GB2040939A - Herbicidally active diurethanes and their manufacture and use - Google Patents
Herbicidally active diurethanes and their manufacture and use Download PDFInfo
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Abstract
Novel diurethanes of the general formula I <IMAGE> (wherein R1 represents C1-C4-alkyl or phenylethyl, R2 represents C1-C4- alkyl, halogeno-C1-C4-alkyl, C2-C4- alkenyl or -alkynyl or halogeno- C2-C4-alkenyl or -alkynyl, Y represents H or F and X represents O or S) have a 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
SPECIFICATION
Herbicidally active diurethanes and their manufacture and use
The present invention is concerned with new diurethanes, with processes for the manufacture of these compounds and with their use as herbicidal agents.
The herbicidal action of diurethanes is already known. Known active substances of this kind have a selective herbicidal action especially in beet crops (German Patent Specification No. 1.567,151) or in soya beans (German Patent Specification No. 2,638,897).
The problem upon which the present invention is based has been to develop a herbicidal agent which has a very good action against weeds that are difficult to control and, at the same time, exhibits a tolerance especially in cotton crops.
This problem is solved according to the present invention by the compounds of the general formula i, as defined below.
The present invention accordingly provides compounds of the general formula I
in which R1 represents a C1-C4-alkyl or phenylethyl group,
R2 represents a C1-C4-alkyl, halogeno-C1-C4-alkyl, C2C,4-alkenyl, halogeno-C2-C4-alkenyl, C2-C4-a Ikynyl or ha logeno-C2-C4-a Ikynyl group,
Y represents a hydrogen or fluorine atom and
X represents an oxygen or sulphur atom.
The compounds of the present invention, surprisingly, exhibit an outstanding tolerance in cotton crops which is not the case with known compounds of analogous constitution.
In addition, they have a very good action against weeds that are difficult to control, for example
Amaranthus, Stellaria, Matricaria and others, which can be controlled by both the pre-emergence and the post-emergence methods.
Application quantities within the range of from 1 to a maximum of 5 kg of active substance per hectare are generally sufficient to control these seed weeds, the compounds of the present invention exhibiting a selective action also in useful plant crops other than cotton, for example soya, ground-nut, potatoes, maize, rice, sorghum and cereals. When two or more compounds of the present invention are used, the range of 1 to 5 kg refers of course to the total application quantities of these compounds.
The present invention accordingly also provides a herbicidal preparation which comprises a compound of the general formula I, in admixture or conjunction with a suitable carrier. The preparation may of course contain one or more compounds of the general formula I.
The present invention further provides a method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is'treated with a compound of the general formula
The present invention further provides a method of protecting a crop area against weeds, wherein the crop area is treated with a compound of the general formula I.
The present invention further provides a pack which comprises a compound of the general formula i together with instructions for its use as a herbicide.
The compounds of the present invention may be used either singly or in the form of mixtures with one another or with other active substances. If desired, other piant-protecting agents and/or pesticides may be added, depending on the desired aim.
If a broadening of the range of action is intended, other herbicides may also be added. As suitable herbicidally active co-components there may be mentioned, for example, active substances from the groups of triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carboxytic acids and halocarboxylic acids, substituted benzoic acids and aryloxycarboxylic acids, hydrazides, amides, nitrides, esters of such carboxylic acids, carbamic acid esters and thiocarbamic acid esters, ureas, 2,3,6trichlorobenzyloxyisopropanol and thiocyanogen-containing agents.
Furthermore, other additives may also be used, for example non-phytotoxic additives which with herbicides produce a synergistic increase in action, for example wetting agents, emulsifiers, solvents and oily additives.
The active compounds of the present invention or mixtures containing them are advantageously used in the form of herbicidal preparations, for example powders, strewable preparations, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid vehicles or diiuents and, if desired, of surface-active agents, for example wetting, adhesive, emulsifying and/or dispersing auxiliary agents.
Suitable liquid carriers are, for example, water, aliphatic hydrocarbons, aromatic hydrocarbons, for example benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide and dimethylformamide, and also mineral oil fractions.
Suitable solid carriers are, for example, mineral earths, for example tonsil, silica gel, talcum, kaolin, attaciay, limestone and silicic acid, and vegetable products, for example meals.
As surface-active agents there may be mentioned, for example, calcium lignin sulphonate, polyoxyethylenealkylphenol ethers, naphthale nesulphonic acids and salts thereof, phenolsuiphonic acids and salts thereof, formaldehyde condensates, fatty alcohol sulphates and also substituted benzenesulphonic acids and salts thereof.
The proportion of the active substance or substances in the various herbicidal preparations may vary within wide limits. For example, the preparations may contain approximately 5 to 95% by weight of active substance(s), approximately 95 to 5% by weight of liquid or solid carrier and also, if desired, up to 20% by weight of surface-active agent(s).
The active compounds may be applied in the usual manner, for example with water as the carrier in spray liquor quantities of approximately 50 to 1000 litres/hectare. It is also possible to apply the active compounds by the so-called low-volume andultra-low-volume methods as well as to apply them in the form of so-called microgranules.
As groups represented by the symbol R1 in the general formula I there may be mentioned, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl and 2-phenylethyl groups, and as groups represented by the symbol R2, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.
butyl, allyl, propargyl, chlorethyl, 1 -chloromethylethyl, 4-chlorobutynyl, 1 -methylpropynyl and 4chlorobutenyl groups.
Compounds of the present invention which are distinguished by an outstanding selective herbicidal action are especially N-ethyl-3-fiuorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester,
N-ethyl-3-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester, N-ethyl-3-fluorocarbanilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl] ester, N-ethyl-4-fluorocarbanilic acid (3-ethoxycarbonyl- aminophenyl) ester, 4-fluoro-N-methylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester, N-ethyl-3fluorocarbanilic acid [3-(1 -methylethoxycarbonylamino)-phenyl] ester, N-ethyl-4-fluorocarbanilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl] ester, 4-fluoro-N-methylca rba nilic acid [3-(1 1-methyl ethoxycarbonylamino)-phenyl] ester, 3-fluoro-N-methylcarbanilic acid [3-( 1 methylethoxycarbonyl- amino)-phenyl] ester, N-ethyl-3,4-difluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester and
N-ethyl-2-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester.
The new compounds of the general formula I may be manufactured, for example, by the process of the present invention, as defined below.
The present invention accordingly further provides a process for the manufacture of the compounds of the general formula I, wherein
a) a compound of the general formuta
in which R2 and X have the meanings given above, is reacted with an amine of the general formula
in which iR, and Y have the meanings given above, in the presence of an acid acceptor, for example with the addition of an excess of the amine or of an inorganic base, for example a sodium hydroxide solution, sodium -carbonate or potassium carbonate, or a tertiary organic base, for example triethylamine, or
b) a compound of the general formula
in which R2 and X have the meanings given above, is reacted in the presence of a tertiary organic base, for example triethylamine or pyridine, or is reacted in the form of an alkali salt thereof with a carbamoyl chloride of the general formula
in which R, and Y have the meanings given above, each reaction being carried out at a temperature within the range of from 0 to 1 000C, or
c) a nitro compound of the general formula
in which R1 and Y have the meanings given above, is catalytically hydrogenated, for example by using nickel in methanol, to form the corresponding amino compound which is then reacted with a compound of the general formula CI-C0-X-R2, in which R2 and X have the meanings given above, in the presence of an acid acceptor, for example an inorganic base, for example a sodium hydroxide solution, sodium carbonate or potassium carbonate, or a tertiary organic base, for example triethylamine.
The compounds of the general formula I formed by any one of the variants (a) to (c) may be
isolated in the usual manner.
The compounds of the present invention are soluble in acetone, cyclohexanone, isophorone, tetrahydrofuran, dimethylformamide, dimethyl sulphoxide and ethyl acetate.
The following Examples illustrate the invention. Example 1 illustrates the manufacture of the compounds of the present invention and Examples 2 to 4 illustrate the possible ways of using the compounds of the present invention and, in the case of Example 4, compares their herbicidal action with that of known compounds.
EXAMPLE 1
N-Ethyl-3-fluorocarbanilic acid J3-(ethylthiocarbonylamino)-phenyl] ester
To a solution of 13.9 g (0.1 mole) of N-ethyl-3-fluoroaniline in 70 ml of ethyl acetate there were added dropwise, while stirring and cooling to 10 to 1 50C, a solution of 26.0 g (0.1 mole) of chloroformic acid [3-(ethylthiocarbonylamino)-phenyl] ester in 70 ml of ethyl acetate and, at the same time, a solution of 13.8 g (0.1 mole) of potassium carbonate in 50 ml of water. Stirring was continued for 30 minutes at 1 50C, and the organic phase was then separated and, with the addition of ice, washed with dilute hydrochloric acid and water. After drying with magnesium sulphate, the mixture was concentrated by evaporation under reduced pressure. The residue after evaporation was recrystallized from ethyl acetate/pentane.
Yield: 29.4 g = 81% otthe theoretical yield of N-ethyi-[3-fluorocarbanilic acid 3 (ethylthiocarbonylamino)-phenyl] ester.
M.p.: 1270C.
The following compounds of the present invention may be manufactured in an analogous manner.
Name of the compound Physical Constant 3-Fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 105-107 C
N-Ethyl-3-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 108-109 C N-Ethyl-3-fluorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester M.p.: 125127 C 4-Fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 96-970C 4-Fluoro-N-methylcarbanilic acid [3-(methylthiocarbonylamino)phenyl] ester M.p.: 106-1 080C N-Ethyl-4-fluorocarbanilic acid [3-(methylthiocarbonylamino)phenyl] ester M.p.: 143-1 440C N-Ethyl-4-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 117-11 80C N-Ethyl-4-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester M.p.: 76-77 C
N-Ethyl-3-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester M.p.: 1 220C 3-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester M.p.: 91-92 C 3-Fluoro-N-methylcarbanilic acid [3-methylthiocarbonylamino)phenyl] ester M.p.: 116 C 3-Fluoro-N-methylcarbanilic acid [3-(ethylthiocarbonylamino)phenyl] ester M.p.: 124-125 C 4-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester n20: 1.5472 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonyla minophenyl) ester M.p.: 137 C 4-Fl uoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxycarbonyla minophenyl)
ester M.p.: 103-104 C
N-Ethyl-3-fluorocarbanilic acid [3-(l]methylethoxycarbonylamino)phenyl] ester M.p.: 98 C
N-Ethyl-4-fluoroca rba nilic acid [3-(1 -methylethoxycarbonylamino)-phenyl]
ester M.p.: 84-86 C 4-Fluoro-N-methylcarbanilic acid [3-(1-methylethoxycarbonylamino)phenyl]
ester M.p.: 88 C
N-Ethyl-4-fluorocarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester M.p.: 790C 4-Fluoro-N-methylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester M.p.: 97-99 C 3-Fl uoro-N-methylca rbanilic acid [3-(2-propynyloxycarbonyla mino)-phenyl] ester M.p.: 142-144 C
