NO141300B - HERBICIDE CONTAINING SUBSTITUTED 6-AMINO-S-TRIAZINDION DERIVATIONS - Google Patents

Description

The present invention relates to herbicidal agents containing

a new group of 6-amino-s-triazinedione derivs.

Neumayer et al., "Pesticides", Chemical Week, 12 and

April 26, 1969, lists several commercial and experimental s-triazine herbicides. Among these, two well-known products are atrazine and simazine:

US Patents 3,505,323 and 3,505,057 disclose a class of tetra-hydro-s-triazinones of formula A below and their use as herbicides. DAS 1,962,797 discloses a class of s-triazinones of the formula B below and their use as herbicides.

Q = S or O n = 1 or 2

X = halogen X = S or O

Y = H, halogen, alkyl etc. R 1 , R 2 and R = H or alkyl

R and R 1 = alkyl

Chem. Pray. 104, 1606 (1971) states the preparation of s-triazine ethiones by cyclocondensation of ethoxycarbonyl isothiocyanate with amidines, isoureas, isothioureas and guanidines:

where X can, among other things, mean (C^H^^N-, (C2H^CH2)2N- or (<C>6<H>5)2<N>-.

The present invention relates to herbicidal agents which as active ingredient contain a compound with the general formula: where R^ means alkyl with 2-8 carbon atoms, alkenyl with 3-6 carbon atoms, cycloalkyl with 4-8 carbon atoms, cyclohexenyl, norbornyl, norbornylmethyl, trimethylcyclohexyl or tetramethyl-cyclohexyl, or the above-mentioned cycloalkyl groups substituted by one alkyl group with 2-4 carbon atoms, 1-2 methyl groups or 1-2 chlorine or bromine atoms, or R^ is

where Q is hydrogen, fluorine, chlorine, bromine, nitro or trifluoromethyl, Y is hydrogen, chlorine or raethyl,

R„ is hydrogen, methyl, ethyl or a cation comprising Na, Li, K, (Ca/2), ammonium or dimethylammonium,

is hydrogen or methyl,

R^ is alkyl of 1-4 carbon atoms, and

X is oxygen or sulphur,

with the proviso that when X is sulfur, neither R 2 nor R 1 is hydrogen.

Of the compounds covered by formula I, those are preferred where R^ is alkyl with 3-6 carbon atoms, cycloalkyl with 5-8 carbon atoms or cycloalkyl with 5-8 carbon atoms, substituted with a methyl group, and where R^, R^ and R^ is methyl and X is oxygen or sulfur.

More preferred are the compounds of formula I where R 1 is cyclopentyl, methylcyclopentyl, cyclohexyl or methylcyclohexyl, and where R 2 , R 1 and R 2 are methyl and X is oxygen.

Most preferred is the following compound: 1-methyl-3-cyclohexyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione.

The compounds of formula I and their preparation are described in Norwegian patent 140 268.

Of active compounds of formula I which can be used in the present agent, mention may be made: 1-methyl-3-cyclhexyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 97 - 100.5 C

1-methyl-3-cyclopentyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 126 - 129 C

1-methyl-3-cyclohexyl-6-dimethylamino-s-triazine-4-thio-2,4(1H, 3H)-dione, m.p. 210 - 212 C

1-methyl-3-(p-fluorophenyl)-6-dimethylamino-s-triazine-4-thio-2,4-(1H,3H)-dione, m.p. 224 - 226 C

1-methyl-3-(m-fluorophenyl)-6-dimethylamino-s-triazine-4-thio-2,4(1H,3H)-dione, m.p. 204 - 2o6°C

1-methyl-3-cyclohexyl-6-dimethylamino-s-triazine-4-thio-2,4(1H,3H)-dione, m.p. 210 - 212 C 1-methyl-3-ethyl-6-dimethylamino-s-triazine-4-thio-2,4-fih, 3m-dione. m.p. 139 - 140°C 1-methyl-3-(n-butyl)-6-dimethylamino-s-triazine-4-thio-2,4(IR,3H)-dione, m.p. 124 - 126°C

1-methyl-3-phenyl-6-dimethylamino-s-triazine-4-thio-2,4(1H,3H)-dione, m.p. 209 ~ 211 C 1-methyl-3-(o-fluorophenyl)-6-dimethylamino-s-triazine-4-thio-2,4-(1H,3H)-dione, m.p. 220 - 221°C

1-methyl-3-(m-fluorophenyl)-6-dimethylamino-s-triazine-4-thio-2,4(1H,3H)-dione, m.p. 204 - 206 C

1-methyl-3-(p-fluorophenyl\-6-dimethylamino-s-triazine-4-chloro-2,4(1H,3H)-dione, mp 224 - 226°C

dimethylammonium-3-isopropyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 213 - 215 C

