CS209949B2 - Herbicide means and method of making the active substance - Google Patents

Abstract

Novel compounds of the general formula I <IMAGE> (wherein R represents C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl and X represents O or S) and their manufacture. The compounds have a herbicidal action, especially a selective herbicidal action, and accordingly may be made up with suitable carriers into herbicidal preparations and may be used for protecting living plants and crop areas against weeds.

Description

(54) Herbicidal composition and method of manufacture of an active ingredient

2

A herbicidal composition and a process for the manufacture of an active ingredient. The present invention is in the field of herbicidal compositions. The herbicidal composition according to the invention contains, as active ingredient, one or more of the 3-methoxycarbonylaminophenyl esters of N- (2-propynyl) -carbaniilic acid of the formula I

CH, -C =CH

O-CO-H

NH-C-X-R

II ⁰ (!)

in 'which represents RC _{(-C 4} alkyl, C ₃ -C ₄ alkenyl, C ₃ -C not aíkinyl а X ₄ is oxygen or sulfur,

The invention relates to herbicidal compositions which contain one or more 3-methoxycarbonylaminophenyl N- (2-propynyl) carbanilic acid esters as an active ingredient and a process for the preparation of these novel compounds.

The herbicidal effect of carbanilic acid 3-alkoxycarbonylamino-phenyl esters or diurethanes is already known (DE Patent 1 567 115).

However, these compounds have sufficient selectivity only in beet. Furthermore, these compounds exhibit large gaps in action.

SUMMARY OF THE INVENTION It is an object of the present invention to provide a weed control composition which also has an effect against hard-to-control weeds, in particular at full tolerance for important agricultural crops.

This object is achieved according to the invention by a composition which is characterized by the content of one or more of the 3-methoxycarbonylaminophenyl esters of N- (2-propynyl) carbanilic acid of the general formula I

CH 2 Cl 2 / z

nh-c-x-r

II ⁰ (I) in which

R is Ci-C ₄ alkyl, C ₃ -C ₄ -alkenyl or C ₃ -C ₄ alkynyl,

X is oxygen or sulfur.

Surprisingly, the compounds of the invention have a greater selective herbicidal activity than known, constitutionally analogous compounds of the same direction of activity.

Another technically important advantage of the compounds according to the invention lies in their practical application in that they can be used as novel herbicides against resistant weeds and secondary flora which can no longer be sufficiently controlled by the known herbicides due to the emergence of weed resistance.

The compounds of the invention are characterized by a broad foliar herbicidal action. They can be used to control dicotyl weeds. The compounds according to the invention after the emergence of the weed control field weeds such as chickweed (Stehlaria media), camomile (Matricaria chamomilla), dead-nettle (Lamium aimplexicaule), Centaurea cyanus, amaranth (Amlaranthus retroflexus), solar saccharoides, Eschholtzia cnica purpurea), Italian grassland (Setaria itajlica.) and other weeds.

Usually, at least 1 kg to 5 kg of active ingredient / ha is used for weed control. Surprisingly, the compounds according to the invention show selectivity in crops of useful plants, such as cotton, potatoes, corn, wheat and rice.

The compounds of the invention may be used either alone, in admixture with each other or in admixture with other active ingredients. If desired, other plant protection or pest control agents may be added, depending on the desired purpose.

Other herbicides may also be added to broaden the spectrum of activity. Suitable herbicidally active partners are, for example, active compounds from the groups of triazines, aminotriazoils, anilides, diazines, uracils, aliphatic carboxylic acids and aryloxycarboxylic acids, hydrazides, amides, nitriles, esters of these carboxylic acids, esters of carbamic and thiocarbamic acids 2,3,6-trichlorobenzyloxyxopropanol, rhodane-containing compositions and others. Like · other ingredients are; for example, it also encompasses non-phytotoxic additives which increase the synergistic effect of the herbicides, e.g. wetting agents, emulsifying agents, solvents and oily additives.

Suitably, the active compounds according to the invention or mixtures thereof are used in the form of preparations such as powders, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and optionally wetting agents, emulsifiers and / or auxiliary dispersing agents.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethylsulfoxide, dimethylformamide, and mineral oil fractions. ¹

As; The solidified carriers are suitable for mineral soils such as tonsil, silica gel, talc, kaolin, attaclay, limestone, silicic acid and plant products such as flour.

Examples of surfactants which may be mentioned are calcium lignin sulphonate, polycetylene alkylphenol ether, naphthalenesulphonic acids and their salts, phenol sulphonic acids and their salts, formaldehyde condensates, fatty alcohol sulphates, and substituted benzenesulphonic acids and their salts.

The proportion of active compound (s) in the various preparations can vary within wide limits. For example, the compositions contain about 5 to 95 weight percent of the active ingredient, about 95 to 5 weight percent of liquid or solid carriers, and optionally up to 20 weight percent of surfactants.

The dispersion of the compositions can be carried out in a conventional manner, for example with water as carrier ¹ in a spray slurry amount of about 50 to 1000 liters / ha. It is also possible to use the compositions by the so-called small-volume and ultra-small-volume processes, or it is possible to apply them in the form of so-called microgranules.

The compounds according to the invention exemplify209949 for their selective herbicidal activity, in particular those in which, in the aforementioned general formula, R is methyl, ethyl, isopropyl, allyl, propynyl, isiobutyl, sec.butyl, sec.butenyl or sec.butinyl and X oxygen or sulfur.

The naïve compounds of the invention may be prepared, for example, by reacting compounds of general formula I in the presence of an acid acceptor, for example with the addition of excess amine, or an inorganic base such as sodium hydroxide, sodium carbonate, potassium carbonate or a tertiary organic base such as triethylamine. II in the presence of a tertiary organic base, such as, for example, triethylamine or ¹ pyridine, or alkali metal salts, are reacted with N-phenyl-N- (2-prop The compound is of formula (V)

CH © C- CH &

Coη-what-a

(IN)

o-coct nh-c-x-r

II ⁰ (ID with N- (2-propynyl) aniline of the formula III

H ~ N

CH; C = CH

(WD

The novel compounds can also be prepared, for example, by reacting compounds of formula IV

OH

NH-C-X-R (IV) wherein R and X are as previously defined.

Priority shall be given to the manufacturing method 'first'.

The following example illustrates the preparation of the compounds of the invention.

Example 1 N- (2-propynyl) carbonic acid

A solution of 68.7 g (0.3 mol) was added dropwise to a solution of 39.4 g (0.3 mol) of N- (2-propynyl) aniline in 75 ml of ethyl acetate with stirring and cooling to 8 ° to 12 ° C. 3-methoxycarbonylamino-phenyl chloroformate in 150 ml of ethyl acetate and a solution

41.4 g (0.3 mol) of potassium carbonate in 150 ml of water are stirred for 30 minutes at 10 DEG C., the organic base is then separated off and washed with dilute hydrochloric acid and water under the addition of ice. It is evaporated under reduced pressure and 500 ml of isopropyl ether is added, whereupon the reaction product crystallizes.

Yield: 67.9 g = 69.8% of theory.

The following compounds of the invention were prepared in an analogous manner.

Name of the compound

Physical constants

N- (2-propynyl) carbanilic acid 3- (methylthiocarbonylphenyl) aminophenyl ester

3- (Ethylthioicarbonylamino) phenyl N- (2-propynyl) carbanilic acid ester

3- (2-Propyne ШххкагЬопу 1йгп ino) phenyl ester of N- (2-proipinyl) carbanilic acid

N- (2-propynyl) carbanilic acid 3- (2-methylpnopoxycarbonylamino) phenyl N- (2-propynyl) carbamyl 3-ethynylcarbonyl ester

3- (НМеОзу Mh oxycarbonylamino) phenyl N- (2-propynyl) carbanilic acid N- (2-propynyl) carbanilic acid phenyl ester

mp: 130 ° C

mp: 99 ° C

mp: 118 ° C

mp: 108 ° C

mp: 101-103 ° C

mp: 78-79 ° C

mp: 96-97 ° C

The compounds of the present invention are soluble in isophorone, cyclohexanone, acetone, tetrahydrofuran, dimethylformamide, dimethylsulfonyl oxide and other solvents, and are sparingly soluble in water, benzene, toluene and the like.

The following examples serve to explain the possible uses of the compounds of the invention in the form of their preparations.

Example 2

The compound of the invention was listed in the greenhouse

N- (2-propynyl) carbanilic acid 3- (methylthiocarboinylamino) phenyl ester

N- (2-propynyl) carbanilic acid 3- (ethylthiocarbohylaminophenyl ester)

3- (2-Propynyloxycarbonylamino) phenyl N- (2-propynyl) carbanilic acid ester

3- (2-Methylprop'Oxykarbonylamino) phenyl N- ^(2-ргор, 1пу1) carbanilic

3-Ethoxycarbinylaminophenyl ester

N- (2-propynyl) carbanil

3- [1-Methoxy-ethoxy-methyl-phenylamino] -phenyl ester of N- (2-propynyl) carbanilic acid

3- (1-Methyl-2-propenyloxy-carbonylamino) phthalic acid N- (2-propynyl) carbrnil

Untreated products according to the invention as aqueous emulsions or as suspensions in an amount of 5 kg of active ingredient / ha in 500 liters of water per ha sprayed onto the plants after emergence.

Three weeks after treatment, the treatment results were evaluated, and according to Scheme 0, 1, 2, 3, 4 = = no effect = plant destruction

The result shows that plant destruction has generally been achieved.

Sola.num Brassica 4 4 4 4 4 4 4 4 4 4 4 4 4 4 0 0

= no effect = destruction of plants

Example 3

In the greenhouse, the plants listed in the table were treated after emergence with the compound of the invention and the known compound in the form of an emulsion in an amount of 1 kg of active substance / ha by uniformly spraying the preparations over the plants.

Three weeks after treatment, the treatment results were evaluated according to Schemes 0-10, indicating

0 · = complete destruction = no damage

The compound of the invention showed an excellent selective herbicidal effect, but the known compound did not.

299949

Compound of the Invention Cotton Maize Stenaria Amaranthus Wheat ^: Clithy-allium sp. Senecio Setaria media retrofleuus iuu®getum vulgaris italica

Claims (2)

SUBJECT OF THE INVENTION A herbicidal composition, characterized in that it contains, as active ingredient, one or more 1-muthooycarbonylaminotenyl esters of N- (2-propynyl) carbanilic acid of the general formula: CH 2 Cl 2 / i O-CO-N (!) In which 3. A process for the preparation of 3-methoxycarbonylamino-phenyl esters of N- (2-propynyl) carbanilic acid as active ingredient according to claim 1, characterized in that the compounds of the general formula II are ⁰ (II) in which X and R are as defined in 1, in the presence of accepto.ru acids are reacted with N- [2-propynyl] aniline of formula III R is -C 1 -C 4 alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkenyl, X is oxygen or sulfur. 2. A composition according to claim 1, characterized in that as active substance · includes compounds of formula I wherein R ¹ represents methyl, ethyl, isopropyl, allyl, propynyl, iskbbutyl, sec-butyl, or sek.buteniyl sek.butinyl and X is oxygen or sulfur.