LU85175A1 - TRIAZINONE, METHOD FOR PRODUCING THESE COMPOUNDS AND THEIR CONTAINING MEANS WITH SELECTIVE HERBICIDAL ACTION - Google Patents

Description

.6- SCHERING AG

GmMtfeiîdwr Rechtsschutz 5 The invention relates to new triazinones, processes for the preparation of these compounds and compositions containing them with selective herbicidal activity.

> It is already known that 1,2, * t-triazin-5-one derivatives, 10 such as ^ -Amino-6-tert.butyl-4,5-dihydro-3 "f methylthio-1,2, ^ -triazin-5-one (BE-PS 69 70 83) can be used as an herbicide. However, these herbicides do not solve the problem of a good herbicidal action against the problem of weeds, while at the same time being well tolerated by several main agricultural crops.

The object of the present invention is to develop an agent which can be used against weeds 20 which are difficult to control in several main agricultural crops without their damage.

This object is achieved according to the invention by an agent which contains at least one triazinone of the general formula 25 as new active ingredients:>: CL · "30 I, 'R2 R5" MCH) "R3 1"; J 1 n R4 -7- \ 35 4-0 n

OS

en ß - Board: Or Herbert Asmis Or Chnsuan Brunn Hana-Jûrçen Hamann Posiansäinft: SCHERING AG - 0-1000 Berlin 65 «Poctfad) 650311 -e · jj \ Or. Heinz Hannae Kan Otto Mmeistenscneid 0r. Morst Witzei Postseiedc account: Berlin-West 1175-101, Santtettzeftl 10010010 / Chairman of the Supervisory Board 0r. Eduard v Scnwartzkoppen Berliner Commerzaank AG, Berlin. Kootottr. 108700800, BankietttaM 1004 'I v «itï Amt G.se.ismartflerim and Berokamen Beniner Oieconto-Bank AG. Berlin. Como no. 341750 ». Bamüeiteaftl WO 700 g Hana.lar.gisier AG Charionenourg 33 URB 2S3 a. AG came nflS 00β! ^ sa gc no

I I

SCHERING AG

“7- Gmwfbüdwr Radrisschuiz 5 contains, in the R ^ hydrogen, a C ^ -Cg-alkyl radical optionally substituted by halogen and / or cyano and / or hydroxy and / or C ^ -C ^ alkoxy, an optionally one or more times C 1 -C 6 -cycloalkyl radicals substituted by alkyl and / or halogen and / 10 or phenyl »fcin * C -C.alkoxycarbonylmethyl, one optionally ** or multiple times by C ^ -C ^ alkyl and / or halogen and / a or C ^ -C ^ alkoxy and / or the nitro group and / or the trifluoromethyl group substituted aromatic 15 or aromatic-aliphatic hydrocarbon radical or a heterocyclic hydrocarbon radical,

Rg is hydrogen, a C 1 -C 6 -alkyl which is optionally mono- or polysubstituted by halogen, C 1 -C 4 -alkoxy, cyano, C 1 -C 4 -alkylthio 20 and / or hydroxy,

Alkenyl, C ^ -Cg-alkynyl, C ^ -Cg-cycloalkyl or cycloalkenyl radical, a C ^ -Cg-alkyl radical optionally interrupted one or more times by oxygen, sulfur or nitrogen, a C ^ -C ^ alkoxycarbonyl- 25 C ^ -C ^ alkyl, an optionally mono- or polysubstituted by halogen C ^ -Cg-alkylsulfonyl group or an optionally mono- or polysubstituted, identically or differently, by C ^ -Cg-alkyl, halogen, "C - Cr-alkoxy, the nitro group and / or the trifluoro- 30 -------- methyl group substituted aromatic or aromatic - '- aliphatic hydrocarbon radical, R ^, R ^ and are the same or different and each have a

Iserstoff, one if necessary one or more times

Halogen-substituted alkyl group, an aryl radical I and n optionally substituted one or more times, identically or differently by j C1-Cg-alkyl, halogen, C 1 -C 4 -alkoxy, the nitro group and / or the trifluoromethyl group, and n are 0 or 1, and their Salts with inorganic I 2 / and organic acids. _g_! __ / 5 V___ Executive Board: Or. Harbart Asints Or. Christian Bruhn - Hana-Jürgen Hamann Poatansdirift: SCHERING AS - 0-1000 Berlin «S · Ponfadl 0flfl: * / 1 or. Heinz HannsKarl Otto MiMeistensOieid - Dr. Horst Witzai P «« si * e <* - Xen.o: B ^ ln-Wa * «75-101. ιβιββιβ; / · 2 Chairman of the Board: Or. Eduard V. Schwartzxoppen Bariinar CommarzbanKAG. Sarlin, account no. 10870 * 00. BanKMtzrtl 100400 I g Seat of Gasallsöiaft: Sariin and Bergkamen Beniner Disconto-Bank AG. Sartln. Account number. MI / SOOB. BantMaM 101700 α! 5 Commercial register: AG CharlottanOura 33 HflB 283 u. AG Kamen HRB0081 Bariinar Handa (s-G «s« lscnalt - Frankfurter Sank -, Berlin.

I u. Como no. 14-3S2. Saruuaitzani 100 302 00

SCHERING AG

Intellectual Property I) 5

Examples of inorganic and organic acids for the formation of the acid 10 addition salts are the halogen-I hydrochloric acid, such as, for example, hydrochloric acid and • the hydrobromic acid, furthermore phosphoric acid, sulfuric acid, in particular nitric acid, monofunctional and bifunctional carb on acids and hydroxycarboxylic acids, such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid, and sulfonic acids, such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid.

These acid addition salts can be obtained by the customary salt formation processes, for example by dissolving a compound of the formula I in a suitable solvent and adding the acid.

25 The compounds according to the invention are surprisingly extremely suitable for combating problem weeds with a tolerance, in particular for soybeans, potatoes, cotton, corn, wheat,

Barley and rice. Here they exceed the well-known 30 means. These properties combine great technical progress.

a

It is known that, for economic reasons, the most important agricultural crops are increasingly being put together in close rotation.

With regard to the weed flora, this means that more and more specific accompanying flora develop. If, including what is almost the norm,

Weeds are found that are difficult with the current state of the art in weed control I -9- /L.-- Voritind: Or. Herbert A> jn Or. Christian Bruhn Hana-Jürgen Hamm PamtaractoKt: SCHERING AQ. -------- r ~ rmiesill _,! tL NOr. M.ini Hannu - «.fl Otto Μιη.ι.ιβηκη.κΐ. 0r. Listen to WrCTnt Pn ". ", N. .. ..., - 1 m ... . , _ · F-r ^ tn-Wmf 117 ^ ifli, ritnfclaliTgftf iminm «_ Chairman of the Auf Jicmsrata; Dr. Edward v. Sctroarukoppen Barliner Commeazsank AG. Bartin. KomoJHr. tos 700800. BantdeKzWil 1 «400

E seat of the company: Berlin and Bergkamen Berliner Oiscnnio-Bank AG. 8 parts. Account number. 241 / iaoe, Banidattz * i (100 700 0C

o Commercial register: AG Chartottenourg 93 HR0 283 u. AG Kamen MRS 0081 8erlmer Handst * GeMiucnan - Frankfurter Senk -, Benin.

"· Account number. 14-302, Sanklaiizanl 10020200 sa gc no · «

SCHERING AG

_9_ GmMffalidMr Redrfaachutz 5 • i.

can be fought, conditions arise which easily lead to the dominance of such species.

One tries to counter the problem, for example, by trying to control it with full or even excessive amounts of herbicide. This often causes damage to the culture. Since the known herbicides can also have a residual effect on the subsequent crop via the soil, 15 damage is often caused to this. An advanced herbicide is therefore desired to have good activity against problem herbs while at the same time being well tolerated by several main crops which are in rotation.

20th

The compounds according to the invention meet these requirements and are distinguished by surprisingly good compatibility with the abovementioned cultures, and they can be used both in the pre-emergence process and in the post-emergence process.

The herbicidal effect extends against many weed species. Abutilon theophrastii, Ipomoea ssp., Solanum »" ssp., Viola ssp., Echinochloa crus galli, Setaria ssp.,

Digitaria ssp., Brassica-kaber, Cassia, Sesbania, Datura.

w

The application can be done by incorporation into the soil before the cultivated seeds or in the pre- or post-emergence.

35

The application rates for selective weed control are about 0.1 to 5 active ingredients / ha. In higher application rates, the compounds can also be used for total weed control.

ko -10- / 4 \ Board: Or. H.rtwrt Asm »· Dr. Christian Sruhn - Hans-Jürgen Hamann Poatanachnft: SCHERING AG · 0-100 Sattln as - Poaffadi «BtBTf i \ Dr. Heinz Hann *. · Kar. Otto MmaBt.naa.aid Or. Hora «Witz * Pomse-or-Konto: B« fin-W «« 75.1dl. 8 «* l * taftMeiC010

s Chairman of the Supervisory Board t Or. Sduard v. ScnwaruKOppen Berliner CommerZDanK AG. Berlin. Account mr. 108 7008 00. BamdertzsN 100 4X

g Seat of the Geseilsaiaft: Berlin and Bergxamen Beniner Oisconto-Bantc AG. Berlin. Account Air. 241/5008. 1007000 S Commercial register: AG Chartonenourg 93 HRB 233 u. AG Kamen HRB 0081 Berlin Handeis-Geeetlscnsft - frankfurter Sank ». Berlin, u. Account number. 14-382. Bamüeitzani 100 aas 00 saocir «• *

SCHERING AG

~ e * w «WicJ« * r RedrtudiuöE

5 Of the compounds according to the invention are notable for an optimal action of the type described, in particular those in which, in the general formula, IR ^ phenyl, 2-methylphenyl, 3-methylphenyl, k-methylphenyl, 2-chlorophenyl, 3 ~ chlorophenyl, * k -Chlorphenyl, 5 * 10 2,% -Dichlorphenyl, ^ i-fluorophenyl, 4-trifluoromethylphenyl, 2-thienyl, 2,5-dichloro-3-thienyl, xsopropyl, sec-butyl, tert-butyl, chloro-tert-butyl , 2-Hydroxy-1,1-dimethylethyl, - methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, cyclopropyl, cyclopentyl or cyclohexyl, R2 methyl, ethyl, propyl, 15 allyl or propargyl, R ^, R ^ and R_ are each hydrogen or methyl and n is 0 or 1.

The compounds according to the invention can be used either alone, in a mixture with one another or with other 20

Active ingredients are applied. If necessary, defoliation, plant protection or pesticides can be added depending on the desired purpose.

If the spectrum of activity is to be broadened, other biocides can also be added. For example, those herbicidally active mixture partners are those active ingredients which are currently used in Weed Abstracts, Vol.31, No.7 1982, under the title - "" List of common names and abbreviations employed for j "- in herbicides and plant growth regulators Weed Abstracts "are listed.

35 ko -11- *? / d »m« r - Board: Or. Hardert Asm · * - Or. Christian Brunn - Hans-Jürgen Hamann Poetanscftrift: SCHERING AS · 0-1000 Badin es. Pmfmrheaiil - *? Dr. Heinz HannsKarl Ono Mitteieienecneid Dr. Horst Witzet Posiseiadt-Konlo: Barlln-Wast 1175-101. BanfcWtaM 1001 «« - Chairman of the Academic Council: Dr. Edward ». Scnvrartzxopoen Berliner Commarzoank AG. Berlin. Account number. 108700 (00. Nuimj 100aao E Registered office: Company: Berlin and Sergkaman Beniner 0isconto-8ank AG, Benin. Xonto No. 241/3008, BanklattzaM 100 700 00 S Commercial register: AG Cftarionanourg 33 HRB 283 and AG Kamen hRB 0081 Beniner Hanoeta -Geaatlscnaft - Frankfurter Bank -. Benin, u, Komo-Nf. 14-382. Banni »tzaftl 100 202 00 jaocirtz»

-il- SCHERINGAG

G «w« ffalïdwr Legal protection 5 The active compounds according to the invention or a mixture thereof are useful in the form of. Preparations such as powders, scattering agents, granules, solutions, emulsions or suspensions with the addition of liquid and / or solid carriers or diluents and, if appropriate, wetting agents, adhesives, emulsifiers and / or dispersing agents, are used, preferably in the form of emulsion concentrates.

Suitable liquid carriers are, for example, water,. 15 aliphatic and aromatic hydrocarbons, such as

Example toluene, xylene, ketones, such as, for example, cyclohexa-non, isophorone, sulfonides, such as dimethyl sulfoxide, carboxamides, such as, for example, dimethylformamide, furthermore mineral oil fractions.

20 Mineral earths, for example bentonite, silica gel, talc, kaolin, attapulgite, limestone, silica and vegetable products, for example flours, are suitable as solid carriers.

Surface active substances are to be mentioned for the 25th

Example calcium lignin sulfonate, polyoxyethylene alkylphenol ether, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, and also substituted benzene sulfonic acids and their salts.

- 30

The proportion of the active ingredient (s) in Λ β in the various preparations can vary within wide limits. For example, the agents contain about 5 to 95 percent by weight of active ingredients, about 95 to 5 ″. 35

Weight percent liquid or solid carriers -12- - / Board · Or Herbert Asmis Or Christian Bruhn Hans-Jürgen Hamann Postal address: SCHERING AG · 0 * 1009 Berlin «S - PaMfadi - '? Qr, Heinz Mannse - Kan Otto Mittetstensoieid Or. Horst Witzet PostKJUMSC account: Bertin-Weet 1175.10t. BanUMtaM 10110010 -Z Chairman of the Auisicntsrats. Or. Eduard v Scnwamxoppen Berliner CommerzbanX AG. Berlin, Kooto no. lOdTOCSOO. BankMfttrtt 100-

I seat of the Gesallsenart · 3ertm and Bergxamen Beniner Oiscotito-eafllc AG. Berlin. KomoJfr. 24T / S0 *. BantdaitzaM MO 7S

S Commercial register: AG Cnariottenourg 93 HRB 283 u. AG Kamen HflB 008t Berliner Hanoeis-Gesellsdiaft - Frankfurter Bene -, Benin.

£ account no. i-t-382. Banktet txaftt 100 ZB 00 SO GC IV '-12-

SCHERING AG

Industrial property protection 5 and possibly up to 20 percent by weight of surface-active substances.

The agents can be applied in a customary manner, for example using water as a carrier in spray-brewing amounts of about 100 to 1000 liters / ha. The agents are used in the so-called low-volume and ultra-low-volume process is as possible as your n *

Application in the form of so-called microgranulesix. 9 15 The compounds of the general invention

Formula I can be prepared, for example, as described in claim 3.

The starting products for the preparation of the compounds according to the invention are known per se or can be prepared by processes known per se.

The reaction partners are implemented according to process variants a - d between 0 ° and 120 ° C, but generally between room temperature and the reflux temperature of the corresponding reaction mixture.

The reaction time is usually 1 to 72 hours.

. ? 0

The reactants are used in approximately equimolar amounts for the synthesis of the compounds according to the invention.

* s Suitable reaction media are solvents that are inert to the reactant. The choice of solvent or suspending agent depends on the use of the corresponding starting compounds and the

applied acid acceptors or bases. Examples of solvents or suspending agents are ethers such as diisopropyl ether, tetrahydrofuran and dioxane, aromatic hydrocarbons such as 2JO

Toluene and xylene, carbonitriles, such as aeetonitrile., 1 / 6- -13- 2 / Board: Or. Herbert Asmis · Dr. Christian Bruhn - Hans-Jürgen Hamann Postal address: SCHERING AGD-1000 Berlin 65Postbox 65 0311 Z 'Dr. Heinz Hannse - Karl Otto MittelstenscheidDr. Horst Witze) Postal check account: Berlin-West 1175-101, bank code 100 10010 5 Chairman of the Supervisory Board: Dr. Edward v. Schwartzkoppen Berlin Commerzbank AG. Berlin. Account number. 108 700600. Bank code 100 40000 3Roriin, mri Bemhm.n Berliner Oisconto-Bank AG. Berlin, account no. 241/5006, bank code 100 700 00 I "An mrr mei Berliner Handels-Gesellschaft-Frankfurter Bank -, Berlin,

SCHERINGAG

Legal protection • ·% $? Carboxylic acid amides such as dimethylformamide and alcohols such as methanol, ethanol, propanol, isopropanol and t-butanol.

Suitable acid acceptors are organic bases, such as, for example, triethylamine, Ν, Ν-dimethylaniline and pyridine bases or inorganic bases, such as oxides, *

Hydroxides and carbonates of alkaline earth and alkali metals.

s

Liquid bases such as pyridine »can be used simultaneously as 15 solvents.

The metal compounds which may be required for the synthesis of the compounds according to the invention in process variant a) can be prepared, for example, 2q by combining the compounds of the general formula II with metal compounds of the general formula

M - Z XI

optionally using a solvent 25, where M is a monovalent metal equivalent, preferably a sodium, potassium or lithium atom and Z = hydrogen, hydroxyl, lower alkyl,

Alkoxy or the amino group, preferably hydrogen, represents.

* - 30

The implementation of the metal-free connections of the general *? My formula II is optionally carried out in a two-phase system consisting of a triazinone of the general formula II, dissolved in an inert solvent, an alkali metal hydroxide, solid or as an aqueous solution, and a catalyst. Suitable catalysts are onium compounds, such as quaternary ammonium,

Ao

«? A

* / (J? Or. Herbert Asrms Or. Christian 3ruhn Hans-Jurgen Hamann postal address; SCHERING AG · 0 * 1000 Berlin 05 · FoarfeUl 00311 ** ~ f θΓ · He, nl Hahns · Kan Otto Mineistenscnetd 0r. Rtorst Witzei Postscn « * -Como: Berlin-West 1175 * 101 —Banx AG, Berlin, Konio No. 341 / SU, BeiUtMZMl 1® 70 -o Commercial Register: AG Chariottenourg 93 HAß 283 and AG Kamen HAB 0061 ®er ,, n ^ ~ Frankfurter Ban «-, Berta, ul Komo- No. 14 * 362.BenkleiCEanl 10030200

SO GC IV

SCHERINGAG

Gaw «rfa (ich« r Rechtsschutz * »5 phosphonium and arsonium compounds as well as sulfonium

Links.

Also suitable are polyglycol ethers, in particular cyclic ones, such as, for example, 18-crown-6, and tertiary amines, such as, for example, tributylamine.

"b! 10 *. The proportions of the reactants can be varied within wide limits. The reactions are preferably carried out with a 1 to 10-fold excess of R ^ - X and a 1 to 10-fold excess of hydroxide.

15 0.02 equivalents of the catalyst are sufficient.

The reaction takes place between 20 and 100 ° C, but generally between 20 and 60 ° C. The reaction time is 1 to 72 hours. Thorough mixing is required during the entire 2Q reaction time.

The compounds according to the invention produced by the abovementioned processes can be prepared by customary methods

Processes are isolated from the reaction mixture, for example by distilling off the solvent used at normal or reduced pressure or by precipitation with water.

If desired, by crystallization or column chromatography. _ The isomer mixtures are separated by matography as they usually arise after process variants a) and d).

The compounds according to the invention are generally colorless and odorless crystalline bodies which are heavy! are soluble in water and aliphatic hydrocarbons 35, moderately to well soluble in halogenated hydrocarbons, such as chloroform and ketones, such as acetone, carbon-15- ä / C_ «/ Board of Directors' Or. Herden Asm» Or Christian Sruhn Hans-Jürgen Hamann Postansairtft : SCHERING AG · 0 * 1009 Berlin OS · Ponrtaiit 0 (0311 'f Dr Heinz Hanns «Kan Otto Mitteistensaieid Or. Horst Witzoi Postsaioöt-Xonto: Berlin-West 1175-101, BenkleitaM 10010010 • S Chairman of the Aulstatt Council: Or Eduard v. Saiwartzkoppen Berliner CommarzDanK AG. Berlin. Account Mr. 100700000. SanUwtzaM 109 £ - seat of G.setiscnalt · Berlin and Bergttamen Berliner Oisconto-Bank AG. Berlin. Account Mr. 241> E0Ä. BwikJertzaM 109 79 a Commercial Register: AG Chariottenourg 93 HRB 2S3 and AG Kamen MBB 0061 Berliner HanWs-GeMilscmrt - Pranicrurlar Ban «-, Benin, i Konto-Air. 14-302. Bamdeitzanl 100 20200

SO GC IV

«T j i *

_15_ SCHERING AG

Commercial RecntxiOiutz! 5 acid amides, such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, carboxylic acid nitriles, such as acetonitrile, and lower alcohols, such as methanol and ethanol

J

Particularly suitable solvents for recrystallization are ethanol, isopropanol, diisopropyl ether, toluene, acetonitrile and ethyl acetate.

The following examples illustrate the preparation of the compounds according to the invention.

15

As 20 25 I-i6- 30 j '35 j ko y n I d »3 Λ! .. Board’0r. Heroen Asmi * Or Christian Brunn Hans-Jürgen Hamann Postal address: SCHEHING AG · 0-1000 BerHn es. Peetfadi 4S0T1 «~ *? 0r- η · ιηζ Hanns «<to Ono Mitteisienscneid Or. Horst Witz ·· Postsaiecx account: Barlin-W« at 1175-101. BanidettzaM 1001 * 10

à Chairman of the Supervisory Board: Or Eduard v ScnwartzxoDpen Barlinar ComtiMtzoanx AG. Berlin. Account mr. 1 * 70 * 00. SanXiaftzaM 100 J

I headquarters of Gesei.sa.art Beri.n and Sergxamen - j S Commercial Register AG Chariortenourg 33 HBB2S3u. AG Kamen HR8 0 * 1 maSSa ^ '’» oc r * * »

-16- SCHERINGAG

Commercial Rachtischuti? EXAMPLE 1 Λ ~ 3-tert-Butyl-8-propargyl-4,6,7, 8-tetrahydroimidazo

Ci, l-c7- / T, 2,47-triazin-4-one - »In a solution of 9J g CO, 05 mol) 3“ tert-butyl-4,6,7,8- S io tetrahydroimidazo- / 2, lc / - / l, 2,4 / -triazin-4-one in 150 ml of dimethylformamide, 1.5 g of 80% sodium hydride (0.05 mol) are introduced at room temperature with stirring. After 15 minutes, 5.95 S (0.05 mol) of propargyl bromide are added dropwise, the mixture is stirred at 25 to 30 ° C. for 1 hour and the reaction mixture is poured into 1 liter of ice water. The mixture is extracted twice with 150 ml of chloroform, dried over magnesium sulfate and concentrated to dryness. The residue is recrystallized from isopropyl ether.

- 20 Yield: 7.71 g = 66.5% of theory

Pp .: 89-90 ° C

Analysis: C H N

j calculated: 62.05 / 6 6.94 # 24.12 #! found: 62.15 # 6.88 # 24.27 # 25 30 «-17- 35 40

i A

* / Board: Or. Herbert Asrms Or Christian Bruhn Hans-Jürgen Hamann Postal address: SCHERING AG - 0-100) B # «1ln 46 * Poetfech 466311. Z Or. Heinz Hanns · Karl Otto Mmeistenscneid Or. Morst Witzei Postal check account; Ö «Hin-West 1175-101, Sanède« tt * nJ 10010010 Ϊ Chairman ses Au / siditsrits: Or. Eduard v. Scftwari2Koppen Commerz banx AG. Benin, account «No. IQSTQDBGQ. ΠιηίΐοίΓτίπΐ 100 «3 e M Mmm 8ertm * f Oisconto-βχηκ AG. BeHin. Account number. 241 / SOOL Bernde «tx» Ai 10078 J Hanamsrtqisttr: AG Chanonenourg M HflB 283 u. AG Kamen HPB0081 ^ • · s »* i

j SCHERING AG

! ~ 'Commercial Reducing Sifcc - EXAMPLE 2 * 8-Methyl-3- (3-methylphenyl) -4,6,7,8-tetrahydroimidazo / 2, l-c / - ^ L, 2,47-triazin-4-one

In a solution of 4.56 g (0.02 mol) of 3 “(3-methylphenyl) - ê * 0 4.6.7 18-tetrahydroimidazo / 2,1-c / - / 1,2,4 / -triazine -4-one; "in 60 ml of dimethylformamide, 0.6 g of 80% sodium hydride (0.02 mol) are introduced with stirring at room temperature"

After 15 minutes, 2.84 g (0.02 mol) of methyl iodide are added dropwise and the mixture is stirred for a further 10 hours at room temperature. The reaction mixture is then poured into 1 l of ice water, extracted twice with 150 ml of chloroform and the organic phase Dried over magnesium sulfate After the solvent has been removed, the residue is recrystallized from ethanol.

Yield: 1.24 g = 25.6% of theory

Pp-: 174-175 ° C

j Analysis: C H N

calculated: 64.44% 5.82% 23.13% ^ found: 64.09% 5.93% 22.90% * 30 5 35 -l8 ~ i - board: Or. Hardert Asmis Or Christian Brunn Hans-Jürgen Hamann Pastanadwift: SCHERING AGD * lflC0 Berlin aS - Pewtad, <9 0311 ..? Dr. Heinz Hannsa Kan Otto Mmeistenaoieid Or. Horst Witzei Postsöiadc account: Berlin-West 1175-101, BankMtzsM K »lt» 1d ± Chairman of the Aulsiöiisrais Cr. Edward v. Berlin-based Commerzoank Ass, Berlin, Konio-Nf. 109703800, SansfeiCuM 10040

Ξ Silz der Gesellschaft 'Berlin and Bergkamen Berliner Disconto-Bank AG. Berlin. XoflU> # <r. 241 ^ 008. Banki # <ash <103 7TBC

3 Commercial register AG Charioitenourg 93 ΗΗΘ 2B3 u. AG Kamen HRB 0061 Bertinar Handeis-Geseilsaiait - rrwlcturtw Bants -, Min,

; Konlo-Mr. 1J-3S2, Sanxiwtzanl idd 2CB0Q

SC3GCM4m m

SCHERING AG

-18- G «MiUkiwr KichtudHiti 5 'EXAMPLE 3 3-> iethoxycarbonylmethyl-4, 6,7» 3-tetrahydroimidazo- / 2,1-ç 7- / 1,2,4 / -1riazin-4-one i 39, 7½ g (0.28 mol) of dimethyl acetylenedicarboxylate are stirred 10 ", with 65.3 g (0.286 mol) of 2-hydrazino-inidazoline hydroiodide and 28.5 ml of triethylamine in 400 ml of methanol for 2k hours.

. The precipitate is filtered off with suction, washed with isopropyl ether and dried in vacuo.

15

Yield: 26.45 S =. ^ 5% of theory

Mp: 191-192 ° C (decomposition)

Analysis: Calculated C 45.71 / 4 Η 4.80 54 N 26.66 54

Found C 45.53 S H 4.8l 54 N 26.53 H

20 ″ 25 l -19- 30 35, ΐο // I / ^ N.

! > Board: Or. Herbert Asmis Dr. Christian Sruhn - Hans-Jürgen Hamann Postansdinft: SCHERINQ ASD-tOOO Bartin 46Poedaiii 4SI11 i Or. Heim Hanns #Karl Otto MitlelstenscneidDr. Horst Witzel Postsdiedt account: Bertln-Wee "TI75-W1, SentdartrsN WB we" · '- Chairman of the Supervisory Board: Or. Eduard v. Schwartzkoppen Bartliw CommerzbanK Aß. Berlin, account Mr. I0S 7008 00. OmtfMoM Ί444ΒΒ44 I Company headquarters: Berlin and Sergkaman 5 * f! Ln * f P * lc? L? 0 ^, nlf.Ae · ****** 5 H «nd # lsr« gistef: Aß Charlottanpurg 33 HHB283 u. Aß Kamen HRß 0081 f · * 11 "*?) Γ> ,, 11 * rnsn - IBaak -, BardK, i £ Account Hr. 14-383, BankJert2a <W 1092000 saecnr- * · M · *» ·

SCHERING AG

_ 19 ~ e **** b8di * r Legal protection 5 EXAMPLE 4 3-Ethyl-3-plienvl-4,6,7,8-tetrahydroiraidazo- / 2, l-c7- / l »2,47-triazin-4 -on i0 To a solution of 24.46 g (0.096 mol) of 3-ethyl-2-hydrazino- “imidazoline hydroiodide and 17.8 g (0.1 mol) of ethyl phenylglyoxylate in 150 ml of ethanol are added dropwise 50 ml of a two molar NaOEt solution and heated under reflux for 10 hours. The alcohol is distilled off, the residue is mixed with 150 ^ ml of H ^ O, extracted twice with 150 ml of CHCl ^ and the organic phase dried over MgSO ^. After the solvent has been removed, the product is recrystallized from isopropanol.

20th

Yield: 3 S = 13 96 of theory

Pp .: 151-152 ° C

Analysis: Calculated C 64.44% H 5.82 * N 23.13 *

Found C 64.10% H 5.97% N 23.11% 25 '* 30'> 35

• L

4o \ md · v tn J- Board: Or. Harbart Asm »· Or. Christian Bruftn - Hans-Jürgan Hamann Postal address drift: SCHERING AG - D.10Q0 Barffa, tS · Aoadadtamtl Z Or. Heinz Hannia K„ l Otto Mitteistanseiatd Or. Horst Witzal Pemsdtadc account: Bariin-Waat 1175-WI. 'KjaT »* - _ï Chairman of the supervisor»: Or. Eduard v. Satwenzfcogpeft 8erfine <CoflimerztMnlcAâ. telbÎ account-Mr.iai7aoi <n, 3aMlatayri'Mi4Mai | Company headquarters: Berlin and Bergkainefl Berliner OUconto ^ eank AG, Berttn. Korrtü-Wr.241Λ0ΕΜ. BencieCzaM ΙβΤΜΟΙ 5 Commercial Register: AG Chsrlottenburq 93 HflS 283 u. AG Kernnen HRB 0061 Sefllner - Frmfranm Ban * -, fier * ·, il * * account. 14- "ButiecMUBas00" <3Cir "i i.

[i.

SCHERING AG

Commercial legal protection • EXAMPLE 5 5 - - 1.22 g (0.01 mol) of methyl dithiocarbazate are mixed with 1.78 g (0.01 mol) of phenylglyoxylate and - then 5 ml of ethylenediamine are added

Heated to boiling for minutes, mixed with 50 ml of HgO 10 after cooling and extracted with CHCl ^. The organic phase is dried over MgSO 4 and the crude product thus obtained is recrystallized from EtOH.

| Yield: 0.47 g * 22% of theory

15 p .: 2l8-219 ° C

Analysis: Calculated C 61.67% H 4.71% N 26.16%

Found C 6l, 60% H 4.99% N 26.4l% 20

The compounds listed in the following table can be prepared in an analogous manner using appropriate starting products.

* * 30 35 -21- ", -

Ol.

I cn · ^ · j 2 Board: Or. Herbert Asm »· Or. Christian Brunn · Hans-Jürgen Hamann Postal address: SCHERING AG - D-i Berlin es · Postfach 65 0311]? 0r. Heini Hannse * Karl Otto Mittelstenscheid · Or. Horst Witzal Postal check account: Berlin-West 1175 * 101, bank code 10010010 j * Chairman of the Supervisory Board: Or. Eduard v. Scnwanzkoppen Berliner Commerzoank AG, Berlin, account no. 108 700 600. 3 «nKiettzahf i00 <oöoc! I am the Gasallschatt: Berlin and Bergicamen Berliner 0lsconto-3anlt AG. Berlin. Account number. 241/5008. BanUeitzani 100 700 00

. _21_ SCHERINGAG

Intellectual Property Rights n 4 -. o o w ° o w w υ υ oooo ^ o '.- n. 03 CM ° _ 5 y; O O oooo i ιο «λ, rtuvaco c-λ ce c \ cr. M σ> ιΜ -τ

lUm ol ΙΛ ΙΛ CM H Q CM CM

* -HO i— (i — i CM H CM i “l CM

H + l / \

OC

, ¾ oj .. ·· .. .. .. - .. ·· ·· - · Ή 43 · · «· · ♦« ·· * »οοα ο. α α c. α c. - ß · β. ß <>> C Ce. b. CE.Ct.Cc.CE.Cs.fe.lfct «· Λ Ο C, Μ '15 ^ Π» | ό I I I H | * Ν Η Η I Ο Ο «ej -" I Ο - $} Ό W Ιοί. ο Ν -β -I «ν4, Η 1«> * ε - 'οι I I ο Λ ο Ό £ Ή 1HL «

0 0 S ^ U-rieO >> JH

/ SN «-Ρ -α ε U tt ιΝ. “, Β <β ν S pi fi -Ρ · ® 01

Ό Ό -η -Η £ Ο® I

__ · Ρ Ή s ο «i. +> Λ Η I

20 εε -η w t, -β ι «. - g fi · Η C "C -P> ι CO U ΙΟΙ Ν Ο 0 C. ^ ejC '+' Sl« U U "fl £ +>. fl Γ '* ® · “ο · σ>» «ici. - +1 ο · *> »> 1 £ C. CO Ο -Ρ νΟ · I Ν ε £ £« +> -I® - S CO Ο -Η 4 β U ® .— +> Ο Ό Ο

U 5. + ι + 1-11 lit "· -Η U

P -Ρ φ I \ 0 3 Ο Η -4 * - Ε ”Ρ yj ® Φ + ι cC - · Ρ -> ι ι νΌ -Η? Ι„ c ** * ι.- ·· β · «Γ- 03-0 £ 25 3 1 JL ce c rc ifl - co -p -ccua

<3 S0 ~ -0 -O -H-isOO'HN 10 Ό P

C - ’(" · I νΟ I> n U - | H fl rP I>. -P

m P- p- - _r c-p -r -s * 3 -p> · -s * £ ®

YY - - VO | -Γ I «îs. I I «t. W) l <e -P

S. vO '-O - £ I C Æ · ί · | p-i £ H -P U C U · φ - · -. T4 ri fl a - ÏS Ή r *> f "* fl-P P ^ *;> -3 * = -3 · S IN>» N icM-PNJi-iriO.NO "£ '

10 10-.fl yjflcn-3fl +> - 0®P t "· O

»„ U ri l H -P Je -rt I H | Λ -P ® CM il · Ρ I * L

* O> «- *> 1»>, U fll.HV.llUS.-O.i.CO \ Û if * 3 οι et c P o, p> »ïn. p -p i t | i -p - - «30 ® 3 ® 3 ® -'s. o S ü | l. \ £ 0 W e N N - 0 ® £ fi £ fi _ £ L — l L 0 1 Φ «yl I 0 * I -ri -« * Ί

B S. N C. N Û.- 0.-5 "| - | P-H | H-VOC <HN

fl I fl rp fl ri fl 1 CM ri - I (J> 1 H> * CM * 0? "> ® <z P 'ti>» Ti> »- CO - 3 ICM. - -P - -P» - 4 * I ijT1 · i. -0 ti £, η I, ri ai s, l I Μ o | CM 3 IH l -JT 3 h rp -P -PP il \ | H \ l -H 1 P \ | Λ N Λ '' «JH 1 ca + *.> · = * = · -R S ül 'fi o» £ N £ O * f N -p Oi C \ * * - * Ί i. P - 1 ii .oiPflPjtifliiloN »- ··« OJ C ^ CM -Jr- £ H ® ”C ®, -i ® * 3 ® H .ce φ C« „Σ - W- ^ rr (£ -Z-TiZ - +> fi -Ρ -0.-Ρ 1 ri I i Ici i Ici, i Ξ * iox »S '1 ^ 1 JL ^ Λ se v, \ <c- vJ c- \ \ 1 r: -pc \ J ^ p« SJ c -. p es n <i — io

H

C.

