DE1468220B - Selective herbicides - Google Patents

Description

The present invention relates to selective herbicides Agent, characterized by a content of sulfonylcarbamic acid esters the general formula

Y — 4> —S0 ₂ —NH — C— OCH ₃ (I)

in which Y denotes the nitro, amino, methoxycarbonylamino, methylamino or N-methylformylamino group, or their alkali, ammonium or amine salts.

The herbicidal agents contain one or more of the sulfonylcarbamic acid esters listed above together with at least one compatible solid or liquid diluent or one compatible mineral, animal or vegetable oil for use in herbicidal compositions is suitable, preferably together with wetting, dispersing or emulsifying agents. Preferably the compositions contain from 0.05 to 50 percent by weight sulfonyl carbamic acid ester.

Examples of suitable solid diluents are talc, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, absorption carbon black, a clay such as kaolin or bentonite, or a compatible one solid wetting or dispersing agent. The solid compositions that take the form of dusts, Granules or wettable powders are preferably prepared by using the sulfonylcarbamic acid esters according to formula (I) ground with the solid diluents or by the solid diluent with solutions of the sulfonylcarbamic acid esters in volatile solvents are impregnated, whereupon the solvents evaporate and, if necessary, the products to powder to be married. Granular formulations can be prepared by using the volatile Sulfonylcarbamic acid ester dissolved in solvents is absorbed by the granular diluents and the solvents are evaporated or by adding compositions as described above obtained in powder form can be granulated. The wetting, dispersing and emulsifying agents, which are preferably present in wettable powders in particular, can be of the ionic or be nonionic type, for example sulforicinoleates, quaternary ammonium derivatives or on condensates made up of ethylene oxide products such. B. Condensates of ethylene oxide with octylphenol, or fatty acid esters of anhydrosorbitol compounds, which are obtained by etherification of the free hydroxyl groups made soluble by condensation with ethylene oxide. It is preferred to use agents of the non-ionic type as this over against Electrolytes are not sensitive. Wettable powders according to the invention can with water directly converted into ready-to-use emulsions or suspensions before use.

Liquid compositions according to the invention normally take the form of solutions, suspensions or emulsions from the sulfonylcarbamic acid esters and contain a wetting, dispersing or emulsifiers. These emulsions and solutions are prepared from aqueous, organic or aqueous-organic media, such as. B. acetophenone, isophorone, Toluene or xylene or mineral, animal or vegetable oils or mixtures of these Diluents which are wetting, dispersing or emulsifying agents of the ionic or nonionic type, for example those of the types described above. As with the solid compositions wetting, dispersing and emulsifying agents of the nonionic type are preferred, since these are not sensitive to the presence of electrolytes. If desired, the emulsions can the sulfonylcarbamic acid ester in the form of self-emulsifying concentrates, which the active Substances in the emulsifiers or in solvents that contain emulsifiers that interact with the Active ingredients are compatible, can be used, from which ready-to-use by simply adding water Funds are obtained.

Herbicidal agents in the form of aerosols containing one or more of the carbamic acid esters according to formula I also fall within the scope of the invention. All of the above Compositions can furthermore contain binders or other customary additives.

The herbicidal agents can also contain other herbicidally active compounds, such as. B. MCPB [y - (4 - chloro - 2 - methylphenoxy) - butyric acid], 2,4-DB [y - (2,4 - dichlorophenoxy) - butyric acid], MCPA (4-chloro-2-methylphenoxy-acetic acid) , 2,4-D (2,4-dichloro-phenoxyacetic acid), 2,4,5-T (2,4,5-trichlorophenoxyacetic acid), phenylcarbamates and ureas, for example propham (isopropyl-N-phenylcarb * amate) and chlorpropham [Isopropyl-N- (3-chlorophenyl) - carbamate] and dalapon (sodium - a, a - dichloropropionate) contain.

