JPH0717625B2 - Thiadiadinone derivative and herbicide - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides tetrahydro-1,3, represented by the following general formula:
The present invention relates to a 5-thiadiazin-4-one derivative and a herbicide containing the compound as an active ingredient.

(However, R _{1 is} alkyl, substituted phenyl, or benzoyl; R _{2 is} alkyl or aryl; R _{3 is} nitrile, alkoxycarbonyl, or alkylyl.) Tetrahydro-1,3 represented by the above general formula of the present invention. ,
The 5-thiadiazin-4-one derivative is a novel compound which has not been published in the literature, patents or the like, and as a result of various studies conducted by synthesizing the 5-thiadiazin-4-one derivative, it was found to have an excellent action as a herbicide.

That is, the compound of the present invention shows a strong herbicidal activity against a wide range of weeds, and the active ingredient is added in an amount of 2 to 20 per hectare immediately before germination of the weeds or at the early stage of its growth.
When applied in kg, a wide range of weeds as described below can be killed.

In addition, by limiting the dose of the compound or applying an appropriate application method, specific crops such as corn, potato, sugar cane, peanut, soybean, sunflower, barley, wheat, sorghum, paddy rice, cotton and fruit trees can be obtained. Weeds can be selectively controlled in the field where they are cultivated.

Typical examples of the compound of the present invention include those shown in Table 1.

The compounds are represented by the symbols in the above general formula. In the physical property column, NMR is a nuclear magnetic resonance spectrum, () is a solvent, mp is a melting point, and η _D is a refractive index. The notation was according to a conventional method.

The compound is, for example, a compound (A) obtained by reacting a compound containing active methylene with isothiocyanate under a suitable base and N-chloromethyl-N-substituted carbamoyl chloride synthesized by a known method. A suitable base,
For example, in the presence of potassium carbonate, potassium hydroxide, etc., in an appropriate inert solvent such as acetone, dioxane, etc.
It is obtained by reacting at a temperature of ℃ to 60 ℃ for 1 to 20 hours.

Hereinafter, typical synthetic examples of the compound of the present invention will be shown, and the compounds will be described more specifically.

Synthesis Example 2-Dicyanomethylene-5-methyl-3-phenyl-tetrahydro-1,3,5-thiadiazin-4-one Phenyl isothiocyanate 6.8 g (0.05 mol) and alon nitrile 3.3 g (0.05 mol) in a small amount of ethanol. After stirring, add sodium ethylate (containing 1.2 g of Na) dropwise with stirring and stir for 30 minutes. Further, 7.1 g (0.05 mol) of N-chloromethyl-N-methylcarbamoyl chloride was added dropwise, and the mixture was stirred at room temperature for 30 minutes, stirred at 40 ° C for 2 hours, reacted with sodium hydrogen carbonate solution, extracted with benzene, washed with water, dehydrated and concentrated. Then oil is obtained. Purification with a silica gel column gives 1.8 g of white crystals.

The active compound according to the present invention can be made into a dosage form such as an emulsion, a wettable powder, a paste, a flowable powder, a granule and the like by applying a usual formulation means.

Furthermore, the compound of the present invention can be mixed with other herbicides. Further, in order to expand the range of action, it can be mixed with a pesticide other than a herbicide, for example, an insecticide or a fungicide.

Next, examples of typical dosage forms will be given. "Part" in the description
Indicates parts by weight.

Example 1. Wettable powder 50 parts of the compound shown in Table 1 as an active ingredient, 10 parts of diatomaceous earth, 35 parts of clay, 3 parts of sodium polyoxyethylene alkylallyl ether sulfonate and 2 parts of sodium alkylnaphthalene sulfonate are used. A wettable powder containing 50% of the active ingredient compound is obtained by mixing and grinding.

Before use, dilute with water to the specified concentration and spray.

Example 2. Granules 5 parts of the compound of Table 1, 20 parts of bentonite, 73 parts of clay and 2 parts of sodium dodecylbenzene sulfonate were mixed, and water was added.
After adding 20 parts and kneading with a kneading machine, the resulting mixture is granulated through a granulator and then dried and sized to obtain a granule containing 5% of the active ingredient.

Example 3 Emulsion 15 parts of the compound shown in Table 1 as an active ingredient, 80 parts of xylene and 5 parts of polyoxyethylene alkylallyl ether were mixed into a uniform solution to obtain an emulsion containing 15% of the active ingredient. . Before use, dilute with water to the specified concentration and spray.

Novel tetrahydro-1,3,5-thiadiazines of general formula I
Since the 4-one derivative has an excellent herbicidal action, it is suitable for controlling weeds growing in fields, paddy fields, orchards, non-agricultural land and the like. When this active compound is sprayed on the surface of the soil or mixed in the soil, the growth of weeds can be significantly inhibited and the weeds can be killed. It is also possible to control the weeds by spraying this agent on the foliage of growing weeds.

The dose of this compound is regulated and the application rate is 2 per hectare.
When selected to -20 kg, it can be used as a selective herbicide in a cultivation field such as paddy rice, corn, wheat, barley, sugar cane, soybean, peanut, sunflower, potato, cotton or fruit tree. Further, if the application rate is increased, it can be applied as a non-selective herbicide.

The compounds of the present invention can be used for controlling the following weeds, for example. That is, dicotyledonous plants, such as chickweed (Stellaria media), white clover (Chenopodium), clover (Sagima japonica), and cocca (Chonopodium f).
icifolium), giant cattle (Polygonum nodosum), purslane (Portulace oleracea), tuna (capsella b)
ursapastoris), Gumbai Nazuna (Lepidium virginicu)
m), Pepper (Porippa indica), Rana esculenta (C)
ardamine Hexuosa), Abutilon avicennae,
American stag deer (Sida spinosa), Malaba morning glory (Ipomoea purpurea), scrotum (Senecio vulgari)
s), Onnogeshi (Sonchus asper), American Sendangusa (Bidens frondosa), Ragweed (Ambrosia artemi)
siaefolia), broom (Aster subulatus), hen (Lamium am plexicavle), oxalis (Oxalis cor)
nicolate), amaranthus (Amaranthus retroflexus), red pea (Vicia sativa), yamgra (Galium)
spurium), Puffin (Solanum nigrum), morning glory (Datura stramonium), eel (Monocho)
ria vaginalis) and other grasses such as Poa annua and Alopeculus ae.
qualis), crabgrass (Digitaria adsendens), crabgrass (Eleusine indica), green locust (Setaria virid)
is), barnyard grass (Echinochlor crus-galli), duckweed (Agropyron tsukushiensis), barley (Lolium pe)
renne), rye (Bromus catharticos), oats (Avena tatua), and frog (Polypogon Higegawer)
i), millet (Panicum dichotom-iflorom), Cyperus weeds, for example Cyperus micr
oiria), Kogomegayatsuri (Cyperus lria), pine (Eleocharis acicularia), etc.

The compound of the present invention has excellent herbicidal activity against a wide range of weeds as described above, and in particular, the weeds are sprayed on the field surface or the foliage surface of the plant or in the submerged water immediately before the germination or immediately after the germination. When this is done, an extremely high control effect is obtained.

Further, when the compound of the present invention is mixed in the soil, an extremely excellent herbicidal control effect can be obtained.

In order to show the herbicidal effect of the herbicide according to the present invention, some typical test examples will be described in more detail.

Test Example 1 Herbicidal effect on plants when per-emergence soil treatment was performed. A pot of 100 cm ² was filled with volcanic ash soil, and
gitaria sanguinalis), Northern millet (Echinochloa crus-
galli), Polygonum nodosum, Amaranthus retroflexus, Corn (Zea ma
ys), wheat (Triticum aestivum), mung bean (Phase)
olus radiatus) seeds, covered with about 5 mm of soil, and immediately after that, a compound as listed in Table 1 is prepared as a wettable powder according to Example 1, diluted with water, A dose corresponding to 10 kg of components per hectare was applied to the soil surface of each pot. The herbicidal effect on the plants was investigated 2 weeks after the treatment. The herbicidal effect was visually observed and displayed in Table 2 by 6-level indexes of 0: no effect to 5: complete death.

Test Example 2 Herbicidal effect on plants when subjected to Foliar spray treatment A pot with a surface area of 100 cm ² was filled with volcanic ash soil, and a Japanese cedar (Digitaria sanguinalis) and a barnyard grass (Echinochloa c)
rus-galli), Polygonum nodosum, Amaranthus retroflexus, Corn (Ze)
a mays), wheat (Triticum aestivum), mung bean (P
haseolus radiatus) seeds, covered with about 1 cm of soil and placed in a greenhouse, and when weeds have 1 to 2 leaves, a wettable powder of the compound of the present invention is applied at a dose equivalent to 10 kg per hectare.
It was diluted with water equivalent to 1000 l / ha and sprayed using a sprayer. Ten days after the chemicals were sprayed, the same criteria as in Test Example 1 were investigated, and the results were displayed as a 6-level index. The test results are shown in Table 3.

Test Example 3 Herbicidal effect on paddy field weeds and phytotoxicity test on paddy rice A pot with a surface area of 120 cm ² was filled with paddy field soil, and the novier (Echino
choa crus-galli), eel (Mono-choria vaginalis)
Seeds of pineapple (Eleocha)
ris acicularis) and 2-leaf stage rice weeds are transplanted to 2 places each, and the water depth is maintained at about 3 cm. After 3 days, the compound of the present invention was administered in water with a wettable powder prepared according to Example 1 in an amount corresponding to 10 kg per hectare. The herbicidal effect and the phytotoxicity to paddy rice were investigated 3 weeks after the chemical treatment. The herbicidal effect and the phytotoxicity to crops were investigated by the same criteria as in Test Example 1 and expressed by 6-level index. The test results are shown in Table 4.

From Table 4, it can be seen that the compounds of the present invention are effective in killing the important weeds of paddy fields, such as Nobie, Konagi and Matsuba.

Claims (2)

[Claims] 1. A general formula (Provided that R _{1 is} alkyl, substituted phenyl, or benzoyl; R _{2 is} alkyl or aryl; R _{3 is} nitrile, alkoxycarbonyl, or alkylyl, respectively.), And tetrahydro-1,3,5-thiadiazine-4. -One derivatives. 2. General formula (Provided that R _{1 is} alkyl, substituted phenyl, or benzoyl; R _{2 is} alkyl or aryl; R _{3 is} nitrile, alkoxycarbonyl, or alkylyl, respectively.), And tetrahydro-1,3,5-thiadiazine-4. -A herbicide containing an on derivative as an active ingredient.