GB2226815A - Fungicidal n-acyl cyanamides - Google Patents

Fungicidal n-acyl cyanamides Download PDF

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GB2226815A
GB2226815A GB8900257A GB8900257A GB2226815A GB 2226815 A GB2226815 A GB 2226815A GB 8900257 A GB8900257 A GB 8900257A GB 8900257 A GB8900257 A GB 8900257A GB 2226815 A GB2226815 A GB 2226815A
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optionally substituted
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alkyl
phenyl
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Derek Gilkerson Brough
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Shell Internationale Research Maatschappij BV
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C261/00—Derivatives of cyanic acid
    • C07C261/04—Cyanamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A method of combating fungus at a locus, characterised by treating the locus with a fungicidally effective amount of a compound of general formula <IMAGE> in which R<1> represents an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted phenyl group, an optionally substituted heterocyclic group which is connected by a ring carbon atom to the group -CO-, or a group of formula R<3>-X-, where R<3> represents an optionally substituted phenyl group or an optionally substituted heterocyclic group which is connected by a ring carbon atom to the group X, and X represents an optionally substituted alkylene or alkenylene group, or a group of formula -SO2-; and R<2> represents an optionally substituted cycloalkyl, phenyl or phenalkyl group; including any such compounds in the form of N-oxides and acid addition salts. Certain compounds of formula I and processes for their preparation are novel.

Description

FUNGICIDAL COMPOUNDS This invention relates to the use of certain N-acyl cyanamide compounds as fungicides, to fungicidal compositions containing such compounds, and to certain novel compounds and their preparation.
In Chem. Ztg.,105(6), 194-5, there is disclosed Nmethylcarbonyl, N-phenyl cyanamide. No fungicidal use is suggested for this compound.
In Jp-A-59 75-407 (Kyowa Gas Chem. Ind.) there are disclosed compounds of the general formula
where X represents a hydrogen atom or a hydrogen, C14 or trifluoromethyl group, Y represents a hydrogen atom or a halogen, C14 alkyl or C14 alkoxy group, and n and m represent 1-3. Such compounds are disclosed as having utility as herbicides.
In DE-OLS-2846127 (BASF) there are disclosed, as fungicides, compounds of the general formula Q-C(OR1)(R2)(C(X)Y) where Q represents certain N-connected triazolyl groups, R1 represents an optionally substitute aryl or heteroaryl group, 23 represents a hydrogen atom or an optionaLly substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryi, arylalkyl or heteroaryl group, X represents an oxygen or sulphur atom, and Y represents a group OR5, SR5 or NR6R7 where R5 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl or trialkylsilyl group, R6 represents a hydrogen atom or one of the groups listed for R5, and R7 represents a hydrogen atom, or, independently from R6, one of the groups listed for R5, or a hydroxy group, or an optionally substituted halogen-substituted alkoxy or alkylthio group, a cyano or cyanoalkyl group or a group of formula NR8R9, where R8 and R9 are independently selected from hydrogen atoms and from optionally substituted alkyl or aryl groups; and R6 and R7 may together be, together with the interadjacent nitrogen atom, an optionally substituted ring system, which optionally has one or two double bonds and/or which can additionally be interrupted by one or more heteroatoms from oxygen, nitrogen or sulphur; together with salts and metal complexes.
Of the 296 compounds listed in DE-OLS-2846127, Examples 197-199 are of most relevance to the present invention, in that they are N-acylcyanamide compounds.
Specifically these are of formula
However, no fungicidal efficacy of such compounds is disclosed and, indeed, no analytical data is given to confirm their preparation.
According to the present invention there is provided a method of combating fungus at a locus, characterised by treating the locus with a fungicidally effective amount of a compound of general formula
in which R1 represents an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted phenyl group, an optionally substituted heterocyclic group which is connected by a ring carbon atom to the group -CO-, or a group of formula R3-X-, where R3 represents an optionally substituted phenyl group or an optionally substituted heterocyclic group which is connected by a ring carbon atom to the group X, and X represents an optionally substituted alkylene or alkenylene group, or a group of formula -SO2-; and R2 represents an optionally substituted cycloalkyl, phenyl or phenalkyl group.
Included within the scope of the invention are such compounds in the form of their N-oxides and acid addition salts, where possible.
Unless otherwise state in this specification, an alkyl group may be linear or branched and may suitably contain up to 10, preferably up to 8, carbon atoms, suitable examples being methyl, butyl and hexyl. A cycloalkyl group may suitably contain from 3 to 10, preferably 3 to 8, carbon atoms, a preferred example being a cyclopropyl or cyclohexyl group. An alkylene group may suitably contain 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and will commonly be a methylene group (-CH2-). An alkenylene group may suitably contain 3-6 carbon atoms. A heterocyclic group is suitably monocyclic, and preferably heteroaryl. It may suitably contain 5 or 6 ring atoms, 1-4 ring atoms suitably being hetero (non-carbon) atoms, suitably selected from nitrogen, oxygen and sulphur.When any groups are designated as being optionally substituted, the substituent groups which are optionally present may be any of these customarily employed in the development of pesticidal compounds, and/or the modification of such compounds to influence their structure/activity, persistence, penetration or other property . In relation to alkyl, cycloalkyl, alkylene or alkenylene groups, specific examples of such substituents include halogen, especially fluorine, chlorine and brpmine atoms, and cyano, C14 alkoxy, C14 haloalkoxy, (C1~4 alkyl)carbonyl and phenyl groups. In general, it is preferred, however, that alkyl, cycloalkyl, alkylene or alkenylene moieties in compounds of formula I are unsubstituted.In relation to a phenyl or heterocyclic moiety, optional substituents include halogen, especially fluorine, chlorine and bromine atoms, and nitro, cyano, hydroxyl, C14 alkyl, C14 haloalkyl (expcecially CF3) and C14 alkoxy groups. 1 to 3 substituents may suitably be employed.
More particularly, in relation to the above definitions of R1, an optionally substituted cycloalkyl group is preferably l,l-dimethyl-2-(2,2-dichlorovinyl)cyclopropyl. An optionally substituted phenyl group R1 is preferably a phenyl group optionally substituted by 1-3 moieties independently selected from halogen, especially chlorine, atoms, and C14 alkyl groups. An optionally substituted heterocyclic group R1 may, for example, be an optionally substituted pyridyl, furyl, imidazole, or 2,3-dihydro-1,4-oxathiin group, optionally S-oxidised. Optional substitutents of a heterocyclic group R1 are suitably 1-3 C1-4 alkyl or C24 alkenyl groups, for example methyl and allyl.In relation to R1 as a group of formula R3-X-, R3 as an optionally substituted phenyl group is preferably a phenyl group optionally substituted by 1-3 moieties independently selected from halogen, especially chlorine, atoms, and C14 alkyl and C14 alkoxy groups. R3 as an optionally substituted heterocyclic group is preferably an optionally substituted heteroaryl group, for example, an optionally substituted thienyl group. Optional substituents of such a heterocyclic group R3 are suitably 1-3 C1-4 alkyl groups. X is preferably a C16 alkylene group, linear or branched, optionally substituted by a phenyl or C14 alkoxy group; or a C34 alkenylene group; or a group of formula -SO2-.
Preferably, R1 represents a C18 alkyl group; a phenyl group optionally substituted by 1-2 moieties independently selected from halogen atoms and C14 alkyl groups; an imidazole or furyl group , connected by a ring carbon atom to the group -CO-, and optionally substituted by 1 or 2 C14 alkyl or C24 alkenyl groups; or a 5-(2,3-dihydro-6-methyl-1,4-oxathiin) group, optionally S-oxidised; or a group of formula R3-X- where R3 represents a phenyl group optionally substituted by 1-3 moieties independently selected from halogen, especially chlorine, atoms, and C14 alkyl and C14 alkoxy groups, or R3 represents a thienyl group connected by a ring carbon atom to the group X, and optionally substituted by 1-2 C14 alkyl groups, and X represents a group of formula -CHY- where Y represents a hydrogen atom or a C15 alkyl group, or X represents a C34 alkenylene group.
Most preferably, R1 represents an optionally substituted imidazole group, optionally substituted in accordance with any of the foregoing statements, preferably a group of formula
where Z represents a C14 alkyl group, most preferably i-propyl; or a group of formula R3-X- where R3 represents an optionally substituted, preferably, halophenyl group, preferably chlorophenyl, most preferably 4-chlorophenyl, and X represents a group of formula -CHY- where Y represents a C14 alkyl group, most preferably i-propyl.
R2 as an optionally substituted phenyl group is preferably a phenyl group optionally substituted by 1-3 moieties independently selected from phenoxy groups and halogen, especially chlorine atoms.
R2 as an optionally substituted phenalkyl group is preferably a phenyl group optionally substituted by 1-3 halogen, especially chlorine atoms, bonded to a C14 alkylene group, suitably a group of formula -CHZ- where Z represents C14 alkyl group, or preferably, a hydrogen atom.
R2 as an optionally substituted cycloalkyl group is suitably C38 cycloalkyl, for example cyclohexyl.
Preferably, R2 represents a halophenyl group suitably carrying 1 or 2 halogen, preferably chlorine, substituents, at least one halogen substituent preferably being in the 4-position; or a halobenzyl group having a halophenyl group, suitably carrying 1 or 2 halogen, preferably chlorine substituents, at least one halogen substituent preferably being in the 4position.
Most preferably, R2 represents a 4-chlorophenyl group.
An acid addition of a compound of formula I is preferably a hydrohalide salt preferably hydrochloride.
Preferably, however, the compound of formula I used in the method of the invention is neither in the form of an N-oxide nor an acid addition salt.
In the method according to the invention the locus preferably comprises plants subject to or subjected to fungal attack, seeds of such plants, or the medium in which the plants are growing or are to be grown. The plants are preferably cereal plants, especially barley.
The method of the invention is particularly effective in combating powdery mildews of cereal plants, for example barley powdery mildew.
The locus may conveniently be treated with the compound I at an application rate in the range 0.05-4 kg/ha, preferably 0.1-lkg/ha.
The invention also provides the use of a compound of formula I as defined, as a fungicide.
Further in accordance with the invention there is provided a fungicidal composition comprising an active ingredient of general formula I, as defined above, in association with at least two carriers, at least one of which is a surface-active agent.
A composition according to the invention preferably contains from 0.5 to 95% by weight of active ingredient.
A carrier in a composition according to the invention is any material with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant, seed or soil, or to facilitate storage, transport or handling, A carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid, and any of the carriers normally used in formulating pesticidal compositions may be used. Preferably compositions according to the invention contain 0.5 to 95% by weight of active ingredient.
Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earths; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulphate; ammonium sulphate; synthetic hydrated silicon.
oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulphur; natural and synthetic resins, for example coumarone resins, polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen; waxes; and solid fertilizers, for example superphosphates.
Suitable liquid carriers include water; alcohols, for example isopropanol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic or araliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kerosene and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, perchloroethylene and trichloroethane. Mixtures of different liquids are often suitable.
Agricultural compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application.
The presence of small amounts of a carrier which is a surface-active agent facilitates this process of dilution. Thus preferably at least one carrier in a composition according to the invention is a surfaceactive agent. For example the composition may contain at least two carriers, at least one of which is a surface-active agent.
A surface-active agent may be an emulsifying agent, a dispersing agent or a wetting agent; it may be nonionic or ionic. Examples of suitable surface-active agents include the sodium or calcium salts of polyacrylic acids and lignin sulphonic acids; the condensation of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitol, sucrose or pentaerythritol; condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example - octylphenol or p-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates such as dodecylbenzene sulphonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.
The compositions of the invention may for example be formulated as wettable powders, dusts, granules, solutions, emusifiable concentrates, emulsions, suspension concentrates and aerosols.
Wettable powders usually contain 25, 50 or 75% w of active ingredient and usually contain in addition to solid inert carrier, 3-10% w of a dispersing agent and, where necessary, 0-10% w of stabiliser(s) and/or other additives such as penetrants or stickers. Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and are diluted in the field with further solid carrier to give a composition usually containing 0.5-108 w of active ingredient. Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676 - 0.152 mm), and may be manufactured by agglomeration or impregnation techniques.Generally, granules will contain 0.5-75% w active ingredient and 0-10% w of additives such as stabilisers, surfactants, slow release modifiers and binding agents. The socalled "dry flowable powders" consist of relatively small granules having a relatively high concentration of active ingredient. Emulsifiable concentrates usually contain, in addition to a solvent and, when necessary, co-solvent, 10-50% w/v active ingredient, 2-20% w/v emulsifiers and 0-20% w/v of other additives such as stabilisers, penetrants and corrosion inhibitors.
Suspension concentrates are usually compounded so as to obtain a stable, non-sedimenting flowable product and usually contain 10-75% w active ingredient, 0.5-15% w of dispersing agents, 0.1-10% w of suspending agents such as protective colloids and thixotropic agents, 0-10 w w of other additives such as defoamers, corrosion inhibitors, stabilisers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation or as anti-freeze agents for water.
Aqueous dispersions and emulsions, for example compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the invention. The said emulsions may be of the water-in-oil or of the oil in water type, and may have a thick "mayonnaise" - like consistency.
The composition of the invention may also contain other ingredients, for example other compounds possessing herbicidal, insecticidal or fungicidal properties.
In accordance with a further aspect of the invention there is provided novel compounds of formula I, the compounds being as defined above in relation to the method of the invention, provided that R1 is not a methyl group when R2 is an unsubstituted phenyl group.
In accordance with a further aspect of the invention there is provided a method for the preparation of the novel compounds of formula I, which method comprises reacting together compounds of formulae II and III R1-CO-Q R2-NHCN (Il) (III) where Q is a leaving moiety.
The leaving moiety Q is suitably a halogen, especially chlorine, atom, or a hydroxy group.
The reaction is preferably carried out in the presence of an organic solvent, suitably at a temperature in the range 0-600C, conveniently at ambient temperature.
In a preferred method of preparing novel compounds of formula I, the leaving moiety is a halogen, preferably chlorine, atom, and the reaction is carried out in an inert organic solvent, for example a halogenated hydrocarbon, for example dichloromethane, an ether, for example, diethyl ether, or an aromatic hydrocarbon, for example benzene. Benzene is a preferred solvent. The reaction is preferably carried out in the presence of an acid scavenger, preferably an amine base, for example triethylamine.
In an alternative method if preparing novel compounds for formula I, Q represents a hydroxy group, and the reaction is suitably effected in the presence of acetone and dicyclohexylcarbodiimide.
Compounds of formula II'and III are available products or may be prepared by standard methods.
The invention is further illustrated by the following examples.
Example 1 Preparation of N- (4-chlorophenyl-N-cyano-2- (4-chlorophenyl)-3-methylbutyramide A solution of 2-(4-chlorophenyl)-3-methylbutyryl (2.31g, 0.01M) in 25ml diethyl ether was added dropwise to a solution of 4-chlorophenyl cyanamide (1.52g, 0.01M) and triethylamine (1.01g, 0.01M) in diethyl ether (25ml) at ambient temperature. The reactants were stirred for 15 minutes at room temperature than water (10 ml) was added. The organic layer was separated, washed with water and dried over magnesium sulphate. Evaporation of solvent yielded an orange oil which was purified by chromatography (SiO2/CH2C12) to afford the title compound (1.6g, 46%).
Analysis Calculated : 62.2 4.6 8.1% CHN Found : 60.7 4.5 7.6 Example 2 Preparation of N-(4-chlorophenyl)-N-cyano-2 (4-chlorophenyl-2-methoxyacetamide Dicyclohexycarbodiimide (0.01M, 2.06g) was slowly added to a stirred solution of alphamethoxy-4 chlorophenylacetic acid (0.01M, 1.52g) in dichloromethane (15ml) and the mixture was stirred for 15 minutes. 4-Chlorophenyl cyanamide (0.01M, 1.52 g) was then added to the mixture and stirred for 2 hours at room temperature. The white precipitate was removed by filtration and the filtrate washed with water (lOml) followed by saturated sodium bicarbonate (10ml). The organic layer was dried over magnesium sulphate. After evaporation of solvent, the crude oil was purified by chromatography (SiO2/CH2C12) to afford the title compound (0.6g, 48%), which was an oil.
Analysis Calculated : 57.3 3.6 8.4 CHN Found : 54.5 3.9 8.4 Further compounds were prepared according to procedures similar to those described above. Data on these compounds are set out in Table 1 below, in which the compounds described are in accordance with the general formula
In the following table, substituent groups R1 and R2 are designated by symbols A - ZY. The relation between the substituent groups and the symbols is given in Table 2 below.
Example 33 was prepared by the Wittig reaction of 3,4,5-trimethoxybenzaldehyde with (isopropoxycarbonylmethylene) triphenylphosphorane, to give isopropyl-3,4,5-trimethoxycinnamate, which was hdrolysed with sodium hydroxide, then the resultant acid reacted with thionyl chloride, then the acid chloride reacted as per Example 1.
Examples 68-70 were prepared by reacting a solution of ethyl-2-chloroacetate in benzene with mercaptoethanol/potassium hydroxide solution in methanol, at less than 300C. After stirring for 3 hours at room temperature the mixture was filtered and solvents removed by evaporation. The residue was dissolved in benzene, acidified with p-toluenesulphonic acid, and refluxed for 3 hours. After work-up 2, 3-dihydro-5-ethoxycarbonyl-6-methyl-1 ,4-oxathiin was obtained as a yellow oil (b.p. 102-1060C at 0.7mm Hg).
After saponification (acetic acid/sodium hydroxide) and treatment with thionyl chloride, the acid chloride was condensed with the appropriate phenylcyanamide as per the reaction of Example 1.
The compounds of Examples 71-75 were prepared by oxidation of the compounds of Examples 68-70, using hydrogen peroxide in acetic acid at 40-500C. The resulting mixture of sulphoxides and sulphones was separated by flash chromatography on silica gel using 1:1(v:v) diethyl ether:dichloromethane as eluant.
Also presented in Table 1 below is data on the fungicidal activity of the compounds, their activity being investigated by means of the following tests.
(a) Direct protectant activity against vine downy mildew (Plasmopara viticola; Pvp) The test is a direct protectant one, using a foliar spray. The lower surfaces of leaves of whole vine plants (cv Cabernet Sauvignon) are sprayed with a solution of active material in l:lv/v water/acetone containing 0.04%w "Triton X-155" (trade mark) (octylphenol polyoxyethylene surfactant), at a dosage of 1 kilogram of active material per hectare using a track sprayer which delivers 620 litres/ha, and after a subsequent 24 hours under normal glasshouse conditions the lower surfaces of the leaves are inoculated by spraying with an aqueous solution containing 104 zoosporangia/ml. The inoculated plants are kept for 24 hours in a high humidity compartment, 5 days under normal glasshouse conditions and then returned for a further 24 hours to high humidity.Assessment is based on the percentage of leaf area covered by sporulation compared with that on control leaves.
(b) Antisporulant activity against vine downy mildew (Plasmopara viticola; Pva) The test is a direct antisporulant one using a foliar spray. The lower surfaces of leaves of whole vine plants (cv Cabernet Sauvignon) are inoculated by spraying with an aqueous suspension containing 104 zoosporangia/ml 2 days prior to treatment with the test compound. The inoculated plants are kept for 24 hours in a high humidity compartment, and then 24 hours at glasshouse ambient temperature and humidity. When the plants are dry, infected leaves are sprayed on their lower surfaces with a solution of active material in 1:1 water/acetone containing 0.04% w/w "Triton X-155" (trade mark) (an octylphenol polyethoxylate surfactant).
The spraying is carried out with a moving track sprayer with delivers 620 litre/ha, and the concentration o active material is calculated to give an application rate of lkg/ha. After spraying, the plants are returned to normal glasshouse conditions for 5 hours and are then transferred to the high humidity compartment for 24 hours to induce sporulation, prior to assessment.
Assessment is visual and is based on the percentage of the leaf area covered by sporulation compared with that on control leaves.
(c) Activity against wheat leafspot (Leptosphaeria nodorum; Ln) The test is a direct antisporulant one, using a foliar spray. Leaves of wheat plants (cv Mardler), at the single leaf stage, are inoculated by spraying with an aqueous suspension containing 8 x 105 spores/ml. The inoculated plants are kept for 24 hours in a high humidity compartment prior to treatment. The plants are sprayed at a dosage of 1 kg. of active material per hectare using a track sprayer as described under (a).
After drying, the plants are kept for 5 days under normal glasshouse conditions, followed by assessment.
Assessment is based on the percentage of leaf area covered by sporulation compared with that on leaves of control plants.
(d) Activity against barley powdery mildew (Erysiphe graminis f.sp. hordei; Eg) The test is a direct antisporulant one, using a foliar spray. Leaves of barley seedlings, cultivar Golden Promise, are inoculated by dusting with mildew conidia one day prior to treatment with the test compound. The inoculated plants are kept overnight at glasshouse ambient temperature and humidity prior to treatment. The plants are sprayed at a dosage of lkg.
of active material per hectare using a track sprayer as described under (a). After drying, plants are returned to a compartment at ambient temperature and humidity for up to 7 days, followed by assessment. Assessment is based on the percentage of leaf area covered by sporulation compared with that on leaves of control plants.
