DE2022228C2 - New phosphonic acid esters - Google Patents
New phosphonic acid estersInfo
- Publication number
- DE2022228C2 DE2022228C2 DE19702022228 DE2022228A DE2022228C2 DE 2022228 C2 DE2022228 C2 DE 2022228C2 DE 19702022228 DE19702022228 DE 19702022228 DE 2022228 A DE2022228 A DE 2022228A DE 2022228 C2 DE2022228 C2 DE 2022228C2
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexyl
- amine
- phosphonyl
- phosphonic acid
- radical
- 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.)
- Expired
Links
- 150000003008 phosphonic acid esters Chemical class 0.000 title claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 14
- 125000005499 phosphonyl group Chemical group 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 12
- -1 alkyl radicals Chemical class 0.000 description 12
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000780602 Senecio Species 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000009331 sowing 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
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 241000219312 Chenopodium Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000214240 Galinsoga parviflora Species 0.000 description 2
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 241000404539 Tripleurospermum Species 0.000 description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- NNGAQKAUYDTUQR-UHFFFAOYSA-N cyclohexanimine Chemical class N=C1CCCCC1 NNGAQKAUYDTUQR-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical class OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- BMZZGIWIRFMFOU-UHFFFAOYSA-N 4-cyclohexylidenebutan-1-amine Chemical compound NCCCC=C1CCCCC1 BMZZGIWIRFMFOU-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
- 244000140786 Brassica hirta Species 0.000 description 1
- 239000005630 Diquat Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 241000209048 Poa Species 0.000 description 1
- 244000292693 Poa annua Species 0.000 description 1
- 241001310793 Podium Species 0.000 description 1
- 239000002253 acid Substances 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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- MXZACTZQSGYANA-UHFFFAOYSA-N chembl545463 Chemical compound Cl.C1=CC(OC)=CC=C1C(N=C1)=CN2C1=NC(C)=C2O MXZACTZQSGYANA-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 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
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 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 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
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RPFGCUFAJAQNLJ-UHFFFAOYSA-N n-phenylcyclohexanimine Chemical compound C1CCCCC1=NC1=CC=CC=C1 RPFGCUFAJAQNLJ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-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
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fertilizers (AREA)
- Cultivation Of Plants (AREA)
Description
in der, wenn X für Wasserstoff stehtin which when X is hydrogen
R1OR 1 O
/\
R2O H / \
R 2 OH
mit N-Cyclohexylidenaminen der allgemeinen Formel with N-cyclohexylideneamines of the general formula
umsetzt, in denen Ri, R2, Ri und X die vorstehende Bedeutung besitzen.converts, in which Ri, R 2 , Ri and X have the above meaning.
3. Mittel zur Unkrautbekämpfung, dadurch gekennzeichnet, daß als wirksamer Bestandteil mindestens ein Pbosphonsäiireester der in Anspruch I definierten allgemeinen Formel enthalten ist neben oberflächenaktiven Substanzen, inerten Trägersubstanzen und Lösungsmitteln.3. Means for combating weeds, characterized in that that as an active ingredient at least one Pbosphonsäiireester in claim I defined general formula is contained in addition to surface-active substances, inert carrier substances and solvents.
