl-Cι-C alkoxy-C ₁ -C ₄ alkyl: _X by C ₄ -C -A1- koxycarbonyl substituted in the alkoxy Cι-C -alkoxy-Cι-C ₄ -al - kyl, e.g. B. -CH ₂ CH ₂ -0-CH ₂ C (0) -OCH ₃ , -CH ₂ CH ₂ -0-CH (CH ₃ ) C (0) -OCH ₃ , -CH ₂ CH ₂ -0-CH ₂ C (O) -OCH ₂ CH ₃ , -CH ₂ CH ₂ -0-CH (CH ₃ ) C (O) -OCH ₂ CH ₃ ;

_(Cι-C4 alkyl) _{aminocarbonyl-Cι-C4-alkoxy-Cι-C} alkyl: by _(Cι-C4 alkyl) aminocarbonyl in the alkoxy substituted _{Cι-C4-alkoxy-Cι-C} ₄ alkyl, z. B. -CH ₂ CH ₂ -0-CH ₂ C (0) -NHCH ₃ or -CH ₂ CH ₂ -0-CH (CH ₃ ) -C (O) -NHCH ₃ ;

Di- _(Cι-C4 alkyl) _{aminocarbonyl-Cι-C4-alkoxy-Cι-C} ₄ alkyl: substituted di _(Cι-C4 alkyl) aminocarbonyl in the alkoxy C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, e.g. B. -CH ₂ CH ₂ -0-CH ₂ -C (0) -N (CH ₃ ) ₂ or -CH ₂ CH ₂ -0-CH (CH ₃ ) -C (O) -N (CH ₃ ) ₂ ;

- C ₃ -C ₄ alkenyl and the C ₃ -C ₄ alkenyl parts in C ₃ -C 4 alkenyloxy -CC-alkyl and C ₃ -C ₄ -alkenyloxycarbonyl -CC ₄ -alkyl: unsaturated, straight-chain or branched hydrocarbon radicals with 3 to 4 carbon atoms and a double bond in any position, e.g. B. 1-propenyl, 2-propenyl, 1-methylethenyl, 1-buten-1-yl, 1-buten-2-yl, 1-buten-3-yl,

2-butene-l-yl, 1-methyl-prop-l-en-l-yl, 2-methyl-prop-l-en-l-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2-en-l-yl;

- C ₃ -C ₄ -Alkynyl and the C ₃ -C ₄ -alkynyl parts in C ₃ -C ₄ -alkynyloxy- C ₁ -C ₄ -alkyl and C ₃ -C -alkynyloxycarbonyl -CC-C -alkyl: straight-chain or branched hydrocarbon groups with 3 to 4 carbon atoms and a triple bond in any Position, e.g. B. 1-propynyl, 2-propynyl (= propargyl), 1-butynyl, 2-butynyl, 3-butynyl and l-methyl-2-propynyl;

- C ₃ -C -Alkenyloxy -CC-C ₄ alkyl for: by C ₃ -C ₄ alkenyloxy such as allyloxy, but-l-en-3-yloxy, but-l-en-4-yloxy, but-2 -en-l-yloxy, l-methylprop-2-enyloxy or 2-methylprop-2-enyloxy substituted C 1 -C ₄ -alkyl, for example for allyloxymethyl, 2-allyloxyethyl or but-l-en-4-yloxymethyl, in particular for 2-allyloxyethyl;

C ₃ -C 4 alkenyloxycarbonyl-C ₁ -C ₄ alkyl for: by C ₃ -C ₄ alkenyloxycarbonyl such as allyloxycarbonyl, but-1-en-3-yloxycarbonyl, but-1-en-4-yloxycarbonyl, But-2-en-l-yloxycarbonyl, 1-methyl-prop-2-enyloxycarbonyl or 2-methylprop-2-enyloxycarbonyl-substituted C 1 -C ₄ -alkyl, for example for allyloxycarbonylmethyl, 2-allyloxycarbonylethyl or but- 1-en-4-yloxycarbonylmethyl, in particular for 2-allyloxycarbonylethyl;

C ₃ -C 4 -alkynyloxy -CC -alkyl for: by C ₃ -C ₄ -alkynyloxy such as propargyloxy, but-l-in-3-yloxy, but-l-in-4-yloxy, but-2-in -l-yloxy, l-methylprop-2-ynyloxy or 2-methylprop-2-ynyloxy, preferably propargyloxy, substituted C ₁ -C ₄ alkyl, for example for propargyloxymethyl or 2-propargyloxyethyl, in particular for 2-propargyloxyethyl;

C ₃ -C ₄ alkynyloxycarbonyl -CC-C ₄ alkyl for: by C ₃ -C ₄ -alkynyloxycarbonyl such as propargyloxycarbonyl, but-l-in-3-yloxycarbonyl, but-l-in-4-yloxycarbonyl, but -2-in-l-yloxycarbonyl, 1-methyl-prop-2-ynyloxycarbonyl or 2-methylprop-2-ynyloxycarbonyl, preferably propargyloxycarbonyl, substituted C 1 -C ₄ alkyl, for example for propargyloxycarbonylmethyl or 2-propargyloxycarbonylethyl, in particular for 2-propargyloxycarbonyl;

- C ₃ -C ₈ cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;

- C ₃ -C _B cycloalkyl -CC ₄ -alkyl: for -CC ₄ alkyl which is substituted by C ₃ -C ₈ cycloalkyl, for. B. Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cycloheptylmethyl, Cyclooctylmethyl, 2- (Cyclopropyl) ethyl, 2- (Cyclobutyl) - ethyl, 2- (Cyclopentyl) ethyl, 2- (Cyclohexyl) ethyl, 2- ( Cycloheptyl) ethyl, 2- (cyclooctyl) ethyl, 3- (cyclopropyl) propyl, 3- (cyclobutyl) propyl, 3- (cyclopentyl) propyl, 3- (cyclohexyl) propyl, 3- (cycloheptyl) propyl, 3 - (cyclooctyl) propyl, 4- (cyclopropyl) butyl, 4- (cyclobutyl) butyl, 4- (cyclopentyl) butyl,

