WO2000024250A1 - Cyclobutenedione derivatives having nematicidal activities - Google Patents

Abstract

Nematicides effective in exterminating various nematodes, which contain compounds represented by general formula (I), salts of the same, or hydrates of both wherein G?1 and G2¿ are each independently aliphatic hydrocarbyl which may be substituted with a specific group, a group represented by the general formula: O-R1 (wherein R1 is hydrogen, optionally substituted aliphatic hydrocarbyl, or the like), or the like.

Description

 Description Cyclobutenedione derivative having nematicidal activity

 TECHNICAL FIELD The present invention relates to a nematicide, which is a kind of agricultural or veterinary drug, particularly a cyclobutenedione derivative having nematicidal activity. Background art

 As nematicides, D-D (1,3-dichlorobronone), chloropicrin, oxamil, bromide, and methyl bromide are used for nematode control in soil and fumigants. .

 As a butenedione derivative similar to the compound contained in the nematocide of the present invention, a compound having a herbicidal activity described in JP-A-51-15030 is known. Disclosure of the invention

 An object of the present invention is to provide a novel nematocide that is safe and low in toxicity.

 As a result of various studies, the present inventors have found that certain cyclobutene derivatives have nematicidal activity, and have completed the present invention.

 The present invention

 (1) General formula (I):

(R

Wherein G ¹ and G are each independently a halogen, a hydroxyl group, a lower alcohol Xyl group, halogenated lower alkoxy group, lower alkenyloxy group, halogenated lower alkenyloxy group, carboxyl, lower alkoxycarbonyl group, mercapto, lower alkylthio group, aromatic hydrocarbon group or heterocyclic group ( The aromatic hydrocarbon group and the heterocyclic group include a halogen, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a halogenated lower alkenyl group, a lower alkoxy group, a lower alkenyloxy group, Which may have 1 to 5 anonymous groups selected from the group consisting of halogenated lower alkoxy groups, halogenated lower alkenyloxy groups, mercapto and lower alkylthio groups) An aromatic hydrocarbon group, an optionally substituted lower alkoxycarbonyl group, or Formula: A 0- R ¹ or the formula: - S- group (wherein represented by R ^1, R ¹ is a hydrogen atom, its been it optionally substituted aliphatic hydrocarbon group, Amino, alicyclic A hydrocarbon group, an aromatic hydrocarbon group, or a heterocyclic group, or a group represented by the formula: C ¹ — A ¹ (where A ¹ is an optionally substituted aliphatic hydrocarbon group or aromatic hydrocarbon group, or a group of the formula: a group represented by one 0- Q ¹ (in formula ^(I), Q ¹ represents a hydrogen atom or an aliphatic substituted hydrocarbon group))) ], A nematicide containing a compound thereof, a salt thereof or a hydrate thereof,

(2) The substituents of the aliphatic hydrocarbon group represented by R ¹ A ¹ and Q ¹ are each independently a halogen, a hydroxyl group, a lower alkoxy group, a halogenated lower alkoxy group, a lower alkenyloxy group. , Halogenated lower alkenyloxy, lower alkynyloxy, optionally substituted phenyl lower alkyloxy, optionally substituted phenyloxy, mercapto, lower alkylthio, amino, mono-lower alkylamino, di-lower alkyl Amino group, carboxyl, lower alkoxycarbonyl group, halogenated lower alkoxycarbonyl group, lower alkenyloxycarbonyl group, halogenated lower alkenyloxycarbonyl group, lower alkoxy dioxycarbonyl group, optionally substituted phenylo Xycarbonyl, substituted Aromatic hydrocarbon group, optionally substituted heterocyclic group, lower alkanoyloxy group, optionally substituted rubamoyl, cyano, substituted A nematicide according to (1), which is an optionally substituted sulfonyl, optionally substituted silyl, sulfo, optionally substituted alicyclic hydrocarbon group or phosphoric acid residue, (3) R ¹ , A ¹ and Q ¹ each independently represent a halogen, a hydroxyl group, a lower alkoxy group, a halogenated lower alkoxy group, a lower alkenyloxy group, a halogenated lower alkenyloxy group. Group, mercapto, lower alkylthio group, amino, mono-lower alkylamino group, di-lower alkylamino group, carboxyl, lower alkoxycarbonyl group, aromatic hydrocarbon group or heterocyclic group (the aromatic hydrocarbon group and The heterocyclic group includes a halogen, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a halogenated lower alkyl group. Has 1 to 5 substituents selected from the group consisting of a benzyl group, a lower alkoxy group, a lower alkenyloxy group, a halogenated lower alkoxy group, a halogenated lower alkenyloxy group, mercapto and a lower alkylthio group. The nematicide described in (1) or (2),

(4) G ¹ and G ² are each independently of the formula: A 0- R ¹ or the formula: - group (wherein represented by S- R ^1, R ¹ is halogen, hydroxyl, a lower alkoxy group , A halogenated lower alkoxy group, a lower alkenyloxy group, a halogenated lower alkenyloxy group, a mercapto, a lower alkylthio group, an amino, a mono-lower alkylamino group, a di-lower alkylamino group, a carboxyl, a lower alkoxycarbonyl group, or Is a phenyl (the phenyl is a halogen, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a halogenated lower alkenyl group, a lower alkoxy group, a lower alkenyloxy group, a halogenated lower alkoxy group, Halogenated from the group consisting of lower alkenyloxy, mercapto and lower alkylthio Represents a lower alkyl group or a lower alkenyl group optionally substituted with 1 to 5 selected substituents), or (1) to (3). Nematicide,

(5) R ¹ is a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a halogenated lower alkenyl group, a lower alkyl group substituted with a hydroxyl group, a lower alcohol A nematicide according to any one of (1) to (4), which is a xy lower alkyl group or a phenylalkyl group which may be substituted;

(6) G ¹ and G ² power ^s, which it independently, formula: A 0- group (wherein represented by R ^1, R ¹ is a lower alkyl group or a lower alkenyl group (the lower alkyl group Contact And the lower alkenyl group may have 1 to 3 substituents selected from the group consisting of halogen, a hydroxyl group and a lower alkoxy group, or benzyl or phenethyl (the benzyl and the phenyl). Phenyl is a halogen, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a halogenated lower alkenyl group, a lower alkoxy group, a lower alkenyloxy group, a halogenated lower alkoxy group, a halogenated lower alkenyl group. Which may have from 1 to 5 substituents selected from the group consisting of an oxy group, a mercapto group and a lower alkylthio group). (1) - nematicide of any one of (5),

(7) The nematicide according to any of (1) to (6), wherein G ¹ and G ² are the same, and

(8) 0 ¹ Oyobi 0 ² are each independently of the main butoxy, ethoxy, isopropylidene Ruokishi, t one-butoxy, 1 one Echirupuropokishi, Ariruokishi, 1, 3-dimethyl Chirubutokishi or base Njiruokishi, It provides a nematicide according to any one of (1) to (7). BEST MODE FOR CARRYING OUT THE INVENTION

 The term “lower” as used herein, unless otherwise specified, refers to a group having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms.

The aliphatic hydrocarbon group of the “optionally substituted aliphatic hydrocarbon group” represented by G ¹ , G ² , R ¹ , A ¹ and Q ¹ is a straight-chain such as an alkyl group, an alkenyl group and an alkynyl group. A chain or branched aliphatic hydrocarbon group.

The alkyl group which is an “optionally substituted aliphatic hydrocarbon group” represented by G ¹ G ² , R ¹ , A ¹ and Q ¹ is preferably a linear or branched C 1 to C 2 It is an alkyl group of 0. For example, methyl, ethyl, propyl, isopropyl, n-butyl, y-butyl, s-butyl, t-pentyl, pentyl, isopentyl, neopentyl, t-pentyl, 1-ethylpropyl, hexyl, isohexyl, heptyl, octyl Decyl, tetrahydrogeranyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octyldecyl, nonadecyl, eicosanil and the like. More preferably, it is a C 1 -C 10 alkyl group. Of these, methyl, ethyl, propyl, isopropyl and n-butyl are preferred. Most preferred is methyl.

The alkenyl group which is the “optionally substituted aliphatic hydrocarbon group” shown on G ¹ , G ² , R ¹ , A ¹ and Q ¹ preferably has one or more double bonds. It is a linear or branched C2-C20 alkenyl group having the above. For example, vinyl, aryl, isopropyl, 1-propenyl, 2-methyl-1-probenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-ethyl-1 butenyl, 3-methyl-2-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 4-methyl-3-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 to 1 Butenyl, 1-octenyl, geranyl, 1-decenyl, 1-tetradecenyl, 1 year old Kutadecenyl, 9 year old Kutadecenyl, 1 eicosenyl, and 3,7,11,15-tetramethyl-11-hexadecenyl No. More preferably, it is a C2-C8 alkenyl group. Of these, vinyl, aryl and isopropyl are preferred. Most preferred is vinyl.

The alkynyl group which is the `` optionally substituted aliphatic hydrocarbon group '' represented by G ¹ , G ² , R ¹ , A ¹ and Q ¹ preferably has a C 2 to C 20 double bond. It is an alkynyl group which may be substituted. For example, ethynyl, 1-propynyl, 2-propynyl, 2-pentene-4-ynyl and the like can be mentioned. More preferably, it is a C2-C8 alkynyl group. Most preferred is ethynyl.

Substitution of “optionally substituted aliphatic hydrocarbon group” represented by G ¹ and G ² The groups are each independently a halogen, a hydroxyl group, a lower alkoxy group, a halogenated lower alkoxy group, a lower alkenyloxy group, a halogenated lower alkenyloxy group, a carboxyl, a lower alkoxycarbonyl group, a mercapto, a lower alkylthio group. Group, aromatic hydrocarbon group or heterocyclic group (the aromatic hydrocarbon group and the heterocyclic group are halogen, hydroxyl, lower alkyl, lower alkenyl, halogenated lower alkyl, halogenated lower alkenyl) A lower alkoxy group, a lower alkenyloxy group, a halogenated lower alkoxy group, a halogenated lower alkenyloxy group, a mercapto and a lower alkylthio group, each having 1 to 5 substituents. ). More preferred are halogen, hydroxyl, lower alkoxy, mercapto and lower alkylthio. The number of these substituents is one to five, preferably one to three. The substituents may be the same or different. The position of the substituent is not particularly limited.

It is a preferred correct specific example of the "optionally substituted aliphatic hydrocarbon group" represented by G ¹ and G 2, for example, methyl, Furuoromechiru, chloromethyl, bromomethyl, Jifuruoromechiru, dichloromethyl, black hole Fluoromethyl, trifluoromethyl, trichloromethyl, hydroxymethyl, mercaptomethyl, methylthiomethyl, methoxymethyl, ethyl, 2-fluoroethyl, 1 fluoroethyl, 2-chloroethyl, 1-chloroethyl, 2,2-dichloroethyl, 1 , 2—Dichloroethyl, 1,1 Dichloroethyl, 2—Chloro-1-fluoroethyl, 1-Chloro-2-fluoroethyl, 1,1 Dichloro-2,2-Difluoroethyl, 1,2—Dichloro-1,2—Dichloroethyl, 2,2— Dichro Mouth 1, 1 , 2-Hydroxitytil, 1-Hydroxitytyl, 2,2-Hydroxitytyl, 1,2-Hydroxitytyl, 1-1-Hydroxyshetyl, 1-Fluoro-2-hydroxitytyl, 2-Methoxyxetil, 2-mercaptoethyl, 2-methylthioethyl, n-propyl, 2-fluoro n-propyl, 2-clo n-propyl, 3-fluoro n-propyl, 3-clo n-propyl pill, 2, 3 —difluoro n-propyl, 2, 3 —dichloropropyl, 2, 3, 3 — Trifluoro n-propyl, 2, 3, 3 — Triclo n-propyl, Isop pill, n-butyl, t-butyl, 1-ethylpropyl, aryl, 1,3-dimethylbutyl, benzyl And methoxycarbonylmethyl.

Specific examples of the substituent of the “optionally substituted aliphatic hydrocarbon group” represented by R ¹ , A 1 and Q ¹ include, for example, halogen, hydroxyl group, lower alkoxy group, and lower alkoxy group Group, lower alkenyloxy group, halogenated lower alkenyloxy group, optionally substituted phenyloxy, mercapto, lower alkylthio group, amino, mono-lower alkylamino group, di-lower alkylamino group, carboxyl, lower alkoxycarbonyl Group, halogenated lower alkoxycarbonyl group, lower alkenyloxycarbonyl group, halogenated lower alkenyloxycarbonyl group, lower alkynyloxycarbonyl group, optionally substituted phenyloxycarbonyl, optionally substituted aromatic Group hydrocarbon group, which may be substituted A cyclic group, a lower alkanoyloxy group, an optionally substituted rubamoyl, cyano, an optionally substituted sulfonyl, an optionally substituted silyl, a sulfo, an optionally substituted alicyclic Examples include a formula hydrocarbon group and a phosphoric acid residue. More preferably, halogen, hydroxyl, lower alkoxy, halogenated lower alkoxy, lower alkenyloxy, halogenated lower alkenyloxy, mercapto, lower alkylthio, amino, mono-lower alkylamino, di A lower alkylamino group, a carboxyl, a lower alkoxycarbonyl group, an aromatic hydrocarbon group and a heterocyclic group (the aromatic hydrocarbon group and the heterocyclic group each independently represent a halogen, a hydroxyl group, a lower Group consisting of alkyl group, lower alkenyl group, halogenated lower alkyl group, halogenated lower alkenyl group, lower alkoxy group, lower alkenyloxy group, halogenated lower alkoxy group, halogenated lower alkenyloxy group, mercapto and lower alkylthio group 1 ~ 5 pieces selected from Which may have a substituent). More preferably, a halogen, a hydroxyl group, a lower alkoxy group, and a phenyl (the phenyl is a halogen, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, and a lower alkoxy group) Which may have 1 to 5 substituents selected from the group consisting of: The number of these substituents is one to five, preferably one to three. The substituents may be the same or different. The position of the substituent is not particularly limited.

Preferred specific examples of the "optionally substituted aliphatic hydrocarbon group" for R 1, A ¹ and Q ¹ include, for example, methyl, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, Fluoromethyl, trifluoromethyl, trichloromethyl, hydroxymethyl, mercaptomethyl, methylthiomethyl, methoxymethyl, ethyl, 2-fluoroethyl, 1-fluoroethyl, 2,2 difluoroethyl, 2-chloroethyl, 1-chloroethyl, 2 , 2—Dichloroethyl, 2,2,2—Trifluoroethyl, 1,1,2,2,2 —Penfufluoroethyl, 1,2—Dichloroethyl, 1,1 Dichloroethyl, 2—Chloro-1-fluoroethyl, 1-Chloroethyl 2 — Fluoroethyl, 1, 1 1 Dichloro-2, 2 — Fluoroethyl, 1, 2—Dichloro-1,2—Difluorethyl, 2,2—Dichloro-1,1, Difluoroethyl, 2—Hydroxicetil, 1—Droxoxetil, 2,2—Djilodoxetil, 1,2—Dihydrodoxetil Chill, 1 —chloro-2 —hydroxyl, 1 —fluoro-2 —hydroxyl, 2 —methoxetyl, 2 —mercaptoethyl, 2 —methylthioethyl, n—propyl, 2 —fluoron—propyl, 2 —chloro-n— Propyl, 3 —fluoro n-propyl, 3 —chloro-n-propyl, 2,3-difluoro-n-propyl, 2,3 —dichloropropyl, 2,3,3 — trifluoro n-propyl, 2,, 3,3—Trichloro mouth n-propyl, isopropyl, n-butyl, t-butyl, 1-ethylpropyl, aryl, 1,3-dimethylbutyl Cyl, fluoromethoxymethyl, difluoromethoxymethyl, tolufluoromethoxymethyl, ethoxymethyl, n-propoxymethyl, aryloxymethyl, 2,3,3—trifluoroallyloxymethyl, 2-propynyloxymethyl, isopropyloxymethyl, isobutyloxymethyl , Phenoxymethyl, carboxymethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, aryl Oxycarbonylmethyl, 2,3,3—trifluoroallyloxycarbonylmethyl, 2-propynyloxycarbonylmethyl, isopropoxycarbonylmethyl, t-butoxycarbonylmethyl, phenoxycarbonylmethyl, Aminocarbonylmethyl, N-methylaminocarbonylmethyl, N, N-dimethylaminoforce Rubonylmethyl, N-ethylaminocarbonylmethyl, N, N-Getylaminocarbonylmethyl, Nn-propylaminocarbonylmethyl, N, N— D-N-propylaminocarbonylmethyl, N-isopropylaminocarbonylmethyl, N-t-butylaminocarbonylmethyl, N-phenylaminocarbonylmethyl, N-phenylaminoN-methylaminocarbonylmethyl, 2-Fluorometoxetyl , 2—Gifolo Methoxyxetil, 2 — trifluorome methoxymethyl, 2 — trifluorome ethoxy 1 trafluroethyl, 2 — ethoxyxil, 2 — pentafluorene ethoxyethyl, 2-n-propoxyxetil, 2 — allyloxyethyl, 2 — (2,3,3—trifluoroallyloxy) -ethyl, 2- (2-provinyloxy) -ethyl, 2-isopropylisopropyl, 2- (t-butoxy) ethyl, 2-phenoxethyl, 2-benzyloxyxetyl, 2-carboxyxethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-n-proviroxycarbonylethyl, 2-isoproviroxycarbonylethyl, 2- (t-butoxycarbonyl) ethyl, 2-phenoxycarbonylethyl, 2-aminoaminocarbonyl Ethyl, 2- (N-methylaminocarbonyl) ethyl, 2- (N, N-dimethylaminocarbonyl) ethyl, 2- (N-ethylaminocarbonyl) ethyl, 2- (N, N-ethyl Aminocarbonyl) ethyl, 2- (N-n-propylaminocarbonyl) ethyl, 2- (N, N-di-n-propylaminocarboyl) ethyl, 2- (N-isopropylaminocarbonyl) ethyl And 2- (N-t-butylaminocarbonyl) ethyl, 2 (N-phenylaminocarbonyl) ethyl, 2- (N-phenylamino-methylaminocarbonyl) ethyl, benzyl and phenethyl.

In the following, G ¹ G ² , R ¹ , A ¹ and Q ¹ And the meaning of the term shown as the substituent of the "aliphatic hydrocarbon group". In addition, they have the same meaning in this specification unless otherwise specified.

 Examples of the halogen atom include fluorine, chlorine, bromine and iodine. Preferably, they are fluorine and chlorine.

 Examples of the lower alkoxy group include C 1 to C 8 alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, neobutoxy, t-butoxy, pentoxy and isopentoxy.

 The above-mentioned halogenated lower alkoxy group includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy substituted by one or more halogen atoms (eg, fluorine, chlorine, bromine and iodine). , Neobutoxy, t-butoxy, pentoxy and isopentoxy, and the like. Specifically, preferred are fluoromethoxy, chloromethoxy, difluoromethoxy, tolufluoromethoxy, trichloromethoxy, 2-bromoethoxy, 1,2-dichloromethylpropyl and the like.

 As the above lower alkenyloxy group, the lower alkenyl group has the same meaning as defined above. For example, vinyloxy, aryloxy, 1-propenyloxy,

2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy,

And C2-C7 alkenyloxy such as 3-butenyloxy and 2-ethyl-1-butenyloxy.

 Examples of the halogenated lower alkenyloxy group include one or two or more substituted with a halogen atom (eg, fluorine, chlorine, bromine, and iodine). For example, vinyloxy, aryloxy, and C2-C7 alkenyloxy groups such as niloxy, 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy and the like. .

As the above lower alkynyloxy group, the lower alkynyl has the same meaning as defined above, for example, 1-propynyloxy, 2-propynyloxy and 2- Penten-1 41-nylonoxy.

 Examples of the substituent of the above-mentioned optionally substituted phenyl lower alkyloxy group include the same as those exemplified as the substituent of the aliphatic hydrocarbon group which may be substituted in the lower alkyl portion, In the benzene ring portion, in addition to the same substituents as those exemplified for the optionally substituted aliphatic hydrocarbon group, a lower alkyl group, a halogenated lower alkyl group, a lower alkenyl group, a halogenated lower alkenyl group And lower alkynyl groups.

 Examples of the substituent of the phenyloxy which may be substituted include the same as those exemplified as the substituent of the aliphatic hydrocarbon group which may be substituted, and lower alkyl ¾ and halogenated lower. Examples include an alkyl group, a lower alkenyl group, a halogenated lower alkenyl group and a lower alkynyl group.

 As the above lower alkylthio group, the lower alkyl group is the same as defined above, and includes, for example, methylthio, ethylthio, η-propylthio, isopropyl, η-butylthio, t-butylthio and the like.

 Examples of the above aromatic hydrocarbon group include phenyl, indenyl, naphthyl (eg, 11-naphthyl and 2-naphthyl), anthryl, phenanthryl, acenaphthylenyl, fluorenyl (eg, 91-fluorenyl and 11-naphthyl). Aromatic hydrocarbon groups having 6 to 20 carbon atoms, such as fluorenyl and the like. Preferably, they are phenyl and naphthyl. More preferably, it is phenyl.

 Examples of the substituent for the aromatic hydrocarbon group include the same as those exemplified as the substituent for the aliphatic hydrocarbon group which may be substituted, a lower alkyl group, a lower alkenyl group, and a halogenated lower alkyl group. And lower alkenyl groups.

The above-mentioned optionally substituted heterocyclic group may be a monocyclic or polycyclic heterocyclic group, for example, selected from a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom. Examples thereof include a 5- to 10-membered monocyclic or polycyclic heterocyclic group containing from 4 to 4 hetero atoms as ring-constituting atoms. It also includes complexes containing copper atoms. You.

 Examples of the substituent of the above-mentioned heterocyclic group include the same as those exemplified as the substituent of the optionally substituted aliphatic hydrocarbon group, a lower alkyl group and a lower alkenyl group. And halogenated lower alkyl groups and halogenated lower alkenyl groups.

Specific examples of the monocyclic heterocyclic group include, for example, isoxazolyl, isothiazolyl, imidazolyl, 1,2,3-oxdiazolyl, 1,3,4-oxodiazolyl, oxazolyl, furzanil, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, thiazolyl, chenyl, tetrazoril, triazinyl, 1,2,3-triazolyl, 1,2,4-triazolyl , Bilanyl, pyrazinyl, virazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrrolyl, 2H-pyrrolyl, furazanil, furyl and the like. Specific examples of the condensed polycyclic heterocyclic group include, for example, acrylidinyl, 5-azabenzo [a] anthracenyl, isoindryl, isoquinolyl, isochromanyl, Isobenzofuranyl, imidazo [2,1-b] thiazolyl, 4H-imidazo [4,5-d] thiazolyl, imidazo [1,2-b] [1,2,4] triazi Nil, imidazo [1, 2-a] pyridyl, imigzo [1, 5-a] pyridyl, imidazo [1, 2-b] pyridazinyl, imidazo [1, 2-a] pyrimidinyl, imidazoli Dinyl, imidazolinyl, 1H-indazolyl, indridinyl, indril, 4H [1,3] oxoxathiol [5,4-b] pyrrolyl, 1H-2-2-year-old oxapyrenyl, power Rubazolyl, Hiichicarbolinyl,? -Carbolinyl, γ-carbo Nil, quinazolinyl, quinoxalinyl, quinolyl, chromanyl, 4H—1,3-dioxolo [4,5—b] imidazolyl, cyclopentyl [b] viranyl, 2,3-dithia-1,1,5-diazadanil, 4 H-1,3-dithianaphthalenyl, .1,4-dithianaphthalenyl, cinnoel, thianthrenyl, thieno [2,3-b] furanyl, 2,7,9-triazaphenanthrenyl, 1,2, 4—Triazo mouth [4,3-a] pyridazinyl, 1,2,4—Triazolo [4,3-a] pyridin 2,4,6 — Tritia 1 3a, 7a —Diazadanilnaphthyridinyl, piperazinyl, piperidyl, virazolidinyl, 7H-virazino [2,3-c] force rubazolyl, virazino [2, 3—d] pyridazinyl, 1 H—pyrazo mouth [4,3-d] oxazolyl, pyrazo mouth [1, 5—a] pyridyl, pyrido [1 ′, 2 ′: 1, 2] imidazo — B] Quinoxalinyl, 5 H —pyrid [2,3_d] 1 o —oxazinyl, 4 H —pyrido [2,3—c] Power rubazolyl, pyrrolidinyl, piplinyl, 1 H —pyrolipid [1,2-b] [2] Benzozepinyl, Pyro mouth [1,2-b] Pyridazinyl, phenazinyl, phenatridinyl, phenatrolinyl, phenoxazinyl, phenoxathiinyl, phenothiazinyl, phthalazinyl, pterydinil Zinyl, Purinyl, 2H-furo [3,2_b] vilanyl, furo [3,4-c] cincinolinyl, 1,2-benzoisoxazolyl, benzo [h] isocnolyl, 1,2-all Benzoisothiazolyl, benzimidazolyl, benzoxazolyl, 4H-3,1 benzoxazinyl, 3—benzoxepinyl, benzothiazolyl, benzo [b] phenyl, 1H benzotriazolyl, benzo [b ] Furanyl, morpholinyl and the like.

