NO128742B - - Google Patents

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Publication number
NO128742B
NO128742B NO00218/70A NO21870A NO128742B NO 128742 B NO128742 B NO 128742B NO 00218/70 A NO00218/70 A NO 00218/70A NO 21870 A NO21870 A NO 21870A NO 128742 B NO128742 B NO 128742B
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Norway
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acid
aliphatic
substituted
stabilizer
visible
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NO00218/70A
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Norwegian (no)
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H Freund
A Czyzewski
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Schering Ag
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
    • 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
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Description

Stabiliserte, flytende, herbicide Stabilized, liquid, herbicide

preparater inneholdende bis-carbamater. preparations containing bis-carbamates.

Foreliggende oppfinnelse angår stabilisering av flytende preparater inneholdende ra-bis-carbamater ved tilsetning av organiske syrer. The present invention relates to the stabilization of liquid preparations containing rabies-carbamates by the addition of organic acids.

Det er kjent at bis-carbamater av den generelle formel: It is known that bis-carbamates of the general formula:

hvor R^ er alkyl, cycloalkyl eller aryl som eventuelt er substituert med halogen og/eller alkyl og/eller trifluormethyl, R2 er hydrogen eller alkyl, eller R^ og R2 kan sammen med det nitrogenatom til hvilket de er bundet og eventuelt et ytterligere nitrogenatom og/eller oxygenatom danne en heterocyclisk ring, og R^ er alkyl, alkenyl eller alkynyl som eventuelt er uu-substituert med halogen, har gode herbicide egenskaper (norsk patentskrift nr. 115.194). where R^ is alkyl, cycloalkyl or aryl optionally substituted with halogen and/or alkyl and/or trifluoromethyl, R2 is hydrogen or alkyl, or R^ and R2 together with the nitrogen atom to which they are bound and optionally a further nitrogen atom and/or oxygen atom form a heterocyclic ring, and R 1 is alkyl, alkenyl or alkynyl which is optionally uu-substituted with halogen, has good herbicidal properties (Norwegian patent publication no. 115,194).

Av disse virkestoffer har særlig (3-methoxycarbonylamino-fenyl)-N-(3-methylfenyl)-carbamat slått igjennom i praksis. Of these active substances, particularly (3-methoxycarbonylamino-phenyl)-N-(3-methylphenyl)-carbamate has succeeded in practice.

Deres anvendelse skjer overveiende i form av flytende preparater som foruten virkestoffet inneholder minst ett organisk oppløs-ningsmiddel og minst ett overflateaktivt middel som vesentlige bestanddeler . Their use is predominantly in the form of liquid preparations which, in addition to the active ingredient, contain at least one organic solvent and at least one surface-active agent as essential components.

Slike flytende preparater har imidlertid den ulempe at de ikke er tilstrekkelig stabile og spaltes mer eller mindre sterkt ved lagring. Følgen er en endring av virkestoffkonsentrasjonen og dermed et virkningstap. However, such liquid preparations have the disadvantage that they are not sufficiently stable and decompose more or less strongly during storage. The consequence is a change in the active ingredient concentration and thus a loss of effectiveness.

Fra US patentskrift nr. 2.954-396 er der kjent en fremgangs-måte for stabilisering av N-substituerte alkylcarbamater mot hydro-lytisk spaltning. Som stabilisatorer foreslåes der eddiksyre, fosforsyre, saltsyre, ammoniumdihydrogenfosfat, ammoniumklorid, ferri-klorid og blandinger av disse forbindelser. From US patent no. 2,954-396, a method for stabilizing N-substituted alkylcarbamates against hydrolytic cleavage is known. Acetic acid, phosphoric acid, hydrochloric acid, ammonium dihydrogen phosphate, ammonium chloride, ferric chloride and mixtures of these compounds are suggested as stabilizers.

