DE1795772C3 - - Google Patents

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Publication number
DE1795772C3
DE1795772C3 DE19671795772 DE1795772A DE1795772C3 DE 1795772 C3 DE1795772 C3 DE 1795772C3 DE 19671795772 DE19671795772 DE 19671795772 DE 1795772 A DE1795772 A DE 1795772A DE 1795772 C3 DE1795772 C3 DE 1795772C3
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radical
protective
days
alkyl radical
compositions
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DE19671795772
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DE1795772A1 (en
DE1795772B2 (en
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Richard Stewart Elias
Peter Frank Hilary Freeman
Brian Kenneth Snell
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/69—Benzenesulfonamido-pyrimidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Description

Es wurde eine neue Gruppe von in 5- und 6-Stellung substituierten 2-Amino-4-hydroxypyrimidinderivaten aufgefunden, die sich durch eine außergewöhnlich fungizide Aktivität auszeichnen und zur Bekämpfung von Pilzerkrankungen an Pflanzen verwendet werden können.A new group of 2-amino-4-hydroxypyrimidine derivatives substituted in the 5- and 6-positions has been created found, which are characterized by an extraordinary fungicidal activity and to control of fungal diseases on plants can be used.

Die Erfindung betrifft 2-Amino-4-hydroxypyrimidinderivate der allgemeinen Formel IThe invention relates to 2-amino-4-hydroxypyrimidine derivatives of the general formula I.

bung und den Ansprüchen mit der folgenden Formel bezeichnet:exercise and claims with the following formula:

OHOH

Die Verbindungen können jedoch auch mit tautomeren Strukturformeln, z. B. (IV) oder (V), dargestellt werden.However, the compounds can also have tautomeric structural formulas, e.g. B. (IV) or (V) shown will.

R4 R 4

in der entweder Ri einen niederen Alkylrest und R2 einen Alkylrest mit 2 bis 4 Kohlenstoffatomen oder einen Allylrest bedeutet; oder Ri und R2 zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen Pyrrolidino- oder Piperidinorest bedeuten; R3 einen niederen Alkylrest und R-. einen niederen Alkylrest oder einen Allylrest bedeutet, sowie deren Salze.in which either Ri is a lower alkyl radical and R2 is an alkyl radical having 2 to 4 carbon atoms or an allyl radical; or Ri and R 2 together with the nitrogen atom to which they are attached represent a pyrrolidino or piperidino radical; R 3 is a lower alkyl radical and R-. denotes a lower alkyl radical or an allyl radical, as well as their salts.

In dieser Beschreibung ist die Numerierung des Pyrimidinrings wie folgt:In this description, the numbering of the pyrimidine ring is as follows:

oderor

RM Γ0 N NH R M Γ 0 N NH

τ !τ !

/ \
R1 R2 / \
R 1 R 2

R4R4

HN NHN N

(IV(IV

Es wird darauf hingewiesen, daß die A- und die 6-Stellung äquivalent sind.It should be noted that the A and 6 positions are equivalent.

Die erfindungsgemäßen Pyrimidinderivate werden der Zweckmäßigkeit halber in der gesamten Beschrei-The pyrimidine derivatives according to the invention are for the sake of convenience in the entire description

/ \
R, R2 / \
R, R 2

Die Erfindung umfaß auch die tautomeren Formen.The invention also encompasses the tautomeric forms.

Die Salze der erfindungsgemäßen Pyrimidinderivate sind vorzugsweise Alkalimetallsalze oder Hydrohalogenide, insbesondere Hydrochloride.The salts of the pyrimidine derivatives according to the invention are preferably alkali metal salts or hydrohalides, especially hydrochloride.