Die Erfindung betrifft neue Phosphonsäureester der allgemeinen FormelThe invention relates to new phosphonic acid esters of the general formula
NH-R3 NH-R 3
gegebenenfalls durch ein o- und/oder p-Chloratom oder eine Methyl-, o-, p-Metnoxy- oder p-Nitrogruppe substituierten Phenylrest oder für einen 2-CMor-5-trifhK>rmethylrest oder für einen Benzyl- oder Cydohexylrest steht oder einen Alkylrest wie η-Butyl oder den 2-Methoxyäthylrest bedeutet oderoptionally by an o- and / or p-chlorine atom or a methyl, o-, substituted p-metnoxy or p-nitro group Phenyl radical or for a 2-CMor-5-trifhK> rmethyl radical or for a benzyl or cyclohexyl radical or an alkyl radical such as η-butyl or denotes the 2-methoxyethyl radical or
oxyphenylrest bedeutet oderoxyphenyl radical means or
2. Verfahren zur Herstellung von Phosphonsäureestern der in Anspruch I definierten allgemeinen Formel, dadurch gekennzeichnet, daß man in an sich *o bekannter Weise Phosphite der allgemeinen Formel2. Process for the preparation of phosphonic esters of the general formula defined in claim I, characterized in that phosphites of the general formula are used in a manner known per se * o
in der, wenn X für Wasserstoff steht,in which, when X is hydrogen,
is R1 und R2 Alkylreste wie Methyl bedeuten undis R 1 and R 2 are alkyl radicals such as methyl and
nenfalls durch ein o- und/oder p-Chloratom oder eine Methyl-, o-, p-Methoxy- oder o-Nitrogruppe substituierten Phenylrest oder für einen 2-Chlor-5-trifluormethylrest oder für einen Benzyl- oder Cydohexylrest steht oder einen Alkylrest wie n-Butyl oder den 2-Methoxyäthylrest bedeutet oderpossibly by an o- and / or p-chlorine atom or a methyl, o-, p-methoxy or Phenyl radical substituted by o-nitro group or for a 2-chloro-5-trifluoromethyl radical or represents a benzyl or cyclohexyl radical or an alkyl radical such as n-butyl or denotes the 2-methoxyethyl radical or
phenylrest bedeutet oderphenyl radical means or
Die neuen Phosphonsäureester werden in hohen Ausbeuten erhalten, indem man in an sich bekannter Weise Phosphite der allgemeinen FormelThe new phosphonic acid esters are obtained in high yields by being known per se Way phosphites of the general formula
R1O OR 1 OO
P
R2O HP.
R 2 OH
mit N-Cyclohexylidenaminen der allgemeinen Formelwith N-cyclohexylideneamines of the general formula
— R3 - R 3
50 umsetzt in denen Rt, R2, R3 und X die vorstehende
Bedeutung besitzen.
Die Erfindung umfaßt weiterhin Mittel zur Unkrautbekämpfung, die als Wirkstoff mindestens einen
erfindungsgemäßen Phosphonsäureester neben oberflächenaktiven Substanzen, inderten Trägersubstanzen
und Lösungsmitteln enthalten.
Die neuen Phosphonsäureester stellen Festprodukte oder öle dar, die sich in bekannten organischen
Lösungsmitteln wie zum Beispiel Alkohol, Aceton oder Benzol leicht lösen. Die Additionsreaktion kann mit den
reinen Ausgangskomponenten oder in Lösungsmitteln wie zum Beispiel Benzol, Chloroform oder Tetrachlorkohlenstoff,
gegebenenfalls unter Zugabe eines basischen Katalysators, wie zum Beispiel Triäthylamin oder
Natriumalkoholat vorgenommen werden.
Es wurde weiterhin gefunden, daß die vorstehend50 converts in which Rt, R 2 , R 3 and X have the above meaning.
The invention further comprises agents for combating weeds which contain as active ingredient at least one phosphonic acid ester according to the invention in addition to surface-active substances, inert carrier substances and solvents.
The new phosphonic acid esters are solid products or oils that dissolve easily in known organic solvents such as alcohol, acetone or benzene. The addition reaction can be carried out with the pure starting components or in solvents such as benzene, chloroform or carbon tetrachloride, optionally with the addition of a basic catalyst such as triethylamine or sodium alcoholate.
It was further found that the above
angeführten Mittel zur Unkrautbekämpfung sowohl im B e ί s ρ i e I 4
Vorauflauf als auch im Nachauflauf zur Anwendungcited means for weed control both in B e ί s ρ ie I 4
Pre-emergence and post-emergence for use
gebracht werden können. 20 Teile N-Cyclohexyl-N-O Ηί,Ο,Ο-diisopropylphospho-Die
erfindungsgemäßen Mittel können in bekannter nyl)-cyclohexyl)-amin werden in einem Gemisch, beste-Weise,
das heißt in Lösung oder auf Trägern in Form 5 hend aus 40 Teilen Xylol und 30 Teilen Methylcydoheeines
benetzbaren Pulvers, einer staubförmigen oder xanon ge!öst und mit 7 Teilen äthoxyliertem Nonylphegranulierten
Substanz oder einer Emulsion verwendet nol und 3 Teilen Caldumdodecylbenzolsulfonat verwerfen,
mischt Das entstandene homogene Emuslionskonzen-Die Darstellung benetzbarer Pulver und Emulsions- trat kann mit Wasser zu stabilen, herbizid wirkenden
konzentrate ist an sich bekannt und erfordert außer den io Spritzbrühen verdünnt werden.
