LU83725A1 - SULPHIDIC ORGANIC COMPOUNDS AND THEIR USE AS ACARICIDES, INSECTICIDES AND / OR FUNGICIDES - Google Patents

SULPHIDIC ORGANIC COMPOUNDS AND THEIR USE AS ACARICIDES, INSECTICIDES AND / OR FUNGICIDES Download PDF

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LU83725A1
LU83725A1 LU83725A LU83725A LU83725A1 LU 83725 A1 LU83725 A1 LU 83725A1 LU 83725 A LU83725 A LU 83725A LU 83725 A LU83725 A LU 83725A LU 83725 A1 LU83725 A1 LU 83725A1
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active ingredient
composition according
insecticide
acaricide
new
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LU83725A
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French (fr)
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Jean Marie De Muylder
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Seresci
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Priority to LU83725A priority Critical patent/LU83725A1/en
Priority to AT82201292T priority patent/ATE17635T1/en
Priority to DE8282201292T priority patent/DE3268870D1/en
Priority to EP82201292A priority patent/EP0078562B1/en
Priority to CA000413813A priority patent/CA1173747A/en
Priority to AU89750/82A priority patent/AU8975082A/en
Publication of LU83725A1 publication Critical patent/LU83725A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids

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

Abstract

1. Acaricidal composition containing, as active ingredient, at least a sulphur-containing organic compound of the following formula I : see diagramm : EP0078562,P13,F1 in which R and R1 are different organic radicals, characterized in that R represents a radical selected among the methyl, ethyl, propyl, butyl, hexyl and heptyl radicals having a straight or branched chain, the possibly methoxylated phenyl radical and the furyl-2 radical, and R1 represents a radical selected among the octyl, dodecyl and hexadecyl radicals or a thioacylhexamethylene group of the following formula II : see diagramm : EP0078562,P13,F2 in which R2 is identical to R1 , with the proviso that R does not represent a phenyl radical, when R1 represents an octyl radical.

Description

La présente invention est relative à des composés organiques sulfurés et à leur utilisation en tant qu’acaricides, insecticides et/ou fongicides.The present invention relates to organic sulfur compounds and their use as acaricides, insecticides and / or fungicides.

L’invention concerne, en particulier des composés organiques sulfurés et des compositions utili- \ sables comme acaricides.agissant sur les sarcoptes, psorioptes, chorioptes, tiques, tétraniques et acares analogues tant souf forme d’oeufs que de larves et d’acares adultes, comme insecticides agissant sur les s poux, puces, pucerons et insectes nuisibles analogues et/ou comme fongicides agissant sur les tricophyton , microsporum et autres fongi nuisibles. Les compositions suivant l’invention sont ainsi utilisables non seulement en médecine vétérinaire, notamment pour le t traitement de la gale, de la pédiculose. et de la teigne, mais également en phytopharmacie, notamment pour lutter contre des araignées, telles que les tétraniques.The invention relates, in particular, to sulfur-containing organic compounds and to compositions which can be used as acaricides. Acting on sarcoptes, psorioptes, chorioptes, ticks, tetranus and similar acars both in the form of eggs and of larvae and acarids , as insecticides acting on lice, fleas, aphids and similar harmful insects and / or as fungicides acting on tricophyton, microsporum and other harmful fungi. The compositions according to the invention can thus be used not only in veterinary medicine, in particular for the treatment of scabies, pediculosis. and ringworm, but also in phytopharmacy, in particular to fight against spiders, such as tetranics.

La présente invention concerne tout d’abord de nouveaux composés répondant à la formule générale suivante : ΛThe present invention relates first of all to new compounds corresponding to the following general formula: Λ

XX

R - C—S - R<j (I) dans laquelle R désigne un radical choisi parmi les radicaux propyle, notamment n-propyle, isopropyle, butyle, % notamment tertiobutyle,heptyle, notamment n-heptyle, méthoxyphényle, furyle-2 ainsi que les radicaux de - formule : - (ch2)6 - s - c - r2, dans laquelle R^ désigne un radical propyle, notamment isopropyle, butyle, notamment tertiobutyle,phényle, 4 '< - 2 - I v vR - C — S - R <j (I) in which R denotes a radical chosen from the radicals propyl, in particular n-propyl, isopropyl, butyl,% in particular tert-butyl, heptyl, in particular n-heptyl, methoxyphenyl, furyl-2 as well that the radicals of - formula: - (ch2) 6 - s - c - r2, in which R ^ denotes a propyl radical, in particular isopropyl, butyl, in particular tert-butyl, phenyl, 4 '<- 2 - I vv

. ; I. ; I

• · ·,/ . ** ' '· ^*V »· . , ; 1 '^·,ν; v >·-·· » ' (ί i ^ · •’l * ’ · · * '*·'···· ................... , *»?,'. 1 méthoxyphényle et furyle-2, tandis que désigne un radical choisi parmi les radicaux octyle, dodécyle, hexadécyle, benzyle et cyclohexyle. t Plus particulièrement, l'invention concerne de nouveaux thioesters de formule R - C - S ~ R1 (n) dans laquelle R désigne un radical choisi parmi les radicaux propyle, notamment n-propyle et isopropyle, ' butyle, notamment tertiobutyle, heptyle, notamment n-heptyle, méthoxyphényle et furyle-2, tandis que R^ désigne un radical choisi parmi les radicaux octyle, dodécyle, hexadécyle, benzyle et cyclohexyle.• · ·, /. ** '' · ^ * V »·. ,; 1 '^ ·, ν; v> · - ·· "'(ί i ^ · •' l * '· · *' * · '···· ..................., * "?, '. 1 methoxyphenyl and furyl-2, while denotes a radical chosen from octyl, dodecyl, hexadecyl, benzyl and cyclohexyl. T More particularly, the invention relates to new thioesters of formula R - C - S ~ R1 (n) in which R denotes a radical chosen from the propyl radicals, in particular n-propyl and isopropyl, butyl, in particular tert-butyl, heptyl, in particular n-heptyl, methoxyphenyl and furyl-2, while R ^ denotes a radical chosen among the octyl, dodecyl, hexadecyl, benzyl and cyclohexyl radicals.

Parmi les nouveaux thioesters de formule II suivant l'invention, on peut citer en particulier ceux dans lesquelles R et R<j ont les significations indiquées dans le tableau I suivant ï TABLEAU I.Among the new thioesters of formula II according to the invention, mention may be made in particular of those in which R and R <j have the meanings indicated in Table I according to Table I.