Disse stabilisatorer bevirker imidlertid, forsåvidt som de overhodet er oppløselig i de flytende m-bis-carbamatholdige oppløs-ninger, ingen eller utilstrekkelig stabilisering av de nevnte flytende preparater. These stabilizers, however, in so far as they are soluble at all in the liquid m-bis-carbamate-containing solutions, cause no or insufficient stabilization of the aforementioned liquid preparations.

Det har nu vist seg at flytende preparater inneholdende minst en forbindelse av den generelle formel: It has now been found that liquid preparations containing at least one compound of the general formula:

hvor R1 er alkyl med 1-8 carbonatomer, cycloalkyl med 5-8 carbonatomer eller en fenyl- eller nafthylrest som eventuelt er substituert med halogen og/eller lavere alkyl og/eller trifluormethyl, where R1 is alkyl with 1-8 carbon atoms, cycloalkyl with 5-8 carbon atoms or a phenyl or naphthyl residue which is optionally substituted with halogen and/or lower alkyl and/or trifluoromethyl,

og R_ er en lavere alkyl-, alkenyl- eller alkynylgruppe som eventuelt er endesubstituert tiied halogen, kan stabiliseres godt ved tilsetning av minst en organisk syre som er en alifatisk dicarboxylsyre, alifatisk hydroxycarboxylsyre, alifatisk hydroxy-tricarboxylsyre, nitro- og/eller klorsubstituert aromatisk monocarboxylsyre, aromatisk dicarboxylsyre, nitrosubstituert aromatisk dicarboxylsyre, alifatisk sulfonsyre eller aromatisk sulfonsyre som stabilisator. and R_ is a lower alkyl, alkenyl or alkynyl group which is optionally end-substituted with halogen, can be well stabilized by the addition of at least one organic acid which is an aliphatic dicarboxylic acid, aliphatic hydroxycarboxylic acid, aliphatic hydroxy-tricarboxylic acid, nitro- and/or chlorine-substituted aromatic monocarboxylic acid, aromatic dicarboxylic acid, nitro-substituted aromatic dicarboxylic acid, aliphatic sulphonic acid or aromatic sulphonic acid as stabilizer.

Disse tilsetninger oppviser i konsentrasjoner fra ca. 0,05 These additives show concentrations from approx. 0.05

til 5 vekt%, fortrinnsvis fra 0,25 til 1,0 vekt%, en god stabiliserende virkning. Virkningstapet ved lengre lagring av de flytende preparater forhindres herved vidtgående eller innskrenkes i det minste sterkt over lengre tid. to 5% by weight, preferably from 0.25 to 1.0% by weight, a good stabilizing effect. The loss of effectiveness during longer storage of the liquid preparations is thereby largely prevented or at least greatly reduced over a longer period of time.

Som stabiliserende tilsetninger er særlig egnet oxalsyre, malonsyre, maleinsyre, glycolsyre, melkesyre, citronsyre, fthalsyre, 5-nitro-isofthalsyre, 2-nitrobenzoesyre, 3,5-dinitrobenzoesyre, 4-klor-3-nitrobenzoesyre, 2-klor-3,5-dinitrobenzoesyre, methan-sulfonsyre, benzensulfonsyre, p-toluensulfonsyre og tetrapropylen-benzensulfonsyre. Oxalic acid, malonic acid, maleic acid, glycolic acid, lactic acid, citric acid, phthalic acid, 5-nitro-isophthalic acid, 2-nitrobenzoic acid, 3,5-dinitrobenzoic acid, 4-chloro-3-nitrobenzoic acid, 2-chloro-3, 5-dinitrobenzoic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid and tetrapropylene-benzenesulfonic acid.

