DK141711B - Process for controlling undesired plant growth in crops of useful plants and preparation for use in carrying out the process. - Google Patents
Process for controlling undesired plant growth in crops of useful plants and preparation for use in carrying out the process. Download PDFInfo
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- DK141711B DK141711B DK462574AA DK462574A DK141711B DK 141711 B DK141711 B DK 141711B DK 462574A A DK462574A A DK 462574AA DK 462574 A DK462574 A DK 462574A DK 141711 B DK141711 B DK 141711B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
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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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
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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
- 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
- A01N37/18—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/20—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
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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
- 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
- A01N37/18—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/32—Cyclic imides of polybasic carboxylic acids or 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
- 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
- A01N37/36—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Description
(11) FREMLÆGGELSESSKRIFT 141711 DANMARK (61) Int el·3 A 01 N 47/12 UMmvΙΜΠΓν A 01 Η 47/16 // C 07 c 149/16 §(21) Ansegning nr. 4625/?4 (22) Indleveret den JO . aug. 1974 (23) Lebedeg 50. aug. 19?4 (44). Ansøgningen fremlagt og fremlæggelsewkriftet offentliggjort den 2 . jun. 1 980(11) PRESENTATION 141711 DENMARK (61) Int el · 3 A 01 N 47/12 UMmvΙΜΠΓν A 01 Η 47/16 // C 07 c 149/16 § (21) Application No. 4625 /? 4 (22) Filed on JO. August 1974 (23) Live 50 Aug. 19? 4 (44). The application submitted and the submission paper published on 2. June 1 980
DIREKTORATET FORDIRECTORATE OF
PATENT- OG VAREMÆRKEVÆSENET (30> begæret fra denTHE PATENT AND TRADEMARK BASIS (30> requested from it
4. Bep. 1975, 594250, US4. Bep. 1975, 594250, US
(71> STAUFFER CHEMICAL COMPANY, 1200 South 47th Street, Richmond, Cali* Tbrnia 94804, US.(71> STAUFFER CHEMICAL COMPANY, 1200 South 47th Street, Richmond, Cali * Tbrnia 94804, US.
i72) Opfinder: Duane Randall Arneklev, Antelope, Montana 59211, US: Don Robert Baker, 15 Muth DrTve, Orinda, California 94565, US.i72) Inventor: Duane Randall Arneklev, Antelope, Montana 59211, US: Don Robert Baker, 15 Muth DrTve, Orinda, California 94565, US.
(74) Fuldmægtig under eagene behandling:(74) Clerk of the Ego Process:
Firmaet Chas. Hude.The company Chas. Hude.
(54) Fremgangsmåde til bekæmpelse af uønsket plantevækst i afgrøder af nytteplanter samt præparat til anvendelse ved udførelse af fremgangs* måden.(54) Procedure for controlling undesirable plant growth in crops of crops and preparation for use in carrying out the procedure *.
Den foreliggende opfindelsen angår en fremgangsmåde til bekæmpelse af uønsket plantevækst i afgrøder af nytteplanter ved hjælp af et herbicid valgt blandt S-ethyl-diprdpylthiocarbamat og S-ethyl-hexahydroazepin-(1)-thiocarboxylat samt et præparat til anvendelse ved udførelse af fremgangsmåden.The present invention relates to a method for controlling undesirable plant growth in crops of utilitarian plants by means of a herbicide selected from S-ethyl-diprdyl pylthiocarbamate and S-ethyl-hexahydroazepine (1) -thiocarboxylate, and a composition for use in the process.
Blandt de mange i handelen gående herbicide forbindelser har thio= carbamaterne alene eller i blanding med andre herbicider, såsom triazinerne, nået en relativ stor kommerciel succes. Disse herbicider er umiddelbart toksiske over for et stort antal ukrudtsplanter 2 1417 11 i forskellige koncentrationer, som varierer med modstandsdygtigheden af ukrudtsplanterne. Nogle eksempler på disse forbindelser er beskrevet i U.S.A. patentskrifterne nr. 2.913.327, 3.037.853, 3.175.897, 3.185.720, 3.198.786 og 3.582.314. Det har i praksis vist sig, at anvendelsen af disse thiocarbamater som herbicider til afgrøder undertiden forårsager alvorlige skader på afgrødeplanten.Among the many commercially available herbicidal compounds, the thio carbamates alone or in admixture with other herbicides such as the triazines have achieved a relatively high commercial success. These herbicides are immediately toxic to a large number of weeds at various concentrations, which vary with the resistance of the weeds. Some examples of these compounds are described in U.S.A. U.S. Patent Nos. 2,913,327, 3,037,853, 3,175,897, 3,185,720, 3,198,786 and 3,582,314. In practice, it has been found that the use of these thiocarbamates as herbicides for crops sometimes causes serious damage to the crop plant.
