NL8400013A - TRIAZINONES, PROCESS FOR THE PREPARATION OF THESE COMPOUNDS, AND METHODS CONTAINING THESE COMPOUNDS WITH SELECTIVE ACTION AS HERBICIDE. - Google Patents

Description

* *. * * VO 5305

Title: Triazinones, process for the preparation of these compounds, as well as agents containing these compounds with selective herbicidal activity.

The invention relates to new triazinones, to a process for the preparation of these compounds, and to agents containing these compounds with selective herbicidal activity.

It is already known that 1,2, h-triazine-5-one derivatives, such as for example U-amino-6-tert-butyl-k, 5-dihydro-3-methylthio-1,2, U -triazine-5-one (Belgian patent 69T083-J as a weed killer can be used. However, the problem of a good effect as a herbicide against problem weeds while simultaneously good tolerability against various main crops is not solved by these herbicides.

The object of the present invention is the development of an agent which can be used in various main agricultural cultures against difficult to control weeds without damaging them. This problem is solved according to the invention by an agent containing ala new active compounds at least one triazinone of the general formula 1, in which: hydrogen, optionally by halogen and / or cyano and / or hydroxyl and / or C 1- C 1 -alkoxy substituted C 1 -C 8 -alkyl radical, an optionally mono-20 or polyalkyl and / or halogen and / or phenyl-substituted C 1 -C 8 -cycloalkyl radical, an -C 1 -alkoxycarbonylmethyl, optionally single or multiple aromatic or aromatic-aliphatic hydrocarbon radical substituted by C 1 -C 2 -alkyl and / or halogen and / or C 1 -C 2 -alkoxy and / or a nitro group and / or a trifluoromethyl group; hydrogen, optionally singly or multiply substituted by halogen, C 1 -C 2 -alkoxy, cyano, C 1 -C 2 -alkylkio and / or hydroxyl-substituted C 1 -C 6 alkyl, C 8 -C 8 alkenyl, C 1 -C 6 alkyl C 4 -alkynyl, C 5 -C 8 cycloalkyl or cycloalkenyl, an optionally interrupted C 1 -C 8 alkyl residue, singly or multiply interrupted by oxygen, sulfur or nitrogen, a C 1 -C 2 -alkoxycarbonyl-C-C -alkyl, an optionally singly or multiply halogen-substituted C 1 -C 6 -alkyl-sulfonyl group or an optionally single or multiple, mutually identical or 84 0 0 0 1 3 - 2 - different by C -C ^ - alkyl, halogen, C 1 -C 2 -alkoxy, a nitro group and / or a trifluoromethyl group, represents substituted aromatic or aromatic-aliphatic hydrocarbon radical, R 2, and are the same or different from each other and each hydrogen, possibly a single or polyhalo-substituted C 1 -C 6 -alkyl group, optionally single or multiple, mutually identical or different by C 1 -C 6 -alkyl, halogen, C 1 -C 6 -alkoxy, a nitro group e n / or a trifluoromethyl group represents a substituted aryl radical and n is 0 or 1, and its salts with inorganic and organic acids.

As inorganic and organic acids for the formation of acid addition salts, mention can be made, for example, of the halogen acids, such as, for example, hydrochloric acid and hydrobromic acid, furthermore phosphoric acid, sulfuric acid, in particular nitric acid, mono and bifunctional carboxylic acids and hydroxycarboxylic acids such as, for example, acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid, as well as sulfonic acids, such as, for example, p-toluene sulfonic acid and 5,5-naphthalenedisulfonic acid.

These acid addition salts can be obtained by conventional salt formation-2Q processes, for example, by dissolving a compound of formula J in a suitable solvent and adding the acid,

The compounds according to the invention are surprisingly excellent for controlling problematic weeds at a tolerance, especially for soybeans, potatoes, cotton, corn, wheat, barley and rice. They exceed the known means in this respect. A great technical advance is associated with these properties.

Eat is known, that. from an economic point of view, the main agricultural cultures in terms of bearing fruit are more and more adjusted in a close-together relationship. With regard to the weed flora, this has the result that more and more specific beginner growth floras develop. When below that, which is almost the rule, occurs. weeds which are difficult to control in the field of weed control with the current state of the art, conditions arise which easily lead to the dominance of such species.

8400013 ♦ * - 3 -

For example, efforts are being made to address this problem by attempting to control it with ample 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 follow-up culture 5 via the soil, this often also causes damage. Thus, a progressive herbicide is desired to have good activity against problem weeds while at the same time having good tolerance against several main agricultural cultures which succeed each other in freezing.

The compounds according to the invention meet these requirements and are distinguished by a surprisingly good compatibility with the above cultures, where they can be used both before and after emergence.

Its action as a herbicide extends against many weeds.

Highly controllable problem weeds are Abutilon theophrastii, Ipo-moea ssp ,, Solanum ssp., Viola ssp., Echinocflloa crus galli, Setaria ssp., Digitaria asp., Brassicia kaber, Cassia, Sesbania, Datura.

The application can be done by processing in the Soil before sowing the culture, or before the emergence or after the emergence.

The amounts to be used for selective weed control are about 0.1-5 kg of active compound / ha. With larger amounts to be used, the compounds can also be used for total weed control.

The compounds according to the invention are distinguished by an optimum action of the kind described in Particularly the representatives, wherein in the general formula 1 R 1 phenyl, 2-methylphenyl, 3-methylphenyl, U-methylphenyl, 2- chlorophenyl, 3-chlorophenyl, U-chlorophenyl, 2, IJ-di-chlorophenyl, 1-fluorophenyl, k-trifluoromethylphenyl, 2-thienyl, 2,5-dichloro-3-thienyl, isopropyl, sec-butyl, tert-butyl, chloro-tert-butyl, 3Q 2 -hydroxy, 1,1-dimethylethyl, methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, cyclopropyl, cyclopentyl or cycloheoyl; R 1 methyl, ethyl, propyl, allyl or propargyl; R ^ and R ^ each represent hydrogen or methyl and n is 0 or 1.

The compounds of the invention can be used either alone or mixed with one another or mixed with other active compounds. Defoliating agents, plant protection agents, 8400013 y S '- k - parts or agents for controlling harmful organisms can be added, depending on the desired purpose.

If a broadening of the action spectrum is envisaged, other biocides can also be added. For example, as the herbicidal mixed-5 components, those active compounds are suitable which are listed in "Weed Abstracts," Volume 31, Number J, 1982, under the heading, "List of Common Names and Abbreviations employd for currently used. Herbicides, an Plant groth Regulators "in" Weed Abstracts ".

The active compounds according to the invention or a mixture thereof can advantageously be used in the form of preparations, such as; powders, litters, granulates, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers, respectively, diluents and optionally of wetting, bonding, emulsifying and / or dispersing agents, preferably in the form of emulsion concentrates.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as, for example, toluene, xylene, ketones, such as, for example, cyclohexanone, isophorone, sulfoxides, such as dimethyl sulfoxide, carbonic acid amides, such as, for example, dimethylformamide, furthermore fractions. of mineral oils. Suitable solid carriers are mineral earths, for example bentonite, rock egg, talc, kaolin, attapulphite, limestone, silicic acid and vegetable products, for example flours.

As surface active compounds, mention may be made, for example, of calcium lignin sulfonate, polyoxyethylene alkyl phenol ethers, naphthalene sulfonic acids and their salts, phenol sulfonic acids and their salts, formaldehyde condensation products, fatty alcohol sulfates, and substituted benzene sulfonic acids and their salts.

The content of active compound (and I in the different preparations can vary within limits. For example, the agents contain about 5-25% active compounds, about 25-5% by weight of liquid or solid carriers. as well as optionally at most 20% by weight of surface acetate materials.

The application of the agents can take place in the usual manner, for example, with water as a carrier, in amounts to be sprayed of approximately HO.O.-1 QO.Q lit er / ha. The use of agents according to the so-called low-volume and ultra-low-volume methods is just as possible as 8400013-5 as their use in the form of so-called micro-granulates.

The compounds of the general formula I according to the invention can be prepared using a method known for analogous compounds.

The compounds according to the invention of the general formula 1 can be prepared, for example, in the manner described in claim 3.

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

The reaction components are reacted according to the process variants a-d between Q ° and T20 ° C, but generally between ambient temperature and the reflux temperature of the respective reaction mixture.

The reaction time is usually 1-72 hours.

The reactants are used in approximately equimolar amounts to synthesize the compounds of the invention. Suitable reaction media are solvents which are inert with respect to the reactants. The choice of the solvents or suspending agents depends on the use of the respective starting compounds and the acid acceptors or bases used. As solvents or suspending agents can be mentioned, for example, ethers such as diisopropyl ether, tetrahydrofuran and dioxaaa, aromatic hydrocarbons such as toluene and xylene, carbonic nitriles such as acetonitrile, carboxylic acid amides such as dimethyl formamide and alcohols such as methanol, ethanol, propanol, isopropanol and t -butanol.

