JP7472113B2 - ピリダジノン除草剤及び除草剤を製造するために使用されるピリダジノン中間体 - Google Patents
ピリダジノン除草剤及び除草剤を製造するために使用されるピリダジノン中間体 Download PDFInfo
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- JP7472113B2 JP7472113B2 JP2021517242A JP2021517242A JP7472113B2 JP 7472113 B2 JP7472113 B2 JP 7472113B2 JP 2021517242 A JP2021517242 A JP 2021517242A JP 2021517242 A JP2021517242 A JP 2021517242A JP 7472113 B2 JP7472113 B2 JP 7472113B2
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- pyridazinone
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- 239000000543 intermediate Substances 0.000 title description 15
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- 230000000885 phytotoxic effect Effects 0.000 description 1
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- RLQCYSVYYHHLIL-UHFFFAOYSA-M potassium;3,6-dichloropyridine-2-carboxylate Chemical compound [K+].[O-]C(=O)C1=NC(Cl)=CC=C1Cl RLQCYSVYYHHLIL-UHFFFAOYSA-M 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 1
- DWSPRBSLSXQIEJ-UHFFFAOYSA-N pyrasulfotole Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1S(C)(=O)=O DWSPRBSLSXQIEJ-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical class C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000003620 semiochemical Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 210000002377 thylakoid Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- ZWDZFMQAIVHFHF-UHFFFAOYSA-N zinc;2,2,6,6-tetramethylpiperidin-1-ide Chemical group [Zn+2].CC1(C)CCCC(C)(C)[N-]1.CC1(C)CCCC(C)(C)[N-]1 ZWDZFMQAIVHFHF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
- C07D237/16—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen 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
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本開示は、ピリダジノン類及びピリダジノン類を製造するための方法を提供する。本明細書に開示されるピリダジノン類は、ピリダジノンベースの除草剤を製造するための合成中間体として使用され得るか又はピリダジノン除草剤として使用され得る。特許文献1及び特許文献2は、除草性ピリダジノン及び除草性ピリダジノンを製造するために使用される合成中間体を開示する。改善された除草性ピリダジノン及び除草性ピリダジノンを製造するための改善された方法の必要性が存在する。
一態様において、本開示は、式I
R1はC1-C4アルキル又はC3-C6シクロアルキルであり;
R2はH、Cl、Br又はIであり;
R3はCl又はOR4であり;
R4はH又はC1-C4アルキルであり;
R5はH、F、Cl又はCH3であり;そして
R6はH又はClである]
の化合物及びそのN-オキシド又は塩を提供する。
R1はC1-C4アルキル又はC3-C6シクロアルキルであり;
R2はH又はClであり;
R5はH、F、Cl又はCH3であり;そして
R6はH又はClである]
の化合物を製造するための方法を提供し、該方法は:
R1はC1-C4アルキル又はC3-C6シクロアルキルであり;
GはC1-C4アルキル、SO2CF3又はSO2(4-Me-Ph)である]
の化合物と反応させることを含む。
R1はC1-C4アルキル又はC3-C6シクロアルキルであり;
R5はH、F、Cl又はCH3であり;そして
R6はH又はClである]
の化合物を製造するための方法を提供し、該方法は、上に示される式中R2がHである式I-Aの化合物を、メトキシル化剤と反応させることを含む。
R1はC1-C4アルキル又はC3-C6シクロアルキルであり;
R2はCl、Br又はIであり;
R5はH、F、Cl又はCH3であり;そして
R6はH又はClである]
の化合物を製造するための方法を提供し、該方法は:
(2) (1)において形成された式Vの亜鉛化中間体化合物をハロゲン化剤と反応させること
を含む。
R1はC1-C4アルキル又はC3-C6シクロアルキルであり;
R2はCl、Br又はIであり;
R5はH、F、Cl又はCH3であり;そして
R6はH又はClである]
の化合物を製造するための方法を提供し、該方法は、上に示される式I-Cの化合物を脱メチル化剤と反応させることを含む。
R1はC1-C4アルキル又はC3-C6シクロアルキルであり;
R5はH、F、Cl又はCH3であり;そして
R6はH又はClである]
の化合物を製造するためのさらなる方法を提供し;
R1はC1-C4アルキル又はC3-C6シクロアルキルであり、
R5はH、F、Cl又はCH3であり;そして
R6はH又はClである]
の化合物をオキシ塩化リンと反応させることを含む。
R1はC1-C4アルキル又はC3-C6シクロアルキルであり;
R5はH、F、Cl又はCH3であり;そして
R6はH又はClである]
の化合物を製造するためのさらなる方法を提供し;
本明細書で使用されるように、用語「含む(comprises)」、「含むこと(comprising)」、「含む(includes)」、「含むこと(including)」、「有する」、「有すること」、「含有する」、「含有すること」、「を特徴とする」又はそれらの任意の変形は、明示的に示される任意の限定の支配下での包括的な包含を対象とすることを意図される。例えば、要素のリストを含むプロセス又は方法は、必ずしもそれらの要素だけに限定されないが、明確にリストに記載されていないか又はそのような構成のプロセス若しくは方法に固有の他の要素を含んでいてもよい。
実施形態A1.発明の要旨に記載される式Iの化合物及びそのN-オキシド又は塩。
5-クロロ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン;
5-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-2-メチル-3(2H)-ピリダジノン;
5-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン;
4-(2,7-ジメチル-1-ナフタレニル)-5-メトキシ-2-メチル-3(2H)-ピリダジノン;
