DD209563A5 - HERBICIDAL AGENT - Google Patents

Abstract

A NEW HERBICIDAL MEANS, WHICH IS SUITABLE, IN PARTICULAR, FOR SELECTIVE SOIL REMEDY IN CEREALS, SOYAS, SUNFLOWER, BEANS AND COTTON PLANTS, CONSTITUTES AS ACTIVE AN ARYLSULFONIMIDE DERIVATIVES OF PHENOXYBENZOESE ACIDS D. GENERAL FORMULA (I). IT IS ADVISABLY USED IN A COST OF EXPENSION OF 0.1 TO 2 KG OF ACTIVE SUBSTANCE. A HERBICIDIC EFFECTIVE COMPOUND CAN BE MADE BY REPLACING A PHENOXY-N-ALKYLSULFONYLBENZAMIDE COMPOUND D. GENERAL FORMULA (II) WITH A HALOGENING AGENT AND THE GENE FORMULA IMDOYLHALOGENIDE (III) OBTAINED WITH A HIGH 2-H COMPOUND TO THE CONCENTRATED CONNECTION OF THE GENERAL FORMULA (I) TO BE IMPLEMENTED.

Description

The invention relates to a herbicidal composition containing as active ingredient an arylsulfonimide derivative of a phenoxybenzoic acid.

Characteristic of the known technical solutions:

Also known are the acifluorfen designated 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitrobenzoic acid and its salts and the herbicidal activity of these compounds.

In particular, it has been recommended to apply these compounds to soybean crops after emergence of the crops in order to eradicate weeds, especially the dicotyledonous weeds. In such an application, a herbicide must have the following properties at the dose considered:

- it must be the main weeds or certain

eliminate selected weeds and - it must be selective to soy.

Attempts have been made to improve the herbicidal properties of acifluorfen and its salts and numerous

Derivatives of these compounds developed or prepared, especially alkyl, cycloalkyl, thioalkyl and Phcnylester and mono- or dialkylated amides. Dedicated compounds are described in U.S. Patents 3,652,645, 3,784,635, 3,873,302, 3,983,168, 3,907,866, 3,798,276, 3,928,416, and 4,063,929. EP Pat. Nos. 3,416 and 2,3392 disclose sulfonamide derivatives of phenoxybenzoic acids.

Object of the invention: 10

An object of the invention is to provide a new herbicidal composition having a better combination of heribidal properties in terms of efficacy against weeds and crop selectivity. Another object of the invention is to provide a herbicidal composition which has a better selectivity for crops other than soybean, in particular for cereals.

Presentation of the Invention:

The invention relates to a herbicidal composition which, in addition to a conventional inert carrier as the active ingredient, a compound of general formula 25th

R ² '= N-S0 ₂ -R ¹

(D

contains

in which W, Y, Y ¹ , X, Z ¹ and Z are each a hydrogen or a halogen atom or an NO-- or CN- group or a polyhaloalkyl group, such as CF 1 - or an alkyl or alkoxy group, where the different alkyl or alkoxy groups usually have 1 to 4 carbon atoms,

R is an alkyl, alkenyl, alkynyl or phenyl group

which is optionally substituted,

2 3

R is a halogen atom or one of the groups CN, SCN, OR,

SR ⁴ or NR ⁵ R ⁶ means

R is an optionally substituted alkyl group or an allyl, propargyl, alkylcarbonyl, alkylidene

imino group or represents the succinimido group,

4 R is hydrogen or a cation or one of the

has meanings given for R,

R is a hydrogen atom or an optionally substituted alkyl group or an alkylcarbonyl or alkylsulfonyl group,

R has one of the meanings given for R or is a cation or the group CN or the group OR, where R stands for a hydrogen atom or for a cation or for an alkyl group, a carboxylic acid ester group or a carboxamido group or an alkylcarbonyl group.

Preferably, these substituents are usually so

20 chosen that

W is a hydrogen or a halogen atom, in particular Cl, Br or F or the NO ~ or CN group, Y is a hydrogen or halogen atom, in particular Cl, Br or F or one of the groups NO_, CN, CF- or CH ₃ , Y ¹ , Z ¹ and Z are each a hydrogen or a halogen atom, in particular Cl, Br or F, X is a halogen atom, in particular Cl, Br or F or one of the groups ΝΟ_, CF-, CH- or CH ₅ , R is an alkyl group having usually 1 to 12 carbon atoms, and preferably 1 to 6 carbon atoms, optionally with

one or more halogen atoms, in particular Cl, Br or F, or by one or more alkoxy or alkylthio groups

usually 1 to 4 carbon atoms or with one or more groups CN or with

a phenyl group is substituted, which in turn is optionally substituted, especially with one or more halogen atoms or

an alkenyl or alkynyl group having usually 2 to 4 carbon atoms, in particular the vinyl, ethynyl, allyl or propargyl group or

a phenyl group, which in turn may be substituted, especially with one or more halogen atoms or with nitro groups or with alkyl groups, which usually have 1 to 4 carbon atoms;

2 R is a halogen atom, preferably chlorine or one of

Groups CN, SCN, OR ³ or SR or NR ⁵ R ⁶ ;

R is an alkyl group which usually has 1 to 4 carbon atoms and is optionally substituted by: one or more halogen atoms, in particular Cl, Br or F or with one or more alkoxy or alkylthio groups, which usually have 1 to 4 carbon atoms or with a or more N0 ~ - or CN groups or with a carboxylic acid group or one of its derivatives of the salt, ester or amide type, in particular a group COOR, where R is a hydrogen atom or an alkyl group having usually 1 to 4 carbon atoms or a metal cation or the ammonium cation or with an alkylcarbonyl group, in particular the acetyl group or with a phenyl group, which in turn may be substituted, especially with one or more halogen atoms or with a group

in which R ⁸ and R ^{9 may be} identical or different and each represents a hydrogen atom or an alkyl group having usually 1 to 4 carbon atoms or R is an allyl or propargyl group or an alkylcarbonyl group, in particular the acetyl group or a group

R ⁸

-N = Cr or -N ίο \ 9

8 9 wherein R and R have the meaning given above;

4 R is a hydrogen atom or an alkali cation or the ammonium cation or has one of the meanings given for R,

R is a hydrogen atom or an alkyl group having usually 1 to 4 carbon atoms, which is optionally substituted by a carboxylic acid group or its derivatives of the salt, ester or amide type, especially by a group COOR, wherein R has one of the meanings already indicated or

an alkylcarbonyl or alkylsulfonyl group, especially the acetyl group or methanesulfonyl group; 5 R has one of the meanings given for R or an alkali metal cation or the ammonium cation or the group CN or a group OR, wherein R has one of the following meanings: hydrogen atom or

30 an alkali cation or the ammonium cation or

an alkyl group having usually 1 to 4 carbon atoms, optionally with a carboxylic acid group or one of its derivatives of the salt, ester or amide type, in particular

7 7

a group COOR is substituted, in the R one of the

35 already given above meanings or

a group COOR or CONHR, where R is one of the above

has specified meanings or

an alkylcarbonyl group, especially the acetyl group.