4- (cyclohexyl) butyl, 4- (cycloheptyl) butyl, 4- (cyclooctyl) butyl; - C ₃ -C ₈ cycloalkoxy-C ₁ -C alkyl: for C ₁ -C alkyl which is substituted by C ₃ -C ₈ cycloalkoxy, e.g. B. Cyclopropoxymethyl, Cyclobutoxymethy1, Cyclopentoxy ethy1, Cyclohexyloxymethy1, Cycloheptyloxymethyl, Cyclooctyloxy ethyl, 2- (Cyclopropyl- 5 oxy) ethyl, 2- (Cyclobutyloxy) -ethyl, 2- (Cyclopentyloxy) ethyl,

2- (cyclohexyloxy) ethyl, 2- (cycloheptyloxy) ethyl, 2- (cyclooctyloxy) ethyl, 3- (cyclopropyloxy) propyl, 3- (cyclobutyloxy) propyl, 3- (cyclopentyloxy) propyl, 3- (cyclohexyloxy) - propyl, 3- (cyclo-heptyloxy) propyl, 3- (cyclooctyloxy) propyl, 4- (cyclopropyl-0 oxy) butyl, 4- (cyclobutyloxy) butyl, 4- (cyclopentyloxy) butyl,

4- (cyclohexyloxy) butyl, 4- (cycloheptyloxy) butyl, 4- (cyclooctyloxy) butyl.

Examples of N-linked 3, 4, 5, 6 or 7-membered, saturated 5 heterocyclic radicals are: aziridin-1-yl, azetidin-1-yl, pyrrolidin-1-yl, 1,3-oxazolidin-3 -yl, l, 2-oxazolidin-2-yl, tetrahydropyrazol-1-yl, piperidin-1-yl, morpholin-4-yl, hexahydropyridazin-l-yl, hexahydropyrimidin-1-yl, piperazin-1 -yl, hexahydro-1,3,5-triazin-l-yl, hexahydroazepin-1-yl, hexahydro-1,3-dia-0 zepin-1-yl and hexahydro-1,4-diazepin-l- yl.

With regard to the use of the compounds of the formula I as herbicides or for the desiccation and / or defoliation of plants, it has proven to be advantageous if the variables X, R ¹ and R ² ₅ in formula I alone or in combination have the following meanings exhibit:

X chlorine or bromine, especially chlorine;

_Q R ^{1 is} hydrogen or in particular methyl;

R ^{2 has} one of the abovementioned meanings, in particular an OR ^{3 group} , in which R ^{3 has} the abovementioned meanings, preferably different from hydrogen. 5

In group OR ³ , R ³ preferably has the following meanings:

R ^{3 is} hydrogen, Cη-C ₄ -alkyl, -C-C ₄ -haloalkyl, hydroxy-Cι-C ₄ -alkyl, amino-Cι-C ₄ -alkyl, Cι-C ₄ -cyanoalkyl, C _! -C ₄ -alkoxy-Cι-C ₄ - 0 alkyl, C ₁ -C ₄ -alkylthio-Cι-C ₄ -alkyl, C ₁ -C ₄ -alkyl-C ₁ -C ₄ -sulfonyl- Cι-C ₄ - alkyl, C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylamino -C-C -alkyl, di-Cι-C ₄ -alkylamino-Cι-C ₄ -alkyl, Cι- C -alkyloxy-carbonyl-C _! -C ₄ -alkyl, aminocarbonyl-C ₁ -C -alkyl, -C-C ₄ -alkyl-minocarbonyl-Cι-C ₄ -alkyl, di-Cι-C4-alkylaminocarbonyl-Cι-C ₄ - ₅ alkyl, Cι-C ₄ -Halogenalkoxy-C ₁ -C ₄ alkyl, aminocarbonyl -CC-alkoxy-Cι-C -alkyl, C ₁ -C ₄ -cyanoalkoxy-C ₁ -C ₄ -alkyl, Cι-C ₄ -alkoxy- xy -C-C -alkoxy-Cι-C -alkyl, C ₁ -C ₄ -alkylthio-Cι-C ₄ -alko- xy -CC ₄ -alkyl, -CC ₄ -alkyl-C ₁ -C ₄ -sulfonyl -CC-C ₄ -alkoxy-C ₁ -C ₄ -alkyl, -C-C ₄ -alkylaminocarbonyl -CC-C- alkoxy-Cι-C alkyl, di- C ₁ -C ₄ alkylaminocarbonyl-Cι-C ₄ -alkoxy-C ₁ -C ₄ alkyl, C ₃ -C alkenyl-nyl, _C3-alkynyl, C ₃ -C -Alkenyloxy-C ₁ -C ₄ -alkyl, C ₃ -C-alkynyloxy-Cι-C -alkyl, C ₃ -C -Alkenyloxycarbonyl-Cι-C ₄ -alkyl, C ₃ -C - alkynyloxycarbonyl- C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl-C ₄ -C ₄ -alkyl. Examples of preferred meanings of OR ³ are the meanings given below in Table 1, lines 3 to 47.

In particular R ³ is Cι-C -alkyl, C haloalkyl, _Cι-C4 - cyanoalkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ alkyl, C ₁ -C alkylthio-C ₁ - C ₄ alkyl, -CC ₄ alkyloxycarbonyl -CC ₄ alkyl, C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl.

