FR2465711A1 - Systemic fungicide 2-N-phenyl-acylamino-acetaldehyde derivs. - prepd. e.g. by reaction of halo-acetaldehyde cpds. with N-acyl-aniline cpds., useful against phytophthora and pythium - Google Patents
Systemic fungicide 2-N-phenyl-acylamino-acetaldehyde derivs. - prepd. e.g. by reaction of halo-acetaldehyde cpds. with N-acyl-aniline cpds., useful against phytophthora and pythium Download PDFInfo
- Publication number
- FR2465711A1 FR2465711A1 FR8015077A FR8015077A FR2465711A1 FR 2465711 A1 FR2465711 A1 FR 2465711A1 FR 8015077 A FR8015077 A FR 8015077A FR 8015077 A FR8015077 A FR 8015077A FR 2465711 A1 FR2465711 A1 FR 2465711A1
- Authority
- FR
- France
- Prior art keywords
- sep
- alkyl
- hydrogen
- alkoxy
- formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000006243 chemical reaction Methods 0.000 title description 7
- 230000000855 fungicidal effect Effects 0.000 title description 6
- 241000233614 Phytophthora Species 0.000 title description 3
- 230000009885 systemic effect Effects 0.000 title description 3
- 241000233639 Pythium Species 0.000 title description 2
- 239000000417 fungicide Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- -1 tetrahydro-2-furyl Chemical group 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 127
- 150000001875 compounds Chemical group 0.000 claims description 50
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 37
- 239000004480 active ingredient Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 206010061217 Infestation Diseases 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Chemical class 0.000 claims description 6
- 239000002184 metal Chemical class 0.000 claims description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 230000003032 phytopathogenic effect Effects 0.000 claims description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- AOHSPBYDCWWYOB-UHFFFAOYSA-N N-(1,1-dimethoxypropan-2-yl)-N-(2,6-dimethylphenyl)-2-methoxyacetamide Chemical compound COC(C(C)N(C(COC)=O)C1=C(C=CC=C1C)C)OC AOHSPBYDCWWYOB-UHFFFAOYSA-N 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- JSLKRLJOJLHMET-UHFFFAOYSA-N N-(2,2-dimethoxyethyl)-N-(2,6-dimethylphenyl)-2-methoxyacetamide Chemical compound COC(CN(C(COC)=O)C1=C(C=CC=C1C)C)OC JSLKRLJOJLHMET-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 244000005700 microbiome Species 0.000 claims 7
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 9
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003641 microbiacidal effect Effects 0.000 abstract description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 abstract 1
- 150000004696 coordination complex Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
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- 238000000034 method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
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- 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
- C07D307/10—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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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
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- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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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
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- 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
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- C07D317/28—Radicals substituted by nitrogen atoms
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
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Abstract
Description
La présente invention concerne des composés de formule I
où R1 et R2 représentent indépendamment l'un de l'autre un alcoyle en C1 à C3, un alcoxy en C1 à C3 ou un halogène;
R3 représente un hydrogène, un alcoyle en C1 à C3 ou un halogène,
R4 représente un hydrogène ou un méthyle, où la somme des atomes de carbone dans R1, R2, R3 et
R4 ne dépasse pas 6 et où R5 représente un hydrogène ou un alcoyle en C1 à C3,
R6 un ss-(C1-C4)-alcoxyéthyle ou un groupe 2-furyle, r-tétrahydrofuryle ou -CH2Z éventuellement substitué par un halogène, où Z représente l'un des groupes suivants
a) -OR7, -SR7
c) -OSO2R10 d) -OCR11
o
e) un 1,2-pyrazole, un 1,3-imidazole, un 1,2,4- triazole y compris leurs sels et complexes métalliques, et R7 représente un groupe alcoyle en C1 à C6, alcényle en C3 à C4 ou alcynyle en C3 à C4 éventuellement substitué par un alcoxy en C1 a C2; R8 représente un hydrogène ou un alcoyle en C1 à C3; ;R9 un alcoyle en
C1 à C3 ou un groupe phényle éventuellement substitué par un halogène ou un méthyle et R10 un alcoyle en C1 à C4, une mono- ou di-(C1-C3)-alcoylamine, R11 un groupe alcoyle en C1 à C3 êventuellement substitué par un al- coxy en C1 à C2 et X représente -CHO ou
où Y1 et Y2 représentent indépendamment l'un de l'autre un alcoyle en C1 à C4 ou, ensemble, forment un pont alcoylène en C à C éventuellement mono- ou 3 polysubstitué par un~alcoyle en C1 à C3, ou forment ensemble un noyau 1,2-cyclohexane.The present invention relates to compounds of formula I
wherein R1 and R2 independently of one another are C1-C3 alkyl, C1-C3 alkoxy or halogen;
R3 represents hydrogen, C1-C3 alkyl or halogen,
R4 represents hydrogen or methyl, where the sum of the carbon atoms in R1, R2, R3 and
R4 does not exceed 6 and where R5 is hydrogen or C1-C3 alkyl,
R6 is ss- (C1-C4) -alkoxyethyl or 2-furyl, r-tetrahydrofuryl or -CH2Z optionally substituted by halogen, where Z is one of the following groups
a) -OR7, -SR7
c) -OSO2R10 d) -OCR11
o
e) a 1,2-pyrazole, a 1,3-imidazole, a 1,2,4-triazole including their salts and metal complexes, and R7 represents a C1-C6 alkyl, C3-C4 alkenyl or alkynyl group; C3 to C4 optionally substituted with C1 to C2 alkoxy; R8 represents hydrogen or C1-C3 alkyl; R9 alkyl in
C1 to C3 or a phenyl group optionally substituted by halogen or methyl and R10 a C1 to C4 alkyl, a mono- or di- (C1-C3) alkylamine, R11 a C1 to C3 alkyl group optionally substituted with a C1 to C2 and X represents -CHO or
wherein Y1 and Y2 independently of one another are C1-C4 alkyl or together form a C1-C4 alkylene bridge optionally mono- or polysubstituted by C1-C3 alkyl, or together form a 1,2-cyclohexane nucleus.
Les composés de formule I se décrivent sous la forme aldehyde comme phénylaminoalcanals et sous la forme acétalisée comme phénylaminoacétals. The compounds of formula I are described in the aldehyde form as phenylaminoalkanals and in the acetalized form as phenylaminoacetals.
Sous le terme alcoyle ou fraction alcoyle d'un autre substituant il faut comprendre selon le nombre d'atomes de carbone donné les groupes suivants: méthyle, éthyle, propyle, butyle, pentyle, hexyle ainsi que leurs isomères par exemple iso-propyle, iso-butyle, sec-butyle, tert-butyle, iso-pentyle, etc. Alcoylène représente par exemple un méthylène, un éthylène, un propylène, etc. Alcényle représente par exemple un vinyle, un allyle, un 2-butényle, etc. Alcynyle représente surtout un propargyle, Halogène représente un fluor, un chlore, un brome ou un iode. Under the term alkyl or alkyl moiety of another substituent, the following groups must be understood according to the number of carbon atoms given: methyl, ethyl, propyl, butyl, pentyl, hexyl and their isomers, for example iso-propyl, iso butyl, sec-butyl, tert-butyl, iso-pentyl, etc. Alkylene is, for example, methylene, ethylene, propylene, etc. Alkenyl represents for example a vinyl, an allyl, a 2-butenyl, etc. Alkynyl is predominantly propargyl, Halogen is fluorine, chlorine, bromine or iodine.
On peut préparer les composés de formule I selon toute une série de procédés, comme par exemple mentionné ci-dessous. Dans les formules I a-b et II à
XV R1 à R11 ainsi que X, Y1 et Y2 ont les significations données pour la formule I, liai représente un halogène, de préférence le chlore ou le brome et M un hydrogène ou un cation métallique, de préférence alcalin ou alcalino-terreux.
The compounds of formula I can be prepared by a variety of processes, such as, for example, mentioned below. In formulas I ab and II to
R 1 to R 11 as well as X, Y 1 and Y 2 have the meanings given for formula I, IIa is halogen, preferably chlorine or bromine and M is hydrogen or a metal cation, preferably alkaline or alkaline earth metal.
Cn peut ici employer de préférence un dérivé réactif d'un composé de formule III, comme par exemple un haqlogénure d'acide, un anhydride d'acide ou un ester. In this case, a reactive derivative of a compound of the formula III, for example an acid anhydride, an acid anhydride or an ester, may preferably be used.
Dans de nombreux cas on a intérêt à utiliser des liants acides ou des agents de condensation. Comme agents de ce type il faut mentionner par exemple les amines tertiaires comme les trialcoylamines (par exemple la triéthylamine, la pyridine et les bases pyridilues ou les bases inorganiques, comme les oxydes, hydroxydes, ca bonates acides, carbonates ou hydrures de métaux alcalins et alcafflino-terrew: ainsi eue l'acétate de sodium. Comme liant acide on peut en outre employer le produit de départ II. In many cases it is advantageous to use acidic binders or condensation agents. Examples of agents of this type are tertiary amines such as trialkylamines (for example triethylamine, pyridine and pyridyl bases or inorganic bases, such as oxides, hydroxides, alkali metal carbonates or hydrides of alkali metals and alkaffinino-terrew: thus sodium acetate As the acidic binder, it is also possible to use starting material II.
On peut également effectuer le procédé de pré paration A sans liant acide, et dans certains cas il est indiqué de faire passer de l'azote pour éliminer l'halohydrate formé. Dans d'autres cas il est très intéressant d'ajouter du diméthylformamide comme catalyseur de la rracti.cn. The preparative process A can also be carried out without an acidic binder, and in some cases it is advisable to pass nitrogen to remove the formed hydrohalide. In other cases it is very interesting to add dimethylformamide as a catalyst for rracti.cn.
R6 possède une signification différente de
R6 has a different meaning than
On transforme ici le composé de formule IV tout d'abord avec du butyllithium o de l'hydrure de sodium pour donner le sel alcalin correspendant, ou encore on effectue le procédé en présence d'un liant acide de manière analogue au procédé A, de préférence en ajoutant des quantités catalytiques d'iedure alcalin. The compound of formula IV is converted here firstly with butyllithium or sodium hydride to give the corresponding alkaline salt, or the process is carried out in the presence of an acidic binder analogously to process A, preferably by adding catalytic amounts of alkali metal.
C. Lorsque R6 représente -CH2OSO2R10 ou
C. When R6 represents -CH2OSO2R10 or
On utilise de préférence un sel, surtout un sel alcalin de formule VI. A salt, especially an alkaline salt of formula VI, is preferably used.
D. Lorsque R6 représente -CH2XR7
-CH2NH-N(R8)(R9) ou un azolylméthyle (azole = 1,2-pyrazole, 1,3-iodazole ou 1,2,4-triazole) :
D. When R6 represents -CH2XR7
-CH2NH-N (R8) (R9) or an azolylmethyl (azole = 1,2-pyrazole, 1,3-iodazole or 1,2,4-triazole):
Lorsque M est un hydrogène, il est indiqué d'employer un agent salificateur, comme par exemple un oxyde, un hydroxyde, un hydrure, etc, de métaux alcalins ou alcalino-terreux. Lorsqu'on utilise des produits de départ de formule SII, on obtient le produit final sous forme d'halohydrate. When M is hydrogen, it is advisable to use a salifying agent, such as an oxide, a hydroxide, a hydride, etc., of alkali or alkaline earth metals. When starting materials of formula SII are used, the final product is obtained in the form of a hydrohalide.
Avec des bases faibles on obtient à partir de cela à la température ambiante ou à une température légèrement augmentée le composé hydrazino libre. I1 convient d'employer à cet effet par exemple les carbonates alcalins. With weak bases, the free hydrazino compound is obtained from this at room temperature or at a slightly increased temperature. For this purpose, for example, alkaline carbonates should be used.
