JP2018521958A - 除草剤としてのブチロラクトン - Google Patents
除草剤としてのブチロラクトン Download PDFInfo
- Publication number
- JP2018521958A JP2018521958A JP2017556231A JP2017556231A JP2018521958A JP 2018521958 A JP2018521958 A JP 2018521958A JP 2017556231 A JP2017556231 A JP 2017556231A JP 2017556231 A JP2017556231 A JP 2017556231A JP 2018521958 A JP2018521958 A JP 2018521958A
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- JP
- Japan
- Prior art keywords
- ring
- alkyl
- independently
- compound
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004009 herbicide Substances 0.000 title claims description 45
- 230000002363 herbicidal effect Effects 0.000 title claims description 33
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 title description 10
- 229930188620 butyrolactone Natural products 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 223
- 239000000203 mixture Substances 0.000 claims abstract description 102
- 238000000034 method Methods 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 15
- -1 hydroxy, amino Chemical group 0.000 claims description 178
- 125000001424 substituent group Chemical group 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000004480 active ingredient Substances 0.000 claims description 28
- 239000003085 diluting agent Substances 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 239000007788 liquid Substances 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000004122 cyclic group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 150000001721 carbon Chemical group 0.000 claims description 15
- 230000012010 growth Effects 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 9
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 5
- 125000006660 (C3-C4) halocycloalkyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 5
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 5
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 5
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 5
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 3
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 3
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006815 (C4-C10) cycloalkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000006781 (C4-C10) cycloalkylcarbonyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 230000006315 carbonylation Effects 0.000 claims description 2
- 238000005810 carbonylation reaction Methods 0.000 claims description 2
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 2
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 72
- 239000003112 inhibitor Substances 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 27
