HU189602B - Herbicide and plant growth regulating compositions containing n-phosphono-methyl-glycine-phosphonium salts - Google Patents

Abstract

The invention relates to herbalicide compositions for use in agriculture. The aim of the invention is to provide novel compositions for use as herbicides and plant growth regulators. According to the invention, as active ingredient in the novel herbicidal compositions, novel phosphorus salts of N-phosphono-bi-glycine are used with the formula in which R1, R2, R3 and R4 are in each case inactive from the C1-C10-alkyl, phenyl, benzyl, sub-substituted benzyl WHEREAS THE SUBSTITUTES IN QUESTION ARE SELECTED INDEPENDENTLY OF HALOGEN, A LOW ALKOXY GROUP OR A LOWER ALKYL GROUP, PROVIDED THAT AT AT LEAST ONE OF THE RADICALS R1, R2, R3 AND R4, BENZYL, SUBSTITUTED BENZYL OR SUBSTITUTED PHENYL ACT.

Description

FIELD OF THE INVENTION The present invention relates to herbicidal and plant growth controlling compositions containing N-phosphonomethylglycine phosphonium salts.

N-phosphonomethylglycine is a well-known chemical compound and is commercially available as a mono-isopropylamine salt in herbicidal formulations and as a sodium salt as a sugarcane growth regulator. .

In our work, we have discovered that new salts of N-phosphonomethylglycine can be used as active ingredients in post-emergence herbicides and plant growth regulators. the type and frequency of weeds and the amount of agent used, and the determination of a specific combination of such factors is within the routine work of one skilled in the art.

A herbicidal effect is when the weeds or, in general, unwanted plants are partially or completely extinct. Partial eradication is often more expedient for economic reasons. Plant growth regulating effects are more varied and include both defoliation and retardation of vegetative growth.

By defoliation, we increase the growth of productive plant parts and facilitate harvesting.

There are different ways to delay vegetative growth.

In some plants, it causes a reduction or loss of upward growth, a shorter strain and an increase in the number of side branches. As a result, smaller bushy plants are obtained which are more resistant to drought and insect pests. Delaying vegetative growth is also useful when creating racetracks on racetracks, as it reduces vertical growth, promotes root growth, and results in denser, stronger grassland. Delaying the growth of lawn increases the intervals required for mowing lawns, golf courses and similar lawns. Reducing vegetative growth in silage plants, potatoes, sugar cane, sugar beet, grapes, melons and fruit trees increases the carbohydrate content at harvest. It is believed that delaying or suppressing growth at the appropriate stage of development reduces the amount of carbohydrate used for vegetative growth and thus increases the starch and / or sugar content. Delaying vegetative growth results in shorter branches and more dense form of fruit trees and often less vertical growth. These factors contribute to the ease of gardening and facilitate fruit harvesting.

The novel N-phosphonomethylglycine salts useful as active ingredients in compositions for controlling unwanted vegetation and controlling natural plant growth or development contain substantially substituted phosphonium cation and glycylmethylphosphonate anion. The salts may be represented by the general formula (fi). In this formula

R ¹ , R ⁵ , R ³ and R ⁴ are each independently 1-6 carbon atoms, a benzyl group optionally substituted twice with halogen, or a phenyl group optionally substituted with up to two halogen atoms, C 14 alkyl or C 14 alkoxy, provided that At least one of R ¹ , R ¹ , R ³ and R ^{4 is} a benzyl group or a phenyl group substituted with up to 2 carbon atoms and up to 2 carbon atoms with a halogen atom.

Highly active are the salts wherein R ¹ , R ² , R ³ and R ⁴ are independently C 1 -C 6 alkyl or phenyl.

Particularly effective compounds of formula I are those wherein R ¹ , R ² , R ³ , and R ⁴ are each independently C 1-6 alkyl, phenyl, benzyl, substituted phenyl wherein the substituent is chloro, lower alkyl or lower alkoxy.

Even more effective are those compounds of formula (I) wherein R ¹ , R ² , R ³ and R ⁴ are the same and are C 14 alkyl or phenyl.

The lower alkyl and lower alkoxy groups have 14 carbon atoms, linear or branched. Examples include methyl, ethoxy, propyl, propoxy, butyl, isobutyl or butoxy.

The compositions of the invention can be used to control unwanted vegetation after emergence.

The compositions may also be used to control the natural growth of plants.