A preferred subgroup of the active ingredients provided by the invention consists of those compounds of formula (1) in which W is NO ₂ , У is Cl, У and Z ^{1 are} each a hydrogen atom, X is a chlorine atom or the CF., - group and Z is a chlorine or fluorine atom or preferably a hydrogen atom. Furthermore are

2 the compounds of particular interest in which R represents a chlorine atom or an alkoxy group and the compounds in which R and R each represent an alkyl group

4, while R represents a hydrogen atom or an alkyl group and R represents a hydrogen atom or the methanesulfonyl group, and R represents a hydrogen atom or an alkali cation or the ammonium cation. The inventively provided as active compounds of the above formula (I) can occur in two diastereoisomeric forms E and Z, which are in thermodynamic ami apparent equilibrium with each other, according to the following scheme

.-R

Z ¹ Z

In addition, certain compounds may have tautomeric forms, in particular the compounds in

4, each of R 5 and R 4 represents a hydrogen atom, as shown by the following schemes:

С - NH-SO ₂ -R ¹

ζ · ζ

These diastereoisomeric and tautomeric forms are also used as active ingredients, as are the physically distinct forms resulting, for example, from differences in conformation or intramolecular or intermolecular hydrogen bonds or other analogous phenomena.

The compounds of the invention intended as active compounds are prepared as follows: a compound of the general formula (II)

-У \ -о-

CO-NK-SO ₂ -

(ID

Z'Z

is reacted with a halogenating agent in such a way that an imidoyl halide of the general formula (III)

shark

= N-

(III)

in which hai is a halogen atom, preferably the chlorine atom.

As the halogenating agent, mention may be made of COCl ₂ , SO-Cl ₂ , (COCl) ₂ , PCl ₅ , PCl ₃ , POCl ₃ , SOCl ₂ and others, with COCl ₂ and PCl _{5 being} preferred. The reaction is advantageously carried out between -30 and +150 ⁰ C in a solvent, preferably in an aliphatic or aromatic, optionally halogenated hydrocarbon, such as dichloromethane, 1,2-dichloroethane, toluene or chlorobenzene. The reaction is carried out in the presence or absence of an acid acceptor, such as a tertiary amine, for example triethylamine or pyridine.

The imidoyl halide of the general formula (III) is then reacted with a compound of the general formula (IV)

R ² -H

(IV)

implemented, in which R has the meaning given above, with the exception of halogen, followed by obtaining the desired compound of the general formula (I). The reaction is usually carried out at 0 to 150 ⁰ C in an inert solvent and in the presence of an acid acceptor, such as a tertiary amine, for example triethylamine or

15

9 -

Pyridine. Suitable solvents are the aliphatic or aromatic, optionally halogenated hydrocarbons, such as dichloromethane, 1,2-dichloroethane, toluene or the ethers or nitriles.

2 3

In the cases where R is OR, certain compounds of the general formula (I) can also be prepared according to the following reaction:

_γ ι γ

shark

= N-SO ₂ -R '

+ OM

20 25 30

In this reaction scheme, M represents a hydrogen atom or an alkali metal atom, such as the sodium or potassium atom.

This latter reaction is advantageously carried out between 10 and 150 ⁰ C. It is also possible to work in a solvent which consists of a compound of the formula R ³ OH.

If R is SR or NR R, certain compounds of the general formula (I) can also be prepared according to the above reaction scheme, but with a reaction partner of the formula R -SM or R R -NM instead of R -OM.

be presented.

These latter two reactions are advantageously carried out between 10 and 150 ^° C., in an inert solvent, such as an aliphatic or aromatic, optionally halogenated hydrocarbon, such as toluene, xylene or chlorobenzene.

When R is OR, certain compounds of general formula (I) can also be prepared by reacting a compound of general formula (VI)

R ⁵ -N-OH

X Ж Ж MM X Ж

(VI)

with a compound of general formula (VII)

R ¹⁰ -hal (VII)

where hai is a halogen atom. The reaction is usually carried out between 0 and 150 ^° C. in an inert solvent and in the presence of an acid acceptor, such as a tertiary amine or an alkali metal hydroxide, preferably NaOH or KOH. If a tertiary amine is used as acid acceptor, suitable solvents are the aliphatic or aromatic, optionally halogenated hydrocarbons or ethers or nitriles. If an alkali metal hydroxide is used as the acid acceptor, the aliphatic alcohols, such as methanol, ethanol, ethylene glycol,

4 optionally with the addition of water in question. If R or R or R is an alkali cation or the ammonium

cation, certain salts of the compounds of the general formula (I) can be prepared by processes known per se, for example by adding alkali metal hydroxides or alkali metal alkoxides in a solvent medium, usually simply at room temperature.

The production of individual compounds of general formula (I) suitable as active substance is described below.

The compounds 1 to 30 prepared are summarized in Table 1. They were identified by their NMR spectrum, their IR spectrum and by mass spectroscopy. The various analytical methods further showed that under the analytical conditions, the compounds were able to react either in their two diastereomeric forms.

4 men E and Z templates, or if one of the groups R or R had the meaning of hydrogen atom, in the two tautomeric Formdn, in each case in equivalent or in different proportions.

Connection 1

_a ) In 100 ml of toluene, 22 g (0.05 mol) of 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonyl-benzamide and 10.4 g (0.05 mol) of PCl ₅ suspended.

The suspension was heated with stirring and refluxed until HCl evolution ceased (about 1/2 hour). Toluene and POCl were withdrawn; 22.8 g of a yellow viscous oil remained, which was purified by chromatography on silica with toluene as the eluent. This gave 18.5 g, corresponding to a yield of 81%, 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonyl-benzimidoyl chloride as a white solid, which melted at 83 ° C and the following formula

CF.

N-SO ₂ CH

(Compound 1)

The structural formula of this compound was determined by NMR

Spectrum and IR spectrum confirmed: IR absorption band at 1650 cm ^-1 (C = N).

Mass spectrometry was used to observe fragments of masses 410, 437 and 326.

b) In 400 ml of toluene, 43.9 g (0.1 mol) of 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonylbenzamide were suspended.

It was stirred, then slowly at room temperature 15.1 g (0.15 mol) of triethylamine were added. Then the reaction mixture was cooled to -10 ⁰ C and kept at this temperature while slowly bubbled by 11.9 g (0.12 mol) of COCl- were passed. Stirring was continued at -10 ⁰ C until the COj-evolution had ceased (about 1 hour). The precipitated triethylamine chlorohydrate was filtered off and washed with toluene. The filtrates were combined and the toluene evaporated. 43.7 g (yield 96%) of compound no. 1 were obtained.

Connection 2

a) A solution of 30 g (0.066 mol) of compound 1 and 70 ml of methanol was prepared. The solution was stirred; Then, slowly at room temperature, a solution of 3.6 g (0.066 mol) of sodium methylate in 30 ml of methanol was added and stirred for a further hour at room temperature. The precipitated NaCl was filtered off and the methanol was stripped off. The residual oil was purified by chromatography on silica gel with dichloromethane as eluent.

