PL123432B1 - - Google Patents

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PL123432B1
PL123432B1 PL228213A PL22821380A PL123432B1 PL 123432 B1 PL123432 B1 PL 123432B1 PL 228213 A PL228213 A PL 228213A PL 22821380 A PL22821380 A PL 22821380A PL 123432 B1 PL123432 B1 PL 123432B1
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PL
Poland
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formula
methyl
group
naphthyl
cooch3
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PL228213A
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Polish (pl)
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PL228213A2 (en
PL123432B2 (en
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Basf Aktiengesellschaft
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Publication date
Priority claimed from DE19792948704 external-priority patent/DE2948704A1/en
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of PL228213A2 publication Critical patent/PL228213A2/xx
Publication of PL123432B2 publication Critical patent/PL123432B2/en
Publication of PL123432B1 publication Critical patent/PL123432B1/pl

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • A—HUMAN NECESSITIES
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms
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    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Description

Opis patentowy opublikowano: 15.05.1984 Twórcawynalazku Uprawniony z patentu: BASF Aktiengesellschaft, Ludwigshafen (Republika Federalna Niemiec) Srodek grzybobójczy Przedmiotem omawianego wynalazku jest srodek grzybobójczy zawierajacy jako substancje czynna nowe N-podstawione 2-metylonaftyloamidy.Wiadomo juz, ze etyleno-l,2-bis-ditiokarbaminian cynkowy, N-trichlorometylotioftalimid oraz N-trichlorometylotiotetrahydroftalimid stosuje sie jako srodki grzybobójcze w rolnictwie i ogrodnictwie. Wymienione zwiazki sa dobrymi srodkami do zwalczania chorób grzybowych, np.R. Wegier, „Chemie der Pflanzenschutz- und Schadlingsbekampfungsmitter, tom 2, strony 65-66 i 109 oraz tom 4, strony 139 i 191, Berlin/Heidelberg/Nowy Jork, (1970) i (1977). Jednakze te srodki grzybobójcze nie nadaja sie do stosowania po nastapieniu infekcji, a dzialanie ich przy uzyciu niskich stezen nie odpowiada wymaganiom praktyki.Stwierdzono, ze silne dzialanie grzybobójcze wykazuja nowe N-podstawione 2- metylonaftyloamidy o wzorze ogólnym 1, w którym R1 oznacza grupe o wzorze —CO—R3, przy czym R3 oznacza atom wodoru albo grupe alkoksylowa o 1-4 atomach wegla i dalej Rl oznacza grupe o wzorze —CH/OR4/—OR5, przy czym R4 i R5 niezaleznie od siebie oznaczaja ewentualnie podstawiona grupe alkilowa o 1-4 atomach wegla albo R4 i R5 razem oznaczaja grupe alkilenowa, który razem z grupa, do której jest podstawiona, tworzy ewentualnie podstawiony przez grupe alkilowa o 1-4 atomach wegla albo przez grupe arylowa 5- albo 6-czlonowy pierscien heterocykli¬ czny, zawierajacy 2 atomy tlenu, a R2 oznacza grupe alkilowa o 1-4 atomach wegla, która jest ewentualnie podstawiona atomem fluoru, chloru, bromu lub jodu albo grupa alkoksylowa o 1-4 atomach wegla, grupa alkilotio o 1-4 atomach wegla, grupa 1-imidazolilowa, 1-pirazoliowa, 1,2,4-triazol-l-ilowa albo grupa keto, dalej R2 oznacza grupe alkenylowa o 2-5 atomach wegla, grupe alkinylowa o 2-5 atomach wegla, cykloalkilowa o 3-7 atomach wegla, cykloalkenylowa o 4-7 atomach wegla, grupe alkoksylowa o 1-5 atomach wegla, ewentualnie podstawiona grupe fenylowa albo ewentualnie podstawiona grupe heteroarylowa, zas X oznacza atom wodoru, grupe metylowa, atom chloru lub bromu.We wzorze ogólnym 1 R2 oznacza korzystnie nierozgaleziona lub rozgaleziona grupe alkoksy¬ lowa o 1-5 atomach wegla, np. grupe taka jak metoksylowa,etoksylowa,n-propoksylowa,izopro- poksylowa, n-butoksylowa, izobutoksylowa, sec-butoksylowa, tert-butoksylowa, n-pentyloksylo- wa albo izopentyloksylowa, albo oznacza ewentualnie podstawiona przez atom fluoru, chloru, bromu lub jodu, przez grupe metoksylowa, etoksylowa, butoksylowa, metylotio, etylotio, 1- imidazolilowa, 1-pirazolilowa albo przez grupe 1,2,4-triazol-l-ilowa rozgaleziona albo nierozgale-9 123 432 ziona grupe alkilowa o 1-4 atomach wegla, np. grupe metylowa, etylowa, n-propylowa, izopropy¬ lowe, n-butylowa, izobutylowa, sec-butylowa albo tert-butylowa. R2 oznacza poza tym przykla¬ dowo grupe winylowa, l-propenylowa, 2-propenylowa, allilowa, etynylowa albo na przyklad oykliczna grupe alkilowa lub alkenylowa o 3-7 atomach wegla w pierscieniu, na przyklad grupe cyklopropylowa, cyklopentylowa, cykloheksylowa albo cykloheksen-2-ylowa, poza tym przykla¬ dowo ewentualnie podstawiona grupe fenylowa albo ewentualnie podstawiona grupe heteroary- lowa o 5-6 atomach w pierscieniu w tym 1-3, zwlaszcza 1-2 jednakowych albo róznych heteroatomach takich jak zwlaszcza atom tlenu, azotu albo siarki, na przyklad grupe furanowa, tiofenowa, izoksazolowa albo pirydynowa.Wyrózniajacymi sie podstawnikami wymienionych wyzej jako R2 grup aromatycznych i heteroaromatycznych sa przykladowo atom chlorowca, zwlaszcza fluoru, chloru albo bromu; grupa nitrowa; prosta grupa alkilowa o 1-4 atomach wegla; grupa alkoksylowa lub alkilotio o 1-4 atomach wegla, np. grupa metoksylowa, etoksylowa albo grupa metylotio, etylotio lub n- propylotio; grupy chlorowcoalkilowa, chlorowcoalkoksylowa i chlorowcoalkilotio zawierajace do 4 atomów wegla i do 8 atomów chlorowca, zwlaszcza fluoru i chloru, na przyklad grupa trichloro- metylowa, trifluorometylowa lub tetrafluoroetoksylowa;grupacyjanowa,alkilokarbonylowaalbo alkoksykarbonylowa, na przyklad grupa metoksykarbonylowa, acetylowa lub propionylowa; ewentualnie podstawiona grupa fenylowa lub fenylokarbonylowa.R3 oznacza szczególnie atom wodoru oraz rozgaleziona lub nierozgaleziona grupe alkoksy¬ lowa o 1-4 atomach wegla, np. grupe metoksylowa, etoksylowa, n-propoksylowa, izopropoksy- lowa, n-butoksylowa, izobutoksylowa, sec-butoksylowa i tert-butoksylowa.R4 i R5 oznaczaja przykladowo ewentualnie podstawiona nierozgaleziona tub rozgaleziona grupe alkilowa, zawierajaca do 4 atomów wegla, na przyklad grupe metylowa, etylowa, n- propylowa, izopropylowa, n-butylowa albo izobutylowa. Poza tym R4 i R5 oznaczaja razem przykladowo grupe alkilenowa o 2 lub 3 atomach wegla, która jest ewentualnie podstawiona grupa alkilowa, zawierajaca do 4 atomów wegla, na przyklad grupa metylowa lub etylowa.X oznacza przewaznie atom wodoru, grupe metylowa, atom chloru albo bromu.Nowe N-podstawione 2-metylonaftyloamidy o wzorze ogólnym 1 posiadaja chilarny atom wegla z atomem wodoru, grupa CH3, R1 oraz =N jako Ugandami i zaleznie od rodzaju R2, R3, R4 i R5 dalsze centra chilarnosci. Optycznie czyste enancjomery wzglednie diastereoizomery otrzymuje sie zwyklymi metodami. Omawiany wynalazek obejmuje sposób wytwarzania tych zwiazków zarówno w stanie czystym jak tez w postaci mieszanin. Jako srodki grzybobójcze skuteczne sa czyste enancjomery wzglednie jednolite diastereoizomery jak tez otrzymywane zwykle z syntezy mieszaniny.Poza tym stwierdzono, ze nowe zwiazki o wzorze ogólnym 1 wytwarza sie korzystnie w ten sposób, ze 2-metylonaftyloamine o wzorze ogólnym 2, w którym R1 oraz X maja podane wyzej znaczenia, poddaje sie reakcji z halogenkiem kwasowym o wzorze ogólnym R2—CO—Hal albo z bezwodnikiem kwasowym o wzorze ogólnym R2—CO—O—CO—R2, w których to wzorach R2ma wyzej podane znaczenie, a Hal oznacza atom chloru albo bromu, przy czym reakcje prowadzi sie w temperaturze —10-100°C, ewentualnie w obecnosci rozpuszczalnika albo rozcienczalnika, ewen¬ tualnie z dodatkiem nieorganicznej lub organicznej zasady i ewentualnie z dodatkiem katalizatora.Jako korzystne, obojetne wobec reagentów rozpuszczalniki lub rozcienczalniki stosuje sie np. alifatyczne lub aromatyczne weglowodory jak pentan, cykloheksan, eter naftowy, benzen, toluen albo ksyleny; chlorowcoweglowodory, np. chlorek metylenu, chloroform, 1,2-dichloroetan lub chlorobenzen; ketony jak aceton i metyloetyloketon; etery jak eter dwuetylowy, dwumetoksyetan, tetrahydrofuran albo dioksan; estry jak octan etylu; nitryle jak acetonitryl; sulfotlenki jak dimety- losulfotlenek albo odpowiednie mieszaniny.Odpowiednimi zasadami nieorganicznymi lub organicznymi, które stosuje sie w reakcji ewen¬ tualnie takze jako srodki wiazace kwas, sa przykladowo weglany metali alkalicznych i metali ziem alkalicznych jak wodoroweglan sodowy lub potasowy, weglan sodowy lub potasowy, weglan wapniowy; boranyjak boran sodowy; fosforany jak fosforan disodowy lub trisodowy albo fosforan dipotasowy lub tripotasowy albo aminy jak trietyloamina, N,N-dimetyloanilina, N,N- dimetylocykloheksyloamina, N-metylopiperydyna albo pirydyna. Mozna tu stosowac takze inne zwykle zasady.123432 3 Jako katalizatory wchodza w rachube przewaznie halogenki metali jak bromek sodowy albo jodek potasowy, azole jak imidazol lub 1,2,4-triazol albo pirydyny jak 4-dimetyloaminopirydyna.Reakcje sposobem wedlug wynalazku prowadzi sie przykladowo w temperaturze —10-+100°C, zwlaszcza w temperaturze 0-+40°C, pod cisnieniem normalnym albo zwiekszonym, w sposób agly albo periodyczny, ciagly albo periodyczny.Poza tym stwierdzono, ze zwiazki o wzorze ogólnym 1 wytwarza sie w ten sposób, ze z 2-metylonaftyloamidu o wzorze ogólnym la, w którym R2 oraz X maja wyzej podane znaczenia, a R4 i R5 niezaleznie od siebie oznaczaja ewentualnie podstawiona grupe alkilowa o 1-4 atomach wegla, przez odszczepienie R4 i R5 otrzymuje sie odpowiedni aldehyd albo przez reakcje zdiolem o wzorze HO—R4—R5—OH, w którym R4 i R5 razem oznaczaja grupe alkilenowa, otrzymuje sie odpowiedni acetal cykliczny, przy czym reakcje prowadzi sie ewentualnie w obecnosci rozcienczal¬ nika i ewentualnie z dodatkiem kwasowego katalizatora.Do wymienionych dioli naleza przykladowo 1,2-etanodiol, 1,2-propanodiol, 1,3-propanodiol, 2,3-butanodiol i 2,2-dimetylo-l,3-propanodiol. Odszczepienie R4 i R5 prowadzi sie przykladowo przez dzialanie katalitycznych ilosci silnych kwasów protonowych lub kwasów Lewis'a jak chloro¬ wodoru wzglednie kwasu solnego, bromowodoru, kwasu p-toluenosulfonowego, kwasu trifluo- rooctowego, kwasu trifluorometanosulfonowego, chlorku cynkowego, bromku cynkowego albo eteratu trifluorku borowego, w temperaturze od 0°C do temperatury wrzenia odszczepianych alkoholi R4—OH i R5—OH. Reakcje z 1,2- albo 1,3-diolem prowadzi sie przykladowo w ten sposób, ze z mieszaniny reakcyjnej usuwa sie alkohole R4—OH i R5—OH przez destylacje pod cisnieniem zmniejszonym albo atmosferycznym, albo za pomoca obojetnego gazu jak azotu lub argonu. Jako rozpuszczalniki lub rozcienczalniki odpowiednie sa tu wymienione wyzej ciecze albo woda, albo nawet 1,2- lub 1,3-diole przy stosowaniu ilosci stechiometrycznej albo w nadmiarze.Jako kwasowe katalizatory stosuje sie tu kwasy Lewis'a lub protonowe, na przyklad BF3, AlCh, lub ZnCU albo kwasy mineralne lub sulfonowe.Zwiazki o wzorze ogólnym 1 otrzymuje sie poza tym w ten sposób, ze 2-metylonaftyloamid o wzorze ogólnym Ib, w którym R1 oraz X maja wyzej podane znaczenia, a Hal oznacza atom chlorowca, zas R6 oznacza atom wodoru, grupe alkilowa o 1-3 atomach wegla, grupe alkenyIowa o 2-4 atomach wegla, grupe cykloalkilowa o 3-7 atomach wegla lub grupe alkoksylowa o 1-5 atomach wegla, poddaje sie reakcji z nukleofilowym zwiazkiem o wzorze ogólnym NuH, w którym Nu oznacza grupe alkoksylowa o 1-5 atomach wegla albo grupe alkilotio o 1-4 atomach wegla, albo grupe 1-imidazolilowa, 1-pirazolilowa albo grupe 1,2,4-triazol-1-ilowa, przy czym reakcje prowadzi sie ewentualnie w obecnosci rozpuszczalnika albo rozcienczalnika, ewentualnie w obec¬ nosci nieorganicznej lub organicznej zasady i ewentualnie z dodatkiem katalizatora, w temperatu¬ rze — 10-+J00°C.Dalsze zwiazki o wzorze ogólnym 1 wytwarza sie tak, ze zaleznie od funkcjonalnego rodzaju R1 i R2 prowadzi sie zwykle chemiczne reakcje nastepcze. 