CH528211A - Selective herbicides - 1-aryl-3-methoxy-3-methyl-ureas - Google Patents
Selective herbicides - 1-aryl-3-methoxy-3-methyl-ureasInfo
- Publication number
- CH528211A CH528211A CH457369A CH457369A CH528211A CH 528211 A CH528211 A CH 528211A CH 457369 A CH457369 A CH 457369A CH 457369 A CH457369 A CH 457369A CH 528211 A CH528211 A CH 528211A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- formula
- ureas
- methyl
- weeds
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title description 3
- 241000196324 Embryophyta Species 0.000 claims abstract description 12
- 241000743985 Alopecurus Species 0.000 claims abstract description 6
- 235000013339 cereals Nutrition 0.000 claims abstract description 5
- 240000008042 Zea mays Species 0.000 claims abstract description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims abstract description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims abstract description 4
- 235000009973 maize Nutrition 0.000 claims abstract description 4
- 235000007320 Avena fatua Nutrition 0.000 claims abstract description 3
- 241000209764 Avena fatua Species 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 10
- 244000045561 useful plants Species 0.000 claims description 4
- 241000209140 Triticum Species 0.000 abstract description 5
- 235000021307 Triticum Nutrition 0.000 abstract description 5
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 abstract description 2
- 240000005979 Hordeum vulgare Species 0.000 abstract description 2
- 241000209056 Secale Species 0.000 abstract description 2
- 235000007238 Secale cereale Nutrition 0.000 abstract description 2
- 244000038559 crop plants Species 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- -1 carbamoyl halide Chemical class 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- 235000005781 Avena Nutrition 0.000 description 3
- 241000209761 Avena Species 0.000 description 3
- 241001101998 Galium Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- ZLCLNXPSGUUSBQ-UHFFFAOYSA-N 2-chloro-1-ethoxy-4-isocyanatobenzene Chemical compound CCOC1=CC=C(N=C=O)C=C1Cl ZLCLNXPSGUUSBQ-UHFFFAOYSA-N 0.000 description 1
- AJBZENLMTKDAEK-UHFFFAOYSA-N 3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-4,9-diol Chemical compound CC12CCC(O)C(C)(C)C1CCC(C1(C)CC3O)(C)C2CCC1C1C3(C)CCC1C(=C)C AJBZENLMTKDAEK-UHFFFAOYSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical class [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 1
- 235000003880 Calendula Nutrition 0.000 description 1
- 240000001432 Calendula officinalis Species 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 240000002635 Dendrocalamus asper Species 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- GCPXMJHSNVMWNM-UHFFFAOYSA-N arsenous acid Chemical class O[As](O)O GCPXMJHSNVMWNM-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Title ures of formula (I) (where R is ethoxy or ethylthio) are used for selectively combatting weeds in cultures of crop plants. (I) are particularly useful against Alopecurus and Avena fatua in cultures of cereals (wheat, barley, rye) and maize. High rates of application give a total herbicidal effect. Results of greenhouse trials demonstrating the pre- and post- emergence selective herbicidal action of (I) are given in the specification.
Description
Verwendung von Phenylharnstoffen zum selektiven Bekämpfen von Unkräutern in Kulturen von Nutzpflanzen
Die vorliegende Erfindung betrifft die Verwendung von Verbindungen der Formel
EMI1.1
worin R die C2H50- oder C2Hs-Gruppe bedeutet, zum selektiven Bekämpfen von Unkräutern in Kulturen von Nutzpflanzen, besonders in Kulturen von Getreide und Mais.
Die Herstellung der Verbindungen der Formel (I) kann nach an sich bekannten Methoden erfolgen, z. B. durch Reaktion von
EMI1.2
mit
EMI1.3
worin R die angegebene Bedeutung hat und A und B Reste bedeuten, die unter Anlagerung oder Kondensation Harnstoffe bilden. Dabei stellt eine der beiden Gruppen A und B ein Amin dar, während die andere ein Urethan, ein Carbamoylhalogenid, eine Harnstoffgruppe, oder insbesondere den Isocyanat- oder Isothiocyanatrest darstellt. Im letzteren Fall muss zum Austausch des S-Atoms gegen Sauerstoff eine Nachbehandlung mit einem Oxydationsmittel, z. B. HgO, Cl2/H20 oder COC12/H20, vorgenommen werden. R1 steht für eine Methylgruppe oder ein Wasserstoffatom. Im letzteren Fall, wenn also z. B. von Hydroxylamin ausgegangen wird, muss nach der Harnstoffbildung eine Nachmethylierung, z. B. mit Dimethylsulfat, folgen.
Die Verbindungen der Formel (I) weisen ausgesprochen selektivherbizide Eigenschaften im allgemeinen auf und erweisen sich als besonders vorteilhaft beim Bekämpfen von Unkräutern in Kulturen von Nutzpflanzen, insbesondere in Getreide- und Maiskulturen. Als Getreide werden hier Weizen, Gerste und Roggen, angesprochen. Besonders vorteilhaft ist die Wirkung gegen gradartige Unkräuter, wie insbesondere Alopecurus und Avena fatua. Dabei kommt der Verbindung der Formel
EMI1.4
besondere Bedeutung zu. Bei genügend grosser Aufwandmenge ist jedoch auch totalherbizide Wirkung vorhanden.
Die Anwendung der Wirkstoffe kann sowohl im Vorauflaufwie im Nachauflaufverfahren vorgenommen werden. Dabei können die Aufwandmengen in weiten Grenzen schwanken, z. B. zwischen 0,1 bis 10 kg Wirkstoff pro Hektare, vorzugsweise werden jedoch 0,5 bis 5 kg Wirkstoff pro Hektare eingesetzt.
Mittel, welche sich zur erfindungsgemässen Verwendung eignen, enthalten im allgemeinen ausser den Wirkstoffen der Formel (I) einen geeigneten Träger und/oder andere Zuschlagstoffe. Geeignete Träger und Zuschlagstoffe können fest oder flüssig sein und entsprechen den in der Formulierungstechnik üblichen Stoffen, wie z. B. natürlichen oder regenerierten mineralischen Stoffen, Lösungs-, Verdünnungs-, Dispergier-, Emulgier-, Netz-, Haft-, Verdickungs-, Bindeoder Düngmitteln. Ferner können noch weitere Herbizide zugesetzt werden. Solche Herbizide können z. B. der Klasse der Harnstoffe, gesättigten und ungesättigten Halogenfettsäuren, Halogenbenzonitrile, Halogenbenzoesäuren, Phenoxyalkylcarbonsäuren, Carbamate, Triazine, Nitroalkylphenole, quaternären Ammoniumsalze, Sulfaminsäure, Arsenate, Arsenite, Borate oder Chlorate angehören.
Zur Verwendung in Schädlingsbekämpfungsmitteln können die Verbindungen der Formel (I) als Stäubemittel, Emul sionskonzentrate, als Granulate, Dispersionen oder auch als Sprays, wie etwa bei der Gasphasenapplikation in Gewächshäusern, als Lösungen oder Aufschlämmungen in üblicher Formulierung, die zum Allgemeinwissen der Applikationstechnik gehört, verarbeitet werden. Man vergleiche entsprechende Angaben im Schweizer Patent Nr. 424 359.
Einige Beispiele werden weiter unten gegeben.
Beispiel 1
Man lässt unter leichter Kühlung und kräftigem Rühren zu einer Lösung von 68 g Methoxymethylamin in 120 ml Dioxan 199 g 3-Chlor-4-äthoxyphenylisocyanat zutropfen, rührt ohne Kühlung dann noch weitere 4 Stunden, verdünnt mit etwa 80 ml Wasser und saugt den auskristallisierten N-(3 -Chlor4-äthoxyph enyl)-N' -methyl-N' -methoxy-harnstoff ab.
Ausbeute: 95% Smp. 79-80 C [Verbindung (IV)]
Analog wird die Verbindung der Formel
EMI2.1
hergestellt.
Smp. 83-85 C
Formulierungs-Beispiele Stäubemittel
Gleiche Teile eines erfindungsgemässen Wirkstoffes und gefällte Kieselsäure werden fein vermahlen. Durch Vermischen mit Kaolin oder Talkum können daraus Stäubemittel mit bevorzugt 1-6 % Wirkstoffgehalt hergestellt werden.
Spritzpulver
Zur Herstellung eines Spritzpulvers werden beispielsweise die folgenden Komponenten gemischt und fein vermahlen: 50 Teile Wirkstoff 20 Teile Hisil (hoch adsorptive Kieselsäure) 25 Teile Bolus alba (Kaolin)
3,5 Teile Reaktionsprodukt aus p-tert. Octylphenol und Äthylenoxyd
1,5 Teile 1-benzyl-2-stearyl-benzimidazol-6 ,3' -disulfosaures
Natrium Emulsionskonzentrat
Durch Mischen von 20 Teilen Wirkstoff (IV)
12 Teilen einer Mischung einer nichtionogenen und einer anionaktiven oberflächenaktiven Verbindung
3 Teilen eines Kondensationsproduktes von 1 Mol Ricinusöl und 20-50 Mol Äthylenoxyd
5 Teilen Dimethylsulfoxyd 60 Teilen Isophoron erhält man ein 20%ges Emulsionskonzentrat, das sich mit Wasser auf eine beliebige Konzentration zu einer spritzfähigen Emulsion verdünnen lässt.
Beispiel 2
Im Gewächshaus wurden in Tontöpfen die in der unten folgenden Liste aufgeführten Pflanzen angesät. Die Prüfung erfolgte mit der Verbindung (IV) sowohl im Preemergent Verfahren einen Tag nach der Aussaat, als auch im Postemergent-Verfahren etwa 12 Tage nach der Aussaat. Die Auswertung erfolgte 21 bzw. 18 Tage nach der Applikation.
Als Vergleichssubstanz wurde der Wirkstoff der Formel
EMI2.2
EMI2.3
<tb> <SEP> re <SEP> -Pre- <SEP> <SEP> Post
<tb> <SEP> 1 <SEP> kg/ha <SEP> 2kg/ha <SEP> 1 <SEP> kg/ha <SEP> 2 <SEP> kg/ha
<tb> Pflanzen <SEP> IV <SEP> VI <SEP> IV <SEP> VI <SEP> IV <SEP> VI <SEP> IV <SEP> VI <SEP>
<tb> Hordeum <SEP> ,5 <SEP> 2,5 <SEP> 2, <SEP> 7 <SEP> 3 <SEP> 3 <SEP> 4,5 <SEP> 4
<tb> <SEP> Triticum <SEP> 1 <SEP> 1,5 <SEP> 1,5 <SEP> IV <SEP> 2 <SEP> 1 <SEP> 3 <SEP> 2,5 <SEP>
<tb> Avena <SEP> fat.
<SEP> 7,5 <SEP> 8,5 <SEP> 9 <SEP> 8,5 <SEP> 8 <SEP> 7 <SEP> 8,5 <SEP> 8
<tb> Alopecurus <SEP> 9 <SEP> 7 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 7,5 <SEP> 9 <SEP> 9
<tb> Poa <SEP> 9 <SEP> 5,5 <SEP> 9 <SEP> 9 <SEP> 7,5 <SEP> 8 <SEP> 9 <SEP> 9
<tb> Galium <SEP> 3 <SEP> 4,5 <SEP> 9 <SEP> 6 <SEP> 6,5 <SEP> 6,5 <SEP> 7,5 <SEP> 7
<tb> Stellaria <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9
<tb> Calendula <SEP> 9 <SEP> 8 <SEP> 9 <SEP> 9 <SEP> 8 <SEP> 7,5 <SEP> 9 <SEP> 9
<tb> Legende: 1 = keine Schäden
3 = gerade noch tolerierbare Schäden
9 = Totalschaden
Beispiel 3
Im Gewächshaus wurden in Tontöpfen die in der unten folgenden Tabelle aufgeführten Pflanzen angesät. Die Prüfung erfolgte mit der Verbindung IV sowohl im Preemergent Verfahren einen Tag nach der Aussaat als auch im Postemergent-Verfahren 12 Tage nach der Aussaat.
