WO2001068617A1 - Carbamoyltetrazolinones et herbicides - Google Patents

Carbamoyltetrazolinones et herbicides Download PDF

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Publication number
WO2001068617A1
WO2001068617A1 PCT/JP2001/002088 JP0102088W WO0168617A1 WO 2001068617 A1 WO2001068617 A1 WO 2001068617A1 JP 0102088 W JP0102088 W JP 0102088W WO 0168617 A1 WO0168617 A1 WO 0168617A1
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WIPO (PCT)
Prior art keywords
group
ring
iso
alkyl
substituted
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Application number
PCT/JP2001/002088
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English (en)
Japanese (ja)
Inventor
Masatoshi Ohnari
Koichi Nishio
Yasuhiro Sakurai
Katsushi Morimoto
Kunimitsu Nakahira
Nobuyuki Hamada
Tooru Ohki
Junko Noguchi
Shigeomi Watanabe
Original Assignee
Nissan Chemical Industries, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU2001241167A priority Critical patent/AU2001241167A1/en
Publication of WO2001068617A1 publication Critical patent/WO2001068617A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings

Definitions

  • the present invention relates to rubbamoylte trazolinones and pesticides containing them as an active ingredient, particularly herbicides.
  • An object of the present invention is to provide a pesticide, particularly a herbicide, having excellent potency, which comprises a potato rubamoyl tetrazolinone as an active ingredient.
  • the present invention relates to the following formula 1)
  • L 1 represents C R2R 3 ;
  • L 2 represents CR 4 R 5 , CR 4 R 5 CR 6 R 7 , CR 4 R 5 CR 6 R 7 CR 8 R 9 or CR RSC I ⁇ i C RSi C R'OR 11 ,
  • R 1 ′ is a phenyl group (provided that the phenyl group is a C 4 -4 alkyl group, a Ci 4 haloalkyl group, a 4 alkoxy group, a cyano group, a nitro group, and a halogen group. .
  • R 12 and R 13 are each independently hydrogen atom, C, - 6 alkyl group, C 3 - e a cycloalkyl group, C 3 - 6 cycloalkenyl group, C 2 - 4 alkenyl group, Ji 2 - 4 ⁇ Rukiniru group, - 4 haloalkyl groups, C 3 - 6 2 alkyl group substituted with a cycloalkyl group, - 4 alkoxy group -, (wherein, R 12 and R 13 are simultaneously C, never represents a 4 alkoxy group.) C Bok 4 alkoxy C, - 4 alkyl group,
  • alkyl group, C, - 4 haloalkyl group, an alkoxy group, Shiano group may be substituted by the same or different and one or more location substituent selected from the two-Toro groups and halogen atoms.
  • 6 dihydric mud represents an 2 H- pyran one 4-I group, provided that the nitrogen atom R 12 and R 13 bound a monitor 3 rather it may also be configured to 9-membered ring, oxygen atom, a sulfur atom, C, - 4 alkyl nitrogen atom which may be substituted with a group, a carbonyl group, a sulfonyl group or an unsaturated bond rather it may also be include Idei a ring C, - 4 rather it may also be substituted by an alkyl group, the ring is d - crosslink
  • 5- or 6-membered hetero ring is thiophene ring, furan ring, pyrrol ring, oxazole ring, thiazole ring, imidazole ring, isooxazole ring, isothiazole ring, pyrazole ring, 1,3,4-oxaziazo 1,3,4-thiadiazole ring, 1,3,4-triazole ring, 1,2,4-oxaziazol ring, 1,2,4-thiadiazol ring, 1,2 , 4-triazole ring, 1,2,3-oxaziazol ring, 1,2,3-thiadiazole ring, tetrazole ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, Represents a 1,3,5-triazine ring or a 1,2,4-triazine ring;
  • the present invention relates to a rubamoylte trazolinonone represented by the formula:, a pesticide containing the compound as an active ingredient, and a herbicide containing the compound as an active ingredient.
  • Me methyl group, Et: ethyl group, Pr—n: normal propyl group, Pr—iso: isopropyl group, Bu—n: normal butyl group, Bu—is 0: isobutyl group, Bu — Sec: secondary butyl group, Bu—ter: tertiary butyl group, Pen-n: normal pentyl group, Hex—n: normal hexyl group, Pr—eye: cyclopropyl group, Bu — Eye: cyclobutyl group, P en -cyc: cyclopentyl group, H ex— eye: cyclohexyl group, P h: phenyl group, P ip: piperidine 1-yl group, Pyrr: pyrrolidine 1 1-yl group, Morph: morpholin-1 1-yl group, Pyran: 3,6-dihydro-2H-pyran — 4-yl group, Pentene — eye: cyclopentene-1 1-yl group,
  • L 1 is CR 2 R 3
  • L 2 is CR 4 R 5 , CR 4 R 5 CR 6 R ⁇ CR 4 R 5 CR 6 R 7 CR 8 R 9 or CR 4 R 5 CR 6 R 7 CR 8 R 9 C R'OR 11 , R ', R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 1 .
  • R 11 and R 11 when L 1 -L 2 is CR 2 R 3 CR 4 R 5 , one or more of R ′, R 2 , R 3 , R 4 and R 5 are: R ', RRRR 5 when the LL 2 is CR 2 R 3 CR 4 R 5 CR 6 R 7, or any one of R e and R 7, L 1 - L 2 is CR 2 R 3 CR 4 R 5 CR 6 R 7 CR 8
  • R 9 at least one of R ', RR 3 , R 4 , R 5 , R 6 , R 7 , R * and R 9 , L 1 and L 2 are CR 2 R 3 CR 4 R 5 CR 6 R 7 CR 8 R 9 CR 'OR 11 when RR 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , RR 1 .
  • Preferred combinations of these substituents include, for example, when L 1 -L 2 is CR 2 R 3 CR 4 R S , one of RR 2 , R 3 , R 4 and R 5 is L 1 — When L 2 is CR 2 R 3 CR 4 R 5 CR 6 R 7 , one of R ′, R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is L 1 - when L 2 is CR 2 R 3 CR 4 R 5 CR 6 R 7 CR 8 R 9 R ', the R 2, R 3, R 4 , R 5, R 6, R 7, R 8 and R 9 If one of them is L 1 — L 2 is CR 2 R 3 CR 4 R 5 CR 6 R 7 CR 8 R 9 C R'OR 11 , R ', RR 3 , RR 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are Ph, 2-Ct Ph, 3-Cl-Ph, 4-Cl-Ph, 2,4-
  • 2-EtO-Ph, 3-EtO-Ph and 4-EtO-Ph are substituents selected from the group consisting of H, Me, F and CI.
  • L 1 one L 2 is CH 2 - CH 2 in which R 1 is Ph, 2- Cl-Ph, 3 -C1- Ph, 4-Cl-Ph, 2, 4-Cl 2 -Ph, 3 , 5- Cl 2 - Ph, 2 , 6- Cl 2 - Ph, 2, 3-Cl 2 - Ph, 2, 5-Cl 2 - Ph, 2- F-Ph, 3-F-Ph, 4-F -Ph, 2, 4-F 2 - Ph, 3, 5 - F 2 - Ph, 2_F- 4- CI- Ph, 2- Br-Ph, 3-Br-Ph, 4 - Br- Ph, 2 - Me -Ph ⁇
  • R 12 is an alkyl group having 1 to 4 carbon atoms and R 13 is Ph, 2- CI- Ph, 3- CI - Ph, 4-Cl-Ph, 2, 4-Cl 2 - Ph, 3, 5- Cl 2 -Ph, 2, 6 - Cl 2 - Ph, 2, 3- Cl 2 - Ph, 2, 5 - Cl 2 - Ph, 2- F_Ph, 3_F- Ph, 4- F_Ph, 2, 4-F 2 - Ph, 3, 5- F 2 - Ph, 2- F-4-C1- Ph , 2-Br- Ph, 3- Br-Ph, 4- Br-Ph, 2- Me-Ph, 3- Me- Ph, 4-Me- Ph, 2, 4-Me 2 -Ph, 3, 5- Me 2 -Ph, 2, 6-Me 2 - Ph, 2 , 3- Me 2 -P
  • the compound (1) of the present invention can be easily produced by the following Reaction Scheme 1.
  • L 1 LRR 12 and R 13 represent the same meaning as described above, and Z represents a halogen atom.
  • Reaction formula 1 shows a method for producing the compound (1) of the present invention by reacting a tetrazolinone (2) with a carbamoyl halide (3) in the presence or absence of a base.
  • (3) is usually used in a molar amount of 1 to 10 times, preferably 1 to 2 times the molar amount of (2).
  • the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate and sodium hydride, pyridine, 4-dimethylaminopyridine, triethylamine, N, N_dimethylaniline And organic bases such as 1,8-diazabicyclo (5.4.0) —7-indene (DBU); organic lithiums such as n-butyllithium and sec-butyllithium; and organic lithium amines such as lithium diisopropylamide. Dos.
  • the base is used usually in an amount of 0 to 10 moles, preferably 1 to 2 moles, relative to (2).
  • Solvent reacts There is no particular limitation as long as it is inert to water, but, for example, aliphatic or aromatic hydrocarbons such as hexane, cyclohexane, benzene and toluene, carbon tetrachloride, chloroform and 1,2-dichloroethane Halogenated hydrocarbons such as ethylene, ethers such as Jethyl ether, diisopropyl ether, dioxane and tetrahydrofuran, ketones such as acetone, methylethyl ketone and methyl isobutyl ketone, and acetone.
  • aliphatic or aromatic hydrocarbons such as hexane, cyclohexane, benzene and toluene, carbon tetrachloride, chloroform and 1,2-dichloroethane
  • Halogenated hydrocarbons such as ethylene, ethers such as Jethyl ether, diisopropy
  • Nitriles such as tonitrile and propionitol; acid amides such as N, N-dimethylformamide and N, N-dimethylacetamide; sulfur-containing polar solvents such as sulfolane; Phosphorus-containing polar solvents such as hexamethylphosphoramide, and organic bases such as pyridine.
  • the reaction temperature is usually from 90 to 200 ° C, preferably from 0 to 120 ° C.
  • the reaction time is generally 0.05 to 100 hours, preferably 0.5 to 10 hours.
  • synthesis examples of the compound of the present invention will be specifically described with reference to Examples and Reference Examples, but the present invention is not limited thereto.
  • Trimethylsilyl azide (2.30 g, 20.0 mm 01) was added at 90 ° C to 1-phenylcyclopropanecarboxylic acid chloride (3.00 g, 16.6 g). mm 0 1) was added dropwise over 0.5 hour, and the mixture was further refluxed for 1 hour. After cooling to room temperature, the boron trifluoride getyl ether complex (0,000) dissolved in trimethylsilyl azide (2.80 g, 25.0 mm 01) and 1,2-dichloroethane (25 ml) was used. 23 g, 1.6 mmo 1) were added and refluxed for 1.5 hours.
  • CDCU 0.50- 2.46 (m, 15H), 2.46-3.87 (m, 7H), 7.35 (s, 4H) 10 CDCh 1.24 (d, J 6.6Hz, 6H), 1.44 (s, 4H),
  • H9'9 f 'PS'S' (HAT ' ⁇ ) 6ms'o ⁇ ⁇ ⁇
  • N N Et Enter 0 1 OO o1 OO
  • n s 3 S PC S a: s n: DC s e c s: n:
  • the amount of the compound of the present invention applied as a herbicide varies depending on the application scene, application time, application method, weeds and cultivated crops, but generally, the amount of active ingredient is hectare. About 0.001 to 50 kg, preferably about 0.01 to 10 kg per (ha) is suitable.
  • the compound of the present invention can be used as a herbicide for paddy fields in any of soil treatment and foliage treatment under harbor water.
  • paddyweeds include paddyweeds (Al ismacanal iculatum), omodaka '(Sag tariatrifol ia), and pericae (Sagittariapygmaea).
  • the compound of the present invention can be used as a herbicide for upland fields in any of soil treatment, soil admixture treatment, and foliage treatment. It can also be applied to the control of various weeds on non-agricultural land such as athletic fields, open spaces and track ends.
  • the compound of the present invention may be mixed with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of preparation or spraying.
  • herbicides to be used in combination with the compound of the present invention include, for example, pyrazosulfuron-ethylZ (common name), bensulfuron-methyl (common name), and sinosulfuron / common name.
  • the compound of the present invention When the compound of the present invention is applied as a herbicide, it is generally mixed with an appropriate solid carrier or liquid carrier, and further, if desired, a surfactant, a penetrant, a spreading agent, a thickener, an antifreezing agent. Agent, binder, anti-caking agent or anti-decomposition agent, etc., in any dosage form such as liquid, emulsion, wettable powder, dry flowable, flowable, powder or granule It can be put to practical use.
  • any of the above dosage forms can be provided by being enclosed in a water-soluble package.
  • kaolinite As a solid carrier, for example, kaolinite, ⁇ , and others. Natural minerals such as irophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride; Synthetic silicic acid, synthetic silicate and the like can be mentioned.
  • liquid carrier examples include water, alcohols (ethylene glycol, propylene glycol, isopropanol, etc.), aromatic hydrocarbons (xylene, alkyl benzene, alkyl naphthalene, etc.), ethers (butyl sorbitol). etc.), Quai tons acids (Kisano down like cyclohexane), esters (y _ Puchiroraku tons, etc.), acid Ami earth (N _ Mechirupirori Don, N- Okuchirupirori dong, etc.) and vegetable oils (soybean oil, rapeseed oil, Cottonseed oil, castor oil, etc.).
  • solid and liquid carriers may be used alone or in combination of two or more.
  • the surfactant include polyoxyethylene alkyl ether, polyoxyethylene styrylphenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, and the like.
  • Non-ionic surfactants such as polyoxyethylene sorbitan fatty acid esters, and alkyl benzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, and naphthalene sulfonates Salts of formalin condensates of: formalin condensates of alkylnaphthalenesulfonic acids; polyoxyethylene alkylaryl ethersulfate or phosphate; polyoxyethylenestyrylphenylethersulfate Or ionic surfactants such as phosphates and alkylamine salts.
  • the content of these surfactants is not particularly limited, it is usually desirable that the content be in the range of 0.05 to 20 parts by weight based on 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.
  • composition examples of the present invention are not limited only to these.
  • "parts" Means parts by weight.
  • anti-caking agents include anti-caking agents, anti-decomposition agents, etc. (emulsions)
  • antifreezing agents include antifreezing agents and thickeners (dry flowables)
  • Liquid carrier 0.1 to 50 parts
  • the above is uniformly mixed and pulverized to obtain a wettable powder.
  • Nonionic surfactant Kao Corporation
  • wet pulverization is performed to obtain a flowable agent.
  • the above compound (A) means pyrazosul furon-ethyl (generic name), and DBSN means sodium dodecylbenzenesulfonate.
  • 0 is less than 5% wither
  • 1 is 5% or more and less than 25 96 wither
  • 2 is 25% or more and less than 50% wither
  • 3 is 50% or more and less than 75% wither
  • 4 is 7 5 to 5% is a 5-point rating indicating that withering occurs, and 95% or more indicates withering.
  • Table 5 shows the results.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Cette invention se rapporte à des carbamoyltétrazolinones, représentées par la formule générale (1); à des produits chimiques agricoles contenant ces composés; et à des herbicides contenant ces produits chimiques. Dans ladite formule, L1 représente CR2R3; L2 représente CR?4R5, CR4R5CR6R7¿ ou similaire; au moins un des éléments R?1, R2, R3, R4, R5, R6 et R7¿ représente phényle (pouvant être substitué par alkyle C¿1?-C4 ou similaire) et les autres représentent chacun séparément hydrogène, alkyle C1-C4 ou similaire; et R?12 et R13¿ représentent séparément hydrogène, alkyle C¿1?-C6, cycloalkyle C3-C6 ou similaire.
PCT/JP2001/002088 2000-03-16 2001-03-16 Carbamoyltetrazolinones et herbicides WO2001068617A1 (fr)

Priority Applications (1)

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AU2001241167A AU2001241167A1 (en) 2000-03-16 2001-03-16 Carbamoyltetrazolinones and herbicides

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JP2000-73571 2000-03-16
JP2000073571 2000-03-16

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WO2001068617A1 true WO2001068617A1 (fr) 2001-09-20

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5652198A (en) * 1995-03-10 1997-07-29 Nihon Bayer Agrochem K.K. Herbicidally active tetrazolinones
US5776858A (en) * 1995-10-31 1998-07-07 Nihon Bayer Agrochem K.K. 1-azinyl-tetrazolinones
US5874586A (en) * 1995-09-22 1999-02-23 Bayer Aktiengesellschaft Process for preparing 1-aryl-4-carbamoyl-tetrazolinones

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5652198A (en) * 1995-03-10 1997-07-29 Nihon Bayer Agrochem K.K. Herbicidally active tetrazolinones
US5874586A (en) * 1995-09-22 1999-02-23 Bayer Aktiengesellschaft Process for preparing 1-aryl-4-carbamoyl-tetrazolinones
US5776858A (en) * 1995-10-31 1998-07-07 Nihon Bayer Agrochem K.K. 1-azinyl-tetrazolinones

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