2-metylonaftyloaminy o wzorze ogólnym 2, stosowane jako substancje wyjsciowe do wytwa¬ rzania zwiazków o wzorze ogólnym 1, otrzymuje sie w ten sposób, ze 2-metylonaftyloamine o wzorze ogólnym 3, w którym X ma wyzej podane znaczenie, poddaje sie reakcji z estrem kwasu 2-chlorowcopropionowego o wzorze ogólnym CH3—CH(Hal)—COOCi—C4—Alkil, w którym Hal oznacza atom chloru albo bromu, albo z acetalem dialkilowym 2-chlorowcopropanalu o wzorze ogólnym CH3—CH(Hal)—CH(OR4)—OR5, w którym Hal oznacza atom chloru lub bromu, a R4 i R5 maja wyzej podane znaczenia, ewentualnie w obecnosci rozpuszczalnika lub rozcienczalnika, ewentualnie w obecnosci nieorganicznej lub organicznej zasady i ewentualnie z dodatkiem katalizatora, w temperaturze —10-+130°C.Do wyrózniajacych sie rozpuszczalników i rozcienczalników, do nieorganicznych lub organi¬ cznych zasad oraz do katalizatorów naleza wymienione wyzej zwiazki.Dalej stwierdzono, ze zwiazki o wzorze ogólnym 2 otrzymuje sie w ten sposób, ze 2- metylonaftyloamine o wzorze ogólnym 3 poddaje sie reakcji z estrem kwasu pirogronowego o wzorze ogólnym CH3—CO—COOCi—C4—Alkil albo z acetalem metyloglioksalu o wzorze ogól¬ nym CH3—CO—CH(OR4)—OR5, w którym R4 oraz R5 maja wyzej podane znaczenia, i otrzymana4 123432 jako produkt reakcji zasade Schiffa'a poddaje sie uwodornieniu, np. kompleksowymi wodorkami metali albo katalitycznie wodorem.Wytwarzanie zasady Schiffa prowadzi sie przykladowo w ten sposób, ze 1 mol 2- metylonaftyloaminy o wzorze ogólnym 3 poddaje sie reakcji z 0,9-1,5 mola estru kwasu pirogrono- wego o wzorze ogólnym CH3—CO—COOCj—C4—Alkil albo acetalu metyloglioksalu o wzorze ogólnym CH3—CO—CH(OR4)—OR5, przy czym reakcje prowadzi sie w rozpuszczalniku ewen¬ tualnie z dodatkiem kwasowego katalizatora i w temperaturze 40-200°C, zwlaszcza 50-120°C oddziela sie wode droga destylacji. Do reakcji korzystnie stosuje sie rozpuszczalniki obojetne w warunkach reakcji i jednoczesnie tworzace z woda mieszaniny azeotropowe. Jako rozpuszczalniki wchodza w rachube np. aromatyczne weglowodory, przykladowo benzen, toluen, etylobenzen, o-, m-, i p-ksylen, izopropylobenzen, lub metylonaftalen; alifatyczne lub cykloalifatyczne weglowo¬ dory, przykladowo heptan, nonan, pinan, frakcje benzyny o temperaturze wrzenia 70-190°C, cykloheksan, metylocykloheksan, dekalina, ligroina, 2,2,4-trimetylopentan, 2,2,3-trimetylopen- tan, 2,3,3-trimetylopentan, oktan oraz odpowiednie mieszaniny.Uwodornianie prowadzi sie zarówno droga redukcji kompleksowymi wodorkami jak wodor¬ kiem sodowo-borowym, jak tez przez katalityczne uwodornienie wodorem.Redukcje wodorkiem sodowo-borowym prowadzi sie na ogól w ten sposób, ze w rozpuszczal¬ niku, w temperaturze —20-+40°C 1 mol zasady Schiffa poddaje sie reakcji z 0,2-1 molem wodorku sodowo-borowego.Przy uwodornianiu katalitycznym, do mieszaniny reakcyjnej na poczatku i w czasie reakcji wprowadza sie takie ilosci wodoru, ze w temperaturze reakcji stale utrzymuje sie odpowiednie cisnienie, korzystnie 15-30MPa. Reakcje prowadzi sie na ogól w temperaturze 20-200°C, zwla¬ szcza 25-160°C, w sposób periodyczny albo ciagly.Do ustawienia odpowiedniego cisnienia stosuje sie ewentualnie takze obojetne gazy jak azot.Jako rozpuszczalniki lub rozcienczalniki dla obydwu wariantów uwodorniania nadaja sie szczególnie dobrze alkanole i cykloakanole, np. n-propanol, izopropanol, n-butanol, izobutanol, glikol, eter monoetylowy glikolu etylenowego, gliceryna, alkohol amylowy, cykloheksanol, 2- metylo-4-pentanol, 2-etyloheksanol, a zwlaszcza metanol i etanol; cykliczne etery jak tetrahydrofu- ran i dioksan.Do katalitycznego uwodorniania katalizator stosuje sie z reguly w ilosci 5-30% wagowych, w stosunku do zasady Schiffa. Katalizator stosuje sie ewentualnie w mieszaninie z odpowiednim dla reakcji nosnikiem, np. dwutlenkiem krzemu, przy czym korzystnie katalizator stosuje sie w ilosci stanowiacej 10-40% wagowych mieszaniny katalizatora z nosnikiem.Jako katalizatory stosuje sie korzystnie chromin miedzi, np. tlenek miedziowo-chromowy, jak stosowane przez H. Adkins'a chromiany miedzi, np. Houben-Weyl, Methoden der organischen Chemie, tom 4/2, strony 180-183 oraz J. Applied Chem. 5, 289-295 (1955). Zawieraja one na przyklad spinel miedziowo-chromowy (CuCr204) albo mieszaniny w stosunku 5CuO:4Cr203 wzglednie pochodza od takich zwiazków i moga zawierac jeszcze inne tlenki, glówne tlenki metali ziem alkalicznych jak magnezu, wapnia lub baru.Ponizsze opisy objasniaja sposób wytwarzania 2-metylonaftyloamin o wzorze ogólnym 2. a) Bezposrednie alkilowanie l-amino-2-metylonaftalenu wedlug schematu 1 144,2 g (0,92 mola) l-amino-2-metylonaftalenu, 90,2 g (1,08 mola) wodoroweglanu sodowego i 460 g (2,76 mola) estru metylowego kwasu 2-bromopropionowego miesza sie przez 18 godzin w temperaturze 120-125°C. Po ochlodzeniu odsacza sie osad pod zmniejszonym cisnieniem, a przesacz zateza tez pod zmniejszonym cisnieniem. Pozostalosc destyluje sie pod zmniejszonym cisnieniem i tak otrzymuje 188 g, co odpowiada 83,7% wydajnosci teoretycznej, estru metylowego N-(2-metylo-l-naftylo)-alaniny w postaci bezbarwnego oleju o temperaturze wrzenia 138-140°C/20 Pa. b) Wytwarzanie zasady Schiffa l-amino-2-metylonaftalenu wedlugschematu2 314 g (2 mole) l-amino-2-metylonaftalenu, 232 g (2 mole) estru etylowego kwasu pirogrono- wego i 0,4 g kwasu p-toluenosulfonowego w 1000 ml cykloheksanu ogrzewa sie przez 4 godziny do wrzenia pod chlodnica zwrotna, az oddestyluje azeotropowo 36 g wody, która odziela sie z123 432 5 destylatu. Nastepnie cykloheksan oddestylowuje sie pod zmniejszonym cisnieniem, a pozostalosc poddaje bezposrednio dalszej reakcji. Wydajnosc zasady Schiffa: 494,7g, co odpowiada 97% wydajnosci teoretycznej; wedlugschematu3 314 g l-amino-2-metylonaftalenu, 236gacetalu dimetylowego metyloglioksalu i 0,4g kwasu p-toluenosulfonowego poddaje sie reakcji analogicznie do sposobu wedlug schematu 2. Wydajnosc zasady Schiffa: 493,4g, co odpowiada 96% wydajnosci teoretycznej. c) Uwodornianie zasady Schiffa Kata lityczne uwodornianie wedlug schematu 4 W autoklawie do uwodorniania o pojemnosci 11 umieszcza sie 200 g zasady Schiffa, wytwo¬ rzonej z l-amino-2-metylonaftalenu i estru etylowego kwasu pirogronowego, rozpuszczonej w 500 czesciach tetrahydrofuranu i 15 czesci katalizatora Adkins'a (chromian miedzi w postaci sproszko¬ wanej). Nastepnie ogrzewa sie autoklaw do temperatury 150°C i wprowadza wodór az do uzyska¬ nia cisnienia 20 MPa. Po okolo 9 godzinach zostaje zakonczone pochlanianie wodoru i uzyskuje sie stale cisnienie. Wówczas ochladza sie mieszanine reakcyjna, odsacza katalizator pod zmniejszo¬ nym cisnieniem i przesacz zateza równiez pod zmniejszonym cisnieniem. Otrzymuje sie 142 g, co odpowiada 71% wydajnosci teoretycznej, estru etylowego N-(2-metylo-l-naftylo)-alaniny w postaci bezbarwnego oleju o temperaturze wrzenia 144-145°C/15Pa.Redukcjawodorkiem sodów o-b o r o w y m 490 g zasady Schiffa, otrzymanej z 1-amino-2-metylo-naftalenu i acetalu dimetylowego metyloglioksalu, rozpuszcza sie w 1500 ml metanolu i do roztworu tego dodaje porcjami w temperaturze 0°C 60 g wodorku sodowo-borowego. Miesza sie przez noc, po czym oddestylowuje metanol, pozostalosc rozpuszcza w 1000 ml chlorku metylenu i miesza przez 30 minut z 500 ml 10% lugu potasowego, po czym oddziela faze organiczna i przemywaja 3 razy woda, stosujac kazdora¬ zowo 200 ml, a nastepnie suszy siarczanem sodowym, oddestylowuje chlorek metylenu i pozosta¬ losc poddaje destylacji pod zmniejszonym cisnieniem. Otrzymuje sie 367 g, co odpowiada 74% wydajnosci teoretycznej, acetalu dimetylowego 2-(N-2'-metylo-1 '-naftylo)-aminopropanalu o terti- peraturze wrzenia 140-145°C/30Pa.Jako korzystne zwiazki o wzorze ogólnym 1 wymienia sie nastepujace: ester metylowy N-/( 1 -pirazolilo)-acetylo)-N-(2'-metylo-1 '-naftylo^alaniny, ester etylowy N-/(]-pirazolilo)-acetylo/-N-(2l-metylo-r-naftylo)-alaniny, ester metylowy N-/(l ,2,4-triazol-l-ilo)-acetylo/-N-(2,-metylo-r-naftylo)-alaniny, ester etylowy N-/(1,2,4-triazol- l-ilo)-acetylo/-N-(2'-metylo-( 1 '-naftylo)-alaniny, ester metylowy N-cyklopropylokarbonylo-N-(2-metylo-l-naftylo)-alaniny, ester etylowy N-cyklopropylokarbonylo-N-(2-metylo-1 -naftylo)-alaniny, ester metylowy N-cyklopentylokarbonylo-N-(2-metylo- l-naftylo)-alaniny, ester metylowy N-cykloheksylokarbonylo-N-(2-metylo- l-naftylo)-alaniny, ester metylowy N-metoksykarbonylo-N-(2-metylo-1 -naftylo)-alaniny, ester metylowy N-etoksykarbonylo-N-(2-metylo-l-naftylo)-alaniny, ester etylowy N-etoksykarbonylo-N-(2-metylo-l-naftylo)-alaniny, ester metylowy N-propoksykarbonylo-N-(2-metylo-1 -naftylo)-alaniny, ester metylowy N-alliloksykarbonylo-N-(2-metylo- l-naftylo)-alaniny, ester metylowy N-butoksykarbonylo-N-(2-metylo-l-naftylo)-alaniny, ester metylowy N-metoksalilo-N-(2-metylo-l-naftylo)-alaniny, ester metylowy N-etoksyalilo-N-(2-metylo-l-naftylo)-alaniny, ester etylowy N-etoksalilo-N-(2-metylo-l-naftylo)-alaniny, ester metylowy N-acetoacetylo-N-(2-metylo-l-naftylo)-alaniny, ester metylowy N-(4-oksopentanoilo)-N-(2'-metylo-1 '-naftylo)-alaniny, ester metylowy N-(3-hydroksybutyrylo)-N-(2'-metylo-r-naftylo)-alaniny, ester metylowy N-benzoilo-N-(2-metylo-l -naftylo)-alaniny, ester metylowy N-(2-chlorobenzoilo)-N-(2'-metylo-1 '-naftylo)-alaniny, ester metylowy N-(2-bromobenzoilo)-N-(2,-metylo-1'-naftylo)-alaniny, ester metylowy N-(2-jodobenzoilo)-N-(2'-metylo-1 '-naftylo)-alaniny, ester metylowy N-(2-metylobenzoilo)-N-(2'-metylo-1 '-naftylo)-alaniny,6 123432 ester metylowy N-^-trifluorometylobenzoilo^N-y-metylo-1 '-naftylo)-alaniny, ester metylowy N-(2-metoksybenzoilo)-N-(21-metylo-1 '-naftylo^alaniny, ester metylowy N-^-tiofenokarbonylo^N-^Z-metylo-1 '-naftylo^alaniny, ester metylowy N-(2-furanokarbonylo)-N-(2,-metylo-r-naftylo)-alaniny, ester etylowy N-(2-furanokarbonylo)'-N-(2,metylo-r-nattylo)-alaniny, ester metylowy N-(2-metylofurano-3-karbonylohN-(2'-metylo-1 '-naftylo)-alaniny, ester metylowy N-(2,5-dimetyloturano-3-karbonylo)-N-(2,-metylo-l,-naftylo)-alaniny, ester metylowy N-(2,4,5-trimetylofurano-3-karbonylo)-N-(2,-metylo-r-naftylo)-alaniny, ester metylowy N-(3-izoksazolilokarbonylo)-N-(2'-metylo-1 '-naftylo)-alaniny, ester etylowy N-(3-izoksazolilokarbonylo)-N-(2'-metylo-1 '-naftylo)-alaniny, ester metylowy N-(3-metyloizoksazolilo-5-karbonylo)-N-(2'-metylo- ] '-naftylo)-alaniny, ester metylowy N-nikotynoilo-N-(2-metylo-]-naftylo)-alaniny, ester metylowy N-(2-chloronikotynoilo)-N-(2,-metylo-l'-naftylo)-alaniny, ester metylowy N-akryloilo-N-(2-metylo-l-naftylo)-alaniny, ester metylowy N-(2-metyloakry!oilo)-N-(2,-metylo-l,-naftylo)-alaniny, ester metylowy N-fenoksykarbonylo-N-(2-metylo-l-naftylo)-alaniny, ester metylowy N-(4-chlorofenoksykarbonylo)-N-(2'-metylo- ] '-naftylo)-alaniny, acetal dimetylowy 2-/N-(2-metylo-l-naftylo)-N-acetylo/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo-l-naftylo)-N-propionylo/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo- l-naftylo)-N-butyrylo/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo-1 -naftylo)-N-chloroacetylo/-aminopropanalu, N-/l-(] ,,3'-dioksolan-2,-ylo)-etyloAN-(2,,-metylo-r,-naftylo)-amid kwasu chlorooctowego, N-/l-(4,-metylo-r,3,-dioksolan-2,-ylo)-etylo/-N-(2,,-metylo-r,-naftylo)-amid kwasu chloroocto¬ wego, acetal dimetylowy 2-/N-(2-metylo-1 -naftylo)-N-bromoacetylo/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo- J-naftylo)-N-jodoacetylo/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo-1 -naftylo)-N-metoksyacetylo/-aminopropanalu, N-/l-(l,,3,-dioksolan-2,-ylo)-etylo/-N-(2"-metylo-l,,-naftylo)-amid kwasu metoksyoctowego, N-/l-(4'-metylo-r,3'-dioksolan-2,-ylo)-etylo/-N-(2,,-metylo-r,-naftylo)-amid kwasu metoksy¬ octowego, N-/l-(4,,5,-dimetylo-l,,3,-dioksolan-2,-ylo)-etylo/-N-(2"-metylo-r,-naftylo)-aniid kwasu meto¬ ksyoctowego, -naftylo)-N-etoksykarbonylo/-aminopropanalu, -naftylo)-N-metylotioacetylo/-aminopropanalu, -naftylo)-N-(2,-chloropropionylo)/-aminopropanalu, -naftylo)-N-( 1 Mmidazoliloacetylo)/-aminopropanalu, -naftylo)-N-( 1 '-pirazoliloacetylo)/-aminopropanalu, -naftyloJ-N^r^/j^-triazol-r-iloacetyloy-aminopropanalu, -naftylo)-N-cyklopropylokarbonylo/-aminopropanalu, -naftylo)-N-cykloheksylokarbonylo/-aminopropanalu, -naftylo)-N-metoksykarbonylo/-aminopropanalu, -naftylo)-N-etoksykarbonylo/-aminopropanalu, -naftylo)-N-butoksykarbonylo/-aminopropanalu, -naftylo)-N-alliloksykarbonylo/-aminopropanalu, -naftylo)-N-metoksalilo/-aminopropanalu, -naftylo)-N-etoksalilo/-aminopropanalu, -naftylo)-N-acetoacetylo/-aminopropanalu, N-(2,,-metylo-l"-naftylo/-amid kwasu acetylooctowego, -naftylo)-N-(3'-hydroksybutyrylo)/-aminopropanalu, -naftylo)-N-benzoilo/-aminopropanalu, ~naftylo)-N-(2'-chk)robenzoilo)/-aminopropanalu, -naftylo)-N-(2'-bromobenzoilo)/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo~ acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo~ acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- N-Zl-Cr^T-dioksolan-r-yloHtylo/ acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo- acetal dimetylowy 2-/N-(2-metylo-123432 7 acetal dimetylowy 2-/N-(2-metylo-l-naftylo)-N-(2,-trifluorometylobenzoilo)/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo~l-naftylo)-N-(2,-metoksybenzoilo)/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo-l-naftylo)-N-(2'-furanokarbonylo)/-aminopropanalu, N-/l-(l,,3,-dioksolan-2,-ylo)-etylo/-N-(2,,-metylo-l,,-naftylo)-amid kwasu 2-furanokarboksylo- wego, acetal dimetylowy 2-/N-(2-metylo-l-naftylo)-N-(2,-metylo-furano-3'-karbonylo)/-aminopropa- nalu, acetal dimetylowy 2-/N-(2-metylo-l-naftylo)-N-(2,,4,,5,-trimetylofurano-3,-karbonylo)/-amino- propanalu, acetal dimetylowy 2-/N-(2-metylo-1-naftylo)-N-(3Mzoksazolilokarbonylo)/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo-1 -naftylo^N-^-metyloizoksazolilo-S^karbonyloy-aminopro- panalu, acetal dimetylowy 2-/N-(2-metylo-1 -naftylo)-N-nikotynoilo)/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo-1 -naftylo)-N-(2/-chloronikotynoilo)/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo-1 -naftylo)-N-akryloilo/-aminopropanalu, acetal dimetylowy 2-/N-(2-metylo-1 -naftylo)-N-(4,-chlorofenoksykarbonylo)/-aminopropanalu, ester metylowy N-(2-furanokarbonylo)-N-(2'-metylo-4,-bromo-l '-naftylo)-alaniny, ester metylowy N-metoksyacetylo-N-(2-metylo-4-bromo- l-naftylo)-alaniny, 2-/N-(2-metylo-l-naftylo)-N-bromoacetylo/-aminopropanal, 2-/N-(2-metylo-J-naftylo)-N-metoksyacetylo/-aminopropanal.Ponizsze przyklady objasniaja wytwarzanie nowych zwiazków sposobem wedlug wynalazku, nie ograniczajac jego zakresu.Przyklad I. Wytwarzanie zwiazku o wzorze 4. Mieszanine zlozona z 30,7 g (0,12 mola) estru metylowego N-(2-metylo-l-naftylo)-alaniny, 9,5 g (0,12 mola) pirydyny, 5 g 4-dimetyloaminopiry- dyny i 50 ml bezwodnika octowego miesza sie w temperaturze 80°C przez 8 godzin, po czym chlodzi i zateza pod zmniejszonym cisnieniem. Pozostalosc zadaje sie 250 ml eteru dwuetylowego i 250ml wody. Oddziela sie faze organiczna, przemywaja 100 ml 1 N kwasu solnego, a potem 100 ml wody, a nastepnie odbarwia weglem i zateza. Pozostalosc miesza sie w temperaturze 0°C z 30 ml mieszaniny eteru naftowego i eteru dwuetylowego w stosunku 5:1, a potem pozostawia na 4 godziny w temperaturze 0°C do wykrystalizowania. Tak otrzymuje sie 23,6 g, co odpowiada 69% wydajnosci teoretycznej, estru metylowego N-acetylo-N-(2-metylo-l-naftylo)-alaniny w postaci bialych krysztalów o temperaturze topnienia 119-121°C.Przyklad II. Wytwarzanie zwiazku o wzorze 5. Do mieszanej energicznie zawiesiny 14g (0,17 mola) wodoroweglanu sodowego i 20 g siarczanu sodowego w 150 ml suchego toluenu dodaje sie 19,4g (0,09 mola) estru metylowego N-(2-metylo-l-naftylo)-alaniny i nastepnie w ciagu 1 godziny w temperaturze +15°C wkrapla sie roztwór 24,2 g (0,12 mola) bromku bromoacetylu w 50 ml toluenu. Calosc miesza sie przez 5 godzin w temperaturze 25°C, po czym odsacza osad pod zmniejszonym cisnieniem i przemywa go 50 ml toluenu. Przesacz przemywa sie 2 razy 1 N lugiem sodowym, stosujac kazdorazowo 100 ml, raz 50 ml 2N kwasu solnego i wreszcie 100 ml wody, suszy, odbarwia weglem i zateza pod zmniejszonym cisnieniem. Oleista pozostalosc suszy sie przez 3 godziny w temperaturze 50°C pod cisnieniem 10 Pa. Takotrzymuje sie 22,5 g co odpowiada 77,3% wydajnosci teoretycznej, estru metylowego N-bromoacetylo-N-(2-metylo-l-naftylo)-alaniny w postaci jasnozóltego oleju.Widmo IR (film): 3035, 2970, 2935, 1730, 1652, 1440, 1415, 1360, 1200, 1132, 1095, 812, 782, 744 cm"1 Przyklad III. Wytwarzanie zwiazku o wzorze 6. 