Spezielle Beispiele von erfindungsgemäßen Verbindungen sind in der folgenden Tabelle i aufgeführt.Specific examples of compounds according to the invention are listed in Table i below.

rabelle Itable I 33 /
—N /
—N C2H5 C 2 H 5 1717th R1 R 1 95 77295 772 44th Verbindung
Nr.link
No. NR1R,NR 1 R, CH,CH, CH,CH, R4R4 Physikalische
EigenschaftenPhysical
properties 11 -α-α CH,CH, n-C4H9 nC 4 H 9 Fp. 149'CM.p. 149'C 22 — N(n-C4H9)2 - N (nC 4 H 9 ) 2 CH,CH, n-C4H9 nC 4 H 9 Fp. 145—148° CM.p. 145-148 ° C 33 —N^~\—N ^ ~ \ n-C4H9 nC 4 H 9 Fp. 126iJCMp. 126 iJ C CH,CH, CH,CH, 44th n-C4H9 nC 4 H 9 Fp. lOrCFp. LOrC

55 — Ν
\- Ν
\ H5 H 5 CH3 CH 3 n-C,H7 nC, H 7 Fp.Fp. 116—117°116-117 ° CC. \
C2 \
C 2 5)25) 2 66th -N(C2H,-N (C 2 H, CH,CH, n-C,H7 nC, H 7 Fp.Fp. 114—115114-115 CC. 77th N(C2H5),N (C 2 H 5 ), CH,CH, C2H5 C 2 H 5 Fp.Fp. 121—122C 121-122 C CC. 88th N(C2H5J2 N (C 2 H 5 J 2 CH,CH, -CH,- CH=CH2 -CH, -CH = CH 2 Fp.Fp. 110—111°110-111 ° CC.

Die erfindungsgemäßen Verbindungen besitzen eine Aktivität gegenüber einer großen Reihe von Pilzerkrankungen wie z. B. die folgenden:The compounds according to the invention have activity against a large number of fungal diseases such as B. the following:

Puccinia recondita (brauner Rost) an Weizen
Phytophthora infestans (späte Trockenfäule)Puccinia recondita (brown rust) on wheat
Phytophthora infestans (late blight)

an Tomaten
Sphaerotheca fuliginea (pulvriger Mehltau)on tomatoes
Sphaerotheca fuliginea (powdery mildew)

an Gurken
Erysiphe graminis (pulvriger Mehltau)of cucumbers
Erysiphe graminis (powdery mildew)

an Weizen und Gerste
Podosphaera leucotricha (pulvriger Mehltau)on wheat and barley
Podosphaera leucotricha (powdery mildew)

an Äpfeln
Uncinula necator (pulvriger Mehltau)on apples
Uncinula necator (powdery mildew)

an Rebstöcken
Plasmopara viticola (pulvriger Mehltau)on vines
Plasmopara viticola (powdery mildew)

an Rebstöckenon vines

Piricularia cryzae (Brand) an Reis
Venturia inaequalis (Schorf) an Äpfeln
Pythium ultimum an Erbsen
Fusarium culmorum an WeizenPiricularia cryzae (fire) on rice
Venturia inaequalis (scab) on apples
Pythium ultimum on peas
Fusarium culmorum on wheat

Ein besonders günstiges Merkmal der Aktivität der oben angegebenen Pyrimidinderivate ist ihr systematischer Effekt, d. h. ihr Vermögen, durch die Pflanze zu wandern und dadurch jeden Teil derselben, der einem Pilzbefall unterliegt, zu erreichen und den Befall zu bekämpfen.A particularly favorable feature of the activity of the above pyrimidine derivatives is their more systematic Effect, d. H. their ability to wander through the plant and thereby every part of it that belongs to one Fungal infestation is subject to reaching and fighting the infestation.

Die erfindungsgemäßen Verbindungen können in fungizide Zusammensetzungen formuliert werden, welche neben einem Pyrimidinderivat der allgemeinen Formel 1 auch übliche Hilfsstofie und Trägermittel enthalten.The compounds of the invention can be formulated into fungicidal compositions, which in addition to a pyrimidine derivative of the general formula 1, there are also customary auxiliaries and carriers contain.

Die Zusammensetzungen können für landwirtschaftliche und für gartenbauliche Zwecke verwendet werden, und die Type der verwendeten Zusammensetzung hängt in jedem Fall vom jeweiligen Zweck ab, für den sie VcTwcriuci WcTucn SCn.The compositions can be used for agricultural and for horticultural purposes, and the type of composition used depends in each case on the particular purpose for which it is used VcTwcriuci WcTucn SCn.

Die Zusammensetzungen können die Form von Bestäubungspulvern oder Granalien aufweisen, wobei der aktive Bestandteil mit einem festen Trägermittel gemischt wird. Geeignete feste Trägermittel sind z. B. Kaolin, Bentonit, Kieselgur, Dolomit, Calciumcarbonat, Talkum, pulverisierte Magnesia, Fullersche Erde, Gips, Hewittsche Erde, Diatomeenerde und Porzellanerde. Zusammensetzungen für die Saatbeizung können beispielsweise ein Mittel enthalten, das die Haftung der Zusammensetzung am Samen erhöht, wie z. B. ein Mineralöl.The compositions may be in the form of dusting powders or granules, wherein the active ingredient is mixed with a solid carrier. Suitable solid carriers are e.g. B. Kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum, Hewitt's earth, diatomaceous earth, and china clay. Compositions for seed dressing can for example contain an agent which increases the adhesion of the composition to the seed, e.g. B. a Mineral oil.

Die Zusammensetzungen können auch die Form von dispergierbaren Pulver oder Körnern aufweisen, die zusätzlich zum aktiven Bestandteil ein Netzmittel enthalten, um die Dispergierung des Pulvers oder der Körner in Flüssigkeiten zu erleichtern. Solche Pulver oder Körner können Füllstoffe, Suspendiermittel oder ähnliches enthalten.The compositions may also take the form of dispersible powders or granules, the In addition to the active ingredient, contain a wetting agent to ensure the dispersion of the powder or the To facilitate grains in liquids. Such powders or granules can contain fillers, suspending agents or similar included.

Die Zusammensetzungen können auch die Form von flüssigen Präparaten aufweisen, die als Tauchmittel oder Spritzmittel verwendet werden können, wobei es sich im allgemeinen um wäßrige Dispersionen oder Emulsionen handelt, die den aktiven Bestandteil in Gegenwart ein oder mehrerer Netzmittel, Dispergiermittel, Emulgiermittel oder Suspendiermittel enthalten. Die wäßrigen Dispersionen oder Emulsionen können dadurch hergestellt werden, daß man den aktiven Bestandteil oder die aktiven Bestandteile in einem organischen Lösungsmittel auflöst, welches ein oder mehrere Netzmittel, Dispergiermittel oder Emulgiermittel enthalten kann, worauf man das so erhaltene Gemisch in Wasser gibt, welches gleichfalls ein oder mehrere Netzmittel, Dispergiermittel oder Emulgiermittel enthalten kann. Geeignete organische Lösungsmittel sind Älhylendichlorid, Isopropylalkohol, Propylenglykol, Diacetonalkohol, Toluol, Kerosin, Methylnaphthalin, Xylole und Trichlorethylen.The compositions may also be in the form of liquid preparations used as dipping agents or Spray compositions can be used, which are generally aqueous dispersions or emulsions acts that the active ingredient in the presence of one or more wetting agents, dispersants, emulsifiers or contain suspending agents. The aqueous dispersions or emulsions can thereby can be prepared that the active ingredient or ingredients in an organic Dissolves solvents which contain one or more wetting agents, dispersants or emulsifiers can, whereupon the mixture thus obtained is in water, which is also one or more May contain wetting agents, dispersants or emulsifiers. Suitable organic solvents are Ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, Xylenes and trichlorethylene.

