FR2546165A1 - PROCESS FOR THE PREPARATION OF SULFONAMIDE GROUP PHENOXYBENZOIC ACIDS - Google Patents

Abstract

PROCESS FOR PREPARING PHENOXYBENZOIC ACIDS WITH A SULFONAMIDE GROUP BY REACTION OF HALOGENIDE OF PHENOXYBENZOIC ACID POSSIBLY IMPURE ON A SULFONAMIDE IN THE PRESENCE OF A HALOGENATION AGENT SUCH AS P (O) CL.

Description

The present invention relates to an improved process

  preparation of certain phenoxy acid derivatives

  sulfornanie group benzoids with properties

herb ic i de s.

  Herbicidal derivatives of phenoxybenzoic acids containing a sulfonamide group (or N-sulfoinyl-phenylbenzimides) are known in European patent applications 3416, 233 92

and Japanese N o 8 1 06654.

  These patent applications disclose many products of this type, and especially formula products.

C B CO-N 1 I-502-R 3

D O t A (1)

3.5 E

  and their salts, wherein A is hydrogen, fluorine, chlorine, bromine, iodine, a nitro group; -N = NCF 3; Po 03 12 and its alkyl esters of 1 1 4 carbon atoms; N II 2, NHIOH,

  Or; a carboxyl group or one of its derivatives

  tional; a mono or dialkylarrino group; a Nil-GO-R 1 group in which P is an alkyl or alkoxyl or monoalkylamino or dialkylamino radical; a group

2 2 2

  alkyl or phenyl radical; NHCON Hf 502 R, where R has the meaning already indicated: alkylthio, alkyl sulfinyl, alkylsulfonyl, dialkylsulfonio, cyanosulfonyl, hydroxy,

  alkanoyloxy, alkoxy, alkoxy substituted by uhn alkoxycarbon

  bonyle, SE, nitroso, -SCN, azide, CF 3, 3 Jacl O J B is hydrogen, fluorine, chlorine, brone,

  iodine, or an alkyl, alkoxy, alkylsulfinyl, alkyl-

  sulfonyl, CF 3, NO 2, CN, I 12, NIUCOR or R is defined as above, or CO 1 i I 2; C is hydrogen or a halogen or an alkyl or dialkylamino group D is fluorine, chlorine, bromine, iodine; or CF 3, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, sulfamoyl, fornyl, allylcarbonyl, CN or dimethylamino; E is hydrogen or a haloalkyl, alkoxy, alkylsulphinyl, alkylsulfonyl, CN, CF 3, Ni 12, CONII 2 group,

1 1 3 2

  if-CO-T, R 1 having the meaning already indicated; W is a trivalent nitrogen atom or a group -C (G) = G has one of the meanings given for B

  R 3 is a phenyl, pyridyl or thienyl group

  it is substituted with one or more halogen atoms, or alkyl groups, or nitro groups; or an alkenyl or alkynyl radical having 2 to 4 carbon atoms or an alkyl radical of 1 to 4 carbon atoms optionally substituted by one or more fluorine, chlorine, bromine or iodine atoms, preferably CF 3, or by one or more substituents: carboxyl, alkoxycarbonyl of 2 to 5 carbon atoms, alkylcarbonyl of 2 to 5 carbon atoms, mono or dialkylcarbamoyl in which the groups

  alkyl groups have from 1 to 4 carbon atoms, alkylthio, alkylsulphonyl

  finyl, alkylsulfonyl, each having 1 to 4 carbon atoms, alkylcarbonyloxyl of 2 to 5 carbon atoms,

  alkylcarbonylamino of 2 to 5 carbon atoms, or cyano.

  According to the known processes, the products of formula (I) can be prepared by reaction between 25 and 40 ° C of an intermediate acid halide of formula:

C B OOX

D O A (II)

E

2546,165

  in which X is chlorine, bromine or iodine, and A, B, C, D, E, G have the meanings given in 6, with a sulphonamide of the formula: FI 3 SO 2 K} 1 211 P 3 so 2 ru 2 (III)

3 2 '2

  It has the meaning already indicated, generally in the presence of an acid acceptor, especially a tertiary amine such as N, N'-ethylaniline or pyridine, or an alkali metal carbonate such as sodium carbonate. anhydrous potassium, or an alkaline mental fluoride such as

fluoride of c 6 sium.

  The compounds S of formula (I) can then be alkylated in known manner, for example by reaction of a diazoalkane of 1 to 4 carbon atoms, so as to provide the corresponding products substituted on the nitrogen atom of the sulfonamide group with an alkyl group of 1 to 4 carbon atoms; the hydrogen atom of the same atom of nitrogen can also be replaced by alkali metal atoms such as sodium, for example by the action of agents

Alkal Jns basic.

  This known method of condensation of the products of formulas (II) and (III) has various drawbacks, in particular poor yields. It is generally believed that the presence of acid acceptor lowers the yield by the fact that In addition, the use of an acid acceptor makes the isolation and purification of firal products more difficult and more expensive.

  An object of the invention is to remedy the inconveniences

disclaims known methods.

  Another object of the invention is to allow the preparation of products of formula (I) from reagents of formula (IV) of technical or industrial quality. The formula (IV) is the following:

C B 0001 (IV)

D O -A

  E- This last problem arises all the more in the

  practical, that this type of acid of formula (IV) is capable of

  tible to contain many impurities because of the

  number and nature of the reactions used to

  Thus, by way of non-limiting example, it can be stated that acifluorfen of the formula ??????? ??????? Cr (F) ## STR2 ## may be prepared by coupling an alkaline metacresolate with a 3, 4dihalogenotrifluoromethylbenzene followed by oxidation of the C 113 group to carboxylic acid group and

  nitration During such a sequence of reactions

  tions, the number of isomers and other undesirable compounds

  will multiply and in acifluorfen of ordinary quality

  However, a large number of acids are often detected, more particularly 2-nitro-3- (2'-chloro-4'-trifluoromethylphenoxy) benzo Yque acids in an amount easily up to 16% by weight, 2-nitro (5'-Chloro-5'-trifluoromethylphenoxy) benzo] ethyl and 4-nitro-5- (2'-chloro-4'-trifluoromethylphenoxy) benzoic acid, the latter two acids being easily present in amounts of up to 3% by weight as well as a number of other acids, in an amount which may also be up to 3%, but this quantity is often lower, for example less than 0.5%, for example 3 -12% acids. Chloro-5 '- (trifluoromethyl) -phenoxy-benzo [br] -3'-chloro-4' - (trifluoromethyl) -phenoxybenzo] no. onbluq Dai 91 T Innb op (, II) alnul IOJ opa T zaar uol: lt, u C 2 oetlp qua 2e unp uolia Llgi el ap saxissl sazaindia T SC sal aldmaxa aud luos saieindmi sallai aa -splaindu Tp spiod ua Z OC Vnbsn C quatallalla ail the splod ua% OZ Vnbsn C juuuaquoa ai Tp VI 50 3 4 allelaisnpul no onbluilaal 91 T Ienb op (II) op aplz) up ainue 13 oleq a l (III) almazol op ap Tuuuojlns al ze Au a TZ-ega inodl aj Anao ua, aiziam OC op luoiluo Aur, -l suep 'to Tq Tssod: Iuamalz? 29 lso TI (II) almajoj ap aanua 2 olutll Da Av '(III) altaioj op aptituuuollns np uo T: Izuga el op sanoz ne gs TI Tin lnjau anb ataaui el isa Tnb uo Tieue 2 oleqp jua 2 e unp aplel Q (AI ) alnwioj op ap Tav unp uo Tieug 2 oleq ied rice gaudgid 919 v (II) to Tn Luioj ap ap T fu ainuagoletl -l fuo T: iu-a A -Ul uo Gpgaoid hp nd aaagjgad aluelic A aun uola S -jouuo Tiaugi na Tl Itu np asnaze U amioj snos the aansam c 4 a a-ij nu gujtuilq isa uoi: lavgx el lueinp owmol as Tnb (atib-Fxp Xqoletl flat, no ap T:) eapúil no) apfaep ainugol OZ -L-qr anb a law aun i: the (uorivinxolilano) uo Ti -violt ID ap oauaagjgjd op 4 uol IL-uagoloqp jua 2 v unp azuos -Cid ua lapiiib TI astqd ua) ii: ia; ajja: Isa linb at ua esligi -aviva duel ppgzojd U is suflua Tjlu U Ts soil juo saloqm Xs soil ulisibual suvp (111) alaiwioj op ii) ftt Leuojliii yc aa aa Ac (II) alntujoi op opraep) Xllugljol Lq an IT 229, x O ITL-J e Tsuoa Inb uoTlua Auil u O jas; Iplzold does not have any effect on it. luoxiji ,, aedde saa L lue Au sax-4 tiua glaind alqrej op (, I) almajoj op sijnpoid op i Tjiud 94 aind auuoq op (1) ilntajoj op siltipoid al) uolluied -qid v T aillamiad op Duop isa uo Tqua Ku Tl op inq uft e T

