LU85080A1 - 5-PHENOXYBENZOESAEUR DERIVATIVES OF PENTITES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND THIS CONTAINING AGENT WITH HERBICIDAL ACTION - Google Patents
5-PHENOXYBENZOESAEUR DERIVATIVES OF PENTITES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND THIS CONTAINING AGENT WITH HERBICIDAL ACTION Download PDFInfo
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- LU85080A1 LU85080A1 LU85080A LU85080A LU85080A1 LU 85080 A1 LU85080 A1 LU 85080A1 LU 85080 A LU85080 A LU 85080A LU 85080 A LU85080 A LU 85080A LU 85080 A1 LU85080 A1 LU 85080A1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 125000000913 palmityl 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])([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
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
SCHERING AGSCHERING AG
Gewerblicher Rechtsschutz ^ Die Erfindung betrifft neue 5-Phenoxybenzoe säurederivate von Pentiten, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende Mittel mit herbizider Wirkung.Commercial legal protection ^ The invention relates to new 5-phenoxybenzoic acid derivatives of pentites, processes for the preparation of these compounds and compositions containing them with herbicidal activity.
Benzoe-säurederivate von Pentiten mit biologischer Wirkung 10 sind bisher nicht bekannt geworden.Benzoic acid derivatives of pentites with a biological effect 10 have hitherto not been disclosed.
•i• i
Aufgabe der vorliegenden Erfindung ist die Schaffung neuer Wirkstoffe mit vorteilhdter herbizider Wirkung.The object of the present invention is to create new active compounds having an advantageous herbicidal action.
Diese Aufgabe wird erfindungsgemäß diirch ein Mittel gelöst, das als neue Wirkstoffe mindestens ein 2-Phenoxypropionsäure-derivat von Pentiten der allgemeinen Formel ch - ° - y 20 ! ^ 1This object is achieved according to the invention by an agent which contains at least one 2-phenoxypropionic acid derivative of pentites of the general formula ch - ° - y 20 as new active ingredients! ^ 1
CH - 0 - YCH - 0 - Y
CH - 0 - Y I,CH - 0 - Y I,
I JI J
CH - 0 - Y^ 25 CH2 - 0 - Y5 enthält, in der einer der Substituenten Y die Gruppe 30 U CO -Contains CH - 0 - Y ^ 25 CH2 - 0 - Y5 in which one of the substituents Y contains the group 30 U CO -
-y I I-y I I
. ' p3c - O 0 Q z. 'p3c - O 0 Q z
35 W35 W.
und jeweils zwei der anderen Substituenten Y die Gruppe ! \r\ 4 // Vorstand: Dr. Herbert Asmis · Or. Christian Bruhn Hans-Jürgen Hamann Postanschrift: SCHERING AG - 0-1000 Berlin « Postfach «S0311 1 5 Γ ***» Mit,el*,«nscheid Dr. Horst Witzei Postscftedc^onto: Ber.in-WMt 1175-101. 1W10010 § Vorsitzender des Aufsichtsrats : Dr. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin. Konto-Nf. 106 7006 00. BankMtzahl 100400 00and two of the other substituents Y each represent the group! \ r \ 4 // Board: Dr. Herbert Asmis · Or. Christian Bruhn Hans-Jürgen Hamann Postal address: SCHERING AG - 0-1000 Berlin «PO Box« S0311 1 5 Γ *** »With, el *,« nscheid Dr. Horst Witzei Postscftedc ^ onto: Ber.in-WMt 1175-101. 1W10010 § Chairman of the Supervisory Board: Dr. Edward v. Schwartzkoppen Berlin Commerzbank AG. Berlin. Account Nf. 106 7006 00
SCHERINGAGSCHERINGAG
~7~ Gewerblicher Rechtsschutz 5 \ /-R1~ 7 ~ Intellectual Property Law 5 \ / -R1
/C\H/ C \ H
K2 bedeuten, worin . 10 R^ und R,, gleich oder verschieden sind und jeweils Was serstoff, einen C^-C ^-Alkylrest, einen ein- oder mehrfach durch Halogen, C^-C^-Alkoxy, Phenoxy und/oder Ha-v . logenphenoxy substituierten C^-C^-Alkylrest, einenK2 mean in which. 10 R ^ and R ,, are the same or different and each What is hydrogen, a C ^ -C ^ alkyl radical, one or more times by halogen, C ^ -C ^ alkoxy, phenoxy and / or Ha-v. logenphenoxy substituted C ^ -C ^ alkyl, a
Aryl-C^-C^-alkylrest, einen ein- oder mehrfach durch 15 C^-Cg-Alkyl, Halogen, C^-Cg-Alkoxy, Nitro und/oder Tri- fluormethyl substituierten Aryl-C^-C^-Alkylrest, einen C^-Cg-cycloaliphatischen Kohlenwasserstoffrest, einen aromatischen Kohlenwasserstoffrest oder einen ein- oder mehrfach durch C^-C^-Alkyl, Halogçn, C^Cg-Alkoxy, Nitro 20 und/oder Trifluormethyl substituierten aromatischenAryl-C ^ -C ^ -alkyl radical, an aryl-C ^ -C ^ alkyl radical which is substituted one or more times by 15 C ^ -Cg alkyl, halogen, C ^ -Cg alkoxy, nitro and / or trifluoromethyl , a C ^ -Cg-cycloaliphatic hydrocarbon residue, an aromatic hydrocarbon residue or an aromatic substituted one or more times by C ^ -C ^ alkyl, halogen, C ^ Cg alkoxy, nitro 20 and / or trifluoromethyl
Kohlenwasserstoffrest oder R^ und R^ gemeinsam mit dem angrenzenden C-Atom einen C^-Cg-cycloaliphatischen Kohlenwasserstoffrest darstellen, Z Nitro, Cyan oder Halogen, 25 U Wasserstoff oder Halogen und W Wasserstoff, Halogen, Cyan, Trifluormethyl oder einen C^-C^-Alkylrest bedeuten.Hydrocarbon radical or R ^ and R ^ together with the adjacent carbon atom represent a C ^ -Cg-cycloaliphatic hydrocarbon radical, Z nitro, cyano or halogen, 25 U hydrogen or halogen and W hydrogen, halogen, cyano, trifluoromethyl or a C ^ - C ^ alkyl radical.
Die erfindungsgemäßen Mittel eignen sich überraschenderweise 30 zur Bekämpfung von Unkräutern sogar unter Schonung von Kul turpflanzen und bereichern daher den Stand der Technik auf 15 diesem Gebiet erheblich.The agents according to the invention are surprisingly suitable for combating weeds even with the protection of crop plants and therefore considerably enrich the state of the art in this field.
«*«*
Die erfindungsgemäßen Mittel sind beispielsweise brauchbar ·- 35 zur selektiven Bekämpfung von schwer bekämpfbaren Ungräsem, wie Viola, Galium, Centaurea, Amaranthus, Ipomea, Fagopyrum,The agents according to the invention can be used, for example, for the selective control of grasses which are difficult to control, such as viola, galium, centaurea, amaranthus, ipomea, fagopyrum,
Sesbania, Datura, Chrysanthemum, Polygonum, Matricaria in Kulturen wie Soja, Weizen, Reis, Gerste, Erdnuß und Kartof-./ fei.Sesbania, Datura, Chrysanthemum, Polygonum, Matricaria in crops such as soy, wheat, rice, barley, peanut and potatoes.
1 -8- 3 Vorsitzender des Auleittitsrats: Dr. Eduard v. SdneartZItoopen Beniner Contmenbank AG, Berlin, Konto-Nr. Wtimt&BwiMBM 1 Cd ZOO 001 -8- 3 Chairman of the Board of Directors: Dr. Edward v. SdneartZItoopen Beniner Contmenbank AG, Berlin, account no. Wtimt & BwiMBM 1 Cd ZOO 00
SCHERING AGSCHERING AG
"8“ Gewerblicher Rechtsschutz y 5"8" Intellectual Property Law y 5
Die erfindungsgemäßen Mittel können im·Vorauflaufverfahren, vorzugsweise aber im Nachauflaufverfahren appliziert werden und besitzen vorteilhafterweise schon in niedrigen Aufwandmengen von 0,05 bis 5%0 kg Aktivsubstanz/ha eine gute Wirkung.The agents according to the invention can be applied in the pre-emergence process, but preferably in the post-emergence process, and advantageously have a good effect even at low application rates of 0.05 to 5% 0 kg of active substance / ha.
1010th
Von den erfindungsgemäßen Verbindungen zeichnen sich durch eine optimale Wirkung der bezeichneten Art insbesondere diejenigen aus, bei denen in der allgemeinen Formel 1 R^ und Rg 15 gleich oder verschieden sind und jeweils Wasserstoff, Methyl, Äthyl, Propyl, Isopropyl, n-Butyl, sec.-Butyl, tert.-Butyl, 2,2-Dimethyl-l-propyl, n-Pentyl, n-Heptyl, n-Octyl, n-Decyl, Chlormethyl, Brommethyl, FJuormethyl, Dichlor-methyl, Trifluormethyl, Trichlormethyl, Methoxymethyl, 20 Äthoxymethyl, Phenoxymethyl, 4-Chlorphenoxymethyl, Chlor äthyl, Bromäthyl, 2-Äthoxyäthyl, 2-Phenoxyäthyl, Cyclo-propyl, Cyclopentyl, Cyclohexyl, Benzyl, 2-Phenyläthyl,Of the compounds according to the invention are distinguished by an optimal action of the type specified, in particular those in which R 1 and R 15 in the general formula 1 are identical or different and in each case are hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, sec .-Butyl, tert-butyl, 2,2-dimethyl-l-propyl, n-pentyl, n-heptyl, n-octyl, n-decyl, chloromethyl, bromomethyl, FJuormethyl, dichloromethyl, trifluoromethyl, trichloromethyl, methoxymethyl , 20 ethoxymethyl, phenoxymethyl, 4-chlorophenoxymethyl, chloroethyl, bromoethyl, 2-ethoxyethyl, 2-phenoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, benzyl, 2-phenylethyl,
Phenyl, 2-Chlorphenyl, 3_Chlorphenyl, 4-Chlorphenyl, 3,4-Dichlorphenyl, 4-Methoxyphenyl, 4-Nitrophenyl oder 25 2,^-Dichlorphenyl bedeuten.Phenyl, 2-chlorophenyl, 3_chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 4-methoxyphenyl, 4-nitrophenyl or 25 2, ^ - dichlorophenyl mean.
Erfindungsgemäße Verbindungen mit herausragender Wirkung « sind insbesondere solche, bei denen in der allgemeinen For mel I 30 1) Y^ die Gruppe U CO- cVQ.„.Q.zCompounds according to the invention with outstanding activity are in particular those in which, in the general formula I 30 1) Y ^, the group U CO-cVQ
WW
und Y2 und Y^ zusammen und Y^ und Y,_ zusammen jeweils eine gegebenenfalls substituierte Methylengruppe 4 ^<Rl 2 // Rg darstellen oder .. Vorstand : Or. Herbert Asinis · Dr. Christian Bruhn · Hans-Jürgen Hamann Postanschrift: SCHERINS AQ · 0-1000 Berlin 65· Postfach Mail \ Or. Heinz Hannse · Karl Otto Mittelstenscheid · Or. Horst Witzei Postschedt-Konto: Berlin-West 1175-101. Bankleitzahl 10010010 * Vorsitzender des Aufsichterdts: Or. Eduard v. Scftwartzkoppen Berliner Commerzbank AG. Berlin. Konto-Nr. 1067006 00. Benklfitzihi 10040000 I Sitz der Gesellschaft: Berlin und Bergkamen Κϊϊand Y2 and Y ^ together and Y ^ and Y, _ together represent an optionally substituted methylene group 4 ^ <Rl 2 // Rg or .. Board of Directors: Or. Herbert Asinis · Dr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERINS AQ0-1000 Berlin 65Postbox Mail \ Or. Heinz HannseKarl Otto MittelstenscheidOr. Horst Witzei Postschedt account: Berlin-West 1175-101. Bank code 10010010 * Chairman of the supervisory board: Or. Eduard v. Scftwartzkoppen Berliner Commerzbank AG. Berlin. Account number. 1067006 00. Benklfitzihi 10040000 I Registered office of the company: Berlin and Bergkamen Κϊϊ
SCHERING AGSCHERING AG
-9- Gewerblich·!· Rechtsschutz y « 5 2) Y^ die Gruppe der allgemeinen Formel II und Y^ und Y^ zusammen und Y^ und Y^ zusammen jeweils eine gegebenen*· falls substituierte Methylengruppe oder 3) Yjj die Gruppe der allgemeinen Formel II und Y^ und 10 zusammen und Y^ und Y^ zusammen jeweils eine gegebenen falls substituierte Methylengruppe bedeuten.-9- Commercial ·! · Legal protection y «5 2) Y ^ the group of the general formula II and Y ^ and Y ^ together and Y ^ and Y ^ together each a given * · if substituted methylene group or 3) Yjj the group of general formula II and Y ^ and 10 together and Y ^ and Y ^ together each represent a given optionally substituted methylene group.
„ Die erfindungsgemäßen Verbindungen treten als optische, gege benenfalls auch als geometrische Isomere auf. Die einzelnen *5 Isomeren und ihre Mischungen gehören auch zum Gegenstand der"The compounds of the invention occur as optical, optionally also as geometric isomers. The individual * 5 isomers and their mixtures also belong to the subject of
Erfindung.Invention.
Die erfindungsgemäßen Verbindungen können entweder «Hein, in Mischung miteinander oder mit anderen Wirkstoffen ange-20 wendet werden. Gegebenenfalls können Entblätterungs-, Pflan- zenschutz- oder Schädlingsbekämpfungsmittel je nach dem gewünschten Zweck zugesetzt werden.The compounds according to the invention can either be used in a mixture with one another or with other active compounds. If necessary, defoliants, crop protection agents or pesticides can be added depending on the desired purpose.
Sofern eine Verbreiterung des WirkungsSpektrums beabsichtigt 25 ist, können auch andere Biozide zugesetzt werden. Beispiels weise eigenen sich als herbizid wirksame Mischungspartner diejenigen Wirkstoffe, die in Weed Abstracts, Vol.31» No. 7 1982, tinter dem Titel "List of common names and abbreviations employed for currently used herbicides and plant growth regu-lators in Weed Abstracts" aufgeführt sind.If the spectrum of activity is to be broadened, other biocides can also be added. For example, those active ingredients which are described in Weed Abstracts, Vol.31 »No. 7 1982, behind the title "List of common names and abbreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts".
’ Ä Zweckmäßig werden die erfindungsgemäßen Wirkstoffe oder deren’Ä The active ingredients according to the invention or their
Mischung in Form von Zubereitungen wie Pulvern, Streumitteln,Mix in the form of preparations such as powders, sprinkling agents,
Granulaten, Lösungen, Emulsionen oder Suspensionen unter Zu- 35 satz von flüssigen und/oder festen Trotgerstoffen beziehungsweise Verdünnungsmitteln und gegebenenfalls von Netz-, Haft-, Emulgier-und/oder Dispergierhilfsmitteln, angewandt, vorzugsweise in Form von Emulsionskonzentraten.Granules, solutions, emulsions or suspensions with the addition of liquid and / or solid bulking agents or diluents and, if appropriate, wetting agents, adhesives, emulsifiers and / or dispersing agents, are used, preferably in the form of emulsion concentrates.
, 40 / § " j; Vorstand: Dr. Herbert Asmis · Dr. Christian Bruhn Hans-Jürgen Hamann Postanschrift: SCHERING AQ · D-1000 Berlin AS. Postfach 858311 i °r‘ Tamise · KariOtto Mittelstenscheid · Or. Horst Witzel Postscheck-Konto : Berlin-West 1175-101, Bankleitzahl 10010010 -! Vorsitzender des Aufsichtsrats: Dr. Eduard v. Sehwartzkoppen Berliner Commerzbank AG, Berlin, Konto-Nr.100700600, Bankleitzahl 100400 00 E Sitz der Gesellschaft: Berlin und Bergkamen Berliner Oisconto-Bank AG. Berlin, Konto-Nr.241/5000. Bankleitzahi im70000, 40 / § "j; Board: Dr. Herbert Asmis · Dr. Christian Bruhn Hans-Jürgen Hamann Postal address: SCHERING AQ · D-1000 Berlin AS. Postfach 858311 i ° r 'Tamise · KariOtto Mittelstenscheid · Or. Horst Witzel Postscheck- Account: Berlin-West 1175-101, bank code 10010010 -! Chairman of the supervisory board: Dr. Eduard v. Sehwartzkoppen Berliner Commerzbank AG, Berlin, account no.100700600, bank code 100400 00 E Company headquarters: Berlin and Bergkamen Berliner Oisconto-Bank AG.Berlin, account no.241 / 5000.Bank sorting im70000
SCHERING AGSCHERING AG
” 10“ Gewerblicher Rechtsschutz r 5 Geeignete flüssige Trägerstoffe sind zum Beispiel Wasser, aliphatische und aromatische Kohlenwasserstoffe, wie Benzol, To.1.110, Xylol, Cyclohexanon, Isoplioron, Dimethylsulfoxyd, Dimethylformamid, weiterhin Mineralölfraktionen.”10“ Commercial legal protection r 5 Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as benzene, To.1.110, xylene, cyclohexanone, isopliorone, dimethyl sulfoxide, dimethylformamide and mineral oil fractions.
; 10 Als feste Trägerstoffe eignen sich Mineralerden, zum Beispiel; 10 Mineral earths are suitable as solid carriers, for example
Tonsil, Silicagel, Talkum, Kaolin, Attaclay, Kalkstein, Kieselsäure und pflanzliche Produkte, zum Beispiel Mehle.Tonsil, silica gel, talc, kaolin, Attaclay, limestone, silica and vegetable products, for example flours.
An oberflächenaktiven Stoffen sind zu nennen zum Beispiel ^ Calciumligninsulfonat, Polyoxyäthylen-alkylphenoläther,Examples of surface-active substances include calcium lignin sulfonate, polyoxyethylene alkylphenol ether,
Naphthalinsulfonsäuren und deren Salze, Phenolsulfonsäuren und deren Salze, Formaldehydkondensate, Fettalkoholsulfate sowie substituierte Benzolsulfonsäuren und deren Salze.Naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts.
" «Λ"« Λ
Der Anteil des beziehungsweise der Wirkstoffe(s) in den ver-'schiedenen Zubereitungen kann in weiten Grenzen variieren. Beispielsweise enthalten die Mittel etwa 5 his 95 Gewichtsprozente Wirkstoffe, etwa 95 his 5· Gewichtsprozente flüssige oder feste Trägerstoffe sowie gegebenenfalls bis zu 20 Ge-25 wichtsprozent oberflächenaktive Stoffe.The proportion of the active ingredient (s) in the different preparations can vary within wide limits. For example, the compositions contain about 5 to 95 percent by weight of active ingredients, about 95 to 5 percent by weight of liquid or solid carriers and optionally up to 20 percent by weight of surface-active agents.
Die Ausbringung der Mittel kann in üblicher Weise erfolgen, \ zum Beispiel mit Wasser als Träger in Spritzbrühmengen von 30 etwa 100 bis 1000 Liter /ha. Eine Anwendung der Mittel im sogenannten Low-Volume- und Ultra-Low-Volume-Verfahren ist . n ebenso möglich wie ihre Applikation in Form von sogenanntenThe agents can be applied in a customary manner, for example using water as a carrier in spray liquor amounts of about 100 to 1000 liters / ha. The funds are used in the so-called low-volume and ultra-low-volume process. n just as possible as their application in the form of so-called
Mikrogranulaten.Microgranules.
Λ 35 Zur Herstellung der Zubereitungen werden zum Beispiel die folgenden Bestandteile eingesetzt: koi l — -11- w c Vorstand: Dr. Herbert Asmis · Dr. Christian Bruhn · Hans-Jürgen Hamann Postanschrift: SCHERING AG · 0-1000 Bwtln OS- Poetisch 680311 i Dr. Hemz Hanns. . Karl Otto Mittelstensche.d · Dr. Horst Witz.l Postsöiedc-Konto : B.rlin-W.St 1175-101, B»kMtahl 10010010 — Vorsitzender des Aufsichtsrats: Dr. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin, Konto-Nr. 108700600 Benkleitzahl 10040000 e Sitz der Gesellschaft: Berlin und Bergkamen Berliner Oisconto-Btnk AG. Berlin. Konto-Nr. 241/5008. Benkleitzahl 10070000Λ 35 For example, the following ingredients are used to prepare the preparations: koi l - -11- w c Board: Dr. Herbert AsmisDr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AG0-1000 Bwtln OS- poetic 680311 i Dr. Hemz Hanns. . Karl Otto Mittelstensche. Dr. Horst Witz.l Postsöiedc account: B.rlin-W.St 1175-101, B »kMtahl 10010010 - Chairman of the Supervisory Board: Dr. Edward v. Schwartzkoppen Berlin Commerzbank AG. Berlin, account no. 108700600 Benkleitzahl 10040000 e Registered office of the company: Berlin and Bergkamen Berliner Oisconto-Btnk AG. Berlin. Account number. 241/5008. Benkleitzahl 10070000
SCHERING AGSCHERING AG
”ü” Gewerblicher Rechtsschutz * 5 Λ · Snritzpulver a) 40 Geivichtsprozent Wirkstoff 25 Gewichtsprozent Tonmineralien 20 Gewichtsprozent kolloidale Kieselsäure 10 10 Gewichtsprozent Zellpech 5 Gewichtsprozent oberflächenaktive Stoffe auf der”Ü” Commercial legal protection * 5 Λ · Carving powder a) 40% by weight active ingredient 25% by weight clay minerals 20% by weight colloidal silica 10 10% by weight cell pitch 5% by weight surfactants on the
Basis einer Mischung des Calciumsalzes der Ligninsulfonsäure mit Alkylphenolpolyglycoläthern 15 b) 25 Gewichtsprozent Wirkstoff 60 Gewichtsprozent Kaolin 10 Gewcihtsprozent kolloidale Kieselsäure 5 Gewcihtsprozent oberflächenaktive Stoffe auf Basis 20 des Natriumsalzes des N-Methyl-N- 4 oleyl-taurins und des Calciumsalzes der Ligninsulfonsäure c) l 10 Gewichtsprozent Wirkstoff 25 60 Gewichtsprozent Tonmineralien 15 Gewichtsprozent kolloidale Kieselsäure 10 Gewichtsprozent Zellpech 5 Gewichtsprozent oberflächenaktive Stoffe auf Basis des Natriumsalzes des N-Methyl-N- 30 - oleyl-taurins und des Calciumsalzes der Ligninsulfonsäure * ' B. Paste 4 ^ ^5 Gewichtsprozent Wirkstoff 5 Gewichtsprozent Natriumaluminiumsilikat 15 Gewichtsprozent Cetylpolyglykoläther mit 8 Mol ' · Äthylenoxid 2 Gewichtsprozent Spindelöl 10 Gewichtsprozent Polyäthylenglykol 2 23 Teile Wasser. -12- ! L— / '-Vorstand: Or. Herbert Asmi« · Dr. Christian Bruhn · Hans-Jürgen Hamann Postanschrift: SCHERING AG · 0-1000 Berlin 65 · Poetfadi 650111 i ! Or. Heinz Hannse - Karl Otto Mittelstenscheid Dr. Horst Witzei . Postscheck-Konto : Berlin-West 1175-101, BankMtzahl 10010016 -S Vorsitzender des Aufsichtsrats : Or. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin. Konto-Nr. 10B 7008 00. Banideitztfil 100 400 00 e ' Sitz der Gaunerhaft· Radin und Berliner Diaeonto-BankAG, Berlin, Konto-Nr. 241/5006. Benkfeftzahl 10070000Based on a mixture of the calcium salt of lignosulfonic acid with alkylphenol polyglycol ethers 15 b) 25 percent by weight of active ingredient 60 percent by weight of kaolin 10 percent by weight of colloidal silica 5 percent by weight of surfactants based on 20 the sodium salt of N-methyl-N-4 oleyl-taurine and the calcium salt of ligninsulfonic acid c) 10% by weight of active ingredient 25 60% by weight of clay minerals 15% by weight of colloidal silica 10% by weight of cell pitch 5% by weight of surfactants based on the sodium salt of N-methyl-N-30-oleyl-taurine and the calcium salt of lignosulfonic acid * 'B. Paste 4 ^ ^ 5% by weight of active ingredient 5 percent by weight sodium aluminum silicate 15 percent by weight cetyl polyglycol ether with 8 moles of ethylene oxide 2 percent by weight spindle oil 10 percent by weight polyethylene glycol 2 23 parts water. -12-! L— / 'Board: Or. Herbert Asmi «· Dr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AG0-1000 Berlin 65Poetfadi 650111 i! Or. Heinz Hannse - Karl Otto Mittelstenscheid Dr. Horst Witzei. Postal check account: Berlin-West 1175-101, bank account number 10010016 -S Chairman of the supervisory board: Or. Eduard v. Schwartzkoppen Berlin Commerzbank AG. Berlin. Account number. 10B 7008 00. Banideitztfil 100 400 00 e 'headquarters of crook · Radin and Berliner Diaeonto-Bank AG, Berlin, account no. 241/5006. Benkfeft number 10070000
SCHERINGAGSCHERINGAG
“12- Gwrarblichw Rechtsschutz p 5 C. Emulsionskonzentrat a) 25 Gewichtsprozent Wirkstoff 15 Gewichtsprozent Cyclohexanon 55 Gewichtsprozent Xylol 10 5 Gewichtsprozent Mischung von Nonylphenylpolyoxyäthylen oder Calcivundodecylbenzolsulfonat b) 10 Gewichtsprozent Wirkstoff 6 Gewichtsprozent Cyclohexanon 36 Gewichtsprozent Xylol , 12 Gewichtsprozent Mischling von Nonylphenylpolyoxyäthylen oder Calciumdodecylbenzolsulfonat 36 Gewichtsprozent Mineralöl ait hohea Paraffingehalt“12- Gwrarblichw legal protection p 5 C. Emulsion concentrate a) 25 percent by weight of active ingredient 15 percent by weight of cyclohexanone 55 percent by weight of xylene 10 5 percent by weight of mixture of nonylphenylpolyoxyethylene or calcivundodecylbenzenesulfonate b) 10 percent by weight of active ingredient 6 percent by weight of cyclohexanone 36 percent by weight of xylene, 12 percent by weight of mixed compound of nonylphenylzolonylolonylolonylolonylolonylolonylolonylolonylolonylolonylolonylolonylolonylolonylolonylolonol or 36 percent by weight Mineral oil with a high paraffin content
Die neuen erfindungsgemäßen Verbindungen der allgemeinen 20 Formel 1 lassen sich zum Beispiel herstellen, inddm man a) Verbindungen der allgemeinen Formel CH- - 0 - Y' I 2 1 ÇH - 0 - Y'2 25 CH -0-Υ·3 π CH - 0 - Y ' ^ CH2 “ 0 - Y’5 in der einer der Substituenten Y' Wasserstoff und jeweils 30 zwei der anderen Substituenten Y' die Gruppe \-^Rl bedeuten, mit Verbindungen der allgemeinen Formel 35 u co-xThe new compounds of the general formula 1 according to the invention can be prepared, for example, by a) compounds of the general formula CH- - 0 - Y 'I 2 1 HH - 0 - Y'2 25 CH -0-Υ · 3 π CH - 0 - Y '^ CH2 “0 - Y'5 in which one of the substituents Y' is hydrogen and in each case two of the other substituents Y 'are the group \ - ^ Rl, with compounds of the general formula 35 u co-x
ko Wko W
2 A-^· -13- 2 - Vorstand : Or. Harbart Asmis · Dr. Christian Bruhn · Hans-Jürgen Hamann Postanschrift : SCHERING AG · 0-1000 Berlin a. Postfach a β 11 2 Or. Heinz Hannse · Karl Otto Mittelstenscheid · Dr. Horst Witzei Postscheck-Konto: Berlin-West 1175-101. Banktoltzahl 10010010 ; .? Vorsitzender des Autsichtsrais: Dr. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin. Konto-Nr. 10*700800. Banideitzahl 100400002 A- ^ · -13- 2 - Board: Or. Harbart Asmis · Dr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AG0-1000 Berlin a. PO Box a β 11 2 Or. Heinz Hannse · Karl Otto Mittelstenscheid · Dr. Horst Witzei postal check account: Berlin-West 1175-101. Bank tolts 10010010; .? Chairman of the Supervisory Board: Dr. Edward v. Schwartzkoppen Berlin Commerzbank AG. Berlin. Account number. 10 * 700800. Banideit number 10040000
SCHERING AGSCHERING AG
~ 13” Gewerblicher Rechtsschutz r - gegebenenfalls in Gegenwart von säurebindenden Mitteln und/oder eines Katalysators reagieren läßt oder b) Verbindungen der allgemeinen Formel CK2-0-Y"i 10 <jH - 0 - Y " 2 CH - 0 - Y" j IV, CH - 0 - Y·' , I 4 CH2- o - Y· in der einer der Substituenten Y'' die Gruppe CO - H° -O" 20 und jeweils zwei der anderen Substituenten Y* ' die Gruppe \C/Rl~ 13 ”Industrial property protection r - if appropriate in the presence of acid-binding agents and / or a catalyst, or b) compounds of the general formula CK2-0-Y" i 10 <jH - 0 - Y "2 CH - 0 - Y" j IV, CH - 0 - Y · ', I 4 CH2- o - Y · in which one of the substituents Y' 'is the group CO - H ° -O "20 and two of the other substituents Y *' are the group \ C / Rl
bedeuten, mit Verbindungen der allgemeinen Formel 25 Umean with compounds of general formula 25 U
JJ
CP3-<Q>-XCP3- <Q> -X
w 30 in Gegenwart von säurebindenden Mitteln und/oder einesw 30 in the presence of acid-binding agents and / or one
Katalysators reagieren läßt, Worin R^, Rg, Z, U und W die ^ oben genannte Bedeutung haben und X ein Halogenatom, vor zugsweise ein Chlor- oder Bromatom, darstellen.Catalyst can react, in which R ^, Rg, Z, U and W have the ^ meaning given above and X represents a halogen atom, preferably a chlorine or bromine atom.
35 Die Umsetzung der Reaktionspartner erfolgt zwischen - 10 und 150 °C, im allgemeinen jedoch zwischen Raumtemperatur und Rückflußtemperatur des entsprechenden Reaktionsgemisches. Die Reaktionsdauer beträgt 1 bis 72 Stunden. In der Regel erfolgt die Reaktion bei Normaldruck oder leichtem Überdruck.35 The reaction of the reactants takes place between - 10 and 150 ° C, but generally between room temperature and the reflux temperature of the corresponding reaction mixture. The reaction time is 1 to 72 hours. As a rule, the reaction takes place at normal pressure or slightly positive pressure.
«7 Zur Synthese der erfindungsgemäßen Verbindungen werden die ? /L~ -14- . / Vorstand: Dr. Herbert Asmis Or. Christian Bruhn · Hans-Jürgen Hamann Postanschrift: SCHERING A3 D-1000 Berlin 05· PostfachIS0311 j °r' H°rS* WltZ*‘ Postsehedt-Konto : Berlin-Weet 1175-101, Banfctettzahi 1« 10010 4 Vorsitzender des Aufsiehtsrats: Dr, Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin. Konto-Nr. 10070»00, BanklettzWk 10040000 g Sitz der Gesellschaft: Berlin und Bergkamen Berliner Diseonto-Bank AG, Berlin, Konto-Nr.241/5000, Bankleitzahl 10070000 5 Handelsregister: AG Charlottenburg 33 HRB 283 u. AG Kamen HRB 0061 Berliner Handels-Gesellschaft — Frankfurter Bank —, Berlin,«7 For the synthesis of the compounds according to the invention, the? / L ~ -14-. / Board: Dr. Herbert Asmis Or. Christian Bruhn · Hans-Jürgen Hamann Postal address: SCHERING A3 D-1000 Berlin 05 · PostfachIS0311 j ° r 'H ° rS * WltZ *' Postsehedt account: Berlin-Weet 1175-101, Banfctettzahi 1 «10010 4 Chairman of the supervisory board: Dr, Eduard v. Schwartzkoppen Berlin Commerzbank AG. Berlin. Account number. 10070 »00, BanklettzWk 10040000 g Registered office: Berlin and Bergkamen Berliner Diseonto-Bank AG, Berlin, account no.241 / 5000, bank code 10070000 5 Commercial register: AG Charlottenburg 33 HRB 283 u. AG Kamen HRB 0061 Berliner Handels-Gesellschaft - Frankfurter Bank -, Berlin,
j · . SCHERINGAGj ·. SCHERINGAG
Gewerblicher Rechtaadurtz r 5 Reaktanden in etwa äquimolaren Mengen eingesetzt. GeeigneteCommercial Rechtaadurtz r 5 reactants used in approximately equimolar amounts. Suitable
Reaktionsmedien sind gegenüber den Reaktanden inerte Lösungsmittel. Die Wahl der Lösungs- beziehungsweise Suspensionsmittel richtet sich nach dem Einsatz der entsprechenden Alkyl- beziehungsweise Acylhalogenide und der angewandten Säureakzeptoren. Als Lösungs- beziehungsweise Suspensionsmittel seien beispielsweise genannt, aliphatische und aromatische Kohlenwasserstoffe wie Petroläther, Cyclohexan, Hexan, Heptan, Benzol, Toluol, Xylole; halogenierte Kohlenwasserstoffe wie Methylenchlorid, Äthylenchlorid, Chlorbenzol, Chloroform, Tetrachlorkohlenstoff, Tetrachloräthylen; Äther wie Diäthyläther, Diisopropyläther, Anisol, Dioxan, Tetrahydrofuran; Carbonsäurenitril· wie Acetonitril, Propionitril; Carbonsäureamide wie Dimethylformamid; Dimethylsulfoxid;Reaction media are solvents which are inert to the reactants. The choice of solvents or suspending agents depends on the use of the corresponding alkyl or acyl halides and the acid acceptors used. Examples of solvents or suspending agents are aliphatic and aromatic hydrocarbons such as petroleum ether, cyclohexane, hexane, heptane, benzene, toluene, xylenes; halogenated hydrocarbons such as methylene chloride, ethylene chloride, chlorobenzene, chloroform, carbon tetrachloride, tetrachlorethylene; Ethers such as diethyl ether, diisopropyl ether, anisole, dioxane, tetrahydrofuran; Carbonitrile · such as acetonitrile, propionitrile; Carboxamides such as dimethylformamide; Dimethyl sulfoxide;
Ketone wie Aceton, Diäthylketon, Methyläthylketon; Alkohole 20 wie Methanol, Äthanol, Propanol, Butanol und Gemische solcher Lösungsmittel untereinander. In einigen Fällen kann auch der Reaktionspartner selbst als Lösungsmittel dienen.Ketones such as acetone, diethyl ketone, methyl ethyl ketone; Alcohols 20 such as methanol, ethanol, propanol, butanol and mixtures of such solvents with one another. In some cases, the reactant itself can also serve as a solvent.
Als Säureakzeptoren eignen sich organische Basen, wie zum Beispiel Triäthylamin, Trimethylamin, N/N-Dimethylanilin, Pyridin und Pyridinbasen (^-Dimethylaminopyridin) oder anorganische Basen wie Oxide, Hydroxide, Carbonate, Hydrogen-carbonate und Alkoholate von Alkali- und Erdalkalimetall sowie Alkalisalze von Carbonsäuren (KOH, NaOH, Na_C0_, 30 * 3 CH^COONa).Suitable acid acceptors are organic bases, such as, for example, triethylamine, trimethylamine, N / N-dimethylaniline, pyridine and pyridine bases (^ -dimethylaminopyridine) or inorganic bases such as oxides, hydroxides, carbonates, hydrogen carbonates and alcoholates of alkali and alkaline earth metal and alkali metal salts of carboxylic acids (KOH, NaOH, Na_C0_, 30 * 3 CH ^ COONa).
Flüssige Basen wie Pyridin können gleichzeitig als Lösungs-K mittel eingesetzt werden. Entstehender Halogenwasserstoff kann in manchen Fällen auch mittels Durchleiten von Inert-gas, zum Beispiel Stickstoff, aus dem Reaktionsgemisch entfernt werden oder an Molekularsieb absorbiert werden.Liquid bases such as pyridine can be used as a solvent K at the same time. In some cases, hydrogen halide formed can also be removed from the reaction mixture by passage of inert gas, for example nitrogen, or it can be absorbed on molecular sieve.
Die Gegenwart eines Reaktionskatalysators kann von Vorteil sein. Als Katalysatoren sind Kaliumjodid und Oniumverbindun- kOji gen geeignet, wie quaternäre Ammonium-, Phosphonium- und « /' c /[ Arsöniumverbindungen sowie Sulfoniumverbindungen. Ebenfalls à ’ ( VoratßrttfTor. Herbert Asmia · Dr. Christi«) Bruhn Hans-JQrgen Hamann Postanschrift: SCHERING AQ * 0*1000 Berlin IS · Poatfadi 650311 1 /Sri"2, T“; . ' Dr· HOr*‘WiUel Poetscheek-Konfo: Bertta-weet 1175-101. BankMtzahf 10010010 Î Vorsitzender des Aufsichtsrats: Dr. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Barlin. Konto-Nr. 10*700600, BanMettzahl 100400 00 E Sitz der Gesellschaft: Berlin und Bergkamen Berliner Disconto-BankAG. Berlin, Konto-Nr.2*1/500·. BankieitzaM 10070000 o Handelsregister: AG Charlottenburg 93 HRB 2S3 u. AG Kamen HRB 0061 Berliner Handels-Geeelladieft — Frankfurter Bank —, Berlin,The presence of a reaction catalyst can be advantageous. Potassium iodide and onium compounds are suitable as catalysts, such as quaternary ammonium, phosphonium and «/ 'c / [arsonium compounds and sulfonium compounds. Also à '(VoratßrttfTor. Herbert Asmia · Dr. Christi «) Bruhn Hans-JQrgen Hamann Postal address: SCHERING AQ * 0 * 1000 Berlin IS · Poatfadi 650311 1 / Sri" 2, T “;.' Dr · HOr * 'WiUel Poetscheek -Confo: Bertta-weet 1175-101.BankMtzahf 10010010 Î Chairman of the supervisory board: Dr. Eduard v. Schwartzkoppen Berliner Commerzbank AG.Barlin.Account No. 10 * 700600, BanMett number 100400 00 E Company headquarters: Berlin and Bergkamen Berliner Disconto -BankAG.Berlin, account no.2 * 1 / 500BankieitzaM 10070000 o Commercial register: AG Charlottenburg 93 HRB 2S3 and AG Kamen HRB 0061 Berliner Handels-Geeelladieft - Frankfurter Bank -, Berlin,
SCHERING AGSCHERING AG
“15“ Gewerblicher Rechtsschutz * 5 geeignet sind Polyglykoläther, insbesondere cyclische, wie j zum Beispiel l8-Krone-6, und tertiäre Amine, wie zum Bei- • spiel Tributylamin. Bevorzugte Verbindungen sind quaternäre"15" Industrial property protection * 5 suitable are polyglycol ethers, especially cyclic ones, such as j, for example, 18-crown-6, and tertiary amines, such as tributylamine. Preferred compounds are quaternary
Ammoniumverbindungen, wie zum Beispiel Benzyltriäthylammonium-Chlorid und Tetrabutylammoniumbromid.Ammonium compounds such as benzyltriethylammonium chloride and tetrabutylammonium bromide.
1010th
Die nach oben genannten Verfahren hergestellten erfindungsgemäßen Verbindungen können auch nach den üblichen Verfahren aus dem Reaktionsgemisch isoliert werden, beispielsweise durch Abdestillieren des eingesetzten Lösungsmittels bei 15 normalem oder vermindertem Druck, durch Ausfällen mit Wasser oder durch Extraktion. Ein erhöhter Reinheitsgrad kann in der Regel durch säulenchromatographische Aufreinigung sowie durch fraktionierte Destillation erhalten werden.The compounds according to the invention prepared by the abovementioned processes can also be isolated from the reaction mixture by the customary processes, for example by distilling off the solvent used at normal or reduced pressure, by precipitation with water or by extraction. An increased degree of purity can generally be obtained by purification by column chromatography and by fractional distillation.
20 Die erfindungsgemäßen Verbindungen stellen in der Regel 'fast färb- und geruchlose Flüssigkeiten aber auch zum Teil kristalline Körper dar, die schwerlöslich in Wasser, bedingt löslich in aliphatischen Kohlenwasserstoffen wie Petroläther, Hexan, Pentan und Cyclohexan, gut löslich in halogenierten Kohlenwasserstoffen wie Chloroform, Methylenchlorid und Tetrachlorkohlenstoff, aromatischen Kohlenwasserstoffen wie Benzol, Toluol -und Xylol,Äther, wie Diäthyläther, Tetrahydrofuran und Dioxan, Carbonsäurenitrilen wie Acetonitril,The compounds according to the invention are generally 'almost colorless and odorless liquids but also partly crystalline bodies which are sparingly soluble in water, to a limited extent soluble in aliphatic hydrocarbons such as petroleum ether, hexane, pentane and cyclohexane, readily soluble in halogenated hydrocarbons such as chloroform, Methylene chloride and carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene and xylene, ethers such as diethyl ether, tetrahydrofuran and dioxane, carbonitriles such as acetonitrile,
Ketonen wie Aceton, Alkoholen wie Methanol und Äthanol, 30Ketones such as acetone, alcohols such as methanol and ethanol, 30
Carbonsaureamiden wie Dimethylformamid und Sulfoxide wie Dimethylsulfoxid sind.Carboxylic acid amides such as dimethylformamide and sulfoxides such as dimethyl sulfoxide.
* v* v
Die Ausgangsverbindungen zur Herstellung der erfindungsgemäßen Verbindungen sind an sich bekannt oder können nach an 35 sich bekannten Verfahren hergestellt werden.The starting compounds for the preparation of the compounds according to the invention are known per se or can be prepared by processes known per se.
Die folgenden Beispiele erläutern die Herstellung der erfin-dungsgemäßen Pentitester.The following examples illustrate the preparation of the pentite esters according to the invention.
i TL ·16' £ Vorstand: Dr. Herbert Asmis · Dr. Christian Bruhn · Hans-Jürgen Hamann Postanschrift: SCHERINQ AG · D-1000 Berlin OS- Poetfach<6 0311 i Dr. Haina Hanns· · Karl Otto Mittelstenscheid · Qr. Horst Witzei Poatscheek-Konto : Berlin-West 1175-101, Bankleitzahl 10010010 - Vorsitzender des Aufsichtsrats: Dr. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin, Konto-Nr. 10S 7008 00. BsnkleitzaM 10040000 e Sitz der Gesellschaft- Berlin nnri R.rnk.m.n Berliner Disconto-Bank AG. Berlin. Konto-Nr.241/500B. Bankleitzahl 10070000 (ii TL16 '£ Board: Dr. Herbert AsmisDr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERINQ AGD-1000 Berlin OS- Poetfach <6 0311 i Dr. Haina HannsKarl Otto MittelstenscheidQr. Horst Witzei Poatscheek account: Berlin-West 1175-101, bank code 10010010 - Chairman of the Supervisory Board: Dr. Edward v. Schwartzkoppen Berlin Commerzbank AG. Berlin, account no. 10S 7008 00. BsnkleitzaM 10040000 e Registered office of the company- Berlin nnri R.rnk.m.n Berliner Disconto-Bank AG. Berlin. Account No. 241 / 500B. Bank code 10070000 (i
SCHERING AGSCHERING AG
-16- Gewerblicher Rechtsschutz r 5 BEISPIEL 1 5-0-/5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoyl7-„ 1,2: 314-bis-O-(isopropyliden)-xylit 10 40,0 g (0,172 Mol) 1,2: 3»4-Bis-O-(isopropyliden)-xylit werden in 250 ml Methylenchlorid vorgelegt und bei 20°C '] mit 17,3 g (0,172 Mol) Triäthylamin versetzt. Anschließend tropft man hierzu unter Eiskühlung bei 20°C eine Lösung aus 15 65,3 g (0,172 Mol) 5-(2-Chlor-4-trifluormethyl-phenoxy)-2- nitro-benzoylchlorid in 100 ml Methylenchlorid. Es wird noch eine Stunde bei Ratuntemperatur nachgerührt. Anschließend wird das Reaktionsgemisch dreimal mit je 250 ml Vasser gewaschen. Nach Trocknung der Methylenchloridphase über Mag-20 nesiumsulfat wird filtriert und das Lösungsmittel abgezogen.-16- Intellectual Property Rights r 5 EXAMPLE 1 5-0- / 5- (2-Chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoyl7- "1,2: 314-bis-O- (isopropylidene) xylitol 10 40.0 g (0.172 mol) of 1.2: 3 '4-bis-O- (isopropylidene) xylitol are placed in 250 ml of methylene chloride and 17.3 g (0.172 mol) of triethylamine are added at 20.degree . A solution of 15 65.3 g (0.172 mol) of 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoyl chloride in 100 ml of methylene chloride is then added dropwise with ice cooling at 20 ° C. The mixture is stirred for another hour at ratun temperature. The reaction mixture is then washed three times with 250 ml of water. After drying the methylene chloride phase over magnesium sulfate, the mixture is filtered and the solvent is stripped off.
Das zurückbleibende Öl wird mit 500 ml heißem Hexan digeriert und darauf die fiexanphase wiederum eingeengt. Das so wiederum erhaltende Öl wird bei 50°C/0,1 Torr getrocknet und kristalliert dann allmählich.The remaining oil is digested with 500 ml of hot hexane and then the fiexan phase is again concentrated. The oil thus obtained is dried at 50 ° C / 0.1 Torr and then gradually crystallizes.
25 Ausbeute: 6l,2 g = 62,4 % der Theorie25 Yield: 6l, 2 g = 62.4% of theory
Fp.: 100 - 102°CMp .: 100-102 ° C
DC : Laufmittel = Toluol/Essigester (l:l) R^-Wert: 0,6lDC: mobile phase = toluene / ethyl acetate (l: l) R ^ value: 0.6l
Analyse: Berechnet C 52,1394 H 4,3794 N 2,4394 CI 6,1594 30 Gefunden C 52,28?4 H 4,2794 N 2,6696 CI 6,4994 s V.Analysis: Calculated C 52.1394 H 4.3794 N 2.4394 CI 6.1594 30 Found C 52.28? 4 H 4.2794 N 2.6696 CI 6.4994 s V.
35 / -17- 4o Λ-- er» Ψ» l. Vorstand: Dr. Herbert Asmis · Dr. Christian Bruhn · Hans-Jürgen Hamann Postanschrift: SCHERING AG - D-1000 Berlin 65· Postfach 6S0311 1 Or. Heinz Hannse · Karl Otto Mittelstenscheid Dr.Horst Witzel Postscheck-Konto: Berlin-West 1175-101, Bankleitzmltl 10010010 * Vorsitzender des Aufsichtsrats: Dr. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin. Konto-Nr. 1070000, Bankfeitzahl 10040000 2 cn. j.. a...it.^.u. ____à n______ Rnrlinor Diseflnto.Bsnk AG Radin KnntnJJr 9i1/S1Di Ranirlaitrahl immm35 / -17- 4o Λ-- er »Ψ» l. Board: Dr. Herbert AsmisDr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AG - D-1000 Berlin 65Postbox 6S0311 1 Or. Heinz HannseKarl Otto Mittelstenscheid Dr.Horst Witzel Postal check account: Berlin-West 1175-101, bank routing 10010010 * Chairman of the Supervisory Board : Dr. Edward v. Schwartzkoppen Berlin Commerzbank AG. Berlin. Account number. 1070000, bank number 10040000 2 cn. j .. a ... it. ^. u. ____ à n______ Rnrlinor Diseflnto.Bsnk AG Radin KnntnJJr 9i1 / S1Di Ranirlaitrahl immm
SCHERING AGSCHERING AG
-17“ Gewerblicher Rechtsschutz *· 5 In analoger Weise lassen sich die weiteren erfindungsgemäßen-17 "Commercial legal protection * · 5 The other inventive can be analogously
Verbindungen hersteilen.Make connections.
Beispiel Name der Verbindung Physikalische _Konstante_ 10 2 1-0-/5-(2-Chlor-4-trifluormethyl-phenoxy)- 2-nitrobenzoyl7-2,3î4,5-bis-0-isopropyl-iden-D-arabit" “d20:1,5067 3 3-0—/5-(2-Chlor-^-trifluormethyl-phenoxy)-2-nitrobenzoyl7-1 , 2 ;4,5- bis-0-isopropyliden-adönit n^20:1,5040 15 4 5-0-/3-(2-Chlor-^-trifluormethyl- phenöxy) -2-nitro-benzoyl7-1 » 2:3 » 4- 0Example Name of the compound Physical _constant_ 10 2 1-0- / 5- (2-chloro-4-trifluoromethyl-phenoxy) - 2-nitrobenzoyl7-2,3î4,5-bis-0-isopropyl-iden-D-arabite "" d20: 1.5067 3 3-0- / 5- (2-chloro - ^ - trifluoromethyl-phenoxy) -2-nitrobenzoyl7-1, 2; 4,5- to-0-isopropylidene adonite n ^ 20: 1, 5040 15 4 5-0- / 3- (2-chloro - ^ - trifluoromethyl-phenoxy) -2-nitro-benzoyl7-1 »2: 3» 4- 0
bis-0-/'(4-chlorphenyl)-methylen7-xyüt Fp.: 173 Cbis-0 - / '(4-chlorophenyl) -methylen7-xyüt Mp .: 173 C
5 5-0-/5-(2-Chlor-4-trifluormethyl-phenöxy)-2-nitro-benzoyl7-1»2: 3 » 4- 2q bis-0-(chlormethyl-methÿlen)-xylit n^20:1,5309 • 6 5-0-/5-(2-Chlor-4-trifluormethyl- phenöxy)-2-nitro-benzoyl7-1,2: 314- bis-0-(methyl-octyl-methylen)-xylit nD20:1»^998 7 5-0-/5-(2-Chlor-4-trifluormethyl-25 phenoxy)-2-nitrobenzoylJ-1,2:3»4- bis-0-(äthylmethyImethylen)-xylit nD2®: *»5191 ® 5-0-£5-(2-Chlor-4-trifluormethyl- phenoxy)-2-nitrobenzoylJ -1,2:3,4- bis-0-(diäthylmethylen)-xylit n^20:1 » 51235 5-0- / 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoyl 7-1 »2: 3» 4- 2q bis-0- (chloromethyl-methylene) -xylitol n ^ 20: 1.5309 • 6 5-0- / 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoyl7-1.2: 314- bis-0- (methyloctylmethylene) xylitol nD20 : 1 »^ 998 7 5-0- / 5- (2-chloro-4-trifluoromethyl-25 phenoxy) -2-nitrobenzoylJ-1,2: 3» 4- to-0- (ethylmethylmethylene) -xylitol nD2®: * »5191 ® 5-0- £ 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoylJ -1,2: 3,4- bis-0- (diethylmethylene) -xylitol n ^ 20: 1» 5123
3<I3 <I
9 5-0-C5-(2-Chldr-4-trifluormethyl- • », phenoxy)-2-nitrobenzoyl3-1,2: 3,4- o9 5-0-C5- (2-Chldr-4-trifluoromethyl- • », phenoxy) -2-nitrobenzoyl3-1.2: 3.4- o
bis-0-(methyImethylen)-xylit Fp.: 66-67 Cbis-0- (methylene) xylitol mp: 66-67 ° C
^ Die folgenden Beispiele erläutern die Anwendungsmöglich keiten der erfindungsgemäßen Verbindungen, die in Form der oben angegebenen Zubereitungen erfolgte.^ The following examples illustrate the possible uses of the compounds according to the invention, which was carried out in the form of the preparations indicated above.
i 40/L ’ -18- £ Vorstand: Dr. Herbert Asmis Dr. Christian Bruhn · Hans-Jürgen Hamann Postanschrift: SCHERING AG · 0-1000 Berlin 08 · Postfach 080311 ? - tr. Heinz Hannse · Karl Otto Mittelstenacheid · Dr. Horst Witzei Postscheck-Konto : Berlin-West 1175-101. Bankteitzahi 10010010 * Vorsitzender des Aufsichtsrats ; Dr. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin. Konto-Nr. 108 7008 00. BanfclattzWil 100 400 00 1 Sit. H.r R.«aii*rh.tt- s.riin unH rwniram.n Berliner Disconto-Bank AG. Berlin. Konto-Nr.241/500a. BankiattzaM 10070000i 40 / L ’-18- £ Board: Dr. Herbert Asmis Dr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AG0-1000 Berlin 08Pox 080311? - tr. Heinz Hannse · Karl Otto Mittelstenacheid · Dr. Horst Witzei postal check account: Berlin-West 1175-101. Bankteitzahi 10010010 * Chairman of the Supervisory Board; Dr. Edward v. Schwartzkoppen Berlin Commerzbank AG. Berlin. Account number. 108 7008 00. BanfclattzWil 100 400 00 1 Sit. H.r R. «aii * rh.tt- s.riin unH rwniram.n Berliner Disconto-Bank AG. Berlin. Account no.241 / 500a. BankiattzaM 10070000
SCHERING AGSCHERING AG
-18- Gewerblicher Rechtsschutz t 5 BEISPIEL m-18- Intellectual Property Rights t 5 EXAMPLE m
Im Gewächshaus wurden die in der Tabelle aufgeführten erfindungsgemäßen Verbindungen in einer Aufwandmenge von 3*0 kg Wirkstoff/ha emulgiert in 500 Liter Wasser/ha, auf Viola, und Matricaria als Testpflanzen im Vor- und Nachauflaufver- 10 fahren gespritzt. 3 Wochen nach der Behandlung wurde das Behandlungsergebnis bonitiert, wobei 0 = keine Wirkung und 4 = Vernichtung der Pflanzen bedeutet. Wie aus der Tabelle ersichtlich wird, wurde in 15 der Regel eine Vernichtung der Testpflanzen erreicht.In the greenhouse, the compounds according to the invention listed in the table were sprayed at a rate of 3 * 0 kg of active ingredient / ha emulsified in 500 liters of water / ha, on viola, and matricaria as test plants in the pre- and post-emergence process. The treatment result was rated 3 weeks after the treatment, 0 = no effect and 4 = destruction of the plants. As can be seen from the table, the test plants were generally destroyed in 15.
- 2q Erfindungsgemäße VORAUFLAUF NACHAUFLAUF- 2q PRE-COLLAR according to the invention
Verbindungen Viola/Matri- Viola/Matri- ._caria_caria_ 5-0-/5-(2-Chlor-4-trifluor-methÿl-phenoxy)-2-nitro-benzoyl/-1,2:314-bis-0- 25 (isopröpyliden)-xylit 4 4 4 4 1-0-/5-(2-Chlor-4-trifluor-methÿl-phenoxy)-2-nitro-benzoyl7-2,3:4,5-bis-0- isopropyliden-D-arabit 4 4 4 4 3-0-/5-(2-Chlor-4-trifluor-methyl-phenoxy)-2-nitro- benzoyl7-1,2:4,5-bis-0- isopropyliden-adonit 44 44 * 5-0-/f>-( 2-Chlor-4-trifluor- 4 4 4 4 methyl-phenoxy)-2-nitro--e benzoylj-1,2 : 3,4-bis-0- £( 4-chlorphenyl)-methylenj-xylitCompounds Viola / Matri- Viola / Matri- ._caria_caria_ 5-0- / 5- (2-chloro-4-trifluoromethÿl-phenoxy) -2-nitro-benzoyl / -1.2: 314-bis-0- 25 (isopröpyliden) -xylit 4 4 4 4 1-0- / 5- (2-chloro-4-trifluoromethÿl-phenoxy) -2-nitro-benzoyl7-2,3: 4,5-bis-0-isopropyliden- D-arabite 4 4 4 4 3-0- / 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoyl7-1.2: 4,5-bis-0-isopropylidene adonite 44 44 * 5-0- / f> - (2-chloro-4-trifluoro-4 4 4 4 methyl-phenoxy) -2-nitro - e benzoylj-1,2: 3,4-bis-0- £ ( 4-chlorophenyl) methylenej-xylitol
ï “/Lï “/ L
ψ· ^ Vorstand: Or. Herbert Asmis Dr. Christian Bruhn · Hans-Jürgen Hamann Postanschrift: SCHERING AG · D-1000 Berlin 65 · Postfach 650311 Z Dr. Heinz Hannse - Karl Otto Mittelstenseheid - Dr. Horst Witzei Postschedt-Konto : Berlin-West 1175-101. Bankleitzahl 10010010 J! Vorsitzender des Aufsichtsrats : Dr. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin, Konto-Nr. 1067006 00. Bankleitzahl 100 400 00 I Sitz der Gesellschaft : Berlin und Bergkamen Berliner Disconto-Bank AG. Berlin, Konto-Nr. 241/5006, BankloitzaN 100 700 00ψ · ^ Board: Or. Herbert Asmis Dr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AGD-1000 Berlin 65Postbox 650311 Z Dr. Heinz Hannse - Karl Otto Mittelstenseheid - Dr. Horst Witzei Postschedt account: Berlin-West 1175-101. Bank code 10010010 J! Chairman of the supervisory board: Dr. Edward v. Schwartzkoppen Berlin Commerzbank AG. Berlin, account no. 1067 006 00. Bank code 100 400 00 I Registered office of the company: Berlin and Bergkamen Berliner Disconto-Bank AG. Berlin, account no. 241/5006, BankloitzaN 100 700 00
SCHERING AGSCHERING AG
- IQ -- IQ -
Gewerblicher Rechtsschutz *Intellectual Property *
5 Erfindungsgemäße VORAUFLAUF NACHAUF LAUF5 PRE-RUN according to the invention AFTER-RUN
Verbindungen Viola/Matri- Viola/Watri- _________caria_caria 5-0- /5-(2-Chlor-4-trifluor- 4 4 4 4 methyl-phenoxy)-2-nitro-_ benzoylj - 1-, 2 : 3,4-bis-0- (chlormethyl-methylen)-xylit 5-0- [ß-(2-chlor-4-trifluor- 4 4 4 4 methyl-phenoxy)-2rrnitro-i benzoylj-1,2 : 3,4-bis-0- (methyl-octyl-methylen)-xylit 15 5-0- £5-(2-Chlor-4-trifluor- 4 4 4 4 methylphenoxy)-2-nitro-benzoylj-1,2 : 3 5 4-bis-0-(äthylmethylmethylen)-xylit 20 5-0-Γ5-(2-Chlor-4-trifluor- 4444 methylphenoxy)-2-nitro-benzoyl.7-1,2 : 314-bis-0-(diäthylmethylen)-xylit 5-0-^5-(2-Chlor-4-trifluor- 4444 25 methylphenoxy)-2-nitro- benzoylj^-1,2 : 3 * 4-bis-0-(methyImethylen)-xylit 30 * , 35 - 20 -Compounds Viola / Matri- Viola / Watri- _________caria_caria 5-0- / 5- (2-chloro-4-trifluoro-4 4 4 4 methyl-phenoxy) -2-nitro-_ benzoylj - 1-, 2: 3,4 -bis-0- (chloromethyl-methylene) -xylitol 5-0- [ß- (2-chloro-4-trifluoro-4 4 4 4 methyl-phenoxy) -2rrnitro-i benzoylj-1,2: 3,4- bis-0- (methyl-octylmethylene) xylitol 15 5-0- £ 5- (2-chloro-4-trifluoro-4 4 4 4 methylphenoxy) -2-nitro-benzoylj-1,2: 3 5 4 -bis-0- (ethylmethylmethylene) -xylitol 20 5-0-Γ5- (2-chloro-4-trifluoro-4444 methylphenoxy) -2-nitro-benzoyl.7-1.2: 314-bis-0- (diethylmethylene ) -xylitol 5-0- ^ 5- (2-chloro-4-trifluoro-4444 25 methylphenoxy) -2-nitro-benzoylj ^ -1.2: 3 * 4-bis-0- (methylene) -xylitol 30 * , 35 - 20 -
. /U. / U
§ '»r r- I j- Vorstand : Dr. Herbert Asmis · Dr. Christian Bruhn · Hans-Jürgen Hamann Postanschrift: SCHERING AG · 0-1 Berlin 65 · Postfach 650311 Π & n· Um2·« l/a.i nu_ iiiu.i.i..._j__r-a n. 11 1É f ! 1— _§ '»r r- I j- Board: Dr. Herbert AsmisDr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AG0-1 Berlin 65Pox PO Box 650311 Π & n · Um2 · «l / a.i nu_ iiiu.i.i ..._ j__r-a n. 11 1É f! 1- _
• · SCHERINGAG• · SCHERINGAG
- 20 Gewerblicher Rechtsschutz 4 5 BEISPIEL 11- 20 Intellectual Property Law 4 5 EXAMPLE 11
Im Gewächshaus wurden die aufgeführten Pflanzen nach dem > Auflaufen mit der auf geführten Verbindung in einer Aufwandmenge von 0,1 kg Wirkstoff/ha behandelt. Die Verbindung 10 wurde zu diesem Zweck als Emulsion mit 500 Litern Wasser/ha gleichmäßig über die Pflanzen versprüht. Hier zeigt 3 Wo-chen nach der Behandlung die erfindungsgemäße Verbindung eine hohe Selektivität bei ausgezeichneter Wirkung gegen „_ das Unkraut.In the greenhouse, the plants listed were treated after the> emergence with the compound listed at a rate of 0.1 kg of active ingredient / ha. For this purpose, compound 10 was sprayed evenly over the plants as an emulsion with 500 liters of water / ha. 3 weeks after the treatment, the compound according to the invention shows a high selectivity with excellent activity against the weeds.
15 20 as to15 20 as to
’ *H E <8 3 H’* H E <8 3 H
U 2 « Xi β £ ® » fi U -P -Η Ο V* •GO E 3 d «5 d « H d Q> <h c2 •Hfeoadaasoafc-H © +» o 3 u >ϊη·η-+> u «« « «+» d oe Erfxndungs gemäße ® ο·η* as a> E ft <u <a b οφφφ «s s*U 2 «Xi β £ ®» fi U -P -Η Ο V * • GO E 3 d «5 d« H d Q> <h c2 • Hfeoadaasoafc-H © + »o 3 u> ϊη · η - +> u «« «« + »the invention according to ® ο · η * as a> E ft <u <ab οφφφ« ss *
Verbindungen 5-0-/5-(2-Chlor- 4-trifluormethyl- phenoxy)-2-nitro- 0 0 0 0 0 0 o 0 00 1010 1010 1010 benzoyl/-1,2: 314-bis-O-Tisopropyl-^ iden)-xylit * »? 5-0-^5-(2-Chlor- 00 00 00 00 00 1010 1010 1010 4-trifluormethyl-phenoxy)-2-nitro-b enzoylj-1,2:3,4-35 bis-0-(methyl-octyl- methylen)-xylit 40.Compounds 5-0- / 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitro- 0 0 0 0 0 0 o 0 00 1010 1010 1010 benzoyl / -1.2: 314-bis-O-tisopropyl - ^ iden) -xylit * »? 5-0- ^ 5- (2-chloro- 00 00 00 00 00 1010 1010 1010 4-trifluoromethylphenoxy) -2-nitro-b enzoylj-1,2: 3,4-35 bis-0- (methyl- octyl methylene) xylitol 40.
I /— ~ Vorstand: Or. Herbert Asmis · Or. Christian Bruhn - Hans-Jürgen Hamann Postanschrift: SCHERING AQ · D-1000 Berlin es - Postfach 650311 4 Dr. Heinz Hannse · Karl Otto Mittelstenscheid - Dr. Horst Witzei Postscheck-Konto: Berlin-West 1175-101. Banklettzahl 10010010 • Vorsitzender des Aulsichtsrats: Or. Eduard v. Schwartzkoppen Berliner Commerzbank AG. Berlin. Konto-Nr. 100 7006 00. BankleitzahMOO 400 00 I Sitz der Gesellschaft : Berlin und Bergkamen Berliner Diseonto-Bank AG. Berlin, Konto-flr. 241/5000, BanklettzaM 100 700 00 £ 1/1 /-*« m ·mn mmm .. 4M t/ mn mm RftflinftT _ ΡίβηΗΐΐΠΒΤ fUfllf _ AirllnI / - ~ Board of Directors: Or. Herbert Asmis · Or. Christian Bruhn - Hans-Jürgen Hamann Postal address: SCHERING AQ · D-1000 Berlin es - Postfach 650311 4 Dr. Heinz HannseKarl Otto Mittelstenscheid - Dr. Horst Witzei postal check account: Berlin-West 1175-101. Number of banquets 10010010 • Chairman of the Supervisory Board: Or. Eduard v. Schwartzkoppen Berlin Commerzbank AG. Berlin. Account number. 100 7006 00. Bank sorting MOO 400 00 I Registered office: Berlin and Bergkamen Berliner Diseonto-Bank AG. Berlin, account flr. 241/5000, BanklettzaM 100 700 00 £ 1/1 / - * «m · mn mmm .. 4M t / mn mm RftflinftT _ ΡίβηΗΐΐΠΒΤ fUfllf _ Airlln
Claims (2)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823241830 DE3241830A1 (en) | 1982-11-09 | 1982-11-09 | 2-PHENOXYBENZOESAEUR DERIVATIVES OF PENTITES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND THIS CONTAINING AGENT WITH HERBICIDAL ACTION |
| DE3241830 | 1982-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU85080A1 true LU85080A1 (en) | 1984-04-02 |
Family
ID=6177935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU85080A LU85080A1 (en) | 1982-11-09 | 1983-11-09 | 5-PHENOXYBENZOESAEUR DERIVATIVES OF PENTITES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND THIS CONTAINING AGENT WITH HERBICIDAL ACTION |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5988480A (en) |
| KR (1) | KR840007582A (en) |
| AU (1) | AU2099083A (en) |
| BE (1) | BE898192A (en) |
| BR (1) | BR8305984A (en) |
| CS (1) | CS238397B2 (en) |
| DD (1) | DD210197A5 (en) |
| DE (1) | DE3241830A1 (en) |
| DK (1) | DK491383A (en) |
| ES (1) | ES526448A0 (en) |
| FI (1) | FI833883A7 (en) |
| FR (1) | FR2535719A1 (en) |
| GB (1) | GB2130581A (en) |
| GR (1) | GR79390B (en) |
| IL (1) | IL70161A0 (en) |
| IT (1) | IT1169899B (en) |
| LU (1) | LU85080A1 (en) |
| MA (1) | MA19950A1 (en) |
| NL (1) | NL8303084A (en) |
| NO (1) | NO834078L (en) |
| PT (1) | PT77577B (en) |
| SE (1) | SE8306046L (en) |
| TR (1) | TR21890A (en) |
| ZA (1) | ZA838360B (en) |
| ZW (1) | ZW24383A1 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2617804C2 (en) * | 1976-04-23 | 1985-01-24 | Hoechst Ag, 6230 Frankfurt | 2- (4-Phenoxy phenoxy) propionic acid derivatives and their use as herbicides |
-
1982
- 1982-11-09 DE DE19823241830 patent/DE3241830A1/en not_active Withdrawn
- 1982-11-09 ZA ZA838360A patent/ZA838360B/en unknown
-
1983
- 1983-09-05 NL NL8303084A patent/NL8303084A/en not_active Application Discontinuation
- 1983-09-21 JP JP58173271A patent/JPS5988480A/en active Pending
- 1983-10-13 ES ES526448A patent/ES526448A0/en active Granted
- 1983-10-24 FI FI833883A patent/FI833883A7/en not_active Application Discontinuation
- 1983-10-26 DK DK491383A patent/DK491383A/en not_active Application Discontinuation
- 1983-10-26 IT IT23446/83A patent/IT1169899B/en active
- 1983-10-28 PT PT77577A patent/PT77577B/en unknown
- 1983-10-31 BR BR8305984A patent/BR8305984A/en unknown
- 1983-11-03 SE SE8306046A patent/SE8306046L/en not_active Application Discontinuation
- 1983-11-04 AU AU20990/83A patent/AU2099083A/en not_active Abandoned
- 1983-11-07 DD DD83256409A patent/DD210197A5/en unknown
- 1983-11-07 TR TR21890A patent/TR21890A/en unknown
- 1983-11-07 GR GR72909A patent/GR79390B/el unknown
- 1983-11-08 IL IL70161A patent/IL70161A0/en unknown
- 1983-11-08 MA MA20170A patent/MA19950A1/en unknown
- 1983-11-08 GB GB08329750A patent/GB2130581A/en not_active Withdrawn
- 1983-11-08 NO NO834078A patent/NO834078L/en unknown
- 1983-11-09 ZW ZW243/83A patent/ZW24383A1/en unknown
- 1983-11-09 KR KR1019830005315A patent/KR840007582A/en not_active Withdrawn
- 1983-11-09 BE BE0/211848A patent/BE898192A/en not_active IP Right Cessation
- 1983-11-09 CS CS838272A patent/CS238397B2/en unknown
- 1983-11-09 FR FR8317796A patent/FR2535719A1/en not_active Withdrawn
- 1983-11-09 LU LU85080A patent/LU85080A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT8323446A0 (en) | 1983-10-26 |
| NL8303084A (en) | 1984-06-01 |
| MA19950A1 (en) | 1984-07-01 |
| IL70161A0 (en) | 1984-02-29 |
| ZW24383A1 (en) | 1984-05-02 |
| KR840007582A (en) | 1984-12-08 |
| FI833883A0 (en) | 1983-10-24 |
| ZA838360B (en) | 1984-07-25 |
| DK491383D0 (en) | 1983-10-26 |
| PT77577B (en) | 1986-03-18 |
| IT8323446A1 (en) | 1985-04-26 |
| ES8405388A1 (en) | 1984-06-16 |
| AU2099083A (en) | 1984-05-17 |
| DK491383A (en) | 1984-05-10 |
| ES526448A0 (en) | 1984-06-16 |
| PT77577A (en) | 1983-11-01 |
| SE8306046D0 (en) | 1983-11-03 |
| NO834078L (en) | 1984-05-10 |
| IT1169899B (en) | 1987-06-03 |
| GB8329750D0 (en) | 1983-12-14 |
| DD210197A5 (en) | 1984-06-06 |
| SE8306046L (en) | 1984-05-10 |
| GR79390B (en) | 1984-10-22 |
| GB2130581A (en) | 1984-06-06 |
| BR8305984A (en) | 1984-07-10 |
| BE898192A (en) | 1984-05-09 |
| CS827283A2 (en) | 1984-12-14 |
| DE3241830A1 (en) | 1984-05-10 |
| CS238397B2 (en) | 1985-11-13 |
| FI833883A7 (en) | 1984-05-10 |
| FR2535719A1 (en) | 1984-05-11 |
| JPS5988480A (en) | 1984-05-22 |
| TR21890A (en) | 1985-10-07 |
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