WO2001068613A1 - Dérivés pyrimidinone et herbicides - Google Patents
Dérivés pyrimidinone et herbicides Download PDFInfo
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- WO2001068613A1 WO2001068613A1 PCT/JP2001/002158 JP0102158W WO0168613A1 WO 2001068613 A1 WO2001068613 A1 WO 2001068613A1 JP 0102158 W JP0102158 W JP 0102158W WO 0168613 A1 WO0168613 A1 WO 0168613A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
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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
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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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
- 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
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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
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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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
- 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
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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
- 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
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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
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- the present invention relates to a novel pyrimidinone derivative and a herbicide containing the same as an active ingredient.
- the present inventors have conducted intensive studies on the herbicidal action of the novel pyrimidinone derivative, and as a result, have found that the following compounds have excellent herbicidal action, and have completed the present invention. That is, the present invention relates to [1] and [6].
- R a is a hydrogen atom, Shiano group, C, - C 4 alkyl group, Shiano C '- C 4 alkyl group, C One C 4 alkoxy C, one C 4 alkyl group, C -!! C 4 alkylthio C one C 4 Al kill group, C 1 ten 4 Ha port alkyl group, C 'one C 4 alkylsulfonyl group, a (C One C i alkyl) carbonyl group or (C One C 4 alkoxy) carbonylation group,
- X is a hydrogen atom, (:! Over Ji ⁇ Arukiru group, CC haloalkyl group, Ji '. - 4 ⁇ Lumpur Kokishi groups, C One C 4 haloalkoxy group, C' one c 4 alkylthio group, c '- c 4 It represents a C alkylamino Roh group, or (C] One C 4 7 alkyl) 2 amino group,, - Al alkylsulfonyl group, an amino group, C!
- Y represents an oxygen atom or a sulfur atom
- Z 1 and Z 2 each independently represents a nitrogen atom or CR b, however, the gas when Z 1 represents a nitrogen atom and Z 2 represents CR b, the gas when Z 1 represents CR b Z 2 Represents a nitrogen atom
- R b is a hydrogen atom, a halogen atom, C, one C 4 alkoxy groups, C, - represents C, Roaruko alkoxy group or Shiano group,
- R 1 and R 2 each independently represent a hydrogen atom or a halogen atom
- R 3 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, an amino group, a formyl group, a carboxyl group group, Shiano methyl groups, C One C 4 alkoxy Kishikaruponiru group, a sulfamoyl group, Chiokarubamoiru group, forces Rubamoiru group,
- R 4 is a hydrogen atom, a halogen atom, a formylamino group, a cyano group, a chlorosulfonyl group, a nitro group, a hydrazino group, a substituted phenyl group, a 1,3-dioxolan-12-yl group, a 1,3-dioxane-12 - I le group, C, one C 8 alkyl groups, C 3 - Ji 8 cyclo alkyl groups, C 2 - C 8 alkenyl groups, C 2 - C s alkynyl groups, C One C 8 haloalkyl groups, C 3 — C 8 halogeno cycloalkyl group, C 2 — C 8 haloalkenyl group, C 2 — C 8 haloalkynyl group, (C!
- R 5 is a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, an amino group, a carboxyl group, a mercapto group, a C 1 -C 4 alkyl group, a C 2 -Cs alkenyl group, a C 2 -C 8 alkynyl group , C, — C ⁇ alkoxy group, C] —C 4 haloalkyl group, C 2 —C 8 alkenyloxy group, c 2 —C 8 alkynyloxy group, 2,3-epoxy-12-methylpropyl group or 2 —Methyl-2-propenyl group,
- R 6 and R 7 each independently represent a hydrogen atom, a halogen atom, a C i -C 6 alkyl group, a cyano group or a C-C 6 haloalkyl group;
- R s and R 9 are each independently hydrogen atom, C, - C 8 alkyl group, C 2 -C 8 7 alkenyl group, C 2- C 8 alkynyl group, C 1 - C s haloalkyl group, C 2-C 8 halo Lucenyl group, c 2 —Cs haloalkynyl group, (c, —c 6 alkyl) carbonyl group,
- R 1 Represents a hydrogen atom, a halogen atom, a C 6 alkyl group, a (C) -C 4 alkoxy) carbonyl group or a (C ⁇ —C alkyl) carbonyl group,
- R 1 1 is hydrogen atom, formyl group, carboxyl group, arsenate Dorokishimechiru group, C, one C 6 alkyl group, C, over C 6 haloalkyl group, (0, - 6 Arukiru) carbonyl group, C, - C 4 alkoxy C, one C 4 alkyl group, C one C 4 alkylthio C -!! C 4 Al kill group, C! — C 4 alkyl sulfonyl C! One C 4 alkyl group, (C -! C an alkoxy) Karuponiru group, (C -!