Die als Spritzmittel zu verwendenden Zusammensetzungen können auch die Form von Aerosolen aufweisen, worin der Ansatz in einem Behälter unter Druck gehalten wird, in welcher ein Treibmittel, wie z. B. Fluortrichlormethan oder Dichlordifluormethan, anwesend ist.The compositions to be used as sprays can also be in the form of aerosols have, wherein the batch is kept under pressure in a container in which a propellant such as z. B. fluorotrichloromethane or dichlorodifluoromethane, is present.

Durch die Einarbeitung von geeigneten Zusätzen, wie z. B. für eine Verbesserung der Verteilung, der Haftfähigkeit und der Widerstandsfähigkeit gegen Regen an behandelten Oberflächen, können die einzelnen Zusammensetzungen besser für die verschiedensten Verwendungen, für die sie beabsichtigt sind, geeignet gemacht werden.By incorporating suitable additives, such as. B. for an improvement in the distribution, the Adhesion and resistance to rain on treated surfaces, the individual compositions better for the various uses for which they are intended, be made suitable.

Erfindungsgemäße Zusammensetzungen wurden in der folgenden Weise hergestellt und gegen die verschiedensten Pilzerkrankungen getestet; die Ergebnisse dieser Tests sind in der folgenden Tabelle Il angegeben. In den Tests wurde wowohl die schützende als auch die abtötende Aktivität untersucht. Bei den Tests auf schützende Aktivität wurden die Pflanzen bespritzt, so daß die Blätter mit einer Lösung oder einer Suspension benetzt waren, die 500 ppm der aktiven Verbindung und 0,1% Netzmittel enthielt, worauf sie nach 24 st mit der betreffenden Krankzeit geimpft wurden. Das Ausmaß der Krankheit wurde am Ende des Tests visuell bestimmt. Bei den Tests auf abtötende Aktivität wurden die Pflanzen mit der betreffenden Krankheit geimpft und nach einer Anzahl von Tagen, die von der Krankheit abhing, mit einer Lösung oder Suspension bespritzt (so daß die Blätter benetzt waren), welche 500 ppm aktive Verbindung und 0,1% Netzmittel enthielt. Die Ergebnisse sind in der Tabelle Il angegeben, wobei eine Einstufung gewählt wurde, die das prozentuale Ausmaß der Krankheit angab.Compositions of the present invention were prepared and tested against in the following manner various fungal diseases tested; the results of these tests are given in Table II below specified. Both the protective and the killing activity were examined in the tests. Both Tests for protective activity were sprayed on the plants, leaving the leaves with a solution or a Suspension containing 500 ppm of the active compound and 0.1% wetting agent, whereupon they were vaccinated after 24 hours with the relevant sick leave period. The extent of the disease was at the end of the Tests determined visually. In the tests for killing activity, the plants were infected with the relevant Vaccinated disease and after a number of days depending on the disease with a solution or Splashed suspension (so that the leaves were wetted) containing 500 ppm active compound and 0.1% wetting agent contained. The results are given in Table II, a classification being chosen which indicated the percentage of the disease.

Einstufung Prozentuales Ausmaß
der KrankheitClassification as a percentage
illness