E. Lorsque R6 représente un ss-(C1-C4)-alcoxy- éthyle
E. When R6 represents ss- (C1-C4) -alkoxyethyl
On travaille ici de manière analogue au procédé D. We work here analogously to the method D.
J?. Lorsque R6 représente ss-(C1-C4)-alcoxyéthyle
J ?. When R6 represents ss- (C1-C4) -alkoxyethyl
Dans ce procédé on procède avec l'alcool ou avec l'alcoolate XV )M= atome métallique) à une addition de Michael. In this process, the alcohol or the alkoxide XV) M = metal atom) is used to add Michael.
G. En particulier, lorsque X représente -CHO, on peut également procéder à la réaction suivante
G. In particular, when X represents -CHO, the following reaction can also be carried out
On préfère les acétals en chaîne ouverte de formule Ia, où X représente
et où Y1 et Y2 représentent des alcoyles en
C1 à C4. La séparation s'effectue au mieux lorsqu'on utilise des acides dilués, comme par exemple des acides minéraux. Open-chain acetals of formula Ia, where X is
and where Y1 and Y2 represent alkyls in
C1 to C4. Separation is best done when dilute acids, such as mineral acids, are used.
H. En particulier lorsque Y1 et Y2 forment un pont alcoylène en C2 à C3, qui est éventuellement monoou polysubstitué par un alcoyle en C1 à C3 ou lorsque
Y1 et Y2 représentent un noyau hexagonal hydrogéné condensé en position 1,2
H. Especially when Y1 and Y2 form a C2-C3 alkylene bridge, which is optionally mono or polysubstituted by C1-C3 alkyl or when
Y1 and Y2 represent a hydrogenated hexagonal ring condensed at the 1,2 position
On fait ici réagir un acétal en chaque ouverte de formule Ib, où Y1 et Y2 représentent de préférence un alcoyle en C1 à C4 avec un diol de formule XVII, où A représente un cyclohexylène-1,2 ou un éthylène-1,2 ou propylène-1,3 éventuellement substitué par un ou deux gropes alcoyle en C1 à C. Pans certains cas il peut etre intéressant de tavailler à des températures plus élevées; la présence d'un acide peut également se révéler favorahle dans un tel procédé. An acetal in each open of formula Ib is reacted, where Y1 and Y2 are preferably C1-C4 alkyl with a diol of formula XVII, where A is 1,2-cyclohexylene or 1,2-ethylene or 1,3-propylene optionally substituted with one or two C1-C4 alkyl groups. In some cases it may be advantageous to work at higher temperatures; the presence of an acid may also be favored in such a process.
Gans tous les procédés on peut utiliser essentiellement des solvants qui sont inertes vis-à-vis des participants à la réaction. Comme exemples de tels sol vants on peut citer
Les hydrocarbures aromatiques ou aliphatiques, comme le benzène, le toluène, les xylènes, l'éther de pétrole ; les hydrocarbures halogénés cern-me le ehloro- benzène, le chlorure de méthylène, le chlorure d'éthylène, le chloroforme, le tétrachloréthylène ; les éthers et les composés étherés comme les dialcoyléthers, par exemple le t-butylméthyléther, le dioxanne, le tétra hydrofuanne ; les nitriles comme l'acétonitrile ; les amides N,N-dialcoylés comme le diméthylformamide ; le diméthylsulfoxyde; les cétones comme la méthyléthyl- cétone et les mélanges de tels solvants entre eux.In all processes, essentially solvents which are inert to the reaction participants can be used. Examples of such solids include
Aromatic or aliphatic hydrocarbons, such as benzene, toluene, xylenes, petroleum ether; halogenated hydrocarbons such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, tetrachlorethylene; ethers and ether compounds such as dialkylethers, for example t-butyl methyl ether, dioxane, tetrahydrofuane; nitriles such as acetonitrile; N, N-dialkylamides, such as dimethylformamide; dimethylsulfoxide; ketones such as methyl ethyl ketone and mixtures of such solvents with each other.
Tous les produits de départ se préparen tar des procédés classiques. All starting materials are prepared by conventional methods.
Cf. J. Org. Chem. 30, 4101 (1965),
Tetrahedron 1967, 487
Tetrahedron 1967, 493
Les différents procédés font également de l'invention. Les produits de départ sont égal en partie nouveaux et relèvent de l'invention ; ils ont une action fongicide.See J. Org. Chem. 30, 4101 (1965),
Tetrahedron 1967, 487
Tetrahedron 1967, 493
The different methods also make the invention. The starting materials are partly new and come under the invention; they have a fungicidal action.
Dans les références suivantes on cription d'anilides acylés comme herbicides ; il n'@ pas d'indication d'action fonmicide, étant den@e @@ cun des composés mentionnés dans ces dosumonne na @ sente une action fongicide utilisable :
Brevet américain 3 t
Brevet américain 4 115 464
Brevet américain 3 946 043
Brevet américain 3 946 044
Brevet américain 3 946 045
Les composés de formule I poceèdent en perétion voisine de X un atoms de carbone asymitrique dans la chaîne latérale et peuvent étre dédoublés de mauière habituelle pour donner les antipodes optiques (séparation du racémate); ainsi par exemple par cristallisa- tion fractionnée dans sels de II avec un acide optiquement actif (comme par exemple l'acide D-lactique) et réaction ultérieure des composés optiquement pare de II et I.In the following references, acylated anilides are listed as herbicides; there is no indication of a fungicidal action, being one of the compounds mentioned in these Dosumonne has a fungicidal action usable:
US patent 3 t
US Patent 4,115,464
US Patent 3,946,043
US Patent 3,946,044
US Patent 3,946,045
The compounds of Formula I have an asymmetric carbon atom in the side chain close to X and can be split in the usual way to give the optical antipodes (racemate separation); thus for example by fractional crystallization in II salts with an optically active acid (such as, for example, D-lactic acid) and subsequent reaction of the optically active compounds of II and I.
Selon les substitutions on peut avair d'autre atomes de carbone asymétriques dans la meléeule. Depending on the substitutions, there may be other asymmetric carbon atoms in the melee.
Indépendamment de l'isomérie optique mention née, on observe en règle générale une isomérie atropique autour de l1axe Phényl
dans les cas où le noyau phényle est substitué au moins en position 2,6 et simultanément de façon asymétrique par rapport à cet axe (éventuellement donc également lorsque des substituants supplémentaires sont présents.Independently of the optical isomerism mentioned, atrophic isomerism is generally observed around the Phenyl axis.
in cases where the phenyl ring is substituted at least at the 2,6-position and simultaneously asymmetrically with respect to this axis (thus possibly also when additional substituents are present.
Dans la mesure où l'on ne procède pas à une synthèse orientée vers l'isolement des isomères purs, un produit de formule I se présente normalement sous forme de mélange de ces isomères possibles. Insofar as an isolation oriented synthesis of the pure isomers is not carried out, a product of the formula I is normally in the form of a mixture of these possible isomers.
Les composés de formule I peuvent être utilisés seuls ou avec des supports et/ou autres additifs appropriés. Les supports et additifs appropriés peuvent être solides ou liquides et correspondent aux produits habituels dans la technique de formulation, comme par exemple les produits minéraux naturels ou régénérés, les solvants, les dispersants, les agents mouillants, les colles, les épaississants, les liants et les engrais. The compounds of formula I may be used alone or with suitable carriers and / or other additives. Suitable supports and additives may be solid or liquid and correspond to the usual products in the formulation art, such as natural or regenerated mineral products, solvents, dispersants, wetting agents, glues, thickeners, binders and the like. fertilizers.
La teneur en matière active dans les agents du commerce s'établit entre 0,1 et 90 ; la fraction représentée par les additifs se situe entre 10 et 99,9 %, et parmi les additifs il faut compter de O à 30 f d'un agent tensio-actif. The content of active ingredient in the commercial agents is between 0.1 and 90; the fraction represented by the additives is between 10 and 99.9%, and among the additives it is necessary to count from 0 to 30% of a surfactant.
Aux fins d'application, les composés de formule I peuvent se présenter sous les formes de base suivantes (où les pourcentages pondéraux entre parenthèses représentent les quantités avantageuses de matière active). For the purpose of application, the compounds of formula I may be in the following basic forms (where the weight percentages in parentheses represent the advantageous amounts of active ingredient).
Formes de base solides : Produits pour poudrage et pro
duits d'épandage (jusqu'à 10 ), granulés,
granulés enrobés , granulés imprégnés et granu
lés homogènes, pastilles (grains) (1 à 90 /a'). Solid basic shapes: Dusting and pro products
spreading products (up to 10), granules,
coated granules, impregnated granules and granules
homogeneous, pellets (grains) (1 to 90 / a ').
Formes de base liquides a) Concentres de matière active dispersables dans l'eau:
Poudres mouillables (wettable powders) et pâtes
(25-90 ,'- dans l'emballage du commerce, 0,01 à 15 70
en solution prête à l'emploi); concentrés d'émul
sions et de solutions (10 à 50 %; 0,01 à 15 % en
solution prête à l'emploi); b) Solutions (0,1 à 20 ,'J); aérosols.Liquid basic forms (a) Water-dispersible active ingredient concentrates:
Wettable powders and pasta
(25-90, - in the commercial package, 0.01 to 15 70
in ready-to-use solution); concentrated emulators
and solutions (10 to 50%, 0.01 to 15% in
ready-to-use solution); b) Solutions (0.1 to 20, J); aerosols.
Ces agents relèvent également de l'invention. These agents also come under the invention.
On a trouvé de façon surprenante que les composés dont la structure répond à la formule I ont un très bon champ d'activité microbicide pour les besoins pratiques de protection des plantes cultivées. Au sens de l'invention les plantes cultivées sont par exemple les céréales, le mais, le riz, le-s légumes, la betterave sucrière, le soja, les arachides, les arbres fruitiers, les plantes d'ornement, mais surtout la vigne, le houblon, les cucurbitacées (concombres, citrouilles, melons), les solanacées comme les pommes de térre, le tabac et les tomates, ainsi que les cultures de bananes, de cacao et de caoutchouc naturel. It has surprisingly been found that compounds whose structure corresponds to formula I have a very good field of microbicidal activity for the practical needs of crop protection. For the purposes of the invention, the cultivated plants are, for example, cereals, maize, rice, vegetables, sugar beet, soya, peanuts, fruit trees, ornamental plants, but especially grapes. , hops, cucurbits (cucumbers, pumpkins, melons), nightshades such as potatoes, tobacco and tomatoes, as well as banana, cocoa and natural rubber crops.
Avec les matières actives de formule I on peut contenir ou anéantir les champignons qui apparaissent sur les plants ou parties de plants (fruits, fleurs, feuilles, tiges, tubercules, racines) de ces cultures utiles et d'autres cultures utiles apparentées, les parties de plantes croissant ultérieurement restant épargnées par les champignons de cette espèce. Les matières actives sont efficaces contre les champignons phytopathogènes appartenant aux classes suivantes
Ascomycètes (par exemple Venturia); mais surtout contre les Oomycètes appartenant à la classe des Phytomycètes comme les Péronosporales (Phytophthora, Pythium,
Plasmopara). Les composés de formule I sont également actifs contre les parasites du type Cercospora.With the active ingredients of formula I it is possible to contain or annihilate the fungi which appear on the plants or parts of plants (fruits, flowers, leaves, stems, tubers, roots) of these useful cultures and other related useful cultures, the parts of later growing plants remaining untouched by fungi of this species. The active ingredients are effective against phytopathogenic fungi belonging to the following classes
Ascomycetes (eg Venturia); but especially against the Oomycetes belonging to the class of Phytomycetes like Peronosporales (Phytophthora, Pythium,
Plasmopara). The compounds of formula I are also active against Cercospora parasites.
