NO118272B - - Google Patents
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- NO118272B NO118272B NO79268A NO79268A NO118272B NO 118272 B NO118272 B NO 118272B NO 79268 A NO79268 A NO 79268A NO 79268 A NO79268 A NO 79268A NO 118272 B NO118272 B NO 118272B
- Authority
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- Norway
- Prior art keywords
- active substance
- soil
- seed
- methyl
- plants
- Prior art date
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- 241000233866 Fungi Species 0.000 claims description 9
- 230000003032 phytopathogenic effect Effects 0.000 claims description 6
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 29
- 239000002689 soil Substances 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 7
- -1 petrol Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000005554 pickling Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000002464 fungitoxic effect Effects 0.000 description 4
- 230000035784 germination Effects 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-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
- 239000006004 Quartz sand Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MFKDULOUZDAXOD-UHFFFAOYSA-N 2-methyl-5-nitro-N-(trifluoromethyl)aniline Chemical compound FC(NC1=C(C=CC(=C1)[N+](=O)[O-])C)(F)F MFKDULOUZDAXOD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000813090 Rhizoctonia solani Species 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001529717 Corticium <basidiomycota> Species 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 208000012766 Growth delay Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 240000001931 Ludwigia octovalvis Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 241000865903 Thielaviopsis Species 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N47/02—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 no bond to a nitrogen atom
- A01N47/04—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 no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Triklormetylsulfenyl-N-(trifluormetyl)-N-(2-metyl-5-nitro- Trichloromethylsulfenyl-N-(trifluoromethyl)-N-(2-methyl-5-nitro-
anilid) for bekjempelse av fytopatogen sopp. anilid) for combating phytopathogenic fungi.
Oppfinnelsen vedrører triklormetylsulfenyl-N-(trifluor-metyl )-N-(2-metyl-5-nitroanilxd) Som har fungitoksiske egenskaper. The invention relates to trichloromethylsulfenyl-N-(trifluoromethyl)-N-(2-methyl-5-nitroanilxd) which has fungitoxic properties.
Det er allerede kjent at man kan anvende fluordiklor-metylsulfenyl-N-(trifluormetyl)-N-(2-metyl-5-nitroanilid) med formel It is already known that one can use fluorodichloromethylsulfenyl-N-(trifluoromethyl)-N-(2-methyl-5-nitroanilide) with the formula
på grunn av dets sterke fungitoksiske egenskaper til bekjempelse av fytopatogene sopp (sml. DAS 1.222.047). Det virksomme stoff egner Kfr. kl. 45 1-21/02 due to its strong fungitoxic properties to combat phytopathogenic fungi (cf. DAS 1.222.047). The active substance is suitable Kfr. at 45 1-21/02
seg spesielt som såvarebeisemiddel og som jordbehandlingsmiddel mot soppaktige plantesykdommer. especially as a seed dressing agent and as a soil treatment agent against fungal plant diseases.
Det virksomme stoff har imidlertid en betraktelig ulempe. Det har en for høy fytotoksisitet for mange planter. Det gjelder spesielt for bomull, tomater, nelliker, jordnøtter og bønner. Spesielt tungtveiende er denne ulempe for jordbehandlingen av bomulls-felter. Bomull er en av de økonomisk viktigste kulturplanter i verden og lider i sterk grad under angrep av fytopatogene jordsopp. Bomull behøver derfor ganske spesielt beskyttelse ved hjelp av fungicide midler, som imidlertid ikke bør utøve uheldige bivirk-ninger. However, the active substance has a considerable disadvantage. It has too high a phytotoxicity for many plants. This is especially true for cotton, tomatoes, cloves, peanuts and beans. This disadvantage is particularly weighty for the soil treatment of cotton fields. Cotton is one of the most economically important crops in the world and suffers greatly from attack by phytopathogenic soil fungi. Cotton therefore needs quite special protection by means of fungicidal agents, which, however, should not have adverse side effects.
