JPH01128987A - Thiadiazoloazine compound and herbicide containing the same - Google Patents

Abstract

NEW MATERIAL:A compound of formula I {J is formula II-V [X is H, halogen, alkyl which may be halogenated, alkoxy which may be halogenated; Y is H, halogen, alkyl which may be halogenated]; R1, R2 are alkyl, alkoxy, Cl; Z is -CH=, =N-; where R1 and R2d are not Cl simultaneously}. EXAMPLE:5,7-Dimethoxy-2-(3-dimethylaminocarbonyl-2-thiophenesulfonyl) imino-281,2,4-thiadiazolo[2,3-a]pyrimidine. USE:Herbicide. PREPARATION:A thiourea compound of formula VI such as N-(3- dimethylaminocarbonyl-2-thiophenesulfonyl)-N'-(4,6-dimethoxy-2-pyridin yl)thiourea, is allowed to react with an oxidizing agent.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to novel thiadiazoloazine compounds, herbicides containing them as active ingredients, and methods for producing these compounds.

(Disclosure of the Invention) The compound of the present invention is a thiadiazoloazine compound represented by the following general formula (1).

General formula: elementary atom, halogen atom, alkyl group, haloalkyl group,
alkoxy group, haloalkoxy group, alkoxyalkyl group, haloalkoxyalkyl group) or -CO
Rs (Rs is a hydrogen atom, a cation or an alkyl group), Y is a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group, R and R2 are an alkyl group, an alkoxy group or a chlorine atom, Z -C11・
or *N-, except when RI and R1 are both chlorine atoms].

In the general formula (1), X, Y, R,, R2゜R3, R4
, and the alkyl moiety of the alkyl group or other substituents contained in R1 include those having 1 to 6 carbon atoms, such as methyl group, ethyl group, propyl group, butyl group, etc., and halogens related to X and Y As atoms, fluorine atoms,
Examples include chlorine atom, bromine atom, and iodine atom.

The novel compound of the present invention represented by the general formula (1) is:
For example, it can be manufactured by the following method.

[In the formula, J, R+, Rz and 2 are as described above] Examples of the oxidizing agent used in the above reaction include halogens such as chlorine and bromine; N-chlorosuccinimide, N-
N-halogenosuccinimides such as bromosuccinimide; N-halogenoacetamides such as N-chloroacetamide and N-bromoacetamide; Chloramine T;
Hypohalites such as sodium hypochlorite, potassium hypochlorite, calcium hypochlorite, and sodium hypobromite; alkylsulfonyl halides such as methanesulfonyl chloride and ethanesulfonyl chloride;
Hydrogen peroxide, performic acid; PerMs such as peracetic acid, perpropionic acid, perbenzoic acid; manganese dioxide, permanganate,
Metal-containing oxidizing agents such as dichromate; also sulfuric acid, nitric acid,
Air or the like can also be used.

Further, the above reaction is carried out in the presence of a solvent and an acid acceptor, if necessary.

Examples of solvents include water; alcohols such as methanol, ethanol, propatool, and butanol; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; chloroform, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, and n-hexane. , cyclic or acyclic aliphatic hydrocarbons such as cyclohexane; ethers such as diethyl ether, dioxane, and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile, and acrylonitrile; pyridine , triethylamine, N,N-dimethylaniline and other tertiary organic amines; dimethylformamide, N-
Examples include aprotic polar solvents such as methylpyrrolidone, dimethylsulfoxide, and sulfolane.

Examples of acid acceptors include inorganic bases such as sodium hydroxide, potassium hydroxide, alkali metal or alkaline earth metal carbonates, and organic bases such as triethylamine.

The thiourea compound which is an intermediate of the compound of the present invention represented by the general formula (n) can be produced, for example, by the following method.

(D) (wherein J, R+, Rz and Z are as described above, and 1
1al is a halogen atom, R6 is an alkyl group or an alkoxyalkyl group, R7 is a halogen atom, an alkyl group, or an alkoxy group, and examples of the halogen atom contained in R8R7 include a chlorine atom, a bromine atom, and an iodine atom. It will be done.

The above reaction is carried out in the presence of a solvent and an acid acceptor, if necessary.

