FI70224B - TRIALKYLSULFONIUMSALTER AV N-PHOSPHONOMETHYLGLYCIN OCH DERAS ANVAENDNING SOM VAEXTREGULATORER FOER VAEXTER OCH SOM HERBICIDER - Google Patents

Description

70224 Trialkylsulfonium salts of N-phosphonomethylglycine and their use as plant growth regulators and herbicides The present invention relates to novel chemical compounds and their use in the regulation of natural growth or development of plants. In particular, the present invention relates to the chemical treatment of plants when it is desired to alter their natural growth or development in order to increase the various agricultural or horticultural properties of the plants, and also when it is desired to control undesired vegetation.

One skilled in the art of agriculture and horticulture generally knows that the various characteristics of plant growth can be altered or regulated to provide many beneficial effects.

For example, with some types of treatment, leaves can be removed from the plant in a useful manner, i. preventing further growth of plants while allowing the further development of the productive parts of the plant. As a result, the productive parts grow more than normal and subsequent recovery operations are facilitated. Foliage pests are particularly useful on flax, cotton and bean crops and other crops of a similar nature. Although the destruction of the leaves kills the leaves, it is not in itself a hebicidal effect because other parts of the plant are not damaged. In fact, the death of the treated plant is not desirable in an effort to destroy the leaves because the leaves remain attached to the dead plant.

Another effect shown by plant growth regulators is a general slowdown in vegetative growth. This effect has many different useful properties. In some plants, it reduces or eliminates the normal predominant apical growth and thus causes a shorter main stem and increases the formation of side branches. This change in natural growth or development produces smaller, shrub-like plants that often have better resistance to drought and pest damage. Slowing down vegetative growth is particularly desirable in lawn grasses. As the rate of vertical growth of such grasses is reduced, root development increases and a denser, stronger lawn is obtained. Slowing down lawn grasses will also help extend the mowing interval for lawns, golf courses and similar grasslands.

In many different plant types, such as silage fodder plants, potato species, sugar cane, sugar beet, vine species, melons, and fruit trees, slowing vegetative growth increases the carbohydrate content of plants when harvested. Slowing or suppressing such growth at the appropriate stage is believed to result in less carbohydrate being available for available vegetative growth, resulting in higher starch and / or sucrose content. The slowdown in vegetative growth in fruit trees is evidenced by shorter branches and a fuller shape, resulting in easier access to fruit and a simplification of the fruit harvesting process.

U.S. Patent No. 3,799,758 discloses N-phosphonomethylglycine salts useful as herbicides and plant growth regulators, e.g. its alkali, alkaline earth metal and ammonium salts. U.S. Patent No. 3,101,265, on the other hand, discloses that certain sulfonium residues have plant growth regulating activity and lists certain anions with which the sulfonium ion can be combined.

It has now been found that novel trialkylsulfonium salts of N-phosphonomethylglycine are useful both in regulating the natural growth or development of plants and in controlling unwanted growth. These salts of the invention have the formula r3 I o o R2 ~ S l °) n ® ® ° \ | 1 i ^ P- ch2 nhch, coh

R] HCT

II

3 70224 wherein R 1, R 2 and R 3 are the same or different and represent C 1 -C 6 alkyl, and n is zero or one. Preferably R 1, R 2 and R 3 are each C 1 -C 4 alkyl, with up to two of R 1, R 2 or R 3 being the same.

The present invention further relates to a mixture useful as a herbicide or plant growth regulator containing an effective amount of said compounds, and to a herbicidal or method for controlling the natural growth or development of plants comprising applying to the plants an effective, e.g. herbicidally effective, amount of said compounds.

The attached Table V compares three compounds of the present application, namely the trimethylsulfonium, trimethylsulfoxonium and triethylsulfonium salts of N-phosphonomethylglycine, and the two compounds found in U.S. Patent No. 3,799,758, namely N-phosphinium and methyl-calfonic . The table summarizes the results of weed control experiments performed under comparable conditions.

The results show that the compounds of the present invention are clearly more potent than the compounds of said U.S. patent.

