IE871033L - Tetrahydrofuran-triazole or imidazole fungicides - Google Patents

Tetrahydrofuran-triazole or imidazole fungicides

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Publication number
IE871033L
IE871033L IE871033A IE103387A IE871033L IE 871033 L IE871033 L IE 871033L IE 871033 A IE871033 A IE 871033A IE 103387 A IE103387 A IE 103387A IE 871033 L IE871033 L IE 871033L
Authority
IE
Ireland
Prior art keywords
compound
formula
carbon atoms
group
alkyl
Prior art date
Application number
IE871033A
Other versions
IE61234B1 (en
Inventor
Alfred Greiner
Regis Pepin
Original Assignee
Rhone Poulenc Agrochimie
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR8606075A external-priority patent/FR2597868B1/en
Application filed by Rhone Poulenc Agrochimie filed Critical Rhone Poulenc Agrochimie
Publication of IE871033L publication Critical patent/IE871033L/en
Publication of IE61234B1 publication Critical patent/IE61234B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • C07D405/02—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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • 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
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
    • C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
    • C07C33/483—Monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • 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
    • C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with 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
    • C07D307/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Health & Medical Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)

Abstract

Compounds of formula: <IMAGE> Y is a halogen atom or a cyano or nitro group or an optionally halogenated alkyl or alkoxy group, n is a positive integer lower than 6 or zero, Tr denotes a 1,2,4-triazol-1-yl group and Im a 1,3-imidazol-1-yl group, R1 to R5 denote the halogen atom or a lower alkyl radical, X1 and X2 denote a halogen atom or a hydrocarbyl radical. Use of these compounds as fungicides especially against the disease of cereals and in arboriculture. [EP0246982A2]

Claims (9)

1. claims Compounds containing triasole or imidazole 10 15 20 25 tetrahydrofuran and phenyl groupscharacterised in that they correspond to the general formula (I) in which A is a group (¥) a«-Ph~ (CH2) , where Ph is a phsiwlene ring and m •- 0 or 1, Y is a halogen atom or a cyano or nitro group , or an optionally halogenated alkyl or alkoxy group, n is sero or a positive integer less than 6 , it being possible for the groups Y to be identical or different when n is greater than 1, Tr represents a 1,2,4-triazol-l-yl group and Im a 1,3~imidazol-1-yl group ^ to R5, which may be identical or different, represent a hydrogen atom or a linear or branched alkyl radical containing at most six carbon atoms, a cycloalkyl radical containing at most six carbon atoms, a phenyl or benzyl radical or an alkoxy radical containing at most six carbon atoims, it being possible for these various radicals to be optionally substituted with one or more halogen atoms or alkoxy radicals containing at most six carbon atoms; Xj and X2» which may be identical or different, represent a hydrogen atom,, a halogen atom,, an alkyl radical containing at most sis carbon atoHis^ a cycloalkyl radical containing at most six carbon atoms or a phenyl or benzyl radical, it being possible for these various radicals to be optionally substituted in a manner similar to the groups Rx to R3# Rs- - 40 - a group Q ™Rgi in which Q represents 0 or Sf and R6 represents a hydrogen atom or an alkyl radical containing at most six carbon atoms, a cycloalkyl radical containing at most six carbon atoms or a phenyl, bensyl? benzoyl or 5 acyl radical, it being possible for these radicals to be substituted in a manner similar to the groups R, to R5 and to have identical or different meanings when K1 and X2 each correspond to QR6 or SRg, a group of formula ~Q-R7-Q~, where Q has the same 10 meaning as above and in which R7 is a divalent hydrocarbon radieal comprising from 2 to 6 carbon atoms,, it being possible for one of these carbon atoms to be replaced by an oxygen or nitrogen atom,,, the said single divalent radical itself being optionally substituted with one or IS more halogen atoms or hydroxyl groups, .alkyl radicals containing at most six carbon atoms or alkoxy radicals containing at most six carbon atoms , a group -N-ReRg, in which R0 and Rs# which may be identical or different, represent a hydrogen atom or an 20 alkyl radical containing at most six carbon atoms, a cycloalkyl radical containing at most six carbon atoms or a phenyl radical, it being possible for these various radicals to be optionally substituted in a manner similar to the groups Rx to R34, or alternatively R8 and Rg together 25 can fiorxa a single divalent hydrocarbon radical comprising from 2 to 6 carbon atoms , it being possible for one of these carbon atoms to be replaced by an oxygen, sulphur or nitrogen atom, the said single divalent radical itself being optionally substituted with one or more halogen 30 atoms , hydroxyl groups, alkyl radicals containing at most six carbon atoms or optionally halogenated alkoxy radicals containing at most six carbon atoms, a group =N-R10, in which R10 corresponds to an alkyl radical containing at most six carbon atoms, or a 35 cycloalkyl radical containing at most is carbon atoms, or to a group of formula QEU in which Ru is an alkyl, it being possible for these radicals to be substituted in a" manner similar to the groups Rx to R5, or a hydroxyl group, a group M3 £! on condition that X2 is other than M3# Xj or X2 can correspond to =0 or =S, the other group being eliminated, on the general conditions that Xx and X2 cannot simultaneously correspond to a hydrogen atom or to an alkyl radical containing at most six carbon atoms, a, cycloalkyl radical containing at most six carbon atoms, a phenyl radical or a benzyl radical, and if and X2 are different and either one of them is QRS# then4, in this case only, Rs can be only a benzoyl or acyl group; and their salified forms.
2. Compounds according to Claim 1, characterised in that m = 0, n ■ 1, 2 or 3 and Y is a halogen atom.
3. Compounds according to Claims 1 and 2, characterised in that n = 1 or 2 and Y is a halogen atom in the ortho and/or para position.
4. Compounds according to Claim 3, characterised in that Y is a chlorine or bromine atom.
5. Triazole compounds according to one of Claims 1 to 4, characterised in that they correspond to the formula II in which Y, m and n have one of the meanings indicated in the compound of formula I, Rx to Es correspond to a hydrogen atom or to est alkyl or cycloalkyl group contain- ing at Most six carbon atoms,,, Hal corresponds to a halogen atom and Z, is .a halogen or hydrogen atom.
6. Compounds according to Claim 5, characterised in that Hal is chlorine or bromine and Xx is chlorine or bromine. - 42 -
7. Triazole compounds according to one of Claims 1 10 15 20 to 4, characterised in that they correspond to the formula III in which xe n and m have one of the meanings indicated in the compound of the formula I, Rx to R5 correspond to a hydrogen atom or to an alkyl or cycloalkyl group containing at most six carbon atomsf 1, corresponds to a hydrogen atom or to an alkyl or cycloalkyl group containing at most six carbon atoms, Q has the same meaning as in the formula I and Rg corresponds to a hydrogen atom or to an alkyl or cycloalkyl group containing at most six carbon atoms. 8 - Compounds according to Claim 7f characterised in that the groups Rx to R5 correspond to a hydrogen atom or to an alkyl or cycloalkyl group containing at most six carbon atoms, and R6 corresponds to an alkyl or cycloalkyl group containing at most six carbon atoms and optionally substituted in a manner similar to the groups HI to R5 • 9 - Process for the preparation of the compounds of formula 111, in which Rx to R3l, At? Tf n and Xj have the same meaning as in Claim 1 and Hal corresponds to a halogen atom, characterised in that it consists of the following steps: Step A halo ketone of formula Ila, C3> Rs or o R c lla - 43 - in which Y, n and R3 have th® same meaning as that given for the compounds of formula I and Z corresponds to a halogen atom, is reacted with an organometallic compound of formula lib. lib to obtain the compound of formula lie, on A *4, Rc (I A ft a. r4 H. lie Step hi The compound of formula lie is then reacted with an unsubstituted imidazole or triazole in the presence of an organic or inorganic bass and in a suitable solvent, Step c\ A halogen molecule or mixed halogen molecule is added to the compound IId in an inert solvent, leading to th© compound He# - 44 - Step The compound II is obtained by cyclisation of the compound He in the presence of an organic or inorganic base. 10. Process for the preparation of the compounds of formula llf in which Ej to Ra, y, n, A and. I, have the same meaning as in Claim 1 and Hal corresponds to a halogen atom, characterised in that a halogen molecule or mixed halogen molecule is added in an inert solvent to the compound lie according to Claim 9, to obtain the compound. Hf, Ilf the latter being cyclised in the presence of an organic or inorganic base to lead to the compound IIgt, to which an unsubstituted triazole or imidazole group is attached in the presence of an organic or inorganic base and in a suitable solvent. 11. Process for the preparation of the compounds of formula III or V, . ^4= or z-, III or r- in which Rx to Ra, Y, n, A and X! have the same meaning as in Claim 1 and Q corresponds to an oxygen or sulphur atom, characterised in that a compound of formula II or Ilg is reacted with a nucleophile containing a hetero atome of formula R5~Q~E in which R6 and Q have the saae meaning as in the compound of formula I and E is a cation^ in the presence of a bass and optionally of a phase transfer catalyst f and in the case where the starting material is the compound IIgf an unsubstituted imidazole or tria^ol® is attached., 12. Process for the preparation of the compounds of formula III in which Eg is an optionally mono- or poly-halogenated alkyl group containing at most six carbon atoms,, characterised in that a compound of formula III or Ilia in which Rg corresponds to a hydrogen atom is reacted with an alkyl halide (where appropriate mono- or poly-halogenated) in the presence of an organic or inorganic base, and in that an imidazole or triazole ring is then attached if the starting material is the compound Ilia in which H, to n, Y and A have the same meaning as in Claim 1 in which and 2, together correspond to an oxygen atom, characterised in that a compound of formula III or ' Ilia in which Y, a and R% to Rj have the same-meaning as in Claim 1 and 1 is a halogen atoa, and in Ilia or - 46 - which QRS corresponds to a hydroxyl group and Xx to a hydrogen acornt, is oxidised,, and in thatwhen the starting material is the compound lllat, an unsubstituted imidazole or triazole ring is then attached. 14. Process for the preparation of compounds of formula IV in which xl and X2 together correspond to a sulphur atom and Y, n and to R3 have the same meaning as in Claim 1, characterised in that the compound of the formula IV in which Si and X2 together correspond to an oxygen atom is subjected to a thionation. 15. Process for the preparation of the compounds of formula v, characterised in that the compounds of formula IV or IVa or ~r IV in which Xx and X2 together correspond to an oxygen or sulphur atom doubly bonded to the tetrahydrofuran are reacted with a compound of formula HQRSi, where Q corresponds to 0 or Sf in the presence of an acid catalyst and in a suitable solvent, which can be the alcohol or thiol itself or an inert solvent; if the starting material is the compound of formula IVa, the compound of formula Va is obtained, and an imidazole or triazole ring is then grafted onto the compound of formula Va. 16. Process for the preparation of the compounds of formula II in which Rj to RSf si, Y and A have the same meaning as in Claim 1 where and X2 correspond to a halogen atom, preferably chlorine or bromine, characterised in that a compound of formula III or Ilia in which Y, n, Rj, to Rs and A have the same meaning as in Claim 1 and Z is a halogen atom, and in which QB$ cor- -responds to a hydroxyl group and. Z, to a hydrogen atom, is A > -Js*- \ z. c / IVa - 47 - oxidised and in that phosphorous pentachloride is then added to the ketone (compound of formula. IV in which X, corresponds to an oxygen atom), optionally in the presence of an aprotic polar solvent and optionally of a quaternary ammonium halide, preferably at room temperature. 17. Compounds which can be used, where appropriate, as intermediates! in the preparation processes of Claims 9 to 16, characterised in that they correspond to the formulae Ilie and Ilie o M or -• A OH Q \ r. a. ^4 or h~k IIIc Hie in which Rx to RSt* Y, A, m, n, X, and S2 have any one of th© meanings stated in Claim 1 or
8. 18. Use of the compounds according to one of Claims 1 to 8 as a fungicide, in particular in the form of fungicidal compositions containing as active substance a compound according to one of Claims 1 to 8, preferably 0.5 to 95 % by weight, this active substance being in combination with at least one agriculturally acceptable inert carrier. 1
9. Process for the control of fungal diseases of crops, characterised in that an effective dose of an active substance according to one or Claims 1 to 8 is applied, preferably at a rate of 0.005 to 5 kg/ha, and advantageously 0.01 to 0.5 kg/ha. -48- 20. A compound as claimed is* Claim 1 „ substantially as hereinbefore described and exemplified. 21. A process for the preparation of a compound as claimed in Claim 1, substantially as hereinbefore described and exemplified. 22. A compound as claimed in Claim 1, whenever prepared by a process claimed in a preceding claim. 23. A process according to Claim 10 or 16 for the preparation of a compound of formula II given and defined therein, substantially as hereinbefore: described and exemplified. 24. A compound of formula II given and defined in Claim 10 or 16, whenever prepared by a process claimed in any one of Claims 10, 16 or 23. 25. A process according to Claim 11 for the preparation of a compound of the formula III or V given and defined therein, substantially as hereinbefore described and exemplified. 26. A compound of the formula III or V given and defined in Claim 11 whenever prepared by a process claimed in any one of Claims 11 or 25. 27. A process according to Claim 12 for the preparation of a compound of the formula III given and defined therein, substantially as hereinbefore described and exemplified. 28. A compound of the formula IIS given and defined in Claiss 12 whenever prepared by a process claimed in Claiss 12 or 27. -49- 29. A process according to Claim 13 'or-14 for th© preparation of a compound of the formula ' IV. given and defined therein, substantially as hereinbefore described and exemplified. '■ . 5 30, A compound of the formula IV given and defined irs Claim 13 or 14, whenever prepared by a process claimed in Claim 13, 14 or 29. 31. A process according to Claim 15 for the preparation of a compound of formula V given and defined therein^ 10 substantially as hereinbefore described and exemplified. 32. A compound of formula V given and defined in claim 15, whenever prepared by a process claimed in Claim 15 or 31. F. R. KELLY & CO.,, AGENTS FOR THE APPLICANTS.
IE103387A 1986-04-23 1987-04-22 Compounds containing triazole or imidazole groups and tetrahydrofuran, use of these as fungicides and processes for the preparation thereof IE61234B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8606075A FR2597868B1 (en) 1986-04-23 1986-04-23 COMPOUNDS WITH TRIAZOLE OR IMIDAZOLE AND TETRAHYDROFURANNE GROUPS, USE THEREOF AS FUNGICIDES AND METHODS OF PREPARATION
FR8703281A FR2611714A2 (en) 1986-04-23 1987-03-06 COMPOUNDS WITH TRIAZOLE OR IMIDAZOLE AND TETRAHYDROFURAN GROUPS, USE THEREOF AS FUNGICIDES AND METHODS OF PREPARATION

