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CA1050558A - N-(substituted phenyl)-n-furanoyl-alanine methyl esters and their use in fungicidal compositions and methods - Google Patents

N-(substituted phenyl)-n-furanoyl-alanine methyl esters and their use in fungicidal compositions and methods

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Publication number
CA1050558A
CA1050558A CA223,222A CA223222A CA1050558A CA 1050558 A CA1050558 A CA 1050558A CA 223222 A CA223222 A CA 223222A CA 1050558 A CA1050558 A CA 1050558A
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Canada
Prior art keywords
furan
formula
acid
parts
plants
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA223,222A
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French (fr)
Other versions
CA223222S (en
Inventor
Adolf Hubele
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Novartis AG
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Ciba Geigy AG
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Filing date
Publication date
Priority claimed from CH457274A external-priority patent/CH590608A5/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
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Publication of CA1050558A publication Critical patent/CA1050558A/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • 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
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
    • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Abstract of the Disclosure A microbicidal composition which contains as active substance a compound of the formula I

Description

~35Cl 5S~

The present invention provides compounds of the formula I
CH
R ~ H3 ~ 3 \ CO ~ (I~
CH
wherein R represents hydrogen or methyl, ~a process for the manufacture of these compoundsg also microbicidal compositions which contain these compounds as active substance, as well as a method of using these compounds as microbicides, preferably i for combating phytopathogenic fungi.
' Bacterial diseases and mycoses in useful plants are - helped by two factors. On the one hand, in plant hybridizing , .i it is a primary objective ~o attain an increase in yield and ~-, an in~rovemen~ in qualiby, But in this p~ocess the plants frequently lose some of their naLtural resistance to parasites.
On the other hand, experience has shown that bacteria and harmful fungi have developed over the years a substantial resistance to the known pesticides. There is therefore an urgent need for microbicides that are compatible with the cultivated plants and destroy their direct parasites.
Cultivated plants within the scope o~ the present : invention axe, ~or example9 cereals, maize, rice, vegetables, sugar beet, soya, ground nuts, fruit trees, ornamental plants, but princ~palLy vines, hops, cucumber plants (cucumbers, :',~ ~ ..
~ ~ - 2 -,:,,,; ' ' ,~ . .,.; j .. ,. .. , ~ ... .. .. . .
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, , , . , - .. . .: .. . . . . . .

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~56J ~5~3 marrows, melons), solanaceae, such as potatoes, tobacco and tomatoes, as well as bananas, cocoa and rubber plants.
rhe present invention is based on the surprising observation that it is possible to inhibit or destroy with the compounds of the formula I the fungi which occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of these and related cultures or useful plants and also to protect from such fungi which grow later. The active substances ; are effective against phytophathogenic fungi which belong to the following classes: ascomycetes (e.g. erysiphacea);
basidiomycetes, above all rust fungi; fungi imperfecti; but especially against oomycetes which belong to the class of phycomycetes, e.g~ phytophthora, peronospora9 pseudoperonospora, pythium or plasmopara. In addition, the compounds of the formula I have a systemic actionO They can also be used as seed-dressing agents for protecting seeds ~fruit, tubers, kernels) and plant cuttings from fungus infections as well as from phytopathogenic fungi which occur in the soil.
The N-(substituted phenyl)~N-furanoyl-alanine-2Q methyl esters of the formula I constitute a hither~o unknown class of new microbicidal active substances which are markedly superior in their field of use to the conventional commercial preparations.
Compounds of the formula I are manufactured by a method - 3 ~

~. .

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, : . . : , . :: :
,, . , , . , , , :

~ ~ 5~ ~5 ~
according to the invention, for example by acylation of a compound of the formula II

N~ COOCl13 (II) with furan-(2~carboxylic acid,the acid halide, acid anhydride or ester thereof, in isolated instances also with a furan-~2)-~` carboxy amide (transamidation).
By another method according to the invention it is alsopossible to manufacture the c~mpounds of the formula I by onverting the acyl anilide o~ t~ formula III
.i ~ ~$~ co~ (III) ` CH~

.~' wit~ bu~l lithium or sodium hydride in~o the corresponding alkali salt, which is then reacted with t~e ~-halogenopr~pionic acid methyl ester ko give the desired end product, or else to react ,the anilide of the ~ormula III with the a-halogenopropionic acid methyl ester in the presence o~ an alkali carbonate, e.g.
K2CO3, as proton acceptor, preferably wi~h the additton of ~-cata].ytic amounts of an alkali iodide, e.g. potassium iodide.

, , , . , . , , . ~ . .. .

, . ...
~: - , , , , . :
,, , ,~

~ ~ 5 In the formulae II and III, R represents hydrogen or methyl, the term 'lacid halide" denotes preferably acid chloride or acid bromide and the halogen atom in ~-halogeno-propionic acid methylester is preferalby chlorine or bromine.
The reactions can be carried out in the presence or absence of solvents or diluents which are inert to the reactants.
Examples of suitable solvents or diluents are: aliphatic or aromatic hydrocarbons, e.g. benzene, toluene, ~ylene, petroleum ether; halogenated hydrocarbons, e.g. chlorobenzene, methylene chloride, ethylene chloride, chloroform; ethers and ethereal compounds, e.g. dialkyl ethers, dioxan,tetrahydro-furan; nitriles, e.g. acetonitrile; N,N-dialk~lated amides, e.g. dimethyl formamide; anhydrous acetic acid, dimethyl sulphoxide, ketones, e.g. methyl ethyl ketone, and mixtures of such solvents.
The reaction temperatures are between 0 and 180C~
preferably between 20C and 120C, It is often advantageous to use acid acceptors or condensation agents. Su~able examples are: tertiary amines, e.g. trialkylamines (e.g.
triethylamines), pyridine and pyridine bases, or lnorganic bases, e.g. the oxides and hydroxides, hydrogen carbonates and carbonates of alkali metals and alkaline earth metals, as well as sodium acetate. In the above first manufacturing method i~ is also possible to use a surplus of the respective anlline derivative of the formula II as acid acceptor.

' :

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,, . , , . , : ,: . . : :: : :
, ; ~, , - , . : ,, , , ~, . .

. , , .: ,: . , . ,,', :,,' . ' : ., ', ~, ' . ,: . ' :, , ~5~55~
The process of manufacture which procee~ from compounds o~ the formula II can also be carried out without acid acceptors; in some instances it is expedient to pass in nitrogen in order to expel the hydrogen halide that has formed In other instances it is very advantageous to use dimethyl formamide as reaction catalyst.
Particulars on the manufacture of the intermediates of the ormula II can be inferred from the methods which are generally indicated for the manufacture of aniline-alkane acid çsters in the following publications:
. . .
J. Org Chem.30, 4101 (1965); Tetrahedron 1967, 487;
Tetrahedron 1967, 493.
The compounds of the formula I contain an asymmetrical carbon atom in the propionic acid ester chain and can be resolved into the optical antipodes in the customary -manner.
In this connection, the enantiomeric D-form has the more pronounced microbicidal action.
.
Within the scope of the invention, those c~mpounds, their C~mpQs~tlons andtheir use which refer to the D-configu-ration of the formula I are accordingly preferrred. These D-forms have in ethanol or acetone a negative angle of rotation.
The pure, optical D-antipodes are manufactured, for example, by preparing the racemic compound of the formula IV

:

.

:. . .. . : .. . : ~ .

, , ', , ~ ' .' . ' ' .' ' :~ ' , . ~ ,: ' , .. .

~5¢~5S~3 CH-CGOH (IV) (R ~ H o r CH3 ) , ' ' .
and then reacting this in known manner with a nitrogen-containing, optically active base to give the corresponding salt. The pure D-form is obtained stepwise by frac~ional crystallisa~ion of the salt and subsequent liberation of the acid of the formulaIV which is enriched with the optical D-antipode and, if appropriate, by repetition ~also repetition several times) of the salt formation, crystallisation and liberation of the ~-anilinopropionic acid of the formula IV. From this pure D-form it is then possible to obtain the optical D-configuration of the ester of the formula II in conventional manner, for example in the presence of HCl or H2S04~ with methanol. A
.. . ...
~uitable optically active organic base is, for example, ~-phenylethyl amine.
Instead of fractional recrystallization, it is also possible to obtain the enantiomeric D-form of the formula . .
IV by replacing the hydroxy group in the naturally occurring L~) lactic acid by halogen and react~g this product further with 2,6-dimethy]aniline or 2,3,6-trimethylaniline with reversal of the configuration~
'' ' ' ' , ' ` - --- ~:
:, - 7 _ ,.

', ' ,~ ' '' .' ; .' ' ' ' ' . .' ,':: .' . : ~ ~ ' : ~ 5~ 55 ~
Besides the optical isomerism, when R = CH3, there occurs in the furanoylation of the compound II (or in the reaction of the compound III with ~-halogenopropionic acid methyl ester) an atropisomerism about the phenyl- N~a~is, as a consequence of the steric hindrance of the two radicals additionally introduced at the nitrogen atom of the tr;methyl-aniline. Pr~vided no synthesis is carried out with the aim of isolating pure isomers, compound 2 (the manufacture of which ` is described hereinafter) occurs in the manufacture as a mixture .,, of 4 isomers. However, the better fungicidal action of the enantiomeric D-form (in comparison to the DgL-form or the . L-form) is retained. and is not noticeably affected by the : atropisomerism.
;~ The manufacture of the active substances of the formula I is illustrated by the following Examples 1 and,2, , .: . .
'::

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.
.

~5q~
Example 1 Manufacture of C~13 H3 ~ Il-COOC~13 _ N \ ~ ~

CH3 ~ (compound 1) . ~ .
N~ methoxycarbonylethyl)-N-(furan-(2")-carbonyl)-2,6-di-methylaniline.
With stirring, -12 6 g of furan-2-carboxylic acid - chloride are added dropwise to 18.2 g of N-(l-methoxycarbonyl-ethyl)-2,6-dimethylaniline in 10 ml of anhydrous toluene and 0.2 ml of dimethyl formamide. After the weakly exothermic -reaction has subsided, the reaction mixture is refluxed for 5 - hours and the hydrogen chloride which has formed is completely removed by passing in nitrogen. The solvent is removed and the residue is distilled in vacuo; b.p. 156-168c/o.o6 Torr.
The congealed end product melts between 81 -84 C after recry-stallisation from toluene/petroleum ether. X-ray powder patterns show that the product is polymorphous. One of the two modifi-cations meLts at 85C The enantiomeric D-configuration and it~ primary products have the following physical data:

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.

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, ... .

., : ' ' . . . , - .
' ' ' , ` ' ' . ' , , .:
'. ' , ' ' ~ .
'" ' ', ,'. ' ' . ' , ' ~,"', '. ' , ' ,. . ' ' ' '' ' ' ' ' ' ' :~ , . ' 5~i 3 ~~~ Cll3 (a) D =+ 10, 7 ~ 0, 3 j C=1, 56 % glv in e t:hano l (~H3 CH3 (D) -f orlll ~H-*CH~COOCH3 (a)20= -~29 8 -~ 0,5;C=l,52% g/v in -~e t hano l `.' CH3 ~ ~ -:, .
: CH3 CH ~CH-COOCH3 (D)-form m.p. 102-103 \~ / (a)D ~ -47,0 ~G,7 \CG_ I~J C=1~73~7/o ~/v in ace.one C~3 ; (compound Ia~
' ~. Example 2 :
Manufacture of -CH Cc~13 (compound 2 ) 1 3 H - COOC11~

<~ <`&~3 o . .. .
- lo : : : .. ....

.
.

~ 5(~55~
N~ metho~ycarbonyl-ethyl3-N-(furan-(2")-carbony~2,3,6-tri-methylaniline.
a) A suspension of 51.5 g (0.382 mole) of ~,3,6-trimethyl-aniline, 35.3 g of NaHC03 and 126 ml ~1.15 moles) of 2-bromo-propionic acid methyl est r is stirred for 6 hours at a bath temperature of 130 C, then coQled, filtered from NaBr-salt and distilled. Yield: 67.3 g of ~-(2,3~6-trimethylanilino)-propionic acid methyl ester ~b.p. 144 -146 C/9 Torr.) b) A suspension of 33.5 g (0.152 mole) of the ester obtained according to a) and 18 g (0.17 mole) of sodium carbonate in 200 ml of absolute benzene is treated dropwise with 16.7 ml ~0.17 mole) of furan-2-carboxylic acid chloride at 60 -70 C
and kept thereat for 4 hoursO The reaction mixture is cooled and filtered and the filtrate concentrated. The end product crystallises from isopropyl ether (m.p. 98-102C).
The D-form of compound 2 is obtained as a mixture of ~- atropisomers (~cor~ound 2a) by acylating the D-form of the (2,3,6-trimethylanilino)-p~opionic acid methyl ester with furan - (2)-carboxylic acid or one of its reactive derivatives.
The percentage amount of each of these isomers obtained depends : .
on the respective manufacturing conditions.
The compounds of the formula I can be used with other suitable pesticidal or active substances which promote plant growth in order to improve their activity spectrum.
The cornpounds of the formula I can be used by themselves ~ 11 _ , , . .. . , . . " ~,: . ~,; :; , , . ,, . . : ... . : . ..
, . . .: . . . .. .
;., .: ., :,, ;: . . ' :' ', ,, , ~ , ~ 55 ~
or together with suitable carriers and/or other additives.
Suitable carriers and additives can be solid or liquid and corres-.
pond to the customary substances used in formulation technology, for example natural or regenerated mineral substances3 solvents, . dispersants, wetting agents, stickersg thickeners, binders or fertilisers. The amount of acti~e substance in commercially ; useful compositions is between 0.1 and 90 %.
:. The compounds of the formula I can be applied in the following process forms (the percentages by weight in brackets denote advantageous amounts of active substance):

s.olid forms: dusts and tracking agents (up to 10 %); granules, ~ coated granul~s, impregnated granules and homogenous : granules (1 to 80 %);

liquid forms: a~ active substance concentrates which are dis-persible in water; wettable powders and pastes (25~90 % in the ~ommercial pack, 0 01 to 15 %
in ready for use solution);
emulsion concentrates and concentrated solutions .-(10 to 50 %; 0 01 to 15 % in ready for use solution);
b) solutions (0.1 to 20 %).
: .

'~' " ' ' , ~' "/~' S ' , ',' .' ' '' '' .. ' ' ~ '',,.', . ' , . ', ' , ,. . . . .

5~ 5f~

The active substances of the formula I can be formulat-ed, for example~ as follows:
Dusts: The following substances are used to manufacturfe a) a - 50 % and b) a 2 % dust:
a) 5 parts of active substance 2 95 parts of talcum;
.:.
b) ~ parts of active substance 1 1 part of highly disperse silicic acid 97 parts of talcum.
- .:

The active substances are mixed with the carriers and ground and in this form can be processed to dusts for appli-cation.
, Granules: The following substances are used to manufacture 5 %
~-, granules: -. J
~5 parts of active substance 1 !
0.25 parts of epichlorohydrin 0.25 parts of cetyl polyglycol ether 3.50 parts of polyethylene glycol 91 parts of kaolin (particle size 0.3-0.8 mm).
The active substance is mixed with epichlorohydrin and the , mixture is dissolved in 6 parts of acetone. Then polyethylene glycol and cetyl polyglycol ether are added. The resultant solution is sprayed on kaolin and the acetone is evaporated - 13 _ ';, , ,. , : " i , . ................ , , . i, , .. . . ,,, . ,.: , : , , , , ,: , ~ 5~
in vacuo. Such microgranules are advantageously used for com-bating soil fungi.

We~table powders: The following constituents are.used to manu-facture a) a 70 %, b) a 40 %, c) and d) a 25 % and e) a 10 %
wettable powder:
a) 70 parts of N-(l'-methoxycarbonyl-ethyl)-N-tfuran-(2")-carbonyl~ 2,6-dimethylaniline (active substance la (D-form) according to the present invention) parts of sodium dibutyl nap.thylsulphonate 3 parts of naphthalenesulphonic acid/phenolsulphonic acid/formaldehyde condensate (3:2:1) parts of kaolin -. 12 parts of Champagne chalk.

b) 40 parts of active substance 2 parts of the sodium salt of ligninsulphonic acid 1 part of the sodium salt of dibutylnaphthalenesul-phonic acid 54 par~s of silicic acid.

c) 25 parts of active substance 2a (D-form) 4.5 parts of calcium ligninsulphonate 1.9 parts of a Champagne chalk/hydroxyethyl cellulose mixture (1:1) 14 :

. : :, . : .
. : : :. , 105 parts of sodium dibutylnaphthalene sulphonate 19.5 parts of s;licic acid 19.5 parts of Champagne chalk 28.1 parts of kaolin, .~ .
d) 25 parts of active substance 2 205 parts of isooctylphenoxy-polyoxyethylene-ethanol 1;7 parts of a Champagne chalk/hydroxyethyl cellulose mixture (1:1) . ;i 8,3 parts of sodium aluminium silicate 16.3 parts of kieselgu'nr 46 parts of kaolin.
:
I e) 10 parts of active substance la (D-form) ' ~ 3 parts of a mixture of the sodium salts of satur--, ated fatty alcohol sulphates parts of naphthalenesulphonic acid/Eormaldehyde I condensate 82 parts of kaolin.
The active substances are intimately mixed in suitable mixers with the additives and ground in appropriate mills and rollexs.
Wettable powders of excellent wettability and suspension power are obtained. These wettable powders can bP diluted with water to give suspensions of every desired concentration and can be used in particulax for application to leaves.

., : -.-- lS -Emulsifiable concentrates: The fol~owing substances are used to to manufacture a 25 % emulsifiable concentrate:
parts of active substance 1
2.5 parts of epoxidised vegetable oil parts of an alkylarylsulphonate/fatty alcohol polyglycol ether mixture parts of dimethyl formamide S7.5 parts of xylene.
By diluting such concentration with water it is possible to i manufacture emulsions of every desired concentration which are ~i especially suitable for application to leaves.
., : .

Example 3 ; Action against Phytophthora infestans on Solanum lyccpersicum (tomatoes) Ia) Residual ~reventive action Solanum lycopersicum plants of the "Roter Gnom" variety are infected when 3 weeks old with a zoospore suspension of Phytophthora infestans after they have been sprayed with a broth prepared from the active substance processed to a wettable powder and containing 0.05 % of active substance, and dried.
They are then kept for 6 days in a climatic chamber at 18 to ~.
20C and high humidity, which is produced with an artificial wet fog. After this time typicàl leaf specks appear. Their number and size are the criterion for evaluating the tested subs~ance.

~, .

. .

~ ~ 5~l5 Ib) Curative action "Roter Gnom"tomato plants are sprayed when 3 weeks old w~h a zoospore suspension of the fungus and incubated in a climatic chamber at 18 to 20 C and saturated humidity The humidifying is interrupted ater 24 hours. After the plan~s have been dri~ed, they are sprayed with a broth which contains the active substance formulated as wettable powder in a con-centratior of 0.05 %0 After the spray coating has dried, the plants are again kept in the humid chamber for 4 days. Size and num~er of the typical leaf specks which have occurred during this time are the criterion for evaluating the effectiveness of the tested substances.

~ ~ .
II) Preve~tive-systemic action ,The active substance is applied as wettable powda~ in a concentra~ion of 0.05 % (referred to the volume of the soil) .
to the surface of the soil of 3 week old "Roter Gnom" tomatoes in pots. Three days later the underside of the leaves of the plants are sprayed with a zoospore suspension of Phytophthora :
infestans. The plants are then kept for 5 days in a spray chamber at 18 to 20C and saturated humidity, after which time .~ .
typical leaf specks form.The number size of the specks serve the criterion for evaluating the effectiveness of the tested 8ubstances.

.. , - :.
.

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,, , , . : ~ , . . . ..

' . ' . " ' , ,~ .. ,1,.",.. '.

.

i5~

In these three tes~s, the compounds of the formula X
have a pronounced leaf-fungicidal action, i.eO the fungus in-fection is below 5 %, When the D-forms of the compunds a-re applied, i.e. active substances la and 2a, the fungus infection is below 5 % in all three tests even at rates of application of 0.02 %.
.i .

Example 4 Action a~ainst ~c~smoporara viticola (Bert. et Curt.
~Berl. et De Toni) on vines a) Residual preventive action :i Vine cuttings of the variety "chasselas" were reared in a greenhouse. Three plants in the 10 leaf stage were sprayed with a broth prepared from the active substance and-formulated as a wettable powder. A~ter the coating layer had dried, the plants were infected on the underside of the leaves with the spore suspension of the fungus. The plants were subsequently kept for 8 days in a humid chamber,after which time symptoms Q the disease were visible on the control plants. The number and size of the infected areas on the tested plants served as criterion ~or evaluating the effectiveness of the tested active substances~

b) r~Tat Vine cuttings of the variety "Chasselas" were reared . . . . .

.

0 S~ 5S ~
in a greenhouse and infected in the 10 leaf stage with a spore suspension of Plasmopara viticola on the underside of the leaves.
After they had been kept for 24 hours in a humid chamber, the plants were sprayed with an active s-ubstance broth prepared from a wettable-powder of the active substance. The plants were then kept for a further 7 days in a humid chamber, after which time the symptomsof the disease were visible on the control plants, The number and size of the infectedareas on the treat-ed plants served as criterion for evaluating the effectiveness of the tested substances.
In both th ~e tests of Example 4, the compounds of the formula I exhibit a pronounced fungicidal action in the ~ollowing concentrations:
`i :
i ~ctive SubstanceConcentration Fungus infection in a) and b) 1 0,05 % 0 - 5 %
0,0~ % 0 ~ 5 %
- la 0,02 % 0 - 5 `~/0 -I 2 0,05 % 0 - 5 %
; 0,C2 % 0 - 5 %
2a 0,02 % 0 - 5 %
Control _ 100 %

,` ' ~ .

, . .
~.
.

:, .. " .. , . . , , , , , . ~ .. . . .

, .~,,.,,"., ; .; . .. ..

,.: - ,.. ..
~:.;~ - , : , Action ag inst Pythium debaryanum in Beta vulgaris (sugar beet~
a) Action after soil application The fungus is cultivated on sterile oat kernels and added to a mixture of earth and sand. Flower pots are filled with the infected soil in which sugar beet seeds are then sown.
Immediately after sowing~ the tests prepara-tions formulated as ; wettable powders are poured in the form of aqueous suspensions over the soil (00002 % active substance referred to the volume , 10 of the soil). The pots are then stood for 2-3 weeks in a green-house at 20-24C. The soil is kept uniformly moist by gently spraying it with water. The emergence of the sugar beet plants ~ as well as the number of healthy and sick plants are ascert~ined ; in evaluating the tests.
b) Action after seed treatment application The fungus is cultivated on sterile oat kernels and add-ed to a mixture of earth and sand. Flower pots are filled with the infected soil and sugar beet seeds which have been treated with the test preparations formulated as seed dressing powders are - 20 sown therein ~0.1 % active substance referred to the weight of the seeds). The pots are then stood in a greenhouse for 2-3 weeks at 20-24C. The soil is kept uniformly moist by gently spraying it with water. The emergence of the sugar beet plants as well as the number of healthy and sick plants are ascertained.

. ~ ' .' .

, . . , . . ~ , .
: ,., ' :

~ 5S ~
Under the conditions of both test a) and test b), 85 %
;~ of the sugar beet plants emerged after treatment with one of :~ the active substances 1, La, 2 or 2a and had a healthy appearance. Less than 20 % of the untreated control plants emerged and their appearance was in par~ ~ickly.

~` '.
., ~'"

. .

~, . .

. , .

" , ~, , . ., :
.. . . .

.. .. . .

Claims (10)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Anilides of the formula I

(I) wherein R represents hydrogen or methyl.
2. N-(1'-methoxycarbonyl-ethyl)-N-(furan-(2")-carbonyl)-2,6-dimethylaniline of the formula according to claim 1.
3. N-(1'-methoxycarbonyl-ethyl)-N-(furan-(2")-carbonyl)-2,3,6-trimethylaniline.
4. The enantiomeric D-configurations of the compounds according to any one of claims 1 to 3.
5. A process for the manufacture of compounds of the formula I

(I) wherein R represents hydrogen or methyl, wherein either (a) a compound of the formula II

(II) in which R has the meaning indicated above is acylated with furan(2)-carboxylic acid, the acid halide, acid anhydride or one of the esters or amides thereof, or (b) wherein a furan-(2)-carboxanilide of the formula III

(III) in which R has the meaning indicated above, is reacted initially with butyl lithium or sodium anhydride to give the corresponding alkali salt, which is then reacted with .alpha. -halogenopropionic acid methyl ester, or wherein the anilide of the formula III is reacted with .alpha. -halogenopropionic acid methyl ester in the presence on alkali carbonate as proton acceptor.
6. A process according to claim 5, wherein furan(2)-carboxylic acid chloride or furan-(2)-carboxylic acid bromide is used for the acylation.
7. A process according to claim 5, wherein the reaction with .alpha. -chloro or .alpha. -bromopropionic acid methyl ester is carried out in the presence of an alkali carbonate with the addition of catalytic amounts of alkali iodide.
8. A method of combating phytopathogenic fungi which comprises the use of a compound of the formula I

(I) wherein R represents hydrogen or methyl.
9. A method of combating phytopathogenic fungi which comprises the use of N-(1'-methoxycarbonyl-ethyl)-N-(furan-(2")-carbonyl)-2,6-dimethylaniline.
10. A method of combating phytopathogenic fungi which comprises the use of N-(1'-methoxycarbonyl-ethyl)-N-(furan-(2")-carbonyl)-2,3,6-trimethylaniline.
CA223,222A 1974-04-02 1975-03-27 N-(substituted phenyl)-n-furanoyl-alanine methyl esters and their use in fungicidal compositions and methods Expired CA1050558A (en)

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CH159175A CH603041A5 (en) 1974-04-02 1975-02-10 N-Furoyl-N-aryl-alanine esters

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