DE2027772A1 - New ureas and their use to control weeds and grass weeds - Google Patents
New ureas and their use to control weeds and grass weedsInfo
- Publication number
- DE2027772A1 DE2027772A1 DE19702027772 DE2027772A DE2027772A1 DE 2027772 A1 DE2027772 A1 DE 2027772A1 DE 19702027772 DE19702027772 DE 19702027772 DE 2027772 A DE2027772 A DE 2027772A DE 2027772 A1 DE2027772 A1 DE 2027772A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- urea
- parts
- weeds
- phosphinothioyloxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 150000003672 ureas Chemical class 0.000 title claims description 14
- 241001148683 Zostera marina Species 0.000 title claims description 6
- -1 N- (diethoxy-phosphinyloxy) -N-methyl-N '- (4-bromophenyl) urea Chemical compound 0.000 claims description 39
- 239000004480 active ingredient Substances 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
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- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
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- 241000220261 Sinapis Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000002560 Solanum lycopersicum Nutrition 0.000 description 1
- 240000001949 Taraxacum officinale Species 0.000 description 1
- 235000006754 Taraxacum officinale Nutrition 0.000 description 1
- 241000245671 Taraxacum sp. Species 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- SXQXMCWCWVCFPC-UHFFFAOYSA-N aluminum;potassium;dioxido(oxo)silane Chemical compound [Al+3].[K+].[O-][Si]([O-])=O.[O-][Si]([O-])=O SXQXMCWCWVCFPC-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 235000019993 champagne Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
- IQTILSQVDUNLNB-UHFFFAOYSA-N chloro(methoxy)phosphinic acid Chemical compound COP(O)(Cl)=O IQTILSQVDUNLNB-UHFFFAOYSA-N 0.000 description 1
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 1
- FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 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
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- MNWPSRGVEDHBCF-UHFFFAOYSA-N phenoxy(propan-2-yl)carbamic acid Chemical compound C1(=CC=CC=C1)ON(C(O)=O)C(C)C MNWPSRGVEDHBCF-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
- C07F9/097—Compounds containing the structure P(=O)-O-N
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/1657—Compounds containing the structure P(=X)n-X-N (X = O, S, Se; n = 0, 1)
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2433—Compounds containing the structure N-P(=X)n-X-acyl, N-P(=X)n-X-heteroatom, N-P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/2445—Compounds containing the structure N-P(=X)n-X-acyl, N-P(=X)n-X-heteroatom, N-P(=X)n-X-CN (X = O, S, Se; n = 0, 1) containing the structure N-P(=X)n-X-N (X = O, S, Se; n = 0, 1)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
D 5a-3O72D 5a-3072
Dr. P. Zumateln ten. - Dr. E. Asemann Dr. R. Kotnigsberger - Dipl. Ph ys. R. HolzbauerDr. P. Zumateln ten. - Dr. E. Asemann Dr. R. Kotnigsberger - Dipl. Ph ys. R. Holzbauer
8 MOnchin 2, Brfluhauwlraß· 4/III8 MOnchin 2, Brfluhauwlraß 4 / III
Neue Harnstoffe und ihre Verwendung zur Bekämpfung von Unkräutern und Ungräsern New ureas and their use to control weeds and grass weeds
Die vorliegende Erfindung betrifft neue Harnstoffe, Verfahren zu ihrer Herstellung, herbizide Mittel, die als Wirkstoffe diese neuen Harnstoffe enthalten, sowie die Verwendung der neuen Wirkstoffe oder der sie enthaltenden Mittel zur Bekämpfung von Unkräutern und Ungräsern.The present invention relates to new ureas, processes for their preparation, herbicidal compositions which, as active ingredients, these contain new ureas, as well as the use of the new active ingredients or the compositions containing them for controlling weeds and grass weeds.
Die neuen Harnstoffe entsprechen der Formel I:The new ureas correspond to formula I:
-C--C-
(X)n^ ° N) - P' (I)(X) n ^ ° N) - P '(I)
R3 R 3
In dieser Formel bedeuten: · 'In this formula: '
R-, den Methyl- oder Aethylrest, R2 und R3 unabhängig voneinander je einen niederen Alkoxy- oder R, the methyl or ethyl radical, R2 and R 3 independently of one another each have a lower alkoxy or
Dialkylamino-Rest,
X einen niederen Alkyl-, Alkoxy-, Alkylthio- oder Halogen-Dialkylamino residue,
X is a lower alkyl, alkoxy, alkylthio or halogen
Alkylrest, Halogen oder die Cyanogruppe, Y Sauerstoff oder Schwefel und .n eine Zahl von 0 bis 3.Alkyl radical, halogen or the cyano group, Y oxygen or sulfur and .n a number from 0 to 3.
0Q8850/21930Q8850 / 2193
In der Formel I werden unter niederen Alkylresten X geradkettige oder verzweigte Reste mit 1 bis 4 Kohlenstoffatomen verstanden, wie Methyl, Aethyl, n-Propyl, Isopropyl, n-Butyl> see. Butyl, tert. Butyl. Solche Alkylreste bilden ebenfalls den AlkylteQ eines niederen Alkoxy-, Alkylthio-9 Halogen-alkyl- oder Dialkylaraino-Restes X, R2 und R-. Unter Halogen-alkyl werden durch Fluor, Chlor und/oder Brom substituierte niedere Alkylreste insbesondere der Tr i fluorine thy 1-Re st verstanden. Halogen steht für Fluor, Chlor, Brom und Jod.In formula I, lower alkyl radicals X are understood to mean straight-chain or branched radicals having 1 to 4 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl> see. Butyl, tert. Butyl. Such alkyl groups also form the AlkylteQ a lower alkoxy, alkylthio 9 halogen-alkyl or Dialkylaraino residue X, R 2 and R-. 1-Re are halogen-alkyl substituted by fluorine, chlorine and / or bromine-substituted lower alkyl group particularly the e Tr i fluorine thy understood st. Halogen stands for fluorine, chlorine, bromine and iodine.
Die neuen Harnstoffe der Formel I werden erfindungsgemgss hergestellt, indem man einen Hydroxy-harnstoff der Formel II:The new ureas of the formula I are according to the invention prepared by adding a hydroxy urea of formula II:
(II)(II)
(X)n
mit einem Halogenid der Formel III:(X) n
with a halide of the formula III:
Hai - P<" (III)Shark - P <"(III)
in Gegenwart einer Base und eines gegenüber den Reaktionsteilnehmern inerten Lösungs- oder Verdünnungsmittels umsetzt. In den Formeln II und III haben X, Y, Rp R2, Ro ^nd η die unter Formel I angegebenen Bedeutungen, Hai bedeutet Chlor oder Brom. Die Reaktionstemperaturen liegen jeweils zwischen -20 und 80°C. Als Basen werden tertiäre Amine, wie Trialkylamines Pyridinbasen, etc., anorganische Basen, wie Hydroxide und Carbonate von Alkali- und Erdalkalimetallen;in the presence of a base and a solvent or diluent which is inert towards the reactants. In the formulas II and III, X, Y, Rp R 2 , Ro ^ nd η have the meanings given under formula I, Hal means chlorine or bromine. The reaction temperatures are between -20 and 80 ° C in each case. Suitable bases are tertiary amines such as trialkylamines s pyridine, etc., inorganic bases such as hydroxides and carbonates of alkali and alkaline earth metals;
verwendet. Als Lösungs- oder Verdünnungsmittel kommen für das erfindungsgemässe Verfahren beispielsweise die folgenden in Betracht: aliphatische und aromatische Lösungsmittel, wie Dioxan, Tetrahydro- . furan, Ν,Ν-dialkylierte Amide, Ketone, Nitrile, Alkohole, wie Alkanole, Wasser und Gemische von organischen Lösungsmitteln mit Wasser, wie Alkohol-Wasser-»Gemische oder Chloroform-Wasser-Gemioche. Die neuen Harnstoffe der Formel I,- bei denen R2 einen Dialkylamino-Rest und R^ einen Alkoxy-Rest bedeuten» werden·. gemSss einer Variante des erfindungsgeraässen Verfahrens erhalten, isidem manused. Suitable solvents or diluents for the inventive Processes, for example, the following into consideration: aliphatic and aromatic solvents such as dioxane, tetrahydro-. furan, Ν, Ν-dialkylated amides, ketones, nitriles, alcohols, such as Alkanols, water and mixtures of organic solvents with water, such as alcohol-water mixtures or chloroform-water mixtures. The new ureas of the formula I - in which R2 is a dialkylamino radical and R ^ mean an alkoxy radical »will ·. according to a Variant of the method erfindungsgeraässen obtained, isidem one
einen Hydroxyharnstoff der Formel II mit einem Dihalogenid der Formel IV: a hydroxyurea of the formula II with a dihalide of the formula IV:
HaiShark
^ - R2 (IV)^ - R 2 (IV)
in derin the
Hai Chlor oder Brom,Shark chlorine or bromine,
Ry eine Dialkylamino-Gruppe und Ry is a dialkylamino group and
Y Sauerstoff oder Schwefel bedeuten, in einem Alkanol der Formel V IUOH worin R^ einen niederen Alkylrest bedeutet, in Gegenwart eines säurebindenden Mittels umsetzt.Y is oxygen or sulfur, in an alkanol of the formula V IUOH in which R ^ is a lower alkyl radical means, reacts in the presence of an acid-binding agent.
Die als Ausgangsstoffe ftlr das erfindungsgemässe Verfahren verwendeten bekannten Hydroxy-harnstoffe der Formel Il können nach bekannten Verfahren durch Umsetzung entsprechend substituierter Phenylisocyanate mit entsprechend substituierten Hydroxylaminen erhalten werden.The starting materials for the process according to the invention known hydroxyureas of the formula II used can be appropriately substituted by reaction according to known processes Phenyl isocyanates can be obtained with appropriately substituted hydroxylamines.
Die neuen Harnstoffe der Formel I werden nach dem erfindungsgemässen Verfahren in guten Ausbeuten und guter Reinheit erhalten. Ein Teil der Verbindungen sind kristallin, andere OeIe, sie sind in den üblichen organischen Lösungsmitteln gut löslich, schwerlöslich in Wasser und verschiedenen Kohlenwasserstoffen.The new ureas of the formula I are according to the invention Process obtained in good yields and good purity. Some of the compounds are crystalline, other oils, they are Easily soluble, sparingly soluble in common organic solvents in water and various hydrocarbons.
Die neuen Harnstoffe der Formel I besitzen ausgezeichnete herbizide Eigenschaften und können zur Bekämpfung mono- und dicotyler Unkräuter und Ungräser verwendet werden. In hohen Konzentrationen, 8-20 kg/ha, wirken die neuen Harnstoffe als Totalherbizide, in niederen, 0,5-8 „kg/ha, als selektive Herbizide. Von diesen Wirkstoffen werden schwer bekämpfbare sowie tiefwurzelnde Unkrautarten, z.B. * Leguminosen und Doldengewächse, erfasst. Ihre Applikation kann mit gleich gutem Erfolg sowohl vor dem Auflaufen (preemergence) als auch nach dem Auflaufen (postemergence) der Pflanzen erfolgen. So können Ackerunkräuter, wie z.B. Hirsearten (Panicum sp.), Sanfarten (Sinapis sp.), Gänsefussarten (Chenepodiaceae), Ackerfuchsschwanz (Alopecurus sp.) und andere Fuchsschwanzarten, z.B. Amaranthus sp., Gräser, z.B. Lolium sp., Korbbllitler, z.B. Taraxacum sp., Kamillearten (Matricaria sp.), vernichtet oder im Wachstum behindert werden, ohne dass bei Nutzpflanzen Schäden hervorgerufen werden.The new ureas of the formula I have excellent properties herbicidal properties and can be used to combat mono- and dicotyledonous Weeds and grass weeds are used. In high concentrations, 8-20 kg / ha, the new ureas act as total herbicides, in lower, 0.5-8 "kg / ha, as selective herbicides. These active ingredients include hard-to-control and deep-rooted weed species, e.g. * Legumes and umbelliferous plants, recorded. Your application can be applied with equal success both before emergence (preemergence) and also after emergence (postemergence) of the plants. So arable weeds, such as millet species (Panicum sp.), Sanf species (Sinapis sp.), Goosefoot species (Chenepodiaceae), black foxtail (Alopecurus sp.) And other foxtail species, e.g. Amaranthus sp., Grasses, e.g. Lolium sp., Asterisk, e.g. Taraxacum sp., Chamomile species (Matricaria sp.), Destroyed or hindered in growth without causing damage to crops.
009850/2193009850/2193
Die folgenden Beispiele veranschaulichen die Herstellung der * neuen Verbindungen der Formel I. Sofern nichts anderes vermerkt ist," \ sind die Temperaturen in Celsiusgraden angegeben.The following examples illustrate the production of the * new compounds of the formula I. Unless otherwise noted, "\ the temperatures are given in degrees Celsius.
Zu einer Lösung von 195 g N'-(3,4-Dichlorphenyl)-N-methyl-N-hydroxy-harnstoff und 127 ml Triethylamin in 2 Litern Benzol lässt man unter Rühren bei 10-15° 172 g Chlorrthiophosphorsäure-diäthylester, gelbst in 250 ml Benzol, langsam zutropfen. Das Reaktionsgemisch wird dann 12 Stunden bei Zimmertemperatur gerührt und anschliessend 2 Stunden bei 50 bis 60° erhitzt. Nach dem Erkalten wird der Niederschlag abfiltriert und das Filtrat am Vakuum eingeengt. Das zurückbleibende gelbe OeI wird mit Petroläther aufgekocht, mit Tierkohle gereinigt und dekantiert. Der N-(Diäthoxyphosphinothioyloxy)-N-methyl-N'-(3,4-dichlorphenyl)-harnstoff hat den Fp: 40 bis 42°.To a solution of 195 g of N '- (3,4-dichlorophenyl) -N-methyl-N-hydroxyurea and 127 ml of triethylamine in 2 liters of benzene are allowed to stir at 10-15 ° 172 g of chlorothiophosphoric acid diethyl ester, yellow in 250 ml benzene, slowly add dropwise. The reaction mixture is then stirred for 12 hours at room temperature and then Heated for 2 hours at 50 to 60 °. After cooling, the precipitate is filtered off and the filtrate is concentrated in vacuo. The remaining yellow oil is boiled with petroleum ether, cleaned with animal charcoal and decanted. The N- (diethoxyphosphinothioyloxy) -N-methyl-N '- (3,4-dichlorophenyl) urea has the mp: 40 to 42 °.
