WO2003074491A1 - O-cyclopropyl-carboxanilides and their use as fungicides - Google Patents

O-cyclopropyl-carboxanilides and their use as fungicides Download PDF

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Publication number
WO2003074491A1
WO2003074491A1 PCT/IB2003/000687 IB0300687W WO03074491A1 WO 2003074491 A1 WO2003074491 A1 WO 2003074491A1 IB 0300687 W IB0300687 W IB 0300687W WO 03074491 A1 WO03074491 A1 WO 03074491A1
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Prior art keywords
formula
compound
hydrogen
optionally substituted
alkyl
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PCT/IB2003/000687
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French (fr)
Inventor
Josef Ehrenfreund
Hans Tobler
Harald Walter
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Syngenta Participations Ag
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Priority claimed from GB0205127A external-priority patent/GB0205127D0/en
Priority claimed from GB0300705A external-priority patent/GB0300705D0/en
Priority to MXPA04008314A priority Critical patent/MXPA04008314A/en
Priority to JP2003572960A priority patent/JP4511191B2/en
Priority to US10/506,918 priority patent/US7951752B2/en
Priority to CA2477931A priority patent/CA2477931C/en
Priority to EP03706779A priority patent/EP1480955B1/en
Priority to SI200330951T priority patent/SI1480955T1/en
Priority to IL16369203A priority patent/IL163692A0/en
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Priority to KR1020047013715A priority patent/KR100818540B1/en
Priority to DE60314600T priority patent/DE60314600T2/en
Priority to BRPI0308230-0A priority patent/BR0308230B1/en
Priority to DK03706779T priority patent/DK1480955T3/en
Priority to AU2003208490A priority patent/AU2003208490B2/en
Publication of WO2003074491A1 publication Critical patent/WO2003074491A1/en
Priority to ZA2004/06395A priority patent/ZA200406395B/en
Priority to HK05112077.6A priority patent/HK1079785B/en
Priority to US12/420,440 priority patent/US20090197925A1/en
Priority to FR12C0019C priority patent/FR12C0019I2/en
Priority to NL350085C priority patent/NL350085I2/en

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    • 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
    • C07D213/82—Amides; Imides in position 3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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    • C07D207/02—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
    • 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
    • C07D207/34—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 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
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    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings 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
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings 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
    • C07D231/16—Halogen atoms or nitro radicals
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • 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
    • C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
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    • 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
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    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel ortho-substituted-cyclopropyl-azol- carboxamides which have microbiocidal activity, in particular fungicidal activity.
  • the invention also relates to the preparation of these compounds, to novel intermediates used in the preparation of these compounds, to agrochemical compositions which comprise at least one of the novel compounds as active ingredient, to the preparation of the compositions mentioned and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.
  • EP0545099A2 JP06220035 and JP02129171 disclose certain ortho-unsubstituted- cyclopropyl-azol-carboxamides
  • the present invention provides a compound of formula (I):
  • Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by groups R 4 , R 5 and R 6 ;
  • R 1 is hydrogen or halo;
  • R 2 is hydrogen or halo;
  • R 3 is optionally substituted C 2 . 12 alkyl, optionally substituted C 2 - ⁇ 2 alkenyl, optionally substituted C 2 . 12 alkynyl, optionally substituted C 3 .j 2 cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclyl; and
  • R 4 , R 5 and R 6 are, independently, selected from hydrogen, halo, cyano, nitro, C 1.
  • Halo is fluoro, chloro or bromo.
  • Each alkyl moiety is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, w ⁇ -propyl, n-butyl, sec-butyl, w ⁇ -butyl, tert-butyl or neo-pentyl.
  • Alkenyl and alkynyl moieties can be in the form of straight or branched chains.
  • the alkenyl moieties where appropriate, can be of either the (E)- or (Z)-configuration. Examples are vinyl, allyl and propargyl.
  • each optional substituent on alkenyl or on alkynyl is, independently, selected from those optional substituents given above for an alkyl moiety.
  • Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • each optional substituent on cycloalkyl is, independently, selected from Ci_ 3 alkyl and those optional substituents given above for an alkyl moiety.
  • heterocyclyl refers to a non-aromatic or aromatic ring containing up to 10 atoms including one or more (preferably one or two) heteroatoms selected, each independently, from O, S and N.
  • heteroatoms selected, each independently, from O, S and N.
  • examples of such rings include 1,3-dioxolanyl, tetrahydrofuranyl, morpholinyl, thienyl and furyl.
  • each optional substituent on phenyl or on heterocyclyl is, independently, selected from alkyl and those optional substituents given above for an alkyl moiety. When present, there are up to four optional substituents on phenyl, each independently selected.
  • each optional substituent on an alkyl moiety is, independently, selected from the preferred list of halo, hydroxy, methoxy, trifluoromethoxy, difluoromethoxy, cyano and nitro.
  • each optional substituent on alkenyl or on alkynyl is, independently, selected from the preferred list of halo and cyano.
  • each optional substituent on cycloalkyl is, independently, selected from the preferred list of methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy and cyano.
  • each optional substituent on phenyl or on a heterocyclyl group is, independently, selected from the preferred list of halo, hydroxy, methoxy, trifluoromethoxy, difluoromethoxy and cyano. It is prefe ⁇ ed that Het is pyrrolyl, pyrazolyl, thiazolyl, pyridinyl, pyrimidinyl, thiophenyl, furyl, isothiazolyl or isoxazolyl (more preferably pyrrolyl, pyrazolyl or thiazolyl), each being substituted by groups R 4 , R 5 and R 6 .
  • R 1 and R 2 are, independently, hydrogen or fluoro.
  • R 3 is C 2 - 6 alkyl, optionally substituted C 3 . 8 cycloalkyl, phenyl, thienyl or furyl.
  • R 4 , R 5 and R 6 are, independently, selected from hydrogen, halogen, CM alkyl, CM haloalkyl and C ⁇ . 4 alkoxy(C ⁇ . 4 )alkyl; provided that at least one of R 4 , R 5 and R 6 is not hydrogen. More preferably R 4 , R 5 and R 6 are, independently, selected from hydrogen, halogen, methyl, Cj. 2 haloalkyl and methoxymethyl; provided that at least one of R 4 , R 5 and R 6 is not hydrogen.
  • R 3 is as defined above for a compound of formula (I), are also novel and are useful as intermediates in the preparation of compounds of formula (I).
  • the present invention provides a compound of formula (H) where R 3 is as defined above for a compound of formula (I).
  • the compounds of formula (I) and of formula (U) may exist as different geometric or optical isomers or in different tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.
  • Table 1 provides 22 compounds of formula (II) wherein R is as defined in Table
  • Table X represents Table 2 (when X is 2) and represents Table 3 (when X is 3).
  • Table 2 provides 80 compounds of formula (la):
  • R ⁇ R z , R 3 , R 4 , R 5 and R 6 are as defined in Table 3.
  • Table 4 provides 50 compounds of formula (lc):
  • R > 1', R TJf2, R ⁇ j4 * and R 3 are as defined in Table 4.
  • Table 5 provides 54 compounds of formula (Id):
  • R , ⁇ , R , R and R are as defined in Table 5.
  • Table 6 provides 45 compounds of formula (le):
  • R 1 , R 2 , R 3 and R 4 are as defined in Table 6.
  • Table 7 shows selected melting point and selected NMR data, all with CDC1 3 as the solvent (unless otherwise stated; if a mixture of solvents is present, this is indicated as, for example, (CDC1 3 / d ⁇ -DMSO)), (no attempt is made to list all characterising data in all cases) for compounds of Tables 1 to 6.
  • the data relate to a cis/trans mixture of each compound; a compound number which ends with the letter 'c' relates only to its cis-isomer and a compound number which ends with the letter Y relates only to its trans-isomer.
  • a compound of formula (H) [where R 3 is as defined above for a compound of formula (I)] may be prepared by a reaction sequence starting with a crossed-aldol condensation of benzaldehyde with a ketone of formula CH 3 C(O)R [where R is as defined above for a compound of formula (I)] in the presence of NaOH or KOH in a solvent (such as water or ethanol) and usually under reflux conditions or alternatively by reaction of benzaldehyde with a Wittig reagent under standard conditions.
  • a solvent such as water or ethanol
  • ⁇ . ⁇ -unsaturated ketone of formula (UI) [where R 3 is as defined above for a compound of formula (I)]: may then be converted into a compound of formula (IV) [where R 3 is as defined above for a compound of formula (I)]:
  • a compound of formula (II) may then be separated and catalytically reduced (Pt/C/H 2 or Ra-Ni/H 2 ) in a solvent (such as methanol, ethanol or THF) at room temperature, to produce a crude o/p-mixture of a compound of formula (II), which may be further purified by standard techniques.
  • a solvent such as methanol, ethanol or THF
  • a compound of formula (II) [where R 3 is as defined above for a compound of formula (I)] may be prepared by a process as illustrated by the following reaction sequence and which involves a Pd(H)-catalysed imination step.
  • a compound of formula (NHI) [where R 3 is as defined above for a compound of formula (I)] is added to bromine and methanol at a temperature of 5-10°C, after which triphenylphosphine in a solvent [such as tetrahydrofuran] is added, to produce a compound of formula (IX) [where R is as defined above for a compound of formula (I)], which in turn is added to sodium hydride, in a solvent [such as DMSO], and then reacted with 2-bromobenzaldehyde or 2-iodobenzaldehyde to yield a compound of formula (X) [where R 3 is as defined above for a compound of formula (I) and Hal is bromo or iodo].
  • the resultant compound of formula (X) is then mixed with hydrazine hydrate in a solvent [such as ethanol] and heated to reflux, after which potassium hydroxide is added and the resultant reaction mixture is maintained at 200-220°C for several hours.
  • a standard extraction and purification procedure yields a compound of formula (XI) [where R is as defined above for a compound of formula (I) and Hal is bromo or iodo] which may then be converted to a compound of formula (H) by mixing with benzophenone imine, sodium tertiary butoxide, tris-dibenzylideneacetone- dipalladium (Pd j dba j ), racemic 2,2'-bis(diphenylphosphino)-l,l'-binaphthyl (BI ⁇ AP) and a solvent [such as benzene or toluene] and heating at reflux temperature, typically for several hours, and adding the resultant [usually crude isolated] imine to a mixture
  • the resultant mixture is stirred, preferably for about an hour at room temperature, after which a cis-/trans-mixture of a compound of formula (II) may be extracted and subsequent separation of the cis- and trans-isomers achieved by using flash chromatography.
  • Reaction scheme IB is novel and inventive, particularly the use of a Pd(II)-catalysed imination step. Therefore in a still further aspect the present invention provides a process for preparing a compound of formula (II), where R 3 is as defined above, comprising at least one of the steps of reaction scheme IB; in particular a step using a Pd(II)catalys ⁇ -ligand-system [where the ligand is selected from a suitable sterically demanding phosphine (for example BINAP or dppf)] to react a compound of formula (XT) [where Hal is bromo or iodo; and R 3 is as defined above] with benzophenone imine optionally in the presence of a base [such as sodium-tert- butanolate, potassium-tert-butananolate, sodium carbonate, potassium carbonate or cesium carbonate] to produce a compound of formula (XII) [where R 3 is as defined above].
  • a base such as sodium-
  • R 3 ⁇ is hydrogen or methyl
  • a strong base such as NaH in a solvent such as DMSO
  • a base such as triethylamine, Hunig base, sodium bicarbonate, sodium carbonate, potassium carbonate, pyridine or quinoline, but preferably triethylamine
  • a solvent such as diethylether, TBME, THF, dichlor
  • a coupling agent such as benzotriazol-1- yloxytris(dimethylamino) phosphoniumhexafluorophosphate, bis-(2-oxo-3- oxazolidinyl)-phosphinic acid chloride, N,N'-dicyclohexylcarbodiimide or 1,1'- carbonyl-diimidazole] may be used.
  • R 3 ⁇ is hydrogen or methyl
  • R 3 ⁇ may be prepared by the reduction of the nitro group of a compound of formula (VI) [where R 3A is hydrogen or methyl] using standard conditions (for example, catalytic reduction or Bechamp-reduction) followed by amidation with an acid chloride to provide a compound of formula (VII) [where R 3A is hydrogen or methyl]
  • novel compounds of formula (I) have, for practical purposes, a very advantageous spectrum of activities for protecting plants against diseases that are caused by fungi as well as by bacteria and viruses.
  • the compounds of formula (I) can be used in the agricultural sector and related fields of use as active ingredients for controlling plant pests.
  • the novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous cultivated plants.
  • the compounds of formula I can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
  • compounds of formula (I) are used as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
  • the compounds according to present invention may be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management, etc.
  • the compounds of formula (I) are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g.
  • Botrytis Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Altemaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia). Additionally, they are also effective against the Ascomycetes classes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and of the Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara). Outstanding activity has been observed against powdery mildew (Erysiphe spp.). Furthermore, the novel compounds of formula I are effective against phytopathogenic bacteria and viruses (e.g. against Xanthomonas spp, Pseudomonas spp, Erwinia amylovora as well as against the tobacco mosaic virus).
  • Basidiomycetes e.g. Rhizoctonia, Hemileia, Puccinia
  • target crops to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco
  • the compounds of formula (I) are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances.
  • the methods of application such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.
  • the compounds of formula (I) are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g.
  • fertilizers or micronutrient donors or other preparations which influence the growth of plants can also be selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • the compounds of formula (I) can be mixed with other fungicides, resulting in some cases in unexpected synergistic activities.
  • Mixing components which are particularly preferred are azoles, such as azaconazole, BAY 14120, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imiben- conazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, pyrifenox, prochloraz, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole; pyrimidinyl carbin
  • a preferred method of applying a compound of formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application.
