A herbicidal and fungicidal composition which comprises as an active ingredient a pyridyltriazinone compound of the formula: ##STR1## wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxycarbonylmethyl group whose alkoxy has 1 to 3 carbon atoms or a phenyl group.

The present invention relates to a herbicidal and fungicidal composition. 
More particularly, it relates to a non-medical (i.e. agricultural or 
industrial) composition for herbicidal and fungicidal use, and an active 
ingredient to be used therein and its preparation. 
The active ingredient in the herbicidal and fungicidal composition of the 
invention is a pyridyltriazinone compound of the formula: 
##STR2## 
wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms 
(e.g. methyl, ethyl, propyl, butyl, pentyl), an alkoxycarbonylmethyl group 
whose alkoxy has 1 to 3 carbon atoms (e.g. methoxycarbonylmethyl, 
ethoxycarbonylmethyl, propoxycarbonylmethyl) or a phenyl group. 
It has now been found the pyridyltriazinone compounds (I) exhibit excellent 
herbicidal and fungicidal activities. It may be noted that their 
herbicidal activity is much stronger than known 1,2,4-triazinon-5-one 
derivatives. It may be also noted that their fungicidal activity is 
effective against a wide variety of phytopathogenic fungi. It may be 
further noted that they exert a notable antimicrobial activity against 
various fungi and bacteria parasitic on industrial articles and products. 
Advantageously, the toxicity of the pyridyltriazinone compounds (I) to 
mammals and fishes is remarkably low. 
Some specific examples of the pyridyltriazinone compounds (I) are shown in 
the following table: 
Table 1 
______________________________________ 
Com- 
pound Physical 
No. Chemical structure constant 
______________________________________ 
##STR3## M.P. 138- 139.degree. C. 
2 
##STR4## M.P. 151- 151.5.degree. C. 
3 
##STR5## M.P. 162- 164.degree. C. 
4 
##STR6## M.P. 167- 168.degree. C. 
______________________________________ 
The pyridyltriazinone compound (I) may be produced, for instance, by 
reacting picoline amidrazone of the formula: 
##STR7## 
with a haloacetic acid or its ester of the formula: 
##STR8## 
wherein X is a halogen atom (e.g. chlorine, bromine, iodine), R' is a 
hydrogen atom or an alkyl group having 1 to 3 carbon atoms (e.g. methyl, 
ethyl, propyl) and R is as defined above. The reaction may be carried out 
in an inert solvent (e.g. benzene, chlorobenzene, toluene, xylene, 
ligroin, hexane, isopropyl ether, tetrahydrofuran, dioxane, chloroform, 
methanol, ethanol, isopropanol, water), preferably in the presence of an 
acid-eliminating agent (e.g. sodium hydroxide, potassium hydroxide, sodium 
methoxide, sodium ethoxide, pyridine, triethylamine, dimethylaniline, 
diethylaniline) at a wide range of temperature from cooling to heating. 
The produced pyridyltriazinone compound (I) may be recovered from the 
reaction mixture by a conventional separation procedure, optionally 
followed by purification. 
A typical example of the preparation process is as follows: 
In a 200 ml four-necked flask were charged 13.6 g of picoline amidrazone, 
15 g of triethylamine and 100 ml of benzene, and the mixture was cooled 
below 10.degree. C. while stirring. After the dropwise addition of 18.4 g 
of ethyl bromoacetate at 10.degree. to 15.degree. C. while stirring, the 
resulting mixture was heated under reflux for 2 hours. The reaction 
mixture was cooled, and the deposited triethylamine hydrobromide was 
removed by filtration. Removal of the solvent under reduced pressure gave 
12.9 g of 3-(2-pyridyl)-1,4,5,6-tetrahydro-1,2,4-triazin-5-one as white 
crystals. M.P. 138.degree.-139.degree. C. Anal. Calcd. for C.sub.8 H.sub.8 
N.sub.4 O: C, 54.55%; H, 4.55%; N, 31.82%. Found: C, 54.38%; H, 4.63%, N, 
32.01%. 
Other pyridyltriazinone compounds (I) may be prepared in the same procedure 
as outlined above. 
