DE2528302A1 - Selective herbicide for beet and soya beans - contg. 3-methyl 4 amino 6 phenyl 1,2,4 triazin 5 one and 4 methoxy benzyl diethyl thiolcarbamate - Google Patents
Selective herbicide for beet and soya beans - contg. 3-methyl 4 amino 6 phenyl 1,2,4 triazin 5 one and 4 methoxy benzyl diethyl thiolcarbamateInfo
- Publication number
- DE2528302A1 DE2528302A1 DE19752528302 DE2528302A DE2528302A1 DE 2528302 A1 DE2528302 A1 DE 2528302A1 DE 19752528302 DE19752528302 DE 19752528302 DE 2528302 A DE2528302 A DE 2528302A DE 2528302 A1 DE2528302 A1 DE 2528302A1
- Authority
- DE
- Germany
- Prior art keywords
- active ingredient
- weeds
- triazin
- methyl
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
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)
Abstract
Description
Mittel zur selektiven Unkrautbekämpfung in Rüben und Sojabohnen Die vorliegende Erfindung betrifft eine neue herbizide Nirkstoffkombinaion, die aus einem bekannten 3-Alkyl-1,2,4-triazin-5-on einerseits und aus einem bekannten Uhiolcarbamat andererseits besteht, und eine besonders gute herbizide ,jirksameit zur selektiven Unkrautbekämpfung in Rüben und Sojabohnen aufweist.Means for selective weed control in beets and soybeans The The present invention relates to a new herbicidal Nirkstoffkombinaion from a known 3-alkyl-1,2,4-triazin-5-one on the one hand and a known Uhiolcarbamat On the other hand, there is, and a particularly good herbicidal, effective for selective Has weed control in beets and soybeans.
Es ist bereits bekannt geworden, daß man 3-Alkyl-112,4-triazin-5-one, z.B. 5-Methyl-4-amino-6-phenyl-1,2,4-triazin-5-on, als selektive Herbizide in Süben verwenden kann (vgl. Deutsche Offenlegungsschrift 2 224 161).It has already become known that 3-alkyl-112,4-triazin-5-ones, e.g. 5-methyl-4-amino-6-phenyl-1,2,4-triazin-5-one, as selective herbicides in Süben can use (see German Offenlegungsschrift 2 224 161).
Es ist weiterhin bekannt, daß man Thiolcarbamate,z.B. S-(p-Methoxybenzyl)-N,N-diäthyl-thiolcarbamat, als Herbizide verwenden kann (vgl. Deutsche Offenlegungsschrift 1 995 892).It is also known that thiol carbamates, e.g. S- (p-methoxybenzyl) -N, N-diethyl thiol carbamate, can use as herbicides (cf. German Offenlegungsschrift 1 995 892).
Bei niedrigen Aufwandmengen und -konzentrationen ist die selektive herbizide Wirksamkeit der vorgenannten Stoffe bei der Unkrautbekämpfung in Rüben jedoch nicht immer ganz befriedigend.At low application rates and concentrations, the selective one herbicidal effectiveness of the aforementioned substances in combating weeds in beets but not always entirely satisfactory.
Es wurde nun gefunden, daß die neue Itirkstoffkombination aus (1) 3-Methyl-4-amino-6-phenyl-1,2,4-triazin-5-on der Formel und (2) S-(p-Methoxybenzyl)-N,N-diäthyl-tniolcarbamat der Formel eine besonders breite und selektive herbizide Wirkung in Rüben-und in Sojabohnenkulturen aufweist.It has now been found that the new active ingredient combination of (1) 3-methyl-4-amino-6-phenyl-1,2,4-triazin-5-one of the formula and (2) S- (p-methoxybenzyl) -N, N-diethyltniolcarbamate of the formula has a particularly broad and selective herbicidal action in beet and soybean crops.
Überraschenderweise ist die Wirksamkeit der erfindungsgemäßen Wirkstoffkombination wesentlich höher als die Summe der Wirkungen der einzelnen Wirkstoffe. Es liegt ein nicht vorhersehbarer echter synergistischer Effekt vor und nicht nur eine Wirkungsergänzung.The effectiveness of the active ingredient combination according to the invention is surprising much higher than the sum of the effects of the individual active ingredients. It lies an unpredictable real synergistic effect before and not just an effect supplement.
Die Wirkstoffkombination stellt somit eine wertvolle Bereicherung der Rübenherbizide und der Herbizide für den Sojabohnenanbau dar.The combination of active ingredients is a valuable asset beet herbicides and herbicides for soybean cultivation.
Die in der erfindungsgemäßen Wirkstoffkombination enthaltenen Wirkstoffe sind bereits bekannt (vgl. Deutsche Offenlegungsschriften 2 224 161 und 1 995 892).The active ingredients contained in the active ingredient combination according to the invention are already known (cf. German Offenlegungsschriften 2 224 161 and 1 995 892).
Der synergistische Effekt zeigt sich besonders stark bei bestimmten Kombinationsverhältnissen. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in der irkstoffkombination in relativ großen Bereichen schwanken. Im allgemeinen entfallen auf 1 Gewichtsteil an Wirkstoff der Formel (I) 0,1 bis 10 Gewichtsteile, vorzugsweise 0,1 bis 5 Gewichtsteile an Wirkstoff der Formel (II).The synergistic effect is particularly strong with certain Combination ratios. However, the weight ratios of the active ingredients in the combination of active ingredients fluctuate in relatively large areas. In general account for 1 part by weight of active ingredient of the formula (I) 0.1 to 10 parts by weight, preferably 0.1 to 5 parts by weight of active ingredient of the formula (II).
Die erfindungsgemäße Wirkstoffkombination zeigt eine sehr gute Wirkung gegen Unkräuter und Ungräser, ohne die Rüben und die Sojabohnen zu schädigen. Sie kann daher zur selektiven Unkrautbekämpfung in Rüben und Sojabohnenkulturen verwendet werden.The active ingredient combination according to the invention shows a very good effect against weeds and grass weeds without damaging the beets and soybeans. she can therefore be used for selective weed control in beet and soybean crops will.
Als Unkräuter kommen insbesondere in Frage: Dikotyle wie Senf (Sinapis), Kresse (Lepidium),Labkraut (Galium),Sternmiere (Stellaria), Kamille (Matricaria),Hundskamille (Anthemis),Knopfkraut Galinsoga),Gänsefuß (Chenopodium),Brennessel (Urtica),Kreuzkraut (Senecio), Fuchsschwanz (Amaranthus), Portulak (Portulaca), Spitzklette (Xanthium), Winde (Convolvulus), Prunkwinde (Ipomoea), Knöterich (Polygonum), Sesbanie (Sesbania), Ambrosie (Ambrosia), Kratzdistel (Cirsium), Distel (Carduus), Gänsedistel (Sonchus), Nachtschatten (Solanum), Sumpfkresse (Rorippa), Rotala, Büchsenkraut (Lindernia), Taubnessel (Lamium), Ehrenpreis (Veronica), Schönmalve (Abutilon), Emex, Stechapfel (Datura), Veilchen (Viola), Hanfnessel, Hohlzahn (Galeopsis), Mohn (Papaver), Flockenblume (Centaurea). Monokotyle wie Huhnerhirse, (Echinochloa),Borstenhirse (Setaria),Hirse (Panicum),Fingerhirse (Digitaria),Lieschgras (Phleum),Rispengras (Poa),Schwingel (Festuca) Eleusine, Brachiaria, Lolch (Lolium), Trespe (Bromus), Hafer (Avena), Zypergras (Cyperus), Mohrenhirse (Sorghum), Quecke (Agropyron), Hundszahngras (Cynodon), Monocharia, Fimbristylis, Pfeilkraut (Sagittaria), Sumpfried (Eleocharis), Simse (Scirpus), Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Straußgras (Agrostis), Fuchsschwanzgras (Alopecurus), Windhalm (Apera).Particularly suitable weeds are: dicots such as mustard (Sinapis), Cress (Lepidium), bedstraw (Galium), chickweed (Stellaria), chamomile (Matricaria), dog chamomile (Anthemis), buttonwort (Galinsoga), goose foot (Chenopodium), nettle (Urtica), ragwort (Senecio), foxtail (Amaranthus), purslane (Portulaca), pointed burdock (Xanthium), Morning glory (Convolvulus), morning glory (Ipomoea), knotweed (Polygonum), sesbania (Sesbania), Ambrosia (Ambrosia), scrub thistle (Cirsium), thistle (Carduus), goose thistle (Sonchus), Nightshade (Solanum), pond cress (Rorippa), Rotala, boxweed (Lindernia), Dead nettle (Lamium), speedwell (Veronica), beautiful mallow (Abutilon), Emex, thorn apple (Datura), violets (Viola), hemp nettle, hollow tooth (Galeopsis), poppy seeds (Papaver), knapweed (Centaurea). Monocots such as chicken millet (Echinochloa), bristle millet (Setaria), millet (Panicum), fingergrass (Digitaria), timothy grass (Phleum), bluegrass (Poa), fescue (Festuca) Eleusine, Brachiaria, Lolch (Lolium), Trespe (Bromus), Oats (Avena), Sedge grass (Cyperus), black millet (sorghum), couch grass (Agropyron), dog tooth grass (Cynodon), Monocharia, fimbristylis, arrowhead (Sagittaria), swamp reed (Eleocharis), ledges (Scirpus), Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, ostrich grass (Agrostis), Foxtail grass (Alopecurus), wind stalk (Apera).
