HU195723B - Herbicides and growth regulators comprising phosphoric acid-containing acetic acid derivatives as active ingredient and process for producing the compounds - Google Patents

Abstract

The present invention relates to a herbicide and a growth regulating composition comprising 0.03 to 60% by weight of the compound of formula (I), wherein R1 and R1 are each independently the same or different C1-2 alkyl; R 3 is -OH, C 1-10 alkoxy, phenoxy, benzyl, halobenzyloxy, C 2-4 alkyloxy, C 2-4 alkenyloxy, C 1-4 alkyl benzyloxy, C 1-4 alkoxy benzyloxy or hydrazinoc swept; R1 is hydrogen or CO-NRsRc, wherein R5 is hydrogen and R6 may be halogen-substituted C3-C6 alkylsulfonyl - and their base salts with the usual solid carrier, preferably quartz, talc or liquid carriers, preferably with an organic solvent, water or mineral oil, optionally with surfactants, preferably anionic or nonionic surfactant. Further, the invention relates to processes for the preparation of the compounds of formula (I). CH - COR I 0¾ / 1 / I'15723 -1-

Description

That is 54.089027. Japanese Patent Application No. 5,102,195 discloses a phosphonoglycine having the formula (HO) 2P (O) CH (NH 2) -COOH as a herbicidal compound. However, this can only be used against broadleaf weeds if the crop is damaged. It is also known from U.S. Patent No. 2,043,989. Insurrection in the FRG! and R (R1) P (O) CH2C (O) R2 having the formula R and R1 are alkyl and R2 is hydroxy, SH and amino as corrosion inhibitors. Many other phosphorus-containing acetic acid derivatives have been found to exhibit excellent total herbicidal and growth-regulating activity.

The present invention relates to growth regulating and herbicidal compositions containing the compounds of the formula I and their base salts and processes for their preparation.

In the general formula (I)

R 1 and R 2 each independently represent the same or different C 1 -C 2 alkyl, phenyl, benzyl or hydroxy groups;

R 1 is -OH, C 1 -C 10 alkoxy, amino, phenoxy, benzyloxy, halobenzyloxy, C 1 -C 4 alkynyloxy, C 1 -C 4 alkenyloxy, C 1 -C 4 alkylbenzyloxy, C4 -C4 alkoxybenzyloxy or hydrazino;

R 1 is hydrogen or -CO-NR 5 R 6 where R 5 is hydrogen and R 6 is C 1-4 alkyl optionally substituted with C 1-4 alkoxy or C 1-4 alkoxycarbonyl and C 1-6 alkyl substituted with halogen. -Sulfonyl or C3 -C6 alkenylsulfonyl, or phenyl substituted twice with halogen.

When R3 is hydroxy, the compounds of formula (I) may be formulated into salts with inorganic or organic bases. Suitable base cations are, for example, Na ', Κ *, NH 4 *, Ca ² *, Zn ² *, Cu ² *, Fe ² *, Ni ² *, (C 1 -C 4) -alkyl-NH 3 *, di - (C 1-4) alkyl-NH 2 *, tri- (C 1-4) alkyl-NH * or (HOCH 2 CH 2) 3 NH *.

For example, R1-R2 has the following meanings:

Ri. R 2: CH 2, C 2 H 5; R3 : OH, ONH4, ONa, OK, OCH 3, OC2H5, OCH2CH2CL, OCiHsln), OCeHs, NHNH 2, NH2; R4 : CONHCHa, CONHSO2CH3, C0NHSO2CH2C =

= CHCH 3, CON (CH 2 CH = CH 2) 2, CONHCeHs.

The invention also relates to the preparation of compounds of formula (I). The compounds of formula (I) are prepared by:

a) reacting a compound of formula II wherein R 1 and R 2 are as defined above, with a compound of formula III wherein R 3 is as defined above, to form compounds of the formula wherein R 4 is H; and

b) acylating the compounds of formula (IV) wherein R 1 and R 3 are as defined above, optionally with the base, to form compounds having a non-II atom at R 4.