61 bis 10061 to 100

26 bis 6026 to 60

6 bis 256 to 25

Obis 5Obis 5

Tabelle IlTable Il PuCi. 11.1 !
(Rosl)PuCi. 11.1!
(Rosl) reconditarecondita Phylophthora
infcstans
(späte TrocKJiifiiule)Phylophthora
infcstans
(late TrocKJiifiiule) Sphaerothcca
fuligincu
(pulvriger Mehltau)Sphaerothcca
fuligincu
(powdery mildew) tötendkilling F.rysiphc graminis
(pulvriger Mehltau)F.rysiphc graminis
(powdery mildew) F.rysiphc graminis
(pulvriger Mehltau)F.rysiphc graminis
(powdery mildew) Verb.
Nr.Verb.
No. Weizen
IO Tagewheat
IO days Tomate
4 Tagetomato
4 days Gurke
10 Tagecucumber
10 days 33 Weizen
10 Tagewheat
10 days Gerste
IO Tagebarley
IO days schützendprotective tötendkilling schützend tötendprotective killing schützendprotective 33 schützend tötendprotective killing schützend tötendprotective killing üü 00 22 33 ■1■ 1 22 33 11 00 00 00 33 33 00 22 22 00 00 0 00 0 33 33 33 11 33 00 00 -- 33 33 33 33 44th 00 00 -- 33 33 33 33 55 33 00 -- 22 33 -- -- 66th 00 00 -- 33 -- 22 ■ι _■ ι _ 77th 11 11 33 33 33 88th 00 __ 00 33 00 00 DiazinonDiazinon

Tabelle Il (Fortsetzung)Table II (continued)

Verb.
Nr.Verb.
No. Podosphaera
leucotricha
(pulvriger Mehltau)Podosphaera
leucotricha
(powdery mildew) -- 00 Uncinula necator
(pulvriger Mehltau)Uncinula necator
(powdery mildew) Plasmopara viticola
(flaumiger Mehltau)Plasmopara viticola
(downy mildew) Piricularia cr>/ac
(Brand)Piricularia cr> / ac
(Fire) Venturia inaequalis
(Schorf)Venturia inaequalis
(Scab) Apfel
7-14 TageApple
7-14 days Rebstock
14 TageVine
14 days Rebstock
7 TageVine
7 days Reis
7 Tagerice
7 days Apfel
14 TageApple
14 days schützend tötendprotective killing schützend lötendprotective soldering schützend lötendprotective soldering schützend tötendprotective killing schützend tötendprotective killing 11 11 00 22 22 11 22 00 00 22 22 11 33 11 00 11 33 00 44th 33 33 11 I _I _ 00 SS. -- -- -- 00 (1(1 33 33 τ „τ " 33 -- 77th 11 00 00 00 00 XX tt ~) -~) - -- 00 DiazinonDiazinon 00 00 00 00

Die erfindungsgemäßen Verbindungen weisen nicht nur eine außergewöhnlich hohe fungicide Aktivität auf, sondern sie besitzen auch eine sehr niedrige Toxität gegenüber Warmblütern, insbesondere Säugern.The compounds according to the invention not only have an exceptionally high fungicidal activity, but they also have very low toxicity to warm-blooded animals, particularly mammals.

So wurde für das den erfindungsgemäßen Verbindungen strukturell nahe verwandte 2-Äthylamino-4-methyl-5-n-butyl-6-hydroxypyrimidin, das Gegenstand der parallelen Anmeldung P 17 95 726.544 ist, die folgenden akuten oralen LDm-Werte ermitteltFor example, 2-ethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidine, which is structurally closely related to the compounds according to the invention, which is the subject of the parallel application P 17 95 726,544, the following acute oral LDm values determined

TierartAnimal species

Akuter oraler LD50-WertAcute oral LD50

Ratte (weiblich)Rat (female)

Maus (weiblich)Mouse (female)

Ratte (männlich)Rat (male)

Meerschweinchen (weiblich)Guinea pig (female)

Katze (weiblich)Cat (female)

4000 mg/kg
4000 mg/kg
1000-2000 mg/kg
500-1000 mg/kg
größer als 1000 mg/kg
4000 mg/kg4000 mg / kg
4000 mg / kg
1000-2000 mg / kg
500-1000 mg / kg
greater than 1000 mg / kg
4000 mg / kg

