DE1911527A1 - Herbicidal triazine compounds - Google Patents

Herbicidal triazine compounds

Info

Publication number
DE1911527A1
DE1911527A1 DE19691911527 DE1911527A DE1911527A1 DE 1911527 A1 DE1911527 A1 DE 1911527A1 DE 19691911527 DE19691911527 DE 19691911527 DE 1911527 A DE1911527 A DE 1911527A DE 1911527 A1 DE1911527 A1 DE 1911527A1
Authority
DE
Germany
Prior art keywords
triazine
group
weight
parts
methylthioethyl
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
Application number
DE19691911527
Other languages
German (de)
Inventor
Fischer Dr Adolf
Maschke Dr Artur
Koenig Dr Karl-Heinz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE19691911527 priority Critical patent/DE1911527A1/en
Publication of DE1911527A1 publication Critical patent/DE1911527A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
    • 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
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/48—Two nitrogen atoms
    • C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/48—Two nitrogen atoms
    • C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06F—LAUNDERING, DRYING, IRONING, PRESSING OR FOLDING TEXTILE ARTICLES
    • D06F71/00—Apparatus for hot-pressing clothes, linen or other textile articles, i.e. wherein there is substantially no relative movement between pressing element and article while pressure is being applied to the article; Similar machines for cold-pressing clothes, linen or other textile articles
    • D06F71/02—Apparatus for hot-pressing clothes, linen or other textile articles, i.e. wherein there is substantially no relative movement between pressing element and article while pressure is being applied to the article; Similar machines for cold-pressing clothes, linen or other textile articles actuated wholly by hand or foot

Abstract

Title cpds of the general formula (in which R1 = Cl, Br, CN, OCH3 or SCH3 gp, R2 is an 5-7 C alkoxyalkyl gp, a lower alkylthioisopropy gp or an ethylthioethyl gp, and R3 is an 4-7 C alkoxy alkyl gp, a lower alkyl gp or a 3-5C alkylthioalkyl gp; with the proviso that if R3 is a methylthioethyl gp R2 is an additional methylthioethyl gp) are prepared by the interaction of cncl or CNBr with amines in the presence of an acid acceptor. Exchange of the three halogen atoms in the triazine molecule can follow by reaction with NaOMe, NaSMe or NaCN. Title cpds are effective herbicides in the cultivation of cereal crops.

Description

Triazinderivate Die Erfindung betrifft neue wertvolle Triazinderivate und diese enthaltende Herbizide. Triazine derivatives The invention relates to new valuable triazine derivatives and herbicides containing them.

Es ist bekannt, 2,4,6-substituierte Triazine, insbesondere das 2-Chlor-4,6-bis-(Sthylamino)-s-triazin, als herbizide Wirkstoffe zu verwenden (deutsche Auslegeschrift 1 011 904). Ibz'e Wirkungen befriedigen jedoch nicht.It is known to use 2,4,6-substituted triazines, in particular 2-chloro-4,6-bis (sthylamino) -s-triazine, to be used as herbicidal active ingredients (German Auslegeschrift 1 011 904). Ibz'e However, the effects are not satisfactory.

Es wurde gefunden, daß 2,4,6-substituierte Triazine der allgemeinen Formel in der R1 ein Chlor- oder Bromatom, eine Cyan-, Methoxy- oder Thiomethylgruppe, R2 einen Alkoxyalkylrest mit 5 bis 7 Kohlenstoffatomen, einen niederen Alkylthioisopropylrest, einen Äthylthioäthylrest und R3 einen Alkoxyalkylrest mit 4 bis 7 Kohlenstoffatomen, einen niederen Alkylrest oder einen Alkylthioalkylrest mit 3 bis 5 Kohlenstoffatomen bedeuten, mit der Maßgabe, daß R2 zusätzlich einen Methylthioäthylrest bedeutet, wenn R3 einen Methylthioäthylrest bedeutet, sich gegenüber den bekannten Verbindungen durch eine bessere Kulturpflanzenverträglichkeit bzw. stärkere herbizide Wirkung auszeichnen.It has been found that 2,4,6-substituted triazines of the general formula in which R1 is a chlorine or bromine atom, a cyano, methoxy or thiomethyl group, R2 is an alkoxyalkyl group with 5 to 7 carbon atoms, a lower alkylthioisopropyl group, an ethylthioethyl group and R3 is an alkoxyalkyl group with 4 to 7 carbon atoms, a lower alkyl group or an alkylthioalkyl group 3 to 5 carbon atoms, with the proviso that R2 also denotes a methylthioethyl radical, when R3 denotes a methylthioethyl radical, are distinguished from the known compounds by better crop plant tolerance and stronger herbicidal action.

Diese substituierten Triazine sind bisher in der Literatur nicht beschrieben worden.These substituted triazines have not yet been described in the literature been.

Die Verbindungen können z.B. durch Umsetzung von Cyanurchlorid oder -bromid mit den entsprechenden Aminen in Gegenwart von halogenwasserstdffbindenen Mitteln stufenweise - bei verschiedenen Temperaturen - hergestellt werden. Der gegebenenfalls erwünschte Austausch des dritten Halogenatoms im Triazin kann z.B. durch Reaktion mit Natriummethylat, -methylmercaptid oder -cyanid erfolgen.The compounds can, for example, by reaction of cyanuric chloride or bromide with the corresponding amines in the presence of hydrogen halide bonds Means be produced in stages - at different temperatures. The possibly Desired replacement of the third halogen atom in the triazine can, for example, by reaction with sodium methylate, methyl mercaptide or cyanide.

189 Gewichtsteile Cyanurchlorid werden in 600 Gewichtsteilen Aceton gelöst und bei einer Temperatur von -10; bis 200C tropfenweise mit 90 Gewichtsteilen ethylamin versetzt. Anschließend rührt man das Reaktionsgemisch noch eine Stunde bei -10 bis -200C, saugt das ausgefallene Athylaminhydrochlorid ab und befreit das Filtrat im Vakuum vom Lösungsmittel. Der kristalline Rückstand wird aus Cyclohexan umkristallisiert. Man erhält 189 Gewichtsteile 2,4-Dichlor-6-Sthyl-amino-1,3,5-triazin; Fp. 103 bis 1050C.189 parts by weight of cyanuric chloride are in 600 parts by weight of acetone dissolved and at a temperature of -10; up to 200C dropwise with 90 parts by weight ethylamine added. The reaction mixture is then stirred for a further hour at -10 to -200C, the precipitated ethylamine hydrochloride sucks off and frees it The filtrate was removed from the solvent in vacuo. The crystalline residue is made from cyclohexane recrystallized. 189 parts by weight of 2,4-dichloro-6-ethylamino-1,3,5-triazine are obtained; M.p. 103-1050C.

2-('{-methoxypropylamino)-4-(X-methyl-ß-methylthioSthylamino)-6-thiomethyl-s-triazin: 33,6 Gewichtsteile 2-(γ-methoxypropylamino)-4-(α-methyl-ß-thiomethylAthylamino)-6-chlor-s-triazin werden in 160 Gewichtsteilen Methanol gelöst, 14 Gewichtsteile Triäthylamin zugegeben und dann 8,7 Gewichtsteile Methylmercaptan (gekühlt) eingetropft. Nach Rühren bei Raumtemperatur erhitzt man noch 1 bis 2 Stunden auf 40 bis 500C, verdünnt mit Wasser, schüttelt das Endprodukt mit Methylenchlorid aus, engt die Lösung im Vakuum ein und destilliert: Kpg 217 bis 2180C.2 - ('{- methoxypropylamino) -4- (X-methyl-ß-methylthioSthylamino) -6-thiomethyl-s-triazine: 33.6 parts by weight of 2- (γ-methoxypropylamino) -4- (α-methyl-ß-thiomethyl-ethylamino) -6-chloro-s-triazine are dissolved in 160 parts by weight of methanol, 14 parts by weight of triethylamine are added and then 8.7 parts by weight of methyl mercaptan (cooled) were added dropwise. After stirring at Room temperature is heated for another 1 to 2 hours to 40 to 500C, diluted with water, shakes the end product with methylene chloride, the solution is concentrated in vacuo and distilled: Kpg 217 to 2180C.

2-Methylamino-4-(α-methyl-ß-äthylthioäthyl>-6-chlor-s-triazin: 21,5 Gewichtateile 2-Methylamino-4 ,6-dichlor-s-triazin werden in 200 Gewichtsteilen Essigester gelöst und bei Raumtemperatur - aus zwei Tropfrichtern gleichzeitig - mit 14,3 Gewichtsteilen «-Methylß-&thylthioäthylamin und 4,8 Gewichtsteilen Atßnatron in 15 Gewichtsteilen Wasser versetzt, über Nacht nachgerUhrt, mit Wasser zersetzt, der Niederschlag abgesaugt und die Essigesterphase eingeent. Umkrist.2-methylamino-4- (α-methyl-ß-ethylthioethyl> -6-chloro-s-triazine: 21.5 parts by weight of 2-methylamino-4, 6-dichloro-s-triazine are in 200 parts by weight Ethyl acetate dissolved and at room temperature - from two dropping funnels at the same time - with 14.3 parts by weight of methyl β- & thylthioethylamine and 4.8 parts by weight Sodium hydroxide in 15 parts by weight of water is added, the mixture is stirred overnight, with water decomposed, the precipitate sucked off and the ethyl acetate phase concentrated. Recryst.

aus Petroläther/Aceton; Fp 120 bis 121°C.from petroleum ether / acetone; Mp 120 to 121 ° C.

2-Isopropylamino-4-(«-methyl-ß-n-propoxyäthylamino)-6-thiomethyls-triazin: 28,15 Gewichtsteile 2-Isopropylamino-4-(α-methyl-ß-n-propoxyäthylamino)-6-chlor-s-triazin werden - gelöst in 150 Gewichtsteilen Methanol - mit 12,5 Gewichtsteilen Triäthylami?1 versetzt und in ca. 2 bis .3 Stunden 7,9 Gewichtsteilen Methylmercaptan (50C) (gekühlt) zugetropSt. Man rührt zunächst bei Raumtemperatur, dann 1 bis 2 Stunden bei 40 bis 500C nach, zerlegt mit Wasser, rührt mit Methylchlorid aus, trocknet, engt ein und destilliert: Kp0,4 175 bis 176°C Nachfolgende seien einige der erfindungsgemäßen Wirkstoffe angeführt: R1 R2 R3 Fp Kp Cl NH-CHY" NH-CH2-CH2-S-CH3 65- nu -O-C2Ht; LL '0 I Cl NH-NH-C,II, CH2-0-C2H5 NH-C21{5 2 5 Cl NH-CH 3 NH-C < 3 sCH2-0-C2H5 H2-0-C2H5 C1 NH-CH 3 NH-CH3 97-98 NH-CH N}1-CH oCH2-0-C2H5 3 2 Cl NH-CS 3 NH-CH-CH-CH-0-CH oCH2-0-C2H5 2223 Cl NI-CH 3 NH-CH 3 88-89° XCH2-0-C3H7 Ii 2 37 3 /CH Cl NH-CH 3 NH-C2H 63-66° 2 3' 5 .6366O 3 NH-CH/CH3 NH-CH Kp0,2 162166O H2-0-C 2H5 3 R1 R2 R3 Fp Kp CH -S- NH-CC J NH-CHs 3 K 2 186-187° 3 - CH2-0-C2H5 CH2-0-C2H5 Cl NH-CH2-CH2-S-C2H5 NH-CHX 3 64-66° CH NH-C CH2-0-CH3 CH,-O- NH-CH/ Kp0>1 158-161° CH2-0-C 3H7 ,1 CH -0- NH-CHo 3 CH3 < 3 \CH20-C,H, CH, Kp13 178-184 1. CH3-S- NH-CH\ H2 ° NH-C 2H5 4 182-184° 37 CH -S- NH-CH NH-CHX 3 Kp4 4 175-176° CH2-0 -C3H7 CH3 0> 0 Cl NH-CH2-CH2- S-CH3 NH-CH2-CH2-S-CH3 200-201 Cl NH-C3 3 NH-CH2-CH2-S-C2H5 38-39° \GE2-Q«;53H7 Cl NH-CH2-CH2-S-C2H5 NH-CH2-CH2-S-C2H5 194-195° Cl NH-C2H5 NHCH2CH3 108-109° sCH2 -S-C2H5 Cl NH-CH3 NH CHX 120121O NH-C 3 CH2-S-C2H5 Cli C1 nu cH>CH3 NH-CH- 3 88-89° CH3 sCH2-S-C2H Cl NH-C2H5 NHCHCH3 I 120-123° 5 CH2-S-CH3 Cl NH-CH3 NH-CHs 120-121° CH2-S-C2H5 R1 R2 R3 Fp Kp H3 C1 NH-CH- / NH-CHs H3 CH2-S-CH3 C1 NH-CH2-CH2-CH2 -O-CH3 NHCH$CH3 59-620 CH2-S-C2H5 Cli C1 NH-CH,-CH,-CH,-O-CH, NH-CH<. 2 2 2 3 66-710 CH-S-Cli3 C1 NH-CH,-CH,-CH,-O-CH, NH-CH ' , LCL CH2.-O-C2H, CH3-S- NH-CH2-CH2-$-C2H5 NH-CH2-CH2-S-C2H5 Kpu,2 245-247° Die neuen Verbindungen können als Herbizide in Form von Lösungen, Emulsionen, Suspensionen oder Stäubemittel angewendet werden. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollen in jedem Fall eine feine Verteilung der wirksamen Substanz gewährleisten.2-Isopropylamino-4 - («- methyl-ß-n-propoxyethylamino) -6-thiomethyls-triazine: 28.15 parts by weight of 2-isopropylamino-4- (α-methyl-ß-n-propoxyethylamino) -6-chloro 12.5 parts by weight of triethylamine 1 are added to s-triazine - dissolved in 150 parts by weight of methanol - and 7.9 parts by weight of methyl mercaptan (50C) (cooled) are added dropwise in about 2 to 3 hours. The mixture is initially stirred at room temperature, then for 1 to 2 hours at 40 to 50 ° C., decomposed with water, stirred with methyl chloride, dried, concentrated and distilled: B.p. 0.4 175 to 176 ° C. Some of the active ingredients according to the invention are listed below: R1 R2 R3 Fp Kp Cl NH-CHY "NH-CH2-CH2-S-CH3 65- nu -O-C2Ht; LL '0 I. Cl NH-NH-C, II, CH2-0-C2H5 NH-C21 {5 2 5 Cl NH-CH 3 NH-C <3 sCH2-0-C2H5 H2-0-C2H5 C1 NH-CH3 NH-CH3 97-98 NH-CH N} 1-CH oCH2-0-C2H5 3 2 Cl NH-CS 3 NH-CH-CH-CH-O-CH oCH2-0-C2H5 2223 Cl NI-CH3 NH-CH3 88-89 ° XCH2-0-C3H7 II 2 37 3 / CH Cl NH-CH 3 NH-C2H 63-66 ° 2 3 '5 .6366O 3 NH-CH / CH3 NH-CH bp 0.2 162166O H2-0-C 2H5 3 R1 R2 R3 Fp Kp CH -S- NH-CC J NH-CHs 3 K 2 186-187 ° 3 - CH2-0-C2H5 CH2-0-C2H5 Cl NH-CH2-CH2-S-C2H5 NH-CHX 3 64-66 ° CH NH-C CH2-0-CH3 CH, -O-NH-CH / bp> 1158-161 ° CH2-0-C 3H7, 1 CH -0- NH-CHo 3 CH3 <3 \ CH20-C, H, CH, bp13 178-184 1. CH3-S-NH-CH \ H2 ° NH-C 2H5 4 182-184 ° 37 CH -S- NH-CH NH-CHX 3 bp 4 4 175-176 ° CH2-0 -C3H7 CH3 0> 0 Cl NH-CH2-CH2- S-CH3 NH-CH2-CH2-S-CH3 200-201 Cl NH-C3 3 NH-CH2-CH2-S-C2H5 38-39 ° \ GE2-Q «; 53H7 Cl NH-CH2-CH2-S-C2H5 NH-CH2-CH2-S-C2H5 194-195 ° Cl NH-C2H5 NHCH2CH3 108-109 ° sCH2 -S-C2H5 Cl NH-CH3 NH CHX 1201210 NH-C 3 CH2-S-C2H5 Cli C1 nu cH> CH3 NH-CH- 3 88-89 ° CH3 sCH2-S-C2H Cl NH-C2H5 NHCHCH3 I 120-123 ° 5 CH2-S-CH3 Cl NH-CH3 NH-CHs 120-121 ° CH2-S-C2H5 R1 R2 R3 Fp Kp H3 C1 NH-CH- / NH-CHs H3 CH2-S-CH3 C1 NH-CH2-CH2-CH2 -O-CH3 NHCH $ CH3 59-620 CH2-S-C2H5 Cli C1 NH-CH, -CH, -CH, -O-CH, NH-CH <. 2 2 2 3 66-710 CH-S-Cli3 C1 NH-CH, -CH, -CH, -O-CH, NH-CH ', LCL CH2.-O-C2H, CH3-S-NH-CH2-CH2 - $ - C2H5 NH-CH2-CH2-S-C2H5 Kpu, 2 245-247 ° The new compounds can be used as herbicides in the form of solutions, emulsions, suspensions or dusts. The forms of application depend entirely on the intended use; they should ensure a fine distribution of the active substance in each case.