As a solvent, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; cyclic or acyclic aliphatic hydrocarbons such as chloroform, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, n-hexane, and cyclohexane; diethyl Ethers such as ether, dioxane, and tetrahydrofuran; Ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone Nitriles such as acetonitrile, propionitrile, and acrylonitrile; Dimethyl formamide, N-
Examples include aprotic polar solvents such as methylpyrrolidone, dimethylsulfoxide, and sulfolane.

Examples of acid acceptors include inorganic bases such as sodium hydroxide, potassium hydroxide, alkali metal or alkaline earth metal carbonates, and organic bases such as triethylamine.

The compounds represented by the general formula (■) in the above reaction formulas (A) to (G) can be prepared according to the reaction formula (B), and the compounds represented by the general formulas (III) to (V) and (■) The compound is
For example, 8 rounds can be produced by the following methods tea) to (C).

cs,, KOH R6 \ (In the formula, J, R+, R,, R,, z and l1al are as described above) The above reaction can be performed according to the reaction formulas (A) to (G) as necessary.
It is carried out in the presence of a solvent and an acid acceptor that can be used in

Among the novel thiadiazoloazine compounds represented by the general formula (I), those in which J is a pyridyl group can also be produced by the following alternative method.

Rtl-Ls, aprotic polar solvent Rg-Hal,
An example of synthesis of a specific intermediate of the compound of the present invention will be described below.

Intermediate synthesis example 1. N-(3-dimethylaminocarbonyl-2-thiophenesulfonyl)-N'-(4,6-
Synthesis of 2-aminosulfonyl-N,N-dimethyl-3-thiophenecarboxamide, 0.35 g of 4,6-simethoxy2-isothiocyanatopyrimidine, 6.25 g of anhydrous potassium carbonate, and A mixture of 9 ml of acetone,
The reaction was completed by stirring at 40 to 45° C. for 14 hours under a nitrogen atmosphere.

After the reaction, the solid substance was filtered from the reaction mixture, suspended in 9 ml of water acidified with hydrochloric acid, filtered again, washed with water, and dried to obtain N-(3-dimethylaminocarbonyl- 2-thiophenesulfonyl') -N
0.60 g of '-(4,6-simethoxy2-pyrimidinyl)thiourea was obtained.

Intermediate synthesis example 2. Synthesis of N-(2-dimethylaminocarbonyl-3-pyridinesulfonyl)-N'-(4,6-simethoxy2-pyrimidinyl)thiourea.

0.15 g of 3-aminosulfonyl-N,N-dimethylpicolinamide, 0.13 g of 4,6-simethoxy 2-isothiocyanatopyrimidine, 90 m of anhydrous potassium carbonate
g, acetone 5m! ! The mixture was stirred at room temperature under nitrogen atmosphere for 20 hours to complete the reaction.

After the reaction, the solid substance was filtered from the reaction mixture, suspended in 5 ml of water acidified with hydrochloric acid, filtered again, washed with water, and dried to obtain N-(2-dimethylaminocarbonyl- 3-pyridinesulfonyl) -N'-(
4,6-Simethoxy2-pyrimidinyl)thiourea 0
．． 24 g was obtained.

Intermediate Synthesis Example 3 The same method as in Intermediate Synthesis Example 1 was carried out, and the results shown in Table 1 were obtained.

Representative examples of the intermediate compounds represented by the general formula (n) are listed in Table 2.

Next, specific synthesis examples of the compounds of the present invention will be described.

Synthesis Example 1 5,7-Simethoxy-2-(3-dimethylaminocarbonyl-2-thiophenesulfonyl)imino-
Synthesis of 2H-1,2,4-thiadiazolo(2,3-a]pyrimidine (compound Il&ll 26).

N-(3-dimethylaminocarbonyl-2-thiophenesulfonyl) -N'-(4,6-simethoxy2-
0.30 g of (pyridinyl)thiourea was suspended in 14 ml of anhydrous methanol, and 0.12 g of N-bromosuccinimide was added at -5°C or below, followed by stirring at -5°C for 30 minutes to complete the reaction.

After the reaction, solid matter was filtered from the reaction mixture, washed with methanol and dried to obtain the desired product with a melting point of 142-144°C.
3 g was obtained.