Demgegenüber sind bei einer weiblichen Ratte die entsprechenden Werte für die handelsüblich bekannte Verbindung Diazinon (2-Isopropyl-4-methyl-6-hydroxypyrimidin-diäthoxythiophosphorsäureester) 110 mg/kg (unstabilisierte Verbindung) bzw. 300-850 mg/kg (stabilisierte Verbindung). Es ist darauf hinzuweisen, daß sich Diazinon sehr leicht in noch giftigere Produkte zersetzt Gegenüber Bienen ist die erfindungsgemäße Verbindung überhaupt nicht Diazinon dagegen sehr giftig. Dasselbe gilt für die aus der GB-PS 1019 227 bekannten Thiophosphorsäureester bestimmter 2-Amino-4-hydroxypyrimidine, die den erfindungsgemäßen Verbindungen strukturell ähnlich sind. Eine Wirkung aufIn contrast, the values for a female rat are those that are commercially known Compound Diazinon (2-isopropyl-4-methyl-6-hydroxypyrimidine diethoxythiophosphoric acid ester) 110 mg / kg (unstabilized compound) or 300-850 mg / kg (stabilized Link). It should be noted that diazinon is very easily converted into even more toxic products decomposed Compared to bees, the compound according to the invention is not at all diazinon, on the other hand very much poisonous. The same applies to those from GB-PS 1019 227 known thiophosphoric acid esters of certain 2-amino-4-hydroxypyrimidines, which the invention Connections are structurally similar. An effect on

die Haut konnte bei den üblichen verdünnten Spritzmitteln nicht festgestellt werden. Auch eine Reizung der Augen tritt praktisch nicht auf.the skin could not be detected with the usual diluted spray agents. Also an irritation of the Eyes practically does not occur.

Die Herstellung der erfindungsgemäßen Verbindungen wird anhand des folgenden Beispiels näher erläutert.The preparation of the compounds according to the invention is illustrated in more detail by means of the following example explained.

Beispielexample

Die Verbindung 5-n-Butyl-4-hydroxy-6-methyl-2-pyrrolidino-pyrimidin der FormelThe compound 5-n-butyl-4-hydroxy-6-methyl-2-pyrrolidino-pyrimidine the formula

n-C4Hq nC 4 H q

wurde wie folgt hergestellt:was made as follows:

Ein Gemisch aus 5-n-Butyl-4-hydroxy-6-rnethyl-2-methylthiopyrimidin (10,6 g, 0,05 MoI) und PyrrolidinA mixture of 5-n-butyl-4-hydroxy-6-methyl-2-methylthiopyrimidine (10.6 g, 0.05 mol) and pyrrolidine

?-, (17,75 g, 0,025 Mol) in Cellosolve (30 ml) wurdel 6 st auf Rückfluß gehalten. Beim Abkühlen schied sich das Produkt aus und wurde aus Cellosolve umkristallisiert, wobei farblose Nadeln mit einem Fp. von 149° C erhalten wurden (9,8 g, 83%).? -, (17.75 g, 0.025 mol) in Cellosolve (30 ml) was added for 6 st Held at reflux. On cooling, the product separated out and was recrystallized from Cellosolve, colorless needles with a melting point of 149 ° C. were obtained (9.8 g, 83%).

in Die übrigen in Tabelle I oben bezeichneten Verbindungen wurden ebenfalls nach dem vorhergehenden Verfahren unter Verwendung der entsprechenden Reaktionsstoffe hergestellt.in The remainder identified in Table I above Connections were also made according to the previous procedure using the appropriate Reaction substances produced.

Claims (1)

