DK144321B - HERBICID CONTAINING AS AN ACTIVE INGREDIENT A SUBSTITUTED 2,1,3-BENZOTHIADIAZINE (4) ON-2,2-DIOXIDE - Google Patents

Description

(19) DENMARK \ la7 ® (, 2) PUBLICATION <„> 144321b

DIRECTORATE OF THE PATENT AND TRADEMARKET SYSTEM

(21) Application No. 4184/75 (51) Int.CI.3 A 01 N 43/88 (22) Filing Date 18 Sep. 1975 A01 N 47/08 (24) Race day 18 Sep. 1975 A 01 N 47/44 (41) Aim. available Mar 20 1976 a 01 N 57/32 (44) Submitted Feb 22 1982 // C 07 D 285/16 (86) International Application No. - C 07 F 9/65 (86) International Filing Day “(85) Continuation Day - (62) Stock Application No. ~

(30) Priority 19 · Sep. 1974, 2444822, DE

(71) Applicant BASF AKTIENGESELLSCHAFT, 6700 Ludwigshafen, DE.

(72) Inventor Adolf Fischer, DE: Adolf Zeidler, DE: Gerhard Hamprecht, DE: Peber Schmidt, DE.

(74) Associate Engineer Hofman-Bang & Boutard.

(54) Herbicide containing as an active ingredient a substituted 2,1,3-benzothiadiazine (4) one-2,2-dioxide.

The invention relates to a novel valuable herbicide which contains as an active ingredient a substituted 2,1,3-benzothiadiazine (4) -one-2,2-dioxide with herbicidal activity.

It is known that 3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxide can be used as herbicide active substance (German Patent No. 1,542,836). However, its use in practice leads to damage of the treated plants.

N

Nu It has now been found that a herbicide of the kind specified in the preamble of claim, which is peculiar to the characterizing portion of the claim, exhibits a better herbicidal effect than the known active substance.

For example, R 2 may mean: formyl, propionyl, sec.-valeryl, pelargonyl, palmityl, acetoxyacetyl, chloroacetyl, dichloroacetyl, Λ-chloropropionyl, d., C-dichloropropionyl, chloro-butyryl, -chloropropionyl, N-alpha-bromobutyryl, phenoxyacetyl, p-chlorophenoxy-oxyacetyl, 2,4-dichlorophenoxyacetyl, 2,4,5-trichlorophenoxyacetyl, 2-methyl-4-chlorophenoxyacetyl, 2,4,5-trichlorophenoxyacetyl, 2-methyl-4-chlorophenoxyacetyl , 2,4-dichlorophenoxy-c c-propionyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butcycycarbonyl, tert-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, n-pentyloxycarbonyl, pentyl (3) oxyc , cyclohexyloxycarbo-nonyl, n-heptyloxycarbonyl, n-heptyloxycarbonyl, n-octyloxycarbo-nonyl, n-nonyloxycarbonyl, n-decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, tridecyloxycarbonyl, tetradecyloxycarbonyl, pentadecyloxycarbonyl, hexadecyloxycarbonyl, methylmercaptocar-carbonyl, ethylmercaptocarbonyl, n-propyl lmercaptocarbonyl, isopropyl mercaptocarbonyl, n-butyl mercaptocarbonyl, p-chlorobenzylmercaptocarbonyl, dimethylcarbamoyl, diethylcarbamoyl, di-n-propylcarbamoyl, diisopropylcarbamoyl, di-n-butylcarbamoyl, di-sec-N-sec-N-sec -propoxymethylcarbamoyl, dimethylthiocarbamoyl, diethylthiocarbamoyl, di-n-propylthiocarbamoyl, diisopropylthiocarbamoyl, N-phenyl-N ', N'-dimethylformamidinyl, methanesulfonyl, ethanesulfonyl, 2-propanesulfonyl, 1-propanesulfonyl , isobutanesulfonyl, 2-butanesulfonyl, 1-pentanesulfonyl, benzenesulfonyl? p-toluenesulfonyl, o-, m-, p-bromobenzenesulfonyl, 0-, m-, p-nitrobenzenesulfonyl, β-naphthalenesulfonyl, N-methyl-benzimidyl, N-ethylbenzimidyl, N-propylbenzimidyl, 0,0-dimethyl-thiophosphoryl and 0, O-diethyl thiophosphoryl.

Examples of substituted 2,1,3-benzothiadiazine (4) on-2,2-dioxides included in the herbicide according to the invention should be mentioned:

mp, ° C

1-methylaminosulfonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide 151 - 153 1-isopropylaminosulfonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2, 2-Dioxide 151 - 153 3 144321 2

The preparation of the compounds of formula IV, wherein R is a substituted acyl or aroyl group, can be carried out, for example, by reacting a 3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide-1-alkali metal - (or alkaline earth metal) or -ammonium salt of formula II and a substituted acyl halide I in a polar solvent in a temperature range of -10 to 110 ° C between half and 12 hours: RC-Hal + VnV *) - **, \ LjU "

Me 0 = C-R

I. II IV

where Me is an equivalent of an alkali metal ion or an alkaline earth metal ion or ammonium and Hal is a chlorine atom or bromine atom and n where R-CO- has the meaning specified in R for (a).

= - isopropyl.

For reprocessing, the precipitated metal or ammonium salt is optionally separated and evaporated in vacuo. The purification is carried out by recrystallization or by extraction with dilute alkali and neutral washing of water-immiscible solvents. In the latter case, the pure compounds IV are isolated after the drying and evaporation of the organic phase.

However, instead of the starting substance II, it is also possible to directly react the substance of formula III which forms the substance in question with a substituted acyl halide I in the presence of a tertiary base under the above conditions:

R-C-Hal + Y

/ * II J - HHal 'o A J »

H 0 = C-R

I III IV

4 U4321 thereby. Hal represents a chlorine atom or a bromine atom, whereby R-CO-p has the meanings set forth in the requirement for R under (a).