The pyridyltriazinone compounds (I) show a strong herbicidal activity on 
grassy weeds such as barnyard grass (Echinochloa crus-galli) and large 
crabgrass (Digitaria sanguinalis), and weeds in upland and paddy fields 
such as nutsedge sp. (Cyperus difforuds), redroot pigweed (Amaranthus 
retroflexus), common lambsquarter (Chenopodium album), chickweed 
(Stellaria media) and toothcup (Rotala indica Koehne). They exert their 
herbicidal effect on foliage treatment and also on pre-emergence 
treatment. Their selectivity is so remarkable that any appreciable harmful 
effect is not seen on many crops such as rice plant, wheat, radish, 
soybean, cotton, beet, corn and rapeseed. Therefore, the pyridyltriazinone 
compounds (I) are useful as herbicides for fields, paddy rice fields, 
orchards, turfs, pasture lands, woods and forests, non-crop lands, etc. 
When the pyridyltriazinone compounds (I) are used as herbicides, they may 
be applied as such or in any of the preparation forms such as dusts, 
granules, fine granules, wettable powders and emulsifiable concentrates. 
These preparations can be produced in combination with solid carriers and 
liquid carriers. The solid carriers include, for example, talc, bentonite, 
clay, kaolin, diatomaceous earth, vermiculite, slaked lime, etc., and the 
liquid carriers include, for example, benzene, alcohols, acetone, xylene, 
methylnaphthalene, dioxane, cyclohexanone, etc. In the practical 
application, they may be applied in combination with surfactants for 
agricultural use, for example, spreaders in order to promote and ensure 
the herbicidal activity, or may be applied in combination with 
agricultural chemicals such as fungicides, insecticides and fertilizers. 
They may be also used together with any other herbicides. 
In general, the pyridyltriazinone compounds (I) may be contained in the 
compositions for herbicidal use at a concentration of from 0.1 to 95% by 
weight. 
Very often, the pyridyltriazinone compounds (I) are formulated as 
concentrated compositions which are applied either to the soil or the 
foliage in the form of water dispersions or emulsions containing the same 
in the range of from 0.1 to 5 % by weight. Water-dispersible or 
emulsifiable compositions are either solids usually known as wettable 
powders, or liquids usually known as emulsifiable concentrates. These 
concentrated compositions may be used in the range: 
______________________________________ 
% by weight 
Pyridyltriazinone 10 - 80 
compound (I) 
Surfactant 3 - 10 
Inert carrier 87 - 10 
______________________________________ 
Wettable powders comprise an intimate, finely-divided mixture of the 
pyridyltriazinone compounds (I), an inert carrier and surfactants. The 
concentration of the compound is usually from 10 to 90 % by weight. The 
inert carrier is usually chosen from among attapulgite clays, kaolin 
clays, montmorillonite clays, diatomaceous earths and purified silicates. 
Effective surfactants, comprising from 0.5 to 10 % by weight of the 
wettable powder, are found among sulfonated lignins, condensed 
naphthalenesulfonates, naphthalenesulfonates, alkylbenzenesulfonates, 
alkyl sulfates and nonionic surfactants such as ethylene oxide adducts of 
phenol. 
Typical emulsifiable concentrates of the pyridyltriazinone compounds (I) 
comprise a convenient concentration of the same, such as from about 100 to 
500 g per liter of liquid, dissolved in an inert carrier which is a 
mixture of a water-immiscible solvent and emulsifiers. Useful organic 
solvents include aromatics, especially xylenes, and petroleum fractions, 
especially the high-boiling naphthalenic and olefinic portions of 
petroleum. Many other organic solvents may also be used such as terpenic 
solvents, and complex alcohols such as 2-ethoxyethanol. Suitable 
emulsifiers for emulsifiable concentrates are chosen from the same types 
of surfactants as are used for wettable powders. 
When the pyridyltriazinone compounds (I) are to be applied to the soil, as 
for a pre-emergence application, it is convenient to use a granular 
formulation. Such a formulation typically comprises the compound dispersed 
on a granular inert carrier such as coarsely ground clay. The particle 
size of the granules usually ranges from about 0.1 to 3 mm. The usual 
formulation process for granules comprises dissolving the compound in an 
inexpensive solvent and applying the solution to the carrier in an 
appropriate solid mixer. Granular compositions are usually in the 
following range: 
______________________________________ 
% by weight 
Pyridyltriazinone 1 - 10 
compound (I) 
Surfactant 0 - 2 
Inert carrier 99 - 88 
______________________________________ 
Somewhat less economically, the pyridyltriazinone compounds (I) may be 
dispersed in a dough composed of damp clay or any other inert carrier, and 
the resulting dispersion is then dried and coarsely ground to produce the 
desired granular product. 
The best application rate of the pyridyltriazinone compounds (I) for the 
control of a given weed varies, of course, depending upon the method of 
compound application, climate, soil type, water and organic matter 
contents of the soil and other factors known to those skilled in plant 
science. It will be found, however, that the optimum application rate is 
in the range of from 0.25 to 300 g/are in virtually every case. The 
optimum rates will usually be found to be within the preferred range of 
from 0.25 to 100 g/are. 