23,5 g Nl~(3,4-Dichlorphenyl)-N-methyl-N-hydroxy-harnstoff werden in 240 ml Äethanol gelöst. Die Lösung wird auf -10° gekühlt und mit 18,3 ml 6 η wässriger Natriumhydroxid-Lösung versetzt. Anschliessend werden bei gleicher Temperatur 19 g ChlorphosphorsäurediMthylester tropfenweise zugesetzt. Dann wird das Reaktionsgemisch bei Zimmertemperatur gehalten und ,nach neutraler Reaktion und negativem FeClq-Test auf Eiswasser gegossen. Der Niederschlag wird abgetrennt, mit Eiswasser gewaschen und getrocknet. Aus Methanol umkristallisiert hat der N-(Diäthoxy-phosphinyloxy)-N-methyl-Nl-<3,4-dichlor-phenyl)-harnstoff den Schmelzpunkt 111-113°.23.5 g N l ~ (3,4-dichlorophenyl) -N-methyl-N-hydroxy-urea are dissolved in 240 ml Äethanol. The solution is cooled to -10 ° and mixed with 18.3 ml of 6 η aqueous sodium hydroxide solution. Then 19 g of methyl chlorophosphate are added dropwise at the same temperature. The reaction mixture is then kept at room temperature and, after a neutral reaction and a negative FeClq test, poured onto ice water. The precipitate is separated off, washed with ice water and dried. Is recrystallized from methanol, the N- (diethoxy-phosphinyloxy) -N-methyl-N l - <3,4-dichloro-phenyl) -urea the melting point of 111-113 °.
009850/2193009850/2193
Betspiel 3Bet game 3
Zu einer Lösung von 23,5 g N'-(3,4-Dichlorphenyl)-N-methyl-N-hydroxy-harnstoff in 250 ml Aethanol lässt man unterRiihren bei 0-10° 18,33 ml 6 η Natriumhydroxid-Lösung und dann 17,82 g (Dimethylamido)-phosphoryl-dichlorid-langsam zutropfen. Man rührt eine halbe Stunde und gibt bei 5-10° weitere 16,6 ml 6 η Natriumhydroxid-Lösung tropfenweise zu. Anschliessend wird das Reaktionsgemisch bei Raumtemperatur gerührt und nach Eintreten neutraler Reaktion und negativem Ausfall des FeCl^-Testes auf Eiswasser gegossen. Der entstehende Niederschlag wird abgetrennt, mit Eiswasser gewaschen und getrocknet. Nach dem Umkristallisieren aus Aethanol erhält man den N-(Aethoxy-dimethylamino-phosphinyloxy)-N-methyl-N'-(3,4-dichlorphenyl)-harnstoff mit dem Schmelzpunkt: 96-98°.To a solution of 23.5 g of N '- (3,4-dichlorophenyl) -N-methyl-N-hydroxyurea 18.33 ml of 6 η sodium hydroxide solution and then 17.82 g of (dimethylamido) phosphoryl dichloride are slowly left in 250 ml of ethanol with stirring at 0-10 ° drip. The mixture is stirred for half an hour and a further 16.6 ml of 6 η sodium hydroxide solution are added at 5-10 ° drop by drop. The reaction mixture is then stirred at room temperature and, after the occurrence of a neutral reaction, and Poured negative result of the FeCl ^ -Test on ice water. The emerging Precipitate is separated off, washed with ice water and dried. After recrystallization from ethanol one obtains the N- (ethoxy-dimethylamino-phosphinyloxy) -N-methyl-N '- (3,4-dichlorophenyl) urea with the melting point: 96-98 °.
Zu einer Suspension von 24,5 g N'-(4-Bromphenyl)-N-methyl-N-hydroxy-harnstoff in 300 ml Methylenchlorid und 150 ml Wasser lässt man unter Rühren bei 20-25° 16,7 ml 6n Natronlauge und anschliessend 14,5 g PhosphorsMure-dimethylester-chlorid zutropfen, und man rührt 1 Stunde bei Raumtemperatur. Nach Eintreten neutraler Reaktion und negativem Ausfall des FeClo-Testes wird die organische Phase abgetrennt, mit Wasser gewaschen und über Natriumsulfat getrocknet. Der nach dem Eindampfen des Methylenchlorids zurückbleibende kristalline Rückstand wird aus Benzol umkristallisiert. Das erhaltene N-(Dimethoxy-phosphinyloxy)-N-methyl-N'-(4-brom-phenyl)-harnstoff hat den Fp. 135-37°.To a suspension of 24.5 g of N '- (4-bromophenyl) -N-methyl-N-hydroxyurea in 300 ml of methylene chloride and 150 ml of water, 16.7 ml of 6N sodium hydroxide solution and then left with stirring at 20-25 ° 14.5 g of phosphorus murine dimethyl ester chloride are added dropwise, and the mixture is stirred for 1 hour at room temperature. After entering, more neutral Reaction and negative failure of the FeClo test is the organic Phase separated, washed with water and dried over sodium sulfate. The crystalline residue remaining after evaporation of the methylene chloride is recrystallized from benzene. That obtained N- (dimethoxy-phosphinyloxy) -N-methyl-N '- (4-bromophenyl) urea has a melting point of 135-37 °.
Nach den in den vorangehenden Beispielen beschriebenen Methoden wurden unter Verwendung der entsprechenden Menge Hydroxy-phenylharnstoff und Phosphorhalogenid die in der folgenden Tabelle auf- ' geführten Verbindungen der Formel I hergestellt.According to the methods described in the preceding examples, using the appropriate amount of hydroxyphenylurea and phosphorus halide, the compounds of the formula I listed in the following table were prepared.
009850/2193009850/2193
Tabelle ϊTable ϊ
u 7 -u 7 -
• ο ■ >• ο ■>
Nr.example
No.
DatenPhysical
data
39
40
41
42
43
44
45
46
4738 ·
39
40
41
42
43
44
45
46
47
chlor-4-methoxy-phenyl)-harnstoff
N-(Diäthoxy-phosphinothioyloxy)-N-methyl-
N'-(3-chlor-4-methoxy-phenyl)-harnstoff
N-(Dimethoxy-phosphinyloxy)-N-methyl-N'-
(3-chlor-4-methy1-phenyl)-harnstoff
N-(Dimethoxy-phosphinothioyloxy)-N-methyl-
N'-(3-chlor-4-methyl-phenyl)-harnstoff
N-(Diäthoxy-phosphinyloxy)-N-methyl-N'-
(3-chlor-4-methy1-phenyl)-harnstoff
N-(Diäthoxy-phosphinothioyloxy)-N-methyl-
N!-(3-chlor-4-methyl-phenyl)-harnstoff
N-(Dimethoxy-phosphinyloxy)-N-methyl-N'-
(3-methyl-4-brom-phenyl)-harnstoff
N-(Dimethoxy-phosphinothioyl)-N-methyl-
N'-(3-methyl-4-brom-phenyl)-harnstoff
N-(Diäthoxy-phosphinyloxy)-N-methyl-N'-
(3-methyl»4-brom-phenyl)-harnstoff
N-(Diäthoxy-phosphinothioyloxy)-N-methyl-
N'-(3-methyl-4-brom-phenyl)-harnstoffN- (diethoxy-phosphinyloxy) -N-methyl-N '- (3-
chloro-4-methoxyphenyl) urea
N- (diethoxy-phosphinothioyloxy) -N-methyl-
N '- (3-chloro-4-methoxyphenyl) urea
N- (Dimethoxy-phosphinyloxy) -N-methyl-N'-
(3-chloro-4-methy1-phenyl) urea
N- (Dimethoxy-phosphinothioyloxy) -N-methyl-
N '- (3-chloro-4-methyl-phenyl) urea
N- (diethoxy-phosphinyloxy) -N-methyl-N'-
(3-chloro-4-methy1-phenyl) urea
N- (diethoxy-phosphinothioyloxy) -N-methyl-