- C alkyl) ⁇ Mi Bruno carbonyl group
- C 3 - C 8 cycloalkyl Lou CH (0 H) or - represents (C 3 C s cycloalkyl) carbonylation group
- R 1 2 is hydrogen atom, halogen atom, amino groups, C -! C 6 alkyl group, one C 6 Nono port alkyl groups, C -! C 6 alkoxy groups, C One C 6 alkylthio group or a C, - C 4 represents an alkoxy (C, — C 4 ) alkyl group,
- R 13 represents a hydrogen atom, a C] -C 6 alkyl group or a substituted phenyl group
- R 14 and R 15 each independently represent a hydrogen atom or a C, -C 6 alkyl group
- R 16 represents a hydrogen atom or a C 1, 1 C 6 alkyl group
- R 17 , R 18 , R 19 and R 2 ° each independently represent a hydrogen atom or (:) one C 6 alkyl group;
- R 21 is a hydrogen atom, a C, —C 6 alkyl group, a (C′—C 6 alkyl) carbonyl group, a (C) —C 6 haloalkyl) carbonyl group, a (C! — C 6 alkoxy) carbonyl group
- R 22 represents a hydrogen atom, a C′—C 6 alkyl group, a C] 1 C 4 haloalkyl group, a hydroxy c) 1 c 4 alkyl group or a c] 1 c 4 alkoxy C, 1 c 4 alkyl group,
- R 3 It is hydrogen, C One C 8 alkyl group, C 3 - C s cycloalkyl, C 2 - C 8 alkenyl, C 2 - C 8 alkynyl group, C 3 - C 8 cycloalkyl d-C alkyl le radical , C′-C 8 haloalkyl group, C 2 -C 8 haloalkenyl group, — (: 8- hydroxyalkynyl group, 4-butanolido-2-yl group, 5-pentanolide-12-yl group , Kisano to 6 Li de one 2-I le group, (d- ⁇ alkoxy) carbonyl group, (C -!
- R 31 is a hydrogen atom, C] - C 8 alkyl group, C 2 - C s alkenyl group, C 2 - C 8 Al Kiniru group, C 3 _ C 8 cycloalkyl group, C 3 - C 8 cycloalkyl C! - C 4 alkyl group, C′-C 6 haloalkyl group, C i-C 4 alkoxy C′-alkyl group, oxetane 13-yl group, C′-C 4 alkylamino group, (C!
- R 32 is a hydrogen atom, one C 8 alkyl group, C 2 - C 8 alkenyl, C 2 - C 8 alkynyl group, C 3 - C 8 cycloalkyl group, or C, - Represents the C 6 haloalkyl group, provided that, R 31 and R 32 may be replaced with a C′-C ⁇ alkyl group together with the bonding nitrogen atom, and may represent a 3- to 8-membered heterocyclic ring.