De flytende preparater som skal stabiliseres, har den for plantevernmidler vanlige sammensetning. Som vesentlige bestanddeler kan spesielt nevnes: 1. Forbindelser av den ovenfor angitte generelle formel, særlig (3-methoxycarbonylaminofenyl)-N-(3-methylfenyl)-carbamat, som virkestoff. 2. Oppløsningsmiddel som aromatiske hydrocarboner, cycio-hexanon, isoforon, methylhexalin, dibutylfthalatj tetralin, dimethylsulfoxyd og dimethylformamid. 3. Overflateaktive stoffer, som polyethoxylerte aminer, alkoholer, syrer og alkylfenoler og salter av alkylerte benzen- og nafthalensulfonsyrer. The liquid preparations to be stabilized have the usual composition for plant protection products. As essential ingredients, the following can be mentioned in particular: 1. Compounds of the above-mentioned general formula, especially (3-methoxycarbonylaminophenyl)-N-(3-methylphenyl)-carbamate, as active ingredient. 2. Solvents such as aromatic hydrocarbons, cycio-hexanone, isophorone, methylhexalin, dibutyl phthalatj tetralin, dimethylsulfoxide and dimethylformamide. 3. Surfactants, such as polyethoxylated amines, alcohols, acids and alkylphenols and salts of alkylated benzene and naphthalene sulfonic acids.

Den kvantitative sammensetning av de flytende preparater er omtrent som følger: The quantitative composition of the liquid preparations is approximately as follows:

5 - 50%, fortrinnsvis 10 - 25 vekt% virkestoff. 5 - 50%, preferably 10 - 25% by weight active substance.

10 - 90%, fortrinnsvis 50 - 80 vekt% oppløsningsmiddel. 10 - 90%, preferably 50 - 80% by weight solvent.

2 - 40%, fortrinnsvis IO - 25 vekt% overflateaktivt middel. 2 - 40%, preferably 10 - 25% by weight surfactant.

Anvendelsen av de stabiliserte flytende preparater skjer som herbicider for bekjempelse av uønsket plantevekst. Herved utmerker herbicidene seg særlig til selektiv ugressbekjempelse i noen nytte-plant ekulturer, som sukkerroer og ris blant annet. Stabilisatorene som anvendes i preparatene ifølge oppfinnelsen, har herved ingen skadelige virkninger. Fremstillingen av de flytende preparater ifølge oppfinnelsen kan skje ved enkel blanding av de beskrevne bestanddeler. The stabilized liquid preparations are used as herbicides to combat unwanted plant growth. Hereby, the herbicides excel particularly for selective weed control in some useful plant crops, such as sugar beet and rice, among others. The stabilizers used in the preparations according to the invention have no harmful effects. The production of the liquid preparations according to the invention can take place by simple mixing of the described components.

Eksempel 1 Example 1

Der ble fremstilt flytende formuleringer av følgende sammensetning : Liquid formulations of the following composition were produced:

og oppbevart i glassflasker ved +70°C. Efter de i tabellen angitte tider ble prøver tatt og undersøkt ved tynnskiktskromatografi. and stored in glass bottles at +70°C. After the times indicated in the table, samples were taken and examined by thin-layer chromatography.

I tabellen betyr: In the table means:

+ ingen spaltning av virkestoffet er synlig ( < 10% spaltning) + no cleavage of the active substance is visible (< 10% cleavage)

- tydelig spaltning av virkestoffet er synlig - clear cleavage of the active ingredient is visible

Stabilisatorer ifølge US- patentskrift nr. 2. 954- 396 Stabilizers according to US Patent No. 2. 954-396

Fosforsyre + - Eddiksyre - - Phosphoric acid + - Acetic acid - -

Analoge resultater fåes også med f.eks. følgende forbindelser: (3-methoxycarbonylaminofenyl)-N-fenylcarbamat Analogous results are also obtained with e.g. the following compounds: (3-methoxycarbonylaminophenyl)-N-phenylcarbamate