Trägerstoffen oberflächenaktive Substanzen, v.ie zumcan be brought. 20 parts of N-cyclohexyl-NO Ηί, Ο, Ο-diisopropylphospho-The agents according to the invention can be in the known nyl) -cyclohexyl) -amine in a mixture, best-way, that is in solution or on carriers in the form 5 starting from 40 Parts of xylene and 30 parts of methylcydoheum, a wettable powder, a powdery or xanone ge! Ested and with 7 parts of ethoxylated nonylphegranulated substance or an emulsion used nol and 3 parts of caldumdodecylbenzenesulfonate, mixes the resulting homogeneous emulsion concentrates-The presentation of wettable powder and emulsion can Water for stable, herbicidal concentrates is known per se and requires dilution in addition to the spray liquor.
Carriers, surface-active substances, v.ie for
flüssige Trägerstoffe sind Wasser, Alkohole, aromati- 15 als vor dem Auflaufen verabreichte Herbizide wurdeLiquid carriers are water, alcohols, aromatics, when herbicides were administered before emergence
sehe Kohlenwasserstoffe, Erdölfraktionen und chlorier- dadurch ermittelt, daß Unkrautsamen in Böden ausgesätsee hydrocarbons, petroleum fractions and chlorination- determined by sowing weed seeds in the soil
te Kohlenwasserstoffe geeignet. und deren Aussaaten kurz danach oberflächig mit dente hydrocarbons. and sowing them shortly thereafter superficially with the
mit Düngemitteln oder anderen Pestiziden und Herbizi- Angewendet wurden 10 kg AS/ha als 50%iges Spritz-with fertilizers or other pesticides and herbicides - 10 kg AS / ha were used as 50% spray
den gemischt und gemeinsam ausgebracht werden. 20 pulver in 6001 Wasser/ha oder als acetonische Lösung.which are mixed and applied together. 20 powder in 6001 water / ha or as an acetone solution.
kannL Bekannte Herbizide mit vergleichbaren Wirkun- album, Galinsoga parviflora und Poa annua. DieCanL Known herbicides with comparable effectsunalbum, Galinsoga parviflora and Poa annua. the
gen wie zum Beispiel Nitro- und Cyan phenole oder auch Endauswertung erfolgte am 28. Tage nach dergenes such as nitro and cyano phenols or final evaluation took place on the 28th day after the
sieht weitaus ungünstiger. So beträgt die letale Dosis Skala mit den Noten 1 bis 9 bewertet Dabei bedeutetlooks far less favorable. Thus, the lethal dose scale is rated with grades 1 to 9
(Ratte p.o.): der Wert 1, daß 95% und mehr des Unkrautbestandes(Rat p.o.): the value 1, that 95% and more of the weed population
vernichtet sind. Der Wert 9 bedeutet keine Wirksam-are destroyed. The value 9 means no effective
loxinyl 110 mg/kg hervor. Die Nummern der Verbindungen beziehen sichloxinyl 110 mg / kg. The numbers of the connections relate
auf die Nummern in Tabelle I.
Dagegen besitzt der erfindungsgemäße Phosphon-to the numbers in Table I.
In contrast, the phosphonic acid according to the invention has
säureester N-Butyl-N-[(1-0,0-dibutylphosphonyl)-cyclo- Beispiel 6
hexyl]-amin eine LD» von 7000 mg/kg Ratte p. o. und ist 35acid ester N-Butyl-N - [(1-0,0-dibutylphosphonyl) -cyclo- Example 6
hexyl] -amine has an LD »of 7000 mg / kg rat po and is 35
gegen Warmblüter nahezu ungiftig. Die Aktivität der erfindungsgemäßen Verbindungenalmost non-toxic against warm-blooded animals. The activity of the compounds according to the invention
als nach dem Auflaufen verabreichte Herbizide wurdethan became post-emergence herbicides
_ . . . dadurch ermittelt, daß wäßrige Suspensionen oder_. . . determined by the fact that aqueous suspensions or
elsPle acetonische Lösungen auf Pflanzen, die sich im els P le acetone solutions on plants that are in
1 Mol N-Cyclohexyliden-anilin wird in einer Rührap- 40 Keimblatt- bis Zweilaubblattstadium befanden, ge-1 mole of N-cyclohexylidene-aniline is in a stirring stage.
paratur unverdünnt vorgelegt. Anschließend tropft man spritzt wurden. Angewendet wurden 4 und 10 kg AS/haparatur presented undiluted. Then drips were injected. 4 and 10 kg AS / ha were used
1 Mol Diäthylphosphit bis zum Anstieg der Reaktions- als 50%ige Spritzpulver oder acetonische Lösungen. Als1 mole of diethyl phosphite until the reaction rate rises as a 50% wettable powder or acetone solutions. as
temperatur auf 500C zu. Nachdem die Reaktionsmi- Testpflanzen dienten Sinapris arvensis, Stellaria media,temperature to 50 0 C to. After the reaction mi test plants served Sinapris arvensis, Stellaria media,
schung über Nacht stand, kann die kristalline Verbin- Senecio vuigaris, Tripleurospermum inodera, Chenopo-The crystalline compound can be found overnight, Senecio vuigaris, Tripleurospermum inodera, Chenopo-
dung verwendet werden. 45 dium album, Galinsoga parviflora, Avena sativa und Poacan be used. 45 dium album, Galinsoga parviflora, Avena sativa and Poa
annua. Die Endauswertung erfolgte am 14. Tage nachannua. The final evaluation took place on the 14th day after
R . . . 7 der Spritzung. Die Ergebnisse wurden nach einer R. . . 7th the spray. The results were after a
1 Mol N-Cyclohexyliden-butylamin und 250 ml bedeutet 1, daß 95% und mehr des Unkrautbestandes1 mole of N-cyclohexylidenebutylamine and 250 ml means 1 that 95% and more of the weed population
gehalten. Anschließend werden Benzol und Reste des auf die Nummern in Tabelle I.
Phosphites im Vakuum abdestilliert Der Phosphonsäu- 55held. Then benzene and remnants of the numbers in Table I.
Phosphites distilled off in vacuo Der Phosphonsäu- 55
reester verbleibt als öliger Rückstand. B e i s d i e I 7Reester remains as an oily residue. B e i s d i e I 7
60 selektives Verhalten (z. B. Nummer 21 und 22), das60 selective behavior (e.g. number 21 and 22) that
tritt Zur Ermittlung der nutzbaren selektiven Wirksam-occurs To determine the usable selective effective
50 Teile N-m-Methylphenyl-N-(l-(0,0-dimethylphos- keit wurden Kulturpflanzen, zum Beispiel Zuckerrüben50 parts of N-m-methylphenyl-N- (1- (0,0-dimethylphosphate) were cultivated plants, for example sugar beets
phonylcyclohexyl)-amin werden mit 40 Teilen Kaolin, 6 vor beziehungsweise nach dem Auflaufen mit denphonylcyclohexyl) amine with 40 parts of kaolin, 6 before or after emergence with the
nyl innig vermischt und in einer geeigneten Mühle AS/ha behandelt Die Spritzung erfolgte entweder kurznyl intimately mixed and treated AS / ha in a suitable mill. The spraying was either brief
vermählen. Das entstandene Spritzpulver gibt mit nach der Aussaat oder im Zwei- bis Vierblattstadium derto marry. The resulting spray powder is added after sowing or in the two- to four-leaf stage
anwendungen am 28. Tage und bei den Nachauflaufan- wurden. Beim Wert 9 wurden keine Schaden anapplications on the 28th day and post-emergence applications. At value 9 no damage was done
men. Die Ergebnisse wurden nach einer bestimmten erfindungsgemäßen Verbindung Nummer 21 in dermen. The results were obtained after a certain compound number 21 according to the invention in the
Skala mit den Noten 1 bis 9 bewertet Dabei bedeutet Nachauflaufanwendung gewonnenen Ergebnisse gehen der Wert 1, daß sämtliche Kulturpflanzen vernichtet 5 aus der Tabelle IV hervor.Scale with grades 1 to 9. Post-emergence application means that the results obtained go away the value 1, that all crops are destroyed 5 from Table IV.
