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
- Authority
- NO
- Norway
- Prior art keywords
- acid
- aliphatic
- substituted
- stabilizer
- visible
- Prior art date
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- 238000002360 preparation method Methods 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 17
- 239000003381 stabilizer Substances 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- -1 aromatic monocarboxylic acid Chemical class 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 239000000470 constituent Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 14
- 238000003776 cleavage reaction Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 230000007017 scission Effects 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000012669 liquid formulation Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ADTKEYLCJYYHHH-UHFFFAOYSA-N 2-chloro-3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1Cl ADTKEYLCJYYHHH-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 description 1
- DFXQXFGFOLXAPO-UHFFFAOYSA-N 96-99-1 Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DFXQXFGFOLXAPO-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 206010037742 Rabies Diseases 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- PVLUURYNFHFRQR-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] n-butan-2-ylcarbamate Chemical compound CCC(C)NC(=O)OC1=CC=CC(NC(=O)OC)=C1 PVLUURYNFHFRQR-UHFFFAOYSA-N 0.000 description 1
- MLNOEQVEPIITAK-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=CC=CC=2)=C1 MLNOEQVEPIITAK-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FODHIQQNHOPUKH-UHFFFAOYSA-N tetrapropylene-benzenesulfonic acid Chemical compound CC1CC11C2=C3S(=O)(=O)OC(C)CC3=C3C(C)CC3=C2C1C FODHIQQNHOPUKH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- A01N25/22—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
- A01N25/02—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
- A01N25/30—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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Description
Stabiliserte, flytende, herbicide
preparater inneholdende bis-carbamater.
Foreliggende oppfinnelse angår stabilisering av flytende preparater inneholdende ra-bis-carbamater ved tilsetning av organiske syrer.
Det er kjent at bis-carbamater av den generelle formel:
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).
Av disse virkestoffer har særlig (3-methoxycarbonylamino-fenyl)-N-(3-methylfenyl)-carbamat slått igjennom i praksis.
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 .
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.
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.
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.
Det har nu vist seg at flytende preparater inneholdende minst en forbindelse av den generelle formel:
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,
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.
Disse tilsetninger oppviser i konsentrasjoner fra ca. 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.
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.
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.
Den kvantitative sammensetning av de flytende preparater er omtrent som følger:
5 - 50%, fortrinnsvis 10 - 25 vekt% virkestoff.
10 - 90%, fortrinnsvis 50 - 80 vekt% oppløsningsmiddel.
2 - 40%, fortrinnsvis IO - 25 vekt% overflateaktivt middel.
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.
Eksempel 1
Der ble fremstilt flytende formuleringer av følgende sammensetning :
og oppbevart i glassflasker ved +70°C. Efter de i tabellen angitte tider ble prøver tatt og undersøkt ved tynnskiktskromatografi.
I tabellen betyr:
+ ingen spaltning av virkestoffet er synlig ( < 10% spaltning)
- tydelig spaltning av virkestoffet er synlig
Stabilisatorer ifølge US- patentskrift nr. 2. 954- 396
Fosforsyre + - Eddiksyre - -
Analoge resultater fåes også med f.eks. følgende forbindelser: (3-methoxycarbonylaminofenyl)-N-fenylcarbamat
(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
Eksempel 2
Til en flytende formulering av følgende sammensetning:
ble tilsatt stigende mengder stabilisator, og de således erholdte preparater ble lagret ved de angitte temperaturer. Efter de i
tabellen angitte tider ble prøver tatt, og graden av virkestoffspaltning ble bestemt kvantitativt.
%-angivelsene i tabellen angir spaltningsgraden.
Eksempel 3
Til et flytende preparat av følgende sammensetning:
16,7 vekt% (3-ethoxycarbonylaminofenyl)-N-(3-methylfenyl)-ca rbamat
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.
I tabellen betyr
+ ingen virkestoffspaltning synlig
(+) svak virkstoffspaltning synlig
sterk virkstoffspaltning synlig
Eksempel 4
Til et flytende preparat av sammensetning:
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.
I tabellen betyr
+ ingen virkestoffspaltning synlig
(+) svak virkestoffspaltning synlig
- sterk virkestoffspaltning synlig
Eksempel 5
Til en flytende formulering av følgende sammenseting:
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.
I tahellen betyr
+ ingen spaltning av virkestoffet synlig
(+) liten spaltning av virkestoffet synlig sterk spaltning av virkestoffet synlig
Eksempel 6
Til et flytende preparat av følgende sammensetning:
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.
I tabellen betyr
+ ingen spaltning av virkestoffet synlig
(+) liten spaltning av virkestoffet synlig
sterk spaltning av virkestoffet synlig
Eksempel 7
Til et flytende preparat av sammensetningen:
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.
I tabellen betyr
+ ingen spaltning av virkestoffet synlig
- sterk spaltning av virkestoffet synlig
Eksempel 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.
Citronsyre er den foretrukne stabilisator da den, som det frem-går av det ovenstående, er virksom i meget lav konsentrasjon.
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.
2. Preparat ifølge krav 1, karakterisert ved at det inneholder citronsyre som stabilisator.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1903817A DE1903817C3 (de) | 1969-01-22 | 1969-01-22 | Stabilisierte flüssige Herbizidkonzentrate auf Carbamatbasis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128742B true NO128742B (no) | 1974-01-07 |
Family
ID=5723428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00218/70A NO128742B (no) | 1969-01-22 | 1970-01-21 |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS491850B1 (no) |
| AT (1) | AT298146B (no) |
| BE (1) | BE744774A (no) |
| BG (1) | BG17438A3 (no) |
| CH (1) | CH514985A (no) |
| CS (1) | CS158259B2 (no) |
| CY (1) | CY740A (no) |
| DE (1) | DE1903817C3 (no) |
| DK (1) | DK124656B (no) |
| ES (1) | ES374739A1 (no) |
| FI (1) | FI51648C (no) |
| FR (1) | FR2028876A1 (no) |
| GB (1) | GB1300094A (no) |
| IE (1) | IE34001B1 (no) |
| IL (1) | IL33723A (no) |
| LU (1) | LU60143A1 (no) |
| MY (1) | MY7400096A (no) |
| NL (1) | NL163097C (no) |
| NO (1) | NO128742B (no) |
| OA (1) | OA03207A (no) |
| PH (1) | PH9385A (no) |
| RO (1) | RO56647A (no) |
| SE (1) | SE371081B (no) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8604495A1 (es) * | 1983-09-20 | 1986-02-01 | Koege Kemisk Vaerk | Un procedimiento para preparar fenil-carbamatos sustituidos |
| SK278523B6 (en) * | 1984-02-29 | 1997-08-06 | Erik Nielsen | A stabilised liquid herbicidal agent and method for killing weed plants |
| US5246912A (en) * | 1984-02-29 | 1993-09-21 | Berol Nobel (Suisse) S.A. | Herbicidal compositions of phenmedipham and desmedipham |
| JPS61176502A (ja) * | 1985-01-30 | 1986-08-08 | Yamaide Kosan Kk | 防虫、防菌用加熱成形物 |
| US4737314A (en) | 1985-02-08 | 1988-04-12 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Stabilized alkylene oxide adduct containing lactic acid or a lactate |
