DD262573A5 - HERBICIDE MEDIUM - Google Patents

Abstract

The invention relates to herbicidal agents. According to the invention, the active ingredient used in the novel herbicidal compositions is one or more compounds of the formula (I) or salts thereof in which A, ACH 2, S, CHR 4, CR 42, SO or SO 2; B0, S, SO, SO2, CH2, CHR4, CR42, NR5, NCXR5 or NCX2R5; X0 or S; R1Hal, NO2, XH, (substituted) alkyl (oxy or mercapto), cycloalkyl (oxy or mercapto), alkenyl (oxy or mercapto), cycloalkenyl (oxy or mercapto), alkynyl (oxy or mercapto), (substituted) alkoxycarbonyl (oxy or mercapto), alkoxycarbonylmethylamino; R2H or (hydroxy) alkyl; R3H, (substituted) alkyl, cycloalkyl, alkoxycarbonylmethyl, R5, nicotinoyl, 1-imidazolylcarbonyl or a radical of the formulas CX (Z), COCOZ, SOR6, SO2R6, SO2NHR5, SO2N (R5) 2, PX (R7) 2 or COCH2PX (R7) 2; R4 is the meaning of R5, CXR5 or CX2R5; m0, 1, 2, 3, 4 or 5; n0, 1, 2, or 3, as active ingredient (s) included. They are ideal for the control of monocotyledonous or dicotyledonous harmful plants. Formula (I)

Description

Field of application of the invention

The invention relates to herbicidal compositions containing a novel a-lminocarbonsäureaniliden of formula I for use in agriculture.

Characteristic of the known state of the art

Some of these compounds are from Tetrahedron Letters 22 (1981) 2411, Acta Chim. Scand. 11 (1957) 1183 and JP-A 78-31. However, no biological activity of these compounds has been reported.

Object of the invention

The aim of the invention is the provision of new agents with a strong herbicidal action and good compatibility with crops, which are suitable for selective weed control in crops.

Explanation of the essence of the invention

The invention has for its object to find new compounds that act as an active ingredient in herbicidal agents with the

desired properties are suitable.

It has been found that the cyclic α-lminocarbonsäureanilide the following formula I is an excellent herbicidal

Have effect.

According to the invention, compounds of the formula I or their salt are therefore used as the active ingredient in the new herbicidal compositions

(I)

applied, in which

A, A '= independently of one another CH ₂ , S, or one of the two radicals A, A' = CHR ⁴ , C (R ⁴ I ₂ ,> SO or> SO ₂ ,

B = O, S,>SO,> SO, SO ₂ , CH ₂ CHR ⁴ , C (R ⁴ I ₂ ,> NR ⁵ ,> NC = X (R ⁵ ) or NC = X (XR ⁵ ), with the Given that A and B or

A 'and B may not simultaneously be O, S, SO or SO ₂ , X = O or S,

R ¹ = halogen, NO ₂ , (C ₁ -C ₄ ) alkyl, -X (C ₁ -C ₄ ) alkyl or (C ₁ -C ₄ alkoxycarbonyl, where the last three radicals up to

may be substituted six times by halogen or one or two by OH,

(C 3 -C ₆ ) cycloalkyl, (C ₁ -C 12 -alkenyl, (C ₅ -C ₆ ) -cycloalkenyl, (C ₃ -C ₇ ) -alkynyl,

(C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkoxycarbonyl, (C ₁ -C 11 alkoxycarabonyKCi-Csl-alkoxycarbonyl, (d-CelAlkoxycarbonylmethylamino.-XH,

or -XKCi-Cslalkoxycarbonyl], R ² = H, (C ₁ -C ₄ ) alkyl or (C ₁ -C ₆ -hydroxyalkyl,

R ³ = H, (C ₁ -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkenyl, (C ₁ -C ₄ ) halogenoalkyl, (C ₁ -C 18 -alkoxy) -dialkyl, (CC) alkoxycarbonylmethyl,

Phenoxy (C ₁ -C ₄ ) alkyl, nicotinoyl, 1-imidazolylcarbonyl, the meaning of R ⁵ or