(a) The starting materials of formula (II) are also known (see German Patent Publication No. 1,793,203 and Houben-Weyl, Vol. 1, p. 193) or may be prepared analogously. Compounds of formula (III) are partially repeatable (see Houben-Weyl, Vol. VIII, 217 and 280; Bér 37, 3190 (1904); Ann. 690, 138 (1965)) or may be prepared by appropriate methods. Hydrogenolytic cleavage of the Rio group is carried out using hydrogen in the presence of a palladium / carbon catalyst (e.g. Synthesis 1980, 1028-32). The solvents are the same as the solvents mentioned in a) for the ethyl acetate and the reaction temperature is 0-100 ° C, preferably 10-30 ° C. In some cases, the reaction may be accelerated by the addition of a base; such bases include alkali hydroxide or alcohol, e.g. sodium hydroxide, potassium hydroxide, sodium methylate or potassium tert. butylate or tertiary hydrogen bases, e.g. triethylamine or methyl diisopropylamine.

In process (b), the compounds of formula (IV) can be converted to the final products of formula (I) and the isocyanates by conventional means using isocyanates of formula R4-NCO or chloroformylamines R4R5N-COCl. is used, then R5 = hydrogen. These reactions are known to those skilled in the art.

It is apparent from the general formula (IV) that when a phosphorus compound of the general formula (II) is added to the compound of the general formula (III), an asymmetric center is formed. Thus, the compounds of formula (I) may exist in the form of optical isomers and their preparation is within the scope of the present invention.

The compounds of the present invention exhibit excellent and very broad herbicidal activity against a broad spectrum of perennial and annual weeds at roadside edges, in industrial installations or in railway installations. The present invention therefore relates to herbicidal compositions containing the compounds of the formula I and used for inhibiting undesirable plant growth.

The active ingredients can also be used in agriculture and for weed control. They may be applied to one or more years of crop production provided that the mode of application and / or the age of the crop are ensured, so that the crop or

-2195723 sensitive green parts should not be damaged. Such applications are e.g. plantations, tree plantings and vineyards, etc.

Since the application of the new compounds to crop plants prior to emergence of the crop does little or no harm, weed control can be performed before sowing or before sowing or after harvest.

The compounds of the present invention may also be used in the crop to prevent disturbing growth of the crop, e.g. for cotton and potatoes. Depending on the dose used, the novel compounds may achieve typical plant growth regulating effects, e.g. we can influence the growth of the plants as well as the content of the desired plant materials, e.g. the compounds can be used as growth regulators in crop plants such as cereals, maize, sugar cane, tobacco, rice and sorghum. It is also possible to regulate certain plant stocks, e.g. artificial grasses or ornamental plants on roads and roadsides.

The compounds of the present invention can inhibit the vegetative growth of many monocotyledonous and dicotyledonous plants and, consequently, increase the carbohydrate content of the plants and their fruits. As a result, the content of the desired plant material, e.g. the excess or carbohydrate (starch or sugar) content can be positively influenced.

For example, in sugar cane and sugar beet the sucrose content increases, in fruit and grapes the fruit sugar content increases, in other plants e.g. starch content in potatoes, corn and sorghum (sorghum) and green fodder (clover, alfalfa). The benefits thus obtained are obvious and need not be further explained.

Application takes place one to five months before harvest. When this time passes, the maturation induced by the active ingredients and thus the carbohydrate content reaches a maximum. It should generally be borne in mind that growth rates and vegetation times may vary from one crop to another. For sugar cane, for example. depending on the location and climate, it can take 1-3 years before the plant is ready for harvest. The time of use may also change appropriately. it can be 1-13 weeks before harvest.

Formulations of the invention may be in the form of spray powders, emulsifiable concentrates and spray solutions, dusts, dressings, dispersions, granules or microgranules in conventional formulations.

Spray powders are uniformly dispersible in water formulations which, in addition to the active ingredient and, if appropriate, any diluent or inert material, may also contain a wetting agent, e. polyoxyethylated fatty alcohol, alkyl or alkylphenyl sulfonates and a dispersant such as lignin sulfonic acid sodium,

They may contain 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or oleoylmethylurethic acid sodium. The preparation is carried out in a known manner, e.g. grinding and mixing the components.

The emulsifiable concentrates are e.g. by preparing the active ingredient in an inert organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, kilo or higher in hot aromatic or hydrocarbon with the addition of one or more emulsifiers. In the case of liquid active ingredients, the solvent may be wholly or partially absent. As an emulsifier, e.g. calcium salt of alkylarylsulfonic acid, e.g. calcium dodecylbenzene sulfonate or a nonionic emulsifier, e.g. fatty acid polyglycol ester, alkylaryl polyglycol cholesterol, fatty alcohol polyglycol cholesterol, propylene oxide ethylene oxide condensation products, fatty alcohol propylene oxide ethylene oxide condensation products, alkyl polyglycol cholesterol, polybenzene fatty acid ester, polybutyl ester or poloxide.

The excipients are obtained by contacting the active ingredient with finely divided solids, e.g. talc, natural materials eg. ground with kaolin, bentonite, pyrophyllite or diatomaceous earth.

The granules can be prepared either by applying the active ingredient to the adsorbent granulated inert material or by concentrating the active ingredient in a binder, e.g. with polyvinyl alcohol, sodium polyacrylic acid or mineral oil, e.g. sand, kaolinite or granular inert material. Suitable active ingredients may, if desired, be granulated with fertilizers in a manner known per se for the preparation of fertilizer granules.

In spray powders, the active ingredient concentration is e.g. It may be from 10 to 60% by weight, and the portion up to 100% by weight will consist of conventional formulation aids. In the case of emulsifiable concentrates, the concentration of active ingredient may be from 10 to 60% by weight. The powder formulations generally contain from 5 to 20% by weight of the active ingredient and 2 to 20% by weight of the sprayable solution. In the case of granules, the active ingredient content depends in part on the active ingredient in liquid or solid form and the type of granulation excipient, binder and the like. used.

The aforementioned active ingredient formulations may optionally contain conventional adjuvants, wetting agents, dispersing agents, emulsifying agents, penetrating agents, solvents, fillers or carriers.

Commercially available concentrates are optionally added with diluents, e.g. in the case of spray powders, emulsifiable concentrates, dispersions and, in part, microgranules, the dilution is carried out with water. Dust and granular formulations and sprayable solutions are no longer diluted with other inert materials prior to use. With other active ingredients, e.g. insecticides, acaricides, herbicides, fertilizers and growth regulators or fungicides can also be mixed.

Depending on the purpose of use and the time of application, the concentration of use may vary within wide limits. Concentration for use as herbicide. 0.3 and 10, preferably 0.5-3 kg / ha. When used as a growth regulator, the application rate will of course be lower and will be between 0.1 and 2 kg / ha and the desired concentration may vary widely depending on the crop species.

Further details of the invention are illustrated by the following examples.

A) Production Examples

Example 1

2- (dimethylphosphinoyl) -2-hydroxyacetic acid (2)

15.6 g (0.2 mol) of dimethylphosphinoxide in 80 ml of ethyl acetate. A solution of 14.8 g (0.2 mol) of glyoxylic acid hydrate in 80 ml of ethyl acetate is added dropwise. Meanwhile, the temperature rises slightly. The mixture is stirred for 24 hours at 25 ° C, the product is filtered off with suction, washed with a little ethyl acetate and dried to give 20.2 g (66.5%) of the desired product, m.p. 206-208 ° C.

Example 2

2- (Dimethylphosphinoyl) -2-hydroxyacetic acid methyl ester (3)

To a solution of 15.6 g (0.2 mol) of dimethylphosphinoxide in 50 ml of dioxane is added dropwise a solution of 17.6 g (0.2 mol) of methyl glyoxylic acid in 30 ml of dioxane. After the addition of a late tip of sodium methylate, the mixture was stirred for 24 hours at 25 ° C and the high vacuum removed to remove dioxane, taken up in ethyl acetate and after trituration to give 16.4 g (49.4%) of a colorless product. ° C.