13g (0,036mola) estru metylowego N- bromoacetylo-N-(2-metylo-l-naftylo)-alaniny (przyklad II) rozpuszcza sie w 60 ml suchego dime¬ tyloformamidu i zadaje 6,8 g (0,1 mola) imidazolu. Calosc miesza sie przez 10 godzin w temperaturze 60°C i zateza pod zmniejszonym cisnieniem. Pozostalosc wytrzasa sie ze 150ml chlorku metylenu i 50 ml wody, odziela warstwe organiczna i przemywaja 2 razy woda, stosujac kazdorazowo 50 ml. Roztwór organiczny suszy sie, odbarwia weglem i zateza. Po oczyszczeniu surowego produktu przez saczenie jego roztworu w octanie etylu przez zel krzemionkowy i zatezenie otrzymuje sie jako pozostalosc 9,6 g zywicy.8 123432 Analiza: obliczono: C 68,4 H 6,0 N 12,0% znaleziono: C 68,0 H 6,4 N 11,9% Przyklad IV. Wytwarzanie zwiazku o wzorze 7. Do 24,3g (OJ mola) estru metylowego N-(2-metylo-l-naftylo)-alaniny i 0,5 ml trietyloaminy w 50 ml suchego toluenu wkrapla sie przy mieszaniu w temperaturze 90°C 9g (0,1 mola) diketenu. Calosc miesza sie przez 3 godziny w temperaturze 95°C, po czym ochladza, przemywa raz 50 ml 2 N kwasu solnego i raz woda, suszy i zateza. Surowy produkt oczyszcza sie przez przesaczenie jego roztworu w octanie etylu przez zel krzemionkowy, po czym odparowuje octan etylu i tak otrzymuje sie 29,7 g, co stanowi 90% wydajnosci teoretycznej, pozostalosci w postaci analitycznie czystego oleju.Widmo IR (film): 3042, 2980, 2940, 1740, 1720, 1650, 1650, 1455, 1370, 1310, 1195, 920, 815, 786, 746cm_1.Przyklad V. Wytwarzanie zwiazku o wzorze 8, 22,2 g (0,066 mola) estru metylowego N-(2- furanokarbonylo)-N-(2,-metylo-r-naftylo)-alaniny (przyklad XXI) i 6g (0,07 mola) bezwodnego octanu sodowego w 150 ml kwasu octowego zadaje sie 11 g (0,067 mola) bromu i miesza przez 24 godziny w temperaturze 35°C. Nastepnie calosc miesza sie z 700ml wody z lodem i produkt ekstrahuje 3 razy eterem, stosujac kazdorazowo 100 ml. Polaczone ekstrakty eterowe przemywa sie raz 100 ml 1 N lugu sodowego i raz woda, suszy i zateza. Tak otrzymuje sie 17 g, czyli 62% wydajnosci teoretycznej, estru metylowego N-(2-furanokarbonylo)-N-(2'-metylo-4'-bromo-r- naftylo)-alaniny w postaci bezbarwnej zywicy.Widmo IR (film): 3035, 2930, 1730, 1640, 1450, 1360, 1235, 1190, 1126, 1092,908, 810 cm"1.Przyklad VI. Wytwarzanie zwiazku o wzorze 9. 14,2g (0,04mola) acetalu dimetylowego 2-/N-(2-metylo-l-naftylo)-N-(2'-furanokarbonylo)/-aminopropanalu (przyklad XXIII) 3ml gli¬ kolu etylenowego i 0,2 g kwasu p-toluenosulfonowego w 80ml toluenu miesza sie w temperaturze 80°C przez 8 godzin. Powstajacy przy tym metanol usuwa sie stale z mieszaniny reakcyjnej slabym strumieniem azotu. Po ochlodzeniu i trzykrotnym przemyciu woda, stosujac kazdorazowo 60 ml, organiczny roztwór odbarwia sie weglem i zateza. Pozostalosc krystalizuje po dodaniu 10 ml zimnego eteru. Tak otrzymuje sie 9g, co odpowiada 64% wydajnosci teoretycznej, N-/l-(l',3'- dioksolan-2,-ylo)-2-metylo-etylo/-N-(2,,-metylo-r,-naftylo)-amidu kwasu 2-furanokarboksylo- wego w postaci bialych krysztalów o temperaturze topnienia 129-131°C.Przyklad VII. Wytwarzanie zwiazku o wzorze 10. Roztwór 7,6 g (0,02 mola) acetalu dime¬ tylowego 2-/N-(2-metylo-l-naftylo)-N-bromoacetylo/-aminopropanalu (przyklad XII) w 50 ml chlorku metylenu miesza sie energicznie przez 1 godzine w temperaturze pokojowej ze 100 ml 2N kwasu solnego. Oddziela sie faze organiczna, przemywa ja 100 wody, suszy i zateza. Takotrzymuje sie 5,3g, co odpowiada 80% wydajnosci, teoretycznej 2-/N-/2-metylo-l-naftylo/-N-bromoacety- loAaminopropanalu w postaci jasnozóltego oleju.Widmo IR (film): 3038, 2970, 2820, 2710, 1720, 1645, 1490, 1365, 1203, 810, 778, 742, 640 cm"1.Analogicznie wytwarza sie zwiazki o wzorze ogólnym 1, które szczególowo przedstawione sa w tablicy I.Nowe substancje czynne wykazuja silne dzialanie grzybobójcze przeciw grzybom powoduja¬ cym choroby roslin, szczególnie z klasy Phycomyceten. Z tego wzgledu sa one odpowiednie przykladowo do zwalczania grzybów takich jak Phytophthora infestens na pomidorach i ziemnia¬ kach, Phytophthora parasitica na poziomkach, Phytophthora cactorum na jablkach, Pseudopero- nospora cubenis na ogórkach, Pseudoperonospora humuli na chmielu, Peronosporadestructor na cebuli, Peronospora sparsa na rózach, Peronospora tabacica na tytoniu, Plasmopara viticola na winoroslach, Plasmopara halstedii na slonecznikach, Sclerospora na kukurydzy, Bremia lactocae na salacie, Mucor mucedo na owocach, Rhizopus nigricans na rzepie, Erysiphe graminis na zbozu, Uncinula necator na winoroslach, Podophaera leucotricha na jablkach, Sphaerotheca fuliginea na rózach, Erysiphe cichoriacearum na ogórkach.Srodek grzybobójczy wedlug wynalazku zawiera 0,1-95% wagowych, zwlaszcza 0,5-90% wagowych substancji czynnej. Zaleznie od pozadanego efektu stosuje sie 0,1-5 kg substancji czynnej na hektar. Czesc substancji czynnych srodka wedlug wynalazku wykazuje wlasciwosci123432 9 lecznicze, to znaczy w celu uzyskania pewniejszego efektu zwalczania, substancje czynne stosuje sie jeszcze po nastapieniu zakazenia roslin przez zarazki. Dobre dzialanie grzybobójcze wykazuja substancje czynne o uziarnieniu mniejszym nie 5 /i.Ponadto wiele z nowych substancji czynnych dziala ukladowo tak, ze przez traktowanie korzeni mozna chronic takze nadziemne czesci roslin.Substancje czynne srodka wedlug wynalazku mozna mieszac i nanosic razem z innymi substancjami czynnymi, np. srodkami chwastobójczymi, owadobójczymi, regulatorami wzrostu i srodkami grzybobójczymi albo tez z nawozami. Przy mieszaniu ze srodkami grzybobójczymi w wielu przypadkach uzyskuje sie takze rozszerzenie grzybobójczego zakresu dzialania. W przy¬ padku pewnej liczby tych mieszanek grzybobójczych wystepuja takze efekty synergetyczne, to znaczy skutecznosc grzybobójcza produktu kombinowanego jest wieksza niz suma skutecznosci poszczególnych skladników. Szczególnie korzystne rozszerzenie zakresu dzialania uzyskuje sie ze srodkami grzybobójczymi takimi jak: etyleno-bis-ditiokarbaminian manganawy, etyleno-bis-ditiokarbaminian manganawo-cynkowy, N,N-etyleno-bis-ditiokarbaminian cynkowo-amonowy, N-trichlorometylotiotetrahydroftalimid, N-trichlorometyloftalimid, 5-etoksy-3-trichlorometylo-1,2,3-tiadiazol, 2-metoksykarbonyloaminobenzimidazol, 2-rodanometylotiobenzotiazol, J,4-dichloro-2,5-dimetoksybenzen, anilid kwasu 2,3-dichloro-6-metylo-l,4-oksatiino-5-karboksylowego, anilid kwasu 2-metylo-5,6-dihydro-4-H-pirano-3-karboksylowego, anilid kwasu 2,4,5-trimetylofurano-3-karboksylowego, anilid kwasu 2-metylofurano-3-karboksylowego, cykloheksyloamid kwasu 2,5-dimetylofurano-3-karboksylowego, N-cykloheksylo-N-metoksyamid kwasu 2,5-dimetylofurano-3-karboksylowego, 5-metylo-5-winylo-3-(3,5-dichlorofenylo)-2,4-diokso-l,3-oksazolidyna oraz 3-(3,5-dichlorofenylo)-5-metylo-5-metoksymetylo-l,3-oksazolidyno-2,4-dion.Ponizsze zestawienie srodków grzybobójczych, z którymi mozna mieszac substancje czynne srodka wedlug wynalazku, powinno objasnic, ale nie ograniczyc, mozliwosci kombinacji.Srodkami grzybobójczymi, które mozna mieszac z substancjami czynnymi srodka wedlug wynalazku, sa przykladowo: ditiokarbaminiany oraz ich pochodne, jak: dimetyloditiokarbaminian zelazowy, dimetyloditiokarbaminian cynkowy, etyleno-bis-ditiokarbaminian cynkowy, dwusiarczek tetrametylotiuramu, N,N-propyleno-bis-ditiokarbaminian cynkowy, N,N'-propyleno-bis-ditiokarbaminian cynkowo-amonowy i dwusiarczek NjN^polipropyleno-bis-tiokarbamylu, pochodne nitrowe, jak dinitro-( 1 -metyloheptylo)-fenylokrotonian, 2-sec-butylo-4,6-dinitrofenylo-3,3-dimetyloakrylan, 2-sec-butylo-4,6-dinitrofenyloizopropylokarboksylan, zwiazki o budowie heterocyklicznej, jak 2-heptadecylo-2-imidazolinooctan, 2,4-dichloro-6-(o-chloroanilino)-s-triazyna, O,0-dietyloftalimidotiofosfonian, 5-amino-J-(bis-dimetyloamino-fosfinylo)-3-fenylo-],2,4-triazol, 2,3-dicyjano-l,4-ditiaantrachinon, 2-tio-l ,3-ditio-(4,5-b)-chinoksalina, ester metylowy kwasu l-(butylokarbamylo)-2-benzimidazolokarbaminowego, 4-(2-chlorofenylohydrazono)-3-metylo-5-izoksazolon,10 123 432 1-tlenek pirydyno-2-tiolu, 8-hydroksychinolina wzglednie jej sole z miedzia, 4,4-ditlenek 2,3-dihydro-5-karboksyanilido-6-metylo-1,4-oksatiiny, 2,3-dihydro-5-karboksyanilido-6-metylo-l,4~oksatiina, 2-(2-furylo)-benzimidazol, piperazyn-1,4-diylo-bis-/] -(2,2,2-trichloroetylo)-formamid/, 2-(4-tiazolilo)-benzimidazol, 5-butylo-2-dimetyloamino-4-hydroksy-6-metylopirymidyna, bis-(p-chlorofenylo)-3-pirydynometanol, l,2-bis-(3-etoksykarbonylo-2-tioureido)-benzen, l,2-bis-(3-metoksykarbonylo-2-tioureido)-benzen oraz rózne srodki grzybobójcze, jak: octan dodecyloguanidyny, 3-/3-(3,5-dimetylo-2-oksycykloheksylo)-2-hydroksyetylo/-glutarimid, heksachlorobenzen, N-dichlorofluorometylotio-N,,N1-dimetylo-N-fenylodiamid kwasu siarkowego, anilid kwasu 2,5-dimetylofurano-3-karboksylowego, anilid kwasu 2-metylobenzoesowego, anilid kwasu 2-jodobenzoesowego, l-(3,4,-dichloroanilino)-l-formyloamino-2,2,2-trichloroetan, 2,6-dimetylo-N-tridecylomorfolina wzglednie jej sole, 2,6-dimetylo-N-cyklododecylomorfolina wzglednie jej sole, l-(4-chlorenoksy)-3,3-dimetylo-1 -(1H-1,2,4-triazol-1 -ilo)-2-butanon, l-(4-chlorofenoksy)-3,3-dimetylo-1 -(1H-1,2,4-triazol-1 -ilo)-2-butanol oraz a-(2-chlorofenylo)-a-(4-chlorofenylo)-5-pirymidynometanol.Substancje czynne srodka wedlug wynalazku stosuje sie przykladowo w postaci odpowiednich do bezposredniego rozpylania roztworów, proszków, zawiesin, takze wysokoprocentowych wodnych, olejowych albo innych zawiesin lub dyspersji, emulsji, dyspersji olejowych, past, srodków do opylania, srodków do posypywania lub granulatów, przez opryskiwanie, rozpylanie mglawicowe, opylanie, posypywanie, zaprawianie lub polewanie. Zastosowana postac zalezy calkowicie od celu stosowania i w kazdym przypadku powinna zapewnic mozliwie jak najlepsze rozprowadzenie substancji czynnej. Uziarnienie mozne wplywac na dzialanie substancji czynnej, a mianowicie stwierdzono, ze ze wzrastajaca mialkoscia substancji czynnej polepsza sie dzialanie grzybobójcze jej.Do wytworzenia odpowiednich do bezposredniego rozpylania roztworów, emulsji, past i dyspersji olejowych stosuje sie frakcje oleju mineralnego o temperaturze wrzenia od sredniej do wysokiej, jak nafte albo olej do silników Diesla, dalej oleje ze smoly weglowej, itd.,jak równiez oleje pochodzenia roslinnego i zwierzecego, alifatyczne, cykliczne i aromatyczne weglowodory, na przyklad benzen, toluen, ksylen, parafine, tetrahydronaftalen, alkilowane naftaleny albo ich pochodne, np. metanol, etanol, propanol, butanol, chloroform, czterochlorek wegla, cykloheksanol, cykloheksanon, chlorobenzen, izoforon itd., silnie polarne rozpuszczalniki,jak np. dimetyloformamid, dimetylosulfotlenek, N-metylopirolidon, wode itd.Wodne postacie zastosowan przygotowuje sie przez dodanie wody do koncentratów emulsyjnych, past, proszków zawiesinowych albo dyspersji olejowych. W celu wytworzenia emulsji, past albo dyspersji olejowych substancje jako takie lub rozpuszczone w oleju albo rozpuszczalniku homogenizuje sie w wodzie przy uzyciu srodków zwilzajacych, zwiekszajacych przyczepnosc, dyspergujacych albo emulgujacych. Postepuje sie ewentualnie takze w ten sposób, ze wytwarza sie odpowiednie do rozcienczania woda koncentraty skladajace sie z substancji czynnej, srodka zwilzajacego, zwiekszajacego przyczepnosc, dyspergujacego albo emulgujacego i ewentualnie rozpuszczalnika lub oleju.Jako substancje powierzchniowo czynne stosuje sie sole metali alkalicznych, metali ziem alkalicznych i sole amonowe kwasu ligninosulfonowego, kwasów naftalenosulfonowych i kwasu fenolosulfonowego, alkiloarylosulfoniany, alkanosulfoniany, siarczany