Patentansprüche: In 5- und 6-Stellung substituierte 2-Amino-4-hydroxypyrimidinderivate der allgemeinen Formel IClaims: 2-Amino-4-hydroxypyrimidine derivatives of the general formula I substituted in the 5- and 6-positions OHOH in der entweder Ri einen niederen Alkylrest und R2 einen Alkylrest mit 2 bis 4 Kohlenstoffatomen oder einen AJlylrest bedeutet; oder Rj und R2 zusammen mit dem Stickstoffatom, an das sie gebunden sind.in which either Ri is a lower alkyl radical and R2 is an alkyl radical having 2 to 4 carbon atoms or an AJlyl radical; or Rj and R 2 together with the nitrogen atom to which they are attached. einen Pyrrolidino- oder Piperidinorest bedeuten; R3 einen niederen Alkylrest und R4 einen niederen Alkylrest oder einen Allylrest bedeutet, sowie deren Salze.denote a pyrrolidino or piperidino radical; R3 is a lower alkyl radical and R4 is a lower one Denotes an alkyl radical or an allyl radical, as well as their salts.
DE19671795772 1966-03-31 1967-03-23 2-AMINO-4-HYDROXYPYRIMIDINE DERIVATIVES SUBSTITUTED IN THE 5- AND 6-POSITION Granted DE1795772B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1427166A GB1182584A (en) 1966-03-31 1966-03-31 Pyrimidine derivates and the use thereof as fungicides
GB1427167 1967-02-24

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DE1795772A1 DE1795772A1 (en) 1975-09-04
DE1795772B2 DE1795772B2 (en) 1977-11-10
DE1795772C3 true DE1795772C3 (en) 1978-06-29

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ID=26250433

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DE19671795726 Expired DE1795726C3 (en) 1966-03-31 1967-03-23 2-amino-4-methyl-5-alkyl-6-hydroxy-. pyridine derivatives
DE19671795772 Granted DE1795772B2 (en) 1966-03-31 1967-03-23 2-AMINO-4-HYDROXYPYRIMIDINE DERIVATIVES SUBSTITUTED IN THE 5- AND 6-POSITION
DE19671795833 Expired DE1795833C3 (en) 1966-03-31 1967-03-23 2-Amino-6-hydroxypyrimidine derivatives substituted in the 5-position
DE19671795835 Expired DE1795835C3 (en) 1966-03-31 1967-03-23 2-Dimethylamino ^ -alkyl-e-hydroxy- or mercapto-pyrimidine derivatives substituted in the 5-position
DE1967J0033286 Granted DE1695270B2 (en) 1966-03-31 1967-03-23 AGENTS FOR CONTROLLING FUNGI IN PLANTS
DE19671795834 Pending DE1795834A1 (en) 1966-03-31 1967-03-23 FUNGICIDAL COMPOSITIONS AND METHOD FOR PREPARING THE SAME

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DE19671795726 Expired DE1795726C3 (en) 1966-03-31 1967-03-23 2-amino-4-methyl-5-alkyl-6-hydroxy-. pyridine derivatives

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Application Number Title Priority Date Filing Date
DE19671795833 Expired DE1795833C3 (en) 1966-03-31 1967-03-23 2-Amino-6-hydroxypyrimidine derivatives substituted in the 5-position
DE19671795835 Expired DE1795835C3 (en) 1966-03-31 1967-03-23 2-Dimethylamino ^ -alkyl-e-hydroxy- or mercapto-pyrimidine derivatives substituted in the 5-position
DE1967J0033286 Granted DE1695270B2 (en) 1966-03-31 1967-03-23 AGENTS FOR CONTROLLING FUNGI IN PLANTS
DE19671795834 Pending DE1795834A1 (en) 1966-03-31 1967-03-23 FUNGICIDAL COMPOSITIONS AND METHOD FOR PREPARING THE SAME