The amount of spray herbicide denotes the amount of active ingredient in the composition of the invention that will kill the plant or significantly inhibit its growth. By "plant" is meant germinating seeds, hatched seedlings and mature plants, including roots and subterranean parts.

“Natural growth or development refers to the normal life cycle of a plant without any external artificial influence. The compositions of the invention can be used advantageously to increase the sugar content of free-growing sugar cane and sugar sorghum. "Regulatory designation", as used herein, means the use of chemical means to cause temporary or permanent alteration or change in the normal life cycle of plants.

According to the invention, weed control is most effectively achieved by applying the formulations containing the active compounds of the formula I after emergence to the weeds. On the other hand, control of the natural growth or development of plants is achieved by applying these formulations to the plant or any part of it above ground 4 to 10 weeks immediately prior to harvest. An amount suitable for controlling plant growth is used to achieve the latter effect. It is known in the art that the effective amount for this purpose will vary not only with the agent selected for treatment, but also with the regulatory effect desired, the plant species to be treated and their state of development, and both permanent and transient regulatory effects have been addressed. The appropriate amount is determined by the application method and the weather conditions such as temperature and rain. The result is the effect of the chemical regulator on both the physiological processes and the morphology of the plant, or a combination of the two.

Morphological changes are generally well visible on the treated plant, namely changes in the size, shape, color or structure of the plant or plant part and the amount of flower or fruit produced by the plant. On the other hand, physiological changes occur in the treated plant and are usually not visible. These types of changes are most often changes in the production, distribution, accumulation or utilization of substances naturally occurring in the plant, such as hormones. Such changes may be followed by morphological changes that can be detected by analytical methods known in the art. Regulatory effects can be achieved in a variety of ways, depending on the species of plant or the amount of regulator used.

The compounds of formula (I) are readily prepared from N-phosphonomethylglycine by reaction with appropriately substituted phosphonium halide in the presence of propylene oxide. N-phosphonomethylglycine itself can be obtained by phosphonomethylation of glycine, reaction of ethylglycinate with formaldehyde and diethylphosphite, or oxidation of N-phosphinomethylglycine. Such methods are described in U.S. Patent No. 3,799,758.

The compounds of formula (I) may also be prepared by combining one equivalent of N-phosphonomethylglycine and one equivalent of an organic salt in a mixture of methanol and water. Silver oxide is then added in an equivalent amount in small portions over a period of time and the reaction mixture is stirred for several hours. The product is isolated by conventional means such as filtration and subsequent concentration of the homogeneous solution.

The following examples serve to illustrate the invention, including the preparation of the compositions and their active ingredient, and the use of the compositions for controlling unwanted vegetation and regulating plant growth without limiting the invention.

Example 1

Preparation of N-phosphonomethylglycine monotetra (n-butyl) phosphonium salt A weight% aqueous solution of the N- (phosphonomethyl) -glycine monoisopropylamine salt was prepared. Dilute 0.125 mol) with water (75 mL) and add 12 N hydrochloric acid (10.4 mL, 0.125 mol). The reaction mixture was stirred for one hour and the solid product was collected by filtration. The product was washed successively with water, ethanol and acetone and then oven dried. 15.8 g of N-phosphonomethylglycine are thus obtained. (yield: 75% of theory).

3.4 g (0.02 mol) of this material are combined with 6.8 g (0.02 mol) of tert-butyl-phosphonium bromide and 20 ml of propylene oxide in 100 ml of water. The mixture was carefully heated at 50 ° C for thirty minutes, then the water and volatiles were distilled off to give 11.0 g of a clear oil having a refractive index of n ° - 1.5851. Product identity was confirmed by ¹³ CNMR and IR spectroscopy. The product is an N-phosphonomethylglycine mono [tetra (n-butyl) phosphonium] salt.

Example 2

Preparation of N-phosphonomethylglycine mono- (tetramethylphosphonium) salt

1.4 g (0.0083 mol) of the N-phosphonomethylglycine prepared in Example 1 are combined with 1.8 g (0.0083 mol) of tetramethylphosphonium iodide in 100 ml of water. heat and stir for one hour. The reaction mixture was cooled to 15 ^e C and 6 ml of propylene oxide was added and stirring was continued for two hours. The reaction mixture was then extracted with 150 ml of diethyl ether. The aqueous phase is distilled off to give 30 g of product. The product was then dissolved and stripped with tetrahydrofuran and ether to give 2.3 g of a solid, m.p. ¹³ C-NMR showed the product to be an N, N-phosphonomethyl) glycine mono (tetramethylphosphonium) salt.