6-クロロ-5-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン;及び
6-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-5-メトキシ-2-メチル-3(2H)-ピリダジノン
から選択される実施形態A1の化合物(すなわち、式Iの化合物)。
(a) R3がOR4であり;R4がHであり;かつR5がHである場合、R6はClであり;そして
(b) R2がBrであり:R3がOR4であり;かつR4がHである場合、R6はHである。
実施形態B1.発明の要旨に記載される、式I-Aの化合物を製造するための方法。
実施形態C1.発明の要旨に記載される、式I-Bの化合物を製造するための方法。
実施形態D1.発明の要旨に記載される、式I-Cの化合物を製造するための方法。
実施形態E1.発明の要旨に記載される、式I-Dの化合物を製造するための方法。
実施形態F1.発明の要旨に記載される、式I-Eの化合物を製造する方法。
実施形態G1.発明の要旨に記載される、式I-Eの化合物を製造するための方法。
R12はH、C1-C6アルキル、C1-C6ハロアルキル又はC4-C8シクロアルキルであり;
R13はH、C1-C6アルキル又はC1-C6アルコキシであり;
Q1は、フェニル、チエニル、ピリジニル、ベンゾジオキソリル、ナフチル、ナフタレニル、ベンゾフラニル、フラニル、ベンゾチオフェニル及びピラゾリルからなる群から選択される、場合により置換された環系であり、ここで置換されている場合、上記環系は1~3個のR14で置換され;
Q2は、フェニル、ピリジニル、ベンゾジオキソリル、ピリジノニル、チアジアゾリル、チアゾリル、及びオキサゾリルからなる群から選択される、場合により置換された環系であり、ここで置換されている場合、上記環系は1~3個のR15で置換され;
各R14は独立して、ハロゲン、C1-C6アルキル、C1-C6ハロアルキル、C1-C6アルコキシ、C1-C6ハロアルコキシ、C3-C8シクロアルキル、シアノ、C1-C6アルキルチオ、C1-C6アルキルスルフィニル、C1-C6アルキルスルホニル、SF5、NHR17;又は1~3個のR16で場合により置換されたフェニルであり;又は1~3個のR16で場合により置換されたピラゾリルであり;
各R15は独立して、ハロゲン、C1-C6アルキル、C1-C6ハロアルキル、C1-C6アルコキシ、C1-C6ハロアルコキシ、シアノ、ニトロ、C1-C6アルキルチオ、C1-C6アルキルスルフィニル、C1-C6アルキルスルホニルであり;
各R16は独立して、ハロゲン、C1-C6アルキル又はC1-C6ハロアルキルであり;
R17はC1-C4アルコキシカルボニルである]
の化合物も含まれる。
R18はH、C1-C6アルキル、C1-C6ハロアルキル又はC4-C8シクロアルキルであり;
各R19は独立して、ハロゲン、C1-C6ハロアルキル又はC1-C6ハロアルコキシであり;
pは0、1、2又は3の整数であり;
各R20は独立して、ハロゲン、C1-C6ハロアルキル又はC1-C6ハロアルコキシであり;そして
qは0、1、2又は3の整数である]
の化合物も含まれる。
6-クロロ-5-ヒドロキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノンの製造
工程A: 5-クロロ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン(化合物番号1)の製造
窒素雰囲気下で、マグネシウム(5.4g、0.22mol)をきれいな乾燥したフラスコ中に導入した。2~3個のヨウ素の結晶をマグネシウムを活性化させるために加えた。1-ブロモ-2-メチルナフタレン(31.0mL、0.20mol)のテトラヒドロフラン(200mL)溶液をマグネシウムに滴下した。溶液25mLを加えた後、滴下を止めて穏やかに徐々に発熱させた。少量の気泡が観察されたら、制御された活発な反応を維持する速度で滴下を継続した。滴下の終わりごろに、穏やかな還流を維持するように反応混合物を外部加熱した。反応混合物を滴下が完了した後1時間加熱した。グリニャール形成を、1N塩酸水溶液を用いてクエンチしたアリコートのHPLCによりモニタリングした。反応混合物を-55℃に冷却した。-40℃未満の反応温度を維持しながら、5-クロロ-4-メトキシ-2-メチル-3(2H)-ピリダジノン(34.9g、0.20mol)のテトラヒドロフラン(400mL)溶液をゆっくりと加えた。加え終わった後、冷却浴を外して反応混合物を室温まで昇温させた。反応混合物をさらに1時間撹拌し、そして完了をモニタリングした。完了したら、反応混合物を0℃に冷却し、1N塩酸水溶液(500mL)でクエンチし、そして18時間周囲温度で撹拌した。反応混合物をジクロロメタンで2回抽出した。抽出物を合わせてMgSO4で乾燥し、濾過し、そして濃縮した。濃縮物を18時間ヘキサンを用いてトリチュレーションした。得られた混合物を氷水浴で冷却し、濾過し、冷ヘキサンで洗浄して真空乾燥し、ベージュ色に着色した固形物(50.8g、収率88%)を得た。
1H NMR δ 7.90(s、1H)、7.85(m、2H)、7.40(m、3H)、7.30(m、1H)、3.87(s、3H)、2.29(s、3H)。
メタノール(180mL)中の5-クロロ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン(すなわち、工程Aで得られた生成物、50.8g、0.18mol)に、ナトリウムメトキシド(メタノール中25質量%、61mL、0.27mol)を加えた。反応混合物を溶媒の還流温度まで加熱した。18時間後に1H NMRにより反応をモニタリングし、出発物質が消費されたことを示した。反応混合物を0℃に冷却し、次いで水(500mL)を加えた。得られた混合物を濾過し、そして真空乾燥してベージュ色着色固形物を得た(40.9g、収率81%)。
1H NMR δ 7.90(s、1H)、7.80(m、2H)、7.40(m、4H)、3.85(s、3H)、3.66(s、3H)、2.28(s、3H)。
工程C-1: 乾燥フラスコ中の塩化亜鉛の溶液(2-メチルテトラヒドロフラン中2.9M、28mL、0.10mol)を、窒素雰囲気下で5℃に冷却した。2,2,6,6-テトラメチルピペリジニルマグネシウムクロリド 塩化リチウム錯体(テトラヒドロフラン/トルエン中1.0M、100mL、0.10mol)を、発熱温度を15℃に限定する速度でゆっくりと加えた。次いでこの混合物を室温まで昇温させて、次の工程で使用するためのビス(2,2,6,6-テトラメチルピペリジン)亜鉛、塩化マグネシウム、塩化リチウム錯体の透明0.39M溶液を得た。
1H NMR δ 7.85 (d、2H)、7.45(m、4H)、3.79(s、3H)、3.25(s、3H)、2.33(s、3H)。
6-クロロ-5-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン(14.1g、44.8mmol)のモルホリン(45mL)中混合物を1時間加熱還流し、続いて室温まで冷却した。この混合物をヘキサン(45mL)で希釈し、18時間撹拌し、そして濾過した。濾過した固形物を窒素流下で濾過用漏斗上で乾燥させた。固形物を1N塩酸水溶液(200mL)を用いてフラスコに移した。この混合物を3時間撹拌した。固形物を濾過し、そして真空乾燥して淡ベージュ色固体を得た(10.4g、収率77%)。
1H NMR (DMSO-d6) δ 10.89-11.27 (b、1H)、7.95(m、2H)、7.40(m、4H)、3.64(s、3H)、2.20(s、3H)。
6-クロロ-5-ヒドロキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノンの代替の製造
工程A: 5-クロロ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン(化合物番号1)の製造