N! - (3-chloro-4-methyl-phenyl) -urea
N- (Dimethoxy-phosphinyloxy) -N-methyl-N'-
(3-methyl-4-bromophenyl) urea
N- (Dimethoxy-phosphinothioyl) -N-methyl-
N '- (3-methyl-4-bromophenyl) urea
N- (diethoxy-phosphinyloxy) -N-methyl-N'-
(3-methyl »4-bromophenyl) urea
N- (diethoxy-phosphinothioyloxy) -N-methyl-
N '- (3-methyl-4-bromophenyl) urea
Fp. 7O-72°C
Fp. 89-91°C
Fp, 66-670C
Fp. 86-880C
Fp. 56-58°C
Fp. 110-1130C
Fp. 98-10O0C
Fp. 52-54°CM.p. 82-84 ° C
M.p. 70-72 ° C
M.p. 89-91 ° C
Mp, 66-67 0 C
Mp. 86-88 0 C
Mp 56-58 ° C
Mp. 110-113 0 C
Mp. 98-10O 0 C
Mp 52-54 ° C
009850/2193009850/2193
Die herbizide Wirkung der neuen Harnstoffe wird durch die folgenden Versuche verdeutlicht:The herbicidal effect of the new ureas is illustrated by the following experiments:
1·. Vorauflauf-Versuch mit eingesäten Testpflanzen 1·. Pre-emergence experiment with sown test plants
Der Wirkstoff wird als 10%iges Pulverkonzentrat in einer Konzen-The active ingredient is supplied as a 10% powder concentrate in a concentrate
tration von 1 g Wirkstoff pro m Erde(l cm Erdschicht) in Gartenerde eingearbeitet, diese in Saatschalen eingefüllt, Die Saatschalen werden mit folgenden Testpflanzen eingesät;Tration of 1 g of active ingredient per m of soil (1 cm layer of soil) in garden soil incorporated, these are filled into seed trays. The seed trays are sown with the following test plants;
Hafer (Avena sativa),Oats (Avena sativa),
Senf (Sinapis arvensis),Mustard (Sinapis arvensis),
italienisches Raygras (Lolium multiflorum), Tomate (Solanum lycopersicum),Italian ryegrass (Lolium multiflorum), Tomato (Solanum lycopersicum),
Hirse (Setaria italica),Millet (Setaria italica),
und dann im Gewächshaus bei 20 - 24° und 70% relativer Luftfeuchtigkej.t unter Tageslicht gehalten. Die Auswertung des Versuches erfolgte nach 20 Tagen. Die Bonitierung wird nach dem 10er Index vorgenommen :.-■■-■and then in a greenhouse at 20 - 24 ° and 70% relative humidity kept under daylight. The test was evaluated after 20 days. The rating is carried out according to the 10 index : .- ■■ - ■
10 : Pflanzen ungeschädigt = Kontrolle 0 : Pflanzen abgestorben
9-1 : Zwischenstufen"der Schädigung10: Plants undamaged = control 0: Plants dead
9-1: Intermediate stages of damage
Das 10%ige PulverrKonzentrat hat die folgende Zusammensetzung: 10 Teile Wirkstoff? 0,6 Teile Dibutylnaphttalinsulfon- .. säure-Natrium-Sals, 1 Teil Naphthalinsulfonsäuren-Phenolsulfonsäuren-Formaldehyd-Kondensat (3:2:1), IQ Teile Natrium-Alurainium-Silikat und 78,4 Teile Kaolin.The 10% powder concentrate has the following composition: 10 parts of active ingredient ? 0.6 parts of dibutylnaphthalenesulfonic acid-sodium sals, 1 part naphthalenesulfonic acids-phenolsulfonic acids-formaldehyde condensate (3: 2: 1), 1Q parts sodium-alurainium-silicate and 78.4 parts kaolin.
009850/2193009850/2193
Beispiel Nr.Active ingredient
Example no.
OOS850/21S3OOS850 / 21S3
1. Herbizide Wirkung bei Applikation der Wirkstoffe nach dem Auflaufen1. Herbicidal effect when the active ingredients are applied after emergence
der Testpflanzenof the test plants
In Plastiktöpfen werden als Testpflanzen Hafer (Avena sativa) und Senf (Sinapis alba) herangezogen. Im 2-4-Blattstadium werden die Pflanzen mit einer 2%igen Wässrigen Wirkstoffemulsion (erhalten aus einem 25%igen emulgierbaren Konzentrat) in einer Konzentration entsprechend 5 kg Wirkstoff pro Hektar behandelt und anschliessend bei 25 - 28° und 40 - 507» relativer Luftfeuchtigkeit unter Tageslicht gehalten. Nach 7 Tagen wird der Versuch ausgewertet. Die Bonitierung erfolgt nach dem 10er Index:Oats (Avena sativa) and mustard (Sinapis alba) are used as test plants in plastic pots. In the 2-4 leaf stage, the Plants with a 2% aqueous active substance emulsion (obtained from a 25% emulsifiable concentrate) in a concentration corresponding to 5 kg of active ingredient per hectare treated and then added 25 - 28 ° and 40 - 507 »relative humidity under daylight held. The experiment is evaluated after 7 days. The rating is based on the 10 index:
10 « Pflanzen unbeschädigt (Kontrolle) i 10 «Plants undamaged (control) i
9-1 β Zwischenstufen der Schädigung 0 ■ Pflanzen abgestorben9-1 β intermediate stages of damage 0 ■ Plants dead
Das emulgierbare Konzentrat hat die folgende Zusammensetzung: 25 Teile Wirkstoff, 32,5 Teile Isophoron (3,5,5-Trimethyl-2-cyclohexen-l-on), 32,5 Teile Methyläthylketon, 10 Teile eines Kombinationsemulgators, einer Mischung aus NonylphenolpolyoxySthylen und Calcium-dodecylbenzol-sulfonat.The emulsifiable concentrate has the following composition: 25 parts of active ingredient, 32.5 parts of isophorone (3,5,5-trimethyl-2-cyclohexen-l-one), 32.5 parts of methyl ethyl ketone, 10 parts of a combination emulsifier, a mixture of NonylphenolpolyoxySthylen and calcium dodecylbenzene sulfonate.
009850/2193009850/2193
Vergleichssubstanzen (bekannt aus dem südafrikanischen PatentComparative substances (known from the South African patent
Nr. 67/4170)No. 67/4170)
CH3 - N'CH 3 - N '
.CONH -
0 CONH-CH,.CONH -
0 CONH-CH,
Haferoats
Senfmustard
CH3 - N.CH 3 - N.
CONH - C CONH - C
OCON(CTOCON (CT
CH3 - NCH 3 - N
1010
Q098SC '2133Q098SC '2133
3. Nachauflauf-Versuch mit eingesäten Unkrautern: 3. Post-emergence attempt with sown weeds:
In Saatschalen werden als Testpflanzen Weizen (Kulturpflanze), Chenopodium album, Sinapis arvensis, Polygonum convolvulus, PoIygonum persicaria, Atriplex, Hirse und Capsella bursa pastoris eingesät. Im 4-Blatt-Stadium werden die Pflanzen mit einer 270igen wässrigen Emulsion besprüht. Anschliessend werden die Pflanzen bei 25-28° und 40-50% relativer Luftfeuchtigkeit unter Tageslicht gehalten. Wheat (crop), Chenopodium album, Sinapis arvensis, Polygonum convolvulus, Polygonum persicaria, Atriplex, millet and Capsella bursa pastoris are sown in seed trays as test plants. At the 4-leaf stage, the plants are sprayed with an aqueous emulsion 27 0. The plants are then kept under daylight at 25-28 ° and 40-50% relative humidity.