The herbicidal compositions according to the invention can be used both before germination and after germination of weeds, such as B. Wild oats (Avena fatua), perennial winter newt (Lolium perenne), Echinochloa (Echinochloa crusgalli), green foxtail (Setaria viridis), sour grass (Digitaria sanguinalis), Foxtail (Alopecurus pratensis), dog chamomile (Matricaria inodora), corn marigold (Chrysanthemum segetum), common ragwort (Senecio vulgaris), black bindweed (Polygonum convolvulus), Red foot (Polygonum persicaria), couch grass (Agropyron repens), creeping ostrich grass (Agrostis stolonifera), Sedum plant (Chenopodium album), dock (Rumex sp.), Annual bluegrass (Poa annua), field mustard (Sinapis arvensis), goose grass (Eleusine indica), annual pig thistle (Sonchus sp.), creeping thistle (Cir-

sium arvensis) and Amaranthus sp. in plantings, a formula

like ζ. Β. Onion, radish, rape, mustard, cress, beet, Alfalfa, clover, broad beans, French beans, peas, lentils, carrots, sunflowers, potatoes, tomatoes, Linen, cabbage, soybeans, peanuts, cotton, can be used without causing any substantial damage of the plantings at the dosages normally required to control the weeds occurs.

The compositions can also be used to control weeds, such as couch grass, in fallow land or uncultivated land, d. H. Land on which no planting grows can be used. The necessary Dosages and the type and time of application vary depending on the type of control to be controlled Plant or plants, the planting and the desired effect. Generally surrendered in consideration of these factors, dosages of active material between 0.454 and 4.54 kg per 0.40 hectare good results.

Those agents which contain methyl p-aminobenzene sulfonyl carbamate are of outstanding importance and contain methyl-ρ-nitrobenzene-sulfonylcarbamate because they are particularly valuable for combating of wild oats, couch grass, green foxtail, ostrich grass, goose grass, foxtail, annual Bluegrass, chamomile, Polygonum sp., Ragwort, Dock, field mustard, annual pork thistle, sourgrass and corn marigold in sugar beet, Linen, peas, alfalfa, cotton, soybeans, potatoes, tomatoes and cabbage when applied germination as well as to combat the germination of wild oats, foxtail, annual Bluegrass, sedum plant, chamomile and Polygonum sp. with peas, broad beans, welsh Beans and soybeans are. Compositions containing methyl p-methoxycarbonylamino-benzenesulfonylcarbamate are particularly valuable for combating after the germination of sourgrass in Cotton.

Active ingredients in which the substituent Y is the methylamino group or the N-methylformylamino group means are suitable for controlling weeds, such as wild oats (Avena fatua), annual bluegrass (Poa annua), foxtail (Alopecurus pratensis), couch grass (Agropyron repens), field mustard (Sinapis arvensis), dog chamomile (Matricaria inodora) and Polygonum sp. in plantings such as peas, beans and lentils, before or after germination, without substantial damage to the plantings at the dosages normally required to destroy the weeds occurs.

The sulfonylcarbamic acid esters of the general formula can be used per se for the preparation of Sulfonyl carbamates known processes are produced. Typical methods by which the invention Active ingredients can be produced are summarized below. In the following Formula Y has the meanings given above.

CH ₃ OCOCl

in an aqueous or organic medium in the presence of a basic condensing agent, preferably at a temperature between 10 and 20 ^0C in aqueous media at reflux temperature and in organic media.

(b) Reaction of an isocyanate of the general formula

SO ₇ NCO

with methanol, the reaction, which is exothermic, preferably being carried out at a temperature between 50 and 100 ^° C. in a solvent such as a chlorinated aromatic hydrocarbon of high boiling point, for example trichlorobenzene, in the presence of a slight excess of methanol.

(c) Reaction of a sulfonyl halide of the general formula '.