1-ブロモ-2-メチルナフタレン(100g、452mmol)のテトラヒドロフラン(400mL)溶液に、マグネシウム削り状(21.7g、904mmol)及びヨウ素(20mg)を加えた。反応混合物を70℃に2時間加熱し、その時間の間に色は深緑色に変わり、そして激しい還流が見られた。テトラヒドロフラン(400mL)中の5-クロロ-4-メトキシ-2-メチル-3(2H)-ピリダジノン(65g、373mmol)を別の丸底フラスコに取り、上記の反応混合物を-100℃で加え、そして反応混合物を周囲温度で4時間撹拌した。石油エーテル中20%酢酸エチルでのTLC分析は反応の完了を示した。次いで反応混合物を飽和NH4Cl溶液でクエンチし、そして酢酸エチルで2回抽出した。合わせた有機層を水、ブラインで洗浄し、そしてNa2SO4で乾燥した。溶媒をエバポレートして粗生成物を得た。粗製化合物を石油エーテルで洗浄して標題化合物84g(収率65.3%)を灰色がかった白色の固体として得た。
5-クロロ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン(すなわち、工程Aで得られた化合物、500g、1.76mol)のジオキサン(5.0L)溶液に、メタノール中30%ナトリウムメトキシド(949mL、5.26mol)を室温で加え、そして反応混合物を110℃で2時間撹拌した。50%酢酸エチル/石油エーテルでのTLCによる分析は反応の完了を示した。反応混合物を氷水に注ぎ、飽和NH4Cl溶液でクエンチし、そしてジクロロメタンで2回抽出した。合わせた有機層を水、ブライン及びで洗浄し、そしてNa2SO4で乾燥した。溶媒をエバポレートして粗生成物を得、これを石油エーテルで洗浄して表題化合物449g(収率91.2%)を固体として得た。
丸底フラスコにZnCl2(194g、1.42mol)を取り、そしてテトラヒドロフラン中1M 2,2,6,6-テトラメチルピペリジニルマグネシウムクロリド塩化リチウム錯体(2378mL、2.37mol)を加え、そして反応混合物を周囲温度で2時間撹拌した。5-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン(すなわち、工程Bで得られた生成物、333g、1.18mol)及び1,3-ジクロロ-5,5-ジメチルヒダントイン(281g、1.42mol)を少しずつ加え、そして反応混合物を室温で16時間撹拌した。30%酢酸エチル/石油エーテルでのTLC分析は反応の完了を示した。反応混合物を氷水に注ぎ、飽和炭酸水素ナトリウム溶液でクエンチし、そしてジクロロメタンで2回抽出した。合わせた有機層を水、ブラインで洗浄し、そしてNa2SO4で乾燥した。溶媒をエバポレートして粗生成物を得た。粗生成物をジエチルエーテル/石油エーテルで洗浄して表題化合物205g(収率55%)を白色固体として得た。
モルホリン(1.2L)中の6-クロロ-5-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン(すなわち、工程Cで得られた生成物、410g、1.30mol)を120℃で2時間撹拌した。50% 酢酸エチル/石油エーテルでのTLC分析は反応の完了を示した。次いで反応混合物をエバポレートし、濃塩酸で酸性化し、そして1時間周囲温度で撹拌した。反応混合物を濾過し、過剰の水で洗浄し、そして真空下で乾燥して表題化合物290g(収率74.3%)を灰色がかった白色の固体として得た。
6-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-5-ヒドロキシ-2-メチル-3(2H)-ピリダジノン(化合物番号20)の製造:
工程A.5-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-2-メチル-3(2H)-ピリダジノン(化合物番号4)の製造:
マグネシウム削り状(4.22g、173mmol、乳棒と乳鉢で秤量前に部分的に粉砕した)を、滴下漏斗、大きい磁気撹拌子、及び還流冷却器を備えた1L 三口丸底フラスコに入れた。マグネシウムをN2流下でゆっくりと撹拌しながらこの装置をヒートガンで加熱した。冷却した後、少量のヨウ素結晶(80mg)を加え、混合物を再び短時間加熱し(赤褐色蒸気が観察された)、次いで 1-ブロモ-2,7-ジメチルナフタレン(35.2g、0.15モル)及びテトラヒドロフラン(80mL)の溶液を5mLだけ加えた。発泡しながら反応混合物の色は急速に赤褐色から淡青色に変化し始めた。1-ブロモ-2,7-ジメチルナフタレン及びテトラヒドロフランの溶液を、穏やかな還流を維持するような速度でゆっくりと加えた(合計時間約30分)。得られた混合物を64mLテトラヒドロフランで希釈し、1時間還流させ、次いで-40℃に冷却した。次いで、5-クロロ-4-メトキシ-2-メチル-3(2H)-ピリダジノン(21.7g、124mmol)及びテトラヒドロフラン(80mL)の溶液を加え、そして得られた溶液を周囲温度で14時間撹拌した。得られた混合物を氷/水で冷却し、そして飽和NH4Cl水溶液(100mL)を<15℃で加えてクエンチした。得られた混合物を酢酸エチル(1.2L)と飽和NH4Cl水溶液(1L)との間で分配し、水層を酢酸エチル(500mL)で抽出し、そして合わせた有機層を飽和NH4Cl、ブラインで洗浄し、MgSO4で乾燥し、そして濃縮して粗製5-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-2-メチル-3(2H)-ピリダジノン38.1g(85%)を得、これをさらに精製することなく次の工程で使用した。粗生成物は、2,7-ジメチルナフタレンを含む少量の副生成物を含有していた。分析サンプルを、ヘキサン中0~50%酢酸エチルで溶出するシリカゲルカラム上でのMPLCにより準備した。
1H NMR(500MHz) δ 7.95(s、1H)、7.79(d、1H)、7.74(d、1H)、7.35(d、1H)、約7.26(dd、1H)、7.03(br s、1H)、3.88(s、3H)、2.42(s、3H)、2.26(s、3H)。
工程Aからの粗製5-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-2-メチル-3(2H)-ピリダジノン(すなわち、工程Aで得られた生成物、38.1g、12 8mmol)及びジオキサン(890mL)の溶液を、NaOMe(MeOH中25%溶液、87mL、383mmol)で処理した。得られた暗褐色混合物を16時間加熱還流し、冷却し、そして濃縮してジオキサンの大部分を除去した。得られた残留物をCH2Cl2と過剰の飽和NH4Cl水溶液との間で分配し、水層(pH約10)をCH2Cl2で抽出し、そして合わせた有機物を飽和NH4Cl、ブラインで洗浄し、MgSO4で乾燥し、そして濃縮して褐色油状スラリー57gを得た。このスラリーをジエチルエーテルを用いてトリチュレーションしてベージュ色固形物が生じ、これを濾過により単離し、いくらかのジエチルエーテルで洗浄し、そしてフリット(frit)上で乾燥して4-(2,7-ジメチル-1-ナフタレニル)-2-メチル-3(2H)-ピリダジノンをベージュ色固体として得た(10.6g、28%)。1H NMR分析は高い純度の所望の生成物を示した。上記からの濾液を濃縮して、暗褐色油状残留物を得、これをエーテル及びヘキサンを用いてトリチュレーションして追加の化合物(2.2g、6%)を得た。
1H NMR (500MHz) δ 7.92(s、1H)、7.73(d、1H)、7.71(d、1H)、7.32(d、1H)、7.22(dd、1H)、7.11(br s、1H)、3.87(s、3H)、3.70(s、3H)、2.41(s、3H)、2.26(s、3H)。
