DK149343B - SULPHONAMIDE DERIVATIVES, HERBICIDES AND PLANT GROWTH CONTROLLING AGENTS CONTAINING THESE AND PROCEDURES FOR COMBATING WEEDS AND REGULATING PLANT GROWTH - Google Patents

SULPHONAMIDE DERIVATIVES, HERBICIDES AND PLANT GROWTH CONTROLLING AGENTS CONTAINING THESE AND PROCEDURES FOR COMBATING WEEDS AND REGULATING PLANT GROWTH Download PDF

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DK149343B
DK149343B DK153777AA DK153777A DK149343B DK 149343 B DK149343 B DK 149343B DK 153777A A DK153777A A DK 153777AA DK 153777 A DK153777 A DK 153777A DK 149343 B DK149343 B DK 149343B
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methyl
aminocarbonyl
hydrogen
methoxy
island
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DK149343C (en
DK153777A (en
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George Levitt
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Du Pont
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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
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Description

o 1 149343o 1 149343

Den foreliggende opfindelse angår N-(heterocycloamino-carbonyl)arylsulfonamider med plantevækstregulerende og herbicid virkning. Opfindelsen angår endvidere herbicide og plantevækstregulerende midler indeholdende disse forbindel-5 ser samt fremgangsmåder, ved hvilke forbindelserne anven des til bekæmpelse af ukrudt eller regulering af plantevækst.The present invention relates to N- (heterocycloamino-carbonyl) arylsulfonamides having plant growth regulating and herbicidal activity. The invention further relates to herbicidal and plant growth regulators containing these compounds as well as methods by which the compounds are used to control weeds or regulate plant growth.

Fra beskrivelsen til fransk patent nr. 1.468.747 kendes p-substituerede phenylsulfonamider med antidiabetisk virkning og med formlen 10From the specification of French Patent No. 1,468,747 p-substituted phenylsulfonamides having antidiabetic effect and of formula 10 are known.

0 N0 N

R- ^ ^ -S02-NH-C-NH- ^ 15 hvor R betyder hydrogen, halogen, trifliiormethyl eller alkyl.R--SO₂-NH-C-NH-- where R is hydrogen, halogen, trifluoromethyl or alkyl.

Fra Chem.Ab., 53, 18052 g (1959) kendes endvidere visse sulfonamider, herunder uracilderivater med formlen 0Further, from Chem.Ab., 53, 18052 g (1959), certain sulfonamides, including uracil derivatives of formula 0, are known.

20 H3C-^ ^-S02NHCNHR20 H3C- ^ -SO2NHCNHR

N-_ hvor R betyder butyl, phenyl eller -/ \N-where R is butyl, phenyl or -

V“VV "V

25 1 hvor R betyder hydrogen eller methyl. Ved afprøvningen for hypoglykæmisk virkning på rotter (oral dosis på 25 mg/100 -g), har de forbindelser, hvori R betyder butyl og phenyl, kraf-tigst virkning. De andre forbindelser har svag virkning el-30 ler er inaktive.Wherein R is hydrogen or methyl. In the test for hypoglycaemic action in rats (oral dose of 25 mg / 100-g), the compounds in which R is butyl and phenyl have the most potent effect. The other compounds are weak or are inactive.

Fra J.Acta. Polon, Pharm. 19, side 121-125 (1962) (Chem.Ab., 59 1633 e) er det kendt at fremstille N-[(2,6--dimethoxypyrimidin-4-yl) aminocarbonyl]-4-methylbenzen-sulfonamid med formlen 35 0 _<^0CH3 ch3-^ ^-so2nh-c-nh- / \ ^ 0CH3 2 149343 o På baggrund af analogi med en kendt forbindelse forudsiges det, at denne forbindelse har hypoglykasmisk virkning.From J.Acta. Polon, Pharm. 19, pages 121-125 (1962) (Chem. Ab., 59, 1633 e) it is known to prepare N - [(2,6-dimethoxypyrimidin-4-yl) aminocarbonyl] -4-methylbenzene sulfonamide of formula 35 0 _ <^ 0CH3 ch3- ^ -so2nh-c-nh- / \ ^ 0CH3 2 149343 o Based on analogy with a known compound, this compound is predicted to have a hypoglycasmic effect.

Endvidere er det kendt fra beskrivelsen til hollandsk patent nr. 121.788 at fremstille forbindelser med form-5 len (1) med generel eller selektiv herbicid virkningFurthermore, it is known from the specification of Dutch Patent No. 121,788 to prepare compounds of formula (1) having general or selective herbicidal activity

Cl /Q\-S02NHCN-//^f (1) r4 ifCl / Q \ -S02NHCN - // ^ f (1) r4 if

10 R10 R

1 2 hvor R og R hver for sig kan betyde alkyl med 1-4 carbon-3 4 atomer, og R og R hver for sig kan betyde hydrogen, chlor eller alkyl med 1-4 carbonatomer.Wherein R and R may individually represent alkyl of 1-4 carbon-3 4 atoms and R and R individually may be hydrogen, chlorine or alkyl of 1-4 carbon atoms.

15 De her omhandlede forbindelser adskiller sig struk turelt fra de kendte forbindelser ifølge hollandsk patent nr. 121.788 ved, at triazinheterocyclen i de kendte forbindelser er substitueret med en aminogruppe og desuden skal indeholde et chloratom, medens de her omhandlede for-20 bindeiser ikke er begrænset således. Sulfonylurinstofdelen i de her omhandlede forbindelser skal desuden være usubsti-tueret, medens de kendte forbindelser skal være substitueret med en alkylgruppe på denne del.The compounds of this invention differ structurally from the known compounds of Dutch Patent No. 121,788 in that the triazine heterocycle of the known compounds is substituted with an amino group and must furthermore contain a chlorine atom, while the compounds of this invention are not limited. thus. In addition, the sulfonylurea component of the compounds of the present invention must be unsubstituted, while the known compounds must be substituted by an alkyl group on this portion.

Forsøg har vist, at de her omhandlede forbindelser 25 har en kraftigere herbicid virkning end de i det hollandske patentskrift omhandlede, især over for fingeraks og cyperus. Desuden er de her omhandlede forbindelser virkningsfulde selv i små mængder, hvilket miljømæssigt er en fordel.Studies have shown that the compounds of the present invention have a stronger herbicidal effect than those disclosed in the Dutch patent, especially in the case of finger axis and cyperus. In addition, the compounds of this invention are effective even in small quantities, which is an environmental benefit.

Fra J.Drug. Res. 6, 123 (1974) kendes desuden for-30 bindeiserne med formlen A S (2> ^ s/ \ S02NHCNHR 1 hvor R betyder pyridyl. Disse forbindelser kan anvendes som antidiabetika.From J.Drug. Res. 6, 123 (1974), further, the compounds of formula A S (2> s / 2 SO 2 NHCNHR 1 where R is pyridyl) are known. These compounds can be used as antidiabetic agents.

o 3 149343o 3 149343

Tilstedeværelsen af uønsket vegetation forårsager væsentlig beskadigelse af nyttige afgrøder, især landbrugsprodukter, som tilfredsstiller menneskets fundamentale behov for føde og fibre, f.eks. bomuld, ris, majs, 5 hvede, sojabønne og lignende afgrøder. Den nuværende befolkningseksplosion og samtidige globale mangel på fødevarer og fibre nødvendiggør en forøget effektivitet ved fremstillingen af disse afgrøder. Undgåelse eller formindskelse af tab af en del af disse værdifulde afgrøder 10 ved udryddelse eller inhibering af væksten af uønsket vegetation er en måde at forøge denne effektivitet.The presence of undesirable vegetation causes significant damage to useful crops, especially agricultural products, which satisfy the human's basic needs for food and fiber, e.g. cotton, rice, corn, 5 wheat, soybean and similar crops. The current population explosion and the simultaneous global shortage of food and fiber necessitates increased efficiency in the production of these crops. Avoiding or reducing the loss of a portion of these valuable crops 10 by eradicating or inhibiting the growth of undesirable vegetation is one way to increase this efficiency.

Der findes mange forskellige materialer, som kan anvendes til udryddelse eller inhibering af væksten af uønsket vegetation, og sådanne materialer betegnes sædvan-15 ligvis som herbicider. Der er imidlertid et stort behov for mere effektive herbicider, som destruerer eller bekæmper ukrudtsplanter uden at fremkalde væsentlig beskadigelse af de nyttige afgrøder. Nogle ukrudtsarter, specielt cyperus, er meget vanskelige at bekæmpe, og mange 20 af de herbicider, som anvendes til bekæmpelse af cyperus, har så ringe selektivitet, at de fremkalder beskadigelse af afgrøderne selv.There are many different materials that can be used to eradicate or inhibit the growth of undesirable vegetation, and such materials are usually referred to as herbicides. However, there is a great need for more effective herbicides that destroy or control weeds without causing significant damage to the useful crops. Some weed species, especially cyperus, are very difficult to control, and many 20 of the herbicides used to control cyperus have so little selectivity that they cause damage to the crops themselves.

I overensstemmelse med den foreliggende opfindelse tilvejebringes hidtil ukendte forbindelser med formlen I 25 og agrikulturelt egnede salte deraf, egnede agrikulturel- le midler indeholdende disse forbindelser samt fremgangsmåder til anvendelse deraf som selektive samt som generelle herbicider med såvel præemergent som postemergent virkning. Forbindelserne har kraftig herbicid virkning. De er 30 især anvendelige til bekæmpelse af cyperus, idet de kun for årsager minimal beskadigelse af de ønskede afgrøder såsom bomuld, ris, majs, hvede og lignende. De omhandlede forbindelser er ejendommelige ved, at de har den almene formelIn accordance with the present invention, there are provided novel compounds of formula I and agriculturally suitable salts thereof, suitable agricultural agents containing these compounds, and methods of using them as selective as well as general herbicides having both pre-energetic and post-energetic effects. The compounds have strong herbicidal activity. They are particularly useful for the control of cypress, as they cause only minimal damage to the desired crops such as cotton, rice, corn, wheat and the like. The compounds in question are peculiar in that they have the general formula

WW

35 R1-S02-NH-C-NH-R IR 1 -SO 2 -NH-C-NH-R I

hvor 4where 4

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149343 R er x x149343 R is x x

$—f $—S$ —F $ —S

eller -f VNor -f VN

5 - „1 . R er 3 4 RJ li · fQ\· eller 1° e7/\r6 J? Q r® r10 15 3 6 R og R hver for sig betyder hydrogen, fluor, chlor, brom, iod, C^_4 alkyl, alkoxy, nitro, trifluormethyl, cyano, CH,S(0) - eller CH-CH-S(0) -, λ o ii 3 2η R* betyder hydrogen, fluor, chlor, brom eller methyl, 20 R"* betyder hydrogen, fluor, chlor, brom, methyl eller methoxy, 7 R betyder hydrogen, fluor, chlor, brom, C-j^ alky! eller C^_2 alkoxy, g R betyder hydrogen, methyl, chlor eller brom, 9 10 25 R og R hver for sig betyder hydrogen, methyl, chlor eller brom, W og Q hver for sig betyder· oxygen eller svovl, n er 0, 1 eller 2, X betyder hydrogen, chlor, brom, methyl, ethyl, alk- 30 oxy, trifluormethyl, CH^S- eller CH^OCHj-> og Z betyder methyl eller methoxy, samt deres agrikulturelt egnede salte, idet dog når 5 a) R er forskellig fra hydrogen, mindst en af sub-stituenterne R^, R^, R^ og R^ er forskellig fra hydrogen, 35 og mindst to af substituenterne R , R’, R° og R' er hydrogen,5 - "1. R is 3 4 RJ li · fQ \ · or 1 ° e7 / \ r6 J? Q and R 10 15 3 6 R and R respectively are hydrogen, fluoro, chloro, bromo, iodo, C 1-4 alkyl, alkoxy, nitro, trifluoromethyl, cyano, CH, S (O) - or CH-CH-S (0) -, λ o in 3 2η R * means hydrogen, fluorine, chlorine, bromine or methyl, 20 R "* means hydrogen, fluorine, chlorine, bromine, methyl or methoxy, 7 R means hydrogen, fluorine, chlorine, bromine , C1-4 alkyl or C1-2 alkoxy, g R means hydrogen, methyl, chlorine or bromine, R 10 and R each independently represent hydrogen, methyl, chlorine or bromine, W and Q each represent oxygen or sulfur, n is 0, 1 or 2, X means hydrogen, chlorine, bromine, methyl, ethyl, alkoxy, trifluoromethyl, CH 2 S- or CH 2 OCH 2 - and Z means methyl or methoxy, and their agriculturally suitable salts, except that when 5 a) R is different from hydrogen, at least one of the substituents R 1, R 2, R 2 and R 2 is different from hydrogen, 35 and at least two of the substituents R, R ', R R 'is hydrogen,

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5 149343 b) R·* er hydrogen og subs ti tuenterne R^, R4, R6 og 7 R alle er forskellige fra hydrogen, er substituenterne R^, R4, R^ og R7 alle enten chlor eller methyl, og 3 7 c) R og R begge betyder hydrogen, er mindst en af 4 5 6 5 substituenterne R , R eller R hydrogen.B) R · is hydrogen and the subsets of the R R, R R, R6 and R R substituents are all different from hydrogen, the substituents R ^, R4, R ^ and R7 are all either chlorine or methyl, and 37 7 c) R and R both represent hydrogen, at least one of the substituents R, R or R is hydrogen.

Midlerne ifølge opfindelsen er ejendommelige ved, at de indeholder de ovennævnte forbindelser, og fremgangsmåderne ifølge opfindelsen er ejendommelige ved, at forbindelserne påføres vegetationen eller voksestedet.The compositions according to the invention are characterized in that they contain the above-mentioned compounds, and the methods according to the invention are characterized in that the compounds are applied to the vegetation or the growing site.

10 Foretrukne forbindelser på grund af virkning eller pris eller begge dele er forbindelser med formel I som defineret ovenfor, hvori R^" betyder R7 R6 3 og R betyder hydrogen, fluor, chlor, brom, alkyl, 20 Cl-4 alkoxy' CH3S_ eller CH3CH2S-, 5 R betyder hydrogen, fluor, chlor, brom eller methyl, og ø R betyder hydrogen, fluor, chlor, brom, C^_4 alkyl, C1_^ alkoxy, trifluormethyl, nitro, CH^S- eller CH^Cl^S-, 25 idet dog når a) R^ er forskellig fra hydrogen, skal R^, R4, R® 7 og R hver for sig betyde hydrogen, fluor, chlor, brom, methyl eller methoxy, og når R er nævnte pyrimidinylgrup-pey er X methyl eller C^_3 alkoxy, og Z er methyl eller 30 methoxy, eller når R er nævnte triazinylgruppe, er X methyl eller C^_3 alkoxy, og Z er methoxy.Preferred compounds due to effect or cost or both are compounds of formula I as defined above, wherein R 2 represents R 7 R 6 3 and R represents hydrogen, fluoro, chloro, bromo, alkyl, C 1-4 alkoxy 'CH 3 S CH 3 CH 2 S-, 5 R means hydrogen, fluorine, chlorine, bromine or methyl, and island R represents hydrogen, fluorine, chlorine, bromine, C 1-4 alkyl, C 1-4 alkoxy, trifluoromethyl, nitro, CH 2 S- or CH 2 Cl 2 S-, 25 however, when a) R 1 is different from hydrogen, R 2, R 4, R 7 and R must each mean hydrogen, fluoro, chloro, bromo, methyl or methoxy, and when R is said pyrimidinyl group. pey is X methyl or C1-3 alkoxy and Z is methyl or methoxy or when R is said triazinyl group, X is methyl or C3-3 alkoxy and Z is methoxy.

Ligeledes foretrukne forbindelser på grund af virkning eller pris eller begge dele er forbindelser med formlen I som defineret ovenfor, r1 “ /ζ> eiier /Ov R8 ° R9 V» 35 hvor o 6 149343 8 9 10 hvor R , R og R har de ovenfor anførte betydninger, og når R betyder nævnte pyrimidinylgruppe, er Q svovl, X er methyl eller alkoxy, og Z er methyl eller methoxy, eller når R er nævnte triazinylgruppe, er Q svovl, X er 5 methyl eller alkoxy, og Z er methoxy.Also preferred compounds because of effect or price or both are compounds of formula I as defined above, wherein R, R and R have the and R when R is said pyrimidinyl group, Q is sulfur, X is methyl or alkoxy and Z is methyl or methoxy or when R is said triazinyl group, Q is sulfur, X is methyl or alkoxy and Z is methoxy. .

Specielt foretrukne forbindelser på grund af deres udmærkede virkning eller særdeles fordelagtige pris eller begge dele er følgende: 1) N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2- 10 -chlorbenzensulfonamid, smp. 194-196°C, 2) N-1(4,6-dimethoxypyrimidin-2-yl)aminocarbony1]-2,5--dichlorbenzensulfonamid, smp. 189-190°C, 3) N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]--2-methylbenzensulfonamid, smp. 172-174°C, 15 4) N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-thio- phensulfonamid, smp. 224-228°C, 5) N-[(4-methoxy-6-methy1-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorbenzensulfonamid, smp. 174-178°C, 6) N~[ (4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]- 20 -2-chlorbenzensulfonamid, smp. 188-189°C og 7) N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl--2,5-dimethoxybenzensulfonamid, smp. 187-188°C.Particularly preferred compounds because of their excellent effect or extremely advantageous price or both are the following: 1) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-10-chlorobenzene sulfonamide, m.p. 194-196 ° C, 2) N-1 (4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C, 3) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-methylbenzenesulfonamide, m.p. 172-174 ° C, 4) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-thiophenesulfonamide, m.p. 224-228 ° C, 5) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C, 6) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 188-189 ° C and 7) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl-2,5-dimethoxybenzenesulfonamide, m.p. 187-188 ° C.

Selv om alle forbindelserne med formlen I har herbicid virkning, har de ikke alle selektiv virkning på alle 25 afgrøder. Ved valg af den pågældende forbindelse, ukrudts bekæmpelse og afgrøde kan der imidlertid opnås sikkerhed.Although all the compounds of formula I have herbicidal activity, they do not have all selective effect on all 25 crops. However, by selecting the compound concerned, weed control and crop protection can be achieved.

Nogle af forbindelserne har således især selektivitet ved bekæmpelse af ukrudtsarter i hvede og ris, cyperusbekæmpel-se i afgrøder såsom majs, bomuld, sojabønne eller ris, busk-30 bekæmpelse og vandhyacintbekæmpelse. Endvidere kan forbin delserne med formlen I anvendes som plantevækstregulerende midler, f.eks. til at forøge sukkerindholdet i sukkerrør og durra og til at undertrykke frøhoveddannelse (seedhead formation) hos græsser såsom Bahiagræs.Thus, some of the compounds have particular selectivity in controlling weed species in wheat and rice, cyperus control in crops such as maize, cotton, soybean or rice, shrub control and water hyacinth control. Furthermore, the compounds of formula I can be used as plant growth regulators, e.g. to increase the sugar content of sugar cane and sorghum and to suppress seedhead formation in grasses such as Bahia grass.

3535

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7 149343 Særligt foretrukne er: A) Til selektiv bekæmpelse af ukrudt i hvede: 1) N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]--2-chlor-5-methoxybenzensulfonamid, smp. 199-200°C, 5 2) N-[(4-methoxy-6-methyl-l,3,5-triazin-2-yl) aminocarbo nyl]-2-chlorbenzensulf onamid, smp. 174-178°C, 3) N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]-2--chlorbenzensulfonamid, smp. 188-189°C og 4) N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]- 10 -2,5-dimethoxybenzensulfonamid, smp. 187-188°C.Particularly preferred are: A) For selective control of wheat weeds: 1) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide, m.p. 199-200 ° C, 2) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C, 3) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 188-189 ° C and 4) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2,5-dimethoxybenzenesulfonamide, m.p. 187-188 ° C.

B) Til selektiv bekæmpelse af cyperus i afgrøder: 1) N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,5--dichlorbenzensulfonamid, smp. 189-190°C og 15 2) N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,6- -dichlorbenzensulfonamid, smp. 177-182°C.B) For selective control of crops in crops: 1) N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C and 2) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2,6- dichlorobenzenesulfonamide, m.p. 177-182 ° C.

C) Til bekæmpelse af vandhyacinth: 1) N-[4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]- 20 -2-chlorbenzensulfonamid, smp. 194-196°C, 2) N-[(4-methoxy-6-methyl-l,3,5-triazin-2-yl) aminocarbonyl]--2-chlorbenzensulfonamid, smp. 174-178°C, 3) N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]--benzensulfonamid, smp. 183-185°C og 25 4) N-[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)aminocarbonyl]- -2-chlor-5-methoxybenzensulfonamid, smp. 175-176°C.C) To control water hyacinth: 1) N- [4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] - 20 -2-chlorobenzenesulfonamide, m.p. 194-196 ° C, 2) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C, 3) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide, m.p. 183-185 ° C and 4) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide, m.p. 175-176 ° C.

D) Til vækstregulering: 1) N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-benzensulfon- 30 amid, smp. 228-230°C, 2) N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,5-di-chlorbenzensulfonamid, smp. 189-190°C, 3) N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]--benzensulfonamid, smp. 183-185°C, 35 8D) For growth regulation: 1) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide, m.p. 228-230 ° C, 2) N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C, 3) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide, m.p. 183-185 ° C, 8

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149343 4) N- [(4-methoxy-6-methyl-l,3,5-triazin-2-y1)aminocarbonyl] -benzensulfonamid, 5) N-[(4,6-dimethyl-l,3,5-triazin-2-yl)aminocarbonyl]--benzensulfonamid, smp. 200-201°C og 5 6) N- [(4-methoxy-6-methyl-l,3,5-triazin-2-yl) aminocar bonyl ]-2-chlorbenzensulf onamid, smp. 174-178°C.4) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -benzenesulfonamide, 5) N - [(4,6-dimethyl-1,3,5-methyl) triazin-2-yl) aminocarbonyl] benzenesulfonamide, m.p. 200-201 ° C and 5 6) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C.

E) Til selektiv ukrudtsbekæmpelse i ris: 1) N-[(4-methylpyrimidin-2-yl)aminocarbonyl]-2-chlorbenzen- 10 sulfonamid, smp. 201-203°C og 2) N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,5-di-brombenzensulfonamid, smp. 201-204°C.E) For selective weed control in rice: 1) N - [(4-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzene sulfonamide, m.p. 201-203 ° C and 2) N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dibromobenzenesulfonamide, m.p. 201-204 ° C.

F) Til selektiv buskbekaanpelse; 15 N-1(4,6-dimethoxy-l,3,5-triazin-2-yl) aminocarbonyl]-benzen sulf onamid, smp. 183-185°C.F) For selective shrub cover; N-1 (4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide, m.p. 183-185 ° C.

Som illustreret i nedenstående reaktionsskema 1 kan forbindelserne med formlen I fremstilles ved at omsætte et passende 2-aminopyrimidin eller 2-amino-l,3,5-triazin med 20 formlen III med et passende substitueret sulfonylisocyanat eller -isothiocyanat med formlen II, hvor R1, W, X, Z og R har de ovenfor angivne betydninger.As illustrated in Scheme 1 below, the compounds of formula I can be prepared by reacting an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine of formula III with an appropriately substituted sulfonyl isocyanate or isothiocyanate of formula II wherein R 1 , W, X, Z and R have the above meanings.

Reaktionsskema 1.Scheme 1.

25 W25 W

r1so2ncw + nh2-r -> r1so2nhcnh-r (II) (III) (I) 30 Omsætningen gennemføres bedst i et indifferent aprotisk organisk opløsningsmiddel såsom methylenchlorid, tetrahydro-furan eller acetonitril ved atmosfæretryk og stuetemperatur. Tilsætningsmåden er ikke kritisk. Det er imidlertid ofte hensigtsmæssigt at sætte sulfonylisocyanatet eller -iso- 35The reaction is best carried out in an inert aprotic organic solvent such as methylene chloride, tetrahydrofuran or acetonitrile at atmospheric pressure and room temperature. The method of addition is not critical. However, it is often convenient to add the sulfonyl isocyanate or iso-

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9 149343 thiocyanatet til en omrørt suspension af aminen med formlen III. Da sådanne isocyanater og isothiocyanater sædvanligvis er væsker, kan deres tilsætning let reguleres.The thiocyanate for a stirred suspension of the amine of formula III. Since such isocyanates and isothiocyanates are usually liquids, their addition can be readily regulated.

Omsætningen er sædvanligvis eksoterm. I nogle til-5 fælde er det ønskede produkt uopløseligt i det varme reak tionsmedium og udkrystalliserer derfra i ren form. Produkter, som er opløselige i reaktionsmediet, isoleres ved fordampning af opløsningsmidlet, triturering af den faste remanens med et opløsningsmiddel såsom 1-chlorbutan eller 10 ethylether og filtrering.The turnover is usually exothermic. In some cases, the desired product is insoluble in the hot reaction medium and crystallizes from it in pure form. Products which are soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with a solvent such as 1-chlorobutane or 10 ethyl ether and filtration.

