Cyclohexanedione-carboxylic-acid derivatives having a herbicidal and plant growth regulating activity.

wherein A represents a radical -OR₂ or -NR3R4, B is hydroxyl, a residue - NIIORj or a metal or ammonium salt thereof, R is Cx-Ce-alkyl or C₃-C_e-cycloalkyl, unsubstituted or substituted by halogen, € 4 -C₄-alkoxy or C_x- C₄-alkylthio, R_x is C₁- C₆-alkyl, C_x-C₆-halogenalkyl, C₃-C₆25 alkenyl, C₃ -C₆-halogenalkenyl or C₃ - C₆-alkynyl, R₂, R₃ and R₄ represents independently of each other hydrogen; C_x-C₆-alchiI, Cj— C₆-halogenalkyl, C₂-C₁₀-alkoxyalkyl, C₂-C₁₀-alchiltioalchil; C₃ -C₆-alkenyl, not substituted or substituted by halogen, C_x —

LEI PRICE 31.00

C₄-alkoxy or C₄ -C₄-alkylthio; C₃ -C₆- alkynyl; phenyl, wherein the phenyl ring is unsubstituted or substituted by halogen, C_t- C₄-alchiI, Cj — C₄-alcoxy, C₁- C₄-haHogenogenalkyl, nitro or cyan; R₃ and R₄ together with the nitrogen atom to which they are linked, they also form a 5- to 6-membered heterocycle, which may also contain an oxygen or sulfur atom in the ring; from 3 to 10% by weight of an active surfactant selected from Na ligninsulfonate, laurylsulfonate and / or diisobutyl-naphthalene-sulfonate; 2 ... 5% by weight of a dispersing agent selected from octylphenolpolyethylene glycol, carboxymethylcellulose and polyethylene glycol, as well as 60 ... 95% from a carrier between talc, silicic acid, kaolin and / or sodium chloride.

4 examples of embodiments of the invention are given below.

Example! 1. Prepare for active substances of formula I (% = weight percent):

Spray powder a) b) c) - active substance 20% 60% 0.5% - sodium lignin sulphonate

5% 5% 5% - sodium lauryl sulfonate:

3% - - Sodium diisobutylnaphthalene

- 6% 6% - octylphenolpolyethylene glycol (7-8 mole ethylene oxide) - 2% 2% - highly dispersed silica

5% 27% 27% - kaolin 67% - - - sodium chloride - - 59.5%

The active substance mixes well with the additives and grinds well into a suitable mill. Sprinkler powders are obtained which can be diluted with water giving suspensions of any desired concentration.

<td colspan="3">Example 2</td>

<td>c) Powdering agents</td><td></td><td>b)</td>

<td>- active substance</td><td> 0,1%</td><td> 1%</td>

<td>- kaolin</td><td> —</td><td> 99%</td>

<td>- talc</td><td> 99,9%</td><td> —</td>

Ready-to-use powdering agents are obtained by mixing the active substance with the support material and grinding on a

<td colspan="3">suitable mill.</td>

<td>Example 3</td><td></td><td></td>

<td>Extruded granulate</td><td>a)</td><td>b)</td>

<td>- active substance</td><td> 10%</td><td> 1%</td>

<td>- sodium lignin sulphonate</td><td> 2%</td><td> 2%</td>

<td>- Carboxymethylcellulose</td><td> 1%</td><td> 1%</td>

<td>- kaolin</td><td> 87%</td><td> 96%</td>

<td colspan="2">The active substance is mixed with</td><td>mate-</td>

¹⁵ add rials, grind and moisten with water. This mixture is extruded and then dried in a stream of air.

Example 4

Pellet granulate a) - active substance 3% - polyethylene glycol (molecular weight ₂₅ 200) 3% - kaolin 94%

The finely milled active substance is applied evenly in a kaolinnri mixer _3Q moistened with polyethylene glycol. In this way granules with dust-free coating are obtained.

The method of applying the above compositions is shown in the following examples:

a) Herbicidal action before emergence ³⁵ the plants in the greenhouse resemble seeds of plants id. 11 cm diameter flower pots. Immediately thereafter, the earth's surface becomes

4₀ it treats with an aqueous emulsion of the active substances. A concentration of 4 kg of active substance ha is used. Then the pots are kept in the greenhouse at a temperature of

22 ... 25 ° C and relative humidity of 50 ... 70%. After 3 weeks the test is interpreted and the action on the experience plants is noted according to the following scale: 1 - the plant has not sprouted or is completely dead, 2–3 - very powerful action5q, 4–6 - average action, 7–8 - action weak, 9 - no action (as the control treats us).