SO ₂ shark

wherein Hal is a halogen atom, preferably a chlorine atom, with a carbamate of Formula. ;

NH ₇ COOCH,

the reaction being carried out in an organic solvent at reflux temperature in the presence a basic condensing agent, e.g. B. a tertiary amine, preferably pyridine. or an alkali derivative, e.g. B. potassium carbonate, or on the other hand and preferably the starting material carbamate of the above formula in the form of a Alkali, in particular a sodium derivative, is present. , ■ ·: ■

(d) transesterification of an ester of the formula

SO ₇ -NH-C-OR

with methanol.

(e) Implementation of a urea derivative of the general formula

(a) Implementation of a sulfonamide derivative of the general formula ■.

with a chlorocarbonic acid derivative of the general form R ₁ . and R _{2 can be the} same or different and are hydrogen atoms ■ or ··· lower alkyl groups. mean, with methanol at elevated temperature, preferably in an excess of the methanol as solvent, usually under pressure and in the presence of an acid catalyst, such as. B. sulfuric acid.

5 6

(0 Oxidation of a sulphenyl or sulphinyl compound (1) If the sulfonyl carbamic acid ester is required of the general formula mel I is in the form of an amine salt, treatment the compound of formula I with a

YJ / ^ -A NHCOOCH stoichiometric amount of the amine which

\ - / ³ 5 for example from diethanolamine, triethan oil

. λ · ο j ο / λ / - ujii -ι amine, octylamine or morpholine can exist,

wherein A is an S or SO group, with '· ^: ■ ■:. ··. · ...

for example hydrogen peroxide in a (m) If the sulfonylcarbamic acid ester of the formula

Solvent, such as acetone, acetic acid or a mel I in the form of an ammonium salt,

Mixture of acetic acid and acetic anhydride, treatment of a solution of the. Connection of

if desired at elevated temperature, for example formula I in a solvent, such as ' j .. B. Metha-

about 100 ⁰ C. ■ nol, with gaseous ammonia ;. · ..; ■; ■

(g) If Y is a primary amino or N-methyl- 'Example 1.

amino group means hydrolysis of a - ^: - ^: · '' ■■ · "-""■''

bond of the general formula .15 ^E "i mixture of 48 g vermiculite, 50 g methyl

p-aminobenzene sulfonyl carbamate and 2 g of a

V_cA \ TurnnrH densation product from 10 moles of ethylene oxide and

/ ^iU 2 ^WHLUULH 3 1 mole of octylphenol is finely ground. The get-

■■. "". . ,. . ■ ...,,. ,. tene fine wettable powder becomes after it is in

in which Y an acylamino or N-methyl-low _2o water was suspended, with 1.81 kg of active material

acylamino group, preferably an N-Methy - _{dal applied per Q4Q hectare and gives one to} _

acetamido means, preferably by _RIE f tory control of foxtail and

Treatment with an excess of watery _{wild oats in} sugar beet plantations.
Sodium hydroxide solution at room temperature.

,,. ",,.,. ... .. uj * *. Example2

(h) If Y is a primary amino group, 25 ^v

catalytic hydrogenation of a compound of 100 ecm of a 20% solution in acetone of

general formula methyl p-nitrobenzenesulfonylcarbamate is added dropwise in a ribbon blender on 80 g Attaclay grains

n MHrnnru cast, their diameter between 2 and 5 mm

^U 2 ^1NHLUULH 3 ₃₀ varied. The solvent is immediately after

Adding the solution evaporates by removing the mixture

in a solvent, e.g. B. absolute ethanol, kept at about 30 to 40 ° C and the interior of the

is blown with a stream of air using Raneynickel or Adams apparatus.

Platinum catalyst. The grains will eventually be diminished

... "" _v . . . , Ui- u 35 pressure dried at 40 to 50 ° C.

