DE2022228A1 - New phosphonic acid esters - Google Patents
New phosphonic acid estersInfo
- Publication number
- DE2022228A1 DE2022228A1 DE19702022228 DE2022228A DE2022228A1 DE 2022228 A1 DE2022228 A1 DE 2022228A1 DE 19702022228 DE19702022228 DE 19702022228 DE 2022228 A DE2022228 A DE 2022228A DE 2022228 A1 DE2022228 A1 DE 2022228A1
- Authority
- DE
- Germany
- Prior art keywords
- amine
- cyclohexyl
- phosphonyl
- cyolohexyl
- oyclohexyl
- 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.)
- Granted
Links
- 150000003008 phosphonic acid esters Chemical class 0.000 title claims description 7
- 241000196324 Embryophyta Species 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 240000006694 Stellaria media Species 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000003337 fertilizer Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 12
- 125000005499 phosphonyl group Chemical group 0.000 claims 7
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 241000828585 Gari Species 0.000 claims 2
- 241001310793 Podium Species 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 claims 2
- 230000008635 plant growth Effects 0.000 claims 2
- 240000006122 Chenopodium album Species 0.000 claims 1
- 235000009344 Chenopodium album Nutrition 0.000 claims 1
- 240000003705 Senecio vulgaris Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003905 agrochemical Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 1
- 230000005158 plant movement Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000780602 Senecio Species 0.000 description 2
- 241000404539 Tripleurospermum Species 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229920000847 nonoxynol Polymers 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BMZZGIWIRFMFOU-UHFFFAOYSA-N 4-cyclohexylidenebutan-1-amine Chemical compound NCCCC=C1CCCCC1 BMZZGIWIRFMFOU-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000214240 Galinsoga parviflora Species 0.000 description 1
- 235000018914 Galinsoga parviflora Nutrition 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000209048 Poa Species 0.000 description 1
- 244000292693 Poa annua Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 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 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- RPFGCUFAJAQNLJ-UHFFFAOYSA-N n-phenylcyclohexanimine Chemical compound C1CCCCC1=NC1=CC=CC=C1 RPFGCUFAJAQNLJ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- PRAHMDIEZMWIRW-UHFFFAOYSA-N propyl dihydrogen phosphite Chemical compound CCCOP(O)O PRAHMDIEZMWIRW-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000010454 slate 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
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008096 xylene 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fertilizers (AREA)
- Cultivation Of Plants (AREA)
Description
VEB CHEMIEKOMBIWAiP BITTEEFELD Bitterfeld, 22.JuIi 1969VEB CHEMIEKOMBIWAiP BITTEEFELD Bitterfeld, June 22, 1969
4.04.20/11034.04.20 / 1103
Erfinder: Dr. Eberhard Günther, 'Leipzig Dr. Wilhelm Lb'ttge, WolfenInventor: Dr. Eberhard Günther, 'Leipzig Dr. Wilhelm Lb'ttge, Wolfen
Die Erfindung betrifft neue Phosphonsäureester der allgemeinen FormelThe invention relates to new phosphonic acid esters in general formula
NH -NH -
H
0H
0
in der R1, R2 und'B3... Alkyl, Aryl und/oder Cyoloalkyl, die auoh substituiert sein können, und X Wasserstaff, Halogen* Nitro-j Cyano-, Alkyl-, Alkoxy- oder Alkylmsrcaptogruppen darstellen.in which R 1 , R 2 and B 3 ... alkyl, aryl and / or cyoloalkyl, which may also be substituted, and X represent hydrogen, halogen * nitro-j cyano, alkyl, alkoxy or alkylmacapto groups.
Die Erfindung umfaßt, weiterhin Mittel zur Beeinflussung, insbesondere Hemmung bzw. Verhinderung unerwUnsohten Pflanzenwaohsturns sowie eur. selektiven UnkrautbekämpfungThe invention further comprises means for influencing in particular, inhibition or prevention of unexpected unexpected events Plant Waohsturns as well as eur. selective weed control
109808/2223109808/2223
- 2 - 4.04- 2 - 4.04
.»28 . " 28
in Kulturpflanzen, welche die obengenannten neuen Phosphorsäureester als Wirkstoff enthalten, sowie ein Verfahren zur Herstellung dieser neuen Phosphonsäureester.in crops which contain the above-mentioned new phosphoric acid esters as an active ingredient, as well as a process for the production of these new phosphonic acid esters.