The purification is carried out in the usual manner by extraction of the water-soluble base hydrochloride and work-up according to the above procedure.

In the case of the preparation of 1-formyl-3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxides YI, synthesis is carried out by reaction between the starting material III and the mixed formic acid-acetic anhydride. V and work-up according to the above procedure,

HC-O-C-CH, + - * VirV ^ I

H. 0 = C-H

. · V III -. WE

Reaction of 2 equivalents of 3-isopropyl-1,2,3-benzothiadiazine (4) on-2,2-dioxide-1-sodium salt II with an equivalent of oxalyl chloride VII according to the above reaction conditions gives the compound with formula VIII

o Γ o

Wr \ + Cl-C-C-Cl - ^

Na C = 0 2 t

II VII VIII

To prepare substituted 1-alkoxy or aryloxycarbonyl or alkylmercapto-carbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxides X, the starting salts of formula II are reacted with correspondingly substituted chloroic acid esters IX according to the above reaction conditions, whereby Me is the equivalent of an alkali metal ion or alkaline earth metal ion or ammonium and -CO-OR or -CO-SR has the meanings specified in the requirement of R under b).

o o 9 / To 1 + ci-c-or - / i 11 -SR ° 2δ>, ϊΓ ^

Me 0 = C-OR

-SR

II IX X

By analogy, by reacting compounds II with optionally substituted dialkylcarbamoyl, -thio-carbamoyl chlorides or N-phenyl-N ', N'-dialkylchloroformamidines XI, to compounds XII, where Me represents an equivalent of an alkali metal ion or alkaline earth metal ion or ammonium, and wherein 0 (S) (N-phenyl) -C-NAlk 2 0 has the meanings specified in the requirement for R under c).

0 O

\ 9 (S) i (N-Phenyl! \ X ^ jj J + Cl-C-NAlk2 - * / T ifj

2S °

1 I

Me (phenyl-N); (S); 0 = C-NAlk2 ii xi xii

By reaction of optionally substituted alkane or arene sulfonyl chlorides XIII with the starting compounds II, compounds of formula XIV are obtained in an analogous manner, whereby Me represents an equivalent of an alkali metal ion or alkaline earth metal ion or ammonium, and -SOgR

6 144321 p has the meanings specified in the requirement for R under (d): ιύο * ^ - ϊ? 5ο in »

Me S02R

II XIII XIV

In the case of monoalkylsulfamoyl chlorides XV, when used in the above-described manner to compounds XVI, where Me represents an equivalent of an alkali metal ion or alkaline earth metal ion or ammonium and wherein -SO 2 -NHAlk has it in the requirement of R (e) the meaning indicated:.

O: * - vpO

'SOg-NHAlk

II XV XVI

Analogously reacting N-alkyl benzimide chlorides XVII with starting salts II gives 1- (N-alkyl-benzimidyl) -3-isopropyl-2,1,3-ene-2 -othiadiazine (4) on-2,2-dioxides of formula XVIII, whereby Me represents an equivalent of an alkali metal ion or alkaline earth metal ion or ammonium, and wherein -C = N-Alk ό 7 144321 has the meaning given in subparagraph (f): φθ * Φ £, · “- φδ

Me σ C = N-Alk

II XVII XVIII

Analogously reacting the starting salts II with a dialkyl phosphoric acid ester halide gives 1-0.0-dialkylthiophosphoryl-3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxides XXII Me means an equivalent of an alkali metal ion or alkaline earth metal ion or ammonium ion, whereby -P = (OAlk) 5

If ^

S

has the meaning given in subparagraph (g): S S o> - ^ ΎΊ + Hal-P = (OAlk) - ·) -fVb

° 2SY ^ »aVV

Me · S = P (0Alk) 2

II XXI XXII

The starting materials II or III can be reacted with the desired acid chlorides in stoichiometric amounts or with an excess of acid chloride, preferably in a ratio of 1.01 to 1.2 moles of acid chloride per liter. moles of starting material II or III. The preparation of the starting materials II and III is described in U.S. Patent No. 3,041,336 and in German Patent No. 1,542,836.

8 144321

As a tertiary base for the reactions with the starting materials III are, for example: trimethylamine, triethylamine, pyridine, α, β, ρροοοίίη, lu-tidin, N, N-dimethylaniline, N, N-dime thylcyclohexylamine, quinoline, isoquinoline, quinazoline, tri -n-butylamine, tri-n-propylamine and N-propyl diisopropylamine are suitable.

As polar solvents can be used chlorobenzene, o-, m-, p-dichlorobenzene, nitrobenzene, anisole, toluene, methylene chloride, chloroform, 1,1- and 1,2-dichloroethane, 1,1,2-trichloroethane, 1,1 , 2,2- and 1,1,1,2-tetrachloroethane, substituted carbonamides such as N-methyl and N, Ν-dimethylformamide, ketones such as acetone, methylethyl ketone, acetophenone, cyclohexanone, esters such as methyl acetate, isobutyl acetate, ethers as diethyl ether, di-n-propyl ether, dioxane and tetrahydrofuran and nitriles such as acetonitrile, isobutyronitrile and benzonitrile.

The reactions are generally carried out in a temperature range between -10 and 70 ° C, preferably between 0 and 40 ° 0; however, with less reactive acid chlorides, heating to 110 ° C may also be necessary.

EXAMPLE 1 Formula - isopropyl-P, 1 ± 3 R 2 gnzpthiadiazine (4) onion 32 parts (parts by weight) of a 30% by weight solution of the mixed formic acid acetic anhydride (made from equimolecular amounts formic acid and acetic anhydride) in a mixture of formic and acetic acid is added at room temperature to a solution of 24 parts of 3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxide in 120 parts of acetonitrile. The reaction mixture is stirred for 3 hours at 50 ° C and then evaporated in vacuo. The residue is taken up in methylene chloride, extracted four times with 0.5N sodium hydroxide solution and with water and dried over magnesium sulfate. After evaporation in vacuo, 24 parts of (• 90% of the theoretical amount) of 1-formyl-3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxide are obtained as colorless crystals, m.p.

90 to 99 ° C (decomp.).

g 144321 EXAMPLE 2

Within 15 minutes and at 15 to 20 ° C, a quantity of I is allowed to run to a solution of approx. the equimolar amount of II in an amount of acetonitrile corresponding to ca. the double amount of I + II. The reaction mixture is kept under stirring for one hour at 20 ° C and then freed of solvent in vacuo. The residue is taken up in methylene chloride, extracted four times with 5 per cent. sodium carbonate solution, washed with water and dried over magnesium sulfate. After evaporation in vacuo, an amount is obtained, e.g. corresponding to 81 per cent. of the theoretical value of IV, e.g. as a colorless, viscous oil. After rubbing in cyclohexane, colorless crystals are obtained which can be characterized by their melting point.

In this way, the following compounds were prepared:

Mp. (° C) 1-propionyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2.2-dioxide 103 - 105 1-sec-valeryl-3-isopropyl-2,1,3 ”benzothiadiazine (4) 1-valeryl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2.2-dioxide 39-44 1-oapronyl-3-isopropyl-2,1 3-Benzothiazole] -one-2,2-dioxia 67 _ 63

1-pelargonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-9C

2,2-dioxide n 2 = 1,5128 1-palmitoyl-3-isopropyl-2,1,5-benzothiadiazine (4) one-2.2-dioxide 65-67 1-acetoxyacetyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2.2-dioxide 69-73 1-chloroacetyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2.2-dioxide 106 - 109 1-a-chloro-propionyl-3-isopropyl-2 , 1,3-benzothiadiazine (4) one-2,2-dioxide 83-85 1-pent-3'-enoyl-3-isopropyl-2,1,3-benzothiadiazine (4) - 25.

1-Phenoxyacetyl-3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide 111 - 116 1-p -chloroplienoxyacetyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide 106 - 111 1 -2 ', 4' -dichlorophenoxyacetyl-3-isopropyl-2,1,3 -benzothiadiazine (4) one-2,2-dioxide 138 - 143 1 -2 ', 41,5T-trichloroplienoxyacetyl-3-isopropyl-2,1', 3-benzothiadiazine (4) one-2,2-dioxide 164 - 170 1 -2 '-Methyl-4' -chloroplienoxyacetyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide 161 - 163 1- (21,4 ') -dichlorophenoxy) propionyl-3-ispropyl-2,1,3-benzothiazadiazine (4) one-2,2-dioxide 105 - 108 oxalyl-bis-1- [3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide] 223 - 224 (decomp.) EXAMPLE 3 1-a-T3romobutyryl-5-isopropyl-2j. 1A3-benzothiazadiazine (4) on-2,2-dioxide

Within 10 minutes and at 10 ° C, 22.9 parts of α-bromobutyric acid bromide are allowed to run to a solution of 24 parts of 3-iso-propyl-2,1,3-benzothiadiazine (4) on-2,2-dioxide and 10.1 parts of triethylamine in 130 parts of acetonitrile. The reaction mixture is kept under stirring for 10 minutes at 20 ° C and then suctioned. The filtrate is then evaporated in vacuo, taken up in benzene and washed twice with 5 per cent. sodium bicarbonate solution and twice in water. After drying and evaporation, the 1-a-bromobutyryl-3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxide is obtained as a colorless oil (n petrol ether crystallizes with melting point 73 - 78 ° C.

EXAMPLE 4 1- N -Butoxy-carbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-άϊοχί (1 ____)

To a solution of 26.2 parts of 3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide-1-sodium salt in 120 parts of acetonitrile, a solution of 15 parts of chloroformic acid n-butyl ester in 15 parts of acetonitrile run at 20 ° C. The reaction mixture is kept under stirring for 1 hour at 20 ° C and for 2 hours at 65 ° C. After evaporation in vacuo, the residue is taken up in methylene chloride, extracted three times with 0.3 N sodium hydroxide solution and with water and dried over magnesium sulfate. Evaporation gives 1-n-butoxycarbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide as a viscous oil which crystallizes on rubbing in petroleum ether with melting point 48-54 ° C .

Similarly, the following compounds were obtained:

Mp. (° O) 1-Methoxycarbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) - 103 - 105one-2,2-dioxide 1-ethoxycarbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) ) - one, 2,2-dioxide 109 '120 1-hexadecoxycarbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide 66-68 1-phenoxycarbonyl-3-isopropyl-2 1,3-Benzothiadiazine (4) -one-2,2-dioxide 111 "115 1-methylmercaptocarbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide 117 121 ln-propylmercaptocarbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide n 2 (4) -one-2,2-dioxide 98 - 100 12 UA321 EXAMPLE 5 1-Dimethylcarbamoyl-3-isopropyl-2? 1? 3-benzothiadiazine (4) -one-2? 2-dioxide 13.9 parts 3- Isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide potassium salt was heated in 15 parts of dimethylcarbamic acid chloride for 5 hours to 100-110 ° C. 150 parts of a 1: 2 mixture of benzene were added. ether and suctioned the potassium chloride from (3.6 parts). The iltrate was mixed with 100 parts of a 1: 2 mixture of ther and petroleum ether; then the crystalline product was suctioned off and recrystallized from cyclohexane. 1-dimethylcarbamoyl-3-iso-propyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide was obtained, m.p. 83 - 85.5 ° C.

Similarly, the following compounds were obtained:

Mp, (° O) 1-diethylcarbamoyl-3-isopropyl-2,1,3-benzothiadiazine- (4) one-2,2-dioxide 100 - 104 1-diisopropylcarbamoyl-3-isopropyl-2,1,3-benzothia - diazine (4) one-2,2-dioxide 150 - 152 1-N-methyl-Nn-propoxymethylcarbamoyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide D ' 1-Dimethylthiocarbamoyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide 78-81 1- [N * -phenyl-N ", N" -dimethylformamidinyl] -3-isopropyl - 2,1,3-benzothiadiazine (4) on-2,2-dioxide Example 6

IzSÉi ^^ SHiiESlil zisopropyl ^ - ^^ IS-on- benzotMadiazin ^^ ^ g-dioxide

To a solution of 26.2 parts of 3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide sodium salt in 120 parts of acetonitrile is allowed to stir within 10 minutes at 20 ° 0 12, 6 parts of methanesulfonyl chloride are added. The reaction mixture is kept under stirring for half an hour at 20 ° C and 2 hours at 60-65 ° C. Now the separated boiling salt is suctioned off and the filtrate is evaporated in vacuo. The residue is subjected to rubbing in ether, suctioned and washed neutral with water to give the 1-methanesulfonyl-3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxide in the form of colorless crystals with m.p. 156 - 158 ° C.

By analogy, the following compounds were prepared:

Mp. (° G) 1-Ethanesulfonyl-3-isopropyl-2,1,3-benzothiadiazine- (4) one-2,2-dioxide 110 - 112 1-isobutanesulfonyl-3-isopropyl-2,1,3-benzothiadiazine- ( 4) one-2,2-dioxide 103 - 110 1-benzolsulfonyl-3-isopropyl-2,1,3-benzothiadiazine- (4) one-2,2-dioxide 162-166 1-ptoluolsulfonyl-3-isopropyl-2,1 3,3-benzothiadiazine (4) one-2,2-dioxide 141 - H3 1-p-bromobenzol sulfonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide 163 - 168 1-p-nitrobenzene sulfonyl-3-isopropyl-2,1,3-benzothiadiazoline (4) one-2,2-dioxide 160 - 175 Ι-β-naphthalene sulfonyl-3-isopropyl-2,1,3-benzothiadia zin (4) one-2,2-dioxide 106 EXAMPLE 7 1- [N-methyl-benzimidyl] -3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide ___________________________________________________

A solution of 26.2 parts of 3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide-1-sodium salt in 120 parts of acetonitrile is allowed to settle at 15-20 ° within 10 minutes under stirring run to 15.4 parts of N-methyl-benzimide chloride in 120 parts of acetonitrile. The reaction mixture is stirred for one hour at 20 ° C and then evaporated in vacuo. The residue is taken up in methylene chloride, extracted four times with 10 pot. sodium carbonate solution, washed with water and dried. After evaporation in vacuo, the 1- [KT-methyrbenzimidyl] -5-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxide is isolated as a viscous oil which crystallizes by rubbing in petroleum ether , m.p. 85 - 95 ° 0. One of the cyclohexane recrystallized sample melts at 96 - 103 ° C.

EXAMPLE 8 1-0,0-Diethylthiophosphoryl-3-isopropyl-2,1,3-benzothiadiazine in 25-1 2Z 2- dioxide ± 18.9 parts of 0.0-diethylthiophosphoric acid chloride was left at room temperature added to a solution of 26.2 parts of 3-isopropyl-2,1,3-benzothiazine (4) one-2,2-dioxide-1-sodium salt in 120 parts of acetonitrile. The reaction mixture is stirred for 12 hours under reflux. Then it is evaporated in vacuo, absorbed in benzene and extracted twice with water, twice with 10 per cent. sodium bicarbonate solution and twice with water. After drying and evaporation, 1-O-diethyl-thiopbosphoryl-3-isopropyl-1,1,3-benzothiadiazine (4) on-2,2-dioxide is obtained as viscous oil with n 2 = 1.5219.

Analogously, the following compound was prepared: 1-0.0-dimethyl-thiophosphonyl-3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide, nD25 = 1.5424

The dispensing is carried out, for example, in the form of directly sprayable solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, powders, scavengers, granules by spraying, misting, spraying or spraying. The forms of dispensing are entirely directed to the uses; they must in each case ensure the finest possible distribution of the active substances according to the invention.

In the preparation of directly sprayable solutions, emulsions, pastes and oil dispersions, medium to high boiling mineral oil fractions such as kerosene or diesel oil, in addition to coal and petroleum oils> and vegetable or animal origin oils, aliphatic, cyclic and aromatic hydrocarbons, e.g. . "benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, for example methanol, ethanol, propanol, butanol, chloroform, tetrachlorocarbon, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, highly polar solvents such as f. eg dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water considered.

Aqueous dispensing forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders), oil dispersions by the 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 wetting, adhesive, dispersing or emulsifying agents.

However, concentrates of active substance, wetting or emulsifying agents and optionally solvents or oil may also be prepared which concentrates are suitable for dilution with water.

Examples of surfactants are:

Alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acids, phenolic sulfonic acids, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutyl naphthalenesulfonic acid, lauryl ether sulfate acid, lauryl ether sulfate acid, lauryl ether sulfate acid heptadecanols, octadecanols, salts of sulphated fatty alcohol glycol ether, condensation products of sulphonated naphthalene and naphthalene ethanol octylphenol oxyphenol oxyphenol ether, polyoxyethylene octylphenol ether, , alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitester, lignin, sulfite waste liquor and methyl cellulose.

Powders, emulsifiers and powders can be prepared by mixing or co-grinding the active substances with a solid carrier.

