DE2133056A1 - Fungicidal guanidines - for combatting mildew and grey mould - Google Patents

Fungicidal guanidines - for combatting mildew and grey mould

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DE2133056A1
DE2133056A1 DE19712133056 DE2133056A DE2133056A1 DE 2133056 A1 DE2133056 A1 DE 2133056A1 DE 19712133056 DE19712133056 DE 19712133056 DE 2133056 A DE2133056 A DE 2133056A DE 2133056 A1 DE2133056 A1 DE 2133056A1
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dimethyl
methyl
chlorophenylguanidine
phenylguanidine
fungicidal agents
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DE2133056C3 (en
DE2133056B2 (en
Inventor
Sergej F Besuglij
Geb Cebrikowa Ljubow N Chanina
Nikolaj M Golyschin
Leonid A Kiselew
Nikow Nikolaj N Mel
Wera S Nabatowa
Michail R Obzischtscher
Boris A Saikin
Michail A Sanin
Geb Knj Schwezowa-Schulowskaja
Geb Romanytschewa Lju Sinowewa
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VNII KHIM SREDSTW SASCHTSCHITY
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VNII KHIM SREDSTW SASCHTSCHITY
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings

Abstract

Fungicidal agent for combatting mildew fungi and grey moulds on plants contains as active substance a cpd of formula (I) (where R is H, Me, Et, n-Pr or i-Pr; R1 is Me, Et, n-Pr, i-Pr, n-Bu, i-Bu or pentyl; and X, Y and Z are H, Cl, Br, Me, OMe, NO2 or CF3) or a salt thereof of the formula (I). HB (in which B is Cl', CH3SO4'.(CH3)2NCSS', S4O6"6, or C6H2(NO2)3O'). The cpds have the advantages of being obtainable relatively cheaply from readily accessible starting materials. Test results given in the specification show that (I) have good activity against mildew fungi on cucumbers and apples and Botrytis fabae on beans.

Description

MITTEL FUNGIZIDE AUF DER BASIS VON N,N-DI-(BZW.-MONO)-ALKYL-N'-ARYLSUBSTITUIERTEN GUANIDINEN ZUR BEKÄMPFUNG VON MEHLTAUPILZEN UND GRAUSCHIMMEL DER PFLANZEN Die vorliegende erfindung betrifft fungizide Präparate auf der Basis von N,N-di-(bzw.-mono)-alkyl-N'-arylsubstituierten Guanidinen zur Bekämpfung von Mehltaupilzen (Erysiphacae) und Grauschimmel (Botrytis) der Planzen.AGENTS FUNGICIDES BASED ON N, N-DI (OR MONO) -ALKYL-N'-ARYL SUBSTITUTES GUANIDINES FOR CONTROL OF MEAL FUNGI AND GRAY MOLD OF PLANTS The present The invention relates to fungicidal preparations based on N, N-di (or mono) -alkyl-N'-aryl-substituted Guanidines to combat powdery mildew (Erysiphacae) and gray mold (Botrytis) of the plants.

Es ist bekannt, daß zur Bekämpfung von Mehltaupilzen anorganische Schwefelpräparate weitgehend verwendet werden. Die Schwefelpräparate, die über eine hohe Wirksamkeit gegenüber Mehtaupilzen verfügen, haben jedoch auch negative Eigenschaften. Diese Präparate können die Pflanzen schädien, sind nicht genügend wirksam bei einer Lufttemperatur unter 200C und haben eine schwache ausrottende Wirkung. It is known that inorganic mildew fungi are used to combat powdery mildew Sulfur supplements are widely used. The sulfur supplements that have a have high effectiveness against Mehtauppilzen, but also have negative Properties. These preparations can harm the plants, but are not effective enough for one Air temperature below 200C and have a weak eradicating effect.

Das "Karathan" (2,4-Dinitro-6-sek-oktylphenylkrotonat)Handelsprodukt (der Firma Bohm und Haas , USA ,hat eine weitgehende Verwendung bei der Bedampfung von Mehltaupilzen in der Landwirtschaft gefunden. Bei Verwendung von "Karathan" in Konzentrationen von 0,025 - 0,05% des Wirkstoffes werden jedoch Brandwunden der Pflanzenblätter beobachtet. The "Karathan" (2,4-dinitro-6-sec-octylphenyl crotonate) commercial product (from Bohm and Haas, USA, is widely used in steaming of powdery mildew fungi found in agriculture. When using "Karathan" in concentrations of 0.025-0.05% of the active ingredient, however, burn wounds are the Plant leaves observed.

Zur Bekämpfung von Mehltaupilzen erwies sich als sehr wirksam das "Morestan" (6-Methylchinoxalin-2,3-dithiol-Handelsprödukt karbonat), der Firma Bayer (vgl. F. Grewe/ H. Kaspers, "Pflanzenschutz-Nachr. Bayer", Bd. 18, Seite 1-23, 1965). This proved to be very effective in combating powdery mildew "Morestan" (6-methylquinoxaline-2,3-dithiol commercial product carbonate), from Bayer (cf. F. Grewe / H. Kaspers, "Pflanzenschutz-Nachr. Bayer", Vol. 18, Pages 1-23, 1965).

Es muß jedoch betont werden, daß das "Morestan" eine geringe Wirksamkeit gegenüber Erregern anderer Krankheiten und insbesondere gegen den Grauschimmel an Pilzen aufweist, Es ist bekannt die Verwendung des Präparats "Euparen" T,N-Dimethyl-N' phenyl-6N'-£luordichlormethylJ-thiosul-Handelsprodukt famid), der Firma Bayer, zur Bekämpfung von Krankheiten, erregt durch die Pilze Botrytis sp.( Pflanzenschutzachr. Bayer", Bd. 21, S. 147, 257, 1968). M. Bonnet D. Hortic. Sci., Bd. 44, S. 81, 1969) berichtet über die hemmende Wirkung des Präparats "Europaren" bezüglich Sphaarotheca achemillae. Bekannt ist auch die Verwendung von "Capt- Handelsprodukt (N-Trichlormethylmercapto-4-zyklohexan-1,2-dikarboximid) der Firm Stauffer und Calif. Chem., USA, und von "Difelatan" (N-1,1,2,2-Tetrachloräthylmercapto-4-zyklo-Handelsprodukt hexen-1,2-dikarboximid), der Firma "Calif. Chem.", USA, zur Bekämpfung der pilzlichen Pflanzenschädlinge Botrytis sp. However, it must be emphasized that the "Morestan" has a low effectiveness against pathogens of other diseases and especially against gray mold It is known to use the preparation "Euparen" T, N-Dimethyl-N ' phenyl-6N'- £ luordichloromethylJ-thiosul commercial product famid), the company Bayer, for Combating diseases caused by the fungi Botrytis sp. Bayer ", Vol. 21, p. 147, 257, 1968). M. Bonnet D. Hortic. Sci., Vol. 44, p. 81, 1969) reports on the inhibiting effect of the preparation "Europaren" on Sphaarotheca achemillae. The use of "Capt- Commercial product (N-trichloromethylmercapto-4-cyclohexane-1,2-dicarboximide) from Stauffer and Calif. Chem., USA, and from "Difelatan" (N-1,1,2,2-tetrachloroethylmercapto-4-cyclo-commercial product hexen-1,2-dicarboximide), from "Calif. Chem.", USA, for combating fungal Plant pests Botrytis sp.

(F. Stellwaag-Kintler, Weinberg und Keller, Bd. 16, S. 109, 1969; G. Etter, "Meded. Rijksfac. landboutwwetensch. Gent", n. 31, S. 837, 1966).(F. Stellwaag-Kintler, Weinberg and Keller, Vol. 16, p. 109, 1969; G. Etter, "Meded. Rijksfac. Landboutwwetensch. Gent", n.31, p. 837, 1966).

und Die Präparate "Euparen, "Captan "Difolatan" besitzen je-«och keine bzw. eine schwache Aktivität bezüglich auf die s..ehltaupilze.and The preparations "Euparen," Captan, "Difolatan" do not have any or weak activity in relation to the mildew fungi.

Bekannt sind Fungizide auf der Basis von N-Arylguanidinderivaten, die eine hohe bakterizide, herbizide, insektizide und fungizide Aktivität besitzen, der allgemeinen Bormel rin wog ar ein mono- bzw. pol zyklischer aromatischer Rest ist, und der verschiedene Substituenten enthält, und R, R' # R" gleiche bzw. verschiedene niedrige aliphatische Reste sind, wobei einer von ihnen eine niedrige Alkoxygruppe sein kann (französische Patentschrift Nr. 1.541.647). Die erwähnten Verbindungen werden jedoch mit Hilfe komplizierterer und tougrer Verfahren hergestellt, als die nachstehend vorgeschlagenen. 1 Ziel der vorliegenden Erfindung ist neue Fungizide auf der Basis von N,N-di-(bzw. mono)alkyl-N'-arylsubstituierten Guanidinen zu ermitteln, die gleichzeitig eine hohe Wirksamkeit gegenüber Mehltaupilzen und Pilzen vom Stamme Botrytis besitzen.Fungicides based on N-arylguanidine derivatives, which have a high bactericidal, herbicidal, insecticidal and fungicidal activity, of the general formula are known rin weighed ar is a mono- or poly-cyclic aromatic radical, and which contains various substituents, and R, R '# R "are the same or different lower aliphatic radicals, one of which may be a lower alkoxy group (French Patent No. 1.541.647) The compounds mentioned are, however, produced with the help of more complicated and tougher processes than those proposed below.1 The aim of the present invention is new fungicides based on N, N-di- (or mono) alkyl-N To determine '-aryl-substituted guanidines, which at the same time have a high effectiveness against powdery mildew fungi and fungi of the Botrytis tribe.