alkilowe, sole metali123432 11 alkalicznych i metali ziem alkalicznych kwasu dibutylonaftalenosulfonowego, siarczanowany oksyetylenowany alkohol laurylowy, siarczany alkoholi tluszczowych, sole metali alkalicznych i metali ziem alkalicznych kwasów tluszczowych, sole siarczanowanych heksadekanoli, heptadekanoli i oktadekanoli, sole siaczanowanego eteru glikolu i alkoholu tluszczowego, produkty kondensacji sulfonowanego naftalenu i pochodnych naftalenu z formaldehydem, produkty kondensacji naftalenu wzglednie kwasów naftalenosulfonowych z fenolem i formaldehydem, eter oktylofenolowy polioksyetylenu, etoksylowany izooktylofenol, oktylofenol i nonylofenol, etery alkilofenolowe poliglikolu, eter tributylofenylowy poliglikolu, alkiloarylopoli- eteroalkohole, alkohol izotridecylowy, produkty kondensacji alkoholi tluszczowych z tlenkiem etylenu, etoksylowany olej rycynowy, etery alkilowe polioksyetylenu, etoksylowany polioksypro- pylen, acetaloeter laurylowy poliglikolu, estry sorbitu, lignine, lugi posiarczynowe i metyloceluloze.Proszki, srodki do posypywania i opylania wytwarza sie przez zmieszanie lub wspólne zmielenie substancji czynnych ze stalym nosnikiem.Granulaty, np. granulaty w otoczkach, nasycane i jednorodne, wytwarza sie przez polaczenie substancji czynnych ze stalymi nosnikami takimi jak np. ziemie mineralne, jak silikazel, kwasy krzemowe, zele krzemionkowe, krzemiany, talk, kaolin, glinka Attaclay, wapien, kreda, glinka bolus, less, glina, dolomit, diatomit, siarczan wapniowy i magnezowy, tlenek magnezowy, zmielone tworzywa sztuczne, nawozy, jak np. siarczan amonowy, fosforan amonowy, azotan amonowy, moczniki i produkty roslinne, jak maki zbozowe, maczka z kory drzewnej, drewna i lupin orzechów, sproszkowana celuloza oraz inne stale nosniki.W przedstawionych ponizej doswiadczeniach jako znane, porównawcze substancje czynne zastosowano nastepujace zwiazki: N-trichlorometylotioftalimid — zwiazek A N-trichlorometylotiotetrahydroftalimid — zwiazek B etyleno-l,2-bis-ditiokarbaminian cynkowy — zwiazek C.Doswiadczenie 1. Dzialanie przeciwko chorobom wschodowym na grochu. 100 g próbki nasion grochu odmiany „Senator44 mieszano dokladnie przez okolo 5 minut w butelkach szklanych z 300 mg, co odpowiada 0,3% wagowych, preparatów do zaprawiania, zawierajacych w suchej masie 40% substancji czynnej. Nastepnie po 100 nasion z kazdej próbki zasiano na glebokosc 3 cm w odstepach 3-5 cm w skrzynkach wypelnionych ziemia kompostowa, która wykazywala silne naturalne zakazenie grzybami Pythium spec, Aphanomyces spec. i Fusarium oxysporum.Skrzynki ustawiono w cieplarni w temperaturze 17-20°C. Po uplywie 21 dni ustalono liczbe zdrowych roslin grochu.Uzyskane wyniki doswiadczenia przedstawione sa w tablicy II.Doswiadczenie?,. Dzialanie przeciwko Erysiphe graminis na pszenicy. Liscie rosnacych w doniczkach siewek pszenicy odmiany „Jubilar" opryskano wodnymi zawiesinami zlozonymi z 80% (procenty wagowe) substancji czynnej i 20% emulgatora. Po przyschnieciu powloki powstalej z opryskiwania opylono rosliny zarodnikami maczniaka pszenicy (Erysiphe graminis var. tritici).Nastepnie rosliny doswiadczalne ustawiono w cieplarni w temperaturze 20-22°C i wilgotnosci wzglednej powietrza 75-80%. Po 10 dniach oceniono rozmiar rozwoju grzyba maczniaka.Otrzymane wyniki doswiadczenia przedstawione sa w tablicy III.Doswiadczenie 3. Dzialanie przeciwko Phytophthora infestans na pomidorach. Liscie rosnacych w doniczkach roslin pomidorów odmiany „Grosse Fleischtomate" opryskano wodnymi zawiesinami, zawierajacymi 0,025% (procenty wagowe) substancji czynnej. Po przyschnieciu pow¬ loki powstalej z opryskiwania zakazono liscie zawiesina zarodnika plywkowego grzyba Phytopht¬ hora infestans. Nastepnie ustawiono rosliny w komorze o nasyconej parze wodnej i temperaturze 16-18°C. Po 5 dniach na nie traktowanych ale zakazonych roslinach kontrolnych choroba rozwi¬ nela sie tak silnie, ze mozna bylo ocenic grzybobójcze dzialanie badanych substancji.Uzyskane wyniki przedstawione sa w tablicy IV.Doswiadczenie 4. Dzialanie przeciw Plasmopara viticola na winoroslach. Liscie donicz¬ kowych winorosli odmiany „Muller-Thurgau" opryskano wodnymi zawiesinami, zawierajacymi 0,025% (procenty wagowe) substancji czynnej. Aby ocenic okres dzialania substancji czynnych,po12 123432 przyschnieciu powloki powstalej z opryskiwania rosliny ustawiono w cieplarni na 10 dni. Dopiero potem zakazono liscie zawiesina zarodnika plywkowego grzyba Plasmopara viticola, a nastepnie ustawiono rosliny najpierw na 16 godzin w komorze o nasyconej parze wodnej i temperaturze 24°C, a potem na 8 dni w cieplarni w temperaturze 20-30°C. Po tym czasie, w celu przyspieszenia wybicia sie trzonków zarodnionosnych, ustawiono rosliny znowu w komorze o nasyconej parze wodnej na 16 godzin. Nastepnie dokonano oceny rozwoju grzyba na dolnej stronie lisci.Uzyskane wyniki przedstawione sa w tablicy V.Nizej przedstawione sa przyklady wykonania preparatów.I. 90 czesci wagowych zwiazku z przykladu I miesza sie z 10 czesciami wagowymi N-metylo-a- pirolidonu i tak otrzymuje roztwór odpowiedni do stosowania w postaci bardzo drobnych kropel.II. 10 czesci wagowych zwiazku z przykladu II rozpuszcza sie w mieszaninie zlozonej z 90 czesci wagowych ksylenu, 6 czesci wagowych produktu przylaczenia 8-10 moli tlenku etylenu do 1 mola N-monoetanoloamidu kwasu olejowego, 2 czesci wagowych soli wapniowej kwasu dodecylo- benzenosulfonowego i 2 czesci wagowych produktu przylaczenia 40 moli tlenku etylenu do 1 mola oleju rycynowego.III. 20 czesci wagowych zwiazku z przykladu III rozpuszcza sie w mieszaninie zlozonej z 40 czesci wagowych cykloheksanonu, 30 czesci wagowych izobutanolu, 20 czesci wagowych produktu przylaczenia 40 moli tlenku etylenu do 1 mola oleju rycynowego. Przez wylanie i dokladne rozprowadzenie roztworu w 100000 czesci wagowych wody otrzymuje sie dyspersje wodna, zawierajaca 0,02% wagowe substancji czynnej.IV. 20 czesci wagowych zwiazku z przykladu I rozpuszcza sie w mieszaninie zlozonej z 25 czesci wagowych cykloheksanonu, 65 czesci wagowych frakcji oleju mineralnego o temperaturze wrzenia 210-280°C i 10 czesci wagowych produktu przylaczenia 40 moli tlenku etylenu do 1 mola oleju rycynowego. Przez wylanie i dokladne rozprowadzenie roztworu w 100 000 czesci wagowych wody otrzymuje sie wodna dyspersje, zawierajaca 0,02% wagowe substancji czynnej.V. 80 czesci wagowych zwiazku z przykladu II miesza sie dokladnie i miele w mlynku mlotkowym z 3 czesciami wagowymi soli sodowej kwasu diizobutylonaftaleno-a-sulfonowego, 10 czesciami wagowymi soli sodowej kwasu ligninosulfonowego z lugu posiarczynowego i 7 czesciami wagowymi sproszkowanego zelu krzemionkowego. Przez rozprowadzenie tej mieszaniny w wodzie otrzymuje sie ciecz do opryskiwania.VI. 3 czesci wagowe zwiazku z przykladu III miesza sie dokladnie z 97 czesciami wagowymi subtelnie rozdrobnionego kaolinu. Takotrzymuje sie srodek do opylania, zawierajacy 3% wagowe substancji czynnej.VII. 30 czesci wagowych zwiazku z przykladu I miesza sie doklanie z mieszanina zlozona z 92 czesci wagowych sproszkowanego zelu krzemionkowego i 8 czesci wagowych oleju parafinowego, którym opryskano powierzchnie tego zelu. W ten sposób otrzymuje sie preparat substancji czynnej o dobrej przyczepnosci.VIII. 40 czesci wagowych zwiazku z przykladu II miesza sie dokladnie z 10 czesciami soli sodowej kondensatu kwas fenolo-sulfonowy-mocznik-formaldehyd, 2 czesciami zelu krzemionko¬ wego i 48 czesciami wody. Tak otrzymuje sie trwala dyspersje wodna. Przez rozcienczenie jej 100000 czesci wagowych wody otrzymuje sie dyspersje wodna, zawierajaca 0,04% wagowe sub¬ stancji czynnej.IX. 20 czesci zwiazku z przykladu III miesza sie dokladnie z 2 czesciami soli wapniowej kwasu dodecylobenzenosulfonowego, 8 czesciami eteru alkoholu tluszczowego i poliglikolu, 2 czesciami soli sodowej kondensatu kwas fenolosulfonowy-mocznik-formaldehyd i 68 czesciami parafinowanego oleju mineralnego. Tak otrzymuje sie trwala dyspersje olejowa. PLThe patent description was published: May 15, 1984 Inventor entitled to the patent: BASF Aktiengesellschaft, Ludwigshafen (Federal Republic of Germany) Fungicide The subject of the invention is a fungicide containing new N-substituted 2-methylnaphthylamides as active substances. It is already known that ethylene-1,2 Zinc bis-dithiocarbamate, N-trichloromethylthiophthalimide and N-trichloromethylthiotetrahydrophthalimide are used as fungicides in agriculture and horticulture. The listed compounds are good agents for combating fungal diseases, e.g. R. Hungary, "Chemie der Pflanzenschutz- und Schadlingsbekampfungsmitter, vol. 2, pages 65-66 and 109 and vol. 4, pages 139 and 191, Berlin / Heidelberg / New York, (1970) and (1977). However, these fungicides are not suitable for post-infection use and their low concentration treatment does not meet the requirements of practice. The novel N-substituted 2-methylnaphthylamides of the general formula I have been found to exhibit potent fungicidal activity. of the formula —CO — R3, wherein R3 is a hydrogen atom or an alkoxy group of 1-4 carbon atoms, and further R1 is a group of the formula —CH / OR4 / —OR5, where R4 and R5 independently of each other represent an optionally substituted alkyl group of 1-4 carbon atoms or R4 and R5 together represent an alkylene group which together with the group to which it is substituted forms optionally substituted with an alkyl group of 1-4 carbon atoms or by an aryl group of a 5- or 6-membered heterocyclic ring containing 2 oxygen atoms and R2 is an alkyl group of 1-4 carbon atoms which is optionally substituted with a fluorine, chlorine, bromine or iodine atom, or an alkoxy group with 1-4 carbon atoms, an alkyl group thio with 1-4 carbon atoms, 1-imidazolyl, 1-pyrazolyl, 1,2,4-triazol-1-yl or keto, further R2 is alkenyl with 2-5 carbon atoms, alkynyl with 2-5 carbon, cycloalkyl 3-7 carbon, cycloalkenyl 4-7 carbon, alkoxy 1-5 carbon, optionally substituted phenyl or optionally substituted heteroaryl, and X is hydrogen, methyl, chlorine or In general formula I, R2 is preferably an unbranched or branched alkoxy group with 1-5 carbon atoms, for example a group such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy or isopentyloxy, or is optionally substituted by fluoro, chloro, bromo or iodo, by methoxy, ethoxy, butoxy, methylthio, ethylthio, 1-imidazolyl, 1-pyrazolyl or by group 1, 2,4-triazol-1-yl branched alb a non-ignited alkyl group having 1 to 4 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. R2 is moreover, for example, a vinyl, 1-propenyl, 2-propenyl, allyl, ethynyl group or, for example, an oyclic alkyl or alkenyl group with 3-7 carbon atoms in the ring, for example a cyclopropyl, cyclopentyl, cyclohexyl or cyclohexene group. -yl, otherwise for example optionally substituted phenyl or optionally substituted heteroaryl with 5-6 ring atoms including 1-3, especially 1-2 identical or different heteroatoms, such as in particular oxygen, nitrogen or sulfur, for example furan, thiophene, isoxazole or pyridine group. Distinctive substituents of the aromatic and heteroaromatic groups mentioned above as R2 are, for example, halogen, especially fluorine, chlorine or bromine; nitro group; straight alkyl group of 1-4 carbon atoms; an alkoxy or alkylthio group with 1-4 carbon atoms, for example a methoxy, ethoxy group or a methylthio, ethylthio or n-propylthio group; haloalkyl, haloalkoxy and haloalkylthio groups containing up to 4 carbon atoms and up to 8 halogen atoms, in particular fluorine and chlorine, for example trichloromethyl, trifluoromethyl or tetrafluoroethoxy; optionally substituted phenyl or phenylcarbonyl. R3 is especially hydrogen and a branched or unbranched alkoxy group with 1-4 carbon atoms, for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec- butoxy and tert-butoxy. R4 and R5 are for example an optionally substituted unbranched or branched alkyl group with up to 4 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, n-butyl or isobutyl. In addition, R4 and R5 together represent, for example, an alkylene group of 2 or 3 carbon atoms, which is optionally substituted with an alkyl group of up to 4 carbon atoms, for example a methyl or ethyl group. X is predominantly hydrogen, methyl, chlorine or bromine. The new N-substituted 2-methylnaphthylamides of the general formula I have a chilar hydrogen atom with a hydrogen atom, the group CH3, R1 and = N as ligands and, depending on the species R2, R3, R4 and R5, further chilarity centers. Optically pure enantiomers or diastereoisomers are obtained by conventional methods. The present invention includes a process for the preparation of these compounds both pure and in the form of mixtures. Pure enantiomers or uniform diastereoisomers as well as those usually obtained from the synthesis of mixtures are effective as fungicides. Moreover, it has been found that the novel compounds of general formula I are preferably prepared by preferably producing 2-methylnaphthylamine of general formula 2, wherein R 1 and X have the meanings given above, are reacted with an acid halide of the general formula R2 — CO — Hal or with an acid anhydride of the general formula R2 — CO — O — CO — R2, in which the formulas R2 has the meaning given above and Hal is a chlorine