PT87938B - Processo para a preparacao de acrilatos com actividade fungicida - Google Patents

Processo para a preparacao de acrilatos com actividade fungicida Download PDF

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Publication number
PT87938B
PT87938B PT87938A PT8793888A PT87938B PT 87938 B PT87938 B PT 87938B PT 87938 A PT87938 A PT 87938A PT 8793888 A PT8793888 A PT 8793888A PT 87938 B PT87938 B PT 87938B
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Portugal
Prior art keywords
compound
formula
acid
optionally substituted
compounds
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PT87938A
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English (en)
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PT87938A (pt
Inventor
Geoffrey Ross Cliff
Ian Christopher Richards
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Schering Agrochemicals Ltd
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26292482&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=PT87938(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from GB878716392A external-priority patent/GB8716392D0/en
Priority claimed from GB888807388A external-priority patent/GB8807388D0/en
Application filed by Schering Agrochemicals Ltd filed Critical Schering Agrochemicals Ltd
Publication of PT87938A publication Critical patent/PT87938A/pt
Publication of PT87938B publication Critical patent/PT87938B/pt

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
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    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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Description

U 0 O i ) s t e p r Χ.Ί V.· u t ;i : i i d to;. éu I 0 > C e p t e e e n te i i i d r o j e n i. o o u i 1 o , 1' — s L* s o n r i 1 3 i ) n c e do o n l ·Γ; ) - > s C Ú , 3 C Λ C e r] t úl 0 > . t l d 1, r c s e n t; a o , s , 7 \ 2 • / I ^ | a d t 1 í ^ - k -1” ) ',1 0 u i K 1J .o ^ ) e .. ue :V' L 0. : ) L sô e n t d: ;L: :· t o Γ 0 -Vi Γ 1 1 0 o 1 3 i o :i a 1 , e n t a s u i)t L t u i i) L J Γ 0 -C i cl i C 0 op e i o n a 1 ,. 1 m e n te s U V; .s t i L- li í m b> t setor o-cicii i {tinj h-J O C p· - i O ilJ i V π L J S Li id -3 L 3. L U i li 0 , alv. aeuilo 0 _ cio Π a 1e SUUStitLli d o , a 1 ,. οχ;;! 1. o Oj-cionn 1.5 o u t e 3 u bs t L tu L> ic, - 1 51 1 tiieno si ustituido o p c i o a 1 ;e e n L tí s u u .3 c i l u i e 0 , : iOtero-ci 1 i n e η o - e t i 1 o s ;i i) 5; t x t u ido; 0 a
UlJ n : 3 r 3 S '3 3 3 t a c o 3 ,) r o 3 n a i a o r π l f 0 i o ] , , .. r o — ! .s e n t 3 ou α a i 1 u o a cionai- santo au i.> a; t i L u i d o ; o u b) w e .:J for;,:d!.i aart a da u:r. η η o 1 de c La cu eu aeis
[; Γ O S ue pode ser substituído o pode conter outros ii e t o r o-a t os o s , s p e ciaio it c e aaoto , p represente j ou 1, :. o n esmo cotr : nu i dos entre e J.j , sendo pelo sonos us .los , n e mi. or {1 :1; ~ -v í l ^ e ... l e . n t ^ -1 , 1' , ... v- , .j o , -.. ^ , e i. ( J .. ) . v , . .· t . ]. J rL·- ). ou .mm.: je . representa . ou ept jssíí:: :iu;o-:';;Í!), eLpiiic opcio;: eleeete substitui lo ou arilo o p ; L o n a 1. -O i í t O S U Í5 s t i t u 1; 1 o | o u ) r o s r o s e n t < i '3 O C (71 3 C m Γ ϋ ' Γ 6 b U ϊ 1 1 a 1;., ui lo, ..i representa lj , p e n representa 1, d , ..d*· , d i ( 0 ." , Si(t“), ou Si(ub“).; e d1 e a a ilie < i c: u i i. o ; rojiccsant a a 1t niio ou repr: s e π ta u .>. a e s o o anel o e opcional:.;ente substituído; adiçao a c 1 u o al; aa a eitos. u a 1li o r cocídos tos
_ 9 - coso isc isoooros in.livijuoi oóLi] o ou otilo . ..3
:0.:::03:0 .3 0 i::vo::ç .o 0:1 ,1 ·., b u o s 3 u a .3 t U L . orupn:; a 1.j =: i 1 o :ao os :1:,.03 a 1; sj n l I o o a 1 q a i a i L o tf:? toes 0 sois aioooo .0 0 ;o contes : i s 1.; .0 n t e 1 O 0 X 0 u o . υ a o . -J o 3 u j s t i L u i (i t 3 3 (, li a :i d o 3 r a 3 e a t a a aa u a 1 α u . , 1- LL ,:o αΐ.ραχίο, alque ail 0 0 u a i q u i u ido, en .,,10 33:,3 a t o:.:o s uu dal o 0 é n e 'J , C U a i c o x i ( u o r ex et:: u i. o a e i c ti a t o::: o s e 3 -: r . tono), b alo-a leo X 1 ^ [/ o r axes. P 1 o d i 1 1 1! ο Γ 0 - 3' : e t o:: i ) , d i d r o :: i , z 1 uil- L 1 0 , 1 í; :i1 :t c o p c x o n a 1: e n c e a z b s L i t u x ci o , ca: b o x x , .; 11 c <j x i - c cr co.n i .1. o x i x η o 1 .0 c i 1 o xi a ar i 1 o . d a . r u .- o s -'rito aa i :: o t i .. i . - · 1 · 1 t~ d i' c o .j ‘.i i' 3 L i L u 1 η o j a '.j . O 3 i 1 : a a l o a η o o ,
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Cl a s c r 1 c c a rno n i i 0 f 0 s i ·.; u i a ala a n r j ο η o . •j UM 0 u ά O a u\ a r u Γ;'. o. d anel poce .ao.: substituído tie :: 31 r : t o í: e : i i L o e :: as n e: . : o t . t u ρ o s o
Co a ai lo" o n ,; j. o p a o resíduo u a acicio s u 11 o n l c o te 3; íostoro e t az bar: ue ácidos c a r b o x i 1 i c o s . so.o d e pref e ó atoais cie careono. os a rapo: po: ces que pode::: iorsar u:a anel, por e:cespio podes: forcar u: mel sorfolino ou piperidino. Os grupos is i n o-rae t i 1 e η o podes isr substituídos ao a toso de azoto e no de carbono. Os exes- aos que c o n -> .· r u η o s a c i 1 o x a i i ? 1. o \) o a o a i a k iO G Π L L e 1 H* O o o d 3 sor :· Μ l b s t i t Ll X dl O 3 1 (i u i lo o a d o i s 3 Ll b S t í t Ll Í 11 - f BAD ORIGINAL Λ
pios de substituiates no átomo de azoto englobam ari 1 o a alquilo. Os exemplos de substituiates no átomo ca carbono englobai:: afilo, alquilo, alquil-tio, alcoxi e ciano. <J ίϊΐ grupo particular:. ,;en t e preferido de compostos e aquele em qu e n representa 1 > P representa 1, m representa o, . repres sn ta Ci: ou f.:, £** - j O ,; representa :netilo , X representa S e lí representa hetero-arilo. .
Os compostos da presente invenção sao particularmeate valiosos como fungicidas , especialmente contra as doenças f un g i cas das plantas, por e x e m pio i 1 d C o c parLicul a r ,:i ente 0 .li í ldeo pulverulento de cereais ( L, r y s i η h e qraninis) , m i 1 cl e o penugento d as videiras (PI a s ::i ooar a vi t ico- la), ferrugem do arroz ( P y r i c u 1 a r i a o r y s a a ) , fungos vermelhos dos cereais ( Ps e u d o c e r c o s !> o r c 11 a he r ao t r i c ho id es ) , f er ruge a; das folhas do arroz (Pellicularia sasaidl), bolor cinzento (Motrytis cinerea) . fungos da putrcfaçao (d hi z o c t o ni a solani) ferrugem castanha do trigo (Puccinia recôndita) , ferrugem da batata ( P h y t o p i i i; b, ota infestans ) e sarn a d as maças ( Ventaria i n a e <.; u a 1 i s ) . Os outros fungos contra os quais os compostos podeíií ser activos englobam outros mil d aos pulverulentos, outras ferrugens , e patogeneos gerais de origem i/euteromyce-te, As cor, yccte, P h y cor, y c e t e e basidomycete .
Us compostos da presente invenção possuem também actividade insecticida, acaricida e nematoci-da e sao particularmente uteis para combater uma diversidade de insectos, acarídeos e nematodes das plantas economicamente importantes, incluindo os ectoparasitas dos animais e especialmente iJipteros, tais como varejeiras, Lucilia serica-ta, e moscas vulgares, Mus ca domestica; Le ρ i d o p t e r os , incluijq do Plutella x y 1 o s t e 11 a , Spodootera littoralis, 1 í e 1 i o t h i s ar-mi g e r a e Pieris brassicae; Homopteros, incluindo afídeos como Μegoura vicias; Coleopteros incluindo vermes das raízes dos cereais (diabrotica spp., e.g. Diabrotica undecimpunctata) e acaros, tais como Tetranychus spp., que também podem possuir actividade herbicida.
BAD ORIGINAL 4
b e _i u m uetoco para combater as pragas (isto e , de fungos, insectos, nemátodes, acarideos e ervas daninhas) nur 1 ugar infestado ou susceptivel de ser infestado cora elas, o qual consiste am aplicar-se ao local ura c o cipos to de fórmula I A presente invenção também proporciona u:na composição agrícola constituída por um composto de fórmula I e:n mistura cou um diluente ou veículo aceitáveL e m agricultura. Λ c o m o o s: :ao r1 vi isente invenção pode englobar, como e evidente, ma is do que um composto da i n v e n ç a o . Λ composição pode conter adicional-mente u:u ou vários ingredientes activos adicionais, por exemplo compostos conhecidos por possuírem propriedades reguladoras do desenvolvimento das plantas, propriedades herbicidas, fungicidas, insecticidas ou acaricidas. dn alternativa, os compostos da presente invenção podei:! ser utilizados sequencial mente com um outro ingrediente activo. 0 diluente ou veiculo na composição da presente invenção pode ser um solido ou um liquido opcional m e n t e em a s s o c i a ç a o com um agente tensio-attivo, por exemplo um agente de dispersão, um agente esulsionante ou um agente humectante. Os agentes tensio-activos adequados anglo-bam compostos aniónicos tais como um carboxilato, por exemplo un carboxilato metálico de u:a ácido gordo de cadeia longa; um b-acil-sarcosinato; mono- ou di-esteres de acido fosfórico com etoxilatos de álcool gordo ou sais de tais esteres; sulfatos de álcool gordo tais como o dodecil-sulfato de sódio , octadecil-sulfato de sódio ou cetil-sulfato de sódio; sulfatos de álcool gordo etoxilados; sulfatos de alquilfenol etoxilados; sulfonatos de lenhina; sulfonatos de petroleo; - 5
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i su1fonatos de a1qui -benzono ou sulfona ;<e::i pio sul lona to do f ο π a d o - c o n á e n s a ci o d
-condensado de íormalrieido; ou sul lona tos ruais complexos tais z o ra o os sulfo natos do a n: i u a , por axa; ι p lo o p c o d u t c de c ο π a a n -saçao sulf onado de ácido oleico e da h-r.ieti 1-tau r ino ou os sulfo-succinatos d e d i a 1 q u i 1 o , por exem pio o sulfonato ou dioctil-succinato de sod io. Os agentes nao i ó n i c o s engloba produtos de condensação de ést ores de á eido gordo, álcoois gordos, amidas de acido gordo ou de fe nois alquilicos ou a quenílicos gordos substituídos c o m 5 x i d o de etileno, astro , por exemplo estores da condensação do tais pio 6 s tar e s cio a c i d o g o r d o s de ateres de a 1 c ai poli-hicirico de acido gordo Ce sorbitano, produtos e s t e r a s cot; oxido d a a t i 1 a η o , por e x e m gordo de poli-oxi-etileno sorbitano, copol íme r os do bloqueio de óxido de etileno o cie óxido de propilo no, g 1 i c o i s aceti-lénicos tais como - , 4,7 , 9 -1 e t r a - m e t i 1 - 5 - d e c i n - 4 , 7 - d i o 1 , ou glicóis acetilcnicos etoxilados. os exemplos de agentes tonsio-activos cationicos engloba,,) por exemplo, ura mono- , di-, ou :>ol i-ami-na alifatico tal como um acetato, naftenato ou oleato; uma a m i n a c o n t e n d o oxigénio t 11 co. λ o u.a oxido de a mi π a o u U .:1 poli-oxi-e tile no-alquil-a aina ; uma a r. ina 1 i g a c a a uma amica preparada por condensação de ur a ácido carboxilico COM U i:l 3 di- ou poli-amina; ou um sal de amónio quaternário.
As coraposiçoes da presente invenção podem assumir qualquer forma conhecida na especialidade para a formulação de produtos agroquímicos, por exemplo uma solução, uma dispersão, uma emulsão aquosa, um po para polvilhar um revestimento para sementes, um produto para fumigaçao, um fumifico, ura engodo, um pó dispersível, ura concentrado ernulsionavel ou grânulos, além disso pode aoresentar-se numa forma adequada para aplicaçao directa ou como composição 6
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u:„ po j.ara polvilhar o constituído por ua co;::posto ha prossnts i n v a a a a o i a L i ..ia-.: e n t o misturado a t r L t a c a a o ao,., via <d iluent e pulvarul·.1 r. t o soliao, por o:·: o a.· lo a a. u i i ii o . solido 0 r a a u 1 a c c o n s l i t a d h o por u:o:i ij O ;-j t O hl 0 : j r c a a ri t a i n v c n a Λ0 hi a O 0 i .lho 0 0:1 1 i 1 u o n tos i - d c n t i o o 3 a o 3 d! U c S 3 [) 0 Ci a vi u t i 1 1 z a r n o 0 o p α r o r. , o 1 v i 1 h cr, ma L O Z S G a pran. u 1 α c a o í a i 5 t u r a. 1) a - u α 1 o ,vo to d os o o :i:: v c i d o s . e r n a l i v Ai i) 0 u 0 s o r t o i; s t i t u L α o ,ol o i :p,r c v i 0 Π t 0 a o t i v o a \j 3 o r v i d 0 0 11 a a s o r v i a o í!V!a d í I n t a ir _· rauulo . L , 1 O L o :: · : — j 1 o te L L "i 3 i ' 3 1’ ai 1 ar f *· · L: ã a: 1 . i l. a o a o r L i. C ϋ L cl 3 0 0 c : 1 1 cari o. A 03 CO:,O^OC1V 0 1 V, , C ai ; 1 li 1 G 3 Ou 3 a o c ο 11 s t i t U Í u 0 o U 0 L Siu il.v.ente pelo i n , r a α i e n t a a a L i V 0 õ ,· Γ.. L 3 tu ta ao;: n i i a j a a t a t e r isio-activo ade,_uaa o a p o L u a 0 1 1 U 0 Γ1 t 3 ca o o i n o r t o tal c 0 ..i 0 o c a u 1 i r; o . outro concmitr a d o a (d e p a a do 3 U ;or, centra d o d c s ii s ρ a n s ao 11 u i d i f i c a v e 1 nu a se ior ;i; n por tritu- :açao do C 0 auosto c o a a,, ua o lí a o a <3 u 11 o 1 i u u i d 0 , u o à ; 6 Γι t o humectante a ua a acato dc susoensao. A concentração Ao ingrediente activo na composição da presente invença 0, coco aplicavel a s [) 1 a n - tas , esta p r e f e r e n c i a 1 n; e n t e coapr csndid a entre C , 00 1 e 3 , G por cento er.i peso, especial:. ente entre 0, ,01 e 1,u p o r csnto 7
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..O j '· C lOúO 4 λ > c a s a U to 1 Λ V o n C. O O .1 j 1 1 o e o u u o 3 t o p o c α 1'; o ;i t o ua ocuanteu, .iuntuaj ou ;.o jgu :í d 11 n t . ..este ..o ::o , ό j a o licor-s e o composto α i r a c t a.: e a i:; a e s o 1 a v 1 ; 1 a a : o i. a . u a a ;. a . a L o p o s s a :o:itfol.:r o d e s e η v o 1 · atacar a se.a ente. .peando se tr·· a p 11 c a r - s e o :o :;;;osia activo r,. i t a s a a 3 ] e se ;a i s t α r e ί a t i o ,ior a s :i e r s o o , ·., o r a is a ars a o n t . es te ... o e o, c; 3 U o solo a n t e s ou Je 0 0 i d 3 c o p 0 S t 0 0 c t i V 0 a o to da i 100,0 3 G U Ό 0 0 o 3> a S 0 i. 0 d í r e c t a m ou to , ; o :i pa L.] a a r i r o c oSS 0 U 0 C o ;; o η ο I o , ;3 o o o O .3 p a for..: a .3 0 1 i d d: G 0 7 f * r, o a o e soo te . > . O 3U -.3 S s sem.ee t e s . .. i G · U G Ο Γ ica com p r e e n r; L G 31 OU t r c; r e n c i a 1 oen te o n t l o o,l a c t i v o u a r e c ca...ent ^ s ao ou o 1. v i i ,, ó l η 1 o . _ Lt 0 a a p a r 3 G G G S o 1 c o u P 1 , 3 0 0:0 G 0 -i 1 ti !_i \J ; ; L 0 t G r i d o .d e e ;; 1 i c o ç a o 3 pa i o u o i: e r x u o u u a ,m: a ç a o o a a s p e r s α o foi i a : r a 13 a t e importante a obtenção de a a ao; u; . c e ii j ο ο ί. n r e 3 1 a n t se lavra iase rias o-o no mesmo -o . υ r ç u o -ia a o 1 i c aç:: o adequada a a ,G5 e 20 por hectare, .sais 10 .1 ·, o o r h a c t i r e .
alternativa poi O U Γ U 3 1 ;i Π L i , U Λ V -' i O G G :i to U o o. o s co 0 3 G L. 1 3 0 0 0 ! i 0 t: . 3 0 ί 13 13 0 0 31 — S J too I í ) ao bua os nos p ci o e i r ο ί estádios de .· 1 e s e n v o ivioento de planta z que e η o s s a altera qu a a p 1 a n t a poda ser o eis grav d a n i f i c a d a . Λ a s n e r s a o o u 30 pod e conter cu η v e n i e n t e mente a 3 n t *3 li i -ia r o i c i a a p r e — ou p o 3 t — ri o s c i n e a t o se ; siderar necessário, dor vezes e nraticavei Ura i , a s piai 11 a s a n L 0 S 0 u :! u r ante a p 1 a n t a ç a o , p o r m -* o η .lo uln anuo as r a i z e s n u:: a conposiçao s o 1 i d a ou li 4 u c‘ . a de a < •p u a a t :· o se a nlica o c o .à o o 3 t o a g tivo d ifccta; e n t e sonro
a planta considera-se adequada unia proporção cie aplicaçao compreendida entre 0, U1 2 10 dg Por iiectare, de preferência entre 0,05 e 5 dg por hectare._ S - BAD ORIGINAL β
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Os cor.;postos em que .·; representa r>o o u 5 o .j ρ o u θ μ ser o o t i s o s por o x i d a ç a o c e u r c o m ρ o s t o e m q u ~ λ representa S, cor.; um a en£s de oxiclaçao adequado tal corro o acido aeta-cloro-porbenzoico. Os outros processos sao evidentes para um especialista químico, o :::es;;;o acontecendo com os métodos p <U L Cl ϋ t* c j) a i 3 Ç C 0 de : .catariais de partida 0 í : i t 0 r mediários. Os exem i o 1 o s ta m. be. |1 (j. 0 f aonstran a evidência d i v e r - sos metocos para a p reoaraçao da coupostos da presente invenção, sucedendo o mesmo em relaçao aos materiais de partida e intermediários.
Ilustra-se a invenção co::. os exemplos seguintes . cs estruturas dos novos compostos isolaaos 1 o r a m confirmadas por análi.ses elementares e/ou outras análises apropriadas. As temperaturas apresent a-se e :n jraus C. EXEMPLO 1
Dissolveu-se o.- tolil-acetato le e t i l o (IGO g) numa mistura de formato de metilo (4o0 ml) 0 de d i m e t i l - f ornamica (200 ml), ndicio nou-se a solução a ur. O k_i s u S p ensao de iii jreto de sodio lavada con gasolina (cerca d e 3 6,5 g numa dispersao em oleo a 30L) ci: d l ,.i etil-f or.-.ami d a ( ÍUO I ) com arrefeci mento. Depois a g itou-sc a mistura a temperatura ambiente durante a noite. fez-se a evaporaçao do e xcesso d e formato de metilo e da maioria da dimetil-for- m a mi da e adi cionou-se agua (500 ml). Tratou-se a mistura cor, eter e separou-se a fase aquosa, acidificou-se e extraiu- -se com éter . Fez-se o processamento do extracto de acordo com u;r. processo convencional para proporcionar um oleo castanho. Dissolveu-se este óleo em. tetra-iiidrofurano e gota a gota adicionou-se a solução a hidrato de sódio (15,5 g de uma dispersão en óleo a 80%) em. tetra-hidrofurano (50 ml) com arrefecimento. Logo que cessou a libertação do hidrogénio adicionou-se iodeto de metilo (35 ml) e aqueceu-se a mistura ao refluxo durante 5 horas. Adicionou-se metanol (5 ml) e
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u m processo :o n v e n ciop.ai para proporcionar ( Z ) - 3 -e t o x i - 2 - ( o - -tolil)-prop -2-enoato de m e t i1o, p.f. L·; 7 O ‘J ó “ / 'J Vm . Jissolveu—s este produto (1G5 „) em tetracloreto de c b ο η o ( 1250 m1) - . i d i c i ο π o a — s e > “ b Γ O i \ 0 3 U C cinimida (159 J ^ ) ÍJ- [-; uteou-se a tara ao refluxo durante 3 horas. Depois a r c e t e c e u - 3 e 3 nistu-l e u c í a a - 'r a o e r e z se o p r o c e s s a m g i i t o cara ρ r ο ο o r c i o n a r u n: óleo castanho claro. Triturou-se o produto bruto cor. uma solução a 10 Λ de e t e r - d i - i s o p r o p í 1 i c o em petróleo leve para proporcionar ( o ) -3-me t ox \-2-j_ ( 2-br o mo-meti 1 ) f euil_7-proíJ-2--e noa to Ce πetilo, p.f. G7-90oC . Gota a gota adicionou-se 2-— m e r c a ρ t o — u e π z o t i u c o 1 ( 1U 1 , ò 7 g ) em tetra — hid rol urano ( e'JU r. i _i_ J coe agi taçao, a uma suspensão de hidrato us sócio lavada com solina (cer ca de lo ,42 g de uma dispersão e cleo a O O . j ) tetra-hidr o furano (200 ml). Aqueceu-so a mi s t u r a a o reflu durante 3 0 rn inutos e arrefe c e u - s e ate a t c a: p e r a t u r a am b i 3 n te. Adicionou-se uma solução do composto de bromo-metilo (173 g) e.a tetra-hidrofurano (1000 m 1) durante uma hora e agitou-se a mistura durante 5 noras a temperatura ambiente. Adiciouou-se t a t r a — !i i d r ο Γ u r a nc aquoso para temperar a reacçao e evaporou-se a i.iistura. vez-se o processamento do resíduo por um processo convencional para proporcionar (l)-22!_ (2-òenzotiazoiil)ti o_/ -meti 1_/ f enil_/-3-.r.etox i-2-ρ r o penoa to de ;r.eti 1 o , p.f. 77-7c>°C (Composto 1) . EXEMPLO 2
Adicionou-se carbonato de potássio (25 g) a uma solução agitada de o-tolil-acéticvo (7,5 g) em a c e t o n i t r i1 o (12 5 ml). A g i t o u-s e a mistura durante 10 minutos ã teaperatura ambiente. Adicionou-se cloro-acetato de etilo (6,13 g( e aqueceu-se a mistura ao refluxo durante a noite. Depois verteu-se em água, acidificou-se com ácido clorídrico concentrado para proporcionar pl^ e extraiu-se com acetato de etilo. Lavou-se o extracto com uma solução salina, secou--se e evaporou-se, e purificou-se por cromatografia em coluna
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~ ι) i’0 Ο “ d Li C C ί Π 1 Y 1 Y S Y ,γ U 1 Y Y O ~ S d d C d Yi C Y Y O -'d O _ — Y. Y Y Y Y ·. t 0 “ ;j Y Y — xotiazol, ματ um ;:ro:eisu icêntico ao (i a a ; r i t o ao exemplo 1, jiara proporcionar 3-/_ 2-/_ J_ ( 2 - 3 e u x o t i x ;·. o i i i ) - t i o_/ . ·. a t i 1_/' í- T , . _ ...o,/. i On I i_/ --,--,:10 ui YY - L ji; J“G;lu , [; . L . j 1 “ u 2. >_< ^ o O ,.i , i; 5 l O .L ) . EXEMPLO 3 a urânio in.iu nora faz-se o refluxo ue 3 0 n ;·: o j_ b _ / tioie ι-2( 3.«)-ona ( u ,) o ia n i d r o x i c o o a roaio (3,2 j) a a áqua (4 o :.1). :»d iciou o u — sc cl o rato o o 4 —c lo ro - Mm — zilo (o, 44 ) c fax-sc o rei luxo da ais lura durante anis 1,5 noras e deixou-se arreleccr durante a noite. Adicionou-se npun (25 οι 1) s&juindo-se a adiçao de acido acético (lou ml) . de colheu-se o solido, lavou-se cor acua e secou-se tara proporcionar acido _/ 2 - ( 4 - c 1 o r o - u e n z i 1 - t i o ) feni 1_/ -acético , t.f. 149-151°C. Aquece u-se ao refluxo durante a noite ur.a solução deste produto (13,3 q) e :.i metanol (2 5 J ml) contendo acido sulfurico concentrado (ϋ,5 ml) e evaporou-se o excesso de metanol . Adicionou-se ater c apua e la vou-se a fase orgânica com hidroxido de sodio aquoso, secou-se e evaporou-se. 0 procíuto solidificado recr istalizou a partir de liexano para proporcionar o estar metil ico do acido cie partida, p. f. 52--54°C. Ϊratou-se este produto com formato de me til o e com hi- - 12
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IXEMPLO 4 O rr .a 'O t lí SC o i c i ο π o lí ~ 3 a cl o 0 1 o o -acetato α e e t i 1 o (22,5 ml) o: v. te t Γα- i: .L ti Γ O L li í.* U i L 0 ^ *j O ...1) , curan to u;;a h o c a , a U: :3 s o 1 u ç a ο a ^ i t a d a c a i .o 1 a a z o ]_ (33,3o G . : Lctra-iii: l r o i. a r a 11 o / a 0 o .al) ;.i a π l!ca a ο' z , a u j ua a l i.i o a α e a Goto. js.iij] s i;;icuu-so a m i s t u r a lí ura ntu .ans uma i ' s ca te a ρ c r c t u r ij . : i i t f o u e a a l c. l a r a a lí r a iiç a u a u-5e o pj reci pitado cor. tetra-a i d r o i- l' C ano . r o c a á a u - s a ... -O, rciesimento pura -o D o u o f i 11 r a a o O d 0 s prosado a .[o 1 co n t o n i c -/ - o :·:o- 1 i midaxol-l-ac eL·; tO 2: a . . o L i i 0 d u u 4 5 ;:i inutos a d isioiiou- s e u... a sol u ç a o de lí L i^oe;!LÍÍ u ipua rd preparado a par t i r d e o - 3 r o :a o — tola a i\o ( ·-; 'a ;/) de i 0 r o :.· o - g t c a o / 3 , / ml) , ^ * 7 / ) a,: l a t a a - a L ã π o , 0!i'pjj.i to se m a n t i a a a a te.: per a lUl a o a tre -Ut e -70 i! o l i ' iui t o u — s c a i; i s t a r a a este t a : \J a .•.tu r a d v. r.uit : 15 t o s o a t e . p o ra tu r a am b i o n t o d a r lí a L c X , 0 i.orac . ug ui d li a a , s acou-sa e a a o são reduzida par t i lo , p.a. v 2-0 7 0 0 n oras uma solução ; e a C o v g r t c u — a c Gρ e 1 o / a 3 a a , g x l r a i u — a a c o o ‘c c r 1 a v a ” e .r. doa extractos com. uca solução salirta,s>
G G :1 t Γ O U — S G . 0 G S t i J. O J — S G G r e S 1 Lt U G SOO proporcionar oxo-(o-tolil)-acetato de /0,5 iam . A l< u e c e u - s e ao refluxo durante deste p r o d u C o (5 ç) sc .cota no 1 ( 1 0 j ..il) coa cio ri d rato do m o - L o x i — a m i n a (2,5o 0 ) . r r a r e c o u — s e a , c i s L ií r a , o v -a u o r ou — s ca , cri- turou-se coo; atar di-isopropilico, £iltrou-sc e cvap o roa- s a o í i 11 r ad o para proporcionar (n: ctoxi-ir,ino)-(o-tolilj-acctuto cg f.isitilo . depois tratou- se com A - b r orno - s uc c i n in i d a gc; tetracloreto de carbono ao refluso sob uma lâmpada de 300 ,,'att, com a d i c a o de peroxido de b e η z o i 1 o (0,005 ç em cada 10 ;r, inutos) .
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0 proces sarnanto convencional proporcionou o composto dc bro-rr.o-setilo que se fez reagir depois com 2 - m. e r c a p t o - b s η z o t i a 2 o 1 oor um processo idêntico no descrito no exemplo 1, para proporcionar ]_ 2-]_ ]_ ( 2-benzo t iazo 1 i 1 ) t i o_/me t i 1_/f era i 1_/( me-toxi-imino)-acetato de metilo, p.f. 113-114°C (Composto 5).
Por um processo idêntico ao descrito em qualquer dos exemplos anteriores, foi possível obter os compostos seguintes :
Salvo quando especificado de outro modo os compostos encontram-se na forma a.
Composto ; g 1 X ^ Íj .u n t; . L b 6-Ct0-benzotiazol-2-ilo S 0 1 100-101 7 benzoxazol-2-ilo s 0 1 01 e 0 b l-Me-imidazol-2-ilo s 0 1 102-104 c. -> 4-ue-pirimidin-2-ilo s 0 1 94-95 10 4,6-Ce9-pirimidin-2-ilo s 0 1 óleo 11 4-iUut-ld-imidazol-2-ilo s 0 1 vidrado 12 (>ieS ) ( 3-me-5-oxo-l-Ph--pirazolin-4-ilidino)metilo 3 0 1 129-131 13 pirimidin-2-ilo S 0 1 7 5-7 õ 14 2-tiazolin-2-ilo s 0 1 105-106 15 5-MeC0-benzotiazol-2-ilo s 0 1 109-110 16 Pn (Isomero Z) s 1 0 92-4 14 -
Urtb/ oniiatlMAL La*...—.......- ê η L · Ο i«l μ> Ο 3 L Ο : ο 17 i-CrQ-ben2Íniidazol-2-ilo 3 3 0 1 o 1 a o Ιο l-Pu-tatrazol-5-ilo 3 3 1 1 2 a - 1 2 7 19 5 - Cl „-ber:zotiazol-2-iio j 4 1 9 7 - v 9 2 U Pu 3 1 0 71-74 214 ,4-ae0-5-;r,et:ilano-2- - t i a z o t i n - 2 - i 1 o 3 3 1 101 22 5-Ph-piri;nidin-2-ilo 3 0 1 10 5 - 1 ú o . 23 6-Cl-4-.:e-benzotiazol-2-ilo 3 J 1 3 J ^ x 9 Λ 5-Oe-benzotiazol-2-ilo 3 0 1 3 3 — 35 25 5 - a η; i η o b e η z i o t i a z o 1 - 2 - i 1 o 3 0 1 -oaa 2 4 - 21 - b e η z o t i a z o 1 - 2 - i 1 o ^J Γι w 1 152-150 27 2 - ρ i r i d i 1 o 3 o 1 0 0-02 2 3 1-(3-.700-?h) tetrazol-5-ilo 3 U 1 05-95 'Ί p, _ y 2-tienilo 3 0 1 54-65 30 5-5e-benzoxazol-2-ilo 3 o f''· u 1 90-91 31 3-Ci.'- 4-COOl t-G-i'ie-2 - p i r i d i 1 o o 0 1 113-114 Ο ° .J 2. 7-Cl-ber. zotiazol-2-ilo 3 0 1 132-134 Ο Ο 5 , o - C 1 - 1 u - b e n z i a. i d a z o 1 - 2 - i 1 o 3 o 1 169 ,5-171 3 3 3-Cl-benzo:;azol-2-ilo 3 0 1 105-107 35 u-Cl-benzotiazol-2-ilo 3 d 1 1 lu-112 3 0 a 5 - 2 - C.. - 2 - 0 a 0.; c - v i a i 1 o 3 o 1 o j vi 3 37 5-(2-li09-bcnzilideno)-4-oxo- -2-tiazolin-2-ilo s u 1 177-175.5 ο >ν· ο 4-0ii-5-..e-o-Pr-piriraidin-2-ilo 3 0 1 77-79 3 9 imidazol_/ 1 ,5-a_/oiridiη-3-i1 o 3 0 1 77-79 40 4-Ph-tiazol-2-ilo 3 0 1 óleo 41 5-propargiltio-l,3,4-tiadia-zol-2-ilo s 0 1 o 1 eo 42 3-C3-4,5-Me0-2-piridilo 3 0 1 140-142 43 3-i.eO-Ph 3 1 0 57-59 44 3-ileO-Ph (isomero Z) 3 1 0 95-9 7 45 l-Pr-benzir?.idazol-2-ilo 3 0 1 5 8 - 7 0 4 ο 4 - D u ^ - P h S 1 0 ólec 47 4-piridilo S 0 1 101-103 4· 3 l-benziltio-2,2-diCN-vinilo S 0 1 97-98
ΒΑϋ UHItàlNAL \__ - 15
UOi.:T;ostO a a Γι1 Π [J . -L . 2 i' / , > l-i.e-5-l.eS-benziraidazol-2-ilo b 6 1 j 5-92 5 0 1-Ph-l,2,4-triazol-3-ilc b 0 1 olao 51 1 - P r1 - b anzÍÍnidazol-2-ilo b 5 1 óleo 5 2 5-Or-benzotiazol-2-ilo b 0 1 124424,. 0 5 5-òr-líi-ben2Íí:'.idazol-2-ilo b u 1 17 9 — 1 o 5 5 4 2 , 2-.·!e2-1 ,3-dioxolan-4-ilo 5 1 0 olao 3· 2,2-i:e.?-l ,3-dioxolan-4-ilo(iso.n.Z) b 1 0 olao 5 6 [39 i il S 2 0 óleo 57 Pn (isómero Z) b 2 o oleo 55 7 -C1 -4-1:2 0- b e nz o t i a z o 1 - 2 - i 1 o S 0 1 loaa 5 9 1:. - b e:: z i r: idazol-2-ilo o U 1 1 6 o — 1 o ú Ο U 5-Cl-benzotiazol-2-ilo b ϋ 1 10 9-11 0 5 1 5 -:: J,, - b α η z o a z o 1 - 2 - i 1 o b 0 1 120-122 o 2 5-t-0u-benzoxazol-2-ilo s u 1 05-o7 ò 5 5-4ts-l-..e-benzimidazol-2-ilo b { 1 V 1 a 6 4 4 , o , 7 - 01- b e η z o t i a z o 1 - 2 - i 1 o b b Ό 1 159-161 o5 5 - P h -1 i a z o 1 - 2 - i 1 o b b 1 ó 1 s o 6o 5 , 7 — '1 a 0 — i) c η z o:: a z o 1 - 2 - i 1 o b b 1 97-90 57 o-Oe-banzoxazol-2-ilo b U i 70-7 3 o c ao r f o 1 i η o t i o x o :.i c t i 1 o b j 1 97-99 69 4-51,3 — *'iοϋ — P11 b 1 J oleo 70 1 ,2,4,-t;riazol-l-ilo b 1 0 oleo 7 1 3 — ugO— ρ i i S 2 ϋ oleo 72 5,7-Clr)-2,3-diidrobenzofuran--2-ilo~ b 1 0 oleo 73 Pn-Cíi=Cíi b 1 0 ó 1 a o 74 1 ,2,4-triazin-3-ilo S 0 1 163 7 5 ρ i r i m i d i π - 4 - i 1 o b ϋ 1 101 76 2 - Me -1 , 3 - d i o o 1 a n - 2 - i 1 o b 1 0 óleo 7 7 ó-Pr-benzotiazol-2-ilo S 0 1 óleo 73 5-Ph0-benzotiazol-2-ilo s 0 1 124-126 7 9 5 - M e C 0 511 - b e η z o t i a z o 1 - 2 - i 1 o s 0 1 151-153 30 4-Ph-Ph s 1 0 131-133 SI n t o-,, A>U = L b 2 0 76-77 co K) Bul-C=C (isómero Z) S 2 0 óleo - 16
BA D ORIGINAL 1
0 4-( i - : i -/lò J - · 1 i. i. X - I I 3 w-. 1 L i X i 1 o I 1 1 o ;> 1 o O - 3 -:· - 0 ::o — o i -· '--i i 11 o o o 1 c i f ' Ί l: 1 a - 2 - i ] o 0· IX . J — 1 ií o 3,, ,.-b 3 II 3 0 t. .1 3 3 0 1 -1 - i lo o ,J : i a j v 7 5-( -a :.i i . O “ 0 ) b e iix 0 <. 1 U X 0 1 — 3 - i i lo 0 t i ]. 0 r, o - 1 X L a a ,) u . A-o X 0 - 3 J ~1' -1 i i à f o cot i n a z o 1 i n - 2 - i 1 o = - i .1 a a 7. 7 χ a i π o 1 i ií — li — i 1 o 0 1 3 o - 0 0 ^ J 3 — .Ί o — X 0 li .3 0 L 1.3301-1(3 - J il i a i π o 2 = 3 1 132 -1 4 1 , 1 ··,- ‘ ! — 1 O i O ) ~~ 1' : 1 1 i s O...0 3 0 ·.) 1 a ia } ; i >— L J 1 . 2 J - 3 [L — 1 1 t — t “ l: x i a x i n - 3 - i 1 o 1 L,7 j - i I o
I 3 o i e o - 1-2 a - 1 , 3 - 1 i o X 0 1 -.1 a - 2 - 110 . > 1 3 0 I x 0 O 2-2 i L — 1 , J“'oÍ0 x 0 1 o 11 - 2 - i 10 ( i s 0.10 0 0 2)2 1 x 120-12 ) a — a 1.3., = .. bon a 0 1 i320 1 -2-i Lo 3 3 ί ^ 0' . A <..* 1 5-2 0,=3:1(..02 ) •1 0 \ , , O lli U A- ( 4-21-20)- t i 3 7.0 1 - 2 - 11 o 0 o 1 0 v — 1 o: 2 0 A “ i 1- ,o-22)- C X a z 0 1 - a - i i 0 x i /3,.: a i i 0 - 0 L - 1 -.. - u o ; i 3 1 i 2. z o 1 - 2 - i J. o ! ; 1 J. J i. ã ~ ..0--:--0 3 0-0 , - a 1 a 1 α c o — 0 a 1 π -a a o - li r. - 2 - i 1 0 - - i i 3 0 -1 X- a 103 Λ- ..e-D-Ou-tiia a 0 1 - 2 - i 1 0 a 3 1 O 10 0 1 34 ·"> : -1 , 4_ 2 e r; z 0 !_ ia a i n — 3 — x 1 o a o 1 0 1 e 0 105 Ί - 1 , - 3 e 11 z 0 a z i π — 3 - i 1 0 2 3 1 0 1 0 0 1 0 0 O - 3 1 - 0 x a z 0 1 oj_ ^ 1 0 - i) / p ί Γ ί d i Π — 2 — 11 0 a U 1 1 14-1 la 1 0 7 0 — 31- i- .o-beo a i a i á a z 01 - 2 - i 1 0 0 1 1 1 -1 > 1 „ — 1 3 j 0 a a ; Γ 0 c 0 s s 0 i a 3 n X i c 0 o. 0 u >' C X ί X 0 li 0 Lj X a .11 t; 1 0 A 0 311 v a x a 1.1- s a 0 s 3 a a, u i Π 10 s C O-.i p 0 S L 0 3 1 17
'trsL
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\.j ) ^ O P: a 0 : i L c a c. o· . . o i i ; i o : i a v a i i λ v o a a a o ff · - - 1 !t C 0 ;.· f ÍJ p 0: 0 L a - - . - 1 t i 1. - 0 i P r o 1 i d o n - . - a 1 raulsioii u - , .. ~ .· o alo o o. a ia .......,,, a e n s - i % .aoiiú:! ooí;tra a ao ti v i cace a o a o l a n x s 0 ) SOOilOJ i ο I x a p s s >. i: " l (1 ..:; L s') c d 1 a s o.o u a r a v i c i c ο I a : ... i 1 ; c o oen r ; s i la: , p a .piais: a Ildeo ...uive d v rica 1 a r i r. o .· /00.. : d a 111 c u 1 a r 1 o s a s a !: i i : f o u u - e.: . o t- P v L L s a i n e r a .u : ί ο lor ciaceut V 0 G X 1 i Γ 1 i p • . .· ; , ; . d a c : 1 a i. a r o 0 G : P 1 t U : ~ · | · ; ' - - , .. s 3 o 1 :0O;)O3t0E , Pi a o o ri c -i n traçuo dose ; ;e c t a n L o , I orao; apli casas oop a. caule das p ia alas c. a ensaio, le c. u .!- a di a a a o a a ^ a i\ ‘c a s o a t o o, e nico s a n t i d a 3 s o li o o n à i c o as c i. dí c n t j o t.' L G ,: , i
X S C I .* X 1 G • C O . . a t 0 Í f O i. X )
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2 v:\ua Í...J o G-vi ) Ç SS O i. ) • 2 - ° L L- i ) 1:ç o c: 3 ou u L s ρ o r s o o s α q u o sa s dos lo, .i. ;i c i u indo uo aente nu-
- P 3 0 O OU ... O j_ :í Ό »U d (J U l» S J S O _s assas oianiias fora.: ino-. o a s a i o a o a o r; r i a . ios a i o r a a _o .i l l ϋ j. 'lis _ia a >j lí au a a \> a i a a ii 0 a o o o a a o v o i v i.. j s u o i a u o - ; a a u . i' o c o p c i ao u a. c u i.í ... o a o c o o c x a a ο ο ο 11. i o u — s a o c a u i. a i a — eccao da suoerficie da folia; oor ur; oro cesso visual. onsidorou-se que os c ο μ ρ o s t o s ara;:; 1V3 s 33 e iiioporcio a a s s e .o u o d e doença para u ;u a c o n : o a t r o 1 o superioi a 5 d d do e s-ítraçao de 12 5 ρ pπ (p/v) ou in terior. 19
r' ο 2 - s e a inoculação de balões contendo alimento de m i 1 η o / a raia c ο m fundos de ensaio e depois f oz--se a incubaçao. As culturas de alimento de ailho/areia forai utilizadas para infestar composto de envasar que se colocou depois em vasos de plástico. Adicionou-se aos vasos solucues ou dispersões aquosas dos compostos, incluindo um agente hu- : o ectante cara proporcio n a r u m a concant r a c ao d e s e i a d a i o s t o eu vaso ! Z - S ; o ajusta m en t o dos vasos de contro- .o por adiçao de soluçoca ou dispe. ; o í lUSllCl: o com posto de ensaio, i.r.edia tam.en te apos a aplicaçao do composto de ensaio semeou-se em cada vaso diversas sementes da couve. A s sementes foram cober tyas com solo infestado tratado e fez--se a incubaçao dos vasos sob condiçoes ambientais controla-uas adequadas para o crescimento das plantas a para o desenvolvimento da doença. i'ez -se a con tapem do numero de rebentos de couve -que nascera::, e calculou-se o controlo :1a doença percentual por compara ç. a o cor. o s vasos i n f e stados a a o t r a t a -dos. : o m p o s t o s era m considerou-se qu: a r; _> 0 /O sobre eu p e s o do c o lur, i ^ do solo . a c t i v o s se efectuassem um controlo superior doença para uma concentração de 100 partes eu peso ao corpos to, ou inferior, por milhão de partes em volume do solo. A demonstração de actividade e a se guinte ( + = activo) 20 bad original Q\
IMPOSTO' No PI PV EG PO PS BC VI RS PR / 1 + + 4- 4- + 4 2 4 3 + 4 4- 4 4 + 4 4 6 + 4· + 4 4 7 + 4- + 4 4 8 4- 9 4 4* + 4 + 10 + + + + + 11 4 12 4 4 13 + 4- 4- + 14 + 4- 4- 4 15 + 4· 4 4 4 4 16 + 4- 4 17 4 + 18 4 19 4 4- 4 4 20 + 4· 4 21 + + 4 4 + 22 + 4- + + + 4- + + 23 + + 4- 4 4 4 + 24 + 4· 4· 4 4 4 4 4 25 + 4· 4- 4 4 4 26 + 4· 4- 4 4 4 27 + 4- 4- 4 4 28 + 4· 4 29 + 4- 4 4 30 4 4- 4- 4 4 4 4 4 31 4- 4· 4 4 32 4 4- 4 4 4
I 21 bad original. kmfc*'— <i
rr\- - π ίΛ . m / ·, υυϊ.ΓυΟ 1 J o PI TJV 1 V ^4 V) X tV .J \7 70 + 71 + 7 3 + + -1· 7 4 .L 75 + *r 7 o + *r + 77 + + «L T 73 + + *r -f 79 -í- O 0 "Γ + 31 -í- T 32 + *r O J + 101 + + a m η 1 o 3 d e ij n s ti i o
Esta exe;;i[;lo ilustra a actividado ia secticiáa dos co.npostos cia presanto invenção. lez-so a aplicaçao de aliquotas de 1 ::il de unia solução em acetona contendo o composto de ensaio em diversas concentrações a rolos de fio dental de ala odao de 1 cr; ; x 2 cm contidos em frascos de vidro c or.i 2 cm ú e d i 3 ia 6 t Γ O por 5 cm de comprim ento. Apos a s e c a g e m fez -se a i π l) γ gnaçao aos materiais trata dos com 1 ml d e uma s oluçao nutri- ente, infestada com larvas de varejeira das ovelhas no primeiro estádio de desenvolvimento (Lucilia sericata), fechados por um bujao de tecido de algodao e mantidos a 25°C durante 24 horas. Para os elementos de controlo a mortalidade foi inferior a 5% ao passo que os compostos dos Exemplos 6, 13, 15, 19, 21-24, 30, 32, 34, 35, 40, 49, 52, Ó0 e 61 apresentaram um valor LC^q para concentrações inferiores a 300 ppm.
BAU OniUtlMAW 23

Claims (1)

  1. χ ν - 1« - ρίΙΓΧ B p l 0 p XI l B ,’ B O u Lr U ' > \ 20 . •j o s t o d e for:.. u 1 a I 1 - ( Cxl „ ) .1. ~ ( L.11 ,· )
    J (I) u;í e ia q u e ou Λ) v: representa CiJ , ea» que ou a) ;q representa hidrogénio , ‘Λ'’ representa hidrogénio ou alquilo, ρ r e ri r e s e n t a 1 e (i) n representa 1, representa 0, X represente S,d, Si;.,, b i (í;R“ ) , 3L(.:“)7 ou Si(GX")„ e representa R'', er. que d"5 representa h e t a r o - a r i 1 o opcionalner.ts sibstituicio , hetero-ciclico opcionalaente substituído, n e t e r o - e i c 1 i 1 ( t i o ) carbonilo (oocionalaente substituído, alquenilo opcionalmen-te substituído, alquinilo opcional;:!ente substituído, X-inino--netileno substituído opcional-,ente substituído, hetero-ci-clilidenoiv.etilo substituído; ou (ii) n representa 0, esta coapreendido entre 1 e lã, X representa S e R1 representa R"3 ou representa arilo opcional mente substituído; ou seis membros hetero-atomos, n estão com- b) Q e R-3 formam parte de um anel de cinco ou que pode ser substituído e pode conter outros especialmente azoto, p representa 0 ou 1, m e BAU uruUiNAL 24
    V
    :ο. [ u ο s t ο r fornato da íoraula sol cunlcílinus a oiicion-iLioati' , se : ·· - tos e.: que representa 30 ou 3J.} , o:: i d a η v. o u:.: a o :q, esto e:s que .. representa 3, e oscionalaente se for:.· ar ue. sal αα qualquer c o i o a o s t o que seja u.·: acido ou u:; α las c . _ a _
    O .UOi. dd ·- C 'y U '«.) i. j w ú t .1 ·» L O 1. i il li O i / O L ; l 1 L 3- ) ^ óe i i j sentar J,, ou .·. , e i.”1 representara., :·:atilo, d o ú* reuresontar hetero-ariio. A requerente declara que os primeiros pedidos desta patente foram apresentados na Gra-Bretanha em 11 de Julho de 1987 e em 29 de Março de 1988, sob os n.cs. 87/16392 e 88/07388, respectivamente. Lisboa, 8 de Julho de 1988 0 AGENTE OFICIAL DA PROPRIEDADE INOUSTRiAv
    Patente Νβ 87938
    RESUMO "PROCESSO PARA A PREPARAÇÃO DE ACRILATOS COM ACTIVIDADE FUNGICIDA" A invenção refere-se a uni processo para a preparaçao de ura composto de fórmula I .‘-to.,)
    (i: e dos sais de adiçao de ácido de quais quer compostos que sejam alcalinos e sais de adição de base de quaisquer compostos que sejam ácidos, que compreende fazer-se reagir um composto de fórmula II
    em que 2 representa um grupo removível tal como halogéneo. com um composto de fórmula III b1<cii2VVh (iii) ou, quando W representar CH, fazer reagir um composto de fórmula IV (IV)
    com um éster formato da fórmula V HCOOR2 (V) sob condlçoes alcalinas, e opcionalmente, se obterem compostos em que X representa SO ou SO^, oxidando um composto em que X representa S, e, opcionalmente se formar um sal de qualquer composto que seja um ácido ou una base.
PT87938A 1987-07-11 1988-07-08 Processo para a preparacao de acrilatos com actividade fungicida PT87938B (pt)

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GB878716392A GB8716392D0 (en) 1987-07-11 1987-07-11 Fungicides
GB888807388A GB8807388D0 (en) 1988-03-29 1988-03-29 Fungicides

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PT87938B true PT87938B (pt) 1995-03-01

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US5304530A (en) 1994-04-19
YU131888A (en) 1990-12-31
ZW9388A1 (en) 1989-02-01
HUT47373A (en) 1989-03-28
EP0299694B1 (en) 2000-10-11
PT87938A (pt) 1989-06-30
JPS6431746A (en) 1989-02-02
IL87020A (en) 1996-09-12
NZ225339A (en) 1990-05-28
JP2688495B2 (ja) 1997-12-10
US5192357A (en) 1993-03-09
CN1031227A (zh) 1989-02-22
KR960012207B1 (ko) 1996-09-16
DK381588D0 (da) 1988-07-08
DE3856431D1 (de) 2000-11-16
EP0299694A2 (en) 1989-01-18
YU47288B (sh) 1995-01-31
CN1025649C (zh) 1994-08-17
KR890002091A (ko) 1989-04-08
BR8803436A (pt) 1989-01-24
AU1880688A (en) 1989-01-12
EP0299694A3 (en) 1989-11-29
FI883297A0 (fi) 1988-07-11
DK381588A (da) 1989-01-12
TR24201A (tr) 1991-07-01
ATE196900T1 (de) 2000-10-15
HU204658B (en) 1992-02-28
FI92392C (fi) 1994-11-10
FI883297L (fi) 1989-01-12
DE3856431T2 (de) 2001-02-08
IL87020A0 (en) 1988-12-30
AU607235B2 (en) 1991-02-28
FI92392B (fi) 1994-07-29

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