Das erwähnte Ziel wurde erreicht durch Verwendung als Fungizide N,N-di-(bzw.-mono)alkyl-N'-arylsubstituierte Guanidine in Form der freien Basen bzw. der Salze der allgemeinen Formeln a) für freie Basen: b) für Salze; worin oder R: H, CH3, C2H5, n-C3H7# i-C3H7, R': CH3, C2H5; n-C2H7, i-C3H7, oder i-C4H9, tert.-C4H9# C5H11, X, y, z: H Cl, Br, CH3, CH3O, oder NO2# CF3; rin wo# R, R', X, Y und Z eine oben gegebene Bedeutung haben, der B:# Säurerest Cl', CH3SO4', (CH3)2NCSS', S4O6" oder C6H3(NO2)3O'.The stated aim was achieved by using N, N-di (or mono) alkyl-N'-aryl-substituted guanidines as fungicides in the form of the free bases or the salts of the general formulas a) for free bases: b) for salts; wherein or R: H, CH3, C2H5, n-C3H7 # i-C3H7, R ': CH3, C2H5; n-C2H7, i-C3H7, or i-C4H9, tert-C4H9 # C5H11, X, y, z: H Cl, Br, CH3, CH3O, or NO2 # CF3; rin where # R, R ', X, Y and Z have a meaning given above, the B: # acid residue Cl', CH3SO4 ', (CH3) 2NCSS', S4O6 "or C6H3 (NO2) 3O '.

Die erwähnten Verbindungen sind weiße kristalline Stoffe'fl-tft Ausnahme der Nitroderivate, die von hellgelb bis rot gefärbt sind. The compounds mentioned are white crystalline substances, an exception of nitro derivatives, which range from light yellow to are colored red.

Von den genannten Verbindungen sind am wirksamsten gegen Mehltaupilze, die Gurken befallen, folgende Stoffe: die Dimethyldithiokarbamate von N,N-Dimethyl-N'-m-chlorphenylguanidin oder N,N-Dimethyl-N'-m-trifluormethylphenylguanidin; das Tetrathionat von N,N'-Dimethyl-N'-m-chlorphenylguanidin; N,N-Dimethyl-N'-m-chlorphenylguanidin; N',N-Dimethyl-N'-p-bromphenylguanidin; N,N-Dimethyl-N'-mtrifluormethylphenylguanidin; N-Methyl-N-äthyl-N'-m-chlorphenylguanidin; N-Methyl-N-äthyl-N'-3,4-dichlorphenylguanidin N-methyl-N-propyl-N'-m-chlorphenylguanidin; N-Methyl-N-butyl-N'-m-chlorphenylguanidin oder N-Methyl-N-butyl-N'-3,4-dichlorphenylguanidin. Diese Stoffe waren wirksam in einer Konzentration von 0,025-0,1% und bekämpfung die Kranlheitsentwicklung bis 80-100%. Of the compounds mentioned, the most effective against powdery mildew fungi, the cucumbers attack the following substances: the dimethyldithiocarbamates of N, N-dimethyl-N'-m-chlorophenylguanidine or N, N-dimethyl-N'-m-trifluoromethylphenylguanidine; the tetrathionate of N, N'-dimethyl-N'-m-chlorophenylguanidine; N, N-dimethyl-N'-m -chlorophenylguanidine; N ', N-dimethyl-N'-p-bromophenylguanidine; N, N-dimethyl-N'-mtrifluoromethylphenylguanidine; N-methyl-N-ethyl-N'-m-chlorophenylguanidine; N-methyl-N-ethyl-N'-3,4-dichlorophenylguanidine N-methyl-N-propyl-N'-m -chlorophenylguanidine; N-methyl-N-butyl-N'-m -chlorophenylguanidine or N-methyl-N-butyl-N'-3,4-dichlorophenylguanidine. These substances were effective in a concentration of 0.025-0.1% and fight disease development up to 80-100%.

bezüglich des Grauschimmels erwiesen sich am wirksams'-en folgende Stoffe: N-Methyl-N'-phenylguanidin; N-tert--Butyl-N'-phenylguanidin; N-Amyl-N'-phenylguanidin; N,N-Dimethyl-N'-m-chlorphenylguanidin; Dimethyldithiokarbamat des N,N-Dimethyl-N'-m-chlorphenylguanidins; N,N-Dimethyl-N'-m-Nitrophenylguanidin; N,N-Dimethyl-N'-3-chloro-4-nitrophenylguanidin; Methylsulfat des N,N-Dimethyl-N'-phenylguanidins; N,N-Dimethyl-N'-p-bromphenylguanidin; N-Methyl-N-propyl-N'-m-trifluormethylphenylguanidin. Die Präparate bekämpfung die Kraiilclieit bis zu 75-96S in Konzentrationen von 0,25% des Wirkstoffs. With regard to gray mold, the following proved to be the most effective Substances: N-methyl-N'-phenylguanidine; N-tert-butyl-N'-phenylguanidine; N-amyl-N'-phenylguanidine; N, N-dimethyl-N'-m -chlorophenylguanidine; Dimethyldithiocarbamate of N, N-dimethyl-N'-m-chlorophenylguanidine; N, N-dimethyl-N'-m-nitrophenylguanidine; N, N-dimethyl-N'-3-chloro-4-nitrophenylguanidine; Methyl sulfate of N, N-dimethyl-N'-phenylguanidine; N, N-dimethyl-N'-p-bromophenylguanidine; N-methyl-N-propyl-N'-m-trifluoromethylphenylguanidine. The preparations fight the Kraiilclieit up to 75-96S in concentrations of 0.25% of the active ingredient.

Die erfindungsgemäßigen Verbindungen können durch Behandlung mit aliphatischen Aminen entsprechender Arylthioharnstoffe, die in Form der Isothiouronsalze genommen sind, gewonnen werden. The compounds according to the invention can by treatment with aliphatic amines of corresponding arylthioureas, which are in the form of isothiouronic salts are taken, are won.

Die erwähnten Verbindungen können auchßdurch Konden- sation gewonnen werden: a) entweder der Monoarylzyanamide mit Hydrochloriden alipha-tischer Amine; b) oder durch Kondensation der Dialkylzynamide mit IIydrochloriden aromatischer Amine. Das erfindungsgemäße Verfahren ist dadurch gekennzeichnet, daß die Ste der IIerstellung der aromatischen Aminhydrochloride mit der Stufe der Konden- sation vereinigen kann; dies, das ganze technologische Schema des Prozesses bedeutend zu vereinfachen #gestattet#.The compounds mentioned can also be The following can be obtained: a) either of the monoarylcyanamides with hydrochlorides of aliphatic amines; b) or by Condensation of dialkyl dynamides with hydrochlorides of aromatic amines. The process according to the invention is characterized in that the stage of the preparation of the aromatic amine hydrochlorides with the stage of condensation sation can unite; this, to significantly simplify the whole technological scheme of the process # allows #.

Die N-monoalkyl-N'-arylsubstituierten Guanidine können auch durch Desulfurierung N-alkyl-N'-arylsubstituierter Thiocharnstoffe und Behandlung der gewonnenen Karb .iimide mit Ammoniak hergestellt werden. The N-monoalkyl-N'-aryl-substituted guanidines can also by Desulfurization of N-alkyl-N'-aryl-substituted thiochureas and treatment of the obtained carbide .iimide are produced with ammonia.

Nach der letzteren Methode werden die N,N'-arylsubstituierten guanidine in Form freißer Basen gewonnen. According to the latter method, the N, N'-aryl-substituted guanidines become obtained in the form of free bases.

Zur Gewinnung von freien Basen der Verbindungen, di nach anderen Verfahren erhalten werden, ist das Auslagen erforderlich. Um Salze zu gewinnen, die sich vom Hydrochlorid und Methylsulfat unterscheiden, muß man die Reaktion der doppelten Zerlegung zwischen dem N,N-arylsubstituierten Guanidinhydrochlorid und dem wasserlöslichen Salz der entsprechenden Säure anwenden, Die erfindungsgemäßen Fungizide gestatten, #wirksam# sowohl die Mehltaupilze als auch den Grauschimmel an Pflanzen zu bekämpfen; dies, die Zahl der Behandlungen mit Präparaten, [erlaubt] welche zur Bekämpfung eines jeden Erregers einzeln verwendet werden,und auch den Aufwand an Präparaten zur Bekämpfung der erwähnten Krankheitserreger zu verringern. Ein großer Vorzug der genannten Fungizide ist die Tatsache, daß sie auf einfache Weise aus einem zugänglichen Rohstoff gewonnen werden können, wodurch die vorgeschlagenen Verbindungen relativ billig sein können. All dies wirkt sich günstig auf den Aufwand an Geldmitteln zur wirksamen Bekämpfung der erwähnten Erreger aus.To obtain free bases of the compounds, that is to say obtained by other processes, expenditure is necessary. In order to obtain salts which differ from the hydrochloride and methyl sulfate, one must apply the double decomposition reaction between the N, N-aryl-substituted guanidine hydrochloride and the water-soluble salt of the corresponding acid the gray mold on plants to fight; this, the number of treatments with preparations, which are used to combat each pathogen individually, and also to reduce the expenditure on preparations to combat the pathogens mentioned. A great advantage of the fungicides mentioned is the fact that they can be obtained in a simple manner from an accessible raw material, as a result of which the proposed compounds can be relatively cheap. All of this has a positive effect on the expenditure of funds to effectively combat the pathogens mentioned.