If R ^{2 represents} a group of the general formula NRR ⁵ , then preferably mean:

R ^{4 is} hydrogen, -CC ₄ alkyl, C _! -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, _{Cι-C4-alkoxy-Cι-C} alkyl, or C ₁ -C alkyloxycarbonyl-C ₁ -C -AL- alkyl and

R ^{5 is} hydrogen or -CC ₄ alkyl, especially hydrogen or methyl; or R ⁴ and R ⁵ together with the nitrogen atom to which they are attached form a saturated 5 or

6-membered heterocyclic radical, which optionally has a further oxygen atom and / or an imino or -CC ₄ -alkyl limino group as a ring member, for example a pyrrolidinyl, piperidinyl, piperazinyl, or morpholinyl radical.

Examples of preferred groups of the general formula NR ⁴ R ⁵ are the meanings given in Table 1, lines 48 to 58 for R ² .

Compounds of the general formula I in which X and R ^{1 have} the abovementioned meanings, in particular those which are mentioned as preferred, and in which R ^{2 represents} chlorine, C 1 -C ₄ -alkoxy or OH are also intermediates for the preparation of other compounds Formula I of particular interest.

Examples of particularly preferred compounds of the general formula I are the compounds of the general formula Ia given below (compounds I in which R ^{1 is} CH ₃ and X are Cl) in which R ^{2 is} that in lines 1 to 58 of Table 1 has the meanings given. These compounds are also referred to below as compounds Ia.l to Ia.58.

Examples of particularly preferred compounds of the general formula I are furthermore the compounds of the general formula Ib given below, in which R ^{1 is} H and X is Cl and R ^{2 has} the meanings given in rows 1 to 58 of table 1 has (compounds Ib.l to Ib.58).

Examples of particularly preferred compounds of the general formula I are furthermore the compounds of the general formula Ic given below, in which R ^{1 represents} CH ₃ and X represents Br and R ^{2 has} the meanings given in rows 1 to 58 of Table 1 (Compounds Ic.l to Ic.58).

Further examples of particularly preferred compounds of the general formula I are the compounds of the general formula Id given below, in which R ^{1 is} H and X is Br and R ^{2 has} the meanings given in rows 1 to 58 of Table 1 ( Connections Id.l to Id.58).

The compounds of the formula I can be prepared in accordance with WO 97/07104 or WO 99/52878 by first of all an aniline derivative of the formula III into a hydrazine of the formula Ha (compounds of the formula II with R ^a = R ^b = H), this is then converted with the ketone of the formula F ₃ CC (0) -CHBr (trifluorodibromoacetone) or another equivalent of the 2-oxo-3-trifluoropropanal to a hydrazone of the general formula IIb (compounds II, in which R ^a and R ^{b form} a group of the formula = CH-C (0) -CF ₃ ) condenses and the compound Ilb is then reacted with a phosphorus compound of the formula IV in the sense of a Wittig reaction with subsequent ring closure to give a pyridazinone of the formula I. In formula IV, the radical R is usually a Cη-C ₄ alkyl group, for. B. for ethyl. In Scheme 1, the variables X and R ^{2 have} the meanings mentioned above. In a preferred embodiment of the process shown in scheme 1, R ^{2 represents} a group OR ³ with R ³ ≠-H and in particular C 1 -C ₄ alkoxy.

Scheme 1:

F ₃ CC (0) -CHBr ₂ (Ha)

R ^l (Ilb)

I

(C ₆ H ₅ ) ₃ P = CC (0) OR (IV)

The 3-aminocinnamic acid compounds of the formula III are partly. known from the literature, for example from EP-A 240 659, EP-A 300 387 and DE-A 39 04 082, or can be prepared analogously to the methods described there.

The 3-aminocinnamic acid compound III can be converted into the corresponding hydrazine compound Ha by the methods known for converting aniline compounds into aromatic hydrazines (see, for example, Houben-Weyl Volume EI, nitrogen compounds I, Georg Thieme Verlag 1967). Typical processes include the diazotization of the amino group in III, for example by reacting III with nitrite salts such as sodium nitrite in the presence of mineral acids e.g. B. by reaction in concentrated hydrochloric acid, and then reducing the resulting diazonium compounds, eg. B. with tin (II) chloride under acidic reaction conditions. The hydrazones of the formula IIb can be prepared, for example, by reacting the hydrazine Ha with a derivative of 2-0xo-3-trifluoropropanal such as trifluorodibromoacetone using the methods described in WO 97/07104 and WO 99/52878. Derivatives of 2-oxo-3-trifluoropropanal such as trifluorodibromoacetone (CAS No. 431-67-4) are in part commercially available or can be prepared by processes known from the literature.

I is prepared by reacting compound IIb with a compound IV in the sense of a Wittig or Wittig-Horn reaction under the reaction conditions customary for this, as described, for example, in WO 97/07104 or DE-A 197 54 348 are described. The required phosphorus compounds of the formula IV are known from the literature or can be prepared by known processes in the literature. Some of them are commercially available, e.g. B. (1-Ethoxycarbonylethylidene) triphenylphosphorane (CAS No. 5717-37-3).

It has also been found that compounds of the formula I in which R ^{2 represents} an OR ³ radical having the meanings given for R ³ , for example C 1 -C ₄ -alkyl, according to scheme 2 below, in other compounds of the general formula I can be converted. In scheme 2, R ^2a in formula I 'thus represents OR ³ with the meanings given above for R ^3, for example with R ³ = C 1 -C ₄ -alkyl. Compounds I 'with R ^2a = OR ³ = 0 -CC-C ₄ alkyl are also referred to below as lower alkyl esters I.