(1) If Y loading methoxycarbonylamino _{The he} preserved grains before the germination

indicates implementation of a carbamic acid ester used _{with 9fi7 kg of granules per} 0.40 hectare and

general formula result in a satisfactory control of annual

. -. lichen bluegrass, foxtail, stonecrop, dog-

H ₂ N— <ζ y —SO ₂ NHCOOCH ₃ 40 chamomile and wild oats in plantings of wide

\ = / Beans.

with a chlorocarbonic acid ester of the formula Example 3

CH O · COCl ^ ' ^{n emu} lgi ^erDares concentrate is made from

.. ". , '. ,.,,. . ⁴⁵ methyl-p-aminobenzenesulfonyl-

m an aqueous or organic medium in carbamate ■ ■. ■ ^J 20 σ

Presence of a basic condensing _{agent Tween 80} (pöiyoxyiiihiiensörbitan- '

preferably at a temperature between 10 monooleate) jq "

and 20 ⁰ C in aqueous medium or with reverse acetophenone '.'. '.'. '.'. '.'. '.'. '.'. '.'. '.'. '. ad 100 ecm *

nut temperature in organic media. 50 '

... "".,. _XT »,,, r 1 ·, This concentrate is in an amount of 1.36 kg

ü) If Y has an N-methyl-formylamino group _{active Matcria} , _{each 040 hectares according to ejner} ■

indicated by1 formation of the corresponding _Neten dilution with water, for example. B. 1 part concentrate

Compound of the formula I worm Y _{uses a monotetrate to J6 part of water and} results in a

methylamino group means, preferably satisfactory control of wild oats, dog

by using formic acid or formiu _{redfoot and mercury in sugar} beet plant

mylfluond. _tongues

(k) If the sulfonylcarbamic acid ester of Example 4

mel 1 is in the form of an alkali salt, hand. :

development of the compound of the formula with a 60 100 g of methyl p-aminobenzenesulfonyl carbamate

stoichiometric amount of an alkali metal or that with 3 g Texofor FX85 (polyoxyethylene-alkyl-

AlKalimetallalkoxyds or Hydroxyds in a phenol condensate) mixed. It will be distilled

suitable solvent. The water is preferably used up to a total volume of 500 ml

The reaction is carried out by adding the ester, whereupon in a ball mill for 2 hours

I-ormcl I with an alkali metal, preferably (.5 den long milled. The suspension obtained

Sodium, dissolved in an excess of a low, is diluted with water and in an amount of

against aliphatic alcohol such as methanol. 0.9kg of active material per 0.40 hectare of cotton

bchandclt and evaporated to dryness. planting sprayed with goose grass and l-ichino-

7 8

chlba is contaminated. This concentrate is used in an amount of 1.81 kg to control these weeds. active material per 0.40 hectare according to the corresponding. . Dilution with water, for example 1 part of concentrate Example 5 r _au 20 parts of water, used> and results in a to-A sprayable suspension in oil peace for cancellation of methyl 5 control of wild mustard, Hundsp-methoxycarbonylaminobenzolsulfonylcarbamatwird kamillie, wild oats and foxtail in peas produced by the active material in isophorone plants when applied before germination,
is dissolved to a 20% solution, in which 5 weight percent / volume Tween 80 are incorporated. Example 10
2 parts of this concentrate are used with a Trak- 10

tor diesel oil (18 parts) mixed with a wettable powder is thoroughly mixed

oil suspension results, which with an amount of mixing 50 g of methyl-p-N-melhylformyl-

1.81kg of active material per 0.40 hectare of sprayed aminobenzenesulfonyl carbamate, 40 g of kaolin and 10 g

and a satisfactory control of aus- Pentrone T (anionic wetting agent of the type

permanent grasses, such as B. couch grass and ostrich grass, 15 sulfonated alcohol). This powder will

causes. in an amount of 1.81 kg of active material each

η ■ ία 0> 40 hectares after it has become a suitable

ü e 1 s ρ 1 e _neten concentration, _z β 35 kg wettable powder

An emulsifiable concentrate is prepared for every 454 l of water that has been suspended and used

from 20 results in a satisfactory control of arable

.... , ..., mustard, wild oats and foxtail in pea plants

cibarnat ^"1 '" ^ENZ "20 g ^initially ^ ^{s when} applied after germination.
2,4-dichlorophenoxybutyric acid