N-Ethyl-3-fluoroca rbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester M.p.: 148-150 C 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)- phenyl] ester M.p.: 117 C 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( 1 -methylethoxycarbonyl- amino)-phenyl] ester M.p.: 81-83 C
N-Ethyl-4-fluorocarbanilic acid (3-allyloxycarbonylaminophenyl) ester M.p.: 73-74 C
N-Ethyl-4-fluorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester M.p.: 79-80 C
Name of the compound Physical Constant 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyloxycarbonylaminophenyl)
ester M.p.:810C 3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylamino- phenyl) ester M.p.: 112-113 C
N-Ethyl-2-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 106-107 C
N-Ethyl-3,4-difluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester M.p.:121-1 220C 3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxycarbonylaminophenyl)
ester M.p.: 1150C 3-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamio)
phenyl] ester M.p.: 91-930C 3-Fluoro-N-methylca rba nilic acid [3-( 1 -methylethoxyca rbonyla m ino)
phenyl] ester M.p.: 74-760C 3-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester M.p.: 78-80 C 3-Fluoro-N-ethylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester M.p.: 101-103 0C 4-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester n20: 1.5536
N-Ethyl-3-fluorocarbanilic acid [3-(1-chloromethylethoxycarbonylamino)
phenyl] ester M.p.: 68-700C N-Ethyl-3,4-difluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester M.p.: 69-700C N-Ethyl-3 4-difluorocarbanilic acid [3-( methylthiocarbonylamino)-phenyl] ester M.p.: 130-1320C 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylamino
phenyl) ester M.p.: 125-126 C 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxycarbonylaminophenyl)
ester M.p.: 128-1300C 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(methylthiocarbonylamino)
phenyl] ester M.p.: 148-149 C 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( ethylthiocarbonylamino)
phenyl] ester M.p.: 1240C 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(1 -methylethoxycarbonyl- amino)-phenyl] ester M.p.: 109-1100C 3-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) ester $M.p.: 90-92 C 3-FI uoro-N-propylca rbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester M.p.: 103-1050C 3-Fluoro-N-propylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester $M.p.: 103-105 C
N-Ethyl-3-fluorocarba nilic aid [3-(1 -methyl-2-propenyloxycarbonylamino)-
phenyl] ester M.p.: 100-101 C N-Ethyl-2-fluorocarbanilic acid [3-( 1 -methyl-2-propenyloxycarbonylamino)-
phenyl] ester M.p.: 109-110 C
Name of the compound Physical Constant
N-Ethyl-4-fluorocarbanilic acid [3-(1-methyl-2-propenyloxycarbonylamino)
phenyl] ester M.p.: 73-740C N-Butyl-3-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 79-800C 3-Fluoro-N-methylcarbanilic acid [3-(2-methylpropoxycarbonylamino)
phenyl] ester M.p.: 94-950C 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(1 -methyl-2-propenyloxy
carbonylamino)-phenyl] ester n20: 1.5578 3-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( 1 -methyl-2-propenyloxy- carbonylamino)-phenyl] ester n20: 1.5632 3-FI uoro-N-methylca rbanilic acid [3-(1 -methyl-2-propenyloxycarbonyl
amino)-phenyl] ester n20: 1.5509 4-FI uoro-N-methylca rbanilic acid [3-( 1 -methyl-2-propenyloxycarbonyl
amino)-phenyl] ester n20: 1.5465
N-Butyl-4-fluorocarbanilic acid [3-(1-methyl-2-propenyloxycarbonylamino)
phenyl] ester nD20: 1.5298 4-Fluoro-N-methylcarbanilic acid [3-(2-methylpropoxycarbonylamino)
phenyl] ester nD20: 1.5313 4-Fluoro-N-propylcarbanilic acid [3-(1 -methyl-2-propenyloxycarbonyl-
amino)-phenyl] ester M.p.: 75-760C N-Ethyl-2-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester M.p.: 151-1 530C N-Ethyl-2-fluorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester M.p.: 160-162 C
N-Ethyl-2-fluorocarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester M.p.: 146-147 C
N-Ethyl-2-fluorocarbanilic acid [3-(1-methylethoxycarbonylamino)-phenyl]
ester . M.p.: 126-1270C N-Ethyl-2-fluorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester M.p.: 1500C
2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyloxycarbonylaminophenyl)
ester M.p.: 72-730C 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(2-methylpropoxycarbonyl
amino)-phenyl] ester M.p.: 57-580C 4-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) ester n20: 1.5345
4-Fluoro-N-propylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester M.p.: 64-660C N-Butyl-4-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester nD20: 1.5322
N-Butyl-4-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester n20: 1.5305
4-Fluoro-N-butylcarbanilic acid [3-( 1 -methylethoxycarbonyla mino)-phenyl]
ester M.p.: 81-830C 4-Fluoro-N-butylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester M.p.: 73-75 0C N-Butyl-4-fluorocarbanilic acid 3-(2-propynyloxycarbonylamino)-phenyl]
ester
Name of the compound Physical Constant 4-Fluoro-N-propylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester M.p.: 53-550C 4-Fluoro-N-propylcarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl] ester n20: 1.5461 N-Butyl-4-fluorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester M.p.: 85-890C 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(2-propynyloxycarbonyl
amino)-phenyl] ester M.p.: 93-940C EXAMPLE 2
In a series of tests carried out in a greenhouse, the compounds of the present invention listed in the Table below were each sprayed in accordance with the post-emergence method at a rate of application of 5 kg of active substance per hectare, emulsified in 500 litres of water per hectare, on to
Brassica and Solanum as the test plants. 3 weeks after the treatment the results thereof were evaluated and expressed by a numerical scale extending from 0 to 4, the value 0 representing no action and the value 4 representing destruction of the plant.