X OO

^ Ii ii

a radical of the formula -C or -C-C-Z in which

O X -SN (RS) ₂ , ¹¹ -7-PR ⁷ Il R ⁷

= R ⁶ has the meaning of, or the radical OR ^5, halogen _(Ci-C4) alkyl, (Ci-C ₄₎ alkoxy (Ci-C ₄₎ alkyl, phenoxy (G | _-C4) alkyl, (d- diAlkylamino or phenylamino, wherein the phenyl radical may be substituted by halogen, (Ci-C ₄ ) AIkOXy or (C ₁ -C ₄ ) AlkYl, further means a group of the formulas

0 0 0

H, Il - H c

-SR ⁶ , -SR ⁶ , -S-NHR ⁵ ,

ii

0 0

O X

Ii Il _n

or -C-CH 2 -PR ⁷ ,

R ⁷

R ⁴ = independently of one another R ⁶ , -C = X (R ⁵ ) or-C = X (XR ⁵ ),

R ⁵ = (C, -C ₈ ) alkyl, phenyl, pyridyl or benzyl, both up to three times by (C ₁ -C ₄ ) AlkYl, (Ci-C ₄ ) alkoxy, halogen, CF ₃

or NO ₂ can be substituted,

R ^e = independently of one another H, halogen, OH, the meaning of R ⁵ or the radical OR ⁵ ,

R ⁷ = the meaning of R ⁶ and SH or the radical SR ^S ,

m = 0,1,2,3,4 or 5

η = 0,1,2 or 3

mean.

In the above, halogen preferably denotes F, Cl or Br. (C ₁ -C ₄ ) Haloalkyl represents, for example, the radicals -CF ₃ , -CH ₂ F ₃ , -CHF-CF ₃ , -CF ₂ -CF ₂ Cl, -CF ₂ -CF ₂ H, -CF ₂ -CHFCI or -CF ₂ -CHF-CF ₃ . Halogenated -X (C ₁ -C ₄ ) Alkyl stands in particular for OCF ₃ , OCH ₂ -CF ₃ , -OCHF-CF ₃ , -OCF ₂ CHF ₂ or -OCF ₂ -CHF-CF ₃ . In the case of Z = halogen (C 1 -C ₄ ) alkyl, preference is given to monochloroalkyl radicals in which the chlorine atom is oriented in position C-1 of the alkyl radical.

The abovementioned formula I also includes all optical isomers and mixtures of isomers of the corresponding compounds and their agriculturally acceptable salts. The salt formation can take place on a nitrogen atom of the heterocyclic part or on the carboxylic acid group in the case of R ⁴ = COOH. Suitable salts are the salts customary in agriculture, for. As alkali, alkaline earth, ammonium or substituted ammonium salts. The compounds of the formula I, except those in which

a) A, B and A '= CH ₂ ; X = OjR ¹ = chlorine, methyl, ethyl, ethoxy, n-butoxy; R ² = H; R ³ = methyl, ethyl, n-propyl or n-butyl, (R ") n = H and m = 0,1,2 or 3; 5

b) A, B and A '= CH ₂ ; X = O; R ² = H or C ₂ H ₅ ; R ³ = CH ₃ or CO ₂ CH ₃ ; (R ⁴ ) _n = H or mono-CH ₃ and m = 0;

c) A, B and A '= CH ₂ ; X = O; (R ¹ L = 4-chloro; R ² = H; R ³ = nicotinoyl and (R ⁴ J _n = H; and d) A and A '= CH ₂ ; X = O; (R ¹ L = 4-chloro R ² = H; R ³ = nicotinoyl and (R ⁴ ) _n = H; and

d) A and A '= CH ₂ ; B = 0; X = O; (R ¹ L = H; R ² = H; R ³ = CO ₂ CH ₃ and (R ⁴ J _n = H

applies, are new. These new compounds and their salts are therefore also the subject of the invention.

