WO2001079200A1 - Derives de pyrazole et herbicides les contenant - Google Patents

Derives de pyrazole et herbicides les contenant Download PDF

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Publication number
WO2001079200A1
WO2001079200A1 PCT/JP2001/003232 JP0103232W WO0179200A1 WO 2001079200 A1 WO2001079200 A1 WO 2001079200A1 JP 0103232 W JP0103232 W JP 0103232W WO 0179200 A1 WO0179200 A1 WO 0179200A1
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group
atom
alkyl
represented
alkyl group
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PCT/JP2001/003232
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English (en)
Japanese (ja)
Inventor
Ichiro Nasuno
Mitsuru Shibata
Kazuyoshi Koike
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Idemitsu Kosan Co., Ltd.
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Priority to AU46920/01A priority Critical patent/AU4692001A/en
Publication of WO2001079200A1 publication Critical patent/WO2001079200A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to a novel pyrazole derivative and a herbicide using the same. More specifically, the present invention relates to a pyrazole derivative capable of controlling a wide range of field weeds at a low dose without causing phytotoxicity to field cultivated crops such as corn, and a herbicidal composition containing the villazonole derivative as an active ingredient It relates to the agent.
  • Background art a pyrazole derivative capable of controlling a wide range of field weeds at a low dose without causing phytotoxicity to field cultivated crops such as corn, and a herbicidal composition containing the villazonole derivative as an active ingredient It relates to the agent.
  • Herbicides are extremely important for labor saving in weed control and for improving the productivity of agricultural and horticultural crops.Therefore, research and development of herbicides has been actively carried out for many years, and a wide variety of chemicals are currently in practical use. ing. However, even today, there is a demand for the development of new drugs that have more excellent herbicidal properties, especially those that can control only the target weeds selectively and at a low dose without causing phytotoxicity to cultivated crops. ing.
  • Atrazine which is a triazine herbicide, and alarachlor (a 1 achlor) and metolachlor (me tolachlor), which are acid-based herbicides
  • Atrazine has a low activity against grass weeds, and aclarol and metolachlor have low activities against broadleaf weeds. Therefore, it is currently difficult to control gramineous and broadleaf weeds at once with a single agent.
  • these herbicides require high doses and are not preferred on environmental issues.
  • the present invention provides a novel compound capable of controlling a wide range of field weeds at a low dose without causing phytotoxicity to field-cultivated crops such as corn under such a circumstance. It is intended to provide high-performance herbicides for agricultural or non-agricultural use.
  • the present inventors have conducted intensive studies to achieve the above object, and as a result, have found that a pyrazole-based compound having a specific structure can achieve the object.
  • the present invention has been completed based on this finding. That is, the present invention provides a compound represented by the general formula (I)
  • X is an oxygen atom
  • z is an oxygen atom or formula
  • Z is represented by the formula 1 0— S— or 1 S— 0—
  • o 2 0 is not a group represented by 2.
  • R 36 The group represented by R 36 is shown.
  • X is an oxygen atom or a group represented by the formula
  • Q is a substituted or unsubstituted naphthyl group, which is condensed or not condensed with a benzene ring, which may be interrupted by one or two oxygen atoms and Z or a sulfur atom, substituted or unsubstituted cycloalkyl group C 3 -C 6 of, C 4 cycloalkenyl group ⁇ c 6 containing or oxygen, the heteroatom one to three pieces selected from among nitrogen and sulfur atoms, becomes condensed with a benzene ring or A substituted or unsubstituted 5- or 6-membered aromatic heterocyclic group, which is not fused, and an ethylene oxide group which may be substituted with a C i -C 4 alkyl group.
  • the sulfur atom contained in the cycloalkyl and cycloalkenyl groups may be partially or completely oxidized by oxygen.
  • R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a Ci C alkyl group or a C i -C 4 alkyl group.
  • R 3 may be interrupted by a hydrogen atom, one or two oxygen atoms and a hydrogen atom or a sulfur atom, and may have a halogen atom.
  • R 4 is a hydrogen atom, one or two oxygen atoms and Roh or may be interrupted by a sulfur atom, also good Ci Cs-chain alkyl group which may have a halogen atom, there Rere is C 2 ⁇ A C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a cyano group, a carboxyl group or a (Ci-C 4 alkoxy) carbonyl group; Partially or fully oxidized
  • R 5 is a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and or sulfur atoms which may be interrupted by, also have may ⁇ 1 ⁇ a halogen atom 6 chain Arukiru Group or.
  • R 6 is a halogen atom, a nitro group, one or two oxygen atoms and Roh or sulfur atom may be interrupted by, also have good Ci Ce-chain alkyl group or a C 3 be ⁇ a halogen atom C 6 cyclic alkyl group or a carboxyl group, Shiano group, Chioshiano groups, C alkoxyl group, Ji ⁇ Ji haloalkoxyl group, ( ⁇ -C 4 alkoxy) carbonyl group, a mercapto groups, C alkylthio group,
  • the sulfur atom contained in the -C 6 chain alkyl group or the C 3 -C 6 cyclic alkyl group may be partially or completely oxidized by oxygen.
