CA1128061A - Herbicidally active diurethanes and their manufacture and use - Google Patents
Herbicidally active diurethanes and their manufacture and useInfo
- Publication number
- CA1128061A CA1128061A CA343,600A CA343600A CA1128061A CA 1128061 A CA1128061 A CA 1128061A CA 343600 A CA343600 A CA 343600A CA 1128061 A CA1128061 A CA 1128061A
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- CA
- Canada
- Prior art keywords
- ester
- acid
- phenyl
- fluoro
- living plant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Novel diurethanes of the general formula I
(I) (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) and their manufacture. The novel compounds of the general formula I 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.
Novel diurethanes of the general formula I
(I) (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) and their manufacture. The novel compounds of the general formula I 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
l~Z8~61 The present invention is concerned with new diurethanes, with processes ~or theimanufactu~e c~ these compounds and with thier use as herbicidal ,a,gents, 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.
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 ac-tion 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
;
The problem upon which the present invention is based has been to develop a herbicidal agent which has a very good ac-tion 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
;
- 3 -O-CO~ ~ Y
. F ~I) ~ ~ X ~2 in which R represents a Cl-C4-alkyl or ~henylethyl group, -~
R2 representq a al-C4-alkyl, halogeno-Cl-C4-alk~yl9 C2-C4-alke~yl, halogeno-C2-C4-alkenyl, C2-C4-alkynyl or halogeno-C2-C4-alkynyl group, Y represents a hydrogen or ~luorine atom an~
repre~ents an oxygen or sulphur atom.
~ he compounds of the present i.nvention, surpri-~ingly, exhibit an outstanding tolerance in cotton crops which i3 not the case with known compounds ol analogous con~titution.
In addition, they have a very good action against weeds that are di~iicult to control, ~or example ~maranthu~, Stellaria, Matricaria and others, which can be controlled by both the pre-emergence and the post-emergence methodsO
Application quantities within the range o~ ~rom 1 to a maximum o~ 5 kg of active subqtance per hectare are generally su~ficient to control these seed weed~q, the . ~ .
- , -1~%~
compounds o~ the present invention exhibiting a selective action aleo in useful plant crops other than cotton, for example soya, ground-nut, potatoes, maize, rice, sorghum and cerealsO When two or more compounds of the present i~vention are used, the range o~ 1 to 5 kg refers of course to the total application quar,tities o~ these compounds.
The present inve~tion accordingly also provides a herbicidal preparation which comprises a compound o~ the ge~eral formula I, in admixture or conjunction with a suitable carrier. The preparation may of course contain one or more compounds o~ the general ~ormula Io The present invention further provides a method o~
protecting a living plant against weeds? wherein the area in the vicinity of the living plant is treated with a compourd of the general formula I.
~ he 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.
~ he present invention further provides a pack which compri~es a compound of the ~eneral formula I together ~ith instructions for it~ u~e as a herbicide.
~ he compounds of the present invention may be used either ~in6~1y or in the form of mixtures with one another or with other active substancesO If desired, other plant-protecting agents and/or pesticides may be added, dependin~ on the desired aimO
1128~!61 I~ a broadening o~ the range of action i~ intended, other herbicides may also be added. As suitable herbici-dally active co-components there may be mentioned, ~or example, active ~ub~tances ~rom the groups of triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carbo~ylic acid~ and halocarboxylic acids, substituted benzoic acids and aryloxycarboxylic acids, hydrazides, ~mides, nitriles, esters o~ such carboxylic acids, carbamic acid esters and thiocarbamic acid esters, ureas, 2,3,6-trichiorobenzylo~yisopropanol and thiocyanogen-containing agents.
Furthermore, other additives may also be used, for example non-phytotoxic additives which with herbiclde~
produce a synergistic increase in action, ~or example wetting agents, emulsifi.ers, solYents and oily additi~res.
. The active compounds of the present invention or mixtures contalning them are advan-tageously used in the form of herbicidal preparations, for example powders, strewable preparations, granule~ solution~, emuls.ions or suspen~ions, with the addition of liquid ~nd~or solid vehicle~ or diluents and, i~ desired, of surface-acti~e agents, for example wetting, adhesive, emulsifying and/or disper~ing auxiliary agent~.
Suitable liquid carrier~ are, for example, water, aliphatic hydrocarbons, aromatic hydrocarbons, for example benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide and dimethyl~ormamide, and also ~2~Q61 mineral oil fractions.
~ uitable solid carriers are, for example, mineral earth~, for example tonsil, silica gel, talcum9 kaolin, attaclay, limestone and ~ilicic acid, and vegetable products, for example meals.
As surface-active agents there may be mentioned, for exa~ple, calcium li~nin sulphonate~ polyoxyethylene-alkylphenol ethers, naphthalene~ulpho~ic acid~ and salts thereo~, phenolsulphonic acid~ and salt~ thereof, for-maldehyde condensatess fatty alcohol sulphates and also sub~tituted benzene~ulphonic acids and salts thereof.
The proportion of the active ~ubstance or sub~tances in the various herbicidal preparations may vary within wide limits. ~or example 9 the preparations may contai~
approximately 5 to 95% by weight OL active substanca(~), approximately 95 to 5~0 by weight of liquid or solid carrler and al~o, if desired, up to 20~o by weight of surface-active a~ent(s).
~ he active compounds may be applied in the usual manner, ~or example with water a~ the oarrier in spray liquor quantities o~ approximately 50 to 1000 litres/
hectare. It is al~o po~sible to apply the active com-pounds by the so-called low-volume and ultra-low-volume methods as well as to apply them in the form of ~o-called microgranules.
llZ~361 -- 7 ~
~ s group~ repre~ented by the ~ymbol Rl in the general ~ormula X there may be mentioned, for example, methyl, ethyl, propyl, i60propyl, butyl, isobutyl, ~ec.-butyl and 2-phenylethyl group~, and a~ groups represented by the ~ymbol R2, ~or e~ample, methyl, ethyl, propyl, i60propyl, butyl, isobutyl, sec.-butyl, allyl, propargyl, chlorethyl, l-chloromethylethyl, 4-chlorobutynyl, 1-methylpropynyl and 4-chlorobutenyl ~roup~. -Compounds o~ the present invention which aredistin~uished by an out~tanding selective herbicidal action are especially N-ethyl-3-Iluorocarbanilic acid (3-etho~ycarbonylaminophenyl) ester, N-ethyl-3-~luoro-carbanilic acid (3-metho~ycarbonylaminophenyl) ester, N-ethyl-3-~luorocarbanilic acid C3-(1-methyleth~oxycarbony~-ami.lo)-phenyl] e~ter, N-ethyl-4-fluorocarbanilic acid (3-ethoxycarborlylaminophenyl) ester, 4-fluoro-N-methylcar-banilic acid (3-ethoxycarbonvlaminophenyl) ester, N-ethyl-3-fluorocarbanilic acid ~3-(1-methylethoxycarbonyl-amino)-phenylJ est~r, ~-othyl-4-fluorocarbanilic acid ~ methylethoxycarbonylamino)-phen~rl] ester, 4-fluoro-N-methylcarbanilic acid ~3~ methylethoxycarbonyl~nino)-phenyl] ester, 3-~luoro-I~-methylcarbanilic acid [3-(1-methylethoxycarbonylamino)-phenyl] e6ter, N-ethy1-3,4-difluorocarbanilic acid (3-ethoxycarbonylaminophenyl) e~ter and N-ethyl-2-~luorocarbanilic acid ~3-methoxycar-bonylaminophenyl) ester.
~L28~i6~1L
The new compo~lds of the general formula I may be manufactured, for example, by the process o~ the - present invention, as dePined 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 formula O-CO-~l ~ ~-CO-~-~2 in which R2 and X have the meanings given abo~e, is reacted with an amine of the general formula Y
F
in which Rl and Y have the meanings given abo~e, in the pre~ence o~ an aci.d acceptor, ~or examp].e with the addition of an excess of the amine or of an inorganic base, for e~ample a sodium hydroxide solution, sodium carbonate or potassium carbonate, or a tertiary organic base, for e~ample triethylamine, or b) a compound of the general formula 1~28~61 CO-~-R2 in which R2 and X have the meanings ~iven above, is reacted in the presence o~ a tertiary organic base, for example triethylamine or pyridine, or is reacted in the ~o~m of an alkali salt thereof with a carbamoyl c~iloride o~ the general formula ~ N-aO-Cl, ~?
in whlch ~ and Y have ~he meaning~ given above, each reaation being carried out at a temperature withil the range of from 0 to 100C, or c) a nitro compound o~ the general ~ormula l~Z8~6~
o_ao~
~ ~ F
1~ N02 i21 which ~ and Y have the meanings given above, is catalytically hydrogenated, ~or example by using nickel in methanol, to fo~m the corresponding amino compound which is then reacted with a compound of the general formula Cl-CO-~-R2 in ~hich R2 ~nd X have the meanings given above, in the presence of an acid acceptor, *or example an inorganic base, ~or example a ~odium hydroxide solution, ~odium carbo~ate or potassium carbonate, or a tertiary organic ba_e~ ~or e~ample trie~hy~ ine.
The compounds of the ~eneral formula I formed by any one of t~e variants (a) to (c) may be isolated in ~he usual man~er.
~ he compou~ds o~ the present i~lvention are soluble in acetone, cyclohexanone, i~ophorone, tetrahydrofuran, dimethylformamide, dimethyl sulphoxide and ethyl acetate.
~3.28~
~ he ~ollowing E~ample~ illu~trate the inventionO
Example 1 illustrates the manu~acture of the compounds of the present lnvention and Examples 2 to 4 illustrate the po~ible way~ o~ using the compounds o~ the present invention and, in the case of Example 4, compares their herbicidal action with that o~ k~o~m compounds.
~5~ ~
N-~thyl-3-fluorocarbanilic acid t3-(ethylthiocarbon~l-amino)-phenyl] ester ~ o a solution oP 13~9 g (0.1 mole) of N-ethyl-3-fluoroaniline in 70 ml of ethyl acetate there were added dropwi~e, while stirring and cooling to 10 to 15C, a ~olution o~ 26.0 g (0.1 mole) of chlorofor~ic acid C3-(ethylthiocarbcnylamino)-phenyl] ester in 70 ml o~ ethyl acetate and, at the same time, a solution o* 13.8 g (0.1 mole) of potassium carbor.ate in 50 ml of w~ter~ ~tirr~ng wa~ continued for 30 minutes at 15C, and the organic phase was thon separated and, with the addition of ice, washed with dilute hydroc~ilorio acid ~ld water. After drying with magnesium sulphate, the mixture wa8 concen-trated by evaporation under reduced pressure. The residue after evaporation was recrystallized from ethyl acetate/pentane.
