DE1919851A1 - N-3 5-dichlorophenyl-itaconimide - Google Patents

N-3 5-dichlorophenyl-itaconimide

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Publication number
DE1919851A1
DE1919851A1 DE19691919851 DE1919851A DE1919851A1 DE 1919851 A1 DE1919851 A1 DE 1919851A1 DE 19691919851 DE19691919851 DE 19691919851 DE 1919851 A DE1919851 A DE 1919851A DE 1919851 A1 DE1919851 A1 DE 1919851A1
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Germany
Prior art keywords
itaconimide
dichlorophenyl
nitrophenyl
chlorophenyl
methylphenyl
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DE19691919851
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German (de)
Inventor
Akira Fujinami
Fukashi Horiuchi
Katsuji Nodera
Tadashi Ooishi
Toshiaki Ozaki
Sigeo Yamaoto
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to DE19691919851 priority Critical patent/DE1919851A1/en
Priority to NL6906329A priority patent/NL144602B/en
Publication of DE1919851A1 publication Critical patent/DE1919851A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

N-(3,5-Dichlorophenyl)-itaconimide (I). Highly active antimicrobial agent, esp. as fungicide active against Piricularia oryzae, Chchliobolus miyabeanus, Pellicularia sasakii, Sclerotinia, Aspergillus niger, Non-toxic to agricultural and horticultural plants. By dehydration of N-(3,5-dichlorophenyl)-itaconic monoamide e.g. with acetic anhydride, PCl5, POCl3 etc.

Description

"N-(3',5'-Dichlorphenyl)-itaconimid, Verfahren zu seiner Herstellung und seine Verwendung als Microbicid oder in microbiciden Mitteln" Aus Chemical Abstracts, Bd. 57, Seite 14 947, Bd. 58, Seite 888 sowie Seite 4431 sind miorobicide N-Phenylitaconimide bekannt, nämlich N-Phenylitaconimid, N-(2'-Chlorphenyl)-itaconimid, N-(3'-Chlorphenyl)-itaconimid, N-(4'-Chlorphenyl)-itaconimid, N-(2'-Nitrophenyl)-itaconimid, N-(3'-Nitrophenyl)-itaconimid, N-(4'-Nitrophenyl)-itaconimid, N-(3'-Methylphenyl)-itaconimid, N-(4'-Methylphenyl)-itaconimid, N-(2'-Methoxyphenyl)-itaconimid, N-(4'-Methoxyphenyl)-itaconimid, N-(2',5'-Dimethylphenyl)-itaconimid, N-(2',6'-Dimethylphenyl)-itaoonimid, N-(2',5'-Dichlorphenyl)-itaconimid und N-(2'-Nitro-4'-methylphenyl)-itaconimid."N- (3 ', 5'-dichlorophenyl) itaconimide, process for its preparation and its use as a microbicide or in microbicidal agents "From Chemical Abstracts, Vol. 57, page 14 947, vol. 58, page 888 and page 4431 are miorobicide N-phenylitaconimides known, namely N-phenylitaconimide, N- (2'-chlorophenyl) -itaconimide, N- (3'-chlorophenyl) -itaconimide, N- (4'-chlorophenyl) -itaconimide, N- (2'-nitrophenyl) -itaconimide, N- (3'-nitrophenyl) -itaconimide, N- (4'-nitrophenyl) -itaconimide, N- (3'-methylphenyl) -itaconimide, N- (4'-methylphenyl) -itaconimide, N- (2'-methoxyphenyl) -itaconimide, N- (4'-methoxyphenyl) -itaconimide, N- (2 ', 5'-dimethylphenyl) -itaconimide, N- (2 ', 6'-dimethylphenyl) -itaoonimide, N- (2', 5'-dichlorophenyl) -itaconimide and N- (2'-nitro-4'-methylphenyl) -itaconimide.