Example 3

Ammonium salt of 2- (dimethylphosphinoyl) -2-hydroxyacetic acid

To a solution of 2-dimethylphosphinoyl-2-hydroxyacetic acid (15.2 g, 0.1 mol) in water (10 ml) was added dropwise a solution of 25% aqueous ammonia (10 g). Meanwhile, the temperature rises to 38 ° C. The mixture was stirred for 1 hour at 25 ° C and concentrated on a rotary evaporator. The residue was first azeotroped with toluene and then boiled with acetonitrile. 14.3 g (3-1.6%) of salt are obtained, m.p. 183-186 ° C.

Example 4

a) 2- (Dimethylphosphinoyl) -2-hydroxyacetic acid propylammonium oxide (5)

To a solution of 15.2 g (0.1 mol) of 2-dimethylphosphinoyl-2-hydroxyacetic acid in 30 ml of water is added dropwise 8.9 g (0.15 mol) of propylamine. Meanwhile, the temperature rises from 23 ° C to 38 ° C. The mixture was stirred for 1 hour at 25 ° C, concentrated on a rotary evaporator and the residue was distilled several times with toluene to remove water. The toluene is removed under high vacuum to give a syrup residue having a refractive index ηο ²² = 1.4869, after which it remains waxy after standing.

b) In an analogous manner, the isopropylammonium salt is obtained which is also formed as a waxy substance.

c-ap) By analogy, the following is obtained: cations salt Példasz. cation Mp (° C) 4c. n-butyl methyl phosphonium oil 4d. hydroxyethyl trimethylammonium oil 4e. trimethyl-sulfonic foxónium 40 4f, benzyl ammonium ammonium 135 4g. cyclohexyl- ammonium 118 4h. pyridin-2-ammonium 108 4i. zinc 115 (decomposes) 4k. potassium 150 41st Ladder-n-Bu methyl-animóníum oil 4m. trimethyl-sulfonic fóíiium 60 4N. Irietanol-am- ammonium oil 4o. lithium 120

Példasz. cation Mp (° C) 4p. tetramethyl- ammonium - 4q. cesium oil Irish. tri-n-propyl Hexadecyl phosphonium oil 4s. triethyl am- ammonium oil 4t. trimethyl ammonium oil 4u. n-butyl-ammonium ammonium oil 4v. allyl ammonium ammonium oil 4w. diethyl am- ammonium 93 4x. calcium 130 4y. pyrimidin-2- -amraónium 107 4Z. copper 188 4aa. aluminum 178 4ab. dicyclohexyl ammonium 128 4 Ac: dodecyl ammonium 69 4AD. barium 133 4AE. hexadodecil- ammonium 80 4AF. di-n-octyl ammonium 87 4AG. n-decyl-am- ammonium 64 4Ah. n-octyl-am- ammonium 68 4 Al. oleyl ammonium ammonium wax 4ak. triphenyl n- butyl phosphonium oil 4AL. tetra-n-Bu methyl phosphonium oil 4am. tri-n-oktiol- ethyl phosphonium oil 4an. cyclopropyl ammonium oil 4ao. sodium oil 4a? magnesium oil

Example 5

Methyl 2- (dimethylphosphinoyl) -2-methoxymethylcarbamoyloxyacetic acid methyl ester (6)

To a solution of 12.5 g (0.075 mol) of methyl 2- (dimethylphosphinoyl) -2-hydroxyacetic acid in 50 ml of absolute dioxane was added 0.2 g of triethylamine first, followed by dropwise addition of 6.6 g (0.075) of mole) of methoxymethyl isocyanate in 20 ml of absolute dioxane. After stirring at 25 ° C for 24 hours, the solvent is filtered off and the residue is recrystallized from a mixture of diisopropyl ether and ethyl acetate. 19.6 g (98%) of the desired product are obtained, m.p. 101 ° C.

Example G

2- (dimethylphosphinoyl) -2-hydroxyacetic acid hydrazide (7) for a solution of g (0.0126 moles) of methyl 2-dimethylphosphinoyl-2-hydroxyacetic acid in 80 ml of ethanol 8, 7 g (0.138 mol) of 80% hydrazine hydrate are added dropwise so that the temperature does not exceed 25 ° C. After stirring for 14 hours at 25 ° C, the mixture was concentrated on a rotary evaporator and the residue was freed from the solvent under high vacuum. Trituration with diisopropyl ether gave 18.8 g (89.9%) of a colorless powder, m.p. 152-155 ° C.

