IE781028L - Furanecarboxylic acid anilides - Google Patents

Furanecarboxylic acid anilides

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Publication number
IE781028L
IE781028L IE781028A IE102878A IE781028L IE 781028 L IE781028 L IE 781028L IE 781028 A IE781028 A IE 781028A IE 102878 A IE102878 A IE 102878A IE 781028 L IE781028 L IE 781028L
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IE
Ireland
Prior art keywords
furan
oxoperhydro
furyl
carboxylic acid
anilide
Prior art date
Application number
IE781028A
Other versions
IE46922B1 (en
Original Assignee
Schering Ag
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Publication date
Priority claimed from DE19772724785 external-priority patent/DE2724785A1/en
Application filed by Schering Ag filed Critical Schering Ag
Publication of IE781028L publication Critical patent/IE781028L/en
Publication of IE46922B1 publication Critical patent/IE46922B1/en

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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
    • 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
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—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
    • A01N43/14—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 six-membered rings
    • A01N43/16—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 six-membered rings with oxygen as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

New furancarboxanilides have the following formula <IMAGE> in which R1 denotes hydrogen or C1-C4-alkyl, R2 denotes an aromatic hydrocarbon radical or an aromatic hydrocarbon radical which is substituted one or more times by identical or different substituents comprising C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, halogen, trifluoromethyl, nitro, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl and/or cyano, and n denotes the numbers 1 or 2. Fungicides which can be used for combating phytopathogenic fungi contain a compound of the formula I as at least one active component. The new compounds of the formula I are prepared by reacting appropriately substituted perhydrofuran-2-one compounds with a carboxylic acid chloride. [CH637393A5]

Description

4 6 9 2 2 -2- The present invention 1s concerned with new fungicidally active furancarboxylic acid anilides, with the use of these compounds for controlling phytopathogenic fungi and also with a process for the manufacture of the new 5 active compounds.
Agents that act against phytopathogenic fungi have already been known. Agents of this type known in practice are, for example, 5 - ethoxy - 3 - trichloromethyl - 1,2,4 -thiadiazole (United States Patent Specifications Nos. 10 3,260,725 and 3,260,588) and tetramethylthiuram disulphide (German Patent Specification No. 642,532). However, these agents do not always have a satisfactory action against leaf and soil fungi.
The problem upon which the present invention is based 15 has been to provide an agent having a superior action against leaf and soil fungi. This problem is now solved 1n accordance with the present invention by the compounds of the general formula I, as defined below.
The present invention provides compounds of the general 20 formula I I 4 6 9 2 2 -3- R 2 H (CH2)n-CH-N-CO 0 (I) R in which R^ represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, Rg represents an unsubstituted aromatic hydrocarbon group 5 or an aromatic hydrocarbon group substituted by one or more substituents selected from alkyl groups containing 1 to 4 carbon atoms, alkoxy groups containing 1 to 4 carbon atoms, alkylthio groups containing 1 to 4 carbon atoms, halogen atoms, trif1uoromethy1 groups, nitro groups, alkoxycarbonyl ]0 groups containing 1 to 4 carbon atoms in the alkoxy parts, alky1carbonyl groups containing 1 to 4 carbon atoms in the alkyl parts and cyano groups, and n represents 1 or 2.
When the substituted aromatic hydrocarbon group represented 15 by R^ contains two or more substituents these substituents may be the same or different.
It is to be understood herein that when the unsubstituted or substituted aromati-c hydrocarbon group represented by ,46922 -4 f*2 contains more than one aromatic ring, these rings may be fused together in the ortho-positions or may be isolated as in, for example, biphenyl.
The action.of the compounds of the present invention against 5 leaf and soil fungi is surprisingly superior to that of known agents having the same direction of action and these compounds are also distinguished by a good plant tolerance and a sufficient duration of action. In addition, since they do not act phytotoxically when applied in the quantities suitable 10 in practice, they may accordingly be used advantageously in agriculture and horticulture for the control of leaf and soil fungi.
The compounds of the present invention have outstanding fungicidal properties against harmful fungi.
In contrast to known fungicidal agents having only a preventive 15 action, such as, for example, N-trichloromethyl thiophthalimide (United States Patent Specification No. 2,553,770) and manganese ethylene; bisdithiocarbamate (United States Patent Specification No. 2,504,404) the compounds of the present invention surprisingly also have the additional 20 advantage of a curative and systemic action which, therefore, makes i:t possible also to control pathogenic agents which have already penetrated into the plants.
The present invention accordingly also provides a fungicidal 46922 -5- preparation which, comprises a compound of the general formula I, in admixture or conjunction with a suitable carrier. The preparation may of course contain one or more compounds of the general formula I.
The present invention further provides a method of protecting a living plant against phytopathogenic fungi, wherein the living plant is treated with a compound of the general formula I.
! The present invention further provides a method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with a compound of the general formula I.
The present invention further provides a method of dressing seeds, wherein the seeds are treated with a compound of the general formula I.
The present invention further provides a pack which comprises a compound of the general formula I together with instructions for its use for controlling phytopathogenic fungi.
The compounds of the present invention that are especially distinguished by a superior fungicidal action are those of the general formula I in which R1 represents a hydrogen atom or a methyl or ethyl group and R2 represents a phenyl,' methyl phenyl, dimethyl phenyl, ethyl phenyl , isopropylphenyl, 4 69 2 2 . . ^ methoxyphenyl, ethoxyphenyl, methyl thi ophenyl, f luorophenyl chlorophenyl, bromophenyl, dichlorophenyl, trif1uorophenyl, nitrophenyl, cyanophenyl, methoxycarbonylphenyl, acetylphenyl or blphenylyl group.
The new active compounds may be applied singly or, alternatively, mixtures of at least two constitutionally different compounds of the general formula I may be applied. If desired, other fungicides, nematocides, herbicides or other types of pest-controlling agents may be added depending on the purpose. The active substances are advantageously applied in the form of fungicidal preparations, for example powders, strewable preparations, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid vehicles or diluents and, if desired, of wetting, adhesive, emulsifying and/or dispersing agents.
Suitable liquid carriers are, for example, water, mineral oils or other organic solvents, for example xylene, chlorobenzene, cyclohexanol, cyclohexanone , dioxan, acetonitrile, ethyl acetate, dimethylformamide, isophorone and dimethyl sulphoxide.
Suitable solid carriers are, for example, lime, kaolin, chalk, talcum, attaclay and other clays as well as natural or synthetic silicic acid.
As surface-active agents there may be mentioned, for example, -7- 469 22 salts of lignin sulphonic acid, salts of alkylated benzenesulphonic acids, sulphonated acid amides and salts thereof, polyethoxy1ated amines and alcohols.
When the active substances are to be used for dressing 5 seeds, they may also be admixed with dyestuffs in order to give the dressed seeds a clearly visible colour.
The proportion of active substance(s) in the fungicidal preparations may vary within wide limits, the exact concentration of the active substances used for the 10 preparations depending primarily on the quantity in which the preprations inter alia are to be used for treating soil or seeds or for treating parts of plants above the soil. The preparations may contain, for example, approximately 1 to 80% by weight, preferably between 20 and 50% by weight, ■}5 of active compound(s), approximately 99 to 20% by weight of liquid or solid carrier and also, if desired, up to 20% by weight of surface-active agent(s).
The new compounds of the general formula (I) may be produced by the process of the present invention, as defined below. 20 The present invention further provides a process for the manufacture of a compound of the general formula I, wherein a compoun-d of the general formula II 46922 v. ■ •• , " iZ" ' v (CH9) CH-NH-R, (II). in which R^, R2 and n have the meanings given above, is reacted in the presence of an acid-binding agent and, if desired, a solvent with a furancarboxylic acid chloride of the formula III CI-CO (IH)» The compound of the general formula II and the compound of the formula III are preferably used in equimolar proportions.
As acid-binding agents there may be used, for example, organic bases, for example pyridine, triethyl amine or N,N-dimethyl-aniline, or inorganic bases, for example hydroxides, oxides 10 and carbonates of alkali metals and alkaline earth metals, for example sodium, potassium or calcium. The compound of the general formula II may itself act as the acid-binding agent.
As a solvent that may optionally be used, there may be 46922 -9- mentioned, for example, ether, tetrahydrofuran, benzene or ethyl acetate. Liquid acid-binding agents, for example pyridine, may servie simultaneously as solvents.
The reaction is advantageously carried out at a temperature within the range of from -10°C to 120°C.
The products of the process of the present invention may be isolated in a manner known per se.
Some specific compounds of the present invention are listed in the following Table.
Name Physical constant Furan-2-carboxylic acid [N-(2- oxoperhydro-3-furyl)-2,6-dimethylanilidej M.p.: 135-138°C M.p.: 98-100°C M.p.: 140-141°C M.p.: 124-125°C M.p.: 127-1 29°C M.p.: 139-140°C Furan-2-carboxyl i c acid J^2-ch1oro-n-(2-oxoperhydro-3-furyl)-ani 1 ide] Furan-2-carboxylic acid [n-(2-oxo-perhydro-3-furyl) - a n i 1 i dej Furan-2-carboxyl i c acid J^2,6-diethyl-n-(2-oxoperhydro-3-furyl)-ani1i dej Furan-2-carboxyl i c acid [j>-ethyl-6-methyl-n-(2-oxoperhydro-3-fury1)-ani1i de] Furan-2-carboxylic acid [V-methoxy-n-(2-oxoperhydro-3-furyl)-ani1i del • VVMM -1(3- Name Physical constant 10 15 20 25 Furan-2-carboxyl1c acid £2,6-dimethyl N-(5-methyl-2-oxoperhydro-3-furyl)-anil ide"] Furan-2-carboxylic acid £3,4-dichloro-N-(2-oxoperhydro-3-furyl)-ani 1 i dej Furan-2-carboxylic acid ^2-methyl-N-(2-oxoperhydro-3-furyl)-anilide] Furan-2-carboxyl1c acid £2,4-dimethyl■ N-(2-oxoperhydro-3-furyl)-ani 1 i dej Furan-2-carboxylic acid ^3,4-dlmethyl■ N-(2-oxoperhydro-3-furyl)-ani1i de Furan-2-carboxylic acid [2,3-dimethy1• N(2-oxoperhydro-3-furyl)-anili dej Furan-2-carboxyl 1 c acid |j3,5-dimethyl -N-(2-oxoperhydro-3-furyl)-ani 1 i de] Furan-2-carboxylic acid £2,4,6-t ri methyl - N- (2-oxoperhydro-3-.furyl) anilldej Furan-2-carboxyl1c acid ^3-methyl-N-(2-oxoperhydro-3-f uryl) - ani 1 i de] Furan-2-carboxylic aci d £4-methyl - N-(2-oxoperhydro-3-furyl )-anH1de] Furan-2-carboxyl ic acid {^3-chloro-N ' - (2-oxoperhydro-3-furyl)-ani1idej Furan-2-carboxy1ic acid pl-chloro-N - (2-oxoperhydro-3-furyl)-ani1i de J Furan-2-carboxylic acid ^2-ethyl-N - (2-oxoperhydro-3-furyl)-ani1idej M.p.: 190-191 C M.p.: 139-141 C M.p.: 132 C M.p.: 123-124 C M.p,: 122C M.p.: 129-130 C M.p.: 161-162 C M.p.: 142-143 C M.p.: 121 C M.p.: 118-119 C M.p.: 134-135 C M.p.: 157-158 C M.p.: 122-123 C 4 6 9 2 2 10 -11 Name Physical constant Furan-2-carboxylic acid£N-(2-oxoperhydro -3-furyl)-3-trifluoro- methyl-ani1i de J M.p.: 130-131°C Furan-2-carboxyl ic acid 1.4-isopropyl -N-(2-oxoperhydro-3-furyl)-ani1idej M.p.: 95-96°C Furan-2-carboxylic acid ^3-bromo-N -(2-oxoperhydro-3-furyl)-ani1idej M.p.: 150-153°C Furan-2-carboxylic acid C4-methoxy- N-(2-oxoperhydro-3-furyl)-ani1idej M.p.: 149-151°C Furan-2-carboxylic acid ^4-ethoxy- N-(2-oxoperhydro-3-furyl)-ani1ide] M.p.: 87-88°C Furan-2-carboxylic acid [4-ethyl- N-(2-oxoperhydro-3-furyl)-ani1i d^] M.p.: 120-121°C 15 Furan-2-carboxylic acid [4-bromo -N-(2-oxoperhydro-3-furyl)-ani 1 i dej M.p.: 1 37-140°C Furan-2-carboxylic acid ^3-fluoro -N-(2-oxoperhydro-3-furyl)-ani1ide] M.p.: 142-144°C Furan-2-carboxylic acid ^4-fluoro 20 -N-(2-oxoperhydro-3-furyl)-ani1i dej M.p.: 165-166°C Furan-2-carboxylic acid Ql-methoxy -2-methyl-N-(2-oxoperhydro-3- furyl)-ani1idej M.p.: 133-135°C Furan-2-carboxylic acid [2,5-25 dimethyl-N-(2-oxoperhydro-3-furyl) -ani1i dej M.p.: 120-121°C 46922 -12- 10 15 20 25 Name Physical constant Furan-2-carboxyl1c acid [2-ethoxy- N-(2-oxoperhydro-3-fury1)-anilide| M.p.: 150°C Furan-2-carboxylic acid [2,6-di isopropyl-N-(2-oxoperhydro-3- furyl)-ani1ideJ M.p.: 149-150°C Furan-2-carboxylic acid £3,5-dichloro -N-(2-oxoperhydro-3-furyl)-ani1ide] M.p.: 143-145°C Furan-2-carboxy1ic acid ^3-chloro -2-methyl-N-(2-oxoperhydro-3-furyl) -anllide] M.p.: 151 °C Furan-2-carboxyl i c acid J]5-chloro-2 -methyl-N-(2-oxoperhydro-3-furyl) -anllide] M.p.: 138-139°C Furan-2-carboxylic acid £2-methoxy-carbonyl-N-(2-oxoperhydro-3- furyl)-ani1idej M.p.: 110-112°C Furan-2-carboxyl 1 c acid [^3-methoxy- N-(2-oxoperhydro-3-furyl)-ani 1 ide] M.p.: 145-148°C Furan-2-carboxylic acid ^3-nitro -N-(2-oxoperhydro-3-furyl)-ani1ide} M.p.: 137-138°C Furan-2-carboxylic acid £3-chloro -N-(5-methyl-2-oxoperhydro-3-fury1) -anllide] M.p.: 105-108°C Furan-2-carboxy1ic acid ^3-methyl-thi o-N-(2-oxoperhydro-3-furyl)- anllide] M.p.: 154-155°C 409 22 -13- Name Physical constant Furan-2-carboxyl ic acid fs-chloro-2-methoxy-N-(2-oxoperhydro-3-furyl) -ani1 i de ] 5 Furan-2-carboxylic acid ^3-fluoro-N -(5-methyl-2-oxoperhydro-3-furyl) -ani1i de ] Furan-2-carboxyl i c acid £*4-phenyl-N - (2-oxoperhydro-3-furyl)-ani1i de 3 10 Furan-2-carboxylic acid ^3-acetyl -N-(2-oxoperhydro-3-furyl)-ani 1 i de] Furan-2-carboxylic acid ^2-chloro-6-methyl-N-(2-oxoperhydro-3-furyl) -ani 1 i de"] Furan-2-carboxylic acid ^2-bromo-N-(2-oxoperhydro-3-furyl)-ani 1 i de] Furan-2-carboxylic acid [2,3-dichloro -N-(2-oxoperhydro-3-fury1)-ani1i dej Furan-2-carboxylic acid [3-chloro 20 -2-methoxy-N-(2-oxoperhydro-3-furyl) -anilide] Furan-2-carboxylic acid {[3-ethy 1 -N - (2-oxo perhydro-3-fury 1) - ani 1 i de"] Furan-2-carboxylic acid [3-cyano-N-25 (2-oxoperhydro-3-furyl)-anilide] M.p, M.p.
M.p.
M.p, M.p. 171-173 C M.p.: 93-94°C M.p.: 186-187 C M.p.: \66-167°C 145-148°C 11 8°C 1 26°C M.p.: 115/116-117°C 128-129 C M.p.: 131/132-134°C The compounds of the present invention are generally almost 40922 -14- colourless, odourless, crystalline substances that are practically insoluble in water and benzine but, on the other hand, very readily soluble in polar organic solvents, for example acetone, dimethylformamide and 5 dimethyl sulphoxide.
The starting compounds for the manufacture of the compounds of the present invention are known per ee or may be produced according to processes known per se.
. * ' The following Examples illustrate the invention. Examples 10 1 to 3 illustrate the manufacture of the compounds of the present invention and Examples 4 to 13 illustrate the possibilities of application of the compounds of the present invention.
Example 1 15 Furan-2-carboxylic acid £n-(2-oxoperhydro-3-furyl)-2,6-dlmethylani1ideJ 206.2 g (1.58 mole) of furan-2-carboxy1ic acid chloride were added dropwise, at room temperature and while stirring, to a solution of 300 g (1.46 mole) of 3 - (2,6 - dimethylani1ino) 20 - perhydrofuran - 2 - one in 600 ml of dry pyridine. After the addition was complete a pyridine complex precipitated out with a simultaneous increase in temperature. Heating was effected for 3 hours at 50°C and the whole was then concentrated in vacuo to half its volume. The mixture was 25 then poured, while stirring, into 2.5 1 of ice-cold 5% 4 6922 -15- hydrochloric acid and after 30 minutes filtered with suction. Washing with a large amount of water and drying in vacuo at 70°C were then carried out.
Yield: 387 g-89% of the theoretical yield. 5 M.p.: 135-138°C Example 2 Furan-2-carboxylic acid |^2-chloro-N-(2-oxoperhydro-3-furyl)-ani1idej 13.05 g (0.1 mole) of furan-2-carboxylic acid chloride 1 were added at room temperature to 21.16 g (0.1 mole) of 3 - (2 - chloranilino) - perhydrofuran - 2 - one. The reaction mixture was heated slowly to 120°C and maintained at this temperature for 1.5 hours until the evolution of hydrogen chloride had been completed. After 1C cooling, 100 ml of ethyl acetate were added and the I 0 mixture was washed until neutral with a saturated sodium bicarbonate solution. The ethyl acetate phase was dried with magnesium sulphate, filtered and concentrated -in vacuo. The resulting oil was crystallized with a little ether 20 and filtered off with suction, and the resulting crystals were washed with diisopropyl ether.
Yield: 21.4 g = 70% of the theoretical yield.
M.p.: 98-100°C 4 6822 -16- Example 3 Furan-2-carboxyl i c acid [Jl-(2-o>toperhydro-3-f uryl) - an i 1 i A solution of 14.16 g (0.08 mole) of 3-ani11 noperhydrofuran -2-one in 150 ml of ethyl acetate and a solution of 9.54 5 g (0.09 mole) of sodium carbonate in 15 ml of water were mixed by stirring. 11.70 g (0.09 mole) of furan-2-carboxylic acid chloride were then added dropwise while cooling with ice. The mixture was then stirred for an hour, if necessary neutralized with a little soda solution and extracted 10 by shaking with ethyl acetate. After drying over magnesium sulphate the ethyl- acetate solution was concentrated to dryness in vacuo and the solid residue was treated with a little ether/ethanol. The whole was filtered with suction, washed with ether and recrystal1ized from ethanol.
^ Yield: 10.6 g=49% of the theoretical yield.
M.p.: 140-141°C Each of the other compounds of the present invention listed in the Table above may be produced in a manner analogous to that described in any one of Examples 1 to 3. 20 Example 4 Limiting concentration test in the control of Pythium ultimum In a series of tests 20% pulverulent active substance preparations were mixed uniformly with soil which was severely infected with Pythium ultimum. The treated soil was placed 25 in clay dishes each having a capacity of 0.5 litre and, without 46922 -1 7- a waiting period, 20 marrowfat pea seeds of the Kelvedon Wonder variety were sown in each dish. After a cultivation period of 3 weeks at 20 to 24°C the number of sound peas was determined and a root assessment (1-4 as defined below) was carried out.