3-isopropyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 213 - 214°C

sodium 3-isogropyl-6-dimethylamino-s-triazine-2,4(,1H,3H)-dione, m.p. above 300 C

3-cyclohexyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 279°C (decomposition)

3-(t-butyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 206 - 209°C

3-(sec-butyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 161 - 164°C

3-(p-chlorophenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 265 - 267 C

3-(3-pentyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 148 - 151°C

3-(3,4-dimethylcyclohexyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 234 - 237°C

3-(4-t-butylcyclohexyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 283 " 285°C

3-isopropyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 213 ~ 214°C

3-isopropyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione-dimethylamine salt,. m.p. 213 - 215 C

3-isopropyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione lithium salt, m.p. >300 C

3-isopropyl-6-methylamino-s-triazine-2,4(1H,3H)-dione-=j>-calcium salt, m.p. > 300 C

3-isopropyl-6-methylamino-s-triazine-2,4(1H,3H)-dione sodium salt, m.p. > 300 C

1-methyl-3-isopropyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 104 - 106 C

1-methyl-3-(t-butyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. l6l - 163°C

1-methyl-1-3-ethyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 104 - 106 C

1-methyl-3-propyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 106 - 109 C 1-methyl-3-isopropyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 104 - 106°C

1-methyl-3-isobutyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 87 - 89°C

1-methyl-3-butyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 63 - 65°C

1-methyl-3-(sec-butyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

n^<5> 1.5198

1-methyl-3-isobutyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. l6l - 163°C

1-methyl-3-neopentyl-6-dimethylamino-s-triazine-2,4 (1H,3H)-dione, m.p. I4l - 144 C

1-methyl-1-3-hexyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

n^<5> 1.5130

1-methyl-3-allyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 74 - 75°C

1-methyl-3-(3,4-dichlorophenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 211 - 212°C

1-methyl-3-(2,5-dichlorophenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 191 - 194°C

1-methyl-3-(p-chlorophenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 238 - 239°C

1-methyl-3-(m-chlorophenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 141 - 143°C

1-methyl-3-chlorophenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 205 - 207°C

1-methyl-3-(m-fluorophenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 157 - 159°C 1-methyl-3-(o-fluorophenyl)-6-dimethylamino-s-triazine-2,4(1H, 3H)-dione, m.p. 179 - 182°C

1-methyl-3-((3-chloro-6-methylphenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 155 - 157°C 1-methyl-3-((3-chloro-4-methylphenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 189.5 - 190.5°C

1-methyl-3-[m-(trifluoromethyl)-phenyl]-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 144 - 148 C

1-methyl-3-(m-nitrophenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 207 - 209 C

1-methyl-3-phen<y>1-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 208 - 210 C

1-methyl-3-(m-tolyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 159 - 162°C

1-methyl-3-(p-tolyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 237 - 24o C

1-methyl-3-(p-isopropylphenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 189 - 191C

1-methyl-3-([3-chloro-4-methylphenyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 189.5 - 190.5°C

1-methyl-3-(1-methylcyclopentyl)-6-dimethylamino-s-triazine-2,4-(1H,3H)-dione, m.p. 104 - 106°C

1-methyl-3-(2-methylcyclohexyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 125 - 126.5°C 1-methyl-3-(3-methylcyclohexyl)-6-dimethylamino-s-triazine, 2,4(1H,3H)-dione, m.p. 91 - 93°C

1-methyl-3-{2,4-dimethylcyclohexyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 120 - 122°c

1-methyl-3-(3,4-dimethylcyclohexyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, n^<5>1.5288

1-methyl-3-(2,6-dimethylcyclohexyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, n^<5> 1.5244

1-methyl-3-(2,3-dimethylcyclohexyl)-6-dimethyl-s-triazine-2,4(1H,3H)-dione, n^<5> 1.5283

1-methyl-3-(4-methoxycyclohexyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, n^<5>1.5305

1-methyl-3-cycloheptyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 116 - 118°C

1-methyl-1-3-cyclooctyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 133 - 133.5°C

1-methyl-3-(3-chlorocyclobutyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 16o°C

1-methyl-3-(4-isopropylcyclohexyl)-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 128 - 130 C

1-a hy1-3-isopropyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 63 - 65°C

1-propyl-3-isopropyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

n^<5> 1.5056

1-a hy1-3-cyclohexyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione,

n^<5> 1.5279

1-methyl-3-ethvl-6-methylamino-s-triazine-2,4(1H,3H)-dione, .

m.p. 206 - 207 C

1-methyl-3-(sec-butyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 199 - 200 C

1-methyl-3-(t-butyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 235 - 235.5 C 1-methyl-3-phenyl-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 293 - 296°C 1-methyl-3-(p-chlorophenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. >300 C 1-methyl-3-(3,4-dichlorophenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. >300 C