Die neuen Verbindungen werden in hohen Ausbeuten erhalten, indem man Phosphorigsäureester der allgemeinen Formel The new compounds are obtained in high yields by adding phosphorous acid esters of the general formula
R1O 0R 1 O 0
mit N-Cyclohexyiidenaminen der allgemeinen Pormelwith N-Cyclohexyiidenaminen of the general formula
umsetzt. In den Formeln steht X für H, Alkyl, Halogen, Nitro, Cyano, Alkoxy, Alkylmercapto und S^, R2 und R^ für Alkyl—, Aryl- und/oder Cycloalkylrestej die auch substituiert sein können.implements. In the formulas, X stands for H, alkyl, halogen, nitro, cyano, alkoxy, alkylmercapto and S ^, R 2 and R ^ for alkyl, aryl and / or cycloalkyl radicals, which can also be substituted.
Sie erfindungsgemäßen Phosphonsäureester stellen Festprodukte oder Öle dar, die sich in bekannten organischen Lösungsmitteln wie z. B. Alkohol, Aceton oder Benzol leicht lösen. Die Additionsreaktion kann mit den reinenYou phosphonic acid esters according to the invention are solid products or oils, which are in known organic solvents such as. B. alcohol, acetone or benzene solve easily. The addition reaction can with the pure
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AuQgangskomponenten oder in Lösungsmitteln «ie z. B. Benzol, Chloroform oder Tetrachlorkohlenstoff, gegebenenfalls unter Zugabe eines basischen Katalysators, «ie ζ« Β« Triäthylamin oder Natriumalkoholat vorgenommen werden.Output components or in solvents «ie z. B. benzene, Chloroform or carbon tetrachloride, optionally with the addition of a basic catalyst, "ie ζ" Β "triethylamine or sodium alcoholate can be made.
Eb wurde weiterhin gefunden, daß die vorstehend angeführte Gruppe von Phosphorsäureestern herbizide Büttel darstellen, die sowohl im Vorauflauf als auch im Naehauflauf als Unkrautbekämpfungsmittel zur Anwendung gebraoht werden können·Eb was further found to be the above Group of phosphoric acid esters represent herbicidal Büttel, both in the pre-emergence and in the near-emergence be brewed as herbicides for use can·
Sie erfindungsgemäßen Mittel können in bekannter Weise, d. h. in Lösung oder auf Trägern in Form eines benetzbaren Pulvers, einer staubförmigen oder granulierten Substanz oder einer Emulsion verwendet werden«You can agents according to the invention in a known manner, d. H. in solution or on carriers in the form of a wettable powder, a dusty or granulated substance or an emulsion «
Die Darstellung benetzbarer Pulver und Emulsionskonzentrate ist an sich bekannt und erfordert außer den Träger™ stoffen oberflächenaktive Substanzen, wie z. B. äthoxyliertes Nony!phenol oder Alkylsulfonate· Als feste Trägerstoffe eignen sich beispielsweise Tone, Harze, Polymere, Schiefermehl und Kreide, und als flüssige Trägerstoffe sind Wasser, Alkohole, aromatische Kohlenwasserstoffe, Erdölfraktionen und chlorierte Kohlenwasserstoffe geeignet.The preparation of wettable powders and emulsion concentrates is known per se and also requires the carrier ™ substances surface-active substances, such as. B. ethoxylated Nony! Phenol or alkyl sulfonates · As solid carriers Clays, resins, polymers, slate powder and chalk are suitable, for example, and are suitable as liquid carriers Water, alcohols, aromatic hydrocarbons, petroleum fractions and chlorinated hydrocarbons are suitable.
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Die erfindungsgemäßen Verbindungen können auch mit Düngemitteln oder anderen Pestiziden und Herbiziden gemischt und gemeinsam ausgebracht werden.The compounds of the invention can also be mixed with fertilizers or other pesticides and herbicides and spread together.
1 Mol N-Cyclohexyliden-anilin wird in einer Rührapparatur unverdünnt vorgelegt. Anschließend tropft man 1 Mol Diäthylphosphit bis zum Anstieg der Eeaktionstemperatur auf 50 0C zu« Nachdem die Eeaktionsmischung über Nacht stand, kann die kristalline Verbindung verwendet werden.1 mol of N-cyclohexylidene-aniline is placed undiluted in a stirring apparatus. Subsequently added dropwise 1 mol of diethyl phosphite to the increase in Eeaktionstemperatur at 50 0 C on «After the Eeaktionsmischung stand overnight, the crystalline compound can be used.
1 Mol N-Cyclohexyliden-butylamin und 250 ml Benzol werden in einer Rührapparatur vorgelegt und 1 Mol Diis<spropylphosphit unter Rühren zugetropft. Dabei darf die Reaktionstemperatur bis 50 0C ansteigen. Die Mischung wird nun 1 bis 2 Stunden bei 50 bis 60 0C gehalten. Anschließend werden Benzol und Reste des Phosphites im Vakuum abdestilliert. Der Phosphonsäureester verbleibt als öliger Rückstand. 1 mol of N-cyclohexylidene-butylamine and 250 ml of benzene are placed in a stirring apparatus and 1 mol of diis propyl phosphite is added dropwise with stirring. The reaction temperature is allowed to rise to 50 0 C. The mixture is now held at 50 to 60 ° C. for 1 to 2 hours. Then benzene and residues of the phosphite are distilled off in vacuo. The phosphonic acid ester remains as an oily residue.
In der Tabelle I sind Beispiele der erfindungsgemäßen Verbindungen enthalten.In Table I are examples of the compounds according to the invention contain.
50 Teile N-m-Methylphenyl-N-Ci-COyO-dimethylphosphonyl-»50 parts of N-m-methylphenyl-N-Ci-COyO-dimethylphosphonyl- »
cyclohexyl)-amin werden mit 40 Teilen Kaolin, 6 Teilen ZeIl-cyclohexyl) amine with 40 parts of kaolin, 6 parts of ZeIl-
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pech und 4 Teilen äthoxyliertem Nonylphenol innig vermischt und -in einer geeigneten Mühle vermählen. Das entstandene Spritzpulver gibt mit Wasser benetzbare, herbizid wirkende Suspensionen.pitch and 4 parts of ethoxylated nonylphenol intimately mixed and-ground in a suitable mill. The resulting Wettable powder gives water-wettable, herbicidal suspensions.
20 Teile. N-OyClOhSXyI-N-(I-(O,O-diisopropylphosphonyl)-cyclohexyl)-amin werden in einem Gemisch, bestehend aus 40 Teilen Xylol und 30 Teilen Methylcyclohexanon gelöst und mit 7 Teilen äthoxyliertem Nonylphenol und 3 Teilen Calciumdodecylbenzolsulfonat vermischt. Das entstandene homogene Emulsionskonzentrat kann mit Wasser zu stabilen, herbizid wirkenden Spritzbrühen verdünnt werden.20 parts. N-OyClOhSXyI-N- (I- (O, O-diisopropylphosphonyl) -cyclohexyl) -amine are dissolved in a mixture consisting of 40 parts of xylene and 30 parts of methylcyclohexanone and mixed with 7 parts of ethoxylated nonylphenol and 3 parts of calcium dodecylbenzenesulfonate. The resulting homogeneous emulsion concentrate can be diluted with water to form stable, herbicidal spray mixtures.
Die Aktivität, der erfindungsgemäßen Verbindungen als vor dem Auflaufen .verabreichte Herbizide wurde dadurch ermittelt, daß Unkrautsamen in Böden ausgesät und deren Aussaaten kurz danach oberflächig mit den erfindungsgemäßen Verbindungen behandelt wurden. Angewendet wurden !0 kg AS/ha als 50 #iges Spritzpulver in 600 1 Wasser/ha oder als acetonische Lösung. Als Testpflanzen dienten Stellaria media, Senecio. vulgaris, Tripleurospermum inodora, Ohenopodlum album, Galinsoga parviflora und Poa annua. Die Bndauswertung erfolgte am 28. Tage nach der Sprltzung. DieThe activity of the compounds according to the invention than before Herbicides administered after emergence were determined by that weed seeds sown in soils and their sowing shortly thereafter superficially with the inventive Connections were dealt with. We used! 0 kg AS / ha as a 50 # wettable powder in 600 1 water / ha or as an acetone solution. Stellaria served as test plants media, Senecio. vulgaris, Tripleurospermum inodora, Ohenopodlum album, Galinsoga parviflora and Poa annua. The band evaluation was carried out on the 28th day after the spraying. the
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Resultate wurden nach einer bestimmten Skala mit den Noten I bis 9 bewertet. Dabei bedeutet der Wert 1, daß 95 % und mehr des Unkrautbestandes vernichtet sind. Der Wert 9 bedeutet keine Wirksamkeit. Die mit einigen der erfindungsgemäßen Verbindungen gewonnenen Ergebnisse gehen aus der Tabelle II hervor. Die Nummern der Verbindungen beziehen sich auf die Nummern in Tabelle I.Results were rated from I to 9 on a specific scale. The value 1 means that 95 % or more of the weed population has been destroyed. The value 9 means no effectiveness. The results obtained with some of the compounds of the invention are shown in Table II. The compound numbers refer to the numbers in Table I.