(e) Activity against wheat eyespot (Pseudocereosporlla herpotrichoides; Ph).
The test is an in vitro one. Samples are prepared wherein 0.7 mls solution containing 2 mg active material dissolved in acetone is evenly dispersed in 20ml molten half-strength potato dextrose agar (formed by dissolving 2g potato extract, 10g dextrose and 7.5g agar in 1 litre of water and sterilising for 15 minutes at 1210C) and the resulting 20ml portions are allowed to set in 9cm petri dishes. The concentration of active material in the resulting samples is 100ppm. Upon setting, two plugs of 5mm diameter taken from the advancing edge of a stock plate of a 3 to 4 week old culture of P.herpotrichoides on full strength potato dextrose agar, incubated at 20-220C in darkness, are placed, equally spaced on the surface of each sample, mycelial side uppermost. The samples are incubated for 11 days at 20-220C in darkness before assessment.
Diametric growth is measured with the width of the plug subtracted and results compared with growth on a sample wherein 0.7ml acetone containing no active material is dispersed in 20ml half-strength potato agar.
(f) Activity against broad bean rust (Uromyces fabae; Uf) The test is a translaminar antisporulant one using foliar spray. Pots containing 1 plant per pot were inoculated by spraying an aqueous suspension, containing 5 x 104 spores/ml plls a little "Triton X155" (trade mark), onto the undersurface of each leaf 20-24 hours before treatment with test compound. The inoculated plants were kept overnight in a high humidity compartment, dried at glasshouse ambient temperature and then sprayed, on the leaf upper surface, at a dosage of lkg/ha of active material using a track sprayer as described under (a). After treatment the plants were kept at glasshouse temperature and assessment made 11-14 days after treatment. Symptoms are assessed on the relative density of sporulating pustules per plant compared with that on control plants.
(g) Activity against wheat brown rust (puccinia Recondita; Pr) The test is a direct protectant one using' a foliar spray. Wheat seedlings (cv Brigand) are grown to the 1-1.5 leaf stage. The plants are then sprayed with the test.compound at a dosage of 1 kg/ha using a track sprayer as described under (a). Test compounds are applied as solutions or suspensions in a mixture of acetone and water (50:50 V/v) containing 0/04% surfactant ("TWEEN 20" - Trade Mark) 18-24 hours after treatment, the seedlings are inoculated by spraying the plants from all sides with an aqueous spore suspension containing about 105 spores/ml.
For 18 hours after inoculation, the plants are kept in high humidity conditions at a temperature of 20-220C.
Thereafter, the plants are kept in ambient glasshouse conditions, that is, in moderate relative humidity and at a temperature of 20 C.
The disease is assessed 10 days after inoculation by sporulating pustules compared with that on the control plants.
(h) Activity against Wheat root rot (Fusarium species; Fs) This test measures the in vitro activity of compounds against a species of Fusarium that causes stem and root rot.
Compound is dissolved'or suspended in acetone and added to molten half strength Potato Dextrose Agar to give final concentration of 100ppm compound and 3.5% acetone. After the agar has set, plates are inoculated with 6mm diameter plugs of agar and mycelium taken from a 7 day old culture of Fusarium sp..
Plates are inoculated at 200C for 5 days and radial growth from the plug is measured.
(i) Direct protectant activity against vine grey mould (Botrytis cinerea; Bcp) The test is a direct protectant one using a foliar spray and is effected as described under (a), with the difference that the leaves are inoculated by spraying with an aqueous solution containing 105 conidia/ml.
(j) Activity against tomato early blight (Alternaria Solani; As) The test is a direct protectant one using a foliar spray. The upper surfaces of leaves of young tomato plants are sprayed with a solution of active material as described in (a) above. After 24 hours under normal glasshouse conditions, the upper surfaces of the leaves are inoculated by spraying with an aqueous suspension containing 104 spores/ml. The inoculated plants are kept for 72 hours in a high humidity compartment and are then removed to lower humidity (5070% relative humidity). Assessment is made 8 days after inoculation.
(k) Activity against rice leaf blast (Pyricularia oryzae; Po) The test is a direct eradicant one using a foliar spray. The leaves of rice seedlings (about 30 seedlings per pot) are sprayed with an aqueous suspension containing 105 spores/ml 20-24 hours prior to treatment with the test compound. The inoculated plants are kept overnight in high humidity and then allowed to dry before spraying at a dosage of lkg of active material per hectare using a track sprayer as described under (a).
After treatment the plants are kept in a rice compartment at 25-300C and high humidity. Assessments are made 4-5 days after treatment and are based on the density of necrotic lesions and the degree of withering when compared with control plants.
TABLE 1 Ex. No. R1 R2 mp( C) Analysis % Fungicidal C H N Calc. Activity Found 3 A B oil 71.2 5.2 6.9 Fs-1 69.0 5.3 5.9 4 C B oil 62.8 4.5 7.0 Ph-1, Fs-1, 59.5 4.5 5.7 Uf-I, Pc-l 5 D E 96-98 66.5 4.1 10.4 Fs-2, Ph-1 66.4 4.2 10.4 Pvp-1, Pr-i 6 F E oil 72.7 4.3 8.1 Pr-1, Bcp-1 73.4 4.8 8.1 7 G E 125-126 59.0 3.3 9.2 Pvp-2, As-2, 58.4 3.4 9.3 Pr-2 8 H E oil 60.2 3.4 8.8 Pr-2, Pvp-1 59.5 4.0 8.1 Ph-l, Fs-1 9 I E 158-160 58.2 4.5 19.4 Pvp-2, As-2 57.3 4.8 19.0 Bcp-1, Pr-l 10 J E 160-163 56.7 4.0 20.4 Pvp-2, Ph-2 54.8 4.7 18.3 Fs-2, Pr-l 11 K E oil 66.6 5.5 8.2 Eg-2 64.3 5.4 7.7 12 L E oil 64.6 6.8 10.1 As-2, Fs-1 65.0 6.9 9.8 13 M E 103-105 58.6 3.8 19.5 Pvp-2, Ph-2 55.5 3.9 18.0 Fs-2, As-l 14 N E 133-134 61.7 4.5 8.5 As-2, Ph-1 61.6 4.6 8.7 Bcp-1, Ln-1 15 A O oil 62.2 4.6 8.1 As-2, Pvp-1 61.2 4.8 7.7 Ln-1 16 A P oil 62.2 4.6 8.1 As-2, Eg-2 60.1 4.8 7.9 Pvp-1 17 Q E oil 68.3 5.0 9.4 Fs-1 68.7 5.5 8.4 18 R E oil 60.2 3.4 8.8 Pvp-1, Bcp-1 60.4 3.8 8.8 Pr-1, As-i 19 S E 138-141 53.0 2.7 8.8 Pva-1 53.1 2.9 8.7 20 T E 92-95 68.3 5.0 9.4 As-2, Pvp-1 67.8 5.5 10.5 Pva-1 21 U E 90-93 59.0 3.3 9.2 Pvp-2, Ph-i 58.7 3.5 9.6 Fs-1, Bcp-1 Table 1 (continued) Ex. No. R1 R2 mp( C) Analysis % Fungicidal C H N Calc.Activity Found 22 V E 96-98 60.6 3.1 16.3 Bcp-2, Ph-2 60.2 3.0 16.0 Fs-2, Pvp-1 23 W E 125-127 60.6 3.1 16.3 Ph-2, Fs-2 59.6 2.9 15.8 pvp-2, bcp-2, Pr-1 24 X E 128-130 65.5 3.5 10.9 Fs-2, Pr-l 65.1 3.7 10.9 Ph-1 25 Y E 151-153 68.0 3.9 9.9 Ph-1, Fs-1 68.0 4.1 9.9 26 Z E 106-108 51.6 2.2 8.6 51.6 2.3 8.6 27 ZA E 71-72 55.5 3.6 14.4 Ph-2 Fs-2 55.4 3.7 13.9 28 E E 153-155 57.7 2.8 9.6 Pvp-1, As-l 58.0 2.9 9.6 29 ZB E 215-220 53.1 3.1 14.3 Pr-l 51.8 3.1 13.6 30 ZC E 67-68 60.9 5.5 11.8 Ph-2, Fs-2 60.2 5.2 11.6 31 ZD E 143-144 60.6 3.2 8.8 60.0 3.4 8.7 32 ZE E 141-145 54.6 2.6 8.0 As-2 56.5 3.1 7.5 33 ZF E 148-150 61.2 4.6 7.5 60.1 4.7 7.1 34 ZG E 136-138 68.8 4.4 9.4 67.1 4.4 9.5 35 ZH E 161-163 55.3 3.5 21.5 Ph-2 Fs-2 54.1 3.7 20.5 Pvp-2, Bcp-2 Pr-1, As-1 36 ZI E 128-131 54.8 '3.6 9.1 Pvp-2, As-2 54.5 3.8 9.0 Fs-1 37 G ZJ oil 53.0 2.7 8.2 Pvp-2, Ph-2 53.5 3.1 8.5 Pr-1, Fs-1 38 ZK E 62-64 56.4 3.3 10.1 Ph-2, Pr-l 57.2 3.5 10.3 As-1, Pvp-1, Fs-1 39 ZL E 55-57 56.4 3.3 10.1 Ph-2, Pvp-2 57.2 3.5 10.4 Pr-1, As-1, Fs-1 40 V ZJ 148-150 53.4 2.4 14.4 Bc---2, Ph-2 52.8 2.8 1.0 Fs-2, As-1 Table 1 (continued) Ex. No.R1 R2 mp( C) Analysis % Fungicidal Found 41 V G 65-67 61.9 3.7 15.5 Bcp-2, Ph-2 61.2 3.8 15.6 Fs-2, Pr-l As-1 42 W ZJ 213-216 53.4 2.4 14.4 Pvp-2, As-2 50.8 3.3 14.2 Eg-1, Pr-1 43 ZH G oil 56.8 4.0 20.4 Pvp2, Ln-1 55.8 4.6 18.6 Pol 44 ZH ZJ oil 48.8 2.7 19.0 Pvp-2, As-1 46.7 3.1 17.6 Fs-1 45 ZH ZM oil 66.1 5.5 22.0 Fs-1 64.0 5.7 20.4 46 G ZN oil 59.5 4.4 7.7 58.2 4.5 7.3 47 P E 68-70 57.7 2.8 9.6 Ln-2, Pr-2 57.5 2.9 9.7 Ph-1, Es-i 48 P X 88-90 65.6 3.5 10.9 Pvp-1, Pr-l 65.2 3.7 10.9 Fs-1 49 P ZO 88-90 50.1 2.4 8.4 Pvp-2, Ln-2 49.8 2.6 8.3 Pr-l 50 P ZP 115-116 61.3 2.9 10.2 Pvp-2, Ln-1 60.8 3.0 10.1 51 ZH ZO 168-169 47.2 3.0 18.4 Ph-2, Fs-2 46.7 2.9 17.7 Pr-1, As-1 52 ZR X oil 69.0 4.4 12.4 Ph-1, Fs-1 68.1 4.5 12.2 53 ZR E 158-162 60.0 3.5 10.8 Pr-2, Bcp-1 58.8 3.8 10.7 As-1, Es-i 54 ZS X 173-175 48.3 2.6 8.0 Pr-2, Fs-1 47.0 3.3 8.1 55 ZS E 203-204 44.0 2.1 7.3 42.8 2.8 7.2 56 ZS ZO 210-212 39.3 1.9 6.6 36.9 2.5 6.7 57 ZS ZP 190-192 45.9 2.2 7.7 As-1 46.5 3.3 7.4 58 ZT X 74-76 76.3 5.1 11.9 Pr-2, Es-i 79.9 5.1 11.8 59 ZT E 118-120 66.7 4.1 10.4 65.5 3.9 10.4 Table 1 (continued) Ex. No. R1 R2 mp( C) Analysis % Fungicidal C H N Calc.Activity 60 ZT ZO 122-123 57.1 3.5 8.9 56.9 3.4 8.8 pv1 61 ZT ZP 116-118 70.9 4.3 11.0 Pvp-2 70.5 4.2 11.0 62 ZU ZV oil 68.3 7.3 11.4 Ln-1 68.3 7.6 11.2 63 ZU X oil 70.0 5.0 11.7 Ph-1, Fs-1 64 ZU E 67-70 61.2 4.0 10.2 Pr-2, Fs-1 60.7 4.1 9.3 65 ZU ZO 92-94 52.7 3.5 8.8 Pr-2, Pvp-1 52.7 3.4 8.6 Fs-1 66 ZU ZP 78-80 65.1 4.3 10.9 Pvp-2, Ph-1 64.6 4.6 9.7 Fs-1 67 ZW X oil 60.0 4.6 10.8 Pr-2 Fs-2 59.7 4.9 10.4 Pvp-1, Ph-1 68 ZW E oil 53.1 3.7 9.5 Pr-2, Fs-2 52.2 4.3 8.1 Pvp-1 69 ZW ZO 89-91 46.0 3.2 8.3 Pr-2 Fs-2 44.9 3.6 7.2 70 ZW ZP oil 56.1 4.0 10.1 Pr-2, Fs-1 55.1 4.5 8.3 71 ZY E 137-139 47.8 3.4 8.6 Pvp-1, Pr-1 47.2 3.8 7.2 Po-1, As-1 72 ZX E oil 50.3 3.6 9.0 As-1, Fs-1 48.9 3.6 9.1 73 m zo 177-179 42.0 3.0 7.6 Pvp-1, Pr-1 42.4 3.2 8.0 Fs-1 74 ZX ZO oil 43.9 3.1 7.9 Pr-1, Fs-1 43.8 3.0 7.9 75 ZY ZP 134-135 50.3 3.6 9.0 50.1 3.8 9.1 1 A E oil 62.2 4.6 8.1 Eg-2, As-1 60.7 4.5 7.6 2 ZQ E oil 57.3 3.6 8.4 Pvp-1 54.5 3.9 8.4 TABLE 2

Claims (14)

  1. CLAIMS 1. A method of combating fungus at a locus, characterised by treating the locus with a fungicidally effective amount of a compound of general formula
    in which R1 represents an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted phenyl group, an optionally substituted heterocyclic group which is connected by a ring carbon atom to the group -CO-, or a group of formula R3-X-, where R3 represents an optionally substituted phenyl group or an optionally substituted heterocyclic group which is connected by a ring carbon atom to the group X, and x represents an optionally substituted alkylene or alkenylene group, cr a group of formula -SO2-; and R2 represents an optionally substituted cycloalkyl, phenyl or phenalkyl group; including any such compounds in the form of N-oxides and acid addition salts.
  2. 2. A method as claimed in Claim 1, wherein R1 represents a l,l-dimethyl-2-(2,2-dichlorovinyl)- cyclopropyl group; or a phenyl group optionally substituted by 1-3 moieties independently selected from halogen atoms and C14 alkyl groups; or a pyridyi, furyl, imidazole, or 2,3-dihydro-1,4-oxathiin group, optionally S-oxidised, any such group being optionally substituted by 1-3 C14 alkyl or C24 alkenyl groups; or a group of formula R3-X, where R3 represents a phenyl group optionally substituted by 1-3 moieties independently selected from halogen atoms and C1-4 alkyl and C14 alkoxy groups, or a heteroaryl group optionally substituted by 1-3 C1-4 alkyl groups, and X represents a C1-6 alkylene group, linear or branched, optionally substituted by a phenyl or C14 alkoxy group; or a C34 alkenylene group; or a group of formula -SO2-.
  3. 3. A method as claimed in Claim 1 or 2, wherein R1 represents a C1-8 alkyl group; a phenyl group optionally substituted by 1-2 moieties independently selected from halogen atoms and C14 alkyl groups; an imidazole or furyl group , connected by a ring carbon atom to the group -CO-, and optionally substituted by 1 or 2 C14 alkyl or C24 alkenyl groups; or.a 5-(2,3-dihydro-6-methyl-1,4-oxathiin) group, optionally S-oxidised; or a group of formula R3-X- where R3 represents a phenyl group optionally substituted by 1-3 moieties independently selected from halogen atoms, and C14 alkyl and C1-4 alkoxy groups, or R3 represents a thienyl group connected by a ring carbon atom to the group X, and optionally substituted by 1-2 C1-4 alkyl groups, and X represents a group of formula -CHY- where Y represents a hydrogen atom or a C15 alkyl group, or X represents a C3-4 alkenylene group.
  4. 4. A method as claimed in any preceding claim, wherein R1 represents an optionally substituted imidazole group of formula
    where Z represents a C14 alkyl group; or R1 represents a group of formula R3-X- where R3 represents a halophenyl group and X represents a group of formula -CHY- where Y represents a C14 alkyl group.
  5. 5. A method as claimed in any preceding claim, wherein R2 represents a phenyl group optionally substituted by 1-3 moieties independently selected from phenoxy groups and halogen atoms; or a phenalkyl group, being a phenyl group optionally substituted by 1-3 halogen atoms, bonded to a cl-a alkylene group; or a C38 cycloalkyl group.
  6. 6. A method as claimed in any preceding claim, wherein R2 represents a halophenyl group carrying 1 or 2 halogen atoms, or a halobenzyl group having a halophenyl group carrying 1 or 2 halogen atoms.
  7. 7. A method as claimed in any preceding claim, wherein R2 represents a 4-chlorophenyl group.
  8. 8. Use of a compound of the general formula I, as defined by any preceding claim, as a fungicide.
  9. 9. A fungicidal composition comprising an active ingredient of general formula I, as defined in any preceding claim, in association with at least two carriers, at least one of which is a surface-active agent.
  10. 10. A novel compound of the general formula I, being a compound as defined in any preceding claim, provided that R1 is not a methyl group when R2 is an unsubstituted phenyl group.
  11. 11. A process for the preparation of a compound as claimed in Claim 10, which process comprises reacting together compounds of formulae II and III R1-CO-Q (II) R2-NHCN (Il) (III) where Q is a leaving moiety.
  12. 12. A process as claimed in Claim 11, wherein Q is a halogen atom, and the reaction is carried out in the presence of an inert organic solvent and an acid scavenger, at a temperature in the range 0-600C; or Q is a hydroxyl group, and the reaction is carried out in the presence of acetone and dicyclohexylcarbodiimide, at a temperature in the range 0-600C.
  13. 13. A compound of formula I, as claimed in Claim 10, when prepared by a process as claimed in Claim 11 or 12.
  14. 14. A method of combating a fungus at a locus, and/or a fungicidal composition, and/or a novel compound of formula I and/or a process for the preparation of such a novel compound, substantially as hereinbefore described with particular reference to the Examples.
GB8900257A 1989-01-06 1989-01-06 Fungicidal n-acyl cyanamides Withdrawn GB2226815A (en)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2462011A1 (en) * 1973-11-14 1975-06-26 Soissonnais Sucrerie CYANAMIDE DERIVATIVES
DE2908775A1 (en) * 1978-03-11 1979-09-13 Konishiroku Photo Ind METHOD FOR GENERATING COLOR PICTURES
EP0087392A2 (en) * 1982-02-23 1983-08-31 Ciba-Geigy Ag Cyanacyl amide derivatives and preparation thereof
EP0087394A2 (en) * 1982-02-23 1983-08-31 Ciba-Geigy Ag Process for the preparation of N-substituted N-cyano-amides and their use
EP0088047A1 (en) * 1982-02-23 1983-09-07 Ciba-Geigy Ag N-cyanocarboxylic acid amides, process for their preparation and their use
JPS59175407A (en) * 1983-03-24 1984-10-04 Kyowa Gas Chem Ind Co Ltd Herbicide
JPS63264571A (en) * 1987-04-20 1988-11-01 Aguro Kanesho Kk Pyridyl-2-oxy-phenoxy-propionic acid amide derivative
DE3717815A1 (en) * 1987-05-27 1988-12-15 Bayer Ag Fungicidal compositions based on substituted cyanamides

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2462011A1 (en) * 1973-11-14 1975-06-26 Soissonnais Sucrerie CYANAMIDE DERIVATIVES
DE2908775A1 (en) * 1978-03-11 1979-09-13 Konishiroku Photo Ind METHOD FOR GENERATING COLOR PICTURES
EP0087392A2 (en) * 1982-02-23 1983-08-31 Ciba-Geigy Ag Cyanacyl amide derivatives and preparation thereof
EP0087394A2 (en) * 1982-02-23 1983-08-31 Ciba-Geigy Ag Process for the preparation of N-substituted N-cyano-amides and their use
EP0088047A1 (en) * 1982-02-23 1983-09-07 Ciba-Geigy Ag N-cyanocarboxylic acid amides, process for their preparation and their use
JPS59175407A (en) * 1983-03-24 1984-10-04 Kyowa Gas Chem Ind Co Ltd Herbicide
JPS63264571A (en) * 1987-04-20 1988-11-01 Aguro Kanesho Kk Pyridyl-2-oxy-phenoxy-propionic acid amide derivative
DE3717815A1 (en) * 1987-05-27 1988-12-15 Bayer Ag Fungicidal compositions based on substituted cyanamides

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* Cited by examiner, † Cited by third party
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CA 95(11) : 97305A *

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