Die Auswertung erfolgte 21 bzw. 18 Tage nach der Applikation. Zur Applikation wurde ein 25 %iges Emulsionskonzentrat (A) (hergestellt analog Formulierungsbeispiel) und ein 50%iges Spritzpulver (B) verwendet.
EMI3.1
<tb>
<SEP> A <SEP> B <SEP>
<tb> <SEP> kg <SEP> Wirkstoff/ha <SEP> kg <SEP> Wirkstoff/ha
<tb> <SEP> Pflanzen <SEP> 3 <SEP> 2 <SEP> 1 <SEP> 0,5 <SEP> 3 <SEP> 2 <SEP> 1 <SEP> 0,5
<tb> <SEP> Triticum <SEP> 2 <SEP> 1 <SEP> 1 <SEP> 1 <SEP> 2 <SEP> 2 <SEP> 1 <SEP> 1
<tb> <SEP> Avena <SEP> fat. <SEP> 9 <SEP> 7 <SEP> 4 <SEP> 3 <SEP> 9 <SEP> 7 <SEP> 5 <SEP> 3
<tb> 1, <SEP>
<tb> m <SEP> Alopecurus <SEP> 9 <SEP> 9 <SEP> : <SEP> 8 <SEP> 5 <SEP> 9 <SEP> 9 <SEP> 7 <SEP> 5
<tb> <SEP> Galium <SEP> 7 <SEP> 6 <SEP> 4 <SEP> 3 <SEP> 7 <SEP> 7 <SEP> 3 <SEP> 3
<tb> <SEP> Triticum <SEP> 3 <SEP> 3 <SEP> 1 <SEP> 1 <SEP> 2 <SEP> 1 <SEP> 1 <SEP> 1
<tb> Avena <SEP> fat.
<SEP> 9 <SEP> 8 <SEP> 7 <SEP> 5 <SEP> 8 <SEP> 7 <SEP> 7 <SEP> 5 <SEP>
<tb> Alopecurus <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 7 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 7
<tb> <SEP> Galium <SEP> 8 <SEP> 8 <SEP> 8 <SEP> 6 <SEP> 7 <SEP> 7 <SEP> 7 <SEP> 6
<tb> Legende: 1 = keine Schäden
3 = gerade noch tolerierbare Schäden
9 = Totalschaden
Use of phenylureas for the selective control of weeds in crops of useful plants
The present invention relates to the use of compounds of the formula
EMI1.1
wherein R is the C2H50 or C2Hs group, for the selective control of weeds in crops of useful plants, especially in crops of cereals and maize.
The compounds of formula (I) can be prepared by methods known per se, e.g. B. by reaction of
EMI1.2
With
EMI1.3
wherein R has the meaning given and A and B are radicals which form ureas with addition or condensation. One of the two groups A and B represents an amine, while the other represents a urethane, a carbamoyl halide, a urea group, or in particular the isocyanate or isothiocyanate radical. In the latter case, an aftertreatment with an oxidizing agent, e.g. B. HgO, Cl2 / H20 or COC12 / H20 can be made. R1 stands for a methyl group or a hydrogen atom. In the latter case, so if z. B. is assumed from hydroxylamine, must after the urea formation, a Nachmethylierung, z. B. with dimethyl sulfate, follow.
The compounds of the formula (I) generally have markedly selective herbicidal properties and prove to be particularly advantageous in controlling weeds in crops of useful plants, in particular in cereal and maize crops. Wheat, barley and rye are referred to as grain here. The action against straight weeds, such as in particular Alopecurus and Avena fatua, is particularly advantageous. Here comes the compound of the formula
EMI1.4
particular importance to. With a sufficiently large application rate, however, there is also a total herbicidal effect.
The active ingredients can be used both pre-emergence and post-emergence. The application rates can vary within wide limits, e.g. B. between 0.1 to 10 kg of active ingredient per hectare, but preferably 0.5 to 5 kg of active ingredient per hectare are used.
Agents which are suitable for use according to the invention generally contain, in addition to the active ingredients of the formula (I), a suitable carrier and / or other additives. Suitable carriers and additives can be solid or liquid and correspond to the substances customary in formulation technology, such as. B. natural or regenerated mineral substances, solvents, thinners, dispersants, emulsifiers, wetting agents, adhesives, thickeners, binders or fertilizers. Further herbicides can also be added. Such herbicides can e.g. B. belong to the class of ureas, saturated and unsaturated halogenated fatty acids, halogenobenzonitriles, halogenobenzoic acids, phenoxyalkylcarboxylic acids, carbamates, triazines, nitroalkylphenols, quaternary ammonium salts, sulfamic acid, arsenates, arsenites, borates or chlorates.
For use in pesticides, the compounds of the formula (I) can be used as dusts, emulsion concentrates, as granules, dispersions or also as sprays, for example in the case of gas phase application in greenhouses, as solutions or slurries in the usual formulation, which is part of general knowledge of application technology, are processed. Compare the corresponding information in Swiss Patent No. 424 359.
Some examples are given below.
example 1
With slight cooling and vigorous stirring, 199 g of 3-chloro-4-ethoxyphenyl isocyanate are added dropwise to a solution of 68 g of methoxymethylamine in 120 ml of dioxane - (3 -Chlor4-ethoxyphenyl) -N '-methyl-N' -methoxy-urea.
Yield: 95% mp 79-80 C [compound (IV)]
The compound of the formula is analogous
EMI2.1
manufactured.
M.p. 83-85 C
Formulation examples dust
Equal parts of an active ingredient according to the invention and precipitated silica are finely ground. By mixing it with kaolin or talc, it can be used to produce dusts with preferably 1-6% active ingredient content.
Wettable powder
To produce a wettable powder, for example, the following components are mixed and finely ground: 50 parts of active ingredient 20 parts of Hisil (highly adsorptive silica) 25 parts of Bolus alba (kaolin)
3.5 parts of reaction product from p-tert. Octylphenol and ethylene oxide
1.5 parts of 1-benzyl-2-stearyl-benzimidazole-6, 3'-disulfonic acid
Sodium emulsion concentrate
By mixing 20 parts of active ingredient (IV)
12 parts of a mixture of a nonionic and an anionic surface-active compound
3 parts of a condensation product of 1 mol of castor oil and 20-50 mol of ethylene oxide
5 parts of dimethyl sulfoxide and 60 parts of isophorone give a 20% total emulsion concentrate which can be diluted with water to any concentration to form a sprayable emulsion.
Example 2
The plants listed below were sown in clay pots in the greenhouse. The test was carried out with the compound (IV) both in the pre-emergent method one day after sowing and in the post-emergent method about 12 days after sowing. The evaluation took place 21 and 18 days after the application.
The active ingredient of the formula was used as the comparison substance
EMI2.2
EMI2.3
<tb> <SEP> re <SEP> -Pre- <SEP> <SEP> Post
<tb> <SEP> 1 <SEP> kg / ha <SEP> 2kg / ha <SEP> 1 <SEP> kg / ha <SEP> 2 <SEP> kg / ha
<tb> Plants <SEP> IV <SEP> VI <SEP> IV <SEP> VI <SEP> IV <SEP> VI <SEP> IV <SEP> VI <SEP>
<tb> Hordeum <SEP>, 5 <SEP> 2,5 <SEP> 2, <SEP> 7 <SEP> 3 <SEP> 3 <SEP> 4,5 <SEP> 4
<tb> <SEP> Triticum <SEP> 1 <SEP> 1.5 <SEP> 1.5 <SEP> IV <SEP> 2 <SEP> 1 <SEP> 3 <SEP> 2.5 <SEP>
<tb> Avena <SEP> fat.
<SEP> 7.5 <SEP> 8.5 <SEP> 9 <SEP> 8.5 <SEP> 8 <SEP> 7 <SEP> 8.5 <SEP> 8
<tb> Alopecurus <SEP> 9 <SEP> 7 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 7,5 <SEP> 9 <SEP> 9
<tb> Poa <SEP> 9 <SEP> 5.5 <SEP> 9 <SEP> 9 <SEP> 7.5 <SEP> 8 <SEP> 9 <SEP> 9
<tb> Galium <SEP> 3 <SEP> 4.5 <SEP> 9 <SEP> 6 <SEP> 6.5 <SEP> 6.5 <SEP> 7.5 <SEP> 7
<tb> Stellaria <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 9
<tb> Calendula <SEP> 9 <SEP> 8 <SEP> 9 <SEP> 9 <SEP> 8 <SEP> 7,5 <SEP> 9 <SEP> 9
<tb> Legend: 1 = no damage
3 = damage that is barely tolerable
9 = total loss
Example 3
The plants listed in the table below were sown in clay pots in the greenhouse. The test was carried out with compound IV both in the pre-emergent method one day after sowing and in the post-emergent method 12 days after sowing.
The evaluation took place 21 and 18 days after the application. A 25% emulsion concentrate (A) (prepared analogously to the formulation example) and a 50% wettable powder (B) were used for application.
EMI3.1
<tb>
<SEP> A <SEP> B <SEP>
<tb> <SEP> kg <SEP> active ingredient / ha <SEP> kg <SEP> active ingredient / ha
<tb> <SEP> Plants <SEP> 3 <SEP> 2 <SEP> 1 <SEP> 0.5 <SEP> 3 <SEP> 2 <SEP> 1 <SEP> 0.5
<tb> <SEP> Triticum <SEP> 2 <SEP> 1 <SEP> 1 <SEP> 1 <SEP> 2 <SEP> 2 <SEP> 1 <SEP> 1
<tb> <SEP> Avena <SEP> fat. <SEP> 9 <SEP> 7 <SEP> 4 <SEP> 3 <SEP> 9 <SEP> 7 <SEP> 5 <SEP> 3
<tb> 1, <SEP>
<tb> m <SEP> Alopecurus <SEP> 9 <SEP> 9 <SEP>: <SEP> 8 <SEP> 5 <SEP> 9 <SEP> 9 <SEP> 7 <SEP> 5
<tb> <SEP> Galium <SEP> 7 <SEP> 6 <SEP> 4 <SEP> 3 <SEP> 7 <SEP> 7 <SEP> 3 <SEP> 3
<tb> <SEP> Triticum <SEP> 3 <SEP> 3 <SEP> 1 <SEP> 1 <SEP> 2 <SEP> 1 <SEP> 1 <SEP> 1
<tb> Avena <SEP> fat.
<SEP> 9 <SEP> 8 <SEP> 7 <SEP> 5 <SEP> 8 <SEP> 7 <SEP> 7 <SEP> 5 <SEP>
<tb> Alopecurus <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 7 <SEP> 9 <SEP> 9 <SEP> 9 <SEP> 7
<tb> <SEP> Galium <SEP> 8 <SEP> 8 <SEP> 8 <SEP> 6 <SEP> 7 <SEP> 7 <SEP> 7 <SEP> 6
<tb> Legend: 1 = no damage
3 = damage that is barely tolerable
9 = total loss
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH457369A CH528211A (en) | 1969-03-26 | 1969-03-26 | Selective herbicides - 1-aryl-3-methoxy-3-methyl-ureas |
| ES366189A ES366189A1 (en) | 1968-04-19 | 1969-04-18 | Procedure for the preparation of phenilureas. (Machine-translation by Google Translate, not legally binding) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH457369A CH528211A (en) | 1969-03-26 | 1969-03-26 | Selective herbicides - 1-aryl-3-methoxy-3-methyl-ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH528211A true CH528211A (en) | 1972-09-30 |
Family
ID=4278602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH457369A CH528211A (en) | 1968-04-19 | 1969-03-26 | Selective herbicides - 1-aryl-3-methoxy-3-methyl-ureas |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH528211A (en) |
-
1969
- 1969-03-26 CH CH457369A patent/CH528211A/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |