CH593612A5 - N-Substd. anilides - fungicides and plant growth regulants prepd by acylation or alkylation of an aniline or anilide - Google Patents

Abstract

Anilides of formula (I): (where R1 is halogen, 1-4C alkyl or alkoxy; R2 is H, halogen, 1-3C alkyl or 1-4C alkoxy; R6 H, halogen, or 1-3C alkyl; R6 is H or methyl; provided that the total C atoms in R1,2,5,6 is not >8; X is -CH2- or -CH(CH3)-; R3 is R', R" and R" are H or (m)ethyl; R4 is 1-6C alkyl, 2-5C alkenyl, or 3-7C cycloalkyl opt. substd. by CN or SCN) are plant growth regulators and microbiocides, esp. active against pathogenic fungi.

Description

  

  
 



   The present invention relates to fungicidal compositions containing a compound of the formula I as at least one active component
EMI1.1
 wherein R1 C1-C4-alkyl, Cl-C4 alkoxy, halogen, R2 hydrogen, C1-C3-alkyl, halogen,
EMI1.2
 or -CN, where R ', R "and R"' are independently hydrogen, methyl or ethyl and R4 is C1-C17-alkyl, C2-C1-7-alkenyl or C3-C7-cycloalkyl which is optionally substituted by cyano or rhodano means, as well as the use of these agents to combat phytopathogenic fungi.



   Under alkyl or as the alkyl part of an alkoxy group, depending on the number of carbon atoms specified, for. B.



  to understand the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl or heptadecyl and their isomers such. B. isopropyl, iso-, sec- or tert-butyl, 1-methylbutyl, 2-ethylhexyl, etc. In the case of R4, these alkyl groups can optionally be substituted by cyano or rhodano.



   Under alkenyl, depending on the number of carbon atoms specified, for. B. to understand the following groups:
Vinyl, propenyl, allyl, butenyl, dec-9-en-1-yl, 2-methyl-but2-enyl, heptadec-8-en-i -yl, heptadec-8,1 1 -dien-i -yl, heptadec 8.1 i, i4-trien-l-yl and their isomers. Alkenyl radicals with more than one double bond are therefore included in the scope of the formula. As C3-C7 cycloalkyl, for. B. the following groups in question: cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl.



   The compounds of the formula I have a microbicidal spectrum for protecting crop plants which is very favorable for practical requirements. Cultivated plants include, for example, cereals, corn, rice, vegetables, sugar beets, soy, peanuts, fruit trees, ornamental plants, but above all vines, hops, cucumber plants (cucumbers, pumpkins, melons), Solanaceae such as potatoes, tobacco and tomatoes, as well as banana plants , Called cocoa and natural rubber plants.



   The active ingredients of the formula I can be used to contain or destroy the fungi that occur on plants or parts of plants (fruits, flowers, foliage, stems, tubers, roots) of these and related useful crops, with parts of plants growing later also being spared from such fungi. The active ingredients are active against the phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g. Erysiphaceae); Badidiomycetes, especially rust fungi (e.g. Puccinia graminis); Fungi imperfecti (e.g. Moniliales and Cercospora spp.); but then especially against the Oomycetes belonging to the class of Phycomycetes such as Phytophthora, Peronospora, Pseudoperonospora, Pythium or Plasmopara. In addition, the compounds of the formula I have a systemic effect.

  They can also be used as a dressing agent for the treatment of seeds (fruits, tubers, grains) and plant cuttings to protect against fungal infections and against phytopathogenic fungi occurring in the soil.



   Preferred microbicides are compounds of the formula I in which R1 is methyl, R2 is in the ortho position to the amino group and is methyl, ethyl or chlorine, -X-R3 is the group
CH3 -CH-COOR ', while R4 and R' have the meaning given.



   Among these compounds, those in which R4 stands for a C1-C4-alkyl, C3-C4-alkenyl or C3-C6-cycloalkyl radical are to be emphasized because of their action.



   Within the abovementioned group of compounds, R '= methyl is preferred.



   Another connecting group in which R1 is methyl or ethyl, R2 is in the ortho position to the amino group and is methyl, ethyl or chlorine, -X-R3 is the grouping -CH2-CN or -CH2-CON (R ") (R ' ") represents, while R4, R" and R "'have the meaning indicated, is also suitable for regulating plant growth.



   Plant growth regulation is to be understood primarily as the retarding control of natural plant development, primarily the desirable reduction in plant size, in particular in plant height. This growth reduction is observed in monocotyledonous and dicotyledonous plants, in particular on grasses, cereal crops, soy and ornamental plants.



   The compounds of the formula I are prepared, for example, by acylating a compound of the formula II
EMI1.3
 with a carboxylic acid of the formula III
HO-CO-R4 (III) or its reactive acid derivative, such as. B. acid halide, acid anhydride or ester, in individual cases with one of their acid amides (transamidation).



   In another method, the compounds of the formula I can also be prepared from the acylanilides of the formula IV
EMI1.4
  be converted directly or intermediately into the corresponding alkali salt with butyl lithium or sodium hydride, which is then converted with a compound of the formula V
Hal-X-R3 (V) leads to the desired end product, or from the acylanilides of the formula IV with the compound of the formula V in the presence of an alkali carbonate (such as Na2CO3 or K2CO3) as proton acceptor, preferably with the addition of catalytic amounts of alkali iodine (such as KJ) will.



   In formulas II, III, IV and V, R1 to R4 and X have the meaning given for formula I, while Hal stands for a halogen atom, preferably chlorine or bromine, or another easily cleavable radical. The term acid halide preferably stands for the acid chloride or acid bromide.



   The reactions can be carried out in the presence or absence of a solution or solution which is inert towards the reactants
Diluents are carried out. For example, the following are possible: aliphatic or aromatic
Hydrocarbons such as benzene, toluene, xylenes, petroleum ether; halogenated hydrocarbons such as chlorobenzene, methylene chloride, ethylene chloride, chloroform; Ether and ätherar term compounds such as dialkyl ethers, dioxane, tetrahydrofuran; Nitriles such as acetonitrile; N, N-dialkylated amides such as dimethylformamide; Dimethyl sulfoxide; Ketones such as methyl ethyl ketone and mixtures of such solvents with one another.



   The reaction temperatures are between 0 and
180 "C, preferably between 20 and 1200. In some cases the use of acid-binding agents or



   Condensing agents advantageous. Suitable tertiary amines such as trialkylamines (for example triethylamine), pyridine and pyridine bases, or inorganic bases such as the oxides and hydroxides, hydrogen carbonates and carbonates of alkali and alkaline earth metals and sodium acetate are suitable.



   An excess of the respective aniline derivative of the formula 11 can also serve as the acid-binding agent in the first process.



   The preparation process starting from compounds of the formula II can also be carried out without acid-binding agents, in some cases passing through
Nitrogen to expel the hydrogen halide formed is indicated. In other cases, the addition of dimethylformamide as a reaction catalyst is very advantageous.



   Details of the preparation of the intermediate products of
Formula 11 can be found in the methods as generally given for the preparation of anilinoalkanoic acid esters in the following publications: 1. Org. Chem. 30, 4101 (1965),
Tetrahedron 1967, 487,
Tetrahedron 1967, 493.



   The compounds of the formula I with the meaning
EMI2.1
 have an asymmetric carbon atom (*) and can be split into optical antipodes in the usual way. Here the enantiomeric D-form has the stronger microbicidal effect.



   In the context of the invention, those compounds, their compositions and their use which relate to the D configurations of the formula I are accordingly preferred. These D-shapes usually have a negative angle of rotation when measured in ethanol or acetone.



   To produce the pure optical D antipodes z. B. the racemic compound of the formula VI on which some of the compounds of the formula I are based
EMI2.2
 in which R1 and R2 have the meanings given for formula I, and then reacted in a manner known per se with an N-containing optically active base to give the corresponding salt. By fractional crystallization of the salt and subsequent release of the acid of the formula VI enriched with the optical D-antipode and optionally repetition (including multiple repetitions) of the salt formation, crystallization and release of the α-anilinopropionic acid of the formula VI, the pure D form is gradually obtained. From this can then, if desired, in the usual way, for.

  B. in the presence of HC1 or H2SO4, with methanol or ethanol to produce the optical D configuration of the ester on which the formula II is based, or the amide corresponding to the formula II with the corresponding amine of the formula HN (R ") (R" ') , preferably via the acid halide. As an optically active organic base, for. B. a-phenylethylamine in question.



   Instead of the fractional crystallization, the enantiomeric D-form of the formula VII
EMI2.3
 represent so that the amino group in naturally occurring L-alanine in the presence of z. B. HCI or HBr is diazotized and thus exchanged for halogen with elimination of N2 and retention of the L configuration, then optionally esterified with methanol or ethanol and then with the aniline of the formula VIII
EMI2.4
 converts, with predominantly inversion to the D configurations of the formula VII occurs (J. Am. Chem. Soc. 76, 6056).

 

  The amides with R3 = CON (R "XR" ') can also be represented in this way. Irrespective of the optical isomerism mentioned, atropisomerism about the phenyl -N <axis is generally observed in those cases where the phenyl ring is substituted at least in the 2,6-position and at the same time unsymmetrical to this axis.



   Irrespective of the optical isomerism mentioned, cis / trans isomerism can also occur at the double bond in the case of R4 = alkenyl.



   If no specific synthesis is carried out to isolate pure isomers, a product is normally obtained as a mixture of two optical isomers, two atropisomers, two cis, trans isomers or as a mixture of these possible isomers. The generally more favorable fungicidal effect of the enantiomeric D-form (compared to the D, L-form or the L-form) is retained and is not significantly influenced by the atropisomerism or the cisltrans isomerism.



   The following examples serve to explain the invention in more detail without restricting it. The temperature data relate to degrees Celsius. Unless otherwise stated, when an active ingredient of the formula I is mentioned, which can occur in optically active forms, the racemic mixture is always meant.



   As starting materials of the formula II, for. B. the following in question: (R; in 2-position) R1 R2 -X-R3 physical constant CH3 6-CH3 -CH (CH3) -COOCH3 bp. 98 /0.8 Torr CH3 6-C2H5 -CH (CH3) -COOCH3 Bp 88-90 /0.01 torr CH3 4-CH3 -CH (CH3) -COOCH3 bp 95-100 / 0.02 torr CH3 5-CH3 -CH (CH3) -COOCH3 bp 106-108 /0.1 torr CH3 3 -CH3 -CH (CH3) -COOCH3 bp. 146/5 torr isoC3H7 H -CH (CH3) -COOCH3 bp. 1100 / 0.2 torr isoC3H7 6-isoC3H7 -CH (CH3) -COOCH3 bp. 1050 / 0.5 torr t.C4H9 H -CH (CH3) -COOCH3 bp. 93 /0.07 torr CH3 4-C1 -CH (CH3) -COOCH3 bp. 125-127 /0.07 torr CH3 6-Cl -CH (CH3) -COOCH3 bp. 88-89 / 0.03 torr FH -CH (CH3) -COOCH3 bp 98 /0.15 torr Cl H -CH (CH3) -COOCH3 bp 90-100 / 0.09 torr Br H -CH (CH3) -COOCH3 bp.

   110 /0.01 torr JH -CH (CH3) -COOCH3 bp 1050 / 0.15 torr nC4H90- H -CH (CH3) -COOCH3 bp 1320 / 0.5 torr Cl 5-Cl -CH (CH3) -COOCH3 m.p. 51.5 -54 CH3 6-C2H5 -CH (CH3) -CoNH2 bp 155-1570 / 0.1 torr C2H5 6-C2H5 -CH (CH3) -CONH2 m.p. 71-73 C2H5 6-C2H5 -CH2-CONH2 m.p. 103 -106 C2H5 6-C2H5 -CH2-COOC2H5 bp. 100-103 /0.04 torr C2H5 6-C2H5 -CH2-CON (CH3) 2 waxy CH3 6-CH3 -CH2-CONH2 m.p. 89-91 CH3 6-CH3 -CH (CH3) -CONH2 m.p. 102-103 CH3 6-CH3 -CH (CH3) -CONHCH3 m.p. 75-76 CH3 6-CH3 -CH (CH3) -CON (CH3) 2 b.p. 104-108 /0.02 port R1 R2 -X-R3 physical
1 constant
C2H5 6-C2H5 -CH2-CONHCH3 m.p. 59-61.5
C2H5 6-C2H5 -CH2-CONHC2H5 m.p. 79-80
CH3 6-CH3 -CH2-COOCH3 bp.

   155-160 / 20 Torr
CH3 6-Cl -CH (CH3) -COOC2H5 bp 110-120 /0.3 torr
CH3 6-C2H5 -CH2-COOCH3 bp 168-171 / 30 torr
CH3 6-C1 -CH (CH3) -CONHCH3 m.p. 51-53 Preparation 1
EMI4.1
 (Connection
No. 1) Nw methoxycarbonyl-ethyl) -N-cyclopropylcarbonyl-2,6-dimethylaniline
51.8 g of methyl α- (2,6-dimethylanilino) propionate in 200 ml of abs. Toluene were with stirring at room temperature with 31.3 g of cyclopropanecarboxylic acid chloride in 50 ml of abs.



  Toluene added. After the addition of 2 ml of dimethylformamide manufacturing instruction 2, the mixture was refluxed for two hours and the solvent and the excess cyclopropanecarboxylic acid chloride were then distilled off in vacuo. The remaining oil was caused to crystallize by rubbing with a little petroleum ether. After recrystallization from toluene-petroleum ether, compound no. 1 melted at 84-87.
EMI4.2




  (Connection
No. 2)
N- (1'-methoxy carbonyl-ethyl) -Nvinylcarbonyl-2,6-dimethylaniline
To 166 g of methyl α- (2,6-dimethylanilino) propionate and 70.4 g of pyridine in 600 ml of abs. Toluene were taking good
Stirring at 20 80.6 g of acrylic acid chloride in 150 ml of abs. Toluene was added dropwise. After stirring for 20 hours at room temperature, the precipitated pyridine hydrochloride was filtered off, the solvent was distilled off in vacuo and the remaining oil was then rectified in vacuo; Sdp.



     130-135 / 0.01 Torr (Comp. No. 2).



   The following compounds of the formula I were prepared in this way or by one of the methods given above: Table I (R1 in the 2-position; -X-R3 =
EMI5.1

EMI5.2


<tb> Conn. <SEP> R <SEP> R2 <SEP> R <SEP> Physical
<tb> 1 <SEP> 4 <SEP>. <SEP> constant
<tb> <SEP> 1 <SEP> CH3 <SEP> 6-CH3 <SEP> Smp. <SEP> 84-87 "
<tb> <SEP> 2 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH = CH2 <SEP> Smp. <SEP> 130-1350 / 0.OlTorr
<tb> <SEP> 3 <SEP> CH3 <SEP> 6-OH3 <SEP> CH2CH (CH3) 2 <SEP> 2 <SEP> Sdp. <SEP> 140 /0.01 <SEP> Torr
<tb> <SEP> 4 <SEP> cH3 <SEP> -C (CH3> 3 <SEP> 4-C1 <SEP> -C (CH3) 3
<tb> <SEP> 5 <SEP> CH3 <SEP> 6-CH3 <SEP> -C (CH3) 3 <SEP> Smp. <SEP> 64-67
<tb> <SEP> 3
<tb> <SEP> 6 <SEP> CH3 <SEP> 11 <SEP> -O6N <SEP> 13 (n)
<tb> <SEP> 7 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2SCN <SEP> Smp.

  <SEP> 101-103
<tb> <SEP> 3 <SEP> 2
<tb> <SEP> 8 <SEP> CH3 <SEP> C2 <SEP> 5 <SEP> -C (CH3) 3
<tb> <SEP> 9 <SEP> C1 <SEP> 5-C1 <SEP> -CH2-CN
<tb> <SEP> 10 <SEP> CH3 <SEP> 6-CH3 <SEP> 0113 <SEP> Sdp. <SEP> 108-110 "/ 0.03 Torr
<tb> <SEP> 11 <SEP> CH3 <SEP> 6-CH3 <SEP> -C2H5 <SEP> Smp. <SEP> 78-80
<tb> <SEP> 12 <SEP> CH3 <SEP> 6-CH3 <SEP> -O3117 (n) <SEP> Smp. <SEP> 49-51
<tb> <SEP> 13 <SEP> CH3 <SEP> 6-CH3 <SEP> -C3H7 (iso) <SEP> Smp. <SEP> 122-123
<tb> <SEP> 14 <SEP> CH3 <SEP> 6-C2H5 <SEP> C3 <SEP> (iso) <SEP> Smp. <SEP> 93-95
<tb> <SEP> 15 <SEP> CH3 <SEP> 6-CH3 <SEP> -O61113 (n) <SEP> Sdp. <SEP> 140-142 / 0.05 Torr
<tb> <SEP> 16 <SEP> 0113 <SEP> 6-CH3 <SEP> -C4H9 (iso) <SEP> Sdp. <SEP> 138-140 / 0.03
<tb> <SEP> Torr.
<tb>



   <SEP> 17 <SEP> CH3 <SEP> 6-OH3 <SEP> 5 <SEP> 11 (n) <SEP> Sdp. <SEP>) /0.25 <SEP> Torr
<tb> <SEP> 18 <SEP> CH3 <SEP> 3-CH3 <SEP> -C3H7 (iso) <SEP> Sdp. <SEP> 1330 / 0.4 <SEP> Torr
<tb> <SEP> 19 <SEP> CH3 <SEP> 3-CH3 <SEP> -CH-C2H5 <SEP> 11
<tb> <SEP> 2 <SEP> 5 <SEP> Sdp. <SEP> l36-1420 / 0.03 torr
<tb> <SEP> 02115
<tb>
EMI6.1


<tb> verb <SEP>. <SEP> R <SEP> Physical
<tb> No. <SEP> R1 <SEP> R2 <SEP> R4 <SEP> constant
<tb> <SEP> 20 <SEP> Cl13 <SEP> 6-CH3 <SEP> -CH-C2H5 <SEP> Smp. <SEP> 71-720
<tb> <SEP> 25
<tb> <SEP> 02115
<tb> <SEP> 21 <SEP> cll3 <SEP> 6-C1 <SEP> -CH3 <SEP> Sdp. <SEP> 123 /0.07 <SEP> Torr
<tb> <SEP> 22 <SEP> CH3 <SEP> 6-C1 <SEP> -C3617 (n) <SEP> Sdp. <SEP> 170 / 0.04 <SEP> Torr
<tb> <SEP> 23 <SEP> CH3 <SEP> 6-C1 <SEP> -CEl-C2H5 <SEP> Stnp. <SEP> 70-71
<tb> <SEP> 25
<tb> <SEP> 02115
<tb> <SEP> 24 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH-C2H5 <SEP> Sdp.

  <SEP> 135-136 / O, l Torr
<tb> <SEP> 02115
<tb> <SEP> 25 <SEP> CH3 <SEP> 6-C1 <SEP> 03117 (150) <SEP> Smp. <SEP> 90-930
<tb> <SEP> 26 <SEP> isoC3H7 <SEP> H <SEP> C3H7 (iso) <SEP> Smp. <SEP> 62-640
<tb> <SEP> 27 <SEP> isoC3H7 <SEP> 11 <SEP> -CH-C2ll5 <SEP> Smp. <SEP> 74-760
<tb> <SEP> 25
<tb> <SEP> 28 <SEP> n04119-0-1 <SEP> 11 <SEP> -03H7 (iso) <SEP> Sdp. <SEP> 152 / 0.05 <SEP> Torr
<tb> <SEP> 29 <SEP> n04119-O-l <SEP> 11 <SEP> -CH-C2H5 <SEP> Sdp. <SEP> 145 /0.05 <SEP> Torr
<tb> <SEP> 02115
<tb> <SEP> 30soC3H7 <SEP> j-isoCII. <SEP> -03117 (iso) <SEP> Sdp. <SEP> 133 /0.1 <SEP> Torr
<tb> <SEP> 31 <SEP> isoC3H7 <SEP> FisoC3H <SEP> -CH-C2H5 <SEP> Sdp. <SEP> 1470 / 0.03 <SEP> Torr
<tb> <SEP> 21152 <SEP> 5
<tb> <SEP> 32 <SEP> isoC3H7 <SEP> SisoC3H <SEP> -051111 (n) <SEP> Sdp. <SEP> 143 /0.03 <SEP> Torr
<tb> <SEP> 33 <SEP> F <SEP> H <SEP> 11 <SEP> 03117 (150) <SEP> Sdp.

  <SEP> 118-122 / 0.35 Torr
<tb> <SEP> 34 <SEP> F <SEP> H <SEP> 9 (iso) <SEP> Sdp. <SEP> 1050 / 0.04 <SEP> Torr
<tb> <SEP> 35 <SEP> CH3 <SEP> 5-CH3 <SEP> -CH = CH-CH3 <SEP> m.p. <SEP> 80-82
<tb> <SEP> 36 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH = C (CH3) 2 <SEP> Sdp. <SEP> 1180 / 0.07 <SEP> Torr
<tb> <SEP> 37 <SEP> CH3 <SEP> 5 <SEP> C2H5 <SEP> -CH = CH-CH3 <SEP> Sdp. <SEP> 130 <SEP> -1320 / 0.05 Torr
<tb> <SEP> 38 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH = C (CH3) 2 <SEP> Sdp. <SEP> 1280 / 0.07 <SEP> Torr
<tb> <SEP> 39 <SEP> 02115 <SEP> 6-C2H5 <SEP> -CH = CH-CH3 <SEP> Sdp. <SEP> 136-1380 / 0.04Torr
<tb>
EMI7.1


<tb> Verb. <SEP> &verbar; <SEP> R <SEP> t <SEP> R <SEP> R <SEP> Physical
<tb> No. <SEP>. <SEP> 1 <SEP> 2 <SEP> 4 <SEP> Cons <SEP> aunt
<tb> <SEP> 40 <SEP> &verbar; <SEP> C2H5 <SEP> h <SEP> C2H5 <SEP> -CH = C <SEP> (<SEP> CH3) <SEP> 2 <SEP> Sdp <SEP>.

  <SEP> 135 <SEP> <SEP> /0.07 <SEP> Torr
<tb> <SEP> 41 <SEP> CH, <SEP> H <SEP> - <SEP> oil
<tb> <SEP> 42 <SEP> CCH <SEP> 1 <SEP> H <SEP> -CH = CH-CH3 <SEP> Sdp. <SEP> 1300 / 0.05 <SEP> Torr
<tb> <SEP> 43 <SEP> CH3-0- <SEP> 11 <SEP> -CH = CH2
<tb> <SEP> 3 <SEP> 2 <SEP> Sdp. <SEP> 138-l390 / 0.02 Torr
<tb> <SEP> 44 <SEP> CH3 <SEP> 5-C11 <SEP> -CH = CH-CH3 <SEP> Sdp. <SEP> 122-1230 / 0.05Torr
<tb> <SEP> 3
<tb> <SEP> 45 <SEP> Cl13 <SEP> 5-C3 <SEP> 1 <SEP> -C11 = C (0113) 2
<tb> <SEP> 45 <SEP> 0113 <SEP> 5 <SEP> -CH <SEP> Sdp. <SEP> 1470 / 0.09 <SEP> Torr
<tb> <SEP> 46 <SEP> CH3 <SEP> j-C1 <SEP> -011 = C (0113) 2 <SEP> Sdp. <SEP> 1410 / 0.03 <SEP> Torr
<tb> <SEP> 47 <SEP> 0113 <SEP> 6-C1 <SEP> t <SEP> -CH = CH-CH3 <SEP> Smp. <SEP> 106-1130
<tb> <SEP> 48 <SEP> l <SEP> cit13 <SEP> 4 <SEP> CII3 <SEP> -CH = C (Cl13) <SEP> 2 <SEP> Sdp.

  <SEP> 129-131 <SEP> / () <SEP>, 03 <SEP> Torr
<tb> <SEP> 4 <SEP> isoC3117jH <SEP> I <SEP> -CIl = C (CH3) <SEP> 2 <SEP> Sdp. <SEP> 129-L31 "/0.03Torr
<tb> <SEP> 50 <SEP> CK, <SEP> -CH3 <SEP> 1 <SEP> -CH2 <SEP> -0112-011 = C112 <SEP> Sdp. <SEP> l43-1450 / 0.04 Torr
<tb> <SEP> 51 <SEP> IisoC3H7 <SEP> j <SEP> H <SEP> -CH = CH-CH3 <SEP> Sdp. <SEP> 142 "/0.3 <SEP> Torr
<tb> <SEP> 52 <SEP> C <SEP> 3 <SEP> 1 <SEP> 3 <SEP> -CH = C (CEI <SEP> 2 <SEP> Sdp. <SEP> 147o / 0.35 <SEP> Torr
<tb> <SEP> 53 <SEP> C4119 <SEP> -o-! <SEP> H <SEP> -CH = C (CH,) <SEP> Sdp. <SEP> 1600 / 0.05 <SEP> Torr
<tb> <SEP> 54 <SEP> H <SEP> H <SEP> CH = C-CH = CH-CH3 <SEP> Sdp. <SEP> 1570 / 0.05 <SEP> Torr
<tb> <SEP> 55 <SEP> 1 <SEP> isoC3H7, <SEP> 6-isoC3H7 <SEP> -CH = CH-CH3 <SEP> Sdp. <SEP> 140 /0.1 <SEP> Torr
<tb> <SEP> 56 <SEP> isoC3117 <SEP> -iso117 <SEP> -cH = c (cH3) <SEP> 2 <SEP> Sdp.

  <SEP> 1700 / 0.1 <SEP> Torr
<tb> <SEP> 57 <SEP> F <SEP> H <SEP> -CH = C (CH3) <SEP> 2 <SEP> zu2 <SEP> Sdp. <SEP> 1250 / 0.3 <SEP> Torr
<tb> <SEP> 58 <SEP> F <SEP> H <SEP> -CH = CH-CH3 <SEP> Sdp. <SEP> 126-1310 / 0.35 Torr
<tb> <SEP> 59 <SEP> C1 <SEP> H <SEP> -CH = C (CH3) <SEP> 2 <SEP> Sdp. <SEP> 118-1220 / 0.05Torr
<tb> <SEP> 60 <SEP> Br <SEP> 11 <SEP> -Cll = C (CtI3) <SEP> 2 <SEP> Sdp. <SEP> 1400 / 0.04 <SEP> Torr
<tb> <SEP> 61 <SEP> Br <SEP> H <SEP> -CH = CH <SEP> -CH3 <SEP> Sdp. <SEP> 1380 / 0.04 <SEP> Torr
<tb> <SEP> 62 <SEP> | <SEP> C1 <SEP> H <SEP> -CH = CH-CH3 <SEP> Sdp. <SEP> 132 "/0.01 <SEP> Torr
<tb> <SEP> 63 <SEP> -C <SEP> 1 <SEP> 6-01 <SEP> Sdp. <SEP> 140 <SEP> - <SEP> 142 <SEP> <SEP> /0.04Torr
<tb> <SEP> 64 <SEP> -CH3 <SEP> 4-CH3 <SEP> Sdp. <SEP> Sdp.138-140 "/0.05Torr
<tb> <SEP> 65 <SEP> -CH3 <SEP> 5-CH3 <SEP> Sdp. <SEP> 137-1380 / 0.07 Torr
<tb>
EMI8.1


<tb> verb.

  <SEP> | <SEP> R <SEP> R <SEP> R <SEP> Physical
<tb> No. <SEP> R1 <SEP> R2 <SEP> R4 <SEP> constant
<tb> 66 <SEP> C2115 <SEP> 5 <SEP> Smp. <SEP> 43.450
<tb> <SEP> 67 <SEP> CH, <SEP> I6O2H5 <SEP> Smp. <SEP> 71-760
<tb> <SEP> Sdp. <SEP> 142 <SEP> /0.03 <SEP> Torr
<tb> <SEP> 69 <SEP> 4 <SEP> 9., <SEP> t <SEP> zip <SEP> Sdp. <SEP> 150-152 / 0.1 <SEP> Torr
<tb> <SEP> 70 <SEP> pCCH9-O <SEP> 11 <SEP> <<SEP> Sdp. <SEP> 149-1510 / 0.04Torr
<tb> <SEP> 71 <SEP> soC3117 <SEP> <j <SEP> Sdp. <SEP>.; dp. <SEP> 135 /0.03 <SEP> Torr
<tb> <SEP> 72 <SEP> isoC3H7 <SEP> bis) <SEP> C317 <SEP> i <1 <SEP> Sdp. <SEP> 138 /0.03 <SEP> Torr
<tb> <SEP> a> 9117
<tb> <SEP> 73 <SEP> F <SEP> 11 <SEP> Sdp. <SEP> 125 "j0.03 <SEP> Torr
<tb> <SEP> 74 <SEP>! <SEP> C1 <SEP> j <SEP> H <SEP> 2 <SEP> Sdp. <SEP> j <SEP> dz. <SEP> 1400 / 0.06 <SEP> Torr
<tb> <SEP> 75 <SEP> J <SEP> 11 <SEP> H <SEP> to <SEP> Sdp.

  <SEP> 1430 / 0.15 <SEP> Torr
<tb> <SEP> 76 <SEP> 0113 <SEP> 6-CH, C) <SEP> Smp. <SEP> 92.960
<tb> <SEP> 77 <SEP> CH3 <SEP> 6-CH3 <SEP> G <SEP> Smp <SEP> 116.1210
<tb> <SEP> 78 <SEP> CH3 <SEP> 6-C1 <SEP> - <SEP> Smp. <SEP> 105.1080
<tb> <SEP> 79 <SEP> j <SEP> 0113 <SEP> 6CH3 <SEP> 3 <SEP> Smp. <SEP> 138-140
<tb> <SEP> 80 <SEP> C113 <SEP> | <SEP> 6-C1 <SEP> {f) <SEP> m.p. <SEP> 129-130.50
<tb>
EMI9.1


<tb> link <SEP> | <SEP> R <SEP> R2 <SEP> t <SEP> Physical
<tb> No. <SEP> 1 <SEP> 2 <SEP> 4 <SEP> constant
<tb> 81 <SEP> CH3 <SEP> 6-C2115 <SEP> e <SEP> Smp. <SEP> 125l27o
<tb> 82 <SEP> nC4H9¯ ¯ <SEP> H <SEP> H <SEP> m.p. <SEP> 73-74.5
<tb> 83 <SEP> 3 <SEP> 13-CH3 <SEP> - <SEP> To <SEP> Smp. <SEP> 51-54 "
<tb> <SEP> 84 <SEP> isoC3TI7 <SEP> H <SEP> Q <SEP> Sdp. <SEP> 145 /0.04 <SEP> Torr
<tb> <SEP> 85 <SEP>; ¯ertC2 <SEP> M0 <SEP> H <SEP> J <SEP> to <SEP> Sdp.

  <SEP> 152.1550 <SEP> /0.06Torr
<tb> <SEP> 86 <SEP> J <SEP> coli3 <SEP> 4-CtI3 <SEP> | <SEP> 4 <SEP> ZSmp. <SEP> 69-72
<tb> <SEP>
<tb> <SEP> 87 <SEP> F <SEP> 11 <SEP> Q <SEP> to <SEP> Sdp. 1320 / 0.05 <SEP> Torr
<tb> <SEP> 88 <SEP> Br <SEP> i <SEP> H <SEP> | <SEP> <<SEP> j <SEP> Sdp. <SEP> 135-1450 / 0.05 Torr
<tb> <SEP> 89 <SEP> C1 <SEP>! <SEP> H <SEP> 11 <SEP> Stnp. <SEP> 102-104
<tb> <SEP> 90 <SEP> 0113 <SEP> 4-CH3 <SEP> CH2 <SEP> -0112-SCN <SEP> Smp. <SEP> 68-720
<tb> <SEP> 91 <SEP> CH <SEP> 5-CH3 <SEP> 1 <SEP> -CII2SCN <SEP> l <SEP> Smp. <SEP> 86-88 "
The following compounds of the formula I are also prepared according to the type of preparation instructions 1 and 2 or using one of the methods given above: Table II (R1 in the 2-position).
EMI10.1


<tb>



  packed <SEP> R <SEP> R2 <SEP> -X-R. <SEP> R, <SEP> IPhysical
<tb> <SEP> No. <SEP> 1 <SEP> 3 <SEP> Y <SEP> I constant
<tb> <SEP> 93 <SEP> CII3 <SEP> 6-CH3 <SEP> CH? CNW, <SEP> Smp. <SEP>) <SEP> 3 <SEP> C (CH3) <SEP> 3 <SEP > | Smp. <SEP> 175-177
<tb> <SEP> 2 <SEP> 3 '
<tb> <SEP> 94 <SEP> C2Tg <SEP> 6 <SEP> C21I52 <SEP> CONH, <SEP> -Y13 <SEP> Smp. 140,5-143 "
<tb> <SEP> Smp. <SEP> 140 <SEP>, 5143o
<tb> <SEP> 94 <SEP> 02115 <SEP> 6-0 <SEP> 11 <SEP> -011 <SEP> -C0NH
<tb> <SEP> 25 <SEP> 2 <SEP> 2
<tb> <SEP> 95 <SEP> C113 <SEP> 6-CH3 <SEP> -0111-00N (011) 2 <SEP> -CH = C (CH3) 2 <SEP> Sdp.115-1200 /
<tb> <SEP> 0113 <SEP> 0, OSTorr
<tb> <SEP> 96 <SEP> 0113 <SEP> 6 <SEP> -C11-00M1C113 <SEP> 011 = 011C113 <SEP> Srnp.

  <SEP> 114.1150
<tb> <SEP> 0113
<tb> <SEP> 97 <SEP> CH3 <SEP> 6 <SEP> CI, <SEP> - <SEP> 6.0113 <SEP> 3 <SEP> <<SEP> Smp. 131-134
<tb> <SEP> 0113
<tb> <SEP> 98 <SEP> CH3 <SEP> 6 <SEP> -CH3 <SEP> C <SEP> 3 <SEP> -CH = CH <SEP> -CH3 <SEP> Smp <SEP>. <SEP> 14 <SEP> 9 <SEP> -150
<tb> <SEP> 0113
<tb> <SEP> 99 <SEP> CH <SEP> 6 <SEP> CH3 <SEP> 6-C1 <SEP> -CH <SEP> -COOC2H5 <SEP> .011 = 0 (0113) 2 <SEP> Sdp .146-150
<tb> <SEP> 0113
<tb> 100 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOC2H5 <SEP> -CH = CH-CH3 <SEP> Smp. 88-92 "
<tb> <SEP> 01113 <SEP> LJ <SEP> J
<tb> 101 <SEP> 02115 <SEP> 6.02115 <SEP> -CH2 <SEP> -COOCH3 <SEP> -Cll = CH <SEP> -CH3 <SEP> Smp. 55-570
<tb> 102 <SEP> 02115 <SEP> 6.02115 <SEP> -CH2-COOCH3 <SEP> 0 (0113) 3 <SEP> Smp. 72.5-73
<tb> <SEP> 103 <SEP> 02115 <SEP> 6 <SEP> -C2H5 <SEP> -CH-CONH2 <SEP> 0113 <SEP> Smp. 141-142
<tb> <SEP> 0113
<tb> <SEP> 104 <SEP> 02115 <SEP> 602ll5 <SEP>

   -CH2-CON1lC113 <SEP> -CH3 <SEP> mp 123-1240
<tb>
EMI11.1


<tb> Connection <SEP> R <SEP> 1 <SEP> R <SEP> 2 <SEP> -X-R <SEP> R <SEP> physical
<tb> No. <SEP> 1 <SEP> 2 <SEP> 3 <SEP> 4 <SEP> constant
<tb> <SEP> 105 <SEP> 02115 <SEP> 6.02115 <SEP> -CH2-CONHCH3 <SEP> -C (CH3) <SEP> 3 <SEP> mp 183-1840
<tb> <SEP> 106 <SEP> 02115 <SEP> 6-C2H5 <SEP> -CH2-CON (CH3) <SEP> 2 <SEP>% <SEP> 1 <SEP> Smp <SEP> Smp. <SEP > 71-74 "
<tb> <SEP> 107 <SEP> C2Hg <SEP> 6 <SEP> 02115 <SEP> 6-C2} l5 <SEP> -CH2-CON (CH3) 2 <SEP> e <SEP> nD <SEP> 1.6859
<tb> <SEP> 108 <SEP> C2ll5 <SEP> 6 <SEP> 02115 <SEP> 6C2J5 <SEP> '<SEP> CON <SEP> (C) <SEP> CH, <SEP> Smp <SEP>.

  <SEP> 137 <SEP> -139
<tb> <SEP> 109 <SEP> 025 <SEP> 6 <SEP> -C2t15 <SEP> -CH2 <SEP> -COOCH3 <SEP> Sdp.l32 <SEP> 132-134 "
<tb> <SEP> 0.03 torr
<tb> <SEP> 110 <SEP> 02115 <SEP> 6 <SEP> C2 <SEP> 5 <SEP> CII20000iI3 <SEP> -OÌ7 (n) <SEP> Sdp.167-170 "
<tb> <SEP> 0.4 <SEP> Torr
<tb> <SEP> 111 <SEP> 02115 <SEP> 602II5 <SEP> 01120000113 <SEP> -CH3 <SEP> Sdp. <SEP> 170T0o / 0rr5
<tb> <SEP> 112 <SEP> Cm3 <SEP> 6 <SEP> -CH3 <SEP> 1 <SEP> -CH2 <SEP> -CONHCH3 <SEP> -CH3 <SEP> Smp. 129-1300
<tb> <SEP> 113 <SEP> CH3 <SEP> 6-Cil3 <SEP> -0112-C0NiICH3 <SEP> -C3117 (n) <SEP> Smp. <SEP> 63-650
<tb> <SEP> 114 <SEP> 02115 <SEP> 6-C2H5 <SEP>, <SEP> -CTI2-CONH2 <SEP> -CH3 <SEP> Smp. <SEP> 1380
<tb> <SEP> 115 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-CCOCH3 <SEP> 0H20lI (C1I3) 2 <SEP> Sdp <SEP> 130 <SEP> / 0 <SEP> 01
<tb> <SEP> 116 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-CONHCH3 <SEP> -CH2-CH (CH3) <SEP> 2 <SEP> Smp.

  <SEP> 80-860
<tb> <SEP> 117 <SEP> 02115 <SEP> 6 <SEP> -C2H5 <SEP> -CH <SEP> -CODICT13 <SEP> -CH = CH <SEP> -CH3 <SEP> Smp.107-090
<tb> <SEP> 118 <SEP> 02115 <SEP> 6 <SEP> 11 <SEP> 0H200N1I2 <SEP> 3H7 <SEP> (n) <SEP> Smp. <SEP> 1C3 "
<tb> <SEP> 25
<tb> <SEP> 119 <SEP> C2H5 <SEP> 6 <SEP> -C2H5 <SEP> -CH2-CONHC2H5 <SEP> -0113 <SEP> Snw.

  <SEP> 73.740
<tb> <SEP> 120 <SEP> 02115 <SEP> -C2H5 <SEP> 1 <SEP> -0112-C0NH02H5 <SEP> CqHg (iso) <SEP> Sdp.1520 /
<tb> <SEP> 121 <SEP> CH, <SEP> 6-CH3 <SEP> -CH2-COOCH3 <SEP> 17H35 <SEP> (n) <SEP> O.OlTorr
<tb> <SEP> 122 <SEP> CH3 <SEP> 6-C1 <SEP> -CH2 <SEP> -CONHCH3 <SEP> -C4119 (iso)
<tb> <SEP> 123 <SEP> OCH3 <SEP> H <SEP> -CH-CONH2 <SEP> -CH = CH2
<tb> <SEP> OH3
<tb> <SEP> 124 <SEP> C4119 (t) <SEP> 6-CH3 <SEP> -CH2-CON (CH3) <SEP> 2 <SEP> C5H11 (n)
<tb> <SEP> 125 <SEP> CH3 <SEP> 6 <SEP> -CH3 <SEP> 2 <SEP> -CgH <SEP> 19 <SEP> (<SEP> n)
<tb> <SEP> OH2
<tb> <SEP> 126 <SEP> C1 <SEP> 5-C1 <SEP> -CII-CONH2
<tb> <SEP> 127 <SEP> C1 <SEP> 6 <SEP> -C <SEP> -CH (CH.-COOCH.H2>
<tb> <SEP> 128 <SEP> 0113 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH (CE13) -COOCH3 <SEP> | <SEP> nCllH23 <SEP> 0.05 <SEP> Torr
<tb> <SEP> 6OH3 <SEP> OH (CH3) <SEP> 05 <SEP> Torr
<tb>
The compounds of formula I can in

   the agents according to the invention can be used to broaden the spectrum of action with other suitable pesticidal or plant growth-promoting active ingredients.



   According to the invention, the compounds of the formula I are used together with suitable carriers and / or other additives. Suitable carriers and additives can be solid or liquid and correspond to the substances customary in formulation technology such as. B. natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers.



   The content of active ingredient in commercial products is between 0.1 and 90 / e.



   For administration, the compounds of the formula I can be in the following working-up forms (the
Weight percentages in brackets represent advantageous amounts of active ingredient):
Solid forms of processing: dusts and grit (up to 10%), granulates, coated granulates, impregnation granulates and homogeneous granulates (1 to 80/0);
Liquid processing forms: a) Active ingredient concentrates dispersible in water: spray powder and pastes (25-90% in the commercial pack, 0.01 to
15 / o in ready-to-use solution); Emulsion and solution concentrates (10 to 50% 0.01 to 15 / o in ready-to-use
Solution); b) solutions (0.1 to 20%);
The active ingredients of the formula I of the present invention can be formulated, for example, as follows:
Dust:

  The following substances are used to produce a) 50 / above and b) 20 / own dust: a) 5 parts of active ingredient
95 parts of talc; b) 2 parts of active ingredient
1 part of highly dispersed silica
97 parts of talc.



   The active ingredients are mixed and ground with the carrier substances and can be dusted in this form for use.



   Granules:
The following substances are used to produce a 50 / above granulate:
5 parts of active ingredient 0.25 parts of epichlorohydrin
0.25 part of cetyl polyglycol ether
3.50 parts of polyethylene glycol
91 parts of kaolin (grain size 0.3-0.8 mm).



   The active ingredient is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether is added. The solution obtained in this way is sprayed onto kaolin, and the acetone is then evaporated in vacuo. Such microgranules are advantageously used for combating soil fungi.



  Wettable powder:
To produce vines a) 700 / above b) 400 / above c) and d) 250 / above e) 100 / above wettable powder, the following ingredients are used: a) 70 parts of active ingredient
5 parts of sodium dibutyl naphthyl sulfonate
3 parts of naphthalenesulfonic acids-phenolsulfonic acids
Formaldehyde condensate 3: 2: 1
10 parts of kaolin
12 parts of champagne chalk; b) 40 parts of active ingredient
5 parts of lignin sulfonic acid sodium salt
1 part dibutylnaphthalenesulfonic acid sodium salt
54 parts of silica; c) 25 parts of active ingredient
4.5 parts calcium lignosulfonate
1.9 parts of champagne chalk / hydroxyethyl cellulose
Mixture (1: 1)
1.5 parts of sodium dibutyl naphthalene sulfonate
19.5 parts of silica
19.5 parts of champagne chalk
28.1 parts of kaolin;

   d) 25 parts of active ingredient
2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol
1.7 parts of champagne chalk / hydroxyethyl cellulose
Mixture (1: 1)
8.3 parts of sodium aluminum silicate
16.5 parts of diatomaceous earth
46 parts of kaolin; e) 10 parts of active ingredient
3 parts mixture of the sodium salts of saturated
Fatty alcohol sulfates
5 parts of naphthalenesulfonic acid / formaldehyde condensate
82 parts of kaolin;
The active ingredients are intimately mixed with the additives in suitable mixers and ground on appropriate mills and rollers. The wettable powder obtained has excellent wettability and suspension properties, which can be diluted with water to give suspensions of the desired concentration and especially used for foliar application.



  Emulsifiable concentrates:
The following substances are used to produce a 250 / self-emulsifiable concentrate: 25 parts of active ingredient
2.5 parts of epoxidized vegetable oil and 10 parts of an alkylarylsulfonate / fatty alcohol poly glycol ether mixture
5 parts of dimethylformamide, 57.5 parts of xylene.



   Such concentrates can be diluted with water to produce emulsions of the desired concentration, which are particularly suitable for dressing and foliar application.

 

  Example 1 Action against Phytophthora infestans on tomatoes.



   Ia) Residual preventive effect
Three-week-old tomato plants of the Roter Gnom variety were infected with a zoospore suspension of Phytophthora infestans after they had been sprayed with a broth containing 0.06% active substance (prepared from the active substance worked up into a wettable powder) and the spray coating had dried on. They then stayed for 6 days in a climatic chamber at 18 to 20 and high humidity, which was generated by an artificial spray. After this time, typical leaf spots appeared.



  Their number and size served as an evaluation standard for the tested substance.



  Ib) Curative effect
After three weeks of cultivation, tomato plants of the Red Gnome variety were sprayed with a zoospore suspension of the fungus and incubated in a cabin at 18 to 20 and with saturated atmospheric humidity. Interruption of humidification after 24 hours. After the plants had dried, they were sprayed with a broth which contained the active substance formulated as a wettable powder in a concentration of 0.06%. After the spray coating had dried on, the plants were again placed in the moist cabin for 4 days. The number and size of the typical leaf spots that appeared after this time were used as a benchmark for the effectiveness of the substances tested.



  II) Preventive-systemic effect.



   The active substance, formulated as a wettable powder, was added in a concentration of 0.006% (based on the soil volume) to the soil surface of three-week-old potted tomato plants of the Red Gnome variety. After a three-day waiting period, the underside of the leaves of the plants was sprayed with a zoospore suspension of Phytophthora infestans. They were then kept for 5 days in a spray booth at 18 to 20 and saturated humidity. After this time, typical leaf spots formed, the number and size of which were used to assess the effectiveness of the substances tested.



   In these three experiments, the compounds of the formula I show a strong leaf fungicidal action. With compounds No. 1, 2, 7, 12, 22, 35, 37, 47, 63, 76, 95, 96, 97, 113 and others, the fungal attack is less than 20/0 in comparison with infected but untreated control plants inhibited.



  Example 2 Action against Plasmopara viticola (Bert. Et Curt.) (Berl. Et DeToni) on vines a) Residual preventive action
Vine cuttings of the Chasselas variety were grown in the greenhouse. At the 10-leaf stage, 3 plants were sprayed with a broth (0.06% active ingredient) prepared from the active ingredient formulated as a wettable powder.



  After the spray coating had dried on, the plants on the underside of the leaves were evenly infected with the spore suspension of the fungus. The plants were then kept in a humid chamber for 8 days.



  After this time, the control plants showed clear symptoms of disease. The number and size of the infection sites on the treated plants served as an evaluation standard for the effectiveness of the substances tested.



  b) Curative effect
Vine cuttings of the Chasselas variety were grown in the greenhouse and infected at the 10-leaf stage with a spore suspension of Plasmopara viticola on the underside of the leaves. After staying in the humid cabin for 24 hours, the plants were sprayed with a 0.06% active ingredient broth made from a wettable powder of the active ingredient had been manufactured. The plants were then kept in the humid cabin for 7 days. After this time, the symptoms of the disease appeared on the control plants.



  The number and size of the infection sites on the treated plants served as an evaluation standard for the effectiveness of the substances tested.



   The compounds of the formula I showed strong leaf fungicidal effects in these two experiments. In compounds No. 1, 2, 7, 10, 12, 13, 22, 35, 37, 38, 46, 47, 63, 76, 77 and others, the infestation was inhibited to less than 20%.



  Example 3 Action against Erysiphe graminis on Hordeum vulgare (barley) Residual protective action
Approx. Barley plants 8 cm high were sprayed with a spray mixture prepared from a wettable powder formulation of the active ingredient (0.02% active ingredient). After 48 hours, the treated plants were dusted with conidia of the fungus.



  The infected barley plants were placed in a greenhouse at about 22 ° C. and the fungal attack was assessed after 10 days.



   Compounds No. 32, 48, 53, 54, 55, 66, 69 and others showed in this test a reduction in fungal attack to <20% in comparison with untreated but infected control plants.

 

  Example 4 Inhibition of growth on grasses
On an established outdoor lawn consisting of the grasses Lolium perenne, Poa pratensis and Festuca rubra, plots 3 m2 in size were sprayed with aqueous preparations of an active ingredient of the formula I two days after the first cut in spring. The amount of active ingredient used was the equivalent of 5 kg of AS / per hectare. Untreated plots were left as controls. 6 weeks after application, the average height of the grasses in treated and untreated plots was determined.



  The sward treated with the active ingredients was uniformly compact and had a healthy appearance. In particular, active ingredients of the formula I in which -X-R3 denotes the radical -CH2-CN or -CH2CO-N (R ") (R" ') defined for formula I, showed marked growth inhibition.

 

Claims (1)

PATENT CLAIMS I. Fungicidal agents containing a compound of the formula I as at least one active component EMI13.1 wherein Rl C1-C4-alkyl, Cs-C4 alkoxy, halogen, R2 hydrogen, C1-C3-alkyl, halogen, EMI13.2 or -CN, where R ', R "and R"' are independently hydrogen, methyl or ethyl and R4 is Cl-Cl7-alkyl, C2-C17-alkenyl or C3-C7-cycloalkyl which is optionally substituted by cyano or rhodano . II. Use of an agent according to claim I for combating phytopathogenic fungi. SUBCLAIMS 1. Agent according to claim 1, wherein in formula I R4 is C1-C6 alkyl, C2-C4 alkenyl or C3-C7 cycloalkyl. 2. Agent according to claim 1, wherein the active component is N- (1'-methoxycarbonyl-ethyl) -N-cyclopropylcarbonyl2,6-dimethylaniline. 3. Agent according to claim 1, wherein the active component is N- (1'-methoxycarbonyl-ethyl) -N-vinylcarbonyl-2,6-dimethylaniline.