As will be seen from the Table, destruction of the plants was achieved.
Compound of the invention Solanum Brassica 3-Fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4
N-Ethyl-3-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 N-Ethyl-3-fluorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester 4 4 4-Fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 4-Fluoro-N-methylcarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester 4 4
N-Ethyl-4-fluorocarbanilic acid [3-( methylthiocarbonylamino)-phenyl] ester 4 4 N-Ethyl-4-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 N-Ethyl-4-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4 N-Ethyl-3-fluorocarbaniiic acid (3-ethoxycarbonylaminophenyl) ester 4 4 3-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4 3-Fluoro-N-methylcarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester 4 4 3-Fluoro-N-methylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester 4 4 4-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylaminophenyl)
ester 4 4 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxycarbonylaminophenyl)
ester 4 4
N-Ethyl-3-fluoroca rba nilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl]
ester 4 4 N-Ethyl-4-fluorocarbanilic acid [3-(1 -methylethoxycarbonylamino)-phenyl]
ester 4 4 4-Fluoro-N-methylcarbanilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl] ester 4 4
Compound of the invention Solanum Brassica
N-Ethyl-4-fluorocarbanilic acid i3-(ethylthiocarbonylamino)-phenyl] ester 4 4
4-Fluoro-N-methylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester 4 4
3-Fluoro-N-methylcarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester 4 4
N-Ethyl-3-fluorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl] ester 4 4 4-Fl uoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)-phenyl]
ester 4 4 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( 1 -methylethoxycarbonylamino)
phenyl] ester 4 4
N-Ethyl-4-fluorocarbanilic acid (3-allyloxycarbonylaminophenyl) ester 4 4
N-Ethyl4-fluorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl] ester 4 4 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyloxycarbonylaminophenyl) ester 4 4
3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylaminophenyl)
ester 4 4 3-Fluoro-N-methylca rbanilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl]
ester 4 4 3-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester 4 4 3-Fluoro-N-ethylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester 4 4 4-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester 4 4
N-Ethyl-3-fluorocarbanilic acid [3-(1 -chloromethylethoxycarbonylamino)- 4 4 phenyljester N-Ethyl-2-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 N-Ethyl-3,4difluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4
3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxycarbonylaminophenyl)
ester 4 4
3-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)phenyl]
ester 4 4
3-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)phenyl]
ester 4 4 N-Ethyl-3,4-difl uoroca rbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4 N-ethyl-3,4-difluorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester 4 4
2-Fluoro-N-(2-phenyiethyl)-carbanilic acid (3-methoxycarbonylaminophenyl)
ester 4 4 2-FI uoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxyea rbonyla minophenyl)
ester 4 4
2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( methylthiocarbonyla mino)
phenyl] ester 4 4
Compound of the invention Solanum Brassica 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)phenyl]
ester 4 4
2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( 1 -methylethoxycarbonylamino)
phenyl] ester 4 4 2-Fluoro-N-(2-phenylethyl-carbanilic acid [3-(2-propynyloxycarbonylamino)
phenyl] ester 4 4
N-ethyl-2-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4
N-ethyl-2-fluorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester 4 4
N-ethyl-2-fluorocarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester 4 4
N-Ethyl-2-fluorocarbanilic acid [3-(1-methylethoxycarbonylamino)-phenyl]
ester 4 4
N-Ethyl-2-fluorocarbanilic acid [3-(2-propynyloxyca rbonylamino)-phenyl] ester 4 4 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-a 11yloxyea rbonylaminophenyl) ester 4 4 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(2-methylpropoxycarbonyl amino)-phenyl ester 4 4 4-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 4-Fluoro-N-propylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4
N-Butyl-4-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4
N-Butyl-4-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4 4-Fluoro-N-butylca rbanilic acid [3-( 1 -methylethoxycarbonyla mino)-phenyl]
ester 4 4 4-Fluoro-N-butylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester 4 4 N-Butyl-4-fluorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl] ester, 4 4 4-Fluoro-N-propylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester 4 4 4-Fluoro-N-propylcarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester 4 4
N-Butyl-4-fluorocarbanilic acid [3-(methylthiocarbonylamino)-phenyi] ester 4 4
N-Ethyl-3-fluorocarbanilic acid [3-(1-methyl-2-propenyloxycarbonylamino)
phenyl] ester 4 4 N-ethyl-2-fluoroca rba nilic acid [3-( 1 -methyl-2-propenyloxycarbonylamino)-
phenyl] ester 4 4
N-ethyl-4-fluorocarbanilic acid [3-(1-methyl-2-propenyloxycarbonylamino)
phenyl] ester 4 4
N-Butyl-3-fluorocarbanilic acid (3-methoxywarbonylaminophenyl) ester 4 4 3-Fluoro-N-methylcarbanilic acid [3-(2-methylpropoxycarbonylamino)-phenyl]
ester 4 4 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( 1 -methyl-2-propenyloxy- carbonylamino)-phenyl] ester 4. 4
Compound of the invention Solanum Brassica 3-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( 1 -methyl-2-propenyloxy
carbonylamino)-phenyl] ester 4 4 3-Fluoro-N-methylcarbanilic acid [3-( 1 -methyl-2-propenyloxycarbonyla mino)
phenyl] ester 4 4 4-Fluoro-N-methylcarba nilic acid [3-( 1 -methyl-2-propenyloxycarbonyla mi no)- phenyl] ester 4 4 N-ButyI-4-fluorocarbanilic acid [3-( 1 -methyl-2-propenyloxycarbonylamino)- phenyl] ester 4 4 4-Fluoro-N-methylcarbanilic acid [3-(2-methylpropoxycarbonylamino)
phenyl] ester 4 4 3-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 3-Fluoro-N-propylcarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester 4 4 3-Fluoro-N-propylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4
EXAMPLE 3
In a series of tests carried out in a greenhouse, the compounds of the present invention listed in the Table below were each sprayed in accordance with the pre-emergence method at a rate of application of 5 kg of active substance per hectare, emulsified in 600 litres of water per hectare, on to
Brassica and Solanum as the test plants. 3 weeks after the treatment the results thereof were evaluated and expressed by a numerical scale extending from 0 to 4, the value 0 representing no action and the value 4 representing destruction of the plant.