Um die vorliegende Erfindung zu veranschaulichen, wird nachstehend ein Beispiel zur Herstellung von N,N-Diäthyl-N'-phenylguanidin und Prüfungsbeispiel der vorge schlagen Fungizide angeführt. To illustrate the present invention, below an example for the preparation of N, N-diethyl-N'-phenylguanidine and test example of the suggested fungicides.

Beispiel Herstellung von N,N-Diäthyl-N phenylguanidin In den Reaktionskolben werden 81,4 g (0,874 Mol) Anilin, 90,0 g (0,919 Mol) Diäthylzyanamid und 170 g Toluol eingeführt. Das Gemisch wird bis 90-95°C erwärmt, und unter Rühren werden im Laufe von zwei Stunden 33,5 g (0,919 Mol) Chlorwasserstoff zugelassen. Das Reaktionsgemisch wird vier Stunden bei schwachem Sieden und Rühren zur Abklingen der Reaktion gehalten. Die Siedetemperatur des Reaktionsgemisches ist zu Beginn der REaktion gleich 118°C und am Ende 113--115°C. Nach Abschluß der Haltezeit wird die Reaktionsmasse Vorsichtig werden dann bis 98-100°C abgekühlt. 200 ml Wasser zur Auflösung des sich bildenden N,N-Diäthyl-N'-phenylguanidinhydrochlorids zugegeben; man kühlt weiter bis 20-250C ab und bringt den pH-Wert des Mediums auf 7,5-8,0 durch Zugabe einer wässerigen Ätznatronlösung. Die Reaktionsmasse läßt man abstehen, und trennt die wässerige Schicht, die das N,N-Dic£ß äthyl-N'-phenylguanidinhydrochlorid enthält, ab. Example Preparation of N, N-diethyl-N phenylguanidine In the reaction flask 81.4 g (0.874 mol) of aniline, 90.0 g (0.919 mol) of diethyl cyanamide and 170 g of toluene are obtained introduced. The mixture is heated to 90-95 ° C, and with stirring 33.5 g (0.919 mol) of hydrogen chloride are admitted in the course of two hours. The reaction mixture is allowed to subside for four hours with gentle boiling and stirring the reaction kept. The boiling point of the reaction mixture is at the beginning the reaction equals 118 ° C and at the end 113--115 ° C. After the hold time is over, the reaction mass is then carefully cooled to 98-100 ° C. 200 ml of water added to dissolve the N, N-diethyl-N'-phenylguanidine hydrochloride which forms; the mixture is cooled further to 20-250C and the pH of the medium is brought to 7.5-8.0 Addition of an aqueous solution of caustic soda. The reaction mass is allowed to stand, and separates the aqueous layer containing the N, N-Dic £ ß ethyl-N'-phenylguanidine hydrochloride contains, from.

Die.wässerige Schicht wird in den Reaktionskolben eingeführt und G.r Rühren und Abkühlen eine 2O%ige wässerige Ätznatronlösung (36 g NaOH, 0,9 Lol) zugegeben. The aqueous layer is introduced into the reaction flask and G.r stirring and cooling a 2O% aqueous caustic soda solution (36 g NaOH, 0.9 Lol) admitted.

Die sich bildende freie N,N-Diäthyl-N'-phenylguanidinbase kristallisiert sich beim lmpfcn Es wurden 127,0 g des Stoffes mit einem Schmp. 56-58°C erhalten.The free N, N-diethyl-N'-phenylguanidine base that forms crystallizes 127.0 g of the substance with a melting point of 56.degree.-58.degree. C. were obtained.

Der Gehalt an Wirkstoff betrug bei nitrierung mit 0,2 n-Salzsäure 98,8%. Die Ausbeute war gleich 75,1%. The active ingredient content was 0.2 N hydrochloric acid when nitrated 98.8%. The yield was equal to 75.1%.

Analog können auch die anderen N,N-Diäthyl-N'-arylguanidine hergestellt werden.The other N, N-diethyl-N'-arylguanidines can also be prepared analogously will.

Prüfung 1: Die Wirksamkeit der Präparate wurde im Treibhaus bei der Bekämpfung von Mehltaupilzen, die Gurken befallen (Brysiphe cichoracearum D.C. f-cucurbitacearum Pot. u Sphaerotheca fuliginea Poll. f. cucurbitacearum Pot.) geprüft. Pflanzen mit einigen ausgeformten Blättern wurden mit Suspension non der Präparate bespritzt; nach ihrer Trocknung wurden die blätter mit der Pilzkonidiensuspension mit einer Infektionsbelastung 200 000 Konidien in einem cm³ inokuliert. als Etalon diente 25%iges Karathan. Der Versuch wurde dreimal wiederholt. Test 1: The effectiveness of the preparations was tested in the greenhouse Combating powdery mildew fungi that attack cucumbers (Brysiphe cichoracearum D.C. f-cucurbitacearum Pot. u Sphaerotheca fuliginea Poll. f. cucurbitacearum Pot.). Plants with Some of the formed leaves were sprayed with suspension of the preparations; After drying, the leaves with the mushroom conidia suspension were treated with a Infection load 200,000 conidia inoculated in one cm³. served as a standard 25% Karathan. The experiment was repeated three times.

Die Prüfungsergebnisse der Verbindungen, verwendet in Form 50%iger benetztbarer Pulver gegen Mehltaupilze an Gurken, sind in Tabellen 1-8 angeführt Die in den Tabellen angeführten tivität Konzentration entsprechen der Ak der Wirkstoffe Wie aus Tabelle 1 und 2 zu ersehen ist, zeigten die N,N-dimethyl-N'-arylsubstituierten Guanidine eine hohe Aktivität gegenüber Mehtaupiluen an Gruken. Die höchste wirksamkeit wurde bei N,N-Dimethyl-N'-m-chlorphenylguanidin, N,N-Dimethyl-N'-p-chlorphenylguanidin, N,N-Dimethyl-N'-3,4-dichlorphenylguanidin, N,N-Dimethyl-N'-p-bromphenylguanidin und N,N-Dimethyl-N'-m-trifluormethylphenylguanidin beobachtet. Die Aktivität dieser Verbindungen war gleich 6der nahe zum Karaan. The test results of the compounds, used in the form of 50% wettable powder against powdery mildew on cucumber are listed in Tables 1-8 The activity concentration listed in the tables correspond to the Ab of the active ingredients As can be seen from Tables 1 and 2, the N, N-dimethyl-N'-aryl-substituted Guanidines have a high activity against Mehtaupiluen on Gruken. The highest effectiveness was at N, N-dimethyl-N'-m-chlorophenylguanidine, N, N-dimethyl-N'-p-chlorophenylguanidine, N, N-dimethyl-N'-3,4-dichlorophenylguanidine, N, N-dimethyl-N'-p-bromophenylguanidine and N, N-dimethyl-N'-m-trifluoromethylphenylguanidine was observed. The activity of this Connections was the same 6der close to the Karaan.

Die Untersuchung von N,N-dimethyl-N'-arylsubstituierten Guanidinsalzen zeigte, daß sie alle eine hohe Aktivität gegen Mehltaupilze an Gurken besitzen (Tabelle 3). The study of N, N-dimethyl-N'-aryl-substituted guanidine salts showed that they all have high activity against powdery mildew fungi on cucumbers (Table 3).

Pikarat des Das Dimethyldithiokarbamat und das N,N-Dimethyl-N'-m-chlorphenylguanidins wie auch das Dimethyl dithi okarbamat des N,N-Dimethyl-N'-m-trifluormethylphenylguanidins zeigten eine Wirksamkeit, die gleich oder nahe zum Karathan war.Picarate of the dimethyldithiocarbamate and the N, N-dimethyl-N'-m-chlorophenylguanidine as well as the dimethyl dithiocarbamate of N, N-dimethyl-N'-m-trifluoromethylphenylguanidine showed an effectiveness equal to or close to the Karathan.

Die N,N-diäthyl-N'-arylsubstituierten Guanidine zeigten eine hohe Wirksamkeit gegen Mehltaupilze an Gurken in Konzentrationen 0,05 - 0,2%, waren jedoch schwächer als das Karathan (Tabelle 4). The N, N-diethyl-N'-aryl-substituted guanidines showed a high level Efficacy against powdery mildew fungi on cucumbers in concentrations of 0.05-0.2%, however, were weaker than the Karathan (Table 4).

Die N,N-dipropyl-N'-arylsubstituierten Guanidine zeigten eine hohe Aktivität bei der Bekämpfung von Liehltaupilzen an Gurken. Von den Präparaten dieser Gruppe war das N,N-Dipropyl-N'-m-trifluormethylphenylguanidin der Wirksamkeit nach nade dem Karathan (Tabelle 5). The N, N-dipropyl-N'-aryl-substituted guanidines showed a high Activity in the control of beach dew fungi on cucumbers. From the preparations of this The group was the N, N-Dipropyl-N'-m-trifluoromethylphenylguanidine for effectiveness nade the Karathan (Table 5).

Die N-methyl-N-alkyl-N'-arylsubstituierten Guanidina waren stark aktiv gegen Mehltaupilze an Gurken (Tabelle 6 und 7). Von ihnen waren N-Methyl-N-äthyl-N'-m-chlorphenylguanidin, N-Methyl-N-äthyl-N'-3,4-dichlorphenylguanidin, N-Methyl-N-propyl-N'-m-chlorphenylguanidin, N-Methyl-N-propyl-N'-m-trifluormethylphenylguanidin und N-Methyl-N-butyl-N'-m-chlorphenylguanidin der Wirksamkeit nach gleich bzw. nahe dem Karatnan. The N-methyl-N-alkyl-N'-aryl substituted guanidines were strong active against powdery mildew on cucumbers (Tables 6 and 7). Of them were N-methyl-N-ethyl-N'-m-chlorophenylguanidine, N-methyl-N-ethyl-N'-3,4-dichlorophenylguanidine, N-methyl-N-propyl-N'-m-chlorophenylguanidine, N-methyl-N-propyl-N'-m-trifluoromethylphenylguanidine and N-methyl-N-butyl-N'-m -chlorophenylguanidine the Effectiveness equal to or close to the karatnan.