  • Xi X 7 represents an oxygen atom or a sulfur atom, respectively.
  • R 7 and R 8 may be each independently interrupted by a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and / or sulfur atoms, and have a halogen atom.
  • R 1G may be interrupted by a hydrogen atom, one or two oxygen atoms and Z or sulfur atom, and may have a halogen atom.
  • R 11 and R 12 are each independently a hydrogen atom, a nitro group, a carboxyl group, shea Anomoto, C -C 4 alkyl group, C i ⁇ C 4 haloalkyl group, (Ji-Ji alkoxy) carbonyl group or one Indicates COR 39 .
  • R 13 represents a hydrogen atom, a C Ce alkyl group, ⁇ to ⁇ , an alkyl group or a substituted or unsubstituted phenyl group.
  • R 14 is a hydrogen atom, a halogen atom,. ⁇ ⁇ alkyl group or. ⁇ represents a haloalkyl group.
  • R 15 to R 23 , R 26 and R 27 are each a hydrogen atom, a halogen atom,. ⁇ represents an alkyl group or C ⁇ or an alkyl group.
  • R 24 and R 25 are each a hydrogen atom, a halogen atom, Ci ⁇ C 4 alkyl groups, C I ⁇ C 4 haloalkyl groups, C i C Anorekokishiru groups, C ⁇ Ji haloalkoxyl group, a carboxyl group, (C 1 - C 4 anoreoxy) carbonyl group, C 1 -C 4 alkylthio group, and so on. It represents an alkylsulfiel group, a C i -C 4 alkylsulfonyl group, an amino group, a mono (CC alkyl) amino group or a di (di-alkyl) amino group.
  • R 28 , shaku 29 and shaku 31 ⁇ ! 3 ⁇ 4 34 are each a hydrogen atom, a halogen atom,
  • R 35 and R 36 each independently represent a hydrogen atom, a halogen atom, a CiC alkyl group, a C i -C 4 haloalkyl group, a C alkoxyl group, or R 3
  • R 30 , R 37 , R 38 and R 4G each represent a hydrogen atom or an alkyl group.
  • ⁇ represents an alkyl group or a substituted or unsubstituted phenyl group.
  • k represents the length of the methylene chain and is 0, 1 or 2.
  • n 0 or 1.
  • m, p and q each represent 0, 1 or 2, when p is 2, two R 24 of N RI may be the same or different, and when q is 2, two R 6 Each of which may be the same or different).
  • the present invention also provides a herbicide containing the pyrazole derivative and Z or a salt thereof as an active ingredient.
  • the pyrazole derivative of the present invention has the general formula (I) It is a compound represented by these.
  • X is an oxygen atom or a formula ⁇
  • ' ⁇ 29' indicates the group represented by '29, but when Y represents an asymmetric group, the bond on the left is bonded to the X part and the bond on the right is bonded to the Z part.
  • Z is an oxygen atom, or the formula
  • -N— represents a group represented by C-, but when Z represents an asymmetric group, the bond on the left T is connected to the zen ring, and the bond on the right is connected to the Y part
  • R is a group represented by R 29,
  • 0 is not a 2 0 2 in a group represented by.
  • X is an oxygen atom or a group represented by the formula
  • Represents a group represented by Q is a substituted or unsubstituted naphthyl group, which is condensed or not condensed with a benzene ring, which may be interrupted by one or two oxygen atoms and / or sulfur atoms, C 3 -C cycloalkyl group 6, C 4 ⁇ cycloalkenyl group C 6 or oxygen, nitrogen and a heteroatom 1-3 pieces selected from among sulfur atom, formed by condensation with a benzene ring or fused, and it has not substituted or unsubstituted 5-membered or 6-membered aromatic heterocyclic group, yet represents a C 1 -C 4 7 alkyl optionally Echirenokishido group optionally substituted with a group.
  • the sulfur atom contained in the cycloalkyl and cycloalkenyl groups may be partially or completely oxidized by oxygen.
  • a cycloalkyl group or Shikuroaruke two Le group substituents of C 4 -C 6 of C 3 -C 6 examples include a halogen atom, a nitro group, a carboxyl group, Shiano group, CC alkyl group, C to C, mouth alkyl group,
  • Two groups can be mentioned preferably.
  • the C 3 -C 6 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • Examples of the C 4 -C 6 cycloalkenyl group include a cyclobutyl group, a cyclopentenyl group, Xenyl group.
  • Examples of the C 3 to C 6 cycloalkyl group and the C 4 to C 6 cycloalkyl group condensed with a benzene ring include those obtained by condensing a benzene ring with each of the groups exemplified above.
  • the sulfur atom contained in each of the above structures may be partially oxidized by oxygen to be a sulfoxide (S ⁇ ) or completely oxidized to be a sulfone (S ⁇ 2 ).
  • Examples of a benzene ring fused with one composed or two oxygen atoms and / or cycloalkyl group optionally C 3 -C 6 also therefore be interrupted by a sulfur atom, Shikuroa alkenyl group of C 4 -C 6 and Preferably,
  • the sulfur atom contained in each of the above structures may be partially oxidized by oxygen to be a sulfoxide (so) or completely oxidized to be a sulfone (so 2 ).
  • the 5- or 6-membered aromatic heterocyclic group not condensed with the benzene ring has a substituent on the ring, or the 5- or 6-membered aromatic group condensed with the benzene ring
  • examples of such a substituent include a halogen atom, a cyano group, a nitro group, a carboxy group, a hydroxy group, a hydroxy group, an amino group, Mono (C i C alkyl) amino group, di (C i -C 4 alkyl) amino group, ⁇ ⁇ .
  • Alkyl groups, C I ⁇ C, mouth alkyl groups, C alkoxyl groups, C i C ⁇ Roarukokishiru group, (Ji ⁇ . Alkyl) force carbonyl group, (. ⁇ Ji alkoxy) carbonyl groups, C I ⁇ C 4 alkylthio groups mention may be made preferably from 1 to 3 groups selected from among C alkylsulfinyl group and Ci ⁇ c 4 alkylsulfonyl group.
  • 5-membered aromatic heterocyclic groups not containing a benzene ring and containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur atoms include furan, thiophene thiophene), pyrrole (pyrrole), oxazonole (oxazole), thiazonole (thiazole), imidazonole (imidazole) Residues such as thiadiazole and triazole are listed.
  • Examples of a 6-membered aromatic heterocyclic group which does not condense with a benzene ring and has 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur atoms include pyridine (.pyridine), Residues such as biligcine (pyridazine, pyrimidine (.pyrimidine), pyrazine (prazine), triazine (triazine), oxaziazine (oxadiazine), and thiaziazine (thiadiazine) are included, while oxygen, nitrogen and sulfur atoms are included.
  • Examples of a 5- or 6-membered aromatic heterocyclic group condensed with a benzene ring containing 1 to 3 heteroatoms selected from benzofliran, benzothiophene, and indone Indole
  • benzoxazole benzothiazole (benzothiazole), benzimidazono (benzimidazole), benzoisothiazole (benzoisothiazole), indazoino
  • indazole (indazole), benzothiadiazole, quinoline, quinoline, isoquinoline, cinnoline, phthalazine, phthalazine, quinazoline, and quinoxaline.
  • Preferred examples of the 5- or 6-membered aromatic heterocyclic group not condensed with the benzene ring include furan, thiophene, oxazole, thiazole, isoxazole, isothiazole, pyridine, pyrimidine and triazine residues. More preferred are furan, thiophene, thiazole, isoxazole and pyridine residues, and particularly preferred are thiophene and pyridine residues.
  • preferred 5- or 6-membered aromatic heterocyclic groups fused to a benzene ring include benzothiophene, benzoxazonole and benzothiazonole residues.
  • substituents bonded on the ring of the 5- or 6-membered aromatic heterocyclic group not condensed with a benzene ring, or 5- or 6-membered aromaticity condensed with a benzene ring Preferred examples of the substituent bonded to the benzene ring and Z or the heterocyclic ring of the tetracyclic group include a halogen atom, a carboxyl group, a C i -C 4 alkyl group, a C -dialkyl group and a dialkyl group. , C alkoxyl group and
  • C 4 alkoxy) carbonyl group more preferably, a nitrogen atom, an alkyl group, a C i C ⁇ opening alkyl group and a (C i C alkoxy) carbonyl group.
  • R 1 ⁇ 1 and 13 ⁇ 4 2 each independently represent a hydrogen atom, Ji 1 ⁇ 4 Arukiru group or ⁇ 1 ⁇ 4 haloalkyl group.
  • Preferred examples of R 1 and R 2 include a hydrogen atom and a Ci C alkyl group, and particularly preferred are a hydrogen atom and a methyl group.
  • R 3 may be interrupted by a hydrogen atom, one or two oxygen atoms and / or sulfur atoms, and may have a halogen atom.
  • R 3 preferred are a hydrogen atom, one or two oxygen atoms and a C 6 -C 6 alkyl group which may be interrupted by a hydrogen atom or a sulfur atom, C 1 -C 4, Examples thereof include an alkyl group and a C 3 to C 6 cycloalkyl group. More preferable examples include a hydrogen atom and a C 4 to C 4 alkyl group. Particularly preferable examples include a methyl group, an ethyl group and An isopropyl group can be mentioned.
  • R 4 may be interrupted by a hydrogen atom, one or two oxygen atoms and / or sulfur atoms, and may have a halogen atom.