(Butyl ester) 8g ₂ Example 11

ween 8 A solution is used after germination

Acetophenone ad 100 ecm of _{the sodium salt of} methyl-p-aminobenzene sulfate

This concentrate is mixed with an amount of 1.90 kg of fonyl carbamate in an amount of 2.2 kg of active subactive material (1.36 kg of carbamate, 0.54 kg of 2,4-distance, expressed as benzenesulfonyl carbamate, per chlorophenoxybutyric acid butyl ester) 0.40 hectares each 30 hectares by spraying on flax plants, which after a suitable dilution with water, z. B. Wind oats and knotweed are affected. 1361 solutions per 0.40 hectare are used and a satisfactory control of this problem is obtained. A satisfactory control of wild oats and herbs without noticeable damage to the crop is obtained.
Setaria, annual pig thistle, thistle, sedum plant,
Amaranthus sp. and field mustard in lucerne plantations. 35 examples

B e i s ρ i e 1 7 A solution is used after germination

100 g of methyl-p-methylaminobenzenesulfonylcarb- the potassium salt of methyl-p-nitrobenzenesulfonyl-

amate with 3 g Texofor FX85 (polyoxyethylene carbamate in an amount of 4.4 kg of active substance

alkylphen oil condensate). It is distilled 40 (expressed as benzenesulfonyl carbamate) per hectare.

Add water to a total volume of 500 ml. A satisfactory control of

give, whereupon wind oats and feverfew in potato plantations in a ball mill for 2 hours

will be married for a long time. The suspension obtained is without noticeable damage to the plantings,
ground with water to form a suspension, which

with an amount of 1.81 kg of active material per 45 Example 13
0.40 hectare is sprayed and a satisfactory

Fighting couch grass results. The potassium salt of methyl-p-ami- ■ _ is used. . Nobenzenesulfonyl carbamate in the form of a 0.8% solution (weight per volume) containing 0.8% “TENOFOR A sprayable suspension in oil of methyl 50 FN 11” (commercial product based on a condensate methylaminobenzenesulfonyl carbamate) of ethylene oxide with alkylphenols) provides by adding the active material in isophorone to this solution is dissolved directly between the series of 20 weight percent / volume. Then puts fruit trees in one. Amount of 550 l / ha for Konman 5 weight percent / volume Tween 80 (polytrolls of Echinochloa, Eleusine, fingergrass and oxyethylene sorbitan monooleate. 2 parts of this Konman 55 Setaria species sprayed,
Zentrates are mixed with 18 parts of a tractor diesel oil, resulting in an oily suspension, B is ρ ie 1 14
which with an amount of 1.81 kg of active material

every 0.40 hectare is sprayed and one is satisfied. After germination, an aqueous one is used

causing regulation of the couch grass. 60 solution of the triethanolamine salt of methyl p-meth-

' _B. iQ made oxycarbonylaminobenzenesulfonylcarbamate

. . ^öei game 9 by dissolving methyl-p-methoxycarbonyl-

An emulsifiable concentrate is made in a solution of aminobenzenesulfonyl carbamate

from 1 equivalent of triethanolamine in water) for loading

Methyl-p-methylaminobenzene- 65 spray from through weeds, including finger-

sulfonylcarbamate .. 20 g grass and Echinochloa, impaired young tree

Tween 80 10 g of wool plants in an amount of 2.2 kg of active ingredient

Acetophenone ad 100 ecm (expressed as benzenesulfonyl carbamate) per hectare.

A satisfactory control of these weeds is obtained without any detectable damage to the plants.