The time when the pyridyltriazinone compounds (I) should be applied to the 
soil or the weeds is widely variable, since they are effective both 
pre-emergence and post-emergence. At least some control of weeds will 
result from application of the compounds at any time when weeds are 
growing or germinating. They may also be applied to the soil during a 
dormant season to kill weeds germinating during the following warm season. 
When the pyridyltriazinone compounds (I) are used for weed control in an 
annual crop, it is usually best to apply a pre-emergence application of 
the compound to the soil at the time the crop is being planted. If the 
compound is to be soil incorporated, it will usually be applied and 
incorporated immediately before planting. If it is to be surface applied, 
it is usually simplest to apply the compound immediately after planting.

The following shows some specific examples of the composition suitable for 
herbicidal use, in which part(s) and % are by weight, and the numbers of 
the compounds used as the active ingredient correspond to those in Table 
1: 
EXAMPLE A 
Wettable Powder 
Twenty-five parts of Compound No. 1, 5 parts of a surfactant (i.e. 
polyoxyethylene alkylaryl ether) and 70 parts of talc are pulverized and 
mixed well to make a wettable powder preparation containing the active 
ingredient in 25 % concentration. 
EXAMPLE B 
Emulsifiable Concentrate 
Thirty parts of Compound No. 4, 20 parts of a surfactant (i.e. polyethylene 
glycol ether) and 50 parts of cyclohexanone are mixed well to make an 
emulsifiable concentrate preparation containing the active ingredient in 
30 % concentration. 
EXAMPLE C 
Granules 
Five parts of Compound No. 1, 40 parts of bentonite, 50 parts of clay and 5 
parts of sodium lignosulfonate are pulverized and mixed well. The 
resulting mixture is well kneaded with water, granulated and dried to 
obtain a granular preparation containing the active ingredient in 5 % 
concentration. 
EXAMPLE D 
Granules 
Three parts of Compound No. 3 and 97 parts of clay are pulverized and mixed 
well to make a granular preparation containing the active ingredient in 3 
% concentration. 
EXAMPLE E 
Fine Granules 
Five parts of Compound No. 2, 4 parts of sodium lignosulfonate, 86 parts of 
clay ("Fubasami clay", trademark of Fubasami Clay Co., Ltd.) and 5 parts 
of weight of water are kneaded by means of a ribbon mixer and dried to 
obtain a fine granular preparation containing the active ingredient in 5 % 
concentration. 
The pyridyltriazinone compounds (I) can control plant diseases and are 
particularly effective in controlling or exterminating plant diseases such 
as stem rot of vegetables (Sclerotinia spp.) and gray mold of vegetables 
(Botrytis spp.). Furthermore, they have a strong protective activity 
against plant pathogens such as rice blast (Pyricularia oryzae), sheath 
blight of rice (Pellicularia sasakii), helminthosporium leaf spot of rice 
(Cochliobolus miyabeanus), bacterial leaf blight of rice (Xanthomonas 
oryzae), brown rot of peach (Sclerotinia cinerea), blossom blight of apple 
(Sclerotinia mali), damping off yellows of the Japanese radish (Fusarium 
oxysporum f. raphani), southern blight of kidney bean (Corticium rolfsii), 
powdery mildew of cucumber (Sphaerotheca fuliginea), anthracnose of 
cucumber (Colletotrichum spp.), late blight of tomato (Phytophthora 
infestans), black spot of pear (Alternaria kikuchiana), alternaria leaf 
spot of apple (Alternaria mali), ripe rot of grape (Glomerella cingulata), 
early blight of tomato (Alternaria solani) and bacterial canker of citrus 
(Xanthomonus citri). Accordingly, they are useful as fungicides in 
agriculture. 
The pyridyltriazinone compounds (I) also exhibit a strong antimicrobial 
activity on other microorganisms than the plant pathogens as described 
above. Thus, they can be used in combination with various industrial 
articles or products such as synthetic resins, paints, paper and fiber 
products for protection from bacterial or fungal infestation or damage. 
Further, they can be used as antimicrobial additives, washing agents, 
antiseptic agents and the like. Moreover, they can control or exterminate 
slimes, algae and other injurious organisms which attach to various bodies 
in the sea and do damage thereto, so that they may be applied, in various 
preparation forms, to water for industry, cooling and paper-making thus 
controlling the slimes, algae and the like which generate in the water. 
