HU191186B - Process for producing sulfonamide derivatives of phenoxy-benzoic acid - Google Patents

Process for producing sulfonamide derivatives of phenoxy-benzoic acid Download PDF

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Publication number
HU191186B
HU191186B HU822401A HU240182A HU191186B HU 191186 B HU191186 B HU 191186B HU 822401 A HU822401 A HU 822401A HU 240182 A HU240182 A HU 240182A HU 191186 B HU191186 B HU 191186B
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formula
alkyl
trifluoromethyl
hydrogen
reaction
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HU822401A
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German (de)
English (en)
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El-Ahmadi I Heiba
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Rhone-Poulenc Agrochimie,Fr
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Publication of HU191186B publication Critical patent/HU191186B/hu

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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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    • 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
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    • 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
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    • 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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    • 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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    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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Description

A találmány tárgya javított eljárás gyomirtó készítmények hatóanyagaiként alkalmazható fenoxi-benzoesav-szulfonamid-szárma7.ékok előállítására.
Egyes, szulfonamidocsoportol tatalmazó fenoxibenzoesav-származékok gyomirtó tulajdonságai a 3416. és a 23 392. számú európai szabadalmi leírásokból ismertek.
Az említett szabadalmi leírások a (I) általános képletű vegyületeket és sóikat ismertetik. A képletben: A jelentése hidrogén-, fluor-, klór-, bróm- vagy jódatom, nitrocsoport, trifluor-metil-diazo-csoport (—N = NCF3), aminocsoport, hidroxi-aminocsoport, diazóniumcsoport, olyan
-NH-CO-R1 általános képletű csoport, amelyben R* 1 - 4 szénatomos alkil-, 1 -4 szénatomos alkoxi- vagy di(l — 4 szénatomos alkil)ainino-csoporlot jelen!;
—4 szénatomos alkilcsoport, — NHSO2 — (1 —4 szénatomos alkilj-csoport, tiocianátocsoport, azidocsoport, trifluor-metil-csoport vagy - N = N - P - (OCH3)2 csoport;
I o
B jelentése hidrogén-, fluor-, klór-, bróm- vagy jódatom, 1 —4 szénatomos alkil-, I -4 szénatomos alkil-szulfinil-, trifluor-metil-, nitro- vagy cianocsoport ;
C jelentése hidrogén- vagy halogénatom vagy 1 - 4 szénatomos alkilcsoport;
L jelentése fluor-, klór-, bróm- vagy jódatom, trifluor-metil- vagy nitrocsoport;
E jelentése hidrogénatom, halogénatom vagy trifluor-metil-csoport ;
M jelentése hidrogén- vagy halogénatom vagy trifluor-metil-csoport ;
R4 hidrogénatomot vagy 1 -4 szénatomos alkilcsoportot jelent;
R3 jelentése — halogcnaloinmal, I—4 szénatomos alkilcsoporttal vagy. nitrocsoporttal adott esetben szubsztituált - fenilcsoport; vagy olyan 1 — 4 szénatomos alkilcsoport, amely fluor-, klór-, bróm- vagy jódatommal adott esetben szubsztituált (előnyösen trifluor-metil-csoport) vagy benzil-, indanil- vagy (1-4 szénatomos alkoxi)karbonil-(l -4 szénatomos alkilj-csoport.
Az ismert eljárásnak megfelelően a (I) általános képletű vegyületek (II) általános képletű savhalogenid
- X klór-, bróm- vagy jódatom, A, B, C, L, E és M a fenti jelentésű - és (III) általános képletű szulfonamid reagáltatásával állíthatók elő — R3 a fenti jelentésű — 25—140 °C-on savmegkötő szér — elsősorban tercier amin, így Ν,Ν-dimetil-anilin vagy piridin; vagy alkálifém-karbonát, így vízmentes káliumkarbonát; vagy alkálifém-fluorid, így cézium-fluorid
- jelenlétében.
A (I) általános képletű vegyületek — R4 hidrogénatom - ismert módon alkilezhetők, például 1-4 szénatomos diazoalkánnal; így olyan vegyületeket kapunk,· amelyek képletében R4 1 - 4 szénatomos alkilcsoport.
Á (II) általános képletű vegyületek és a (III) általános képletű vegyületek kondenzálásának számos hátránya van. Az elérhető kitermelés mérsékelt (például a 23 392. számú európai szabadalmi leírás 14. példájában 27 %, és a 34. példában 9,5 %). Feltételezhető, hogy a savmegkötő szer jelenléte rontja a kitermelést, mivel a diacilezési reakciónak kedvez. A savmegkötő szer a végtermék elkülönítését és tisztítását is megnehezíti és drágítja.
A találmánnyal célkitűzésünk a fenti hátrányok kiküszöbölése.
A találmány szerinti eljárás során egy savhalogenidet, előnyösen -kloridot, -bromidot vagy -jodidot reagáltatunk (III) általános képletű szulfonamiddal savmegkötő szer nélkül olyan hőmérsékleten, amelyen a hidrogén-halogenid (hidrogén-klorid, -bromid vagy -jodid) a (1) általános képletű reakciótermék érzékelhető bomlása nélkül olyan ütemben távozik a reakcióközegből gázként, amilyen ütemben képződik.
A találmány szerinti eljárással lényegesen nagyobb kitermeléssel állíthatók elő a fenoxi-benzoesavak szulfönamid-szánnitzékíii - legalább 30 %-os, gyakran 50 % kitermeléssel - valamint a végtermék elkülönítése és tisztítása is lényegesen egyszerűbbé válik, mint az ismert eljárásnál.
A találmány szerint savhalogenidként (II) általános képletű savhálogenidet használunk. Előnyösen olyan halogenidből indulunk ki, amelynek (II) általános képletében A nitrocsoport vagy fluor-, klór-, brómvagy jódatom, B halogénatom, C, E és M hidrogénatom és L trifluor-metil-csoport. Előnyösen olyan (III) általános képletű szuífonamidot használunk, amelyben R3 alkilcsoport, előnyösen metilcsoport, vagy trifluor-metil-csoport.
A találmány szerinti eljárás műveleti hőmérséklete elsősorban attól függ, hogy a (II) általános képletű savhalogenidet vagy a (III) általános képletű szulfonamidot nagy fölöslegben használjuk-e vagy adott esetben katalitikus hatású oldószert alkalmazunk-e.
Ha a (II) általános képletű savhalogenidet nagy fölöslegben alkalmazzuk, azaz a (II) és a (IÍI) általános képletű vegyületek mólaránya legalább 1,5-5, a (II) általános képletű savhalogenid oldószerként szolgálhat és a reakcióhőmérséklet 80 °C — 200 ’C lehet; előnyösen 90-160 ’C-on dolgozunk.
A reagálatlan (II) általános képletű savhalogenidet közömbös oldószerrel való mosással visszanyerhetjük, például szénhidrogénnel - így pentánnal, hexánnal, hcptánnal, ciklopentánnal, ciklohexánnal, cikloheptánnal, benzollal, toluollal, xilollal — vagy halogénezett szénhidrogénnel — elsősorban klór-benzollal -, továbbá szén-diszulfiddal, tetrahidrofuránnal, dioxánnal mosva.
Ha a szulfonamid fölöslegével dolgozunk, azaz a (III) és a (II) általános képletű vegyűlet mólaránya
1,5 - 5, a reakció hőmérséklete általában 90 és 200 ’C között lehet, előnyösen 140-160 °C. A hőmérsékletnek minden esetre elegendő nagynak kell lenni, hogy a eakcióközeg olvadék legyen. A (III) általános képle*ű szulfonamid fölöslege a reakcióelegyből vízzel való mosással vagy a (III) általános képletű reagenssel szemben közömbös oldószerrel való mosással visszanyerhető.
A reakciópartnerek olyan közömbös oldószerben is oldhatók, amelynek forráspontja a reakcióhőmérsékiet fölött van, például folyékony, adott esetben klórozott szénhidrogénben, így benzolban, toluolban, xilolban, xilol elegyben, kumolban, és a maximális reakcióhömérséklct előnyösen valamivel az oldószer forráspontja alatt van. Például kurnol használata esetén -23
191 186 amely körülbelül 153 °C-on forr — előnyösen 130- 150 ’C-on dolgozunk.
A találmány szerinti eljárás egy másik változata szerint olyan oldószert alkalmazunk, amely a (U) általános képletű savhalogenid és a (III) általános képletű szulfonamid (I) általános képletű fenoxibenzoil-szulfonamidot eredményező reakciójára katalitikus hatást fejt ki. Ilyen tekintetben különösen előnyös a dimetil-formamid (154 ’C-on forr) és a dimetil-acetamid (164 ’C-on forr). Ezek az oldószerek lehetővé teszik a munkát viszonylag alacsony hőmérsékleten, például 80—120 ’C-on, előnyösen 90—110 ’C-on, de kissé magasabb, valamivel az említett oldószerek forráspontja alatti hőmérsékleten is, amelyen a reakciósebesség nagyobb.