As will be seen from the Table, destruction of the test plants was achieved.
Compound of the invention Solanum Brassica 4-Fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) este
= Ct: Ct: 0 0 Ct: Ct: 0 Ct: . C 8O/4sou!t8s3 o o o o 8!JeJaS o o o o z?autodl smJau8J8Wbt o invention o o o N-Ethy 1-3-fl uorocarbani Ii C acid (3-ethoxycarbony I aminophenyl) ester 10 10 10 19 0 0 0 0 e3!tl acid (3-methoxycarbonyl- o. o 10 10 o o aminophenyl) ester N-Ethyl-3-f I uorocarban i I ic acid [3-(lmethylethoxy ez!ew ester 10 N-Ethy 1-4-fl uorocarbani Ii c acid t3-( 1-methyl ethoxy UO}103 no)-pheny Fizzester 10 10 10 O I O O nU punOE) v o o ov :,, cz xS xS c o o o 8 8 S ,C U X (D O cs co ,n, ,^ xn n r r a) ~ c C Ue > eC o to O o Q O Q E iJI ilCI ill 9 [lJ n, O z uE z sa z (u z <
C C N 0 Cr Agents for comparison 0 Do2Vso8?V2 O O O O D?2D}aS X O s O Dawodl v ur ua o snyuolo2u6 (s, cu I pheny N )-carbamoy X orO carbamate (according to German Patent Specification No.
1,567151) 10 1 2 10 6 1 3 6 3-Oh loro-4-f luorocarban " ic acid 0, phenyl) ester (according to German Patent Specification No. 2,638,897) 5 10 10 2 5 8 10 3,4-Difluorocarbanilic acid (3-ethoxycarbonylamino phenyl) ester (according to German 0, No. 2,638,897) 4 10 10 3 5 7 10 Untreated 10 10 10 10 10 10 10 10 0 = total ly uz t o nu-punolt action. nz c o o' Q o E < O 0' o X 8 O ç E 0 > ( > c D c oQ ns (a x U > 8 c a E a) E .
X Y > D E '~ a) E rz s . Z seI e o a) C O ia X c ( O SN 2 > O O a) a) O i o t ,@c Hs 11 11 < 2 0- CO Z (t QZ D O
Claims (115)
1. A diurethane of the general formula I
in which R1 represents a C1-C4-alkyl or phenylethyl group,
R2 represents a C1-C4-alkyl, halogeno-C1-C4-alkyl, C2-C4-alkenyl, halogeno-C2-C4-alkenyl, C2-C4-a Ikynyl or ha logeno-C2-C4-a Ikynyl group,
Y represents a hydrogen or fluorine atom and
X represents an oxygen or sulphur atom.
2. A compound as claimed in claim 1, wherein
R, represents a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl or 2-phenylethyi group and R2 represents a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl, allyl, propargyl, chlorethyl, 1-chloromethylethyl, 4-chlorobutynyl, 1-methylpropynyl or 4-chlorobutenyl group.
3. N-Ethyl-3-fluorocarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
4. 3-Fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester.
5. N-Ethyl-3-fluorocarbani!ic acid (3-methoxycarbonylaminophenyl) ester.
6. N-Ethyl-3-fluorocarbanilic acid [3-(methylthiocarbonylamiho)-phenyl] ester.
7. 4-Fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester.
8.4-Fluoro-N-methylcarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester.
9. N-Ethyl-4-fluorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester.
10. N-Ethyl-4-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester.
11. N-ethyl-4-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester.
12. N-Ethyl-3-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester.
13. 3-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester.
14. 3-Fluoro-N-methylcarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester.
15. 3-Fluoro-N-methylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
16. 4-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester
17.4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylaminophenyl) ester.
18. 4-Fluoro-N-(2-phenviethyl)-carbanilic acid (3-ethoxycarbonylaminophenyl) ester
19. N-Ethyl-3-fluorocarbanilic acid [3-(1 -methylethoxycarbonylamino)-phenyl] ester.
20. N-ethyl-4-fluorocarbanilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl] ester.
21. 4-Fluoro-N-methylcarbanilic acid [3-(1-methylethoxycarbonylamino)-phenyl] ester.
22. N-Ethyl-4-flu orocarba nilic acid [3-(ethylthioca rbonyla mino)-phenyl] ester.
23. 4-Fluoro-N-methylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
24. 3-Fluoro-N-methylcarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl] ester.
25. N-ethyl-3-fluorocarbanilic acid [3-(2-propynyloxyca rbonyla mino)-phenyl] ester.
26. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
27. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl] ester.