For this purpose, compounds of the formula I 'are saponified according to scheme 2 to give the free acid of the formula I "(R ² = OH) and, preferably after activation, for example to give the acid chloride (compounds of the formula I with R ² = Cl), with another alcohol ³ or an amine HNR ⁴ R ⁵ to a compound I in the form of an ester derivative (R ² = OR ³ ) or an amide derivative (R ² = NR ⁴ R ⁵ ). Here and below, the variables R ³ - R ^{5 has} the meanings mentioned above. For saponification, for example, the ester I ', preferably a lower alkyl ester I' (R ^2a = 0 -CC-C-alkyl), is introduced in a mixture of acid, water and, if appropriate, a solvent. If necessary, the saponification is carried out with heating.

Suitable acids are mineral acids such as hydrochloric acid, hydrobromic acid, sulfuric acid or phosphoric acid and trifluoroacetic acid, which are generally used as aqueous acids (concentration, for example, 5 to 98% by weight). In addition to water, organic carboxylic acids such as acetic acid are preferred as solvents.

A mixture of aqueous acid and solvent is usually used, the volume ratio of aqueous acid and solvent generally being from 1:99 to 99: 1, and preferably in the range from 1: 4 to 4: 1. The reaction temperatures required for saponification are generally in the range from 20 to 160 ° C., but preferably from 20 to 120 ° C.

All common activation methods are suitable for activating the acid I ", for example conversion into the acid chloride, activation with carbodiimides such as dicyclohexylcarbodiimide or, when I" is reacted with alcohols HÖR ^3, the classic proton catalysis with mineral acids such as sulfuric acid.

The activation is preferably carried out by converting I "to the acid chloride of the formula I (R ² = Cl), which is typically carried out using thionyl chloride, oxalyl chloride or PC1 ₃ or PCI ₅ as the chlorinating agent. Inert solvents such as methylene chloride, chloroform are used here as solvents , Dichloromethane or toluene. However, the reaction can also be carried out in the chlorinating agent itself as a solvent or in the melt. Depending on the chlorinating agent, one works with 1 to 5 equivalents of the chlorinating agent (or with a large excess if the chlorinating agent serves as solvent ) and at temperatures between -78 ° C and 150 ° C.

The further reaction of the acid chloride I (R ² = Cl) with the alcohol HÖR ³ or the amine HNR ⁴ R ⁵ is usually also carried out in an inert solvent such as methylene chloride, chloroform,

Dichloroethane or toluene. For this purpose, 1 to 5 equivalents of the alcohol HÖR ³ or amine HNR ⁴ R ⁵ , based on the acid chloride, are preferably used. If appropriate, the reaction is carried out with the addition of preferably 1 to 5 equivalents of an auxiliary base, for. B. a trialkylamine such as triethylamine or pyridine. The reaction is preferably carried out at temperatures in the range from 0 ° C. to 100 ° C.

A further advantageous embodiment of this reaction consists in introducing the acid I "in the alcohol HÖR ³ intended for esterification or a mixture of this alcohol with one of the solvents mentioned above and reacting it in situ with thionyl chloride.

A further advantageous embodiment of the reaction consists of introducing the acid I "in the alcohol HÖR ³ intended for esterification or a mixture of this alcohol with one of the abovementioned solvents as a solvent and reacting it in the presence of a catalytic amount of a mineral acid such as sulfuric acid The amount of mineral acid is between 1 and 100 mol%, based on the acid I (R ² = OH).

The 2-phenyl-2H-pyridazin-3-ones according to the invention of the general formula I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides. The compounds I or their herbicidal compositions comprising salts control vegetation very well on non-cultivated areas, particularly at high application rates. In crops such as wheat, rice, maize, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.

Furthermore, the 2-phenyl-2H-pyridazin-3-ones according to the invention of the general formula I and their agriculturally useful salts are also suitable for the desiccation and / or defoliation of plants.

As desiccants, they are particularly suitable for drying out the aerial parts of crops such as potatoes, rapeseed, sunflower and soybeans. In this way a completely mechanical harvesting of these important crop plants is made possible.

Also of economic interest is the time-controlled dropping of fruits or the reduction of their adherence to the plant, for example in the case of citrus fruits, olives and other types of pome, stone and shell fruit, since this makes harvesting these fruits easier. The fall-off is based on the formation of separating tissue between the fruit, leaf and shoot part of the plants and is caused by the 2-phenyl-2H-pyridazin-3-ones according to the invention of the general formula I and their Promoted salts. The use of the 2-phenyl-2H-pyridazin-3-ones according to the invention of the general formula I and their agriculturally useful salts thus permits controlled dropping of fruits or controlled defoliation of the crop plant (defoliation) and thus enables one in crops of this type facilitate harvesting. Controlled defoliation is also of particular interest for crops such as cotton. The shortening of the time interval in which the individual cotton plants ripen thereby achieves an increased quality of the harvested fiber material.

Depending on the particular application method, the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants. The following crops are considered, for example:

Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica,

Brassica rapa var. Silvestris, Camellia sinensis, Carthamus tincorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Cof- fea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaaria guineens sca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Lyum maniconisissimum, Linum usicon spec esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communisis, Ribes sylvestre , Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vini fera, zea mays.

In addition, the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.

The application of the herbicidal compositions or the active compounds which contain the 2-phenyl-2H-pyridazin-3-ones of the general formula I and / or their salts can be carried out pre-emergence, post-emergence or together with the seed of a crop respectively. There is also the possibility of applying the herbicidal compositions or active compounds by using the herbicidal compositions or active ingredients pretreated seeds of a crop are applied. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit wherever possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).

The compounds of the formula I according to the invention or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents or Granules can be applied by spraying, atomizing, dusting, scattering, pouring or treating the seed or mixing with the seed. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention. The agents according to the invention generally contain a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and the auxiliaries customary for the formulation of crop protection agents.

