The present invention relates to certain new 3-alkenylmercapto-, 
3-alkinylmercapto-, 3-alkenylamino- and 
3-alkinylamino-4-amino-6-tert.-butyl-1,2,4-triazin-5-ones, to processes 
for their production, and to their use as herbicides, in particular as 
selective herbicides. 
It has already been disclosed that substituted 1,2,4-triazin-5-ones, such 
as, for example, 
4-amino-3-methylmercapto-6-tert.-butyl-1,2,4-triazin-5-one, can be used as 
herbicides (see, for example, German Patent Specification No. 1,795,784 
and U.S. Patent Specification No. 3,671,523). In certain crops, however, 
selective use of the previously known triazinones is not possible since 
damage may also occur to certain crop plants, owing to the high herbicidal 
power of all members of this group of substances; accordingly, the 
previously known triazinones are not sufficiently tolerated by various 
crop plants. 
The present invention now provides, as new compounds, the 
3-alken(in)yl-mercapto(amino)-4-amino-6-tert.-butyl-1,2,4-triazin-5-ones 
of the general formula 
##STR2## 
in which A represents sulphur or a radical of the general formula 
--NR.sup.2 --, 
R.sup.2 represents a hydrogen atom or an alkyl group, 
R.sup.1 represents an alkenyl or alkinyl group, 
X represents a halogen atom or an alkoxy group and 
Y represents a hydrogen or halogen atom or an alkoxy group. 
The present invention further relates to a process for the production of a 
compound of the present invention, characterized in that 
(a) a 4-amino-3-mercapto-6-tert.-butyl-1,2,4-triazin-5-one of the formula 
##STR3## 
in which X and Y have the meanings given above, is reacted with a halide 
of the general formula 
EQU Hal--R.sup.1 (III) 
in which 
R.sup.1 has the meaning given above, and 
Hal represents a halogen atom, in the presence of a base and, if 
appropriate, in the presence of a diluent, or 
(b) a 3-alkylmercapto-4-amino-6-tert.-butyl-1,2,4-triazin-5-one of the 
general formula 
##STR4## 
in which 
X and Y have the meaning given above, and 
R.sup.3 represents an alkyl group, is reacted with an amine of the general 
formula 
##STR5## 
in which 
R.sup.1 and R.sup.2 have the meanings given above, in the presence of a 
diluent and, if appropriate, in the presence of a lower aliphatic 
carboxylic acid. 
In addition, it has been found that the 
3-alken(in)yl-mercapto(amino)-4-amino-6-tert.-butyl-1,2,4-triazin-5-ones 
of the formula (I) possess good herbicidal properties, in particular 
selective herbicidal properties. 
Compared to the known 
4-amino-3-methylmercapto-6-tert.-butyl-1,2,4-triazin-5-one, which is a 
similar compound chemically and in terms of its action, the compounds 
according to the invention surprisingly exhibit substantially better 
toleration by important crop plants, such as, in particular, wheat, oats 
and corn coupled with an equally good general herbicidal action. The 
active compounds according to the invention thus represent a substantial 
enrichment of herbicidal means, in particular of the selective chemical 
combating of weeds. 
Preferred compounds according to the present invention are those in which 
A represents sulphur or a radical of the general formula --NR.sup.2 --, 
wherein 
R.sup.2 represents a hydrogen atom or a straight-chain or branched alkyl 
group having 1 to 4 carbon atoms; 
R.sup.1 represents a straight-chain or branched alkenyl group having 3 to 6 
carbon atoms or a straight-chain or branched alkinyl group having 3 to 6 
carbon atoms; 
X represents a fluorine, chlorine or bromine atom or a straight-chain or 
branched alkoxy group having 1to 4 carbon atoms; and 
Y represents a hydrogen, fluorine, chlorine or bromine atom, or a 
straight-chain or branched alkoxy group having 1 to 4 carbon atoms. 