Det ble funnet at det nye triklormetylsulfenyl-N-(tri-fluormetyl)-N-(2-metyl~5-nitroanilid ) med formel It was found that the new trichloromethylsulfenyl-N-(tri-fluoromethyl)-N-(2-methyl~5-nitroanilide) of formula
har sterk fungitoksisk virkning og er samtidig spesielt godt tålbart for planten. Man får triklormetylsulfenyl-N-anilid med formel II når man omsetter N-trifluormetyl-(2-metyl-5-nitroanilin) med formel has a strong fungitoxic effect and is at the same time particularly well tolerated by the plant. Trichloromethylsulfenyl-N-anilide with formula II is obtained when reacting N-trifluoromethyl-(2-methyl-5-nitroaniline) with formula
i nærvær av et tertiært amin med perklormetylmerkaptan med formel in the presence of a tertiary amine with perchloromethyl mercaptan of formula
ClS-CCl^ (IV) ClS-CCl^ (IV)
eventuelt i nærvær av et fortynningsmiddel. optionally in the presence of a diluent.
Det må anses som meget overraskende at forbindelse II ifølge oppfinnelsen er ganske betraktelig overlegen med hensyn til fytotoksisitet overfor den tidligere kjente forbindelse I som har samme fungicide virkning. It must be considered very surprising that compound II according to the invention is quite considerably superior in terms of phytotoxicity to the previously known compound I, which has the same fungicidal effect.
De som utgangsstoffer for omsetningen nødvendige for-bindelser er allerede kjent. The compounds required as starting materials for the turnover are already known.
Omsetningen kan foretas i nærvær av inerte organiske fortynningsmidler. Hertil hører fortrinnsvis hydrokarboner som bensin, toluen og benzen, etere som dietyleter og dioksan såvel som ketoner, f.eks. aceton. The reaction can be carried out in the presence of inert organic diluents. These preferably include hydrocarbons such as petrol, toluene and benzene, ethers such as diethyl ether and dioxane as well as ketones, e.g. acetone.
Som tertiære aminer kommer det på tale alle på vanlig måte som syrebindere anvendte tertiære aminer, f.eks. trimetylamin, trietylamin, dimetylanilin, dietylanilin og pyridin. Tertiary amines include all tertiary amines commonly used as acid binders, e.g. trimethylamine, triethylamine, dimethylaniline, diethylaniline and pyridine.
Reaksjonstemperaturene kan varieres innen et stort område. Vanligvis arbeider man mellom 0 og 80°C, fortrinnsvis mellom 10 og 50°C. The reaction temperatures can be varied within a large range. Usually, one works between 0 and 80°C, preferably between 10 and 50°C.
Ved gjennomføring av fremgangsmåten anvender man hensiktsmessig ca. 1 mol av sulfenkloridet til 1 mol anilin. Omsetningen kan f.eks. foregå således at man oppløser de to utgangsstoffer i et inert oppløsningsmiddel og langsomt tilsetter det tertiære amin. Opparbeidelsen foregår på vanlig måte, f.eks. ved frafiltrering av dannet aminhydroklorid og inndampning av filtratet i vakuum. When carrying out the procedure, it is appropriate to use approx. 1 mole of the sulfene chloride to 1 mole of aniline. The turnover can e.g. proceed in such a way that the two starting materials are dissolved in an inert solvent and the tertiary amine is slowly added. Processing takes place in the usual way, e.g. by filtering off the formed amine hydrochloride and evaporating the filtrate in vacuo.
Det virksomme stoff ifølge oppfinnelsen har sterke fungitoksiske virkninger og egner seg til bekjempelse av fytopatogen sopp. Spesielt er det egnet som såvarebeisemiddel og som jordbehandlingsmiddel, altså til bekjempelse av frøoverførbar sopp og sopp i jorden. Til disse to grupper hører spesielt sopp av slekten Tilletia, Helminthosporium, Rhizoctonia, Fusarium, Verticillium, Corticium og Thielaviopsis såvel som Pythium. The active substance according to the invention has strong fungitoxic effects and is suitable for combating phytopathogenic fungi. In particular, it is suitable as a seed dressing agent and as a soil treatment agent, i.e. for combating seed-borne fungi and fungi in the soil. To these two groups belong in particular fungi of the genus Tilletia, Helminthosporium, Rhizoctonia, Fusarium, Verticillium, Corticium and Thielaviopsis as well as Pythium.
