DD261734A5 - PROCESS FOR PROTECTING CULTURAL PLANTS - Google Patents

Abstract

The invention relates to a method of protecting crop plants using quinoline derivatives against the deleterious effects of herbicidally active 2- & 4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy! -Propionic acid derivatives and herbicidal compositions which comprise a combination of herbicide and protective quinoline derivative. The invention provides a novel method of protecting crops when herbicides are applied to a crop culture for weed control purposes. The object of the invention is to provide especially suitable active ingredients for protecting the crop plants from the phytotoxic effects of said herbicide class. According to the invention, a method for protecting crop plants against the deleterious effects of herbicidally active 2- & 4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy! -Propionic acid derivatives of the formula II, wherein the substituents have the meaning given in the description by developing the crops, parts of these plants or soils intended for growing the crops with a compound of the formula I in which the substituents have the meaning given in the description, including their acid addition salts and metal complexes, or an agent which contains one of these compounds, treated. Formulas II and I

Description

Field of application of the invention

The present invention relates to the use of quinoline derivatives for protecting crop plants against harmful effects of herbicidally active 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid derivatives and herbicidal compositions comprising a combination of Contains herbicide and protective quinol derivative. Furthermore, the invention also relates to novel quinoline derivatives.

Characteristic of the known technical solutions

When using herbicides ₍ such as the above-mentioned propionic acid derivatives ₍ depending on factors ₍ such as dose of the herbicide and mode of application, type of crop, soil conditions and climatic conditions such as exposure time, temperature and precipitation levels, the crop plants can to a considerable extent In particular, severe damage may occur if, within the framework of crop rotation, crops that are resistant to the herbicides are cultivated with other crops which have no or only insufficient resistance to the herbicides.

It is known from European Patent Publications 86750 and 94349 that quinol derivatives can be used to protect crops against the harmful effects of aggressive agrochemicals.

Object of the invention

The invention provides a novel method of protecting crops from the deleterious effects of herbicides of the class of 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid derivatives when used for the purpose weed control applied to a crop culture.

Explanation of the essence of the invention

The invention is based on the object, special suitable agents for protecting the crop before the

find phytotoxic effects of this herbicide class.

It has now been found that, surprisingly, protection of crop plants against damage caused by herbicidally active 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid derivatives by treatment of the crop plants , can be obtained from parts of these plants or from crops for the cultivation of soils with a safener from a group of quinoline derivatives. The herbicidal activity against weeds and weeds is through

the quinoline derivatives are not removed.

Quinoline derivatives which protect herbicides from harmful effects 2- [4- (5-Chloro-3-)

fluoropyridin-2-yloxy) -phenoxy] -propionic acid derivatives are suitable, corresponding to the formula I.

ψ ψ-

VvV

I Il 1 (I),

in which R ¹ R ² and R ^3, independently of one another, are hydrogen, halogen, nitro, cyano, C ₁ -C ₃ -alkyl or C ₁ -C ₃ -alkoxy,

R ⁴ , R ⁵ and R ⁶ independently of one another are hydrogen, halogen or C ₁ -C ₃ -alkyl,

A is one of the groups -CH ₂ -, -CH ₂ -CH ₂ - or -CH (CH ₃ ) - and Z a) cyano or amidoxime which may be acylated on the oxygen atom

can, or

b) a carboxyl group or a salt thereof, a mercaptocarbonyl group or a salt thereof, a carboxylic acid ester group, a carbonyl thioester group, an unsubstituted or substituted carboxamide group, a cyclized, unsubstituted or substituted derivative of a carboxylic acid amide group or a carboxylic acid hydrazide group, or

A and Z together represent an unsubstituted or substituted tetrahydrofuran-2-one ring, including their acid addition salts and metal complexes.

Amidoxime is understood to mean the group-C (NH ₂ I = N-OH) The amidoxime can be acylated on the oxygen atom Suitable amidoximes which are acylated on the oxygen atom are those of the formula-C (NH ₂ J = NO-CO-E, in which E is -R ⁷ , -OR ⁸ , -SR ⁹

or -NR ¹⁰ R ¹¹ , where

R ^{7 is} C ₁ -C ₄ -alkyl which is unsubstituted or substituted by halogen or C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -cycloalkyl, C ₂ -C ₄ -alkenyl, phenyl which is unsubstituted or halogen, nitro or C ₁ -C ₃ -AlkYl substituted. Benzyl which is unsubstituted or substituted by halogen, nitro or C ₁ -C ₃ alkyl, or a 5- to 6-membered heterocyclic ring which has one or two

Contains heteroatoms from the group N, O or S and is unsubstituted or substituted by halogen,

R ⁸ , R ⁹ and R ¹⁰ independently of one another are C ₁ -C ₈ -alkyl which is unsubstituted or substituted by halogen, C ₂ -C ₄ -alkenyl, C ₃ -C ₆ -alkynyl, phenyl which is unsubstituted or halogen, C -AIRyI ₁ -C _3, C ₃ -alkoxy, trifluoromethyl or nitro

or benzyl which is unsubstituted or substituted by halogen or nitro, R ^{11 is} hydrogen, C ₁ -C ₈ -alkyl or C ₁ -C ₃ -alkoxy, or

R ¹⁰ and R "together with the nitrogen atom to which they are attached, a 5- to 6-membered heterocycle, which

may contain another heteroatom from the group N, O and S, mean.

When R ⁸ as heterocycle may be saturated, partially saturated or unsaturated heterocycles, such as

Thiophene, furan, tetrahydrofuran and pyrimidine.

Heterocycles which are formed by R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached are saturated, partially saturated or unsaturated heterocycles. Examples of such heterocycles are pyrrolidine, pyrroline, pyrrole, imidazolidine, imidazoline, imidazole, piperazine, pyridine, pyrimidine, pyrazine, thiazine, oxazole, thiazole and

in particular piperidine and morpholine.

Under alkyl as a constituent of the acylated amidoxime Z come within the specified number of

Carbon atoms all straight-chain and all branched alkyl groups into consideration.

In the meaning of R ⁷ , C 3 -C ₆ -cycloalkyl represents cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Of the C ₂ -C ₄ -alkenyl and Cs-Ce-alkynyl groups as constituents of the acylated amidoxime Z, vinyl, allyl,

To mention 1-propenyl, methallyl and propargyl.

For Z as Carbonsäureestergruppe or Carbonsäurethiolestergruppe a corresponding acid radical is contemplated, for example, by an optionally substituted aliphatic radical or an optionally bonded via an aliphatic radical and optionally substituted cycloaliphatic, aromatic or heterocyclic radical

is esterified.

The carboxylic acid ester radical preferred is the radical COOR ¹² and the carboxylic acid thioester moiety preferred is the radical COSR ¹³ , where R ¹² and R ^{13 have} the meanings given below: optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or naphthyl radical or optionally substituted heterocyclic radical. The radicals COOR ¹² and COSR ^{13 also} include the free acids wherein R ¹² and R ^{13 are} hydrogen and the salts thereof wherein R ¹² and R ^{13 are} a cation. Suitable salt formers are, in particular, metals and organic nitrogen bases, especially quaternary ammonium bases. Suitable metals for salt formation here are alkaline earth metals, such as magnesium or calcium, but especially the alkali metals, such as lithium and in particular potassium and sodium. Furthermore, as a salt former and transition metals such as iron, nickel, cobalt, copper, zinc, chromium or manganese are suitable. Examples of suitable for salt formation nitrogen bases are primary, secondary or tertiary, aliphatic and aromatic, optionally am

Hydrocarbon rest hydroxylated amines, such as methylamine, ethylamine, propylamine, isopropylamine, the four isomeric butylamines, dimethylamine, diethylamine, dipropylamine, diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine, quinoline , Isoquinoline and also methanolamine, ethanolamine, propanolamine, dimethanolamine, diethanolamine or triethanolamine. As organic nitrogen bases are also quaternary

Ammonium bases into consideration.

Examples of quaternary ammonium bases are tetraalkylammonium cations in which the alkyl radicals are, independently of one another, straight-chain or branched C ₁ -C ₆ -alkyl groups, such as the tetramethylammonium cation, the tetraethylammonium cation

or the Trimethyläthylammoniumkation, as well as the trimethylbenzylammonium cation, the

Triäthylbenzylammoniumkation and the trimethyl-2-hydroxyäthylammoniumkation. Particularly preferred salt formers are the ammonium cation and trialkylammonium cations in which the alkyl radicals are independently straight-chain or branched, optionally substituted by a hydroxyl group Ci-C ₆ alkyl groups, especially CrC ₂ alkyl groups, such as the trimethylammonium cation, the Triäthylammoniumkätion and the tri - (2-hydroxyethylene) -

ammonium cation.

For Z as Carbonsäureamidgruppe is a corresponding amide radical into consideration, which may be unsubstituted or mono- or disubstituted on the nitrogen atom or in which the nitrogen atom is part of an optionally substituted heterocyclic radical. Substituents of the amide group are, for example, an optionally substituted aliphatic radical which is optionally bonded via an oxygen atom and an optionally substituted cyclic aliphatic, aromatic or heterocyclic radical bonded via an aliphatic radical

or to name an optionally mono- or disubstituted amino group.

Preferred carboxylic acid amide radical is ReSt-CONR ¹⁴ R ¹⁵ , wherein R ^{14 is} hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or naphthyl radical, an optionally substituted heterocyclic radical or an alkoxy radical, R ¹⁵ Hydrogen, amino, mono- or disubstituted amino or an optionally substituted alkyl, alkenyl, cycloalkyl or phenyl radical or R ¹⁴ and R ¹⁵ together with the nitrogen atom to which they are attached, for

an optionally substituted heterocyclic radical.

As substituents of the organic radicals R ^12, R ^13, R ¹⁴ and R ¹⁵ are, for example, halogen, nit ^r o, cyano, hydroxy, alkyl, haloalkyl, alkoxy, which may be interrupted by one or more oxygen atoms, alkylthio, halogenoalkoxy, hydroxyalkoxy, which may be interrupted by one or more oxygen atoms, hydroxyalkylthio, alkoxycarbonyl, amino, alkylamino, dialkylamino, hydroxyalkylamino, di- (hydroxyalkyl) amino, aminoalkylamino, cycloalkyl, optionally substituted phenyl, optionally substituted phenoxy or an optionally substituted heterocyclic radical in

Consideration.

Heterocyclic radicals as constituents of the carboxylic acid ester radical, the Carbonsäurethiolesterrestes and the Carbonsäureamidrestes are preferably 5- to 6-membered, saturated or unsaturated, optionally substituted monocyclic heterocycles having 1 to 3 heteroatoms from the group N, O and S to understand, such as furan,

Tetrahydrofuran, tetrahydropyran, tetrahydropyrimidine, pyridine, piperidine, morpholine and imidazole.

Cycloalkyl radicals as constituents of the carboxylic acid ester radical, the Carbonsäurethiolesterrestes and the Carbonsäureamidrestes are especially those having 3 to 8, especially 3 to 6, carbon atoms, to understand.

In the substituent Z as part of the carboxylic acid ester radical, the Carbonsäurethiolesterrestes and the

Carboxylamide groups present aliphatic, acylic radicals may be straight-chain or branched and contain

suitably up to a maximum of 18 carbon atoms. A smaller number of carbon atoms is common, in particular

with compound substituents, an advantage.

For Z as a cyclized derivative of a carboxylic acid amide group, in particular an optionally substituted oxazoline-2-one comes about.

yl radical, preferably an unsubstituted oxazolin-2-yl radical, into consideration.

A and Z may together form an optionally substituted tetrahydrofuran-2-one ring, with the unsubstituted tetrahydrofuran-2-one ring being preferred, especially the unsubstituted tetrahydrofuran-2-on-3-yl ring.

In the compounds of the formula I, halogen is fluorine, chlorine, bromine and iodine, in particular chlorine, bromine and iodine.

Suitable salt formers for acid addition salts are organic and inorganic acids. Examples of organic acids are acetic acid, trichloroacetic acid, oxalic acid, benzenesulfonic acid and methanesulfonic acid. Examples of inorganic acids are hydrochloric acid, hydrobromic acid, hydriodic acid, sulfuric acid, phosphoric acid, phosphorous acid

and nitric acid.

Suitable metal complexing agents are, for example, elements of the 3rd and 4th main group, such as aluminum, tin and lead, and the 1st to 8th subgroup, such as chromium. Manganese, iron, cobalt, nickel, zirconium, zinc, copper, silver and mercury.

The subgroup elements of the 4th period are preferred.

When in the compounds of the formula IA is -CH (CH ₃ ) -, the radical Z contains an asymmetric carbon atom or A and Z together form a tetrahydrofuran-2-one ring, optically isomeric compounds exist. In the context of the present invention, the corresponding compounds of the formula I are to be understood as meaning both the optically pure isomers and the isomer mixtures. Is in the presence of one or more asymmetric carbon atoms, the structure

not specified, it is always meant the mixture of isomers.

Particularly suitable for use according to the invention are compounds of the formula I in which R ¹ , R ² , R ⁴ , R ⁵ and R ^{6 are} hydrogen, R ^{3 is} hydrogen or chlorine and the radical -AZ is a group -CH ₂ -COOR ¹⁶ or -CH (CH ₃ I-COOR ¹⁶

wherein R ^{16 is} C ₁ -C ₄ -alkyl, C ₃ -C ₆ -alkenyl, phenylC 1 -C ₄ -alkyl or phenoxy-C 1 -C ₄ -alkyl.

Preferred individual compounds of the formula I for use according to the invention are:

Isopropyl 2-quinoline-S-yloxyacetate, n-dodecyl 2- (5-chloro-quinoline-8-yloxy) -acetic acid, n-butyl 2- (5-chloro-quinolin-8-yloxy) -acetate, 2- (5 -Chloroquinolin-8-yloxy) -acetic acid-n-octyl ester, 2-quinolin-8-yloxy-acetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-octyl ester, 2- (5 -Chloroquinoline-8-yloxy) -acetic acid (2-butenyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid, methallyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-isopropyloxyethyl) ) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-Chloroquinoline-8-yloxy) -acetic acid cyclohexyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-methylpenty!) -ester, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid n-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3,6-dioxadecyl) ester, 2- (5-chloro) Chloroquinolin-8-yloxy) -acetic acid (3-methoxybutyl) ester, 2- (5-chloro-quino lin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid 2- (ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, n- undecyl 2- (5-chloro-quinolin-8-yloxy) -acetic acid, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (2-methylbutyl) -ester 2- (5-Chloroquinolin-8-yloxy) -thioacetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3,6-dioxaheptyl) ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid n-heptyl ester, n-dodecyl 2- (5-chloroquinolin-8-yloxy) thioacetic acid, n-decyl 2- (5-chloroquinolin-8-yloxy) thioacetic acid, 2- (5-chloroquinoline-8-yloxy) -thioacetic acid 5-chloroquinolin-8-yloxy) -acetic acid (1-propylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisobutyl) ester, 2- (5-chloroquinoline-8- yloxy) -thioacetic acid tert-butyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid neopentyl ester, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid n-propyl ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid (1-methylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) thioess ethyl acetate, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid i-butyl ester, 2-quinoline-S-yloxy- thioacetic acid-n-decyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid i-pentyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-ethylpentyl) -ester, 2- (5 -Chloroquinoline-8-yioxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-hexyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-hexyl ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid i-propyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-pentylallyl) ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1,1-dimethylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy ) -acetic acid (1-ethyl-1-methylpropargyl) ester,

2- (5-Chloroquinolin-8-yloxy) -acetic acid n-butyloxycarbonylmethyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-n-butyloxycarbonylethyl) ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) - acetic acid [1-methyl-2- (2-methylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5-chloroquinoline-8 -yloxy) -acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- (5-Chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-isopropylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylpropyl ) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (3-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, ^ - (B-chloroquinol nS-yloxyJ-acetic acid-CI-methyl-S-phenylpropyl-D, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (3-methylphenoxy) -ethyl] -ester, 2- (5-Chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-isopropylphenoxy) ethyl] ester and 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2 - (4-methylphenoxy) ethyl] ester. Particularly noteworthy in the context of the present invention is the use of: 2- (5-chloroquinolin-8-yloxy) -acetic acid ethelyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-Chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinoline-8 -yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-Ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-pentylallyl) - ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5 -Chloroquinoline-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- {5-chloroquinolin-8-yloxy ) -acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- { 5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylpropyl) ester, 2- (5- Chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester, and 2- (5 -Chlorchinolin-8-yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester. The following compounds have proved to be particularly effective for this purpose: 2- (5-chloroquinolin-8-yloxy) -acetic acid ethers, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) -esters, 2- (5-Chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester and 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester.

The following single-compound compounds of formula I, not yet disclosed, have been synthesized specifically for use as antidotes to the phytotoxic effect of 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid derivatives. They form a further subject of the present invention: 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloro-chino! in-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, 2 - (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid (1-pentylallyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (R-1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (S-1-methylisopentyl) ester, 2- {5-chloroquinolin-8-yloxy) -acetic acid ( R-1-methylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (S-1-methylhexyl) ester, ^ - (B-chloroquinolin-S-yloxyl-acetic acid-O-methylisohexyO- ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) acetic acid (1-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- {5-chloroquinolin-8-yloxy) -acetic acid (1-phenylpropyl) ester, 2- {5-chloroquinoline-8- yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester and 2- (5-chloroquinoline-8 yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester.

These new compounds are prepared in a conventional manner from a 2- (5-chloroquinolin-8-yloxy) -acetic acid derivative and a suitable alcohol by esterification or from 5-chloro-8-hydroxyquinoline and a suitable a-haloacetic acid ester in the presence of a Base made. Other suitable methods of preparation are described in published European patent application EP-A-94349.

Optically active isomers of the compound of the formula I can be prepared from the isomer mixtures by customary methods

Isomer separation process can be obtained. Advantageously, however, the pure isomers are prepared by selective synthesis from already optically active intermediates. For example, one may esterify a suitable 2- (5-chloroquinolin-8-yloxy) -acetic acid derivative with an optically active alcohol, or carry out the coupling of 5-chloro-8-hydroxyquinoline with an optically active α-haloacetic acid ester.

Examples of compounds to be used according to the invention having a protective action against herbicidal active 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid derivatives are shown in Table 1 below.