Particularly preferred compounds of the present invention are those in 
which 
A represents sulphur or a radical of the general formula --NR.sup.2 --, 
wherein 
R.sup.2 represents a hydrogen atom or a methyl or ethyl group; 
R.sup.1 represents a radical selected from --CH.sub.2 --CH.dbd.CH.sub.2, 
--CH.sub.2 --CH.dbd.CH--CH.sub.3, --CH.sub.2 --C(CH.sub.3).dbd.CH.sub.2, 
--CH(CH.sub.3)--CH.dbd.CH.sub.2, --C(CH.sub.3).sub.2 --CH.dbd.CH.sub.2, 
--CH.sub.2 C.vertline.CH, --CH(CH.sub.3)--C.vertline.CH and 
--C(CH.sub.3).sub.2 --C.vertline.CH; 
X represents a fluorine or chlorine atom or a methoxy, ethoxy or isopropoxy 
group; and 
Y represents a hydrogen, fluorine or chlorine atom or a methoxy, ethoxy or 
isopropoxy group. 
If, for example, 
4-amino-6-chloro-tert.-butyl-3-mercapto-1,2,4-triazin-5-one and propargyl 
bromide are used as starting materials, the course of the reaction 
according to reaction variant (a) may be represented by the following 
equation: 
##STR6## 
If, for example, 
4-amino-6-fluoro-tert.-butyl-3-methylthio-1,2,4-triazin-5-one and 
allylamine are used as starting materials, the course of the reaction 
according to reaction variant (b) may be represented by the following 
equation: 
##STR7## 
Preferred 4-amino-3-mercapto-6-tert.-butyl-1,2,4-triazin-5-ones of formula 
(II) to be used as starting materials for reaction variant (a) are those 
in which X and Y represent the radicals which have already been mentioned 
for these substituents in connection with the desciption of the preferred 
and particularly preferred compounds according to the invention. 
The 4-amino-3-mercapto-6-tert.-butyl-1,2,4-triazin-5-ones of the formula 
(II) are not yet known; however, they form the subject of United States 
patent applications Ser. Nos. 299,919, filed Sept. 8, 1981, now U.S. Pat. 
Nos. 4,386,953 and 411,745, filed Aug. 26, 1982, now pending. They are 
obtained when, in a first stage, a pivaloyl cyanide of the general formula 
##STR8## 
in which 
X and Y have the meanings given above, (.alpha.) is reacted with an 
inorganic acid (such as hydrohalic acid) at a temperature between 
0.degree. and 40.degree. C., if appropriate in the presence of a liquid 
carboxylic acid (such as acetic acid) as the solvent, or (.beta.) is added 
onto a carbonium ion which is formed from an olefin (such as isobutylene) 
or a tertiary alcohol (such as tert.-butanol) and a strong acid (such as 
sulphuric acid) and the subjected to hydrolysis; and the resulting 
trimethylpyruvic acid amide of the general formula 
##STR9## 
in which 
X and Y have the meanings given above, and 
R represents a hydrogen atom (obtainable according to variant (.alpha.), or 
an alkyl group, especially a tert.-butyl group, (obtainable according to 
variant (.beta.), 
is reacted in a second stage, in a manner which is in itself known, either 
directly in the solution obtained or after intermediate isolation, if 
appropriate after prior hydrolysis to the free, substituted 
trimethylpyruvic acid of the general formula 
##STR10## 
in which 
X and Y have the meanings given above, with a thiocarbohydrazide of the 
formula 
##STR11## 
in aqueous or in aqueous-acidic solution (such as a solution containing a 
hydrohalic acid), if appropriate in the presence of an organic solvent 
(such as, in particular, dimethylformamide) at a temperature between 
0.degree. and 100.degree. C. 
The pivaloyl cyanides of the formula (VI) are not yet known. They, also 
form the subject of our above-mentioned patent applications. The pivaloyl 
cyanides of the formula (VI) can be obtained by reacting the corresponding 
pivaloyl halides or pivaloyl anhydrides of the formulae IXa and IXb, 
respectively, 
##STR12## 
in which 
X and Y have the meanings given above, and 
Hal represents a halogen atom, preferably a chlorine or bromine atom, 
with trimethylsilyl cyanide, if appropriate in the presence of an inert 
organic solvent (such as acetonitrile) at a temperature between 80.degree. 
and 110.degree. C. The trimethylsilyl cyanide, (CH.sub.3).sub.3 Si-CN, is 
known (see, for example, Synthesis 1979, pages 522 and 523). 