Die N-Alkyl-N'-arylguanidine zeigten eine hohe Aktivität gegen Mehltau n.r. in Konzentrationen von 0,1 und 0,2% (Ta von belle b). In Konzentrationen 0,05 und 0,025% waren sie jedoch ungenügend wirksam. The N-alkyl-N'-arylguanidines showed high activity against powdery mildew No. in concentrations of 0.1 and 0.2% (Ta from belle b). In concentrations 0.05 and 0.025%, however, they were insufficiently effective.

Prüfung 2: Eine der aktivsten Verbindungen - das N,N-Dimethyl-N'-m-chlorphenylguanidin - wurde bei der Bekämpfung von Mehl taupilzen an Äpfeln (Sorte Jonathan) in Form eines 50%igen benetzbaren Pulvers untersucht. Das Präparat wurde in einer Konzentration von 0,15% des Wirkstoffes und der 90%ige von Schwefel (Etalon) in einer Konzentration 0,45% des Wirkstoffes geprüft. Während einer Saison wurden sechs Bespritzungen durchgeführt. Die Versuchsergebnisse sind in tabelle 9 angeführt. Test 2: One of the most active compounds - the N, N-dimethyl-N'-m-chlorophenylguanidine - was used in the fight against flour dew on apples (variety Jonathan) in the form investigated a 50% wettable powder. The preparation was in one concentration of 0.15% of the active ingredient and 90% of sulfur (Etalon) in one concentration 0.45% of the active ingredient tested. Six sprayings were carried out during one season. The test results are shown in table 9.

Wie aus Tabelle 9 zu ersehen ist, zeigte das N,N-Di Methyl-N'-m-chlorphenylguanidin bei der Bekämpfung des Wenltaupilzes an Äpfeln eine Effektivität, die dem benetzbaren Schwefel gleichkommt, wobei das erwähnte Präparat in einer dreifach geringeren Konzentration verwendet wurde, als der Schwefel. As can be seen from Table 9, this showed N, N-di methyl-N'-m -chlorophenylguanidine in combating the Wenltaupfilz on apples an effectiveness that the wettable Sulfur equals, the mentioned preparation in a three times lower concentration was used as the sulfur.

Präfung 3: Die Wirksamkeit der Präparate bei der Bekämpfung von Sotrytis fabae in Treibhäusern wunde an Bohnen der Sorto ,;Russische Schwarze" untersucht. Für die Versuche wurden Pflanzen genommen, die 7-8 Paar gutentwickelter Blätter hatten. Die Präparate und das Captan (Etalon) wurden in 0,25%iger Konzentration des Wirkstoffes geprüft, Die Pflanzen wurden zu Beginn mit einer Suspension des Präparates bespritzt. Nach dem Austrocknen der Suspension des Präparate wurden die Pflanzen mit einer Suspension von Sporen Botrytis Cabae, gewonnen aus einer reinen, auf Haferagar gezüchteten Pilzkultur, inokuliert. Die Registerierung der auftauchenden Erkrankung wurde am dritten Tage nach folgender Methode durchgeführt: Es wurden die Nekrosen auf jedem Blatt auf einer Kreisfläche mit einem Durchinesser 1,5 cm gezählt. Danach wurde der Prozentsatz der Krankheitsbekampfung nach der Abbott-Formel berechnet. Die Versuchsergebnisse sind in Tabellen 10-16 angeführt. Test 3: The effectiveness of the preparations in combating Sotrytis fabae in hothouses wounded on Sorto beans ,; Russian blacks " examined. Plants were used for the experiments, which were 7-8 pairs more well developed Had leaves. The preparations and the captan (Etalon) were in 0.25% concentration the active ingredient tested, the plants were at the beginning with a suspension of the Splashed preparation. After the suspension of the preparation had dried out, the Plants with a suspension of Botrytis Cabae spores obtained from a pure, fungal culture grown on oat agar, inoculated. The registration of the emerging Illness was carried out on the third day according to the following method: There were the necroses on each leaf on a circular area with a diameter of 1.5 cm counted. After that, the percentage of disease control was calculated using the Abbott formula calculated. The test results are given in Tables 10-16.

Die Prüfung der N,N-dimethyl-N'-arylsubstituiertten Guanidine zeigte, daß sie eine hohe Wirksamkeit bei der Bekämpfung von Botrytis fabae der bohnen besitzen (Tabelle 10). Von den Präparaten dieser Gruppe bekämpften N,N-Dimethyl-N'-m-chlorphenylguanidin, N,N-Dimethyl-N-m-nitrophenylguanidin, N,N-Dimethyl-N-p-nitrophenylguanidin, N,N-Dimethyl-N'-3-chlor-4-nitrophenylguanidin, N,N-Dimethyl-N'-4-chlor-3-nitrophenylguanidin und N, Dimethyl-N'-3-nitro-4-methyl-phenylguanidin die Krankheit ebenso wie das Captan. Examination of the N, N-dimethyl-N'-aryl-substituted guanidines showed that they are highly effective in combating Botrytis fabae of the beans (Table 10). Of the preparations in this group, N, N-dimethyl-N'-m-chlorophenylguanidine, N, N-dimethyl-N-m-nitrophenylguanidine, N, N-dimethyl-N-p-nitrophenylguanidine, N, N-dimethyl-N'-3-chloro-4-nitrophenylguanidine, N, N-dimethyl-N'-4-chloro-3-nitrophenylguanidine and N, Dimethyl-N'-3-nitro-4-methyl-phenylguanidine the disease as well as the captan.

Wie aus den Ergebnissen der Tabelle 11 ersichtlich ist, wurde eine hohe Wirksamkeit beim Dimethyldithiocarbamat des N,N-Dimethyl-N'-m-chlorphenylguanidins beim Schutz der Bohnen gegen Botrytis fabae beobachtet. Dieses Präparat war der Aktivität nach dem Captan gleich. Das Methylsulfat des N,N-Dimethyl-N'-phenylguanidins war schwächer als das Captan (Tabelle 12). As can be seen from the results in Table 11, a high effectiveness with the dimethyldithiocarbamate of N, N-dimethyl-N'-m-chlorophenylguanidine observed in protecting the beans against Botrytis fabae. This preparation was the Activity right after the captan. The methyl sulfate of N, N-dimethyl-N'-phenylguanidine was weaker than the captan (Table 12).

Aus den Ergebnissen der iabelle 13 ist zu ersehen, daß N,N-Dipropyl-N'-phenylguanidin, N,N-Dipropyl-N'--p-chlorophenylguanidin und N,N-Dipropyl-N'-p-bromphenylguanidin eine hohe Aktivität gegen Botrytis fabae an Bohnen besitzen, jedoch weniger wirksam als das Captan waren. From the results of Table 13 it can be seen that N, N-Dipropyl-N'-phenylguanidine, N, N-dipropyl-N'-p -chlorophenylguanidine and N, N-dipropyl-N'-p-bromophenylguanidine have high activity against Botrytis fabae on beans, but less effective when the captan were.

N-Methyl-N-äthyl-N'-p-chlorphenylguanidin, N-Methyl-N-äthyl-N'-bromphenylguanidin und N-Methyl N-propyl-N'-m-trifluormethylphenylguanidin zeigteneine Wirksamkeit nahe dem Captan (Tabelle 14 und 15). N-methyl-N-ethyl-N'-p-chlorophenylguanidine, N-methyl-N-ethyl-N'-bromophenylguanidine and N-methyl N-propyl-N'-m-trifluoromethylphenylguanidine showed activity near the captan (Tables 14 and 15).

N-Alkyl-N'-phenylguanidine zeigten bei Prüfungen gegen Botrytis fabae an Bohnen eine Wirksamkeit, die dem daptan gleich war (Tabelle 16). N-alkyl-N'-phenylguanidines showed in tests against Botrytis fabae an effectiveness on beans that was equal to that of daptan (Table 16).