N° de code R R^ 283 —n 12^25 284 —C^Hy—n “C16H33 292 -C^Hy-iso “C8H17 294 —C^Hy—iso ~6^33 1 302 (CH^j)^C- —CgH^y 303 (CH^)^C- "*^12^25 ‘ ' 304 (CH3)3C- ~c16H33 312 CyH^-n “C8H17 ; 314 CyH15-n rC16H33 319 c7H15-n -ch2-c6h5 . i .·*/·*RR code number ^ 283 —n 12 ^ 25 284 —C ^ Hy — n “C16H33 292 -C ^ Hy-iso“ C8H17 294 —C ^ Hy — iso ~ 6 ^ 33 1 302 (CH ^ j) ^ C - —CgH ^ y 303 (CH ^) ^ C- "* ^ 12 ^ 25 '' 304 (CH3) 3C- ~ c16H33 312 CyH ^ -n“ C8H17; 314 CyH15-n rC16H33 319 c7H15-n -ch2-c6h5 . i. · * / · *

Tableau X (suite)Table X (continued)

Ne de code RNo R code

261 -CH30-C6H5 -C8hi7' . ' 262 -CH^O-CgH^ cyclohexyle 263 "CH3“C6H5 “c12H25 269 -CH3-C6H5 -CH2-C6H5 251 furyle 2 cyclohexyle 254 furyle-2 ~C12H25 L'invention concerne aussi, à titre de nouveaux composés les dithioacylmercapto-1,6-hexanes de formule : Φ q R3 _ c^- S - (CH2)6 - s - R3 (III] dans lauqelle les symboles R3 désignent un radical choisi parmi les radicaux propyle, notamment isopropy] butyle, notamment tertiobutyle, phényle, méthoxyphény] et furyle-2.261 -CH30-C6H5 -C8hi7 '. '262 -CH ^ O-CgH ^ cyclohexyl 263 "CH3“ C6H5 “c12H25 269 -CH3-C6H5 -CH2-C6H5 251 furyle 2 cyclohexyle 254 furyle-2 ~ C12H25 The invention also relates, by way of new compounds, to the dithioacylmercapto- 1,6-hexanes of formula: Φ q R3 _ c ^ - S - (CH2) 6 - s - R3 (III] in which the symbols R3 denote a radical chosen from propyl radicals, in particular isopropy] butyl, in particular tert-butyl, phenyl, methoxypheny] and furyle-2.

La présente invention concerne aussi des compositions topiques par exemple sous forme liquide ou solide, notamment sous forme de liquide, à pulvéris» sous forme de shampooings, sous forme de solution ou sous forme dfonguent.The present invention also relates to topical compositions, for example in liquid or solid form, in particular in the form of a liquid, in spray form, in the form of shampoos, in the form of a solution or in the form of a funguent.

Les compositions suivant l'invention sont des compositions acaricides, insecticides et/ou fongi- ' cides, pouvant éventuellement remplir une ou plusieurs de ces trois fonctions, ces compositions contenant, à titre d'ingrédient actif, un composé organique sulfuré répondant à la formule « • R4 - c - s - r3 (IV) , dans laquelle R,, désigne un radical choisi parmi les les radicaux méthyle, propyle, notamment n-propyle ou isopropyle, butyle, notamment tertiobutyle, heptyle, phényle, méthoxyphényle, furyle-2, ainsi que les radicaux -(CE^g- S -SC - Rg , dans laquelle Rg désigne un radical choisi parmi les radicaux méthyle, propyle, notamment n-propyle et isopropyle, butyle, notamment tertiobutyle, heptyle, phényle, méthoxyphényle ou furyle-2, et désigne un radical choisi parmi les radicaux octyle, dodécyle, hexadécyle, benzyle et cyclohexyle.The compositions according to the invention are acaricide, insecticide and / or fungicide compositions, which can optionally fulfill one or more of these three functions, these compositions containing, as active ingredient, an organic sulfur compound corresponding to the formula "• R4 - c - s - r3 (IV), in which R ,, denotes a radical chosen from methyl, propyl, in particular n-propyl or isopropyl, butyl, in particular tert-butyl, heptyl, phenyl, methoxyphenyl, furyl- 2, as well as the radicals - (CE ^ g- S -SC - Rg, in which Rg denotes a radical chosen from the methyl, propyl, in particular n-propyl and isopropyl, butyl, in particular tertiobutyl, heptyl, phenyl, methoxyphenyl or furyl-2, and denotes a radical chosen from octyl, dodecyl, hexadecyl, benzyl and cyclohexyl radicals.

. Parmi les Ingrédients actifs peuvent être contenus, comme ingrédients actifs dans les compositions ! acaricides, insecticides et/ou fongicides suivant 1’ invention, ou peut être, en particulier, ceux dans lesquels R^, R^ et Rg ont les significations indiquées dans les tableaux II et III suivants : TABLEAU II.. Among the active ingredients can be contained, as active ingredients in the compositions! acaricides, insecticides and / or fungicides according to the invention, or may be, in particular, those in which R ^, R ^ and Rg have the meanings indicated in Tables II and III below: TABLE II.

N° de code R^ ^5 272 CH^ ”^8^17 273 CH3 "c12H25 274 CH3 “C16H33 279 CH3 -CH2-CgH5 282 C3Hy—n "”^8^17 > 283 C3Hy—n -C12^25 284 C3Hy-n ""^16^33 289 C3Hy—n —CHg—CgH^ 292 CjH^-iso "C8H17 293 C3H^—iso “^12^25 / - 5 - 'Code No. R ^ ^ 5 272 CH ^ ”^ 8 ^ 17 273 CH3" c12H25 274 CH3 “C16H33 279 CH3 -CH2-CgH5 282 C3Hy — n" ”^ 8 ^ 17> 283 C3Hy — n -C12 ^ 25 284 C3Hy-n "" ^ 16 ^ 33 289 C3Hy — n —CHg — CgH ^ 292 CjH ^ -iso "C8H17 293 C3H ^ —iso“ ^ 12 ^ 25 / - 5 - '

Tableau II (sulbe) JTable II (sulbe) J

N° de code 294 C3H7-iso “Cl6H3-3 · 299 C^Hy-iso -CH2-C6H5 302 (CH3)3C- -C8H17 303 (CH3)3C- ~C12H25 304 (CH3)3C- "c16H33 309 (ch3)3c- -ch2-c6h5 312 C7H13-n “C8H17 ' 313 C7H15~n "C12H25 314 C7H15~n ”C16H33 319 0?Η15-η -CH2-C6H3 240 -C6H5 C4H9 241 -<^6H5 cyclohexyle- 242 “c6H5 “C12H25 260 CH30-C6H5 C4Hg 261 CH30-C6H3 C8H17 262 CR^O-CgH^ Cyclohexyle 263 CH30-C6H3 C12H25 269 CH30~C6H5 -CH2-C6H3 250 Furyle .’2. C4H9 251 Furyle.2. Cyclohexyle 252 Furyle.2. C8H17 254 Furyle.2. C12H25 259 Furyle. 2. -CH2-C6H3 i - 6 - I ; ' fi TABLEAU III.Code No. 294 C3H7-iso “Cl6H3-3299 C ^ Hy-iso -CH2-C6H5 302 (CH3) 3C- -C8H17 303 (CH3) 3C- ~ C12H25 304 (CH3) 3C-" c16H33 309 (ch3 ) 3c- -ch2-c6h5 312 C7H13-n “C8H17 '313 C7H15 ~ n" C12H25 314 C7H15 ~ n ”C16H33 319 0? Η15-η -CH2-C6H3 240 -C6H5 C4H9 241 - <^ 6H5 cyclohexyle- 242“ c6 “C12H25 260 CH30-C6H5 C4Hg 261 CH30-C6H3 C8H17 262 CR ^ O-CgH ^ Cyclohexyle 263 CH30-C6H3 C12H25 269 CH30 ~ C6H5 -CH2-C6H3 250 Furyle .'2. C4H9 251 Furyle. 2. Cyclohexyle 252 Furyle. 2. C8H17 254 Furyle. 2. C12H25 259 Furyle. 2. -CH2-C6H3 i - 6 - I; 'fi TABLE III.

N° de code Rg — 275 -(CH2)6 - S - C - CH3 \ 285 —(CH2)g — S — C — C-^Hy <1- nCode number Rg - 275 - (CH2) 6 - S - C - CH3 \ 285 - (CH2) g - S - C - C- ^ Hy <1- n

°V° V

295 -(CH^g - S - C - C3H?-iso 305 -(CELjg - S - C - (CH3)3 315 -(CH2)6 - S - C?H15 \ 243 -(CH2)6 - S - C - CgH5 " \ 264 -(CH2)5 - S - C - CHjO - C6H15 α 253 -(CH2)6 - S Λ - π (furyle-2)295 - (CH ^ g - S - C - C3H? -Iso 305 - (CELjg - S - C - (CH3) 3 315 - (CH2) 6 - S - C? H15 \ 243 - (CH2) 6 - S - C - CgH5 "\ 264 - (CH2) 5 - S - C - CHjO - C6H15 α 253 - (CH2) 6 - S Λ - π (furyle-2)

q Les composés de formule générale I ou IIq The compounds of general formula I or II

(R _ £ _ s - R^) dans laquelle R et R^ ont les significations indiquées plus haut peuvent être obtenus par le procédé suivant.(R _ £ _ s - R ^) in which R and R ^ have the meanings indicated above can be obtained by the following process.

Dans un ballon rond équipé d’un réfrigérant ascendant, on mélange des qualités équimoléculaires d’un chlorure d’acide de formule R.- C - Cl, dans laquelle R a l’une ou l’autre des significations indiquées plus haut, et d’un thiol de formule R^-SH, dans laquelle R^ a l’une ou l’autre des significations indiquées plus haut.In a round flask equipped with an ascending cooler, equimolecular qualities of an acid chloride of formula R.- C - Cl are mixed, in which R has one or the other of the meanings indicated above, and of a thiol of formula R ^ -SH, in which R ^ has one or other of the meanings indicated above.

On porte peu à peu le mélange à la température de 130-140°C. Cette température est maintenue jusqu'à cessation du dégagement d'acide chlorhydrique gazeux (durée totale de la réaction : 4 H.) suivant la réaction : R-C + R»-SH + R — C " + HClThe mixture is gradually brought to the temperature of 130-140 ° C. This temperature is maintained until the evolution of gaseous hydrochloric acid is ceased (total reaction time: 4 hours) depending on the reaction: R-C + R "-SH + R - C" + HCl

Cl - R*Cl - R *

Le résidu est purifié soit par distillation sous pression réduite, soit par recristallisation dans l’alcool iso-propylique·The residue is purified either by distillation under reduced pressure or by recrystallization from isopropyl alcohol ·

Quant aux composés de formule générale III (R^ - C - S - (CH^)^ - S -u - R^), dans laquelle a l’une ou l’autre des significations indiquées plus haut, il peuvent être préparés par le procédé suivant :As for the compounds of general formula III (R ^ - C - S - (CH ^) ^ - S -u - R ^), in which has one or other of the meanings indicated above, they can be prepared by the following process:

Dans un ballon rond surmonté d’un réfrigérant ascendant, on mélange deux moles d’un chlorure d’acide de formule R^-C - Cl, dans laquelle R^ a l’une ou l’autre des significations indiquées plus haut, et une mole d’hexane-dithiol de formule HS - (C^)^ - SH.In a round flask surmounted by an ascending cooler, two moles of an acid chloride of formula R ^ -C - Cl are mixed, in which R ^ has one or other of the meanings indicated above, and one mole of hexane-dithiol of formula HS - (C ^) ^ - SH.

On porte le mélange peu à peu jusqu’à 130-140°C en maintenant cette température jusqu’à cessation du dégagement d’acide chlorhydrique suivant la réaction : .0 .0 n 2 R,-C + HS-(CËL)A-SH —+ Rx-C i U^C-R, 3 'Cl 2 6 3- ^-(CH^g-s' 3The mixture is gradually brought to 130-140 ° C while maintaining this temperature until cessation of the release of hydrochloric acid according to the reaction: .0 .0 n 2 R, -C + HS- (CËL) A -SH - + Rx-C i U ^ CR, 3 'Cl 2 6 3- ^ - (CH ^ gs' 3

Le produit de réaction est purifié soit par distillation sous pression réduite,soit par recristallisation dans l’alcool isopropylique.The reaction product is purified either by distillation under reduced pressure or by recrystallization from isopropyl alcohol.

Les rendements de ces réactions sont compris entre 85 et 95 %·The yields of these reactions are between 85 and 95% ·

Les constants physiques des composésThe physical constants of the compounds

_ r _ I_ r _ I

(point d’ébullition E et points de fusion F, ainsi que teneurs en soufre calculées et trouvées des composés préparés par les procédés décrits ci-dessus sont indiq dans le tableau IV suivant , dans lequel les indices apposés aux points d’ébullition indiquent les pression en millimètres de mercure auxquelles ces points d'ébul tion ont été mesurés : TABLEAU IV.(boiling point E and melting points F, as well as sulfur contents calculated and found of the compounds prepared by the methods described above are indicated in the following table IV, in which the indices affixed at the boiling points indicate the pressure in millimeters of mercury at which these boiling points were measured: TABLE IV.