Aufgabe der Erfindung ist es, ein neues N-Phenylitaoonimid-Derivat zur Verfügung zu stellen, dass eine wesentlich höhere microbicide Aktivität aufweist, als die bekannten Verbindungen. Somit betrifft die Erfindung das neue N-(3',5'-Dichlorphenyl)-itaconimid sowie ein Verfahren zu seiner Herstellung0 Das Verfahren ist dadurch gekennzeichnet, dass man N-(3',5'-Dichlorphenyl)-itaconsäuremonoamid dehydratisiert0 In der Praxis wird das Verfahren der Erfindung so durchefuhrt dass man das Itaconsäuremonoamid mit einem geeigneten Dehydratisierungsmittel, wie essigsäureanhydrid Acetylchlorids Phosphorpentachlorid oder Phosphoroxy chlorids vorzugsweise Essigsäureanhydrid, unter Rückfluss kocht und rührt. Im allgemeinen genügt ein l-stündiges Kochen unter Rückfluss EB wurde festgestellt, dass das erfindungsgemäss hergestellte N-(3',5'-Dichlorphenyl)-itaconimid eine besonders hohe microbi cide Wirkung gegenüber den verschiedensten pflanzenpathogenen Bakterien und Pilzen zeigt Besonders wirksam ist die Verbindung gegenüber Piricularia oryzae, Cochliobolus miyabeanus, Pellicularia sasakii, Sclerotinia und Aspergillus niger, Die erfindungsgemäss herstellbare Verbindung kann als solche oder zusammen mit anderen Bestandteilen, wie inerten Trägerstoffen, verwendet werden.The object of the invention is to provide a new N-phenylitaoonimide derivative to make available that has a significantly higher microbicidal activity, than the known compounds. Consequently the invention relates to the new N- (3 ', 5'-dichlorophenyl) -itaconimide and a process for its preparation0 The process is characterized in that N- (3 ', 5'-dichlorophenyl) -itaconic acid monoamide dehydrated0 In practice the method of the invention is carried out such that the itaconic acid monoamide with a suitable dehydrating agent such as acetic anhydride Acetyl chloride phosphorus pentachloride or phosphorus oxychloride preferably acetic anhydride, boils under reflux and stirs. In general, boiling for 1 hour is sufficient Reflux EB was found that the N- (3 ', 5'-dichlorophenyl) itaconimide prepared according to the invention a particularly high microbiocide effect against a wide variety of phytopathogens Bacteria and fungi shows the compound is particularly effective against Piricularia oryzae, Cochliobolus miyabeanus, Pellicularia sasakii, Sclerotinia and Aspergillus niger, The compound which can be produced according to the invention can be used as such or together can be used with other ingredients such as inert carriers.

Zur Herstellung von fungiciden Mitteln wird das N-(3',5'-Dichlorphenyl)itaconimid æOBO als Stäubemittel, benetzbares Pulver, emulgierbares Konzentrat oder als Granulat verarbeitet. Den fungiciden Mitteln können zoBJ noch Antibiotica, andere Pesticide, wie Hexachlorcyclohexan, Organophosphorverbindungen, organische Arsenverbindungen, organische Sulfide und Carbamate 9 Blasticidin S, Kasugamycin, O,O-Piäthyl-S-benzylthiophosphorsäureester, O-Äthyl-8,8-diphenyldithiophosphorsäureester, Pentachlorbenzaldoxim, O-Butyl-S-benzyl-S-äthyldithiophosphat, Eisenmethylarsonat, Zineb, Maneb, N-(3,5-Dichlorphenyl)-meleinimid, N-(3,5-Dichlorphenyl)-succinimid, O-Äthyl-O-phenyl-O-(2,4,5-trichlorphenyl)-phosphat, 1-(N-n-Butylcarbamoyl)-2-methoxycarbonylaminobenzimidazol, Malathion, Dimethoate, EPN, NAC, Meobal oder Sumithion einverleibt werden0 Ferner können die fungiciden Mittel auch zusammen mit anderen landwirtschaftlichen Chemikalien, wie Herbiciden, Nematociden, Miticiden oder Düngemitteln verwendet werden Die Beispiele erläutern die Erfindung. Teile beziehen sich auf das Gewicht, sofern nichts anderes angegeben ist, Beispiel l 27,4 g N-(3',5'-Dichlorphenyl)-itaconsäuremonoamid, 50 g Easigsäureanhydrid und 1 g Natriumacetat werden in einen 100 ml fassenden Vierhalskolben gegeben und eine Stunde unter Rückfluss ge kocht und gerührt, Danach werden Essigsäure und Essigsäureanhydrid unter verminuertem Druck abdestilliert9 der Rückstand wird mit WaEser gewaschen und getrocknet. Das Rohprodukt wird aus Alkohol umkristallisiert. Ausbeute 21,5 g weisse Kristalle von Fo 142 bis 1430 Cc C H N Cl ber.: 51,59; 2,76; 5,47; 27,69; gef.: 51,53 2,63; 5,35; 27,87.N- (3 ', 5'-dichlorophenyl) itaconimide is used to produce fungicidal agents æOBO as a dusting agent, wettable powder, emulsifiable concentrate or as granules processed. In addition to fungicides, antibiotics, other pesticides, such as hexachlorocyclohexane, organophosphorus compounds, organic arsenic compounds, organic sulfides and carbamates 9 blasticidin S, kasugamycin, O, O-ethyl-S-benzylthiophosphoric acid ester, O-ethyl-8,8-diphenyldithiophosphoric acid ester, pentachlorobenzaldoxime, O-butyl-S-benzyl-S-ethyldithiophosphate, Iron methyl arsonate, Zineb, Maneb, N- (3,5-dichlorophenyl) -meleinimide, N- (3,5-dichlorophenyl) -succinimide, O-ethyl-O-phenyl-O- (2,4,5-trichlorophenyl) -phosphate, 1- (N-n-butylcarbamoyl) -2-methoxycarbonylaminobenzimidazole, Malathion, Dimethoate, EPN, NAC, Meobal or Sumithion are also incorporated the fungicides can also be used together with other agricultural chemicals, such as herbicides, nematocides, miticides or fertilizers can be used. The examples explain the invention. Parts are by weight unless otherwise is given, Example 1 27.4 g of N- (3 ', 5'-dichlorophenyl) -itaconic acid monoamide, 50 g acetic anhydride and 1 g sodium acetate are placed in a 100 ml four-necked flask given and refluxed and stirred for one hour, then acetic acid and acetic anhydride is distilled off under reduced pressure9 the residue is washed with water and dried. The crude product is recrystallized from alcohol. Yield 21.5 g of white crystals of Fo 142 to 1430 Cc C H N Cl calc .: 51.59; 2.76; 5.47; 27.69; Found: 51.53 2.63; 5.35; 27.87.

Beispiel 2 3 Teile N-(3',5'-Dichlorphenyl)-itaconimid und 97 Teile Ton werden gründlich miteinander vermischt und pulverisiert0 Man erhält ein Stäubemittel nit 3 % wirkstoffgehalt. Dieses Stäubemittel kann als solches verwendet werden Beispiel 3 50 Teile N-(3',5'-Dichlorphenyl)-itaconimid, 5 Teile eines Netzmittels vom Alkylbenzolsulfonattyp und 45 Teile Diatomeenerde werden gründlich miteinander vermischt und pulverisiert. Man erhält ein benetzbares Pulver mit einem Wirkstoffgehalt von 50 *0 Zur Anwendung wird das benetzbare Pulver mit Wasser verdünnt und verspritzt0 Beispiel 4 5 Teile N-(3',5'-Dichlorphenyl)-itaconimid, 5 Teile eines Emulgators vom Polyoxäthylenalkylphenoläther-Typ und 90 Teile DimethyX-sulfoxyd werden miteinander vermischt, Man erhält ein 5 %-iges emulgierbares Konzentrat, das nach dem Verdünnen mit Wasser ver spritzt werden kann0 Beispiel 5 Reispflanzen der Sorte Wase Asahi, die in Blumentöpfen mit einem Durchmesser von-9 cm bis zum 3-blättrigen Stadium gezogen wurden9 werden einzeln mi.t den zu untersuchenden Stäubemitteln in einer Menge von 100 mg Je Blumentopf besprüht. Am nächsten Tag-werden die Reispflanzen mit den Sporen von Piricularia oryzae Cav. beimpftO 5 Tage nach der Beimpfung wird die Zahl der Krankheitsflecken bestimmt, Die Ergebnisse sind in Tabelle I zusammengestellt, Tabelle I r. Testverbindung Wirkstoff- Zahl der konzentra- Flecken pro tion, % 10 Blätter 1 N-(3'5'-Dichlorphenyl)-itaconimid 3,0 5 2 N-Phenylitaconimid 3,0 108 3 N-(2'-Chlorphenyl)-itaconimid 3,0 203 4 N-(3'-Chlorphenyl)-itaconimid 3,0 186 5 N=(42-Chlorphenyl)-itaconimid 3,C 191 6 N-(2'-Nitrophenyl)-itaconimid 3,0 226 7 N-(3'-Nitrophenyl)-itaconimid 3,0 237 8 N-(4'-Nitrophenyl)-itaconimid 3,0 211 9 N-(3'-Methylphenyl)-itaconimid 3.° 199 10 N-(4'-Methylphenyl)-itaconimid 3,0 214 11 N-(2'-Msthoxyphelyl)-itaconinid 3,0 356 12 N-(4'-Methoxyphenyl)-itaconimid 3,0 292 13 N-(2',5'-Dimethylphenyl)-itaconimid 3,0 237 14 N-(2',6'-Dimethylphenyl)-itaconimid 3,0 209 15 N-(2',5'-Dichlorphenyl)-itaconimid 3,0 105 16 N-(2'-Nitro-4'-methylphenyl)- 3,0 256 itac onimid 17 Phenylquecksilberacetat 0,29 18 18 unbehandelt - 382 Beispiel 6 Reispflanzen der Sorte Wase Asahi, die in Blumentöpfen mit einem Durchmesser von 9 cm bis zum 4-blättrigen Stadium gezogen wurden werden einzeln in einer Menge von 7 ml je Topf mit benetzbaren Pulvern besprüht, die mit Wasser verdünnt sind0 Am nächsten Tag werden die Reispflanzen mit den Sporen von Cochliobolus miyabeanus durch Sprühen beimpft. 4 Tage nach der Beimpfung wird die Zahl der Krankheitsflecken bestimmt. Die Ergebnisse sind in Tabelle II zusammengesetellt.Example 2 3 parts of N- (3 ', 5'-dichlorophenyl) itaconimide and 97 parts of clay are thoroughly mixed with one another and pulverized. A dust with a 3% active ingredient content is obtained. This dust can be used as it is. Example 3 50 parts of N- (3 ', 5'-dichlorophenyl) itaconimide, 5 parts of an alkylbenzenesulfonate type wetting agent and 45 parts of diatomaceous earth are thoroughly mixed together and pulverized. A wettable powder with an active ingredient content of 50 * is obtained. For use, the wettable powder is diluted with water and sprayed. Example 4 5 parts of N- (3 ', 5'-dichlorophenyl) itaconimide, 5 parts of an emulsifier of the polyoxyethylene alkylphenol ether type and 90 parts of DimethyX sulfoxide are mixed together. A 5% emulsifiable concentrate is obtained which, after dilution with water, can be sprayed on -leaf stage9 are sprayed individually with the dusts to be examined in an amount of 100 mg per flower pot. The next day-the rice plants with the spores of Piricularia oryzae Cav. inoculated. 5 days after inoculation, the number of disease spots is determined. The results are summarized in Table I, Table I. r. Test compound active ingredient number of concentra- stains per tion,% 10 sheets 1 N- (3'5'-dichlorophenyl) itaconimide 3.0 5 2 N-phenylitaconimide 3.0 108 3 N- (2'-chlorophenyl) itaconimide 3.0 203 4 N- (3'-chlorophenyl) itaconimide 3.0 186 5 N = (42-chlorophenyl) itaconimide 3, C 191 6 N- (2'-nitrophenyl) itaconimide 3.0 226 7 N- (3'-nitrophenyl) itaconimide 3.0 237 8 N- (4'-nitrophenyl) itaconimide 3.0 211 9 N- (3'-methylphenyl) itaconimide 3rd ° 199 10 N- (4'-methylphenyl) itaconimide 3.0 214 11 N- (2'-Msthoxyphelyl) -itaconinide 3.0 356 12 N- (4'-methoxyphenyl) itaconimide 3.0 292 13 N- (2 ', 5'-dimethylphenyl) itaconimide 3.0 237 14 N- (2 ', 6'-dimethylphenyl) itaconimide 3.0 209 15 N- (2 ', 5'-dichlorophenyl) itaconimide 3.0 105 16 N- (2'-nitro-4'-methylphenyl) - 3.0 256 itac onimid 17 phenyl mercury acetate 0.29 18 18 untreated - 382 Example 6 Rice plants of the Wase Asahi variety which have been grown in flower pots with a diameter of 9 cm to the 4-leaf stage are individually sprayed in an amount of 7 ml per pot with wettable powders which are diluted with water Rice plants inoculated with the spores of Cochliobolus miyabeanus by spraying. The number of disease spots is determined 4 days after inoculation. The results are summarized in Table II.

Tabelle II # Wirkstoff- Zahl der Nr. Testverbindung Wirkstoff- Zahl der konzentra- Flecken tion, TpM pro Blatt 1 N-(3',5'-Dichlorphenyl)-itaconimid 500 0 2 N-Phenylitaconimid 500 57 3 N-(2'-Chlorphenyl)-itaconimid 500 46 4 N-(3'-Chlorphenyl)-itaconimid 500 49 5 N-(4'-Chlorphenyl)-itaconimid 500 58 6 N-(2'-Nitrophenyl)-itaconimid 500 52 7 N-(3'-Nitrophenyl)-itaconimid 500 53 8 N-(4'-Nitrophenyl)-itaconimid 500 60 9 N-(3'-Methylphenyl)-itaconimid 500 45 10 N-(4'-Methylphenyl)-itaconimid 1 500 48 11 N-(2'-Methoxyphenyl)-itaconimid 500 63 12 N-(4'-Methoxyphenyl)-itaconimid 500 59 13 N-(2',5'-Dimethylphenyl)-itaconimid 500 41 14 N-(2',6'-Dimethylphenyl)-itaconimid 500 63 15 N-(2',5'-Dichlorphenyl)-itaconimid 500 52 16 N-(2'-Nitro-4'-methylphenyl)-itaconimid 500 61 17 unbehandelt # - 87 Beispiel 7 Reispflanzen der Sorte Wase Asahi, die in 300 ml fassenden Töpfen aus Polyvinylchlorid bis zu einer Höhe von etwa 60 cm gezogen wurden, werden einzeln in einer Menge von 10 ml Je Topf mit wässrigen Emulsionen besprüht. Am nächsten Tag werden die Blätter und Stengel der Reispflanzen mit Hycelteilchen mit einem Burchmesser von 5 mm von Pellicularia sasakii beimpft. 5 Tage nach der Beimpfung wird die Zahl der erkrankten Blätter und Stengel bestimmt. Die Ergebnisse sind in Tabelle III zusammengestellt0 Tabelle III Nr. Testverbindung Wirkstoff- Erkren konzentra- kung der tion, TpM Blätter und Sten- gel. % 1 N-(3',5'-Dichlorphenyl)-itaconimid 500 0 2 N-(Phenylitaconimid 500 88,4 3 N-(2'-Chlorphenyl)-itaconimid 500 100 4 N-(3'-Chlorphenyl)-itaconimid 500 100 5 N-(4'-Chlorphenyl)-itaconimid 500 100 6 N-(2'-Nitrophenyl)-itaconimid 500 100 7 N-(3'-Nitrophenyl)-itaconimid 500 100 8 N-(4'-Nitrophenyl)-itaconimid 500 100 9 N-(3'-Methylphenyl)-itaconimid 500 100 10 N-(4'-Methylphenylj-itaconixid 500 100 11 N-(2'-Methoxyphenyl)-itaconimid 500 100 12 N-(4'-Methoxyphenyl)-itaconimid 500 100 13 N-(2',5'-Dimethylphenyl)-itaconimid 500 97,6 14 N-(2',6'-Dimethylphenyl)-itaconimid 500 93,4 15 N-(2',5'-Dichlorphenyl)-itaconimid 500 89,1 16 N-(2'-Nitro-4'-methylphenyl)-itaconimid 500 100 17 unbehandelt - 100 Beispiel 8 Nach der Verdünnungsmethode wird die Mindesthemmkonzentration von N-(3',5'-Dichlorphenyl)-itaconimid gegenüber den verschiedensten Mikroorganismen bestimmt. Eine Lösung von N-(3',5'-Dichlorphenyl) -itaconimid in Dioxan wird mit einem warmen, sterilisierten Kartoffelagermedium in einer Menge von 1 ml der Lösung Je 10 ml den Aßarmediums vermischt. Daß Gemisch wird in Petriachalen gegossen und erstarren gelassen. Danach wird jede Petrischale mit einer Suspension dss Nilcroorganismus beimpft. Die Konzentration der Testverbindung im Agarmedium beträgt 1000, 200, 40 und 8 TpM.Table II # Active ingredient number of No test compound active ingredient number of concen- tral spots tion, TPM per sheet 1 N- (3 ', 5'-dichlorophenyl) itaconimide 500 0 2 N-phenylitaconimide 500 57 3 N- (2'-chlorophenyl) itaconimide 500 46 4 N- (3'-chlorophenyl) itaconimide 500 49 5 N- (4'-chlorophenyl) itaconimide 500 58 6 N- (2'-nitrophenyl) itaconimide 500 52 7 N- (3'-nitrophenyl) itaconimide 500 53 8 N- (4'-nitrophenyl) itaconimide 500 60 9 N- (3'-methylphenyl) itaconimide 500 45 10 N- (4'-methylphenyl) itaconimide 1,500 48 11 N- (2'-methoxyphenyl) itaconimide 500 63 12 N- (4'-methoxyphenyl) itaconimide 500 59 13 N- (2 ', 5'-dimethylphenyl) itaconimide 500 41 14 N- (2 ', 6'-dimethylphenyl) itaconimide 500 63 15 N- (2 ', 5'-dichlorophenyl) itaconimide 500 52 16 N- (2'-nitro-4'-methylphenyl) itaconimide 500 61 17 untreated # - 87 Example 7 Rice plants of the Wase Asahi variety, which were grown in 300 ml pots made of polyvinyl chloride to a height of about 60 cm, are sprayed individually in an amount of 10 ml per pot with aqueous emulsions. The next day, the leaves and stems of the rice plants are inoculated with Hycel particles with a diameter of 5 mm from Pellicularia sasakii. The number of diseased leaves and stems is determined 5 days after inoculation. The results are shown in Table III. Table III No. test compound active ingredient recognition concentration of tion, TpM sheets and star gel.% 1 N- (3 ', 5'-dichlorophenyl) itaconimide 500 0 2 N- (phenylitaconimide 500 88.4 3 N- (2'-chlorophenyl) itaconimide 500 100 4 N- (3'-chlorophenyl) itaconimide 500 100 5 N- (4'-chlorophenyl) itaconimide 500 100 6 N- (2'-nitrophenyl) itaconimide 500 100 7 N- (3'-nitrophenyl) itaconimide 500 100 8 N- (4'-nitrophenyl) itaconimide 500 100 9 N- (3'-methylphenyl) itaconimide 500 100 10 N- (4'-methylphenylj-itaconixide 500 100 11 N- (2'-methoxyphenyl) itaconimide 500 100 12 N- (4'-methoxyphenyl) itaconimide 500 100 13 N- (2 ', 5'-dimethylphenyl) itaconimide 500 97.6 14 N- (2 ', 6'-dimethylphenyl) itaconimide 500 93.4 15 N- (2 ', 5'-dichlorophenyl) itaconimide 500 89.1 16 N- (2'-nitro-4'-methylphenyl) itaconimide 500 100 17 untreated - 100 Example 8 The minimum inhibitory concentration of N- (3 ', 5'-dichlorophenyl) itaconimide against a wide variety of microorganisms is determined by the dilution method. A solution of N- (3 ', 5'-dichlorophenyl) -itaconimide in dioxane is mixed with a warm, sterilized potato storage medium in an amount of 1 ml of the solution per 10 ml of the assar medium. The mixture is poured into petri dishes and allowed to solidify. Each Petri dish is then inoculated with a suspension of the Nile croorganism. The concentration of test compound in the agar medium is 1000, 200, 40 and 8 ppm.

Die 5 Tage nach der Beimpfung erhaltenen Ergebnisse sind in Ta belle IV zusammengestellt.The results obtained 5 days after inoculation are in the table IV compiled.

Tabelle IV Testorganismus Mindesthemmkonzentration, TpM Piiicuiaria oryzae # 40 Cochliobelus miyabeanus 8 Alternaria kikuchiana 8 Alternaria ali 1 8 Pythium aphanidermatum 1 200 Pellicularia sasakii 200 Pellicularia filamentosa 8 Helminthosporium sigmoidium 40 Fusarium oxysporum f. niveum 200 Corticium rolfsi.i 1 200 Betrytis cinerea 8 Gloumerella cingulata 8 Xanthomonas oryzae 40 Aspergillus niger 40 Solerotinia solerotiorum 8 Aus den Tabellen ist ersichtlich, dass die microbicide Aktivität von N-(3',5'-Dichlorphenyl)-itaconimid gegenüber den verschiedensten Mikroorganismen wesentlich höher ist als die der chemisch und strukturell verwandten Verbindungen, Somit kann diese. Verbindung zur Bekämpfung von Pflanzenkrankheiten verwendet werden, die durch pflanzenpathogene Pilse und andere Krankheitserreger erzeugt werdenr zoBo den Erreger der Brusone-Krankheit, Ophiobolus miyabeanus, Corticium sasakii, Baumwollbakteriose, Mehltau bei Gemüssen und Früchten, Grauschimmel der Erdbeeren, Anthracnose und Pfirsichschorf. Ferner können sie zur Bekämpfung von Aspergillus niger verwendet werdenTable IV Test organism minimum inhibitory concentration, TpM Piiicuiaria oryzae # 40 Cochliobelus miyabeanus 8 Alternaria kikuchiana 8 Alternaria ali 1 8 Pythium aphanidermatum 1 200 Pellicularia sasakii 200 Pellicularia filamentosa 8 Helminthosporium sigmoidium 40 Fusarium oxysporum f. Niveum 200 Corticium rolfsi.i 1 200 Betrytis cinerea 8 Gloumerella cingulata 8 Xanthomonas oryzae 40 Aspergillus niger 40 Solerotinia solerotiorum 8 From the tables it can be seen that the microbicidal activity of N- (3 ', 5'-dichlorophenyl) -itaconimide against a wide variety of microorganisms is significantly higher than that of the chemically and structurally related compounds. Compound can be used to combat plant diseases caused by phytopathogenic fungi and other pathogens r zoBo the causative agent of Brusone's disease, Ophiobolus miyabeanus, Corticium sasakii, cotton bacteriosis, powdery mildew in vegetables and fruits, gray mold of strawberries, anthracnose and peach scab. They can also be used to control Aspergillus niger

Claims (1)

P a t e n t a n s p r ü c h e lo N-(3' 5 ' -Dichlórphenyl)-itaoonimidO 2o Verfahren zur Herstellung von N-(3',5'-Dichlorphenyl)-itaconimid nach Anspruch 1, d a d u r c h g e k e n n -z e i c h n e t, dass man N-(3',5'-Dichlorphenyl)-itaconsäuremonoamid dehydratisiert. P a t e n t a n s p r ü c h e lo N- (3 '5' -Dichlórphenyl) -itaoonimidO 2o process for the preparation of N- (3 ', 5'-dichlorophenyl) -itaconimide according to claim 1, d u r c h e k e n n -z e i c h n e t that one is N- (3 ', 5'-dichlorophenyl) -itaconic acid monoamide dehydrated. 3. Verwendung von N-(3',5'-Dichlorphenyl)-itaconimid als Microbicid oder in microbiciden Mitteln.3. Use of N- (3 ', 5'-dichlorophenyl) -itaconimide as a microbicide or in microbicidal agents.
DE19691919851 1969-04-18 1969-04-18 N-3 5-dichlorophenyl-itaconimide Withdrawn DE1919851A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE19691919851 DE1919851A1 (en) 1969-04-18 1969-04-18 N-3 5-dichlorophenyl-itaconimide
NL6906329A NL144602B (en) 1969-04-18 1969-04-24 PROCESS FOR PREPARING A MICROBIOCIDE ACTIVE N- (DICHLOROPHENYL) ITACONIMIDE AND MICROBICIDE COMPOSITIONS FORMED THEREOF.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691919851 DE1919851A1 (en) 1969-04-18 1969-04-18 N-3 5-dichlorophenyl-itaconimide

Publications (1)

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DE1919851A1 true DE1919851A1 (en) 1970-10-29

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DE19691919851 Withdrawn DE1919851A1 (en) 1969-04-18 1969-04-18 N-3 5-dichlorophenyl-itaconimide

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DE (1) DE1919851A1 (en)
NL (1) NL144602B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0190755A2 (en) * 1985-02-07 1986-08-13 Asahi Kasei Kogyo Kabushiki Kaisha An n-substituted-phenylteraconimide compound, herbicidal composition, and method for the destruction of undesirable weeds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0190755A2 (en) * 1985-02-07 1986-08-13 Asahi Kasei Kogyo Kabushiki Kaisha An n-substituted-phenylteraconimide compound, herbicidal composition, and method for the destruction of undesirable weeds
EP0190755A3 (en) * 1985-02-07 1988-05-04 Asahi Kasei Kogyo Kabushiki Kaisha An n-substituted-phenylteraconimide compound, herbicidal composition, and method for the destruction of undesirable weeds
US4964905A (en) * 1985-02-07 1990-10-23 Asahi Kasei Kogyo Kabushiki Kaisha N-substituted-phenylteraconimide compound, herbicidal composition, and method for the destruction of undesirable weeds

Also Published As

Publication number Publication date
NL144602B (en) 1975-01-15
NL6906329A (en) 1970-10-27

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