Synthesis example 2. 5. Synthesis of 7-Simethoxy 2-(2-dimethylaminocarbonyl-3-pyridinesulfonyl)imino-2H-1,2,4-thiadiazolo(2,3-a]pyrimidine (Compound 11hl 21) N-(2- dimethylaminocarbonyl-3-pyridinesulfonyl)
-N'-(4,6-ditoxy2-pyrimidinyl)thiourea 0.22 g was suspended in 11 ml of anhydrous methanol, and 92 mg of N-bromosuccinimide was added at -5°C or lower.
was added and stirred at -5°C for 1 hour to complete the reaction.

After the reaction, solid matter was filtered from the reaction mixture, washed with methanol and dried to obtain the desired product with a melting point of 173-175°C.
I got g.

Synthesis Example 3 The same method as in Synthesis Example 1 was carried out, and the results shown in Table 3 were obtained.

Representative examples of the compounds of the present invention represented by the general formula (I) are listed in Table 4.

The thiadiazoloazine compound of the present invention exhibits excellent herbicidal effects when used as an active ingredient of a herbicide, as shown in the test examples below.

The herbicide of the present invention can be applied to a wide range of areas other than agricultural land such as rice paddies and fields, as well as lawns, orchards, mulberry orchards, mountain forests, farm roads, grounds, and factory grounds. Process accordingly! ! I can see it.

When the herbicide of the present invention is applied, it is usually mixed with a carrier and, if necessary, various auxiliary agents such as diluents, solvents, emulsifiers, spreading agents, and surfactants to form granules, wettable powders, emulsions, etc. It is used by formulating it as a liquid. The appropriate blending weight ratio of the active ingredient compound and the pesticide adjuvant is generally 0.01:99.99 to 9.
0:10, preferably 0.05:99.95-60
: 40. The appropriate amount to use of the active ingredient compound cannot be unconditionally determined due to differences in weather conditions, soil conditions, drug formulation, target weed type, application time, etc., but in general, 1.
The amount of active ingredient applied per area is 0.03 to 10
0 g, preferably 0.15 to 50 g.

The herbicide of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, soil, phytotoxicity reducers, etc., and in this case may exhibit even better effects and action. When mixed or used in combination with one or more other herbicides, examples of the active ingredients of the herbicides to be mixed include the following.

When applied to rice fields; 2.4-dichlorophenyl-3'-methoxy-4'-nitrophenyl ether, 2.4-dichlorophenyl-3'-methoxycarbonyl-4'-nitrophenyl ether, 2-chloro-2 ',
6'-diethyl-N-(butoxymethyl)acetanilide, 2-chloro-2',6'-diethyl-N-(propoxyethyl)acetanilide, 2-chloro-2',6'-dimethyl-N-(2' −(3
'-methoxy)-thienylmethyl]acetanilide, 5-((2-methyl-1-piperidyl)-carbonylmethyl)-0,0-di-n-propyldithiophosphate, S-<4-:chlorobenzyl)-N , N-diethylthiol carbamate, S-ethyl-hexaε draw IH-azepine-1-carbothioate, S-(1-methyl-1-phenethyl)piperidine-1-
Carbothioate, S-benzyl-N-ethyl-N-(1,2-dimethylpropyl)thiocarbamate, 0-(meta-tert-butylphenyl)-N-methyl-N-(6-medoxypi"lysine-2 -yl)-thiocarbamate, 5-tert-butyl-3-(2,4-dichloro-5
-isopropoxyphenyl)-1,3,4-oxacyapurin-2-one, 2-benzthiazol-2-yloxyacetic acid N-methylanilide, 4-(2,4-dichlorobenzoyl>-i, 3-dimethyl -5-phenacyloxypyrazole, 4-(2,4-
dichlorobenzoyl)-1,3-dimethylpyrazole-
5-yl-p-)luenesulfonate, 4-(2,4-dichloro-3-methylbenzoyl)-1
,3-dimethyl-5-(4-methylphenacyloxy)
pyrazole, 3,7-dichloro-8-quinolinecarboxylic acid, etc.