En outre les composés de formule I ont une action systémique. On peut également les employer comme désinfectants pour traiter les semences (fruits, tubercules, graines) et les jeunes pousses afin de les protéger contre les infections provoquées par les champignons ainsi que contre les champignons phytopatho- gènes que l'on trouve dans le sol. In addition, the compounds of formula I have a systemic action. They can also be used as disinfectants to treat seeds (fruits, tubers, seeds) and young shoots to protect them against infections caused by fungi and phytopathogenic fungi found in the soil.
L'invention concerne également en outre l'ap- plication des composés de formule I à la lutte contre les mioroerganismes phytopathogènes. The invention also relates to the application of the compounds of formula I to the control of phytopathogenic mioroerganisms.
On préfère les types de substituants suivants ou leurs combinaisons :
Pour R1 : - a) C1-C2-alcoyle, C1-C2-alcoxy
b) CH3, OCH3
Pour R2 : - a) CH3, OCH3, Halogène
b) CH3, chlore
Pour R3 : - a) Hydrogène, CH3, Halogène
b) Hydrogène
Pour R4 : - a) Hydrogène, CH3
b ) Hydrogène
Pour R5 : - CH3
Pour X :
The following types of substituents or their combinations are preferred:
For R1: - a) C1-C2-alkyl, C1-C2-alkoxy
b) CH3, OCH3
For R2: - a) CH3, OCH3, Halogen
b) CH3, chlorine
For R3: - a) Hydrogen, CH3, Halogen
b) Hydrogen
For R4: - a) Hydrogen, CH3
b) Hydrogen
For R5: - CH3
For X:
Ta et Y2 représentent un alcoyle en C1 à C4 ou éventuellement forment ensemble un pont alcoylène en C2 à C3 mono- ou polysubstitué par un alcoyle en
C1 à C3 ou forment ensemble un noyau 1,2-cyclohexane.Ta and Y2 represent a C1 to C4 alkyl or optionally together form a C2 to C3 alkylene bridge mono- or polysubstituted by alkyl
C1 to C3 or together form a 1,2-cyclohexane ring.
Pour R6 : - a) 2-furyle, 2-tétrahydrofuryle, ss-(C1-C2
alcoxy)-éthyle, CH2Z
b) 2-furyle, 2-tétrahydrofuryle,
CH2CH2OCH3, CH2Z où Z représente
a) -O-R7 (R7=C1-C3 -alcoyle)
(R8 et R9 = C1-C2-alcoyle)
c) -OSO2R10 (R10=C1-C2-a'coyle, méthyl
amine)
d) 1,2,4-triazole
Pour R7 : un alcoyle en C1 à C4 éVentuellement substi
tué par un alcoxy en C1 à C2, un alcényle en
C3 à C4, un alcyhyle en C3 à C4 pour R8 : un alcoyle en C1 à C3 pour R9 : un alcoyle en C1 à C3 pour R10: un alcoyle en Ci à C2, la méthylamine.For R6: - a) 2-furyl, 2-tetrahydrofuryl, ss- (C1-C2
alkoxy) -ethyl, CH2Z
b) 2-furyl, 2-tetrahydrofuryl,
CH2CH2OCH3, CH2Z where Z represents
a) -O-R7 (R7 = C1-C3-alkyl)
(R8 and R9 = C1-C2-alkyl)
c) -OSO2R10 (R10 = C1-C2-alkyl, methyl)
amine)
d) 1,2,4-triazole
For R7: a C1-C4 alkyl which is
killed by C1-C2 alkoxy, alkenyl
C3 to C4, C3 to C4 alkyhyl for R8: C1 to C3 alkyl for R9: C1 to C3 alkyl for R10: C1 to C2 alkyl, methylamine.
On a également par exemple les groupes préfé rs suivants
R1 = C1-C2-alcoyle, C1-C2-alcoxy
R2 = CH3, -OCH3, Halogène
R3 = Hydrogène, CH3, Halogène
R4 = Hydrogène, CH3
R5 = Méthyle
We also have, for example, the following preferred groups
R1 = C1-C2-alkyl, C1-C2-alkoxy
R2 = CH3, -OCH3, Halogen
R3 = Hydrogen, CH3, Halogen
R4 = Hydrogen, CH3
R5 = Methyl
Dans ces formules Y1 et R2 représentent un alcoyle en C1 à c4 ou ensemble un pont alcoylène en C2 à
C3 mono- ou polysubstitut par un alcoyle en C1 à C3 on non-substitué, ou forment ensemble un noyau 1,2-cyclohexanone.In these formulas Y1 and R2 represent a C1-C4 alkyl or together a C2-C2 alkylene bridge.
C3 mono- or polysubstituted with a C1-C3 alkyl are unsubstituted, or together form a 1,2-cyclohexanone ring.
R6 = 2-furyle, 2-tétrahydrofuryle, ss-(C1-C2-alcoxy)
éthyle, -CH2Z, où Z représente :
a -OR7, -SR7
R6 = 2-furyl, 2-tetrahydrofuryl, ss- (C1-C2-alkoxy)
ethyl, -CH2Z, where Z is:
a -OR7, -SR7
c) -OSO2R10
d) 1,2-pyrazole, 1,3-imidazole, 1,2,4-triazole y compris leurs sels et complexes métalliques. c) -OSO2R10
d) 1,2-pyrazole, 1,3-imidazole, 1,2,4-triazole including their salts and metal complexes.
R7 = alcoyle en C1 à C4 éventuellement substitué par un
alcoxy en C à C2, alcényle en C3 à C4, alcynyle
en C3 à C4,
R8 = C1-C3-alcoyle
R9 = C1-C3-alcoyle
R10= C1-C2-alcoyle, méthylamine.R7 = C1 to C4 alkyl optionally substituted with a
C 1 -C 2 alkoxy, C 3 -C 4 alkenyl, alkynyl
in C3 to C4,
R8 = C1-C3-alkyl
R9 = C1-C3-alkyl
R10 = C1-C2-alkyl, methylamine.
Autre groupe préféré :
R1 = CH3, OCH
R2 = CH3, chlore
R3 = Hydrogène
R4 = Hydrogène
R5 = CH3
Another favorite group:
R1 = CH3, OCH
R2 = CH3, chlorine
R3 = Hydrogen
R4 = Hydrogen
R5 = CH3
Dans ces formules Y1 et Y2 représentent un alcoyle en C1 à C4 ou forment ensemble un pont alcoylène mono- ou polysubstitué par un alcoyle en C1 à C3 ou non-substitué. In these formulas Y1 and Y2 represent C1-C4 alkyl or together form an alkylene bridge mono- or polysubstituted with C1-C3 alkyl or unsubstituted.
R6 = 2-furyle, 2-tétrahydrofuryle, -CH2CH2OCH3, -CH2Z
où Z représente
a) -OR7 (R7 = C1-C3-alcoyle)
(R8 = C1-C2-alcoyle) (R9 = C1-C2-alcoyle)
c) -OSO2R10 (R10 - C1-C2-alcoyle, méthylamine)
d) 1,2,4-triazole.R6 = 2-furyl, 2-tetrahydrofuryl, -CH2CH2OCH3, -CH2Z
where Z represents
a) -OR7 (R7 = C1-C3-alkyl)
(R8 = C1-C2-alkyl) (R9 = C1-C2-alkyl)
c) -OSO2R10 (R10-C1-C2-alkyl, methylamine)
d) 1,2,4-triazole.
Les exemples suivants servent à préciser l'invention sans la limiter. Les températures sont données en degrés Celalus. The following examples serve to clarify the invention without limiting it. Temperatures are given in Celalus degrees.
Sauf indication contraire, lorsque l'on nomme une matière active de formule I il s'agit toujours du mélange racémique. Unless otherwise indicated, when an active ingredient of formula I is designated it is always the racemic mixture.
Exemple 1 a) Préparation du produit intermédiaire
N-(2,6-diméthylphényl)-amino-acéta1déhyde-diméthyl- acétal
Dans 8,8 g d'hydrure de sodium à 55 % dans 50 ml de toluène on verse goutte à goutte tout en agitant et en faisant passer de l'azote à une température de bain de 1400 24,2 g de 2,6-diméthylaniline dans 20 ml de toluène, on chauffe au reflux pendant 3 heures jusqu'à la fin du dégagement d'hydrogène puis on ajoute 37,2 g de bromacétaldéhyde-dimêthylacétal. Après avoir chauffé encore pendant 24 heures au reflux on refroidit, on dilue avec 500 ml d'eau, on sépare la phase toluène, on la lave avec un peu d'eau, on sèche sur sulfate de sodium, on filtre et on fait évaporer le -solvant. On fait subir au résidu huileux une distillation fractionnée sous un vide poussé; Peb 1000/0,09 mbar.Example 1 a) Preparation of the intermediate product
N- (2,6-dimethylphenyl) -amino-acetaldehyde dimethylacetal
8.8 g of 55% sodium hydride in 50 ml of toluene are added dropwise with stirring and passing through nitrogen at a bath temperature of 1400. dimethylaniline in 20 ml of toluene, heated at reflux for 3 hours until the end of the evolution of hydrogen and then 37.2 g of bromo-acetaldehyde-dimethylacetal are added. After refluxing for a further 24 hours, the mixture is cooled, diluted with 500 ml of water, the toluene phase is separated off, washed with a little water, dried over sodium sulphate, filtered and evaporated. the solvent. The oily residue is subjected to fractional distillation under high vacuum; Peb 1000 / 0.09 mbar.
b) Préparation du produit final
(Composé n 3)
N-(2,6-diméthylphényl)-N-méthoxyacétyl-amino-acétal déhyde-diméthylacétal
Pans 15,4 g de N-(2,6-diméthylphényl)-amino- acétaldéhyde-diméthylacétal et 6,3 g de pyridine dans 100 nil de toluène on verse goutte à goutte à 100 8,7 b de chlorure de l'acide méthoxyacéticue. Lorsque la réaction faiblement exothermique s'est arrêtée, on agite pendant 3 heures à la température ambiante, on sépare du chlorhydrate de pyridine par filtration, on lave 2 fois la solution réactionnelle avec à chaque fois 50 ml d'eau, on sèche sur sulfate de sodium, on filtre et on fait évaporer le solvant.On fait subir au résidu huileux une distillation fractionnée sous un vide poussé ; Peb 129-130 /0,05 mbar.b) Preparation of the final product
(Compound No. 3)
N- (2,6-dimethylphenyl) -N-methoxyacetyl-amino-acetaldehyde-dimethylacetal
15.4 g of N- (2,6-dimethylphenyl) -aminoacetaldehyde dimethyl acetal and 6.3 g of pyridine in 100 ml of toluene are added dropwise to 100 8.7 g of acid chloride. méthoxyacéticue. When the weakly exothermic reaction has stopped, stirring is carried out for 3 hours at room temperature, pyridine hydrochloride is filtered off, the reaction solution is washed twice with 50 ml of water each time, and is dried over sulphate. of sodium, filtered and the solvent evaporated. The oily residue is subjected to fractional distillation under high vacuum; Peb 129-130 / 0.05 mbar.
Exemple 2 a) Préparation du produit intermédiaire
2-[N-(2,6-diméthylphényl)-amino]-propionaldéhydediméthylacétal
On traite 60,5 g de 2,6-diméthylaniline, 71,5 g de méthylglyoxal-diméthylacétal et 1,3 g d'acide sulfurique concentré en présence de 1 ,3 g de platine à 5 % sur charbon actif à 40-50 et sous une pression de 5 bar avec de l'hydrogène. Gn dilue le mélange d'hydrogénation avec 300 ml d'ester éthylique de l'acide acétique, on sépare du catalyseur par filtration, on le lave avec 100 ml d'une solution à 10 % de bicarbonate de sodium et avec de l'eau. Après séchage sur sulfate de sodium on fait évaporer le solvant et on fait subir au résidu huileux une distillation fractionnée sous un vide poussé ;Peb 77-781 /0,05 mbar. Example 2 a) Preparation of the intermediate product
2- [N- (2,6-dimethylphenyl) -amino] -propionaldéhydediméthylacétal
60.5 g of 2,6-dimethylaniline, 71.5 g of methylglyoxal dimethylacetal and 1.3 g of concentrated sulfuric acid are treated in the presence of 1.3 g of 5% platinum on 40-50 active carbon. and under a pressure of 5 bar with hydrogen. The hydrogenation mixture is diluted with 300 ml of ethyl acetate and filtered from the catalyst, washed with 100 ml of 10% sodium bicarbonate solution and with water. . After drying over sodium sulfate, the solvent is evaporated off and the oily residue is subjected to fractional distillation under high vacuum: PEb 77-781 / 0.05 mbar.
b) rréparation du produit final
(Composé n 2) 2-[N-(2,6-diméthylphényl)-N-méthoxyacétyl-amin@ propionaldéhyde-diméthylacétal.b) reparation of the final product
(Compound No. 2) 2- [N- (2,6-dimethylphenyl) -N-methoxyacetyl-aminopropionaldehyde dimethyl acetal.
Dans 14,1 g de 2-[N-(2,6-diméthylphényl) -aminoj -propionaldéhyde-diméthylacétal et 7,5 g de soude dans 150 ml de benzène, on verse gautte à gout@e tout en agitant 6,4 ml de chlorure de l'acide méthoxyacétique. 14.1 g of 2- [N- (2,6-dimethylphenyl) -amino] -propionaldehyde dimethyl acetal and 7.5 g of sodium hydroxide in 150 ml of benzene are added dropwise with stirring. ml of methoxyacetic acid chloride.
Le mélange réactionnol se réchauffe alors à 33 C. On agite pendant 1 heure o la température ambiante on filtre et on concentre le filtrat sous vide jusqu'à siccité. On cristallise le résidu huileux à partir de l'essence. On obtient 10 g de produit final de Pf 44450C.The reaction mixture then warms to 33 ° C. The mixture is stirred for 1 hour at room temperature and the filtrate is concentrated under vacuum to dryness. The oily residue is crystallized from gasoline. 10 g of final product of Pf 44450C are obtained.
EXEMPLE 3 Préparation du produit final
(Composé n 12) 2-[N-(2,6-diméthylphényl)-N-méthoxyacétyl-amino]propionaldéhyde.EXAMPLE 3 Preparation of the final product
(Compound No. 12) 2- [N- (2,6-dimethylphenyl) -N-methoxyacetylamino] propionaldehyde.
On introduit 20 g de 2-[N-(2,6-diméthylphényl)
N-méthoxyacétyl-amino]-propionaldéhyde-diméthylacétal tout en agitant à la température ambiante dans 100 d'acide chlorhydrique 2 N. A partir de la solution tout d'abord claire il se sépare au bout d'un certain temps un précipité blanc, que l'on sépare par filtration au bout d'1 heure, que l'on lave à neutralité avec de l'eau glacée et que l'on sèche. Après recristallisation à partir de l'ester éthylique de l'acide acétique, les cristaux blancs fondent à 73-75 .20 g of 2- [N- (2,6-dimethylphenyl) are introduced
N-methoxyacetylamino] -propionaldehyde dimethyl acetal while stirring at room temperature in 100 N hydrochloric acid. From the first clear solution, a white precipitate is separated after a period of time. which is filtered off after 1 hour, washed neutral with ice water and dried. After recrystallization from the ethyl ester of acetic acid, the white crystals melt at 73-75.
Exemple 4
Préparation de
(Composé n 87) 2-[N-(2,6-diméthylphényl)-N-méthoxyacétyl-amino]-propio naldéhyde-propylènacétal
On chauffe dans 150 ml de toluène sec 30,0 g de 2-[N-(2,6-diméthylphényl)-N-méthoxyacétyl-amino]propionaldéhyde-diméthylacétal, 7,7 g de propanediol1,3 et 0,1 g d'acide p-toluènesulfonique. Dans une colonne de Vigreux de 10 cm de long on distille entre 61 et 1100 un mélange de méthanol et de toluène. On continue la distillation jusqu'à ce que la température atteigne 1100 et qu'on ne distille plus que du toluène.Example 4
Preparation of
(Compound No. 87) 2- [N- (2,6-dimethylphenyl) -N-methoxyacetylamino] propionaldehydepropyleneacetal
30.0 g of 2- [N- (2,6-dimethylphenyl) -N-methoxyacetylamino] propionaldehyde dimethyl acetal, 7.7 g of propanediol, 1, 3 and 0.1 g of toluene are heated in 150 ml of dry toluene. p-toluenesulfonic acid. In a column of Vigreux 10 cm long is distilled between 61 and 1100 a mixture of methanol and toluene. The distillation is continued until the temperature reaches 1100 and only distilled toluene.
On refroidit alors la solution réaetionnelle à la température ambiante et on la lave 2 fois avec à chaque fois 100 ml de solution diluée de carbonate de sodium et une fois avec 100 ml de solution diluée de chlorure de sodium. On sèche la phase organique et on sépare le solvant par distillation. Après digestion avec de l'éther de pétrole, les cristaux blancs du composé de formule I fondent à 96,5-97,5 . The reaction solution is then cooled to room temperature and washed twice with 100 ml of dilute sodium carbonate solution each time and once with 100 ml of dilute sodium chloride solution. The organic phase is dried and the solvent is distilled off. After digestion with petroleum ether, the white crystals of the compound of formula I mp 96.5-97.5.
De manière analogue ou selon l'un des procédés ici décrits, on peut préparer les composés de formule I suivantes :
TABLEAU I (R1 = CH3, R2 = CH3, R4 = H)
In a similar manner or according to one of the processes described here, the following compounds of formula I can be prepared:
TABLE I (R1 = CH3, R2 = CH3, R4 = H)
Composé
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> 1 <SEP> H <SEP> H <SEP> -CH(OC2H3)2 <SEP> -CH2OCH3 <SEP> Peb <SEP> 146 /0,04 <SEP> mbar
<tb> 2 <SEP> H <SEP> CH3 <SEP> -CH(OCH3)2 <SEP> -CH2OCH3 <SEP> Pf <SEP> 44-45
<tb> 3 <SEP> H <SEP> H <SEP> -CH(OCH3)2 <SEP> -CH2OCH3 <SEP> Peb <SEP> 129 /0,05 <SEP> mbar
<tb> 4 <SEP> H <SEP> H <SEP> -CH(OCH3)2 <SEP> # <SEP> Pf <SEP> 90-92
<tb> 5 <SEP> H <SEP> H <SEP> -CH(OC2H5)2 <SEP> -CH2OC2H5 <SEP> Peb <SEP> 122-124
<tb> <SEP> 0,05 <SEP> mbar
<tb> 6 <SEP> H <SEP> CH3 <SEP> # <SEP> # <SEP> Huile
<tb> TABLEAU I (R1 = CH3, R2 = CH3, R4 = H)
Compound
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> 1 <SEP> H <SEP> H <SEP> -CH (OC2H3) 2 <SEP> -CH2OCH3 <SEP> Peb <SEP> 146 / 0.04 <SEP> mbar
<tb> 2 <SEP> H <SEP> CH3 <SEP> -CH (OCH3) 2 <SEP> -CH2OCH3 <SEP> Pf <SEP> 44-45
<tb> 3 <SEP> H <SEP> H <SEP> -CH (OCH3) 2 <SEP> -CH2OCH3 <SEP> Peb <SEP> 129 / 0.05 <SEP> mbar
<tb> 4 <SEP> H <SEP> H <SEP> -CH (OCH3) 2 <SEP>#<SEP> Pf <SEP> 90-92
<tb> 5 <SEP> H <SEP> H <SEP> -CH (OC2H5) 2 <SEP> -CH2OC2H5 <SEP> Peb <SEP> 122-124
<tb><SEP> 0.05 <SEP> mbar
<tb> 6 <SEP> H <SEP> CH3 <SEP>#<SEP>#<SEP> Oil
<tb> TABLE I (R1 = CH3, R2 = CH3, R4 = H)
Composé
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> 7 <SEP> H <SEP> CH3 <SEP> -CH(OCH3)2 <SEP> # <SEP> Pf <SEP> 74-76
<tb> 8 <SEP> H <SEP> CH3 <SEP> # <SEP> # <SEP> Huile
<tb> 9 <SEP> H <SEP> -C3H7-i <SEP> # <SEP> -CH2OCH3 <SEP> Huile
<tb> 10 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2OCH3 <SEP> Pf <SEP> 69-71
<tb> 11 <SEP> H <SEP> H <SEP> -CH(OCH3)2 <SEP> # <SEP> Huile
<tb> 12 <SEP> H <SEP> -CH3 <SEP> -CHO <SEP> -CH2OCH3 <SEP> Pf <SEP> 73-75
<tb> TABLEAU I (R1 = CH3, R2 = CH3, R4 = H)
Compound
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> 7 <SEP> H <SEP> CH3 <SEP> -CH (OCH3) 2 <SEP>#<SEP> Pf <SEP> 74-76
<tb> 8 <SEP> H <SEP> CH3 <SEP>#<SEP>#<SEP> Oil
<tb> 9 <SEP> H <SEP> -C3H7-i <SEP>#<SEP> -CH2OCH3 <SEP> Oil
<tb> 10 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2OCH3 <SEP> Pf <SEP> 69-71
<tb> 11 <SEP> H <SEP> H <SEP> -CH (OCH3) 2 <SEP>#<SEP> Oil