Die Auswertung des Versuches erfolgte nach 8 Tagen (A) und nach 18 Tagen (B), die Beurteilung nach dem 10er Index:The evaluation of the experiment took place after 8 days (A) and after 18 days (B), the assessment according to the 10 index:
10 = Pflanzen unbeschädigt »Kontrolle 0 = Pflanzen abgestorben
9-1 = Zwischenstufen der Schädigung10 = plants undamaged »control 0 = plants dead
9-1 = intermediate stages of damage
Die 2%ige wässrige Emulsion wurde durch Verdünnen mit Wasser aus einem 25% emulgierbaren Konzentrat folgender Zusammensetzung erhalten: 25 Teile Wirkstoff, 32,5 Teile Isophoron, 32,5 Teile Methyläthylketon, 10 Teile eines Kombinationsemulgators, bestehend aus Nonylphenolpolyoxyäthylen und Dodecylbenzolsulfonsäure-Calcium Salz.The 2% aqueous emulsion was made by diluting with water from a 25% emulsifiable concentrate of the following composition obtained: 25 parts of active ingredient, 32.5 parts of isophorone, 32.5 parts of methyl ethyl ketone, 10 parts of a combination emulsifier, consisting from nonylphenol polyoxyethylene and dodecylbenzenesulfonic acid calcium Salt.
Bei dem als Kulturpflanze mitgeführten Weizen zeigten sich nur schwache aber reversible Schädigungen nach 18 Tagen.In the case of the wheat carried as a crop plant, only slight but reversible damage was found after 18 days.
00 9850/219300 9850/2193
O) noO) no
O O OO O O
CVJ CSJ —CVJ CSJ -
·— ο ca· - ο approx
O.O.
ca ο οca ο ο
ι cι c
C OC O
O ο οO ο ο
IOIO
•— fr) tn• - fr) tn
X -CX -C
*+·* Οί-Ο l_ C= O* + * Οί-Ο l_ C = O
ä pä p
0 9 8 5 0 / 2 1 90 9 8 5 0/2 1 9
4- Wirkung auf eingesäte Unkräuter bei Applikation nach dem Auflaufen der Pflanzen im Freiland; 4- Effect on sown weeds when applied after the plants have emerged in the field;
In ein vorbereitetes Saatbeet wurden folgende Unkräuter eingesät: Sinapis alba, Amaranthus spez., Galium aparine, Taraxacum off icinalis und Loliuro multiflora. Sowie die Pflanzen 5 bis 15 cm gross sind (je nach Pflanzenart), werden sie mit einer wässrigen Emulsion der Wirkstoffe besprüht. 18 Tage nach der Behandlung wird die Beurteilung der Wirkung nach dem logarithmischen Index vorgenommen:The following weeds were sown in a prepared seed bed: Sinapis alba, Amaranthus spec., Galium aparine, Taraxacum off icinalis and Loliuro multiflora. As well as plants 5 to 15 cm in size (depending on the type of plant), they are sprayed with an aqueous emulsion of the active ingredients. 18 days after treatment the assessment of the effect is carried out according to the logarithmic index:
1 « 1007oige Wirkung auf eingesäte Unkräuter 4 = 90%ige Wirkung auf eingesäte Unkräuter 9 = keine Wirkung.1 «1007o effect on sown weeds 4 = 90% effect on sown weeds 9 = no effect.
Die wässrige Emulsion wurde durch Verdünnen mit Wasser aus einem 25%igen emulgierbaren Konzentrat folgender Zusammensetzung erhalten: 25 Teile Wirkstoff, 5 Teile eines Kombinationsemulgators bestehend aus Nonylphenolpolyoxyathylen und Dodecylbenzolsulfonsäure-Calcium-Salz, 67,5 Teile Xylol und 2,5 Teile Epichlorhydrin.The aqueous emulsion was made up by diluting it with water a 25% emulsifiable concentrate of the following composition was obtained: 25 parts of active ingredient, 5 parts of a combination emulsifier consisting of nonylphenol polyoxyethylene and dodecylbenzenesulfonic acid calcium salt, 67.5 parts of xylene and 2.5 parts of epichlorohydrin.
C GS? ^r-C GS? ^ r-
Zur Herstellung von herbiziden Mitteln werden die Wirkstoffe mit geeigneten Trägerstoffen und/oder Verteilungsmitteln vermischt, Zur Verbreiterung des Wirkungsspektrums kann man diesen Mitteln noch andere Herbizide zumischen, beispielsweise aus der Reihe der Triazine, wie Halogen-diamino-s-triazine, Alkoxy- und Alkylthiodiamino-s-triazine, Triazole, Diazine, wie Uracile, aliphatische Carbonsäuren und Halogencarbonsäuren, halogenierte Benzoesäuren und Phenylessigsäuren, Aryloxyalkancarböns'ciur en, Hydrazide, Amide, Nitrile, Ester solcher Carbonsäuren, Carbaminsäure- und Thiocarbaminsäureester, Harnstoffe etc.For the production of herbicidal agents, the active ingredients are mixed with suitable carriers and / or distribution agents, To widen the spectrum of action one can use these means Mix in other herbicides, for example from the series of triazines, such as halo-diamino-s-triazines, alkoxy- and alkylthiodiamino-s-triazines, Triazoles, diazines, such as uracils, aliphatic carboxylic acids and halocarboxylic acids, halogenated benzoic acids and phenylacetic acids, aryloxyalkanecarbones, hydrazides, amides, Nitriles, esters of such carboxylic acids, carbamic and thiocarbamic esters, ureas, etc.
Vertreter solcher beitnischbaren herbiziden Wirkstoffe sind z.B. folgende Verbindungen:Representatives of such herbicidal active ingredients which can be mixed in are e.g. the following connections:
2-Chlor-4,6-bis-(älhylamino)-s-triazin, 2-Chlor-4-äthylamino-6-isopropyleinino-s-triazin, 2-Methoxy-4,6-bis-(isopropylamino)-s-triazin, 2-Diäthylairiino-4-isopropylacetaniido-6-methoxy-s-triazin, 2~Isopropylamino-4-methoxypropylamino-6-methylthio-s-triazin, 2-llethylthio.-4,6-bis-(isopropylamino)-s-l:riazin, 2-Methylthio-456-bis-(äthylamino)-s-üriazin, 2-Methylt:hio-4-ythylamino-6-isopropylamino-s-triazin, 2-Methoxy-4-ät.hy]amino-6-isopropylainino-s-l:riazin, 2-Mothoxy-4,6-bis-Oithylamino)-s-triazin, 2-ChIor-43f>-bi s-(isopropylamino)-s-triazin, Dinitro-sec.bufy!phenol und seine Salze, Pentachlorphenol und seine Salze, Tric.hloressijrr.iiure und deren Salze, 2,2-Dichlorpropionsäure und deren Salze, ?- ChI or -Ii ,H-di a 1 IyI essi gsäureamid, MalßinsUm-o-hydrazid,2-chloro-4,6-bis- (älhylamino) -s-triazine, 2-chloro-4-ethylamino-6-isopropylinino-s-triazine, 2-methoxy-4,6-bis- (isopropylamino) -s- triazine, 2-diethylairiino-4-isopropylacetaniido-6-methoxy-s-triazine, 2-isopropylamino-4-methoxypropylamino-6-methylthio-s-triazine, 2-methylthio-4,6-bis (isopropylamino) -sl : riazine, 2-methylthio-4 5 6-bis- (ethylamino) -s-uriazine, 2-methylt: hio-4-ethylamino-6-isopropylamino-s-triazine, 2-methoxy-4-ät.hy] amino -6-isopropylamino-sl: riazine, 2-mothoxy-4,6-bis-ethylamino) -s-triazine, 2-chloro-4 3 f> -bi s- (isopropylamino) -s-triazine, dinitro-sec. bufy! phenol and its salts, pentachlorophenol and its salts, tric.hloressijrr.iiure and its salts, 2,2-dichloropropionic acid and its salts, hydrazide,
2,3,6-Trichlorbenzoesäure und deren SaIsP1 ?,3,5,6-Ti.« rachJcrbensoesaure und deren Salre, 2-M(M:hoxy-3,5,6-t.r5.chloi:benzoesaure und deren Salze, ih3,rv..ii* :h1m benzoesäure und deren Salze,2,3,6-Trichlorobenzoic acid and its SaIsP 1 ?, 3,5,6-Ti. «RachJcrbensoesaure and its Salre, 2-M (M: hoxy-3,5,6-t.r5.chloi: benzoic acid and its Salts, ih3, rv..ii * : h1m benzoic acid and its salts,