Advantageously, the pyridyltriazinone compounds (I) are very low in 
toxicity to mammals and fishes and hardly irritate the skin even at the 
actual concentration in use. Thus, they have a very high safety and 
practicality. 
For exterminating algae and microorganisms or for controlling injurious 
life in water, they may be used in any of the common preparation forms 
such as dusts, wettable powders, oil sprays, aerosols, tablets, 
emulsifiable concentrates, granules, fine granules and fumigants. In 
general, the preferred content of the active ingredient(s) (optionally 
including other active components) in the preparation is from 0.1 to 95.0 
% by weight, preferably from 0.2 to 90.0 % by weight, and the preferred 
amount of the active ingredient(s) used is usually from 1 to 3,000 g/10 
are, preferably from 10 to 2,000 g/10 are. In the field application, the 
active ingredient(s) are generally used in a concentration of 1.0 to 0.01 
% by weight according to the object of application. The amount and 
concentration used depend upon the preparation forms, application time, 
application methods, places and objects for application and the like so 
that they may be changed freely irrespective of the ranges described 
above. The above-mentioned preparations can be used effectively by any of 
the application methods, for example, dusting (scattering of dusts), 
spraying, scattering of granules, soil-treatments, dressing, coating, 
dipping and the like. 
The pyridyltriazinone compounds (I) can also be applied by the ultra-low 
volume spraying method, for example, in such a high concentration as 95 % 
by weight of the active ingredient or as 100 % by weight of the active 
ingredient. In the case of granules, the particle size is made uniform in 
the vicinity of 250 mesh, and they are applied according to the object of 
application. 
Furthermore, the pyridyltriazinone compounds (I) can be applied in 
combination with other chemicals such as Blasticidin-S, Kasugamycin, 
Polyoxin, Validamycin, Cellocidin, 
3-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl] glutarimide, 
streptomycin, griseofluvin, pentachloronitrobenzene, pentachlorophenol, 
hexachlorobenzene, trichloronitromethane, 1,1,1-trichloro-2-nitroethane, 
dichlorodinitromethane, trichloronitroethylene, 
1,1,2,2,-tetrachloronitroethane, methylene-bis-thiocyanate, 
2,6-dichloro-4-nitroaniline, zinc ethylene-bis-dithiocarbamate, zinc 
dimethyldithiocarbamate, manganous ethylene-bis-dithiocarbamate, 
bis(dimethylthiocarbamoyl)disulfide, 2,4,5,6-tetrachloroisophthalonitrile, 
2,3-dichloro-1,4-naphthoquinone, tetrachloro-p-benzoquinone, 
p-dimethylaminobenzene diazo sodium sulfonate, 
2-(1-methylheptyl)-4,6-dinitrophenyl crotonate, 2-heptadecylimidazoline 
acetate, 2,4-dichloro-6-(o-chloroanilino)-S-triazine, dodecylguanidine 
acetate, 6-methyl-2,3-quinoxalinedithiol cyclic-S,S-dithiocarbonate, 
2,3-quinoxalinedithiol cyclic trithiocarbonate, 
N-trichloromethylthio-4-cyclohexene-1,2-dicarboxyimide, 
N-(1,1,2,2-tetrachloroethylthio)-4-cyclohexene-1,2-dicarboxyimide, 
N-(dichlorofluoromethylthio)-N-(dimethylsulfamoyl)-aniline, 
1,2-bis-(3-methoxycarbonyl-2-thioureido)benzene, 
1,2-bis-(3-ethoxycarbonyl-2-thioureido)benzene, 2-amino-1,3,4-thiadiazole, 
2-amino-5-mercapto-1,3,4-thiadiazole, O-phenylphenol, 
N-(3,5-dichlorophenyl)maleimide, N-(3,5-dichlorophenyl)succinimide, N-(3,5 
-dichlorophenyl)itaconimide, 
3-(3,5-dichlorophenyl)-5,5-dimethyloxazolidine-2,4-dione, 2,3-dihydro-5 
-carboxanilide-6 -methyl-1,4-oxathiine-4,4-dioxide, 
2,3-dihydro-5-carboxanilide-6methyl-1,4-oxathiine, 1-(N-n-butylcarbamoyl)- 
2-methoxycarbonylaminobenzimidazole, 
O,O-diisopropyl-S-benzyl-phosphorothioate, 
O-ethyl-S,S-diphenylphosphorodithioate, 
O-butyl-S-benzyl-S-ethylphosphorodithioate, O-ethyl-O-phenyl-O-( 
2,4,5-trichlorophenyl)phosphate, O,O-dimethyl-O-( 
3-methyl-4-nitrophenyl)phosphorothioate, S-[1,2-bis-(ethoxycarbonyl)ethyl] 
-O,O-dimethylphosphorodithioate, 
O,O-dimethyl-S-(N-methylcarbamoylmethyl)phosphorodithioate, 
O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidyl)thiophosphate, 
3,4-dimethylphenyl-N-methylcarbamate, iron methanearsonate, ammonium iron 
methanearsonate, 2-chloro-4,6-bis-(ethylamino)-S-triazine, 
2,4-dichlorophenoxyacetic acid (including salts and esters thereof), 
2-methyl-4-chlorophenoxyacetic acid (including salts and esters thereof), 
2,4-dichlorophenyl-4'-nitrophenyl ether, sodium pentachlorophenolate, 
N-(3,4-dichlorophenyl)-propionamide, 3-(3,4-dichlorophenyl)- 1,1 
-dimethylurea, .alpha.,.alpha. ,.alpha. 