As used in the context of the application, the term "natural growth or development" means the normal life cycle of a plant in accordance with its genome and environment, without artificial external influences. One preferred use of the compounds of the invention is to increase the yield of sugar cane and sorghum sucrose grown in the fields. The term "regulation" in this context means the modification or alteration of the normal life cycle by chemical means, temporarily or permanently, without killing the plant.

The term "herbicidally effective amount" means any amount of compounds disclosed herein that kills a plant or any portion thereof. "Plants" means germinating seeds, emerging seedlings and populated 4 70224 vegetation, including roots and above-ground parts. Herbicidal effects include killing, leaf destruction, dry matter, stunted growth, leaf burning, and dwarf growth. Herbicidal effects are generally achieved at higher application rates than growth-regulating effects.

The term "alkyl" is used herein to include both straight and branched chain alkyl groups. The carbon atom region includes its upper and lower limits; for example, methyl, ethyl, n-propyl, isopropyl, butyl, n-butyl, sec-butyl, pentyl, isopentyl, neopentyl, sec-pentyl, hexyl, isohexyl, sec-hexyl and the like. Thus, the term "trisubstituted alkyl" means alkyl substitutions in which the sulfonium cation contains three alkyl groups.

According to the present invention, the control of the natural growth or development of plants is achieved by applying a compound of the above formula or a formulation of such a compound directly to the plants or their above-ground parts about 4-10 weeks before harvest. When applied correctly, the growth-regulating effect can be achieved without herbicidal effects. The amount that constitutes an effective amount will vary not only with the particular material selected for treatment but also with the regulatory effect produced, the species of plant being treated and its stage of development, and whether a permanent or temporary effect is desired. Other factors that affect the determination of that growth regulating amount include the mode of application and weather conditions such as temperature and precipitation. Growth regulation may result from the effect of a compound on either physiological events or plant morphology, or a combination of both, or sequentially. Morphological changes can usually be observed as visible changes in the size, shape, color or structure of the treated plant or any part of it, as well as in the amount of fruit or flowers produced.

Changes in physiological events, on the other hand, occur within the treated plant and are usually invisible to the observer's eye. These types of changes most often occur in the production, location, storage, or use of chemicals that occur naturally in plants, such as hormones. Physiological changes can be observed visually when they are followed by a change in morphology. In addition, many analytical methods are known to those skilled in the art to determine the nature and extent of changes in various physiological events.

The compounds of this invention can regulate the natural growth or development of treated plants in a variety of ways, and it should be noted that not every compound may produce identical regulatory effects in every plant species or at each application rate.

As mentioned above, the reactions vary depending on the compound, application rate, plant, etc.

The herbicidal effects are obtained in a similar manner and the application concentration can be varied to achieve the desired result.

The compounds of this invention are readily prepared from N-phosphonomethylglycine by reacting it with silver oxide to a silver salt or with sodium hydroxide to a sodium salt and treating either the silver or sodium salt with a trialkylsulfonium or sulfoxonium halide. Alternatively, glycine can be reacted directly with a trialkylsulfonium or sulfonium halide in the presence of propylene oxide. N-phosphonomethylglycine is a commercially available substance commonly known as "glyphosate". It can be prepared by phosphonomethylating glycine, reacting ethyl glycinate with formaldehyde and diethyl phosphite <70224, or oxidizing N-phosphinomethylglycine. Such methods are described in U.S. Patent 3,799,758 (Franz, March 26, 1974).

As the examples below show, the compounds of the invention can either regulate the natural growth or development of plants or kill weeds. Although regulatory effects are often desirable as such, the most important thing is often their effect on crop economy. An increase in the yield of individual plants increases the yield per unit area, and the lower costs of harvesting and / or subsequent treatment must all be taken into account when examining the consequences of an individual regulatory effect during growth growth or development.

The following examples are intended only to illustrate in a non-limiting manner the preparation of the compounds of the present invention and their effectiveness in controlling plant growth and controlling unwanted growth.