The pivaloyl halides and pivaloyl anhydrides of the formulae (IXa) and 
(IXb) are known, or can be prepared by known processes: 
Preferred halides of formula (III) additionally to be used as starting 
materials for reaction variant (a) are those in which R.sup.1 represents 
the radicals which have already been mentioned for this substituent in 
connection with the preferred and particularly preferred compound 
according to the invention and Hal represents a chlorine or bromine atom. 
The halides of the formula (III) are generally known compounds of organic 
chemistry. 
Preferred 3-alkylmercapto-4-amino-6-tert.-butyl-1,2,4-triazin-5-ones of 
formula (IV) to be used as starting materials for reaction variant (b) are 
those in which X and Y represent the radicals which have already been 
mentioned in these substituents in connection with the description of the 
preferred and particularly preferred compounds according to the invention, 
and R.sup.3 represents an alkyl group having 1 to 4 carbon atoms, such as, 
especially, a methyl group. 
The 3-alkylmercapto-4-amino-6-tert.-butyl-1,2,4-triazin-5-ones of the 
formula (IV) are not yet known. They, also, form the subject of the 
above-mentioned patent applications, and are obtained by reacting a 
4-amino-3-mercapto-6-tert.-butyl-1,2,4-triazin-5-one of the formula (II) 
with an alkyl halide (such as methyl iodide or methyl bromide) according 
to reaction variant (a). 
Preferred amines of formula (V) additionally to be used as starting 
materials for reaction variant (b) are those in which R.sup.1 and R.sup.2 
represent the radicals which have already been mentioned for these 
substituents in connection with the description of the preferred and 
particularly preferred compounds according to the invention. 
The amines of the formula (V) are generally known compounds of organic 
chemistry. 
Suitable diluents for reaction variant (a) according to the present 
invention are protic and aprotic solvents. These include, for example, 
water, alcohols, carboxylic acids, acetone, acetonitrile, 
dimethylformamide, dimethylsulphoxide and toluene. 
The reaction variant (a) according to the invention is carried out in the 
presence of a base. These include any of the organic and, especially, 
inorganic bases which can customarily be used (such as sodium hydroxide, 
potassium hydroxide, sodium carbonate and potassium carbonate). 
In carrying out reaction variant (a) according to the invention, the 
reaction temperatures can be varied within a relatively wide range. In 
general, the reaction is carried out at a temperature between 0.degree. 
and 120.degree. C., preferably between 20.degree. and 100.degree. C. 
In carrying out the process according to the invention, 1 to 2 mols of the 
halide of the formula (III) are preferably employed per mol of the 
compound of the formula (II). The end products are isolated in a generally 
customary manner. 
According to a preferred embodiment of reaction variant (a) according to 
the invention, the reaction is carried out in a two-phase system (for 
example, aqueous sodium hydroxide solution or potassium hydroxide 
solution/toluene or methylene chloride) with the addition of 0.01-1 mol of 
a phase transfer catalyst (such as an ammonium compound or phosphonium 
compound) per mol of the compound of formula (II). 
Suitable diluents for reaction variant (b) according to the invention are 
any of the inert organic solvents. These include hydrocarbons (such as 
toluene and xylene), chlorinated aromiatic hydrocarbons (such as 
chlorobenzene, 1,2-dichlorobenzene and 1,2,4-trichlorobenzene), ethers 
(such as tetrahydrofuran and dioxane), alcohols (such as methanol, 
ethanol, propanol and isopropanol), amides (such as N,N-dimethylformamide 
and tetramethylurea) or sulphoxides (such as dimethylsulphoxide). 
Isopropanol is preferably used for the reaction. 
In carrying out reaction variant (b) according to the invention, the 
reaction temperatures can be varied within a relatively wide range. In 
general, the reaction is carried out at a temperature between 60.degree. 
and 90.degree. C. 
The reaction according to reaction variant (b) can be carried out under 
atmospheric pressure as well as under elevated pressures. 
A particularly advantageous embodiment of reaction variant (b) comprises 
carrying out the reaction in the presence of at least an equimolar amount 
of a C.sub.1 to C.sub.6 aliphatic carboxylic acid. Acetic acid is 
preferably used for this purpose. This process permits the use of a 
relatively small excess of amine. In this embodiment, the reaction rate 
can be increased by the addition of a catalytic amount of an organic 
sulphonic acid. p-Toluene-sulphonic acid is preferably used for this 
purpose. 
