FI70577B - N- (HETEROCYCLISK-AMINOCARBONYL) -ARYL SULPHONAMIDER ANVAENDBARA SOM HERBICIDER OCH VAEXTERNAS TILLVAEXTREGULERANDE AEMNEN - Google Patents
N- (HETEROCYCLISK-AMINOCARBONYL) -ARYL SULPHONAMIDER ANVAENDBARA SOM HERBICIDER OCH VAEXTERNAS TILLVAEXTREGULERANDE AEMNEN Download PDFInfo
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- FI70577B FI70577B FI771123A FI771123A FI70577B FI 70577 B FI70577 B FI 70577B FI 771123 A FI771123 A FI 771123A FI 771123 A FI771123 A FI 771123A FI 70577 B FI70577 B FI 70577B
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- hydrogen
- methyl
- chlorine
- aminocarbonyl
- fluorine
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- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
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- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
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- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Description
ΓΒ1 ^KUULUTUSJULKAISU ππς^π LBJ (11) utlägg ni ngsskrift /Uo / ( c (45) f:··1 b 1 ·-a-vlty ^ ^ ^ (51) Kv.ik.*/lnt.ci.* c 07 D 239/^2, 251/1*4 , *405/ 1 2 , ' ' *409/12, A 01 N *43/5*4 , *43/66 SUO M I —Fl N L AN D (21) Patenttihakemus - Patontansökning 771123 (22) Hakemispäivä — Ansökningsdag n-i «r __ /ci\ /,UM·7* V / (23) Alkupäivä —Giltighetsdag g^ g^ (41) Tullut julkiseksi — Blivit offentlig gg ^ΓΒ1 ^ ADVERTISEMENT PUBLICATION ππς ^ π LBJ (11) utlägg ni ngsskrift / Uo / (c (45) f: ·· 1 b 1 · -a-vlty ^ ^ ^ (51) Kv.ik. * / Lnt.ci. * c 07 D 239 / ^ 2, 251/1 * 4, * 405/1 2, '' * 409/12, A 01 N * 43/5 * 4, * 43/66 SUO MI —Fl NL AN D (21 ) Patent application - Patontansökning 771123 (22) Date of application - Ansökningsdag ni «r __ / ci \ /, UM · 7 * V / (23) Starting date —Giltighetsdag g ^ g ^ (41) Published public - Blivit offentlig gg ^
Patentti- ja rekisterihallitus Nähtäväksipanon ja kuul.julkaisun pvm.— . -National Board of Patents and Registration Date of display and publication—. -
Patent- och registerstyrelsen ' ' Ansökan utlagd och utl.skriften publicerad Uo.0b.o6 (86) Kv. hakemus — Int. ansökan (32)(33)(31) Pyydetty etuoikeus — Begärd prioritet 07.0*4.76 23.02.77, 23.02.77 USA(US) 67*t668, 769913 76991** ’ (71) E.l. du Pont de Nemours and Company, Wilmington, Delaware 19898, USA(US) (72) George Levitt, Wilmington, Delaware, USA(US) (7*4) Oy Kolster Ab (5*4) Herbisideinä ja kasvien kasvunsäätäj i;.ä käytettävät N-(heterosykl inen-aminokarbonyy1i)aryylisu 1fonamidit - N-(heterocyklisk-aminokarbony1)-arylsulfonamider användbara som herbicider och växternas ti11växtregu-lerande ämnenPatent and registration authorities '' Ansökan utlagd och utl.skriften publicerad Uo.0b.o6 (86) Kv. application - Int. trap (32) (33) (31) Claim claimed - Begärd priority 07.0 * 4.76 23.02.77, 23.02.77 USA 67 * t668, 769913 76991 ** '(71) E.l. du Pont de Nemours and Company, Wilmington, Delaware 19898, USA (72) George Levitt, Wilmington, Delaware, USA (7 * 4) Oy Kolster Ab (5 * 4) As herbicides and plant growth regulator i ;. N- (heterocyclic aminocarbonyl) arylsulfonamides to be used - N- (heterocyclic aminocarbonyl) -arylsulfonamides and other herbicides and other tertiary esters
Keksinnön kohteena ovat maanviljelvssä käytciTvät N-(heterosvk-1 inen-amin o k a r b o n y y 1 L ) -aryyl isulf on lam 1 rl i t.The invention relates to N- (heteroskk-1 inen-Amin o k a r b o n y y 1 L) -aryl isulfone lam 1 rl i t for use in agriculture.
Ranskalaisessa pat ent issa no. 1 !l 6H 71 / esitetään naaraavat pa-ra-substi tuo lelut fenyyl isulfon ianid.it , jotka ovat kayttökelpo isi a an- tidiabeett isinä aineina ( sokeritaut i lääkke inä ) : _ 0 h—// \\—3 C- MI ϊ - C - NH - jotta R on H, halogeeni, CT tai nlkyylL.In French pat ent no. 1 6H 71 / discloses female para-substituents which are phenylsulfone ianides which are useful as antidiabetic agents (as medicaments for diabetes): _ 0 h - // \\ - 3 C- MI ϊ - C - NH - so that R is H, halogen, CT or alkyl.
Loyernann et. ai . , Tuon. Aio , tl, 1H ij 6 7 p ( 1 k k 9 ) , esittävät joukon sulfeniam iuJe-ί a , jotka kas ittävMi u mm i. i 1 i-j ohdanna 1 s ia sekä yhdisteitä , joilla on naava:Loyernann et. ai. , That. Aio, tl, 1H ij 6 7 p (1 k k 9), show a series of sulfeniam iuJe-ί a which are used, e.g., i 1 i-j derivative 1 s ia and compounds having the naava:
H 30.NHCNHRH 30.NHCNHR
jossa R on butyy1i, fenyyl ί tai (\ \ ]a R. en vety ta i metyyli.wherein R is butyl, phenyl or (\ r) a R. en hydrogen or methyl.
Rl 70577Rl 70577
Testattaessa näitä yhdisteitä vaikutuksensa suhteen verensokeriniuk-kuuteen rotilla (annokset 2b mg/100 g suun kautta) olivat yhdisteet, joissa R on butyyli ja fenyyli, kaikkein tehokkaimmat. Muut olivat vähätehoisia tai inaktiivisia.When tested for their effect on hypoglycemia in rats (doses of 2b mg / 100 g orally), compounds in which R is butyl and phenyl were the most effective. Others were ineffective or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, s. 121-5 (1962) /Chem. Av., 59 1633 e.7 kuvaa N-Z~( 2 , B-dime toksipyrimidin-4-yyli ) aminokarbonyyli_7-1*-metyylibentseenisulfonamidin synteesiä: OCHaWojciechowski, J. Acta. Polo. Pharm. 19, pp. 121-5 (1962) / Chem. Av., 59 1633 e.7 describes the synthesis of N-Z- (2,2-dimethoxypyrimidin-4-yl) aminocarbonyl_7-1 * -methylbenzenesulfonamide: OCHa
Perustuen samankaltaisuuteen erään tunnetun yhdisteen kanssa, tekijä ennusti esitetyllä yhdisteellä olevan vaikutusta verensokeri-niukkuuteen.Based on similarity to a known compound, the factor predicted the effect of the disclosed compound on blood glucose deficiency.
Hollantilainen patentti 121.788, julkaistu 15.9.1966, opettaa kaavan (i) yhdisteiden valmistamisen ja niiden käytön yleisinä tai selektiivisinä rikkaruohomyrkkyinä, /qVsq.hhcii-0 (i) in7 ItHKlDutch patent 121,788, published September 15, 1966, teaches the preparation of compounds of formula (i) and their use as general or selective herbicides, /qVsq.hhcii-0 (i) in7 ItHKl
Ha jossa R^ ja R^ voivat toisistaan riippumatta olla 1-4 hiiliatomia sisältävä alkyyli; ja R^ ja R^ voivat toisistaan riippumatta olla vety, kloori tai alkyyli, jossa on I-4 hiiliatomia.Ha wherein R 1 and R 2 may independently be alkyl of 1 to 4 carbon atoms; and R 1 and R 2 may independently be hydrogen, chlorine or alkyl of 1 to 4 carbon atoms.
Yhdisteitä, joilla on kaava (ii), ja niiden käyttöä antidia-beettisina aineina, on selostettu julkaisussa J. Drug Res. 6, 123 (1974) .The compounds of formula (ii) and their use as antidiabetic agents are described in J. Drug Res. 6, 123 (1974).
ö\ " (11)ö \ "(11)
SOaNHCNHRSOaNHCNHR
11 3 70577 jossa R on pyridyyli.11 3 70577 wherein R is pyridyl.
Ei toivotun kasvi.il i s nude n läsnäolo aiheuttaa oleellista vahinkoa hyödyllisille kasveille, erityisesti maanviljelystuotteille , jotka tyydyttävät ihmisen perusruuan ja kuitujen tarpeen, kuten puuvilla, riisi, maissi, vehnä, soijapapu jne. Nykyisin räjähdysmäinen väestönkasvu ja maai Iinan samanaikainen ruoka-aine- ja kuitu-pula vaativat parannuksia näiden kasv.i en tuotantotehokkuuteen. Osan tällaisista arvokkaista kasveista hukkaanmenon estämiseksi tai vähentämiseksi tappamalla tai estämällä ei toivotun kasvillisuuden kasvu on eräs tapa parantaa tätä tehokkuutta.The presence of an unwanted plant.il is nude n causes substantial damage to beneficial plants, especially agricultural products that meet the needs of human staple food and fiber such as cotton, rice, corn, wheat, soybeans, etc. fiber shortages require improvements in the production efficiency of these growths. To prevent or reduce the loss of some of such valuable plants by killing or inhibiting the growth of unwanted vegetation is one way to improve this efficiency.
Käytettävissä on suuri joukko aineita, jotka ovat käyttökelpoisia tappamaan tai estämään (torjumaan) ei-toivotun kasvillisuuden kasvua-, tällaisia aineita nimitetään yleisesti herbisideiksi. Kuitenkin on olemassa tarve löytää vielä tehokkaampia herbisidejä, jotka hävittävät tai torjuvat rikkaruohoja aiheuttamatta merkittävää vahinkoa hyödyllisille kasveille. Eräät rikkaruohot (esimerkkinä erityisesti pähkinäsara) ovat hyvin vaikeat hillitä; monet rikkaruo-homyrkyistä, joita käytetään torjumaan pähkinäsaraa ovat niin ei-selektiivisiä, että ne aiheuttavat vahinkoa itse kasveille.There are a wide variety of agents available that are useful for killing or preventing (combating) the growth of unwanted vegetation, such agents are commonly referred to as herbicides. However, there is a need to find even more effective herbicides that eradicate or control weeds without causing significant damage to beneficial plants. Some weeds (especially the nutcracker in particular) are very difficult to control; Many of the herbicides used to control nutcrackers are so non-selective that they cause damage to the plants themselves.
Tämän keksinnön mukaisesti tarjotaan uusia kaavan I yhdisteitä sekä niiden maanviljelyksellisesti sopivia suoloja, sopivia maanvi1je lysyhdistelmiä, jotka sisältävät niitä sekä menetelmiä niiden käyttämiseksi selektiivisinä sekä myös yleisinä rikkaruoho-myrkkyinä, jotka ovat vaikuttavia sekä ennen ilmaantumista että sen jälkeen. Nämä yhdisteet ovat erittäin tehokkaita rikkaruohomyrkkyjä. Ne ovat erityisen käyttökelpoisia torjuttaessa pähkinäsaraa ja niiden aiheuttama vahinko halutuille kasveille, kuten puuvillalle, riisille, maissille, vehnälle jne. on häviävän pieni.According to the present invention there are provided novel compounds of formula I and their agriculturally acceptable salts, suitable agricultural combinations containing them and methods for their use as selective as well as common herbicides which are effective both before and after emergence. These compounds are very effective herbicides. They are particularly useful in controlling nutcrackers and the damage they cause to desired crops such as cotton, rice, corn, wheat, etc. is negligible.
WW
R1-S02-NH-C-NII-R I.R1-SO2-NH-C-NII-R I.
jossa R on : N / tai N —Swherein R is: N / or N -S
O, Q 1 on H3 R4O, Q 1 is H 3 R 4
K'· *3 /3 ifrSK '· * 3/3 ifrS
PY \ % Hg R10 „ 70577PY \% Hg R10 „70577
Rg on vety, fluori, kloori, bromi, jodi, C^-C^-alkyyli, C^-C -alkoksi, nitro, trifluorimetyyli , syaani, CH,,S(0) - tai CH~CH„S tai CH3CH2S02; R^ on vety, fluori, kloori, nitro tai metyyli;R 9 is hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano, CH 2 S (O) - or CH 2 CH 2 S or CH 3 CH 2 SO 2; R 1 is hydrogen, fluorine, chlorine, nitro or methyl;
Rg on vety, fluori, kloori, metyyli tai metoksi;Rg is hydrogen, fluorine, chlorine, methyl or methoxy;
Rg on vety, fluori, kloori, bromi, C^-C^-alkyyli, C^-C^-alkoksi, nitro, trifluorimetyyli, syaani tai CHgSCO)^; R7 on vety, fluori, kloori, C^-C^-alkyyli tai C^-C^-alkoksi,R 9 is hydrogen, fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano or CH 2 SO 2); R 7 is hydrogen, fluorine, chlorine, C 1 -C 4 alkyl or C 1 -C 4 alkoxy,
Rg on vety, metyyli tai kloori;Rg is hydrogen, methyl or chlorine;
Rg on vety, kloori tai bromi; R^g on vety, kloori, bromi tai metyyli; W ja Q ovat toisistaan riippumatta happi tai rikki; n on 0, 1 tai 2 ; X on vety, kloori, bromi, metyyli, etyyli, alkoksi, jossa on 1-3 hiiliatomia, trifluorimetyyli, CHgS- tai CHgOCHg-; ja Z on metyyli tai metoksi; tai niiden maanviljelyksellisesti sopivat suolat; edellyttäen, että a) kun Rg on muu kuin vety, on ainakin joku ryhmistä Rg , R^ , Rg ja Ry muu kuin vety ja ainakin kaksi ryhmistä Rg , , Rg ja R? on vety; b) kun Rg on vety ja yksikään ryhmistä Rg , R^, Rg ja R? ei ole vety, niin täytyy kaikkien ryhmien R , R^, Rg ja R? olla joko kloori tai metyyli; ja c) kun Rg ja R? ovat kumpikin vety, täytyy ainakin yhden ryhmistä R^, Rg tai Rg olla vety.Rg is hydrogen, chlorine or bromine; R 1g is hydrogen, chlorine, bromine or methyl; W and Q are independently oxygen or sulfur; n is 0, 1 or 2; X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1 to 3 carbon atoms, trifluoromethyl, CH 2 S 5 or CH 2 OCH 6 -; and Z is methyl or methoxy; or their agriculturally acceptable salts; provided that a) when Rg is other than hydrogen, at least one of Rg, R1, Rg and Ry is other than hydrogen and at least two of Rg, Rg and R? is hydrogen; b) when Rg is hydrogen and none of Rg, R1, R8 and R8? is not hydrogen, so must all the groups R, R ^, Rg and R? be either chlorine or methyl; and c) when Rg and R? are each hydrogen, at least one of R 1, R 8 or R 8 must be hydrogen.
Edullisia lisääntyvässä suosituimmuusjärjestyksessä, perustuen tehokkuuteen tai hintaan tai molempiin, ovat 1) ne yhdisteet, joilla on edellä määritelty kaava I, jossa R^ on V <- r\R .Preferred in ascending order of preference, based on efficacy or cost, or both, are 1) those compounds of formula I as defined above, wherein R 1 is V <- r \ R.
R.7 R6 2) suosituimmuuden 1) yhdisteet, joissa Rg on vety, fluori, kloori, bromi, 1-4 hiiliatomia sisältävä alkyyli, alkoksi, jossa on 1-4 hiiliatomia, CHgS- tai CHgCHgS-; ja R, on vety, fluori, kloori, bromi, lai mcrl.yyli; jaR.7 R6 2) compounds of most preferred 1) wherein Rg is hydrogen, fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, CH2S- or CH2CH2S-; and R 1 is hydrogen, fluorine, chlorine, bromine, laxyl; and
Rg on vety, fluori, kloori, bromi, alkyyli, jossa on 1-4 70577 hiiliatomia, alkoksi, jossa on ]-4 h i i 1 La l omia , triiluorimotyy1i, nitro, CH^S- tai CII^CH^S-; e del 1 y t Laon , että: а) kun on muu kuin vety, täytyy ryhmien R^, R^ , R tai ri i ppuma4: tomas t i olla vety, fluori, kloori, bromi, metyyli tai metoksi; 3) suosituimmuuden 2 yhdisteet, joissa (a) R on pyrididinyyliradikaali; X on metyyli tai alkoksi, jossa on 1-3 hiiliatomia; ja Z on metyyli tai metoksi; tai (b) R on triatsinyyliradikaali; X on metyyli tai alkoksi, jossa on 1-3 hiiliatomia; ja Z on metoksi; 4) suosituimmuuden 3) yhdisteet, joissa on vety, fluori, kloori, bromi, alkyyli, jossa on 1-2 hiiliatomia, alkoksi, jossa on 1-2 hiiliatomia, CH^S- tai CH^CH^S-; ja R^ , R^ ja R.-, ovat riippumattomasti vety, fluori, kloori tai metyyli; jaR 9 is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4,70577 carbon atoms, alkoxy of 1 -4 h 1 1 L 1 O, trifluoromotyl, nitro, CH 2 S- or Cl 2 CH 2 S-; e del 1 y t Laon that: а) when it is other than hydrogen, the groups R 1, R 2, R 1 or R 1 must be hydrogen, fluorine, chlorine, bromine, methyl or methoxy; 3) compounds of Most Preferred 2 wherein (a) R is a pyridinidinyl radical; X is methyl or alkoxy of 1 to 3 carbon atoms; and Z is methyl or methoxy; or (b) R is a triazinyl radical; X is methyl or alkoxy of 1 to 3 carbon atoms; and Z is methoxy; 4) most preferred 3) compounds having hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms, alkoxy of 1-2 carbon atoms, CH 2 S- or CH 2 CH 2 S-; and R 1, R 2 and R 4 are independently hydrogen, fluorine, chlorine or methyl; and
Rg on vety, fluori., kloori, bromi, alkyyli, jossa on 1-2 hiiliatomia, alkoksi, jossa on 1-2 hiiliatomia, trifluorimetyy-li, nitro, CH^S- tai CH^CH^S-; 3) suosituimmuuden 3) yhdisteet, joissa R^ , R^ , R<- , Rg ja R^ ovat riippumattomasti vety, fluori, kloori tai metyyli; б) suosituimmuuden 3) yhdisteet, joissa R^ on fluori, kloori, tai metyyli; ja R^ , Rg, R^. ja ovat riippumattomasti vety, fluori, kloori tai metyyli; edellyttäen, että: kun Rg on muu kuin vety, täytyy R^m ja Rg: n olla vety; 7) suosituimmuuden 3) yhdisteet, joissa R^ on fluori, kloori tai metyyli; ja R^ ja Rg ovat vety; jaR 9 is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms, trifluoromethyl, nitro, CH 2 S or CH 2 CH 2 S; 3) most preferred 3) compounds wherein R 1, R 2, R 6 -, R 8 and R 2 are independently hydrogen, fluorine, chlorine or methyl; б) most preferred 3) compounds wherein R 1 is fluoro, chloro, or methyl; and R 1, R 8, R 2. and are independently hydrogen, fluorine, chlorine or methyl; provided that: when R g is other than hydrogen, R m and R g must be hydrogen; 7) most preferred 3) compounds wherein R 1 is fluoro, chloro or methyl; and R 1 and R 8 are hydrogen; and
Rg ja R? ovat toisistaan riippumatta vety, fluori, kloori tai metyyli; 8) suosituimmuuden 3) yhdisteet, joissa R^ on vety, fluori, kloori, bromi, alkyyli, jossa on 1-4 hiiliatomia, alkoksi, jossa on 1-4 hiiliatomia, CH^S- tai CH^CH^S-; ja R^, Rg ja R.j ovat vety; jaRg and R? are independently hydrogen, fluorine, chlorine or methyl; 8) most preferred 3) compounds wherein R 1 is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, CH 2 S or CH 2 CH 2 S-; and R 1, R 8 and R 4 are hydrogen; and
Rg on vety, fluori, kloori, bromi, alkyyli, jossa on 1-4 hiiliatomia, alkoksi, jossa on 1-4 hiiliatomia, trifluorimetyyli, nitro, CHgS- tai CH^CH^S; 9) suosituimmuuden 8) yhdisteet, joissa R^ on fluori, kloori, bromi, alkyyli, jossa on 1-2 hiiliatomia tai alkoksi, jossa on 1-2 6 70577 hiiliatomia; jaR 9 is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, nitro, CH 2 S or CH 2 CH 2 S; 9) most preferred 8) compounds wherein R 1 is fluoro, chloro, bromo, alkyl of 1-2 carbon atoms or alkoxy of 1-2 6 70577 carbon atoms; and
Rp. on vety, fluori, kloori., brorni, ulkyyli, jossa on 1-2 hiiliatomia, alkoksi, jossa on 1-2 hiiliatomia, trifluorimetyyli tai nitro; ja 10) suosituimmuuden 8) yhdisteet, joissa on fluori, kloori, bromi, metyyli tai metoksi; jaRp. is hydrogen, fluorine, chlorine, bromine, alkyl having 1-2 carbon atoms, alkoxy having 1-2 carbon atoms, trifluoromethyl or nitro; and 10) most preferred 8) compounds having fluorine, chlorine, bromine, methyl or methoxy; and
Rj. on vety, fluori, kloori, bromi, metyyli, metoksi tai ni t ro.Rj. is hydrogen, fluorine, chlorine, bromine, methyl, methoxy or nitro.
Edullisia ovat myös lisääntyvässä suosituimmuusjärjestyksessä, joka perustuu tehokkuuteen tai hintaan tai kumpaankin: A) ne edellä määritellyt kaavan I yhdisteet, joissa R on:Also preferred in ascending order of preference based on efficacy or cost, or both: A) those compounds of formula I as defined above wherein R is:
jr\ tai jtLjr \ or jtL
B) suosutuimmuuden A) yhdisteet, joissa (a) R on pyrimidinyy-liradikaali; Q on rikki; X on metyyli tai alkoksi, jossa on 1-3 hiiliatomia; ja X on metyyli tai metoksi; ja R on triat sinyy1i-radikaali; Q on rikki; X on metyyli tai alkoksi, jossa on 1-3 hiiliatomia; ja Z on metoksi; C) suosituimmuuden A) yhdisteet, joissa:B) most preferred compounds of A) wherein (a) R is a pyrimidinyl radical; Q is broken; X is methyl or alkoxy of 1 to 3 carbon atoms; and X is methyl or methoxy; and R is a triateyl radical; Q is broken; X is methyl or alkoxy of 1 to 3 carbon atoms; and Z is methoxy; C) most popular A) compounds in which:
Rj_ on Π Λ ja Rg on vety.Rj_ is Π Λ and Rg is hydrogen.
Rq'Ns ARq'Ns A
Samalla tavalla ovat tehokkuuden perusteella edullisia ne edellä määritellyn kaavan I yhdisteet, joissa: R-^ on ^ °nSimilarly, on the basis of efficacy, those compounds of formula I as defined above are preferred in which: R 1 is
Erityisen edullisia siLmäänpistävän tehokkuutensa ja erittäin edullisen hintansa tai kummankin perusteella ovat:Particularly advantageous in terms of their striking efficiency and very low price or both are:
IIII
V 70577 1) N - 7( 4 - me t o k s i - 8 - m e t y y 1 ipyrimi cJ i n-2-yyl i )aini nokarbonyyl i 7- 2-klooribentseenisulfoni.amidi , sp. 194-196°C; 2 ) N —Z~( 4 , 6-dimetoksipyrimidin-2-yyli ) aminokarbonyyli7-2 ,5-di- klooribentseenisulfoniamidi, sp. 189-190°C·, 3 ) N-7( 4-metoksi-6-metyylipyrimidin-2-yyli ) aminokarbonyyli7-2- rnetyy 1 i ben tseenis ulf oniamid i , sp. 17?-174°C; ja 4 ) M - 7( 4 ,6-di metyyli pyri midin-2-y yli ) aminokarbonyy.1 i7~2-tio- feenisulfoniamidi, sp. 224-228°C.V 70577 1) N-7 (4-methyl-8-methylpyrimino-2-yl) Ninocarbonyl-2-chlorobenzenesulfonylamide, m.p. 194-196 ° C; 2) N- [2- (4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C ·, 3) N-7- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-methylbenzene Ulfonamide, m.p. ? 17 -174 ° C; and 4) M-7- (4,6-dimethylpyridin-2-yl) aminocarbonyl-17-2-thiophenesulfonamide, m.p. 224-228 ° C.
5) N-7(4-metoksi-6-metyyli-l,3, 5- tri at s in- 2-yy 1 i ) aminokarbonyy-li7“2-klooribentseenisulfoniamid.i, sp. 174-17 8°C; 6) N-ZX4,6-dimetoksi-1,3,5-triatsin-2-yyli)aminokarbonyyli7~2-klooribentseenisulfoniamidi, sp. 188-189°C; ja 7) N-7(4,6-dimetoksi-1,3,5-triats in-2-yyli)aminokarbonyyli7-2,5-dimetoksibentseenisulfoniamidi, sp. 187-188°C.5) N-7- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl-1,2-chlorobenzenesulfonamide, m.p. 174-17 ° C; 6) N-ZX4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl-2-chlorobenzenesulfonamide, m.p. 188-189 ° C; and 7) N-7- (4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2,5-dimethoxybenzenesulfonamide, m.p. 187-188 ° C.
Samalla kun kaikki kaavan I yhdisteet ovat rikkaruohoja hävittäviä, eivät kaikki niistä ole selektiivisiä kaikkien kasvien suhteen. Kuitenkin valikoimalla nimenomaisia yhdisteitä, päästään rikkaruohon torjuntaan ja kasvin turvallisuuteen. Niinpä jotkut yhdisteet ovat erityisen selektiivisiä rikkaruohojen torjunnnan suhteen vehnässä ja riisissä; pähkinäsaran torjuntaan sellaisissa kasveissa, kuin maissi, puuvilla, soijapapu tai riisivesakkojen torjunnassa; ja vesihyasintin torjunnassa. Lisäksi kaavan I yhdisteet ovat hyödyllisiä kasvin kasvun säätelijöitä, esim. lisäten sokeripitoisuutta sokeriruo'ossa ja hirssissä ja tukauttaen siemen-päiden muodostumisen ruohoissa, kuten Bahia-ruohossa.While all of the compounds of formula I are herbicides, not all of them are selective for all plants. However, by selecting specific compounds, weed control and plant safety are achieved. Thus, some compounds are particularly selective for weed control in wheat and rice; to control nutcrack in plants such as maize, cotton, soybeans or rice cakes; and combating water hyacinth. In addition, the compounds of formula I are useful plant growth regulators, e.g. by increasing the sugar content in sugar cane and millet and by suppressing the formation of seed heads in grasses such as Bahia grass.