As radicals of the formula | are preferably in question the piperidine, piperazine, morpholine, tetrahydro-1,4-

thiazine or tetrahydro-1,3-thiazine ring, which may be either unsubstituted or substituted in the manner indicated above, and optionally their sulfoxides or sulfones, where those radicals for which η = O, are particularly preferred. Among the compounds of the formula I, those compounds are to be emphasized in which: A, A ', B = CH ₂ ; X = O, R ¹ = halogen, (C ₁ -C ₄ ) alkoxy, (Cr-Cy) alkynyloxy or (C ₁ -C ₈ ) alkoxycarbonyl (d-cefalkoxycarbonyl; R ² = H, (C ₁ -C ₄ ) alkyl or -CH ₂ OH; R ³ = (C ₁ -C ₄ alkoxycarbonyl, (C ₁ -C ₄ alkoxysulfonyl) OdBrDi (C ₁ -C ₄ ) alkoxyPhOSPhORyl, in particular (d-Q 1 alkoxycarbonyl; m = 1, 2 or 3 and η = O.

In the aniline radical of the compounds of the formula I, preference is given to the substitution in position 2,4 or 5 for the radical R ¹ . The present invention also provides a process for the preparation of the compounds of the formula I or salts thereof, wherein an α-iminocarboxylic acid anilide of the formula II is reacted with a compound of the formula III in the presence of a base and the compound obtained is optionally in the usual manner Salt is transferred.

(R ⁴ ) n

R ³ -Hal (II) (HI)

The reaction is carried out in an inert organic solvent such as diethyl ether, toluene or acetonitrile at temperatures of 0 to 80 ⁰ C, preferably at 20-40 ⁰ C. As the base, tertiary amines such as triethylamine or pyridine or inorganic bases such as alkali metal hydroxide or alkali metal carbonate can be used. The α-lminocarbonsäureanilide of formula II are prepared by reacting an α-lminocarbonsäurehydrochlorids with an aniline

the formula I λ Jni t> ^> on the basis of that of B. afEkenstam (Acta Chim. Scand 11,1183 [1957])

described method produced.

The compounds of the formula I according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants, such as e.g. Avenafatua, Alopecurus, Setaria, Digitaria, Echinochloa, Sorghum, Imperata, Acropyrone, Galium, Amaranthus, Abutilon, Ipomoea, Sinapis, Viola, Lamium, Veronica, Cirsium, Rumex, Sesbania. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It does not matter whether the substances are applied in the pre-sowing, pre-emergence or postemergence process.

If the compounds according to the invention are applied to the surface of the earth before germination, either the emergence of the weed seedlings is completely prevented, or the weeds grow to the cotyledon stage, but then cease their growth and finally die completely after three to five weeks. Upon application of the active ingredients to the green parts of the plants postemergence also occurs very quickly after treatment, a drastic halt in growth, and the weed plants remain in the growth stage present at the time of application or die after a period of time more or less fast, so that on this A harmful to the crops weed competition can be eliminated very early and sustainable by the use of the novel agents of the invention.

Although the compounds of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops such. As wheat, barley, rye, rice, corn, sugar beet, cotton and soy only insignificant or not damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops

Crops.

In addition, the compounds according to the invention have growth-regulatory properties in crop plants.

They regulate into the plant's metabolism and can thus be used to facilitate harvesting such as. B. by triggering desiccation, abscission and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures as it reduces or eliminates storage

can be completely prevented.

The compounds according to the invention can, optionally in admixture with further active components, as a wettable powder, emulsifiable concentrates, sprayable solutions, mordants, dusts, dispersions, granules or microgranules in

the usual preparations are used.

Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance (s) except, if appropriate, a diluent or inert substance or wetting agent such as polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenylsulphonates and / or dispersing aids such as lignosulphonic acid sodium, 2,2 '. -dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or oleoylmethyltaurine acid. The

Production is carried out in the usual manner, for. B. by grinding and mixing of the components.