Example 15

The mixture of a solution of the potassium salt of methyl p-aminobenzenesulfonyl carbamate is used and the potassium salt of 4-chloro-2-phenoxyacetic acid in an amount of 2.2 kg / ha (expressed as benzenesulfonyl carbamate) or 0.350 kg / ha (expressed as acid). This solution is sprayed on Flax plants, which are caused by wind oats, polygonum species, field mustard, daisy, goose foot, annual grasses and noxious dicotyledons are impaired without noticeable damage to the cultures.

Example 16

A mixture of aqueous solutions of the sodium salt of methyl 4-aminobenzenesulfonyl carbamate is used and the sodium salt of 4- (2,4-dichlorophenoxy) butyric acid in amounts of 2.2 kg of the the first substance (expressed as benzenesulfonyl carbamate) and 1.1 kg of the second substance (expressed as as acid) per hectare of alfalfa. Satisfactory control of grasses such as for example Setaria species, Echinochloa and two-lobed plants such as thistles and dock, with no noticeable damage to the culture.

Example 17

A mixture of an aqueous solution of the ammonium salt of methyl p-nitrobenzenesulfonyl carbamate is used (obtained by reacting methyl p-nitrobenzenesulfonyl carbamate with 1 equivalent of ammonia in dilute solution) and of 3-amino-1,2,4-triazole in an amount of 2.2 kg of the former substance (expressed as benzenesulfonyl carbamate) and 4.4 kg of the second substance per hectare in fallow fields. So one keeps the annual and permanent ones Weeds, such as, for example, Setaria species, couch grass, Echinochloa, fingergrass and the permanent bilobed lobes Plants, Canadian goose thistles, dock and knotweed under control.

Example 18

3. Methyl-pN-methylformylaminobenzölsulfonylcarbamat (mp = 203 to 205 ⁰ C);

4. Methyl p-methylaminobenzenesulfonyl carbamate (M.p. = 132 to 134 ° C);

5. Methyl p-methoxycarbonylaminobenzenesulfonyl carbamate (M.p. = 217 to 219 ⁰ C).

Due to their good solubility in water, the following compounds can be used advantageously:

6. potassium salt of methyl p-aminobenzenesulfonyl carbamate;

7. potassium salt of methyl p-nitrobenzenesulfonyl carbamate;

8. Sodium salt of methyl p-nitrobenzenesulfonyl carbamate;

9. triethanolamine salt of methyl p-nitrobenzenesulfonylcarbamate;

10. Sodium salt of methyl p-aminobenzenesulfonyl carbamate;

11. Sodium salt of methyl p-methoxycarbonylaminobenzenesulfonyl carbamate (M.p. = 258 ° C);

12. Potassium salt of methyl p-methoxycarbonylaminobenzenesulfonyl carbamate.

Test report I

55

20 g of the potassium salt of methyl p-nitrobenzenesulfonyl carbamate are ground and 80 g Ättapulgitton. The mixture is granulated in a conventional manner to give granules with a diameter of 2 to 5 mm receive.

These granules are used in sugar beet fields before germination in an amount of 22 kg / ha. A satisfactory control of bluegrass, wind oats, goosefoot, and feverfew is obtained Polygonum species. A.

The following compounds can be found in the inventions B according to selective herbicidal agents are included: C

1. Methyl p-nitrobenzenesulfonyl carbamate 65D (M.p. = 145 to 148 ° C);

2. Methyl p-aminobenzenesulfonyl carbamate E (M.p. = 145 to 146 ° C);

The benzenesulfonyl carbamates according to the invention are effective against a spectrum of weeds, that differs from the range of known

- Herbicide is different, and it can be applied both before and after weeds emerge will. They are suitable for controlling weeds of the monocot and dicot type after emergence in contrast to (a) other known post-emergence herbicides such as 2,4-dichlorophenoxyacetic acid and 4-chloro-2-methylphenoxyacetic acid, which are not effective against grasses, and too

(b) herbicides such as isopropyl-N-phenylcarbamate and Isopropyl - N - (3 - chlorophenyl) - carbamate (chlorpropham), which are effective against grasses, however generally must be applied before the weeds emerge. The spectrum the weeds to be controlled by the herbicides according to the invention also comprise a number of species previously difficult to control by application to the leaves, such as Avena fatua, Alopecurus myosuroides, Agrostis spp., Holcu?

lanatus, Bromus mollis, Agropyron repens, Polygonum lapathifolium and Rumex crispus. Under these Agrostis, Agropyron and Rumex are perennial plants and therefore particularly annoying in such cases, where plowing is not frequent.