Zur Herstellung von direkt versprühbaren Lösungen kommen Mineral-81fraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselobl, ferner Kohlenteeröle sowie öle pflanzlich oder tierisehen Ursprungs, außerdem cyclischen Kohlenwasserstoffe, wie Tetrahydronaphthalin, und alkylierte Naphthaline in Betracht.Mineral fractions are used to produce solutions that can be sprayed directly with a medium to high boiling point, such as kerosene or diesel oil, and coal tar oils as well as oils of vegetable or animal origin, as well as cyclic hydrocarbons, such as tetrahydronaphthalene, and alkylated naphthalenes.

Wäßrige Anwendungsformen kennen aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulvern) durch Zusatz von Wasser bersitet werden. Zur Herstellung von Emulsionen können die Substanzen als solche oder in einem Lösungsmittel gelöst mittels Netz- oder Dispergiermitteln in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz Emulgier- oder Dispergiermittel, z.B. Äthylenoxidanlagerungsprodukte, und eventuell Lösungsmittel bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms are known from emulsion concentrates and pastes or wettable powders (wettable powders) by adding water. To produce emulsions, the substances can be used as such or in a solvent dissolved in water by means of wetting or dispersing agents. It can but also emulsifying or dispersing agents from active substances, e.g. Ethylene oxide addition products, and possibly solvent-based concentrates which are suitable for dilution with water.

Stäubemittel können durch Mischen oder gemeinsames Vermahlen der wirksamen Substanzen mit einem festen Trägerstoff, z.B. Ton, Kieselgur, Düngemittel, Talkum, hergestellt werden.Dusts can be created by mixing or grinding together the effective Substances with a solid carrier, e.g. clay, diatomite, fertilizers, talc, getting produced.

Die nachfolgenden Beispiele zeigen die Anwendung der neuen Verbindungen.The following examples show the application of the new compounds.

Beispiel 1 In Versuchstöpfe wurde lehmiger Sandboden eingefüllt und Samen von Mais (Zea mays), Gerste (Hordeum vulgare), Weizen (Triticum sativum), einjAhrigem Rispengras (Poa annua), Ackerfuchsschwanz Alopecurus mvosuroides), weißem Gänsefuß (Chenopodium album), kleine Brennessel (Urtica urens), Ackersenf (Sinapis arvensis), Wicke (Vicia sp.), Kamille (Matricaria chamomilla), Vogelmiere (Stellaria media) eingesät und der Boden danach mit 2-Äthylamino-4-propoxyisopropylamino-6-chlor-3-triazin A, 2-Isopropylamino-4-propoxyisopropylamino-6-chlor-s-triazin B, 2-Isopropylamino-4-propoxy-isopropylamino-6-methoxy-s-triazin' C, 2-Äthylamino-4-propoxyisopropylamino-6-methoxy-s-triazin D, 2, 4-Bis- (äthoxyisopropylamino ) -6-methylmercapto-s-triazin E, 2-Äthylamino-4-äthylthioisopropylamino-6-chlor-s-triazin F und zum Vergleich mit 2-Chlor-4,6-bis-(äthylamino)-s-triazin G mit je 1,5 kg Wirkstoff je ha dispergiert in 500 Litter Wasser je ha behandelt. Nach 4 bis 5 Wochen wurde das in nachfolgender Tabelle aufgeführte Ergebnis erhalten: Wirkstoff A B C D E F G Mais 0-w . 0-10 0 0 Ö-1O 0-10 20-30 Gerste 10 0-10 0-10 0-10 0-10 0-10 20 Weizen 10 0-10 0-10 10 0-10 0-10 0-10 einj. Rispengras 80-90 80 80 80 80 80 80 Ackerfuohsschwanz 80 80 80 70-80 70-80 70-80 70 kl. Brennessel 90-100 90-100 90-100 90-100 90-100 90-100 90-100 Wirkstoff A B C D E F G Ackersenf 100 90-100 90-100 90-100 90 90 90 w. Gänsefuß 90-100 90-100 90-100 90 90 90 80-90 Wicke 90 80-go 80 80 80 80 - 80 Kamille 90 80-90 80-90 80 80 80 80-90; Vogelmiere 100 90-100 90 90 80-go 90 8Q-90 0 = keine Schädigung 100 = totale Schädigung Beispiel 2 Im Gewächshaus wurden die Pflanzen Gerste (Hodeum vulgare), Weizen (Triticum sativum), Mais (Zea mays), kleine Brennessel (Urtica urens), weißer Gänsefuß (Chenopodium album), Kamille (Matricaria chamomilla), Vogelmiere (Stellaria media), einjähriges Rispengras (Poa annua), Ackerfuchsschwanz (Alopecurus myosuroides) bei einer Wuchshöhe von 2,5 - 16 cm mit 2-Athylamino-4-propoxyisopropylamino-6-chlor-s-triazin A, 2-Isopropylamino-4-propoxyisopropylamino-6-chlor-s-triazin. B, 2-Isopro3ylamino-4-propoxyisopropylamino-6-methoxy-s-triazin C, 2,4-Bis- (äthoxyisopropylamino) -6-methylmercaptos-triazin D und zum Vergleich mit 2-Chlor-4,6-bis-<äthylamino)-striazin behandelt. Die Aufwandmenge betrug jeweils 1,5 kg Wirkstoff je ha, dispergiert in 500 Liter Wasser. Nach 3 Wochen wurde das in nachfolgender Tabelle aufgeführte Ergebnis erhalten: Wirkstoff A B C D Gerste 10 0-10 0-10 0-10 20-30 Weizen 0-10 0-10 0-10 0-10 20-30 Mais 10 0 10-20 10 0-10 kl. Brenneseel 90-100 90-100 90-100 90-100 90-100 w. Gänsefuß 90-100 90-100 90-100 90-100 90-100 Kamille 90-100 90-100 90-100 90-100 80-90 Vogelmiere 100 90-100 90-100 90-100 90 einj. Rispengras 90-100 90-100 100 90-100 90 Ackerfuchsschwanz 90-100 90-100 90-100 90-100 80 0 = keine Schädigung 100 = totale Schädigung Example 1 Loamy sandy soil was poured into test pots and Corn seeds (Zea mays), barley (Hordeum vulgare), wheat (Triticum sativum), annual bluegrass (Poa annua), black foxtail Alopecurus mvosuroides), white Goosefoot (Chenopodium album), small nettle (Urtica urens), field mustard (Sinapis arvensis), vetch (Vicia sp.), chamomile (Matricaria chamomilla), chickweed (Stellaria media) and then sown the soil with 2-ethylamino-4-propoxyisopropylamino-6-chloro-3-triazine A, 2-isopropylamino-4-propoxyisopropylamino-6-chloro-s-triazine B, 2-isopropylamino-4-propoxy-isopropylamino-6-methoxy-s-triazine ' C, 2-Ethylamino-4-propoxyisopropylamino-6-methoxy-s-triazine D, 2,4-bis (ethoxyisopropylamino ) -6-methylmercapto-s-triazine E, 2-ethylamino-4-ethylthioisopropylamino-6-chloro-s-triazine F and for comparison with 2-chloro-4,6-bis (äthylamino) -s-triazine G with 1.5 kg of active ingredient each per hectare dispersed in 500 liters of water per hectare treated. After 4 to 5 weeks it was the result listed in the table below was obtained: Active ingredient A B C D E F G corn 0-w. 0-10 0 0 Ö-1O 0-10 20-30 barley 10 0-10 0-10 0-10 0-10 0-10 20 wheat 10 0-10 0-10 10 0-10 0-10 0-10 adj. Bluegrass 80-90 80 80 80 80 80 80 Common foottail 80 80 80 70-80 70-80 70-80 70 small. Nettle 90-100 90-100 90-100 90-100 90-100 90-100 90-100 Active ingredient A B C D E F G field mustard 100 90-100 90-100 90-100 90 90 90 w. Goose foot 90-100 90-100 90-100 90 90 90 80-90 vetch 90 80-go 80 80 80 80 - 80 chamomile 90 80-90 80-90 80 80 80 80-90; Chickweed 100 90-100 90 90 80-go 90 8Q-90 0 = no damage 100 = total damage Example 2 In the greenhouse the plants were barley (Hodeum vulgare), wheat (Triticum sativum), maize (Zea mays), small stinging nettle (Urtica urens), white goosefoot (Chenopodium album), chamomile (Matricaria chamomilla), chickweed (Stellaria media), annual bluegrass (Poa annua), black foxtail (Alopecurus myosuroides) at a height of 2.5 - 16 cm with 2-ethylamino-4-propoxyisopropylamino-6-chloro-s-triazine A, 2-isopropylamino-4-propoxyisopropylamino-6-chloro-s-triazine. B, 2-isopropylamino-4-propoxyisopropylamino-6-methoxy-s-triazine C, 2,4-bis (ethoxyisopropylamino) -6-methylmercaptos-triazine D and for comparison with 2-chloro-4,6-bis- <äthylamino) -striazine treated. The application rate was 1.5 kg of active ingredient per hectare, dispersed in 500 liters of water. After 3 weeks, the result shown in the table below became obtained: active ingredient A B C D barley 10 0-10 0-10 0-10 20-30 wheat 0-10 0-10 0-10 0-10 20-30 maize 10 0 10-20 10 0-10 kl. Brenneseel 90-100 90-100 90-100 90-100 90-100 w. goose foot 90-100 90-100 90-100 90-100 90-100 chamomile 90-100 90-100 90-100 90-100 80-90 chickweed 100 90-100 90-100 90-100 90 ann. Bluegrass 90-100 90-100 100 90-100 90 black foxtail 90-100 90-100 90-100 90-100 80 0 = no damage 100 = total damage