- the constituents of the ring are optionally selected from carbon, oxygen, sulfur and nitrogen atoms;
- 3 3 ii represents a C> -C 4 alkyl group or a C] 1 C 4 haloalkyl group
- R 34 is a CC s alkyl group, a C 1, 1 C 4 haloalkyl group, a C 3 -C 8 cycloalkyl Group, c 2 - c 8 alkenyl, c 2 - c 8 alkynyl group, a benzyl group or a phenylene group,
- R 35 is a C! —C 8 alkyl group, C 2 —Cs alkenyl group, C 2 —C 8 alkynyl group, C] c 4 haloalkyl group, C 2 — c 8 haloalkenyl group, c 2 — c 8 halo Alkynyl group, cyano C c alkyl group, c] one c 4 alkoxy c! —C ⁇ alkyl group, (
- R 36 is C i-C alkyl, C - C alkenyl group, Ji 2 - ⁇ 8 Arukiniru group, c -! C, mouth alkyl group, a substituted phenyl group or substituted phenyl c, - c 6 alkyl group 3 ⁇ 4 ⁇ represents,
- R 37 is C! One C alkyl group or (C) one C 3 alkoxy) carbonyl! Represents a C s alkyl group
- R 38 represents a hydrogen atom, C] - C 6 alkyl group, C 2 - C 8 alkenyl, C 2 - C s al Kiniru group, a C - ⁇ 8 cycloalkyl group or a benzyl group,
- R 39 is C! One C 8 alkyl group, C 2 —C 8 alkenyl group, C 2 —C 8 alkynyl group, (C, — C 6 alkyl) carbonyl group, (C i — C 6 alkoxy) carbonyl group, C, one C 6 alkyl sulfonyl group or a (C '- C 4 alkoxy) 2 represents P (0),
- L represents a C c 6 alkylene chain which may be saturated or unsaturated and which may be substituted by a halogen atom, a cyano group or a (CC 4 alkoxy) carbonyl group;
- Substituted phenyl is halogen atom, Shiano group, two collected by filtration group, amino group, carboxyl group, arsenate Dorokishi group, C, - C 4 alkyl group, C, over alkoxy group, C -! C haloalkyl group, c, - C 4 C port alkoxy groups, C] over C 4 alkylsulfonyl group, (C, - c 4 alkyl) carbonyl group, (!
- One C 4 alkoxy group or a (C One C haloalkoxy C, one C 4 alkoxy) carboxamide alkenyl C, - represents a C 4 alkoxy optionally optionally substituted Fuweniru group by group,
- the optionally substituted 5- to 6-membered hetero ring may be a halogen atom, a cyano group, a nitro group, an amino group, a propyloxyl group, a hydroxy group, a ⁇ alkyl group, a C, —Ci alkoxy group, a C] -C 4 haloalkyl group, C, 1 C 4 haloalkoxy group, C] 1 C 4 alkylsulfonyl group, (C! -C ⁇ alkyl) carbonyl group, (C!
- R a is (: One C 4 alkyl group, Ji ⁇ over Ji Haroarukiru group or ⁇ - represents Ji ⁇ ⁇ Le Kirusuruho two group,
- X represents a hydrogen atom, C] an alkyl group or an amino group
- Y represents an oxygen atom
- Z 1 represents a nitrogen atom
- Z 2 represents CR b
- R b represents a halogen atom
- R 1 represents a hydrogen atom or a fluorine atom
- NHC H2 CO 2C H 2P h NHCHM e C_ ⁇ 2 M e, NHCHMe C0 2 E t, N hCHM e C0 2 P r, NHCHMe C0 2 (iso- P r), hCHM e CO 2 P en, NHC HM e C 0 2 (eye 1 0- P en), NHC0 2 Me, NHC 0 2 E t, NHC 0 2 P r, NH C 02 (iso- P r), NHC0 2 B u, NHC 02 (eye 10-Pr), NHC 02 (eye 10-P en), NHC 02 (iso—Bu), NHC 02 (sec—Bu), NHC 02 (tert-Bu) ), NHC 0 2 CH 2 CHCHCH 3, NHC 02 CH 2 CH CH 2, NH CO zC H 2C ⁇ CH, NHC 0 2 P h, NHC 0 2 CH 2 P h, NH C 02C
- the compound of the present invention can be produced by the methods shown in Reaction Schemes 1 to 8.
- Q-and X represents the same meaning as above, a halogen atom H a 1 1 and H a 1 2 each independently. Represents a C 4 C 4 alkyl group.
- Step 1 of the reaction scheme 1 is a part of the compound of the present invention by reacting benzoyl acetic acid (2) with an amidine or a salt thereof (3) in the presence of a base, followed by acid treatment. This is a process for producing a pyrimidinone derivative (la-l).
- (3) is usually used in a molar amount of 1 to 100 times, preferably 1 to 10 times the molar amount of (2).
- Bases include sodium hydride, sodium hydride, sodium methoxide, sodium ethoxide, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide and tetramethyldanidine. Is raised.
- the base is used usually in a molar amount of 1 to 100 times, preferably 1 to 10 times the molar amount of (2).
- the reaction proceeds even without solvent, but a solvent can be used if necessary.
- the solvent is not particularly limited as long as it is inert to the reaction.
- the reaction temperature is usually from 90 to 20 Ot, preferably from 0 to 120 ° C.
- the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours. is there.
- the solvent is distilled off, water is added to the residue, and after acid treatment, the solid is collected by filtration to isolate the desired product.
- the acid used for the acid treatment include hydrochloric acid, sulfuric acid, phosphoric acid, and acetic acid.
- step 2 the pyrimidinone derivative (1a-1) which is a part of the compound of the present invention is reacted by reacting the pyrimidinone derivative (1a-1) with chlorodifluoromethane or ethyl bromodifluoroacetate in the presence of a base. 2).
- Chlorodifluoromethane or ethyl bromodifluoroacetate is generally used in an amount of 1 to 100 times, preferably 1 to 10 times, the mole of (1a-1).
- Bases include sodium hydride, lithium hydride, sodium hydride, sodium methoxide, sodium ethoxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, etc. Is raised.
- the base is usually used in a molar amount of 1 to 100 times, preferably 1 to 10 times, to (la-11). This reaction proceeds even without solvent, but a solvent can be used if necessary.
- the solvent is not particularly limited as long as it is inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dioxane and 1 , 2-dimethoxetane and the like.
- the reaction temperature is usually from 190 to 200 " ⁇ , preferably from 0 to 120.
- the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
- Step 3 is a step of producing a pyrimidinone derivative (la-3) which is a part of the compound of the present invention by reacting the pyrimidinone derivative (1a-2) with a halogenating agent.
- halogenating agent used in this reaction examples include chlorine, bromine, fluorine, iodine, sulfuryl chloride, tert-butyl hypochlorite, N-chlorosuccinic imid, N-bromosuccinic imid and the like. N-odeconodic acid imid.
- the hydrogenating agent is used usually in an amount of 1 to 100 times, preferably 1 to 10 times the mole of (1a-2).
- a catalyst can be added as necessary.
- the catalyst used is salt Cuprous iodide, cupric chloride, cuprous bromide, cupric bromide, cuprous iodide, cupric fluoride and the like.
- the reaction proceeds even without solvent, but a solvent can be used if necessary.
- the solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include chloroform, dichloromethane, methanol, ethanol, and acetonitrile.
- the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
- the reaction time is usually from 0.5 hours to 100 hours, preferably from 0.5 to 10 hours.
- Q-, X, R a ⁇ Pi H a 1 2 represents the same meaning as above, H a 1 3 halo gen atom, C, one C 4 alkylsulfonyl O carboxymethyl, C ⁇ 4 Ha port Represents an alkylsulfonyloxy group or a substituted phenylsulfonyloxy group.
- step 4 of Reaction Scheme 2 the pyrimidinone derivative (la-l) is reacted with an electrophilic reagent (4) in the presence of a base to form a pyrimidinone derivative (1a -4) This is the manufacturing process.
- the base is used usually in a molar amount of 1 to 100 times, preferably 1 to 10 times the molar amount of (1a.-1).
- This reaction proceeds even without solvent, but a solvent can be used if necessary.
- the solvent is not particularly limited as long as it is inert to the reaction. For example, N, N-dimethylforma Mid, N, N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dioxane and 1,2-dimethoxetane.
- the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
- the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
- Step 5 is a step of producing a pyrimidinone derivative (la-5) which is a part of the compound of the present invention by reacting the pyrimidinone derivative (1a-4) with a halogenating agent. This reaction can be carried out in the same manner as in Step 3 of Reaction Scheme 1.
- step 6 of Reaction formula 3 the pyrimidinone derivative (la-6), which is a part of the compound of the present invention, is produced by reacting the pyrimidinone derivative (1a-1) with a halogenating agent. This is the process of manufacturing. This reaction can be carried out in the same manner as in Step 3 of Reaction Scheme 1.
- step 7 the pyrimidinone derivative (1a-6) is reacted with chlorodifluoromethane or ethyl bromodifluoroacetate in the presence of a base to form a pyrimidinone derivative (la-3 ).
- This reaction can be carried out in the same manner as in Step 2 of Reaction Scheme 1.
- Step 8 comprises reacting the pyrimidinone derivative (la-6) with an electrophile (4) in the presence of a base to produce a pyrimidinone derivative (1a-5) which is a part of the compound of the present invention. It is a process. This reaction can be carried out in the same manner as in Step 4 of Reaction Scheme 2. (Reaction formula 4)
- Reaction Scheme 4 is a reaction between a benzoylacetic acid (2) and an amidine or a salt thereof (5) in the presence of a base or an acid to give a pyrimidinone derivative (1a) which is a part of the compound of the present invention. — 4).
- (5) is generally used in a molar amount of 1 to 100 times, preferably 1 to 10 times the molar amount of (2).
- the base used in this reaction is sodium hydride, lithium hydride, potassium hydride, sodium methoxide, sodium ethoxide, sodium carbonate, potassium carbonate, Examples include sodium hydroxide, potassium hydroxide and tetramethylguanidine, and the acid is p-toluenesulfonic acid, acetic acid, propionic acid, trifluoroacetic acid, hydrochloric acid, sulfuric acid, phosphoric acid And methanesulfonic acid and trifluoromethanesulfonic acid.
- the base or acid is generally used in a molar amount of 1 to 100 times, preferably 1 to 10 times the molar amount of (2).
- the reaction proceeds even without solvent, but a solvent can be used if necessary.
- the solvent is not particularly limited as long as it is inert to the reaction.
- Examples include dimethoxetane, methanol, ethanol, isopropanol, benzene, toluene, xylene, acetonitrile, and chloroform.
- the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
- the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
- Reaction formula 5 produces a pyrimidinone derivative (1a-7) which is a part of the compound of the present invention by reacting the acyl imidates (6) with the acetamides (7).
- This reaction can be carried out according to the method described in J. Chem. Soc., PerkinTrans. 1, 2447 (1984).
- Step 9 of Reaction Scheme 6 comprises reacting the pyrimidinone derivative (1a-7) with chlorodifluoromethane or ethyl bromodifluoroacetate in the presence of a base to obtain a pyrimidinone derivative (part of the compound of the present invention). This is the process of manufacturing la-8). This reaction can be carried out in the same manner as in Step 2 of Reaction Scheme 1.
- Step 10 comprises reacting the pyrimidinone derivative (1a-7) with an electrophile (4) in the presence of a base to form a pyrimidinone derivative (la-9) which is a part of the compound of the present invention.
- This reaction can be carried out in the same manner as in Reaction Scheme 2, Step 4. (Reaction formula 7)
- Reaction formula 7 shows that pyrimidinone, a part of the compound of the present invention, is obtained by reacting a monodiketone (8) or a vinyl ketone (9) with a urea (I 0) in the presence of a base or an acid.
- a monodiketone (8) or a vinyl ketone (9) with a urea (I 0) in the presence of a base or an acid.
- the method for producing the derivative (Ib-I) will be described.
- (10) is generally used in a molar amount of 1 to 100 times, preferably 1 to 10 times the molar amount of (8) or (9).
- the base used in this reaction is sodium hydride, lithium hydride, potassium hydride, sodium methoxide, sodium ethoxide, sodium carbonate, potassium carbonate. , Sodium hydroxide, potassium hydroxide and tetramethyldanidine, and the acids include p-toluenesulfonic acid, acetic acid, propionic acid, trifluoroacetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, Tansulfonic acid and trifluoromethansulfonic acid.
- the base or acid is generally used in a molar amount of 1 to 100 times, preferably 1 to 10 times the molar amount of (8) or (9).
- the reaction proceeds even without solvent, but a solvent can be used if necessary.
- the solvent is not particularly limited as long as it is inert to the reaction.
- N N-dimethylformamide
- N : — dimethylacetamide, dimethylsulfoxide, tetrahydrofuran
- Examples include 2-dimethoxetane, methanol, ethanol, isoprono, anol, benzene, toluene, xylene, acetonitrile, and chloroform.
- the reaction temperature is usually from 190 to 200, preferably from 0 to 120 °.
- the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
- Step 11 of Reaction Formula 8 is to react the pyrimidinone derivative (1b-1) with clomouth difluoromethane or ethyl bromodifluoroacetate in the presence of a base to thereby form a pyrimidinone derivative which is a part of the compound of the present invention.
- This is a process for producing derivatives (lb-2). This reaction can be carried out in the same manner as in Step 2 of Reaction Scheme 1.
- a pyrimidinone derivative (lb-3) which is a part of the compound of the present invention is produced by reacting the pyrimidinone derivative (1b-1) with an electrophile (4) in the presence of a base.
- This is the step of performing This reaction can be carried out in the same manner as in Step 4 of Reaction Scheme 2.
- 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.
- Acetamidine hydrochloride (21.5 g) and sodium methoxide (10.2 g) were added to ethanol (250 ml), and the mixture was heated under reflux for 15 minutes. Under ice-cooling, 2,4-difluorobenzoyl acetate ethyl (21.5 g) was added dropwise, and the mixture was refluxed for 2 hours. After evaporating the solvent under reduced pressure, ice water (200 ml) was added to the residue, and 6 N hydrochloric acid was added until the solution became acidic. The obtained solid was collected by filtration, washed with diisopropyl ether, and dried to obtain 13.3 g of the desired product. Above melting point 250.
- Iron powder (2.0 g, acetic acid (10 ml), ethyl acetate (10 ml) and water (30 ml) were added to the obtained residue, and the mixture was heated under reflux for 3 hours. 1) and ethyl acetate (100 ml) were added, and the insolubles were filtered off. The organic layer of the filtrate was separated, washed successively with water and a saturated aqueous solution of sodium hydrogencarbonate, and dried over anhydrous magnesium sulfate. The residue obtained was recrystallized from isopropyl ether to give 1.1 g of the desired product as a colorless solid.
- the ether layer was separated, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off.
- Iron powder (0.086 g) was added to a mixture of ethyl acetate (2 ml), acetic acid (1 ml) and water (2 ml), and the mixture was refluxed with 5-chloro-1-difluoromethyl monohydrate.
- Acetamidine hydrochloride (8.90 g) and sodium methoxide (8.90 g) were added to a solution of 4-bromo-1-fluoro-5-methoxybenzoyl acetate ethyl (20.0 g) in ethanol (400 ml). 8.50 g) was added, and the mixture was refluxed for 6 hours. After the solvent was distilled off, ice water (200 ml) was added to the residue, and 6 hydrochloric acid was added until the solution became acidic. The obtained solid was collected by filtration, washed with getyl ether, and dried to obtain 14.2 g of the desired product. Mp 2997—300 ° C.
- Tables 1 to 3 show the structural formulas and physical properties of the compounds of the present invention synthesized according to the above Examples, including the above Examples. However, the symbols in the table have the same meaning as described above, and Q1, Q2 and Q3 have the following meanings.
- examples of the compounds included in the present invention include the compounds synthesized in the above Examples. Tables 4 to 6 show, but the present invention is limited by these. It is not something to be done. (Table 4)
- F F F F F P F F CCCCCCHCCCCC e F HHHHHHHHHH H F F NNNNNNNNNNN F F C
- Some of the compounds of the present invention may be used as herbicides for upland fields and non-cultivated lands, such as Solanum nigrum, Datura stramonium, etc. in any of the soil treatment and foliage treatment methods.
- Solanaceae Solanaceae
- Stinging Abutilon theophrasti
- American stag stag Sida spinosa
- Malvaceae weeds Malva morning glory (Ipomoea purpurea), etc.
- Convolvulaceae weeds Amaranthaceae weeds represented by Ainant (Araaranthus lividus), Ae abyss (Amaranthus retrof lexus), etc., and Xant i um pensyl vanicum ragweed (Ambrosia, ⁇ ambrosia) Chrysanthemums (Compositae) Typhoids (Compositae), typified by Li (Helianthus annuus), Thorny Thorn (Galinsoga ciliata)> Thorny Thorn Asami (Cirsium arvense), Nohogiku (Senecio vulgaris), and Himenyong (Er igeron annus) (Roripp a indica), Brassicaceae (Cruciferae) weeds such as sapapis arvensis (sinapis arvensis) and sap (Apsella Bursapast oris), Polygonum B1 umei
- grasses Commelinaceae (Commelinaceae) L., Liliaura purpureum (Lamiura purpureum), etc., and Euonybia (Euphorbia supina), Euphorbiaceae (Euphorbiaceae) weeds, such as Euonybia maculata, etc., Rubiaceae weeds, such as Yaemdara (Galium spur i urn), Akane (Rubia akane), and violets (Viola mandsica) (Violaceae) weeds, such as vegetation, and legumes (such as Aesi kanakkusanem (Sesbania exaltata) and Cassia obtusifolia) Leguminosae) Broad-leaved weeds such as weeds, wild sorghum (Sorgham bicolor), oak sakihi (Pan i cum dichotomif lorum), syonhum grass (Sorghum halepense
- both soil treatment and foliage treatment under flooded conditions such as Heroda mosquito (Alisma canal iculatum), Omodaka (Sagittaria tri folia), Perica (Sagittaria pygmaea), etc.