Yield: 29~4 g - 81~ o~ the theoretical yield of ~-ethyl-~3-fluorocarbanilic acid ~-(ethylthio-carbonylami~o)-phenyl] ester.
l~Z8~6 M.p.: 127~.
~ he ~ollowing compounds of the present invention may be manu~actured in an analogous manner.
Name of the compound Physical Constant . .
3-~luoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester M~p.: 105-107C
N-Eth~1-3-~luorocarbanilic acid (3- O
methoxycarbonylaminophelly].) ester Mopo 108-109 C
~thyl-3-fluorocarbanilic acid [3-(methylthiocarbonyla~i~o)-phenyl~ O
ester Mop~ 125-127 a ~-Fluoro-N~methylcarbanilic acid (3-methoxycarbonylaminophenyl) e~ter M.p.: 96-97C
. F ~I) ~ ~ X ~2 in which R represents a Cl-C4-alkyl or ~henylethyl group, -~
R2 representq a al-C4-alkyl, halogeno-Cl-C4-alk~yl9 C2-C4-alke~yl, halogeno-C2-C4-alkenyl, C2-C4-alkynyl or halogeno-C2-C4-alkynyl group, Y represents a hydrogen or ~luorine atom an~
repre~ents an oxygen or sulphur atom.
~ he compounds of the present i.nvention, surpri-~ingly, exhibit an outstanding tolerance in cotton crops which i3 not the case with known compounds ol analogous con~titution.
In addition, they have a very good action against weeds that are di~iicult to control, ~or example ~maranthu~, Stellaria, Matricaria and others, which can be controlled by both the pre-emergence and the post-emergence methodsO
Application quantities within the range o~ ~rom 1 to a maximum o~ 5 kg of active subqtance per hectare are generally su~ficient to control these seed weed~q, the . ~ .
- , -1~%~
compounds o~ the present invention exhibiting a selective action aleo in useful plant crops other than cotton, for example soya, ground-nut, potatoes, maize, rice, sorghum and cerealsO When two or more compounds of the present i~vention are used, the range o~ 1 to 5 kg refers of course to the total application quar,tities o~ these compounds.
The present inve~tion accordingly also provides a herbicidal preparation which comprises a compound o~ the ge~eral formula I, in admixture or conjunction with a suitable carrier. The preparation may of course contain one or more compounds o~ the general ~ormula Io The present invention further provides a method o~
protecting a living plant against weeds? wherein the area in the vicinity of the living plant is treated with a compourd of the general formula I.
~ he 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.
~ he present invention further provides a pack which compri~es a compound of the ~eneral formula I together ~ith instructions for it~ u~e as a herbicide.
~ he compounds of the present invention may be used either ~in6~1y or in the form of mixtures with one another or with other active substancesO If desired, other plant-protecting agents and/or pesticides may be added, dependin~ on the desired aimO
1128~!61 I~ a broadening o~ the range of action i~ intended, other herbicides may also be added. As suitable herbici-dally active co-components there may be mentioned, ~or example, active ~ub~tances ~rom the groups of triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carbo~ylic acid~ and halocarboxylic acids, substituted benzoic acids and aryloxycarboxylic acids, hydrazides, ~mides, nitriles, esters o~ such carboxylic acids, carbamic acid esters and thiocarbamic acid esters, ureas, 2,3,6-trichiorobenzylo~yisopropanol and thiocyanogen-containing agents.
Furthermore, other additives may also be used, for example non-phytotoxic additives which with herbiclde~
produce a synergistic increase in action, ~or example wetting agents, emulsifi.ers, solYents and oily additi~res.
. The active compounds of the present invention or mixtures contalning them are advan-tageously used in the form of herbicidal preparations, for example powders, strewable preparations, granule~ solution~, emuls.ions or suspen~ions, with the addition of liquid ~nd~or solid vehicle~ or diluents and, i~ desired, of surface-acti~e agents, for example wetting, adhesive, emulsifying and/or disper~ing auxiliary agent~.
Suitable liquid carrier~ are, for example, water, aliphatic hydrocarbons, aromatic hydrocarbons, for example benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide and dimethyl~ormamide, and also ~2~Q61 mineral oil fractions.
~ uitable solid carriers are, for example, mineral earth~, for example tonsil, silica gel, talcum9 kaolin, attaclay, limestone and ~ilicic acid, and vegetable products, for example meals.
As surface-active agents there may be mentioned, for exa~ple, calcium li~nin sulphonate~ polyoxyethylene-alkylphenol ethers, naphthalene~ulpho~ic acid~ and salts thereo~, phenolsulphonic acid~ and salt~ thereof, for-maldehyde condensatess fatty alcohol sulphates and also sub~tituted benzene~ulphonic acids and salts thereof.
The proportion of the active ~ubstance or sub~tances in the various herbicidal preparations may vary within wide limits. ~or example 9 the preparations may contai~
approximately 5 to 95% by weight OL active substanca(~), approximately 95 to 5~0 by weight of liquid or solid carrler and al~o, if desired, up to 20~o by weight of surface-active a~ent(s).
~ he active compounds may be applied in the usual manner, ~or example with water a~ the oarrier in spray liquor quantities o~ approximately 50 to 1000 litres/
hectare. It is al~o po~sible to apply the active com-pounds by the so-called low-volume and ultra-low-volume methods as well as to apply them in the form of ~o-called microgranules.
llZ~361 -- 7 ~
~ s group~ repre~ented by the ~ymbol Rl in the general ~ormula X there may be mentioned, for example, methyl, ethyl, propyl, i60propyl, butyl, isobutyl, ~ec.-butyl and 2-phenylethyl group~, and a~ groups represented by the ~ymbol R2, ~or e~ample, methyl, ethyl, propyl, i60propyl, butyl, isobutyl, sec.-butyl, allyl, propargyl, chlorethyl, l-chloromethylethyl, 4-chlorobutynyl, 1-methylpropynyl and 4-chlorobutenyl ~roup~. -Compounds o~ the present invention which aredistin~uished by an out~tanding selective herbicidal action are especially N-ethyl-3-Iluorocarbanilic acid (3-etho~ycarbonylaminophenyl) ester, N-ethyl-3-~luoro-carbanilic acid (3-metho~ycarbonylaminophenyl) ester, N-ethyl-3-~luorocarbanilic acid C3-(1-methyleth~oxycarbony~-ami.lo)-phenyl] e~ter, N-ethyl-4-fluorocarbanilic acid (3-ethoxycarborlylaminophenyl) ester, 4-fluoro-N-methylcar-banilic acid (3-ethoxycarbonvlaminophenyl) ester, N-ethyl-3-fluorocarbanilic acid ~3-(1-methylethoxycarbonyl-amino)-phenylJ est~r, ~-othyl-4-fluorocarbanilic acid ~ methylethoxycarbonylamino)-phen~rl] ester, 4-fluoro-N-methylcarbanilic acid ~3~ methylethoxycarbonyl~nino)-phenyl] ester, 3-~luoro-I~-methylcarbanilic acid [3-(1-methylethoxycarbonylamino)-phenyl] e6ter, N-ethy1-3,4-difluorocarbanilic acid (3-ethoxycarbonylaminophenyl) e~ter and N-ethyl-2-~luorocarbanilic acid ~3-methoxycar-bonylaminophenyl) ester.
~L28~i6~1L
The new compo~lds of the general formula I may be manufactured, for example, by the process o~ the - present invention, as dePined 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 formula O-CO-~l ~ ~-CO-~-~2 in which R2 and X have the meanings given abo~e, is reacted with an amine of the general formula Y
F
in which Rl and Y have the meanings given abo~e, in the pre~ence o~ an aci.d acceptor, ~or examp].e with the addition of an excess of the amine or of an inorganic base, for e~ample a sodium hydroxide solution, sodium carbonate or potassium carbonate, or a tertiary organic base, for e~ample triethylamine, or b) a compound of the general formula 1~28~61 CO-~-R2 in which R2 and X have the meanings ~iven above, is reacted in the presence o~ a tertiary organic base, for example triethylamine or pyridine, or is reacted in the ~o~m of an alkali salt thereof with a carbamoyl c~iloride o~ the general formula ~ N-aO-Cl, ~?
in whlch ~ and Y have ~he meaning~ given above, each reaation being carried out at a temperature withil the range of from 0 to 100C, or c) a nitro compound o~ the general ~ormula l~Z8~6~
o_ao~
~ ~ F
1~ N02 i21 which ~ and Y have the meanings given above, is catalytically hydrogenated, ~or example by using nickel in methanol, to fo~m the corresponding amino compound which is then reacted with a compound of the general formula Cl-CO-~-R2 in ~hich R2 ~nd X have the meanings given above, in the presence of an acid acceptor, *or example an inorganic base, ~or example a ~odium hydroxide solution, ~odium carbo~ate or potassium carbonate, or a tertiary organic ba_e~ ~or e~ample trie~hy~ ine.
The compounds of the ~eneral formula I formed by any one of t~e variants (a) to (c) may be isolated in ~he usual man~er.
~ he compou~ds o~ the present i~lvention are soluble in acetone, cyclohexanone, i~ophorone, tetrahydrofuran, dimethylformamide, dimethyl sulphoxide and ethyl acetate.
~3.28~
~ he ~ollowing E~ample~ illu~trate the inventionO
Example 1 illustrates the manu~acture of the compounds of the present lnvention and Examples 2 to 4 illustrate the po~ible way~ o~ using the compounds o~ the present invention and, in the case of Example 4, compares their herbicidal action with that o~ k~o~m compounds.
~5~ ~
N-~thyl-3-fluorocarbanilic acid t3-(ethylthiocarbon~l-amino)-phenyl] ester ~ o a solution oP 13~9 g (0.1 mole) of N-ethyl-3-fluoroaniline in 70 ml of ethyl acetate there were added dropwi~e, while stirring and cooling to 10 to 15C, a ~olution o~ 26.0 g (0.1 mole) of chlorofor~ic acid C3-(ethylthiocarbcnylamino)-phenyl] ester in 70 ml o~ ethyl acetate and, at the same time, a solution o* 13.8 g (0.1 mole) of potassium carbor.ate in 50 ml of w~ter~ ~tirr~ng wa~ continued for 30 minutes at 15C, and the organic phase was thon separated and, with the addition of ice, washed with dilute hydroc~ilorio acid ~ld water. After drying with magnesium sulphate, the mixture wa8 concen-trated by evaporation under reduced pressure. The residue after evaporation was recrystallized from ethyl acetate/pentane.