  • Ci C 6 chain alkyl group, or C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 Arukini group indicates Shiano group, a carboxyl group or a (Ji ⁇ . alkoxy) carbonylation group, the sulfur atom is partially or by oxygen It may be completely oxidized.
  • R 4 preferred are a C 6 to C 6 alkyl group which may be interrupted by a hydrogen atom, one or two oxygen atoms and / or a sulfur atom, Examples include C i Ce haloalkyl groups and C 3 -C 6 cycloalkyl groups, and further include carboxyl groups and (di-alkoxy) carbonyl groups, and more preferred are a hydrogen atom and a Ci C alkyl group. And particularly preferred are a hydrogen atom and a methyl group.
  • R 5 is a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and
  • It may be interrupted by Z or sulfur atom, and may have halogen atom
  • R 5 preferred are a halogen atom, a nitro group, one or two oxygen atoms and / or an optionally interrupted Ci C
  • R 6 is a halogen atom, a nitro group, one or two oxygen atoms and / or sulfur atom may be interrupted by, also have good Ci Cs-chain alkyl group or a C 3 be ⁇ a halogen atom C 6 cyclic alkyl group, or carboxyl group, cyano group, thiocyano group, C alkoxyl group, C to C 4 haloalkoxyl group,
  • halogen atom a nitro group, CJ ⁇ C 4 alkyl group, C t ⁇ C 4 C port alkyl and C!
  • C 4 alkylsulfonyl group more preferably, halogen atom, nitro group and. ⁇ .
  • Alkyl groups can be mentioned, and particularly preferred are di- to alkyl groups. Most preferred are methyl groups.
  • Xi ⁇ X 7 is independently an oxygen atom or a sulfur atom, are preferred oxygen atoms.
  • Shaku 7 and! 8 each may be independently interrupted by a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and a Z or sulfur atom, and have a halogen atom.
  • examples of the substituent include a halogen atom, a nitro group, a carboxyl group, a cyano group, a CiCT alkyl group, a C ⁇ Alkyl group, C i C alkoxyl group,. 1 ⁇ 4 Haroa Norekokishiru group, (Ci ⁇ C 4 alkoxy) carbonyl group, an alkylthio group,
  • One or two groups selected from a C 4 -C 4 alkylsulfinyl group and a C 4 -C 4 alkylsulfonyl group are preferred.
  • a preferable one is a hydrogen atom, Two oxygen atoms and Roh or may be interrupted by a sulfur atom C i ⁇ C 6 alkyl Le group Ya C 1 -C 6 haloalkyl group, more Ci C alkoxyl group, the.
  • a OCOR 39, one ⁇ _C_ ⁇ 2 R 37, - OC_ ⁇ _NR 13 R 14, -OCHR 37 CN, one OChr 37 C_ ⁇ R 39, one OCHR 37 C0 2 R 38, can be a group represented by one ⁇ _CHR 37 CONR 13 R 14, as preferred Ri yo is Ci Ce alkyl group which may be interrupted by hydrogen atom, 1 or 2 oxygen atoms and / or sulfur atoms, and Ci to C 4 alkoxy groups and C 1 to C and lower alkoxyl groups Particularly preferred are a hydrogen atom, a CiC alkyl group and a CiC alkoxyl group, and most preferred are a hydrogen atom, a methyl group and a methoxy group.
  • R 9 is a hydrogen atom, C Cs alkyl group, C -C 6 haloalkyl group, - shows a COR 39 or over 3_Rei 2 1 39.
  • R 9 preferred are a hydrogen atom and a Ci Ce alkyl group, and more preferred are a hydrogen atom, a methyl group and an ethyl group.
  • R 1Q may be interrupted by a hydrogen atom, one or two oxygen atoms and / or sulfur atoms, and may have a halogen atom.
  • R 1 like this.
  • C 2 -C 6 can be cited Haroaruke alkenyl group and C 2 -C 6 alkynyl group, more preferred are a hydrogen atom, and CC alkyl group.
  • R 11 and R 12 are each independently a hydrogen atom, a nitro group, a carboxyl group, shea Anomoto, alkyl group, Ji ⁇ port alkyl group, a ( ⁇ Ji alkoxy) carbonyl group or one COR 39.
  • R 11 and R 12 preferred is a hydrogen atom.
  • Anorekinore group can be exemplified ⁇ 1 ⁇ 4 C port alkyl and (CC alkoxy) carbonyl group, as more preferable, a hydrogen atom and. And 4 alkyl groups.
  • R 13 is a hydrogen atom, a Ci Cs alkyl group, -Represents a haloalkyl group or a substituted or unsubstituted fluoro group.
  • phenyl group is a substituent
  • substituent for example, a halogen atom, a nitro group, a carboxyl group, Shiano group, Ci C alkyl group, Ci ⁇ C 4 haloalkyl group, CC alkoxy group, Ci C haloalkoxyl group , (Ci
  • C alkylthio group preferably one or two groups selected from among Ci ⁇ C 4 alkyl sulfinyl group and C alkylsulfonyl group.