Publications (2)

Publication Number Publication Date
IE871033L true IE871033L (en) 1987-10-23
IE61234B1 IE61234B1 (en) 1994-10-19

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IE103387A IE61234B1 (en) 1986-04-23 1987-04-22 Compounds containing triazole or imidazole groups and tetrahydrofuran, use of these as fungicides and processes for the preparation thereof

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EP (1) EP0246982B1 (en)
JP (2) JPH0745497B2 (en)
KR (1) KR950011421B1 (en)
AR (1) AR244690A1 (en)
AT (1) ATE85335T1 (en)
AU (2) AU601973B2 (en)
BG (1) BG60841B1 (en)
BR (1) BR8701922A (en)
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DK (1) DK174326B1 (en)
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EG (1) EG18631A (en)
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FI (1) FI91866C (en)
FR (1) FR2611714A2 (en)
GR (1) GR3006994T3 (en)
HK (1) HK71196A (en)
HU (1) HU206587B (en)
IE (1) IE61234B1 (en)
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NL (1) NL971039I2 (en)
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ATE115577T1 (en) * 1987-11-20 1994-12-15 Schering Corp TRI- AND TETRA-SUBSTITUTED OXETANES AND TETRAHYDROFURANES AND THEIR INTERMEDIATE PRODUCTS.
GB8926981D0 (en) * 1988-12-23 1990-01-17 Ici Plc Heterocyclic derivatives
TW286264B (en) 1994-05-20 1996-09-21 Ciba Geigy Ag
KR20010052811A (en) * 1998-10-07 2001-06-25 미우라 아끼라 Mixtures of optical isomers of 1,2-disubstituted-2,3-epoxypropanes, process for producing the same, pesticides containing the same as the active ingredient and intermediates thereof
JP2001081353A (en) * 1999-07-13 2001-03-27 Nicca Chemical Co Ltd Aqueous liquid dye composition
WO2011101229A1 (en) 2010-02-22 2011-08-25 Syngenta Participations Ag Dihydrofuran derivatives as insecticidal compounds

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GB2115408B (en) * 1982-02-09 1985-10-16 Ici Plc Triazole and imidazole derivatives
GB8306512D0 (en) * 1983-03-09 1983-04-13 Ici Plc Heterocyclic compounds
FR2558834B1 (en) * 1984-01-26 1988-01-08 Rhone Poulenc Agrochimie FUNGICIDES WITH TRIAZOLE AND OLIGOETHER GROUPS

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PT84746A (en) 1987-05-01
EG18631A (en) 1993-08-30
OA08586A (en) 1988-11-30
AU7181787A (en) 1987-10-29
RO99432B1 (en) 1990-08-30
JPH0745497B2 (en) 1995-05-17
NL971039I2 (en) 1998-04-01
PL265327A1 (en) 1988-07-21
KR950011421B1 (en) 1995-10-04
ES2053576T3 (en) 1994-08-01
HUT44124A (en) 1988-02-29
EP0246982A3 (en) 1988-02-24
JPS62270578A (en) 1987-11-24
DZ1069A1 (en) 2004-09-13
DK203987A (en) 1987-10-24
AU616546B2 (en) 1991-10-31
BG79417A (en) 1993-12-24
FR2611714A2 (en) 1988-09-09
YU73487A (en) 1988-06-30
MA20949A1 (en) 1987-12-31
YU44624B (en) 1990-10-31
JPH0812608A (en) 1996-01-16
NO871634L (en) 1987-10-26
DK203987D0 (en) 1987-04-22
NO167459B (en) 1991-07-29
TNSN87057A1 (en) 1990-01-01
TR23491A (en) 1990-02-01
IE61234B1 (en) 1994-10-19
EP0246982A2 (en) 1987-11-25
FI91866C (en) 1994-08-25
ATE85335T1 (en) 1993-02-15
IL82271A0 (en) 1987-10-30
DK174326B1 (en) 2002-12-09
DE3783946T2 (en) 1993-06-03
BR8701922A (en) 1988-02-02
AU601973B2 (en) 1990-09-27
AU3923389A (en) 1989-11-16
PT84746B (en) 1989-12-29
FI871752A (en) 1987-10-24
HU206587B (en) 1992-12-28
BG60841B1 (en) 1996-05-31
FI91866B (en) 1994-05-13
IL82271A (en) 1992-03-29
NO871634D0 (en) 1987-04-21
HK71196A (en) 1996-05-03
GR3006994T3 (en) 1993-06-30
EP0246982B1 (en) 1993-02-03
CA1329612C (en) 1994-05-17
NL971039I1 (en) 1997-10-01
NZ220050A (en) 1990-09-26
MY102438A (en) 1992-06-30
KR870010046A (en) 1987-11-30
UA26370A (en) 1999-08-30
PL152618B1 (en) 1991-01-31
NO167459C (en) 1991-11-06
DE3783946D1 (en) 1993-03-18
AR244690A1 (en) 1993-11-30
FI871752A0 (en) 1987-04-22

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