Det virksomme stoff ifølge oppfinnelsen kan overføres i de vanlige formuleringer som oppløsninger, emulsjoner,, suspensjoner, pulvere, pastaer og granulater. Disse fremstilles på kjent måte, f.eks. ved sammenblanding av de virksomme stoffer med drøyemidler, altså flytende oppløsningsmidler og/eller faste bærestoffer, eventuelt under anvendelse av overflateaktive midler som emulgeringsmidler og/eller dispergeringsmidler. Anvendes vann som drøyemiddel kan det f.eks. også anvendes organiske oppløsningsmidler som hjelpeoppløsnings-midler. Som flytende oppløsningsmiddel kommer det i det vesentlige på tale: aromater som xylen og benzen, klorerte aromater som klor-benzener, parafiner som jordoljefraksjoner, alkoholer som metanol og butanol, sterkt polare oppløsningsmidler som dimetylformamid og dimetylsulfoksyd såvel som vann, som faste bærestoffer: naturlig stenmel som kaoliner, lerjord, talkum og kritt, og syntetiske stenmel som høydispergert kiselsyre og silikater, som emulgeringsmidler: ikke-ioniske og anioniske emulgatorer som polyoksyetylen-fettsyre-estere, polyoksyetylen-fettalkoholetere, f.eks. alkylaryl-polyglykol-eter, alkylsulfonater og arylsulfonater, som dispergeringsmiddel: The active substance according to the invention can be transferred in the usual formulations such as solutions, emulsions, suspensions, powders, pastes and granules. These are produced in a known manner, e.g. by mixing the active substances with emulsifiers, i.e. liquid solvents and/or solid carriers, possibly using surface-active agents such as emulsifiers and/or dispersants. If water is used as a suspending agent, it can e.g. organic solvents are also used as auxiliary solvents. As a liquid solvent, these are essentially: aromatics such as xylene and benzene, chlorinated aromatics such as chlorobenzenes, paraffins such as petroleum fractions, alcohols such as methanol and butanol, strongly polar solvents such as dimethylformamide and dimethylsulfoxide as well as water, as solid carriers: natural stone flours such as kaolins, clays, talc and chalk, and synthetic stone flours such as highly dispersed silicic acid and silicates, as emulsifiers: non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ether, alkylsulfonates and arylsulfonates, as dispersant:
f.eks. lignin, suifittavlut og metylcellulose. e.g. lignin, suifite liquor and methyl cellulose.
Det virksomme stoff ifølge oppfinnelsen kan foreligge i formuleringene i blanding med andre kjente virksomme stoffer som fungicider, insekticider, akaricider, nematodicider, beskyttelses-stoffer mot fugleangrep, vekststoffer, plantenæringsstoffer og jord-strukturforbedringsmidler. The active substance according to the invention can be present in the formulations in a mixture with other known active substances such as fungicides, insecticides, acaricides, nematocides, protective substances against bird attacks, growth substances, plant nutrients and soil structure improvers.
Formuleringene inneholder vanligvis mellom 1 og 95 > fortrinnsvis mellom 5 og 9^ vektprosent virksomt stoff. The formulations usually contain between 1 and 95 > preferably between 5 and 9% by weight of active substance.
De virksomme stoffer kan anvendes som sådanne i form av deres formuleringer eller av de herav ved ytterligere fortynning til-beredte anvendelsesformer, som bruksferdige oppløsninger, emulsjoner, suspensjoner, pulvere, pastaer og granulater. Anvendelsen foregår på vanlig måte, f.eks. ved helling, sprøyting, dusjing, forstøvning, The active substances can be used as such in the form of their formulations or of the application forms prepared from them by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. The application takes place in the usual way, e.g. by pouring, spraying, showering, atomizing,
strøing, tørrbeising, fuktebeising, våtbeising, slambeising eller inkrustering. spreading, dry pickling, wet pickling, wet pickling, mud pickling or incrustation.