The following tables show the herbicidal activities of the compounds of the invention when applied to the leaves. The designations A to E correspond to the following substances according to the invention:

Methyl p-nitro-benzene sulfonyicarbamate, Methyl p-aminobenzenesulfonyl carbamate, Methyl p-methoxycarbonylaminobenzenesulfonylcarbamate,

Methyl p-N-methylformylaminobenzenesulfonylcarbamate,

Methyl p-methylaminobenzenesulfonyl carbamate.

Table 1

12th

Pllan / ciiurten and growth association

(Number of sheets)

Avena fatua 1 to 2

Agrostis stolonifera 1 to 2

Aurostis tenuis (while skewering)

Aüropyron repens 25.4 to 33.02 cm

high

Alopecurus myosuroides I to 2

Bromus moHis (seedling)

Dactylis glomerata 1 to 2

Hplcus lanatus 1 to 2

Loiium perenne 1 to 2

Poa annua 1 to 2

Dosage of Ilorhicids in units of 1.125 kg, ha, which is necessary for

a) W / o reduction in fresh weight, (b) 70 to "X)% reduction

of fresh weight, (c) 'X)% destruction

(away)

2 1.5 1 0.75 2 0.9 to 1 16 * <16 4th 3 2 0.9 2 1 4th 2 8th 4 to 6 4th 2

as the potassium salt

(al

2 2 4

Chlorprophnm la)

(Continuation)

Plant species and state of growth

(Number of leaves) Dosage of the f Icrbicids in units of 1.125 kg, ha, which is required for

(a) 90% reduction in fresh weight, (b) 70 to 90 "/. igcn reduction

of fresh weight, (c) 90% destruction

as the potassium salt

(C)

as potassium salt (O "

as the potassium salt

(C)

Chlorpmpham Ic)

Polygonum japathifolium 1 bis

Sinapis arvensis 2 to 3

Matricaria inodora 3 to 5

Rumex crispus 15.24 cm in diameter.

2 * 1*

2 to 4*

1.5 *

1*

1*

1 to 2*

about 8 * about 4 * about 8 *

about about

no killing at 8

Applied as a free acid in aqueous acetone solution. Not tested against this species.

table

Plant species state of growth

Minimum effective dose in units of 1.125 kg, ha to achieve 90 to 95% control

as sodium sulphide

A vena fatua

Alopecurus pratensis

Alopecurus myosuroides ......

Poa annua

Polygonum Iapathifolium

Sinapis arvensis

Matricaria inodora:

Holons lanatus

Agrostis stolonifera ..........

Agrostis tennuis .. · .. '

Bromus mollis

Not tested against this species.

Seedling seedling seedling seedling seedling seedling seedling seedling seedling Seedling seedling

4 to 4

2 to 'inactive at 8

4 1

1 2 to

2 2 to

1 to

'

4 1 to

The table below shows those in the ground remaining activity against weeds before

^Run: Table 111

l'flanzenartcn

A vena fatua

Holcus lanata ....

Poa anniia

(henopodium

album

Polygonum

lapathifoüum ...

Sinapis urvensis ...
Matricaria inodora

^: .i necessary Dilsis for 90% igcii Λ htöliing

germinating seeds in units of 1,125 kg ha

i:

<2 <2

Chlorpropharn

<r

<r

* Lowest amount tested

~ Not tested against this species.