Inert additives are essentially: mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, eg. B. amines such as N-methylpyrrolidone or water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds I as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, concentrates consisting of an active substance, wetting agent, adhesive, dispersant or emulsifier and possibly solvent or oil can also be prepared which are suitable for dilution with water. As surface-active substances come the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. B. lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, Polyoxyethylenoc- octylphenol ether, ethoxylated isooctyl- ralkohole, octyl- or nonylphenol, alkylphenyl, tributylphenyl, Alkylarylpolyethe-, isotridecyl alcohol, fatty alcohol condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxy - Propylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite waste liquor or methyl cellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

Granules, e.g. B. coating, impregnation and homogeneous granules can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.

The concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range. The formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The compounds I according to the invention can be formulated, for example, as follows:

I 20 parts by weight of compound no. Ia.3 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulene. fonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By

d?

»

VIII 1 part by weight of compound no. 51 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (non-ionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained.

To broaden the spectrum of activity and to achieve synergistic effects, the compounds of the general formula I according to the invention can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acids and their derivatives, aminotriazoles, anilides, (het) -aryloxyalkanoic acid and their derivatives, benzoic acid and their derivatives, benzothiadiazinones come as mixing partners , 2-Aroyl-l, 3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF ₃ phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclohexane-l, 3-dione derivatives, diazines, dichloropropionic acid Derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5, 6-tetrahydrophthalimides , Oxadiazoles, oxiranes, phenols, aryloxy- or heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acids and their derivatives, Py rimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uraciles.

It can also be useful to apply the compounds I alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.

Depending on the control target, the season, the target plants and the growth stage, the active compound application rates are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (see also).

The following examples are intended to illustrate the invention:

The following abbreviations have been used: s = singlet d = doublet t = triplet q = quartet m = multiplet br = broad signal.

All signals are given as chemical shifts in ppm against tetraethylsilane (TMS). The number of hydrogen atoms to be assigned to the signal is also given.

I Manufacturing examples:

Example 1: 2- [4-chloro-3- (2-ethoxycarbonyl-2-chloroethen-l-yl) phenyl] -4-methyl-5-trifluoromethyl-2H-pyridazin-3-one

(Connection Ia.4)

1.1 4-Chloro-3- (2-ethoxycarbonyl-2-chloroethen-l-yl) phenylhydrazine

5.0 g (0.019 mol) of 4-chloro-3- (2-ethoxycarbonyl-2-chloroethen-l-yl) aniline were placed in 100 ml of concentrated hydrochloric acid and at 0 to 5 ° C with 1.5 g (0, 02 mol) sodium nitrite, dissolved in 15 ml water, added dropwise. After a further 1 h at 0 to 5 ° C., the reaction mixture was added to a solution of 10.8 g (0.048 mol) of tin (II) chloride hydrate in 100 ml of concentrated hydrochloric acid and the mixture was stirred at 0 to 5 ° C. for 3 h. The mixture thus obtained was poured onto ice water, adjusted to pH 12 with 50% strength by weight aqueous sodium hydroxide solution and the precipitated product was filtered off. After washing and drying, 3.1 g of 4-chloro-3- (2-ethoxycarbonyl-2-chloroethen-1-yl) phenylhydrazine (compound Ila.l) remained.

* H NMR (D ₆ -DMSO): 8.1 (s, IH), 7.4 (s, 1 H), 7.3 (d, 1 H), 7.1 (s, 1 H), 6.9 (d, 1 H), 4.4 (q, 2 H), 4.2 (br, 2 H), 1.3 (t, 3 H)

1.2 4-chloro-3- (2'-ethoxycarbonyl-2'-chloroethen-1-yl) phenylhydrazone of 3, 3, 3-trifluoro-2-oxopropanal (compound Ilb.l)

2.3 g (0.028 mol) of sodium acetate were dissolved in 43 ml of water and 3.3 g (0.0124 mol) of trifluorodibromoacetone were added dropwise. After 20 min at 70 ° C., the mixture was cooled to room temperature and a solution of 3.1 g (0.012 mol) of the hydrazine Ila.l in 110 ml of diethyl ether was added dropwise. The mixture was stirred overnight at room temperature, the organic phase was separated off and extracted the aqueous phase with 100 ml of diethyl ether. Evaporation of the combined organic phases gave the title compound Ilb.l (4.0 g). Fixed point 164-167 ° C.

² H NMR (D ₆ -DMSO): 8.1 (s, IH), 7.9 (d, 1 H), 7.6 (d, 1 H), 7.5 (m, 1 H), 7.1 (m, 1 H), 4.2 (q, 2 H), 1.3 (t, 3 H)

1.3 2- [4-chloro-3- (2-ethoxycarbonyl-2-chloroethen-l-yl) -phenyl] -4-methyl-5-trifluoromethyl-2H-pyridazin-3-one (compound la.4)

4.0 g (0.01 mol) of the hydrazone Ilb.l were dissolved in 30 ml of tetrahydrofuran (THF). To this was added 4.0 g (0.01 mol) of (l-ethoxycarbonylethylidene) triphenylphosphorane. After 3 h at reflux, the mixture was washed with DMF / H ₂ 0, the organic phase was concentrated and the solid residue was chromatographed (cyclohexane / ethyl acetate). Compound Ia.4 was obtained in a yield of 1.0 g.

! H NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.1 (s, 1 H), 8.0 (d, 1 H), 7.7 (m, 1 H), 7.6 (m, 1 H), 4.4 (q. 2 H), 2.5 (t, 3 H), 1.4 (t, 3 H).