The active substances and also the results, used and their application quantities, are given in the following Table.
Compound according to the invention Active substance concentration in mg/1 soil Number of sound peas Root assessment (1-4) Furan-2-carboxylic acid £n-(2-oxoperhydro-3-furyl)-ani1idej 10 mg 20 mg 40 mg 10 14 15 2 3 4 Furan-2-carboxylic acid £n-(2-oxoperhydro-3-furyl)-2,6-dimethylanilideJ 10 mg 20 mg 40 mg 16 16 19 4 4 4 Furan-2-carboxylic acid £2,6-dimethyl- 10 mg 7 2 N-(5-methyl-2-oxoperhydro-3-furyl)- 20 mg 15 3 anilidej 40 mg 18 4 Furan-2-carboxylic acid Q-methyl-N- 10 mg 4 1 (2-oxoperhydro-3-furyl)-anilidej 20 mg 9 2 40 mg 17 3 Furan-2-carboxylic acid L,3-chloro-N- 10 mg 14 3 (2-oxoperhydro-3-furyl)-anilideJ 20 mg 19 4 40 mg 17 4 Compound according to the invention Active substance concentration in mg/1 soil Number of sound peas Root Assessment (1-4) Furan-2-carboxyl i c acid Q-bromo-N- 10 mg 10 2 (2-oxoperhydro-3-furyl)-ani1ide ] 20 mg 15 4 40 mg 14 4 Furan-2-carboxylic acid [3-fluoro-N- 10 mg 10 3 (2-oxoperhydro-3-furyl)-anilide} 20 mg 16 4 40 mg 19 4 Agent for comparison 5-Ethoxy-3-trichloromethyl-1,2,4- 10 mg 2 1 thi adi azole 20 mg 5 1 40 mg 12 3 Control I (3 repetitions) a) 1 1 Infected soil b) c) 0 0 - Compound according to the invention Active substance concentration in mg/1 soil Control II (3 repetitions) Steamed soil a) b) c) Number of sound peas 19 18 18 Root q assessment « (1-4) N 10 4 4 4 -21- 4 6 9 2 2 Example 5 Dressing of sugarbeet seeds In a series of tests graded sugarbeet seeds of the Dieckmann-Suprapoly variety were dressed with 20% pulverulent active 5 substance preparations. Clay dishes each of 2 litres capacity (20x20x5 cm) were filled with normal compost soil (damping-off) and 100 of the sugarbeet seeds were sown in each dish. After a cultivation period of 18 days at 19-21°C in a greenhouse the number of sound seedlings was determined. 10 The active substances used and their application quantities, and also the results, are given in the following Table Compound according to the invention Furan-2-carboxylic acid £n-(2-oxoperhydro-3-furyl)-2,6-dimethylanilide] Furan-2-carboxylic acid ^3-chloro-N-(2-oxoperhydro-3-furyl)-ani1i de J Furan-2-carboxyl i c acid (^3-f 1 uoro-N-(2-oxoperhydro-3-furyl)-ani1i de} Active substance in g/kg seed Number of sound seedlings from 9 CD M BS 100 seeds 0.4 g 0.8 g 1.6 g 84 90 91 0.4 g 0.8 g 1.6 g 73 71 91 I ro ro i 0.4 g 0.8 g 1.6 g 75 79 75 10 Furan-2-carboxylic acid £2,3-dimethyl 0.4 g 74 -N-(2-oxoperhydro-3-furyl)-ani1ide} 0.8 g 82 1.6 g 85 Furan-2-carboxylic acid [3-methyl- 0.4 g 72 N-(2-oxoperhydro-3-furyl)-anilideJ 0.8 g 78 1.6 g 79 Compound according to the invention Active substance in g/kg seed Number of sound seedlings from 100 seeds Furan-2-carboxylic acid ^2,6-dimethyl 0.4 g 57 -N-(5-methy1 -2-oxoperhydro-3-furyl)- 0.8 g 70 ani 1 i de] 1.6 g 92 Furan-2-carboxylic acid [3-bromo-N- 0.4 g 56 (2-oxoperhydro-3-f uryl) - ani 1 i de.] 0.8 g 55 1.6 g 75 Agents for comparison 5-Ethoxy-3-trichloromethyl-l,2,4- 0.4 g 26 thi adi azole 0.8 g 44 1.6 g 53 Tetramethylthiuram disulphide 4.8 g 21 9.6 g 50 Compound according to the invention Active substance Number of sound ■ „ .. seedlings from in g/kg seed ,Q0 see»s Control I (3 repetitions) a) 5 Infected soil b) 7 c) 6 Control II (3 repetitions) a) 83 Steamed soil b) 86 c) 81 4 6 9 2 2 -25-Example 6 Control of Pythium eplendens in the pot cultivation of Poinsettia pulohevvima In a series of tests young poinsettia plants of the Annette 5 Hegg Diva Variety, which had taken root were potted in clay pots each of 11 cm in diameter. The pot substrate (peat culture substrate+sandy compost soil 1:1) was severely infected with Pythium splendens. After potting, 100 ml of the preparation under test and having the concentration 10 indicated in the Table below were poured once over the plants. There followed a cultivation period of 10 weeks at 20 to 21°C in a greenhouse. At the end of the cultivation period the height of each of 10 plants was measured, the fresh weight of the leaves and bracts was determined and a root assessment 15 (1-4 as defined below) was carried out.
The active substances used and their application quantities, and also the results are given in the following Table.
Compound according to the invention Active substance concentrati on Hei ght of the pi ants Fresh weight of the leaves Fresh weight Root * of bracts assessments (1-4) ® 10 Furan-2-carboxylic acid £n 0.02% -(2-oxoperhydro-3-furyl)- 0.04% 2 ,6-dimethylani1idej 0.08% 40 cm 39 cm 42 cm 13 g 12 g 13 g 16 g 13 g 11 g 4 4 4 Furah-2-carboxylic acid £n -(2-oxoperhydro-3-fury!)-anil ide^J Control I Infected soil 0.02% 0.04% 0.08% 38 cm 37 cm 35 cm 12 cm 13 g 12 g 13 g 4 g 13 g- 14 g 15 g 4 g 3 3 3 Control II Steamed soil 43 cm 17 g 15 g Root assessment: 4=no attack 3= slight attack 2= average attack 1= severe attack 469 2a -27-Example 7 Control of bulb soft rot and bulb root rot in tul i p cultivation In a series of tests prepared tulip bulbs (5°C tulips) of the Gander variety were peeled and 12 bulbs in each case 5 were planted in wooden boxes each measuring 27x27x12 cm.
The plant substrate (sandy compost soil) was severely infected with Pythium ultimum and Pythium sylvatioum. The preparation under test, as a 10% pulverulent preparation, was worked uniformly into the compost before planting. There followed ■jq a cultivation period of 47 days at a soil temperature rising slowly from 12 to 17°C. The mature flowers were weighted, the plant losses as a result of bulb rot were determined, and a root assessment (1-4) as defined below) was carried out. 15 The active substance used and its application quantities, and also the results, are given in the following Table Compound according to the invention Active substance concentration in mg/1 soil Average weight of the mature f 1 owers Plant loss through bulb rot Root assessment (1-4) Fur'an-2-carboxy li c acid^N- 10 mg 45 g 0% 4 (2-oxoperhydro-3-furyl)- 20 mg 45 g 0% 4 2,6-dimethyl ani 1 i dej 40 mg 47 g 0% 4 Control I - Infected soil 22 g 92% 1 Control II Steamed soil 33 g 75% 1 Root assessment: 4= no attack 3= slight attack 2= average attack 1= severe attack 4 6 9 2 2 -29- 10 Example 8 Control of Phytophthora parasitica var. nicotianae in the pot cultivation Of Sinningia epeciosa (Gloxinia) In a series of tests young Sinningia plants of the Gierth's Blaue variety were potted in clay pots each of 11 cm in diameter. The pot substrate was a 1:1 mixture of peat culture substrate and sandy compost soil. After potting, 100 ml of the preparation under test and having the concentration indicated in the Table below were poured once over the plants. 3 days afterwards the pots were inoculated uniformly with mycelium flocci of a 3-week-old Phytophthora culture. There followed a cultivation period of 7 weeks at 22 to 24°C in a greenhouse.
The active substance used and its application quantities, and also the results, are given in the following Table 15 Compound according to the invention Active Plant losses substance after 7 weeks concentrati on, Average fresh weight of the plants after 7 weeks 20 Furan-2-carboxylic 0.01% acid[N-(2-oxoperhydro 0.02% -3-furyl)-2 ,6-dimethyl 0.04% -ani 1 i de^] 0% 0% 217 g 259 g 223 g Control I Inoculated 80% 140 g Control II Not inoculated 0% 239 g VVfjH.' --•♦J*-' 46922 10 -30- 15 Example 9 Control of Pythium ultimum in the propagation of Pelargonium cuttings In a series ofitests clay pots each of 6 cm in diameter were filled with a propagation substrate which was severely infected with Pythium ultimum. The substrate was a mixture of 3 parts of peat culture substrate and 2 parts of sand. 30 ml of the active substance concentration indicated in the Table below was poured on to the soil surface in each pot. Afterwards, shoots, which had not taken root, of Pelargonium peltatum of the Luisenhof variety were planted in 24 pots per test series. After a cultivation period of 25 days at 22 to 25°C in a propagation bed the plant losses were ascertained and the average fresh weight of the cuttings which had taken root was determined.
The active substances used and their application quantities, and also the results, are given in the following Table.
Compound according to the invention Active Plant substance losses concentrati on Average fresh weight of the plants 20 Furan-2-carboxyli c acid ^3-chloro-N-(2-oxoperhydro-3-furyl) -ani1i dej 0.005% 0.01% 0% 0% 7.3 g 7.1 g 25 Furan-2-carboxylic acid 0.005% [N-(2-oxoperhydro-3- 0.01% furyl)-2,6-di methyl -ani1i dej 0% 0% 6.2 g 6.8 g -31- 4U&22 Compound according to the invention Acti ve substance concentrati on Plant losses Average fresh weight of the plants Control I Infected soil 83% 2.6 g Control II Steamed soil 0% 6.8 g Example 10 Effect of prophylactic leaf treatment against Plasmopara viticola on vines in a greenhouse In a series of tests young vines having approximately 5 to 8 leaves were sprayed until dripping wet with the concentration of active substance indicated in the Table below and, after the spray coating had dried on, an aqueous suspension of sporangia of the fungus indicated in the heading above (approxmimately 20,000 per ml) was sprayed on the undersides of the leaves and plants were then immediately incubated in a greenhouse at 22 to 24°C in an atmosphere as saturated with steam as possible. From the second day on the air humidity was reduced for 3 to 4 days to the normal level (30 to 70% saturation) and then maintained for a further day at steam saturation. The percentage proportion of the surface attacked by fungi of each leaf was then noted and the average per treatment was calculated as follows to determine the fungicidal effect: '■mm* • •'"* • " ni "'I?'" »' I •• .• 46922 -32- lOOxattack in treated plants 100 : : =% effect attack in untreated plants % Effect against Plasmopara viticola in vines +) 5 Compound according Concentration (%active to the invention substance) 0.001 Furan-2-carboxylic acid £n- 100 (2-oxoperhydro-3-furyl)-2,6-dimethylani1idej 10 Furan-2-carboxyl ic acid 100 [2,6-dimethyl-N-(5-methy1-2-oxoperhydro-3-furyl)-ani1i de ] Furan-2-carboxylic acid [ 3- 98 15 chl oro-N-(2-oxoperhydro-3- furyl)-ani1ide ] Agent for comparison N-Trichloromethyl thio 80 phthalimide 20 +) Effect was calculated on 100% attack in the untreated control I I Example 11 Effect of prophylactic leaf treatment against Phytophthora infeatans in tomato plants or potato plants in a greenhouse ; In a series of tests young tomato plants having at least two 25 develo-ped foliage leaves and potato plants (for example from 46922 -33- eye cuttings) at least 10 cm tall were sprayed until dripping wet with the concentration of active substance indicated in the Table below and, after the spray coating had dried on, they were sprayed with an aqueous suspension which contained per millilitre 50,000 to 80,000 sporangia of the fungus indicated in the heading above and which had been incubated for approximately 2 hours in a refrigerator at 11°C. The plants were incubated at a high level of air humidity and approximately 15 to 18°C in a greenhouse and after approximately 5 days the percentage proportion of the leaf surface that had been attached was assessed. The fungicidal effect was calculated as follows: lOOxattack in treated plants 100 =% effect attack in untreated plants % Effect against Phytophthora infestans in potatoes +) Compound according to the invention Concentrati on (% active substance) 0.005 0.001 Furan-2-carboxylic acid £N-(2-oxoper- 70 hydro-3-furyl)-ani 1 i del Furan-2-carboxylic acid £N-(2-oxoper- 100 hydro-3-furyl)-2,6-dimethyl - ani 1 ide] Furan-2-carboxylic acid £ 2 ,6-dimethyl-N 95 -(5-methy1 -2-oxoperhydro-3-furyl)-ani1i del 95 90 Agent for comparison Manganese ethylene bisdithiocarbamate 50 I % Effect against Phyt-ophthora infestans in tomatoes +) 30 46922 -34- Compound according to Concentration (% active substance) the invention 0.005 0.001 Furan-2-carboxylic acid [N-(2-oxoperhydro 100 86 -3-furyl)-2,6-dimethyl-anili dej Furan-2-carboxylic acid [ 2,6-dimethyl-N- 100 86 (5-methyl-2-oxoperhydro-3-furyl)-ani1ide] Furan-2-carboxylic acid [ 2,3-dimethyl-N- 71 — (2-oxoperhydro-3-furyl)-ani1i dej Furan-2-carboxylic acid[ 3-chloro-N-(2- 100 — oxoperhydro-3-furyl)-ani1ide] Furan-2-carboxylic acid [ 3-f1uoro-N-(2- 81 — oxoperhydro-3-furyl)-ani1ide] Agent for comparison Manganese ethylene bisdithiocarbamate 67 0 +) Effect was calculated on 100% attack in the untreated control Example 12 Systemic effect of soil treatment against Phytophthora infestans in tomato plants in a greenhouse In a series of tests the active substances to be tested, which had been weighted out (weight by volume), were mixed with soil which was then placed in plant pots and young tomato plants having at least two developed foliage leaves were placed in these pots. After the expiry of the desired pre-dose time (for example 3,4 or 18 days) the plants were sprayed with an aqueous suspension which contained per millilitre 50,000 to 80,000 sporangia of the fungus indicated in the heading above and which had been 4 6 9 2 2 -35- incubated for approximately 2 hours in a refrigerator at 11°C, The plants were incubated at a high level of air humidity and at approximately 15 to 18°C in a greenhouse and after approximately 5 days the percentage proportion of leaf surface that had been attacked was assessed. The fungicidal effect was calculated as follows: 100 lOOxattack in treated plants attack in untreated plants -=% effect 10 Systemic effect of soil treatment against Phytophthora infestans in tomato plants (Weight active substance/volume) Compound according to the invention ppm active substance 15 %Effect+) of treatment 4 days 18 days before before inoculation inoculation 20 Furan-2-carboxylic acid [n- 25 32 75 (2-oxoperhydro-3-furyl)- 5 10 32 ani1i de ] Furan-2-carboxyl i c acid [j*l- 25 60 92 (2-oxoperhydro-3-furyl)-2,6- 5 27 66 dimethylani1i de J Furan-2-carboxyl ic acid j^2,6- 25 94 100 diniethyl-N-(5-methyl-2- 5 57 95 oxoperhydro-3-furyl)-25 ani1i de ] +) Effect was calculated on 100% attack in the untreated control 46922 -36- Example 13 Curative effect of leaf treatment against Phytophthora infeetans in tomato plants in a greenhouse In a series of tests young tomato plants having at least 2 developed foliage leaves were sprayed with an 5 aqueous suspension which contained per millilitre 50,000 to 80,000 sporangia of the fungus indicated in the heading above and which had been incubated for approximately 2 hours in a refrigerator at 11°C. The plants were incubated at a high level of air humidity. After the 10 expiry lof the desired pre-dose time the plants were sprayed unti-1 dripping wet with the concentration to be tested of the fungicide (indicated in the Table below) within the period of latent fungal attack. After the outbreak of fungal attack in the untreated control plants the 15 percentage proportion of leaf surface that had been attacked was assessed. The fungicidal effect was calculated as follows: lOOxattack in treated plants 100 =%eff ect attack in untreated plants Compound according to % Active %Effect+) of treatment the invention substance before 1 day after sprayed inoculation inoculation Furan-2-carboxylic acid[N- 0.004 100 75 (2-oxoperhydro-3-furyl)-2 ,6- di methyl ani 1 i dej Furan-2-carboxy1ic acid 0.004 100 47 [2 ,6-di methyl-N-(5-methy1 -2-oxoperhydro-3-furyl)-ani 1 i dej 4 6922 -37- Compound according to %Active %Effect+) of treatment the invention substance before 1 day after sprayed Inoculation inoculation Agent for comparison Manganese ethylene bisdithiocarbamate 0.004 91 0 +) Effect was calculated on 100% attack in the untreated control

Claims (85)

46922 -38- WHAT WE CLAIM IS:-
1. A compound of the general formula I (C.H„) r CH-N-CO. (I) 10 in which R-| represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, 1 Rg represents an unsubstituted aromatic hydrocarbon group or an aromatic hydrocarbon group substituted by one or more substituents selected from alkyl groups containing 1 to 4 carbon atoms, alkoxy groups containing 1 to 4 carbon atoms, alkylthio groups containing 1 to 4 carbon atoms, halogen atoms, trif1uoromethyl groups, nitro groups, alkoxycarbonyl groups containing 1 to 4 carbon atoms in the alkoxy parts, • alkylcarbonly groups containing 1 to 4 carbon atoms in the alkyl parts and cyano groups, and n represents 1 or 2. \ 15
2. A compound as claimed in claim 1, wherein represents a 4-6922 -39- hydrogen atom or a methyl or ethyl group and Rg represents a phenyl, methyl phenyl, dimethyl phenyl, ethylphenyl, isopropylphenyl, methoxyphenyl, ethoxyphenyl, methylthiophenyl, fluorophenyl, chlorophenyl, bromophenyl, dichlorophenyl, trifluoromethylphenyl, nitrophenyl, cyanophenyl, methoxycarbonylphenyl , acetyl phenyl or biphenylyl group.
3. Furan - 2 - carboxylic acid^N - (2-oxoperhydro - 3 -furyl) - 2,6 - dimethyl anilide J.
4. Furan - 2 - carboxylic acid [2 - chloro - N - (2 -oxoperhydro - 3 - furyl) - anilide].
5. Furan - 2 - carboxy1ic acid [N - (2 - oxoperhydro - 3 furyl) - anilide].
6. Furan - 2 - carboxylic acid £2,6 - diethyl - N -(2 - oxoperhydro - 3 - furyl) - anilide].
7. Furan - 2 - carboxylic acid £2 - ethyl - 6 - methyl -N - (2 - oxoperhydro - 3 - furyl) - anilide].
8. Furan - 2 - carboxylic acid £2 - methoxy - N - (2 -oxoperhydro - 3 - furyl) - anilide].
9.' Furan - 2 - carboxylic acid £2,6 - dimethyl - N - (5 -methyl - 2 - oxoperhydro - 3 - furyl) - anilide]. 46922 -40- 10 15