Tabelle 1 Lfd. Konzentra- Krankheits- Nr. Präparate tion % bekämpfung % 1 2 3 4 1 N,N-Dimethyl-N'-phenyl- 0,025 70,0 guanidin 0,05 73,0 0,1 82,0 0,2 90,0 2 Methylsulfat des N,N-Di- 0,025 50,0 methyl-N'-phenylguanidins 0,05 68,0 0,1 70,0 0,2 80,0 3 N,N-Dimethyl-N'-m-chlor- 0,025 79,0 phenylguanidin 0,05 93,0 0,1 97,0 0,2 100,0 4 N,N-Dimethyl-N'-m-chlor- 0,025 87,0 phenylguanidin 0,05 96,0 0,1 99,0 0,2 100,0 5 N,N-Dimethyl-N'-p-chlor- 0,025 93,0 phenylguanidin 0,05 97,0 209883/1136 0,1 j 100,0 0,2 4 100,0 1 2 3 4 6 N,N-Dimethyl-N'-2,5- 0,025 59,0 dichlorphenylguanidin 0,05 74,0 0,1 83,0 0,2 100,0 7 N,N-Dimethyl-N'-3,4-di- 0,025 88,0 chlorphenylguanidin 0,05 94,0 0,1 100,0 0,2 100,0 8 N,N-Dimethyl-N'-2,5- 0,025 55,0 chlorphenylguanidin 0,05 77,0 0,1 97,0 0,2 100,0 9 N,N-Dimethyl-N'-2,5- 0,025 79,0 phenylguanidin 0,05 93,0 0,1 99,0 0,2 100,0 10 N,N-Dimethyl-N'-2,5- 0,025 88,0 methylphenylguanidin 0,05 97,0 0,1 100,0 0,2 100,0 h 11 Karat#an (Etalon) 0,025 97,0 0,05 100,0 Krankheitsentwicklung in der Probe 71% Tabelle 2 Ldf. Konzentra- Krankheits- Nr. Präparate tion % bekämpfung % 1 2 3 4 1 N,N-Dimethyl-N'-m-methyl- 0,025 66,0 phenylguanidin 0,05 85,0 0,1 100,0 0,2 100,0 2 N,N-Dimethyl-N'-p-methyl- 0,025 67,0 phenylguanidin 0,05 79,0 0,1 93,0 0,2 98,0 3 N,N-Dimethyl-N'-m-methyl- 0,025 64,0 thoxyphenylguanidin 0,05 77,0 0,1 95,0 0,2 99,0 4 N,N-Dimethyl-N'-m-nitro- 0,025 73,0 phenylguanidin 0,05 83,0 0,1 94,0 0,2 100,0 5 N,N-Dimethyl-N'-m-methyl- 0,025 57,0 phenylguanidin 0,05 80,0 0,1 94,0 0,2 96,0 1 j 2 j 3 t 4 6 N,N-Dimethyl-N'-2-nitro- 0,025 58,0 -4-methylphenylguanidin 0,05 66,0 0,1 83,0 0,2 89,0 7 N,N-Dimethyl-N'-3-nitro- 0,025 49,0 -4-methylphenylguanidin 0,05 74,0 0,1 87,0 0,2 94,0 8 N,N-Dimethyl-N'-2-chlor- 0,025 56,0 -4-nitrophenylguanidin 0,05 72,0 0,1 87,0 0,2 93,0 9 N,N-Dimethyl-N'-4-chlor- 0,025 55,0 -3-nitrophenylguanidin 0,05 78,0 0,1 100,0 0,2 100,0 10 Karathan (Etalon) 0,025 87,0 0,05 96,0 Krankheitsentwicklung in der Probe 75%. Lfd. Konzentra- Krankheits- Nr. Präparate tion % bekämpfung % 1 2 3 4 1 N,N-Dimethyl-N'-m-chlor- 0,025 85,0 phenylguanidin 0,05 97,0 0,1 98,0 0,2 100,0 2 Dimethyldithiokarbamat 0,025 89,0 des N,N-Dimethyl-N'-m- 0,05 96,0 -chlorphenylguanidins 0,1 98,0 0,2 100,0 3 N,N-Dimethyl-N'-m-chlor- 0,025 83,0 phenylguanidintetrathionat 0,05 94,0 0,1 98,0 0,2 100,0 4 N,N-Dimethyl-N'-m-chlor- 0,025 58,0 phenylguanidinpikrat 0,05 72,0 0,1 89,0 0,2 99,0 5 Dimethyldithiokarbamat 0,025 94,0 des N,N-Dimethyl-N'-m- 0,05 98,0 -trifluormethylphenyl 0,1 100,0 guanidins 0,2 100,0 h 6 Karat#an (Etanol) 0,025 95,0 0,05 98,0 Krankheitsentwicklung in der Probe 87%.Table 1 Serial Concentration Disease No. Preparation% control% 1 2 3 4 1 N, N-dimethyl-N'-phenyl-0.025 70.0 guanidine 0.05 73.0 0.1 82.0 0.2 90.0 2 N, N-Di-0.025 50.0 methyl sulfate methyl-N'-phenylguanidine 0.05 68.0 0.1 70.0 0.2 80.0 3 N, N-dimethyl-N'-m -chloro-0.025 79.0 phenylguanidine 0.05 93.0 0.1 97.0 0.2 100.0 4 N, N-dimethyl-N'-m -chloro-0.025 87.0 phenylguanidine 0.05 96.0 0.1 99.0 0.2 100.0 5 N, N-dimethyl-N'-p -chloro-0.025 93.0 phenylguanidine 0.05 97.0 209883/1136 0.1 j 100.0 0.2 4 100.0 1 2 3 4 6 N, N-dimethyl-N'-2.5-0.025 59.0 dichlorophenylguanidine 0.05 74.0 0.1 83.0 0.2 100.0 7 N, N-dimethyl-N'-3,4-di-0.025 88.0 chlorophenylguanidine 0.05 94.0 0.1 100.0 0.2 100.0 8 N, N-dimethyl-N'-2.5-0.025 55.0 chlorophenylguanidine 0.05 77.0 0.1 97.0 0.2 100.0 9 N, N-dimethyl-N'-2.5-0.025 79.0 phenylguanidine 0.05 93.0 0.1 99.0 0.2 100.0 10 N, N-dimethyl-N'-2.5-0.025 88.0 methylphenylguanidine 0.05 97.0 0.1 100.0 0.2 100.0 H 11 carat # at (etalon) 0.025 97.0 0.05 100.0 Disease development in the sample 71% Table 2 Ldf. Concentration Disease No. Preparation% control% 1 2 3 4 1 N, N-dimethyl-N'-m-methyl-0.025 66.0 phenylguanidine 0.05 85.0 0.1 100.0 0.2 100.0 2 N, N-dimethyl-N'-p -methyl-0.025 67.0 phenylguanidine 0.05 79.0 0.1 93.0 0.2 98.0 3 N, N-dimethyl-N'-m-methyl-0.025 64.0 thoxyphenylguanidine 0.05 77.0 0.1 95.0 0.2 99.0 4 N, N-dimethyl-N'-m-nitro-0.025 73.0 phenylguanidine 0.05 83.0 0.1 94.0 0.2 100.0 5 N, N-dimethyl-N'-m-methyl-0.025 57.0 phenylguanidine 0.05 80.0 0.1 94.0 0.2 96.0 1 j 2 j 3 t 4 6 N, N-dimethyl-N'-2-nitro-0.025 58.0 -4-methylphenylguanidine 0.05 66.0 0.1 83.0 0.2 89.0 7 N, N-dimethyl-N'-3-nitro-0.025 49.0 -4-methylphenylguanidine 0.05 74.0 0.1 87.0 0.2 94.0 8 N, N-dimethyl-N'-2-chloro-0.025 56.0 -4-nitrophenylguanidine 0.05 72.0 0.1 87.0 0.2 93.0 9 N, N-dimethyl-N'-4-chloro-0.025 55.0 -3-nitrophenylguanidine 0.05 78.0 0.1 100.0 0.2 100.0 10 Karathan (Etalon) 0.025 87.0 0.05 96.0 Disease development in the sample 75%. Serial Concentration Disease No. Preparation% control% 1 2 3 4 1 N, N-dimethyl-N'-m -chloro-0.025 85.0 phenylguanidine 0.05 97.0 0.1 98.0 0.2 100.0 2 dimethyl dithiocarbamate 0.025 89.0 des N, N-dimethyl-N'-m-0.05 96.0 -chlorophenylguanidine 0.1 98.0 0.2 100.0 3 N, N-dimethyl-N'-m -chloro-0.025 83.0 phenylguanidine tetrathionate 0.05 94.0 0.1 98.0 0.2 100.0 4 N, N-dimethyl-N'-m -chloro-0.025 58.0 phenylguanidine picrate 0.05 72.0 0.1 89.0 0.2 99.0 5 dimethyl dithiocarbamate 0.025 94.0 des N, N-dimethyl-N'-m-0.05 98.0 -trifluoromethylphenyl 0.1 100.0 guanidines 0.2 100.0 H 6 carat # of (ethanol) 0.025 95.0 0.05 98.0 Disease development in the sample 87%.