Example 7

2- (dimethylphosphinoyl) -2-hydroxyacetic acid anhydride

16.6 g (0.1 mol) of methyl 2-dimethylphosphinoyl-2-hydroxy-acetic acid are dissolved in 70 ml of methanol, for which ammonia gas is introduced for 10 minutes. After standing for 6 days in a bomb tube, it was filtered at 25 ° C, evaporated and the oily residue was triturated with ethyl acetate. 12.4 g (82.2%) of the amide are obtained, m.p. 155 ° C.

Example 8

2-Hydroxymethylphosphinoacetic acid (9) is added dropwise to a solution of g (0.5 mol) of methane phosphonic acid monoethyl ester in 200 ml of ethyl acetate in 44 ml (0.5 mol) of methyl glyoxylic acid in 100 ml of ethyl -acetate solution. After stirring for 24 hours at 25 ° C, evaporate and remove residual solvent under high vacuum. 87 g of a syrup remain and is heated under reflux for 300 hours with 300 ml of concentrated hydrochloric acid. After evaporation again, the residue is subjected to multiple azeotropic distillations with toluene and the solvent residue is again removed under high vacuum. The remaining residue was crystallized after standing for several days. Trituration with ethyl acetate gave 26.8 g (34.8%) of a colorless powder, m.p. 153157 ° C.

In an analogous manner, the following compounds of formula (I) are obtained:

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Table 1 Compound of formula (I)

Example number Ri R2 r ₄ R3 Mp 9th CH3 CH3 CONHCH3 OCH 3 133 10th CH3 CH3 -CONHCH2COOC2H5 OCH 3 111 11th CH3 CH3 A group of formula (11) cl OCH 3 291-193 12th CH3 CH3 -CONHSO2-CH-CH-CH3 CH3 OCH 3 126-128 13th CH3 Cha -CONHSO2-CH = CH-CH3 OCH 3 185 14th - CgHs -CeH5 H OH 161-162 15th -CeHs -CeHs H OCH 3 159 16th -CeHs -CeHs H -OC iH9 (n) 93 17th Cha -C ₃ H 7 (i) H OH 149 18th -CH2C6H5 -CH2C6H5 H OH 159 19th C2H5 C2H5 H OH 168-171 (Dec) 20th -C4H9 (n) -C ₄ H 9 (n) H OH 180 21st CH3 C2H5 H OH 160-164 22nd CH3 -CIÍ3 H O'l / 2Mg ⁺ * 210 23rd CH3 CH3 H -OCeHisfn) 64 24th CH3 CH3 H -OC7Hi5 <n) 49 25th CH3 CH3 H -OCioH2i (n) 55 26th CH3 CH3 H -OCH2-C6H5 105 27th CH3 CH3 H -OCH2C6 «IBR (p) 99-101 28th -ch ₃ CH3 H -OCHzC -CH 114 29th CH3 Cha H -OCH ₂ C = CH 2 85-91 30th CH3 Cha H -OCeHs 90-95 31st CH3 CH3 H -OCHz-CcHíCHafp) 120 32nd CH3 CH3 H -OCH 2 -C ₆ H ₄ OCH 3 (p) 128-131

B) Formulation Examples

a) A powder is obtained by mixing 10 parts by weight of the active compound of Example 1 with 90 parts by weight of talc or inert material and grinding it in a hammer mill.

b) A readily water-dispersible wettable powder is obtained by mixing 25 parts by weight of the compound of Example 3 with 64 parts by weight of kaolin-containing quartz, 10 parts by weight of lignin-sulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid and grinding the mixture.

c) An easily dispersible water dispersible concentrate is obtained by mixing 20 parts by weight of the active ingredient of Example 1 with 6 parts by weight of alkylphenol polyglycol ether (Triton X. 207), 3 parts by weight of isotridecanol polyglycol ether (8 AeO) and 71 parts by weight. -Mineral oil (boiling range about 255-377 ° C) and ball mill to less than 5 u.

d) An emulsifiable concentrate is obtained from 15 parts by weight of the compound of Example 3, by parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol (10 AeO) as emulsifier.

e) A spray powder is obtained when 50 parts by weight

The compound of Example 3 was intensively mixed with 20 parts by weight of sodium lauryl sulphate and 10 parts by weight of a condensation product of formaldehyde, cresols and Schaffer's salt, dispersant, 10 parts of sodium sulphate and 10 parts by weight of synthetic precipitated silica.