This gave 13 g (yield 44%) of methyl 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonyl-benzimidate in the form of a white solid, which melted at 126 ° C and corresponded to the formula :

NO (compound 2)

b) A solution of 95.4 g (0.21 mol) of compound 1 and 200 ml of methanol was prepared. The solution was stirred and then heated to reflux until HCl evolution ceased (about 1/2 hour). It was cooled to 5 ° C, the precipitate was filtered off, washed with water and recrystallized from methanol. This gave 61.9 g (yield 65%) of compound 2.

10 compounds 3 to 8

The compounds 3 to 8 shown in Table 1 were prepared in an analogous manner as compound 2.

15 compounds 9 to 14

A solution of 0.01 mol of compound of the formula R OH, 1.4 ml of triethylamine and 10 ml of ethyl ether was prepared. The solution was stirred, cooled to 5 ° C and treated dropwise with a solution of 4.6 g of compound 1 in 20 ml of ether. Then it was stirred for a further 4 hours at room temperature. The precipitated Triethylaminchlorhydrat was filtered off and washed with ether, dried over sodium sulfate and concentrated.

5 The residual oil was purified by chromatography on silica using dichloromethane as eluent.

Compounds 15 to 18

A solution of 0.01 mol of compound of the formula R OH, 1.4 ml of triethylamine and 10 ml of toluene was prepared. The solution was stirred; then a solution of 4.6 g of compound 1 in 20 ml of toluene was added gradually at room temperature.

The reaction mixture was heated to 90 ^° C. and kept at this temperature for a further 3 hours. The precipitated triethylamine chlorohydrate was filtered off and washed with toluene. The filtrates were combined, washed with water, dried over sodium sulfate and concentrated. The residual oil was purified by chromatography on silica using dichloromethane as eluent.

Compounds 19 to 21 10

Compounds 19 to 21 were prepared similarly to compounds 9 to 14, by reacting the compound of the general formula R OH with a compound of the general formula

4 my formula R SH has been replaced. Compound 20 was prepared by reacting compound 19, 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonylthiobenzamide, with a stoichiometric amount of aqueous sodium hydroxide solution (or sodium methoxide in methanol) followed by isolation Evaporation of the water (or methanol) synthesized in a conventional manner.

Compounds 22 and 23

The two compounds 22 and 23 were prepared according to compounds 15 to 18, by

4 bond of the general formula R SH has been replaced.

Connections 24 to 27

The compounds 24 to 27 were prepared analogously to the compounds 9 to 14, by replacing the compound of the general formula R OH by a compound of the general formula R R NH.

Connection 28

A solution of 3 g (0.0066 mol) of Compound 27, 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonyl-N'-hydroxybenzamidine, 20 ml of ethanol and 5 ml of water manufactured. The whole thing was touched; then, at room temperature, 1.1 g (0.0066 mol) of methyl 2-bromopropionate and 0.26 g (0.0066 mol) of NaOH were added. The mixture was refluxed for 2 hours. Ethanol and water were then removed and the residue taken up in dichloromethane. The organic phase was washed with water, dried over sodium sulfate and concentrated. The residual oil was purified by chromatography on silica using a 97: 3 mixture of dichloromethane and methanol as eluent. This gave 1.2 g (yield 34%) of 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonyl-N '- (1-carbomethoxy) ethoxybenzamidine as a viscous mass having the formula

NH-O-CH (CH ₃ ) - COOCH ₃

C = N-SO ₂ -CH ₃

(Compound 28)

corresponded.

successively

Compounds 29 and 30

A suspension of 1.3 g (0.01 mol) of potassium salt of the methanesulfonamide in 30 ml of toluene was prepared. The mixture was stirred; then it was at room temperature

a solution of 4.6 g (0.01 mol) of compound 1 in 20 ml of toluene was added. The whole was refluxed for 4 hours. Then the precipitated KCl was filtered. The organic filtrate was washed with water, dried over sodium sulfate and concentrated. The residual oil was purified by chromatography on silica using a 90:10 mixture of dichloromethane and methanol as eluent. This gave 1.5 g (yield 29%) of 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N, N ¹ -bis-methanesulfonylbenzamidine as a white solid, which melted at 211 ° C and following formula:

NH - SO ₉ --CH, C = N - SO ₂ --CH ₃

(Compound 29)

Compound 30 was prepared by reacting at room temperature the compound just obtained with a stoichiometric amount of aqueous sodium hydroxide solution (or sodium methoxide in methanol) and then removing the water or methanol in a manner known per se

The compounds 1 to 30 can be represented by the following formula:

С = N-SO ₂ - R

1 2

The meaning of the substituents R and R for the various compounds and the yields and melting points of the compounds obtained are summarized in Table (1).

In the compound ig, the second tautomeric form of the formula predominates:

It

NH-SO ₂ -CH ₃

The compounds 15, 16, 23 and 28 containing an asymmetric carbon atom exist in the two enantiomeric forms R or S. In this case, the general formula (I) represents one or the other of these two forms or represents the mixture both forms in either equivalent ratios (racemate) or in a ratio in which one or the other form outweighs.

connection

In 50 ml of toluene were suspended 7.4 g (0.018 mol) of 5- (2 ', 4'-dichlorophenoxy) -2-nitro-N-methanesulfonylbenzamide and 3.8 g (0.018 mol) of PC1_. The whole thing was

and heated to reflux until HCl evolution ceased (about 1/2 hour). Toluene and ^P ° C1 ₃ were withdrawn. There remained 7.7 g of a viscous brown oil which was dissolved in 25 ml of methanol. This methanolic solution was stirred and then heated to reflux until HCl evolution ceased (about 1/2 hour). It was cooled to 5 ° C and the resulting precipitate was filtered off and then recrystallized from methanol. This gave 4.6 g (yield 60%) of methyl 5- (2 ', 4'-dichlorophenoxy) -2-nitro-N-methanesulfonylbenzimidat in the form of a white solid, which melted at 163 ° C and the following formula:

0 - CH,

1 ³

C = N-SO ₂ -CH-

In an analogous manner, the following compounds could be prepared:

Methyl-5- (2'-chloro-4'-trifluoromethylphenoxy) -2-chloro-N-methanesulfonyl-benzimidate

Methyl 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-bromo-N-methanesulphonylbenzimidate Methyl 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-cyano-N-methanesulphonylbenzimidate

Methyl-5- (2 ', 4'-dichlorophenoxy) -2-chloro-N-methansulfonylbenzimidat

Methyl-5- (2 x, 4'-dichlorophenoxy) -2-bromo-N-methansulfonylbenzimidat

Methyl-5- (2 ', 4'-dichlorophenoxy) -2-cyano-N-methansulfonylbenzimidat

Methyl 5- (2 *, 6'-dichloro-4'-trifluoromethylphenoxy) -2-chloro-N-methanesulfonylbenzimidate Methyl 5- (2'-bromo-4'-trifluoromethylphenoxy) -2-nitro-N- methansuIfonyl-benzimidate

Methyl 5- (2'-iodo-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonylbenzimidate Methyl 5- {2'-nitro-4'-trifluoromethylphenoxy) -2-nitro-N-

10 methanesulfonyl benzimidate

Methyl-5- (2'-cyano-4'-trifluoromethylphenoxy) -2-nitro-N-methansuIfonyl-benzimidate