EXAMPLE 1

Mono-trimethylsulfonium salt of glyphosate

A solution containing 80 ml of tetrahydrofuran and 20 ml of water was prepared. To this solution were added 1.7 g (0.01 mol) of N-phosphonomethylglycine (manufactured by Monsanto Agricultural Products, Co., St. Louis, Missouri) and 0.4 g (0.01 mol) of powdered sodium hydroxide. Then 2.0 g (0.01 mol) of trimethylsulfonyl iodide was added to form a clear solution. The solution was then stripped of volatiles, dispersed in ethanol and heated to 60 ° C. Filtration and drying gave 1.8 g of a white powder, the molecular structure of which was confirmed by C18 and proton NMR spectroscopy to give the mono-trimethylsulfonium salt of N-phosphonomethylglycine. 7 0224 EXAMPLE 2

Mono-trimethylsulfoxonium salt of glyphosate

50 ml of water, 4.2 g (0.025 mol) of N-phosphonomethylglycine and 5.5 g (0.025 mol) of trimethylsulfoxonyl iodide were charged to the reaction vessel. The vessel was gently heated on a water bath and 15 mL of propylene oxide was added. The mixture was stirred for 1 hour, then washed with ether and the phases separated. The aqueous phase was stripped to give 5.8 g of a white powder with a melting point of 184-186 ° C. The molecular structure of the product was confirmed by C13 and proton NMR spectroscopy to the mono-trimethylsulfoxonium salt of N-phosphonomethylglycine.

EXAMPLE 3

The reaction vessel was filled with 100 mL of water, 4.2 g (0.025 moles) of N-phosphonomethylglycine, and 6.2 g (0.025 moles) of triethylsulfonium iodide. The reaction mixture was warmed to 50 ° C and stirred at this temperature for one hour.

It was then cooled to 15 ° C and 15 ml of propylene oxide were added. The resulting mixture was stirred at room temperature for two hours, then washed with ether and the phase separated. The aqueous phase was then separated, redissolved in ethanol, dried over sodium sulfate and washed again with ether. The final yield was 7.5 g of a liquid with a refractive index of n3 ^ 1 =

13 U

1.5197. The molecular structure of the product was determined by C-nuclear magnetic resonance and infrared spectroscopy to be the structure of the monotriethylsulfonium salt of N-phosphonomethylglycine.

70224 EXAMPLE 4 Di-n-butylmethylsulfonium salt of N-phosphonomethylglycine

The reaction vessel was filled with 50 mL of water, 5.1 g (0.03 moles) of N-phosphonomethylglycine, and 8.65 g (0.03 moles) of di-n-butylmethylsulfoxonyl iodide. In addition, 2.2 g (0.0375 moles) of propylene oxide was added to the vessel. The whole reaction mixture was allowed to stand at room temperature overnight. At the end of this time, the reaction mixture was extracted three times with diethyl portions and the phase was separated. The aqueous phase was separated to give a yield of 11.1 g. This product was triturated with tetrahydrofuran (2 x 10 mL), then once with 10 mL of acetone and separated to give 011 g of product. This product was further triturated with 20 ml of acetone followed by 10 ml of diethyl ether and separated. A low melting solid was obtained, yield 9.8 g. The molecular structure of the product was determined by proton nuclear magnetic resonance to give the title compound.

EXAMPLE 5 Diethylmethylsulfonium salt of N-phosphonomethylglycine

In a similar manner to Example 4, 50 ml of water, 6.76 g (0.04 moles) of N-phosphonomethylglycine, 9.3 g (0.04 moles) of diethylmethylsulfoxonyl iodide and 2.9 g (0.05 moles) of propylene oxide were reacted overnight. above room temperature, extracted three times with diethyl ether and the aqueous phase separated from the volatiles (yield 12.3 g). After trituration with acetone and diethyl ether and separation of the volatiles, 12.0 g of the title compound (decomposed at 60-65 ° C) were obtained. The molecular structure of the product was found to be the title compound by proton-nuclear magnetic resonance.

EXAMPLE 6 70224 9 Dimethylisopropylsulfonium salt of N-phosphonomethylglycine

In a similar procedure to Figure 4, 50 ml of water, 6.76 g (0.04 mol) of N-phosphonomethylglycine, 9.3 g (0.04 mol) of dimethylisopropylsulfoxonyl iodide and 3.5 g (0.06 mol) of propylene oxide were reacted overnight at room temperature, extracted twice with diethyl ether and the aqueous phase separated (yield 11.8 g). After trituration with acetone (twice, 10 ml each time), the product was isolated again in a yield of 11.2 g, nj = 1.5232. The molecular structure of the product was found to be the same as that of the title compound by proton magnetic resonance.