Yield: 29~4 g - 81~ o~ the theoretical yield of ~-ethyl-~3-fluorocarbanilic acid ~-(ethylthio-carbonylami~o)-phenyl] ester.
l~Z8~6 M.p.: 127~.
~ he ~ollowing compounds of the present invention may be manu~actured in an analogous manner.
Name of the compound Physical Constant . .
3-~luoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester M~p.: 105-107C
N-Eth~1-3-~luorocarbanilic acid (3- O
methoxycarbonylaminophelly].) ester Mopo 108-109 C
~thyl-3-fluorocarbanilic acid [3-(methylthiocarbonyla~i~o)-phenyl~ O
ester Mop~ 125-127 a ~-Fluoro-N~methylcarbanilic acid (3-methoxycarbonylaminophenyl) e~ter M.p.: 96-97C
4-~luoro-N-methylcarbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester M.p.: 106-108C
N-Ethyl-4-~luorocarbanilic acid ~3-(methylthioca~bo~yla~ino)-phenyl] ester M.p.: 143-144C
N-Ethyl-4 ~luorocarbanilic acid (3-~ethoxycarbonyl~inophenyl) est~r M.p.: 117-118C
N-~thyl-4-~luorocarbanilic acid (3-ethoxycarbonylamillophenyl) ester M.p.: 76-7'la thyl-3-~luorocarbanilic acid (3-ethoxycarbonylaminophenyl) est~r M~po 122C
3-~luoro-N-methylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester Mopo 91-92C
~-~luoro-N-methylcarbanilic acid [3-(methylthiocarbonylamino)-phenyl~ ester ~I~po 116C
~-~luoro-N-methylcarbanilic acid ~3-(ethylthiocarbonylamino)-phenyl] ester M.p.: 124-125C
1~28~61 .
Name of the compound Phy~ical Constant 4-~luoro~N-methylcarbanilic acid (3~ 20 ethoxycarbonylaminophenyl) ester nD : 1.5472 4-~luoro-~-(2-phe~ylethyl)-carbanilic acid (3-methoxycarbonyl~ninophenyl) 0 ester M.p.: 137 C
4-Fluoro-N (2-phenylethyl)-carbanilic acid (3~ethoxycarbonylaminophenyl) O
es-ter M~p.: 103-104 C
N-~thyl-3-fluorocarbanilic acid t3-(1 ~ethylethoxycarbonylamino)-phenyl] ester M~po 98C
h~-Ethyl-4-fluorocarbanilic acid C~-(l-methylethoxycarbo~yl~nino) phenylJ
ester M~po 84-86C .
4-~luoro-~-methylcarbanilic acid C3-(l~methylethoxycarbonyla~ino)- O
phenyl] ester M.p.: 88 C
N-~thyl-4-fluorocarbanilic acid ~3-(ethylthiocarbonyl~nino)-phenyl] 0 ester Mop~ 79 C
4-~luoro-N-methylcarbanilic-acid [3-(ethylthiooarbonylamino)-phenyl]
e~ter Mopo 97-99C
3-Fluoro-N-metllylcarbanilic acid ~3~
t2-propynyloxycarbonylamino)-phenyl]
ester M.p~: 142-144C
N-Ethyl 3-~luorocarbanilic acid ~3-(2-propynyloxycarbonyl~nino)-phenyl]
ester M~po 148-150C
4-Fluoro-N-(2-phenylethyl)-carbanilic acid C3-tethylthiocarbonylamino)-phengl] ester Mop~ 117C
4-~luoro-N-(2-phenylethyl)-carbanilic acid [3-(1-methylethoxycarbonylamino~-phenylJ ester M.p.: 81-83C
N-Ethyl-4-fluorocarbanilic acid (3- 0 allyloxycarbonylaminophenyl) ester Mop~ 73-74 C
llZ~3~6~
Name of the compound Physical Constant , N-Ethyl-4-~luorocarbanilic acid ~3-(2-propynyloxycarbonylamino)-phenyl]
ester M.p.: 7g-80C
4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyloxycarbonylami~ophenyl) O
ester ~ M~p.: 81 C
~-~luoro-~-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylaminophenyl) 0 e~ter Mop~ 112-113 C
~-~thyl-2-fluorocarbænilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 106-107C
N-Ethyl-3,4-difluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 121-122C
3-~luoro-N-(2-phenylethyl)-carbanilic acid (3-etho~ycarbonylaminophenyl) O
ester M.p.: 115 C
3-~luoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)- O
phenyl~ ester , M~po ~1-93 C
3-~luoro-~-methylcarbanilic acid [3-(l-methylethoxycarbonylamino)-phenyl] e~ter M.p~: 74-76C
3-~luoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) cster Mop~ 78-80C
3-~luoro-N-e~îylcarbanilic acid (3-allylo~ycarbonylaminophenyl) ester Mop~ 101-10~C
4-Fluoro-~-methylcarbanilic acid (3- 20 allyloxycarbonylaminophenyl) ester nD : lo 5536 N-Ethyl-3-fluorocarbanilic acid ~3-(1-chloromethylethoxyc~rbonylamino)-phenyl] e~ter M~po 68-70C
N-Ethy1-3,4-di~luorocarbanilic acid (3-ethoxycarbonylaminophenyl) e~ter M.p.: 69-70C
N-~thyl-3,4-di~luorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl] O
ester M~po 130-132 C
1~28~!6~
Name o~ the eompound Phy~ical Con~tant 2-~luoro-~-(2-phenylethyl)-carbanilie aeid (3-methoxycarbonylaminophenyl) e~ter M~p.: 125-126C
2-~luoro-N-(2-phe~ylethyl)-carbanilie aeid (3-ethoxycarbonylaminophenyl) ester M.p.: 128-130C
2-Fluoro-N-(2-phenylethyl)-carbanilie aeid [~-(methylthiocarbonylamino)- .
phenyl~ e~ter M.p.: 148-149C
2-~luoro-N-(2-phenylethyl)-earbanilie acid l3-(ethylthiocarbonylamino)-phenyl] ester M~po 124C
2-Fluoro-N-(2-phenylethyl)-earbanilic aeid ~3~ methylethoxyearbonylamino)-phenyl] e~ter M.p.: 109-110C
3-~luoro-N-propylearbanilie aeîd (3-methoxyearbonyla~inophenyl) ester M.p.: 90-92C
3-Fluoro N-propvlcarbanilic aeid [3-(methylthioc~rbonylamino)-phenyl]
ester Mop~; 10~-lQ5C
3-Fluoro-N-propylearbanilie aeid (3-et.hoxyearbonylaminophenyl) e.C~ter M~p~. 1 n3_10sa N-~thyl-3-~luorocarbanil~o aeid [3-(l-methyl-2-proponyloxyearbonylamino)-~henyl] est.er M.p.: 100-101C
N-Ethyl-2-~luo~oc~rbanilie acid ~3-(l-methyl-2-propenyloxycarbollylamino)-phen~rl~ e~ter Mop~ los-lloa N-Ethyl-4-fluorocarbanilie aeid ~3-(1-methyl-2-propenylo~yearbonylamino)-phenyl] e~ter M.p.: 73-74C
N-Butyl-3-~luoroearbanilie aeid (3-me~hoxye~rbonylaminophenyl) ester M.p.: 79-80C
3-~luoro-~-methylearbanilie aeid [3-(2-methylpropoxyearbonylamino)-phenyl] e~ter M.p.: 94-95C
~128 6 ~
Name of the compound Phy6ical constant 4-Eluoro-~-(2-phenylethyl)-carballilic acid ~3~ methyl-2-propenylo~y- 20 carbonylamino~-phenyl~ ester nD : 1.5578 3-Fluoro-N-(2-phenylethyl)-carbanilic acid ~3-(1-methyl-2-propenyloxy- 20 carbonylamino)-phenyl] ester nD : 1.5632 3-Fluoro-N-methylcarbanilic acid ~3-(l-methyl-2-propenylo~ycarbonylamino)- 20 phenyl] ester nD : 1.5509 4-Fluoro-l~-methylcarbanilic acid ~3-methyl-2-propenyloxycarbonylamino)- 20 phenyl] ester nD : 1.5465 N-~ut~1-4-~luorocarbanilic acid C3-(l-methyl-2-propenylo~ycarbonylamino)- 20 phenyl] ester nD : lo 5298 4-~luoro-N-methylcarbanilic acid ~3-(2-methylpropoxycarbonylamino)- 20 phen~l] ester nD : 1.531~ ~
4-Eluoro-~-propylcarbanilic acid [3- t (l-metnyl-2-propenyloxycarbonyl~nino)-phenyl] ester Mop~ 75-76C
N-Ethyl-2-~l~orocarbanilic acid (3-ethoxycarbonylaminophenyl) ester M.p.: 151-153C
N-Ethyl-2-fluorocarb~nilic acid [3-(methylthiocarbonylamino)-phenyl~
ester M~p~o 150-162C
N-Eth~ 2-~luoroca~b~lilic acid [3-(ethylthiocarbonylamino)-ph~nyl]
ester M.p.: 146-147C
N~Ethyl~2-~luorocarbanili~ acid ~3-(l-methylethoxyoarbo~ylamino)-phenyl]
e~ter M.p.: 126-127C
N-~thyl-2-~luorocarb~lilic ac~d [3-(2-propynyloxycarbon~rlamino)-phenyl]
ester M.p.: 150C
Name of the compound Physical Con~tant 2-~luoro-N-(2-phen~lethyl)-carbanilic acid (~-allyloxycarbonylaminophenyl) e~ter M~p.: 72-73a 2-~luoro-~(2-phenylethyl)-carbanilic acid [~-(2-methylpropoxycarbonylamino)-phenyl] ester M.p.: 57-58C
4-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) e~ter nD : 1.5345 4-~luoro-I~-propylcarbanilic acid (3-etho~ycarbonylaminophenyl) ester Mop~ 64-66C
N-~utyl-4-fluorocarbani.lic acid (3-metho~ycarbonylaminophenyl) ester nD : lo 5322 N-~utyl-4-fluorocarbanilic acid (3- 20 etho~ycarbonylaminophenyl) ester nD : 1.5305 4-~luoro-N-butylcarbanilic acid [3-(l-methylethoxycarljonylamino)- O ' phenyl] e~ter ~I.p.: 81-83 C
4-~luoro-N-butylcarbanilic acid [3-(ethyithiocarbonyl~mino)-phenylJ O
e~ter Mop~ 73-75 C
N-~utyl-4-~luorocarbanilic acid 3-(2-propynyloxycarbonylamino)-phenylJ ~0 e~ter nD : 105439 4-Fluoro-I~propylcarbanilic acid ~3-(ethylthiocarbonylamino)-phenyl]
ester ;~.p.: 53-55C
4-~luoro-N-propylcarbanili.c acid [3-(2-propynyloxycarbonylamino)-phenyl] 20 eeter nD : 105461 N-~utyl-4-~luorocarbanilic acid C3-(methylthlocarbonylamino)-phenyl] 0 ester M~p.: 85-89 C
2-Fluoro-N-(2-phenylethyl)-carbanili.c acid C3-~2-propynyloxycarbonylamino)-phenyl] e~ter Mop~ 93-94C
1~21 In a series o~ te3ts carried out in a greenhouse, the compounds o~ the pre~ent invention listed in the Table below were each sprayed in accordance with the post-emergence method at a rate o~ application o~ 5 kg o*
active substance per hectare, emulsi~ied in 500 litres o~ water per hectare, on to Brassica and Solanum as the test plants. 3 week~ a~ter the treatment the results thereo~ were evaluated and expressed by a numerical ~cale extending from O to 4, the value O representing no action and the value 4 representing destrvction of the plant.