Suitable acid acceptors are organic bases, such as, for example, triethylamine, li, dimethylaniline and pyridine bases or inorganic bases, such as oxides, hydroxides and carbonates of the alkaline earth and alkali metals.

30. Liquid bases, such as pyridine, can be used simultaneously as a solvent.

The methods for the synthesis of the compounds according to the invention according to the method variant (any metal compounds, if required), can be prepared, for example, by reacting the compounds of the general formula II with metal compounds of the general formula MZ, ♦ 8400013-6 - optionally using of a solvent, wherein M represents a monovalent with eel equivalent, preferably a sodium, potassium or lithium atom, and Z represents hydrogen, hydroxyl, lower alkyl, alkoxy or an amino group, preferably hydrogen.

The reaction of the eel-free compounds of the general formula 2 optionally takes place in a two-phase system, consisting of a triazinone of the general formula 2, which is dissolved in an inert solvent, an alkali metal hydroxide, in solid state or as a solution in water, and a catalyst. Suitable catalysts are onium compounds, such as quaternary ammonium, phosphonium and arsonium compounds, as well as sulfonium compounds.

Also suitable are polyglycol ethers, in particular cyclic, such as, for example, 18-crown-6 ”, and tertiary amines, such as, for example, tri-butylamine. The mixing ratios of the reaction components can be varied within wide limits. The reactions are preferably carried out with a 1 to 10-fold excess of R 1 -X and a 1 to 10-fold excess of hydroxide. Of the catalyst, 0.02 equivalent is sufficient.

The conversion takes place between 20 and 10 ° C, generally however between 20 and 6 ° C. The reaction time is 1 - 72 hours. During the total response time is? requires a good mix,

The compounds of the invention prepared according to the above process can be isolated from the reaction mixture by conventional methods, for example, by distilling off the solvent used at normal or reduced pressure, or by precipitation with water.

If desired, a separation of the isomer mixtures can take place by crystallization or column chromatography, as these are generally formed according to the process variants a1 and d1.

The compounds of the invention are generally colorless and odorless crystalline bodies, which are sparingly soluble in water and - aliphatic hydrocarbons, are moderately to readily soluble in halogenated hydrocarbons, such as chloroform and ketones, such as acetone, car -Honic acid amides, such as dimethylformamide, sulfoxides, such as dimethylsulfoxide, carbon dioxide, such as acetonitrile and lower alcohols, such as methanol and ethanol.

Particularly suitable as recrystallizing solvents are 8400013-7-7 "ethanol, isopropanol, diisopropyl ether, toluene, acetonitrile and ethyl acetate.

The following examples further illustrate the preparation of the compounds of the invention.

5

Example I.

3-tert-3-butyl-8-propargyl-1, 6,1,8-betrahydroimidazof2,1-I [1,2, k] triazine-U-one.

In a solution of 9.7 g (0.05 mol) 3-tert-butyl-6,7,3-tetrahy-10-droimidazo [2,1-c] [1,2 k] -triazine-1 1.5 g of 80% sodium hydride (0.05 mol) was added at ambient temperature with stirring in 150 ml of dimethyl 1 formaznide. After 15 minutes, 5.95 g (0.05 mol) of propargyl bromide was added dropwise, stirred at 25-30 ° C for 1 hour and the reaction mixture was placed in 1 liter of ice water. Then it was extracted twice with 150 ml of chloroform each time, dried with magnesium sulphate and evaporated to dryness. The residue was recrystallized from isopropyl ether.

Yield: 7.71 g = 66.5% of theory melting point: 89H30 ° C analysis; c I N

20 calculated; $ 2.05% 6, gk% 2kt '\ 2% found: 62.15 $ 6.88 $ 21.27 $

Example II.

8- [Methyl] 3- (3-methylphenyl 1-h; 6,7,8-tetrahydroimidazo [2,1-k]] [1,2, M-trlazi-25-ne-rl-one.

In a solution of 0.56 g (0.02 moll 3 - (3 --- methylphenyl 1-1,6,7,3-tetrahydroimi; dazol2,1-c] [1,2 U] trilazine 1 -one in 6 ml of dimethylformamide was stirred at ambient temperature 0.6 g of 8% sodium hydroxide.

(Q.02 mol I charged.

3Q After 15 minutes, 2.8U g (Q, G2 rnoll of methyl iodide was added dropwise and stirred for an additional 1 hour at ambient temperature. The reaction mixture was then placed in 1 liter of ice water, extracted twice with 150 ml of chloroform each time and the organic phase dried with magnesium sulfate. After removal of the solvent, the residue was recrystallized from ethanol.

35 Yield; 1.2 ^ g = * 25.6 $ of the theory

melting point: 17 ^ 175 ° C

8400013 • 8 - analysis: c H yy calculated: 6k, bk% 5.82 $ 23.13% found: 6U, Q9 $ 5.93! 22.90% EXAMPLE III, 3-Methoxycarbonylmethyl-1,6,7,8-tetrahydroimidazo [2,1-c] [1,2,1-1-triazin-yonone.

An amount of 39.7 µg (0.28 mol) of acetylene dicarboxylic acid dimethyl ester was added with 65.3 g (0.286 * mol). 2-hydrazinoimidazoline hydroiodide 10 and 28.5 ml triethylamine in UC 50 ml methanol stirred for 2 hours. The precipitate was filtered off with suction, washed with isopropyl ether and dried under reduced pressure.

Yield: 26 *, ^ 5 g = ^ 5 $ when the theory melting point: 1 $ fW \ 92 ° C (decomposition7 15 analysis: c H

calculated: U5.7l $ k, ÜQ% 26.66% found: i + 5.53 $ * ^, 81 $ '26.53% *

Example IV.

8-Ethyl-3-phenyl-1,6 *, 7,8-tetrahydroimidazof 2,1-c-fl, 2, k-trlazine-U-one.

To a solution of 2k, k6 g (0.096 mole) of 3-methyl-2-hydrazinoimidazoline hydroiodide and .17.8 g (0.1 mole of phenylglyoxylic acid ethyl ester in 150 ml of ethanol) was added 50 ml of a 2-molar HaOEt solution, then refluxed for 1 hour, the alcohol was distilled off and 1 * 50 ml of HgQ was added to the residue, after which it was extracted twice with 150 ml of CHCl 2 each time. and the organic phase was dried with MgSO 4. After removing the solvent, it was recrystallized from isopropanol,

Yield: 3 g = .13% of theory. Melting point: .151 - J 52 ° C

analysis? calculated: C 6k, bk% E 5.82 $ ff 23.13 $ 'found: C 6k,'. 10 $ H 5.97 $ ff 23.11 $ 'Predefined V.

1.78 g (CL, 0.01 mole of phenylglyoxylic acid ethyl ester and then 5 ml of ethylenediamine 840 013-3-3 ~) were added to 1.22 g (Q, 0 .mu.m of diethiocarbazic acid methyl ester).

added. It was then boiled for 15 minutes, and after cooling, 50 ml of ^. ^ 0 were added and extracted with CHCl. The organic phase was dried with MgSO4 and the crude product thus obtained recrystallized from EtQH. Yield: Q, kJ g = 22% of theory 5 melting point: 218-219 ° C

analysis: calculated: C 6ΐ, β7 * H ^, 71 # N 26, \ 6% found: C 6l, 60% H 99% $ 26, -kï%

In an analogous manner, the compounds listed in the following table could be prepared using corresponding starting materials.

Example Name of the connection Physical constant

VI 8-Methyl-3-phenyl-k, 6, 7,8-tetrahydroimidazo. M.p .: -1 ° C

15 [2,1-c] [11] J-triazine-iv-one.

VII 3— (3- ^ ethylphenyl-4,,, 7.8 ~ tetrahydroimidazo - mp: 198 ° C

[2,1-c] [1,2, ii] triazine -onone.

VIII '3 "(2'-Ethylphenyl 1-4,' ', 7, δ-tetrahydroiaaidarr ·. M.p .: 223 ° C

zo [2,1-c] {1,2,3-triazin-4-one.

20 IX 3-enyl-8-propargyl7 »8-tetrahydroimi— Mp .: 15 ° C

dazo [2,1-c] [1,2, U] vtriazine-4-one.

X 8-Methylsulfonyl-3-phenyl-4, 7,8-rtetrahy— Mp: 259 ° C

droimidazo [2,1-c] [1,2, U] -triazine4 * -one._

XI 8-Methyl-3-ftsrt-butyl-4, 7,8-tetrahydro-mp: 129 ° C

Imidazof2, J-o] [1,2, U] -triazine4 + one.