Emulsifiable concentrates may e.g. by dissolving the active ingredients in an inert organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or aliphatic or cycloaliphatic hydrocarbons with the addition of one or more emulsifiers. In the case of liquid active substances, the proportion of solvent can also be omitted in whole or in part. Ice emulsifiers can be used, for example:

Alkylarylsulfonsaure calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, fatty alcohol-propylene oxide condensation products, alkyl polyglycol ethers, sorbitan fatty acid esters, or Polyoxyethylensorbitansäureester

Polyoxethylensorbitester.

Dusts can be obtained by grinding the active ingredients with finely divided, solid substances, eg. As talc, natural clays, such as

Kaolin, bentonite, pyrophillite or diatomaceous earth obtained.

Granules can be prepared either by spraying the active ingredients on adsorptive, granulated inert material or by applying active ingredient concentrates by means of binders, for. As polyvinyl alcohol, polyacrylic acid sodium or mineral oils on the surface of carriers such as sand, kaolinites or granulated inert material.

Also suitable active ingredients in the usual manner for the production of fertilizer granules - if desired in

Mixture with fertilizers - be granulated.

In wettable powders, the active ingredient concentration is about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation constituents. For emulsifiable concentrates, the concentration of active ingredient may be about 5 to 80% by weight.

Dusty formulations usually contain 0.05 to 20% by weight of active ingredient (s), sprayable solutions about 2 to 20% by weight. For granules, the active ingredient content depends in part on whether the active compound is liquid or solid

and which grinding aids, fillers, etc. are used.

In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing,

Emulsifying, penetrating, solvents, fillers or carriers.

For use, the concentrates present in commercially available form are optionally diluted in the usual manner, for. B.

for wettable powders, emulsifiable concentrates, dispersions and sometimes also for microgranules by means of water.

Dusty and granulated preparations and sprayable solutions are usually not before use

more diluted with other inert substances.

With the external conditions such as temperature, humidity and the like. the required application rate varies. It can vary within wide limits, eg. B. between 0.005 and 10.0 kg / ha or more active substance, but preferably it is between

0.01 and 5kg / ha.

Also, mixtures of the blended formulations with other agents, such. As insecticides, acaricides, herbicides,

Fertilizers, growth regulators or fungicides may be possible.

embodiments

The invention is explained in more detail below with reference to some examples. Below are some formulation examples listed:

Formulation Examples Example 1

A dust is obtained by mixing 10 parts by weight of active compound with 90 parts by weight of talc or another inert substance and comminuting in a hammer mill.

Example 2

A wettable powder easily dispersible in water is obtained by mixing 25 parts by weight of active ingredient, 64 parts by weight of kaolin-containing quartz as an inert, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting and dispersing agent, and grinding in a pin mill.

Example 3

An easily water-dispersible dispersion concentrate is obtained by mixing (about 255 to about 377 ⁰ C boiling range) mixing 20 parts by weight of active ingredient with 6 Gewichtsteiien alkylphenol ^(R Triton X207), 3 parts by weight of isotridecanol polyglycol ether (8EO) and 71 parts by weight of paraffinic mineral oil and in a ball mill milled to a fineness of less than 2 microns.

Example 4

An emulsifiable concentrate is obtained from 15 parts by weight of active compound (s), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol (10EO) as emulsifier.

Chemical Examples Example 1 1-Ethoxycarbonylpiperidine-2-carboxylic acid (2-fluoro-4-chloro-5-methoxy) anilide

To a solution of 3.6 g (13 mmol) of piperidine-2-carboxylic acid (2-chloro-4-fluoro-5-methoxy) anilide and 2.7 g (27 mmol) of triethylamine in 70 ml of toluene is added at room temperature with stirring a solution of 1.5 g (14 mmol) of ethyl chloroformate in 30 ml of toluene was added dropwise. The mixture is stirred for 1 h at room temperature and 2 h at 5O ⁰ C, filtered off with suction from the precipitate and the solution is washed twice with half-concentrated hydrochloric acid and twice with water. It is dried over sodium sulfate, the solvent is distilled off and the residue is dried in vacuo. 4.0 g (86% by weight) of i-ethoxycarbonyl-piperidine-2-carboxylic acid (2-fluoro-4-chloro-5-methoxy) -anilide are obtained as a pale yellow, viscous oil.