A~ will be seen frorn the Table, destruction of the plant~ wa~ achieved.
Cornpound of_ he inventlon Solanum Brassica 3-Fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 N-Ethyl-3-~luorocarbanilic acid (3-methoxycarbonylaminophen~l) ester 4 4 N-Ethyl-3-~luorocarbanilic acid C3-(methylthiocarbonylamino)~phellyl~
ester 4 4 4-~luoro-N-methylcarbanllic acid (3-metho~ycarbonylaminophenyl) ester 4 4 4-~luoro-N-methylcarbanilic acid ~3-(methylthiocarbonylamino)-phenyl]
e~ter 4 4 N-Ethyl-4-*luorocarbanilic acid ~3-(methylthiocarbonylamino)-phenylJ
e~ter 4 4 ~Z~3~6~ :
!
- 19 ~- j ~ompound o~ the invention Solanum Bra~sica 1.
N-Ethyl-4-fluorocarbanilie acid (3-metho~ycarbonylaminophenyl) e~ter 4 4 N-~thyl-4-fluoroearb~nilie acid (3-ethoxyearbonylaminophenyl) ester 4 N-~thyl-3-~luoroearbanilie aeid (3- -etho~yearbonylaminophenyl) e~ter 4 3-Fluoro-N-methylcarbanilie aeid (3-ethoxycarkonylaminophenyl) e~ter 4 4 3~1uoro-N-methylcarbanilie aeid [3-(methylthiocarbonylamino)-phenylJ
ester 4 4 3-~luoro-N-methylcarbanilic acid [3-(ethylthioearbonylamino)-phenyl]
e~ter 4 4 4-~luoro-N-methylearbanilie aeid (3-ethoxyearbonylaminophenyl) ester 4 4 4-~luoro-N-(2-phenylethyl)-earbanilie acid (3-methoxycarbonylam~nophenyl) e~ter 4 4 4-~luoro-N-(2-phenylethyl)-earbanilie aeid (3-ethoxyearbonylaminophenyl) ester 4 4 ~-Ethyl~3-~luorocarbanilic aeid [3-(l-me1;hylethoxycarbonylamino)-pllenyl]
~ter 4 4 N-Ethyl-4-fluoroear~anilie aeid [~
meth~letho~ye~rbonylamiIlo)-phenylJ
es~er 4 4 4-Fluoro-N-methylearbanilie aeid [3-(l-methylethoxyearbonyla~ino)-phenyl]
e~ter 4 4 N-~thyl-4-*luoroearbanilie aeid [3-(ethylthioearbonylamino)-phenyl3 e~ter 4 4 4-~luoro-N~methylcarbanilie aeid [3-(ethylthiocarbonyla~ino)-phenyl] ester 4 4 8~6~
Com~ound o~ the invention .Solanum ra~sica ~-Fluoro~N-methylcarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester 4 4 ~-Ethyl-3-fluorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl~
ester 4 4 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [~-(ethylthiocarbonylamino)-phenyl~ e~ter 4 4 4-~luoro-N-(2-phenylethyl)-carbanilic acid [~-(l-methylethoxycarbonylamino)-phenylJ ester 4 4 N-Ethyl 4-~luorocarbanilic acid (~-allylo~ycarbonylaminophenyl) e~ter 4 4 N-Ethyl-4-~luorocarbanilic acid ~3-(2-propynylo~ycarbonylamino)-phenyl]
ester 4 4 4-~luoro-N-(2-phenylethyl)-carbanillc acid (~-allylo2ycarbonylaminophenyl) ester 4 3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 3-~`luoro-N-methylcarbanilio acid C3-(l-methylethoxycarbonylamino)-phenyl]
ester 4 4 3-Fluoro-~-methylca~b~li.lic acid (3-allylo2ycarbonylaminophenyl) e~ter 4 4 3-~.Luoro-N-ethylcarbanilic acid (3-allylo~ycarbonylaminophenyl) e~ter 4 4 4-~luoro-N-methylcarbanilic acid (~-allyloxycarbonylaminophenyl) e~ter 4 4 N-~thyl-3-~luorooarbanil~c acid [3-(l-chloromethyletho2ycarbonylamino)-phenyl] e~ter 4 4 ~28~6~
Compound o~ the invention Solanum ~ra~ica N-~thyl-2-~luorocarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 N-Ethyl-3,4-dlfluorocarbanilic acid (3-metho~ycarbonylaminophenyl) ester 4 4 ~-Fluoro-N-~2-phenylethyl)-carbanillc acid (3-ethoxycarbonylaminophenyl) ester , . 4 4 3-Fluoro-N-(2-phenylethyl)-carbanilic acid [~-(ethylthiocarbonylamino)- -phenylJ ester 4 4 3-~luoro-N-(2-phenylethyl)-carbanilic acid C3-(ethylthiocarbonylamino)-phenyl] ester 4 N-~thyl-3,4-di~luorocarbanilic acid (3-ethoxycarbonylaminophenyl) e~ter 4 4 N-Ethy1-3,4-difluorocarbanilic acid ~3-(methylthiocarbonylamino)-phenyl]
ester 4 4 2-~luoro-N~(2-pheny].ethyl)-carbanilic acid (3-methoxyc'arbonylaminophenyl) e~ter 4 4 2-Fl~loro~N~(2-phellylethyl)-carbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4 2-Fluoro-N~(2-phenylethyl)-carbani~ic acid [3~(methylthiocarbon~ylam.inG)~
phenyl~ ester 4 4 2-Fluoro-N-(2-phonylethyl)-carbanili.c acid [~-(ethylthiocarbonylamino)-phenylJ e~ter 4 4 2-Fluoro-N-(2-phenyleth~yl)-carbanilic acid [~ methylethoxycarbonylamino)-phenylJ e~ter 4 4 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(2-propynyloxycarbonylamino)-phenylJ e~ter 4 4 - ~%8Q~l -- 2~ _ Compound o~ the invention Solanum _ras ica N-~thyl-2-~luorocarbanilic acid (3-etho}~ycarbon~laminophenyl) ester 4 4 N-Ethyl-2-~luorocarbanilic acid C~~
(methylthiocarbonylamino)-phenyl~
ester 4 4 N-~thyl-2-~luorocarbanilic acid [3-(ethylthiocarbonylamino)-phenyl]
ester 4 4 N--Ethyl-2-fluorocarbanilic acid [3-(l-methylethoxycarbonylamino)-phenyl] e~ter 4 4 N-~thyl-2-~luorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester 4 4 2-~luoro-N-(2-phenylethyl)-carba~ilic acid (3-allyloxycarbonylaminoI)henyl) ester 4 4 2-Fluoro-N-(2~phen~1ethyl)-carbanilic acid [3-(2-~ethylpropoxycarbonyla~ino)-phenylJ e~ter 4 4 ¢-~luoro-N-propylcarbanilic acid (3-~etho~ycarbonylaminophenyl) ester 4 4 4-~luoro-N-~)ropylcarbanllic acid (3-e'~io~ycarbonylaminopll~nyl) ester 4 4 ~utyl-4-~luorocarbanilic acid (3-.ethoxycarbonyl~minophcnyl) ester 4 4 N-~u~,yl-4-~luorocarba~ilic acid (3-e~hoxycarbonylaminophenyl) e~ter 4 4 4-~luoro-N-butylcarbanilic acid t3-tl-methyletlloxycarbonylamino)-phenyl]
ester 4 4 4-~luoro-N-~utylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl]
e~ter 4 4 Compound o~ the invention ~olanum ~ra~.ica N-~utyl-4-fluorocarbanilic acid [3-t2-propynyloxycarbonylamino)-phenyl]
ester 4 4 4-Fluoro-N-propylcarbanilic acid C3 (eth~lthiocarbonylamino)-phenyl~
ester 4 4 4-Fluoro-N-propylcarbanilic acid C3-(2-propynyloxycarbonylamino)-phenyl]
ester 4 4 N-~utyl-4-*luorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl]
es-ter 4 4 N-~thyl-3~ orocarbaMilic acld r3-(l-methyl-2-propenylo~ycarbonylamino)-phenyl] ester 4 4 N-~thyl-2-~luorocar~nilic acid ~3-(l-methyl-2-propenyloxycarbollylamin.o)-phenyl] ester 4 4 N-Ethyl-4-fluorocarbanilic acid [3-(1-methyl-2-propenylox~carbonylamino)-phenyl] ester 4 ¢
N-~utyl-3-~luorocarbanilic acid (3-metho~-ycarbon~rl~minoph~ryl) e~t~r 4 4 3-Fluoro-N-methylcarbanllic acid [3-(2-methylpropoxycarbonylamino)-phenyl]
e~ter 4 4 4-k'luoro-N-(2~phenylethyl)-carbanilic acid [3-(l~methyl-2-propenyloxy-carbonylamino)-l~he~yl] ester 4 4 3-Fluoro~N-(2-phenylethyl)-carbanilic acid C3-(1-methyl-2-propenyloxy-carbonylamillo)-~henyl] ester 4 4 3-~luoro-N-methylcarbanilic acid ~3-(l-methyl-2-propenyloxycarbonylamino)-phenyl] e~ter 4 4 llZB~61 om~und of the invention Solanum Br~s~ica 4-~luoro-N-methylcarbanilic acid r3-(l-methyl-2-propenyloxycarbonylamino) phenyl~ ester 4 4 N-~utyl-4-fluorocar~)~nilic acid [3-(l-methyl-2-propenylo~ycarbonylamino)-phenyl] ester 4 4 4-Fluoro-N-methylcarbanilic acid [3-(2-met~ylpropoxycarbonylamino)-phenyl]
ester 4 4 3-Fluoro-N-propylcarbanilic acid (3-metho~ycarbonylaminophenyl) ester 4 4 3-Ptluoro-N-prop~lcarbanilic acid ~3-(methylthiocarbonylamino)-phenyl]
ester 4 4 3-Fluoro-N-propylcarbanilic ac~d (~-etho~ycarbonyla~inophenyl) ester 4 4 Ex~a~_~
_., In a se~ie~ of tests carried out in a green~louse, the compound~ o~ the present invention listed in the Table below were each sprayed in accordance with the p~a-emergence method at a rate of application of 5 kg o~ active substance per hectare, emuL~i~ied in 600 litres o~ water per heotare, on to ~ and Solanum as the te~t plantæ. 3 weeks after the treatment the re~ulte thereo~ were evaluated and expressed b~y a n~nerical scale extending from 0 to 4, the value 0 representing no action and the value 4 repreæenting destruction of the plant.