Die Aktivität der erflndungegemäßen Verbindungen als naoh dem Auflaufen verabreichte Herbizide wurde dadurch ermittelt} daß wäßrige Suspensionen oder acetonlsche Lösungen auf Pflanzen, die sich im Keimblatt- bis Zweilaubblattstadluiu befanden, gespritzt wurden. Angewendet wurden 4 und 10 kg ÄS/ha als 50 j&ige Spritzpulver oder acetonische Lösungen. Als Testpflanzen dienten Sinapis arvensis, Stellaria media, Senecio vulgarls, Tripleurospermum inodora, Chenopodlum album, Oiaiinsoga parvlflora, Avena sativa und Poa anniia. Die findausWertung erfolgte am 14. Tage naoh der Spritzimg. Die Ergebnisse wurden nach einer bestimmten Skala mit den Noten I bis 9 bewertet. Dabei bedeutet 1, daß 95 % und mehr des Unkrautbestandes vernichtet sind. Der · Wert 9 bedeutet keine Wirksamkeit. Die mit einigen der flndungegemäßen Verbindungen gewonnenen Ergebnisse gehen aus der Tabelle III hervor. Die Nummern der "lbindungen beziehen sioh auf die Nummern in Tabelle I.The activity of the compounds according to the invention as herbicides administered after emergence was determined by spraying aqueous suspensions or acetone solutions onto plants which were in the cotyledon to two-leaf state. 4 and 10 kg of AS / ha were used as 50% spray powder or acetone solutions. Sinapis arvensis, Stellaria media, Senecio vulgarls, Tripleurospermum inodora, Chenopodlum album, Oiaiinsoga parvlflora, Avena sativa and Poa anniia were used as test plants. The evaluation took place on the 14th day after the injection. The results were rated from I to 9 on a specific scale. 1 means that 95 % or more of the weed population has been destroyed. The value 9 means no effectiveness. The results obtained with some of the inappropriate compounds are shown in Table III. The numbers of the "bonds" refer to the numbers in Table I.
109808/2223109808/2223
-7- 4.04.20/1103-7- 4.04.20 / 1103
Wie aus der Tabelle IIIersichtlich ist, sseigen die Verbindungen gegenüber einseinen Fflanseoarten ein selektive B Verhalten (z.B.Huasmer 21 und 22), das besonders bei geringen Dosierungen in Erscheinung tritt« Zur Ermittlung der nutzbaren selektiven Wirksamkeit wurden Kulturpflanzen, zum Beispiel Zuckerrüben vor beziehungsweise nach dem Auflaufen mit den erfindungsgemäßen Verbindungen mit 4 bis 10 kg AS/ha behandelt. Die Spritaung erfolgte entweder kurz nach der Aussaat oder im Zwei- ti« Tierblattstadium der Pflanzen. Di® Endauswertung wurde bei den Vorauf lauf---anwendungen as 28» Tage und bei den la©häuflaufanwendungen am 14. Sage nach der Spritzung vorgenommen. Die Ergebnisse wurden nach einer bestimmten Skala mit den Koten 1 bis 9 bewertet. Dabei bedeutet der Wert i, daß sämtliche Kulturpflanzen vernichtet wurden. Beim Wert 9 wurden keine Sohäden an Kulturpflanzen registriert. Die zum Beispiel mit der erfindungsgemäßen Verbindung Nummer 21 in der Haohäuf laufanwendung gewonnenen Ergebnisse gehen aus der Tabelle IV hervor.As can be seen from Table III, the compounds are seperate a selective one compared to one of its fflanseo species B behavior (e.g. Huasmer 21 and 22), which is particularly important for low doses appears «To determine the usable selective effectiveness were cultivated plants, for example sugar beet before or after Emergence with the compounds according to the invention with 4 to 10 kg AS / ha treated. The injection took place either shortly after sowing or in the animal leaf stage of the plants. The final evaluation was made for the pre-emergence applications as 28 »days and with la © frequent applications made on the 14th day after the spraying. The results were graded from 1 to on a specific scale 9 rated. The value i means that all the crop plants have been destroyed. If the value was 9, there were none Registered soils on cultivated plants. For example with the inventive compound number 21 in the Results obtained from the most frequent application are derived from the Table IV.
