JPS5819672B2 - N-(2-propynyl)-carbanylic acid-(3-methoxycarbonylaminophenyl)-ester, process for producing the same, and selective herbicide containing the compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel N-(2-propynyl)-carba=)4
-(3-Methoxycarbonylaminophenyl)-ester, a process for the preparation of this compound, and selective herbicides containing this compound.

The herbicidal action of carbanilic acid (3-alkoxycarbonylaminophenyl) esters or diurethanes is already known (German Patent No. 1,567,115).

However, this compound is found in cruciferous plants (Beta-R
iiben).

Therefore, this compound has a large working gap.

The object of the invention is, inter alia, to provide herbicides which are completely compatible with important agricultural crops and which also have a herbicidal action against difficult-to-control weeds.

According to the present invention, this problem can be solved as an active ingredient using the general formula: [wherein R is a C,-C4-alkyl group,
- represents a propenyl group or 2-propynyl group, and X represents an oxygen atom or a sulfur atom]
The problem is solved by a herbicide characterized by containing -(2-propynyl)-rubanic acid-(3-methoxycarbonylaminophenyl)-ester.

The compounds according to the invention surprisingly exhibit a greater selective herbicidal action than known structurally analogous compounds with the same direction of action.

Another industrially important advantage of the compounds according to the invention is that, as new herbicides, they are effective against resistant weeds and exotic plants that are no longer adequately controlled by the herbicides known in practice due to the development of weed resistance. It can be used against people, so it depends on its actual use.

The compounds according to the invention are distinguished by a broad defoliating action.

This compound can be used for the control of dicotyledonous weeds.

In the case of this compound, foliage treatment can be used to eliminate field weeds, such as tellaria media, and foliage.
Matricaria chamomi l la)
, Lamium amplexicaul
e), Centaurea cya
nus), Obiyu (Amarantusretof)
1exus), Warunasubi (Solanumsac)
charoides), Eschol
tzia californica), round asagao (Ipomea purpurea), millet (Seta)
ria 1 talica) and other weeds.

For controlling seed weeds, consumption rates of 1 to 5 kg/ha of active substance are usually used.

In this case, the active substances according to the invention surprisingly demonstrated selectivity in useful agricultural crops, such as cotton, potatoes, corn, wheat and rice.

The compounds according to the invention can be used alone or in mixtures with one another or with other active substances.

Optionally, other plant protection agents or pest control agents can be added depending on the desired purpose.

Other herbicides can also be added, as long as it is intended to extend the range of action.

For example, herbicidal mixed ingredients include triazines, aminotriazoles, anilides, diazines, uracils, aliphatic and aryloxycarboxylic acids, hydrazides, amides, nitriles, esters of such carboxylic acids, carbamic acid esters and Agents from the group consisting of thiocarbamate esters, urea, 2,3,6-trichlorobenzyloxyisopropanol and hyrodane-containing agents are suitable.

Other additives are, for example, non-phytotoxic additives which produce a synergistic increase in herbicides, such as wetting agents, emulsifiers, solvents and oily additives.

The active substances or mixtures thereof according to the invention are preferably prepared with the addition of liquid and/or solid carriers or diluents and optionally wetting agents, adhesives, emulsifiers and/or dispersing agents.
It is used in dosage forms such as powders, dusting powders, granules, solutions, emulsions or dispersions.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons such as penzole, doluol, quidyol, cyclohexanone, isophorone, dimethyl sulfoxide, dimethyl formamide, and also mineral oil fractions.

Suitable solid carriers are minerals, such as tonesil, silica gel, talc, kaolin, attaclay, coalstone, silicic acid, and vegetable products, such as flour.

Examples of surfactants include calcium lignin sulfonate, polyoxyethylene-alkylphenol ether,
Mention may be made of naphthalene sulfonic acid and its salts, phenolsulfonic acid and its salts, formaldehyde condensation products, fatty alcohol sulfuric esters and substituted penzole sulfonic acids and its salts.

The content of active substance in the various preparations can vary within wide limits.

For example, the herbicides contain about 5-95% by weight of active substance, about 95-5% by weight of liquid or solid carrier and optionally up to 20% by weight of surfactant.

The pest control agent is sprayed in a conventional manner, for example, using water as a carrier at a spray rate of about 50 to 100 OA/ha.

The use of herbicides in the so-called micro- and ultra-trace methods is possible as well as their application in the form of so-called microgranules.

Among the compounds according to the invention, in particular R
is a methyl group, an ethyl group, an isopropyl group, an allyl group, a propynyl group, an isobutyl group, a See-butyl group, and X is an oxygen atom or a sulfur atom, especially R is an ethyl group, and X is an oxygen atom Compounds exhibiting this are superior due to their outstanding selective herbicidal action.

The novel compound according to the present invention is, for example, (a) a compound represented by the general formula: [R and X represent the above], N-(2-propynyl)-aniline represented by the formula: The reaction product is isolated in the usual manner, e.g. with the addition of an excess of amine or an inorganic base, e.g. caustic soda solution, sodium carbonate, potassium carbonate, a tertiary organic base, e.g. triethylamine. It can be manufactured by

Next, the production of the compounds of the present invention will be explained in detail with reference to Examples.

Example I N-(2-7" lopynyl)-carbanylic acid-(3-methoxycarbonylaminophenyl)-ester 39.4 f (0.3 mol) of N-(2-7" lopynyl)-aniline in 75 ml of acetic acid ethyl ester ) of 68.7 g (0.3 mol) of chlor M-(3-methoxycarbonylaminophenyl)-ester in 150 ml of ethyl acetate and at the same time water Potassium carbonate in 150ml 41.4
9 (0.3 mol) is added dropwise.

After stirring for 30 minutes at 10° C., the organic phase is then separated and washed with dilute hydrochloric acid and water with the addition of ice.

After drying with magnesium sulfate, evaporate and concentrate under reduced pressure.
Add 500 ml of isopropyl ether and then crystallize the reaction product.

Yield: 67.9 gou 69.8% of theoretical value Melting point: 104℃ Similarly, the following compounds according to the present invention can be produced.

The compounds according to the invention are soluble in inphorone, cyclohexanone, acetone, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide and other solvents;
Slightly soluble in water, penzol, toluene, etc.

The following examples serve to illustrate the applicability of the compounds of the invention in the form of their preparations.

Example 2 In a greenhouse, the compound of the present invention listed in the table was prepared as an aqueous emulsion or suspension, and 500 kg of water was mixed with 5 kg/h of the medium-active substance.
After 3 weeks of 6 treatments in which the plants were sprayed with a foliar treatment at a dosage of A, the treatment results were examined according to criteria 0, ■, 2.3.4, where 0 - represents no effect and 4 - extinction of the plants.

The results indicate that extinction of normal plants has been achieved.

Example 3 After germination of the plants listed in the table in a greenhouse, 1 k of the active substance as an aqueous emulsion is prepared with the compounds according to the invention and the known compounds.
The plants were treated by uniformly spraying the preparation at a usage rate of /ha.

After 3 weeks of treatment, the treatment results were examined according to the criteria 0 to 1o, where 0 represents total destruction and 10 represents no damage.

Although the compounds according to the invention exhibit excellent selective herbicidal action,
Known compounds are not shown.

Claims (1)

[Claims] 1 General formula: [In the formula, R is a C1-C4-alkyl group, ■-methyl-2
- a propenyl group or a 2-propynyl group, and X represents an oxygen atom or a sulfur atom]. 2. The compound according to claim 1, wherein R represents a methyl group, ethyl group, isopropyl group, allyl group, propynyl group, isobutyl group, see-butyl group, and X represents an oxygen atom or a sulfur atom. 3N-(2-propynyl)-rubanic acid-(3-methoxycarbonylamino-phenyl)-ester,
A compound according to claim 1. 4N-(2-7'lopinyl)-rubanilic acid-(3-(
2. A compound according to claim 1, which is methylthio-carbonylamino)-phenyl sea ester. 5N-(2-7”ropinyl>-carbanylic acid-(3-
The compound according to claim 1, which is (ethylthio-carbonylamino)-phenyl sea ester. 5N-(2-7”ropinyl)-carbanylic acid-(3-(
A compound according to claim 1 which is 2-propynyloxycarbonylamino)-phenyl sea ester. 7N-(2-7”ropinyl)-carbanylic acid-(3-(
A compound according to claim 1 which is 2-methylpropoxycarbonylamino)-phenylcouester. 8 N-(2-propynyl)-rubanic acid-(3-ethoxycarbonylaminophenyl)-ester,
A compound according to claim 1. 9N-(2-propynyl)-carbanylic acid-(3-(1
-Methylethoxycarbonylamino)-phenylcou ester. 1ON-(2-7”ropinyl)-rubanilic acid-(3-
Claim 1, which is (1-'f-2-propenyloxycarbonylamino)-phenylcouester
Compounds described in Section. 11 General formula: [In the formula, R is a C1-C4-alkyl group, ■-methyl=2
-propenyl group or 2-propynyl group, X represents an oxygen atom or a sulfur atom];
--y''ropinyl)-carbanylic acid-(3-methoxycarbonylaminophenyl)-ester, a compound represented by the general formula: [wherein R and X represent the above] is prepared by the formula: N-(2-propynyl)-aniline, characterized in that it is reacted with N-(2-propynyl)-aniline represented by the formula in the presence of an acid binder, and the reaction product is isolated by a conventional method. A method for producing acid-(3-methoxycarbonylaminophenyl)-ester. 12 N-(2-propynyl) represented by the general formula: [wherein R represents an ethyl group and X represents an oxygen atom] as an active ingredient. ) - Rubanilic acid -
A selective herbicide characterized by containing one or more (3-methoxycarbonylaminophenyl)-esters. 13. The selective herbicide according to claim 13, which is mixed with a carrier and/or an auxiliary agent.