<tb> 12 <SEP> H <SEP> -CH3 <SEP> -CHO <SEP> -CH2OCH3 <SEP> Pf <SEP> 73-75
<tb> TABLE I (R1 = CH3, R2 = CH3, R4 = H)
Composé
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> 13 <SEP> H <SEP> -CH3 <SEP> # <SEP> # <SEP> Visqueux
<tb> 14 <SEP> H <SEP> H <SEP> -CH(OCH3)2 <SEP> -CH2OC2H5 <SEP> Peb <SEP> 130 /0,05 <SEP> mbar
<tb> 15 <SEP> H <SEP> -C2H5 <SEP> # <SEP> -CH2OCH3 <SEP> Visqueux
<tb> 16 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2OCH3 <SEP> Pf <SEP> 55-68
<tb> 17 <SEP> H <SEP> H <SEP> -CH(OC2H5)2 <SEP> # <SEP> Huile
<tb> 18 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2OSO2NHCH3 <SEP> Huile
<tb> 19 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2OC2H5 <SEP> Pf <SEP> 63-75 C
<tb> TABLEAU I (R1 = CH3, R2 = CH3, R4 = H)
Compound
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> 13 <SEP> H <SEP> -CH3 <SEP>#<SEP>#<SEP> Viscous
<tb> 14 <SEP> H <SEP> H <SEP> -CH (OCH3) 2 <SEP> -CH2OC2H5 <SEP> Peb <SEP> 130 / 0.05 <SEP> mbar
<tb> 15 <SEP> H <SEP> -C2H5 <SEP>#<SEP> -CH2OCH3 <SEP> Viscous
<tb> 16 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2OCH3 <SEP> Pf <SEP> 55-68
<tb> 17 <SEP> H <SEP> H <SEP> -CH (OC2H5) 2 <SEP>#<SEP> Oil
<tb> 18 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2OSO2NHCH3 <SEP> Oil
<tb> 19 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2OC2H5 <SEP> Pf <SEP> 63-75 C
<tb> TABLE I (R1 = CH3, R2 = CH3, R4 = H)
Composé
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> 20 <SEP> H <SEP> -CH3 <SEP> -CHO <SEP> # <SEP> Huile
<tb> 21 <SEP> H <SEP> -C3H7-1 <SEP> -CH(OCH3)2 <SEP> -CH2OCH3 <SEP> Visqueux
<tb> 22 <SEP> H <SEP> -CH3 <SEP> -CHO <SEP> #
<tb> 23 <SEP> H <SEP> -C2H5 <SEP> # <SEP> -CH2OCH3
<tb> 24 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2NH-N(CH3)2
<tb> 25 <SEP> H <SEP> -CH3 <SEP> -CHO <SEP> -CH2OC2H5
<tb> 26 <SEP> H <SEP> -CH3 <SEP> # <SEP> #
<tb> TABLEAU I (R1 = CH3, R2 = CH3, R4 = H)
Compound
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> 20 <SEP> H <SEP> -CH3 <SEP> -CHO <SEP>#<SEP> Oil
<tb> 21 <SEP> H <SEP> -C3H7-1 <SEP> -CH (OCH3) 2 <SEP> -CH2OCH3 <SEP> Viscous
<tb> 22 <SEP> H <SEP> -CH3 <SEP> -CHO <SEP>#
<tb> 23 <SEP> H <SEP> -C2H5 <SEP>#<SEP> -CH2OCH3
<tb> 24 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2NH-N (CH3) 2
<tb> 25 <SEP> H <SEP> -CH3 <SEP> -CHO <SEP> -CH2OC2H5
<tb> 26 <SEP> H <SEP> -CH3 <SEP>#<SEP>#
<tb> TABLE I (R1 = CH3, R2 = CH3, R4 = H)
Composé
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> 27 <SEP> H <SEP> -CH3 <SEP> # <SEP> #
<tb> 28 <SEP> H <SEP> -C2H5 <SEP> # <SEP> -CH2OCH3
<tb> 29 <SEP> H <SEP> -CH3 <SEP> -CH(OCH3)2 <SEP> #
<tb> 30 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2OC2H5
<tb> 31 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2OCH3
<tb> 32 <SEP> H <SEP> -CH3 <SEP> -CH(OCH3)2 <SEP> # <SEP> Huile
<tb> 33 <SEP> H <SEP> -CH3 <SEP> -CH(OCH3)2 <SEP> -CH2CH2OCH3
<tb> TABLEAU I (R1 = CH3, R2 = CH3, R4 = H)
Compound
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> 27 <SEP> H <SEP> -CH3 <SEP>#<SEP>#
<tb> 28 <SEP> H <SEP> -C2H5 <SEP>#<SEP> -CH2OCH3
<tb> 29 <SEP> H <SEP> -CH3 <SEP> -CH (OCH3) 2 <SEP>#
<tb> 30 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2OC2H5
<tb> 31 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2OCH3
<tb> 32 <SEP> H <SEP> -CH3 <SEP> -CH (OCH3) 2 <SEP>#<SEP> Oil
<tb> 33 <SEP> H <SEP> -CH3 <SEP> -CH (OCH3) 2 <SEP> -CH2CH2OCH3
<tb> TABLE I (R1 = CH3, R2 = CH3, R4 = H)
Composé
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> 34 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2OC2H5 <SEP> Huile
<tb> 35 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2OSO2NHCH3
<tb> 36 <SEP> H <SEP> -CH3 <SEP> -CH(OCH3)2 <SEP> # <SEP> Visqueux
<tb> 37 <SEP> H <SEP> -C2H5 <SEP> -CH(OC2H5)2 <SEP> -CH2OCH3
<tb> 38 <SEP> H <SEP> -CH3 <SEP> # <SEP> # <SEP> Visqueux
<tb> 39 <SEP> 3-CH3 <SEP> -CH3 <SEP> CH)OCH3)2 <SEP> # <SEP> # <SEP> 1,5469
<tb> 40 <SEP> H <SEP> -CH3 <SEP> -CH(OCH3)2 <SEP> -CH2OC2H5
<tb> TABLEAU I (R1 = CH3, R2 = CH3, R4 = H)
Compound
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> 34 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2OC2H5 <SEP> Oil
<tb> 35 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2OSO2NHCH3
<tb> 36 <SEP> H <SEP> -CH3 <SEP> -CH (OCH3) 2 <SEP>#SEP> Viscous
<tb> 37 <SEP> H <SEP> -C2H5 <SEP> -CH (OC2H5) 2 <SEP> -CH2OCH3
<tb> 38 <SEP> H <SEP> -CH3 <SEP>#<SEP>#SEP> Viscous
<tb> 39 <SEP> 3-CH3 <SEP> -CH3 <SEP> CH) OCH3) 2 <SEP>#<SEP>#<SEP> 1.5469
<tb> 40 <SEP> H <SEP> -CH3 <SEP> -CH (OCH3) 2 <SEP> -CH2OC2H5
<tb> TABLE I (R1 = CH3, R2 = CH3, R4 = H)
Composé
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> 41 <SEP> H <SEP> -CH3 <SEP> # <SEP> -CH2OCH3 <SEP> # <SEP> - <SEP> 1,5100
<tb> 42 <SEP> 3-CH3 <SEP> -CH3 <SEP> -CHO <SEP> -CH2OCH3 <SEP> # <SEP> = <SEP> 1,5346
<tb> 43 <SEP> H <SEP> -CH3 <SEP> -CH(OCH3)2 <SEP> -CH2OC3H7-i <SEP> Huile
<tb> 44 <SEP> H <SEP> -C2H5 <SEP> -CH(OCH3)2 <SEP> -CH2OCH3 <SEP> Visqueux
<tb> 45 <SEP> 3-CH3 <SEP> -CH3 <SEP> -CHO <SEP> -CH2OSO2NHCH3 <SEP> Visqueux
<tb> 46 <SEP> H <SEP> -CH3 <SEP> -CH(OCH3)2 <SEP> -CH2OCH2CH=CH2 <SEP> Huile
<tb> 47 <SEP> H <SEP> -C2H5 <SEP> -CH(OCH3)2 <SEP> -CH2OC2H5 <SEP> Huile
<tb> TABLEAU II : (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Compound
<tb> n <SEP> R3 <SEP> R5 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> 41 <SEP> H <SEP> -CH3 <SEP>#<SEP> -CH2OCH3 <SEP>#<SEP> - <SEP> 1.5100
<tb> 42 <SEP> 3-CH3 <SEP> -CH3 <SEP> -CHO <SEP> -CH2OCH3 <SEP>#<SEP> = <SEP> 1.5346
<tb> 43 <SEP> H <SEP> -CH3 <SEP> -CH (OCH3) 2 <SEP> -CH2OC3H7-i <SEP> Oil
<tb> 44 <SEP> H <SEP> -C2H5 <SEP> -CH (OCH3) 2 <SEP> -CH2OCH3 <SEP> Viscous
<tb> 45 <SEP> 3-CH3 <SEP> -CH3 <SEP> -CHO <SEP> -CH2OSO2NHCH3 <SEP> Viscous
<tb> 46 <SEP> H <SEP> -CH3 <SEP> -CH (OCH3) 2 <SEP> -CH2OCH2CH = CH2 <SEP> Oil
<tb> 47 <SEP> H <SEP> -C2H5 <SEP> -CH (OCH3) 2 <SEP> -CH2OC2H5 <SEP> Oil
<TABLE> TABLE II: (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Composé
<tb> n <SEP> R3 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> 48 <SEP> H <SEP> # <SEP> # <SEP> Huile
<tb> 49 <SEP> 3-CH3 <SEP> -CH(OCH3)2 <SEP> -CH2OCH3 <SEP> # <SEP> = <SEP> 1,5293
<tb> 50 <SEP> H <SEP> # <SEP> -CH2OC2H5 <SEP> Huile <SEP> visqueuse
<tb> 51 <SEP> H <SEP> -CH(OCH3)2 <SEP> -CH2OCH2C=CH
<tb> 52 <SEP> 3-CH3 <SEP> -CH(OCH3)2 <SEP> -CH2OC2H5 <SEP> # <SEP> = <SEP> 1,5071
<tb> 53 <SEP> H <SEP> # <SEP> -CH2OCH3
<tb> 54 <SEP> H <SEP> -CH(OCH3)2 <SEP> -CH2SCH3
<tb> TABLEAU II : (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Compound
<tb> n <SEP> R3 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> 48 <SEP> H <SEP>#<SEP>#<SEP> Oil
<tb> 49 <SEP> 3-CH3 <SEP> -CH (OCH3) 2 <SEP> -CH2OCH3 <SEP>#<SEP> = <SEP> 1.5293
<tb> 50 <SEP> H <SEP>#<SEP> -CH2OC2H5 <SEP> Viscous <SEP> Oil
<tb> 51 <SEP> H <SEP> -CH (OCH3) 2 <SEP> -CH2OCH2C = CH
<tb> 52 <SEP> 3-CH3 <SEP> -CH (OCH3) 2 <SEP> -CH2OC2H5 <SEP>#<SEP> = <SEP> 1.5071
<tb> 53 <SEP> H <SEP>#<SEP> -CH2OCH3
<tb> 54 <SEP> H <SEP> -CH (OCH3) 2 <SEP> -CH2SCH3
<TABLE> TABLE II: (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Composé <SEP> R3 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> n
<tb> 55 <SEP> H <SEP> -CH(OC4H9-n)2 <SEP> -CH2OCH3
<tb> 56 <SEP> 3-CH3 <SEP> -CH(OCH3)2 <SEP> -CH2OSO2NHCH3
<tb> 57 <SEP> H <SEP> # <SEP> -CH2OCH3 <SEP> Pf <SEP> 63-65
<tb> 58 <SEP> H <SEP> -CH(OCH3)2 <SEP> -CH2NHN(CH3)2
<tb> 59 <SEP> H <SEP> # <SEP> #
<tb> 60 <SEP> H <SEP> -CH(OC3H7-n)2 <SEP> #
<tb> 61 <SEP> H <SEP> -CH(OCH3)2 <SEP> #
<tb> TABLEAU II : (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Compound <SEP> R3 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> n
<tb> 55 <SEP> H <SEP> -CH (OC4H9-n) 2 <SEP> -CH2OCH3
<tb> 56 <SEP> 3-CH3 <SEP> -CH (OCH3) 2 <SEP> -CH2OSO2NHCH3
<tb> 57 <SEP> H <SEP>#<SEP> -CH2OCH3 <SEP> Pf <SEP> 63-65
<tb> 58 <SEP> H <SEP> -CH (OCH3) 2 <SEP> -CH2NHN (CH3) 2
<tb> 59 <SEP> H <SEP>#<SEP>#
<tb> 60 <SEP> H <SEP> -CH (OC3H7-n) 2 <SEP>#
<tb> 61 <SEP> H <SEP> -CH (OCH3) 2 <SEP>#
<TABLE> TABLE II: (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Composé <SEP> R3 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> n