Example 2: 2- [4-chloro-3- (2-hydroxycarbonyl-2-chloroethen-l-yl) phenyl] -4-methyl-5-trifluoromethyl-2H-pyridazin-3-one

(Connection Ia.l)

0.5 g (0.0012 mol) of the pyridazinone Ia.4 from Example 1 was stirred in 16 ml of a 1: 1 (v / v) mixture of concentrated hydrochloric acid and glacial acetic acid at 80 ° C. for 4 h and cooled. The title compound (acid Ia.l) precipitated out as a solid, which was filtered off with suction. Yield: 0.3 g. Fixed point 168 ° C.

^l E NMR (De-DMSO): 8.3 (s, IH), 8.2 (d, 1 H), 7.8-7.6 (m, 2 H), 2.3 (t, 3 H)

Example 3: 2- [4-chloro-3- (2-chlorocarbonyl-2-chloroethen-l-yl) phenyl] -4-methyl-5-trifluoromethyl-2H-pyridazin-3-one (compound Ia.2)

0.3 g (0.76 mmol) of acid Ia.l from Example 2 were refluxed in 10 ml of thionyl chloride for 3 h and then the ionyl chloride was removed in vacuo. The acid chloride Ia.2 obtained in the reaction was directly reacted further. Example 4: 2- [4-chloro-3- (2-methoxycarbonyl-2-chloroethen-l-yl) phenyl] -4-methyl-5-trifluoromethyl-2H-pyridazin-3-one (compound Ia.3)

0.03 g of methanol were placed in 0.07 g of pyridine together with a catalytic amount of 4-dimethylaminopyridine in 10 ml of methylene chloride, and the acid chloride (compound la.2), dissolved in 10 ml of methylene chloride, was added dropwise. The mixture was stirred until a thin-layer chromatogram (silica gel, cyclohexane / ethyl acetate) showed no further change. The solution was concentrated in vacuo and the residue was chromatographed on silica gel (cyclohexane / ethyl acetate). Compound Ia.3 was thus obtained in a yield of 0.24 g. Fixed point 80-81 ° C.

! H NMR (CDC1 ₃ ): 8.3 (d, IH), 8.1 (s, IH), 8.0 (s, IH), 7.7 (m, IH), 7.6 (m, IH), 4.0 (s.3 H ), 2.4 (t, 3H).

Example 5: 2- {4-chloro-3- [2- (2-chloroethoxy) carbonyl-2'-chloroethen-l-yl] phenyl} -4-methyl-5-trifluoromethyl-2H-pyridazine -3-on (connection Ia.8)

Analogously to the procedure described in Examples 3 and 4, 0.5 g of acid from Example 2 (compound Ia.l) was first converted to acid chloride Ia.2 and then with 0.12 g of 2-chloroethanol. 0.35 g of 2-chloroethyl ester Ia.8 was obtained. Fixed point 75-76 ° C.

iH-NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.1 (s, 1 H), 8.0 (s, 1 H), 7.7 (m, 1 H), 7.6 (m, 1 H), 4.6 ( m. 2 H), 3.8 (m, 2 H), 2.4 (t, 3 H).

Examples 6 to 11

Analogously to the procedure described in Examples 3 and 4, the compounds specified below were obtained by reacting the acid Ia.l from Example 2 to the acid chloride Ia.2 and then reacting with the respective alcohol.

Example 6: 2- {4-chloro-3- [2- (2-methoxyethoxy) carbonyl-2-chloroethen-l-yl] phenyl} -4-methyl-5-trifluoromethyl-2H-pyridazine- 3-one (connection Ia.12)

Fixed point 60-62 ° C. ! H NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.1 (s, 1 H), 8.0 (s, 1 H), 7.7 (m, 1 H), 7.6 (m, 1 H), 4.5 (. 2 H), 3.7 (m, 2 H), 3.4 (s, 3H) 2.4 (t, 3 H).

Example 7: 2- {4-chloro-3- [2- (2-cyanoethoxy) carbonyl-2-chloroethen-1-yl] phenyl} -4-methyl-5-trifluoromethyl-2H-pyridazine- 3-one (connection Ia.16)

Fixed point 78-79 ° C.

iH-NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.1 (s, 1 H), 8.0 (s, 1 H), 7.7 (m, 1 H), 7.6 (m, 1 H), 4.5 ( m. 2 H), 2.9 (m, 2 H), 2.4 (t, 3 H).

Example 8: 2- {4-chloro-3- [2- (2-methylthioethoxy) carbonyl-2-chloroethen-l-yl] phenyl} -4-methyl-5-trifluoromethyl-2H-pyridazine- 3-one (connection Ia.17)

oil

! H NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.1 (s, 1 H), 8.0 (s, 1 H), 7.7 (m, 1 H), 7.6 (m, 1 H), 4.5 (m. 2 H), 2.9 (m, 2 H), 2.4 (t, 3 H), 2.2 (s, 3 H).

Example 9: 2- {4-Chloro-3- [2- (ethoxycarbonyl) methoxycarbonyl-2-chloroethen-l-yl] phenyl} -4-methyl-5-trifluoromethyl-2H-pyridazin-3- on (connection Ia.24)

oil

! H NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.1 (s, 1 H), 8.0 (d, 1 H), 7.7 (m, 1 H), 7.6 (m, 1 H), 4.8 (s, 2 H), 4.3 (q. 2 H), 2.5 (t, 3 H), 1.3 (t, 3 H).

Example 10: 2- [4-chloro-3- (2-allyloxycarbonyl-2-chloroethen-l-yl) phenyl] -4-methyl-5-trifluoromethyl-2H-pyridazin-3-one (compound Ia.41)

Fixed point: 62-63 ° C

! H NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.1 (s, 1 H), 8.0 (s, 1 H), 7.7 (m, 1 H), 7.6 (m, 1 H), 6.0 (m. 1 H), 5.5-5.3 (2 x dd, 2 H), 4.8 (d, 2H), 2.4 (t, 3 H). Example 11: 2- [4-chloro-3- (2-propargyloxycarbonyl-2-chloroethen-1-yl) phenyl] -4-methyl-5-trifluoromethyl-2H-pyridazin-3-one (compound Ia.42)

Fixed point: 81-82 ° C

iH-NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.1 (s, 1 H), 8.0 (s, 1 H), 7.7 (m, 1 H), 7.6 (m, 1 H), 5.9 ( d. 2 H), 2.6 (t, 1 H), 2.4 (t, 3 H).

Example 12: 2- [4-chloro-3- {2- (pyrrolidin-1-ylcarbonyl} -2-chloroethen-1-yl) phenyl] -4-methyl-5-trifluoromethyl-2H-pyridazine -3-on (connection Ia.51)

The acid chloride Ia.2 was prepared from 0.8 g of acid Ia.l in the manner described in Example 2, which was then reacted without further purification with 0.16 g of pyrrolidine in 20 ml of dichloromethane in the presence of catalytic amounts of dimethylaminopyridine , The solution was concentrated in vacuo and the residue was chromatographed on silica gel (cyclohexane / ethyl acetate). Compound la.51 was thus obtained in a yield of 1.04 g. Oil.

! H NMR (CDC1 ₃ ): 8.2 (d, 1 H), 8.0 (s, 1 H), 7.6 (m, 1 H), 7.5 (m, 1 H), 7.1 (s, 2 H), 3.6 (m, 4H), 2.4 (t, 3H), 2.0 (m, 4H).

Example 13: 2- [4-chloro-3- {2- (N- (ethoxycarbonylmethyl) methylamino-carbonyl} -2-chloroethen-l-yl) phenyl] -4-methyl-5-trifluoromethyl-2H- pyridazin-3-one (compound Ia.55)

Compound Ia.55 was prepared in the manner described in Example 12 by reacting the acid chloride Ia.2 with N-methylglycethyl ester. Oil (mixture of rotamers).

! H NMR (CDC1 ₃ ): 8.1 (2 br. S *, 1 H), 8.0 (s, 1 H), 7.6 (m, 1 H), 7.5 (m, 1 H), 7.2 (br., 2 H), 4.2 (m, 5 H), 3.3-3.1 (2.br. S *, 3H), 2.4 (t, 3 H), 2.0 (m, 4 H). * two signals due to two rotamers

Example 14: 2- [4-chloro-3- (2-ethoxycarbonyl-2-chloroethen-l-yl) phenyl] -5-trifluoromethyl-2H-pyridazin-3-one (compound Ib.4)

5.0 g of the hydrazone Ilb.l were reacted with 4.5 g (1-ethoxycarbonylmethylidene) triphenylphosphorane according to the procedure given in Example 1.3. After working up in the there described compound Ib.4 was obtained in a yield of 3.5 g. Fixed point: 98-100 ° C

1 H NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.1 (s, 1 H), 8.0 (d, 1 H), 7.7 (m, 1 H), 7.6 (m, 1 H), 7.3 ( t, 1 H), 4.4 (q. 2 H), 1.4 (t, 3 H).

Example 15: 2- [4-chloro-3- (2-methoxycarbonyl-2-chloroethen-l-yl) phenyl] -5-trifluoromethylpyridazin-3-one (compound Ib.3)

The title compound Ib.3 was prepared starting from compound Ib.4 from Example 14 analogously to the route shown in Examples 2 to 4. Fixed point: 140-141 ° C

iH-NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.2 (s, 1 H), 8.1 (m, 1 H), 7.7-7.6 (m, 2 H), 7.3 (m, 1 H), 3.9 (s, 3H).

Example 16: 2- [4-chloro-3- (2- (2'-chloroethyloxy) carbonyl-2-chloroethen-1-yl) phenyl] -5-trifluoromethylpyridazin-3-one (Compound Ib.8)

The title compound Ib.8 was prepared starting from compound Ib.4 from Example 14 analogously to the route shown in Examples 2, 3 and 5. Fixed point: 94-95 ° C

iH-NMR (CDC1 ₃ ): 8.3 (d, 1 H), 8.2 (s, 1 H), 8.1 (d, 1 H), 7.7-7.4 (m, 2 H), 7.3 (m, 1 H), 4.6 (m, 3H), 3.8 (m, 3H).

Table 2 shows the compounds of Examples 1 to 16. All of the compounds listed in Table 2 are at least 95% Z-isomers.

Table 2

^χ ) see table 1

II Examples of use

II.1 Herbicidal action

The herbicidal activity of the 2-phenylpyridazin-3-one compounds of the formula I was demonstrated by greenhouse tests:

Plastic pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to species.

In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles. The tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, unless this was affected by the active ingredients.

For the purpose of post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the growth habit, and then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment. The application rate for post-emergence treatment was 15.6 and 7.8 g aS / ha. The plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species. The trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.

Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.

The plants used in the greenhouse experiments are composed of the following types:

The compound Ia.4 from Example 1 and the compound of Example 1-637 (X = H) known from WO 97/07104 were tested in the manner described in the post-process. The results are summarized in Table 3:

Table 3

The values in Table 3 clearly show the advantages of the compound according to the invention.

II.2 Effect as desiccants / defolianties

Young, 4-leafed (calculated without cotyledons) cotton plants served as test plants were grown under greenhouse conditions (relative humidity 50-70%, day / night temperature 27 or 20 ° C).

The young cotton plants were treated to runoff with an aqueous preparation of the respective active ingredient, which additionally contained 0.15% by weight, based on the total weight of the preparation, of a fatty alcohol ethoxylate (Plurafac® LF 700). The amount of water applied was about 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation were determined. The untreated control plants showed no defoliation.