A~ will be seen ~rom the ~'able, destruction o~ the te~t plants wa~ achleved.
1~2~6 -- 25 _ Compound of the invention Sol~um Bra,~ica 4-~luoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 N-~thyl-4-~luorocarbanilic acid (~-methoxycarbonylaminophenyl) ester 4 4 N-Ethyl-4-fluorocarb~nilic acid (3-ethoxycarbonylaminophenyl) ester ~ 4 4 4-Fluoro-N-methylcarbanilic acid (3-ethox~rcarbonylaminophenyl) ester 4 4 N-Ethyl-4-fluorocarbanilic acid [~-(l-meth~lethoxycarbonylamino)-phenyl] e~ter 4 4 Untreated xample 4 In a ~eries of tests carried out in a greenllouse, the plant~ listed in the Table below were treated a~ter their emergence ~Jith the agents li~ted usin~ in each case an application quantit~ o~ 1 ~g o~ active substance per hectare. ~or thi~ purpose, the agent~ were in each ca~e s~ayed unl~ormly over th~ ~lants in the ~o~m of an emulsion, u~ing 500 litres o~ water per hectare. In this ca~e, ~ ~eek~ ~ter the treatment thc compound~ o~
the present in~ent~on were ~ound to have high degree of oelectivity while having an excellent action against the weedeO The agents u~ed ~or comparison did not exhibit this ~electivity.
~ he re~ults obt~ined are expre~sed by a numerical scale extending from O to 10, the value O representing total destruction o~ the ~ t and the value 10 represen-ting no act~onO
llZ8~61 _ 26 --BOii~OO~ O O O O
S o o o o ~wo'd'I o o o o ~n~u ë~ o o o o ~1 ~--1 r l r~l aZ~I 'I ~ ~ , UO~O~ 0~ 1 0 ~nu-~uno~ ~ ~o .;
. a) P~ t~ ~ h ~ h . ~ ~ ~d C) o C~ C) cd C~ h O h ~ h C) b~
O rl~ r~ ~ r-~ a) ~1 a ~ ~r~ ~ rl ~ r~ ~
a> .q P~
.0 -~ ,Q _ ,o _~ ,o _~
~' h rl h ~I h O h O
~: Cd P~ ~d h .r O R C) ~ O~rl c)~,l O Q) O O O E3 0 E~
a) h ~:: h ~ h t~ h td ~ O ~ O '~ O r~ O
~ t o ~ ~0 q-lq~ rl q-~ O CH O
oI a I ~ I,o 1,O
~:1I ~ h ~ td h ~ h ,~:1 0 ~ o ~ .5~
~, ~ ~ +~ o ~ o ~3F~ ~ ~ h OI c~
~:; o .. : .
llZ1~6 ~o~ ou~ ~ ~ o~ ~o . .
eF.~ S ~ co ~ c~
~ ~ o ., 6n~ ~ c~ ~ o~
,o~ ,C ~ ' . , a~ ~ ,~ ,1 ~
UO~O~
~nu-p~rno~ ,1 1 1 , o ~3 h o o a~ o . . . ~ ~ ~ O
h a) ~ co:~ ~ co C~ o I ~ r~
.. C) ~ _~ ~ r~ ~OO r ~D
!` ~ -- r~ .
~ ~ ~ ~1 ~ O ~I) O
~ ~r1 ~ ~ C.) ~ o .Cl ~1 1~ C) O O ~ ~ O
,~ ho u~
P~ O ~` O ~¢ ~
~1 c~ rl h O~rl h O
rl O ~I) rl `_ oO '~
g ~ ~ g 1~ ." ,~ .,, oh ~1 t~ ~rl O h O.¢ :~ C) h S ~ --' ~ ~ I:t Q)~ S~ Q) ~a I ~ cd h ~ ~.o a) P. o~
r¢ CQh .¢ ~
o I~ o ~o o ~ o c~ I ~--r~ o s: s: h rl ~1 0 I rl a) h rl Q) r-l ~0 ~7 a) ~ o ,~
~jq ~ r¢ ~ O ~ ¢ ~ O
~ h I ~ ~ o ~ ~ o c~ a) ~i r¢ r-- ~ rC rC~ h 11 11 ~ ~ h ~ v h h ~ h h ~
b,O a) ~ o o ~ ~ O 1~ O C~t~ C) ~ P, rl .
N-Ethyl-4-~luorocarbanilic acid ~3-(methylthioca~bo~yla~ino)-phenyl] ester M.p.: 143-144C
N-Ethyl-4 ~luorocarbanilic acid (3-~ethoxycarbonyl~inophenyl) est~r M.p.: 117-118C
N-~thyl-4-~luorocarbanilic acid (3-ethoxycarbonylamillophenyl) ester M.p.: 76-7'la thyl-3-~luorocarbanilic acid (3-ethoxycarbonylaminophenyl) est~r M~po 122C
3-~luoro-N-methylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester Mopo 91-92C
~-~luoro-N-methylcarbanilic acid [3-(methylthiocarbonylamino)-phenyl~ ester ~I~po 116C
~-~luoro-N-methylcarbanilic acid ~3-(ethylthiocarbonylamino)-phenyl] ester M.p.: 124-125C
1~28~61 .
Name of the compound Phy~ical Constant 4-~luoro~N-methylcarbanilic acid (3~ 20 ethoxycarbonylaminophenyl) ester nD : 1.5472 4-~luoro-~-(2-phe~ylethyl)-carbanilic acid (3-methoxycarbonyl~ninophenyl) 0 ester M.p.: 137 C
4-Fluoro-N (2-phenylethyl)-carbanilic acid (3~ethoxycarbonylaminophenyl) O
es-ter M~p.: 103-104 C
N-~thyl-3-fluorocarbanilic acid t3-(1 ~ethylethoxycarbonylamino)-phenyl] ester M~po 98C
h~-Ethyl-4-fluorocarbanilic acid C~-(l-methylethoxycarbo~yl~nino) phenylJ
ester M~po 84-86C .
4-~luoro-~-methylcarbanilic acid C3-(l~methylethoxycarbonyla~ino)- O
phenyl] ester M.p.: 88 C
N-~thyl-4-fluorocarbanilic acid ~3-(ethylthiocarbonyl~nino)-phenyl] 0 ester Mop~ 79 C
4-~luoro-N-methylcarbanilic-acid [3-(ethylthiooarbonylamino)-phenyl]
e~ter Mopo 97-99C
3-Fluoro-N-metllylcarbanilic acid ~3~
t2-propynyloxycarbonylamino)-phenyl]
ester M.p~: 142-144C
N-Ethyl 3-~luorocarbanilic acid ~3-(2-propynyloxycarbonyl~nino)-phenyl]
ester M~po 148-150C
4-Fluoro-N-(2-phenylethyl)-carbanilic acid C3-tethylthiocarbonylamino)-phengl] ester Mop~ 117C
4-~luoro-N-(2-phenylethyl)-carbanilic acid [3-(1-methylethoxycarbonylamino~-phenylJ ester M.p.: 81-83C
N-Ethyl-4-fluorocarbanilic acid (3- 0 allyloxycarbonylaminophenyl) ester Mop~ 73-74 C
llZ~3~6~
Name of the compound Physical Constant , N-Ethyl-4-~luorocarbanilic acid ~3-(2-propynyloxycarbonylamino)-phenyl]
ester M.p.: 7g-80C
4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyloxycarbonylami~ophenyl) O
ester ~ M~p.: 81 C
~-~luoro-~-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylaminophenyl) 0 e~ter Mop~ 112-113 C
~-~thyl-2-fluorocarbænilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 106-107C
N-Ethyl-3,4-difluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester M.p.: 121-122C
3-~luoro-N-(2-phenylethyl)-carbanilic acid (3-etho~ycarbonylaminophenyl) O
ester M.p.: 115 C
3-~luoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)- O
phenyl~ ester , M~po ~1-93 C
3-~luoro-~-methylcarbanilic acid [3-(l-methylethoxycarbonylamino)-phenyl] e~ter M.p~: 74-76C
3-~luoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) cster Mop~ 78-80C
3-~luoro-N-e~îylcarbanilic acid (3-allylo~ycarbonylaminophenyl) ester Mop~ 101-10~C
4-Fluoro-~-methylcarbanilic acid (3- 20 allyloxycarbonylaminophenyl) ester nD : lo 5536 N-Ethyl-3-fluorocarbanilic acid ~3-(1-chloromethylethoxyc~rbonylamino)-phenyl] e~ter M~po 68-70C
N-Ethy1-3,4-di~luorocarbanilic acid (3-ethoxycarbonylaminophenyl) e~ter M.p.: 69-70C
N-~thyl-3,4-di~luorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl] O
ester M~po 130-132 C
1~28~!6~
Name o~ the eompound Phy~ical Con~tant 2-~luoro-~-(2-phenylethyl)-carbanilie aeid (3-methoxycarbonylaminophenyl) e~ter M~p.: 125-126C
2-~luoro-N-(2-phe~ylethyl)-carbanilie aeid (3-ethoxycarbonylaminophenyl) ester M.p.: 128-130C
2-Fluoro-N-(2-phenylethyl)-carbanilie aeid [~-(methylthiocarbonylamino)- .