4-(2,7-ジメチル-1-ナフタレニル)-5-メトキシ-2-メチル-3(2H)-ピリダジノン(すなわち、工程Bで得られた生成物、27.2g、92mmol)及びCH2Cl2(646mL)の溶液を氷/アセトン浴で-10℃に冷却した。ビス(2,2,6,6-テトラ-メチルピペリジン)亜鉛、塩化マグネシウム、塩化リチウム錯体のテトラヒドロフラン/2-メチルテトラヒドロフラン中溶液(約0.40M溶液231mL、約92mmol)を<0℃で加えた。得られた混合物を水浴を用いて18℃に加温し、15分撹拌し、次いで-15℃に冷却した。1,3-ジクロロ-5,5-ジメチルヒダントイン(21.8g、111mmol)を少しずつ加えて温度を<-10℃に維持した。得られた混合物を周囲温度まで加温し、そして7時間撹拌した。得られた混合物を-10℃に冷却し、そしてメタ重亜硫酸ナトリウムの溶液(50g)でクエンチし、そして水(250mL)を<0℃で加えた。得られた混合物を高速で撹拌しながら、1時間かけて周囲温度まで昇温させた。得られた混合物をCH2Cl2(600mL)及び水(300mL)で希釈し、水層をCH2Cl2(300mL)で抽出し、そして合わせた有機物を飽和塩化アンモニウム水溶液(2x500mL)、ブライン(300mL)で洗浄し、MgSO4で乾燥し、そして濃縮して褐色油状物50gを得た。粗生成物を分取MPLCにより750gカラムで、ヘキサン中20~100%酢酸エチルで溶出して精製した。所望の生成物6-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-2-メチル-3(2H)-ピリダジノンが最初に溶出された(11.2g、37%及び最初のフラクション中のわずかに純粋でない所望の生成物3.3g)。さらなる溶出により、未反応の4-(2,7-ジメチル-1-ナフタレニル)-2-メチル-3(2H)-ピリダジノンが回収された(10.2g、回収38%)。
1H NMR (500 MHz) δ 7.78 (d、1H)、7.73 (d、1H)、7.32 (d、1H)、ca.7.25 (dd、1H)、7.15 (br s、1H)、3.80(s、3H)、3.26(s、3H)、2.45(s、3H)、2.30(s、3H)。
6-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-5-メトキシ-2-メチル-3(2H)-ピリダジノン(すなわち、工程Cにおいて得られた生成物、6.9g、21mmol)及びモルホリン(21mL)の懸濁液を穏やかに還流させて1時間加熱し、室温まで冷却し、そして濃塩酸(30mL)と氷(約200mL)との混合物中に注いだ。この混合物をCH2Cl2(2x200mL)で抽出し、そして合わせた有機層を飽和NH4Cl(2x100mL)で洗浄し、MgSO4で乾燥し、そして濃縮して表題化合物6.0g(収率91%)を明黄色固体として得た。mp=232~234℃。
1H NMR(500MHz) δ 7.83(d、1H)、7.75(d、1H)、7.38(d、1H)、7.29(dd、1H)、7.13(br s、1H)、5.55(v br s、1H)、3.83(s、3H)、2.44(s、3H)、2.28(s、3H)。
6-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-5-ヒドロキシ-2-メチル-3(2H)-ピリダジノン(化合物番号20)の代替の製造:
工程A: 2,7-ジメチルナフタレンの製造
2,7-ジブロモナフタレン(250g、0.877mol)のジオキサン(4L)溶液に、Pd(dppf)Cl2及びトルエン中2Mジメチル亜鉛(2.19L、4.38mol)を室温で加えた。反応混合物を100℃で16時間撹拌した。ヘキサンでのTLC分析は反応の完了を示した。反応混合物を酢酸エチルで希釈し、そして氷水に注いだ。合わせた有機層を水、ブラインで洗浄し、そして硫酸ナトリウムで乾燥した。溶媒をエバポレートして粗生成物を得、これをシリカゲルカラム上にチャージした。このカラムを石油エーテルで溶出して表題生成物111g(収率81%)を白色固体として得た。
2,7-ジメチルナフタレン(すなわち、工程Aで得られた生成物、282g、1.8mol)のCH3CN(2.8L)及びN,N-ジメチルホルムアミド(200mL)中の溶液にN-ブロモコハク酸イミド(321g、1.8mol)を加え、そして反応混合物を室温で16時間撹拌した。ヘキサンでのTLC分析は反応の完了を示した。反応混合物を氷水に注ぎ、そして石油エーテルで三回抽出した。合わせた有機層を水、ブラインで洗浄し、そしてNa2SO4で乾燥した。溶媒をエバポレートして粗生成物を得、これをシリカゲルクロマトグラフィーにより石油エーテルで溶出して精製し、表題生成物415g(収率97%)を淡黄色固体として得た。
1-ブロモ-2,7-ジメチルナフタレン(すなわち、工程Bで得られた生成物、100g、0.42mol)のテトラヒドロフラン(500mL)中溶液に、マグネシウム削状(20.42g、0.851mol)及びヨウ素(20mg)を加えた。反応混合物を70℃で2時間過加熱し、その時間の間に反応混合物の色は深緑色に変わった(激しい還流が観察された)。上で準備したグリニャール試薬を、5-クロロ-4-メトキシ-2-メチル-3(2H)-ピリダジノン(61.1g、0.351mol)のテトラヒドロフラン(500mL)中の溶液に加え、そして反応混合物を室温で4時間撹拌した。20%酢酸エチル/石油エーテルでのTLCによる分析は反応の完了を示した。反応混合物を飽和NH4Cl溶液でクエンチし、そして酢酸エチルで2回抽出した。合わせた有機層を水、ブラインで洗浄し、そしてNa2SO4で乾燥した。溶媒をエバポレートして粗生成物を得た。粗生成物を石油エーテルで洗浄して表題化合物82g(収率64%)を白色固体として得た。
5-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-2-メチル-3(2H)-ピリダジノン(すなわち、工程Cにおいて得られた生成物、365g、1.2mol)のジオキサン(3.6L)中溶液に、メタノール中30%NaOMe(661mL、3.6mol)を室温で加え、そして反応混合物を110℃で2時間撹拌した。50%酢酸エチル/石油エーテルでのTLCによる分析は反応の完了を示した。反応混合物を氷水に注ぎ、飽和NH4Cl溶液dエクエンチし、そしてジクロロメタンで2回抽出した。合わせた有機層を水、ブラインで洗浄し、そしてNa2SO4で乾燥した。溶媒をエバポレートして粗生成物を得た。粗生成物を石油エーテルで洗浄して純粋な表題生成物355g(収率98%)を灰色がかった白色の固体として得た。
丸底フラスコに、ZnCl2(65g、0.47mol及びテトラヒドロフラン中1M 2,2,6,6-テトラメチルピペリジニルMgCl2LiCl(952mL、0.952mol)を加え、そして反応混合物を室温d2時間撹拌した。4-(2,7-ジメチル-1-ナフタレニル)-5-メトキシ-2-メチル-3(2H)-ピリダジノン(すなわち、工程Dで得られた生成物、140g、0.476mol)及び1,3-ジクロロ-5,5-ジメチルヒダントイン(112g、0.571mol)を少しずつ加え、そして反応混合物を室温で16時間撹拌した。30%酢酸エチル/石油エーテルでのTLC分析は反応の完了を示した。反応混合物を氷水に注ぎ、飽和亜硫酸水素ナトリウム溶液でクエンチ子、そしてジクロロメタンで2回抽出した。合わせた有機層を水、ブラインで洗浄し、そしてNa2SO4で乾燥した。溶媒をエバポレートして粗生成物を得た。粗製化合物をジエチルエーテル/石油エーテルで洗浄して82g(収率52%)を灰色がかった白色の固体として得た。
モルホリン(650mL)中の6-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-5-メトキシ-2-メチル-3(2H)-ピリダジノン(すなわち、工程Eで得られた生成物、208g、0.634mol)を120℃で2時間撹拌した。50%酢酸エチル/石油エーテルでのTLC分析は反応の完了を示した。反応混合物をエバポレートし、濃塩酸で酸性化し、そして1時間室温で撹拌し、その時間の間に固体が沈殿した。この固体を濾過し、過剰の水で洗浄し、そして真空下で乾燥して表題化合物195g(収率98%)を灰色がかった白色の固体として得た。
5-クロロ-6-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノンの製造
工程A: 6-アミノ-5-クロロ-4-メトキシ-2-メチル-3(2H)-ピリダジノンの製造
メタノール中のナトリウムメトキシドの溶液(4.8mL、4.4M溶液、21.0mmol)を、6-アミノ-4,5-ジクロロ-2-メチル-3(2H)-ピリダジノン(3.70g、19.1mmol)及びジオキサン(95mL、無水)の懸濁液に氷水浴で冷却しながら加えた。得られた懸濁液を周囲温度で3時間撹拌し、飽和塩化アンモニウム水溶液(150mL)に注ぎ、そして得られた混合物を塩化メチレン(150mL)抽出した。水層を塩化メチレンで2回以上抽出した。合わせた有機抽出物を無水MgSO4で乾燥し、濾過し、そして濃縮して表題化合物3.45gを黄色半固体として得た。
1H NMR (500MHz) δ 4.34(br s、2H)、4.29(s、3H)、3.60(s、3H)。
6-アミノ-5-クロロ-4-メトキシ-2-メチル-3(2H)-ピリダジノン(すなわち、工程Aで得られた生成物、529mg、2.8mmol)、塩化銅(II)(618mg、4.6mmol)及びアセトニトリル(8mL、無水)の溶液に、亜硝酸tert-ブチル(0.48mL、90質量%、3.6mmol)を氷水浴で冷却しながら加えた。得られた混合物を周囲温度で1時間撹拌し、次いで酢酸エチルと飽和塩化アンモニウム水溶液との間で分配した。有機層を飽和塩化アンモニウム水溶液で洗浄し、無水MgSO4で乾燥し、濾過し、そして濃縮して標題化合物0.51gを黄色半固体として得た。
1H NMR(500MHz) δ 4.33(s、3H)、3.74(s、3H)。
5,6-ジクロロ-4-メトキシ-2-メチル-3(2H)-ピリダジノン(すなわち、工程Bにおいて得られた生成物、0.41g、1.9mmol)を、2-メチル-1-ナフタレニル-マグネシウムブロミド(9.0mL、テトラヒドロフラン中0.25M溶液、2.3mmol)を-20℃で加えた。得られた混合物を周囲温度で30分間撹拌し、その時点で反応混合物を5℃に冷却し、そして飽和塩化アンモニウム水溶液(3mL)でクエンチした。得られた混合物を酢酸エチルと飽和塩化アンモニウム水溶液との間で分配し、得られた有機層を飽和塩化アンモニウム水溶液で洗浄し、無水MgSO4で乾燥し、濾過し、そして濃縮して表題化合物0.69gを粗製形態で得て、これをさらに精製することなくその後の工程で使用した。分析サンプルを、シリカカラム上でのMPLCによりヘキサン中0%~100%酢酸エチルで溶出して精製することにより製造した。
1H NMR(500MHz) δ 7.87-7.85(m、2H)、7.47-7.40(m、3H)、7.30-7.27(m、1H)、3.86(s、3H)、2.29(s、3H)。
固形カリウムメトキシド(0.29g、3.4mmol)を、5,6-ジクロロ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン(すなわち、工程Cで得られた生成物、粗生成物0.69g、約1.7mmol)及びトルエン(17mL)の溶液に周囲温度で加えた。得られた混合物を周囲温度で3日間撹拌し、氷水浴で冷却し、そして飽和塩化アンモニウム水溶液(10mL)でクエンチした。得られた混合物を酢酸エチルと飽和塩化アンモニウム水溶液との間で分配した。有機層を無水MgSO4で乾燥し、濾過し、そして濃縮して標題化合物0.60gを粗製形態で得て、これをさらに精製することなくその後の工程で使用した。粗生成物の1H NMR分析は、所望の生成物、6-クロロ-5-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン、異性体、5-クロロ-6-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン、及び未反応の5,6-ジクロロ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノンのそれぞれ3.0:1.0:2.8の比の混合物を示した。分析サンプルを、シリカでのMPLCによりヘキサン中0%~100%酢酸エチルのグラジエントにより得た。
6-クロロ-5-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン:
1H NMR(500MHz) δ 7.84(歪んだd、2H)、7.47-7.38(m、4H)、3.80(s、3H)、3.26(s、3H)、2.33(s、3H)。
5-クロロ-6-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン:
1H NMR(500MHz) δ 7.86-7.83(m、2H)、7.45-7.37(m、3H)、7.33-7.30(m、1H)、4.01(s、3H)、3.77(s、3H)、2.29(s、3H)。
工程A.6-クロロ-5-ヒドロキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノンの製造
モルホリン(2mL)並びに6-クロロ-5-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン、5-クロロ-6-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン及び5,6-ジクロロ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノンの混合物を含有する合成実施例5、工程Dからの粗生成物(0.60g)の溶液を、110℃に2時間加熱した。得られた混合物を濃縮し、そして残留物をジエチルエーテルでトリチュレーションした。得られた固体を濾過し、ジエチルエーテルで洗浄し、そしてフリット上で乾燥して6-クロロ-5-ヒドロキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノンのモルホリン塩を得た。濾液は未反応の5-クロロ-6-メトキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン及び5,6-ジクロロ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノンを含有していた。固形6-クロロ-5-ヒドロキシ-2-メチル-4-(2-メチル-1-ナフタレニル)-3(2H)-ピリダジノン モルホリン塩を最小量のテトラヒドロフラン中に部分的に溶解し、そして得られた混合物を1N塩酸水溶液(10mL)に撹拌しながら徐々に加えた。得られた固体を濾過により単離し、1N塩酸水溶液で洗浄し、そしてフリット上で乾燥して表題生成物200mgを灰色がかった白色固体として得た。
1H NMR(500MHz) δ 7.92-7.86(m、2H)、7.48-7.40(m、6H)、3.83(s、3H)、2.33(s、3H)。
高強度濃縮物(High Strength Concentrate)
化合物番号22 98.5%
シリカエアロゲル 0.5%
合成非晶質微細シリカ 1.0%
水和剤
化合物番号22 65.0%
ドデシルフェノール ポリエチレングリコールエーテル 2.0%
リグニンスルホン酸ナトリウム 4.0%
アルミノケイ酸ナトリウム 6.0%
モンモリロナイト(焼成) 23.0%
(i) 粒剤
化合物番号22 10.0%
アタパルジャイト顆粒(低揮発性物質、0.71/0.30mm;U.S.S.No.25-50篩) 90.0%
押出成形ペレット
化合物番号22 25.0%
無水硫酸ナトリウム 10.0%
粗製リグニンスルホン酸カルシウム 5.0%
アルキルナフタレンスルホン酸ナトリウム 1.0%
カルシウム/マグネシウムベントナイト 59.0%
乳濁液
化合物番号22 10.0%
ヘキサオレイン酸ポリオキシエチレンソルビトール 20.0%
C6-C10脂肪酸メチルエステル 70.0%
マイクロエマルション
化合物番号22 5.0%
ポリビニルピロリドン-酢酸ビニルコポリマー 30.0%
アルキルポリグリコシド 30.0%
モノオレイン酸グリセリル 15.0%
水 20.0%
SC剤
化合物番号22 35%
ブチル ポリオキシエチレン/ポリプロピレンブロックブロックコポリマー
4.0%
ステアリン酸/ポリエチレングリコールコポリマー 1.0%
スリレンアクリルポリマー 1.0%
キサンタンガム 0.1%
プロピレングリコール 5.0%
シリコーン系消泡剤 0.1%
1,2-ベンゾイソチアゾリン-3-オン 0.1%
水 53.7%
EW剤(Emulsion in Water)
化合物番号22 10.0%
ブチル ポリオキシエチレン/ポリプロピレンブロックコポリマー 4.0%
ステアリン酸/ポリエチレングリコールコポリマー 1.0%
スチレンアクリルポリマー 1.0%
キサンタンガム 0.1%
プロピレングリコール 5.0%
シリコーン系消泡剤 0.1%
1,2-ベンゾイソチアゾリン-3-オン 0.1%
芳香族石油系炭化水素 20.0
水 58.7%
OD剤(Oil Dispersion)
化合物番号22 25%
ヘキサオレイン酸 ポリオキシエチレンソルビトール 15%
有機的に改良されたベントナイト粘土 2.5%
脂肪酸メチルエステル 57.5%
イヌビエ(Echinochloa crus-galli)、ホウキギ(Kochia scoparia)、ブタクサ(common ragweed、Ambrosia elatior)、ネズミムギ(Lolium multiflorum)、アキノエノコログサ(Setaria faberii)、エノコログサ(Setaria viridis)及びアオゲイトウ(pigweed)(Amaranthus retroflexus)から選択される植物種の種子をローム土及び砂のブレンド中に植え、そして界面活性剤を含む非植物毒性溶媒混合物中で製剤化された試験化学物質を使用して有向土壌スプレーを用い発生前処理した。
イネ(Oryza sativa)、タマガヤツリ(small-flower umbrella sedge、Cyperus difformis)、アメリカコナギ(Heteranthera limosa)及びイヌビエ(Echinochloa crus-galli)から選択される水田試験における植物種を、試験のために2葉期まで成長させた。処理の時点で、試験用鉢を土壌表面の上3cmまで水に浸し、試験化合物を水田の水に直接施用することにより処理し、その後その水深を試験の間維持した。処理された植物及び対照を温室内で13~15日間維持し、その期間後、全ての種を対照と比較し、そして視覚的に評価した。表Bにまとめられた植物応答評定は0~100のスケールに基づき、ここで0は効果無しであり、そして100は完全な対照である。ダッシュ記号(-)応答は試験の結果が無いことを意味する。
250g ai/ha 20 21 22 65
冠水
イヌビエ 25 80 40 40
アメリカコナギ 100 90 90 80
イネ 15 35 60 20
タマガヤツリ 90 90 85 90
ノスズメノテッポウ(Alopecurus myosuroides)、ネズミムギ(Lolium multiflorum)、秋播コムギ(Triticum aestivum)、ヤエムグラ(Galium aparine)、トウモロコシ(Zea mays)、オニメヒシバ(Digitaria sanguinalis)、アキノエノコログサ(Setaria faberii)、セイバンモロコシ(Sorghum halepense)、シロアカザ(Chenopodium album)、マルバルコウ(Ipomoea coccinea)、ショクヨウガヤツリ(Cyperus esculentus)、アオゲイトウ(Amaranthus retroflexus)、ブタクサ(Ambrosia elatior)、ダイズ(Glycine max)、イヌビエ(Echinochloa crus-galli)、ナタネ(Brassica napus)、ウォーターヘンプ(waterhemp)(コモンウォーターヘンプ、Amaranthus rudis)、オオホナガアオゲイトウ(Amaranthus palmeri)、ホウキギ(Kochia scoparia)、カラスムギ(Avena fatua)、スリナムグラス(surinam grass)(Brachiaria decumbens)、セイヨウヌカボ(windgrass)(Apera spica-venti)、ショウジョウソウモドキ(poinsettia、wild)(Euphorbia heterophylla)及びイチビ(Abutilon theophrasti)から選択される植物種の種をシルトローム土中に植えて、界面活性剤を含む非植物毒性溶媒混合物に製剤化された試験化学物質を用いて発生前処理した。
ノスズメノテッポウ(Alopecurus myosuroides)、ヤエムグラ(Galium aparine)、ホウキギ(Kochia scoparia)、ナタネ(Brassica napus)、春播オオムギ(Hordeum vulgare)、春播コムギ(Triticum aestivum)、カラスムギ(Avena fatua)、秋播オオムギ(Hordeum vulgare)及び秋播コムギ(Triticum aestivum)から選択される植物種の種子を、シルトローム土中に植えて、界面活性剤を含む非植物毒性溶媒混合物で製剤化された試験化学物質を用いて発生前処理した。
トウモロコシ(Zea mays)、ダイズ (Glycine max)、イチビ(Abutilon theophrasti)、シロアカザ(Chenopodium album)、ショウジョウソウモドキ(Euphorbia heterophylla)、オオホナガアオゲイトウ(Amaranthus palmeri)、ウォーターヘンプ(コモンウォーターヘンプ、Amaranthus rudis)、スリナムグラス(Brachiaria decumbens)、オニメヒシバ(Digitaria sanguinalis)、メヒシバ、ブラジル(Digitaria horizontalis)、オオクサキビ(Panicum dichotomiflorum)、アキノエノコログサ(Setaria faberii)、エノコログサ(Setaria viridis)、オヒシバ(Eleusine indica)、セイバンモロコシ(Sorghum halepense)、ブタクサ(Ambrosia elatior)、イヌビエ(Echinochloa crus-galli)、シンクリノイガ(sandbur)(サザンサンドバー(southern sandbur)、Cenchrus echinatus)、キンゴジカ(Sida rhombifolia)、ネズミムギ(Lolium multiflorum)、バージニアツユクサ(Virginia (VA) dayflower、Commelina virginica)、セイヨウヒルガオ(Convolvulus arvensis)、マルバルコウ(Ipomoea coccinea)、ヒメムカシヨモギ (Conyza canadensis)、ホウキギ(Kochia scoparia)、ショクヨウガヤツリ(Cyperus esculentus)及びコセンダングサ(hairy beggarticks)(Bidens pilosa)から選択される植物種の種子を、シルトローム土中に植えて、界面活性剤を含む非植物毒性溶媒混合物中で製剤化された試験化学物質を用いて発生前処理した。
一評定あたり3つのプラスチック鉢(直径約16cm)を、35:50:15の比の砂、シルト及び粘土並びに2.6%有機物を含む殺菌Tamaシルトローム土で部分的に満たした。3つの鉢のそれぞれについての別々の種播きは以下のとおりであった。コナギ(Monochoria vaginalis)、タマガヤツリ(Cyperus difformis)及びホソバヒメミソハギ(purple redstem、Ammannia coccinea)の米国からの種子を、各評定について1つの16cm鉢に植えた。コゴメガヤツリ(Cyperus iria)、オニアゼガヤ(bearded sprangletop、Leptochloa fascicularis)、1束の9又は10の湛水直播イネ苗(イネ、W.S.Jap、Oryza sativa cv.「Japonica-M202」又はイネ、W.S.Ind、「Indica」)、及び2束の3又は4つの移植イネ苗(Oryza sativa cv.「Japonica-M202」)の米国からの種子を、各評定について1つの16cm鉢に植えた。イヌビエ(Echinochloa crus-galli)、及びタイヌビエ(Echinochloa oryzicola)の米国からの種子を各評定について1つの16cm鉢に植えた。