10 98 08/22 2310 98 08/22 23
Claims (1)
I1
I.
phosphonyl)-cyolohexyl)-a_inHpC chlorophenyl-N- (1 - (Q, O-disse thyl-
phosphonyl) -cyolohexyl) -a_in
phosphonyl)-oyoIohexy1)-aminNo-MethylOhenyl-N-C1- (0, O-dimethyl-
phosphonyl) -oyoIohexy1) -amine
nyij-cycIohexyl)-a_inK-Pheayl-N- (1- (0,0-dimethylphospho-
nyij-cyclohexyl) -a_in
106 0C N>
K) Ö
106 0 C N>
K)
phosphonyl)-oyelohexyl)-aminN-Cyclo.'he3cyl-N- (1 - (Op-dime thy 1-
phosphonyl) -oyelohexyl) -amine
ro
ro
fSJO
ro
ro
fSJ
phonyi;-cyclohexyl)~aminN-Benzyl-N- (1- (O, 0-dimethylphos-
phonyi; -cyclohexyl) ~ amine
raethylphosphonyl)-cyclohexyl)~aminNp-methoxyphenyl-N- (1- (0,0-di-
methylphosphonyl) cyclohexyl) amine
methylphosphonyl)-oyclohexyl)-aminN-2,4-dichlorophenyl-N- (1- (0,0-di-
methylphosphonyl) -oyclohexyl) -amine
thylphosphonyl)-cyclohexyl)-aminNo-methoxyphenyl-N- (i- (0,0-dime ~
thylphosphonyl) cyclohexyl) amine
phosphonyl)-cyclohexyl)-arainN-4-piperidyl-N- (i ~ (0,0-dimethyi-
phosphonyl) cyclohexyl) arain
phosphonyl)-cyclohexyl)-aminN-phenyl-N- (1- (O, 0-diethyl-
phosphonyl) cyclohexyl amine
äthyIpho sphonyl)-cycIo hexyl)-aminNo-Methylpheny1-N- (I- (O, O-di-
Ethylpho-sphonyl) -cycIo hexyl) -amine
Ο'Ο '
phosphonyl)-cyolohe3cyl3-aminNm-methylphenyl-N- (1- (0,0-diethyl-
phosphonyl) -cyolohe3cyl3-amine
äthylphosphonyl)-cyclohexyl)-aminNp-methylphenyl-N- (1- (0,0-di-
ethylphosphonyl) cyclohexyl amine
ι92 0 C 1
ι
äthylphosphonyl)-cyclohexyl)-aminNo-chlorophenyl-N- (1- (0,0-di-
ethylphosphonyl) cyclohexyl amine
äthylphosphonyl)-oyclohexyl)-aminNpc chlorophenyl-rN. * (1 - (0,0-di-
ethylphosphonyl) -oyclohexyl) -amine
O122 0 C
O
äthylphosphonyl/-oyclohexyl)-aminNp-Metlioxyphenvl-li- (1 - (0, O-di chloro-
ethylphosphonyl / -oyclohexyl) amine
Br-Cyclohexyl-N-Ci-CO,0-dichlor-
äth.ylphosphonyl3-cyolohexyl)-amin ■ '' ■ ■ ■ ■ '■' ■ ■ ■.
Br-Cyclohexyl-N-Ci-CO, 0-dichloro
Ethylphosphonyl3-cyolohexyl) amine
.ολfr.