Hamlet became plots of potato fields sprayed with aqueous solutions of the compounds to be compared before emergence of the planting, and after 28 days, weed control was determined compared to non-sprayed control plots. The application rate was measured 121 days after the spraying.

The following results were obtained:

Table IV

connection Application
amount in
units
from
1,125 kg / ha Percentage
Combat
of
entire
weed
stock Planting
yield in
units
from
1,125 kg / lia B as the potassium salt
Chlorpropham ..
Not sprayed
Control
parcels 2
2 56
41 6810
5033
6063

Weed species that were found in the control plots that were not sprayed when determining the control, were (the numbers in brackets indicate the number of plants per 0.836 sqm):

Capsella bursa-pastoris (11), Chenopodium album (36),
Cirsium arvense (11),

Convolvulus anensis (12).
Polygonum convolvulus (13), Solatium nigruni (6),
Sonchus arvensis (5),
Sonchus clcraceus (8).

Veronica hederifolia (38).

Vet search report II

. Weed weed raised in pots in the greenhouse

ίο were sprayed with formulas diluted in water of the active ingredients to be examined. In the I-'allc of Avena fatua the number of sprayed plants was 20 to 25, in the case of other species ^ς A corresponding number of plants of each SPCM s

was not sprayed for reasons of comparison. The concentration of the compounds to be examined in the spray liquids were adjusted so that they practically applicable concentrations corresponded to: starting with a minimum of 0.281 kg / ha and

with a geometric factor of 2 to 9.00 kg. ha increasing, with 1901 spray liquid per 0.40 hectare were sprayed. Laboratory precision sprayers were used, which were freshly applied to this Volumes were calibrated.

The spray liquid wedges that contain the potassium salts λ «in Methyl p-N -methylformylaminobenzenesulfonyl cahamate and methyl p-methylaminobenzenesulfonyl aihamate were prepared by dissolving the test compounds in the desired volume of water.

represents, the 0.5 weight percent / volume of a wetting agent with the trade name »Ethylan C P <· were attached. The chlorprophamidal spray liquids were emulsions made by dilution a commercially available liquid composition

setting of 40 percent by weight / volume of chlorpropham, which is known under the name »Farmon CIPC 40«, with water to the desired amount. The addition of 0.5 percent by weight / volume of Eth \ - Ian CP caused the wetting effect of the

containing zolsulfonyl carbamate test compounds Spray liquids. In this way, a comparable adhesion of the spray liquids that the containing three Tesl compounds, on the weed leaves achieved. The plants were subsequently

45.35 days in the greenhouse under standard temperature and -Day length conditions with normal hand watering, starting with the day after spraying, held. The herbicidal activity was determined after 35 days, the amount used being individual

Compound was determined which caused a 90% decrease in growth compared with the untreated plants (ED ₉₀ ). The test results are compiled in the following table:

Plant species

Growing too much when spraying
(Height / number of sheets)

ED «, in units of 1,125 kg / ha

(Potassium salt)

(Potassium salt)

Chlorpropham

Sinapis arvensis -
Matricaria inodora,
Avena fatua

6.35 cm / 3 sheets 2 2 <8

2.54 cm / 6 to 7 sheets> 8 2 NO

15.24 cm / 2 sheets 2 1 4

NR means that no significant herbicidal effect was achieved with the largest dose of test compound used (9.00 kg per hectare)

would.
> 8 means that with the largest dose of test compound used (9.00 kg per hectare) there is about 50% reduction in growth

was achieved.

From the Versuchsberic iten I and II it can be seen that an improved with the substances according to the invention herbicidal activity and better yields can be achieved than with the well-known herbicide Chlorpropham.

Claims (1)

Claim: Selective herbicidal agents, characterized by a content of sulfonylcarbamic acid esters the general formula SO ₂ -NH-C-OCH ₃ in which Y is the nitro, amino, methoxycarbonylamino, methylamino or N-methylformylamino group means, or their alkali, ammonium or amine salts.