2,6-dinitro-N,N-di-n-propyl-p-toluidine, 
2-chloro-2',6'-diethyl-N-(methoxymethyl)acetamide, 
1-naphthyl-N-methylcarbamate, methyl-N-(3,4-dichlorophenyl)carbamate, 
4-chlorobenzyl-N,N-dimethylthiolcarbamate, N,N-diallyl-2-chloroacetamide, 
O-ethyl-O-(3-methyl-6-nitrophenyl)-N-sec.-butylphosphorothioamidate, 
S-n-butyl-S'-(p-tert.-butylbenzyl)-N-(3-pyridyl)imidodithiocarbonate and 
S-n-heptyl-S'-(p-tert-butylbenzyl)-N-(3-pyridyl)imidodithiocarbonate. 
In these cases, the individual active ingredient in the mixed prepration 
does not show a reduction in its own controlling effect, so that it is 
possible to control two or more kinds of injurious organisms at the same 
time. Further, a synergistic effect due to mixing which is expected to be 
sufficiently effective is observed with some combinations. 
The pyridyltriazinone compounds (I) can also be used in combination with 
other agricultural chemicals such as fungicides, nematocides and 
acaricides and/or fertilizers. 
For an industrial use, the pyridyltriazinone compounds (I) can be applied 
in the pure form without adding other inert components. They are soluble 
in most solvents so that the compounds may be formulated into a suitable 
preparation form such as a solution, together with other inert components 
(various carriers), and applied by mixing with industrial products or by 
coating, injection, dipping or the like as the need arises. 
When the pyridyltriazinone compounds (I) are used for industrial purposes, 
they can directly be incorporated in the materials to be protected, for 
example, fiber products (particularly blended materials of cellulose or 
viscose), materials containing synthetic resin substrates such as 
polyamide or polyvinylchloride, casein-containing paints or lacquers, 
inorganic or organic pigments, thickening agents made from starch or 
cellulose derivatives, animal viscous materials or oils, permanent 
dressings containing polyvinyl alcohol as a substrate, cosmetics such as a 
soap or cream, ointments, powders, tooth-powders and the like. Further, 
the compounds of this invention can be used in the form of an aerosol, dry 
cleaner, organic solution for use as a impregnant for wood, and emulsified 
solution. 
Still further, the pyridyltriazinone compounds (I) can be used for 
protecting substances which are easy to rot, for example, leather, paper 
and the like in the form of an aqueous suspension together with a wetting 
agent or dispersing agent. 
The preferred application of the pyridyltriazinone compounds (I) is 
disinfection of washed products and protection of the products from attack 
of microorganisms. For this purpose, it is preferred to use the 
pyridyltriazinone compounds (I) in the form of a washing liquor containing 
them in 0.1 to 500 ppm concentration. But the concentration is not always 
limited to this range. 
The pyridyltriazinone compounds (I) are soluble in most organic solvents, 
irrespective of a hydrophilic solvent or a solvent which is immiscible 
with water, for example, benzene, xylene, ether, dioxane, acetone, methyl 
isobutyl ketone, cyclohexanone, isophorone, chloroform, trichloroethane, 
methylcellosolve, ethylcellosolve, butylcellosolve, dimethylformamide, 
dimethylsulfoxide, acetonitrile, methylnaphthalene and the like. 
The pyridyltriazinone compounds (I) of this invention may be used, rather 
preferably, in combination with the following fungicides which have 
conventionally been used for industrial purposes, and in this case the 
controlling effect of the component active ingredients does not reduce due 
to the combination but rather a synergistic effect due to the combination 
is sufficiently expected: halogenated phenols such as pentachlorophenol, 
2,4,5-trichlorophenol, 2,4,6-trichlorophenol and salts thereof, copper 
compounds such as cuprous oxide, cupric oxide and copper naphthenate, tin 
compounds such as bis(tributyltin)oxide, bis(tributyltin)chloride, 
bis(tributyltin)acetate and bis(tributyltin)hydroxide (in this case, the 
tributyl group may be replaced by a trialkyl or triphenyl group), 
aminobenzoic esters such as butyl p-aminobenzoate, salicylic acid 
derivatives such as salicylanilide and halogenated salicylanilide, 
chlorhexidine, monoalkyl-bis(aminoethyl)glycine and salts thereof, 
1,2-benzisothiazolin-3-one, benzyl bromoacetate, 
2-(4-thiazolyl)benzimidazole, p-chloro-m-xylenol, 
2,2'-dihydroxy-5,5'-dichlorophenylmethane, dehydroacetic acid, formalin, 
nitrofurans, oxyquinolines, o-phenylphenol, biphenyl, cresol soap, 
creosote, dimethyl zinc, dithiocarbamates, benzothiazoles, 
methylene-bis-thiocyanate, etc. 
The following description shows some specific examples of the composition 
suitable for fungicidal use, in which part(s) and % are by weight, and the 
numbers of the compounds used as the active ingredient correspond to those 
in Table 1: 
EXAMPLE O 
Wettable Powder 
Fifty parts of Compound No. 1, 5 parts of a wetting agent (i.e. 
alkylbenzenesulfonate) and 45 parts of diatomaceous earth are pulverized 
and mixed well to make a wettable powder preparation containing the active 
ingredient in 50 % concentration. 
EXAMPLE P 
Dust 
Seven parts of Compound No. 2 and 93 parts of clay are pulverized and mixed 
well to make a dust preparation containing the active ingredient in 7 % 
concentration. 
EXAMPLE Q 
Pellets 
Eight parts of Compound No. 3, 35 parts of bentonite, 52 parts of clay and 
5 parts of sodium ligninsulfonate are pulverized and mixed well. The 
mixture is kneaded with water and pelletized to make a pellet preparation 
containing the active ingredient in 8 % concentration. 
EXAMPLE R 
Emulsifiable Concentrate 
Twenty parts of Compound No. 4, 15 parts of an emulsifier (i.e. 
polyoxyethyleneglycol ether) and 65 parts of cyclohexanol are mixed well 
to make an emulsifiable concentrate preparation containing the active 
ingredient in 20 % concentration. 
EXAMPLE S 
Granules 
Five parts of Compound No. 4, 93.5 parts of clay and a binder (i.e. 
polyvinyl alcohol) are sufficiently pulverized and mixed together. The 
resulting mixture is kneaded with water, granulated and dried to obtain a 
granular preparation containing the active ingredient in 5 % 
concentration. 
Some of the test results which support the herbicidal and fungicidal 
effects of the pyridyltriazinone compounds (I) are shown in the following 
Examples wherein part(s) are by weight. In these Examples the numbers of 
the compounds according to this invention correspond to those as shown in 
Table 1, while the numbers of the known compounds for comparison 
correspond to those as shown in the following table: 
Table 2 
______________________________________ 
Com- 
pound 
No. Chemical structure Literature 
______________________________________ 
##STR9## Japanese Pat. Pub. No. 20106/1970 
ii 
##STR10## Japanese Pat. Pub. No. 20106/1970 
iii 
##STR11## Japanese Pat. Pub. No. 20106/1970 
iv 
##STR12## Japanese Pat. Pub. No. 315/1969 
v 
##STR13## Japanese Pat. Pub. No. 20106/1970 
vi 
##STR14## Japanese Pat. Pub. No. 20106/1970 
______________________________________ 
EXAMPLE I 
Pre-emergence Application 
Taking large crabgrass (Digitaria sanguinalis) as a representative of 
grassy weeds, redroot pigweed (Amaranthus retroflexus) and common 
lambsquarter (Chenopodium album) as representatives of broad-leaved weeds 
and wheat and radish as representatives of crops, seeds of the grasses and 
crops were each sowed in 10 cm flower pot and covered with soil. Each 
emulsifiable concentrate containing the test compound was diluted with 
water and applied to the soil treatment by means of a hand sprayer. Each 
of the grasses and crops was grown up in a green-house, and the herbicidal 
activity of the test compound was checked 20 days after the application. 
The herbicidal activity was evaluated by the following numerals ranging 
from 0 to 5 as follows: 
______________________________________ 
Numeral Percentage of inhibition (%) 
______________________________________ 
0 0 
1 20 
2 40 
3 60 
4 80 
5 100 
______________________________________ 
The results are shown in Table 3. 