:> · ί η-.'..: '■ --nvoesäure und deren SnI^e1 ■--i4 chi oi !-^-ticesStire und deren Sa)xe, 0 08850/2193 : > · Ί η -. '..:' ■ --nvoic acid and its SnI ^ e 1 ■ --i 4 chi oi! - ^ - ticesStire and its Sa) xe, 0 08850/2193
2-Methyl-3,6-dichlorbenzoesäure und deren Salze, 2,6-Dichlorbenzonitril,2-methyl-3,6-dichlorobenzoic acid and its salts, 2,6-dichlorobenzonitrile,
2,6-Dichlor-thiobenzamid,2,6-dichloro-thiobenzamide,
2,3,6-Trichlorphenylessigsäure und deren Salze, 2,4-Dichlorphenoxyessigsäure und deren Salze, 2,4,5-Trichlorphenoxyessigsäure, deren Salze und Ester, (2-Methyl-4-chlorphenoxy)-essigsäure, deren Salze und Ester, 2-(2,4,5-Trichlorphenoxy)-propionsäure, deren Salze und Ester, 2-(2,4,5-Trichlorphenoxy)-äthyl-2,2-dichlorpropionat, 4-(2,4-Dichlorphenoxy)-buttersäure, deren Salze und Ester, 4-(2-Methyl-4-chlorphenoxy)-buttersäure, deren Salze und Ester, 2,3,6-Trichlorbenzyloxypropanol, 4-Amino-3,5,6-trichlorpicolinsäure,2,3,6-trichlorophenylacetic acid and its salts, 2,4-dichlorophenoxyacetic acid and its salts, 2,4,5-trichlorophenoxyacetic acid, its salts and esters, (2-methyl-4-chlorophenoxy) acetic acid, its salts and esters, 2- (2,4,5-trichlorophenoxy) propionic acid, its salts and esters, 2- (2,4,5-trichlorophenoxy) -ethyl-2,2-dichloropropionate, 4- (2,4-dichlorophenoxy) butyric acid, its salts and esters, 4- (2-methyl-4-chlorophenoxy) butyric acid, their salts and esters, 2,3,6-trichlorobenzyloxypropanol, 4-amino-3,5,6-trichloropicolinic acid,
N'-Cyclooctyl-NjN-dimethyl-harnstoff, 3-Phenyl-l,1-dimethyl-harnstoff,N'-Cyclooctyl-NjN-dimethyl-urea, 3-phenyl-l, 1-dimethyl urea,
3-(4'-Chlorphenyl)-!,1-dimethyl-harnstoff, 3-(3'-Trifluormethylphenyl)-l,1-dimethyl-harnstoff, 3-(3',4'-Dichlorphenyl)-1,1-dimethyl-harnstoff, 3-(3 ' ,4l-Dichlorphenyl)-l-n-butyl-l-methyl-harnstoff, 3-(3f,4!-Dichlorphenyl)-l,l,3-trimethyl-harnstoff, 3-(3',4'-Dichlorphenyl)-1,1-diäthyl-harnstoff, 3-(4'-Chlorphenyl)-l-methoxy-l-methyl-harnstoff, 3-(3 ' ,4 I-Dichlorphenyl)-:l-methoxy-l-methyl-harnstoff, 3-(4'-Bromphenyl)-l-methoxy-l-methyl-harnstoff, ■ . ' 3-(3',4'-Dichlorphenyl)-3-methoxy-l,1-dimethyl-harnstoff, 3-(4'-Chlorphenoxyphenyl)-l,l-dimethyl-harnstoff, N,N-Di-(n-propyl)-S-äthyl-thiocarbaminsäureester, N,N-Di-(n-propyl)-S-n-propyl-thiocarbaminsäureester, . · N-Aethyl-N-(η-butyl)-S-n-propyl-thiocarbaminsäureester,,3- (4'-chlorophenyl) - !, 1-dimethyl-urea, 3- (3'-trifluoromethylphenyl) -l, 1-dimethyl-urea, 3- (3 ', 4'-dichlorophenyl) -1,1- dimethyl urea, 3- (3 ', 4 l -dichlorophenyl) -ln-butyl-l-methyl-urea, 3- (3 f , 4 ! -dichlorophenyl) -l, l, 3-trimethyl urea, 3- (3 ', 4'-dichlorophenyl) -1,1-diethyl urea, 3- (4'-chlorophenyl) -l-methoxy-1-methyl-urea, 3- (3', 4 I -dichlorophenyl) -: l-methoxy-l-methyl-urea, 3- (4'-bromophenyl) -l-methoxy-l-methyl-urea, ■. ' 3- (3', 4'-dichlorophenyl) -3-methoxy-l, 1-dimethyl-urea, 3- (4'-chlorophenoxyphenyl) -l, l-dimethyl-urea, N, N-di- (n -propyl) -S-ethyl-thiocarbamic acid ester, N, N-di- (n-propyl) -Sn-propyl-thiocarbamic acid ester,. · N-Aethyl-N- (η-butyl) -Sn-propyl-thiocarbamic acid ester ,,
N-Phenyl-O-isopropyl-carbaminsäureester, . ■...N-phenyl-O-isopropyl-carbamic acid ester,. ■ ...
N-(m-Chlorphenyl)-0-isopropyl-carbaminsäureester, ■■,. . .N- (m-chlorophenyl) -0-isopropyl-carbamic acid ester, ■■ ,. . .
N-(m-Chlorphenyl)-0-4-chlor-butin-(2)-yl-carbaminsäureester, ■N- (m-Chlorophenyl) -0-4-chloro-butyn- (2) -yl-carbamic acid ester, ■
N-(3l,4l-Dichlorphenyl)-0-methyl-carbaminsäureester. "N- (3 l , 4 l -dichlorophenyl) -0-methyl-carbamic acid ester. "
009850/2193009850/2193
Die Herstellung erfindungsgemässer herbizider Mittel erfolgt in an sich bekannter Weise durch inniges Vermischen und Vermählen von Wirkstoffen der allgemeinen Formel I mit geeigneten Trägerstoffen, gegebenenfalls unter Zusatz von gegenüber den Wirkstoffen inerten Dispersions- oder Lösungsmitteln. Die Wirkstoffe können in den folgenden Aufarbeitungsformen vorliegen und angewendet werden: The herbicidal compositions according to the invention are produced in a manner known per se by intimate mixing and grinding of active ingredients of the general formula I with suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active ingredients. The active ingredients can are available and used in the following processing forms:
feste Aufarbeitungsformen: Staubemittel, Streumittel, Granulate, ümhlillungsgranulate, Imprägnierungsgranulate und llomogengranulate;
in Wasser dispergierbare Wirkstoffkonzentrate: SpritzpulverSolid forms of processing: dusting agents, scattering agents, granulates, milling granulates, impregnation granulates and homogeneous granulates;
Active substance concentrates dispersible in water: wettable powder
(wettable powder), Fasten, Emulsionen; flüssige Aufarbeitungsformen: Lösungen, Aerosole. λ (wettable powder), fasting, emulsions; Liquid processing forms: solutions, aerosols. λ
Zur Herstellung fester Aufarbeitungsformen (Staubemittel, Streumittel, Granulate) werden die Wirkstoffe mit festen Träger Stoffen vermischt. Die Korngrösse der Trägerstoffe beträgt für Stäubemittel ca. 0,075 bis 0,2 mm und für Granulate 0,2 mm oder mehr. Die Wirkstoffkonzentrationen in den festen Aufarbeitungsformen betragen in der Regel 0,5 bis 90 % besonders 1,0 bis 80 %. Diesen Gemischen können ferner den Wirkstoff stabilisierende Zusätze und/oder nichtionische, anionenaktive und kationenaktive Stoffe zugegeben werden, die beispielsweise die Haftfestigkeit der Wirkstoffe auf Pflanzen und Pflanzenteilen verbessern (Haft- und Klebemittel) und/oder eine bessere Benetzbarkeit (Netzmittel) sowie Dispergierbarkeit (Dispergatoren) gewährleisten.For the production of solid processing forms (dusting agents, grit, granulates) the active ingredients are mixed with solid carriers. The grain size of the carrier materials is approx. 0.075 to 0.2 mm for dusts and 0.2 mm or more for granulates. The active ingredient concentrations in the solid working-up forms are generally 0.5 to 90 %, particularly 1.0 to 80 %. These mixtures can also be added to the active ingredient stabilizing additives and / or nonionic, anion-active and cation-active substances, which, for example, improve the adhesion of the active ingredients to plants and parts of plants (adhesives and adhesives) and / or better wettability (wetting agents) and dispersibility (dispersants ) guarantee.