28. N-Ethyl-4-fluorocarbanilic acid (3-allyloxycarbonylaminophenyl) ester.
29. N-Ethyl-4-fluorocarbanilic acid [3-(2-propynyloxycarbonyla mino)-phenyl] ester.
30. 4-Fluoro-n-(2-phenylethyl)-carbanilic acid (3-allyloxycarbonylaminophenyl) ester.
31. 3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylaminophenyl) ester.
32. N-Ethyl-2-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester.
33. N-Ethyi-3,4-difluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester.
34. 3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxycarbonylaminophenyl) ester.
35. 3-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
36. 3-Fluoro-N-methylcarbanilic acid [3-(1-methylethoxycarbonylamino)-phenyl] ester.
37. 3-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester.
38. 3-Fluoro-N-ethylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester.
39. 4-Fluoro-N-methylcarbanilic acid (3-al lyloxycarbonylaminophenyl) ester.
40. N-ethyl-3-fluorocarbanilic acid [3-( 1 -ch loromethylethoxyca rbonyla mino)-phenyl] ester.
41. N-Ethyl-3 ,4-difluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester.
42. N-Ethyl-3,4-difluorncarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester.
43. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylaminophenyl) ester.
44. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxycarbonylaminophenyl) ester.
45. 2-Fiuoro-N-(2-phenylethyl)-carbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester.
46. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
47. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl] ester.
48. 2-Fluoro-N-(2-phenylethyl)-ca rba nilic acid [3-(2-propynyloxyca rbonyla mino)-phenyl] ester.
49. 3-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) ester.
50. 3-Fluoro-N-propylcarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester.
51. 3-Fluoro-N-propylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester.
52. N-Ethyl-3-fluorocarbanilic acid [3-( 1 -methyl-2-propenyloxycarbonylamino)-phenyl] ester.
53. N-Ethyl-2-fluorocarbanilic acid [3-(1-methyl-2-propenyloxycarbonylamino)-phenyl] ester.
54. N-Ethyl-4-fluorocarbanilic acid [3-( 1 -methyl-2-propenyloxycarbonylamino)-phenyl] ester.
55. N-Butyl-3-fluorocarbanilic acid (3-methoxyca rbonylaminophenyl) ester.
56. 3-Fluoro-N-methylcarbanilic acid [3-(2-methylpropoxycarbonylamino)-phenyl] ester.
57. 4-Fluoro-N-(2-phenylethyl)-carba nilic acid [3-( 1 -methyl-2-propenyloxycarbonylamino)- phenyl] ester.
58. 3-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(1 -methyl-2-propenyloxycarbonylamino)phenyl] ester.
59. 3-Fluoro-N-methylcarbanilic acid [3-(1-methyl-2-propenyloxycarbonylarnino)-phenyl] ester.
60. 4-Fluoro-N-methylcarbanilic acrid t3-(1 -methyl-2-propenyloxyca rbonylamino)-phenyl] ester.
61. N-Butyl-4-fluorocarbanilic acid [3-( 1 -methyl-2-propenyloxycarbonylamino)-phehyl] ester.
62. 4-Fluoro-N-methylcarbanilic acid [3-(2-methylpropoxycarbonylamino)-phenyl] ester.
63. 4-Fluoro-N-propylcarbanilic acid [3-( 1 -methyl-2-propenyloxycarbonylamino)-phenyl] ester.
64. 2-Fluorn-N-(2-phenylethyl)-carbanilic acid [3-(2-methylpropoxycarbonylamino)-phenyl] ester.
65. 4-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) ester.
66. 4-Fluoro-N-propylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester.
67. N-Butyl-4-fluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester.
68. N-Butyl-4-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester.
69. 4-Fluoro-N-butylcarbanilic acid [3-(1 -methylethoxycarbonylamino)-phenyl] ester.
70. 4-Fluoro-N-butylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
71. N-Butyl-4-fluorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl] ester.
72. 4-Fluoro-N-propylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
73. 4-Fluoro-N-propylcarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl] ester.
74. N-Butyl-4-fiuoroca rbanilic acid [3-(methylthiocarbonyla mi no)-phenyl] ester.
75. N-Ethyl-2-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester.
76. N-Ethyl-2-fluorocarbanilic acid [3-(methylthiocarbonyla mino)-phenyl] ester.
77. N-Ethyl-2-fluorocarbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
78. N-Ethyl-2-fluorocarbanilic acid [3-(1 -methylethoxycarbonylamino)-phenyl] ester.
79. N-ethyl-2-fluoroca rbanilic acid [3-(2-propynyloxyca rbonyla mino)-phenyl] ester.
80. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyloxycarbonylaminophenyl) ester.
81. A process for the manufacture of a compound of the general formula I given in claim 1, in which RX, R2, Y and X have the meanings given in claim 1, wherein
(a) a compound of the general formula
in which Rz and X have the meanings given above, is reacted in the presence of an acid acceptor with an amine of the general formula
in which P1 and Y have the meanings given above, or
(b) a compound of the general formula
in which R2 and X have the meanings given above, is reacted in the presence of a tertiary organic base or is reacted in the form of an alkali salt thereof with a carbamoyl chioride of the general formula
in which R1 and Y have the meanings given above, each reaction being carried out at a temperature within the range of from 0 to 100 C, or
(c) a nitro compound of the general formula
in which R and Y have the meanings given above, is catalytically hydrogenated to form the corresponding amino compound which is then reacted in the presence of an acid acceptor with a compound of the general formula CI-C0-X-R2, in which R2 and X have the meanings given above.