XII 3- ^ or-Butyl43-methylsulfonyl-4,7,7 ^ -4: 6 -, mp: 215-216 ° C

trahydroimidazole 2j 1-c] [1.2? U] -triazine-4-οη.,

XIII .3- * tert-Butyl- ^ 8- * propargyl-4i6'J7J8-rtetrahy- Mp: 89-90 ° C

droimidazo [2,1-rc] [1,2, li] -Ariazine - 2 - one.

30 XIV 3- ^ Phenyl-4,6 ", 7,8-tetrahydroimidazo [2, -1-c] ^ m.p .: 22Q ° C

[1, 3, 3-triazin-1-one.

XV S-tert-Butyl- ^ jeIss-ftetrahydroimidazo- Mp .: 2l + 5 ° C

[2,1-ro] [1,2, U] -triazine-4-one.

XVI 8-Chloromethylstilphonyl-3-phenyl-4, 7, 5, 3-fc and ~ m.p. : 222 ° G (dec. 35 trahydroimidazo [2, T-c] [1,2] -J-triazine-2-one.

84 0 0 0 1 3 0

Example. Kaam Tan the connection Physical constant - 10 -

XVII 8-Allyl-3-phenyl - ^, 6,7,8-tetrahydroimidazo- Mp: 138 ° C

[2,1-c] [1,2, U] -triazine-4-one.

5 XVIII 3 - (^ - Fluorophenyl) "- 45 ^, 7,8-tetrahydroimida- Mp: 252 ° C

zo [2,1-c] [1,2,6] triazine-ii-one.

XIX S - ^ - Butenyli-S-phenyl- ^ ji ^ jS-tetrahydro- Mp: 85 ° C

imidazo [2,1-c] [1,2,3] triazine-4-one.

XX 3 - = - (2,5-Dichloro-3-thienyl 1-4-, 6.7 s8-tstra- Mp .: 23 ° C

Hydroimidazo [2,1-c] [1,2,2] triazine4-one.

XXI 8-Meth02ymethyl-3-phenyl4-, 6,7,8-tetrahy- Mp: 151 ° C

droimidazo [2,1-c] [1,2,1 +] triazinone.

XXII S-i'enyl-^ ^ j8,2 "tetrahydro-4K-pyrimidino- Mp: ^ 280 ° C

{2,1-c] [1,2,6] triazine-4-one.

15 XXIII S-Cyanomethyl-S '-' phenyl- ^ '-' tetrahydro- Mp: 258 ° C

imidazo [2,1-c] [], 2,1 +] -t riazine-it-on.

XXIV 2- (2-Butenyl-3-phenyl-1, 7 ', 8,9-tetrahydro-mp: 108 ° C

UK-pyrimidino [2,1-c] [1, 2, H] -uriaz ine-4-one.

XXV 8-Allyl-3-tert-hutyl-4,6,7,8-tetrahydro-oil. .

Imidazo [2,1-c] 1,2,2] triazine-k-one.

XXVI 8— (2-Methyl-allyl) _-3-phenyl-6,7,8,9-tetra— Mp: 12 ° C

hydroimidazo [2,1-c] [1,2,1j] -t riazine-4-one.

XXVII 3-enyl-242-propenyl-6,7,8,9-tetrahydro - mp: 106 ° C

UE-pyrimidino [2.1 -o] [1,2, H] -triazine - ^ - on ..

25 XXVIII 34 ^ -Tiorphenyl) 43 - = - methyl 4-, 6,7> 8-tetrahydrom.p. : 191 -192 ° C

droimidazo [2,1-c] [1,2, U] -triazine4-on,

XXIX 344rFluorophenyl) -8-propargyl-Y-, 6,7,8-m.p .: 17J ° C

trahydroimidazo {2,1-o] 11,2,3-triazine-4-ron,

XXX 3 '= - (3-Methylphenyll-8-propargyl4-, 6,758 - mp: 175 ° C

3Q trahydroimidazo [2,1-c] [1,2,2] triazine-1 + -one.

XXXI 3-Metho: sycarbony] methyl-1,6,7,8-tetrahydro— Sm.p. : 192 ° C

imidazo [2,1-c] [1,2,6] triazine-4-one.

XXXII 8-Methyl-3- (3 - = - methylphenylI4-, 6,7,3-tetrahy- Mp: 175 ° C

droimi'dazo [2,1-c] [1,2] i-triazine-Xi-one.

35 XXXIII 8-EthoxycarDonylmethyl-3-phenyl4-, 6,7,8-Tp: 136 ° C

trahydroimidazo [2,1-c] [1,2,1] triazine-U-one.

84 0 Ö 0 1 3

Example Connection name Physical constant - 11 -

XXXIV 3-tert-Butyl-S-methyl-1,2,8,9-tetrahydro- ". Sm. p .: 138-1 40 ° C

UH-pyrimidino [2,1-c] [1,2,4] triazin-4-one.

5 XXXV 3-Phenyl-8 (li- (3,6,9-trioctadecyl) -1,4,6,7- Oil (8} -tetrahydroimidazo [2,1-c] [1,2,4] -tria -zine-4-on.

XXXVI 3-tert-Butyl-3-trifluoromethylsulfonyl- Mp: 174 ° C

4,6,7,8-tetrahydroimidazo [2,1-c] [1,2,4] -10 triazin-4-one.

XXXVII 3-Phenyl-9 - (2-propynyl-1, 7,8,9-tetrahydro- Mp: 140-141 ° C

4E-pyrimidino [2,1-c] [1,2,43-triazin-4-one.

XXXVIII 3-tert-Butyl-9- (2-propynyl-J-6,7,3,9-tstra- Mp: 134-135 ° C

hydro-4ff-pyrimidino [2,1-c] [1,2,4] -triazine-4-0n,

XXXIX 3 — Isopropyl-4,6 ”, 7,8-t etrahydroimidazo— Mp: 227 ° C

[2,1-c] [1,2,4] triazin-4-one.

XL 3-Cyclophthyl-4,6 ", 7,8-tetrahydroimiG.azc— Mp: 239 ° C

[2.1 - 11.2,4] triazine - 4-one.

20 XLI 3-IsoButyl-4,6 ', 7,8-tetrahydroimidazo— Mp .: 187 ° C

[2,1-c] [1,2,4] -triaz ± ne-4-one.

XLII 3-r- (2-Tbienyl 1-4, o, 7.8-t etrahydro imidaz o - mp: 260-262 ° C

[2,1-rc] [1,2,43-tr £ az £ ne-4-on «

XIIII 8-Cyano - ^ (7l-metSyl-3-phenyl-r4,1,7,8-rt-mp: 235 ~ 237 ° C

Trahydroiaidazo [2.1 -c] [1,2,4] -tr-azine- 4τοη.

XLIV 3-Isopropyl-8-rmetayl-4,6 ", 7,3-tetraphydro— Mp: 68 ° C

imidazo [2, J-c] [1,2,43-rtr £ az £ ne-4-on,

XLV 9- «methyl-3-phenyl-6”, 7,3,9-tetrahydro-4 H-mp: 133-185 ° C

30 pyrim £ dino [1,2-c] [1,2,4] -tr £ azine-4-one,

XLVI 3-Oyclohexyi-5-metayl-3 ", 7,3,9-tetrahydro— Mp: 143-144 ° C

imidaso] 1,2-c] [1,2,43-triazone-4-one.

XLVII 3-Cyclohexyl-8-propargyl-4,6,7,8-tetra-> Sm.p .; 142 ° C

hydroimidazof 1,2-c] [1,2,4] triazin-4-one.

. 35 XL7III 3-Cyclohexyl ^ 3-methyl-4,6,7,8-tetrahydro— Mp: 115 ° C

imidazo [2,1-c] [1,2,4] triazine-4-one.

8400013

Example Connection name Physical constant - 12 -

XLIX 3-Is.opropyl-8-propargyl-1 +, 6,7,8-tetrahydro- Mp: 73 ° C

imidazo [2,1-c] [1,2,1 +] triazine-1 + -one.

5 L 8-Allyl-3-risobutyl-l +, 6,7,8-tetrahydroimida ~ Mp: Ö5 ° C

zo [2.1 -c] [1.2, 1; ] -triazine-1; -one.

LI 9-Allyl -3-tert-butyl-6,7,8,9-tetrahydroimi- Mp: 116 ° C

dazo [2,1-c] [1,2,1 +] triazine-1 | -one.

Lil 3 ~ tert-Butyl-6 (7l., 8-dimethyl-1 +, 6,7,8-tetra- mp: 127 ° C

1o hydroimidazo [2,1-c] [1,2, 1+] triazine-1 + one.

LUI 8-Cyclohe: xyl-3 ^ phenyl-1 +, 6,7,8-tetrahydroimi- Mp: 15h ° C

dazo [2,1-c] [1,2,1+] triazine-1-one.

LU 3— (2,5- ^ ichloro-3-tftienyl J-8 (1) -methyl- Mp: 163-165 ° C

1+, 6,7,8-etrahydroimidazo] 2,1-c] [1,2, U] -15 triazine-1 + -one.

LV 3- (2,5-Dichloro-3-thienyl) -8-propargyl- Mp: 190-191 ° C

1 +, 6,7,8-tetrahydroimidazo [2,1-c] [1,2,1 +] triazine-1 + -one.

LVI 3-Isobutyl-8-propargyl-1 +, 6,7,8-tetrahydro- Mp: 107 ° C

Imidazo [2,1-c] [1,2,1 +] triazin-1 + -one.

LVII 3-Methyl-1 +, 6,7,8-t etrahydroimidazo [2,1-c] - Mp:> 250 ° C

[1,2.1 +] triazine-1 + -one.

LVIII 3-tert-Butyl-8-methyl-1 +, 6,7,8-tetrahydro- Mp: 186 ° C

[2,1-c] [1,2,1 +] triazine-1 + -one, hydrogen (dec) nitrate.

LIX 3-tert-Butyl-8-chloromethylsulfonyl- Mp: 175 ° C

1 +, 6,7,8-tetrahydroimidazo [2,1-c] [1,2,1+] triazine-1 + -one.

LX 6 (7l, 8-Dimethyl-3-phenyl-1 +, 6,7,8-tetrahydro- mp: 98 ° C

Imidazo [2,1-c] [1,2,1 +] triazin-1 + -one.

LXI 6 (71-Methyl-3-phenyl-8-propargyl-1; 6,7,8-mp: 128 ° C

t etrahydroimidazo [2,1-c] [1,2, 1 +] - triazine- ..... 1 + -one.

LXII 3-tert-Butyl-B-methoxymethyl-1 +, 6,7,8-m.p .: 81 + ° C

Trahydroimidazo [2,1-c] [1,2] +] triazine-1 + -one.

8400013

Example Name of the connection Physical constant - 13 -

LXIII 3-tert-Butyl-8-cyanomethyl-1,6,758-tetrahy- Mp: 100 ° C

droimidazo [2,1-c] [1,2, U] -triazin-4-one.

5 LXIV 8-Methyl-3- (2-thienyl-, 6,7,8-tetrahydro- -Sm.p .: 201 ° C

imidazo (2,1-c] [1,2, U] triazine-li-one.

LXV 3-Isobutyl-8-methyl - 6,7,3-tetrahydroimi- Mp: \ 2k ° C

dazo [2,1-c] [1,2, i +] triazine-1-one.

LXVI 3- (2-Chloro-1,1-dimethylethylJ-4, is7j8-te- Mp .: 20b ° C

Trahydroimidazo [2,1-c] [1,2k] triazine-4-one.

LXVII 8- Allyl-3 "isopropyl-4,6", 7,8 "tetraihydroimi- Sm.p .: oil dazo [2,1-o] [1,2, t] triazin-4-one.

LXVIII 3— (2-Hydroxy-1,1-dimet hylet hy 1J-8-methyl- Mp: 168 ° C

h, 6,7,8-tetrahydroimidazof2,1-c] [1,2, k] -15 triazin-4-one.

IXEX 3- (2-Hydroxy-1,1-dimethylethyl J-8-propar- mp: 103 ° C

gyl-4,6,7,8-tetrafiydroimidazo [2,1-c] - [1,2,6] triazine-4-one.

LXX 3 ^ Hethyi-8-propargyl - ^, 7,8-tetrahydro— Mp: 135 ° C

Imidazo [2,1-c] ph1,2,1] -triazine -on-one.

LXXT 3 - € yclopentyi - ^, 7,8-tetrahydroimidazo— Mp: 218 ° C

12, J ^ c] [1,2,4] -triazine-1-one.

LXXII 3fCyclopentyl-8-methyl-4,1,7j8-tetrahydro - Mp: 121 ° C

imidazof2,1-c] [1,2,6] triazine-A-one.

LXXITI 3-Cyclopentyl-8-propargyl-4J-, 7s8-fcetrahy— Sm.p .; 111 ° C

droimidazof 2,1-k:] [1,2,3] triazine-k-one.

LXEE7 S- ^ lyl ^ -cyclopentyl- ^ ö ^ jS-tetrahydro— Mp: 55 ° C

imidazo [2, J-c] Il2, U] -triazine - 2 - one.

L2XV 3-tert-Butyl-8-rethyl-ri, 6'i7J8-tetraiaydro— Mp: 131 ° C

3Q imidazo [2.1-c] f. 1.2 µU] -triazine-4-one.

LXXYI 3 ^ 3'-enyl-8-ethyl-J; -, 6 ', 7,8-tetrahydroimidazo- Mp: 152 ° C

[2, -1-rc] [J, 2, ^] - trizazin-1-one.

LXXVXI 3- (5-Chloro-2-itaiënyi 1-1, (3,7,8-tetrahydro— Mp: 27Q ° C

imidazo [2,1-fc] [1,2] +] tri'azin-1-one.

35 LXXVIII 3— (5-CHloro-2-taienylI -! - 8-propargyl-1,6,7,3- Mp: 190 ° C

tetrahydroimidazo [2,1-c] [1,2,1] triazine-1-one. 1 8400013 - 1U -

Example Name of the connection Physical constant

LXXIX 8-Allyl-3-methyl-4,6,7,8-tetrahydroimidazo- Mp: 6T-68 ° C

[291 -c] [1-y-triazin-1-one.

5 LXXX 3-tert-Butyl-6,7,8,9-tetrahydro-4-pyrimidi- Mp: 250 ° C

no [2,1-c] [12], 1J -] - triazine - ^ - on. (decomposition)

LXXXI 3-tert-Butyl-8-methyl-U, 6,7,8-tetrahydro- Mp: 250-251 ° C

imidazo [2, T-c] [1,2, +] - triazin-4-one, hydrochloride

10 LXXXII 3- (3, ^ - DimetheEcyphenyl) J +, 6,7,8-Tetrahydro- Mp: 250 ° C

imidazo [2µl-c] [1.2, li-] triazine-U-one

LXXXIII 3- (3, ^ - DimethoQcyphenyli-8-methyl-14-, 6'j7> 8- Mp: 233 ° C

tetrahydroimidazo] 1,2,1-c:] [1,2,] triazine-k-one.

15 LXXXIV 3- (3, U-i-Dimethoxyphenyl) -8-propargyl-4,6,7,8- Sm.p. : 203 ° C

tetrahydroimidazo]; 2,1-c] [1,2, ^] tri'azone (decomposition) one

LXXXV 8 -Allyl — 3— (3,1 + dimethoxyphenylM, 6,7,8- m.p .: 163 ° C

t et r ahydro imi daz o [2,1 -c J [1,2, U] -triazine-20 U-one

LXXXVI 3-tert-Butyl, 6,7j8-tetrahydroimidazo- Mp: 16lit63 C

f2,1-c] (1,2 µl] -friazin-1) -one, dichloroacetate

LXXXVII 3- (3- ethoxyphenyl I-k, 6,7,8-tetrahydroimida, M.p .: 18Q C

Zo {2.1-1c] [1.2, k] -triazine-1 + -one (decomposition).

LTSVIXI 3_ (3'-MethoxyphenylL-8-propargyl-A, 6,7,8-Mp, 175 C

tetrahydroimidazo [2,1-c J [1,2, ^] triazine— (decomposition! U-on

L22XIX 8-Methyl-3- (3-methoxyphenyl 1-b, 6,7,8-t at ra-Sm.p, 177 C

3Q hydroimidaz or 2, J-c] [1,2] +] triazine-1-one

XC 8 (11-Methyl-3- (2-methylsylphenyl) - (11-h, 6.7.8-mp: 110-112 C

tetrahydroimidazole 2,1 -c] [1,2k] triazine-U-one

XQI 3 - (2-methylphenyl-8-propargyl-1 +, 6,7,8-sia.p .: 203 C

Trahydroimidazo [2,1-c] 11,2, Λ] -triazine - ^ - on 8400013

Example Connection name Physical constant - 15 -

XCII 8-AUyl-3- (2-methylphenyl, 6,7,8-tetrahy- m.p .: 173 ° C

droimidazo [2,1-c] [1,2, H] -triazine-U-one

5 XCUI 3- (2-C chlorophenylI-8-propargy1-k, 6,7 »8-t e * - Sm.p: 22k C

trahydroimidazo [2,1-c] [1,2.2] triazine-4-one (decomposition)

XCIV 8-Allyl-3- (2-aethylphenyl-1,6,7) 8-tetrahyd- Mp: 1 ^ 7 C

droimidazo [2,1-c] [1 jS ^ J-triazine - ^ - one, (decomposition) bydronitrate

10 XCV 8 * Allyl * 3- (3-methoxyphenyli-1,6,7, β-t etra- Mp: 77 ° C

hydroimidazo (2,1-cJ [1,2, b] triazine-1-one

XCVI 3-r. (4 * Chlorophenyl-h, 6,1,8-tetrahydroimida - Mp: 211 C

zo [2,1-c] (1,2, U] -triazine-4-one

XCVTI 3 - (^ - Chlorophenyl Γ-8-propargyl-1,6,7,8 ^ fce * m.p .: 18l-l82 ° C

15 - trahydroimidazo [2,1-c] fl, 2,2U-triazine-4-one (decomposition)

XCVIII 8-Allyl-3- (k-chlorophenyl J ~ k, 6,7,8-tetrahy- Mp: 153-155 ° C

droimidazo [2,1-c] [1,2,3] triazine-h-one

XCIX 3 - * (1-Methylcyclo [exyl] -, 6,7,8 '' t6trahydro— Mp: 221 ° C

imidazole 2.1 * o 11.2.] triazin-4-one

20 C 3- (J- »Metfylcyclo & jeayir-8 * propargyl-ri +, ^, 7,8-m.p .: 11 ^ ° C

t et rahydro im daz o [2,1 -c J Γ1,2, kJ — triazine-k-on

CX 8 * Methyl — 3 * (1 * methylcyclonexyl 1-1,6,7,8— Mp: 1Q2 ° C

tatrahydroimidazo [2 y 1-o] [1,2! +]. * triazine— 25 k * on

CIX 6 (7 l * Methyl-3 * phenyl-1,6,7,8-tetrahydroimi— mp: 200 * 201 ° C

dazo [2.3 * c] [3.2, U] -triazine-h * on

CXXI 8 * myl * 6 (71-met & yl-3 * phenyl-i, 6,7,8-tetra- m.p .: 99 ° C

hydroimidazo [2,3-c] [1,2,3] triazine-1-one

30 CIV 3- (1 * cyclocycloBfixyl - 6,7,8 * tetrahydro - mp: 170 ° C

imidazo [2, J * c] 11 µS-1-Riazine-A-one

CV 3 * (1 * Ethoxycycloheryl Ι-θ-met hyl * i, 6,7,8-- Mp: 1Q2 ° C

tetrahydroimid'dazo [2.3 * c] [1,2] triazine-U * on

35 cvx 6 (7i * Metbyl * 3 * -phenyl * 8-propyl-1,6,7,8-tetra- Mp: 1Q7 ° C

hydroimidazof 2,1-c] [.1,2, U] * triazine * i-one 8400013

Example Connection name Physical constant - * Λζ -

CVII 6 (7J-Methyl-3-phenyl-8-propyl-4,1,7-8-tetra-mp: 168 ° C

hydroimidazo [2,1-c] [1,2,4] -triazine-4-one, (decomposition) 5 hydrogen nitrate

GVIII 3- (1-Ethylcyclohexyl] -8-propargyl -4,6, 7,8- m.p .: 71-72 ° C

tetrahydroimidazo [2,1-c] L1,2,4] -triazine-4-one

CIX 34 l-Methylcyclopentyl) -4,6,7,8-tetrahydro- Mp .: 239-24Q ° C

Imldazo [2,1-c] [1,2,4] triazine-4-one

CX 3- (1-Methylcyclopentyl) -8-methyl-4,6,7,8- Mp: 104-105 ° C

tetrahydroimidazole; 2,1-c] [1,2,4] triazine-4-one

CXI 343-Methylcyclopentyl ί-8-propargy1-4,6,7,8- Sm. p.:1G5 ° C

Tetrahydroimidazo [2,1-c] [1,2,4] -triazine-4-one

CXIX 34i -Methylcyclopentyl) -8-propargyl-4,6,7,8-Sm. p .: 148 ° C

tetrahydroimidazo [2,1-c] [1,2,4] -triazine-4- (decomposition) on

20. CXITI 8-Allyi-342-chlorophenyl 1-4,6,7,8-tetrahy- m.p .: 211 ° C

droimidazof2,1-c] [1,2,4] triazin-4-one

The following examples further illustrate the possible uses of the compounds according to the invention, which were used in the form of port-indicated preparations.

Example CX1Y.

In a greenhouse, the compounds of the invention listed in the Table were used in an amount of 3 kg of active compound-3Q d ± ng / ha, dissolved in YQu liters of water / ha, on Sinapis (Si), Solanium (Sol and Setaria (Se) sprayed as plants to be tested after emergence The treatment result was assessed according to the valuation schedule Q to 4 3 weeks after the treatment, where CL - no effect means 35 = destruction of the plants As shown in the table , as a rule, was a destruction v, ..

8400013 - IT -

Compounds of the invention JTa emergence

Se Si So of the test plants reached.

5 8-Methyl-3-phenyl-4,6,7> 8-t etrahydroimidazo [2,1-c] - 4 4 4 [1,2,4] -triazine-4-one 3- (3-Methylphenyl 1 -4,6,7,3-tetrahydroimidazo-4 4 4 (2,1-c] [1,2,4] -triazin-4-one 8-Methylsulfonyl-phenyl-4,6,7,8-tetrahydroimidazo 4 4 4 [2,1-c] [1,2,4] -triazine-4-one 3-tert-Butyl-8-methyl-4,6,7,3-tetrahydroimidazo— 4 4 4 [2,1 -c] [1,2,4] -triazine-4-one 3-tert-Butyl-8-methylsulfonyl-4,6,7 s8-tetrahydro-4 4 4 imidazo [2,1c] [1,2,4 ] -triazine-4-one 3-tert-Butyl-8-propargyl-4,6,7,8-tetrahydroimidazö- 4 4 4 [2,1-c] [1,2,4] -triazine-4-one 8-Chloromethylsulfonyl-3-phenyl-4,6,7,8-tetrahydro-444 20 imidazo [2,1-c] [1,2,4] -triazin-4-one 8-Allyl-3-phenyl-4 6,7,8-tetrahydroimidazo [2,1-c] - 444 {1,2,4] -triazi, ne-r4-one 3- (4-Fluorophenyl 1-4,6,7,8-t etrahydroimidazo [2,1-c] - 444 25 D, 2,4] triazin-4-one 8 - (2 ^ Butenyl I-3 - - - phenyl-4,6,7,8-tetrahydroimidazo- 4 4 4 12,1 -c] 1,2,4,4-triazin-4-one 8-Methylmethyl-3-phenyl-4,6,7,8-tetrahydroimidazo-4 4 4

{2, J-c] 1,2,4] triazine-4-ron 3Q

3 ^ enyl-6,7s8,9 ^ etrahydro-4ff-pyrimidino [2,1c] * 1 + 4 4 i J, 2,4] -triazine-r4-one 2 ^ (2-Butenyl-1-3) phenyl-6,7,8,2- * tetrahydro-4E-pyri-4 4 4 midinof2,1-c] [1,2,4] -triazine-4-one 35 8-Allyl - 3-tert-butyl 4,6,7,8-t-etrahydroimidazo-4 4 4 X 2, J-o [-1,2,4] -triazine-4-one 8400013

Compounds According to the invention iTa the emergence

Se Si So - 18 - 8- (2-MethyI-allyl J-3-phenyl-Λ, 6,, 6,, 8-t etrahydroimidazokkk [2,1-c] [1,2 i + j-triazine -Λ-οη ^ 3-Phenyl-9- (2-propenyl \ -6,7> 8,9-t etrahydro-4H-pyrimikkk dino [2,1c] [1,2,2] -triazine-4 -one 3- (^ -Fluorophenyl 1-8-methyl-4,6,7,8-t-etrahydrimidazohine U ^ [2, Tc] [1,2] triazin-4-one 10 3- (^ - Fluorophenyl 1-8-propargyl-, 6 ", J, 8-t etrahydroimil] (Ij.

dazo [2,3-c] [3 ^ ^ 1-triazine - ^ - on 3— (3-Methylphenyl 1- ^ 8-propargyl- ^ 6,6,7,8-t etrahydro-kkk imidazo [2 .1 -c] [1,2, h] -triazine-Λ-οη 8-Methyl-3 ~ (3Haethylphenyl 1-4], &, 7, 7-etrahydroimikkk dazo [2J] [1, 2, Uriazin-4-one 3-tert-Butyl-2-methyl-7,8,9,9-etraphydro-4-pyrimi- [ihh diho {2} 3-c] [1,2]] -friazi 4'-4-one 3-Phenyl-r-9- (2'-propyllyl-6 ', T, 8,9-tetraB, ydro-it-pyri-3-midiof2,3-c} [1, 2, k-t riazine-1-one

