JPH08119948A - Tetrazolinone and its use as a herbicide - Google Patents

Abstract

PURPOSE: To obtain a tetrazolinone which is represented by a specific formula, shows specifically high activity as a herbicide and can be synthesized easily. CONSTITUTION: This compound is represented by formula I (X is a halogen; Y is H, a halogen, a 1-4C alkyl; R<1> is a 1-3C alkyl, R<2> is a substituted 5-6C cycloalkyl, a 5-6C cycloalkenyl, crosslinking cyclic hydrocarbon), for example, 1-(2-chlorophenyl)-4-(perhydroindole-1-yl)carbonyl)5(4H)-tetrazolinone. For example, the compound is preferably obtained by reaction of (A) a compound of formula II such as 1-(2-chlorophenyl)-5(4H)-tetrazolinone with (B) a compound of formula III (hal is chlorine, bromine or another eliminating group) such as N-2-methylcyclohexyl-N-n-ethylcarbamoyl chloride in an inert organic solvent such as pentane, using (C) 4-dimethylaminopyridine as a catalyst or an acid acceptor at about -20 to 130 deg.C.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to tetrazolinones and their use as herbicides. More specifically, the present invention relates to a novel tetrazolinone showing a high activity as a herbicide, a method for producing the same, and use as a herbicide.

[0002]

2. Description of the Related Art It is already known that certain tetrazolinone derivatives have herbicidal activity (JP-A-62-1).
2767, JP 60-146879 A, U.S. Pat. Nos. 4,956,469, 5,019,152 and 5,030,75).

[0003]

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention The present inventors have conducted research to create a novel tetrazolinone derivative showing high herbicidal activity. As a result, a group of novel tetrazolinones represented by the following formula (I) has been obtained. We succeeded in synthesizing the class.

Expression

[0005]

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In the formula, X represents halogen, Y represents a hydrogen atom, halogen or C _1-4 alkyl, R ¹ represents C _1-3 alkyl, and R ² is C _5- substituted by alkyl. ₆ cycloalkyl, C _5-6 cycloalkenyl or a bridged cyclic hydrocarbon group, or R ¹ and R ² together with the N atom to which they are attached form an optionally substituted ring. You may.

The compounds of formula (I) of the present invention are, for example, those of the formula

[0008]

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In the formula, X and Y have the same meanings as described above, and a compound represented by the formula

[0010]

[Chemical 4]

In the formula, R ¹ and R ² are as defined above,
Then, hal is obtained by reacting with a compound represented by a leaving group such as chlorine or bromine.

The compound of the above formula (I) exhibits a strong herbicidal activity and is useful as a herbicide.

As used herein, "halogen" includes fluoro, chloro, bromo and iodo, preferably fluoro, chloro or bromo.

"Alkyl" may be linear or branched and is, for example, methyl, ethyl, n- or i.
so-propyl, n- (iso-, sec- or ter
C _1-6 such as t-) butyl, n-pentyl and n-hexyl
_Including alkyl, among them, C _1-4 alkyl is preferable,
Methyl is especially preferred.

"C _5-6 cycloalkyl" is cyclopentyl and cyclohexyl, and "C _5-6 cycloalkenyl" is 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2
-Including cyclohexenyl and 3-cyclohexenyl,
Preferred are 1-cyclopentenyl, 2-cyclopentenyl, 1-cyclohexenyl and 2-cyclohexenyl.

The "bridged cyclic hydrocarbon group" is a C _4-8 , preferably C _4-7 bridged structure in which two or more aliphatic hydrocarbon rings are covalently bonded to each other in a part of the ring. Including polycyclic groups, particularly preferred are norbornyl and norbornenyl.

In "optionally substituted ring formed together with N atom", said ring contains at least one N atom and optionally at least a heteroatom such as O or S. It may contain one, preferably a 5- or 6-membered monocyclic or condensed polycyclic heterocycle. Then, in formula (I)

[0018]

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Examples of the nitrogen-containing heterocyclic group represented by: piperidino, morpholino, perhydroindole-
1-yl, perhydroquinolin-1-yl, 1-indolinyl and the like are included. And the ring may be optionally substituted, in which case the possible substituents are:
Examples thereof include alkyl such as methyl and ethyl, halogen such as fluoro, chloro, and bromine, and methyl is preferable.

As a preferred group of compounds of the present invention, in the formula (I), X represents fluoro, chloro or bromo, Y represents a hydrogen atom, fluoro, chloro, bromo, methyl or ethyl, and R ¹ is C _5-6 cycloalkyl, which represents methyl, ethyl or n-propyl, and R ² is substituted with methyl or dimethyl, C _5-6 cycloalkenyl,
May represent norbornyl or norbornenyl, or R ¹ and R ² together with the N atom to which they are attached form 2-methylpiperidino, perhydroindol-1-yl or perhydroquinolin-1-yl. , And compounds.

And, as a further preferred group of compounds,
In the above formula (I), X represents chloro or bromo,
Y represents a hydrogen atom, chlorine, bromine or methyl, and R ¹
Represents ethyl or n-propyl, and R ² is methyl-substituted cyclopentyl, methyl- or dimethyl-substituted cyclohexyl, 1-cyclopentenyl, 2-
Cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, 2-norbornyl or 5-norbornene-
2-yl, or R ¹ and R ² are the N to which they are attached.
Taken together with the atoms to form perhydroindol-1-yl or perhydroquinolin-1-yl,
A compound can be mentioned.

In the above-mentioned production method, when 1- (2-chlorophenyl) -5 (4H) -tetrazolinone and (1-chlorocarbonyl) perhydroindole are used as raw materials, the above-mentioned production method is represented by the following reaction formula. To be done.

[0023]

[Chemical 6]

In the above production method, the compound of the formula (II) as a raw material is the Journal of Organic Chemistry Vo.
l. 45, No. 21, 1980, 5130-513
Page 6 or The Journal of American Chemical Society
(The Journal of American Chemical Society) Vol. 81, 1959, 3076-3
It can be synthesized according to the method described on page 079. The following compounds may be mentioned as typical examples of the compound of formula (II).

1- (2-chlorophenyl) -5 (4H)
-Tetrazolinone, 1- (2-chloro-6-methylphenyl) -5 (4H) -tetrazolinone, 1- (2,6-
Dichlorophenyl) -5 (4H) -tetrazolinone and the like.

In the above production method, the raw material of formula (III)
The compound is a compound well known in the field of organic chemistry, and the following compounds can be given as examples.

N-2-methylcyclohexyl-N-ethylcarbamoyl chloride, N-3-methylcyclohexyl-N-ethylcarbamoyl chloride, N-4-methylcyclohexyl-N-ethylcarbamoyl chloride, N-2-methylcyclopentyl-N -N-propylcarbamoyl chloride, N-2-cyclopentenyl-
N-n-propylcarbamoyl chloride, N-2-cyclohexenyl-N-ethylcarbamoyl chloride,
N-2-norbornyl-N-ethylcarbamoyl chloride, N- (5-norbornen-2-yl) -N-ethylcarbamoyl chloride and the like.

The above-mentioned production process can be carried out by reacting the compound of formula (II) with the compound of formula (III) in a reaction-inert organic solvent. Examples of inert organic solvents that may be used in the reaction include aliphatic, cycloaliphatic and aromatic hydrocarbons, which may optionally be chlorinated, such as pentane, hexane,
Cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers such as diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, Dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM); nitriles such as acetonitrile, propionitrile; acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone ,
1,3-Dimethyl-2-imidazolidinone, hexamethylphosphite triamide (HMPA); sulfone, sulfoxides, for example, dimethyl sulfoxide (D
MSO), sulfolane; and bases such as pyridine.

The above-mentioned reaction can be carried out in the presence of an acid binder, and usable acid binders include inorganic metal bases such as alkali metal carbonates and bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate. , Sodium carbonate, potassium carbonate and the like; and as an organic base, tertiary amines, dialkylaminoanilines and pyridines such as triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), N, N- Dimethylaniline, N,
N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), 1,4-diazabicyclo [2,
2,2] octane (DABCO), 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU) and the like can be mentioned.

In addition, 4-dimethylaminopyridine can optionally be used as a catalyst and / or acid binder to synthesize the desired compound.

The above reaction can be carried out within a wide temperature range, but is generally from about -30 to about 200.
It is preferred to carry out at a temperature in the range of ℃, especially about -20 to about 130 ℃. Further, the reaction is preferably carried out under normal pressure, but in some cases, it may be operated under increased pressure or reduced pressure.

Thus, the compound of formula (I) of the present invention is
For example, 1 mol to 1.2 mol of the compound of formula (III) is added to 1 mol of the compound of formula (II) to 1 mol to 1.2 mol.
It can be obtained by reacting in the presence of a molar acid binder and 4-dimethylaminopyridine.

The resulting compound of formula (I) can be isolated and purified by means such as crystallization and chromatography.

The compound of the formula (I) of the present invention has an excellent herbicidal activity as shown in the test examples below, and can be used as a herbicide for controlling weeds. By "weed" herein is meant any plant that grows in undesirable locations.

The compounds of the invention act as non-selective or selective herbicides, depending on the concentration used.

The compound of the present invention can be used as a selective herbicide between the following weeds and cultivated plants, for example.

Dicotyledonous weeds: mustard (Sinapis), bean mung bean soup (Lepidium), yamgrakinutasuta (Ga
lium), chickweed (Stellaria), red sedge (C)
henopodium), nettle (Urtica), hangongsou nobologiku kion (Senecio), huyu hagateu (Ama)
ranthus), purslane lily matsuba button (Portulaca),
Thresher (Xanthium), morning glory (Ipomoea), willow (Polygonum), ragweed (Ambrosia), thistle, Fuji thistle (Cirsium), nogeshi (Sonchus), eggplant
Potato (Solanum), Pepper (Rorippa), Odori Kosou (Lamium), Stag beetle, Spodoptera litura (Ve)
ronica), Japanese morning glory (Datura), violet pansies (Viola), Chishimaodoro (Galeopsis), poppies (Pa
paver), cornflower (Centaurea), yellow cornflower (Galinsoga), yellow cypress (Rotala), azena (Linde
rnia) etc.

Dicotyledonous plants: cotton (Gossypium), soybean (Glycine), chard and sugar beet (Bet)
a), carrot (Daucus), common beans (Phaseolus), peas (Pisum), eggplants (Solanum), flax (Inum), sweet potatoes, morning glory (Ipomoea), broad bean nantenhagi (Vicia), tobacco (Nicotiana) , Tomato (Lycopersicon), peanut (Arachis), rapeseed, cabbage, cabbage, cabbage (Brassica), lacquer beetle (Lactuca), cucumber melon (Cucumis), cactus (Cucurbita), etc.

Monocotyledon weeds: Echinochloa, Echinochloa, Setaria, Millet, Panicum, Digitaria, Pea, Timothy (Phleum), Strawberry Sparrows, Poa, Bosnia serrata (Festuca) , Elephant's millet (Ele
usine), Dokumugi (Lolium), Foxgrass, Inryugi (Bromus), Oat, Oat (Oat) (Av)
ena), Cyperus papyrus, Shichitoui, Cyperus, Sorghum, Duck.
ropyron), eel (Monochoria), tentsuki (Fimbris)
tylis), Omodaka Kwai (Sagittaria), Harry
Kurowai (Eleocharis), firefly, ukiyagra-futoi (Scirpus), pike (Paspalum), platypus (Ischaemum), nukabo (Agrostis), Alopecurus (Alopecurus), cynodon (Cynodon), etc.

Monocotyledonous plants: rice (Oryza), corn / hopcorn (Zea), wheat (Triticum),
Barley (Hordeum), Oats and Oats (Avena), Rye (Secale), Sorghum (Sor)
ghum), millet (Panicum), sugar cane / Vase obana (S
accharum), pineapple (Ananas), asparagus (Asparagus), leeks (Allium), etc.

The use of the compounds according to the invention is not limited to the plants mentioned above, but can be applied to other plants as well. Further, depending on the concentration used, the compound of the present invention is
It can control weeds in a non-selective manner, and can be used, for example, in industrial sites such as factories, railway tracks, roads, plantations, non-plantations, and the like.

Further, the compounds of the present invention can be used for controlling weeds in the cultivation of perennial plants, for example, plantations, ornamental plantations, orchards, vineyards, citrus orchards, nuttsu orchards, Banana plantation, coffee plantation,
It can be applied to tea plantations, rubber plantations, oil palm plantations, cocoa plantations, orchards, hop plantations, etc., and also for selective weed control in the cultivation of annual plants. Can be applied.

The active compounds of the present invention can be made into a usual formulation when used. Examples of the form of such a formulation include liquid preparation, emulsion, wettable powder, suspension, powder, soluble powder, powder, tablet, suspension emulsion concentrate, microcapsule in polymer substance, yanbo formulation and the like. You can

These formulations can be prepared in a manner known per se, for example by adding the active compound to a spreading agent, ie a liquid diluent and / or a solid diluent and, if necessary, surface-active agents. It can be produced by mixing with an agent, that is, an emulsifier and / or a dispersant and / or a foam forming agent.

When water is used as the extender, an organic solvent can be used as an auxiliary solvent. Examples of the liquid diluent include aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride, methylene chloride, etc.) ), Aliphatic hydrocarbons [eg, cyclohexane or paraffins (eg, mineral oil fractions, minerals and vegetable oils)], alcohols (eg, butanol, glycol and ethers and esters thereof), ketones (eg, acetone,
Methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), a strong polar solvent (eg, dimethylformamide, dimethyl sulfoxide, etc.), water and the like can be mentioned.

Examples of solid diluents include ammonium salts, soil natural minerals (for example, kaolin, clay, talc, chiyoke, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.), soil synthetic minerals (for example, highly dispersed silicic acid, alumina). , Silicate, etc.) and the like. Examples of solid carriers for granules include rocks that have been crushed and fractionated (for example, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic particles of inorganic and organic powders, and fine particles of organic materials ( For example, sawdust, coconut coconut, corn cob, tobacco stem, etc.) can be mentioned.

As the emulsifier and / or foaming agent, nonionic and anionic emulsifiers [eg polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers (eg alkylaryl polyglycol ethers, alkyl sulfonates, Alkylsulfates, arylsulfonates, etc.), albumin hydrolysis products, and the like.

Suitable dispersants are, for example, lignin sulfite waste liquor and methylcellulose.

A sticking agent may also be added to the preparation (powder, granule,
Examples of such fixing agents include carboxymethyl cellulose, natural and synthetic polymers (eg, gum arabic, polyvinyl alcohol, polyvinyl acetates, etc.), natural phospholipids (eg, cephalin). And lecithins) and synthetic phospholipids. Furthermore, mineral and vegetable oils can be used as additives.

A coloring agent may be added, and examples of the coloring agent include inorganic pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes such as alizarin dye, azo dye and metal phthalocyanine dye; Mention may be made of trace elements such as salts of metals such as iron, manganese, boron, copper, cobalt, molybdenum, zinc.

The formulations generally contain 0.1 of the active ingredient.
It may be contained in the range of from 95 to 95% by weight, preferably from 0.5 to 90% by weight.

The active compound of the present invention can be used as it is or in the form of a preparation thereof for controlling weeds, and also as a mixture with a known herbicide. May be prepared in advance into the final formulation or may be tank-mixed before use.

Further, the active compound of the present invention can be mixed with a phytotoxicity-reducing agent, and this mixture can broaden the application as a selective herbicide.

Examples of the phytotoxicity reducing agent include 1- (α, α-dimethylbenzyl) -3-p-tolylurea.

The active compound of the present invention may be applied as it is or in the form of the above-mentioned preparation by a conventional method, for example, a method such as watering, spraying, atomizing, dusting or granulating. it can.

The active compounds according to the invention can be applied both before and after germination of the plants. They can also be incorporated into the soil before sowing.

The application rate of the active compound is not strictly limited, it depends on the nature of the desired effect, the target plant,
Although it can be varied over a wide range depending on the application place, application time, etc., as a rough guide, for example, about 0.001 kg to about 1 active compound per hectare is used.
A range of 0 kg, preferably about 0.01 kg to about 5 kg can be exemplified.

Next, the production and use of the compound of the present invention will be explained more specifically with reference to the following examples, but the present invention should not be limited thereto. In addition,
"Parts" means "parts by weight" unless otherwise specified.

[0059]

EXAMPLES Synthesis Example 1

[0060]

[Chemical 7]

1- (2-chlorophenyl) -5 (4H)
4-Tetrazolinone (1.97 g) and (1-chlorocarbonyl) perhydroindole (2.25 g) in toluene (40 ml) in 4-dimethylaminopyridine (1.
59 g) is added and the reaction is carried out at 50 to 55 ° C. for 12 hours. The reaction solution was mixed with 10% hydrochloric acid (20 ml) and then with water (20 ml).
(ml) and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was crystallized with hexane to obtain the desired 1- (2-chlorophenyl) -4- (perhydroindol-1-yl) carbonyl-5 (4H) -tetrazolinone (2.80 g). . mp. 130-131.5
℃ synthesis example 2

[0062]

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1- (2-chlorophenyl) -5 (4H)
-Tetrazolinone (2g), dimethylaminopyridine (1.49g) and N-ethyl-N-2-methylcyclohexylcarbamoyl chloride (2.49g) are dissolved in acetonitrile (30ml) and heated to reflux for 6 hours. After distilling off the solvent under reduced pressure, chloroform (30 ml) is added to the residue and washed with water (20 ml × 2).
The chloroform layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to flash column chromatography (eluent hexane: ethyl acetate = 3: 1) to give the desired 1- (2- Chlorophenyl) -4- (N-ethyl-N-2-methylcyclohexylcarbamoyl)-
5 (4H) -tetrazolinone (1.57 g) is obtained.

N _D ²⁰ 1.5302 Compounds obtained by the same method as in Synthesis Examples 1 and 2 are shown in Table 1 together with the compounds obtained in Synthesis Examples 1 and 2.

[0065]

[Table 1]

[0066]

[Table 2]

[0067]

[Table 3]

[0068]

[Table 4]

Test Example 1 Pre-emergence soil treatment test for upland weeds Preparation method: Carrier: Acetone 5 parts Emulsifier: Benzyloxypolyglycol ether 1 part 1 part Active compound and the above-mentioned amounts of carrier and emulsifier were mixed. , Get the emulsion. A predetermined amount of this emulsion is diluted with water and subjected to the following test.

Test method: In a greenhouse, 120 cm ² pots of field soil were sown on the surface of various pots of Hie and Inubiyu, and the soil was covered with the prescribed amount of the above-mentioned reagent to be uniformly applied to the soil surface of each test pot. Sprinkled on. Four weeks after spraying, the degree of herbicidal effect was examined. The herbicidal effect was evaluated as 100% when completely dead and 0% when it was equivalent to the untreated plot.

Results: Compounds Nos. 1, 8 and 9 were applied to the millet and Amaranthus vulgaris by application of the active ingredient amount of 2 kg / ha.
The herbicidal effect was 100%.

Test Example 2 Post-emergence foliar treatment test for upland weeds Test method: 120 cm filled with upland soil in a greenhouse
² Pots were sown with seeds of millet and Inubiyu to cover the soil. Ten days after sowing, the above Test Example 1 was carried out (weeds were in the average 2 leaf stage).
A predetermined amount of the drug prepared in the same manner as above was uniformly sprayed on the foliage of the test plant of each test pot. The degree of herbicidal effect was investigated 3 weeks after spraying.

Results: Compounds Nos. 1, 8 and 9 showed herbicidal effects of 90% or more on the millet and 80% or more of the millet.

Formulation Example 1 (Granule) To a mixture of 10 parts of Compound No. 1, 30 parts of bentonite (montmorillonite), 58 parts of talc (talc) and 2 parts of lignin sulfonate, 25 parts of water was added and kneaded well. ,
It is made into granules having a size of 10 to 40 mesh by an extrusion type granulator and dried at 40 to 50 ° C to obtain granules.

Formulation Example 2 (Granule) 95 parts of clay mineral particles having a particle size distribution of 0.2 to 2 mm were put in a rotary mixer, and the compound was mixed with a liquid diluent under rotation.
After spraying 5 parts of No.8 to make it even, 40 ~ 50 ℃
Dry with to make granules.

Formulation Example 3 (Emulsion) 30 parts of Compound No. 1, 55 parts of xylene, 8 parts of polyoxyethylene alkylphenyl ether and 7 parts of calcium alkylbenzene sulfonate are mixed and stirred to prepare an emulsion.

Formulation Example 4 (Wettable powder) Compound No. 9 (15 parts), a mixture of white carbon (hydrous amorphous silicon oxide fine powder) and powdered clay (1: 5)
80 parts, 2 parts of sodium alkylbenzene sulfonate and 3 parts of sodium alkylnaphthalene sulfonate formalin condensate are ground and mixed to obtain a wettable powder.

Formulation Example 5 (Hydrated Granule) Compound No. 1 (20 parts), lignin sulfonic acid sodium salt (30 parts), bentonite (15 parts) and calcined diatomaceous earth powder (35 parts) were mixed thoroughly, and water was added to adjust to 0.3 mm. Extrude with a screen and dry to give hydrated granules.

[0079]

INDUSTRIAL APPLICABILITY The novel herbicidal tetrazolinone derivative of the present invention can be easily synthesized by a general production method as shown in Examples, and exhibits an effective action as a herbicide.

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Claims (4)

[Claims] (1) Formula (1) In the formula, X represents halogen, Y represents a hydrogen atom, halogen or C _1-4 alkyl, R ¹ represents C _1-3 alkyl,
And R ² represents C _5-6 cycloalkyl substituted by alkyl, C _5-6 cycloalkenyl or a bridged cyclic hydrocarbon group, or R ¹ and R ² together with the N atom to which they are attached. , A novel tetrazolinone represented by, which may form an optionally substituted ring. 2. X is fluoro, chloro or bromo,
Y represents a hydrogen atom, fluoro, chloro, bromo, methyl or ethyl, R ¹ represents methyl, ethyl or n-propyl, and R ² is a methyl- or dimethyl-substituted C _5-6 cycloalkyl, C _{5- 6 represents} cycloalkenyl, norbornyl or norbornenyl, or R ¹ and R ² together with the N atom to which they are attached form 2-methylpiperidino, perhydroindol-1-yl or perhydroquinolin-1-yl. The compound of claim 1, which may be. 3. X is chlorine or bromine, Y is hydrogen atom, chlorine, bromine or methyl, R ¹ is ethyl or n-propyl, and R ² is methyl-substituted cyclopentyl, methyl or dimethyl. Represents a substituted cyclohexyl, 1-cyclopentenyl, 2-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, 2-norbornyl or 5-norbornen-2-yl, or R ¹ and R ² are attached to each other. 2. N-atoms may be joined together to form perhydroindol-1-yl or perhydroquinolin-1-yl.
Compound of. 4. A herbicide containing the tetrazolinone according to any one of claims 1 to 3 as an active ingredient.