(3-ethoxycarbonylaminof enyl)-N-(3-methylf enyl)-carbarnat (3-ethoxycarbonylaminofenyl)-N-(fenyl)-carbamat (3-methoxycarbonylaminof enyl)-N-(3-klorfenyl)-ca rbamat (3-ethoxycarbonylaminofenyl)-N-(3-klorfenyl)-ca rbamat (3-methoxycarbonylaminofenyl)-N-(n-butyl)-ca rbamat (3-methoxycarbonylam inof enyl)-N-(t-butyl)-ca rbamat (3-methoxycarbonylaminofenyl)-N-(sek-butyl)-carbamat (3-methoxycarbonylaminofenyl)-N-(pentyl-(2))-carbamat (3-methoxycarbonylaminofenyl)-N-(neopentyl)-carbamat (3-methoxycarbonylaminofenyl)-N-(3 15-dimethylfeny1)-carbamat (3-ethoxycarbonylaminophenyl)-N-(3-methylphenyl)-carbamate (3-ethoxycarbonylaminophenyl)-N-(phenyl)-carbamate (3-methoxycarbonylaminophenyl)-N-(3-chlorophenyl)-carbamate (3- ethoxycarbonylaminophenyl)-N-(3-chlorophenyl)-ca rbamate (3-methoxycarbonylaminophenyl)-N-(n-butyl)-ca rbamate (3-methoxycarbonylaminophenyl)-N-(t-butyl)-ca rbamate (3- methoxycarbonylaminophenyl)-N-(sec-butyl)-carbamate (3-methoxycarbonylaminophenyl)-N-(pentyl-(2)-carbamate (3-methoxycarbonylaminophenyl)-N-(neopentyl)-carbamate (3-methoxycarbonylaminophenyl)-N- (3 15-dimethylphenyl)-carbamate

Eksempel 2 Example 2

Til en flytende formulering av følgende sammensetning: For a liquid formulation of the following composition:

ble tilsatt stigende mengder stabilisator, og de således erholdte preparater ble lagret ved de angitte temperaturer. Efter de i increasing amounts of stabilizer were added, and the preparations thus obtained were stored at the indicated temperatures. After those in

tabellen angitte tider ble prøver tatt, og graden av virkestoffspaltning ble bestemt kvantitativt. at the times indicated in the table, samples were taken, and the degree of active substance decomposition was determined quantitatively.

%-angivelsene i tabellen angir spaltningsgraden. The % values in the table indicate the degree of cleavage.

Eksempel 3 Example 3

Til et flytende preparat av følgende sammensetning: For a liquid preparation of the following composition:

16,7 vekt% (3-ethoxycarbonylaminofenyl)-N-(3-methylfenyl)-ca rbamat 16.7% by weight of (3-ethoxycarbonylaminophenyl)-N-(3-methylphenyl)-ca rbamate

ble de i det følgende angitte stabilisatorer tilsatt og de således erholdte formuleringer lagret ved 55 og 70°C. Efter de angitte tider ble prøver tatt og undersøkt ved tynnskiktskromatografi. the following stabilizers were added and the formulations thus obtained were stored at 55 and 70°C. After the indicated times, samples were taken and examined by thin-layer chromatography.

I tabellen betyr In the table means

+ ingen virkestoffspaltning synlig + no active substance decomposition visible

(+) svak virkstoffspaltning synlig (+) weak active substance cleavage visible

sterk virkstoffspaltning synlig strong active substance cleavage visible

Eksempel 4 Example 4

Til et flytende preparat av sammensetning: For a liquid preparation of composition:

ble de i den følgende tabell angitte stabilisatorer tilsatt, og de således erholdte formuleringer ble lagret ved 55 og 70°C. Efter de angitte tider ble prøver tatt og undersøkt ved tynnskiktskromato-graf i. the stabilizers specified in the following table were added, and the formulations thus obtained were stored at 55 and 70°C. After the stated times, samples were taken and examined by thin-layer chromatography.

I tabellen betyr In the table means

+ ingen virkestoffspaltning synlig + no active substance decomposition visible

(+) svak virkestoffspaltning synlig (+) weak active ingredient cleavage visible

- sterk virkestoffspaltning synlig - strong active substance cleavage visible

Eksempel 5 Example 5

Til en flytende formulering av følgende sammenseting: For a liquid formulation of the following composition:

ble tilsatt malonsyre i stigende mengder, og de således erholdte formuleringer ble lagret ved 20°, 55° og 70°C. Efter de i tabellen angitte tider ble prøver tatt og undersøkt ved tynnskiktskromato-graf i. malonic acid was added in increasing amounts, and the formulations thus obtained were stored at 20°, 55° and 70°C. After the times indicated in the table, samples were taken and examined by thin-layer chromatography.

I tahellen betyr In tahellen means

+ ingen spaltning av virkestoffet synlig + no visible splitting of the active substance

(+) liten spaltning av virkestoffet synlig sterk spaltning av virkestoffet synlig (+) slight cleavage of the active substance visible strong cleavage of the active substance visible

Eksempel 6 Example 6

Til et flytende preparat av følgende sammensetning: For a liquid preparation of the following composition:

ble den i den følgende tabell angitte stabilisator tilsatt, og de således erholdte preparater ble lagret ved 55 - 70°C i sammenligning med preparatet uten stabilisator. Efter de angitte tider ble prøver tatt og undersøkt ved tynnskiktskromatografi. the stabilizer indicated in the following table was added, and the preparations thus obtained were stored at 55 - 70°C in comparison with the preparation without stabilizer. After the indicated times, samples were taken and examined by thin-layer chromatography.

I tabellen betyr In the table means

+ ingen spaltning av virkestoffet synlig + no visible splitting of the active ingredient

(+) liten spaltning av virkestoffet synlig (+) slight cleavage of the active ingredient visible

sterk spaltning av virkestoffet synlig strong cleavage of the active substance visible

Eksempel 7 Example 7

Til et flytende preparat av sammensetningen: For a liquid preparation of the composition:

ble tilsatt 1 vekt% malonsyre, og det således erholdte stabiliserte preparat ble lagret i sammenligning med ikke-stabiliseft preparat ved 70°C. Efter de i tabellen angitte tider ble der tatt prøver som ble undersøkt ved tynnskiktskromatografi. 1% by weight of malonic acid was added, and the thus obtained stabilized preparation was stored in comparison with non-stabilised preparation at 70°C. After the times indicated in the table, samples were taken which were examined by thin-layer chromatography.

I tabellen betyr In the table means

+ ingen spaltning av virkestoffet synlig + no visible splitting of the active ingredient

- sterk spaltning av virkestoffet synlig - strong cleavage of the active ingredient visible

Eksempel 8 Example 8

I et emulsjonskonsentrat av følgende sammensetning: ble stigende mengder oppløsningsmiddel erstattet med citronsyre som stabilisator. De således erholdte preparater ble lagret i 4 måneder ved 70°C og derefter kvantitativt undersøkt på graden av virkestoffspaltning. In an emulsion concentrate of the following composition: increasing amounts of solvent were replaced with citric acid as stabilizer. The preparations thus obtained were stored for 4 months at 70°C and then quantitatively examined for the degree of active substance decomposition.

Citronsyre er den foretrukne stabilisator da den, som det frem-går av det ovenstående, er virksom i meget lav konsentrasjon. Citric acid is the preferred stabilizer as, as can be seen from the above, it is effective in a very low concentration.

Claims (2)