Ved anvendelse i de anbefalede mængder i jorden til bekæmpelse af mange bredbladede ukrudtsplanter og græsser opstår der alvorlige misdannelser og forkrøblinger af afgrødesplanterne. Denne abnorme vækst hos afgrødesplanterne resulterer i tab af afgrødeudbytte. Hidtil gjorte forsøg på at overvinde dette problem involverer behandling af afgrødefrø med visse antagonistiske midler før plantning af frøene, se U.S.A. patentskrifterne nr. 3.131.509 og 3.564.768. Disse antagonistiske midler har ikke været særlig vellykkede. De ovennævnte patentskrifter eksemplificerer specielt behandlingen af frø under anvendelse af forbindelser af en anden kemisk klasse, hvilket ikke giver antydning om den foreliggende opfindelse.When used in the recommended amounts in the soil to control many broadleaf weeds and grasses, severe malformations and crippling of the crop plants occur. This abnormal growth of the crop plants results in loss of crop yield. Heretofore attempts to overcome this problem involve treating crop seeds with certain antagonistic agents before planting the seeds, see U.S.A. U.S. Patent Nos. 3,311,509 and 3,564,768. These antagonistic agents have not been very successful. Specifically, the aforementioned patents exemplify the treatment of seeds using compounds of another chemical class, which does not imply the present invention.
Det har nu vist sig, at planter kan beskyttes mod beskadigelser hidrørende fra S-ethyl-dipropylthiocarbamat og S-ethyl-hexahydroazepin-(l)-thiocarboxylat, alene eller i blanding med andre forbindelser, såsom 2-chlor-2',6'-diethyl-N-(methoxymethyl)acetanilid, og/eller at planternes tolerance over for de aktive forbindelser ifølge ovennævnte U.S.A. patentskrifter kan forøges i væsentlig grad.It has now been found that plants can be protected from damage from S-ethyl dipropylthiocarbamate and S-ethyl hexahydroazepine (1) thiocarboxylate, alone or in admixture with other compounds such as 2-chloro-2 ', 6' -diethyl-N- (methoxymethyl) acetanilide, and / or tolerance of the plants to the active compounds of the above-mentioned United States Patents can be substantially increased.
Den foreliggende opfindelse angår således en fremgangsmåde af den indledningsvis anførte art, som er ejendommelig ved, at man på plantestedet eller på plantefrøene før plantning i vilkårlig rækkefølge eller samlet tilfører eller påfører en effektiv mængde af herbicidet og fra ca. 0,01 til ca. 15 vægtdele pr. vægtdel thiocarbamather= 12 1 bicid af en modgiftforbindelse med formlen R -S-R , hvori R betegner alkenyl indeholdende 3-6 carbonatomer, chloralkenyl indeholdende 3-6 carbonatomer eller halogenalkyl indeholdende 1-4 carbon= 2 atomer, og R betegner alkyl indeholdende 1-4 carbonatomer, halogenalkyl indeholdende 1-4 carbonatomer, alkenyl indeholdende 3-6 carbon= atomer eller chloralkenyl indeholdende 3-6 carbonatomer.Thus, the present invention relates to a method of the kind set out in the preamble which is characterized by applying or applying an effective amount of the herbicide to the plant site or to the seed seeds before planting in random order or together. 0.01 to approx. 15 parts per weight part by weight of thiocarbamate = 12 liters of bicide of an antidote of formula R -SR wherein R represents alkenyl containing 3-6 carbon atoms, chloralkenyl containing 3-6 carbon atoms or haloalkyl containing 1-4 carbon = 2 atoms and R represents alkyl containing 1-4 carbon atoms, haloalkyl containing 1-4 carbon atoms, alkenyl containing 3-6 carbon atoms or chloralkenyl containing 3-6 carbon atoms.
De ved fremgangsmåden ifølge opfindelsen tilførte eller påførte modgiftforbindelser kan også indvirke på den normale herbicide virkning af forbindelserne af thiocarbamattypen og eventuelle yderligere 3 141711 herbicider, såsom herbicider af den substituerede acetanilidtype, med henblik på at gøre dem selektive i deres 'virkning. Uanset hvilken virkemåde, som forekommer, er den tilsvarende nyttige og ønskværdige virkning den fortsatte herbicide virkning af thiocarba* matet eller et yderligere herbicid samtidig med en ledsagende formindsket herbicid virkning på ønskede afgrødearter. Denne fordel og brugbarhed vil fremgå nærmere af det følgende.The antidotes applied or applied to the method of the invention may also affect the normal herbicidal action of the thiocarbamate-type compounds and any additional herbicides, such as the substituted acetanilide type herbicides, to make them selective in effect. Regardless of the mode of action, the correspondingly useful and desirable effect is the continued herbicidal effect of thiocarbamate or an additional herbicide together with a concomitant diminished herbicidal effect on desired crop species. This advantage and usefulness will become more apparent in the following.
Præparatet til anvendelse ved udførelse af fremgangsmåden ifølge opfindelsen, ved hvilken herbicid og modgift påføres samlet, er ejendommeligt ved,at det omfatter S-ethyl-dipropylthiocarbamat eller S-ethyl-hexahydroazepin-(1)-thiocarboxylat og pr. vægtdel herbicid forbindelse fra ca. 0,01 til ca. 15 vægtdele af en modgiftforbindel-12 1 se med formlen R -S-R , hvori R betegner alkenyl indeholdende 3-6 carbonatomer eller chloralkenyl indeholdende 3-6 carbonatomer eller halogenalkyl indeholdende 1-4 carbonatomer, og R betegner alkyi indeholdende 1-4 carbonatomer, halogenalkyl indeholdende 1-4 carbon= atomer, alkenyl indeholdende 3-6 carbonatomer eller chloralkenyl indeholdende 3-6 carbonatomer.The composition for use in carrying out the process of the invention in which herbicide and antidote are applied together is peculiar in that it comprises S-ethyl dipropylthiocarbamate or S-ethylhexahydroazepine (1) -thiocarboxylate and pr. part by weight of herbicide compound from ca. 0.01 to approx. 15 parts by weight of an antidote compound 12 of formula R -SR wherein R represents alkenyl containing 3-6 carbon atoms or chloralkenyl containing 3-6 carbon atoms or haloalkyl containing 1-4 carbon atoms and R represents alkyl containing 1-4 carbon atoms, haloalkyl containing 1-4 carbon = atoms, alkenyl containing 3-6 carbon atoms or chloralkenyl containing 3-6 carbon atoms.
Udtrykkene herbicidmodgift eller modgiftmængde skal derfor karakterisere det middel, som i sin virkning har tendens til at modvirke den normale skadelige herbicide reaktion, scan herbicidet ellers kunne fremkalde. Hvorvidt modgiften betegnes som et hjælpemiddel, hæmningsmiddel, beskyttelsesmiddel, sikringsmiddel eller lignende vil afhænge af den pågældende bestemte virkemåde. Virkemåden varierer, men den virkning, som ønskes, er resultatet af fremgangsmåden ved behandling af jorden, hvori en afgrødeplante skal plantes. Hidtil har der ikke eksisteret noget system, som har været tilfredsstillende til dette formål.The terms herbicide antidote or antidote should therefore characterize the agent which, in its effect, tends to counteract the normal harmful herbicidal response the scan the herbicide might otherwise elicit. Whether the antidote is designated as an aid, inhibitor, safeguard, safeguard or the like will depend on the particular mode of action in question. The mode of operation varies, but the effect desired is the result of the method of treating the soil in which a crop plant is to be planted. To date, no system has existed that has been satisfactory for this purpose.
De ved fremgangsmåden ifølge opfindelsen anvendte forbindelser med den ovennævnte formel kan fremstilles ved hjælp af flere forskellige fremgangsmåder afhængigt af udgangsmaterialerne.The compounds of the invention of the above formula used in the process of the invention can be prepared by several different methods depending on the starting materials.
Generel fremgangsmåde til fremstilling af allylsulfider.General Procedure for Preparation of Allyl Sulfides.
Det aktive halogenid (af allyltypen) opløses i isopropylalkohol eller et andet passende opløsningsmiddel, og natriumsulfid, nonahydrat, sqm er blevet groft formalet, tilsættes. Tilsætningen sker ved reduceret 141711 4 temperatur, ca. 15°C. Ved reaktionens afslutning fjernes udfældet natriumchlorid ved filtrering, og opløsningsmidlet fjernes i vakuum. Den tilbageværende rest optages i benzen og ether og vaskes med tre portioner vand. Opløsningen tørres, og opløsningsmidlet afdestilleres i vakuum.The active halide (of the allyl type) is dissolved in isopropyl alcohol or another suitable solvent and sodium sulfide, nonahydrate, sqm has been coarsely ground. The addition takes place at reduced temperature, approx. 15 ° C. At the end of the reaction, precipitated sodium chloride is removed by filtration and the solvent is removed in vacuo. The remaining residue is taken up in benzene and ether and washed with three portions of water. The solution is dried and the solvent is distilled off in vacuo.
Generel fremgangsmåde til fremstilling af blandede sulfider.General Procedure for Preparing Mixed Sulfides.
En organisk mercaptan opløses i et passende opløsningsmiddel, såsom dioxan, isopropylalkohol eller lignende. Der tilsættes natriumhy= droxidopløsning, og reaktionsblandingen opvarmes. Der tilsættes et aktivt organisk halogenid, og blandingen varmes under tilbagesvaling. Oparbejdningen sker ved hjælp af normale procedurer i form af ekstraktion, opløsningsmiddelfjernelse, destillation eller krystallisation.An organic mercaptan is dissolved in a suitable solvent such as dioxane, isopropyl alcohol or the like. Sodium hydroxide solution is added and the reaction mixture is heated. An active organic halide is added and the mixture is heated at reflux. The work-up is done by normal procedures in the form of extraction, solvent removal, distillation or crystallisation.