82. A process as claimed in claim 81, conducted substantially as described herein.
83. A process as claimed in claim 81, conducted substantially as described in Example 1 herein.
84. A herbicidal preparation which comprises a compound of the general formula I given in claim 1, in which R1, R2, Y and have the meanings giver) in claim 1, in admixture or conjunction with suitable carrier.
85. A herbicidal preparation which comprises a compound as claimed in claim 2, in admixture or conjunction with a suitable carrier.
86. A herbicidal preparation which comprises the compound claimed in any one of claims 5, 1 1, 12, 1 6, 1 9, 20, 21, 32, 36 and 41, in admixture or conjunction with a suitable carrier.
87. A herbicidal preparation which comprises the compound claimed in any one of claims 3, 4. 6 to 10, 13 to 1 5, 17, 18,22 to 31, 33 to 35, 37 to 40 and 42 to 80, in admixture or conjunction with a suitable carrier.
88. A preparation as claimed in any one of claims 84 to 87, which is in the form of a powder, a strewable preparation, granules, a solution, an emulsion or a suspension.
89. A preparation as claimed in any one of claims 84 to 88, containing a single compound of the general formula 1.
90. A preparation as claimed in any one of claims 84 to 88, containing two or more compounds of the general formula
91. A preparation as claimed in any one of claims 84 to 90, which also contains one or more active substances selected from plant-protecting agents, pesticides and herbicides other than compounds of the general formula I.
92. A preparation as claimed in any one of claims 84 to 91, wherein the total amount present of active substance or substances is appcoximately 5 to 95% by weight.
93. A preparation as claimed in any one of claims 84 to 92, containing a single surface-active agent in an amount of up to 20% by weight.
94. A preparation as claimed in any one of claims 84 to 92, containing two or more surface-active agents in a total amount of up to 20% by weight.
95. Any one of the herbicidal preparations as claimed in claim 84 and substantially as described in any one of Examples 2 to 4 herein.
96. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound of the general formula I given in claim 1, in which R1, R2, Y and X have the meanings given in claim 1.
97. A method as claimed in claim 96, wherein.the area is treated with a compound as claimed in claim 2.
98. A method as claimed in claim 96, wherein the area is treated with a compound claimed in any one of claims 1 1. 12, 16, 19,20,21,32,36and41.
99. A method as claimed in claim 96, wherein the area is treated with the compound claimed in anyoneofclaims3,4,6to10,13to15,17,18,22to31,33to35,37to40and42to80.
100. A method as claimed in claim 96, wherein the area is treated with a herbicidal preparation as claimed in any one of claims 84 to 95.
101. A method as claimed in any one of claims 96 to 100, wherein a single compound of the general formula I is used for the treatment in an amount within the range of from 1 to 5 kg per hectare.
102. A method as claimed in any one of claims 96 to 100, wherein two or more compounds of the general formula I are used for the treatment in a total amount within the range of from 1 to 5 kg per hectare.
103. A method as claimed in claim 96, conducted substantially as described in Example 4 herein.
104. A method of protecting a crop area against weeds, wherein the crop area is treated with a compound of the general formula I given in claim 1, in which R, R2,Y and X have the meanings given in claim 1.
105. A method as claimed in claim 104, wherein the crop area is treated with a compound as claimed in claim 2.
106. A method as claimed in claim 104, wherein the crop area is treated with the compound claimed in any one of claims 5, 1 1, 12. 16, 19,20,21,32,36and41.
107. A method as claimed in claim 104, wherein the crop area is treated with the compound claimed in any one of claims 3, 4,6 to 10, to 15,17, to 31,33 to 35,37 to 40 and 42 to 80.
108. A method as claimed in claim 1 04, wherein the crop area is treated with a herbicidal preparation as claimed in any one of claims 84 to 95.
109. A method as claimed in any one of claims 104 to 108, wherein a single compound of the general formula I is used for the treatment in an amount within the range of from 1 to 5 kg per hectare.
110. A method as claimed in any one of claims 104 to 108, wherein two or more compounds of the general formula I are used for the treatment in a total amount within the range of from 1 to 5 kg per hectare.
111. A method as claimed in any one of claims 104 to 110, wherein the crop is a cotton crop.
112. A method as claimed in any one of claims 104 to 110, wherein the crop is a soya, groundnut, potato, maize, rice, sorghum or cereal crop.
113. A pack which comprises a compound of the general formula I given in claim 1, in which R1,
R2, Y and X have the meanings given in claim 1, together with instructions for its use as a herbicide.
114. A pack as claimed in claim 113, wherein the compound of the general formula I is a compound as claimed in claim 2.
115. A pack as claimed in claim 113, wherein the compound of the general formula I is the compound claimed in any one of claims 5, 11, 12, 16, 19, 20, 21,32, 36 and 41.
