DK142932B - PROCEDURE FOR THE PROTECTION OF A CROP WITH DAMAGE FROM A SUBSTITUTED SCETANILIDE HERBICIDE AND ACETANILIDE HERBICIDE FOR USING THE PROCEDURE - Google Patents
PROCEDURE FOR THE PROTECTION OF A CROP WITH DAMAGE FROM A SUBSTITUTED SCETANILIDE HERBICIDE AND ACETANILIDE HERBICIDE FOR USING THE PROCEDURE Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- 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
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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
- A01N37/36—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
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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
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Description
i 142932in 142932
Den foreliggende opfindelse angår en fremgangsmåde til beskyttelse af en afgrøde mod beskadigelse hidrørende fra et substitueret acetanilidherbicid med formlen 9 C-CH-C1 <°K.The present invention relates to a method of protecting a crop from damage resulting from a substituted acetanilide herbicide of formula 9 C-CH-C1 <° K.
C H 2n5 3 5 hvori R er ethyl eller methyl og R er C_ .-alkoxyalkyl eller 0 -CH2b-OC2H5.Wherein R is ethyl or methyl and R is C1-6 alkoxyalkyl or O -CH2b-OC2H5.
Det har vist sig, at planter kan beskyttes mod beskadigelser hidrørende fra forskellige herbicider af den substituerede acetanilidtype, alene eller i blanding med andre for-10 bindeiser, og/eller at planternes tolerance over for de aktive forbindelser kan forøges i væsentlig grad ved hjælp af fremgangsmåden ifølge opfindelsen, der er ejendommelig ved, at man på plantestedet eller på plantefrøene før plantning henholdsvis tilfører eller påfører fra ca. 0,01 til ca. 15 15 vægtdele pr. vægtdel acetanilidherbicid af en modgiftfor- 12 1 bindelse med formlen R -S-R , hvori R betegner chloralkenyl med 3-6 carbonatomer eller halogenalkyl med 1-6 carbonatomer, 2 og R betegner halogenalkyl med 1-4 carbonatomer eller chlor» alkenyl med 3-6 carbonatomer.It has been found that plants can be protected from damage caused by various herbicides of the substituted acetanilide type, alone or in admixture with other compounds, and / or that the tolerance of the plants to the active compounds can be substantially increased by The method according to the invention, characterized in that, at the planting site or on the plant seeds, prior to planting, respectively, feed or apply from approx. 0.01 to approx. 15 15 parts by weight per unit weight. by weight of acetanilide herbicide of an antidote compound of formula R -SR wherein R represents chloralkenyl of 3-6 carbon atoms or haloalkyl of 1-6 carbon atoms, 2 and R represents haloalkyl of 1-4 carbon atoms or chloro alkenyl of 3-6 carbon atoms.
20 De forskellige substituentgrupper har følgende betydninger:The various substituent groups have the following meanings:
For Rx omfatter chloralkenyl mono-, di-, tri- og tetrachlor- substitution i alkenyIdele med 3 til 6 carbonatomer inklusive.For Rx, chloralkenyl includes mono-, di-, tri- and tetrachloro substitution in alkenyl moieties having 3 to 6 carbon atoms inclusive.
22
For R omfatter chloralkenyl mono-, di-, tri- og tetrachlor-substitution i alkenyldelen med 3 til 6 carbonatomer inklu-25 sive. Udtrykket halogenalkyl indbefatter fortrinsvis sådanne alkylgrupper, der er substitueret med mindst et halogenatom, som kan være chlor eller brom, og har fra 1 til 4 carbonatomer .For R, chloralkenyl comprises mono-, di-, tri- and tetrachloro-substitution in the alkenyl moiety having 3 to 6 carbon atoms inclusive. The term haloalkyl preferably includes such alkyl groups which are substituted by at least one halogen atom which may be chlorine or bromine and has from 1 to 4 carbon atoms.