1. Stabiliserte, flytende, herbicide preparater inneholdende som vesentlige bestanddeler minst en forbindelse med den generelle formel: hvor er alkyl med 1-8 carbonatomer, cycloalkyl med 5 - 8 carbonatomer eller en fenyl- eller nafthylrest som eventuelt er substituert med halogen og/eller lavere alkyl og/eller trifluormethyl, og Rg er en lavere alkyl-, alkenyl- eller alkynylgruppe som eventuelt er endesubstituert med halogen, minst ett organisk oppløsningsmiddel og minst ett overflateaktivt stoff, karakterisert ved at det inneholder minst en organisk syre som er en alifatisk dicarboxylsyre, alifatisk hydroxycarboxylsyre, alifatisk hydroxy-tricarboxylsyre, nitro- og/eller klorsubstituert aromatisk monocarboxylsyre, aromatisk dicarboxylsyre, nitrosubstituert aromatisk dicarboxylsyre, alifatisk sulfonsyre eller aromatisk sulfonsyre som stabilisator.1. Stabilized, liquid, herbicidal preparations containing as essential constituents at least one compound with the general formula: where is alkyl with 1-8 carbon atoms, cycloalkyl with 5-8 carbon atoms or a phenyl or naphthyl residue which is optionally substituted with halogen and/or lower alkyl and/or trifluoromethyl, and Rg is a lower alkyl, alkenyl or alkynyl group which is optionally end-substituted with halogen, at least one organic solvent and at least one surfactant, characterized in that it contains at least one organic acid which is an aliphatic dicarboxylic acid, aliphatic hydroxycarboxylic acid, aliphatic hydroxy-tricarboxylic acid, nitro- and/or chlorine-substituted aromatic monocarboxylic acid, aromatic dicarboxylic acid, nitro-substituted aromatic dicarboxylic acid, aliphatic sulfonic acid or aromatic sulfonic acid as a stabilizer. 2. Preparat ifølge krav 1, karakterisert ved at det inneholder citronsyre som stabilisator.2. Preparation according to claim 1, characterized in that it contains citric acid as a stabilizer.
NO00218/70A 1969-01-22 1970-01-21 NO128742B (en)

Applications Claiming Priority (1)

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DE1903817A DE1903817C3 (en) 1969-01-22 1969-01-22 Stabilized liquid herbicide concentrates based on carbamate

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YU45662B (en) * 1983-09-20 1992-07-20 Berol Nobel (Suisse) S.A. PROCEDURE FOR OBTAINING FENMEDIFAM OR DESMEDIFAM
CZ156191A3 (en) * 1984-02-29 1995-10-18 Schering Ag Stabilized liquid herbicidal agent and method of controlling weed
US5246912A (en) * 1984-02-29 1993-09-21 Berol Nobel (Suisse) S.A. Herbicidal compositions of phenmedipham and desmedipham
JPS61176502A (en) * 1985-01-30 1986-08-08 Yamaide Kosan Kk Thermally molded article for insecticidal and fungicidal use
DE3645248C2 (en) * 1985-02-08 1996-01-25 Nippon Catalytic Chem Ind Stabilised alkoxylate of organic hydroxy cpd.
US4737314A (en) 1985-02-08 1988-04-12 Nippon Shokubai Kagaku Kogyo Co., Ltd. Stabilized alkylene oxide adduct containing lactic acid or a lactate
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US2954396A (en) * 1958-05-16 1960-09-27 Pure Oil Co Stabilization of carbamate esters
US2954397A (en) * 1958-09-25 1960-09-27 Pure Oil Co Stabilization of carbamate esters and extraction of aromatic hydrocarbons therewith
CH457400A (en) * 1965-06-25 1968-06-15 Agripat Sa Process for the preparation of new carbamic acid esters and their use for controlling pests
FR1523596A (en) * 1966-05-06 1968-05-03 Du Pont Stabilized compositions of esters of 2-alkoxy-carbonylamino-benzimidazolecarboxylic acids
US3553328A (en) * 1967-02-28 1971-01-05 Chevron Res Stable carbamate insecticide granules

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FR2028876A1 (en) 1970-10-16
MY7400096A (en) 1974-12-31
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IL33723A (en) 1973-08-29
NL163097B (en) 1980-03-17
BG17438A3 (en) 1973-11-10
FI51648B (en) 1976-11-30
IL33723A0 (en) 1970-06-17
LU60143A1 (en) 1970-03-06
DE1903817A1 (en) 1970-08-27
IE34001B1 (en) 1975-01-08
NL163097C (en) 1980-08-15
SE371081B (en) 1974-11-11
OA03207A (en) 1970-12-15
FI51648C (en) 1977-03-10
CS158259B2 (en) 1974-10-15
DE1903817C3 (en) 1981-06-25
RO56647A (en) 1974-07-01
BE744774A (en) 1970-07-22
AT298146B (en) 1972-04-25
IE34001L (en) 1970-07-22
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DE1903817B2 (en) 1980-08-21
CH514985A (en) 1971-11-15

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