In Wasser dispergierbare Wirkstoffkonzentrate, Spritzpulver (wettable powder), Pasten und Emulsionskonzentrate stellen Mittel dar, die mit Wasser auf jede gewünschte Konzentration verdünnt werden können. Sie bestehen aus Wirkstoff, Trägerstoff, gegebenenfalls den Wirkstoff stabilisierenden Zusätzen, oberflächenaktiven Substanzen und Antischaummitteln und gegebenenfalls Lösungsmitteln. Die Wirkstoff konzentration in diesen Mitteln beträgt 5-807o. Die Spritzpulver (wettable powder) und Pasten werden erhalten, indem man die Wirkstoffe wit Dispergiermitteln und pulverförrnigen Tragerstoffen in geeigneten Vorrichtungen bis zur Homogenität vermischt und vermählt. In isianchen Fällen i;t es; vorteilhaft, MischungenActive ingredient concentrates dispersible in water, wettable powders, pastes and emulsion concentrates are agents which can be diluted with water to any desired concentration. They consist of active ingredient, carrier, optionally additives stabilizing the active ingredient, surface-active substances and antifoams and optionally solvents. The active ingredient concentration in these agents is 5-807 o . The wettable powders and pastes are obtained by mixing and grinding the active ingredients with dispersants and powdery carriers in suitable devices until homogeneous. In other cases it is; advantageous mixtures
00985 0/219300985 0/2193
verschiedener Trägers toff e zu verwenden. Als Antischaummittel korn men zum Beispiel Silicone usw. in Frage. Die Wirkstoffe werden mit den oben aufgeführten Zusätzen so vermischt, vermählen, gesiebt und passiert, dass bei Spritzpulvern der feste Anteil eine Korngrösse von 0,02 bis 0,04 und bei Pasten von 0,003 mm nicht überschreitet. Zur Herstellung von Emulsionskonzentraten und Pasten werden Dispergiermittel, organische Lösungsmittel und Wasser verwendet. Die Lösungsmittel müssen praktisch geruchlos, nicht phytotoxisch, den Wirksteffen gegenüber inert und dürfen nicht leicht brennbar sein.different carriers to be used. As an antifoam grain men, for example, silicones etc. in question. The active ingredients are with the additives listed above are mixed, ground, sieved and happens that in wettable powders the solid portion does not exceed a grain size of 0.02 to 0.04 and in pastes of 0.003 mm. For the production of emulsion concentrates and pastes, dispersants, organic solvents and water are used. The solvents must be practically odorless, not phytotoxic Effective strengths are inert towards and must not be easily flammable.
Ferner kcinnen die erfindungsgemessen Mittel in Form von Lösungen angewendet werden. Hierzu wird der Wirkstoff bzw. werden mehrere Wirkstoffe der allgemeinen Formel I in geeigneten organischen Lösungsmitteln, Lösungsmittel gemischen oder Wasser gelöst. Dia Lösungen sollen die Wirkstoffe in einem Konzentrationsbereich von 10 - 30% enthalten. Den beschriebenen Mitteln lassen sich andere biozide Wirkstoffe oder Mittel beimischen. So können die neuen Mittel ausser den genannten Verbindungen der allgemeinen Formel I und anderen Herbiziden, z.B. Insektizide, Fungizide, Bakterizide, Fungistatika, Bakteriostatika oder Nematozide zur Verbreiterung des Wirkungsspektruns enthalten.Furthermore, the agents according to the invention can be in the form of Solutions are applied. To do this, the active ingredient will be or several active ingredients of general formula I in suitable organic Solvents, mixed solvents or dissolved in water. Dia solutions are intended to contain the active ingredients in a concentration range from 10 - 30% included. Other biocidal active ingredients or agents can be admixed with the agents described. So they can new means besides the mentioned compounds of general Formula I and other herbicides, e.g. insecticides, fungicides, bactericides, Fungistats, bacteriostats or nematocides to spread of the spectrum of effects.
Die erfindungsgemässen Mittel können ferner noch Pflanzen-' dünger, Spurenelemente usw. enthalten.The agents according to the invention can furthermore also contain vegetable ' contain fertilizers, trace elements, etc.
Im folgenden werden Aufarbßitungsformen der neuen Harnstoffe .beschrieben. Teile bedeuten Gewichts.te5.le.Forms of preparation of the new ureas are presented below .described. Parts mean weights.te5.le.
Granulatgranules
Zur Herstellung eines 5 %igen Granulates werden die folgenden Stoffe verwendet:The following are used to produce a 5% granulate Substances used:
5 Teile N-[Diäthoxy-phosphinyl-oxy)-N-methyl-N■'-5 parts of N- [diethoxy-phosphinyl-oxy) -N-methyl-N '-
(3,4-dichlorphenyl)-harns toff,
0,25 Teile Epichlorhydrin,
0,25 Teile Cetylpolyglykoläther, 3,50 Teile Polyäthylenglykol ("Carbowax"),
91 Teile Kaolin (Korngrösse 0,3 bis 0,8 mm).(3,4-dichlorophenyl) urea, 0.25 parts epichlorohydrin,
0.25 parts of cetyl polyglycol ether, 3.50 parts of polyethylene glycol ("Carbowax"), 91 parts of kaolin (grain size 0.3 to 0.8 mm).
Die Aktivsubstanz wird mit Epichlorhydrin vermischt und mit 6 Teilen Aceton gelöst, hierauf wird Polyäthylenglykol und Cetylpolyglykoläther zugesetzt. Die so erhaltene Lösung würd auf Kaolin aufgesprüht und anschliessend das Aceton im Vakuum verdampft.The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added added. The solution obtained in this way would be based on kaolin sprayed on and then the acetone evaporated in vacuo.