- 238000009472 formulation Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 14
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 150000002148 esters Chemical group 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- 229930192334 Auxin Natural products 0.000 description 10
- 239000002363 auxin Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 240000008042 Zea mays Species 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 235000005822 corn Nutrition 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
- 101150065749 Churc1 gene Proteins 0.000 description 7
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
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- 150000001298 alcohols Chemical class 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
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- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
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- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical class COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
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Abstract
Description
(式中、
Q1は、各環もしくは環系が、R7から独立して選択される5個までの置換基で任意選択的に置換されたフェニル環もしくはナフタレニル環系;または、各環もしくは環系が、炭素原子ならびに2個までのO原子、2個までのS原子および4個までのN原子から独立して選択される1〜4個のヘテロ原子から選択される環員を含有する5〜6員の完全不飽和複素環または8〜10員の芳香族複素環式二環系であり、ここで3個までの炭素環員はC(=O)およびC(=S)から独立して選択され、硫黄原子環員は、各環もしくは環系が炭素原子環員上のR7から独立して選択され、窒素原子環員上のR9から選択される5個までの置換基で任意選択的に置換されたS(=O)u(=NR8)vから独立して選択される;
Q2は、各環もしくは環系が、R10から独立して選択される5個までの置換基で任意選択的に置換されたフェニル環もしくはナフタレニル環系;または、各環もしくは環系が、炭素原子ならびに2個までのO原子、2個までのS原子および4個までのN原子から独立して選択される1〜4個のヘテロ原子から選択される環員を含有する5〜6員の完全不飽和複素環または8〜10員の芳香族複素環式二環系であり、ここで3個までの炭素環員はC(=O)およびC(=S)から独立して選択され、硫黄原子環員は、各環もしくは環系が、炭素原子環員上のR10から独立して選択され、および窒素原子環員上のR11から選択される8個までの置換基で任意選択的に置換されたS(=O)u(=NR8)vから独立して選択される;
Y1およびY2は、それぞれ独立してO、SもしくはNR6であり;
R1は、H、ヒドロキシ、アミノ、C1〜C6アルキル、C1〜C6ハロアルキル、C2〜C6アルケニル、C3〜C6アルキニル、C2〜C8アルコキシアルキル、C2〜C8ハロアルコキシアルキル、C2〜C8アルキルチオアルキル、C2〜C8アルキルスルフィニルアルキル、C2〜C8アルキルスルホニルアルキル、C2〜C8アルキルカルボニル、C2〜C8ハロアルキルカルボニル、C4〜C10シクロアルキルカルボニル、C2〜C8アルコキシカルボニル、C2〜C8ハロアルコキシカルボニル、C4〜C10シクロアルコキシカルボニル、C2〜C8アルキルアミノカルボニル、C3〜C10ジアルキルアミノカルボニル、C4〜C10シクロアルキルアミノカルボニル、C1〜C6アルコキシ、C1〜C6アルキルチオ、C1〜C6ハロアルキルチオ、C3〜C8シクロアルキルチオ、C1〜C6アルキルスルフィニル、C1〜C6ハロアルキルスルフィニル、C3〜C8シクロアルキルスルフィニル、C1〜C6アルキルスルホニル、C1〜C6ハロアルキルスルホニル、C3〜C8シクロアルキルスルホニル、C1〜C6アルキルアミノスルホニル、C2〜C8ジアルキルアミノスルホニル、C3〜C10トリアルキルシリルもしくはG1であり;
R2およびR3は、それぞれ独立してH、ハロゲン、ヒドロキシ、C1〜C4アルキル、C1〜C4ハロアルキルもしくはC1〜C4アルコキシであり;または
R2およびR3は、それらが結合する炭素原子と一緒にされてC3〜C7シクロアルキル環を形成する;
R4およびR5は、それぞれ独立してH、ハロゲン、ヒドロキシ、C1〜C4アルキルもしくはC1〜C4アルコキシであり;
各R6は、独立してH、シアノ、C1〜C4アルキル、C1〜C4ハロアルキル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、−(C=O)CH3もしくは−(C=O)CF3であり;