De ved fremgangsmåden ifølge opfindelsen benyttede modgiftforbindelser og deres fremstiling belyses nærmere i det følgende eksempel. Efter fremstillingseksemplet følger en tabel over forbindelser, som kan fremstilles i overensstemmelse med den beskrevne procedure. Forbindelserne er blevet tildelt numre, som benyttes til identifikation af forbindelserne i resten af beskrivelsen.The antidotes used in the process of the invention and their preparation are elucidated in the following example. Following the preparation example is a table of compounds which can be prepared in accordance with the procedure described. The compounds have been assigned numbers which are used to identify the compounds for the remainder of the specification.
EksempelExample
Fremstilling af bis-(3,3-dichlorallyl)-sulfid 1,1,3-trichlorpropen-l (1100 g, 7,5 mol) blev opløst i en liter iso-propanol, og natriumsulfid, nonahydrat (900 g, 3,75 mol), som var blevet pulveriseret groft, blev tilsat i løbet af en time ved 15°C. Blandingen blev omrørt ved 25-30°C i 3 timer og ved 50°C i 2 timer.Preparation of bis (3,3-dichloroallyl) sulfide 1,1,3-trichloropropene-1 (1100 g, 7.5 mol) was dissolved in one liter of iso-propanol and sodium sulfide, nonahydrate (900 g, 3 75 mol), which had been coarsely powdered, was added over an hour at 15 ° C. The mixture was stirred at 25-30 ° C for 3 hours and at 50 ° C for 2 hours.
Den fik lov at henstå natten over ved stuetemperatur. Det udfældede natriumchlorid blev filtreret fra, og opløsningsmidlet blev fjernet i vakuum. Den tilbageværende olie blev optaget i en blanding af en liter benzen og en liter ether og vasket med tre 400 ml portioner vand. Opløsningen blev tørret over magnesiumsulfat, og opløsningsmidlet blev fjernet i vakuum. Det tilbageværende opløsningsmiddel blev fjernet ved ca. 0,5 mm Hg. Der opnåedes en rødbrun væske, udbytte 853 g (90%). Formlen blev bekræftet ved hjælp af NMR-spektro-skopi. Produktet destillerede ved kogepunkt 75-77°C/35 mm Hg.It was allowed to stand overnight at room temperature. The precipitated sodium chloride was filtered off and the solvent removed in vacuo. The remaining oil was taken up in a mixture of one liter of benzene and one liter of ether and washed with three 400 ml portions of water. The solution was dried over magnesium sulfate and the solvent removed in vacuo. The remaining solvent was removed at ca. 0.5 mm Hg. A reddish brown liquid was obtained, yield 853 g (90%). The formula was confirmed by NMR spectroscopy. The product distilled at boiling point 75-77 ° C / 35 mm Hg.
5 1417115 141711
Tabel 1 i τ Kogepunkt R -S-R oc eller i 2 "iflTable 1 in τ Boiling point R -S-R oc or in 2 "ifl
Forbindelse nr. R-1- R* 1 CC12=CHCH2 CC12=CHCH2 75-77/35 mm Hg 2 CC12=CC1CH2 CH2CH3 1,5325 3 CH3CC1=CHCH2 CH3CC1-CHCH2 1,5387 4 CHC1=CHCH2 CHC1*CHCH2 1,5270 5 CH2-CHCH2 CH2*CHCai2 1,4850 6 CC12=CC1CH2 CC12=CC1CH2 1,5810 7 C1CH2CH2CH2 CH2CH2CH2c1 1,4828 8 C1-CH=CC1-CH, CH-CC1*CSC1 rød/brutt væskeCompound No. R-1- R * 1 CC12 = CHCH2 CC12 = CHCH2 75-77 / 35 mm Hg 2 CC12 = CC1CH2 CH2CH3 1.5325 3 CH3CC1 = CHCH2 CH3CC1-CHCH2 1.5387 4 CHC1 = CHCH2 CHC1 * CHCH2 1, 5270 5 CH2-CHCH2 CH2 * CHCai2 1.4850 6 CC12 = CC1CH2 CC12 = CC1CH2 1.5810 7 C1CH2CH2CH2 CH2CH2CH2c1 1.4828 8 C1-CH = CC1-CH, CH-CC1 * CSC1 red / broken liquid
Modgiftforbindelserne blev benyttet i effektive herbicide modgiftmaterialer indeholdende thiocarbamaterne i kombination med de ovenfor beskrevne modgiftforbindelser. De blev afprøvet på følgende måde.The antidotes were used in effective herbicidal antidotes containing the thiocarbamates in combination with the antidotes described above. They were tested as follows.
Procedure; Multlafgrøde-modgiftbeskyttelse.Procedure; Multlafgrøde-modgiftbeskyttelse.
Plantekasser blev fyldt med Felton-lerblandet sandjord. En varietet af græs og bredbladede afgrøder blev benyttet til disse forsøg.Plant boxes were filled with Felton clay mixed sandy soil. A variety of grasses and broadleaf crops were used for these experiments.
EPTAM ® (EPTC) blev inkorporeret med 0,56, 3,36 eller 5,6 kg/ha, idet en konstant mængde på 5,6 kg/ha af modgiften blev benyttet.EPTAM ® (EPTC) was incorporated at 0.56, 3.36 or 5.6 kg / ha using a constant amount of 5.6 kg / ha of the antidote.