Example 3

Preparation of N-phosphonomethylglycine mono (tetraphenylphosphonium) salt

The procedure described in Example 2 was carried out using 1.7 g (0.01 mole) of N-phosphonomethylglycine, 4.66 g (0.01 mole) of tetraphenylphosphonium iodide and 3 ml of propylene. oxide. 6.2 g of a liquid product are obtained with a refractive index ηθ = 1.5768, the product being an N-phosphonomethylglycine mono (tetraphenylphosphonium) salt, as confirmed by ¹³ C NMR.

Example 4

For the preparation of the N-phosphonomethylglycine monopributyl-2,4-dichlorobenzylphosphonium salt

In the same manner as in Example E1, 2.11 g (0.0125 mole) of N-phosphonomethylglycine, 4.97 g (0.0125 mole) of tributyl-2,4-dichlorobenzyl are obtained. Phosphonium chloride and 1.1 g of propylene oxide are used. After two days, the reaction does not start. (Phosphonomethyl) glycine is still visible (not dissolved). About 20 mL of water was removed in vacuo to recover the propylene oxide. Sodium hydroxide pellets (0.5 g, 0.0125 mol) were then added to the resulting solution. After dissolving the N-phosphonomethylglycine, the solution was refluxed for 1.5 hours, stripped, and the solution was triturated with methylene chloride (toluene, filtered) to give 1.6 g of a white solid. .

The product has a melting point of> 320 ° C. After stripping the toluene filtrate, the residue (7.3 g) was triturated three times, decanted with diethyl ether and after each treatment. The solvent was then removed to give 6.6 g of product as a clear viscous oil. The two products were combined and the volatiles removed in vacuo. 7.3 g of crude product are thus obtained. This material is redissolved in water to give a homogeneous solution. The total volume of the aqueous solution was 16.5 g. 40% of the solution contains 4.4% sodium chloride.

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Example 5

Preparation of N-phosphonomethylglycine mono (benzyl triphenylphosphonium) salt

Benzyl triphenylphosphonium chloride (3.9 g, 0.01 mol) was dissolved in water and methanol (0.4 g, 0.022 mol), and ethyl N- (1.7 g, 0.01 mol) was added to the solution. phosphonomethyl) glycinate. Silver oxide (2.43 g, 0.0105 mol) was then added in small portions over an hour. After the addition was complete, the mixture was stirred for an additional two hours. The silver nitrate solution indicates that no halogen is present since no precipitate forms when a few drops of supernatant liquid is added. The silver chloride and silver oxide were separated by filtration and the filter cake washed with methanol. The filtrate was stripped at 25 ° C to give 5.5 g of a white crystalline solid, m.p. 78-82 ° C. The product is hygroscopic but soluble in water or chloroform. The identity of the product was confirmed by ³ C-NMR.

Example 6

Preparation of N- (Phosphonomethyl) glycine-noniono (ethyl triphenylphosphonium) salt

Ethyl triphenylphosphonium iodide phosphonium salt (4.2 g, 0.01 mol) was combined with ethyl N-phosphonomethylglycine (1.7 g, 0.01 mol). Then 150 ml of methanol are added and the phosphonium salt is dissolved. Water (0.4 g, 0.22 mol) was then added and the solution was stirred in small portions over one hour at room temperature with silver oxide. The reaction mixture was stirred for 2.5 hours at room temperature. The silver iodide and excess silver oxide were collected by filtration and the filtrate stripped. 4.6 g of product are obtained, m.p. 59-68 ° C. Product identity was confirmed by NMR, IR spectroscopy and ¹ C NMR.

Example 7

Preparation of N-Phosphonomethylglycine mono [methyl-tn (p-tolyl) phosphonium salt

The procedure described in Example 6 was followed and 4.46 g (0.01 mol) of methyl tri (p-tolyl) phosphonium iodide were combined with 1.7 g (0.01 mol) of N-phosphonomethyl) glycine. , then add methanol and water to the mixture.

Silver oxide was then added over a period of 40 minutes, and after the addition was complete, the reaction mixture was allowed to stand at room temperature for 2 hours. The silver oxide and silver iodide are then separated by filtration and the resulting filtrate is stripped at 25 ° C and under 1.33 mbar. In this way, 4.8 g of the title compound are obtained as a potassium melting point, m.p. 75-85 ° C. The product is hygroscopic. The identity of the compound was confirmed by NMR spectra, ¹³ C-NMR spectra and IR analysis.

EXAMPLE 8 Preparation of N-Phosphonomethyl-glycine-minino [methyltri- (4-methoxyphenyl) phosphonium] salt. (01 mol) of methyl tri (4-methoxyphenyl) iodide and 1.7 g (0.01 mol) of N - (- phosphonomethyl) 2 O -glycine. Silver oxide was added portionwise over 30-40 minutes, the whole was stirred for 20 minutes at 20 ° C, and the silver iodide and silver oxide were separated by filtration. The filtrate was stripped in vacuo at 25 ° C and under 1.33 mbar to give 5.3 g of a white powder, m.p.

M.p. 60-68 ° C and hygroscopic. The structure

Nuclear Magnetic Resonance Spectrum, ¹³ C-NMR Spectrum and IR analysis confirmed.

Example 9

Preparation of N- (Phosphonomethyl) glycine mono [methyltri (4-chlorophenyl) phosphinium salt

The procedure described in Example 6 was followed by combining 5.08 g (0.01 mole) of methyl tri (4-chlorophenyl) iodide with 1.7 g (0.01 mole) of N- (phosphonomethyl) Gly). Silver oxide (sulfur oxide) was then added to the mixture over 40 minutes and after the addition was complete, the reaction mixture was stirred at room temperature for 2.5 hours. The silver oxide and silver iodide were separated by filtration and the filtrate was stripped at 25 ° C and a pressure of less than 1.3 mbar. This gave 55 g of the title compound, m.p. 85-95 ° C and hygroscopic. The structure was confirmed by NMR and IR analysis.

Table A Compounds of Formula I

Example Physical constant

number ^R 9 ^R 3 ^R 4 n ³ ® or Op. First ~ nC ₄ H ₉ ⁿ -U ₄ IT ₉ ”Ft-C ₄ H ₉ - rron- Second Third CH. phenyl • ^CH 3 phenyl CH. phenyl -CH- phenyl 80 ° C (dec.) ], 5768 4th n-C ^ Hg nC ₄ H ₉ 2,4-dichlorobenzyl 32O DEG C. 5th phenyl phenyl phenyl benzyl 78-82 ° C 6th -c ₂ h ₅ phenyl phenyl phenyl 59-68 ^c C. 7th 4 CHyfenil 4 CHyfenil 4-CH ₃ -phenyl -ch ₃ 75-85 ° C 8th 4-CH ₃ O-phenyl 4-CH ₃ O-ferdl 4-CH ₃ O-phenyl ch ₃ 60-68 ° C 9th 4-Cl-phenyl 4-Cl-phenyl 4-Cl-phenyl -ch ₃ 88-85 ° C

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Example 10 Herbicidal activity

The following examples illustrate the post-emergence herbicidal activity of formulations containing the active ingredient of formula (1).

Aluminum seedling pots measuring 15.2 x 22.9 x 8.9 cm were filled to a depth of 7.6 cm with clayey sand soil containing 50 ppm of the cis - [(trichloromethylthio) 4-cyclohexene-1,2-dicarboxylamide commercial fungicide (Captan). and the so-called 17-17-17 fertilizer (NJNOj-KO% by weight). Seven rows were selected on the surface of each tile and seeded with different grasses and broadleaf weeds. The weed species were as follows:

Broad-leaved weeds:

A. Annual Garden River Price

B. Sea buckthorn

C. Maslag

C. l Henning

D. Selyempeije

E. Wild Mustard

F. Csucsor F.l Sululs

F. 2 Rhizome

G. Pig Parsley Grasses:

H. Yellow mud

I. Rye

J. Brush Lawn

Ipomea purpurea

Xanthium sp.

Datura stramonium Sesbania exhalta Abutilon theophrasti Brassica sp.

Solanium sp. Convulvulus arvensis Cassia obtusiflora Amaranthus sp.

2C

Cyperus esculentus Bromus tectorum Setaria sp.

grasses:

K. Perje Lolium multlflorum

L. Cocksfoot Echinochloa crusgalli

M. Narancsköles Sorghum bicolor

M. l Fragile millet Sorghum bicolor

N. Vadzab Avena fatua

Broad-leaved varieties were sown first and four days later the grasses were sown. Seeds of each variety were sown enough to produce 5 to 50 seedlings per row, depending on the size of the plant.

Ten days after sowing, all weed seedlings were sprayed with aqueous solutions of the test compound. The solutions were prepared in dilutions such that after spraying 750 liters / ha, the spray rate was between 0.28 and 4.48 kg / ha, resulting in 0.03 Vfc, 0.15% w / v,

O. Spray broths containing 3%, 0.45% and 0.6% of active ingredient were used. Untreated plants were used for comparison to determine the extent of weed control.

After nineteen days, the plants in the treated pots were compared with the untreated plants and the percentage eradication effect, which may be between 0% and 100%, was visually determined for each row. 0% indicates the same degree of development as the standard line value, while 100% indicates the death of all weeds in the row. All types of plant damage were considered. The results are shown in Tables I and II. are each independent series of experiments.

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189,602

Example 11 da

Herbicidal effect

This example illustrates the pre-emergence and post-emergence effects of the same three active ingredients ρ on different grasses and broadleaf weeds at 4.48 kg / ha. Some weeds such as those of Example 10 were used in Table III, Table III, using the same designations as in Examples I and II. 10), but the method was similar, but in the pre-emergence test, the bowls were sprayed with the test compound formulation on the day after sowing and the degree of damage was evaluated thirteen days after, and in the post-emergence test, the plates were sprayed ten days after sowing. and the extent of the damage was determined thirteen days later. The results are shown in Table III. table.

For post-emergence treatment, comparative studies were also conducted using the compound disclosed in U.S. Patent 4,399,758, N- (phosphonomethyl) glycine manganese salt hemihydrate (Compound B). The results are also a

III. table.

From the results it can be seen that the herbicides are effective in the post-emergence application of the compositions according to the invention and their activity is superior to the known compositions.

III. Spreadsheet

Herbicidal test results before and after hatching

Test substance Mono-) tetra- (n-outil) - Percentage removal Application THE D E G H J L N before hatching "FIVE 'She ΊΤ 0. 0 0 phosphonium] -salt after hatching 70 80 95 95 75 100 100 75 Mono (tetramethyl-phosphate before hatching 0 0 0 0 0 0 0 0 triphenyl phosphonium) salt after hatching 98 85 100 90 65 100 95 90 Compound A after hatching 40 65 55 ⁺ 75 45 75 45 30 Compound B: after hatching 20 45 20 ⁺ 35 35 75 35 0 Note: +: We tested horse roma instead of pork.

Example 12

Plant growth regulating effect

This is an example of N- (phosphonomethyl) glycine mono-

demonstrates the effect on your mood.

The experimental method was as follows:

A series of 12.7 cm diameter and 12.7 cm deep volcanic fiber tiles filled with sandy clay pots filled with enough so-called "clay". 17-17-17 fertilizer was added to reach 150 ppm N and I / O. A series of sorghum seeds were sown and the pots were placed in a greenhouse, the temperature being maintained at 27 ° C during the day and 21 ° C at night. The seedlings were gutted after emergence, leaving one plant in a pot. Root and root shoots were removed as they appeared before treatment of the plants. The pots were fertilized at certain intervals with a so-called fertilizer. 17-17-17 with fertilizer.

Nine weeks and four days after planting, the stem length to the maxillary apical membrane was measured and the plants were sprayed with an aqueous solution of the test compound containing 0.5% by weight of a polyoxyethylene sorbitan monolaurate surfactant. The sprayer used was carbon dioxide and was a bicycle type. The test solution was sprayed at a rate of 234 liters / hectare and the active compound concentration was determined to be between 0.56 and 4.48 kg / ha and therefore 0.1%, 0.2%, 0.45t. % and 1.8% by weight spray liquid was used

After ten days, the plants were picked, the stalks were cut off at the ground level, and the leaves and pods were removed. The stem length to the highest visible dorsal membrane was again measured. These g measurements and the spray measurements were replaced by the following formula to determine "percent stem picking:

Percentage) length at the time of picking stem lengths - BUCKing JJ length spraying

L time

-1,0x100

We then measured the stems to ground level) up to the top node and called this "stem length". The dorsal and peduncle (the part of the stem from the uppermost knot to the bottom of the coat of arms) was then cut off, and the so-called yfriss weight of each of the remaining stems was recorded. Each stem was then cut into small pieces 3.8 cm long ^and extruded on a Carver press at 10.340 N / cm ^s . The "amount" of juice from each stalk was determined and also the "total solids" by weight was determined using a suitable refractometer. The extruded stems were air-dried and weighed ("dry weight").

The results of the TV. Table 3 shows the mean of three untreated control plants for comparison. The table shows the decrease in stem elongation, the fresh weight and dry weight, and the percentage increase in total solids solids in the pressed juice.

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ARC. spreadsheet

Accomplishments in sugar content in sweet sorghum

Test compound Alk. heaven.  (Kg / ha) Szárhosz- szabbodási percentage Shit juice Length (Mm) F.W. (G) D. W. (G) T.D.S. (%) Heaven. (Ml) Checker -52jT- 26Γ - 3,3b -44- -97T ~ Mono (tetra (n-butyl) phosphonium] - 1.12 4.8 110 10.0 1.22 7.0 1.8 salt. 2.24 3.4 105 109 1.23 7.6 3.0 4.48 5.3 160 16.3 1.80 3.5 7.4 Mono- [tetramethyl phosphonium] - 0.56 5.4 185 24.4 3.52 12.4 6.6 -SALT 1.12 2.3 255 26.2 2.75 7.0 7.6 2.24 4.5 245 23.9 2.19 7.4 8.6

"F.W., ·. fresh weight 'D.W'. ^ dry weight "T.D.S,": total solids soluble * Average of three replicates

application Profiles

For outdoor use, the active compounds of the present invention are formulated into suitable formulations containing additional diluents and carriers. Such diluents or carriers include water, organic solvents, powders, granules, surfactants, water-in-oil and oil-in-water emulsions, wetting agents, dispersing agents, and emulsifying agents. The compositions may generally be in the form of powders, solutions, emulsifiable concentrates or wettable powders.

A. Porok

Powders are solid powder formulations containing the active ingredient together with a dense, free-flowing solid carrier. They are intended to be used in dry form and must settle rapidly to avoid release into the air where their presence is undesirable.

The carriers may be of mineral or vegetable origin, and are preferably organic or inorganic powders of high bulk, low surface area, and less fluid absorption. Preferred excipients are talc, pyrophyllite, dense kaolin chalk, tobacco powder and ground calcium phosphate.

The appearance of a powder composition can often be improved by adding a liquid or solid wetting agent, which may be ionic, anionic or non-ionic. Preferred wetting agents include alkyl benzyl and alkyl naphthalene sulfonates, sulfated fatty alcohols, amines or acid amides, long chain esters of sodium isothionate, esters of sodium sulfosuccinate, sulfates or sulfonated fatty acid esters of sulfonated fatty acids, in the powder formulation. Typical dispersants include methylcellulose, polyvinyl alcohol, lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalenesulfonate, polymethylene bisnaphthalenesulfonate and sodium N-methyl-N- (long chain acid taurates).

In addition, inert absorbent grinding aids may be added to the powders. Suitable grinding aids include attapulgite chalk, diatomaceous earth silica, synthetic fine silica and synthetic calcium and magnesium silicates.

In typical powder formulations, carriers generally contain from 30 to 90% by weight of the total composition. The grinding aid is typically 5 to 50% by weight and the wetting agent is about 1.0% by weight. The amount of dispersant present in 30 is not more than 0.5% by weight. Additionally, small amounts of anti-caking and antistatic agents may be present in the powder formulations. The entire composition will typically have a particle size of 30-50 microns.

β. solutions

Aqueous solutions of the active compounds are prepared by:

Provide 9-1875 liters of active ingredient per hectare. The solutions contain small amounts, such as 0.05-0.5% by weight of non-phytotoxic surfactant, to increase the wettability of the solution and to facilitate distribution to the plant surface. Anionic, cationic, nonionic, amphoteric and covalent surfactants can be used.