Cj Biological Examples

Example 1

Weed seeds or tubers are planted in sandy clay soil in 9 cm diameter plastic pots and grown in a greenhouse for 3-5 weeks under good growing conditions. Subsequently, formulations of the compounds of the present invention in the form of a spray powder (e.g. formulation example (b)) or an aqueous solution are sprayed onto the above-ground parts of the plant in an aqueous suspension or spray liquid. The amount of water used is 600-800 liters / ha (at a dose of 10 kg / ha this corresponds to 1.5% of the active ingredient). After about 3 weeks of standstill, the herbicidal effect was evaluated visually in the greenhouse under optimal growth conditions. Table 1 shows the experimental results for the new active substances.

The following rating scale was used:

0 = no effect

1 = 0-20% effect

2- 20-40% effect

3 = 40-60% effect

4 = 60-80% effect 15

5 = 80-100% effect

The values in Table 1 clearly show good herbicidal activity against a broad spectrum of economically important weeds.

Abbreviations used in Table 1:

SIA = Sinapis arvensis

AMR = Amaranthus relroflexüs

STM = Stellaria Media

AS = Avena sativa

ECG = Echinochloa crus-galli

LOM = Lolium multiflorum

a.i. = Active ingredient

Table 1

Post-emergent Herbicidal Effect

Example Number Dosage / ha SIA AMR

Herbicidal effect

STM AS ECG LOM

6th 10 5 3 12th 10 5 5 First 10 5 ' 5 Third 10 5 5 4a. 10 5 5 Second 10 5 5 4b. 10 5 5 21st 2.5 5 5 22nd 2.5 5 5 23rd 2.5 5 4 24th 2.5 4 5 25th 2.5 5 4 26th 2.5 5 4 27th 2.5 4 5 28th 2.5 5 5 29th 2.5 5 5 30th 2.5 4 3 31st 2.5 4 5 32nd 2.5 5 4 Example 2 Sugar cane plants outdoors < experimental compounds are different concentration-

5 3 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 2 4 4 5 1 4 4 5 5 5 5 5 4 5 5 4 3 5 4 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 3 2 4 5 4 5 5 5 4 4 5 5 containment determining the content of cane sugar by known method performed. The origin outcomes together: 2. table reserved

sprayed with aqueous suspensions of emulsifiable concentrates. An emulsifiable concentrate was obtained from 15 parts by weight of the compound of Example 3, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of oxyethylated nonylphenol (10 AeO) as an emulsifier. After 4-8 weeks, the plants were harvested and tested for their raw sugar, i.e. sucrose content (by the so-called .pres's breasts, T. Tanimoto, Hawaiian Planters record 57, 133 (1964)).

Sugar content was determined polarimetrically and was expressed as percentage of cane pol. This number corresponds to the percentage of sucrose in the solution, provided that sucrose is the only substance in the sugar solution that rotates the plane of polarized light. The percentage of reed pol

spreadsheet application sucrose reed pol% quantity content agent the treatment kg / ha after 4 weeks 8 weeks Compound 1 Example I 2.5 II. compound 13.9 14.8 Example 14 2.5 control 12.4 13.3 (Untreated) 10.0 11.2

The active ingredient concentration is 0.37%.

Comparative testing was performed according to ^e> 'Test Example 1.