Besonders hervorzuheben ist die gute Wirksamkeit der erfindungsgemäßen Wirkstoffkombination gegen schwer bekämpfbare Ungräser, z. B. Flughafer (Avena fatua) und Fingerhirse (Digitaria sanguinach£), sowie gegen schwer bekämpfbare Unkräuter, z. B. Klettenlabkraut (Galium aparine). Von besonderem Vorteil ist es, daß solche üblicherweise schwer bekämpfbaren Ungräser und Unkräuter mit der erfindungsgemäßen Wirkstoffkombination gleichzeitig bekämpft werden können. Particularly noteworthy is the good effectiveness of the invention Combination of active ingredients against difficult-to-control grass weeds, e.g. B. Wild oats (Avena fatua) and finger millet (Digitaria sanguinach £), as well as against weeds that are difficult to control, z. B. Burdock weed (Galium aparine). It is of particular advantage that such weeds and weeds that are usually difficult to control with the inventive method Combination of active ingredients can be combated at the same time.
Die erfindungsgemäße Wirkstoffkombination kann in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulyer, Pasten und Granulate. Diese werden in bekannter Weise hergestellt, z. B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, Benzol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chloräthylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, Alkohole, wie Butanol oder Glycol sowie deren Äther und Ester, Ketone, wie Aceton, Methyläthylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser; mit verAirssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche FlUssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z. B. Aerosol-Treibgase, wie Dichlordifluormethan oder Trichlorfluormethan; als feste Trägerstoffe: natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit, oder Diatomenerde, und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate; als Emulgiermittel: nichtionogene und anionische Emulgatoren, wie Polyoxyäthylen-Fettsäure-Ester, Polyoxyäthylen-Fettalkohol-Äther, z.B. Alkylaryl-polyglycol-Äther, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel: z. B. Lignin, Sulfitablaugen und Methylcellulose.The active ingredient combination according to the invention can be used in the customary formulations such as solutions, emulsions, suspensions, powders, pastes and granulates. These are made in a known manner, e.g. B. by mixing the active ingredients liquefied pressurized liquids with extenders, i.e. liquid solvents Gases and / or solid carriers, optionally using surface-active substances Agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents Means. In the case of the use of water as an extender, z. B. also organic Solvents can be used as co-solvents. As a liquid solvent are essentially: aromatics, such as xylene, toluene, benzene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, Chlorethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B. petroleum fractions, alcohols such as butanol or glycol and their Ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or Cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water; with diluted gaseous extenders or carriers Such liquids are meant which are at normal temperature and under normal pressure are gaseous, e.g. B. aerosol propellants such as dichlorodifluoromethane or trichlorofluoromethane; as solid carrier materials: natural rock flour, such as kaolins, clays, talc, Chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth, and synthetic rock flour, such as finely divided silica, aluminum oxide and silicates; as emulsifier: non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and Protein hydrolysates; as a dispersant: e.g. B. lignin, sulphite waste liquors and methyl cellulose.
Die erfindungsgemäße Wirkstoffkombination kann in den Formulierungen in Mischung mit anderen bekannten Wirkstoffen vorliegen.The active ingredient combination according to the invention can be used in the formulations present in a mixture with other known active ingredients.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90.The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90.
Die Wirkstoffkombination kann als solche, in Form ihrer Formulierungen oder der daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Emulsionen, Schäume, Suspensionen, Pulver, Pasten und Granulate, angewendet werden. Die Anwendung geschieht in üblicher Weise, z. B. durch Verstäuben, Versprühen, Verspritzen, Gießen und Verstreuen.The active ingredient combination can be used as such, in the form of their formulations or the application forms prepared therefrom, such as ready-to-use solutions, emulsions, Foams, suspensions, powders, pastes and granules. The application happens in the usual way, for. B. by dusting, atomizing, spraying, pouring and scatter.
Die Aufwandmengen der erfindungsgemäßen Wirkstoffkombination können in einem gewissen Bereich variiert werden. Im allgemeinen liegen sie zwischen 0,1 und 10 kg/ha, vorzugsweise zwischen 1 und 10 kg/ha.The application rates of the active ingredient combination according to the invention can can be varied within a certain range. Generally they are between 0.1 and 10 kg / ha, preferably between 1 and 10 kg / ha.
Die Anwendung der erfindungsgemäßen Wirkstoffkombination kann vor und/oder nach dem Auflaufen der Pflanzen erfolgen.The application of the active ingredient combination according to the invention can before and / or after the plants emerge.
Die gute herbizide Wirkung der Wirkstoffkombination geht aus den nachfol,enden Beispielen hervor. Während die einzelnen Wirkstoffe in der herbiziden Wirkung Schwächen aufweisen, zeigt die Kombination eine sehr breite Unkrautwirkung, die über eine einfache Wirkungssllmmierung hinausgeht.The good herbicidal effect of the combination of active ingredients comes from the following ends Examples. While the individual active ingredients weaken the herbicidal effect have, the combination shows a very broad weed effect that over a simple effect isolation goes beyond.
Ein synergistischer Effekt liegt bei Herbiziden immer dann vor, wenn die herbizide Wirkung der Wirkstoffkombination größer ist als die der einzeln applizierten Wirkstoffe.With herbicides there is always a synergistic effect when the herbicidal effect of the active ingredient combination is greater than that of the individually applied Active ingredients.
Die zu erwartende Wirkung für eine gegebene Kombination zweier Herbizide kann (vgl. Colby, S. R., "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, Seiten 20-22, 1967) wie folgt berechnet werden: Wenn X = % Schädigung durch Herbizid A bei p kg/ha Aufwandmenge und Y = % Schädigung durch Herbizid B bei q kg/ha Aufwandmenge und E = die erwartete Schädigung der Herbizide A u. B bei p und q kg/ha Aufwandmenge, dann ist E = X + Y - X. .The expected effect for a given combination of two herbicides can (cf. Colby, S. R., "Calculating synergistic and antagonistic responses of herbicide combinations ", Weeds 15, pages 20-22, 1967) can be calculated as follows: If X =% damage by herbicide A at p kg / ha application rate and Y =% damage by herbicide B at q kg / ha application rate and E = the expected damage to the herbicides A and B at p and q kg / ha application rate, then E = X + Y - X..
100 Ist die tatsächliche Schädigung größer als berechnet, so ist die Kombination in ihrer Wirkung überadditiv, d.h. es liegt ein synergistischer Effekt vor. 100 If the actual damage is greater than calculated, then the combination is superadditive in its effect, i.e. it is a synergistic one Effect before.
Aus den Tabelbnder Beispiele A und B geht eindeutig hervor, daß die gefundene herbizide Wirkung der erfindungsgemäßen Wirkstoffkombination bei den Unkräutern größer ist als die berechnete, d.h. es liegt ein echter synergistischer Effekt vor.From the tables of Examples A and B it is clear that the Herbicidal activity found of the active compound combination according to the invention on weeds is greater than the calculated one, i.e. there is a real synergistic effect.
Beispiel A Pre-emergence-Test Lösungsmittel: 5 Gewichtsteile Aceton Emulgator: 1 Gewichtsteil Alkylarylpolyglycoläther Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.Example A Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether Active ingredient preparation is mixed 1 part by weight of active ingredient with the specified Amount of solvent, add the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.
Samen der Testpflanzen werden in normalen Boden ausgesät und nach 24 Stunden mit der Wirkstoffzubereitung begossen.Seeds of the test plants are sown in normal soil and after Doused with the active ingredient preparation for 24 hours.
Dabei hält man die Wassermenge pro Flächeneinheit zweckmäßigerweise
konstant. Die Wirkstoffkonzentration in der Zubereitung spielt keine Rolle, entscheidend
ist nur die Aufwandmenge des Wirkstoffs pro Flächeneinheit. Nach drei Wochen wird
der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung
der unbehandelten Kontrolle. Es bedeuten: 0 ffi = keine Wirkung (wie unbehandelte
Kontrolle) 100 6 = totale Vernichtung Wirkstoffe, Aufwandmengen und Resultate gehen
aus der nachfolgenden Tabelle hervor:
Tabelle A pre-emergence-Test
Mit der Wirkstoffzubereitung spritzt man Testpflanzen, welche eine Höhe von 5 - 15 cm haben so, daß die in der Tabelle angegebenen Wirkstoffmengen pro Flächeneinheit ausgebracht werden. Die Konzentration der Spritzbrühe wird so gewählt, daß in 2000 1 Wasser/ha die in der Tabelle angegebenen Wirkstoffmengen ausgebracht werden.Test plants which have a Height of 5-15 cm have such that the amounts of active ingredient given in the table can be applied per unit area. The concentration of the spray liquor will be like this chosen that the amounts of active ingredient given in the table in 2000 1 water / ha be applied.
Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in
6 Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle. Es bedeuten:
O 6 = keine Wirkung (wie unbehandelte Kontrolle) 100 6 = totale Vernichtung Wirkstoffe,
Aufwandmengen und Resultate gehen aus der nachfolgenden Tabelle hervor:
Tabelle
B post-emergence-Test
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752528302 DE2528302A1 (en) | 1975-06-25 | 1975-06-25 | Selective herbicide for beet and soya beans - contg. 3-methyl 4 amino 6 phenyl 1,2,4 triazin 5 one and 4 methoxy benzyl diethyl thiolcarbamate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752528302 DE2528302A1 (en) | 1975-06-25 | 1975-06-25 | Selective herbicide for beet and soya beans - contg. 3-methyl 4 amino 6 phenyl 1,2,4 triazin 5 one and 4 methoxy benzyl diethyl thiolcarbamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2528302A1 true DE2528302A1 (en) | 1977-01-13 |
Family
ID=5949921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752528302 Pending DE2528302A1 (en) | 1975-06-25 | 1975-06-25 | Selective herbicide for beet and soya beans - contg. 3-methyl 4 amino 6 phenyl 1,2,4 triazin 5 one and 4 methoxy benzyl diethyl thiolcarbamate |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2528302A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2477837A1 (en) * | 1980-02-22 | 1981-09-18 | Kumiai Chemical Industry Co | HERBICIDE COMPOSITION BASED ON 4-AMINO-3-METHYL-6-PHENYL-1,2,4-TRIAZINE-5- (4H) ONE THIOCARBAMATE DERIVATIVE AND THE APPLICATION OF THIS COMPOSITION TO THE DESTRUCTION OF UNDESIRABLE PLANTS |
| US4392883A (en) * | 1981-02-23 | 1983-07-12 | Kumiai Chemical Industry Co. Ltd. | Herbicidal composition and process |
| EP4295686A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
| EP4295687A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
| EP4295684A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
| EP4295685A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Method of application of herbicidal active ingredients in different stages |
-
1975
- 1975-06-25 DE DE19752528302 patent/DE2528302A1/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2477837A1 (en) * | 1980-02-22 | 1981-09-18 | Kumiai Chemical Industry Co | HERBICIDE COMPOSITION BASED ON 4-AMINO-3-METHYL-6-PHENYL-1,2,4-TRIAZINE-5- (4H) ONE THIOCARBAMATE DERIVATIVE AND THE APPLICATION OF THIS COMPOSITION TO THE DESTRUCTION OF UNDESIRABLE PLANTS |
| DE3106407A1 (en) * | 1980-02-22 | 1982-02-11 | Kumiai Chemical Industry Co., Ltd., Tokyo | HERBICIDAL AGENT AND METHOD FOR INHIBITING GROWTH OF UNWANTED PLANTS |
| US4392883A (en) * | 1981-02-23 | 1983-07-12 | Kumiai Chemical Industry Co. Ltd. | Herbicidal composition and process |
| EP4295686A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
| EP4295687A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
| EP4295684A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
| EP4295685A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Method of application of herbicidal active ingredients in different stages |
| WO2023248223A1 (en) * | 2022-06-22 | 2023-12-28 | Adama Agan Ltd. | Method of application of herbicidal active ingredients in different stages |
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