EPTAM® (EPTC) eller ORDRAM ® (S-ethyl-hexahydroazepin- (1) —thiocarb= oxylat) og den pågældende herbicidmodgift blev nu påført separat ved pipettering af afmålte mængder af de behørige stamopløsninger til jorden under indføring af denne i en 20 liter roterende cementblandér.EPTAM® (EPTC) or ORDRAM® (S-ethylhexahydroazepine (1) -thiocarb = oxylate) and the relevant herbicide antidote were now applied separately by pipetting metered amounts of the appropriate stock solutions to the soil while introducing it into a 20 liter rotary cement mixer.
Stamopløsningerne blev fremstillet som følger: A. 0,56 kg/ha: 670 mg EPTC 6E (75,5% a.i.) fortyndes med 500 ml de-ioniseret vand, således at 2 ml svarer til 0,56 kg/ha plantekasse.The stock solutions were prepared as follows: A. 0.56 kg / ha: Dilute 670 mg of EPTC 6E (75.5% a.i.) with 500 ml of deionized water so that 2 ml corresponds to 0.56 kg / ha of plant box.
B. 5,6 kg/ha: 6700 mg EPTC 6E (75,5% a.i.) fortyndes med 500 ml de-ionlseret vand, således at 2 ml svarer til 5,6 kg/ha plantekasse.B. 5.6 kg / ha: Dilute 6700 mg of EPTC 6E (75.5% a.i.) with 500 ml of deionized water so that 2 ml corresponds to 5.6 kg / ha of plant box.
C. 6,72 kg/ha: 4312 mg ORDRAM 6E (71,3% a.i.) blev fortyndet med 500 ml deioniseret vand, således at 4 ml af stamopløsningen svarer til 6,72 kg/ha ved tilførsel til en plantekasse.C. 6.72 kg / ha: 4312 mg of ORDRAM 6E (71.3% a.i.) was diluted with 500 ml of deionized water so that 4 ml of the stock solution corresponds to 6.72 kg / ha when applied to a plant box.
141711 6141711 6
Modgift-stamopløsninger fremstilles ved fortynding af 102 mg teknisk materiale med 10 ml acetone med 1% Tween 20 ® (polyoxyethylensorbitan— monolaurat), så at 2 ml svarer til 5,6 kg/ha plantekasse.Antidote stock solutions are prepared by diluting 102 mg of technical material with 10 ml of acetone with 1% Tween 20 ® (polyoxyethylene sorbitan monolaurate) to 2 ml corresponding to 5.6 kg / ha plant box.
Efter behandling af jorden med såvel herbicid som additiv overføres jorden fra blanderen til plantekassen, hvor den forberedes til til-såning. Begyndelsestrinnet ved forberedelsen består i at fjerne ca. 1/2 liter jordprøve fra hver plantekasse med henblik på tilbageholdelse og anvendelse til tildækning af frøene efter plantning. Derpå . udjævnes jorden, og 6 mm dybe furer frembringes i hver plantekasse. Plantekasser, som er behandlet med 5,6 kg/ha EPTAM, tilsåes med majs (Zea maize) og solsikke (Helianthus annus). Plantekasser behandlet med 0,56 kg/ha EPTAM tilsåes med durra (Sorghum vulgare), r^s (Dryaa sativa) og byg (Hordeum vulgare). Frøene dækkes derpå med den ca.. halve liter jordprøve, som er blevet fjernet før såning.After treating the soil with both herbicide and additive, the soil is transferred from the mixer to the plant box where it is prepared for sowing. The initial step in the preparation consists of removing approx. 1/2 liter soil sample from each plant box for retention and use to cover the seeds after planting. Then. the soil is leveled and 6 mm deep grooves are produced in each plant box. Plant boxes treated with 5.6 kg / ha EPTAM are sown with maize (Zea maize) and sunflower (Helianthus annus). Plant boxes treated with 0.56 kg / ha EPTAM are sown with sorghum (Sorghum vulgare), r ^ s (Dryaa sativa) and barley (Hordeum vulgare). The seeds are then covered with the approximately half liter of soil sample that has been removed before sowing.
Planteka s s erne placeres derpå på væksthusbænke, hvor temperaturerne holdes mellem ca. 21°C og ca. 32°C, Jorden vandes ved påsprøjtning til sikring af god plantevækst.The plants are then placed on greenhouse benches where temperatures are kept between approx. 21 ° C and approx. 32 ° C, The soil is watered by spraying to ensure good plant growth.
Beskadigelsesvurderinger foretages 3 eller 4 uger efter, at behandlingerne er udført. Jord behandlet med herbiciderne alene i mængder på 0,56, 3,36, 5,6 eller 6,72 kg/ha er medtaget for at give en basis for bestemmelse af omfanget af beskadigelsesreduktion, som tilvejebringes ved hjælp af herbicidroodgiftene. Den procentiske beskyttelse bestemmes ved en sammenligning med plantekasser, der ikke er behandlet med den pågældende modgift, men med herbicidet alene. Resultaterne er opført i tabel 2.Damage assessments are made 3 or 4 weeks after the treatments are completed. Soils treated with the herbicides alone in amounts of 0.56, 3.36, 5.6 or 6.72 kg / ha are included to provide a basis for determining the extent of damage reduction provided by the herbicide root poisons. The percentage protection is determined by a comparison with plant boxes not treated with the antidote in question, but with the herbicide alone. The results are listed in Table 2.