N° Dénomination Point de fu- Teneur e: sion ou d’é- freN ° Denomination Point of content- Content:

bullition Trouvé. CFound bullition. VS

H -l ·|ΙΓ1Γ| r ' T---1 "n·'·!·" ...... " ” π i 1 r_l 'Γ'~*1ΓΓ·~ mm—m—rn**.. "IH -l · | ΙΓ1Γ | r 'T --- 1 "n ·' ·! ·" ...... "” π i 1 r_l 'Γ' ~ * 1ΓΓ · ~ mm — m — rn ** .. "I

272 Thioacétate d’octyle E^:122° 17,1 T272 Octyl thioacetate E ^: 122 ° 17.1 T

273 Thioacétate de dodécyle ^:102° · 13.25 1.273 Dodecyl thioacetate ^: 102 ° · 13.25 1.

274 Thioacétate d’hexadécyle F:2803-28°6 10.4 11 279 Thioacétate de benzyle E.^1230 19.7 1!274 Hexadecyl thioacetate F: 2803-28 ° 6 10.4 11 279 Benzyl thioacetate E. ^ 1230 19.7 1!

282 Thiobutyrate d’octyle Eq y 80° 14.6 V282 Octyl thiobutyrate Eq y 80 ° 14.6 V

283 Thiobutyrate de dodécyle Eq ^:130° 12.1 T283 Dodecyl thiobutyrate Eq ^: 130 ° 12.1 T

284 Thiobutyrate d’hexadécyle Eq ^:172° 10.0 ! 289 Thiobutyrate de benzyle Eq 16.3 1<284 Hexadecyl thiobutyrate Eq ^: 172 ° 10.0! 289 Benzyl thiobutyrate Eq 16.3 1 <

292 Œhioisobutyrate d’octyle Eq ^:7^° 14.7 1J292 Octyl octiobutyrate Eq ^: 7 ^ ° 14.7 1J

293 Tüoisobutyrate de dodécyle Eq ^:111° 11.8 .1* 294 Thioisobutyrate d'hexadécyle Eq ^ :152° 10.0 ί293 Tüoisobutyrate dodécyle Eq ^: 111 ° 11.8 .1 * 294 Thioisobutyrate hexadecyle Eq ^: 152 ° 10.0 ί

299 IhioisobutyraiB de benzyle Eq ^ :75° 16.6 K299 Benzyl IhioisobutyraiB Eq ^: 75 ° 16.6 K

- 302 Thiopivalate d’octyle : 108° 13.9 1: .·.·'.. ·· _ 303 Thiopivalate de dodécyle Eq ^:124° 11.4 11- 302 Octyl thiopivalate: 108 ° 13.9 1:. ·. · '.. ·· _ 303 Dodecyl thiopivalate Eq ^: 124 ° 11.4 11

. · ':[-) 304 Thiopivalate d’hexadécyle EQ ^:1570 9.4 S. · ': [-) 304 Hexadecyl thiopivalate EQ ^: 1570 9.4 S

v.'.': 309 Thiopivalate de benzyle EQ ^:76° 15.4 1i tv. '.': 309 Benzyl thiopivalate EQ ^: 76 ° 15.4 1i t

Tableau IV (suite) N° Dénomination Point de fu- Teneur de sou- sion ou d'é- fre.Table IV (continued) N ° Denomination Point of fu- sion or sulfur content.

bullition Trouvé.Calculé 312 Thio-octanoate d’octyle Eq ^:128° 11.5% 11.8% 313 Thio-octanoate de dodécyle Eq ^:159° 9.9 9.8 314 Thio-octanoate d’hexadécyle F:36°4-37° 8.55 8.3 319 Thio-octanoate de benzyle Eq ^:123° 12.9 12.7 . 240 Thiobenzoate de butyle E2:121° 16.3 16.5 241 Thiobenzoate de cyclohexyle EQ ^,:121° 14.4 14.6 242 Thiobenzoate de dodécyle EQ 2^:167° 10.2 10.5 260 p.Thioanisoate de butyle Eq ^:128° ' 14.1/' 14.3 261 p.Thioanisoate d’octyle Eq ^: 167e 11.1 11.4 262 p.Thioanisoate de cyclo- JF : 38°2 12.8 12.8 hexyle \eq ^:156° 263 p.Thioanisoate de dodécyle F : 31°1 9.4 9.5 269 p.Thioanisoate de benzyle F: 51°-51°5 12.6 12.4 250 Thiofuroate 2. de butyle E2: 107° 17.6 17.4 251 Thiofuroate 2. de cyclo- ]F : 47°9 15.4 15.3 - .Bullition Found. Calculated 312 Octyl thio-octanoate Eq ^: 128 ° 11.5% 11.8% 313 Dodecyl thio-octanoate Eq ^: 159 ° 9.9 9.8 314 Hexadecyl thio-octanoate F: 36 ° 4-37 ° 8.55 8.3 319 Benzyl thio-octanoate Eq ^: 123 ° 12.9 12.7. 240 Butyl thiobenzoate E2: 121 ° 16.3 16.5 241 Cyclohexyl thiobenzoate EQ ^ ,: 121 ° 14.4 14.6 242 Dodecyl thiobenzoate EQ 2 ^: 167 ° 10.2 10.5 260 p.Butyl thioanisoate Eq ^: 128 ° '14.1 /' 14.3 261 p.Thioanisoate de octyle Eq ^: 167e 11.1 11.4 262 p.Thioanisoate de cyclo- JF: 38 ° 2 12.8 12.8 hexyle \ eq ^: 156 ° 263 p.Thioanisoate de dodécyle F: 31 ° 1 9.4 9.5 269 p. Benzyl thioanisoate F: 51 ° -51 ° 5 12.6 12.4 250 Butyl thiofuroate E2: 107 ° 17.6 17.4 251 Cyclo] thiofuroate 2. F: 47 ° 9 15.4 15.3 -.

hexyle \Eq 104° 252 Thiofuroate 2. d’octyle EQ Q: 135° 13.2 13.3 254 Thiofuroate 2. de dodécyle \EQ 165° 10.5 10.8 ; F : 28°7 259 Thiofuroate de benzyle Eq ^:127° 14.4 14.7 275 Diacétylmercaptohexane Eq 98° 27.3 27.3% 285 Dibutyrylmercaptohexane Eq 51^39° 22.2 22.1 295 Diisobutyrylmercaptohexane Eq ^:136° 22.1 22.1 305 Dipivaloylmercaptohexane Eq ^:145° ; 20.0 20.1 f -10 - i , · V ' v-’ . ‘ *v *............... . " ...... *" ......' *·"“ 11hexyl \ Eq 104 ° 252 Thiofuroate 2. octyl EQ Q: 135 ° 13.2 13.3 254 Thiofuroate 2. dodecyl \ EQ 165 ° 10.5 10.8; F: 28 ° 7,259 Benzyl thiofuroate Eq ^: 127 ° 14.4 14.7 275 Diacetylmercaptohexane Eq 98 ° 27.3 27.3% 285 Dibutyrylmercaptohexane Eq 51 ^ 39 ° 22.2 22.1 295 Diisobutyrylmercaptohexane Eq ^: 136 ° 22.1x.1qip 20.0 20.1 f -10 - i, · V 'v- ’. ‘* V * ................ "...... *" ...... '* · "“ 11

Tableau IV (suite) N° Dénomination Point de fu- Teneur de sou- sion ou d’é- fre.Table IV (continued) N ° Denomination Point of fu- ture.

bullition Trouvé.Calculé 315 Dioctanoylpercaptohexane F : 39-39°1 15*7 15.9 243 Dibenzoylmercaptohexane F :51°8-52°4 18.2 17.9 264 Di.p.anisoylmercaptobexane F :86°8-87° 15.5 15.3 253 Difuroyl.2.mercaptohexane F : 108°5—109°1 18.7 18.9Bullition Found Calculated 315 Dioctanoylpercaptohexane F: 39-39 ° 1 15 * 7 15.9 243 Dibenzoylmercaptohexane F: 51 ° 8-52 ° 4 18.2 17.9 264 Di.p. anisoylmercaptobexane F: 86 ° 8-87 ° 15.5 15.3 253 Difuroyl.2 .mercaptohexane F: 108 ° 5—109 ° 1 18.7 18.9

Le tableau V suivant indique les densités et indices de réfraction de certains composés tombant dans le cadre de la présente invention.Table V below indicates the densities and refractive indices of certain compounds falling within the scope of the present invention.

TABLEAU V.TABLE V.

22 · 22 N° de code Densité D ^ Indice de réfraction n^ 272 0,905 1,4615 273 0,8719 1,4620 279 1,081 1,5606 282 0,8588 · 1,4625 283 0,8754 1,4632 284 0,8770 1,4642 289 1,0377 1,5426 292 0,8842 1,4592 293 0', 8760 1,4621 294 0,8666 1,4628 299 1,0317 1,5408 302 0,8803 1,4590 303 0,8709 1.4618 304 0,8664 1,4635 309 1,0195 1,531122 · 22 Code number Density D ^ Refractive index n ^ 272 0.905 1.4615 273 0.8719 1.4620 279 1.081 1.5606 282 0.8588 · 1.4625 283 0.8754 1.4632 284 0, 8770 1.4642 289 1.0377 1.5426 292 0.8842 1.4592 293 0 ', 8760 1.4621 294 0.8666 1.4628 299 1.0317 1.5408 302 0.8803 1.4590 303 0, 8709 1.4618 304 0.8664 1.4635 309 1.0195 1.5311

Tableau V (suite) , 22 ?? N° de code Densite Indice de réfraction n ^ 312 0,8772 1,4648 ' ' 313 0,8710 1,4656 319 0,9828 1,5195 240 1,0419 1,5525 241 1,0850 1,5707 242 0,9554 1,5175 260 1,0877 1,5669 261 1,0245 1,5435 250 1,0880 1.5347 à 26° 252 1,0153 1,517 259 1,1926 1,6061 ♦ * 275 1,0496 1,5075 285 1,0060 1,4970 295 0,9983 1,4946 305 0,9820 1,4905Table V (continued), 22 ?? Code number Densite Refractive index n ^ 312 0.8772 1.4648 '' 313 0.8710 1.4656 319 0.9828 1.5195 240 1.0419 1.5525 241 1.0850 1.5707 242 0, 9554 1.5175 260 1.0877 1.5669 261 1.0245 1.5435 250 1.0880 1.5347 at 26 ° 252 1.0153 1.517 259 1.1926 1.6061 ♦ * 275 1.0496 1.5075 285 1, 0060 1.4970 295 0.9983 1.4946 305 0.9820 1.4905

Les exemples suivants décrivent quelques compositions acaricides, insecticides et/ou fongicides suivant l’invention.The following examples describe some acaricide, insecticide and / or fungicide compositions according to the invention.

EXEMPLE 1.EXAMPLE 1.

Liquide à pulvériser (spray) % en poidsLiquid by spray (spray)% by weight

matière active de formule I, IIactive ingredient of formula I, II

III ou IV 25%III or IV 25%

Solvant (tel que xylène) ΊΛ%Solvent (such as xylene) ΊΛ%

Agent mouillant anionique (tel que dodécylbenzène sulfonate de sodium) ou non ionique (tel que fa ’l ÊÊ % en poids alcoyl-phénoxy-polyoxythylène- éthénol) 4%Anionic wetting agent (such as sodium dodecylbenzene sulfonate) or nonionic wetting agent (such as% by weight alkyl-phenoxy-polyoxythylene-ethenol) 4%

La solution peut être utilisée pour le traitement de bovins ou de porcs infestés d'acares.The solution can be used to treat cattle or pigs infested with mites.

EXEMPLE 2.EXAMPLE 2.

Shampooing.Shampoo.

% en poids% in weight

matière active de formule I, IIactive ingredient of formula I, II

III ou IV 25%III or IV 25%

Texapon (Henkel A.G. - Allemagne fédérale) 8%Texapon (Henkel A.G. - Federal Germany) 8%

Eau q.s. ad 100%Water q.s. ad 100%

Ce shampooing convient pour le traitement d’animaux domestiques, tels que chiens et chats, souffrant de gale.This shampoo is suitable for the treatment of pets, such as dogs and cats, suffering from scabies.

-EXEMPLE 5.- EXAMPLE 5.

Solution à tamponner ou frictionner.Buffer or rub solution.

matière active de formule I, IIactive ingredient of formula I, II

.III ou IV 2,5% huile de paraffine 97,5%.III or IV 2.5% paraffin oil 97.5%

Cette solution convient notamment pour le traitement de la gale auriculaire.This solution is particularly suitable for the treatment of ear mites.