2 1429322 142932
En udførelsesform for fremgangsmåden ifølge opfindelsen er karakteriseret ved, at det substituerede acetanilidherbicid er 2-chlor-2', 6'-diethyl-N-(methoxymethyl)acetanilid. Det har vist sig, at dette herbicids herbicide virkning særlig 5 godt modvirkes eller modificeres af modgiftforbindelserne ved fremgangsmåden ifølge opfindelsen.An embodiment of the process according to the invention is characterized in that the substituted acetanilide herbicide is 2-chloro-2 ', 6'-diethyl-N- (methoxymethyl) acetanilide. It has been found that the herbicidal effect of this herbicide is particularly well counteracted or modified by the antidotes of the method of the invention.
De ved fremgangsmåden ifølge opfindelsen tilførte eller påførte modgiftforbindelser kan også indvirke på den normale herbicide virkning af forbindelserne af typen substitueret 10 acetanilid 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 det substituerede acetanilid samtidig med den ledsagende formindskede herbicide virkning på øn-15 skede afgrødearter. Denne fordel og brugbarhed vil fremgå nærmere af det følgende.The antidotes added or applied to the process according to the invention may also affect the normal herbicidal action of the substituted acetanilide type compounds in order to make them selective in their effect. Regardless of the mode of action, the correspondingly useful and desirable effect is the continued herbicidal effect of the substituted acetanilide at the same time as the attendant diminished herbicidal effect on desired crop species. This advantage and usefulness will become more apparent in the following.
Opfindelsen angår endvidere acetanilidherbicider til anvendelse ved udførelsen af fremgangsmåden ifølge opfindelsen.The invention further relates to acetanilide herbicides for use in carrying out the process of the invention.
Acetanilidherbiciderne er ejendommelige ved, at de omfatter 20 en blanding af et acetanilidherbicid med formlenThe acetanilide herbicides are peculiar in that they comprise a mixture of an acetanilide herbicide of the formula
OISLAND
il R yC-CH-Clil R yC-CH-Cl
CC
hvori R er ethyl eller methyl, og R3 er C. -alkoxyalkyl eller -O 4 CH2C-OC2H5, og pr. vægtdel af herbicidet fra ca. 0,01 til ca.wherein R is ethyl or methyl and R3 is C1-4 alkoxyalkyl or -O4 CH2C-OC2H5; part by weight of the herbicide from approx. 0.01 to approx.
3 142932 1 2 15 vægtdele af en modgiftforbindelse med formlen R -S-R , hvori R^" betegner chloralkenyl med 3-6 carbonatomer eller 2 halogenalkyl med 1-6 carbonatomer, og R betegner halogen-alkyl med 1-4 carbonatomer eller chloralkenyl med 3-6 car-5 bonatomer.3 parts by weight of an antidote compound of the formula R -SR wherein R 2 -6 car-5 bon atoms.
Udtrykkene herbicid, modgift eller anti-modgiftmaengde skal derfor beskrive den virkning, som har tendens til at modvirke den normale skadelige herbicide reaktion, som herbicidet ellers kunne fremkalde. Hvorvidt det skal betegnes 10 som et hjælpemiddel, haonningsmiddel, 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 plantefrø i jorden, i hvilken en afgrødeplante er plan-15 tet. Hidtil har der ikke eksisteret noget system, som har været tilfredsstillende til dette formål.The terms herbicide, antidote, or antidote should therefore describe the effect that tends to counteract the normal harmful herbicide response that the herbicide might otherwise elicit. Whether it should be referred to as an aid, honey, safeguard, safeguard or the like will depend on the particular mode of action in question. The mode of action varies, but the effect desired is the result of the method of treating plant seeds in the soil in which a crop plant is planted. To date, no system has existed that has been satisfactory for this purpose.
En modgiftforbindelse med ovennævnte formål til anvendelse ved fremgangsmåden ifølge opfindelsen kan fremstilles ved hjælp af flere forskellige fremgangsmåder afhængigt af 20 udgangsmaterialerne.An antidote compound of the above purpose for use 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 Preparing Allyl Sulfides.
Det aktive halogenid (af allyltypen) opløses i isopropyl= alkohol eller et andet passende opløsningsmiddel, og natri= umsulfid, nonahydrat, som er blevet groft formalet, tilsæt-25 tes. Tilsætningen sker ved reduceret temperatur, ca. 15°c.The active halide (of the allyl type) is dissolved in isopropyl = alcohol or another suitable solvent and sodium sulfide, nonahydrate, which has been coarsely ground, is added. Addition at reduced temperature, approx. 15 ° C.
Ved reaktionens afslutning fjernes udfældet natriumchlorid ved filtrering, og opløsningsmidlet fjernes i vakuum. Den 4 142932 tilbageværende rest optages i benzen og ether og vaskes med tre portioner vand. Opløsningen tørres, og opløsningsmidlet afdestilleres i vakuum.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.
5 En organisk mercaptan opløses i et passende opløsningsmiddel, såsom dioxan, isopropylakohol eller lignende. Der tilsættes natriumhydroxidopløsning, og reaktionsblandingen opvarmes. Der tilsættes et aktivt organisk halogenid, og blandingen varmes under tilbagesvaling. Oparbejdningen sker 10 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 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 fremstilling belyses nærmere ved hjælp af de følgende eksempler. Efter fremstillingseksem-15 pierne følger en tabel over forbindelser, som kan fremstilles i overensstemmelse med de beskrevne procedurer. 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 further elucidated by the following examples. Following the preparation examples are a table of compounds which can be prepared in accordance with the procedures described. The compounds have been assigned numbers which are used to identify the compounds for the remainder of the description.
Eksempel 20 Fremstilling af bis-(3,3-dichlorallyl)-sulfid.Example 20 Preparation of bis (3,3-dichloroallyl) sulfide.
1,1,3-trichlorpropen-l (1100 g, 7,5 M) blev opløst i en liter isopropanol, og natriumsulfid, nonahydrat (900 g, 3,75 M), som var blevet pulveriseret groft, blev tilsat i løbet af en time ved 15°C. Blandingen blev omrørt ved 25-25 30°C i 3 timer og ved 50°C i 2 timer. Den fik lov at henstå natten over ved stuetemperatur. Det udfældede natriumchlo= rid 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 30 400 ml portioner vand. Opløsningen blev tørret over magne= siumsulfat, og opløsningsmidlet blev fjernet i vakuum. Det 142932 5 tilbageværende opløsningsmiddel blev fjernet ved ca.0,5 mm Hg. Der opnåedes en rødbrun væske, udbytte 853 g (90%).1,1,3-trichloropropene-1 (1100 g, 7.5 M) was dissolved in one liter of isopropanol and sodium sulfide, nonahydrate (900 g, 3.75 M), which had been coarsely pulverized, was added over for one hour at 15 ° C. The mixture was stirred at 25-25 30 ° C for 3 hours and at 50 ° C for 2 hours. 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 30 400 ml portions of water. The solution was dried over magnesium sulfate and the solvent removed in vacuo. The remaining solvent was removed at about 0.5 mm Hg. A reddish brown liquid was obtained, yield 853 g (90%).
Formlen blev bekræftet ved hjælp af NMR-spektroskopi. Produktet destillerede ved kogepunkt 75-77°C/35 mm Hg.The formula was confirmed by NMR spectroscopy. The product distilled at boiling point 75-77 ° C / 35 mm Hg.
5 Tabel 1.Table 1.
r1-s-r2· Smp.°Cr1-s-r2 · mp ° C
elleror
Forbindelse 9 „30 nr. R~ ET _D_ 1 CC12=CHCH2 CC12=CHCH2 75-77/35 mm Hg 10 2 CH3CC1=CHCH2 CH3CC1=CHCH2 1,5387 3 CHC1=CHCH2 CHC1=CHCH2 1,5270 4 CC12=CC1CH2 CC12=CC1CH2 1,5810 5 C1CH2CH2CH2 CH2CH2CH2C1 1,4528 6 C1-CH=CC1-CII2 CH2CC1=CHC1 rød/brun væske 15 Modgiftforbindelserne blev benyttet i effektive herbicide modgiftpræparater indeholdende substituerede acetanilider i kombination med de ovenfor beskrevne modgiftforbindelser.Compound 9 "30 No. R ~ ET _D_ 1 CC12 = CHCH2 CC12 = CHCH2 75-77 / 35 mm Hg 10 2 CH3CC1 = CHCH2 CH3CC1 = CHCH2 1.5387 3 CHC1 = CHCH2 CHC1 = CHCH2 1.5270 4 CC12 = CC1CH2 CC12 = CC1CH2 1.5810 5 C1CH2CH2CH2 CH2CH2CH2C1 1.4528 6 C1-CH = CC1-CII2 CH2CC1 = CHC1 red / brown liquid The antidote compounds were used in effective herbicidal antidotes containing substituted acetanilides in combination with the antidotes described above.
De blev afprøvet på følgende måde.They were tested as follows.
Procedure: Multiafgrøde-modgiftbeskyttelse.Procedure: Multi-crop antidote protection.
20 Plantekasser blev fyldt med Felton-lerblandet sandjord. En varietet af græs og bredbladede afgrøder blev benyttet til dette forsøg. LASSO ® og den pågældende herbicidmodgift blev nu påført separat ved pipettering af afmålte mængder af de pågældende stamopløsninger til jorden under indfø- 142932 6 ring af denne i en 20 liter roterende cementblander. Stam-opløsningerne blev fremstillet som følger:20 seed boxes were filled with Felton clay-mixed sandy soil. A variety of grass and broadleaf crops were used for this experiment. LASSO ® and the relevant herbicide antidote were now applied separately by pipetting measured amounts of the relevant stock solutions to the soil during introduction into a 20 liter rotary cement mixer. The stock solutions were prepared as follows:
Herbicid-stamopløsning, 2,24 kg/ha: 427 mg LASSO 4E fortyndes med 100 ml deioniseret vand, således at 1 ml svarer til 5 2,05 mg (a.i.) og 4 ml svarer til 8,2 mg, der er ækvivalent med 2,24 kg/ha plantekasse.Herbicide stock solution, 2.24 kg / ha: Dilute 427 mg of LASSO 4E with 100 ml of deionized water so that 1 ml corresponds to 5 2.05 mg (ai) and 4 ml corresponds to 8.2 mg equivalent to 2.24 kg / ha plant box.
Modgift-stamopløsninger fremstilles ved fortynding af 102 mg teknisk materiale med 10 ml acetone med 1% Ttøeen 20® (polyoxyethylensorbitanmonolaurat), så at 2 ml svarer til 10 5,6 kg/ha plantekasse.Antidote stock solutions are prepared by diluting 102 mg of technical material with 10 ml of acetone with 1% Ttoeen 20® (polyoxyethylene sorbitan monolaurate) so that 2 ml corresponds to 10 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 tilsåning. Begyndelsestrinnet ved forberedelsen består i at fjerne ca. 1/2 liter jordprøve fra hver 15 plantekasse med henblik på tilbageholdelse og ahvendelse til tildækning af frøene efter plantning. Derpå udjævnes jorden, og 6 mm dybe furer frembringes i hver plantekasse. Plantekasser, som er behandlet med herbicidet og additivet, tilsås med majs (Zea maize), sukkerroe (Beta vulgare), 20 solsikke (Helianthus annus), bomuld (Gossypium hirsutum), sojabønne (Glycine max) og olieholdig raps (Brassica napus). Plantekasser behandlet med 2,24 kg/ha LASSO tilsås med majs (Zea maize), hvede (Triticum aestivum), ris (Oryza sativa), durra (Sorghum vulgare) og byg (Hordeum vulgare).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 15 plant boxes for retention and use to cover the seeds after planting. The soil is then leveled and 6 mm deep grooves are produced in each plant box. Plant boxes treated with the herbicide and additive were sown with corn (Zea maize), sugar beet (Beta vulgare), 20 sunflowers (Helianthus annus), cotton (Gossypium hirsutum), soybean (Glycine max) and oilseed rape (Brassica napus). Plant boxes treated with 2.24 kg / ha LASSO were sown with maize (Zea maize), wheat (Triticum aestivum), rice (Oryza sativa), sorghum (Sorghum vulgare) and barley (Hordeum vulgare).
25 Frøene tildækkes derpå med den ca. halve liter jordprøve, som er blevet fjernet før såning.The seeds are then covered with the approx. half a liter of soil sample which has been removed before sowing.
Plantekasserne 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 seed boxes are then placed on greenhouse benches where the temperatures are kept between approx. 21 ° C and approx. 32 ° C. The soil is watered by spraying to ensure good plant growth.
30 Beskadigelsesvurderinger foretages 2, 3 eller 4 uger efter, at behandlingerne er udført. Jord behandlet med herbicider - alene i mængder på 0,56, 2,24, 3,36, 5,6 eller 6,72 kg/ha 7 142932 er medtaget for at give en basis for bestemmelse af omfanget af beskadigelsesreduktion, som tilvejebringes ved hjælp af herbicidmodgiften. Den procentiske beskyttelse bestemmes ved en sammenligning med plantekasser, der ikke er behand-5 let med den pågældende modgift, men med herbicidet alene. Resultaterne er opført i tabel 2.30 Damage assessments are made 2, 3 or 4 weeks after the treatments are completed. Soil treated with herbicides - only in amounts of 0.56, 2.24, 3.36, 5.6 or 6.72 kg / ha 7 has been included to provide a basis for determining the extent of damage reduction provided by using the herbicide antidote. The percentage protection is determined by a comparison with plant boxes not treated with the antidote concerned, but with the herbicide alone. The results are listed in Table 2.
Tabel 2.Table 2.
Multiafgrøde-beskyttelsesresultater Procent beskyttelseMulti crop protection results Percent protection
Modgift- Herbicid Modgift % forbindelse mængde mængde beskyttelse nr._ kg/ha kg/ha Afgrøde (4 uger) 1 LASSOC 2,24 5,6 hvede 39 LASSO 2,24 5,6 durra 100 c = 2-chlor-2',6'-diethyl-N-(methoxymethyl)acetanilid.Antidote- Herbicide Antidote% Compound Amount Amount of Protection No._ kg / ha kg / ha Crop (4 weeks) 1 LASSOC 2.24 5.6 Wheat 39 LASSO 2.24 5.6 sorghum 100 c = 2-chloro-2 ' , 6'-diethyl-N- (methoxymethyl) acetanilide.
Endvidere blev følgende afprøvning iværksat med henblik på bedømmelse af forbindelserne nr. 1, nr. 4 og nr. 8 som herbicidmodgifte over for acetanilidherbicider. De benyttede 15 afgrøder var hvede og durrakerner.In addition, the following test was carried out for the purpose of assessing compounds Nos. 1, 4 and 8 as herbicide antidotes to acetanilide herbicides. The 15 crops used were wheat and dried grains.
Modgiftene blev påført ved en 0,5% frøbehandling og ved en overfladebehandling før spiring med 5,6 kg/ha (tankblanding).The antidotes were applied by a 0.5% seed treatment and by a surface treatment before germination at 5.6 kg / ha (tank mixture).
"Dual 6E" og "Antor 4E" blev påført med 3,36 og 4,48 kg/ha ved en overfladebehandling før spiring (tankblanding)."Dual 6E" and "Antor 4E" were applied at 3.36 and 4.48 kg / ha in a surface treatment before germination (tank mix).
20 Modgiftforbindelser;20 Antidotes;
Nr. i ci2=chch2-s-ch2ch=cci2No. in ci2 = chch2-s-ch2ch = cci2
Nr. 3 CH2CH=CHC1-S-CHC1=CHCH2No. 3 CH2CH = CHC1-S-CHC1 = CHCH2
Nr. 6 CHC1=CC1CH2-S-CH2CC1=CHC1 142932 8No. 6 CHC1 = CC1CH2-S-CH2CC1 = CHC1 142932 8
Herbicider: "Dual": /CH3 π / \ /C-CHoCl “\r \ ( ^CH-CH2OCH3 C2H5 CH3 N-(3'-methoxypropyl-(2))-2-methyl-6-ethyl-chloracetanilid.Herbicides: "Dual": / CH 3
"Antor": /C2H5/5-ch2ci \5(“^CH2C0c2H5"Antor": / C2H5 / 5-ch2Cl5 ("^ CH2C0c2H5
Nc2H5 o N-chloracetyl-2,6-diethyl-anilinoaceteddikesyreethylester.Nc2H5 o N-chloroacetyl-2,6-diethyl-anilinoacetacetic acid ethyl ester.
5 De afprøvede afgrøder var hvede (Wh) durrakerner(milo) (Ml)5 The tested crops were wheat (Wh) grains (mil) (Ml)
Ukrudtsarter: Vandgræs (WG) Rævehale (FT) 9 142932 (O o G ,β O O Cso loo \ S TP *P H ID \D t— -Weeds: Watergrass (WG) Fox Tail (FT) 9 142932 (O o G, β O O Cso loo \ S TP * P H ID \ D t— -
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Tdypqco Hen Hen g G rd £Tdypqco Hen Hen g G rd £
21¾¾ H CU 03 Q) H G21¾¾ H CU 03 Q) H G
β -g 00 OP dp ΦίηΉΦβ -g 00 OP dp ΦίηΉΦ
WMlOfN CD fN CD (N J3 C H GWMlOfN CD fN CD (N J3 C H G
s g · \ - X - \ Η φ φ.s g · \ - X - \ Η φ φ.
inHinHUOH G >HinHinHUOH G> H
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Beskyttelsen blev vist for beskadigelse af durra og hvede ved forskellige påføringsmængder. Beskadigelsen skyldes acetanilidherbicider. Der blev benyttet frøbehandling og påføring før spiring (tankblanding).The protection was shown for damage to durra and wheat at different application rates. The damage is caused by acetanilide herbicides. Seed treatment and application before germination (tank mix) was used.
5 Modgiftforbindelserne og præparaterne ifølge opfindelsen kan benyttes i en hvilken som helst passende form. Modgift-forbindelserne kan således indgå i emulgerbare væsker eller koncentrater samt foreligge i form af væsker, befugte-lige pulvere, puddere, granulære masser eller en hvilken 10 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 eller efter plantning af frøene. Det må imidlertid forstås, at herbiciderne kan inkorporeres i jorden, og at mod-15 giftforbindelsen derefter kan inkorporeres i jorden. Selve afgrødefrøene kan endvidere behandles med en ikke-fytotoksisk mængde af forbindelsen og plantes i jorden, som er blevet behandlet med herbicider, eller som er ubehandlet med herbicid og derefter behandles med herbicidet. Tilsæt-20 ningen af modgiftforbindelsen påvirker ikke herbicidernes herbicide virkning.The antidotes and compositions of the invention can be used in any suitable form. The antidotes 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 before or after planting the seeds. However, it is to be understood that the herbicides can be incorporated into the soil and that the antifungal compound 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 the soil which has been treated with herbicides or which has been treated with herbicide and then treated with the herbicide. The addition of the antidote does not affect the herbicidal action of the herbicides.
Mængden af tilstedeværende modgiftforbindelse kan ligge mellem ca. 0,01 og ca. 15 vægtdele modgiftforbindelse som her beskrevet pr. vægtdel herbicid. Den nøjagtige mængde 25 modgiftforbindelse vil sædvanligvis blive bestemt af økonomiske forhold for den meste effektive brugbare mængde.The amount of antidote present may be between about. 0.01 and approx. 15 parts by weight of antidote as described herein. part by weight of herbicide. The exact amount of antidote compound will usually be determined by economic conditions for the most effective usable amount.
Det må forstås, at en ikke-fytotoksisk mængde af modgiftforbindelsen vil blive benyttet i de her beskrevne herbicide materialer.It is to be understood that a non-phytotoxic amount of the antidote will be used in the herbicidal materials described herein.
30 De i tabellerne og andet steds 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 142932 11 inden for det ønskede eller det anbefalede omfang.The herbicides listed in the tables and elsewhere are used in amounts which will produce an effective control of undesirable vegetation. The quantities are within the recommended quantities specified by the supplier. The weed control is therefore in each case commercially acceptable within the desired or recommended range.
Det er klart, at klasserne af her beskrevne og illustrerede herbicide midler er karakteriseret som effektive herbicider, som udviser en sådan aktivitet. Graden af denne herbicide 5 aktivitet varierer mellem bestemte forbindelser og mellem kombinationer af bestemte forbindelser. På lignende måde varierer aktivitetsgraden i et vist omfang blandt arterne af planter, hvortil en bestemt herbicid forbindelse eller herbicid kombination kan anvendes. Udvælgelse af en bestemt 10 herbicid forbindelse eller herbicid kombination til bekæmpelse af uønskede plantearter kan således foretages. Inden for den foreliggende opfindelses rammer kan forhindring af beskadigelse af en bestemt afgrødeart opnås ved tilstedeværelse af en bestemt forbindelse eller kombination. Nytte-15 plantearterne, som kan beskyttes ved hjælp af denne fremgangsmåde, tænkes ikke begrænset til de bestemte afgrøder, som benyttes i eksemplerne.It is to be understood that the classes of herbicides described and illustrated herein are characterized as effective herbicides which exhibit such activity. The degree of this herbicidal activity varies between certain compounds and between combinations of certain compounds. Similarly, the degree of activity varies to some extent among the species of plants to which a particular herbicide compound or herbicide combination may be used. Thus, selection of a particular herbicide compound or herbicide combination to control undesirable plant species can be made. Within the scope of the present invention, prevention of damage to a particular crop species can be achieved by the presence of a particular compound or combination. The utilitarian plant species which can be protected by this method are not intended to be limited to the particular crops used in the examples.
De herbicide forbindelser, som benyttes ved udøvelsen af opfindelsen, er aktive herbicider af en generel type. Det 20 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 plante-25 sted, hvor bekæmpelse ønskes. Præparaterne ifølge opfindelsen indbefatter sådanne, hvori den foretrukne aktive herbicide forbindelse er valgt blandt 2-chlor-2',6'-diethyl-N-(methoxymethyl)acetanilid, 2-chlor-N-isopropylacetanilid og N,N-diallyl-2-chloracetanilid og kombinationer deraf.The 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 controlling 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 preferred active herbicidal compound is selected from 2-chloro-2 ', 6'-diethyl-N- (methoxymethyl) acetanilide, 2-chloro-N-isopropylacetanilide and N, N-diallyl-2 chloroacetanilide and combinations thereof.
30 Med et herbicid som her benyttet menes en forbindelse, som bekæmper eller modificerer væksten af vegetation eller planter. Sådanne bekæmpende eller modificerende virkninger indbefatter alle afvigelser fra naturlig udvikling, såsom f.eks. dræbning, retardering, afbladning, udtørring, regu-By a herbicide as used herein is meant a compound which fights or modifies the growth of vegetation or plants. Such combating or modifying effects include all deviations from natural evolution, such as e.g. killing, retarding, flaking, drying, regulating
Claims (3)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39423073A | 1973-09-04 | 1973-09-04 | |
| US39423073 | 1973-09-04 | ||
| 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. |
| DK462574 | 1974-08-30 | ||
| DK310476 | 1976-07-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK310476A DK310476A (en) | 1976-07-09 |
| DK142932B true DK142932B (en) | 1981-03-02 |
| DK142932C DK142932C (en) | 1981-09-28 |
Family
ID=23558086
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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. |
Country Status (22)
| Country | Link |
|---|---|
| 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) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU195398B (en) * | 1986-06-26 | 1988-05-30 | Eszakmagyar Vegyimuevek | Preparation comprising nitrile derivative antidote alone or with herbicidal active ingredient(s) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
-
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 |
|---|---|
| DE2441741A1 (en) | 1975-03-13 |
| DK310476A (en) | 1976-07-09 |
| NL176738B (en) | 1985-01-02 |
| TR18303A (en) | 1977-01-07 |
| DK141711B (en) | 1980-06-02 |
| 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 |
| 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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