  • a hydrogen atom, a C Ce alkyl group, or a halogen atom, a C 1 to C 4 alkyl group and a C 1 to C 4 alkoxyl group are preferable.
  • examples thereof include a phenyl group which may be substituted with a group, and more preferable examples include a hydrogen atom and a CiC alkyl group.
  • R 14 represents a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group.
  • R 14 include a hydrogen atom and an alkyl group, and more preferred examples include a hydrogen atom and a methyl group.
  • R 15 to R 23 , R 26 and R 27 each represent a hydrogen atom, a halogen atom, a Ci C alkyl group or a C 1 to C 4 alkyl group.
  • a hydrogen atom can be a halogen atom and Ci ⁇ C 4 alkyl group, more preferred are an be mentioned hydrogen atom, a chlorine atom and a methyl group Wear.
  • R 24 and R 25 each represent a hydrogen atom, a halogen atom, a CL to C 4 alkyl group, a C i to C 4 haloalkyl group, a ⁇ to ⁇ ⁇ ⁇ ⁇ alkoxyl group, a C i to C 4 haloalkoxyl group ⁇ / boxyl group, ( shown ci C alkoxy) carbonyl group, Ci C alkylthio group, C ⁇ ⁇ 4 alkylsulfide El group, C I ⁇ C 4 alkylsulfonyl group, amino group, a mono ( ⁇ . alkyl) amino group or a di alkyl) amino group .
  • R 24 and R 25 preferred are a hydrogen atom, a halogen atom, an alkyl group, It can be exemplified haloalkyl groups and Ci ⁇ C 4 alkoxyl group, and more preferred are, there may be mentioned a hydrogen atom, a chlorine atom, methylation group and main butoxy group. /
  • R 28 , R 29 and R 31 to R 34 are each a hydrogen atom, a halogen atom,. ⁇ . It represents an alkyl group or C i to C 2, and an alkyl group. Among them, preferred are a hydrogen atom and an alkyl group, and more preferred are a hydrogen atom and a methyl group.
  • R 35 and R 36 are each independently a hydrogen atom, a halogen atom, N RI 'c 4 Al kill groups, C ⁇ , mouth alkyl groups, C 1 -C 4, or R 3 5 illustrates an alkoxyl group, R 36 and the carbon atom to which they are attached, together form the formula:
  • R 35 and R 36 include a hydrogen atom. And an alkyl group, a C i -C 4 alkoxyl group and R 35 , R 36 and the carbon atom to which they are bonded together, having the formula: R 10
  • R 30 , R 37 , R 38 and R 4 each represents a hydrogen atom or a Ci C alkyl group. Of these, preferred are a hydrogen atom, a methyl group and an ethyl group.
  • R 39 represents a C 4 -C 4 alkyl group, a C i -C 4 alkyl group or a substituted or unsubstituted phenyl group.
  • the full alkenyl group has a substituent, is to this substituent include a halogen atom, a nitro group, a carboxyl group, Shiano group, ⁇ ⁇ 4 alkyl group, C I ⁇ C, mouth alkyl group, .
  • an alkoxyl group selected from the group consisting of: an alkoxyl group, a C 1 -C 4 halanolecoxyl group, a (di-alkoxy) carbonyl group, a CC alkylthio group, a C alkylsulfiel group and a C i -C 4 alkylsulfonyl group.
  • Groups can be mentioned preferably.
  • R 39 preferred are a C 1 -C 4 alkyl group, Cj-
  • a C 4 haloalkyl group or a phenyl group which may be substituted with one or two groups selected from a halogen atom, a C 1 -C 4 alkyl group and a CC alkoxyl group, and more preferred. Examples thereof include alkyl groups.
  • C 6 alkyl groups are of the formula: — CH 2 X 8 CH 3 , —CH 2 X 8 CH 2 CH 3 , — CH 2 X 8 CH 2 CH 2 CH 3 , — CH 2 CH 2 X 8 CH 3 , — CH 2 CH 2 X 8 CH 3 , — CH 2 CH 2 X 8 CH 3 , -CH (CH 3 ) X 8 CH 2 CH 3 , -CH 2 X 8 CH (CH 3 ) 2 , —CH 2 X 8 C (CH 3 ) 3 , -CH 2 X 8 CH (CH 2 CH 3 ) 2 , -CH 2 X 8 CH 2 CH 2 X 9 CH 3 , -CH 2 X 8 CH 2 CH 2 X 9 CH 2 CH 3 , One CH 2 X 8 CH 2 CH 2 X 9
  • one or two are interrupted by an oxygen atom and or a sulfur atom, and in the C ⁇ Ji 6 chain alkyl group or a C 3 -C 6 cyclic alkyl group having a halogen atom, C ⁇ C 6 haloalkyl group As the (chain), for example, one or two oxygen atoms and / or one or more hydrogen atoms of a C Ce alkyl group (chain) interrupted by a sulfur atom may be replaced by a halogen atom. Specific examples thereof include those substituted with a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • X 8 and X 9 each represent an oxygen atom or a sulfur atom.
