DD201965A5 - HERBICIDE MEDIUM - Google Patents

Abstract

The invention relates to herbicidal compositions containing a solid or liquid Traegerstoff and a cyclohexane derivative of the general formula in which R is high alkyl with 1 to 4 carbon atoms, R is highly alkyl 2 with 1 to 4 carbon atoms, alkenyl having 3 to 4 carbon atoms, alkynyl with 3 to 4 carbon atoms or haloalkenyl having 3 or 4 carbon atoms u. 1 to 3 halogen atoms, X is straight or branched alkylene radical having 1 to 5 carbon atoms, optionally phenyl-substituted, n = 0 or 1, Y is a nonaromatic heterocycle having 4 to 7 atoms and no or one double bond in the heterocyclic ring, containing 1 or 2 heteroatoms from the Group sulfur, nitrogen, oxygen in any order, wherein the heterocycle is optionally substituted by alkyl, Z is hydrogen o. Methoxycarbonyl and the salts of this compound.

Description

Characteristics of the known technical solutions Cyclohexandionderivate with thienyl or Furylsubstitution in the 5-position with relatively low herbicidal activity are known (DE-AS 24 39 104).

Object of the invention

The aim of the invention is the development of herbicidal agents with improved efficiency in weeds, but crops are not damaged.

Explanation of the essence of the invention

The invention has for its object to provide new chemical compounds with herbicidal activity.

It has now been found that compounds of the general

Formula I.

30 in the

R ¹ alkyl with 1 to 4 carbon atoms "

R ^{2 is} alkyl of 1-4 carbon atoms, alkenyl of 3 to - ^: . '4 carbon atoms, alkynyl of 3 to 4 carbon atoms or haloalkenyl of 3 or 4 carbon atoms

35 atoms and 1-3 halogen atoms

240232 4

0050/35177

X is straight-chain or branched alkylene radical having 1 to 5 carbon atoms, optionally phenyl-substituted η = 0 or 1 Y is a nonaromatic heterocycle having 4 -

7 atoms and no or one double bond in the heterocyclic ring, containing 1 or 2 heteroatoms from the group sulfur, nitrogen, oxygen in any order, wherein the hetero-K3. cyclus is optionally substituted by alkyl Z is hydrogen or methoxycarbonyl and the salts of these compounds fight unwanted plants from the family of grasses very well and at the same time possess as selective herbicides a high degree of compatibility for broadleaf and other non-family of grasses counting crops.

R is, for example, Propy.1, ethyl, butyl, R is, for example, methyl, ethyl, propyl, allyl, 2-chloroallyl, 3-chloroallyl,

X is, for example, methylene, ethylene, Y is, for example, tetrahydropyranyl, dihydropyranyl, methyltetrahydropyranyl, dioxanyl, dioxolanyl, dithiolanyl,

Dihydrothiopyranyl.

The novel compounds can exist in various tautomeric forms:

OR

The present invention includes all of these forms.

2402 3 2 U -3-

0050/35177

* "For the preparation of the new compounds, for example, the following way is suitable:

a)

+ R ₂ ONH,

Where R, R, X, Y, Z, A have the abovementioned meaning

The reaction is advantageously carried out in heterogeneous phase in an inert solvent at temperatures between 0 and 80 ⁰ C in the presence of a base.

Examples of bases are carbonates, bicarbonates, acetates, alcoholates, hydroxides or oxides of alkali or alkaline earth metals, especially of sodium and potassium, and also magnesium and potassium. In addition, can also

2Q. organic bases such as pyridine or tertiary amines find use.

A defined pH range which is particularly suitable for the reaction ranges from pH 2 to pH 7, in particular from pH 4.5 to pH 5.5. The adjustment of the pH range for the reaction is advantageously carried out by addition of acetates, for example Alkallacetaten, in particular sodium or potassium acetate or their mixtures. The alkali metal acetates are used, for example, in amounts of 0.5 to 2 mol, based on the ammonium compound.

Suitable solvents are, for example, methanol, ethanol, isopropanol, benzene, tetrahydrofuran, chloroform, acetonitrile, dichloroethane, ethyl acetate, dioxane, dimethyl sulfoxide.

240232 h - »-

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The reaction is complete after a few hours, the reaction product can be isolated by concentration of the mixture, addition of water and extraction with a non-polar solvent and distilling off the solvent under reduced pressure.

b) In addition, the preparation of the new compounds by reacting the compounds II with the corresponding amines R ^ -ONH ₂ feasible.

c) Furthermore, the preparation of the new derivatives is also possible by alkylation of the oximes with alkylating agents:

, 0H 15

Il

¹ + R ² -X 'base

OH χ Γ OH

20 ^y

The process a) is preferred.

The compounds of formula II can be obtained by acylation of the cyclohexane-1,3-diones III as described in Tetrahedron Letters 29, 2491. The compounds III can also be present in tautomeric forms.

• 0. 0 OH

III III a III b

Compounds of the formula III are known from aldehydes Y-X-CH = O nach.literaturbekannten methods exemplified

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by aldol condensation with ketone and subsequent cyclization with malonic acid ester, analogous Organic Synthesis Coll. Vol. II, page 200 can be produced. Also by reaction of the aldehyde YX-CH = O with malonic acid according to Knoevenagel-Döbner (see Org., Reaction Vol. 15 , page 204), esterification of the resulting acid and cyclization with acetoacetic ester, in an analogous manner as described, for example, in Chem. JhS, page 2946, one arrives at the intermediates of formula III.

The salts of the compounds are, for example, the alkali metal salts, in particular sodium or potassium salts.

The sodium and potassium salts of the novel compounds can be obtained by treating these compounds with sodium or potassium hydroxide in aqueous solution or in an organic solvent such as methanol, ethanol, acetone. It is also possible to use alkali metal alkoxides as bases.

Other metal salts, e.g. the manganese, copper, zinc, iron or barium salts can be prepared from the sodium salt by reaction with the appropriate metal chloride in aqueous solution. The following examples illustrate the preparation of the new cyclohexanedlones (parts by weight are in terms of parts by volume, such as kilograms to liters).

example 1

10.0 parts by weight of 2-butyryl-4-methoxycarbonyl-5 [-tetrahydropyran-4-ylmethyl] -cyclohexan-l, 3-dione were dissolved in 150 parts by volume of ethanol and 2.93 parts by weight Ethyloxiammoniumchlorid and 2.71 parts by weight of anhydrous sodium acetate , After stirring for 20 hours

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2O ⁰ C was added to ice water and extracted with methylene chloride. After concentration of the organic phase remained 10.5 parts by weight of 2 (1-ethoxyaminobutylidene) -4-methoxycarbonyl-5- [tetrahydropyran-4-ylmethyl] cyclohexane-l, 3-dione (compound no. L) as a viscous oil with the following Structure:

Ber C 63.0 H 8.2 N 3.7 Gef C 63.3 H 8.1 N 3.7

Example 2

10.0 parts by weight of 2-butyryl-5 [2- (1,3-dioxan-2-yl) -ethyl] -cyclohexane-1-dione were dissolved in 150 volumes of ethanol and 3.72 parts by weight of allyloxiammonium chloride. and 3.03 parts by weight of anhydrous sodium acetate and stirred at 20 ⁰ C for 20 hours. The suspension was then stirred into ice-water and extracted with methylene chloride. After concentration of the organic phase remained 11.5 parts by weight of 2- (1-allyloxiaminobutylidene) -5- [2- (l, 3-dioxan-2-yl) ethyl] -cyclohexan-l, 3-dione (Compound No. 2 ) as a pesticide having the following structure (melting point 50 to 52 ⁰ C):

240232 U

° ' ^z - 0050/35177

/ OCH ₂ CH = CH ₂ NH

C ₁₉ H ₂₉ O ₅ N 64 M = 351 8th, 3 N 4 , 0 Ber: C 65 , 9 H 8th, 1 N 3 , 7 Gef: C ,1 H Example 3

12.0 parts by weight of 2-butyryl-4-methoxycarbonyl-5- [2- (l, 3-di-thiolan-2-yl) ethyl] -cyclohexan-l, 3-dione were dissolved in 150 parts by volume of ethanol and washed with 3 , 29 parts by weight. AHyloxiammoniümchlorid and 3.28 g of anhydrous sodium acetate. After 20 hours of stirring at 20 ⁰ C was added to ice water and extracted with methylene chloride. After concentration of the organic phase remained 13.1 parts by weight of 2- (1-allyloxiaminobutylidene) -4-methoxycarbonyl-5- [2- (l, 3-dlthiolan-2-yl) ethyl] cyclohexane-l, 3- dion (Compound No. 3) as a viscous oil having the following structure:

O NH

2Λ0232 4 - 8 - ° · ² · 0050/35177

" ^C 2O ^H 29 ° 5 ^NS 2 ^{M =}

Calcd: C 56.2 H 6.8 N 2.3 · S 15.0 Gef: C 57.0 H 6.7 N 2.8 S 14.7

The following compounds were obtained in a similar manner:

V.

Ut

ro

^r Verblndung R ¹ R ² X -Y η Il Il Z > CbOCH CÖOCH No. ι1 Il (2-H) -5,6-dehydropyran-3-yl CÖOCH H CbOCH J " propyl allyl Te rahyd ropyran-4-ylmethyl l-phenyl-2- (1,3-dloxolan- It H CbOCH., CbOCH 3 5 Il ethyl Il 2-yl) ethyl Il H 3 H 6 Il allyl ti COOCH • 7 Il allyl 2- (1,3-dioxan-2-yl) -ethyl H 8th 11 ethyl It CÖOCH 9 It allyl 1 | -Methyl tartrate ropy r an-3-yl H 10 It ethyl Il H 11 Il allyl It GbOGIL · 12 Il ethyl l- (l | methyl-l, 3-dloxan-2-yl ~) 5 2-methyl-propyl 13 Il allyl 14 Il ethyl 15 Il ethyl 16 Il allyl 17 Il ethyl 18 Il allyl 19 Il ethyl

Pp or refractive index

η ²² 1.5235

1.5297

n ²⁰ 1.5339

OJ

VO

O O

VJI

LO VJI

Ut Ul

^r concealment no.

20 21 22 23

25 26

27 28 31 32 36

propyl

Il '

K>

Ethyl allyl ethyl allyl ethyl allyl

Il ax xyx " Il 3-chloroallyl H 2-chloroallyl Il 3-chloroallyl Il 2-chloroallyl Il Il

X -Y η

(l | -H) -2,3-dihydropyran-2-yl COOCH

Tetrahydropyran-2-yl

Tetrahydropyran ^ l-ylmethyl

Il

Pp or refractive index

1.5225

lH) -2,3-Dlhydropyran - / - yl COOCH n ^ ⁷ 1.5262

COOCH ₃ n ^ 1.5142

COOCH ₃ njp 1.5204

1.5136

2- (l, 3-Dloxan-2-yl) ethyl

H n ^{27 n} D 1.5200 H n ²¹ * D 1.5149 cdocH J- * Pp 75-7 $ ° 72-75 C (JOCH pp H H 55-58 ° H "Pd

Ut Ol j *} ul S ui ο 4-methyltetrahydropyran-3-yl Z H ul 1 Pp or refractive index ΓΟ 1-phenyl-2- (1,3-dioxolan-2-yl) ethyl H | Ν Connection no. R ¹ R ² X -Y η (4-H) -2,5-dimethyl-2,3-dihydro-pyran-2-yl H S M H η ²² 1.5281 OO (2-H) -5,6-dihydrotlopyran-3-yl H η ²² 1.5401 ΓΟ 37 propyl 3-chloroallyl 2- (1,3-dioxan-2-yl) ethyl Il H η ²² 1.5389 38 Il 2,3,3-trichloroallyl » H 41 t if 3-chloroallyl (2-H) -2,6-dimethyl-5,6-dihydro-thiopyran-3-yl H rip ⁸ 1.5259 ι. 44 Il allyl Il nj ^b 1.5301 M I 48 ff ethyl vl 4-meth-vinyltetrahydro-dvran-3-vl H η ²³ 1.5620 49 Il allyl H η ²³ 1.5678 61 ti ethyl H 62 H allyl "ρ ³ 1,5464 P IM K η ²³ 1.5510 O / -Ν 65 Il ethyl 350/3 66 Il allyl Ul H * -4 68 , Il 2.3.3-Trichlorall

Ut

Ni

^r concealment no. R R 71 propyl propargyl 72 Il propyl 76 Il allyl 77 ethyl ethyl 78 Il allyl 79 propyl allyl 80 ethyl ethyl 81 ethyl allyl 83 It ethyl

X -Y η

4 ~ methyltetrahydropyran-3-yl H

(2-H) -5 _> 6-Dlhydropyran-3-yl

Te rahyd ropyran-2-yl

Tetrahydropyran-3-yl

(2 H) -2,6-dimethyl-5,6-dlhydrothiopyran-3-yl

AllylHHHHHHH

H H

Pp or refractive index

n ^ 1.5332 n £ ⁶ 1.5181 nj ⁸ 1.5449 η ³ / 1.5199 n ³¹ 1.5265 nj ⁸ 1.5313 pp 38-40 °

nj ⁸ 1.5312

η} " ³ 1.5549 n £ ³ 1.5608

ro co ro

O O Ul O

^r connection no.

ethyl

propyl

to

(Ji

X -Y η

ul

Ethyl allyl ethyl allyl ethyl

Allyl (2H) -5,6-dlhydrothipyran-3-yl H

Tetrahydrofuran-2-yl

(2 H) -2,6-Dlmethyl-5,6-dihydropyran-3-yl

H H H H

Sodium salt of compound no.

The following compounds can be obtained in a similar way:

Pp or refractive index

r £ ⁵ 1,5689 n £ ³ 1> 5727 njj ¹ 1,5179 n ^ ¹ 1,5261

1.5275

Pp 168-172 ^C (Zers.)

U) VJI

ro inUl

Connection no.

X -Y η

Propyl 2,3,3-trichloroallyl tetrahydropyran-4-ylmethyl

Il Il Il Il Il Il

2,3-Dibromallyl

3-chloroallyl

2-chloroallyl

2,3-dichloroallyl

2,3-Dibromallyl

3-chloroallyl

45 Il allyl 46 Il ethyl 47 Il 3-chloroallyl 50 Il H 51 Il ethyl 52 Il 3-chloroallyl

2- (1,3-dioxan-2-yl) ethyl

Il M

1- (4-methyl-1,3-dioxan-2-yl) -2-methyl-propyl

1-Phenyl-2- (1,3-dioxolan-2-yl) ethyl 2- (1,3-dithiolan-2-yl) -ethyl

(4-H) -2 _J 5-Dimethyl-2 _> 3-dihydropyran-2-yl 2,5-dimethyltetrahydropyran-2-yl

COOCH. COOCl · HCOOCH,

cöochJ

H H H

H H H H

H H

O O UI O

ul a In » in ^r connection R ¹ R ² No. 53 propyl 3-chloroallyl 54 · Il ethyl 55 Il allyl 56 Il 3-chloroallyl 57 Il It 58 Il Il 59 Il Il

oil

X -Y η

Ut

ethyl

(2-H) -5,6-Dihydropyran-3-yl (4-H) -2. 3-Dlhydropyran-2-yl

Tetrahydropyran-3-yl tetrahydropyran-2-yl

(2 H) -2,6-Dlmethyl-5,6-dihydrothlopyran-3-yl

(2 H) -5,6-dihydrothiopyran-3-yl

H H H H H H

COOCH,

63 Il 3-chloroallyl Il H s It allyl (2 H) -2,6-Dlmethyl-5,6-dl- COOCH hydridopyran-3-yl 67 Il 2-chloroallyl Jj-methyltetrahydropyran-3-yl H 69 ethyl ethyl Il H 70 η allyl Il H 73 propyl butyl It H 7 h ethyl ethyl (2 H) -5,6-Dlhydropyran-3-yl H 75 It allyl ti H

IN

ro ro

UI I

O O vLn O \ Ui VJI

ca Ul R ¹ ul connection R ² No. propyl 82 Il allyl 87 Il ethyl 88 ethyl allyl 89 Il ethyl 90 propyl allyl 93 Il ethyl 9 ¹ I ethyl allyl 95 It ethyl 96 propyl allyl 97 Il ethyl 98 ethyl allyl 101 It Il 102 propyl ethyl 103 Il Il ΙΟΊ ethyl allyl 105 Il ethyl 106 allyl

rJ O

Oi

X -Y η

ul

2,5-Dimethyltetrahydropyran-2-yl H tetrahydrothop-3-yl H

Il

Tetrahydrofuran-3-yl

H H H H

" H

¹¹ h

·· H

(6r-H) -H, 5-dlhydropyran-3-yl H

" H

(2-H) -2,6-Dimethyl-5,6-dihydropyran-3-yl

• I

2,6-Dime thyltet rahyd ropyran-3-yl H

¹¹ h

¹¹ h

¹¹ h

Ut

Ut R ¹ UH ui r connection propyl R ² Mn Il , - Vi 1 · __-.-- 107 ti ethyl 108 Il allyl 109 Il ethyl 110 allyl 111 3-chloroallyl

1 _J 3-dioxep-5-yl

Il

2- (1,3-dithian-2-yl) ethyl

Π3 calcium salt of compound no. 26

114 copper salt of compound no. 26

115 sodium salt of compound no. 79

116 sodium salt of compound no. 19

117 calcium salt of compound no. 19

Il

H H H H H

OJ

O O VJI O \ OJ

240232 · 4 _: . ₁₈ .

0050/35177

The 1 H NMR spectral data recorded on these compounds are listed in the following table. The chemical shifts were referenced to tetramethylsilane as internal standard and reported in <f-values (ppm). 5

The solvent used was CDCl ₃ J abbreviations for the signal structures

s singlet

10 d Düblet t

t triplet

q Quartet

m multiplet with more than four lines

IS Connection No. - Characteristic Signals'

HH 0 -CH ₂ - 4.06 (q) 5.75 (s) COOCH 1 4.09 (q) 4.51 (d) 3.75 (s) 2 4.51 (d) - 3 4.51 (d) 3.77 (s) 4 4.51 (d) 3.78 (s) 5 4,11 (q) - 6 4,52 (d) - 7 4.51 (d) 3.76 (S) 8th 4.08 (q) - 9 4.50 (d) 3.78 (S) 10 4.08 (q) - 11 4,58 (d) 12 4.09 (q) 3.74 (S) 13 4,54 (d) 3.78 (S) 14 15 3.69 (S) 16 3.70 (S) 17 3.78 (S)

240232 k

- 19 - ^υ · ^ώ - 0050/35177

* "Connection No.,. Characteristic signals

HH 0-CH ₂ COOCH-

18 5.75 Cs) 4.50 (d) 3.75 (s)

19 - 5.60 (s) 4.10 (q)

20 4.65 (m) 4.10 (q) 3.75 (s) ⁺⁾

6,20 (m)

21 4.70 (m) 4.60 (d) 3.70 (s)

6.30 (m)

22 - 4,11 (q) 3,75 (s)

3.80 (s)

23 - 4.52 (d). 3.75 (s)

3.80 (s)

24 - 4,12 (q) 25 -. 4.51 (d)

26 - 4.05 (q)

31 - 4.50 (m)

32 - 4.56 (s) 44 - 4.50 -

68 - 4.89 (s)

The splitting of the ester signals is caused by diasteromerism.

The application as herbicide takes place e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions * pastes, dusts, scattering agents, granules by spraying, brushing, impregnating, atomising, dusting, scattering or pouring. The application modes depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the new active ingredients.

For the production of directly sprayable solutions, emulsions, pastes and oil dispersions come mineral oil fractions

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of medium to high boiling point, such as kerosene or diesel oil, coal tar oils, etc., and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, for example methanol , Ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorane, etc., strongly polar solvents, eg Dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc. into consideration.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders), öldispersic- NEN be prepared by addition of water. For the preparation of emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.

The herbicides contain, for example, 5 to 95 % (wt .- *), in particular 10 to 80 % active ingredient.

Surfactants include:

Alkali, alkaline earth, ammonium salts of lignosulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylarylsulfonates, alkylsulfates, alkylsulfonates, alkali and alkaline earth salts of dibutylnaphthallanesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty alkali and alkaline earth salts, salts of sulfated hexadecanols, heptadecanols, octadecanols, salts of sulfated pettal alcohol glycol ethers, Condensation products of sulfonated! Naphthalene and naphtha

240232 4

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'"derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenolether, ethoxylated isooctylphenol, octylphenol, nonylphenol, Alkylphenolpolyglykoläther., Tributylphenylpolyglykolether, Alkylarylpolyätheralkoholate, Isotridecylalkohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, Polyoxyethylenalkylether, ethoxylated polyoxypropylene , Lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, liquor liquors and methylcellulose.

Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.

Granules, e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers. Solid carriers are e.g. Mineral earths such as silicas, silicates, talc, kaolin, lime, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flours, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.

embodiments Example a

90 parts by weight of compound 1 are mixed with 10 parts by weight of N-methyl-alpha-pyrrolidone, giving a solution which is suitable for use in the form of very small drops

 35

240232 H - 22 - ^α2 · ΟΟ5Ο / 35177

Example b

10 parts by weight of compound 2 are dissolved in a mixture of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of ricinium

Example c

20 parts by weight of compound 3 are dissolved in a mixture consisting of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.

20 Example d

20 parts by weight of compound 1 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 28O ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil.

Example e

80 parts by weight of the active compound 1 are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a SuIfit waste liquor and 7 parts by weight of powdered silica gel

35 mowing a hammer mill. '

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Example f

5 parts by weight of compound 1 are intimately mixed with 95 parts by weight of finely divided kaolin. Obtained in this way a dust containing 5 percent by weight of the active ingredient.

Example g

30% by weight of compound 1 is intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. Obtained in this way a treatment of the drug with

15 good adhesion.

Example h

.40 parts by weight of the active compound 1 are intimately mixed with 10 parts • 20 sodium salt of phenol sulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained.

25 Example i

20 parts of the active compound 1 are intimately mixed with 12 parts of calcium dodecylbenzenesulfonate, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. This gives a stable oily dispersion.

0232 4. - 24 - 0-2. 0050/35177

^p The effect of the new cyclohexane-l, 3-dione derivatives on the growth of plants from the grass family (Gramineae) and broadleaf crops can be demonstrated by greenhouse and field trials. Crops from the Gramineae family can also die off or be severely damaged. This may well be desirable in practice, as crops may also become undesirable plants when grown from the soil in another crop, such as volunteer barley in winter rape or soybean in soybean fields.

The culture vessels used for the experiments were plastic flower pots with a content of 300 cm and loamy sand with about 1.5 % IS humus as substrate. For soya, some peat was added to ensure better growth. The seeds of the test plants were sown flat separately by species.

20 'In the pre-emergence treatment, the active ingredients were applied to the surface of the earth. They were suspended or emulsified in water as a distribution medium and sprayed by means of finely distributing nozzles. In this application method, the application rate was 3.0 kg of active ingredient / ha. After application of the agents, the vessels were lightly rained to induce germination and growth. Thereafter, the containers were covered with transparent plastic hoods until the plants had grown. The cover caused a uniform germination of the test plants, if so

30 was not affected by the active substances.

For the postemergence treatment, the plants were grown, depending on the growth habit, to a stature height of 3 to 15 cm

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The application rates for the post-emergence treatment varied depending on the active ingredient and the application target, amounting to 0.125, 0.25, 0.5 and 1.0 kg of active ingredient / ha.

As a comparative example (DE-AS 24 39 104) served each post-emergence '

with 0.25 kg / ha as well

and

/ N-OCH ₃ CH = CH

^C 3 ^H 7n (DE-AS 2 439 104)

• A

^C 3 ^H 7n

with 0.25 and 0.5 kg / ha each.

In carrying out the greenhouse experiments, heat-loving species in warmer areas (20 to 35 C) and temperate climates were preferred at 10 to 20 ^° C. The experimental period was 2 to 4 weeks. During this time, the plants were cared for, and their response to each treatment was evaluated.

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The rating is based on a scale from 0 to 100. 0 means no damage or normal rising and 100 no rising or complete destruction of at least the above-ground sprite parts.

In the supplementary field experiments, the agents on small plots were also emulsified in water as a distribution medium or suspended postemergence. One used for this purpose a mounted on a tractor parcel sprayer. The application rates were 0.25 kg / ha. The control target was volunteer barley in young winter rape.

The following test plants were used for the presentation of the results:

Botanical name

German name

English name

Alopecurus myosuroides Avena fatua

Avena sativa

Beta vulgaris

Brassica napus Bromus tectorum Echinochloa crus-galli

Gossypium hirsutum

Glycine max.

Hordeum vulgar Lolium multiflorum Rottboellia exaltata

Setaria spp.

Sorghum bicolor

Sorghum halepense Triticum aestivum Zea mays

Foxtail

oats

oats

sugar beets

rape

Downy brome

barnyardgrass

cotton

soybeans

barley

Ital. ryegrass

Foxtail species

sorghum

Sudan grass

wheat

Corn

black grass

wild oats

oats

suggarbeets.

rape seed

downy brome

barnyard grass s

cotton

soybeans

barley

annual ryegrass

itchgrass

foxtail

sorghum

Johnson Grass

wheat

indian corn

240 23 2 4

- · 27 - ° · ² - 0050/35177

The results show that the new compounds are useful in post-emergence application for control of unwanted plants from the grass family (Gramineae), which may be typical grass weeds such as Plughafer (Avena fatua) or crops the gramineous family, which become undesired plants in the wrong location (eg maize in a soybean field) Individual compounds, "combating" of one millennium, on the other hand, exhibit, besides their good selectivity for broadleaf crops, a high degree of tolerability for wheat , which in turn belongs to the grass family.

Examination of the herbicidal action with postemergent application of 0.25 kg / ha of Compound No. 26 gave an average control value of 81 against nine species of grass. Using the same application rate and method, compound No. 24 reached a value of 74.

..

On the other hand, the known comparison agent A also had an average effect of 52 % on postemergence application of 0.25 kg of active ingredient / ha against the same grass species . The two further comparison agents B and C showed a comparatively weak herbicidal activity.

Broad-leaved crops such as cotton (Gossypium hirsutum), soybean (Glycine max.), Sugarbeet (Beta vulgaris) and oilseed rape (Brassica napus) remained completely harmless in these treatments or showed only negligible impairment of growth. This results in a high degree of selectivity for dicotyledonous cultures for the new compounds. In addition, some of the new compounds, such as e.g. the number 31 and

240232 4

- 28 - O.Z .. 0050/35177

0.25 kg of active ingredient per hectare of unwanted grasses, such as field foxtail and millet, and at the same time behaved selectively for the useful grass wheat.

With regard to herbicidal activity, in a number of other examples, the effect of the new compounds on plant species from the grass family could be demonstrated, e.g. Nos. 2, 10, 11, 19, 24 and 26.

φ In the described greenhouse experiments, the compounds Nos. 1, 4, 5, 8, 31, 32, 36 and 37 also provided a comparatively good control effect in postemergence application.

In field trials, postemergent application of 0.25 kg of active ingredient / ha of compounds Nos. 10, 11 and 26 was selectively combated in rapeseed.

In addition to the post-emergence effects, positive results were also obtained with pre-emergence application of the new compounds in the greenhouse. Thus at 3.0 kg of active ingredient / ha in this method of application Compounds Nos. 2, 5, 8, 10, 14, 19, 26, 32, 36, 37, 48, 49, 54, 55, 77 and 78 worked strongly herbicide against the grassy example plants oats, ryegrass and millet. Likewise, compounds No. 1, 3 and 4 had a considerable herbicidal activity against these grass types just mentioned in the greenhouse at 3.0 kg / ha in the pre-emergence application.

In view of the good compatibility, the novel herbicides or agents containing them may be used in a further large number of crop plants to eliminate undesired plant growth. The application rates can be between 0.1 and 15 kg / ha and

35 more sway.

U)

Nt O

ul

^r example, are the following crops Considering. Botanical name 'German name English name

Allium cepa

Pineapple comosus

Arachis hypogaea

Asparagus officinalis

Beta vulgaris spp. altlssima Beta vulgaris spp. rapa

Beta vulgaris spp. esculenta Brassica napus var. napus Brassica napus var. napobrasslca Brassica napus var. rapa

Brassica rapa var. Sllvestrls Camellia sinensis

Carthamus tinctorius

Carya illinoinensis

Citrus limon

Citrus maxima

Citrus reticulata

Citrus sinensis

Coffea arablca (Coffea canephora, Coffea liberlca)

Cucumis rnelo

onion

pineapple

Peanut

asparagus

sugar beet

mangel

Red beet

rape

Turnip

White turnip

rape

Teestrauch

Safflower - safflower

Pecan

lemon

grapefruit

tangerine

Orange, orange

coffee

Melon onions

pineapple

peanuts

asparagus

sugarbeets

fooder beets

table beets, red beets

rape seed

turnips

tea plants safflower pecan trees lemon grapefruit

orange trees coffee plants

melons

U) VJl

Botanical name

Cucumis sativus Cynodon dactylon

Daucus carota Elaeis guineensis Pragaria vesca Glyoine max

Gossypium hirsutum (Gossypium arboreum Goasyplum herbaceum Gossypium vltlfollum) Helianthus annuus Hellanthus tuberosus Hevea braslliensis Humulus lupulus Ipomoea batatas Juglans regia Lac-tua sativa Lens culinaris Linum usltatissimum Lycopersicon lycopersicum Malus spp.

German name

ut

ul

Cucumber bermuda grass

Carrot oil palm strawberry soybean

cotton

sunflower

Jerusalem artichokes

Para rubber tree

hop

sweet potatoes

walnut tree

lettuce

lens

flax

tomato

Apple

English! · Name

cucumber

Bermuda grass in turfs and lawns

carrots oil palms strawberries soybeans

cotton

sunflowerfe

rubber plants

sweet potato

walnut trees

lettuce

lentils

flax

tomato

apple trefes

O UI O

Ud VJl

ul

ul

^r Botanical name

German name

English name

Manihot esculenta Medicago sativa Metha piperita Musa spp.

Nlcotiana tabacum (N. rustlca) Olea europaea Phaseolus lunatus Phaseolus mungo Phaseolus vulgaris

Pennisetum glaucum

Petroselinum crispum spp. tuberosum Picea abies Abies alba Plnus spp. Pisum sativum Prunus avium Prunus domestica

manioc

alfalfa

peppermint

Fruit and flour banana

tobacco

Olive tree lunar bean

Perl or cattail millet

root parsley

Rotfichte

white fir

pine

garden pea

sweet cherry

plum

cassava

alfalfa (lucerne)

peppermint

banana plants

tabacco

olive trees

lima beans

mung beans

snapbeans, green beans, dry beans

parsley

Norway spruce

pine treefe

English pfeas

cherry trètes

plum treefe

O O VJI O

tv *

Botanical name

German name

English name

Prunus dulcis Prunus persica Pyrus communis Ribes sylvestre Ribes uva-crispa Rlclnus communis Saccharum officinarum Sasamum indicum Solanum tuberosum Sorghum bicolor (see vulgar)

Spinacia oleracea Theobroma cacao Trifolium pratense Triticum aestivurn Vaccinium corymbosum Vacclniurn vitis-idaea Vicia faba Vigna sinensis (V. unguiculata) Vltis vlnlfera Zea mays *

almond

peach

pear

Red currant

gooseberry

castor-oil plant

sugarcane

sesame

potato

sorghum

(In foliar application)

(Post-directed)

Spinach cocoa tree; Red clover wheat

Cultivated Blueberry Cranberry Horse beans. Cow bean Grapevine

Corn

(Bottom sheet spraying) (post-directed)

almond tribes peach tretes pear treefe red currahts

sugar cane

Sesame

Irish potatoes

sorghum

spinach cacao plants red clover wheat blueberries cranberry tick beans cow peas grapes

Indian corn, sweet corn maize

O O Ul O

23

-33- ^αΖ - 0050/35177

To widen the spectrum of action and to achieve synergistic effects, the new cyclohexane-1,3-dione derivatives can be mixed with known cyclohexane-l ^ -dione derivatives and with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together. For example, diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazlnones, 2,6-dinitroanilines, N-phenylcarbamates,

Satires, Trtaz

Ureas, "diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-ljS-dione derivatives and others." "Useful mixtures give the compounds according to the invention, depending on the intended use, with the following active substances:

240232 ** -34- ° · ^ζ · 0050 / 351-77

5-Amino-4-chloro-2-phenyl-3 (2H) -pyridazinone 5-Amino-4-bromo-2-phenyl-3 (2H) -pyridazinone 5-amino-4-chloro-2-cyclohexyl 3 (2H) -pyridazinone

5-Amino-4-bromo-2-cyclohexyl-3 (2H) -pyridazinone 5

5-Metfaylamino-4-chloΓ-2- (3-trifluoromethylphenyl) -3 (2H) -

-pyridazinone

5-methylamino-4-chloro-2- (3-alpha-alpha-beta-beta-tetra-

3-chloro-4-chloro-2-phenyl-3 (2H) -pyridazinone 4,5-dimethoxy-2-phenyl-3 (2H) -pyridazinone 4 _J 5-DImethoxy-2 -cyclohexyl-3 (2H) -pyridazinone

4,5-dimethoxy-2- (3-trifluoromethylphenyl) -3 (2H) -pyridazinone

5-Methoxy-4-chloro-2- (3-trifluoromethyl-phenyl) -3 (2H) -pyrida-15-zinone

5-Amino-4-bromo-2- (3-methylphenyl) -3 (2H) -pyridazinone 3- (1-Methylethyl) -1H-2, 1 _J 3-benzothiadiazine-4 (3H) -one-2,2 -

dioxide and salts

3- (l-methylethyl) -8-chloro-lH-2 _i l, 3-benzothiadiazin-4 (3H) -20. -one-2,2-dioxide and salts

3- (1-methylethyl) -8-fluoro-1H-2, 1 ₎ 3-benzothiadiazine-4 (3H) -

-one-2,2-dioxide and salts

3- (l-methylethyl) -8-methyl-lH-2 _i l, 3-benzothiadiazin-4 (3H) -

-on-2,2-dioxide and salts 25

1-methoxymethyl-3- (1-ethylethyl) -2,1,3-benzothiadiazine

-4 (3H) -one-2,2-dioxide

l-methoxymethyl-8-chloro-3- (l-methylethyl) -2, l, 3-benzothia-

diazin-4 (3H) -one-2,2-dioxide '30 1-methoxymethyl-8-fluoro-3- (1-methylethyl) -2,1,3-benzothiazine

diazine-4 (3H) -one-2,2-dioxide

l-cyano-8-chloro-3- (l-methylethyl) -2, l, 3-benzothiadiazine

-4 (3H) -one-2,2-dioxide

1-cyano-8-fluoro-3- (1-methylethyl) -2,1,3-benzothiadiazine.35-4 (3H) -one-2,2-dioxide

240232 A

- 35 - 0.2. 0050/35177

^f "1-cyano-8-methyl-3- (1-niethylethyl) -2- _J , 3-benzothiadiazine-4 (3H) -one-2,2-dioxide

l-cyano-3- (l-methylethyl) -2, l ₁ 3-benzothiadiazin-4 (3H) -one 2,2-dioxide

1-azidomethyl-3- (1-methylethyl) -2,1,3-thiadiaz benzo home -4 (3H) -one-2,2-dioxide '.

3- (1-methylethyl) -1H- (pyridin-C3,2-e] 2, 1,3-thiadiazine - (4) -one-2,2-dioxide

IQ N- (1-ethylpropyl) -2,6-dinitro-3,4-dimethylaniline N- (1-methylethyl) -ir-ethyl-2 _J 6-dinitro-4-trifluoromethyl-

-aniline

Nn-propyl-N-beta-chloroethyl-2 _} 6-dinitro-4-trifluoromethyl

aniline ^ 5 N-n-propyl-N-cyclopropylmethyl-2,6-dinltro-4-trifluoro-

methyl-aniline

N-bis (n-propyl) -2,6-dinitro-3-amino-4-trifluoro ^> methyl

aniline

N-bis (n-propyl) -2,6-dinitro-4-methylaniline 2Q N-bis (n-propyl) -2,6-dinitro-4-methylsulfonyl-aniline N-bis (n-propyl) - 2,6-dinitro-4-aminosulfonyl aniline-bis (.beta.-chloroethyl) _i 6-dinitro-4-methyl-aniline, N-ethyl-N- (2-methylallyl) -2,6-dinitro-4-trifluoraiethyl -2 -

-aniline

N-methylcarbamic acid 3j-4-dichlorobenzyl ester N-methylcarbamic acid 2,6-di (tert-butyl) -4-methylphenyl

esters

N-phenyl carbamic acid isopropyl ester

3Q N-3-FluoΓpheήylcaΓbamic acid 3-methoxy-2-p-phenol N-chlorophenylcarbamic acid isopropyl ester N-3-chlorophenylcarbamic acid-butyn-1-yl-3-ester N-3-chlorophenylcarbamic acid 4-chloro-2-yl Methyl N-3,4-dichlorophenylcarbamate N- (4-amino-benzenesulfonyl) -carbamic acid, Niethylester

240232 ά ~ ³⁶ ~ ° * ² * ^{οο5ο / 35177}

* "O-i-N-phenylcarbamoyl-propanone oxine N-ethyl-2- (phenylcarbamoyl) -oxypropionic acid amide 3'-N-isopropyl-carbamoyloxy-propionic acid anilide

Ethyl-N- (3- (N'-phenylcarbamoyloxy) phenyl) carbamate 'methyl-N- (3- ^{(N-methyl-N'T-phenylcarbamoyloxy)} phenyl) -

carbamate

Isopropyl N- (3- (N'-ethyl-N'-phenylcarbamoyloxy) -phenyl) - carbo-bamate methyl-N-O-CN'-S-methylphenylcarbamoyloxy-1-phenyl) '-

carbamate

Methyl-N- (3- (N'-4-fluorophenylcarbamoyloxy) -phenyl) -

carbamate

Methyl N- (3- (N'-3-chloro-4-fluorophenylcarbamoyloxy) - phenyl) carbamate

Ethyl N- (3-N ^T -3-chloro-4-fluorophenylcarbamoyloxy) -phenyl) -

carbamate

Ethyl N- (3-N ^f -3 j 4-difluoro-rphenylcarbamoyloxy) -phenyl) -carbamate Methyl-N- (3- (N ^f -3,4-difluorophenylcarbamoyloxy) -phenyl) -carbamate

N-S-i ^ -PluorphenoxycarbonylaminoJ-phenylcarbaminsäure-

methyl ester

N-3- (2-methylphenoxycarbonylamino) -phenylcarbamic acid ethyl ester

N-3- (4-Fluorphenoxycarbonylamino) -phenylthiolcarbaminsäure-

methyl ester

Methyl N-3- (2,4,5-trimethylphenoxycarbonylamino) phenylthiolcarbamate N-3- (phenoxycarbonylamino) -phenylthiolcarbamic acid-methyl-

ester

N, -diethyl-thiolcarbamic acid p-chlorobenzyl ester N, N -di-n-propyl-thiocarbamic acid ethyl ester N, N-propyl-thiolcarbamic acid N-propyl-n-propyl-thiolcarbamate

240232 4 - 37 - ° - ² ·; ΌΟ5Ο / 35177

* "N, N-Di-isopropyl-thiocarbamic acid-2 _J 3-dichloroallyl ester N, N-di-isopropyl-thiocarbamic acid 2,3,3-trichloroallyl

ester

NiN-diisopropyl-thiolcarbamic acid S-methyl-S-isoxazolyl-5-methyl ester

Njn-DI-isopropyl-thiolcarbaminsäure-S-ethyl-S-isoxazolyl

methyl ester

Ethyl N, N-di-sec-butyl-thiocarbamate TijU-1D-sec-butyl-thiolcarbaninic acid benzyl ester N-ethyl-N-cyclohexyl-thiocarbamic acid ethyl ester N-ethyl-N-bicyclo-C 2,2,1] -hept yl-thiolcarbaminsäureethylester

S- (2,3-dichloroallyl> - (2,2,4-trlmethyl-azetidin) -l-carbo-

Tiolate S- (2,3,3-trichloroallyl) - (2,2,4-trimethyl-azetidine) -l-carbothiolate

S-ethyl-hexahydro-1-H-azepine-1-carbothiolate S-benzyl-3-methylhexahydro-1-H-azepine-1-carbothiolate

S-Benzyl-2,3-diniethylhexahydro-1-H-azepine-1-carbothlolate 20 S-ethyl-3-niethylhexahydro-1-H-azepine-1-carbothiolate

N-ethyl-N-n-butyl-thiolcarbamic acid n-propyl ester N, N-dimethyl-dithiocarbamic acid 2-chloroallyl ester N-methyl-dithiocarbamic acid sodium salt Trichloroacetic acid sodium salt Alpha, alpha-dichloropropionic acid sodium salt Alpha, alpha-dichlorobutyric acid, sodium salt

Alpha, alpha, beta, beta-tetrafluoropropionic acid sodium salt alpha-methyl, alpha, beta-dichloropropionic acid sodium salt

^ 3 alpha-chloro-beta- (4-chlorophenyl) -p-ropionic acid methyl ester alphajbeta-di-chloro-beta-phenylpropionic acid methylestec · benzamido-oxy-acetic acid

2,3,5-triiodobenzoic acid (salts, esters, amides)

2,3,6-trichlorobenzoic acid (salts, esters, amides)

35 2,3,5-hexachlorobenzoic acid (salts, esters, amides)

24 02 3 2 A -38.

0050/35177

2-Methoxy-3,6-dichlorobenzoic acid (salts, esters, amides) 2-Methoxy-3,5,6-trichlorobenzoic acid (salts, esters, amides) 3-Amino-2,5,6-trichlorobenzoic acid · (salts, esters , Amides) OjS-dimethyl-tetrachloro-thioterephthalate dimethyl-2,3,5,6-tetrachloro-terephthalate disodium-3,6-endoxohexahydrophthalate 4-amino-3,5,6-trichloro-picolinic acid (salts) 2- Cyan-3- (N-methyl-N-phenyl) -amino-acrylic acid ethyl ester 2-C4- (4'-chlorophenoxy) -phenoxy] -propionic acid isobutyl ester 2-C4- (2 ^f , 4 ^r -dichlorophenoxy) -phenoxy] -propionic acid methyl ester

2-C 4- (4'-trifluoromethylphenoxy) -phenoxy] -propionic acid methyl ester 2-C 4- (2'-chloro-4'-trifluorophenoxy) -phenoxy] -propionic acid

15 sodium salt

2-C 4- (3 ', 5'-dichloropyridyl-2-oxy) -phenoxy] -propionic acid sodium salt

2- (N-benzoyl-3,4-dichloro-phenylamino) -propionic acid ethyl ester

2- (N-Benzoyl-3-chloro-4-fluoro-phenylamino) -propionic acid methyl ester

2- (N-benzoyl-3-chloro-4-fluoro-phenylamino) -propionsäureisopropylester

2-Chloro-4-ethylamino-6-isopopylamino-1,3,5-triazine 2-chloro-4-ethylamino-6- (amino-2'-propionitrile) -l, 3,5-

triazine

2-chloro-4-ethylamino-6-2-methoxypropyl-2-amino-1,3,5-triazine

2-chloro-4-ethylamino-6-butyn-1-yl-2-amino-1 _J 3j5-triazine 2-chloro-4,6-bisethylamino-1, 3,5-triazine 2-chloro-4,6- _{bisisopropylamino-l}} 3,5-triazine 2-chloro-4-isopropylamino-6-cyclopropylamino-l, 3,5-triazin '

240232 A

- 39 - ° · ² · 0050/35177

2-azido-4-methylamino-6-isopropylamino-1, 3,5-triazine 2-methylthio-4-ethylamino, 6'-isopropylamino-1, 3,5-triazine 2-methylthio-4-ethylamino-6 tert -butylamino-1- _J 3,5-triazine 2-methylthio-4,6-bisethylamino-1,3,5-triazine. 2-methylthio-4,6-bisisopropylamino-l, 3,5-triazine

_{2-methoxy-4-ethylamino-6-isopropylamino-l}} 3,5-triazine 2-methoxy-4,6-bisethylamino-l _J 3,5-triazin-Ii We tlioxy-4 fb -TsTs LSOP r op yl amino -1,3, "r 5 -1 iazln 4-amino-6-tert-butyl-3-methylthio-4 _J 5-dihydro-l, 2 _J 4

triazine-5-one

4-amino-6-phenyl-3-methyl-4,5-dihydro-l _J, 2,4-triazin-5-one 4-Isobutylidenamino-6-tert-butyl-3-methylthio-4 _J-dihydro-5 - l, 2,4-triazin-5-one 1-methyl-3-cyclohexyl-6-dimethylamino-1, 3 _J 5-triazine-2,4-

-dione

3-tert-butyl-5-bromo-6-methyluracil Sö

3- (2-Tetrahydropyranyl) -5-chloro-6-methyluracil 3- (2-tetrahydropyranyl) -5j6-trimethyleneuracil

2-methyl-4- (3'-trifluoroniiethylphenyl) -tetrahydro-l _} 2 ₎ 4-

-oxadiazin-3,5-dione

2-methyl-4- (4'-fluorophenyl) tetrahydro-l, 2,4-oxadiazinetrione

-3,5-dione 20 3-amino-l, 2,4-triazole

l-Allyloxy-1- (4-bromophenyl) -2- [l, 2 ', 4 ^r -triazolyl (l') -] -

ethane (salts)

l- (4-chloro-phenoxy ^k 3 ₃ 3 diiiethyl-l (lH-l, 2 _J 4-triazol-l-yl) -

-2-butanone

35 N, N-Diallylchloroacetamide u

2 Λ O 2 3 2 4 '" ⁴⁰ "°' ² "°° 5 ° / 35177

* "N-Isopropyl-2-chloroacetanilide N- (1-methyl-propyn-2-yl) -2-chloroacetanilide

2-Methyl-6-ethyl-N- (propargyl) -2-chloroacetanilide 2-Methyl-6-ethyl-N ~ (ethoxymethyl) -2-chloroacetanilide

2-methyl-6-ethyl-N- (2-methoxy-l-methylethyl) -2-chloracet-

anilide

2-methyl-6-ethyl-N- (isopropoxycarbonylethyl) -2-chloracet-

IQ - 2-methyl-6-ethyl-N- (4-methoxypyrazol-1-ylmethyl) -2-chloro-acetanilide

2-methyl-6-ethyl-N- (pyrazol-1-ylmethyl) -2-chloroacetanilide 2,6-dimethyl-N- (pyrazol-1-ylmethyl) -2-chloroacetanilide 2,6-dimethyl N- (4-methyl-pyrazol-l-yl-methyl) -2-chloro-

^ 5 acetanilide

2,6-Dimethyl-N- (1 _J 2,4-triazol-1-ylmethyl) -2-chloroacetanilide

2,6-dimethyl-N- (3,5-dimethylpyrazol-l-yl-methyl) -2-chloroacetanilide

2Q 2,6-dimethyl-N- ( _1J 3-dioxolan-2-ylmethyl) -2-chloroacatanilide

2,6-dimethyl-N- <2-methoxyethyl) -2-chloroacetanilide 2,6-dimethyl-N- (isobutoxymethyl) -2-chloroacetanilide 2,6-diethyl-N- (methoxymethyl) -2-chloroacetanilide 2.6 diethyl-N- (n-butoxymethyl) -2-chloroacetanilide

2,6-Diethyl-N- (ethoxycarbonylmethyl) -2-chloroacetanilide 2,3,6-trimethyl-N- (pyrazol-1-yl-methyl) -2-chloroacetanilide 2 _> 3-dimethyl-N- (isopropyl) - 2-Chloroacetanilide 2 _J 6-Diethyl-N- (2-n-propoxyethyl) -2-chloroacetanilide

2- (2-Methyl-4-chlorophenoxy-N-methoxy-acetamide 2- (alpha-naphthoxy) -N, N-diethyl-propionamide 2 _, 2-diphenyl-N, N-dimethylacetamide

Alpha (3,4,5-tribromopyrazol-1-yl) -N, N-dimethylpropionamide 35 N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide

240 23 2 4 - «-

0050/35177

NI-Naphthylphthalamic acid Propionic acid 3,4-dichloroanilide Cyclopropanecarboxylic acids, 4-dichloroanilide Methacrylic acid-3 »4-dichloroanilide 2-Methylpentanecarboxylic acid 3,4-dichloroanilide 5-Acetamido-2 _J 4-dimethyltrifluoromethane-sulfonanilide S-Acetamido-methyl-trifluoromethane -sulfonanilid

"2 ^ r oplonyl- amino" ⁵ * -melfnyl · ^ -cnl. ο r- ⁵ 0- (methylsulfonyl) polyglycolic-N-ethoxymethyl-2,6-dimethyl-

anilide

O-CMethylaminosulfonyD-glycolic acid N-isopropylanilide O- (i-propylaminosulfonyl) -glycolic acid-N-butyn-1-yl-3-anilide O-CMethylaminosulfonyD-glycolead hexamethylene amide

15 2,6-dichloro-thiobenzamide 2,6-dichlorobenzonitrile

3,5-Dibromo-4-hydroxybenzonitrile (salts) 3,5-Diiodo-4-hydroxybenzonitr11 (salt e) 3> 5-dibromo-4-hydroxy-0-2,4-dinitrophen.ylbenzaldox: Lm (salts) 3> 5-dibromo-4-hydroxy-0-2-cyano-4-nltrophenylbenzaldoxime

(Salts)

Pentachlorophenol sodium salt

2,4-dichlorophenyl-4'-nitrophenyl ether 2 _J 4,6-trichlorophenyl-4'-nitrophenyl ether 2-chloro-4,6-dichlorophenyl-4'-nitrophenyl ether 2-chloro-4-trifluoromethylphenyl 1-4'- nltrophenylether ^f 2,4 dinitro-4-trifluoromethyl-diphenyl ether 2,4-dichlorophenyl-3'-methoxy-4'-nitro-phenyl ether 2-chloro-4-trifluoromethylphenyl-3'-ethoxy-4'-nitro-phenyl ether

2-Chloro-4-trifluoromethylphenyl-3'-carboxy-4- ^T- nitro-phenyl ether (salts)

2,4-dichlorophenyl-3'-methoxycarbonyl-4'-nitro-phenyl ether 2- (3,4-dichlorophenyl) -4-methyl-1,4-oxadiazolidine-3,5-dione

240232 A : - «- ^oz

0050/35177

2- (3-tert, butyl carbamoyl-oxyphenyl) -4-methyl-l, 2,4-oxadiazinetrione

zolidln-3,5-dione

2- (3-iso-propylcarbamoyl-oxyphenyl) -4-methyl-1,2,4-oxadiazinetrione

zolidine-3,5-dione 2-phenyl-3, 1-benzoxazinone- (4)

(4-bromophenyl) -3,4,5,9, 10-pentaazatetracyclo-C 5,4,1, O ^{2> 6} > 0,

8J ^{1: L} ] -dodeGa-3,9-dlen

2-ethoxy-2,3-dihydro-3IS-dimethyl-S-benzofuranyl methane

- Solvent 10 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl-dimethyl-

-aminosulfonat

_> 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl- (N-methyl)

-N-acetyl) -aminosulfonate 3,4-dichloro-1,2-benzisothiazole N-4-chlorophenyl-allyl-succinic acid imide 2-methyl-4,6-dinitrophenol (salts, esters) 2-sec.Buty1-4, β-dinitrophenol (Salts,) 2-sec.butyl-4,6-dinitrophenol-acetate 2-tert-butyl-4,6-dinitrophenol-acetate 2-tert.butyl-4, β-dinitrophenol (salts) 2-tert.butyl 5-methyl-4,6-dinitrophenol (salts) 2-tert-butyl-5-methyl-4,6-dinltrophenol acetate

2-sec. Amy1-4, β-dinitrophenol (salts, esters)

25 L- (Alpha, alpha-dimethylbenzyl) -3- (4-methylphenyl) -urea l -phenyl-3- (2-methylcyclohexyl) -urea l -phenyl-l-benzoyl-3,3-dlmethylurea l- (4-chlorophenyl) -1-benzoyl-3,3-dimethyl-urea 1- (4-chlorophenyl) -3,3-dimethyl-urea

30- (4-Chloro-phenyl) -3-methyl-3-butyn-1-yl-3-urea 1- (3,4-dichlorophenyl) -3,3-dimethyl-urethane-t-butyl (3,4-dichlorophenyl) ) -l-benzoyl-3,3-dimethyl-urea 1- (3j-4-chloro-phenyl) -3-methyl-3-n-butyl-urea 1- (4-i-propyl-phenyl) -3,3-dimethyl-urea

~ 1- (3-trifluoromethylphenyl) -3,3-dimethylurea

240232 4 -43- · ° · ² · 0050/35177

* "1- (3-alpha, alpha, beta, beta-tetrafluoroethoxyphenyl) -3,3-dimethyl-urea

1- (3-tert-Butylcarbamoyloxy-phenyl) -3,3-di-methyl-urea 1- (3-chloro-4-methyl-phenyl) -3,3-dimethyl-urea 1- (3-chloro-4-methoxyphenyl ) -3,3-dimethyl-3-naphtha 1- (3,5-dichloro-4-methoxyphenyl) -3,3-dimethyl-urea 1- [4 (4'-chlorophenoxy) -phenyl] -3,3-dimethyl- urea 1-C 4 (4'-methoxyphenoxy) -phenyl] -3,3-dimethyl-urea 1-cyclooctyl-3,3-dimethyl-urea 1- (hexahydro-4,7-methan-indan-5-yl) -3 , 3-dimethyl-urea 1_ [1- or 2- (3a, 4,5,7,7a-hexahydro) -4,7-methanoindanyl] -3,3-dimethyl-urea

l-phenyl-S-methyl-S-methoxy-urea

1- (4-chlorophenyl) -3-methyl-3-methoxy-urethane t-butyl- (4-bromophenyl) -3-methyl-3-niethoxy-urea 1-C3-4-dichlorophenyl-3-methyl-3- methoxy-urea 1- (3-chloro-4-b-phenyl) -3-methyl-3-niethoxy-urea 1- (3-chloro-4-isopropyl-phenyl) -S-methyl-S-methoxy-urea 1- (3-chloro-4-bis-phenyl) -3- chloro-4-methoxyphenyl) -3-methyl-3-methoxy-urea l- (3-tert-butylphenyl) -3-methyl-3-methoxy-urea l- (2-Benzthlazolyl) -l _i 3-dlmethyl-urea 1- (2-Benzothiazolyl) -3-methyl-urea 1- (5-trifluoromethyl-1,3,4-thiadiazolyl) -1,3-dimethyl

25 -urea

Imidazolidin-2-one-1-carboxylic acid isobutylamide 1,2-Dimethyl-3,5-diphenylpyrazolium methylsulfate 1,2-4-trimethyl-3,5-diphenylpyrazolium methylsulfate l, 2-dimethyl-4-bromo -3,5-diphenylpyrazolium methylsulfate 1,3-dimethyl-4- (3,4-dichlorobenzoyl) -5-C (4-methylphenylsulfonyl) -oxy] -pyrazole 2,3,5-trichloropyridinol- (4)

1-methyl-3-phenyl-5- (3'-trifluoromethylphenyl) -pyridone- (4) 1-methyl-4-phenyl-pyridinium chloride

35 1,1-dimethylpyridiumium chloride

240232 4 -44- ° * ² -

0050/35177

* "3-phenyl-4-hydroxy-6-chloropyridazine 1,1'-dimethyl-4,4 ^! -Dipyridylium-di (methylsulfate)

1.1 · di (3 _J 5-dimethylmorpholine-carbonylmethyl) -4,4'-di-

pyridylium dichloride 5 1,1'-ethylene-2,2'-dipyridylium dibromide

3- [l (N-ethoxyamino) -propylidene] -6-ethyl-3,4-dihydro-2-H-

-pyran-2,4-dione

3- [1- (N-Allyloxyamino) -propylidene] -6-ethyl-3,4-dihydro-2-H-pyran-2,4-dione 2- [1- (N-allyloxyamino) -propylidene] - 5,5-dimethylcyclohexan-

-1,3-dione (salts)

2-Cl- (N-Allyloxyamino-butylidene] -5,5-dimethylcyclohexan-

-1,3-dione (salts)

2-Cl-CN-Allyloxyamino-butylidene] -5,5-dimethyl-4-methoxycarbonyl-cyclohexane-1-dione (salts)

2-chlorophenoxyacetic acid. (Salts, esters, amides)

4-chlorophenoxyacetic acid (salts, esters, amides)

2,4-diclorophenoxyacetic acid (salts, esters, amides)

2,4,5-trichlorophenoxyacetic acid (salts, esters, amides) 2-methyl-4-chlorophenoxyacetic acid (salts, esters, amides) 3,5j6-trichloro-2-pyridinyl-oxyacetic acid (salts, esters,

amides)

Alpha Naphthoxyessigsäuremethylester

2- (2-Methylphenoxy) propionic acid (salts, esters, amides) 2- (4-chlorophenoxy) propionic acid (salts, esters, amides) 2- (2,4-dichlorophenoxy) propionic acid (salts, esters, amides) 2- (2,4,5-trichlorophenoxy) -propionic acid (salts, esters, amides)

2- (2-methyl-4-chlorophenoxy) -propionic acid (salts, esters, amides)

4- (2,4-dichlorophenoxy) -butyric acid (salts, esters, amides) 4- (2-methyl-4-chlorophenoxy) -butyric acid (salts, esters, amides)

35 gyclohexyl-3- (2,4-dichlorophenoxy-acrylate

24 02 3 2 4: - · ₅ -

0050/35177

9-Hydroxyfluorene-carboxylic acid (9) (salts, esters)

2,3,6-trichlorophenyl-acetic acid (salts, esters) - 4-chloro-2-oxo-benzothiazolin-3-yl-acetic acid (salts,

Ester) 5 Gibelleric acid (salts) Disodium methylarsonate

Monosodium salt of methylarsonic acid N-phosphono-methyl-glycine (salts) N, N-bis (phosphonomethyl) -glycine (salts) 2-Chloroethanephosphonic acid 2-chloroethyl ester Aammonium ethylcarbamoyl-phosphonate Di-n-butyl-1-butylamino cyclohexyl-phosphonate

Trithlobutylphosphit

0,0-Dlisopropyl-5- (2-benzosulfonylamino-ethyl) phosphorodithioate

2,3-Dihydro-5,6-dimethyl-1,4-dithiin-1,1- k, 4-tetraoxide 5-tert-butyl-3- (2,4-dichloro-5-isopropoxyphenyl) -l, 3 , 4-

-oxadiazolon- (2)

4,5-Dichloro-2-trifluoromethyl-benzimidazole (salts) 1,2,3,6-tetrahydropyridazine-3,6-dione (salts)

Succinic mono-N-dimethylhydrazide (salts)

(2-Chloroethyl) -trimethyl-ammonium chloride (2-methyl-4-phenylsulfonyl) trifluoromethanesulfonanilide 1, l-dimethyl-4,6-diisopropyl-5-indanyl ethyl ketone sodium chlorate

Ammonium rhodanide calcium cyanamide

2-Clilor-4-trifluoromethylphenyl-3'-ethoxycarbonyl-4'-nitro-

20 phenyl ether.

1- (4-Benzyloxyphenyl) -3-methyl-3-methoxyurea 2- [1- (2,5-Dimethylphenyl) ethylsulfonyl] -pyridine N-oxide 1-acetyl-3-anilino-4-methoxycarbonyl-5 Methylpyrazole 3-Anilino-4-methoxycarbonyl-5-methylpyrazole 3-tert-butylamino-4-methoxycarbonyl-5-methylpyrazole

24 02 3 2 k '-> * - α *.

0050/35177

N-Benzyl-N-isopropyl-trimethylacetamide

2- [4- (4'-chlorophenoxymethyl) -phenoxy] -propionsäuremethyl-

ester

2- [4- (5-bromopyridyl-2-oxy) -phenoxy] -propionic acid ethyl ester

2- [4- (5'-Iodpyridyl-2-oxy) phenoxy] -propionsäureethyl-

ester

2- [4- (5'-iodopyridyl-2-oxy) -phenoxy] -propionic acid n-butyl ester 2-chloro-4-trifluoroethylphenyl-3 ^f - (2-fluoroethoxy) -4 ^f -netrithin

phenyl ether

2-chloro-4-trifluoromethylphenyl-3- (ethoxycarbonyl) -iiiethyl-

thio-4-nitrophenyl ether

2,4,6-trichlorophenyl-3- (ethoxycarbonyl) methylthio-4-nitrophenyl ether

2-C1- (N -ethoxy) -butylidene] -5- (2-ethyl-thiopropyl) -3-

-hydroxy-cyclohexene (2) -one- (l) (salts)

2-C1 (N-Ethoxamino) -butylidene] -5- (2-phenylthiopropyl) -3

-hydroxy-cyclohexene (2) -one- (l) (salts)

4-C 4- (4'-trifluoromethyl) -phenoxy] -pentene-2-carboxylic acid

ethyl ester

2-chloro-4-trifluoromethyl-3 ^f methoxycarbonyl-4'-nitrophenyl ether, 2,4-dichlorophenyl-3'-carboxy-4 ^f -nitrophenylether (salts) of 4,5-dimethoxy-2- (3-alpha-alpha beta-trifluoro-beta-bromoethoxy

phenyl) -3- (2H) -pyridazinone

2,4-dichlorophenyl-3'-ethoxy-ethoxy-ethoxy-4'-nitrophenyl-ether 2,3-dihydro-3,3-dimethyl-5-benzofuranylethanesulfonate N- (4-methoxy-6-methyl- 1 _J 3,5-triazin-2-yl-aminocarbonyl) -2-

-chlorbenzolsulfonamid

l- (3-chloro-4-ethoxyphenyl) -3,3-dimethylurea

2-Methyl-4-chlorophenoxy-thioacetic acid ethyl ester 35. 2-Chloro-3,5-diiodo-4-acetoxy-pyridine

240232 4 '.- »-

° · ² - 0050/35177

"l-t4- [2- (4-methylphenyl) -ethoxy] -phenyl} -3-methyl-3-methoxy

oxyurea

2,6-Dimethyl-N- (pyrazol-1-yl-methyleneoxymethyl) -2-chloroacetanilide 2-Methyl-6-ethyl-N- (pyrazol-1-yl-methyleneoxymethyl) -2-chloro

acetanilld

l - (- Alpha-2,4-dichlorophenoxypropionic acid) -3- (0-methylcarba-

Moyles) -anilld

l- (alpha-2-bromo-4-c'hlorplienoxypropionsäure ^':) -l-CD-meTrhylcarbamoyD anilide

2-methyl-6-ethyl-N- (pyrazol-l-yl-ethylenoxymethyl) -2-chloro-

acetanilide

Methyl-N-chloro-chloro-n-methylsulfenyl-CS-CN'-dichlorofluoromethylsulfenyl-N ^T -phenylcarbamoyl-oxy) -phenyl] -carbamate Methyl-N-dichlorofluoromethylsulfenyl- [3 - (N'-dichlorofluoromethylsulfenyl-N'-3-niethylphenylcarbamoyl-oxy) phenyl] -

carbamate

N- (pyrazol-1-ylmethyl) -pyrazol-1-yl-acetic acid-2,6-dimethylanilide N- (pyrazol-1-ylmethyl) -1, 2,4-triazol-1-yl-acetic acid -2,6

-d methylanilide

2- (3-trifluoromethylphenyl) -4 H -3,1-benzoxazin-4-one 2- (2-thienyl) -4 H-3, 1-benzoxazin-4-one 2- (3-pentafluoroethoxyphenyl) -4 H-3, l-benzoxazin-4-one 2- (3-trifluoromethylthio-phenyl) -4H-3,1-benzoxazin-4-one 2- (3-difluoro-chloromethoxyphenyl) -4H-3) -1-benzoxazin-4-one

5-Nltro-2- (3-trifluoromethylphenyl) -4H-3, 1-benzoxazin-4-one * "'5-chloro-2- (3-trifluoromethoxyphenyl) -4H-3, 1-benzoxazine-4 on 5-chloro-2 - [(3-alpha-alpha-beta-beta) -tetrafluoroethoxyphenyl] -

-4H-3, l-benzoxazin-4-one

5-Pluor-2 - [(3-alpha-alpha-beta-beta) -tetrafluoroethoxyphenyl] -4H-3,1-benzoxazin-4-one 5-chloro-2- (4-difluorochloromethoxyphenyl) -4H-3 l-benzoxazin-4-one

240232

- 48 - ^{0 <£} · 0050/35177

^ 5-Fluoro-2- (4-difluoro-chloronethoxyphenyl) -4H-3, 1-benzoxazine

-4-one

5-Fluoro-2- (phenyl) -4H-3, 1-benzoxazin-4-one 5-Fluoro-2- (3-difluoromethoxyphenyl) -4H-3, 1-benzoxazin-4-one 5-Chloro-2 (phenyl) -4 H-3, 1-benzoxazin-4-one 3- (3,5-dichlorophenyl) -4-methoxycarbonyl-5-methylpyrazole 3- (3-quinopropyl) -4-methylthoxycyclobenzene 1-5- me thylρ yrazo1 3- (3-fluorophenyl) -4-methoxycarbonyl-5-methylpyrazole l -acetyl-3-C3-nophenyl) -p-thoxycarbonyl-methyltetrapyrazole

l-Acetyl-3- (3-chlorophenyl) -4-methoxycarbonyl-5-methyl-

pyrazole

1-Acethyl-3- (3-b-romphenyl) -4-methoxycarbonyl-5-methyl-

pyrazole

l-acetyl-3- (3,5 ^<äichlor> phenyl) -4-methoxycarbonyl-5-ever thylpyrazol

l-Acetyl-S-thienyl-methoxycarbonyl-S-methylpyrazole N-3-chloro-4-isopophenylphenyl thiolcarbamic acid methyl ester N-methyl-S-methyl-fluoro-phenyl-thiocarbamate N-3-chloro-4-isopentyl-phenyl-thiolca-bam-acid methylene

ester

N-3-ChlOΓ-4-difluoro-methoxyphenyl-thiolcaΓbamic acid methyl ester N-3-chloro-4- (1-chloroisopropyl) -phenyl-thiocarbamic acid

methylester

l- (2-pl, rophenyl) -S-

1- (3-Isopropylphenyl) -3-methyl-5-iminolimidazolidin-2-one 1- (4-isopropylphenyl) -3-methyl-5-iminoimidazolidin-2-one 1-C3-C1,1 * 2,2- tetrafluoroethoxy) phenyl] -3-methyl-5-lminoimidazolidin-2-one

l- (3 ₁ 4-dichlorophenyl) -3-methyl-5-iminoimidazolidine-2-one

1- (3,4-Difluorophenyl) -3-methyl-5-iminoimidazolidin-2-one 35

24023 2 U -W- ^oz

OQ5O / 35177

1,1-dioxide

6-methyl-3-methoxy-5 _i 6-dihydro-l, 2 _J 4,6-thiatriazine-5-one 1,1-dioxide sodium salt -

  1,1-dioxide

6-methyl-3-ethoxy-5,6-dihydro-l, 2,4,6-thiatriazine-5-one

1,1-dioxide

6-n-Propyl-3-ethoxy-5,6-dihydro-l, 2,4, β-thiatriazin-5-one, -1,1-dioxide sodium salt '

δ-methyl-S-isopropoxy-Sβ-dihydro-l, 2,4,6-thiatriazazin-5-one

1,1-dioxide

on-Propyl-S-isopropoxy-S, 6-dihydro-l, 2,4,6-thiatriazin-5-one-1,1-dioxide 6-isopropyl-3-sec: - butoxy-5 »6- dihydro-1,2,2 _i 4 _J 6-thiatriazine-5

-on-1, l-dioxide sodium salt

N-3 '- (2 "-chloro-4' trifluoromethylphenoxy) -6'-nitrobenzoyl

anthranilic acid e

N-3 ^T - (2 "-chloro-4-trifluoromethylphenoxy ^ff) -6'-nitrobenzoylanthranilsäuremethylester

^N-f 3 - (2 "-chloro-4 ^tt trifluoromethylphenoxy) -6 ^t -nitrobenzoyl-

anthranilic acid sodium salt

^N-f 3 - (2 "-chloro-4 'trifluoromethylphenoxy) -6 ^T -nitrobenzoyl- -3-chloroanthranilic acid N-3 ¹ - (2"-chloro-4' trifluoromethylphenoxy) benzoyl-3-chloro-

anthranilic

N-3 '- (2' -chloro-4 ^f "trifluoromethylphenoxy) benzoyl-3-methyl

anthranilic

N-3 '- (2 "-chloro-4' trifluoromethylphenoxy) -benzoylanthranilsäure

N-3 '- (2 ", 4" -Dichlorphenoxy) -6'-nitrobenzoylanthranilsäure

N- [3 '- (2-chloro ^{lt-4' T-trifluoromethylphenoxy)} -6 ^T -nitrophenyl] -4H-1,3-benzoxazin-4-one

^N-t C3 - (2 "-chloro-4" -trifluonnethylphenoxy) -6 ^l -nitro-35 phenyl] -4H-1.3-8-methoxybenzoxazin-4-one

240232 A

- 50 - & -? - 005O / -35-177

* "5-Chloro-2- (3-trifluoro-ethyl-phenyl) -4H-3, 1-benzoxazin-4-one 5-Fluoro-2- (3-trifluoromethyl-phenyl) -4H-3, 1-benzoxazine-4 -on - 5-fluoro-2- (3-cH-fluoro-chlorometh-yl-.phenyl) -4H-3, l-benzoxazine

-4-one

- 5-Chloro-2- (3-difluoro-chloromethyl-phenyl) -4H-3, 1-benzoxazin-4-one

l- [5- (3-i ^I luorbenzylthio) -thiadiazolyl-2] -l-methyl-3-niethylharnstoff

In addition, it is useful to apply the new compounds alone or in combination with other herbicides mixed with other pesticides together, for example, with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used for the elimination of nutritional or trace element deficiencies. To activate the herbicidal action it is also possible to add wetting agents and adhesives as well as non-phytotoxic oils and oil concentrates.

Claims (2)

invention claim R ^{1 is} alkyl of 1 to 4 carbon atoms ρ
R is alkyl of 1 to 4 carbon atoms, Alkenyl having 3 to 4 carbon atoms, alkynyl having 3 to 4 carbon atoms or haloalkenyl having 3 or 4 carbon atoms and 1 to 3 halogen atoms X straight-chain or branched alkylene radical having 1 to 5 carbon atoms, optionally phenyl-substituted η = 0 or 1 Y is a non-aromatic heterocycle having 4 to 7 atoms and no or one double bond in the heterocyclic ring containing 1 or 2 heteroatoms from the group sulfur, nitrogen, oxygen in any order, wherein the heterocycle is optionally substituted by alkyl Z is hydrogen or methoxycarbonyl and the salts of this compound.