EXAMPLE 7 Dimethyl-n-butylsulfonium salt of N-phosphonomethylglycine

In a similar method to Example 4, 50mml was obtained! water: 6.8 g (0.04 moles) of N-osphonomethylglycine, 10.0 g (0.04 moles) of dimethyl-n-butylsulfoxonyl iodide and 3.5 g (0.06 moles) of propylene oxide to react overnight at room temperature, extracted twice with diethyl ether, the phase separated and the volatiles separated (yield 12.4 g). After trituration with acetone (twice, 10 ml each time) and separation, 12.9 g of a hygroscopic white solid were obtained. The molecular structure of the product was found to be the same as the title compound by proton nuclear magnetic resonance.

Other compounds of the general formula described above may be prepared by any of the methods described with suitable starting materials.

EXAMPLE 8 10 70224 This example illustrates the utility of the compound prepared in Example 1 in regulating the growth of sorghum (scientific name: Sorghum vulqare).

The following test method was used:

A number of white plastic pots with a diameter of 19.0 cm were filled with about 4.54 kg of sandy loam containing 100 parts per million (ppm) of cis-N - [(trichloromethyl) -thio] -4-cyclohexene-1, 2-dicarboximide (a commercially available fungicide) and 150 ppm of 17-17-17 fertilizer (i.e. a fertilizer containing 17% by weight of N, 17% by weight of Ρ20% and ^% by weight of K2O).

Eight sorghum seeds were placed in each pot and the pots were placed in a greenhouse maintained at 27 ° C during the day and 21 ° C at night. Over the next five weeks, the emerging plants were thinned to one plant per pot. The pots were fertilized from time to time with 17-17-17 fertilizer.

114 days after seed planting, the plants were sprayed with a solution of the test compound dissolved in equal amounts of acetone and water. The spray device was pressurized with carbon dioxide and mounted on a bicycle-type device. The test solution was sprayed on 750 l per hectare). The concentration of the solution was predetermined so that the application rate, expressed in kg / ha, was obtained as desired when the solution was sprayed on the plants for a total of 750 l per hectare. The concentration was thus chosen to correspond to an application rate of 0.28 kg / ha.

After treatment, the plants were kept in the greenhouse for another 39 days. During this time, the appearance of the seed tip and the shedding of pollen were recorded from time to time.

11 70224

The plants were then harvested. The stems were cut off from the ground and the seed tip and stem were removed. The seed tip was dried from each stem and then the length of the seed stem was weighed and measured. All leaves and leaf sheaths were then removed from the rest of the stem and the length and weight of the stem were determined. The stems were then cut into small pieces and pressed in a hydraulic press at a pressure of 13,800 Nev / ton / cm. The amount of compressed feed was measured, as was its quality in relation to the total amount of dissolved dry matter. The latter was measured with a hand-held refractometer and expressed as a percentage by weight of juice.

Five replicates were made for each application rate. In addition, five untreated plants were included as reference plants for comparison. The results are shown in Tables I and II.

Table I shows data on seed tip emergence and pollen shedding. The figures shown are the averages of each of the five variations. In each case, it is clear that both the amount of seed tip occurrence and the amount of pollen shedding were reduced when the test solutions were applied. This decrease in flowering is one indication of an increase in sucrose formation and storage efficiency.

Table II shows the averages of the measurements for seed tip, seed stalk, stem and pressed juice after plant harvest. The figures show that the weight of the dried seed tip, the length of the seed stalk and the length and weight of the stem decreased compared to the averages of the reference plant.

70224

TABLE I

PRE-CORRECT VALUES Averages of each of the 5 variations (CH3) 3S®0O O (

Test compound: \ I I

^ P CH2NHCH2COH

HO

5 emergence of seed tips (¾) .and pollination shedding (¾) DAYS AFTER SEEDING:

Application 121 131 135 138 149

amount kg / _ha SE SV SE SV SE SV SE SV SE SV

0 (comparison) 0 0 20 7 42 33 74 55 93 93 0.28 0000 0 O 00 00

TABLE II

POST-HARVEST VALUES Averages of each of the 5 variations (ch3i3s®®c> 2 2

Test compound: J J \ jj | ^ P ch2nhch2coh

HO

Application- Dried Seed- Color Compressed juice amount kg / ha seed stalk Height Weight Quantity TDS * weight weight length _ (g) (mm) (mm) (g) (g) (weight0-0) 0 (comparison) 10, 2,234,711 94.5 18.0 13.5 0.28 0.5 20,490 90.2 15.6 13.4 TDS: Total dissolved solids

II

13 70224 EXAMPLE 9 This example demonstrates the post-emergence herbicidal activity of the compounds prepared in Examples 1, 2, 4 and 5.