Methyl 5- (bis-2 ', 4'-trifluoromethylphenoxy) -2-nitro-N-methansuIfonyl-benzimidate

Methyl 5- (2 ', 6'-dichloro-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonylbenzimidate Methyl 5- (2'-chloro-6'-fluoro-4'-trifluoromethylphenoxy) -2 nitro-N-methanesulfonyl-benzimidate methyl-5- (2 *, 3 ', 6'-trichloro-4'-trifluoromethylphenoxy) -

20 2-nitro-N-methanesulfonyl-benzimidate

Methyl 5- (2'-nitro-6'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-methanesulfonyl-benzimidate Methyl-5- (2 ', 3', 5 ', O'-tetrafluoro-4 '-trifluoromethylphenoxy) -2-nitro-N-methanesulfonylbenzimidate Methyl 5- (2'-trifluoromethyl-4'-chlorophenoxy) -2-nitro-N-methanesulfonylbenzimidate

Methyl 5- (2'-methyl-4'-chlorophenoxy) -2-nitro-N-methanesulfonylbenzimidate Methyl 5- (2'-nitro-4'-chlorophenoxy) -2-nitro-N-methane

30 sulfonyl benzimidate

Methyl 5- (2 ', 4', 6'-trichlorophenoxy) -2-nitro-N-methanesulfonylbenzimidate

Methyl 5- (2 ', 4'-dichloro-6'-fluorophenoxy) -2-nitro-N-methanesulfonyl benzimidate

Methyl-5- (2 ', 3', 4'-trichlorophenoxy) -2-nitro-roethansulfonyl-benzimidate

Methyl-5- (2 ', 4 ^1, 5'-trichlorophenoxy) -2-nitro-N-methanesulfonyl-benzimidate

Methyl 5- (2 ', 3 ¹ , 4 * , 6' -tetrachlorophenoxy) -2-nitro-N-methanesulfonyl benzimidate

Methyl 5- (2'-chloro-4'-bromophenoxy) -2-nitro-N-methanesulfonylbenzimidate Methyl 5- (2 ', 4'-dibromophenoxy) -2-nitro-N-methanesulfonyl

10 benzimidate

Methyl 5- (2 ', 4', 6 '-tribromophenoxy) -2-nitro-N-methanesulfonyl-benzimidate

Methyl 5- (2'-chloro-4'-fluorophenoxy) -2-nitro-N-methanesulfonyl benzimidate

Methyl 5- (2'-chloro-4'-methylphenoxy) -2-nitro-N-methanesulfonylbenzimidate

Methyl 5- (2'-nitro-4'-methylphenoxy) -2-nitro-N-methanesulfonylbenzimidate Methyl 5- (2 ', 3', 6'-trichloro-4'-methylphenoxy) -2- nitro-N-

20 methanesulfonyl benzimidate

Methyl 5- (2'-chloro-4'-ethylphenoxy) -2-nitro-N-methanesulfonylbenzimidate

Methyl 5- (2 ', 6'-dichloro-4'-ethylphenoxy) -2-nitro-N-methanesulfonylbenzimidate

5-Methyl-5- (2 ', 3', 5 ', 6'-tetrafluoro-4'-ethylphenoxy) -2-nitro-N-methanesulfonyl-benzimidate Methyl 5- (3', 5'-dichlorophenoxy) -2 nitro-N-methanesulphonylbenzimidate methyl-5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-

30 N-n-propanesulfonyl-benzimidate

Methyl-5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-trifluoromethanesulfonyl-benzimidate

Methyl 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-vinylsulfonylbenzimidate

Methyl 5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-ethynylsulfonylbenzimidate

Methyl-5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-a1IyIsuIfonyl-benzimidate

Meth yl-5- (2'-chloro-4'-trifluoromethylphenoxy) -2-nitro-N-propargylsulfonyl benzimidate

The herbicidal compositions according to the invention contain a compound of the general formula (I) in combination with agriculturally acceptable solid or liquid carriers and surface-active agents. In particular, the inert and customary carriers and the conventional surfactants are suitable.

The agents may also contain any other components, such as protective colloids, adhesives, thickeners, thixotropic agents, penetrants, stabilizers, scavengers and a.m. and other known active ingredients with pesticidal properties, especially insecticides, fungicides and herbicides or with properties that promote the growth of plants, especially fertilizers or plant growth regulating properties. In general, the compounds provided according to the invention can be combined with all solid and liquid additives which are customary for the production of pesticides.

The application doses or application rates for the active substances provided according to the invention can vary within wide limits and, above all, depend on which weeds are involved and to what extent the plantings of the crop plants are usually affected.

In general, the herbicidal compositions contain 0.05 to 95% by weight of one or more of the active compounds according to the invention, 1 to 95% by weight of one or more solid or liquid carriers and optionally 0.1 to about 20% by weight. % of one or more surfactants.

As the carrier in the present description organic and inorganic substances of natural or synthetic origin are referred to, with which the active ingredient is combined to facilitate its application to the plant, on the seed or on the ground. This carrier is thus generally inert and must be agriculturally compatible, especially compatible for the treated plant. The carrier may be a solid such as clays, natural or synthetic silicates, silicic acid, resins, waxes, solid fertilizers and the like; or it is liquid such as water, alcohols, in particular butanol, esters, in particular methyl glycol acetate, ketones, in particular cyclohexanone and isophorone, petroleum fractions, aromatic hydrocarbons, in particular the xylenes or paraffinic hydrocarbons, aliphatic chlorinated hydrocarbons, especially trichloroethane or aromatic chlorinated hydrocarbons, in particular the chlorobenzenes, water-soluble or with water

20 miscible solvents such as dimethylformamide,

Dimethylsulfoxide, N-methylpyrrolidone, liquefied gases, and the like.

The surfactant may be an emulsifier, a dispersant or wetting agent, and ionic or nonionic, or a mixture of such agents. Examples thereof are the salts of polyacrylic acids, the salts of lignosulfonic acids, salts of phenolsulfonic acids or naphthalenesulfonic acids, polycondensation products of ethylene oxide and fatty alcohols or fatty acids or fatty amines, substituted phenols, especially alkylphenols or

Arylphenols, salts of sulfosuccinic acid esters, taurine derivatives, especially alkyl taurates, esters of phosphoric acid and alcohols or polyoxyethylated phenols, esters of fatty acids and polyols and the derivatives of the above compounds with sulfate, sulfonate and phosphate groups. The presence of at least one surfactant is generally necessary when the active ingredient and / or the inert carrier are not water-soluble and the vehicle for the application is water.

The herbicidal compositions of the invention may be solid or liquid.

Examples of solid compositions are powders for dusts containing up to 100% of the compound of the formula (I) of my invention and granules, in particular those obtained by extrusion, by compression, by impregnation of a granulated material

20 carriers or obtained by granulation from a powder; the content of the compound of the general formula (I) in these granules is 0.5 to 80% in the latter cases. The fixed funds usually contain

25 20 to 80% active ingredient.

Examples of liquid agents, i. Agents which are liquid in use are solutions, in particular emulsifiable concentrates, emulsions, concentrated suspensions, aerosols, wettable powders or wettable powders, self-dispersible granules and pastes.

The emulsifiable or soluble concentrates usually contain 10 to 80% active ingredient; the ready emulsions or solutions in turn ent hold 0.01 to 20% active ingredient. In addition to the solvent, the emulsifiable concentrates may contain 2 to 20%, if necessary, suitable additives 1U, for example stabilizers, surfactants, penetrants, corrosion inhibitors, dyes and adhesives.

Starting from these concentrates, emulsions or solutions of any desired concentration, which are particularly suitable for application to the plants, can be prepared by dilution with water.

The concentrated suspensions which can be sprayed are prepared so as to obtain a stable flowable product in which the individual components do not settle (fine grinding); they usually contain 10 to 75% active ingredient, 0.5 to 15% surfactants, 0.1 to 10% thixotropic agents, 0 to 10% further additives such as anti-foaming agents, corrosion inhibitors, stabilizers, penetrants and adhesives and as a carrier water or an organic Liquid in which the active substance is little or insoluble. Certain solid organic substances or inorganic salts may be dissolved in the carrier to additionally counteract sedimentation or as antifreeze for the water.

The wettable powders or wettable powders are usually prepared so that they contain 20 to 95% active ingredient and in addition to the solid support 0 to 5% of a wetting agent, 3 to 10% of a dispersant and if necessary 0 to 10% of one or more stabilizers and / or or other additives such as penetrants, adhesives or anticaking agents, dyes and the like

10 For the production of these wettable powders or wettable

Powder, the active ingredients in corresponding mixers are intimately mixed with the further additives or the porous carrier is impregnated with the molten agent and the whole is ground in mills or other suitable reduction means. In this way, spray powders are obtained which can advantageously be wetted and brought into suspension. They can be suspended in water at any desired concentration; These suspensions are particularly well suited for application to the foliage of the plants.

The "self-dispersible" granules (English term "dry flowable" - there are 25 slightly water-dispersible granules) have

a composition substantially equal to that of wettable powders. You can by granulating the described for wettable powders

Batches are prepared or by wet route, i. by contacting the finely divided active substance with the inert carrier or filler and with a little water, for example 1 to 20%, or by contacting the finely divided active substance with the aqueous solution of the dispersant or binder and then drying and sieving, or even on dry Routes by means of compression and subsequent crushing or grinding and sieving.

Pastes can also be made instead of wettable powders. The conditions and modalities of preparation and use of these pastes are the same or comparable to those of wettable powders or wettable powders.

As already stated, the aqueous dispersions and emulsions, for example the agents obtained by diluting a wettable powder or an emulsifiable concentrate with water, belong to the applicable agents provided according to the invention. The emulsions may be water-in-oil or oil-in-water emulsions and have a thick mayonnaise-like consistency.

All these aqueous dispersions or emulsions or spray mixtures can be applied to the cultures or

Use plantings to be weed-cleared by any suitable means, generally by spraying or spraying, in dosages generally of the order of 100 to 1200 sprayings per hectare.

The granules used for soil treatment are generally prepared so that their dimensions are 0.1 to 2 mm; they can be made by agglomeration or impregnation. Preferably, the granules contain 1 to 25% active ingredient and 0 to 10% additives such as stabilizers, release retarders, binders and solvents.

The compositions according to the invention are used for weed killing in crops, especially in cereal crops such as wheat, barley and maize as well as in soya, sunflowers, cotton and beans. For this purpose, an effective and non-phytotoxic amount of at least one of the compounds according to the invention is applied to the plants and / or to the soil of the area which is to be freed from weeds. These compounds are used in practice in the form of the herbicidal compositions of the invention described above. In general, amounts of active ingredient of 0.01 to 5 kg / ha, preferably from 0.1 to 2 kg / ha lead to good results, of course, the choice of the amount of active substance to be applied, of the problem to be solved by the climatic conditions

and the crops considered. The treatment can be done either before emergence of the crops and the weeds or before sowing the crops incorporating into the soil - this incorporation is thus an additional measure in the inventively provided treatment, or after emergence - done. Other types of treatment are also possible: for example, one can apply the active ingredient to the soil with or without incorporation, and prior to planting the crop planting.

The agents according to the invention can be used to treat annual crops as well as perennial crops. In the latter case, the agents are preferably localized, for example applied in the rows between the crops.

2 0 Example 1:

Composition of emulsifiable concentrates:

a) Active ingredient 250 g of polyethoxylated alkylphenol 3U g

25 calcium alkylarylsulfonate 50 g

Petroleum fraction which passes at 160 to 185 ⁰ C 670 g

b) Active ingredient 350 g 30 polyethoxylated castor oil 60 g

Sodium alkylarylsulfonate 40 g

Cyclohexanone 150 g

Xylene 4 00 g

c) Active ingredient 400 g of polyethoxylated alkylphenol 100 g of ethylene glycol methyl ether 250 g of aromatic petroleum fraction, at

160 to 185 ° C passes 250 g

d) Active ingredient 400 g of polyethoxylated tristyrolphenol phosphate 50 g

polyethoxylated alkylphenol

Phosphate 65 g

Sodium alkylbenzenesulfonate 35 g

Cyclohexanone 300 g

aromatic petroleum fraction, with

Mp 160-185 ° C 150 g

e) Active ingredient 400 g / l Alkalidodecylbenzolsulfonat 24 g / l oxyethylated nonylphenol with

10 ethylene oxide units 16 g / l 20 cyclohexanone 200 g / l aromatic solvent made up to 1 liter

f) Active ingredient 250 g epoxidized vegetable oil 25 g

Mixture of alkylarylsulfonate and

Polyglycol fatty alcohol ether 100 g

Dimethylformamide 50 g

Xylene 575 g

- 32 -

Example 2

Suspension concentrate: 500 G active substance polyethoxylated tristyrylphenol 50 G phosphate 50 G polyethoxylated alkylphenol 20 G sodium polycarboxylate 50 G ethylene glycol Organopolysiloxane oil (antifoam 1 G medium) 1 / 5g polysaccharide 316 / 5g water Example 3

Networkable powders:

a) active ingredient 50%

Calcium lignosulphonate, deflocculant 5% isopropylnaphthalenesulphonate, anionic wetting agent 1% silica to prevent

clumping 5% Kaolin, filler 39% b) active ingredient 80% Natriumalkylnaphtalinsulfonat 2% sodium lignosulfonate 2% Silica to prevent the Kiumpenbildung 3% kaolin 13% c) active ingredient 50% Natriumalkylnaphtalinsulfonat 2% Methyl cellulose low Viskosi ty 2% diatomaceous earth 46%

d) active ingredient 90%

Sodium dioctyl sulfosuccinate 0.2%

synthetic silica 9.8%

e) Active ingredient 400 g

Sodium lignosulfonate 50 g

Sodium dibutyinaphthalenesulfonate 10 g

Silica 540 g

f) active ingredient 250 g isooctylphenoxy-polyoxyethylene

Ethanol 25 g mixture of equal parts by weight of chalk from Champagne and hydroxy

ethylcellulose 17 g

Sodium aluminum silicate 543 g

Diatomaceous earth 165 g

g) active substance 100 g mixture of sodium salts of

saturated fatty acid sulfates 30 g condensation product of naphthalene

sulfonic acid and formaldehyde 50 g

Kaolin 820 g

5 Example 4

Self-dispersible granules: Active ingredient 800 g

Sodium alkylnaphthalenesulfonate 20 g

Sodium methylene-bis-naphthalene sulfonate 80 g

Kaolin 1U0 g

Example 5

Granules:

Active ingredient 50 g

Propylene glycol 25 g

cooked linseed oil 50 g

Application example 1

Preemergence of plants.

in 9 χ 9 χ 9 cm pots filled with light field soil a number of seeds were sown, the number of which was based on the type of plant considered and on the thickness of the seed

 10

The pots were treated with a spray mixture in an amount corresponding to an application rate (volume) of 500 l / ha containing the active ingredient in the

contained desired concentration.

The treatment with the spray mixture was thus carried out as long as the seeds were not yet covered with soil (spray mixture here generally means the diluted with water means, as applied to the plants).

The spray mixture used for the treatment was an aqueous suspension of the active ingredient containing 0.1 wt .-% surfactant consisting of a polyethoxylated alkylphenol, in particular polyoxyethylated nonylphenol (trade name Cemulsol NPlO) and 0.04 wt .-% surfactant, consisting of a Polyoxyethylene sorbitoleate (Tween 20).

This suspension was obtained by mixing the components together and grinding to a mean particle size below 40μΐη. Depending on the active ingredient concentration of the spray mixture, the applied dose was

35 active ingredient 0.25 to 4 kg / ha.

After treatment, the seeds were covered with a layer of soil about 3 mm thick.

The pots were then placed in pans, 5 in which they were watered from below and held for 21 days at room temperature and at 70% relative humidity.

After 21 days, the number of live plants was counted 10 in each pot and treated with

compared to the number of live plants present in a pot treated for comparison under the same conditions but with no active ingredient spray. In this way the percentage of eradication of the treated plants relative to untreated plants was determined. A percent kill of 100% means that the plant species in question had been completely destroyed, and a percent kill of 0% means that the number of live plants in the pot treated was equal to the number of plants treated as control

serving pot

 25

Application Example 2 Post-emergence treatment of plants.

In 9 χ 9 χ 9 cm pots filled with light field soil, seeds were sown, the number of which varied according to the type of plant considered and the thickness of the plant

Seed grain straightened

 35

Subsequently, the grains were covered with a layer of soil about 3 times thick and allowed to germinate until the plantlets had reached the desired stage of development. The stage of growth sought for the treatment of grass plants (monocotyledonous plants) was the stage of the "second leaf in formation". The appropriate stage for soy was the "first three-leaved spread leaf" stage. The stage of treatment for the other dicotyledonous plants was the stage "spreading cotyledons, first real leaf in development".

The pots were then sprayed with the spray mixture in an amount corresponding to an application rate (volume) of 500 l / ha and containing the active ingredient in the desired concentration.

The spray mixture was prepared in the same manner as in Example 32.

Depending on the active ingredient concentration of the slurry, the applied active ingredient dose was 0.125 to 4 kg / ha.

The treated pots were then placed in vats in which they were watered from below and kept at room temperature and 70% relative humidity for 21 days.

After 21 days, the number of live plants in each pot treated with the spray mixture containing the active ingredient was counted and compared to the number of live plants in a pot kept for comparison under the same conditions but treated with an active ingredient spray. In this way one determined the percentage extinction of the plants, relative to the untreated control pot. A percent kill of 100% means that the plant species in question has been completely destroyed; a percent kill of 0% means that the number of live plants in the pot treated was equal to the number in the control pot.

The experiments carried out thus show the remarkably advantageous properties of the invention

20 according to provided active ingredients both in the pre-emergence treatment of crops, as well as in postemergence treatment of soybean, cereals, such as corn, sunflower, cotton and beans. In the case of soya, the activity of the invention provided

It is of particular interest when the soy plantations are infested with dicotyledonous weeds, such as Indian mallow, Norway spike and purple winds.

Tables 1 to 3

- 38 Table 1

Connection R ¹ R ² Yield% Fp ⁰ C 1 CH ₃ Cl 96 83 2 CH 3 CH 0- 65 126 3 CH ₃ C ₂ H ₅ O- 54 102 4 CH ₃ (CH ₃ ) ₂ CHO- 37 125 5 C ₂ H ₅ CH ₃ O- 45 112 6 ClCH ₂ CH ₃ O- 54 127 7 CH ₃ O- 29 100 8th "о- CH ₃ O- 49 viscous product 9 CH ₃ ClCH ₂ CH ₂ O- 71 101 10 CH ₃ CH ₃ OCH ₂ CH ₂ O- 34 128 11 CH ₃ CCl ₃ CH ₂ O- 67 177 12 сн ₃ CF ₃ CH ₂ O- 92 144 13 сн ₃ CH ₂ = CHCH ₂ O- 46 88 14 сн ₃ HC = C-CH ₂ O- 67 134 15 сн ₃ C ^ H ₁ -O ₀ CCHO- ^{1 ь l} ₃ OH 60 viscous product 16 сн ₃ CH ^ .0 ~ - ₁ ^ ^CH 2 ° CH ^ O > 73 68 17 сн ₃ (CH ₃ J ₂ C = NO- Q 91 viscous product 18 сн ₃ 39 95

Table 1 (continued)

Connection R ¹ R ² Yield% Fp ⁰ C 19 CH ₃ HS 44 182 20 CH ₃ NaS- 93 220 21 CH ₃ CH ₃ S- 75 47 22 CH ₃ C ₂ H ₅ -O-OC-CH ₂ -S 70 91 23 CH ₃ C-IU-O-OC-CH-S- ^D CH ₁ 98 viscous product 24 CH ₃ JH ₂ N 80 79 25 CH ₃ (CH ₃ ) HN- 76 75 26 CH ₃ (CH ₃ ) ₂ N- 61 69 27 CH ₃ (HO) HN 100 150 28 CH ₃ CH.-O-OC-CH-O-NH- ₃ 34 viscous product 29 CH ₃ CH ₃ SO ₂ -NH- 29 211 30 CH ₃ (CH ₃ SO ₂ ) NaN 100 110

crops

Table 2

Wheat soy

weeds:

Chicken millet Echinochloa crus-galli

Indian mallow Abutilon theophrasti

Spitzklette Ackersenf Purple Winds Raygras Cypergras

Xanthium pennsylvanicum Sinapis arvensis Ipomea purpurea Lolium multiflorum

EC AT XP SA IP LM CY

Table 3

Connection 4 Dose kg / ha preemergence EC LM AT IP SA XP WE so Nacftauflauf EC LM AT IP SA XP CY V7E ' SO 0 1 4 1 0.25 0 2 4 1 0.25 100 100 100 100 100 100 100 0 100 30 100 80 100 100 50 50 30 3 4 1 0.25 100 50 100 80 100 60 20 0 100 0 50 80 100 100 0 0 0 4 1 0.25 100 100 100 30 100 0 90 80 100 100 100 100 100 100 0 20 0 100 100 100 0 98 0 60 100 60 80 100 100 100 100 0 0 0 100 90 100 0 98 0 60 0 50 40 80 100 100 100 0 0 0 95 98 100 0 50 0 20 0 80 50 100 100 70 90 0 0 0 60 80 100 0 0 0 0 0 30 0 20 100 30 90 0 0 0 50 ^ 50 100 0 0 0 0 I 0 20 0 0 90 30 80 0 0 0 40 0 100 0 0 0 0 0 20 20 0 50 60 100 0 0 0 0 0 100 0 0 0 0 0 0 20 0 0 50 80 0 0 0 0 100 0 0 0 0 0 0 20 0 0 50 100 0 0