Ved såvarebehandlingen anvendes vanligvis virksomme stoffmengder fra 0,1 til 10 g pr. kilo såvare, fortrinnsvis 0,5 g til 5 g« Til jordbehandling er det hensiktsmessig med virksomme stoffmengder fra 1 til 500 g pr. v? jord, fortrinnsvis 10-200 g. In the seed treatment, effective amounts of substances from 0.1 to 10 g per kilo of seed, preferably 0.5 g to 5 g" For soil treatment, it is appropriate to use effective amounts of substances from 1 to 500 g per w? soil, preferably 10-200 g.
Sammenligner man de fytotoksiske egenskaper av den tidligere kjente forbindelse I med fytotoksisiteten av forbindelse II ifølge oppfinnelsen, så fremkommer følgende bilde. If one compares the phytotoxic properties of the previously known compound I with the phytotoxicity of compound II according to the invention, the following picture emerges.
Til tilstrekkelig beskyttelse av bomull mot jordboende fytopatogensopp er det nødvendig i jorden å oppnå en konsentrasjon av forbindelse I eller forbindelse II på 50-100 mg/l for noen tid. Ved utbringning av de virksomme stoffer må man være oppmerksom på at det ikke alltid oppnås en helt jevn fordeling, og man får dermed lokale overdoseringer, som kan medføre skader på plantene. Av denne grunn er det meget viktig at en viss overdosering ikke er skadelig for kulturplantene. For adequate protection of cotton against soil-dwelling phytopathogenic fungi, it is necessary to achieve in the soil a concentration of compound I or compound II of 50-100 mg/l for some time. When applying the active substances, you must be aware that a completely even distribution is not always achieved, and you thus get local overdoses, which can cause damage to the plants. For this reason, it is very important that a certain overdose is not harmful to the cultivated plants.
En konsentrasjon på 50-100 mg/l av det virksomme stoff ifølge oppfinnelsen viser på bomull ingen influering på kimevnen, ingen kimehemming og heller ingen veksthemming. A concentration of 50-100 mg/l of the active substance according to the invention shows, on cotton, no influence on germination, no inhibition of germination and no inhibition of growth either.
I forhold til dette viser det tidligere kjente virksomme stoff I innvirkning på kimevnen med en ganske betraktelig kimefor-sinkning såvel som også en betraktelig vekstinfluering. In relation to this, the previously known active ingredient I shows an effect on the ability to germinate with a fairly considerable delay in germination as well as a considerable influence on growth.
Av denne sammenligning fremgår det entydig at det virksomme stoff ifølge oppfinnelsen er overlegen overfor det tidligere kjente virksomme stoff ved samme fungicide virkning på grunn av dets From this comparison, it is clear that the active substance according to the invention is superior to the previously known active substance for the same fungicidal effect due to its
mindre fytotoksisitet. less phytotoxicity.
Eksempel A. Example A.
Jordbehandlingsprøve / jordoverførte mykoser. Soil treatment test / soil-transmitted mycoses.
For fremstilling av en hensiktsmessig virksom stofftilberedning drøyer man det virksomme stoff med talkum til 5% virksomt stoffinnhold og deretter med kvartssand til 0,5% virksomt stoffinnhold. To prepare an appropriate active substance preparation, the active substance is mixed with talc to 5% active substance content and then with quartz sand to 0.5% active substance content.