1-methyl-3-(o-chlorophenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. >300 C

l-methyl-3-(o-fluorophenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p.> 300 C

1-methyl-3-(m-nitrophenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p.> 300 C

1-methyl-3-(m-trifluoromethylphenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 241 - 243 C

1-methyl-3-isopropyl-6-methylamino-s-triazine-2,4(1H,3H9-dione,

m.p. 223 - 224°C

1-ethyl-3-isopropyl-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 240 - 241°C

1-propyl-3-isopropyl-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 166 - l67C

1-propyl-3-(p-chlorophenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 261 - 263°C

1-methyl-1-3-cyclohepty-1-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 273 - 274°C

1-methyl-3-cyclo<p>entyl-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 220 - 221.5 C

1-methyl-3-cyclooctyl-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p.> 300 C

1-methyl-3-(2-methylcyclohexyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 246 - 248.5°C

1-methyl-3-neopentyl-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 253 - 255 C

1-ethyl-3-cyclohexyl-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 226 - 227°C

1-methyl-3-(3-methylcyclohexyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 255 - 258°C

1-methyl-3-(m-tolyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 280 - 282°C 1-methyl-3-(3-chloro-p-tolyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 321.5 - 322.5 C

1-methyl-3-(2-methyl-5-chlorophenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 268 - 270°C

1-methyl-3-(3-pentyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 179 - 182°C

1-methyl-3-(3,4-dimethylcyclohexyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 295 - 298 C

1-methyl-3-(p-isopropylphenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 284 - 286C

1-methyl-3-(2,3-dimethylcyclohexyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 223 - 225°C

1-methyl-3-(2,4-dimethylcyclohexyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 214 - 216°C 1-methyl-3-(4-isopropylcyclohexyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 298 - 300°C

1-methyl-3-(3,5-dimethylcyclohexyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 250 - 252°C

1-methyl-3-(1-methylcyclopentyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 236 - 238 C

1-methyl-3-(3-chlorocyclobutyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 235 - 236 C

1-methyl-3-oethyl-6-methylamino-s-triazine-2,4 (1H,3H)-dione,

m.p. 89 - 91°C

1-methyl-3-(p-methylthiophenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 314 - 317°C

1-methyl-3-(2-methyl-4-chlorophenyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione, m.p. 293 - 295°C

1-methyl-3-(p-tolyl)-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 237 - 240°C

1-methyl-3-isobutyl-6-methylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 206 - 209°C 1-methyl-3-cyclohexyl-6-ethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 209 - 211°C

1-methyl-3-cyclohexyl-6-isopropylamino-s-triazine-2,4(1H,3H)-dione, m.p. 213 - 215°C 1-methyl-3-ethyl-6-(t-butylamino)-s-triazine-2,4 (1H,3H)-dione,

m.p. 182 - 183.5°C

1-methyl-3-isopropyl-6-isopropylamino-s-triazine-2,4(1H,3H)-dione, m.p. 181 - 184 C

1-methyl-3-isopropyl-6-propylamino-s-triazine-2,4(1H,3H)-dione, m.p. 158 - 161°C

1-methyl-3-isopropyl-6-(t-butylamino)-s-triazine-2,4(1H,3H)-dione, m.p. 185 - 186.5°C

1-methyl-1-3-isopropyl-6-propargylamino-s-triazine-2,4(1H,3H)-dione, n<*5> 1.5520

1-ethyl-1-3-isopropyl-6-ethylamino-s-triazine-2,4(1H,3H)-dione,

m.p. 170 - 173°C

1-methyl-3-isopropyl-6-diethylamino-s-triazine-2,4(1H,3H)-dione, n^<5> 1.5129

1-methyl-3-isopropyl-6-(N-butyl-N-methylamino)-s-triazine-2,4(1H,3H)-dione, n^<5>1.5182

1-methyl-3-cyclohexyl6-(N-methyl-N-propylamino)-s-triazine-2,4(1H,3H)-dione, r£<5> 1.5335

The compounds according to formula I are useful for controlling unwanted vegetation. They can be used at any time when general weed control is required, such as in industrial areas, in connection with railway lines and in areas adjacent to cultivation

fields in agricultural product areas.

The exact amount of 6-aminotriazinediones to be used in a given situation will vary according to the particular desired end result, the method used, the soil involved and the plant in question, the composition of the product, method of application, prevailing weather conditions, leaf density and the like factors. With so many variables at play, it is not possible to specify an application rate that is suitable for all situations. In general, it can be established that the agents according to the present invention are used in quantities corresponding to 0.5 - 25 kg/hectare of active ingredient.