Claims (1)

Patentansprüche 1. Triazinderivate der allgemeinen Formel in der R1 ein Chlor- oder Bromatom oder eine Cyan-, Methoxy-oder Thiomethylgruppe, R2 einen Alkoxyalkylrest mit 5 bis 7 Kohlenstoffatomen, einem niederen Alkylthiosiopropylrest, einen thylthioäthylrest und R3 einen Alkoxyalkylrest mit 4 bis 7 Kohlenstoffatomen, einen niederen Alkylrest oder einen Alkylthioalkylrest mit 3 bis 5 Kohlenstoffatomen bedeuten, mit der Maßgabe, daß R2 zusätzlich einen Methylthioäthylrest bedeutet, wenn R3 einen Methylthioäthylrest.bedeutet 2. Herbizid, enthaltend ein Triazinderivat, wie im Anspruch 1 gekennzeichnet.Claims 1. Triazine derivatives of the general formula in which R1 is a chlorine or bromine atom or a cyano, methoxy or thiomethyl group, R2 is an alkoxyalkyl group with 5 to 7 carbon atoms, a lower alkylthiosropyl group, a thylthioethyl group and R3 is an alkoxyalkyl group with 4 to 7 carbon atoms, a lower alkyl group or an alkylthioalkyl group 3 to 5 carbon atoms, with the proviso that R2 also denotes a methylthioethyl radical when R3 denotes a methylthioethyl radical. 2. Herbicide containing a triazine derivative, as characterized in claim 1.
DE19691911527 1969-03-07 1969-03-07 Herbicidal triazine compounds Pending DE1911527A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19691911527 DE1911527A1 (en) 1969-03-07 1969-03-07 Herbicidal triazine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691911527 DE1911527A1 (en) 1969-03-07 1969-03-07 Herbicidal triazine compounds

Publications (1)

Publication Number Publication Date
DE1911527A1 true DE1911527A1 (en) 1970-11-26

Family

ID=5727364

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19691911527 Pending DE1911527A1 (en) 1969-03-07 1969-03-07 Herbicidal triazine compounds

Country Status (1)

Country Link
DE (1) DE1911527A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999029677A1 (en) * 1997-12-11 1999-06-17 Bayer Aktiengesellschaft Substituted 2,4-diamino-1,3,5-triazines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999029677A1 (en) * 1997-12-11 1999-06-17 Bayer Aktiengesellschaft Substituted 2,4-diamino-1,3,5-triazines

Similar Documents

Publication Publication Date Title
DE1915387A1 (en) herbicide
DE1770269A1 (en) New imidazole derivatives and herbicidal compositions containing them
DE1670315B1 (en) 1- (m-Trifluoromethylphenyl) -4-methoxy-5-halo-pyridazone- (6) derivatives
DE2005326A1 (en) Urea derivatives
DE2258243A1 (en) HETEROCYCLIC COMPOUNDS AND THEIR USES
DE1911527A1 (en) Herbicidal triazine compounds
DE2815689A1 (en) TRIAZINE COMPOUNDS, PROCESS FOR THE PRODUCTION OF THESE TRIAZINE COMPOUNDS, FURTHER HERBICIDAL AGENTS
DE2238042A1 (en) HETEROCYCLIC COMPOUNDS AND THEIR USES
DE1542813A1 (en) herbicide
DE1770343C3 (en) Compounds and their use as herbicidal active ingredients
DE1670289C3 (en) s-triazine derivatives
DE1542835A1 (en) Herbicides
DE1542687A1 (en) Herbicides
DE1542816A1 (en) Herbicides
DE1670100A1 (en) Herbicides
DE1670315C (en) 1 (m fluoromethylphenyl) 4 methoxy 5 halogen pyndazon (6) derivatives
DE1670289B2 (en) S-TRIAZINE DERIVATIVES
DE2115096A1 (en) Substituted chlorocarbonylureas
DE1913266A1 (en) herbicide
DE1913631A1 (en) Substituted hydantoins
DE1670291C3 (en) Substituted 2-amino-4-alkynylamino-triazines
DE1903466A1 (en) Substituted triazines
DE1920518A1 (en) herbicide
DE2126640C3 (en) Substituted diamino-s-triazines, processes for their preparation and their use for combating weeds
DE2141394A1 (en) Process for the preparation of new, herbicidally active (alkoxymethylamino) s-triazines