Table 3 
______________________________________ 
Amount Large 
Compound 
applied crab- Redroot 
No. (g/a) grass Radish pigweed Wheat 
______________________________________ 
1 20 5 0 5 0 
10 5 0 5 0 
2 20 5 2 5 0 
10 5 0 5 0 
3 20 5 1 5 0 
10 5 0 5 0 
4 100 5 0 5 0 
50 5 0 5 0 
i 20 4 4 4 4 
10 3 4 2 4 
v 20 4 4 4 1 
10 3 3 2 0 
vi 20 4 4 3 4 
10 2 4 2 3 
______________________________________ 
EXAMPLE II 
Flood-water Application 
A Wagner pot of 14 cm in diameter was filled with 1.5 kg of paddy field 
soil and brought into the state of a paddy field. In the pot were 
transplanted rice seedlings of a 3-leaf stage and further were sowed seeds 
of barnyard grass (Echinochloa crus-galli). A required amount of the test 
compound was applied to the soil under a water-logged condition. 
Twenty-five days after the application, the herbicidal activity and 
phytotoxicity of the test compound were checked on the transplanted and 
sowed plants and spontaneously germinated broadleaved weeds such as 
monochoria (Monochoria viaginalis Presl.), false pimpernel (Linderna 
pyxidaria) and toothcup (Rotala indica Koehne). 
As for the application, a wettable powder containing a pre-determined 
amount of the test compound was applied in a proportion of 15 ml/pot by 
means of a pipette. The herbicidal activity was evaluated by the following 
numerals ranging from 0 to 5. 
______________________________________ 
Numerals Percentage of inhibition (%) 
______________________________________ 
0 0 
1 20 
2 40 
3 60 
4 80 
5 100 
______________________________________ 
As for the evaluation of phytotoxicity, the three factors (i.e. height of 
grass, number of tillers and total weight (dry weight)) were each checked, 
and a ratio of the treated plot to the untreated plot was calculated for 
each factor. The phytotoxicity was evaluated based on the lowest value of 
the three ratios which was classified into the following grades ranging 
from 0 to 5. 
______________________________________ 
Grade Ratio of the untreated plot (%) 
______________________________________ 
0 100 
1 80 
2 60 
3 40 
4 20 
5 0 
______________________________________ 
The results are shown in Table 4. 
Table 4 
______________________________________ 
Amount Herbicidal activity 
Compound 
applied Barnyard Broad- Phyto-toxicity 
No. (g/a) grass grass (Wheat) 
______________________________________ 
1 20 5 5 1 
10 5 5 0 
2 20 5 5 1 
10 5 5 0 
3 20 5 5 0 
10 5 3 0 
4 100 4 5 0 
50 4 4 0 
i 20 3 2 2 
10 2 1 1 
v 20 3 3 3 
10 1 2 2 
vi 20 3 3 2 
10 3 2 1 
______________________________________ 
EXAMPLE III 
Protective activity on rice blast (Pyricularia oryzae) 
Rice plants (var.: Wase-Asahi) were grown up to a 3-leaf stage in a 10 cm 
flower pot. Each solution containing a pre-determined amount of the test 
compound was sprayed on the rice plants in a proportion of 7 ml/pot. After 
one day, a spore suspension of Pyricularia orysae was inoculated by 
spraying, and the fungicidal activity of the test compound was checked. 
The percentage of control was calculated from the following equation: 
##EQU1## 
The results are shown in Table 5. 
Table 5 
______________________________________ 
Concentration of 
Compound active ingredi- 
Percentage of 
Phyto- 
No. ent (ppm) control toxicity 
______________________________________ 
1 100 100.0 None 
2 100 100.0 " 
3 100 100.0 " 
4 100 93.7 " 
i 100 5.4 " 
Untreated 
-- 0 -- 
plot 
______________________________________ 
EXAMPLE IV 
Use in Washing Liquor 
One part of the test compound (i.e. Compound No. 1 or 2) was dissolved in 
20 parts of dimethylsulfoxide, and the resulting solution was added to a 
washing liquor containing sodium soap of 1.5 g per liter so as to make a 
concentration of 25 mg of the test compound per liter. White cotton fabric 
(1 part) was dipped in the resulting liquor (20 parts), and the bath was 
heated at 80.degree. C. The fabric material was treated at the same 
temperature for 20 minutes and rinsed at first for 40 minutes and next for 
3 minutes with soft water. Thereafter the fabric material was dehydrated 
by a centrifuge, dried and ironed. The finished fabric material was cut 
into round test pieces of 20 mm in diameter. The test pieces were placed 
on the agar medium in a Petri dish inoculated with either Staphylococcus 
aureus 209P or Escherichia coli K-12 and incubated for 24 hours, and 
incubation was carried out at 37.degree. C. for 24 hours. After the 
incubation, it was found that the microorganisms did not live on the test 
pieces treated with each of Compound Nos. 1 and 2 and that the area where 
the microorganisms did not exist was formed at the outer part of the test 
pieces placed on the agar. 