Erityisen edullisia A) rikkaruohojen selektiiviseen torjuntaan vehnässä ovat: 1) N-7(4-metoksi-6-metyylipyrimidin-2-yyli)aminokarbonyyli7-2-kloori-5-metoksibentseenisulfoniamidi, sp. 199-200°C; 2) N-/X 4-metoks i-6-metyyli-1,3,5-triäts in-2-yyli)aminokarbo-nyyli7-2-klooribentseenisulfoniamidi, sp. 174-178°C; 3 ) N - Z"( 4,6-di met oksi-1,3 , 5-triatsin-2-yy li ) aminokarbonyy 1 i7 - 2- klooribentseenisulfoniamidi, sp. 188-189°C; ja 4) N-Z(4,6-dimetoksi-l,3,5-trials in-2-yyli)ami nokarbonyyli7-2,5- dimetok.s ibontoeen i sulf on iamidi , sp. .187-1 8 8°C .Particularly preferred A) for the selective control of weeds in wheat are: 1) N-7- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl-2-chloro-5-methoxybenzenesulfonamide, m.p. 199-200 ° C; 2) N- (X 4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C; 3) N - Z "(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-2-chlorobenzenesulfonamide, m.p. 188-189 ° C; and 4) NZ (4 (6-dimethoxy-1,3,5-trialsin-2-yl) aminocarbonyl] -2,5-dimethoxy-ibontoene sulfone is mp 187-18 ° C.
β 70577 β) pähkinäsaran selektiiviseen torjuntaan kasveissa ovat: 1) Ν-Λ4,b-di metoks ipyri mi di n-2-yy1i)aminokarbonyy117-2,5- di kloori ben tsuen isu] f on i ami d i. , sp. 189-190°0· ja 2 ) N-/"( 4 , 6-di me tyyli pyridin-2-yyli) aminokarbonyyli7-2 , 6-dikloo- ribentseenisulfoniamidi, sp. 177-182°C; C) vesihyasintin torjuntaan ovat: 1) Ν-Γ( 4-mc-toki; i - Π-me tyyli pyrimi din-2-yyl i ) ami nokarbonyy li7-2-klooribentsecnisulfoniamidi, sp. 194-196°C; 2) d-/~( 4- mu t oks i - 6 - me tyy li-1 , 3 ,5-triatsin-2-yyli) ami nokarbonyy-li7-2-klooribentseenisulfoniamidi, sp. 174-178°C; 3 ) i'l- Z"( 4 , B - d ime t oks i -1, 3 , 9-1. ri at s in - 2 - yy 1 i ) ami nokarbonyy 1 i] - bentseenisuifoniamidi , sp. 18 3-185°C; ja 4 ) N - /f( 4-me toksi-6-metyyli-l, 3 , 5-triatsin-2-yyli) aminokarbonyy- li/-2-kloori-3-metoksibentseenisulfoniamidi, sp. 175-176°C*, D) kasvun säätelyaineiksi ovat: 1) N- Zi( 4 ,6-dimetyylipyrimidin-2-yyli) aminokarbonyyli7 -bentseeni suifoniamidi:, sp. 228-230°C; ja 2 ) N-ZX 4 , 6-dime Loks i pyramid in - 2 -yyl i ) ami nokarbonyy 1 i_7 - 2 , 5-di- klooribentseenisuifoniamidi , sp. 189-190°C.β 70577 β) for the selective control of nut crust in plants are: 1) Ν-Λ4, b-dimethoxy ipyrrine di n-2-yy1i) aminocarbonyl117-2,5-di chloro ben Tsuen isu] f is i ami d i., sp . 189-190 ° C · and 2) N - [(4,6-dimethylpyridin-2-yl) aminocarbonyl] -2,6-dichlorobenzenesulfonamide, m.p. 177-182 ° C; C) for the control of water hyacinth are : 1) Ν-Γ (4-mc-thiol; i - Π-methyl pyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, mp 194-196 ° C; 2) d- / ~ ( 4- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, mp 174-178 ° C; (4, B - d ime toks i -1, 3, 9-1. Ri at s in - 2 - yy 1 i) aminocarbonyl 1 i] - benzenesulfonamide, m.p. 18 3-185 ° C; and 4) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chloro-3-methoxybenzenesulfonamide, m.p. 175-176 ° C *, D) growth regulators are: 1) N-Z 1 (4,6-dimethylpyrimidin-2-yl) aminocarbonyl-7-benzene sulfonamide: m.p. 228-230 ° C; and 2) N-ZX 4,6-dimethoxy-pyramidin-2-yl) aminocarbonyl-7- to 2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C.
3 ) N - 7 ( 4 ,b-d i me toks i - i ,3 , b-triatsin-2-yyli ) am i nokarbonyy 1 i7 - bentseenisulfoniainidi , sp. 183-185°C; 4) N-7(4-me tokc i-b-me tyy1i-1,3 ,5-triatsi. n-2-yyli) ami nokarbonyy-li7-bentseeni sulfon laini di ·, 5) N - 7( 4,6-di me tyy li-1 ,3 , 8-triatsin-2-yyli)aminokarbonyyli7 -bentseenisuifoniamidi, sp. 200-201°C; ja δ) U-/(4-metoksi-6-metyyli-1,3,5-triatsin-2-yyli)aminokarbo- nyyli7-2-klooribentseenisulfoniamidi, sp. 174-178°C.3) N - 7 (4, b-dimethoxy-1,3,3-triazin-2-yl) aminocarbonyl-17-benzenesulfonamide, m.p. 183-185 ° C; 4) N-7 (4-methoxy-methyl-1,3,5-triazin-2-yl) aminocarbonyl-7-benzene sulfone Laini di ·, 5) N - 7 (4,6- dimethyl-1,3,8-triazin-2-yl) aminocarbonyl-7-benzenesulfonamide, m.p. 200-201 ° C and δ) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C.
E) rikkaruohojen selektiiviseen torjuntaan riisissä ovat: 1) N - /"( 4-me tyy 1 ipyrimidin -2- yy 1 i ) aminokarbonyyli_7-2-kloori-bentseenisulfoniamidi , sp. 201-203°C; ja 2) N-Li 4,G-dimetoks ipyridin-2-yyli)aminokarbonyyli7-2,5-dibro-mibeiitseenisulfonami.di ·, sp. 2 01-2 04°C.E) for the selective control of weeds in rice are: 1) N - [(4-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 201-203 ° C; and 2) N-Li 4 (G-dimethoxypyridin-2-yl) aminocarbonyl] -2,5-dibromobenzenesulfonamide, mp 20-1204 ° C.
F) vesakon selektiiviseen torjuntaan on: 1) M - /"( 4 , 6-di;rie toks i -1 , 3 , 3 -1riat s in -2 - yyli ) aminokarbonyyliy'- be n t s ee n i s u 1 f onai mid i , sp. 18 3-18 b°C.F) for the selective control of vesicles is: 1) M - / "(4,6-di; triethoxy -1,3,3-1-triazin-2-yl) aminocarbonyl] benzene 1 mp 18 3-18 b ° C.
SynteesiSynthesis
Kuten yhtälössä 1 on esitetty, voidaan kaavan I yhdisteitä valmistaa saattamalla sopiva 2-aminopyrimidi.ini tai 2-amino-l, 3,5- 9 70577 triatsiini, joilla on kaava III, reagoimaan sopivan substituoidun su Ifonyy1i-isosyanaatin tai - isotiosyanaatin kanssa, jolla on kaava II; jolloin , W, X, Z ja R tarkoittavat samaa kuin edellä.As shown in Equation 1, compounds of formula I can be prepared by reacting the appropriate 2-aminopyrimidine or 2-amino-1,3,5-9,70577 triazine of formula III with the appropriate substituted sulfonyl isocyanate or isothiocyanate. of formula II; wherein, W, X, Z and R are as defined above.
Yhtälö 1Equation 1
WW
R1S02NCW + NH2-R -> R1SO?NHCNH-RR1SO2NCW + NH2-R -> R1SO2 NHCNH-R
(II) (III) (I)(II) (III) (I)
Reaktio saatetaan edullisesti tapahtumaan .inerteissä aproot-t.isissa orgaanisissa liuottimissa, kuten metyleenikloridissa, tet-rahydrofuraanissa tai asetonitriilissä, ympäristön paineessa ja lämpötilassa. Lisäämistapa ei ole ratkaiseva; usein on kuienkin sopivaa lisätä sulfonyyli-isosyanaatti tai -isotiosyanaatti amiinin III sekoituksenalaiseen suspensioon. Koska tällaiset isosyanaatit ja isotiosyanaatit tavallisesti ovat nesteitä, niiden lisäystä voidaan helposti säätää.The reaction is preferably carried out in inert aprotic organic solvents such as methylene chloride, tetrahydrofuran or acetonitrile at ambient pressure and temperature. The method of addition is not decisive; however, it is often convenient to add the sulfonyl isocyanate or isothiocyanate to the stirred suspension of amine III. Since such isocyanates and isothiocyanates are usually liquids, their addition can be easily adjusted.
Reaktio on yleensä eksoterminen. Joissakin tapauksissa haluttu tuote on liukenematon lämpimään reaktioväliaineeseen ja kiteytyy siitä puhtaassa muodossa. Reaktioväliaineeseen liukoiset tuotteet eristetään haihduttamalla liuotin, hiertämällä jähmeätä jäännöstä liuottimilla, kuten 1-klooributaanilla tai etyy1ieetterillä, ja suodattamalla.The reaction is usually exothermic. In some cases, the desired product is insoluble in the warm reaction medium and crystallizes therefrom in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as 1-chlorobutane or ethyl ether, and filtration.
Tietyissä tapauksissa on mahdollista, että edellä yhtälössä 1 esitetyn reaktion tuloksena on isomeerisia yhdisteitä, joita syntyy vähäisessä määrin yhdisteen II additioreaktiossa amiini III:n enaosyklisiin typpiatomeihin.In certain cases, it is possible that the reaction shown in Equation 1 above results in isomeric compounds which are formed to a small extent in the addition reaction of compound II to the enaocyclic nitrogen atoms of amine III.
Seuraavassa on esimerkkejä näiden rakennekaavoista: 10 70577 Λ Η ϊ \νThe following are examples of their structural formulas: 10 70577 Λ Η ϊ \ ν
RlSOaNHC-I^J>-X , ^SOatlHC-lt^-ZR1SOaNHC-I ^ J> -X, ^ SOatlHC-lt ^ -Z
ζ w ΝΗ II Μ ta] Hi-SOsNHC-IT^^irζ w ΝΗ II Μ ta] Hi-SOsNHC-IT ^^ ir
XX
On ymmärrettävä, että reaktiotuotteita, jotka saadaan kaavan II yhdisteen additiosta amiinien III eksosyklisiin sekä myös endosyklisiin typpiatomeihin, on pidettävä tämän keksinnön osana.It is to be understood that the reaction products obtained from the addition of a compound of formula II to exocyclic amines III as well as to endocyclic nitrogen atoms are to be considered as part of this invention.
Kaavan II välituote-sulfonyyli-isosyanaatteja (joissa W on 0) voidaan valmistaa saattamalla vastaavia sulfoniamideja reagoimaan fosgeenin kanssa n-butyyli-isosyanaatin läsnäollessa palautus-jäähdyttäen liuottimessa, kuten kiooribentseenissä , H. Ulrich'in ja A.A.Y. Sayigh’in, Newer Methods of Preparative Organic Chemistry Voi. VI s. 223-241, Academic Press, New York ja Lontoo, W. Foerst Ed. menetelmänmukaisesti tapauksissa, joissa haluttua sulfonyyli-isosyanaattia muodostuu pienellä sannnolla käyttäen esitettyä menetelmää, voidaan sulfonyyliurea, joka on muodostunut butyyli-isosya-naatin reaktiolla sopivan sulfoniamidin kanssa, saattaa reagoimaan fosgeenin kanssa kuten edellä olevassa viitteessä on kuvattu.Intermediate sulfonyl isocyanates of formula II (wherein W is 0) can be prepared by reacting the corresponding sulfonamides with phosgene in the presence of n-butyl isocyanate under reflux in a solvent such as chlorobenzene, H. Ulrich and A.A.Y. Sayigh, Newer Methods of Preparative Organic Chemistry Vol. VI pp. 223-241, Academic Press, New York and London, W. Foerst Ed. methodically, in cases where the desired sulfonyl isocyanate is formed in a low yield using the disclosed method, the sulfonylurea formed by the reaction of butyl isocyanate with the appropriate sulfonamide can be reacted with phosgene as described in the above reference.
Sulfoniamidien valmistusta ammoniumhydroksidista ja sulfo-nyyliklorideista on laajalti selostettu kirjallisuudessa, esim. Crossley et ai., J.Am.Chem.Soc., 60 2223 (1938). 2-furaanisulfoni-amidin valmistusta on kuvattu teoksessa J. Org. Chem., 18 894 (1953).The preparation of sulfonamides from ammonium hydroxide and sulfonyl chlorides has been extensively described in the literature, e.g., Crossley et al., J. Am. Chem. Soc., 60, 2223 (1938). The preparation of 2-furanesulfonamide is described in J. Org. Chem., 18, 894 (1953).
Tiettyjä s ui fonyy1iklorideja valmistetaan edullisesti kloo-risulfonoimalla joku substituoitu bentseeni, naftaleeni tai tio-feeni hiilitetrakloridissa H. T. Clarke et ai'in Org. Synth. Coll. Voi 1, toinen painos 1941, s. 85, oppien mukaisesti. Muita bentsee- n 70577 nisulfonyyliklorideja valmistetaan edullisesti diatsot isoirnalla sopiva uniliini natriumnitriiti 1 la HCl:ssä, mitä seuraa diatsonium-suolan reaktio rikkidioksidin ja kuprokloridin kanssa etikkahapossa H.L. Yale'n ja F. Sowinski'n, J. Org. Chem., 25 1824 (1960) oppien mukaisesti.Certain sulfonyl chlorides are preferably prepared by chlorosulfonation of a substituted benzene, naphthalene or thiophene in carbon tetrachloride according to the method of H. T. Clarke et al., Org. Synth. Coll. Volume 1, Second Edition 1941, p. 85, in accordance with doctrines. Other benzenesulfonyl chlorides of benzene 70577 are preferably prepared by diazotization of the appropriate uniline sodium nitrite in 1 L of HCl, followed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid H.L. Yale and F. Sowinski, J. Org. Chem., 25, 1824 (1960).
Furaanisulfonyyliklorideja valmistetaan edullisesti kuten yhtälössä 2 on esitetty.Furanesulfonyl chlorides are preferably prepared as shown in Equation 2.
Yhtälö 2 "Haö/HOl > fl\ (C0>so2ciEquation 2 "Haö / HOl> fl \ (C0> so2ci
Sulfonyyli-isotiosyanaatteja voidaan valmistaa käsittelemällä sulfoniamideja rikkihiilellä ja kaliumhydroksidilla, mitä seuraa dikaliumsuolan reaktio fosgeenin kanssa K. Hartke’nj Arch. Pharm., 299, 174 (1966), esityksen mukaisesti.Sulfonyl isothiocyanates can be prepared by treating sulfonamides with sulfur carbon and potassium hydroxide, followed by reaction of the dipotassium salt with phosgene K. Hartke’nj Arch. Pharm., 299, 174 (1966).
Heterosyklisten amiini-johdannaisten synteesiä on selostettu julkaisussa "The Chemistry of Heterocyclic Compounds", sarjassa, jota julkaisee Interscience Pubi., New York ja Lontoo. 2-aminopy-rimidiinejä on kuvannut D. J. Drown esitetyn sarjan osassa "The Pyrimidines", Voi., XVI.The synthesis of heterocyclic amine derivatives is described in "The Chemistry of Heterocyclic Compounds", a series published by Interscience Pub., New York and London. 2-Aminopyrimidines have been described by D. J. Drown in "The Pyrimidines", Vol., XVI.
Kaavan I yhdisteiden maanviljelyksellisesti sopivat suolat ovat myös hyödyllisiä rikkaruohomyrkkyjä ja niitä voidaan valmistaa monella alalla tunnetulla tavalla. Esimerkiksi metallisuoloja voidaan valmistaa käsittelemällä kaavan I yhdisteitä alkali- tai maa-alkalimetallisuolan, jossa on riittävän emäksinen anioni (esim. hydroksidin, alkoksidin, karbonaatin tai hydridin) liuoksella. Kvaternäärisiä amiinisuoloja voidaan valmistaa samanlaisilla menetelmillä .The agriculturally acceptable salts of the compounds of formula I are also useful herbicides and can be prepared in many ways known in the art. For example, metal salts can be prepared by treating compounds of formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be prepared by similar methods.
Kaavan I yhdisteiden suoloja voidaan valmistaa myös vaihtamalla yksi kationi toiseen. Kationin vaihto voidaan suorittaa käsittelemällä suoraan kaavan I yhdisteen suolan (esim. alkalimetalli-tai kvatermäärisen am.i inin suolan) vesiliuosta liuoksella, joka sisältää vaihdettavan kationin. Tämä menetelmä on erityisen tehokas, kun vaihdetun kationin sisältävä haluttu suola on liukenematon ve- 12 _ ΛSalts of the compounds of formula I can also be prepared by exchanging one cation for another. The cation exchange can be carried out by directly treating an aqueous solution of a salt of a compound of formula I (e.g. an alkali metal or quaternary amine salt) with a solution containing the cation to be exchanged. This method is particularly effective when the desired salt containing the exchanged cation is insoluble in water.
7057V7057V
teen ja voidaan erottaa nuodalt.imaila.I do and can be separated nuodalt.imaila.
Vaihto voidaan suorittaa myös kuljettamalla kaavan I yhdisteen suolan (esim. alkalimetalli- tai k.vaternänr i sen .1:-0 i ui n suolan) vesiliuos pylvään läpi, joka on täytetty kationin vaihtohartsilla, joka sisältää vaihdettavan kationin. Tässä menetelmässä hartsin kationi vaihdetaan alkuperäisen suolan kationiin ja haluttu tuote eluoidaan pylväässä. Tämä menetelmä on erityisen käyttökelpoinen kun haluttu suola liukenee veteen.The exchange can also be carried out by passing an aqueous solution of a salt of a compound of formula I (e.g. an alkali metal or k. Vernary salt thereof) through a column packed with a cation exchange resin containing the cation to be exchanged. In this method, the cation of the resin is exchanged for the cation of the original salt and the desired product is eluted in a column. This method is particularly useful when the desired salt is soluble in water.
Happoadd.it iosuol oja, jotka ovat käyttökelpoisia tässä keksinnössä, voidaan saada saattamalla kaavan I yhdiste reagoimaan sopivan hapon, esim. p-tolueenisulfonihapon , trikloorietikkahapon jne. kanssa.Acid addition salts useful in this invention can be obtained by reacting a compound of formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid, and the like.
Tämän keksinnön yhdisteitä ja niiden valmistusta kuvataan lähemmin seuraavin esimerkein, joissa lämpötilat ori annettu Celsiusasteissa .The compounds of this invention and their preparation are described in more detail in the following examples in which the temperatures of stallions are given in degrees Celsius.
Esimerkki 1 N - Z~( 1 , 6- dlmetyy 1 i pyr imidln-2-yy 11) aminokarbonyy 1 i,7 bent seeni-sulfoniamidiExample 1 N - Z - (1,6-Dimethylpyrimidin-2-yl) aminocarbonyl 1,7 Benzene sulfonamide
Kuivaan, hyvin sekoitettuun seokseen, jossa oli 12,4 g 2-amino-4,6-dimetyy1ipyrimidiiniä 250 ml:ssa metyleenikloridia, lisättiin ympäristön lämpötilassa ja paineessa tiputtaen 18,3 g bentseenisulfonyyli-isosyanaattia. Syntynyttä seosta sekoitettiin 2 tuntia ja saostunut tuote poistettiin suodatlamalla. Pesun jälkeen 1-klooributaanilla oli tuotteen sulamispiste 228-230° ja se antoi luonteenomaiset absorptionauhat infrapunakinjossa 1710 cm 1620 ^ ja 1550 emissä. Tuote oli N-[{4,6-dimetyy1ipyrimidin-2-yyli) ami nokarbonyy .1 p/bentseenisulf on i amid i .To a dry, well-stirred mixture of 12.4 g of 2-amino-4,6-dimethylpyrimidine in 250 ml of methylene chloride was added dropwise at ambient temperature and pressure 18.3 g of benzenesulfonyl isocyanate. The resulting mixture was stirred for 2 hours and the precipitated product was removed by filtration. After washing, 1-chlorobutane had a melting point of 228-230 ° of the product and gave characteristic absorption bands in the infrared chain of 1710 cm at 1620 and 1550 em. The product was N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide.
Esimerkki 2 N-/~( 4-metoksi-6-metyylipyr lmidin-2-yyli )aminokarbonyy 11_7 — 2 — klooribentseen isulfoniamidiExample 2 N- [4- (4-Methoxy-6-methyl-pyrimidin-2-yl) -aminocarbonyl] -2-2-chloro-benzenesulfonamide
Suspensioon, jossa oli 280 g 2-amino-4-metoksi-6-metyylipy-rimidiiniä 2000 mlrssa metyleenikloridia, lisättiin 434 g 2-kloori-bcntseenisulfonyyli-.i sosyanaa ttia sekoittaen. Syntynyttä seosta sekoitettiin 16 tuntia, jäähdytettiin 10°:eon ja suoda Lett i i n antamaan 470 g jätirneätä ainetta, joka suli 1.05-196°: ssa. Mnssaspektro-graaf ianalyys i osoitti tämän tuotteen molekyy lipainori olevan 356. Analyys i:To a suspension of 280 g of 2-amino-4-methoxy-6-methylpyrimidine in 2000 ml of methylene chloride was added 434 g of 2-chloro-benzenesulfonyl-cyanocyanate with stirring. The resulting mixture was stirred for 16 hours, cooled to 10 ° and filtered through Lett to give 470 g of a solid which melted at 1.05-196 °. Mnssaspektro-Graf analysis showed that the molecular weight of this product was 356. Analysis i:
Laskettu CINC^O S: lie: C, 4 3 , 80 %; H, 4,40 %; N, 15,75 %; Löydetty: C, 4 3 , 4 7 %; H, 3,56 N, 15,30 %.Calcd for CINC 2 O 5 S: C, 4, 80%; H, 4.40%; N, 15.75%; Found: C, 4 3, 4 7%; H, 3.56 N, 15.30%.
Tämä tuote oli N-/(4-metoksi-6-metyylipyrimidin-2-yyli)ami- 70577 nokarbonyy 1 i_/ - 2 - k loon' ben Lseon i su lion i ..iiii'i cl i .This product was N - [(4-methoxy-6-methylpyrimidin-2-yl) amin-70577] carbonyl-1H-2-clone ben Lseon i su lion i ..iiii'i cl i.
Suodosta haihduttamalla pienempään tilavuuteen, siitä saatiin saostumaan 20 g sivutuotetta, sp. 160-162°. Sivutuotteen infrapuna-absorptiokirja oli samanlainen kuin ensimmäisellä saostumalla ja sen molekyylipaino oli 356.Evaporation of the filtrate to a smaller volume gave 20 g of by-product, m.p. 160-162 °. The infrared absorption book of the by-product was similar to that of the first precipitate and had a molecular weight of 356.
Analyysi:Analysis:
Laskettu: C χ 3 H j 3C1N01(O^S: lie: C, 43,80 "o·, H, 3,40 N, 15,75 %; Löydetty: C, 44,09 X; H, 3,56 X; N, 14,97 X.Calculated: C, 3 H and 3 ClNO (O 2 S: C, 43.80 ° O, H, 3.40 N, 15.75%; Found: C, 44.09 X; H, 3.56 X, N, 14.97 X.
Käyttämällä ekvivalenttia määrää sopivaa 2-aminopyrimidiiniä ja sopivasti subs tituoitu bentseenisulfonyyli-isosyanaattia voidaan valmistaa seuraavat kaavan I yhdisteet esimerkkien 1 tai 2 menetelmillä : 1. 70577Using an equivalent amount of the appropriate 2-aminopyrimidine and an appropriately substituted benzenesulfonyl isocyanate, the following compounds of formula I can be prepared by the methods of Examples 1 or 2: 1. 70577
Taulukko I-ATable I-A
\ /R /CH3 „ ζ* o " /\ / R / CH3 "ζ * o" /
Atj------3 \ oC^NHCNH-^ .)Atj ------ 3 \ oC ^ NHCNH- ^.)