Table 3 (continued)

Connection Dose kg / ha preemergence EC LM AT IP SA XP WE so postemergence EC LM AT IP SA XP WE so 0 5 2 0.5 0.125 80 90 100 80 80 90 30 0 20 30 80 90 90 10 0 6 2 0.5 0.125 60 80 100 30 90 0 10 20 80 100 90 0 0 7 2 0.5 0.125 20 40 90 50 20 0 0 10 10 10 10 70 0 0 8th 2 0.5 0.125 50 50 80 90 80 0 20 20 20 70 100 0 0 40 40 90 60 50 0 10 10 10 40 90 0 0 0 0 90 50 0 0 0 0 0 0 60 0 0 0 0 100 0 20 0 0 40 0 80 100 100 0 0 0 0 20 0 0 0 0 20 0 80 90 50 0 0 Q 0 0 0 0 0 0 0 0 20 80 0 0 0 30 10 20 30 100 0 0 50 20 70 90 100 0 0 0 10 20 20 0 0 0 20 0 50 70 90 0 0 0 0 10 0 0 0 0 10 0 20 0 10 0

Table 3 (continued)

Connects. 'dung Dose in preemergence EC LM AT IP SA XP WE so postemergence FC LM AT IP SA XP I WF, so kg / ha 100 98 100 90 95 0 0 40 80 50 100 100 0 0 9 4 50 60 98 0 95 0 0 20 50 30 80 95 0 0 10 1 0 0 50 0 0 0 0 0 0 0 100 30 0 0 11 0.25 100 100 100 100 100 20 0 100 60 80 100 100 20 0 12 2 100 50 100 50 100 0 0 20 30 30 80 100 0 0 0.5 20 0 80 0 100 0 0 0 0 20 30 60 0 0 0,125 50 0 100 80 100 100 0 50 20 0 0 80 100 100 0 0 4 0 0 100 100 100 80 0 50 0 0 0 80 90 50 0 0 1 0 0 90 0 90 80 0 0 0 0 0 80 0 0 0 0.25 30 0 80 60 80 100 0 50 0 0 0 60 80 50 0 0 4 30 0 90 90 80 100 0 0 0 0 0 20 0 0 1

Table 3 (continued)

Connection Dose in kg / ha preemergence EC LM AT IP SA XP WE ! so postemergence FC LM AT IP 100 SA XP WE so 13 4 1 0.25 90 30 95 0 100 50 0 0 60 30 100 30 100 100 l * - 80 0 0 14 4 1 0.25 60 0 80 0 0 0 0 30 30 50 98 100 100 0 0 15 4 1 0.25 0 0 80 0 0 0 0 0 20 0 20 20 100 100 50 0 0 16 2 0.5 0.125 0 0 50 50 80 100th 0 100 0 0 30 50 80 100 100 0 0 0 0 0 0 30 0 0 0 0 0 0 0 80 80 100 0 0 0 0 0 0 0 0 0 0 0 0 0 0 60 30 0 0 100 98 100 100 100 0 20 100 40 100 100 0 0 100 20 95 100 100 0 0 100 30 100 100 0 0 30 0 80 20 100 0 0 100 0 98 100 0 0 20 0 98 0 95 0 0 30 о 50 100 20 0 0 0 80 0 0 0 0 20 0 30 0 0 0 0 0 50 0 0 0 0 0 0 0 Q о І 0

Table 3 (continued)

Connection Dose in kg / ha preemergence EC LM AT IP SA XP WE so t postemergence EC LM AT IP 100 SA I XP WE so 0 17 2 0.5 0.125 100 100 100 100 100 80 , 0 100 20 100 100 100 100 20 0 18 2 0, 5 0.125 100 30 100 100 100 0 0 98 20 100 100 100 100 20 0 19 4 1 0.25 0 0 100 0 100 0 0 20 0 30 100 100 100 0 0 20 4 1 0.25 100 100 100 100 100 100 0 100 30 90 100 100 20 0 100 100 100 100 100 0 0 98 ⁰ 20 100 100 0 0 80 0 98 50 100 0 0 20 0 0 90 90 0 0 100 80 100 100 100 .80 5σ • 0 100 20 100 100 100 100 20 0 90 30 100 100 100 0 0 0 90 0 100 y. 100 100 100 0 0 30 0 98 50 100 0 0 0 30 0 100 100 100 0 0 100 50 100 100 100 100 0 100 90 20 100 100 100 0 0 90 0 100 100 100 100 0 80 80 20 100 100 100 0 0 30 0 95 80 100 100 0 100 20 0 80 100 100 0

Table 3 (continued)

Connection Dose. in kg / ha preemergence EC LM AT IP SA XP WE so postemergence EC LM AT IP SA XP ViE so 21 4 1 0.25 80 80 100 50 98 0 0 0 30 20 100 100 100 0 0 0 22 2 0.5 0.125 70 20 100 50 90 0 0 0 30 0 90 100 100 0 0 0 23 2 0.5 O> 125 30 0 100 0 30 0 0 0 30 0 90 80 100 0 0 0 24 4 1 0.25 90 20 0 0 100 0 0 100 30 80 30 100 0 0 0 0 0 0 100 0 0 100 20 50 30 100 0 0 0 0 0 0 100 0 0 80 0 0 20 100 0 0 90 60 100 0 100 0 0 100 40 90 80 100 20 0 0 0 20 0 100 0 0 100 30 40 40 100 0 0 O ⁴ 0 0 0 100 0 0 20 0 20 0 100 0 0 100 80 100 100 100 80 30 0 90 0 100 100 100 100 0 0 30 0 60 0 100 0 0 0 30 0 100 50 30 100 0 0 0 0 60 0 100 0 0 0 0 0 ⁰ 50 20 0 0 0

Table 3 (continued)

Connection Dose in kg / ha preemergence EC LM AT IP SA XP WE so postemergence EX LM AT IP SA XP WE so 25 4 1 0.25 90 80 100 50 100 0 30 0 20 0 30 50 0 0 0 0 26 4 1 0.25 0 0 0 0 95 0 0 0 0 0 0 50 0 0 0 0 27 2 0.5 0.125 0 0 0 0 30 0 0 0 0 0 0 30 0 0 0 0 28 2 0.5 0.125 90 70 100 0 100 0 30 0 20 0 40 50 20 0 0 0 0 0 95 0 100 0 0 0 0 0 0 0 20 0 0 0 0 0 40 0 30 0 0 0 0 0 0 0 20 0 0 0 100 90 100 100 100 50 0 LOO 0 80 100 100 0 0 30 0 0 20 100 0 0 30 0 30 100 100 0 0 0 0 0 0 80 0 0 20 0 0 100 30 0 0 50 0 100 100 100 0 0 40 20 100 100 0 0 0 0 50 0 20 0 0 30 0 100 100 0 0 0 0 0 0 0 0 0 20 0 100 100 0 0