η 1-4171 1η 1-4171 1
Tabel 2Table 2
Multiafgrøde-beskyttelsesresultater Procent beskyttelseMulti crop protection results Percent protection
Herbicid Modgift % beskyt-Herbicide Antidote% Protect-
Forbindelse mængde mængde telse _nr. kg/ha kg/ha Afgrøde (4 uger) 1 EPTCa 0,56 5,6 durra X00 EPTC 0,56 5,6 ris 30 EPTC , 3,36 5,6 majs 100 ORDRAJT 6,72 5,6 ris 72 2 EPTC 3,36 5,6 sennep 100 3 EPTC 0,56 5,6 durra 50 EPTC 0,56 5,6 ris 30 EPTC 3,36 5,6 . majs 6/ 4 eptc 5,6 5,6 solsikke 67 *) 5 EPTC 0,56 5,6 ris 100 *) ORDRAM 6,72 5,6 ris 30 6 EPTC 0,56 1,12 ' ris 11 7 EPTC 0,56 5,6 byg 45 8 EPTC 5,6 5,6 majs 15 a = S-ethyl-dipropylthiocarbamat b = S-ethyl- hexahydroazepin-(1)-thiocarbpxylat· t) procent beskyttelse i 3 uger.Connection quantity quantity quantity no. kg / ha kg / ha Crop (4 weeks) 1 EPTCa 0.56 5.6 durra X00 EPTC 0.56 5.6 rice 30 EPTC, 3.36 5.6 corn 100 ORANGE 6.72 5.6 rice 72 2 EPTC 3.36 5.6 mustard 100 3 EPTC 0.56 5.6 sorghum 50 EPTC 0.56 5.6 rice 30 EPTC 3.36 5.6. corn 6/4 eptc 5.6 5.6 sunflower 67 *) 5 EPTC 0.56 5.6 rice 100 *) ORDRAM 6.72 5.6 rice 30 6 EPTC 0.56 1.12 'rice 11 7 EPTC 0 , 56 5.6 barley 45 8 EPTC 5.6 5.6 corn 15 a = S-Ethyl dipropylthiocarbamate b = S-Ethylhexahydroazepine (1) -thiocarbpxylate (t) percent protection for 3 weeks.
Modgiftforbindelserne og præparaterne ifølge opfindelsen kan benyttes i en hvilken som helst passende form. Modgiftforbindelserne kan således indgå i emulgerbare væsker eller koncentrater samt foreligge i form af væsker, befugtelige pulvere, puddere, granulære masser eller en hvilken som helst anden passende form. I sin foretrukne form er en ikke-fytotoksisk mængde af en herbicidmodgiftforbindelse blandet med et udvalgt herbicid og inkorporeret i jorden før plantning af frøene. Det må imidlertid forstås, at betbiciderne kan inkorporeres i jorden, og at modgiftforbindelsen derefter· kan inkorporeres i jorden. Selve afgrødefrøene kan endvidere behandles med en ikke-fytotoksisk mængden af forbindelsen Og plantes i jorden, som er blevet behandlet med herbicider, eller som er ubehandlet med herbicid og derefter behandles med herbicidet. Tilsætningen af modgiftforbin U1711 8 delsen påvirker ikke herbicidernes herbicide virkning på den uønskede plantevækst- Mængden af tilstedeværende modgiftforbindelse kan ligge mellem ca.The antidotes and compositions of the invention can be used in any suitable form. The antidote compounds may thus be contained in emulsifiable liquids or concentrates and may be in the form of liquids, wettable powders, powders, granular masses or any other suitable form. In its preferred form, a non-phytotoxic amount of a herbicide antidote is mixed with a selected herbicide and incorporated into the soil prior to planting the seeds. However, it is to be understood that the betbicides can be incorporated into the soil and that the antidote can then be incorporated into the soil. Furthermore, the crop seeds themselves can be treated with a non-phytotoxic amount of the compound and planted in soil that has been treated with herbicides or that has been treated with herbicide and then treated with the herbicide. The addition of the antidote compound U1711 8 does not affect the herbicidal effect of the herbicides on the undesired plant growth.
0,01 og ca. 15 vægtdele modgiftforbindelse som her beskrevet pr. vægtdel herbicid. Den nøjagtige mængde modgiftforbindelse vil sædvanligvis blive bestemt af økonomiske forhold for den mest effektive brugbare mængde. Det må forstås, at en ikke-fytotoksisk mængde af modgiftforbindelsen vil blive benyttet i de her beskrevne herbicide præparater.0.01 and approx. 15 parts by weight of antidote as described herein. part by weight of herbicide. The exact amount of antidote will usually be determined by economic conditions for the most effective amount of use. It is to be understood that a non-phytotoxic amount of the antidote will be used in the herbicidal compositions described herein.