The results are given in table 1.

Table 1

<td>The plant</td><td>Oatmeal saliva</td><td>Setaria italica</td><td>Sinapis alba</td><td>Stellar average</td>

<td>Active substance 2.37</td><td> 1</td><td> 1</td><td> 9</td><td> 9</td>

<td> 2.47</td><td> 1</td><td> 1</td><td>υ</td><td> 9</td>

<td> 2.61</td><td> 1</td><td> 1</td><td> 9</td><td> 9</td>

<td> 2.63</td><td> 3</td><td> 1</td><td> 9</td><td> 9</td>

<td> 2.64</td><td> 1</td><td> : -² .</td><td> 8</td><td> 8 '</td>

b) Herbicidal action when applying the active substances after the emergence of plants

The different crops and weeds are grown from seeds in pots in the greenhouse until they reach the stage of 4 to 6 leaves. Then, the plants are sprayed with aqueous emulsions of the active substance (obtained from the 25% emulsion concentrate) in a dosage of 4 kg / ha. The treated plants are then kept under optimal conditions of light, regular watering, temperature of 22, .. 25 ° C and relative atmospheric humidity of 50 ... 70%. The interpretation of the test is done 15 days after the treatment according to the above scoring scheme with the results presented in table 2. '

Table 2

<td></td><td>The plant</td><td>Avena saliva</td><td>Setaria Italic</td><td>Lolium Perennial</td><td>Solanum lycopersicum</td><td>sinapis white</td><td>Slellaria mediate</td><td>Phaseolus luyaris</td>

<td>Substance 2.37</td><td>activate</td><td> 1</td><td> 2</td><td> 2</td><td> 9</td><td> ' 8</td><td> 8</td><td> 7-</td>

<td> 2.47</td><td></td><td> 2</td><td> 4</td><td> 2</td><td> 4</td><td> 6</td><td> 8</td><td> 9</td>

<td> 2.61</td><td></td><td> 1</td><td> 2</td><td> 2</td><td> 7</td><td> 7,</td><td> 8</td><td> .9</td>

<td> 2.63</td><td></td><td> 1</td><td> 1</td><td> 2</td><td> 8</td><td> 5</td><td> 8</td><td> 5</td>

<td> 2.64</td><td></td><td> 1</td><td> 1</td><td> 2</td><td> 4</td><td> 7</td><td> 8</td><td> 9</td>

c) Inhibition of growth in tropical cover legumes

The experimental plants (Centrosema plumierii and Controsema pubescens) are cultivated until the stage of complete development and then shortened by cutting to a height of 60 cm. After 7 days, the active substance is sprayed as an aqueous emulsion. The experimental plants are kept at a relative atmospheric humidity of 70% and 6000 lux artificial light, 14 hours a day, at temperatures of 27 ° C during the day and 21 ° G during the night. 4 weeks after application the test is interpreted. For this, the growth again is compared in the control and the phytotoxicity is weighed and noted. In this test, plants treated with the active substances of formula I show a pronounced reduction of growth again (less than 20% growth again in untreated control plants), without thereby attacking experimental plants.

d) Adjusting the growth of soy beans in plastic vessels with a mixture of soil - peat - sand in a ratio of 6: 1 soybeans are sown and kept in an air-conditioned room. By optimum choice of temperature, illumination, addition of fertilizers and watering, the plants develop after about 5 weeks until the stage of 5 ... 6 leaves trifolia. At this point, the plants are sprayed with an aqueous solution of an active substance of formula I until well watered. The concentration of active substance reaches' up to 100 g / L, the interpretation is done about 5 weeks after the application of the active substance. In comparison with untreated consumption plants, the active substances of formula I, according to the present invention, cause a remarkable increase in the number and weight of the pods in the main strain.

e) Inhibition of growth at what; pans in plastic pots with sterilized earth kept in the greenhouse, resemble the Hordeum vulgare (spring barley) and Secale (spring rye) cereals and water as needed: The seedlings sprinkle about 21 days after sowing with the solution of aqueous spray of an active substance of formula I. The amount of active substance is up to 100 g of active substance per hectare. 21 days after application the growth of cereal is noted. The treated plants show in comparison with the untreated controls a decrease of the growth again (60 ... 90% of the control), as well as partly an increase of the diameter of the stem.