Aluminum seed boxes measuring 15.2 x 22.9 x 8.9 cm were filled to a depth of 7.6 cm with sandy loam containing 50 parts per million (ppm) of commercial cis-N / (trichloromethyl) thio / -4 -cyclohexene-1,2-dicarboximide fungicide (Captan) and 17-17-17 fertilizers (percentages of N-P 2 O 2 -K 2 O based on dry weight). Several rows were measured across each seed box in the width direction, and different seeds of grass species and broadleaf weed species were planted in the rows, one species per row. The weed species used are shown below:

Broadleaf weeds:

Ipomoea purpurea Xanthium sp.

Datura stramonium Abutilon theophrasti Brassica sp.

Solanum sp.

Amaranthus sp.

grasses;

Cyperus esculentus Bromus tectorum Setaria sp.

Lolium multiflorum Echinochloa crusqalli Sorghum bicolor Avena fatua

Broadleaf species were planted first and grasses were planted 4 days later. Abundant and 70,224 seeds of each species were planted so that a protrusion of 20 to 50 seedlings per row was obtained, depending on the size of each plant.

Ten days after grass planting, emerging seedlings of all species were sprayed with aqueous solutions of test compounds. The solutions were prepared at dilutions such that a spray rate of 750 l / ha indicated 0.56 to 4.48 kg of test compound per hectare according to the needs of each test. Seed boxes that had not been treated at all were used as standards for measuring the amount of weed control in the treated seed boxes.

19 days later, the tested seed boxes were compared to the standard boxes. The weed control percentage of the weeds in each row was estimated to be between 0 and 10 0, with 0% representing the same increase as in the same row of the standard box and 100% representing complete death of all weeds in the row. All types of plant lesions were included in the study. The results are shown in Table III.

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i— x cn-p ra z ο-p ra 70224 EXAMPLE 10 This example demonstrates the subsequent herbicidal activity of the compound prepared in Example 3. The method described in Example 9 was used with the following modifications: Clay species were not included; grass species were sown three days after broadleaf; treatment of the developed seedlings with the test compound was performed eleven days after sowing the carcasses; and injury values were taken 21 days after treatment. The results are shown in Table IV.

Il 17 Table iv 70224 WEED EXTINCTION 5 RESULTS Test compound: N-phosphonomethylglycine, triethylsulfonium salt

Prosenttivertailu_

Application rate kq / ha) Broadleaf_ Grasses_ ABODE__F _H _I__J__K_ _L__M__N_ 0.25 45 50 35 40 65 60 25 45 100 80 75 50 45 0,5 55 65 40 55 80 90 0,5 55 65 40 55 80 90 60 80 100 90 95 100 75 1.0 80 80 55 65 85 95 75 100 100 100 100 100 90 2.0 85 100 65 90 90 100 85 100 100 100 100 100 95 3.0 100 100 90 100 100 100 100 100 100 100 100 100

APPLICATION METHODS

Whether the compounds of the present invention are used as plant growth regulators or herbicides, they are most useful when applied directly to plants after they have protruded from the soil. When used in the field in culture, the compounds are generally in suitable formulations containing other additives and diluent carriers to aid in their dispersion. Examples of such ingredients or carriers are water, organic solvents, dusts, granules, surfactants, water-in-oil and oil-in-water emulsions, wetting agents, dispersants and emulsifiers. The formulations are generally in the form of dusts, solutions, emulsifiable concentrates or wettable powders.

A. DUST

Dusts are dense powder mixtures in which the active compounds are combined with a dense, free-flowing solid carrier. They are intended to be applied dry and designed to settle quickly so that the wind does not transport them to areas where they are not desired.