When applied to corn fields; 3.6-dichloro-2-methoxybenzoic acid, 2.5-dichloro-3-aminobenzoic acid, 2.4-dichlorophenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid, 2 -chloro-
4,6-bis(ethylamino)-1°3.5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-1.3.5- ) riazine, 2-(4-chloro-6
-ethylamino-1,3,5-triazin-2-ylamino)-2-methylpropionitrile, 2-ethylamino-4-isopropylamino-6-methylthio-1,3,5-triazine, 2-chloro- 2',
6'-diethyl-N-(methoxymethyl)acetanilide, 2-chloro-6'-ethyl-N-(2-methoxy-1-
methylethyl)aceto-〇-toluicide, 2-chloro-
N-isopropylacetanilide, 2-chloro-N,N
-Di-2-7'ropenylacetamide, S-ethyl dipropyl thiocarbamate, S-ethyl diisobutyl thiocarbamate, S-propyl dipropyl thiocarbamate, N-(1-ethylpropyl)
-2,6-sinitro 3,4-xylidine, α, α, α-trifluoro 2,6-sinitro N,N
-dipropyl-p-)luidine, 2-(3,5-dichlorophenyl')-2-(2,2,2-trichloroethyl)oxirane, 3-isopropyl-(IH)-benzo-2,1,3-thiadiazine -4-one-2,2-dioxide, 3-(3
, 4-dichlorophenyl)-1-methoxy-1-methylurea, 3,5-dibromo-4-hydroxybenzonitrile, 2-chloro-4-trifluoromethylphenyl-3-ethoxy-4-nitrophenyl ether, and the like.

When applied to soybean fields: Butyl 2- (4-(5-trifluoromethyl-2-
methyl 2-(4-(3-chloro-5-trifluoromethyl-2-pyrisiloxy)phenoxyfupropionate), ethyl 2-(4-(6-chloro-2-benzoxa) Silyloxy]phenoxy]propionate, ethyl 2-
(4-(6-chloro-2-quinoxanyloxy)phenoxyfupropionate, 2-(N-ethoxybutyrimidoyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-1-one , 2-(1-(ethoxyimino)butyl-3-hydroxy-5-thian-3-ylcyclohedis-2-enone, (IE,E)-2-((3-chloro-2-propenyl)
oximinophyl) L5- (2-ethylthiophyl).

lobil)-3-hydroxy-2-cyclohexene-1-
on, N-methoxymethyl-2',6'-diethyl-2-chloroacetanilide, 2-chloro-2'-ethyl-6'-methyl-N-(2-
Methoxy-1-methylethyl)acetanilide, 3-(3,4-dichlorophenyl)-1-methoxy-1
-methylurea, 4-amino-6-tert-butyl-3-methylthio-
1,2,4-triazin-5(4H)-one, 5-[2
-Chloro-4-(trifluoromethyl)phenoxy]-
2-nitrobenzoate sodium salt, 5-[2-chloro-4-(trifluoromethyl)phenoxy)-N-methylsulfonyl-2-nitrobenzamide, and the like.

When applied to wheat fields; Methyl (±) -2-(4-(2,4-dichlorophenoxy)phenoxyfupropionate, 1,2-dimethyl-3,5-diphenyl-IH-pyrazolium methyl sulfate) , ethyl N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate, 4-chlorobuty-
2-ynyl-N-(3-chlorophenyl)-carbamate, 3,5-dibromo-4-hydroxybenzonitrile, 1,2-dimethyl-3,5-diphenyl-IH-pyrazolium methyl sulfate, N-benzoyl-N -(3-chloro-4-fluorophenyl)-2-aminopropionate, ethyl 2,4-dichlorophenoxyacetate, 2-methyl-4-chlorophenoxyacetate, 2-chloro-4,6-bis(ethyl) amino)-S-triazine, 3,5-short-4-octanoyloxybenzonitrile, etc.

When applied to lawn; 2,4-dichlorophenoxyacetic acid (2,4-D), 4-
Chloro-2-methylphenoxyacetic acid (MCP), 2-chloro-4-ethylamino-6-itupropylamino-1
, 3.5-triazine (atrazine), 2-chloro-
4,6-bis(ethylamino)-1゜3.5-triazine (Simazine), 3.5.6-)lichloro-2-pyridyloxyacetic acid (Zytron), Methyl 4-amino-phenylsulfonylcarbamate (Argilan), 3-isopropyl-(IH)-benzo-2,1,3=thiadiazin-4-one-2,2-dioxide (basagran), 3-cyclohexyl-6,7-cyhydro IH-cyclopentapyrimidine-2,4- dione (Renacil), 1-(2-methylcyclohexyl)-3-phenyl urea (Siduron), etc.

In that case, a synergistic effect may also be obtained.

Test Example 1゜1/10.000 A pot was filled with rice paddy soil, and seeds of firefly and tubers of urchin were planted and kept in a moist state. After the firefly grows to 0.5 to 1 leaf stage, about 3
cm, and a hydrating agent of a predetermined compound was diluted with water, and a predetermined amount was added dropwise with a pipette. After 30 days of chemical treatment, the growth condition was observed with the naked eye, and the degree of growth inhibition was evaluated based on the following criteria (5-point scale from 1 to 5), and the results shown in Table 5 below were obtained.

Growth suppression degree 5: Complete suppression state ~ 1: Growth equivalent to untreated area Table 5 Test example 2゜1/10.000 Fill a pot with paddy soil, sow barnyard grass seeds, cover lightly with soil, and then keep quiet. It was flooded to a depth of approximately 3 cm. When barnyard grass germinated, a wettable powder of a given compound was diluted with water, and a given amount was dropped using a pipette. After 24 days of drug treatment, the growth state was observed with the naked eye, and the test example 1
The results were evaluated based on the following criteria and the results shown in Table 6 below were obtained.

Table 6 Test Example 3゜1/10.000 A pot was filled with paddy soil, flooded at about 1 am, and then germinated water cypress was planted.

After the cypress grew to the 1-1.5 leaf stage, it was submerged in water to a depth of approximately 3 cm, and a hydrating agent of a given compound was diluted with water, and a given amount was added dropwise with a pipette. After 28 days of drug treatment, the growth state was visually observed and evaluated based on the criteria of Test Example 1,
The results shown in Table 7 below were obtained.

Table 7 Test Example 4゜1/10,000 are pots were filled with paddy soil, watered and raked, and the next day, 2.5-leaf stage paddy rice (variety: Nipponbare) was transplanted one plant per pot. On the fourth day after transplantation, a hydrating powder of a given compound was diluted with water, and a given amount was dropped using a pipette. After 27 days of drug treatment, the growth status was observed with the naked eye.
Evaluation was made based on the criteria of Test Example 1, and the results shown in Table 8 below were obtained.

Table 8 Note that the compound represented by Compound Magnetic 296 can also be subjected to the same treatments as in Test Examples 1 to 4, and the same results can be obtained.

Test Example 5 Field crop soil was filled in a 1/1,500 are pot, and seeds of various plants were sown. After that, the plants grow at a certain leaf age (soybean early leaf stage, corn 2.5 leaf stage, cotton early leaf stage, Japanese fir 2.5 leaf stage, morning glory 0.5 leaf stage, golden deer 0.5 leaf stage, polygonum 0 .2 leaf stage, Aobiyu 0.3 leaf stage,
When the barnyard grass reached the 2.5 leaf stage, a predetermined amount of the wetting agent of the herbicide of the present invention was weighed out and diluted to 51 parts water per are. Further, an agricultural spreader was added to the aqueous solution to a concentration of 0.2%, and the leaves were treated with a small sprayer. On the 26th day after the treatment, the growth status of various plants was visually observed and surveyed, and the results were graded into 10 stages (l: same as untreated area to 10: completely inhibited).

The degree of growth inhibition was evaluated using the following method (system), and the results shown in Table 9 were obtained.

Table 9 Test Example 6゜The leaf age at the time of chemical treatment was 1.3 leaf stage for soybean and 4 leaf stage for corn.
Leaf stage, cotton 1.2 leaf stage, Japanese fir tree 4 leaf stage, morning moga 2 leaf stage, American red deer 2 leaf stage, knotweed 2 leaf stage, blueberry 2 leaf stage
Leaf stage, barnyard grass 3 leaf stage, and survey date 22 days after treatment.
The results shown in Table 10 were obtained in the same manner as Test Example 5, except for the day.

Table 10 Note that when the compound shown by compound point 54 is subjected to the same treatment as in Test Example 6, it can be expected that similarly good effects will be obtained.

Test Example 7゜The leaf age at the time of chemical treatment was the first leaf stage of soybean, the third leaf stage of corn, the first leaf stage of cotton, the 2.3 leaf stage of Japanese fir tree, and the 2.1 leaf stage of Asagaca
Same as Test Example 5, except that the leaf stage is 1 leaf stage of American kingfisher, 1 leaf stage of Japanese knotweed, 2 leaf stage of Japanese bluegrass, 2.1 leaf stage of Japanese barnyard grass, and the survey date is 12 days after treatment. The results shown in Table 11 were obtained.

Table 11 Note that if the same treatment as in Test Example 6 is applied to the compound shown in Compound No. 54, it can be expected that similarly good effects will be obtained.

Next, formulation examples of the herbicidal composition of the present invention will be described.

Formulation example 1° (11 dicrite 78 parts by weight (2
) Neugen EA-33 (50%) 2 parts by weight (Product name: Dai-Kogyo Seiyaku type) (3) Tsurupol 5060 2 parts by weight (Product name: Toho Chemical Industry type) (4) Tsurupol 5073 3 parts by weight (Product name : Toho Chemical Industries type) (5) Carplex 15 parts by weight (product name: manufactured by Shionogi & Co., Ltd.) Above (mixture of components 11 to (5) and compound ll & 12
99 in a weight ratio of 9:1 to obtain a wettable powder.

Formulation Example 2゜(1) Compound 11h289 0.1 parts by weight (2) Tsurupol 5146 6 parts by weight (
(Product name: Toho Chemical Industry type) (3) Neugen EA-1122 parts by weight (Product name: Dai-Kogyo Seiyaku type) (4) Zikrite 25 parts by weight (
5) Bentonite 66.9 parts by weight or more (11 to (5) are kneaded with a small amount of water, extruded into granules, and dried to form granules.

Formulation example 3゜(1) Kaolin 78 parts by weight (2
) Labelin 8 2 parts by weight (Product name:
(manufactured by Daiichi Kogyo Seiyaku AS) (3) Tsurupol 5039 5 parts by weight (product name: manufactured by Toho Chemical Industries ■) (4) Carplex 15 parts by weight (product name: manufactured by Shionogi & Co., Ltd.) Above (11 to (4) A wettable powder can be obtained by mixing the mixture of the above components and the compound of the present invention in a weight ratio of 8:2.

Formulation Example 4゜+1) High Soiler-11h10. 33 parts by weight (Product name: Matsuzai Sangyo ■) (2) Tsurupol 5050 3 parts by weight (Product name: Toho Chemical ■) (3) Tsurupol 5073 4 parts by weight (Product name: Same as above) (4) Compound 11h126 A wettable powder is obtained by mixing 60 parts by weight or more of each component.

Claims (1)

[Claims] 1. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, J is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, where X is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group,
Alkoxy group, haloalkoxy group, alkoxyalkyl group, haloalkoxyalkyl group, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (R_3 and R_4 are hydrogen atoms or alkyl groups) or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (
R_5 is a hydrogen atom, a cation or an alkyl group), Y is a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group, R_1 and R_2 are an alkyl group,
It is an alkoxy group or a chlorine atom, and Z is -CH= or =
A thiadiazoloazine compound represented by N-, except when R_1 and R_2 are both chlorine atoms. 2. General formula; ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, J is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas, tables, etc. There is ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, where X is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group,
Alkoxy group, haloalkoxy group, alkoxyalkyl group, haloalkoxyalkyl group, ▲ mathematical formula, chemical formula, table, etc. ▼ (R_2 and R_4 are hydrogen atoms or alkyl groups) or -COR_5 (R_5 is a hydrogen atom, cation or is an alkyl group), Y is a hydrogen atom,
a halogen atom, an alkyl group or a haloalkyl group,
R_1 and R_2 are an alkyl group, an alkoxy group, or a chlorine atom, and Z is -CH= or =N-, provided that R
A herbicide characterized by containing as an active ingredient at least one thiadiazoloazine compound represented by the following formula except when _1 and R_2 are both chlorine atoms. 3. General formulas: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, J is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas, tables, etc. ▼, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where X is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group,
Alkoxy group, haloalkoxy group, alkoxyalkyl group, haloalkoxyalkyl group, ▲ mathematical formula, chemical formula, table, etc. ▼ (R_3 and R_4 are hydrogen atoms or alkyl groups) or -COR_5 (R_5 is a hydrogen atom, cation or is an alkyl group), Y is a hydrogen atom,
a halogen atom, an alkyl group or a haloalkyl group,
R_1 and R_2 are an alkyl group, an alkoxy group, or a chlorine atom, and Z is -CH= or =N-, provided that R
In the method for producing a thiadiazoloazine compound represented by the general formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, J, R_1, R_2 and Z are as described above] and an oxidizing agent.