この試験は、化合物番号20と(b15C1)との混合物のいくつかの植物種に対する効果を評価した。トウモロコシ(ZEAMD;Zea mays、cv.「Pioneer 1184」)、ダイズ(GLXMA;Glycine max、cv.Pioneer 35T58)、アキノエノコログサ(SETFA;Setaria faberi)、イヌビエ(ECHCG;Echinochloa crus-galli)、オニメヒシバ(DIGSA;Digitaria sanguinalis)、オオホナガアオゲイトウ(AMAPA;Amaranthus palmeri)、コモンウォーターヘンプ(AMATU;Amaranthus rudis)、及びブタクサ(AMBEL;Ambrosia artemisiifolia)から選択される植物の種子を、Tamaシルトローム土を含有する鉢に植え、そして界面活性剤を含む非植物毒性溶媒混合物中で製剤化された試験化学物質を使用して有向土壌スプレーを用いて発生前処理した。
この試験は、化合物番号20とアトラジン又はグリホサートとの混合物のいくつかの植物種に対する効果を評価した。トウモロコシ(ZEAMD;Zea mays、cv.「Pioneer 1184」)、ダイズ(GLXMA;Glycine max、cv.Pioneer 35T58)、アキノエノコログサ(SETFA;Setaria faberi)、スリナムグラス(BRADC;Brachiaria decumbens)、オオクサキビ(PANDI;Panicum dichotomiflorum)、イチビ(ABUTH;Abutilon threophrasti)、ヒメムカシヨモギ(mare’s tail)(ERICA;Conyza canadensis)、イヌビエ(ECHCG;Echinochloa crus-galli)、オニメヒシバ(DIGSA;Digitaria sanguinalis)、オオホナガアオゲイトウ(AMAPA;Amaranthus palmeri)、コモンウォーターヘンプ(AMATU;Amaranthus rudis)、アメリカイヌホオズキ(E.black nightshade)(SOLPT;Solanum ptycanthum)、及びブタクサ(AMBEL;Ambrosia artemisiifolia)から選択される植物種の種子を、スファグナムピートモス、バーミキュライト、湿潤剤及び開始栄養剤を含むRedi-Earth(R)栽培用媒体(Scotts Company、14111 Scottslawn Road、Marysville、Ohio 43041)を含有する鉢に植え、そして界面活性剤を含む非植物毒性溶媒混合物中で製剤化された試験化学物質を使用して発生後処理した。発生後処理のために植物は高さ2~10cmの範囲に及び、1~2葉期であった。処理された植物及び未処理の対照を温室に約14日間維持し、その期間の後、全ての植物を未処理対照と比較し、そして損傷について視覚的に評価した。表H1及びH2にまとめられている植物応答評定は0~100のスケールに基づき、0は効果無しであり、そして100は完全な対照である。ダッシュ記号(-)の応答は試験結果無しを意味する。試験結果を4回の繰り返しの平均として示す。
この試験は、化合物番号20とサフルフェナシル又はピロキサスルホンとの混合物のいくつかの植物種に対する効果を評価した。トウモロコシ(ZEAMD;Zea mays、cv.「Pioneer 1184」)、ダイズ(GLXMA;Glycine max、cv.Pioneer 35T58)、アキノエノコログサ(SETFA;Setaria faberi)、オオホナガアオゲイトウ(AMAPA;Amaranthus palmeri)、コモンウォーターヘンプ(AMATU;Amaranthus rudis)、ヒメムカシヨモギ(ERICA;Conyza canadensis)、及びブタクサ(AMBEL;Ambrosia artemisiifolia)から選択された植物種の種子を、Tamaシルトローム土を含有する鉢に植え、そして界面活性剤を含む非植物毒性溶媒混合物中で製剤化された試験化学物質を使用して有向土壌スプレーを用いて発生前処理した。
この試験は、化合物番号20と(b15C2)との混合物のいくつかの植物種に対する効果を評価した。トウモロコシ (ZEAMD;Zea mays、cv.「Pioneer 1184」)、ダイズ(GLXMA;Glycine max、cv.Pioneer 35T58)、アキノエノコログサ(SETFA;Setaria faberi)、オオホナガアオゲイトウ(AMAPA;Amaranthus palmeri)、コモンウォーターヘンプ(AMATU;Amaranthus rudis)、ヒメムカシヨモギ(ERICA;Conyza canadensis)、及びブタクサ(AMBEL;Ambrosia artemisiifolia)から選択される植物種の種子を、Tamaシルトローム土を含有する鉢に植え、そして界面活性剤を含む非植物毒性溶媒混合物中で製剤化された試験化学物質を使用して有向土壌スプレーを用いて発生前処理した。
この試験は、化合物番号20とメトリブジン又はリムスルフロンとの混合物のいくつかの植物種に対する効果を評価した。トウモロコシ(ZEAMD;Zea mays、cv.「Pioneer 1184」)、ダイズ(GLXMA;Glycine max、cv.Pioneer 35T58)、アキノエノコログサ(SETFA;Setaria faberi)、オオホナガアオゲイトウ(AMAPA;Amaranthus palmeri)、コモンウォーターヘンプ(AMATU;Amaranthus rudis)、ヒメムカシヨモギ(ERICA;Conyza canadensis)、及びブタクサ(AMBEL;Ambrosia artemisiifolia)から選択される植物種の種子を、Tamaシルトローム土を含有する鉢に植え、そして界面活性剤を含む非植物毒性溶媒混合物中で製剤化された試験化学物質を使用して有向土壌スプレーを用いて発生前処理した。
この試験は、化合物番号20とベノキサコール、イソオキサジフェン-エチル、又はクロキントセット-メキシルとの混合物のいくつかの植物種に対する効果を評価した。トウモロコシ(ZEAMD;Zea mays、cv.「Pioneer 1184」)、ダイズ(GLXMA;Glycine max、cv.Pioneer 35T58)、秋播コムギ(TRZAW;Triticum aetivum、cv.Arezzo)、イネ(ORYSS;Oryza sativa、cv.M202)、及びアキノエノコログサ(SETFA;Setaria faberi)から選択される植物種の種子を、スファグナムピートモス、バーミキュライト、湿潤剤及び開始栄養剤を含むRedi-Earth(R)栽培用媒体(Scotts Company、14111 Scottslawn Road、Marysville、Ohio 43041)を含有する鉢に植え、そして界面活性剤を含む非植物毒性溶媒混合物中で製剤化された試験化学物質を使用して発生後処理した。発生後処理のために植物は高さ7~10cmの範囲に及び、1~2葉期であった。処理された植物及び未処理の対照を温室に約14日間維持し、その期間の後、全ての植物を未処理対照と比較し、そして損傷について視覚的に評価した。表L1~L3にまとめられている植物応答評定は0~100のスケールに基づき、0は効果無しであり、そして100は完全な対照である。ダッシュ記号(-)の応答は試験結果無しを意味する。試験結果を4回の繰り返しの平均として示す。
この試験は、化合物番号20とイソオキサジフェン-エチル、又はクロキントセット-メキシル、又はメフェンピル-ジエチルとの混合物のいくつかの植物種に対する効果を評価した。トウモロコシ(ZEAMD;Zea mays、cv.「Pioneer 1184」)、ダイズ(GLXMA;Glycine max、cv.Pioneer 35T58)、秋播コムギ(TRZAW;Triticum aetivum、cv.Arezzo)、秋播オオムギ(HORVW;Hordeum vulgare、cv.Boone)、イネ(ORYSS;Oryza sativa、cv.M202)、及びアキノエノコログサ(SETFA;Setaria faberi)から選択される植物種の種子を、スファグナムピートモス、バーミキュライト、湿潤剤及び開始栄養剤を含むRedi-Earth(R)栽培用媒体(Scotts Company、14111 Scottslawn Road、Marysville、Ohio 43041)を含有する鉢に植え、そして界面活性剤を含む非植物毒性溶媒混合物中で製剤化された試験化学物質を使用して発生後処理した。発生後処理のために植物は高さ7~10cmの範囲に及び、1~2葉期であった。処理された植物及び未処理の対照を温室に約14日間維持し、その期間の後、全ての植物を未処理対照と比較し、そして損傷について視覚的に評価した。表M1~M3にまとめられている植物応答評定は0~100のスケールに基づき、0は効果無しであり、そして100は完全な対照である。ダッシュ記号(-)の応答は試験結果無しを意味する。試験結果を3回の繰り返しの平均として示す。