- Scrothulariaceae weeds such as Lazenia (Lindernia pyxida ria), Potender iaceae weeds such as Monoc horia vaginalis, and mosquitoes such as Potamogeton distinctus. .) Remushi Oral (Potamogetona ceae) Weeds, Lythrace ae weeds represented by Rotala indica, etc., Echinochloa oryzicola, Echinochlo a crus-gal 1 i var. iormosensi s Echinochloa crus-gal 11 var. Cr us-gal li) Has low herbicide and high herbicidal activity against various weeds and other paddy weeds.
- Lazenia Lindernia pyxida ria
- Potender iaceae weeds such as Monoc horia vaginalis
- mosquitoes such as Potamo
- some of the compounds of the present invention have high safety against important crops such as rice, wheat, barley, sorghum, peanuts, corn, soybean, cotton, beet and the like.
- 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.
- Preferred herbicides to be used in admixture with the compound of the present invention include, for example, pyrazosulfuronethyl (common name), bensuliuron-methyl / 7 (common name), and sinosulfuron (cinosuluron).
- furonZ generic name, imazosuliuron (name), azimsulfuron (azimsul furonZ generic name), halosulfuron-methyl (halosuliuron-methyl no generic name), pretilachlor Z (pretilachlorZ—generic name), esprocarb / —esprocarb / — Generic name), pyrazolate (pyrazote / —generic name), birazoxyphen (pyrazoxyien ⁇ —generic name), benzophenap (benzofenapZ—generic name), Daimron (daimuronZ—generic name), promobutide (bromobutide / —generic name), nabroanili De (naproani 1 i de Z—generic name), clomeprop (cloraeprop no generic name), CNP (—generic ), Chromethoxynil (common name), Bifox (biienox
- the compound of the present invention When using the compound of the present invention, it is usually mixed with an appropriate solid carrier or liquid carrier, and if necessary, a surfactant, a penetrant, a spreading agent, a thickener, a deicing agent, a binder, a solid Adds anti-caking agent, disintegrant, antifoaming agent, preservative, anti-decomposition agent, etc., solution, emulsion, wettable powder, water solvent, water dispersible granule, water dispersible granule, water dispersible granule, suspension, emulsion It can be put to practical use in preparations of any dosage form, such as saspoe marjillon, microemulsion, powders, granules and gels.
- any dosage form can be provided by being enclosed in a water-soluble package. If necessary, it can be used in combination with a plurality of other herbicides, insecticides, fungicides, plant growth regulators, fertilizers, and the like at the time of formulation or spraying.
- solid carriers examples include quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, and other minerals such as calcium carbonate, ammonium sulfate. And inorganic salts such as sodium sulfate, sodium chloride, synthetic silica, and synthetic silicate.
- liquid carrier examples include alcohols such as ethylene glycol, propylene glycol and isopropanol, xylene, alkyl benzene and alkyl naphthalene.
- Aromatic hydrocarbons such as phthalene, ethers such as butyl sorbet, ketones such as cyclohexanone, esters such as y-butyrolactone, N-methylpyrrolidone, N-octylpyrrolidone
- water for vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil.
- solid and liquid carriers may be used alone or in combination of two or more.
- the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styrylphenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, and sorbitan.
- Nonionic surfactants such as fatty acid esters and polyoxyethylene sorbitan fatty acid esters, alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates Salts of formalin condensates of naphthalenesulfonic acid, salts of formalin condensates of alkylnaphthalenesulfonic acids, polyoxyethylene alkylaryl ether sulfates and phosphates Anionic surfactants such as polyoxyethylene styryl phenyl ether sulfates and phosphates, polycarboxylic acid salts and polystyrene sulfonates, and cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts Further examples include ampho
- the content of these surfactants is not particularly limited, but is usually preferably 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.
- Other examples include an antifreezing agent and a thickener.
- Other examples include a binder and a decomposition inhibitor.
- anti-drift agent examples include an anti-drift agent and an anti-decomposition agent.
- the above is uniformly mixed and ground to form a wettable powder.
- Non-ionic surfactant Kao Corporation
- the above is uniformly mixed and ground to form a powder.
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- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
L'invention se rapporte à des composés représentés par la formule générale (I) ou à des sels de ces composés; et à des pesticides et herbicides contenant lesdits composés en tant que principe actif. Dans la formule (I), Ra est hydrogène, cyano ou analogue; X est hydrogène, alkyle C1-4 ou analogue; Y est O ou S; Z1 et Z2 sont chacun indépendamment N ou CRb, où Rb est hydrogène, halogéno ou analogue, à condition que lorsque Z1 est N, Z2 est Cra, tandis que lorsque Z1 est Cra, Z2 est N; et Q est un groupe représenté par la formule générale (i), (ii), (iii), (iv) ou analogue. Dans ces formules, R1 et R2 sont chacun indépendamment hydrogène ou halogéno; R3 est hydrogène, halogéno ou analogue; R4 est hydrogène, halogéno ou analogue; R5 est hydrogène, halogéno ou analogue; R6 et R7 sont chacun indépendamment hydrogène, halogéno ou analogue; et R8 et R9 sont chacun indépendamment hydrogène, alkyle C¿1-8? ou analogue.
Priority Applications (1)
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AU2001241195A AU2001241195A1 (en) | 2000-03-17 | 2001-03-19 | Pyrimidinone derivatives and herbicides |
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JP2000076493 | 2000-03-17 | ||
JP2000-76493 | 2000-03-17 | ||
JP2000-357541 | 2000-11-24 | ||
JP2000357541 | 2000-11-24 |
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WO2001068613A1 true WO2001068613A1 (fr) | 2001-09-20 |
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PCT/JP2001/002158 WO2001068613A1 (fr) | 2000-03-17 | 2001-03-19 | Dérivés pyrimidinone et herbicides |
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AU (1) | AU2001241195A1 (fr) |
WO (1) | WO2001068613A1 (fr) |
Cited By (6)
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WO2016031987A1 (fr) * | 2014-08-29 | 2016-03-03 | 国立大学法人東京大学 | Dérivé de pyrimidone ayant une activité inhibitrice de l'autotaxine |
WO2016052247A1 (fr) * | 2014-10-03 | 2016-04-07 | 住友化学株式会社 | Composé pyrimidinone |
WO2017090654A1 (fr) * | 2015-11-26 | 2017-06-01 | 住友化学株式会社 | Composition antiparasitaire et son utilisation |
CN106831618A (zh) * | 2015-12-04 | 2017-06-13 | 沈阳中化农药化工研发有限公司 | 一种季铵盐类化合物及其应用 |
US10183949B2 (en) | 2014-08-29 | 2019-01-22 | The University Of Tokyo | Pyrimidinone derivative having autotaxin-inhibitory activity |
WO2019065570A1 (fr) * | 2017-09-26 | 2019-04-04 | 住友化学株式会社 | Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles le contenant |
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WO2017090654A1 (fr) * | 2015-11-26 | 2017-06-01 | 住友化学株式会社 | Composition antiparasitaire et son utilisation |
CN106831618A (zh) * | 2015-12-04 | 2017-06-13 | 沈阳中化农药化工研发有限公司 | 一种季铵盐类化合物及其应用 |
WO2019065570A1 (fr) * | 2017-09-26 | 2019-04-04 | 住友化学株式会社 | Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles le contenant |
CN111164081A (zh) * | 2017-09-26 | 2020-05-15 | 住友化学株式会社 | 杂环化合物和含有该杂环化合物的有害节肢动物防除剂 |
JPWO2019065570A1 (ja) * | 2017-09-26 | 2020-11-26 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除剤 |
US11084815B2 (en) | 2017-09-26 | 2021-08-10 | Sumitomo Chemical Company, Limited | Heterocyclic compound and harmful arthropod controlling agent containing same |
CN111164081B (zh) * | 2017-09-26 | 2022-08-12 | 住友化学株式会社 | 杂环化合物和含有该杂环化合物的有害节肢动物防除剂 |
JP7219717B2 (ja) | 2017-09-26 | 2023-02-08 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除剤 |
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