De i tabellerne og andetsteds angivne herbicider benyttes i mængder, som vil frembringe en effektiv bekæmpelse af uønsket vegetation. Mængderne ligger inden for de anbefalede mængder, som er angivet af leverandøren. Ukrudtsbekæmpelsen er derfor i hvert tilfælde kommercielt acceptabel inden for det ønskede eller det anbefalede omfang.The herbicides listed in the tables and elsewhere are used in quantities which will produce an effective control of undesirable vegetation. The quantities are within the recommended quantities specified by the supplier. The control of weeds is therefore in every case commercially acceptable within the desired or recommended extent.
Det er klart, at de her"beskrevne og illustrerede herbicide midler er karakteriseret som effektive herbicider, som udviser en sådan aktivitet. Graden af denne herbicide aktivitet er forskellig for forbindelserne og varierer mellem kombinationer mængdemæssigt af forbindelserne. På lignende måde varierer aktivitetsgraden i et vist omfang blandt arterne af planter, hvortil en bestemt herbicid forbindelse eller herbicid kombination kan anvendes. Valget af den herbicide forbindelse eller herbicide kombination til bekæmpelse af uønskede plantearter kan således let foretages. Inden for den foreliggende opfindelses rammer kan forhindring af beskadigelse af en bestemt afgrødeart opnås ved tilstedeværelse af en bestemt forbindelse eller kombination.It is to be understood that the herbicidal agents described and illustrated herein are characterized as effective herbicides which exhibit such activity. The degree of this herbicidal activity is different for the compounds and varies between combinations in terms of the compounds. Thus, the choice of the herbicidal compound or herbicidal combination to control undesirable plant species can be readily accomplished. Within the scope of the present invention, prevention of damage to a particular crop species can be achieved. in the presence of a particular compound or combination.
De herbicide forbindelser, som benyttes ved udøvelsen af opfindelsen, er aktive herbicider af en generel type. Det vil sige, at de er herbicidt effektive mod en lang række plantearter, uden at der skelnes mellem ønskede og uønskede arter. Fremgangsmåden ved bekæmpelse af vegetation omfatter påføring af en herbicidt effektiv mængde af de her beskrevne herbicide forbindelser på det areal eller plantested, hvor bekæmpelse ønskes. Præparaterne ifølge opfindelsen indbefatter sådanne, hvori de to aktive herbicide forbindelser er udvalgt blandtThe herbicidal compounds used in the practice of the invention are active herbicides of a general type. That is, they are herbicidal effective against a wide variety of plant species, without distinguishing between desired and undesirable species. The method of combating vegetation comprises applying a herbicidal effective amount of the herbicidal compounds described herein to the area or plant site where control is desired. The compositions of the invention include those wherein the two active herbicidal compounds are selected from
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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DK310476A DK142932C (en) | 1973-09-04 | 1976-07-09 | PROCEDURE FOR PROTECTING A CROP OF DAMAGE FROM DAMAGE FROM A SUBSTITUTED ACETANILIDE HERBICIDE AND ACETANILIDE HERBICIDE FOR USING THE PROCEDURE |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US39423073A | 1973-09-04 | 1973-09-04 | |
US39423073 | 1973-09-04 |
Publications (3)
Publication Number | Publication Date |
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DK462574A DK462574A (en) | 1975-05-05 |
DK141711B true DK141711B (en) | 1980-06-02 |
DK141711C DK141711C (en) | 1980-10-27 |
Family
ID=23558086
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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DK462574AA DK141711B (en) | 1973-09-04 | 1974-08-30 | Process for controlling undesired plant growth in crops of useful plants and preparation for use in carrying out the process. |
DK310476A DK142932C (en) | 1973-09-04 | 1976-07-09 | PROCEDURE FOR PROTECTING A CROP OF DAMAGE FROM DAMAGE FROM A SUBSTITUTED ACETANILIDE HERBICIDE AND ACETANILIDE HERBICIDE FOR USING THE PROCEDURE |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
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DK310476A DK142932C (en) | 1973-09-04 | 1976-07-09 | PROCEDURE FOR PROTECTING A CROP OF DAMAGE FROM DAMAGE FROM A SUBSTITUTED ACETANILIDE HERBICIDE AND ACETANILIDE HERBICIDE FOR USING THE PROCEDURE |
Country Status (22)
Country | Link |
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JP (1) | JPS562523B2 (en) |
AR (1) | AR214035A1 (en) |
BE (1) | BE819489A (en) |
BG (1) | BG25191A3 (en) |
BR (1) | BR7406946D0 (en) |
CA (1) | CA1040450A (en) |
CH (1) | CH598751A5 (en) |
CS (1) | CS181770B2 (en) |
DD (1) | DD112892A5 (en) |
DE (1) | DE2441741C2 (en) |
DK (2) | DK141711B (en) |
FR (1) | FR2242028B1 (en) |
GB (2) | GB1459111A (en) |
HU (2) | HU175830B (en) |
IL (1) | IL45583A (en) |
IN (1) | IN139467B (en) |
IT (1) | IT1050240B (en) |
MX (1) | MX6146E (en) |
MY (2) | MY7700329A (en) |
NL (1) | NL176738C (en) |
PH (1) | PH11676A (en) |
TR (1) | TR18303A (en) |
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HU195398B (en) * | 1986-06-26 | 1988-05-30 | Eszakmagyar Vegyimuevek | Preparation comprising nitrile derivative antidote alone or with herbicidal active ingredient(s) |
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US3235368A (en) * | 1962-04-25 | 1966-02-15 | Monsanto Co | Stabilization of herbicide |
CA1174865A (en) * | 1971-04-16 | 1984-09-25 | Ferenc M. Pallos | Thiolcarbamate herbicides containing nitrogen containing antidote |
-
1974
- 1974-08-15 PH PH16172A patent/PH11676A/en unknown
- 1974-08-19 FR FR7428401A patent/FR2242028B1/fr not_active Expired
- 1974-08-21 BR BR6946/74A patent/BR7406946D0/en unknown
- 1974-08-23 GB GB3711474A patent/GB1459111A/en not_active Expired
- 1974-08-23 GB GB1220976A patent/GB1459112A/en not_active Expired
- 1974-08-28 CA CA208,002A patent/CA1040450A/en not_active Expired
- 1974-08-30 DK DK462574AA patent/DK141711B/en not_active IP Right Cessation
- 1974-08-30 CH CH1184274A patent/CH598751A5/xx not_active IP Right Cessation
- 1974-08-30 DE DE2441741A patent/DE2441741C2/en not_active Expired
- 1974-09-02 TR TR18303A patent/TR18303A/en unknown
- 1974-09-02 IN IN1967/CAL/74A patent/IN139467B/en unknown
- 1974-09-02 IT IT52828/74A patent/IT1050240B/en active
- 1974-09-02 DD DD180861A patent/DD112892A5/xx unknown
- 1974-09-03 CS CS7400006058A patent/CS181770B2/en unknown
- 1974-09-03 IL IL45583A patent/IL45583A/en unknown
- 1974-09-03 HU HU74SA3087A patent/HU175830B/en unknown
- 1974-09-03 HU HU74SA2688A patent/HU173775B/en unknown
- 1974-09-03 NL NLAANVRAGE7411682,A patent/NL176738C/en not_active IP Right Cessation
- 1974-09-03 MX MX746264U patent/MX6146E/en unknown
- 1974-09-03 BE BE148168A patent/BE819489A/en not_active IP Right Cessation
- 1974-09-03 AR AR255434A patent/AR214035A1/en active
- 1974-09-04 JP JP10183474A patent/JPS562523B2/ja not_active Expired
- 1974-09-04 BG BG027623A patent/BG25191A3/en unknown
-
1976
- 1976-07-09 DK DK310476A patent/DK142932C/en not_active IP Right Cessation
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1977
- 1977-12-30 MY MY329/77A patent/MY7700329A/en unknown
- 1977-12-30 MY MY328/77A patent/MY7700328A/en unknown
Also Published As
Publication number | Publication date |
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DE2441741A1 (en) | 1975-03-13 |
DK310476A (en) | 1976-07-09 |
NL176738B (en) | 1985-01-02 |
TR18303A (en) | 1977-01-07 |
MY7700329A (en) | 1977-12-31 |
BR7406946D0 (en) | 1975-07-01 |
DD112892A5 (en) | 1975-05-12 |
FR2242028A1 (en) | 1975-03-28 |
IT1050240B (en) | 1981-03-10 |
AR214035A1 (en) | 1979-04-30 |
GB1459112A (en) | 1976-12-22 |
CS181770B2 (en) | 1978-03-31 |
PH11676A (en) | 1978-05-19 |
CH598751A5 (en) | 1978-05-12 |
DK141711C (en) | 1980-10-27 |
DK142932B (en) | 1981-03-02 |
JPS562523B2 (en) | 1981-01-20 |
JPS5049433A (en) | 1975-05-02 |
BE819489A (en) | 1975-03-03 |
IL45583A0 (en) | 1974-11-29 |
DE2441741C2 (en) | 1984-10-04 |
GB1459111A (en) | 1976-12-22 |
FR2242028B1 (en) | 1977-11-04 |
IL45583A (en) | 1977-10-31 |
MX6146E (en) | 1984-11-28 |
DK142932C (en) | 1981-09-28 |
HU175830B (en) | 1980-10-28 |
HU173775B (en) | 1979-08-28 |
DK462574A (en) | 1975-05-05 |
NL176738C (en) | 1985-06-03 |
CA1040450A (en) | 1978-10-17 |
IN139467B (en) | 1976-06-19 |
NL7411682A (en) | 1975-03-06 |
MY7700328A (en) | 1977-12-31 |
AU7293374A (en) | 1976-03-11 |
BG25191A3 (en) | 1978-08-10 |
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