In carrying out reaction variant (b) according to the invention, 1 to 2 
mols of a lower aliphatic carboxylic acid, 0.01 to 0.05 mol of an organic 
sulphonic acid and 1 to 5 mols of the amine of the formula (V) are 
advantageously employed per mol of the 3-alkylmercaptotriazinone of the 
formula (IV), and the mixture is heated until the splitting off of the 
mercaptan is complete, and is then worked up. 
The active compounds according to the invention influence plant growth and 
can therefore be used as defoliants, desiccants, agents for destroying 
broad-leaved plants, germination inhibitors and, especially, as 
weed-killers. By "weeds" in the broadest sense there are meant plants 
growing in places where they are not desired. 
Whether the compounds according to the invention act as total herbicides or 
selective herbicides depends essentially on the amount used. 
The active compounds according to the present invention may be used, for 
example, to combat the following plants: 
dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, 
Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, 
Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, 
Cirsium, Carduus, Sonchus, Rorippa, Rotala, Lindernia, Lamium, Veronica, 
Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea and Solanum; 
and 
monocotyledon weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, 
Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, 
Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, 
Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, 
Dactyloctenium, Agrostis, Alopecurus and Apera. 
The active compounds according to the present invention may be used, for 
example, as selective herbicides in the following cultures: 
dicotyledon cultures of the genera Gossypium, Glycine, Beta, Daucus, 
Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, 
Arachis, Brassica, Lactuca, Cucumis and Cucurbita; and 
monocotyledon cultures of the genera Oryza, Zea, Triticum, Hordeum, Avena, 
Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium. 
However, the use of the active compounds according to the invention is in 
no way restricted to these genera but also embraces other plants, in the 
same way. 
Depending on the concentrations, the compounds can be used for the total 
combating of weeds, for example on industrial terrain and railway tracks 
and on paths and squares with or without trees. Equally, the compounds can 
be employed for combating weeds in perennial cultures, for example 
afforestations, decorative tree plantings, orchards, vineyards, citrus 
groves, not orchards, banana plantations, coffee plantations, tea 
plantations, rubber plantations, oil palm plantations, cacao plantations, 
soft fruit plantings and hopfields, and for the selective combating of 
weeds in annual cultures. 
In addition to showing a very good general herbicidal action, the active 
compounds according to the invention are well tolerated by crop plants. 
Thus, it is possible selectively to combat important graminaceous weeds in 
important crop plants, for example, in wheat, oats and corn. 
The active compounds can be converted to the customary formulations, such 
as solutions, emulsions, wettable powders, suspensions, powders, dusting 
agents, pastes, soluble powders, granules, suspension-emulsion 
concentrates, natural and synthetic materials impregnated with active 
compound, and very fine capsules in polymeric substances. 
These formulations may be produced in known manner, for example by mixing 
the active compounds with extenders, that is to say liquid or solid 
diluents or carriers, optionally with the use of surface-active agents, 
that is to say emulsifying agents and/or dispersing agents and/or 
foam-forming agents. In the case of the use of water as an extender, 
organic solvents can, for example, also be used as auxiliary solvents. 
As liquid diluents or carriers, especially solvents, there are suitable in 
the main, aromatic hydrocarbons, such as xylene, toluene or alkyl 
naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, 
such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic 
or alicyclic hydrocarbons, such as cyclohexane or paraffins, for example 
mineral oil fractions, alcohols, such as butanol or glycol as well as 
their ethers and esters, ketones, such as acetone, methyl ethyl ketone, 
methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such 
as dimethylformamide and dimethylsulphoxide, as well as water. 
As solid carriers there may be used ground natural minerals, such as 
kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or 
diatomaceous earth, and ground synthetic minerals, such as 
highly-dispersed silicic acid, alumina and silicates. As solid carriers 
for granules there may be used crushed and fractionated natural rocks such 
as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic 
granules of inorganic and organic meals, and granules of organic material 
such as sawdust, coconut shells, corn cobs and tobacco stalks. 
As emulsifying and/or foam-forming agents there may be used non-ionic and 
anionic emulsifiers, such as polyoxyethylene-fatty acid esters, 
polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol 
ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as 
albumin hydrolysis products. Dispersing agents include, for example, 
lignin sulphite waste liquors and methylcellulose. 
Adhesives such as carboxymethylcellulose and natural and synthetic polymers 
in the form of powders, granules or latices, such as gum arabic, polyvinyl 
alcohol and polyvinyl acetate, can be used in the formulations. 
It is possible to use colorants such as inorganic pigments, for example 
iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such 
as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, 
and trace nutrients, such as salts of iron, manganese, boron, copper, 
cobalt, molybdenum and zinc. 
The formulations in general contain from 0.1 to 95 percent by weight of 
active compound, preferably from 0.5 to 90 percent by weight. 
The active compounds according to the invention, as such or in the form of 
their formulations, can also be used, for combating weeds, as mixtures 
with known herbicides, finished formulations or tank mixing being 
possible. Mixtures with other known active compounds, such as fungicides, 
insecticides, acaricides, nematicides, bird repellants, growth factors, 
plant nutrients and agents which improve soil structure, are also 
possible. 
The active compounds can be used as such, in the form of their formulations 
or in the use forms prepared therefrom by further dilution, such as 
ready-to-use solutions, suspensions, emulsions, powders, pastes and 
granules. They are used in the customary manner, for example by watering, 
spraying, atomizing, scattering or dusting. 
When used as herbicides, the active compounds according to the invention 
can be applied either before or after emergence of the plants. They can 
also be incorporated into the soil before sowing. 
The amount of active compound used can vary within a substantial range. It 
depends essentially on the nature of the desired effect. In general, the 
amounts used are between 0.1 and 10 kg/ha, preferably between 0.2 and 6 
kg/ha. 
The present invention also provides herbicidal compositions containing as 
active ingredient a compound of the present invention in admixture with a 
solid diluent or carrier or in admixture with a liquid diluent or carrier 
containing a surface-active agent. 
The present invention also provides a method of combating weeds which 
comprises applying to the weeds, or to a habitat thereof, a compound of 
the present invention alone or in the form of a composition containing as 
active ingredient a compound of the present invention in admixture with a 
diluent or carrier. 
The present invention further provides crops protected from damage by weeds 
by being grown in areas in which immediately prior to and/or during the 
time of the growing a compound of the present invention was applied alone 
or in admixture with a diluent or carrier. 
It will be seen that the usual methods of providing a harvested crop may be 
improved by the present invention. 
The examples which follows serve to illustrate the invention further.

PREATIVE EXAMPLES 
EXAMPLE 1 
##STR13## 
(Reaction variant (a)) 
18.6 g (80% stength solution in toluene=0.125 mol) of propargyl bromide and 
0.5 g of pentyltributylphosphonium bromide were added to a solution of 
23.5 g (0.1 mol) of 
4-amino-6-chloro-tert.-butyl-3-mercapto-1,2,4-triazin-5-one and 4.4 g of 
sodium hydroxide in 40 ml of water. The reaction mixture was stirred for 
about 20 hours at room temperature, 100 ml of toluene were then added, and 
the mixture was filtered. The filtrate was washed with 100 ml of water, 
with 100 ml of 1 N sodium hydroxide solution and again with water. The 
organic phase was dried over sodium sulphate, filtered and concentrated. 
The oily residue was brought to crystallization by trituration in 
diisopropyl ether, and the product was recrystallized from ethyl 
acetate/petroleum ether. 13.8 g (57.5% of theory) of 
4-amino-6-chloro-tert.-butyl-3-propargylthio-1,2,4-triazin-5-one of 
melting point 107.degree.-108.degree. C. were obtained. 
Preparation of the starting material 
##STR14## 
2.31 kg (15.88 mols) of chloropivaloyl cyanide were added to 9 liters of a 
solution of hydrogen bromide in glacial acetic acid (33% strength) at room 
temperature, while stirring. The mixture was stirred for a further 4 
hours at room temperature. Thereafter, 288 ml (15.88 mols) of water were 
added at 7.degree. to 10.degree. C. (exothermic reaction, approximately 
37.degree. C.), and the mixture was stirred for a further 3 hours at room 
temperature. The reaction solution was thereafter introduced into a 
mixture of 2.03 kg of thiocarbohydrazide and 15.9 liters of 1 N 
hydrochloric acid at 7.degree. to 10.degree. C. (strongly exothermic 
reaction). This reaction mixture was stirred further for 2 hours at 
7.degree. to 10.degree. C. and for 14 hours at room temperature. 