Example 2

1-diethoxyphosphoryl-piperidine-2-carboxylic acid (4-chloro) -anilide

To a solution of 3.47 g (14.5 mmol) of piperidine-2-carboxylic acid (4-chloro) anilide and 2.93 g (29 mmol) of triethylamine in 40 ml of acetonitrile is added a solution of 2.50 g (14.5 mmol) of diethyl chlorophosphate in 30 ml of acetonitrile. Man stirs

for three hours at 4O ⁰ C and the mixture is poured into ice water (three times the volume).

Extract with 3 x 100 ml of methylene chloride, wash the combined organic extracts with 2 x 50 ml of 2N HCl and 2 x 50 ml of water and dry over sodium sulfate. After distilling off the solvent, triturating the residue with diisopropyl ether, filtering off with suction and then drying, 3.80 g (70% by weight) of 1-diethoxyphosphoryl-piperidine are obtained.

2-carboxylic acid (4-chloro) -anilide as a light brown powder (mp 169-172T).

EO: ethylene oxide units

Table 1

Compounds of the formula I

r2

(R ⁴ ) n

example

(R ⁴ ) n

A "

Fp [ ⁰ C]

3 4 5 6 7 8

4-Cl H

2-F, 4-Cl, 5-OCH ₃ "

4-Cl "

2-F, 4-Cl, 5-OCH ₃ "

4-Cl "

4-Cl "

4-Cl "

CH ₃ CO-it

C ₂ H ₅ OOC-C ₆ H ₅ CH ₂ OOC-

CH ₂ CH ₂ CH ₂

Il Il Il

LJ

170 oil

60-62

110-115

Continuation Table 1 Example (Rl) _m

Compounds of the formula I

r2 r3 ₍ R4 _{) n}

A ¹

Fp [ ⁰ C]

10 2-F, 4-Cl 5-OCH ₃ H 4-NO ₂ -C ₆ H ₄ CO 11 2-F, 4-Cl 5-OCH ₃ Il C ₆ H ₅ CO- 12 4-Cl, M 4-NO ₂ -C ₆ H ₄ CO 13 4-Cl, Il C ₆ H ₅ CO- 14 4-CF ₃ Il C ₂ H ₅ OOC- 15 2-F, 4-CF ₃ 5-OCH ₃ Il Il 16 4-Cl Il -P- (OH) ₂ 17 2-F, 4-Cl, 5-OCH ₃ Il Il 18 4-Cl Il C ₆ H ₅ -SO ₂ - 19 4-Cl, Il Il 20 4-Cl Il -P ^ OC ₂ H ₅ CH ₃

CH ₂ CH ₂ CH ₂ O

Il Il Il Il

180-185 74-78 61-63 Oil

21 2-F, 4-Cl, 5-OCH ₃

ro σ> ro

Continued Table Example (R ¹ J _1n

Compounds of the formula IR ² R ³ (R ⁴ ) _n ^A

A ¹

Fp [ ⁰ C]

22 4-Cl

23 2-F, 4-Cl, 5-OCH ₃

24 4-Cl

25 2-F, 4-Cl, 5-OCH ₃

26 2-F, 4-Cl, 5-OCH ₃

27 2-F, 4-Cl, 5-OCH ₃

28 4-Cl

29 2-F, 4-Cl

30 4-Cl

31 2-F, 4-Cl, 5-OCH ₃

32 4-Cl

33 2-F, 4-Cl, 5-OCH ₃

-P-OC ₂ H ₅ CH ₃

C ₆ H ₅ -SO-ii

C ₆ H ₅ CH ₂ CH ₃ OCH ₂ C ₂ H ₅ OOC-CH ₂ CH ₂ CH ₂

CH ₂ S ""

If g Il Il

CH-CH ₃ 0 CH-CH ₃ "

CH ₂ 0 CH ₂ "

Table 1 Compounds of Formula I Example (R ³ Om ^{r2 r3} ( ^β4 ) n

A ¹

X Fp [ ⁰ C]

34 2-F, 4-Cl 5-OCH ₃ H 35 M 4-Cl, Il Il 36 Il Il It Il 37 Il Il

Il

Il

43 3-COOCH (CH ₃ ) COOc ₂ H ₅

4-Cl 5-OCH ₃ "

«Ι

C ₂ H ₅ OOC-CH ₂ NCH ₂ C ₆ H ₅ CH ₂

2,6- (CH ₃ ) ₂ "

-P (OC ₂ H ₅ J ₂

-P (OH) ₂

- ^ -OCH ₃ 0

-SO ₃ H

-S-OCH ₃ C ₆ H ₅ CH ₂ OOC-

C ₂ H ₅ OOC-CH-CH ₃ ""

CH ₂

Il

0 11

Il

Continued Table Example (R)

Compounds of the formula I

A »

fp

52 53 54 55 56 57 58

4-Gl 5-OCH (( 5-0CH- H ITT H 2-F, 4-Cl, It Il 4-Cl 5-OGH ₁ 5-OCH M Il 2-F, 4-Cl, It Il 4-Cl 5-OCH Il Il 4-Cl Il 4-Cl 5-OCH ₃ Il 2-F, 4-Cl, 4-Cl. It 4-Cl It 2-F, 4-Cl, 4-Cl 2-F, 4-Cl, 4-Cl 2-F, 4-Cl, 3-GOOGH ₂ GF ₃

-SO ₂ -CH ₃

-SO ₂ -OCH ₃

^ C ₄ H ₉ OOC-

(CH ₃ ) ₂ i-so ₂ -

ti

C ₂ H ₅ OOC-CO-CH ₃ OOC-

GO ₂ C ₆ H ₅

CH ₂ It GH ₂ Il CH ₂ Il O It oil Il Il ti It 146-148 It It Il Il Il tt tt tt 146-148 Il It ft It It ti It It ti It Il It oil ti Il It Il It tt It tt It Il S It Il Il CH ₂ It Il S CH ₂ It Il S tt It ti CH ^ tt It

Continued Table Example (Rl) m

Compounds of the formula I r2 r3 ( _R 4 _{) n}

A ¹

Fp [ ⁰ C]

60 3-COOCH ₂ CH ₂ OH, 4-Cl H

61 3-COOC ₂ H ₅ , 4-0C ₂ H ₅ "

62 3-COOC ₂ H ₅ , 4-OCF ₂ CHF ₂ "

63 2-F, 4-Cl, 5-OCH ₂ -ChCH "

4-Cl "2-F, 4-Cl, 5-OCH3"

C ₆ H ₅ CH ₂ OOC-

Il

CH ₃

C ₂ H ₅ OOC-CH ₂ -C ₂ H ₅ CH ₂ OOC-

-P (SC ₂ H ₅ ) ₂ C ₆ H ₅ OCH ₂ -CH ₂ CH ₂

SO SO ₂

CH ₂

CH ₂

108-110 143-145

Continuation Table 1 Example

Compounds of the formula I

A ¹

Fp [ ⁰ C]

72 2-F, 4-Cl, 5-OCH3

73 Il 74 Il 75 ti 76 Il 77 Il 78 Il 79 Il 80 ti 81 Il

82

H CO ₂ C ₂ H ₅ CH ₂ CH ₂ CH ₂ 0 01 Il CO ₂ CH ₃ Il Il Il Il 125-128 Il C0 ₂ nC ₈ H ₁₇ It Il ii ti oil CH ₂ OH CO ₂ CH ₃ ti Il It Il 123-126 H CONHn-C ₄ H ₉ Il It Il It 153 CH ₃ CO ₂ C ₆ H ₅ Il Il Il Il 120-122 It CO ₂ CH ₂ C ₆ H ₅ ti Il Il Il oil Il CO ₂ CH ₃ Il Il ti Il Il It CO ₂ C ₂ H ₅ Il ti Il Il Il Il CH-CO ₂ C ₂ H ₅ CH ₃ Il Il Il ti Il F Il CONH-ZwV Cl - Il Il ti Il Il

Continuation Table 1 Example

Compounds of the formula IR ² R ³ (R ⁴ ) _n

A '

Fp [ ⁰ C]

83 2-F, 4-Cl, 5-OCH ₃ H CONHC ₆ H ₅ CH ₂ CH ₂ 84 Il It CO ₂ - ^ - NO ₂ - Il tt 85 2-F, 4-Cl, 5-0CH ₂ CHCH Il CO ₂ CH ₃ Il Il 86 Il ti CO ₂ C ₂ H ₅ Il Il 87 2-F, 4-Cl, 5-OCH ₃ H COCH ₂ Cl CH ₂ CH ₂ 88 Il Il CONHC ₂ H ₅ It Il 89 Il Il CSN (C ₂ H ₅ ) 2 - ti ti 90 Il Il CON (C ₂ H ₅ ) 2 - It ti 91 Il Il C0 ₂ n-C4H9 Il tt 92 ti Il COCH ₂ P (O) (OC ₂ H ₅ ) ₂ - Il Il 93 Il Il CH ₂ CO ₂ C ₂ H ₅ It ti 94 It Il P-OU ^ OC ₂ H ₅ Il Il '

CO-CO ₂ C ₂ H ₅

CH ₂

CH ₂

164-165

Oil

Oil

170-172 oil

Biological examples

Damage to weed plants or crop plant compatibility was scored according to a key in which the effectiveness is expressed by values of 0-5. Where:

0 = no effect or damage

1 = 0-20% effect or damage

2 = 20-40% effect or damage

3 = 40-50% effect or damage

4 = 50-80% effect or damage

5 = 80-100% effect or damage

1. weed effect in the forerun

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were placed in sandy loam soil in plastic pots (0 = 9 cm) and covered with soil. The compounds according to the invention formulated in the form of wettable powders of emulsion concentrates were then used as aqueous suspensions or emulsions with an amount of water applied

of the equivalent 600 l / ha applied in different dosages on the surface of the cover soil.

After the treatment, the pots were placed in the greenhouse and under good growth conditions for the

Weed plants kept (temperature 23 plus / minus 1 ⁰ C, relative humidity 60-80%).

The optical assessment of the plants or emergence damage occurred after emergence of the test plants after a test period of 3-4 weeks in comparison to untreated controls. The results are summarized in Table 2.

2. weed effect postemergence

Seeds or Rhizomstückevon mono- and dicotyledonous weeds were placed in plastic pots (0 = 9 cm) in sandy loam ^v, covered with soil and cultivated in a greenhouse under good growth conditions. Three weeks after sowing, the test plants were treated at the trefoil stage.

The formulated as wettable powders or emulsion concentrates, compounds of the invention were sprayed in various dosages with a water application rate of the equivalent of 600 l / ha onto the green plant parts and (after about 3-4 weeks stand the test plants in the greenhouse under optimal growth conditions, temperature 23 plus / minus 1 ⁰ C, relative humidity 60-80%) scores the effect of the preparations optically in comparison to untreated controls. The results are listed in Table 3.

Table 2: Pre-emergence effect

connection

Example dose

No. kga.i./ha

STM

herbicidal action SIA LOM

ECG

72 2.5 dose Abbreviations: : Stellaria media 5 5 5 SIA LOM CJL 6 2.5 kga.i./ha STM Sinapisalba 5 5 5 5 5 5 73 2.5 2.5 SIA ^: Lolium multiflorum 5 5 5 5 3 5 74 2.5 2.5 LOM = ^: Echinochloacrus galli 5 5 5 2 3 5 75 2.5 2.5 ECG active substance 5 5 5 5 4 5 Table 3: postemergence 2.5 a.i. connection example herbicidal action No. STM ECG 72 5 4 6 3 2 73 3 2 75 5 3

Claims (4)

claims: = independently of one another CH ₂ , S, or one of the two radicals A, A '= CHR ⁴ , C (R ⁴ ) ₂ ,> SO or> SO ₂ ,
= O, S, SO, SO ₂ , CH ₂ CHR ⁴ , C (R ⁴ ) ₂ ,> NR ⁵ ,> NC = X (R ⁵ ) or NC = X (XR ⁵ ), with the proviso that A and B or A 'and B are not simultaneously O, S, SO or SO ₂ allowed,
= OoderS,
= Halogen, NO ₂ , (C ₁ -C ₄ ) AlKyl ₇ -X (C ₁ -C ₄ ) AlKylOdBr (C ₁ -C ₈ ) alkoxyCa ^ OnYl ₁ WObCIdIe last three radicals up to six times by halogen or one or two times may be substituted by OH, (C ₃ -C ₆ ) cycloalkyl, (C ₃ -C ₆ ) -alkenyl, (C ₅ -C ₆ ) -cycloalkenyl, (C ₃ -C ₇ ) -alkynyl, (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ -alkyl) (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkoxycarbonyl, (Cr ^ CsJAlkoxycarabonyl -CsJ-alkoxycarbonyl, (C ₁ -C ₈ ) alkoxyCa rbonylmethylamino, -XH, -X (C 3 -C ₆ ) cycloalkyl, -X (C 3 -C ₆ ) alkenyl, -X (C ₅ -C ₆ ) -cycloalkenyl, -X (C ₃ -C ₇ ) -alkynyl, -X [(C ₁ -C ₄₎ alkoxy- (C ₁ -C ₄₎ alkyl], or-X [(C ₁ -C ₈₎ alkoxycarbonyl], = H, (C ₁ -C ₄₎ -alkyl or (Ci- C ₄ ) hydroxyalkyl,
= H, (C ₁ -C ₆ ) AlKyl, (C ₃ -C ₆ ) CyClOalkyl, (C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ alkoxycarbonylmethyl, phenoxy) C ₁ -C ₄ ) alkyl, nicotinoyl, 1-imidazolylcarbonyl, the meaning of R ⁵ or OO It or -C- a remainder of the formula - Z, wherein the meaning of R ⁵ or the radical OR ⁵ , haloC ^ C ^ alkyl, (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl, phenoxy ^ -CJalkyl, (d-CJAIkylamino or phenylamino, wherein the phenyl radical be substituted by halogen, (C ₁ -C ₄ ) AlkoxyOdBr (C ₁ -C ₄ ) Alkyl can, means also a remainder of the formulas OX ti n -PR ⁷ or -C-CH ₀ -PR ⁷ , R ⁴ = independently of one another the meaning of R ⁵ , -C = X (R ⁵ ) or-C = X (XR ⁵ ), R ⁵ = (Ci-C ₈ ) alkyl, phenyl, pyridyl or benzyl, which are up to three times by (C ₁ -C ₄ ) -alkyl, (C 1 -C ₄ ) alkoxy, halogen, CF ₃ or NO ₂ may be substituted, R ⁶ = independently of one another H, halogen, OH, the meaning of R ⁵ or the radical OR ⁵ , R ⁷ = the meaning of R ⁶ and SH or the radical SR ⁵ , m = 0,1,2,3,4oder5
η = 0,1,2 or 3 mean, as active ingredient (s) and customary formulation auxiliaries included. 2. A herbicidal composition according to claim 1, characterized in that A, A ', B = CH ₂ ; X = O; R ¹ = halogen, (C ₁ -C ₄ ) alkoxy, (C ₃ -C ₇ ) alkynyloxy or (C ₁ -C ₆ -alkoxycarbonyKC-i-CsJ-alkoxycarbonyl, R ² = H, (C ₁ -C ₄ ) alkyl or CH ₂ OH, R ³ = (dC ₄ ) alkoxycarbonyl, (d-CJ alkoxysulphonyl or di (C ₁ -C ₄ ) alkoxyphosphoryl; m = 1,2 or 3 and η = O. 3. Use of compounds of the formula I according to claim 1 or 2, characterized in that they are used as herbicides. 4. A method for controlling undesirable plants, characterized in that applying an effective amount of an agent according to claim 1 or 2 on the cultivated areas to be treated or the plants to be treated.