atom or bromine, the reactions being carried out at a temperature of -10-100 ° C, optionally in the presence of a solvent or diluent, optionally with the addition of an inorganic or organic base and optionally with the addition of a catalyst. Preferred, reagent-inert solvents or diluents are e.g., aliphatic or aromatic hydrocarbons such as pentane, cyclohexane, petroleum ether, benzene, toluene or xylenes; halogenated hydrocarbons, e.g. methylene chloride, chloroform, 1,2-dichloroethane or chlorobenzene; ketones such as acetone and methyl ethyl ketone; ethers, such as diethyl ether, dimethoxyethane, tetrahydrofuran or dioxane; esters such as ethyl acetate; nitriles such as acetonitrile; sulfoxides, such as dimethylsulfoxide, or suitable mixtures. Suitable inorganic or organic bases, which may be used in the reaction and also as acid binders, are, for example, alkali metal and alkaline earth metal carbonates, such as sodium or potassium hydrogen carbonate, sodium or potassium carbonate, carbonate calcium; borates, such as sodium borate; phosphates such as disodium or trisodium phosphate or dipotassium or tripotassium phosphate or amines such as triethylamine, N, N-dimethylaniline, N, N-dimethylcyclohexylamine, N-methylpiperidine or pyridine. Usually other bases can also be used. Catalysts include, in particular, metal halides, such as sodium bromide or potassium iodide, azoles, such as imidazole or 1,2,4-triazole, or pyridines, such as 4-dimethylaminopyridine. The reaction according to the invention is carried out, for example, at a temperature of -10- + 100 ° C, especially at a temperature of 0- + 40 ° C, under normal or increased pressure, in a continuous or periodic, continuous or periodic manner. Moreover, it has been found that the compounds of general formula 1 are prepared in this way the way that from 2-methylnaphthylamide of general formula Ia, in which R2 and X have the above meanings, and R4 and R5, independently of each other, represent an optionally substituted alkyl group with 1-4 carbon atoms, by cleavage of R4 and R5 the corresponding aldehyde is obtained or by reactions with a diol of the formula HO — R4 — R5 — OH, in which R4 and R5 together represent an alkylene group, the corresponding cyclic acetal is obtained, the reactions being optionally carried out in the presence of a dilute and optionally with the addition of an acid catalyst. The diols mentioned are, for example, 1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, 2,3-butanediol and 2,2-dimethyl-1,3-propanediol. The cleavage of R4 and R5 is carried out, for example, by the action of catalytic amounts of strong protic acids or Lewis acids such as hydrogen chloride or hydrochloric acid, hydrogen bromide, p-toluenesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, zinc chloride, zinc ethers. boric acid at a temperature from 0 ° C to the boiling point of the alcohols R4-OH and R5-OH which are split off. Reactions with 1,2- or 1,3-diol are carried out, for example, by removing the alcohols R4-OH and R5-OH from the reaction mixture by distillation under reduced or atmospheric pressure, or with an inert gas such as nitrogen or argon . Suitable solvents or diluents are the above-mentioned liquids, or water, or even 1,2 or 1,3-diols when using stoichiometric amounts or in excess. Lewis or protic acids, for example BF3, are used as acid catalysts. AlCh or ZnCU or mineral or sulphonic acids. Compounds of general formula I are also obtained by the fact that 2-methylnaphthylamide of general formula Ib, in which R1 and X have the above meanings, and Hal is a halogen atom, and R6 represents a hydrogen atom, an alkyl group of 1-3 carbon atoms, an alkenyl group of 2-4 carbon atoms, a cycloalkyl group of 3-7 carbon atoms or an alkoxy group of 1-5 carbon atoms, reacted with a nucleophilic compound of the general formula NuH wherein Nu is an alkoxy group of 1-5 carbon atoms or an alkylthio group of 1-4 carbon atoms, or a 1-imidazolyl, 1-pyrazolyl group or a 1,2,4-triazol-1-yl group, the reactions being carried out by possibly dissolves in the presence of of a solvent or diluent, optionally in the presence of an inorganic or organic base and optionally with the addition of a catalyst, at a temperature of -10 ° C + 100 ° C. The further compounds of general formula I are prepared in such a way that, depending on the functional species R1 and R2, there are usually chemical reactions. 2-methylnaphthylamines of general formula II, used as starting materials for the preparation of compounds of general formula I, are obtained by reacting 2-methylnaphthylamines of general formula III, in which X is as defined above, with an ester 2-halopropionic acid of general formula CH3 — CH (Hal) —COOCi — C4 — Alkyl, in which Hal is chlorine or bromine, or with a 2-halopropanal dialkyl acetal of general formula CH3 — CH (Hal) —CH (OR4) —OR5, where Hal is chlorine or bromine, and R4 and R5 are as defined above, optionally in the presence of a solvent or diluent, optionally in the presence of an inorganic or organic base and optionally with the addition of a catalyst, at a temperature of -10- + 130 ° C The above-mentioned compounds belong to the outstanding solvents and diluents, to the inorganic or organic bases and to the catalysts. It was further stated that the compounds of general formula II were obtained by giving 2-methylnaphthylam ine of the general formula III is reacted with a pyruvic acid ester of the general formula CH3-CO-COOCi-C4-Alkyl or with a methylglyoxal acetal of the general formula CH3-CO-CH (OR4) -OR5, in which R4 and R5 may be the meanings given above, and the Schiff base obtained as a reaction product is hydrogenated, e.g. with complex metal hydrides or catalytically with hydrogen. The preparation of the Schiff base is carried out, for example, by reacting 1 mole of 2-methylnaphthylamine of the general formula 3 from 0.9-1.5 mol of a pyruvic ester of the general formula CH3 — CO — COOCj — C4 — Alkyl or of a methylglyoxal acetal of the general formula CH3 — CO — CH (OR4) —OR5, the reactions being carried out in a solvent The water is separated off by distillation, optionally with the addition of an acid catalyst and at a temperature of 40-200 ° C., in particular 50-120 ° C. For the reaction, solvents which are inert under the reaction conditions and simultaneously form azeotropic mixtures with water are preferably used. Suitable solvents are, for example, aromatic hydrocarbons, for example benzene, toluene, ethylbenzene, o-, m-, and p-xylene, isopropylbenzene or methylnaphthalene; aliphatic or cycloaliphatic hydrocarbons, for example heptane, nonane, pinane, gasoline fractions boiling at 70-190 ° C, cyclohexane, methylcyclohexane, decalin, ligroin, 2,2,4-trimethylpentane, 2,2,3-trimethylpentane , 2,3,3-trimethylpentane, octane and the corresponding mixtures. Hydrogenation is carried out both by reduction with complex hydrides as well as by sodium boron hydride and by catalytic hydrogenation with hydrogen. Reduction with sodium boron hydride is generally carried out in this way that 1 mole of Schiff's base is reacted with 0.2-1 mole of sodium boron hydride in a solvent at a temperature of -20- + 40 ° C. In the catalytic hydrogenation, such amounts are introduced into the reaction mixture initially and during the reaction. hydrogen so that at the reaction temperature a suitable pressure is constantly maintained, preferably 15-30MPa. The reactions are generally carried out at a temperature of 20-200 ° C., in particular 25-160 ° C., batchwise or continuously. Inert gases such as nitrogen are optionally also used to set a suitable pressure. Solvents or diluents for both hydrogenation variants are suitable. alkanols and cycloacanols, e.g. n-propanol, isopropanol, n-butanol, isobutanol, glycol, ethylene glycol monoethyl ether, glycerin, amyl alcohol, cyclohexanol, 2-methyl-4-pentanol, 2-ethylhexanol, and especially methanol work particularly well and ethanol; cyclic ethers such as tetrahydrofuran and dioxane. For the catalytic hydrogenation, the catalyst is generally used in an amount of 5-30% by weight, based on Schiff's base. The catalyst is optionally used in a mixture with a carrier suitable for the reaction, e.g. silicon dioxide, the catalyst preferably being used in an amount of 10-40% by weight of the catalyst-carrier mixture. The catalysts are preferably copper chromin, e.g. cupric chromium oxide. as used by H. Adkins copper chromates, e.g., Houben-Weyl, Methoden der organischen Chemie, Vol. 4/2, pages 180-183 and J. Applied Chem. 5, 289-295 (1955). They contain, for example, copper-chromium spinel (CuCr204) or mixtures in the ratio 5CuO: 4Cr203 or are derived from such compounds, and may also contain other oxides, the main alkaline earth metal oxides such as magnesium, calcium or barium. The following descriptions explain the preparation of 2-methylnaphthylamines. of general formula 2. a) Direct alkylation of l-amino-2-methylnaphthalene according to scheme 1 144.2 g (0.92 mol) of l-amino-2-methylnaphthalene, 90.2 g (1.08 mol) of sodium bicarbonate and 460 g (2.76 mol) of 2-bromopropionic acid methyl ester is stirred for 18 hours at a temperature of 120-125 ° C. After cooling, the precipitate is filtered off under reduced pressure, and the filtrate is concentrated under reduced pressure. The residue is distilled under reduced pressure and thus obtaining 188 g, corresponding to 83.7% of theory, of N- (2-methyl-1-naphthyl) -alanine methyl ester as a colorless oil, bp 138-140 ° C / 20 Bye. b) Preparation of Schiff's base of 1-amino-2-methylnaphthalene according to scheme2 314 g (2 moles) of l-amino-2-methylnaphthalene, 232 g (2 moles) of pyruvic acid ethyl ester and 0.4 g of p-toluenesulfonic acid in 1000 ml of cyclohexane is boiled for 4 hours under reflux until 36 g of water are azeotroped and separated from the distillate. The cyclohexane is then distilled off under reduced pressure and the residue is directly reacted further. Yield of Schiff's base: 494.7 g corresponding to 97% of theory; according to scheme 3, 314 g of 1-amino-2-methylnaphthalene, 236 g of methylglyoxal dimethyl acetal and 0.4 g of p-toluenesulfonic acid are reacted in the same way as according to scheme 2. Yield of Schiff's base: 493.4 g, corresponding to 96% of theoretical yield. c) Hydrogenation of Schiff's base Cata lytic hydrogenation according to scheme 4 200 g of Schiff's base, made of 1-amino-2-methylnaphthalene and pyruvic acid ethyl ester, dissolved in 500 parts of tetrahydrofuran and 15 parts, are placed in a hydrogenation autoclave with a capacity of 11. Adkins catalyst (copper chromate powder). The autoclave is then heated to 150 ° C. and hydrogen is introduced until a pressure of 20 MPa is obtained. After approximately 9 hours, the hydrogen absorption is complete and the pressure is applied continuously. The reaction mixture is then cooled, the catalyst is filtered off under reduced pressure and the filtrate is concentrated also under reduced pressure. 142 g, corresponding to 71% of theory, of N- (2-methyl-1-naphthyl) -alanine ethyl ester are obtained as a colorless oil, boiling point 144-145 ° C / 15Pa. Reduction in sodium hydride with sodium hydroxide 490 g of Schiff's base , obtained from 1-amino-2-methyl naphthalene and methylglyoxal dimethyl acetal, is dissolved in 1500 ml of methanol and 60 g of sodium boron hydride are added portionwise to this solution at 0 ° C. It is stirred overnight, then methanol is distilled off, the residue is dissolved in 1000 ml of methylene chloride and stirred for 30 minutes with 500 ml of 10% potassium liquor, then the organic phase is separated and washed 3 times with water, using 200 ml each time, and then dried over sodium sulphate, methylene chloride is distilled off and the residue is distilled under reduced pressure. 