Claims

claims

2-phenyl-2H-pyridazin-3-one compounds of the general formula I

where the variables R ¹ , R ² and X have the following meanings:

X halogen;

R ^{1 is} hydrogen or -CC ₄ alkyl;

R ^{2 is} chlorine, OR ³ or NR ⁴ R ⁵ , wherein

R ³ , R ⁴ independently of one another hydrogen, -CC alkyl, -C-haloalkyl, hydroxy-Cχ-C alkyl, -C-alkoxy-Cι-C ₄ alkyl, cyano-Cι-C ₄ alkyl , -CC ₄ -alkylthio -CC ₄ -alkyl,

C ₁ -C alkylsulfinyl -CC -alkyl,

C 1 -C ₄ alkylsulfonyl C 1 -C ₄ alkyl, amino C 1 -C ₄ alkyl,

C 1 -C ₄ alkylamino C 1 -C ₄ alkyl,

Di- (-C ₄ -alkyl) amino -CC-C -alkyl, hydroxycarbonyl -CC-C -alkyl,

(-CC ₄ alkoxy) carbonyl -CC ₄ alkyl,

C 1 -C ₄ haloalkyloxycarbonyl C 1 -C ₄ alkyl,

Aminocarbonyl -CC-alkyl,

(-C 1 -C ₄ -alkyl) aminocarbonyl-C 1 -C ₄ -alkyl, di- (Cχ-C -alkyl) aminocarbonyl-C 1 -C 4 -alkyl,

-C-C ₄ -haloalkoxy-C ₁ -C -alkyl, hydroxy-Cι-C-alkoxy-Cι-C ₄ -alkyl, -C-C-alkoxy-Cι-C -alkoxy-Cι-C ₄ -alkyl, cyano- _{Cι-C4-alkoxy-Cι-C} ₄ alkyl, C ₁ -C ₄ _{-alkylthio-Cι-C4-alkoxy-Cι-C} ₄ alkyl,

Cι-C-alkylsulfinyl-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C _{alkylsulfonyl-Cι-C4-alkoxy-Cι-C} ₄ alkyl, amino-Cι-C ₄ alkoxy -C-C ₄ -alkyl, -C-C-alkylamino-Cι-C ₄ -alkoxy-Cι-C ₄ -alkyl, Di- (-C-C ₄ alkyl) amino-C ₁ -C -alkoxy-C ₁ -C ₄ -alkyl, hydroxycarbonyl-C -C -alkoxy-Cι-C ₄ -alkyl, (Cχ-C -alkoxy) carbonyl -Cι-C-alkoxy-C _! -C -alkyl, aminocarbonyl -CC -alkoxy-Cι-C -alkyl, (-C -C-alkyl) aminocarbonyl-Calk-C -alkoxy-Cι-C -alkyl,

Di- (C ₁ -C ₄ alkyl) aminocarbonyl-C ₁ -C ₄ alkoxy-C ₁ -C alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C alkenyloxy -C-C ₄ -alkyl, C ₃ -C ₄ -alkynyloxy-Cι-C -alkyl, C ₃ -C ₄ -alkenyloxycarbonyl-Cι-C ₄ -alkyl,

C ₃ -C ₄ alkynyloxycarbonyl -CC-alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₈ -cycloalkyl-Cι-C ₄ -alkyl, C ₃ -C ₈ -cycloalkoxy -CC-C ₄ - alkyl; and

R ⁵ is hydrogen, C ₁ -C ₄ -alkyl, C ₄ alkoxy, C ₃ -C ₆ alkenyl,

C ₃ -C alkenyloxy, C -C ₆ alkynyl, C ₃ -C ₄ alkynyloxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₈ mean cycloalkyl -CC -alkoxy;

R ⁴ and R ⁵ together with the nitrogen atom to which they are attached can also represent a saturated or unsaturated 3, 4, 5, 6 or 7-membered heterocyclic radical, the 1 or 2 further heteroatoms selected from oxygen and sulfur , and / or one or two imino or -CC alkylimino groups as ring members and / or one or two substituents selected from halogen, -CC alkyl and -C-alkoxy may have;

and the agriculturally useful salts of compounds of the formula I.

2. Compounds according to claim 1 of the general formula I, wherein R ^{2 represents} a group OR ³ .

3. Compounds according to claim 1 or 2 of the general formula I, wherein R ^{1 is} methyl.

4. Compounds according to any one of claims 1 to 3 of the general formula I, wherein X represents chlorine or bromine.

5. Diazinyl cinnamic acid compounds of the general formula II

wherein

R ^a and R ^{b are} simultaneously hydrogen or form a group = CH-C (0) -CF ₃

and the variables R ² , R ³ and X have the meanings given in claim 1.

6. Use of 2-phenyl-2H-pyridazin-3-one compounds of the general formula I and their agriculturally useful salts, according to claim 1, as herbicides or for desiccation / defoliation of plants.

7. A composition comprising a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I as claimed in claim 1 and at least one inert liquid and / or solid carrier and, if desired, at least one surface-active substance.

8. Agent for the desiccation and / or defoliation of plants, containing a desiccant and / or defoliantly effective amount of at least one compound of formula I or an agriculturally useful salt of I, according to claim 1, and at least one inert liquid and / or solid carrier and if desired, at least one surfactant.

9. A method for controlling undesirable plant growth, characterized in that a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, according to claim 1, is allowed to act on plants, their habitat or on seeds.

10. A process for the desiccation and / or defoliation of plants, characterized in that a desiccant and / or defoliantly effective amount of at least one compound of the formula I or an agriculturally useful salt of I, according to claim 1, is allowed to act on plants.