DE2948095A1 - N-phenoxy-alkanoyl amino acid derivs. - useful as herbicides, fungicides and biocides - Google Patents
N-phenoxy-alkanoyl amino acid derivs. - useful as herbicides, fungicides and biocidesInfo
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- DE2948095A1 DE2948095A1 DE19792948095 DE2948095A DE2948095A1 DE 2948095 A1 DE2948095 A1 DE 2948095A1 DE 19792948095 DE19792948095 DE 19792948095 DE 2948095 A DE2948095 A DE 2948095A DE 2948095 A1 DE2948095 A1 DE 2948095A1
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
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Abstract
Description
Phenoxialkan- und Phenoxialkencarbonsäuren und deren Derivate,Phenoxialcanic and phenoxialkenecarboxylic acids and their derivatives,
ihre Herstellung und Verwendung Aminosäurekonjugate von Phenoxicarboneursn der Formel in der A für Wasserstoff und/oder einen Halogenrest und R1 für Wasserstoff oder gegebenenfalls einen Methylrest steht und E die Bedeutung einer Methylengruppe hat, welche durch einen Methyl-, Hydroximethyl-, Isopropyl-, Mercaptomethyl-, Phenyl-, 4-Hydroxiphenyl-, Hydroxiethyl- bzw. Carboxiethylrest substituiert sein kann, sind in der Literatur als Mittel mit herbiziden Eigenschatten beschrieben worden [Feung, Hemilton und Mumma, 3. Agric.Their preparation and use Amino acid conjugates of Phenoxicarboneursn of the formula in which A stands for hydrogen and / or a halogen radical and R1 for hydrogen or optionally a methyl radical and E has the meaning of a methylene group which is replaced by a methyl, hydroxymethyl, isopropyl, mercaptomethyl, phenyl, 4-hydroxyphenyl, Hydroxiethyl or Carboxiethylrest can be substituted, have been described in the literature as agents with herbicidal properties [Feung, Hemilton and Mumma, 3rd Agric.
Food Chem., Vol. 25, No. 4 (1977), S 898).Food Chem., Vol. 25, No. 4 (1977), p 898).
Es zeigte sich, daß Verbindungen, in denen A durch einen Rest der Formeln oder oder in denen X für -0- oder -CH2- oder -OCH2- steht und R1 eine CH3-Gruppe ist, eine breiteherbizido Wirkung aufweisen und gute Verträglichkeiten gegenüber Nutzpflanzen zeigen. Sie sind des weiteren auch als Fungizide verwendbar.It was found that compounds in which A is replaced by a remainder of the formulas or or in which X stands for -0- or -CH2- or -OCH2- and R1 is a CH3 group, have a broad herbicidal action and are well tolerated by useful plants. They can also be used as fungicides.
Gegenstand der Erfindung sind daher Verbindungen der allgemeinen Formel (I), in welcher A für einen Rest der Formeln oder oder steht und hierin R die Bedeutung eines Halogen-, Trifluermethyl-, Cyano-, Nitro-, Halogenmethoxi- oder Methylrestes hat und n für eine ganze Zahl von 0 bis 3 steht und O die Bedeutung von =CH- bzw. von =N- hat und Y für -O-, -S- oder -NCH3 steht, X die Bedeutung von -0-, -OCH2-, -CH2- hat und 2 für Wasserstoff, einen Halogenrest, einen Trifluormethylrest oder einen Methylrest steht, R1 die Bedeutung einer Nethyl- oder Methoximethylgruppe hat und B für eine direkte Bindung steht, aber auch -CH2CH2-oder -CH=CH- sein kann und R³ die Bedeutung von Wasserstoff bzw. einer 1,3-Propylengruppe hat, welche mit E verknüpft ist, wobei in diesem 3 Felle E für =CH- steht, bei R3 = Wasserstoff E Jedoch eine Alkylenkette mit 1 bis 3 C-Atomen, die gegebenenfalls durch einen Phenyl-, Benzyl-, Methylthio-, Amlnocarbonyl- oder Guanidylrest und/oder ein oder zweifach durch eine Alkylgruppe mit 1 bis 4 C-Atomen substituiert sein kann, bedeutet und G für eine -CN-Gruppe oder eine -COOR4-Gruppe, in der R4 die Bedeutung von Wasserstoff oder einer Alkylgruppe mit 1 bis 4 C-Atomen hat, steht, cit der Maßgabe, daß, falls A einen Rest darstellt und X für -0- oder -CH2- steht und R1 Methyl und 6 die direkte Bindung bedeuten sowie R für Wasserstoff steht, die Gruppierung E-G nicht die Bedeutung einer Gruppe der Formel -CH2CH2CN, -CH2COOR4, oder hat, wobei R4 für Alkyl mit 1 bis 4 C-Atomen steht.The invention therefore relates to compounds of the general formula (I), in which A stands for a remainder of the formulas or or and here R has the meaning of a halogen, trifluoromethyl, cyano, nitro, halomethoxy or methyl radical and n is an integer from 0 to 3 and O has the meaning of = CH- or = N- and Y is -O-, -S- or -NCH3, X is -0-, -OCH2-, -CH2- and 2 is hydrogen, a halogen radical, a trifluoromethyl radical or a methyl radical, R1 is a Has a methyl or methoxymethyl group and B stands for a direct bond, but can also be -CH2CH2- or -CH = CH- and R³ has the meaning of hydrogen or a 1,3-propylene group which is linked to E, where in These 3 skins E stands for = CH-, with R3 = hydrogen E, however, an alkylene chain with 1 to 3 carbon atoms, which is optionally through a phenyl, benzyl, methylthio, aminocarbonyl or guanidyl radical and / or one or two times through an alkyl group with 1 to 4 carbon atoms can be substituted, and G for a -CN group or a -COOR4 group in which R4 is the The meaning of hydrogen or an alkyl group having 1 to 4 carbon atoms is, cit with the proviso that, if A is a radical represents and X represents -0- or -CH2- and R1 represents methyl and 6 represents the direct bond and R represents hydrogen, the grouping EG does not represent a group of the formula -CH2CH2CN, -CH2COOR4, or has, where R4 stands for alkyl having 1 to 4 carbon atoms.
Von den neuen Verbindungen der Formel (I) sind solche Verbindungen der allgemeinen Formel (III) uorin für einen Rest oder oder steht und worin die Bedeutung eines Trifluormethyl-, Brom- oder Chlorrestes, die Bedeutung eines Chlor- oder Nitrorestes hat, wobei der Chlorrest besonders bevorzugt ist, n für 0 oder 1 und Hal für einen Chlor- oder Bromrest steht und Y die Bedeutung von -0- oder -S- hat und R³ Wasserstoff bedeutet sowie E-G für Reste der Formeln -CH2COOH, -CH2CH2COOR4, -CH2CH2CH2COOR4 und hierin R4 für Wasserstoff, Methyl oder Ethyl steht, bevorzugt.Of the new compounds of the formula (I), those compounds of the general formula (III) are uorin for a rest or or and in which the meaning of a trifluoromethyl, bromine or chlorine radical has the meaning of a chlorine or nitro radical, the chlorine radical being particularly preferred, n stands for 0 or 1 and Hal stands for a chlorine or bromine radical and Y stands for - 0- or -S- and R³ is hydrogen and EG for radicals of the formulas -CH2COOH, -CH2CH2COOR4, -CH2CH2CH2COOR4 and R4 herein represents hydrogen, methyl or ethyl, is preferred.
Die beanspruchten Verbindungen der allgemeinen Formel (I) besitzen ein Asymmetriezentrum am C-Atom der Alkan-(en)-carbonsiure und liegen üblicherweise als Racemats vor. Es ist möglich, diese nach üblichen Methoden, z. B. durch Kristallisation zu trennen bzw. die optischen Antipoden durch gezielte Synthesen unter Einsatz von optisch-aktivem Ausgangsmaterial herzustellen (DE-OS 27 58 002). Daneben können die Verbindungen ein weiteres Asymmetriezentrum im Aminosäureteil aufweisen. Durch Einsatz von optisch aktiven Ausgangsmaterialien erhält man such hier optisch aktive Endprodukte.The claimed compounds of general formula (I) have a center of asymmetry on the carbon atom of the alkane (en) carboxylic acid and are usually as racemats. It is possible to do this by conventional methods, e.g. B. by crystallization to separate or the optical antipodes by targeted syntheses using produce optically active starting material (DE-OS 27 58 002). Besides that, you can the compounds have a further center of asymmetry in the amino acid part. By The use of optically active starting materials results in optically active ones End products.
Die Herstellung der Verbindungen der allgemeinen Formel (1) mit G w -COOH erfolgt in der Weise, daß man Säurechloride der Formel (II) in der A, X, R1, R2 und B die oben angegebene Bedeutung haben, mit Aminosäuren der Formel in der R3 und E die bereits angegebene Bedeutung haben, umsetzt.The compounds of the general formula (1) with G w -COOH are prepared in such a way that acid chlorides of the formula (II) in which A, X, R1, R2 and B have the meaning given above, with amino acids of the formula in which R3 and E have the meaning already given.
Man verwendet hierbei pro Mol Säurechlorid 1 bis 1,2 Mol Aminosäure und arbeitet im Zweiphasensystem Wasser/organisches Lösungsmittel und in Gegenwart von Alkali bei 0 bis 20 T. Das erhaltene Reaktionsgemisch wird sodann mit einer Mineralsäure bis zur Kongoreaktion angesäuert und in bekannter Weise aufgearbeitet.1 to 1.2 moles of amino acid are used per mole of acid chloride and works in the two-phase system water / organic solvent and in the presence of alkali at 0 to 20 T. The reaction mixture obtained is then with a Mineral acid acidified to the Congo reaction and worked up in a known manner.
Will man solche Verbindungen der Formel (I), in denen G = -CN ist, herstellen, eo werden die Säurechloride der Formel (II) mit obiger Bedeutung mit Chlorhydraten von Aminosäurenitrilen in denen R Wasserstoff ist und E die oben angegebene Bedeutung hat, zur Umsetzung gebracht, wobei äquimolare mengen bzw. Verbindung (II) mit bis zu 10 % Überschuß in einem inerten Solvens und in Gegenwart der doppelt bis dreifach äquimolaren Menge einer tertiären Base eingesetzt werden und man bei Temperaturen von 20 bis 100, vorzugsweise 40 bis 70 s arbeitet.If one wishes to prepare compounds of the formula (I) in which G = -CN, the acid chlorides of the formula (II) with the above meaning are combined with chlorohydrates of amino acid nitriles in which R is hydrogen and E has the meaning given above, brought to reaction, using equimolar amounts or compound (II) with up to 10% excess in an inert solvent and in the presence of twice to three times the equimolar amount of a tertiary base and one works at temperatures of 20 to 100, preferably 40 to 70 seconds.
Zur Herstellung solcher Verbindungen mit der Formel (I), bei denen G = COOR4 ist und R4 hierein die Bedeutung einer Alkylgruppe mit 1 bis 4 C-Atomen hat, und A, X, R1, B, R³ und E die oben angegebene Bedeutung haben, mit der Maßgabe, daß, falls der Rest A bedeutet und X für -O- bzw. für -CH2- steht und R1 Methyl, B die direkte Bindung und R3 Wasserstoff bedeuten, die Gruppierung E-G nicht für einen Rest der Formel oder -CH2C00R4 mit.R4 für C1- bis C4-Alkyl stehen 8011, setzt man Säurechlorids der Formel (II) mit Aminosäureestern der Formel in der R3, E und G die oben angegebene Bedeutung mit der für E-G einschränkenden Maß gebe haben kann, um. man arbeitet in einem inerten Lösungsmittel bei Temperaturen von 0 bis 40, bevorzugt 0 bis 20 °C und veruendet im allgemeinen äquimolare Mengen Säurechlorid und Aminosäureester in Anwesenheit eines säurebindenden Mittels. Letzteres ist überflüssig, wenn man pro Mol Säurechlorid 2 Mol Aminosäureester einsetzt.For the preparation of those compounds of the formula (I) in which G = COOR4 and R4 here has the meaning of an alkyl group with 1 to 4 carbon atoms, and A, X, R1, B, R³ and E have the meaning given above , with the proviso that if the remainder A and X is -O- or -CH2- and R1 is methyl, B is the direct bond and R3 is hydrogen, the group EG is not a radical of the formula or -CH2C00R4 mit.R4 for C1- to C4-alkyl 8011, acid chloride of the formula (II) is used with amino acid esters of the formula in which R3, E and G can have the meaning given above with the restrictive measure for EG. the reaction is carried out in an inert solvent at from 0 to 40 ° C., preferably from 0 to 20 ° C., and generally equimolar amounts of acid chloride and amino acid ester are used in the presence of an acid-binding agent. The latter is superfluous if 2 moles of amino acid ester are used per mole of acid chloride.
Unter wäßrigem Alkali versteht man Lösungen von NaOH oder KOH in Wasser, wobei 0,1 bis 2-normale Lösungen, bevorzugt 1-n-Lösungen, zum Einsatz kommen.Aqueous alkali means solutions of NaOH or KOH in water, 0.1 to 2 normal solutions, preferably 1-n solutions, are used.
Minerelsäuren sind bevorzugt HC1 oder H2S04, die mit Wasser verdünnt im Verhältnis 1:2 bis 1s1, bevorzugt 1:1, angewandt werden.Mineral acids are preferred HC1 or H2S04, which are diluted with water in a ratio of 1: 2 to 1s1, preferably 1: 1, can be used.
Unter inerten Lösungsmitteln worden z. 8. Toluol, Xylol, Diethylether, Tetrahydrofuran oder Dioxan, sber auch halogenierte Kohlanwasserstoffe wie CH2Cl2, CHCl3, CCl4 verstanden. Bevorzugt wird Toluol verwendet.Inert solvents have been used, for. 8. Toluene, xylene, diethyl ether, Tetrahydrofuran or dioxane, but also halogenated hydrocarbons such as CH2Cl2, CHCl3, CCl4 understood. Toluene is preferably used.
Geeignete tertiäre Basen sind beispielsweise Triethylamin und Pyridin. Unter säurebindenden Mitteln werden ebenfalls tertiäre organische Basen, aber auch anorganisch. Basen wie NaOH, KOH usw. verstanden.Suitable tertiary bases are, for example, triethylamine and pyridine. Acid-binding agents also include tertiary organic bases, as well inorganic. Bases such as NaOH, KOH, etc. understood.
Die Herstellung der Ausgengesäurechloride der Formel (II) erfolgt aus den jeweiligen substituierten Phanoxipropionsäuren (DE-OSS 22 23 894, 24 33 067, 26 01 548, 26 40 730, 24 17 487, 25 46 251) beispielsweise durch Umsetzen mit Thionylchlorid in an sich bekannter Weise, z. B. nach der Vorschrift im wOrganikum", VEB-Verlag der Wissenschaften.The Ausgengesäurechloride of the formula (II) is produced from the respective substituted phanoxypropionic acids (DE-OSS 22 23 894, 24 33 067, 26 01 548, 26 40 730, 24 17 487, 25 46 251) for example by moving with Thionyl chloride in a manner known per se, e.g. B. according to the regulation in the wOrganikum ", VEB publishing house of the sciences.
Typische Säuren sind z. 8. 2-[4'-(2",4"-Dichlorbenzyl)-phenoxi]-propionsäure, 2-[4'-(3",5"-Dichlorpyridyl-2"-oxi)-phenoxi]-propionsäure, 2-[4'-(6"-Chlorbenzthiazolyl-2"-oxi)-phenoxi]-propionsäure, 2-[4'-(6"-Brombenzthiazolyl-2"-oxi)-phenoxi]-propionsäure, 2-[4'-(5"-Chlorpyrimdyl-2"-oxi)-phenoxi]-propion säure, 2-[4'-(6"-Chlorbenzoxazolyl-2"-oxi)-phenoxi]-propionsäure, 2-[4'-(6"-Chlorbenzoxazoly-2"-methylen)-phenoxi]-propionsäure, 2-[4'-(6"-Chlorbenzthiazolyl-2"-methylen)-phenoxi]-propionsäure, 2-[4'-(2",4"-Dichlorphenoxi)-phenoxi]-propionsäure, 4-[4'-(2",4"-Dichlorphenoxi)-phenoxi]-valeriansäure, 2-[4'-(4"-Chlorphenoxi)-phenoxi]-propionsäure, 2-[4'-(4"-Chlorphenoximethylen)-phenoxi]-propionsäure, 4-[4'-(4"-Trifluoromethylphenoxi)-phenoxi]-penten-2-carbonsäure, 2-[4'-(4"-Trifluoromethylphenoxi)-phenoxi]-propion säure, 2-[4'-(5"-Chlorbenzoxazolyl-2n-oxi)-phenoxi-propionsäure, 4-[4'-(6"-Chlorbenzoxazolyl-2"-oxi)-phenoxi]-valeriansäure, 4-[4'-(4"-Trifluoromethylphenoxi)-phenoxi]-valeriansäure, 2-[4'-(2"-Chlor-4"-bromphenoxi)-phenoxi]-propionsäure.Typical acids are e.g. 8. 2- [4 '- (2 ", 4" -Dichlorobenzyl) -phenoxy] -propionic acid, 2- [4 '- (3 ", 5" -Dichlorpyridyl-2 "-oxy) -phenoxy] propionic acid, 2- [4' - (6" -chlorobenzothiazolyl-2 "-oxy) -phenoxy] propionic acid, 2- [4 '- (6 "-Bromobenzothiazolyl-2" -oxy) -phenoxy] -propionic acid, 2- [4' - (5 "-chloropyrimdyl-2" -oxy) -phenoxy] -propion acid, 2- [4 '- (6 "-chlorobenzoxazolyl-2" -oxy) -phenoxy] -propionic acid, 2- [4' - (6 "-chlorobenzoxazoly-2" -methylene) -phenoxy] -propionic acid, 2- [4 '- (6 "-chlorobenzothiazolyl-2" -methylene) -phenoxy] propionic acid, 2- [4' - (2 ", 4" -dichlorophenoxy) -phenoxy] propionic acid, 4- [4 '- (2 ", 4" -Dichlorphenoxi) -phenoxi] -valeric acid, 2- [4' - (4 "-chlorophenoxi) -phenoxi] -propionic acid, 2- [4 '- (4 "-Chlorophenoximethylene) -phenoxy] -propionic acid, 4- [4' - (4" -Trifluoromethylphenoxi) -phenoxy] -pentene-2-carboxylic acid, 2- [4 '- (4 "-Trifluoromethylphenoxi) -phenoxi] -propionic acid, 2- [4' - (5" -chlorobenzoxazolyl-2n-oxi) -phenoxi-propionic acid, 4- [4 '- (6 "-chlorobenzoxazolyl-2" -oxy) -phenoxy] -valeric acid, 4- [4' - (4 "-trifluoromethylphenoxy) -phenoxy] -valeric acid, 2- [4 '- (2 "-chloro-4" -bromophenoxy) phenoxy] propionic acid.
Typische Aminosäuren sind z. 8.: Glycin, L-Alanin, DL-Alanin, DL-Phenylglycin, L-Isoleucin, DL-Isoleucin, OL-Valin, L-Methionin, DL-Leucin, 4-Aminobuttersäure, 3-Aminobuttersäure, DL-Aspargin, 2-Aminopropionsäure, Guanidin, L-Prolin usw.Typical amino acids are e.g. 8 .: Glycine, L-Alanine, DL-Alanine, DL-Phenylglycine, L-isoleucine, DL-isoleucine, OL-valine, L-methionine, DL-leucine, 4-aminobutyric acid, 3-aminobutyric acid, DL-asparagine, 2-aminopropionic acid, guanidine, L-proline, etc.
Ester und AminoeSurenitrile (mit G = COOR4 und CN) sind in Form der Hydrochloride, aus denen sie durch Neutralsetion erhalten werden tE. Fischer, Ber. Dtsch. Chem. Ges. 34, 433 (1901)],zum Teil im Handel erhältlich.Esters and AminoeSurenitrile (with G = COOR4 and CN) are in the form of the Hydrochlorides, from which they are obtained by neutral deletion tE. Fischer, Ber. German Chem. Ges. 34, 433 (1901)], some of which are commercially available.
Typische Aminosäureester und -nitrile sind z.B.: DL-Aminophenylacetonitril, DL-Aminoacetonitril, Glycinmethylester, Glycinathylester, 3-Aminobuttersäuremethylester, 2-Aminopropionsäureetghylester, L-Tyrosinethylester, 4-Aminobuttersäureethylester, L-Leucinmethylester u.e.Typical amino acid esters and nitriles are e.g .: DL-aminophenylacetonitrile, DL-aminoacetonitrile, glycine methyl ester, glycine ethyl ester, 3-aminobutyric acid methyl ester, Ethyl 2-aminopropionate, L-tyrosine ethyl ester, ethyl 4-aminobutyrate, L-leucine methyl ester u.e.
Bei der Synthese der neuen Verbindungen wird, wenn zan mit einer Aminosäure umsetzt, z.B. in der Water vorgegangen, daß man die Aminosäure in Alkaii löst, diene Lösung auf ca. 5 °C abkühlt und dann langsam unter Rühren eine Lösung des Slurechloride in einem Inertlösungsmittel, wie z.B. Toluol, zutropf. Man rührt etwa zwei Stunden bei Raumtemperatur, extrahiert dann lit Ether oder Toluol und säuert die abgetrennte, wäßrige Phase mit Salzsäure bis zur Kongoresktion en. Durch Extraktion erhält man nach dem Abdempfen des Lösungsmittels die gewünschten Verbindungen als Öle oder Feststeffe.In the synthesis of the new compounds is used when zan with an amino acid converts, e.g. proceeded in the water that one dissolves the amino acid in alkali, serve Solution cools to approx. 5 ° C and then slowly a solution of the slurechloride with stirring in an inert solvent such as toluene, added dropwise. The mixture is stirred for about two hours at room temperature, then extracted lit ether or toluene and acidified the separated, aqueous phase with hydrochloric acid up to congestion. Extraction gives after removing the solvent the desired compounds as oils or Firmness.
Sollen Aminosäureesternitrile umgesetzt werden, eo geht nan von den Hydrochloriden aus, setzt aus diesen die A.inoverbindungen frei und läßt mit einer Lösung des Säurechloride in Toluol reagieren, wobei die freiwerdende HCl entweder durch einen Überschuß der Aminmoverbindung oder mittele einer tertiären Base neutralisiert wird. Man rührt dennn zwei Stunden nach, extrahiart die Hydrochloride mit Wasser und dempft die Toluolphase nach dem Trocknen im Vakuum ab. Es verbleiben auch hier feststoffe oder Öle.If amino acid ester nitriles are to be converted, nan goes from the Hydrochlorides from, releases the amino compounds from these and leaves with a Solution of the acid chlorides in toluene react, with either the HCl being released neutralized by an excess of the aminocompound or by means of a tertiary base will. The mixture is then stirred for two hours and the hydrochloride is extra hard with water and evaporates the toluene phase after drying in vacuo. It also remains here solids or oils.
Mit den erfindungsgemäßen Substanzen läßt sich ein breitem Spektrum wirtschaftlich uithtigor annueller und auedauernder Ungräser sowohl im Vor- als auch im Nachauflaufverfahren bekämpfen.The substances according to the invention can be used in a wide range economically uithtigor annual and perennial grass weeds both in the fore and also fight in the post-emergence method.
Dem als Vergleichsaittel herangezogenen strukturverwandten Phenoxipropinyl-DL-alanin sind sie weit Oberlegen, inbesondere bei der Bekämpfung perennierender Ungräser@eie Quecke und Beriudegras in Vorauflauf und bei der Nachauflaufwirkung auf annuelle Schadgräser. Da die neuen Verbindungen für viele monokotyle und dikotyle Kulturpflanzen in den harbizid wirknamen Dosierungen völlig unschädlich sind, können sie somit auch zur Bekämpfung grasartiger Unkräuter in dissen Kulturen eingesetzt werden.The structurally related phenoxipropinyl-DL-alanine used as a comparative agent they are far superior, especially in the control of perennial weeds Couch grass and beriudegrass in pre-emergence and in the post-emergence effect on annuelle Grass weeds. As the new compounds for many monocotyledon and dicotyledon crops in the harbicidal active name dosages are completely harmless, they can therefore also be used to control grass-like weeds in these crops will.
Die Verbindungen sind des weiteren als Fungizide brauchbar. So zeJnen sie gegenphytopathogene Pilze eine gute Wirkung, insbesondere gegen Botrytis cinerea,Piricularia oryzae und Pythium ultimum. Auch im technischen Biozid-Bereich wird eine gute fungizide, bakterizide und algizide Wirkung, insbesondere gegen Holz-zerstörende Basidiomyceten und Bacillus subtilis, erreicht.The compounds can also be used as fungicides. So draw they have a good effect against phytopathogenic fungi, in particular against Botrytis cinerea, Piricularia oryzae and Pythium ultimum. A good fungicidal, bactericidal and algicidal action, especially against wood-destroying Basidiomycetes and Bacillus subtilis.
Folgende Beispiele dienen der weiteren Erläuterung der Erfindung.The following examples serve to further illustrate the invention.
Die Beispiele 1 bis 3 sind gleichzeitig Muster für drei Verfahrensmethoden (Methode A, Methode B und Methode C), auf welche in der die Beispiele 4 bis 46 enthaltenen Tabelle 2 verwiesen wird. Die biologischen Beispiele zeigen die Verwendbarkeit der neuen Verbindungen als Herbizide und Fungizide.Examples 1 to 3 are simultaneously samples for three process methods (Method A, Method B and Method C), on which the Examples 4 to 46 contained Table 2 is referenced. The biological examples show the usefulness of the new compounds as herbicides and fungicides.
Beispiel 1 (Arbeitsweise nach Methode A) 2-[4'-(2",4"-Dichlorphenoxi)-phenoxi]-propionyl-DL-alanin 8,9 g (0,1 Mol) DL-Alanin und 300 ml 1-n-NsOH (0,3 Mol) werden bei etwa 5 S vorgelegt und unter Eiskühlung mit einer Lösung von 36,1 g (0,1 Mol) 2-[4'-(2",4"-Dichlorphenoxi)-phenoxi]-propionylchlorid in 30 ml Toluol langsam versetzt, wobei die Temperatur 15 α nicht überschreiten soll. Man rührt zwei Stunden bei Raumtemperatur weiter, extrahiert dann mit Ether und säuert die wäßrige Phase mit HC1 (1:1) bis zur Kongoreaktion an. Dann wird die saure Lösung mit Ether mehrfach extrahiert. Die vereinigten Etherextrakte trocknet man mit Nu 2504 und entfernt das Lösungsmittel im Vakuum. Es verbleiben 30,4 g Produkt vom Schm. 55 T.Example 1 (procedure according to method A) 2- [4 '- (2 ", 4" -Dichlorophenoxy) -phenoxy] -propionyl-DL-alanine 8.9 g (0.1 mol) of DL-alanine and 300 ml of 1-n-NsOH (0.3 mol) are initially introduced at about 5 ° C and with ice-cooling with a solution of 36.1 g (0.1 mol) of 2- [4 '- (2 ", 4" -Dichlorophenoxy) -phenoxy] -propionyl chloride slowly added in 30 ml of toluene, the temperature not exceeding 15 α target. The mixture is stirred for a further two hours at room temperature, then extracted with ether and acidify the aqueous phase with HC1 (1: 1) until the Congo reaction. Then the acidic solution extracted several times with ether. The combined ether extracts dry one with Nu 2504 and the solvent is removed in vacuo. There remain 30.4 g of product from Schm. 55 T.
Beispiel 2 (Arbeitsweise nach Methode 8) 2-[4'-(3",5"-Diclorpyridyl-2"-oxi)-phenoxi]-propionyl-ßalaninethylester 23 g (0,2 Plol) ß-Alaninethylester (hergestellt aus ß-Alaninethylesterchlorhydrat) in 100 ml Toluol werden bei etwa 5 α mit einer Lösung von 0,1 Mol 2-[4'-(3",5"-Dichlorpyridyl-2")-phenoxi]-propionylchlorid in 30 ml Toluol so versetzt, daß die Temperatur 15 α nicht überschreitet. Man rührt einige Zeit bei Raumtemperatur nach und trennt dann entweder durch Absaugen vom ausgefallenen Alaninesterchlorhydrat ab und rotiert die mutterlauge im Vakuum ein, oder aber, man schüttelt mit Wasser aus, trennt die organische Phase ab, trocknet mit Na2SO4 und rotiert die organische Phase im Vakuum ab. Es hinterbleiben je 32,4 g Feststoff vom Schmp. 87 Cc.Example 2 (procedure according to method 8) 2- [4 '- (3 ", 5" -Diclorpyridyl-2 "-oxi) -phenoxy] -propionyl-salanine ethyl ester 23 g (0.2 plol) ß-alanine ethyl ester (made from ß-alanine ethyl ester chlorohydrate) in 100 ml of toluene are at about 5 α with a solution of 0.1 mol of 2- [4 '- (3 ", 5" -Dichlorpyridyl-2 ") - phenoxy] propionyl chloride added in 30 ml of toluene so that the temperature does not exceed 15 α. The mixture is stirred for some time at room temperature and then either separated by suction from the precipitated alanine ester chlorohydrate and rotates the mother liquor in a vacuum or alternatively, one shakes out with water, separates the organic phase and dries with Na2SO4 and the organic phase rotates off in vacuo. There remain 32.4 each g of solid with a melting point of 87 cc.
Beispiel 3 (Arbeitsweise nach Methode C) 2-[4'-(2"-Chlor-4"-bromphenoxi)-phenoxi]-propionylaminoacetonitril 0,1 Mol 2-[4'-(2"-Chlor-4"-bromphenoxi)-phenoxi]-propionsäurechlorid in 30 ml Toluol werden zu 10,2 g (0,11 Mol) Aminoacetonitrilhydrochlorid in 70 ml Toluol gegeben. Dann fügt man 20,4 g (0,2 Mol) Triethylamin zu, hält 2 1/2 Stunden bei 50 Cc, kühlt auf 20 Cc, filtriert vom Ungelösten ab und verdampft das Lösungsmittel im Vakuum. Der verbliebene Pückstand wird aus CCl4 umkristallisiert. Ausbeute 7,9 g der gewünschten Verbindung.Example 3 (procedure according to method C) 2- [4 '- (2 "-chloro-4" -bromophenoxy) phenoxy] propionylaminoacetonitrile 0.1 mol of 2- [4 '- (2 "-chloro-4" -bromophenoxy) phenoxy] propionic acid chloride in 30 ml of toluene are added to 10.2 g (0.11 mol) of aminoacetonitrile hydrochloride in 70 ml of toluene. Then 20.4 g (0.2 mol) of triethylamine are added, the mixture is kept at 50 ° C. for 2 1/2 hours, and the mixture is cooled to 20 Cc, filtered off from the undissolved and the solvent evaporated in vacuo. The remaining residue is recrystallized from CCl4. Yield 7.9 g of the desired Link.
Schmp. 116 Cc.M.p. 116 cc.
Beispiele 4 bis 46 Es wurde nach den in den Beispielen 1 bis 3 angegebenen Methoden mit den dortigen Molmengen unter Einsatz der in der nachstehenden Tabelle 1 aufgeführten Ausgangematerialian gearbeitet. In der Tabelle 2 ist die Struktur der Verfahrensprodukte und der Schmelz- punkt derselben, die Ausbeute sowie die angewandte Methode dargelegt.Examples 4 to 46 The procedures given in Examples 1 to 3 were followed Methods with the molar amounts there using the table below 1 listed starting materialian worked. In Table 2 is the structure the process products and the melting point of the same, the yield as well as the method used.
Tabelle 1
Ber. C 59,7 H 4,7 N 3,3 Gef. C 59,6 H 4,7 N 3,2 beispiele 48 bis 59 Analog Beispiele 2 und 47 wurden folgende Verbindungen hergestellt. Ber. C 59.7 H 4.7 N 3.3 Found C 59.6 H 4.7 N 3.2 Examples 48 to 59 The following compounds were prepared analogously to Examples 2 and 47.
Tabelle 3
Samen bzw. Rhizome verschiedener annueller und perennierendor Ungräser wurden in Töpfe ausgesät und die als benetzbare Pulver oder Emulsionskonzentrat formulierten erfindungsgemäßen Mittel auf die Erdoberfläche gesprüht. Als Vergleichssubstanz diente Phenoxipropionyl-DL-alanin Nach vier Wochen Standzeit im (;ewächshaus wurde die prozentualo Schädigung der Versuchslanzen im Vergleich zu Unbehandelt visuell bonitiert.Seeds or rhizomes of various annual and perennial weed grasses were sown in pots and used as a wettable powder or emulsion concentrate formulated agents according to the invention sprayed onto the surface of the earth. As a reference substance served phenoxipropionyl-DL-alanine After four weeks standing in the (; greenhouse was the percentage damage to the test lances compared to untreated visual rated.
Dabei ergaben sich die in nachstehender Tabelle 4 dargestellten Versuchsergebnisse, welche klar belegen, daß die erfindungsgemäßen Verbindungen gegen viele wirtschaftlich wichtige annuelle Ungräser eine hervorragende herbizide Wirkung aufweisen.The test results shown in Table 4 below were obtained, which clearly show that the compounds according to the invention are against many economical important annual weed grasses have an excellent herbicidal effect.
Die in der Tabelle verwendeten Abkürzungen bedeuten: AVF = Avena ALM = Alopecurus SAL = Setaria POA = Poa LOM = Lolium ECG = Echinochloa Die Dosierung ist als kg Aktivsubstanz pro Hektar angegeben.The abbreviations used in the table mean: AVF = Avena ALM = Alopecurus SAL = Setaria POA = Poa LOM = Lolium ECG = Echinochloa The dosage is given as kg of active substance per hectare.
Tabelle 4
Tabelle 5
Samen bzw. Rhizoms verschiedener einjähriger und mehrjähriger Schadgräser wurden in Töpfe ausgesät und im Gewächshaus angezogen.Seeds or rhizomes of various annual and perennial weed grasses were sown in pots and grown in the greenhouse.
Drei Wochen nach der Aussaat wurden die als Spritzpulver oder Emulsionskonzentrat formulierten Verbindungen auf die Pflanzen gesprüht. Nach vierwöchiger Standzeit im Gewächshaus wurde die prozentuale Schädigung der Versuchspflanzen im Vergleich zu Unbehandelt optisch bonitiert.Three weeks after sowing, they were available as a wettable powder or emulsion concentrate formulated compounds sprayed on the plants. After four weeks of standing in the greenhouse the percentage damage to the test plants was compared optically rated too untreated.
Es zeigte sich, daß die neuen Verbindungen gegen ein breites Spektrum von Ungräsern hervorragend herbizid wirksam sind. Einige wiesen auch bei mehrjährigen Schadgräsern eine beachtliche herbizide Wirkung auf (Tabelle 6).It was found that the new compounds against a broad spectrum of grass weeds have excellent herbicidal properties. Some also pointed at perennials Weeds have a remarkable herbicidal effect (Table 6).
Tabelle 6
Tabelle 7
Tabelle 8
Tabelle 9
Tabelle 10
Dem Agar waren zuvor im flüssigan Zustand die beanspruchten Verbindungen in den in Tabelle 11 angegebenen Konzentrationen zugesetzt worden. Sechs Tage nach der Beimpfung der Platten wurde der Durchmesser der Pilzkolonisn auf dem Agar ausgemessen und die durch die Präparate hervorgerufene Wachstumshemmung ausgedrückt in %, bezogen auf die Kontrolle (= beimpftem Agar ohne Wirkstoffzusatz r O % Hemmung), bestimmt.The agar was previously in the liquid state that was stressed links in the concentrations given in Table 11 were added. Six days after When the plates were inoculated, the diameter of the fungal colonies on the agar was measured and the inhibition of growth caused by the preparations expressed in%, based on on the control (= inoculated agar without added active ingredient r 0% inhibition).
Tabelle 11
Tabelle 12
Tabelle 13
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US4378373A (en) * | 1978-05-09 | 1983-03-29 | Alfa Farmaceutici S.P.A. | Derivatives of benzoylphenoxyalkanoic acids having normolipemizing activity |
US4431834A (en) * | 1981-04-16 | 1984-02-14 | Imperial Chemical Industries Plc | Herbicidal bicyclic compounds |
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CN105801513B (en) * | 2015-12-10 | 2018-12-07 | 江苏中旗作物保护股份有限公司 | N- with activity of weeding replaces alkyl virtue phenoxy base Propionamides compound and its preparation and application |
CN105669584A (en) * | 2016-03-11 | 2016-06-15 | 李为忠 | High-selectivity herbicide N-substitutive alkyl aryloxy phenoxyl propanamide compound and preparation and application thereof |
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