10. Furan - 2 - carboxylic acid £ 3,4 - dichloro - N -(2 - oxoperhydro - 3 - furyl) - anilide].
11. Furan - 2 - carboxylic acid [2 - methyl - N - (2 ■ oxoperhydro - 3 - furyl) - anilide].
12. Furan - 2 - carboxylic acid £2,4 - dimethyl - N -(2 - oxoperhydro - 3 - furyl) - anilide].
13. Furan - 2 - carboxylic acid [3,4 - dimethyl - N -(2 - oxoperhydro - 3 - furyl) - anilide].
14. Furan - 2 - carboxylic acid £ 2,3 - dimethyl - N -(2 - oxoperhydro - 3 - furyl) - anilide]-.
15. Furan - 2 - carboxylic acid [3,5 - dimethyl - N -(2 - oxoperhydro - 3 - furyl) - anilide|.
16. Furan - 2 - carboxylic acid [2,4,6 - trimethyl - N (2 - oxoperhydro - 3 - furyl) - anilide].
17. Furan - 2 - carboxylic acid £3 - methyl - N - (2 -oxoperhydro - 3 - furyl) - anilidej.
18. Furan - 2 - carboxylic acid £4 - methyl - N - (2 -oxoperhydro - 3 - furyl) - anilidej.
19. Furan - 2 - carboxylic acid [3 - chloro - N - (2 - 4 0 9 2 2 -41- oxoperhydro - 3 - furyl) - anilide
20. Furan - 2 - carboxylic acid £ 4 - chloro - N - (2 -oxoperhydro - 3 - furyl) - anilide J . .v1-
21. Furan - 2 - carboxylic acid £2 - ethyl - N - (2 - oxoperhydro - 3 - furyl) - anil idej.
22. Furan - 2 - carboxylic acid £N - (2 - oxoperhydro - 3 furyl) - 3 - tri fl uoromethyl ani 1 i dej .
23. Furan - 2 - carboxylic acid [4 - isopropyl - N - (2 -oxoperhydro - 3 - furyl) - anilide |. v- r .
24. Furan - 2 - carboxylic acid 3 - bromo - N - (2 - .-S' -1 oxoperhydro 7 3 - furyl) - anilidej.
25. Furan - 2 - carboxylic acid [4 - methoxy - N - (2 ■ oxoperhydro - 3 - furyl) -'anilide],
26. Furan - 2 - carboxylic acid £4 - ethoxy - N - (2 -oxoperhydro - 3 - furyl) - anilidej.
27. Furan - 2 - carboxylic acid ^4 - ethyl - N - (2 -oxoperhydro - 3 - furyl) - anilide].
28. Furan - 2 - carboxylic aci-d [4 - bromo - N - (2 -oxoperhydro - 3 - furyl) - anilide]. 46922 -42-.
29. Furan - 2 - carboxylic acid [3 - fluoro - N -(2 - oxoperhydro - 3 - furyl) - anilide].
30. Furan - 2 - carboxylic acid j^4 - fluoro - N - (2 -oxoperhydro - 3 - furyl) - anilide]. 5 31. Furan - 2 - carboxylic acid [4 - methoxy - 2 - methyl
31. - N - (2 - oxoperhydro - 3 - furyl) - anilide].
32. Furan - 2 - carboxylic acid Jj?,5 - dimethyl - N -(2 - oxoperhydro - 3 - furyl) - anilide] .
33. Furan - 2 - carboxylic acid ^2 - ethoxy - N (2 -10 oxoperhydro - 3 - furyl) - anilide].
34. Furan - 2 - carboxylic acid ^2,6 - diisopropyl - N -(2 - oxoperhydro - 3 - furyl) - anilide].
35. Furan - 2 - carboxylic acid [3,5 - dichloro - N - (2 - oxoperhydro - 3 - furyl) - anilide]. 15
36. Furan - 2 - carboxylic acid |^3 - chloro - 2 - methyl - - (2 - oxoperhydro - 3 - furyl) - anilide].
37. Furan - 2 - carboxylic acid [5 - chloro - 2 - methyl -N - (2 - oxoperhydro - 3 - furyl) - anilidej.
38. Furan - 2 - carboxylic acid |2 - methoxycarbony1 - N - 46922 -43- (2 - oxoperhydro - 3 - furyl) - anilidej .
39. Furan - 2 - carboxylic acid J^3 - methoxy - N - (2 -oxoperhydro - 3 - furyl) - anilide].
40. Furan - 2 - carboxylic acid [^3 - nitro - N - (2 -5 oxoperhydro - 3 - furyl) - anilidej.
41. Furan - 2 - carboxylic acid |^3 - chloro - N - (5 -methyl - 2 - oxoperhydro - 3 - furyl) - anilidej.
42. Furan - 2 - carboxylic acid^3 - methylthio - N -(2 - oxoperhydro - 3 - furyl) - anilidej. 10
43. Furan - 2 - carboxylic acid £5 - chloro - 2 - methoxy -N - (2 - oxoperhydro - 3 - furyl) - anilidej.
44. Furan - 2 - carboxylic acid £3. - fluoro - N - (5 -methyl - 2 - oxoperhydro - 3 - furyl) - anilidej.
45. Furan - 2 - carboxylic acid £4 - phenyl - N - (2 -15 oxoperhydro - 3 - furyl) - anilidej.
46. Furan - 2 - carboxylic acid £3 - acetyl - N - (2 -oxoperhydro - 3 - furyl) - anilidej.
47. Furan - 2 - carboxylic acid [2 - chloro - 6 - methyl -N - (2 - oxoperhydro - 3 - furyl) - anilidej. ... 1 * ' •■. T' 10 I ■ 40922 -44-
48. Furan - 2 - carboxylic acid [2 - bromo - N - (2 -oxoperhydro - 3 - furyl) - anilidej.
49. Furan - 2 - carboxylic acid [2,3 - dichloro - N -(2 - oxoperhydro - 3 - furyl) - anilidej.
50. Furan - 2 - carboxylic acid ^3 - chloro - 2 - methoxy - N - (2 - oxoperhydro - 3 - furyl) - anilidej.
51. Furan - 2 - carboxylic acid ^3 - ethyl - N - (2 -oxoperhydro - 3 - furyl) - anilidej.
52. Furan - 2 - carboxylic acid £3 - cyano - N - (2 -oxoperhydro - ,3 - ,furyl) - anilidej.
53. A process for the manufacture of a compound as claimed in claim 1, wherein a compound of the general formula II (ch2)n —ch-nh-r2 (II). = 0 R1 15 in which R^ ,R2 and rf have the meanings given in claim 1, is reacted in the presence of an acid-binding agent with a 1 f urancarboxyl i c acid' chloride of the formula III 46922
54. A process as claimed in claim 53, wherein thie reaction is carried out in the presence of a solvent.
55. A process as claimed in claim 53 or 54, wherein the compound of the general formula II and the compound of the formula I'll are used in equimolar proportions.