11 6. A pack as claimed in claim 113, wherein the compound of the general formula I is the compound claimed in any one of claims 3, 4, 6to 10, 13to 15,17, 18,22to31,33to35,37to40 and 42 to 80.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792901658 DE2901658A1 (en) | 1979-01-15 | 1979-01-15 | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2040939A true GB2040939A (en) | 1980-09-03 |
| GB2040939B GB2040939B (en) | 1983-07-27 |
Family
ID=6060757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8001303A Expired GB2040939B (en) | 1979-01-15 | 1980-01-15 | Hericidally active diurethanes and their manufacture and use |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5823865B2 (en) |
| AR (1) | AR224143A1 (en) |
| AT (1) | AT365411B (en) |
| AU (1) | AU532736B2 (en) |
| BE (1) | BE881152A (en) |
| BG (2) | BG31465A3 (en) |
| BR (1) | BR8000161A (en) |
| CA (1) | CA1128061A (en) |
| CH (1) | CH645343A5 (en) |
| CS (1) | CS212336B2 (en) |
| DD (1) | DD148709A5 (en) |
| DE (1) | DE2901658A1 (en) |
| DK (1) | DK16380A (en) |
| EG (1) | EG14116A (en) |
| ES (1) | ES487720A1 (en) |
| FI (1) | FI794081A (en) |
| FR (1) | FR2446275A1 (en) |
| GB (1) | GB2040939B (en) |
| GR (1) | GR71679B (en) |
| HU (1) | HU181682B (en) |
| IL (1) | IL59126A (en) |
| IN (1) | IN153545B (en) |
| IT (1) | IT1130864B (en) |
| MA (1) | MA18702A1 (en) |
| MX (1) | MX5743E (en) |
| NL (1) | NL8000112A (en) |
| PH (1) | PH15195A (en) |
| PL (1) | PL125248B1 (en) |
| PT (1) | PT70692A (en) |
| RO (1) | RO79454A (en) |
| SE (1) | SE8000278L (en) |
| SU (1) | SU942587A3 (en) |
| TR (1) | TR20529A (en) |
| YU (1) | YU1180A (en) |
| ZA (1) | ZA80244B (en) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567151C3 (en) * | 1965-04-09 | 1974-02-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diurethanes, processes for the preparation of these compounds and herbicidal compositions containing them |
| US3535101A (en) * | 1966-09-07 | 1970-10-20 | Schering Ag | Herbicide and algicide means |
| US3901936A (en) * | 1966-10-15 | 1975-08-26 | Schering Ag | Process for the preparation of n-carbamoyloxyphenyl carbamates |
| DE2413933A1 (en) * | 1974-03-20 | 1975-09-25 | Schering Ag | DIURETHANE WITH SELECTIVE HERBICIDAL EFFECT |
| JPS5140073A (en) * | 1974-06-28 | 1976-04-03 | Siemens Ag | SHIRIKONNODOOPINGUHOHO |
| DE2557552C2 (en) * | 1975-12-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Diurethanes and herbicidal agents containing these compounds as active ingredients |
| DE2638897C2 (en) | 1976-08-28 | 1978-10-26 | Basf Ag, 6700 Ludwigshafen | Diurethanes and herbicides containing them |
| DE2650796A1 (en) * | 1976-11-03 | 1978-05-11 | Schering Ag | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDAL PRODUCT CONTAINING THEM |
-
1979
- 1979-01-15 DE DE19792901658 patent/DE2901658A1/en not_active Withdrawn
- 1979-12-24 IN IN940/DEL/79A patent/IN153545B/en unknown
- 1979-12-28 FI FI794081A patent/FI794081A/en not_active Application Discontinuation
-
1980
- 1980-01-03 YU YU00011/80A patent/YU1180A/en unknown
- 1980-01-08 NL NL8000112A patent/NL8000112A/en not_active Application Discontinuation
- 1980-01-10 TR TR20529A patent/TR20529A/en unknown
- 1980-01-11 DD DD80218424A patent/DD148709A5/en unknown
- 1980-01-11 AT AT0013980A patent/AT365411B/en not_active IP Right Cessation
- 1980-01-11 MX MX808584U patent/MX5743E/en unknown
- 1980-01-11 SU SU802867755A patent/SU942587A3/en active
- 1980-01-11 PH PH23505A patent/PH15195A/en unknown
- 1980-01-12 EG EG21/80A patent/EG14116A/en active
- 1980-01-14 SE SE8000278A patent/SE8000278L/en not_active Application Discontinuation
- 1980-01-14 IT IT19194/80A patent/IT1130864B/en active
- 1980-01-14 GR GR60957A patent/GR71679B/el unknown
- 1980-01-14 HU HU8063A patent/HU181682B/en unknown
- 1980-01-14 MA MA18899A patent/MA18702A1/en unknown
- 1980-01-14 BG BG8046235A patent/BG31465A3/en unknown
- 1980-01-14 IL IL59126A patent/IL59126A/en unknown
- 1980-01-14 BG BG8046234A patent/BG31495A3/en unknown
- 1980-01-14 RO RO8099869A patent/RO79454A/en unknown
- 1980-01-14 PL PL1980221361A patent/PL125248B1/en unknown
- 1980-01-14 PT PT70692A patent/PT70692A/en unknown
- 1980-01-14 CA CA343,600A patent/CA1128061A/en not_active Expired
- 1980-01-15 CS CS80312A patent/CS212336B2/en unknown
- 1980-01-15 GB GB8001303A patent/GB2040939B/en not_active Expired
- 1980-01-15 ZA ZA00800244A patent/ZA80244B/en unknown
- 1980-01-15 AU AU54604/80A patent/AU532736B2/en not_active Ceased
- 1980-01-15 DK DK16380A patent/DK16380A/en not_active Application Discontinuation
- 1980-01-15 AR AR279638A patent/AR224143A1/en active
- 1980-01-15 CH CH32280A patent/CH645343A5/en not_active IP Right Cessation
- 1980-01-15 BE BE0/198971A patent/BE881152A/en not_active IP Right Cessation
- 1980-01-15 ES ES487720A patent/ES487720A1/en not_active Expired
- 1980-01-15 FR FR8000793A patent/FR2446275A1/en active Granted
- 1980-01-16 JP JP55002672A patent/JPS5823865B2/en not_active Expired
- 1980-09-10 BR BR8000161A patent/BR8000161A/en unknown
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