70 ie 70224

The carrier may be derived from minerals or plants. Preferably, it is an organic or inorganic, high density powder with a low surface area and low liquid absorption capacity. Suitable carriers include mica talc, pyro phytite, dense kaolin clays, tobacco dust and ground calcium phosphate rock.

The performance of the dust can sometimes be improved by adding a liquid or solid wetting agent that is ionic, anionic, or nonionic in nature. Preferred wetting agents include alkylbenzene and alkylnaphthalenesulfonates, sulfated fatty alcohols, amines and acid amides, long chain acid esters of sodium isothionate, esters of sodium sulfosuccinate, ethylene sulfonate and sulfonated fatty acid esters. Dispersants are also useful in these same dust mixtures. Typical dispersants include methylcellulose, polyvinyl alcohol, lignin sulfonates, polymeric alkyl phthalenesulfonates, sodium naphthalenesulfonate, polymethylene bisaphthalenesulfonate, and sodium N-methylacetate acid (N-).

In addition, inert absorbent abrasives are often added to the dust compositions to aid in the manufacture of the dust.

Suitable abrasives include attapulgite clay, diatomaceous silica, synthetic finely divided silica and synthetic calcium and magnesium silicates.

Carriers in typical dust mixtures are usually present in concentrations of about 30 to 90% by weight of the total mixture. The abrasive usually constitutes about 5 to 50 weight percent and the wetting agent up to about 1.0 weight percent. When dispersants are present, they make up about 0.5% by weight of the mixture and may also contain minor amounts of anti-caking agents and antistatic agents. The particle size of the entire mixture is typically about 30 to 50 microns.

B. SOLUTIONS

Aqueous solutions of the active compounds are prepared so as to provide the desired amount of active ingredient in an application rate of from about 9 to about 1875 l / ha. A small amount of non-hytotoxic surfactant is usually present, usually between 0.05 and 0.5% by weight. This improves the wetting ability of the solution and thus its distribution on the surface of the plant. Anionic, cationic, nonionic, ampholytic and zwitterionic surfactants are useful in this regard.

Suitable anionic surfactants include alkali metal, ammonium and amine salts of fatty alcohol sulfates having from 8 to 18 carbon atoms in the fatty chain, and sodium salts of alkyl benzene sulfonates having from 9 to 15 carbon atoms in the alkyl chain. Suitable cationic surfactants are dimethyldialkyl quaternary ammonium halides having from 8 to 18 carbon atoms in the alkyl chains. Suitable nonionic surfactants include polyoxyethylene adducts of fatty alcohols having from 10 to 18 carbon atoms, polyethylene oxide condensates of alkylphenols having from 6 to 12 carbon atoms in the alkyl chains and 5 to 25 moles of ethylene oxide fused to each of the alkylene oxide esters, having 10 to 40 moles of ethylene oxide condensed in each mole of sorbitan ester. Suitable ampholytic surfactants include secondary and tertiary aliphatic amine derivatives in which one aliphatic substituent contains from 8 to 18 carbon atoms and the other substituent contains an anionic water-soluble group such as a sulfate or sulfonate. Examples are sodium 3-dodecylaminopropionate and sodium 3-dodecylaminopropanesulfonate. Suitable zwitterionic surfactants are derivatives of aliphatic quaternary 20 ° 70224 ammonium compounds in which one aliphatic substituent contains 8 to 18 carbon atoms and the other substituent contains an anionic water-soluble group.

Examples are 3- (N, N-dimethyl-N-hexadecylammonio) propane-1-sulfonate and 3- (N, N-dimethyl-N-hexadecylammonio) -2-hydroxypropane-1-sulfonate.

C. EMULSIFIABLE; KONSEfilTRAATIT

Emulsifiable concentrates,; The substances and emulsifiers are dissolved in a water-immiscible solvent. The concentrate is diluted with water before use to form a suspended emulsion of solvent droplets.

Typical solvents used in emulsifiable concentrates include seed oils, chlorinated hydrocarbons and water-immiscible ethers, esters and ketones.