Zur Herstellung eines a) 50 %igen, b) 25 %igen und c) 10 %igen Spritzpulvers werden folgende Bestandteile verwendet:To produce a) 50%, b) 25% and c) 10% wettable powder, the following ingredients are used:
a) 50 Teile N-lDiäthoxy-phosphinothioyl-oxyJ-N-methyl-a) 50 parts of N-l-diethoxy-phosphinothioyl-oxyJ-N-methyl-
N'-(3,4-dichlor phenyl)-harns toff, 5 Teile Natriumdibutylnaphthylsulfonat, 3 Teile Naphthalinsulfonsäuren-Phenolsulfonsäuren-N '- (3,4-dichlorophenyl) urea, 5 parts of sodium dibutylnaphthylsulphonate, 3 parts of naphthalenesulphonic acids-phenolsulphonic acids-
Formaldehyd-Kondensat (3:2:1), 20 Teile Kaolin,
22 Teile Champagne-Kreide;Formaldehyde condensate (3: 2: 1), 20 parts kaolin,
22 parts of champagne chalk;
Ii) 25 Teile N-lDiäthoxy-phoephinothioyl-oxyl-N-methyl-Ii) 25 parts of N-l-diethoxy-phoephinothioyl-oxyl-N-methyl-
N'- (4-chlor phenyl) -hams toff,N'- (4-chlorophenyl) -ham's toff,
5 Teile Oleylmethyltaurid-Na-Salz,5 parts of oleyl methyl tauride sodium salt,
2,5 Tetle Naphthalineulfonsäure-Formaldehyd-Kondensat,2.5 Tetle of naphthalenesulfonic acid-formaldehyde condensate,
0,5 teile Carboxymethylcellulose,0.5 parts carboxymethyl cellulose,
5 Teile neutrales Kalium-Aluminiumsilikat,5 parts neutral potassium aluminum silicate,
62 Teile Kaolin ;62 parts of kaolin;
009850/2193009850/2193
c) 10 Teile N-rDiäthoxy-phosphinyl-oxyl-N-methyl-N '-c) 10 parts of N-r-diethoxy-phosphinyl-oxyl-N-methyl-N '-
(3,4-dichlorphenyl)-harnstoff, 3 Teile Gemisch der Natriumsalze von gesattigten(3,4-dichlorophenyl) urea, 3 parts mixture of the sodium salts of saturated
Fettalkoholsulfaten,Fatty alcohol sulfates,
5 Teile Naphthalinsulfonsäure-Formaldehyd-Kondensat, 82 Teile Kaolin.5 parts of naphthalenesulfonic acid-formaldehyde condensate, 82 parts of kaolin.
Der angegebene Wirkstoff wird auf die entsprechenden Trägerstoffe (Kaolin und Kreide) aufgezogen und anschliessend vermischt und vermählen. Man erhält Spritzpulver von vorzüglicher Benetzbarkeit und Schwebefähigkeit. Aus solchen Spritzpulvern können durch Verdünnen mit Wasser Suspensionen jeder gewünschten Wirkstoffkon- | zentration erhalten werden. Derartige Suspensionen werden zur Bekämpfung von Unkräutern und Ungräsern in Kulturpflanzungen verwendet» The specified active ingredient is applied to the appropriate carriers (kaolin and chalk) and then mixed and marry. A wettable powder with excellent wettability is obtained and floating ability. Such wettable powders can be diluted with water to produce suspensions of any desired active ingredient concentration centering can be maintained. Such suspensions are used to combat used by weeds and grass weeds in crops »
Zur Herstellung einer 45%igen Paste werden folgende Stoffe verwendet:The following substances are used to produce a 45% paste used:
45 Teile N-lDiäthoxy-phosphinothioyl-oxy]-N-methyl-N'-(3,4-dichlorphenyl)-harnstoff, 45 parts of N-l-diethoxy-phosphinothioyl-oxy] -N-methyl-N '- (3,4-dichlorophenyl) urea,
5 Teile Natriumaluminiumsilikat,5 parts sodium aluminum silicate,
15 Teile Cetylpolyglykoläther, |15 parts of cetyl polyglycol ether, |
2 Teile Spindelöl,2 parts spindle oil,
10 Teile Polyäthylenglykol ("Carbowax"),10 parts of polyethylene glycol ("Carbowax"),
23 Teile Wasser.23 parts of water.
Der Wirkstoff wird mit den Zuschlagstoffen in dazu geeigneten Geräten innig vermischt und vermählen. Man erhält eine Paste, aus der sich durch Verdünnen mit Wasser Suspensionen jeder gewünschten Konzentration herstellen lassen. Diese Suspensionen eignen sich zur Behandlung von Gemüsepflanzungen.The active ingredient is combined with the additives in appropriate Devices intimately mixed and ground. A paste is obtained from which, by diluting with water, suspensions of each are obtained Have the desired concentration produced. These suspensions are suitable for treating vegetable plantings.
009850/2193009850/2193
.Emulsionskonzentrat.Emulsion concentrate
Zur Herstellung eines 10 %igen Emulsionskonzentrates werdenFor the production of a 10% emulsion concentrate will
10 Teile N-fDiä'thoxy-phosphinothioyl-oxyi-N-methyl-N1-10 parts of N-fDiethoxy-phosphinothioyl-oxyi-N-methyl-N 1 -
(3,4~dichlorphenyl)-harnstoff,(3,4 ~ dichlorophenyl) urea,
15 Teile Oleylpolyglykoläther mit 8 Mol Aethylenoxyd, 75 Teile Isophoron15 parts of oleyl polyglycol ether with 8 moles of ethylene oxide, 75 parts of isophorone
miteinander vermischt. Dieses Konzentrat kann mit Wasser zu Emulsionen auf geeignete Konzentratione\i verdünnt werden. Solche Emulsionen eignen sich zur Bekämpfung von Unkräutarn in Kulturpflanzen, wie z.B. Baumwolle, Mais, etc.mixed together. This concentrate can be mixed with water to form emulsions be diluted to suitable concentrations. Such emulsions are suitable for controlling weeds in cultivated plants, such as cotton, corn, etc.
QQf85Q/2193QQf85Q / 2193
Claims (5)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH864469A CH509352A (en) | 1969-06-06 | 1969-06-06 | Process for the production of new ureas and their use for combating weeds and grass weeds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2027772A1 true DE2027772A1 (en) | 1970-12-10 |
Family
ID=4343011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702027772 Pending DE2027772A1 (en) | 1969-06-06 | 1970-06-05 | New ureas and their use to control weeds and grass weeds |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4820300B1 (en) |
| AU (1) | AU1600970A (en) |
| BR (1) | BR7019542D0 (en) |
| CH (1) | CH509352A (en) |
| DE (1) | DE2027772A1 (en) |
| ES (3) | ES380457A1 (en) |
| FR (1) | FR2049981A5 (en) |
| GB (1) | GB1298730A (en) |
-
1969
- 1969-06-06 CH CH864469A patent/CH509352A/en not_active IP Right Cessation
-
1970
- 1970-06-05 BR BR21954270A patent/BR7019542D0/en unknown
- 1970-06-05 ES ES380457A patent/ES380457A1/en not_active Expired
- 1970-06-05 FR FR7020733A patent/FR2049981A5/fr not_active Expired
- 1970-06-05 JP JP4837370A patent/JPS4820300B1/ja active Pending
- 1970-06-05 DE DE19702027772 patent/DE2027772A1/en active Pending
- 1970-06-05 ES ES380458A patent/ES380458A1/en not_active Expired
- 1970-06-05 GB GB2713970A patent/GB1298730A/en not_active Expired
- 1970-06-05 ES ES380456A patent/ES380456A1/en not_active Expired
- 1970-06-05 AU AU16009/70A patent/AU1600970A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1298730A (en) | 1972-12-06 |
| ES380457A1 (en) | 1972-10-01 |
| ES380458A1 (en) | 1972-10-01 |
| ES380456A1 (en) | 1972-09-01 |
| FR2049981A5 (en) | 1971-03-26 |
| AU1600970A (en) | 1971-12-09 |
| CH509352A (en) | 1971-06-30 |
| BR7019542D0 (en) | 1973-04-17 |
| JPS4820300B1 (en) | 1973-06-20 |
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| Date | Code | Title | Description |
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| OHW | Rejection |