<tb> 62 <SEP> H <SEP> # <SEP> -CH2OCH3
<tb> 63 <SEP> H <SEP> # <SEP> -CH2OC2H5
<tb> 64 <SEP> H <SEP> -CH(OCH3)2 <SEP> -CH2OSO2CH3
<tb> 65 <SEP> 3-CH3 <SEP> # <SEP> -OH2OCH3 <SEP> n13 <SEP> = <SEP> 1,5328
<tb> 66 <SEP> H <SEP> -CH(OC3H7-n)2 <SEP> -CH2OCH3
<tb> 67 <SEP> 3-CH3 <SEP> # <SEP> # <SEP> Huile
<tb> 68 <SEP> H <SEP> -CH(OC3H7-i)2 <SEP> -CH2OC2H5
<tb> TABLEAU II : (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Compound <SEP> R3 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> n
<tb> 62 <SEP> H <SEP>#<SEP> -CH2OCH3
<tb> 63 <SEP> H <SEP>#<SEP> -CH2OC2H5
<tb> 64 <SEP> H <SEP> -CH (OCH3) 2 <SEP> -CH2OSO2CH3
<tb> 65 <SEP> 3-CH3 <SEP>#<SEP> -OH2OCH3 <SEP> n13 <SEP> = <SEP> 1.5328
<tb> 66 <SEP> H <SEP> -CH (OC3H7-n) 2 <SEP> -CH2OCH3
<tb> 67 <SEP> 3-CH3 <SEP>#<SEP>#<SEP> Oil
<tb> 68 <SEP> H <SEP> -CH (OC3H7-i) 2 <SEP> -CH2OC2H5
<TABLE> TABLE II: (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Composé <SEP> R3 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> n
<tb> 69 <SEP> H <SEP> # <SEP> -CH2OCH3 <SEP> Pf <SEP> 80-83
<tb> 70 <SEP> H <SEP> # <SEP> #
<tb> 71 <SEP> H <SEP> -CH(OCH3)2 <SEP> -CH2OSO2C2H5 <SEP> Huile
<tb> 72 <SEP> 3-CH3 <SEP> # <SEP> -CH2OCH3
<tb> 73 <SEP> H <SEP> -CH(OC3H7-i)2 <SEP> # <SEP> Visqueux
<tb> 74 <SEP> 3-Cl <SEP> -CH(OCH3)2 <SEP> -CH2OC2H5
<tb> TABLEAU II : (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Compound <SEP> R3 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> n
<tb> 69 <SEP> H <SEP>#<SEP> -CH2OCH3 <SEP> Pf <SEP> 80-83
<tb> 70 <SEP> H <SEP>#<SEP>#
<tb> 71 <SEP> H <SEP> -CH (OCH3) 2 <SEP> -CH2OSO2C2H5 <SEP> Oil
<tb> 72 <SEP> 3-CH3 <SEP>#<SEP> -CH2OCH3
<tb> 73 <SEP> H <SEP> -CH (OC3H7-i) 2 <SEP>#<SEP> Viscous
<tb> 74 <SEP> 3-Cl <SEP> -CH (OCH3) 2 <SEP> -CH2OC2H5
<TABLE> TABLE II: (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Composé <SEP> R3 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> n
<tb> 75 <SEP> H <SEP> # <SEP> -CH2OCH3 <SEP> Pf <SEP> 55,5-57
<tb> 76 <SEP> H <SEP> -CH(OCH3)2 <SEP> -CH2OCCH3
<tb> <SEP> O
<tb> 77 <SEP> 3-Cl <SEP> # <SEP> -CH2OCH3
<tb> 78 <SEP> H <SEP> -CH(OC2H5)2 <SEP> #
<tb> 79 <SEP> 3-CH3 <SEP> # <SEP> -CH2OC2H5
<tb> 80 <SEP> H <SEP> # <SEP> -CH2OSO2NHCH3
<tb> TABLEAU II : (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Compound <SEP> R3 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> n
<tb> 75 <SEP> H <SEP>#<SEP> -CH2OCH3 <SEP> Pf <SEP> 55,5-57
<tb> 76 <SEP> H <SEP> -CH (OCH3) 2 <SEP> -CH2OCCH3
<tb><SEP> O
<tb> 77 <SEP> 3-Cl <SEP>#<SEP> -CH2OCH3
<tb> 78 <SEP> H <SEP> -CH (OC2H5) 2 <SEP>#
<tb> 79 <SEP> 3-CH3 <SEP>#<SEP> -CH2OC2H5
<tb> 80 <SEP> H <SEP>#<SEP> -CH2OSO2NHCH3
<TABLE> TABLE II: (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Composé <SEP> R3 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> n
<tb> 81 <SEP> H <SEP> -CH(OC2H5)2 <SEP> #
<tb> 82 <SEP> 3-CH3 <SEP> # <SEP> CH2OCH3
<tb> 83 <SEP> H <SEP> -CH(OC3H7-i)2 <SEP> #
<tb> 84 <SEP> H <SEP> # <SEP> -CH2OCH3 <SEP> n25 <SEP> = <SEP> 1,5123
<tb> 85 <SEP> H <SEP> -CH(OC2H5)2 <SEP> -CH2CH2OCH3
<tb> 86 <SEP> 3-CH3 <SEP> # <SEP> -CH2OSO2NHCH3
<tb> 87 <SEP> H <SEP> # <SEP> -CH2OCH3 <SEP> Pf <SEP> 96,5-97,5%
<tb> TABLEAU II : (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Compound <SEP> R3 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> n
<tb> 81 <SEP> H <SEP> -CH (OC2H5) 2 <SEP>#
<tb> 82 <SEP> 3-CH3 <SEP>#<SEP> CH2OCH3
<tb> 83 <SEP> H <SEP> -CH (OC3H7-i) 2 <SEP>#
<tb> 84 <SEP> H <SEP>#<SEP> -CH2OCH3 <SEP> n25 <SEP> = <SEP> 1.5123
<tb> 85 <SEP> H <SEP> -CH (OC2H5) 2 <SEP> -CH2CH2OCH3
<tb> 86 <SEP> 3-CH3 <SEP>#<SEP> -CH2OSO2NHCH3
<tb> 87 <SEP> H <SEP>#<SEP> -CH2OCH3 <SEP> Pf <SEP> 96.5-97.5%
<TABLE> TABLE II: (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Composé <SEP> R3 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> n
<tb> 88 <SEP> H <SEP> -CH(OC2H5)2 <SEP> -CH2OCH3
<tb> 89 <SEP> H <SEP> # <SEP> -CH2OC2H5 <SEP> Pf <SEP> 87-90 C
<tb> 90 <SEP> 3-CH3 <SEP> # <SEP> -CH2OC2H5
<tb> 91 <SEP> H <SEP> -CH(OC3H7-i)2 <SEP> #
<tb> 92 <SEP> 3-CH3 <SEP> # <SEP> -CH2OC2H5
<tb> 93 <SEP> 3-Cl <SEP> -CH(OCH3)2 <SEP> -CH2OSO2NHCH3
<tb> 94 <SEP> H <SEP> -CH(OC3H7i)2 <SEP> -CH2OCH3
<tb> TABLEAU II : (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Compound <SEP> R3 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> n
<tb> 88 <SEP> H <SEP> -CH (OC2H5) 2 <SEP> -CH2OCH3
<tb> 89 <SEP> H <SEP>#<SEP> -CH2OC2H5 <SEP> Pf <SEP> 87-90C
<tb> 90 <SEP> 3-CH3 <SEP>#<SEP> -CH2OC2H5
<tb> 91 <SEP> H <SEP> -CH (OC3H7-i) 2 <SEP>#
<tb> 92 <SEP> 3-CH3 <SEP>#<SEP> -CH2OC2H5
<tb> 93 <SEP> 3-Cl <SEP> -CH (OCH3) 2 <SEP> -CH2OSO2NHCH3
<tb> 94 <SEP> H <SEP> -CH (OC3H7i) 2 <SEP> -CH2OCH3
<TABLE> TABLE II: (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Composé <SEP> R3 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> n
<tb> <SEP> 95 <SEP> H <SEP> # <SEP> -CH2OCH3
<tb> <SEP> 96 <SEP> 3-CH3 <SEP> -CHO <SEP> # <SEP> n26 <SEP> 1,5396
<tb> <SEP> 97 <SEP> 3-Cl <SEP> # <SEP> -CH2OCH3 <SEP> Huile
<tb> <SEP> 98 <SEP> 3-Cl <SEP> -CH(OCH3)2 <SEP> -CH2OCH3 <SEP> Huile
<tb> <SEP> 99 <SEP> H <SEP> # <SEP> -CH2OCH3
<tb> 100 <SEP> H <SEP> -CH(OCH3)2 <SEP> -CH2OSO2NHCH3 <SEP> Huile
<tb> TABLEAU II : (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Compound <SEP> R3 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> n
<tb><SEP> 95 <SEP> H <SEP>#<SEP> -CH2OCH3
<tb><SEP> 96 <SEP> 3-CH3 <SEP> -CHO <SEP>#<SEP> n26 <SEP> 1.5396
<tb><SEP> 97 <SEP> 3-Cl <SEP>#<SEP> -CH2OCH3 <SEP> Oil
<tb><SEP> 98 <SEP> 3-Cl <SEP> -CH (OCH3) 2 <SEP> -CH2OCH3 <SEP> Oil
<tb><SEP> 99 <SEP> H <SEP>#<SEP> -CH2OCH3
<tb> 100 <SEP> H <SEP> -CH (OCH3) 2 <SEP> -CH2OSO2NHCH3 <SEP> Oil
<TABLE> TABLE II: (R1 = CH3, R2 = CH3, R4 = H, R5 = CH3)
Composé <SEP> R3 <SEP> X <SEP> R6 <SEP> Constantes <SEP> physiques
<tb> n
<tb> 101 <SEP> H <SEP> # <SEP> -CH2OSO2NHCH3
<tb> 102 <SEP> H <SEP> # <SEP> -CH2OCH3
<tb> 103 <SEP> H <SEP> -CH(OC2H5)2 <SEP> -CH2OC2H5 <SEP> Huile
<tb> 104 <SEP> 3-CH3 <SEP> # <SEP> -CH2OCH3 <SEP> Pf <SEP> 76-78
<tb> 105 <SEP> 3-CH3 <SEP> # <SEP> -CH2OCH3 <SEP> n13 <SEP> 1,5239
<tb> 106 <SEP> 3-CH3 <SEP> # <SEP> -CH2OCH3 <SEP> n25 <SEP> 1,5118
<tb>
TABLEAU III : (R1 = CH3, R3 =H, R4 =H, R5 = CH3)
Compound <SEP> R3 <SEP> X <SEP> R6 <SEP> Physical <SEP> Constants
<tb> n
<tb> 101 <SEP> H <SEP>#<SEP> -CH2OSO2NHCH3
<tb> 102 <SEP> H <SEP>#<SEP> -CH2OCH3
<tb> 103 <SEP> H <SEP> -CH (OC2H5) 2 <SEP> -CH2OC2H5 <SEP> Oil
<tb> 104 <SEP> 3-CH3 <SEP>#<SEP> -CH2OCH3 <SEP> Pf <SEP> 76-78
<tb> 105 <SEP> 3-CH3 <SEP>#<SEP> -CH2OCH3 <SEP> n13 <SEP> 1.5239
<tb> 106 <SEP> 3-CH3 <SEP>#<SEP> -CH2OCH3 <SEP> n25 <SEP> 1.5118
<Tb>
TABLE III: (R1 = CH3, R3 = H, R4 = H, R5 = CH3)
<tb> composé <SEP> R2 <SEP> x <SEP> B <SEP> R6
<tb> 107 <SEP> Cl <SEP> | <SEP> -CH(OCH3 <SEP> )2 <SEP> -CH,OCR,
<tb> <SEP> 108 <SEP> C2H5 <SEP> sUX <SEP> 02H5 <SEP> -CH20O5
<tb> <SEP> V21-L5 <SEP> ~H
<tb> 109 <SEP> Cl <SEP> -CH(0CE5)2 <SEP> -CH20CH3
<tb> <SEP> 110 <SEP> a2H5 <SEP> -CH
<tb> <SEP> CH <SEP> 5 <SEP> -CH
<tb> <SEP> 111 <SEP> C5 <SEP> -CH(oCH3)2 <SEP> -CH20C5
<tb> 112 <SEP> C1 <SEP> / <SEP> /0 <SEP> -CH
<tb> <SEP> - <SEP> -CH2OCH3
<tb> <SEP> 113 <SEP> CtE5 <SEP> -CH <SEP> (OCE3 <SEP> )2 <SEP> -cH2OCH3
<tb> <SEP> L3 <SEP> 2
<tb> 114 <SEP> C2Hs <SEP> - <SEP> o X1 <SEP> -CH20CH3
<tb> 115 <SEP> Cl <SEP> C2Ns <SEP> i <SEP> -CH20CH3
<tb> <SEP> CJf <SEP>
<SEP> 116 <SEP> C2H5 <SEP> -CH <SEP> T <SEP> t <SEP> 5 <SEP> -CF-2oCH3
<tb> <SEP> 117 <SEP> 0CH3 <SEP> /0 <SEP> C2Hs <SEP> -CH20CH3
<tb> 118 <SEP> Cl <SEP> -CH0CH
<tb> <SEP> CNH0
<tb>
TABLEAU III : (R1 = CH3, R3 = H, R4 = H, R5 = CH3)
<tb> compound <SEP> R2 <SEP> x <SEP> B <SEP> R6
<tb> 107 <SEP> Cl <SEP> | <SEP> -CH (OCH3 <SEP>) 2 <SEP> -CH, OCR,
<tb><SEP> 108 <SEP> C2H5 <SEP> sUX <SEP> 02H5 <SEP> -CH20O5
<tb><SEP> V21-L5 <SEP> ~ H
<tb> 109 <SEP> Cl <SEP> -CH (0CE5) 2 <SEP> -CH20CH3
<tb><SEP> 110 <SEP> a2H5 <SEP> -CH
<tb><SEP> CH <SEP> 5 <SEP> -CH
<tb><SEP> 111 <SEP> C5 <SEP> -CH (oCH3) 2 <SEP> -CH20C5
<tb> 112 <SEP> C1 <SEP> / <SEP> / 0 <SEP> -CH
<tb><SEP> - <SEP> -CH2OCH3
<tb><SEP> 113 <SEP> CtE5 <SEP> -CH <SEP> (OCE3 <SEP>) 2 <SEP> -cH2OCH3
<tb><SEP> L3 <SEP> 2
<tb> 114 <SEP> C2Hs <SEP> - <SEP> o X1 <SEP> -CH20CH3
<tb> 115 <SEP> Cl <SEP> C2Ns <SEP> i <SEP> -CH20CH3
<tb><SEP> CJf <SEP>
<SEP> 116 <SEQ> C2H5 <SEP> -CH <SEP> T <SEP> t <SEP> 5 <SEP> -CF-2oCH3
<tb><SEP> 117 <SEP> 0CH3 <SEP> / 0 <SEP> C2Hs <SEP> -CH20CH3
<tb> 118 <SEP> Cl <SEP> -CHOCH
<tb><SEP> CNH0
<Tb>
TABLE III: (R1 = CH3, R3 = H, R4 = H, R5 = CH3)
<tb> Gçnposé <SEP> R <SEP> X <SEP> R6
<tb> <SEP> : <SEP> - <SEP> A
<tb> <SEP> 119 <SEP> 0CH3 <SEP> -CH(0CH-3) <SEP> -CH-20CH3
<tb> -OR200113
<tb> <SEP> 120 <SEP> QCX3 <SEP> -Cs <SEP> \ <SEP> -CE20CH3
<tb>
TABLEAU IV : (R1 = CH3, R2 = CH3, R3 = 3-CH3,
R4 = 5-CH3, R5 = CH3)
<tb> Installed <SEP> R <SEP> X <SEP> R6
<tb><SEP>:<SEP> - <SEP> A
<tb><SEP> 119 <SEP> 0CH3 <SEP> -CH (0CH-3) <SEP> -CH-20CH3
<tb> -OR200113
<tb><SEP> 120 <SEQ> QCX3 <SEP> -Cs <SEP> \ <SEP> -CE20CH3
<Tb>
TABLE IV: (R1 = CH3, R2 = CH3, R3 = 3-CH3,
R4 = 5-CH3, R5 = CH3)
<tb> CQt <SEP> csé <SEP> | <SEP> sr <SEP> 26
<tb> <SEP> - <SEP> / <SEP> Ca5 <SEP> -Fu-oci <SEP> T3
<tb> <SEP> 0
<tb> <SEP> 12e <SEP> .-/o <SEP> -CH20S02rCH3
<tb> <SEP> a <SEP> O <SEP> I <SEP> C2h5 <SEP> -CF0CLt5
<tb> É1!111À132
<tb> <SEP> l11-CÉi(oCH3 <SEP> 2
<tb> <SEP> 3r
<tb> <SEP> 126 <SEP> -C(OCIi,)2
<tb> <SEP> - <SEP> W <SEP> l <SEP> : <SEP> - <SEP>
<tb> 1r7 <SEP> -S?-( <SEP> Oï(0CR3,)2
<tb> <SEP> 0
<tb> <SEP> 128 <SEP> < .<SEP> -Cr-.2002r5
<tb> i <SEP> 0
<tb>
Exemples de formulation
Exemple 5 : Produits pour poudrage
rOUr préparer un produit pour poudrage a) à 5 C' et b) à 2 % on utilise les produits suivants: a) 5 tarties de matière active n 1-128
95 parties de talc b) 2 parties de matière active n 1-128
1 partie d'acide silicique finement div
97 parties de tale;
On mélange et on brois les ratières@ active avec les supports et on peut les appliquer par pou drage sous cette forme.<tb> CQt <SEP> csed <SEP> | <SEP> sr <SEP> 26
<tb><SEP> - <SEP> / <SEP> Ca5 <SEP> -Fu-oci <SEP> T3
<tb><SEP> 0
<tb><SEP> 12th <SEP> .- / o <SEP> -CH20S02rCH3
<tb><SEP> a <SEP> O <SEP> I <SEP> C2h5 <SEP> -CF0CLt5
<tb> É1! 111À132
<tb><SEP> l11-CEi (oCH3 <SEP> 2
<tb><SEP> 3r
<tb><SEP> 126 <SEP> -C (OCIi,) 2
<tb><SEP> - <SEP> W <SEP> l <SEP>: <SEP> - <SEP>
<tb> 1r7 <SEP> -S? - (<SEP> OI (0CR3,) 2
<tb><SEP> 0
<tb><SEP> 128 <SEP><.<SEP> -Cr-.2002r5
<tb> i <SEP> 0
<Tb>
Examples of formulation
Example 5: Products for dusting
To prepare a dusting product a) at 5 ° C and b) at 2% the following products are used: a) 5 tarties of active ingredient n 1-128
95 parts talcum b) 2 parts active ingredient n 1-128
1 part of finely divided silicic acid
97 parts of tale;
The active dies are mixed and ground with the supports and can be applied by dropping in this form.
Exemple 6 : Granulé
Pour préparer un granulé à 5 % en utilise le produits suivants :
5 parties de matière active n 2
0,25 partie d'huile végétale époxydée
0,25 partie de cétylpolyglycoléther
3,50 partie de polyéthylèneglycol
91 parties de @aolin (granulo@étrie 0,3-0,8
mm).Example 6 Granulated
To prepare a 5% granulate using the following products:
5 parts of active ingredient n 2
0.25 parts of epoxidized vegetable oil
0.25 part of cetylpolyglycolether
3.50 part of polyethylene glycol
91 parts of @aolin (granulo @ release 0,3-0,8
mm).
On mélange la matière active avec l'huile végétale époxydée et on la dissout avec 6 parties d'acétone, puis on ajoute le polyethylèneglycol et le cétylpolyglycoléther. On pulvérise la solution ainsi obtenue sur le kaolin, puis on fait évaporer l'acétone sous vide. On a avantage à utiliser un microgranulé de ce type pour lutter contre les champignons du sol. The active ingredient is mixed with the epoxidized vegetable oil and dissolved with 6 parts of acetone, and then polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed on the kaolin, and the acetone is evaporated under vacuum. It is advantageous to use a microgranule of this type for controlling soil fungi.
Exemple 7 : Poudres mouillables
Pour préparer une poudre mouillable a) à 70 %, b) à 40 %, c) et d) à 25 % et e) à 10 % on utilise les composants suivants a) 70 parties de matière active n 1-128
5 parties de dibutylnaphtylsulfonate de sodium
3 parties de condensat acides naphtalène
sulfoniques-acides phénolsulfoniques formaldéhyde (3:2:1)
10 parties de kaolin
12 parties de craie de Champagne; b) 40 parties de matière active n0 1-128
5 parties de sel de sodium de l'acide
ligninesulfonique
1 partie de sel de sodium de l'acide di butylnaphtal è ne s ulfo ni que
54 parties d'acide silicique; c) 25 parties de matière active n 2
4,5 parties de ligninesulfonate de calcium
1,9 partie d'un mélange craie de Champagne/
hydroxyéthylcellulose (1:1)
1,5 partie de dibutylnaphtalènesulfonate de
sodium
19,5 parties d'acide silicique
19,5 parties de craie de Champagne
28,1 parties de kaolin; d) 25 parties de matière active n 42
2,5 parties d'isoctylphénoxy-polyoxyéthylène
éthanol
1,7 partie de mélange craie de Champagne/
hydroxyéthylcellulose (1:1)
8,3 parties de silicate de sodiumaluminium
16,5 parties de kieselgur
46 parties de kaolin e) 10 parties de matière active n 2
3 parties du mélange des sels de sodium de
sulfates d'alcools gras saturés
5 parties de condensat acide nanhtalènesul- fonique /formaldé hyde
82 parties de kaolin. Example 7: Wettable powders
To prepare a wettable powder a) at 70%, b) at 40%, c) and d) at 25% and e) at 10% the following components are used: a) 70 parts of active ingredient n 1-128
5 parts of sodium dibutylnaphthylsulfonate
3 parts condensate naphthalene acids
sulfonic acid phenolsulfonic acid formaldehyde (3: 2: 1)
10 parts of kaolin
12 parts of Champagne chalk; (b) 40 parts of active ingredient n0 1-128
5 parts of sodium salt of the acid
ligninsulfonic
1 part of sodium salt of di butylnaphthalic acid is only
54 parts of silicic acid; (c) 25 parts of active ingredient 2
4.5 parts of calcium ligninsulfonate
1.9 part of a chalk mixture of Champagne /
hydroxyethylcellulose (1: 1)
1.5 parts of dibutylnaphthalenesulphonate
sodium
19.5 parts of silicic acid
19.5 parts of chalk of Champagne
28.1 parts of kaolin; (d) 25 parts of active ingredient n 42
2.5 parts of isoctylphenoxypolyoxyethylene
ethanol
1.7 parts of Champagne chalk mix /
hydroxyethylcellulose (1: 1)
8.3 parts of sodium aluminum silicate
16.5 parts of kieselgur
46 parts of kaolin e) 10 parts of active ingredient n 2
3 parts of the mixture of the sodium salts of
saturated fatty alcohol sulphates
5 parts of naphthalenesulfonic acid / formaldehyde condensate
82 parts of kaolin.
On mélange intimenent les matières actives avec les additifs dans des mélangeurs appropriés et on les broie dans des moulins et des cylindres correspondants. On obtient une poudre mouillable d'excellentes mouillabilité et flottabilité, que l'on peut diluer avec de l'eau pour obtenir des suspensions ayant la concentration voulue et que l'on peut utiliser en particulier par application sur les feuilles. The active ingredients are intimately mixed with the additives in suitable mixers and ground in corresponding mills and rolls. A wettable powder of excellent wettability and buoyancy is obtained, which can be diluted with water to obtain suspensions having the desired concentration and which can be used in particular by application to the leaves.
Exemple 8 : Concentrés émulsifiables
Pour préparer un concentré émulsifiable à 25 %, on utilise les produits suivants
25 parties de matière active n 2 ou d'une
autre de formule
2,5 parties d'huile végétale épo,zydée
10 parties d'un mélange alcoylarylsulfo
nate/polyglycoléther d'alcool gras
5 parties de diméthylformamide
57,5 parties de xylène.Example 8 Emulsifiable Concentrates
To prepare a 25% emulsifiable concentrate, the following products are used:
25 parts of active ingredient n 2 or one
other of formula
2.5 parts of vegetable oil epo, zydée
10 parts of an alkylaryl sulfo mixture
fatty alcohol nate / polyglycol ether
5 parts of dimethylformamide
57.5 parts of xylene.