⁴⁰

f) Inhibition of the growth of grasses in plastic capsules with soil-peat-sand mixture (6: 3: 1) kept in the greenhouse, resembling Lolium perenne herbs, • 45 Poa pratensis, Festuca ovina, Dactglis glomerate and Cynodon dactylon and water as needed. The emergent herbs are cut weekly up to the height of 4 cm and about 50 days after sowing and 1 day after the last cutting they are sprayed with the aqueous spray solution of an active substance of formula I. The amount of active substance is recalculated up to 100 g of active substance per ha. 21 days after application, weed growth 55 is estimated. ' The investigated compounds cause a reduction in growth again by

10 ... 30% compared to the untreated control.

When using small quantities applied, the compounds of formula I are characterized by good selective properties of growth inhibition and selectively - herbicides that make them ideally suitable for use in useful plant crops, especially sugar cane, cereals , cotton, soy, corn and rice. In this case, weeds are attacked, which until now could only be attacked with total herbicides.

The mode of action of these active substances is unusual. Many of them are translatable, meaning they are taken by the plant and transported to other places where they begin to act. Thus, it is possible, for example, that by surface treatment the perennial weeds are attacked to the roots. The compounds of formula I work in very small quantities compared to other herbicidal compounds and growth regulators.

In addition, compounds of formula I have strong regulatory properties for plant growth which can be evidenced by an increase in crop yields or cereals. Many compounds of formula I also present an action to prevent the growth of plants depending on the concentration. Both monocotyledons and dicotyledons are affected in their growth.

Thus, for example, legumes grown in agriculture in tropical regions are often selectively hampered in their growth by compounds of formula I, so that soil erosion is actually prevented by crop plants, but "eover erops" cannot. to compete with culture.

An inhibition of vegetative growth allows for many crop plants a denser cultivation of the crop so that a larger crop can be obtained relative to the soil surface. Another mechanism of crop growth with growth inhibitors is based on the fact that nutrients to a greater extent help flower and fruit formation, while vegetative growth is limited.

In monocotyledonous plants, for example, herbs and / or cereal crops, it is sometimes desirable and advantageous for an inhibition of_; vegetative growth. Such growth inhibition is among others of economic interest in grasses, because, for example, it is possible to reduce the frequency of grass clippings in gardens, parks and sports fields or roadside. Importantly sc also shows the inhibition of growth in plants of the cabbage category and in woody plants on the roadside and near the electricity transmission lines or in general, in regions where strong growth is undesirable.

Important is the use of growth regulators to inhibit the growth in length in cereals, because by shortening the straws reduce or remove, completely the danger of breaking the plants before harvesting. Apart from this, growth regulators can determine in the grain a strengthening of the straw, which also opposes breaking. Also, (Compounds of formula I can be successfully used to prevent potato sprouting from stock. In potatoes it often develops in storage during winter sprouts that result in wrinkling, weight loss and rot.

in the case of large amounts of mat application, all the tested plants are attacked in their development as they are damaged.

The present invention relates to herbicides and plant growth regulators containing an active substance of formula I as well as to processes for pre-emergent and post-emergent weed control and for inhibiting plant growth in monocotyledonous and dicotyledonous plants, especially tropical grasses. soil and tobacco branches.

The compounds of formula I are used in an unmodified form or, preferably, as agents together with the usual auxiliary substances in the formulation technique and for this purpose they process, as known, for example, spraying powders, soluble powders, powdering agents, granulates , as well as encapsulations in, for example, polymeric substances. Methods of application such as spraying, blurring, powdering, spreading, or pouring, are suitably chosen, as well as the type of agents, for the purposes pursued and the conditions given.

The formulations, that is, agents containing the active substance of formula I, possibly a solid additive, the preparations or compositions are prepared in the known manner, for example, by intimately mixing and / or grinding the active substances with dilution agents such as, for example, with solvents, solid support materials and, possibly, surfactants (surfactants).

As solid support materials, for example, for powdering agents and dispersible powders, natural flours of rock with talc, calcite, kaolin, montmoriîonite or attapulgite are usually used. Silica can also be added to improve the physical properties^: High dispersed hinged polymer high dispersed absorbent. As adsorbent granular support materials, porous types such as pumice stone, bricks crack, sepiolite or bentonite can be considered, as non-absorbent support materials, for example, calcite or sand, in addition a multiple of inorganic or organic prepranulated materials, in particular dolomite or milled residues of plants.

As surfactants, depending on the type of active substance of formula I to be formulated, non-ionic surfactants, cations and / or active anions with good emulsifying, dispersing and wetting properties are considered. By tensides we will also mean mixtures of tensides. Suitable anionic surfactants can be so-called water-soluble soaps and water-soluble synthetic surfactants.