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AT (3) AT286992B (en)
BE (1) BE696470A (en)
BR (1) BR6788228D0 (en)
CH (1) CH497836A (en)
CS (1) CS165324B2 (en)
CY (1) CY623A (en)
DE (6) DE1795726C3 (en)
DK (1) DK126593B (en)
ES (1) ES338694A1 (en)
GB (1) GB1182584A (en)
IL (1) IL27542A (en)
MY (1) MY7300287A (en)
NL (1) NL152855B (en)
PH (1) PH11586A (en)
SE (2) SE356874B (en)
YU (1) YU33661B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4029784A (en) * 1971-09-23 1977-06-14 Imperial Chemical Industries Limited Pyrimidine sulfamate fungicides
GB1523274A (en) 1974-08-05 1978-08-31 Ici Ltd Herbicidal compositions containing substituted pyrimidine
IT1153066B (en) * 1982-11-18 1987-01-14 Mentedison S P A HERBICIDE ACTIVITIES OF PIRIMIDIN-4-ONE
JPH0635450B2 (en) * 1984-03-16 1994-05-11 三井東圧化学株式会社 Thiocyanopyrimidine derivative, its production method and agricultural / horticultural fungicide
JPS6345269A (en) * 1986-04-28 1988-02-26 Mitsui Toatsu Chem Inc Dihalogen-substituted thiocyanopyrimidine derivative, production thereof and agricultural and horticultural fungicide
US6252076B1 (en) 1996-05-04 2001-06-26 Yuhan Corporation Process for preparation of pyrimidine derivatives
WO1998018784A1 (en) * 1996-10-29 1998-05-07 Yuhan Corporation Process for preparation of pyrimidine derivatives
IN188411B (en) 1997-03-27 2002-09-21 Yuhan Corp
WO1999031072A1 (en) * 1997-12-18 1999-06-24 E.I. Du Pont De Nemours And Company Cyclohexylamine arthropodicides and fungicides
KR100272471B1 (en) 1998-11-17 2000-11-15 김선진 Novel pyrimidine derivatives and processes for the preparation thereof
JP2010503642A (en) 2006-09-18 2010-02-04 ビーエーエスエフ ソシエタス・ヨーロピア Ternary pesticide mixture
BRPI0807012A2 (en) 2007-02-06 2014-04-22 Basf Se USE OF INSECTICIDES, METHOD OF REDUCING OR AVOIDING THE PHYTOTOXIC EFFECT OF FUNGICIDES, AND, AGENT.
EP2161259A1 (en) * 2008-09-03 2010-03-10 Bayer CropScience AG 4-Haloalkyl substituted Diaminopyrimidine
CN102461503B (en) * 2010-11-08 2013-08-14 陕西汤普森生物科技有限公司 Mandipropamid and ethirimol containing fungicides combination
WO2015036563A1 (en) 2013-09-16 2015-03-19 Bayer Pharma Aktiengesellschaft Disubstituted trifluormethyl pyrimidinones and use thereof as ccr2 antagonists

Also Published As

Publication number Publication date
CS165324B2 (en) 1975-12-22
AT279968B (en) 1970-03-25
DE1795726C3 (en) 1978-07-27
CY623A (en) 1971-12-08
GB1182584A (en) 1970-02-25
CH497836A (en) 1970-10-31
DK126593B (en) 1973-07-30
DE1795726A1 (en) 1975-07-31
AT286992B (en) 1971-01-11
BR6788228D0 (en) 1973-06-05
DE1795772A1 (en) 1975-09-04
PH11586A (en) 1978-03-31
DE1795772B2 (en) 1977-11-10
DE1795833B2 (en) 1977-08-25
DE1795834A1 (en) 1976-06-24
NL6704456A (en) 1967-10-02
YU33661B (en) 1977-12-31
SE405117B (en) 1978-11-20
MY7300287A (en) 1973-12-31
DE1795726B2 (en) 1977-09-01
BE696470A (en) 1967-10-02
NL152855B (en) 1977-04-15
DE1695270B2 (en) 1977-05-26
DE1695270A1 (en) 1972-04-20
ES338694A1 (en) 1968-07-01
DE1795833A1 (en) 1976-03-11
DE1795833C3 (en) 1978-04-13
SE356874B (en) 1973-06-12
DE1795835A1 (en) 1976-06-24
DE1795835C3 (en) 1978-04-13
YU63067A (en) 1977-06-30
DE1795835B2 (en) 1977-08-25
IL27542A (en) 1975-10-15
AT276854B (en) 1969-12-10

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