Den virksomme stofftilberedning sammenblander man jevnt med Fruhstorfer-enhetsjord, som først er sterilisert og deretter er blitt podet med en renkultur av Rhizoctonia solani. Jorden fylles i potter og såes med 5 x 10 erter. Pottene oppstilles ved l8-22°C i veksthus og holdes normalt fuktige. 3 uker etter utsåing bestemmer man antallet sunne planter i % av utlagte frø. 0% betyr at det ikke er oppvokset noen sunne planter, 100% betyr at alle frø har gitt sunne planter. The active substance preparation is evenly mixed with Fruhstorfer unit soil, which has first been sterilized and then inoculated with a pure culture of Rhizoctonia solani. The soil is filled in pots and sown with 5 x 10 peas. The pots are set up at 18-22°C in a greenhouse and kept normally moist. 3 weeks after sowing, the number of healthy plants is determined as a % of the seeds sown. 0% means that no healthy plants have grown, 100% means that all seeds have produced healthy plants.
Virksomme stoffer, virksomme stoffkonsentrasjoner i jorden og resultatene-fremgår av følgende tabell: Active substances, active substance concentrations in the soil and the results are shown in the following table:
Eksempel B. Example B.
Såvarebeisemiddelprøve. Seed mordant test.
For fremstilling av et hensiktsmessig tørrbeisemiddel drøyer man det virksomme stoff med en blanding av like vektdeler talkum og kiselgur til en finpulverisert blanding med den ønskede virksomme stoffkonsentrasjon. To produce a suitable dry mordant, the active substance is ground with a mixture of equal parts by weight of talc and diatomaceous earth to a finely powdered mixture with the desired active substance concentration.
For beising ryster man såkornet med tørrbeiseniidlet i For pickling, shake the seed grain with the dry pickling needle in it
en lukket glassflaske. Såkornet sår man med ^ > x 10 korn i en potte, som inneholder Fruhstorfer-enhetsjord som først er blitt sterilisert og deretter podet med en renkultur av Rhizoctonia solani. Pottene oppstilles ved l8 - 22°C i veksthus og holdes normalt fuktige. 3 uker etter utsåing bestemmer man antallet av friske planter i % av utlagte frø. 0% betyr at det ikke er vokset opp noen friske planter, 100% betyr at det av alle frø er dannet friske planter. a closed glass bottle. The seed is sown with ^ > x 10 grains in a pot, which contains Fruhstorfer unit soil which has first been sterilized and then inoculated with a pure culture of Rhizoctonia solani. The pots are set up at l8 - 22°C in a greenhouse and are kept normally moist. 3 weeks after sowing, the number of healthy plants is determined as a % of the sown seeds. 0% means that no healthy plants have grown, 100% means that healthy plants have been formed from all seeds.
Virksomme stoffer, virksomme stoffkonsentrasjoner i beisemidlet, anvendte mengder av beisemidlet såvel som resultatene fremgår av følgende tabell: Active substances, active substance concentrations in the mordant, used quantities of the mordant as well as the results appear in the following table:
Eksempel C. Example C.
Plantetålbarhetsprøve / jordbehandling / bomull. Plant tolerance test / soil treatment / cotton.
Til fremstilling av en hensiktsmessig virksom stofftilberedning drøyer man det virksomme stoff til 5% virksomt stoffinnhold med talkum og deretter til 0,5% virksomt stoffinnhold med kvartssand. To prepare a suitable active substance preparation, the active substance is diluted to 5% active substance content with talc and then to 0.5% active substance content with quartz sand.
Den virksomme stofftilberedning sammenblander man jevnt med en jordblanding av 1 volumdel sterilisert leraktig åkerjord, 1 volumdel sterilisert kompostjord og 8 volumdeler sterilisert kvartssand. Jordblandingen fylles i såkasser og såes med 2 x 50 bomullsfrø. Kassene oppstilles ved temperaturer omtrent 22°C i veksthus og holdes normalt fuktige. 7 dager etter utsåing bestemmer man antallet oppvoksede planter i % av utlagte frø. De viser sammenlignet med ubehandlede kontroller, preparatbetingede oppvekstforsinkelser og eventuelt også vekstakselerering. Antall oppvokste planter på den 14. dag karak-teriserer kimevnen for såkornet under innvirkning på preparatet. The active substance preparation is evenly mixed with a soil mixture of 1 part by volume of sterilized clayey field soil, 1 part by volume of sterilized compost soil and 8 parts by volume of sterilized quartz sand. The soil mixture is filled in seed boxes and sown with 2 x 50 cotton seeds. The boxes are set up at temperatures of approximately 22°C in greenhouses and are normally kept moist. 7 days after sowing, the number of grown plants is determined as a % of the seeds laid out. Compared to untreated controls, they show preparation-related growth delays and possibly also growth acceleration. The number of grown plants on the 14th day characterizes the germination capacity of the seed under the influence of the preparation.