| DE3645248C2 (de) * | 1985-02-08 | 1996-01-25 | Nippon Catalytic Chem Ind | Flüssige Detergensmischung |
| DK191386D0 (da) * | 1986-04-24 | 1986-04-24 | Koege Kemisk Vaerk | Emulgatorsystem |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (de) * | 1965-06-25 | 1968-06-15 | Agripat Sa | Verfahren zur Herstellung neuer Carbaminsäureester und ihre Verwendung zur Bekämpfung von Schädlingen |
| FR1523596A (fr) * | 1966-05-06 | 1968-05-03 | Du Pont | Compositions stabilisées d'esters des acides 2-alkoxy-carbonylamino-benzimidazolecarboxyliques |
| US3553328A (en) * | 1967-02-28 | 1971-01-05 | Chevron Res | Stable carbamate insecticide granules |
-
1969
- 1969-01-22 DE DE1903817A patent/DE1903817C3/de not_active Expired
- 1969-12-09 DK DK650069AA patent/DK124656B/da not_active IP Right Cessation
- 1969-12-17 FI FI693662A patent/FI51648C/fi active
- 1969-12-18 CS CS835769A patent/CS158259B2/cs unknown
- 1969-12-18 CH CH1883869A patent/CH514985A/de not_active IP Right Cessation
- 1969-12-19 RO RO61922A patent/RO56647A/ro unknown
- 1969-12-19 ES ES374739A patent/ES374739A1/es not_active Expired
- 1969-12-24 BG BG013604A patent/BG17438A3/xx unknown
-
1970
- 1970-01-06 LU LU60143D patent/LU60143A1/xx unknown
- 1970-01-16 IL IL33723A patent/IL33723A/xx unknown
- 1970-01-16 NL NL7000672.A patent/NL163097C/xx not_active IP Right Cessation
- 1970-01-19 JP JP45005006A patent/JPS491850B1/ja active Pending
- 1970-01-20 OA OA53836A patent/OA03207A/xx unknown
- 1970-01-20 IE IE76/70A patent/IE34001B1/xx unknown
- 1970-01-20 GB GB2703/70A patent/GB1300094A/en not_active Expired
- 1970-01-21 NO NO00218/70A patent/NO128742B/no unknown
- 1970-01-21 AT AT54470A patent/AT298146B/de not_active IP Right Cessation
- 1970-01-21 FR FR7002091A patent/FR2028876A1/fr active Pending
- 1970-01-21 SE SE7000713A patent/SE371081B/xx unknown
- 1970-01-22 BE BE744774D patent/BE744774A/xx not_active IP Right Cessation
- 1970-01-22 PH PH11102*UA patent/PH9385A/en unknown
-
1974
- 1974-04-20 CY CY74074A patent/CY740A/xx unknown
- 1974-12-30 MY MY96/74A patent/MY7400096A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1300094A (en) | 1972-12-20 |
| FR2028876A1 (no) | 1970-10-16 |
| DE1903817A1 (de) | 1970-08-27 |
| FI51648C (fi) | 1977-03-10 |
| SE371081B (no) | 1974-11-11 |
| DE1903817C3 (de) | 1981-06-25 |
| LU60143A1 (no) | 1970-03-06 |
| ES374739A1 (es) | 1972-01-16 |
| IE34001L (en) | 1970-07-22 |
| NL7000672A (no) | 1970-07-24 |
| IE34001B1 (en) | 1975-01-08 |
| RO56647A (no) | 1974-07-01 |
| FI51648B (no) | 1976-11-30 |
| OA03207A (fr) | 1970-12-15 |
| NL163097C (nl) | 1980-08-15 |
| DE1903817B2 (de) | 1980-08-21 |
| DK124656B (da) | 1972-11-13 |
| BG17438A3 (bg) | 1973-11-10 |
| IL33723A (en) | 1973-08-29 |
| AT298146B (de) | 1972-04-25 |
| NL163097B (nl) | 1980-03-17 |
| BE744774A (fr) | 1970-07-22 |
| IL33723A0 (en) | 1970-06-17 |
| CY740A (en) | 1974-04-20 |
| PH9385A (en) | 1975-10-22 |
| CH514985A (de) | 1971-11-15 |
| JPS491850B1 (no) | 1974-01-17 |
| MY7400096A (en) | 1974-12-31 |
| CS158259B2 (no) | 1974-10-15 |
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