AU4639089A - Methyl esters of aldimino- or ketimino-oxy-ortho-tolylacrylic acid, manufacturing process and fungicides containing them - Google Patents

Methyl esters of aldimino- or ketimino-oxy-ortho-tolylacrylic acid, manufacturing process and fungicides containing them Download PDF

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Publication number
AU4639089A
AU4639089A AU46390/89A AU4639089A AU4639089A AU 4639089 A AU4639089 A AU 4639089A AU 46390/89 A AU46390/89 A AU 46390/89A AU 4639089 A AU4639089 A AU 4639089A AU 4639089 A AU4639089 A AU 4639089A
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Australia
Prior art keywords
methyl
methoxy
acrylate
tolyl
oxy
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AU46390/89A
Inventor
Hans Peter Isenring
Stephan Trah
Bettina Weiss
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Novartis AG
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Ciba Geigy AG
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Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of AU4639089A publication Critical patent/AU4639089A/en
Abandoned legal-status Critical Current

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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • 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
    • C07D307/10—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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Abstract

Novel compounds of formula (I), where X is an aldimino or ketimino group, process for manufacturing them, fungicides containing these compounds as active substances, and the use of these active substances and fungicides to destroy fungi in agriculture and gardening.

Description

F. HOFFMANN-LA ROCHE AG, Basle/Switzerland RAN 6103/49 PCT/CH 89/00216 Derivatives of Acrylic Acid 5 The present invention relates to aromatic compounds, namely substituted methyl 2-phenyl-3-methoxy acrylates of the general formula 10 C!i0C COOCH.4 15 0 where X represents an aldimino or ketimino group, in particular a group 20 R1
C=N
25 where R 1 and R 2 independently of one another denote hydrogen, C 1
-
1 2 -alkyl, C 1 3- 4 -haloalkyl, C 1
_
4 -alkoxy
C
1 _4-alkyl, C 1
_
4 -alkylthio-Cl_ 4 -alkyl, aryl-C3_ 4 -alkyl, 30 aryloxy-C3 _ 4 -alkyl, arylthio-C3 _ 4 -alkyl, heteroaryl-C3_ 4 alkyl, C 2 -1 2 -alkenyl, aryl-C 2
-
4 -alkenyl, heteroaryl-C 2 -4 alkenyl, C 2 -1 2 -alkynyl, C 3
-
6 -cycloalkyl, aryl, heteroaryl, cyano or one of the groups (a) to (d) 35
COOR
3 (a)
CONR
4
R
5 (b)
COR
6 (c) CR 7
=NOR
8 (d) or R 1 and R 2 together with the carbon atom to which they are attached denote a 4-7-membered ring which optionally - 2 contains an oxygen or sulphur atom and which can contain one or two fused aromatic rings, for example optionally substituted benzene rings, and R 3 , R 4 , R 5 , R 6 , R 7 and R 8 in each case denote 5 hydrogen,Cl_ 4 -alkyl, aryl or heteroaryl. The compounds according to the invention have fungicidal properties and are suitable as fungicidal active substances, in particular for use in agriculture and 10 horticulture. The invention furthermore relates to a process for the manufacture of the compounds according to the invention, to fungicidal compositions which contain such 15 compounds as active substances, and to the use of such compounds and compositions for controlling fungi in agriculture and horticulture. In the above formula I, all the "alkyl", "alkenyl" 20 and "alkynyl" groups, as such or as a component of larger groups, for example heteroarylalkyl, can be straight-chain or branched, depending on the number of carbon atoms they contain. In addition, the alkenyl and alkynyl groups can in each case have more than one double or triple bond. A 25 halogen atom which may be present is fluorine, chlorine, bromine or iodine, fluorine, chlorine and bromine being preferred. A group, -such as, for example, alkyl, as such or as a component of a larger group which in each case has more than one halogen substituent, can have identical or 30 different halogen atoms.- Aryl is taken to mean, in particular, phenyl, naphthyl, phenanthryl or fluorenyl, heteroaryl is taken to mean a heterocyclic group having aromatic character, such as pyrrolyl, pyridyl, furyl, thienyl, isoxazolyl, thiazolyl, imidazolyl, pyrimidinyl or 35 triazolyl, or such a group with a benzene nucleus fused to it, for example quinolinyl, benzofuryl, benzothienyl or dibenzofuryl. This also applies to aryl or heteroaryl as part of a larger group, for example aralkyl or heteroarylalkyl. The aryl and heteroaryl groups can in - 3 each case have one or more substituents, this substituent or these substituents being suitably selected from amongst halogen, C3_ 4 -alkyl, C 1
_
4 -haloalkyl, Cl_ 4 -alkoxy-Cl_ 4 alkyl, aryl-Cl_ 4 -alkyl, heteroaryl-C3_ 4 -alkyl, aryloxy 5 C3_4-alkyl, heteroaryloxy-C1
_
4 -alkyl, C 2
-
4 -alkenyl, aryl-C 2
-
4 -alkenyl, heteroaryl-C2- 4 -alkenyl, C 2 -4-alkynyl,
C
3
-
6 -cycloalkyl, aryl, heteroaryl, C3_ 4 -alkoxy, C3_ 4 -haloalkoxy, aryl-C 1
_
4 -alkoxy, heteroaryl-C3_ 4 -alkoxy,
C
2
-
4 -alkenyloxy, C 2
-
4 -alkynyloxy, aryloxy, heteroaryloxy, 10 C3_ 4 -alkylthio, cyano, nitro, a group NR 9
R
1 O, a group COR 11 and a group COOR 12 (where R 9 , R 10 , R 11 and R 12 in each case denote C3_ 4 -alkyl, aryl or heteroaryl). If the compounds of the formula I have asymmetric 15 carbon atoms, the compounds occur in optically active form. By virtue of the aliphatic and the imino double bond alone, the compounds occur in any case in the [E] or [Z] form. It is also possible that atropisomerism occurs. Formula I is intended to embrace all these possible isomeric forms as 20 well as their mixtures, for example racemic mixtures and any [E/Z] mixtures. A particular group of compounds of the formula I consists of those compounds of the formula I in which X 25 denotes a group RlR 2 C=N-, where R 1 and R 2 independently of one another denote hydrogen, C 1 -1 2 -alkyl, C3_ 4 -haloalkyl, aryl-C3_ 4 -alkyl, heteroaryl-C3_ 4 -alkyl, C 2 -1 2 -alkenyl, aryl-C 2
-
4 -alkenyl, heteroaryl-C 2
-
4 -alkenyl, C 2 -1 2 -alkynyl,
C
3
-
6 -cycloalkyl, aryl, heteroaryl, cyano or one of the 30 abovementioned groups (a) to (d), or R 1 and R 2 together with the carbon atom to which they are attached denote a ring as defined in greater detail above. In the group RlR 2 C=N-, R 1 and R 2 being independent 35 of one another, R 1 preferably denotes optionally substi tuted phenyl, any substituents which may be present preferably being up to three identical or different halogen atoms (in particular fluorine, chlorine and/or bromine),
C
1
.
4 -alkyl groups (in particular methyl), Cl_ 4 -haloalkyl - 4 groups (in particular trifluoromethyl) and/or C 1
_
4 -halo alkoxy groups (in particular trifluoromethoxy), and R 2 preferably denotes hydrogen, C 1
-
12 -alkyl (in particular methyl or ethyl), C1-4-haloalkyl (in particular 5 trifluoromethyl) or C 3
-
6 -cycloalkyl (in particular cyclo propyl).
R
1 likewise preferably denotes heteroaryl, in particular furyl which is optionally substituted with up to 10 two methyl groups, thienyl which is optionally substituted with chlorine or methyl, or benzofuryl, and R 2 likewise preferably denotes methyl. In general, the [E] forms of the compounds of the 15 formula I are preferred to the [Z] forms. Particularly preferred individual compounds of the formula I are: 20 methyl 3-methoxy-2-[a-{[(a-methyl-benzyl)imino] oxy)-o-tolylI-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3,5-di-tri fluoromethyl-benzyl)imino oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-2-fluoro-5 25 methyl-benzyl)imino]oxy}-o-tolyl]-acrylate, methyl 1-[a-{[(l-[ 2 -benzofuryl]-ethyl)imino]oxy) o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[( 3 -nitrobenzyl)imino]oxy} o-tolyl]-acrylate, 30 methyl 3-methoxy-2-[a-{[(a-trifluoromethyl benzyl)iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-4-fluorobenzyl) imino oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(l-[2-thienyl]-ethyl) 35 iminoloxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-4-chlorobenzyl) imino oxy}-o-tolyl]-acrylate, methyl 2-[a-{[(a-cyclopropyl-benzyl)iminooxy}-o tolyl]-3-methoxy-acrylate, - 5 methyl 2-[a-{[(1-[5-chloro-2-thienyl]-ethyl) imino oxy}-o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-trifluoro methyl-benzyl)imino oxy}-o-tolyl]-acrylate, 5 methyl 3-methoxy-2-[a-{[(a-methyl-3-bromobenzyl) imino]oxy}-o-tolyl]-acrylate, methyl 2-[a-{[(1-[3,5-dimethyl-2-furyl]-ethyl) iminoloxy}-o-tolyll-3-methoxy-acrylate, methyl 2-[a-{[(1-[2,5-dimethyl-3-thienyl]-ethyl) 10 imino]oxy)-o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-chlorobenzyl) iminoloxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-methylbenzyl) imino]oxy)-o-tolyl]-acrylate, 15 methyl 3-methoxy-2-[a-{[(a-methyl-4-methylbenzyl) imino]oxy}-o-tolyl]-acrylate, methyl 2-[a-{[(3-fluorobenzyl)imino]oxy)-o-tolyl] 3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-4-trifluoro 20 methyl-benzyl)imino]oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-fluoro-5-tri fluoromethyl-benzyl)imino1oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-fluorobenzyl) imino]oxy}-o-tolyl]-acrylate, 25 methyl 3-methoxy-2-[a-{[(a-methyl-3-trifluoro methoxy-benzyl)imino]oxy}-o-tolyl]-acrylate and methyl 2-[a-{[(a-ethyl-3-trifluoromethyl-benzyl) imino]oxy}-o-tolyl]-3-methoxy-acrylate. 30 Other preferred individual compounds of the formula I are: methyl 2-[a-{[(1-[2-furyl]-ethyl)imino]oxy}-o tolyl]-3-methoxy-acrylate, 35 methyl 3-methoxy-2-[a-{[(1-[2-naphthyl]-ethyl) imino oxy}-o-tolyl]-acrylate, methyl 2-[a-{[(4-chlorobenzyl)iminoloxy}-o-tolyl] 3-methoxy-acrylate, methyl 2-[a-{[(2,4-dichlorobenzyl)imino]oxy}-o- - 6 tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-4-nitrobenzyl) imino oxy}-o-tolyl]-acrylate, methyl 2-[a-{(benzylimino)oxy}-o-tolyll-3-methoxy 5 acrylate, methyl 3-methoxy-2-[a-([(2-pyridylmethyl)imino] oxy}-o-tolyl]-acrylate, methyl 2-[a-{[(a-ethyl-benzyl)imino]oxy}-o-tolyl] 3-methoxy-acrylate, 10 methyl 2-[a-{[(a-ethyl-4-chlorobenzyl)imino]oxy} o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-[n-propyl]-benzyl) imino oxy}-o-tolyl]-acrylate, methyl 2-[a-{[(1-[benzoyl]-ethyl)imino]oxy}-o 15 tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl- (-phenyl-allyl) iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-4-phenoxy benzyl)iminoIoxy}-o-tolyl]-acrylate, 20 methyl 2-[a-{[(a-cyclopropyl-4-chlorobenzyl) iminoloxy}-o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-([(1-[2-pyridyl]-ethyl) iminoIoxy)-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(1-[3-pyridyll-ethyl) 25 imino]oxy)-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(1-[5-methyl-2-furyl] ethyl)iminoloxy}-o-tolyl]-acrylate, methyl 2-[a-{[(dicyclopropylmethyl)iminoloxy}-o tolyl]-3-methoxy-acrylate, 30 methyl 3-methoxy-2-[a-{[(2-naphthylmethyl)imino] oxy}-o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-nitrobenzyl) iminoIoxy}-o-tolyl]-acrylate, methyl 2-[a-{[(1-[2,4-dimethyl-5-thiazolyl] 35 ethyl)iminoloxy}-o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-4-methoxy benzyl)iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3,4-dichloro benzyl)iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-([(a-methyl-2-fluorobenzyl) imino oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-2,4-dimethyl benzyl)imino oxy}-o-tolyl]-acrylate, 5 methyl 3-methoxy-2-[a-{[(a-methyl-4-ethylbenzyl) imino oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-([(a-methyl-3-ethylbenzyl) imino]oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-([(a-methyl-3,4-dimethyl 10 benzyl)imino]oxy}-o-tolyl]-acrylate, methyl 2 -[a-{[(l-[5-bromo-2-thienyl]-ethyl)imino oxy}-o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(1-[2-naphthyl]-propyl) iminoIoxy}-o-tolyl]-acrylate and 15 methyl 2-[a-([(a-cyclopropyl-2-naphthylmethyl) imino]oxy}-o-tolyll-3-methoxy-acrylate. Other representatives of compounds of the formula I are: 20 methyl 3-methoxy-2-[a-{[(a-methyl-2,3-difluoro benzyl)iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-([(a-methyl-2,4-difluoro benzyl)iminoIoxy}-o-tolyl]-acrylate, 25 methyl 3-methoxy-2-[a-{[(a-methyl-2,5-difluoro benzyl)iminoloxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-([(a-methyl-3,4-difluoro benzyl)iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-([(a-trifluoromethyl- 30 carbonyl-2,3-dichlorobenzyl)iminoloxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-trifluoromethyl-2,3 dichlorobenzoylmethyl)iminoIoxy}-o-tolyll-acrylate, methyl 3-methoxy-2-[a-{[(1-methyl-2-phenoxy propyl)imino]oxy}-o-tolyl]-acrylate, 35 methyl 3-methoxy-2-[a-{[(1-methyl-2-[2-chloro phenoxy]-propyl)iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(1-methyl-2-phenylthio propyl)iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-trifluoromethyl- - 8 carbonyl-2-naphthylmethyl)imino]oxy}-o-tolyl]-acrylate, methyl 2-[a-{[(a-cyclopropylcarbonyl-2-naphthyl methyl)imino oxy}-o-tolyl]-3-methoxy-acrylate, methyl 2-[a-{[(a-isopropyl-2-naphthylmethyl) 5 imino]oxy)-o-tolyl]-3-methoxy-acrylate, methyl 2-[a-{[(a-dimethylaminomethyl-2-naphthyl methyl)imino]oxy}-o-tolyl]-3-methoxy-acrylate and methyl 3-methoxy-2-[a-{[(2,4,4-trimethyl-1-cyclo hexen-6-yl)iminoIoxy}-o-tolyl]-acrylate. 10 The process according to the invention for the manufacture of the compounds according to the invention is characterized in that an oxime X-OH, in particular an oxime of the general formula 15 R1 C=N-OH II R2 20 where R 1 and R 2 have the abovementioned meanings is reacted with a benzyl alcohol derivative of the general formula CH OHC COOCH3 C 25 UC H where U denotes a leaving group. 30 This reaction is a nucleophilic substitution which can be carried out under the reaction conditions customary for such substitutions. The leaving group U in the benzyl alcohol derivative of the formula III is preferably taken 35 to mean chlorine, bromine, iodine, mesyloxy or tosyloxy. The reaction is suitably carried out in an inert organic diluent, such as a cyclic ether, for example tetrahydro furan or dioxan, acetone, dimethyl formamide or dimethyl sulphoxide, in the presence of a base, such as sodium - 9 hydride, sodium carbonate or potassium carbonate, of a tertiary amine, for example a trialkyl amine, in particular diazabicyclononane or diazabicycloundecane, or silver oxide, at temperatures between -20 0 C and 80 0 C, preferably 5 in the temperature range from 0*C to 20 0 C. Alternatively, the reaction can be carried out under phase transfer catalysis at room temperature in an organic solvent, such as, for example, methylene chloride, 10 in the presence of an aqueous basic solution, for example sodium hydroxide solution, and of a phase transfer catalyst, such as, for example, tetrabutylammonium bisulphate. 15 The resulting compounds of the formula I can be isolated and purified by methods known per se. Any mixtures of isomers which are obtained, for example mixtures of E/Z isomers, can be separated to give the pure isomers likewise by methods known per se, for example by 20 chromatography or fractional crystallisation. The oximes X-OH which are used as starting materials in the process according to the invention, for example those of the formula II, are either known or they 25 can be produced by methods known per se, for example by reacting the corresponding carbonyl compound R 1
R
2 C=O with hydroxylamine hydrochloride in the presence of a base, for example sodium hydroxide, potassium hydroxide or pyridine. For other methods, see Houben-Weyl, "Methoden der 30 Organischen Chemie" ["Methods of Organic Chemistry"], volume X/4, pages 3-308 (1968) ("Herstellung und Umwandlung von Oximen" ["Preparation and Conversion of Oximes"]). Likewise, the starting materials of the formula 35 III can be produced in a manner known per se, for example as described in European Patent Publication No. 203,606 (BASF) and in the references quoted therein.
- 10 The compounds according to the invention have fungicidal activity and can accordingly be used for controlling fungi in agriculture, horticulture and wood processing. They are particularly suitable for inhibiting 5 the growth of, or destroying, phytopathogenic fungi on parts of plants, for example leaves, stems, roots, tubers, fruits or flowers, and on seeds, and for inhibiting the growth of, or destroying, pathogenic fungi which occur in the soil. It is furthermore possible to control wood 10 destroying and wood-discolouring fungi with the compounds according to the invention. For example, the compounds according to the invention are active in the control of fungi of the classes of the Deuteromycetes, Ascomycetes, Basidiomycetes and Phycomycetes. 15 The compounds according to the invention are particularly suitable for controlling the following pathogens: 20 Powdery mildews (for example Erysiphe graminis, Erysiphe cichoracearum, Podosphaera leucotricha, Uncinula necator, Sphaerotheca spp.) Rusts (for example Puccinia tritici, Puccinia 25 recondita, Puccinia hordei, Puccinia coronata, Puccinia striiformis, Puccinia arachidis, Hemileia vastatrix, Uromyces fabae) Scabs (for example Venturia inaequalis) 30 Cercospora spp. (for example Cercospora arachidicola, Cercospora beticola) Mycosphaerella spp. (for example Mycosphaerella 35 fijiensis) Alternaria spp. (for example Alternaria brassicae, Alternaria mali) - 11 Septoria spp. (for example Septoria nodorum) Helminthosporium spp. (for example Helminthosporium teres, Helminthosporium oryzae) 5 Plasmopara spp. (for example Plasmopara viticola) Pseudoperonospora spp. (for example Pseudoperonospora cubensis) 10 Phytophtora spp. (for example Phytophtora infestans) Pseudocercosporella spp. (for example 15 Pseudocercosporella herpotrichoides) Pyricularia spp. (for example Pyricularia oryzae) Furthermore, the compounds are active against, for 20 example, fungi of the genera Tilletia, Ustilago, Rhizoctonia, Verticillium, Fusarium, Pythium, Gaeumannomyces, Sclerotinia, Monilia, Botrytis, Peronospora, Bremia, Gloeosporium, Cercosporidium, Penicillium, Ceratocystis, Rhynchosporium, Pyrenophora, 25 Diaporthe, Ramularia and Leptosphaeria. Certain representatives of the compounds according to the invention have an additional action against wood-destroying fungi, such as, for example, those of the genera Coniophora, Gloeophyllum, Poria, Merulius, Trametes, Aureobasidium, 30 Sclerophoma and Trichoderma. The compounds according to the invention are distinguished by a prophylactic and curative action. 35 Under greenhouse conditions, the compounds according to the invention are active against phytopathogenic fungi at concentrations of as little as 0.5 mg to 500 mg of active substance per litre of spray liquor. In the field, it is advantageous to apply dosages of 20 g - 12 to 1 kg of active substance of the formula I per hectare per treatment. To control seed-borne fungi or fungi which occur in the soil by seed-dressing, it is advantageous to use dosages of 0.01 g to 1.0 g of active substance of the 5 formula I per kg of seed. The compounds according to the invention can be formulated to give a range of compositions, for example solutions, suspensions, emulsions, emulsifiable 10 concentrates and preparations in the form of powders. The fungicidal compositions according to the invention are characterized in that they contain an effective amount of at least one compound of the general formula I, as defined above, in addition to formulation adjuvants. It is 15 expedient for the compositons to contain at least one of the following formulation adjuvants: Solid carriers; solvents or dispersion media; tensides (wetting agents and emulsifiers); dispersing 20 agents (without tenside action); and stabilizers. Solid carriers which are suitable are, mainly, natural mineral substances, such as kaolin, clays, kieselguhr, talc, bentonite, chalk, for example whiting, 25 magnesium carbonate, limestone, quartz, dolomite, attapulgite, montmorillonite and diatomaceous earth; synthetic mineral substances, such as highly-dispersed silica, alumina and silicates; organic substances, such as cellulose, starch, urea and synthetic resins; and 30 fertilizers, such as phosphates and nitrates, it being possible for such carriers to be present, for example, as granules or powders. Suitable solvents or dispersion media are, mainly, 35 aromatic substances, such as toluene, xylenes, benzene and alkylnaphthalines; chlorinated aromatic substances and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes and methylene chloride; aliphatic hydrocarbons, such as cyclohexane, and paraffins, for - 13 example mineral oil fractions; alcohols, such as butanol and glycol, as well as their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; and strongly polar solvents or 5 dispersion media, such as dimethylformamide,
N
methylpyrrolidone and dimethyl sulphoxide, these solvents or dispersion media preferably having flashpoints of at least 30*C and boiling points of at least 50*C, and water. Suitable among the solvents or dispersion media are also 10 so-called liquefied gaseous extenders or carriers, which are those products which are gaseous at room temperature and under atmospheric pressure. Examples of such products are, in particular, aerosol propellants, such as halohydrocarbons, for example dichlorodifluoro 15 methane. If water is used as the solvent, it is also possible to use, for example, organic solvents as auxiliary solvents. The tensides (wetting agents and emulsifiers) can 20 be nonionic compounds, such as condensation products of fatty acids, fatty alcohols or aliphatically substituted phenols with ethylene oxide; fatty acid esters and fatty acid ethers of sugars or polyhydric alcohols; the products which are obtained from sugars or polyhydric alcohols by 25 condensation with ethylene oxide; block polymers of ethylene oxide and propylene oxide; or alkyldimethylamine oxides. The tensides can also be anionic compounds- such 30 as soaps; fatty sulphate esters, for example dodecyl sodium sulphate, octadecyl sodium sulphate and cetyl sodium sulphate; alkylsulphonates, arylsulphonates and aliphatic aromatic sulphonates, such as alkylbenzenesulphonates, for example calcium dodecylbenzenesulphonate, and butyl 35 naphthalenesulphonates; and more complex fatty sulphonates, for example the amide condensation product of oleic acid and N-methyltaurine, and the sodium sulphonate of dioctyl succinate.
