CS197321B2 - Means for regulation of the plants growth - Google Patents

Abstract

Substituted isoxazolylbenzoates of the formula: <IMAGE> are previously unknown active compounds for regulating the growth or the development of desired or unwanted plants. They can be employed pre-emergence or post-emergence in a conventional manner. In the formula, A and B have the meanings given in Claim 1.

Description

The invention relates to novel isoxazol-5-yl-benzoates and isoxazol-3-yl-benzoates as well as their use as agricultural chemicals. The novel compounds are effective in suppressing the growth of unwanted vegetation. At smaller doses, the compounds are effective in controlling the growth of unwanted plants.

The compounds of the invention have the following chemical formula

(CF ₃ ) '

i h jt Ohe.bolja.

Isoxazol-5-yl-benzoates according to the invention are prepared by reacting the corresponding hydroxamoyl chloride with o-vinyl benzoate under basic conditions (such as in the presence of tertiary R denotes a hydrogen atom, a lower alkyl group or an agriculturally acceptable cation). is 0.

amine amines) to form isoxazolin-5-yl-benzoate, which can then be converted to isoxazol-5-yl-benzoate by heating with N-bromo succinimide or dichlorodicyanezoquinone. For clarity, the following reaction scheme is given:

(1) Aryl-CHO

CZH _S OH

Cl & (CHCl ₃ n * bo

NOCI) α.th < ^r (// DAr / 1-CNOH * fYC ⁾

Hab Θ Habo DD & CCltf.

Δ

It will be appreciated by those skilled in the art that the corresponding hydroxamoyl chloride is prepared according to the above scheme by reacting hydroxylamine with arylaldehyde in an aqueous alcohol solution to give compound II, which can then be chlorinated to hydroxamoyl chloride (III).

Arylaldehydes can be prepared according to the method of Jolad and Rajagopala, Org. · Son. Coll., V, page 139 (1973). The o-vinyl benzoate can be prepared by reacting vinyl benzoic acid with thionyl chloride and then with an alcohol. o-Vinylbenzoic acid can be prepared according to the following examples, which are given to illustrate the above process.

Example 1

Production of o-vinylbenzoic acid.

The sodium salt of 2-carboxybenzaldehyde is prepared by adding 129.6 g (0.60 mol) of 25% sodium methoxide in methanol to a solution of 90 g (0.6 mol) of 2-carboxybezaldehyde in 900 ml of methanol followed by concentration at 90 degrees Celsius and pressure 66,7 Pa.

Methylenetrifenylphosphorane is prepared on a 0.605 molar scale in dimethylsulfoxide from methyltriphenylphosphonium bromide and dimethylsodium as described in E.J. Corey et al.,

J. Org. Chem., Vol. 28, p. 1128 (1963). Sodium carboxylate is then added under stirring under a nitrogen atmosphere. After a few minutes, the solution was concentrated under vacuum from an oil pump (maximum bath temperature of 45 ° C) and water was added to the residue. The mixture was filtered and 57 ml of concentrated hydrochloric acid was added with stirring. The resulting mixture was extracted with ether. The ether solution was extracted with 5% sodium hydroxide. The aqueous layer was acidified with hydrochloric acid and then extracted with ether. The ether solution was dried and concentrated in vacuo to g (69%) of a sticky solid. A small portion was recrystallized from degassed ether to give 1.5 g of solid, mp 89-90 ° C.

Example 1 a d 2

Production of methyl o-vinyl benzoate.

A mixture of 58.5 g (0.395 mol) of o-vinylbenzoic acid and 127.3 g (1.08 mol) of thionyl chloride is heated on a steam bath (vigorous gas evolution) for 40 minutes until gas evolution ceases. The solution is concentrated and 270 ml of methanol are slowly added. The mixture is kept under reflux for 10 minutes and then concentrated. Ether was added to the residue and the solution was then extracted three times with water. The ether layer was dried and some hydroquinone was added and the solution was distilled to give 32.2 g (50.5%) of a liquid, mp 64-78 ° C.

Example 3

Preparation of methyl 1-2- (3- (3- (trifluoromethyl) phenyl) -5-isoxazolyl) benzoate.