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1G

Table 3

Eg. song Application rate (kg / ha) (0.05%, 0.1%, 0.2%) Herbicidal effect Post merger application AVF ALM CHS SIA 4c 1.2 / 0.6 / 0.3 (kg / ha) 5/4/3 5/5/3 5/5/3 5/5/5 4d 1.2 / 0.6 / 0.3 (kg / ha) 4/4/2 5/5/2 5/5/3 5/5/5 juice 1.2 / 0.6 / 0.3 (kg / ha) 5/5/3 5/5/3 5/4/4 5/5/5 4f 1.2 / 0.6 / 0.3 (kg / ha) 5/4/3 5/5/3 5/4/4 5/5/5 4g 1.2 / 0.6 / 0.3 (kg / ha) 4/4/3 5/5/3 5/4/3 5/5/5 4h 1.2 / 0.6 / 0.3 (kg / ha) 5/3/2 5/5/3 5/5/4 5/5/5 4i 1.2 / 0.6 / 0.3 (kg / ha) 5/4/2 5/5/2 5/5/2 5/5/4 4k 1.2 / 0.6 / 0.3 (kg / ha) 5/4/2 5/5/2 5/4/3 5/5/4 41 1.2 / 0.6 / 0.3 (kg / ha) 5/4/3 5/5/3 5/4/3 5/5/5 4m 1.2 / 0.6 / 0.3 (kg / ha) 5/4/3 5/5/3 5/3/3 5/5/5 4N 1.2 / 0.6 / 0.3 (kg / ha) 5/4/3 5/5/3 5/5/3 5/5/5 4o 1.2 / 0.6 / 0.3 (kg / ha) 5/3/2 5/5/2 5/4/3 5/5/4 4p 1.2 / 0.6 / 0.3 (kg / ha) 5/4/2 5/5/2 5/4/3 5/5/5 4q 1.2 / 0.6 / 0.3 (kg / ha) 5/4/2 5/4/2 5/4/3 5/4/4 4r 1.2 / 0.6 / 0.3 (kg / ha) 5/3/2 5/3/1 5/5/4 5/5/4 4s 1.2 / 0.6 / 0.3 (kg / ha) 5/4/2 5/5/2 5/5/4 5/5/5 4t 1.2 / 0.6 / 0.3 (kg / ha) 4/3/3 5/5/3 5/4/4 5/5/5 4u 1.2 / 0.6 / 0.3 (kg / ha) 4/3/3 5/5/3 5/4 / - 5/5/4 4v 1.2 / 0.6 / 0.3 (kg / ha) 5/4/2 5/5/2 5/5/4 5/5/4 4w 1.2 / 0.6 / 0.3 (kg / ha) 5/3/1 5/5/2 5/4/3 5/5/4 4x 1.2 / 0.6 / 0.3 (kg / ha) 4/3/2 5/4/2 5/3/3 5/5/5 4y 1.2 / 0.6 / 0.3 (kg / ha) 4/3/2 5/4/1 5/4/3 5/4/3 4Z 1.2 / 0.6 / 0.3 (kg / ha) 5/3/2 5/5/2 5/5/3 5/5/5 4a? 1.2 / 0.6 / 0.3 (kg / ha) 4/3/1 5/4/1 5/4/3 5/5/5 4 ab 1.2 / 0.6 / 0.3 (kg / ha) 5/3/3 5/5/3 4/4/4 5/5/4 4 Ac 1.2 / 0.6 / 0.3 (kg / ha) 4/3/2 5/5/3 5/4/4 5/5/4 4AD 1.2 / 0.6 / 0.3 (kg / ha) 5/3/3 5/4/2 5/4/4 5/5/4 4AE 1.2 / 0.6 / 0.3 (kg / ha) 5/3/2 5/4/2 5/4/3 5/5/5 4AF 1.2 / 0.6 / 0.3 (kg / ha) 4/4/2 5/5/4 5/4/4 5/5/5 4AG 1.2 / 0.6 / 0.3 (kg / ha) 5/4/2 5/5/3 5/5/4 5/5/5 4 ah 1.2 / 0.6 / 0.3 (kg / ha) 5/3/2 5/5/4 5/4/3 5/5/5 4 Al 1.2 / 0.6 / 0.3 (kg / ha) 4/3/2 5/5/2 5/4/4 5/5/5 4ak 1.2 / 0.6 / 0.3 (kg / ha) 4/3/2 5/4/2 5/4/4 5/5/5 4AL 1.2 / 0.6 / 0.3 (kg / ha) 5/3/2 5/5/3 5/5/4 5/5/5 4am 1.2 / 0.6 / 0.3 (kg / ha) 5/4/2 5/5/4 5/5/5 5/5/5 1 2.5 / 0.6 kg / ha - / - - / - 5/5 5/5 2 2.5 / 0.6 kg / ha - / - 5/5 5/5 3 2.5 / 0.6 kg / ha - / - - / - 5/5 5/5 4b 2.5 / 0.6 kg / ha - / - - / - 5/5 5/4 4an 2.5 / 0.6 kg / ha - / - - / - 5/4 5/5 4ao 2.5 / 0.6 kg / ha - / - - / - 5/5 5/5