367 g, corresponding to 74% of theory, of 2- (N-2'-methyl-1'-naphthyl) -aminopropanal dimethyl acetal with a boiling point of 140-145 ° C / 30Pa are obtained. Preferred compounds of the general formula 1 the following is mentioned: N - / (1-pyrazolyl) -acetyl) -N- (2'-methyl-1'-naphthyl-alanine methyl ester, N - (] - pyrazolyl) -acetyl / -N- ethyl ester (2l-methyl-1-naphthyl) -alanine, N - / (1,2,4-triazol-1-yl) -acetyl) -N- (2, -methyl-1-naphthyl) -alanine methyl ester, ester N - / (1,2,4-triazol-1-yl) -acetyl) -N- (2'-methyl- (1'-naphthyl) -alanine ethyl, N-cyclopropylcarbonyl-N- (2-methyl) methyl ester -1-naphthyl) -alanine, N-cyclopropylcarbonyl-N- (2-methyl-1-naphthyl) -alanine ethyl ester, N-cyclopentylcarbonyl-N- (2-methyl-1-naphthyl) -alanine methyl ester, methyl ester N-cyclohexylcarbonyl-N- (2-methyl-1-naphthyl) -alanine, N-methoxycarbonyl-N- (2-methyl-1-naphthyl) -alanine methyl ester, N-ethoxycarbonyl-N- (2-methyl) methyl ester -1-naphthyl) alanine, N-ethoxy ethyl ester rbonyl-N- (2-methyl-1-naphthyl) -alanine, N-propoxycarbonyl-N- (2-methyl-1-naphthyl) -alanine methyl ester, N-allyloxycarbonyl-N- (2-methyl-1) methyl ester -naphthyl) -alanine, N-butoxycarbonyl-N- (2-methyl-1-naphthyl) -alanine methyl ester, N-methoxalyl-N- (2-methyl-1-naphthyl) -alanine methyl ester, N- methyl ester ethoxyalyl-N- (2-methyl-1-naphthyl) -alanine, N-ethoxalyl-N- (2-methyl-1-naphthyl) -alanine ethyl ester, N-acetoacetyl-N- (2-methyl-1-methyl ester) -naphthyl) -alanine, N- (4-oxopentanoyl) -N- (2'-methyl-1'-naphthyl) -alanine methyl ester, N- (3-hydroxybutyryl) -N- (2'-methyl-) r-naphthyl) -alanine, N-benzoyl-N- (2-methyl-1-naphthyl) -alanine methyl ester, N- (2-chlorobenzoyl) -N- (2'-methyl-1'-naphthyl) methyl ester -alanine, N- (2-bromobenzoyl) -N- (2, -methyl-1'-naphthyl) -alanine methyl ester, N- (2-iodobenzoyl) -N- (2'-methyl-1 '- methyl ester naphthyl) -alanine, N- (2-methylbenzoyl) -N- (2'-methyl-1'-naphthyl) -alanine methyl ester, 6 123432 N - 4 -trifl methyl ester oromethylbenzoyl- Ny-methyl-1'-naphthyl) -alanine, N- (2-methoxybenzoyl) -N- (21-methyl-1'-naphthyl- alanine methyl ester, N - 4 -thiophenecarbonyl ^ N- ^ Z methyl ester -methyl-1'-naphthyl-alanine, N- (2-furancarbonyl) -N- (2, -methyl-r-naphthyl) -alanine methyl ester, N- (2-furancarbonyl) ethyl ester - N- (2 , methyl-1'-naphthyl) -alanine, N- (2-methylfuran-3-carbonylohN- (2'-methyl-1'-naphthyl) -alanine methyl ester, N- (2,5-dimethylturan-3- methyl ester) carbonyl) -N- (2, -methyl-1, -naphthyl) -alanine, N- (2,4,5-trimethylfuran-3-carbonyl) -N- (2, -methyl-1-naphthyl) methyl ester - alanine, N- (3-isoxazolylcarbonyl) -N- (2'-methyl-1'-naphthyl) -alanine methyl ester, N- (3-isoxazolylcarbonyl) -N- (2'-methyl-1'-naphthyl) ethyl ester ) -alanine, N- (3-methylisoxazolyl-5-carbonyl) -N- (2'-methyl-] '-naphthyl) -alanine methyl ester, N-nicotinoyl-N- (2-methyl-] - naphthyl methyl ester ) -alanine, N- (2-chloronicotinoyl) -N- (2, -methyl-1'-naphthyl) -alanine methyl ester, N-acryloyl-N- (2-methyl-1-na methyl ester) phthyl) alanine, N- (2-methylacryloyl) -N- (2, -methyl-1, -naphthyl) -alanine methyl ester, N-phenoxycarbonyl-N- (2-methyl-1-naphthyl) methyl ester -alanine, N- (4-chlorophenoxycarbonyl) -N- (2'-methyl-] '-naphthyl) -alanine methyl ester, 2- (N- (2-methyl-1-naphthyl) -N-acetyl dimethyl acetal) -aminopropanal, 2- (N- (2-methyl-1-naphthyl) -N-propionyl) -aminopropanal dimethyl acetal, 2- / N- (2-methyl-1-naphthyl) -N-butyryl / aminopropanal dimethyl acetal , 2- (N- (2-methyl-1-naphthyl) -N-chloroacetyl) -aminopropanal dimethyl acetal, N- (1- (]), 3'-dioxolan-2, -yl) -ethylAN- (2, , -methyl-r, -naphthyl) -amide of chloroacetic acid, N- (1- (4, -methyl-r, 3, -dioxolan-2, -yl) ethyl) -N- (2, -methyl) chloroacetic acid r, -naphthyl) -amide, 2- (N- (2-methyl-1-naphthyl) -N-bromoacetyl) -aminopropanal dimethyl acetal, 2- (2-methyl-J-) dimethyl acetal naphthyl) -N-iodoacetyl) -aminopropanal, 2- (N- (2-methyl-1-naphthyl) -N-methoxyacetyl) -aminopropanal dimethyl acetal, N- (1, 3, -2-dioxolane, -yl) -ethyl) -N- (2 "-methyl ol, - naphthyl) -amide, methoxyacetic acid, N- (1- (4'-methyl-1, 3'-dioxolan-2, -yl) -ethyl) -N- (2'-methyl-1, - naphthyl) -amide, methoxyacetic acid, N- (1- (4,5, -dimethyl-1,3,3-dioxolan-2, -yl) -ethyl) -N- (2 "-methyl) -naphthyl) -aniide of methoxyacetic acid, -naphthyl) -N-ethoxycarbonyl-aminopropanal, -naphthyl) -N-methylthioacetyl) -aminopropanal, -naphthyl) -N- (2, -chloropropionyl)) -aminopropanal, -naphthyl ) -N- (1 M-midazolylacetyl) / - aminopropanal, -naphthyl) -N- (1'-pyrazolylacetyl) / - aminopropanal, -naphthylJ-N2, [beta] -triazol-r-ylacetyl-aminopropanal, -naphthyl) -N-cyclopropylcarbonyl / -aminopropanal, -naphthyl) -N-cyclohexylcarbonyl / -aminopropanal, -naphthyl) -N-methoxycarbonyl / aminopropanal, -naphthyl) -N-ethoxycarbonyl / -aminopropanal, -N-naphthyl) aminopropanal, -naphthyl) -N-allyloxycarbonyl / -aminopropanal, -naphthyl) -N-methoxalyl / -aminopropanal, -naphthyl) -N-ethoxalyl / -aminopropanal, -naphthyl) -N-acetoacetyl / -aminopropanal, N- (2) "- methyl-1" -naphthyl) amide acetoacetic acid, -naphthyl) -N- (3'-hydroxybutyryl) / - aminopropanal, -naphthyl) -N-benzoyl / -aminopropanal, -naphthyl) -N- (2'-chk) robenzoyl) / - aminopropanal, -naphthyl ) -N- (2'-bromobenzoyl) / - aminopropanal, 2- / N- (2-methyl dimethyl acetal 2- / N- (2-methyl dimethyl acetal 2- / N- (2-methyl- 2- / N- (2-methyl-dimethyl acetal 2- / N- (2-methyl dimethyl acetal 2- / N- (2-methyl dimethyl acetal) 2- / N- (2-methyl dimethyl acetal) dimethyl acetal 2- / N- (2-methyl-dimethyl acetal 2- / N- (2-methyl dimethyl acetal 2- / N- (2-methyl dimethyl acetal 2- / N- (2-methyl dimethyl acetal 2- / N- (2-Methyl dimethyl acetal 2- / N- (2-Methyl dimethyl acetal 2- / N- (2-Methyl dimethyl acetal 2- / N- (2-methyl-N-Zl-Cr) 2- / N- (2-Methyl dimethyl acetal 2- / N- (2-methyl dimethyl acetal 2- / N- (2-methyl dimethyl acetal 2- / N)) T-dioxolan-r-ylHtyl / dimethyl acetal - (2-methyl-123432 7 dimethyl acetal 2- (N- (2-methyl-1-naphthyl) -N- (2, -trifluoromethylbenzoyl)) - aminopropanal, dimethyl acetal 2 (N- (2-methyl-1-naphthyl) -N- (2, -methoxybenzoyl)) -aminopropanal, 2- (N- (2-methyl-1-naphthyl) dimethyl acetal) -N- (2 ' -furanocarbonyl) - aminopropanal, N- (1- (1,3, -dioxolan-2, -yl) -ethyl) -N- (2, -methyl-1,3-naphthyl) -amide 2- furanecarboxylic acid, 2- (N- (2-methyl-1-naphthyl) -N- (2, -methyl-furan-3'-carbonyl) - aminopropanal dimethyl acetal, 2- / N- dimethyl acetal ( 2-methyl-1-naphthyl) -N- (2, 4, 5, -trimethylfuran-3, -carbonyl) - amino-propanal, 2- (N- (2-methyl-1-naphthyl) dimethyl acetal) -N- (3Mzoxazolylcarbonyl) / - aminopropanal, 2- / N- (2-methyl-1-naphthyl-N-methyl-1-naphthyl-N-methyl-isoxazolyl-S-carbonyl-aminopropanal dimethyl acetal, 2- / N- (2- methyl-1-naphthyl) -N-nicotinoyl) - aminopropanal, 2- (N- (2-methyl-1-naphthyl) -N- (2-chloronicotinoyl) -aminopropanal dimethyl acetal, 2- (N) dimethyl acetal - (2-methyl-1-naphthyl) -N-acryloyl) -aminopropanal, 2- (N- (2-methyl-1-naphthyl) -N- (4, -chlorophenoxycarbonyl)) -aminopropanal dimethyl acetal, N methyl ester - (2-furanok arbonyl) -N- (2'-methyl-4, -bromo-1'-naphthyl) -alanine, N-methoxyacetyl-N- (2-methyl-4-bromo-1-naphthyl) -alanine methyl ester, 2- / N- (2-methyl-1-naphthyl) -N-bromoacetyl / -aminopropanal, 2- (N- (2-methyl-J-naphthyl) -N-methoxyacetyl / -aminopropanal. The following examples explain the preparation of new compounds according to The invention is not limited to the scope of the invention. Example I. Preparation of the compound of formula 4. A mixture consisting of 30.7 g (0.12 mol) of N- (2-methyl-1-naphthyl) -alanine methyl ester, 9.5 g ( 0.12 mol) of pyridine, 5 g of 4-dimethylaminopyridine and 50 ml of acetic anhydride are stirred at 80 ° C. for 8 hours, then cooled and concentrated under reduced pressure. 250 ml of diethyl ether and 250 ml of water are added to the residue. The organic phase is separated, washed with 100 ml of 1N hydrochloric acid and then with 100 ml of water, and then decolorized with carbon and concentrated. The residue is stirred at 0 ° C with 30 ml of a 5: 1 mixture of petroleum ether and diethyl ether and then left for 4 hours at 0 ° C to crystallize out. This gives 23.6 g, corresponding to 69% of theory, of N-acetyl-N- (2-methyl-1-naphthyl) -alanine methyl ester in the form of white crystals, m.p. 119-121 ° C. Example II. Preparation of the compound of formula 5. To a vigorously stirred suspension of 14 g (0.17 mol) of sodium bicarbonate and 20 g of sodium sulfate in 150 ml of dry toluene is added 19.4 g (0.09 mol) of N- (2-methyl-1) methyl ester. -naphthyl) -alanine and then a solution of 24.2 g (0.12 mol) of bromoacetyl bromide in 50 ml of toluene is added dropwise over 1 hour at + 15 ° C. The mixture is stirred for 5 hours at 25 ° C, then the precipitate is filtered off under reduced pressure and washed with 50 ml of toluene. The filtrate is washed twice with 1 N sodium hydroxide solution, using 100 ml each time, once with 50 ml of 2N hydrochloric acid and finally with 100 ml of water, dried, decolourised with carbon and concentrated under reduced pressure. The oily residue is dried for 3 hours at 50 ° C and a pressure of 10 Pa. This gives 22.5 g, corresponding to 77.3% of theory, of N-bromoacetyl-N- (2-methyl-1-naphthyl) -alanine methyl ester as a light yellow oil. IR spectrum (film): 3035, 2970, 2935 , 1730, 1652, 1440, 1415, 1360, 1200, 1132, 1095, 812, 782, 744 cm "1. Example III. Preparation of the compound of formula 6.1. 13 g (0.036 mol) of N-bromoacetyl-N- methyl ester (2- methyl-1-naphthyl) -alanine (Example 2) is dissolved in 60 ml of dry dimethylformamide and 6.8 g (0.1 mol) of imidazole are added. The mixture is stirred for 10 hours at 60 ° C and concentrated under reduced pressure. The residue is shaken with 150 ml of methylene chloride and 50 ml of water, the organic layer is stripped and washed twice with water, using 50 ml each time. The organic solution is dried, decolorized with carbon and concentrated. After purification of the crude product by filtering its solution in ethyl acetate through silica gel and concentration are obtained as residue 9.6 g of resin. 8 123432 Analysis: calculated: C 68.4 H 6.0 N 12.0% found no: C 68.0 H 6.4 N 11.9%. Example IV. Preparation of the compound of formula 7. To 24.3 g (OJ mole) of N- (2-methyl-1-naphthyl) -alanine methyl ester and 0.5 ml of triethylamine in 50 ml of dry toluene are added dropwise with stirring at 90 ° C 9 g (0.1 mol) of diketene. The mixture is stirred for 3 hours at 95 ° C, then cooled, washed once with 50 ml of 2N hydrochloric acid and once with water, dried and concentrated. The crude product is purified by filtering its ethyl acetate solution through silica gel and then the ethyl acetate is evaporated off to give 29.7 g (90% of theory) of the residue as analytically pure oil. IR spectrum (film): 3042 , 2980, 2940, 1740, 1720, 1650, 1650, 1455, 1370, 1310, 1195, 920, 815, 786, 746 cm _1. Example V. Preparation of the compound of formula 8, 22.2 g (0.066 mol) of methyl ester N- (2-furancarbonyl) -N- (2, -methyl-1-naphthyl) -alanine (example XXI) and 6 g (0.07 mol) of anhydrous sodium acetate in 150 ml of acetic acid, 11 g (0.067 mol) of bromine are added and it is stirred for 24 hours at 35 ° C. Then it is mixed with 700 ml of ice water and the product is extracted 3 times with ether, using 100 ml each time. The combined ether extracts are washed once with 100 ml of 1 N sodium hydroxide solution and once with water, dried and concentrated. This gives 17 g, or 62% of theory, of N- (2-furancarbonyl) -N- (2'-methyl-4'-bromo-r-naphthyl) -alanine methyl ester in the form of a colorless resin. IR spectrum (film ): 3035, 2930, 1730, 1640, 1450, 1360, 1235, 1190, 1126, 1092,908, 810 cm "1. Example VI. Preparation of the compound of formula 9. 14.2 g (0.04 mol) dimethyl acetal 2- (N- (2-methyl-1-naphthyl) -N- (2'-furancarbonyl)) -aminopropanal (Example XXIII) 3 ml of ethylene glycol and 0.2 g of p-toluenesulfonic acid in 80 ml of toluene are stirred at 80 ° C for 8 hours The methanol formed is continuously removed from the reaction mixture with a weak nitrogen stream After cooling and washing with water three times with 60 ml each, the organic solution is decolorized with carbon and concentrated. The residue crystallizes on adding 10 ml of cold ether. 9 g are obtained, corresponding to 64% of theory. naphthyl) amide of 2-furancarboxylic acid in the form white crystals with a melting point of 129-131 ° C. Example VII. Preparation of a compound of formula 10. Solution of 7.6 g (0.02 mol) of 2- (N- (2-methyl-1-naphthyl) -N-bromoacetyl) -aminopropanal dimethyl acetal (Example XII) in 50 ml of chloride methylene is stirred vigorously for 1 hour at room temperature with 100 ml of 2N hydrochloric acid. The organic phase is separated, washed with 100% water, dried and concentrated. This yields 5.3 g, corresponding to 80% of the theoretical yield of 2- (N- (2-methyl-1-naphthyl) -N-bromoacetylAaminopropanal as a light yellow oil. IR spectrum (film): 3038, 2970, 2820, 2710, 1720, 1645, 1490, 1365, 1203, 810, 778, 742, 640 cm "1. The compounds of the general formula I are prepared analogously, which are detailed in Table I. The new active substances have a strong fungicidal activity against fungi. Plant diseases, especially those of the class Phycomyceten, are therefore suitable, for example, for the control of fungi such as Phytophthora infestens on tomatoes and potatoes, Phytophthora parasitica on wild strawberries, Phytophthora cactorum on apples, Pseudoperonospora cubulospora on cucumbers. on hops, Peronosporadestructor on onion, Peronospora sparsa on roses, Peronospora tabacica on tobacco, Plasmopara viticola on grapevines, Plasmopara halstedii on sunflowers, Sclerospora on maize, Bremia lactocae on lettuce, M ucor mucedo on fruit, Rhizopus nigricans on turnips, Erysiphe graminis on cereal, Uncinula necator on grapevines, Podophaera leucotricha on apples, Sphaerotheca fuliginea on roses, Erysiphe cichoriacearum on cucumbers. The agent contains 0.1-95% by weight of the invention as a fungicide. , 5-90% by weight of the active ingredient. Depending on the desired effect, 0.1-5 kg of active ingredient per hectare are used. Some of the active ingredients of the agent according to the invention have medicinal properties, that is to say, in order to obtain a more reliable control effect, the active ingredients are applied even after the plant has been infected with germs. Good fungicidal activity is demonstrated by active substances with a particle size of not 5 /i. Moreover, many of the new active substances have a systemic effect that by treating the roots, it is also possible to protect above-ground plant parts. According to the invention, the active substances can be mixed and applied together with other active substances, e.g. with herbicides, insecticides, growth regulators and fungicides, or with fertilizers. When mixed with fungicides, the fungicidal range of action is in many cases extended. A number of these fungicidal mixtures also exhibit synergistic effects, that is, the fungicidal effectiveness of the combined product is greater than the sum of the effectiveness of the individual components. A particularly advantageous extension of the action range is achieved with fungicides such as: manganese ethylene bis-dithiocarbamate, manganese zinc ethylene bis-dithiocarbamate, zinc-ammonium N, N-ethylene bis-dithiocarbamate, N-trichloromethylthiotetra-trichloromethyl-trichloromethide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-methoxycarbonylaminobenzimidazole, 2-rhodanomethylthiobenzothiazole, J, 4-dichloro-2,5-dimethoxybenzene, 2,3-dichloro-6-methyl-1 acid anilide, 4-oxathiino-5-carboxylic acid, 2-methyl-5,6-dihydro-4-H-pyran-3-carboxylic acid anilide, 2,4,5-trimethylfuran-3-carboxylic acid anilide, 2-methylfuran- anilide 3-carboxylic acid, 2,5-dimethylfuran-3-carboxylic acid cyclohexylamide, 2,5-dimethylfuran-3-carboxylic acid N-cyclohexyl-N-methoxyamide, 5-methyl-5-vinyl-3- (3,5-dichlorophenyl) ) -2,4-dioxo-1,3-oxazolidine and 3- (3,5-dichlorophenyl) -5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione. The following list of fungal agents The active substances of the present invention may be mixed with which the active substances of the present invention may be mixed with, but not limited to, the possible combinations. The fungicides which may be mixed with the active substances of the present invention are, for example: dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, , zinc ethylene bis dithiocarbamate, tetramethylthiuram disulfide, zinc N, N-propylene bis dithiocarbamate, N, N'-propylene bis dithiocarbamate, zinc ammonium disulfide and N 1 N 2 polypropylene bis thiocarbamyl disulfide, such as - (1-methylheptyl) -phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropyl carboxylate, compounds with a heterocyclic structure such as 2-heptadecyl-2 -imidazolineacetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethylphthalimidothiophosphonate, 5-amino-J- (bis-dimethylamino-phosphinyl) -3-phenyl -], 2,4 -triazole, 2,3-dicyano-1,4-dithiaanthraquinone, 2-t io-1,3-dithio- (4,5-b) -quinoxaline, 1- (butylcarbamyl) -2-benzimidazolcarbamic acid methyl ester, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, 10 123 432 Pyridine-2-thiol 1-oxide, 8-hydroxyquinoline or its copper salts, 4,4-dioxide, 2,3-dihydro-5-carboxyanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5 -carboxyanilido-6-methyl-1,4-oxathiine, 2- (2-furyl) -benzimidazole, piperazin-1,4-diyl-bis-] - (2,2,2-trichloroethyl) -formamide /, 2 - (4-thiazolyl) -benzimidazole, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis- (p-chlorophenyl) -3-pyridinemethanol, 1,2-bis- (3-ethoxycarbonyl-2- thioureido) -benzene, 1,2-bis- (3-methoxycarbonyl-2-thioureido) -benzene and various fungicides, such as dodecylguanidine acetate, 3- (3- (3,5-dimethyl-2-oxycyclohexyl) -2) -hydroxyethyl-glutarimide, hexachlorobenzene, N-dichlorofluoromethylthio-N, N1-dimethyl-N-phenyldiamide of sulfuric acid, 2,5-dimethylfuran-3-carboxylic acid anilide, 2-methylbenzoic acid anilide, 2-acid anilide - iodobenzoic acid, 1- (3,4, -dichloroanilino) -1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, 1- (4-chlorophenoxy) -3,3- dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol and a- (2-chlorophenyl) -a- (4-chlorophenyl) -5-pyrimidinomethanol. The active substances of the agent according to the invention are used for example in the form of solutions, powders, suspensions suitable for direct spraying, also high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents or granules, by spraying, nebulizing, dusting, sprinkling, dressing or pouring. The form used depends entirely on the purpose of use and should in any case ensure the best possible distribution of the active substance. The particle size distribution can influence the effect of the active substance, namely it has been found that the increasing fineness of the active substance improves its fungicidal action. Mineral oil fractions with medium to high boiling point are used to prepare solutions, emulsions, pastes and oil dispersions suitable for direct spraying. , such as kerosene or diesel engine oil, furthermore coal tar oils, etc., as well as oils of vegetable and animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives , e.g. methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone etc., strongly polar solvents such as e.g. dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water etc. The aqueous forms of use are prepared by adding water to emulsion concentrates, pastes, powders, incl cyanotic or oil dispersions. In order to prepare emulsions, pastes or oil dispersions, the substances as such or dissolved in oil or solvents are homogenized in water with wetting, adhesion promoting, dispersing or emulsifying agents. It is also possible, if appropriate, to prepare concentrates suitable for diluting with water, consisting of active ingredient, wetting agent, adhesion promoter, dispersing or emulsifying agent, and possibly a solvent or oil. As surface-active substances, alkali metal, alkaline earth metal salts are used. and ammonium salts of lignin sulfonic acid, naphthalenesulfonic acids and phenolsulfonic acid, alkylarylsulfonates, alkanesulfonates, alkyl sulfates, metal salts 123,432 11 alkali and alkaline earth metals of dibutylnaphthalenesulfonic acid, sulfated ethoxylated lauryl alcohol, alkali metal sulfates, alkali metal salts of earth alcohol sulphated hexadecanols, heptadecanols and octadecanols, sulphated glycol ether and fatty alcohol salts, condensation products of sulphonated naphthalene and naphthalene derivatives with formaldehyde, con densation of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol and nonylphenol, polyglycol alkylphenol ethers, polyglycol tributylphenyl ether, alkylaryl polyethylene glycol ethoxylated alcohol products, ethoxylated alcohol ethoxylates, ethoxyl alcohol ethoxylates, ethoxylated alcohol ethoxylates polyoxyethylene, ethoxylated polyoxypropylene, polyglycol lauryl acetalether, sorbitol esters, lignin, sulfite lugs and methylcellulose Powders, dusting and dusting agents are prepared by mixing or jointly grinding the active substances with a solid carrier. Granules, e.g. impregnated granules, e.g. and homogeneous, are prepared by combining active substances with solid carriers such as e.g. mineral earth, such as silica gel, silicic acids, silica gels, silicates, talc, kaolin, Attaclay clay, limestone, chalk, bolus clay, loess, clay, dolomite, diat omit, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers such as ammonium sulphate, ammonium phosphate, ammonium nitrate, urea and plant products such as cereal flour, wood bark, wood and nut lupine flour, powdered cellulose and other solid carriers. The following compounds were used as known comparative active substances in the experiments presented below: N-trichloromethylthiophthalimide - compound A N-trichloromethylthiotetrahydrophthalimide - compound B zinc ethylene-1,2-bis-dithiocarbamate - compound C. Experiment 1. Action 1. east on peas. 100 g of a sample of pea seeds of the 'Senator44' variety were mixed for about 5 minutes in glass bottles with 300 mg, corresponding to 0.3% by weight, of preparations for dressing, containing 40% of active substance in dry matter. Then 100 seeds from each sample were sown to a depth of 3 cm at intervals of 3-5 cm in boxes filled with compost soil that showed a strong natural fungus contamination by Pythium spec, Aphanomyces spec. and Fusarium oxysporum. The boxes were placed in a greenhouse at 17-20 ° C. After 21 days, the number of healthy pea plants was determined. The results of the experiment are presented in Table II. Experience?,. Effects against Erysiphe graminis in wheat. Leaves of wheat seedlings growing in pots, cv. "Jubilar", were sprayed with aqueous suspensions composed of 80% (weight percent) of the active ingredient and 20% emulsifier. After the spray coating had dried on, the plants were dusted with spores of wheat powdery mildew (Erysiphe graminis var. Tritepalne rosliny). was set in a greenhouse at a temperature of 20-22 ° C and a relative air humidity of 75-80%. After 10 days, the extent of the development of the mildew fungus was assessed. The results obtained are presented in Table III. Experiment 3. Action against Phytophthora infestans on tomatoes. Leaves growing in Pots of tomato plants of the cultivar "Grosse Fleischtomate" were sprayed with aqueous suspensions containing 0.025% (weight percent) of the active ingredient. After the spray coating had dried on, the leaves were contaminated with a spore suspension of Phytophthora infestans. The plants were then placed in a chamber with saturated steam at 16-18 ° C. After 5 days on untreated but contaminated control plants, the disease developed so strongly that it was possible to evaluate the fungicidal activity of the test substances. The results obtained are presented in Table IV. Experiment 4. Action against Plasmopara viticola on grapevines. Leaves of potted grapevines of the cultivar "Muller-Thurgau" were sprayed with aqueous suspensions containing 0.025% (weight percent) of the active ingredient. In order to evaluate the duration of action of the active ingredients, the plants were placed in a greenhouse for 10 days after drying. leaves suspension of the spore of the fungus Plasmopara viticola, and then the plants were placed first for 16 hours in a saturated steam chamber at 24 ° C, and then for 8 days in a greenhouse at 20-30 ° C. After this time, to accelerate When the spore stems break out, the plants are returned to the steam-saturated chamber for 16 hours. Then the development of the fungus on the lower side of the leaves is assessed. The results are presented in Table V. Below are examples of preparation of preparations.I. 90 parts by weight in relation to Example I is mixed with 10 parts by weight of N-methyl-α-pyrrolidone and thus a solution suitable for the stack is obtained. very fine droplets. II. 10 parts by weight of the compound of Example II are dissolved in a mixture of 90 parts by weight of xylene, 6 parts by weight of the addition product, 8-10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 2 parts by weight of dodecylbenzenesulfonic acid calcium salt and 2 parts by weight of the product of the addition of 40 moles of ethylene oxide to 1 mole of castor oil. III. 20 parts by weight of the compound of Example III is dissolved in a mixture of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the product of adding 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient. IV. 20 parts by weight of the compound of Example 1 are dissolved in a mixture of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210-280 ° C and 10 parts by weight of the product of combining 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient. 80 parts by weight of the compound of Example II are thoroughly mixed and ground in a hammer mill with 3 parts by weight of diisobutylnaphthalene-a-sulfonic acid sodium, 10 parts by weight of sodium ligninsulfonic acid with sulfite liquor and 7 parts by weight of powdered silica gel. By dispersing this mixture in water, a spray liquid is obtained. VI. The 3 parts by weight of the compound of Example III are mixed with exactly 97 parts by weight of finely ground kaolin. This produces a dust containing 3% by weight of active ingredient. VII. 30 parts by weight of the compound of Example 1 are mixed intimately with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of the gel. This gives an active ingredient formulation with good adhesion. VIII. 40 parts by weight of the compound of Example 2 are mixed intimately with 10 parts of the sodium salt of the phenol sulfonic acid urea formaldehyde condensate, 2 parts of silica gel and 48 parts of water. Thus, a stable water dispersion is obtained. By diluting it with 100,000 parts by weight of water, an aqueous dispersion is obtained containing 0.04% by weight of the active ingredient. The 20 parts of the compound of example III are mixed exactly with 2 parts of calcium dodecylbenzene sulphonic acid, 8 parts of fatty alcohol and polyglycol ether, 2 parts of sodium phenolsulphonic acid urea formaldehyde condensate and 68 parts of paraffinated mineral oil. Thus, a stable oil dispersion is obtained. PL

Claims (1)