Den gjennomsnittlige plantehøyde såvel som den gjennomsnittlige The average plant height as well as the average
nye vekst av enkeltplantene viser innvirkningen på vekstintensiteten. Er disse fire enkeltverdier tydelig lavere enn de for ubehandlede kontrollkasser, så foreligger en fytotoksisk virkning av preparatet. new growth of the individual plants shows the impact on growth intensity. If these four individual values are clearly lower than those for untreated control boxes, then there is a phytotoxic effect of the preparation.
Eksempel 1. Example 1.
22 g 2-metyl-5-nitro-N-trifluormetylanilin.og 18,6 g perklormetylmerkaptan oppløses i 150 ml benzen og blandes ved værelsetemperatur under avkjøling med 11 g trietylamin. Man etter-omrører i kort tid, frasuger utfelt trietylaminhydroklorid og inn-damper benzenoppløsningen i vakuum. Man får som residuum 33 g triklormetylsulfenyl-N-(trifluormetyl)-N-(2-metyl-5-nitroanilid) med sm.p. 65 - 67°C (fra metanol). 22 g of 2-methyl-5-nitro-N-trifluoromethylaniline and 18.6 g of perchloromethylmercaptan are dissolved in 150 ml of benzene and mixed at room temperature while cooling with 11 g of triethylamine. The mixture is stirred for a short time, the precipitated triethylamine hydrochloride is sucked off and the benzene solution is evaporated in vacuo. You get 33 g as a residue trichloromethylsulfenyl-N-(trifluoromethyl)-N-(2-methyl-5-nitroanilide) with m.p. 65 - 67°C (from methanol).
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0051692 | 1967-03-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO118272B true NO118272B (en) | 1969-12-08 |
Family
ID=7104822
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO79268A NO118272B (en) | 1967-03-02 | 1968-03-01 |
Country Status (8)
Country | Link |
---|---|
AT (1) | AT279584B (en) |
BE (1) | BE711513A (en) |
DE (1) | DE1618375B1 (en) |
ES (1) | ES351116A1 (en) |
FR (1) | FR1555311A (en) |
GB (1) | GB1149937A (en) |
NL (1) | NL6802688A (en) |
NO (1) | NO118272B (en) |
-
1967
- 1967-03-02 DE DE19671618375 patent/DE1618375B1/en active Pending
-
1968
- 1968-01-31 GB GB501668A patent/GB1149937A/en not_active Expired
- 1968-02-21 AT AT164668A patent/AT279584B/en not_active IP Right Cessation
- 1968-02-26 NL NL6802688A patent/NL6802688A/xx unknown
- 1968-02-29 BE BE711513D patent/BE711513A/xx unknown
- 1968-03-01 ES ES351116A patent/ES351116A1/en not_active Expired
- 1968-03-01 FR FR1555311D patent/FR1555311A/fr not_active Expired
- 1968-03-01 NO NO79268A patent/NO118272B/no unknown
Also Published As
Publication number | Publication date |
---|---|
DE1618375B1 (en) | 1971-12-09 |
FR1555311A (en) | 1969-01-24 |
GB1149937A (en) | 1969-04-23 |
NL6802688A (en) | 1968-09-03 |
ES351116A1 (en) | 1969-06-01 |
BE711513A (en) | 1968-08-29 |
AT279584B (en) | 1970-03-10 |
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