Suitable anionic surfactants include the alkali metal, ammonium and amine salts of fatty alcohol sulfates having 8 to 18 carbon atoms in the fatty chain and sodium salts of alkyl benzene sulfonates having 9 to 15 carbon atoms in the alkyl chain. Suitable cationic surfactants include quaternary dimethyldialkylammonium halides containing C8-C18 alkyl groups. Suitable nonionic surfactants are the poly (oxyethylene) adducts of C 10 -C 18 fatty alcohols and poly (ethylene oxide) condensates of C 6 -C 12 alkyl chain phenols in which 5 to 25 moles of ethylene oxide are condensed. phenols, cc and condensates of sorbitan esters with polyoxyethylene oxide in which 1040 moles of ethylene oxide condenses with every mole of sorbitan esters. Suitable amphoteric surfactants include secondary and tertiary aliphatic amine derivatives in which an aliphatic substituent has from 8 to 18 carbon atoms and a magnesium substituent from an anionic soluble group, such that

189 (, O2) sulfate or sulfonate. For example, sodium 3- (dodecylaminopropionate) and sodium 3- (dodecylamino) propanesulfonate. Suitable bonded surfactants include aliphatic quaternary ammonium derivatives in which an aliphatic substituent is 8-18. and other anionic water-soluble groups, such as 3- {N, N-dimethyl-N-hexadecylammonio) -propane sulfonate and 3- (N, N-dimethyl-N-hexadecylammonio) 2- hydroxypropane-1-sulfonate.

C. Emulsifiable concentrates

Emulsifiable concentrates are solutions in which the active compounds and the emulsifier are dissolved in a water immiscible solvent. Prior to use, the concentrate is diluted with water to form a suspended emulsion of the solvent droplets.

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

Typical emulsifiers are anionic and nonionic surfactants, or mixtures of the two. Examples are mercaptan polyethoxy alcohols, alkylaryl polyethoxy alcohols, sorbitan fatty acid esters, polyoxyethylene ethers with sorbitan fatty acid esters, polyoxyethylene glycol with fatty or resin acids. esters, fatty alkyloylamide condensates, calcium and amine salts of fatty alcohol sulfates, oil-soluble petroleum sulfonates, or preferably mixtures of these emulsifiers, such emulsifiers usually account for 1 to 10% by weight of the total composition.

The emulsifiable concentrates preferably contain from 15 to 50% by weight of the active ingredient, 40 to 82% by weight of the solvent and 1 to 10% by weight of the emulsifier. These formulations may also contain other additives, such as spreading agents and adhesives.

D. Wettable Powders

Wettable powders are water-dispersible compositions containing, in addition to the active ingredient, an inert solid filler and one or more surfactants to facilitate rapid wetting and to prevent flocculation when suspended in water.

Suitable solid fillers are both natural minerals and products derived from these materials synthetically. Examples are kaolinites, attapulgite chalk, montmorillonite chalk, synthetic silica, synthetic niagnium silicate and calcium sulfate dihydrate.

Suitable surfactants for these formulations are nonionic and anionic, depending on wetting agents and dispersants. The formulations usually contain both. Preferred wetting agents include alkyl benzene and alkyl naphthalene sulfonates, sulfated fatty alcohols, amines or acid amides, long chain acid esters of sodium isothionate, sodium sulfosuccinate esters, sulfonated or vegetable oils. Preferred dispersants are methylcellulose, polyvinylalkiolol, lignin sulfonates, polymer alkylnaphthalenesulfonates, sodium naphthalenesulfonates, polymethylene bisulululphinylphonates and sodium N-methyl-N-long chain.

Wettable powders contain from 25 to 90% by weight of active ingredient, 0.5 to 2.0% by weight of wetting agent, 0.25 to 5.0% by weight of dispersant and 9.2574.25% by weight of inert filler. Preferably, the wettable powders contain corrosion inhibitors and / or antifoams instead of 0.1 to 1.0% by weight of filler.

E. General remarks

In general, any conventional application can be used, except for conventional dusting and spraying devices. The amount of active ingredient used to achieve the desired result, both herbicidal and plant growth controlling, depends on the nature of the plant species to be controlled or controlled and the prevailing conditions, Herbicidal effects are generally 0.12 -56 kg / ha, preferably 1.12-11. 2 kg / ha of tracer, while the plant growth control effect requires 0.112-22.4 kg / ha, preferably 0.56-5.6 kg / ha of active ingredient. It will be apparent to those skilled in the art that, in the case of a less active agent, a greater amount is required to achieve the same degree of effect as when a more active agent is used.

The composition of the compositions of the present invention is illustrated by the following examples.