  • the frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen.
  • the compounds of formula I can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field.
  • the compounds of formula I may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • a formulation that is, a composition containing the compound of formula (I)] and, if desired, a solid or liquid adjuvant, is prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • extenders for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • the agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula I, 99.9 to 1 % by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
  • Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from lOg to 1kg a.iVha, most preferably from 20g to 600g a.i./ha.
  • convenient dosages are from lOmg to lg of active substance per kg of seeds. Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.
  • the resultant resin was dissolved in ethylacetate (500ml) at a temperature of 50°C and the organic phase was washed twice with water. Drying of the ethylacetate phase over sodium sulfate and distilling off the solvent in a water jet vacuum gave the raw material, which was purified by flash chromatography over silica gel (eluant: hexane/methylene chloride 7:1).
  • hydroxylamine hydrochloride (0.35g; 0.0048mol), sodium acetate (0.53g; 0.0064mol) and absolute methanol (30ml) were stirred at room temperature for about 15minutes. Then a solution of benzhydrilidene (2-bicyclopropyl- 2-yl-phenyl)amine (0.9g; 0.00267 mol) in methanol (15ml) was added dropwise. The resultant mixture was stirred for lhour at room temperature. After dilution with ethylacetate (250ml), the organic phase was washed twice with water.
  • BIOLOGICAL EXAMPLES FUNGICTDAL ACTIONS
  • Example B-l Action against Puccinia recondita /wheat (Brownrust on wheat)
  • Example B-2 Action against Podosphaera leucot ⁇ cha I apple (Powdery mildew on apple)
  • Example B-3 Action against Venturia inaequalis I apple (Scab on apple) 4 week old apple seedlings cv. Mclntosh are treated with the formulated test compound (0.02% active ingredient) in a spray chamber.
  • One day after application apple plants are inoculated by spraying a spore suspension (4xl0 5 conidia/ml) on the test plants. After an incubation period of 4 days at 21°C and 95%r.h. the plants are placed for 4 days at 21°C and 60%r.h. in a greenhouse. After another 4 day incubation period at 21°C and 95%r.h. the disease incidence is assessed.
  • Example B-4 Action against Erysiphe graminis I barley (Powdery mildew on barley)
  • Example B-5 Action against Botrytis cinerea I apple (Botrvtis on apple fruits)
  • Example B-9 Action against Septoria nodorum/ wheat (Septoria leaf spot on wheat) 1 week old wheat plants cv. Arina are treated with the formulated test compound (0.02% active ingredient) in a spray chamber.
  • a spore suspension (5xl0 5 conidia/ml) on the test plants.

Abstract

A compound of formula (I): F1 Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by groups R4, R5 and R6; R1 is hydrogen or halo; R2 is hydrogen or halo; R3 is optionally substituted C2-12 alkyl, optionally substituted C2-12 alkenyl, optionally substituted C2-12 alkynyl, optionally substituted C3-12 cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclyl; and R4, R5 and R6 are, independently, selected from hydrogen, halo, cyano, nitro, C1-4 haloalkyl, C1-4 alkoxyl (C(1-4) alkoxyl (C1-4) alkyl and C1-4 haloalkoxy (C1-4) alkyl, provided that at least one of R4, R5 and R6 is not hydrogen. The compounds of formula (I) have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms.

Description

0-CYCLOPROPY -CA BOXANILIDES AND THEIR USE AS FUNGICIDES
The present invention relates to novel ortho-substituted-cyclopropyl-azol- carboxamides which have microbiocidal activity, in particular fungicidal activity. The invention also relates to the preparation of these compounds, to novel intermediates used in the preparation of these compounds, to agrochemical compositions which comprise at least one of the novel compounds as active ingredient, to the preparation of the compositions mentioned and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.
EP0545099A2, JP06220035 and JP02129171 disclose certain ortho-unsubstituted- cyclopropyl-azol-carboxamides
The present invention provides a compound of formula (I):
Figure imgf000002_0001
Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by groups R4, R5 and R6; R1 is hydrogen or halo; R2 is hydrogen or halo; R3 is optionally substituted C2.12 alkyl, optionally substituted C2-ι2 alkenyl, optionally substituted C2.12 alkynyl, optionally substituted C3.j2 cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclyl; and R4, R5 and R6 are, independently, selected from hydrogen, halo, cyano, nitro, C 1. lkyl, Cj.4haloalkyl, Cι.4alkoxy(C1.4)alkyl and C haloalkoxy(Cι_4)alkyl, provided that at least one of R4, R5 and R6 is not hydrogen. Halo is fluoro, chloro or bromo.
Each alkyl moiety is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, wø-propyl, n-butyl, sec-butyl, wσ-butyl, tert-butyl or neo-pentyl.
When present, each optional substituent on an alkyl moiety is, independently, selected from halo, hydroxy, cyano, Cι.4alkoxyC(=O), formyl, nitro, Cι_4 alkoxy, CM haloalkoxy, C alkylthio, Cj.4 haloalkylthio, HC(OR')=N and R'R"NN=C(H); where R' and R" are, independently, hydrogen or C1.4 alkyl.
Alkenyl and alkynyl moieties can be in the form of straight or branched chains. The alkenyl moieties, where appropriate, can be of either the (E)- or (Z)-configuration. Examples are vinyl, allyl and propargyl.
When present, each optional substituent on alkenyl or on alkynyl is, independently, selected from those optional substituents given above for an alkyl moiety. Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. When present, each optional substituent on cycloalkyl is, independently, selected from Ci_3 alkyl and those optional substituents given above for an alkyl moiety.
The term heterocyclyl refers to a non-aromatic or aromatic ring containing up to 10 atoms including one or more (preferably one or two) heteroatoms selected, each independently, from O, S and N. Examples of such rings include 1,3-dioxolanyl, tetrahydrofuranyl, morpholinyl, thienyl and furyl. When present, each optional substituent on phenyl or on heterocyclyl is, independently, selected from
Figure imgf000003_0001
alkyl and those optional substituents given above for an alkyl moiety. When present, there are up to four optional substituents on phenyl, each independently selected.
When present, each optional substituent on an alkyl moiety is, independently, selected from the preferred list of halo, hydroxy, methoxy, trifluoromethoxy, difluoromethoxy, cyano and nitro.
When present, each optional substituent on alkenyl or on alkynyl is, independently, selected from the preferred list of halo and cyano.
When present, each optional substituent on cycloalkyl is, independently, selected from the preferred list of methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy and cyano.
When present, each optional substituent on phenyl or on a heterocyclyl group is, independently, selected from the preferred list of halo, hydroxy, methoxy, trifluoromethoxy, difluoromethoxy and cyano. It is prefeπed that Het is pyrrolyl, pyrazolyl, thiazolyl, pyridinyl, pyrimidinyl, thiophenyl, furyl, isothiazolyl or isoxazolyl (more preferably pyrrolyl, pyrazolyl or thiazolyl), each being substituted by groups R4, R5 and R6. Preferably R1 and R2 are, independently, hydrogen or fluoro.
Preferably R3 is C2-6 alkyl, optionally substituted C3.8 cycloalkyl, phenyl, thienyl or furyl.
Preferably R4, R5 and R6 are, independently, selected from hydrogen, halogen, CM alkyl, CM haloalkyl and Cι.4alkoxy(Cι.4)alkyl; provided that at least one of R4, R5 and R6 is not hydrogen. More preferably R4, R5 and R6 are, independently, selected from hydrogen, halogen, methyl, Cj.2 haloalkyl and methoxymethyl; provided that at least one of R4, R5 and R6 is not hydrogen.
Compounds of formula (II):
Figure imgf000004_0001
where R3 is as defined above for a compound of formula (I), are also novel and are useful as intermediates in the preparation of compounds of formula (I).
Therefore, in another aspect the present invention provides a compound of formula (H) where R3 is as defined above for a compound of formula (I).
The compounds of formula (I) and of formula (U) may exist as different geometric or optical isomers or in different tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.
The compounds in Tables 1 to 6 below illustrate compounds of the invention.
Table 1 provides 22 compounds of formula (II) wherein R is as defined in Table
1.
Table 1
Figure imgf000004_0002
Figure imgf000005_0001
Table X represents Table 2 (when X is 2) and represents Table 3 (when X is 3).
Table X
Figure imgf000005_0002
Figure imgf000006_0001
Figure imgf000007_0001
Figure imgf000008_0003
Table 2 provides 80 compounds of formula (la):
Figure imgf000008_0001
wherein R , 11, n D5
Figure imgf000008_0002
R4 , R3 and R are as defined in Table 2. Table 3 provides 80 compounds of formula (lb):
Figure imgf000009_0001
wherein R\ Rz, R3, R4, R5 and R6 are as defined in Table 3.
Table 4 provides 50 compounds of formula (lc):
Figure imgf000009_0002
wherein R > 1', R TJf2,
Figure imgf000009_0003
R τj4* and R3 are as defined in Table 4.
Table 4
Figure imgf000009_0004
Figure imgf000010_0001
Figure imgf000011_0002
Table 5 provides 54 compounds of formula (Id):
Figure imgf000011_0001
wherein R ,ι , R , R and R are as defined in Table 5.
Table 5
Figure imgf000011_0003
Figure imgf000012_0001
Figure imgf000013_0002
Table 6 provides 45 compounds of formula (le):
Figure imgf000013_0001
wherein R1, R2, R3 and R4 are as defined in Table 6.
Table 6
Compound R1 R2 RJ R4 Number
Figure imgf000014_0001
Figure imgf000015_0001
Throughout this description, temperatures are given in degrees Celsius; "NMR" means nuclear magnetic resonance spectrum; MS stands for mass spectrum; and "%" is percent by weight, unless corresponding concentrations are indicated in other units. The following abbreviations are used throughout this description: m.p. = melting point b.p.= boiling point.
S = singlet br = broad d = doublet dd = doublet of doublets t = triplet q = quartet m = multiplet ppm = parts per million
Table 7 shows selected melting point and selected NMR data, all with CDC13 as the solvent (unless otherwise stated; if a mixture of solvents is present, this is indicated as, for example, (CDC13 / dό-DMSO)), (no attempt is made to list all characterising data in all cases) for compounds of Tables 1 to 6. Unless otherwise stated, the data relate to a cis/trans mixture of each compound; a compound number which ends with the letter 'c' relates only to its cis-isomer and a compound number which ends with the letter Y relates only to its trans-isomer.
Table 7
Figure imgf000016_0001
Figure imgf000017_0001
2.76t 107-108
2.77c 82-84
2.77t 109-111
2.78c 119-122
2.78t 96-97
3.5 74-78
3.17 61-65
3.23 92-96
3.33 -0.1-0.90/m/16H(cis and trans); 1.45/m/lH(trans); resin 1.79/m/lH(cis); 3.58/s/6H (cis and trans); 6.82-7.13/m/10H(cis and trans); 7.92/s/l (NH-trans); 8.03/dd/lH(trans); 8.10/s/lH(NH-cis); 8.19/dd lH (cis).
3.39 0.63-1.83/m/26H(cis and trans); 3.72/s/6H(cis and trans); resin 6.95-7.38/m/10H(cis and trans); 8.05/s/lH(NH-trans); 8.18/dd/lH(trans); 8.30/dd/lH(cis).
3.45 0.6-1.90/m/30H(cis and trans); 3.70/s/6H(cis and trans); resin 6.98-7.35/m/8H(cis and trans); 8.08/s(broad)/2H(cis and trans); 8.17/d2H(trans); 8.25/d 2H(cis).
3.66c 1.40/m/IH; 1.50-1.65/m lH; 2.37/m/lH, 2.50/m/lH; resin 3.73/s/3H; 6.60-6.70/m/5/H; 6.97/m/2H; 7.18/m/3H; 7.82/s/lH(NH); 8.02/d/lH.
3.66t 146-148
3.68c 1.40/m/IH; 1.57/m/lH; 2.40/m/2H; 3.72/s/3H; 6.68/d/2H; resin 6.90-7.08/m/4H; 7.18/m/3H; 7.80/s/lH; 8.02/d/lH.
3.68t 150-152 3.76 resin
3.80c 123-126
3.80t 94-96 4.10 69-74
4.12 resin
Figure imgf000019_0001
The compounds according to formula (I) may be prepared according to the following reaction schemes. Scheme 1A
A compound of formula (H) [where R3 is as defined above for a compound of formula (I)] may be prepared by a reaction sequence starting with a crossed-aldol condensation of benzaldehyde with a ketone of formula CH3C(O)R [where R is as defined above for a compound of formula (I)] in the presence of NaOH or KOH in a solvent (such as water or ethanol) and usually under reflux conditions or alternatively by reaction of benzaldehyde with a Wittig reagent under standard conditions. The resulting α.β-unsaturated ketone of formula (UI) [where R3 is as defined above for a compound of formula (I)]:
Figure imgf000020_0001
may then be converted into a compound of formula (IV) [where R3 is as defined above for a compound of formula (I)]:
Figure imgf000020_0002
by reacting first with hydrazine hydrate in ethanol under reflux conditions and then heating (in the range 150 to 250°C) in the presence of KOH (distilling off the solvent). After nitration with HNO3/H2θ or HNO3/acetic anhydride in a cooled vessel (in the range -30°C to 0°C), the resultant o/p-mixture of nitrobenzene of formula (V) [where R3 is as defined above for a compound of formula (I)]:
Figure imgf000020_0003
may then be separated and catalytically reduced (Pt/C/H2 or Ra-Ni/H2) in a solvent (such as methanol, ethanol or THF) at room temperature, to produce a crude o/p-mixture of a compound of formula (II), which may be further purified by standard techniques.
Alternatively, a compound of formula (II) [where R3 is as defined above for a compound of formula (I)] may be prepared by a process as illustrated by the following reaction sequence and which involves a Pd(H)-catalysed imination step. Scheme IB
Figure imgf000021_0001
A compound of formula (NHI) [where R3 is as defined above for a compound of formula (I)] is added to bromine and methanol at a temperature of 5-10°C, after which triphenylphosphine in a solvent [such as tetrahydrofuran] is added, to produce a compound of formula (IX) [where R is as defined above for a compound of formula (I)], which in turn is added to sodium hydride, in a solvent [such as DMSO], and then reacted with 2-bromobenzaldehyde or 2-iodobenzaldehyde to yield a compound of formula (X) [where R3 is as defined above for a compound of formula (I) and Hal is bromo or iodo]. The resultant compound of formula (X) is then mixed with hydrazine hydrate in a solvent [such as ethanol] and heated to reflux, after which potassium hydroxide is added and the resultant reaction mixture is maintained at 200-220°C for several hours. A standard extraction and purification procedure yields a compound of formula (XI) [where R is as defined above for a compound of formula (I) and Hal is bromo or iodo] which may then be converted to a compound of formula (H) by mixing with benzophenone imine, sodium tertiary butoxide, tris-dibenzylideneacetone- dipalladium (Pdjdbaj), racemic 2,2'-bis(diphenylphosphino)-l,l'-binaphthyl (BIΝAP) and a solvent [such as benzene or toluene] and heating at reflux temperature, typically for several hours, and adding the resultant [usually crude isolated] imine to a mixture of hydroxylamine hydrochloride, sodium acetate and a solvent [such as methanol]. The resultant mixture is stirred, preferably for about an hour at room temperature, after which a cis-/trans-mixture of a compound of formula (II) may be extracted and subsequent separation of the cis- and trans-isomers achieved by using flash chromatography.
In the above illustrated Pd-catalysed imination process, instead of the catalyst- ligand-system Pd-dbaj/BINAP, the system palladium diacetate/l,l'-bis(diphenyl- phosphino)ferrocene (dppf) could be used as an alternative.
Reaction scheme IB is novel and inventive, particularly the use of a Pd(II)-catalysed imination step. Therefore in a still further aspect the present invention provides a process for preparing a compound of formula (II), where R3 is as defined above, comprising at least one of the steps of reaction scheme IB; in particular a step using a Pd(II)catalysι-ligand-system [where the ligand is selected from a suitable sterically demanding phosphine (for example BINAP or dppf)] to react a compound of formula (XT) [where Hal is bromo or iodo; and R3 is as defined above] with benzophenone imine optionally in the presence of a base [such as sodium-tert- butanolate, potassium-tert-butananolate, sodium carbonate, potassium carbonate or cesium carbonate] to produce a compound of formula (XII) [where R3 is as defined above].
Examples of imination reactions with benzophenone imine are provided in the literature (Journal of Organometallic Chemistry, 1999, 576, 125-146 and Tetrahedron Lettersl997, 38, 6367-6370).
Scheme 2
The synthesis of an amine of formula (HA)
Figure imgf000022_0001
[where R3Λ is hydrogen or methyl] may be accomplished by a reaction sequence started by a Wittig reaction of o-nitrobenzaldehyde with an ylide [prepared from a cyclopropylmethlytriphenylphosphonium bromide in the presence of a strong base, such as NaH in a solvent such as DMSO, in the range 0-85°C]. The resulting E/Z-mixture of a compound of formula (VI)
Figure imgf000023_0001
[where R3A is hydrogen or methyl] may be converted to a compound of formula (VII)
Figure imgf000023_0002
by the application of the Simmons Smith reaction (Zn/Cu,CH2I2, ether as solvent) to the olefin group of the compound of formula (VI). The reduction of the nitro group of the corresponding compound of formula (VII) may be performed using the conditions described in Scheme 1, to produce a compound of formula (HA). Scheme 3
A compound of formula (I) may be prepared by reacting a compound of formula Het-C(=O)-R* [where R* is halogen, hydroxy or Cι_6 alkoxy, but preferably chloro] with a compound of formula (II) as prepared above in the presence of a base (such as triethylamine, Hunig base, sodium bicarbonate, sodium carbonate, potassium carbonate, pyridine or quinoline, but preferably triethylamine) and in a solvent (such as diethylether, TBME, THF, dichloromethane, chloroform, DMF or NMP) for between lOminutes and 48hours (preferably 12 to 24hours) and between 0°C and reflux
(preferably 20 to 25°C). When R* is hydroxy, a coupling agent [such as benzotriazol-1- yloxytris(dimethylamino) phosphoniumhexafluorophosphate, bis-(2-oxo-3- oxazolidinyl)-phosphinic acid chloride, N,N'-dicyclohexylcarbodiimide or 1,1'- carbonyl-diimidazole] may be used. Scheme 4
A compound of formula (IA)
Figure imgf000023_0003
[where R3Λ is hydrogen or methyl] may be prepared by the reduction of the nitro group of a compound of formula (VI) [where R3A is hydrogen or methyl] using standard conditions (for example, catalytic reduction or Bechamp-reduction) followed by amidation with an acid chloride to provide a compound of formula (VII) [where R3A is hydrogen or methyl]
Figure imgf000024_0001
which is subsequently used in a Simmons-Smith reaction (Zn/Cu,CH2I2, ether as solvent) to provide a compound of formula (IA).
Surprisingly, it has now been found that the novel compounds of formula (I) have, for practical purposes, a very advantageous spectrum of activities for protecting plants against diseases that are caused by fungi as well as by bacteria and viruses.
The compounds of formula (I) can be used in the agricultural sector and related fields of use as active ingredients for controlling plant pests. The novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous cultivated plants. The compounds of formula I can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
It is also possible to use compounds of formula (I) as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil. Furthermore the compounds according to present invention may be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management, etc. The compounds of formula (I) are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Altemaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia). Additionally, they are also effective against the Ascomycetes classes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and of the Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara). Outstanding activity has been observed against powdery mildew (Erysiphe spp.). Furthermore, the novel compounds of formula I are effective against phytopathogenic bacteria and viruses (e.g. against Xanthomonas spp, Pseudomonas spp, Erwinia amylovora as well as against the tobacco mosaic virus).
Within the scope of present invention, target crops to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals.
The compounds of formula (I) are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects. Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890. The compounds of formula (I) are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations which influence the growth of plants. They can also be selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
The compounds of formula (I) can be mixed with other fungicides, resulting in some cases in unexpected synergistic activities. Mixing components which are particularly preferred are azoles, such as azaconazole, BAY 14120, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imiben- conazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, pyrifenox, prochloraz, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole; pyrimidinyl carbinole, such as ancymidol, fenarimol, nuarimol; 2-amino-pyrimidines, such as bupirimate, dimethirimol, ethirimol; morpholines, such as dodemorph, fenpropidine, fenpropimorph, spiroxamine, tridemorph; anilinopyrimidines, such as cyprodinil, mepanipyrim, pyrimethanil; pyrroles, such as fenpiclonil, fludioxonil; phenylamides, such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl; benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole, thiabendazole; dicarboximides, such as chlozolinate, dichlozoline, iprodione, myclozoline, procymidone, vinclozoline; carboxamides, such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, thifluzamide; guanidines, such as guazatine, dodine, iminoctadine; strobilurines, such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129, trifloxystrobin, picoxystrobin, BAS 500F (proposed name pyraclostrobin), BAS 520; dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram; N- halomethylthiotetrahydrophthalimides, such as captafol, captan, dichlofluanid, fluoromides, folpet, tolyfluanid; Cu-compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper, oxine-copper; nitrophenol-derivatives, such as dinocap, nitrothal-isopropyl; organo-p-derivatives, such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos, tolclofos-methyl; various others, such as acibenzolar-S-methyl, anilazine, benthiavalicarb, blasticidin-S, chinomethionate, chloroneb, chlorothalonil, cyflufenamid, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, SYP-LI90 (proposed name: flumorph), dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, fentin, ferimzone, fluazinam, flusulfamide, fenhexamid, fosetyl-aluminium, hymexazol, iprovalicarb, IKF-916 (cyazofamid), kasugamycin, methasulfocarb, metrafenone, nicobifen, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, sulfur, triazoxide, tricyclazole, triforine, validamycin, zoxamide (RH7281). A preferred method of applying a compound of formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen. However, the compounds of formula I can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula I may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation. A formulation [that is, a composition containing the compound of formula (I)] and, if desired, a solid or liquid adjuvant, is prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
The agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula I, 99.9 to 1 % by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant. Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from lOg to 1kg a.iVha, most preferably from 20g to 600g a.i./ha. When used as seed drenching agent, convenient dosages are from lOmg to lg of active substance per kg of seeds. Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.
The following non-limiting Examples illustrate the above-described invention in more detail.
EXAMPLE 1 This Example illustrates the preparation of Compound No. 1.5.
To a mixture of 17.4g (O.lmol) (2-isobutyl-cyclopropyl)benzene and 80ml of acetic acid anhydride was added a solution of 6.0g (0.095mol) nitric acid and 40ml acetic acid anhydride in such a manner that the internal temperature was kept constant at -30°C. The resulting reaction mixture was stirred for lhour at -30°C and then for 2hours at 0°C. Then the mixture was poured onto 500ml of ice water and extracted three times with hexane. The hexane phases were combined and twice washed with 5% aqueous bicarbonate solution. After drying of the organic phase over sodium sulphate and distilling off the solvent in a water jet vacuum, the crude reaction product was obtained. Purification by flash chromatography over silica get (eluant: ethylacetate/hexane 1:10) yielded 10.5g of a yellow oil (mixture of para- and ortho-nitroisomers) which was directly used in the next step. This isomeric mixture [consisting of 10.5g (0.048mol) 1 -(2-isobutyl-cycloproply)2-nitrobenzene and 1 -(2-isobutyl-cyclopropyl)-4- nitrobenzene] was dissolved in 110ml of ethanol and hydrogenated over 5%Pt/C catalyst for 45minutes. After the theoretical uptake of hydrogen had occurred, the catalyst was filtered off and the solvent was removed in vacuo. The crude isomeric aniline mixture was purified by flash chromatography (eluant: ethylacetate/hexane 1:2).
Yield: 6.38g of 2-(2-isobutyl-cyclopropyl)phenyl amine was obtained as a yellow oil (cis/trans mixture).
EXAMPLE 2 This Example illustrates the preparation of Compound 3.17.
A solution of 0.35g (O.OOlδmol) l-methyl-4-trifluoromethyl-pyrrole-3-carboxylic acid and 0.24g (0.0019mol) oxalylchloride in 15ml methylenechloride was stirred for 3hours at room temperature in the presence of two drops of absolute DMF. Then the acid chloride solution was slowly added to a solution of 0.34g (0.0018mol) 2-(2-isobutyl-cyclopropyl) phenylamine, 0.27g (0.0027mol) triethylamine and 10ml methylene chloride. The resulting mixture was then stirred for lόhours at room temperature. After removal of the solvent in vacuo, the crude material was taken up in ca. 100ml ethylacetate. The ethylacetate phase was twice washed with water and after drying the organic phase, the solvent was again distilled off in a water jet vacuum. The crude product was purified by flash chromatography (eluant: hexane/ethylacetate/methylene chloride 1:2:2). Yield: 0.52g 1 -methyl -4-trifluoromethyl-lH-pyrrole-3-carboxylic acid [2-(2- isobutyl-cyclopropyl)phenyl]amide in the form of a white powder (cis/trans-mixture).
EXAMPLE 3
This Example illustrates the preparation of Compound Nos. 1.10c and l.lOt. Step 1:
In a sulfonation flask, NaH (12.8g; 0.32mol) was added to absolute DMSO (600ml). After heating at 80°C for 90minutes, cyclopropylcarbonylmethyltriphenyl phosphoniumbromide (136.5g; 0.32mol) was added portionwise at room temperature. The resultant suspension was stirred for 30minutes at room temperature and then a solution of 2-bromobenzaldehyde (59.4g; 0.32mol) in absolute DMSO (100ml) was added dropwise. After heating the resultant mixture for 4hours at 50°C, the mixture was poured onto 2.51itres of ice water. Extraction with ethylacetate, drying over sodium sulfate and distilling off the solvent in a water jet vacuum yielded the crude product. Purification was achieved by vacuum distillation. Yield: 77.6g of E-3-(2-bromophenyl)-l-cyclopropylpropenone as a yellow oil
(b.p.: 125-130°C at 0.3mbar). Step 2:
In a sulfonation flask, a mixture of of E-3-(2-bromophenyl)-l-cyclo- propylpropenone (77.6g; 0.309mol) and hydrazine hydrate (23.2g; 0.464mol) in ethanol (25ml) was heated at reflux temperature for 2hours. Then powdered potassium hydroxide (85%) (24.4g; 0.37mol) was added and the excesses of hydrazine hydrate and solvent were distilled out of the flask. The remaining mixture was then heated at a temperature of 205-210°C for 3hours. The resultant resin was dissolved in ethylacetate (500ml) at a temperature of 50°C and the organic phase was washed twice with water. Drying of the ethylacetate phase over sodium sulfate and distilling off the solvent in a water jet vacuum gave the raw material, which was purified by flash chromatography over silica gel (eluant: hexane/methylene chloride 7:1).
Yield: 61.2g of 2-(2-bromophenyl)bicyclopropyl in the form of a slightly yellowish oil (cis/trans-mixture). Step 3:
A mixture of 2-(2-bromophenyl)bicyclopropyl (28.5g; 0.12mol), benzophenoneimine (26. lg; 0.144mol), sodium tertiary butoxide (16.1g; 0.168 mol), tris-dibenzyl-ideneacetonedipalladium (Pd-dba,) (0.43g; 0.474mmol), racemic 2,2'-bis(diphenylphosphino)l,l'-binaphthyl (BINAP) (0.83g; 1.34mmol) and absolute toluene (450ml) was heated at reflux temperature under an atmosphere of nitrogen for 6hours. Then the solvent was removed in a water jet vacuum and the residue was taken up in ethylacetate (750ml). The organic layer was washed three times with brine and then dried over sodium sulfate. After evaporation of the solvent, the crude product was obtained. Purification was achieved by using flash chromatography over silica gel (eluant: hexane/methylene chloride 5:1).
Yield: 39.9g of cis-/trans-mixture of benzhydrilidene (2-bi-cyclopropyl-2-yl- phenyl)amine in the form of a brownish oil. Step 4:
In a sulfonation flask, hydroxylamine hydrochloride (0.35g; 0.0048mol), sodium acetate (0.53g; 0.0064mol) and absolute methanol (30ml) were stirred at room temperature for about 15minutes. Then a solution of benzhydrilidene (2-bicyclopropyl- 2-yl-phenyl)amine (0.9g; 0.00267 mol) in methanol (15ml) was added dropwise. The resultant mixture was stirred for lhour at room temperature. After dilution with ethylacetate (250ml), the organic phase was washed twice with water. After drying the organic phase (sodium sulfate) and distilling off the solvent in a water jet vacuum, the crude product was obtained. The final purification and separation of the cis- and trans-isomers was achieved by using flash chromatography (eluant: hexane/ethylacetate 5:1). Yield: 0.21g of trans- and 0.15g of cis- 2-bicyclopropyl-2-yl-phenylamine in the form of brownish oils.
FORMULATION EXAMPLES FOR COMPOUNDS OF FORMULA (I) Working procedures for preparing formulations of the compounds of formula I such as Emulsifiable concentrates, Solutions, Granulates, Dusts and Wettable powders are described in WO 97/33890.
BIOLOGICAL EXAMPLES: FUNGICTDAL ACTIONS Example B-l: Action against Puccinia recondita /wheat (Brownrust on wheat)
1 week old wheat plants cv. Anna are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application wheat plants are inoculated by spraying a spore suspension (lxl05uredospores/ml) on the test plants. After an incubation period of 2 days at 20°C and 95% r. h. plants are kept in a greenhouse for 8days at 20°C and 60%r.h. The disease incidence is assessed lOdays after inoculation.
Compounds of Tables 2, 3, 4 and 5 show good activity in this test (<20% infestation). Infestation is prevented virtually completely (0-5% infestation) with each of compounds 2.5, 2.17, 2.18, 2.23, 2.24, 2.33, 2.45, 2.46t, 2.76c, 2.76t, 2.77c, 2.77t,3.5, 3.17, 3.23, 3.33, 3.45, 3.76, 4.10, 4.12, 4.26, 5.5, 5.12, 5.21c and 5.37c.
Example B-2: Action against Podosphaera leucotήcha I apple (Powdery mildew on apple)
5 week old apple seedlings cv. Mclntosh are treated with the formulated test compound (0.002% active ingredient) in a spray chamber. One day after application apple plants are inoculated by shaking plants infected with apple powdery mildew above the test plants. After an incubation period of 12 days at 22°C and 60%r.h. under a light regime of 14/10hours (light/dark) the disease incidence is assessed.
Compounds of Tables 2, 3 and 4 show good activity in this test. The compounds 2.5, 2.17, 2.18, 2.23, 2.24, 2.33, 2.45, 2.46t, 3.5, 3.17, 3.23, 3.33, 3.45, 4.10 and 4.12 each exhibit strong efficacy (<20% infestation).
Example B-3: Action against Venturia inaequalis I apple (Scab on apple) 4 week old apple seedlings cv. Mclntosh are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application apple plants are inoculated by spraying a spore suspension (4xl05conidia/ml) on the test plants. After an incubation period of 4 days at 21°C and 95%r.h. the plants are placed for 4 days at 21°C and 60%r.h. in a greenhouse. After another 4 day incubation period at 21°C and 95%r.h. the disease incidence is assessed.
Compounds of Tables 2 and 3 show good activity in this test. The compounds 2.5, 2.17, 2.18, 2.23, 2.24, 2.33, 2.45, 2.46t, 3.5, 3.17, 3.23, 3.33 and 3.45 each exhibit strong efficacy (<20% infestation).
Example B-4: Action against Erysiphe graminis I barley (Powdery mildew on barley)
1 week old barley plants cv. Express are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application barley plants are inoculated by shaking powdery mildew infected plants above the test plants. After an incubation period of 6 days at 20°C / 18°C (day/night) and 60%r. h. in a greenhouse the disease incidence is assessed.
Compounds of Tables 2, 3 and 4 show good activity in this test. The compounds 2.5, 2.17, 2.18, 2.23, 2.24, 2.45, 2.46t, 2.77c, 2.77t, 3.5, 3.17, 3.23, 3.45, 4.10 and 4.12 each exhibit strong efficacy (<20% infestation). Example B-5: Action against Botrytis cinerea I apple (Botrvtis on apple fruits)
In an apple fruit cv. Golden Delicious 3 holes are drilled and each filled with 30μl droplets of the formulated test compound (0.002% active ingredient). Two hours after application 50 μl of a spore suspension of B. cinerea (4xl05conidia/ml) are pipetted on the application sites. After an incubation period of 7 days at 22°C in a growth chamber the disease incidence is assessed.
Compounds of Tables 2, 3, 4, 5 and 6 show good activity in this test. The compounds 2.5, 2.17, 2.18, 2.23, 2.24, 2.33, 2.45, 2.46t, 2.76c, 2.76t, 2.77c, 2.77t, 3.5, 3.17, 3.23, 3.33, 3.76, 3.45, 3.76, 4.10, 4.12, 4.26, 5.5, 5.12, 5.21c and 5.37 each exhibit very strong efficacy (<10% infestation). Example B-6: Action against Botrytis cinerea I grape (Botrvtis on grapes)
5 week old grape seedlings cv. Gutedel are treated with the formulated test compound (0.002% active ingredient) in a spray chamber. Two days after application grape plants are inoculated by spraying a spore suspension (lxl06conidia ml) on the test plants. After an incubation period of 4 days at 21°C and 95%r.h. in a greenhouse the disease incidence is assessed.
Compounds of Tables 2, 3, 4, 5 and 6 show good activity in this test. The compounds 2.5, 2.17, 2.18, 2.23, 2.24, 2.45, 2.46t, 2.76c, 2.76t, 2.77c, 2.77t, 3.5, 3.17, 3.23, 3.33, 3.39, 3.76, 4.10, 4.12, 4.26, 5.5, 5.12, 5.21c and 5.37c each exhibit very strong efficacy (<10% infestation). Example B-7: Action against Botrytis cinerea I tomato (Botrvtis on tomatoes)
4 week old tomato plants cv. Roter Gnom are treated with the formulated test compound (0.002% active ingredient) in a spray chamber. Two days after application tomato plants are inoculated by spraying a spore suspension (lxl05conidia/ml) on the test plants. After an incubation period of 4 days at 20°C and 95%r.h. in a growth chamber the disease incidence is assessed.
Compounds of Tables 2, 3, 4, 5 and 6 show good activity in this test. The compounds 2.5, 2.17, 2.18, 2.23, 2.24, 2.33, 2.45, 2.46t, 2.76c, 2.76t, 2.77c, 2.77t, 3.5, 3.17, 3.23, 3.39, 3.45, 3.76, 4.10, 4.12, 4.26, 5.5, 5.12, 5.21c and 5.37c each exhibit very strong efficacy (<10% infestation). Example B-8: Action against Pyrenophora teres I barley (Net blotch on barley)
1 week old barley plants cv. Express are treated with the formulated test compound (0.002% active ingredient) in a spray chamber. Two days after application barley plants are inoculated by spraying a spore suspension (3xl04conidia/ml) on the test plants. After an incubation period of 2 days at 20°C and 95%r.h. plants are kept for 2 days at 20°C and 60%r.h. in a greenhouse. The disease incidence is assessed 4 days after inoculation. Compounds of Tables 2, 3, 4, 5 and 6 show good activity in this test. The compounds 2.5, 2.17, 2.18, 2.23, 2.24, 2.33, 2.45, 2.46t, 2.76c, 2.76t, 2.77c, 2.77t, 3.5, 3.17, 3.23, 3.39, 3.45, 3.76, 4.10, 4.12, 4.26, 5.5, 5.12, 5.21c and 5.37c each exhibit very strong efficacy (<20% infestation).
Example B-9: Action against Septoria nodorum/ wheat (Septoria leaf spot on wheat) 1 week old wheat plants cv. Arina are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application wheat plants are inoculated by spraying a spore suspension (5xl05conidia/ml) on the test plants. After an incubation period of 1 day at 20°C and 95%r.h. plants are kept for 10 days at 20°C and 60%r.h. in a greenhouse. The disease incidence is assessed 11 days after inoculation.
Compounds of Tables 2, 3 and 4 show good activity in this test. The compounds 2.5, 2.17, 2.18, 2.23, 2.24, 2.33, 2.45, 2.46t, 2.76c, 2.76t, 2.77c, 2.77t, 3.5, 3.17, 3.23, 3.33, 3.39, 3.45, 3.76, 4.10 and 4.12 each exhibit strong efficacy (<20% infestation).

Claims

1. A compound of formula (I):
Figure imgf000035_0001
Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by groups R4, R5 and R6; R1 is hydrogen or halo; R2 is hydrogen or halo; R3 is optionally substituted C2-ι2 alkyl, optionally substituted C2-12 alkenyl, optionally substituted C2.12 alkynyl, optionally substituted C3.12 cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclyl; and R4, R5 and R6 are, independently, selected from hydrogen, halo, cyano, nitro, CM alkyl,
CM haloalkyl, C].4alkoxy(Cι.4)alkyl and Cι.4haloalkoxy(Cι.4)alkyl, provided that at least one of R4, R5 and R6 is not hydrogen.
2. A compound of formula (I) as claimed in claim 1 where Het is pyrrolyl, pyrazolyl, thiazolyl, pyridinyl, pyrimidinyl, thiophenyl, furyl, isothiazolyl or isoxazolyl, each being substituted by groups R4, R5 and R6.
3. A compound of formula (I) as claimed in claim 1 or 2 where R1 is hydrogen or fluoro.
A compound of formula (I) as claimed in claim 1, 2 or 3 where R is hydrogen or fluoro.
5. A compound of formula (I) as claimed in claim 1, 2, 3 or 4 where R3 is C2-6 alkyl, optionally substituted C3.8 cycloalkyl, phenyl, thienyl or furyl.
6. A compound of formula (I) as claimed in claim 1, 2, 3, 4 or 5 where R4, R5 and R6 are, independently, selected from hydrogen, halogen, C alkyl, CM haloalkyl and CM alkoxy(Cι_4)alkyl; provided that at least one of R4, R5 and R6 is not hydrogen.
7. A compound of formula (H):
Figure imgf000036_0001
where R3 is as defined in claim 1 or 5.
8. A process for preparing a compound of formula (II) as claimed in claim 7 which comprises a step using a Pd(H)catalyst-ligand-system where the ligand is selected from a suitable sterically demanding phosphine to react a compound of formula (XI)
Figure imgf000036_0002
with benzophenone imine optionally in the presence of a base to produce a compound of formula (XH)
Figure imgf000036_0003
(XII)
where Hal is bromo or iodo; and R3 is as defined in claim 7.
9. A composition for controlling microorganisms and preventing attack and infestation of plants therewith, wherein the active ingredient is a compound of formula (I) as claimed in claim 1 together with a suitable carrier.
10. A method of controlling or preventing infestation of cultivated plants by phytopathogenic microorganisms by application of a compound of formula (I) as claimed in claim 1 to plants, to parts thereof or the locus thereof.
PCT/IB2003/000687 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and their use as fungicides WO2003074491A1 (en)

Priority Applications (17)

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BRPI0308230-0A BR0308230B1 (en) 2002-03-05 2003-02-21 O-cyclopropyl carboxanilide, composition and method of control or prevention of plant infestation by phytopathogenic microorganisms
DK03706779T DK1480955T3 (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and their use as fungicides
AU2003208490A AU2003208490B2 (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and their use as fungicides
DE60314600T DE60314600T2 (en) 2002-03-05 2003-02-21 O-CYCLOPROPYL-CARBOXANILIDES AND THEIR USE AS FUNGICIDES
US10/506,918 US7951752B2 (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and their use as fungicides
CA2477931A CA2477931C (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and their use as fungicides
EP03706779A EP1480955B1 (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and their use as fungicides
SI200330951T SI1480955T1 (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and their use as fungicides
IL16369203A IL163692A0 (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and their use as fungicides
MXPA04008314A MXPA04008314A (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and their use as fungicides.
KR1020047013715A KR100818540B1 (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilides and fungicidal composition comprising them
JP2003572960A JP4511191B2 (en) 2002-03-05 2003-02-21 O-cyclopropyl-carboxanilide and their use as fungicides
ZA2004/06395A ZA200406395B (en) 2002-03-05 2004-08-12 O-cyclopropyl-carboxanilides and their use as fungicides
HK05112077.6A HK1079785B (en) 2002-03-05 2005-12-29 O-cyclopropyl-carboxanilides and their use as fungicides
US12/420,440 US20090197925A1 (en) 2002-03-05 2009-04-08 O-cyclopropyl-carboxanilides and their use
FR12C0019C FR12C0019I2 (en) 2002-03-05 2012-03-20 O-CYCLOPROPYL-CARBOXANILIDES AND THEIR USE AS FUNGICIDES
NL350085C NL350085I2 (en) 2002-03-05 2017-12-29 Sedaxane

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