The compounds according to formula I can be combined with other herbicides and are particularly useful in connection with "bromacil"

[3-(sec-butyl)-5-bromo-6-methyluracil], "diuron" [3-(3,4-dichloro-phenyl)-1,1-dimethylurea], paraquat (1,1•-dimethyl- 4,4'-bipyridinium ion), m-(3,3-dimethylureido)-phenyl-t-butylcarbamate, 4-amino-6-t-butyl-3-methylthio-as-triazin-5(4H)-one and s-triazines such as 2-chloro-4-ethylamino-6-isopropylamino-s-triazine, for controlling a broad spectrum of weeds.

The agents according to the invention can be formulated in various ways which are conventional for herbicides with similar physical properties. Useful formulations include wettable and soluble powders, suspensions and solutions in solvents and oils, aqueous dispersions, dusts, granules, pills and high concentration compositions. In general, these formulations essentially comprise 1 - 99% by weight of herbicidally active material (including at least one compound of formula I in a herbicidally effective amount) and at least one of a) approx. 0.1 - 20% by weight surfactant and b) 5 - 99% by weight of a solid or liquid diluent. More particularly, the different types of compositions will generally contain these components in the following approximate proportions.

The actual percentage ratios that can be obtained with a particular compound of formula I will depend on its physical properties.

The method of making and using such herbicidal preparations is described in the following US patents: 3,309,192, 3,235,357, 2,655,445, 2,863,752, 3,079,244, 2,891,855 and 2,642,354.

Many of the active compounds contained in the present agents exhibit an unusually high water solubility, up to several percent. This offers many advantages, for example when fighting scrub and other deep-rooted, perennial weeds. An example of a highly water-soluble active compound used in the present herbicides is 1-methyl-3-cyclohexyl-6-dimethyl-amino-s-triazine-2,4(1H,3H)-dione, which exhibits a solubility in water of approx. 3.2% at 25°C.

Example 1

Resolution

The ingredients are combined and mixed to give a solution that can be diluted with water for spraying.

Example 2

Wettable powder

1-methyl-3-cyclopentyl-6-dimethylamino-

These ingredients are carefully mixed and passed through a hammer mill to give particles substantially of a particle size below 10 µm.

The herbicidal activity of the agents according to the present invention was demonstrated in greenhouse experiments. In this experiment, seeds of Digitaria spp., Echinochloa crusgalli, Avena fatua, Cyperus rotundus, Cassia tora, Ipomoea spp., Brassica spp., Raphanus spp., Tagetes spp., Rumex crispus and Cyperus rotundus cuttings were planted in a growth medium and treated pre-emergence with two application rates (2.2 and 0.44 kg per ha) with chemicals dissolved in a non-phytotoxic solvent. At the same time, Sorghum halepense, with four leaves, Digitaria spp. and Echinochloa crusgalli with three leaves and Cyperus rotundus from cuttings with two leaves were treated post-emergence with a dose of 2.2 kg/ha. Treated plants and control plants were kept in the greenhouse for 16 days after which all species were compared with the control plants and visually assessed for the effect of the treatment. A quantitative grading was done on a scale from 0 to 10 where a grading of 10 means that the plant in question has been completely killed and a grading of 0 means that no damage could be detected.

A qualitative grading (type of damage) was also performed, with the letter "C" indicating chlorosis and the letter "G" indicating growth retardation. Grading in this test for some of the preferred compounds was as follows:

Biological data for terminal 6-aminotriazinediones Amount: 2.2 kg/ha, unless otherwise stated Column A - Echinochloa crusgalli - post-emergence Column B - Digitaria sp. - pre-emergence

Column C - Echinochloa crusgalli - pre-emergence Column D - Cassia - pre-emergence

Column E - Mustard - pre-emergence

o

St

In II

o In 3

CH3

Claims (2)

1. Herbicide, characterized in that it contains as active ingredient a compound with the general formula: where R1 means alkyl with 2-8 carbon atoms, alkenyl with 3-6 carbon atoms, cycloalkyl with 4-8 carbon atoms, cyclohexenyl, norbornyl, norbornylmethyl, trimethylcyclohexyl or tetramethyl-cyclohexyl, or the above-mentioned cycloalkyl groups substituted with one alkyl group with 2-4 carbon atoms , 1-2 methyl groups or 1-2 chlorine or bromine atoms, or R, is where Q is hydrogen, fluorine, chlorine, bromine, nitro or trifluoromethyl, Y is hydrogen, chlorine or methyl, R_ is hydrogen, methyl, ethyl or a cation comprising Na<+>, Li<+>, K , (Ca/2 ), ammonium or dimethylammonium, Rg is hydrogen or methyl, R^ is alkyl with 1-4 carbon atoms, and X is oxygen or sulphur, with the proviso that when X is sulfur, neither R nor R„ 2 3 is hydrogen. 2. Means according to claim 1, characterized in that it contains as active compound 1-methyl-1-3-cyclohexyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione.