CN1960967A - Triketone-based compound, method for producing the same and herbicide containing the same - Google Patents

Abstract

Disclosed are novel triketone compounds, a method for producing those, and an excellent herbicide containing those. Specifically disclosed are triketone compound represented by the formula (I) below or salts thereof. (I) [In the formula, y is an integer of 1-6; A represents a five-membered or six-membered saturated heterocyclic group containing 1 or 2 hetero atoms selected from the group consisting of an oxygen atom and a sulfur atom, or the like; R<1> represents a halogen; R<2> represents an alkyl, a haloalkyl or the like; R<3>, R<4>, R<6>, R<7> and R<8> respectively represent a hydrogen atom or an alkyl; R<5> represents a hydrogen atom, an alkyl or a cycloalkyl; and Q represents a hydrogen atom or the like].

Description

Trione compounds, its manufacture method and contain the weedicide of this compounds

Technical field

The present invention relates to as the useful new trione compounds of the effective constituent of weedicide, its manufacture method and contain the weedicide of this compounds.

Background technology

Trione compounds as the activeconstituents of weedicide is recorded in patent documentation 1, patent documentation 2 and the patent documentation 3 etc.But its trione compounds with formula of the present invention described later (I) expression is different.

Patent documentation 1: the spy opens flat 6-271562 communique

Patent documentation 2: the spy opens flat 7-206808 communique

Patent documentation 3: international open communique WO2001/14303

Summary of the invention

The objective of the invention is to, provide as the useful new trione compounds of the effective constituent of weedicide, its manufacture method and contain the weedicide of this compounds.

The inventor etc., the result for the trione compounds that may find more excellent weedicide has carried out various researchs has finished the present invention.That is, the present invention relates to trione compounds or its salt, its manufacture method of formula (I) expression and contain the weedicide of this compounds,

[changing 1]

[in the formula, y is 1～6 integer; A contains 1～2 at least a kind of heteroatomic 5 or 6 yuan of saturated heterocyclyl (heterocyclic radical can be replaced by alkyl) or dialkoxy methyl that is selected from the group that Sauerstoffatom and sulphur atom form; R ¹Be halogen; R ²Be alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, alkylthio, halogenated alkylthio, alkyl sulphinyl, haloalkyl sulfinyl, alkyl sulphonyl, halogenated alkyl sulfonyl, dialkyl amino sulfonyl, two (haloalkyl) amino-sulfonyl, nitro or cyano group; R ³, R ⁴, R ⁶, R ⁷And R ⁸Be respectively hydrogen atom or alkyl; R ⁵Be hydrogen atom, alkyl or cycloalkyl, R ⁵And R ⁸Can form 3～6 yuan of saturated carbon rings together, R ⁵And R ⁶Can form ketone together; Q be hydrogen atom ,-C (=O)-(CH ₂) n-R ⁹,-C (=L)-M-R ⁹,-C (=L)-N (R ⁹) R ¹⁰,-SO ₂-N (R ⁹) R ¹⁰, or-SO ₂-R ⁹L and M are respectively Sauerstoffatom or sulphur atom; N is 0～3; R ⁹And R ¹⁰Be respectively hydrogen atom, alkyl, alkoxyalkyl, alkoxyl group, can substituted phenyl or can substituted benzyl; R ⁹And R ¹⁰Can form 5 or 6 yuan of saturated heterocyclyls together; But y is 1, and A is 1, and 3-two  alkane-2-base or 1 is except the occasion of 3-two oxa-s penta ring-2-base].

As R ⁹And R ¹⁰In can substituted phenyl or this substituting group that can substituted benzyl; for example can list halogen, alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, alkylthio, halogenated alkylthio, alkyl sulphinyl, haloalkyl sulfinyl, alkyl sulphonyl, halogenated alkyl sulfonyl, nitro, cyano group etc.This substituent replacement number can be for more than 1 or 2, the occasion more than 2, and each substituting group can be identical or different.In addition, each substituent the position of substitution can be arbitrary position.

R ⁹And R ¹⁰5 or 6 yuan of saturated heterocyclyls can be formed together,, for example pyrrolidyl, piperidyl, morpholinyl etc. can be listed as this saturated heterocyclyl.

As A, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷, R ⁸, R ⁹And R ¹⁰In alkyl or moieties, be respectively the straight or branched alkyl of carbon number 1～6, can list for example methyl, ethyl, propyl group, sec.-propyl, butyl, the tertiary butyl, amyl group, hexyl etc.

As R ⁵In cycloalkyl, be the cycloalkyl of carbon number 3～4, can list for example cyclopropyl, cyclobutyl etc.

As R ¹, R ², R ⁹And R ¹⁰In halogen or halogen part, can list each atom of fluorine, chlorine, bromine or iodine.Replacement number as substituent halogen can be for more than 1 or 2, the occasion more than 2, and each halogen can be identical or different.In addition, the position of substitution of halogen can be arbitrary position.

As 1～2 at least a kind of heteroatomic 5 or 6 yuan of saturated heterocyclyl that is selected from the group that Sauerstoffatom and sulphur atom form that contains among the A, for example can list, tetrahydrofuran (THF)-2-base, tetrahydrofuran (THF)-3-base, two oxa-s, penta ring-2-base, two oxa-s, penta ring-4-base, tetrahydropyrans-2-base, 1,4-two  alkane-2-base, 1,3-two  alkane-2-base, 1,3-two  alkane-4-base, tetramethylene sulfide-2-base, tetrahydric thiapyran-2-base, 1,3-dithiane-2-base, 1,4-dithiane-2-base, 1,4-thiophene  alkane-2-base, 1,4-thiophene  alkane-3-base etc.In addition, this heterocyclic radical can be replaced by the alkyl of carbon number 1～6.

R ⁵And R ⁸Can form 3～6 yuan of saturated carbon rings together, become for example following represented compound of formula.

[changing 2]

R ⁵And R ⁶Can form ketone together, for example become the represented compound of following formula.

[changing 3]

The trione compounds of above-mentioned formula (I) expression, tangible salifiable possibility.As its salt, can comprise all so long as agricultural goes up the salt that allows, for example can list sodium salt, sylvite, the such an alkali metal salt of lithium salts; Magnesium salts, calcium salt, the such alkaline earth salt of barium salt; NH ⁴⁺Ammonium salt that salt, dimethylamine salt, triethylamine salt are such etc.

In the trione compounds of above-mentioned formula (I) expression, have various isomer, for example tautomer, optical isomer etc., comprise in the present invention each isomer and isomer mixture the two.In addition, in the present invention, in the scope of the technology general knowledge of this technical field, also comprise the various isomer beyond above-mentioned.Those skilled in the art in addition,, the situation that becomes the chemical structure different with above-mentioned formula (I) arranged, so long as just can be fully recognized that this is because therefore the relation of isomer is clear and definite within the scope of the invention according to the kind of isomer.

Trione compounds or its salt (hereinafter to be referred as The compounds of this invention) of above-mentioned formula (I) expression can be made according to the manufacture method of following reaction [A]～[E] or common salt.

[changing 4]

In reaction [A], y, A, R ¹, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷And R ⁸As previously described, Hal is a halogen, R ¹¹For-(CH ₂) _n-R ⁹,-M-R ⁹, or-N (R ⁹) R ¹⁰(R ⁹, R ¹⁰, M and n as previously described).

Reaction [A] can be carried out in the presence of alkali and solvent usually.

As alkali, for example can suitably select sodium methylate, sodium ethylate, the such alkali metal alcoholates of potassium tert.-butoxide; Yellow soda ash, the such carbonate of salt of wormwood; Sodium hydride, the such metal hydride of potassium hydride KH; Single methylamine, dimethylamine, the such amine of triethylamine; In pyridines that pyridine, 4-dimethylaminopyridine are such etc. more than a kind or 2 kinds.Can use the compound with respect to formula (I-1) is the alkali of 1～3 times of mole, preferably uses the alkali of 1～2 times of mole.

As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select such aromatic hydrocarbon based of benzene,toluene,xylene, chlorobenzene; Tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, the such aliphatic hydrocarbon of trichloroethane; Two  alkane, tetrahydrofuran (THF), ether, methyl acetate, the such ester class of ethyl acetate; Methyl-sulphoxide, tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone, the such polar aprotic solvent of pyridine; Acetonitrile, the such nitrile of propionitrile; In ketone that acetone, methyl ethyl ketone are such etc. more than a kind or 2 kinds.

The temperature of reaction of reaction [A] is generally-20～+ 50 ℃, is preferably 0～30 ℃, the reaction times, be generally 0.1～12 hour, and be preferably 0.5～2 hour.

[changing 5]

In reaction [B], y, A, R ¹, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷, R ⁸And Hal as previously described, R ¹²For-M-R ⁹Or-N (R ⁹) R ¹⁰(R ⁹, R ¹⁰, M as previously described).

Reaction [B] can be carried out in the presence of alkali and solvent usually.As alkali, in the alkali that for example can suitably select to enumerate in the above-mentioned reaction [A] more than a kind or 2 kinds.Can use the compound with respect to formula (I-1) is the alkali of 1～3 times of mole, and preferred the use is the alkali of 1～2 times of mole.

As solvent, so long as for the solvent of reactionlessness, any can, in the solvent that for example can suitably select to enumerate in the above-mentioned reaction [A] more than a kind or 2 kinds.

The temperature of reaction of reaction [B] is generally 0～100 ℃, is preferably 0～50 ℃, and the reaction times is generally 1～120 hour, is preferably 1～24 hour.

[changing 6]

In reaction [C], y, A, R ¹, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷, R ⁸And Hal as previously described, R ¹³Be R ⁹Or-N (R ⁹) R ¹⁰(R ⁹And R ¹⁰As previously described).

Reaction [C] can be carried out in the presence of alkali and solvent usually.As alkali, in the alkali that for example can suitably select to enumerate in the above-mentioned reaction [A] more than a kind or 2 kinds.Can use the compound with respect to formula (I-1) is the alkali of 1～3 times of mole, and preferred the use is the alkali of 1～2 times of mole.

As solvent, so long as for the solvent of reactionlessness, any can, in the solvent that for example can suitably select to enumerate in the above-mentioned reaction [A] more than a kind or 2 kinds.

The temperature of reaction of reaction [C] is generally 0～50 ℃, is preferably 0～30 ℃, and the reaction times is generally 1～24 hour, is preferably 1～12 hour.

[changing 7]

In reaction [D], y, A, R ¹, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷And R ⁸As previously described.

Reaction [D] can be carried out in the presence of alkali, prussiate and solvent usually.

As alkali, for example can suitably select trialkylamine, trialkanolamine, the such tertiary amines of pyridine; In carbonate that yellow soda ash, salt of wormwood are such etc. more than a kind or 2 kinds.Can use the compound with respect to formula (II) is the alkali of 1～4 times of mole, and preferred the use is the alkali of 2～3 times of moles.

As prussiate, for example can suitably select sodium cyanide, the such alkali metal cyanide of potassium cyanide; In cyanalcohol that acetone cyanohydrin, methyl iso-butyl ketone (MIBK) cyanalcohol, benzaldehyde cyanhydrin, acetaldehyde cyanohydrin, propionic aldehyde cyanalcohol are such etc. more than a kind or 2 kinds.Can use the compound with respect to formula (II) is the cyanogen compound of 0.01～0.5 times of mole, and preferred the use is the cyanogen compound of 0.1～0.2 times of mole.

As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select such aromatic hydrocarbon based of benzene,toluene,xylene, chlorobenzene; Tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane, the such aliphatic hydrocarbon of hexanaphthene; Methyl acetate, the such ester class of ethyl acetate; Methyl-sulphoxide, tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone, the such polar aprotic solvent of pyridine; In nitrile that acetonitrile, propionitrile, vinyl cyanide are such etc. more than a kind or 2 kinds.

Reaction [D] can be carried out in the presence of phase-transfer catalyst as required.As phase-transfer catalyst, can list crown ether-like etc.

The temperature of reaction of reaction [D] is generally 0～50 ℃, is preferably room temperature, the reaction times, be generally 0.5～48 hour, and be preferably 1～24 hour.

[changing 8]

In reaction [E], y, A, R ¹, R ³, R ⁴, R ⁵, R ⁶, R ⁷And R ⁸As previously described, R ¹⁴Be alkyl or haloalkyl, m is 1 or 2.

Reaction [E] can be carried out in the presence of oxygenant and solvent usually.

As oxygenant, for example can suitably select in metachloroperbenzoic acid, hydrogen peroxide, peracetic acid, the tert-butyl hydroperoxide etc. more than a kind or 2 kinds.Can use the compound with respect to formula (I-1) is the oxygenant of 1～5 times of mole, and preferred the use is the oxygenant of 1～3 times of mole.

As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select such aromatic hydrocarbon based of benzene,toluene,xylene, chlorobenzene; Tetracol phenixin, methyl chloride chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane, the such aliphatic hydrocarbon of hexanaphthene; Methyl acetate, the such ester class of ethyl acetate; Methyl alcohol, ethanol, propyl alcohol, the such alcohols of the trimethyl carbinol; Acetate, the such organic acid of propionic acid; In the water etc. more than a kind or 2 kinds.

The temperature of reaction of reaction [E] is generally-20～+ 100 ℃, is preferably-5～+ 50 ℃, the reaction times, be generally 0.1～48 hour, and be preferably 0.1～24 hour.

The compound (enol ester) of the formula of using in above-mentioned reaction [D] (II) can be made according to following reaction [F] or [G].

[changing 9]

In reaction [F], y, A, R ¹, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷And R ⁸As previously described.

Reaction [F] can be carried out in the presence of alkali and solvent usually.

As alkali, for example can suitably select sodium, the such basic metal of potassium; Sodium methylate, sodium ethylate, the such alkali metal alcoholates of potassium tert.-butoxide; Yellow soda ash, the such carbonate of salt of wormwood; Sodium bicarbonate, the such supercarbonate of saleratus; Sodium hydroxide, the such metal hydroxides of potassium hydroxide; Sodium hydride, the such metal hydride of potassium hydride KH; Single methylamine, dimethylamine, the such amine of triethylamine; In pyridines that pyridine, 4-dimethylaminopyridine are such etc. more than a kind or 2 kinds.Can use the compound with respect to formula (IV) is the alkali of 1～3 times of mole, and preferred the use is the alkali of 1～1.5 times of mole.

As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select such aromatic hydrocarbon based of benzene,toluene,xylene, chlorobenzene; Tetracol phenixin, methyl chloride chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane, the such aliphatic hydrocarbon of hexanaphthene; Two  alkane, tetrahydrofuran (THF), the such ethers of ether; Methyl acetate, the such ester class of ethyl acetate; Methyl-sulphoxide, tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone, the such polar aprotic solvent of pyridine; Acetonitrile, propionitrile, the such nitrile of vinyl cyanide; In ketone that acetone, methyl ethyl ketone are such etc. more than a kind or 2 kinds.

The temperature of reaction of reaction [F] is generally 0～50 ℃, is preferably 0～30 ℃, the reaction times, be generally 0.5～24 hour, and be preferably 1～12 hour.

[changing 10]

In reaction [G], y, A, R ¹, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷And R ⁸As previously described.

Reaction [G] can be carried out in the presence of dehydrating condensation agent and solvent usually.

As dehydrating condensation agent, can list for example N, N '-dicyclohexylcarbodiimide etc.Can use with respect to the formula V compound is the dehydrating condensation agent of 1～3 times of mole, and preferred the use is the dehydrating condensation agent of 1～1.5 times of mole.

As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select in such aliphatic hydrocarbon of tetracol phenixin, methyl chloride chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane, hexanaphthene etc. more than a kind or 2 kinds.

The temperature of reaction of reaction [G] is generally 0～50 ℃, is preferably 0～30 ℃, the reaction times, be generally 0.5～48 hour, and be preferably 1～24 hour.

The compound of the formula of using in above-mentioned reaction [F] (IV) can be made according to following reaction [H].

[changing 11]

In reaction [H], y, A, R ¹And R ²As previously described.

Reaction [H] can be carried out in the presence of chlorizating agent usually.As chlorizating agent, can list thionyl chloride, oxalyl chloride etc.Can use the compound with respect to formula V is the chlorizating agent of 1～5 times of mole, and preferred the use is the chlorizating agent of 1～2 times of mole.In addition, if excessive use chlorizating agent, but the double as solvent.

Reaction [H] can be carried out in the presence of solvent as required.As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select such aromatic hydrocarbon based of benzene,toluene,xylene, chlorobenzene; Tetracol phenixin, methyl chloride chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane, the such aliphatic hydrocarbon of hexanaphthene; Two  alkane, tetrahydrofuran (THF), the such ethers of ether; Methyl acetate, the such ester class of ethyl acetate; Acetonitrile, propionitrile, the such nitrile of vinyl cyanide; In ketone that acetone, methyl ethyl ketone are such etc. more than a kind or 2 kinds.

Reaction [H] can be carried out in the presence of catalyzer as required.As catalyzer, can list dimethyl formamide etc.

The temperature of reaction of reaction [H] is generally 0～120 ℃, is preferably 20～100 ℃, the reaction times, be generally 0.5～12 hour, and be preferably 1～4 hour.

The compound of the formula V that uses in above-mentioned reaction [G] or [H] can be made according to following reaction [I].

[changing 12]

In reaction [I], y, A, R ¹And R ²As previously described, R ¹⁵Be alkyl.

Reaction [I] can be carried out according to the general water decomposition reaction that adds, and carries out in the presence of alkali and solvent usually.

As alkali, can list such metal hydroxides of sodium hydroxide for example, potassium hydroxide etc.Can use the compound with respect to formula (VI) is the alkali of 1～5 times of mole, and preferred the use is the alkali of 1～3 times of mole.

As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select acetonitrile, propionitrile, the such nitrile of vinyl cyanide; Acetone, the such ketone of methyl ethyl ketone; Methyl alcohol, ethanol, propyl alcohol, the such alcohols of the trimethyl carbinol; Two  alkane, tetrahydrofuran (THF), the such ethers of ether; In the water etc. more than a kind or 2 kinds.

The temperature of reaction of reaction [I] is generally 0～100 ℃, is preferably 0～30 ℃, the reaction times, be generally 0.1～24 hour, and be preferably 3～20 hours.

The compound of the formula of using in above-mentioned reaction [I] (VI) can be made according to following reaction [J]～[M].

[changing 13]

In reaction [J], y, A, R ¹, R ²And R ¹⁵As previously described, G is hydroxyl, chlorine atom or bromine atoms.

Reaction [J] can be carried out in the presence of solvent usually.As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select such aromatic hydrocarbon based of benzene,toluene,xylene, chlorobenzene; Tetracol phenixin, methyl chloride chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane, the such aliphatic hydrocarbon of hexanaphthene; Two  alkane, tetrahydrofuran (THF), the such ethers of ether; Methyl acetate, the such ester class of ethyl acetate; Methyl-sulphoxide, tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone, the such polar aprotic solvent of pyridine; Acetonitrile, propionitrile, the such nitrile of vinyl cyanide; In the such ketone of acetone, methyl ethyl ketone more than a kind or 2 kinds.

Reaction [J] can be carried out in the presence of alkali as required usually.As alkali, for example can suitably select sodium, the such basic metal of potassium; Sodium methylate, sodium ethylate, the such alkali metal alcoholates of potassium tert.-butoxide; Yellow soda ash, the such carbonate of salt of wormwood; Sodium hydroxide, the such metal hydroxides of hydrogenation oxygen potassium; Sodium hydride, the such metal hydride of potassium hydride KH; Single methylamine, dimethylamine, the such amine of triethylamine; In pyridines that pyridine, 4-dimethylaminopyridine are such etc. more than a kind or 2 kinds.Can be that 1～5 times of mole uses alkali with respect to carboxylic acid cpd, be preferably 1～3 times of mole and use alkali as initial feed.

Reaction [J] can be carried out in the presence of dehydrating condensation agent as required.As dehydrating condensation agent, for example can suitably select among triphenylphosphine, the diethylazodicarboxylate etc. more than a kind or 2 kinds.Can be that 1～5 times of mole uses dehydrating condensation agent with respect to carboxylic acid cpd, be preferably 1～2 times of mole and use dehydrating condensation agent as initial feed.

The temperature of reaction of reaction [J] is generally 0～150 ℃, is preferably 0～120 ℃, and the reaction times is generally 0.5～24 hour, is preferably 1～20 hour.

[changing 14]

In reaction [K], y, A, R ¹, R ¹⁴And R ¹⁵As previously described, D is chlorine atom, bromine atoms or nitro, and E is hydrogen atom or basic metal.

Reaction [K] can be carried out in the presence of solvent usually.As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select such aromatic hydrocarbon based of benzene,toluene,xylene, chlorobenzene; Tetracol phenixin, methyl chloride chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane, the such aliphatic hydrocarbon of hexanaphthene; Two  alkane, tetrahydrofuran (THF), the such ethers of ether; In polar aprotic solvent that methyl-sulphoxide, tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone, pyridine are such etc. more than a kind or 2 kinds.

Reaction [K] can be carried out in the presence of alkali as required.As alkali, for example can suitably select sodium, the such basic metal of potassium; Sodium methylate, sodium ethylate, the such alkali metal alcoholates of potassium tert.-butoxide; Yellow soda ash, the such carbonate of salt of wormwood; Sodium hydroxide, the such metal hydroxides of hydrogenation oxygen potassium; Sodium hydride, the such metal hydride of potassium hydride KH; Single methylamine, dimethylamine, the such amine of triethylamine; In pyridines that pyridine, 4-dimethylaminopyridine are such etc. more than a kind or 2 kinds.Can be that 1～5 times of mole uses alkali with respect to the compound of formula (VI-1), be preferably 1～3 times of mole and use alkali.

The temperature of reaction of reaction [K] is generally 0～150 ℃, is preferably 20～120 ℃, the reaction times, be generally 0.1～72 hour, and be preferably 0.2～24 hour.

[changing 15]

In reaction [L], y, A, R ¹, R ¹⁴, R ¹⁵And m as previously described.

Reaction [L] can be carried out in the presence of oxygenant and solvent usually.

As oxygenant, for example can suitably select in metachloroperbenzoic acid, hydrogen peroxide, peracetic acid, the tert-butyl hydroperoxide etc. more than a kind or 2 kinds.Can be that 1～5 times of mole uses oxygenant with respect to the compound of formula (VI-2), be preferably 1～3 times of mole and use oxygenant.

As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select such aromatic hydrocarbon based of benzene,toluene,xylene, chlorobenzene; Tetracol phenixin, methyl chloride chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane, the such aliphatic hydrocarbon of hexanaphthene; Methyl acetate, the such ester class of ethyl acetate; Methyl alcohol, ethanol, propyl alcohol, the such alcohols of the trimethyl carbinol; Acetate, the such organic acid of propionic acid; In the water etc. more than a kind or 2 kinds.

The temperature of reaction of reaction [L] is generally-20～+ 100 ℃, is preferably-5～+ 50 ℃, the reaction times, be generally 0.1～48 hour, and be preferably 0.1～24 hour.

[changing 16]

In reaction [M], R ¹, R ²And R ¹⁵As previously described, R ¹⁶Be hydrogen atom or alkyl, y ' is 2～6 integer, and p is 0 or 1.

Reaction [M] can be carried out in the presence of acid and solvent usually.

As acid, can list the such organic acid of tosic acid; Mineral acid that sulfuric acid, hydrochloric acid, nitric acid are such etc.

As solvent, so long as for the solvent of reactionlessness, any can, for example can list such aromatic hydrocarbon based etc. of benzene,toluene,xylene, chlorobenzene.

The temperature of reaction of reaction [M] is generally 80～150 ℃, is preferably 100～130 ℃, the reaction times, be generally 0.1～12 hour, and be preferably 0.5～5 hour.

The compound of the formula of using in the above-mentioned reaction [M] (VII) can be made according to following reaction [N].

[changing 17]

In reaction [N], R ¹, R ², R ¹⁵And y ' as previously described, R ¹⁷Be alkyl.Reaction [N] can be carried out in the presence of acid and solvent usually.

As acid, can list such mineral acid of sulfuric acid, hydrochloric acid, nitric acid etc.

As solvent, so long as for the solvent of reactionlessness, any can, for example can suitably select two  alkane, tetrahydrofuran (THF), the such ethers of ether; Acetonitrile, propionitrile, the such nitrile of vinyl cyanide; Acetone, the such ketone of methyl ethyl ketone; Methyl alcohol, ethanol, propyl alcohol, the such alcohols of the trimethyl carbinol; In the water etc. more than a kind or 2 kinds.

The temperature of reaction of reaction [N] is generally 0～100 ℃, is preferably 0～30 ℃, the reaction times, be generally 0.1～12 hour, and be preferably 0.5～4 hour.

The compound of the formula of using in the above-mentioned reaction [N] (IX) can be made according to following reaction [O].

[changing 18]

In reaction [O], R ¹, R ², R ¹⁵, R ¹⁷, y ' and G as previously described.

Reaction [O] can be carried out according to above-mentioned reaction [J].

Compound of the present invention has shown excellent herbicidal effect when using as the effective constituent of weedicide.Its scope of application relates to the many-sides such as non-agricultural cultivated land with road, playground, factory site etc. such as crop land, mountain forest, the agricultural in paddy field, dry land, fruit tree garden, mulberry field etc., and usability methods can select suitably that soil treatment, cauline leaf are handled, retaining is handled.

Compound of the present invention is because can prevent and kill off for example gramineous weeds of barnyard grass, mao matang, Herba Setariae Viridis, Herba Setariae viridis, Herba Eleusines Indicae, wild avena sativa, stone thatch Chinese sorghum, couchgrass, Herba Brachiariae Villoae, Ba Lacao, Semen Euphorbiae, nit grass, annual bluegrass, amur foxtail etc.; The sedge weed of cyperus iria, Rhizoma Cyperi, tiger nuts, firefly Lin, Herba Cyperi Glomerati, Herba Cyperi Difformis, Herba Eleocharitis acicularis, water chestnut etc.; The Alismataceae weeds of short arrowhead, arrowhead, alisma canaliculatum etc.; The Pontederiaceae weeds of Sheathed Monochoria, Monochoria korsakowii etc.; The scrophulariaceae weeds of Procumbent Falsepimpernel, horsefly eye etc.; Mexicana, spend more the Lythraceae weeds of water amaranth etc.; In addition; piemarker; the Pharbitis purpurea flower; lamb's-quarters; the thorn Radix sidae acutae; common purslane; wrinkle fruit amaranth; short luxuriant Amaranthus retroflexus; Cassia tora; black nightshade; pale persicaria; common chickweed; Noogoora burr; the knuckle-tooth bitter cress; benbie; artemisiifolia; Tender Catchweed Bedstraw Herb; Herba seu Flos Convolvuli arvensis; thorn apple; field thistle; the injurious weed of the broadleaf weeds of Herba Acalyphae etc. etc.; so useful crop; corn broomcorn millet for example; soybean; cotton; wheat; rice; barley; oat; jowar; rape; Sunflower Receptacle; beet; sugarcane; cotton grass; peanut; flax; tobacco; in the cultivation of coffee etc., the occasion that can be effective to optionally to prevent and kill off the occasion of injurious weed or non-selectively prevent and kill off injurious weed.Compound of the present invention in the cultivation of corn broomcorn millet, wheat, rice etc., wherein in the cultivation of rice, can be effective to optionally prevent and kill off the occasion of injurious weed especially.

Compound of the present invention can mix with various auxiliarys on the common agricultural, after forming the preparation of forms such as pulvis, granule, particle wettable powder, wettable powder, aqueous suspension agent, oiliness suspension agent, water solvent, emulsion, tablet, capsule, use as weedicide, as long as in the scope that is fit to purpose of the present invention, then can make normally used all preparation forms in this field.As the auxiliary that can in preparation, use, can list the solid carrier of the mixture, clay, yellow soda ash, sodium bicarbonate, saltcake, zeolite, starch etc. of diatomite, slaked lime, lime carbonate, talcum, white carbon(ink), kaolin, wilkinite, kaolinite and sericite; The solvent of water, toluene, dimethylbenzene, solvent naphtha, two  alkane, acetone, isophorone, methyl iso-butyl ketone (MIBK), chlorobenzene, hexanaphthene, methyl-sulphoxide, dimethyl formamide, N-N-methyl-2-2-pyrrolidone N-, alcohol etc.; Soap, benzoate, alkyl sulfo succinate, dialkyl sulfosuccinates, polycarboxylate, alkyl sulfuric ester salt, alkyl-sulphate, alkyl aryl sulfate, alkyl biphenyl sulphate, the alcohol sulfuric acid, alkylsulfonate, alkylaryl sulphonate, arylsulphonate, sulfonated lignin, alkyl diphenyl base ether stilbene-4,4'-bis-(1-azo-3, 4-dihydroxy-benzene)-2,2'-disulfonate, poly styrene sulfonate, alkyl phosphate salt, alkylaryl phosphoric acid salt, the styryl aryl orthophosphate, the Voranol EP 2001 sulfuric acid, polyoxyethylene alkylaryl ether vitriol, the polyoxyethylene alkylaryl ether sulfuric acid, Voranol EP 2001 phosphoric acid salt, polyxyethylated aryl phosphate ester salt, the tensio-active agent of the anionic species that the salt of naphthalene sulfonic acidformaldehyde condensation product is such or developping agent; Sorbitan fatty acid esters, glycerol fatty acid ester, fatty acid polyglycerol ester, the fatty acid alcohol polyglycol ether, acetylenediol ether, acetylene alcohol, the oxyalkylene block polymer, Voranol EP 2001, polyoxyethylene alkylaryl ether, polyoxyethylene styryl aryl ethers, polyoxyethylene glycol alkyl ether, polyoxyethylene fatty acid ester, the polyoxyethylene sorbitan ether fatty acid ester, the polyoxyethylene glycerol fatty acid ester, polyoxyethylene hardened castor oil, the tensio-active agent or the developping agent of the nonionic class that the polyoxypropylene fatty acid ester is such; The vegetables oil or the mineral wet goods of sweet oil, melon baobab oil, Viscotrol C, plam oil, Camellia oil, Oleum Cocois, sesame oil, Semen Maydis oil, Rice pollard oil, Peanut oil, Oleum Gossypii semen, soybean oil, rapeseed oil, Toenol 1140, tung oil, whiteruss etc.These auxiliarys only otherwise break away from purpose of the present invention, can be selected use from the known material in this field.In addition, also can use normally used various auxiliarys such as extender, thickening material, anti-sedimentation agent, frostproofer, dispersion stabilizer, poisoning light-weight additive, mould inhibitor.The compounds of this invention is 0.1: 99.9～95: 5 with the ratio that cooperates of various auxiliarys, is preferably 0.2: 99.8～85: 15.

The amount of application that contains the weedicide of The compounds of this invention, according to the kinds of meteorological conditions, edaphic condition, preparation form, object weeds, use period etc. difference and difference, can not decide without exception, but generally being per 1 hectare, to use The compounds of this invention be 0.5～5000g, be preferably 1～1000g, more preferably 5～500g.The present invention also comprises by using weedicide like this and prevents and kill off the method for injurious weed.

In addition, contain the weedicide of The compounds of this invention, can use with or share, show more excellent effect, functionality in such occasion with other agricultural chemicals, fertilizer, poisoning light-weight additive etc.As other agricultural chemicals, can list weedicide, sterilant, microbiotic, plant hormone, agrochemical.Particularly with the Herbicidal mixture composition of using with or share more than a kind or 2 kinds of the weedicide effective constituent compound of The compounds of this invention and other, can improve the period, weeding activity etc. of the scope that is suitable for grass seeds, chemicals treatment towards preferred direction.In addition, the weedicide effective constituent compound of The compounds of this invention and other can mix the preparation of making respectively when scattering and use, and uses after also both can being made preparation together.The present invention also comprises above-mentioned Herbicidal mixture composition.

The ratio of mixture of The compounds of this invention and other weedicide effective constituent compound, according to the preparation form of meteorological conditions, edaphic condition, medicament, use period, application process etc. difference and difference, can not decide without exception, with respect to 1 weight part The compounds of this invention, cooperating other each effective constituent compound of weedicide is 0.001～10000 weight part, is preferably 0.01～1000 weight part.In addition, use suitable amount and count 0.1～10000g, be preferably 0.2～5000g with per 1 hectare total effective constituent compound amount.The present invention comprises by using such Herbicidal mixture composition and prevents and kill off the method for injurious weed.

As other weedicide effective constituent compound, but the following compound of illustration (popular name comprises the compound in the part application) is under the situation that does not have special record, if when these compounds have salt, alkyl ester etc., then also comprise these salt, alkyl ester etc. certainly.

(1) be considered to show the effective constituent of herbicidal effect by the hormonal action that disturbs plant, as 2,4-D, 2,4-DB, 2,4-DP, MCPA, MCPB, MCPP, the such phenoxy group class of naproanilide (naproanilide); Tribac (2,3,6-TBA), dicamba 98 (dicamba), Niagara 5006 (dichlobenil), picloram (picloram), triclopyr (triclopyr), morpholine acid dichloride picoline (clopyralid), the such aromatic carboxylic acid class of chloro amido pyridine acid (aminopyralid); Other as quinclorac (naptalam), benazolin (benazolin), quinclorac (quinclorac), quinmerac (quinmerac), difluoro pyrrole grand (diflufenzopyr), thiophene halozydine (thiazopyr) etc.

(2) be considered to by suppressing the effective constituent that photosynthesis of plants shows herbicidal effect, the ureas as chlorotoluron (chlorotoluron), Diuron Tech (diuron), fluometuron (fluometuron), methoxydiuron (linuron), isoproturon (isoproturon), chroman grand (metobenzuron), Metribuzin (tebuthiuron); Simazine (simazine), atrazine (atrazine), atraton (atratone), simetryn (simetryn), prometryn (prometryn), penta grass clean (dimethametryn), six piperazines are with (hexazinone), sencorex (metribuzin), terbuthylazine (terbuthylazine), bladex (cyanazine), ametryn (ametryn), cybutryne, third oxygen propylamine Tianjin (triaziflam), the such triazines of propazine (propazine); Bromacil (bromacil), lenacil (lenacil), the such uracil of terbacil (terbacil); Stam F-34 (propanil), encircle the such anilide of careless amine (cypromid); Swep (swep), different phenmedipham (desmedipham), the such amino formate of phenmedipham (phenmedipham); Bromoxynil (bromoxynil), bromoxynil octanoate (bromoxynil-octanoate), the such hydroxy-phenylformonitrile class of ioxynil (ioxynil); Other is as pyridate (pyridate), bentazone (bentazon), amicarbazone (amicarbazone), methazole (methazole) etc.

(3) itself is converted into free radical in plant materials, generates active oxygen, thereby shows the Paraquat of herbicidal effect (paraquat), the such quaternary ammonium salt of diquat (diquat) fast.

(4) by suppressing the biosynthesizing of plant chlorophyll, photosensitive peroxidation material is accumulated in plant materials unusually and shown the effective constituent of herbicidal effect, the diphenylether as nitrofen (nitrofen), chlomethoxynil (chlomethoxyfen), bifenox (bifenox), acifluorfen (acifluorfen-sodium), Fomesafen (fomesafen), Oxyfluorfen (oxyfluorfen), lactofen (lactofen), ethoxyfenethyl ethyl ester (ethoxyfen-ethyl); Chlorphthalim, flumioxazin (flumioxazin), imide phenoxy acetic acid pentyl ester (flumiclorac-pentyl), reach the such cyclin imide class of careless fluorine (fluthiacet-methyl); Other is as the alkynes third  azoles grass (oxadiargyl), oxadiazon (oxadiazon), sulfentrazone (sulfentrazone), fluorine ketazolam grass (carfentrazone-ethyl), thiadiazoles amine (thidiazimin), penta  azoles grass (pentoxazone), azoles pyridine alkynes grass (azafenidin), fluorine bromine azoles ester (isopropazole), fluorine carfentrazone (pyraflufen-ethyl), benzfendizone (benzfendizone), butafenacil (butafenacil), chroman is swelled (metobenzuron), cinidon-ethyl (cinidon-ethyl), amine grass azoles (flupoxam), fluazolate (fluazolate), profluazol (profluazol), pyrachlonil, flufenpyrethyl (flufenpyr-ethyl) etc.

(5) suppress the plant pigments biosynthesizing of carotenoid etc., thereby show with the whitening action to be the effective constituent of the herbicidal effect of feature, the pyridazinone as monometflurazone (norflurazon), chloridazon (chloridazon), metflurazon; Pyrazolate (pyrazolate), pyrazoxyfen (pyrazoxyfen), benzofenap (benzofenap), the such pyrazoles of BAS-670H; Other is as amerol (amitrol), the fluorine grass is with (fluridone), flurtamone (flurtamone), diflufenican (diflufenican), Kayaphenone (methoxyphenone), clomazone (clomazone), sulphur humulone (sulcotrione), nitre sulphur ketone (mesotrione), AVH-301, different  azoles humulone (isoxaflutole), benzene enemy fast (difenzoquat), different  chlorine humulone (isoxachlortole), benzobicylon (benzobicyclone), fluorine pyrrole acyl grass amine (picolinafen), beflubutamid (beflubutamid) etc.

(6) grass is shown the effective constituent of strong specificity herbicidal effect, the aryloxy phenoxy propionic acid class as diclofop-methyl (diclofop-methyl), flampropMmethyl (flamprop-M-methyl), pyriphenop-sodium, fluazifop (fluazifop-butyl), pyrrole fluorine chlorine standing grain spirit (haloxyfop-methyl), quizalofop (quizalofop-ethyl), cyhalofop-butyl (cyhalofop-butyl),  azoles diclofop-methyl (fenoxaprop-ethyl), metamifop-propyl; Cyclohexyl diketone that alloxydim (alloxydim-sodium), clethodim (clethodim), sethoxydim (sethoxydim), tralkoxydim (tralkoxydim), fourth oxygen cyclic ketones (butroxydim), quinone oximes grass (tepraloxydim), caloxydim, AC322140 (clefoxydim), clefoxidim (profoxydim) are such etc.

(7) by suppressing the effective constituent that the plant amino acid biosynthesizing shows herbicidal effect, as chlorimuronethyl (chlorimuron-ethyl), sulfometuronmethyl (sulfometuron-methyl), primisulfuronmethyl (primisulfuron-methyl), benbbensulfuronmethyl (bensulfuron-methyl), green sulphur swells (chlorsulturon), metsulfuronmethyl (metsulfuron-methyl), cinosulfuron (cinosulfuron), pyrazosulfuronmethyl (pyrazosulfuron-ethyl), azimsulfuron (azimsulfuron), flazasulfuron (flazasulfuron), rimsulfuron (rimsulfuron), nicosulfuron (nicosulfuron), imazosulfuron (imazosulfuron), AC322140 (cyclosulfamuron), prosulfuron (prosulfuron), flupyrsulfuronmethylsodium (flupyrsulfuron), trisulfuron-methyl, halosulfuronmethyl (halosulfuron-methyl), thifensulfuron methyl (thifensulfuron-methyl), ethoxysulfuron (ethoxysulfuron), oxasulfuron (oxasulfuron), ethametsulfuron (ethametsulfuron), fluorine flazasulfuron (flupyrsulturon), iodine sulphur swells (iodosulfuron), sulfosulfuron (sulfosulfuron), triasulfuron (triasulfuron), tribenuron-methyl (tribenuron-methyl), tritosulfuron (tritosulfuron), foramsulfuron (foramsulfuron), trifloxysulfuron (trifloxysulfuron), isosulfuron-methyl, fluorine pyrrole sulphur swells (flucetosulfuron), the such sulfonylurea of mesosulfuronmethyl (mesosulfuron-methyl); Fluorine ethofumesate (flumetsulam), azoles grass sulfanilamide (SN) (metosulam), the phonetic sulfanilamide (SN) of azoles (diclosulam), cloransulammethyl (cloransulam-methyl), florasulam (florasulam), metosulfam, the such triazolopyrimidine sulfonamides of penoxsuam (penoxsulam); Weed eradication cigarette (imazapyr), Imazethapyr (imazethapyr), weed eradication quinoline (imazaquin), imazamox (imazamox), miaow cigarette azoles grass (imazameth), miaow grass ester (imazamethabenz), the such imidazolone type of AC 263222 (imazapic); Pyrithiobacsodium (pyrithiobac-sodium), two KIH 6127 (bispyribac-sodium), KIH 6127 (pyriminobac-methyl), pyribenzoxim (pyribenzoxim), pyriftalid (pyriftalid), the such pyrimidyl salicylic acid of KUH-021; Flucarbazonesodium (flucarbazone), the such sulfonyl amino carbonyl triazolineone of procarbazone (procarbazone-sodium); Other is as glyphosate (glyphosate), ammonium glyphosate (glyphosate-ammonium), glyphosate isopropyl amine (glyphosate-isopropylamine), sulphosate (sulfosate), gulfosinate, careless ammonium phosphine (glufosinate-ammonium), bilanafos (bialaphos) etc.

(8) by suppressing the effective constituent that plant cell mitosis shows herbicidal effect, the dinitroaniline as trifluralin (trifluralin), oryzalin (oryzalin), nitralin (nitralin), pendimethalin (pendimethalin), fourth fluchloralin (ethalfluralin), benfluralin (benfluralin), prodiamine (prodiamine); Amides as bensulide (bensulide), R-7465 (napronamide), pronamide (pronamide); Amiprophosmethl (amiprofos-methyl), butamifos (butamifos), anilofos (anilofos), the such organic phosphates of piperophos (piperophos); Propham (propham), Y 3 (chlorpropham), the such phenylcarbamate class of Herba ainsliaeae yunnanensis (barban); Daimuron (daimuron), cumyluron (cumyluron), the such cumenyl amine of bromobutide (bromobutide); Other is as asulam (asulam), dithiopyr (dithiopyr), thiazopyr (thiazopyr) etc.

(9) by protein biosynthesizing that suppresses plant or the effective constituent that the lipid biosynthesizing shows herbicidal effect, the chloroacetyl amine as alachlor (alachlor), Butachlor technical 92 (butachlor), the third careless amine (pretilachlor), metolachlor (metolachlor), S-metolachlor (S-metolachlor), P DimethenamidP (thenylchlor), pethoxamid (pethoxamid), acetochlor (acetochlor), propachlor (propachlor), propisochlor (propisochlor); Other are as ethobenzanid (etobenzanid), mefenacet (mefenacet), flufenacet (flufenacet), tridiphane (tridiphane), cafenstrole (cafenstrole), fentrazamide (fentrazamide),  piperazine humulone (oxaziclomefone), indanofan (indanofan), dimethenamid (dimethenamid) etc.

(10) thiocarbamates as EPTC, butylate (butylate), vernolate (vernolate), Hydram (molinate), pebulate (pebulate), cycloate (cycloate), dimepiperate (dimepiperate), weed eradication fear (prosulfocarb), esprocarb (esprocarb), thiobencarb (thiobencarb), pyributicarb (pyributicarb), di_allate (diallate), tri_allate (triallate); Other kill (endothall), ethofumesate (ethofumesate), sodium chlorate (sodium chlorate), n-nonanoic acid (pelargonic acid) more, kill wooden phosphorus (fosamine), pinoxaden, HOK-201 etc. as MSMA, DSMA, mattress.

(11) by colonizing in the activeconstituents that shows herbicidal effect on the plant, as the edible wild herbs Xanthomonas campestris ( Xanthomonas Campestris), Epicoccosurus Nematosurus, Exserohilum Monoseras, Drechsrela MonocerasDeng.

In addition, The compounds of this invention has security for the crop of rice, wheat, corn broomcorn millet etc., and, contain and shown the optionally compound of management of weeds well, when in above-mentioned arable farming, using The compounds of this invention, in above-mentioned other the effective constituent compound of weedicide, if use with or and with in the following compound for example more than a kind or 2 kinds, can obtain synergy.

The cultivation of rice: 2,4-D, MCPA, MCPB, naproanilide (naproanilide), quinclorac (quinclorac), simetryn (simetryn), prometryn (prometryn), penta grass clean (dimethametryn), Stam F-34 (propanil), swep (swep), bentazone (bentazon), nitrofen (nitrofen), chlomethoxynil (chlomethoxyfen), bifenox (bifenox), the alkynes third  azoles grass (oxadiargyl), oxadiazon (oxadiazon), sulfentrazone (sulfentrazone), fluorine ketazolam grass (carfentrazone-ethyl), penta  azoles grass (pentoxazone), pyrazolate (pyrazolate), pyrazoxyfen (pyrazoxyfen), benzofenap (benzofenap), Kayaphenone (methoxyphenone), cyhalofop-butyl (cyhalofop-butyl), benbbensulfuronmethyl (bensulfuron-methyl), cinosulfuron (cinosulfuron), pyrazosulfuronmethyl (pyrazosulfuron-ethyl), azimsulfuron (azimsulfuron), imazosulfuron (imazosulfuron), AC322140 (cyclosulfamuron), ethoxysulfuron (ethoxysulfuron), two KIH 6127 (bispyribac-sodium), KIH 6127 (pyriminobac-methyl), anilofos (anilofos), piperophos (piperophos), daimuron (daimuron), cumyluron (cumyluron), bromobutide (bromobutide), dithiopyr (dithiopyr), Hydram (molinate), dimepiperate (dimepiperate), esprocarb (esprocarb), thiobencarb (thiobencarb), pyributicarb (pyributicarb), P DimethenamidP (thenylchlor), the third careless amine (pretilachlor), Butachlor technical 92 (butachlor), ethobenzanid (etobenzanid), mefenacet (mefenacet), flufenacet (flufenacet), cafenstrole (cafenstrole), fentrazamide (fentrazamide),  piperazine humulone (oxaziclomefone), indanofan (indanofan), benzobicylon (benzobicyclone), pyribenzoxim (pyribenzoxim), third oxygen propylamine Tianjin (triaziflam), clefoxidim (clefoxydim), pyraclonil (pyraclonil), pyriftalid (pyriftalid).

The cultivation of corn broomcorn millet: 2,4-D, MCPA, dicamba 98 (dicamba), morpholine acid dichloride picoline (clopyralid), benazolin (benazolin), the difluoro pyrrole swells (diflufenzopyr), Diuron Tech (diuron), methoxydiuron (linuron), chroman is swelled (metobenzuron), simazine (simazine), atrazine (atrazine), atraton (atratone), sencorex (metribuzin), terbuthylazine (terbuthylazine), bladex (cyanazine), ametryn (ametryn), encircle careless amine (cypromid), bromoxynil (bromoxynil), bromoxynil octanoate (bromoxynil-octanoate), the grass of rattling away ends (pyridate), bentazone (bentazon), Paraquat (paraquat), Oxyfluorfen (oxyfluorfen), imide phenoxy acetic acid pentyl ester (flumiclorac-pentyl), reach careless fluorine (fluthiacet-methyl), the fluorine grass is with (fluridone), sulphur humulone (sulcotrione), nitre sulphur ketone (mesotrione), different  chlorine humulone (isoxachlortole), fluorine ketazolam grass (carfentrazone-ethyl), primisulfuronmethyl (primisulfuron-methyl), rimsulfuron (rimsulfuron), nicosulfuron (nicosulfuron), prosulfuron (prosulfuron), pyrazosulfuronmethyl (halosulfuron-methyl), chlorine thifensulfuron methyl (thifensulfuron-methyl), fluorine ethofumesate (flumetsulam), azoles grass sulfanilamide (SN) (metosulam), Imazethapyr (imazethapyr), ammonium glyphosate (glyphosate-ammonium), glyphosate isopropyl amine (glyphosate-isopropylamine), grass ammonium phosphine (glufosinate-ammonium), trifluralin (trifluralin), pendimethalin (pendimethalin), EPTC, butylate (butylate), alachlor (alachlor), metolachlor (metolachlor), S-metolachlor (S-metolachlor), acetochlor (acetochlor), propachlor (propachlor), dimethenamid (dimethenamid), tridiphane (tridiphane), florasulam (florasulam), chroman is swelled (metobenzuron), メ ト ス Le Off ア Application, oxasulfuron (oxasulfuron), quinone oximes grass (tepraloxydim), amicarbazone (amicarbazone), foramsulfuron (foramsulfuron).

The cultivation of wheat: MCPB; quinmerac (quinmerac); methoxydiuron (linuron); isoproturon (isoproturon); prometryn (prometryn); bromoxynil (bromoxynil); bromoxynil octanoate (bromoxynil-octanoate); the grass of rattling away ends (pyridate); bifenox (bifenox); fluorine ketazolam grass (carfentrazone-ethyl); thiadiazoles amine (thidiazimin); fluorine carfentrazone (pyraflufen-ethyl); flurtamone (flurtamone); diflufenican (diflufenican); sulphur humulone (sulcotrione); diclofop-methyl (diclofop-methyl); tralkoxydim (tralkoxydim); green sulphur swells (chlorsulfuron); metsulfuronmethyl (metsulfuron-methyl); prosulfuron (prosulfuron); halosulfuronmethyl (halosulfuron-methyl); fluorine ethofumesate (flumetsulam); azoles grass sulfanilamide (SN) (metosulam); pendimethalin (pendimethalin); Herba ainsliaeae yunnanensis (barban); miaow grass ester (imazamethabenz); cinidon-ethyl (cinidon-ethyl); ethoxyfenethyl ethyl ester (ethoxyfen-ethyl); florasulam (florasulam); fluazolate (fluazolate); amine grass azoles (flupoxam); iodine sulphur swells (iodosulfuron); メ ト ス Le Off ア system; pyribenzoxim (pyribenzoxim); sulfosulfuron (sulfosulfuron); tralkoxydim (tralkoxydim); flucarbazonesodium (flucarbazone-sodium); fluorine pyrrole acyl grass amine (picolinafen); AC322140 (cyclosulfamuron); ethoxysulfuron (ethoxysulfuron); imazamox (imazamox); beflubutamid (beflubutamid); flucarbazonesodium (flucarbazone); procarbazone (procarbazone-sodium).

Preferred configuration of the present invention is as described below.

(1) Q be hydrogen atom ,-C (=O)-(CH ₂) _n-R ⁹,-C (=O)-M-R ⁹,-C (=O)-N (R ⁹) R ¹⁰,-SO ₂-N (R ⁹) R ¹⁰Or-SO ₂-R ⁹The compound or its salt of above-mentioned formula (I).

(2) Q be hydrogen atom ,-C (=O)-(CH ₂) _n-R ⁹,-C (=O)-M-R ⁹Or-SO ₂-R ⁹The compound or its salt of above-mentioned formula (I).

(3) Q be hydrogen atom or-C (=O)-(CH ₂) _n-R ⁹The compound or its salt of above-mentioned formula (I).

(4) R ⁹And R ¹⁰Be respectively hydrogen atom, alkyl, can substituted phenyl wantonly 1 compound or its salt of above-mentioned (1)～(3).

(5) Q is the compound or its salt of the above-mentioned formula (I) of hydrogen atom.

(6) A contains 1～2 wantonly 1 compound or its salt that is selected from above-mentioned (1)～(5) of at least a kind of heteroatomic 5 or 6 yuan of saturated heterocyclyl (heterocyclic radical can be replaced by alkyl) in the group that Sauerstoffatom and sulphur atom form or dialkoxy methyl.

(7) A contains 1～2 wantonly 1 compound or its salt that is selected from above-mentioned (1)～(5) of at least a kind of heteroatomic 5 or 6 yuan of saturated heterocyclyl (heterocyclic radical can be replaced by alkyl) in the group that Sauerstoffatom and sulphur atom form.

(8) A is wantonly 1 compound or its salt of above-mentioned (1)～(5) that contains 5 or 6 yuan of saturated heterocyclyls (heterocyclic radical can be replaced by alkyl) of 1～2 Sauerstoffatom.

(9) A is wantonly 1 compound or its salt of above-mentioned (1)～(5) that contains 5 yuan of heterocyclic radicals (heterocyclic radical can be replaced by alkyl) of 1～2 Sauerstoffatom.

(10) A is wantonly 1 compound or its salt of above-mentioned (1)～(5) that contains 5 yuan of saturated heterocyclyls (heterocyclic radical can be replaced by alkyl) of 2 Sauerstoffatoms.

(11) R ²Wantonly 1 compound or its salt for above-mentioned (1)～(10) of haloalkyl, halogenated alkoxy, alkylthio, alkyl sulphinyl, alkyl sulphonyl, dialkyl amino sulfonyl, nitro or cyano group.

(12) R ²Wantonly 1 compound or its salt for above-mentioned (1)～(10) of haloalkyl, alkylthio, alkyl sulphinyl, alkyl sulphonyl, nitro or cyano group.

(13) R ²Wantonly 1 compound or its salt for above-mentioned (1)～(10) of alkylthio, alkyl sulphinyl or alkyl sulphonyl.

(14) R ²Wantonly 1 compound or its salt for above-mentioned (1)～(10) of alkyl sulphonyl.

(15) y is wantonly 1 compound or its salt of above-mentioned (1)～(14) of 2～6 integer.

(16) y is wantonly 1 compound or its salt of 2 or 3 above-mentioned (1)～(14).

(17) y is wantonly 1 compound or its salt of 2 above-mentioned (1)～(14).

(18) R ³, R ⁴, R ⁶, R ⁷And R ⁸Be respectively wantonly 1 compound or its salt of above-mentioned (1)～(17) of hydrogen atom or methyl.

(19) R ³, R ⁴, R ⁶, R ⁷And R ⁸Be respectively wantonly 1 compound or its salt of above-mentioned (1)～(17) of hydrogen atom.

(20) contain the weedicide of wantonly 1 compound or its salt of above-mentioned (1)～(19) as effective constituent.

(21) use the method for preventing and kill off noxious plant of wantonly 1 compound or its salt of above-mentioned (1)～(19) of herbicidally effective amount.

Embodiment

Following notebook inventive embodiment, but the present invention is not limited to this.At first, the synthesis example of record The compounds of this invention.

Synthesis example 1

2-[[2 '-chloro-3 '-[2-(1,3-two oxa-s penta ring-2-yl) oxyethyl group]-4 '-methyl sulphonyl benzoyl]]-1,3-cyclohexanedione (the aftermentioned compound N is o.1-8) synthetic

(1) to 5.0g2, in the mixture of 4-two chloro-3-methyl hydroxybenzoates and 30ml dimethyl formamide, add 6.14g2-(2-bromotrifluoromethane)-1,3-two oxa-s penta ring and 6.25g salt of wormwood reacted 1.5 hours down at 110 ℃.Reaction mixture is put in the water, with washing after the extracted with diethyl ether.With concentrating under reduced pressure behind the anhydrous magnesium sulfate drying organic layer, with residue silica gel column chromatography (elutriant: refining ethyl acetate/normal hexane=1/9), obtain 5.45g buttery 2,4-two chloro-3-[2-(1,3-two oxa-s penta ring-2-yl) oxyethyl group] methyl benzoate.The NMR spectrum of this material is as described below.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

2.23-2.45(m，2H)，3.87-3.95(m，5H)，3.98-4.0(m，2H)，4.18(t，2H)，5.19(t，1H)，7.33(d，1H)，7.51(d，1H)

(2), 4-two chloro-3-[2-(1,3-two oxa-s penta ring-2-yl) oxyethyl group to 5.45g2] add 1.19 sodium methyl mercaptides in the mixture of methyl benzoate and 30ml dimethyl formamide, 50 ℃ of reactions 15 minutes down.Reaction mixture is put in the water, with washing after the extracted with diethyl ether.With concentrating under reduced pressure behind the anhydrous magnesium sulfate drying organic layer, with residue at silica gel column chromatography (elutriant: refining ethyl acetate/normal hexane=1/9), obtain 3.4g buttery 2-chloro-3-[2-(1,3-two oxa-s penta ring-2-yl) oxyethyl group]-4-methyl thiobenzoic acid methyl esters.The NMR spectrum of this material is as described below.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz) 2.22-2.28 (m, 2H), 2.44 (s, 3H), 3.85-3.92 (m, 5H), 3.96-4.01 (m, 2H), 4.16 (t, 2H), 5.20 (t, 1H), 7.01 (d, 1H), 7.60 (d, 1H)

(3) to 3.4g 2-chloro-3-[2-(1,3-two oxa-s penta ring-2-yl) oxyethyl group]-mixture of 4-methylthio-benzoic acid methyl esters and 60ml chloroform in, the ice-cold 4.85g metachloroperbenzoic acid that adds down was back under the room temperature reaction 15 hours.Filter reaction mixture is used the wet chemical wash filtrate, then washing.With concentrating under reduced pressure behind the anhydrous sodium sulfate drying, obtain 4.2g buttery 2-chloro-3-[2-(1,3-two oxa-s penta ring-2-yl) oxyethyl group]-4-methyl sulphonyl methyl benzoate.The NMR spectrum of this material is as described below.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz) 2.28-2.34 (m, 2H), 3.25 (s, 3H), 3.87-3.92 (m, 2H), 3.96-4.05 (m, 5H), 4.40 (t, 2H), 5.16 (t, 1H), 7.63 (d, 1H), 7.92 (d, 1H)

(4) to 4.2g2-chloro-3-[2-(1,3-two oxa-s penta ring-2-yl) oxyethyl group]-mixture of 4-methyl sulphonyl methyl benzoate and 60ml tetrahydrofuran (THF) in, add the mixture of 1.84g sodium hydroxide and 30ml water, at room temperature reacted 15 hours.In reaction mixture, add water, wash with methylene dichloride.It is acid making water layer with hydrochloric acid, uses anhydrous magnesium sulfate drying behind the ethyl acetate extraction again, and behind the concentrating under reduced pressure, acquisition 3.76g fusing point is 142～144 ℃ 2-chloro-3-[2-(1,3-two oxa-s penta a ring-2-yl) oxyethyl group]-4-sulfonyloxy methyl yl benzoic acid.

(5) to 3.76g2-chloro-3-[2-(1; 3-two oxa-s penta ring-2-yl) oxyethyl group]-4-sulfonyloxy methyl yl benzoic acid, 1.44g1; in the mixture of 3-cyclohexanedione and 50ml methylene dichloride, ice-cold 2.43gN, the mixture of N '-dicyclohexylcarbodiimide and 30ml methylene dichloride of dripping down.After dripping termination, be back under the room temperature and reacted 15 hours.Filter reaction mixture is used the wet chemical wash filtrate, uses anhydrous sodium sulfate drying after the washing again, behind the concentrating under reduced pressure, obtains the 4.8g enol ester.

(6) in the mixture of enol ester that in the above-mentioned operation of 4.8g, obtains and 50ml acetonitrile, add 2.16g triethylamine and 0.23g acetone cyanohydrin, at room temperature reacted 4 hours.Filter reaction mixture concentrates back adding methylene dichloride with filtrate decompression and wet chemical carries out separatory.It is acid making water layer with hydrochloric acid, with using anhydrous sodium sulfate drying behind the dichloromethane extraction again, behind the concentrating under reduced pressure, obtains the object of 3.68g malt sugar shape.

Synthesis example 2

2-[[2 '-chloro-3 '-[2-(4-methyl isophthalic acid, 3-two oxa-s penta ring-2-yl) oxyethyl group]-4 '-methyl sulphonyl benzoyl]]-1,3-cyclohexanedione (the aftermentioned compound N is o.1-10) synthetic

(1) to 0.5g2,4-two chloro-3-methyl hydroxybenzoates, 0.36g2-(4-methyl isophthalic acid, 3-two oxa-s penta ring-2-yl) in the mixture of ethanol, 0.89g triphenylphosphine and 15ml tetrahydrofuran (THF), the ice-cold mixture that drips 1.23g diethylazodicarboxylate and 5ml tetrahydrofuran (THF) down.After dripping termination, be back under the room temperature and reacted 15 hours.Concentrating under reduced pressure behind the washed reaction mixture, with residue silica gel column chromatography (elutriant: refining ethyl acetate/normal hexane=1/9), obtain 0.67g buttery 2,4-two chloro-3-[2-(4-methyl isophthalic acid, 3-two oxa-s penta ring-2-yl) oxyethyl group] methyl benzoate.The NMR spectrum of this material is as described below.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz) 1.26-1.31 (m, 3H), 2.22-2.28 (m, 2H), 3.43 (q, 1H), 3.92 (s, 3H), 3.96-4.0 (m, 1H), 4.15-4.21 (m, 3H), 5.22 (t, 1H), 7.34 (d, 1H), 7.51 (d, 1H)

(2), 4-two chloro-3-[2-(4-methyl isophthalic acid, 3-two oxa-s penta ring-2-yl) oxyethyl group with 0.67g 2] methyl benzoate is as starting raw material, according to the method for above-mentioned synthesis example 1 (2)～(6), obtains the object of 0.32g malt sugar shape.

Synthesis example 3

2-[[2 '-chloro-3 '-[2-(1,3-two oxa-s penta ring-2-yl) oxyethyl group]-4 '-methyl sulphonyl benzoyl]]-3-benzoyloxy-2-tetrahydrobenzene-1-ketone (the aftermentioned compound N is o.1-48) synthetic

To 0.3g according to above-mentioned synthesis example 1 synthetic 2-[[2 '-chloro-3 '-[2-(1; 3-two oxa-s penta ring-2-yl) oxyethyl group]-4 '-the methyl sulphonyl benzoyl]]-1; in the mixture of 3-cyclohexanedione and 10ml ethylene dichloride; after adding 0.1g triethylamine and 0.95g benzoyl chloride, at room temperature reacted 1.5 hours.The washed reaction mixture is used concentrating under reduced pressure behind the anhydrous sodium sulfate drying organic layer again, obtains 0.37g buttery object.

Synthesis example 4

2-[[2 '-chloro-3 '-(3,3-diethoxy propoxy-)-4 '-methyl sulphonyl benzoyl]-1,3-cyclohexanedione (the aftermentioned compound N is o.1-39) synthetic

In the operation (1) of above-mentioned synthesis example 1, except using 3-chloro-1, the 1-di ethyl propyl ether replaces 2-(2-bromotrifluoromethane)-1, beyond 3-two oxa-s penta ring, according to the method for above-mentioned synthesis example 1, obtains 1.2g buttery object.

Then, enumerate the typical example of the The compounds of this invention of above-mentioned formula (I) expression in the 1st～5 table, enumerate its rerum natura in the 6th～7 table, these compounds can synthesize according to the various manufacture method of above-mentioned synthesis example or the invention described above compound.In addition, in table, represent that with Me methyl, Et represent that ethyl, Pr represent that propyl group, Ph represent phenyl respectively.In addition, in table, 2-Me-Ph is illustrated in 2 methyl substituted phenyl, and other same records are also like this.

[changing 19]

Table 1

Compound N o.	R 1	R 2	Q	y	A
						1-1	Cl	SO 2Me	H	1	A-4
1-2	Cl	SO 2Me	H	1	A-6
						1-3	Cl	SO 2Me	H	1	A-10
1-4	Cl	SO 2Me	H	1	A-12
						1-5	Cl	NO 2	H	1	A-1
1-6	Cl	NO 2	H	1	A-2
						1-7	Cl	NO 2	H	1	A-7
1-8	Cl	SO 2Me	H	2	A-3
						1-9	Cl	SO 2Me	H	2	A-4
1-10	Cl	SO 2Me	H	2	A-5
						1-11	Cl	SO 2Me	H	2	A-6
1-12	Cl	SO 2Me	H	2	A-7
						1-13	Cl	SO 2Me	H	2	A-8
1-14	Cl	SO 2Me	H	2	A-9
						1-15	Cl	SO 2Me	H	2	A-10
1-16	Cl	SO 2Me	H	2	A-11
						1-17	Cl	SO 2Me	H	2	A-12
1-18	Cl	SO 2Me	H	2	A-13
						1-19	Cl	SO 2Me	H	2	A-14
1-20	Cl	SO 2Me	H	2	A-15
						1-21	Cl	SO 2Me	H	2	A-16
1-22	Cl	SO 2Et	H	2	A-3
						1-23	Cl	SO 2Et	H	2	A-5
1-24	Cl	SO 2Et	H	2	A-10
						1-25	Cl	CF 3	H	2	A-3
1-26	Cl	OCHF 2	H	2	A-5
						1-27	Cl	OCF 3	H	2	A-10
1-28	Cl	CHF 2	H	2	A-3
						1-29	Br	SO 2Me	H	2	A-3
1-30	Br	SO 2Me	H	2	A-5
						1-31	Br	SO 2Me	H	2	A-10
1-32	Br	SO 2Me	H	2	A-11
						1-33	Br	SO 2Me	H	2	A-13
1-34	Br	SO 2Me	H	2	A-14
						1-35	Cl	NO 2	H	2	A-3
1-36	Cl	NO 2	H	2	A-5
						1-37	Cl	NO 2	H	2	A-10
1-38	Cl	NO 2	H	2	A-11
						1-39	Cl	SO 2Me	H	2	CH(OCH 2CH 3) 2
1-40	Cl	SO 2Me	H	3	CH(OCH 2CH 3) 2

Table 1 is continuous

Compound N o.	R 1	R 2	Q	y	A
						1-41	Cl	SO 2Me	C(＝O)Me	1	A-4
1-42	Cl	SO 2Me	C(＝O)Et	1	A-6
						1-43	Cl	SO 2Me	C(＝O)CH 2Ph	1	A-10
1-44	Cl	SO 2Me	C(＝O)Ph	1	A-12
						1-45	Cl	NO 2	C(＝O)(2-Me-Ph)	1	A-1
1-46	Cl	NO 2	C(＝O)(4-Me-Ph)	1	A-2
						1-47	Cl	NO 2	C(＝O)(4-Cl-Ph)	1	A-7
1-48	Cl	SO 2Me	C(＝O)Ph	2	A-3
						1-49	Cl	SO 2Me	C(＝S)OMe	2	A-4
1-50	Cl	SO 2Me	SO 2Ph	2	A-5
						1-51	Cl	SO 2Me	C(＝O)SMe	2	A-6
1-52	Cl	SO 2Me	SO 2Me	2	A-3
						1-53	Cl	SO 2Me	C(＝O)SPr	2	A-8
1-54	Cl	SO 2Me	C(＝O)S-iso-Pr	2	A-9
						1-55	Cl	SO 2Me	C(＝O)SPh	2	A-10
1-56	Cl	SO 2Me	C(＝O)Me	2	A-11
						1-57	Cl	SO 2Me	C(＝O)Et	2	A-12
1-58	Cl	SO 2Me	C(＝O)CH 2Ph	2	A-13
						1-59	Cl	SO 2Me	C(＝O)Ph	2	A-14
1-60	Cl	SO 2Me	C(＝O)(2-Me-Ph)	2	A-15
						1-61	Cl	SO 2Me	C(＝O)(4-Cl-Ph)	2	A-16
1-62	Cl	SO 2Et	C(＝O)NMe 2	2	A-3
						1-63	Cl	SO 2Et	C(＝O)Ph	2	A-5
1-64	Cl	SO 2Et	C(＝S)OMe	2	A-5
						1-65	Cl	CF 3	C(＝S)OPh	2	A-3
1-66	Cl	OCHF 2	C(＝O)SMe	2	A-5
						1-67	Cl	OCF 3	C(＝O)SEt	2	A-10
1-68	Cl	CHF 2	C(＝O)SPr	2	A-3
						1-69	Br	SO 2Me	SO 2NEt 2	2	A-3
1-70	Br	SO 2Me	C(＝O)SPh	2	A-5
						1-71	Br	SO 2Me	C(＝O)(2-Me-Ph)	2	A-10
1-72	Br	SO 2Me	C(＝O)(4-Me-Ph)	2	A-11
						1-73	Br	SO 2Me	C(＝O)(4-Cl-Ph)	2	A-13
1-74	Br	SO 2Me	C(＝O)Ph	2	A-14
						1-75	Cl	NO 2	C(＝O)OMe	2	A-3
1-76	Cl	NO 2	C(＝O)OPh	2	A-5
						1-77	Cl	SO 2Me	C(＝O)SMe	2	CH(OCH 2CH 3) 2
1-78	Cl	SO 2Me	C(＝O)SMe	3	CH(OCH 2CH 3) 2

Table 2

Compound N o.	R 1	R 2	Q	y	A
						2-1	Cl	SO 2Me	H	1	A-4
2-2	Cl	SO 2Me	H	1	A-6
						2-3	Cl	SO 2Me	H	1	A-10
2-4	Cl	SO 2Me	H	1	A-12
						2-5	Cl	NO 2	H	1	A-1
2-6	Cl	NO 2	H	1	A-2
						2-7	Cl	NO 2	H	1	A-7
2-8	Cl	SO 2Me	H	2	A-3
						2-9	Cl	SO 2Me	H	2	A-4
2-10	Cl	SO 2Me	H	2	A-5
						2-11	Cl	SO 2Me	H	2	A-6
2-12	Cl	SO 2Me	H	2	A-7
						2-13	Cl	SO 2Me	H	2	A-8
2-14	Cl	SO 2Me	H	2	A-9
						2-15	Cl	SO 2Me	H	2	A-10
2-16	Cl	SO 2Me	H	2	A-11
						2-17	Cl	SO 2Me	H	2	A-12
2-18	Cl	SO 2Me	H	2	A-13
						2-19	Cl	SO 2Me	H	2	A-14
2-20	Cl	SO 2Me	H	2	A-15
						2-21	Cl	SO 2Me	H	2	A-16
2-22	Cl	SO 2Et	H	2	A-3
						2-23	Cl	SO 2Et	H	2	A-5
2-24	Cl	SO 2Et	H	2	A-10
						2-25	Cl	SO 2Et	H	2	A-11
2-26	Cl	SO 2Et	H	2	A-13
						2-27	Cl	SO 2Et	H	2	A-14
2-28	Br	SO 2Me	H	2	A-3
						2-29	Br	SO 2Me	H	2	A-5
2-30	Br	SO 2Me	H	2	CH(OCH 2CH 3) 2
						2-31	Br	SO 2Me	H	3	CH(OCH 2CH 3) 2
2-32	Br	SO 2Me	H	2	A-13
						2-33	Br	SO 2Me	H	2	A-14
2-34	Cl	NO 2	H	2	A-3
						2-35	Cl	NO 2	H	2	A-5
2-36	Cl	NO 2	H	2	A-10
						2-37	Cl	NO 2	H	2	A-11

Table 2 is continuous

Compound N o.	R 1	R 2	Q	y	A
						2-38	Cl	SO 2Me	C(＝O)Me	1	A-4
2-39	Cl	SO 2Me	C(＝O)Et	1	A-6
						2-40	Cl	SO 2Me	C(＝O)CH 2Ph	1	A-10
2-41	Cl	SO 2Me	C(＝O)Ph	1	A-12
						2-42	Cl	NO 2	C(＝O)(2-Me-Ph)	1	A-1
2-43	Cl	NO 2	C(＝O)(4-Me-Ph)	1	A-2
						2-44	Cl	NO 2	C(＝O)(4-Cl-Ph)	1	A-7
2-45	Cl	SO 2Me	C(＝O)Ph	2	A-3
						2-46	Cl	SO 2Me	C(＝S)OMe	2	A-4
2-47	Cl	SO 2Me	SO 2Ph	2	A-5
						2-48	Cl	SO 2Me	C(＝O)SMe	2	A-6
2-49	Cl	SO 2Me	SO 2Me	2	A-7
						2-50	Cl	SO 2Me	C(＝O)SPr	2	A-8
2-51	Cl	SO 2Me	C(＝O)S-iso-Pr	2	A-9
						2-52	Cl	SO 2Me	C(＝O)SPh	2	A-10
2-53	Cl	SO 2Me	C(＝O)Me	2	A-11
						2-54	Cl	SO 2Me	C(＝O)Et	2	A-12
2-55	Cl	SO 2Me	C(＝O)CH 2Ph	2	A-13
						2-56	Cl	SO 2Me	C(＝O)Ph	2	A-14
2-57	Cl	SO 2Me	C(＝O)(2-Me-Ph)	2	A-15
						2-58	Cl	SO 2Me	C(＝O)(4-Cl-Ph)	2	A-16
2-59	Cl	SO 2Et	C(＝O)NMe 2	2	A-3
						2-60	Cl	SO 2Et	C(＝O)Ph	2	A-5
2-61	Cl	SO 2Et	C(＝S)OMe	2	A-10
						2-62	Cl	SO 2Et	C(＝S)OPh	2	A-11
2-63	Cl	SO 2Et	C(＝O)SMe	2	CH(OCH 2CH 3) 2
						2-64	Cl	SO 2Et	C(＝O)SMe	3	CH(OCH 2CH 3) 2
2-65	Br	SO 2Me	C(＝O)SPr	2	A-3
						2-66	Br	SO 2Me	SO 2NEt 2	2	A-5
2-67	Br	SO 2Me	C(＝O)SPh	2	A-10
						2-68	Br	SO 2Me	C(＝O)(2-Me-Ph)	2	A-11
2-69	Br	SO 2Me	C(＝O)(4-Me-Ph)	2	A-13
						2-70	Br	SO 2Me	C(＝O)(4-Cl-Ph)	2	A-14
2-71	Cl	NO 2	C(＝O)Ph	2	A-3
						2-72	Cl	NO 2	C(＝O)OMe	2	A-5
2-73	Cl	NO 2	C(＝O)OPh	2	A-10
						2-74	Cl	NO 2	C(＝O)SMe	2	A-11

Table 3

Compound N o.	R 1	R 2	Q	y	A
						3-1	Cl	SO 2Me	H	1	A-4
3-2	Cl	SO 2Me	H	1	A-6
						3-3	Cl	SO 2Me	H	1	A-10
3-4	Cl	SO 2Me	H	1	A-12
						3-5	Cl	NO 2	H	1	A-1
3-6	Cl	NO 2	H	1	A-2
						3-7	Cl	NO 2	H	1	A-7
3-8	Cl	SO 2Me	H	2	A-3
						3-9	Cl	SO 2Me	H	2	A-4
3-10	Cl	SO 2Me	H	2	A-5
						3-11	Cl	SO 2Me	H	2	A-6
3-12	Cl	SO 2Me	H	2	A-7
						3-13	Cl	SO 2Me	H	2	A-8
3-14	Cl	SO 2Me	H	2	A-9
						3-15	Cl	SO 2Me	H	2	A-10
3-16	Cl	SO 2Me	H	2	A-11
						3-17	Cl	SO 2Me	H	2	A-12
3-18	Cl	SO 2Me	H	2	A-13
						3-19	Cl	SO 2Me	H	2	CH(OCH 2CH 3) 2
3-20	Cl	SO 2Me	H	3	CH(OCH 2CH 3) 2
						3-21	Cl	SO 2Me	H	2	A-16
3-22	Br	SO 2Me	H	2	A-3
						3-23	Br	SO 2Me	H	2	A-5
3-24	Br	SO 2Me	H	2	A-10
						3-25	Br	SO 2Me	H	2	A-11
3-26	Cl	SO 2Et	H	2	A-3
						3-27	Cl	SO 2Et	H	2	A-5
3-28	Cl	SO 2Et	H	2	A-10
						3-29	Cl	SO 2Et	H	2	A-11
3-30	Cl	SO 2Et	H	2	A-15

Table 3 is continuous

Compound N o.	R 1	R 2	Q	y	A
						3-31	Cl	SO 2Me	C(＝O)Me	1	A-4
3-32	Cl	SO 2Me	C(＝O)Et	1	A-6
						3-33	Cl	SO 2Me	C(＝O)CH 2Ph	1	A-10
3-34	Cl	SO 2Me	C(＝O)Ph	1	A-12
						3-35	Cl	NO 2	C(＝O)(2-Me-Ph)	1	A-1
3-36	Cl	NO 2	C(＝O)(4-Me-Ph)	1	A-2
						3-37	Cl	NO 2	C(＝O)(4-Cl-Ph)	1	A-7
3-38	Cl	SO 2Me	C(＝O)Ph	2	A-3
						3-39	Cl	SO 2Me	C(＝S)OMe	2	A-4
3-40	Cl	SO 2Me	SO 2Ph	2	A-5
						3-41	Cl	SO 2Me	C(＝O)SMe	2	A-6
3-42	Cl	SO 2Me	SO 2Me	2	A-7
						3-43	Cl	SO 2Me	C(＝O)SPr	2	A-8
3-44	Cl	SO 2Me	C(＝O)S-iso-Pr	2	A-9
						3-45	Cl	SO 2Me	C(＝O)SPh	2	A-10
3-46	Cl	SO 2Me	C(＝O)Me	2	CH(OCH 2CH 3) 2
						3-47	Cl	SO 2Me	C(＝O)Me	3	CH(OCH 2CH 3) 2
3-48	Cl	SO 2Me	C(＝O)CH 2Ph	2	A-13
						3-49	Cl	SO 2Me	C(＝O)Ph	2	A-14
3-50	Cl	SO 2Me	C(＝O)(2-Me-Ph)	2	A-15
						3-51	Cl	SO 2Me	C(＝O)(4-Cl-Ph)	2	A-16
3-52	Br	SO 2Me	C(＝O)NMe 2	2	A-3
						3-53	Br	SO 2Me	C(＝O)Ph	2	A-5
3-54	Br	SO 2Me	C(＝S)OMe	2	A-10
						3-55	Br	SO 2Me	C(＝S)OPh	2	A-11
3-56	Cl	SO 2Et	C(＝O)SMe	2	A-3
						3-57	Cl	SO 2Et	C(＝O)SEt	2	A-5
3-58	Cl	SO 2Et	C(＝O)SPr	2	A-10
						3-59	Cl	SO 2Et	SO 2NEt 2	2	A-11
3-60	Cl	SO 2Et	C(＝O)SPh	2	A-15

Table 4

Compound N o.	R 1	R 2	Q	y	A
						4-1	Cl	NO 2	H	2	A-3
4-2	Cl	CN	H	2	A-3
						4-3	Cl	CF 3	H	2	A-3
4-4	Cl	SMe	H	2	A-3
						4-5	Cl	SOMe	H	2	A-3
4-6	Cl	SO 2Me	H	2	A-3
						4-7	Cl	SO 2NMe 2	H	2	A-3
4-8	Cl	NO 2	H	2	A-5
						4-9	Cl	CN	H	2	A-5
4-10	Cl	CF 3	H	2	A-5
						4-11	Cl	SMe	H	2	A-5
4-12	Cl	SOMe	H	2	A-5
						4-13	Cl	SO 2Me	H	2	A-5
4-14	Cl	SO 2NMe 2	H	2	A-5
						4-15	Cl	NO 2	H	2	A-10
4-16	Cl	CN	H	2	A-10
						4-17	Cl	CF 3	H	2	A-10
4-18	Cl	SMe	H	2	A-10
						4-19	Cl	SOMe	H	2	A-10
4-20	Cl	SO 2Me	H	2	A-10
						4-21	Cl	SO 2NMe 2	H	2	A-10
4-22	Cl	NO 2	H	2	A-11
						4-23	Cl	CN	H	2	A-11
4-24	Cl	CF 3	H	2	A-11
						4-25	Cl	SMe	H	2	A-11
4-26	Cl	SO 2Me	H	2	CH(OCH 2CH 3) 2
						4-27	Cl	SO 2Me	H	3	CH(OCH 2CH 3) 2
4-28	Cl	SO 2NMe 2	H	2	A-11
						4-29	Cl	NO 2	H	2	A-15
4-30	Cl	SO 2Me	H	2	A-15

Table 4 is continuous

Compound N o.	R 1	R 2	Q	y	A
						4-31	Cl	NO 2	C(＝O)Me	2	A-3
4-32	Cl	CN	C(＝O)NMe 2	2	A-3
						4-33	Cl	CF 3	C(＝O)CH 2Ph	2	A-3
4-34	Cl	SMe	C(＝O)Ph	2	A-3
						4-35	Cl	SOMe	C(＝O)(2-Me-Ph)	2	A-3
4-36	Cl	SO 2Me	C(＝O)(4-Me-Ph)	2	A-3
						4-37	Cl	SO 2NMe 2	C(＝O)(4-Cl-Ph)	2	A-3
4-38	Cl	NO 2	C(＝O)Ph	2	A-5
						4-39	Cl	CN	C(＝S)OMe	2	A-5
4-40	Cl	CF 3	SO 2Ph	2	A-5
						4-41	Cl	SMe	C(＝O)SMe	2	A-5
4-42	Cl	SOMe	SO 2Me	2	A-5
						4-43	Cl	SO 2Me	C(＝O)SPr	2	A-5
4-44	Cl	SO 2NMe 2	C(＝O)S-iso-Pr	2	A-5
						4-45	Cl	NO 2	C(＝O)SPh	2	A-10
4-46	Cl	CN	C(＝O)Me	2	A-10
						4-47	Cl	CF 3	C(＝O)Et	2	A-10
4-48	Cl	SMe	C(＝O)CH 2Ph	2	A-10
						4-49	Cl	SOMe	C(＝O)Ph	2	A-10
4-50	Cl	SO 2Me	C(＝O)(2-Me-Ph)	2	A-10
						4-51	Cl	SO 2NMe 2	C(＝O)(4-Cl-Ph)	2	A-10
4-52	Cl	NO 2	C(＝O)NMe 2	2	A-11
						4-53	Cl	CN	C(＝O)Ph	2	A-11
4-54	Cl	CF 3	C(＝S)OMe	2	A-11
						4-55	Cl	SMe	C(＝S)OPh	2	CH(OCH 2CH 3) 2
4-56	Cl	SOMe	C(＝O)SMe	3	CH(OCH 2CH 3) 2
						4-57	Cl	SO 2Me	C(＝O)SEt	2	A-11
4-58	Cl	SO 2NMe 2	C(＝O)SPr	2	A-11
						4-59	Cl	NO 2	SO 2NEt 2	2	A-15
4-60	Cl	SO 2Me	C(＝O)SPh	2	A-15

Table 5

Compound N o.	R 1	R 2	Q	y	A
						5-1	Cl	SO 2Me	H	1	A-4
5-2	Cl	SO 2Me	H	1	A-6
						5-3	Cl	SO 2Me	H	1	A-10
5-4	Cl	SO 2Me	H	1	A-12
						5-5	Cl	NO 2	H	1	A-1
5-6	Cl	NO 2	H	1	A-2
						5-7	Cl	NO 2	H	1	A-7
5-8	Cl	SO 2Me	H	2	A-3
						5-9	Cl	SO 2Me	H	2	A-4
5-10	Cl	SO 2Me	H	2	A-5
						5-11	Cl	SO 2Me	H	2	A-6
5-12	Cl	SO 2Me	H	2	A-7
						5-13	Cl	SO 2Me	H	2	A-8
5-14	Cl	SO 2Me	H	2	A-9
						5-15	Cl	SO 2Me	H	2	A-10
5-16	Cl	SO 2Me	H	2	A-11
						5-17	Cl	SO 2Me	H	2	CH(OCH 2CH 3) 2
5-l8	Cl	SO 2Me	H	3	CH(OCH 2CH 3) 2
						5-19	Cl	SO 2Me	H	2	A-14
5-20	Cl	SO 2Me	H	2	A-15
						5-21	Cl	SO 2Me	H	2	A-16
5-22	Br	SO 2Me	H	2	A-3
						5-23	Br	SO 2Me	H	2	A-5
5-24	Br	SO 2Me	H	2	A-10
						5-25	Br	SO 2Me	H	2	A-11
5-26	Cl	SO 2Et	H	2	A-3
						5-27	Cl	SO 2Et	H	2	A-5
5-28	Cl	SO 2Et	H	2	A-10
						5-29	Cl	SO 2Et	H	2	A-11
5-30	Cl	SO 2Et	H	2	A-15

Table 5 is continuous

Compound N o.	R 1	R 2	Q	y	A
						5-31	Cl	SO 2Me	C(＝O)Me	1	A-4
5-32	Cl	SO 2Me	C(＝O)Et	1	A-6
						5-33	Cl	So 2Me	C(＝O)CH 2Ph	1	A-10
5-34	Cl	SO 2Me	C(＝O)Ph	1	A-12
						5-35	Cl	NO 2	C(＝O)(2-Me-Ph)	1	A-1
5-36	Cl	NO 2	C(＝O)(4-Me-Ph)	1	A-2
						5-37	Cl	NO 2	C(＝O)(4-Cl-Ph)	1	A-7
5-38	Cl	SO 2Me	C(＝O)Ph	2	A-3
						5-39	Cl	SO 2Me	C(＝S)OMe	2	A-4
5-40	Cl	SO 2Me	SO 2Ph	2	A-5
						5-41	Cl	SO 2Me	C(＝O)SMe	2	A-6
5-42	Cl	SO 2Me	SO 2Me	2	A-7
						5-43	Cl	SO 2Me	C(＝O)SPr	2	A-8
5-44	Cl	SO 2Me	C(＝O)S-iso-Pr	2	A-9
						5-45	Cl	SO 2Me	C(＝O)SPh	2	A-10
5-46	Cl	SO 2Me	C(＝O)Me	2	A-11
						5-47	Cl	SO 2Me	C(＝O)Et	2	A-12
5-48	Cl	SO 2Me	C(＝O)CH 2Ph	2	A-13
						5-49	Cl	SO 2Me	C(＝O)Ph	2	A-14
5-50	Cl	SO 2Me	C(＝O)(2-Me-Ph)	2	A-15
						5-51	Cl	SO 2Me	C(＝O)(4-Cl-Ph)	2	A-16
5-52	Br	SO 2Me	C(＝O)NMe 2	2	A-3
						5-53	Br	SO 2Me	C(＝O)Ph	2	A-5
5-54	Br	SO 2Me	C(＝S)OMe	2	A-10
						5-55	Br	SO 2Me	C(＝S)OPh	2	A-11
5-56	Cl	SO 2Et	C(＝O)SMe	2	A-3
						5-57	Cl	SO 2Et	C(＝O)SEt	2	A-5
5-58	Cl	SO 2Et	C(＝O)SPr	2	A-10
						5-59	Cl	SO 2Et	SO 2NEt 2	2	A-11
5-60	Cl	SO 2Et	C(＝O)SPh	2	A-15

Table 6

Compound N o.	Fusing point
		1-1	115-118℃
1-9	125-127℃

Table 7

Compound N o.	1H-NMR(CDCl 3.300MHz)：6(ppm)
		1-3	1.54-1.58(m，1H)，1.91-2.0(m，1H)，2.09(t，2H)，2.45(t，2H)， 2.82(t，2H)，3.32(s，3H)，3.81(dt，1H)，4.15-4.45(m，3H)， 4.80(d，1H)，5.16(d，1H)，7.10(d，1H)，7.95(d，1H)
1-4	1.36(d，3H)，1.52-1.49(m，1H)，1.80-1.92(m，1H)，2.07(t，2H)， 2.44(t，2H)，2.81(t，2H)，3.13(s，3H)，3.83(dt，1H)， 4.19-4.14(m，3H)，4.40(q，1H)，4.79(q，1H)，7.08(d，1H)，7.94(d，1H)
		1-8	2.0(t，2H)，2.18-2.24(m，2H)，2.38(t，2H)，2.74(t，2H)， 3.22(s，3H)，3.80-3.83(m，2H)，3.91-3.94(m，2H)， 4.32(t，2H)，5.08(t，1H)，6.99(d，1H)，7.85(d，1H)
1-10	1.26-1.30(m，3H)，2.07(t，2H)，2.24-2.29(m，2H)，2.44(t，2H)， 2.81(t，2H)，3.29(s，3H)，3.40-3.47(m，1H)，3.96(t，1H)， 4.15-4.17(m，1H)，4.27-4.40(m，2H)，5.18(t，1H)，7.06(d，1H)， 7.92(d，1H)
		1-15	1.57-1.62(m，1H)，1.83-1.89(m，1H)，2.03-2.14(m，4H)， 2.45(t，2H)，2.82(t，2H)，3.25(s，3H)，3.74(dt，1H)， 3.89-3.93(m，1H)，4.10-4.15(m，1H)，4.33-4.39(m，2H)， 4.72(d，1H)，5.05(d，1H)，7.06(d，1H)，7.92(d，1H)
1-16	1.33-1.38(m，1H)，2.05-2.22(m，5H)，2.45(t，2H)，2.82(t，2H)， 3.27(s，3H)，3.79(dt，2H)，4.09-4.14(m，2H)，4.35(t，2H)， 4.85(t，1H)，7.05(d，1H)，792(d，1H)
		1-18	1.24(d，6H)，1.53-1.60(m，2H)，2.07(t，2H)，2.24(q，2H)， 2.48(t，2H)，2.80(t，2H)，3.26(s，3H)，3.75(m，2H)， 4.39(t，2H)，4.89(t，1H)，7.05(d，1H)，7.90(d，1H)
1-19	0.72(s，3H)，1.20(s，3H)，2.05(t，2H)，2.22(q，2H)，2.44(t，2H)， 2.80(t，2H)，3.28(s，3H)，3.46(d，2H)，3.63(d，2H)，4.38(t，2H)， 4.76(t，1H)，7.08(d，1H)，7.94(d，1H)
		1-39	1.24(t，6H)，2.08(t，2H)，2.22(q，2H)，2.45(t，2H)，2.82(t，2H)， 3.26(s，3H)，3.56(q，2H)，3.71(q，4H)，4.33(t，2H)，4.83(t，1H)， 7.06(d，1H)，7.93(d，1H)
1-48	2.05(t，2H)，2.20-2.26(m，2H)，2.45(t，2H)，2.80(t，2H)， 3.25(s，3H)，3.82-3.85(m，2H)，3.93-3.96(m，2H)，4.32(t，2H)， 5.08(t，1H)，7.37-7.65(m，6H)，7.85(d，1H)

Below, put down in writing test example of the present invention

The test example

1/1,000, behind the paddy field soil of packing in 000 hectare of jar, sow the seed of wild barnyard grass and Fischer grass, thereon overburden soil lightly.Thereafter the state with the dark 0.5～1cm of retaining is statically placed in the greenhouse, implants the stem tuber of arrowhead after second day or 2 days.Keep the dark 3～4cm of retaining thereafter, barnyard grass out of office and Fischer grass reach the time point that 0.5 leaf phase, arrowhead reach the primary leaf phase, the wettable powder that will form according to common formulation method modulation The compounds of this invention or the water diluent of emulsion drip processing to reach regulation effective constituent amount equably with pipette.

In addition, 1/1,000, pack in 000 hectare of jar behind the paddy field soil, carry out paddy-field flattening, make the dark 3～4cm of retaining, second day to transplant the rice (kind: Japan is fine) that dark 3cm transplanted for 2 leaf phases.Transplanted the back the 4th day and the above-mentioned The compounds of this invention of similarly handling.

The fertility status of the 21st day rice after the fertility status of the 14th day wild barnyard grass, Fischer grass and arrowhead, the chemicals treatment after the chemicals treatment that detects by an unaided eye respectively, press down careless (%) with 0 (district is equal to non-processor)～100 (withered fully killing) estimates herbicidal effect, thereby obtained the result of table 8.

Table 8

Compound N o.	Effective constituent amount (g/ha)	Press down careless (%)
						Wild barnyard grass	The Fischer grass	Arrowhead	Rice
		1-8	125 63	100 100	98 95					95 95	20 0
1-9	125 63					100 100	95 80	95 95	20 20
		1-10	125 63	90 70	98 95					98 95	10 0
1-15	125 63					100 90	95 90	95 95	10 10
		1-16	125 63	95 70	95 70					98 90	40 50
1-4	125 63					100 100	98 95	100 98	0 0
		1-18	125 63	0 0	100 60					95 95	- 10
1-19	125 63					10 0	95 95	95 95	10 0
		1-39	125 63	98 30	80 60					95 90	20 10
1-48	125 63					70 0	95 80	95 90	20 0

Below, put down in writing formulation example of the present invention.

Formulation example 1

(1) The compounds of this invention 75 weight parts

(2) ゲ ロ Port Application T-77 (trade(brand)name; ロ one ヌ プ one ラ Application society system) 14.5 weight parts

(3) NaCl 10 weight parts

(4) dextrin 0.5 weight part

Above each composition is packed in the high-speed mixing fine-graining machine, and then after the water that wherein adds 20% carries out granulation, drying, obtain the particle wettable powder.

Formulation example 2

(1) kaolin 78 weight parts

(2) ラ ベ リ Application FAN (trade(brand)name; The first industrial pharmacy (strain) system) 2 weight parts

(3) ソ Le Port one Le 5039 (trade(brand)names; East nation's chemical industry (strain) system) 5 weight parts

(4) カ one プ レ Star Network ス (trade(brand)name; Shionogi (strain) system) 15 weight parts

The mixture of ingredients of above (1)～(4) and the The compounds of this invention part by weight with 9: 1 is mixed, obtain wettable powder.

Formulation example 3

(1) Ha イ Off イ ラ one No.10 (trade(brand)name; Pine village's industry (strain) system) 33 weight parts

(2) ソ Le Port one Le 5050 (trade(brand)names; East nation's chemical industry (strain) system) 3 weight parts

(3) ソ Le Port one Le 5073 (trade(brand)names; East nation's chemical industry (strain) system) 4 weight parts

(4) The compounds of this invention 60 weight parts

Each composition that mixes above (1)～(4) obtains wettable powder.

Formulation example 4

(1) The compounds of this invention 4 weight parts

(2) bentonite 30 weight parts

(3) salt of wormwood 61.5 weight parts

(4) ト キ サ ノ Application GR-31A (trade(brand)name; Sanyo changes into industry (strain) system) 3 weight parts

(5) calcium lignin sulphonate 1.5 weight parts

Mix (1), (2) and (3) of pulverizing in advance, after wherein adding (4), (5) and water mix, extruding pelletization.Thereafter, thus dry, granulation obtains granule.

Formulation example 5

(1) The compounds of this invention 30 weight parts

(2) ジ one Network ラ イ ト (trade(brand)name; ジ one Network ラ イ ト (strain) system) 60 weight parts

(3) ニ ユ one カ Le ゲ Application WG-1 (trade(brand)name; This grease of bamboo (strain) system) 5 weight parts

(4) ニ ユ one カ Le ゲ Application FS-7 (trade(brand)name; This grease of bamboo (strain) system 5 weight parts

Mix (1), (2) and (3), behind pulverizer, adding (4) is mixing, carries out extruding pelletization again.Thereafter, thus dry, granulation obtains the particle wettable powder.

Formulation example 6

(1) The compounds of this invention 28 weight parts

(2) ソ Port ロ Port one Le FL (trade(brand)name; ロ one ヌ プ one ラ Application society system) 2 weight parts

(3) ソ Le Port one Le 355 (trade(brand)names; East nation's chemical industry (strain) system) 1 weight part

(4) IP ソ Le ベ Application ト 1620 (trade(brand)names; Bright dipping petroleum chemistry (strain) system) 32 weight parts

(5) ethylene glycol 6 weight parts

(6) water 31 weight parts

Mix above (1)～(6), after use wet crushing mill (ダ イ ノ one ミ Le) is pulverized, obtain the aqueous suspension agent.

Utilizability on the industry

The invention provides as the useful new trione compounds of the active ingredient of herbicide, its manufacture method and contain the herbicide of this compounds.

In addition, quote the full content of Japanese patent application 2004-165472 number specification sheets, claims, accompanying drawing and the summary of filing an application on June 3rd, 2004, as the open content of being introduced of specification sheets of the present invention at this.

Claims (8)

1. the trione compounds shown in the formula (I) or its salt,

[changing 1]

In the formula, y is 1～6 integer; A contains 1～2 at least a kind of heteroatomic 5 or 6 yuan of saturated heterocyclyl (heterocyclic radical can be replaced by alkyl) or dialkoxy methyl that is selected from the group that Sauerstoffatom and sulphur atom form; R ¹Be halogen; R ²Be alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, alkylthio, halogenated alkylthio, alkyl sulphinyl, haloalkyl sulfinyl, alkyl sulphonyl, halogenated alkyl sulfonyl, dialkyl amino sulfonyl, two (haloalkyl) amino-sulfonyl, nitro or cyano group; R ³, R ⁴, R ⁶, R ⁷And R ⁸Be respectively hydrogen atom or alkyl; R ⁵Be hydrogen atom, alkyl or cycloalkyl, R ⁵And R ⁸Can form 3～6 yuan of saturated carbon rings together, R ⁵And R ⁶Can form ketone together; Q be hydrogen atom ,-C (=O)-(CH ₂) _n-R ⁹,-C (=L)-M-R ⁹,-C (=L)-N (R ⁹) R ¹⁰,-SO ₂-N (R ⁹) R ¹⁰, or-SO ₂-R ⁹L and M are respectively Sauerstoffatom or sulphur atom; N is 0～3; R ⁹And R ¹⁰Be respectively hydrogen atom, alkyl, alkoxyalkyl, alkoxyl group, can substituted phenyl or can substituted benzyl; R ⁹And R ¹⁰Can form 5 or 6 yuan of saturated heterocyclyls together; But y is 1, and A is 1, and 3-two  alkane-2-base or 1 is except the occasion of 3-two oxa-s penta ring-2-base.

2. compound or its salt as claimed in claim 1, wherein y is 1～6 integer; A contains 1～2 at least a kind of heteroatomic 5 or 6 yuan of saturated heterocyclyl (heterocyclic radical can be replaced by alkyl) that are selected from the group that Sauerstoffatom and sulphur atom form; R ¹Be halogen; R ²Be alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, alkylthio, halogenated alkylthio, alkyl sulphinyl, haloalkyl sulfinyl, alkyl sulphonyl, halogenated alkyl sulfonyl, dialkyl amino sulfonyl, two (haloalkyl) amino-sulfonyl, nitro or cyano group; R ³, R ⁴, R ⁶, R ⁷And R ⁸Be respectively hydrogen atom or alkyl; R ⁵Be hydrogen atom, alkyl or cycloalkyl, R ⁵And R ⁸Can form 3～6 yuan of saturated carbon rings together, R ⁵And R ⁶Can form ketone together; Q is a hydrogen atom; But y is 1, and A is 1, and 3-two  alkane-2-base or 1 is except the occasion of 3-two oxa-s penta ring-2-base.

3. compound or its salt as claimed in claim 1 or 2, wherein R ²Be haloalkyl, halogenated alkoxy, alkylthio, alkyl sulphinyl, alkyl sulphonyl, dialkyl amino sulfonyl, nitro or cyano group.

4. as wantonly 1 described compound or its salt of claim 1～3, wherein y is 2.

5. as wantonly 1 described compound or its salt of claim 1～3, wherein y is 2; R ³, R ⁴, R ⁵, R ⁶, R ⁷And R ⁸Be respectively hydrogen atom.

6. the trione compounds of formula (I) expression or the manufacture method of its salt is characterized in that, (1) makes the compound and the R of formula (I-1) expression ¹¹-C (=O)-Hal, R ¹²-C (=S)-Hal, R ¹³-SO ₂The reaction of compound that-Hal represents, or (2) reset the compound of formula (II) expression, or the compound of (3) oxidation-type (I-1-1) expression,

Formula (I):

In the formula, y is 1～6 integer; A contains 1～2 at least a kind of heteroatomic 5 or 6 yuan of saturated heterocyclyl (heterocyclic radical can be replaced by alkyl) or dialkoxy methyl that is selected from the group that Sauerstoffatom and sulphur atom form; R ¹Be halogen; R ²Be alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, alkylthio, halogenated alkylthio, alkyl sulphinyl, haloalkyl sulfinyl, alkyl sulphonyl, halogenated alkyl sulfonyl, dialkyl amino sulfonyl, two (haloalkyl) amino-sulfonyl, nitro or cyano group; R ³, R ⁴, R ⁶, R ⁷And R ⁸Be respectively hydrogen atom or alkyl; R ⁵Be hydrogen atom, alkyl, cycloalkyl, R ⁵And R ⁸Can form 3～6 yuan of saturated carbon rings together, R ⁵And R ⁶Can form ketone together; Q be hydrogen atom ,-C (=O)-(CH ₂) _n-R ⁹,-C (=L)-M-R ⁹,-C (=L)-N (R ⁹) R ¹⁰,-SO ₂-N (R ⁹) R ¹⁰, or-SO ₂-R ⁹L and M are respectively Sauerstoffatom or sulphur atom; N is 0～3; R ⁹And R ¹⁰Be respectively hydrogen atom, alkyl, alkoxyalkyl, alkoxyl group, can substituted phenyl or can substituted benzyl; R ⁹And R ¹⁰Can form 5 or 6 yuan of saturated heterocyclyls together; But y is 1, and A is 1,3-two  alkane-2-base or 1, and except the occasion of 3-two oxa-s penta ring-2-base,

Formula (I-1):

In the formula, y, A, R ¹, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷And R ⁸As previously described,

R ¹¹-C (=O)-Hal, R ¹²-C (=S)-Hal, R ¹³-SO ₂The compound that-Hal is represented:

In the formula, Hal is a halogen, R ¹¹For-(CH ₂) _n-R ⁹,-M-R ⁹, or-N (R ⁹) R ¹⁰, R ¹²For-M-R ⁹Or-N (R ⁹) R ¹⁰, R ¹³Be R ⁹Or-N (R ⁹) R ¹⁰, R ⁹, R ¹⁰, M and n as previously described,

Formula (II):

In the formula, y, A, R ¹, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷And R ⁸As previously described,

Formula (I-1-1):

In the formula, y, A, R ¹, R ³, R ⁴, R ⁵, R ⁶, R ⁷And R ⁸As previously described, R ¹⁴Be alkyl or haloalkyl.

7. weedicide, it contains the described trione compounds of claim 1～5 or its salt as effective constituent.

8. the method for control of a noxious plant is used the described trione compounds of claim 1～5 or its salt of herbicidally effective amount.