各R8は、独立してH、シアノ、C2〜C3アルキルカルボニルもしくはC2〜C3ハロアルキルカルボニルであり;
各R7およびR10は、独立してハロゲン、シアノ、ニトロ、C1〜C8アルキル、C1〜C4シアノアルキル、C1〜C4シアノアルコキシ、C1〜C8ハロアルキル、C1〜C8ニトロアルキル、C2〜C8アルケニル、C2〜C8ハロアルケニル、C2〜C8ニトロアルケニル、C2〜C8アルキニル、C2〜C8ハロアルキニル、C4〜C10シクロアルキルアルキル、C4〜C10ハロシクロアルキルアルキル、C5〜C12アルキルシクロアルキルアルキル、C5〜C12シクロアルキルアルケニル、C5〜C12シクロアルキルアルキニル、C3〜C8シクロアルキル、C3〜C8ハロシクロアルキル、C4〜C10アルキルシクロアルキル、C6〜C12シクロアルキルシクロアルキル、C3〜C8シクロアルケニル、C3〜C8ハロシクロアルケニル、C2〜C8アルコキシアルキル、C2〜C8ハロアルコキシアルキル、C4〜C10シクロアルコキシアルキル、C3〜C10アルコキシアルコキシアルキル、C2〜C8アルキルチオアルキル、C2〜C8アルキルスルフィニルアルキル、C2〜C8アルキルスルホニルアルキル、C2〜C8アルキルアミノアルキル、C2〜C8ハロアルキルアミノアルキル、C4〜C10シクロアルキルアミノアルキル、C3〜C10ジアルキルアミノアルキル、−CHO、C2〜C8アルキルカルボニル、C2〜C8ハロアルキルカルボニル、C4〜C10シクロアルキルカルボニル、−C(=O)OH、C2〜C8アルコキシカルボニル、C2〜C8ハロアルコキシカルボニル、C4〜C10シクロアルコキシカルボニル、C5〜C12シクロアルキルアルコキシカルボニル、−C(=O)NH2、C2〜C8アルキルアミノカルボニル、C4〜C10シクロアルキルアミノカルボニル、C3〜C10ジアルキルアミノカルボニル、C1〜C8アルコキシ、C1〜C8ハロアルコキシ、C2〜C8アルコキシアルコキシ、C2〜C8ハロアルコキシアルコキシ、C2〜C8アルケニルオキシ、C2〜C8ハロアルケニルオキシ、C3〜C8アルキニルオキシ、C3〜C8ハロアルキニルオキシ、C3〜C8シクロアルコキシ、C3〜C8ハロシクロアルコキシ、C4〜C10シクロアルキルアルコキシ、C3〜C10アルキルカルボニルアルコキシ、C2〜C8アルキルカルボニルオキシ、C2〜C8ハロアルキルカルボニルオキシ、C4〜C10シクロアルキルカルボニルオキシ、C1〜C8アルキルスルホニルオキシ、C1〜C8ハロアルキルスルホニルオキシ、C1〜C8アルキルチオ、C1〜C8ハロアルキルチオ、C3〜C8シクロアルキルチオ、C1〜C8アルキルスルフィニル、C1〜C8ハロアルキルスルフィニル、C1〜C8アルキルスルホニル、C1〜C8ハロアルキルスルホニル、C3〜C8シクロアルキルスルホニル、ホルミルアミノ、C2〜C8アルキルカルボニルアミノ、C2〜C8ハロアルキルカルボニルアミノ、C2〜C8アルコキシカルボニルアミノ、C1〜C6アルキルスルホニルアミノ、C1〜C6ハロアルキルスルホニルアミノ、−SF5、−SCN、SO2NH2、C3〜C12トリアルキルシリル、C4〜C12トリアルキルシリルアルキル、C4〜C12トリアルキルシリルアルコキシもしくはG2であり;または
2つの隣接R7は、それらが結合する炭素原子と一緒にされてC3〜C7シクロアルキル環を形成する;または
2つの隣接R10は、それらが結合する炭素原子と一緒にされてC3〜C7シクロアルキル環を形成する;
各R9およびR11は、独立してシアノ、C1〜C3アルキル、C2〜C3アルケニル、C2〜C3アルキニル、C3〜C6シクロアルキル、C2〜C3アルコキシアルキル、C1〜C3アルコキシ、C2〜C3アルキルカルボニル、C2〜C3アルコキシカルボニル、C2〜C3アルキルアミノアルキルもしくはC3〜C4ジアルキルアミノアルキルであり;
各G1は、独立してフェニル、フェニルメチル(すなわち、ベンジル)、ピリジニルメチル、フェニルカルボニル(すなわち、ベンゾイル)、フェニルカルボニルアルキル(C1〜C4アルキル)、フェノキシ、フェニルエチニル、フェニルスルホニル;またはそれぞれが環員上でR12から独立して選択される5個までの置換基で任意選択的に置換された5もしくは6員の芳香族複素環であり;
各G2は、独立してフェニル、フェニルメチル(すなわち、ベンジル)、ピリジニルメチル、フェニルカルボニル(すなわち、ベンゾイル)、フェニルカルボニル(C1〜C4アルキル)、フェノキシ、フェニルエチニル、フェニルスルホニル、ピリジニルオキシ;またはそれぞれが環員上でR13から独立して選択される5個までの置換基で任意選択的に置換された5もしくは6員の芳香族複素環であり;
各R12およびR13は、独立してハロゲン、シアノ、ヒドロキシ、アミノ、ニトロ、−CHO、−C(=O)OH、−C(=O)NH2、−SO2NH2、C1〜C6アルキル、C1〜C6ハロアルキル、C2〜C6アルケニル、C2〜C6アルキニル、C2〜C8アルキルカルボニル、C2〜C8ハロアルキルカルボニル、C2〜C8アルコキシカルボニル、C4〜C10シクロアルコキシカルボニル、C5〜C12シクロアルキルアルコキシカルボニル、C2〜C8アルキルアミノカルボニル、C3〜C10ジアルキルアミノカルボニル、C1〜C6アルコキシ、C1〜C6ハロアルコキシ、C2〜C8アルキルカルボニルオキシ、C1〜C6アルキルチオ、C1〜C6ハロアルキルチオ、C1〜C6アルキルスルフィニル、C1〜C6ハロアルキルスルフィニル、C1〜C6アルキルスルホニル、C1〜C6ハロアルキルスルホニル、C1〜C6アルキルアミノスルホニル、C2〜C8ジアルキルアミノスルホニル、C3〜C10トリアルキルシリル、C1〜C6アルキルアミノ、C2〜C8ジアルキルアミノ、C2〜C8アルキルカルボニルアミノ、C1〜C6アルキルスルホニルアミノ、フェニル、ピリジニルもしくはチエニルであり;および
各uおよびvは、uおよびvの合計が0、1もしくは2であることを前提に、S(=O)u(=NR8)vの各例では、独立して0、1もしくは2である)の化合物、それらを含有する農業用組成物および除草剤としてのそれらの使用に向けられる。
各R7およびR10は、独立してハロゲン、シアノ、ニトロ、C1〜C4アルキル、C1〜C4ハロアルキル、C2〜C4アルケニル、C2〜C4ハロアルケニル C2〜C4アルキニル、C2〜C4ハロアルキニル、C1〜C4ニトロアルキル、C2〜C4ニトロアルケニル、C2〜C4アルコキシアルキル、C〜C4ハロアルコキシアルキル、C3〜C4シクロアルキル、C3〜C4ハロシクロアルキル、シクロプロピルメチル、メチルシクロプロピル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C2〜C4アルケニルオキシ、C2〜C4ハロアルケニルオキシ、C3〜C4アルキニルオキシ、C3〜C4ハロアルキニルオキシ、C3〜C4シクロアルコキシ、C1〜C4アルキルチオ、C1〜C4ハロアルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4ハロアルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4ハロアルキルスルホニル、ヒドロキシ、ホルミル、C2〜C4アルキルカルボニル、C2〜C4アルキルカルボニルオキシ、C1〜C4アルキルスルホニルオキシ、C1〜C4ハロアルキルスルホニルオキシ、アミノ、C1〜C4アルキルアミノ、C2〜C4ジアルキルアミノ、ホルミルアミノ、C2〜C4アルキルカルボニルアミノ、−SF5、−SCN、C3〜C4トリアルキルシリル、トリメチルシリルメチルもしくはトリメチルシリルメトキシである;および
各R4およびR11は、独立してC1〜C2アルキルもしくはC2〜C3アルコキシカルボニルである)の化合物。
Y1は、Oであり;
Y2は、Oであり;
R1は、Hであり;
R2は、Hであり;
R3は、Hであり;
R4は、Hであり;および
R5は、Hである)の化合物。
Q1は、R7から独立して選択される1〜3個の置換基で置換されたフェニル環であり;および
Q2は、R10から独立して選択される1〜3個の置換基で置換されたフェニル環である)の化合物。
各R7は、独立してハロゲン、シアノ、C1〜C4アルキル、C1〜C4ハロアルキル、C1〜C4アルコキシもしくはC1〜C4ハロアルコキシであり;および
各R10は、独立してハロゲン、シアノ、C1〜C4アルキル、C1〜C4ハロアルキルもしくはC1〜C4アルキルスルホニルである)の化合物。
Q1は、パラ位でR7から選択される1個の置換基で置換された、またはR7から独立して選択される、1個の置換基はパラ位にあり、他方の置換基はメタ位にある2個の置換基で置換されたフェニル環であり;および
Q2は、パラ位でR10から選択される1個の置換基で置換された、またはR10から独立して選択される、1個の置換基はオルト位にあり、他方の置換基は隣接メタ位にある2個の置換基で置換されたフェニル環である)の化合物。
各R7は、独立してFもしくはCF3であり;および
各R10は、Fである)の化合物。
Y1は、Oであり;
Y2は、Oであり;
R1は、Hであり;
R2は、Hであり;
R3は、Hであり;
R4は、Hであり;および
R5は、HまたはCH3である)の化合物。
4−(4−フルオロフェニル)テトラヒドロ−2−オキソ−N−[2−(トリフルオロメチル)フェニル)]−3−フランカルボキサミド;
(3R,4S)−4−(4−フルオロフェニル)テトラヒドロ−2−オキソ−N−[2−(トリフルオロメチル)フェニル)]−3−フランカルボキサミド;および
(3S,4R)−4−(4−フルオロフェニル)テトラヒドロ−2−オキソ−N−[2−(トリフルオロメチル)フェニル)]−3−フランカルボキサミドからなる群から選択される式1の化合物が含まれる。
(式中、Rd1はH、ClもしくはCF3であり;Rd2はH、ClもしくはBrであり;Rd3はHもしくはClであり;Rd4はH、ClもしくはCF3であり;Rd5はCH3、CH2CH3もしくはCH2CHF2であり;および、Rd6はOHもしくは−OC(=O)−i−Prであり;および、Re1はH、F、Cl、CH3もしくはCH2CH3であり;Re2はHもしくはCF3であり;Re3はH、CH3もしくはCH2CH3であり;Re4はH、FもしくはBrであり;Re5はCl、CH3、CF3、OCF3もしくはCH2CH3であり;Re6はH、CH3、CH2CHF2もしくはC≡CHであり;Re7はOH、−OC(=O)Et、−OC(=O)−i−Prもしくは−OC(=O)−t−Buであり;およびAe8はNもしくはCHである)の化合物が挙げられる。
4−(4−フルオロフェニル)テトラヒドロ−2−オキソ−N−[2−(トリフルオロメチル)フェニル)]−3−フランカルボキサミド(化合物6)の調製
工程A:4−(4−フルオロフェニル)テトラヒドロ−2−オキソ−3−フランカルボン酸エチルエステルの調製
250mLの二口丸底フラスコにエタノール(60mL)中のナトリウム金属(0.99g、0.043モル)を加え、次にマロン酸ジエチル(6.6g、0.041モル)を室温で緩徐に加えた。反応混合物を室温で15分間撹拌し、次に温度を40℃へ上昇させ、この反応混合物に2時間かけて2−(4−フルオロフェニル)オキシラン(5.0g、0.036mmol)を緩徐に加えた。次に反応混合液を次に室温で18時間撹拌した。反応の進行は、TLC分析によって監視した。反応の完了後、反応混合物は1Mの水性塩酸を使用して中性化し、次に残渣に濃縮した。生じた残渣を次に水で希釈し、次に酢酸エチルで(3×300mL)抽出した。結合有機層を水で洗浄し、無水Na2SO4の上方に通して乾燥させ、減圧下で濃縮すると粗化合物が得られた。これを20%の酢酸エチル:石油エーテルを使用するカラムクロマトグラフィーによって精製すると、無色液体として工程Aの標題化合物(3.0g)が得られた。
1H NMR(DMSO−d6)δ 7.48−7.44(m,2H),7.23−7.19(t,J=8.8Hz,2H),4.68−4.66(t,J=7.6Hz,1H),4.22−4.19(m,2H),4.17(m,1H),4.15−4.11(q,2H),1.17−1.14(t,3H).
水(13mL)中の工程Aからの化合物の溶液(1.3g、5.158mmol)に水酸化カリウム(1.73g、30.957mmol)を加え、この反応混合物を室温で2時間撹拌した。反応の進行は、TLC分析によって監視した。反応の完了後、反応混合物を0℃へ冷却し、濃塩酸を加え、生じた混合物を15分間撹拌した。沈降物を濾過すると、138〜140℃で溶融する白色固体として工程Bの標題化合物(750mg)が得られた。
1H NMR(DMSO−d6)δ 13.2(s,1H),7.46−7.45(m,2H),7.44−7.21(t,2H),4.67−4.63(t,J=7.6Hz,1H),4.19−4.01(m,3H).
N,N−ジメチルホルムアミド(3mL)中の工程Bからの化合物の溶液(200mg、0.892mmol)にN,N−ジイソプロピルエチルアミン(138mg、1.071mmol)、次にHATU[1−[ビス(ジメチルアミノ)メチレン]−1H−1,2,3−トリアゾロ[4,5−b]ピリジニウム3−オキシドヘキサフルオロホスフェート](408mg、1.071mmol)および2−(トリフルオロメチル)アニリン(99mg、0.892mmol)を加えた。この反応混合物を室温で6時間撹拌した。反応の進行は、薄層クロマトグラフィー分析によって監視した。反応の完了後、反応混合物を水(15mL)中に注入し、酢酸エチル(3×10mL)で抽出した。結合有機層を水、次に塩水溶液で洗浄し、無水Na2SO4の上方に通して乾燥させ、減圧下で濃縮すると粗化合物が得られた。これを30%の酢酸エチル:石油エーテルを使用するカラムクロマトグラフィーによって精製すると、144〜146℃で溶融する白色固体として実施例1の索引表Aの標題化合物6(100mg)が得られた。
1H NMR(DMSO−d6)δ 10.08(s,1H),7.73−7.66(m,2H),7.47−7.43(m,4H),7.24−7.20(t,2H),4.74−4.70(t,J=7.2Hz,1H),4.21−4.19(m,3H).
本開示は、さらに表12〜20を含むが、各表は、構造が上記の表11の構造と取り換えられることを除いて、上記の表2〜10と同一方法で構成されている。
本開示は、さらに表22〜30を含むが、各表は、構造が上記の表21の構造と取り換えられることを除いて、上記の表2〜10と同一方法で構成されている。
本開示は、さらに表32〜40を含むが、各表は、構造が上記の表31の構造と取り換えられることを除いて、上記の表2〜10と同一方法で構成されている。
液体希釈剤には、さらにアルキル化(例えば、メチル化、エチル化、ブチル化)脂肪酸が含まれるが、このとき脂肪酸は、植物および動物由来のグリセロールエステルの加水分解によって入手されてよく、蒸留によって精製することができる。典型的な液体希釈剤は、Marsden,Solvents Guide,2nd Ed.,Interscience,New York,1950に記載されている。
試験A
イヌビエ(エキノクロア・クルスガリ(Echinochloa crus−galli、メヒシバ(オニメヒシバ、ジギタリア・サングイナリス(Digitaria sanguinalis))、ホウキギ(ニワクサ(Kochia scoparia))、ブタクサ(ブタクサ(common ragweed、アンブローシア・エラチオール(Ambrosia elatior))、アサガオ(イポメア種(Ipomoea spp.))、ベルベットリーフ(イチビ(Abutilon theophrasti))、イタリアン・ライグラス(イタリアン・ライグラス(Italian ryegrass)、ロリウム・マルチフロラム(Lolium multiflorum))、アキノエノコログサ(アキノエノコログサ(giant foxtail)、セタリア・ファベリイ(Setaria faberii))、コムギ(トリチクム・アエスチブム(Triticum aestivum))、コーン(ジー・メイズ(Zea mays))およびアカザ(アオゲイトウ(Amaranthus retroflexus))から選択される植物種の種子をローム土壌と砂とのブレンドに植え、界面活性剤を含む非植物毒性溶媒混合物中で処方した試験薬剤を使用して直接土壌噴霧で発芽前処理した。