A solution of 8.67 g (0.0858 mol) of triethylamine in 25 ml of ether was added dropwise and with stirring to a solution of 19.19 g (0.0858 mol) of m-trifluoromethylbenzo) hydroxamoyl chloride and 13.9 g ( 0.0858 mol) of methyl o-vinylbenzoate in 200 ml of ether at 0 to 5 ° C over 45 minutes. The mixture was stirred in an ice bath for 2 hours and then at 20 ° C for 21 hours and then washed three times with water. The ether layer is filtered to. a little gelatinous solid is removed, the filtrate is dried (calcium sulphate) and concentrated in vacuo at 60 ° C to give 29.5 g (98%) of methyl- [2- [β (; (trifluoromethyl) phenyl] -2-isoxazolin-5-yl] benzoate.

A solution of 26.74 g [0.0766 mole] of isoxazoline prepared above and 13.6 g (0.0766 mole) of N-bromosuccinimide in 250 ml of carbon tetrachloride is heated under reflux with stirring for 10-15 minutes after the addition of 0. 5 g of benzoyl peroxide is evident in the red color of bromine After heating the reaction mixture under reflux for 1 hour, 0.1 g of benzoyl peroxide is added and heating is continued for an additional hour The reaction mixture is cooled and filtered to separate from succinimide. It is concentrated under vacuum and the residual oil is subjected to a KugehOhr distillation at 140 to 170 ° C (26.7 Pa), and when the boiler temperature reaches 140 ° C, a temporary vacuum reduction to 133 to 267 Pa and an acidic The distillate was further distilled according to Kuge.roro to give 20.01 g of 98% pure product as a viscous oil Crystallization of the oil from an ether / hexane mixture at 0 ° C gave. 13.86 g solid, mp 46.5-48.5 dc;

AND

For C18H12F3NO3 · Calculated: C 62.25, H 3.48, N 4.03.

Found:% C, 62.33;% H, 3.49;% N, 4.09.

Acids may be prepared by hydrolysis of the corresponding ester. Salts. se. they can be prepared by reacting the appropriate base with the free acid.

Example 1 a d 4 ·

Preparation of 2- (3- (3-trifluoromethylphenyl) -5-isoxazolyl) benzoic acid A solution of 6.20 g methyl 2- [3- (3-trifluoromethylphenyl) -5-isoxazolyl] benzoate, 75 ml acetic acid and 50 ml concentrated hydrochloric acid was heated under reflux for 4 hours, cooled, poured into 450 ml of cold water. The resulting solid was crystallized from acetonitrile to give 3.87 g solid, mp 176-177 ^o C. ·

For C17H10F3NO3.

calculated ·: 61.27%. C, 3.02% H, found: 61.25%. C, 3.03 ·% H,

Isoxazol-3-yl-benzoates can be prepared as follows:

«Jccton

CO, ^R> Water CHO CH ^ OH

I WANT.

CH = NOOH

CO ^ R

C-NOH 1

CL

Those skilled in the art will recognize that. o-formylbenzoates can be prepared by known methods. Addition of hydroxylamine hydrochloride in aqueous methanol yields 2- (hydroxyiminomethyl) benzoates, which can be converted to the corresponding benzohydroxamoyl chloride esters by addition of chlorine in chloroform. by reaction with N-bromosuccinimide or dichlorodicyanobenzoquinone.

Example 5

Production of o-methoxycarbonylbenzohydroxamoyl chloride. Methyl iso -benzoate was prepared in 81% yield from. 2-carboxybenzaldehyde following the procedure of Br-own and Sargent, Journal Chemical Society, p. 1818 (1969). A solution of 1.64 g (0.010 mol) of methyl o-formylbenzoate and 1.05 g (0.015 mol) of hydroxylamine hydrochloride in 95 ml of 30% aqueous methanol is stirred at 23 ° C for 50 minutes and then cooled. Friction of the wall causes crystallization of 0.70 g of a white solid (m.p. 73-74.5 ° C) which is methyl 2- (hydroxyiminomethyl) benzoate.

Do ·. of a solution of 7.87 g (0.0439 mol) of methyl 2- (hydroxyimethylphenyl) benzoate in 250 ml of chloroform stirred at 0 DEG C. (ice / methanol bath) is slowly bubbled through. The solution turns blue and the clear solution becomes cloudy After a few minutes the blue reaction mixture turns green After about 20 minutes the excess chlorine begins to pass through the solution, so the addition of chlorine is stopped and the solution is stirred in an ice bath. after 1 hour until the green color almost fades · Nitrogen is bubbled through the solution and the solution is allowed to warm to 20 ° C for · 30 minutes The solution is concentrated under vacuum at 30 to 40 ° C. · Ml · ether, the supernatant is decanted off from some insoluble resin and concentrated to 7.21 g of a viscous cleft.

197 was identified as o-methoxycarbonylbenzohydroxamoyl chloride.

Example 1 a d 6

Preparation of methyl 2- [5- (3-trifluoromethyl) phenyl-3-isoxazolyl] benzoate. To a solution of 12.3 g (0.0714 mol) of m-trifluoromethylstyrene and 15.6 g (0.073 mol) of o-methoxycarbonylbenzohydroxamoyl chloride in 200 ml of ether stirred at 0-5 ° C, a solution of 9.43 g (0.073 mol) was added dropwise. of ethyldiisopropylamine in 35 ml of ether over 45 minutes. The mixture was stirred at 0-5 ° C for an additional 2 hours and then at 0 ° C for 3 hours. 50 ml of ether are added and the mixture is extracted three times with 200 ml portions of water. The ether layer was dried (sulfate, calcium) and concentrated in vacuo to a pressure of 66.7 Pa and 90 ° C to give 18.4 g of an oil identified as methyl 2- [5- (3- (trifluoromethyl) phenyl] - 2-Isoxazol-3-yl] -benzoate.

A mixture of 14.2 g (0.0407 mol) of methyl 2- [5- (3- (trifluoromethyl) phenyl] -2-isoxazolin-3-yl] benzoate, 7.26 g (0.0408 mol) of N- bromosuccinimide and 0.3 g of benzoyl peroxide in 150 ml of carbon tetrachloride are heated under reflux for 4 hours, cooled, filtered and concentrated in vacuo to 14.5 g of oil. (13.3 Pa) which was redistilled to give 9.8 g (70%) of 97% pure product at 148 ° C (13.3 Pa).

For C18H12F3NO3.

calculated: 62.25% C, 3.48% H, 4.03% N. found: 62.27% C, 3.50% H, 4.09% N.

Example 7

Preparation of methyl 2- [5- (2-pyridyl) -3-isoxazolyl] benzoate. A solution of 2-vinylpyridine (7.38 g, 0.0702 mol) and ethyldiisopropylamine (9.07 g, 0.0702 mol) in ether (60 ml) was added dropwise to a solution of 150.0 g (0.0702 mol) over a period of 20 minutes. -methoxycarbonylbenzohydroxamoyl chloride in 200 ml of ether stirred at 0-5 ° C. The mixture was stirred at 0 to 5 ^Q C · additional two hours and then at 20 ° C · 24 hours and then the mixture is washed twice with aqueous sodium bicarbonate and once with brine. The ether layer was dried (calcium sulfate) and analyzed by infrared spectroscopy, which showed that some nitriloxide had to be removed. The ether solution was allowed to stand for an additional 48 hours and then concentrated at 90 ° C and 20.0 Pa to give 14.23 g of viscous methyl 2- [5- (2-pyrldyl) -2-isoxazolin-3-yl] ] benzoate.

A mixture of 11.0 g (0.039 mol) of methyl 2- [5- (2-pyridyl) -2-isoxazolin-3-yl] benzoate and 9.76 g (0.043 mol) of 2,3-dichloro-5,6- of dicyano-1,4-benzoquinone in 200 ml of chlorobenzene is kept under reflux for 3 hours; The mixture was cooled, filtered and concentrated in vacuo to a residue of 12.0 g. This residue is chromatographed on

321

400 g of silica gel with 20% ether in benzene gave 3.8 g (35%) of solid, mp 54-57 ° C. Recrystallization of a portion of the sample gives a solid with a melting point of 58-60.5 ° C.

For C16H12N2O3.

C, 68.56; H, 4.32; N, 9.99. Found:% C, 68.41;% H, 4.35;% N, 9.93.

Acids may be prepared by hydrolysis of the corresponding ester.

Example

Preparation of 2- {5- [3- (trifluoromethyl) phenyl] -3-isoxazolyl] benzoic acid. A sample of 9.8 g of methyl 1-2- [5- [-3- (trifluoromethyl) phenyl] -3-isoxazolyl] benzoate in benzene was added. Allow to stand for three days in a column packed with alumina of activity I. Elution of the column with glacial acetic acid gives 15 g of a solid. This solid was added to dilute hydrochloric acid and the solution was extracted with ether. Concentration of the ether gave 3.8 g of a solid which was recrystallized from aqueous ethanol to give 3.0 g of solid, m.p. 165-167 C. ^e

For C17H10F3NO3.

calculated: 61.27% C, 3.02% H, 4.20% N; Found:% C, 61.05;% H, 3.02;% N, 4.24.

Methyl 2- [5- (4-pyridyl) -3-isoxazolyl) benzoate, m.p. 84-85 ° C, was prepared in a manner similar to the procedure described above.

For C16H12N2O3.

calculated: - 68.57% C, 4.32% H; Found: C, 68.43; H, 4.32.

The term "lower alkyl" as used herein means alkyl groups having one to five carbon atoms inclusive.

The term "agriculturally acceptable cations" refers to those cations that are commonly used in agricultural formulations to form the free acid salt and include, but are not limited to, alkali metal cations, substituted amines, and ammonium cations.

As noted above, the compounds of the invention are effective in partially or completely inhibiting undesirable vegetation. Tables I and II summarize the results of the post-stiff tests. determination of pre-emergence and post-emergence herbicidal activity of the compounds.

The pre-emergence test is performed as follows:

The topsoil is placed in aluminum pans and packed to a depth of 0.95 to 1.3 cm from the top of the pan. A preselected number of seeds and vegetative shoots of different plant species are placed on top of the topsoil. The soil needed to cover the seeds or vegetative shoots was weighed into the bowl. A known amount of the active ingredient applied in solution or as a wettable powder is thoroughly mixed with the soil and used as a coating in the prepared trays. The dishes are then placed on a bench in a greenhouse where they are watered from below to provide adequate moisture for germination and growth.

Unless otherwise stated, plants are observed and the results recorded approximately 4 weeks after sowing and treatment. Tables I and II below summarize these results. Evaluation of herbicidal activity is obtained using a fixed scale based on the percentage damage to each plant species. The rating is defined as follows:

% extermination Scale up to 240 to 491 to 742 to 1003

Post-emergence tests are performed as follows:

The active ingredients are applied by spraying on two or three weeks samples of different plant species. A solution or wettable powder suspension containing a suitable dose of the active ingredient to obtain the desired effect and a surfactant is applied to the plants. The treated plants are placed in a greenhouse and, unless otherwise stated, the effects of partial to complete inhibition are observed and recorded after approximately 4 weeks. The results are shown in Table I, in which the index of post-emergence herbal efficacy is as follows:

% Damage Scale up to 240 to 491 to 742 to 993

1004

The plant species used in these tests are identified by the letter according to the following key:

A - hairy soya В - sugar beet C - wheat

D - rice

E - Article

F - Beet

I - cannabis

J - White Goosefoot

К - crest L - cloud

M - roof brome N - millet

G - wild buckwheat O - hedgehog corns H - barley P - dew

Table 1

Preemergence plant species

nina , WAT ⁺ kg / ha AND В C D E F G H AND J К L M N O P 3 4 1.12 2 2 1 3 2 1 2 2 3 1 3 1 1 2 3 2 4 5.60 3 3 2 3 3 2 3 3 3 2 3 ’2 2. 3 3 2 4 4 1.12 3 2 0 3 1 0 2 1 3 2 2 1 2 2 3 2 4 5.80 3 2 1 3 3 1 3 2 2 3 3 2 2 3 2 3 6 4 1.12 1 2 1 2 2 0 2 2 2 2 3 1 2 2 3 3 4 5.60 2 3 2 3 2 2 3 2 2 2 2 2 2 2 3 3 7 2 1.12 1 1 0 1 0 0 0 1 1 1 0 0 0 0 0 1 4 5.60 2 2 1 2 2 1 0 1 2 2 1 1 0 0 2 2 8 4 1.12 1 2 1 1 1 0 1 2 2 2 2 1 2 0 2 2 4 5.60 2 2 2 3 2 1 2 2 3 2 3 1 2 1 3 3

⁺ weeks after treatment

Compound Table! WAT + kg / ha ABC D Post-emergence plant species N O P E F G H I J K L M 3 2 1.12 10 1 0 0 111 11110 0 0 0 4 5.60 110 0 0 111 0 1110 0 0 0 ⁺ weeks after treatment

These compounds were also tested according to the above procedure using the following plant species:

A - thistle sowing G - litter

B - beet H - creeping wheatgrass

I - Halle sorghum

J - brome

K - hedgehog corns the foot

C - cloud Ď - reindeer E - goosefoot F - crescent

The results are summarized in Table II.

Table II

Preemergence plant species With torches-

nina WAT + kg / ha AND (B) C D E F G H AND J TO 3 4 11.2 3 2 2 3 3 3 2 3 3 2 3 4 4 11.2 3 3 3 2 2 3 1 3 0 3 3 6 4 11.2 2 1 2 2 3 3 2 2 3 3 3 7 4 11.2. 3 0 2 1 1 2 0 1 0, 0 2 8 4 11.2 3 1 2 2 3 3 1 3 1 2 2

+ weeks after treatment

Table II

Post-emergence plant species

Compound WAT + kg / ha AND (B) C D E F G H AND J TO 3 4 11.2 2 2 2 2 4 4 0 3 2 2 3 4 4 11.2 1 1 1 1 2 2 1 0 1 2 2 6 4 11.2 1 1 1 1 1 1 1 1 1 1 1 7 4 11.2 0 1 1 1 1 1 0. 0 0 0 1 8 4 11.2 2 2 1 1 2 2 2 1 1 1 2

+ weeks after treatment

The above table shows one aspect of the present invention. It is the use of the compounds of the invention to kill or damage unwanted plants, i.e. weeds. However, a further aspect of the invention is the use of said compounds for controlling the growth of desired plants, especially dicotyledons such as legumes, trees and sugar beet.

Here, the "plant growth and development" regulation refers to the modification of the normal gradual development of the treated desired plant until agricultural maturity. Modifications such as the size, shape, color or structure of the treated plant or any of its parts are most commonly observed. Similarly, visual changes reveal changes in the amount of fruit or flowers. The above changes can be characterized as acceleration or delay of plant growth, leaf or canopy changes, increased branching, end inhibition, increased flowering, leaf fall, more intense root growth, increased cold hardness, etc. While many of these modifications are desirable, the most common is their effect on the economic result, which is the most important. For example, reducing plant growth allows more plants to grow per unit area. Darkening of the leaf color may indicate a higher efficacy of chlorophyll, ie a higher rate of photosynthesis.

Although the regulation of plant growth by the method of the invention may involve partial inhibition of plant growth, it does not involve complete inhibition or killing of such plants. The invention contemplates the use of such an amount of active ingredient that will modify the normal gradual development of the treated plant until agricultural maturity. Such amount of plant growth control may vary not only according to the material selected, but also according to the desired modifying effect, the plant species and their degree, development, plant growth environment and whether we intend a permanent or ephemeral effect. It is, however, appropriate for those skilled in the art to determine the desired amount of active ingredient.

Modification of plants can be accomplished by applying the active ingredient to the seeds, emerging seedlings, roots, stems, leaves, flowers, fruits or other parts of the plants. Such application can be carried out directly to the plant part or indirectly by application to the environment in which the plant develops.

When using isoxazole as an active ingredient in plant growth regulating agents, these compounds have been shown to be effective in controlling plant growth when tested. according to the following procedure.

Soybeans, Clark 63, grow in a greenhouse or growth chamber to a half-developed state. At this time, the plants are treated by immersion in

1973.21 aqueous solution of chemical, acetone and surfactant. The plants are grown for approximately two weeks under cold conditions (11-14 ° C) and then transferred to a greenhouse and grown at 24 ° C. Approximately four weeks after treatment, the plants are observed and compared with reference plants that have been immersed in water containing only surfactant. The results are summarized in Table III.

Table III

Concentration

Compound (ppm)

3133

400. 4266

6133 ¹ 7133 '

8133

Compound 3 was further tested as described below.

Several soybean plants, a variety of Williams, grew out of seeds in a greenhouse in plastic pots for one week, and at this time they were united per plant in each pot. When the second triple leaf (3 weeks) was fully developed, the plants were treated with a solution of the active ingredient in acetone and water. Aqueous Tween 20 was used as a surfactant.

When the fifth trifoliate leaf (4-5 weeks) to fully develop, cšetřené .... plants was compared with untreated plants and post referentními '~ ^u

Changes

Reduction of growth, development of sessile buds

Reduction of growth, development of sessile buds

Reduction of growth, development of sessile buds dark color of leaves, inhibition of peak development

Reduction of growth, development of sessile buds inhibition of leaves

Reduction of growth, development of sessile buds, curvature of stem, curvature of leaves, inhibition of leaves, inhibition of peak development

Reduction in stature, epinastic stature, stimulation of sessile bud development, inhibition of the leaves of visualization are noted. At doses of 2.8, 0.56 and 0.112 kg / ha, growth reduction, foliage change, rosette growth, altered canopy and inhibition of plant peak development are observed.

Compound 3 was also tested on various tree species. The seedlings of these trees are placed in pots and placed in a greenhouse after being grown in a low temperature (4 ° C) environment for approximately two months. When buds develop and new growth occurs, the stem and leaves are treated with an aqueous solution of compound 3, acetone, cyclohexanone and an emulsifier. Table IV summarizes the observations.

Table IV

Kind of tree

Dose mg / plant

Observation time (days) after treatment Changes

Trnovník 50 7 to 29 Red oak 20 May 28 Sykomora americká 8 70 Sykomora americká 4 70 2 70

Reduction of growth, epinastic growth of leaves, inhibition of leaves, inhibition of branch growth

Reduction of growth, epinastic growth of leaves, stimulation of sessile buds, inhibition of leaves, inhibition of peak development

Reduction of growth, epinastic growth of leaves, stimulation of sessile buds, change of leaves, inhibition of leaves, inhibition of peak development, inhibition of branch growth, enlarged nodes, larger number of branches at nodes

Reduction of growth, epinastic growth of leaves, stimulation of sessile buds, change of leaves, inhibition of leaves, inhibition of peak development, inhibition of branch growth, enlarged nodes, larger number of branches at nodes

Reduction of growth, epinastic growth of leaves, stimulation of sessile buds, change of leaves, inhibition of leaves, inhibition of peak development, inhibition of branch growth, enlarged nodes, larger number of branches at nodes

Compound 3 is used in the form of an aqueous solution of acetone, cyclohexanone and an emulsifier. The 5 to 7 leaf stage sugar beet plants are treated with this solution by sprinkling the leaves. Table V summarizes the results of the observations made 28 to 126 days after treatment.

Table V

Dose (ppm) Changes

Reduction of growth, inhibition of leaves, development of sessile buds

100 Growth reduction, leaf inhibition, reduced beet size, sessile bud development

The compounds of the invention are effective in regulating the growth of various monocotyledons as well as dicotyledons. Compound 3 was tested on various grasses as described below. A mixture of Creeping Red Fescue and Chewings Fescue is planted in top-quality topsoil in plastic pots. Seven to ten days after germination, the plants are treated with the active ingredient to which a surfactant is added by spraying the plants until they are wetted to various concentrations. The results are summarized in Table VI.

Table VI

Height (1% control) at -

Dose (ppm) weeks after treatment weeks after treatment

10293

9486

250 6657

Compound 3 is applied to a four-week bell (Bluetoell Rice) at a dose of 250 ppm. By comparison with the standard, reduction in growth and expulsion of the offspring is observed at 3 weeks and at 7 weeks after treatment.

Compound 3 is also applied to four-week sorghum (Grain Sorghum) at a dose of 250 ppm. The results are summarized in Table VII.

Table Vil

Weeks after treatment

Plant height (° / o regulation)

Other changes

Chlorosa, necrosis Nekroso

Table VIII below summarizes the observations made when Compound 3 is applied to barley (Larber Barley).

Table VIII Time after treatment Observation time (weeks after treatment) Concentration (ppm) Plant height (0 / o regulation) 16 days 3 250 90 16 days 6 250 97 42 days 3 10 93 42 days 3 50 106 42 days 3 250 90

Table IX summarizes the observations when compound 3 is applied to Cheyenne wheat.

197321 17 18 Table IX Time of observation Concentration Plant height Time after treatment (weeks after treatment) (PPm) (° / o regulation) 15 days 3 250 80 15 days 6 250 9Í 42 days 3 10 113 42 days 3 50 112 42 days 3 250 109

The above data show that the compounds of the invention can be used as a herbicide or plant growth regulator for controlling monocotyledonous or dicotyledonous plants. When used as a herbicide, it is desirable to use rates above 2.24 kg / ha. When used as the growth regulator of the desired plants, dosages of less than 5.6 kg / ha, preferably 0.056 to 3.36, are preferably applied.

In selecting the appropriate application time and dosage of the active ingredient, it is to be understood that the exact dosage values also depend on the desired plant response, mode of use, plant variety, soil conditions and various other factors well known to those skilled in the art. While rates of 0.056 to 5.6 kg / ha are preferably used, higher rates of up to 56 kg / ha may be used depending on the above factors. It is also to be understood that single or multiple administration may be used to achieve the desired response.

In the practice of the invention, the active ingredient may be used alone or in combination with other pesticides or with the material referred to in the literature as an additive in either liquid or solid form. In order to prepare such a mixture, the active ingredient is admixed with an additive comprising solvents, fillers, carriers and activating agents to obtain mixtures in the form of finely divided solids, granules, pellets, wettable powders, dusts, solutions and aqueous dispersions or emulsions. Thus, the active ingredient can be used with an additive such as a finely divided solid, a liquid solvent of organic origin, water, a wetting agent, a dispersing agent or an emulsifying agent, or any suitable combination thereof.

Illustrative finely divided solid carriers and fillers to be used in the plant growth regulating compositions of the invention include talc, clays, pumice, quartz, fusori earth, silica, fuller's earth, sulfur, cork powder, ground wood, nutmeal, chalk, tobacco dust, charcoal and the like. Typical liquid solvents include Stoddard's solvent, acetone, alcohols, glycols, ethyl acetate, benzene, and the like. The growth regulators of the invention, particularly liquids and wettable powders, usually contain one or more surfactants in amounts sufficient to to make the composition readily dispersible in water or oil. The term "surfactant" refers to wetting agents, dispersing agents, suspending agents, and emulsifying agents. Such surfactants are well known and are described in U.S. Pat. No. 2,547,724, column. 3 and 4.

The active ingredients are generally administered in the form of a mixture comprising one or more ingredients which promote uniform distribution of the active ingredient in use. The application of liquid and particularly solid mixtures of the active ingredient can be carried out by conventional methods using, for example, sprayers, machine and hand powder sprayers and sprayers. Mixtures can also be applied from aircraft as dust or spray.

The compositions of the invention generally comprise from 1 to 99 parts of active ingredient, 1 to 50 parts of surfactant and 4 to 94 parts of solvent, all parts being by weight based on the total weight of the composition.

Although the present invention is described with respect to specific modifications, its details are not intended to be limiting, as it is understood that various equivalents, changes and modifications may be selected without departing from the spirit and scope of the invention, and it is understood that such equivalent embodiments are included within the scope of the invention.

I will invent the subject

Claims (3)

I will invent the subject A composition for controlling plant growth, characterized in that it contains from 1 to 99 parts by weight of a compound of the formula as active ingredient А-С — СЫ «2, о pyridyl rt & bo | ll N CB O 'ICF ₃ '. _n (CO 2) _n n is 0 or 1 and R represents a hydrogen atom, a C 1 -C 5 alkyl group or an agriculturally acceptable cation, provided that V can only represent pyridyl when n is 0. 2. A composition according to claim 1, wherein the active ingredient is methyl 2- [3- [3- (trifluoromethyl) phenyl] -5-isoxazolyl] benzoate. 3. A plant growth regulating agent according to claim 1, wherein the active ingredient is a compound of formula I wherein V is trifluoromethylphenyl. Severografla, n. P., Plant 7, Most