.ολ
propylphosphonyl)"-cyolohexyl)-aminN-cycloliexyl-ir-C 1 - (0,0-diiso-
propylphosphonyl) "cyolohexyl) amine
nyl)-cyelohexyl)-amin yCC ^
nyl) -cyelohexyl) -amine
propylphosphonyl)-cyclohexyl)-amlnN-methoxyethyl-N- (1- (0,0-diiso-
propylphosphonyl) -cyclohexyl) -amln
α Ni
α
propylphosphonyl)-cyclohexyl)-aminN-methoxypropyl-N- (i- (0,0-diiso-
propylphosphonyl) cyclohexyl amine
butylphosphonyl)-cyclohexyl)-aminN-methoxypropyl-N- (1- (0,0-diiso-
butylphosphonyl) cyclohexyl amine
butyip ho sp honyl)-c ycIo hexyl)-aminN-methoxyethy1-N- (I- (O, 0-diiso-
butyip ho sp honyl) -c ycIo hexyl) -amine
phosphonyl)-cyclohexyl)-aminN-methoxyethy1-N- (I- (O.0-diarayl-
phosphonyl) cyclohexyl amine
t1.4625 ^
t
phosphonyl;-2-methyl-cycIohexyl)-aminN-cyclohexyl- (i- (0,0-diisopropyl-
phosphonyl; -2-methyl-cyclohexyl) amine
phonyl)-2-methyl-cyclohexyl)-aminN-butyl-N- (i-CO, 0-diisobutyl-phos-
phonyl) -2-methyl-cyclohexyl) amine
Verbindung
It.Tabelle INo. of
link
It.Table I
kg AS/haApplication rate
kg AS / ha
ria mediaStella
ria media
vulgarisSenecio
vulgaris
spermum
inodoraTriple-euro
sperm
inodora
albumChenopodium
album
ga par-
vifloraGalinso-
ga par-
viflora
annuaPora
annua
NiVJ
Ni
CO CD
CO
Ni
QONi
Ni
QO
CD co
CD
4342
43
1010
10
12
1
31
3
31
3
11
1
11
1
11
1
K>CO
K>
roro
: ■■■■'■■ ν ■ ; ■ : ■■■■ '■■ ν ■ ; ■
■-■■^■.-■■c^'■' ■■ -. K ^
■ - ■■ ^ ■ .- ■■ c ^
NJNJ
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD14156069 | 1969-08-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2022228A1 true DE2022228A1 (en) | 1971-02-18 |
| DE2022228C2 DE2022228C2 (en) | 1982-11-04 |
Family
ID=5481515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702022228 Expired DE2022228C2 (en) | 1969-08-04 | 1970-05-06 | New phosphonic acid esters |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT300454B (en) |
| CH (1) | CH541278A (en) |
| DE (1) | DE2022228C2 (en) |
| FR (1) | FR2056340A5 (en) |
| HU (1) | HU162750B (en) |
| NL (1) | NL164863C (en) |
| RO (1) | RO62001A (en) |
| SU (2) | SU504781A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855363A (en) * | 1973-08-08 | 1974-12-17 | Upjohn Co | Cycloalkane, cycloalkene, and cycloalkanone phosphonates |
| US4061697A (en) * | 1974-12-17 | 1977-12-06 | Bayer Aktiengesellschaft | Phosphorus containing flame retarding agents which are reactive with isocyanates |
-
1970
- 1970-04-07 NL NL7004960A patent/NL164863C/en not_active IP Right Cessation
- 1970-05-06 DE DE19702022228 patent/DE2022228C2/en not_active Expired
- 1970-05-11 CH CH694670A patent/CH541278A/en not_active IP Right Cessation
- 1970-05-12 AT AT04268/70A patent/AT300454B/en not_active IP Right Cessation
- 1970-06-11 RO RO6360670A patent/RO62001A/en unknown
- 1970-06-23 SU SU1446651A patent/SU504781A1/en active
- 1970-06-24 FR FR7023412A patent/FR2056340A5/en not_active Expired
- 1970-08-04 HU HUCE000774 patent/HU162750B/hu unknown
-
1972
- 1972-06-26 SU SU721446651D patent/SU574195A1/en active
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855363A (en) * | 1973-08-08 | 1974-12-17 | Upjohn Co | Cycloalkane, cycloalkene, and cycloalkanone phosphonates |
| US4061697A (en) * | 1974-12-17 | 1977-12-06 | Bayer Aktiengesellschaft | Phosphorus containing flame retarding agents which are reactive with isocyanates |
Also Published As
| Publication number | Publication date |
|---|---|
| SU504781A1 (en) | 1976-02-28 |
| NL164863B (en) | 1980-09-15 |
| CH541278A (en) | 1973-09-15 |
| SU574195A1 (en) | 1977-09-30 |
| NL164863C (en) | 1981-02-16 |
| NL7004960A (en) | 1971-10-11 |
| RO62001A (en) | 1977-11-15 |
| HU162750B (en) | 1973-04-28 |
| AT300454B (en) | 1972-06-15 |
| FR2056340A5 (en) | 1971-05-14 |
| DE2022228C2 (en) | 1982-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |