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WO1999023066A1 - Derives de dithiocarbazate et utilisation de ces derniers comme pesticides - Google Patents

Derives de dithiocarbazate et utilisation de ces derniers comme pesticides Download PDF

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Publication number
WO1999023066A1
WO1999023066A1 PCT/GB1998/003197 GB9803197W WO9923066A1 WO 1999023066 A1 WO1999023066 A1 WO 1999023066A1 GB 9803197 W GB9803197 W GB 9803197W WO 9923066 A1 WO9923066 A1 WO 9923066A1
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WO
WIPO (PCT)
Prior art keywords
compound
alkyl
arh
ppm
cdci3
Prior art date
Application number
PCT/GB1998/003197
Other languages
English (en)
Inventor
Geoffrey Gower Briggs
Clive Leonard Cornell
Darren James Mansfield
Richard Michael Turner
Original Assignee
Agrevo Uk Limited
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
Application filed by Agrevo Uk Limited filed Critical Agrevo Uk Limited
Priority to AU96353/98A priority Critical patent/AU9635398A/en
Publication of WO1999023066A1 publication Critical patent/WO1999023066A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C337/02—Compounds containing any of the groups, e.g. thiocarbazates
    • C07C337/04—Compounds containing any of the groups, e.g. thiocarbazates the other nitrogen atom being further doubly-bound to a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/56—Radicals substituted by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Definitions

  • This invention relates to compounds having pesticidal, especially fungicidai, insecticidal and acaricidal, activity.
  • the invention provides a compound of general formula I
  • W is methyl or methoxy
  • R1 and R which may be the same or different, are alkyl, alkenyl, alkynyl, carbocyciyi or heterocyclyl each of which may be substituted;
  • R2 and R 3 which may be the same or different, have the same meaning as R1 , or R ⁇ and R 3 together with the atoms to which they are attached form an optionally substituted 5- to 7-membered heterocyclyl group;
  • R4 is optionally substituted alkyl, (preferably unsubstituted alkyl having 1 to 5 carbon atoms);
  • R5 is alkyl, haloalkyi, alkenyl, alkynyl, cycloalkyl, halogen, cyano, nitro, alkoxy, alkylthio, haloalkoxy or optionally substituted phenyl; and q is 0 to 4 (preferably 0), wherein when q is 2, 3 or 4, each R 5 may be the same or different.
  • Any alkyl group present in the molecule may be straight or branched and is preferably of 1 to 10 carbon atoms, especially 1 to 7 and particularly 1 to 5 carbon atoms.
  • Any alkenyl or alkynyl group may be straight or branched and is preferably of 2 to 7 carbon atoms and may contain up to 3 double or triple bonds which may be conjugated, for example vinyl, allyl, butadienyl or propargyl.
  • carbocyciyi or carbocyclic includes, saturated carbocyciyi groups, preferably cyclopropane, cyciopentane or cyclohexane; unsaturated carbocyciyi groups having up to three double bonds, which may or may not be conjugated; and aromatic carbocyciyi groups, preferably phenyl.
  • Carbocyciyi groups are typically 3 to 8 membered rings.
  • carbocyciyi includes any fused combination of the aforementioned carbocyciyi groups, for example napthalene, phenanthrene, indane and indene.
  • heterocyclyl or heterocyclic includes both aromatic and non- aromatic heterocyclyl groups.
  • Heterocyclyl groups are generally 5, 6 or 7-membered rings containing up to 4 hetero atoms selected from nitrogen, oxygen and sulfur. Examples of heterocyclyl groups are furyl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, dioxolanyl, oxazolyl, thiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, dithianyl, thiomorpholino, pyridazinyl,
  • heterocyclyl includes fused heterocyclyl groups, for example benzimidazolyl, benzoxazolyl, imidazopyridinyl, benzoxazinyl, benzothiazinyl, oxazolopyridinyl, benzofuranyl, quinolinyl, quinazolinyl, quinoxalinyl, dihydroquinazolinyl, benzothiazolyl, phthalimido, benzofuranyl, benzodiazepinyl, indolyl and isoindolyl.
  • Any alkyl, alkenyl, alkynyl, carbocyciyi, heterocyclyl group, when substituted, may be substituted by at least one group, which may be the same or different, and may be selected from the group: nitro; halogen; cyano; acyl -O-acyl; -S-acyl; optionally substituted carbocyciyi; optionally substituted heterocyclyl; -SF5;
  • R a is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyciyi and optionally substituted heterocyclyl; -OR D and -SR D where R D is the same as R a or hydrogen; NR C R" where R c and R 0 " , which may be the same or different, are hydrogen, optionally substituted alkyl, acyl, or R c and R d taken together with the nitrogen to which they are attached form a heterocyclyl group, preferably a 5 to 7-membered heterocyclyl group, which may be substituted and may contain other hetero atoms, for example morphoiino, thiomorpholino or pipendinyl.
  • Any carbocyciyi or heterocyclyl groups may also be substituted by optionally substituted alkyl, optionally substituted alkenyl and optionally substituted alkynyl.
  • Particularly preferred substituents on any alkyl, alkenyl or alkynyl group are halogen, alkoxy, haloalkoxy, alkylthio or optionally substituted phenyl.
  • Particularly preferred substituents on any carbocyciyi or heterocyclyl group are as defined above for alkyl, alkenyl or alkynyl, and also alkyl and haloalkyi.
  • acyl includes the residue of sulfur and phosphorus-containing acids as well as carboxylic acids
  • Each crossed bond depicted in general formula I represents a double bond having either Z or E stereochemistry It is intended that the invention includes individual isomers as well as mixtures thereof
  • the double bond attached to W preferably has E stereochemistry
  • the invention includes individual tautomers as well as mixtures thereof
  • the invention includes individual isomers as well as mixtures thereof
  • R “1 and R 6 which may be the same or different, are alkyl or phenyl, each of which may be substituted Any alkyl group may be substituted independently by one or more alkenyl, alkynyl, cycloalkyl, halogen, cyano, nitro, alkoxy, alkylthio, haloalkoxy or optionally substituted phenyl groups (preferably halogen, haloalkyi or alkoxy). Any phenyl group may be substituted independently by one or more of the same groups defined for alkyl, or alkyl or haloalkyi (preferably alkyl, halogen, haloalkyi or alkoxy). It is particularly preferred that R 6 is an unsubstituted alkyl group having 1 to 5 carbon atoms.
  • R ⁇ and R 3 are optionally substituted alkyl.
  • preferred substituents are -OR ⁇ , SR D , NR c R d , acyl, or an optionally substituted carbocyclic or heterocyclyl group.
  • substituents are benzoyl or phenyl, each of which may be substituted by one or more alkyl, haloalkyi, alkenyl, alkynyl, cycloalkyl, halogen, nitro, cyano, alkoxy, alkylthio, haloalkoxy, or optionally substituted phenyl groups (especially alkyl, haloalkyi, halogen, alkoxy or phenyl).
  • R ⁇ is unsubstituted alkyl and R 3 is alkyl substituted by benzoyl or phenyl, each of which may be substituted by alkyl, haloalkyi, halogen or aikoxy or phenyl.
  • the compounds of the invention have activity as fungicides, especially against fungal diseases of plants, e.g. mildews and particularly barley powdery mildew (Erysiphe graminis) and vine downy mildew (Plasmopara viticola), rice blast ⁇ Pyricularia oryzae), cereal eyespot ⁇ Pseudocercosporella herpotrichoides), rice sheath blight (Pellicularia sasakii), grey mould .Botrytis cinerea), damping off (Rhizoctonia solani), wheat brown rust (Puccinia recondita), late tomato or potato blight (Phytophthora infestans), apple scab ⁇ Venturia inaequalis), glume blotch [Leptosphaeria nodorum).
  • Other fungi against which the compounds may be active include other powdery mildews, other rusts,- and general pathogens of Deuteromycete
  • the compounds of the invention also have insecticidal, acaricidal and nematicidal activity and are particularly useful in combating a variety of economically important insects, acarids and plant nematodes, including animal ectoparasites and especially Diptera, such as sheep blow-fly, Lucilia sericata, and house-flies, Musca domestica; Lepidoptera, including Plutella xylostella, Spodoptera littoralis, Heliothis armigera and Pieris brassicae Homoptera, including aphids such as Megoura viciae; Coleoptera, including corn rootworms .Diabrotica spp., e.g.
  • the invention thus also provides a method of combating pests (i.e. fungi, insects, nematodes and acarids) at a locus infested or liable to be infested therewith, which comprises applying to the locus a compound of formula I.
  • pests i.e. fungi, insects, nematodes and acarids
  • the invention also provides an agricultural composition
  • an agricultural composition comprising a compound of formula I in admixture with an agriculturally acceptable diluent or carrier.
  • composition of the invention may of course include more than one compound of the invention.
  • composition can comprise one or more additional active ingredients, for example compounds known to possess plant-growth regulant, herbicidal, fungicidal, insecticidal or acaricidal properties.
  • additional active ingredients for example compounds known to possess plant-growth regulant, herbicidal, fungicidal, insecticidal or acaricidal properties.
  • the compound of the invention can be used in sequence with the other active ingredient.
  • the diluent or carrier in the composition of the invention can be a solid or a liquid optionally in association with a surface-active agent, for example a dispersing agent, emulsifying agent or wetting agent.
  • Suitable surface-active agents include anionic compounds such as a carboxylate, for example a metal carboxylate of a long chain fatty acid; an N-acylsarcosinate; mono- or di-esters of phosphoric acid with fatty alcohol ethoxylates or salts of such esters; fatty alcohol sulfates such as sodium dodecyl sulfate, sodium octadecyl sulfate or sodium cetyl sulfate; ethoxylated fatty alcohol sulfates; ethoxylated alkylphenol sulfates; lignin sulfonates; petroleum sulfonates; alkyl-aryl sulfonates such as alkyl-benzene s
  • butyl-naphthalene sulfonate salts of sulfonated naphthalene-formaldehyde condensates; salts of sulfonated phenol-formaldehyde condensates; or more complex sulfonates such as the amide sulfonates, e.g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e.g. the sodium sulfonate of dioctyl succinate.
  • Nonionic agents include condensation products of fatty acid esters.
  • fatty alcohols fatty acid amides or fatty-alkyl- or alkenyl-substituted phenols with ethyiene oxide
  • fatty esters of polyhydric alcohol ethers e.g. sorbitan fatty acid esters, condensation products of such esters with ethyiene oxide, e.g. polyoxyethylene sorbitan fatty acid esters, block copolymers of ethyiene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5-decyne-4,7-diol, or ethoxylated acetylenic glycols.
  • a cationic surface-active agent examples include, for instance, an aliphatic mono-, di-, or polyamine as an acetate, naphthenate or oleate; an oxygen-containing amine such as an amine oxide or polyoxyethylene alkylamine; an amide-linked amine prepared by the condensation of a carboxylic acid with a di- or polyamine; or a quaternary ammonium salt.
  • compositions of the invention can take any form known in the art for the formulation of agrochemicals, for example, a solution, a dispersion, an aqueous emulsion, a dusting powder, a seed dressing, a fumigant, a smoke, a dispersible powder, an emulsifiable concentrate or granules. Moreover it can be in a suitable form for direct application or as a concentrate or primary composition which requires dilution with a suitable quantity of water or other diluent before application.
  • An emulsifiable concentrate comprises a compound of the invention dissolved in a water-immiscible solvent which is formed into an emulsion with water in the presence of an emulsifying agent.
  • a dusting powder comprises a compound of the invention intimately mixed and ground with a solid pulverulent diluent, for example, kaolin.
  • a granular solid comprises a compound of the invention associated with similar diluents to those which may be employed in dusting powders, but the mixture is granulated by known methods. Alternatively it comprises the active ingredient absorbed or adsorbed on a pre-granular diluent, for example, Fuller's earth, attapulgite or limestone grit. Wettable powders, granules or grains usually comprise the active ingredient in admixture with a suitable surfactant and an inert powder diluent such as china clay.
  • Another suitable concentrate is a flowable suspension concentrate which is formed by grinding the compound with water or other liquid, a wetting agent and a suspending agent.
  • the concentration of the active ingredient in the composition of the present invention, as applied to plants is preferably within the range of 0.0001 to 1 .0 per cent by weight, especially 0.0001 to 0.01 per cent by weight.
  • the amount of active ingredient can vary widely and can be, for example, from 5 to 95 per cent by weight of the composition.
  • the compound is generally applied to seeds, plants or their habitat.
  • the compound can be applied directly to the soil before, at or after drilling so that the presence of active compound in the soil can control the growth of fungi which may attack seeds.
  • the active compound can be applied in any manner which allows it to be intimately mixed with the soil such as by spraying, by broadcasting a solid form of granules, or by applying the active ingredient at the same time as drilling by inserting it in the same drill as the seeds.
  • a suitable application rate is within the range of from 5 to 1000 g per hectare, more preferably from 10 to 500 g per hectare.
  • the active compound can be applied directly to the plant by, for example, spraying or dusting either at the time when the fungus has begun to appear on the plant or before the appearance of fungus as a protective measure.
  • the preferred mode of application is by foliar spraying. It is generally important to obtain good control of fungi in the early stages of plant growth as this is the time when the plant can be most severely damaged.
  • the spray or dust can conveniently contain a pre- or post-emergence herbicide if this is thought necessary.
  • a suitable rate of application is from 0.025 to 5 kg per hectare, preferably from 0.05 to 1 kg per hectare.
  • the compounds of the invention can be applied to plants or parts thereof which have been genetically modified to exhibit a trait such as fungal and/or herbicidal resistance.
  • Compounds of general formula I i.e. compounds of formula la where X is oxygen, can be prepared from compounds of general formula II according to the following reaction scheme where Q a is a leaving group, preferably a halogen.
  • Choice of base is governed by the nature of R 3 and will be apparent to the skilled chemist.
  • R 3 is a benzylic group
  • a relatively weak base is preferred such as potassium carbonate in acetone solvent.
  • the preferred base is a metal hydride, such as sodium hydride, in tetrahydrofuran solvent.
  • Compounds of general formula II are themselves novel and accordingly the invention includes these compounds, where R 1 and R ⁇ are as defined above.
  • Compounds of formula II can be prepared by reacting compound of formula 111 with compound of formula IV. Preferred reaction conditions involve heating in methanol solvent.
  • Compounds of formula III can be prepared by reacting compound of formula V and compound of formula VI with potassium carbonate in acetone according to the following reaction scheme, where Q D is a leaving group, preferably halogen.
  • Compounds of general formula V can be prepared by methods known in the art. For instance, methods for preparing compounds of formula V, where W is methoxy, Y is CH, X is 0 and Q b is a halogen are given in EP 0 299 694; and where Y is N, X is 0 and Q b is a halogen, are given in EP 0 254 426.
  • compounds of general formula I can be prepared from other compounds of general formula I.
  • compounds of formula lb where X is NH can be prepared from compounds of formula la where X is 0, by treatment with NH2R ⁇ " amine, for example methylamine.
  • CH 3 C N, 2 x ArCH 3 ), 2.42 (3H, s, SMe), 3.85 (3H, br. s, OMe), 4.05 (3H, br. s, NOMe), 5.08 (2H, m, ArCH 2 0), 5.30 (1H, m, CHCH3), 7.18-7.50 (7H, m, ArH).
  • Pyricularia oryzae rice blast Leptosphaeria nodorum: glume blotch Plasmopara viticola: downy mildew of vines
  • Aqueous solutions or dispersions of the compounds at the desired concentration, including a wetting agent, were applied by spray or by drenching the stem base of the test plants, as appropriate. After a given time, plants or plant parts were inoculated with appropriate test pathogens and kept under controlled environmental conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the affected part of the plant was visually estimated. Compounds are assessed on a score of 1 to 3 where 1 is little or no control, 2 is moderate control and 3 is good to total control.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un composé selon la formule (I) dans laquelle X représente O ou NH; Y représente CH ou N; W représente méthyle ou méthoxy; R1 et R6 qui peuvent être semblables ou différents, sont de l'alkyle, alkényle, alkynyle, carbocyclyle ou hétérocyclyle pouvant être chacun substitué. R2 et R3 qui peuvent être semblables ou différents, présentent la même signification que R?1, ou R2 et R3¿ ensemble avec les atomes auxquels ils sont fixés, forment un groupe hétérocyclyle de 5 à 7 éléments, éventuellement, substitué. R4 est de l'alkyle éventuellement substitué. R5 est de l'alkyle, haloalkyle, alkényle, alkynyle, cycloalkyle, halogène, cyano, nitro, alcoxy, alkylthio, haloalcoxy ou du phényle éventuellement substitué; et q représente entre 0 et 4 où q représente 2, 3 ou 4. Chaque R5 peut être semblable ou différent.
PCT/GB1998/003197 1997-10-31 1998-10-27 Derives de dithiocarbazate et utilisation de ces derniers comme pesticides WO1999023066A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU96353/98A AU9635398A (en) 1997-10-31 1998-10-27 Dithiocarbazate derivatives and their use as pesticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9722893.6A GB9722893D0 (en) 1997-10-31 1997-10-31 Fungicides
GB9722893.6 1997-10-31

Publications (1)

Publication Number Publication Date
WO1999023066A1 true WO1999023066A1 (fr) 1999-05-14

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Application Number Title Priority Date Filing Date
PCT/GB1998/003197 WO1999023066A1 (fr) 1997-10-31 1998-10-27 Derives de dithiocarbazate et utilisation de ces derniers comme pesticides

Country Status (3)

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AU (1) AU9635398A (fr)
GB (1) GB9722893D0 (fr)
WO (1) WO1999023066A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009072837A2 (fr) 2007-12-06 2009-06-11 Kyung Nong Corporation Composés méthoxyimino et composition fongicide comprenant de tels composés
CN106431977A (zh) * 2015-08-12 2017-02-22 沈阳中化农药化工研发有限公司 一种不饱和肟醚类化合物及其用途

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0299694A2 (fr) * 1987-07-11 1989-01-18 AgrEvo UK Limited Acrylates fongicides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0299694A2 (fr) * 1987-07-11 1989-01-18 AgrEvo UK Limited Acrylates fongicides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009072837A2 (fr) 2007-12-06 2009-06-11 Kyung Nong Corporation Composés méthoxyimino et composition fongicide comprenant de tels composés
CN106431977A (zh) * 2015-08-12 2017-02-22 沈阳中化农药化工研发有限公司 一种不饱和肟醚类化合物及其用途

Also Published As

Publication number Publication date
GB9722893D0 (en) 1998-01-07
AU9635398A (en) 1999-05-24

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