As soaps can be mentioned alkaline, alkaline-earthy or ammonium salts, possibly substituted by higher fatty acids (C₁₀... C_z3) such as, for example, sodium or potassium salts of oleic or stearic acid, or mixtures of natural fatty acids which can be obtained, for example, from coconut oil or soybean oil. Mention may also be made of methyl taurine salts of fatty acids. Additives are used, however, called synthetic surfactants, in particular fatty sulphonates, fatty sulphates, derivatives of benzimidazole sulphonates or alkylarylsulfonates. Fat sulfates or sulfates are usually alkali, alkaline earth or ammonium salts, possibly substituted and have an alkyl radical with 8 to 22 carbon atoms, in which case alkyl also includes the alkyl part of acyl radicals, for example, sodium or calcium salt of ligninsulfonic acid, dodecylsulfuric acid ester or a mixture of fatty alcohol sulphate prepared from natural fatty acids. This also includes the salts of sulfuric acid esters and sulfonic acids of fatty alcohol and ethylene oxide adducts. The sulphonated benzimidazole derivatives preferably contain 2-sulfonic acid groups and an 8- to 22-carbon fatty acid radical. Alkylarylsulfonates are, for example, sodium, calcium or trietanoamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalinsulic acid, or a condensation product of naphthalenesulfonic acid and formaldehyde.

Suitable sulphates such as, for example, the phosphoric acid ester salts of a p-nonylphenol- (4-14) -ethylene oxide and isofolipide adduct may be considered.

As nonionic surfactants, one may consider, first of all, derivatives of polyglycololeters of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and phenyl acyls which may contain 3 to 30 groups of glycolether and 8 to 20 carbon atoms in the radical. hydrocarbon (aliphatic) and 6 to 18 carbon atoms in the alkyl radical of the alkylenols.

Other suitable nonionic surfactants are polyethylene glycol water soluble polypropylene glycols containing 20 to 250 groups of ethylene glycol ethers and 10 to 100 groups of propylene glycol ethers, ethylene diamines polypropylene glycol and alkyl polypropylene glycol in 1 to 10 carbon atoms. Said compounds usually contain per unit of propylene glycol 1 to 5 units of ethylene glycol.

Examples of nonionic surfactants include nonylenolpolyethoxyethanol, castor oil polyglycols, polypropylene polyethylene oxide adducts, tributylphenoxypolyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Also, polyoxyethylensorbitan fatty acid esters such as the polyoxyethylensorbitan trioleate may be considered.

In cationic surfactants, it is mainly quaternary ammonium salts which contain as N-substituents at least one alkyl radical with 8 to 22 carbon atoms and as other substituents have lower hydroxyalkyl radicals, lower alkyl, benzyl or hydroxyalkyl radicals, optionally halogenated. . The salts are preferably found as halides, methylsulphates or ethylsulphates, for example, stearyltrimethylammonium chloride or benzyl- (2-chloroethyl) - ethylammonium bromide. Voltages used in the formulation technique are described among others in the following publications: "Mc Cufcheon's Detergents and Emulsifiers Annual" MC Publishing Corp, Ridgewood New Jersey, 1979; J and M.Ash., “Encgclopedia of Surfactans you. I — III, Chemical Publishing Co., Inc .. New York, 1980/81.

Preparations of active substance usually contain 0.1 to 95%, in particular 0.1 to 80%, active substance of formula 1.1 to 99.9% of a solid or liquid additive and 0 to 25%, in particular 0.1. Get 25% of a stress.

In particular, the preferred formulations have the following composition (% = weight percent):

powders:

- active substance ............ 0.1 to 10% preferably, 0.1 to 1%;

- solid support material ..................

99.9 takes 90%, preferably 99.9 to 99%;

Wettable powders - active substance ........................

0.5 to 90%, preferably 1 to 80%;

- surfactant ........................

0.5 to 20%, preferably 1 to 15%;

- solid support material ...............

to 95%, preferably 15 to 90%;

Granulated is:

- active substance ........................

0.5 to 30%, preferably 3 to 15%;

- solid support material ..................

• 99.5 to 70%, preferably 971 to 85%.

While as a commercial agent a concentrated agent is preferred, the final consumer usually uses dilute agents. The application forms can be diluted up to 0.001% active substance. The applied quantities usually include 0.001 at 10 kg / ha, preferably 0.025 at 5 kg / ha.

Agents may also contain such additions, as foam stabilizers, viscosity regulators, binders, adhesion agents as well as fertilizers or other active substances for special effects.

The invention has the advantage of leading to the obtaining of herbicidal compositions which have at the same time strong regulatory properties of plant growth, which leads to the increase of the crop plant crops.