«O cm ci -a · in PVOIV. acvrlT-lTtTPr-tT- ® ^ tO Œ f -22- jfe Board of Directors * Or Herbert Asmis Or Christian Brunn - rians-jurgen Hamann Postal address: SCHERING AG * 0-1003 Berlin β - rraffüti 050311 - ~ // * ->. Or-Heinz Hïnns · Kari Otto MmelstensawiS Or. Horst W.uii? O «« n * ot-Konio: S.rHn-W «M17S.« ». BuikMtzaW 1601091 «'\ Chairman of the Aulsicmsratsr Or. Eduard v. Soiwarukoppen Senmar Commerzoank AG. Berlin, Cont ^^ r. 1 »700000. BenkMtzaM 100

Ê Sin der G «rope» cnaft: Benin «na 3erg * amen 3« · ιιη «· Oi« onio-3ank AG. B ^ ln. Konio- + r. 2 »l / snt BarKMtcaM ICO 7C

g S „d« UfM * siar · AG Cnarlonen0ur5 93 H8B2Î3u. AG Kamen HBB0061 Seri.ner Handaia - ^. Aeliacnan —PrwMurtar Sana -, Sedin,

o nana ice regiaier. ^ »<Cmo no. ΐ - * - 3βΖ. SankieiczaM lOQStSOQ

«* * I ·

.22. SCHERING AG

Commercial legal protection 5

N

y ουυυοοοο

oOOOOOOOO - CMCOMinVOHOCOOO

.. ® a, cs v \ co tn o - ~ «h w w h w w h

io 2 A

* («·· ·· * · * 4 · tl« · · ΗΦ # · · · · · ·

Zi ΐ & ρ, ααι =. & Ρ, αο-ί

® g 6. &. Cb <*. Cb Cb Cb Cb.'O

H +> * na >> c. · Jc o Γχ S 1 cu * ι jx. «2 or

0 1 o! I 1 <e M. , X

4β fc I Η Ο 3 β 1 Oi t -Π H ”N-WO | '0 1

> »- IW,. Λ E H; h S O

£ (CM, NJ 3 Η E ·, - β I S

d Xl «Η 0 H. ! w. * β K «

fc! OgfcOXH-S'O

+ i0 N H 3 fc | g t Ή

® S β 0 ϊ * ι 3 Ο Η Ο E

Η d 3 fc £> ι 0 O fc H

, 3 Ή 3 «JS. H L. 13 O

co H S. > »Fc d 3 3 ->» · fc - s -π æ *> fc: · * * Äs-e on p- η 0 ® ® + »iE ä β o>.

* W -.0 fc fc + »« H d fclX

vnfifc 3 + »1 +> fc fc 4J Jf · β - Ο 3 >>« <3 I>, H «I fc .a · ι>» x: +> * co o. «-wc + j 1 _s < £ d IP «· - | JA IH <0 hi® fc «0 - p» 2 i fl \ S + ji fc +> - 'Λ - -s «co -di £ HH ® P- - \ 0 I - CO H CO ·« s® + * * *? 1 - »Ο Γ ^ · - fc - c £ β +> I SO C I 0 -3 * C fc -CP - WP-0

M ft Η I SO -0-0103 OO - jX - I

25 SI fc so - -β * I η I Η I>, - ι so -s * j so -a «'S rs +» - X ι -a ·> s -s · ~ -r -s * ι - - i 3 I | \ N - Η ISICI d II H 9 · ί sc Hat - ό >> c ®c «ej,. h s - ι h

• rl - SO · - «ß * rl H H J3 H + J C> 1 H 0 (H H S

Λ -’CM »C-TCtüM £ NC.N®0OS®'Nj >> d

fc ή - -er o io -Cd -P «I β Η I Φ« i +> -H

Φ fc, | H II— I ft -H IHnHl-r-SHft'clSfc

> H \ | H J rt c I fc ^ fc 1 fc Os | ftfc II XS H

->, 1> ι I H +> 1 -U H + J - £ | + JC- \ H II

, fc αι οι 00 cc I fs fc Γχ> i iX co h η fx ι, - hx 'ο hi ο -π «η - -ai o j- jr, - s ι ·« ·> - | w, fc - a * 1 20 Ό S, H-ft ^ -Ot3H-H - +> - p-dH-HXj «- jg - ft d fta ^ oi iw« ci - n >> cj> »i +>« o hIWiI -h fc · «Co-6-sofc - - co ι-

Ε J \ l n fc 0 fc lH, i l -u * 1 rt ® C C \ JH

d pi \ ** 3 +> +>> * ’a Si x h ι« Si · μ η i XI

2 fc 0 fc (S -fc (X 3 jX I | \ O, \ i> », x S, X 3 3 <fc iX

0 M> 1 ~ l h CI a * 01 ΙΛ 0 | £ 0 | ’3 le, C Oi Q -H> 1 0 (

H ® «fc - I - I 1 - l +» l «-dl 1 Ξ H I

£ V HW -d-w WH WH 0 H - Cl> »H WH HH

35

H

d

H

mso p-co os C T- OJ co-s · ir \ ^ r- fc rl HWWWWW 01 «® ko 33 tTi f -23- / IV — O / orsiand: Or. Hirbtn Asmn Or .Christian Sru / m Hans- Jûrgen Ham * nn »asunsdinft: SCMEBING AG - 0-IOOB Bartln« S-Po «fadi4Sd311 • - / \ s XH« "* Hânnse · Karl 0« o Milteial.nsoia.d Or. Horst W.tt.1 Posucnwp- Korao: B.rliHIV «t 1175.« «. BanklaftzaM 1010010 / X Vontttcnder cas Autsicnnrats: Or. Eduard v.Sdlwartzxeecan Sarlmar CommarzaanK AG. Berlin, KontoHr,« a 7nw00, BanidwtaM 1C0

l I seat dar-Gasellscnaft: Bariin and EcrgKaman Sarlinar Oiacomo-San «AG. Berlin. Account Mr.aWiSont. BankHlxaol «B7C

> 5 Commercial register * AG CiiartottenDuro 93 HflB 293 u. AG Kaman hRB 0001 Berliner Hanaeis-GesUsaieTt - Franklurtar Bamc -. Barttn, lu. Account number. 14-382. Banx routing guide PBββ PB Cd * *

. -23- SCHERINGAG

Commercial «· Legal protection ΐ - U ü 0 0

egg O

υυ ^ οοοου- «· ο ο <ΟΟΟβΟ · 3 ® ίΐΛ <HrH IT \ M ir \ VOC0 '- oio c> r ~ r- c \ r- c- \ rv

10¾ ^ H P P P P P HH

»" * H Φ ** * · * · * · e · · «e« ·· H 4 ^ * · - · · · · «· · 2 £ t, * · p- p-ft c. Cs. Ft uh * ft ft ft fr. 6. fr.fr. ft: θ * «« •> c

• CO II

ft Χί l | i 0 Ή

I 0 O P U E

, 15 O U N g TJ P

’15’ U Ό «S P *? JL <· * ® * -α ΟΛ s ·

JjS o S JC p u «ft IC

flwr u j: "SO u i—" o

<Ό «U -h>, P S CO I

A 0 S U P O £ Ο -ί * 'P P1 2 3 4

"U, C P O U" S P I P "· I

U * 0 «® · .μ Ό Sh I 0 - C

P> * Li +> | >, +> CO Li vO P

• - Je · p I eo jj · β · TS - N

p ec «cO - <a p P suit>> -C« 20 <* Sh 0 P »Sh I * · £“ T1 ώ - θ 'C P 1 I p · - + »CO voce 1-t Sh

- 0 «<3 * CO ·> <so · O» Ol «I P

«2 | -PI - CvOC -CP p »· -3 * I P -» I

- -s · icso -o ^ oi -C ici · «H \ C · * I« v ρ * I -S "I | I CO vO OPIP · S ΡΠ -C - N VO -3 * I -3> H -3 “· -1> 1 C IC 0 VC P CO 0 - IP | >> l P» £ · -5Γ CP QV O «01 IN -P-TC SC hoc - · | I« N - I ~ S - PO t> Sh IP MP ShPVOC ^ C £ «oa>« k

M> ip - P P N U N es «0 HP ftp - I. * ''» J

C c. Sh · vo |> x>, 10 de ß, «.3 · l>% N llnP-C O jS.

2 * 5 3 «P I Cl £ -ri ftp OP I -3 * e 0 f'v p - p p w J Ό -C I« - »- PU 0 Sh U U P! ®P ΙΙΌΝ Ul £ ft S, p cm (U-P UP ftp>, c £ U p IS i «pp

• rf l'5 ’! > v * =, S ft iS I | \ £ P ftp>, b | HP ΙΟ ^ GIP, I -3 * 1 i -sn cc -3 * 1 p N π t - ->. U OV (OL

U I0J i \ O - C · I - ««>, fv P 01 £ p - SJ

«« - ft | N. I CM I (Μ λ «g P £« TI «, - P jN, O 0> H! P 0 01 - H - HUP - · E | P |« -3 * 1 - ** 's! UIH | PP | P Ip>, P «01 H" S g - Ο β UH iS ftP> 1 'S.' ►. Sl C * nJ CI £, - s | S IOlw-β

. , 0 H * oi, - c iS C | S «| \ 0 N I U C Ol σν - I P

“V Οι μ In. * oi ii ü | £ ul yes n n ο i i | H, - · E

30 <P> - si J3 I * Ä I ft l U ft, IN. £ 1 P PSJPP

«R1 ll ftp ftP Η Η OW I Ul 1 | ·> 1 l \ w I

£ * ici. <J \ 0 U - U ->, - «- <« - 1 I «CM. P 1 U | CO O

«- si i C a lil, 0 I«, £ I «. >, H, i P 0 Sj 3 I I U

2 + J »pp 3Sl 3 Si P sj XSjp | - ÖP H" ® «0 ^ -o PO HO« 0 0 iS> »Nl XO I, -> *? SN CP ftN ft N 2N iw £ N ON Pl” | 10 «£ 10 10 (OPI PI h20 Sh S>« «

OSO ΛΡ- ^ Ό ^ Ό c-1-Π OH oO P ΐ OO .CU

P ft U * P w Ή P S - S N ι · <ΐ P P C ft P

4 '<E l> 1 i £ i s I s t | CM, I 0 i £ i p I «

- ^ CCPiPfttP.HO'HHCPpP’sJcOOCOPt-StJO ^ P

H

<D

P

ft ffl'i, ^ ocvopci ^ -a * in

p '•' fl'JoicMc-icnrvcAeAiA

o. 'to = 2k

- ^ Board of Directors' Or. H «fb * rt Asmij Or Chnxtian Brunn Hans-Jürgen Hamann Poatansdinft: SCHGRIHG Aö · 0-1003 Berlin OS - PgetWOi aSQSII

2 - - / t Or. HoinzHinnot · Kan Otto Mmeiii.nsen.id Or. Horst wnzai Peaaeimsc-Kenio: Berlin-w ^ «ts-iw. B «fc« tahi loswew 3 • Λ Chairman Ces Autsicmsrsis Or sduard v. Saiw «nzKooo« n S «f <m« r Comnwrz & ank ag. Benin. Account number, ΚΜ7θαβαο. BankiMtzaM ic 4 | Registered office: GHsallscnaft · Benin una Bergsamen 5, Commercial Register: AG Cîiarïonenourg 33 MRB 2B3 u, AG Kam * n HRB C061 <omo- «r. ι * -3β2. Bemueittam tcoazzoa ‘„ ·

-24- SCHERINGAG

G * w «rfalidi * f Radriudiufac 5 υ o. υ o 0 0 0 0 Τ 'ΙΛ CM [V.

(J 9 π νΰ (fl η «-i υ ο υ μ cm

ο «ι ο ο ο II

«.Τ ο -c t '' - σ \ s Ο ιη. £ <fl <Μ «λ ςο \ 0 ΕΛ

-, Λ Ο Η Η <"<CM CM Τ 'CM CM

(Ο c τΙ ® ~ - Η · + * · · * · · · · · «c a a a a a a p, a .y a a a a s * ùu ü. Et. Ce.

• ri -U

r 01 «

m II

: o «» r- *. o a ^ ι ι ο ι ix oi u CO S * <fS Ol I I fl ΐς -. Ό ÜI ι fs T- >>

* · 'Rs.ci> »? ι τ 'οι - A

-00 Λ &. fi -, ICM «\ 0 I U« O - ICM T * \ 1 fi, - 9 Ά UIkm Si - l ** 9 I N -W -S * 'S! "ICM O * IC £" il O VI H + "h -ha · +> a ο K ι α i *>, NS" CI 'JN a O fl "ο β ca +> o cn M e -a tj τΐ -o ο · Η ® «- <fl T» ta s I * »! i. -μ -T CO -W -rt E fl · -H · 9 nn H - * -> 1 I * * <£ tI tI 0 VOt αυ ps σ \ c N · * ^ τι o S ι * -β «ls * | - -H - I o fi, Tl fl C τ |

- CC N Ό rs fi, fl o>, I N

«- a ι fl ►> fi, ä M * - ι - n ~ A fl a>, -ri

S h-U-ICJÄ «N U ü U

«'S) O *>>, - β fil Λ -U · - ** g jS ι fs = ir * L u« «.Ci bo i,' m λ i? I ή s u« u +> a n.

C 0l ^ -ai «-μ -μ ι I -3" I

3 T ^> i (Μ O fS -W · |, «· CO · P * l * oc fl h - c» u .οι ι s coa +> a -c ι «

C (a ', CM, Tl H, ai. "0-0 10 S O H

• ri .rt -s) a sj I v <- I NI CO I “I> * l · *“ Λ u ο os cm - r- -c * »-e *« -co J · A "si fii VN fi * Wl wl ° * · * I 'SI NI - I + »l«, «s α ι ι * si ve e -s .s · -ce« N.

> COfl I H σν I »-H 9 Μ \ ΟτΙ I -ri 3 O

i.iHCM ”I O * CN I S. »N V—» H I I

ι «_ s w | cj, -i fi ι a h a 'j · a h a fl 9>. Tl I 'S * >> Γ * Ή ^> Ή ΙτΙ> »τ | N * · fl +? C CN C -P fl * fi, XI- H li 0 fi-wtd • * -U I 0 2 tI a -P «-P>, -p« + J O 'S ·

in «£ c H p a 3 Ol A I -P I Tl I I I

-J'JS T>, s fl> fl fi \ ors ars £ is ο oa -iaa -n -p ι- a -ci ^ -et a 91 e- · -ei an 2 us ® sux ο - ο - ο · Ι - «a - a fi, .0 · <- *« a «cm N cm ww wcm >> fl p« a ι, ni h. u h - - ofl

1 o 1>, 1 A * in 1 | t <1 tn 1 ι-n l S

A -p a ^ 9 <ns.i a m en si η \ ι β ή 35

H

«

•H

S- OS ce o \ O T- CM <T \ ^ ^ -m "-c * -S * Φ 40 -« / -25- o / m / / L ^, - understand: Or Herüer »Asmis Or Christian Sruhn Mans-Jürgen Himinrt Poatansehrilt: SCHEHINQ Afl · 0-100S β «11π« - Posttech «S« il · / f Or. H..nï H «nns. K« n Olto MiB «lsten * a>« id Or. Horst Wnz.l PoaueieacJConto: Bwlin-W «t 1175-101. BwktotaM 10010910 I Λ, chairman of the supervisory board: Or eduard v ScnwartZKOPptn 9« riin «r CommerzoanK A (3, denin, account number, ιΟβ 7009 CQ. BanUeeCCaM 103 «| Siu dar Gasaüsmaft: Sarnn and B * rgt <am ^ n SarJmar Oocomo-B« / »AG. 3artm. Kontore. 241 / ax *. 8« nfcJ «* aaM 109 ni o Haoeeisregisiar AG Charioitanourc 93 mRB 283 u. AG Kamen MRB 0081 Sarlmer HandelsSaiHadaft - Framefurter Banfe -. Berlin, u.Konio-Nr. 1A * 3 £ 2.Banxianzsnl iûQ2Q2Cx) 5

_ 25- Commercial · * RachbschutK

• ►

SCHERING AG

· * Ιυ o «oo y ir \ -c- C co <-« ^ υ υ ο ο o

m Λ 'Ο Ο O Q O

• IQ η 0, £ · * η 01 «Λ λ so iVJ fi = 3 SC -r <« τ r- co m Ο Ό T “* T-ι t- <r- * ^ ·· · * ·· · ······· “** 'V · · · · · · * 4 £ c. o. c.c.aa, ûft r (0 ö 1S ü 15 π • 1 £ * · i

£ o 0 I

** S like this

H I «iS

I fl 0 fl 0 0 I

O -H N -H S fl -O

2 ε «a« J Η I S

β -rl * 0 H fl S 0 «I». _ _ fl l * -H O H H S fl 20 * * S s la S 0 «y

Sft-yfl-ytiflH

a - £ 2 »g? «G * 0 3 W AUS £ o l ·. -a * * o «fl .e -y 2, fl ι>» la> »« <0 fl £> 0 Λ + »Λ V, U>» £ u β β ο -y -a τ «* fl U * U 9 >> * u> »-y ι yyj * · • y Λ« cû 0 ι «-yoa -y - -y co î,« 125 5 * * r »i - yyi · -y · ·» » co «rv- * o« ii * · co c ® c - c soc * c * syc σ * c

β - 0 +> 0 COO -ONOVOOlO-O

3 NI il * l «3 · I“ I - ι co ι 03 ι fl - -3 * J | 3 N -S * I J * sO -3 «-C -C. -e <m ^

S SOI »I - I H I * I I I N I N I

-C cas OC NC- ^ SHS-C-S

o -s * · η «ή ι -y w y ι -y> n -w so -y so -y J» IS NS HS ImS HS MS - N IS

• Ηβ »«> t β ««> s «îh« ^ * OH «-3Q> - ►> H son oy.Q, y.CH« H | .y> ,. y * f -> u. Λ UIUHU OU y ^ ftlsHfcyJe i «yy hy« y! * Y ® y oy>, y cy • ® | ->, I Si ai S ι h ι y I, β l fl EN "N lis, Ifs, IN G , NJ \ I fs t -s * I «-3 * 1 os -3 * 1 CO -CM co -3 * 1 I -5 * IO -SM H -3 * 1 • co * · Ο ι» ι - ι - co - o - U *

9 ICI ί, Ol H CM H Ci HCl I CM «CM« CM

<H · i ·>, * · >> - >> "H'-y-y.

Ä> s Its <Ί 1 * 1 X | τ * X i * · * X y> 1 y ι μ I il *

a Ni I NI «NI« NI ® NI 0. Ni Λ ni NI

01 Hl £ l £ | Λ I Ο I II II.

: I __ J * fs * S IN ON ON ONmNHNHN

35 a Ol O Ol H Ol H Ol H 01 C. Ol> s oi> * 01 01 yi ΟΙ ΟΙ ΟΙΟΙΗΙΗΙ BT ® CM>, Cl>, cl JyyeiTHyHy h - 2 «o * y-ü-H ** <- . <.

I ICM I II * «| lr + i! CM I ICM> | C4 1 IC4 ^ \ l ^ Μ Λ Μ «Λ Μ ^ M \ l œ M o \ \ | a ι.Λ .3 -3 * in so NcccsOti -sc * -c - = * -o * in m

-H

I / -26- I '"' Hprsland: Or. Herbert Aemis - Or. Christian Snihn · Hans-Jürgen Hamann Post-soul: SCHEHING Αβ 0-1000 Sariin OS · Poadadi« S0311 I - * * ΟΚ, Ηβιπζ Hanns · · Karl Otto MittsistenscneidOr. Horst Witze) Postseieoc account: Berlin-West 1175-101, BankMtzaM 10010010

| .2 Chairman of the Supervisory Board: Dr. Edward v. Schwamhoppen Serilrw Cotnmerzsank AS. Berlin, account no. 108700800. Banidactzaftl KB40C

I Headquarters in Gasallsetaft: Berlin and Bergkamen ^ 7:00 am I Commercial register: AG Cherlenenburg * 3 HHB 283 u. AG Kamen HR0 00 * 1 ^ t ^ r? Î23e ^ a! N * ï! ^ Irt lŒJKOJ ^ '• HW · Τ Λ 4 «

SCHERING AG

GMMfbiichwr Reditttchoti 5

U O

0 0 '= a in τί t va ο y o

so O «« y o OSO O

® ο o i ίο ο ο ζ in approx. + »R». -s * c- \ ο η- o vot * p-i5s - · <n «m vo ovo mco-Ητ- · n R t * * - τι τη τη oj r * ^ 10 gn« B ·· · * · · «· ·· .. U. «.

• · · · ♦ «4> η ß.

'® ft ft a o. A c. an * t, -R ta. X fc «Cs» 6s, ft ft τ '«

H

H

0 Λ 15 «X ι · 1 Λ Ο ο type, - u βΐι Ό ι« β S ί * J X Ο • Η * ί ^ fN. JZ Η S Η -μ I -4M IQ 9 Η I ® ® Ο - Γ'ν U Ό Ο Ο Η -μ Ν Μ οι -μ Η Η Μ '1 «- I« a ΟΛ Ο ecOcOOlTH ^ t * »^ χ · β - Ην »| -, 0 £ · £ t'- r- Ε ι ιμ« ο u β Η ·· "· -ri fs, ν, ι - * ο * W, -r (VOavOCOOIItv. ^ , • P Ο "Ο» qu I ο »Λ Ο U -d * I 4 * 1 * β * τ ΰ Ο

4 »Τ3 I -θ '1-0“ X «* 0 -, L

ι X η ι Η ι Λ ica X * 4 «g +>« Ο Λ X C X C β \ ι ί ^ I ο * »β £ Η bO Η U I ef * Hl -μ

I «| s Η -ΜΝΙ, Ν-w Ο U £ X -4 * I

, ς β * 4 * £ «« «® Μ +» -rc ι ® 3 vô β S Ή ft ή * »β ®“ 50Π · υ - + * ιν * often ι · π + »y χ η rs β« 3 * · '-'Η U + * 00 Η I 5 Η Ν - ·.

τ * ι «® · -π ι a ι - · ε ο 2, 3 β νο c: Λ Η C - C ^ N I r \ N C Η -5» «Η - Ο.

W ShOr'-OCC-SMCO-aM-OO {s Ç Η U -4 · I

• £ ι -1 1 * · I - νο I U -Η χ -μ ι 4 * '>. Η -3 * Ό -3 * ^ - »CJ / -» Μ --4 ** 0 VO’S.jSl Hl '· ΦΙ - I Η * Η «-3 * I X. ? 1) \ Xd U Ε R -3 * R X ΙΗ X ΙΗ ι d £ -4 «{* · φ 4 * 1 C Η.

· Η Η I Η C ν, Ι fi V.I Η Η β 1, s - β H

"^ 30 TJ -ΟΝΗΝ®! «I X N U Η ^ U Μ £« * t «X« Hrs.HfS »WflH X S 0 - ft Η

"® H S Η £ ΟΙ £ Ol U Η" ÄTH | r * lU

I -Sh Φ U -PI PI fl UP -PJ, JÏ S »1 ΓΛ -μ fl λ P £ + * Ιιΐ I t * ft PI ®, 01 II '- 2 ts ι ai« n - rs - ο ι ® £ i ι rs, H rs, wpv, in * »iica ι im un-» - ι Ç co yt χ 4 * 1 VO -4 * 1 «n -3 * 1 U * NJ u Ν.Ι ft -4 * 1 n. «'S ι ι Λ - 1 l-l'OI 01 I--. i2Hth +> C0 hm HCM HO HOOOJvOC hP - ® XX-ÄNJSei i - »o X'T + iiea £ ir-ι -PI · * - · Xl ·« ^ Ofl O fl H | i * <ι · μ H 3 v »J -h \ j.

35 3 N »l« v »l Η T3 H * 0 X Ν, Ι I -4 * 3 ^ β I Ql {aiÄlQ-HQH-PlHia · 10 I \ IN cl \ ι E l £ 3 N Xd I Cr, -μ S CO oi HOlHOim-rt m-rt, ΟΟΙΛΗ -P - = ^ Ue - I UlOl-0 »0 0l4» NUÄreT3 »-sH Φ T" X MU MU (DT * φ fl O ^ -PH {-η - h + j - o '"' 'P w, p M - 2h -μ' iE'- 'in« I KM I KM IX IX I IM I u I l * -. ο H VO V.1 rr' s »! ® 'vi tn a in j: (T Μ n (J rv ft *. ®M in so n-aa oso 40 in in in in in in ® inva 39 2 / -27- - ^ /? - board : Dr.H «ri>« tAsmis · Df.Chrisllan Bruftn - Haru-Jürgtn Htmann Postwnehrffl: SOlEHlNa AC3 · 0-10QJ Bortin eS · PoededidSIS 11? Or. Heini Hanns «- K * rl Otto Mttteistensawid - Dr. Hont WitzMats «<* - Kooto: Β * ι1η-» νβηΐ75 · «|. BnnkMtzaM 10310810 -Ϊ VoralCMdw des Auisietitanta: Or. Eduard v. Scftwartzkop (Mn Barlirwr Commerxbank AQ. Berlin, XontoHf. 108 7OT00. ICDlailTl : Berlin and Bergkamen Berlin «1WÄ0® 5 trading agent: AG CharlonenOurg SO HHB283 and AG Kamen HHH 0061 B **

• · SCHERING AG

Gmrefbßcta legal protection .27 "5

O (J (J

o O O 0 «U O 00 ΙΛ

«10 - ü O JP * Ό O

«± U s Jr * Q: 0 -ri τ-t -r *« «υ o« «0 OO> * —i ······«, (Π CO O g .... · SCMCOO 01. .. ft ft ft> * '3 ^ • ^ .. ftft & .t.fc.

* <& ft & · _ ·· · * p. &, »® · · · * ^ j: ft α ft ^

O ft b ft I

. _ ® e 15 Ή Sn -t -μ |

OS. «CO

Ai -ΜΗ C

l I «ö> * 1 i o \ ü · i λ? o, £ r »-eo ft ii 20‘ βΙ '^ ΟΙί i ff JL Ό 2 O yj N - 20 e £ e -S «« e «-? * bie

Γ iî E j β U · β 1 fi W C S

h ^ -M - · £ .p · Ρ HoW-H-H

* s i s -3? ί «-Γ8-54 4. 5 I i 2 *. è £! S Si i * Ί, *, £ § >> fl «β N * vo a eô d« “λ vo · *« oe te -ni. ? ta 5 "j * g + i H -P ι-t CM +> 25" ^; N.; > 5 i. -h o. * <>> * «· 3 r4 I in I ® t ©» N + * P Γ \ <fi M eô Ö • O Ti 'J) +> ΪΗθΐδ-Μ-ί · ι · ρ \ ι-θ S δ · 5 <c * ^ I ζ>, -H CO fa *: «I r.1 rt LtO .o» K, J CO ί ¢ 1, - LH «H ΓΝ, - -a * A 22 JL λ ^ a ^ 0 - i +3+ »r»> »« >> oi Ό i • oh J: ΐ - 'HN a, 5> S i 5 ί l 1 ΰ ί >> -sm - μ ®i «"' 2 ~ n ^ Irl £ JL -i - = * 2 -PM I ί Ή ΟΙ Ή \ l ^ »30 i 4 '. · p.' \ I?! A i I - * t $? 1 7 i si • i w. I n 15 I i è is>? I "« "si λ • S ^ i 5 2> ΐ é, i'S, S.? ' 7> 'l 3 2 Z ïï ï>' >>, il * :, g -î '- ioa \> * o ftg a «SJ f' Vr- \ ~ i Γ ^ ^ n%. X · HX -Μ I "- * ^ i fs i 'J71 Λ - JL ctf. ο β o o à ir ^ u * «u, ca -, Cl CM ® J- l | CJ u 2 I '-si i - ί ή ΐ ^ λ t s y? i «i. 's ï 4, 35 I "ξ," -; ζ, J 7 ï ~ 3 s ï 7 '7 I “ï -S 5?' 5 I «^ il s Γ * i i1 I II H L« Si CJ S-, «SN +) SJ.r2 ', vJ. n · - W · * <Ci 1> 3 · «I K'1 i« td U «« ^ H '' E 2 '-6 «-C« * ^ 2 - «« v ï * s J λ £ ί »Λ · Η ° • f ^. -rj P NH * '' '£: «Λ 2 ^ S 1 g I | £,« o g * Vft -P tn -H ¢ -. ^

40 -H! £ IV. 23 ^ C

.S „-28- rt (M en, Λ S / vo VO vo w V, - n Maaisnn postinsdirift; SCHfflINö AÛ · MMO 8« filn tf. Potlf »*« βΉ f Board of Directors: Or. Herbwt Asmis · Dr. Christian Bruhn Hsns-Jurgtn n "n" ". N. Tu. ^" I *. · "" N '-1 · - -1 "- jf —Qr. Heins Hanns» · Kart Otto Mittelstansdiatd Dr. Horst Witzal Postsdtack-Koflto : BdfHIt · “·« il /> wISt MMSiltZIM 1001 ·· ^^^ ^ ««

Chairman of the Supervisory Board: Dr. Edward v. Schwanzkoppan 0 # flinW COffltMIZtSinSC Aût Stflifl, Konio ^ t. 108700800, BwâX * ^ ® ^ —— «i SiU dar Qnellscnaft: Berlin and Bwgkamvn BafliMf OfsCOtlto ^ ankAG. Β · «!«. XOOtOWf.2fl / SÄ ΒβΜΧβ ** S Handalsragistar: AG Charlottwiburg 83 HBB 2B3 u. AG Kamen HRB 0061 Bwiintf HandetS-GeMlIaaïUt - FrtnWUfUt Sllik -, Bttlin,

Como no. 14-3B2, Baïutliirmhi uasoZOO 'a— a> ms 4 t -20' Commercial «· Legal protection

SCHERING AG

5 "<u tj

" in O

* 10 CU U U U U U OO eo «oocooooovo -PCOi-it ^ iTv ^ -CMOO i - m 1-1 CU T- tn CA ΙΛ fv. <fi \ IV- C CU Τ 'f. Η t »-fl t-ι \ fl o ·· * · * ♦ ·· ··« · «t« · f «, ······» · * * «ft ft aa ft a -aft ft • C ft ft ft ft ft ft ft ft ft 0 «15 -η

i-i

"Λ Ϊ * 1 s ft I"

* "I O fl I I I

i ('S. N -rj O * O «J

on <M - «B N o Nt, 20 i * a η« n «* H Η O“ tJ β Ό β

- S R τ4 fl I -Η 4 * I

ici η * Big 8 ι · ο ΝΙ Ο> \ Η S Ν Ή βΟ C Ν ι ^ Λ ο ο ο -ο a Ο Ό β R ο · β R A- 1 Ό Μ Ν> 1 5 * fl * -Η fl - -3 * τ («4 Λ + *>» * 0 ε> * Ό »g 5 <β« «A £» · η A - fi Η 5 Η Η · ** β -C Ο 4 Ή Ο

_ _ S Η + »J, h« t u> N R

25 5 <rl «« 0 +> R fl + »H 4 fl β 0 +» - «+ * *« S H> »

do ι tv- +> «- +» te η A

5 fl ® · l ^ P l t, -U «.fi! A - · Ό ·« 0 * I · h · co · β ι h * ^ Ä P- C * C. fi co fi -u fi - S c, p- * -u fi. a · o -s * o r *. o “0” o rv. ο o -sm «o fi U vO 1 II - i P- I + * I» ι R - + »ι - j * h -4 * ό -ï · -s * i-s'vo-a'ftcu ia *

w «-c * i fsi - ι ό ι = s I - J (-COI

ÎH I C * 3 s -3 * C -c -fi "-T C« 0 ih -fi '

| HH R H I Tl.5 * Ή Γ- H ΙτΙ I NI Γ> »H

<30> Ν 4 N H N IN - N Λ N, -, ι -N

Z - S Jfi a & 4> 1 4 Ηβνοβ 1-4 β H IN. V £ a * Ρ · 0 HH 0 -1-1 + »Ή> 11-1 - 1-1> 1— H>,«! -Tl

- I V U RR fi R .S R -S * R fiRfil ^ R

O-S "g H ft H« v HH I H «Η g H | H

-I II II ftl! Sl H | H I H - H I

j- C co ν «N o \ irv >> fN A rv x; ica> i rv (H 1-3 * 1 I -3M H -PI CO -Cl A -3 * 1 H J * I + »Ni A -4 * 1 HNH-H-O- I" H - ι - Il H -

4> i CM> »C4 >> 01 H Cl: <3CU CUClcUO OCH

HHH-H-u - >> * l- 1 »| N g - - ~ e fi R CP- · S T 'I in H ih so ih R ih R 4 ι li-i -> J <u -μ β Μ «\ l n SI ί Μ I NI 0' s.! o fl CA V »! * ftl ftl ftl I I C3 I H | ri | H H 11

ο IN O N OIN. HIN I N> fS -S IN .fi g HIN

rH -3 * 1 H U | I-H ΟI>, Ol H Ol C Ul O ul U -i> 1 ΟI

= o-ΟΙ Ο I ri I RI ®l II lOHl

. > i 01 >> H> 1 Tl HH OH .fii- in - in R HH

\ I IH I ICM I ICU t 103 I IOJ I ICU! 101 l>, I 101

£ CA ni CA NI CA NI β NI CA ni CA \ 1 CA NI CA A CO NI

"Ko"

®H CU CA J * IA O rv CO CA

ι / r-tv-rviviv-rv-r ^ iv-rv. -29- a / a / jr

Board: Or. Herbert Asmia · Or. Christian Sruhn. Hans-Jürgen Hamann Postal address: SCHEHING Αβ - 0-1000 Berlin eS - PoelWdi MOU - Y Or. Heinz Hannse · Karl Otto Mitteliensoieid - Or. Horst Witze) Postal check account: Sartln-Weet 1175-101. SanldattzWil ΙΟΤΜΙΙβ

£ Chairman of the Supervisory Board: Or. Eduard v. Schnwartzkoppen Berlin Commerzsank A <3. Sertln. Account number. 10 x 70 * 0. BenajeittaM 103 JOO

I seat of the company: Berlin and Bergkamen Berliner Olaconto-Bank ag. Berlin. Account number. m / snm. SeMdettzanl 10070000 S Commercial register: AG Chartottenöurg 93 HUB 2E3 u. AG Kamen HftB 00S1 Berliner Handeis-Geseiiacftaft - Framtlurter Bank Berlin, u. Komo-Mr. 1A-392. Benideitzanl 10030Z00 M e% * * f »

-a ,. SCHERING AG

, Intellectual Property

bO bO ta bO

c s cs 3 0 3 <J 3 3

NO N O NN

+ JT * 4J P- \ + i + ia in ο vo «« «U» N ο Ο o «o τ * om O m O = -C 0 S l 0 0 OSO l ososo 'oo <uO Ο« λ π a <r \ ri o «in on» * »ΙΛ Μ ΙΛ m« n OS) vo vo <o N Γ- S1 r- ”» Ή V CU w CU OJ Ol CU sm τ 'τι ** * _ / « we * H + »iQ S ·» * ·· ·· * · ·· m ·· · * - <5 · · * * · - »* *« · - t | +> c, p.aap.c-o.P.aft 5 * 5 b fis. &. fa. Cs. Cr. Cs. Cr. 6- Cs.

> * fi

A O

! P * Ui 1 * 0 ’I» g Ο β l *, I N U * 0 »ο β i» * <. ,? η n «« js ns. · »Jj i βιπνι-μβοιο β'β 1 *; ST <-w®co + »Tie +» Ä -7 -π Eflo +> - ® - -ο ® „r

A -5 -w s i e n- c +> iw g "fnil • h OSO CO o TOI" si a JL? T E S 0 ^ - I vo I CO I * ® IS

• H fl HA rv -3 * - -4 * - 0 0 * + * S> 1: S - I -3 * I n- N ^ iJL- s SÄOS vo S iS - C ο 'β, a .5 ® £ c. (80-y - · ΗΗ · ΗνθΟΑ + >> »Ό -Η · Ο i SS« -4 * N> «N - I τ! Β Λ" 5 ^ 1 j. -Μ α + »iewe-4 *. 4'E +, s ® .T "Τ ι ®>, ι η -π ι« η ι ι -η «*« 'τ1 ^' 20 ^ Ο 4-1 ~ e> V ί. «I * - C ou * 1 τί h S 3 - C Î *, - Æ + »a +) H-HSffl« * + “-4 * *« -n cO - Γ ~ + J | Ol ^ vNflS + · SOI »2 2 * >> c -c -c «rs. s n c «* O> e i C .2

S jror ^ ovoo S <3 * IO. ^ I «-Hj; ^ COO

5 <51 “I *» I · I · £ !. «£ * 1 ft *

ü ls · c ·? aoi a «0. +» ι * υ r- -4 * p «C

Λ, -, Il | - 1 -> s I +> -il - I S-® · T} «fi ce '' S Λ | Τ <Λ | Τ XN« O vO ST> * T'1 - s + »· Η ι · μΗ · ΗΗΝ »| Η \ ΙΟ-4 * Ι-Ρ -a à V 5

6 INHN n N * 1 >> 1 A · IJ ’- 5 ^ J MAY

"OV (8> v <8 C <5 ί N ï Ns. -U CM CO S 1" ’S * 1

j τ> - <η £ τ | «· Η« üjooio * - o - “'T1 2 _T

J 'aC. + JSiSJ! IJÎlEl'r' 'tv.lHSHIÂÎT'.

^ «+1 <u-s a *> S.T * Ο. τ 'Ί M «-CT ^ ^

5 rs_ I Pi> 11. > 1 - fl i vo ι Si C - «I

v ^ ni ι ni X nv X «mx icu i - C« <> ί *** * ^ VO 4Ί Ο 3Ί 0-4 * 1 ο -Ν, Ι 0 ^ -. 1 -4 * Ul 4 τΗ Λ- 1— \ ΙΙ «Ι ® ι - ι. ä - ä ι - ι - ι ι nr ~ 3 1 ^ 1 i H CM rH eu -iJ <M * -> 0 4J O cnr * H fl> <w J “T ^ ~>,“! *> - ® »© N UN '-' * Ή H * 5 2 1 .î 4J ir * + * lr * S 1T * S« E «1 ICM 2 'C *, 2 -2 ι 3 \ l 3 -ri NI -H fl -ri fl en N.1 3 A \ »AV t Xi ai ca ι ai q -na -w rt αι +> ι ^»

30 1 n ^ ins 1 N i £ 1 ε Ίΐ S Λ -r '"m -r -2 θ' S

—J 01 -r> 01-4 * 01 -C1 ·! -) -4 * 1-1> vN - *> —I 2 Ο * Σ -H Æ N

I SI Si - i -o-oh <5S-ii »g -2 <1“ S) T -. «JT-icnT.ensens ^ fl © w (^ T, (ni; ^ 5 + J.-4J- W -—- flv- * fl <<. RtUTW -'- 'fl ^, - rt

I ICU I ICU I ICU I> 1 I >> I E 1 | r "i, ^ A * i J

en's.icn-socn'Njen.s cn, s co-h n \ i rt \ ι π - co-n 35 h «

•H

S * <* ct * eu «λ-s * mvo r-ce ov. ^ 2 Ö Ö ce CO co CO CO CO CO ca« «/“ -30- / 2 '---- Board: Or.Harten Asm Or. Christian Brunn Hans-Jûrgon Hamann Postal address: SCH6BING AGDi Berlin 85 Postlacn 85 0311 - * Dr. Heinz Hannsa · Karl Otto Mmeistenscneid · Or. Horst Witzal Posiscnae account; Seriin-West 1175-101-, BankKleitzaW 100 tooio

î Chairman of the Au / sicntarais: Or. Sduard v. Scnwartzxoppan Berliner Commerznann AG. Berlin, Konlc no. 108 7006 00. Banxiaitzanl ICO * 0C OC

1 .- 2 «m <-___ n______i = _________ Beniner Discomo-Bank AG. Berlin. Account Hr. 241/5008. Banxiaitzanl 100 70000 4 '_ ^ 0- Intellectual Property Law

SCHERING AG

/

»« 0U H

,, 2 3 CJ + J IA

o ° ο m CO © tn 2 «œ O» t. »0

-oooSü © 0 5 $ £ S

t Ä Ä Ä f λ <, n t- · c N in CM

® ο ο o er © p * · © ο 7 i-iwi-t approx

5 'f? - o r- cm t-5 © * n £ - cJ

0 H <M «OJwi-twr-".

ή © .. .. .. ... · · p p p - H-P. ,,. . · P £ »· S« · & · 25® * a c. a a a fa "*" fa &. t * fc fa «* ·" Q "

£ p

J3 O

. CUM, 10 '. à g s s% ·! »1« ό »? ! g 2 1 o i Ό - £ -a e 2 © u ο Ή £ 'J «

W’S S fc - S * »*, x 0 S

© • Co>, o t. J, S -a 5 + »« t «fi £ Js-o 2 + 3>, 0 i Ci * 3 ο <β τι> <3 Λ. ?? 15 ® +>> »i c,>. £ λ ® * 5 i

J - S «£ · 4- -μ £ -P β« 7 2 P

r- o -p © i «© et. -g J. 3? • II UC -P Sat. * · £ -2œ «Ό -4 * β -P -H I. -P -P «f * -2®? - I »© N oo © H +> p * 7 ®"? ^ J * S NC -P «- C +» SJ, h vo-s-eo © lW - O lW Γ-0 1000 * 0 ... .2

- "Nvoreott-icOfc" · £>. i * T

-fl -j * "-p vo er --or- £ 7 5. Λ ~ · η er i r- I - i p->. -« HNvo - 1 UI 3 · NC c - 3: vo G ί S '.. - 2 ° _ 2 H Ί1 t' 5 "*! ' '5 «m ® er ο ^ o S» & î>, l 2 "T N à 2 I1 § JL 5 * ί -i

y fi -3 * 1 h · Η I · bO -h t 0 ’Λ I fj I J * I

5 ® * CÖ U ^ pH ^ U ^ I jS * ^ fl ps ^> \ fi I C

Ê £ cm α-p h nj © -p - -fl * * 7 ? 5 y, 5? a - 0 1> »1 0. 1 fa 1 fi £ f- a - S shm CH I- t, rs fi fS ON fi S« 5 '1 pj - §>, «* S'> i \ J S. e * i © er t 1, e * i ®-w - j <2 J,. “5 Î5

P λ 1 t - r- ο, -ÄS &2; S “J Γ l © U

5 * 1 N © oj c. ci 1 ci a. <s' v, Si “i ® © Ul I - H - <0 - HH XL '-S * Hl H. βΤ 23> f J. H' Cl - 'C, 1' C, * h £ ï H - î *> * ^ A ^ ® r ^ -] * cil - * P> 'H>' 7, i '^> 5 g V? ^ .1 &

5 - · IOI S N © Ps. > 1 ΓΝ. «Pn ®Î? I5H h Jl i. w o OJ

13 I \ l 5 Ul S «I C Ul S -3 * I = - P. a P. Z, - H - r \ -I Λ I II © I 1 '1 «I ΐ ^ Γ ICI I M>. Μ

1 10 a T «CM H JH CM CM fl 'l a μ o NI A \ 1 ί SI

a>. «> 1 ICM I ICM U ICM II- 1! ^, L 0 * 1 ^ (3 H rs. Ο ΓΝ.

* 5 3 S> ·? > '5>'? ? ? s ¢. 3 I S 7 '2 7, 30 S -H s§ ►. S 5S> »^ 1 ^ fi οί 1 2 ^ 7 C" '£ À% HH' .5 ^ ^ ^ T = 1, CJ 7 .Cl - ^ 3 ^ 2 w -H <· <JI Λ H C3 N ., «'S, k W ·>, 1 g Ig 1 g I ICM I! Pj flfl SO -« Λ H CO HO -. «NI © * 35 h ©

* 0. . - N C3> 0V

m u O - OJ c- \ er m'rCPCJ'Cv H ^ <3> C c \ CN OV CV 0 \! “’31 ·

"i X ~ ^ V

X / Voraund: Or. Heroert Asmii · Or. Christian Brunn - Hans-Jürgen Hamann Postal address: SCHEB1NG AG - 0-1 Berlin S5 Postficn S5 0311 2 0r. H «mz Hanns · Karl Otto Mlttelstansdmid - Or. Horst Wittel Postsciedt-Konlo: Serlm-WeSt 1175-101, BanKleitiaM 10010010 ï Chairman of the Residency Council: Or. Eduard v. ScnwarcKoppan Beniner CcmmerzDank AG. Berlin, account no. 103700600. Code number 100400 00 c Seat of the company, Berlin and BaroKaman Berliner Cisconto-BanK AG. Berlin. Account no. 241 / 5Q08. SanKleitZafil 100 700 00 4 ',

.31- SCHERINGAG

Commercial Reefitaecfiufa / 60 * 4 ° 3 ° e 5 o * ο υ cm u ο ο o ®

0 O I u 0 0 0 0 U

'"T -a" ca ο 0 o cm r- ® 2} ri Ο Ο θ' Γ * · Ο O ^ «® .. ·· .. ··“ ·· · »" “- S · ·« · · · · *, T. a c. E, c. 0. fl. C. Ft § ÊS. Fc. Fc Cs. Ct. Ct. Cs. & 1-1 + »_ aa> - Λ ο 0« Μ i® * »ο 2 +> 5 ι« Ô 3 0 £; 4 3- Ä i Ä 2 ϊ ïà'oblitti 15 * SSii $ s | g cô «· Η« * ® ££ · β * - c -pguo + * T, ti ts.01 * -H "UI" Si "- T CO 0" -a "t ΐ *"

^ N -¾ 2 I

1 3 J § £ - U * Q r- 0 r- 0

H N “I a ^ * * i y, J, vc J

a -s * -3 “fil -« -3 · «s * ve -, _.

20 - 60 iH II + * 'O fifl-C-S'C

* S i i; «® ci> .3 Ί 3. * § g'riïâÔs-SI-BT «*« * «I £. i t iC? B ° »? S i J S! i I.% · ï ^ .i Si 11 IN f & î &

U. 'w - <^ 4 I -H / · * «? CO

® C> '1 o "-' Ί« A N rt N H - I - '"t ï * N- t 3 H 3 & 3 î% *} * 1T: 5 I; £ ü S i ï i ï i s ^% '9 ï v «^ e-oJiÆi + ίΐ Oi Qi Æ J ~' λ H ICM £ Γν 0.ΓΊ. «F * x H (Vi (NC Γν β. ^% Ü 1 X f * · 0 - = 11 2 o? 'Λ?' Λ? '3 S, I τ' 1 ΓΛ" I? 1 “τ '* 1.1 J üiwri 1 CM ~ «U CM O-- 1 - ^ aj ΓΛ fCM> 1 in w JT-) X h" 3 X ICM ^ * £ * J? -, £ -a 1 ν, ι ί μ ά μ O \, 0 y £ y *> '30; ί î î; ^ ^ s N «* ·? ï = i 5 § = T ί v: iv: i« ί | * «®" B - - 3 - - -;; - 2 ^ 2

W * 0 2 -H IN.-C “w 'w d * ^ - wS

,>. I - a> «. ICM I ICM I ICM I e ^ s: yz - Λ æ CO -W ^ \ ia \ ι η M «^ v £) 'o - * 35 rt œ • r) (S. · O - · CM -3 * IAVO ζ- οι ί · oc OOOOO o Ή2 Tl T— T «Tl tt T- r« Τ 'oo <u -4 ^ -

Board: Or. Herftsrt> * m »Dr. Christian Brunn Mans-Jûrgan Hamann Postal address: SCHERING AG * 0-t Berlin OS · PO Box «S 0311 2 Z Dr. Heinz Hanns * · Karl Otto Mitlslatanscaieid · Or. Horst Wittel? Ostsen «at account: 3eriin-West 1175-101. SanKlaittaM 10010010 3 S chairman o * s councilor: Or. Eduard v. ScnwartzKoppan Beniner Commerzoans AG. Berlin. Account number. f08 7C06 00. Bansieitzam f00 Ό0 00 4 1 Sltt of society: Berlin and BergKamen. _______ 2 = 2 == ', M ™ °°

SCHERING AG

4 <_ 32- Commercial legal training

M

C.

O s λ u> ο ο «0 Ο ΙΑ + * οι ο ο ο υ« α IV -3 * ** 0 Ο «Ο 0) CJ IU \ C0 (4 T« T J3 II -3 * o 'S * ® r;

J Ü τι οί O r * Tl fj CM

Bl 0 »CA t-ι ^’. τΙ O CM · ... ·· ·· H +1 ·· ·· · · · · <0 c ♦ · a a a 0.

us; q, a ta, Ce, fa fe.

• H + "6fc fa tQ" SC J3 O a, "* 10 •" · O O .2

U W | IN

* 0 I * 0 · Λ ««

So S U Je λ «a +» + »* ä <a as β« ® δ

U * β V. + * + »** J

15 U -rt +> I J, O

0 g «CO CO h -» Jj „J ·. ·· ”1 O I ^ C ^ £ _â CO 1 * CO -O 0 ·? - -a - sO I vû 1 β A- SA * "* J *" ΐ h -, £ '-y 1 -3 · I +1 VO «vo C t C lc ® -CU - 0 il -HH -h T> <rc + * -c 1 sssn __ II «iJ * bO®M« ° 0 20 _ τι -r + j rn 1 u * a T * - g ïa 1 t sceue ^ A '«bocco r -ha c . -tJ - 2 * U -H - + »ΜΟΐρ ΐνΟώ 5 eNP ^^ eeUAsUrv -g B c. c -s S -h a -ri a -3 · ι -c * ® Έ ο -h ό? 1 u 1 “JL ΛΓ 1 J» a uu - J, so-u co cm cooj

* ”C, j · j - il 1» I ** 7 J

* P Il 1 'T \ T | TI T | r <S 5

H s \ Λ ί H -3 * 1 r-l "aJ Tl ^, 1 S J

® 7 2f | H * dS-Sl> .ieg. πόα + »^ a - ôüicoiarj, 5 X.r.S ^ AV.1 a-C. ^ 07 v O \ I A 7 01 o - O '7 ri.

"X; 1 0 1 h. in. h 101 <i îw -C v * 7, 1 O rv h rj, O Ol O V.I o 7. » Ο B 01>. f «~ U 0 0 0 Ci d 2>, T, o r-i ^ ^ a ^ y w, τΐ 0 -.- 4. s toi se se 1 t <icj s «7i £ x: -o -c v 77 *

30 S \ l -S "7 τι -P -rj 7 - J pL

I- ^ 0 «f * T, ÂNS * H? «I 1

: C N s: V I a 10 1 c H I

r * Ό r * J * "7. w '* rt * 0 w <î - w .h w ^ I £ I s · £ JL! £ *.

I 5 I | CJ, Λ Ή CA £ ο «CO

CA -H CA "* 35 H®

* 2 - Ο Ά CM CA

a · co cr \ z. ^ ^ th - 2 2 -33- «g / ®

- J

’Qy 'Board: Dr. Herbert Aemis. Or. Christian Bruhn Hans-Jürgen Hamann Postal address: SCHERING AG 0-1 Berlin iSPostfach 65 0311 '1 Or. Heinz Hannse · Karl Otto Mittaistenscneid · Cr. Horst Joke »! Psstscneät-Konio: 3erlin-W «st 1175-101. Binkleitzsnl 100 10010 3 Chairman of the Supervisory Board: Or. Eduard v. Scnwartzxopben Beniner CommerzbanK AG, Berlin, account no. 108 70Οβ 00. Bankleitzani 100 400 I Silz of the company: Berlin and Bernnam.n Berliner Oiscomo-Bank AG, Berlin, Konlo-Nr. 241/500 «. Bank code 100 700 00 «

. SCHERING AG

C «w * rbiioi« f Legal protection “The following examples explain the possible uses. of the compounds according to the invention, which took place in the form of the preparations indicated above.

10 1 r 15 -34- 20 25% 30 • Γ 35 40 Â *? /} fl w / '' 'N. Executive Board: Or. Herbert Asmis - 0r Christian Bruhn rians-Jürgen Hamann Postal address: SCHEH1NG AG · 0-1000 Sariin 05 * Poattedl450311 w? N ^ r. Heinz HannsKan Otto Mitteistenscneid 0f. Horst Witzei Postsoiaac account: 9erlin-West 1175-101, Sanfctettxanl 10010910

'. * Chairman of the Supervisory Board Dr Eduard v. Scnwartzxoooen Berliner Commerzoank AG. Berlin. Account-ftr. 1® 7006 00, BanttertzahMO

I c "T Amt n", "" .mrf Berliner Oisconto-dank AG. Berlin, Komo no. 2A / 5D01 BanKieazart 100.

3 Commercial Register - AG Charionenourg 93 HOB 233 c. AG Kamen HflB 0061 ia / aSSÎ “0“ * sa ce ««

, 4- SCHERING AG

G «w * ifciieh« r Rscfrtxidurtz 5 EXAMPLE_ll4

-J

In the greenhouse, the compounds according to the invention listed in the table were sprayed at a rate of 3 kg of active ingredient / ha dissolved in 500 liters of water / ha onto Sinapis (Si), Solanum (So) and Setaria (Se) * 10 as test plants using the post-emergence method.

3 weeks after the treatment, the treatment result was rated according to the evaluation scheme 0 to k, where 15 0 = no effect k = destruction of the plants *. As can be seen from the table, the test plants were generally destroyed.

25 • -35- 30 35 / / UT Board: Or Herbert Asmts Or. Christian Bruhn Hans-Jürgen Hamann Postal address: SCHERING AG · D-1000 Berlin 48 - Postfach880911 - * 2 0r. Heinz HannseKarl Otto Miuelstansaieia Or.Horst Witzal Postsettedc-Komo: Berlin-West 1175-101. BanfctttzaM 10010010 j · Chairman of the Aulsiousrat: 0r. Sduard v. Expnxxen Berlin CommeaMnc AG. Berlin. Kooto no. 106 7006 00. User 1004 | 5 seat of society: Berlin and 3erç * amen 5 * rt, ner Benin. 10QÏ00 5 Commercial register; AG ChaHottenourg 33 HRB 283 u. AG Kamen HBB 0061 1COÄOB ““ *

SQGCfV

* ·

»I

-35- SCHERING AG

G * w «H> lidw Rachtsschutac

Post-emergence according to the invention

Compounds Se Si So 8-methyl-3-phervyl-4,6 ^ 7,8-tetra-4 4 4 hydroimidazo £ 2, l-c / £ l, 2.47 triazin-4-οπ.

10 3- (3-methylphenyl) -4, £, 7 t8-tetra- 4 4 4 hydroimidazo £ 2, l-c / £ l, 2.47 triazin-4-one.

"8-methylsulfonyl-phenyl-4,6,7,8-4 4 4 tetrahydroimidazo- ^ S", 1-67 ^^ 1 2,47 triazin-4-one 3-tert-butyl-8-methyl-4, 6,7,8- 4 4 4 t etrahydroimidazo- £ 2, l-ç7 / 1,2,47 triazin-4-one.

3-tert-Butyl-8-methylsulfonyl- '4 4 4 4,6, 7,8-tetrahydroimidazo £ 2, 1-7 £ 1,2,47triazin-4-one 20 3-tert-Butyl-8-propargyl -4j_6.7.8- 4 4 4 tetrahydroimidazo £ rr, l-ç7 £ l, 2.47 triazin-4-one 8-chlorraethylsulfonyl-3-phenyl- 4 4 4 4,6,7,8-tetrahydroimidazo - £ 1 £, lc / £ L, 2.47t riazin-.4- one 25 8-allyl-3-phenyl-4,6,7,8-tetra-444 hydroimidazo-ZT, l-ç7 £ 1,2 , 47 triazin-4-one 3-i4-fluorophenyl) -4,6,7,8-tetra- 44 4 hydroimidazo- ^, 1- ^ 7 £ J, 2,47 * triazin-4-one 30 8— ( 2-butenyl) -3 ”pbenyl-4,6,7,8- 4 4 -4 tetrahydroimidazo- / 2, lc / £ I, 2,47 triazin-4-one 8-methoxymethyl-3-pbenylj4,6,7 , _8- 4 4 4 tetrahydroimidazo- £ 2, lc / £ l, 2,4 / triazin-4-one 35 3-phenyl-6,7,8,9-tetrahydro-4H- 4 ^ 4 pyrimidino- £ 2, l-ç7 £ l, 2, .4 / -triazin-4-one -36- · ^ 0

Vorsund: Cr. HerOer, Asmis Or Christian Brunn Hans-Jürqan Hamann Poitansdirrft: SCHERING AG D-1CG0 Berlin flS · Poatfadi «58311 -" f Ornamz rannaa Karl Ono Uittamanaataia Or. Horsi Witzal Postschecx-Kcmo: Barim-WM «1175-, 01. BanUlCAM J Chairman of the Aufsiausrata: Or. Eduard v. ScnwertzKOOOen Sernner CommerzoanK AG. Berlin, Account No. 1QI7Ό0Ι αα, BankktttzeM 10 I Headquarters: Benin and Bergkamen B # r |, ner Oi * con «o-eank AG. Berifn By wrtmw 100 ^ S Commercial register: AG CftariortenOurg S3 HflB 2B3 and AG Kamen HflS0061 Berliner Handeu-Geeetistftait ββη * -, Sertln, ® Account Hr. 1 ^ 362, Bannienzaftt 1W »20 JO OC p« · • ♦

_36- SCHERING AG

Commercial legal protection 5 Post-emergence according to the invention

Compounds Se Si So 9- (2-butenyl) -3-phenyl-6,7,8,9- 4 4 4 t estrahydro-4H-pyrimidino-Z2, l-ç7 £ L, 2, .4 / triazin-4 -on 10 8-allyl-3-tert-butyl-4t6.7 »8- 444 tetrahydroimidazo-, £ 2, lc / • '/ ΓΓ, 2 t> 47“ triazixi-4-one 8- (2-methyl- allyl) -3-phenyl- 444 4 4,6,7 "ö-tetrahydroimidazo-ZT", lc // Ύ, 2,47-triazin-4-one 3-phenyl-9- (2-propenyl) -6, 7_, 8.9- 4 4 4 5 tetrahydro-4H-pyriraidino- / 2, l- <£ 7 / T, 2.47triazin-4-one 3- (4-fluorophenyl) -8-methyl-444 4.6 , 7 »8-tetrahydroimidazo / £, l-s7 ZJL, 2, jjt7-triazin-4-one 20 3- (4-fluorophenyl) -8-propargyl- 444 4.6.7.8- tetrahydroiraidazo ^ jjT, l-.s7 ^ Γ, 2.47 ~ trxazin-4-one 3- (3-methylphenyl) -8-propargyl- 444 4.6.7.8- tetrahydroimidazo / 2, l- £ 7 / 1,2, Jjfe7-triazin-4-one 8- Methyl-3- (3-methylphenyl) - 444 25 4,6,7,8-tetrahydroimidazo / J, 1-Î7 / 1,2,47-triazin-4-one 3-tert-butyl-9 ~ «methyl- 6.7 »8.9” 4 4 4 tetrahydro-4H-pyrimidino ^! R, l-ç7 / 1 ", 2,4 / -triazin-4-one j 3-phenyl-9- (2-propynyl) - 6,7,8, _9- 4 4 4 '30 tetrahydro-4H-pyrimidino / 5, lc / / T *, 2,47triazin-4-one i, 3-tert-butyl-9 - (2-propynyl) - 444 6.7.8.9- tetrahydro-4H-pyrimidino ßi, 1-S7 / CÏ, 2,47triazin-4-one] »3-“ cyclohexyl-4,6,7,8-tetrahydro- 4 4 4 imidazo- / 2, l-c7- / î, 2,47-triazin- 4- on 3-isopropyl-8-methyl-4,6,7, §- 444 tetrahydroimidazo- / 2, l-c7- / l, 2,47-triazin-4-one -37- 40 Λ / «f ·

Mind: Or. Herbert Asmis · Or Christian Sruhn Hans-Jürgen Hamann Postal address: SCHEHING AG · CMOOO Berlin «· Poetlad,« 0311 -, / i Or. Heinz Hannsa · Karl Otto Mmelstensateid - Or. Horst Witzei Poslsdteat account: Berlin- West 1175-10 ,. BenkteitzW, 10010010 ’- Chairman of the Supervisor: 0r. Edward v. Sdiwartzxoppan Serliner CommerzoanK AG. Berlin, account Mr. 108700800. BantdaitzaM ICO *

| Company headquarters: Serlin and Sergkamen Berliner Disconto-Bank AG. Benin. Komo-Nr.2,1 / SOOS, SanUeitzarW IdeTQC

5 Commercial register: AG Charloitenourg S3 HRß 283 u. AG Kamen HRB 0061 Berliner Handels-Geseilscnaft - Frankfurter Bank -. Berlin,

u. * Komo-Mr. 1A-3SZ. Banueiaant tOdSOZOO

sa ec iv

SCHERINGAG

_ ^ 7- Commercial legal protection f * 5 Post-emergence according to the invention

Compounds Se Si So 9-methyl-3-phenyl-6,7,8,9-tetrahvdro-4K-pyrimidino- / 2, l-ç7- / î, 2 »47-triazin-4-one 4 4 4 3- Cyclohexyl-9-methyl-6,7,8,9-tetrahydro-imidazo- / 2, l-c7- / l »2,47-triazin-4-one 4 4 4 10 3-cyclohexyl-8-propargyl-4 , 6,7,8-tetrahydroimidazo- / 2, l-ç7- / î, 2,47-triazin-4-one 444 3-cyclohexyl-8-raethyl-4,6,7,8-tetrahydroiraidazo - / 2, l-c7- / l, 2,47-triazin-4-one 4 4.4 «- ** - - 3-isopropyl-8-projjargyl-4,6,7,8-tetrahydro-imidazo- / 2 , 1-C / - / 1,2,47-triazin-4-one 4 44 8-allyl-3-isobutyl-4,6,7,8-tetrahydro-imidazo- / 2, l-c7- / î, 2,47-triazin-4-one 444 9-allyl-3-tert-butyl-6,7,8,9-tetrahydro-imidazO- / 2, l-ç7- / î, 2,47-triazin-4- on 444 3-tert-butyl-6 (7), 8-dimethyl-4,6,7,8-tetra-2q hydroimidazo- / 2, l-c7- / î, 2,47-triazin-4-one 444 8-Cyclohexyl-3-phenyl-4,6,7,8-tetrahydroimidazo- / 2, l-c7- / î, 2,47-triazin-4-one 444 3- (2,5-dichloro-3 -thienyl) -8 (1) -methyl-4,6,7,8-tetrahydroiraidazo- / 2, l-ç7- / ï, 2,47-triazin-4-one (mixture of isomers) 444. 3- (2,5-dichloro-3-thienyl) -8-propargyl-5 4,6,7,8-tetrahydroimidazo- / 2, l-c7- / î, 2,47-triazin-4-one 444 3 -Isobutyl-8-propargyl-4,6,7,8-tetrahydro-iraidazo- / 2, l-c7- / l, 2,47-triazin-4-one 444 3-tert-butyl-8-methyl-4 , 6,7,8-tetrahydro-3Q imidazo- / 2, l-c7- / l, 2,47-triazin-4-one 444

Hydrogen nitrate 3-tert-butyl-8-chloromethylsulfonyl-4,6,7,8-tetrahydroimidazo- / 2,1-C / - / Î, 2,47-triazin- 4- on “4 4 4 6 (7), 8-Dimethyl-3-pbenyl-4,6,7,8-tetrahydro-imidazo- / 2, l-c7- / l, 2,47-triazin-4-one 4 4 4 6 (7) -methyl-3 -phenyl-8-propargyl-4,6,7,8-tetrahydroimidazo- / 2, l-c7- / l, 2,47-triazin- 4-one "4 4 4 3-tert-butyl-8-methoxymethyl- 4,6,7,8-tetra-hydroimidazo- / 2, l-c7- / ï, 2,47-triazin-4-one 444 40 "/ -38- · C Board: Or. Herbatt Aemit Or. Christfan Bruhn · Hans-JOrgan Hamann Poiiansdtrift: SCHEflING AG D-1000 Berlin «S - Postfach 480311 - '? Dr. Heinz Hanna · - Karl Otto Mittelstenscneid - Or. Horst Wltzel Postsdiedt account: Bertln-WestTlK-ΙβΙ, BanidettziM 10010010 5 Chairman of the Supervisory Board: Or. Eduard v. Scftwartzxoppen Berliner Conu.iefZt> anlc AQ. Benin, Komo-Hr.K * 70 »og, BanUaitzaN 109aoei 1 Registered office: Berlin and Sergkaman 10070303 s Commercial register: AG Charlottenourg 33 HHB 283 u. AG Kamen HBB ooet uSaftmSeSS wfSSÏn "** ß“ 1fa · icaocrraat t *

'I

SCHERING AG

_ 3g_ Commercial legal protection 5 Post-emergence according to the invention

Links. 5e Si So '8-methyl-3- (2-thienyl) -4,6,7 »8-tetrahydro-inidazo- / 2, l-c7- / î» 2,47 ~ triazin-4-one 4 4 4 3-isobutyl-8-methyl-4,6,7 »8-tetrahydro-imidazo- / 2, l-c7- / î» 2,47-triazin-4-one 4 4 4 10 8-allyl-3-isopropyl -4,6,7 »8-tetrahydro-imidazo- / 2, l-c7- / i» 2,47-triazin-4-one 444 | 3- (2-Hydroxy-l, 1-dimethylethyl) -8-methyl-i 4,6,7 »8-tetrahydroimidazo- / 2, l-ç7- / î» 2,47-triazin-4-one ”444 3- (2-Hydroxy-1,1-dimethylethyl) -8-propargyl- * 15 4,6,7,8-tetrahydroimidazo- / 2, l-ç7- / ï, 2,4 / - triazin-4-one 444 3-methyl-8-propargyl-4,6,7 »8-tetrahydro-imidazo- / 2, lc / - / l, 2,47-triazin-4-one 444 3-cyclopentyl-4,6,7, 8-tetrahydroimidazo- / 2, l-c7- / l »2» 47-triazin-4-one 4 4 4 20 “” ”“ 3-cyclopentyl-8-methyl-4,6,7,8-tetrahydro-imidazo - / 2, l-c7- / l, 2,47-triazin-4-one 444 »3-cyclopentyl-8-propargyl-4,6,7» 8-tetra-hydroimidazo- / 2, l-c7- / l »2,47-triazin-4-one 4 4 4 8-allyl-3-cyclopentyl-4,6,7» 8-tetrahydro-imidazo- / 2, l-c7- / l, 2,47-triazine 4-one 444 25 “3-tert-butyl-8-ethyl-4,6,7» 8-tetrahydroimidazo- / 2, l-ç7- / ï, 2,47-triazin-4-one 444 * 30 *. 35/4 ° -39- “0Uj / Ü Board: Or. Hertmrt Asmis · Df. Christlsn Bruhn Hsns-Jürgen Himmnn Postal address: SCHERING AG · 0-1000 Barlln« S - Po * ti «di 05QJ11; ? Or. Hainz Hanns «· Karl Otto Mittetatanscnaid - Dr. Horst Witz «« Poaucnock-Komo: Bertm-Waat 1175-101. SankWtzaM 10010010

* Chairman of the Aulsiciitsrat: Or. Eduard v. Soiwsrt2koDpen Berliner CortwnefTOanK AG. Berlin, Konco-Mr. 108700800. BanidettzsM IflMC

* 3 et »· j— / + ___ h -», - **. , .λ / 4 Berlin DJseomo-BenK AG. Berlin. Xonto no. 241ÆOOB / Benfciettzaftl 100 700 · § Æott ^ 0rÎf ^ nB3H U AG Kamen HRBOMi Berliner HandeJe-Geeellecnaft - Frankfurter Bank -, Berlin, 5 Commercial Register: AG Ghartottenburg 93 HRB 283 u. AG Kamen mrb omi Knnto-Nr. 14-30. Senwertzani 1002000 «rr λ ·« V.

• · * j

I 'SCHERINGAG

Commercial legal protection -39- 3 G <* «3 * j—« «<“ <*

U

ri

T C

(-1

U

- - ®. > ^ -3 * -3 * -3 «-3 * -3 * -3

tt-l tfl - * -C

3 a] I ** i V «3» 10 «and .5,5- _ ^ - = -s * .3« -3 * -s * -3 * -s * 2 W - * * 3 * 15

O

«C * 3 1 I 1 yy |

Il I β ο g O

i i. ° i, £ 5 2 suiiîtilî.o'e 1 ® U 0 * 0® O> »f. ^ ο V m ^ >> + * U ß X * 0 ^ 20

3 5 ^ «j 5 ^ ß ^ · Z & ^ u a H

5 o u. ? i o *> r- o «i ®? o s So ^ 'aoi® -i t, c +> £ + »

£ N. ^ ’·? ^ Ό J · * * rf l * T

s. - · U _ J3 «0003 * 3 * 3 -W« 5 - 3 i -3 S «® N ^ TÎ '? '^ J, ï ^ 0 CO rs-o

I U H, 2 -ΝΙΝΙ—. N eo kl. I ·. . I.

j · .μ “Ö Ji .2 ^ ®" - * - ® * ** vO * 3 · rv_ 0 * 3 * · iatt I -H so i I - I 1 _., J .. g H- £ ^ ο T11 * - C 1 ^ “^ -s'Cvo J * c *> 2 i +» vO -3 * 1 i-h '^, 5 5 * S «g 1 S>. £ £. C * I» *>, i * N.> * «I 3 N 2

Μ - Ο Γ * - 5 I - 2. * 7 tL ΐ £ 1 "“ T * ^ 0 M -H

3 i 3 - ® N "O M C ^ 3" H'nIjsv * jf S5

Ό £, .. · ', "3 - <U 1 a -> S 1 a I ci c. I

C «3 -3 * 5 -i ni f1 'Ci a ji>. C, S il 2 Ci. «B 0 rv * 2 * S J, t * £ '« * - j: ι λ - a - o. A q, - S S>. 2 S i g w. Does N. i fJ £ S? «30« «h 5 h i j, h V 5 i?’> I μ 1 lr: gi «;

- £ ® V. S - £ ~ * X «'^ JS ~ XI £ i Js \ I

Λ1 fs, j S I M 4J] c2 in * i r * λ ï ÎC ^ S rx w jci fi rs * rs û) r ^ v r \

S vo Ä> i S ü. 3 nights ! C VI

= 1-ΐ 5ΑΡ * ΙΓΛ | ίΛ | <* <U 1 l-® | j ® '-i «' ^ <pi.®ây2'T '^ Jl3 ^ iTl-r’- nc \ ij3- <

° B ί, t <$. ^, J 5 2 *? '«Ï«' "2, h" "I ir" i U ICM

i J -5 ^ T o -i 5 .h J, r S 3? ° 7 V o> '! 35 3 ^^^ Γ-ι ^^ βΗΛΟΦΒΗΙΟ-Ο H N 2 i 'c î-i i- *' P d-Sj. i * «• H ®. - a, w - ^ h. ci ^ 3 ci ^ HT * <· "3

U i ICJ I '£ ii £ Λ ί1 J. S X - J, J' S l KM i E

£ 3 v ^ i r * s Î ^ # ficC * riCÎ5 ^ CO ΓΛ * rt ςτ \ ^ ^ L · - · 40 '* U Chairman: Dr. Η · γβ · π Asmis · Or. Christian 9runn Han »-Jûrgan Hamann Poaianscnnn: SCHERING AG - Ol Serlln« 5 · Poartach «50311 i 0r · Hamz Mlnna · Karl 01« Mineisienscnaid Or. Horst Wittai Posacfteet-Kenio: B «riin -WMt 1175-101. 3ankfeitzanM00i0010 4 Chairman of the Aulsiditsrat: Or. Eduard v. Fast forwarding to Berlin Commerzoenk AG. Berlin. Account number. 108700600. BanKiaitzanl 100 «B Registered office: Berlin and Berokamen Berliner Oisconto-Sanfc AG, Berlin. Como no. Z5ir5008. 3anweitzam 100 700 - '.6 Commercial register: AG Charionenouro a hflB 2S3 u. aG Kamen HR3 0081 Berliner Hendeis-Gesellsonaft - Framt / urrer Bank -. Berlin.

W ^ r SCHERING AG

Commercial legal protection H 4 · * · * U U) -5 * -5 * -S> -5 · -

^^ B

^ B * T -s * -a * -3 * ^^^ B s en 'S *> s * -s *

^^ B

J * -5 * -3 * ^^ B -j * Î ^^ B Zen -fl * sp

^ B

H 2 ΐ 2 ^ ^ B .2 2 £ g ί $ ï Ί * ^ B u> <Έ, -c λ 2 ® ® -s * c ^^^ B h? ? o, 3 H + »+>« 10 î i a s. * i b ic s i a

^ B e-fi-2 ü 2 ° - 0 · O, O -H

'g 7 f CO 5 vO I' β I CO U N

0 yr IV »-S *» -3 "O JS

^ B, - * J, Œ_ ® Γ'- yy -s * I? I 0 -A

^ B 'l' ’* 5 ^ OCißtS-fiHl ·, ^^ B - è ^ e ^ - vû Z -o H-H -Η · Ηοου +> ^? vûo ^ Cÿ I -S * fcû β Μβ gps, ^^ BT [g _, J, Si *> T1 · 'U -ri U -H 11 H -3 * 1 ^^^ B £ e -a · «* . ’Ί ^ h j *. >> g β «eu ^ e> L · ^^ B u'Î'i <'>, i te -C'H a +» c- h -wx: ca ^ B e ailn-S 7 ü te C - * t »01? J * «* + * - S 5. Tl *> »· * u ·» - «_ - oe Sa rv ii (s -u« «h

^^ B - S, g * · £ * g - N £ N ^ g 2 -H a -s * i A -s * i C * HM

e orvxe - ^ «c-Æ n 7 i t <1 *« UII

^^ B 5 i ~ * 'ï 7 * ®-w q -ri ^ 1 cov co «com a-w ^ rs.

tj ΤηΓηΤ! = * - · j_ s- i "i-oiioi r J, W ° T * lW a · ^ i 1 -> fv ~ H * AI ** rtis h | * * 5- | _Γ Ή (J 60 _ g ifS "! 1-1 -, 1 ^ Xl gJ * 1 Ο τΐ Λ 'H. * 2 ?. 1 IN 03 N ^ •' i> 1-> ι t >> 1> - rt -

U C M ^ | -s * l 1 5 + »<M -wrv ^ (N Ufl ritM

g 'i' «" T * - 7 g -s' C o i S u · -t. ον, ι ä S1 S ° i i N. H, «ί ΐ IT,; 3, | i i * r, 5 i

. ·; 5 '”,! F X, - I, ^ 0>' Ö - O - =>? S

Si n «^ ·“ Nl a S1 Ö Λ H ^ ^ 101 '? Μ 1: «5 1CT 1 'o' £ ·% CT | u ü, o "O ü \ i 5 o, - -a

^^^ B B "£ ;,? H | Vn orv o> ii> i> 'iica-H

ÿ “u 1 ^ ΟI> i, -J 0« 00 OOririwg ® 2 T iî "->.« >> «ΙΙΜΠΟ g, * is '- ►» «u ^' Ti · * ^, J5V.J-- 0: TJ c-Wi I t,

S ^ 5 7 ^, g · «, 5 ICJ ί 7 '- I 3 S * -g,? rl | "O

3 S 3 Λ 7 ’2> *> · ^ · ί J. · 0 ® S ο Ξ ho> i >> Έ« S> -. o + j o 3 A o’oiaSS'HS-h ^ n + 'Æ

.i I ^ -W ^ N: <i S 2 I> <S 10 I ο M s Ο (I

C J, g g «I« 3, S 'J- - - i --3 ü II

i- - - 7 ^ -H · ~ -Z '-'3 <.? - <; + J

^^^ B a Έ,, g T "bw '2" "Γ ici 1 = i>> * ι = i ® Λ - œ-5 Λ -μ Λ .S Λ ^ -« ** »jo η -« · Π «-u« and: Dr. Heroen Aamis - Or. Christian Brunn - Hans-Jürgen Hamann Postal address: SCHERING AG · 0-1 Berlin SS - P.O.Box 65 0311> · “> * Hanns · - Karl Otto Mmaiswnsenaid - Or. Horst Witzal Postschectt account: Berlin-West 117S-101.Bank code number 1001X10 sender of the academic council: Or.Eduard v. ScnwartzKoopen Berliner CommarzöanK AG.Barlin, account number 106 T006 00.Bank code number 1X jqo

dar Qeseilsxalt · Berlin and SerdKamen Beniner Oiscomo-BanKAG. Berlin. Account number. 241/5000. Bank code 1X7XX

. . . «* Afc ^ ______. right aa iinnnu. Hall .. ·· UanNAl *. / ÏAeBtleH (eleven _ Ceexirllinar Partir _ Serlln

-41- SCHERING AG

Commercial Legal Duty * 5 EXAMPLE 115

In the greenhouse, the plants listed, before emergence, were treated with the compounds to be tested at a rate of 0.4 kg of active ingredient / ha. For this purpose, the compounds were evenly applied to the soil as aqueous solutions or suspensions with 500 liters of water / ha.

“Three weeks after the treatment, the treatment result was rated according to the evaluation scheme 1 to 10, where 0 = total destruction and 10 = no effect.

20 Show the results. » that the compound according to the invention, in contrast to the comparative agent, had better tolerability or activity.

25 -42- -30 35/40 'Sr Board of Directors: Dr. H «rb« rt Asmts · Or. Christian 3ruhn - Hans-Jürgen Hamann Postal address: SCHERING AG - D-1000 Serf in 65> Poetfadi 68 0311 • z Or. Η · ιηζ Hannse Karl Otto Mineutenseneid Or.rtomt Witzei Peiueieöt-Kcnto: Beriin-We «1175-101. Sankieltzarri 10010010 .2 Chairman of the Supreme Council; 0r. Öduard v. Sciwaruxoppen 3 «rim« r CommerzüanK AS. Berlin, account no. 108700600. BanidwtuM 1Π010Γ i seat of Geaellscnart: 3 # r (m and Sargxaman Sarlmar Oiseonto-Sanie AG. Serttn. Komo- * r. 241 / SJQ8. BantdatizaM 100 700 û 5 HandtUregister: AG Ciiarlorienourg 93 HHB 283 u. AG Kamin HR 0081 Berliner Hanoeis-Gesellseiaft - FranKfuner BanK Berlin,

2. Account no. 14-382. BenMetaanl lOOSBOO

* · *

· SCHERINGAG

Commercial deer protection -42- 5 et

10 Λ CM H

, o

snuioaQ ο O O Q

• ö *

Boxqsouxqaa O O S

. o O

B ° d O O H "

- ° O

snanoadoxv Ο O Oh

15 e-m * ea Ο® OH

o BTtreqsag 0-0

Baouiodi ο O ö o S

_ 3 O

«Τ ° ΤΛ O O OH

C / ο o Q o 9 20 BTJiaxiadS Ο Ο O Oh STdBUTS Ο Ο O m q q g in o

sxay * m Ο H

o o ^ ITSK - e s s 0 o

Xajjo ^ BX S h Λ ~ j o o

__ ö *** H H

25 eCoc Ο o ®

3 H H O

Γ "e * * cs γΓ σ '* 01 <d £ i -«' lo i Γ-Η, «H?, J, U i.

«-VÎ <Ο β ΙΛ CM

3o ^ .¾ iik «

- © · I SO 0 J3 -d d I I

1 H Iß d Η ί I H o * h »hh ^ S <«> 3h> »W. f -Η o w - Ä V? w 3 +>

+> I 4 * 80 U ** HÄH

© o S ^ IC-d1 · ·> »« g n fl ^>, rr, *> + »j: ö i © i y & J" +> i, +>

! ": s CO S (? sat, ä i Hö®C

-e 5 1 1 Tl Jh 'μ ’C S-PSOH

35 tu h s 2 ^ 2 S r ®iii h fco >> h c> i-3 * c? aM * -1 £ vonin ® “» fco -p ο i *> "l + j" uiii r fcos 3 t, -ra 2 i- 2, i hcosc ß ß α tisss «η © 3 TS 1 ·>» ß I Λ - 01 4 Ή © N, 3 -ce -pr η + »λ-λΊ rpi * => 3 © © © • H tr © nu« 'u <r -P r • h λ aua 9 u ci' oiht , s «Ht, .p .μ -h -P -P '** * t <ri> P- · © -pp). _ t © i © t i 1-- --1 -43 ". , "A> (ys / //^TO* timed:0,.Hwb bidiAa,« .. Dr Chr.Mian Bruhn Han.Pürg.n H.mann Ρο, αη «* Ί«: SGHEH1NGAG · D- lCCO At «· PoWMl *« 11 i? Or. Hem? Manns «- Kan Otto Mitteistenseneid - Or. Horst Wittel POätSCfteCX'KOniO · Beflin-West 1175 * 101, FlTltlefTT ^ H 1Û01ÛÛ10

Λ Chairman of the Supervisory Board: Or. Eduard v. ScnwartzKoppen Berliner Comnterzöenic AG, Berlin, accounts. 1Qi 709 (8, flintietzWlf ItB 4tfl C

1 Site dar S «uiiMhaft: Bernn und Bardamen Bwllnar DlaeflrUO-eaflk AS, Bariln, KontoHr. 2 * 1/50 *. StnUWCCWH 10O7DOCO

5 Commercial register: AG cnanonenourg 93 ΗΗΘ 223 u. ag came HRBooet Berliner Handeie ^ seeetiscnaft - FranKturterenken -, Berlin, * “* Kont & ^ r. 1A-G62, BenKietOiitl 10020200

SCHERING AG

j Commercial ·! · Rechtuchutz t l · ’* * j. > '5 EXAMPLE 116 1 ^! In the greenhouse, the plants listed on the

Treated with the listed compounds treated in an amount of 0.4 kg of active ingredient / ha. For this purpose, the compounds were sprayed uniformly over the plants as an aqueous solution or suspension with 500 liters of water / ha.

* Three weeks after the treatment, the treatment result was rated according to the evaluation scheme 1 to 10, where 15 0 = total destruction and 10 = no effect.

Here too, 3 weeks after the treatment, the compounds according to the invention show a high selectivity with excellent activity against the weeds. The comparative agent did not show this selectivity.

25 -44- Λ 3 °

M

3-5 Λ k0

! / K

Board of Directors: Or. Herbert Asmis Or. Christian 3runn Hans-Jürgen Hamenn Postal address: SCHEHtNG AG 0-ιΰοο B «1ln« 6 - Poetfedl «0311 f 2 Or. Heins Hsnnie · Guy Otto Mittelstensaieid Or, Horst Wittel Postsäietdt-Xonto: Berlin- West 1175-101. BenitMtzafti 10010018 -Ï Chairman of the Supervisory Board: Or. Eduard v. Serxiner Commerzsenk AG, Berlin, account no. 108700 (00, BanklerUM 10040 | Registered office of the company: Seriin and Bergxamen Seriiner Oiscsmo-Bank AG. Berlin. Komo-Ttr. 241 / S008. Benklettzs «100 7» t 5 Commercial register: AG Chsriettenourg 93 HRB283 and AG Kamen HPB0001 Beniner Handets -Geseilsdiaft - Frankfurter Bank -, Berlin, and Kpnto No. 14-302, Banlüeitxenl 100 202 00 1 sa ec tv r

^ SCHERING AG

- kk- G • promotional · «'legal protection 5 10 * u 15

«0 <£ Ο Ο Ο Ο Ο O

H

stumoado-fY ο ο Ο ο ο o

Ba-ina ^ na ^ ο ο ο O ° © 20 * τ «? Λ ο o o ô ο o

H

ΒτατΒοτας, Β ^ ο Ο Ο β ο o BTJT3Xtaq.S o o o O o o

2 ° 2 2 5 ° H

CO

25 ___ o o o o «o o

UaZT3 / 4 Η <H H * e j? H

I PS

I -e * l -f-s »'W

I - Γ ~ 3 * Ι I oil I rt Ä I C3eu - 0 * ico «a:» - VO M * H. .f * 4 * 7

NH. *H. "O," (v-'Vi 'I

-'nI -R * "n '-K -, g ·» VÄ.N »I iS. r' - 'vJ U3PS ® I - 30»' U | Η Ol - 0 -οι Λ in 03 • 4 * 1 > »IC -d <, 2nd

IH W) H I H | -. "5 -3 * H

H, - U. - H ^ 3 H - g * · slca 5 Im> * h> * H · ho

-V ft "Nj JS I fi ÄVl W - ^ H

-μ I 01 -P ^ O + JJ W «PÄ 0) 0 U 0 * U l Q Ô 3 ^

® E «« = * N Η · * - * = I »* 2 Λ H

, S I «J I <8 I 0.1 i a · ♦>» Z ca t «C Ό cw-1 d co fl ** hä -e’ c | Tl I-h 1 *? TÎ I H H U *> 35 | hEchss h ^ · h h i g η ® o c

® -rH 0 >> - ri 0> .. 1 «" 0 I H S O -M

»M -pOI-UOtHOH X Ο I * III H

- S U-C * 3 U-5 * 3UU φ h4 * J = Ό CMA z a -a i at i œ λ h a ti i ° ι ι i u = 2 i * c i >> fi «·» h ^. o ► »dh oos e Ä ~ +> ÄH häh H-Ä-ίΙ H4 9 * SU-rja ^ î_, cs bï UclN S. ί * U4H H -H T3 N £ ~„ ouavuaaua>, w «« E> > <a · r T* -μ -P *H -μ -μ Ή -P -P · Q ** Γ J |OUlO^I startH, J kindb ·, .7 vT ca+j+jr> - jw c- \ +> ^ 4 «λ -m -U> -5 * Ό +> a ko>, · J" 45 ~ / Board: Or. Horboit Aemis Or. Christian Sruhn Hans-Jàrgeri Hamann Poatanadrtft: SCHEfliNÛ A < 3D-1000 Bmrlfn Λί <^ oadea * Ä0311

- / Z from right Heinz HannseKarl Ono Mitteistenscïieid Or. Horst Witzai PestsMX * Account: Bwlfn-Weet 1175-m. Γι ίιΠτ ^ η imimiO

· Chairman of the Au / sicmsracs: Or. Cduard v. Expectations in Berlin Commeni> e «* ΛΟ. Oertln. Account Mr. USTBOiM. MnCMtzaM ICQ 400 i Sia der Geeellsccett: Semn and Get * · ** »+ ** * &. ^ In. ton «o ^ ._ Zel / ao * ._ B« ld..tzww 100 7® 00 j Handelaragisier: AG Ciiariottenourg 33 ΗΒΘ 233 u. AG Kamen HRS0061 vaxatn "** B *" * B * ri "*

A · A / A

Claims (6)

1. R5 '^ 4— R3 11 R4 4 15 or their metal compounds with compounds of the general formula: R2 - X III ,. i ’20 4 if appropriate in the presence of acid-binding agents’ 1 and in the presence of a catalyst ί or I i 2. b) compounds of the general formula I H0N I ’\! NiH! - 30 üt ^ \ - Η XV; «5 r4 either with compounds of general formula 4! 35 0 ORg V || ^ 0 or - if R ^ represents a - C ^ -alkoxycarbonylmethylrest I, - with compounds of general formula 1 ’f-" 4 "] j Board of Directors: Dr. Herbert Asmis - Df. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AGD-1000 Berlin KPoatfadl MM11 I 11 Dr. Hainz Hann * - Karl Otto Mtttelstensdieid - Dr. Horst jokes! Postsehe <* - account: Bertin-West 1175-HH. BanWateafW KBMQW I - Chairman of the Supervisory Board: Dr. Edward v. Sdiwartzkoppen Berliner Commerzbank AG, Berlin, account no. 108709 * 00, Banldett2aM 1004086 I | Company headquarters: Berlin and Bergkamen 1®!, '! "** ^ 51 * ° ίη ·, 0ί? * ΗΙ5.Α5 · K <î! Ît <iNrn! I3 ^ a * QfrtÎU * tn" W 10078000 3 - δ Commercial register: AG Charlottenburg 93 HHB 283 u. AG Kamen HRB 0061 5 * ri '"/,, lflîrS! Urt ^ B ·" ““ · BoHm, t il * Account no. 14-382. BanUeitzahl 300 20200 ί ι SCHERING AG -h- Commercial ·? Legal protection 1.Triazinones of the general formula N Rτ-fO .- (λ Tf j - *, rÀçHçJ- * 3 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichloro'-20 phenyl, 4-fluorophenyl, 4-trifluonomethylphenyl, 2-thienyl, 2,5-dichloro-3-thienyl, isopropyl, sec-butyl, tert-butyl, chloro-tert-butyl, 2-hydroxy-l, 1-dimethylethyl, methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, cyclopropyl, cyclopentyl or cyclohexyl, R ^ methyl, ethyl, propyl, allyl or Propargyl, ity and Ä5 each mean “Vmsairrntott” the ** tbyl at “n 0 or 1. _________ - -. 3. 3-tert-Butyl-8-propargyl-4,6,7iS-tetrebydrei * ideeo / 2,1-ç7- / Î, 2,47-trxazin-4-one. - 30 ^ 3-tert-butyl-9-methyl-6,7, ô, 9-tetrmhydro-4H-pyrinï- w dino / 2 ”, l-c7 / X, 2,47triazin-4-one. 5. 3 ~ Öyc iohexyl- 8-me thy 1 - 4 ^ * 6.7 »” 5 ~ ~ fce trahydro imidazo- / 2, l-c7- / l, 2,47-triazin-4-one. _ - ..... .... | 35 6 * 3-tert'Buty1-6i7), 8-dimethyl-4,6,7,8-tetrahydroinidazo- / 2, l-c7- / î, 2,47-triazin-4-one. ___ 7. 3-tert-Butyl-8-methyl-4,6,7,8-1etrahydroimidazo- / 2, l-ç7- / ï, 2,47 ~ triazin-4-one 40. <^ Board: Dr. Herbert Aamis - Dr. Christian Bruhn - Hans-Jürgen Hamann Postal address: SCHERING AG - 0 * 1000 Berlin 05Poetfecfi 650311 Z Dr. Heinz Hannes Karl Otto MitteistensctiaidDr. Horst Witzei Postsefiedc account: Berlin-West 1175-101. Bankieitz 10010010 £ Chairman of the Board: Or. Eduard v. Schwartzkoppen Berlin Commerzbank AG. Berlin, account no. 108 700800. BankleitzaM 10040000 I Registered office: Berlin and Bergkamen Berliner Disconto-Bank AG. Berlin. Account number. 241/5000. Bank sorting name 10070000 *. . . »A A.? ._______ ..... .AA Berllnos UanHAtoJtaeallasK · "C" .U..A .. a..lr Du4Ia SCHERING AG -3- Commercial legal protection S ^ 8. Process for the production of triaxinones according to Claims 1 to 7, characterized in that a) Compounds of the general formula i ° = CXI, - H 2. triazinones according to claim 1, wherein R is phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 5 R7OOC -CSC- COOR7 VI if appropriate in the presence of bases or 9 c) compounds of the general formula YR * j 1 * - R_ * R- - 1 1 VII "5 ycar ^ R, ι n 3rd 15 rit with compounds of the general formula 20 R, N - NH 2 vin o <5 ^ or d) compounds of the general formula; 30 v 0 = LJl * N - B2 IX H j with compounds of the general formula c 35 XX R- - "(CH'J - R- XP ι n J * h hO /” 5 "/ J Chairman: Dr. Herbert Asmia Christian Bruhn - Hans-Jürgen Hamann Postal address: SCHERING AG D-1000 Berlin 06 · Postfach (50311 «z Dr. Heinz Hannse · Karl Otto Mittelstenscbeid. Dr. Horst Witzei Postsdieck-Komo: Berlin-West 1175-101, Banfcleitzahl 10010010 S Chairman of the Supervisory Board: Dr. Eduard v. Scftwartzkoppen Berliner Commerzbank AG, Berlin, account no. 10β 7DM 00. Bank code 100 400 00 - I registered office of the company: Berlin and Bergkamen | «J100 ™ ® S Commercial register: AG Charlottenburg S3 HRB 2S3 and AG Kamen HBB0061 ^ 'I SCHERINGAG 1 ~ 3 ~ Industrial property protection 11 · or e) compounds of the general formula V with compounds of the general formula h2n HN-R R5' ^ <CH) JR XI * 10 I n 3. ; 1 f | 9 and the connection 1. i H0NNH - ^^ - SCH. XII 15 2 3 in the presence of bases in which R ^, Rg "R ^" R,, R and n have the meaning given above, χ "in, halo ** 5: r genatom, a sulfate or a Toayl group ·, Y is an oxygen or sulfur atom, Rc hydrogen, a methyl or ethyl-20 ö re st and R ^ a C ^ -C ^ alkyl radicals share it. ----- 9. Agent with selective herbicidal activity, characterized by a content of at least one compound according to claims 1 to 7. 10. Agent with selective herbicidal action according to claim 9 in a mixture with carriers and / or auxiliaries. ! 30 ........ V i! 35, -6- σ »en i: Board of Directors: Dr. Herbert Asmis - Dr. Christian Bruhn - Hans-Jürgen Hamann Postal address: SCHERING AQD-1000 Bariin 65Postbox KOS 11 - z Or. Heinz Hannse - Karl Otto MittelstenscheidDr. Horst Witzei postal check account: Berlin-West 1175-101, Bankleltzehl 100 10010 | Chairman of the Supervisory Board: Or Eduard v.SchwartzKopp.n Ber.inar kÄ 5 hand «lar * çiat * r: AG Ctiarlonwiourg S3HR8 2B3 u. AG Kamin HRS006) B ^ nn— · Handaw-Oaaarlacnan - FranWurer Ban * -, Bariln, u. Account number. 14-302. BaflkfaitxaM 1003B00 toxitr «! 1 SCHERING AG GomfeticW RvcMsccfauts 0 methyI.orrv. ·> - "süb" tin: iert aromatic "or aromatic- .1.1 in! \? R.isc · ien carbohydrate residue, R", R. and R_ are pale or different and each contain vapors, one optionally C 1 -C 6 alkyl group substituted one or more times by halogen, a given one or more, if identical or different, by C 1 -C 6 alkyl, halogen, C 1 -C 4 alkoxy, the nitro group and / * or the Trifluoromethyl group substituted aryl radical i »and n mean 0 or 1 ,. and their salts with inorganic ^ and organic acids. 5 K 15 in the R 1 is hydrogen, “inan optionally substituted with halo and / or cyanide, or hydroxyl and / or C 1 -C 4 -alkexy, a C 1 -C 6 -alkyl radical optionally one or more times by alkyl and / or Halogen and / 2o or phenyl substituted C ^ -Cg-cycloalkyl radical, «in C ^ -C ^ alkoxycarbonylmethyl, one optionally or one or more times by C ^ -C ^ alkyl and / or halogen and / or C ^ -C ^ -Alkoxy and / or the nitro group and / or the trifluoromethyl group substituted aromatic 23 or aromatic-aliphatic hydrocarbon radical or a heterocyclic carbon waaf crateoff, Rg hydrogen, one optionally one or more times by halogen, C ^ C ^ alkoxAl, cyan, C ^ C ^ -Alkylthio 30 and / or hydroxy substituted C ^ -Cg-alkyl, C ^ -Cg-alkenyl, C ^ -Cg-alkynyl, C3-Cg-cycloalkyl or cycloalkenyl, optionally one or more times by oxygen, sulfur or nitrogen interrupted C ^ -Cg-alkyl residues Cj-C ^ -alkoxycarbonyl.-35 C ^ -C ^ -alkyl, a given if necessary, one or more halogen-substituted C 1 -C 6 -alkylsulfonyl groups, or one or more, optionally one or more, identical or different from C 1 -C 6 -alkyl, halogen, CC, alkoxy, the nitro group and / or the trifluoro-1 4 gk ° -2- / »/ - \ Board of Directors: Or. Herbert Asmis - Or. Christian Sruhn · Hans-Jürgsn Hamann Poatanadirtft: 3CHERIMQ AG · 0-1008Barth« as. ftjHaü> agile - - / \ Vr. Heinz Hanna · - Karl Otto Mitte <snnsai..d - Or. Horst Witz * Postachedt account: Bvtln-Wat 1175-101. 1001001! «I Chairman <3 · * Supervisory Board: Or. Sduard v. ScnwertzKogpen Berliner GartimmamcAG fwiin. Knam in · ine-annem i ^ firiettT ^ d 1f tim '/ g Registered office at Gaiallsdiatt: Berlin and Bargxamen Bwlnw 0lsedfl »o-8anitAG. Berlin. Account Wr. Μ1ΛΠΜ. BanftMOaM 10170000 5 PATENT CLAIMS 6 Registered office of the company: B ^ lm and Bergamen "ne" * "Berliner Handels-Gesellschaft - Frankfurter Bank -, Berlin, o Commercial register: AG Charlottenburg 93 HRB 283 u. AG Kamen HRB 0061 Account no. 14-362, Bankieitz number 100 202 00