Claims (13)
- R2はClである、請求項1に記載の化合物。
- R5はCH3である、請求項1又は2に記載の化合物。
- R6はClである、請求項1~3のいずれか1項に記載の化合物。
- 6-クロロ-4-(2,7-ジメチル-1-ナフタレニル)-5-ヒドロキシ-2-メチル-3(2H)-ピリダジノン;
6-クロロ-4-(7-フルオロ-2-メチル-1-ナフタレニル)-5-ヒドロキシ-2-メチル-3(2H)-ピリダジノン;及び
6-クロロ-4-(7-クロロ-2-メチル-1-ナフタレニル)-5-ヒドロキシ-2-メチル-3(2H)-ピリダジノン
からなる群より選択される、請求項1に記載の化合物。 - 請求項1に記載の化合物、並びに界面活性剤、固体希釈剤、及び液体希釈剤からなる群より選択される少なくとも1つの成分を含む、除草剤組成物。
- 請求項1に記載の化合物、他の除草剤及び除草剤薬害軽減剤からなる群より選択される少なくとも1つのさらなる活性成分、並びに界面活性剤、固体希釈剤、及び液体希釈剤からなる群より選択される少なくとも1つの成分を含む、除草剤組成物。
- (a)請求項1に記載の化合物、及び(b)少なくとも1つのさらなる活性成分を含む、除草剤混合物。
- (b)少なくとも1つのさらなる活性成分は、5-クロロ-2-[3-クロロ-2-[3-(ジフルオロメチル)-5-イソオキサゾリル]フェノキシ]-ピリミジン、1-[2-クロロ-6-[(5-クロロ-2-ピリミジニル)オキシ]フェニル]-4,4,4-トリフルオロ-1-ブタノン、2,4-D、アセトクロール、アシフルオフフェン、アトラジン、カルフェントラゾン、クロリムロン、クレトジム、クロマゾン、クロピラリド、クロランスラム-メチル、ジカンバ、ジフルフェニカン、ジメテナミド、ジクワット、フルミオキサジン、フルロキシピル、フルチアセット-メチル、ホメサフェン、グルホシネート、グリホサート、イマゼタピル、イソキサフルトール、ラクトフェン、メソトリオン、メトリブジン、ピロキサスルホン、リムスルフロン、サフルフェナシル、S-メトラクロール、スルフェントラゾン、テンボトリオン、チエンカルバゾン、トルピラレート、トプラメゾン、ベノキサコール、イソキサジフェン-エチル、クロキントセット-メキシル、及びメフェンピル-ジエチルから成る群から選択される、請求項8に記載の除草剤混合物。
- (b)少なくとも1つのさらなる活性成分は、5-クロロ-2-[3-クロロ-2-[3-(ジフルオロメチル)-5-イソオキサゾリル]フェノキシ]-ピリミジン、アトラジン、グリホサート、サフルフェナシル、ピロキサスルホン、1-[2-クロロ-6-[(5-クロロ-2-ピリミジニル)オキシ]フェニル]-4,4,4-トリフルオロ-1-ブタノン、メトリブジン、及びリムスルフロンから成る群から選択される、請求項9に記載の除草剤混合物。
- (b)少なくとも1つのさらなる活性成分は、ベノキサコール、イソキサジフェン-エチル、クロキントセット-メキシル、及びメフェンピル-ジエチルから成る群から選択される、請求項9に記載の除草剤混合物。
- (b)少なくとも1つのさらなる活性成分は、S-メトラクロール、スルフェントラゾン、クロマゾン、クロリムロン、ホメサフェン、フルミオキサジン、フルロキシピル、2,4-D、イソキサフルトール、ジフルフェニカン、メソトリオン、トプラメゾン、トルピラレート、ジカンバ、カルフェントラゾン、クロピラリド、アセトクロール、及びチエンカルバゾンから成る群から選択される、請求項9に記載の除草剤混合物。
- 望ましくない植生又はその環境を、除草有効量の請求項1の化合物と接触させることを
含む、望ましくない植生の成長を防除するための方法。
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US10349341B2 (en) * | 2014-01-17 | 2019-07-09 | Blackberry Limited | Wireless network service type |
GB202016568D0 (en) | 2020-10-19 | 2020-12-02 | Syngenta Crop Protection Ag | Herbicidal compositions |
JP2023554672A (ja) | 2020-12-22 | 2023-12-28 | エフ エム シー コーポレーション | 置換ピリダジノン除草剤 |
AR125453A1 (es) | 2021-04-27 | 2023-07-19 | Bayer Ag | Piridazinonas sustituidas, sales o n-óxidos de las mismas y su uso como sustancias herbicidamente activas |
TW202321229A (zh) | 2021-08-18 | 2023-06-01 | 美商富曼西公司 | 殺真菌的取代的雜環化合物 |
GB202116307D0 (en) | 2021-11-12 | 2021-12-29 | Syngenta Crop Protection Ag | Herbicide resistance |
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- 2019-09-26 KR KR1020217011978A patent/KR20210065979A/ko not_active Application Discontinuation
- 2019-09-26 CN CN201980077703.5A patent/CN113166075A/zh active Pending
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US20220041560A1 (en) | 2022-02-10 |
TW202012376A (zh) | 2020-04-01 |
BR112021005787A2 (pt) | 2021-06-29 |
CN113166075A (zh) | 2021-07-23 |
KR20210065979A (ko) | 2021-06-04 |
MX2021003530A (es) | 2021-05-27 |
PE20211219A1 (es) | 2021-07-05 |
CO2021003758A2 (es) | 2021-04-08 |
CA3113063A1 (en) | 2020-04-02 |
SG11202102638WA (en) | 2021-04-29 |
TWI835870B (zh) | 2024-03-21 |
EP3856723A1 (en) | 2021-08-04 |
WO2020069057A1 (en) | 2020-04-02 |
CL2021000694A1 (es) | 2021-09-24 |
JP2022501396A (ja) | 2022-01-06 |
IL281496A (en) | 2021-04-29 |
EA202190848A1 (ru) | 2021-08-17 |
AR116556A1 (es) | 2021-05-19 |
AU2019347855A1 (en) | 2021-04-08 |
PH12021550651A1 (en) | 2022-02-14 |
UY38392A (es) | 2020-04-30 |
AU2019347855A2 (en) | 2022-09-22 |
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