A következő példák a találmány részletesebb magyarázatául szolgálnak.
I. példa 20 g (0,021 mól) metánszulfonamidot összekeverünk, 3,8 g (0,01 mól) 5-[2’-klór-4’-(trifluor-metil)fenoxiJ-2-nitro-benzoesavkloriddal. Az elegyet 20 percig 150 ’C-on melegítjük; a reakcióclcgyből a képző- 2r dött hidrogén-klorid eltávozik. Az elegyet ezután lehűtjük. Fekete olajat kapunk, amelyet vizes nátriumhidroxid oldatban feloldunk. Szűrés után a szüredéket híg sósavval megsavanyitva a (IV) képletű vegyület kiválik. A kitermelés 3,1 g (71 %). Olvadáspontja 195- 197 ’C; infravörös abszorpciós sávja 1692 cm1 (C = 0).
2. példa
Az 1. példában leírt módon járunk el, de 250 g savkloridot és 130 g mctánszulfonnmidol használunk. A reakcióterméket közvetlenül lehűlés után az elegyből izopropanolból átkristályosítva különítjük el. A kitermelés 185 g (64 %) (IV) általános képletű vegyület. A vegyület szerkezetét infravörös színképével (abszorpciós sáv 1692 cm*-nél) és NMR spektrumával (szingulett 3,5 ppm, multiplelt 8,07 ppm) igazoltuk.
Összehasonlításul a 23 392. számú európai szabadalmi leírás szerinti eljárással dolgoztunk, savmegkötőszerként piridint használva; így a kitermelés csak 25 % volt.
Az 1. és 2. példákban leírtakkal analóg módon eljárva állítjuk elő a következő táblázatokban felsorolt (I) általános képletű vegyületeket.
I. táblázó ’ (C és E hidrogénatom)
R3 A B M L R4 Olvadáspont, ’C
ch3 no2 Cl H cs H 201
c2h5 no2 Cl H cs H 161,5
c3h7 no2 Cl H CS H 179
c4h9 no2 Cl H cs H 183
c6h13 no2 Cl H cs H 171
ch3 no2 Cl H cs ch3 117
ch3 Cl Cl H CS H 185,5
ch3 Cl Cl H CS ch3 116
ch3 Br Cl H H 164
ch3 Br Cl H cs ch3 108
ch3 H Cl H CS H 168
c4h9 H Cl H cs H 102
ch2c6h5 H Cl H cs H 186,5
ch3 H H H CS H 124,5-126
ch3 H CN . H Cs H 198-199
ch3 no2 CN H cs H 171-172
ch3 no2 Cl H Cl H 182-183
c4h9 no2 Cl H Cl H 198-200
ch3 H Cl H Cl H 184-187
ch3 Br Cl H Cl H 146-147
ch3 no2 Cl Cl Cl H 227,5-228
ch3 no2 Br Br Br H 237-239
ch3 no2 ch3 H Cl H 177,5- 178,5
ízoC3H7 no2 Cl H CF, H 146
ch3 H cf3 H Cl H 129- 130
ch3 no2 Cl H cs H 100
c3h7 Cl Cl H cf3 H 146
c4h, Cl Cl H CS H 149,5
‘ 3
191 186
11. táblázat (Λ4 hidrogénatom)
A B c L E M R3 Olvadáspont, ’C
no2 Cl H cf3 H H c6h5 123-125
no2 Cl H cf3 H H 5-indanil 110-112
no2 Cl H cf, H H . C6H3.2-NO2-4Cl 154-156
no2 Cl H cf3 H H . C6H,. 2 — 0,5—NO2 180-183
no2 Cl H cf. H H . C6H4 . p . ch3 105-108
no2 Cl H cf3 H H ~(CH2)3CI 116-119
no2 Cl H cf, H H -ch,co2ch, 158-160
no2 Cl H cf3 H H -ch2ci 145-148
no2 Cl H cf3 H H .C6H4.p-I 167
no2 Cl H Cl H H • (CH2)3C1 176-178
H Cl H F2 H H - (CH2)3C1 118-120
NHCOCH, Cl H cf3 H H ch. 201
NHCOCE, Cl II CT, 11 II cn, 207
NHSO2CH, Cl H cf3 H H ch3 169
nhco2c2h5 Cl H cf, H H ch3 204
NHCON(CH3)2 Cl H cf3 H H ch, 156
n = n-cf3 Cl H cf3 H H CH, 151
NHOH Cl H cf3 H H CH, 143
N2 + Cl H cf3 H H ch, 160
ch3 Cl H cf3 H H ch3 142
no2 no2 H cf3 H H ch3 184-188
no2 Cl H Cl Cl H ch3 170-171
no2 no2 H cf3 H Cl ch3 206
nh2 Cl H cf, H H ch, 184-185
no2 no2 H cf3 H H CH, . 123 (bomlik)
-SCN Cl H cf, H H ch3 135 (bomlik)
-N3 Cl H cf3 H H ch3 119 (bomlik)
no2 SOCHj H CHj H H CH, 158-160
-N = N-P(OCH,)2 Cl H CF3 H H ch3 159 (bomlik)
no2 F F cf3 F F CH, 177-177,5 .
H Cl H H cf, H CH, 132-133
no2 . Cl H H cf3 H CH, 204-205
H Cl H no2 H H CH, 212-214
no2 H Cl H Cl H CH, 156
H no2 H cf3 H H CH, 155-157
no2 no2 H Cl H H CH, 117-121
cf, Cl H cf3 H H CH, 188
no2 H ch3 Cl H H CH, 171-173
Szabadalmi igénypontok

Claims (14)

1. Eljárás (I) általános képletű fenoxi-benzoesavszulfonamidok és sóik előállítására — a képletben :
A jelentése hidrogén-, fluor-, klór-, bróm- vagy jódatom, nitrocsoport, trifluor-metil-diazo-csoport, aminocsoport, hidroxi-amino-csoport, diazóni- g0 umcsoport, olyan — NH-CO-R' általános képletű csoport, amelyben R1 1—4 szénatomqs alkil-, 1-4 szénatomos alkoxi- vagy di(l — 4 . szénatomos alkil)-amino-csoportot jelent; 1-4 szénatomos alkilcsoport, — NHSO2-(1 — 4 szén- 65 atomos alkil)-csoport, tiocianátocsoport, azidocsoport, trifluor-metil-csoport vagy - N = N- P - (OCH,)2 csoport;
i
O
B jelentése hidrogén-, fluor-, klór-, bróm- vagy jódalom, 1 -4 szénatomos alkil-, 1-4 szénatomos alkil-szulfinil-, trifluor-metil-, nitro- vagy cianocsoport,
C jelentése hidrogén- vagy halogénatom vagy I -4 szénatomos alkilcsoport;
191 186
L jelentése fluor-, klór-, bróm- vagy jódatom, trifluor-metil- vagy nitrocsoport:
E jelentése hidrogénatom vagy halogénalom vagy trifluor-metil-csoport;
M jelentése hidrogén- vagy halogénatom vagy trifluor-metil-csoport;
R4 hidrogénatomot vagy 1 - 4 szénatomos alkilcsoportot jelent;
R3 jelentése halogénatommal, 1 -4 szénatomos alkilcsoporttal vagy nitrocsoporttal adott esetben szubsztituált fenilcsoport; vagy olyan 1—4 szénatomos alkilcsoport, amely fluor-, klór-, brómvagy jódatommal adott esetben szubsztituált; vagy benzil-, indanil- vagy (1—4 szénatomos alkoxi)-karbonil-(I — 4 szénatomos alkil)-csoport (II) általános képletű savhalogcnid — a képletben X klór-, bróm- vagy jódatomot jelent, A, B, C, L, E és M az előzőkben megadott - és (III) általános képletű szulfonamid — a képletben R4 és R3 az előzőkben megadott — reagáltatásával azzal jellemezve, hogy a reagáltatás t snvmcgkötőszer alkalmazása nélkül adott esetben oldószer jelenlétében
a) a (II) általános képletű savhalogenid feleslegével
80-200 °C-on; vagy
b) a (III) általános képletű szulfonamid feleslegével
90-200 ’C-on végezzük és a képződő gázállapotú hidrogén-halogenidet eltávolítjuk.
2. Az 1. igénypont szerinti a) eljárás azzal jellemezve, hogy a (II) általános képletű savhalogenidet és a (III) általános képletű szulfonamidot 1 : (1,5- 5) mólarányban reagáltatjuk.
3. Az 1. vagy 2. igénypont szerinti a) eljárás azzal jellemezve, hogy 90—160 ’C-on reagáltatunk.
4. Az I. igénypont szerinti b) eljárás azzal jellemezve, hogy a (III) általános képletű szulfonapiidot és a (II) általános képletű savhalogenidet I :(1,5-5) mólarányban reagáltatjuk.
5. Az 1. vagy 4. igénypont szerinti b) eljárás azzal jellemezve, hogy 140- 160 ’C-on reagáltatunk.
6. Λζ I - 5. igénypontok bármelyike szerinti eljárás azzal jellemezve, hogy olyan oldószer jelenlétében reagáltatunk, amelynek forráspontja a reakcióhőmérséklet fölött van.
7. A 6. igénypont szerinti eljárás azzal jellemezve, hogy oldószerként szénhidrogént használunk.
8. A 7. igénypont szerinti eljárás azzal jellemezve, hogy oldószerként kumolt használunk és 130-450 ’C-on dolgozunk.
9. Az 1 - 6. igénypontok bármelyike szerinti eljárás azzal jellemezve, hogy a reakciót katalizáló oldószer jelenlétében játszatjuk le.
10. A 9. igénypont szerinti eljárás azzal jellemezve, hogy oldószerként dimctil-formamidot vagy dimetilacctamidot használunk, valamint 80 ’C és az oldószer forráspontja között dolgozunk.
11. A 10. igénypont szerinti eljárás azzal jellemezve, hogy 90 ’C fölött dolgozunk.
12. Λζ 1 — II. igénypontok bármelyike szerinti eljárás olyan (I) általános képletű vegyület előállítására, amelynek képletében B klóratomot, A klóratomot vagy nitrocsoportot, C, E és M hidrogénatomot és L trifluor-metil-csoportot jelent, azzal jellemezve, hogy olyan (II) általános képletű vegyűletet reagáltatunk, amelynek képletében A, B, C, L, E és M a fenti és X klóratom.
13. A 4. vagy 5. igénypont szerinti eljárás azzal jellemezve, hogy olyan (II) általános képletű szulfonamidot reagáltatunk, amelynek képletében R3 alkilcsoportot vagy trifluor-metilcsoportot, előnyösen metilcsoportot jelent.
14. Az I - 13. igénypontok bármelyike szerinti eljárás azzal jellemezve, hogy 5-[2'-klór-4'-(trifluormetil)-fenoxi]-2-nitro-benzoesav-kloridot metán-szulfonamiddal reagáltatjuk.
HU822401A 1981-07-27 1982-07-26 Process for producing sulfonamide derivatives of phenoxy-benzoic acid HU191186B (en)

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IE53978B1 (en) 1989-05-10
IT8222545A1 (it) 1984-01-23
DK333282A (da) 1983-01-28
KR840000466A (ko) 1984-02-22
IL66197A0 (en) 1982-11-30
ES514352A0 (es) 1983-05-01
GB2103611B (en) 1985-04-03
SU1215620A3 (ru) 1986-02-28
KR880002591B1 (ko) 1988-12-03
DD203716A5 (de) 1983-11-02
GB2103611A (en) 1983-02-23
ES8306108A1 (es) 1983-05-01
RO85388B (ro) 1984-11-30
CA1194472A (en) 1985-10-01
PT75322A (fr) 1982-08-01
AT385985B (de) 1988-06-10
IL66197A (en) 1985-11-29
RO85388A (ro) 1984-11-25
IE821786L (en) 1983-01-27
IT8222545A0 (it) 1982-07-23
FR2510105B1 (hu) 1984-09-07
PT75322B (fr) 1985-11-29
NL8202994A (nl) 1983-02-16
CH652384A5 (fr) 1985-11-15
DE3227847A1 (de) 1983-02-10
BR8204357A (pt) 1983-07-19
IT1198399B (it) 1988-12-21
JPS5826860A (ja) 1983-02-17
PL237639A1 (en) 1983-05-23
FR2510105A1 (fr) 1983-01-28
ATA290082A (de) 1987-11-15
BE893940A (fr) 1983-01-26
JPH0149262B2 (hu) 1989-10-24
PL136683B1 (en) 1986-03-31
LU84295A1 (fr) 1984-03-22

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