\ ' CH\ 'CH
R4 R3 LH3 F R R I? R s p.R4 R3 LH3 F R R I? R s p.
r'3 4 1 b 7 p H H H H H 7 ? 8 - ? 31 F H H H H 718-719 CH3 H H H H 19 5-19 or'3 4 1 b 7 p H H H H H 7? 8 -? 31 F H H H H 718-719 CH3 H H H H 19 5-19 p
Cl H H H H 2U4-205 H H H NO,, H 19 3-196 H H H 0Γ3 H 183(U) H Cl H H H 142-143 -CF3 H H H H 218-222 CH 0 H H CH.S0o H 300-203(d)Cl H H H H 2U4-205 H H H NO ,, H 19 3-196 H H H 0Γ3 H 183 (U) H Cl H H H 142-143 -CF3 H H H H 218-222 CH 0 H H CH.S0o H 300-203 (d)
ChT30- H CHO- H H 198-199 CH3 H H N0? H 191-192 CH0 H H -CH(CH„)„H 157-162ChT30- H CHO- H H 198-199 CH3 H H N0? H 191-192 CH0 H H -CH (CH2) „H 157-162
O ö ZO ö Z
CHq H H Cl H 709-211CHq H H Cl H 709-211
Cl H H CH H 211-213 F H H F H 189-190 CH30- H H CH3 H 193-194Cl H H CH H 211-213 F H H F H 189-190 CH30- H H CH3 H 193-194
Cl H H H CH 2 3 G - 2 3 7 NO. H Cl H H 710-212 «iCl H H H CH 2 3 G - 2 3 7 NO. H Cl H H 710-212 «i
Cl H H II Cl 177-18 2 F H H H F 228-211Cl H H II Cl 177-18 2 F H H H F 228-211
Cl Cl Cl H H 315-217Cl Cl Cl H H 315-217
Cl H Cl Cl H 294-205 -CH(CH^). H Cl -CH(CH3)7H 131-136 70577 1 5 R3 R,4 Rb R6 R7 Sp' C H SO,,- H H H H kumi Z O zCl H Cl Cl H 294-205 -CH (CH 2). H Cl -CH (CH3) 7H 131-136 70577 1 5 R3 R, 4 Rb R6 R7 Sp 'C H SO ,, - - H H H H rubber Z O z
CH3S02- h H h h 2 08 -2 1 UCH3SO2- h H h h 2 08 -2 1 U
CH H CH H CH,. 227-231(d)CH H CH H CH ,. 227-231 (d)
O vJO vJ
F H F H F 173-182F H F H F 173-182
Cl H Cl H Cl 288-210 CH30- H CH30- H CH 0- 192-193Cl H Cl H Cl 288-210 CH30- H CH30- H CH 0- 192-193
Cl Cl H Cl Cl 220-222 CH3 CH3 H CH3 CH3 2 4 0-21(6Cl Cl H Cl Cl 220-222 CH3 CH3 H CH3 CH3 2 4 0-21 (6
Cl Cl H H H 195-197Cl Cl H H H 195-197
Cl CH3 H H H 196-199 CH30- Cl H H H 179-180 F Cl H H H 196-197 CH3 Cl H H II 708-209Cl CH3 H H H 196-199 CH30- Cl H H H 179-180 F Cl H H H 196-197 CH3 Cl H H II 708-209
Cl H Cl H H 202-225 F H Cl H H 202-203 H Cl Cl H H 210-212' H Cl H Cl H 199-202 CH30 H Cl CH30 H 202-203 F H H CH3 H 210-212 CH3 H H F H 200-201Cl H Cl H H 202-225 F H Cl H H 202-203 H Cl Cl H H 210-212 'H Cl H Cl H 199-202 CH30 H Cl CH30 H 202-203 F H H CH3 H 210-212 CH3 H H F H 200-201
Cl H H CH3°- H 198-199Cl H H CH 3 ° - H 198-199
Br H H Br H 211-212 CH30- H H ch3 °- H 193-195 CH3 H H CH3 H 204-275 CH3 H H Br H 205-207 C„H 0- H H C,Hl0- H 208-210 /5 2 b CH30- H H F H 199-201Br HH Br H 211-212 CH30- HH ch3 ° - H 193-195 CH3 HH CH3 H 204-275 CH3 HH Br H 205-207 C „H 0- HHC, H10- H 208-210 / 5 2 b CH30- HHFH 199-201
Cl H H Cl H 212-213 CH,}CH2CH?0 H H CH3CH2CH2OH 150-152 CH.,0- H H Cl H 209-210 CHl CH,, H NOo H 2 2 1- 2 2 3 O J z 70577Cl H H Cl H 212-213 CH,} CH2CH2 O H H CH3CH2CH2OH 150-152 CH., 0- H H Cl H 209-210 CH1 CH ,, H NOo H 2 2 1- 2 2 3 O J z 70577
1 G1 G
Taulukko I-BTable I-B
R6 k - N—< 7 0 N ,/°CH3R6 k - N - <7 0 N, / ° CH3
R. - -oCR.NHCNHR. - -oCR.NHCNH
V:--< 2 vy k k k_k_r5 r6_k_SP- H H H H H 204-205 H CH3 H H H 149-151V: - <2 vy k k k_k_r5 r6_k_SP- H H H H H 204-205 H CH3 H H H 149-151
Br H H H H 210-211 F H H H H 198-199 CH30 H H H H 178-180 CH3 H H H H 172-174Br H H H H 210-211 F H H H H 198-199 CH30 H H H H 178-180 CH3 H H H H 172-174
Cl H H H H 206-207 CN H H H H 154-156 -S02CH3 H H H H 170-171 H Cl H H H 151-153 H H H CH3 H 150-152Cl H H H H 206-207 CN H H H H 154-156 -SO2CH3 H H H H 170-171 H Cl H H H 151-153 H H H CH3 H 150-152
Cl H H CN H 203 — 205(d) CH3 H H ~S02CH3 H 182-184Cl H H CN H 203 - 205 (d) CH 3 H H ~ SO 2 CH 3 H 182-184
Cl Cl H H H 199-200Cl Cl H H H 199-200
Cl CH3 H H H 177-186 CH30- Cl H H H 190-193 CH Cl H H H 190-192 F Cl H H H 193-195 H Cl Cl H H 193-195 n-C^HgO- H H n-C4HgO- H 182-183 F H Cl H H 206-208 NOg H H H H 223-225 CF3 H H H H 194-197Cl CH3 HHH 177-186 CH30- Cl HHH 190-193 CH Cl HHH 190-192 F Cl HHH 193-195 H Cl Cl HH 193-195 nC ^ HgO- HH n-C4HgO- H 182-183 FH Cl HH 206- 208 NOg HHHH 223-225 CF3 HHHH 194-197
Cl H F H H 199-201Cl H F H H 199-201
Cl H Cl H H 195-197Cl H Cl H H 195-197
Cl H CH30 H H 201-202 CH3 Cl H Cl H 187-189 CH3Q H CHgO H H 182-184 70577 _N__^7_Sp ' H H CH30 N02 H 211-213 H Cl H Cl H 207-211 H CH3 CH3 H H 193-196 F H H F H 177-178 CH30- H H Cl H 199-200 CH3 H H Cl H 206-207 C„HcO- H H C„H O- H 175-177Cl H CH30 HH 201-202 CH3 Cl H Cl H 187-189 CH3Q H CHgO HH 182-184 70577 _N __ ^ 7_Sp 'HH CH30 NO2 H 211-213 H Cl H Cl H 207-211 H CH3 CH3 HH 193-196 FHHFH 177-178 CH30- HH Cl H 199-200 CH3 HH Cl H 206-207 C „HcO- HHC„ H O- H 175-177
Cl H H CH3 H 197-200 CH3 H H N02 H 194-195 CH3 H H -CH(CH3)2 H 136-142Cl H H CH3 H 197-200 CH3 H H NO2 H 194-195 CH3 H H -CH (CH3) 2 H 136-142
Cl H H N02 H 178-180 CH3 H H CH3 H 174-176 CH H H Br H 195-197Cl H H NO 2 H 178-180 CH 3 H H CH 3 H 174-176 CH H H Br H 195-197
OO
Br H H Br H 207-209 CH 0- H H CH O- H 175-177Br H H Br H 207-209 CH 0- H H CH O- H 175-177
o Oo O
Cl H H Cl H 174-179 F H H CH3 H 207-208 CH3 H H F H 173-175Cl H H Cl H 174-179 F H H CH3 H 207-208 CH3 H H F H 173-175
Cl H H CH3°- H 199-200 CH30- H H CH3 H 180-182 F H H H F 192-195Cl H H CH3 ° - H 199-200 CH30- H H CH3 H 180-182 F H H H F 192-195
Cl H H H Cl 148-153Cl H H H Cl 148-153
Cl H H H CH3 166-170 CH3S02- H H H H 170 C H SO - H H H H kumi 2-0 L·.Cl H H H CH3 166-170 CH3SO2- H H H H 170 C H SO - H H H H rubber 2-0 L ·.
CH3S- H H H H 200-202 C„H 0- H H Cl H 180-183 2 5 CH30 H Cl CH30 H 173-175 CH3CH2CH20 H H CH3CH2CH20 H 173-175 CH3S H H Cl H 215-216 CH3 CH3 H N02 H 191-193CH3S- H H H H 200-202 C „H 0- H H Cl H 180-183 2 5 CH30 H Cl CH30 H 173-175 CH3CH2CH2O H H CH3CH2CH2O H 173-175 CH3S H H Cl H 215-216 CH3 CH3 H NO2 H 191-193
Cl Cl Cl H H 186-187Cl Cl Cl H H 186-187
Cl H Cl Cl H 189-190 CH3 H CH3 H CH3 203-205 18 70577 _^4__SP‘ F H F H F 197-199Cl H Cl Cl H 189-190 CH3 H CH3 H CH3 203-205 18 70577 _ ^ 4__SP ‘F H F H F 197-199
Cl H Cl H Cl 181-186 CH30- H CH3°- H CH30 185-187Cl H Cl H Cl 181-186 CH 3 O- H CH 3 O - H CH 3 O 185-187
Cl Cl H Cl Cl 215-218 CH3 CH3 H CH3 CH3 223-226 CH30 Cl H Cl H 181-183 CH3 Cl H N02 H 182-183Cl Cl H Cl Cl 215-218 CH3 CH3 H CH3 CH3 223-226 CH30 Cl H Cl H 181-183 CH3 Cl H NO2 H 182-183
Taulukko I-CTable I-C
V . R,V. R:
' 2 /-N V'2 / -N V
R --( / CO NHCNH -( 5 \ — -/ 2 NC17 / \ X o c1 ] V r3 ocj3 _R5 R6_R7 SP· H H H H H 202-203 F H H H H 200-201R - (/ CO NHCNH - (5 \ - - / 2 NC17 / \ X o c1] V r3 ocj3 _R5 R6_R7 SP · H H H H H 202-203 F H H H H 200-201
Cl H H H H 179-181 CH3 H H H H 185-186 CH3S02 H H H CH3 200-202,5 S02C2H5 H H H H kumi H Cl H H H >250 H H H CF3 H 190-191Cl H H H H 179-181 CH3 H H H H 185-186 CH3SO2 H H H CH3 200-202.5 SO2C2H5 H H H H rubber H Cl H H H> 250 H H H CF3 H 190-191
Cl H H CN H 215-217 F H H H F 213-215Cl H H CN H 215-217 F H H H F 213-215
Cl H H H Cl 192-194 N02 H Cl H H 196-198 NO H H H H 219-220 CH3S H H Cl H 211-213 CH 0- Cl H H H 183-184 0 F Cl H H H 244-245 F H Cl H H 223-2 24Cl H H H Cl 192-194 NO2 H Cl H H 196-198 NO H H H H 219-220 CH3S H H Cl H 211-213 CH 0- Cl H H H 183-184 0 F Cl H H H 244-245 F H Cl H H 223-2 24
Cl H F H H 203-205Cl H F H H 203-205
Cl H Cl li H 190-191 CH30- H C H 3 °- H H 182-184 19 70577 R0 R., Rc Rr R„ sp.Cl H Cl li H 190-191 CH30- H C H 3 ° - H H 182-184 19 70577 R0 R., Rc Rr R „sp.
3_4_o_b_/___ CH30- H H CH3 H 227-2293_4_o_b _ / ___ CH30- H H CH3 H 227-229
Cl H H CF3 H 161-162 F H H F H 210-212Cl H H CF3 H 161-162 F H H F H 210-212
Br H H Br H 201-204 CH30- H H ch3°- H 198-199 CH H H Br H 170-172Br H H Br H 201-204 CH30- H H ch3 ° - H 198-199 CH H H Br H 170-172
Cl H H N02 H 225-228Cl H H NO 2 H 225-228
Cl H H CHgO- H 180-181 C3H?0- H H C3H7° H 188-189 n-C H O- H H n-C^HgO- H 165-167 C H O- H H C H O- H 181-183 l o l o CHgO- H H F H 192-194 CH30- H H Cl H 197-198Cl HH CHgO- H 180-181 C3H? 0- HH C3H7 ° H 188-189 nC H O- HH nC ^ HgO- H 165-167 CH O- HHCH O- H 181-183 lolo CHgO- HHFH 192-194 CH30 - HH Cl H 197-198
Cl H H Cl H 189-190 CHg H H Cl H 181-183Cl H H Cl H 189-190 CHg H H Cl H 181-183
Cl H H CHg H 216-217 CHg H H NOg H 205-207 CHg H H -CH(CH3)2 H 110-116 CH H H CHg H 187-189 CHgO- H CHgO- H H 173-175 CHgO H H H H 193-195 CHgO H Cl CHgO H 141-143 CHg Cl H Cl H 186-189 (CHg)2CH H H (CHg)2CH H 161-163 CHgS H H H H 211-214 H H CHgO NOg H 210-212Cl HH CHg H 216-217 CHg HH NOg H 205-207 CHg HH -CH (CH3) 2 H 110-116 CH HH CHg H 187-189 CHgO- H CHgO- HH 173-175 CHgO HHHH 193-195 CHgO H Cl CHgO H 141-143 CHg Cl H Cl H 186-189 (CHg) 2CH HH (CHg) 2CH H 161-163 CHgS HHHH 211-214 HH CHgO NOg H 210-212
Cl H H H CHg 171-174 CHg H CHg H CHg 197-198 F H F H F 219-221Cl H H H CHg 171-174 CHg H CHg H CHg 197-198 F H F H F 219-221
Cl H Cl H Cl 194-195 CHgO- H CHgO- H CHgO- 180-181Cl H Cl H Cl 194-195 CHgO- H CHgO- H CHgO- 180-181
Cl Cl H Cl Cl 223-2 24 CHg CHg H CHg CHg 182~184 CFg H H H H 219-220 CHgO Cl H Cl H 183-185 CHg Cl H NOg H 207-209 CH3 CH3 H NOg H 225-227 70577 20Cl Cl H Cl Cl 223-2 24 CHg CHg H CHg CHg 182 ~ 184 CFg H H H H 219-220 CHgO Cl H Cl H 183-185 CHg Cl H NOg H 207-209 CH3 CH3 H NOg H 225-227 70577 20
Taulukko I-DTable I-D
° ; <c”3 r5—(_)_so2ncnh -/ ) >-\ H N ~\°; <c ”3 r5 - (_) _ so2ncnh - /)> - \ H N ~ \
R " R XXR "R XX
4 3 R3 R4 R5 r6 r7 X sp.4 3 R3 R4 R5 r6 r7 X sp.
H H H H H H 187-189 CH3 H H H H -CII2OCH3 15 7-138H H H H H H 187-189 CH3 H H H H -CII2OCH3 15 7-138
Cl H H H H -CH.,0CHo 179-18!;Cl H H H H -CH., 0CHo 179-18 !;
2 O2 O
Cl H H Cl H -CH.OCII 174-176 CHo0- H H CH 0- H -CH„0CHQ 155-157 5 3 i 3 F H H H H H 192-193 CH3 H H H H H 211-213Cl H H Cl H -CH.OCII 174-176 CHo0- H H CH 0- H -CH „0CHQ 155-157 5 3 i 3 F H H H H H 192-193 CH3 H H H H H 211-213
Cl H H H H H 2 01-2 03 H Cl H H H H 198-199 F Cl H H H H 219-220 CH3 Cl H H H H 211-213 F H Cl H H H 222 — 235(d) H Cl H Cl H H 201-203 CH30- H H Cl H H 224-226Cl H H H H H 2 01-2 03 H Cl H H H H 198-199 F Cl H H H H 219-220 CH3 Cl H H H H 211-213 F H Cl H H H 222 - 235 (d) H Cl H Cl H H 201-203 CH30- H H Cl H H 224-226
Cl H H Cl H H 207-209 CH3 H H Cl H H 217-219 F H H F H H 173-199Cl H H Cl H H 207-209 CH3 H H Cl H H 217-219 F H H F H H 173-199
Cl H H H Cl H 160-163 H H H H H C0Hc 0- 180-182 l b CH3 H H CIi3 H C2H5°- 130-134 H H H H H (CH3)2CHO- 116-120 H H H H H Cl. 213-215 H Cl H H H Cl 194-195 H H H H H CH3S- 208(d) K H H H H -CF3 179-182 CH 3 H H II H -CF.j 172-174Cl H H H Cl H 160-163 H H H H H C0Hc 0-180-182 l b CH3 H H Cli3 H C2H5 ° - 130-134 H H H H H (CH3) 2CHO- 116-120 H H H H H Cl. 213-215 H Cl H H H Cl 194-195 H H H H H CH3S- 208 (d) K H H H H -CF3 179-182 CH 3 H H II H -CF.j 172-174
Cl H H H H -CFQ 17 3-17 5 21 70577 R3 K4 RS R6 R7 X Sp’ H H H -CF3 H -CF3 160-163 N02 H H H H Cl 17 0-17 2Cl H H H H -CFQ 17 3-17 5 21 70577 R3 K4 RS R6 R7 X Sp 'H H H -CF3 H -CF3 160-163 NO2 H H H H Cl 17 0-17 2
Taulukko I-ETable I-E
/ R7 0CH3 6\.-/ > 0 N -< d r -Γ >—SO.NHCNH-Γ x> 5 W 2 \n^/ T R3 R0 R,, Rc Rc R^ X sp./ R7 0CH3 6 \ .- /> 0 N - <d r -Γ> —SO.NHCNH-Γ x> 5 W 2 \ n ^ / T R3 R0 R ,, Rc Rc R ^ X m.p.
o 4 o b / H H H H H H 199-200(d) H H H H H Cl 181-183o 4 o b / H H H H H H 199-200 (d) H H H H H Cl 181-183
Cl H H H H Cl 185-188 CH3 H H H H Cl 176-178Cl H H H H Cl 185-188 CH3 H H H H Cl 176-178
Cl H H Cl H Cl 20 2-2 05 H H H H H CH^S- 199-196Cl H H Cl H Cl 20 2-2 05 H H H H H CH ^ S- 199-196
Cl H H H H CH3S" 195-199 H H H H H -CF3 164-168Cl H H H H CH3S "195-199 H H H H H -CF3 164-168
Cl H H H H -CF3 204-208 CH3 H H H H -CF3 171-173 H H H -CF3 H -CF3 191-194 H H H H H C2H5°" 163-165Cl H H H H -CF 3 204-208 CH 3 H H H H -CF 3 171-173 H H H -CF 3 H -CF 3 191-194 H H H H H C 2 H 5 ° "163-165
Cl H H H H C„Hr0- 142-144 2 5 CH, H H H H C„Ht 0- 148-149Cl H H H H C „Hr0- 142-144 2 5 CH, H H H H C„ Ht 0- 148-149
o ZDo ZD
22 7057722 70577
Esimerkki 3 N-Z.T 4 ,6-dimetyyl.ipyrimidin-2-yyli)aminoka,rbonyylll7-2-tio-feenisulfoniamidi 12 g:aan 2-amino-4,6-dimetyylipyrimidiiniä 2 50 ml: ssa asetonit- riiliä lisättiin sekoittaen 19 g 2-tiofeenisulfonyyli-isosyanaattia.Example 3 NZ.T (4,6-dimethyl-pyrimidin-2-yl) -amino] -fonyl] -2-thiophenesulfonamide To 12 g of 2-amino-4,6-dimethyl-pyrimidine 2 in 50 ml of acetonitrile was added with stirring. g of 2-thiophenesulfonyl isocyanate.
Syntynyttä seosta sekoitettiin 2 tuntia ja suodatettiin antamaan haluttu jähmeä tuote, sp. 211-216°. Infrapunakirjo tälle tuotteelle -1 -1 1 antoi absorptiohuiput 1540 cm , 1605 cm ja 1700 cm :ssä.The resulting mixture was stirred for 2 hours and filtered to give the desired solid product, m.p. 211-216 °. The infrared spectrum for this product -1 -1 L gave absorption peaks at 1540 cm, 1605 cm and 1700 cm.
Esimerkki 4 N-il4 ,6-dimetyylipyrimidin-2-yyli)aminokarbonyylU-2,5-di- kloori-3-tiofeenisulfoniamidiExample 4 N-yl (2,6-dimethylpyrimidin-2-yl) aminocarbonyl-2,5-dichloro-3-thiophenesulfonamide
Suspensioon, jossa oli 12 g 2-amino-4,6-dimetyylipyrimidiiniä 300 ml:ssa metyleenikloridia, lisättiin ympäristön lämpötilassa 26 g 2,5-dikl oori-3-tiofeenisulfonyyli-isosyanaattia. 16-tuntisen sekoittamisen jälkeen saatu liuos haihdutettiin kuiviin ja haluttu tuote, joka saatiin jähmeänä jäännöksenä, hierrettiin etyylieetteril- lä ja suodatettiin. Näin saatu jähmeä tuote suli 192-194°:ssa ja se -1 -1 1 antoi infrapuna-absorptiohuiput 1550 cm , 16G5 cm ja 1690 cm :ssä. Esimerkki 5 N-/.( 4-metoksi-6-metyylipyrimidin-2-yyli)aminokarbonyylΓ7-2-furaanisulfoniamidiTo a suspension of 12 g of 2-amino-4,6-dimethylpyrimidine in 300 ml of methylene chloride was added 26 g of 2,5-dichloro-3-thiophenesulfonyl isocyanate at ambient temperature. After stirring for 16 hours, the resulting solution was evaporated to dryness and the desired product obtained as a solid residue was triturated with ethyl ether and filtered. The solid product thus obtained melted at 192-194 ° and gave -1 -1 L of infrared absorption peaks at 1550 cm, 16G5 cm and 1690 cm. Example 5 N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-furansulfonamide
Liuokseen, jossa oli 2,10 g 2-furaanisulfonyyli-isosyanaattia UC ml:ssa metyleenikloridia, lisättiin 1,60 g 2-amino-4-metoksi-6-metyylipyrimidiiniä. Saatua seosta sekoitettiin 1 tunti huoneen lämpötilassa, kuumennettiin sitten palautusjäähdyttäen 15 minuuttia ja liuotin poistettiin tyhjössä. Saadun jähmeän aineen annettiin seistä etyylieetterissä, joka sisälsi pienen määrän asetonitriiliä yhden päivän ajan ja suodatettiin sitten ja kuivattiin antamaan haluttu tuote, joka suli 185-188°:ssa (hajoten). Käyttämällä ekvivalenttia määrää sopivaa 2-aminopyrimidiiniä ja sopivasti substituoi-tua tiofeeni- tai furaanisulfonyyli-isosyanaattia, voidaan valmistaa seuraavat taulukon II yhdisteet esimerkkien 3-5 menetelmällä:To a solution of 2.10 g of 2-furansulfonyl isocyanate UC in ml of methylene chloride was added 1.60 g of 2-amino-4-methoxy-6-methylpyrimidine. The resulting mixture was stirred for 1 hour at room temperature, then heated to reflux for 15 minutes and the solvent removed in vacuo. The resulting solid was allowed to stand in ethyl ether containing a small amount of acetonitrile for one day and then filtered and dried to give the desired product, melting at 185-188 ° (dec). Using an equivalent amount of the appropriate 2-aminopyrimidine and an appropriately substituted thiophene or furansulfonyl isocyanate, the following compounds of Table II can be prepared by the method of Examples 3-5:
IIII
23 7 0 5 7 723 7 0 5 7 7
Taulukko II-ATable II-A
0 N X0 N X
ft %S0.NHC-NH /7 X\___,ft% S0.NHC-NH / 7 X \ ___,
(N7 2 W(N7 2 W
Rg Q X Z sp.Rg Q X Z m.p.
H S CHg CHgO- 207-208 H S CH3 °- ch3°- 206-2 07H S CHg CHgO- 207-208 H S CH3 ° - ch3 ° - 206-2 07
Cl S CHg CH30- 186-187Cl S CHg CH30- 186-187
Cl S CH3 CHg 198-199Cl S CH3 CHg 198-199
Cl S H CHg 197-198 CHg S CHg CHg 0- 132-144 CHg S CHg 0- CH g °- 159-169 H 0 CHg CHg 0 185-188Cl S H CHg 197-198 CHg S CHg CHg 0- 132-144 CHg S CHg 0- CH g ° - 159-169 H 0 CHg CHg 0 185-188
Taulukko II-BTable II-B
° /" x/X SOjNHCNhV ') — H° / "x / X SOjNHCNhV ') - H
Γ\ N"\z V" R10Γ \ N "\ z V" R10
Rg R10 X z sp'Rg R10 X z sp '
Cl Cl CHg CHgO- 186-188Cl Cl CHg CHgO- 186-188
Cl Cl CHg °- CHgO- 201-202Cl Cl CHg ° - CHgO- 201-202
Br Br CHg CHg 188-195 2* 70577Br Br CHg CHg 188-195 2 * 70577
Esimerkki 6 Ν~£Γ!ι, 6-d imet ok s ipyrimidin - 2 -yyli ) am, irjokar bony y lii1-1-naf t a -leenisulfoniamidiExample 6 (6-Dimethylpyrimidin-2-yl) amine carbonyl] -1-naphthalenesulfonamide
Suspensioon, jossa oli Ib,6 g 2-amino-4,6-dimetoksipyrimidii-niä 4 CO ml:ssa asetonitriiliä, lisättiin sekoittaen 23,3 g 1-nafta-leenisulfonyyli-isosyanaattia. Jatketun 14-tuntisen sekoittamisen jälkeen poistettiin haluttu jähmeä tuote suodattamalla ja pesun jälkeen pienellä määrällä etyy1ioetteriä se suli 177-178°C:ssa.To a suspension of Ib, 6 g of 2-amino-4,6-dimethoxypyrimidine in 4 ml of acetonitrile was added with stirring 23.3 g of 1-naphthalenesulfonyl isocyanate. After stirring for 14 hours, the desired solid was removed by filtration and, after washing with a small amount of ethyl ether, melted at 177-178 ° C.
Käyttämällä ekvivalenttia määrää sopivaa 2-aminopyrimidiiniä ja l-naftaaeenisulfonyyli-isosyanaattia voidaan valmistaa seuraavat kaavan I yhdisteet esimerkin 6 menetelmällä: N- /_( 4-kloori - 6-metyyl ipyrimidin - 2- yy li) aminokar bony yli./ -1-naf talee-nisulfoniamidi, sp. 235-207° N-/_( 4 , 6-d imet yyl ipyr im id in- 2-yyl i ) aminokarbonyy 117 -1-naf tale enisul-foniamidi, sp. 201-202° N- il_4-metyylipyr imidin-2-yyli) aminokarbonyy 1^7-1-naftaleenisulf on i-amidi, sp. 132-183° N-jQ 4-me toks i-6-metyy1ipyrimid in-2-yyli)aminokarbonyy1ι7-1-naft alee-nisulfoniamidi, sp. 210-211°Using an equivalent amount of the appropriate 2-aminopyrimidine and 1-naphthalenesulfonyl isocyanate, the following compounds of formula I can be prepared by the method of Example 6: N- (4- (4-chloro-6-methylpyrimidin-2-yl) aminocarbonyl). naphthalenesulfonamide, m.p. 235-207 ° N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 201-202 ° N-yl-4-methylpyrimidin-2-yl) aminocarbonyl (1-7-1-naphthalenesulfone i-amide, m.p. 132-183 ° N- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl-1-naphthalenesulfonamide, m.p. 210-211 °
Esimerkki 7 N-IS 3 > 6-dimetyyl.ipyrimidin-2-yyli)aminotioksometyylf/'bentseeni- sulfonamidiExample 7 N-IS 3 (6-dimethylpyrimidin-2-yl) aminothioxomethyl (benzenesulfonamide)
Kuivaan suspensioon, jossa oli 12,4 g 2-amino-4,6-dimetyyli-pyrimidiiniä υ3 ml:ssa asetonitriiliä, lisättiin 19,9 g bentseeni-sulfonyyli-isotiosyanaattia. Muodostunut raskas saostuma poistettiin suodattamalla ja pestiin vedettömällä etyylieetterillä. Se suli 165-1/0 :ssa. Tuote oli N-/S 4,6-dimetyylipyrLmidin-2-yyli)-amino-t ioksometyy l_l_/ bent s e en i su If on iamid i .To a dry suspension of 12.4 g of 2-amino-4,6-dimethylpyrimidine in 3 ml of acetonitrile was added 19.9 g of benzenesulfonyl isothiocyanate. The resulting heavy precipitate was removed by filtration and washed with anhydrous ethyl ether. It melted at 165-1 / 0. The product was N- (S (4,6-dimethylpyrimidin-2-yl) amino-dioxomethyl) benzene is an amide.
Käyttämällä ekvivalenttia määrää sopivaa sulfonyyli-isotio-syanaattia ja sopivasti substituoitua aminopyrimidiiniä voidaan valmistaa taulukon III yhdisteitä esimerkin 7 menetelmällä: 2s 70577Using an equivalent amount of the appropriate sulfonyl isothiocyanate and appropriately substituted aminopyrimidine, the compounds of Table III can be prepared by the method of Example 7: 2s 70577
Taulukko III-ATable III-A
Rfi D o Λ N-Λ N -rf' R^/^)-S02NHC-Mi</ _\ R0 R Rc Rc R-, X Z sp.Rfi D o Λ N-Λ N -rf 'R ^ / ^) - SO2NHC-Mi </ _ \ R0 R Rc Rc R-, X Z sp.
H H H H H CH3 cH30- 188-189 H H H H H CH30 CH30 192-193H H H H H CH3 cH30- 188-189 H H H H H CH30 CH30 192-193
Cl H H H H CH3 ch3°- 184-185Cl H H H H CH3 ch3 ° - 184-185
Cl H H H H CH3°“ CH30- 169-172 CH3 H H H H CH3 CH30 165-167 CH3 H H H H CH3°- CH30- 181-182 CH30- H H ch3 0- H CH3 CH30- 178-180 CH30- H H CH30 - H CH30- ch3°- 191-193Cl HHHH CH3 ° “CH30- 169-172 CH3 HHHH CH3 CH30 165-167 CH3 HHHH CH3 ° - CH30- 181-182 CH30- HH ch3 0- H CH3 CH30- 178-180 CH30- HH CH30 - H CH30- ch3 ° - 191-193
Taulukko IIT-BTable IIT-B
/M\ " /Λ/ M \ "/ Λ
Rg X Z sp.Rg X Z m.p.
H CH3 ch3°- 196-197 H CH3°- ch3°- 202-204 CH3 CH3 ch3 C- 132-144 CH3 CH30_ CH3°" 159-169 26 70577H CH3 ch3 ° - 196-197 H CH3 ° - ch3 ° - 202-204 CH3 CH3 ch3 C- 132-144 CH3 CH3O_CH3 ° "159-169 26 70577
Esimerkki. 8 2-furaanisu!fonyyli-isosyanaatti // v. nBuLi_____\ // \\ h' h \ 0/ Et20, RT '-o^Li '3° V-O/XS02LiExample. 8 2-Furanisulfonyl isocyanate // v. NBuLi _____ \ // \\ h 'h \ 0 / Et 2 O, RT' -o ^ Li '3 ° V-O / XS02Li
Ce,_^ lf~i NH^OH jj \ ylimäärä (C0C1) 2 ^Excess (COCl) 2 ^ Ce, _ ^ lf ~ i NH ^ OH jj \
Ho0 , HC1X , \ 0-5 ^ Λ - \ 2 o so2ci 0 so2nh2 r\ Ό' ^S02NC0 A. Litium-2-furaanisulfinaattiHo0, HC1X, \ 0-5 ^ Λ - \ 2 o so2ci 0 so2nh2 r \ Ό '^ SO2NC0 A. Lithium 2-furan sulfinate
Liuokseen, jossa oli 39,6 p furaania ( 585 ml) 200 ml:ssa vedetöntä etyylieetteriä, lisättiin varovasti typpiatmosfäärissä 100 ml 1,6 M n-butyylil i tämiä heksaanissa, pitäen samalla reaktio-lämpötila 30 :ssa tai alempana. Seosta sekoitettiin kunnes saostuminen näytti täydelliseltä. Jäähdyttämisen jälkeen -25-30°:een johdettiin kaasumaista rikkidioksiidia hitaasti seoksen läpi kahden tunnin ajan. Seosta sekoitettiin huoneen lämpötilassa vielä 90 minuuttia ja saostunut 1itium-2-furaanisulfinaatti suodatettiin ja pestiin asetonialla. Sp. 250°. Infrapunakirjo IR (Nujol) 3100-3000 cm"1 (W), 1700 cm-1, 1550 cm"1 (VW), 1210 cm"1, 1110 cm"1, 1115 cm'1 (m), 1020 cm"1 (VS), 91 fJ cm"1 , 880 cm"1 , 8 25 cm"1 (W), 7 3 5 cm"1 (S).To a solution of 39.6 g of furan (585 mL) in 200 mL of anhydrous ethyl ether was carefully added 100 mL of 1.6 M n-butyl in hexane under a nitrogen atmosphere while maintaining the reaction temperature at 30 or below. The mixture was stirred until precipitation appeared complete. After cooling to -25-30 °, gaseous sulfur dioxide was slowly passed through the mixture for two hours. The mixture was stirred at room temperature for an additional 90 minutes and the precipitated lithium 2-furansulfinate was filtered and washed with acetone. Sp. 250 °. Infrared spectrum IR (Nujol) 3100-3000 cm -1 (W), 1700 cm -1, 1550 cm -1 (VW), 1210 cm -1, 1110 cm -1, 1115 cm -1 (m), 1020 cm -1 (VS), 91 fJ cm -1, 880 cm -1, 8 25 cm -1 (W), 7 3 5 cm -1 (S).
?7 70577 13. 7 - f u raan is u 1 f onyy 11 kloridi 90 ml vettä, 410 ml väkevää HC1 ja 6 8,0 g 1 i tiurn-2-f uraani-sulfinaattia sekoitettiin mekaanisesti ja jäähdytettiin 10-15°:een. Nestemäistä klooria (12,3 ml, 39,4 g) lisättiin tiputtaen 30 minuutin aikana. Seosta sekoitettiin vielä 30 minuuttia 5°C:ssa, kaadettiin jäihin ja uutettiin metyleenikloridilla. Metyleenikloridin haihduttaminen antoi 44 g 2-furaanisu]ionyy1ik loridia, kp 95° 7 mm Hg:ssa; IR (puhdas) 3400 (m), 3120, 1800, 1550 (m), 1450 (S), 1380 (VS), 1210, 1160, 1120 (VS), 1035 (m), 1010 (VS), 913, 882 (S).? 7 70577 13. 7-Furan is u 1 f onyl 11 chloride 90 ml of water, 410 ml of concentrated HCl and 6 8.0 g of 1N-thiuron-2-furan sulfinate were mechanically stirred and cooled to 10-15 ° . Liquid chlorine (12.3 mL, 39.4 g) was added dropwise over 30 minutes. The mixture was stirred for a further 30 minutes at 5 ° C, poured onto ice and extracted with methylene chloride. Evaporation of methylene chloride gave 44 g of 2-furan sulfonyl chloride, bp 95 ° at 7 mm Hg; IR (neat) 3400 (m), 3120, 1800, 1550 (m), 1450 (S), 1380 (VS), 1210, 1160, 1120 (VS), 1035 (m), 1010 (VS), 913, 882 (S).
C. 2-furaanisulfoniamidt 23 g 2-furaanisulfonyylikloridia (138 ml) lisättiin tiputtaen 200 mlraan väkevää NH^OH 0-5°:ssa. Sekoittamisen jälkeen yli yön huoneen lämpötilassa vesi poistettiin tyhjössä ja saostuma pestiin jäävedellä ja kuivattiin. Saalis 14 g 2-furaanisulfoniamidia, sp. 120-122°. (Kirjallisuus sp. 120-122°: JOC 18, 894 (1953)). IR (Nujol) 3250 cm-1, 3100 cm"1, 1600 cm"1 (W), 1550 cm"1, 3190 cm"1, 1140 cm 1, 1120 cm 1, 1055 cm 1, 1005 cm 1, 930 cm 1, 880 cm 1, 843 cm"1 (S).C. 2-Furanesulfonamides 23 g of 2-furansulfonyl chloride (138 mL) were added dropwise to 200 mL of concentrated NH 4 OH at 0-5 °. After stirring overnight at room temperature, the water was removed in vacuo and the precipitate was washed with ice water and dried. Yield 14 g of 2-furansulfonamide, m.p. 120-122 °. (Literature mp 120-122 °: JOC 18, 894 (1953)). IR (Nujol) 3250 cm -1, 3100 cm -1, 1600 cm -1 (W), 1550 cm -1, 3190 cm -1, 1140 cm -1, 1120 cm -1, 1055 cm -1, 1005 cm -1, 930 cm 1, 880 cm -1, 843 cm -1 (S).
D. 2-furaanisulfonyy1i-isosyanaatt iD. 2-Furanesulfonyl isocyanate i
Kuivaa tolueenia (150 ml), 25 ml oksalyylikloridia(295mmo1) ja pientä määrää DABCO (diatsa-bisyklo/l?. 2.27oktaania) kuumennettiin 90°:seen. 10 g 2-furaanisulfoniamidia lisättiin 15 minuutin aikana ja seosta pidettiin 95°:ssa 2 tuntia. Suodattamisen jälkeen liuotin poistettiin tyhjössä antamaan 2,1 g öljyä, joka antoi luonteenomaisen isosyanaatti-absorption infrapunakirjossa (2280 cm 1).Dry toluene (150 mL), 25 mL of oxalyl chloride (295 mL) and a small amount of DABCO (diazabicyclo / 2.2.2 octane) were heated to 90 °. 10 g of 2-furansulfonamide were added over 15 minutes and the mixture was kept at 95 ° for 2 hours. After filtration, the solvent was removed in vacuo to give 2.1 g of an oil which gave a characteristic isocyanate absorption in the infrared spectrum (2280 cm 1).
Esimerkki 9 N-£(9,6-dimetyyli-l,3,5-triatsin-2-yyli)aminokarbonyyli7-2-metyylibentseeni sulfoniamidi 12,3 g:aan 2-amino-4,6-dimetyy1i-1,3,5-triatsiinia 250 ml :ssa kuivaa asetonitriiliä lisättiin sekoittaen 19,7 g 2-metyylibent-seenisulfonyyli-isosyanaattia nopeudella, joka suunniteltiin välttämään reaktioseoksen liiallista kuumenenista. Sekoittamista jatkettiin kunnes haluttu tuote kiteytyi. Tuote poistettiin suodattamalla, pestiin pienellä määrällä etyylieetteriä ja kuivattiin.Example 9 N - ((9,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl) -2-methylbenzenesulfonamide to 12.3 g of 2-amino-4,6-dimethyl-1,3, 5-Triazine in 250 ml of dry acetonitrile was added with stirring 19.7 g of 2-methylbenzenesulfonyl isocyanate at a rate designed to avoid excessive heating of the reaction mixture. Stirring was continued until the desired product crystallized. The product was removed by filtration, washed with a small amount of ethyl ether and dried.
Saatu tuote , N-£( 4,6-dimetyy li -1,3,5-triatsin-2-yyli )aminokarbonyy-li_7-2-metyy] ibentseenisulfoniamidi , suli 141-145°C : ssa .The product obtained, N - (4,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl-7-2-methyl] benzenesulfonamide, melted at 141-145 ° C.
? 8 70577? 8 70577
Esimerkki 10 N-Z'( 4 , 6-dimetyyli-l ,3,5-triatsin-2-yyli)aminokarbonyyli).7-2-klooribentseenisulfonamidi 12,3 g:aan 2-amino-4 , 6-dimetyy 1 i-1,3,5-triats i inia 200 ml:ssa asetöni trii1 ia lisättiin sekoittaen 21,7 g 2-klooribentseenisulfo-nyyli-isosyanaattia. Kaikki jähmeä aine liukeni senjälkeen kun reagoivat aineet lisättiin ja seos haihdutettiin kuiviin. Jähmeää · jäännöstä, hierrettiin etyylieetterissä, ja se eristettiin suodattamalla, jolloin saatiin epäpuhdasta N-£"(4,6-dimetyyli-l,3,5-triatsin-2-yyli) aminokarbonyyli/-2-klooribentseenisulfonamidia, sp. 115-118°. Tämän tuotteen ydinmagneettinen resonanssiabsorptiokirjossa tri-fluorietikkahapossa oli singlettipiikit 2,59 ja 2,9 ppm.Example 10 N-Z '(4,6-Dimethyl-1,3,5-triazin-2-yl) aminocarbonyl) -7-2-chlorobenzenesulfonamide to 12.3 g of 2-amino-4,6-dimethyl -1,3,5-Triazine In 200 ml of triethyl of acetone was added with stirring 21.7 g of 2-chlorobenzenesulfonyl isocyanate. All solids dissolved after the reactants were added and the mixture was evaporated to dryness. The solid residue was triturated with ethyl ether and isolated by filtration to give crude N - [(4,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 115-118 The nuclear magnetic resonance absorption spectrum of this product in trifluoroacetic acid had singlet peaks of 2.59 and 2.9 ppm.
Esimerkki 11 N-/"(4,6-dimetoksi-l,3,5-tri.atsin-2-yyli)aminokarbonyyliZ-2- klooribentseenisulfoniarnidi 15,6 g:aan 2-amino-4,6-dimetoksi-1,3 , 5-triatsiin ia 300 ml:ssa kuivaa metyleenikloridia, joka sisälsi 0,1 g 1 ,4-diatsabisyklo /2 , 2 , 27oktaania , lisättiin 21 g 2-kloor.ibentseen isulfonyyli-isosyanaattia sekoittaen. Seosta sekoitettiin 16 tuntia ja syntyvä jähmeä aine poistettiin suodattamalla. Jähmeän aineen pesun jälkeen 1- klooributaanilla syntynyt tuote, N-/"( 4,6-dimetoksi-l, 3 , 5-triatsin- 2- yyli )-aminokarbonyyli7-2-kloori.bentseenisulfoniamidi , suli 188-189°C:ssa. Infrapuna-absorptLoanalyysi antoi absorptiohuiput 1740 cm , 1630 cm ^ ja 1595 cm ^:ssä, jotka ovat tyypillisiä tämäntyyppisille yhdiste!Ile.Example 11 N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide to 15.6 g of 2-amino-4,6-dimethoxy-1, To 3,5-triazine and 300 ml of dry methylene chloride containing 0.1 g of 1,4-diazabicyclo [2.2.2] octane were added 21 g of 2-chlorobenzene isulfonyl isocyanate with stirring. The solid formed after washing the solid with 1-chlorobutane, N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chloro-benzenesulfonamide, melted 188- 189 ° C. Infrared absorpto analysis gave absorption peaks at 1740 cm, 1630 cm-1 and 1595 cm-2, which are typical of these types of compounds.
Käyttämällä esimerkkien 9-11 menetelmää ekvivalentin määrän kanssa sopivaa aminotriatsiinia ja sopivasti substituoitua sulfonyy-li-isosyanaattia, voidaan valmistaa taulukossa IV esitetyt yhdisteet : 29 70577Using the procedure of Examples 9-11 with an equivalent amount of the appropriate aminotriazine and appropriately substituted sulfonyl isocyanate, the compounds shown in Table IV can be prepared: 29 70577
Taulukko IV-ATable IV-A
<V ^-S02NHCNH-^ N<V ^ -SO2NHCNH- ^ N
<z X_Z_sp .<z X_Z_sp.
CH3 CH3 200-201 CH30 CH30 183-185 CH30 CH3 166-171 CH3CH2CH20 CH30 121-124 CH3S CH30 197-199CH3 CH3 200-201 CH30 CH30 183-185 CH30 CH3 166-171 CH3CH2CH2O CH30 121-124 CH3S CH30 197-199
Taulukko IV-BTable IV-B
XX
QO N—^QO N— ^
SO,,NH-C-NH —\ NSO ,, NH-C-NH - \ N
r2r2
R3 X z sp.°CR3 X z m.p.
CH3 CH30 CH3 158-162 CH3 CH30 CH30 144-147 CH3 CH3OCH2 CH3 147-150 CH3 CH3S CH30 191-193CH3 CH30 CH3 158-162 CH3 CH30 CH30 144-147 CH3 CH3OCH2 CH3 147-150 CH3 CH3S CH30 191-193
Cl CH3 CH3 185-187Cl CH3 CH3 185-187
Cl CH30 CH3 174-178Cl CH30 CH3 174-178
Cl CH30 CH30 188-189Cl CH30 CH30 188-189
Cl CH3OCH3 CH3 142-145Cl CH3OCH3 CH3 142-145
Cl CH3CH20 CH3 117-121Cl CH3CH2O CH3 117-121
Cl CH3CH20 CH30 132-133 F CH30 CH3 168-172 30 70577Cl CH3CH2O CH30 132-133 F CH30 CH3 168-172 30 70577
X z sp. °CX z sp. ° C
F CH30 CH30 169-175 CF3 CH3 CH3 172-174 CF3 CH3 CH30 165-167 CF3 CH30 CH30 171-173 N02 CH3 CH30 178-181 (haj.) N02 CH30 CH30 175-178F CH30 CH30 169-175 CF3 CH3 CH3 172-174 CF3 CH3 CH30 165-167 CF3 CH30 CH30 171-173 NO2 CH3 CH30 178-181 (dec.) NO2 CH30 CH30 175-178
Cl CH3S CH3 160-175Cl CH3S CH3 160-175
Cl Cl CH3 180-182Cl Cl CH3 180-182
Br CH3 CH3 194-196Br CH3 CH3 194-196
Br CH3 CH30 180-181Br CH 3 CH 3 O 180-181
Br CH30 CH30 175-176 F CH3CH20 CH3 168-170 no2 ch3 ch3 105-110 CH3S CH30 CH3 181-184 CH3S CH30 CH30 171-174 CH30 CH3 CH3 193-195 CH30 CH30 CH3 175-179 CH30 CH30 CH30 163-165 C„Hr CH0 CH„ 152-157 C2H5 CH30 CH3 127-132 C2H5 CH30 CH30 152-157 n-C^Hg CH3 CH3 159-162 n-C3H7 CHgO CHgO 149-153 CN CHgO CHgO 130 31 70577Br CH30 CH30 175-176 F CH3CH2O CH3 168-170 no2 ch3 ch3 105-110 CH3S CH30 CH3 181-184 CH3S CH30 CH30 171-174 CH30 CH3 CH3 193-195 CH30 CH30 CH3 175-179 CH30 CH30 CH30 163-165 C Hr CH0 CH „152-157 C2H5 CH30 CH3 127-132 C2H5 CH30 CH30 152-157 nC ^ Hg CH3 CH3 159-162 n-C3H7 CHgO CHgO 149-153 CN CHgO CHgO 130 31 70577
Taulukko iy-C < /SCkNHCNH^ n W \-ςTable iy-C </ SCkNHCNH ^ n W \ -ς
Rg X Z sp.Rg X Z m.p.
Cl CH3 CH3 190-191Cl CH3 CH3 190-191
Cl CH3 CHgO yli 250 CF3 CH3 CH3 158-162 CHg CH3 CH3 184, jähmettyy uudelleen CHg CHgO CHgQ 174, jähmettyy uudelleenCl CH3 CHgO over 250 CF3 CH3 CH3 158-162 CHg CH3 CH3 184, re-solidifies CHg CHgO CHgQ 174, re-solidifies
Taulukko IV-DTable IV-D
,-. O N, -. IS
/Qy~S02NHCNH \/ Qy ~ S02NHCNH \
R4 R3 ZR4 R3 Z
R3 R^ X Z sp.R3 R ^ X Z m.p.
Cl Cl CH3 CH3 130-140Cl Cl CH3 CH3 130-140
Cl Cl CH3 CH30 182-184Cl Cl CH3 CH30 182-184
Cl Cl CHgO CH30 192-193 F Cl CH3 CH3 171-175 F Cl CH3 CH30 190-191 F Cl CH30 CH30 275Cl Cl CHgO CH30 192-193 F Cl CH3 CH3 171-175 F Cl CH3 CH30 190-191 F Cl CH30 CH30 275
Cl CH3 CH3 CH3 188-189Cl CH3 CH3 CH3 188-189
Cl CH3 CH3 CH30 187 R3 R4 X Z sp.Cl CH3 CH3 CH30 187 R3 R4 X Z m.p.
32 7057732 70577
Cl CH3 CH30 CH30 148-151 CH30 Cl CH30 CH30 178 CH30 Cl CH3 CH30 172-174Cl CH3 CH30 CH30 148-151 CH30 Cl CH30 CH30 178 CH30 Cl CH3 CH30 172-174
Taulukko iy-ETable iy-E
/-Γ\ H N Rc-(( )VS0oNHCNH —(\ N/ -Γ \ H N Rc - (() VSO 0 NHCNH - (\ N
b \^/ z N Jb \ ^ / z N J
R3 ^ R3 R5 X Z sp.R3 ^ R3 R5 X Z m.p.
Cl Cl CH30 CH30 182-190 F F CH30 CH30 196-200 CH3 CH30 CH3 CH30 155-156 CH30 CH30 CH30 CH30 218-219 N02 Cl CH30 CH3 163-164Cl Cl CH30 CH30 182-190 F F CH30 CH30 196-200 CH3 CH30 CH3 CH30 155-156 CH30 CH30 CH30 CH30 218-219 NO2 Cl CH30 CH3 163-164
Taulukko IV-FTable IV-F
RKy s j S 0 2 NH CHNf{RKy s j S 0 2 NH CHNf {
\ Z\ Z
R3 R6 X Z sp.R3 R6 X Z m.p.
Cl Cl CH3 CH3 190-192Cl Cl CH3 CH3 190-192
Cl Cl CH3 CH30 186-188Cl Cl CH3 CH30 186-188
Cl Cl CH30 CH30 185-188Cl Cl CH30 CH30 185-188
Cl Cl CH3CH20 CH3 155-159Cl Cl CH3CH2O CH3 155-159
Cl Cl CH3CH20 CH30 147-149Cl Cl CH3CH2O CH30 147-149
Cl CN CH3 CH30 190-193 R3 Rg X Z sp.Cl CN CH3 CH30 190-193 R3 Rg X Z m.p.
70577 33 CH3 CH3 CH3 CHgO 160-163 CH3 CH3 CH30 CH30 169-173 CH30 Cl CH3 CHgO 174-179 CH30 Cl CH30 CH30 165 CHgO Cl CH3CH20 CH3 183-183,5 CH30 F CH30 CH30 201-203 F F CH3 CH3 164-165 F F CHgO CH30 206-20870577 33 CH3 CH3 CH3 CHgO 160-163 CH3 CH3 CH30 CH30 169-173 CH30 Cl CH3 CHgO 174-179 CH30 Cl CH30 CH30 165 CHgO Cl CH3CH20 CH3 183-183.5 CH30 F CH30 CH30 201-203 FF CH3 CH3 164-165 FF CHgO CH30 206-208
Cl CH30 CH3 CH30 176 ci ch3o ch3o ch3o 201Cl CH30 CH3 CH30 176 ci ch3o ch3o ch3o 201
Cl CF3 CH3 CHgO 177-178Cl CF3 CH3 CH2O 177-178
Cl CF3 CH30 CH30 165-167Cl CF3 CH30 CH30 165-167
Cl H CHgO CH3 110-112 ClgCOCT-suolaCl H CHgO CH3 110-112 ClgCOCT salt
Cl H CH30 CH3 öljy (CH3CH2CH2CH2)4N+-suolaCl H CH 3 O 3 CH 3 oil (CH 3 CH 2 CH 2 CH 2) 4 N + salt
Cl H CH30 CH3 öljy £CH3(CH2)674N+-suolaCl H CH 3 O 3 CH 3 oil ε CH 3 (CH 2) 674N + salt
Cl N02 CH3 CH3 142-144Cl NO 2 CH 3 CH 3 142-144
Cl N02 CH30 CH30 168-174 CH30 CH3 CH30 CH30 210-213 F CH3 CH3 CH3 180-182 F CH3 CH3 CHgO 185-186 F CH3 CH30 CHgO 191-192 CH3 F CH3 CH3 201-205 CH3 F CH30 CH30 183-184 CH3 CH3S02 CH3 CH3 181-184(d) CH3S Cl CH3 CH30 95-100 CH3S Cl CH30 CH30 190-194 CH3 N02 CH3 CHgO 190-191 CH3 N02 CH3 CHgO 190-230 (haj.) Na-suola R3 Kg X Z sp.Cl NO2 CH30 CH30 168-174 CH30 CH3 CH30 CH30 210-213 F CH3 CH3 CH3 180-182 F CH3 CH3 CHgO 185-186 F CH3 CH30 CHgO 191-192 CH3 F CH3 CH3 201-205 CH3 F CH30 CH30 183-184 CH3 CH 3 SO 2 CH 3 CH 3 181-184 (d) CH 3 S Cl CH 3 CH 3 O 95-100 CH 3 S Cl CH 3 CH 3 O 190-194 CH 3 NO 2 CH 3 CH 2 O 190-191 CH 3 NO 2 CH 3 CH 2 O 190-230 (dec.) Na salt R 3 Kg XZ m.p.
34 70577 CH3 N02 CH30 CH30 142-145 CH3 (CH3)2CH CH3 CH3 167 ch3 cch3)2ch ch3 ch3o 115 CH3 (CH3)2CH CH30 CH30 135 CH3CH20 Cl CH3 CH30 179-181 CH3CH20 CH3CH20 CH3 CH3 134-136 CH , CH _ 0 CH,CH„0 CH,0 CHo0 187-188 CH3 Cl CH3 CH3 189-191 CH3 Cl CH3 CH30 172-174 CH, Cl CH,0 CH 0 182-18434 70577 CH3 NO2 CH30 CH30 142-145 CH3 (CH3) 2CH CH3 CH3 167 ch3 cch3) 2ch ch3 ch3o 115 CH3 (CH3) 2CH CH30 CH30 135 CH3CH2O Cl CH3 CH30 179-181 CH3CH2O3 CH3CH2O CH3 CH3 134-136 CH, CH _ 0 CH, CH „0 CH, 0 CHo0 187-188 CH3 Cl CH3 CH3 189-191 CH3 Cl CH3 CH30 172-174 CH, Cl CH, 0 CH 0 182-184
ό ό Oό ό O
Br Br CH3 CHg 204-205Br Br CH3 CH2 204-205
Br Br CH3 CHgO 178-180Br Br CH 3 CH 2 O 178-180
Br Br CH30 CHgO yli 275 CH30 CH30 CH3 CH3 144-150 CH30 CH30 CH3 CH30 187-205 (haj.) CH30 CH30 CH3 CH30 öljy (CH3CH2CH CH2)^Ν+- suola CH30 CH,0 CH30 CH30 187-188 CH30 CH30 CH3CH20 CH3 96-100 CH30 CH30 CH3CH20 CH30 138-141 (CH3)2CH (CH3)2CH CH30 CH30 123-128 CH3CH20 Cl CH30 CH30 174-178 35 70577Br Br CH30 CHgO over 275 CH30 CH30 CH3 CH3 144-150 CH30 CH30 CH3 CH30 187-205 (dec.) CH30 CH30 CH3 CH30 oil (CH3CH2CH CH2) ^ Ν + - salt CH30 CH, 0 CH30 CH30 187-188 CH30 CH30 CH3CH2O CH3 96-100 CH30 CH30 CH3CH2O CH30 138-141 (CH3) 2CH (CH3) 2CH CH30 CH30 123-128 CH3CH2O Cl CH30 CH30 174-178 35 70577
Taulukko IV-GTable IV-G
/—/7 0 N/ - / 7 0 N
(Cj)-S0oNHCNH ~\ N \^/ 2 R3 R3 R7 X Z sp.(Cj) -SO0NHCNH ~ \ N \ ^ / 2 R3 R3 R7 X Z m.p.
Cl Cl CH3 CH3 142-158Cl Cl CH3 CH3 142-158
Cl Cl CH3 CH30 203-206Cl Cl CH3 CH30 203-206
Cl Cl CH30 CH30 205-208Cl Cl CH30 CH30 205-208
Cl CH3 CH3 CH30 171-172Cl CH3 CH3 CH30 171-172
Cl CH3 CH30 CH30 173-176 F F CH3 CH3 192-193 F F CH3 CH30 213-215 F F CHgO CH30 275Cl CH3 CH30 CH30 173-176 F F CH3 CH3 192-193 F F CH3 CH30 213-215 F F CHgO CH30 275
Cl CH30 CH30 CH30 174-178Cl CH30 CH30 CH30 174-178
Taulukko IV-H 6)—\ 2 NTable IV-H 6) - \ 2 N
/QVS02nh^nh N/ QVS02nh ^ nh N
>_/ N =<> _ / N = <
r4 Zr4 Z
R4 R6 X Z sp.R4 R6 X Z m.p.
Cl Cl CH3 CH3 210-213Cl Cl CH3 CH3 210-213
Cl Cl CH30 CH30 207 3 6 70577Cl Cl CH30 CH30 207 3 6 70577
Taulukko XV"1 /ΤλΥ A /N=^ RS-<O/ 302NHCNH-<n ^ R4 z K4 R5 X Z sp.Table XV "1 / ΤλΥ A / N = ^ RS- <O / 302NHCNH- <n ^ R4 z K4 R5 X Z m.p.
Cl Cl CH3 CH3 194-195Cl Cl CH3 CH3 194-195
Cl Cl CH3 CH30 188-190Cl Cl CH3 CH30 188-190
Cl Cl CH30 CH30 280 N02 CH30 CH3 CH30 182-185Cl Cl CH30 CH30 280 NO2 CH30 CH3 CH30 182-185
Taulukko IV-J 0Table IV-J 0
R^VfYVsO^NHCNH -4 NR 2 VfYV 5 O 2 NHCNH -4 N
Ί R3 R3 R4 R5 X z sp.Ί R3 R3 R4 R5 X z sp.
Cl Cl Cl CH3 CH3 178-184Cl Cl Cl CH3 CH3 178-184
Cl Cl Cl CH3 CH30 169-171Cl Cl Cl CH3 CH30 169-171
Cl Cl Cl CH30 CH30 175-178 37 70577Cl Cl Cl CH30 CH30 175-178 37 70577
Taulukko IV-KTable IV-K
/P^V-SO NHCNH -ζ \ R3 r3 \ rg X Z sp./ P ^ V-SO NHCNH -ζ \ R3 r3 \ rg X Z sp.
CH, CH3 N02 CH3 CH30 182-1314 (haj.) CH CH N02 CH3 CH3 196-197 (haj.)CH, CH3 NO2 CH3 CH30 182-1314 (dec.) CH CH NO2 CH3 CH3 196-197 (dec.)
Taulukko IV-LTable IV-L
/-\7 0 Ν^Χ <Oso2NHCNH -(v^/ - \ 7 0 Ν ^ Χ <Oso2NHCNH - (v ^
R44 ' R3 ZR44 'R3 Z
r3 r4 r7 X Z sp.r3 r4 r7 X Z sp.
CH3 Cl Cl CH3 CH3 168-170 CH3 Cl Cl CH30 CH3 176-178 CH30 Cl Cl CH30 CH30 173-175CH3 Cl Cl CH3 CH3 168-170 CH3 Cl Cl CH30 CH3 176-178 CH30 Cl Cl CH30 CH30 173-175
Taulukko IV-MTable IV-M
« /N ^«/ N ^
R. -(( ))-SO,NHCNH NR. - (()) - SO, NHCNH N
5 urv 2 ' n R3 ^ R3 R, Rg X Z sp.5 urv 2 'n R3 ^ R3 R, Rg X Z m.p.
Cl Cl Cl CH3 CH3 184-186Cl Cl Cl CH3 CH3 184-186
Cl Cl Cl CH3 CH30 169-171Cl Cl Cl CH3 CH30 169-171
Cl Cl Cl CH30 CH30 165-168 CH30 Cl CH30 CH30 CH30 195 38 70577Cl Cl Cl CH30 CH30 165-168 CH30 Cl CH30 CH30 CH30 195 38 70577
Taulukko IV-N R XTable IV-N R X
Rr-(0 VsO^NHCNH ~L NRr- (O VsO 2 NHCNH-L N
5uk( 2 Λ Λ, R3 z5uk (2 Λ Λ, R3 z
Rg Rg Ry X Z sp.Rg Rg Ry X Z sp.
CH3 CH3 CH3 CH3 CH3 205-207 CH3 CH3 CH3 CH3 CH30 177-186 CH3 CH3 CH3 CH30 CH30 160-167 F F F CH3 CH3 163-169 F F F CH3 CH30 152-155 F F F CH30 CH30 194-196CH3 CH3 CH3 CH3 CH3 205-207 CH3 CH3 CH3 CH3 CH30 177-186 CH3 CH3 CH3 CH30 CH30 160-167 F F F CH3 CH3 163-169 F F F CH3 CH30 152-155 F F F CH30 CH30 194-196
Cl Cl Cl CH3 CH3 188-190Cl Cl Cl CH3 CH3 188-190
Cl Cl Cl CH3 CH O 159-161Cl Cl Cl CH3 CH O 159-161
Cl Cl Cl CH30 CH30 166-168Cl Cl Cl CH30 CH30 166-168
Taulukko IV-0 Rg \ /^7 O j\j <Q>-so2nhcnh^ )Table IV-0 Rg \ / ^ 7 O j \ j <Q> -so2nhcnh ^)
K*3 ZK * 3 Z
R3 R4 4 Rg Ry X Z sp.R3 R4 4 Rg Ry X Z m.p.
CHg CHg CH3 CH3 CH3 CH3 200-205 CH3 CH3 CHg CHg CHg CHgO 195-197 CH3 CH3 CHg CH3 CHgO CHgO 185-189CHg CHg CH3 CH3 CH3 CH3 200-205 CH3 CH3 CHg CHg CHg CHgO 195-197 CH3 CH3 CHg CH3 CHgO CHgO 185-189
Cl Cl Cl Cl CHg CHgO 187Cl Cl Cl Cl CHg CHgO 187
Cl Cl Cl Cl CH30 CHgO yli 250 39 70577Cl Cl Cl Cl CH30 CHgO over 250 39 70577
Esimerkki 12 4-metoksi-6-metyyli-l, 3,5-trj.atsin-2-yyli)aminokarbonyy-117-2-tiofeenisulfoniamidiExample 12 4-Methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl-117-2-thiophenesulfonamide
Suspensioon, jossa oli 14,0 g 2-amino-4-metoksi-6-metyyli- 1,3,5-triatsiinia 300 ml:ssa asetonitriiliä, lisättiin tiputtaen 19 g tiofeeni-2-sulfonyyli-isosyanaattia. 6-tuntisen sekoittamisen jälkeen seos suodatettiin antamaan haluttu jähmeä tuote, joka suli 182-184°C:ssa.To a suspension of 14.0 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 300 ml of acetonitrile was added dropwise 19 g of thiophene-2-sulfonyl isocyanate. After stirring for 6 hours, the mixture was filtered to give the desired solid product, melting at 182-184 ° C.
Käyttämällä esimerkin 12 menetelmä ekvivalentteina määrillä sopivaa amino-1,3,5-triatsiini-johdannaisia ja sulfonyyli-isosya-naattia voidaan valmistaa taulukon V yhdisteet.Using the method of Example 12 in equivalents with amounts of the appropriate amino-1,3,5-triazine derivatives and sulfonyl isocyanate, the compounds of Table V can be prepared.
Taulukko V-ATable V-A
SS
--tS0oNH-C-NH -χ N--tSO 0 NH-C-NH-χ N
I il 2 'n-=< ^ 8ΛθI il 2 'n - = <^ 8Λθ
Rg R10 X Z sp* C1 Cl CH3 CH3 127-133 C1 Cl CH3 CH30 165-171 C1 Cl CHgO CHgO 181-184Rg R10 X Z sp * C1 Cl CH3 CH3 127-133 C1 Cl CH3 CH30 165-171 C1 Cl CHgO CHgO 181-184
Taulukko V-BTable V-B
Oso2jnh7 t R8 V \ ^ E X z Q sp.Oso2jnh7 t R8 V \ ^ E X z Q sp.
a8 H CH3 CH3 s 174-176 H CH3 CHgO S 182-184 H CHgO CHgO S 191-192 CH CH3 CHgO S 159-162 4 0 70577a8 H CH3 CH3 s 174-176 H CH3 CHgO S 182-184 H CHgO CHgO S 191-192 CH CH3 CHgO S 159-162 4 0 70577
Rg X Z Q sp.Rg X Z Q sp.
Cl CHg CH3 S 192-195Cl CHg CH3 S 192-195
Cl CHg 0 CH30 S 193-195 H CH3CH2 CH3 S 132-138 H CH^S CH0 S 223-225 ö 3Cl CHg 0 CH30 S 193-195 H CH3CH2 CH3 S 132-138 H CH ^ S CH0 S 223-225 ö 3
Esimerkki 13 N-ZK4,6-dimetoksi-l,3,5-triatsin-2-yyli)aminokarbonyyli7-l- naftaleenisulfoniamidiExample 13 N-ZK 4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl-1-naphthalenesulfonamide
Suspensioon, jossa oli 16 g 2-amino-4,6-dimetoksi-l,3,5-tri-atsiinia 400 ml:ssa asetonitriiliä, lisättiin sekoittaen 23,3 g 1-naftaleenisulfonyyli-isosyanaattia pisaroittain. Seosta sekoitettiin 14 tuntia ja saatu jähmeä tuote poistettiin suodattamalla.To a stirred suspension of 16 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 400 ml of acetonitrile was added dropwise 23.3 g of 1-naphthalenesulfonyl isocyanate. The mixture was stirred for 14 hours and the resulting solid product was removed by filtration.
Pesun jälkeen etyylieetterillä tuote suli 171-172°C:ssa.After washing with ethyl ether, the product melted at 171-172 ° C.
Käyttäen esimerkin 13 menetelmää ja substituoiden ekvivalentteja määriä sopivaa amini-1,3,5-triatsiinia ja sulfonyyli-isosyanaattia voidaan valmistaa seuraavat taulukon VI yhdisteet:Using the procedure of Example 13 and substituting equivalent amounts of the appropriate Amine 1,3,5-triazine and sulfonyl isocyanate, the following compounds of Table VI can be prepared:
Taulukko VITable VI
0 n K /0 n K /
S0,.NHCNH“V NS0, .NHCNH “V N
KK
X Z sp.X Z sp.
CH3 CH3 179-183 CH3 CHg0 186-188 CHgO CHgO 171-172CH3 CH3 179-183 CH3 CHg0 186-188 CHgO CHgO 171-172
Esimerkki 14 Ν-ϋ 4,6-dimetoksi-l,3,5-triatsin-2-yyli)aminotioksometyyli7-bentseenisulfoniamidiExample 14 N- (4,6-Dimethoxy-1,3,5-triazin-2-yl) aminothioxomethyl-7-benzenesulfonamide
Seosta, joka sisälsi 20 g bentseenisulfonyyli-isotiosyanaattia, 15,6 g 2-amino-4,6-dimetoksi-l,3,5-tiratsiinia, 250 ml asetonitriiliä ja katalyyttisen määrän dibutyylitinadilauraattia, sekoitettiin 24 tuntia. Suodattamisen jälkeen reagoimattoman triatsiinin poistamiseksi, saatiin haihduttamalla asetonitriili kumimainen jäännös.A mixture of 20 g of benzenesulfonyl isothiocyanate, 15.6 g of 2-amino-4,6-dimethoxy-1,3,5-thiazine, 250 ml of acetonitrile and a catalytic amount of dibutyltin dilaurate was stirred for 24 hours. After filtration to remove unreacted triazine, a rubbery residue was obtained by evaporation of acetonitrile.
70577 4170577 41
Hiertämällä tätä ainetta etyylieetterin kanssa, saostui haluttu yhdiste, joka eristettiin suodattamalla ja joka suli 148-150°C:ssa.Trituration of this material with ethyl ether precipitated the desired compound, which was isolated by filtration and melted at 148-150 ° C.
Käyttäen esimerkin 6 menetelmää ekvivalentin määrän kanssa sopivaa sulfonyyli-isotiosyanaattia ja aminotriatsiinia, voidaan valmistaa taulukon VII yhdisteet.Using the procedure of Example 6 with an equivalent amount of the appropriate sulfonyl isothiocyanate and aminotriazine, the compounds of Table VII can be prepared.
Taulukko VIITable VII
r1so2nh?nhr2r1so2nh? NHR 2
Ra R2 Sp’ CN « 9CHo kaasun ke- /, hit^s 118-\ /- \ N 130 C:ssa, sp.Ra R2 Sp 'CN «9CHo gas at <118 ° C, m.p.
\ — / N ^ 2 5 0 ΧΗ3 JT\ \ Γ /,N Λ 182-185 H -f * N _/ ch^och3 ( >- _3 142-144 ^“4 /* CHo0 v N _/ )Τ\ ~^ch3 <7 7- N~d0CH, \_/ Λ 188-190 (haj.)\ - / N ^ 2 5 0 ΧΗ3 JT \ \ Γ /, N Λ 182-185 H -f * N _ / ch ^ och3 (> - _3 142-144 ^ “4 / * CHo0 v N _ /) Τ \ ~ ^ ch3 <7 7- N ~ d0CH, \ _ / Λ 188-190 (dec.)
Vh, Λ /NVh, Λ / N
3 N =/ ^CH33 N = / ^ CH3
Valmistemuotojaformulations
Kaavan I yhdisteiden hyödyllisiä valmistemuotoja voidaan valmistaa tavanomaisella tavalla. Ne käsittävät pölyjä, rakeita, pillereitä, liuoksia, suspensioita, emulsioita, kostuvia jauheita, emulgoituvia väkevöitteitä jne. Useita näistä voidaan käyttää suoraan. Suihkutettavat valmistemuodot voidaan laimentaa sopivassa väliaineessa ja käyttää suihkutustilavuuksissa muutamista litroista moniin satoihin litroihin hehtaaria kohti. Erittäin vahvoja yhdistelmiä käytetään ensisijaisesti välituotteina lisämuodostusta varten.Useful formulations of the compounds of formula I may be prepared in a conventional manner. They include dusts, granules, pills, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, etc. Several of these can be used directly. The formulations to be sprayed can be diluted in a suitable medium and used in spray volumes from a few liters to many hundreds of liters per hectare. Very strong combinations are used primarily as intermediates for further formation.
4 2 705774 2 70577
Valmistemuodot sisältävät yleisesti n. 0,1-99 paino-% vaikuttavaa ainetta (aineita) ja ainakin toista seuraavista: a) n. 0,1-20 % pinta-aktiivista ainetta (aineita) ja b) n. 1-99,9 % jähmeätä tai nestemäistä jatkoainetta (aineita). Erityisesti ne sisältävät näitä aineosia seuraavissa likimääräisissä suhteissa: 4 3 70577 eThe formulations generally contain about 0.1 to 99% by weight of active ingredient (s) and at least one of the following: a) about 0.1-20% of surfactant (s) and b) about 1-99.9% by weight. % solid or liquid extender (s). In particular, they contain these ingredients in the following approximate proportions: 4 3 70577 e
CDCD
c •rl /—>c • rl / ->
> -M> -M
•H 0)• H 0)
•H CD• H CD
μ c o in o tnμ c o in o tn
·* '2 HH CM LH H CM· * '2 HH CM LH H CM
lp (Ti ,1 tilllp (Ti, 1 till
^ HO H O O O^ HO H O O O
-μ cd c c-μ cd c c
•H »H• H »H
cl, rd a) ^ c ^ _ •H μ -zf- m -zt o> o\ ocl, rd a) ^ c ^ _ • H μ -zf- m -zt o> o \ o
ifl a) t— ΟΛ dj CX\ θ'» Hifl a) t— ΟΛ dj CX \ θ '»H
O CD II I I I IO CD II I I I I
mc o o o o m o μ -h -M- -zt c- <d td H ^ cmc o o o o m o μ -h -M- -zt c- <d td H ^ c
M CDM CD
n c oo ominen m -Htt n in mcMChOv jn c oo characteristic m -Htt n in mcMChOv j
> > “ I I I I I I>> “I I I I I I
n '1 2 o m o h h o 5 μ c H o M M -H ~ 3 < td tdn '1 2 o m o h h o 5 μ c H o M M -H ~ 3 <td td
rH CrH C
3 -H3 -H
id 3 h μ> μid 3 h μ> μ
CDCD
33
μ rHμ rH
CD c co id x id ο λ; 3 3 h 6 μ rH :td μ 6CD c co id x id ο λ; 3 3 h 6 μ rH: td μ 6
·> CD rH·> CD rH
μ cd <u ο μ μ μ •η μ ο to (0 ·γΗ ·γΗ Ή Η ¢) CD Ό 3 > C Λ E cd cd μ >ι μ α> ,* α< ·η cd «ο co ^ μ CD ^ > 3 CD :id ,c μ ω μ >μ cd <u ο μ μ μ • η μ ο to (0 · γΗ · γΗ Ή Η ¢) CD Ό 3> C Λ E cd cd μ> ι μ α>, * α <· η cd «ο co ^ μ CD ^> 3 CD: id, c μ ω μ>
3 Ο μ Η CD3 Ο μ Η CD
id ·η <d μ ·η ACid · η <d μ · η AC
•π 10 > CD ft :rd q 3 ίο > μ cd μ -μ id id cx ·η ο *r-> c > co ο μ ·η 3 3 Μ ·Η μ ;id μ to μ λ μ <d μ co >, 3 ·η >, id μ Ο ·μ Ε ιο μ Μ ·Η X μ CD CD :0 Id q• π 10> CD ft: rd q 3 ίο> μ cd μ -μ id id cx · η ο * r-> c> co ο μ · η 3 3 Μ · Η μ; id μ to μ λ μ <d μ co>, 3 · η>, id μ Ο · μ Ε ιο μ Μ · Η X μ CD CD: 0 Id q
:θ ^ > Oh « W: θ ^> Oh «W
^ 70577^ 70577
Aktiivista aineosaa voi tietenkin olla läsnä sekä pienempiä että suurempia määriä riippuen aiotusta käytöstä ja yhdisteen fysikaalisista ominaisuuksista. Pinta-aktiivisen aineen suuremmat suhteet aktiiviseen aineosaan ovat joskus haluttuja ja niihin päästään yhdistämällä valmistemuotoon tai säiliössä sekoittamalla.Of course, the active ingredient may be present in both smaller and larger amounts depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desired and can be achieved by combining the formulation or by mixing in a container.
Tyypillisiä jähmeitä jatkoaineita on kuvattu Watkins et ai'in käsikirjassa "Handbook of Insecticide Dust Diluents and Carriers", 2. painos, Dorland Books. Caldwell, New Jersey. Imukykyisemmät jatko-aineet ovat edullisia kostuville jauheille ja tiiviimmät pölyille. Tyypillisiä nestemäisiä laimentimia ja liuottimia on kuvannut Marsden teoksessa "Sovents Guide", 2. painos, Interscience, New York, 1950, Alle 0,1 %:n liukoisuus on edullinen suspensio-väkevöit-teille; 1iuosväkevöitteet ovat edullisesti kestäviä faasin erottumista vastaan 0°C:ssa. Julkaisuissa "McCutcheon's Detergents and Emulsidiers Annual", Mc Publishing Corp., Ridgewood, New Jersey, sekä Sisely'n ja Wood'in "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York 1964, luetellaan pinta-aktiivisia aineita ja suositeltavia käyttöjä. Kaikki valmistemuodot voivat > sisältää pieniä määriä lisäaineita vähentämään vaahtoa, paakkuntu-mista, syöpymistä, mikrobiologista kasvua jne.Typical solid extenders are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Edition, Dorland Books. Caldwell, New Jersey. More absorbent extenders are preferred for wettable powders and tighter for dusts. Typical liquid diluents and solvents are described by Marsden in "Sovents Guide", 2nd Edition, Interscience, New York, 1950, A solubility of less than 0.1% is preferred for suspension concentrates; The solution concentrates are preferably resistant to phase separation at 0 ° C. McCutcheon's Detergents and Emulsidiers Annual, Mc Publishing Corp., Ridgewood, New Jersey, and Sisely and Wood's Encyclopedia of Surface Active Agents, Chemical Publishing Co., Inc., New York 1964, list surface active substances and recommended uses. All formulations may> contain small amounts of additives to reduce foam, agglomeration, corrosion, microbiological growth, etc.
Menetelmät tällaisten yhdistelmien valmistamiseksi ovat hyvin tunnettuja. Liuoksia valmistetaan yksinkertaisesti sekoittamalla aineosat. Hienoja jähmeitä yhdistelmiä tehdään sekoittamalla ja tavallisesti jauhamalla, kuten vasramyllyssä tai neste-energiamyl-lyssä. Suspensiot valmistetaan märkäjauhatuksella (ks. esimerkiksi Littler, U.S. patentti 3.060.084). *Methods for preparing such combinations are well known. Solutions are prepared simply by mixing the ingredients. Fine solid combinations are made by mixing and usually grinding, such as in a hammer mill or liquid energy mill. Suspensions are prepared by wet milling (see, e.g., Littler, U.S. Patent 3,060,084). *
Rakeita ja pillereitä voidaan tehdä ruiskuttamalla aktiivinen aine etukäteen muodostetuille raekantimille tai agglomeroimismene-telmillä. Ks. J.E. Browning, "Agglomeration", Chemical Engineering, ; joulukuu 4, 1967 s. 147-, ja "perry's Chemical Engineer's Handbook", ; 4. painos, McGraw-Hill, New York, 1963, s. 8-59. jGranules and pills can be made by spraying the active ingredient onto preformed granular carriers or by agglomeration methods. See. JE Browning, Agglomeration, Chemical Engineering,; December 4, 1967, pp. 147-, and "Perry's Chemical Engineer's Handbook,"; 4th edition, McGraw-Hill, New York, 1963, pp. 8-59. j
Lisätietojen saamiseksi, jotka koskevat valmitemuodon lajia, ks, esimerkiksi: H.M. Loux, U.S. patentti 3.235.361, 15.2.1966, sarake 6, riviltä 16 sarakkeeseen 7, riville 19 ja esimerkit 10-41.For more information on the type of formulation, see, for example: H.M. Loux, U.S.A. Patent 3,235,361, February 15, 1966, column 6, line 16 to column 7, line 19, and Examples 10-41.
R.W. Luckenbaugh, U.S. patentti 3.309.192, 14.3.1967, sarakkeen 5, riviltä 43 sarakkeen 7 riville 62 ja esimerkit 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 ja 169-182.R. W. Luckenbaugh, U.S.A. Patent 3,309,192, March 14, 1967, from column 5, line 43 to column 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182.
i l { ^ 70577 H. Gysin ja K. Knusli. , U.3. pat ent L i 2 . 89 1.855 , 2 3.6.1959 , sarakkeen 3 riviltä 66 sarakkeen 5 riville 17 sekä esimerkit 1-4.i l {^ 70577 H. Gysin and K. Knusli. , U.3. pat ent L i 2. 89 1,855, 2 June 3, 1959, from row 3 of column 66 to row 17 of column 5, and Examples 1-4.
G.C. Klingman, "Weed Control as a Science", John Viley &G.C. Klingman, "Weed Control as a Science", John Viley &
Sons, Inc., New York, 1961, s. 81-96.Sons, Inc., New York, 1961, pp. 81-96.
J.D. Fryer ja S.A. Evans, "Weed Control Handbook", 5. painos, Blackwell Scientific Publications, Oxford, 1968, s. 101-103.J.D. Fryer and S.A. Evans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
Seuraavissa esimerkeissä kaikki osat on laskettu painosta ellei toisin ole esitetty.In the following examples, all parts are by weight unless otherwise indicated.
Esimerkki 15 Kostuva jauhe N-Z(4,6-dimetyylipyrimidin-2-yyli)aminokarbonyyli7-bentseenisulfoniamidia 80 % natriumalkyylinaftaleenisulfonaa11ia 2 % natriumligniinisulfonaattia 2 % synteettistä amorfista piidioksidia 3 % kaoliniittia 13 %Example 15 Wettable powder N-Z (4,6-dimethylpyrimidin-2-yl) aminocarbonyl-7-benzenesulfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium lignin sulfonate 2% synthetic amorphous silica 3% kaolinite 13%
Kaikki aineosat sekoitetaan, jauhetaan vasaramyllyssä kunnes kaikki jähmeät aineet ovat kooltaan oleellisesti alle 50 mikronin ja sekoitetaan sitten uudelleen.All ingredients are mixed, ground in a hammer mill until all solids are substantially less than 50 microns in size, and then mixed again.
Esimerkki 16 Kostuva jauhe N-Z”(4-inetoksi-6-metyylipyrimidin-2-yyli)-amino-karbonyyli/-2-kloor i- 5-me toks i be nt.se eni su lfoni amidia 50 % natriumalkyylinaftaleenisulfonaattia 2 % vähäviskoosista metyyliselluloosaa 2 % piimaata 46 %Example 16 Wetting powder NZ ”(4-ethoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzene sulfonamide 50% sodium alkylnaphthalenesulfonate 2% low viscosity methylcellulose 2% milk 46%
Aineosat sekoitetaan, jauhetaan vasaramyllyssä karkeasti ja sitten ilmamyllyssä antamaan aktiivisia hiukkasia, joiden läpimitta on oleellisesti alle 10 mikronia. Tuote sekoitetaan uudelleen ennen pakkaami s ta.The ingredients are mixed, coarsely ground in a hammer mill and then in an air mill to give active particles substantially less than 10 microns in diameter. The product is mixed again before packaging.
Esimerkki 17 RakeetExample 17 Granules
Esimerkin 16 kostuvaa jauhetta 5 % attapulgiitti-rakeita 95 % (U.S.S-seulamitta 20-40 mesh; 0,84-0,42 mm)Example 16 wettable powder 5% attapulgite granules 95% (U.S.S sieve size 20-40 mesh; 0.84-0.42 mm)
Kostuvan jauheen liete, joka sisältää n. 25 % kuiva-ainetta ruiskutetaan attapulgiitti-rakeiden pinnalle kaksoiskartiosekoitti-messa. Rakeet kuivataan ja pakataan.A wettable powder slurry containing about 25% dry matter is sprayed onto the surface of the attapulgite granules in a twin cone mixer. The granules are dried and packaged.
τ 70577τ 70577
Esimerkk i 18Example 18
Suu lake pur is te t:lu pilleri N-Z"(4-metoks i-6-metyylipyrimidin-2-yyli) amino-karbonyyli7-2-klooribentseenisulfoniamidia 25 % vedetöntä natriumsulfaattia 10 % raakaa kaisiumligniinisulfonaattia 5 1 natriumalkyy1inaftaleenisulfonaattia 1 % kalsium/magnesiumbentoniittia 59 %Oral suppository pill N-Z "(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide 25% anhydrous sodium sulfate 10% crude calcium lignin sulfonate 5 L sodium alkylnaphthalene sulfonate
Aineosat sekoitetaan, jauhetaan vasaramyllyssä ja kostutetaan sitten n. 12 %:lla vettä. Seos suulakepuristetaan n. 3 mm:n läpimittaisina sylintereinä, jotka leikataan antamaan n. 3 mm:n pituisia pillereitä. Näitä voidaan käyttää suoraan kuivaamisen jälkeen tai kuivatut pillerit voidaan muskata läpäisemään U.S.A. no. 20 seula (aukot 0,84 mm). Rakeet, jotka pysyvät U.S.A. no. 40 seulalla (aukot 0,42 mm) pakataan käyttöä varten ja hienommat palautetaan. Esimerkki 19 01jysuspens io N-Z~(4,6-dimetoksipyrimidin-2-yyli)-arnino-karbonyyli/-2,5-diklooribentseenisulfoniamidia 25 % polyoksieteenisorbitoliheksaoleaattia 5 % erittäin alifaattista hiilivetyöljyä 70 %The ingredients are mixed, ground in a hammer mill and then moistened with about 12% water. The mixture is extruded into cylinders about 3 mm in diameter, which are cut to give pills about 3 mm long. These can be used directly after drying or the dried pills can be muscled to pass U.S.A. Well. 20 sieve (openings 0.84 mm). Granules that remain in U.S.A. Well. 40 sieves (openings 0.42 mm) are packaged for use and the finer ones are returned. Example 19 01suspension N-Z- (4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide 25% polyoxyethylene sorbitol hexoleate 5% highly aliphatic hydrocarbon oil 70%
Aineosia jauhetaan yhdessä hiekkamyllyssä kunnes kiinteiden hiukkasten läpimitta on pienentynyt alle n. 5 mikronin. Saatu suspensio voidaan käyttää suoraan, mutta edullisesti senjälkeen kun sitä on laimennettu öljyillä tai. se on emulgoitu veteen.The ingredients are ground in one sand mill until the diameter of the solid particles has decreased to less than about 5 microns. The resulting suspension can be used directly, but preferably after dilution with oils or. it is emulsified in water.
Esimerkki 20 Kostuva jauhe N - C{ 4,6-dimetyy 1 ipyrim i d i n - 2 - yy li ) am.i.no-karbonyyli.7-2 ,5-diklooribentseenisulfoniamidia 20 % natriumalkyylinaftaleenisulfonaattia 4 % natriumlign iinisulfonaattia 4 -% vähäviskoosis ta metyyliselluloosaa 3 % attapulgiittia 69 %Example 20 Wettable Powder N - C (4,6-Dimethylpyrimidin-2-yl) amino-carbonyl] -2,5-dichlorobenzenesulfonamide 20% Sodium Alkylnaphthalenesulfonate 4% Sodium Lignin Sulfonate 4% Low Viscosity Methylcellulose 3% attapulgitis 69%
Aineosat sekoitetaan perusteellisesti. Jauhamisen jälkeen va- saramyllyssä hiukkasten saamiseksi, jotka ovat pääasiallisesti kaik ki läpimitaltaan alle 100 mikronia, aine sekoitetaan uudelleen ja v/ 70577 ja seulotaan U.S.S. no. 50 seulan (aukko 0,3 mm) läpi ja pakataan. Esimerkki 2 1The ingredients are mixed thoroughly. After grinding in a hammer mill to obtain particles substantially all less than 100 microns in diameter, the material is remixed and v / 70577 and screened by U.S.S. Well. Through a 50 sieve (aperture 0.3 mm) and packed. Example 2 1
Rakeet, joilla on pieni väkevyys N-/X 4-metoks i-6-metyyli pyrimidin-2-yyli)amino- karbonyyli.7-2-metyylibentseenisulfon i amidia 1 % N,N-dimetyyliformamidia 9 o attapulgi i tt i-rake.ita 90 % (U.S.S. seulakoko 20-40 mesh).Low concentration granules N- (X (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl) -2-methylbenzenesulfonamide 1% N, N-dimethylformamide 9 o attapulgi i tt i-granule .ita 90% (USS screen size 20-40 mesh).
Aktiivinen aineosa liuotetaan liuottimeen ja liuos suihkutetaan rakeille, joista pöly on poistettu, kaksoiskartiosekoittimessa. Senjälkeen kun liuoksen ruiskutus on loppuunsuoritettu, annetaan sekoittimen pyöriä lyhyen aikaa ja sitten rakeet pakataan.The active ingredient is dissolved in a solvent and the solution is sprayed onto the dedusted granules in a twin cone mixer. After the injection of the solution is completed, the stirrer is allowed to run for a short time and then the granules are packed.
Esimerkki 22 Vesipitoinen suspensio N-ZT( 4,6 - dime tyy li puri mi di n-2-yyli) amino-karbonyyli_7-bentseenisulfoniamidia 40 % polyakryy1ihappopaksunninta 0,3 %Example 22 Aqueous suspension of N-ZT (4,6-dimethylpuridin-2-yl) aminocarbonyl-7-benzenesulfonamide 40% polyacrylic acid thickener 0.3%
dodekyyli fenolipolyeteeniglykolieetteri a 0,5 Edodecyl phenol polyethylene glycol ether a 0.5 E
dinatriumfosfaattia 1,0 % mononatriumfosfaattia 0,5 % polyvinyyli alkoholia 1,0 % vettä 56,7 %disodium phosphate 1.0% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7%
Aineosat; sekoitetaan ja jauhetaan yhdessä hiekkamyllyssä antamaan hiukkasia, jotka ovat pääasiallisesti kaikki läpi mitaltaan alle 5 mikronia.Ingredients; mixed and ground in one sand mill to give particles that are essentially all through less than 5 microns in size.
Esimerkki 23 Liuos N-Z~(4-metoksi-6-metyylipyrimidin-2-yyli)amino-karbonyyli/-2-klooribentseenisulfoniamidin natrium-suolaa 5 % vettä 95 %Example 23 Solution of the sodium salt of N-Z- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide 5% water 95%
Suola lisätään suoraan veteen sekoittaen antamaan liuos, joka sitten voidaan pakata käyttöä varten.The salt is added directly to the water with stirring to give a solution which can then be packaged for use.
Esimerkki 24Example 24
Rakeet, joilla on pieni väkevyys N-/7(4,6-dimetyylipyrimidin-2-yyli)aminokarbonyyli7- 0,1 % 2,6-d.i klooribentseenisulfoniamid ia attapulgiitti-rakeita (U.S.S. -seulamitta 20-40 mesh) 99,9 % .s 70577Low concentration granules N- [7 (4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -10.1% 2,6-dichlorobenzenesulfonamide and attapulgite granules (USS 20-40 mesh) 99.9% .s 70577
Aktiivinen aineosa liuotetaan liuottimeen ja liuos ruiskutetaan rakeille, joista pöly on poistettu, kaksoiskartiosekoittimessa. Kun liuoksen ruiskutus on loppuunsuoritettu, ainetta kuumennetaan liuottimen haihduttamiseksi. Aineen annetaan jäähtyä ja pakataan sitten.The active ingredient is dissolved in a solvent and the solution is sprayed onto the dedusted granules in a twin cone mixer. When the injection of the solution is completed, the substance is heated to evaporate the solvent. The substance is allowed to cool and then packaged.
Esimerkki 25 Hakee t N-Z’(14,6-dimetoksipyrimidin-2-yyli)-aminokarbo-nyyli.7-2 , 5-diklooribentseenisulfoniamidia 80 %Example 25 Retrieves N-Z '(14,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide 80%
Kostutusainetta 1 % raakaa ligniisisulfonaattisuolaa (sisältää 5-2 0 -o luonnonsokere i ta ) 10 % attapulgiittisavea 9 %Moisturizer 1% crude lignin sulphonate salt (contains 5-20 o-natural sugars) 10% attapulgite clay 9%
Aineosat sekoitetaan ja jauhetaan läpäisemään seulaluvun 100 mesh-seula. Tämä aine lisätään sitten leijupatjarakeistimeen, ilmavirta asetetaan varovasti leijuttamaan ainetta ja hieno vesisuihku suihkutetaan leijutettuun aineeseen. Leijutusta ja suihkutusta jatketaan kunnes saadaan halutun kokoisia rakeita. Suihkutus lopetetaan mutta leijutusta jatketaan, valinnaisesti lämpöä käyttäen kunnes vesipitoisuus on alentunut halutulle tasolle, yleensä alle 1 %:n. Aine poistetaan sitten laitteesta, seulotaan halutulle läpimitta-alueelle, yleensä seulaluvulla 14-100 mesh (1410-149 mikronia), ja pakataan käyttöä varten.The ingredients are mixed and ground to pass through a 100 mesh screen. This material is then added to the fluidized bed granulator, the air stream is carefully set to fluidize the material, and a fine jet of water is sprayed onto the fluidized material. Fluidization and spraying are continued until granules of the desired size are obtained. The spraying is stopped but the fluidization is continued, optionally using heat until the water content has dropped to the desired level, usually below 1%. The material is then removed from the device, screened to the desired diameter range, usually 14-100 mesh (1410-149 microns), and packaged for use.
Esimerkki 2GExample 2G
Erittäin vahva väkevöite N - [i 4,6-d imetyy .1 ipyr i midi n-2-yy 1 i )ami nokarbonyyli7-2-ticfeenisuifoniamidia 99 % silika-aerogeeliä 0,5 % synteettistä amorfista piidioksidia 0,5 %Very strong concentrate N - [i 4,6-dimethyl. 1-pyrimidin-2-yl] aminocarbonyl-2-ticphenenesulfonamide 99% silica airgel 0.5% synthetic amorphous silica 0.5%
Aineosat sekoitetaan ja jauhetaan vasaramyllyssä antamaan aine, josta pääasiallisesti kaikki läpäisee U.S.A. no 50 seulan (0,3 mm:n aukko). Väkevöitettä voidaan muodostella edelleen, jos on tarpeen.The ingredients are mixed and ground in a hammer mill to give a material that is substantially all permeable to U.S.A. no 50 sieve (0.3 mm aperture). Concentrate can be further formed if necessary.
Esimerkki 27 Kostuva jauhe: N-Z”( 4-me toks i- 6-metyy 1 ipyr imi di n-2 -yyli )amino-karbonyyl.i/-2-kIooribentseenisulfoniamid ia 95 % dioktyyiinatriumsulfosukkinaattia 0,1 % synLeettistä hienon piidioksidia 4,9 %Example 27 Wettable Powder: NZ ”(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide 95% dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 4, 9%
IIII
49 7057749 70577
Aineosat, sekoitetaan ja jauhotaan vasaramy 11 yssä antamaan hiukkasia, jotka pääasiallisesti kaikki ovat läpimitaltaan alle 100 mikronia. Aine seulotaan U.S.A. no. 50 seulan läpi ja pakataan. Esimerkki 28 Kostuva jauhe: N-ZT( 4,6-dimet oksi pyrimidin-2-yyli )aminokarbo- nyy li.7-2 , 5-di klooribentseenisulfoniamidia MO % 2,5-diklooribentseenisulfon i amid i a natriumligniinisulfonaattia 20 % montmorilloniittisavea 40 %The ingredients are mixed and ground in a hammer mill to give particles, all of which are substantially less than 100 microns in diameter. The substance is screened in U.S.A. Well. Through a 50 sieve and packed. Example 28 Wettable powder: N-ZT (4,6-dimethoxy-pyrimidin-2-yl) -aminocarbonyl] -2,5-dichloro-benzenesulfonamide MO% 2,5-Dichloro-benzenesulfonamide amide sodium lignin sulfonate 20% montmorillonite clay 40%
Aineosat sekoitetaan perusteellisesti, jauhetaan karkeasti vasaramyllyssä ja sitten ilmamyllyssä antamaan hiukkasia, jotka ovat kooltaan pääasiallisesti kaikki alle 10 mikronia. Aine sekoitetaan uudelleen ja pakataan.The ingredients are mixed thoroughly, coarsely ground in a hammer mill and then in an air mill to give particles substantially all less than 10 microns in size. The substance is remixed and packaged.
Esimerkki 29 01j ysuspensi o N-Z"( M-metoks i-6-metyy 1 ipyrimidin-2-yy 1 L) - 31) o aminokarbonyy117-2-metyyli bentseenisulfoniamidi a pölyä lk j olio 1 ikarbon Ihappoeste re iden j a öljyliukoisten kiviöljysulfonaattien seosta ksyleeniä 59 %Example 29 01.suspension o NZ "(M-methoxy-6-methylpyrimidin-2-yl) -31) aminocarbonyl17-2-methylbenzenesulfonamide dust dust mixture 1 carbonic acid A mixture of acid barriers and oil-soluble petroleum sulfonates in xylene 59%
Aineosat yhdistetään ja jauhetaan yhdessä hiekkamyllyssä antamaan hiukkasia, potka pääasiallisesti kaikki ovat kooltaan alle 5 mikronia. Tuotetta voidaan käyttää suoraan, laimentaa öljyillä tai emulgoida veteen.The ingredients are combined and ground together in a sand mill to give particles, the kicks are basically all less than 5 microns in size. The product can be used directly, diluted with oils or emulsified in water.
Esimerkki 30 Kostuva jauhe N- f( M , 6-d.imetoksi-l, 3,5- tr iät s in-2-yy li ) -aminokarbonyyli/-bentsecnisulfoniamidia 80 % natriumalkyylinaftaleenisulfonaattia 2 % natriumLigniinisulfonaattia 2 % synteettistä amorfista piidioksidia 3 1, kao 1 in i i (. t i α 1 3 7Example 30 Wettable powder N - [(M, 6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium lignin sulfonate 2% synthetic amorphous silica 3 L , Kao 1 in ii (. ti α 1 3 7
Aineosat, sekoitetaan, jauhetaan vasaramyllyssä kunnes kiinteiden aineiden koko on pääasiallisesti, alle 50 mikronia, sekoitetaan uudestaan ja pakataan.The ingredients, mixed, are ground in a hammer mill until the solids size is substantially less than 50 microns, remixed and packaged.
so 70577so 70577
Esimerkki 31 Kostuva jauhe N - £( 4 , 6-d ime tyy li-l,3,5-1riatsin-2-yyli)ain.ino-karbonyyli/bentseenisulfoniamidia 50 % natriumalkyylinaftaleenisulfonaattia 2 % vähäviskoosis ta metyyli selluloosaa 2 % piiinaata 96 %Example 31 Wettable Powder N - [(4,6-dimethyl-1,3,5-triazin-2-yl) amino] carbonyl / benzenesulfonamide 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% silicate 96%
Aineosat sekoitetaan, jauhetaan karkeasti vasaramyllyssä ja sitten ilmamyllyssä antamaan hiukkasia, joista pääasiallisesti kaikki ovat läpimitaltaan alle 10 mikronia. Tuote sekoitetaan uudelleen ennen pakkaamista.The ingredients are mixed, coarsely ground in a hammer mill and then in an air mill to give particles, essentially all of which are less than 10 microns in diameter. The product is remixed before packaging.
Esimerkki 32 RakeetExample 32 Granules
Esimerkin 31 kostuvaa jauhetta 5 % attapulgiittirakeita 95 % (U.S.S. seulaluku 20-90 mesh; 0,84-0,92 mm)Example 31 wettable powder 5% attapulgite granules 95% (U.S.S. screen number 20-90 mesh; 0.84-0.92 mm)
Kostuvan jauheen 1ietettä,joka sisältää n. 25 % kuiva-ainetta, suihkutetaan attapulgiittirakeiden pinnalle kaksoiskartiosekoitti-messa. Rakeet kuivataan ja pakataan.A wettable powder slurry containing about 25% dry matter is sprayed onto the surface of the attapulgite granules in a double cone mixer. The granules are dried and packaged.
Esimerkki 33Example 33
Suulakepuristettu pilleri: N-/"(4-metoksi-6-metyyli-l,3,5-triatsin-2-yyli)-aminokarbonyyli7-2-klooribentseenisulfoniamidia 25 % vedetöntä natriumsulfaattia 10 % raakaa kalsiumligniinisulfonaattia 5 % natriumalkyylinaftaleenisulfonaattia 1 % kalsium/magnesiumbentoniittiä 59 %Extruded pill: N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide 25% anhydrous sodium sulfate 10% crude calcium lignin sulfonate 5% sodium alkylnaphthalene sulfonate sulfonate sulfonate sulfonate sulfonate 59%
Aineosat sekoitetaan, jauhetaan vasaramyllyssä ja kostutetaan sitten n. 12 %:lla vettä. Seos suulakepuristetaan läpimitaltaan n.The ingredients are mixed, ground in a hammer mill and then moistened with about 12% water. The mixture is extruded with a diameter of approx.
3 mm:n sylintereiksi, jotka leikataan antamaan n. 3 mm:n pituisia pillereitä. Näitä voidaan käyttää suoraan kuivaamisen jälkeen tai' kuivatut p>.i lierit voidaan murskata läpäisemään U.S.S. seula (0,84 mm:n aukot). Rakeet, jotka pysyvät U.S.S. no. 40seulalla (0,42 mm:n aukot) voidaan pakata käyttöä varten ja hienot palautetaan.Into 3 mm cylinders cut to give pills about 3 mm long. These can be used directly after drying or the dried pellets can be crushed to pass the U.S.S. sieve (0.84 mm apertures). Granules that remain U.S.S. Well. A 40-mesh screen (0.42 mm openings) can be packed for use and the fins returned.
51 7057751 70577
Esimerkki 35 Öljysuspensio N - Z~( 4 , 6 — cl ime toks i-1,3 ,5- tr id t s in-2-yy 1 i ) ami no- 2 3 % karbonyyj i_7 — 2 — kloori -5-metoksibentseenisulfon-amicl ia polyokcieteenisorbitoliheksaoleaattia 5 % erittäin aiiiau11is La h i i 1 i ve Lyöt jyä 70 %Example 35 Oil suspension N-Z- (4,6-climethoxy-1,3,5-tridazin-2-yl) amino-3 3% carbonyl-7-chloro-5-methoxybenzenesulfon -amycl and polyoctylene sorbitol hexaoleate 5% very aiiiau11is La hii 1 i ve Beat 70%
Aineosat jauhetaan yhdessä hiekkamyllyssä kunnes kiinteiden hiukkasten läpimitta on pienentynyt alle n, 5 mikronin. Saatua suspensiota voidaan käyttää suoraan, mutta edullisesti senjälkeen, kun se on laimennettu öljyllä tai emulgoitu veteen.The ingredients are ground in one sand mill until the diameter of the solid particles has decreased to less than n, 5 microns. The resulting suspension can be used directly, but preferably after being diluted with oil or emulsified in water.
Esimerkki 35 Kostuva jauhe N-ZT( 4,6-d i me toksi-1,3,5-triatsin-2-yyli ) amino- 20 % karbonyyj i/-2-klooribentseenisulhoniamidi a natr.iuma J kyy 1 i naf taleenisul fonaattia 4 % natriuml igni inisulf onaattia 4 '0 vähäviskoosista metyyliselluloosaa 3 % attapulgiittia 69 %Example 35 Wettable Powder N-ZT (4,6-dimethoxy-1,3,5-triazin-2-yl) amino-20% carbonyl] -2-chlorobenzenesulfonamide and sodium J naphthalene sulfonate 4% sodium sulphonate 4 '0 low viscosity methylcellulose 3% attapulgite 69%
Aineosat sekoitetaan perusteellisesti. Jauhamisen jälkeen vasaramyllyssä hiukkasten saamiseksi, joista pääasiallisesti kaikki ovat läpimitaltaan alle 100 mikronia, aine sekoitetaan uudelleen ja seulotaan U.S.S. no. 50 seulan (0,30 mm:n aukko) läpi ja pakataan. Esimerkki 3b 01j ysuspens io N-£(4,G-d imetoksi-1,3,5-triatsin-2-yyli)amino-karbonyyli./-bentseenisulfoniamidia 3 5 % polyalkoholikarbonihappoestereiden ja 6 % öljyliukoisten kivioljysulfonaattien seosta ksyleeniä 5 9 %The ingredients are mixed thoroughly. After grinding in a hammer mill to obtain particles, substantially all of which are less than 100 microns in diameter, the material is remixed and screened by U.S.S. Well. Through a 50 sieve (0.30 mm orifice) and packed. Example 3b 01j Suspension of N- (4,1G-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -benzenesulfonamide
Aineosat yhdistetään ja jauhetaan yhdessä hiekkamyllyssä antamaan hiukkasia, jotka pääasiallisesti kaikki ovat läpimitaltaan alle 3 mikronia. Tuotetta voidaan käyttää suoraan, laimentaa öljyillä tai emuigoida veteen.The ingredients are combined and ground in one sand mill to give particles, essentially all less than 3 microns in diameter. The product can be used directly, diluted with oils or emulsified in water.
52 7057752 70577
Esimerkki 37Example 37
Erittäin väkevä väkevöite N-f(4,6-dimetoksi-l,3, S-triats in-2-yyli)- 99 % aminokarbonyy1i7 bentseenisulfoniamidia silika-aerogeeliä 0,5 % synteettistä amorfista piidioksidia 0,5 %Highly concentrated N-f (4,6-dimethoxy-1,3,5-triazin-2-yl) -99% aminocarbonyl-177 benzenesulfonamide silica air gel 0.5% synthetic amorphous silica 0.5%
Aineosat sekoitetaan ja jauhetaan vasaramyllyssä antamaan aine, josta pääasiallisesti kaikki läpäisee U.S.S. no. 50 seulan (aukko 0,3 mm). Väkevöitettä voidaan muodostella edelleen, jos on tarpeen.The ingredients are mixed and ground in a hammer mill to give a material that is substantially all permeable to U.S.S. Well. 50 sieve (aperture 0.3 mm). Concentrate can be further formed if necessary.
Esimerkki 38Example 38
Rakeet, joilla on pieni pitoisuus N-/”( 4-metoksi-6-metyyli-1,3,5-triatsin-2-yyli ) - 1 % aminokarbonyyli/-2-kloori-5-metoksibentseenisul- foniamidia N ,N-dimetyyliformamidi a 9 % attapulgiittirakeita 90 % (U.S.S. seulakoko 20-40 mesh).Granules with a low content of N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -1% aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide N, N- dimethylformamide a 9% attapulgite granules 90% (USS sieve size 20-40 mesh).
Aktiivinen aineosa liuotetaan liuottimeen ja liuosta suihkutetaan rakeille, joista pöly on poistettu, pyörivässä sekoittimessa. Senjälkeen kun liuoksen suihkutus on loppuunsuoritettu, annetaan sekoittimen pyöriä lyhyen ajan ja rakeet pakataan.The active ingredient is dissolved in a solvent and the solution is sprayed onto the dedusted granules in a rotary mixer. After the spraying of the solution is completed, the stirrer is allowed to run for a short time and the granules are packed.
Esimerkki 39 Vesipitoinen suspensio N-4,6-dimetyyli-1,3,5-triatsin-2-yyli)- 40 % aminokarbonyyli/-bentseenisulfoniamidia polyakryyl.ihappopaksunninta 0,3 % dodekyylifenolipolyeteeniglykolieetteriä 0,5 % dinatriumfosfaattia 1 % mononatriumfosfaattia 0,5 % polyvinyylialkoholia 1,0 % vettä 56,7 %Example 39 Aqueous suspension of N-4,6-dimethyl-1,3,5-triazin-2-yl) - 40% aminocarbonyl / benzenesulfonamide polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium phosphate % polyvinyl alcohol 1.0% water 56.7%
Aineosat sekoitetaan ja jauhetaan yhdessä hiekkamyllyssä antamaan hiukkasia, jotka pääasiallisesti kaikki ovat kooltaan alle 5 mikronia.The ingredients are mixed and ground together in a sand mill to give particles, essentially all less than 5 microns in size.
it 53 70577it 53 70577
Esimerkki MU Liuos N-Z(4-metoksi-6-metyyli-l,3,5-triatsin-2-yyli)-aminokarbonyy li_7-2-klooribent seen isul f on iamid in natriumsuolaa 5 % vettä 95 oExample MU Solution N-Z (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl-7-2-chlorobenzenesulfonyl isamide sodium salt 5% water 95 ° C
Suola lisätään suoraan veteen sekoittaen antamaan liuos, joka sitten voidaan pakata käyttöä varten.The salt is added directly to the water with stirring to give a solution which can then be packaged for use.
Esimerkki 91 Rakeet N - Z"( 4,6-dimetoksi-l,3 ,5-triatsin-2-yyli)amino karbonyy 1 i]- 2 , 5-dimetoks ibentseenisul f oniaini dia 80 % kostutusainetta 1 % raakaa ligniinisulfonaattisuolaa (joka sisältää 5-20 % luonnon sokereita) attapulgiittisavea 9 %Example 91 Granules N - Z "(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2,5-dimethoxybenzenesulfonine dia 80% wetting agent 1% crude lignin sulfonate salt (which contains 5-20% natural sugars) attapulgite clay 9%
Aineosat sekoitetaan ja jauhetaan läpäisemään seulaluvun 100 mesh seula. Tämä aine lisätään sitten leijupatjarakeistimeen, ilmavirta asetetaan varovasti leijuttamaan ainetta ja hieno vesisuihku suihkutetaan leijutettuun aineeseen. Leijutusta ja suihkutusta jatketaan kunnes saadaan rakeita halutulta läpimitta-alueelta. Suihkuttaminen lopetetaan, mutta leijutusta jatketaan, valinnaisesti lämpöä käyttäen, kunnes vesipitoisuus on alentunut halutulle tasolle, yleensä alle 1 %:n. Aine poistetaan sitten laitteesta, seulotaan halutulle läpimitta-alueelle, yleensä seulalukuun 14-100 mesh (1410-149 mikronia), ja pakataan käyttöä varten.The ingredients are mixed and ground to pass through a 100 mesh screen. This material is then added to the fluidized bed granulator, the air stream is carefully set to fluidize the material, and a fine jet of water is sprayed onto the fluidized material. Fluidization and spraying are continued until granules of the desired diameter range are obtained. Spraying is stopped, but fluidization is continued, optionally using heat, until the water content has dropped to the desired level, usually less than 1%. The material is then removed from the device, screened to the desired diameter range, usually 14-100 mesh (1410-149 microns), and packaged for use.
E s i me rkki 4 2E s i me rkki 4 2
Rakeet, joilla on pieni pitoisuus N-Li4-metoksi-6-metyyli-1,3,5-triatsin-2-yyli)- 0,1 % aminokarbonyy1i7- 2-klooribentseenisuifoniamidia attapulgiittirakeita 99,9 % (U.S.S. seulaluku 20-40 mesh)Granules with a low content of N-Li4-methoxy-6-methyl-1,3,5-triazin-2-yl) - 0.1% aminocarbonyl-7-2-chlorobenzenesulfonamide 99.9% attapulgite granules (USS screen number 20-40 mesh )
Aktiivinen aineosa liuotetaan liuottimeen ja liuos suihkutetaan rakeille, joista pöly on poistettu, kaksoiskartiosekoittimessa. Senjälkeen kun liuoksen suihkutus on loppuunsuoritettu, ainetta kuumennetaan liuottimen poistamiseksi. Aineen annetaan jäähtyä ja pakataan sitten.The active ingredient is dissolved in a solvent and the solution is sprayed onto the dedusted granules in a twin cone mixer. After spraying the solution is complete, the material is heated to remove the solvent. The substance is allowed to cool and then packaged.
s. 70577pp. 70577
Esimerkki M3 Kostuva jauhe N-/’(4-metoksi-6-metyyli-l,3,5-triatsin-2-yyli)- 95 % aminokarbonyyli/-2-kloori-5-metoksibentseeni-sulfoniamidia dioktyylinatriumsulfosukkinaattia 0,1 % synteettistä hienoa piidioksidia 4,9 %Example M3 Wettable powder N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -95% aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 4.9%
Aineosat sekoitetaan ja jauhetaan vasaramyllyssä antamaan hiukkasia, jotka kooltaan pääasiallisesti kaikki ovat alle 100 mikronia. Aine seulotaan U.S.S. no. 50 seulan läpi ja pakataan.The ingredients are mixed and ground in a hammer mill to give particles that are substantially all less than 100 microns in size. The substance is screened by U.S.S. Well. Through a 50 sieve and packed.
Esimerkki 44 Kostuva jauhe N-Z"(4-metoksi-6-metyyli-l,3,5-triatsin-2-yyli)- 40 % aminokarbonyyli7-2-klooribentseenisulfoniamidia natriumligniinisulfonaattia 20 % montmorilloniittisavea 40 %Example 44 Wettable Powder N-Z "(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -40% aminocarbonyl-2-chlorobenzenesulfonamide sodium lignin sulfonate 20% montmorillonite clay 40%
Aineosat sekoitetaan perusteellisesti, jauhetaan karkeasti vasaramyllyssä ja sitten ilmamyllyssä antamaan hiukkasia, jotka pääasiallisesti kaikki ovat kooltaan alle 10 mikronin. Aine sekoitetaan uudelleen ja pakataan sitten.The ingredients are mixed thoroughly, coarsely ground in a hammer mill and then in an air mill to give particles, substantially all less than 10 microns in size. The substance is mixed again and then packaged.
Kaavan I yhdisteitä voidaan muodostaa käyttäen esimerkkien 15-44 menetelmiä.The compounds of formula I can be formed using the methods of Examples 15-44.
HyväksikäyttöExploitation
Kaavan I yhdisteet ovat käyttökelpoisia rikkaruohomyrkkyinä. Niitä voidaan käyttää joko ennen tai jälkeen ilmaantumisen ei-toi-votun kasvullisuuden torjumiseksi alueilla, jotka eivät ole viljelyksessä, ja rikkaruohojen torjuntaan tietyissä viljalajeissa, esim. vehnässä. Jotkut näistä yhdisteistä ovat käyttökelpoisia pähkinä-saran torjuntaan ennen ja/tai jälkeen ilmaantumisen viljelykasveissa, kuten puuvillassa, maississa ja riisissä. Valitsemalla sopivasti käyttömäärä ja -aika, tämän keksinnön yhdisteitä voidaan käyttää kasvien kasvun muunteluun edullisesti.The compounds of formula I are useful as herbicides. They can be used either before or after emergence to control unwanted vegetation in non-cultivated areas and to control weeds in certain cereals, e.g. wheat. Some of these compounds are useful for controlling nut Sara before and / or after emergence in crops such as cotton, corn and rice. By appropriately selecting the amount and time of application, the compounds of this invention can be advantageously used to modify plant growth.
Kaavan I yhdisteen jossakin annetussa tilanteessa käytettävä tarkka määrä vaihtelee riippuen halutusta nimenomaisesta lopputuloksesta, kyseessä olevasta käyttötavasta, torjuttavista rikkaruohoista, maaperätyypistä, valmistemuodosta ja levitystavasta, sääolosuhteista ja niiden kaltaisista tekijöistä. Koska mukana on vaikuttamassa näin 70577 5 3 monia muuttujia, ei oJe mahdollisia määrätä Jovi l y n määräät, joka olisi sopiva kaikkiin tilanteisiin. Yleisesti ottaen tämän keksinnön yhdisteitä käytetään määrissä väliltä 0,005-20 kg/ha edullisen välin ollessa 0,01-10 kg/ha. Alueen alemmat määrät valitaan yleensä ke-veimmille maaperille, rikkaruohojen selektiivistä torjuntaa varten viljakasveissa tai tilanteissa, joissa maksimaalinen jatkuvuus ei ole tarpeen. Joitakin kaavan I yhdisteitä voidaan käyttää hyvin pienissä määrissä kasvin kasvun muunteluun, mutta myös suuremmat määrät voivat olla käyttökelpoisia riippuen sellaisista tekijöistä kuin käsiteltävästä kasvista, käsittelyn ajoituksesta jne.The exact amount of a compound of formula I to be used in a given situation will vary depending on the particular end result desired, the particular application, the weeds to be controlled, the type of soil, the formulation and method of application, the weather conditions and the like. Since 70577 5 3 many variables are involved, it is not possible to determine the quantities of Jovi l y n that would be suitable for all situations. In general, the compounds of this invention are applied in amounts ranging from 0.005 to 20 kg / ha, with a preferred range of 0.01 to 10 kg / ha. Lower amounts in the area are usually selected for the lightest soils, for selective weed control in cereals or in situations where maximum continuity is not necessary. Some compounds of formula I may be used in very small amounts to modify plant growth, but higher amounts may also be useful depending on factors such as the plant being treated, the timing of treatment, etc.
Kaavan I yhdisteitä voidaan käyttää yhdessä muiden rikkaruo-homyrkkyjen kanssa ja erityisen käyttökelpoisia ne ovat yhdistelmänä 3-(3,4-dik.loorifenyy1i)-1,1-dimetyy1!urea , trials 1inien, kuten 2-kloori - 4 - ( e tyy Liemi no) - ϋ - ( i s o pr o pyy 1 i am i no) - s - t r ia t s i i n in kari s s a , urasiilien, kuten 5-bromi-3-sek.-butyyli-6-metyy1iurasiiIin, N-(fosfonimetyy1i)glysiinin, 3-sykloheksyy1i-1-mo tyy1i-h-di me tyyli-amino-s-triatsiini-2 , 4(1H , 3H)-dionin, N,N-dimetyyli-2,2-difenyyli-asetamidin, 2,4-dikloorifenoksietikkahapon (sekä lähisukuisten yhdisteiden) kanssa, 4-kloori-2-butynyy1i- 3-kloorifenyy1i karbamaa- (D) tin (Carbyne^'n) , di-isopropyyl i t i olikarbam L in.ihapon esterin kanssa, iT*\ 2 , 3-diklooriallyylialkoholin (Avadex^1 in), di-isopropyylitiölikar- ... (ph bamunihapon, S-(2,3,3-triklooriallyyliesterin (Avadex^ BW:n), etyyli-n-bentsoyy 1 ,i - N- ( 3,4-dik loori f enyy 1 i ) - 2 -aminopropionaat in (r) ( Suffix' m), 1,2-dimetyy1i- 3,5-difenyy1i-pyratsoilumme tyyli-su i-f aatin (Avenge®' in ), metyyli-/-£4-(2,4-d ikioorif enoks i)-fenoksi?-propanoaatin (Hoe1on®' in), 4-amino-6-1ert.-butyy1i-3-(metyy1it i o)-1,2,4-triats in-b(4H)-onin (Lexone®' in) , 3-(3,4-dikloori fenyy1i)-] -metoks i-1-metyyliurean ( Loroji®' in) kanssa, 3-isopropyyli-lH-2,1,3-bentsotiodiats in- ( 4 ) - 3H-oni-2 , 2-dioks idin , o( ·,ο(,σ{ -trifluori-2,6-di-nitro-N,N-dipropyyli-p-toluidi ini n, 1,1'-di me tyy1i--,4'-bipyrid i n ium-ionin , mononatrium-metaaniarsonaatin , 2-kloori-2 -d ; etyyli -(me toks imetyy 1 i ) ase tan i lidin ja 1 ,1 - dime tyy 1 i- 3- (0(, ^ , ex’ - tri fluori-m-tolyyli )-urean ( Cotoraii®'in ) kanssa.The compounds of formula I may be used in combination with other herbicides and are particularly useful in combination with 3- (3,4-dichlorophenyl) -1,1-dimethylurea, Trialsins such as 2-chloro-4- Broth no) - ϋ - (isopropylamine) s-triazine in Kari, uracils such as 5-bromo-3-sec-butyl-6-methyluracil, N- (phosphonomethyl) glycine, 3-cyclohexyl-1-methyl-h-dimethylamino-s-triazine-2,4 (1H, 3H) -dione, N, N-dimethyl-2,2-diphenylacetamide, 2, With 4-dichlorophenoxyacetic acid (and related compounds), 4-chloro-2-butynyl-3-chlorophenylcarbamate (D) thin (Carbyne), diisopropylitolicarbamic acid ester, iT * \ 2 , 3-dichloroallyl alcohol (Avadex ^ 1 in), diisopropylthiocarboxylate (pham bamic acid, S- (2,3,3-trichloroallyl ester (Avadex ^ BW)), ethyl-n-benzoyl 1, i-N - (3,4-dichlorophenyl) -2-aminopropionate (r) (Suffix 'm), 1,2-dimethyl-3,5-diphenylpyrazole mmethyl sulfate (Avenge®), methyl N- [4- (2,4-dichlorophenoxy) phenoxy] propanoate (Hoeonon®), 4-amino-6-1ert. -butyl-3- (methylthio) -1,2,4-triazin-b (4H) -one (Lexone®), 3- (3,4-dichlorophenyl)] - methoxy-1- with methyl urea (Loroji® '), 3-isopropyl-1H-2,1,3-benzothiodiazine- (4) -3H-one-2,2-dioxide, o (·, ο (, σ {-trifluoro -2,6-di-nitro-N, N-dipropyl-p-toluidine, 1,1'-dimethyl, 4'-bipyridinium ion, monosodium methanesononate, 2-chloro-2 -d; with ethyl - (methoxymethyl) acetane and 1,1-dimethyl-3- (O (O, ex'-trifluoro-m-tolyl) urea (Cotorai®)) .
Näiden yhdisteiden aktiivisuus havaittiin kasvihuonetesteissä. Testit on selostettu ja niistä saadut tulokset on esitetty seuraa-vas sa.The activity of these compounds was observed in greenhouse tests. The tests are described and the results obtained are shown below.
56 n O 5 7 756 n O 5 7 7
Testimenetelmätest method
Ryömivän rikkaruohon (DigiLaria-laji), piharuohon Echinochloa crusgalli), hukkakauran (Avena Tatua), Cassia tora'n, Ipomea-lajin, takiaisen (Xanthium-lajin), hirssin, maissin, soija-pavun, riisin, vehnän siemeniä ja pähkinäsaran juurimukuloita istutettiin kasvuvällaineeseen ja käsiteltiin ennen ilmaantumista kemikaaleilla liuotettuina kasveille myrkyttömään luottimeen. Samaan aikaan ruiskutettiin puuvillaa, jossa oli 5 lehteä (sirkkalehdet mukaanluettuina), pensaspapuja, joissa kolmas lehti kolmilehtisestä lehdistöstä oli avautumassa, kaksi lehtistä ryömivää rikkaruohoa, piharuohoa, jossa oli kaksi lehteä, yksilehtistä hukkakauraa, kas-siaa, jossa oli kolme lehteä (sirkkalehdet mukaanluettuna), nelilehtistä Ipomea-lajia (sirkkalehdet mukaanluettuina), nelilehtistä takiaista (sirkkalehdet mukaanluettuina), kolmilehtistä hirssiä, maissia, jossa oli kolme lehteä, soijapapua, jossa oli kaksi sirkka-lehteä, riisiä, jossa oli kaksi lehteä, yksilehtistä vehnää ja kolme - viisilehtistä pähkinäsaraa. Käsiteltyjä kasveja ja vertailu-kasveja pidettiin kasvihuoneessa 16 päivää, sitten kaikkia lajeja verrattiin vertailuihin ja reagointi käsittelyyn arvosteltiin silmämääräisesti. Arvostelut kasveille, jotka on testattu tällä menetelmällä, on esitetty taulukossa IX.Seeds of creeping weeds (DigiLaria species), yard grass (Echinochloa crusgalli), oats (Avena Tatua), Cassia tora, Ipomea, burdock (Xanthium species), millet, maize, soybeans, rice and wheat seeds were implanted in growth medium and treated with chemicals dissolved in plants in a non-toxic solvent before emergence. At the same time, cotton with 5 leaves (including cotyledons), shrub beans with a third leaf from a three-leaf press opening, two leaf-crawling weeds, a yard with two leaves, a single-leaf waste oat, a box with three leaves (sprayed with cotyledons) were sprayed ), four-leaf Ipomea (including cotyledons), four-leaf burdock (including cotyledons), three-leaf millet, maize with three leaves, soybeans with two Sirkka leaves, rice with two leaves, single-leaf wheat and three to five-leaf nutsedge. Treated plants and control plants were kept in a greenhouse for 16 days, then all species were compared to controls and the response to treatment was evaluated visually. Reviews for plants tested by this method are shown in Table IX.
0 = ei vaikutusta & tai 10 = suurin vaikutus B = palanut C = kalvetusta tai kudoskuolemaa D = lehtien putoamista E - esiinpuhkeaminen estyy G = kasvu hidastuu H = muovaavia vaikutuksia 1 = lisääntynyttä vihertymistä L = itäminen P = päätesilmut kuolevat S = albinismi U = epätavallinen pigmen to.i tuminen 6Y = nuput tai kukut putoavat VZ = takautuminen X = lehtihankoja kiihottava vaikutus.0 = no effect & or 10 = maximum effect B = burnt C = desiccation or tissue death D = leaf fall E - emergence is prevented G = growth is slowed down H = shaping effects 1 = increased greening L = germination P = end buds die S = albinism U = unusual pigment to.i tion 6Y = buds or cocks fall VZ = retraction X = effect on leaf rubbing.
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Keksinnön yhdisteiden hyödyllisyys rikkaruohojen selektiivisessä torjunnassa vehnässä havaittiin ensiksi joukossa kasv ihuonetesteja Seuraavassa kuvatut neljä testiä (A, B, C ja D) kuvaavat tätä hyötyä.The utility of the compounds of the invention in the selective control of weeds in wheat was first observed in a number of growth dermal tests. The four tests described below (A, B, C and D) illustrate this benefit.
Testi ATests A
Kaksi 25 cm"n läpimittaista pallomaista muovikuppia täytettiin lannoitetulla ja kalkitulla Fallsington-1ietesavimaallu. Yhteen kuppiin istutettiin maiss i. , hirssiä ja useita ruohomaisia rikkaruohoja. Toiseen kuppiin istutettiin soijapapuja, purppuranpunaista pähkinä-saraa (Cyperus rotundus) ja useita leveä leht I s .iä rikkaruohoja. Istutettiin seuraavia ruohomaisia ja leveälehtisiä lajeja: ryömivää rikkaruohoa (Digitaria sanguinalis), piharuohoa (Echinochloa crusgalli), hukkakauraa (Avena fatua), johnson-ruohoa (Sorghum halepence), jätti-läispuntarpaätä (Setaria faberii ) , Kentucky1!! siniruohoa (Poa pratensi valeruohoa (Bromus secalinus), sinappia (Brassicu arvensis), takiaista (Xanthium pennsylvanicum), sian ruohoa (Amaranthus retroflexus), kiharaa indigoa (Aeschynomene Virginiaa), Ipomea-lajia (Ipomea hede-racea), kass.iaa (Cassia tora), teeruohoa (Sida spinosa), sametti-lehteä (Abutilon theophrasti) sekä j .imson-ruohoa (Datura stramonium). Lisäksi kaksi läpimitaltaan 12,5 cm:n paperikupp ia täytettiin seostetulla kasvukerrokse1la; toiseen istutettiin riisiä ja vehnää ja toiseen sokerijuurikasta. Näitä neljää astiaa käsiteltiin ennen ilmaantumista, ts. yhdisteitä ruiskutettiin kasvukerrosten pinnalle ennen siemenen itämistä.Two 25 cm diameter spherical plastic cups were filled with fertilized and limed Fallsington-1 clay soil. One cup was planted with corn, millet, and several herbaceous weeds. The following herbaceous and broadleaf species were planted: creeping weed (Digitaria sanguinalis), yarrow (Echinochloa crusgalli), oats (Avena fatua), johnson grass (Sorghum halepence), giant (Sorghum halepence); pratenssi false grass (Bromus secalinus), mustard (Brassicu arvensis), burdock (Xanthium pennsylvanicum), porcine grass (Amaranthus retroflexus), curly indigo (Aeschynomene Virginia), Ipomea species (Ipomea hede-racea), kass. , tea grass (Sida spinosa), velvet leaf (Abutilon theophrasti) and j .imson grass (Datura stramonium), as well as two 12.5 cm diameter the paper cup was filled with the doped growth layer; one was planted with rice and wheat and the other with sugar beet. These four vessels were treated before emergence, i.e., the compounds were sprayed onto the surface of the growth layers before seed germination.
28 päivää käsittelyn jälkeen kasvit arvosteltiin. Saadut tulokse on koottu taulukkoon X. On huomattava, että vehnä sietää testattuja yhdisteitä paremmin kuin useimmat rikkaruoho]ajit.28 days after treatment, the plants were evaluated. The results obtained are summarized in Table X. It should be noted that wheat tolerates the tested compounds better than most weeds.
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2 5 cm: n läpimittaisiin muovi ruukkuiin in, jotka oli täytetty Fallsington-lietesavimaalla, istutettiin soijapapua, puuvillaa, lusernia, maissia, riisiä, vehnää, hirssiä, samettilehteä (Abutilon Theophrasti), sesbaniaa (Sesbania exaltata), kassiaa (Cassia tora), Ipomoea-lajia, jimson-ruohoa (Datura stramonium), takiaista (Xanthium pennsylvanicum), ryömivää rikkaruohoa (Digitaria-lajia), pähkinäsaraa (Cyperus rotundus), piharuohoa (Echinochloa crusgalli), jättikäispun-tarpäätä (Setaria faberii) ja hukkakauraan (Avena fatua). N. 2,5 viikkoa istuttamisen jälkeen nuoria taimia ja kasvukerrosta niiden ympärillä ruiskutettiin kauttaaltaan testikemikaaleilla liuotettuina kasveille myrkyttömään liuottimeen. 14 päivää käsittelyn jälkeen kaikkia lajeja verrattiin käsittelemättömiin vertailuihin ja niiden reaktio käsittelylle arvosteltiin silmämääräisesti. Saadut tulokset on esitetty taulukossa XI.2 Soybeans, cotton, alfalfa, corn, rice, wheat, millet, velvet leaf (Abutilon Theophrasti), sesbania (Sesbania exaltata), cassia (Cass) were planted in 2 5 cm diameter plastic pots filled with Fallsington sludge. Ipomoea species, jimson grass (Datura stramonium), burdock (Xanthium pennsylvanicum), crawling weed (Digitaria species), nutcracker (Cyperus rotundus), yarrow (Echinochloa crusgalli) ). About 2.5 weeks after planting, the young seedlings and the growth layer around them were sprayed throughout with test chemicals dissolved in a non-toxic solvent for the plants. 14 days after treatment, all species were compared to untreated controls and their response to treatment was evaluated visually. The results obtained are shown in Table XI.
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Yhdisteitä levitetiin kasveille myrkyttömässä liuottimessa ilmaantumisen jälkeen kauttaaltaan ruiskuttaen seuraavien kasvien istutukset: vehnä (korkeus 11 cm» 2-lehtisessä vaiheessa), hukka-kaura (Avena fatua), (korkeus 9 cm, 1-lehtisessä vaiheessa), Bromus testorum (korkeus 5 cm, 1-lehtisessä vaiheessa), B, secalinus (korkeus 5 cm, l-lehtisessa vaiheessa), mustaruoho (Alopecurus myosuroides) (korkeus 3 cm, 1-lehtisessä vaiheessa) sekä yksivuotinen pyörtänoluste (Lolium multiforum) (korkeus 8 cm, 1-lehtisessä vaiheessa), sekä myös samojen lajien istutukset ennen ilaamtnumista. Kaikki istutukset olivat läpimitaltaan 25 cm:n kasvukerroskupeissa. Testikohteita pidettiin kasvihuoneessa ja arvotelu kasvien reagoinnista suoritettiin 5 viikkoa levityksen jälkeen. Tulokset näistä testeistä on esitetty taulukossa XII.The compounds were applied to the plants after emergence in a non-toxic solvent by spraying throughout the plantings of the following plants: wheat (height 11 cm »2-leaf stage), wasted oats (Avena fatua), (height 9 cm, 1-leaf stage), Bromus testorum (height 5 cm , In 1-leaf stage), B, secalinus (height 5 cm, in 1-leaf stage), black grass (Alopecurus myosuroides) (height 3 cm, in 1-leaf stage) and annual lolium multiforum (height 8 cm, 1-leaf stage) leaf stage), as well as plantings of the same species before germination. All plantings were in 25 cm diameter growth layer cups. Test subjects were kept in a greenhouse and evaluation of plant response was performed 5 weeks after application. The results of these tests are shown in Table XII.
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Testi DTests D
Yhdisteitä levitettiin kasveille myrkyttömässä liuottimessf suihkeena kauttaaltaan seuraaville esiinpuhjenneille (jälkeen ilme tumisen) istutetuille kasveille: vehnä, 22 cm:n korkuista, hukkako (Avena fatua) , korkeus IM cm, Bromus testorum, korkeus 3 cm, Bromi secalinus, korkeus 5 cm, ohra, korkeus 22 cm, Kochia scoparia, korkeus b cm, villamamomiJle (Matricaria inodora), korkeus 3 cm, \ lisinappi (Brassica arvensis) , korkeus 7 cm, Lupatorium capillifoi sekä tatar (Polygonum convolvulus), korkeus 6 cm, ja samojen lajie istutuksille ennen ilmaantumisen, kaikki astutettuina kasvukerroks sisältäviin ruukkuihin. Testikohteita pidettiin kasvihuoneessa ja arvostelut taimien reagoinnista tehtiin M viikkoa levityksen jälke jolloin saatiin taulukossa XIII esitetyt tulokset.The compounds were applied to the plants in a non-toxic solvent spray throughout the following emergent (post-emergence) planted plants: wheat, 22 cm high, Avena fatua, height IM cm, Bromus testorum, height 3 cm, Bromi secalinus, height 5 cm, , height 22 cm, Kochia scoparia, height b cm, woolly momiJle (Matricaria inodora), height 3 cm, \ additional button (Brassica arvensis), height 7 cm, Lupatorium capillifoi and buckwheat (Polygonum convolvulus), height 6 cm, and plantings of the same species before emergence, all mated in pots containing the growth layer. Test subjects were kept in a greenhouse and evaluations of seedling response were made M weeks after application to give the results shown in Table XIII.
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Seuraavat lukuarvot osoittavat tämän keksinnön yhdisteiden arvon pähkinäsaran torjunnassa.The following numerical values indicate the value of the compounds of this invention in controlling the nutcracker.
Pähkinäsaran (Cyperus rotundus) juurimukuloita (5 kpl ruukkua kohti) istutettiin n. 2,5 cm:n syvyyteen 10 cm:n ruukkuihin, jotka sisälsivät Fallsington-lietesavimaata. Jokaista arvosteltavaa yhdistettä levitettiin kasvukerroksen pintakäsittelysuihkeena ennen ilmaantumista, suunnattuna juurimukulasuihkeena, niitä yhdistettiin kauttaaltaan kasvukerroksen päällimmäiseen 2,5 cm:n kerrokseen ja ruiskutettiin ilmaantumisen jälkeen n. 8-10 cm:n korkeuisten taimien lehdistöille. Yhdisteet liuotettiin sopivaan liuottimeen ja levitettiin ruiskutustilavuudessa 560 1/ha. Kemiallisen käsittelyn vaikutukset taimen kasvuun arvosteltiin silmämääräisesti 4 viikkoa käsittelyn jälkeen, kuten taulukossa XIV on esitetty.Root tubers of nutcracker (Cyperus rotundus) (5 per pot) were planted to a depth of about 2.5 cm in 10 cm pots containing Fallsington sludge clay. Each compound to be evaluated was applied as a growth layer surface treatment spray before emergence, directed as a tuber spray, was combined throughout the top 2.5 cm layer of the growth layer, and after emergence was sprayed on presses of seedlings about 8-10 cm high. The compounds were dissolved in a suitable solvent and applied at a spray volume of 560 l / ha. The effects of chemical treatment on seedling growth were evaluated visually 4 weeks after treatment, as shown in Table XIV.
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Eräässä toisessa testissä havaittiin, että tämän keksinnön yhdisteet ovat hyödyllisiä pähkinäsaran selektiiviseen torjuntaan, vilj akasve issa.In another test, the compounds of this invention were found to be useful in the selective control of nutcrack in crops.
Useita 25 cm: n läpimittaisia muovikuppeja, jotka oli vuorattu polyeteenivuorauksi1la, täytettiin Fallsington-lietesavimaalla ja kuhunkin kuppiin .istutettiin 2,5 cm:n syvyyteen seuraavien kasvien siemeniä: maissi (Zea mays), soijapapu (Glycine max), riisi (Oryza sativa), puuvilla (Gossypium hirsutum) ja pähki nasai’an juurimukuloita (Cyperus rotundus). Jokainen arvosteltava yhdiste liuotettiin sopivaan liuottimeen ja levitettiin ennen ja jälkeen ilmaantumisen ruiskutus-tilavuudessa 560 1/ha. Esiinpuhkeamisen jälkeen käsitellyt kasvit olivat korkeudeltaan 6-14 crn:n välillä käsittelyn ajankohtana. 4 viikkoa käsittelyn jälkeen kemiallisen käsittelyn vaikutukset kasvien kasvuun arvosteltiin silmämääräisesti kuten taulukossa XV on esitetty.Several 25 cm diameter plastic cups lined with polyethylene liner were filled with Fallsington sludge clay and seeded with 2.5 cm deep seeds of the following plants: corn (Zea mays), soybean (Glycine max), rice (Oryza sat) , cotton (Gossypium hirsutum) and walnut nasai root tubers (Cyperus rotundus). Each compound to be evaluated was dissolved in a suitable solvent and applied before and after emergence in an injection volume of 560 l / ha. After emergence, the treated plants ranged in height from 6 to 14 cm at the time of treatment. 4 weeks after treatment, the effects of chemical treatment on plant growth were evaluated visually as shown in Table XV.
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§ 2 I · o — u o — u 01 i. ~ Γ> ε 2§ 2 I · o - u o - u 01 i. ~ Γ> ε 2
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ä ? s ,d6 ti ___ - - TT _____ 214 70577ä? s, d6 ti ___ - - TT _____ 214 70577
Kuten seuraavissa tenteissä havaitaan, ovat tämän keksinnön yhdisteet hyödyllisiä tiettujen vesirikkaruohojen torjuntaan.As will be seen in the following exams, the compounds of this invention are useful in controlling certain water weeds.
Yhdisteitä levitettiin kasveille myrkyttömässä liuottimessa suihkeena kauttaaltaan pieniin lammikoihin, jotka sisälsivät vesihy sintin (Eichornia crassipes) taimia, jotka olivat kooltaan ? 5 — 30 cm Testikohteita pidettiin kasvihuoneessa ja arvioinnit kasvit reagoin nista tehtiin 4 viikkoa levityksen jälkeen. Tämä testi kuvaa näiden yhdisteiden hyödyllisyyttä vesirikkaruohojen torjuntaan ja tulokset on esitetty taulukossa XVI.The compounds were applied to the plants in a non-toxic solvent by spraying throughout in small ponds containing seedlings of water hyacinth (Eichornia crassipes) of size? 5 to 30 cm The test subjects were kept in a greenhouse and evaluations of the plants' response were made 4 weeks after application. This test illustrates the utility of these compounds in controlling water weeds and the results are shown in Table XVI.
15 705 7 715 705 7 7
Ί du lukko XVIΊ du lock XVI
Arviot kasvien reagoiunisia Määrä ,,Estimates of plants react to the amount of sleep ,,
Rakenne yR VusilyasJUitUStructure yR VusilyasJUitU
CL /0CH3CL / 0CH3
/-( o N —C/ - (o N —C
/ S~~\\ 11 / \/ S ~~ \\ 11 / \
< ( ) )—SO -NH-C-NH-C CH 1/32 9G<()) —SO -NH-C-NH-C CH 1/32 9G
Y^V ^ / )-' N — C/ cl ^ 0CH3Y ^ V ^ /) - 'N - C / cl ^ OCH3
/^Λ S /°-ch3 1/32 9G2C/ ^ Λ S / ° -ch3 1/32 9G2C
\U >-S°2-NH-C-NH-C C-S ° 2-NH-C-NH-C C
'-( N . CH 1/16 9C'- (N. CH 1/16 9C
CH3CH3
H-C- 0 H.C 1/16 9GH-C- 0 H.C 1/16 9G
3 \ 3\_3 \ 3 \ _
<^G Il \ L/^8 9G<^ G Il \ L / ^ 8 9G
HC C-NH-C-NH-SOrM f ))HC C-NH-C-NH-SOrM f))
Xr — \SV IM 9GACXr - \ SV IM 9GAC
//
H3C 1/2 9G4CH3C 1/2 9G4C
h3co Cl S /M\h3co Cl S / M \
HC C-NH-C-NH-SO^M Γ J y 1/32 9G9CHC C-NH-C-NH-SO 2 M Γ J y 1/32 9G9C
^ czz )-' / / H c' Cl - I! _____ 70577^ czz) - '// H c' Cl - I! _____ 70577
Τ·ιπ1ιιΜ'ο XVIX · ιπ1ιιΜ'ο XVI
Arv i o ( I· a:: v i en rengo j nn i ;·, t.aArv i o (I · a :: v i en Rengo j nn i; ·, t.a
Rakenne Määrä Vesi- _____ kg ai/ha_hyas intiStructure Amount Water _____ kg ai / ha_hyas inti
H_G 0 FH_G 0 F
3 \ \3 \ \
C — N 0 }-v 1/32 9G.1CC - N 0} -v 1/32 9G.1C
H<\ \-NH-C-™-SOr/Q\H <\ \ -NH-C- ™ -SOr / Q \
C— n/ \-' 1/16 9G1CC— n / \ - '1/16 9G1C
/ h3g CH-/ 3/ h3g CH- / 3
ςν q .N — C. 1/32 9Gςν q .N - C. 1/32 9G
II # %II #%
HG C-SO„-NH-C-NH-C CHHG C-SO 2 -NH-C-NH-C CH
Il H 2 \ /Il H 2 \ /
HC-CH XN~ C' 1/16 9GHC-CH XN ~ C '1/16 9G
\ CH3 /CH3\ CH3 / CH3
o N — C 1/32 9G5Co N - C 1/32 9G5C
II # ^II # ^
c εθ,,-NH-C-NH-C N CHc εθ ,, - NH-C-NH-C N CH
/S\ / 2 \ // S \ / 2 \ /
HC C N—C 1/16 9CHC C N-C 1/16 9C
II II \ HC _CH 0-CH3 H C ClII II \ HC _CH 0-CH3 H C Cl
3 \-m 0 \-v 1/32 9G3 \ -m 0 \ -v 1/32 9G
// ^ " //^\\ HC7 C-NH-C-HH-SO^f f J )// ^ "// ^ \\ HC7 C-NH-C-HH-SO ^ f f J)
\C_N/ VT-/ 1/16 9G2C\ C_N / VT- / 1/16 9G2C
h3c// 1 70577h3c // 1 70577
Taulukko XVITable XVI
Arviot kuovien reagoi n n istuEstimates of dryness react n n sit
Rakenne Mauru Vesihyasintti __________kγτ ai/ha___ H_C0 H CO.Structure Mauru Water Hyacinth __________ kγτ ai / ha ___ H_C0 H CO.
3 \ 3 \ C~N 0 /-\3 \ 3 \ C ~ N 0 / - \
// ^ l! /V^A// ^ l! / V ^ A
HC C-NH-C-KH-SO—( ( )) L/32 9GHC C-NH-C-KH-SO— (()) L / 32 9G
\ / V~^Y\ / V ~ ^ Y
CZZN N-( / \ H3C0 0CH3CZZN N- (/ \ H3CO0CH3
Fl /CH3F1 / CH3
/r^\\ n ^ A/ r ^ \\ n ^ A
( f ) }~S0o-NH-C-NH-C CH 1/32 9G(f)} -SO-NH-C-NH-C CH 1/32 9G
X=V xn^c/ \ CH3 - - τ ___ 218 705 77X = V xn ^ c / \ CH3 - - τ ___ 218 705 77
Taulukko XVITable XVI
Arviot kasvien reagoinnisi Määrä Vesihyasintti kg ai/haEstimates of your plant's response Amount Water hyacinth kg ai / ha
Rakenne cu3Structure cu3
,- 0 H-/ 1/32 9G, - 0 H- / 1/32 9G
\/ N—^ 1/16 9G\ / N— ^ 1/16 9G
Cl cu3 /-\ o N .Cl cu3 / - \ o N.
/.11 //.11 /
( ( J V—SO -KH-C-KH-C C-0-CH3 1/32 9G9C((J V — SO -KH-C-KH-C C-O-CH3 1/32 9G9C
' ( \c/'(\ c /
Cl c o-ci-uCl c o-ci-u
JJ
H3C\ h3cqH3C \ h3cq
. C — Hv o )-V. C - Hv o) -V
N C-NH-C-Nn-S02—^ f J \ *1/32 i*GN C-NH-C-Nn-SO 2 - ^ f J \ * 1/32 i * G
\ — H ^ X-/ / \ h3co och3 »3C-°\ / C — N N 0 .-, ^ Η /V~n\\ - H ^ X- / / \ h3co och3 »3C- ° \ / C - N N 0 .-, ^ Η / V ~ n \
K C-HH-C-Nii-SO^-( f )) 3/22 8GK C-HH-C-So-SO 2 - (f)) 3/22 8G
^Cirl/ \-/ / h3c-° H_C0 Cl 3 X \^ Cirl / \ - / / h3c- ° H_C0 Cl 3 X \
c - W 0 )-Vc - W 0) -V
/ \ Il //^λ\ h c-:;;:-c->u:-sor\ ) 1/32 lg&c \ vr_/ / \ U3C 0CH3 219 70577 C l/ \ Il // ^ λ \ h c -: ;;: - c-> u: -sor \) 1/32 lg & c \ vr_ / / \ U3C 0CH3 219 70577 C l
0 \-v 1/32 9G7C0 \ -v 1/32 9G7C
n C-O-C C-ra-C-Ml-SO^/ ( ) )n C-O-C C-ra-C-Ml-SO ^ / ())
3 C, J 2Λ^7 1/16 907C3 C, J 2Λ ^ 7 1/16 907C
! CH3 Käyttö kasvien kasvua säätelevinä aineina Käyttönsä lisäksi, rikkaruohomyrkkyinä kaavan I yhdisteet ovat käyttökelpoisia myös aineina, joilla menestyksellisesti voidaan muunnella valittujen kasvilajien kasvua. Määrät (tavallisesti 0,01 - 1,0 kg/ha) ja levityksen ajoitus valitaan lajin mukaan haluttujen vaikutusten saamiseksi pienimmällä mahdollisella myrkyllisyydellä kasveille. Sekä kasvamis- että lisääntymiskasvua voidaan säädellä. Seuraavissa esitetyt esimerkit kuvaavat sokeriruo’on, hirssin, bahia-ja muiden ruohojen reaktioita tämän keksinnön yhdisteisiin. Sokeri-ruo'ossa ja hirssissä saadaan aikaan "kemiallinen kypsymis"-vaikutus, mistä on seurauksena suurempi liukoisten jähmeiden aineiden (useimmiten sokereiden) saalis. Monissa muissa ruohoissa kasvu ja taimikor-ren kehittyminen rajoittuvat näiden yhdisteiden vaikutuksesta, mikä vähentää liikkumavaatimuksia. Nämä yhdisteet ovat myös käyttökelpoisia puumaisten ja ruohomaisten leveälehtisten kasvien kasvun säätelyyn.! CH3 Use as Plant Growth Regulators In addition to their use as herbicides, the compounds of formula I are also useful as substances that can successfully modify the growth of selected plant species. The amounts (usually 0.01 to 1.0 kg / ha) and the timing of application are selected according to the species to obtain the desired effects with the least possible toxicity to plants. Both growth and reproduction growth can be regulated. The following examples illustrate the reactions of sugar cane, millet, Bahia and other grasses to the compounds of this invention. Sugar cane and millet produce a "chemical ripening" effect, resulting in a higher yield of soluble solids (mostly sugars). In many other herbs, growth and seedling development are limited by these compounds, which reduces movement requirements. These compounds are also useful in regulating the growth of woody and herbaceous broadleaf plants.
Esimerkki AExample A
Kääpiösokeriruokokasveja, 6-8 kuukauden ikäisiä, joissa oli 3-5 vartta (1,5-3 m:n korkuisia) 25 cm"n ruukussa, ruiskutettiin seu-raavassa esitetyillä yhdisteillä (kaksi ruukkua/yhdiste). Jokainen varsi mitattiin korkeimpaan näkyvään lehtituppeen tutkimuksen alussa ja lopussa vaikutuksen määrittämiseksi korkeuden kasvuun. Kun varret korjattiin talteen 5 viikkoa käsitelyn jälkeen, niistä uutettiin mehua jaliukoiset jähmeä! aineet määritettiin jokaisen varren ylä-, keski-ja alakolmanneksen keskustasta. Taulukko XVII osoittaa, että varsissa, joita oli käsitelty tämän keksinnön yhdisteillä, liukoiset jähmeät aineet olivat lisääntyneet ja kasvu oli supistunut verrattuna liuotin-vertailuun (500 1/ha vettä + pinta-aktiivista ainetta Tween 20® 0,2 %).Dwarf sugar cane plants, 6-8 months old, with 3-5 stems (1.5-3 m tall) in a 25 cm "pot were sprayed with the compounds shown below (two pots / compound). Each stem was measured in the highest visible leaf sheath. When the stems were harvested 5 weeks after treatment, juice was extracted from them, and soluble solids were determined from the center of the upper, middle, and lower thirds of each stem.Table XVII shows that stems treated with the compounds of this invention , soluble solids were increased and growth was reduced compared to the solvent control (500 l / ha water + Tween 20® surfactant 0.2%).
220 7 0 5 7 7220 7 0 5 7 7
Taulukko XVIITable XVII
Sokeriruokovarsien osatParts of sugar cane stalks
Kasvu kg/ha (cm) Alaosa Keskiosa YläosaGrowth kg / ha (cm) Bottom Middle Top
Cl o OCH3 0.25 15 18.2 17.6 11.1 /=< " /-ς _ , Ä (v Λ-SO2-NH-C-NKC( CH l.o 9 l8.J 19.0 l4.6 CH3 CK, o ,00¾ 0.25 15 18.1 18.9 15Λ /=< " N-Cv (v .VsOa-NH-C-NHq 'CH 1.0 6 19.9 20.4 15.8 u=c ^¾Cl o OCH3 0.25 15 18.2 17.6 11.1 / = <"/ -ς _, Ä (v Λ-SO2-NH-C-NKC (CH lo 9 l8.J 19.0 l4.6 CH3 CK, o, 00¾ 0.25 15 18.1 18.9 15Λ / = <"N-Cv (v .VsOa-NH-C-NHq 'CH 1.0 6 19.9 20.4 15.8 u = c ^ ¾
Liuotinvertailu 4o 16.7 1^.8 6.1 C1 0 (^DCIl3 0.25 5 I9.9 20.2 I6.8 ^^-so2-nh-c-nh<^ Jft 1.0 4 18.8 19.9 16.6 CHaSolvent comparison 4o 16.7 1 ^ .8 6.1 C1 0 (^ DCIl3 0.25 5 I9.9 20.2 I6.8 ^^ - so2-nh-c-nh <^ Jft 1.0 4 18.8 19.9 16.6 CHa
Esimerkki BExample B
Pieniä makean hirssin taimia, joita kasvatettiin yksi 15 cm:n ruukkua kohti vaiheeseen juuri ennen esiinpuhkeamista, ruiskutettiin seuraavassa esitetyillä yhdisteillä. Silmämääräiset vaikutukset todettiin n. 3 viikkoa ruiskutuksen jälkeen, sitten 4 viikon kuluttua kasvit korjattiin talteen ja liukoiset jähmeät aineet määritettiin ylä-, keski- ja alakolmanneksen keskustassa kussakin korressa. Kuten taulukossa XVIII on esitetty, lisääntyi liukoisten jähmeiden aineidei prosenttiosuus, ja kasvu sekä kukkiminen supistuivat korsissa, jotka oli käsitelty tämän keksinnön yhdisteillä.Small sweet millet seedlings grown one per 15 cm pot to the stage just before emergence were sprayed with the following compounds. Visual effects were observed approximately 3 weeks after spraying, then after 4 weeks, the plants were harvested and soluble solids were determined in the center of the upper, middle, and lower quarters on each stalk. As shown in Table XVIII, the percentage of soluble solids increased, and growth and flowering decreased in straw treated with the compounds of this invention.
72 1 7057772 1 70577
Taulukko XVIIITable XVIII
Liukoisia jähmeitä aineita ilmaistuna %:eina vertailu-arvoista hirssin korren eri osissa_ 3-viikon reagoinnin Keski-Soluble solids expressed as% of reference values in different parts of the millet stalk_ Mean of the 3-week response
Yhdiste kg/ha arvostelu 1 Alaosa ..Compound kg / ha rating 1 Bottom ..
_ ^ _ _ osa Ylaosa 9 £Ha 1.0 9G,F,2X 114 132 69 ^^-SOz-NHC-NH-^ 'CH 4.0 9G,F 115 128 'CHa CHa 9 '°CHa /=< /‘4 0.03 9G, F,5X 119 99 '34_ ^ _ _ part Top 9 £ Ha 1.0 9G, F, 2X 114 132 69 ^^ - SO 2 -NHC-NH- ^ 'CH 4.0 9G, F 115 128' CHa CHa 9 '° CHa / = </' 4 0.03 9G, F, 5X 119 99 '34
4 /VsOs-NHC-NH-q pH4 / VsOs-NHC-NH-q pH
W N=q 0.5 &G,F,3X 119 119 112 CHa 0 pH$ /=\ " 1.0 8G,F,2X 114 l40 96W N = q 0.5 & G, F, 3X 119 119 112 CHa 0 pH $ / = \ "1.0 8G, F, 2X 114 l40 96
ά λ-S 02-NHC-NH-C pHά λ-S 02-NHC-NH-C pH
'n^ch 0 CHa /SN " /"4 0.125 &G,F,1C 119 109 88'n ^ ch 0 CHa / SN "/" 4 0.125 & G, F, 1C 119 109 88
HC C-SOz-HH-C-IIH-Q CHHC C-SO 2 -HH-C-IIH-Q CH
" " 2.0 &G, F 122 115 66 HC-CH CHa S ,0CK3 /-=\ 0.5 9G,F,2X 111 100 57"" 2.0 & G, F 122 115 66 HC-CH CHa S, 0CK3 / - = \ 0.5 9G, F, 2X 111 100 57
4 VsOz-NHC-NH-G^ CH4 VsOz-NHC-NH-G ^ CH
^ 'N OT 2.0 &G,F,2X 118 105 59^ 'N OT 2.0 & G, F, 2X 118 105 59
Cl OCH3 0 ,CHa /=v " ,ΓΤ=<Λ 0.5 7G 115 106 98Cl OCH3 0, CHa / = v ", ΓΤ = <Λ 0.5 7G 115 106 98
φ-SOa-MHC-HH-^ CHφ-SOa-MHC-HH- ^ CH
OCH2CH3 c 0 CHa /=< 0.125 9G,F,1C 139 115 140OCH2CH3 c 0 CHa / = <0.125 9G, F, 1C 139 115 140
4 λ-SOa-NHC-NH-tf CH4 λ-SOa-NHC-NH-tf CH
W 'N=< 0.5 9G, F, 2C 147 129 146 CHa CHa 9 /¾ /=< /-4 0.125 &G,F 113 113 114W 'N = <0.5 9G, F, 2C 147 129 146 CHa CHa 9 / ¾ / = </ -4 0.125 & G, F 113 113 114
4 Λ-soz-imc-mi-ö pH4 Λ-soz-imc-mi-ö pH
' ^=9 0.5 &G,F 120 113 121 CHa CHa _ i; ____ 70577'^ = 9 0.5 & G, F 120 113 121 CHa CHa _ i; ____ 70577
Taulukko XVIIITable XVIII
Liukoisia jäluneita ainei i .Imaistuna o:e.i.na vertai arvoista hirssin korren osissa_ 3-viikon reagoinninSoluble traces of substances i .Assessed o: e.i.na comparable values in parts of millet stalk_ 3-week reaction
Yhdiste k ['/La arvostelu 1 Alaosa eski_ _ _____ osa Y laosa F 0 ,CH3 /=< " 0.125 &G,F,1C 127 127 136Compound k ['/ La rating 1 Lower part eski_ _ _____ part Y part F 0, CH3 / = <"0.125 & G, F, 1C 127 127 136
C >S02-NH-C-NH-<f jCHC> SO2-NH-C-NH- <f jCH
W=cf 0.5 &G,F,1C 127 127 136 CHa 0 pCHa /=\ " /N-i 0.25 &C,F 120 120 121W = cf 0.5 & G, F, 1C 127 127 136 CHa 0 pCHa / = \ "/ N-i 0.25 & C, F 120 120 121
<λ >S0a-NHC-NH-C jCH<λ> SO2-NHC-NH-C jCH
W NN=q 1.0 &G,F 120 120 121 CHa 0 ^OCHa /=\ " 0.25 F 120 113 107W NN = q 1.0 & G, F 120 120 121 CHa 0 ^ OCHa / = \ "0.25 F 120 113 107
d >S02-NHC-NH-q CHd> SO 2 -NHC-NH-q CH
N=(( 1.0 &G, F 113 113 107 OCH3N = ((1.0 & G, F 113 113 107 OCH 3
Cl 0 ,CHa /=< " 0.5 6G,F,2X - 122 - O- S O2 - NHC- NH- c ynCl 0, CHa / = <"0.5 6G, F, 2X - 122 - O- S O2 - NHC- NH- c yn
Cl CH3 0CH3 C /°0¾ /=< 0.125 9C-,F,8X - 130Cl CH 3 OCH 3 C / ° 0¾ / = <0.125 9C-, F, 8X - 130
C 3-SOa-NHC-NH-Q pHC 3 -SO 4 -NHC-NH-Q pH
^ N=C^ N = C
C1 OCH3 ci o CHo /=( " 0.06 9G, F,2X - 139C1 OCH3 ci o CHo / = ("0.06 9G, F, 2X - 139
(^>-S02-NHC-NH-C ,CH(^> - SO 2 -NHC-NH-C, CH
Ii=CHIi = CH
Cl 0 CH3 /=( " /i- 0.06 &G F 2U - 165Cl 0 CH3 / = ("/ i- 0.06 & G F 2U - 165
(n /VSOa-NHC-NH-q CH(n / VSOa-NHC-NH-q CH
W N=cf CH- °-°ö &G, F, IX - I65 <\ /VsOa-NHC-NH-C CH ^W N = cf CH- ° - ° ö & G, F, IX - I65 <\ / VsOa-NHC-NH-C CH ^
^ M^ M
CH3 2 2 3 „ Λ 70577CH3 2 2 3 „Λ 70577
Taulukko XVIIITable XVIII
Liukois La jährncj La ainoita ilmaistuna °&:eina vertailu-arvoista hirssin korren eri osissa_ 3-vi ikon reagoinninSoluble La jährncj La expressed only in ° & as reference values in different parts of the millet stalk_ 3-vi ikon response
Yhckste kg/ha arvostelu 1 Alaosa ' ......Yhckste kg / ha rating 1 Bottom '......
_ _____ osa Ylaosa ci P 0 ,00¾_ _____ part Upper part ci P 0, 00¾
>=< 0.25 0 - 122 -(v ySOa-IiHC-IiH-C CH> = <0.25 0 - 122 - (v ySOa-IiHC-IiH-C CH
^ V< OCHs o DCH3 Q" Jfstd 0.05 &G,F,2X 119 112 116^ V <OCHs o DCH3 Q "Jfstd 0.05 & G, F, 2X 119 112 116
S Oa-NHC-NH-G, ,CHS Oa-NHC-NH-G,, CH
n '»-(f 0.125 &G,F,2X 155 111 105 w C Ha 0.5 &G,F,2X 126 117 108 0 ^ OCH3 0.125 5G,F,2X 116 107 101 <^-so2-nhc-nh-^ n 0.5 8g,f 115 107 115 ÖCHa 2.0 8C-,F 118 107 115 0 pHs 0>125 gG/F/3X 128 125 Il8 /=\ " N-q ^^-'SOa-NHC-NH-^ N 0.5 9G,F 143 124 105 %H3 2.0 9G,F 127 Hl 152 0 PCH3 0.125 &G,F, 1C 127 124 125n '»- (f 0.125 & G, F, 2X 155 111 105 w C Ha 0.5 & G, F, 2X 126 117 108 0 ^ OCH3 0.125 5G, F, 2X 116 107 101 <^ - so2-nhc-nh- ^ n 0.5 8g, f 115 107 115 ÖCHa 2.0 8C-, F 118 107 115 0 pHs 0> 125 gG / F / 3X 128 125 Il8 / = \ "Nq ^^ - 'SOa-NHC-NH- ^ N 0.5 9G, F 143 124 105% H3 2.0 9G, F 127 Hl 152 0 PCH3 0.125 & G, F, 1C 127 124 125
" fl-C"fl-C
{^X-SOs-NHC-NH-C 0.5 &C-,?,2C 120 113 79{^ X-SOs-NHC-NH-C 0.5 & C -,?, 2C 120 113 79
N=CHN = CH
2.0 &G,F,2C 153 120 1142.0 & G, F, 2C 153 120 114
Cfl3__ 1 F *» kukkiminen viivästynyt 22* 70577Cfl3__ 1 F * »flowering delayed 22 * 70577
Esimerkki CExample C
Bahia-ruohon taimia (Paspaium notatum Flugge), jotka olivat hyvin pihjenneet esiin 13 cm:n ruukuissa, ruiskutettiin XIX yhdisteillä, kun siemenpäät juuri olivat valmiina esiinpuhkeamiseen. Kasvit olivat n. 35 cm:n korkuisia ja kolme ruukkua ruiskutettiin yläpäästä C550 1/ha) jokaisella määrällä. Taulukossa XIX esitetty reaktio todettiin 45 päivän kuluttua käsittelystä. Keksinnössä yhdisteet hidastivat kasvua ja tukauttivat siemenpäiden kehittymisen.Seedlings of Bahia grass (Paspaium notatum Flugge), which had well emerged in 13 cm pots, were sprayed with XIX compounds when the seed heads were just ready for emergence. The plants were about 35 cm high and three pots were sprayed from the top (C550 1 / ha) with each amount. The reaction shown in Table XIX was observed 45 days after treatment. In the invention, the compounds slowed growth and inhibited seed head development.
Taulukko XIXTable XIX
45-päivän Siemen-kg/ha reagoinnin päiden arvostelut tukahdutta-mis-% 0.03 2G 10 0 CHa s " ^:-(1 0.125 2G 3045-day Seed-kg / ha response end reviews suppression-% 0.03 2G 10 0 CHa s "^ :-( 1 0.125 2G 30
KC C-SOa-NH-C-IIH-q CHKC C-SOa-NH-C-IIH-q CH
H 11 \=cr 0.5 3G, 2U 90 HC-CK 'CHa 1.0 3G, 2U 100 CHa 0 OCHa 0.008 2G 0 <^>-S02-Iui-C -ΙΓΗ-<ζ CH 0.03 30 30 ^CHa 0.125 90,1C, 2U 95 0.5 9G,2C,2U 95 0.008 2G 70 0 OCHa " n=(^ 0.03 70 70H 11 \ = cr 0.5 3G, 2U 90 HC-CK 'CHa 1.0 3G, 2U 100 CHa 0 OCHa 0.008 2G 0 <^> - SO2-Iui-C -ΙΓΗ- <ζ CH 0.03 30 30 ^ CHa 0.125 90.1C , 2U 95 0.5 9G, 2C, 2U 95 0.008 2G 70 0 OCHa "n = (^ 0.03 70 70
/f^VsOa-HH-C-HH-q CH/ f ^ VsOa-HH-C-HH-q CH
li-C 0.125 &G, 2C,2U 95li-C 0.125 & G, 2C, 2U 95
Cl CHa 0.5 &G,3C, 2U 100 ??5 70577Cl CHa 0.5 & G, 3C, 2U 100 ?? 5 70577
Seuraavat testitulokset esitetään tämän keksinnön yhdisteiden biologisen aktiivisuuden edelleen kuvaamiseksi. Luvut kuvaavat yhdisteiden, jotka ovat selektiivisiä kahden tärkeän viljakasvin, riisin ja vehnän suhteen, rikkaruohojen hävitystehokkuutta.The following test results are presented to further illustrate the biological activity of the compounds of this invention. The figures describe the weed control efficiency of compounds that are selective for two important cereals, rice and wheat.
Testiyhdisteitä levitettiin kasveille myrkyttömässä liuottimes-sa kasvukerroksella täytettyihin ruukkuihin, jotka sisälsivät väli-tuotehybridiriisin, japanilaisen riisin, piharuohon (hehi.noohloa crusgalli) sekä Ipomoea-lajin siemeniä. Erästä yhdistettä levitettiin myös vehnään, hukkakauraan (Avena fatua), Bromus teetorum’iin ja Bromus secalinus'een. Joidenkin tai kaikkien edellä mainittujen lajien esiinpuhjenneet taimet (ilmaantumisen jälkeen) sisällytettiin myös testiin. Kasveja pidettiin kasvihuoneessa ja silmämääräinen arvotelu kasvien reagoinnista tehtiin yleisesti n. 3 viikkoa levityksen jälkeen. Tulokset on esitetty taulukossa XX.Test compounds were applied to the plants in pots filled with a growth layer in a non-toxic solvent containing intermediate hybrid rice, Japanese rice, yard grass (hehi.noohloa crusgalli) and seeds of the species Ipomoea. One compound was also applied to wheat, oats (Avena fatua), Bromus teetorum and Bromus secalinus. Emerging seedlings of some or all of the above species (after emergence) were also included in the test. Plants were kept in a greenhouse and visual evaluation of plant response was generally made approximately 3 weeks after application. The results are shown in Table XX.
__ - TT ________- 226 70577 srurcipoas snuioag O co | uinaoxoox snuioag S? ££ i 5 panp>[p>p(nfj .__ - TT ________- 226 70577 srurcipoas snuioag O co | uinaoxoox snuioag S? ££ i 5 panp> [p> p (nfj.
£__o o ;_ d WUM3A f £ __a_ r xCpT-paanodi o o H no g av av y <5 g •h " o o b o a o£ __o o; _ d WUM3A f £ __a_ r xCpT panel o o H no g av av y <5 g • h "o o b o a o
6 cqonapgTj cv cΛ g VO CV VO6 cqonapgTj cv cΛ g VO CV VO
c Tsxxa uauTPTxupdpp !c Tsxxa uauTPTxupdpp!
Π3 '' · · O O OOΠ3 '' · · O O OO
m--£- e τετταθχοηχτχΡΛm-- £ - e τετταθχοηχτχΡΛ
__ö O__i O__ö O__i O
snirpxpoas snuioag O O | ωηαοχορχ. snuioag O O | ραηρχρνρ^Η u 5 __oS l_ « ^3Λ o h | +-> ----snirpxpoas snuioag O O | ωηαοχορχ. snuioag O O | ραηρχρνρ ^ Η u 5 __oS l_ «^ 3Λ o h | + -> ----
X w τΓρτ DmrrrVfT O O I O OX w τΓρτ DmrrrVfT O O I O O
x -h TLPX-pomoai ^vo t O aO r^\ S ____ o 3 x -μ oqonapnxg o O I aax -h TLPX-pomoai ^ vo t O aO r ^ \ S ____ o 3 x -μ oqonapnxg o O I aa
% VO ON LTV OV% VO ON LTV OV
3 r0 -------- - , , ,3 r0 -------- -,,,
pj 2 xsixa ιΐθίΓΓρχτιΐράρρ O Opj 2 xsixa ιΐθίΓΓρχτιΐράρρ O O
5 * 0aJ i H -H 0 o c ΐ5ΓταθχοηχτχρΑ o m · o av aj -—*- — - —--------- c ριι/τρ Sv oj 5 <<5 * 0aJ i H -H 0 o c ΐ5ΓταθχοηχτχρΑ o m · o av aj -— * - - - —--------- c ριι / τρ Sv oj 5 <<
-- Ή H r-f H- Ή H r-f H
n n n id ir: K O O v /N.n n n id is: K O O v / N.
*r* w-<* r * w- <
g Sg S
0=0 o = o £ £0 = 0 o = o £ £
N OJN OJ
ai O oai O o
•μ H CO rH H CO• μ H CO rH H CO
J o f O o i 1 Ä Ίό)J o f O o i 1 Ä Ίό)
Claims (1)
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US67466876A | 1976-04-07 | 1976-04-07 | |
US67466876 | 1976-04-07 | ||
US76991477A | 1977-02-23 | 1977-02-23 | |
US76991377A | 1977-02-23 | 1977-02-23 | |
US76991377 | 1977-02-23 | ||
US76991477 | 1977-02-23 |
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FI70577C FI70577C (en) | 1986-09-24 |
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BG (4) | BG27720A3 (en) |
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CS (1) | CS208101B2 (en) |
CY (1) | CY1139A (en) |
DK (1) | DK149343C (en) |
EG (1) | EG12883A (en) |
ES (1) | ES457657A1 (en) |
FI (1) | FI70577C (en) |
GR (1) | GR64862B (en) |
HU (1) | HU182948B (en) |
IE (1) | IE44983B1 (en) |
IL (1) | IL51834A (en) |
IT (1) | IT1085563B (en) |
KE (1) | KE3188A (en) |
MT (1) | MTP812B (en) |
NO (1) | NO147951C (en) |
NZ (1) | NZ183821A (en) |
PH (1) | PH14671A (en) |
PT (1) | PT66417B (en) |
RO (1) | RO70577B (en) |
SE (1) | SE436742B (en) |
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RU2623438C1 (en) * | 2016-05-26 | 2017-06-26 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Salts of n,n,n',n'-tetramethylmethandyiamine n1,n1,n4,n4-tetramethyl-2-buthin-1,4-diamine c 3-(6-methyl-4-metoxy-1,3,5-triazinyl-2)-1-(2-chlorophenylsulphonyl)urea, which shows herbicid activity, and the method of their obtaining |
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1977
- 1977-04-05 SU SU772466102A patent/SU860675A3/en active
- 1977-04-05 BR BR7702160A patent/BR7702160A/en unknown
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- 1977-04-06 GR GR53173A patent/GR64862B/en unknown
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- 1977-04-06 IE IE729/77A patent/IE44983B1/en not_active IP Right Cessation
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