Thereafter, the precipitated crystals were filtered off, washed with water 
and dried. 2,995 g (80.4% of theory) of crude 
4-amino-6-chloro-tert.-butyl-3-mercapto-1,2,4-triazin-5-one of melting 
ponit 202.degree. to 208.degree. C. were obtained. 
##STR15## 
8,300 g (49.5 mols) of 92.5% strength .beta.-chloropivaloyl chloride were 
warmed to 100.degree. C., and 4,950 g (50 mols) of trimethylsilyl cyanide 
were added in the course of about 2 hours. The trimethylsilyl chloride 
formed was distilled off simultaneously. After the end of the addition, 
the temperature was slowly increased to 140.degree. C., and the mixture 
was stirred for about 1.5 hours at this temperature. The reaction mixture 
was then distilled in vacuo. 7,500 g of .beta.-chloropivaloyl cyanide of 
boiling point 62.degree.-65.degree. C./16 mbar were obtained. 
EXAMPLE 2 
##STR16## 
(Reaction variant (a)) 
26.6 g (0.22 mol) of allyl bromide were added to a solution of 43.6 g (0.2 
mol) of 4-amino-6-fluoro-tert.-butyl-3-mercapto-1,2,4-triazin-5-one in 200 
ml of 1 N sodium hydroxide solution at room temperature. The reaction 
mixture was stirred for approximately 20 hours at room temperature, the 
organic phase was then taken up in chloroform, and the solution was washed 
with three times 150 ml of 0.1 N sodium hydroxide solution, dried over 
sodium sulphate, filtered and concentrated. The oily residue was degassed 
at 50.degree. C./0.05 mbar, and recrystallized from ethyl 
acetate/petroleum ether. 20.8 g (40% of theory) of 
3-allylthio-4-amino-6-fluoro-tert.-butyl-1,2,4-triazin-5-one of melting 
point 75.degree. to 74.degree. C. were obtained. 
EXAMPLE 3 
##STR17## 
(Reaction variant (b)) 
11.06 g (0.05 mol) of 
4-amino-6-fluoro-tert.-butyl-3-methylthio-1,2,4-triazin-5-one and 14.3 g 
(0.25 mol) of allylamine were added to 6 g (0.1 mol) of glacial acetic 
acid in 250 ml of isopropanol, and the mixture was stirred while cooling 
with ice. Thereafter, the reaction mixture was heated under reflux for 
about 40 hours. The mixture was allowed to cool, and concentrated, the 
residue was taken up in methylene chloride, and the solution was washed 
with 200 ml of 1 N sodium hydroxide solution and with 200 ml of water, 
dried over sodium sulphate, filtered and concentrated. The oily residue 
was crystallized by trituration with diisopropyl ether. After 
recrystallization from ethyl acetate/petroleum ether, 4.9 g (41% of 
theory) of 3-allylamino-4-amino-6-fluoro-tert.-butyl-1,2,4-triazin-5-one 
of melting point 100.degree.-104.degree. C. where obtained. 
Preparation of the starting material 
##STR18## 
Using fluoropivaloyl cyanide as a starting material crude 
4-amino-6-fluoro-tert.-butyl-3-mercapto-1,2,4-triazin-5-one was first 
obtained, in a yield of 80%, by the method described in Example 1. 3,347.4 
g (12 mols) of the 
4-amino-6-fluoro-tert.-butyl-3-mercapto-1,2,4-triazin-5-one obtained in 
this manner were dissolved in 15 liters of 1 N sodium hydroxide solution. 
After the product had completely dissolved, 1,873.6 g of methyl iodide 
were added dropwise at 7.degree. to 10.degree. C. After the end of the 
addition, the mixture was stirred further for 2 hours at 7.degree. to 
10.degree. and overnight at room temperature. Thereafter, the solid 
obtained was filtered off under suction, washed with water and dried. 
2,285 g (65% of theory) of 
4-amino-6-fluoro-tert.-butyl-3-methylthio-1,2,4-triazin-5-one of melting 
point 121-122.degree. C. were obtained. 
The compounds of the general formula 
##STR19## 
which are listed in Table 1 below were obtained in an analogous manner and 
according to the processes according to the invention: 
__________________________________________________________________________ 
Example Melting point 
No. X Y A R.sup.1 (.degree.C.) or n.sub.D.sup.20 
__________________________________________________________________________ 
4 F H S --CH.sub.2 --CH.dbd.CH--CH.sub.3 
1.566 
5 F H S --CH.sub.2 --C.tbd.CH 
94-95 
6 Cl H S --CH.sub.2 --CH.dbd.CH.sub.2 
65-66 
7 Cl H S --CH.sub.2 --CH.dbd.CH--CH.sub.3 
1.577 
8 Cl H NH --CH.sub.2 --CH.dbd.CH.sub.2 
82-85 
9 F F S --CH.sub.2 --CH.dbd.CH--CH.sub.3 
1.555 
10 Cl H NH --CH.sub.2 --C.tbd.CH 
116-17 
11 F H NH --CH.sub.2 --C.tbd.CH 
129-31 
12 F H N(CH.sub.3) 
--CH.sub.2 --C.tbd.CH 
viscous oil 
13 F H S --CH.sub.2 --CH.dbd.CH.sub.2 
1.550 
14 F H S --CH.sub.2 --C.tbd.CH 
68-69 
15 Cl H N(CH.sub.3) 
--CH.sub.2 --C.tbd.CH 
1.562 
16 F F NH --CH.sub.2 --CH.dbd.CH.sub.2 
101-102 
17 H.sub.5 C.sub.2 O-- 
H S --CH.sub.2 --C.tbd.CH 
69-70 
18 H.sub.3 CO-- 
H S --CH.sub.2 --C.tbd.CH 
133-34 
19 H.sub.5 C.sub.2 O-- 
H S --CH.sub.2 --CH.dbd.CH.sub.2 
54-56 
20 H.sub.5 C.sub.2 O-- 
H NH --CH.sub.2 --CH.dbd.CH.sub.2 
1.536 
21 H.sub.5 C.sub.2 O-- 
H S --CH.sub.2 --CH.dbd.CH--CH.sub.3 
1.557 
__________________________________________________________________________ 
The herbicidal activity of the compounds of this invention is illustrated 
by the following biotest examples. 
In these examples the compounds according to the present invention are each 
identified by the number (given in brackets) of the corresponding 
preparative example. 
EXAMPLE A 
Pre-emergence test 
Solvent: 5 parts by weight of acetone 
Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound was mixed with the stated amount of solvent, the stated 
amount of emulsifier was added and the concentrate was diluted with water 
to the desired concentration. 
Seeds of the test plants were sown in normal soil and, after 24 hours, 
watered with the preparation of the active compound. It was expedient to 
keep constant the amount of water per unit area. The concentration of the 
active compound in the preparation was of no importance, only the amount 
of active compound applied per unit area being decisive. After three 
weeks, the degree of damage to the plants was rated in % damage in 
comparison to the development of the untreated control. The figures 
denoted: 
0%=no action (like untreated control) 
100%=total destruction 
In this test the compounds (1), (3), (5) and (8), for example, showed a 
very good selectivity in wheat and corn, coupled with good general 
activity. 
EXAMPLE B 
Post-emergence test 
Solvent: 5 parts by weight of acetone 
Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound was mixed with the stated amount of solvent, the stated 
amount of emulsifier was added and the concentrate was diluted with water 
to the desired concentration. 
Test plants which had a height of 5 to 15 cm were sprayed with the 
preparation of the active compound in such a way as to apply the amounts 
of active compound per unit area which were prescribed. The concentration 
of the sprayed liquor was so chosen that the amounts of active compound 
were applied in 2,000 liters of water/ha. After three weeks, the degree of 
damage to the plants was rated in % damage in comparison to the 
development of the untreated control. The figures denoted: 
0%=no action (like untreated control) 
100%=total destruction 
In this test the compounds (1), (3) and (5), for example, showed a very 
good selectivity in oats, wheat and maize, coupled with good general 
activity. 
It will be understood that the specification and examples are illustrative 
but not limitative of the present invention and that other embodiments 
within the spirit and scope of the invention will suggest themselves to 
those skilled in the art.