- 14 Finally, the tensides can be cationic compounds, such as alkyldimethylbenzylammonium chlorides, dialkyl dimethylammonium chlorides, alkyltrimethylammonium chlorides and ethoxylated quaternary ammonium chlorides. 5 Suitable dispersing agents (without surfactant action) are mainly lignin, sodium salts and ammonium salts of lignin sulphonic acid, sodium salts of maleic anhydride/diisobutylene copolymers, sodium salts and 10 ammonium salts of sulphonated polycondensation products of naphthalene and formaldehyde, and sulphite waste liquors. Examples of dispersing agents which are parti cularly suitable as thickeners and anti-settling agents are 15 methylcellulose, carboxymethylcellulose, hydroxyethyl cellulose, polyvinyl alcohol, alginates, caseinates and blood albumin. Examples of suitable stabilizers are acid-binding 20 agents, for example epichlorohydrin, phenyl glycidyl ether and soya epoxides; antioxidants, for example gallic esters and butyl hydroxytoluene; UV absorbers, for example substituted benzophenones, diphenylacrylonitrile acid esters and cinnamic esters; and deactivators, for example 25 salts of ethylenediamine tetraacetic acid, and polyglycols. In addition to the active substances of the formula I, the fungicidal compositions according to the invention can also contain other active substances, .for 30 example further fungicidal agents, insecticidal and acaricidal agents, bactericides, plant growth regulators and fertilizers. Such combination compositions are suitable for broadening the spectrum of activity or for specifically influencing plant growth. 35 In general, the fungicidal compositions according to the invention contain, depending on their type, between 0.0001 and 85 percent by weight of compound according to the invention, or compounds according to the invention, as - 15 active substance(s). They can be in a form which is suitable for storage and transport. The concentration of active substance in such forms, for example emulsifiable concentrates, is usually in the higher range of the above 5 concentration interval. These forms can then be diluted with the same or different formulation adjuvants down to concentrations of active substance which are suitable for use in practice, and such concentrations are usually in the lower range of the above concentration interval. In 10 general, emulsifiable concentrates contain 5 to 85 percent by weight, preferably 25 to 75 percent by weight, of the compound(s) according to the invention. Suitable use forms are, inter alia, ready-to-use solutions, emulsions and suspensions, which are suitable, for example, as spray 15 liquors. Concentrations of between 0.0001 and 20 percent by weight, for example, can be present in such spray liquors. When using the ultra-low-volume method, it is possible to formulate spray liquors in which the concen tration of active substance is preferably from 0.5 to 20 20 percent by weight, while the spray liquors formulated for the low-volume method and the high-volume method preferably have a concentration of active substance of 0.02 to 1.0 percent by weight, or 0.002 to 0.1 percent by weight, respectively. 25 The fungicidal compositions according to the invention can be prepared by a process in which at least one compound according to the invention is mixed with formulation adjuvants. 30 The compositions can be prepared in a known manner, for example by mixing the active substance with solid carriers, by dissolving or suspending the active substance in suitable solvents or dispersion media, if 35 appropriate with the use of tensides as wetting agents or emulsifiers, or of dispersing agents, or by diluting already prepared emulsifiable concentrates with solvents or dispersion media, etc.
- 16 In the case of compositions in the form of powders, the active substance can be mixed with a solid carrier, for example by grinding the active substance together with the carrier; or the solid carrier can be 5 impregnated with a solution or suspension of the active substance, and the solvent or dispersion media can then be removed by evaporating, heating or by filtering off with suction, under reduced pressure. By adding tensides or dispersing agents, such compositions in the form of powders 10 can be rendered readily wettable with water, so that they can be converted into aqueous suspensions which are suitable, for example, as sprays. The compounds according to the invention can also 15 be mixed with a tenside and a solid carrier to form a wettable powder which is dispersible in water, or they can be mixed with a solid, pre-granulated carrier to form a product in the form of granules. 20 If desired, a compound according to the invention can be dissolved in a water-immiscible solvent, such as, for example, an alicyclic ketone, and this solvent suitably contains a dissolved emulsifier, so that the solution is self-emulsifying on addition to water. Alternatively, the 25 active substance can be mixed with an emulsifier, and the mixture can then be diluted with water to the desired concentration. In addition, the active substance can be dissolved in a solvent, and the solution can then be mixed with an emulsifier. Such a mixture can likewise be diluted 30 with water to the desired concentration. In this manner, emulsifiable concentrates or ready-to-use emulsions are obtained. The compositions according to the invention can be 35 applied by the application methods customary in plant protection or agriculture. The process according to the invention for controlling fungi is characterized in that the material to be protected, for example plants, parts of plants or seeds, is treated with an effective amount of a - 17 compound according to the invention or a composition according to the invention. The examples which follow illustrate the 5 invention. T Manufacture of the active substances of the formula I: Example 1 10 2.0 g (7.0 mmol) of methyl 2-(a-bromo-o-tolyl)-3 methoxyacrylate and 0.95 g (7.0 mmol) of acetophenone oxime are added at 0*C to 0.19 g (7.7 mmol) of sodium hydride in 20 ml of dimethylformamide. After the reaction mixture has 15 been stirred for 10 minutes, saturated sodium bicarbonate solution is added, and the mixture is extracted three times using ethyl acetate. The organic phases are dried over anhydrous sodium sulphate. After the solvent has been distilled off, the oil which remains is purified by 20 chromatography on silica gel using diethyl ether/n-hexane (1:1) as the eluent. In this manner, methyl [E] -3 -methoxy-2-[a-{[(a-methylbenzyl)iminoloxy}-o-tolyl] acrylate is obtained as a yellow oil. 25 Example 2 3.67 g (13.2 mmol) of methyl 2-(a-bromo-o-tolyl) 3-methoxy-acrylate and 3.0 g (13.2 mmol) of 4-phenoxyaceto phenone oxime in 13 ml of methylene chloride are stirred 30 vigorously for 10 minutes at room temperature with 13 ml of 2.2N sodium hydroxide solution and 5.7 g of tetrabutyl ammonium bisulphate. Identical amounts of methylene chloride, 2.2N sodium hydroxide solution and tetrabutyl ammonium bisulphate are then added, and stirring is 35 continued for 10 minutes. Again, identical amounts of 2.2N sodium hydroxide solution and tetrabutylammonium bisulphate are subsequently added, and, after the mixture has been stirred for a further 10 minutes, saturated sodium bicarbonate solution.
- 18 The mixture is extracted three times with ethyl acetate, and the combined organic phases are washed with saturated sodium chloride solution and dried over anhydrous sodium sulphate. After the solvent has been distilled off, 5 the oil which remains is purified by chromatography on silica gel using n-hexane/diethyl ether (4:1) as the eluent. In this manner, methyl [E]-3-methoxy-2-[a-{[(a 10 methyl-4-phenoxybenzyl)imino]oxy}-o-tolyl]-acrylate is obtained as a yellow oil. Examples 3-244 15 Starting from methyl 2-(a-bromo-o-tolyl)-3 methoxyacrylate and the appropriate oxime of the formula II, the compounds of the formula I listed in the table below are obtained in analogy to the process described in Example 1 ("Method 1") or Example 2 ("Method 2"): 20 SC \C cooCH3 1 C I' 25 C N-0-CH2 30 35 -19 Ex~l , ePhysical. Method ledata 1/2 53 cazba~r& cyano up. 136-137C 1 4 2-furyl methyl up. 77C 5 benzoyl ethoxy- Oil1 10 carbonyl 6 3,5-di(tri- mthyl up. 112-1130C1 fluoralethyl) ph~enyl, 7 2-f luoro-5- Oil1 15 methyl-pihflyl 8 2-benzofuranyl Oil1 9 4-chlorcphenfl hyrge p. 119-1210C1 10 2,4-dichiozO- up. 111-1120C1 phnylOi 20 11 3-nitropheflylol1 12 2-quirolinyl up. 114-1150C1 13 5-iiethyl-3- methyl oil methylthio-4 isoxazolyl 25 14 lpenl trifluoro- Oil1 methyl, 15 4-f luoropheflyl methyl oil1 16 4-nitrophenyl up. 145-1460C1 17 phenyl hyrgnoil1 30 18 2-pyridyl oil1 19 3-pyridyl oil1 20 2-chiorophl~l up. 97-980C1 21 benzoYl 'Soil1 22 P-phnylethenYl up. 151-1520C1 35 23 2-thienyl methyl up. 60-610C1 24 4-chloroc*lyl u p. 118-1190C1 25 phenyl ethyl oil1 26 4-chlorophenyl of Oil1 27 phenyl n,-propyl oil1 - 20 Tabe (continuation) Exauple R 1 f Physical Yotbod data 1/2 5 28 phenyl cyclo- oil 1 propyl 29 ethaxycarbonyl cyano up. 91-92'C 1 30 benzoyl methyl oil 1 10 31 p-phenylethenyl up. 113-114'C 1 32 a, a,aC-trifluo0- hydrogen up. 127-128'C 1 p-tolyl 33 2-pyridyl methyl up. 65-67'C 1 34 3-pyridyl oil 1 15 35 4-pyridyl up. 101-103'C 1 36 5-methyl-2-furyl oil 1 37 5-chloro-2- isomer 1: 1 thienyl up. 91-92*C isomer 2 : oil 20 38 2,4-dimethyl-5- " oil 1 thiazolyl 39 o-tolyl oil 1 40 p-anisyl up. 89-90'C 1 41 4-bipheriylyl up. 117-118'C 1 25 42 cyclopropyl cyclopropyl oil 1 43 p-(2-furyl)- methyl oil 1 ethenyl 44 p-(3,4,5-tri- oil 1 methaxy-phenyl) 30 ethenyl 45 4-(4-chloro-3- " oil 1 nitropheniyl) -3 mthyl-1, 3-buta dienyl 35 46 3,4-dichlorophenyl hydrogen up. 95-96*C 1 47 2-naphthyl oil 1 48 2-thiazolyl oil 1 49 a,a,a-trifluoro- methyl up. 55-56*C 1 m-tolyl -21 kxa,1 Physical Method' data 1/2 5 50 3-brcurpheny1 methyl up. 73-74 0 C 1 51 2-chlampbeny1 Oil 1 52 3-nitrcpbny1 Oil 1 53 6-chloro-2- methoxy- uip. 129-130*C 1 10 dubenzfuryl cazfionyl 54 pleny1 phenyl Oil 1 55 5-chloro-3- me~thyl rip. 112-1130C 1 methyl-2-benzo thienyl 15 56 3-chiorophenyl Oil 1 57 3,4-dichioropheflyl rip. 82-83*C 1 58 2,4-dichloropheflyl isomier 1: oil 1 isomer 2: oil 59 2-naphthyl oil 1 20 60 ca-rit1XmX-imli1D- hydrogen oil 1 2, 4-dichlorobenzyl 61 phkenyl n-butyl, Oil 1 62 215-diumthyl-3- me~thyl rip. 68-69-C 2 thienyl 25 63 phenyl isopropyl oil 1 64 pbenyl cyclobexyl oil 1 65 2-(p-tert.butyl- hydrogen oil 1 ethenyl 30 66 2,4-dichlorobenzyl 3-pyridyl oil 1 67 2,4-dichioro- 3-pyridyl- oil 1 pbenyl methyl 68 3-methyl-2- me~thyl rip. 85-860C 1 benzothienyl 35 69 3,5-divathyl-2- toip. 96-970C 1 furyl 70 1-naphthyl hydrogen Oil 1 71 fi-(4-methoxy- pip. 83-87*C 1 pbenyl) -ethenyl -22 Exauple
R
1 f Physical Method data 1/2 72 m-tolyl hydrogen Oil 1 73 2-fluarcphenyl up. 83-84 OC 1 74 3..fluoroplhflYl up. 82-830C 1 75 4-fluorOPh~erYl isome~r 1: 1 10 up. 92-930C isomer 2: oil 76 6-iiethoxy-2- Hoil 1 naph~thyl 77 3-chlorophenYl Oil 1 15 78 3-bxomOpheflYl Oil 1 79 4-brcmDp*enyl rap. 142-1430C 1 80 3-IIethyl-2- oil 1 naphthyl 81 2,3-difuaEoPkhflYl oil 1 20 82 p-.tolyl up. 93-94*C 1 83 2-thienyl Oil 1 84 2,5-dif lurmphfYl Oil 1 85 2-fluoro-6-chlarO- up. 70-730C 1 phenyl 25 86 3-pherKocy-p*hefYl Oil1 87 4-ethyipheflyl oil1 88 3-thienyl isomer 1:1 urp. 125-1260C isomrer 2: oil1 30 89 p-(2-qyixKlirryl)- Oil1 ethenyl 90 fi-(3-tkiienl1)- Oil1 ethenyl 91 a Ia I -trifluoro- oil1 35 m-tolyl 92 p- (N-imethyl-2- oil1 pyrrolyl) -ethenyl 93 4-bnxappheryl methyl up. 123-124"C1 -23 ale(continuation) Exaumle
R
1 12Physical Mthod data 1/2 94 2,5-dichioro- methyl i scxm2r 1: 1 phenyl up. 92-93*C I iscmer 2: oil 95 4-ethyJ4*hfly1 Oil 2 10 96 3-ethyiphefll Oil 2 97 3,4-dimTthyl- raup. 88-890C 2 pbenyl 98 2.4-dimethyl- Oil 2 #I~enyl 15 99 2-fluorcphelyl 73-740C 1 100 m-tolyl np. 750C 2 101 p-tolyl 77-780C 2 102 6-athyl-2- HOil 2 nAphthyl 20 103 5-.lrco-2-thieflyl iscmer 1: 1 up. 980C isomer 2: oil 104 2-tkhienyl tert.butyl oil 1 105 1-n-aphthyl methyl up. 118.5-1210C 1 25 106 2-naphthyl cyclcpropyl oil 1 107 2-naphthyl ethyl oil 1 108 4-difluoro- methyl up. 102-1030C 1 nethw~xphenyl 109 4-chlorophenl1 nepentyl oil1 30 110 2-naphthyl n-prclpyl oil1 111 3 , 5-di (trifluoro- ethyl iscmer 1: oil1 1 methyl ) -phenryl iscxmr 2: oil 112 5,6,7,8-tetra- methyl up. 97-980C 2 hydro-2-naphthyl 35 113 a,,cz-trifluoro- up. 123-124-C 1 P-tolyl 114 3-phenanthryl Noil 2 115 2-f luorenyl oil 2 116 isopropyli Oil 2 - 24 Table continuationn) Exanpie IfPhysical Mathod data 1/2 5 117 4-chlorophenyl n-propyl oil 1 118 4-chlorophenyl cyclopropyl oil 1 119 3-mthIoxyphenyl methyl up. 86-87'C 1 120 3-chlorophenyl ethyl oil 1 10 121 4-fluorophenyl isomer 1: oil 1 isomer 2: oil 122 4-bromophenyl "Mp. 108 0 C 1 123 4-tert.butyl- methyl up. 105-106'C 2 phenyl 124 3-thienyl "p. 87-88*C 1 15 125 cyclopropyl oil 2 126 2-quinolinyl- oil 2 nethyl 127 3-fluoro-5-tri- " p. 102-103*C 1 fluorcuethyl-phenyl 20 128 3-fluorophenyl oil 1 129 3,5-difluorophenyl oil 1 130 3,5-difluorophenyl ethyl oil 1 131 2-fluorophenyl isomer 1: oil 1 isaner 2: oil 25 132 3,4-dimethoxy- methyl oil 2 phenyl 133 p-tolyl ethyl oil 2 134 2,5-dinethyl-3- methyl oil 2 furyl 30 135 phenyl methylthio- isomer 1: oil 1 methyl isomer 2: oil 136 2-thiazolinyl methylthio np. 81-83'C 1 137 benzyl methyl oil 2 138 3-trifluoro-" oil 1 35 methoxy-phenyl 139 3-fluoro-5-tri- ethyl isaer 1: oil 1 fluoranethyl- isamer 2: oil phenyl.
- 25 Table (continuation). Example 112 Physical Method data 1/2 5 140 3,4,5-trimethoXy- methyl oil 2 phenyl 141 2-nitrophenyl oil 1 142 cyclohexyl oil 2 10 143 phenylthicmethyl iscmer 1: oil 2 isomer 2: oil 144 4-chlorophenyl trifluoro- oil 1 methyl 145 2-thienyl cyclopropyl oil 1 15 146 3,4-dimethoxy- methyl oil 1 benzyl 147 aaa-trifluoro- trifluoro- oil 1 m-tolyl methyl 148 a , aa-trifluoro- ethyl oil 1 20 m-tolyl 149 3, 5-dichloro- methyl oil 1 phenyl 150 p-(2-naphthyl)- trifluoro- oil 1 ethenyl methyl 25 151 2-naphthyl oil 1 152 phenyl methoxy- isamer 1: oil 1 methyl isomer 2: oil 153 pheroxymethyl methyl oil 1 154 methyl oil 2 30 155 a,a,a-trifluoro- n-propyl oil 1 m-tolyl 156 ac,aa-trifluoro- methoxy- isomer 1: oil 1 m-tolyl methyl isomer 2: oil 157 2-pyridyl n-propyl oil 1 35 158 aa,a-trifluoro- cyclopropyl oil 1 m-tolyl 159 2-pyridyl " oil 1 160 2-pyridyl methxy- oil 1 methyl -26 Tbe(continuation) Exanpie e Physical Metho~d data 1/2 5 161 2-chlowo-5-tri- izathYl i sazar 1: oil 1 flIuImmethyl iscmer 2: oil 162 2-mothyltbio-5- "iscmer 1: oil 1 10 trifluarczzethyl- iscmer 2: oil phenyl 163 4-chlorco-3-tri- '9Oil 1 f Iuiorcinethyl-benzyl 164 4-methaxybenzyl '9Oil 1 15 165 3-pyridyl ethyl Oil 1 166 arcz-trifluoro- isopr:pY]. Oil 1 m-tolyl 167 Ct C9. -trifluoro- izathyl Oil 1 0-tolyl 20 168 cz,ctr-trifuoro- Ct AC T-oil 1 m-tolyl trifluoro m-tolyl, 169 4-ethw~xphenyl isthl m.p. 79-800C 2 170 N-rathyl-2- '9Oil 1 25 pyrrOlyl 171 10,l1-dihydxD-5H- '9Oil 1 dibenzo[b.f ]aze pin-2-yl 172 3-chloro-4-fluoro- '9m.p. 850C 1 30 penyl 173 2,3-dichlorophenyl '9isazar 1: oil 1 isomer 2: oil 174 p-tolyl trifluoro.- oil 1 mthyl 35 175 4-phenylthIjo- methyl Oil 2 176 4-(2,4-dichloro- '9oil 2 phenoxy) -phenyl 177 4- (4-niLtrophmxxxy) oil 2 40 phenyl -27 Exanpiee Physical Mto data 112 178 4-(4-a~tbOXY - ilethyl Oil 2 phrjiy) -phenyl 179 3,4-rrethylene- Oil 2 10 180 7-benzodioaflYl Oil 2 181 2 ,5-dichloV0-3- isomer 1: oil 1 thienyl isomier 2: oil 182 2-thienyl ethyl isczIr 1: oil 1 isomer 2: oil 15 183 2-chlrophexX~y- n~thYl oil 1 netIyl 184 o-tolyl metboxy- isomer 1: 1 carbonyl m.p. 101-1030C isomer 2: 20 m.p. 85-86*C 185 3-bxwnmbeny1 ethyl Oil 1 186 3-f luoro-5-tri- cyclopzcipyl oil 1 fluaoz1thy1-p211l 187 2,3,4-trichoro- irathyl m.p. 96-970C 1 25 phenyl 188 4-chlaro-3-iI8thYl- m.p. 88*C 1 phkenyl 189 p-tolyl n-propyl Oil 1 190 5-iiathy1-2- methyl, iscumer 1: oil 1 30 thienyl isomer 2: oil 191 2-thieriyl ri-propyl i samer 1: oil 1 isomr 2: oil 192 4-phenoxy-pheflYl cycloprOPYl Oil 2 193 3-bzxmwpheny1 Oil 1 35 194 3-chiorciphenyl oil 1 195 3-f luorophernyl oil 1 196 2-thiazolyl isomier 1: oil 1 isomer 2: m.p. 71-72*C - 28 Table (contirmation) Example R Physical MAthad data 1/2 5 197 3-br=cuphenyl n-propyl oil 1 198 3-chlorphenyl oil 1 199 4-fluneo-3-tri- " oil 1 fluraiethyl-phenyl 10 200 3-fluorophenyl oil 1 201 4-phenoxy-phenyl oil 2 202 3-fluoro-5-tri- oil 1 fluaromethyl-phenyl 203 2-thiazolyl oil 1 15 204 3-brmophenyl trifluoro- oil 1 methyl 205 3-chlorophenyl oil 1 206 2-thiazolyl m.p. 97-98"C 1 207 4-phenoxy-phenyl " oil 1 20 208 2-pyridyl oil 1 209 3-brmophenyl isopropyl oil 2 210 3-chlarophenyl " oil 2 211 2-pyridyl" isar 1: oil 1 isomer 2: oil 25 212 4-phenoxy-phenyl oil 2 213 3-brcmophenyl methoxy- isomer 1: oil 1 methyl ismer 2: oil 214 4-fluaro-3-tri- " iscmer 1: oil 1 fluormethyl- ismer 2: oil 30 phenyl 215 4-fluoro-3-tri- cyclopropyl oil 1 fluarmethyl phenyl 216 2-brcmophenyl methyl oil 1 35 217 4-fluorophenyl cyclopropyl oil 1 218 4-(n-propyl)- mthyl oil 2 phenyl 219 4-methoxy-3-nitro- m.p. 131-132"C 1 phenyl - 29 Table (contination) Exa"ple fe 11 Physical Method data 1/2 5 220 2,3-dihydro-5- methyl oil 2 benzo[b]furyl 221 2-methaxyphenyl " oil 1 222 2,4-dimthoxy- oil 2 10 phenyl 223 4-fluaro-3-tri- isopropyl oil 1 fluoranethyl phenyl 224 3-chlorophenyl methoxy- isauer 1: oil 1 15 methyl isomer 2: oil 225 3-iodophenyl methyl m.p. 103'C 1 226 4-iodophenyl m.p. 124'C 1 227 2-naphthyl methoxy- oil 1 methyl 20 228 2-(4-methoxy- methyl oil 1 phenyl) -ethyl 229 1,4,8-trimethyl- oil 1 xna-1, 3, 7-trienyl 230 1-methyl-2-(3,4- " oil 1 25 methylenedixy phenyl) -ethyl 231 (4-fluorcphenyl)- hydrogen oil 2 carbamoyl - 30 Exirnple Physical Method C data 1/2 5 232 oil 1 C O 233 oil 1 234 oil 1 235 oil 1 10 236 oil 1 C1 237 oil 1 0 C 238 C1oil1 C1 0'.' ~ 31 ~ Example R Physical Method f C data 1/2 239 Oil1 240 oil 1 S C SCH3 241 oil
C"
3 242 oil 10 243 C1 oil S C CH 3 244 cl Oil 1 0C' 3 0 _ CH3 - 32 II. Formulation examples Example 245 5 An emulsifiable concentrate has the following composition: q/litre 10 Active substance (compound according to the invention) 100 Nonylphenol (10)ethoxylate (nonionic emulsifier) 50 Calcium dodecylbenzenesulphonate (anionic emulsifier) 25 N-methyl-2-pyrrolidone (solubilizer) 200 Mixture of alkylbenzenes (solvent) to 1 1 15 The active substance and the emulsifiers are dissolved in the solvent and the solubilizer. A ready to-use spray liquor of any desired concentration can be prepared by emulsifying this concentrate in water. 20 25 30 35 - 33 Example 246 A wettable powder has the following composition: 5 Percent by weight Active substance (compound according to the invention) 25.0 Silica (hydratised; carrier) 20.0 10 Sodium lauryl sulphate (wetting agent) 2.0 Sodium lignosulphonate (dispersing agent) 4.0 Kaolin (carrier) 49.0 15 The components are mixed with each other, and the mixture is ground finely in a suitable mill. Dispersing the mixture in water results in a suspension which is suitable as a ready-to-use spray liquor. 20 25 30 35

Claims (15)

1. Compounds of the general formula 5 3HC COOCH C X---a2 10 where X represents an aldimino or ketimino group.
2. Compounds according to Claim 1, where X represents a 15 group RI R2N 20 where R 1 and R 2 independently of one another denote hydrogen,C 1 - 12 -alkyl, C 1 _ 4 -haloalkyl, Cl_ 4 -alkoxy-Cl_ 4 25 30 35 - 35 alkyl, C 1 _ 4 -alkylthio-C3_ 4 -alkyl, aryl-C3_ 4 -alkyl, aryloxy-C 3_4-alkyl, arylthio-C1.4-alkyl, heteroaryl-C3_4 alkyl, C 2 -1 2 -alkenyl, aryl-C 2 - 4 -alkenyl, heteroaryl-C 2 - 4 alkenyl, C 2 -1 2 -alkynyl, C 3 - 6 -cycloalkyl, aryl, heteroaryl, 5 cyano or one of the groups (a) to (d) COOR 3 (a) CONR 4 R 5 (b) COR 6 (c) CR 7 =NOR 8 (d) or R 1 and R 2 together with the carbon atom to which they are attached denote a 4-7-membered ring which optionally 10 contains an oxygen or sulphur atom and which can contain one or two fused aromatic rings, and R 3 , R 4 , R~ 5 , R 6 , R 7 and R 8 in each case denote hydrogen,C 1 _ 4 -alkyl, aryl or heteroaryl. 15
3. Compounds according to Claim 2, where R 1 and R 2 independently of one another denote hydrogen, C 1 -1 2 -alkyl, C 1 4 -haloalkyl, aryl-C3_ 4 -alkyl, heteroaryl-C3_ 4 -alkyl, C 2 -1 2 -alkenyl, aryl-C 2 - 4 -alkenyl, heteroaryl-C 2 - 4 -alkenyl, 20 C 2 - 12 -alkynyl, C3- 6 -cycloalkyl, aryl, heteroaryl, cyano or one of the groups (a) to (d) indicated in Claim 2, or R1 and R 2 together with the carbon atom to which they are attached denote a ring as defined in greater detail in Claim 2. 25
4. Compounds according to Claim 3, where R 1 denotes optionally substituted phenyl, possible substituents being up to three identical or different halogen atoms, C 1 4 -alkyl groups, C 1 4 -haloalkyl groups and/or 30 C 1 4 -haloalkoxy groups, and R 2 denotes hydrogen, C 1 - 12 -alkyl, C 1 _ 4 -haloalkyl or C3- 6 -cycloalkyl.
5. Compounds according to Claim 3, where R 1 denotes heteroaryl and R 2 denotes methyl. 35
6. Compounds according to any one of Claims 1 to 5 in the [EI-isomeric form.
7. A compound according to Claim 1, selected from - 36 methyl 3-methoxy-2-[a-{[(a-methyl-benzyl)imino] oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3,5-di-tri fluoromethyl-benzyl)imino]oxy}-o-tolyl]-acrylate, 5 methyl 3-methoxy-2-[a-{[(a-methyl-2-fluoro-5 methyl-benzyl)imino]oxy}-o-tolyl]-acrylate, methyl 1-[a-{[(l-[2-benzofuryl]-ethyl)imino]oxy} o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(3-nitrobenzyl)imino]oxy} 10 o-tolyll-acrylate, methyl 3-methoxy-2-[a-{[(a-trifluoromethyl-benzyl) imino oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[a-methyl-4-fluorobenzyl) imino]oxy}-o-tolyl]-acrylate, 15 methyl 3-methoxy-2-[a-{[(1-[2-thienyl]-ethyl) imino]oxy}-o-tolylI-acrylate, methyl 3-methoxy-2-[a-{[a-methyl-4-chlorobenzyl) imino]oxy}-o-tolyl]-acrylate, methyl 2-[a-{[(a-cyclopropyl-benzyl)iminooxy}-o 20 tolyl]-3-methoxy-acrylate, methyl 2-[a-{[(l-[5-chloro-2-thienyl]-ethyl) iminoloxy)-o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-([(a-methyl-3-trifluoro methyl-benzyl)iminoIoxy}-o-tolyl]-acrylate, 25 methyl 3-methoxy-2-[a-{[(a-methyl-3-bromobenzyl) imino1oxy}-o-tolyl]-acrylate, methyl 2-[a-{[(l-[3,5-dimethyl-2-furyl]-ethyl) imino]oxy}-o-tolyl]-3-methoxy-acrylate, methyl 2-[a-{[(l-[ 2 ,5-dimethyl-3-thienyl]-ethyl) 30 imino]oxy}-o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-([(a-methyl-3-chlorobenzyl) iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-methylbenzyl) imino]oxy}-o-tolyl]-acrylate, 35 methyl 3-methoxy-2-[a-{[(a-methyl-4-methylbenzyl) iminoIoxy)-o-tolyl]-acrylate and methyl 2-[a-{[(3-fluorobenzyl)imino]oxy}-o-tolyl] 3-methoxy-acrylate. - 37
8. A compound according to Claim 1, selected from methyl 3-methoxy-2-[a-{ [ (a-methyl-4-trifluoro methyl-benzyl) imino ]oxy }-o-tolyl ]-acrylate, 5 methyl 3-methoxy-2-[a-{[(a-methyl-3-fluoro-5 trifluoromethyl-benzyl)imino]oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-fluorobenzyl) imino]oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-trifluoro 10 methoxy-benzyl)iminoloxy)-o-tolyl]-acrylate and methyl 2-[a-{[(a-ethyl-3-trifluoromethyl-benzyl) imino]oxy}-o-tolyl]-3-methoxy-acrylate.
9. A fungicidal composition, characterized in that it 15 contains an effective amount of at least one compound of the general formula CH3JC* COOCH C 20 Q where X represents an aldimino or ketimino group, 25 as well as formulation adjuvants.
10. A fungicidal composition according to Claim 9, where X of the formula I represents a group 30 C=N R2 where R 1 and R 2 independently of one another denote 35 hydrogen,C3_ 12 -alkyl, C 1 _ 4 -haloalkyl, C 1 _ 4 -alkoxy-C3_ 4 alkyl, C3_ 4 -alkylthio-C3_ 4 -alkyl, aryl-Cl_ 4 -alkyl, aryloxy-C 3_ 4 -alkyl, arylthio-C3_ 4 -alkyl, heteroaryl C 1 4-alkyl, C 2 -1 2 -alkenyl, aryl-C 2 - 4 -alkenyl, heteroaryl- - 38 C 2 - 4 -alkenyl, C 2 -1 2 -alkynyl, C 3 - 6 -cycloalkyl, aryl, heteroaryl, cyano or one of the groups (a) to (d) COOR 3 (a) CONR 4 R 5 (b) 5 COR 6 (c) CR 7 =NOR 8 (d) or R1 and R 2 together with the carbon atom to which they are attached denote a 4-7-membered ring which optionally contains an oxygen or sulphur atom and which can contain 10 one or two fused aromatic rings, and R 3 , R 4 , R 5 , R 6 , R 7 and R 8 in each case denote hydrogen, C 1 4 -alkyl, aryl or heteroaryl. 15
11. A fungicidal composition according to Claim 9, characterized in that it contains an effective amount of at least one compound selected from the group methyl 3-methoxy-2-[a-{[(a-methyl-benzyl)imino] 20 oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3,5-di-tri fluoromethyl-benzyl)imino]oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-2-fluoro-5 methyl-benzyl)imino]oxy}-o-tolyl]-acrylate, 25 methyl 1-[a-{[(l-[ 2 -benzofuryl-ethyl)imino]oxy} o-tolyl]-3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[( 3 -nitrobenzyl)iminoloxy} o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-trifluoromethyl- 30 benzyl)iminoIoxy)-o-tolyl]-acrylate, methyl 3-methoxy-2 -[a-([a-methyl-4-fluorobenzyl) iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(1-[2-thienyll-ethyl) iminoIoxy}-o-tolyl]-acrylate, 35 methyl 3-methoxy-2 -[a-{[a-methyl-4-chlorobenzyl) imino oxy}-o-tolyll-acrylate, methyl 2-[a-{[(a-cyclopropyl-benzyl)iminooxy}-o tolyl]-3-methoxy-acrylate, - 39 methyl 2-[a-{[(l-[5-chloro-2-thienyl]-ethyl) imino]oxy}-o-tolyl]- 3 -methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-trifluoro methyl-benzyl)imino oxy)-o-tolyl]-acrylate, 5 methyl 3-methoxy-2-[a-{[(a-methyl-3-bromobenzyl) imino]oxyl-o-tolyl]-acrylate, methyl 2 -[a-{[(l-[3,5-dimethyl-2-furyl]-ethyl) iminoloxy}-o-tolyl]- 3 -methoxy-acrylate, methyl 2-[a-{[(l-[ 2 ,5-dimethyl-3-thienyl]-ethyl) 10 imino]oxy}-o-tolyl]- 3 -methoxy-acrylate, methyl 3-methoxy-2-[a-([(a-methyl-3-chlorobenzyl) iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-methylbenzyl) imino oxy}-o-tolyl]-acrylate, 15 methyl 3-methoxy-2 -[a-{[(a-methyl-4-methyl benzyl)imino]oxy}-o-tolyl]-acrylate, methyl 2-[a-([( 3 -fluorobenzyl)imino]oxy}-o-tolyl 3-methoxy-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-4-trifluoro 20 methyl-benzyl)imino]oxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-([(a-methyl-3-fluoro-5-tri fluoromethyl-benzyl)iminoIoxy}-o-tolyl]-acrylate, methyl 3-methoxy-2-[a-{[(a-methyl-3-fluorobenzyl) imino]oxy}-o-tolyl]-acrylate, 25 methyl 3-methoxy-2-[a-{[(a-methyl-3-trifluoro methoxy-benzyl)iminoIoxy}-o-tolyl]-acrylate and methyl 2-[a-{[(a-ethyl-3-trifluoromethyl-benzyl) iminoIoxy}-o-tolyl]- 3 -methoxy-acrylate, 30 as well as formulation adjuvants.
12. A process for the manufacture of compounds of the general formula 35 - 40 CHO OlC CoOC'i C .2 5 where X represents an aldimino or ketimino group, characterized in that a compound X-OH where X represents an aldimino or ketimino group is reacted with a benzyl alcohol derivative of the general formula 10 CH Oc\\C H 3 '0 15 where U denotes a leaving group.
13. A process according to Claim 12, characterized in that one of the compounds mentioned in Claims 2 to 8 is 20 produced.
14. A method for controlling fungi in agriculture and horticulture, characterized in that the locus to be protected is treated with an effective amount of a compound 25 according to any one of Claims 1 to 8, or of a composition according to any one of Claims 9 to 11.
15. The use of a compound according to any one of Claims 1 to 8, or of a composition according to any one of 30 Claims 9 to 11, for controlling fungi in agriculture and horticulture. 35
AU46390/89A 1988-12-29 1989-12-12 Methyl esters of aldimino- or ketimino-oxy-ortho-tolylacrylic acid, manufacturing process and fungicides containing them Abandoned AU4639089A (en)

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