phenyl~ e~ter M.p.: 148-149C
2-~luoro-N-(2-phenylethyl)-earbanilie acid l3-(ethylthiocarbonylamino)-phenyl] ester M~po 124C
2-Fluoro-N-(2-phenylethyl)-earbanilic aeid ~3~ methylethoxyearbonylamino)-phenyl] e~ter M.p.: 109-110C
3-~luoro-N-propylearbanilie aeîd (3-methoxyearbonyla~inophenyl) ester M.p.: 90-92C
3-Fluoro N-propvlcarbanilic aeid [3-(methylthioc~rbonylamino)-phenyl]
ester Mop~; 10~-lQ5C
3-Fluoro-N-propylearbanilie aeid (3-et.hoxyearbonylaminophenyl) e.C~ter M~p~. 1 n3_10sa N-~thyl-3-~luorocarbanil~o aeid [3-(l-methyl-2-proponyloxyearbonylamino)-~henyl] est.er M.p.: 100-101C
N-Ethyl-2-~luo~oc~rbanilie acid ~3-(l-methyl-2-propenyloxycarbollylamino)-phen~rl~ e~ter Mop~ los-lloa N-Ethyl-4-fluorocarbanilie aeid ~3-(1-methyl-2-propenylo~yearbonylamino)-phenyl] e~ter M.p.: 73-74C
N-Butyl-3-~luoroearbanilie aeid (3-me~hoxye~rbonylaminophenyl) ester M.p.: 79-80C
3-~luoro-~-methylearbanilie aeid [3-(2-methylpropoxyearbonylamino)-phenyl] e~ter M.p.: 94-95C
~128 6 ~
Name of the compound Phy6ical constant 4-Eluoro-~-(2-phenylethyl)-carballilic acid ~3~ methyl-2-propenylo~y- 20 carbonylamino~-phenyl~ ester nD : 1.5578 3-Fluoro-N-(2-phenylethyl)-carbanilic acid ~3-(1-methyl-2-propenyloxy- 20 carbonylamino)-phenyl] ester nD : 1.5632 3-Fluoro-N-methylcarbanilic acid ~3-(l-methyl-2-propenylo~ycarbonylamino)- 20 phenyl] ester nD : 1.5509 4-Fluoro-l~-methylcarbanilic acid ~3-methyl-2-propenyloxycarbonylamino)- 20 phenyl] ester nD : 1.5465 N-~ut~1-4-~luorocarbanilic acid C3-(l-methyl-2-propenylo~ycarbonylamino)- 20 phenyl] ester nD : lo 5298 4-~luoro-N-methylcarbanilic acid ~3-(2-methylpropoxycarbonylamino)- 20 phen~l] ester nD : 1.531~ ~
4-Eluoro-~-propylcarbanilic acid [3- t (l-metnyl-2-propenyloxycarbonyl~nino)-phenyl] ester Mop~ 75-76C
N-Ethyl-2-~l~orocarbanilic acid (3-ethoxycarbonylaminophenyl) ester M.p.: 151-153C
N-Ethyl-2-fluorocarb~nilic acid [3-(methylthiocarbonylamino)-phenyl~
ester M~p~o 150-162C
N-Eth~ 2-~luoroca~b~lilic acid [3-(ethylthiocarbonylamino)-ph~nyl]
ester M.p.: 146-147C
N~Ethyl~2-~luorocarbanili~ acid ~3-(l-methylethoxyoarbo~ylamino)-phenyl]
e~ter M.p.: 126-127C
N-~thyl-2-~luorocarb~lilic ac~d [3-(2-propynyloxycarbon~rlamino)-phenyl]
ester M.p.: 150C
Name of the compound Physical Con~tant 2-~luoro-N-(2-phen~lethyl)-carbanilic acid (~-allyloxycarbonylaminophenyl) e~ter M~p.: 72-73a 2-~luoro-~(2-phenylethyl)-carbanilic acid [~-(2-methylpropoxycarbonylamino)-phenyl] ester M.p.: 57-58C
4-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) e~ter nD : 1.5345 4-~luoro-I~-propylcarbanilic acid (3-etho~ycarbonylaminophenyl) ester Mop~ 64-66C
N-~utyl-4-fluorocarbani.lic acid (3-metho~ycarbonylaminophenyl) ester nD : lo 5322 N-~utyl-4-fluorocarbanilic acid (3- 20 etho~ycarbonylaminophenyl) ester nD : 1.5305 4-~luoro-N-butylcarbanilic acid [3-(l-methylethoxycarljonylamino)- O ' phenyl] e~ter ~I.p.: 81-83 C
4-~luoro-N-butylcarbanilic acid [3-(ethyithiocarbonyl~mino)-phenylJ O
e~ter Mop~ 73-75 C
N-~utyl-4-~luorocarbanilic acid 3-(2-propynyloxycarbonylamino)-phenylJ ~0 e~ter nD : 105439 4-Fluoro-I~propylcarbanilic acid ~3-(ethylthiocarbonylamino)-phenyl]
ester ;~.p.: 53-55C
4-~luoro-N-propylcarbanili.c acid [3-(2-propynyloxycarbonylamino)-phenyl] 20 eeter nD : 105461 N-~utyl-4-~luorocarbanilic acid C3-(methylthlocarbonylamino)-phenyl] 0 ester M~p.: 85-89 C
2-Fluoro-N-(2-phenylethyl)-carbanili.c acid C3-~2-propynyloxycarbonylamino)-phenyl] e~ter Mop~ 93-94C
1~21 In a series o~ te3ts carried out in a greenhouse, the compounds o~ the pre~ent invention listed in the Table below were each sprayed in accordance with the post-emergence method at a rate o~ application o~ 5 kg o*
active substance per hectare, emulsi~ied in 500 litres o~ water per hectare, on to Brassica and Solanum as the test plants. 3 week~ a~ter the treatment the results thereo~ were evaluated and expressed by a numerical ~cale extending from O to 4, the value O representing no action and the value 4 representing destrvction of the plant.
A~ will be seen frorn the Table, destruction of the plant~ wa~ achieved.
Cornpound of_ he inventlon Solanum Brassica 3-Fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 N-Ethyl-3-~luorocarbanilic acid (3-methoxycarbonylaminophen~l) ester 4 4 N-Ethyl-3-~luorocarbanilic acid C3-(methylthiocarbonylamino)~phellyl~
ester 4 4 4-~luoro-N-methylcarbanllic acid (3-metho~ycarbonylaminophenyl) ester 4 4 4-~luoro-N-methylcarbanilic acid ~3-(methylthiocarbonylamino)-phenyl]
e~ter 4 4 N-Ethyl-4-*luorocarbanilic acid ~3-(methylthiocarbonylamino)-phenylJ
e~ter 4 4 ~Z~3~6~ :
!
- 19 ~- j ~ompound o~ the invention Solanum Bra~sica 1.