3-tert -Butyl-9- (2-propynyl 1-6 ", 7,8,2-t et rahydro-1 + H-b U U

pyrimidinof 2,3-c] 1,3,2,11-triazine-4-one

3-cyclohexyl ^ 1 ^, 7,8 - tetraaydroimidazo] 2)] - c] ^ U ^ U

25 f 3, 2 µl-triaz: -in-k -one 3-Isopropyl-8-methyl-1, 6, 7, 8-tetraphydroimid'dazo-k [2,3-c] 13, 2? You] -t riaz £ ae - ^ - on

9- Methyl-3-phenyl- ^ iT, 7,8,9-t etrahydro- ^ E-pyrimidino- ^ k U

[2,3-c] f 3, 3-triazin-1-one S-cyclohexyl-S-methyl-6, 7,8,2-tetraflyroimidazokkk £ 2, J-3-c] f 3.2 , U] .- triazine-Λ-οη 3-Cyclohaxyl-8-propargyl - ^, 6 \ 7,8-tetrahydroimidazokhkf 2,3 · τθ] 13, 2, ^] - tri: azine-W> n 35 8400013

Compounds according to the invention After emergence

Se Si So - 19 - 3-Cyclohexyl-8-diethyl-4, 6,7,8-t etrahydroimidazotin-4 4 [2,1c] [1,2,4] -triazine-4-one ^ 3- Isopropyl-8-propargyl-4, 6,7,3-tetrahydroimidazo-4 4 4 [2,1-c] [1,2, h] -triazine-4-one 8-Allyl-3-isohutyl-4,6 ^ 7.8 ^ etrahydroimidazo [2,1-c] - If.i4.14.

[1,2,4] -triazine-4-ol 10 9-Allyl-3-tert-Butyl-ti, 7,8, J-tetrahydroimidazo-1+ 4-4 [2,1-c] [1 , 2,4] -triazin-4-one 3-tert-Butyl-6 '(7l »8-dimethylphenyl, 6', 7s8-tetrahydroimi-> 4 4 4 dazo [2,1c] [1,2, Triazone-on-8-cyclohexyl-3-phenyl-lv, 7,8-t-rahydroimidazo-kkk [2, Jc] [1,2,4] -triazine-4-one 3 ^ 2,5 ^ ichloro-3- * thienylI-8 (1 L - methyl-4,6,7,8-tetra-4 4 4 hydroimidazo [2,3] - c] 11,2,4] - > triazlne-4-one (Isomers mixture) 3- (2,5-Dichloro-3 - ^: β-yl] - 8- ^ propargyl-4, ^, 7,8-tetra-4-4-hydroimidazo [2, J- * c] [1 »2,4] ~ triazone - 4-among others 3-Isobutyl-8-propargyl-4, 6, 7, 8-trahydroimidazo-4 4 4 [2,1 -c] [1,2,4] -triazinhe-4-one 25 3-tert-Butyl-8-methyl--1-, 6 ', 7,8 ** 4: etrailydimimidazo [2.4 4 b- c] [1,2,4] triazin-4-one, hydrogen nitrate B-tert-butyl - ^ - chloromethylflyisulfonyl-, 6,7,8-tetrahy— 4 1+ 4 droiaiidazo [2, - c] [1,2,14] -triazine - ^ - on 2q cl (71,3-triiiietayl ^ 3-phenyl-^, S ', 7 s 8-t et rahydroimidazo— 4 4 4 [2, Itc} [J , 2,4] -triazine-4-one 8 (7I-Methyl-3-KphenylT3 ^ propargyl-4, 6,7,8 - * t et rahydro- 444 imidazof2, Jc] [1,2,4] -triazin-4-one S-rtert ^ Sutyl ^ eHnetfiozymethyl-lt-ji, 7,8-tetrahydroimi- 4 4 4 ^ dazo [ 2.1-h:] [J, 2.4] -triazine-4-one 8 0 0 0 1 3

Compounds of the invention Ia emerging

Sa Si So - 20 - 8-Methyl-3- (2-thienyl) -, 6,7,8-tetrahydroimidazo-bbb [2,1-c] [1,2, k] -triazine-4-one ^ 3-laobutyl-8-methyl-1 (-, 6,7,8-tetrahydroimidazo [2,1-kbbc] [1,2, ^] - triazin-4-one 8-Allyl-3-diaopropyl-1 | - 6,7,8-tetrahydroimidazo [2,1-bbbc] {1,2,1 +] triazine-4-one

10 3- (2-Hydroxy-1,1-dimethylethyl} -8-methyl-1), 6, 7, 8-Hl + U

tetrahydroimidazo [2] -1-c] [1,2,1 + j-triazin-1-one 3- (2- ^ Hydroxy-1,1-dimethyl-ethyl] -8-propargyl-6,7 8- b U b tetrahydrolmldazo [2,1-c] [1,2] +] triazin-4-one ^ 3 ^ methyl-8-propargyl-4,6 ', 7,8-tetrahydroimidazo [2, 1-bbbc] [1,2, ^] - triazin-1-one 3-Clopentyl - ^, 6,7,8 - <»tetrahydroimidazo [2,1'-c] - 1+ Λ b (j, 2, ^] - triazxne-4-one 3-Cyclopentyl-8-methyl-k, 6 ', 7,8-tetrahydroimidazo-U ^ 1+ ^ [2, Jc] [1,2,! +] - triazineJ + -> on 3-Cyclopentyl-8-propargyl-1 +, 6 ', 738 ^ tetrahydroimidazob. [2,1-c] [J ^ j ^ triazine-i-ron 8-Allyl ^ 3-cyclopentyl ^, 6', 7,8-rtetrahydroimidazo [2,1-bbb 25 c] _ [1,2,2 +] - triazine-J + -one 3-tert-Butyl -? - 8-methyl-6,6,8,8 -r-tetrahydroimidazo] 2,1- b U bo] {1,2, b] -triazine - ^^ on

3Q

35 8400013 - 21 - $ 0-3--3- -3- -3- -3 -3- -3 -3 -3 -3- o d5> Μ

YOU

<υ α> Ό C Ö · Η -3 -3 -3 -3 -3 -3 -3 -3

Cd <υ <Ώ

> I

Ö0 3d Ο ft • Η Ο «η -μ cd υ ft Λ OCdHJ-3-3- -3 -3 -3 -3 -3 -3 -3 -3

Eh fiCQ

S3 I.

I ^ I

ι <υ -3 ’-3 ö * -3

I · Η <Μ - ι. I

<»TJ * CM —1 1, 3 3 - ^^ - $ h - - evi w"> 3 Ύ YU— «cm—" "77 7, -L, 7 I '- CM« Ο - o

ij - - 1 - 1

ι - cm »ο ο ·" "7.77" U ^ - t 2L l 2i

= 3 S ^ a ^ I cv, I

- Y-axis 8 -3 -s * 0 I

7! ft 3 a <tf k Ο -H N 5

Ο * ο · η Ό -p 2 § j * 3 S

1 CM k 0 * H jJ ®! "7 .3 O

7 s 3,, ¾ 3 § 3 8 s 8 eu * 8 II g I 3% * 3 t «- · CQ Hi Λ H -W rn p 2 ^ rj Ti k CÖ * 0 <U Ο Λ 2j 73 § 3 5 £ & -μ £ ΰ0 Yy

._! c ij + j SZ I Ό ίπ jJ

Ό · η -μ <D djCO -ji 3 "S

* g £ co i +> * - g *? *? , 3frt λ co ¢) * »k j -J,

«* 1 1 -3" VO ®. VO

1 έ I i t <ύ -: ^ 5 i 3 -Ö CO Λ >> -3 -7 VO Η »η ff ~ | ϊ 1 s3 • 5 ι -: J I I I H I I a a i 2 ΰ? S Sol L s ft § § <* - s «f? 2 1 l JS 4JI * Π J> 2 1 3% £ «cm ΐ) 5 UO3 0 ^ f £ £ 0 i -rSl £ 38 £ 3> 3> 7> 7 2 c £ ö Λ c 3 fc S3 To § 3 ΛΛ'δίο ^ Ο-'Ο IcdCMOftcdonoftcd

1 $% 2 1 i I J. A i St T i S t Ύ J I -C

.S iis S i 5 IJIS ΐ 7 · 2 1 3 3 J, Ό I ΙΛ 1C <UC> »CO 1 — '7Sr3 ^ 775S-ac + J + J -3 -HS -Η Λ -H s - 3>. -H o J->, -H y -3 ^, _j u U * «tj IM + Jï ^ ι» iH I * 7 5 Jl -ι δ m cu e cnas coas <uc - 'oj ^ ° 3 ojcm hd 3 w + J + JO -H -HS -H - "*? '7 7" - IL 7 r- «A ^ i ^ SASdSS-siiA-cAiA-- ♦ 8400013 - 22 - 0 0 -4 · -4 · -4 · -4 · -4 · -4- -4 - = f -4-4-

CS CQ

Ή

• H

G

O

>

O

d G G -H -4 -4 .4- -4- -4 * .4- -4 · -4 · -4-4

Cd <U CQ

s> § o ÖD d G ft

• rl O

rn-

ta p cd o ft Λ O

O Si HJ 4 -4 · -4 "-4- -4- -4 · -4" -4 "-4-4

& H S3 CQ

ri, i Y i 1 ". i; r- .-. - 1 1 i, g

«O O 3— <—l f. G

OJ II «-4 · 3- l · * V 'Ö u_i r- r- CM» «O Θ 3-1> for« Ki — i CM CM OS CS «· d« CM cm O «· - · CD CD CM CD

Cd 1_1 _v CS * 3— O 'Ö Ό --1 G

d o o— cd —I, 63 · Ή 't ± O P

• h es es d i — i ‘cd S S 3 <d g cd cd ή y Η · ή · ·> +« 3 +3 • η d xt S I · Η O O d I; O · Η · Ρ · Η <- S G G · Η. co G g g o »· ή H d S - * d · Η · Η G CM O> 3r> 3r 'rl C—>» O O d ^ G 6 -S p

dGSs ^ OdcdaJGMO

cddddeS ^ GGP "· G> 3> 5 cd cd d P P b · -4 p λ d g d cd. o o fS i · o cd cd p -'h G p p a * - *

p G G 4> S pi J s ^ H

| +3 +3 +3 · Η - O CO CO +3> 3 · CO o O I O P «-« O ft «p p co? H i c— c— -po

f— ((«d CO '»' «V G

«CO <33 t— |>» "· MO VO 00 ft

\ Q «« «this—« «« O

«£ - f— MO cd" -4 -4 t— H

-4 · "« «GO l · t ** O

| MO MO -4 · -p «HHMOi> rC3

ÜO H «« l · 0-4> *> v * O O

Ö Λ -4 H -P 1 · öfl · dfl "-4" H r • rl 60 II> 3 H G. GI £ »-4 · d GH öO oo S cd d Λ t G cd H> 5 G" d ft ft H £ .η ft sd cd ί- -po ^ pgg> o> «j +3 ft« (ü J4S3SÏS3-P s-r +

-p Ss O <U O MO S ft O 'ft O S3 f'N

rl ft di s 5h - V ννννο-τ-ιιί

2 I O I ft -4- CO CO -4 "CO -4" ft l'-P

CO H CO I · i V kl'l'l'O Sjk

<U | O 1 CO r- * d '-r <U r ~ 4 (UHaO-P

d>, --S t H HOHÖHÖUOOI> HOO ö H ö rr β S> »I>) ·> +> V • rl-> 3 · Ϋ H '-' cn> 3 O HO> 3-0H0-P 43j -43N + 3 ^ ü- = T ^ - = 3- ö i> 3 i «i>» i · a Cl · ö „cd c aj; h v o «·

<U 0-4 · d3 -4 · 0-4 "X -4" O O O O · γ + O · Η ·> 3- O · Η- CM

ÖO d3 I -PI d3 (OI ft ftaft & rftSrd3G'd "· H OOOOOOdiOO o · ν + O +? O -p -P · Γ + P r- O HG g G HG OGH H ^ HI Ht O NCM" -> OH 1'POHH'HO OCÖO '-> O <-' S Ö «'-'> 3 es r— es Pj es o es> 3 · G> 3 · ·> +, f» * · -4- t> y -4- I Ή CM 9 a O Cd rr Cd OCd> 3'G OO OGi OH * ri! * Rl ^ 3'p Ü * HH \ r HP HCM HCM rr pk ÖO>, GCOG XG HG> Ï -4 · > 3-1 ·> »" b '"^« Γ

G dip lp OP> * P dl Λ · - di r- d3 r-! CO -1F CM

• H PI Hl dl · dl · PO P-4- P '-' P r— »I '-4 · H - <

d O r- ~ i> 3 1 — I P I — I P 1—-1 O G O O "1 O I—> H« ·> 3 · O

G s -4d-4S 4 S-4- g "-Γ + STCM Sjo So> v CM P N

• H 1 «p« 1 «1« 1 · cJ Ι · «· Ι · Ι 'I' \ t H« O cd d r-CM O CM 3— CM r-CM r-cd rr- rr- tr r -, H '-' yd -—- «S« '- «> - ·» —- · Γ +' - 1> rr "-" = 4. 1 <4γ +

o I 3— | 3- 1 3— I 3- IG I'— “ICCMV” —1 t S

> CO / 1 CO> CO · 1 00 1—1 COp COO CO · -> OO · —1 CO O CO <r + 8400013 - 23 -

Example CXV.

In a greenhouse, the plants listed in the table were treated with the compounds to be tested in an amount of Q, U kg of active compound / ha to be used. For this purpose, the compounds were uniformly applied to the soil as 5 solutions or suspensions in water, with 500 liters of water / ha.

The treatment result was evaluated according to the rating scheme 1 to 10 3 weeks after the treatment, where Q = total destruction and 10 = 10 no effect.

The results show that, in contrast to the comparator, the compound of the invention exhibited better tolerability and activity.

15 8400013 O '- 2U - sraaojig aoo cu o soTqootx ^ still ooooo 3og ° ° ° σ 2 snjnosdoiv ο ο ο <- o' BJcnq.'Bg ο ο ο ο o sxtreqsss ο ο o ° 2 esonxodx o ο o mo θχ ooooo 'exjBox ^ q.'BM ° ° ° σ o • bxjbXXS' + S ο σ ο σ o sxd'Bnxg ο σ o ° 2 w — Ή ^ .sCxa 2 2 2 o ^ 2 * STTW 2 2 2 2

P

Xadd ^ pjev 22 2 "u 2 2 43 bCos 2 2 2 J 2 2 0 l · 0 cd S-i i i S3 ^ p

Ο Ο Ο P S3 O

fn Sj I DO O

s <o ρ p i - - c> 5! >> I I Ρ Λ 0)

43 43 0) CO> O S

aj S3 cd s3 «* 0) or I

S-ι Ο S-ι · Η t— S3 -pm

-μ | · ρ d *> -rl b £ I

bfl 0 p 0 cd MO N Η O

Ö ρ I p -rt "cd O £ -1 • Η 10) I U Ρ -Η M Xj <d CO S3 ON p I Sn,> s S3" -Η "I HP CD 43 fl

• H C— N CO i ** i 1 = ¾ i S3 * r + O

!> «Cd« P 43 —- Ο Ό I · p MO -H f- «p p be V li>

• H »? H« CM 0 "· r-Γ ΙΓ \ I

S Ρ p MO "· S CM O -v0 II I T- .rl«> · P S3

0--H r — i i — l '—1 S' - "ί -H

S> 4 p> ji — I I'— I H n 43 * 43 o co. — I H> v cd CO P CM P I "0 0Ρ · Η · 0 00 01- ^ 1 Ό 3? -F

a; S'- fi <* t— »- Ρ -P

SO I I — I T CM · Η | · \

, -1 CO ™ ON -> MO CM S-UP

O I Ü I 0 I - 01 P

> HIHs3HO ÖC 0 CM _ 1 = ¾> - 1 = ¾ -P!> »= 1 S3 +? ~ T3 60 ρ Λ -Ρ Ό -P cd · Η · (• 'T Η C 3 cm 3 · η 3 S ii v) I 0

• Η Ρ3 - fq g Ρ3 · Η ---: 10 S

Ό I Ο I -Η i S Ή Ο Ή · S3 3 Ρ Ν -Ρ? -T -Ρ · Η · Η S3 43 Cd • Η Sh 0 U> ϊ Ρ Ο 0 · Η · Ρ 43 S 0 Ό 0 S3 * 0 4r ÜCS'r-l 0 Μ ρ · Η ρ I Ρ Ο Si <! > J 'Ρ 0 I S I ES I-> v 0 t 43 S3> m · η m p- ms> 4 ρ p O · 8400013 - 25 -

Example CXVI.

In a greenhouse, the plants mentioned were treated with the compounds listed in the table after application in an amount of 0.1 kg of active compound / ha to be used. To this end, the compounds were sprayed evenly over the plants as an aqueous solution or an aqueous suspension with 500 liters of water / ha.

The treatment result was evaluated according to the rating scheme 1 to 10 3 weeks after treatment, with 0. = total destruction and 10 = 30- * no effect.

Also, 3 weeks after treatment, the compounds according to the invention showed a greater selectivity with excellent action against the weeds. The comparator did not show this selectivity.

♦ 8400013 V V- - 26 - • eoj oo-oo σ o snjnaosdoxv o · ooooo ssjrvBqxrao oooooo 'ΒχοτΛ oooooo ^ TXSOT.iq.'Bjtt ooq σ σ o' Bt.rsxxsqs oooooo q.sj: SA O o r- ° r - *> r “r · - r“ * Λ Λ 1, J * O Pt 00 <L)

»I“ G

OJ t <“OJ Ο · Η • Λ I" 1 1 Λ Ο £ * ·· · fcsj r- Ο (Μ τ ~ CÖ ι__ I -> <-> Ο · Η. Γ · Ο ι "" r VO 5+ CJ "G Ο -Ρ I CM · Η t -Ρ I · r— —ld ft r- 'Ï-i - = ί *« Ο · Η ή * Ή Λ

OJ 63 S OJ U CM

ι —- J CÖ Ή> —d ft Λ ο ft 5+ ο Ο ΟΝ -Η> 1 01 03 1

es S ft CÖ / HO

> 0 · Η 1 πΟ Ο · Η • Η Ο Κ · Η Oft s 5+ -a- a 5+ -ρ • Η ft I -Η Ή Η ο> »ο ο α>, Μ ft 5+ 5+ Ο Λ

ft cd ft ft + J

ft +3 ft ft Ο g cd <u cd cd co (u -P 5+ u -H oo +3 l -P +3 6 £ f

60 ¢) CO 0) (0 HO

G +3 «+ a -P Ο pH

• ή · ι c ~ ι i «ft ft co" CS oo! >> g «vo nn 03 ft • r + t— * OO t— G -rl 0 ~ {- Λ Λ (33 ft +3 VO IC ~ VO 60 I • • Η ** Η λ η H ir \ G - = r> 5 so -a · 0 1 60 ι t> - = r OH 5+ GH Ö H - i

ft> s cdo> sa> 5H

ft ft I ft 1 ft H> »

03 +3 OPt + 3Pf-P (U-P

ö <u s + ι <u ι ο ft o <us ft <us <u- e ftft 60 I t GIGI η H 60 CO -rl OS H CO S + 3 O 1 GI 03 (6) 1 G 03 if> HO HcdHcdHO 60 Φ

!> J I> »-H> 3 -H> 3 t G -P 'G

60 + 3J- + 35 ++ 35 +! * I-3 Ή y H

a ο ι g -pg + j φ t ft so φ • H ftoftlftlfto - <- = 1 ft ft IGI r — i 1 1—1 0Π -rl og G + 3.ΓΙ + 3ΡΓ + 3-4-Η- G HG Cd • rl 5 + 63 5 + - 5 + 0 Otf Φ -H ft ft Φ cd Φ. CM 1) CM> ïCd 60 S G <0 5+ + j-h + 3 "+ Jo0.h 5+« 50 ft

Φ 15+ i o- I r · ι 5+ (Dll G

> oo +3 oo —.oo · —.00 + 3> -3-lon o 8400013

Claims (5)

1. Triazinones of the general formula 1, wherein: R 1 is hydrogen, an C 1 -C 6 alkyl radical optionally substituted by halogen and / or cyano and / or hydroxyl and / or C 1 -C 20 alkoxy, an optionally en-5 or C 1 -C 2 cycloalkyl radical substituted by alkyl and / or halogen and / or phenyl, a C 1 -C 20 alkoxycarbonylmethyl, an optionally single or multiple C 1 -C 20 alkyl and / or halogen and / or C 1 -C 2 -alkoxy and / or a nitro group and / or a trifluoromethyl group substituted substituted aromatic or aramatic-aliphatic hydrocarbon radical or a heterocyclic hydrocarbon-ato radical, 3 * 2 hydrogen, optionally singly or multiply by halogen, C 6 - C 1 -alkoxy, cyano, C 1 -C 6 -alkylthio and / or hydroxyl-substituted C 1 -chalky 1-, C 1 -C 8 alkenyl, C 1 -C 6 alkynyl, C 1 -C 5 cycloalkyl or cycloalkenyl residue, a C 1 -C 8 alkyl radical, which is optionally single or multiple interrupted by oxygen, sulfur or nitrogen, a C 1 -C 6 alkoxycarbonyl-C 1 -C 2 alkyl, an optionally enhel or multiple halogen C 1 -C 8 alkyl-sulfonyl group or an optionally single or multiple, mutually identical or different from C 1 -C 8 alkyl, halogen, C 1 -C 2 -alkoxy, a nitro group and / or a trifluoromethyl group substituted aromatic or aromatic -ali-20 represents a fatal hydrocarbon radical, R 1, R 2 and are mutually the same or different and each time hydrogen, an optionally singly or multiply halogen-substituted C 1 -C 6 alkyl group, an optionally singly or multiply, mutually the same or different aryl radical substituted by C 1 -C 8 -alkyl, halogen, C 1 -C 2 -alkoxy, a nitro group and / or a trifluoromethyl group and is n-Q or 1, and the salts thereof with inorganic and organic acids. Triazinones according to claim 1, wherein R 1 phenyl, 2-methylphenyl, 3-methylphenyl, 1-methylphenyl, 2-chlorophen-30-yl, 3-chlorophenyl, L-chlorophenyl, 2,1-dichlorophenyl, U-fluorophenyl, U -trifluoromethylphenyl, 2-thienyi, 2,5- <-chloro-3-thienyl, isopropyl, sec-butyl, tert-butyl, chloro-tert-butyl, 2-hydroxy-t, 1-dimethylethyl, methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, cyclopropyl, cyclopentyl or cyclohexyl; R2 is methyl, ethyl, propyl, allyl or propargyl; 8400013 5 v »-> 28 -λ R, R ^ and R, - each represent hydrogen or methyl and n = 0 or 1. 3. 3-tert-Butyl-8-propargyl-U, 6 ', 7,8-tetrahydroimidazo [2,1-c] [1,2,4] triazin-1-one. 5 h. 3-tert-Butyl-2-methyl-6,7,8,9-tetrahydro-1H-pyrimidino [2,1-c] - [] i] -j-triazine - ^ - on »5. 3-Cyclohe; xyl- 8-methyl-4,6,7,8-tetrahydroimidazole-2,1-c] [1,2, U] triazine-h-one. 6. 3-tert-Butyl-6 (7) 08-dimethyl-h, 6,7,8-tetrahydroimidazo [2,1-c] -10 [3,2,4] -fibriazine-U-on .. 7 1,3-tert-Butyl-ethyl-44,6,6 ', 7,8-tetrahydroimidazo [2,1-c] [1,2,6] triazine-h-one. 8. Process for the preparation of tiazinones, characterized in that the compounds according to any one of claims 1-7 are prepared according to a method known for analogous compounds. 9. Process for the preparation of triazones, characterized in that the compounds according to any one of claims 1-7 are prepared by: reacting all compounds of the general formula II or the metal compounds thereof with compounds of converting the general formula 3, optionally in the presence of acidic agents and in the presence of a catalyst or compounds of the general formula k, optionally in the presence of bases, with either compounds of the general formula 5 or - insofar as Rj represents a C 1 -C 8 -alkoxycarbonylmethyl radical-25 to react with compounds of the general formula 6 or compounds of the general formula 7 with compounds of the general formula 8 or di compounds of the general formula 9 to converting with compounds of the general formula 10 'or 3Q e [compounds of the general formula 5 in the presence of ha.s: and converting with compounds of the general formula 11 and the compound of formula 12, wherein R 1, R 9, R 7, R 7, R 7, and n have the above meanings, X a halogen atom, a sulfate or a tosyl group, an oxygen or sulfur atom, R 8 hydrogen, a methyl or ethyl radical and 8400013 - 29 - Κγ a C 1 -C 2 -alkyl radical. I.Q. A process for the preparation of an agent with a selective action as a herbicide, characterized in that one or more compounds according to any one of claims 1 to 7 are introduced into a suitable form of herbicide, 11. Selective-action molded herbicides obtained by the process of claim 10. 10 I # 8400013 2 y -ψ * N 1 wo / II oj | l 3 - R ~ ^ N- ^ N - H Rkc · ^ - S R5 ^ 4— S3 * 2 '* 5. k Η2Κ 5 ή \ * i- ^ ° 6 IW R? QQC - C = C - COOH ^ ff - Ra 0 ^ === 5 - OH. V ^ ca, ^ I 11 S3 R% 7 8 9 f *. H ^^ N'NH2 \ ~ γη, JU —1 f IH ^ {C ^ n a3 O - === ^ OR 51 R * 11 10 Η N HN-R 12 x X 3 I VnchX-r i R- - Mcnr— ηλ I j h.nnh ^^ sch 3. n 3 r 2 J Schering Aktiengesellschaft 8400013