56. A process as claimed in claim 53, conducted substantially as described herein.
57. A process as claimed in claim 53, conducted substantially as described in any one of Examples 1 to 3 herein.
58. A fungicidal preparation which comprises a compound of the general formula I given in claim 1, in which , R2 and n having the meanings given in claim 1, in admixture or conjunction with a suitable carrier.
59. A fungicidal preparation which comprises a compound as claimed in claim 2, in admixture or conjunction with a suitable carrier.
60. A fungicidal prepartion which comprises the compound claimed in any one of claims 3 to 52, in admixture or 469 22 -46- conjunctlon with a suitable carrier.
61. A preparation as claimed in any one of claims 58 to 60, which is in the form of a powder, a strewable preparation, granules, a solution, an emulsion or a suspension.
62. A preparation as claimed in any one of claims 58 to 61, containing a single compound of the general formula I in an amount of approximately 1 to 80% by weight.
63. A preparation as claimed in any one of claims 58 to 61, containing two or more compounds of the general formula I in a total amount of approximately 1 to 80% by weight.
64. A preparation as claimed in any one of claims 58 to 63, which also contains a single surface-active agent in an amount of up to 20% by weight.
65. A preparation as claimed in any one of claims 58 to 63, which also contains two or more surface-active agents in a total amount of up to 20% by weight.
66. A preparation as claimed in any one of claims 58 to 65, which also contains a dyestuff. !
67. Any one of the fungicidal preparations as claimed in claim 58 and substantially as described in Examples 4 to 11 and 13 -47- 46922 herein.
68. A method of protecting a living plant against phytopathogenic fungi, wherein the living plant is treated with a compound of the general formula I given in claim 1, 5 in which R-j,R2 and n have the meanings given in claim 1.
69. A method as claimed in claim 68, wherein the living plant is treated with a compound as claimed in claim 2.
70. A method as claimed in claim 68, wherein the living plant is treated with the compound claimed in any one of 10 claims 3 to 52.
71. A method as claimed in claim 68, wherein the living plant is treated with a fungicidal preparation as claimed in any one of claims 58 to 65 and 67. |
72. A method as claimed in claim 68, conducted substantially 15 as described in an.y one of Examples 6,8,10,11 and 13 herein.
73. A method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with a compound of the general formula I given in claim 1, in which R-|,R2 and n have the meanings given in claim 1. i 20
74. A method as claimed in claim 73, wherein the crop area is treated with a compound as claimed in claim 2. 4 0922 -48-
75. A method as claimed in claim 73, wherein the crop area is treated with the compound claimed in any one of claims 3 to 52.
76. A method as claimed in claim 73, wherein the crop 5 area is treated with a fungicidal preparation as claimed in any one of claims 58 to 65 and 67.
77. A method as claimed in claim 73, conducted substantially as described in any one of Examples 4,7,9 and 12 herein.
78. A method of dressing seeds, wherein the seeds are 10 treated with a compound of the general formula I given in claim 1, in which and n have the meanings given in claim 1.
79. A method as claimed in claim 78, wherein the seeds are treated with a compound as claimed in claim 2. 15
80. A method as claimed in claim 78, wherein the seeds are treated with the compound claimed in any one of claims 3 to 52.
81. A method as claimed in claim 78, wherein the seeds are treated with a fungicidal preparation as claimed in any one of claims 58 to 67. 20
82. A method as claimed in claim 78, conducted substantially as described in Example 5 herein. 40922
83. A pack which comprises a compound of the general formula I given in claim 1, in which R-j ,R2 and n have the meanings given in claim 1, together with instructions for its use for controlling phytopathogenic fungi. 5
84. A pack as claimed in claim 83, wherein the compound of the general formula I is a compound as claimed in claim 2.
85. A pack as claimed in claim 83, wherein the compound of the general formula I is the compound claimed in any one 10 of claims 3 to 52. Dated the 24th day of May, 1978. CRUICKSHANK & CO. Agents for the Applicants, Youghal House, 13 Trinity Street, Dublin, 2.
IE1028/78A 1977-05-27 1978-05-24 Fungicidally active furancarboxylic acid anilides and their manufacture and use IE46922B1 (en)

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AR (1) AR224234A1 (en)
BG (1) BG28687A3 (en)
BR (1) BR7803217A (en)
CA (1) CA1156665A (en)
CH (1) CH637393A5 (en)
CS (1) CS194200B2 (en)
DD (1) DD136092A5 (en)
DK (1) DK192278A (en)
EG (1) EG13300A (en)
ES (1) ES469811A1 (en)
FI (1) FI781211A (en)
GR (1) GR71669B (en)
HU (1) HU180985B (en)
IE (1) IE46922B1 (en)
IL (1) IL54720A (en)
IT (1) IT1096327B (en)
MX (1) MX5432E (en)
NO (1) NO149431C (en)
NZ (1) NZ187271A (en)
PH (1) PH15611A (en)
PL (1) PL110264B1 (en)
PT (1) PT68085A (en)
RO (1) RO75073A (en)
SU (2) SU727108A3 (en)
TR (1) TR20539A (en)
YU (1) YU97778A (en)
ZA (1) ZA783037B (en)

Also Published As

Publication number Publication date
BG28687A3 (en) 1980-06-16
FI781211A (en) 1978-11-28
CS194200B2 (en) 1979-11-30
SU727108A3 (en) 1980-04-05
CA1156665A (en) 1983-11-08
NO781837L (en) 1978-11-28
TR20539A (en) 1981-10-21
AR224234A1 (en) 1981-11-13
SU725560A1 (en) 1980-03-30
PL207070A1 (en) 1979-02-26
SU725560A3 (en) 1980-03-30
EG13300A (en) 1981-12-31
MX5432E (en) 1983-08-05
PH15611A (en) 1983-02-28
DK192278A (en) 1978-11-28
IE46922B1 (en) 1983-11-02
HU180985B (en) 1983-05-30
IL54720A0 (en) 1978-07-31
IL54720A (en) 1983-07-31
PT68085A (en) 1978-06-01
IT1096327B (en) 1985-08-26
NO149431B (en) 1984-01-09
NO149431C (en) 1984-04-25
BR7803217A (en) 1979-01-16
ZA783037B (en) 1979-06-27
DD136092A5 (en) 1979-06-20
NZ187271A (en) 1980-10-08
YU97778A (en) 1983-01-21
PL110264B1 (en) 1980-07-31
GR71669B (en) 1983-06-20
CH637393A5 (en) 1983-07-29
RO75073A (en) 1980-10-30
ES469811A1 (en) 1978-12-16
IT7823778A0 (en) 1978-05-25

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