Zastrzezenie patentowe Srodek grzybobójczy, zawierajacy staly albo ciekly nosnik oraz substancje czynna, znamienny tym, ze jako substancje czynna zawiera N-podstawiony 2-metylonaftyloamid o wzorze ogólnym 1, w którym R1 oznacza grupe o wzorze —CO—R3, przy czym R3 oznacza atom wodoru albo grupe123432 13 alkoksylowa o 1-4 atomach wegla, i dalej Rl oznacza grupe o wzorze —CH(OR4)—OR5, przy czym R4 i R5 niezaleznie od siebie oznaczaja ewentualnie podstawiona grupe alkilowa o 1-4 atomach wegla albo R4 i R5 razem oznaczaja grupe alkilenowa, która razem z grupa, do której jest podstawiona, tworzy ewentualnie podstawiony przez grupe alkilowa o 1-4 atomach wegla albo przez grupe arylowa 5- lub 6-czlonowy pierscien heterocykliczny, zawierajacy 2 atomy tlenu, a R2 oznacza grupe alkilowa o 1-4 atomach wegla, która jest ewentualnie podstawiona atomem fluoru, chloru, bromu lub jodu, grupe alkoksylowa o 1-4 atomach wegla, grupa alkilotio o 1-4 atomach wegla, grupa 1-idmidazolilowa, 1-pirazolilowa. 1,2,4-triazol-l-ilowa albo grupa keto, dalej R2 oznacza grupe alkenylowa o 2-5 atomach wegla, grupe alkinylowa o 2-5 atomach wegla, grupe cykloalkenylowa o 3-7 atomach wegla, grupe alkoksylowa o 1-5 atomach wegla, ewentualnie podstawiona grupe fenylowa albo ewentualnie podstawiona grupe heteroarylowa, zas X oznacza atom wodoru, grupe metylowa, atom chloru albo bromu. Przy¬ klad nr 1 VIII IX X XI XII XIII X 2 H H H H H H R1 3 —CH(OCH3)2 —CH(OCH3)2 —COOCH3 —CH(OCH3)2 —COOCH3 —CH(OCH3)2 Tablica R2 4 —CH3 -C2Hj —CH^Cl —CHzCl —O—CH3 —CH2Br I Temperatu¬ ra topnie¬ nia^ 5 olej olej olej 80-82 zywica zywica Widmo IR (film) (cm"') 6 3042,2980,2930,1645, 1448,1360,1295,1148, 1120,1062,945,814, 786,747 2972,2928,1642,1445, 1365,1256,1120,1080, 1060,952,811,783,744 3042,2980,2940,1740, 1622,1505,1365,1240, 1200,1105,1050,815, 783,748 3040,2940,2910,1732, 1690,1430,1325,1190, 1066,1025,810,785, 772,742 3018,2912,2810,1645, 1585,1556,1415,1256, 1235,1138,1085,810, 780, XIV H —COOCH3 XV H —COOCH3 XVIII H wzór 11 XIX H —COOCH3 —C2H 2n5 olej CH2—O—CH3 CH2—O—CH3 CH2—S—CH3 olej 107-109 olej 3045,2972,1720,1648, 1440,1390,1260,1170, 1130,1075,812,780,644 3042,2935,1732,1664, 1440,1380,1280,1190, 1125,812,784,746 3035,2975,2935,1730, 1640,1440,1359,1210, 1185,1100,1043,978, 810,780,74414 123432 1 XX XXI 2 H H 3 —COOCH3 —COOCH3 wzór wzór 12 13 4 5 106-108 olej 6 3040,2.980,2938,2938, 1712,1630,1548,146, 1400,1304,1246,1190, 1098,1010,814,780, 762 XXII H —COOC2H5 XXIII H XXIV H —COOCH3 XXVI H —COOCH3 XXVII H —COOCH3 wzór 13 -CH(OCH3)2 wzór 13 wzór 14 XXV H —CH(OCH3)2 wzór 15 wzór 16 wzór 17 olej 3130,2982,2935,2900, 1710,1630,1550,1450, 1402,1302,1240,1095, 1070,812,7... 760 olej 2968,2925,1625,1555, 1455,1376,1305,1174, 1100,1058,810,795, 779,750 zywica 3108,3038,2935,1726, 1635,1532,14.., 1330, 1200,1100,1042,875, 856,810,796,778,758, 742 zywica 3105,3040,2930,1640, 1544,1438,180., 1200, 1100,1058,835,810, 795,778,75., 743 zywica 3038,2970,2935,2908, 1725,1615,156., 1420, 1310,1292,1200,1130, 1022,810,782,763,745 zywica 3030,2932,1728,1640, 1560,1430,1135,1290, 1210,1188,810,779,745 Tablica II Substancja czynna (preparat do zaprawiania) z przykladu nr Zdrowe rosliny po 21 dniach w ziemi kompostowej % II X XVI XIX XX xxi Zwiazek B (srodek porównawczy) Kontrola (nie traktowana) zakazona ziemia kompostowa Kontrola (nie traktowana) sterylizowana ziemia kompostowa 86 84 92 90 88 85 70 18 92123432 Tablica III Substancja czynna z przykladu nr V VIII XII XVI XXVI Kontrola (nie traktowana) Porazenie lisci po opryskan zawierajaca 0,05 0 1 0 0 1. Iu ciecza substancje czynna (%) 0,025 2. 1 0 1 1 5 0,012 4 3-4 0 3. -4 1 0 = brak porazenia grzybem, stopniowo do 5 = calkowite porazenie Tablica IV Substancja czynna Porazenie lisci po opryskaniu ciecza z przykladu nr zawierajaca 0,025% substancji czynnej IV 0 VIII 0 XVII 1 XX 0 XXI 1-2 XXIV 1 Zwiazek C (srodek porównawczy) 2-3 Kontrola (nietraktowana) 5 0 = brak porazenia grzybem, stopniowo do 5 = calkowite porazenie Tablica V Substancja czynna Porazenie lisci po opryskaniu ciecza z przykladu nr zawierajaca 0,025% substancji czynnej X 0 XXI 0 Zwiazek A (srodek porównawczy) 2 Kontrola (nie traktowana) 5 0 = brak porazenia grzybem, stopniowo do 5 = calkowite porazenie123432 CH, X- X- CH3 CH_R1 O c-r2 0 WZOR 1 / CH, 0R CH, I 3 / 1 J /CH-CH 5 i"R 0 WZOR la CH3 ?H3 , CH-R1 X^(( )-n' ,R X-CH^ Jl \ 0 Hal WZOR 1 b CH^ NH- WZÓR 3 CH: 9H3 3 /CH- COOCHo O C0-CH3 :H3 XH-CCOCH, (C\ XO-CH2-Br WZOR 4 WZOR 5 CH3 CH3 CH-COOCH3 M xco-ch2-nTj WZOR 6 CH CH: I * 3 CH-COOCH3 CH- s' V CH< WZOR 7123432 CH- H: Br N XH-COOCH3 \;o-^V WZÓR 8 CHo I O CH3 CH_cA-pH2 tTCH2 OK WZÓR 9 CH- CH- '3 CH-CHO (^ CO-CH2Br WZÓR 10 -s WZÓR CH2- N j N 11 WZÓR 12 ^ WZÓR 13 -O) N WZÓR U ^° WZÓR 15 CH. WZÓR 16 -SvN CH3 WZÓR 17123432 NH- OorCH\ I 3 Br-CH-COOCH- I 3 Mu CH-COOCH-, NH i J HBr do ¦CH3 SCHEMAT 1 NH2 H- QQf * CH3-CD-COOC2H5 ^ QO CH3 n = c-cooc2h5 CH-, SCHEMAT 2 CH3 NH- H^ POT ?CHjCO-CH(OCH^2 -^— Q^ N = C-CHfOCH^2 CH3 SCHEMAT 3 CH3 N = C- CH: COOC^Hg CH3 NH-CH-COOCjHj -OÓrCH3 SCHEMAT 4 Pracownia Poligraficzna UP PRL. Naklad 100 cgz. Cena 100 zl PLClaim A fungicide containing a solid or liquid carrier and an active ingredient, characterized in that the active ingredient is an N-substituted 2-methylnaphthylamide of the general formula I, in which R1 represents a group of the formula —CO — R3, where R3 is an atom hydrogen or 12343213 alkoxy group with 1-4 carbon atoms, and hereinafter Rl represents a group of formula -CH (OR4) -OR5, where R4 and R5 independently of each other represent optionally substituted alkyl group with 1-4 carbon atoms or R4 and R5 together represent an alkylene group which, together with the group to which it is substituted, forms optionally substituted by an alkyl group of 1-4 carbon atoms or by an aryl group of a 5- or 6-membered heterocyclic ring containing 2 oxygen atoms, and R2 is an alkyl group with 1-4 carbon atoms which are optionally substituted with fluoro, chloro, bromo or iodo, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, 1-id-idazolyl, 1-pyrazolyl. 1,2,4-triazol-1-yl or a keto group, further R2 is an alkenyl group of 2-5 carbon atoms, an alkynyl group of 2-5 carbon atoms, a cycloalkenyl group of 3-7 carbon atoms, an alkoxy group of 1- 5 carbon atoms, an optionally substituted phenyl group or an optionally substituted heteroaryl group, and X is hydrogen, methyl, chlorine or bromine. Example No. 1 VIII IX X XI XII XIII X 2 HHHHHH R1 3 —CH (OCH3) 2 —CH (OCH3) 2 —COOCH3 —CH (OCH3) 2 —COOCH3 —CH (OCH3) 2 Table R2 4 —CH3 - C2Hj —CH2Cl —CH2Cl —O — CH3 —CH2Br I Melting point ^ 5 oil oil oil 80-82 resin resin IR spectrum (film) (cm ") 6 3042, 2980, 2930, 1645, 1448 , 1360,1295,1148, 1120,1062,945,814, 786,747 2972,2928,1642,1445, 1365,1256,1120,1080, 1060,952,811,783,744 3042,2980,2940,1740, 1622,1505,1365,1240, 1200 , 1105,1050,815, 783,748 3040,2940,2910,1732,1690,1430,1325,1190,1066,1025,810,785, 772,742 3018,2912,2810,1645, 1585,1556,1415,1256, 1235,1138 , 1085.810, 780, XIV H —COOCH3 XV H —COOCH3 XVIII H formula 11 XIX H —COOCH3 —C2H 2n5 oil CH2 — O — CH3 CH2 — O — CH3 CH2 — S — CH3 oil 107-109 oil 3045.2972 , 1720,1648, 1440,1390,1260,1170, 1130,1075,812,780,644 3042,2935,1732,1664, 1440,1380,1280,1190, 1125,812,784,746 3035,2975,2935,1730, 1640,1440,1359 , 1210, 1185,1100,1043,978, 810,780,74414 123432 1 XX XXI 2 HH 3 —COOCH3 —COOCH3 formula formula 12 13 4 5 106-108 oil 6 3040.2. 980,2938,2938,1712,1630,1548,146, 1400,1304,1246,1190, 1098,1010,814,780, 762 XXII H —COOC2H5 XXIII H XXIV H —COOCH3 XXVI H —COOCH3 XXVII H —COOCH3 formula 13 - CH (OCH3) 2 formula 13 formula 14 XXV H —CH (OCH3) 2 formula 15 formula 16 formula 17 oil 3130,2982,2935,2900,1710,1630,1550,1450, 1402,1302,1240,1095, 1070, 812.7 ... 760 oil 2968.2925.1625.1555, 1455.1376.1305,1174, 1100.1058.810.795, 779.750 resin 3108.3038.2935.1726, 1635.1532.14 .., 1330, 1200,1100,1042,875, 856,810,796,778,758, 742 resin 3105,3040,2930,1640,1544,1438,180., 1200, 1100,1058,835,810, 795,778.75., 743 resin 3038,2970,2935,2908, 1725,1615,156., 1420, 1310,1292,1200,1130, 1022,810,782,763,745 resin 3030,2932,1728,1640,1560,1430,1135,1290, 1210,1188,810,779,745 Table II Active substance (preparation for dressing ) of example No. Healthy plants after 21 days in compost soil% II X XVI XIX XX xxi Compound B (comparative measure) Control (untreated) contaminated compost soil Control (untreated) sterilized soil compost 86 84 92 90 88 85 70 18 92123432 Table III Active substance of the example no. V VIII XII XVI XXVI Control (not treated) Infection of leaves after spraying containing 0.05 0 1 0 0 1. Iu liquid active substance (%) 0.025 2 . 1 0 1 1 5 0.012 4 3-4 0 3. -4 1 0 = no fungal infection, gradually up to 5 = total infection Table IV Active substance Infection of leaves after spraying the liquid from example no. Containing 0.025% of the active substance IV 0 VIII 0 XVII 1 XX 0 XXI 1-2 XXIV 1 Compound C (comparative measure) 2-3 Control (untreated) 5 0 = no fungus contamination, gradually to 5 = total infection Table V Active substance Infection of leaves after spraying the liquid from example No. containing 0.025 % of active substance X 0 XXI 0 Compound A (reference agent) 2 Control (untreated) 5 0 = no fungal infection, gradually up to 5 = total infection 123,432 CH, X- X- CH3 CH_R1 O c-r2 0 FORMULA 1 / CH, OR CH, I 3/1 J / CH-CH 5 and "R 0 FORMULA Ia CH3? H3, CH-R1 X ^ (() -n ', R X-CH ^ Jl \ 0 Ha l FORMULA 1 b CH ^ NH- FORMULA 3 CH: 9H3 3 / CH- COOCHo O C0-CH3: H3 XH-CCOCH, (C \ XO-CH2-Br FORMULA 4 FORMULA 5 CH3 CH3 CH-COOCH3 M xco-ch2- nTj FORMULA 6 CH CH: I * 3 CH-COOCH3 CH- s' V CH <FORMULA 7123432 CH- H: Br N XH-COOCH3 \; o- ^ V FORMULA 8 CHo IO CH3 CH_cA-pH2 tTCH2 OK MODEL 9 CH- CH- '3 CH-CHO (^ CO-CH2Br FORMULA 10 -s FORMULA CH2- N j N 11 FORMULA 12 ^ FORMULA 13 -O) N FORMULA U ^ ° FORMULA 15 CH. FORMULA 16 -SvN CH3 FORMULA 17123432 NH- OorCH \ I 3 Br-CH-COOCH- I 3 Mu CH-COOCH-, NH and J HBr to ¦CH3 SCHEME 1 NH2 H- QQf * CH3-CD-COOC2H5 ^ QO CH3 n = c-cooc2h5 CH-, SCHEME 2 CH3 NH- H ^ POT? CHjCO-CH (OCH ^ 2 - ^ - Q ^ N = C-CHfOCH ^ 2 CH3 SCHEME 3 CH3 N = C- CH: COOC ^ Hg CH3 NH -CH-COOCjHj -OÓrCH3 SCHEME 4 Printing workshop of the Polish People's Republic. Mintage 100 pcs. Price PLN 100 PL
PL1980228213A 1979-12-04 1980-12-02 Fungicide PL123432B2 (en)

Applications Claiming Priority (1)

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DE19792948704 DE2948704A1 (en) 1979-12-04 1979-12-04 N-SUBSTITUTED 2-METHYLNAPHTHYLAMID, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM

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PL228213A2 PL228213A2 (en) 1981-08-07
PL123432B2 PL123432B2 (en) 1982-10-30
PL123432B1 true PL123432B1 (en) 1982-10-31

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US (1) US4430336A (en)
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JP (1) JPS5692851A (en)
AT (1) ATE2510T1 (en)
AU (1) AU6503180A (en)
BR (1) BR8007690A (en)
CA (1) CA1153002A (en)
CS (1) CS215143B2 (en)
DE (2) DE2948704A1 (en)
DK (1) DK515180A (en)
HU (1) HU185622B (en)
IE (1) IE50726B1 (en)
IL (1) IL61515A (en)
MA (1) MA19006A1 (en)
NZ (1) NZ195740A (en)
PL (1) PL123432B2 (en)
SU (1) SU1060095A3 (en)
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MA19215A1 (en) * 1980-07-25 1982-04-01 Ciba Geigy Ag NOVEL ARYLAMINE DERIVATIVES, PROCESS FOR THEIR MANUFACTURE AND USE AS MICROBICIDES.
DE3126083A1 (en) * 1981-07-02 1983-01-20 Basf Ag, 6700 Ludwigshafen N-SUBSTITUTED 2-METHYLNAPHTHYLAMID, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM
DE3126082A1 (en) * 1981-07-02 1983-01-20 Basf Ag, 6700 Ludwigshafen GLYCOLETHERIC ACID APHTHYLAMIDS, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM
DE3135239A1 (en) * 1981-09-05 1983-03-17 Basf Ag, 6700 Ludwigshafen N-SUBSTITUTED PETROLEUM ACID AMIDES, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM
DE3135238A1 (en) * 1981-09-05 1983-03-17 Basf Ag, 6700 Ludwigshafen N-ALKINYL-NAPHTHYLAMIDES, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM
DE3135670A1 (en) * 1981-09-09 1983-03-24 Basf Ag, 6700 Ludwigshafen OXALAMID, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THE SAME
DE3144140A1 (en) * 1981-11-06 1983-05-19 Basf Ag, 6700 Ludwigshafen 2-ISOXAZOLINE CARBONIC ACID AMIDES, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM
DE3144951A1 (en) * 1981-11-12 1983-05-19 Basf Ag, 6700 Ludwigshafen ISOXAZOLE-CARBONIC ACID AMIDES, THEIR PRODUCTION AND THEIR USE AS FUNGICIDES
JPH0613445B2 (en) * 1985-09-10 1994-02-23 保土谷化学工業株式会社 Paddy seed dressing agent
WO2000060940A1 (en) * 1999-04-12 2000-10-19 Dow Agrosciences Llc Aqueous dispersions of agricultural chemicals
RU2646058C1 (en) * 2017-07-06 2018-03-01 Ксения Леонидовна Алексеева Method of greenhouses protection from tomato powdery mildew

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US2412510A (en) 1944-06-02 1946-12-10 American Chem Paint Co Methods and compositions for killing weeds
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US3272844A (en) 1965-06-03 1966-09-13 Lilly Co Eli Novel acetylenic amides
DE1670172C3 (en) 1966-12-09 1974-04-04 C.H. Boehringer Sohn, 6507 Ingelheim 2- (3,4-dichloroanilinocarbonyl) isoxazolidine
US3549704A (en) * 1967-05-19 1970-12-22 Philips Corp Salicylamides
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US4098895A (en) 1975-09-30 1978-07-04 Ciba-Geigy Corporation Triazolylacetanilide compounds and microbicidal compositions
DE2845454A1 (en) 1977-11-01 1979-05-10 Chevron Res 3- (N-ACYL-N-ARYLAMINO) - GAMMA -BUTYROLACTONE AND - GAMMA -BUTYROTHIOLACTONE AND FUNGICIDE AGENTS
US4221584A (en) 1979-02-09 1980-09-09 Chevron Research Company Herbicidal and plant-growth-regulating N-(heterocyclyl)-methylacetanilides
MA18800A1 (en) * 1979-04-10 1980-12-31 Ciba Geigy Ag ACYLATED NAPHTYLAMINES, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS PHYTOFUNGICIDES

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