  lauazuaqoxi TulXxougqd (I Xqlgutoaon Tj Taz) -, - oaolqa-, Zl-.

  alan Tsule lanb Xozuaq 59 L 9 S z

  up to 20% in ponds and possibly

  These impurities of the acid of formula (IV) are mainly products of formula similar to the main reactant but differ mainly in the number and the position of the substituents. These impurities are therefore essentially compounds having the group substituted in a variable manner, or even the group

C

substituted in a variable way.

  The process of the invention carrying out the reaction of the products of formula (II) and (III) is therefore practically carried out in the absence of an acid acceptor; otherwise

  the presence of a solvent is optional.

  A sub-family of products of formula (I) for the preparation of which the process according to the invention is particularly suitable and advantageous consists of the products in the formula of which A is the NO 2 group or a chlorine atom; B is a halogen atom, and

  especially chlorine; C, E and G are the atom of hvy-

  drogen; D is the CF 3 group; R is an alkyl group having most often 1 to 4 carbon atoms, especially

C 13; W is -CIL =.

  Preferred reagents of formula (II) and (III) are

  obviously chosen in such a way that the symbols

  in their formula have a meaning similar to that just given for formula products

(M).

  Ise U 014 DU 91op el 'lu L1, Iosunoa, & naoua -jean' V.041 1 O SOUTH al Suep lppg 3 oid a T suep Zueuo Alaqu, (1) (111) '(II) alnriaoj ap siznp- oad sop uo illsodmozap ap aan, -ejadmai el k ajnaijpjul sanall Te ls Ise ainlvagdinal alloa 9 j 9 u 92 Ise I tnb airisau u the inj u ase naze 2 awiol snos lauuo Tizeai nllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllll if not a quizj anb Tapj qort-q apl) v no aplau p ainuq'uloreql anb allai oc Ise ai Anao ua S Ttu Ise uojjua To Tj uolas apgzoad al allanbel ainjuagdiual el tiuouituapgzaid i Tp 919 v IT autuo D lauuo Tizeai TIOTITU ap Salcao- C sjjnuilans sol iai T Agp Tssne jamaad -And f alsarilnulpul: allaq 3 al Q gpgaoid a suvp inaleqa op qaajsueil inal I Tata çz uli oillaaaad op aiib-F: IL-ad a 2 t, Zue Aul e aliau T 3 uv Alos a P -) 2 usii ,, j -sluc, & jos siiialssi-fd ap auulgw a zas Tll: ln Tssnu: 111 aduo anb Tai alljq Tuun aldtaaxo jed no auezuaqoiorq D al "or Ltl: i,) ozultia Tp-Zll al lauatan :) al "saua T Xx op sa Vuergta eil Isoual Xx sar 4 ouan joi al lauezuaq al oz anb tai uou no ajol 1 z) lanbr: i T-, uloze no anblit-Id Tlae "ainqauaojl") and a Laixa ali and uufi Duei op aanluagdmai and 2 ina Tagdns uorl Tj-tntlgp jul: od a juv Xv aliaur luv Alos a suup eliossjp garlic C fustie jua Anad sj-iq D Lga salt anafigilii o'3 LIDúzoa unp çi um% uiilerlilslp aud lauuoriaugi a'ui -Iptu tip Cx) dn Dqx aj 12 siole inad Il - uoliacai el inad qa A-ros op ty ja "xi", the "xassudap saole jnad (II) api-ai, p ainua Voleql Qioddui aud ai Tulotu lioddra al) S 2 axo avaer ua isa UOIIL'Ug; 3011? Ttp: Iuaui ,, lolibsloqç the El (aalui 01 luawaleigua 2 aliv A (11) alntuioi op ojnuaojeq IQ ijoddui avd uo 13 uoqqu lua Vep wingjou lioddui al suo Tq iodoid itz) juos sj: j:) vai saz) ilua , tnos sn Id al l T It the 640 arqua a Duaig Igidop IZIT the 810 arqua s Tidiaoilua La) - l-uagua 2 isa (111) ap-la (Il) op ajjuloui lioddea al -glajg td- Isa úID ( O) dl sailnep the z 13 z os laos 4 c-xiiija (O) du) d4 ú 1310) d: roominad uo Isalqvs Tliqn uol: i Pua'Joluqp squa 3 th salt -iciavd 59 L 9 S z -sluenilisqns sau, ap mou received (S; 21 from south not la) juv Ae sluani Tisqns saporor 4 Tsod vl quenb -Tpu T sajjjjqa sal lue 5 eld na si Tnpoid sal zau Tsap inod auuoxeso, 2 ue ainjul Duauou Pl sli'n e no aa Anao na as Ta Ski 611-to O aouloo to 4 u alluom the uollua Aul I quaj: lsnlll: j 4 d 4 ltukt not al ITI Q squuop sque A Ins saldmaxa se-1 oc ap; apiiavuojlns up azuosgid na sim a JI 2 P JUUAV 19 TOST

  help "1; -juuo-il-augi: Iuu, & Ios al suu-p ni-r-s u T ga-edaid -

  no tuoile T Siind sues iniq leigl V glos T -

No. 49 TI Tand the plos T -

  I have 12 days II s.inas Xluleo sap ai Anao na aiijbti Tssne znad uoj the Ilii; Do you know that you are a student? Do you want to know that you are a student? Intutoj ap aplui? (2) (2) (2) (2) (2) (2) (2) (2) (a) (2) (2) (2) (2) (ii) Aui & itu 4 fui gava -gjd aj 12 inad (II) alniaioj ap -), pfaup -3 uv Alos non unp uoi 4 uppa ied uojeaqjfj alla issne inad no uoli -vaj Ij aun V luamaleigug U liiipgj as uoflujgdn Dga alloa anb çi a 3 jos na uokinue 2 oloqp lua tul suep arlnlo,; u T isa ieu -uu TS i Tnpoid np uoîzleaednugi ap apom np CITDT Tdtals el x Ld aii 2 uris 1 pas uoiaui To Fl uolas gpgjoad jj Your na nuuoa ua Xota znol aud -ajos T azig: Its,) d (1) alitziioj ai) iliipo-id il uoiiz) L > 9 i op uij u: l 01 ID 10 çi 10 09 ajida as Tadwoz lua Luastia 2 catteàe isa ainjuagduai el i (j úcT V inoq rnb auauni np sua al suep luatualuiauds) juu Alos ap azuis Cid na lj OZI la 09 ailua usiidmoz isa allarluaie 3 gid aanze i 9 duial el ': Iue Alos ap az> uas (IL u: 1 -l) Ogl qa (L a 1-jua as Tidiuoa iuatialui Cug 2 zuop lsa eq -: I Tp ij: 19 Qqp ela 3 atiuoa spxa ua Uo Tieua 2 o Tettip lua 2 el aed anlil -suoi aaq 2 1 sinaj Iv ,, 3 1 itad rtib luualos ai ap uoy: ll-lInqp & p uinivagdwal el Q ale 2 a no aina Tiejui luariasni 2 eluv Au

S 9 L 9 S 2

  1 seen 1 a i a V 1 j u 1-1 e 1a a -1 1 c j U ') J13 a a J a) a J il D 11 1 13 E? U (j) C) N d) (a) O (a) z E? z he in O JS aL k, 1 Ci) a 0 ri 11 3 -1 O r, a -fil4 S u Oa up L jl a tg zua-iiaail ajou CO ') The supp jiqlqo ua -auanfol ne Aej: ## EQU2 ## (Gold Za53 1-yy-1: juepuad u C silosgjjtiela s-jlauuorijug 1ajuvrgu al ap Ula c ap la c 1:) (O), The following are some of the following questions: (a) (o) oa ap faer ap aliiiolq D a,) (ali (, "ir Raid aa f ea E inu aribrzau Uua aaueuosai jed la a Uniligated is the ilneoid of D ap ns i nd-i Z Z uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo uo "" un un un un un "" "" "" "" "" "" 4 '10 U (-aaanfoi does not have to be aaqlij isa auto glfdraaad al lauaniol ap u D oç ap uoz 4 upples Qad VD 06 V janaq r 4 uepuad uoilellàe snos gjjnetio qsa lauuor-4 zegi; auelqu aJ -ar ioqdsocid ap aaniolip il isa rnb ela (O) d o u u o u o u suip aapsuadsns ua spa quos apr, uuuallns aueqlgu ap (ali ainiolula,) (aloa V, 040) L 49 d HD z OSHNOJ ID Z z E z

1 U 3 + DD

  TDOD s 9 L 9 S z E -Mkoe jud agnoivigul jed agma Tjuoz Zsa i Tnpoid ea op aini Dnais el -3 00 ZZ lue Pu Oi & (IA) alnmúOS op gap Tmuzuaq l Xuojlnsauetizeci-, Ioaliu-Z-lXxougqd (IXIIIDMOI op gni Tisuoz Duvlq ap T Tos unp (% ilc juawapuai alom tco 4 o) 2 54 EZ Tsuq lua Tlqo uo OIE lauenjoz ne g gul s Ind gai T Ij Ise giajoj qj Td tz; ad el gjuataassjp Tojjai S 2 ad VD ço l sauna Z leu -uoliaugi has 2 uelqu al allnuq D uo s Ind 4 ú 1 j (o) j op E: my LZ sainu Tta 01 ua siole alnoa, uo - apriaruojlnseuuqqgm op (a Tom) 2 46 ai Tnpoilu Tp iuv Ae 40.06 Q leuuo Tazugi has 2 uelqu çZ al aziod uo lassaa xnazug luama 2 e '"gp al anbsiol - aunjoj op i: ma T suep OTXU Ojqz op a 11110114 a op (alom -l 40) S 6111 op uo Tinjos In a new language, we have been working on the second part of the world, in order to improve the quality of life, and to improve the quality of life. Tu-Z-lXxougqd (I ttlgtaoj aplaep (a Tow 140) U 149 ú: 17 ald Waxa Nlia sud has 2 noieijuj jed agwjyjuoa Ise T: Ifitpoid av op ainianais v-1 -D, çl ZQ iuepuoj '(IA) alntaiol op "ap Tmuzuaq op gnilisuoa Duetq OPTIOS unsp (Z LB lu O ma Pua J l DI Qa CLTO'O) 2 96 L- Tsulv lua Tlq O UO ç / ç 6 aliqzg p ale 4 l-ae / au 2 nlai a Vuelqu 01 el suep gs TT Iezs Tiaza Ise nuolqo iniq al -3 as 2 galuaauoa s Ind Isainu Tta OC q Z luepuad xnljaa Q uoil Tlrnqel V uo Tzel -T Uu snos gliod Ise jouu OT 13 ugi aguelqui al 'al Tal Tuolp Of 4 pma OZ op Ic 13 (o) op op: ma Z op 02 UV Igta a suu P uolitilos ua sim juos ap Tmuuollnsouu 4 lgul ap (alow Zog O) 2 9 641 the anb Xozuaqoillu-Z-lfxougqd (I Xqlguoaoiiljlal) -, - oaolq D -IZI-OPT 3 eil op aaniolqa OP Pl Or ZO'O) 2 94 L 59 L 9 Sz

2546 I 6 5

  EXAMPLE 5 This example illustrates the preparatior I of benzanide of formula (VI) at the beginning of impure Plenoxyhcnzoic acid.

  purity of the starting Cnoxylbenzo Yque acid was 6 d 6 tc'r-

  in high performance liquid chromatography (PL) (abbreviated), this IIPLC was tested under the following conditions: column length 20 cm, tanitrile 4 minutes, lining of the plate on which we have grafted phase ine

  stationary i grouped annne (the chromatoprapbie is

  Partitioning between the stationary phase and the eluant is carried out in a mixture of 42/40/18 constant relative volume proportions of 2,2,4-trimethyl-naphthalene, 2-propanol and acetic acid.

flow rate 2 cm 3 min.

  The so-called product purity (the reaction was identically degraded in IIPLC under similar conditions except that the proportions of the constituents of the mixture between the d-butt was varied in the diluent. and the end of the chronograph I, since a ratio of 35/5015 up to 56/20/24 (gradient

5 hours).

  The validity of these chromatographic methods was verified by the use of standards corresponding to samples of each of the impurities 6 S taken from them.

Isolation.

  The percentages indicated below are

  The "technical" acid used contains 9% of 5-chloro-4 '- (trifluoromethyl) -6-naphthyl-2-nitrobenzoic acid of the formula (V), and 8.2% of the 3- [2'-chloro-4 '- (trifluoronyl) -phenyl-2-nitrobenzoic acid, and 3.3% of 5-chloro-4' - (trifluoromethyl) -phthalic acid. -4-nor trobenzoic enoxyl, and

  less than 1% of 5-1 2 '-chloro-5' -

  (trifluioromethyl) phenoxyl-2-nitrobenzoic acid, and

  less than 1% of 3-1 2 '-chloro-4' -

  rifll: oryl 6thyl henoxy) benzoic acid.

  38 g of technical acid of previously defined composition are suspended in a mixture of 100 cm -1 of 1,2-dichloroethane, 10.3 cm 3 (0.109 mole) of chlorine, and

  of thionyl and i cm DMF

  The reaction mixture is stirred under reflux at reflux for 1 hour after the end of the evolution of gaseous, and then concentrated to dryness. The residue (40 g) is dissolved in 75 cm of toluene and 10 g are then added. The reaction mixture is then heated with stirring for 3 hours at refluxing. After cooling, the precipitate formed is filtered off and washed at room temperature. The mixture is dissolved in methanesulphonamide (0.25 mol).

toluene.

  This gives 28 g of a white solid constituted

  5'-1'-chloro-4 '- (trifluoroemethyl) phenoxyl-2-nitro-N-

  methanesulfonyl benzamnide, of formula (VI), melting at

   C The structure of this product is confirmed by infra-

  The purity, as determined by IPLC, is 90%. The procedure for the preparation of compounds of the formula

D? N S R

  wherein A is hydrogen, fluorine, chlorine, bromine, iodine, a nitro group; -N = NCF 3; P 03 i 12 and its alkyl esters are 1 to 4 carbon atoms N U L 2, tiloit,

  N 2; a carboxyl group or one of its functional derivatives.

  tional; a mono or dialkylamin group; a group NII-CO-R 1,

  in which R 1 is alkyl or alkoxy 11 or mono-

  alkylanino or dialkylamino; an alkyl group; trialkylan-

2 2

  nonio, NLSO R o R is an alkyl or plibnyl radical NIICONIISO 2 2, or has the meaning Oej Ind 1 itue

  alkylthilo, alkylsulfinyl, alkylsulfonyl, dialkylssnl-

  fonio, cyanosulphonyl, hydroxy, alkanoyloxy, alkoxy, allkoxy substituted with an alkyl,: ycarbonyl, S11, troso, -SCIN, azide, CF 3 1- = N-P (OCI 3) 2, jacyl;

3, 4

  B is hydrogen, fluior, chlorine, bromine,

  iodine, or an alkyl, alkoxy, alkyl sulfinyl, alkyl,

  sulfonyl, CF 3 NO, NHN 2 MCOR 1 oe IR is defined as (above, or CO N 112 C is hydrogen or a halo Zene or u N alkyl group or dialkylamino aplnbll Dseqd ua aonliajja juvig ua'cliega alfpel eapor 1 no al taaoïq D al isa -'c atao aq la 1 (j) alnji O jUT inod saanb Tpui suolieafj Tu'Ts sol quo sa-Coqji, s siailp sallaiibsal sol suep a In L 3101 a? Ap Tia-vuojlns aa , & e altiuiaol op apr From p ainuao-E Lil pz a a F 3 eo ilej uonb a D ua gsragiaeleu juulg gpgaoad i Tpal praise X :) no louoqx LD op sariaqe ç k Z op ouer Xuoqx L, :) IX-auilu lauo (2) L y op oo ry L y op suojc V 2 1 ap y L unatqa laj Kuojjnsj Xjju 4 al uij -Insl (4 lllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllll

  -sadiioi'Jmallatibilq uep no ououi4 ouoqiva-

  op SOLUOIV ç 2 Z av alxuoqjujlc 4 lo lauoqjtj al) saaole ç e 4 LI Lk-4 4 Uteè & 4 ké 4 and * IJP &, i A Iti-1 tio LAD O aui) JCI Cad op lopoi 110 Z) tuoxcl l ' a zolilalion 1 jopsatuoitsxnz) rsnld no one south sgn: lllsqns T quatuarlaitiuo Ag auoqiva ap saigoje t 7 k 1 op DIX-ile lualpui a no ouoqiva op samole juu va I Xa X Island no I Xua-: Ile jeajpvi a no l oi : jju sadnoi J no sadriox Jno praised 2 c) satirical word sina Tsiild no a ard anljlsqns juatuaruanl -uo A; lal ugrtl: inoal plt d 4 al, uatidadnoz 2unqsa aq inod saauuop suorieu Ij Tu 2 Ts sap aun ad Ltoj 2 a no JJ: Iozep, yes, an isla, tl aarlbrpulep 9UHUUUUUUUUUUUUUUUUUUU 4U-OD-11 11 lition 4 z lIN 'cj D,,,,,,,,,,,,,,,,,,,,,,, 2 a no aua 2 oxp X, he / she / he / she / he / she / he / she / he / she / he / she / he / she / he / she / he / she / he / she / he / she 6 aji (o: avlns larle 2 ojvq fol Xuojltis IX, ilu lai Xuijlnsl no l ai) OT the atuaiqal al Iion-rj al isa çj S 9 L 9 sz Zlaz No Zi oo no Eiad no úxq (o) d no ú i Ddcc no ID (O) d Ise uo Tiruagolelp iua 2 ul anb ai ua alsra 2 1 suo Tzea Tpua Aai sap aunj uolas apgaoij (g 21 a adnoig al juuiaodwoz S 9 soduoz sap juatualedraufid quos saloindtal sol alib ai ua as Tagiaule D (9 uorleulpua, & aa el uolas apgaojd adnoj al 3 uviiodtuo DS 9 sodwoz sap luawa Tudlauîad juos inb sglaalidu T Sap quarquoa (11) a Intajoj 01) apyzep ainua ' Uo IL-tjal oz anb ai ua (ç ueri Lalpua Aai el uo Tas (9 spiod ua X OZ V inajagjul ajuai -gjgad op 4 sprod ua% OC V ina Tagjur isa (Il) a Intajoj ap api Del) ainug Uoletllopsg: iaxndtaipxnul 'al anb aa ua qs Ta -glavaez UT suo Tiez Tpua Aai sap? un uolas gpcaold (ç Irl úil :) aauaagjgad op auoqana op sawole 1 op aj, j adnoj J a isa a anb ai% ta Ta -gi Duiva (CUT suo Tivzfpuaax sop aun, -1 uolas qp? 3 Ojd lajolita ap auo-1-L, Ise X la, Ire, adriau a: Ise U la ajoltlaop ataolul Ise q anb ai ua qs Ti 01 -j Of 1 U 3 (Z no r SUO Aier PUO Aal sop ounj uo Tas a pcuoid (c = Il :) lse adno 12 a Ise at lauivoit) ',, tp autolvl JUGS 9 la: -j the a' a U 22 -011 1 tj'pa; Io: IL, a: Iseal 10 T, 13op 110z O in the V ab a ua gs T 91 91 ie j j j el el el el el 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 91 The injustice of the 9th century is that of the Jews and of the children who have been in the world since the beginning of the year. xd ua s 9 L 9 çz 1310 çl 10 aa aaa azaigg çz -C Id op & D 091 Za OL OJIUO as T Idtaa D isa oanieigdoui el anb 33 ua (T UOTIDDTPUD, & Oa VI uolas alpgaolj (91 Olttaa O ua sl'a Zuu A-108 "P u OT: 11 'lTn (igp aanlt, xedwzàl er 2 a TL'29 110 ainalaglu-C 11 juvatj D 2 sen al 4 la (1) la (II) (III) a Inmioj ap slînpoid Sap uoïllsodmoaal ) op oanqualdmvl el 2 oz ajnajjqju isa a Tl auaollavai ainivagdetai el anb ai ua asla -giauluu (1> 1 2 1 suollnarpua Adi Sap aun'l uolas apgaoal (I 0112: 41 U a no 4 ajolqz or no gioltia 1; 3 nb T: I Lwoze no onblietid T Ie 1 aptb 'c I a isa: Iu L alos al anb oz ua aurliliuani (Cruorlu Dlpua Aal VI uoras gpg Dold (j T * UI : t 2 ua u t ue tt -91 Z> UIUD (Zl UT SUOTIU 3 TP Ua A Oa Sap a Unl UC Ia S gpga Oad (CI at 140 Oulu aauaigigid op 'oz the leo axlua sfidtaoz isa (11) aplzep aznua Vo 'U lioddea aud uofieugio Lettp 1 ujjt - p axivroa jauddui al anb ai ua 9 sfi 01 -CIZUJUD (Il e 1 SUOIIUUJPUOAUI Sap aunj uoras gpgaoij (ZE Ill the 610 aalua aiaagsgid op Izel the 8' o aizua sladzaoi isa ( It is also important to consider the following issues: (111) APTAUUJTTS APTTAUUJTTS ARAFTA JANADADA AL ANB ASIA-A-GIJEAUI (01 2 1 suo Tauz) rpua Aai Sap aunj u O las apg Doad Inaldaujep ajuasqu ua ai-2 do uonb ai ua at Is Ti -qijejez (6 UT suol :: I This) aa Sap aunl uolas apgaoal (ol úla (j) d isi UQ Tj Uuî 30 j 1? (jp juj 31 -'j anb ai ua asiaglaviva (a Ull M 3 TP Ua AOI DI U 01 ag ap 3 01 J s 9 L 9 5 z