N-Ethyl-4-fluorocarbanilie acid (3-metho~ycarbonylaminophenyl) e~ter 4 4 N-~thyl-4-fluoroearb~nilie acid (3-ethoxyearbonylaminophenyl) ester 4 N-~thyl-3-~luoroearbanilie aeid (3- -etho~yearbonylaminophenyl) e~ter 4 3-Fluoro-N-methylcarbanilie aeid (3-ethoxycarkonylaminophenyl) e~ter 4 4 3~1uoro-N-methylcarbanilie aeid [3-(methylthiocarbonylamino)-phenylJ
ester 4 4 3-~luoro-N-methylcarbanilic acid [3-(ethylthioearbonylamino)-phenyl]
e~ter 4 4 4-~luoro-N-methylearbanilie aeid (3-ethoxyearbonylaminophenyl) ester 4 4 4-~luoro-N-(2-phenylethyl)-earbanilie acid (3-methoxycarbonylam~nophenyl) e~ter 4 4 4-~luoro-N-(2-phenylethyl)-earbanilie aeid (3-ethoxyearbonylaminophenyl) ester 4 4 ~-Ethyl~3-~luorocarbanilic aeid [3-(l-me1;hylethoxycarbonylamino)-pllenyl]
~ter 4 4 N-Ethyl-4-fluoroear~anilie aeid [~
meth~letho~ye~rbonylamiIlo)-phenylJ
es~er 4 4 4-Fluoro-N-methylearbanilie aeid [3-(l-methylethoxyearbonyla~ino)-phenyl]
e~ter 4 4 N-~thyl-4-*luoroearbanilie aeid [3-(ethylthioearbonylamino)-phenyl3 e~ter 4 4 4-~luoro-N~methylcarbanilie aeid [3-(ethylthiocarbonyla~ino)-phenyl] ester 4 4 8~6~
Com~ound o~ the invention .Solanum ra~sica ~-Fluoro~N-methylcarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester 4 4 ~-Ethyl-3-fluorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl~
ester 4 4 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [~-(ethylthiocarbonylamino)-phenyl~ e~ter 4 4 4-~luoro-N-(2-phenylethyl)-carbanilic acid [~-(l-methylethoxycarbonylamino)-phenylJ ester 4 4 N-Ethyl 4-~luorocarbanilic acid (~-allylo~ycarbonylaminophenyl) e~ter 4 4 N-Ethyl-4-~luorocarbanilic acid ~3-(2-propynylo~ycarbonylamino)-phenyl]
ester 4 4 4-~luoro-N-(2-phenylethyl)-carbanillc acid (~-allylo2ycarbonylaminophenyl) ester 4 3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 3-~`luoro-N-methylcarbanilio acid C3-(l-methylethoxycarbonylamino)-phenyl]
ester 4 4 3-Fluoro-~-methylca~b~li.lic acid (3-allylo2ycarbonylaminophenyl) e~ter 4 4 3-~.Luoro-N-ethylcarbanilic acid (3-allylo~ycarbonylaminophenyl) e~ter 4 4 4-~luoro-N-methylcarbanilic acid (~-allyloxycarbonylaminophenyl) e~ter 4 4 N-~thyl-3-~luorooarbanil~c acid [3-(l-chloromethyletho2ycarbonylamino)-phenyl] e~ter 4 4 ~28~6~
Compound o~ the invention Solanum ~ra~ica N-~thyl-2-~luorocarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 N-Ethyl-3,4-dlfluorocarbanilic acid (3-metho~ycarbonylaminophenyl) ester 4 4 ~-Fluoro-N-~2-phenylethyl)-carbanillc acid (3-ethoxycarbonylaminophenyl) ester , . 4 4 3-Fluoro-N-(2-phenylethyl)-carbanilic acid [~-(ethylthiocarbonylamino)- -phenylJ ester 4 4 3-~luoro-N-(2-phenylethyl)-carbanilic acid C3-(ethylthiocarbonylamino)-phenyl] ester 4 N-~thyl-3,4-di~luorocarbanilic acid (3-ethoxycarbonylaminophenyl) e~ter 4 4 N-Ethy1-3,4-difluorocarbanilic acid ~3-(methylthiocarbonylamino)-phenyl]
ester 4 4 2-~luoro-N~(2-pheny].ethyl)-carbanilic acid (3-methoxyc'arbonylaminophenyl) e~ter 4 4 2-Fl~loro~N~(2-phellylethyl)-carbanilic acid (3-ethoxycarbonylaminophenyl) ester 4 4 2-Fluoro-N~(2-phenylethyl)-carbani~ic acid [3~(methylthiocarbon~ylam.inG)~
phenyl~ ester 4 4 2-Fluoro-N-(2-phonylethyl)-carbanili.c acid [~-(ethylthiocarbonylamino)-phenylJ e~ter 4 4 2-Fluoro-N-(2-phenyleth~yl)-carbanilic acid [~ methylethoxycarbonylamino)-phenylJ e~ter 4 4 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(2-propynyloxycarbonylamino)-phenylJ e~ter 4 4 - ~%8Q~l -- 2~ _ Compound o~ the invention Solanum _ras ica N-~thyl-2-~luorocarbanilic acid (3-etho}~ycarbon~laminophenyl) ester 4 4 N-Ethyl-2-~luorocarbanilic acid C~~
(methylthiocarbonylamino)-phenyl~
ester 4 4 N-~thyl-2-~luorocarbanilic acid [3-(ethylthiocarbonylamino)-phenyl]
ester 4 4 N--Ethyl-2-fluorocarbanilic acid [3-(l-methylethoxycarbonylamino)-phenyl] e~ter 4 4 N-~thyl-2-~luorocarbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester 4 4 2-~luoro-N-(2-phenylethyl)-carba~ilic acid (3-allyloxycarbonylaminoI)henyl) ester 4 4 2-Fluoro-N-(2~phen~1ethyl)-carbanilic acid [3-(2-~ethylpropoxycarbonyla~ino)-phenylJ e~ter 4 4 ¢-~luoro-N-propylcarbanilic acid (3-~etho~ycarbonylaminophenyl) ester 4 4 4-~luoro-N-~)ropylcarbanllic acid (3-e'~io~ycarbonylaminopll~nyl) ester 4 4 ~utyl-4-~luorocarbanilic acid (3-.ethoxycarbonyl~minophcnyl) ester 4 4 N-~u~,yl-4-~luorocarba~ilic acid (3-e~hoxycarbonylaminophenyl) e~ter 4 4 4-~luoro-N-butylcarbanilic acid t3-tl-methyletlloxycarbonylamino)-phenyl]
ester 4 4 4-~luoro-N-~utylcarbanilic acid [3-(ethylthiocarbonylamino)-phenyl]
e~ter 4 4 Compound o~ the invention ~olanum ~ra~.ica N-~utyl-4-fluorocarbanilic acid [3-t2-propynyloxycarbonylamino)-phenyl]
ester 4 4 4-Fluoro-N-propylcarbanilic acid C3 (eth~lthiocarbonylamino)-phenyl~
ester 4 4 4-Fluoro-N-propylcarbanilic acid C3-(2-propynyloxycarbonylamino)-phenyl]
ester 4 4 N-~utyl-4-*luorocarbanilic acid [3-(methylthiocarbonylamino)-phenyl]
es-ter 4 4 N-~thyl-3~ orocarbaMilic acld r3-(l-methyl-2-propenylo~ycarbonylamino)-phenyl] ester 4 4 N-~thyl-2-~luorocar~nilic acid ~3-(l-methyl-2-propenyloxycarbollylamin.o)-phenyl] ester 4 4 N-Ethyl-4-fluorocarbanilic acid [3-(1-methyl-2-propenylox~carbonylamino)-phenyl] ester 4 ¢
N-~utyl-3-~luorocarbanilic acid (3-metho~-ycarbon~rl~minoph~ryl) e~t~r 4 4 3-Fluoro-N-methylcarbanllic acid [3-(2-methylpropoxycarbonylamino)-phenyl]
e~ter 4 4 4-k'luoro-N-(2~phenylethyl)-carbanilic acid [3-(l~methyl-2-propenyloxy-carbonylamino)-l~he~yl] ester 4 4 3-Fluoro~N-(2-phenylethyl)-carbanilic acid C3-(1-methyl-2-propenyloxy-carbonylamillo)-~henyl] ester 4 4 3-~luoro-N-methylcarbanilic acid ~3-(l-methyl-2-propenyloxycarbonylamino)-phenyl] e~ter 4 4 llZB~61 om~und of the invention Solanum Br~s~ica 4-~luoro-N-methylcarbanilic acid r3-(l-methyl-2-propenyloxycarbonylamino) phenyl~ ester 4 4 N-~utyl-4-fluorocar~)~nilic acid [3-(l-methyl-2-propenylo~ycarbonylamino)-phenyl] ester 4 4 4-Fluoro-N-methylcarbanilic acid [3-(2-met~ylpropoxycarbonylamino)-phenyl]
ester 4 4 3-Fluoro-N-propylcarbanilic acid (3-metho~ycarbonylaminophenyl) ester 4 4 3-Ptluoro-N-prop~lcarbanilic acid ~3-(methylthiocarbonylamino)-phenyl]
ester 4 4 3-Fluoro-N-propylcarbanilic ac~d (~-etho~ycarbonyla~inophenyl) ester 4 4 Ex~a~_~
_., In a se~ie~ of tests carried out in a green~louse, the compound~ o~ the present invention listed in the Table below were each sprayed in accordance with the p~a-emergence method at a rate of application of 5 kg o~ active substance per hectare, emuL~i~ied in 600 litres o~ water per heotare, on to ~ and Solanum as the te~t plantæ. 3 weeks after the treatment the re~ulte thereo~ were evaluated and expressed b~y a n~nerical scale extending from 0 to 4, the value 0 representing no action and the value 4 repreæenting destruction of the plant.
A~ will be seen ~rom the ~'able, destruction o~ the te~t plants wa~ achleved.
1~2~6 -- 25 _ Compound of the invention Sol~um Bra,~ica 4-~luoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) ester 4 4 N-~thyl-4-~luorocarbanilic acid (~-methoxycarbonylaminophenyl) ester 4 4 N-Ethyl-4-fluorocarb~nilic acid (3-ethoxycarbonylaminophenyl) ester ~ 4 4 4-Fluoro-N-methylcarbanilic acid (3-ethox~rcarbonylaminophenyl) ester 4 4 N-Ethyl-4-fluorocarbanilic acid [~-(l-meth~lethoxycarbonylamino)-phenyl] e~ter 4 4 Untreated xample 4 In a ~eries of tests carried out in a greenllouse, the plant~ listed in the Table below were treated a~ter their emergence ~Jith the agents li~ted usin~ in each case an application quantit~ o~ 1 ~g o~ active substance per hectare. ~or thi~ purpose, the agent~ were in each ca~e s~ayed unl~ormly over th~ ~lants in the ~o~m of an emulsion, u~ing 500 litres o~ water per hectare. In this ca~e, ~ ~eek~ ~ter the treatment thc compound~ o~
the present in~ent~on were ~ound to have high degree of oelectivity while having an excellent action against the weedeO The agents u~ed ~or comparison did not exhibit this ~electivity.
~ he re~ults obt~ined are expre~sed by a numerical scale extending from O to 10, the value O representing total destruction o~ the ~ t and the value 10 represen-ting no act~onO
llZ8~61 _ 26 --BOii~OO~ O O O O
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Claims (115)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A diurethane of the general formula I
(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-alkynyl or halogeno-C2-C4-alkynyl group, Y represents a hydrogen or fluorine atom and X represents an oxygen or sulphur atom.
(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-alkynyl or halogeno-C2-C4-alkynyl 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 R1 repre-sents a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl or 2-phenylethyl group and R2 represents a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl, allyl, propargyl, chlorethyl, l-chlormethylethyl, 4-chlorobutynyl, l-methylpropynyl or 4-chlorobutenyl group.
3. N-Ethyl-3-fluorocarbanilic acid [3-(ethylthiocarbonyl-amino)-phenyl] ester.
4. 3-Fluoro-N-methylcarbanilic acid (3-methoxycarbonyl-aminophenyl) ester.
5. N-Ethyl-3-fluorocarbanilic acid (3-methoxycarbonyl-aminophenyl) ester.
6. N-Ethyl-3-fluorocarbanilic acid (3-(methylthiocarbonyl-aminophenyl)-phenyl] ester.
7. 4-Fluoro-N-methylcarbanilic acid (3-methoxycarbonyl-aminophenyl) ester.
8. 4-Fluoro-N-methylcarbanilic acid [3-(methylthiocar-bonylamino)-phenyl] ester.
9. N-Ethyl-4-fluorocarbanilic acid [3-(methylthiocar-bonylamino)-phenyl] ester.
10. N-Ethyl-4-fluorocarbanilic acid (3-methoxycarbonyl-aminophenyl) ester.
11. N-Ethyl-4-fluorocarbanilic acid (3-ethoxycarbonyl, aminophenyl) ester.
12. N-Ethyl-3-fluorocarbanilic acid (3-ethoxycarbonyl-aminophenyl) ester.
13. 3-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonyl-aminophenyl) ester.
14. 3-Fluoro-N-methylcarbanilic acid [3-(methylthio-carbonylamino)-phenyl] ester.
15. 3-Fluoro-N-methylcarbanilic acid [3-(ethylthiocar-bonylamino)-phenyl] ester.
16. 4-Fluoro-N-methylcarbanilic acid (3-ethoxycarbonyl-aminophenyl) ester.
17. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-methoxy-carbonylaminophenyl) ester.
18. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-ethoxy-carbonylaminophenyl) ester.
19. N-Ethyl-3-fluorocarbanilic acid [3-(1-methylethoxy-carbonylamino)-phenyl ester.
20, N-Ethyl-4-fluorocarbanilic acid [3-(l-methylethoxy-carbonylamino)-phenyl] ester.
21. 4-Fluoro-N-methylcarbanilic acid [3-(1-methylethoxy-carbonylamino)-phenyl] ester.
22. N-Ethyl-4-fluorocarbanilic acid [3-(ethylthiocar-bonylamino)-phenyl] ester.
23. 4-Fluoro-N-methylcarbanilic acid [3-(ethylthiocar-bonylamino)-phenyl] ester.
24. 3-Fluoro-N-methylcarbanilic acid [3-(2-propynyloxy-carbonylamino)-phenyl] ester.
25. N-Ethyl-3-fluorocarbanilic acid [3-(2-propynyloxy-carbonylamino)-phenyl] ester.
26. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
27. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(l-methylethoxycarbonylamino)-phenyl] ester.
28. N-Ethyl-4-fluorocarbanilic acid (3-allyloxycarbonyl-aminophenyl) ester.
29. N-Ethyl-4-fluorocarbanilic acid [3-(2-propynyloxy-carbonylamino)-phenyl] ester.
30. 4-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyl-oxycarbonylaminophenyl) ester.
31. 3-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-me-thoxycarbonylaminophenyl) ester.
32. N-Ethyl-2-fluorocarbanilic acid (3-methoxycarbonyl-aminophenyl) ester.
33. N-Ethyl-3,4-difluorocarbanilic acid (3-methoxycar-bonylaminophenyl) 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-methylethoxy-carbonylamino)-phenyl] ester.
37. 3-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonyl-aminophenyl) ester.
38. 3-Fluoro-N-ethylcarbanilic acid (3-allyloxycarbonyl-aminophenyl) ester.
39. 4-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonyl aminophenyl) ester.
40. N-Ethyl-3-fluorocarbanilic acid [3-(1-chloromethyl-ethoxycarbonylamino)-phenyl] ester.
41. N-Ethyl-3,4-difluorocarbanilic acid (3-ethoxycarbonyl-aminophenyl) ester.
42. N-Ethyl-3,4-difluorocarbanilic acid [3-(methylthio-carbonylamino)-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-Fluoro-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)-carbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl] ester.
49. 3-Fluoro-N-propylcarbanilic acid (3-methoxycarbonyl-aminophenyl) ester.
50. 3-Fluoro-N-propylcarbanilic acid [3-(methylthiocar-bonylamino)-phenyl] ester.
51. 3-Fluoro-N-propylcarbanilic acid (3-(ethoxycarbonyl-aminophenyl)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-methoxycarbonyl-aminophenyl) ester.
56. 3-Fluoro-N-methylcarbanilic acid [3-(2-methylpropoxy-carbonylamino)-phenyl] ester.
57. 4-Fluoro-N-(2-phenylethyl)-carbanilic 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-propenyloxycarbonylamino)-phenyl] ester.
60. 4-Fluoro-N-methylcarbanilic acid [3-(1-methyl-2-propenyloxycarbonylamino)-phenyl] ester.
61. N-Butyl-4-fluorocarbanilic acid [3-(1-methyl-2-propenyloxycarbonylamino)-phenyl] ester.
62. 4-Fluoro-N-methylcarbanilic acid [3-(2-methyl-propoxycarbonylamino)-phenyl] ester.
63. 4-Fluoro-N propylcarbanilic acid [3-(1-methyl-2-propenyloxycarbonylamino)-phenyl] ester.
64. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid [3-(2-methylpropoxycarbonylamino)-phenyl] ester.
65. 4-Fluoro-N-propylcarbanilic acid (3-methoxycarbonyl-aminophenyl) ester.
66. 4-Fluoro-N-propylcarbanilic acid (3-ethoxycarbonyl-aminophenyl) ester.
67. N-Butyl-4-fluorocarbanilic acid (3-methoxycarbonyl-aminophenyl) ester.
68. N-Butyl-4-fluorocarbanilic acid (3-ethoxycarbonyl-aminophenyl) ester.
69. 4-Fluoro-N-butylcarbanilic acid [3-(1-methylethoxy-carbonylamino)-phenyl] ester.
70. 4-Fluoro-N-butylcarbanilic acid [3-(ethylthiocar-bonylamino)-phenyl] ester.
71 N-Butyl-4-fluorocarbanilic acid [3-(2-propynyloxy-carbonylamino)-phenyl] ester.
72. 4-Fluoro-N-propylcarbanilic acid [3-ethylthiocar-bonylamino)-phenyl] ester.
73. 4-Fluoro-N-propylcarbanilic acid [3-(2-propynyloxy-carbonylamino)-phenyl] ester.
74. N-Butyl-4-fluorocarbanilic acid [3-(methylthiocar-bonylamino)-phenyl] ester.
75. N-Ethyl-2-fluorocarbanilic acid (3-ethoxycarbonyl-aminophenyl) ester.
76. N-Ethyl-2-fluorocarbanilic acid [3-(methylthiocar-bonylamino)-phenyl] ester.
77. N-Ethyl-2-fluorocarbanilic acid [3-ethylthiocar-bonylamino)-phenyl] ester.
78. N-Ethyl-2-fluorocarbanilic acid [3-(1-methylethoxy-carbonylamino)-phenyl] ester.
79. N-Ethyl-2-fluorocarbanilic acid [3-2-propynyloxy-carbonylamino)-phenyl] ester.
80. 2-Fluoro-N-(2-phenylethyl)-carbanilic acid (3-allyl-oxycarbonylaminophenyl) ester.
81. A process for the manufacture of 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, wherein (a) a compound of the gen-eral formula , in which R2 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 R1 and Y have the meanings given above, or (b) a com-pound 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 chloride 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 R1 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 Cl-CO-X-R2, in which R2 and X have the meanings given above.
82. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 1.
83. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 2, 3 or 4.
84. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 5, 6 or 7.
85. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 8, 9 or 10.
86. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 11, 12 or 13.
87. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 14, 15 or 16.
88. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 17, 18 or 19.
89. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 20, 21 or 22.
90. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 23, 24 or 25.
91. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 26, 27 or 28.
92. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 29, 30 or 31.
93. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 32, 33 or 34.
94. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 35, 36 or 37.
95. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 38, 39 or 40.
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 claimed in claim 41, 42 or 43.
97. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 44, 45 or 46.
98. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 47, 48 or 49.
99. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 50, 51 or 52.
100. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 53, 54 or 55.
101. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 56, 57 or 58.
102. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 59, 60 or 61.
103. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 62, 63 or 64.
104. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 65, 66 or 67.
105. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 68, 69 or 70.
106. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 71, 72 or 73.
107. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 74, 75 or 76.
108. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 77, 78 or 79.
109. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound claimed in claim 80.
110. A method as claimed in claim 82 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.
111. A method as claimed in claim 82 wherein two or more compounds of the general formula I are used for the treat-ment in a total amount within the range of from 1 to 5 kg per hectare.
112. 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 R1, R2, Y and X have the meanings given in claim 1.
113. A method as claimed in claim 112 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.
114. A method as claimed in claim 112 wherein two or more compounds of the general formula I are used for the treat-ment in a total amount within the range of from 1 to 5 kg per hectare.
115. A method as claimed in claim 112 wherein the crop is a cotton crop.
Applications Claiming Priority (2)
| 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 |
| DEP2901658.8 | 1979-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128061A true CA1128061A (en) | 1982-07-20 |
Family
ID=6060757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA343,600A Expired CA1128061A (en) | 1979-01-15 | 1980-01-14 | Herbicidally 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) | BG31495A3 (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 AT AT0013980A patent/AT365411B/en not_active IP Right Cessation
- 1980-01-11 PH PH23505A patent/PH15195A/en unknown
- 1980-01-11 MX MX808584U patent/MX5743E/en unknown
- 1980-01-11 DD DD80218424A patent/DD148709A5/en unknown
- 1980-01-11 SU SU802867755A patent/SU942587A3/en active
- 1980-01-12 EG EG21/80A patent/EG14116A/en active
- 1980-01-14 PL PL1980221361A patent/PL125248B1/en unknown
- 1980-01-14 HU HU8063A patent/HU181682B/en unknown
- 1980-01-14 SE SE8000278A patent/SE8000278L/en not_active Application Discontinuation
- 1980-01-14 MA MA18899A patent/MA18702A1/en unknown
- 1980-01-14 IL IL59126A patent/IL59126A/en unknown
- 1980-01-14 CA CA343,600A patent/CA1128061A/en not_active Expired
- 1980-01-14 BG BG046234A patent/BG31495A3/en unknown
- 1980-01-14 GR GR60957A patent/GR71679B/el unknown
- 1980-01-14 IT IT19194/80A patent/IT1130864B/en active
- 1980-01-14 RO RO8099869A patent/RO79454A/en unknown
- 1980-01-14 BG BG046235A patent/BG31465A3/en unknown
- 1980-01-14 PT PT70692A patent/PT70692A/en unknown
- 1980-01-15 ES ES487720A patent/ES487720A1/en not_active Expired
- 1980-01-15 DK DK16380A patent/DK16380A/en not_active Application Discontinuation
- 1980-01-15 FR FR8000793A patent/FR2446275A1/en active Granted
- 1980-01-15 CS CS80312A patent/CS212336B2/en unknown
- 1980-01-15 CH CH32280A patent/CH645343A5/en not_active IP Right Cessation
- 1980-01-15 AU AU54604/80A patent/AU532736B2/en not_active Ceased
- 1980-01-15 GB GB8001303A patent/GB2040939B/en not_active Expired
- 1980-01-15 AR AR279638A patent/AR224143A1/en active
- 1980-01-15 BE BE0/198971A patent/BE881152A/en not_active IP Right Cessation
- 1980-01-15 ZA ZA00800244A patent/ZA80244B/en unknown
- 1980-01-16 JP JP55002672A patent/JPS5823865B2/en not_active Expired
- 1980-09-10 BR BR8000161A patent/BR8000161A/en unknown
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| MKEX | Expiry |