Table 1:

R ₃ R- / \ / \

Il

-A-Z

No. R ¹ R ² R ³ R ¹ * R ⁵ R ⁶ A Z CN physikal. constant 1.1 H H H H H H -CH ₂ - / NOH Mp 118-119 ° C 1.2 H H H H H H -CH ₂ - CN Mp. 201-204 ⁰ C (Zers.) 1.3 H H H H H CH ₃ -CH ₂ - NIH ₂ Mp 114-116 ° C L.A H H H H H CH ₃ -CH ₂ - v ^N0H NiH ₂ STNP. 2O9-21O ° C (decomp.) 1.5 H H Cl H H H -CH ₂ - / NO- (Z ~ ^C \ ih fin ^ Nn ₂ C3H7-X M.p. 2O3-2O5 ° C (decomp.) 1.6 H H H H H H -CH ₂ - Mp. 136-138 ⁰ C

Table 1 (continued)

No. R ¹ R ² R ³ R ¹ * R ⁵ R ⁶ A Z CN physikal. constant 1.7 H H Cl H H H -CH ₂ - A ° - <-C (CH ₂ Cl TiH ₂ Mp. 159-160 ⁰ C 1.8 H H H H H H -CH ₂ - -c ^ ^N0H Mp. 129-130 ⁰ C 1.9 br H Cl H H H -CH ₂ - CN Mp 197-198 ° C (decomp.) 1.10 br H Cl H H H -CH ₂ - -C ^ N) CH ₃ NH ₂ Mp 150-151 ° C 1.11 H H H H H H -CH ₂ - / NOH NIH ₂ Mp 143-145 ° C 1.12 J H Cl H H H -CH ₂ - CN Mp. 195-196 ° C (Zers.) 1.13 J H Cl H H H -CH ₂ - NlH ₂ J ₃ H ₇ -I Mp. 150.5-152 ⁰ C 1.14 br H Cl H H H -CH ₂ - Mp 162-165 ° C

Table 1 (continued)

No. R ¹ R ² R * H R ⁵ R ⁶ A Z physikal. constant 1.15 Cl H Cl H H H CH ₃ -CH ₂ - M.p. 2O5-2O7 ° C (decomp.) 1.16 1.17 Cl J H H Cl Cl H H H H H -CH ₂ - -CH ₂ - -CN β TiH ₂ C ₃ H ₇ -i Mp. 150-152 ⁰ C mp 163-167 ° C 1.18 Cl H Cl H H CH ₃ ™ 'C n2 "' CN Mp 157-158 ° C 1.19 Cl H Cl H H CH ₃ -CH ₂ - .NOC ^ ^N NH ₂ C ₃ H ₇ -i Mp 149-152 ° C 1.20 H H H H H H -CH ₂ CH ₂ - CN Mp 1O8-112 ° C 1.21 H H H H H H CH ₃ -CH- CN Mp 121-124 ° C 1.22 H H H H H -CH ₂ CH ₂ - \ η ₂ Mp 186-189 ° C

Table 1 (continued)

No. R ¹ R ² R ³ R ¹ * R ⁵ R ⁶ A Z CN physikal. constant 1.23 H H Cl H H H CH ₃ -CH- / NOH Mp 143-145 ° 1.24 H H H H H H CH ₃ -CH- / NOH ^ H ₂ Mp. 191-194 ° C (Zers.) 1.25 H H Cl H H H C * TJ V "3 -CH- CN Mp. 186-189 ° C (decomp.) 1.26 H H NO ₂ H H H CH ₃ -CH- Mp 154-156 ° C 1.27 Cl H NO ₂ H H H -CH ₂ - CN Mp 214-216 ° C (decomp.) 1.28 Cl H NO ₂ H H H -CH ₂ - -C ^ ^X C ₃ H ₅ -cycl. NH ₂ Mp 166-169 ° C 1.29 H H , H H H H -CH ₂ - Mp 165-166 ° C

Table 1 (Update)

No. R ¹ R ² R ³ R ¹ · R ⁵ R ⁶ A Z physikal. constant 1.30 H H H H H H -CH ₂ - -el Mp 139-141 ° C Cl 1.31 H H Cl H H H -CH ₂ - - (/ \ h ₃ NH ₂ Mp 141-143 ° C 1:32 H H NO ₂ H H H -CH ₂ - CN Mp. 162-164 ⁰ C 1:33 H H NO ₂ H H H -CH ₂ - ν ™ ^Ν ΝΗ ₂ Mp 212-215 ° C (decomp.) 1:34 H H Cl H H H -CH ₂ - / N-0-c / - (/ OCH ₃ IiH ₂ Mp 148-149 ° C

Table 1 (continued)

No. R ¹ R ² R ³ H R ⁵ R ⁶ A Z physikal. constant 1:35 H H Cl H H H -CH ₂ - -c'VC ₂ H ₅ NH ₂ Mp 139-140 ⁰ C 1:36 H H H H H H -CH ₂ - -CS-C ₅ HiI-η NH ₂ Mp 111-114 ° C 1:37 H H H H H H -CH ₂ - \ h ₂ ch CH ₃ Mp 158-162 ° C 1:38 H H H H H H -CH ₂ - ^ NH ₂ C ₂ H ₅ Mp 123-125 ° C 1:39 H H H H H -CH ₂ - -NOC ^ NH ₂ OCH ₃ Mp. 138-139 ° C

Table 1 (continued)

No. R ¹ R ² R ³ R " R ⁵ R ⁶ A Z physikal. constant 1:40 H H H H H H -CH ₂ - - </ NjuHg-n NH ₂ M.p. 12O-122 ° C 1:41 H H Cl H H H -CH ₂ - NOC (. -Cf _x C ₂ H ₅ NH ₂ Mp 157-158 ° C (decomp.) 1:42 H H H H H H -CH ₂ - - "-. yn ₂ NH ₂ CH ₂ CH ₂ Cl Mp. 144-146 ° C 1:43 H H H H H H -CH ₂ - -C ^ ^X CHC1 NH ₂ CH ₂ Cl Mp 112-114 ° C 1:44 H H Cl H H H -CH ₂ - N-O-C -C C3H7-I NH ₂ Mp 173-174 ° C

Table 1 (continued)

No. R ¹ R ² R ³ R " R ⁵ R ⁶ A Z physikal. constant 1:45 H H H H H H -CH ₂ - / N-O-C ^ Mp 155-156 ° C ^ NH ₂ J ^ Ii V 1:46 H H H H H H -CH ₂ - -C CitH ₉ -t. NH ₂ M.p. 1O7-11O, 5 ° C 1:47 H H H H H H -CH ₂ - ^N NH ₂ Mp 124-126 ° C 1:48 H H H H H H -CH ₂ - , NOC ^ -C ^ \ Cl NH ₂ S. Mp 131-132 ° C V

Table 1 (continued)

No. R ¹ R ² R ³ H R ⁵ R ⁶ A Z physikal. constant 1:49 H H H H H H -CH ₂ - .NOC ^ " ^C C f ² NH ₂ 0-Ci ₄ H ₉ -S. Mp 84-86 ° C 1:50 H H H H H H -CH ₂ - ~ \ π 5 5 Mp 168-169 ° C 1:51 H H H H H H -CH ₂ - WU ₂ · """· Mp. 100-103 ⁰ C 1:52 H H Cl H H H -CH ₂ - NlH ₂ O Mp. 156-157 ⁰ C (Zers.) 1:53 H H H H H -CH ₂ - Mp 82-85 ° C -df \ ₃ H ₇ -n NH ₂

Table 1 (continued)

No. R ¹ R ² R ³ R ¹ * R ⁵ R ⁶ A Z physikal. constant 1:54 H H H H H H -CH ₂ - , NOC ^ <S NH ₂ C ₃ H ₇ -n Mp. 144-147 ° C 1:55 H H H H H H -CH ₂ - NH ₂ CH ₂ Mp 128-130 ⁰ C 1:56 H H H H H H -CH ₂ - JJ-OC ^ -C ^ NH-C ^ H ₉ -n NH ₂ Mp 1O4-1O7 ° C 1:57 H H H H H H -CH ₂ - - <? \ η ₂ Βγ NH ₂ Mp 132-134 ° C 1:58 H H H H H H -CH ₂ - \ h ₂ CH ₂ Mp. 138-140 ⁰ C

Table 1 (continued)

No. R ¹ R ² R ³ R * R ⁵ R ⁶ A NjH ₂ Z \ CH ₂ physikal. constant 129-131 ⁰ C 1:59 H H H H H H -CH ₂ - / NO- \ h ₂ C14H9- η CH ₂ Mp. 121-123 ⁰ C 1.60 H H H H H H -CH ₂ - \ η ₂ CH ₂ CH ₂ Br Mp. 123-125 ⁰ C 1.61 H H H H H H "~ CH 2 *" Mp. ₂ ^N o- C ₃ H ₅ -CyCl. 127-128 ° C (Zers.) 1.62 H H H H H H -CH ₂ - / Mp. ₂ 173-175 ⁰ C 1.63 H H Cl H H H -CH ₂ - Mp.

J Ca) Et

Table 1 (continued)

No. R ¹ R ² R ³ R " R ⁵ R ⁶ A Z physikal. constant 1.64 H H H H H H -CH ₂ - JO -c '0-CH ₂ Mp 135-137 ° C / \ I Il V 1.65 H H Cl H H H -CH ₂ - " ^c \ _ Γι ij Smp.l91-192 ° C (Zers.) _N _ ₀ _ _c / 1.66 H H H H H H -CH ₂ - - (/ ^N SC ₂ H ₅ NiH ₂ M.p. 12O-121 ° C 1.67 H H H H H H -CH ₂ - / NOC ^ -c (CH ₂ IMHo Ω Mp 118-120 ⁰ C CH ₃

Table 1 (continued)

No. R ¹ R ² R ³ R * R ⁵ R ⁶ A Z physikal. constant 1.68 H H Cl H H H -CH ₂ - ^ -O-C ^ Mp.191-192 ° C (Zers.) I Il \ (· 1.69 H H H H H H -CH ₂ - - ^c (' ^oc ) \ Mp 158-159 ° C V " 1.70 H H H H H H -CH ₂ - -C ^ \ 3H7-i TJH ₂ Mp 115-117.5 ° C 1.71 H H H H H H -CH ₂ - \ h ₂ y ^ ΐ Γι ν Mp 140-142 ⁰ C

Table 1 (continued)

No. R ¹ R ² R » R ¹ * R ⁵ R ⁶ A Z physikal. constant 1.72 H H H H H H -CH ₂ - " ^C \ h ₂ S_S Snip. 164-165 ° C 1.73 H H H H H H -CH ₂ - - (/ N) -C ₂ H ₅ NH ₂ Mp. 129-132 ° C 1.74 H H H H H H -CH ₂ - Mp 155-157.5 ° C \ Γι V 1.75 H H H H H H ¹ -CH ₂ - / N-O-C ^ Mp. 158-160 ⁰ C I Γι v \ f,

Table 1 (continued)

No. R ¹ R ² R ³ R * R ⁵ R ⁶ A Z physikal. constant 1.76 H H Cl H H H -CH ₂ - - (/ \ h ₂ ci NH ₂ Mp 155-158 ° C (decomp.) 1.77 H H H H H H -CH ₂ - / NOC ^ NlH ₂ Mp. 144-146 ° C 1.78 H H H H H H -CH ₂ - / No-cr 'NiH ₂ C ₃ H ₇ -i Mp 123-124 ° C 1.79 H H H H H H -CH ₂ - / N-O-C ^ Mp. 173-176 ° C (Zers.) ^ (J ⁰¹ Cl 1.80 H H H H H H -CH ₂ - -c ( ^X CH ₂ NH ₂ CH ₂ Cl Mp 134-136 ° C (decomp.)

Table 1 (continued)

No. R ¹ R ^z R ³ R ¹ * R ⁵ R ⁶ A Z phyeikal. constant 1.81 H H H H H H -CH ₂ - NO-Cff -er CH ₃ NH ₂ Mp. 100-102 ⁰ C 1.82 H H H H H H -CH ₂ - / NOC ^ ^N NH ₂ , · Cl Mp 197-199 ° C I H c / V 1.83 H H H H H H -CH ₂ - NOC (^ O _x \ ", H" I Mp. 17O-171 ° C Nna · · 1.84 Cl H Cl H H H -CH- CH ₃ -COOCH ₃ Mp. 65-66 ° C 1.85 H H H H H H -CH- CH ₃ -COOCH ₃ M.p. 7O-72 ° C 1.86 H H H H H H -CH ₂ - -COOH .H ₂ O Mp 184-185 ° C 1.87 H H H H H H -CH ₂ - -COOCH ₂ CH ₂ OCH ₃ M.p. 8O-82 ° C

Table 1 (continued)

No. R ¹ R ² R ³ R ¹ * R ⁵ R ⁶ A Z -COOCH ₃ physikal. constant 1.88 H H H H H H -CH ₂ - -COOC ₂ H ₅ .H ₂ O M.p. 46.5-67, O ⁰ C 1.89 H H H H H H -CH ₂ - -CONH (CH ₂ ) 3OC ₂ H ₅ Mp. 56-59 ° C 1.90 H H H H H H / tTJ CH ₃ -CONHC ₂ H ₅ Mp 54-56 ° C 1.91 H H H H H H -CH- CH ₃ -COOC ₃ H ₇ -n Mp. 86-88 ⁰ C 1.92 H H H H H H -CH ₂ - -COOC ₃ H ₇ -I Mp. 28-31 ° C 1.93 H H H H H H -CH ₂ - -CONHCH3 · H ₂ O n ^ ³ - 1.5696 1.94 L H H H H H -CH ₂ - CH ₃ -CON ^ CH ₃ Mp. 74-81 ° C 1.95 H H H H H H -CH ₂ - -CONHC ₂ H ₅ Mp 142-145 ° C 1.96 H H H H H H -CH ₂ - -CONH (CH ₂ ) 3OH 07 s »p - 1.6002 1.97 H H H H H H -CH- CH ₃ -COOCH ₂ CH ₂ OC ₂ H ₅ M.p. 12O-122 ° C 1.98 H H H H H H -CH ₂ - 24 n ^ = 1.5673

Table 1 (continued)

R ¹ R ² R ³ R ¹ * R ⁵ R ⁶ A Z CH ₂ CH ₂ OH physikal. No. H H H H H H -CH- CH ₃ -CONHCHZ- · ^ / · • te · / CH ₃ -CON ^ constant 1.99 H H H H H H -CH ₂ - -CONH (CHa) ₃ CH ₃ CH ₂ CH ₂ OH Mp. 88-90 ⁰ C 1100 .CH ₃ -COOCHz-J } 0 M.p. 66-68 ° C H H H H H H -CH- CH ₃ -CON ^ -CONH (CHz) ₃ CH ₃ .H ₂ O 1101 -CH ₂ - - ^C ° - <...> n ²² »1.6054 H H H H H H 1102 -CH ₂ - Mp. 146-149 ° C H H H H H H CH ₃ 1103 H H H H H H -CH- CH ₃ tough mass 1104 H H H H H H Mp. 73-76 ° C 1105 M.p. 12O-121 ° C

CO IvJ

Table 1 (continued)

No. R ¹ R ² R ³ R ¹ » R ⁵ R ⁶ A Z physlkal. constant 1106 H H H H H H -CH- CH ₃ .CH ₃ -CON ^ CH ₃ Mp 105-111 ° C 1107 H H Cl H H H -CH ₂ - COOH Mp 232-233 ° C 1108 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OCH ₃ Mp 97-98 ° C 1109 H H Cl H H H -CH ₂ - -COOCH ₃ Mp. 104 to 105.5 ⁰ C 1110 H H Cl H H H -CH ₂ - -COOC ₂ H ₅ Mp. 116-117 ⁰ C 1111 H H Cl H H H -CH ₂ - -COOC ₃ H ₇ -n Mp. 108-109 ⁰ C 1112 H H Cl H H H -CH ₂ - .CH ₃ -CON ^ CH ₃ Mp 135-136 ° C 1113 H H H H H CH ₃ -CH ₂ - -COOCH ₃ Mp. 58-66 ° C 1114 H H H H H CHj -CH ₂ - -COOC ₂ H ₅ n ^ ² ' ⁵ = 1.5762 1115 H H Cl H H H -CH ₂ - -COOCitHg-t Mp. 63-69 ⁰ C 1116 H H H H H H -CH ₂ - -COOCjHg-t Mp. 68-70 ° C

Table 1 (continued)

No. R ¹ R ² R ³ R * R ⁵ R ⁶ A Z physikal. constant 1117 H H Cl H H H -CH ₂ - -COOCH ₂ -CsCH Mp 115-116 ° C 1118 H H Cl H H H -CH ₂ - -COOC ₃ H ₇ -I Mp. 147-148 ⁰ C 1119 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OC ₂ H ₅ Mp. 102-104 ⁰ C 1120 H H Cl H H H -CH ₂ - -COOCH ₂ - *; ' ^ · • BC · Mp. 110-112 ⁰ C. 1121 H H Cl H H H -CH ₂ - -COOCH ₂ -CH = CH ₂ Mp. 98-99 ° C 1122 H H Cl H H H -CH ₂ - -COO (CH ₂ ) iCH ₃ Mp. 76-77 ° C 1123 H H Cl H H H -CH ₂ - -COOCi ₁ H ₃ -S Mp. 110-111 ⁰ C 1124 H H H H H H -CH ₂ - -COO (CH ₂ ) ₇ CH ₃ n ^ ⁴ = 1.5419 1125 H H Cl H H H -CH ₂ - -COOCijHgn Mp 90.5-92 ⁰ C 1126 H H H H H H -CH ₂ - -COO (CH ₂ ) iCH ₃ 23 n ^ - 1.5232 1127 H H H H H H -CH ₂ - -COOCH ₂ -CH = CH ₂ 23 n ^ = 1.5885 1128 H H Cl H H H -CH ₂ - -COO (CH ₂ ) 7 CH3 Mp. 87-88 ° C

Table 1 (continued)

No. * R ¹ R ² H R ¹ · R ⁵ R ⁶ A Z physikal. constant 1129 H H H H H H , -CH ₂ - -COOC, Η 9-n 22n £ - 1.5642 1130 H H Cl H H H -CH ₂ - -COOCi ₄ H ₉ -S red OeI 1131 H H H H H H -CH ₂ - -COOCH ₂ CH ₂ Cl Mp 125-126 ° C 1132 H H Cl H H H -CH ₂ - -COOCH ₂ - ^ ^ · • SC · 23 5 n "' ³ - 1.6099 1133 H H Cl H H , H -CH ₂ - -COOCH ₂ -IJ 0 Mp 101-103 ⁰ C 1134 H H H H H H -CH ₂ - -COS (CH ₂ ) 7 CH 3 Mp. 53-54 ° C 1135 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ Cl Mp. 109-110 ⁰ C 1136 J H Cl H H H -CH ₂ - -C00CuH ₉ -t Mp 81-97 ° C 1137 J H Cl H H H -CH ₂ - -COOC ₂ H ₅ Mp. 92-94 ° C 1138 J H Cl H H H -CH ₂ - -COO (CH ₂ ) iCH ₃ Mp 51-53 ° C 1139 J H H H H -CH ₂ - -COOCH ₃ Mp 121-126 ° C

Table 1 (continued)

No. R ¹ R ² R ³ R ¹ * R ⁵ R ⁶ A Z physikal. constant 1140 J H Cl H H H -CH ₂ - , -COOCH ₂ CH ₂ Cl Mp. 44-45 ° C 1141 J H Cl H H H -CH ₂ - -COOCH ₂ - ^ \ • SE · Mp 112-113 ° C 1142 J H Cl H H H -CH ₂ - -COOC ₃ H ₇ -Ii Mp. 71-73 ° C 1143 H H H H H H -CH ₂ - -COOCnH ₉ -I 22 n ^ - 1.5632 1144 H H H H H H -CH ₂ - -COOCHCH2CH2CH3 CH ₃ 22 n ^ = 1.5391 1145 H H H H H H -CH ₂ - -COOCH (CH ₂ ) 5 CH3 22 n ~~ «1.5342 CH ₃ U _ 1146 H H H H H H -CH ₂ - -CONH (CH ₂ ) iCH ₃ Mp 56-61 ° C 1147 H H H H H H -CH ₂ - · - · '-CONHCH ₂ CH ₂ -N ^ \ - · · Mp. 94-99 ° C 1148 H H H H H H -CH ₂ - -CONHCH ₂ CH ₂ Ch ₂ OH Mp. 138-139 ° C 1149 H H H H H H -CH ₂ - · - · -CONH- S H \ "- · Mp 1O4-1O6 ° C

Table 1 (continued)

No. R ¹ R ² R ³ * R ⁵ R ⁶ A Z physikal. constant 1150 H H H H H H -CH ₂ - Mp. 99-103 ⁰ C 1151 H H H H H H -CH ₂ - / C ₂ H ₅ -CONHCH ₂ CH ₂ N ^ C ₂ H ₅ 23 n ^ »1.5686 1152 H H H H H H -CH ₂ - CH ₂ CH ₂ OH-COl / CH ₂ CH ₂ OH Mp. 144-146 ° C 1153 H H H H H H -CH ₂ - / CH ₃ -CONH (CH ₂ ) ₃ ϊ / CH ₃ 23 years - 1.5766 1154 H H H H H H -CH ₂ - / CH ₃ -COl / C, H ₉ -n 22n £ - 1.5840 1155 H H H H H H -CH ₂ - -CONHCH ₂ - *; ' ^ * · H ₂ O • 3X * Mp 7O, 5-73.5 ° C 1156 H H H H H H -CH ₂ - -CONHCHCH ₂ Ch ₃ CH ₂ OH Mp. 150-151 ⁰ C

Table 1 (continued)

No. R ¹ R ² R ³ R " R ⁵ R ⁶ A Z physikal. constant 1157 H H H H H H -CH ₂ - Ci, H9-n -CON ^ · 2H ₂ O Ci) Hg-η Mp. 105-106 ⁰ C 1158 H H H H H H -CH ₂ - -CONHCH ₂ CH ₂ -N ^ \ - · tip ⁶ - 1.5821 1159 H H H H H H -CH ₂ - CH ₂ CH ₂ OH -CONH (CH ₂ ) ₃ N ^ / CH ₂ CH ₂ OH Mp. 109-110 ⁰ C 1160 H H H H H H -CH ₂ - -CONHCH ₂ -CH-CH ₂ .H ₂ O Mp. 71-75 ° C 1161 H H H H H H -CH ₂ - -CONHCH ₂ - * · · H ₂ O 0 Mp 57-58 ° C 1162 H H H H H H -CH ₂ - -CONH (CH ₂ ) 3OC ₂ H ₅ Mp 51-61 ° C 1163 H H H H H H -CH ₂ - -CONHCh ₂ CH ₂ NHCH ₂ CH ₂ OH M.p. 7O-91 ° C 1164 H H Cl H H H -CH ₂ - CONH (CH ₂ ) 3OC ₂ H5 Mp. 85-88 ° C 1165 H H Cl H H H -CH ₂ - .CH ₃ -CON ^ CH ₂ CH ₂ OH Mp 187-189 ° C

Table 1 (continued)

No. R ¹ R ^z R ³ R " R ⁵ R ⁶ A Z physikal. constant 1166 H H Cl H H H -CH ₂ - CH ₂ CH ₂ OH -CONION CH ₂ CH ₂ OH Mp 177-179 ° C 1167 H H Cl H H H -CH ₂ - -CON ^ \ Mp. 148-15O ⁰ C 1168 H H Cl H H H -CH ₂ - -CONHCH ₂ CH ₂ CH ₂ Oh Mp. 157-160 ⁰ C 1169 H H Cl H H H -CH ₂ - f -uUWnttifng- Π · I12U M.p. 87-90 ⁰ C 1170 H H Cl H H H -CH ₂ - -CONHC ₂ H ₅ Mp. 94-98 ° C 1171 H H Cl H H H -CH ₂ - -CNHCH ₂ - · ^ ^ · · \ H ₂ O. Mp. 146-149 ⁰ C 1172 H H H H H CH ₃ -CH ₂ - -CONH ₂ Mp. 193-196 ⁰ C 1173 H H H H H H -CH ₂ - -CONHNH ₂ · H ₂ O Mp 121-124 ° C 1174 H H H H H H -CH ₂ - -COONa · H ₂ O Mp 140-142 ⁰ C 1175 H H · H H H H -CH ₂ - -COOK · H ₂ O Mp> 200 ^° C 1176 H H H H H H -CH ₂ - θ®-COO HN (CH ₃ ) 3 Mp 176-178 ° C

sj CO 4

Table 1 (continued)

No. R ¹ R ² R ³ R * R ⁵ R ⁶ A Z physikal. constant 1177 H H H H H H -CH ₂ - θ®-COO HN (CH ₂ CH ₂ OH) ₃ Mp 97-98 ° C 1178 H H Cl H H H -CH ₂ - -COOK · H ₂ O Mp.> 26O ° C 1179 H H Cl H H H -CH ₂ - -COONa · H ₂ O Mp> 260 ^° C 1180 H H H H H H -CH ₂ - θ®-COO HN (C ₂ Hs) ₃ Mp 255-257 ° C (decomp.) 1181 H H Cl H H H -CH ₂ - -COO® ® »» Mp. 227-228 ° C (decomp.) 1182 H H Cl H H H -CH ₂ - Θ®-COO HN (CH ₂ CH ₂ OH) ₃ Mp 132-156 ° C (decomp.) CH ₃ 1183 H H Cl H H H -CH- CH ₃ -COO- { V-CH3 M.p. 12O-122 ° C 1184 H H Cl H H H -CH ₂ - CH ₃ -COOCH (CH ₂ ) 5 CH ₃ Mp. 65-67 ° C 1185 H H Cl H H H -CH ₂ - -COOCH ₂ CH = CH-Ch ₃ Mp. 100-102 ⁰ C 1186 H H Cl H H H -CH ₂ - CH ₃ -COOCH ₂ -C = CH ₂ Mp 94-95 ° C

Table 1 (continued)

No. R ¹ R ^z R ³ R " R ⁵ R ⁶ A Z physlkal. constant 1187 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OC ₃ H ₇ -I Mp. 70-72 ⁰ C 1188 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ -O - »^") · Mp. 79-8O, 5 ° C 1189 br H br H H H -CH ₂ - -COOCH ₃ Mp 143-145 ° C 1190 br H Cl H H H -CH ₂ - -COOC ₃ H ₇ -I Mp. 71-73 ° C 1191 br H br H H H -CH ₂ - -COOC ₃ H ₇ -I Mp. 47-51 ° C 1192 Cl H Cl H H H -CH ₂ - -COOC, Η 9-n M.p. 42-43.5 ⁰ C 1193 br H Cl H H H -CH ₂ - -C00Ci, H9 n Mp. About 28 ° C 1194 Cl H Cl H H H -CH ₂ - -COO (CHa) ₇ CH ₃ Mp. About 30 ⁰ C 1195 br H Cl H H H -CH ₂ - -COO (CHa) ₇ CH ₃ Mp 41-42 ° C 1196 br H Cl H H H -CH ₂ - CH ₃ -COOCH (CH ₂ ) 5 CH ₃ Mp 46-48 ° C 1197 Cl H Cl H H H -CH ₂ - -COO (CH ₂ ) I ₁ CH ₃ Mp. 49-50 ⁰ C 1198 br H Cl H H H -CH ₂ - -COO (CH ₂ ) I ₁ CH ₃ Mp. 50-52 ⁰ C

Table 1 (continued)

No. R ¹ R ² R ³ * R ⁵ R ⁶ A Z physikal. constant 1199 Cl H Cl H H H -CH ₂ - -COOCH ₂ - '/ ^ * * SC · Mp. 79-80 ⁰ C 1200 br H Cl H H H -CH ₂ - • - * - COOCH ₂ - ''' y * • 31 · Mp. 100-102 ⁰ C 1201 br H br H H H -CH ₂ - -COOCH ₂ - '^ ^ · · se · Mp 101-104 ⁰ C 1202 br H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OCH ₃ Mp. 68-70 ⁰ C 1203 Cl H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OC ₂ H ₅ Mp. 81-82 ° C 1204 br H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OC ₂ H ₅ Mp. 71-72 ° C 1205 br H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OC ₃ H ₇ -I n £ ⁵ »1.5763 1206 br H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ O - '^ Ν »• S = · Mp. 80-82 ⁰ C 1207 Cl H Cl H H H -CH ₂ - I 1 Mp. 77-78 ° C

Table \ (. Continued)

No. R ¹ R ² R ³ R " R ⁵ R ⁶ A Z physikal. constant 1208 br H Cl H H H -CH ₂ - Mp. 79-80 ⁰ C 1209 Cl H Cl H H H -CH ₂ - -COOCH ₂ - * 'O Mp 72-73 ° C 1210 br H Cl H H H -CH ₂ - -COOCH ₂ CH = CH ₂ Mp 66-68.5 ° C 1211 br H br H H H -CH ₂ - -COOCH ₂ CH = CH ₂ Mp. 78-79 ° C 1212 br H Cl H H H -CH ₂ - -COOCH ₂ CH = CH ₂ Mp. 60-64 ⁰ C 1213 Cl H Cl H H H -CH ₂ - -COOCH ₂ CH = CH-Ch ₃ Mp. 62-65 ° C 1214 br H Cl H H H -CH ₂ - CH ₃ -COOCH ₂ -C = CH ₂ Mp. 62-64 ° C 1215 br H Cl H H H -CH ₂ - CH ₃ -COOCH ₂ -C = CH ₂ Mp 52-54 ° C 1216 H H Cl H H H -CH- CH ₃ -COO- S H ^ · n £ ⁴ - 1.5642 -COOC ₃ H ₇ -I

Table 1 (continued)

No. R ¹ R ² R ³ R " R ⁵ R ⁶ A Z physikal. constant 1217 H H Cl H H H -CH- CH ₃ -COO (CH ₂ ) 7 CH3 23 n ^ - 1.5356 1218 H H Cl H H H -CH- CH ₃ CH ₃ -COOCH (CH ₂ ) SCH ₃ η "- 1.5370 1219 H H Cl H H H -CH- CH ₃ -COO (CH ₂ ) iCH ₃ Mp. 54-55 ° C 1,220 1,221 H H H H Cl Cl H H H H H H SS SS o-o o-o -COOCH ₂ - * ^ ^ * • St - COOCH ₂ CH ₂ OC ₃ H ₇ - I Mp 57-59 ° C 32 njj - 1.5403 1222 H H Cl H H H -CH- CH ₃ -COOCH ₂ CH ₂ O - * ^ ^ · • ax « 29 n ^ «1.5962 1223 H H Cl H H H -CH- CH ₃ -COOCH ₂ CH = CH ₂ Mp. 40-41 ⁰ C 1224 H H Cl H H H -CH- CH ₃ -COOCh ₂ CH = CH-CH ₃ Mp. 39-40 ⁰ C

Table 1 (continued)

No. R ¹ R ² R ³ R- R ⁵ R ⁶ A Z physikal. constant 1225 H H Cl H H H -CH- CH ₃ CH ₃ -COOCH ₂ -C = CH ₂ Mp. 62-63 ° C 1226 H H Cl H H H -CH- CH ₃ · - * -COO- · ^ Η ^ · n ^ ° - 1.5677 1227 br H Cl H H H CH ₃ -COO (CH ₂ ) 7 CH ₃ n ^ ⁸ = 1.5439 1228 Cl H Cl H H H -CH- CH ₃ CH ₃ -COOCH (CH ₂ ) ₅ CH ₃ n "= 1.5408 1229 br H Cl H H H -CH- CH ₃ CH ₃ -COOCH (CH ₂ ) ₅ CH ₃ n ^ ⁵ - 1.5527 1230 br H Cl H H H V CH ₃ -C00 (CH ₂ ) ii CH ₃ nf - 1.5347 1231 br H Cl H H H -CH- CH ₃ -COOCH ₂ - · ^ ^ · XS · Mp 55-56 ° C

Table 1 (continued)

No. R ¹ R ² R ³ R * R ⁵ R ⁶ A Z physikal. constant 1232 br H Cl H H H -CH- CH ₃ -COOCH ₂ - '' 0 n ° 1.5886 1233 br H Cl H H H -CH- CH ₃ -COOCH ₂ CH ₂ OC ₃ H ₇ -I n ^ ⁸ «1.5642 1234 br H Cl H H H -CH- CH ₃ -COOCH2CH2 0- · ^^ · • SE · n ° 1.6031 1235 br H Cl H H H -CH- CH ₃ -COOCH ₂ CH = CH ₂ Mp 55-56 ° C 1236 Cl H Cl H H H -CH- CH ₃ -COOCH ₂ CH = CH-Ch ₃ Mp 38-39 ° C 1237 br H Cl H H H -CH- CH ₃ -COOCH ₂ Ch = CH-CH ₃ Mp. 38-40 ⁰ C 1238 br H Cl H H H -CH- CH ₃ CH ₃ -COOCH ₂ C = CH ₂ OO n ^ - 1.5824 1239 H H Cl H H H -CH 2- COO -. ( "\ Mp 165-170 ° C

Table 1 (continued)

No. R ¹ H R ² R ³ R " R ⁵ R ⁶ A Z physikal. constant 1240 H H H Cl H H H -CH ₂ - -COO- S ^ '- CH ₃ • SS · Mp 143-145 ° C 1241 H H Cl H H H -CH ₂ - COO / ""). Mp 111-116 ° C 1242 H Cl H H H -CH ₂ - COO ·; ' ^ '- CH ₃ • as Mp. 108-119 ⁰ C 1243 H Cl H H H -CH- CH ₃ COO / ""). • Bl Mp. 102-105 ⁰ C

Table 1 (continued)

No. R ¹ R ² R ³ H R ⁵ R ⁶ A + Z physikal. constant 1244 H H Cl H H · --- · j Mp. 140 to 141.5 ⁰ C

Table I (continued)

No. R ¹ R ² H R ³ Cl H R ⁵ H R ⁶ A Z physikal. constant 1245 H H H H H H -CH ₂ - CH ₃ -COOCHCH ₂ Ch ₂ CH ₃ Mp 65-70 ° C 1246 H H Cl H H H -CH ₂ - CH ₃ -COOCH ₂ -CH (CH ₂ ) ₂ CH ₃ 22n £ - 1.5525 1247 H H Cl H H H -CH ₂ - -COO- S H ^ · Mp 112-113 ° C 1248 H H H H H H -CH ₂ - CH ₃ -COOCH ₂ CH-CH ₃ Mp. 113-114 ° C 1249 H H H H H H -CH ₂ - QCH ₃ -COO (CH ₂ ) ₂ CHCH ₃ n ²² = 1.5580 1250 H H H H H H -CH ₂ - -COOCH ₂ CH ₂ OCH ₂ CH ₂ O (Ch ₂ ) ₃ CH ₃ n ²² = 1.5389 1251 H H H H H H -CH ₂ - -COS (CH ₃ ) ₃ CH ₃ n ²³ = 1.6096 1252 H H H H H H -CH ₂ - -COO- S H \ 23 n "» 1.5755 1253 H H H H H H -CH ₂ - -COO (CH ₂ ) 1, CH ₃ 23 n ^ -1.5591 1254 H H -CH ₂ - -COS (CH ₂ ) 7 CH ₃ 22 n ^ = 1.5697

Table 1 (continued)

No. R ¹ R ^z H R ³ Cl R " H R ⁵ H R ⁶ H A Z phyeikal. constant 1255 H H Cl H H H -CH ₂ - CH ₃ -COOCH ζ -CH (CH 2 ) 2 CH ₃ Smp.74-75 ° C 1256 H H H H H H -CH ₂ - -COS (CH ₂ ) 3 CH 3 22 n £ »1.6076 1257 H H H H H H -CH ₂ - -COOCH ₂ Ch = CH-CH ₃ 22 n £ = 1.5833 1258 H H Cl H H H -CH ₂ - C ₂ H ₅ -COOCH ₂ -CH-C ₂ H ₅ 23 Πρ »1.5530 1259 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OCH ₂ Ch ₂ O (CH ₂ ) SCH ₃ Mp. 39-41 ⁰ C 1260 H H Cl H H H -CH ₂ - OCH ₃ -COO (CH ₂ ) ₂ CHCH3 Mp 72-73 ° C 1261 H H Cl H H H -CH ₂ - -COO (CH ₂ ) ₁ , CH ₃ Mp. 78-79 ° C 1262 H H H H H H -CH ₂ - C ₂ H ₅ -COOCH- (CH ₂ ) ₂ CH 3 Mp 37-46 ° C 1263 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OC ₃ H ₇ -I 22 n ^ β 1.5546 1264 H H H H H H -CH ₂ - -COO (CH ₂ ) I ₃ CH ₃ Mp.75-76 ⁰ C 1265 H -CH ₂ - C ₂ H ₅ -COOCH-C ₂ H ₅ Mp 47-50 ⁰ C H H H H H CH ₃ ^ · - · 1266 H -CH ₂ - -COO- S H ^> · · Mp. 29-31 ⁰ C

Table 1 (continued)

No. R ¹ R ² Hv R ³ Cl R * H R ⁵ H R ⁶ H A Z physikal. constant 1267 H H H H H H -CH ₂ - C ₂ H ₅ -COOCH ₂ -CH-C ₂ H ₅ Mp. 58-63 ° C 1268 H H H H H H -CH ₂ - -COOCH ₂ CH ₂ OCh ₂ CH ₂ OC ₂ H ₅ n ^ ² = 1.5489 1269 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ O - * ^ ^ · Mp. 80-81 ⁰ C 1270 H H H H H H -CH ₂ - C ₂ H ₅ -COOCH-C ₂ H ₅ Mp 55-80 ⁰ C 1271 H H H H H H -CH ₂ - CH ₃ CH ₃ -COOCHCH ₂ CH-Ch ₃ 22n £ -1.5463 1272 H H H H H H -CH ₂ - -COO (CH ₂ ) I ₃ CH ₃ Mp 35-36 ° C 1273 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ O (CH ₂ ) ₃ CH ₃ 22 nj -1.5495 1274 H H H H H H -CH ₂ - -COOCH ₂ CH ₂ OCH ₂ CH ₂ OC ₂ Hs Smp.42-43 ° C 1275 H H Cl H H H -CH ₂ - CH ₃ -COOCH ₂ -CH-C ₂ H ₅ 22 n ^ «1.5566 1276 H H H H H H -CH ₂ - CH3 _CH3 CH3--COOCHCH2CH Smp.63-64 ° C 1277 H -CH ₂ - CH ₃ -COSCH-C ₂ H ₅ 22 η £ -1.5973

Table 1 (continued)

No. R ¹ R ² H R ³ Cl R * R ⁵ H R ⁶ H A Z physifcal. constant 1278 H H H H H H -CH ₂ - -COO- S H ^ · Smp.98-101 ° C 1279 H H H H H H -CH ₂ - CH ₃ -COOC-C ₂ H ₅ C ₂ H ₅ 22 »« -1.5551 1280 H H H H H H -CH ₂ - CH ₃ -COOCH ₂ -C = CH ₂ η ²² = 1.5805 1281 H H H H H H -CH ₂ - CH ₃ -COOC-CH = CH ₂ CH ₃ 22,000 pounds 1282 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OCH ₂ CH ₂ OCh ₃ 23 η "» 1.5560 1283 H H Cl H H H -CH ₂ - CH ₃ -COOC-C ₂ H ₅ C ₂ H ₅ 22 n ^ »1.5632 1284 H H Cl H H H -CH ₂ - -COO (CH ₂ ) ioCHa Smp.7O-71 ° C 1285 H H H H H H -CH ₂ - CH ₃ -COOCH ₂ -CH-C ₂ Hs Smp.78-79 ° C 1286 H H -CH ₂ - -COO- · _χ Η ^ '- CH ₃ Smp.40-42 ° C

N) CT)

Table 1 (continued)

No. R ¹ R ² H R ³ H R * H R ⁵ H R ⁶ H A Z physlkal. constant 1287 H H H H H H -CH ₂ - -COO (CH ₂ ) ₆ CH ₃ n ^ ³ = l.5469 1288 H H Cl H H H -CH ₂ - CH ₃ -COOC-C ₂ H ₅ CH ₃ 22 n £ = 1.5581 1289 H H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ O (CH ₂ ) 3 CH 3 M.p. 69-70 ° C 1290 H H Cl H H H -CH ₂ - CH ₃ -COSCH-C ₂ H ₅ Mp 55-56 ° C 1291 H H H H H H -CH ₂ - CH ₃ -COOC-CH = CH ₂ CH ₃ Mp. 83-87 ° C 1292 H H Cl H H H -CH ₂ - -COSCH3 Mp. 41-44 ° C 1293 H H Cl H H H -CH ₂ - -COOCH2CH2OCH2CH2OCH3 23 n ^ = 1.5633 1294 H H Cl H H H -CH ₂ - -COSCH3 Mp. 89-91 ⁰ C 1295 H H H H H H -CH ₂ - CH ₃ -COOC-C ₂ H ₅ CH ₃ Mp. 53-54 ° C 1296 H H Cl H H H -CH ₂ - -COO (CH ₂ ) I ₀ CH ₃ np ³ -1.5310 1297 H -CH ₂ - -COO (CH ₂ ) GCH ₃ Smp.74-76 ° C

Table 1 (continued)

No. R ¹ R ² H R ³ H * R ⁵ H R ⁶ H A Z physikal. constant 1298 H H Cl H H H -CH ₂ - CH ₃ CH ₃ -COOCH-CH-CH ₃ 23 n ^ »1.5554 1299 H H H H H H -CH ₂ - -COO- * ' H '' / -CH ₃ Mp. 103-105 ⁰ C 1300 H H Cl H H H -CH ₂ - CH ₃ -COSC-CH ₃ CH ₃ 23 n £ »1.5987 1301 H H Cl H H H -CH ₂ - -COS (CHz) ₁ ICH ₃ Smp.26-28 ° C 1302 H H Cl H H H -CH ₂ - -COS (CHz) ₉ CH ₃ Mp.29-31 ⁰ C 1303 H H H H H H -CH ₂ - -COO (CHz) ₉ CH ₃ Smp.73-74 ° C 1304 H H Cl H H H -CH ₂ - CH ₃ -COOCH (CHz) 1, CH ₃ 23 n £ = 1.5433 1305 H H H H H H -CH ₂ - C ₃ H ₇ -n-COOCH-C = CH Mp. 81-82 ° C 1306 H H Cl H H H -CH ₂ - C ₅ Hi ₁ -H-COOCH-CH-CHz n ^ ³ «1.5472 1307 H H Cl H H H -CH ₂ - CH ₃ CH ₃ -COOCH-CH-CH ₃ Smp.7O-74 ° C 1308 H H -CH ₂ - CH ₃ -COSC-CH ₃ CH ₃ 22 n £ = 1.5996

Table 1 (continued)

No. R ¹ R ² H R ³ H R ¹ * H R ⁵ H R ⁶ H A Z physikal. constant 1309 H H H H H H -CH ₂ - CH ₃ -COOCH-C = CH 23 n ^ = 1.5837 1310 H H H H H H H H H H H -CH ₂ - -COS (CH ₂ ) I ₁ CH ₃ 23 ηJ -1.5523 1,311 1,312 H H H Cl H H H -CH ₂ - -CH ₂ - CH ₃ -COOCH ₂ -C-CH ₃ CH ₃ -COSC ₂ H ₅ 22 years "1.5524 23 n ^ -1.6310 1313 H H Cl H H H -CH ₂ - CH ₃ -COOCH ₂ -C-CH ₃ CH ₃ Smp.76-81 ° C 1314 H H H H H H -CH ₂ - -COSC ₃ H ₇ -n np ² = 1.6136 1315 H H Cl H H H -CH ₂ - -C00 (CH ₂ ) ₉ CH 3 22 n ^ -1.5308 1316 H H H H H H -CH ₂ - CH ₃ -COOCH (CHa) ₁₁ CH ₃ Smp.65-67 ° C 1317 H H H H H H -CH ₂ - CH ₃ -COO (CHa) ₂ CH-CH ₃ 23 n £ -1.5568 1318 H H Cl H H H -CH ₂ - CaH ₅ -COOCH (CHa) ₃ CH ₃ 22 n ^ = 1.5454 1319 H -CH ₂ - -COO (CH ₂ ) ₈ CH ₃ Smp.78-79 ° C

• »CO

Table 1 (continued)

No. R ¹ R ² H R ³ H R * H R ⁵ H R ⁶ H A Z physikal. constant 1320 H H Cl H H H "CH2 ™ * CH ₃ -COSCH ₂ CHCH ₃ 23 n * »1.6049 1321 H H H H H H -CH ₂ - -COSC ₂ H ₅ Smp.55-57 ° C 1322 H H Cl H H H "* C n2" ~ -COO (CH ₂ ) ₈ CH ₃ n ^ ⁴ = l.5436 1323 H H Cl H H H -CH ₂ - CaH ₅ -COOCH ₂ -CH (CH ₂ ) ₃ CH ₃ Mp. 45-47 ° C 1324 H H H H H H -CH ₂ - CH ₃ -COSCH ₂ CH-CH ₃ n ^ = 1.6045 1325 H H Cl H H H -CH ₂ - -COS (CH ₂ ) 9CH ₃ 23 n ^ = 1.5630 1326 H H Cl H H H -CH ₂ - CH ₃ -COO (CH ₂ ) ₂ CH-CH ₃ Smp.72-74 ° C 1327 H H H H H H "" CH2 "" C ₂ H ₅ -COOCH (CH ₂ ) 3 CH 3 22 n ^ = 1.5542 1:32 " H H H H H H -CH ₂ - -COO (CH ₂ ) 5 CH3 22 n ^ = 1.5512 1329 H H H H H H -CH ₂ - C 3 H 7 -η-COOCH (CHa) ₂ CH ₃ Mp 48-50 ° C 1330 H H H H H H -CH ₂ - -COS (CH ₂ ) I ₁ CH ₃ 22 n £ = 1.5937 1331 H -CH ₂ - -COSC ₃ H ₇ -IsO 23 n ^ = 1.5821

Table 1 (continued)

No. R ¹ R ² H R ³ H R " H R ⁵ H R ⁶ H A Z physikal. constant 1332 H H Cl H H H -CH ₂ - C ₂ H ₅ -COOCH ₂ CH- (CH ₂ ) 3 CH 3 22NJ-1.5395 1333 H H Cl H H H -CH ₂ - CsHy-n-COOCH (CH ₂ ) ₂ CH ₃ Smp.55-57 ° C 1334 H H Cl H H H -CH ₂ - COS (CH ₂ ) 5CH ₃ 22 n * »1.5882 1335 H H Cl H H H -CH ₂ - -COS (CH ₂ ) I ₄ CH ₃ n ^ ³ »1.5990 1336 H H Cl H H H -CH ₂ - -COO (CH ₂ ) 5 CH3 Smp.71-72 ° C 1337 H H Cl H H H -CH ₂ - -COSC ₃ H ₇ -IsO. Smp.62-64 ° C 1338 H H H H H H -CH ₂ - C ₂ H ₅ CH ₃ -COOCH-CH ₂ CHC ₂ H ₅ Smp.25-29 ° C 1339 H H H H H H -CH ₂ - CsH ₇ -I-COOCH-C ₃ H ₇ -I n ^ ² -1.5468 1340 H H Cl H H H -CH ₂ - CH ₃ -COOCH- (CH ₂ ) ₃ CH ₃ 23 n ^ -1.5531 1341 H H H H H H -CH ₂ - CsHii-n-COOCH ₂ CH = CH np ³ «= 1.5579 1342 TT -CH ₂ - C2H5 -COOCH- (CH ₂₎ 2 CH ₃ Smp.42-44 ° C

• sj (0

Table 1 (continued)

No. R ¹ R ² H R ³ H R ¹ * H R ⁵ H R ⁶ H A Z physikal. constant 1343 H H Cl H H H -CH ₂ - -COSC ₃ H ₇ -n 22 n * = 1.6108 1344 H H H H H H -CH ₂ - CH ₃ -COOCH- (CH ₂ ) ₃ CH ₃ Smp.68-71 ° C 1345 H H Cl H H H -CH ₂ - C2H5 CH ₃ -COOCH ₂ CHC ₂ H ₅ year ³ -1.5472 1346 H H H H H H -CH ₂ - C ₃ H ₇ -I-COOCH-C ₃ H ₇ -I Smp.88-89 ° C 1347 H H H H H H -CH ₂ - -COS (CH ₂ ) 5 CH 3 22 nj = 1.5804 1348 H H H H H H -CH ₂ - -COO (CH ₂ ) 9-CH = CH ₂ 22 n ^ = 1.5386 1349 H H Cl H H H -CH ₂ - C ₃ H ₇ -n-COOCH-C = CH 22,000 pounds 1350 H H H H H H -CH ₂ - CH ₃ -COOCH-C = CH Smp.97-100 ° C 1351 H H Cl H H H -CH ₂ - CH ₃ -COOC-C = CH C ₂ H ₅ 22n £ -1.5688 1352 H H Cl H H H -CH ₂ - -COO (CH ₂ ) 9-CH = CH ₂ Smp.66-67 ° C 1353 H -CH ₂ - CH ₃ -COO-CC = CH CH ₃ Smp.76-81 ° C

Table 1 (continued)

No. R ¹ R ² H R ³ H R- H R ⁵ H R ⁶ H A Z physikal. constant 1354 H H Cl H H H -CH ₂ CH ₃ -COO-C-CsCH OH ₃ 23n * -1.5740 1355 H H Cl H H H -CH ₂ - CH ₃ -COO-C-C ash CH ₂ Hs Smp.78-79 ° C 1356 H H Cl H H H -CH ₂ - CH ₃ CH ₃ -COO-CH-CH-C ₂ H ₅ Smp.71-73 ° C 1357 br H Cl H H H -CH ₂ - -COOCH ₃ Smp.l26-128 ° C 1358 br H Cl H H H -CH- CH ₃ -COOC ₃ H ₇ -I Smp.66-68 ° C 1359 Cl H Cl H H H -CH ₂ - -COOCH ₂ CH ₂ OCH ₃ Smp.68-7O ° C 1360 Cl H Cl H H H -CH ₂ - -COOC ₃ H ₇ -I Smp.60-63 ° C 1361 H H Cl H H H -CH- CH ₃ -COOCH _{2 x} -I y njj ° -1.5734 1362 H H Cl H H H -CH ₂ - -COOCH ₂ COOCi, H ₉ -n Smp.52-54 ° C 1363 H -CH ₂ - -COOCH-COOCuHg-n CH ₃ 22n £ = 1,5508

Table 1 (continued)

No. R ¹ R ² Cl R- R ⁵ R ⁶ A Z physikal. constant 1364 H H Cl H H H -CH ₂ - CH ₃ CH ₃ -COOCHCH ₂ CH ζ CH-CH ₃ Mp 55-59 ° C 1365 H H H H H -CH ₂ - -COOCH- ^ ^ - Mp 43-47 ° C Cl r ^CH3 > - \ 1366 H H H H H -CH ₂ - -COOCHCH ₂ O- ^ ^ · Mp. 75-78 ° C Cl Cl CH ₃ 1,367 1,368 H H H H Cl H H H H H H -CH ₂ - -CH ₂ - -COOCH- ^ ^ · CH ₃ -COOCHCH ₂ O- ^ ^) - C ₂ H ₅ Mp. 117-122 ⁰ C mp. 63-68 ° C 1369 H H Cl H H H -CH ₂ - -COOCHCH ₂ - ^^ · · = · Mp 116-118 ° C 1370 H H H H H -CH ₂ - C 1-4 -COOCH-CH ₂ O- ^^ M.p. 41 ~ 43 ° C

Table 1 (continued)

No. R ¹ R ² R ³ R * R ⁵ R ⁶ A Z physikal. constant 1371 H H Cl H H H -CH ₂ - C ₂ Hs -COOCH- / · Mp. 74-76 ° C CH ₃ ^{2 5} \ _ _# 1372 H H Cl H H H -CH ₂ - -COOCHCH ₂ O- ^ ^ · Mp. 96-98 ° C / C ₂ H ₅ 1373 H H Cl H H H -CH ₂ - -COOCHCH ₂ O- ^ ^ · Mp 82-85 ° C 1374 H H Cl H H H -CH ₂ - CH ₃ \ 2 \ -COOCHCH ₂ O- ^^ Mp 42-44 ° C CH ₃ * ⁼ [_ _# 1375 H H Cl H H H -CH ₂ - -COOCHCH ₂ CH ₂ - ^ ^ · r = · Mp. 78-79 ° C CH _{3 m} _y ³ 1376 H H Cl H H H -CH ₂ - -COOCHCH ₂ O- ^ / · Mp. 58-61 ° C CH ₃ 1377 H H Cl H H H -CH ₂ - -COOCHCH ₂ O- ^ ^) - C ₃ H ₇ -I · = · Mp. 35-38 ° C CH ₃ 1378 H H Cl H H H -CH ₂ - -COOCHCH ₂ O- ^ / -CH ₃ · = · Mp 82-84 ° C

The compounds of formula I can be prepared by known methods, as described for example in European Patent Publications 86750 and 94349, or can be prepared analogously to known methods. The quinoline derivatives of the formula I have outstanding properties of protecting crop plants against damaging effects of herbicidally active 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid derivatives. The abovementioned herbicidal active compounds are known from the published European patent applications EP-A-83556 and EP-A-97460 and can be prepared by the methods indicated there. Particularly effective and employable according to the teaching of the invention 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] propionic acid derivatives correspond to the formula II

• N =* - *  .- -ι ♦

in which Y is a group -NR ¹⁶ R ¹⁷ , -O-R ¹⁸ , -SR ¹⁸ or -ON = CR ¹⁹ R ²⁰ , R ¹⁶ and R ¹⁷ independently of one another are hydrogen, C ₁ -C ₈ -alkoxy, C ₁ - C ₈ alkyl, phenyl or benzyl,

R ¹⁶ and R ¹⁷ together with their supporting nitrogen atom, a 5- to 6-membered saturated nitrogen heterocycle, the

may be interrupted by an oxygen or sulfur atom,

R ^{18 is} hydrogen or the equivalent of an alkali metal, alkaline earth metal, copper or iron ion; a quaternary Ci-C ₄ -alkylammonium or Crd-hydroxyalkylammonium radical; an optionally mono- or polysubstituted by amino, halogen, hydroxyl, cyano, nitro, phenyl, C ₁ -C ₄ -alkoxy, polyethoxy having 2 to 6 ethylene oxide units, -COOR ²¹ , -COSR ²¹ , -CONH ₂ -, -CON ( Ci-C ₄ alkoxy) -C-C ₄ alkyl, -CO-N-di-Ci-C ^ alky ^ -CONH-CrCvalkyl.-NFCRC ^ alkoxy-CrCj-alkyl or di-C _r C ₄ alkylamino substituted C _r C ₉ alkyl radical; a C ₃ -C ₉ -alkenyl radical optionally substituted by halogen or C ₁ -C ₄ -alkoxy; one

optionally substituted by halogen or Ci-C ₄ -Akoxy substituted C ₃ -C _g -Alkinylrest;

C ₃ -C ₉ cycloalkyl; or optionally substituted by cyano, C ₁ -C ₄ alkyl, C _r C ₄ alkoxy, acetyl, -COOR ^21, -COSR ^21, -CONH _2, -CON (C ₁ -C ₄ -

alkoxy) -C _r C ₄ alkyl, -C0-N-di-CrC ₄ alkyl or-CONH-Crd-alkyl substituted phenyl, R ¹⁹ and R ²⁰ independently of one another C ₁ -C ₄ -alkyl or together are a 3- to 6-membered alkylene chain and

R ²¹ is hydrogen, Ci-C ₆ -alkyl, Ci-Ce-haloalkyl, C ₂ -C ₆ -AlkoxyaIkyl, C ^ Ce-alkenyl, Cs-Ce-haloalkenyl, C ₃ -C ₆ -AIkJnYl or

Ca-Ce-haloalkynyl.

In the compounds of formula II, halo represents as an independent substituent or part of another substituent such as haloalkyl, haloalkoxy, haloalkenyl or haloalkynyl, fluoro, chloro, bromo or iodo, among which fluoro or chloro

are preferred.

Alkyl is, depending on the number of carbon atoms present, methyl, ethyl, n-propyl, i-propyl and the isomers butyl, P.entyl, hexyl, heptyl or octyl. The alkyl groups contained in the radicals alkoxy, alkoxyalkyl, haloalkyl or haloalkoxy have the same meaning. Preferred are each alkyl group with a low number of carbon atoms.

Preferred haloalkyl radicals or haloalkyl moieties in a haloalkoxy radical are: fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, trichloromethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, perfluoroethyl, 2-chloroethyl, 2,2, 2

Trichloroethyl, 2-bromoethyl and 1,1,2,3,3,3-hexafluoropropyl.

Cycloalkyl is mono- and bi-cyclic saturated hydrocarbon ring systems such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, bicyclo [4.3.0] nonyl, bicyclo [5.2.0] nonyl or bicyclo [2.2.2] octyl ,

Particularly noteworthy is the protective effect of Chi noli η derivatives of the formula I over such herbicides of the formula II, in which Y represents the groups -O-R ¹⁸ , -SR ¹⁸ , or -O-N = CR ¹⁹ R ²⁰ , wherein R ¹⁸ is hydrogen, C _r C ₄ -Alkkyl, C ₃ -C ₄ alkynyl or CRCI alkoxycarbonyl or di-CrC ₄ alkylamino-substituted C _r C ₄ alkyl and R ¹⁹ and R ²⁰ independently of one another

C ₁ -C ₄ -alkyl or R ¹⁹ and R ²⁰ together denote a CpCy-alkylene chain.

Particular noteworthy individual meanings for Y are methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, diethylaminoethoxy, propargyloxy, 1-cyano-1-methylethoxy, methoxycarbonylmethylthio, 1-ethoxycarbonylethoxy,

Butyloxycarbonyl, -ON = C (CH ₃ ) ₂ , -O-N = C (CH ₃ ) C ₂ H ₅ or-ON = C (CH ₂ ) ₅ .

The optically active carbon atom of the propionic acid group usually has both R and S configurations. Without particular mention herein is meant the racemic mixtures. Preferred herbicides of the formula II are 2R-configured.

Examples of herbicidally active 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid derivatives, against their action

Crop plants can be protected according to the invention are listed in Table 2 below.

Table 2:

-0-CH-CO-Y

(II)

No. Y -OCH ₃ physical constant 2.1 -0C, H ₉ -n Mp. 63-64 ⁰ C 2.2 -O-N = C (CH ₃ ) 2 ny ⁵ - 1.5275 2.3 -OC ₂ H ₅ n ^ ⁵ - 1.5488 2.4 -O-CH ₂ -CH ₂ -N (CH ₃ ) ₂ n ^ ⁵ = 1.5358 2.5 -O-CH ₂ -CsCH n ^ ⁵ ' 1.5334 2.6 -OC-CN CH ₃ CH ₃ n ^ ⁵ - 1.5492 2.7 -S-CH ₂ -COOCH ₃ n ^ ⁵ = 1.5330 2.8 -O-CH-COOC ₂ H ₅ CH ₃ n ^ ⁵ - 1.5607 2.9 -O-CH ₂ -COOC !, Hg-n n ^ ⁵ «= 1.5227 2.10 -OC ₃ H ₇ -n n ^ ⁵ - 1.5223 2.11 -OC ₃ H ₇ -I n ^ ⁵ = 1.5319 2.12 -0-N = CC ₂ H ₅ CH ₃ n ^ ⁵ = 1.5284 2.13 \ / * · - · n ^ ⁵ - 1.5340 2.14 -OCH ₃ (2R) n ^ ⁵ «1.5360 2.15 -OH n ^ ⁵ - 1.5359 2.16 -S-CH ₂ -COOCH ₃ (2R) Mp. 95-97 ° C 2.17 -O-CH-COOC ₂ H ₅ (2R, S) CH ₃ n ^ ⁵ - 1.5623 2.18 -O-CH ₂ -CsCH (2R) n ^ ⁵ - 1.5223 2.19 -NH-OCH ₃ Mp 55-56 ⁰ C 2.20 Mp. 103-105 ⁰ C

As crops which can be protected by quinoline derivatives of the formula I against damaging effects of herbicides of the formula II, especially those which are of importance in the food or textile sector, for example sugar cane and especially millet, corn, rice and other cereals come into consideration (Wheat, rye, barley, oats). Especially at this point is the use of wheat, rye, barley and rice

highlight.

A preferred embodiment of the process according to the invention consists in the use of isopropyl 2-quinoline-8-yloxyacetate, n-dodecyl 2- (5-chloroquinolin-8-yloxy) acetic acid, 2- (5-chloroquinolin-8-yloxy) n-Butyl acetate, 2- (5-chloro-quinolin-8-yloxy) -acetic acid-n-octyl ester, 2-quinolin-8-yloxy-acetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid n-octyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-butenyl) ester, 2- (5-chloroquinolin-8-yloxy) acetic acid methallyl ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid (2-isopropyloxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid - (1-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid cyclohexyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid s-butyl ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid (2-methylpentyl) ester, 2- (5-chloro-quinol-8-yloxy) -thioacetic acid n-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3, 6 dioxadecyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3-methoxybutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2 (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid n-undecyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid s-butyl ester , 2- (5-Chloroquinolin-8-yloxy) -acetic acid (3,6-dioxaheptyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-heptyl ester, 2- (5-chloroquinoline) 8-yloxy) -thioacetic acid n-dodecyl ester, 2- (5-chloro-quinolin-8-yloxy) thioacetic acid n-decyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propyl propargyl) ester , 2- (5-Chloroquinolin-8-yloxy) -acetic acid (1-methylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid tert -butyl ester, 2- (5-chloroquinoline-8- yloxy) acetic acid neopentyl ester, 2- (5-chloroquinoline-8'-yloxy) thioacetic acid n-propyl ester, Ethyl 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, 2- (5-chloro-quinolin-8-yloxy) thioacetate, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid i-butyl ester, 2-quinolin-8-yloxy-thioacetic acid n-decyl ester, 2- (5-chloroquinolin-8-yloxy ) -acetic acid i-pentyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) - 2- (5-chloroquinolin-8-yloxy) - 2- (5-chloroquinolin-8-yloxy) thioacetic acid esters, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-hexyl esters thioacetic acid i-propyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-pentylallyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1,1-dimethylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethyl-1-methylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid-n-butyloxycarbonylmethyl ester, 2- (5-chloro-ch inolin-8-yloxy) -acetic acid (1-n-butyloxycarbonylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinoline-8- yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-methyl-phenoxy) -ethyl] -ester, 2- ( 5-Chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester , 2- (5-Chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2 -isopropylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl] 2- (2-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) acetic acid [1-methyl-2- (3-ethylphenoxy) ethyl] ester, 2- (5- Chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester, 2- { 5-chloroquinolin-8-yloxy) acetic acid [1-methyl-2- (3-methylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) acetic acid [1-methyl-2- (4-isopropylphenoxy) ethyl] ester or 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester

for the protection of crops, in particular cereals, against the damaging effect of 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid methyl ester, ZW-fS-chloro-S-fluoropyridine ^ -xylxyl- Propergyl phenoxyl propionate, 2- [4- (5-chloro-3-fluoro-pyridin-2-yloxy) -phenoxy] -thiopropionic acid S-methoxycarbonylmethyl ester or 2- [4- (5-chloro-3-fluoropyridine-2-yl]

yloxyl-phenoxy-propionic acid-d äthoxycarbonyläthyll ester.

Because of the outstanding achievable result, the user will preferably use the compounds 2- (5-chloroquinolin-8-yloxy) acetic acid methallyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid 5-chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinoline-8- yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid ( 1-ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-pentylallyl) ester , 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5- Chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-äthylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid {1-methyl-2-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylpropyl) ester , 2- (5-Chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester or 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester

for protecting crops, especially cereals, against the deleterious effect of 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid methyl ester, 2- [4- (5-chloro-3-fluoropyridine -2-yloxy) -phenoxy] -propionic acid propargyl ester, 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -thiopropionic acid S-methoxycarbonylmethyl ester or 2- [4- (5-chloro-3-fluoropyridine -2-

Use yloxyj-phenoxyl-propionic acid-d-ethoxycarbonyläthylj-ester.

A suitable method for protecting crops using compounds of formula I is that crops, parts of these plants or soils for the cultivation of crops before or after the introduction of the plant material into the soil with a compound of formula I or an agent containing such a compound treated. The treatment may be before, simultaneously with, or after the use of the herbicide of formula II. Particularly suitable plant parts are those which are capable of regenerating a plant, such as, for example, seeds, fruits, stalk parts and twigs (cuttings) as well as roots, tubers and rhizomes.

The invention also relates to a method for the selective control of weeds in crops, wherein the crop stands, parts of crops or cultivated areas for crops with a herbicidal formula II and a compound of formula I or an agent comprising a combination of such a herbicide and a compound

of formula I, treated.

The present invention also relates to herbicidal compositions which are a combination of the antagonistic

Component I and the herbicidal component II.

Preferably such agents contain as antagonist component a compound from the series 2-quinoline-8-yloxy-isopropyl acetate, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-dodecyl ester, 2- (5-chloroquinolin-8-yloxy ) -acetic acid n-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid-n-octyl ester, 2-quinolin-8-yloxy-acetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy ) -thioacetic acid-n-octyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (2-butenyl) -ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid methallyl ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid (2-isopropyloxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) - acetic acid (1-methylbutyl) ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid cyclohexyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid s-butyl ester, 2- (5-chloro-orchinoline -8-yloxy) -acetic acid (2-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3 , 6- dioxadecyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3-methoxybutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2 (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid n-undecyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid s butyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (3,6-dioxaheptyl) ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid n-heptyl ester, 2- (5- Chloroquinolin-8-yloxy) thioacetic acid n-dodecyl ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid n-decyl ester, 2- (5-chloroquinolin-8-yloxy) acetic acid (1-propyl propargyl) ester, 2- (5-chloro-orchinolin-8-yloxy) -acetic acid (1-methylisobutyl) ester,

2- (5-Chloroquinolin-8-yloxy) thioacetic acid tert-butyl ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid neopentyl ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid-n- propyl,

2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester,

Ethyl 2- (5-chloroquinolin-8-yloxy) thioacetate, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid i-butyl ester, 2-quinolin-8-yloxy-thioacetic acid n-decyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid i-pentyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-hexyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid n-hexyl ester, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid i-propyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1 -pentylallyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1,1-dimethylpropargyl) - ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethyl-1-methylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid-n-butyloxycarbonylmethyl-ester, 2- (5-yloxy chloroquinolin-8) -acetic acid (1-n-butyloxycarbonyläthyl) ester, 2- (5-Chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid [1-methyl-2- (2-methyl-phenoxy) -ethyl] -ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) -ester, 2- (5-Chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl 2-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-isopropylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy ) -acetic acid (1-phenylpropyl) ester, 2- (5-chloroquinol-8-yloxy) -acetic acid [1-methyl-2- (2-ethylphenoxy) ethyl] ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid [1-methyl-2- (3-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) - ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2 ( 3-methylphenoxy) ethyl] ester, 2- (5- Chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-isopropylphenoxy) ethyl] ester or 2- (5-chloroquinolin-8-yloxy] -acetic acid [1-methyl-2- (4-methylphenoxy ) ethyl] ester and as a herbicidal component of a series

2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid methyl ester, 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid propargyl ester, 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -thiopropionsäure-S-methoxycarbonylmethylester

or 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) phenoxy] propionate (1-äthoxycarbonyläthyl) ester.

Particularly preferred among these agents are those which, as an antagonistic component, are the compounds

2- (5-chloroquinolin-8-yloxy) acetic acid methallyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) - ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-ethylpentyl) ester, 2- (5 -Chloroquinoline-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid- (1-pentylallyl (-ester, 2- (5-chloroquinolin-8-yloxy) ) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1 phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2 ( 4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- (5-chloro-quino lin-8-yloxy) -acetic acid (1-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester or 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester and as herbicidal component the compounds

Methyl 2- [4- (5-chloro-3-fluoropyridirid-2-yloxy) -phenoxy] -propionate, 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid propargyl ester, 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -thiopropionic acid S-methoxycarbonylmethyl ester or 2- [4- (5-chloro-3-fluoropyridin-2-yioxy) -phenoxy] - propionic acid (1-ethoxycarbonylethyl) ester.

Among these agents, preference is furthermore given to those compositions which contain the antagonist active ingredient 2- (5-chloroquinolin-8-yloxy) -acetic acid, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester , 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester or 2- (5-chloro-thchtolin-8-yloxy) -acetic acid (1-methylhexyl) ester.

The weeds to be controlled can be both monocotyledonous and dicotyledonous weeds.

Suitable crops or parts of these plants are, for example, those mentioned above. Areas under cultivation are areas of land already covered with crops or seeded with these crops,

as well as for the cultivation of these crops certain soils.

The application rate of antidote in relation to the herbicide depends largely on the type of application. In a field treatment, which is carried out using either a tank mix with a combination of antidote and herbicide or by separate application of antidote and herbicide, is usually a ratio of antidote to herbicide of 1: 100 to 10: 1, preferably 1:20 to 1: 1, and especially 1: 1, before. In contrast, in the seed dressing far

lower levels of antidote in relation to the application rate of herbicide per hectare of cultivated area needed.

In the field treatment, 0.01 to 10 kg of antidote / ha, preferably 0.05 to 0.5 kg of antidote / ha, are generally applied.

In seed dressing, 0.01 to 10 g of antidote / kg of seeds, preferably 0.05 to 2 g of antidote / kg of seed, are generally applied. If the antidote is applied in liquid form shortly before sowing with seed swelling, it is expedient to use antidote solutions which contain the active ingredient in a concentration of 1 to 10,000, preferably

from 100 to 1000 ppm.

For application, the compounds of the formula I or combinations of compounds of the formula I with the herbicides to be antagonized are expediently used together with the auxiliaries customary in formulation technology and are therefore used, for example. As to emulsion concentrates, spreadable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and encapsulations in z. B.

polymeric substances, processed in a known manner. The application methods such as spraying, atomizing, dusting, scattering, brushing or pouring are the same as the type of means to be used the desired objectives and the

given proportions chosen.

The formulations, d. H. the active ingredient of formula I or a combination of active ingredient of formula I with antagonizing herbicide and, optionally, a solid or liquid additive containing agent, preparations or compositions are prepared in known manner, e.g. by intimately mixing and / or grinding the active compounds with extenders, such as. As with solvents, solid carriers, and optionally surface-active

Compounds (surfactants).

Suitable solvents are: Aromatic hydrocarbons, preferably the fractions C ₈ to C ₁₂ , wiez. B.

Xylene or substituted naphthalenes, phthalic acid esters such as dibutyl or Dioctylphthalat, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters such as ethanol, ethylene glycol, ethylene glycol monomethyl or -äthyläther. Ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, and optionally epoxidized vegetable oils such as epoxidized

Coconut oil or soybean oil; or water.

As solid carriers, for. For example, for dusts and dispersible powders, natural minerals are generally used, such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties, it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. As granular, adsorptive granules are porous types such. As pumice, broken brick, sepiolite or bentonite, as non-sorptive support materials, eg. As calcite or sand, in question. In addition, a variety of pre-granulated materials of inorganic or organic nature, in particular dolomite or crushed plant residues can be used.

Depending on the nature of the compound of formula I to be formulated and optionally also the herbicide to be antagonized, surface-active compounds are nonionic, cationic and / or anionic surfactants with good emulsifying, dispersing

and network properties. Surfactants are also understood as meaning surfactant mixtures.

Suitable anionic surfactants may be both so-called water-soluble soaps and water-soluble synthetic surfactants

Be connections.

As soaps are the Al kali-, alkaline earth or optionally substituted ammonium salts of higher fatty acids (C ₁₀ -C ₂ 2), such as

z. As the Na or K salts of oleic or stearic acid, or of natural fatty acid mixtures, the z. B. from coconut or tallow

can be obtained, called. Furthermore, the fatty acid methyltaurine salts should be mentioned.

More often, however, so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated

Benzimidazole derivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are generally present as alkali, alkaline earth or optionally substituted ammonium salts and have an alkyl radical having 8 to 22C atoms, wherein alkyl also includes the alkyl moiety of acyl radicals, for. As the Na or Ca salt of lignin, the Dodecylschwefelsäureesters or one of natural fatty acids

Fatty alcohol sulfate mixture.

This subheading also covers the salts of sulfuric acid esters and sulfonic acids of fatty alcohol / ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2-sulfonic acid groups and a fatty acid residue having 8 to 22C atoms. Alkylarylsulfonates are z. As the Na, Ca orTriäthanolaminsalze of dodecylbenzenesulfonic acid, the

Dibutylnaphthalenesulfonic acid, or a naphthalenesulfonic acid-formaldehyde condensate product.

Furthermore, corresponding phosphates such. B. Salts of the Phosphoric Acid Ester of a p-Nonylphenol- (4-14) -

Ethylene oxide adduct or phospholipids in question.

Suitable nonionic surfactants are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, the 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols

can contain.

Further suitable nonionic surfactants are the water-soluble polyethylene oxide adducts containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups, polypropylene glycol, ethylene diaminopolypropylene glycol and alkyl polypropylene glycol having 1 to 10 carbon atoms in the alkyl chain. The compounds mentioned contain

usually 1 to 5 ethylene glycol units per propylene glycol unit.

Examples of nonionic surfactants are nonylphenolpolyäthoxyäthanole, Ricinusölpolyglykoläther, polypropylene Polyäthylenoxidaddukte, Tributylphenoxypolyäthoxyäthanol, polyethylene glycol and Octylphenoxypolyäthoxyäthanol

mentioned.

Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as the polyoxyethylene sorbitan trioleate.

The cationic surfactants are, above all, quaternary ammonium salts which, as N-substituents, are at least

contain an alkyl radical having 8 to 22C atoms and have as further substituents lower, optionally halogenated alkyl, benzyl or lower hydroxyalkyl radicals. The salts are preferably in the form of halides, methylsulfates or ethylsulfates, e.g. As the stearyltrimethylammonium chloride or Benzyldi (2-chloroethyl) ethyl ammonium bromide. The surfactants commonly used in formulation technology are i.a. described in the following publications:

Mc Cutcheon's Detergents and Emulsifiers Annual MC Publishing Corp., Ridgewood New Jersey, 1981

 Stäche, H., "Surfactant Paperback", Carl Hanser Verlag, Munich / Vienna, 1981.

The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula I or active ingredient mixture of antidote / herbicide, from 1 to 99.9% by weight, in particular from 5 to 99.8 Wt .-%, of a solid or liquid additive and 0 to 25 wt .-%, in particular 0.1 to 25Gew .-%, of a surfactant.

While merchandise tends to be more concentrated, the end user typically uses diluted ones

Medium.

The compositions may also contain other additives such as stabilizers, defoamers, viscosity regulators, binders, adhesives and fertilizers or other active ingredients to achieve special effects.

For the use of compounds of the formula I or compositions containing them for protecting crop plants against damaging effects of herbicides of the formula II, various methods and techniques are contemplated, such as

for example, the following:

i) seed dressing

a) seed dressing with a formulated as a wettable powder of formula I by shaking in a vessel until evenly distributed on the seed surface (dry dressing). It uses about 1 to 500 g of active ingredient of formula I (4g to 2 kg spray powder) per 100 kg of seed.

b) dressing the seeds with an emulsion concentrate of the active ingredient of the formula I according to the method a) (wet pickling).

c) pickling by dipping the seed in a broth containing 50-3200 ppm of active ingredient of the formula I for 1 to 72 hours and optionally subsequent drying of the seeds (immersion pickling).

The seed dressing or the treatment of the germinated seedling are by nature the preferred methods of administration because the treatment of the active ingredient is completely directed to the target crop. As a rule, 1 to 500 g of antidote, preferably 5 to 250 g of antidote, are used per 100 kg of seed, depending on the methodology which also permits the addition of other active substances or micronutrients, deviating upwards or downwards from the stated limiting concentrations

can (repeat pickle).

ii) Application from tank mix

A liquid work-up of a mixture of antidote and herbicide (mutual ratio between 10: 1 and 1: 100) is used, the application rate of herbicide being 0.1 to 10 kg per hectare. Such tank mix will happen

or applied after sowing.

iii) application in the seed furrow

The antidote is introduced as emulsion concentrate, wettable powder or granules into the open seeded seed furrow, and then, after covering the seed furrow, the pre-emergence herbicide is normally applied.

iv) Controlled drug delivery

The active ingredient of the formula I is applied in solution to mineral granules or polymerized granules (urea / formaldehyde) and allowed to dry. Optionally, a coating can be applied (coating granules), which allows dispensed dosed over a certain period of time.

embodiments Formulation example for liquid active substances of the formula I {% =% by weight)

1. Emulsion Concentrates a) b) O Active ingredient from Table 1 25% 40% 50% Calcium dodecylbenzenesulfonate 5% 8th% 6% Castor oil polyethylene glycol ether (36 moles of AeO) 5% - - Tributylphenol polyethylene glycol ether (30 moles of AeO) - 12% 4% cyclohexanone - 15% 20% xylenes 65% 25% 20%

From such concentrates, emulsions of any desired concentration can be prepared by dilution with water.

2. Solutions

Active substance from Table 1 Ethylene glycol monomethyl ether Polyethylene glycol MG 400 N-methyl-2-pyrrolidone Epoxidized coconut oil Gasoline (boiling limit 160-190 ⁰ C)

The solutions are suitable for use in the form of very small drops.

a) b) O d) 80% 10% 5% 95 ° / c 20% - - - - 70% - - - 20% - - - - 1% 5% _ 94%

3. Granules

Material from Table 1

kaolin

Highly dispersed silicic acid

attapulgite

a) b) 5% 10% 94% - 1%

90%

The active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the solvent is then evaporated in vacuo.

4. Dusts

Active substance from Table 1 Fumed silica Talc Kaolin

a) 2% 1% 97%

b)

90%

Intimately mixing the excipients with the active ingredient gives ready-to-use dusts. Formulation Examples of Solid Active Ingredients of Formula I (% = Wt.%)

5. Spray powder

Active ingredient of Table 1

Na ligninsulfonate

Na lauryl sulfate

Na Diisobutylnaphthalinsulfonat

Octylphenolpolyethylene glycol ether (7-8 moles of AeO) fumed silica

kaolin

a) b) c) 25% 50% 75% 5% 5% - 3% - 5% - 6% 10% - 2% - 5% 10% 10% 62% 27% _

The active ingredient is well mixed with the additives and ground well in a suitable mill. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration.

6. Emulsion Concentrates

Active ingredient of Table 1

Octylphenolpolyäthylenglykoläther (4-5 moles of AeO) Ca-dodecylbenzenesulfonate

Ricinus Polyglycol Ether (35 moles of AeO)

cyclohexanone

xylenes

From this concentrate emulsions of any desired concentration can be prepared by dilution with water.

7. Dust

Active ingredient of Table 1

talc

kaolin

b)

8th%

92%

Ready-to-use dusts are obtained by mixing the active ingredient with the excipients and grinding on a suitable mill.

8. extruder granules

Active ingredient Table 1 Na lignosulfonate carboxymethyl cellulose kaolin

The active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and then dried in a stream of air.

9. Serving Granules

Active ingredient Table 1 Polyethylene glycol (MW 200) Kaolin

The finely ground active substance is applied evenly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.

) b) O 5% 40% 50 ° / 5% 8th% 6 ° / 5% - _ - 12% 4 ° / < - 15% 20 ° / < 5% 25% 20 ° / <

10. suspension concentrates

Active substance from Table 1 40%

Ethylene glycol 10%

Nonylphenolpolyethylene glycol ether (15 molAeO) 6%

Na lignosulfonate 10% carboxymethyl cellulose 1%

37% aqueous formaldehyde solution 0.2%

Silicone oil in the form of a 75% aqueous emulsion 0.8%

Water 32%

The finely ground active ingredient is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.

Formulation example for active ingredient mixtures (liquid) (% =% by weight)

11. Emulsion Concentrates

Active ingredient mixture: Antidote from Table 1 and a herbicide of the formula II in the ratio 1: 1 Ca-dodecylbenzenesulfonate castor oil polyethylene glycol ether (36 moles of AeO) tributylphenol polyäthylenglykoläther (30 moles of AeO) cyclohexanone xylene mixture

From such concentrates, emulsions of any desired concentration can be prepared by dilution with water.

12. Emulsion Concentrates

Active ingredient mixture: Antidote from the table and a herbicide of the formula II in a ratio of 1: 3 Ca-dodecylbenzenesulfonate castor oil polyethylene glycol ether (36 moles of AeO) tributylphenol-polyäthylenglykoläther (30 moles of AeO) cyclohexanone xylene mixture

From such concentrates, emulsions of any desired concentration can be prepared by dilution with water.

13. Emulsion Concentrates a) b) c) Active substance mixture: Antidote from Table 1

and a herbicide of Formell II in a ratio of 2: 1 Ca-dodecylbenzenesulfonate castor oil polyethylene glycol ether (36 moles of AeO) tributylphenol polyethyleneglycol ether (30 moles of AeO) cyclohexanone xylene mixture

From such concentrates, emulsions of any desired concentration can be prepared by dilution with water. »

14. Emulsii ns Concentrates a) b) c) Active substance mixture: Antidote from Table 1

Methyl 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy-1-propionate in a 1: 1 ratio Ca-dodecylbenzenesulfonate castor oil polyethylene glycol ether (36 moles of AeO) tributylphenol-polyethyleneglycol ether (30 moles of AeO) cyclohexanone xylenes

From such concentrates, emulsions of any desired concentration can be prepared by dilution with water.

a) b) c) 25% 40% 50% 5% 8th% 6% 5% - _ - 12% 4% - 15% 20% 65% 25% 20%

25% 40% 50% 5% 8th% 6% 5% - - - 12% 4% - 15% 20% 65% 25% 20%

25% 40% 50% 5% 8th% 6% 5% - - - 12% 4% - 15% 20% 65% 25% 20%

25% 40% 50 ° / 5% 8th% 6 ° / c 5% - - - 12% 4 ° / < - 15% 20 ° / c 65% 25% 20 ° / c

15. Emulsion Concentrate a) b) c) Active substance mixture: AntidotausTabellei

and 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -

Phenoxyj-propionic acid methyl ester in the ratio 1: 3

Calcium dodecylbenzenesulfonate

Castor oil polyethylene glycol ether (36 MoI AeO)

Tributylphenol polyethylene glycol ether (30 moles of AeO)

cyclohexanone

xylenes

From such concentrates, emulsions of any desired concentration can be prepared by dilution with water.

16. Solutions a) b) c) d) Active substance mixture: AntidotausTabellei and a herbicide

1: 4 80% 10% 5% 95%

Ethylene glycol monomethyl ether 20% - - -

Polyethylene glycolMG400 - 70% - -

N-methyl-2-pyrrolidone - 20% - -

Epoxidized coconut oil - - 1% 5%

Gasoline (boiling limit 160-190 ⁰ C) - - 94% -

The solutions are suitable for use in the form of very small drops.

17. Solutions a) b) c) d) Active substance mixture: Antidote from Table 1 and a herbicide

the formallim ratio5: 2 80% 10% 5% 95%

Ethylene glycol monomethyl ether 20% - - -

Polyethylene glycolMG400 - 70% - -

N-methyl-2-pyrrolidone - 20% - -

Epoxidized coconut oil - - 1% 5%

Gasoline (boiling limit 160-190 ⁰ C) - - 94% -

The solutions are suitable for use in the form of very small drops.

18. Solutions a) b) c) d) Active substance mixture: Antidote from Table 1 and a herbicide

of the formula II in the ratio 1: 1 80% 10% 5% 95%

Ethylene glycol monomethyl ether 20% - - -

Polyethylene glycolMG400 - 70% - -

N-methyl-2-pyrrolidone - 20% - -

Epoxidized coconut oil - - 1% 5%

Gasoline (boiling limit 160-190 ⁰ C) - - 94% -

The solutions are suitable for use in the form of very small drops.

19. Solutions a) b) c) d) mixture of active ingredients: AntidotausTabellei and

2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] - 80% 10% 5% 95% methyl propionate in the ratio 1: 1

Ethylene glycol monomethyl ether 20% - - -

Polyethylene glycolMG400 - 70% - -

N-methyl-2-pyrrolidone - 20% - -

Epoxidized coconut oil - - 1% 5%

Gasoline (boiling limit 160-190 ⁰ C) - - 94% -

The solutions are suitable for use in the form of very small drops.

20. Solutions a) b) c) d) Active ingredient mixture: Antidote from Tables 1 and

2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] - 80% 10% 5% 95% methyl propionate in the ratio 1: 4

Ethylene glycol monomethyl ether 20% - - -

Polyethylene glycolMG400 - 70% - -

N-methyl-2-pyrrolidone - 20% - -

Epoxidized coconut oil - - 1% 5%

Gasoline (boiling limit 160-190 ⁰ C) - - 94% -

The solutions are suitable for use in the form of very small drops.

21. Granules a) b) Active substance mixture: Antidote from Table 1 and a herbicide Formula 1 in the ratio 1: 1 5% 10 ° / kaolin 94% - Highly dispersed silicic acid 1% - attapulgite - 90 ° / <

The active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the solvent is then evaporated in vacuo.

22. Granules a) b)

Active ingredient mixture: Antidote from Table and 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -

methyl phenoxyl-propionate 5% 10%

in the ratio 1: 1

Kaolin - 94% -

Highly disperse silica 1% -

Attapulgite - 90%

The active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the solvent is then evaporated in vacuo.

23. Dusts a) b)

Active substance mixture: AntidotausTabellei

and a herbicide of formula II in 2% 5%

Ratio 1: 1

Highly disperse silica 1% 5%

Talc 97% -

Kaolin - 90%

Intimately mixing the excipients with the active ingredient gives ready-to-use dusts.

Formulation Examples of Active Ingredient Mixtures (Solid) {% = Wt.%)

24. Spray powder

Active ingredient mixture: AntidotausTabellei and a herbicide of the formula II in the ratio 1: 1 Na lignin sulfonate Na lauryl sulfate Na diisobutyl naphthalene sulfonate Octylphenolpolyäthylenglykoläther (7-8 mol AeO) fumed silica kaolin

The active ingredient is well mixed with the additives and ground well in a suitable mill. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration.

25. Spray powder

Active substance mixture: Antidote from the table and a herbicide of the formula II in the ratio 1: 4 Na lignosulfonate Na lauryl sulfate Na diisobutylnaphthalenesulfonate Octylphenolpolyethylene glycol ether (7-8 mol AeO) Highly disperse silica Kaolin

The active ingredient is well mixed with the additives and ground well in a suitable mill. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration.

a) b) O 25% 50% 75 ° / i 5% 5% 3% - 5 ° / c - 6% 10 ° / < - 2% - 5% 10% 10 ° / < 62% 27%

a) b) c) 25% 50% 75 ° / 5% 5% 3% - 5 ° / t - 6% 10 ° / c - 2% - 5% 10% 10 ° / " 62% 27%

a) b) -72- 261734 O 26. Spray powder Active substance mixture: Antidote table 1 25% 50% 75% and a herbicide of the formula II in the Verhältnis3: 1 5% 5% - Na ligninsulfonate 3% - 5% Na lauryl sulfate - 6% 10% Na Diisobutylnaphthalinsulfonat - 2% - Octylphenolpolyethylene glycol ether (7-8 moles of AeO) 5% 10% 10% Highly dispersed silicic acid 62% 27% kaolin

The active ingredient is well mixed with the additives and ground well in a suitable mill. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration.

27. Emulsion Concentrates Active substance mixture: Antidote Table 1 and a herbicide of the formula II in the ratio 1: 1 Octylphenolpolyäthylenglykoläther (4-5 moles of AeO) Ca-dodecylbenzenesulfonate Ricinusölpolyglykoläther (35MolAeO) cyclohexanone

xylenes

10%

3% 3% 4% 30% 50%

From this concentrate emulsions of any desired concentration can be prepared by dilution with water.

28. Emulsion Concentrates Active substance mixture: Antidote Table 1 and a herbicide of the formula II in a ratio of 5: 2 octylphenolpolyethylene glycol ether (4-5 moles of AeO) Ca-dodecylbenzenesulphonate castor oil polyglycol ether (35 moles of AeO) cyclohexanone

xylenes

10% 3% 3% 4% 30% 50%

From this concentrate emulsions of any desired concentration can be prepared by dilution with water.

29. Emulsion Concentrates Active substance mixture: Antidote from Table 1 and a herbicide of the formula II in the ratio 1: 4 Octylphenolpolyäthylenglykoläther (4-5 moles of AeO) Ca-dodecylbenzenesulfonate Ricinusölpolyglykoläther (35 moles of AeO) cyclohexanone

xylenes

10% 3% 3% 4% 30% 50%

From this concentrate emulsions of any desired concentration can be prepared by dilution with water.

a) b)

30. Dusts Active substance mixture: Antidote from Table 1 and a herbicide of the formula II in the ratio 1: 1 talcum kaolin

5% 95%

8th%

92%

Ready-to-use dusts are obtained by mixing the active ingredient with the excipients and grinding on a suitable mill.

31. Extruder Granules Active ingredient mixture: Antidote Table 1 and a herbicide of the formula II in the ratio 1: 1 Na Liginsulfonate Carboxymethylcellulose Kaolin

10% 2% 1% 87%

The active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and then dried in a stream of air.

32. Envelope Granules Mixture of Active Substances: Antidote Table 1 and a Herbicide of Formula II in the Ratio of 1: 1 Polyethylene Glycol (MG200)

3% 3%

The finely ground active substance is applied evenly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.

33. suspension concentrates

Active substance mixture: Antidote from Table 1 and

a herbicide of formula II in the ratio 1: 1 40%

Ethylene Glycol 10% Nonylphenol Polyethylene Glycol Ether (15 moles AeO) 6%

Na lignin sulphonate 10% carboxymethylcellulose 1%

37% aqueous formaldehyde solution 0.2%

Silicone oil in the form of a 75% aqueous emulsion 0.8%

Water 32%

The finely ground active substance is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.

34. Suspension concentrates

Active substance mixture: AntidotausTabellei and

a herbicide of formula II in the ratio 1: 4 40%

Ethylene Glycol 10% Nonylphenol Polyethylene Glycol Ether (15 moles AeO) 6%

Na lignosulfonate 10% carboxymethyl cellulose 1%

37% aqueous formaldehyde solution 0.2%

Silicone oil in the form of a 75% aqueous emulsion 0.8%

Water 32%

The finely ground active substance is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.

35. suspension concentrates

Active ingredient mixture: Antidotex Table 1 and

a herbicide of the formula brain ratio 3: 1 40%

Ethylene glycol 10%

Nonylphenolpolyethylene glycol ether (15 moles of AeO) 6%

Na lignosulphonate 10%

Carboxymethylcellulose 1%

37% aqueous formaldehyde solution 0.2%

Silicone oil in the form of a 75% aqueous emulsion 0.8%

Water 32%

The finely ground active substance is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.

Biological examples Test description

In the greenhouse, plastic pots containing 0.51% soil are fed with seeds from the plants to be tested. When the plants have reached the 2- to 3-leaf stage, a safener of formula I and a herbicide of formula II are applied together as a tank mix. 21 days after application, the protective effect of the safener is rated in percent. The reference used here are plants treated with the herbicide alone and the completely untreated control. The results are shown in Table 3 below.

Table 3:

Relative percentage protection in summer wheat, variety "Besso" and spring barley, variety "Cornel"

Expenditure- herbicide Expenditure- relative relative safener No. protection protection Verb.Nr quantity g AS / ha 2.1 quantity g AS / ha in wheat in% in barley in% 1125 31 2.1 125 10 30 1125 62 2.1 125 0 25 1125 125 2.1 125 10 30 1125 62 2.1 250 70 15 1125 125 2.1 250 65 25 1125 250 2.1 250 65 15 1125 125 2.1 500 80 13 1125 250 2.1 500 75 8th 1125 500 2.6 500 75 18 1125 31 2.6 125 20 60 1125 62 2.6 125 20 70 1125 125 2.6 125 20 65 1125 62 2.6 250 50 45 1125 125 2.6 250 55 50 1125 250 2.6 250 50 45 1125 125 2.6 500 70 35 1125 250 2.6 500 70 45 1125 500 2.8 500 65 35 1125 31 2.8 125 0 35 1125 62 2.8 125 0 35 1125 125 2.8 125 0 30 1125 62 2.8 250 10 45 1125 125 2.8 250 5 45 1125 250 2.8 250 10 30 1125 125 2.8 500 40 40 1125 250 2.8 500 40 40 1125 500 2.9 500 35 35 1125 31 2.9 125 10 65 1125 62 2.9 125 15 60 1125 125 2.9 125 15 75 1125 62 2.9 250 50 60 1125 125 2.9 250 45 55 1125 250 2.9 250 30 60 1125 125 2.9 500 75 50 1125 250 2.9 500 65 45 1125 500 500 65 45

Table 3 (continued)

Expenditure- herbicide Expenditure- relative relative safener No. protection protection Verb.Nr Tnenge g AS / ha 2.1 mcHgö g AS / ha in wheat in% in barley in% 1130 31 2.1 125 5 5 1130 62 2.1 125 10 5 1130 125 2.1 125 0 5 1130 62 2.1 250 70 0 1130 125 2.1 250 60 0 1130 250 2.1 250 70 0 1130 125 2.1 500 70 8th 1130 250 2.1 500 75 8th 1130 500 2.6 500 80 8th 1130 31 2.6 125 15 5 1130 62 2.6 125 20 5 1130 125 2.6 125 20 5 1130 62 2.6 250 65 0 1130 125 2.6 250 65 0 1130 250 2.6 250 65 0 1130 125 2.6 500 65 0 1130 250 2.6 500 75 0 1130 500 2.8 500 80 0 1130 31 2.8 125 0 15 1130 62 2.8 125 0 0 1130 125 2.8 125 0 0 1130 62 2.8 250 15 5 1130 125 2.8. 250 15 0 1130 250 2.8 250 5 5 1130 125 2.8 500 40 0 1130 250 2.8 500 40 0 1130 500 2.9 500 40 0 1130 31 2.9 125 15 35 1130 62 2.9 125 15 35 1130 125 2.9 125 15 40 1130 62 2.9 250 50 5 1130 125 2.9 250 50 10 1130 250 2.9 250. 45 10 1.Ϊ30 125 2.9 500 55 5 1130 250 2.9 500 60 5 1130 500 500 70 5

Table 3 (continued)

Expenditure- herbicide Expenditure- relative relative safener No. · protection protection Verb.Nr quantity g AS / ha 2.1 g AS / ha in wheat in% in barley in% 1134 31 2.1 125 10 35 1134 62 2.1 125 10 45 1134 125 2.1 125 5 45 1134 62 2.1 250 75 20 1134 125 2.1 250 70 15 1134 250 2.1 250 65 15 1134 125 2.1 500 80 8th 1134 250 2.1 500 75 · 8th 1134 500 2.6 • 500 70 13 1134 31 2.6 125 20 45 1134 62 2.6 125 15 55 1134 125 2.6 125 20 65 1134 62 2.6 250 60 45 1134 125 2.6 250 60 50 1134 250 2.6 250 65 50 1134 125 2.6 500 90 20 1134 250 2.6 500 90 20 1134 500 2.8 500 80 15 1134 31 2.8 125 5 45 1134 62 2.8 125 0 45 1134 125 2.8 125 Ö 40 1134 62 2.8 250 10 50 1134 125 2.8 250 10 45 1134 250 2.8 250 10 40 1134 125 2.8 500 40 30 1134 250 2.8 500 35 30 1134 500 2.9 500 35 30 1134 31 2.9 125 20 65 1134 62 2.9 125 20 65 1134 125 2.9 125 20 60 1134 62 2.9 250 45 45 1134 125 2.9 250 50 60 1134 250 2.9 250 45 55 1134 125th 2.9 500 70 40 1134 250 2.9 500 .JO 40 1134 500 500 70 55

Table 3 (continued)

Expenditure- herbicide Expenditure- relative relative safener No. protection protection Verb.Nr quantity g AS / ha 2.1 quantity g AS / ha in wheat in% in barley in% ^: 1.186 31 2.1 125 10 45 i 1,186 62 2.1 125 - 15 35 1186 125 2.1 125 15 45 ; ' 1186 62 2.1 250 75 15 r 1,186 125 2.1 250 65 20 , 1.186 250 2.1 250 70 15 ', 1.186 125 2.1 500 85 13   1186 250 2.1 500 85 13 1186 500 2.6 500 75 13 f 1,186 31 2.6 125. 20 50 : 1.186 62 2.6 125 20 60 i 1,186 125 2.6 125 20 60 ^; 1186 62 2.6 250 50 35 1186 125 2.6 250 55 45. 1186 250 2.6 250 55 50 1186 125 2.6 500 90 25 I "1.186 250 2.6 500 85 20 ! 1186 500 2.8 500 70 20 1186 31 2.8 125 0 35 1186 62 2.8 125 0 45 1186 125 2.8 125 0 35 1186 62 2.8 250 0 35 1186 125 2.8 250 0 45 1186 250 2.8 250 0 40 1186 125 2.8 500 35 25 1186 250 2.8 500 35 25 1186 500 2.9 500 25 25 1186 31 2.9 125 20 40 1186 62 2.9 125 20 65 1186 125 2.9 125 20 60 1186 62 2.9 250 50 35 1186 125 2.9 250 40 45 1186 250 2.9 250. 50 55 1186 125 2.9 500 70 40 1186 250 2.9 500 60 • v5 1186 500 500 55 50

Table 3 (continued)

Expenditure- herbicide Expenditure- relative relative safener No. Vl \ ^^ 4 ^ f * F ^^ protection protection Verb.Nr quantity g AS / ha 2.1 quantity g AS / ha in wheat in% in barley in% 1188 31 2.1 125 15 15 1188 62 2.1 125 15 25 1188 125 2.1 125 15 30 1188 62 2.1 250 70 15 1188 125 2.1 250 70 15 1188 250 2.1 250 60 15 1188 125 2.1 _ 500 90 13 1188 250th 2.1 500 85 8th 1188 500 2.6 500 80 8th 1188 31 2.6 125 20 55 1188 62 2.6 125 20 50 1188 125 2.6 125 20 55 1188 62 2.6 250 65 30. 1188 125 2.6 250 65 50 1188 250 2.6 250 60 50 1188 125 2.6 500 85 20 1188 250 2.6 500 85 30 1188 500 2.8 500 80 30 1188 31 2.8 125 5 50 1188 62 2.8 125 5 55 1188 125 2.8 125 0 50 1188 62 2.8 250 10 65 1188 125 2.8 250 10 60 1188 250 2.8 250 10 60 1188 125 2.8 500 30 35 1188 250 2.8 500 30 35 1188 500 2.9 500 35 30 1188 31 2.9 125 20 50 1188 62 2.9 125 20 55 1188 125 2.9 125 20 50 1188 62 2.9 250 50 50 1188 125 2.9 250 50 45 1188 250 2.9 250 45 40 1188 125 2.9 500 75 30 1188 250 2.9 500 70 40 1188 500 500 75 40

Table 3 (continued)

Expenditure- herbicide Expenditure- relative relative safener No. protection protection Verb.Nr quantity g AS / ha 2.1 "amount AS / ha in wheat in%. in barley in% 1245 250 2.1 500 70 _ 1245 500 2.1 500 65 - 1245 250 2.1 1000 50 - 1245 500 2.8 1000 45 - 1245 62 2.8 250 55 50 1245 125 2.8 250 65 55 1245 125 2.8 500 75 58 1245 250. 2.1 500. 90 48 1247 250 2.1 500 65 - 1247 500 2.1. 500 75 - 1247 250 2.1 1000 45th - 1247 500 2.8 1000 65 - 1247 62 2.8 250 70 , - 1247 125 2.8 250 70 - 1247 125 2.8 500 80 - 1247 250 2.1 500 80 - α. 248 250 2.1 500 65 1248 500 2.1 500 65 - L 2 48 250 2.1 1000 40 - .1..248 500 2.8 1000 50 - 1248 62 2.8 250 70 60 1248 125 2.8 250 70 75 1248 125 2.8 500 90 68 1248 250 2.8 500 90 73 1255 62 2.8 250 _ 70 1255 125 2.8 250 - 70 1255 125 2.8 500 - 35 1255 250 2.1 500 - 50 1256 250 2.1 500 65 1256 500 2.1 500 65 - 1256 250 2.1 1000 60 - 1256 500 2.8 1000 50 - 1256 62 2.8 250 60 65 1256 125 2.8 , 250 65 60 1256 125 2.8 500 85 43 1256 250 500 80 73

Table 3 (continued)

O O ί ΛΤΊ Λ «" Expenditure- herbicide Expenditure- relative relative oarener No. φηη ^^ ^^ ^ V ^^ protection protection Verb.Nr quantity g AS / ha 2.8 quantity g AS / ha in wheat in% in barley in% 1259 62 2.8 250 _ 60 1,259. 125 2.8 250 - · · 75 1.259 · 125 2.8 500 - 53 1259 250 2.8 500 , - 68 1260 62 2.8 250 _ 65 1260 125 2.8 250 -. 60 1260 125 2.8 500 - 53 1260 250 2.8 500 - 53 1261 62 2.8 250 _ 65 1261 125 2.8 250 - 70 1261 125 2.8 500 - 58 1261 250 2.8 500 - 68 1262 62 2.8 250 _ 75 1262 125 2.8 250 - 85 1262 125 2.8 500 - 63 1262 250 2.1 500 - 78 1267 250 2.1 500 65 _ 1267 500 2.1 500 65 - 1267 250 2.1 -1000 55 - 1267 250 · 2.8 1000 50 - 1267 62 2.8 250 65 65 1267 125 2.8 250 65 70 1267 125 2.8 500 85 48 1267 250 2.1 500 85 73 1276 250 2.1 500 60 1276 500 2.1 500 55 - 1276 250 2.1 1000 * 35 - 1276 500th 2.8 1000 50 - 1276 62 2.8 250 70 65 1276 125 2.8 250 65 75 1276 125 2.8 500 85 63 1276 250 500 80 68

Table 3 (continued)

Expenditure- herbicide Expenditure- relative relative safener No. Ύΐν «* ^ T ^ rf ^ ^^ protection protection Verb.Nr quantity g AS / ha 2.1 quantity g AS / ha in wheat in% in barley in% 1284 250 2.1 500 60   _ 1284 500 2.1 500 65 - 1284 250 2.1 1000 50 i 1 * 284 500 2.8 1000 45 - 1284 62 2.8. 250 70 60 1284 125 2.8 250 65 55 1284 125 2.8 500 75 63 1284 250 2.1 500 70 73 1285 250 2.1 500 55 - 1285 500 2.1 500 65 - .1.285 250 2.1 1000 40 · - 1285 500 2.8 1000 50 - 1285 62 2.8 250 65 65 1285 125 2.8 250 65 65 1285 125 2.8 500 80 68 1285 250 2.1 500 85 78 1290 250 2.1 500 60 _. 1290 500 2.1 500 60 - 1290 250 2.1 1000 45 - 1290 500 2.8 1000 60 - L 290 62 2.8 250 50 70 1290 125 2.8 250 65 75 1290 125 2.8 500 80 63 1290 250 2.1 500 85 73 1293 250 2.1 500 60 _ 1293 500 2.1 500 45 - 1293 250 2.1 1000 45 - 1293 500 2.8 1000 70 - 1293 62 2.8 250 50 60 1293 125 2.8 250 55 65 1293 125 2.8 500 55 48 1293 250 500 80 53

Table 3 (continued)

expenditure herbicide Expenditure- relative relative safener No. protection protection Verb.Nr quantity g AS / ha 2.1 ugege AS / ha in wheat in% in barley in% 1301 250 2.1 500 70 _ 1301 500 2.1 500 75 - 1301 250 2.1 1000 50 - 1301 500 2.8 1000 45 - 1301 62 2.8 250 60 1301 125 2.8 250 65 - 1301 125 2.8 500 70 - 1301 250 2.8 500 75 - 1305 62 2.8 250 - 65 1305 125 2.8 250 - 70 1305 125 2.8 500 - 68 1305 250 2.8 500 - 73 1308 62 2.8 250 _ 90 1308 125 2.8 250 - 90 1308 125 2.8 500 - 1 63 1308 250 2.8 500 - 73 1314 62 2.8 250 _ 80 1314 125 2.8 250 - 90 1314 125 2.8 500 - 58 1314 250 2.1 500 - 63 1316 250 2.1 500 65 1316 500 2.1 500 65 - 1316 250 2.1 1000 35 - 1316 500 2.8 1000 50 - 1316 62 2.8 250 _ 50 1316 125 2.8 250 - 50 1316 125 2.8 500 - 55 1316 250 2.8 500 - 60 1321 62 2.8 250 _ 65 1321 125 2.8 250 - 80 1321 125 2.8 500 - 60 1321 250 2.1 500 - 70 1325 250 2.1 500 60 _ 1325 500 2.1 500 50 - 1325 250 2.1 1000 50 - 1325 500 1000 70 -

Table 3 (continued)

Expenditure- herbicide Expenditure- relative relative safener No. «Vt ^ \ *% ^ v ^^ protection Schutzwxrkung Verb.Nr quantity g AS / ha 2.8 quantity g AS / ha in wheat in% in barley in% 1327 62 2.8 250 - 70 1327 125 2.8 250 - 80 1327 125 2.8 500 - 50 1327 250 2.1 500 - 50 1333 250 2.1 500 63 _ 1333 500 2.1 500 73 - 1333 250 2.1 1000 35 - 1333 500 2.8 1000 55   - 1334 62 2.8 250 _ 75 1334 125 2.8 250 - 85 1334 125 2.8 500 - 63 1334 250 2.1 500 - 63 1336 250 2.1 500 70 _ 1336 500 2.1 500 75 - 1336 250 2.1 1000 45 - 1336 500 2.8 1000 45 - 1336 62 2.8 250 65 60 1336 125 2.8 250 65 60 1336 125 2.8 500 85 53 1336 250 2.1 500 85 23 1337 250 2.1 500 60 _ 1337 500 2.1 500 55 - 1337 250 2.1 1000 45 - 1337 500 2.8 1000 50 - 1337 62 2.8 250 65 65 1337 125 2.8 250 55 50 1337 125 2.8 500 70 63 1337 250 2.1 500 60 78 1341 250 2.1 500 58 _ 1341 500 2.1 500 73 - 1341 250 2.1 1000 25 - 1341 500 2.8 1000 60 - 1341 62 2.8 250 _ 90 * 1341 125 2.8 250 - 90 1341 125 2.8 500 - 63 1341 250 500 - 68

Table 3 (continued)

Expenditure- herbicide Expenditure- relative relative safener No. protection protection Verb.Nr g AS / ha 2.8 g AS / ha in wheat in% in barley in% 1353 62 2.8 250 _ 65 1353 125 2.8 250 - 75 1353 125 2.8 500 - 65 1353 250 2.1 500 - 60 1355 250 2.1 500 78 _ 1355 500 2.1 500 78 - 1355 250 2.1 1000 45 - 1355 500 2.8 1000 55 - 1355 62 2.8 250 50 _ 1355 125 2.8 250 55 - 1355 125 2.8 500 45 - 1,355. 250 " 2.8 500 55 - 1362 62 2.8 250 _ 90 1362 125 2.8 250 - 90 1362 125 2.8 500 - 63 1362 250 2.8 500 - 73 1363 62 2.8 250 _ 80 1363 125 2.8 250 - 80 1363 125 2.8 500 - 63 1363 250 500 - 63

-: not tested.

Claims (32)

1. A method for protecting crops against harmful effects herbicidally active 2- [4- (5-chloro-3-fluoro-pyridin-2-yloxy) -phenoxy] propionic acid derivatives of the formula II / - /, - f 3 Cl * '\ -O- / ^ - O-CH-CO-Y (H), in which Y represents a group -NR ¹⁶ R ¹⁷ , -OR ¹⁸ , -SR ¹⁸ or -O-N = CR ¹⁹ R ²⁰ , R ¹⁶ and R ¹⁷ independently of one another are hydrogen, C 1 -C ₈ -alkoxy, C ₈ -AlkVl, phenyl or benzyl, R ¹⁶ and R ¹⁷ together with the supporting nitrogen atom, a 5- to 6-membered saturated nitrogen heterocycle which may be interrupted by an oxygen or sulfur atom, R ^{18 is} hydrogen or the equivalent of an alkali metal, alkaline earth metal , Copper or iron ions; a quaternary dd-alkylammonium or d-C ^ hydroxyalkylammonium radical; an optionally mono- or polysubstituted by amino, halogen, hydroxyl, cyano, nitro, phenyl, C ₁ -C ₄ -alkoxy, polyethoxy having 2 to 6 ethylene oxide units, -COOR ²¹ , -COSR ²¹ , -CONH ₂ -, -CON ( C ₁ -C ₄ alkoxy) -C-C ₄ alkyl, -CO-N-di-dC ^ alkyl, -CONH-C ₁ - C ₄ alkyl, ^ (C ^ C ^ alkyl ^ or alkoxyJ-CiC _{di-Ci-C4-alkylamino-substituted} Ci-C ₉ alkyl group; an optionally substituted by halogen or Ci-C ₄ alkoxy substituted C ₃ -C ₉ -AlkenyIrest; an optionally substituted by halogen or C ₁ -C ₄ -alkoxy C C ₃ -C ₉ alkynyl radical; C ₃ -C ₉ cycloalkyl; or optionally substituted by cyano, dC ₄ alkyl, Ci-C ₄ -alkoxy, acetyl, -COOR ^21, -COSR ^21, -CONH _2, -CON (C ₁ -C ₄ alkoxy) -C ₁ -C ₄ alkyl , -CO-N-di-Ci-C ₄ alkyl or-CONH-C ₁ -C ₄ alkyl substituted phenyl, R ¹⁹ and R ²⁰ are independently Ci-C ₄ alkyl or together form a 3- to 6-membered alkylene chain and R ²¹ is hydrogen, dC ₆ alkyl, Cr-Ce-haloalkyl, Cr-Ce-Alkoxyalkkyl, C ₃ -C ₆ alkenyl , Cs-Cfä-haloalkyl, C ₃ -C ₆ -alkynyl or Cs-Ce-haloalkynyl, characterized in that the crops, parts of these plants or for the cultivation of crops certain soils with a compound of formula I. ^r3 "4-R ² I ^S I! I in. G-A-Z _R 6 in which R ¹ , R ² and R ³ independently of one another denote hydrogen, halogen, nitro, cyano, C ₁ -C ₃ -alkyl or C ₁ -C ₃ -alkoxy, R ⁴ , R ⁵ and R ^6, independently of one another, denote hydrogen, halogen or C ₃ alkyl, A is one of the groups -CH ₂ -, -CH ₂ -CH ₂ - or -CH (CH ₃ ) - and Z is cyano or amidoxime, which may be acylated on the oxygen atom, a carboxyl group or a salt thereof, a Mercaptocarbonyl group or a salt thereof, a carboxylic acid ester group, a carbonyl thioester group, an unsubstituted or substituted carboxamide group, a cyclized, unsubstituted or substituted derivative of a carboxylic acid amide group or a carboxylic acid hydrazide group or A and Z together represent an unsubstituted or substituted tetrahydrofuran-2-one ring, including their acid addition salts and metal complexes, or an agent containing one of these compounds. 2. The method of item 1, characterized in that a compound of formula I, in which R ^1, R ² and R ³ are independently hydrogen, halogen, nitro, cyano, Ci-C ₃ alkyl or C ₁ -C ₃ is -alkoxy, R ⁴ , R ⁵ and R ⁶ independently of one another are hydrogen, halogen or C ₁ -C ₃ -alkyl, A is -CH ₂ -, -CH ₂ -CH ₂ - or -CH (CH ₃ ) - and Z is cyano the groups -C (NH ₂ ) = N- OH or-C (NH ₂ ) = NO-CO-E is an optionally substituted oxazoline ^ -yl radical COOR ¹² , -COSR ¹³ or -CONR ¹⁴ R ¹⁵ wherein
E is -R ⁷ , -OR ⁸ , -SR ⁹ or -NR ¹⁰ R ¹¹ wherein R ^{7 is} C ₁ -C ₇ -alkyl which is unsubstituted or substituted by halogen or C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -cycloalkyl, C ₂ -C ₄ -alkenyl, phenyl which is unsubstituted or halogen, nitro or C ₁ -C ₃ -AlkYl substituted. Benzyl which is unsubstituted or substituted by halogen, nitro or C ₁ -C ₃ alkyl, or a 5- to 6-membered heterocyclic ring containing one or two heteroatoms from the group N, O and S and is unsubstituted or substituted by halogen . R ⁸ , R ⁹ and R ¹⁰ independently of one another are C ₁ -C ₈ -alkyl which is unsubstituted or substituted by halogen, C ₂ -C ₄ -alkenyl, C ₃ -C ₆ -alkynyl, phenyl which is unsubstituted or halogen, C ₁ -C ₃ -alkyl, C ₁ -C ₃ -alkoxy, trifluoromethyl or nitro, or benzyl which is unsubstituted or substituted by halogen or nitro, R ^{11 is} hydrogen, C ₁ -C ₈ -alkyl or C ₁ - C ₃ -alkoxy or R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached, a 5- to 6-membered heterocycle, which may contain a further heteroatom from the group N, O and S, R ¹² , R ¹³ and R ^{14 is} hydrogen or a optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or naphthyl radical or an optionally substituted heterocyclic radical or R ¹² and R ^{13 is} also a cation or R ^{14 is} also an alkoxy radical and R ^{15 is} hydrogen, amino, mono- or disubstituted . Amino or an optionally substituted alkyl, alkenyl, cycloalkyl or phenyl radical or R ¹⁴ and R ¹⁵ together with the nitrogen atom to which they are attached, an optionally substituted heterocyclic radical, or A and Z together represent an optionally substituted Tetrahydrofuran-2-one ring, including their acid addition salts and metal complexes, or an agent containing one of these compounds. 3. The method according to item 1, characterized by reacting a compound of formula I in which R ¹ , R ² , R ⁴ , R ⁵ and R ^{6 is} hydrogen, R ^{3 is} hydrogen or chlorine and the radical AZ for a Group -CH ₂ -COOR ¹⁶ or -CH (CH ₃ ) -COOR ¹⁶ in which R ^{16 is} C ₁ -C ₁₂ -alkyl, C ₃ -C ₆ -alkenyl, phenyl-C ₁ -C ₄ -alkyl or phenoxy-C ^ C ^ alkyl stands. 4. The method according to item 1, characterized in that 2-quinolin-8-yloxy-isopropyl acetate, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-dodecyl ester, 2- (5-chloroquinolin-8-yloxy ) -acetic acid n-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid-n-octyl ester, 2-quinolin-8-yloxy-acetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy ) -thioacetic acid-n-octyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (2-butenyl) -ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid methallyl ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid (2-isopropyloxyäthy!) Ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) acetic acid (1-methylbutyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid cyclohexyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid s-butyl ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid (2-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3, 6-dioxadecyl) ester, 2- (5-chloroquinoline 8-yloxy) -acetic acid (3-methoxybutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid - (2-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-undecyl ester, 2 - (5-chloroquinolin-8-yloxy) -acetic acid (2-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3,6-dioxaheptyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-heptyl ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-dodecyl ester, 2 - (5-chloroquinolin-8-yloxy) -thioacetic acid n-decyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylpropargyl) ester, 2- (5-Chloroquinolin-8-yloxy) -acetic acid (1-methylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid tert -butyl ester, 2- (5-chloroquinolin-8-yloxy ) acetic acid neopentyl ester, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid n-propyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid {1-methylhexyl) ester, 2- (5 Chloroquinolin-8-yloxy) thioacetic acid ethyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid i-butyl ester, 2-Quinolin-8-yloxy-thioacetic acid n-decyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid i-pentyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylpentyl ) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-hexyl ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid n-hexyl ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid i-propyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-pentylallyl) - ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpent yl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1,1-dimethylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethyl-1-) methylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-butyloxycarbonylmethyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-n-butyloxycarbonylethyl) ester, 2 - (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid Chloroquinolin-8-yloxy) acetic acid [1-methyl-2- (2-methyl-phenoxy) -ethyl] -, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) - ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1 -methyl-2-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-isopropylphenoxy) ethyl] ester, 2- (5-chloroquinoline-8 -yloxy) -acetic acid (1-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -8-acetic acid [1-methyl-2- (2-ethylphenoxy) ethyl] ester, 2- (5 -Chlorchinoli n-8-yloxy) -acetic acid [1-methyl-2- (3-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2- {5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester, 2 "(5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (3-methylphenoxy) ethyl] - ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-isopropylphenoxy) ethyl] ester or 2- (5-chloroquinoline) 8-yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester or an agent containing one of these compounds. 5. Method according to item I, characterized in that 2- (5-chloroquinolin-8-yloxy) acetic acid methyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2 - (5-chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid - (1-ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-pentylallyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid 5-chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5-chloroquinoline-8- yloxy) -acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -is gamma- (1-methyl-2-phenylethyl) -ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylpropyl) -ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester or 2- (5-chloroquinolin-8-yloxy) -acetic acid - [1-methyl-2- (4-methylphenoxy) ethyl] ester or an agent containing one of these compounds. 6. The method according to item 1, characterized in that 2- (5-chloroquinolin-8-yloxy) -acetic acid, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester or 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester or an agent containing one of these compounds contains, used. 7. The method according to item 1, characterized in that 2- (5-chloroquinolin-8-yloxy) acetic acid (1-methylisopentyl) ester or an agent containing this compound is used. 8. The method according to item 1, characterized in that one uses 2- (5-chloroquinolin-8-yloxy) -acetic acid ethers or an agent containing this compound. 9. The method according to item 1, characterized in that 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester or an agent containing this compound is used. 10. A method according to item I, characterized by using 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester or an agent containing this compound. 11. A method according to item 1 for protecting crop plants against damaging effects of herbicides of the formula II, characterized in that Y represents the groups -OR ¹⁸ , -SR ¹⁸ or -O-N = CR ¹⁹ R ²⁰ , wherein R ^{18 is} hydrogen , C ₁ -C ₄ -alkyl, Cy-C ₄ alkenyl, C ₃ -C ₄ alkynyl or Ci-C ₄ alkoxycarbonyl or di-C ₁ -C ₄ alkylamino-substituted C ₁ -C ₄ -alkyl and R ¹⁹ and R ²⁰ independently of one another C ₁ -C ₄ -A ^ yI or R ¹⁹ and R ²⁰ together denote a C ₄ -C ₇ alkylene chain. 12. The method according to item 11, characterized in that Y is methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, Dimethylaminoäthoxy, Propargyloxy, 1-cyano-i-methyl-ethoxy, Methoxycarbonylmethylthio, 1-Äthoxycarbonyl-ethoxy, Butyloxycarbonyl, -ON = C (CH ₃ ) ₂ , -ON = C (CH ₃ ) C ₂ H ₅ or-ON = C (CH ₂ ) ₅ . 13. The method according to item 1, characterized in that crops are protected against damaging effects of 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionate. 14. Method according to item 1, characterized in that crop plants protect against damaging effects of 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid propargyl ester. 15. The method according to item 1, characterized in that crops are protected against damaging effects of 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -thiopropionsäure-S-methoxycarbonylmethylester. 16. The method according to item 1, characterized in that crops are protected against damaging effects of 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) phenoxy] propionic acid (1-ethoxycarbonylethyl) ester. 17. Method according to item 1 for protecting crop plants against damaging effects of 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid methyl ester, 2- [4- (5-chloro-3- fluoropyridin-2-yloxy) -phenoxy] -propionic acid propargyl ester, 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -thiopropionic acid S-methoxycarbonylmethyl ester or 2- [4- (5-chloro-3- fluoropyridine ^ -yloxyJ-phenoxyJ-propionic acid-ii-ethoxycarbonyläthyO esters, characterized in that the crops, parts of these plants or for the cultivation of crops certain soils Isopropyl 2-quinoline-8-yloxyacetate, n-dodecyl 2- (5-chloroquinoline-8-yloxy) -acetic acid, n-butyl 2- (5-chloroquinoline-8-yloxy) -acetate, 2- (5 -Chloroquinolin-8-yloxy) -acetic acid-n-octyl ester, 2-quinolin-8-yloxy-acetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-octyl ester, 2- (5 -Chloroquinoline-8-yloxy) -acetic acid (2-butenyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid, methallyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-isopropyloxyethyl) ) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-Chloroquinoline-8-yloxy) -acetic acid cyclohexyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-methylpentyl) - esters, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid n-butyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3,6-dioxadecyl) ester, 2- (5-chloroquinoline-8 -yloxy) -acetic acid (3-methoxybutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-undecyl ester, 2- (5-Chloroquinolin-8-yloxy) -acetic acid (2-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid s-butyl ester, 2- (5-chloroquinolin-8-yloxy ) -acetic acid (3,6-dioxaheptyl) ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid n-heptyl ester, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid n-dodecyl ester, 2- (5-Chloroquinolin-8-yloxy) -thioacetic acid n-decyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy ) -acetic acid (1-methylisobutyl.) ester, 2- (5-chloro-quinolin-8-yloxy) thioacetic acid tert. butyl ester, 2- (5-chloro Hinolin-8-yloxy) -acetic acid neopentyl ester, 2- (5-chloro-quinol-8-yloxy) -thioacetic acid n-propyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid ethyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) i-butyl thioacetate, n-decyl 2-quinoline-8-yloxythioacetic acid, i-pentyl 2- (5-chloroquinolin-8-yloxy) -acetic acid, 2- (5-chloroquinolin-8-yloxy) acetic acid (1-ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-hexyl ester 2- (5-chloroquinolin-8-yloxy) -acetic acid n-hexyl ester, S-lB-chloroquinoline-S-yloxy-1-thioacetic acid i-propyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid ( 1-pentylallyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1,1-dimethylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethyl-1-meth ylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-butyloxycarbonylmethyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-n-butyloxycarbonylethyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid 5-chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid [1-methyl-2- (2-methylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid 5-chloroquinolin-8-yloxy) acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-) phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -6-acetic acid [1-methyl-2- (2-isopropyl-phenoxy) -ethyl] -ester, 2- (5-chloroquinolin-8-yloxy) acetic acid (1-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-ethylphenoxy) ethyl] ester, 2- (5- Chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (3-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid-e- (1-methyl-2-) phenoxyethyl) -este r, 2- (5-Chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2-one 3-methylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) acetic acid [1-methyl-2- (4-isopropylphenoxy) ethyl] ester, or 2- (5-chloroquinoline-8- yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester or an agent containing one of these compounds. 18. Method according to item 17, characterized in that the crops, parts of these plants or soils cultivated for the cultivation of the crops are treated with 2- (5-chloroquinolin-8-yloxy) -acetic acid ethers, 2- (5-chloroquinoline-8-yl) yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid ( 1-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloro-quinol-8-yloxy) -acetic acid (1-methylhexy!) Ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-ethylpentyl) -ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid Chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid (1-pentylallyl) ester, -v. 2- (5-Chloroquinolin-8-O) - (6-chloroquinoline-S-yloxy-acetic acid-2-methylpentyo-ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-methylisohexyl) -ester yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [ 1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- (5-chloroquinoline) 8-yloxy) -acetic acid (1-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid {1-methyl · 2-phenoxyethyl) ester, 2- {5-chloroquinoline-8- yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester or 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester or an agent , which contains one of these compounds treated. 19. The method according to item 17, characterized in that the crops, parts of these plants or for the cultivation of crops certain soils with 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2 (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester or 2- (5-chloroquinoline) 8-yloxy) -acetic acid methallyl ester or an agent containing one of these compounds. 20. The method according to item 1, characterized in that grain is protected. 21. The method according to item 20, characterized in that wheat, barley, rye and rice are protected. 22. The method according to item 1, characterized in that cultivated crop stands or cultivated areas for crops with 0.01 to 10 kg / ha of a compound of formula I after item. 23. The method according to item 22, characterized in that cultivated crop stands or cultivated areas for crops with 0.05 to 0.5 kg / ha of a compound of formula I according to item 1. 24. The method according to item 1, characterized in that treating seeds of crops with a compound of formula I according to item 1. 25. The method according to item 24, characterized in that treating seeds of the crop with 0.01 to 10g / kg seeds of a compound of formula I according to item 1. 26. The method according to item 25, characterized in that treating seeds of crops with 0.05 to 2g / kg seeds of a compound of formula I according to item 1. 27 · Method 24 of Protecting Crops Against Harmful Effects of 2- [4- (5-Chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic Acid Methyl Ester, 2- [4- (5-Chloro-3-) fluoropyridin-2-yloxy) -phenoxy] -propionic acid propargyl ester, 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] thiopropionic acid S-methoxycarbortylmethyl ester or 2- [4- (5-chloro 3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid (1-ethoxycarbonylethyl) ester, characterized in that the seeds of the crop plants with
2-quinolin-8-yloxy-acetate,
2- (5-chloroquinolin-8-yloxy) -acetic acid n-dodecyl ester,
2- (5-chloroquinolin-8-yloxy) -acetic acid n-butyl ester,
2- (5-chloroquinolin-8-yloxy) -acetic acid ^ n-oktylester, 2-Quinolin-8-yloxy-acetic acid> -butyl ester, 2- (5-chloro-orchinolin-8-yloxy) thioacetic acid n-octyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-butenyl) ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid methallyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-isopropyloxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) - ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid cyclohexyl ester,. 2- (5-chloroquinolin-8-yloxy) -acetic acid s-butyl ester, ". 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-methylpentyl) ester, n- butyl (6-chloroquinoline-S-yloxy-1-thioacetic acid, 2- (5-chloroquinolin-8-yloxy) -acetic acid (3,6-dioxadecyl) ester, 2- (5-Chloroquinolin-8-yloxy) -acetic acid (3-methoxybutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid (2-ethylbutyl) ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) - n-undecyl acetate, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (2-methyl-butyl) -ferential, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid-s-butyl ester, ^ - (B -Chloroquinoline-S-yloxyl-acetic acid O-dioxaheptyo-O, - - (δ-chloroquinolin-S-yloxy-acetic acid-n-heptyl ester, '2- (5-chloroquinolin-8-yloxy) -thioacetic acid-n- dodecyl ester, 2- (5-chloroquinoline-8-yloxy) -thioacetic acid-n-decyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylpropargyl) ester, ^ - (B-chloroquinoline-S tert-butyl 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid, N- (S-chloroquinoline-S-yloxy-acetic acid, 2- (5-chloroquinoline) -oxycarboxylic acid, N-methyl-isobutyl-O, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid; 8-yloxy) thioacetic acid n-propyl ester, 2- (5-chloroquinoline-8- yloxy) -egetic acid (1-methylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid ethyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid i-butyl ester,. 2-Quinolin-8-yloxy-thioacetic acid n-decyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid i-pentyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1 ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-hexyl ester, 2- (5 -Chloroquinolin-8-yloxy) -acetic acid n-hexyl ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid i-propyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-pentylallyl ) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1,1-dimethylpropargyl) ester, 2- (5-Chloroquinolin-8-yloxy) -acetic acid (1-ethyl-1-methylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid-n-butyloxycarbonylmethyl-ester, 2- (5 Chloroquinol-8-yloxy) -acetic acid (1-n-butyloxycarbonylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinoline-8 -yloxy) -acetic acid (1-pentylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-m Ethyl 2- (2-methylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5-chloro-orchinolin-8-yloxy) acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid 5-Chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-isopropylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1- ^i- phenylpropyl) ester , 2- (5-Chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) acetic acid [1- methyl-2- (3-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -insäure- (1-methyl-2-phenoxyethyl) ester, 2- (5-chloroquinoline 8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (3-methylphenoxy) ethyl] ester , 2- (5-Chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-isopropylphenoxy) ethyl] ester or 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl 2- (4-methylphenoxy) ethyl] ester or an agent containing one of these compounds treated. 28. The method according to item 27, characterized in that the seeds of the crop plants with 2- (5-chloroquinoline-8-yloxy) -acetic acid, the. , 2- (5-Chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, ^ - (B-chloroquinoline -e-yloxy-1-acetic acid-2-ethylbutyo-O, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid ( 1-methylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester . 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-pentylallyl) ester or 2- (5-chloroquinol-8-yloxy) -acetic acid (1-methylpentyl) ester or 2- (5-chloroquinoline) 8-yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid - (1-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-äthylphenoxy) -ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester or 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] -esteroder an agent containing one of these compounds treated. 29. The method according to item 27, characterized in that the seeds of the crops with 2- (5-chloroquinolin-8-yloxy) acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) (2-phenoxyethyl) -acetate, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, or 2- (5-chloroquinolin-8-yloxy) -acetic acid methallyl ester or an agent; which contains one of these compounds treated. 30. The method according to item 27, characterized in that grain is protected. 31. Use of compounds of the formula I according to item 1, characterized in that they are used for protecting crops against harmful effects of compounds of formula II according to item 1. 32. A method for the selective control of weeds in crop stands, characterized in that the cultivated plant stands, parts of the crops or cultivated areas of crops treated with an antidote of the formula I according to item 1 and a herbicide of the formula II according to item 1. 33. A herbicidal composition, characterized in that it contains in addition to a herbicidal active ingredient of the formula II according to item 1 an antidote of the formula I according to item 1. 34. Means according to item 33, characterized in that it contains, in addition to a herbicide from the series 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid methyl ester, 2- [4- (5- Chloro-3-fluoropyridin-2-yloxy) -phenoxy] -propionic acid propargyl ester, 2- [4- (5-chloro-3-fluoropyridin-2-yloxy) -phenoxy] -thiopropionic acid S-methoxycarbonylmethyl ester or 2- [4- (5 -Chloro-3-fluoropyridin-2-yloxy-phenoxy] -propionic acid (1-ethoxycarbonylethyl) -ester an antidote from the series 2-quinolin-8-yloxy-acetic acid isopropyl ester,
2- (5-chloroquinolin-8-yloxy) -acetic acid n-dodecyl ester,
2- (5-chloroquinolin-8-yloxy) -acetic acid n-butyl ester,
2- (5-chloroquinolin-8-yloxy) -acetic acid-n-oktylester,
2-quinolin-8-yloxy-acetic acid-s-butyl ester,
2- (5-chloroquinolin-8-yloxy) -thioessigsäure-n-oktylester,
2- (5-chloroquinolin-8-yloxy) -acetic acid (2-butenyl) ester,
2- (5-chloroquinoline-8-yloxy) -essigsäuremethal! Yl ester,
2- (5-Chloroquinolin-8-yloxy) -acetic acid (2-isopropyloxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid cyclohexyl ester,
2- (5-chloroquinolin-8-yloxy) -acetic acid-s-butyl ester,
2- (5-chloro-quino- ₁ ; n-8-yloxy) -acetic acid (2-methylpentyl) ester, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid n-butyl ester,
2- (5-Chloroquinolin-8-yloxy) -acetic acid (3,6-dioxadecyl) ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (3-methoxy-butyl) -ester, 2- (5 -Chloroquinoline-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylbutyl) ester, 2- (5-chloroquinolin-8-yloxy ) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-undecyl ester,
2- (5-chloroquinolin-8-yloxy) -acetic acid (2-methylbutyl) ester, 2- {5-chloro-quinolin-8-yloxy) -thioacetic acid s-butyl ester,
2- (5-chloroquinolin-8-yloxy) -acetic acid (3,6-dioxaheptyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid n-heptyl ester,
2- (5-chloroquinolin-8-yloxy) -thioessigsäure-n-dodecyl ester, 2- (5-Chloroquinolin-8-yloxy) -thioacetic acid n-decyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy ) -acetic acid (1-methylisobutyl) ester, 2- (5-chloro-quinolin-8-yloxy) -thioacetic acid-tert-butyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid neopentyl ester, 2- (5 -Chloroquinolin-8-yloxy) -thioacetic acid n-propyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) thioacetic acid ethyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-ethylhexyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid i-butyl ester, 2-quinolin-8-yloxy-thioacetic acid n-decyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid i-pentyl ester, 2- (5-chloro-quinolin-8-yloxy) -acetic acid (1-ethylpentyl) ester, 2- (5- Chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -thioacetic acid n-hexyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid-n hexyl, 2- (5-chloroquinolin-8-yloxy) thioacetic acid i-pr Optyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-pentylallyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid 5-Chloroquinolin-8-yloxy) -acetic acid (1,1-dimethylpropargyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethyl-1-methylpropargyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid 5-chloroquinolin-8-yloxy) -acetic acid n-butyloxycarbonylmethyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-n-butyloxycarbonylethyl) ester, 2- (5-chloroquinoline-8-yl) yloxy) -acetic acid (1-methylisohexyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [ 1-methyl-2- (2-methylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid 5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-isopropylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid - (1-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (2-ethylphenoxy) ethyl] ester, 2- (5-chloroquinoline-8- yloxy) -acetic acid- [1-methyl-2- (3-ethylphenoxy) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2 - (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (3-methylphenoxy ) ethyl] ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-isopropylphenoxy) ethyl] ester or 2- (5-chloroquinolin-8-yloxy) - acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester. 35. Means according to item 34, characterized in that it contains an antidote from the series of 2- (5-chloroquinolin-8-yloxy) acetic acid methallyl esters, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-ethylbutyl) ester, 2- (5-chloroquinoline-8-yloxy) -acetic acid 5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester, 2- (5-chloroquinoline-8- yloxy) acetic acid (1-ethylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-propylbutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid ( i-pentylallyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylpentyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisohexyl) ester , 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylisobutyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylethyl) ester, 2- (5- Chloroquinolin-8-yloxy) -acetic acid [1-methyl-2- (4-ethylphenoxy) ethyl] ester, 2- (5 -Chloroquinolin-8-yloxy) -acetic acid (1-methyl-2-phenylethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-phenylpropyl) ester, 2- (5-chloroquinoline -8-yloxy) -acetic acid (1-methyl-2-phenoxyethyl) ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methyl-3-phenylpropyl) ester, or 2- (5 Chloroquinol-8-yloxy) -acetic acid [1-methyl-2- (4-methylphenoxy) ethyl] ester. 36. Means according to item 34, characterized in that it contains as antidote 2- (5-chloroquinolin-8-yloxy) -acetic acid, methallyl ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (2-phenoxyethyl) -ester, 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylisopentyl) ester or 2- (5-chloroquinolin-8-yloxy) -acetic acid (1-methylhexyl) ester.