16 14432 1

Granules, e.g. envelope, impregnation and homogeneous granules can be prepared by bonding the active substances to solid carriers. loaded carriers are, for example, mineral soils, such as silica gel, silicas, silica gels, silicates, talc, kaolin, aggregates, limestone, lime, chalk, talc, bolus, loose, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, finely divided fertilizers, such as e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and vegetable products, such as camel, tree bark, wood and nut shell flour, cellulose powder and other solid carriers.

The agents preferably contain between 0.1 and 95% by weight of active substance, especially between 0.5 and 90% by weight.

To the blends or individual active substances can be added oils of various types, wetting and adhesive agents, herbicides, fungicides, nematodicides, insecticides, bactericides, trace elements, fertilizers, antifoam agents (eg silicones), growth regulators, antidotes or other herbicides. active compounds, the option also only immediately before use (tank mix).

The herbicidal compounds may also be used before or after the individual active ingredients included in the herbicide of the invention, or the mixtures thereof.

The mixture of these agents for the herbicide of the invention can be made in a weight ratio of 1:10 - 10: 1.

The amount of herbicide used according to the invention depends mainly on the nature of the desired effect.

The amount of the herbicide used according to the invention is generally between 0.1 and 15 or more, preferably between 0.2 and 6 kg of active substance per day. ha.

The novel agents can be used in cereal cultures and in cultures of dicotyledons.

The new agents exhibit a strong herbicidal effect and can therefore be used as herbicides or to control undesired plant growth. Whether the new agents act as total or selective agents depends mainly on the amount of active substance per day. unit area.

Weed or unwanted plant growth means all monocotyledonous and dicotyledonous plants that grow in places where they are not desired.

EXAMPLE 9 In a greenhouse, cotton (Gossypium hirsutum) was treated in which «as a weed grew a dense stock of arable mustard (Sinapis arvensis), at a height of 2 to 10 cm with the following active substances: 1-ethoxycarbonyl-3-isopropyl 2,1,3-benzothiadiazine (4) one-2,2-dioxide II 1-isobutanesulfonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide III 1-ethanesulfonyl-3-isopropyl-2 , 1,3-benzothiadiazine (4) one-2,2-dioxide IV 1-diethylcarbamoyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide

The amount used in each case was 1 kg of active substance / ha.

The active substances were in each case dispersed or emulsified in 500 liters of water per day. ha.

After 2-3 weeks, compounds I - IV were found to exhibit better compatibility with the culture plants than XIV 3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxide.

The test result is shown in the following table:

Active substance I II III IY XIY

Utility Plants;

Gossypium hirsutum 0 0 0 10 30 Unwanted plants:

Sinapis aryensis 100 100 100 100 100 0 = without damage 100 = total damage

EXAMPLE 1Q

In a greenhouse, various test plants were treated at a height of between 2 and 25 cm with the following active substances: 1-ethoxycarbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) on-2.2-dioxide II 1-isobutanesulfonyl 3-Isopropyl-2,1,3-benzothiadiazine (4) - one-2,2-dioxide III 1-Ethanesulfonyl-3-isopropyl-2,1,3-benzo thiadiazine (4) one-2.2-dioxide IY 1- diethylcarbamoyl-3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide Y1-dimethylcarbamoyl-3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide dioxide YI 1-N-methyl-Nn-propoxymethylcarbamoyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide YII 1-dimethylthiocarbamoyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide YIII 1-β-naphthalenesulfonyl-3-isopropyl-2,1,3-benzothiadiazine- (4) one-2,2-dioxide ΙΣ 1-isopropylaminosulfonyl-3-isopropyl-2, 1,3-benzothiadiazine (4) one-2,2-dioxide X 1-methylaminosulfonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide XI 1- ( 2,4,4,6 '-' (trinitroplienyl) -3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide XIII-me thoxycarbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2.2-dioxide XIII 1-phenoxycarbonyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2.2-dioxide

The amount used was 4 kg of active substance / ha. The active substances were in each case dispersed or emulsified in 500 l water / ha.

After 2-3 weeks, it was found that the active substances showed very good compatibility with the plants and a good herbicidal effect.

The test results are shown in the following table:

Active substance I II III IV V VI VII VIII IX X XI XII XIII

Utility Plants:

Oryza sativa 00000000 00000 G-lycin max. 0000000 0 00000

Sorghum bicolor 00000000 00000

Zea mays 00000000 00000

Triticum aestivum 00000000 00000

Hordeum vulgare 00000000 00000

Secale cereal 000000100 00000

Solanum tuberosum 00000000 00000 Unwanted plants;

Sinapis arvensis 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cyperus esculentus 80 75 75 90 100 85 90 95 80 90 75 100 70 0 = without damage 100 = total damage 144321 20 EXAMPLE 11 In a greenhouse, experimental pots were filled with clay-containing sandy soil and sown with the seeds of rice (Oryza sativa), wheat (Triticum aestivum) and mustard (Sinapis arvensis). Immediately thereafter, treatment was followed with the active substances: IY 1-diethylcarbamoyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide and XII 1-methoxycarbonyl-3-isopropyl-2.1 3-benzothiadiazine (4) on-2,2-dioxide

The amount used in each case was 3 kg of active substance / ha.

The active substances were in each case dispersed or emulsified in 500 liters of water per day. ha.

After 4-5 weeks it was found that the active substances IY and XII showed excellent compatibility with the culture plants and a good herbicidal effect.

The test result is shown in the following table:

Active substance IY XII

Utility Plants:

Oryza sativa 0 0

Triticum aestivum 0 0 Unwanted plants:

Sinapis arvensis 90 90 0 = without damage 100 = total damage 21 144321 EXAMPLE 12

90 parts by weight of the compound of Example 1 are mixed with 10 parts by weight of N-methyl-alpha-pyrrolidone and a solution suitable for use in very small droplets is obtained.