I visse tilfælde vil det være muligt at fremstille et isomerprodukt ved den i reaktionsskema 1 viste reaktion. Sådanne isomerprodukter kan dannes ved addition af forbindelsen II til de endocycliske nitrogenatomer i aminen 15 III og har den nedenfor eksemplificerede struktur:In some cases, it is possible to prepare an isomer product by the reaction shown in Scheme 1. Such isomer products can be formed by adding compound II to the endocyclic nitrogen atoms in amine 15 III and having the structure exemplified below:

w\N «V Mw \ N «V M

R-'-SO^HC-]^ ^-X , R1SQ2NHC—^ ^-ZR -'- SO ^ HC -] ^^ -X, R1SQ2NHC— ^^ -Z

Z "Xr 20 eller * Ψ r1-so9nhc-n^n 25 z-AA'xZ "Xr 20 or * Ψ r1-so9nhc-n ^ n 25 z-AA'x

De som udgangsmaterialer anvendte sulfonylisocyanater med formlen II (hvor W betyder 0) kan fremstilles ved at omsætte tilsvarende sulfonamider med phosgen i nærværelse af 30 n-butylisocyanat under tilbagesvaling i et opløsningsmiddel såsom chlorbenzen under anvendelse af fremgangsmåden ifølge H. Ulrich og A.A.Y. Sayigh, Newer Methods of Preparative Organic Chemistry, bind VI, side 223-241, Academic Press,The sulfonyl isocyanates of formula II (where W means 0) can be prepared by reacting similar sulfonamides with phosgene in the presence of reflux n-butyl isocyanate in a solvent such as chlorobenzene using the method of H. Ulrich and A.A.Y. Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, pages 223-241, Academic Press,

New York og London, W. Foerst Ed. I tilfælde, hvor det 35 o 10 149343 ønskede sulfonylisocyanat dannes i ringe udbytte ved anvendelse af ovenstående fremgangsmåde, kan sulfonylurin-stof dannet ved omsætning af butylisooyanat med det passende sulfonamid omsættes med phosgen som beskrevet i 5 ovenstående reference.New York and London, W. Foerst Ed. In cases where the desired sulfonyl isocyanate is formed in poor yield using the above process, sulfonylurea substance formed by reaction of butyl isoyanate with the appropriate sulfonamide can be reacted with phosgene as described in the above reference.

Fremstillingen af sulfonamiderne ud fra ammoniumhydroxid og sulfonylchlorider er vidt beskrevet i litteraturen, jfr. f.eks. Crossley et al., J.Am.Chem.Soc.The preparation of the sulfonamides from ammonium hydroxide and sulfonyl chlorides is widely described in the literature, cf. eg. Crossley et al., J.Am.Chem.Soc.

60, 2223 (1938). Fremstillingen af 2-furansulfonamid er 10 beskrevet i J. Org. Chem. 18 894 (1953).60, 2223 (1938). The preparation of 2-furanesulfonamide is described in J. Org. Chem. 18 894 (1953).

Visse sulfonylchlorider fremstilles bedst ved chlor-sulfonering af et substitueret benzen, naphthalen eller thiophen i carbontetrachlorid under anvendelse af fremgangsmåden ifølge H.T. Clarke et al., Org. Synth. Coll.Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene, naphthalene or thiophene in carbon tetrachloride using the method of H.T. Clarke et al., Org. Synth. Coll.

15 bind 1, 2. udgave, 1941, side 85. Andre benzensulfonyl-chlorider fremstilles bedst ved diazotering af det passende anilin med natriumnitrit i saltsyre efterfulgt af omsætning af diazoniumsaltet med svovldioxid og cuprochlo-rid i eddikesyre under anvendelse af fremgangsmåden ifølge 20 H.L. Yale og F. Sowinski, J. Org. Chem. 25, 1824 (1960).15 Vol. 1, 2nd Edition, 1941, page 85. Other benzenesulfonyl chlorides are best prepared by diazotizing the appropriate aniline with sodium nitrite in hydrochloric acid followed by reaction of the diazonium salt with sulfur dioxide and cuprochloride in acetic acid using the procedure of 20 H.L. Yale and F. Sowinski, J. Org. Chem. 25, 1824 (1960).

Furansulfonylchlorider fremstilles bedst som vist i nedenstående reaktionsskema 2.Furanesulfonyl chlorides are best prepared as shown in Reaction Scheme 2 below.

Kea kt ion s s kema 2.Kea kt ion s s schema 2.

25 - Et„0 - SO« - O +η-Εηω —» 0'Li^ 3° C12 £>30,01 h2o/hci 35 o 14934325 - A + 0 - SO + - O + η-Εηω - »0'Li ^ 3 ° C12 £> 30.01 h2o / hci 35 o 149343

Sulfonylisothiocyanater kan fremstilles ved behandling af sulfonamider med carbondisulfid og kaliumhydroxid efterfulgt af omsætning af dikaliumsaltet med phosgen i overensstemmelse med fremgangsmåden ifølge K. Hartke, Arch.Sulfonyl isothiocyanates can be prepared by treating sulfonamides with carbon disulfide and potassium hydroxide, followed by reaction of the dipotassium salt with phosgene according to the method of K. Hartke, Arch.

5 Pharm., 299, 174 (1966).Pharm., 299, 174 (1966).

Syntesen af heterocycliske aminderivater er beskrevet i "The Chemistry of Heterocyclic Compounds", udgivet af Interscience Publ., New York og London. 2-Aminopyrimidin-erne er beskrevet af D.J. Brown i "The Pyrimidines", bind 10 XVI i ovennævnte værk.The synthesis of heterocyclic amine derivatives is described in "The Chemistry of Heterocyclic Compounds", published by Interscience Publ., New York and London. The 2-aminopyrimidines are described by D.J. Brown in "The Pyrimidines", Volume 10 XVI in the above work.

Agrikulturelt egnede salte af forbindelserne med formlen I er også anvendelige herbicider og kan fremstilles på mange forskellige kendte måder. Eksempelvis kan metalsalte fremstilles ved at behandle forbindelser med formlen I med 15 en opløsning af et alkalimetal- eller jordalkalimetalsalt med en tilstrækkelig basisk anion, f.eks. et hydroxid, alkoxid, carbonat eller hydrid. Kvaternære ammoniumsalte kan fremstilles på tilsvarende måde.Agri-culturally suitable salts of the compounds of formula I are also useful herbicides and can be prepared in a variety of known ways. For example, metal salts can be prepared by treating compounds of formula I with a solution of an alkali metal or alkaline earth metal salt with a sufficient basic anion, e.g. a hydroxide, alkoxide, carbonate or hydride. Quaternary ammonium salts can be prepared in a similar manner.

Salte af forbindelserne med formlen I kan også frem-20 stilles ved udbytning af en kation med en anden. Kation- bytning kan gennemføres ved direkte behandling af en vandig opløsning af et salt af en forbindelse med formlen I, f.eks. et alkalimetalsalt eller kvaternært aminsalt, med en opløsning indeholdende kationen, som skal udbyttes. Denne frem-25 gangsmåde er mest effektiv, når det ønskede salt indehold ende den udbyttede kation er uopløseligt i vand og kan isoleres ved filtrering.Salts of the compounds of formula I can also be prepared by exchanging one cation with another. Cation exchange can be effected by directly treating an aqueous solution of a salt of a compound of formula I, e.g. an alkali metal salt or quaternary amine salt, with a solution containing the cation to be exchanged. This process is most effective when the desired salt containing end of the exchanged cation is insoluble in water and can be isolated by filtration.

Udbytningen kan også gennemføres ved at lede en vandig opløsning af et salt af en forbindelse med formlen I, 30 f.eks. et alkalimetalsalt eller et kvaternært ammonium salt, gennem en søjle pakket med en kationbytterharpiks indeholdende kationen, som skal udbyttes. Ved denne fremgangsmåde udbyttes kationen i harpiksen med kationen i det oprindelige salt, og det ønskede produkt elueres fra søjlen.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 salt or a quaternary ammonium salt, through a column packed with a cation exchange resin containing the cation to be exchanged. In this process, the cation in the resin is exchanged with the cation in the original salt and the desired product is eluted from the column.

35 Denne fremgangsmåde er særlig anvendelig, når det ønskede salt er vandopløseligt.This process is particularly useful when the desired salt is water-soluble.

OISLAND

12 16934312 169343

Syreadditionssalte, som kan anvendes ved den foreliggende opfindelse, kan fås ved at omsatte en forbindelse med formlen I med en egnet syre, f.eks. p-tcbluensulfon-syre, trichloreddikesyre eller lignende syrer.Acid addition salts which can be used in the present invention can be obtained by reacting a compound of formula I with a suitable acid, e.g. p-tcbuenesulfonic acid, trichloroacetic acid or similar acids.

5 Forbindelserne ifølge opfindelsen samt deres frem stilling illustreres nærmere i de følgende eksempler, hvori alle temperaturer er angivet i °C.The compounds of the invention as well as their preparation are further illustrated in the following examples wherein all temperatures are given in ° C.

Eksempel 1 10 N-[(4,6-Dimethylpyrimidin—2-yl)aminocarbonyllbenzensulfonamidExample 1 N - [(4,6-Dimethylpyrimidin-2-yl) aminocarbonylbenzenesulfonamide

Til en tør, grundig omrørt opløsning af 12,4 g 2-amino--4,6-dimethylpyrimidin i 250 ml methylenchlorid ved stuetemperatur og atmosfæretryk sættes dråbevis 18,3 g benzen-sulfonylisocyanat. Den fremkomne blanding omrøres i 2 ti-15 mer, hvorefter det udfældede produkt frafiltreres. Efter vask- ning med 1-chlorbutan smelter produktet ved 228-230°C og har karakteristiske absorptionsbånd i IR-spektret ved 1710, 1620 og 1550 cm Produktet er N-[(4,6-dimethylpyrimidin--2-yl)aminocarbonyl]benzensulfonamid.To a dry, thoroughly stirred solution of 12.4 g of 2-amino-4,6-dimethylpyrimidine in 250 ml of methylene chloride at room temperature and atmospheric pressure is added dropwise 18.3 g of benzene sulfonyl isocyanate. The resulting mixture is stirred for 2 hours, after which the precipitated product is filtered off. After washing with 1-chlorobutane, the product melts at 228-230 ° C and has characteristic absorption bands in the IR spectrum at 1710, 1620 and 1550 cm. The product is N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide.

2020

Eksempel 2 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2- -chlorbenzensulfonamid_Example 2 N - [(4-Methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2- chlorobenzenesulfonamide

Til en suspension af 280 g 2-amino-4-methoxy-6-methyl-25 pyrimidin i 2000 ml methylenchlorid sættes 434 g 2-chlor- benzensulfonylisocyanat under omrøring. Den fremkomne blanding omrør'es i 16 timer, afkøles til 10° og filtreres, hvorved fås 470 g af et fast stof med smp. 195-196°. Massespektrograf isk analyse viser, at produktet har en molekylvægt 30 på 356.To a suspension of 280 g of 2-amino-4-methoxy-6-methyl-pyrimidine in 2000 ml of methylene chloride is added 434 g of 2-chlorobenzenesulfonyl isocyanate with stirring. The resulting mixture is stirred for 16 hours, cooled to 10 ° and filtered to give 470 g of a solid, m.p. 195-196 °. Mass spectrographic analysis shows that the product has a molecular weight of 306.

Analyse for C-^H^CINO^O^SAnalysis for C- HH ^CINO ^O ^S

Beregnet: C 43,89% H 3,40% N 15,75%Calculated: C 43.89% H 3.40% N 15.75%

Fundet: C 43,47% H 3,56% N 15,30% 35 Dette produkt er N-(4-methoxy-6-methylpyrimidin-2- -yl)aminocarbonyl]-2-chlorbenzensulfonamid.Found: C 43.47% H 3.56% N 15.30% This product is N- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide.

OISLAND

13 U934313 U9343

Ved delvis inddampning af filtratet udfældes 20 g biprodukt med smp. 160-162°. IR-spektret for dette biprodukt svarer til IR-spektret for det første bundfald, og produktet har en molekylvægt på 356.By partial evaporation of the filtrate, 20 g of by-product is precipitated with m.p. 160-162 °. The IR spectrum of this by-product corresponds to the IR spectrum of the first precipitate and the product has a molecular weight of 356.

5 Analyse for C13H13C1N0404S:Analysis for C13H13C1N0404S:

Beregnet: C 43,89% H 3,40% N 15,75%Calculated: C 43.89% H 3.40% N 15.75%

Fundet: C 44,09% H 3,56% N 14,97% 10 Ved anvendelse af en ækvivalent mængde af et egnet 2-aminopyrimidin og et passende substitueret benzensulfo-nylisocyanat kan følgende forbindelser med formlen I fremstilles under anvendelse af den i eksempel 1 og 2 beskrevne fremgangsmåde: 15 20 25 1 35 14 149343 R6 R7 CH, • 5 >-<" " 3 r3—// Vso2-nhcnh-/ \ R4 R3 'Ch3 ___r4 r5_R^_R^_Smp. i °C (d) = sønderdeling Η Η Η Η H 228-230 F Η Η Η H 218-219 CH3 Η Η Η H 195-196Found: C 44.09% H 3.56% N 14.97% 10 Using an equivalent amount of a suitable 2-aminopyrimidine and a suitably substituted benzenesulfonyl isocyanate, the following compounds of Formula I can be prepared using the 1 and 2 described methods: 15 20 25 1 35 14 149343 R6 R7 CH, • 5> - <"" 3 r3 - // Vso2-nhcnh- / \ R4 R3 'Ch3 ___r4 r5_R ^ _R ^ _Smp. in ° C (d) = decomposition Η Η Η Η H 228-230 F Η Η Η H 218-219 CH3 Η Η Η H 195-196

Cl Η Η Η H 204-205 Η Η H N02 H 193-196 Η Η H CF3 H 183 (d) H Cl Η Η H 142-143 -CF3 Η Η Η H 218-220 CH30- H CH3°" H H 198-199 CH3 Η H N02 H 191-192 CH3 H ' H -CH(CH3)2 H 157-160 CH3 Η H Cl H 209-211Cl 4 Η Η H 204-205 Η Η H N02 H 193-196 Η Η H CF3 H 183 (d) H Cl Η Η H 142-143 -CF3 Η Η Η H 218-220 CH30- H CH3 ° "HH 198 -199 CH3 Η H N02 H 191-192 CH3 H 'H -CH (CH3) 2 H 157-160 CH3 Η H Cl H 209-211

Cl Η H CH3 H 211-213 F Η H F H 189-190 CH3 Η H CH3 H 193-194Cl Η H CH3 H 211-213 F Η H F H 189-190 CH3 Η H CH3 H 193-194

Cl Η Η H CH3 230-232 N02 H Cl Η H 210-212Cl Η Η H CH3 230-232 N02 H Cl Η H 210-212

Cl Η Η H Cl 177-182 F Η Η H F 208-211Cl Η Η H Cl 177-182 F Η Η H F 208-211

Cl Cl Cl Η H 215-217Cl Cl Cl Η H 215-217

Cl H Cl Cl H 204-205 -CH(CH3)2 H Cl -CH(CH3)2 H 131-136 CH3 H CH3 H CH3 227-231(d) F H F H F 173-180Cl H Cl Cl H 204-205 -CH (CH3) 2 H Cl -CH (CH3) 2 H 131-136 CH3 H CH3 H CH3 227-231 (d) F H F H F 173-180

Cl H Cl H Cl 208-210 CH30- H CH30- H CH30- 192-193Cl H Cl H Cl 208-210 CH30- H CH30- H CH30- 192-193

Cl Cl H Cl Cl 220-222 CH3 CH3 H CH3 CH3 244-246Cl Cl H Cl Cl 220-222 CH3 CH3 H CH3 CH3 244-246

Cl Cl Η Η H 195-197Cl Cl Η Η H 195-197

Cl CH3 Η Η H 196-199 15 149343 _R^_R^_R^_R^_R^_Smp. i °C (d) - sgnderdellng CH30- Cl Η Η H 179-180 F Cl Η Η H 196-197 CH3 Cl Η Η H 208-209Cl CH3 Η Η H 196-199 15 149343 _R ^ _R ^ _R ^ _R ^ _R ^ _Smp. in ° C (d) - Specification CH30- Cl Η Η H 179-180 F Cl Η Η H 196-197 CH3 Cl Η Η H 208-209

Cl H Cl Η H 202-205 F H Cl Η H 202-203 H Cl Cl Η H 210-212 H Cl H Cl H 199-202 CH30 H Cl CH30 H 202-203 F Η H CH3 H 210-212 CH3 Η H F H 200-201Cl H Cl Η H 202-205 FH Cl Η H 202-203 H Cl Cl Η H 210-212 H Cl H Cl H 199-202 CH30 H Cl CH30 H 202-203 F Η H CH3 H 210-212 CH3 Η HFH 200-201

Cl Η H ch3°- H 198-199Cl Η H ch3 ° - H 198-199

Br Η H Br H 211-212 CH30- Η H CH3°- h 193-195 CH3 Η H CH3 H 204-205 CH3 Η H Br H 205-207 C2H50- Η H C2H50- H 208-210 CH30- Η H F H 199-201Br Η H Br H 211-212 CH30- Η H CH3 ° - h 193-195 CH3 Η H CH3 H 204-205 CH3 Η H Br H 205-207 C2H50- Η H C2H50- H 208-210 CH30- Η HFH 199 -201

Cl Η H Cl H 212-213 CH3CH2CH20 Η H CH3CH2CH20 H 150-152 CH30- Η H Cl H 209-210 CH3 CH3 H N02 H 221-223 16 149343Cl Η H Cl H 212-213 CH3CH2CH20 Η H CH3CH2CH20 H 150-152 CH30- Η H Cl H 209-210 CH3 CH3 H N02 H 221-223 16 149343

Tabel I-BTable I-B

Ri R7 n OCHRi R7 n AND

ςΝ_/ ° N_-^ 3 R -// \ -SO „NHCNH-(/ \\ΝΝ_ / ° N _- ^ 3 R - // \ -SO „NHCNH - (/ \\

W/ nWW / nW

R4^V ^CH3R4 ^ V ^ CH3

r3 R4 R5 R6 R7 Smp. i °Cr3 R4 R5 R6 R7 Mp. in ° C

Η Η Η Η H 204-205 H CH3 Η Η H 149-15120 Η Η Η H 204-205 H CH3 Η Η H 149-151

Br Η Η Η H 210-211 F Η Η Η H 198-199 CHjO Η Η Η H 178-180 CH3 Η Η Η H 172-174 -S02CH3 Η Η Η H 170-171 H Cl Η Η H 151-153 Η Η H CF3 H 150-152Br Η Η Η H 210-211 F Η Η Η H 198-199 CHjO Η Η Η H 178-180 CH3 Η Η Η H 172-174 -S02CH3 Η Η Η H 170-171 H Cl Η Η H 151-153 Η Η H CF3 H 150-152

Cl Cl Η Η H 199-200Cl Cl Η Η H 199-200

Cl CH3 Η Η H 177-186 CH30- Cl Η Η H 190-193 CH3 Cl Η Η H 190-192 F Cl Η Η H 193-195 H Cl Cl Η H 193-195 n-C4HgO- Η H n-C4H90- H 182-183 F H Cl Η H 206-208 NO 2 H H Η H 223-225 CF3 H H Η H 194-197Cl CH3 Η Η H 177-186 CH30- Cl Η Η H 190-193 CH3 Cl Η Η H 190-192 F Cl Η Η H 193-195 H Cl Cl Η H 193-195 n-C4HgO- Η H n-C4H90 - H 182-183 FH Cl Η H 206-208 NO 2 HH Η H 223-225 CF3 HH Η H 194-197

Cl H F H H 199-201Cl H F H H 199-201

Cl H Cl Η H 195-197- CH3 Cl H Cl H 187-189 CH30 H CH30 Η H . 182-184 Η H CH30 N02 H 211-213 H Cl H Cl H 207-211 H CH3 CH3 Η H 193-196 F Η H F H 177-178 CH30- Η H Cl H 199-200 CH3 Η H Cl H 206-207 17 149343 __R^_R^_R^_Smp. i °C_Cl H Cl Η H 195-197- CH3 Cl H Cl H 187-189 CH30 H CH30 Η H. 182-184 Η H CH30 N02 H 211-213 H Cl H Cl H 207-211 H CH3 CH3 Η H 193-196 F Η HFH 177-178 CH30- Η H Cl H 199-200 CH3 Η H Cl H 206-207 17 149343 __R ^ _R ^ _R ^ _Smp. i ° C_

CoHc0- Η H ¢,,11-0- H 175-177 2 5 2 bCoHc0- Η H ¢ ,, 11-0- H 175-177 2 5 2 b

Cl Η H CH3 H 197-200 CH3 Η H N02 H 194-195 CH3 Η H -CH(CH3)2 H 136-142Cl Η H CH3 H 197-200 CH3 Η H N02 H 194-195 CH3 Η H -CH (CH3) 2 H 136-142

Cl Η H N02 H 178-180 CH3 Η H CH3 H 174-176 CH3 Η H Br H 195-197Cl Η H N02 H 178-180 CH3 Η H CH3 H 174-176 CH3 Η H Br H 195-197

Br Η H Br H 207-209 CH30- Η H CH30- H 175-177Br Η H Br H 207-209 CH30- Η H CH30- H 175-177

Cl Η H Cl H 174-179 F Η H CH3 H 207-208 CH3 Η H F H 173-175Cl Η H Cl H 174-179 F Η H CH3 H 207-208 CH3 Η H F H 173-175

Cl Η H CH3°- H 199-200 CH30- Η H CH3 H 180-182 F Η Η H F 192-195Cl Η H CH3 ° - H 199-200 CH30- Η H CH3 H 180-182 F Η Η H F 192-195

Cl Η Η H Cl 148-153Cl Η Η H Cl 148-153

Cl Η Η H CH3 166-17 0 CH3S- Η Η Η H 200-202 C2H50- Η H Cl H 180-183 CH30 H Cl CH30 H 173-175 CH3CH2CH20 . Η H CH3CH2CH20 H 173-175 CH-jS Η H Cl H 215-216 CH3 CH3 H N02 H 191-193Cl Η Η H CH3 166-17 0 CH3S- Η Η Η H 200-202 C2H50- Η H Cl H 180-183 CH30 H Cl CH30 H 173-175 CH3CH2CH20. 17 H CH3CH2CH20 H 173-175 CH-jS Η H Cl H 215-216 CH3 CH3 H N02 H 191-193

Cl Cl Cl Η H 186-187Cl Cl Cl Η H 186-187

Cl H Cl Cl H 189-190 CH3 H CH3 H CH3 203-205 F H F H F 197-199Cl H Cl Cl H 189-190 CH3 H CH3 H CH3 203-205 F H F H F 197-199

Cl H Cl H Cl 181-186 CH30- H CH3°- H CH3° 185-187Cl H Cl H Cl 181-186 CH30- H CH3 ° - H CH3 ° 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 N02 H 182-183

Tabel I-CTable I-C

18 149343 :‘v/ : f-F*18 149343: "v /: f-F *

ΈΓ-μ '\-S02NHCNH-/r AΈΓ-μ '\ -S02NHCNH- / r A

R4^ \3 N NOCH3 _R^_R^_R3__R^_Snip, i °C _ Η Η Η Η H 202-203 F Η Η Η H 200-201R4 ^ \ 3 N NOCH3 _R ^ _R ^ _R3__R ^ _ Snip, i ° C _ Η Η Η Η H 202-203 F Η Η Η H 200-201

Cl Η Η Η H 179-181 CH3 Η Η Η H 184-186 H Cl Η Η H >250 Η Η H CF3 H 190-191 F H H H F 213-215Cl -1 Η Η H 179-181 CH3 Η Η Η H 184-186 H Cl Η Η H> 250 Η Η H CF3 H 190-191 F H H H F 213-215

Cl Η Η H Cl 192-194 NO 2 H Cl Η H 196-198 NO 2 Η Η Η H 219-220 CH3S Η H Cl H 211-213 CH30- Cl Η Η H 183-184 F Cl Η Η H 244-245 F H Cl Η H 223-224Cl Η Η H Cl 192-194 NO 2 H Cl Η H 196-198 NO 2 Η Η Η H 219-220 CH3S Η H Cl H 211-213 CH30- Cl Η Η H 183-184 F Cl Η Η H 244- 245 FH Cl Η H 223-224

Cl H F Η H 203-205Cl H F Η H 203-205

Cl H Cl Η H 190-191 CH30- H CH30 Η H 182-184 CH30- Η H CH3 H 227-229Cl H Cl Η H 190-191 CH30- H CH30 Η H 182-184 CH30- Η H CH3 H 227-229