EXAMPLE V 
Preservation of Fresh Fish from Decay 
A 1 % aqueous solution of the test compound was prepared and added to sea 
water so as to make a predetermined concentration of the test compound. 
Horse mackerels were dipped in the sea water for about 30 minutes, 
dehydrated and preserved at 5.degree. C. in a refrigerator. A degree of 
freshness was decided by determining the amount of the volatile basic 
nitrogen contained in the fish according to the Kjeldahl's method. 
The results are shown in Table 6. 
Table 6 
______________________________________ 
Concentra- 
tion of 
active in- 
Amount of volatile basic 
gredient nitrogen (mg %) 
Compound in sea water 
After After After 
No. (ppm) 3 days 8 days 12 days 
______________________________________ 
1 5 10 18 28 
2 5 10 21 31 
4 5 10 19 30 
i 5 15 36 71 
iii 5 16 39 73 
Un- 
treated 0 18 46 80 
plot 
______________________________________ 
EXAMPLE VI 
Use in Synthetic Resin 
Sixty-five parts of polyvinyl chloride powder, 35 parts of dibutyl 
sebacate, 2 parts of dibutyltin dilaurate and 0.5 part of the test 
compound (i.e. Compound No. 1 or 2) were mixed. The mixture was uniformly 
kneaded at 160.degree. C. for 10 minutes on a set of mixing roller and 
extruded into a sheet of 0.3 mm in thickness. The sheet was cut into round 
test pieces of 20 mm in diameter, and the test pieces were treated in the 
same manner as in Example IV. Neither Staphylococcus aureus 209 P nor 
Escherichia coli K-12 was detected on the test pieces treated with each of 
Compounds Nos. 1 and 2, and that the area where the microorganisms did not 
exist was formed at the outer part of the test pieces placed on the agar. 
EXAMPLE VII 
Protective Activity on White Water 
Ten grams of each of the test compounds (i.e. Compound Nos. 1, 2, 3 and 4) 
were dissolved or suspended in 100 ml of water, and 5 ml of each solution 
was diluted with 1 liter of the white water resulting from a 
groundwood-pulp production process. Five milliliters of each resulting 
solution was further diluted with 2 liters of the white water. To 100 ml 
of the test solution thus obtained were added 10 g of grape sugar, 1 g of 
peptone, 0.05 g of magnesium sulfate and 0.01 g of calcium chloride, and 
the mixture was sterilized by heating and inoculated with Bacillus sp. 
isolated from the slime resulting from a paper-making process. Propagation 
of the fungus was not detected at all. 
EXAMPLE VIII 
Use in Paint 
______________________________________ 
Materials Parts 
______________________________________ 
Test compound 10 
Zinc oxide 20 
Red iron oxide 10 
Precipitated barium 10 
sulfate 
Linseed oil 10 
Rosin 20 
Naphtha 20 
______________________________________ 
Three grams of the paint prepared by the above-mentioned formulation was 
applied by brushing on a vinyl-chloride resin panel (30 cm.times. 20 
cm.times. 5 mm) and dried. Each panel was attached to a wooden frame and 
dipped in the sea (the Toba Bay, Mie Prefecture, Japan) so that the lower 
half of the panel was under the sea surface (June 20th). After two months, 
the panel was taken out and the protective activity was checked and 
evaluated based on the proportion of the area to which marine life 
attached. The criteria for evaluation were as follows: 
______________________________________ 
Evaluation Index 
Proporation of the area 
______________________________________ 
0 No life attached 
1 Less than 2 % 
2 2 - 5 % 
3 5 - 20 % 
4 20 - 60 % 
5 More than 60 % 
______________________________________ 
The results are shown in Table 7. 
Table 7 
______________________________________ 
Compound Marine life 
No. Slime Sea lettuce Barnacle 
______________________________________ 
1 0 0 0 
2 0 1 1 
3 0 1 1 
4 1 1 2 
i 3 4 4 
ii 4 4 5 
iii 3 4 4 
iv 4 4 5 
Untreated 5 5 5 
plot 
______________________________________