Tabelle I
Allgemeine FormelTable I.
General formula
NH-R3 NH-R 3
OR2 OR 2
Beispiel Name
Nr.Example name
No.
X R1 XR 1
Fp bzw. Nj? Fp or Nj?
N-p-Oilorphenyl-N-(HO,0-dimethylphosphonyl)-cyclobexyl)-amin N-p-Oilophenyl-N- (HO, 0-dimethylphosphonyl) -cyclobexyl) -amine
N-p-Methylphenyl-N-(l-(O,O-dimethylphosphonyl)-cyclohexyl)-amin N- p -methylphenyl-N- (1- (O, O-dimethylphosphonyl) cyclohexyl) amine
H CH3 CH, H CH3 CHjH CH 3 CH, H CH 3 CHj
phosphonyl)-cyclohexyl)-aminphosphonyl) cyclohexyl amine
N-o-Methylphenyl-N-(l-(O,O-dimethylphosphonyl)-cyclohexyl)-amin N-o-methylphenyl-N- (1- (O, O-dimethylphosphonyl) -cyclohexyl) -amine
H CH3 CH3 H CH 3 CH 3
N-Phenyl-N-(HO,O-dimethylphosphonyl)- H CH3 CH3 cyclohexyl)-aminN-Phenyl-N- (HO, O-dimethylphosphonyl) -H CH 3 CH 3 cyclohexyl) -amine
phosphonyl)-cyclohexyl)-aminphosphonyl) cyclohexyl amine
phosphonyl)-cyclohexyl)-aniinphosphonyl) -cyclohexyl) -aniine
N-Benzyl-N-<HO,0-dimethylphosphonyl) H CH3 CH3 cyclohexyl)-aminN-Benzyl-N- <HO, 0-dimethylphosphonyl) H CH 3 CH 3 cyclohexyl) amine
N-p-Methoxyphenyl-N-<l-{O,O-dimethyl- H CH3 CH3 phosphonyl)-cyciohexyl)-aininNp-methoxyphenyl-N- <l- {O, O-dimethyl-H CH 3 CH 3 phosphonyl) -cyciohexyl) -ainine
N-2,4-Dichlorphenyl-N-{l-{O,O-dimethyl- H CH3 CH3 pbosphonyl>cyclohexyl>-aminN-2,4-dichlorophenyl-N- {l- {O, O-dimethyl-H CH 3 CH 3 phosphonyl>cyclohexyl> amine
N-o-Methoxyphenyl-N-(l-(0,0-dimethyl- H CH3 CH3 phosphonyl)-cyclohexyl)-aminNo-methoxyphenyl-N- (1- (0,0-dimethyl- H CH 3 CH 3 phosphonyl) -cyclohexyl) -amine
128°C128 ° C
95°C95 ° C
1060C106 0 C
NO2<f>— 191°CNO 2 <f> - 191 ° C
1.49151.4915
CH2- 1.5260CH 2 - 1.5260
1060C106 0 C
1.55111.5511
1.53781.5378
Beispiel NameExample name
Fp bzw.Fp or
12 N-4-Piperidyl-N-(HO,O-climethylphosphonyl)-cyclohexyl)-amin 12 N-4-piperidyl-N- (HO, O-climethylphosphonyl) -cyclohexyl) -amine
13 N-Phenyl-N-(l-(O,O-diäthylphosphonyl)-cyclohexyl)-amin 13 N-Phenyl-N- (1- (O, O-diethylphosphonyl) -cyclohexyl) -amine
14 N-o-Methylphenyl-N-<l-(O,O-diäthyl-14 N-o-methylphenyl-N- <l- (O, O-diethyl-
phosphonyl)-cyclohexyl)-aminphosphonyl) cyclohexyl amine
15 N-m-MethyIphenyl-N-(l-(O,O-diäthyl-15 N-m-methylphenyl-N- (l- (O, O-diethyl-
phosphooyl)-cyclohexyl)-ainin H CH3 CH3 Nphosphooyl) -cyclohexyl) -ainine H CH 3 CH 3 N
H C2H5 C2H5H C2H5 C2H5
H C2H5 C2H5 HC 2 H 5 C 2 H 5
H C2H5 HC 2 H 5
CH3 CH 3
1.49121.4912
98°C98 ° C
81°C81 ° C
CH3 P \— 1030CCH 3 P \ -103 0 C
16 N-p-MethylphenyI-N-(l-(O,O-diäthyl-16 N-p-methylphenyl-N- (l- (O, O-diethyl-
phosphonyl>cyclohexyl)-aminphosphonyl> cyclohexyl) amine
17 N-o^orphenyl-N-(l-<O,O-diäthyI-17 N-o ^ orphenyl-N- (l- <O, O-diethyI-
phosphonyl)-cyclohexyl)-aniin H C2H5 C2H5 CH3 phosphonyl) cyclohexyl) amine HC 2 H 5 C 2 H 5 CH 3
ClCl
H C2H5 C2H5 /HC 2 H 5 C 2 H 5 /
92°C92 ° C
1.5301,530
18 N-p-chloiphenyl-N-{l-(O,O-diäthyl-18 N-p-chloiphenyl-N- {l- (O, O-diethyl-
phosphonyl)-cyclohexyl)-amin H C2H5 C2H5 Cl-phosphonyl) -cyclohexyl) -amine HC 2 H 5 C 2 H 5 Cl-
1223C122 3 C
19 N-p-Methoxyphenyl-N-(l-(0,0-dichlor-19 N-p-methoxyphenyl-N- (l- (0,0-dichloro-
äthylphospbonyl)-cyclohexyl)-aminethylphosphbonyl) cyclohexylamine
680C68 0 C
20 N-Qrdohexyl-N-(l-(0,0-dichlor-20 N-hydrohexyl-N- (l- (0,0-dichloro-
ätl^lphosphonyl)-cydohexyl)-aminätl ^ lphosphonyl) -cydohexyl) -amine
1.50721.5072
N-Cydc*exyl-N-(l-(O,O-dösopropylphosphonyl)-cyclohexyl)-amin N-Cyclohexyl-N- (1- (O, O-isopropylphosphonyl) cyclohexyl) amine
methylphosphonyl)-cydohexyr)-ainm H i-C3H7 1-C3H7 < Hmethylphosphonyl) -cydohexyr) -ainm H iC 3 H 7 1-C 3 H 7 <H
ClCl
H CH3 CH3 /Ö\ F3CH CH 3 CH 3 / Ö \ F 3 C
1.7691,769
pho^»hooyI)-cyd<Aexyi)-amiiipho ^ »hooyI) -cyd <Aexyi) -amiii
älhylphosphonyl)-cyciohexyl)-ajnin C2H5 C2H5ethylphosphonyl) -cyciohexyl) -ajnine C2H5 C2H5
H i-C3H7 1-C3H7 H iC 3 H 7 1-C 3 H 7
-CH2- 1.507-CH 2 - 1,507
-CH2- 1.4966-CH 2 - 1.4966
phosphonyl)-cydohexyl)-amin H C2H5 C2H5phosphonyl) -cydohexyl) -amine H C2H5 C2H5
1.4821,482
230 244/14230 244/14
Fortsetzungcontinuation
Beispiel Name
Nr.Example name
No.
X R,X R,
Fp bzw.Fp or
N-CyclohexyI-N-(l-(0,0-diisobutyl-N-CyclohexyI-N- (l- (0,0-diisobutyl-
phosphonyl)-cyclohexyl)-amin H 1-C4H, i-C4H, < Hphosphonyl) -cyclohexyl) -amine H 1-C4H, iC 4 H, <H
1.47681.4768
N-Cyclohexyl-N-d-CO^-dipropyl-N-Cyclohexyl-N-d-CO ^ -dipropyl-
phosphonyl)-cyclohexyl)-aminphosphonyl) cyclohexyl amine
N-2-Chlorphenyl-N-(l-(0,0-diiso-N-2-chlorophenyl-N- (l- (0,0-diiso-
propylphosphonyl)-cyclohexyl)-amin H C3H7 C3H7 propylphosphonyl) cyclohexyl) amine HC 3 H 7 C 3 H 7
H i-C3H7 i-C3H7 H iC 3 H 7 iC 3 H 7
ClCl
1.4791 -1.4791 -
1.4911,491
N-Cyclohexyl-N-(HO,O-diamylphosphonyl)-cyclohexyl)-amin N-Cyclohexyl-N- (HO, O-diamylphosphonyl) -cyclohexyl) -amine
N-ßenzyl-N-d-CO.O-dichloräthylphosphonyl)-cyclohexyl)-amin N-ßenzyl-N-d-CO.O-dichloroethylphosphonyl) -cyclohexyl) -amine
1.47751.4775
H ClC2H4 ClC2H4 <f \-CH2- 1.533H ClC 2 H 4 ClC 2 H 4 <f \ -CH 2 - 1.533
N-Benzyl-N-(l-(0,0-diisobutyl-N-benzyl-N- (l- (0,0-diisobutyl-
phosphonyl)-cyclohexyl)-aminphosphonyl) cyclohexyl amine
-CH2- 1.4995-CH 2 - 1.4995
52
33
34
35
36
37
38
39
40
41
42
4352
33
34
35
36
37
38
39
40
41
42
43
N-Benzyl-N-(l-(O,O-diamylphosphonyl)-cyclohexyl)-amin N-Benzyl-N- (1- (O, O-diamylphosphonyl) -cyclohexyl) -amine
N-Butyl-N-a-(O,O-dhnethylphosphony I J-i-iN-Butyl-N-a- (O, O-dimethylphosphony I J-i-i
H C5H11H C5H11
-CH2- 1.4977-CH 2 - 1.4977
N-Butyl-N-(l-(O,O-diäthylphosphonyl)-cyclohexyl)-amin N-Butyl-N- (1- (O, O-diethylphosphonyl) -cyclohexyl) -amine
N-Butyl-N-(l-(0,0-diisopropylphosphonyl)-cyclohexyl)-aniin N-butyl-N- (1- (0,0-diisopropylphosphonyl) -cyclohexyl) -aniine
N-Butyl-N-(l-(0,0-diisobutylphosphonyl)-cyclohexyl>amin N-butyl-N- (1- (0,0-diisobutylphosphonyl) -cyclohexyl> amine
N-Butyl-N-(l-(O,O-diamylphosphonyl)-cyclohexyl)-amin N-butyl-N- (1- (O, O-diamylphosphonyl) -cyclohexyl) -amine
N-Methoxyäthyl-N-(l-(0,0-dimethylphosphQnyl)-cyGlohexyl)-amin N-methoxyethyl-N- (1- (0,0-dimethylphosphophyl) -cyGlohexyl) -amine
N-Methoxyäthyl-N-(HO,O-diisopropylphosphoayl>cyclohexyl)-amin N-methoxyethyl-N- (HO, O-diisopropylphosphoayl> cyclohexyl) amine
N-Methoxypropyl-N-(l-(O,O-diisopropylphosphonyl)-cyclohexyl)-ainin N-methoxypropyl-N- (1- (O, O-diisopropylphosphonyl) -cyclohexyl) -ainine
N-Methoxypropyl-N-(l-(0,0-diisobu1ylphosphonyi)-{yclohexyl>ainin N-methoxypropyl-N- [1- (0,0-diisobu1ylphosphonyi) - {yclohexyl> ainine
N-Methoxyäthyl-N-(l-(0,0-diisobutylphosphonyl>cyclohexyl)-amin N-methoxyethyl-N- (1- (0,0-diisobutylphosphonyl> cyclohexyl) amine
N-Methoxyälfayl-N-(l-<O,O-diamylphosphonyl)-cyclohexyl)-anun H C H3 C H3 C4H9— H C2H5 C2H.5 C4H9— I-C3K7 1-C3ri7 CJ4H9N-Methoxyalfayl-N- (l- <O, O-diamylphosphonyl) -cyclohexyl) -anun H C H3 C H3 C4H9— H C2H5 C2H.5 C4H9— I-C3K7 1-C3ri7 CJ4H9
H 1-C4H, I-C4H,- C4H,-H CsHn CsHn C4H9—H 1-C4H, I-C4H, - C 4 H, -H CsH n CsH n C 4 H 9 -
1.47101.4710
1.46201.4620
1.45651.4565
1.45971.4597
1.46301.4630
H CH3 CH3 -C2H4-OCH3 1.4708 r-C3H7 H CH 3 CH 3 -C 2 H 4 -OCH 3 1.4708 rC 3 H 7
1-C3H7 CH3O-C2H4- 1.45451-C 3 H 7 CH 3 OC 2 H 4 - 1.4545
H i-C3H7 1-C3H7 CH3O-C3H6- 1.4598 H i-C4H, 1-C4H9 CH3O-C3H4- 1.4628 H i-C«H, 1-C4H9 CH3O-C2H4- 1.4595H iC 3 H 7 1- C 3 H 7 CH 3 OC 3 H 6 - 1.4598 H iC 4 H, 1-C 4 H 9 CH 3 OC 3 H 4 - 1.4628 H iC «H, 1-C 4 H 9 CH 3 OC 2 H 4 - 1.4595
C5H11 CH3O-C2H4- 1-4625C 5 H 11 CH 3 OC 2 H 4 - 1-4625
1212th
Beispiel Name Nr.Example name no.
X R,X R,
Fp bzwFp or
N-Cyclohexyl-(HO,0-diisopropyl- CH3 i-C3H7 i-C3H7 phosphonyI)-2-methyl-cyclohexyl)-aminN-Cyclohexyl- (HO, 0-diisopropyl-CH 3 iC 3 H 7 iC 3 H 7 phosphonyI) -2-methyl-cyclohexyl) -amine
N-Butyl-N-(l-(O,O-diisobutyl- CH3 i-C4H, i-C4H, C4H9-phosphonyl)-2-methyl-cyclohexyI)-amin N-butyl-N- (1- (O, O-diisobutyl-CH 3 iC 4 H, iC 4 H, C 4 H 9 -phosphonyl) -2-methyl-cyclohexyl) -amine
1.4651,465
1.45811.4581
8 8 2 8 3 2 2 1 2 1 1 1 1 9 i 1 1 6 4 1 1 1 1 2 1 1 1 3 1 28 8 2 8 3 2 2 1 2 1 1 1 1 9 i 1 1 6 4 1 1 1 1 2 1 1 1 3 1 2
1 2 4 3 1 1 1 1 1 1 1 1 21 2 4 3 1 1 1 1 1 1 1 1 2
4 4 3 4 4 3 5 2 2 2 24 4 3 4 4 3 5 2 2 2 2
5 2 25 2 2
7 3 3 27 3 3 2
2 32 3
ι? 13ι? 13th
^ Tabelle IV ^ Table IV
';·. Nummer der Verbin- Aufwandmenge Zuckerrüben '; ·. Number of the connection application rate sugar beet
[ dung It. Tabelle I kg AS/ha[according to Table I kg AS / ha
Ü, 21 4 7 Ü, 21 4 7
i? 21 6 4i? 21 6 4
;? 21 8 2 ; ? 21 8 2
t-i 21 10 1 ti 21 10 1
Claims (1)
NH—R3 1. Phosphonic acid esters of the general formula
NH-R 3
X POR 2
XP
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD14156069 | 1969-08-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2022228A1 DE2022228A1 (en) | 1971-02-18 |
| DE2022228C2 true 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) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855363A (en) * | 1973-08-08 | 1974-12-17 | Upjohn Co | Cycloalkane, cycloalkene, and cycloalkanone phosphonates |
| DE2459491A1 (en) * | 1974-12-17 | 1976-06-24 | Bayer Ag | AGAINST ISOCYANATE-REACTIVE PHOSPHORUS FLAME RETARDANTS |
-
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 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2056340A5 (en) | 1971-05-14 |
| RO62001A (en) | 1977-11-15 |
| NL164863B (en) | 1980-09-15 |
| DE2022228A1 (en) | 1971-02-18 |
| CH541278A (en) | 1973-09-15 |
| NL164863C (en) | 1981-02-16 |
| SU504781A1 (en) | 1976-02-28 |
| SU574195A1 (en) | 1977-09-30 |
| HU162750B (en) | 1973-04-28 |
| NL7004960A (en) | 1971-10-11 |
| AT300454B (en) | 1972-06-15 |
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| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
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