Tabelle 4 Lfd. Konzentra- Krankheitsbe- Nr. Präparate tion % kämpfung % 1 2 3 4 1 N,N-Diäthyl-N'-phenyl- 0,025 59,0 guanidin 0,05 63,0 0,1 75,0 0,2 84,0 2 N,N-Diäthyl-N'-m-chlor- 0,025 66,0 phenylguanidinhydrochlo- 0,05 89,0 rid 0,1 97,0 0,2 99,0 3 N,N-Diäthyl-N'-2,5-di- 0,025 72,0 chlorphenylguanidin 0,05 78,0 0,1 88,0 0,2 97,0 4 N,N-Diäthyl-N'-2,5-dichlor- 0,025 68,0 phenylguanidinhydrochlo- 0,05 80,0 rid 0,1 91,0 0,2 96,0 N,N-Diäthyl-N'-3,4-di- 0,025 69,0 chlorphenylguanidinhydro- 0,05 86,0 chlorid 0,1 95,0 0,2 100,0 1 2 3 4 6 N,N-Diäthyl-N'-2,4,5- 0,025 57,0 -trichlorphenylguanidin 0,05 69,0 0,1 97,0 0,2 100,0 7 N,N-Diäthyl-N'-p-brom- 0,025 57,0 phenylguanidin 0,05 80,0 0,1 88,0 0,2 98,0 8 N,N-Diäthyl-N'-m-tri- 0,025 76,0 fluormethylphenylguani- 0,05 88,0 dinhydrochlorid 0,1 94,0 0,2 99,0 9 N,N-Diäthyl-N'-p-nitro- 0,025 53,0 phenylguanidin 0,05 65,0 0,1 93,0 0,2 100,0 10 N,N-Diäthyl-N'-3-chlor- 0,025 48,0 -trichlorphenylguanidin 0,05 70,0 0,1 75,0 0,2 84,0 h 11 Karat#an (Etalon) 0,025 92,0 0,05 97,0 Krankheitsentwicklung in der Probe 75% Tabelle 5 Lfd. Konzentra- Krankheits- Nr. Präparate tion % bekämpfung % 1 2 3 4 1 N,N-Dipropyl-N'-phenyl- 0,025 56,0 guanidin 0,05 69,0 0,1 80,0 0,2 96,0 2 N,N-Dipropyl-N'-m-chlor- 0,025 63,0 guanidin 0,05 80,0 0,1 85,0 0,2 87,0 3 N,N-Dipropyl-N'-3,4-di- 0,025 63,0 chlorphenylguanidin 0,05 82,0 0,1 88,0 0,2 90,0 4 N,N-Dipropyl-N'-3,4-di- 0,025 66,0 chlorphenylguanidin 0,05 83,0 0,1 96,9 0,2 97,5 5 N,N-Dipropyl-N'-2,5-di- 0,025 5960 chlorphenylguanidin 0,05 63,0 0,1 85,0 0,2 91,0 1 2 3 4 6 N,N-Dipropyl-N'-p-brom- 0,025 55,0 phenylguanidin 0,05 74,Ö 0,1 82,0 0,2 93,0 N,N-Dipropyl-N'-m-tri- 0,025 87,0 fluormethylphenylguani- 0,05 93,0 din 0,1 100,0 0,2 100,0 8 karathan (Etalon) 0,025 96,0 0,05 100,0 Krankheitsentwicklung in der Probe 87%.Table 4 Serial Concentration Disease No. preparation% fighting% 1 2 3 4 1 N, N-diethyl-N'-phenyl-0.025 59.0 guanidine 0.05 63.0 0.1 75.0 0.2 84.0 2 N, N-diethyl-N'-m -chloro-0.025 66.0 phenylguanidine hydrochloride 0.05 89.0 rid 0.1 97.0 0.2 99.0 3 N, N-diethyl-N'-2,5-di-0.025 72.0 chlorophenylguanidine 0.05 78.0 0.1 88.0 0.2 97.0 4 N, N-diethyl-N'-2,5-dichloro-0.025 68.0 phenylguanidine hydrochloride 0.05 80.0 rid 0.1 91.0 0.2 96.0 N, N-diethyl-N'-3,4-di-0.025 69.0 chlorophenylguanidine hydro- 0.05 86.0 chloride 0.1 95.0 0.2 100.0 1 2 3 4 6 N, N-diethyl-N'-2,4.5-0.025 57.0 -trichlorophenylguanidine 0.05 69.0 0.1 97.0 0.2 100.0 7 N, N-diethyl-N'-p-bromo-0.025 57.0 phenylguanidine 0.05 80.0 0.1 88.0 0.2 98.0 8 N, N-diethyl-N'-m-tri- 0.025 76.0 fluoromethylphenylguani- 0.05 88.0 din hydrochloride 0.1 94.0 0.2 99.0 9 N, N-diethyl-N'-p -nitro-0.025 53.0 phenylguanidine 0.05 65.0 0.1 93.0 0.2 100.0 10 N, N-diethyl-N'-3-chloro-0.025 48.0 -trichlorophenylguanidine 0.05 70.0 0.1 75.0 0.2 84.0 H 11 carat # an (etalon) 0.025 92.0 0.05 97.0 Disease development in the sample 75% Table 5 Serial Concentration Disease No. Preparation% control% 1 2 3 4 1 N, N-dipropyl-N'-phenyl-0.025 56.0 guanidine 0.05 69.0 0.1 80.0 0.2 96.0 2 N, N-dipropyl-N'-m -chloro-0.025 63.0 guanidine 0.05 80.0 0.1 85.0 0.2 87.0 3 N, N-dipropyl-N'-3,4-di-0.025 63.0 chlorophenylguanidine 0.05 82.0 0.1 88.0 0.2 90.0 4 N, N-dipropyl-N'-3,4-di-0.025 66.0 chlorophenylguanidine 0.05 83.0 0.1 96.9 0.2 97.5 5 N, N-dipropyl-N'-2,5-di-0.025 5960 chlorophenylguanidine 0.05 63.0 0.1 85.0 0.2 91.0 1 2 3 4 6 N, N-dipropyl-N'-p-bromo-0.025 55.0 phenylguanidine 0.05 74, Ö 0.1 82.0 0.2 93.0 N, N-dipropyl-N'-m-tri- 0.025 87.0 fluoromethylphenylguani- 0.05 93.0 din 0.1 100.0 0.2 100.0 8 karathan (etalon) 0.025 96.0 0.05 100.0 Disease development in the sample 87%.

Tabelle 6 Lfd. Konzentra- Krankheits- Nr. Präparate tion % bekämpfung % 1 2 3 4 1 N-Methyl-N-äthyl-N'- 0,025 86,0 -m-chlorphenylguanidin 0,05 97,0 0,1 100,0 0,2 100,0 2 N-Methyl-N-äthyl-N'-p- 0,025 78,0 chlorphenylguanidin 0,05 91,0 0,1 100,0 0,2 100,0 3 N-Methyl-N-äthyl-N'- 0,025 68,0 -2,5-dichlorphenylguani- 0,05 84,0 0,1 100,0 0,2 100,0 4 N-Methyl-N-äthyl-N'- 0,025 92,0 -3,4-dichlorphenylguani- 0,05 97,0 din 0,1 100,0 0,2 100,0 5 N-Methyl-N-äthyl-N'-2- 0,025 79,0 4,5-trichlorphenylguani- 0,05 85,0 din 0,1 89,0 0,2 96,0 1 2 3 4 6 N-Methyl-N-äthyl-N'-p- 0,025 68,0 -bromphenylguanidin O,05 77,0 0,1 94,0 0,2 100,0 . 7 N-Methyl-N-äthyl-N'-m- 0,025 73,0 trifluormethylphenyl- 0,05 84,0 guanidin 0,1 92,0 0,2 97,0 8 N-Methyl-N-äthyl-N'-p- 0,025 57,0 -methylphenylguanidin 0,05 66,0 0,1 94,0 0,2 100,0 9 N-Methyl-N-äthyl-N'-p- 0,025 50,0 -nitrophenylguanidin O,05 67,0 0,1 85,0 0,2 93,0 h 10 Karat#an (Etalon) 0,025 96,0 0,05 100,0 Krankheitsentwicklung in der Probe 87%.Table 6 Serial Concentration Disease No. Preparation% control% 1 2 3 4 1 N-methyl-N-ethyl-N'-0.025 86.0 -m-chlorophenylguanidine 0.05 97.0 0.1 100.0 0.2 100.0 2 N-methyl-N-ethyl-N'-p-0.025 78.0 chlorophenylguanidine 0.05 91.0 0.1 100.0 0.2 100.0 3 N-methyl-N-ethyl-N'-0.025 68.0 -2,5-dichlorophenylguani- 0.05 84.0 0.1 100.0 0.2 100.0 4 N-methyl-N-ethyl-N'-0.025 92.0 -3,4-dichlorophenylguani- 0.05 97.0 din 0.1 100.0 0.2 100.0 5 N-methyl-N-ethyl-N'-2-0.025 79.0 4,5-trichlorophenylguani- 0.05 85.0 din 0.1 89.0 0.2 96.0 1 2 3 4 6 N-methyl-N-ethyl-N'-p-0.025 68.0 -bromophenylguanidine 0.05 77.0 0.1 94.0 0.2 100.0 . 7 N-methyl-N-ethyl-N'-m-0.025 73.0 trifluoromethylphenyl-0.05 84.0 guanidine 0.1 92.0 0.2 97.0 8 N-methyl-N-ethyl-N'-p-0.025 57.0 -methylphenylguanidine 0.05 66.0 0.1 94.0 0.2 100.0 9 N-methyl-N-ethyl-N'-p-0.025 50.0 -nitrophenylguanidine 0.05 67.0 0.1 85.0 0.2 93.0 H 10 carat # an (etalon) 0.025 96.0 0.05 100.0 Disease development in the sample 87%.