A partir de tels concentrés, on peut préparer par dilution avec de l'eau des émulsions ayant la concentration d'application désirée, particulièrement appropriées à l'application sur les feuilles. From such concentrates, emulsions having the desired application concentration, particularly suitable for application to the sheets, can be prepared by dilution with water.
Exemples biologiques
ExemPle 9 : Action contre Phytophthora infestais sur
les plants de tomates a) Action protectrice résiduelle
Après les avoir cultivés pendant 3 semaines, on pulvérise sur des plants de tomates une bouillie de pulvérisation (0,06 Ci' de matière active) préparée à partir d'une poudre mouillable de la matière active.Biological examples
EXAMPLE 9: Action against Phytophthora infesting on
tomato plants a) Residual protective action
After cultivation for 3 weeks, tomato plants are sprayed with a spray mixture (0.06 Ci of active ingredient) prepared from a wettable powder of the active ingredient.
Au bout de 24 heures on infeste les plants traités avec une suspension de sporanges du champignon. La détermination de l'infestation par les champignons s'effectue après une incubation des plants infestés pendant 5 jours à 90-100 f d'humidité relative et à 20 C. After 24 hours, the treated plants are infested with a suspension of sporangia of the fungus. Fungi infestation is determined after incubation of the infested plants for 5 days at 90-100% relative humidity and 20C.
b) Action résiduelle curative
après les avoir cultivés pendant 3 semaines on infeste des plants ae tomate avec une suspension de sporanges du champignon. Après un temps d'incubation de @2 heures en chambre humide à 90-100 % d'hunidité relative et à 20 C, on sèche les plants infestés sur lesquels on pulvérise ensuite une bouillie de pulvérisation (0,06 % de matière active0 préparée à partir d'une poudre mouillable de la matière active.b) Remaining curative action
after having cultivated them for 3 weeks, tomato plants were infested with a suspension of sporangia of the fungus. After an incubation period of 2 hours in a 90-100% relative humidity and 20 C wet chamber, the infested plants are dried on which a spray slurry is then sprayed (0.06% prepared active ingredient). from a wettable powder of the active ingredient.
Après @é@lage du dépôt de pulvérisation on transfère à nouveau les plants traités en chambre humide. La détermination de l'infestation par les champignons s'effectue 5 jours après l'infestation. After spraying, the treated plants are again transferred to a humid chamber. The fungus infestation is determined 5 days after the infestation.
c) Action systémique
Sur ces plants de tomates que l'on a cultivés pondant 3 semaines on verse une bouillie de pulvérisation préparée à tartir d'une poudre mouillable de la matière active (0,006 % de matière active par rapport au volume de terre). On veille dans cette operation à ce çw-- la bouillie de pulvérisation n'entre pas en contact avec les parties aériennes des plantes. Au bout de 48 heures on infecte les plants traités avec une suspension de sporanges du champignon. La détermination @@ l'infestation par les champignons s'effectue après une incubation des plants traités pendant 5 jours à 90-100 % d'humidité relative et à 20 C.c) Systemic action
On these tomato plants which have been grown for 3 weeks, a spray mixture prepared from a wettable powder of the active ingredient (0.006% of active substance relative to the volume of soil) is poured. In this operation, care is taken to ensure that the spray mixture does not come into contact with the aerial parts of the plants. After 48 hours the treated plants were infected with sporangia suspension of the fungus. The fungal infestation is determined after incubation of the treated plants for 5 days at 90-100% relative humidity and 20 C.
Exemple 10
Action contre plasmopara viticola sur la vigne
On pulvérise sur des ceps de vigne au stade 4 5 feuilles une bouillie de pulvérisation (0,06 % de matière active) préparée à partir d'une poudre mouillable de la matière active. Au bout de 24 heures on infeste les plants traités avec une suspension de sporanges du champignon. Après incubation pendant 6 jours à 95-100 % d'humidité relative et à 20 C, on détermine l'infestation par les champignons. Example 10
Action against plasmopara viticola on the vine
Vines in the 45 leaf stage are sprayed with a spray mixture (0.06% active ingredient) prepared from a wettable powder of the active ingredient. After 24 hours, the treated plants are infested with a suspension of sporangia of the fungus. After incubation for 6 days at 95-100% relative humidity and 20 C, the infestation with fungi is determined.
exemple 11 Action contre Pythium debaryanum sur les raves
Action après application au sol
On cultive le champignon sur une solution nutritive de rondelles de carottes et on l'introduit dans un mélange de terre et de sable. On répartit la terre ainsi infestée dans des pots de fleurs et on y sème des graines de betterave. Immédiatement après l'ensemencement on verse sur la terre les préparatio expérimentales, formulées en poudres mouillables. @@ forme de suspensions aqueuses (20 ppm de matière active par rapport au volume de terre). Cn dispose en- suite les pots pendant 2 à 3 semaine nes en serre a en- viron 20 C.On maintient alors la terre toujours régulièrement humide en arrosant légèrement.example 11 Action against Pythium debaryanum on raves
Action after ground application
The mushroom is grown on a nutrient solution of carrot slices and introduced into a mixture of soil and sand. The soil thus infested is divided into flowerpots, and beet seed is sown. Immediately after seeding, experimental preparations are poured onto the soil, formulated as wettable powders. form of aqueous suspensions (20 ppm of active ingredient relative to the volume of soil). The pots are then left for 2 to 3 weeks in a greenhouse at about 20 ° C. The soil is then kept moist and watered.
Lors de l'évaluation de l'expérience, on détermine la levée des plants de betterave ainsi que la fraction de plants sains et malades
Action après application désinfectante
On cultive le champignon sur une solution nutritive de rondelles de carottes et on l'introduit dans un mélange de terre et ce sable. On répartit la terre ainsi infestée dans des bacs de terre que l'on ensemence avec des graines de betterave pré@@ablement désinfectées avec les préparations expérimentales for mulées en poudre désinfectante 90,06 % de matière active).During the evaluation of the experiment, the emergence of beet plants and the fraction of healthy and sick plants are determined.
Action after disinfectant application
The mushroom is grown on a nutrient solution of carrot slices and introduced into a mixture of soil and sand. The soil thus infested is distributed in earthen tanks which are seeded with beet seeds pre-disinfected with the experimental preparations for powdered disinfectant (90.06% active ingredient).
On dispose les pots ensemencés pendant 2 à 3 semaines en serre à environ 20 C. On naintier- ' a terre toujours régulièrement humide en arrosant légèrement. Lors de l'évaluation on détermine la levée des plants de betterave. The seeded pots are placed for 2 to 3 weeks in a greenhouse at about 20 ° C. The soil is regularly moistened by gentle spraying. During the evaluation, the emergence of the beet plants is determined.
exemple 12
Action contre Venturia inaequalis sur le pommier
Action protectrice résiduelle
On pulvérise sur des pommiers de semis ayant environ 5 feuilles développées une bouillie de pulvérisation (0,06 /0 de matière active) préparée à partir d'une poudre mouillable de la matière active. Au bout de 24 heures on infeste les plants traités avec une suspension de conidies du champignon. On fait incuber alors les plants pendant 5 jours à 90-100 ,'^ d'humidi- té relative et on les dispose pendant 10 jours de plus en serre à 20-24 C. On détermine l'incidence de la tavelure 15 jours après l'infestation.example 12
Action against Venturia inaequalis on the apple tree
Residual protective action
Seed apple trees having about 5 developed leaves are sprayed with a spray mixture (0.06% active ingredient) prepared from a wettable powder of the active ingredient. After 24 hours, the treated plants are infested with a suspension of conidia of the fungus. The plants are then incubated for 5 days at 90-100 wt. Of relative humidity and placed for an additional 10 days in a greenhouse at 20-24 C. The incidence of scab is determined 15 days later. the infestation.
Exemple 13
Action contre Cercospora arachidicola sur les arachides
Action Protectrice résiduelle
On pulvérise sur des plants d'arachide de 10 à 15 cm de haut une bouillie de pulvérisation (0,02 ss de matière active) préparée à partir d'une poudre mouillable de la matière active et on les infeste 48 heures plus tard avec une suspension de conidies du champignon. On incube les plants infestés pendant 72 heures à environ 2100 et sous une atmosphère très humide puis on les dispose en serre jusqu'à l'appari- tion des taches typiques sur les feuilles. La détermination de l'action fongicide s1 effectue 12 jours après l'infestation d'après le nombre et la taille des taches apparues.Example 13
Action against Cercospora arachidicola on peanuts
Residual Protective Action
Peanut plants 10-15 cm high were sprayed with a spray mixture (0.02 μs active ingredient) prepared from a wettable powder of the active ingredient and infested 48 hours later with suspension of conidia of the fungus. The infested plants are incubated for 72 hours at about 2100 and in a very humid atmosphere, and then placed in the greenhouse until the typical leaf spots appear. The determination of the fungicidal action takes place 12 days after the infestation according to the number and the size of the spots appeared.
Dans les expériences des exemples 9, 10, 11, 12 et 13, les composés de formule I présentent une forte action fongicide (incidence de la maladie inférieure à 25 ). On obtient une inhibition complète de la maladie avec les préparations suivantes
Exemple 9 : Composés n0 2, 3, 10, 42, 49, 65;
Exemple 10 : Composés n 2, 3, 42;
Exemple 11 : Composés n 2, 10, 65;
Exemple 12 : Composé n 2. In the experiments of Examples 9, 10, 11, 12 and 13, the compounds of formula I exhibit a strong fungicidal action (incidence of the disease less than 25). Complete inhibition of the disease is achieved with the following preparations
Example 9: Compounds Nos. 2, 3, 10, 42, 49, 65;
Example 10: Compounds Nos. 2, 3, 42;
Example 11: Compounds No. 2, 10, 65;
Example 12: Compound No. 2
Claims (12)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH638479 | 1979-07-09 |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2465711A1 true FR2465711A1 (en) | 1981-03-27 |
FR2465711B1 FR2465711B1 (en) | 1983-09-23 |
Family
ID=4308729
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR8015077A Granted FR2465711A1 (en) | 1979-07-09 | 1980-07-07 | Systemic fungicide 2-N-phenyl-acylamino-acetaldehyde derivs. - prepd. e.g. by reaction of halo-acetaldehyde cpds. with N-acyl-aniline cpds., useful against phytophthora and pythium |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE3025694A1 (en) |
FR (1) | FR2465711A1 (en) |
IT (1) | IT8023309A0 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3101785A1 (en) * | 1981-01-21 | 1982-08-26 | Bayer Ag, 5090 Leverkusen | N-SUBSTITUTED ANILIDES, METHODS FOR THEIR PRODUCTION AND THEIR USE AS FUNGICIDES |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2217328A1 (en) * | 1973-02-12 | 1974-09-06 | Velsicol Chemical Corp | Herbicidal anilides - N-alpha-haloacyl-N-(O-and/or S-contg heterocyclyl-(m)ethyl) -2-alkyl-aniline derivs |
-
1980
- 1980-07-07 FR FR8015077A patent/FR2465711A1/en active Granted
- 1980-07-07 DE DE19803025694 patent/DE3025694A1/en not_active Withdrawn
- 1980-07-08 IT IT8023309A patent/IT8023309A0/en unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2217328A1 (en) * | 1973-02-12 | 1974-09-06 | Velsicol Chemical Corp | Herbicidal anilides - N-alpha-haloacyl-N-(O-and/or S-contg heterocyclyl-(m)ethyl) -2-alkyl-aniline derivs |
Also Published As
Publication number | Publication date |
---|---|
FR2465711B1 (en) | 1983-09-23 |
DE3025694A1 (en) | 1981-01-29 |
IT8023309A0 (en) | 1980-07-08 |
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