Cl Η H CF3 H 161-162 F Η H F H 210-212Cl Η H CF3 H 161-162 F Η H F H 210-212

Br Η H Br H 201-204 CH30- Η H ch3°- h 198-199 CH3 Η H Br H 170-172Br Η H Br H 201-204 CH30- Η H ch3 ° - h 198-199 CH3 Η H Br H 170-172

Cl Η H N02 H 225-228Cl Η H N02 H 225-228

Cl Η H CH3°~ h 180-181 C3H?0- Η H C3H7° h 188-189 n-C^HgO- Η , H n-C4H90- H 165-167 C~H_0- Η H C0H,-0- H 181-183 CH30- Η H F H 192-194 CH30- Η H Cl H 197-198 19 149343 __R^__Smp. i °C_Cl Η H CH3 ° ~ h 180-181 C3H? 0- Η H C3H7 ° h 188-189 nC ^ HgO- Η, H n-C4H90- H 165-167 C ~ H_0- Η H C0H, -0- H 181 -183 CH30- Η HFH 192-194 CH30- Η H Cl H 197-198 19 149343 __R ^ __ Mp. i ° C_

Cl Η H Cl H 189-190 CH3 Η H Cl H 181-183Cl Η H Cl H 189-190 CH3 Η H Cl H 181-183

Cl Η H CH3 H 216-217 CH3 Η H N02 H 205-207 CH3 Η H -CH(CH3)2 H 110-116 CH3 Η H CH3 H 187-189 CH30- H ch3°- Η H 173-175 CH30 Η Η Η H 193-195 CH30 H Cl CH30 H 141-143 CH3 Cl H Cl H 186-189 (CH3)2CH Η H (CH3)2CH H 161-163 CH3S Η Η Η H 211-214 Η H CH30 N02 H 210-212Cl Η H CH3 H 216-217 CH3 Η H N02 H 205-207 CH3 Η H -CH (CH3) 2 H 110-116 CH3 Η H CH3 H 187-189 CH30- H ch3 ° - Η H 173-175 CH30 Η 19 Η H 193-195 CH30 H Cl CH30 H 141-143 CH3 Cl H Cl H 186-189 (CH3) 2CH Η H (CH3) 2CH H 161-163 CH3S Η Η Η H 211-214 Η H CH30 N02 H 210 -212

Cl Η Η H CH3 171-174 CH3 H CH3 H CH3 197-198 F H F H F 219-221Cl Η Η H CH3 171-174 CH3 H CH3 H CH3 197-198 F H F H F 219-221

Cl H Cl H Cl 194-195 CH30- H CH3°- H CH3°~ 180-181Cl H Cl H Cl 194-195 CH30- H CH3 ° - H CH3 ° ~ 180-181

Cl Cl H Cl Cl 223-224 CH3 CH3 H CH3 CH3 182-184 CF3 Η Η Η H 219-220 CH30 Cl H Cl H 183-185 CH3 Cl H N02 H 207-209 CH3 CH3 H N02 H 225-227Cl Cl H Cl Cl 223-224 CH3 CH3 H CH3 CH3 182-184 CF3 Η Η Η H 219-220 CH30 Cl H Cl H 183-185 CH3 Cl H N02 H 207-209 CH3 CH3 H N02 H 225-227

Tabel I-DTable I-D

20 149343 R6 R7 :wr 2 n_^ch3 r5-\ 7-S02NCNH“{f / _rHs° _20 149343 R6 R7: wr 2 n_ ^ ch3 r5- \ 7-SO2NCNH “{f / _rHs ° _

R3 R4 R5 R6 R7 X Smp. i °CR3 R4 R5 R6 R7 X Mp. in ° C

__(d) = sønderdeling_ H H H H HH 187-189 CH3 Η Η Η H -CH2OCH3 157-158__ (d) = decomposition_ H H H H HH 187-189 CH3 Η Η Η H -CH2OCH3 157-158

Cl H H Η H -CH2OCH3 179-180Cl H H Η H -CH2OCH3 179-180

Cl Η H Cl H -CH2OCH3 174-176 CH30- Η H CH3O- H -CH2OCH3 155-157 F Η Η Η Η H 192-193 CH3 Η Η Η Η H 211-213Cl Η H Cl H -CH2OCH3 174-176 CH30- Η H CH3O- H -CH2OCH3 155-157 F Η Η Η Η H 192-193 CH3 Η Η Η Η H 211-213

Cl Η Η H HH 201-203 H Cl Η H HH 198-199 F Cl H H H H 219-220 CH3 Cl Η Η Η H 211-213 F H Cl H HH 222-235 (d) H Cl H Cl Η H 201-203 CH30- Η H Cl Η H 224-226Cl Η Η H HH 201-203 H Cl Η H HH 198-199 F Cl HHHH 219-220 CH3 Cl Η Η Η H 211-213 FH Cl H HH 222-235 (d) H Cl H Cl Η H 201-203 CH30- Η H Cl Η H 224-226

Cl H H Cl Η H 207-209 CH3 Η H Cl Η H 217-219 F Η H F HH 173-199Cl H H Cl Η H 207-209 CH3 Η H Cl Η H 217-219 F Η H F HH 173-199

Cl Η Η H Cl H 160-163 Η Η Η Η H C2H5°“ 180-182 Η Η Η Η H (CH3)2CHO- 116-120 Η H H H H Cl 213-215 H Cl Η Η H Cl 194-195 Η Η Η Η H CH 3S- 208(d) Η Η Η Η H -CF3 179-182 CH3 Η Η Η H -CF3 172-174Cl Η Η H Cl H 160-163 Η Η Η H C2H5 ° “180-182 Η Η Η Η H (CH3) 2CHO- 116-120 Η HHHH Cl 213-215 H Cl Η Η H Cl 194-195 Η Η Η Η H CH 3S- 208 (d) Η Η Η Η H -CF3 179-182 CH3 Η Η Η H -CF3 172-174

Cl Η Η Η H -CF3 173-175 Η Η H -CF3 H -CF3 160-163 N02 Η Η Η H Cl 170-172Cl Η Η Η H -CF3 173-175 Η Η H -CF3 H -CF3 160-163 N02 Η Η Η H Cl 170-172

Tabel I-ETable I-E

21 149343 R6 R7 0 °ΰΗ3 r5“ \ Vso2nhchh- $ \ r4>Ke3 -<s21 149343 R6 R7 0 ° ΰΗ3 r5 “\ Vso2nhchh- $ \ r4> Ke3 - <s

R3 R4 R5 R6 R7 X Smp. i °CR3 R4 R5 R6 R7 X Mp. in ° C

_(d) = sønderdeling_ Η Η Η Η Η H 199-200 (d) Η Η Η Η H Cl 181-183_ (d) = decomposition_ Η Η Η Η Η H 199-200 (d) Η Η Η Η H Cl 181-183

Cl Η Η Η H Cl 185-188 CH3 Η Η Η H Cl 176-178 Η Η Η Η H CH3S“ 194-196 Η Η Η Η H -CF3 164-168Cl 185 Η Η H Cl 185-188 CH3 Η Η H Cl 176-178 Η Η Η CH H CH3S “194-196 Η Η Η Η H-CF3 164-168

Cl Η Η :.H H -CF3 204-208 CH3 Η Η Η H -CF3 171-173 Η Η H -CF3 H -CF3 191-194 Η Η Η Η H C2H5° 163-165Cl Η Η: .H H -CF3 204-208 CH3 Η Η Η H -CF3 171-173 Η Η H -CF3 H -CF3 191-194 Η Η Η Η H C2H5 ° 163-165

Cl Η Η Η H C2H5° 142-144 CH3 Η Η Η H C2H5°" 148-149 22Cl Η Η Η H C2H5 ° 142-144 CH3 Η Η Η H C2H5 ° 148-149 22

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149343149343

Eksempel 3 N-[(4,6-dimethylpyr imidin-2-y1)aminocarbonyl]-2-thiophensul- fonamid_;__Example 3 N - [(4,6-Dimethylpyrimidin-2-yl) aminocarbonyl] -2-thiophenesulfonamide

Til 12 g 2-amino-4,6-dimethylpyr imidin i 250 ml aceto-5 nitril sættes under omrøring 19 g 2-thiophensulfonylisocyanat.To 12 g of 2-amino-4,6-dimethylpyr imidine in 250 ml of acetonitrile is added with stirring 19 g of 2-thiophenesulfonylisocyanate.

Den fremkomne blanding omrøres i 2 timer og filtreres, hvorved fås det ønskede faste produkt med smp. 215-216°. IR-spek-tret fra dette produkt viser absorptionstoppe ved 1540, 1605 og 1700 cm-1.The resulting mixture is stirred for 2 hours and filtered to give the desired solid product, m.p. 215-216 °. The IR spectrum of this product shows absorption peaks at 1540, 1605 and 1700 cm -1.

1010

Eksempel 4 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,5-dichlor- -3—thiophensulfonamid_Example 4 N - [(4,6-Dimethylpyrimidin-2-yl) aminocarbonyl] -2,5-dichloro--3-thiophenesulfonamide

Til en suspension af 12 g 2-amino-4,6-dimethylpyri-15 midin i 300 liter methylenchlorid sættes ved stuetemperatur 26 g 2,5-dichlor-3-thiophensulfonylisocyanat. Efter omrøring i 16 timer inddampes opløsningen til tørhed, og det ønskede produkt fås som en fast remanens, som tritureres med ethylether, hvorpå der filtreres. Det således fremkomne faste 20 produkt smelter ved 192-194° og har IR-absorptionstoppe ved 1550, 1605 og 1690 cm-1.To a suspension of 12 g of 2-amino-4,6-dimethylpyrimidine in 300 liters of methylene chloride is added at room temperature 26 g of 2,5-dichloro-3-thiophenesulfonylisocyanate. After stirring for 16 hours, the solution is evaporated to dryness and the desired product is obtained as a solid residue which is triturated with ethyl ether and filtered. The solid product thus obtained melts at 192-194 ° and has IR absorption peaks at 1550, 1605 and 1690 cm -1.

Eksempel 5 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-furan- 25 sulfonamid_Example 5 N - [(4-Methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-furanesulfonamide

Til en opløsning af 2,10 g 2-furansulfonylisocyanat i 40 ml methylenchlorid sættes 1,60 g 2-amino-4-methoxy-6--methylpyrimidin. Den fremkomne blanding omrøres i 1 time ved stuetemperatur og tilbagesvales derpå i 15 minutter, 30 hvorefter opløsningsmidlet fjernes under vakuum. Det frem komne faste stof henstilles under ethylether indeholdende spor af acetonitril i 1 dag, hvorefter der filtreres og tørres, hvorved fås det ønskede produkt med smp. 185-188° (sønderdeling).To a solution of 2.10 g of 2-furanesulfonyl isocyanate in 40 ml of methylene chloride is added 1.60 g of 2-amino-4-methoxy-6-methylpyrimidine. The resulting mixture is stirred for 1 hour at room temperature and then refluxed for 15 minutes, after which the solvent is removed under vacuum. The resulting solid was placed under ethyl ether containing traces of acetonitrile for 1 day, then filtered and dried to give the desired product, m.p. 185-188 ° (dec.).

35 2335 23

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Ved anvendelse af en ækvivalent mængde af et passende 2-aminopyrimidin og et passende substitueret thiophen- eller furansulfonylisocyanat, kan de nedenfor i tabel II anførte forbindelser fremstilles under anvendelse af de i eksempel 5 3-5 anførte fremgangsmåder.Using an equivalent amount of an appropriate 2-aminopyrimidine and an appropriately substituted thiophene or furanesulfonyl isocyanate, the compounds listed below in Table II can be prepared using the procedures set forth in Examples 5 to 3.

Tabel II-ATable II-A

1010

XX

—SO„NHC-NH—Z' \y-H-SO "NHC-NH-Z" -y-H

r8/\q/ 11=/ 15 _Q X_Z_Smp. i °C_ H S CH3 CH30- 207-208 H S CH3O- CH30- 206-207 20 Cl S CH3 CH30- 186-187r8 / \ q / 11 = / 15 _Q X_Z_Smp. i ° C_ H S CH3 CH30- 207-208 H S CH3O- CH30- 206-207 20 Cl S CH3 CH30- 186-187

Cl S CH3 CH3 198-199Cl S CH3 CH3 198-199

Cl S H CH3 197-198 H O CH3 CH30 185-188Cl S H CH3 197-198 H O CH3 CH30 185-188

25 Tabel II-BTable II-B

λ x " 3—λ x "3—

S 02NHCNH- / \\ -HS 02NHCNH- / \\ -H

- R9_R10 1_X_Z_Smp. i °C_- R9_R10 1_X_Z_Smp. i ° C_

Cl Cl CH, CH,0- 186-188 35 ^ 3Cl Cl CH, CH, 0- 186-188 35 ^ 3

Cl Cl CH30- CH30- 201-202 U9343 24Cl Cl CH30- CH30- 201-202 U9343 24

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Eksempel 6 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-naphthalen- sulfonamid__Example 6 N - [(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide

Til en suspension af 15,6 g 2-amino-4,6-dimethoxy-5 pyrimidin i 400 ml acetonitril sættes 23,3 g 1-naphthalen- sulfonylisocyanat under omrøring. Efter fortsat omrøring i 14 timer frafiltreres det ønskede faste produkt, som efter vaskning med en lille smule ethylether smelter ved 177-178°.To a suspension of 15.6 g of 2-amino-4,6-dimethoxy-pyrimidine in 400 ml of acetonitrile is added 23.3 g of 1-naphthalenesulfonylisocyanate with stirring. After continued stirring for 14 hours, the desired solid product is filtered off, which after washing with a small amount of ethyl ether melts at 177-178 °.

Ved anvendelse af en ækvivalent mængde af et passende 10 2-aminopyrimidin og 1-naphthalensulfonylisocyanat kan neden stående forbindelser med formlen I fremstilles under anvendelse af den i eksempel 6 beskrevne fremgangsmåde:Using an equivalent amount of a suitable 10-aminopyrimidine and 1-naphthalenesulfonyl isocyanate, the following compounds of formula I can be prepared using the procedure described in Example 6:

N-[(4-chlor-6-methylpyrimidin-2-yl)aminocarbonyl]-15 -1-naphthalensulfonamid, smp. 205-207°CN - [(4-chloro-6-methylpyrimidin-2-yl) aminocarbonyl] -15 -1-naphthalenesulfonamide, m.p. 205-207 ° C

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1--naphthalensulfonamid, smp. 201-202°C N-[(4-methylpyrimidin-2-yl) aminocarbonyl]-1-naphthalensulfonamid, smp. 182-183°CN - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 201-202 ° C N - [(4-methylpyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 182-183 ° C

20 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]- -1-naphthalensulfonamid, smp. 210-211°C N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1--naphthalensulfonamid, smp. 177-178°C. 1 2 3 4 5 6 7 8 9 10 11N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 210-211 ° C N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 177-178 ° C. 1 2 3 4 5 6 7 8 9 10 11

Eksempel 7 2 N-[(4,6-dimethylpyrimidin-2-yl)aminothioxomethyl]benzen- 3 sulfonamid_ 4Example 7 2 N - [(4,6-Dimethylpyrimidin-2-yl) aminothioxomethyl] benzenesulfonamide

Til en tør suspension af 12,4 g 2-amino-4,6-dimethyl- 5 pyrimidin i 60 ml acetonitril sættes 19,9 g benzensulfonyl- 6 isothiocyanat. Det dannede tunge hvide bundfald frafiltreres 7 og vaskes med vandfri ethylether. Produktet har smp. 165- 8 -170° og er N- [ (4,6-dimethylpyrimidin-2-yl)aminothioxomethyl]- 9 benzensulfonamid.To a dry suspension of 12.4 g of 2-amino-4,6-dimethyl-pyrimidine in 60 ml of acetonitrile is added 19.9 g of benzenesulfonyl-6-isothiocyanate. The heavy white precipitate formed is filtered off 7 and washed with anhydrous ethyl ether. The product has m.p. 165-8 -170 ° and is N- [(4,6-dimethylpyrimidin-2-yl) aminothioxomethyl] - 9 benzenesulfonamide.

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Ved anvendelse af en ækvivalent mængde af det passende 11 sulfonylisothiocyanat og et passende substitueret aminopyri- midin kan de i nedenstående tabel III anførte forbindelser 25 149343By using an equivalent amount of the appropriate 11 sulfonyl isothiocyanate and an appropriately substituted aminopyridine, the compounds listed in Table III below may be used.

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fremstilles under anvendelse af fremgangsmåden ifølge eksempel 7:is prepared using the method of Example 7:

5 Tabel III-ATable III-A

R7 ο XR7 ο X

Λ-π N-/ R -// Xy-SO NHC-NH-// \> 10 r4^^r3 R3 R4 R5 R6 R7 X Z_Smp. i °C_ Η Η Η Η H CH3 CH30- 188-189 15 Η Η Η Η H CH30 CH30 192-193Λ-π N- / R - // Xy-SO NHC-NH - // \> 10 r4 ^^ r3 R3 R4 R5 R6 R7 X Z_Smp. i ° C_ Η Η Η Η H CH3 CH30- 188-189 15 Η Η Η Η H CH30 CH30 192-193

Cl Η Η Η H CH3 CH30- 184-185Cl Η Η Η H CH3 CH30- 184-185

Cl Η Η Η H CH30- CH30- 169-172 CH3 H H H H CH3 CH30 165-167 CH3 Η Η Η H CH30- CH30- 181-182 20 CH3°" h h CH3°" H CH3 CH3°“ 178-180 CH30- Η H CH30- H CH30-' CH30- 191-193Cl Η Η Η H CH30- CH30- 169-172 CH3 HHHH CH3 CH30 165-167 CH3 Η Η Η H CH30- CH30- 181-182 20 CH3 ° "hh CH3 °" H CH3 CH3 ° “178-180 CH30- Η H CH30- H CH30- 'CH30- 191-193

Tabel III-B 25Table III-B 25

S XS X

„ N S' // -SO-NHCNH- (/ vv r8As/ 2 30 _X_Z_Smp. i °C_ H CH3 ch3°- 196-197 H CH30- CH30- 202-204 35 26 149343"N S '// -SO-NHCNH- (/ vv r8As / 2 30 _X_Z_Smp. I ° C_ H CH3 ch3 ° - 196-197 H CH30-CH30-202-204 35 26 149343

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Eksempel 8 2-FuransulfonylisocyanatExample 8 2-Furanesulfonyl isocyanate

. O Ov ^ <fY. O Ov ^ <fY

\o / Δ ^°'\l "30 ^0X\S02Li 10 Cl2 /~\ NH4°H /t~\ overskud (C0C1) 2 H20' HC1 ’ XoA.so.ci-^' \»A ^ S02NH2 15 /“\ \ o / ^ u so2nco A. Lithium-2-furansulfinat 20\ o / Δ ^ ° '\ l "30 ^ 0X \ S02Li 10 Cl2 / ~ \ NH4 ° H / t ~ \ excess (C0C1) 2 H20' HC1 'XoA.so.ci- ^' \» A ^ S02NH2 15 A. lithium-2-furanesulfinate 20

Til en opløsning af 39,6 g furan (585 mmol) i 200 ml vandfri ethylether sættes forsigtigt under en nitrogenatmosfære 400 ml 1,6 M n-butyllithium i hexan, idet reaktionstemperaturen holdes på 30° eller derunder. Blandingen om-25 røres, indtil der er sket fuldstændig udfældning. Efter afkøling til -25 til -30° ledes langsomt overskud af gasformigt svovldioxid gennem blandingen i løbet af 2 timer. Blandingen omrøres ved stuetemperatur i yderligere 90 minutter, og det udfældede lithium-2-furansulfinat frafiltreres og 30 vaskes med acetone.To a solution of 39.6 g of furan (585 mmol) in 200 ml of anhydrous ethyl ether is carefully added under a nitrogen atmosphere 400 ml of 1.6 M n-butyllithium in hexane keeping the reaction temperature at 30 ° or less. The mixture is stirred until complete precipitation has occurred. After cooling to -25 to -30 °, excess gaseous sulfur dioxide is slowly passed through the mixture over 2 hours. The mixture is stirred at room temperature for a further 90 minutes and the precipitated lithium-2-furanesulfinate is filtered off and washed with acetone.

Smp. 250°C. IR (nujol) 3400-3000 cm"1 (W), 1700 cm"1, 1550 cm-1 (VW), 1210 cm"1, 1140 cm"1, 1115 cm"1 (m), 1020 cm"1 (VS), 910 cm"1, 880 cm"1, 825 cm"1 (W), 735 cm"1 (S).Mp. 250 ° C. IR (nujol) 3400-3000 cm "1 (W), 1700 cm" 1, 1550 cm -1 (VW), 1210 cm "1, 1140 cm" 1, 1115 cm "1 (m), 1020 cm" 1 ( VS), 910 cm "1, 880 cm" 1, 825 cm "1 (W), 735 cm" 1 (S).

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27 B. 2-Furansulfonylchlorid 90 ml vand, 410 ml koncentreret saltsyre og 68,0 g lithium-2-furansulfinat omrøres og afkøles til 10-15°.27 B. 2-Furanesulfonyl chloride 90 ml of water, 410 ml of concentrated hydrochloric acid and 68.0 g of lithium-2-furanesulfinate are stirred and cooled to 10-15 °.

12,3 ml (39,4 g) flydende chlor tilsættes dråbevis i løbet 5 af 30 minutter. Blandingen omrøres i yderligere 30 minut ter ved 5°, hældes på is og ekstraheres med methylenchlo-rid. Ved fordampning af methylenchloridet fås 44 g 2-fu-ransulfonylchlorid med kp. 95° ved 7 mm Hg.12.3 ml (39.4 g) of liquid chlorine are added dropwise over 5 of 30 minutes. The mixture is stirred for an additional 30 minutes at 5 °, poured on ice and extracted with methylene chloride. Evaporation of the methylene chloride gives 44 g of 2-furansulfonyl chloride with b.p. 95 ° at 7 mm Hg.

IR (ren) 3400 (m), 3120, 1800, 1550 (m), 1450 (S), 10 1380 (VS), 1210, 1160, 1120 (VS), 1035 (m), 1010 (VS), 913, 882 (S).IR (pure) 3400 (m), 3120, 1800, 1550 (m), 1450 (S), 1380 (US), 1210, 1160, 1120 (US), 1035 (m), 1010 (US), 913, 882 (S).

C. 2-Furansulfonamid 23 g 2-Furansulfonylchlorid (138 mmol) sættes dråbe-15 vis til 200 ml koncentreret NH^OH ved 0-5°. Efter omrøring natten over ved stuetemperatur fjernes vandet under vakuum, og bundfaldet vaskes med isvand og tørres. Udbyttes 14 g 2-furansulfonamid.C. 2-Furanesulfonamide 23 g of 2-Furanesulfonyl chloride (138 mmol) is added dropwise to 200 ml of concentrated NH 2 OH at 0-5 °. After stirring overnight at room temperature, the water is removed in vacuo and the precipitate is washed with ice water and dried. Yield 14 g of 2-furanesulfonamide.

Smp. 120-122°C. (litteratur smp. 120-122°C: 20 JOC 18, 894 (1953)). IR (nujol) 3250 cm-1, 3100 cm-1, 1600 cm-1 (W), 1550 cm-1, 1310 cm-1, 1190 cm"1, 1140 cm"1, 1120 cm"1, 1055 cm"1, 1005 cm"1, 930 cm"1, 880 cm"1, 843 cm"1 (S). 1 2 3 4 5 6 35 D. 2-Furansulfonylisocyanat 2 150 ml tør toluen, 25 ml oxalylchlorid (295 mmol) 3 og en spormængde diazabicyclo[2.2.2]octan (DABCO) opvarmes 4 til 90°. 10 g 2-furansulfonamid tilsættes i løbet af 15 mi 5 nutter, og blandingen holdes ved 95° i 2 timer. Efter fil- 6 trering fjernes opløsningsmidlet under vakuum, hvorved fås 2,1 g af en olie, som udviser den karakteristiske isocya-natabsorption i IR-spektret (2280 cm 1).Mp. 120-122 ° C. (literature mp 120-122 ° C: 20 JOC 18, 894 (1953)). IR (nujol) 3250 cm-1, 3100 cm-1, 1600 cm-1 (W), 1550 cm-1, 1310 cm-1, 1190 cm "1, 1140 cm" 1, 1120 cm "1, 1055 cm" 1, 1005 cm "1, 930 cm" 1, 880 cm "1, 843 cm" 1 (S). 1 2 3 4 5 6 35 D. 2-Furanesulfonyl isocyanate 2 150 ml of dry toluene, 25 ml of oxalyl chloride (295 mmol) 3 and a trace amount of diazabicyclo [2.2.2] octane (DABCO) are heated 4 to 90 °. 10 g of 2-furanesulfonamide are added over 15 ml of 5 nuts and the mixture is kept at 95 ° for 2 hours. After filtration, the solvent is removed in vacuo to give 2.1 g of an oil exhibiting the characteristic isocyanate absorption in the IR spectrum (2280 cm 1).

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Eksempel 9 N-[(4,6-Dimethyl-l,3,5-triazin-2-yl)aminocarbonyl]-2-methyl- benzensulfonamid_- _Example 9 N - [(4,6-Dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-methylbenzenesulfonamide

Til 12,3 g 2-amino-4,6-dimethyl-l,3,5-triazin i 250 ml 5 tør acetonitril sættes under omrøring 19,7 g 2-methylbenzen- sulfonylisocyanat med en sådan hastighed, at der undgås kraftig opvarmning af reaktionsblandingen. Omrøringen fortsættes, indtil det ønskede produkt krystalliserer. Produktet frafiltre-res, vaskes med en lille smule ethylether og tørres. Der fås 10 N-[(4,6-dimethyl-l,3,5-triazin-2-yl)aminocarbonyl]-2-methyl- benzensulfonamid med smp. 141-145°C.To 12.3 g of 2-amino-4,6-dimethyl-1,3,5-triazine in 250 ml of dry acetonitrile is added, with stirring, 19.7 g of 2-methylbenzenesulfonylisocyanate at a rate to avoid vigorous heating. of the reaction mixture. Stirring is continued until the desired product crystallizes. The product is filtered off, washed with a small amount of ethyl ether and dried. 10 N - [(4,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-methylbenzenesulfonamide is obtained, m.p. 141-145 ° C.

Eksempel 10 N- [ (4,6-Dimethyl-l,3,5-triazin-2-yl)aminocarbonyl]-2-chlor- 15 benzensulfonamid_Example 10 N- [(4,6-Dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide

Til 12,3 g 2-amino-4,6-dimethyl-l,3,5-triazin i 200 ml acetonitril sættes under omrøring 21,7 g 2-chlorbenzensulfonyl-isocyanat. Alt det faste stof går i opløsning, efter at reagenserne er tilsat, og blandingen inddampes derpå til tørhed.To 12.3 g of 2-amino-4,6-dimethyl-1,3,5-triazine in 200 ml of acetonitrile is added with stirring 21.7 g of 2-chlorobenzenesulfonyl isocyanate. All the solid dissolves after the reagents are added and the mixture is then evaporated to dryness.

20 Den faste remanens tritureres med ethylether og frafilteres, hvorved der fås urent N-[(4,6-dimethyl-l,3,5-triazin-2-yl)-aminocarbonyl]-2-chlorbenzensulfonamid, smp. 115-118°C. NMR--absorptionsspektret for dette produkt i trifluoreddikesyre viser en singlet med 2,69 og 2.9 ppm.The solid residue is triturated with ethyl ether and filtered to give crude N - [(4,6-dimethyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 115-118 ° C. The NMR absorption spectrum of this product in trifluoroacetic acid shows a singlet of 2.69 and 2.9 ppm.

2525

Eksempel 11 N-[(4,6-Dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]-2-chlor- benzensulfonamid__Example 11 N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide

Til 15,6 g 2-amino-4,6-dimethoxy-l,3,5-triazin i 300 ml 30 tør methylenchlorid indeholdende 0,1 g 1,4-diazabicyclo- [2.2.2]octan sættes 21 g 2-chlorbenzensulfonylisocyanat under omrøring. Blandingen omrøres i 16 timer, og det dannede faste stof frafiltreres. Efter vaskning af det faste stof med 1-chlorbutan fås det resulterende produkt, N-[(4,6-dimethoxy-35 -1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorbenzensulfonamid 29To 15.6 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 300 ml of dry methylene chloride containing 0.1 g of 1,4-diazabicyclo [2.2.2] octane is added 21 g of 2- chlorobenzene sulfonyl isocyanate with stirring. The mixture is stirred for 16 hours and the solid formed is filtered off. After washing the solid with 1-chlorobutane, the resulting product, N - [(4,6-dimethoxy-35-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide is obtained.

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149363 med smp. 188-189°C. IR-absorptionsanalyse visér absorptionstoppe ved 1740, 1630 og 1595 cm hvilket er typisk for denne type forbindelse.149363 with m.p. 188-189 ° C. IR absorption analysis shows absorption peaks at 1740, 1630 and 1595 cm which is typical of this type of compound.

Ved at anvende den i eksempel 9-11 beskrevne frem-5 gangsmåde med en ækvivalent mængde af det passende aminotria- zin og det passende substituerede sulfonylisocyanat, kan de nedenfor i tabel IV angivne forbindelser fremstilles:By using the procedure described in Examples 9-11 with an equivalent amount of the appropriate aminotriazine and the appropriately substituted sulfonyl isocyanate, the compounds listed below in Table IV can be prepared:

Tabel IV-ATable IV-A

10 __ ° N_/10 __ ° N_ /

^y-S02NHCNH-^ S^ y-SO2NHCNH- ^ S

^Z^ Z

1515

X Z Smp. i °CX Z Mp. in ° C

CH3 CH3 200-201 CH30 CH30 183-185 20 CH30 CH3 166-171 CH3CH2CH20 CH30 121-124 CH3S CH30 197-199CH3 CH3 200-201 CH30 CH30 183-185 20 CH30 CH3 166-171 CH3CH2CH20 CH30 121-124 CH3S CH30 197-199

Tabel IV-B 25 0 „_/x Q-SO-NHCNH-/'n 3 »=<Table IV-B 25 0 "_ / x Q-SO-NHCNH - / a 3" = <

R·3 ^ ZR · 3 ^ Z

R? X Z Smp. i °CR? X Z Mp. in ° C

CH3 CH30 CH3 158-162 35 CH3 CH30 CH30 144-147 CH3 CH3OCH2 CH3 147-150CH3 CH30 CH3 158-162 35 CH3 CH30 CH30 144-147 CH3 CH3OCH2 CH3 147-150

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149343149343

3Q3Q

X Z Smp. i °CX Z Mp. in ° C

CH3 CH3S CH30 191-193CH3 CH3S CH30 191-193

Cl CH3 CH3 185-187Cl CH3 CH3 185-187

Cl CH30 CH3 174-178 5 Cl CH30 CH30 188-189Cl CH30 CH3 174-178 5 Cl CH30 CH30 188-189

Cl CH3OCH2 CH3 142-145Cl CH3OCH2 CH3 142-145

Cl CH3CH20 CH3 117-121Cl CH3CH20 CH3 117-121

Cl CH3CH20 CH30 132-133 F CH30 CH3 168-172 10 F CH30 CH30 169-175 CF3 CK3 CH3 172-174 CF3 CH3 CH30 165-167 CF3 CH30 CH30 171-173 N02 CH3 CH30 178-181 (sønderdeling) 15 N02 CH30 CH30 175-178 F CH3CH2 CH3 168-170 N02 CH3 CH3 105-110 CH3S CH30 CH3 181-184 CH3S CH30 CH30 171-174 20Cl CH3CH20 CH30 132-133 F CH30 CH3 168-172 10 F CH30 CH30 169-175 CF3 CK3 CH3 172-174 CF3 CH3 CH30 165-167 CF3 CH30 CH30 171-173 N02 CH3 CH30 178-181 (decomposition) 15 N02 CH30 CH30 175-178 F CH3CH2 CH3 168-170 N02 CH3 CH3 105-110 CH3S CH30 CH3 181-184 CH3S CH30 CH30 171-174 20

Tabel IV-CTable IV-C

o N_/1 25 // -SO-NHCNH- W \=K- 35o N_ / 1 25 // -SO-NHCNH- W \ = K- 35

Z Smp. i °CZ Mp. in ° C

Cl CH, CH, 190-191 30 ^ J v.Cl CH, CH, 190-191 30 ^ J v.

Cl CH30 CH30 >250 CF3 CH3 CH3 158-162 CH3 CH3 CH3 184 (størkner) CH3 CH30 CH30 174 (størkner)Cl CH30 CH30> 250 CF3 CH3 CH3 158-162 CH3 CH3 CH3 184 (solidifies) CH3 CH30 CH30 174 (solidifies)

JJ

Tabel IV-DTable IV-D

3131

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XX

5 y n Jjl—5 y n Jjl—

/ Q \-S02NHCNH-^/ 'N/ Q \ -S02NHCNH - ^ / 'N

N_^ZN_ ^ Z

10 X Z Smp. i °C10 X Z Mp. in ° C

Cl Cl CH3 CH3 130-140Cl Cl CH3 CH3 130-140

Cl Cl CH3 CH30 182-184Cl Cl CH3 CH30 182-184

Cl Cl CH30 CH30 192-193 F Cl CH3 CH3 171-175 15 F Cl CH3 CH30 190-191 F Cl CH-jO CH30 275Cl Cl CH30 CH30 192-193 F Cl CH3 CH3 171-175 F Cl CH3 CH30 190-191 F Cl CH-jO CH30 275

Cl CH3 CH3 CH3 188-189Cl CH3 CH3 CH3 188-189

Cl CH3 CH3 CH30 187Cl CH3 CH3 CH30 187

Cl CH3 CH30 CH30 148-151 20 CH30 Cl CH30 CH30 178Cl CH3 CH30 CH30 148-151 20 CH30 Cl CH30 CH30 178

Tabel IV-E 25 o N /x R5-/~θ\—SO-NHCNH- / \Table IV-E 25 o N / x R5- / ~ θ \ -SO-NHCNH- / \

MTMT

30 R30 R

R? R^ 'X Z Smp. i °CR? R 2 X Z Mp. in ° C

Cl Cl CH30 CH30 182-190 CH30 CH30 CH30 CH30 218-219 NO- Cl CH,0 CH- 163-164 35 1 j jCl Cl CH30 CH30 182-190 CH30 CH30 CH30 CH30 218-219 NO- Cl CH, 0 CH- 163-164 35 1 j j

Tabel IV-FTable IV-F

32 14934332 149343

OISLAND

r® O Xr® O X

\-- S N—^\ - S N— ^

5 / Q \-S02NHCNH-// xN5 / Q \ -S02NHCNH - // xN

V ^^2V ^^ 2

R^_ X Z Snip, i °CR ^ _ X Z Snip, i ° C

10 Cl Cl CH3 CH3 190-19210 Cl 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 CH3CH20 CH3 155-159

Cl Cl CH3CH20 CH30 147-149 15 CH3 CH3 CH3 CH30 160-163 CH3 CH3 CH30 CH30 169-173 CH-,0 Cl CH, CH-,0 174-179 3 3 3 CH30 Cl CH30 CH30 165 CH30 Cl CH3CH20 CH3 183-183,5 20 CH30 F CH30 CH30 201-203 F F CH3 CH3 164-165 F F CH30 CH30 206-208Cl Cl CH3CH20 CH30 147-149 15 CH3 CH3 CH3 CH30 160-163 CH3 CH3 CH30 CH30 169-173 CH-, 0 Cl CH, CH-, 0 174-179 3 3 3 CH30 Cl CH30 CH30 165 CH30 Cl CH3CH20 CH3 183- 183.5 20 CH30 F CH30 CH30 201-203 FF CH3 CH3 164-165 FF CH30 CH30 206-208

Cl CH30 CH3 CH30 176 ci ch3o ch3o ch3o 201 25 Cl CF3 CH3 CHsO 177-178Cl CH30 CH3 CH30 176 ci ch3o ch3o ch3o 201 Cl CF3 CH3 CHsO 177-178

Cl CF3 CH30 CH30 165-167Cl CF3 CH30 CH30 165-167

Cl H CH30 CH3 110-112 salt med CLjCOOCl H CH30 CH3 110-112 salt with CL 2 COO

Cl H CH30 CH3 olie (CH3CH2CH2CH2) 4N+ saltCl H CH30 CH3 oil (CH3CH2CH2CH2) 4N + salt

Cl H CH30 CH3 olie [CH3 (CH2) g] 4N+ salt 30 Cl N02 CH3 CH3 142-144Cl H CH30 CH3 oil [CH3 (CH2) g] 4N + salt Cl1 NO2 CH3 CH3

Cl N02 CH30 CH30 168-174 CH30 CH3 CHsO CH30 210-213 F CH3 CH3 CH3 180-182 F CH3 CH3 CH30 185-186 35 33 149343Cl N02 CH30 CH30 168-174 CH30 CH3 CHsO CH30 210-213 F CH3 CH3 CH3 180-182 F CH3 CH3 CH30 185-186 35 33 149343

OISLAND

R3 R6 X Z Smp. i °CR3 R6 X Z Mp. in ° C

F CH3 CH30 CH30 191-192 CH3 F CH3 CH3 201-205 CH3 F CH30 CH30 183-184 5 CELjS Cl CH3 CH30 95-100 CH3S Cl CH30 CH30 190-194 CH3 N02 CH3 CH30 190-191 CH3 N02 CH3 CH30 190-230 (sønderdeling) Na salt CH3 N02 CH30 CH30 142-145 10 CH3 (CH3)2CH CH3 CH3 167 CH3 (CH3)2CH CH3 CH30 115 CH3 (CH3)2CH CH30 CH30 135 CH3CH20 Cl CH3 CH30 179-181 CH3CH20 CH3CH20 CH3 CH3 134-136 15 CH,CH90 CH,CH90 CH.O CH30 187-188 CH3 Cl CH3 CH3 189-191F CH3 CH30 CH30 191-192 CH3 F CH3 CH3 201-205 CH3 F CH30 CH30 183-184 5 CELjS Cl CH3 CH30 95-100 CH3S Cl CH30 CH30 190-194 CH3 N02 CH3 CH30 190-191 CH3 N02 CH3 CH30 190-230 (decomposition) Na salt CH3 NO2 CH30 CH30 142-145 10 CH3 (CH3) 2CH CH3 CH3 167 CH3 (CH3) 2CH CH3 CH30 115 CH3 (CH3) 2CH CH30 CH30 135 CH3CH20 Cl CH3 CH30 179-181 CH3CH20 CH3CH20 CH3 CH3 134- 136 CH, CH90 CH, CH90 CH.O CH30 187-188 CH3 Cl CH3 CH3 189-191

Br Br CH3 CH3 204-205Br Br CH3 CH3 204-205

Br Br CH3 CH30 178-180Br Br CH3 CH30 178-180

Br Br CH3° CH3° over 275 20 CH30 CH30 CH3 CH3 144-150 CHgO CH30 CH3 CH30 187-205 (sønderdeling) CH30 CH30 CH30 CH30 olie (CH3CH2CH2CH2) 4N+ salt CH30 CH30 CH30 CH30 187-188 CH30 CH30 CH3CH20 CH3 96-100 25 CH30 CH30 CH3CH20 CH30 138-141 (CH3)2CH (CH3)2CH CH30 CH30 123-128 CH,CHo0 Cl CH O CH^O 174-178 3 2 3 -J 1 35Br Br CH3 ° CH3 ° over 275 20 CH30 CH30 CH3 CH3 144-150 CHgO CH30 CH3 CH30 187-205 (decomposition) CH30 CH30 CH30 CH30 oil (CH3CH2CH2CH2) 4N + salt CH30 CH30 CH30 CH30 187-188 CH30 CH30 CH3CH20 CH3 96-100 CH30 CH30 CH3CH20 CH30 138-141 (CH3) 2CH (CH3) 2CH CH30 CH30 123-128 CH, CHOO Cl CH O CH ^ O 174-178 3 2 3 -J 1 35

OISLAND

Tabel IV-GTable IV-G

34 14934334 149343

/R? O X/ R? O X

5 /n \“SO-NHCNH- VH7 3 2 N=<5 / n \ "SO-NHCNH-VH7 3 2 N = <

XR XZXR XZ

r7 X Z Smp. i °Cr7 X Z Mp. in ° C

1010

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 171-172 15 Cl CH3 CH30 CH30 173-176 F F CH3 CH3 192-193 F F CH3 CH30 213-215 F F CH30 CH30 275 20Cl CH3 CH3 CH30 171-172 15 Cl CH3 CH30 CH30 173-176 F F CH3 CH3 192-193 F F CH3 CH30 213-215 F F CH30 CH30 275 20

Tabel IV-HTable IV-H

*1 _ O N_/X* 1 _ O N_ / X

R4 R6 X Z Smp. i °CR4 R6 X Z Mp. in ° C

30 Cl Cl CH3 CH3 210-21330 Cl Cl CH3 CH3 210-213

Cl Cl CH30 CH30 207 35 35Cl Cl CH30 CH30 207 35 35

OISLAND

U93Å3U93Å3

Tabel IV-I O M ^ 5 r5- /q ^-so2nhcnh-^=1iTable IV-I O M ^ 5 r5- / q ^ -so2nhcnh - ^ = 1i

10 R^ X Z Smp. i °C10 R 2 X Z Mp. in ° C

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 182-185 15Cl Cl CH30 CH30 280 NO2 CH30 CH3 CH30 182-185 15

Tabel IV-J 0 N_^XTable IV-J 0 N_ ^ X

20 R5— /"o \ -SO-NHCNH- / NR 5 - / - O -SO-NHCNH- / N

4ΛΗ 3 N-<Z4ΛΗ 3 N- <Z

R RR R

3 4 5 o3 4 5 o

R R R X Z Smp. i CR R R X Z Mp. i C

2525

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 1 35Cl Cl Cl CH30 CH30 175-178 1 35

Tabel IV-KTable IV-K

36 o 14934336 o 149343

R\_ 0 N_</XR \ _ 0 N _ </ X

/^-SO^HCHH-^ N/ ^ - SO ^ HCHH- ^ N

\ \ 3 Z\ \ 3 Z

R RR R

R3 R4 R6 X Z Smp. i °CR3 R4 R6 X Z Mp. in ° C

10 CH3 CH3 N02 CH3 CH30 182-184 (sønderdeling) CH3 CH3 N02 CH3 CH3 196-197 (sønderdeling)CH3 CH3 NO2 CH3 CH30 182-184 (decomposition) CH3 CH3 NO2 CH3 CH3 196-197 (decomposition)

Tabel IV-L 15Table IV-L 15

R7 _ XR7 _ X

i-*' ° /qX-so^hcnh-,' ni- * '° / qX-so ^ hcnh-, a

a' \ 3 R4 Ra '\ 3 R4 R

2020

R^ R^ R^ X Z Smp. i °CR ^ R ^ R ^ X Z Mp. in ° C

CH3 Cl Cl CH3 CH3 168-170 CH3 Cl Cl CH30 CH3 176-178 CH30 Cl Cl ch3° CH30 173-175 25CH3 Cl Cl CH3 CH3 168-170 CH3 Cl Cl CH30 CH3 176-178 CH30 Cl Cl ch3 ° CH30 173-175 25

Tabel IV-MTable IV-M

r6 O /Xr6 O / X

v „ N / R5- ^ Qy -SQ2NHCNH-^^N 30 ' \r3 -^zv "N / R5- ^ Qy -SQ2NHCNH - ^^ N 30 '\ r3 - ^ z

R^ R^ R^ X Z Smp. i °CR ^ R ^ R ^ X Z Mp. in ° C

Cl Cl Cl CH3 CH3 184-186Cl Cl Cl CH3 CH3 184-186

Cl Cl Cl CH3 CH30 169-171 35 Cl Cl Cl CH30 CH30 165-168 CH30 Cl CH30 CH30 CH30 195Cl Cl Cl CH3 CH30 169-171 35 Cl Cl Cl CH30 CH30 165-168 CH30 Cl CH30 CH30 CH30 195

OISLAND

37 14934337 149343

Tabel IV-N 7Table IV-N 7

R O XR O X

R5-/ø^-S02NHCNH-R5 / island ^ -S02NHCNH-

5 ' ''R3 ^Z5 '' 'R3 ^ Z

R^ R^ R^ X Z Smp. 1 °CR ^ R ^ R ^ X Z Mp. + 1 ° C

CH3 CH3 CH3 CH3 CH3 205-207 CH3 CH3 CH3 CH3 CH30 177-186 10 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 10 CH3 CH3 CH3 CH30 CH30 160-167 F F F CH3 CH3 163-169 F F CH CH3 CH30 152-155 F F CH30 CH30 194-196

Cl Cl Cl CH3 CH3 188-190 15 Cl Cl Cl CH3 CH30 159-161Cl Cl Cl CH3 CH3 188-190 15 Cl Cl Cl CH3 CH30 159-161

Cl Cl Cl CH30 CH30 166-168Cl Cl Cl CH30 CH30 166-168

Tabel IV-0Table IV-0

20 r6\ R? O20 r6 \ R? ISLAND

>OJ-S02NHCNH-^ R4 R3> OJ-SO2NHCNH- ^ R4 R3

25 R^ R^ X Z Smp. i °C25 R ^ R ^ X Z Mp. in ° C

CH3 CH3 CH3 CH3 CH3 CH3 200-205 CH3 CH3 CH3 CH3 CH3 CH30 195-197 CH3 CH3 CH3 CH3 CH30 CH30 185-189CH3 CH3 CH3 CH3 CH3 CH3 200-205 CH3 CH3 CH3 CH3 CH3 CH30 195-197 CH3 CH3 CH3 CH3 CH30 CH30 185-189

Cl Cl Cl Cl CH3 CH30 187 30 Cl Cl Cl Cl CH30 CH30 250Cl Cl Cl Cl CH3 CH30 187 30 Cl Cl Cl Cl CH30 CH30 250

Eksempel 12 N-[(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)aminocarbonyl]- -2-thiophensulfonamid_ 35 Til en suspension af 14,0 g 2-amino-4-methoxy-6-me- thyl-1,3,5-triazin i 300 ml acetonitril sættes dråbevis 19 g o 38 149343 thiophen-2-sulfonylisocyanat. Efter omrøring i 6 timer filtreres blandingen, hvorved fås det ønskede faste stof med smp. 182-184°C.Example 12 N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-thiophenesulfonamide To a suspension of 14.0 g of 2-amino-4-methoxyphenyl 6-Methyl-1,3,5-triazine in 300 ml of acetonitrile is added dropwise to thiophene-2-sulfonylisocyanate. After stirring for 6 hours, the mixture is filtered to give the desired solid, m.p. 182-184 ° C.

Analogt med den i eksempel 12 beskrevne fremgangs-5 måde og under anvendelse af ækvivalente mængder af det passende amino-1,3,5-triazinderivat og sulfonylisocyanat kan de nedenfor i tabel V anførte forbindelser fremstilles.By analogy to the procedure described in Example 12 and using equivalent amounts of the appropriate amino-1,3,5-triazine derivative and sulfonyl isocyanate, the compounds listed below in Table V can be prepared.

Tabel V-ATable V-A

10 0 II N· M··^10 0 II N · M ·· ^

,-.-SO-NH-C-NH- / SN, -.- SO-NH-C-NH- / SN

XX HXX H

R9 V°R9 V °

_R9 R^ X Z Smp. i °C_ R9 R ^ X Z Mp. in ° C

Cl Cl CH3 CH3 127-133 20 Cl Cl CH3 CH30 165-171Cl Cl CH3 CH3 127-133 20 Cl Cl CH3 CH30 165-171

Cl Cl CH30 CH30 181-184Cl Cl CH30 CH30 181-184

Tabel V-B 25Table V-B 25

_ O X_ O X

fj H „ N /fj H „N /

L ]^S00NHCNH- (/ VNL] S00NHCNH- (/ VN

2 V=/ R8 2 30 82 V = / R8 2 30 8

R X Z Q Smp. i °CR X Z Q Mp. in ° C

H CH3 CH3 S 174-176 H CH3 CH30 S 182-184 H CH30 CH30 S 191-192 35 Cl CH3 CH3 S 192-195H CH3 CH3 S 174-176 H CH3 CH30 S 182-184 H CH30 CH30 S 191-192 35 Cl CH3 CH3 S 192-195

Cl CH30 CH30 S 193-195 H CH3CH2 CH3 S 132-138 H CH3S CH3 S 223-225Cl CH30 CH30 S 193-195 H CH3CH2 CH3 S 132-138 H CH3S CH3 S 223-225

OISLAND

39 14934339 149343

Eksempel 13 N-[(4,6-Dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]-1- -naphthalensulfonamid_Example 13 N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -1- -naphthalenesulfonamide

Til en suspension af 16 g 2-amino-4,6-dimethoxy-l,3,5-5 -triazin i 400 ml acetonitril sættes dråbevis under omrøring 23,3 g 1-naphthalensulfonylisocyanat. Blandingen omrøres i 14 timer, og det dannede faste produkt frafiltreres. Efter vaskning med ethylether har produktet smp. 171-172°C.To a suspension of 16 g of 2-amino-4,6-dimethoxy-1,3,5-5-triazine in 400 ml of acetonitrile is added dropwise with stirring 23.3 g of 1-naphthalenesulfonylisocyanate. The mixture is stirred for 14 hours and the resulting solid product is filtered off. After washing with ethyl ether, the product has m.p. 171-172 ° C.

Analogt med den i eksempel 13 beskrevne fremgangsmåde 10 og under anvendelse af ækvivalente mængder af det passende amino-l,3,5-triazin og sulfonylisocyanat, kan de nedenfor i tabel VI anførte forbindelser fremstilles.Analogous to the procedure 10 described in Example 13 and using equivalent amounts of the appropriate amino-1,3,5-triazine and sulfonyl isocyanate, the compounds listed in Table VI can be prepared below.

Tabel VI 15Table VI 15

SO-NHCNH-A YSO-NHCNH-A Y

yv I Wyv I W

ΑΛ z 2020 z 20

X Z Smp. i °CX Z Mp. in ° C

CH3 CH3 179-183 CH3 CH30 186-188 25 CH30 CH30 171-172CH3 CH3 179-183 CH3 CH30 186-188 25 CH30 CH30 171-172

Eksempel 14 N-[(4,6-Dimethoxy-l,3,5-triazin-2-yl)aminothioxomethyl]- -benzensulfonamid______ 30 En blanding af 20 g benzensulfonylisothiocyanat, 15,6 g 2-amino-4,6-dimethoxy-l,3,5-triazin, 250 ml acetonitril og en katalytisk mængde dibutyltindilaurat omrøres i 24 timer. Efter filtrering til fjernelse af uomsat triazin fordampes acetonitrilet, hvorved fås en gummiagtig remanens.Example 14 N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) aminothioxomethyl] -benzenesulfonamide A mixture of 20 g of benzenesulfonylisothiocyanate, 15.6 g of 2-amino-4,6-dimethoxy -1, 3,5-triazine, 250 ml of acetonitrile and a catalytic amount of dibutyltin dilaurate are stirred for 24 hours. After filtration to remove unreacted triazine, the acetonitrile is evaporated to give a gummy residue.

35 Ved triturering af dette materiale med ethylether sker der udfældning af det ønskede produkt, som isoleres ved filtrering, smp. 148-150°C.35 Trituration of this material with ethyl ether precipitates the desired product, which is isolated by filtration, m.p. 148-150 ° C.

40 0 14934340 0 149343

Analogt med den i eksempel 14 beskrevne fremgangsmåde med en ækvivalent mængde af det passende sulfonyl-isothiocyanat og aminotriazin, kan de nedenfor i tabel VII anførte forbindelser fremstilles.By analogy to the procedure described in Example 14 with an equivalent amount of the appropriate sulfonyl isothiocyanate and aminotriazine, the compounds listed below in Table VII can be prepared.

55

Tabel VII STable VII S

r1so2nhcnhr2 10r1so2nhcnhr2 10

R~*~ R2 Smp. i °CR ~ * ~ R2 m.p. in ° C

y- N-^°CH3 // λ- -(/ y 182-185y- N- ^ ° CH3 // λ- - {/ y 182-185

Nil ^OCH,NIL ^ AND,

15 J15 J

/CH3/ CH 3

Qn—S JQn-S J

-ζΤΪ 142-144-ζΤΪ 142-144

CH3 ^CHCH3 ^ CH

20 s CH3? 0°η3 (? -(/ % 188-190 \—/ n.=/ (Sønderdeling) OCH, 0CH320 s CH3? 0 ° η3 (? - (/% 188-190 \ - / n. = / (Decomposition)) AND, 0CH3

25 J25 J

Anvendelige præparater indeholdende forbindelserne med formlen I kan fremstilles på konventionel måde. Disse præparater indbefatter puddere, granulater, pellets, opløsninger, suspensioner, emulsioner, fugtepulvere, emulgerbare 30 koncentrater og lignende. Mange af disse kan anvendes direkte. Sprøjtepræparater kan strækkes i passende medier og anvendes i sprøjterumfang på fra nogle få liter til flere hundrede liter pr. hektar. Højkoneentrerede præparater anvendes primært som intermediære præparater til yderligere 35 o 4i 149343 formulering. Præparaterne indeholder stort set ca. 0,1--99 vægtprocent aktiv bestanddel og mindst en bestanddel valgt blandt (a) ca. 0,1 til 20% overfladeaktivt stof og (b) ca. 1-99,9% fast eller flydende fortyndingsmiddel.Useful compositions containing the compounds of formula I can be prepared in a conventional manner. These compositions include powders, granules, pellets, solutions, suspensions, emulsions, moisturizers, emulsifiable concentrates and the like. Many of these can be used directly. Spray preparations can be stretched in appropriate media and used in spray volumes of a few liters to several hundred liters per liter. acres. Highly concentrated preparations are primarily used as intermediates for further formulation. The preparations contain substantially approx. 0.1 to 99% by weight of active ingredient and at least one ingredient selected from (a) ca. 0.1 to 20% surfactant and (b) approx. 1-99.9% solid or liquid diluent.

5 Sædvanligvis indeholder præparaterne disse bestanddele i de i de følgende anførte omtrentlige mængders 10 15 20 25 30 35 42 149343 •μ > Η •μUsually the compositions contain these ingredients in the approximate amounts listed in the following 10 10 20 20 30 30 42 42 149343 • μ> Η • μ

XX

ta <ΰta <ΰ

DD

Π3 !_j ^ ι++ <D ο mo m μ Ό Η η cm m η cm <u rø i i i i t iΠ3! _J ^ ι ++ <D ο mo m µ Ό Η η cm m η cm <u ro i i i i i t i

>·Η ι-H OHOO O> · Η ι-H OHOO O

0 g •cn S' -Η σι 1,3 “ _ G η in σι σι ο >4(1) i" m to m οι i-i0 g • cn S '-Η σι 1.3 "_ G η in σι σι ο> 4 (1) i" m to m οι i-i

+1¾ I I I I I I+ 1¾ I I I I I I I

μ rø o oooin o 0 ·Η ^ *3< Γ-~ 1¾ g «—I 0) 'ϋ w Ό h Go ο o in m σι η >ιοσι in m cm σι σιμ rø o oooin o 0 · Η ^ * 3 <Γ- ~ 1¾ g «—I 0) 'ϋ w Ό h Go ο o in m σι η> ιοσι in m cm σι σι

> ·Η -μ I I I I I I> · Η -µ I I I I I I

+>w o moHH o H X CD · CM H - σι α) < Λ Ο Λ (0 Eh+> w o moHH o H X CD · CM H - σι α) <Λ Ο Λ (0 Eh

rH CDrH CD

g μ « i g ta μ -μ « cD μ Λ CD <D μ φ μ G η cu * CP CD Ο Η μ G D> -η cd α) (ϋ -Η Η ω Ρι Όg μ «i g ta μ -μ« cD μ Λ CD <D μ φ μ G η cu * CP CD Ο Η μ G D> -η cd α) (ϋ -Η Η ω Ρι Ό

G G G £ <DG G G £ <D

0 w g ^ CD CP μ0 w g ^ CD CP µ

CD -rl ^ CD μ Di O <DCD -rl ^ CD μ Di O <D

μ w h cd ω μ cd cftcD-μ s μ-μµ w h cd ω µ cd cftcD-µ s µ-µ

> CD 0 > G CO CD G> CD 0> G CO CD G

ι-H Dl Ή μ 4-> CDι-H Dl Ή μ 4-> CD

D « mod 11 ID id O h Οι g μ g g di μ η g cd CD MCDHCD-H CD G 0 +> 4J ID GDC Ο Φ Ό CM (0 di-hogg so ιβ ή μ GH-H-Ho g g μ ’θ. gD «mod 11 ID id O h Οι g μ gg di μ η g cd CD MCDHCD-H CD G 0 +> 4J ID GDC Ο Φ Ό CM (0 di-hogg so ιβ ή μ GH-H-Ho gg μ ' θ. g

Pi O CD — X > 111 CD 55 OiPi O CD - X> 111 CD 55 Oi

OISLAND

43 14934343 149343

Der kan naturligvis anvendes lavere eller højere koncentration af aktiv bestanddel afhængig af den tilsigtede anvendelse og forbindelsens fysiske egenskaber. Det er sommetider ønskeligt med større mængder overfladeaktivt stof 5 i forhold til aktiv bestanddel, og dette opnås ved inkorporering i præparatet eller ved tankblanding.Of course, lower or higher concentration of active ingredient may be used depending on the intended use and the physical properties of the compound. It is sometimes desirable with greater amounts of surfactant 5 relative to active ingredient, and this is achieved by incorporation into the composition or by tank mixing.

Typiske faste fortyndingsmidler er beskrevet i Watkins et al., "Handbook of Insecticide Dust Diluents and Carriers", 2. udgave, Dorland Books, Caldwell, New Jersey.Typical solid diluents are described in Watkins et al., "Handbook of Insecticide Dust Diluents and Carriers," 2nd Edition, Dorland Books, Caldwell, New Jersey.

10 De mere absorptive fortyndingsmidler foretrækkes til fugte- pulvere, og de tungere til puddere. Typiske flydende fortyndingsmidler og opløsningsmidler er beskrevet i Mardsden, "Solvents Guide", 2. udgave^ Intersicience, New York, 1950. Opløselighed under 0,1% foretrækkes til suspensionskoncen-15 trater, og opløsningskoncentrater er fortrinsvis stabile mod faseseparation ved 0°C. En oversigt over overfladeaktive midler og anbefalede anvendelser er anført i "McCutcheon's Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood, New Jersey, samt i Sisely og Wood, "Encyclopedia of 20 Surface Active Agents", Chemical Publ. Co., Inc. New York, 1964. Alle præparater kan indeholde mindre mængder additiver med henblik på at reducere skum, kagedannelse, korrosion, mikrobiologisk vækst og lignende.10 The more absorbent diluents are preferred for moisturizers and heavier for powders. Typical liquid diluents and solvents are described in Mardsden, "Solvent's Guide," 2nd Edition ^ Intersicience, New York, 1950. Solubility below 0.1% is preferred for suspension concentrates and solvent concentrates are preferably stable against phase separation at 0 ° C. . An overview of surfactants and recommended uses is given in "McCutcheon's Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood, New Jersey, and in Sisely and Wood, "Encyclopedia of 20 Surface Active Agents," Chemical Publ. Co., Inc. New York, 1964. All compositions may contain minor amounts of additives to reduce foam, cake formation, corrosion, microbiological growth, and the like.

Metoderne til fremstilling af sådanne præparater er 25 velkendt. Opløsninger fremstilles ved simpel blanding af bestanddelene. Findelte faste præparater fremstilles ved blanding og sædvanligvis formaling i en hammermølle eller væskeenergimølle. Suspensioner fremstilles ved vådformaling, jfr. f.eks. den i beskrivelsen til USA-patent nr. 3.060.084 30 beskrevne fremgangsmåde. Granulater og pellets kan fremstilles ved sprøjtning af det aktive materiale på præformede granulatbærere eller ved agglomerering. Jfr. J.E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, side 147ff, og "Perry's Chemical Engineer's Handbook", 4. udgave, 35 McGraw-Hill, New York, 1963, side 8-59ff.The methods of preparing such compositions are well known. Solutions are prepared by simple mixing of the ingredients. Finely divided solid compositions are prepared by mixing and usually milling in a hammer mill or liquid energy mill. Suspensions are prepared by wet milling, cf. eg. the process described in U.S. Patent No. 3,060,084. Granules and pellets can be prepared by spraying the active material onto preformed granular carriers or by agglomeration. Cf.. JE Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, page 147ff, and "Perry's Chemical Engineer's Handbook," 4th Edition, 35 McGraw-Hill, New York, 1963, pages 8-59ff.

149343 44 i i > o i149343 44 i i> o i

For yderligere information vedrørende teknikken i forbindelse med fremstilling af præparater kan eksempelvis hen- ‘ vises til beskrivelsen til USA-patent nr. 3.235.361, spalte j 6, linie 16 til spalte 7 linie 19 og eksempel 10-41, beskri- i 5 velsen til USA-patent nr. 3.309.192 spalte 5, linie 43 til · spalte 7 linie 62 og eksemplerne 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 og 169-182, beskrivelsen i±il USA-patent nr. 2.891.855, spalte 3, linie 66 til spalte 5, linie 17 og eksempel 1-4, G.C. Klingman, "Weed 10 Control as a Science", John Wiley & Sons, Inc., New York, 1961, side 81-96 samt J.D. Fryer and S.A. Evans, "Weed Control Handbook", 5. udgave, Blackwell Scientific Publications, Oxford, 1968, side 101-103.For further information on the technique of preparation of compositions, reference may be made, for example, to U.S. Patent No. 3,235,361, column 6, line 16 to column 7, line 19, and examples 10-41, described in U.S. Pat. U.S. Patent No. 3,309,192, 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, disclosed in ± 1 to U.S. Patent No. 2,891,855, column 3, line 66 to column 5, line 17, and Examples 1-4, GC Klingman, "Weed 10 Control as a Science," John Wiley & Sons, Inc., New York, 1961, pages 81-96 and J.D. Fryer and S.A. Evans, "Weed Control Handbook", 5th Edition, Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

I de følgende eksempler er alle dele på vægtbasis, 15 med mindre andet er anført.In the following examples, all parts are by weight, unless otherwise stated.

Eksempel 15 Fugtepulver N-[(4,6-dimethylpyrimidin-2-yl)aminO-2Q carbonyl]benzensulfonamid 80%Example 15 Moisturizing Powder N - [(4,6-Dimethylpyrimidin-2-yl) aminoO-2Q carbonyl] benzenesulfonamide 80%

Natriumalkylnaphthalensulfonat 2%Sodium alkyl naphthalenesulfonate 2%

Natriumligninsulfonat 2%Sodium lignin sulfonate 2%

Syntetisk amorft siliciumdioxid 3%Synthetic amorphous silica 3%

Kaolinit 13% 25 Bestanddelene blandes, formales i en hammermølle, ind til alle faste stoffer i alt væsentlig har en størrelse på under 50 pm, hvorefter der genblandes.Kaolinite 13% 25 Ingredients are mixed, ground in a hammer mill, until all solids are substantially less than 50 microns in size and then re-mixed.

Eksempel 16 fugtepulver 3Q N-[(4-methoxy-6-methylpyrimidin-2-yl)- aminocarbonyl]-2-chlor-5-methoxy-benzensulfonamid 50%Example 16 Moisturizing Powder 3Q N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide 50%

Natriumalkylnaphthalensulfonat 2%Sodium alkyl naphthalenesulfonate 2%

Lavviskos methylcellulose 2%Low viscous methyl cellulose 2%

Diatoméjord 46% 35 Bestanddelene blandes, formales groft i en hammermølle og formales derpå i en luftmølle til dannelse af partiklerDiatomaceous earth 46% 35 The ingredients are mixed, coarsely ground in a hammer mill and then ground in an air mill to form particles

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45 149363 af aktivt stof med en diameter på i alt væsentligt mindre end 10 pm. Produktet genblandes inden emballering.45 149363 of active substance having a diameter of substantially less than 10 µm. The product is remixed before packaging.

5 Eksempel 17Example 17

Granulatgranules

Pugtepulver ifølge eksempel 16 5%Powder Powder of Example 16 5%

Attapulgitgranulat (0,84-0,42 mm) 95%Attapulgite granules (0.84-0.42 mm) 95%

En opslæmning af fugtepulveret indeholdende omtrent-10 lig 25% fast stof sprøjtes på overfladen af attapulgitgra- nulatet i et dobbeltkegleblandeapparatur. Granulatet tørres og emballeres.A slurry of the moisture powder containing about 10% solids is sprayed onto the surface of the attapulgite granule in a double cone mixer. The granulate is dried and packaged.

Eksempel 18 15 Ekstruderede pellets N-[(4-methoxy-6-methylpyrimidin-2-yl)-aminocarbonyl]-2-chlorbenzensulfon-amid 25%Example 18 Extruded Pellets N - [(4-Methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide 25%

Vandfri natriumsulfat 10% Råt calciumligninsulfonat 5% 20Anhydrous sodium sulfate 10% Crude calcium lignin sulfonate 5% 20

Natriumalkylnaphthalensulfonat 1%Sodium alkyl naphthalenesulfonate 1%

Calcium/magnesiumbentonit 59%Calcium / magnesium bentonite 59%

Bestanddelene blandes, formales i en hammermølle og fugtes med ca. 12% vand. Blandingen ekstruderes som cylindre 25 med en diameter pa ca. 3 mm, som afskæres til dannelse af pellets med en længde på ca. 3 mm. Disse kan anvendes direkte efter tørring, eller de tørrede pellets kan knuses således, at materialet passerer en sigte med maskevidde på 0,84 mm. Granulatet, som tilbageholdes på en sigte med en 30 maskeåbning på 0,42 mm, kan emballeres til anvendelse, og de finere partikler recirkuleres.The ingredients are mixed, ground in a hammer mill and moistened with approx. 12% water. The mixture is extruded as cylinders 25 having a diameter of approx. 3 mm which is cut to form pellets with a length of approx. 3 mm. These can be used directly after drying or the dried pellets can be crushed so that the material passes a sieve with a mesh width of 0.84 mm. The granules which are retained on a sieve with a mesh opening of 0.42 mm can be packaged for use and the finer particles recycled.

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Eksempel 19 Oliesuspension N- [ (4,6-dimethoxypyrimidin-2-yl)-amino- carbonyl]-2,5-dichlorbenzensulfonamid 25% g Polyoxyethylensorbitolhexaoleat 5% Højaliphatisk carbonhydridolie 70%Example 19 Oil suspension N- [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide 25% g Polyoxyethylene sorbitol hexaoleate 5% High aliphatic hydrocarbon oil 70%

Bestanddelene formales i en sandmølle, indtil de faste partikler har .en størrelse på mindre end ca. 5 jam. Den fremkomne suspension kan anvendes direkte, dog fortrinsvis efter 10 strækning med olier eller emulgering i vand.The ingredients are ground in a sand grinder until the solid particles have a size of less than approx. 5 jam. The resulting suspension can be used directly, but preferably after 10 stretching with oils or emulsifying in water.

Eksempel 20 Fugtepulver N-[(4,6-dimethylpyrimidin-2-yl)-amino-15 carbonyl]-2,6-dichlorbenzensulfonamid 20% .Example 20 Moisturizing Powder N - [(4,6-Dimethylpyrimidin-2-yl) -amino-carbonyl] -2,6-dichlorobenzenesulfonamide 20%.

Natriumalkylnaphthalensulfonat 4%Sodium alkyl naphthalenesulfonate 4%

Natriumligninsulfonat 4%Sodium lignin sulfonate 4%

Lavviskos methylcellulose 3%Low viscous methyl cellulose 3%

Attapulgit 69% 20Attapulgit 69% 20

Bestanddelene blandes omhyggeligt. Efter formaling i en hammermølle til dannelse af partikler, der i alt væsentligt er mindre end 100 jam, genblandes materialet og sigtes gennem en sigte med maskevidde på 0,3 mm, hvorefter produktet 25 emballeres.The ingredients are mixed thoroughly. After milling in a hammer mill to form particles substantially less than 100 µm, the material is re-mixed and sieved through a 0.3 mm mesh screen, after which the product is packaged.

Eksempel 21Example 21

Granulat med lav styrke N-t(4-methoxy-6-methylpyrimidin-2-yl)-amino-30 carbonyl] -2-methylbenzensulfonamid 1% N,N-dimethylformamid 9%Low-strength granular N-t (4-methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2-methylbenzenesulfonamide 1% N, N-dimethylformamide 9%

Attapulgitgranulat (0,84-0,42 mm) 90%Attapulgite granules (0.84-0.42 mm) 90%

De aktive bestanddele opløses i opløsningsmidlet, og 35 opløsningen sprøjtes på støvfrit granulat i et dobbeltkegle- blandeapparatur. Efter at sprøjtning af opløsningen er af- 47 149343 o sluttet, startes hlandeapparaturet i et kort tidsrum, hvorefter granulatet emballeres.The active ingredients are dissolved in the solvent and the solution is sprayed onto dust-free granules in a double-cone mixer. After spraying of the solution is completed, the mixing apparatus is started for a short period of time, after which the granulate is packaged.

Eksempel 22 5 Vandig suspension N- [ (4,6-dimethylpyrimidin-2-yl)-aminocar- bonyl]-benzensulfonamid 40%Example 22 Aqueous suspension of N- [(4,6-dimethylpyrimidin-2-yl) -aminocarbonyl] -benzenesulfonamide 40%

Polyacrylsyrefortykkelsesmiddel 0,3%Polyacrylic Acid Thickener 0.3%

Dodecylphenolpolyethylenglycolether 0,5% 10 Dinatriumphosphat 1%Dodecylphenol polyethylene glycol ether 0.5% Disodium phosphate 1%

Mononatriumphosphat 0,5%0.5% monosodium phosphate

Polyvinylalkohol 1,0%Polyvinyl alcohol 1.0%

Vand 56,7% 15 Bestanddelene blandes og formales i en sandmølle til dannelse af partikler, der i alt væsentligt er mindre end 5 )im.Water 56.7% 15 The ingredients are mixed and ground in a sand mill to form particles which are substantially less than 5 µm.

Eksempel 23 20 Opløsning N-[(4-methoxy-6-methylpyrimidin-2-yl)-amino-carbonyl] -2-chlorbenzensulfonamid--natriumsalt 5%Example 23 Solution N - [(4-methoxy-6-methylpyrimidin-2-yl) amino carbonyl] -2-chlorobenzenesulfonamide - sodium salt 5%

Vand · 95%Water · 95%

Saltet sættes direkte til vandet under omrøring til 25 dannelse af opløsningen, som derpå kan emballeres med henblik på anvendelse.The salt is added directly to the water with stirring to form the solution which can then be packaged for use.

Eksempel 24Example 24

Granulat med lav styrke 30 -- N-t(4,6-dimethylpyrimidin-2-yl)-aminocar- bonyl]-2,6-dichlorbenzensulfonamid 0,1%Low Strength Granules 30 - N-t (4,6-Dimethylpyrimidin-2-yl) -aminocarbonyl] -2,6-dichlorobenzenesulfonamide 0.1%

Attapulgitgranulat (0,84-0,42 mm) 99,9%Attapulgite granules (0.84-0.42 mm) 99.9%

Den aktive bestanddel opløses i et opløsningsmiddel, og opløsningen sprøjtes på det støvfri granulat i et dobbelt- 35 kegleblandeapparatur. Efter at sprøjtning af opløsningen er 0 .The active ingredient is dissolved in a solvent and the solution is sprayed onto the dust-free granule in a double cone mixer. After spraying the solution is 0.

48 149343 afsluttet, opvarmes materialet til fordampning af opløsningsmidlet. Materialet henstilles til afkøling, hvorefter det emballeres.48 149343, the solvent is heated to evaporate the solvent. The material is left to cool and then packaged.

5 Eksempel 25Example 25

Granulat N-[(4,6-dimethoxypyrimidin-2-yl)-aminocar- bonyl]-2,5-dichlorbenzensulfonamid 80%Granulate N - [(4,6-dimethoxypyrimidin-2-yl) -aminocarbonyl] -2,5-dichlorobenzenesulfonamide 80%

Fugtemiddel 1% 10 Rå ligninsulfonatsalt (indeholdende 5-20% af de naturlige sukkerarter) 10%Wetting agent 1% 10 Raw lignin sulfonate salt (containing 5-20% of the natural sugars) 10%

Attapulgitler 9%Attapulgitler 9%

Bestanddelene blandes og formales således, at de passerer en 100 mesh-sigte. Dette materiale sættes derpå til 15 et fluid bed granuleringspparat, hvor luftstrømmen indstil les til forsigtig fluidisering af materialet, og en fin tåge af vand sprøjtes på det fluidiserede materiale. Fluidiseringen og sprøjtningen fortsættes, indtil granulatet med den ønskede størrelse er dannet. Sprøjtningen afbrydes, men fluidiseringen 20 opretholdes, eventuelt under varmetilførsel, indtil vandind holdet er formindsket til det ønskede niveau, sædvanligvis under 1%. Derefter udtages materialet, sigtes til det ønskede størrelsesområde, sædvanligvis 1410-149 pm, og emballeres med henblik på anvendelse.The ingredients are mixed and ground to pass a 100 mesh screen. This material is then added to a fluid bed granulator where the air flow is adjusted to gently fluidize the material and a fine mist of water is sprayed onto the fluidized material. The fluidization and spraying is continued until the granulate of the desired size is formed. Spraying is interrupted, but fluidization 20 is maintained, optionally during heat application, until the water content is reduced to the desired level, usually below 1%. Then, the material is taken out, sieved to the desired size range, usually 1410-149 µm, and packaged for use.

2525

Eksempel 26 Højkoneentreret præparat N-[(4,6-dimethylpyrimidin-2-yl)-amino- carbonyl]—2-thiophensulfonamid 99% 30 Silicaaerogel 0,5%Example 26 High Concentrated Preparation N - [(4,6-Dimethylpyrimidin-2-yl) -aminocarbonyl] -2-thiophenesulfonamide 99% Silica aerogel 0.5%

Syntetisk amorft siliciumdioxid 0,5%Synthetic amorphous silica 0.5%

Bestanddelene blandes og formales i en hammermølle til dannelse af et materiale, der stort set passerer en sigte med en sigteåbning på 0,3 mm. Koncentratet kan formuleres yderes ligere om nødvendigt.The components are blended and ground in a hammer mill to form a material which substantially passes a sieve with a sieve opening of 0.3 mm. The concentrate can be formulated more evenly if necessary.

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Eksempel 27 Fugtepulver N-t(4-methoxy-6-methylpyrimidin-2-yl)-amino -carbonyl]-2-chlorbenzensulfonamid 95% g Dioctylnatriumsulfosuccinat 0,1%Example 27 Moist powder N-t (4-methoxy-6-methylpyrimidin-2-yl) -amino-carbonyl] -2-chlorobenzenesulfonamide 95% g Dioctyl sodium sulfosuccinate 0.1%

Syntetisk finpulveriseret siliciumdioxid 4,9%Synthetic fine powder silica 4.9%

Bestanddelene blandes og formales på en hammermølle til dannelse af partikler, som i alt væsentligt er mindre end 100 ^im. Materialet sigtes gennem en US-sigte nr. 50, 10 hvorefter det emballeres.The ingredients are mixed and ground on a hammer mill to form particles substantially less than 100 µm. The material is sieved through a US sieve 50, 10 and then packaged.

Eksempel 28 Fugtepulver N-[(4-dimethoxypyrimidin-2-yl)-aminocarbonyl]--2,5-dichlorbenzensulfonamid 40% 15Example 28 Moisturizing Powder N - [(4-Dimethoxypyrimidin-2-yl) -aminocarbonyl] -2,5-dichlorobenzenesulfonamide 40%

Natriumligninsulfonat 20%Sodium lignin sulfonate 20%

Montmorillonitler 40%Montmorillonitler 40%

Bestanddelene blandes omhyggeligt, formales groft i en hammermølle og derpå i en luftmølle til dannelse af partikler, der i alt væsentligt er mindre end 10 um. Materialet 20 genblandes og emballeres derpå.The ingredients are thoroughly mixed, ground coarsely in a hammer mill and then in an air mill to form particles substantially less than 10 µm. The material 20 is then re-mixed and packaged.

Eksempel 29 Oliesuspension N-[(4-methoxy-6-methylpyrimidin-2-yl)-amino-25 carbonyl]-2-methylbenzensulfonamid 35%Example 29 Oil Suspension N - [(4-Methoxy-6-methylpyrimidin-2-yl) -amino-carbonyl] -2-methylbenzenesulfonamide 35%

Blanding af polyolcarboxylsyreestere og olieopløselige jordoliesulfonater 6%Mixture of polyol carboxylic acid esters and oil-soluble petroleum sulfonates 6%

Xylen 59%Xylene 59%

Bestanddelene blandes og formales i en sandmølle til 30 dannelse af partikler, der i alt væsentligt er mindre end 5 jum. Produktet kan anvendes direkte, strækkes med olier eller emulgeres i vand.The ingredients are mixed and ground in a sand mill to form particles substantially less than 5 microns. The product can be used directly, stretched with oils or emulsified in water.

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Eksempel 30 Fugtepulver N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)- aminocarbonyl]benzensulfonamid 80%Example 30 Moisturizing Powder N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide 80%

Natriumalkylnaphthalensulfonat 2% 5Sodium alkyl naphthalenesulfonate 2% 5

Natriumligninsulfonat 2%Sodium lignin sulfonate 2%

Syntetisk amorft siliciumdioxid 3%Synthetic amorphous silica 3%

Kaolinit 13%Kaolinite 13%

Bestanddelene blandes, formales i en hammermølle ind-til det faste stof har en størrelse på i alt væsentligt mindre end 50 ^im, hvorefter der genblandes og emballeres.The ingredients are mixed, ground in a hammer mill until the solid has a size of substantially less than 50 µm, after which it is re-mixed and packaged.

Eksempel 31 Fugtepulver N-[(4,6-dimethyl-l,3,5-triazin-2-yl)-amino- carbonyljbenzensulfonamid 50%Example 31 Moist Powder N - [(4,6-Dimethyl-1,3,5-triazin-2-yl) -aminocarbonyl] benzenesulfonamide 50%

Natriumalkylnaphthalensulfonat 2%Sodium alkyl naphthalenesulfonate 2%

Lavviskos methylcellulose 2%Low viscous methyl cellulose 2%

Diatoméjord 46%Diatomaceous earth 46%

Bestanddelene blandes, formales groft i en hammermølle, 20 hvorefter der foretages formaling i en luftmølle til dannelse af partikler, der i alt væsentligt har en diameter på mindre end 10 pm. Produktet genblandes inden emballering.The ingredients are mixed, coarsely ground in a hammer mill, and then milled in an air mill to form particles having a diameter of substantially less than 10 µm. The product is remixed before packaging.

Eksempel 32 25 GranulatExample 32 Granules

Fugtepulver ifølge eksempel 31 5%Moisturizing Powder of Example 31 5%

Attapulgitgranulat (0,84-0,42 mm) 95%Attapulgite granules (0.84-0.42 mm) 95%

En opslæmning af fugtepulveret indeholdende omtrentlig 25% faststof sprøjtes på overfladen af attapulgitgranulatet 30 i et dobbeltkegleblandeapparatur. Granulatet tørres og emballeres .A slurry of the moisture powder containing approximately 25% solids is sprayed onto the surface of the attapulgite granulate 30 in a double cone mixer. The granulate is dried and packaged.

35 o 51 14934335 o 51 149343

Eksempel 33 Ekstruderede pellets N-[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-aminocarbonyl]-2-chlorbenzensulfonamid 25%Example 33 Extruded Pellets N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide 25%

Vandfri natriumsulfat 10% 5 Rå calciumligninsulfonat 5%Anhydrous sodium sulfate 10% 5 Crude calcium lignin sulfonate 5%

Natriumalkylnaphthalensulfonat 1%Sodium alkyl naphthalenesulfonate 1%

Calcium/magnesiumbentonit 59%Calcium / magnesium bentonite 59%

Bestanddelene blandes, formales i en hammermølle og fugtes derpå med ca. 12% vand. Blandingen ekstruderes i 10 form af cylindre med en diameter på ca. 3 mm, som derpå afskæres til dannelse af pellets med en længde på ca. 3 mm.The ingredients are mixed, ground in a hammer mill and then moistened with approx. 12% water. The mixture is extruded in the form of cylinders having a diameter of approx. 3 mm, which is then cut to form pellets having a length of approx. 3 mm.

Disse kan anvendes direkte efter tørring, eller de tørrede pellets kan knuses, således at produktet passerer en sigte med maskevidde på 0,84 mm. Granulatet, som tilbageholdes på 15 en sigte med maskevidde 0,42 mm, kan emballeres til anven delse, og de fine partikler recirkuleres.These can be used directly after drying or the dried pellets can be crushed so that the product passes a sieve with a mesh width of 0.84 mm. The granulate, which is retained on a sieve of mesh size 0.42 mm, can be packaged for use and the fine particles recycled.

Eksempel 34 Oliesuspension 20 N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)-amino carbonyl 1-2-chlor-5-methoxybenzensulfonamid 25%Example 34 Oil Suspension 20 N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -amino carbonyl 1-2-chloro-5-methoxybenzenesulfonamide 25%

Polyoxyethy1ensorbitolhexaoleat 5 % Højaliphatisk carbonhydridolie 70%Polyoxyethylene sorbitol hexa oleate 5% High aliphatic hydrocarbon oil 70%

Bestanddelene formales i en sandmølle, indtil de faste 25 partikler har en størrelse på mindre end ca. 5 jum. Den frem komne suspension kan anvendes direkte, dog fortrinsvis efter strækning med olier eller emulgering i vand.The ingredients are ground in a sand grinder until the solid 25 particles have a size of less than approx. 5 pm The resulting suspension can be used directly, but preferably after stretching with oils or emulsifying in water.

Eksempel 35 Fugtepulver 3° N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)-aminocarbonyl] -2-chlorbenzensulf onamid 20%Example 35 Moisturizing Powder 3 ° N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide 20%

Natriumalkylnaphthalensulfonat 4%Sodium alkyl naphthalenesulfonate 4%

Natriumligninsulfonat 4%Sodium lignin sulfonate 4%

Lavviskos methylcellulose 3% 35 Attapulgit 69% o 52 149343Low viscous methyl cellulose 3% Attapulgit 69% o 52 149343

Bestanddelene blandes omhyggeligt. Efter formaling i en hammermølle til dannelse af partikler, der i alt væsentligt har en størrelse på under 100 um, genblandes materialet og sigtes gennem en sigte med maskeåbning 0,3 mm, 5 hvorpå produktet emballeres.The ingredients are mixed thoroughly. After grinding in a hammer mill to form particles having substantially a size less than 100 µm, the material is re-mixed and sieved through a screen having a mesh opening of 0.3 mm, upon which the product is packaged.

Eksempel 36 Oliesuspension N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)-amino-10 carbonyl]-benzensulfonamid 35%Example 36 Oil Suspension N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -amino-carbonyl] -benzenesulfonamide 35%

Blanding af polyolcarboxylsyreestere og olieopløselige jordoliesulfonater 6%Mixture of polyol carboxylic acid esters and oil-soluble petroleum sulfonates 6%

Xylen 59%Xylene 59%

Bestanddelene kombineres og formales i en sandmølle - til dannelse af partikler med en størrelse på i alt væsentligt under 3 pm. Produktet kan anvendes direkte, strækkes med olier eller emulgeres i vand.The ingredients are combined and ground in a sand mill - to form particles with a size substantially below 3 microns. The product can be used directly, stretched with oils or emulsified in water.

Eksempel 37 2Q Højkoncentreret præparat N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)-amino-carbonyl]benzensulfonamid 99%Example 37 2Q High Concentrated Preparation N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -amino-carbonyl] benzenesulfonamide 99%

Siliciumdioxidaerogel 0,5%0.5% silica gel

Syntetisk amorft siliciumdioxid 0,5%Synthetic amorphous silica 0.5%

Bestanddelene blandes og formales på en hammermølle 25 til dannelse af et materiale, der i alt væsentligt passerer en sigte med en maskeåbning 0,3 mm. Koncentratet kan formuleres yderligere om nødvendigt.The components are mixed and ground on a hammer mill 25 to form a material which substantially passes a sieve with a mesh opening of 0.3 mm. The concentrate can be further formulated if necessary.

Eksempel 38 30Example 38 30

Granulat med lav styrke N-[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-aminocarbonyl]-2-chlor-5-methoxybenzen-sulfonamid 1% Ν,Ν-dimethylf ormamid 9% 35 Attapulgitgranulat (0,84-0,42 mm) 90%Low Strength Granules N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide 1% Ν, Ν-dimethylformamide 9 % 35 Attapulgite granules (0.84-0.42 mm) 90%

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Den aktive bestanddel opløses i opløsningsmidlet, og opløsningen sprøjtes på støvfrit granulat i et rota-tionsblandeapparatur. Efter at sprøjtning af opløsningen er afsluttet, kører blandeapparatet videre i en kort tid, 5 hvorefter granulatet emballeres.The active ingredient is dissolved in the solvent and the solution is sprayed onto dust-free granules in a rotary mixing apparatus. After spraying of the solution is complete, the mixer runs for a short time, after which the granulate is packaged.

Eksempel 39 Vandig suspension N-[(4,6-dimethyl-l,3,5-triazin-2-yl)-amino-10 carbonyl]-benzensulfonamid 40%Example 39 Aqueous suspension N - [(4,6-dimethyl-1,3,5-triazin-2-yl) -amino-carbonyl] -benzenesulfonamide 40%

Polyacrylsyrefortykkelsesmiddel 0,3%Polyacrylic Acid Thickener 0.3%

Dodecylphenolpolyethylenglycolether 0,5%Dodecylphenol polyethylene glycol ether 0.5%

Dinatriumphosphat 1%Disodium phosphate 1%

Mononatr iumphosphat 0,5% 15 Polyvinylalkohol 1,0%Monosodium phosphate 0.5% Polyvinyl alcohol 1.0%

Vand 56,7%Water 56.7%

Bestanddelene blandes og formales i en sandmølle til dannelse af partikler, der i alt væsentligt har en størrelse på mindre end 5 ^im.The ingredients are mixed and ground in a sand mill to form particles having substantially a size of less than 5 µm.

2020

Eksempel 40 Opløsning N-[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)--aminocarbonyl]-2-chlorbenzensulfonamid--natriumsalt 5% 25 Vand 95%Example 40 Solution N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide - sodium salt 5% Water 95%

Saltet sættes direkte til vandet under omrøring til dannelse af opløsningen, der derpå kan emballeres med henblik på anvendelse. 1 35The salt is added directly to the water with stirring to form the solution which can then be packaged for use. 1 35

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Eksempel 41 Granulat N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)-amino- carbonyl]-2,5-dimethoxybenzensulfonamid 80% 5 Fugtemiddel 1% Rå ligninsulfonatsalt indeholdende 5-20% af de naturlige sukkerarter 10%Example 41 Granulate N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2,5-dimethoxybenzenesulfonamide 80% Wetting agent 1% Raw lignin sulfonate salt containing 5-20% of the natural sugars 10%

Attåpulgitler 9%Atta Pulgitler 9%

Bestandde.lene blandes og formales, således at de passerer en 100 mesh-sigte. Dette materiale sættes derpå til et 10 fluid bed granuleringsapparatur, hvor luftstrømmen indstilles til forsigtig fluidisering af materialet, og en fin sprøjtetåge af vand sprøjtes på det fluidiserede materiale. Fluidisering en og sprøjtningen fortsættes, indtil der er dannet granulat af den ønskede størrelse. Derpå afbrydes sprøjt-15 ningen, men fluidiseringen fortsættes, eventuelt under opvarmning, indtil vandindholdet er formindsket til det ønskede niveau, sædvanligvis mindre end 1%. Materialet udtages derpå, sigtes til det ønskede størrelsesområde, sædvanligvis 1410-149 um og emballeres med henblik på anvendelse.The components are mixed and ground to pass a 100 mesh screen. This material is then added to a fluid bed granulation apparatus where the air flow is adjusted to gently fluidize the material and a fine spray of water is sprayed onto the fluidized material. Fluidization and spraying are continued until granules of the desired size are formed. The spraying is then interrupted, but the fluidization is continued, optionally with heating, until the water content is reduced to the desired level, usually less than 1%. The material is then removed, sieved to the desired size range, usually 1410-149 µm and packaged for use.

2020

Eksempel 42 Lavstyrkegranulat N-[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)- -aminocarbonyl]-2-chlorbenzensulfonamid 0,1% 25 Attapulgitgranulat (0,84-0,42 mm) 99,9%Example 42 Low Strength Granules N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide 0.1% Attapulgite granulate (0.84-0.42 mm 99.9%

Den aktive bestanddel opløses i et opløsningsmiddel, og opløsningen sprøjtes på støvfrit granulat i et dobbelt- kegleblandeapparatur. Efter at sprøjtning af opløsningen er afsluttet, opvarmes materialet til fordampning af opløsnings- 30 midlet. Materialet henstilles til afkøling, hvorefter det emballeres.The active ingredient is dissolved in a solvent and the solution is sprayed onto dust-free granules in a double cone mixer. After spraying of the solution is complete, the material is heated to evaporate the solvent. The material is left to cool and then packaged.

3535

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Eksempel 43 Fugtepulver N- [ (4-methoxy-6-methyl-l,3,5-triazin-2-yl)-aminocarbonyl]-2-chlor-5-methoxybenzen-sulfonamid 95% 5 Dioctylnatriumsulfosuccinat 0,1%Example 43 Moist powder N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide 95% Dioctyl sodium sulfosuccinate 0.1%

Syntetisk finpulveriseret siliciumdioxid 4,9%Synthetic fine powder silica 4.9%

Bestanddelene blandes og formales på en hammermølle til dannelse af partikler med en størrelse på i alt væsentligt under 100 um. Materialet sigtes gennem en US 10 sigte nr. 50, hvorefter det emballeres.The ingredients are mixed and ground on a hammer mill to form particles of substantially less than 100 µm. The material is sieved through a US 10 sieve No. 50, after which it is packaged.

Eksempel 44 Fugtepulver N-[(4-methoxy-6-methyl—1,3,5-triazin-2-15 -yl)aminocarbonyl]-2-chlorbenzen- sulfonamid 40%Example 44 Moisturizing Powder N - [(4-methoxy-6-methyl-1,3,5-triazin-2-15-yl) aminocarbonyl] -2-chlorobenzene sulfonamide 40%

Natriumligninsulfonat 20%Sodium lignin sulfonate 20%

Montmorillonitler 40%Montmorillonitler 40%

Bestanddelene blandes omhyggeligt, formales groft på 20 en hammermølle og derpå på en luftmølle til dannelse af par tikler, der stort set har en størrelse på mindre end 10 pti. Materialet genblandes og emballeres derpå;The ingredients are thoroughly mixed, coarsely milled on a hammer mill and then on an air mill to form pairs of ticks having a size of less than 10 pti. The material is then re-mixed and packaged;

Forbindelserne med formlen I kan formuleres under anvendelse af de i eksempel 15-44 anførte fremgangsmåder.The compounds of formula I can be formulated using the procedures set forth in Examples 15-44.

2g Forbindelserne med formlen I er anvendelige som herbi cider, de kan anvendes enten præ- eller postemergent til bekæmpelse af uønsket vegetation i områder uden afgrøder samt til selektiv ukrudtsbekæmpelse i visse afgrøder, f.eks. hvede. Nogle af disse forbindelser kan anvendes til præ-30 og/eller postemergent bekæmpelse af cyperus i afgrøder såsom bomuld, majs og ris. Ved rigtige valg af mængde og anvendelsestidspunkt, kan forbindelserne ifølge opfindelsen anvendes til gunstig modificering af plantevækst.2g The compounds of formula I are useful as herbicides, they can be used either pre- or post-emergence to control undesirable vegetation in areas without crops and for selective weed control in certain crops, e.g. wheat. Some of these compounds can be used for pre-30 and / or post-emergence control of cypress crops in crops such as cotton, maize and rice. By properly selecting the amount and time of application, the compounds of the invention can be used to favorably modify plant growth.

Den nøjagtige mængde af forbindelsen med formlen I, 35 som skal anvendes i en given situation, vil variere afhængigt af det tilsigtede slutresultat, den involverede anven- 149343 56The exact amount of the compound of formula I, 35 to be used in a given situation will vary depending on the intended end result, the use involved.

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delse, ukrudtsarten som skal bekæmpes, jordtypen, præparatet og anvendelsesmåden, vejrbetingelserne og lignende faktorer. Da så.mange variable har indflydelse, er det ikke muligt at angive en anvendelsesmængde, som er egnet i alle 5 situationer. Stort set anvendes de her omhandlede forbindelcrop, the type of weed to be controlled, the soil type, the composition and method of application, the weather conditions and similar factors. Since so many variables have an influence, it is not possible to specify a range of uses which is suitable in all 5 situations. Broadly speaking, the compound herein is used

ser i mængder på ca. 0,005 til 20 kg/ha, fortrinsvis 0,01-10 kg/ha. De mindre mængder i dette interval vælges sædvanligvis på lette jorde, til selektiv ukrudtsbekæmpelse i afgrøder eller i situationer, hvor den maksimale virkning 10 ikke er nødvendig. Nogle af forbindelserne med formel Ilooks in quantities of approx. 0.005 to 20 kg / ha, preferably 0.01-10 kg / ha. The smaller amounts in this range are usually selected on light soils, for selective weed control in crops or in situations where maximum effect 10 is not required. Some of the compounds of formula I

kan anvendes i meget små mængder til plantevækstmodificering, men større mængder kan også være anvendelige, afhængigt af faktorer såsom den pågældende afgrøde og behandlingstidspunktet .may be used in very small amounts for plant growth modification, but larger amounts may also be applicable, depending on factors such as the crop concerned and the time of treatment.

15 Forbindelserne med formel I kan kombineres med andre herbicide forbindelser og er især anvendelige i kombination med 3-(3,4-dichlorphenyl)-1,1-dimethylurinstof, triazinerne såsom 2-chlor-4-(ethylamino)-6-(isopropylamino)-s-triazin, uracilerne såsom 5-brom-3-sec-butyl-6-methyluracil, 20 N-(phosphonomethyl)glycin, 3-cyclohexyl-l-methyl-6-dime-thylamino-s-triazin-2,4(1H,3H)-dion, N,N-dimethyl-2,2-di-phenylacetamid, 2,4-dichlorphenoxyeddikesyre og dermed nært beslægtede forbindelser, 4-chlor-2-butynyl-3-chlorphenylcarb-amat ("Carbyni^1), diisopropylthiolcarbamidsyreester af 25 2,3-dichlorallylalkohol ("AvadejP^')y diisopropylthiolcarb- amidsyre, S-(2,3,3-trichlorallyl)ester ("Avadej^ BW), ethyl-N-benzoyl-N-(3,4-dichlorphenyl)-2-aminopropionat ("Suffix®'), l,2-dimethyl-3,5-diphenylpyrazoliummethylsulfat ("Avengi®"), methyl-2-[4-(2,4-dichlorphenoxy)-phenoxy]-pro-30 pionat ("Hoeloii^'), 4-amino-6-tert.butyl-3-(methylthio)- -l,2,4-triazin-5(4H)-on ("Lexone"), 3-(3,4-dichlorphenyl)--1-methoxy-l-methylurinstof ("Lorox"), 3-isopropyl-lH--2,l,3-benzothiadiazin-(4)-3H-on-2,2-dioxid, α,α,α-tri-fluor-2,6-dinitro-N,N-dipropyl-p-toluidin, 1,1'-dimethyl-35 -4,4'-bipyridiniumion-mononatriummethanarsonat, 2-chlor- -2',e'-diethyl-imethoxymethyljacetanilid og 1,1-dimethyl-3--(a,α,α-trifluor-m-tolyl)-urinstof ("Cotorari^') .The compounds of formula I can be combined with other herbicidal compounds and are particularly useful in combination with 3- (3,4-dichlorophenyl) -1,1-dimethylurea, the triazines such as 2-chloro-4- (ethylamino) -6- (isopropylamino) ) -s-triazine, the uracils such as 5-bromo-3-sec-butyl-6-methyluracil, N- (phosphonomethyl) glycine, 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2, 4 (1H, 3H) -dione, N, N-dimethyl-2,2-diphenylacetamide, 2,4-dichlorophenoxyacetic acid and closely related compounds, 4-chloro-2-butynyl-3-chlorophenylcarbamate ("Carbyni 1), diisopropylthiolcarbamic acid ester of 2,3-dichloroallyl alcohol ("AvadejP") y diisopropylthiolcarbamic acid, S- (2,3,3-trichloroallyl) ester ("Avadej ^ BW), ethyl-N-benzoyl-N- (3,4-dichlorophenyl) -2-aminopropionate ("Suffix®"), 1,2-dimethyl-3,5-diphenylpyrazolium methylsulfate ("Avengi®"), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propionate ("Hoelii"), 4-amino-6-tert.butyl-3- (methylthio) -1,2,4-triazine-5 (4H) -one ("Lexone" ), 3- (3,4-dichlorophenyl) -1-methox yl-methylurea ("Lorox"), 3-isopropyl-1H-1,2,1,3-benzothiadiazine- (4) -3H-one-2,2-dioxide, α, α, α-trifluoro-2, 6-dinitro-N, N-dipropyl-p-toluidine, 1,1'-dimethyl--4,4'-bipyridinium ion monosodium methanarsonate, 2-chloro-2 ', e'-diethylimethoxymethyljacetanilide and 1.1 -dimethyl-3- (α, α, α-trifluoro-m-tolyl) urea ("Cotorari").

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De her omhandlede forbindelsers virkning beskrives nærmere i nedenstående væksthusforsøg. Forsøget beskrives i detaljer, og de fremkomne resultater er anført i forbindelse dermed.The effect of these compounds is described in more detail in the greenhouse experiments below. The experiment is described in detail and the results obtained are stated in connection therewith.

5 Frø af fingeraks (Digitaria sp.), hanespore (Eschi- nochloa crusgalli), flyvehavre (Avena fatua), Cassia tora, Ipomoea sp., brodfrø (Xanthium sp.), durra, majs, sojabønne, ris, hvede og cyperusknoIde lægges i et vækstmedium og behandles præemergent med forsøgsforbindelserne opløst 10 i et ikke-phytotoksisk opløsningsmiddel. Samtidig sprøjtes bomuldsplanter med fire blade (inclusive kimbladene), krybbønner med det tredje tredelte blad udfoldet, fingeraks med to blade, hanespore med to blade, flyvehavre med et blad, cassia med tre blade (inclusive kimbladene), 15 Ipomoea med fire blade (inclusive kimbladene), brodfrø med fire blade (inclusive kimbladene), durra med tre blade, majs med tre blade, sojabønne med to kimblade, ris med to blade, hvede med et blad og cyperus med tre-fem blade. De behandlede planter og kontrolplanter holdes i et væksthus 20 i 16 dage, hvorefter alle plantesorterne sammenlignes med kontrolplanter, og der foretages visuel bedømmelse for respons på behandlingen.5 Flax seeds (Digitaria sp.), Male spores (Eschi-nochloa crusgalli), oats (Avena fatua), Cassia tora, Ipomoea sp., Bread seeds (Xanthium sp.) in a growth medium and treated preemergence with the test compounds dissolved in a non-phytotoxic solvent. At the same time, cotton plants are sprayed with four leaves (including the gum leaves), creeping beans with the third three-leaf leaf unfolded, finger axis with two leaves, male groove with two leaves, flying oats with one leaf, cassia with three leaves (including the gum leaves), 15 Ipomoea with four leaves (inclusive the seedlings), four-seeded bread seeds (including the seedlings), three-leaf sorghum, three-leaf corn, two-seeded soybean, two-leaf rice, one-leaf wheat, and three-five-leaf cyperus. The treated plants and control plants are kept in a greenhouse 20 for 16 days, after which all plant species are compared with control plants and visual assessment is made for response to the treatment.

Virkningen af forsøgsforbindelserne afprøvet ved denne fremgangsmåde er anført i den efterfølgende tabel IX.The effect of the test compounds tested by this method is given in the following Table IX.

25 Planteresponset udtrykkes på følgende måde: 0 = ingen virkning & eller 10 = maksimal virkning B = svidning 30 C = chlorosis eller necrosis D = defoliering E = emergensinhibering 6F = forsinket blomstring G = vækstretardering 35The plant response is expressed as follows: 0 = no effect & or 10 = maximum effect B = staining 30 C = chlorosis or necrosis D = defoliation E = emergence inhibition 6F = delayed flowering G = growth retardation 35

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Krybbønne 9C 9CCreeping Bean 9C 9C

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Durra 3C 3ϋ, 9GDurra 3C 3ϋ, 9G

Majs 9C 9CCorn 9C 9C

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Cassia 10C 50Cassia 10C 50

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Ipomoea 10E 10CIpomoea 10E 10C

Brodfrø 9G 10CBread seeds 9G 10C

Cassia 9G 100Cassia 9G 100

Cyperus 9G OCyperus 9G O

o 182 149363o 182 149363

Forbindelsernes anvendelse til selektiv ukrudtsbekæmpelse i hvede illustreres i nedenstående fire væksthusforsøg (test A, B, C og D).The use of the compounds for selective weed control in wheat is illustrated in the four greenhouse experiments below (tests A, B, C and D).

5 Test ATest A

To flade plastløgbakker med en diameter på 25 cm fyldes med gødet og kalkbehandlet Fallsington sandholdig lerjord. En bakke tilsåes med majs, durra og forskellige græsukrudtsarter. Den anden bakke tilsåes med sojabønne, Cyperus ro-10 tundus og forskellige bredbladede ukrudtsarter. Der anvendes følgende græsukrudtsarter og bredbladede ukrudtsarters Fingeraks (Digitaria sanguinalis), hanespore (Echinochloa crusgalli), flyvehavre (Avena fatua), Sorghum halepense, Setaria faberii,Two flat plastic onion trays with a diameter of 25 cm are filled with the fertilizer and lime-treated Fallsington sandy clay soil. A tray is sown with corn, sorghum and various grasses. The second tray is sown with soybean, Cyperus ro-10 tundus and various broadleaf weeds. The following grass weed species and broadleaf weed species are used Fingeraks (Digitaria sanguinalis), male spores (Echinochloa crusgalli), flying oats (Avena fatua), Sorghum tail brush, Setaria faberii,

Poa pratensis, Bromus secalinus, Brassica arvensis, Xanthium 15 pennsylvanicum, Amaranthus retroflexus, Aeschynomene virginica,Poa pratensis, Bromus secalinus, Brassica arvensis, Xanthium pennsylvanicum, Amaranthus retroflexus, Aeschynomene virginica,

Ipomoea hederacea, Cassia tora, Sida spinosa, Abutilon theophra-sti og Datura stramonium. Endvidere fyldes to papbægre med en diamter på 12,5 cm med behandlet jord. Det ene tilsåes med ris og hvede, og det andet med sukkerroe. De fire beholdere behand-20 ies præemergent, dvs. forbindelserne.sprøjtes på jordoverfladen inden spiring af frøene.Ipomoea hederacea, Cassia tora, Sida spinosa, Abutilon theophra path and Datura stramonium. In addition, two cardboard cups with a diameter of 12.5 cm are filled with treated soil. One is sown with rice and wheat, and the other with sugar beet. The four containers are treated pre-merger, ie. the compounds are sprayed onto the soil surface before germination of the seeds.

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Plastpotter med en diameter på 25 cm og fyldt med Fallsington sandholdig lerjord tilplantes med sojabønne, bomuld, lucerne, majs, ris, hvede, durra, Abutilon theophra-5 sti, Sesbania exaltata, Cassia tora, Ipomoea sp., Datura stramonium, Xanthium pennsylvanicum, Digitaria sp., Cyperus rotundus, Echinochloa crusgalli, Setaria faberii samt Avena fatua. Ca. 2 1/2 uge efter plantningen sprøjtes de unge planter og den omgivende jord overalt med forsøgsforbindelsen op-10 løst i et ikke-phytotoksisk opløsningsmiddel. 14 dage efter behandlingen sammenlignes alle planterne med ubehandlede kontrolplanter, og der foretages visuel bedømmelse for respons på behandlingen. Resultaterne er anført i den efterfølgende tabel XI.25 cm diameter plastic pots filled with Fallsington sandy clay soil are planted with soybean, cotton, alfalfa, maize, rice, wheat, sorghum, Abutilon theophra-5 path, Sesbania exaltata, Cassia tora, Ipomoea sp., Datura stramonium, Xanthium penns , Digitaria sp., Cyperus rotundus, Echinochloa crusgalli, Setaria faberii and Avena fatua. Ca. About 2 1/2 weeks after planting, the young plants and the surrounding soil are sprayed everywhere with the test compound dissolved in a non-phytotoxic solvent. 14 days after treatment, all plants are compared to untreated control plants and visual assessment is done for response to treatment. The results are given in the following Table XI.

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192 149343192 149343

OISLAND

Forbindelserne anvendes i et ikke-phytotoksisk opløsningsmiddel i form af samlede postemergente sprøjtninger af tilplantninger med hvede (højde 11 cm, 2-bladstadiet), 5 flyvehavre (Aveha fatua, højde 9 cm, 1-bladstadiet), Bromus tectorum (højde 5 cm, 1-bladstadiet), Bromus secalinus (højde 5 cm, 1-bladstadiet) , Alopecurus myosuroides (højde 3 cm, 1-bladstadiet), og Lolium multiflorum (højde 8 cm, 1-bladstadiet), og der foretages ligeledes præemergent 10 sprøjtning af tilsåninger med de samme planter. Alle tilplantninger og tilsåninger er foretaget i jordbakker med en diameter på 25 cm. Forsøgene gennemføres i væksthus, og planteresponsbedømmelsen foretages 5 uger efter påføringen. Resultaterne er anført i den efterfølgende tabel XII.The compounds are used in a non-phytotoxic solvent in the form of total post-emergence sprays of wheat plantings (height 11 cm, 2 leaf stage), 5 oats (Aveha fatua, height 9 cm, 1 leaf stage), Bromus tectorum (height 5 cm, 1-leaf stage), Bromus secalinus (height 5 cm, 1-leaf stage), Alopecurus myosuroides (height 3 cm, 1-leaf stage), and Lolium multiflorum (height 8 cm, 1-leaf stage), and preemergent spraying of sowings with the same plants. All plantings and sowings are made in soil trays with a diameter of 25 cm. The tests are carried out in a greenhouse and the plant response assessment is done 5 weeks after application. The results are set out in the following Table XII.

15 20 25 1 35 1A 93 A3 193 Μ i 0 η «η υ υ υ υ ^ ^ y Η·ΗΟΟΜ σι ca 03 Ο Ο <Ν 0 -Ρ J1 Μ (0 3 0) Ρ Ό 3 ο Ο U Ο Ο „ _ ο α> ρ ο ο ·~ι σ> oa °a ο ο %τ a 3 ο ω η ο <! >ι ε Μ tn 3 1 -S ο υαυ _ _ y η,ΟΗΟΟΠ ο3 οβ ο3 οοιη β Μ Λ S CQ Ο δ s φ β15 20 25 1 35 1A 93 A3 193 Μ i 0 η «η υ υ υ υ ^^ y Η · ΗΟΟΜ σι ca 03 Ο Ο <Ν 0 -Ρ J1 Μ (0 3 0) Ρ Ό 3 ο Ο U Ο Ο „_ Ο α> ρ ο ο · ~ ι σ> oa ° a ο ο% τ a 3 ο ω η ο <! > ι ε Μ tn 3 1 -S ο υαυ _ _ y η, ΟΗΟΟΠ ο3 οβ ο3 οοιη β Μ S CQ Ο δ s φ β

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Test DTest D

Forbindelserne påføres i et ikke-phytotoksisk opløsningsmiddel i form af samlede sprøjtninger af etablerede (postemergent) tilplantninger med hvede (højde 22 cm) , flyve-5 havre (Avena fatua, højde 12 cm), Bromus tectorum (højde 3 cm), Bromus secalinus (højde 5 cm), byg (højde 22 cm),The compounds are applied in a non-phytotoxic solvent in the form of total sprays of established (postemergent) wheat plantings (height 22 cm), fly oats (Avena fatua, height 12 cm), Bromus tectorum (height 3 cm), Bromus secalinus (height 5 cm), barley (height 22 cm),

Kochia scoparia (højde 5 cm), Matricaria inodora (højde 3 cm), Brassica arvensis (højde 7 cm), Eupatorium capilli-folium (højde 3 cm) og Polygonum concolvulus (højde 6 cm), "•0 og tillige foretages sprøjtning af præemergente tilsåninger med samme planter, der alle er sået i potter indeholdende jord. Forsøget gennemføres i et væksthus, og planterespons-bedøinmelsen foretages 4 uger efter påføringen. Resultaterne anføres i den efterfølgende tabel XIII.Kochia scoparia (height 5 cm), Matricaria inodora (height 3 cm), Brassica arvensis (height 7 cm), Eupatorium capilli-folium (height 3 cm) and Polygonum concolvulus (height 6 cm), "• 0 and also spraying of Preemergent seedlings with the same plants, all sown in pots containing soil The test is carried out in a greenhouse and the plant response assessment is made 4 weeks after application The results are given in the following Table XIII.

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0 202 149343 I nedenstående forsøg illustreres anvendelsen af de - her omhandlede forbindelser til bekæmpelse af cyperus.0 202 149343 The following experiments illustrate the use of the compounds of the present invention for the control of cypress.

Cyperusknolde (Cyperus rotundus) plantes i potter (5 knolde pr. potte) i en dybde på ca. 2,5 cm i 10 cm potter 5 indeholdende Fallsington sandholdig'lerjord. Forsøgsforbindelsen påføres i fom af en præemergent jordoverfladesprøjtning, en direkte knoldesprøjtning, jordinkorporering i de øverste 2,5 cm jord og postemergent sprøjtning på blade på planter med en højde på ca. 8-10 cm. Forbindelserne er 10 opløst i et egnet opløsningsmiddel og påføres med et sprøjterumfang på 560 liter/ha. Forsøgsforbindelsernes virkning på plantevæksten bedømmes visuelt 4 uger efter behandlingen. Resultaterne er anført i den efterfølgende tabel XIV.Cyperus tubers (Cyperus rotundus) are planted in pots (5 tubers per pot) at a depth of approx. 2.5 cm in 10 cm pots 5 containing Fallsington sandy clay soil. The test compound is applied in the form of a preemergent soil surface spray, a direct tuber spray, soil incorporation into the upper 2.5 cm soil and postemergent spray on leaves of plants with a height of approx. 8-10 cm. The compounds are dissolved in a suitable solvent and applied at a spray volume of 560 liters / ha. The effect of test compounds on plant growth is assessed visually 4 weeks after treatment. The results are set out in the following Table XIV.

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Nedenstående forsøg illustrerer de her omhandlede forbindelsers anvendelighed til selektiv bekæmpelse af Cyperus i afgrøder.The following experiments illustrate the utility of the compounds of this invention for selectively combating Cyperus in crops.

Plastbakker med en diameter på 25 cm forsynet med 5 polyethylenstykker fyldes med Fallsington sandet lerjord, og der plantes frø af følgende planter i en dybde på 2,5 cm i hver bakke: majs (Zea mays), sojabønne (Glycine max), ris (Oryza sativa), bomuld (Gossypium hirsutum) og Cyperusknolde (Cyperus rotundus). Hver forsøgsforbindelse opløses i et egnet 10 opløsningsmiddel og påføres præ- og postemergent i et sprøjterumfang på 560 liter/ha. Planterne, som behandles postemergent, har en højde på fra 6-14 cm på behandlingstidspunktet.Plastic trays with a diameter of 25 cm with 5 polyethylene pieces are filled with Fallsington sandy clay soil and seeds of the following plants are planted at a depth of 2.5 cm in each tray: maize (Zea mays), soybean (Glycine max), rice ( Oryza sativa), cotton (Gossypium hirsutum) and Cyperus tubers (Cyperus rotundus). Each test compound is dissolved in a suitable solvent and applied to pre- and postergens in a spray volume of 560 liters / ha. The plants that are treated post-emergence have a height of from 6-14 cm at the time of treatment.

4 uger efter behandlingen foretages visuel bedømmelse af forbindelsernes virkning på plantevæksten. Resultaterne er an-15 ført i den efterfølgende tabel XV.4 weeks after treatment, visual assessment of the effect of the compounds on plant growth is performed. The results are set out in the following Table XV.

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Det følgende forsøg illustrerer de her omhandlede forbindelsers anvendelse til bekæmpelse af visse vandukrudtsarter.The following experiment illustrates the use of the compounds of this invention to control certain water weed species.

Forbindelserne påføres i et ikke-fytotoksisk opløs-5 ningsmiddel i form af en samlet sprøjtning på små damme indeholdende vandhyacinth (Eichornia crassipes}, plantehøjde ca.The compounds are applied in a non-phytotoxic solvent in the form of an overall spray on small ponds containing water hyacinth (Eichornia crassipes), plant height approx.

25-30 cm. Forsøget gennemføres i et væksthus, og plantere-sponset bedømmes 4 uger efter påføringen. Dette forsøg illustrerer de her omhandlede forbindelsers anvendelighed til 10 bekæmpelse af vandukrudt. Resultaterne er anført i den efterfølgende tabel XVI.25-30 cm. The test is carried out in a greenhouse and the plant-sponsored is assessed 4 weeks after application. This experiment illustrates the utility of the compounds of this invention for the control of water weeds. The results are given in the following Table XVI.

15 20 25 1 3515 20 25 1 35

Tabel XVITable XVI

211 149343211 149343

Planterespons-_bedømmelse_ Mængde Vand- _Forbindelse_kg/ha_hyacinth - / _\ 0 yN=C%Plant Response _ Rating_ Amount of Water _ Compound_kg / ha_hyacinth - / _ \ 0 yN = C%

/ C Λ V-SO^-NH-C-NH-C^ CH 1/32 9G/ C Λ V-SO ^ -NH-C-NH-C ^ CH 1/32 9G

22/ > W22 /> W

ClCl

/"~\ O N ,0-CH, 1/32 9G2C/ "~ \ O N, 0-CH, 1/32 9G2C

/ (^^V-SO -NH-C-NH-CV (SO) -NH-C-NH-C

Vrv il L 1/16 9CVrv il L 1/16 9C

V v CH3 —V v CH3 -

Η3°_0ν N- 1/16 9GΗ3 ° _0ν N- 1/16 9G

^c-n^ o AZT\^ c-n ^ o AZT \

HC^ VC-NH-C-NH-SO„—( C )) 1/8 9GHCl VC-NH-C-NH-SO 2 - (C) 1/8 9G

SC = N/ 2 \W/SC = N / 2 \ W /

/ \_/ 1/4 9G4C/ \ _ / 1/4 9G4C

H3c 1/2 9G4CH3c 1/2 9G4C

H3COv Cl\_vH3COv Cl \ _v

HC C-NH-C-NH-SO- _/ ( )\ 1/32 9G9CHC C-NH-C-NH-SO- _ / () \ 1/32 9G9C

2-yjy »/ 2 *3“v V_2-yjy »/ 2 * 3“ v V_

/2 9 /z~x\ 1/32 9G1C/ 2 9 / z ~ x \ 1/32 9G1C

HC C-NH-C-NH-SO —( ( ) ) \:=νχ \_y 1/f16 9Glc H3c/HC C-NH-C-NH-SO - (()) \: = νχ \ _y 1 / f16 9Glc H3c /

yCHY CH

S O N-c' J 1/32 9GS O N-c 'J 1/32 9G

/V » ^ ^/ V »^^

HC C- S0o “NH-C-NH-C CHHC C-SOO “NH-C-NH-C CH

h<?_Jh ^16 9Gh <? _ Jh ^ 16 9G

Tabel XVI (fortsat) 212 149343Table XVI (continued) 212 149343

Planterespons-_bedømmelse_ Mængde Vand- _ Forbindelse_kg/ha_hyacinthPlant response-_ rating_ Quantity Water- _ Compound_kg / ha_hyacinth

CHCH

o N— C 3 1/32 9G5Co N— C 3 1/32 9G5C

SO -NH-C-NH-C* > HC C nN=C 'SO -NH-C-NH-C *> HC C nN = C '

HC-CHHC-CH

H3<Sc-n o C1/7^\ 1/32 9GH3 <Sc-n o C1 / 7 ^ \ 1/32 9G

HC^ VC-NH-C-NH-SO--/ /) \HCl VC-NH-C-NH-SO -

nc = n/ V^v/ 1/16 9G2Cnc = n / V ^ v / 1/16 9G2C

H3C'H3C '

„„ H.CO"" H.CO

H C0N 3 i_ ^C-N^ O /^-x\H C0N 3 i_ ^ C-N ^ O / ^ - x \

Hc' C-NH-C-NH-SO,./ ( ) > 1/32 9GHc 'C-NH-C-NH-SO, ./ ()> 1/32 9G

SC=N/ 2\W/ H3CO^ ^och3 0 ^N-CnSC = N / 2 \ W / H 3 CO 2 and 30 N-Cn

/ V- SO_ -NH-C-NH-C^ ^CH 1/32 9G/ V- SO_ -NH-C-NH-C ^^ CH 1/32 9G

CH3 (O^ "CH3 (O

Cl CH3Cl CH3

/Q\s02-NH-C-NH-<y ^-0-αΗ3 l/32 9G9C/ Q \ s02-NH-C-NH- <y ^ -0-αΗ3 l / 32 9G9C

\_/ N N\ _ / N N

^Cl V^ Cl V

0-CH30-CH3

Tabel XVI (fortsat) 213 149343Table XVI (continued) 213 149343

Planterespons-_bedømmelse_ Mængde Vand- _Forbindelse_kg/ha_ hyacinthPlant Response _ Rating_ Amount of Water _Connection_kg / ha_ Hyacinth

H COH CO

H3COv )-v /c — N O /^r\H3 COv) -v / c - N O / R

N/ NNC-NH-C-NH-S0o -( ( ) > 1/32 &GN / NNC-NH-C-NH-SOO - (()> 1/32 & G

2 \W/ H CO/ ' \ och3 H 00 >“»* o- /~\2 \ W / H CO / '\ and3 H 00>' »* o- / ~ \

W ^C-NH-C-NH-SO„—/ () ) 1/32 8GW C-NH-C-NH-SO 2 - / ()) 1/32 8G

VC = N'' U3C-o' '-' — H3C°n \-v ,c = nn o A-T\VC = N '' U3C-o '' - '- H3C ° n \ -v, c = nn o A-T \

N C-NH-C-NH-SO„-( ( ) > 1/32 &G&CN C-NH-C-NH-SO + - (()> 1/32 & G & C

*C-n' 2\V/ H C" \ och3* C-n '2 \ V / H C "\ och3

ClCl

Nx o V-\ 1/32 9G7CNx o V- \ 1/32 9G7C

H3C-°"f SC-NH-C-NH-S02-/Q\ 1/16 9G7CH3C- ° f SC-NH-C-NH-SO2- / Q \ 1/16 9G7C

N N \_/ SC* 0h3 23.4 149363 oN N \ _ / SC * 0h3 23.4 149363 o

Udover den herbicide virkning har de her omhandlede forbindelser tillige gunstig modificerende virkning på vask-sten af visse plantesorter. Anvendelsesmængder (sædvanligvis 0,01-1,0 kg/ha) og anvendelsestidspunkt vælges afhængigt af 5 plantesorterne med henblik på opnåelse af ønskede virkninger med minimal fytotoksicitet. Såvel den vegetative vækst som forplantningsvadesten kan reguleres. Nedenstående eksempler illustrerer virkningen på sukkerrør, durra, bahiagræs og andre græsser. I sukkerrør og durra fremkaldes en såkaldt 10 "kemisk modningsvirkning", der resulterer i et større udbytte af opløselige faste stoffer (overvejende sukkerarter).In addition to the herbicidal action, the compounds of this invention also have beneficial modifying effect on the washing stone of certain plant species. Amounts of application (usually 0.01-1.0 kg / ha) and time of use are selected depending on the plant species to obtain desired effects with minimal phytotoxicity. Both vegetative growth and reproductive growth can be regulated. The following examples illustrate the effect on sugar cane, sorghum, Bahia grass and other grasses. In sugar cane and sorghum a so-called "chemical maturation" is produced, resulting in a greater yield of soluble solids (predominantly sugars).

I mange andre græsarter begrænser disse forbindelser vækst og frøstilkudvikling, hvilket formindsker bevægelseskrav. Forbindelserne er tillige anvendelige til vækstbekæmpelse 15 af træukrudtsplanter og bladukrudtsplanter.In many other grass species, these compounds limit growth and seed growth, reducing movement requirements. The compounds are also useful for growth control 15 of tree weeds and leaf weeds.

Eksempel AExample A

Dværgsukkerrørsplanter med en alder på 6-8 måneder dyrkes med 3-5 stilke pr. cm potte (højde 1,5-3 m) og sprøj-20 tes med forsøgsforbindelsen (2 potter pr. forbindelse). Hver stilk måles til den højeste synlige bladkrave ved starten og afslutningen af forsøget for at bestemme virkningen på højdevæksten. Når stilkene høstes 5 uger efter behandlingen, ekstraheres saften fra stilkene, og de opløselige faste stof-25 fer bestemmes i midten af den øverste tredjedel, den midterste tredjedel og den nederste tredjedel af hver stilk. Resultaterne anføres i den efterfølgende tabel XVII. Det fremgår af resultaterne i tabel XVII, at i stilke behandlet med de her omhandlede forbindelser forøges mængden af opløselige 30 stoffer,og væksten begrænses i forhold til opløsningsmiddel-kontrolplanten (500 liter/ha vand plus overfladeaktivt stof "Tween" ® 20 i en mængde på 0,2%).Dwarf sugar cane plants with an age of 6-8 months are grown with 3-5 stems per year. cm pot (height 1.5-3 m) and sprayed with the test compound (2 pots per compound). Each stem is measured to the highest visible leaf collar at the start and end of the trial to determine the effect on height growth. When the stalks are harvested 5 weeks after treatment, the juice is extracted from the stalks and the soluble solids are determined in the middle of the upper third, middle third and lower third of each stalk. The results are given in the following Table XVII. The results in Table XVII show that in stems treated with the compounds of this invention, the amount of soluble 30 substances is increased and growth is limited relative to the solvent control plant (500 liters / ha of water plus surfactant "Tween" ® 20 in an amount of 0.2%).

3535

O Tabel XVIIO Table XVII

215 149343215 149343

Del af sukkerrørsstilk Vækst Neder- kg/ha (cm) ste_Midten TopPart of cane stem Growth Lower kg / ha (cm) ste_Midten Top

Cl Ρ°Β3 6 If 1 £§ S:.1 ta3 · _^CH3 0 N-Cl^ 3 0,25 15 18,1 18,9 13,4 10 U .VsO.-NH-C-NHC CH 1,0 6 19,9 20,4 15,8 v_y 2 w NCH3Cl Ρ ° Β3 6 If 1 £ § S: .1 ta3 · _ ^ CH3 0 N-Cl ^ 3 0.25 15 18.1 18.9 13.4 10 U .VsO.-NH-C-NHC CH 1 , 0 6 19.9 20.4 15.8 v_y 2 w NCH3

Opløsningsmiddelkontrol - 40 16,7 13,8 6,1 OCH, —Λ1 O ,Ν-c' 0,25 3 19,9 20,2 16,8 15 \\ /VsOo-NH-C-NHC N 1,0 4 18,8 19,9 16,6Solvent Control - 40 16.7 13.8 6.1 OCH, -1.1 O, Ν-c '0.25 3 19.9 20.2 16.8 15 µg / VsOo-NH-C-NHC N 1.0 4 18.8 19.9 16.6

• OCH3 Eksempel B• OCH3 Example B

20 Sukkerdurraplanter dyrkes med en plante pr. 15 cm potte til et stadium lige inden aksfremkomst, og der sprøjtes med de nedenfor anførte forbindelser. Der foretages visuel bedømmelse ca. 3 uger efter sprøjtningen. Efter 4 ugers forløb høstes planterne, og indholdet af opløselige faste stof-25 fer bestemmes i centret af den øverste del, den midterste del og den nederste del af hver stilk. Det fremgår af de i tabel XVIII anførte data, at det procentvise indhold af opløselige faste stoffer forøges, og væksten og blomstringen begrænses i stilke behandlet med de omhandlede forbindelser.20 Sugarcane plants are grown with one plant per year. 15 cm pot to a stage just before axis emergence, and the compounds listed below are sprayed. Visual assessment is carried out approx. 3 weeks after spraying. After 4 weeks, the plants are harvested and the content of soluble solids is determined in the center by the upper, middle and lower parts of each stalk. It is apparent from the data set out in Table XVIII that the percentage soluble solids content is increased and growth and flowering are restricted in stems treated with the compounds in question.

30 3530 35

Tabel XVIIITable XVIII

216 149343216 149343

Opløste faste stoffer udtrykt i % af kontrolværdier i forskellige dele _ af durrastilke 3-ugers - responsbedøm- Neder- _Forbindelse_kg/ha melse_ste_Midten TopDissolved solids expressed as% of control values in different parts _ of durable silk 3-week - response rating- Lower _Connection_kg / ha_melt_ste_Midten Top

CELCEL

0 N-Cy 1,0 9G,F,2X 114 132 69 / Λ-SO -NHC-NH-C CH 4,0 9G,F 115 128 '—' 'n=c' \ CH3 CH pCH, pj J O JSI-C 0,03 9G,F,3X 119 99 84 / Vso -NHC-NH-C ''CH 0,5 &G-F-3X 119 119 1120 N-Cy 1.0 9G, F, 2X 114 132 69 / Λ-SO -NHC-NH-C CH 4.0 9G, F 115 128 '-' 'n = c' \ CH3 CH pCH, p JO JSI -C 0.03 9G, F, 3X 119 99 84 / V 50 -NHC-NH-C '' CH 0.5 & G-F-3X 119 119 112

'—' N=C'-' N = C

'0B3'0B3

CHCH

O yN-Cx 1,0 8g,F,2x 114 140 96O yN-Cx 1.0 8g, F, 2x 114 140 96

L V SO.-NHC-NH-C 'CHL V SO.-NHC-NH-C 'CH

'—' N=€H'-' N = € H

CHCH

S. O N-c' 0,125 &G,F,1C 119 109 88 HC C-SO.-NH-C-NH-C CH 2,0 &G,F 122 115 66 u 11 Z v /S. O N-c '0.125 & G, F, 1C 119 109 88 HC C-SO.-NH-C-NH-C CH 2.0 & G, F 122 115 66 u 11 Z v /

HC-CH N=CHC-CH N = C

'CH3'CH3

,OCH, OCH

QO ^N=C 0,5 9G,F,2X 111 100 57 SO,-NHC-NH-C CH 2,0 &G,F,2X 118 105 59QO ^N = C 0.5 9G, F, 2X 111 100 57 SO, -NHC-NH-C CH 2.0 & G, F, 2X 118 105 59

'N-C'N-C

cl 'bcH3 CH.cl 'bcH3 CH.

/ 3/ 3

/=Λ 9 ,N=C/ = Λ 9, N = C

L ,VsO,-NHC-NH-C CH 0,5 7G 115 106 98 ^ 2 vc; OCH2CH3 ch3 ch3L, VsO, -NHC-NH-C CH 0.5 7G 115 106 98 ^ 2 vc; OCH2CH3 ch3 ch3

Mso -nhc-nh-/~%h °'125 9G'F'1C 139 115 140 ^-S02 NHC NH C^CH 0fS 9g,f,2C 147 129 146 \ CH3 ,CH /CH3 pj 6 O N-C 0,125 &G,F 113 113 114 - / \-S02-NHC-NH-C jCH 0,5 SG,F 120 113 121Mso -nhc-nh- / ~% h ° '125 9G'F'1C 139 115 140 ^ -S02 NHC NH C ^ CH 0fS 9g, f, 2C 147 129 146 \ CH3, CH / CH3 p6 O NC 0.125 & G , F 113 113 114 - / -SO 2 -NHC-NH-C jCH 0.5 SG, F 120 113 121

)— N=C) - N = C

CH3 ch3CH3 ch3

Tabel XVIII (fortsat) 217 149343Table XVIII (continued) 217 149343

Opløste faste stoffer udtrykt i % af kontrolværdier i forskellige dele af durrastilke_ 3-ugers responsbedøm- Neder- _Forbindelse_kg/ha melse_ste_Midten TopDissolved solids expressed as% of control values in different parts of durastilke_ 3-week response assessment- Lower _Connection_kg / ha measure_ste_Midten Top

F CHF CH

/=^ 0 N-C 0,125 &G,F,1C 127 127 136 (N Λ-SO -NH-C-NH-C CH 0,5 &G,F,1C 127 127 136N = C 0.125 & G, F, 1C 127 127 136 (N Λ-SO -NH-C-NH-C CH 0.5 & G, F, 1C 127 127 136

'—' N=C'-' N = C

VCH3 OCH, O N-C 0,25 &G,F 120 120 121 L Λ-SO -NHC-NH-C 'CH 1,0 &G,F 120 120 121VCH3 AND, O N-C 0.25 & G, F 120 120 121 L Λ-SO-NHC-NH-C 'CH 1.0 & G, F 120 120 121

'—S N=C- S N = C

• 'CH3• 'CH3

OCHOCH

/r^r\ O N-C 0,25 &G,F 120 113 107 (. Λ-SO -NHC-NH-C ‘‘CH 1,0 &G,F 113 113 107/ r ^ r \ O N-C 0.25 & G, F 120 113 107 (. Λ-SO-NHC-NH-C '' CH 1.0 & G, F 113 113 107

\—f N=C\ -F N = C

'och3'OCH3

Cl PH 3Cl PH 3

O ^N-CO ^ N-C

L N-SO -NHC-NH-C CH 0,5 6G,F,2X - 122L N-SO -NHC-NH-C CH 0.5 6G, F, 2X - 122

y—* N=Cy— * N = C

C1 CH3 OCH- /-r/OCH3 O ^N-c' <( Λ-SO -NHC-NH-C CH 0,125 9G,F,8X - 130 - y1* n=cC1 CH3 OCH- / -r / OCH3 O ^ N-c '<(Λ-SO-NHC-NH-C CH 0.125 9G, F, 8X - 130 - y1 * n = c

Cl OCH3 pi ,CH3Cl OCH3 pi, CH3

r=\ n N-Cr = \ n N-C

L N-SO.-NHC-NH-C 'CH 0,06 9G,F,2X - 139L N-SO.-NHC-NH-C 'CH 0.06 9G, F, 2X - 139

^ 2 W^ 2 W

\\

HH

Cl /CIi3Cl / CI3

O /(N-CO / (N-C

L /VsO^NHC-NH-C CH 0,06 &G,F,2U - 165 CH3L / V 50 O NHC-NH-C CH 0.06 & G, F, 2U - 165 CH3

Cl F /CH3Cl F / CH3

W O N-CW O N-C

(\ /Vso -NHC-NH-ς CH 0,06 &G,F,1X - 165(\ / V 50 -NHC-NH-CH CH 0.06 & G, F, 1X - 165

'—' N=C'-' N = C

ch3CH3

Tabel XVIII (fortsat) 218 149343Table XVIII (continued) 218 149343

Opløste faste stoffer udtrykt i % af kontrolværdier i forskellige dele af durrastilke 3-ugers respons- bedøm- Neder- _Forbindelse_kg/ha melse_ste_Midten Top „-i „ OCH_Dissolved solids expressed as% of control values in different parts of durra silk 3-week response assessment- Lower-compound_kg / ha measure_ste_Midten Top "-in" OCH_

W O N-CW O N-C

C /VSO.-NHC-NH-C CH 0,25 0 - 122C / VSO.-NHC-NH-C CH 0.25 0 - 122

'—' N=C'-' N = C

0CH3 /0CH3 QO N=Cn 0,03 &G,F,2X 119 112 116 SO -NHC-NH-C £E 0,125 &G,F,2X 135 111 105 'N-C 0,5 &G,F,2X 126 117 108 d ch30CH3 / 0CH3 QO N = Cn 0.03 & G, F, 2X 119 112 116 SO -NHC-NH-C £ E 0.125 & G, F, 2X 135 111 105 'NC 0.5 & G, F, 2X 126 117 108 d CH3

OCHOCH

O N-(( 0,125 5G,F,2X 116 107 101 L \-S0 -NHC-NH-C N 0,5 8G,F 115 107 113 '—' N=C 2,0 8G,F 118 107 113 °CH3O N - ((0.125 5G, F, 2X 116 107 101 L \ -S0 -NHC-NH-C N 0.5 8G, F 115 107 113 '-' N = C 2.0 8G, F 118 107 113 ° CH3

CHCH

O N-C 0,125 8G,F,3x 128 123 118 C VsOp-NHC-NH-C N 0,5 9G,F 143 124 105 N=C 2,0 9G,F 127 111 132O N-C 0.125 8G, F, 3x 128 123 118 C VsOp-NHC-NH-C N 0.5 9G, F 143 124 105 N = C 2.0 9G, F 127 111 132

OCHOCH

__ o JS-C 0,125 &G,F,1C 127 124 125 Λ A-SO^-NHC-NH-cf 'n 0,5 &G,F,2C 120 113 79 ' N=ctf 2,0 &G,F,2C 133 120 114 ch3 F = forsinket blomstring 219 149343 o__ o JS-C 0.125 & G, F, 1C 127 124 125 Λ A-SO ^ -NHC-NH-cf a 0.5 & G, F, 2C 120 113 79 'N = ctf 2.0 & G, F, 2C 133 120 114 ch3 F = delayed flowering 219 149343 o

Eksempel CExample C

Bahiagræsplanter (Paspalus notatum, Flugge) dyrket i 13 cm potter sprøjtes med de nedenfor i tabel XIX anførte forbindelser, når frøaksene netop er klar til at bryde frem.Bahia grass plants (Paspalus notatum, Flugge) grown in 13 cm pots are sprayed with the compounds listed below in Table XIX when the seed axes are just ready to break out.

5 Planterne har en højde på ca. 35 cm, og 3 potter sprøjtes over toppen (560 liter/ha) med hver anvendelsesmængde. De i den efterfølgende tabel XIX anførte resultater er registreret 45 dage efter behandlingen. De her omhandlede forbindelser retarderer væksten og undertrykker frøaksudvikling.5 The plants have a height of approx. 35 cm and 3 pots are sprayed over the top (560 liters / ha) with each application volume. The results given in the following Table XIX are recorded 45 days after treatment. The compounds of this invention retard growth and suppress seed growth.

1010

Tabel XIXTable XIX

45-dages Procentvis responsbe- undertrykkelse · 15 kg7ha dømmelse_af frøaks_ CH_ S O N-C 3 °'03 2G 10 HC C-S0„-NH-C-NH-C CH „'t Τ’ „ " " 2 W 0,5 3G'2U 90 HC CH v,H 1,0 3G,2U 100 20 ^-/™3 o «Τ’ 0,008 2g 0 O-S0,-OT-C-NH-C CH 3G 30 V V 2 ' ' 0,125 9G,1C,2U 95 ' 0,5 9g,2C,2U 95 CH345-day Percent response suppression · 15 kg7ha judging_of seed ax_ CH_ SO NC 3 ° '03 2G 10 HC C-SO '-NH-C-NH-C CH' 't Τ' '"" 2 W 0.5 3G' 2U 90 HC CH v, H 1.0 3G, 2U 100 20 ^ - / ™ 3 o «Τ '0.008 2g 0 O-S0, -OT-C-NH-C CH 3G 30 VV 2' '0.125 9G, 1C , 2U 95 '0.5 9g, 2C, 2U 95 CH3

OCHOCH

O n=C 3 0,008 2G 70 25 ^VsO^-NH-C-NH-C VCH 0,03 7G 70 \\ γ 2 *N_C* 0,125 &G,2C,2U 95O n = C 3 0.008 2G 70 25 VsO 2 -NH-C-NH-C VCH 0.03 7G 70 \ γ 2 * N_C * 0.125 & G, 2C, 2U 95

Cl 'CH 0,5 &G,3C,2U 100 1 35 0 220 149343Cl 'CH 0.5 & G, 3C, 2U 100 1 35 0 220 149343

De følgende forsøg tjener til yderligere illustrering af de her omhandlede forbindelsers biologiske virkning. Forsøgene illustrerer forbindelsernes herbicide virkning med selektivitet for to vigtige afgrødeplanter, ris og hvede.The following experiments serve to further illustrate the biological effect of the compounds of this invention. The experiments illustrate the herbicidal action of the compounds with selectivity for two important crop plants, rice and wheat.

5 Forsøgsforbindelsen påføres i et ikke-phytotoksisk opløsningsmiddel på jordpotter indeholdende frø af hybridris, japansk ris, Echinochloa crusgalli og Ipomoea sp. En forbindelse påføres ligeledes på hvede, Avena fatua, Bromus te-ctorum og Bromus secalinus. Etablerede beplantninger (post-10 emergens) af nogle eller alle ovennævnte planter omfattes ligeledes af forsøget. Planterne holdes i væksthus, og der foretages visuel planteresponsbedømmelse ca. 3 uger efter påføringen. Resultaterne er anført i den efterfølgende tabel XX.The test compound is applied in a non-phytotoxic solvent to soil pots containing seeds of hybrid rice, Japanese rice, Echinochloa crusgalli and Ipomoea sp. A compound is also applied to wheat, Avena fatua, Bromus teactorum and Bromus secalinus. Established plantings (post-10 emergence) of some or all of the above plants are also included in the experiment. The plants are kept in greenhouses and visual plant response assessment is carried out approx. 3 weeks after application. The results are given in the following Table XX.

15 20 25 1 35 149343 22115 20 25 1 35 149343 221

snujiBoes snmoag ^ SsnujiBoes snmoag ^ S

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•S• S

o stj: usueder o o o o A* _sjjpTjqÅH o o i oo st: usueder o o o o A * _sjjpTjqÅH o o i o

snujxBoøs snrnojg SsnujxBoose snrnojg S

um^oqoeq snrncag S § ajABqaAÅxg o roum ^ oqoeq snrncag S § ajABqaAÅxg o ro

OISLAND

θρθΛΗ O HθρθΛΗ O H

X , O O O UX, O O O U

X ω Βθοιποαι n a ο oo ηX ω Βθοιποαι n and ο oo η

GG

η 21 a) t? o u o uη 21 a) t? o u o u

^ jjj B^odSBUBH 10 <51 LD CTI^ jjj B ^ odSBUBH 10 <51 LD CTI

S sS s

Si t o uThey t o u

Rj su jfsUEdBf o cn o r*Rj su jfsUEdBf o cn o r *

Ok ST^pxjqÅH om ο ^ Ο) ΒΙ{/βθ[ η ^ η οοOk ST ^ pxjqÅH if ο ^ Ο) ΒΙ {/ βθ [η ^ η οο

1 NV SN1 NV SN

Η Η i—i ιΗ ro ro ΓΠ ro m g a °ϊοί °lol γ γ ηα a φ °| °=ί (0 2 2Η Η i — i ιΗ ro ro ΓΠ ro m g a ° ϊοί ° lol γ γ ηα a φ ° | ° = ί (0 2 2

ιΗ 0>) CNιΗ 0>) CN

m Ο Ο rri W Μm Ο Ο rri W Μ

2 Η I Η Η I2 Η I Η Η I

U οU ο

Claims (4)

149343 O Patentkrav .149343 O Patent Claims. 1. Sulfonamid-derivater med herbicid og plantevækstregulerende virkning, kendetegnet ved, at de har den almene formel 5 ; R1-SO2-NH-C—NH-R hvor R er1. Sulfonamide derivatives with herbicide and plant growth regulating effect, characterized in that they have the general formula 5; R1-SO2-NH-C-NH-R where R is 10. X N—( N—/ _(/ Λ eller 'ft Z ^Z10. X N— (N— / _ {/ Λ or 'ft Z ^ Z 15 R1 er R1 R2 3 _ -Q-r5 /Λ /A eller 00 ’R1 is R1 R2 3 -Q-r5 / Λ / A or 00 ' 20 R4 R5 R6 R7 R8 6 2 R og R hver for sig betyder hydrogen, fluor, chlor, brom, iod, C^-C4~alkyl, C^-C^-alkoxy, nitro, trifluormethyl, cyano, CH3S(0)n- eller CH3CI-I2S (0)η~,R 4 and R 5 R 6 R 7 R 8 6 2 R and R, respectively, represent hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano, CH n- or CH3 Cl-I2S (O) η ~, 25 R2 betyder hydrogen, fluor, chlor, brom eller methyl, 3 4 R betyder hydrogen, fluor, chlor, brom, C^_2-alkyl eller C^j-alkoxy, 5 R betyder hydrogen, fluor, chlor, brom, methvl eller methoxy, 6 r8 betyder hydrogen, methvl, chlor eller brom, 7 10 30. og R hver for sig betyder hydrogen, methyl, chlor eller brom, W og Q hver for sig betyder oxygen eller svovl, n er" 0, 1 eller 2, 8 X betyder hydrogen, chlor, brom, methyl, ethyl, C1_3~alkoxy, 35 trifluormethyl, CH3S- eller CH3OCH2-, og Z betyder methyl eller methoxy, eller agrikulturelt egnede salte deraf, 223 149343 o idet dog a) når R5 er forskellig fra hydrogen, er mindst én af sub-stituenterne R^, R^, R6 og R7 forskellig fra hydrogen, og mindst to af substituenterne R , R^, R° og Rf skal være 5 hydrogen, 5 3 4 6 b) når R er hydrogen og alle substituenterne R , R , R og 7 R er forskellig fra hydrogen, skal alle substituenter-3 4 6 7 ne R , R , R° og R/ være enten chlor eller methyl, og 3 7 c) når R og R begge betyder hydrogen, skal mindst én af 4 5 6 10 substituenterne R , R3 eller R være hydrogen.R 2 represents hydrogen, fluoro, chloro, bromo or methyl, R 4 represents hydrogen, fluoro, chloro, bromo, C 1-6 alkyl or C 1-6 alkoxy, R 5 represents hydrogen, fluoro, chloro, bromo, methyl or methoxy, 6 r8 means hydrogen, methyl, chlorine or bromine, 7 10 30. and R individually means hydrogen, methyl, chlorine or bromine, W and Q individually represent oxygen or sulfur, n is "0, 1 or 2 , 8 X represents hydrogen, chlorine, bromine, methyl, ethyl, C1-3 alkoxy, trifluoromethyl, CH3S or CH3OCH2-, and Z means methyl or methoxy, or agriculturally suitable salts thereof, however a) when R5 is other than hydrogen, at least one of the substituents R 1, R 2, R 6 and R 7 is different from hydrogen and at least two of the substituents R, R 2, R 2 and R f must be 5 hydrogen, 5 3 4 6 b) when R is hydrogen and all substituents R, R, R and 7 R are different from hydrogen, all substituents-3 4 6 7 ne R, R, R ° and R / must be either chlorine or methyl, and 3 7 c) when R and R both means hydrogen, at least one of the substituents R, R3 or R must be hydrogen. 2. Kemisk forbindelse ifølge krav 1, kendetegnet ved, at R^- betyder r3 R4Chemical compound according to claim 1, characterized in that R 2 - represents r 3 R 4 15 R5 R7 R6 3 R betyder hydrogen, fluor, chlor, brom, C -alkyl, C2_4--alkoxy, CH^S- eller CH^CI^S-,R 5 R 7 R 6 3 R means hydrogen, fluoro, chloro, bromo, C 1-6 alkyl, C 2-4 alkoxy, CH 2 S- or CH 2 Cl 2 S-, 20 R5 betyder hydrogen, fluor, chlor, brom eller methyl, og 6 R betyder hydrogen, fluor, chlor, brom, -alkyl, C^_^-alkoxy, trifluormethyl, nitro, CH^S-, eller CH^CI^S-, idet dog 5 3 6 7 a) når R er forskellig fra hydrogen, skal R , R og R hver 25 for sig være hydrogen, fluor, chlor, brom, methyl, eller 4 methoxy, og R skal være hydrogen, fluor, chlor, brom eller methyl, og når R betyder nævnte pyrimidinylgruppe, betyder X methyl eller C^^-alkoxv, og Z betyder methyl eller methoxy, eller når 30 R betyder nævnte triazinylgruppe, betyder X methyl eller C1_3~alkoxy, og Z betyder methoxy.R 5 represents hydrogen, fluoro, chloro, bromo or methyl, and 6 R means hydrogen, fluoro, chloro, bromo, alkyl, C 1-6 alkoxy, trifluoromethyl, nitro, CH 2 S-, or CH 2 Cl 2 S - except that (a) when R is different from hydrogen, R, R and R must each be hydrogen, fluorine, chlorine, bromine, methyl, or 4 methoxy and R must be hydrogen, fluorine, chlorine, bromine or methyl and when R is said pyrimidinyl group, X is methyl or C 1-4 alkoxy and Z is methyl or methoxy or when R is said triazinyl group, X is methyl or C1-3 alkoxy and Z is methoxy . 3. Forbindelse ifølge krav 1, kendetegnet ved, at 35 / r1 er A eiier As\ R8 ' R9 R10 149343 OCompound according to claim 1, characterized in that 35 / r 1 is A or As 1 / R 8 'R 9 R 10 149343 0 8. XO hvor R , R og R har de i krav 1 anførte betydninger, og når R betyder nævnte pyrimidinylgruppe, betyder Q svovl, X betyder methyl eller C^g-alkoxy, og g Z betyder methyl eller methoxv, eller når R betyder nævnte triazinvlgruppe, betyder Q svovl, X betyder methyl eller C^_g-alkoxy, og Z betyder methoxy.8. XO wherein R, R and R have the meanings set forth in claim 1 and when R is said pyrimidinyl group, Q is sulfur, X is methyl or C 1-6 alkoxy, and g Z is methyl or methoxy or when R is said triazine group, Q is sulfur, X is methyl or C 1-6 alkoxy, and Z is methoxy. 4. Forbindelse ifølge krav 1, kendetegnet véd, at den er a) N- [ (4-methoxy-6-methylpyrimidin-2-vl)aroinocarbonyl]-2--chlorbenzensulfonamid., b) N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,5-di-15 chlorbenzensulfonamid, c) N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2--methylbenzensulfonamid, d) N-[ (4,6- dimethylpyrimidin-2-yl)aminocarbonyl]-2-thio-phensulfonamid, 20 e) N-[{4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2--chlor-5-methoxybenzensulfonamid, f) N-[(4,6-dimethylpyrimidin-2-vl)aminocarbonyl]-2,6-di-chlorbenzensulfonamid, g) N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-benzensul- 25 fonamid, h) N-[(4-methoxy-6-methyl-l,3,5-triazin-2-yl}aminocarbonyl]--2-chlorbenzensulfonamid, i) N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]-2--chlorbenzensulfonamid, 30 j) N~[(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]-2,5--dimethoxybenzensulfonamid, · k) N-[(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl]-ben-zensulfonamid, l) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2- 35 -chlor-5-methoxybenzensulfonamid, m) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]--benzensulfonamid ellerA compound according to claim 1, characterized in that it is a) N - [(4-methoxy-6-methylpyrimidin-2-yl) aroinocarbonyl] -2-chlorobenzenesulfonamide., B) N - [(4,6- dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, c) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-methylbenzenesulfonamide, d) N- [( 4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-thiophenesulfonamide, e) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide, f) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2,6-dichlorobenzenesulfonamide, g) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -benzenesulfonamide , h) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl} aminocarbonyl] -2-chlorobenzenesulfonamide, i) N - [(4,6-dimethoxy-1,3) (5-Triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, N) [(4,6-Dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2,5- dimethoxybenzenesulfonamide, k) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -benzenesulfonamide, 1) N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) aminocarbonyl] -2- 35-chloro-5-methoxybenzenesulfonamide, m) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl ] - benzenesulfonamide or
DK153777A 1976-04-07 1977-04-06 SULPHONAMIDE DERIVATIVES, HERBICIDES AND PLANT GROWTH CONTROLLING AGENTS CONTAINING THESE AND PROCEDURES FOR COMBATING WEEDS AND REGULATING PLANT GROWTH DK149343C (en)

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