Tabelle 7 Lfd. Konzentra- Krankheits- Nr. Präparate tion % bekämpfung 1 2 3 4 1 N-Methyl-N-propyl-N'- 0.025 86.0 -m-chlorphenylguanidin 0.05 92.0 0.1 98.0 0.2 100.0 2 N-Methyl-N-propyl-N'-m- 0.025 82.0 trifluormethylphenyl- 0.05 91.0 guanidin 0.1 98.0 0.2 100.0 3 N-Methyl-N-isopropyl- 0.025 57.0 N'-m-chlorphenylguani- 0.05 70.0 din 0.1 87.0 0.2 100.0 4 N-Methyl-N-butyl-N'-m- 0.025 85.0 -chlorphenylguanidin 0.05 93.0 0.1 98.0 0.2 100.0 5 N-Methyl-N-butyl-N'-p- 0.025 45.0 -nitrophenylguanidin 0.05 59.0 0.1 82.0 0.2 90.0 6 Karathan (Etalon) 0.025 93.0 0.05 98.0 Krankheitsentwicklung i in der Probe 87,0%. - Tabelle 8 Lfd. Konzentra- Krankheits- Nr. Präparate tion % bekämpfung % 1 2 3 4 1 N-Methyl-N'-phenyl- 0,025 44,0 guanidin 0,05 52,0 0,1 80,0 0,2 93,0 2 N-Äthyl-N'-phenyl- 0,025 45,0 guanidin 0.05 53.0 0.1 78.0 0.2 88.0 N-Isopropyl-N'-phenyl- 0.025 34.0 guanidin 0.05 59.0 0.1 79.0 0,2 81,0 4 ,N-Isobutyl-N'-phenyl 0,025 43,0 guanidin 0,05 47,0 0,1 75,0 0,2 84,0 5 N-sek-Butyl-N'-phenyl- O,025 49,0 guanidin # 0,05 59,0 0,1 77,0 0.2 82.0 2 3 4 6 N-tert-Butyl-N'-phenyl- 0,025 47,0 guanidin 0,05 56,0 0.1 0,2 94,0 N-Amyl-N'-phenyl-guani- 0.025 33.0 din 0,05 65,0 0,1 66,0 0,2 94,0 N-Äthyl-N'-m-Chlorphenyl- 0.025 67.0 guanidinhydrochlorid 0,05 78,0 0,1 92,0 0.2 93.0 9 Karathan (Etalon) 0.025 93.0 0,05 9o,0 Krankheitsentwicklung in der Probe 75%.Table 7 Serial Concentration Disease No preparation% control 1 2 3 4 1 N-methyl-N-propyl-N'-0.025 86.0 -m-chlorophenylguanidine 0.05 92.0 0.1 98.0 0.2 100.0 2 N -methyl-N-propyl-N'-m-0.025 82.0 trifluoromethylphenyl-0.05 91.0 guanidine 0.1 98.0 0.2 100.0 3 N-methyl-N-isopropyl-0.025 57.0 N'-m-chlorophenylguani- 0.05 70.0 din 0.1 87.0 0.2 100.0 4 N-methyl-N-butyl-N'-m-0.025 85.0 -chlorophenylguanidine 0.05 93.0 0.1 98.0 0.2 100.0 5 N-methyl-N-butyl-N'-p-0.025 45.0 -nitrophenylguanidine 0.05 59.0 0.1 82.0 0.2 90.0 6 Karathan (Etalon) 0.025 93.0 0.05 98.0 Disease development i in the sample 87.0%. - Table 8 Serial Concentration Disease No. Preparation% control% 1 2 3 4 1 N-methyl-N'-phenyl-0.025 44.0 guanidine 0.05 52.0 0.1 80.0 0.2 93.0 2 N -ethyl-N'-phenyl-0.025 45.0 guanidine 0.05 53.0 0.1 78.0 0.2 88.0 N-isopropyl-N'-phenyl-0.025 34.0 guanidine 0.05 59.0 0.1 79.0 0.2 81.0 4, N-isobutyl-N'-phenyl 0.025 43.0 guanidine 0.05 47.0 0.1 75.0 0.2 84.0 5 N-sec-Butyl-N'-phenyl-O.025 49.0 guanidine # 0.05 59.0 0.1 77.0 0.2 82.0 2 3 4 6 N-tert -butyl-N'-phenyl-0.025 47.0 guanidine 0.05 56.0 0.1 0.2 94.0 N-amyl-N'-phenyl-guani- 0.025 33.0 din 0.05 65.0 0.1 66.0 0.2 94.0 N-ethyl-N'-m -chlorophenyl-0.025 67.0 guanidine hydrochloride 0.05 78.0 0.1 92.0 0.2 93.0 9 Karathan (Etalon) 0.025 93.0 0.05 9o, 0 Disease development in the sample 75%.

Tabelle 9 Lfd. Konzentra- Beschädi- Krankheits- Nr. Präparate tion % gung der entwicklung Triebe % 1 N,N-Dimethyl-N'-m- 0.15 8.0 4.0 chlorphenylguanidin 2 benetzbarer Schwefel 0.45 10.0 5.0 (Etalon) 3 Probe - 16.0 13.0 Tabelle 10 Lfd. Konzentra- Krankheitsbe- Nr. Präparate tion % kämpfung % 1 N,N-Dimethyl-N'-m-chlor- phenylguanidin 0.25 95.0 2 N,N-Dimethyl-N'-3,4- dichlorphenylguanidin 0,25 72,0 3 N,N-Dimethyl-N'-m-nitro- phenylguanidin 0,25 94,0 4 N,N-Dimethyl-N'-p-nitro- phenylguanidin 0,25 94,0 5 N,N-Dimethyl-N'-3-chlor- 4-nitrophenylguanidin 0,25 @ 92,0 6 N,N-Dimethyl-N -4-chlor- -3-nitrophenylguanidin 0,25 96,0 7 N,N-Dimethyl-N'-3-nitro- 4-methylphenylguanidin 0,25 89,0 8 N,N-Dimethyl-N'-p-methoxy- phenylguanidin 0,25 79,0 9 N,N-Diisoprophyl-N'- phenylguanidin 0,25 83,0 10 Captan (Etalon) # 0,25 97,0 Mittlere Anzahl von Nekrosen in der Probe 37.Table 9 Serial Concentration Damage Disease No preparation of the development Shoots% 1 N, N-dimethyl-N'-m-0.15 8.0 4.0 chlorphenylguanidine 2 wettable sulfur 0.45 10.0 5.0 (Standard) 3 sample - 16.0 13.0 Table 10 Serial Concentration Disease No. preparation% fighting% 1 N, N-dimethyl-N'-m-chloro- phenylguanidine 0.25 95.0 2 N, N-dimethyl-N'-3,4- dichlorophenylguanidine 0.25 72.0 3 N, N-dimethyl-N'-m-nitro- phenylguanidine 0.25 94.0 4 N, N-dimethyl-N'-p-nitro- phenylguanidine 0.25 94.0 5 N, N-dimethyl-N'-3-chloro- 4-nitrophenylguanidine 0.25 @ 92.0 6 N, N-dimethyl-N -4-chloro- -3-nitrophenylguanidine 0.25 96.0 7 N, N-dimethyl-N'-3-nitro- 4-methylphenylguanidine 0.25 89.0 8 N, N-dimethyl-N'-p-methoxy- phenylguanidine 0.25 79.0 9 N, N-diisoprophyl-N'- phenylguanidine 0.25 83.0 10 Captan (Etalon) # 0.25 97.0 Mean number of necroses in sample 37.

Tabelle 11 Lfd. Konzentra- Krankheitsbe- Nr. Präparate tion % kämpfung % 1 Dimethyldithiokarbamat des N,N-Dimethyl-N'-m- -chlorphenylguanidine 0.25 89.0 2 Captan (Etalon) 0.25 91.0 Anzahl von Nekrosen in der Probe 69.Table 11 Serial Concentration Disease No. preparation% fighting% 1 dimethyl dithiocarbamate des N, N-dimethyl-N'-m- -chlorphenylguanidine 0.25 89.0 2 Captan (Etalon) 0.25 91.0 Number of necroses in the sample 69.

Tabelle 12 Lfd. Konzentra- Krankheitsbe- Nr. Präparate tion % kämpfung % 1 methylsulfat des N,N-Di- methyl-N'-phenylguani- dins 0,25 64,0 2 Captan (Etalon) 0.25 77.0 Anzahl von Nekrosen in der Probe 153.Table 12 Serial Concentration Disease No. preparation% fighting% 1 methyl sulfate of the N, N-Di- methyl-N'-phenylguani- dins 0.25 64.0 2 Captan (Etalon) 0.25 77.0 Number of necroses in the sample 153.

Tabelle 13 Lfd. Konzentra- Krankheitsbe- Nr. Präparate tion % kämpfung % 1 N,N-Dipropyl-N '-phenyl- guanidin 0.25 75.0 2 N,N-Dipropyl-N'-p-chlor- phenylguanidin O,25 75,0 3 N,N-Dipropyl-N-p-brom- phenylguanidin 0.25 4 Captan (Etalon) 0,25 92,0 Anzahl von Nekrosen in der Probe 100.Table 13 Serial Concentration Disease No. preparation% fighting% 1 N, N-dipropyl-N '-phenyl- guanidine 0.25 75.0 2 N, N-dipropyl-N'-p-chloro- phenylguanidine 0.25 75.0 3 N, N-dipropyl-Np-bromo- phenylguanidine 0.25 4 Captan (Etalon) 0.25 92.0 Number of necroses in the sample 100.

'l'abelle 14 Lfd. Lonzentra- Krankheitsbe- Nr. Präparate tion % kämpfung 73 1 N-Methyl-N-äthyl-N'-p- chlorphenylguanidin 0,25 83,0 2 N-Methyl-N-äthyl-N'-p- bromphenylguanidin 0,25 81,0 3 Captan (Etalon) 0.25 97.0 Anzahl von Nekrosen in der Probe 40.'l'abelle 14 Serial Lonzentra disease No. Preparation% fighting 73 1 N-methyl-N-ethyl-N'-p- chlorophenylguanidine 0.25 83.0 2 N-methyl-N-ethyl-N'-p- bromophenylguanidine 0.25 81.0 3 Captan (Etalon) 0.25 97.0 Number of necroses in the sample 40.

Tabelle 15 Lfd. Konzentra- Krankheitsbe- Nr. Präparate tion kämpfung % 1 N-Methyl-N-propyl-N'-m- trifluormethylphenylgua- nidin 0,25 65,0- -2 taptan (Etalon) 0,25 # 75,0 Anzahl von Nekrosen in der Probe 72.Table 15 Serial Concentration Disease No. Preparation fighting% 1 N-methyl-N-propyl-N'-m- trifluoromethylphenylgua- nidin 0.25 65.0- -2 taptan (etalon) 0.25 # 75.0 Number of necroses in the specimen 72.

Tabelle 16 Lfd. Konzentra- Krankheitsbe- Nr. Präparate tion % kämpfung % 1 N-Methyl-N'-phenylguani- din 0,25 96,0 2 N-tert-Butyl-N'-phenyl- guanidin 0,25 95,0 3 N-Amyl-N'-phenylguani- din 0,25 bs,0 4 Captan (Etalon) 0,25 97,0 Anzahl der Nekrosen in der Probe 39.Table 16 Serial Concentration Disease No. preparation% fighting% 1 N-methyl-N'-phenylguani- din 0.25 96.0 2 N-tert-butyl-N'-phenyl- guanidine 0.25 95.0 3 N-amyl-N'-phenylguani- din 0.25 bs, 0 4 Captan (Etalon) 0.25 97.0 Number of necroses in specimen 39.