 The above-mentioned optionally substituted heterocyclic group may be a divalent group. Preferred specific examples of the divalent group of the unsubstituted heterocyclic group include, for example,

Is mentioned.

 Preferred examples of heterocyclic groups when they are monovalent are, for example, piperidinyl, 1,3-dioxolanyl, pyridyl, tetrahydro-2H-viranyl, and 1H-isoinyl Drills (eg, 1H-isoindole 1,3 (2H) dione, etc.).

 As the above mono-lower alkylamino group, the lower alkyl group has the same meaning as defined below. For example, C1-C8 monoalkylamino such as methylamino, ethylamino, n-propylamino, isopropylamino and n-butylamino. And a no group. Preferably, it is methylamino.

Is the above-di-lower alkylamino amino group, a force ⁵ a lower alkyl group is defined below the same way, for example, Jimechiruami Bruno, Echirumechiruami Bruno, Jechiruami Bruno, di n - Puropiruami Bruno and methyl n - propylamino, etc. And a C 2 -C 16 alkylamino group. Preferably, it is dimethylamino.

 As the above-mentioned lower alkoxycarbonyl group, the lower alkoxy group is the same as defined above, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl And C 2 -C 8 alkoxycarbonyl groups such as t-butoxycarbonyl and the like. Preferably, it is methoxycarbonyl.

 Examples of the halogenated lower alkoxycarbonyl group include a lower alkoxycarbonyl group (as defined above) substituted with 1 to 5 halogen atoms (eg, fluorine, chlorine, bromine, and iodine). For example, fluoromethoxycarbonyl, 2-chloroethoxycarbonyl, 3-fluoro-n-propoxycarbonyl, 2-chloroisopropoxycarbonyl, 4-promo n-butoxycarbonyl, and fluoro-t-butoxycarbonyl, etc. And a C2-C7-halogenated alkoxycarbonyl group. Preferably, it is fluoromethoxycarbonyl.

As the above-mentioned lower alkenyloxycarbonyl group, the lower alkenyl group is Same definitions as described below, for example, C 3 to C 7 such as vinyloxycarbonyl, aryloxycarbonyl, isopropenyloxycarbonyl, 1-propenyloxycarbonyl, and 2-butenyloxycarbonyl. Alkenyloxy force A luponyl group is exemplified. Preferably, it is aryloxycarbonyl.

 As the halogenated lower alkenyloxycarbonyl group, the halogenated lower alkenyl group is the same as the definition described later, and includes, for example, 1 to 5 halogen atoms (eg, fluorine, chlorine, bromine and iodine). Forces including substituted lower alkenyloxycarbonyl groups 5, such as 2-fluorovinyloxycarbonyl, 3-fluoroallyloxycarbonyl, 3-chloroallyloxycarbonyl, 1-chloromethylvinyloxy C3-C7 halogenated alkenyloxycarbonyl groups such as carbonyl, 3-chloro-1-propenyloxycarbonyl, and 4,4 difluoro-2-butenyloxycarbonyl. Preferably, it is 31-fluoroallyloxycarbonyl.

 As the above-mentioned lower alkynyloxycarbonyl group, the lower alkynyl group is the same as the definition described later, and includes, for example, ethynyloxycarbonyl, 1-propynyloxycarbonyl, 2-propynyloxycarbonyl and 2- And C3-C7 alkynyloxycarbonyl groups such as pentene-4-ynyloxycarbonyl. Preferably, it is 2-propynyloxycarbonyl.

 Examples of the substituent of the optionally substituted phenyloxycarbonyl group include the same as those exemplified as the substituent of the optionally substituted aliphatic hydrocarbon group, as well as a lower alkyl group and a halogenated group. Lower alkyl groups, lower alkenyl groups, halogenated lower alkenyl groups and lower alkynyl groups are exemplified.

The lower alkyl moiety of the above lower alkanoyloxy group is the same as defined below, for example, acetyloxy, ethylcarbonyl joxy, n-propylcarbonyloxy, isopropylcarbonyloxy, n-butyl Carbonyloxy, isobutylcarbonyloxy, t-butylcarbonyloxy, n-pentylcarbonyloxy, isopentylcarbonyloxy, neopentylcarboxy And C 2 -C 7 alkylcarbonyloxy such as roxy, t-pentylcarbonyloxy and hexylcarbonyloxy. Preferably, it is acetyloxy.

 Examples of the optionally substituted carbamoyl include carbomoyl, N-mono-lower alkyl rubamoyl, N, N-di-lower alkyl rubamoyl, N-hydroxycarbamoyl, and N-lower alkoxy N-hydroxyl N-lower alkyl N-lower alkoxy-N-lower alkylcarbamoyl, N-phenylcarbamoyl, N-phenyl N-lower alkylcarbamoyl and N-substituted And a phenylcarbamoyl group. The lower alkyl group and the lower alkoxy group in these are the same as those described below or as defined above. Preferred are sorbamoyl, N-methylcarbamoyl, N, N-dimethyl rubamoyl and N-phenyl N-methylcarbamoyl.

 Examples of the above-mentioned optionally substituted sulfonyl include, for example, an alkylsulfonyl group (eg, methylsulfonyl, ethylsulfonyl, and n-propylsulfonyl), phenylsulfonyl, and hydroxystylsulfonyl And the like. Preferred are methylsulfonyl and phenylsulfonyl.

 Examples of the silyl which may be substituted include, for example, C1-C15 mono-, di- or tri-lower-alkylsilyl and mono-, di- or tri-methylsilyl, dimethylsilyl and trimethylsilyl. And halogenated lower alkylsilyl. Preferably, it is trimethylsilyl.

The alicyclic hydrocarbon group of the alicyclic hydrocarbon group which may be substituted is a saturated or unsaturated monocyclic or polycyclic alicyclic hydrocarbon group, for example, cycloalkyl And cycloalkenyl groups and alkadienyl groups. Examples of the substituent of the alicyclic hydrocarbon group include the same as those exemplified as the substituent of the optionally substituted aliphatic hydrocarbon group, and a lower alkyl group and a lower alkenyl group. And halogenated lower alkyl groups and halogenated lower alkenyl groups. Examples of the cycloalkyl group include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, Bicyclo [3.2.1] octyl, bicyclo [3.2.2] nonyl, bicyclo [3.3.1] nonyl, bicyclo [4.2.1] nonyl, bicyclo [4.3.1] decyl, And a cycloalkyl group having 3 to 20 carbon atoms such as adamantyl. Preference is given to pentyl and cyclohexyl.

 Examples of the cycloalkenyl group include, for example, 2-cyclopentyl-1-yl, 3-cyclopentene-1-yl, 2-cyclohexene-1-yl, 3-cyclohexene-1-yl And cycloalkenyl groups having 4 to 20 carbon atoms, such as benzyl.

 Examples of the cycloalkadienyl group include, for example, 2,4-cyclopentene-1-yl, 2,4-cyclohexadiene-11-yl, and 2,5-cyclohexyl. And a cycloalkyl alkadienyl group having 4 to 20 carbon atoms such as Sagen-1-yl.

 Examples of the above phosphoric acid residue include 1 P O (0E t) 2 and the like.

Hereinafter, particularly preferred examples of substituents of aromatic hydrocarbon groups, heterocyclic groups, alicyclic hydrocarbon groups, phenyloxy and phenyloxycarbonyl groups, or "aliphatic hydrocarbon groups" The lower alkyl group, the lower alkenyl group, the haegenated lower alkyl group, and the haegagenated lower alkenyl group will be described. Examples of the lower alkyl group include C1 to C8 alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isoptyl, s-butyl, and t-butyl. Preferred are methyl, ethyl, and n-propyl. -Examples of the lower alkenyl group include vinyl, aryl, isoprobenyl, 1-propenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-ethyl. — 1-butenyl, and 3-methyl-2-butenyl, etc. Is mentioned. Preferably, vinyl and aryl are used.

 Examples of the halogenated lower alkyl group include, for example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, chlorofluoromethyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 1-fluoroethyl, 2-chloroethyl, and 1-chloroethyl. 1-chloroethyl, 2,2-dichloroethyl, 1,2-dichloroethyl, 1,1-dichloroethyl, 2-chloro-1 1-fluoroethyl, 1-chloro-1-, 2-fluoroethyl, 1,1-dichloro1-2,2-difluoroethyl, 1,2-dichloro-1,2-difluoroethyl and 2,2-dichloro-1,1-difluoroethyl.

 Examples of the halogenated lower alkenyl group include, for example, 1-fluoroallyl, 1-chloroallyl, 1-bromoallyl, 3-fluoro-1-propenyl, 3-chloro-11-propenyl, and 3-promoly-1-propyl Benyl and the like.

The “optionally substituted lower alkoxycarbonyl group” represented by G ¹ and G ² is the same as those exemplified as the substituent of the “optionally substituted aliphatic hydrocarbon group”.

Examples of the substituent of “optionally substituted amino” represented by R ¹ include a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a halogenated lower alkenyl group, a lower alkylcarbonyl group, and a lower alkyl group. And an alkoxycarbonyl group. Preferred specific examples of "optionally substituted amino" include amino, mono-lower alkylamino group (eg, methylamino, ethylamino and n-propylamino) and di-lower alkylamino group (eg, dimethylamino and getylamino). Etc.).

The “optionally substituted alicyclic hydrocarbon group” for R ¹ is the same as those exemplified as the substituent for the “optionally substituted aliphatic hydrocarbon group”.

The `` optionally substituted aromatic hydrocarbon group '' represented by R <sup>1</sup> and A 1 is exemplified as the substituent of the `` optionally substituted aliphatic hydrocarbon group '' Is the same as

The “optionally substituted heterocyclic group” for R ¹ is the same as those exemplified as the substituent for the “optionally substituted aliphatic hydrocarbon group”. Preferably, arbitrary preferable if G ¹ and G ² are identical.

Preferably, G ¹ is OR ¹ .

 Preferred examples of the compound (I) used in the present invention are shown in Tables 1 to 8. Further preferred compounds used in the test examples are as follows.

 Diisopropyl squarate (Example 1), diaryl squarate (Example 2), dibenzyl squarate (Example 3), tert-butyl squarate (Example 4), t-butylmethyl Squarate (Example 4), getyl squarate (Example 5), di-3-pentane squarate (Example 6), G1,3-dimethylbutane squarate (Example 7), 2- (1-Methylethoxy) 1,3-dioxo-1-cyclobutene-1 methyl monoacetate (Example 8).

As the salt of the compound of the present invention, a pharmacologically acceptable salt is preferable, and for example, a salt with an inorganic base, a salt with an organic base, a salt with an inorganic acid, a salt with an organic acid, and a salt-soluble salt. Or acid amino salts. Salts with inorganic bases include alkali metal salts such as sodium salts and potassium salts, alkaline earth metal salts such as calcium salts, magnesium salts and barium salts, and aluminum salts and ammonium salts. . Salts with organic bases include salts with trimethylamine, triethylamine, pyridine, picolin, ethanolamine, diethanolamine, triethanolamine, dicyclohexylamine, and N, N'-dibenzylethylenediamine. Is mentioned. Salts with inorganic acids include salts with hydrochloric acid, hydrofluoric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, perchloric acid, hydroiodic acid and the like. Salts with organic acids include formic acid, diacid, upper trifluoroacetic acid, fumaric acid, oxalic acid, tartaric acid, maleic acid, citric acid, succinic acid, malic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, methane acid Examples thereof include salts with sulfonic acid, p-toluenesulfonic acid, and benzenesulfonic acid. Basic Ami Salts with carboxylic acids include salts with arginine, lysine, and orditin, and salts with acidic amino acids include salts with aspartic acid, glutamic acid, and the like.

The hydrate of the compound of the present invention is preferably a pharmacologically acceptable hydrate, and also includes a hydrate. Specifically, monohydrate, dihydrate, hexahydrate and the like can be mentioned. These salts and hydrates can be prepared according to a conventional method. Tables 1 to 69 below show combinations of the substituents R ¹ and R ² of the preferred compounds as the pest controlling agent of the present invention in the case of the following general formula (II).

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 iHSOOOOSHO dSHO 66

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HOOOSHO ΛΖΗΟ 96 MdOSHO dZUO S6

 HO≡OSHOOSHO dZUO Z6

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 SHO = HOSHOOSHO JSHO 06

 iHSOOSHO dZUO 68

 SHSOOSHO ΛΖΗΟ 88 91 SJOOSHO dZU19 19 SJHOOSHO dZUO 98

 iSHOOSHO ΛΖΗΟ 38

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 226 CHF2 CH2CH2CON (C2H5) 2

227 CHF2 CH2CH2CONHC3H7

228 CHF2 CH2CH2CON (C3H7) 2

229 CHF2 CH2CH2CONH-isoPr

230 CHF2 CH2CH2CONH-tortBu

231 CHF2 CH2CH2CONHPh

232 CHF2 CH2CH2CONCH3Ph

233 CHF2 CH2Ph

 234 CHF2 CH2CH2Ph

 235 CF3 H

 236 CF3 CH3

 237 CF3 CH2F

 238 CF3 CHF2

 239 CF3 CF3

 240 CF3 CH20CH3

 241 CF3 CH20CH2F

 242 CF3 CH20CHF2

 243 CF3 CH20CF3

 244 CF3 CH20C2H5

 245 CF3 CH20C3H7

 246 CF3 CH20CH2CH = CH2

247 CF3 CH20 CH2CF = CF2

248 CF3 CH20CH2C = CH

249 CF3 CH20-isoPr

250 CF3 CH20-isoBu

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Compound number Rl R2

 976 CH2NH2 CH2CH2F

977 CH2NH2 CH2CHF2

978 CH2NH2 CH2CF3

 979 CH2NH2 CF2CF3

980 CH2NH2 CH2CH20CH3

981 CH2NH2 CH2CH20CH2F

982 CH2NH2 CH2CH20CHF2

983 CH2NH2 CH2CH20CF3

 984 CH2NH2 CF2CF20CF3

 985 CH2NH2 CH2CH20 C2H5

986 CH2NH2 CH2CH20CF2CF3

987 CH2NH2 CH2CH20C3H7

988 CH2NH2 CH2CH20CH2CH = CH2

989 CH2NH2 CH2CH20CH2CF = CF2

990 CH2NH2 CH2CH20 CH2C≡CH

991 CH2NH2 CH2CH20-isoPr

992 CH2NH2 CH2CH20-tertBu

993 CH2NH2 CH2CH20Ph

994 CH2NH2 CH2CH20CH2Ph

995 CH2NH2 CH2CH2COOH

996 CH2NH2 CH2CH2COOCH3

997 CH2NH2 CH2CH2COOC2H5 "

998 CH2NH2 CH2CH2COOC3H7

999 CH2NH2 CH2CH2COO-isoPr

1000 CH2NH2 CH2CH2COO-ertBu OM oszio so / 66

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 (〇H3H CH〇〇C

 (CH〇HΩΚ ΩΟΟ

CHWCNHHHO) H C2〇2 〇HH〇〇3

 2〇H2HCH 〇HCON

 () HCH2 CHC3〇〇〇HCH2CNH CO

 咪 φ

Ϊ 6 o

0

AV O / J3

 ^ S 9

I

〇 HHo〇〇c〇SO¾ _ Table 6 9

 Compound number Rl R2

 1701 CH (CH3) COOPh CH2CH2COO-isoPr

 1702 CH (CH3) COOPh CH2CH2COO-t.ert.Bu

 1703 CH (CH3) COOPh CH2CH2COOPh

 1704 CH (CH3) COOPh CH2CH2CONH2

 1705 CH (CH3) COOPh CH2CH2CONHCH3

 1706 CH (CH3) COOPh CH2CH2CON (CH3) 2

 1707 CH (CH3) COOPh CH2CH2CO NHC2H5

 1708 CH (CH3) COOPh CH2CH2CON (C2H5) 2

 1709 CH (CH3) COOPh CH2CH2CONHC3H7

 1710 CH (CH3) COOPh CH2CH2CON (C3H7) 2

 1711 CH (CH3) COOPh CH2CH2CONH-isoPr

 1712 CH (CH3) COOPh CH2CH2CONH-tert.Bu

 1713 CH (CH3) COOPh CH2CH2CONHPh

 1714 CH (CH3) COOPh CH2CH2CONCH3Ph

 1715 CH (CH3) COOPh CH2Ph

 1716 CH (CH3) COOPh CH2CH2Ph

The compound (I) used in the present invention is not particularly limited, but can be produced and prepared by a known method for synthesizing a cyclobutenedione derivative. For example, Japanese Patent Application Laid-Open Nos. 51-113053, J. Am. Chem. Soc. 96, 2267 (1974), Angew.Chem. 78.927 (1966), Gazz.chim.ital. 102, 818 (1972), Angew.Chem. 75, 982 (1963), Ange w.Chem. 78, 927 (1966), Ann.Chem. 686.55 (1965), Ann.Ghem. 742, 116 (1970), J. Am. Chem. Soc. 88, 1533 (1966), J. Am. Chem. Soc. 96, 3006 (1974), Tetrahedron Letters. 10 .. 1970. S. 781, Angew. Chem. 8i, 917 ( 1969), Ange w. Chem. 84.480 (1972), Angew.Chem. 84: 481 (1972), Beri.Dtsch.Chem.G os.cliff. 3553 (1970), Beri.Dtsch.Chem. Ges. 104.873 (1971), Science.179.

87, 491 (1975), J. Am. Chem. Soc. 81. 2678 (195 9), J. Org. Chem. 25.1008 (1963), Angew. Chem. 86 , 574 (1974), Chemistry Letters. 1972. 927, J. Org. Chem. 32. 3703 (1967), and Bull. Soc. Chim. France. 1974. 529.

 In addition, Tetrahedron.Letters.38 (40) .7091-7094.1997, J.Am.Chem.Soc, 119.12125-12130.1997, Biosci.46 (5-6), 498-501.1991, Synth.Commun..27.2177- 2180.1997, Synthesis. 961-993. December 1980¾ ^ 'J.Org.Chem., GO.1470-1472.1995.

 Examples of nematode poles include plant parasitic nematodes, insect palatability and nematode parasitic nematodes (eg, Mannozacentiyu and Rhiinaphelenchus etc.), animal parasitic lines, and landscaping lines. Insects and the like.

 Examples of the plant to which the nematocide of the present invention is applied include various cultivated plants, such as sugar beet, pineapple, soybean, peanut, evening onion, sprouts, radish, carrot, carp, cucumber, fig, strawberry, lingo, In addition to trees, green onions, tobacco, chisha, pepper, and chrysanthemum, trees (eg, pine, palm), and pasture.

 The nematocide to which the present invention is applied may be a human animal (eg, a pig, a sheep, a pig, a goat, a chick, a turkey, a pike, and a heron). For example, mammals such as dogs, cats, and dogs), birds, amphoteric, reptiles, or fish.

Examples of nematodes to which the nematocide of the present invention acts include, for example, Aralia cricket centipede, Ishuku-Senyu, Strawberry-Senyu, Rice-Singare-Cenyu-yu, Insect-Insect-Rice, Inesi-Senchi-Senyu, and Imogsarecentiyu. , Ogata-Kari-Senyu, Kai-Chu, Kiku-Hagare-Senyu, Kiku-Negare-Senyu, Kuki-Senyu, Klumineg-Sales-Cenyu, Wong-Gip-Senyu, Satsuma-mon-Kone-Senyu, Shihenchu-yu, Potato-M. Da Izusis Tossinyu, Tossin Yu, Tonensis Tossinyu, Tosekisenchu, Nagaharisinyu, Nami Takisinyu, Nisenekobusenyu, Nisenexaresentienyu, Negusarecentiyu, Nekobusentiyu, Nemogrysentou, Pengsenthus Examples include Zicentiyu, Mikanneshiiyu, Minaminegusarecentiyu, Mugishisutosentiuyu, Yumi-no-Pericentiyu, Racencentiyu, and Zicentiyu.

 Therefore, the preparation containing the compound according to the present invention is useful as a nematicide for agricultural and animal use.

 Except for nematocide II, application as an insecticide or soil disease control agent, such as soil damage mountain, soil damage (e.g., sheath blight, wilt, silk blight, ^ blight) , Vine disease, and wheat mosaic disease).

 The nematocide of the present invention includes at least a compound represented by the general formula (I) or the like, which is used in 0.1.

It contains 1 to 9511% by weight, preferably 2 to 80% by weight. These nematicides can be used i.i alone or diluted. The method of use and the degree of use vary depending on the purpose of use, the target plant or animal, the WI used, the type of soil, etc., and are generally as follows. For example, 10 to 50 kg per 10 a in a granular formulation is totally mixed with soil up to a depth of about 20 cm from the surface. The nematocide of the present invention is used in an amount of 10 g to 100 kg, preferably 10 ° to 20 kg per 10 a. If the treated surface is too wide, there is a method of mixing with a tractor or mixing with irrigation water to penetrate the soil.

 In general, the formulations comprise at least one compound of the invention (I) of from 0.1 to 95% by weight, preferably from 2 to 80% by weight. These preparations can be used alone or diluted. The concentration used varies depending on the purpose of use and the time of use. In general, it is used in the range of about 1 to 5,000, preferably about 100 to 5, and about OO ppm. The compound (I) of the present invention is used at about 10 g to 5 k / hemi tar, preferably at about 100 g to 1,000 / hemi tar.

When using this nematicide, mix it with various carriers according to the scene of use. For example, they can be used as granules, wettable powders, emulsions, suspensions and the like.

 The embodiments as described above comprise at least one compound of the invention and suitable solid or liquid carriers and, if desired, suitable auxiliaries for improving the dispersibility and other properties of the active substance. (For example, a surfactant, a spreading agent, a dispersing agent, a stabilizing agent, a dispersing agent, a suspending agent, a penetrating agent, a wetting agent, etc.) and can be obtained by a usual method. Examples of solid carriers or diluents include botanicals (eg, cereal flour, tobacco stalk flour, soy flour, walnut husk flour, vegetable flour, canna flour, bran, bark flour, fiber flour, vegetable Extraction residue), fibrous materials (eg, paper, corrugated cardboard, rags), artificial plastic powders, clays (eg, kaolin, diatomaceous earth, bentonite, clay, clay), talc and inorganic substances (eg, wax wax) Stones, mica, pumice, sulfur powder, activated carbon), and fertilizers (eg, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride). Liquid suspensions and diluents include water, alcohols (eg, methanol, ethanol), ketones (eg, acetone, methylethyl ketone), ethers (eg, getyl ether, dioxane, etc.). Sepasolve, Tetrahydrofuran), aromatic hydrocarbons (eg, benzene, toluene, xylene, methylnaphthalene), aliphatic hydrocarbons (eg, gasoline, kerosene, kerosene), esters, nitriles, Acid amides (eg, N, N-dimethylformamide, N, N-dimethylacetamide), halogenated hydrocarbons (eg, dichloroethane, carbon tetrachloride), sorbent naphtha, cyclohexane, and the like.

Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, polyethylene glycol ethers, and polyhydric alcohol esters. Examples of spreading or dispersing agents include casein, gelatin, starch, carboxymethyl cellulose, acacia, alginic acid, lignin, bentonite, molasses, polyvinyl alcohol, pine oil and agar. -Yes. Stabilizers include PAP (isopropyl phosphate mixture), tricresyl phosphate (TCP), tall oil, epoxy oil, surfactants, fatty acids and their esters. In addition to the above components, the formulations of the present invention can be used in admixture with other fungicides, insecticides, acaricides, or fertilizers. Further, the nematicide of the present invention can be used in combination with an insecticide, a bactericide, a fertilizer, a soil treatment agent (improving agent) and the like. Example

Hereinafter, the present invention will be described in more detail with reference to Examples and Test Examples, but the present invention is not limited thereto. The ¹ H-NMR (CDC 13) values described in the examples were measured at 27 OMhz and expressed in ppm (form) using tetramethylsilane as an internal standard in chloroform. Coupling constants (J) are indicated by Hz. In the data, s is a single line, d is a double line, t, is a triple line, q is a four way line, soxt is a six IE line, sept is a seven IB line, m is a multiple IE line, and brs is a wide line. To taste. Example 1 Manufacture of diisopropyl squarate

 Squaric acid (4 g, 35.1 mmol), anhydrous benzene (20 mL), and anhydrous 2-propanol (20 mL) were added to a reaction vessel equipped with a Dean-Stark apparatus. Heated to reflux. One hour later, the solvent (1 O mL) was removed from the Dean-Stark apparatus E, and then anhydrous benzene (5 mL) and anhydrous 2-propanol (5 mL) were added. After repeating the same operation three times, the mixture was further heated to reflux for 20 hours. The reaction solution was cooled to room temperature, ether (30 mL) was added, and the ether layer was washed with saturated aqueous sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain the title compound (5.4 g, 27.3 mmol) as white crystals (yield: 78%).

 Melting point 4 3 to 4 5 V

1H-NMR (300 MHz, CDC1 3) δ ppm:. 5.35 (. 2H, sept J = G.2) 1.47 (.. 1 2H d J = 6.2).

Example 2 Manufacture of diaryl squarate Squaric acid (11.5 g, 101 mmol), anhydrous benzene (50 mL), and anhydrous aryl alcohol (100 mL) were added to a reaction vessel equipped with a Dean-Stark apparatus. Heated to reflux. One hour later, after removing the solvent (10 mL) from the Dean-Stark apparatus, anhydrous benzene (5 mL) and anhydrous aryl alcohol (5 mL) were added. After repeating the same operation three times, the mixture was further heated and refluxed for 20 hours. The reaction solution was cooled to room temperature, and the residue obtained by evaporating the solvent under reduced pressure was purified by column chromatography (ethyl acetate / n-hexane: 1/4 to 1/2). The compound (10.7 g, 55.1 mmol) was obtained as a yellow oil (yield 55%).

_{IH-NMR (300MHz CDC1 3.} ) Δ ppm:.. 6.04 (.. 2H ddd, J = 17.1, 10.4 6.2), 5.50 (211. (1. J = 17.1) 5.41 (2H, dJ = 10.4) 5.14 ( 4H, d. J = 6.2). Example 3 Production of dibenzyl squarate

 To a solution (500 mL) of an aqueous solution of squaric acid (11.4 g, 100 mmol) was added one specified sodium hydroxide until the pH became neutral (pH 7-8). At room temperature, silver nitrate (34.0 g, 200 mmol) was added. The resulting brown silver salt was collected by filtration, washed with water, acetone, and ether, and dried under reduced pressure. Benzyl chloride (48 mL, 41.7 mmol) was added to the obtained silver salt ether solution (200 mL), and the mixture was heated under reflux for 2 hours. After separating the precipitate, the filtrate was concentrated under reduced pressure to obtain a white solid suspension. The obtained residue was recrystallized from n-hexane to give the title compound (13.5 g, 45.9 mmol) as white crystals (yield 46%).

 Melting point 66 ° C

IH-NMR (300 MHz, CDC1 3) δ ppm: 7.2 (10 H, m), 5.6 (4H, s).

Example 4 Production of di-butyl squarate and methyl butyl squarate

In a reaction vessel equipped with a Dean-Stark apparatus, squaric acid (6.8 g, 60.0 mmol), anhydrous methyl orthoformate (70 mL), and anhydrous tertiary alcohol (2 4 OmL) and heated to reflux. One hour later, the solvent (10 mL) was removed from the Dean-Stark apparatus, and then anhydrous methyl orthoformate (5 mL) and anhydrous Yuichi Sharibe Yunoru (5 mL) were added. After repeating the same operation three times, the mixture was further heated under reflux for 2 hours. The reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the residue obtained was purified by column chromatography (ethyl acetate / n-hexane: 1/9 to 1/2). Sharpyl squarate (7.6 g, 33.4 mmol) as white crystals (56%) and methyl tert-butyl squarate (1.6 g, 8.9 mmol) as white crystals (Yield 15%).

 Dibutyl butyl squarate:

 Melting point 104 to 105 ° C

 1H-NMR (300 MHz. CDC13) c5 ppm: 1.62 (18H.s).

 Methyl tertiary butyl squarate:

 Melting point 89-90 ° C

 1H-NMR (300 MHz, CDC) δ ppm: 4.32 (3H, s), 1.51 (9H. S). Example 5 Production of getylsquarate

In a reaction vessel equipped with Dean-Stark equipment, squaric acid (5.0 Og, 44 mmol), anhydrous benzene (5 OmL), and absolute ethanol (5 OmL) were added and heated to reflux. did. One hour later, after removing the solvent (1 OmL) from the Dean-Stark apparatus, anhydrous benzene (5 mL) and absolute ethanol (5 mL) were added. After repeating the same operation three times, the mixture was further heated and refluxed for 20 hours. The reaction solution was cooled to room temperature, ether (3 OmL) was added, and the ether layer was washed with saturated aqueous sodium hydrogen carbonate and saturated saline. After drying the organic layer over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain the title compound (6.5 g, 38.5 mmol) as a yellow oily substance (yield 88%). 1H-NMR (300 MHz. CDC1 ₃ ) ό ppm: 4.75 (4H, q.J = 7.2), 1.49 (6H.t.

J = 7.2). Example 6 Manufacture of di-3-pentane square

 In a reaction vessel equipped with a Dean-Stark apparatus, squaric acid (1.7 g, 15.0 mmol), anhydrous benzene (1 O mL), and anhydrous 3-pentanol (15 mL) were added. And heated to reflux. One hour later, the solvent (1 O mL) was removed from the Dean-Stark apparatus, and then anhydrous benzene (5 mL) and anhydrous 3-pentanol (5 mL) were added. After repeating the same operation three times, the mixture was further heated and refluxed for 20 hours. The reaction solution was cooled to room temperature, and the residue obtained by evaporating the solvent under reduced pressure was subjected to column chromatography.

(Ethyl acetate / _n- hexane: 10-20 / 1) to give the title compound (2.4 g, 9.6 mmol) as a yellow oil (yield: 64%).

 11I-NMR (300 MHz, CDC13) δ pm: 5.03 (2H. Quint. J = 6.1), 1.81-1.7 1 (8H.m). 0.98 (12H.t, J = 7.4). Of 1,3-dimethylbutanesquarate

 In a reaction vessel equipped with a Dean-Stark apparatus, squaric acid (11.4 g, 100 mmol), anhydrous benzene (150 mL), anhydrous 1,3-dimethylbutanol (10O ml), and the mixture was heated under reflux. One hour later, the solvent (1 OmL) was removed from the Dean-Stark apparatus, and then anhydrous benzene (5 mL) and anhydrous 1,3-dimethylbutanol (5 mL) were added. After repeating the same operation three times, the heat was further returned at 20 o'clock. The reaction solution is cooled to room temperature, and the residue obtained by evaporating the solvent under reduced pressure is purified by column chromatography (ethyl acetate / n-hexane: 1/20 to 1/10). The title compound (7.3 g, 26 mmol) was obtained as a yellow oily substance (yield 26%).

_{1H-NMR (300 MHz CDC1 3} .) Δ ppm:... 5.34-5.24 (2H, m), 1.80 - 1.64 (4 H. m) 1.49-1.40 (2H, m) 1.43 (6H d, J = 6.2 ), 0.95 (12H, d. J = 6.1). Example 8 Preparation of 2- (1 -methylethoxy) 1-3, 4-dioxo 1 1-six-butene--1 methyl monoacetate To a dichloromethane solution (5 mL) of diisopropyl squarate (100 mg, 0.50 mmol) was added methyl (triphenylphosphoranylidene) acetate (334 mg, 1.0 mmol). The mixture was stirred at room temperature for 48 hours. The residue obtained by evaporating the solvent under reduced pressure was purified by column chromatography (ethyl acetate / n-hexane: 1/4 to 1/2), and the alkylidene compound (118 mg, 0.4 6 mmol) was obtained as an isomer mixture of double bonds (E: Z = 2: 1) (yield: 92%). To a solution of the alkylidene compound (127 mg, 0.50 mmol) in dichloromethane (5 mL) was added 12 N hydrochloric acid (510). After stirring at room temperature for 48 hours, saturated aqueous sodium hydrogen carbonate was used. Was added, the aqueous layer was extracted three times with ethyl acetate (5 mL), the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give the title compound (74. (3 mg, 0.35 mmol) as a yellow oily substance (70% yield).

1H-NM (300 MHz.CDC1.)) C5 ppm: 5.44 (1H.sept, J = Gl), 3.77 (3 H, s), 3.65 (2H, s), 1.48 (6H, (1, J = 6.1 ). (Test method)

 Using the nematode CaenorhalKlitis elegans, an S-hama test was performed to examine the activity.

 (1) Selection of test nematodes

 Using Cacnorhabditis elegans N2 as a test nematode, stage III larvae were selected from a population in aseptic subculture (Sayere L. al, 1963) and tested.

 (2) Measurement of reaction rate

 50〃1 M-9 buffer (Brenner, 1974) purified water was added to one hole of whole slide glass, and about 10 test nematodes were transferred with a transplant needle into the buffer. A 500 ppm test solution (50〃1) prepared with the liquid was added, and the mixture was gently stirred to a final concentration of 250 ppm. The slide glass was placed in a moist chamber, kept at about 22 ° C, and the number of surviving insects was examined 24 and 48 hours later. The number of repetitions was set to 2 for one treatment, and the final concentration of the control agent was set to 200 ppm.

The most obvious response is the power of death, and the activity of living but extreme activity. Those that were visually inhibited from those in the untreated plot, such as those that were suppressed at the end or those that had a specific shape such as a coil or bend, were defined as reaction individuals. All of the compounds of Examples 1, 2, 4 (both), 5 and 8 had mortality after 24 hours.

100%. Even for the compounds of Examples 3 and 6, the reaction rate (including dead insects) after 48 hours was 100%.

 The reaction rate of the compound of Example 7 after 48 hours was 23.6%.

 Oxamyl used as a control showed a response rate (including dead insects) of 100% after 48 hours, and MITC showed a dead rate of 100% after 24 hours. Thus, the nematicide has approximately the same nematicidal activity as the control. Industrial profit ffl possibility

 The nematicide of the present invention has a novel skeleton as a nematicide, and is used to control various harmful nematodes.

Claims

The scope of the claims

 1. General formula (I):

[In the formula, each of 0 ^{1 and 2} is independently halogen, hydroxyl, lower alkoxy, halogenated lower alkoxy, lower alkenyloxy, halogenated lower alkenyloxy, carboxyl, A lower alkoxycarbonyl group, a mercapto, a lower alkylthio group, an aromatic hydrocarbon group or a heterocyclic group S (the aromatic hydrocarbon group and the heterocyclic group include a halogen, a hydroxyl group, a lower alkyl group, and a lower alkenyl group; Selected from the group consisting of halogenated lower alkyl groups, halogenated lower alkenyl groups, lower alkoxy groups, lower alkenyloxy groups, halogenated lower alkoxy groups, halogenated lower alkenyloxy groups, mercapto and lower alkylthio groups. Which may have 1 to 5 anionic groups) Hydrocarbon group, an optionally substituted lower alkoxycarbonyl group, or the formula: _ 0- R ¹ or the formula: group (wherein represented by over S- R ^1, R ¹ is hydrogen ^ child, Re their It may be substituted with an aliphatic hydrocarbon group, amino, alicyclic hydrocarbon group, aromatic hydrocarbon group, or heterocyclic group, or represented by the formula: — C 0 — A ¹ A group wherein A ¹ is an aliphatic hydrocarbon group or an aromatic hydrocarbon group which may be substituted, or a group represented by the formula: _ 0 — Q ¹ (wherein, Q ¹ is hydrogen A nematicide containing an atom or an aliphatic hydrocarbon group which may be substituted)))) or a salt thereof or a hydrate thereof.

2. The substituents of the aliphatic hydrocarbon group represented by R ¹ , A ¹ and Q ¹ each independently represent a halogen, a hydroxyl group, a lower alkoxy group, a halogenated lower alkoxy group, a lower alkenyloxy group, Halogenated lower alkenyloxy group, lower alkynyloxy group, optionally substituted phenyl lower alkyloxy group, substituted Phenyloxy, mercapto, lower alkylthio, amino, mono-lower alkylamino, di-lower alkylamino, carboxyl, lower alkoxy carbonyl, halogenated lower alkoxy carbonyl, lower alkenyloxy carbonyl, Halogenated lower alkenyloxycarbonyl group, lower alkynyloxycarbonyl group, optionally substituted phenyloxycarbonyl, optionally substituted aromatic hydrocarbon group, optionally substituted heterocyclic group , Lower alkenyl group, optionally substituted rubamoyl, cyano, optionally substituted sulfonyl, optionally substituted silyl, sulfo, optionally substituted alicyclic hydrocarbon group Or a phosphoric acid residue, as defined in claim 1, Insect repellent.

3. The E substituent of the aliphatic hydrocarbon group represented by R ¹ , A ¹ and Q ¹ independently represents a halogen, a hydroxyl group, a lower alkoxy S, a halogenated lower alkoxy group, a lower alkenyloxy group. Group, halogenated lower alkenyloxy group, mercapto, lower alkylthio group, amino, mono-lower alkylamino group, di-lower alkylamino group, carboxyl, lower alkoxycarbonyl group, aromatic hydrocarbon group or heterocyclic group (The aromatic hydrocarbon group and the heterocyclic group include a halogen, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a halogenated lower alkenyl group, a lower alkoxy group, a lower alkenyloxy group, Halogenated lower alkoxy group, Halogenated lower alkenyloxy group, mercapto and lower alkyl It may also be) Ru der have 1 to 5 substituents selected Ri by the group consisting of OH group, claim 1, wherein or nematicide of paragraph 2, wherein.

4. G ¹ and G ² forces each independently represent a group represented by the formula: 10—R ¹ or the formula: 1 S—R 1 (where R ¹ is a halogen, a hydroxyl group, a lower alkoxy group A halogenated lower alkoxy group, a lower alkenyloxy group, a halogenated lower alkenyloxy group, a mercapto, a lower alkylthio group, an amino, a mono-lower alkylamino group, a di-lower alkylamino group, a carboxyl, a lower alkoxycarbonyl group, or Phenyl (the phenyl is a halogen, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a halogenated lower alkenyl group, a lower alkoxy A lower alkenyloxy group, a halogenated lower alkoxy group, a halogenated lower alkenyloxy group, a mercapto and a lower alkylthio group, which may have 1 to 5 substituents). The nematicide according to any one of claims 1 to 3, which represents a lower alkyl group or a lower alkenyl group which may be substituted.

5. Even if R ¹ is a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a halogenated lower alkenyl group, a lower alkyl group substituted with a hydroxyl group, a lower alkoxy lower alkyl group, or The nematicide according to any one of claims 1 to 4, which is a good phenylalkyl group.

6. G ¹ and G ² forces each independently represent a group represented by the formula: 0—R ^{1 wherein} R ¹ is a lower alkyl group or a lower alkenyl group (the lower alkyl group and the lower alkenyl The group may have 1 to 3 substituents selected from the group consisting of halogen, hydroxyl and lower alkoxy, or benzyl or phenethyl (wherein the benzyl and phenethyl are halogen, hydroxyl, , Lower alkyl groups, lower alkenyl groups, halogenated lower alkyl groups, halogenated lower alkenyl groups, lower alkoxy groups, lower alkenyloxy groups, halogenated lower alkoxy groups, halogenated lower alkenyloxy groups, mercapto and lower Which may have 1 to 5 substituents selected from the group consisting of alkylthio groups). The nematicide according to any one of claims 1 to 5.

7. G ¹ and G ² are the same, nematicides according to any one of the items 1 to 6 wherein the claims.

8.0 ¹ Oyobi 0 ^2, it it independently, a main butoxy, ethoxy, isopropyl Okishi, t one-butoxy, 1 one Echirupuropokishi, Ariruokishi, 1, 3 _ dimethylcarbamoyl Rubutokishi or base Njiruokishi, The nematicide according to any one of claims 1 to 7.