EXAMPLE 13 20 parts by weight of the compound of Example 3 are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the preparation product of 8-10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanol amide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the additive product of 40 moles of ethylene oxide to 1 mole of castor oil. The mixture contains 20 per cent. active substance. With pouring and fine distribution of the solution in water, a spray liquid is obtained.

EXAMPLE 14 20 parts by weight of the compound of Example 3 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the product of 7 moles of ethylene oxide to 1 mole of isooctylphenol and 10 parts by weight of the product of 40 moles of ethylene oxide to 1 mole of castor oil. .

EXAMPLE 15 20 parts by weight of the compound of Example 4 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction of boiling point 210-280 ° C and 10 parts by weight of the preparation product of 40 moles of ethylene oxide to 1 mole of castor oil.

EXAMPLE 16 20 parts by weight of the active substance of Example 5 are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 144 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.

EXAMPLE 17 3 parts by weight of the compound of Example 6 are thoroughly mixed with 97 parts by weight of finely divided kaolin. In this way, a powder containing 3% by weight of the active substance is obtained.

EXAMPLE 38 30 parts by weight of the compound of Example 6 is mixed grimly with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. In this way, a preparation of the active substance with good adhesiveness is obtained.

EXAMPLE 19 In a greenhouse, various plants were treated at a height of between 2 and 18 cm with the following active substances: I 1-phenoxyacetyl-3-isopropyl-2,1,3-benzo thiadiazine (4) on-2.2-dioxide II 1 -p-chlorophenoxyacetyl-3-isopropyl-2,1,3-benzothiadiazine- (4) one-2,2-dioxide III 1-2 ', 4'-dichlorophenoxyacetyl-3-isopropyl-2,1,3-benzo thiadiazine (4) one-2,2-dioxide V 1-α- (2 ', 4'-dichlorophenoxy) propionyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide VII 1-ehloroacetyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide VIII 1-acetoxyacetyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide IX 1-propionyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide X 1-oc-chloropropionyl-3-isopropyl-2,1,3-benzothiadiazine (4) -one 2,2-dioxide XI 1-a-bromobutyryl-3-isopropyl-2,1,3-benzothiadiazine (4) -one-2,2-dioxide XII 1-sec.-valeryl-3-isopropyl-2,1 , 3-benzothiadiazine (4) one-2,2-dioxide XIII 1-0,0-dimethyl-thiophosphoryl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide XIV 1 -0,0-diethyl-thiophospho Ryl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide XV oxalyl-bis-1- [3-isopropyl-2,1,3-benzothiadiazine (4) one-2 2-Dioxide] XVI 1-palmityl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide XVII 1-formyl-3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-di oxide ,. in each case dispersed or emulsified in 500 l water per ha.

Pen used amount in each case 2 kg of active substance / ha.

After 2-3 weeks, it was found that the active substances exhibited a good herbicidal effect with excellent compatibility with the culture plants.

14432 1 24

The test result is shown in the following table:

Active substance I II III V VII VIII IX X

kg / ha 222 22 2 22

Utility Plants:

Triticum aestivum 000 00 0 00

Hordeum vulgare 000 00 0 00

Secale cereal 000 00 0 00

Oryza sativa 000 00 0 00

Glycine max 000 00 0 00 Unwanted plants:

Sinapls arvensis 95 100 90 95 100 100 90 95 0 = without damage 100 = total damage

Active substance XI XII XIII XIV XV XVI XVII

kg / ha 2 2 2 2 2 2 2

Utility Plants:

Iriticum aestivum .0 0 0 0 0 0 0

Hordeum vulgare 0 0 0 0 0 0 0

Secale cereal 000 0000

Oryza sativa 0 0 0 0 0 0 0

Glycine max 0 0 0 0 0 0 0 Unwanted plants:

Sinapis arvensis 95 100 100 95 90 90 90 0 = without damage 100 = total damage 14432 1 25 EXAMPLE · 20 In a greenhouse, experimental herb pots were filled with clay-containing sandy soil and seeded with various seeds. Immediately thereafter, treatment was carried out with the active substances II 1-p-chlorophenoxyacetyl-3-isopropyl-2,1,3-benzothiadiazine-X4) one-2,2-dioxide III 1-21,4'-dichlorophenoxyacetyl-3-isopropyl -2,1,3-benzothiadiazine (4) one-2,2-dioxide IV 1-2 * -methyl-4'-chlorophenoxyacetyl-3-isopropyl-2,1,3-benzothiadiazine (4) one -2,2-dioxide V 1-05- (21,4'-dichlorophenony) propionyl-3-isopropyl-2,1,1-benzothiadiazine (4) one-2,2-dioxide VIII 1-acetoxyacetyl-3- isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide IX 1-propionyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide X 1-α chloropropionyl-3-isopropyl-2,1,3-benzothiadiazine (4) - one-2,2-dioxide, XIII 1- 0,0-dimethyl-thiophosphoryl-3-isopropyl-2,1,3-benzothiadiazine ( 4) on-2,2-dioxide XIV 1- 0,0-diethyl-thiophosphoryl-3-isopropyl-2,1,3-benzothiadiazine (4) on-2,2-dioxide in each case dispersed or emulsified in 500 l water per ha.

The amount used in each case was 3 kg of active substance / ha.

After 4-5 weeks it was found that the active substances showed a good herbicidal effect with excellent compatibility with the culture plants.

26 1Λ Λ 3 2 1

The test results are shown in the following table:

Active substance II III IV V VIII IX X XIII XIV

kg of active substance / ha 3 3 333 333 3

Utility Plants:

Zea mays 00 000 000 0

Iriticum aestivum 00 000 00 0 0

Oryza sativa 00 00 0 000 0

Glycine max. 0 0 000 00 0 0

Gossypium hirsutum 00 000 000 0 Unwanted plants:

Sinapis arvensis 100 95 95 100 80 90 80 80 100 0 = without damage 100 = total damage Example 21 In a greenhouse, various plants were treated at a growth height of between 2 and 10 cm with the following active substances: VII 1-ehloroacetyl-3-isopropyl -2,1,3-benzothiadiazine (4) one-2.2-dioxide VIII 1-acetoxyacetyl-3-isopropyl-2,1,3-benzothiadiazine (4) one-2.2-dioxide X1-oc-chloropropionyl -isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide XIII 1-0,0-dimethyl-thiophosphoryl-3-isopropyl-2,1,3-benzothiadiazine (4; one-2, 2-dioxide 1 Comparison with the known active ingredient ZIX 3-isopropy 1-2,1,3-benzothiadiazine (4) OI-2,2-dioxide, in each case dispersed or emulsified in 500 l of water per day. ha.

144321 27

The amount used was 1 kg of active substance / ha in the culture plant and 0.8 kg of active substance / ha in the unwanted plants.

After 2-3 weeks, it was found that the active substances VII, VIII, X and XIII with 1 kg of active substance / ha showed a better compatibility with the culture plant and with 0.8 kg of active substance / ha showed an equally good herbicide action against the undesirable plants in comparison with the active substance XIX.

The results of the investigation are shown in the following table:

Active substance VII VIII X XIII XIX

kg / ha 0.8 1 0.8 1 0.8 1 0.8 1 0.8 1

Utility Plant; G-ossypium hirsutum - 0 - 10 - 0 - 0 0 30 Unwanted plants:

Sinapis arvensis 100 - 95 - 95 - 100 - 95 -

Matricaria chamomilla 100 - 96 - 95 - 100 - 95 - 0 = without damage 100 = total damage EXAMPLE 22 In a greenhouse, various plants were treated at a growth height of between 5 and 15 cm with the following active substances: A 1-sec-valeryl -3-isopropyl-2,1,3-benzothiadiazine (4) one-2,2-dioxide B 1-phenoxy-carbonyl-3-isopropyl-2,1,3-b enzothiadiazine (4) one-2,2-dioxide C 1- [N-methyl-benzimidyl] -3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide at 2.0 kg / ha, in each case dispersed or emulsified in 500 l of water / ha. During the trial, 20 mm of precipitation was obtained with the exception of Zea mays, which obtained 60 mm, and Glycine max, which received 180 mm.

After 3-4 weeks it was found that the active substances A, B, C showed good compatibility with Zea mays, a still reasonable damage to Gossypium hirsutum and a strong herbicidal effect on Bidens pilosa and Chrysanthemum segetum. Compound A also showed a good herbicidal effect on Anthemis nobilis, while Compounds B and C showed a poorer effect.

The example confirms that one can control broadleaf weeds in cultures of Gramineae and soybeans (Glycine max.).

The test results are shown in the following table:

Active substance A B 0 kg / ha 2.0 2.0 2.0

Utility Plants:

Glycine max. 10 (3) 15 (2) 20 (1)

Zea mays 6.6 (3) 10 (2) 0 (1) Unwanted plants:

Anthemis nobilis 95 (1) 60 (1) 40 (1)

Bidens pilosa 90 (1) 95 (1) 95 (1)

Chrysanthemum segetum 95 (1) 95 (1) 95 (1) () = number of trials; at several trials average values.

EXAMPLE 25 In a greenhouse various plants were treated at a growth height of 10 - 17 cm with the following active ingredient: A 1- [N-methyl-benzimidyl] -3-isopropyl-2,1,3-benzothiadiazine-4 on-2.2-dioxide at 1.0 kg / ha, emulsified in 500 l of water per ha.

During the trial, Oryza sativa yielded 280 - 300 mm of rainfall and Ammania coccinea 50 - 60 mm of rainfall.

After 3-4 weeks, it was found that the active substance C exhibited a strong herbicidal effect with good compatibility with the culture plant.

The example refers to the fact that compound 0 can combat sump and water weeds in rice fields.

The test result is shown in the following table:

Active substance C

kg / ha 1.5

Utility Plants:

Oryza sativa 5 (2) Unwanted plants:

Ammania coccinea 97j5 (2) () = number of trials; at several trials average value.

EXAMPLE · 24 Outdoor plants treated different plants at a height of between 2 and 14 cm with the following active substances: 30 144321 hv®3 ^ Λη ^ ° 2 -½¾

o ~ b-olQ

a? . H .ΛΗ, \ N ~ EC ^ nA “> '^ ch3 s = c-n <; -3 1 H ^ CH 3 SO 2 -NH-CH 2 * <2: JN / ^ ° C * n ^ ch 3 with in each case 3.0 kg / ha and in addition in each case 2 1 wetting agent / ha, in each case cases dispersed or emulsified in 500 l water per ha. During the trial, 20 - 30 mm of precipitation was given.

After 3-4 weeks it was found that the compounds B, B, E, E were opposite to them. dicotyle weeds Chenopodium album, Galinsoga parviflora, Galium aparine, Matricaria ehamomilla, Polygonum persi-caria, Sinapis arvensis and Stellaria media showed a good to excellent herbicidal effect. Amaranthus retroflexus was also well controlled by substances B, D, E, while substance E exhibited a poorer effect. The plant Oryza sativa "is only slightly damaged by compounds B, D, E and E.

The results of the investigation are shown in the following table:

As the wetting agent, the adhesive product of 6-7 moles of ethylene oxide was used to 1 mole of isooctylpbenol.

Humidify Humidify Humidify Humidify Humidify

Active substance average mean average kg / ha 3.0 + 2.0 3.0 + 2.0 3.0 + 2.0 3.0 + 2.0

Utility Plants:

Oryza sativa 5555 Unwanted plants:

Amaranthus retroflexus 100 80 95 65

Chenopodium album 100 100 100 100

Galinsoga parviflora 100 100 100 100

Galium aparine 100 80 100 90

Matricaria cbamomilla 100 100 100 ---

Polygonum persicaria 90 100 100 100

Sinapis arvensis 100 100 100 100

Stellaria media 100 80 100 100

With the listed compounds, it is possible to successfully fight ground weed. In the experiments, rice was used as a representative of Gramineae cultures, which is why the compounds listed seemed suitable as herbicides.

EXAMPLE 25 Outdoor plants treated different plants at a height of 2 - 10 cm with the following active substances: 52 U4321 0 CU * 'tt H / ^ 0 = C -OCgH ^ in h / cB?

E

^ 02 ^ o £ ch2-ch.cH_ jL h / 0¾ L [^^> - <0 ^

UiA ^ SO2 SOp -

: XO

with in each case 1.5 kg / ha and further in each case with 2 1 wetting agent / ha, in each case dispersed or emulsified in 500 1 water per hectare. ha. During the duration of the experiment, 9 - 11 mm of precipitation fell.

After 3-4 weeks, it was found that the active substances I, K, I showed a strong herbicidal activity against dicotyledonous plants such as Centaurea cyanus, Chenopodium album, Sinapis arvensis, Stellaria media, Spergula arvensis, while Amaranthus retroflexus and Polygonum persicaria did not respond as much to the treatments. Compounds I and 1 were found to be fully compatible with Glycine max, while substance X against Glycine max caused poor etching and growth inhibition.

The test result is shown in the following table.

33 144321

Humidify- Humidify- Humidify-

Active Fertilizer Fertilizer kg / ha 1.5 + 2.0 1.5 + 2.0 1.5 + 2.0

Utility Plants:

Glycine max 0 10 0 Unwanted plants:

Amaranthus retroflexus 70 40 30

Centaurea cyanus 100 100 100

Chenopodium album 100 100 100

Polygonum persicaria 0 0 60

Sinapis arvensis 100 90 90

Stellaria media 100 100 80

Spergula arvensis 100 100 80 EXAMPLE · 26 In the open field various plants were treated at a height of between 2 and 10 cm with the following active substances l 5 / 0¾, .CH 2 OC-Ε, η 0 = CN <T * 1 CH ^

Ϊ H ^ - “S.

G

5 / 0¾ 0 = C-N ^? ^ CH, 14432 1 9 H ^ CH, „N-CCT ^. SOg-NH-Cjtt ^ i 0 ί H ^ CH, Μ N-Cv ^ υ;> 2>, O = C-0-CHj O.V ??

0 = C-N <T J

C2H5 with in each case 1.0 kg / ha, in each case dispersed or emulsified in 500 l water. per. ha. 1.0 kg of ammonium polyacrylate was added to the spray liquid. ha to achieve an improvement in the distribution of the active substance on the leaf surfaces. During the duration of the experiment, 10-20 mm of precipitation fell.

After 3-4 weeks, it was determined that the unwanted plants Chenopodium album, Galinsoga parviflora, Matricaria ehamomilla, Sinapis arvensis, Stellaria media were well controlled to excellent with the compounds P, G, Η. M. Amaranthus retroflexus is also well combated with the drug M. In addition, the substance N showed an excellent effect on Amaranthus retroflexus, Chenopodium album, Stellaria media, while the effect on Galinsoga parviflora and Sinapis arvensis was less strong. Amaranthus retroflexus was not or hardly damaged by the substances P, G, Ξ. The pore compound P was found to be compatible with soybeans (Glycine max). Substance H showed a slight and product G a slight damage to soybeans, while soybeans were more severely damaged by compounds M and N.

The test result is shown in the following table.

Active substance F G Η Μ N

kg / ha 1.0 1.0 1.0 1.0 1.0

Utility Plants:

Glycine max 0 20 10 45 25 Unwanted plants:

Amaranthus retroflexus 0 20 0 100 100

Chenopodium album 90 100 95 100 100

Galinsoga parviflora 100 100 90 100 65

Matricaria chamomilla 100 --- 100 100 ---

Sinapis arvensis 85 80 90 90 75

Stellaria media 100 100 100 100 100 0 = without damage 100 = total damage

The present example suggests that broadleaf weeds can be combated with the listed substances and as a culture plant for the substances F, H, G, soybeans (Glycine max) are useful. However, in this present form, this culture is only considered to a lesser extent in connection with the compounds N, especially M, due to the enhanced damage effect.

Claims (1)

Herbicide, which contains as active ingredient a substituted 2,1,1-benzothiadiazine (4) on-2,2-dioxide, preferably in an amount between 0.1 and 95% by weight of the herbicide, characterized in that it substituted 2,1,1-benzothiadiazine (4) on-2,2-dioxide has the formula: \ VHC - c <3 12 K? wherein R is (a) a formyl group, a propionyl, sec.-valeryl, pelargonyl or palmityl group, a halo atom or acetoxy group substituted with 2-4 carbon atoms, an optionally in the phenyl ring halogen and / or alkyl group. substituted phenoxyacetyl or propionyl group, a 3-pentenoyl group or an oxalyl group the other bond of which is linked to yet another group of the above formula, or (b) an alkoxy or alkyl mercaptocarbonyl group, a phenoxy carbonyl group or a p-chlorobenzyl mercaptocarbonyl group, or (c) an optionally substituted alkoxy group dialkyl carbamoyl group, a dialkylthiocarbamoyl group, an N-phenyl-N *, N'-dialkylformamidinyl group or (d) an alkanesulfonyl group or an optionally substituted halogen or an or (e) a monoalkylsulfamoyl group or