  • they are partially oxidized to sulfoxide (so) or completely oxidized to sulfon (so 2 ). You may.
  • n 0 or 1
  • m, p and q represent 0, 1 or 2, respectively.
  • p 2
  • p 2
  • q 2
  • q 2
  • q 2
  • q 2
  • q 2
  • p and q are each preferably 0 or 1.
  • Preferred among the pyrazole derivatives represented by the general formula (I) are those represented by the general formula (I-a)
  • X is a formula
  • R 28 , R 29 , R 31 and R 32 are as defined above, and Z is a group represented by the formula
  • Such compounds include the general formula (I-b), the general formula (I_c), the general formula (I-d) or the general formula (I-e)
  • the salt is also included in the pyrazole derivative of the present invention.
  • the virazole derivative of the present invention does not cause harm to field cultivated crops such as corn, has excellent herbicidal activity, and can control a wide range of field weeds at a low dose.
  • the pyrazole derivative for example, the compound represented by the general formula (1 ′) in which X 1 in the general formula (I) is an oxygen atom is represented by the following reaction formula
  • Halogen (wherein, Q, 1 ⁇ ⁇ 11 6, X, Y, Z, k and q are same as that defined above) as shown in, pyrazole derivative of the general formula (II) (III) It can be produced by a method of reacting a compound (Method A) and a method of reacting a pyrazole derivative of the general formula (II) with an alcohol of the general formula (IV) (Method B).
  • a virazole derivative of the general formula (II) is reacted with a halogenic compound of the general formula (III) in an inert solvent in the presence of a hydrogen halide scavenger to obtain a compound of the general formula A compound represented by (I ') is produced.
  • the halogen compound of the general formula (II) is preferably used in a proportion of generally 1 to 3 mol per 1 mol of the virazole derivative of the general formula (II).
  • the hydrogen halide scavenger for example, bases such as sodium carbonate, potassium carbonate, triethylamine and pyridine are used.
  • These hydrogen halide scavengers are preferably used in an equimolar ratio or more with respect to the compound of the general formula (II), and the reaction temperature is preferably in a range from room temperature to the boiling point of the solvent used.
  • the inert solvent include aromatic hydrocarbons such as benzene and toluene, ethers such as getyl ether, ketones such as methylethyl ketone, and halogenated hydrocarbons such as dichloromethane, chlorohonolem, and dichloroethane.
  • azodicarboxylic acid diester By reacting the pyrazole derivative of the general formula (II) with the alcohol of the general formula (IV) in the presence of a dehydrating condensing agent such as triffeine phosphine, the compound represented by the general formula () is produced. .
  • the alcohol of the general formula (IV) is preferably used in a proportion of generally 1 to 2 mol per 1 mol of the birazol derivative of the general formula (II).
  • the reaction temperature is preferably in the range from room temperature to the boiling point of the solvent used.
  • the inert solvent examples include, for example, aromatic hydrocarbons such as benzene and toluene, ethers such as jetinole ether, halogenated hydrocarbons such as dichloromethane, chloropho / rem, and dichloroethane.
  • the Lawesson reagent is generally preferably used in an amount of 0.5 to 1 mol based on the pyrazonole derivative (I ').
  • the reaction temperature is preferably in the range from room temperature to the boiling point of the solvent used.
  • the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, and ethers such as dimethyl ether and dimethoxyethane.
  • the pyrazole derivative represented by the general formula (II) can be prepared by a known method (for example, WO93 / 18031, WO94 / 01431, WO95 / 4054, W096 / 25412, W095 / 13275,
  • the herbicide of the present invention contains the pyrazole derivative of the present invention represented by the general formula (I) and / or a salt thereof as an active ingredient, and comprises a compound such as a liquid carrier such as a solvent or a fine powder of a mineral substance. It can be used in the form of a wettable powder, emulsion, powder, granule, etc. by mixing with a solid carrier such as In order to provide emulsifying, dispersing and spreading properties during formulation, a surfactant must be added.
  • the pyrazole derivative of the present invention and Z or a salt thereof are usually 10 to 55% by weight, and the solid carrier is 40 to 88% by weight. /.
  • a surfactant may be blended at a ratio of 2 to 5% by weight to prepare a composition, which may be used.
  • the pyrazole derivative of the present invention and / or a salt thereof is usually contained in an amount of 20 to 50% by weight, a solid carrier of 35 to 75% by weight, and a surfactant of 5 to 15% by weight. What is necessary is just to mix
  • the pyrazole derivative of the present invention and / or a salt thereof when used in the form of a powder, is usually 1 to 15% by weight. / 0 , a solid carrier may be blended at a ratio of 80 to 97% by weight and a surfactant at a ratio of 2 to 5% by weight to prepare a composition. Further, when used in the form of granules, usually the proportion of the pyrazole derivative of the present invention and / or its salt is 1 to 15% by weight, the solid carrier is 80 to 97% by weight, and the surfactant is 2 to 5% by weight. To prepare a composition. Here, a fine powder of a mineral substance is used as the solid carrier.
  • Examples of the fine powder of the mineral substance include oxides such as kieselguhr, slaked lime, phosphates such as apatite, sulfates such as Secco, tanolek, Pai mouth ferrite, clay, kaolin, bentonite, acid clay, white carbon, quartz powder, and silicates such as calcium stone powder.
  • oxides such as kieselguhr, slaked lime, phosphates such as apatite, sulfates such as Secco, tanolek, Pai mouth ferrite, clay, kaolin, bentonite, acid clay, white carbon, quartz powder, and silicates such as calcium stone powder.
  • Organic solvents are used as the solvent.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • chlorinated hydrocarbons such as 0-chlorotoluene, trichloroethane and trichloroethylene
  • cyclohexanol Amanol alcohol, ethylene glycolone, etc., ketones, such as isophorone, cyclohexanone, cyclohexeninole-cyclohexanone, buty celsburgoleb
  • ethers such as jeti / letenoleno, methylinoethyl ether, isopropyl acetate, benzyl acetate, phthalic acid
  • esters such as methyl, amides such as dimethylformamide, and mixtures thereof.
  • anionic type fatty acid salt, alkylsulfate, anolequinolebenzenesnolephonic acid, dianolequinolenesolephosuccinate, anolequinolephosphate phosphate, naphthalene sulfone
  • anionic type fatty acid salt, alkylsulfate, anolequinolebenzenesnolephonic acid, dianolequinolenesolephosuccinate, anolequinolephosphate phosphate, naphthalene sulfone
  • nonion type polyoxyethylene alkyl enoate, polyoxyethylene anolequinole pheninoleate enole, polyoxyethylene anolequinoleester
  • cationic or amphoteric ion type amino acid, betaine, etc.
  • the herbicide of the present invention may contain, if necessary, other herbicidal active ingredients, together with the pyrazole derivative represented by the above general formula (I), and / or its salt.
  • Such other herbicidally active ingredients include conventionally known herbicides such as phenoxy, diphenyl ether, triazine, urea, carbamate, thiol carbamate, acid anilide, pyrazole, phosphoric acid System, sulfonylurea system, oxaziazone system, etc., and can be used by appropriately selecting from these herbicides.
  • the herbicide of the present invention can be mixed with an insecticide, a bactericide, a plant growth regulator, a fertilizer, and the like, if necessary.
  • the herbicide of the present invention is used as a herbicide for upland fields, such as soil treatment, soil mixing treatment, foliage treatment It can be used in any processing method.
  • the field weeds (Cropland weeds) targeted by the compound of the present invention for example, Solanaceae weeds, Abutilon theophrasti, and Amebia typified by, for example, Solanum nigrum, Datura stramonium and the like.
  • Convolvulaceae weeds represented by Malvaceae weeds such as Sika spin deer (Sida spinosa), Asagao species (Ipomoea spps.) Such as Malva Asagao (Ipomoea purpurea), and Convolvulaceae represented by Convolvulus (Calystegia spps.).
  • Amaranthus lividus, etc. Amaranth ace ae, Xanthium strum arium j, Ambrosia artemisiaefolia, Helianthus annus, Gakida cecilia Asteraceae (Compositae) typified by irrigation thistle (Cirsium arvense), Novo-mouth chrysanthemum (Senecio vulgaris), and shrimps (Erigeron annus) ) Weeds, Rorippa indica, Sinapis arvensis, Brassica (Capsellaurea bursa—pastoris) and other cruciferaceae (Cruciferae) weeds. Polygonaceae (Polygonaceae) weeds, Portulaca oleracea (Portulaca oleracea), etc.
  • Scrophulariaceae weeds represented by guri (Veronica persica), etc. Weedes, and communis (Commelina communis), etc.
  • Weeds Broad-leaved weeds such as legumes (Le uminosae) weeds, such as Sesbania exaltata and Cassia obtusifolia, wild sorghum (Sorgham bicolor), ooo Wedge mill (panicum dichotomiflorum), John Songhus (Sorghum
  • the compound of the present invention can be used as a herbicide for paddy fields in any of soil treatment and foliage treatment under flooding.
  • paddy weeds include paddy weeds, such as Herodamodaka (Alisma canaliculatum), Omodaka (Sagittaria trifolia), and Perica (Sagittaria pygmaea).
  • the effective application amount of the compound of the present invention for weeding can be determined in consideration of various conditions such as the form of the preparation, the application method, the type and amount of the weeds, and the growth condition. Usually, it is 0.001 to 0.3 kg / ha, preferably 0.01 to 0.3 kg / ha, and those skilled in the art can easily determine the effective amount for obtaining the required herbicidal effect.
  • talc as a carrier
  • alkylaryl sulfonate as a surfactant
  • Neoperex manufactured by Kao Atlas Co., Ltd.
  • nonionic and anionic surfactants (Sonorepol 80 OA, manufactured by Toho Chemical Industry Co., Ltd.) were uniformly pulverized and mixed to obtain a wettable powder carrier.
  • this carrier for wettable powders 90 parts by weight of this carrier for wettable powders and 10 parts by weight of the compound of the present invention were uniformly ground and mixed to obtain herbicides.
  • the following compounds (A), (B) and (C) were used and prepared in the same manner.
  • the virazole derivative of the present invention does not cause phytotoxicity to field cultivated crops such as corn and can selectively control a wide range of field weeds such as grasses and broadleaf weeds at a low dose.
  • the herbicide of the present invention containing this pyrazole derivative has high performance and is useful not only for agricultural use for controlling upland weeds, but also for non-agricultural use for controlling weeds on non-agricultural lands. is there.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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Abstract

L'invention porte sur des herbicides contenant comme ingrédients actifs des dérivés de pyrazole de la formule générale (I) et/ou des sels de ceux-ci. (Dans cette formule, chaque symbole est tel que défini dans la demande). Les dérivés de pyrazole et leurs sels n'endommagent pas chimiquement les cultures de haute terre telles que le maïs et peuvent éliminer une grande variétés de mauvaises herbes, même à faible dose.
PCT/JP2001/003232 2000-04-19 2001-04-16 Derives de pyrazole et herbicides les contenant WO2001079200A1 (fr)

Priority Applications (1)

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AU46920/01A AU4692001A (en) 2000-04-19 2001-04-16 Pyrazole derivatives and herbicides containing the same

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JP2000-118112 2000-04-19
JP2000118112 2000-04-19

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995004054A1 (fr) * 1993-08-02 1995-02-09 Idemitsu Kosan Co., Ltd. Derive de pyrazole
WO1995013275A1 (fr) * 1993-11-09 1995-05-18 Idemitsu Kosan Co., Ltd. Derives de pyrazole et herbicide les contenant
WO1996000008A1 (fr) * 1994-06-27 1996-01-04 Idemitsu Kosan Co., Ltd. Composition herbicide
WO1996030368A1 (fr) * 1995-03-28 1996-10-03 Idemitsu Kosan Co., Ltd. Derives de pyrazole
WO1996031507A1 (fr) * 1995-04-05 1996-10-10 Idemitsu Kosan Co., Ltd. Derives de pyrazole
WO1997008164A1 (fr) * 1995-08-25 1997-03-06 E.I. Du Pont De Nemours And Company Herbicides bicycliques
WO1997012885A1 (fr) * 1995-10-04 1997-04-10 Idemitsu Kosan Co., Ltd. Derives de pyrazole
WO1997019087A1 (fr) * 1995-11-17 1997-05-29 E.I. Du Pont De Nemours And Company Heterocycles herbicides tricycliques
WO1997023135A1 (fr) * 1995-12-25 1997-07-03 Idemitsu Kosan Co., Ltd. Composition herbicide
EP0810226A1 (fr) * 1995-02-13 1997-12-03 Idemitsu Kosan Company Limited Derives de pyrazole
WO1998049159A1 (fr) * 1997-04-25 1998-11-05 E.I. Du Pont De Nemours And Company Pyrazoles herbicides

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995004054A1 (fr) * 1993-08-02 1995-02-09 Idemitsu Kosan Co., Ltd. Derive de pyrazole
WO1995013275A1 (fr) * 1993-11-09 1995-05-18 Idemitsu Kosan Co., Ltd. Derives de pyrazole et herbicide les contenant
WO1996000008A1 (fr) * 1994-06-27 1996-01-04 Idemitsu Kosan Co., Ltd. Composition herbicide
EP0810226A1 (fr) * 1995-02-13 1997-12-03 Idemitsu Kosan Company Limited Derives de pyrazole
WO1996030368A1 (fr) * 1995-03-28 1996-10-03 Idemitsu Kosan Co., Ltd. Derives de pyrazole
WO1996031507A1 (fr) * 1995-04-05 1996-10-10 Idemitsu Kosan Co., Ltd. Derives de pyrazole
WO1997008164A1 (fr) * 1995-08-25 1997-03-06 E.I. Du Pont De Nemours And Company Herbicides bicycliques
WO1997012885A1 (fr) * 1995-10-04 1997-04-10 Idemitsu Kosan Co., Ltd. Derives de pyrazole
WO1997019087A1 (fr) * 1995-11-17 1997-05-29 E.I. Du Pont De Nemours And Company Heterocycles herbicides tricycliques
WO1997023135A1 (fr) * 1995-12-25 1997-07-03 Idemitsu Kosan Co., Ltd. Composition herbicide
WO1998049159A1 (fr) * 1997-04-25 1998-11-05 E.I. Du Pont De Nemours And Company Pyrazoles herbicides

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