LU84295A1 - Procede de preparation d'acides phenoxybenzoiques - Google Patents

Procede de preparation d'acides phenoxybenzoiques Download PDF

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LU84295A1
LU84295A1 LU84295A LU84295A LU84295A1 LU 84295 A1 LU84295 A1 LU 84295A1 LU 84295 A LU84295 A LU 84295A LU 84295 A LU84295 A LU 84295A LU 84295 A1 LU84295 A1 LU 84295A1
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Luxembourg
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atoms
formula
group
temperature
eue
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LU84295A
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El-Ahmadi I Heiba
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Rhone Poulenc Agrochimie
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    • 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
    • A01N1/00—Preservation of bodies of humans or animals, or parts thereof
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    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
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    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
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    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
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    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
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    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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Description

La présente invention concerne un procécé perfectionné ce préparation ce certains cérivés c'acices phénoxy-benzoïques à croupe sulfcnamic.e ayant ces propriétés herbi-cices.
5 Des cérivés hercicices c'acïres phéncxybenzoioues è groupe sulfonsmioe sont connus es ns les cernantes ce brevets européens 3£it et 23352.
Ces cemances ce brevets civuiguent ces produits ce formule : lu
C ,B R
y-/ _/ 0 Vy s (I)
E ' X F
13 et leurs sels, dans laquelle : A est 1’hycroçère, le fluor, le chlore, le brome, l'ioce, un groupe nitre; -K-NCF, ; PCLH et <ses esters c'sl-
S Z
2C kyle ce 1 à A atomes de carbone ; N FU, NHOH, N* ; un -groupe csrbcxyle ou l'un ce ses cérivés fonctionnels ; un groupe monoou cislkylaminc ; un groupe NH-CD-R·*" dans le- l quel R est ur, radical alkyle ou alkoxyle ou moncslkyls-mino ou cialkyiamino ; un groupe alkyle ; trialkylammonio, 25 NHS0,.Rz où r. est un racical alkyle ou phényle ; L· r r* NHCLkt-.Sü^n , où h*· a la signification céjà indiquée, sikylthio, alkylsulfinyie, alkyisuifenyie, cielkylsul-fonio, cyancsulfonyle, hycroxy, alkanoyloxy, alkoxy, alkoxy substitué pai un slkoxycerbcnyle, SH, nitrcsc, -SCN, szide, 3u CF-., -N=!«-P- ( CCH-. ), scyle ;
Iu· 4, n z
O
c est i ' hycrccèr.e, le fluci, le chlcre, le trcr.e, l'ioce, ou un çrcupe alkyle, aikcxy, alkylsuifinyle, ai- / kylsuifcnyie, C.*·-, LL,,, CL, Nh0, LHCCr.“ eu F- est si/ 35 céfini ccrr.re ci-cessus eu CGNH, ; /j// I ' f 2 C est l'hydrogène ou un halogène ou un groupe al-kyle ou dialkylami.no D est le fluor, le chlore, le brome, l'iode ; ou un groupe CF^, alkylthio, alkylsulfinyle, alkylsulfonyle, 5 halogenoalkyle, sulfamoyle, formyle, alkylcarbonyle, CN ou diméthylamino ; E est l'hydrogène ou un groupe halogenoalkyle, al- koxy, alkylsulfinyle, alkylsulfonyle, CN, CF,, NH0,
Il -5 ^ C0NH2, NH-CO-R , R ayant la signification déjà in- 10 diquée ;
F a l'une des significations données pour B
R est un groupe -C0N(R^)S09R3 dans lequel , 4 x * R est l'hydrogene ou un groupe alkyle de 1 à 4 I atomes de carbone E 3 15 R est un groupe phényle, pyridyle ou thiényle éventuellement substitué par un ou plusieurs atomes d'halogène, ou groupes alkyle, ou groupes nitro ; ou un radical alkényle ou alkynyle ayant 2 à 4 atomes de carbone ou un radical alkyle de 1 à 4 atomes de carbone éventuellement * > 20 substitue par un ou plusieurs atomes de fluor, chlore, brome ou iode, de préférence CF^, ou par un ou plusieurs des substituants suivants : carboxyle, alkoxycarbonyle de 2 à 5 atomes de carbone, alkylcarbonyle de 2 à 5 atomes de „ carbone, mono ou dialkylcarbamoyle dans lequel les groupes 25 alkyle ont de 1 à 4 atomes de carbone, alkylthio, alkylsulfinyle, alkylsulfonyle, chacun ayant de 1 à 4 atomes de carbone, alkylcarbonyloxyle de 2 à 5 atomes de carbone, al-kylcarbonylamino de 2 à 5 atomes de carbone, ou cyano.
Selon les procéoés connus, les produits de formule 30 (I) peuvent être préparés par réaction entre 25 et 140°C
d'un halogènure d'scioe intermédiaire de formule : c_ys> _^COX / d-: fVow fr~A (II) Π/ 35 yJ -V (f E F / » 3 dans laquelle X est le chlore, le brome ou l'iode, et A, B, C, D, E, F ont les significations déjà indiquées, avec un sulfonamide de formule : 5 R3Sû2NH2 (III) où R3 a la signification déjà indiquée, en présence d'un accepteur d'acide, notamment une amine tertiaire telle que la Ni,h-diméthylaniline ou la pyridine, ou un carbonate de métal alcalin tel que le carbonate de potassium anhydre, ou 10 un fluorure de métal alcalin tel que le fluorure de césium.
Les composés de formule (I) dans laquelle R^ est l'atome d'hydrogène peuvent être alkylés de manière connue, par exemple par réaction d'un diazoalcane de 1 à 4 atomes de carbone, de manière à fournir les produits correspon-15 dants dans lesquels est un groupe alkyle de 1 à 4 atomes de carbone.
Ce procédé de condensation des produits de formule (II) et (III) a de nombreux inconvénients : les rendements sont médiocres (par exemple on peut calculer un rendement A 20 de 27% pour l'exemple 14 de la demande de brevet européen 23392 et 9,5 % pour l'exemple 34). On pense aue c'est la présence d'accepteur d'acide qui abaisse le rendement par le fait qu'il favorise la réaction de diacylation. De plus l'utilisation d'un accepteur d'acide rend l'isolement et la 25 purification des produits finaux plus difficile et plus coûteuse.
Un but de l'invention est de remédier à ces incon-! ’ vénients.
i Le procédé selon l'invention comprend la réaction 30 d'un halogènure d'acide (de préférence un chlorure, un bromure ou un iodure) avec un sulfonamide de formule (III) en l'absence d'accepteur d'acioe et à une température à laquelle l'acide halohycriaue (HCl, HBr, ΗΊ) est éliminé sous forme gazeuse du milieu réactionnel au fur et à mesure de 35 sa fcrmaticn mais sans décomposition appréciable ou proouit / de réaction de formule (I). / i/ h
Grâce eu prccécé selon l'invention, oes rendements notablement plus élevés en cérivés sulfonamides c'acides phénoxybenzoiQues peuvent être ootenus, par exemple des rencE-ments c'au moins environ 3UL et fréouemment c'su moins 5 environ 50¾ et avec un mode ce récupération et de purification ou produit final beaucoup plus simple eue ceux des procéüés connus.
Comme halogénure d'acice mis en oeuvre dans l'invention, on utilise en pratioue un halogénure d'acide de lu formule (II) ; ce préférence en utilise un halogénure dans la formule duquel A est le groupe N02 ou un atome de fluor, de chlore, oe brome ou d'iode ; B est un atome d'ha-loçène ; C, E et F sont l'atome d'hydrogène ; D est le groupe CF_.. On préfère également mettre en oeuvre des I -5 3 15 sulfonamioes oe formule (III) dans laauelle R est un groupe alkyle, spécialement CH^, ou un groupe CF_. f . La température à laquelle le procédé oe l'invention peut être mis en oeuvre cépeno notamment de ce que l'halo-génure d'acide de formule (II) ou le sulfonamide de formule 20 (III) sont l'un ou l'autre en large excès ou de ce aue l'on, utilise, ou non, un solvant ayant des propriétés catalytiques.
Ainsi iGrsoue l'halocénure d'acice (II) est en large excès, c'est à dire que le rapport mdaire (11)/(111) 25 est compris entre environ 1,5 et 5, l'halGgénure d'acide (II) peut servir ce solvant pour la réaction et la température oe réaction peut être comprise entre 6G et 200°C, mais elle est alors oe préférence comprise entre 90 et 16GCC.
3u L'halocénure d'acice (II) n'ayant cas réagi peut être récupéré du milieu réactionnel par lavage avec un solvant inerte tel qu'un hydrocarbure, notamment le pentane, l'hexane, l'heptane, le cyclcpentane, le cyclohexane, le cycloneotane, le benzène, le toluène, le xylèr.e, un hydre-35 carbure halogène notamment les chlcrobenzènes, CS^, le _ / tetrahyGrofurar.ne, le dicxsnne et c'autres. /// f- 5
Guano on utilise un excès ce sulfonamice, c’est à aire auanc le rapport mclaire ces composés (111)/(11) est compris entre 1,5 et 5, la température réactionelle est alors généralement comprise entre 9ü et 2Q0°C et de préfé-5 rence comprise entre 140 et 160°C. En tout état de cause elle coit être au moins suffisante pour faire fondre le milieu réactionnel. L'excès ce Sulfonamide (III) peut être récupéré gu milieu réactionnel par lavage à l'eau ou un autre solvant inerte ce ce réactif (III). lu Les réactifs peuvent aussi être clssous dans un solvant inerte ayant un point c'ébullition supérieur à la température ce réaction par exemple un hydrocarbure liquide, chloré ou non tel que le benzène, le toluène, les xylènes, les mélanges oe xylènes, le cumène, auquel cas la 15 température maximale de réaction est avantageusement légèrement inférieure au point c'ébullition du solvant. Ainsi aans le cas ou cumène qui bout à environ 153°C, la réaction est mise en oeuvre ce préférence entre 13ü et 150°C. L'usage d'un solvant inerte a l'avantage pratique de permettre 20 un meilleur transfert de chaleur dans un procédé à l'échel-*, le industrielle ; il permet aussi d'éviter les surchauffes locales eu milieu réactionnel.
Selon une autre variante de l'invention, on utilise , un solvant ayant une action catalytique à l'égard de la 25 réaction entre l'halogénure d'ecice (II) et le sulfonamide (III) pour fournir le phéncxybenzcylsulfonsmice (I). Le diméthylfcrmamice (=UMF ; cui bout à environ 154°C) et le diméthyiacétamioe (= DMAC ; qui oout à environ 164°C) sont particulièrement avantageux c cet écarc et leur usage per-3u met la mise en oeuvre oe température relativement basses par exemple comprises entre 6U et 12ü°C, ce préférence entre 50 et 11G°C eu encore des températures plus élevées, légèrement inférieures aux points c'ébullition de ces solvants ; la vitesse et réaction est alors plus rspice.
35 Les exemples suivants oennes a titre non limitatif , illustrent l'invention et rentrent comment elle neut être / i !' =: 6 1 mise en oeuvre.
Î Exemple I
Gr mélange 2 c (u, C21 rr-clt) ce méthane sulfonsmice avec 3,6 c (u,ul mole) ce chlorure ce l'acide 5- 2'-chlc- ! 5 rc-t ' - (tri f lucrométhyl ) rhéncxy -2-nitrcbenzc-ïcue. On chauffe le mélange 2U minutes à 15G°C. L'acice chlorhy- cricue se cépage eu milieu réactionnel au fur et à mesure de sa formation, ün refroidit ; en a une huile noire αυ'οπ dissout cans ce la scuce soueuse ; on filtre, acidifie le l IG filtrat à l'aide d'hCl dilué, ce qui précipite le produit :j oe formule (IV). Cn a ainsi obtenu, avec un rendement ce 71 i /6, 3,1 g oe procuit fonçant à 195-197°C et ayant une bande -1 i: ‘ d’absorption infrarouge à 1652 cm (croupe C=Q).
• Ce preauit a pour formule : :j 15
Cl CO-NH-SO^-CH., _ · _/ 2 3 GF γ —O— r NO„ (IV) ! \_, _ 2 t:- : 2 u p Exemple 2 f On reprocuit l'exemple I mais en utilisant 250 g oe i| chlorure c'scioe et 13G ç de méthane sulfonamide. Le pro- ! ^ cuit ce réaction est isolé directement après refroidisse- | 25 ment gu mélange par recristillisation Gans 1'iscpropancl.
ün a un rendement ce u 2 (165 c) en produit ce formule (IV). La structure ce ce produit est confirmée par infrarouge (bande o'abserptior à 1692 ern'^) et par résonance magnétïcue nucléaire (sirculet à 3,5 ppr? ; multiplet à c,C7 3G ppm).
I En appiigu&nt re procédé ce l'exemple oe la cernanee
Si ce brevet européen 23352 en utilisant la pyricine comme accepteur d'acice, r£ renrenent n'a été eue ce 25 2 / i S/

Claims (5)

  1. 7
  2. 5 REVChuICATIGhS i) - Procécé ce préparation ce dérivés phénoxybenzoïques à groupe sulfcnamice ce formule lü C ,B H \ / y D—/TV 0 \Λ il) / N E F 15 et ses sels, cans laquelle A est l'hyoroçène, le fluor, le chlore, le brome, l'iode, un groupe nitro; -N=NCF^ ; Pü^l-L et ses esters d'al-2G kyle de 1 à 4 atomes de carbone ; NH2, NHGH, N* ; un croupe carbGxyie ou l'un de ses cérivés fonctionnels ; un groupe mono ou dialkylamino ; un groupe NH-CO-R^ cans lequel R^ est un racical alkyle ou alkoxyle ou mcncalkyla- minc ou aialkylaminc ; un groupe alkyle ; trialkylammonio, * 2
  3. 25 UHSG^R où R^ est ur. racical alkyle ou phényie ; NHüubHSG^r , cl a la signification Géjs inciouée/ alkylthic, aluyisulfinyle, aikyisuifonyle, oislkylsui- fonio, cyanosclfonyle, hycroxy, alkancyicxy, alkoxy, alkoxy suostiiué par _r. aikoyycartcr.\ le, $h, nitrcsc, -SCb·, azioe, 3>u —l\=K-P-(lwη-· ;^ , scyie ; O E est 1'hycroçènt, le fluor, le chlore, le brome, l'îcoe, ou ur croupe alkyle, sikcxy, slkyisulfinyle, ai- / kylsuïf cnyle, ,, î'.Üv, CI», Ni-,.., NhÜCn“ eu r.~ est y~,/ 55 céfini comme ci-cessus ou CONR^ ; /1/ l // / 1 >- C est i'hycrcgène eu un halogène ou un groupe al-kyle ou Gialkylaminc L· est le fluor, le chlore, le crcme, l'iooe ; ou un groupe CF,, aikyithic, slkylsulfinyle, alkylsulfonyle, Î3 rsiccencalkyie, sulfamcyie, fcrrr.yie, slkylcsrbonyle, CK ou ciméthylsmino ; E est l'nycrcçène eu un croupe halccéncai.kyie, sl- koxy, alkylsulfinyle, slkylsulfonyle, CN, CF,, Nh0, 11 % 1 CüNH^, NH-LC-k , R ayant la siçnificeticn oéjà inoi- lu quée ; F a l'une ces significations connées pour B R est un groupe -COk(RA JSCvR"5 oans lequel k est I'hycrcgène ou un croupe alkyie oe 1 à A | atorr.es oe c a roc ne j 13 h' est un groupe pr.ényie, pyridyle eu thiényle ! éventuellement substitué par un ou plusieurs atomes ti'halo- [: gène, ou groupes aiKyle, ou groupes nitre ; ou un racical I alkényle ou alkynyie ayant 1 a u atomes oe carbone ou un racical alkyie ce 1 à A atomes ce carbone éventuellement ! 2U substitué par un ou plusieurs atomes ce fluor, chlore, i brome uu ioce, ce préférence CF,, eu par un ou plusieurs j ces substituants suivants : carboxyle, alkcxycarbonyle oe 2 | à 3 atomes ce carrent, alkyicarbonyle ce 2 s 5 atomes ce j carbcne, m.onc eu cialkylcarbamoyle dans lecuel les groupes i 21 alkyie cm ce 1 à u atomes ce carbone, aikyithic, alkyisul- ! finyie, alkylsulfonyle, chacun ayant ce 1 à A atomes ce j caroone, alkylcaiccryicx\le ce 2 à 3 atomes ce carbone, | _ aikylcarbonylsmino ce 2 à 3 atomes ce carbcne, ou cyano, le : cit prccécé consistant à faire réagir un baJcgérure c'acice i 3u oe formule / I C B COM / i \ / (_/ A4 ; & / t )-û~ f—h di) (j? i 1'/ v F / j " **' j i c. ** cens iacuelle X est un atcrne ce chlore, ce brome eu c’ioce et a, Γ-, u, \j, E, F ent les significations inciouées cens la formule (1), avec un sulfcnam.ice Ge fcrrr.ule h3 SG0 {-.h (iii), r/ ayant également 1b signif icaticr-3 céjà incicuée, le Gît prccécé étant caractérise en ce que la réaction est effectuée en i'acsence c'accepteur a'acide et s une température à laquelle i'hycrscioe gazeux sous-procuit est éliminé eu milieu réactionnel au fur et à mesure ce sa formatier,, cette température étant inférieure à lu la température ce cécompositicn eu procuit ce formule (I). 2) - Procéoe selon la revencication 1 caractérisé en ce qu'en opère en présence c'un excès c'halcçénure c'acioe de formule (II). 3) - Prccécé seien le revendication 2 caractérisé en ce eue 15 le rapport molaire halcçénure c'scice Ge formule (II)/sul- fonamice ce fermuie (III) est compris entre 1,5 et 5 4) - Procédé selon l'une ces revencications 2 ou 3 caractérisé en ce eue la température réactionnelle est comprise entre 6ü et 2ûû°C, ce préférence entre Su et 16Q°C ja. 2ü 5) - Procécé' selon la revencication 1 caractérisé en ce - , au'on opère en présence c'un excès ce sulfonamioe. e) - Procécé selon la revencication 5 caractérisé en ce eue le rapport molaire sulfonamioe oe formule (III)/haicgènure , c'acioe ce formule (II) est compris entre 1,5 et 5 ^3 7) - Procécé selon l'une ces revencications 5 ou C caracté rise en ce eue la température réactionnelle est comprise entre Sü et 2U0°C, ce préférence entre iau et i£ü°C. b) - Prccécé seien ;'une ces revencicaticns 1 à 7 caractérisé en ce cLt i'cr cqère en présence c'ur solvant ayant cr ^ peint c'ébuliitiPT. supérieur à la température réactionnelle. 5) - Procécé selon la revencicaticn 6 caractérisé en ce eue le solvant est un n\ crccarcure. iu) - Prccécé sels” i£ revencication 9 caractérisé en ce que _e st-’.arc est *e cl·”tre et eue la température est cc~- J 35 prise entre et i5oDt. /y if i i i i i s i u £ 1-0 - Prccécé selon l'une ces revencicetions 1 a 8 caracté- E risé en ce eu'on opère en présence c'ur, solvant ayant aes propriétés cstalyticues ε l'éparc ce le réecticn. 12) - Prccécé selon la revencicaticn II caractérisé en ce 3 eue le solvant est le cin.éthylforrr.amice ou le diméthylacé- tamice et eue la température est comprise entre êü°C et la température c ' étulliticn eu servant. 13) - nrccécé selon la revencication 12 caractérisé en ce que la température est supérieure a fu0L. I iu 14) - Procécé selon l'une ces revencications 1 è 13 carac- I térisé en ce eue, caris les fcrrrules (I) et (II), B et X Isont l'atome ce chlore, A est l'atcme Ge chlore ou NO„. 2’
  4. 5 L, ii, F sont l'atcme c'hycroçène, L est CF^. S 15) - Prccécé selon i'ure ces revencications 6 eu 7 carac- 15 térisé en ce eue le suifcnar.ice est tel eue h-5 est un 1 croupe slkyie ou UF_, ce préférence méthyle. Ί W O '! 16) - Procécé selon I'ure ces levencicaticns 1 à 15 carac- iij térisé en ce eue l'on effectue la réaction entre $
  5. 1 Cl CO-C1 1 ._/ _/ Icf3 —y r o— t y N02 Dessins :.............pianenes pages dont .....Ol....... page de garde __________é.......pages de description * __________H....... pages de revendications % ________abrégé descriptif J Luxembourg, le Z6 jy|i4982 J Lem^^ataire : i' Charles München i f i* [. i
LU84295A 1981-07-27 1982-07-26 Procede de preparation d'acides phenoxybenzoiques LU84295A1 (fr)

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US28693881A 1981-07-27 1981-07-27
US28693881 1981-07-27

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LU84295A1 true LU84295A1 (fr) 1984-03-22

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JP (1) JPS5826860A (fr)
KR (1) KR880002591B1 (fr)
AT (1) AT385985B (fr)
BE (1) BE893940A (fr)
BR (1) BR8204357A (fr)
CA (1) CA1194472A (fr)
CH (1) CH652384A5 (fr)
DD (1) DD203716A5 (fr)
DE (1) DE3227847A1 (fr)
DK (1) DK333282A (fr)
ES (1) ES8306108A1 (fr)
FR (1) FR2510105A1 (fr)
GB (1) GB2103611B (fr)
HU (1) HU191186B (fr)
IE (1) IE53978B1 (fr)
IL (1) IL66197A (fr)
IT (1) IT1198399B (fr)
LU (1) LU84295A1 (fr)
NL (1) NL8202994A (fr)
PL (1) PL136683B1 (fr)
PT (1) PT75322B (fr)
RO (1) RO85388B (fr)
SU (1) SU1215620A3 (fr)

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GB8628109D0 (en) * 1986-11-25 1986-12-31 Ici Plc Chemical process
US11834714B2 (en) 2021-12-20 2023-12-05 Enumerix, Inc. Detection and digital quantitation of multiple targets

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DE2960664D1 (en) * 1978-01-19 1981-11-19 Ici Plc Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them
DE3068101D1 (en) * 1979-07-18 1984-07-12 Ici Plc Diphenyl ether compounds, and herbicidal compositions and processes utilising them

Also Published As

Publication number Publication date
RO85388B (ro) 1984-11-30
IL66197A0 (en) 1982-11-30
FR2510105A1 (fr) 1983-01-28
DD203716A5 (de) 1983-11-02
KR880002591B1 (ko) 1988-12-03
GB2103611B (en) 1985-04-03
CH652384A5 (fr) 1985-11-15
PL136683B1 (en) 1986-03-31
IL66197A (en) 1985-11-29
IE53978B1 (en) 1989-05-10
DK333282A (da) 1983-01-28
HU191186B (en) 1987-01-28
DE3227847A1 (de) 1983-02-10
ATA290082A (de) 1987-11-15
GB2103611A (en) 1983-02-23
IT8222545A0 (it) 1982-07-23
BR8204357A (pt) 1983-07-19
IT8222545A1 (it) 1984-01-23
BE893940A (fr) 1983-01-26
JPH0149262B2 (fr) 1989-10-24
PT75322B (fr) 1985-11-29
JPS5826860A (ja) 1983-02-17
ES514352A0 (es) 1983-05-01
SU1215620A3 (ru) 1986-02-28
FR2510105B1 (fr) 1984-09-07
KR840000466A (ko) 1984-02-22
AT385985B (de) 1988-06-10
PL237639A1 (en) 1983-05-23
CA1194472A (fr) 1985-10-01
PT75322A (fr) 1982-08-01
IE821786L (en) 1983-01-27
IT1198399B (it) 1988-12-21
ES8306108A1 (es) 1983-05-01
NL8202994A (nl) 1983-02-16
RO85388A (fr) 1984-11-25

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