EXEMPLE 4.EXAMPLE 4.

Onguent.Ointment.

matière active de formule I, IIactive ingredient of formula I, II

III ou IV 2,5% excipient pour onguent cétylique (alcool cétylique, lanoline et paraffine) 97,5% λ mm t *III or IV 2.5% excipient for cetyl ointment (cetyl alcohol, lanolin and paraffin) 97.5% λ mm t *

Claims (67)

1. A titre de nouveaux composés organiques sulfurés, les composés répondant à la formule générale suivante : R - C -S - R1 (I), dans laquelle R désigne ton radical choisi parmi les radicaux propyle, notamment n-propyle, isopropyle, butyle, notamment tertiobutyle, heptyle, notamment n-heptyle, méthoxyphényle, furyle-2 ainsi que les radicaux de formule : - (C^)^ - S - C - Rg , dans laquelle désigne un radical propyle, notamment isopropyle, butyle, notamment tertiobutyle, phényle, méthoxyphényle et furyle-2, tandis que R^ désigne un radical choisi parmi les radicaux octyle, dodécyle, hexadécyle, benzyle et cyclohexyle.1. As new organic sulfur compounds, the compounds corresponding to the following general formula: R - C -S - R1 (I), in which R denotes your radical chosen from propyl radicals, in particular n-propyl, isopropyl, butyl , in particular tert-butyl, heptyl, in particular n-heptyl, methoxyphenyl, furyl-2 as well as the radicals of formula: - (C ^) ^ - S - C - Rg, in which denotes a propyl radical, in particular isopropyl, butyl, in particular tert-butyl , phenyl, methoxyphenyl and furyl-2, while R ^ denotes a radical chosen from octyl, dodecyl, hexadecyl, benzyl and cyclohexyl radicals. 2. A titre de nouveaux composés organiques sul- . furés suivant la revendication 1, les composés de r _ C^- S - R1 (II) dans laquelle R désigne un radical choisi parmi les radicaux propyle, notamment n-propyle et isopropyle, butyle, notamment tertiobutyle, heptyle, notamment n-heptyle, méthoxyphényle et furyle-2, tandis que R^ désigne un radical choisi parmi les radicaux octyle, dodécyle, hexadécyle, benzyle et cycloxyle.2. As new sul- organic compounds. furés according to claim 1, the compounds of r _ C ^ - S - R1 (II) in which R denotes a radical chosen from the radicals propyl, in particular n-propyl and isopropyl, butyl, in particular tert-butyl, heptyl, in particular n-heptyl , methoxyphenyl and furyl-2, while R ^ denotes a radical chosen from octyl, dodecyl, hexadecyl, benzyl and cycloxyl radicals. 3. A titre de nouveau tbioester, le thioiso-butyrate de dodécyle.3. As a new tbioester, dodecyl thioiso-butyrate. . 4. A titre de nouveau thioester, le thioiso- butyrate d’hexadécyle.. 4. As a new thioester, hexadecyl thioiso-butyrate. 5. A titre de nouveau thioester, le thioiào-butyrate d’octyle.5. As a new thioester, octyl thioio-butyrate. 6. A titre de nouveau thioester, le thioiso-butyrate d’hexadécyle.6. As a new thioester, hexadecyl thioiso-butyrate. 7. A titre de nouveau thioester, le thiopivalate d’octyle.7. As a new thioester, octyl thiopivalate. 8. A titre de nouveau thioester, le thiopivalate de dodécyle.8. As a new thioester, dodecyl thiopivalate. 9. A titre de nouveau thioester, le thiopivalate d’hexadécyle.9. As a new thioester, hexadecyl thiopivalate. 10. A titre de nouveau thioester, le thio-octanoate d’octyle10. As a new thioester, octyl thio-octanoate 11. A titre de nouveau thioester, le thio-octanoate f çL'hexadécyle.11. As a new thioester, thio-octanoate f çL'hexadécyle. 12. A titre de nouveau thioester, le thio-octanoate de benzyle.12. As a new thioester, benzyl thio-octanoate. 13. A titre de nouveau thioester, le p-thioanisate - d'octyle13. As a new thioester, octyl p-thioanisate 14. A titre de nouveau thioester, le p-thioanisate de cyclohexyle.14. As a new thioester, cyclohexyl p-thioanisate. 15. A titre de nouveau thioester, le p-thioanisate de dodécyle.15. As a new thioester, dodecyl p-thioanisate. 16. A titre de nouveau thioester, le p-thioanisate de benzyle.16. As a new thioester, benzyl p-thioanisate. 17. A titre de nouveau thioester, le thiofuroate-2 de butyle. ;;17. As a new thioester, butyl thiofuroate-2. ;; 18. A titre de nouveau thioester, le thiofuroate-2 de dodécyle. *18. As a new thioester, dodecyl thiofuroate-2. * 19. I ..: ^ ·, ' Γ " '19. I ..: ^ ·, 'Γ "' 19. A titre de nouveaux composés suivant la revendication 1, les dithioacylmercapto-1,6-hexanes de formule : .0 Ck R3 - C - S - (CH2)6 - s - c - r3 (iii) dans laquelle les symboles R^ désignent un radical choisi parmi les radicaux propyle,notamment isopropyle, butyle, notamment tertiobutyle, phényle, méthoxyphényle et furyle-2. • - ......1 i !19. As new compounds according to claim 1, the 1,6-dithioacylmercapto-hexanes of formula: .0 Ck R3 - C - S - (CH2) 6 - s - c - r3 (iii) in which the symbols R ^ denote a radical chosen from propyl, in particular isopropyl, butyl, in particular tert-butyl, phenyl, methoxyphenyl and furyl-2 radicals. • - ...... 1 i! 20. A titre de nouveau dithioacylmercapto-1,6-hexane le diisobutyrylmercaptohexane..20. As new dithioacylmercapto-1,6-hexane diisobutyrylmercaptohexane .. 21. v A titre de nouveau dithioacylmercapto-1,6-hexane, le dipivaloylmercaptohexane.21. v As new dithioacylmercapto-1,6-hexane, dipivaloylmercaptohexane. 22. A titre de nouveau dithioacylmercapto-1,6-hexane, le dibenzoylmercaptohexane.22. As the new 1,6-dithioacylmercapto-hexane, dibenzoylmercaptohexane. 23. A titre de nouveau dithioacylmercapto-1,6-hexane, le di-p-anisoylmercaptohexane.23. As the new 1,6-dithioacylmercapto-hexane, di-p-anisoylmercaptohexane. 24. A titre de nouveau dithioacylmercapto-1,6-hexane, le di-furoyl-2-mercaptohexane.24. As a new dithioacylmercapto-1,6-hexane, di-furoyl-2-mercaptohexane. 25. Compositions acaricides, insecticides et/ou fongicides topiques.contenant comme ingrédient actif au moins un composé organique sulfuré répondant à la formule R^ - C - S - R^ (VI) , dans laquelle désigné un « radical choisi parmi les radicaux méthyle, propyle, no tamment n-propyle ou isopropyle, butyle, notamment tertio- butyle, heptyle, phényle, méthoxyphényle, furyle-2, ainsi CL que les radicaux -(CH,,) g - S - C - Rg , dans laquelle Rg désigne un radical choisi parmi les radicaux méthyle, propyle, notamment n-propyle et isopropyle, butyle, notamment tertiobutyle, heptyle, phényle, méthoxyphényle ou furyle-2, et R^ désigne un radical choisi parmi les radicaux octyle, dodécyle, hexadécyle, benzyle et i cyclohexyle. j25. Topical acaricide, insecticide and / or fungicide compositions. Containing as active ingredient at least one organic sulfur compound having the formula R ^ - C - S - R ^ (VI), in which designated a "radical chosen from methyl radicals , propyl, in particular n-propyl or isopropyl, butyl, in particular tert-butyl, heptyl, phenyl, methoxyphenyl, furyl-2, as well as CL and the radicals - (CH ,,) g - S - C - Rg, in which Rg denotes a radical chosen from methyl, propyl, in particular n-propyl and isopropyl, butyl, in particular tert-butyl, heptyl, phenyl, methoxyphenyl or furyl-2 radicals, and R ^ denotes a radical chosen from octyl, dodecyl, hexadecyl, benzyl radicals and i cyclohexyl. j - 26. Composition acaricide, insecticide et/ou ' fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thioacétate d’octyle. I26. The acaricidal, insecticidal and / or fungicidal composition according to claim 25, containing, as active ingredient, octyl thioacetate. I 27. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thioacétate de dodécyle. . i -16 - u i27. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient dodecyl thioacetate. . i -16 - u i 28. Composition acaricide, insecticide et/ fongicide suivant la revendication 25, contenant à t d'ingrédient actif du thioacétate d'hexadécyle.28. The acaricide, insecticide and / fungicide composition according to claim 25, containing at t of active ingredient hexadecyl thioacetate. 29. Composition acaricide, insecticide· et/ fongicide suivant la revendication 255 contenant à t d’ingrédient actif du thioacétate de benzyle.29. acaricide, insecticide · and / fungicide composition according to claim 255 containing at t of active ingredient benzyl thioacetate. 30. Composition acaricide, insecticide et/ fongicide suivant la revendication 25, contenant à t d'ingrédient actif du thiobutyrate d'octyle.30. acaricide, insecticide and / fungicide composition according to claim 25, containing at t of active ingredient octyl thiobutyrate. * 31. Composition acaricide, insecticide et/ fongicide suivant la revendication 25, contenant à t d'ingrédient actif du thiobutyrate de dodécyle.* 31. acaricide, insecticide and / fungicide composition according to claim 25, containing at t active ingredient dodecyl thiobutyrate. 32. Composition acaricide, insecticide et/ fongicide suivant la revendication 25, contenant à t: d'ingrédient actif du thiobutyrate d'hexadécyle.32. acaricide, insecticide and / fungicide composition according to claim 25, containing at t: active ingredient of hexadecyl thiobutyrate. 33. Composition acaricide, insecticide et/< fongicide suivant la revendication 25, contenant à t: d'ingrédient actif du thiobutyrate de benzyle.33. acaricide, insecticide and / <fungicide composition according to claim 25, containing at t: active ingredient of benzyl thiobutyrate. 34. Composition acaricide, insecticide et/c fongicide suivant la revendication 25, contenant à tj d'ingrédient actif du thioisobutyrate d'octyle. . '.'h34. acaricide, insecticide and / c fungicide composition according to claim 25, containing tj of active ingredient of octyl thioisobutyrate. . '.'h 35. Composition acaricide, insecticide et/c fongicide suivant la revendication 25, contenant à t3 d’ingrédient actif du thioisobutyrate de dodécyle.35. acaricide, insecticide and / c fungicide composition according to claim 25, containing at t3 of active ingredient dodecyl thioisobutyrate. • ·. ’ 36. Composition acaricide, insecticide et/c . Z '' ' - · fongicide suivant la revendication 25, contenant à ti ' /''· ‘. d'ingrédient actif du thioisobutyrate d'hexadécyle.• ·. '36. Miticide, insecticide and / c composition. Z '' '- · fungicide according to claim 25, containing ti' / '' · ‘. active ingredient of hexadecyl thioisobutyrate. 37. Composition acaricide, insectide et/ou . " fongicide suivant la revendication 25, contenant à ti ·''</'> f d'ingrédient actif du thioisobutyrate de benzyle.37. Miticide, insecticide and / or composition. "A fungicide according to claim 25 containing at least one of the active ingredient benzyl thioisobutyrate. 38. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thiopivalate d'octyle.38. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient octyl thiopivalate. 39. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thiopivalate de dodécyle.39. acaricidal, insecticidal and / or fungicidal composition according to claim 25, containing as active ingredient dodecyl thiopivalate. 40. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thiopivalate d'hexadécyle.40. acaricide, insecticide and / or fungicide composition according to claim 25, containing, as active ingredient, hexadecyl thiopivalate. * 41. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thiopivalate de benzyle.* 41. Acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient benzyl thiopivalate. 42. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thio-octanoate d’octyle.42. acaricidal, insecticidal and / or fungicidal composition according to claim 25, containing as active ingredient octyl thio-octanoate. 43. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thio-octanoate de dodécyle.43. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient dodecyl thio-octanoate. 44. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thio-octanoate d'hexadécyle.44. acaricidal, insecticidal and / or fungicidal composition according to claim 25, containing, as active ingredient, hexadecyl thio-octanoate. 45. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre Γ d'ingrédient actif du thio-octanoate de benzyle.45. acaricide, insecticide and / or fungicide composition according to claim 25, containing as Γ active ingredient benzyl thio-octanoate. 46. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thiobenzoate de butyle.46. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient butyl thiobenzoate. 47. Composition acaricide, insecticide et/ou ;V; fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thiobenzoate de cyclohexyle.47. Miticide, insecticide and / or; V composition; A fungicide according to claim 25, containing as active ingredient cyclohexyl thiobenzoate. 48. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thiobenzoate de dodécyle.:48. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient dodecyl thiobenzoate .: 49. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thioanisoate de Tbutyle.49. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient Tbutyl thioanisoate. 50. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thioanisoate d’octyle.50. Miticide, insecticide and / or fungicide composition according to claim 25, containing, as active ingredient, octyl thioanisoate. - 51. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thioanisoate de cyclohexyle.- 51. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient cyclohexyl thioanisoate. 52. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif .du thioanisoate de dodécyle.52. acaricidal, insecticidal and / or fungicidal composition according to claim 25, containing, as active ingredient, dodecyl thioanisoate. 53. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thioanisoate de benzyle.53. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient benzyl thioanisoate. 54. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thiofuroate 2. de butyle.54. acaricidal, insecticidal and / or fungicidal composition according to claim 25, containing, as active ingredient, butyl thiofuroate 2. 55· Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thiofuroate 2. de cyclohexyle.55 · acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient thiofuroate 2. of cyclohexyl. 56. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thiofuroate 2. d’octyle.56. acaricidal, insecticidal and / or fungicidal composition according to claim 25, containing, as active ingredient, octyl thiofuroate 2. 57. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du thiofuroate 2. de dodécyle.57. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient dodecyl thiofuroate 2. 58. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du thiofuroate 2. de benzyle.58. acaricidal, insecticidal and / or fungicidal composition according to claim 25, containing, as active ingredient, benzyl thiofuroate 2. 59. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif dudiacétylmercaptohexane.59. acaricidal, insecticidal and / or fungicidal composition according to claim 25, containing, as active ingredient, diacetylmercaptohexane. 60. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du dibutyrylmercaptohexane.60. Miticide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient dibutyrylmercaptohexane. 61. Composition acaricide, insecticide et/ou ; fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du diisobutyrylmercaptohexane.61. Miticide, insecticide and / or composition; A fungicide according to claim 25, containing as an active ingredient diisobutyrylmercaptohexane. 62. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif.du dipivaloylmercaptohexane·.62. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient. Dipivaloylmercaptohexane ·. 63. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du dioctanoylmercaptohexane.63. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient dioctanoylmercaptohexane. 64. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d'ingrédient actif du dibenzoylmercaptobexane.64. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient dibenzoylmercaptobexane. 65. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du di.p.anisoylmercaptohexane.65. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient di.p.anisoylmercaptohexane. 66. Composition acaricide, insecticide et/ou fongicide suivant la revendication 25, contenant à titre d’ingrédient actif du difuroyl.2.mercaptohexane.66. acaricide, insecticide and / or fungicide composition according to claim 25, containing as active ingredient difuroyl.2.mercaptohexane. 67. Compositions acaricides, insecticides et/ou * fongicides suivant l'une ou l'autre des revendications 25 à 66 sous forme de liquide à pulvériser, de solution à - 20 - ! i _____. / .· . - ...... ..... ..... , ? frictionner ou tamponner, sous forme de shampooing ou sous forme d’onguent. - / , »567. Acaricidal, insecticidal and / or * fungicidal compositions according to either of claims 25 to 66 in the form of a liquid to be sprayed, a solution of 20! i _____. /. ·. - ...... ..... .....,? rub or dab, as a shampoo or as an ointment. - /, ”5
LU83725A 1981-10-29 1981-10-29 SULPHIDIC ORGANIC COMPOUNDS AND THEIR USE AS ACARICIDES, INSECTICIDES AND / OR FUNGICIDES LU83725A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
LU83725A LU83725A1 (en) 1981-10-29 1981-10-29 SULPHIDIC ORGANIC COMPOUNDS AND THEIR USE AS ACARICIDES, INSECTICIDES AND / OR FUNGICIDES
AT82201292T ATE17635T1 (en) 1981-10-29 1982-10-18 ACARICIDAL COMPOSITIONS.
DE8282201292T DE3268870D1 (en) 1981-10-29 1982-10-18 ACARICIDAL COMPOSITIONS
EP82201292A EP0078562B1 (en) 1981-10-29 1982-10-18 Acaricidal compositions
CA000413813A CA1173747A (en) 1981-10-29 1982-10-20 Acaricidal compositions
AU89750/82A AU8975082A (en) 1981-10-29 1982-10-25 Sulfur acaricidal compositions