Claims (1)

Patentansprüche Claims 1. Fungizide Mittel auf der Basis von N,N-di-(bzw.-mono)-alkyl--N1-aryl-substituierten Guanidinen in Form von freien Basen bzw. Salzen zur Bekämpfung von Mehltaupilzen und Grauschimmel an Pflanzen, enthaltend als Wirkstoff Verbindungen der allgemeinen Formeln a) für freie Basen: worin R - H, CH3, 02H5', n-C3H7 oder i-C3H7; R' - OH3, C2H5, n-C3H7, i-C3H7, n-C4H9, i-C4H9, tert-C4H9 oder C5H11 und x, y, z - H, Cl, Br, CH3, CH3O, N02 oder CF3 bedeuten; b) für Salze: worin R, R', x, y und z-analog den oben erwahnten Substituenden, B-der Säurerest Cl', CH3SO4', (CH3)2NCSS', S4O6" oder C6H2(N02)30' bedeuten.1. Fungicidal agents based on N, N-di- (or -mono) -alkyl-N1-aryl-substituted guanidines in the form of free bases or salts for combating powdery mildew and gray mold on plants, containing as active ingredient Compounds of the general formulas a) for free bases: wherein R - H, CH3, 02H5 ', n-C3H7 or i-C3H7; R '- OH3, C2H5, n-C3H7, i-C3H7, n-C4H9, i-C4H9, tert-C4H9 or C5H11 and x, y, z - H, Cl, Br, CH3, CH3O, NO2 or CF3; b) for salts: where R, R ', x, y and z-analogously to the above-mentioned substituents, B-denote the acid radical Cl', CH3SO4 ', (CH3) 2NCSS', S4O6 "or C6H2 (NO2) 30 '. 2. Fungizide Mittel nach Anspruch 1, enthaltend als Wirkstoff N,N-Dimethyl-N'-m-chlorphenyl-guanidin, N,N-Dimethyl-N'-p--bromphenylguanidin, N,N-Dimethyl-N'-m-trifluormethylphenylguanidin, N,N-Dimethyl-N'-m-nitrophenylguanidin oder N,N--Dimethyl-N'-3-chlor-4-nitrophenylguanidin.2. Fungicidal agents according to claim 1, containing as active ingredient N, N-dimethyl-N'-m-chlorophenyl-guanidine, N, N-dimethyl-N'-p - bromophenylguanidine, N, N-dimethyl-N'-m-trifluoromethylphenylguanidine, N, N-dimethyl-N'-m-nitrophenylguanidine or N, N-dimethyl-N'-3-chloro-4-nitrophenylguanidine. 5. Fungizide Mittel nach Anspruch 1, enthaltend als Wirkstoff N-Methyl-N-äthyl-N'-m-chlorphenylguanidin, N-Methyl-N--äthyl-N'-3,4-dichlorphenylguanidin, N-Methyl-N-propyl-N'--m-chlorphenylguanidin, N-Methyl-N-butyl-N'-m-chlorphenylguanidin oder N-Methyl-N-propyl-N'-m-trifluormethylphenylguanidin.5. Fungicidal agents according to claim 1, containing as active ingredient N-methyl-N-ethyl-N'-m-chlorophenylguanidine, N-methyl-N - ethyl-N'-3,4-dichlorophenylguanidine, N-methyl-N-propyl-N '- m-chlorophenylguanidine, N-methyl-N-butyl-N'-m -chlorophenylguanidine or N-methyl-N-propyl-N'-m-trifluoromethylphenylguanidine. 4. Fungizide Mittel nach Anspruch 1, enthaltend als Wirkstoff die Dimethyldithiokarbamate von N,N-Dimethyl-N'-m-chlorphenylguanidin oder N,N-Dimethyl-N'-m-trifluormethylphenylguanidin oder das N,N-Dimethyl-N'-m-chlorphenylguanidintetrathionat.4. Fungicidal agents according to claim 1, containing the active ingredient Dimethyldithiocarbamates of N, N-dimethyl-N'-m-chlorophenylguanidine or N, N-dimethyl-N'-m-trifluoromethylphenylguanidine or the N, N-dimethyl-N'-m-chlorophenylguanidine tetrathionate. 5. Verwendung der fungiziden Mittel nach Anspruch 1 bis 4 in Form 20 bis 8/oiger benetzbarer Pulver.5. Use of the fungicidal agents according to claims 1 to 4 in the form 20 to 8% wettable powder. 6. Verwendung der fungiziden Mittel nach Anspruch 1 bis 4 in Form 2 bis 20%iger Ståbemittel.6. Use of the fungicidal agents according to claims 1 to 4 in the form 2 to 20% strength stabilizer. 7. Verwendung der fungiziden Mittel nach Anspruch 1 bis 4 in Form 20 bis 80%iger Emulsionskonzentrate.7. Use of the fungicidal agents according to claim 1 to 4 in the form 20 to 80% emulsion concentrates.
DE19712133056 1971-07-02 1971-07-02 Use of NJS-di-alkyl-N'aryl-substituted guanidines for combating powdery mildew and gray mold on plants Expired DE2133056C3 (en)

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EP0406699A2 (en) * 1989-07-06 1991-01-09 BASF Aktiengesellschaft Fungicidal guanidines
EP0517852A1 (en) * 1990-03-02 1992-12-16 STATE OF OREGON, acting through OREGON STATE BOARD OF HIGHER EDUCATION, acting for OREGON HEALTH SC. UNIV. AND UNIV. OF OREGON Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5336689A (en) * 1990-03-02 1994-08-09 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5385946A (en) * 1986-07-10 1995-01-31 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Method for treating hypertension with disubstituted granidine compounds
US5403861A (en) * 1991-02-08 1995-04-04 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
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US5559154A (en) * 1990-03-02 1996-09-24 Oregon State Board Of Higher Education Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5574070A (en) * 1990-05-25 1996-11-12 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5604228A (en) * 1986-07-10 1997-02-18 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5741661A (en) * 1991-02-08 1998-04-21 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5847006A (en) * 1991-02-08 1998-12-08 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6143791A (en) * 1994-02-03 2000-11-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6147063A (en) * 1993-05-27 2000-11-14 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
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US5478863A (en) * 1986-07-10 1995-12-26 State Of Oregon, Oregon Health Sciences University Of Oregon Substituted guanidines having high binding to the sigma receptor and the use thereof
US5385946A (en) * 1986-07-10 1995-01-31 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Method for treating hypertension with disubstituted granidine compounds
US5604228A (en) * 1986-07-10 1997-02-18 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5126374A (en) * 1989-07-06 1992-06-30 Basf Aktiengesellschaft Fungicidal guanidines
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US5336689A (en) * 1990-03-02 1994-08-09 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
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US5559154A (en) * 1990-03-02 1996-09-24 Oregon State Board Of Higher Education Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5798390A (en) * 1990-03-02 1998-08-25 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5767162A (en) * 1990-03-02 1998-06-16 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US6251948B1 (en) 1990-03-02 2001-06-26 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5574070A (en) * 1990-05-25 1996-11-12 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5672608A (en) * 1991-02-08 1997-09-30 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US5686495A (en) * 1991-02-08 1997-11-11 Cambridge Neuroscience, Inc. Substituted hydrazinedicarboximidamides and methods of use thereof
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US5670519A (en) * 1991-02-08 1997-09-23 Cambridge Neuroscience, Inc. Acenaphthyl-substituted guanidines and methods of use thereof
US5622968A (en) * 1991-02-08 1997-04-22 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US5677348A (en) * 1991-02-08 1997-10-14 Cambridge Neuroscience, Inc. Substituted aminoguanidines and methods of use thereof
US5681861A (en) * 1991-02-08 1997-10-28 Cambridge Neuroscience, Inc. Aminoguanidines and methods of use of same
US6071969A (en) * 1991-02-08 2000-06-06 Cambridge Neuroscience, Inc. Substituted aminoguanidines and methods of use thereof
US5741661A (en) * 1991-02-08 1998-04-21 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5614630A (en) * 1991-02-08 1997-03-25 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US5403861A (en) * 1991-02-08 1995-04-04 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5837737A (en) * 1991-02-08 1998-11-17 Cambridge Neuroscience, Inc. Hydrazinedicarboximidamide compounds and pharmaceutical composition comprising same
US5847006A (en) * 1991-02-08 1998-12-08 Cambridge Neuroscience, Inc. Therapeutic guanidines
US5637623A (en) * 1991-02-08 1997-06-10 Cambridge Neuroscience, Inc. Substituted adamantyl guanidines and methods of use there of
US6153604A (en) * 1993-05-27 2000-11-28 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6147063A (en) * 1993-05-27 2000-11-14 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6013675A (en) * 1993-11-23 2000-01-11 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US5955507A (en) * 1993-11-23 1999-09-21 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US5922772A (en) * 1993-11-23 1999-07-13 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6156741A (en) * 1993-11-23 2000-12-05 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
WO1995014461A1 (en) * 1993-11-23 1995-06-01 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6143791A (en) * 1994-02-03 2000-11-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6174924B1 (en) 1994-02-03 2001-01-16 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6288123B1 (en) 1994-02-03 2001-09-11 Cambridge Neurosciences, Inc. Therapeutic guanidines
US6787569B1 (en) 1994-02-03 2004-09-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US7351743B1 (en) 1994-02-03 2008-04-01 Wyeth Therapeutic guanidines

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