Table 3 (continued)

Connection Dose in kg / ha preemergence EC LM AT IP 100 SA XP WE so postemergence EC LM 0 AT ΓΡ SA XP I WE so 29 2 0.5 0.125 70 50 100 70 70 100 10 0 30 0 50 100 100 10 0 30 2 0.5 0.125 30 30 90 0 40 100 0 0 10 0 3C 90 100 0 0 0 0 70 0 100 0 0 0 20 10 100 80 0 0 60 60 100 100 10 0 40 0 60 100 100 0 0 30 30 100 100 0 0 20 0 20 90 90 10 0 30 30 100 100 0 0 20 θ! 50 50 0 0

Claims (11)

invention claim 1. A herbicidal composition containing an active ingredient, combined with at least one inert conventional, agriculturally acceptable carrier, characterized in that the active ingredient of the general formula "= N-S0 ₂ -R ¹ (D in which W, Ϋ, Y ¹ , X, Z ¹ and Z are each a hydrogen or a halogen atom or an NO-, or CN-group or a polyhaloalkyl group, or an alkyl or alkoxy group, where the different alkyl or alkoxy groups usually have 1 to 4 carbon atoms, SO -X- R is an alkyl, alkenyl, alkynyl or phenyl group which is optionally substituted, R is a halogen atom or one of the groups CN, SCN, OR, SR ⁴ or NR ⁵ R ⁶ , R is an optionally substituted alkyl group or an allyl, propargyl, alkylcarbonyl, alkylidene imino group or represents the succinimido group, 4
R is hydrogen or a cation or one of the has meanings given for R, R is a hydrogen atom or an optionally substituted alkyl group or an alkylcarbonyl or alkylsulfonyl group, R has one of the meanings given for R or is a cation or the group CN or the group OR, where R stands for a hydrogen atom or for a cation or for an alkyl group, a carboxylic acid ester group or a carboxamido group or an alkylcarbonyl group. 2. A herbicidal composition according to item 1, characterized in that in the active ingredient 20 given formula (I) W is a hydrogen or a halogen atom, in particular Cl, Br or F or the NO_ or CN group, Y is a hydrogen or halogen atom, in particular Cl, Br or F or one of the groups N0-, CN, CF .. or CH-, Y ¹ , Z ¹ and Z are each a hydrogen or a halogen atom, in particular Cl, Br or F, X is a halogen atom, in particular Cl, Br or F or one of the groups Ν0_, CF-, CH ₃ or C ₃ H ₅ , R is an alkyl group having usually 1 to 12 carbon atoms and preferably 1 to 6 carbon atoms, optionally with one or more halogen atoms, in particular Cl, Br or F or by
one or more alkoxy or alkylthio groups with Si usually 1 to 4 carbon atoms or with one or more groups CN or with a phenyl group is substituted, which in turn is optionally substituted, especially with one or more halogen atoms or an alkenyl or alkynyl group having usually 2 to 4 carbon atoms, in particular the vinyl, ethynyl, allyl or propargyl group or a phenyl group, which in turn may be substituted, especially with one or more halogen atoms or with nitro groups or with alkyl groups, which usually have 1 to 4 carbon atoms; 2
R is a halogen atom, preferably chlorine or one of Groups CN, SCN, OR ³ or SR ⁴ or NR ⁵ R ⁶ ; R is an alkyl group which usually has 1 to 4 carbon atoms and is optionally substituted by: one or more halogen atoms, in particular Cl, Br or F or with
one or more alkoxy or alkylthio groups, which usually have 1 to 4 carbon atoms or with one or more N0-, - or CN groups or with a carboxylic acid group or one of its derivatives of the salt, ester or amide type, in particular a group COOR, where R is a hydrogen atom or an alkyl group having usually 1 to 4 carbon atoms or a metal cation or the ammonium cation or with an alkylcarbonyl group, in particular the acetyl group or with
a phenyl group, which in turn may be substituted, especially with one or more halogen atoms or with a group sz in which R and R may be identical or different and each represents a hydrogen atom or an alkyl group having usually 1 to 4 carbon atoms or R is an allyl or propargyl group or an alkylcarbonyl group, in particular the acetyl group or a group 8 9
wherein R and R are as defined above; 4
R is a hydrogen atom or an alkali cation or the ammonium cation or has one of the meanings given for R, R is a hydrogen atom or an alkyl group having usually 1 to 4 carbon atoms, which is optionally substituted by a carboxylic acid group or its derivatives of the salt, ester or amide type, especially by a group COOR, wherein R has one of the meanings already indicated or an alkylcarbonyl or alkylsulfonyl group, especially the acetyl group or methanesulfonyl group; R has one of the meanings given for R, or an alkali cation or the ammonium cation, or the group CN or a group OR, where R has one of the following meanings:
Hydrogen atom or 30 an alkali cation or the ammonium cation or an alkyl group having usually 1 to 4 carbon atoms, which is optionally substituted by a carboxylic acid group or one of its derivatives of the salt, ester or amide type, in particular a COOR group, in which R is one of the 35 already given above meanings or 7 7 7 a group COOR or CONHR, where R is one of the above has specified meanings or an alkylcarbonyl group, especially the acetyl group. 3. A herbicidal composition according to one of the items 1 or 2, characterized in that in the formula (I) for the active ingredient X is Cl or CF, Y ¹ and Z ^{1 are} each H, Y is Cl, Z is the Meaning Cl or F or H and W stands for N0. 4. A herbicidal composition according to one of the items 1 to 3, characterized in that in the for the 2 active ingredient given formula (I) R for Cl or one of Groups OR ³ , SR ³ or NR ⁵ R ⁶ , R ¹ , R ³ and R ^{6 are} each 4 5 alkyl groups, R and R each represent a hydrogen atom or a methanesulfonyl group and R is a hydrogen atom or an alkali cation or the ammonium cation. 5. A herbicidal composition according to any one of items 1 to 4, characterized in that X is CF-, Z is H and R is an alkoxy group. 6. Herbicidal agent according to one of the items 1 to 5, characterized in that R is SH 5 and the active ingredient is in a tautomeric form. 7. A herbicidal composition according to any one of items 1 to 6, characterized in that it contains 0.5 to Contains 30 95% active ingredient. 8. A herbicidal composition according to any one of items 1 to 7, characterized in that it contains 1 to 95% carrier and 0.1 to 20% surfactant 35 contains. 9. Application of the herbicidal composition according to any one of items 1 to 8 for selective weed control in crops. 10. The use according to item 9, characterized in that the active compound of the general formula (I) is applied in an application rate of 0.01 to 5 kg / ha, preferably 0.1 to 2 kg / ha. 11. Use according to item 9 or 10 in a soybean culture or a cereal culture, in particular a maize culture or in a sunflower, cotton or bean culture.