WO2000024250A1 - Derives de cyclobutenedione presentant des activites nematicides - Google Patents

Derives de cyclobutenedione presentant des activites nematicides Download PDF

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Publication number
WO2000024250A1
WO2000024250A1 PCT/JP1999/005776 JP9905776W WO0024250A1 WO 2000024250 A1 WO2000024250 A1 WO 2000024250A1 JP 9905776 W JP9905776 W JP 9905776W WO 0024250 A1 WO0024250 A1 WO 0024250A1
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group
halogenated
groups
alkenyloxy
optionally substituted
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PCT/JP1999/005776
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English (en)
Japanese (ja)
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Yoshio Hayase
Katsuaki Ohba
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Shionogi & Co., Ltd.
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals

Definitions

  • the present invention relates to a nematicide, which is a kind of agricultural or veterinary drug, particularly a cyclobutenedione derivative having nematicidal activity.
  • D-D (1,3-dichlorobronone), chloropicrin, oxamil, bromide, and methyl bromide are used for nematode control in soil and fumigants.
  • An object of the present invention is to provide a novel nematocide that is safe and low in toxicity.
  • the present invention is a.
  • 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
  • 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.
  • 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.
  • 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.
  • 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, Hal
  • 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
  • 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.
  • Phenyl 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).
  • 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).
  • lower 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.
  • 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.
  • 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, is
  • 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.
  • 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)
  • 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.
  • 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
  • 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).
  • a halogen, a hydroxyl group, a lower alkoxy group, and a phenyl 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,
  • 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.
  • halogen atom examples 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.
  • 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.
  • the lower alkenyl group has the same meaning as defined above.
  • C2-C7 alkenyloxy such as 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • halogenated lower alkenyloxy group examples include one or two or more substituted with a halogen atom (eg, fluorine, chlorine, bromine, and iodine).
  • a halogen atom eg, fluorine, chlorine, bromine, and iodine
  • 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.
  • 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 3 ⁇ 4 and halogenated lower. Examples include an alkyl group, a lower alkenyl group, a halogenated lower alkenyl group and a lower alkynyl group.
  • the lower alkyl group is the same as defined above, and includes, for example, methylthio, ethylthio, ⁇ -propylthio, isopropyl, ⁇ -butylthio, t-butylthio and the like.
  • aromatic hydrocarbon group examples include phenyl, indenyl, naphthyl (eg, 11-naphthyl and 2-naphthyl), anthryl, phenanthryl, acenaphthylenyl, fluorenyl (eg, 91-fluorenyl and 11-naphthyl).
  • substituent for the aromatic hydrocarbon group examples 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.
  • 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.
  • condensed polycyclic heterocyclic group examples 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
  • 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,
  • 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.).
  • the lower alkyl group has the same meaning as defined below.
  • C1-C8 monoalkylamino such as methylamino, ethylamino, n-propylamino, isopropylamino and n-butylamino.
  • a no group Preferably, it is methylamino.
  • 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.
  • 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.
  • it is methoxycarbonyl.
  • halogenated lower alkoxycarbonyl group examples include a lower alkoxycarbonyl group (as defined above) substituted with 1 to 5 halogen atoms (eg, fluorine, chlorine, bromine, and iodine).
  • halogen atoms eg, fluorine, chlorine, bromine, and iodine.
  • a C2-C7-halogenated alkoxycarbonyl group Preferably, it is fluoromethoxycarbonyl.
  • 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.
  • the halogenated lower alkenyloxycarbonyl 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.
  • 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.
  • 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.
  • 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.
  • optionally substituted sulfonyl examples include, for example, an alkylsulfonyl group (eg, methylsulfonyl, ethylsulfonyl, and n-propylsulfonyl), phenylsulfonyl, and hydroxystylsulfonyl And the like. Preferred are methylsulfonyl and phenylsulfonyl.
  • 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.
  • 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.
  • 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.
  • cycloalkyl group examples 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.
  • cycloalkenyl group examples 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.
  • cycloalkadienyl group examples include, for example, 2,4-cyclopentene-1-yl, 2,4-cyclohexadiene-11-yl, and 2,5-cyclohexyl.
  • 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.
  • lower alkyl group examples 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.
  • vinyl and aryl are used.
  • halogenated lower alkyl group examples include, for example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, chlorofluoromethyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 1-fluoroethyl, 2-chloroethyl, and 1-chloroethyl.
  • halogenated lower alkenyl group examples 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”.
  • 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 1 and A 1 is exemplified as the substituent of the ⁇ optionally substituted aliphatic hydrocarbon group '' Is the same as
  • R 1 is the same as those exemplified as the substituent for the “optionally substituted aliphatic hydrocarbon group”.
  • G 1 and G 2 are identical.
  • G 1 is OR 1 .
  • 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).
  • 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.
  • 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
  • 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).
  • 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.
  • nematode poles examples 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.
  • 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).
  • a human animal eg, a pig, a sheep, a pig, a goat, a chick, a turkey, a pike, and a heron.
  • mammals such as dogs, cats, and dogs
  • birds amphoteric, reptiles, or fish.
  • 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.
  • the preparation containing the compound according to the present invention is useful as a nematicide for agricultural and animal use.
  • 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).
  • soil damage mountain e.g., sheath blight, wilt, silk blight, ⁇ blight
  • Vine disease e.g., 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.
  • 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.
  • 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.
  • 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.
  • this nematicide 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.
  • suitable auxiliaries for improving the dispersibility and other properties of the active substance.
  • a surfactant, a spreading agent, a dispersing agent, a stabilizing agent, a dispersing agent, a suspending agent, a penetrating agent, a wetting agent, etc. can be obtained by a usual method.
  • 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).
  • 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 eg, clays (e
  • Liquid suspensions and diluents include water, alcohols (eg, methanol, ethanol), ketones (eg, acetone, methylethyl ketone), ethers (eg, getyl ether, dioxane, etc.).
  • alcohols eg, methanol, ethanol
  • ketones eg, acetone, methylethyl ketone
  • ethers eg, getyl ether, dioxane, etc.
  • surfactants include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, polyethylene glycol ethers, and polyhydric alcohol esters.
  • 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.
  • the formulations of the present invention can be used in admixture with other fungicides, insecticides, acaricides, or fertilizers.
  • 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 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.
  • stage III larvae were selected from a population in aseptic subculture (Sayere L. al, 1963) and tested.
  • 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 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.
  • the nematicide has approximately the same nematicidal activity as the control.
  • the nematicide of the present invention has a novel skeleton as a nematicide, and is used to control various harmful nematodes.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des nématicides efficaces pour l'extermination de différents nématodes, comprenant des composés représentés par la formule (I), des sels de ceux-ci ou des hydrates des deux. Dans cette formule, G1 et G2 représentent chacun indépendamment un hydrocarbyle aliphatique qui peut être substitué par un groupe représenté par la formule O-R?1 (où R1¿ représente hydrogène, hydrocarbyle aliphatique éventuellement substitué, ou analogue), ou un analogue.
PCT/JP1999/005776 1998-10-27 1999-10-20 Derives de cyclobutenedione presentant des activites nematicides WO2000024250A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10/304893 1998-10-27
JP30489398 1998-10-27