Typical emulsifiers are anionic or nonionic surfactants or mixtures of the two. Examples include long-chain merkaptaanipolyetoksialko-alcohols, alkyy1iaryylipolyetoksialkoholit, sorbitaanirasva-fatty acid esters, polyoxyethylene sorbitan esters with polyoxyethylene glycol esters of fatty or rosin acids, fatty alkyloiiamidikondensaatit, fatty alcohol calcium and amine salts öljyliu-soluble petroleum sulphonates, or preferably of emu LGO in t ia mixtures of i-ne. Such emulsifiers usually comprise about 1 to 10% by weight of the total mixture.

Typical emulsifiable concentrates contain from about 15 to 50% by weight of active ingredient, from about 40 to 80% by weight of solvent and from about 1 to 10% by weight of emulsifier. Other additives such as spreading agents and adhesives may also be added.

D. MOISTURABLE POWDER

Wettable powders are water-dispersible mixtures containing the active substance, an inert solid extender and one or more surfactants, whereby wetting is rapid and no flocculation occurs when suspended in water.

Suitable solid extenders include both natural minerals and materials obtained synthetically from such minerals. Examples are kaolinites, attapulgite clay, montmoron ionic tones, synthetic silicas, synthetic magnesium silicate and also lithium sulphate dihydrate.

Suitable surfactants include both nonionic and anionic types. These surfactants act as wetting agents and dispersants. Usually one such substance is present. Preferred wetting agents include alkylbenzene and alkylnaphthalene sulfonates, sulfated fatty alcohols, amines and acid amides, long chain acid esters of sodium isothionate, esters of sodium sulfosuccinate cetone sulfonate and sulfonated fatty acid esters, sulfated or sulfonated fatty acid esters, oleyl sulphate esters. Preferred dispersants include methylcellulose, polyvinyl alcohol, lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate, polymethylene bisaphthalene sulfonate, and sodium N-methyl-N- (long chain) acid.

Typical wettable powders contain 25 to 90% of active ingredient, 0.5 to 2.0% of wetting agent, 0.25 to 5.0% of dispersant and 9.25 to 74.25% by weight of inert extender. Of the extender, 0.1 to 1.0% is often replaced by an anti-corrosion agent and / or an antifoam agent.

22 E. GENERAL 70224

In general, any conventional post-emergence application method can be used, including conventional dusting or spraying equipment. The amount of active ingredient that effectively produces the desired result, whether it is a herbicidal or growth-regulating effect, depends on the plant species to be controlled and the prevailing conditions. Herbicidal effects are usually achieved with an application rate of 0.11 to 56.0 kg of active ingredient per hectare, preferably 1.1 to 11.2 kg, while a plant growth regulating effect is usually achieved with an application rate of 0.11 to 22, A kg of active ingredient per hectare, preferably 0 , 56 - 5.60 kg. It is apparent to the mother imi that compounds with lower activity require a higher dosage than more active compounds in order to have the same control effect.

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Claims (9)

A compound of the formula r3 I n 0 R2 “? <0) n M I ^ P-CH2NHCH2 COH · R, HCT wherein R1, R2 and R3 are the same or different and represent C1-C8 alkyl, and n is zero or one. Compound according to Claim 1, characterized in that R 1 to R 3 are methyl and n is zero. 2 “70224 Compound according to Claim 1, characterized in that R 1 to R 3 are methyl and n is one. A compound according to claim 1, wherein n is zero, characterized in that R 1 and R 2 are each n-butyl and R 3 is methyl. A compound according to claim 1, wherein n is zero, characterized in that R 1 and R 2 are each ethyl and R 3 is methyl. A compound according to claim 1, wherein n is zero, characterized in that R 1 and R 2 are each methyl and R 3 is isopropyl. A compound according to claim 1, wherein n is zero, characterized in that R 1 and R 2 are each methyl and R 3 is n-butyl. 8. A mixture useful as a herbicide and a plant growth regulator, characterized in that it contains an active I! 70224 in the amount of a compound of formula or one, and at least one excipient. A herbicidal or method for regulating the natural growth or development of plants, characterized in that an effective amount of a compound of the formula? 3 o o R2-S (0) n © Θ Ov I | 2. n 1; P-CH 2 NHCH 2 COH R, Ho / wherein R 1, R 2 and R 3 are the same or different and represent C 1 -C 6 alkyl, and n is zero or one. 70224