Comparative compound

Vi 5 / 2.5 / 1.2 / 0.6 kg / ha 4/2/1/0 - 4/2/0/0 4/3/1/0 vz 5 / 2.5 / 1.2 / 0.6 kg / ha - / 1/0/0 - / 1/0/0 2/1/0/0 5/2/1/0

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abbreviations:

AV - Avena Fatuna

ALM - Alopecurus gingivitis CRS - Chrysantemum segetum (sowing golden flowers)

SIA - Sinapis arvensis (vadrepce)

Impact in scores:

0 = Tea effect 1 = 0-20% effect

2 = 20-40% effect 3 = 40-60% effect 4 = 60-80% effect 5 = 80-100% effect

Vi = Ν, Ν-bis (phosphonomethylglycine) (see U.S. Patent No. 3,556,762).

V2 = ammonium ethylcarbamoyl phosphonate (see U.S. Patent No. 3,627,557).

0 n

H5C2O-P-C NH2

Claims (4)

PATENT CLAIMS CLAIMS 1. A herbicidal and growth regulator composition comprising 0.03-60% by weight of a compound of formula (I) R 1 and R 2 each independently represent the same or different C 1-2 alkyl groups; R 3 is -OH, C 1 -C 10 alkoxy, phenoxy, benzyloxy, halobenzyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 alkenyloxy, C 1 -C 4 alkylbenzyloxy, C 1 -C 4 alkoxybenzyloxy or hydrazino; R4 is hydrogen or CO-NR8Re wherein R5 is hydrogen and Re is selected from the group consisting of C3-C6 alkylsulfonyl monosubstituted with halogen and their base salts thereof with conventional solid carriers, preferably quartz, talc or liquid carriers, preferably an organic solvent, water or mineral oil, optionally with a surfactant, preferably an anionic or nonionic surfactant. The composition of claim 1 Characterized in that it contains as an active ingredient a compound of the formula I in which R1 and R2 are methyl, R4 is hydrogen, R3 is hydroxy or C1-C6 alkoxy; R3 is a salt of an inorganic or organic base when R3 is hydroxy. 3. The composition of claim 1 wherein the active ingredient is 2- (di- Contains 15 methylphosphinoyl) -2-hydroxyacetic acid, its methyl ester and its ammonium and C1-C4 alkylammonium salts. 4. A process for the preparation of a compound of formula I and optionally base salts thereof 20 - where R 1 and R 2 each independently represent the same or different C 1 -C 2 alkyl, phenyl, benzyl or hydroxy groups, R3 is hydroxy, C1-C10 alkoxy, amino or hydrazino, benzyloxy, halobenzyloxy, C2-C4 alkynyloxy, C2-C4 alkenyloxy, phenoxy, C1-C4 alkyl benzyloxy, C 1-4 alkoxybenzyloxy; R4 is hydrogen or CONR5Rg wherein R8 is hydrogen and Rg is C 1-4 alkyl optionally substituted with C 1-4 alkoxy or C 1-4 alkoxycarbonyl, C 3-6 alkyl substituted with halogen, C 1-6 sulfonyl, C 3-6 alkenylsulfonyl, halo-substituted phenyl, characterized in that a) reacting a compound of formula II wherein R 1 and R 2 are as defined above, with a compound of formula III wherein Π 3 is as above, to form compounds of formula II wherein R 4 is H; or * b) for the preparation of compounds of formula (IV) wherein R4, R2 and R3 are other than H, where R, R2 and R3 are as defined above, in a known manner, acylating and optionally converting the acids to their salts in a manner known per se.