Publications (1)

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WO2000024250A1 true WO2000024250A1 (fr) 2000-05-04

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3275676A (en) * 1963-09-30 1966-09-27 Standard Oil Co Process for preparing cyclobutene-1, 2-dicyanide
JPS51130530A (en) * 1975-04-18 1976-11-12 Ciba Geigy Ag Weed killer also controlling plant growth and compound used
JPS5732268A (en) * 1980-06-25 1982-02-20 Bayer Ag N-acylated n-methyl-carbamic acid o-pyrazol- 4-yl esters, manufacture and use in vermin repellent
JPS5795993A (en) * 1980-10-16 1982-06-15 Basf Ag 2-fluorophenyl-(di)thiophosphoric acid ester, manufacture and insecticide containing same
JPS5852298A (ja) * 1981-08-28 1983-03-28 バスフ・アクチエンゲゼルシヤフト ３−フルオルフエニル−（ジ）チオリン酸エステル、その製造方法および該化合物を含有する害虫駆除剤
JPH03178945A (ja) * 1989-11-30 1991-08-02 Bayer Ag 部分的フツ素化アルコールの製造法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3275676A (en) * 1963-09-30 1966-09-27 Standard Oil Co Process for preparing cyclobutene-1, 2-dicyanide
JPS51130530A (en) * 1975-04-18 1976-11-12 Ciba Geigy Ag Weed killer also controlling plant growth and compound used
JPS5732268A (en) * 1980-06-25 1982-02-20 Bayer Ag N-acylated n-methyl-carbamic acid o-pyrazol- 4-yl esters, manufacture and use in vermin repellent
JPS5795993A (en) * 1980-10-16 1982-06-15 Basf Ag 2-fluorophenyl-(di)thiophosphoric acid ester, manufacture and insecticide containing same
JPS5852298A (ja) * 1981-08-28 1983-03-28 バスフ・アクチエンゲゼルシヤフト ３−フルオルフエニル−（ジ）チオリン酸エステル、その製造方法および該化合物を含有する害虫駆除剤
JPH03178945A (ja) * 1989-11-30 1991-08-02 Bayer Ag 部分的フツ素化アルコールの製造法

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