LU81703A1 - ACETIC ACID ANILIDE, METHOD FOR PRODUCING THESE COMPOUNDS AND THIS CONTAINING FUNGICIDE AGENT - Google Patents

Description

oUi ikNNü / \ ü. , 1 'Commercial Rechls; .chulr b »·' *

Berlin, the 2nd May 1979

ACETIC ACID ANILIDES, METHOD FOR PRODUCING THESE COMPOUNDS AND THIS CONTAINING FUNGICIDAL AGENT

The invention relates to new acetic acid anilides, processes for the preparation of these compounds and a fungicidal agent for combating phytopathogenic fungi containing at least one of these compounds.

Means for controlling phytopathogenic fungi are already known. Agents of this type which are known in practice are, for example, t-tramethylthiuramide disulfide (DE-PS 642 53 ^) and manganese ethylene bisdithiocarbamate (US Pat. No. 2 5 ^ 4 4θ4). :

The object of the present invention is to develop new fungicides with good activity against leaf and soil fungi. s' i

This object is achieved according to the invention by an agent which is characterized in that it comprises at least one compound of the general formula H C - CH - N - CO - CH - X - R.

2 | | I 2 3 H \ I I R2

2> C C = 0 I

R1 V

contains, in the * _o_ o '£ - board: Dr. Herbsrt Asmis - Or.Christian Brubn Hans-Jürgen Hamann Postal address: SCHERING AG - D-1 Berlin 65 P.O.Box 650311 2 Dr. Heinz Hanns · - Kart Otto Mittetsîenscneïd - Dr. Horst Witzei Pcstschecfc-Konlo: Berlin-West 1175-101. EankîeiîzaM 1D01C010 S Chairman of the Supervisory Board: Df. Eduard v. SchwartzkoDDsn Berliner Commerzbank AG. Berlin. Account Nf. 1C3 7C0o CC. Bank guide line 10 (

i SGI ILhiNÜ AG

: r '_ Commercial Rethlsr.chulz -2-

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iiiii R ^ hydrogen or C ^ -C ^ alkyl, R is an aromatic hydrocarbon radical or one or more, the same or different by C ^ -C ^ alkyl, Cj-C ^ alkoxy, C ^ -C ^ alkylthio , Halogen, trifluoromethyl, nitro, C ^ -C ^ -alkoxycarbonyl or cyano-substituted aromatic hydrocarbon radical, C ^ -Cg-alkyl, halogen-Cj-Cg-alkyl, C ^ -C ^ -alkoxy-Cj-C ^ -alkyl C C2-Cg-alkenyl, C ^ -Cg-alkynyl, C ^ -Cg-alkylcarbonyl, halogen | C 1 -C 6 -alkylcarbonyl, one or more times, identical or different |! distinguished by halogen, C ^ -C ^ -alky, C ^ -C ^ -alkoxy, C ^ -C ^, -

Alkylthio, trifluoromethyl, nitro or amino substituted j _ phenyl or benzyl, the amidino or dimethylthiocarbamoy l: f i group and? ! j _ X oxygen, sulfur, which mean sulfinyl or sulfonyl group.

The compounds according to the invention are surprisingly! - superior to the known agents of the type mentioned above in their action against phytopathogenic fungi and also have i | good plant tolerance and sufficient duration of action. They act in the practically possible i

Application rates are not phytotoxic, so that when they are used; negative influences on the planting mash excluded | are. Thanks to these advantageous properties, these compounds can therefore be used in agriculture or horticulture! ,, · --3-.

1 'Ol n 2 · - Board; Dr. Herbert Asmis · Christian Bruhn - Hans-Jürgen Hamann Postal address: SCHERtNG AG - D-1 Eerlin 65 - Posüaöi £ SC311 z "Dr. Heinz Kannst. Karl Otto Mittelstenscheid · Dr. Horst Witzel pM?« Rh »r * .Kr .ntA- Reriin-w * «» R.mvut »raht ina t-wie

SU! ILI iîNG AG

• * '2 Ge, v «? Ihlic.her R ^ chliüdiutz« fr è Λ can be used for soil and soil treatment or' for leaf application.

The compounds according to the invention are distinguished by an excellent action against a large number of harmful fungi, such as, for example, Pythium, Phytophthora, Plasmopara, Piricula-ria, Botrytis and others.

"Di t.

In contrast to the only preventive means, such as / l

Example manganese ethylene bisdithiocarbamate, the compounds according to the invention have the extraordinary advantage of a curative and systemic action and thus also allow the control of fungi which have already penetrated into the plants.

Of the compounds according to the invention are notable for very good activity, in particular those which are those in formula I given above

R ^ hydrogen, methyl or ethyl, R phenyl, methylphenyl, dimethylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, bromphenyl, dichlorophenyl, trifluoromethylphenyl, methylthiophenyl or cyanphenyl, R ^ methyl, ethyl, propyl, isopropyl, tert-butyl, Allyl, propenyl, propynyl, methoxyathyl, benzyl, chlorobenzyl, methylbenzyl, methoxybenzyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl, acetyl, chloroacetyl and ν X signify oxygen, sulfur, the sulfinyl or the sulfonyl group 5 /. _; t_

Board: Dr.Uerbert AsmisOr.Christian Bruhn - Hans-Jürgen Hamann Postal address: SCHERING AG - D-t Berlin E5 Kainz Hanns · - Karl Otto Mittellenscfteid-Dr. Horst Witzei postal check account: Eeriin-West 1175-101. Eanklei’réhl ÎOOIOOIO

^ Sa *. . . . . «·. ._ _ η _ V * J ______- Λ .. ^ .1 ._______._ t________ ... 11 ..-- r "L -. —— m Λ r *” D A.ltn rt t. _ ej -, ηο, r tt 1 "U 11.:1-.11-JG/'.ü;> i Commercial R '* î.hloT.chulz" * ♦ The compounds according to the invention can be used either alone, in a mixture with one another or with other active ingredients If desired, other fungicides, nematicides, insecticides or other pesticides can be added, depending on the desired purpose.

The active ingredients are expediently in the form of preparations, such as powders, sprinkling agents, granules, solutions,

Emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and, if appropriate, wetting agents, adhesives, emulsifiers and / or dispersing agents.

Suitable liquid carriers are water, mineral oils, or other organic solvents, such as xylene, chlorobenzene, cyclohexanol, dioxane, acetonitrile, ethyl acetate, dimethylformamide, isophorone and dimethyl sulfoxide.

Lime, kaolin, circles, talc, Attaclay and other clays as well as natural or synthetic silica are suitable as solid carriers.

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Board; Dr. Herbert Asmis - Dr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AG0-1 Berlin 65Pox 65C3H

=? D /. Heinz Hanns. Kirl Otto Miltetoensrteïd. Dr. Hear Witiel postal check account: Eeriin-West 1175-101. Eankleitzoh! ICO 10010

. SCHUîiNG AG

I -5— Commercial Rachîischutt ί [! »*!

Examples of surface-active substances are: salts of lignin sulfonic acids, salts of alkylated benzene sulfonic acids, sulfonated acid amides and their salts, poly-ethoxylated amines and alcohols.

^ If the active ingredients are to be used for seed dressing, can also. Dyes are mixed in to give the dressed seed a clearly visible color.

The proportion of the active ingredient (s) on average can vary within wide limits, the exact concentration of the active ingredient used for the compositions mainly depending on the amount in which the compositions are to be used. For example, the compositions contain between about (1 to 80 percent by weight, preferably between 20 and $ 0

Weight percent active ingredient and about 99 "to 20 weight percent liquid solid carrier and optionally up to 20 weight percent surfactants.

»

The agents can be applied in the customary manner, for example by spraying, atomizing, atomizing, dusting, gasifying, smoking, scattering, pouring or pickling.

"// \ 'n'» j Board of Directors: Dr.Herbert AsmisDr. Christian BruhnHans-Jurgen Hamann Postal address: SCHERING AG - 0-13: 0 Eertin E3Postbox £ 3 63 11 Z Dr. Heinz Hanns * - Kart Otto Mitietstenscfceid - Dr. Horst Witzei postal check account: Eeriin-West 1175-131.Bankleîîzah! 13310010. 'SGI ERiNÜ Λ (j!,' '-6 - Gcwerblïch »r Rt-cliîsidi'jli t Ü st * li | The new compounds of the invention can be used for

Create an example using compounds of general | formula

! H C - CH - N - H

I H- ^ I I K

I c = o 2 ii: rî ^ \ />.

I i, with acid halides of the general formula i! . * l I

ΐ Shark - CO - CH - X - R_ III

z 3 optionally in the presence of an acid acceptor dissolved in an organic solvent to react and the

Process products isolated in a manner known per se, where | R., R, R and X have the meaning given above and 12 3 ^ Hai represents a halogen atom, preferably a chlorine atom.

In the event that X is sulfur, the compound according to the invention can also be prepared by firstly teasing the compounds of the general formula II with acid halides; of the general formula i

I 'Hai - CO - CH - Hai IV

.... £ »if necessary in the presence of an acid acceptor ^ dissolved in / an organic solvent, to compounds of the general * cri *“ 7 5, -'- 'ν - / “I: * board: Dr. Herbert AsmisDr. Christian Bruhn - Hans-Jürgen Hamann Postal address: SCHERING AG - D-1C33 Berlin S5 - P.O.Box ¢ 5 0311 Z Dr. Heinz Hanns »Karl Otto Mittelstenscheid · Dr. Horst YVitzel Pcstscheck account: Eerün-V.est 1175-101. Number of bank seats 103 10310

... SCHERING AG

'—Y - Intellectual Property Law for 4'> • my formula

HgC - C - y · - CO - CH2 - Hai j; c μ = o v R> \ / which are then reacted with compounds of the general formula (u) S - R3 or with thiourea of the formula ^ NH2

S = C

Xnh2. in an inert organic solvent under nitrogen * to the desired process products, where R ^, R ^ and R have the meaning given above, B represents an alkali metal atom, preferably sodium, and Hai a halogen atom, preferably chlorine.

i

If appropriate, acid acceptors can be used, for example, organic bases, such as pyridine, triethylamine or Ν, Ν-dimethylaniline, or inorganic bases, such as hydroxides, oxides and carbonates of alkali and alkaline earth metals.

. Organic solvents can be used as solvents. Board of Directors: Df.Herbert Asmis · Dr. Christian BfuhnHans-Jurgen Hamann Postal address: SCHERÎNG AG - D-ICDö Berlin 65 * PO Box € 5 0311 Z Dr. Heinz HannsKarl Otto MiltelstenschaidDr. Horst Witzei * · ·. tr i-. * f- »r« n «

j. . . SCHmiNG AG

* _ —8— Commercial Redilsschulz.

.. medium, such as ether, tetrahydrofuran, benzene, toluene, xylene, ethyl acetate, acetonitrile, dimethylformamide or dimethyl sulfoxide. The reactions are expediently carried out at temperatures between -15 ° C and 1 ^ 0 ° C.

In the event that X represents the sulfinyl or sulfonyl group, the compounds of the general (formula I with X in the meaning sulfur with oxidizing agents such as organic peracids, for example 3-chloroperbenzoic acid!) In an inert organic solvent, for example

Methyl chloride or chloroform, or mixed with inorganic reagents, such as hydrogen peroxide or potassium per-mangtinate, at temperatures between 0 and 100 ° C. in acetic acid. About 2 oxidation equivalents and in the case of sulfonyl compounds about k oxidation equivalents are required to represent the sulfinyl verb charges. * (

The following examples illustrate the preparation of the compounds according to the invention.

EXAMPLE 1 !

Methoxyacetic acid / 2,6-dimethyl-N- (2-oxoperhydro-3-furyl) - anilide7! A mixture of 9.75s (0.0 ^ 7 mol) 3 ~ (2,6-dimethylanilino) -j perhydrofuranon-2, 6.50g (θ, θ6 mol) kethoxyacetyl chloride, f 250 ml toluene and 2 ml dimethylformamide becomes 3 Hours at! c * i Λ s. -9- T v

·. * Board: Or.Herbert Asmls · Dr. Christian Bruhn Hans-Jürgen Hamann Postal address: SCHEBfNC AG - D-l Ssrlin £ 5 - PO box ¢ 5DJII

Z Dr. Heinz Hanns · - Karl Otto Mitlelstensöieid - Dr. Horst Witzel e-o,. . SCI IEhîNQ Af 5 * _ _y_ Commercial Roc}, bithul.-

25 ° C and then stirred for one hour at boiling temperature. 1-Ian then concentrated to dryness in vacuo and digested the solid residue with diisopropyl ether. After the crystals have been suctioned off, the mixture is dried in vacuo at 25.degree. Yield: 11.5 S = SS? O of theory mp: 130 - 131 ° C

{r! EXAMPLE 2

Ace l. Oxyacetic acid- / ~ 2,6-dimethyl-K- (2-oxoperhydro-3-furyl) anilide 7 10.26 (0.05 mol) 3- (2,6-dimethylanilino) perhydrofuranone-2 in 200 ml of toluene are mixed with 6.85 g (0.05 mol) of acetoicy-acetic acid chloride and heated to boiling for one hour. ζ The reaction solution is then evaporated to dryness in vacuo. The remaining oil is crystallized by rubbing with ether. The crystals are suctioned off, washed several times with a little ether and the substance is dried at approx.

25 ° C in a vacuum.

Yield: 12.6¾ g = 82T8% of theory. Mp .: "106 - 108 ° C

* / -10- «- '“ v m - n · *

2 Board: Df.Herbert Asmis - Df.Chrisüan Bruhn - Hans-J ^ en Hamann Poslanscfirilt: SCHERING AG - D-l Eeriin 53 - Posllaöi fcC3U

7 ßf Un! R »f. Ifarl flfto kii! T «hlpn% rh» iirf · Dr. Horst V »Dn.tr Λ.Μτ.ΙΡηηίΑ * Aefl! N.W« «t P.Snlclnîhahl 100 1D010

SCi ERiNG AG

·. '_10- Geweibllchsr Rerchlsschulx BE I S-PXEL 3

Methyl thioacetic acid- / 2,6-diraethyl-N- (2-oxoperhydro-3-furyl) anilide 7 28.17 g (0.1 mol) of chloroacetic acid- / ~ 2,6-dimethyl-N- (2-oxo -perhydro-3-furyl) -anilide 7 are dissolved in 120 ml of acetonitrile, and 6.5 g (0.15 mol) of sodium methylate are added. The mixture is cooled to about -15 ° C. and mixed with stirring; with 22.4 g (0.47 mol) of methyl reacaptan. After the slow one

Warming to 20 ° C to 25 ° C, the mixture is stirred for about 20 hours at this temperature. Then it is taken up with “ethyl acetate / water and the alkaline water phase is separated off. The organic phase is shaken out once with sodium hydroxide solution and then washed neutral. The vinegar phase is dried over magnesium sulfate, filtered off and concentrated in vacuo. The oily residue is vacuum-dried in an oil pump.

Yield: l8 g = 6l, 3 Y1 of theory

I mp: 71-73 ° C

:. / I «-li- s / 2 board; Dr. Herbert Asmis - Dr. Christian Bruhn - Hans-Jûrçen Hamann Postal address: SCHHHÎNG AG · D-l Earün 65 - Posîîacn CSC311 Z Df.Heinx Hanns1 · Karl Oito Mitlelstenssneid · Dr. Hors! Wittol Fostsciiecic account: Eer! In-V.> Si 1175-101. Eankieüxahl ICO IC010

SOI imiNG AG

• _ -11— 'Commercial Rec-bbsdiuiz EXAMPLE 4

Isopropylsulfonyl-acetic acid- / 2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide7 9.64 g (0.03 mol) isopropyl thio-acetic acid- / 2,6-dimethyl-N- (2- oxoperh.ydro-3-f'uryl) -anilide7 are dissolved in 26 ml of chloroform - and 12.08 g (0.07 mol) of 3-chloroperbenzoic acid are added. After stirring for 4 hours at room temperature, a further 6 g (0.035 mol) of 3-chloroperbenzoic acid are added. The mixture is stirred for about 14 hours and the organic phase is shaken out several times with 1 N sodium hydroxide solution, dried over Magnesiun-sul Tat and concentrated in vacuo. The crystals obtained are digested with J.soether and suction filtered.

Yield: 9 S = 84.9 / »of theory mp: 177-185 ° C

EXAMPLE 5 Dime fchyldithiocarbamic acid / 2,6-dimethyl-N- (2-oxoperhvdro-3-furyl) -anilinocarbonyl-methyl 7-ester 8 * 45 g (0.03 mol) chloroacetic acid / 2,6-dimethyl-N- ( 2-oxoperhy-dro-3-fnryl) -anild7 are dissolved in 100 ml of acetonitrile and after the addition of 5. (0.037 mol) sodium dimethyl difhiocarbamate 6. Heated to the boil for hours with the passage of nitrogen. After cooling to about 20-25 ° C, the reaction mixture is poured into 400 ml of water and extracted 3 times with chloroform. The combined chloroform phases are dried over magnesium sulfate and concentrated in vacuo. The crystalline residue § ^ -12- *: u board; Dr. Herbert Asmis. Dr. Christian Bruhn H: rs-Jürgen Hamann postal address; SCHERING AG - D-1 Berlin £ 5Postbox E5C311

. m f \. f_t. ftf aef ΟΗλ ft I air4. fte tä —rat WtfTftl · f. · Ir _ ^ er nr-.i eeae .Al n ..t> t.ti..VI a ^ eOA tA

SCI if: RiNG AG

* "- 12— Commercial law

. ) ï! I is suctioned off, washed with methanol and hot at room temperature dried in vacuo.

'(

Yield: 7t7 S - 70% of theory

Mp: 153-156 ° C

! *! The following compounds according to the invention can be prepared analogously.

! (* \ 1 «(-13-.

c · CT »r **’ c foreland: Dr. Herbert Asmis Dr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERiNG A3 - D-1 Berlin 65Postbox 65 C311 ^ fs l f .t.LI .mma. _ IS ..I Λ il. fc I a. LU .t * ml «. . . _ _ *. i # _ n - —l:. ιικ._. ... .6t.ta.-LI ..A «aa .a üCi'iUwJü Λΰ • '_j« 3_ Commercial R? Ûiir.r.tîiuLz

Name of the connection Physical constant

Methoxyacetic acid- / 3-chloro-N- (2-oxoper-

hydro-3-furyl) anilide. 7 mp: 100-103 C.

Methoxyacetic acid / 2,6-dimethyl-N- (5-

methyl-2-oxoperhydro-3-i'uryl) - anilide. 7 mp -: 113 - ll4 C

Methoxyacetic acid- / N- (2-oxoperhydro-

3-furyl) anilide 7 m.p .: 65-66 C

Methoxyossigsäure- / 3-roethyl-N- (2-oxoper-.

hvdro-3-furyl) anilide7 mp: 115-116 C

{

Methoxyacetic acid / 2,3-dimethyl-N- (2-Q

oxoperhydro-3-f'iiï'yl) ~ anilxd7 m.p .: 105-106 C

Methoxyacetic acid - ^ - fluoro-N- (5-methyl-

2-oxoperliydro-3_; i'u: ryl) -anilide7 m.p .: 75 - 76 C

Methoxyacetic acid- / 3-chXor-N- (5-methyl-Q

2-oxoperhydro-3- ^ uryl) -anilide7 m.p .: 8l - 83 C

Methoxyacetic acid / 2-diethyl-N- (2-oxoper- -

hydro-3-furyl) anilide 7 m.p .: 66-67 C

. Methoxyacetic acid / 2-methoxy-N- (2-oxoperhydro-3-furyl) anilide 7 mp: 95-97 ° C

Methoxyacetic acid / 3-chloro-2-methyl-N- (2-

oxoperhydvo-3-furyl) anilide 7 mp: 106-108 C.

C methoxy acetic acid / 3-cyano-N- (2-oxoperhydro-3-fnryl) anilide7 mp: 93-9 ^ ° C

Acetoxyacetic acid- / 3-methyl-N- (2-oxoper-

hydro-3-f'uryl) -anilide7 mp: 99 ~ 103 ° C

Acetoxyacetic acid / N- (2-oxoperhydro-- 3-turyl) anilide7 mp: 127 - 128 ° C

Acetoxyacetic acid / 3-bromo-N- (2-oxo-

porhydro-3-furyl) -anilide7 mp: 137-138 ° C

Acetoxyacetic acid / 2,3-dimethyl-N- (2-

oxoperhydro-3-f’uryl) anilide7 Mp .: 97 - 9Ö ° C

Acetoxyacetic acid / 3-i’luoro-N- (2-oxo-

perhydro-3-f'u.ryl) -anilide7 m.p .: 96 - S & ° C

2 -14_ ci »c. Board: Dr. Herbert Asrnis · Dr.Christian Eruhn * Hans-Jurgen Hamann Postal address: SCHERING AG · D-1003 Berlin 65 · Postfach 65 C311

\ Dr. Heim HznnseKarl Olto Mitlelstenscheid - Dr. Horst Wittel postal check account: Berlin-West 1175-101. Banklezah! IMlfcoiO

• Chairman of the First Advisory Board «? Dr. Edward v. Schwartzkoooen Berliner Coffifnerzbank AG. Berlin. Kcnto no. 103 7005 G0. B & nkleitzah! 100 <ar

. SüilLNNÜAG

ί · /. Commercial Rechir;: ^ hijU

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Name of the compound Physical constant IAcetoxyacetic acid / 2,6-dimethyl-N- (5- 0

methyl-2-oxoperhydro-3_furyl) anilide7 Mp.î ΐ4θ - l4l C

Acetoxyacetic acid / 2-methyl-N- (2-oxo-0

perhydro-3-f, uryl) -aniKd7 Mp .: 119-120 C.

AcetoxKessigsäure- / 3-chloro-N- (2-oxo-

perhydro-3-furyl) -anilide7 m.p .: 123 "* 24 C

Acetoxyacetic acid / 3-cyan-N- (2-oxo or

- perhydro-3-fnryl) -ani3id7 m.p .: 118-120 C

c

Phenylthioacetic acid- / 2,6-dimethyl-N-; (2-oxoperhydro-3-furylT “a: n-ilid7 m.p .: 103-105 C

Ethylthio-essissäure- / 2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide7 nD2® li5552

Isoprop3rl thio-acetic acid / 2,6-dimethyl-N- (2-oxaperhydro-3-ftiryl) anilide7 nD2® ^ »5 ^ 90 | tert. -Butylthio-acetic acid- / 2,6-dimethyl-j N- (oxoperhydro-3-i * uryl) -anilide7 n ^ 20 1 * 5400 - S- / 3-chloro-N- (2-oxoperhydro-3-fu .ryl) -anilino-carbony3niethyl7-thiur onium-chlorid mp: 190 C (decomp

Dimethyld: Lthiocarbamic acid / 3-chloro-N- (2-oxoperhydro-3-furyl) anilino'-carbonylmethyl7- £ ester mp: 126 C

j Dimethylthiocarbamic acid- / 3-f lu ° r-N- (2-oxo j perhydro-3-furyl) anilinocarbonylmethyl7 "

ester mp: l60 - 6l C

(3-ethylphenylthio) -3-acetic acid / 2,6-dimethyl-N- (2-oxoperhydro-3-fnryl) -aniïd7 η ^ 20 1 * 5950 (benzylthio) acetic acid ~ / 2,6-dimethyl -N- (2-oxoperhydro-3-furyl) anilide7 n ^ 20 1 * 5720 (2-aminophenylthio) acetic acid / 2,6-di-

methyl-N- (2-oxoperhydro-3-f '^ irylJ-anild7 mp: 150-151 ° C

Chloroacetoxyacetic acid c- / 2,6-dimethyl-N-

(2-oxoperhydro-3-fnryl) -aniïd7 m.p .: 115 - ll8 ° C

1L · - - »* - J; Board of Directors: Dr.Herbert AsmisDr. Christian BruhnHans-Jürgen Hamann Postal address: SCHEÜFNG AG - D-1 Eertin 65 - Posltech 65C3 11 i Dr. Heinz HannsKarl Otto Millelslenscheid Dr. Horst Witzei postal check account. Eerlin-West 1175-101. BanWeitzaht itö 10010

SU ERiNG AG

’· 'Gt-warbliciier f.-.- chliscJniiz

Name of the connection Physical constant

Phenoxyacetic acid- / 2,6-dimethyJ-N-

(2-oxoperhydro-3-furyl) anilide7 m.p. : 92-93 ° C

Chloroacetoxyacetic acid- / N- (2-oxoper-

hydro-3-furyl) anilide 7 mp: 64 ° C

Chlorace toxyacetic acid / 3-methyl-N- (2-

oxoperhydro-3 ~ i'u-ryl) -ani2id7 mp: 82-83 ° C

Chloroacetoxyacetic acid- / 3-bromo-K- (2- .. oxoperhydxo-3-furyl) -aniüd7 mp: 12½ - 125 ° C

Phenoxye 5 acetic acid / 3 ~ bromo-N— (2-0x0 -

perhydro-3-puryl) -anihd7 m.p .: ll4 ° C

Phenoxye3sigsäurc- / N- (2-oxoperhydro-. * 1

3-Puryl) -anihd7 'm.p .: 120-121 ° C

Phenoxyacetic acid / 2,3-dimethyl-K- (2-

oxoperhych'o-3-f’uryï) -aniHd7 Mp .: 80 - 82 ° C

Phenoxye. ·! Acetic acid / 3-methyl-N- (2-oxo-

perhydro-3-furyl) -anilLd7 mp: 87-89 ° C

-.Phenoxyacetic acid- / 2-methyl-N- (2-oxo-

perhydro-3-furyl) -aniü.d7 mp: 112-113 ° C

Phenoxyacetic acid- / 3-chloro; c'-N- (2-oxoperhydro-3-furyl) -aniUd7 Mp .: '93 - 95 ° c f _ * Chlorace toxyacetic acid- / 3-chloro-N- (2-

oxoperhydro-3-f ^ iryl) -nnilid7 m.p .: 102-103 ° C

Phenoxyacetic acid- / 2,6-dimethyl-N- (5-_methyl-2-oxoperhydro-3-iP-ryl) -ani3 ^ l7 mp: 142-143 ° C

Chloroacetoxyacetic acid c- / 2,6-dimethyl-K-

(5-methyl-2-oxoperhydro-3-furyl) -anihd7 mp: 94-97 ° C

S- / 2,6-Dimethyl-N- (2-oxoperhydro-3-iuryl) - anïlinocarbonylmethyl7-thiuronium chloride Mp .: 260 C (decomposition) ./ c * - o *? "-16- I:. Board: Dr.Herbert AsmisDr. Christian Bruhn Hans-Jürgen Hamann Postal address: SCHERING AG - Dt Berlin 65Postbox 65 Ç311? Dr. Heinz Hannse - Karl Otto MittelstenscheidDr. Horst Witzal Postal check account: Berlin-West 1175- 101. BanMeitcaht 1C31C010 * __ ·. 1> · I ·... H. ^ j. R * _1. «_» ______ ·· I »s 1 i. In 1 / à -» I.. »<Υ» «<U 1 Ph /

SCHERING AG

• * -lG- Commercial Rothls «i-} iulx *! Name of the compound Physical constant w _ _ - - Ethoxyacetic acid / 2,6-dimethyl-N- 0

(2-oxoperhydro-3-fnryl) -anild7 Fp-ï ° 3 C

Ethoxyacetic acid- / 2,6-dimethyl-N- 0 _ (5 -methyl-2-oxoperhydro-3-fn.ryl) -anilide7 Mp .: 82 - 3 ethoxyacetic acid / 3-chloro-N- (2- 0

oxoperhydro-3-furyl) anilide. 7 Mp .: 100-101 C.

I \ ethoxyacetic acid / N- (2-oxoperhydro-

3-furyl) -anild7 m.p .: 62 - 6½ C.

AthoxyessLgsäure- / 3-brom-N- (2 — oxoper-

j hydro-3-puryl) -anilide7 m.p .: 113-116 ° C

Ethoxyacetic acid / 3-niethyl-N- (2-oxo-

perhydro-3-f’uryl) -anild7 m.p .: 7¾ - 76 C

j ethoxyacetic acid- / 5-chloro-2-methyl-N-

I (2-oxoperhydro-3- ^ uryl) anilide 7 mp 101-103 ° C

I I

; ’Ethoxyacetic acid / 2-chloro-N- (2-oxoper- __ hydro-3-furyl) -anild7: 1.53 ^ 7

Methoxyacetic acid / 2,6-dimethyl-N- (5-I butyl-2-oxoperhydro-3 "i'uryl) -anild7 m.p .: 80 - 8l C

Methoxyacetic acid / 5-chloro-N- (2-oxoper-I hydro-3-furyl) -anild7 »Mp .: 105 - 106 C

The compounds according to the invention are generally almost * colorless, odorless, crystalline bodies or slightly yellowish liquids which are very poorly soluble in water and petrol, but are very soluble in polar solvents such as acetone, dimethylformamide and dimethyl sulfoxide.

/, '-17-

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t! * ^ Board: Dr. Herbert Asmis - Dr. Christian Bruhn * Hans-Jürgen Hamann Postal address: SCHERtWG AG - D-1C9Ö Berlin E3 - P.O.Box £ 50311! i Dr. Heinz Hannse - Karl Otto Mittelstenscheid - Dr. Horst Witzei postal check account: Berlin-West 1175-101, Sankleltzah! 10G10010 «« ._____ n. .. __.... OafliriBr Cnnf-krTKeftlr Carlin tfnn! R..Mr Rïnlt'e * ÎT * hl 11

SGI ILRNÜ AG

’’ ~ 17 ~ Gf.verblîcbbr R-Jibschuls

The starting compounds for the production of the compounds according to the invention are known per se or can be prepared by processes known per se.

The following examples serve to explain the possible uses and the superior fungicidal activity of the invented (longitudinally according to the compounds.

EXAMPLE 6

Limit concentration test in the control of Pythium ultimum 20 'juige powdered active ingredient preparations were mixed uniformly with the soil, which was heavily contaminated by Pythium ultimum. The treated soil was filled into 0.5 liter earthenware bowls and sown without a waiting period per bowl f f 20 seeds of marker peas (Pisum sativum L. convar. Medullary alef.) Of the variety “Wunder von Kelvedon *’. After a cultivation period of 3 weeks at 20-2 ° C in the greenhouse, the number of healthy peas was determined and a root rating (1-4) was carried out.

Active ingredients, application rates and results are listed in the table below.

Root rating: k = white roots without mushroom necrosis 3 = white roots, slight mushroom necrosis 2 = brown roots, already stronger mushroom necroses 1 = strong mushroom necrosis, roots rotten, · / - s -l8- r “.

Ü. “Board: Dr. Herbert Asmis. Df. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AG - D-1 Berlin ESPostbox 65C311 = F Dr.Heinz Hannse - Karl Otto MittellenscheidDr. Horst Witzei postal check account: Berlin-West 1175-101. Bank number 1031010

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SCHERING AG

. 2 2 Commercial calculation 4 EXAMPLE 7

Control of Phytophthora nicotianae var. Nxcotianae Indian pot culture of Sinningia speciosa

Sinningia young plants of the variety 11 Berliner Rot "were potted in * clay pots with a diameter of 11 cm. The pot substrate was a mixture of 1 part peat culture substrate and ^ 1 part compost. After potting, the plants were once with 100 ml of the specified preparation concentration 3 days later, the pots were evenly inoculated with mycelium flakes from a 3-bone-old phytophthora culture.

This was followed by a culture period of 7 bones at 22 to 24 ° C in the greenhouse.

Active ingredients, application rates and results are listed in the table below.

g compound according to the invention plant loss avg.

* after 7 weeks of fresh plants—

Drug conc. Shallow after 7 _____ weeks___ i

Methoxyacetic acid- / 2,6-di- 0.01% 0% 180g; ° · ° 1 * «j. v. · * · / «In 0.0155 0% 176g

Methoxyacetic acid- / N- (2- * ö oxoperhydro-3-furyl) anilide / 0.02% 0% 200g

Control I.

inoculated - 80% 145g

Control II.

not inoculated - 0% l84g 2 L · - -22- «e ψ *

Board: Dr. Herbert Asmîs - Dr. Christian Bruhn - Hans-Jürgen Hamann Postal address: SCHERING AG · D-1C00 Berlin 65- Postfach é5 C311 Z Df. Heinz Hannse - Karl OUo Mittölstenscfteid * 0r. Horst Witzei Ρηςΐ «^ 4ι> -νΑ'Λη» η · ««? C_ «r» i D.nvtai ^^ i mn «mm

. · SCHERING AG

rjo Commercial! -. ' Jtech! S: .i -. Uli i i B EXAMPLE 8. I

Control of Phytophthora parasitica var. Nicotianae j 1 in tobacco culture

Young tobacco plants of the "Havana" variety were placed in clay pots with I ".

; with a diameter of 14 cm. Pot substrate was a mixture of 1 part of peat culture substrate and one part of sandy compost. After potting, the plants were watered once with 100 ml of the stated concentration of preparation. 3 days later, the pots were evenly inoculated with mycelium flakes from a 4-week-old Phytophthora culture.

This was followed by a culture period of 4 weeks at 24 to 26 ° C in the 1 greenhouse.

Active ingredients, application rates and results are listed in the table below.

i (y compound failure according to the invention average.

! fertilizer after 4 weeks fresh plant _ active ingredient concentration__weight after 4 weeks

Methoxyacetic acid- / 2,6-dj.-. 0.01% 0% 215g methyl-Np-methyi ^ -oxo- 0 <02% o * 230g perhydro-3-furyl) -anilxd / J 3 j methoxyacetic acid- / 2,6-di- 0.01% 0% 225g | . 3-fuiyUT: ^ uSrr% dr ° '° -025S *' Control 1.

j inoculated - 100% 0g! ·! Control IX. 1 1-1.— -23-

P Board of Directors: Dr. Herbert Asmls - Dr. Christian BruhnHans-JSrnfm Hamann Postal address: SCHERING AG - D-lCûo Ρ.αγΠπ es. Pn «t!? Aek rtfßSH

not inoculated - 0% 260g; m

SCHERING AG

'' Commercial calculation:: -23- * EXAMPLE 9

Control of Phytophthora capsici in the paprika culture (Capsicum annuuro)

Bell pepper young plants are placed in clay pots with a diameter of 14 cm. The substrate was a mixture of 1 part peat cultivation substrate with 1 part sandy compost. 3 days after potting, the plants were given 100 ml of the specified

Preparation concentration poured once - 3 days later, the pots were evenly inoculated with mycelium flakes from a 4-week-old Phytophthora culture. This was followed by a culture period of 4 weeks at 24 to 26 ° C in the greenhouse.

Active ingredients, application rates and results are listed in the table below.

Compound-plant failure according to the invention dune concentration after 4 weeks (_5 -: -

Methoxyacetic acid- / 2,6-di- 0.01% 20% methyl-N- (2-oxoperhydro- 0.02% 0% 3-furyl) anilide7 0.04% 0%

Methoxyacetic acid- / 3 “cl1l ° r“ 0.01% 40% K- (2-oxoperhydro-3-fti: ryl) - 0.02% 0% anilide7 * 0.04% 0%

Control I.

»-Inoculated - 100%

Control II.

not inoculated - 0% Λ / 3 -24- r)! * Board: Or.Herbert Asmis - Dr.Christian Bruhn · Hans-Jürgen Hamann Postal address: SCHEFtiNG AG · D-1CC0 Berlin £ 5 · Postfach ’£ 5 Mit

I SCHHRINGAG

_. GüwerblitJier RötJilsscSulz -2 h- i.

... EXAMPLE 10

Control of Phytophthora cryptogaea in the pot culture of Senecio cruentus

Cineraria young plants of the variety "Erfurter ZverS, were potted in clay pots with a diameter of 11 cm. Potsf-strnl Kar a mixture of 1 part of peat culture substrate with 1 ^ part of sandy compost. 3 days after the Kurd j 3-week-old phytophora culture was evenly inoculated, and the culture lasted 7 weeks in a greenhouse at 20 to 22 ° C. Active substances, application rates and results are listed in the following table.

Compound-plant failure fertilizer concentration according to the invention after 7 weeks

Metliuxyacetic acid- / 2,6-di- '0.01? » 0j £ f methyl-N- (2-oxoperhydro-3-n no0, n0 / K furyl) anilide7 0.02 / 0 0/0

Methoxyacetic acid / 2,6-di 0.01% x 20/6 methyl-N- (5-methyl-2-oxoper-n 0 / n0 / hydro-3-furyl) -anilide7 * / 0/0

Control I.

inoculated - $ 100 6

Control II.

. - not inoculated - 0 ° / a f -25- i ^ ^ «- \ z Board: Dr. Herbert Asmïs * Dr. Christian Sruhn - Hans-Jürgen Hamann Postal address: SCHERING AG - D-1CX Berlin 65 - Postface 65 03 Z Dr. Heinz HannsKarl Otto MittelstenscheidDr. Horst Witzei postal check account: Eertin-West 1175-lOt. BanWidth 1C01C010

SCHERING AG

- 25 "" Gewfe / blicfc & r RftklsscHuli B E I S P I E'L 11

Dressing of bush poppy seeds

Bush bean seeds (Phaseolus vulgaris var. Nanus) of the "wax best of all" variety were dressed with 20 years of powdered Wirkshoff preparations ) and 25 seeds of bean seed sown per bowl After a cultivation period of 15 days at 19 to 21 ° C. in the greenhouse, the healthy seedlings were determined, i

Active substances, application rate and results are listed in the table below.

/ ^ * (-26- p »o n - * c. · Board: Dr. Herbi’t Asmis - Dr. Christian Bruhn ♦ Hans-Jurcen Hamann Postal address: SCHERING AG · D-1CX Barlin 65 · Postfach 65C311

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SCHERING AG

* _27 ~ Commercial Rtchissüiulz «EXAMPLE 12

Effect of prophylactic leaf treatment Regen Plasmopara viticola on vine plants in the greenhouse

Young grapevine plants with about 5 Lis 8 leaves were sprayed to runoff point with an active ingredient concentration of 0.025 5 “, sprayed with an aqueous suspension of sporangia of the fungus (about 20,000. I per ml) underneath the leaves after the spray coating had dried on, and immediately in the greenhouse inlaxbiert at 22 to 24 ° C and, if possible, water vapor saturated atmosphere.

From the second day onwards, the humidity was reduced to normal level for 3 to k days (30 to 705 70 saturation) and then kept to water vapor saturation for one day.

^ The percentage of area affected by fungus was then noted for each leaf and the average per treatment was calculated as follows to determine the fungicidal effect: 100. Infested in Treated.

100 - Infection ϊΐΐ-Untreated - ', lrtalnS

-28-

PI

01 r>

Board: Dr. Herbert Asm! » Christian BruhnHans-Jürgen Hamann Postal address: SCHERiNG AG - D-1 Berlin S5 - Postfach SSCItt

SCHL! -; iNÜ / \ G

, 'Commercial Redits ^ c / itita -28-

Compounds according to the invention · / ° effect

Methoxyacetic acid / 2,6-dimeth.yl-N- (2- * oxoperhydro-3-furyl) anilide7 100

Methoxyacetic acid / 3-chloro-N- (2-oxo-perhydro ^ -furyl) -anil ± d7 T 100

Methoxyacetic acid / 2,6-dimethyl-N- (5 ~ methyl'-2-oxpperhydro-3-i''uryl) anilide7 100 λ

Methoxyacetic acid / ÄT- (2-oxoperhydro-3-furyl) -aniïd7 100 X _

Methoxyacetic acid / 3-methyl-N- (2-oxo-perhydro-3-fur-yl) -ani3äd7 100 -

Methoxyacetic acid / 2,3-dimethyl-N- (2-oxoperhydro-3-f'uryl) -xlid7 100

Methoxyacetic acid / 3-i'luoro-N- (5-methyl-2-oxoperhydro-3-f'uryl) -aniljd7 · 100! Methoxyacetic acid / 3-chlpr-N ~ (5-methyl-2-oxoperhydro-3-i'uryl) anilide7 100 _acetoxyacetic acid / 2,6-dimethyl-N- (5-methyl-2-oxopei'liydro-3 ~ f uryl) -aniljd7 7¾

Phenylthioacetic acid- / 2,6-dimethyl-N- (2-oxoperhydro-3-furyl) -anilä7 98 C Acetoxyacetic acid- / 2-niethyl-N- (2-oxopyrydro-3-furyl) anil £ L7 7 ^

Acetoxyacetic acid / 2,6-d ± methyl-N ~ (2-oxoperhydro-3-furyl) -aniid. 7 100

Methoxyacetic acid G- / 2-met.liyl-K- (2-oxoper-hydro-3-fviryl) anilide. 7 100

Metlioxyacetic acid / 2-methoxy-N- (2-oxoper-, îvydro-3-furyl) -aniid7 100

MetUoxyessigsäure- / 3 “CÎilor-2-methyl-N- • (2-oxoperhydro-3-furyl) -anllid.7 100

Acetoxyacetic acid / 3-chloro-N- (2-oxoperliydro-3-furyl) anilide7 98 S / '-29- PI / «" £ Board: Dr. Herbert Asmïs · Dr. Christian Bruhn Hans-Jürgen Hamann Postal address : SCHERING AG - D-1CD0 Berlin E5 - Post'ach £ 5 0311 • = J Dr. Heinz Hanr.se · Karl Otto Mittelstenscheid · Dr. Horst Witzei Postal check account: Eeriin-V.'est 1175-lOt. BsnkteitishMOO 1C010 m Vnpe: ««> n) (Bi> rf ·· ii> fe! r-Mrp.i. · n. ßorlinBi1 nnmmftrrhhnlf ΔΠ Partir * Ifftutn-Mr IM 7ΓΛ «Π P ^ nVbiWnSt 1

SCHERING AG

Commercial Rethlr .-. Chulz 4 -29-

Compounds according to the invention '% τ / active substance A c c t oxy e s sigsäure- / 3-cyan-N- (2-oxop er-h.ydro-3-furyl) -anilide7 7¾

Methoxyacetic acid / 3-cyan-N ~ (2-oxoper-hydro-3-f’uryl) anilide7 100 ethylthio-acetic acid / 2,6-dimethyl-N- (2- <.

oxoperliydro-3-furyl) -anilîd7 100

Isopropylthio-acetic acid / 2,6-dimethyl-N- (2-oxoperhydro ~ 3-furyl) anilide.7 100 $ 'm * tert-butylthioacetic acid / 2,6-dimethyl-N- (2nd -oxoperl \ ydro-3-i "uryl) -anilide.7 95

Isopropylsul: fonyl-acetic acid- / 2,6-dimeth.yl- N- (2-oxoperhydro-3 ~ fvuryl) -axiihd.7 100 y i * -30- c »c * n ▼ c Board: Dr. Herbert Asmis - Dr. Christian Bruhn - Hans-Jürgen Hamann Paslanschrilt: SCHERING AG - D-1 Berlin 65Posüach 65 0311

Claims (4)

1. I il * or multiple, identical or different by C ^ C ^ alkyl, ICj-C ^ alkoxy, C ^ C ^ alkylthio, halogen, trifluoromethyl, nitro, C ^ -C ^ alkoxycarbonyl or cyano-substituted aromatic Hydrocarbon radical, j R ^ C ^ -Cg-alkyl, halogen-C ^ Cg-alkyl, C ^ C ^ -alkoxy-C ^ C ^ -alky I Cg-Cg-alkenyl, Cy-Cg-alkynyl, C ^ Cg- Alkylcarbonyl, halogen! C 1 -C 6 -alkylcarbonyl, one or more, identical or different by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4, -; Alkylthio, trifluoromethyl, nitro or amino substituted t phenyl or benzyl, the amidino or dimethylthiocarbamo I group and! X is oxygen, sulfur, the sulfinyl or sulfonyl group i; !; i * I; mean. I /! «/ -31- o i! - -1 "* [a Board: Dr. Herbert Asmis · Dr. Christian Bruhn - H3ns-Jûrgen Hamann Pcsîsnschrilt: SCHERING AG - 0-1C3D Berlin £ 5 · PO Box 650311 c? Dr. Heinz Hannse · Karl Otto Mittelstenscheid - Dr. Hors! V / itzel PnthrheHi.irnntn · R.riin.w.ct SCHLïRiNG AG * Commercial ReoliijStJnulz -31- 4 «» 2- acetic acid amides according to claim 1, wherein R ^ hydrogen, methyl or ethyl, R ^ phenyl, methylphenyl, dimethylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, dichlorophenyl, tri 'fluoromethylphenyl, methylthiophenyl or cyanophenyl, R ^ methyl, ethyl, propyl, isopropyl , tert-butyl, allyl, propenyl, propynyl, methoxyethyl, benzyl, chlorobenzyl, methylbenzyl, methoxybenzyl, acetyl, chloroacetyl and X oxygen, ^ sulfur, which mean sulfinyl or sulfonyl group. < 3-methylthio-acetic acid / 2,6-dimethyl-K- (2-oxoperhydro-3-furyl) anilide7. 6. Dimethyldithiocarbamic acid / 2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilinocarbonylmethyl7-ester 7. Methoxyacetic acid- / 3-chloro-îi- (2-oxoperhydro-3 ~ furyl) -anili d7 { 8. Methoxyacetic acid / 2,6-dimethyl-N- (5-niethyl-2-oxoperhydro-3-furyl) anilide 7 9-methoxyacetic acid / N- (2-oxoperhydro-3-furyl) anilide 7 10. Methoxyacetic acid / 3-methyl-K- (2-oxoperhydro-3-f ^ yl) ~ anilide7 11. Methoxye ss acetic acid / 2,3-dimethyl-K- (2-oxoperhydro-3-furyl) anilide. 7 12. Metlioxyacetic acid / 3-fluorine-K- (5-K ** ethyl-2-oxoperhydro-3-furyl) -anilide7 2 -32- Herbert Asmii Dr. Christian BruhnHans-Jürgen Hamann Postal address: SCHErîNG AG - D-1 Berlin 65Postbox 65 0311 Dr. Heinz HannseKart Otto Mittelstenscheid - Or. Horst Witzei Postal check account: Eeriin-West 117S-101. EankleitsaM 10013010 Î, 'SCHERiHGAC - 32— Dictionary S! i é 13. Methoixryess jLgic acid / 3 "chl ° r" N "(5-methyl-2-oxoperhydro-3-: curyl) -anilide7 l4. MetTioxyacetic acid-y ^ -methyl-N - ^ - oxoper-hydro-3-furyl) anilide7 15. Me t! Ioxye: sigsigsä-ur, e- / 2-rne thoxy-N- (2-oxoper-hydro-3-furyl) -anilide7 Il6. Methoxyacetic acid / 3-chloro-2-methyl-N- (2-oxoperhydro-3-i "uryl) anilide7! 17 · iIethoxyacetic acid- / 3-cyan-N ~ (2-oxoper- ^ îiydro-3-f "uryl) -aniîid7 l8 · Ace'toxyessxgsâure- / 3-riethy3.-N- (2-oxope: r- hydro- 3-i'iryl) -anxlxd7 19 · Acetoxyacetic acid- / ÂT- (2-oxoperhydro-! 3-furyl) -cmilid7 20- Acetoxyessissaure - ^ - Ïrom-K- (2-oxo- []; erhydro-3-i '^ ryl) -anilide7 21 * Ace ±: oxyessigsâ-u: re / 2,3- <1: ΐπιβ · ϋ ^ 1-Ν- (2-oxopei'h.ydro-3-f'U-ryl) anilide. 7 22. Acetoxyessissäure- / 3-fluoro-K- (2-oxo-perhydro-3-furyl) anilide7 2o Axetoxyessigsäure- / 2,6-dimeth.yl-N- (5-THGtlayl-2-oxoperhydro-3 "Î 'uryl) ~ anilid7 {_ 2 ^ Acetoxÿessigsäure- / 2-methyl-N- (2-oxo-perhydro - anild7 "c Ace-Toxiessigsäure- / 3" cî1lor-N- (2-0x0- perhydro-3-i * 'clryl) - aniXid7 26 Acetoxyacetic acid- / 3-cyan-N- (2-oxo-perliydro-3-f'i; iryl) -anild7 2y # Phexylthio-acetic acid .- / 2,6-dimethyX-N- (2-oxoperhydro- 3-iXirylJ-ariilid7 28 Attrxyltliio-acetic acid / 2, é-dimethyl-N- (2-oxopeaxhydro-3-furyl) anilide7 29 ^ Isopropyltîiio-essissHure- / 2,6-dime-tiiyl-N- (2-oxaperhydro-3-furyl ) -an.ilxd7 I / _ -33- t: Board of Directors: Dr. Herbert Asmis - Dr. Christian Bruhn · Hans * J5rgen Hamann Postal address: SCHERING AG · D-1C0Ô Berlin 65 * Postfach * £ 5C3tt Z Hr Helny WanJ1SB »Karl Otto MiHelstenirheirf - no_ Hnr * t Wit7 # l ......... ... .., .... .. __ SCHERING AC * 33 “· Commercial law: ^> m *> 30. tert-Butylthio-acetic acid / 2,6-dimethyl-N- (oxoperhydro-3-furyl ) -an.ilid7 31. S- / 3-chloro-N- (2-oxoperhydro-3-furyl) anilxno-carbonylmethyl7-thiuroniuni-chlorxd 32. Dime thyldithiocai'baminic acid- / 3-chloi’-N- (2- oxo p erhydro - 3 - for yl) - ani 1 ino - c arb ony lmethy l7 -ester · 33 · Dimethylthiocarbamixisäure- / 3-f'luor-ÎT- (2-oxo-p er hydro- 3 - fury1) -ani1ino c arbonylm e thyl7-ester - * ψ _ V 34 «(3“ M®thylphenylth.io) -3-essxgsaure- / 2,6-dx- m <! thyl-N- (2-oxoperliydro-3-furyl) anild? 35 · (Ilcuizylthxo) acetic acid / 2,6-dimethyl-N— (2-oxoperhydro-3-furyl) anilide 7 '36- (2-aminophenylthio) acetic acid e- / 2,6-dimethyl l. hyl-N- (2-oxoperhydro-3-furylJ-aniHl.d7 j- _ 37. Cli-Lox-acetoxyacetic acid- / 2,6-dimethyl-ΓΓ- (2-oxoperhydro-3-furyl) -anild7 3 ^ * Phonoxyacetic acid- / 2,6-dimethyl ~ N- (2-oxoperhydro-3- furyl) -anilide7 chloroacetoxyacetic acid- / N- (2-oxoper-; hytlro-3-i'uryl) -anilide7 C. liQr chloroacetoxyacetic acid- / 3-niethyl-N- (2- oxoperhydro-3-furyl) -aniï7 41. Chloroacetoxyessxgsäure- / 3-'broin-N- (2-oxop erhydro-3-furyl) -anx3id7 42. Phenoxyacetic acid / 3 ~ ^) * 'orn-N- · (2-oxo-perhydro-3-f'uryl) -xxd7 43 · Phenoxyacetic acid / K- (2-oxoperhydro-3-fu.ryl) -aniHid7 44. Ihexoxyessxgsäure- / 2,3-dimethyl-N- (2- oxoperhydro-3-furyl) -anx3id7 45. Phenoxyacetic acid / 3-methyl-N- (2-oxo-perhydro-3-furyl) -aniüd7 ’-34->« e w “m • 4. bU ibhiNG AG Gewetbiîchir * 4 46. Plienoxyessigsäure- / 2-ir.ethyl-N- (2-oxopex'îaydr'o-3-f'ur'yl) -aniHîd7 i 47- phenoxyacetic acid- / 3-chloro-îi- (2-oxo-perhydro-3 ~ f'uryl) -anüd7 48. Chloroacetoxyacetic acid / 3-chloro-N- (2-oxoperhydro-3-i'uryl) anilide7 4. Phenoxyacetic acid- / 2,6-dimeth.yl-N- (5—! Methyl-2 “-oxoperhydro-3 -: ^ uryl) ~ an-i ^ 7 i. 50 · Chlorocetoxyacetic acid- / 2,6-dxrnetbyl-îT— ((5-niethyl-2-oxoperhydro-3-i'uryl) -anxüd.7 51- S- / 2,6-Diraethyl-N “(2-oxoperhydro-3-furyl) - anxlinocarbonylmethyl7-thiuronxun-chlorxd || 32. isopropylsulfonyl-e3sxgsHurc- / 2,6-dimethyX- iî N- (2-oxoperbydro- 3_ ^ ur'yl) -anilxd7 53.ethoxyessX £ acid- / 2,6-dimethyl-N- (2-oxoperhydro- 3-furyl) -anxld7 3¾. Ethoxyacetic acid / 2,6-dimethyl-N- (5 ~ ethyl-2-oxoperhydro-3-furyl) anxlide / 55 · Ethoxyacetic acid / 3-chloro-N- (2-oxoperhydro-3-furyl) anilide7 56 Ethoxyacetic acid / N- (2-oxoperhydro-I 3-furyl) - an ± Id7 5. A'thoxyacetic acid- / 3-l »roni-N- (2-oxoper—] hydxO-3-furyl) -anxlxd7 i .. J '58. Athoxyacetic acid- / 3-diethyl-N- (2-oxo perhydro -3-furyl) -anild7 j 59 «thoxyacetic acid / 5-chloro-2-rneth.yl-ïi— (2-oxoperhydro-3-furyl) -anxlxd7 [1 - 60. Athoxyacetic acid- / 2-chloro-K- (2-oxoper- hydro-3 “furyl) -anild7 Methoxyacetic acid- / 2,6-diïiethyl-K- (5-butyl- 2-oxoperhydro- 3 ~ faryl) - anxld7 ij methoxyacetic acid- / Ç-chloro-N- (2-oxcper- II f hydro-3-fur-yl) -anxîd.7 -35- Herbert AsmisDr. Christian Bruhn Hans-Jürgen Hamann Postal address: SCHERING AGD-iGOO Berlin 65 - P.O.Box 650311 I 7 Dr. Heinz HannseKarl Otto MitleistescheidDr. Horst Witzei PcstschecJc account: Berün-West 1175-101. Number of bank seats 10010010 'SCHERING AG _35— Gewfc / fclichur Rcciits & rJiuLz «r 63. A process for the preparation of new acetic acid anilias according to claims 1 to 62, characterized in that compounds of the general formula HC - CH - N - H 1 1 1 <H> il - o "2 R1 V md l - acid halides of the general Formula Hai - CO - CH2 - X - R III optionally in the presence of an acid acceptor dissolved in an organic solvent to react and the process products isolated in a conventional manner, where R ^, Rg, R ^ and X have the meaning given above and Shark represents a halogen atom, preferably a chlorine atom 6. Process according to claim 63, characterized in that in the case where X is sulfur, compounds of the general formula HC CH - N - H 2 - I 1 I E2 II / \ / c = 0 ai N / ^ initially with acid halides of the general formula; / Hai - CO - CHg - Hai IV .36- i ”Board: Dr. Herbert Asmis - Dr. Christian Bruhn · Hans-Jürgen Hamann Postal address: SCHERING AG · D-1COO Berlin E5 - P.O.Box 65 0311 i D r. Heinz HannsKarl Otio MittelstenscheidDr. Horst jokes! Postsehedr account: Berlin.W.et 1175.101 p.ankl.irrehl lnoinnin. 'SCHERING AG _ ^ 6- Commercial Rcchh.schütz »* 4» "> · optionally in the presence of an acid acceptor dissolved in an organic solvent to form compounds of the general formula HC C - N - CO - CH - Hai 2-- - | 2 R2 ^ CC = 0 V "N» / <, which are then reacted with compounds of the general formula JS - or with thiourea of the formula / NH2 S = C \ nh2 in an inert organic solvent under nitrogen to give the desired Process products xi, where ^ 1 'R2 and R3 d ^ -e ° ken have the meaning given, B is an alkali metal atom, preferably sodium, and shark is a halogen atom, preferably chlorine. 6 5- Method according to claim 631, characterized in that - in the case that X is the sulfinyl or sulfonyl group, compounds of the general formula I ^ -37- φ board: Dr. Herbert Asmis - Dr. Christian Bruhn Hans-Jürgen Hamann Postal address: SCHERING AG * D-1000 Berlin £ 5 - P.O.Box 65 0311 i v Dr. Heinz HannseKarl Otto Mittelstenscheid - Dr. Horst Witze) Postal check account: Berlin-West 1175-10t. Eankieitz number 100 10010 '__ SCHERIN' '. AG Commercial Redmstbuiz «H C - CH - N - CO - CH - X - R ^ | I ^ J HC c = o ”2 1 Rr" V in the R ^, R ^ lind. R ^ have the meaning given above and X means sulfur, reacted with oxidizing agents in a solvent. (<6 6. Fungicidal agent, identified by, a content of at least one compound according to claims 1 to 62. 67. Fungicidal composition according to claim 66 in a mixture with carriers and / or auxiliaries. 68. Fungicidal agent characterized by a content of vinegar. Acid anilides prepared by the processes according to claims 63, 6¾ and 63. 1 c - i. r y v V / v ^ V v \> £ Φ rt R nr 4 ,. ' 3- methoxyacetic acid / 2,6-dxmethyl-N- (2-oxcperhydro-3 ~ furyl) - anilidj- 4. Acetoxyacetic acid / 2,6dimethyl-M- (2-oxoperhydro-3 "f'uryl) - anilide7 · t ~" 4 Board: Dr. Herbert Asmis - Dr. Christian flruhnHans-Jürgen Hamann Postal address: SCHERING AGD-1K »Berlin 65Postbox E5 C311 '* · Γ» · LI ·: · «LI. ··. ·. 1 / - / (Λ »ι ·« _ a.. II...