Emulsifiable concentrate

(a) Commercially available emulsifier kerosene (solvent) containing a mixture of N- (Phosphono-methyl) -Guine-mono (tetrantethylphosphonium salt calcium dodecylbenzenesulfonate and ethoxylated alkyl phenols)

b) Commercially available emulsifier kerosene (solvent), by weight, containing 10% by weight, 90% by weight of an emulsifier containing a mixture of N-phosphonomethylglycine mono- (tetraphenylphosphonium) salt and calcium dodecylbenzenesulfonate and ethoxylated alkylphenols. % by weight 3% by weight

Granulate

a) N- (Phosphonomethyl) glycine mono [tetra- (n-butyl) phosphonium] salt 0.5 wt% attapulgite 99.5 wt%

b) N- (Phosphonomethyl) glycine mono (tetramethylphosphonium) salt 40 wt% attapulgite 60 wt%

Claims (13)

PATENT CLAIMS CLAIMS 1. A herbicidal and plant growth regulator composition comprising as an active ingredient 0.01-95% by weight of an N-phosphonomethylglycine phosphonium salt of the formula (I): R, R, R and R are independently C 1-6 alkyl, benzyl optionally substituted with halogen, or phenyl optionally substituted with up to two halogen atoms, C 1-4 alkyl or C 14 alkoxy monosubstituted. 189 602 with the proviso that at least one of R ¹ , R ² , R ³ and R ⁴ is benzyl or phenyl substituted at most two times by halogen at C 14 alkyl, one or more excipients such as solvents, preferably kerosene, a carrier, preferably attapulgite, and optionally a surfactant, preferably a mixture of calcium dodecylbenzenesulfonate and ethoxylated alkyl phenols. (Priority: 05/05/1982) Composition according to Claim 1, characterized in that it contains as an active ingredient a compound of the formula (I) in which R, R, R ³ and R ⁴ are independently C 1-6 alkyl or phenyl. (Priority: Aug 24, 1981) 3. A composition according to claim 1, wherein the active ingredient is an aliphatic-burned compound of formula (I) wherein R ¹ , R ² and R are independently C 1-6 alkyl or phenyl and R ⁴ benzyl, or phenyl optionally substituted with up to two substituents on the halogen atom or on a C14 alkyl or C14 alkyl moiety. (Priority: 05.05.1982). 4. A composition according to claim 1 wherein the active ingredient is a compound of formula I wherein R ¹ , R ² and R ³ are each n-butyl and R ⁴ is 2,4-dichloro. benzyl. (Priority: 05.05.1982). 5. A composition according to claim 1, wherein the active ingredient is a compound of Formula U wherein R ¹ , R ² and R ³ are each phenyl and R ^{4 is} benzyl (Preferred; 05.05.1982). 6. A composition according to claim 2, wherein the active ingredient is a compound of formula I wherein R ^{1 is} ethyl and R, R ³ and R ⁴ are each phenyl. (Priority: Aug 24, 1981) 7. A composition according to claim 1 wherein the active ingredient is a compound of formula I wherein R, R ² and R ³ are each p-tolyl and R ^{4 is} methyl. (Priority: 05.05.1982). 8. The composition of claim 1, wherein je 1 I e uniform ve to an active ingredient comprising (I) a compound of the formula wherein R, R ² and R ^S are both 4-methoxyphenyl group, and R4 is methyl. (Priority: 05.05.1982). 9. A composition according to claim 1, wherein the active ingredient is a compound of general formula (I) wherein R, R ² and R ³ are each 4-chlorophenyl and R is methyl. 05.05.1982). 10. The composition of claim 2, wherein the active ingredient is a compound of formula (I) wherein R ¹ , R, R ³ and R ⁴ are the same and are C 14 alkyl or phenyl. (Priority: Aug 24, 1981) 11. The composition of claim 2, wherein the active ingredient is of formula (I). contains a compound wherein R ¹ , R ² , R ³ and R ⁴ are each methyl (Priority: 24.08.1981) 12. A composition according to claim 2 wherein the active ingredient is a compound of formula (I) wherein R ¹ , R ¹ , R ³ and R ⁴ are each n-butyl. (Priority: Aug 24, 1981) 13. The composition of claim 2 wherein the active ingredient is a compound of formula I wherein each of R ¹ , R ¹ , R ³ and R ⁴ is phenyl. (Priority: Aug 24, 1981)