Applications Claiming Priority (2)

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LU83725A LU83725A1 (en) 1981-10-29 1981-10-29 SULPHIDIC ORGANIC COMPOUNDS AND THEIR USE AS ACARICIDES, INSECTICIDES AND / OR FUNGICIDES
LU83725 1981-10-29

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LU83725A1 true LU83725A1 (en) 1983-06-07

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LU83725A LU83725A1 (en) 1981-10-29 1981-10-29 SULPHIDIC ORGANIC COMPOUNDS AND THEIR USE AS ACARICIDES, INSECTICIDES AND / OR FUNGICIDES

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Country Link
EP (1) EP0078562B1 (en)
AT (1) ATE17635T1 (en)
AU (1) AU8975082A (en)
CA (1) CA1173747A (en)
DE (1) DE3268870D1 (en)
LU (1) LU83725A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0472497A1 (en) * 1990-08-21 1992-02-26 Ciba-Geigy Ag Thiobutyric acid derivatives
JP2008538199A (en) * 2005-01-26 2008-10-16 メリアル リミテッド Substituted thioethers as pesticides.

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2259869A (en) * 1939-09-30 1941-10-21 Shell Dev Insecticide and repellent
BE603541A (en) * 1960-05-09
DE1793480A1 (en) * 1968-09-24 1972-02-24 Basf Ag fungicide
GB1501501A (en) * 1975-01-02 1978-02-15 Realisations Scient Soc Et Acaricidal and ovicidal compositions
US4095970A (en) * 1976-06-16 1978-06-20 Stauffer Chemical Company 2,6-Dichlorothiolbenzoates and use thereof as plant growth regulators
GB1594962A (en) * 1978-02-02 1981-08-05 Shell Int Research Pesticidal benzyl thio-carboxylate derivatives

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EP0078562A1 (en) 1983-05-11
CA1173747A (en) 1984-09-04
EP0078562B1 (en) 1986-01-29
DE3268870D1 (en) 1986-03-13
AU8975082A (en) 1983-05-05
ATE17635T1 (en) 1986-02-15

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