イネ(オリザ・サティバ(Oryza sativa))、カヤツリグサ(スモール・フラワー・アンブレラ・セッジ(small−flower umbrella sedge)、シペルス・ディフォルミス(Cyperus difformis))、アメリカコナギ(ヘテランテラ・リモサ(Heteranthera limosa)およびイヌビエ(エキノクロア・クルスガリ(Echinochloa crus−galli))から選択される、冠水させた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。処理時に、試験ポットを土壌表面から3cm上まで冠水させ、試験化合物を田面水に直接適用することにより処理し、その後は、試験期間中その水深で維持した。処理した植物およびコントロールを温室中で13〜15日間維持し、その後に、すべての種をコントロールと比較して視覚的に評価した。表Bに要約した植物の応答評価は、0〜100のスケールに基づいており、0は効果なしであり、100は完全な防除である。ダッシュ(−)応答は、試験結果が得られなかったことを意味する。
Claims (12)
- 式1:
(式中、
Q1は、各環もしくは環系が、R7から独立して選択される5個までの置換基で任意選択的に置換されたフェニル環もしくはナフタレニル環系;または、各環もしくは環系が、炭素原子ならびに2個までのO原子、2個までのS原子および4個までのN原子から独立して選択される1〜4個のヘテロ原子から選択される環員を含有する5〜6員の完全不飽和複素環または8〜10員の芳香族複素環式二環系であり、ここで3個までの炭素環員はC(=O)およびC(=S)から独立して選択され、硫黄原子環員は、各環もしくは環系が炭素原子環員上のR7から独立して選択され、窒素原子環員上のR9から選択される5個までの置換基で任意選択的に置換されたS(=O)u(=NR8)vから独立して選択される;
Q2は、各環もしくは環系が、R10から独立して選択される5個までの置換基で任意選択的に置換されたフェニル環もしくはナフタレニル環系;または、各環もしくは環系が、炭素原子ならびに2個までのO原子、2個までのS原子および4個までのN原子から独立して選択される1〜4個のヘテロ原子から選択される環員を含有する5〜6員の完全不飽和複素環または8〜10員の芳香族複素環式二環系であり、ここで3個までの炭素環員はC(=O)およびC(=S)から独立して選択され、硫黄原子環員は、各環もしくは環系が、炭素原子環員上のR10から独立して選択され、および窒素原子環員上のR11から選択される8個までの置換基で任意選択的に置換されたS(=O)u(=NR8)vから独立して選択される;
Y1およびY2は、それぞれ独立してO、SもしくはNR6であり;
R1は、H、ヒドロキシ、アミノ、C1〜C6アルキル、C1〜C6ハロアルキル、C2〜C6アルケニル、C3〜C6アルキニル、C2〜C8アルコキシアルキル、C2〜C8ハロアルコキシアルキル、C2〜C8アルキルチオアルキル、C2〜C8アルキルスルフィニルアルキル、C2〜C8アルキルスルホニルアルキル、C2〜C8アルキルカルボニル、C2〜C8ハロアルキルカルボニル、C4〜C10シクロアルキルカルボニル、C2〜C8アルコキシカルボニル、C2〜C8ハロアルコキシカルボニル、C4〜C10シクロアルコキシカルボニル、C2〜C8アルキルアミノカルボニル、C3〜C10ジアルキルアミノカルボニル、C4〜C10シクロアルキルアミノカルボニル、C1〜C6アルコキシ、C1〜C6アルキルチオ、C1〜C6ハロアルキルチオ、C3〜C8シクロアルキルチオ、C1〜C6アルキルスルフィニル、C1〜C6ハロアルキルスルフィニル、C3〜C8シクロアルキルスルフィニル、C1〜C6アルキルスルホニル、C1〜C6ハロアルキルスルホニル、C3〜C8シクロアルキルスルホニル、C1〜C6アルキルアミノスルホニル、C2〜C8ジアルキルアミノスルホニル、C3〜C10トリアルキルシリルもしくはG1であり;
R2およびR3は、それぞれ独立してH、ハロゲン、ヒドロキシ、C1〜C4アルキル、C1〜C4ハロアルキルもしくはC1〜C4アルコキシであり;または
R2およびR3は、それらが結合する炭素原子と一緒にされてC3〜C7シクロアルキル環を形成する;
R4およびR5は、それぞれ独立してH、ハロゲン、ヒドロキシ、C1〜C4アルキルもしくはC1〜C4アルコキシであり;
各R6は、独立してH、シアノ、C1〜C4アルキル、C1〜C4ハロアルキル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、−(C=O)CH3もしくは−(C=O)CF3であり;
各R8は、独立してH、シアノ、C2〜C3アルキルカルボニルもしくはC2〜C3ハロアルキルカルボニルであり;
各R7およびR10は、独立してハロゲン、シアノ、ニトロ、C1〜C8アルキル、C1〜C4シアノアルキル、C1〜C4シアノアルコキシ、C1〜C8ハロアルキル、C1〜C8ニトロアルキル、C2〜C8アルケニル、C2〜C8ハロアルケニル、C2〜C8ニトロアルケニル、C2〜C8アルキニル、C2〜C8ハロアルキニル、C4〜C10シクロアルキルアルキル、C4〜C10ハロシクロアルキルアルキル、C5〜C12アルキルシクロアルキルアルキル、C5〜C12シクロアルキルアルケニル、C5〜C12シクロアルキルアルキニル、C3〜C8シクロアルキル、C3〜C8ハロシクロアルキル、C4〜C10アルキルシクロアルキル、C6〜C12シクロアルキルシクロアルキル、C3〜C8シクロアルケニル、C3〜C8ハロシクロアルケニル、C2〜C8アルコキシアルキル、C2〜C8ハロアルコキシアルキル、C4〜C10シクロアルコキシアルキル、C3〜C10アルコキシアルコキシアルキル、C2〜C8アルキルチオアルキル、C2〜C8アルキルスルフィニルアルキル、C2〜C8アルキルスルホニルアルキル、C2〜C8アルキルアミノアルキル、C2〜C8ハロアルキルアミノアルキル、C4〜C10シクロアルキルアミノアルキル、C3〜C10ジアルキルアミノアルキル、−CHO、C2〜C8アルキルカルボニル、C2〜C8ハロアルキルカルボニル、C4〜C10シクロアルキルカルボニル、−C(=O)OH、C2〜C8アルコキシカルボニル、C2〜C8ハロアルコキシカルボニル、C4〜C10シクロアルコキシカルボニル、C5〜C12シクロアルキルアルコキシカルボニル、−C(=O)NH2、C2〜C8アルキルアミノカルボニル、C4〜C10シクロアルキルアミノカルボニル、C3〜C10ジアルキルアミノカルボニル、C1〜C8アルコキシ、C1〜C8ハロアルコキシ、C2〜C8アルコキシアルコキシ、C2〜C8ハロアルコキシアルコキシ、C2〜C8アルケニルオキシ、C2〜C8ハロアルケニルオキシ、C3〜C8アルキニルオキシ、C3〜C8ハロアルキニルオキシ、C3〜C8シクロアルコキシ、C3〜C8ハロシクロアルコキシ、C4〜C10シクロアルキルアルコキシ、C3〜C10アルキルカルボニルアルコキシ、C2〜C8アルキルカルボニルオキシ、C2〜C8ハロアルキルカルボニルオキシ、C4〜C10シクロアルキルカルボニルオキシ、C1〜C8アルキルスルホニルオキシ、C1〜C8ハロアルキルスルホニルオキシ、C1〜C8アルキルチオ、C1〜C8ハロアルキルチオ、C3〜C8シクロアルキルチオ、C1〜C8アルキルスルフィニル、C1〜C8ハロアルキルスルフィニル、C1〜C8アルキルスルホニル、C1〜C8ハロアルキルスルホニル、C3〜C8シクロアルキルスルホニル、ホルミルアミノ、C2〜C8アルキルカルボニルアミノ、C2〜C8ハロアルキルカルボニルアミノ、C2〜C8アルコキシカルボニルアミノ、C1〜C6アルキルスルホニルアミノ、C1〜C6ハロアルキルスルホニルアミノ、−SF5、−SCN、SO2NH2、C3〜C12トリアルキルシリル、C4〜C12トリアルキルシリルアルキル、C4〜C12トリアルキルシリルアルコキシもしくはG2であり;または
2つの隣接R7は、それらが結合する炭素原子と一緒にされてC3〜C7シクロアルキル環を形成する;または
2つの隣接R10は、それらが結合する炭素原子と一緒にされてC3〜C7シクロアルキル環を形成する;
各R9およびR11は、独立してシアノ、C1〜C3アルキル、C2〜C3アルケニル、C2〜C3アルキニル、C3〜C6シクロアルキル、C2〜C3アルコキシアルキル、C1〜C3アルコキシ、C2〜C3アルキルカルボニル、C2〜C3アルコキシカルボニル、C2〜C3アルキルアミノアルキルもしくはC3〜C4ジアルキルアミノアルキルであり;
各G1は、独立してフェニル、フェニルメチル、ピリジニルメチル、フェニルカルボニル、フェニルカルボニルアルキル(C1〜C4アルキル)、フェノキシ、フェニルエチニル、フェニルスルホニル;またはそれぞれが環員上でR12から独立して選択される5個までの置換基で任意選択的に置換された5もしくは6員の芳香族複素環であり;
各G2は、独立してフェニル、フェニルメチル、ピリジニルメチル、フェニルカルボニル、フェニルカルボニル(C1〜C4アルキル)、フェノキシ、フェニルエチニル、フェニルスルホニル、ピリジニルオキシ;またはそれぞれが環員上でR13から独立して選択される5個までの置換基で任意選択的に置換された5もしくは6員の芳香族複素環であり;
各R12およびR13は、独立してハロゲン、シアノ、ヒドロキシ、アミノ、ニトロ、−CHO、−C(=O)OH、−C(=O)NH2、−SO2NH2、C1〜C6アルキル、C1〜C6ハロアルキル、C2〜C6アルケニル、C2〜C6アルキニル、C2〜C8アルキルカルボニル、C2〜C8ハロアルキルカルボニル、C2〜C8アルコキシカルボニル、C4〜C10シクロアルコキシカルボニル、C5〜C12シクロアルキルアルコキシカルボニル、C2〜C8アルキルアミノカルボニル、C3〜C10ジアルキルアミノカルボニル、C1〜C6アルコキシ、C1〜C6ハロアルコキシ、C2〜C8アルキルカルボニルオキシ、C1〜C6アルキルチオ、C1〜C6ハロアルキルチオ、C1〜C6アルキルスルフィニル、C1〜C6ハロアルキルスルフィニル、C1〜C6アルキルスルホニル、C1〜C6ハロアルキルスルホニル、C1〜C6アルキルアミノスルホニル、C2〜C8ジアルキルアミノスルホニル、C3〜C10トリアルキルシリル、C1〜C6アルキルアミノ、C2〜C8ジアルキルアミノ、C2〜C8アルキルカルボニルアミノ、C1〜C6アルキルスルホニルアミノ、フェニル、ピリジニルもしくはチエニルであり;および
各uおよびvは、uおよびvの合計が0、1もしくは2であることを前提に、S(=O)u(=NR8)vの各例では、独立して0、1もしくは2である)、それらのN−オキシドおよび塩から選択される化合物。 - 式中、
各R7およびR10は、独立してハロゲン、シアノ、ニトロ、C1〜C4アルキル、C1〜C4ハロアルキル、C2〜C4アルケニル、C2〜C4ハロアルケニル C2〜C4アルキニル、C2〜C4ハロアルキニル、C1〜C4ニトロアルキル、C2〜C4ニトロアルケニル、C2〜C4アルコキシアルキル、C2〜C4ハロアルコキシアルキル、C3〜C4シクロアルキル、C3〜C4ハロシクロアルキル、シクロプロピルメチル、メチルシクロプロピル、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C2〜C4アルケニルオキシ、C2〜C4ハロアルケニルオキシ、C3〜C4アルキニルオキシ、C3〜C4ハロアルキニルオキシ、C3〜C4シクロアルコキシ、C1〜C4アルキルチオ、C1〜C4ハロアルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4ハロアルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4ハロアルキルスルホニル、ヒドロキシ、ホルミル、C2〜C4アルキルカルボニル、C2〜C4アルキルカルボニルオキシ、C1〜C4アルキルスルホニルオキシ、C1〜C4ハロアルキルスルホニルオキシ、アミノ、C1〜C4アルキルアミノ、C2〜C4ジアルキルアミノ、ホルミルアミノ、C2〜C4アルキルカルボニルアミノ、−SF5、−SCN、C3〜C4トリアルキルシリル、トリメチルシリルメチルもしくはトリメチルシリルメトキシである;および
各R4およびR11は、独立してC1〜C2アルキルもしくはC2〜C3アルコキシカルボニルである、請求項1に記載の化合物。 - 式中、
Y1は、Oであり;
Y2は、Oであり;
R1は、Hであり;
R2は、Hであり;
R3は、Hであり;
R4は、Hであり;および
R5は、HまたはCH3である、請求項2に記載の化合物。 - 式中、
Q1は、R7から独立して選択される1〜3個の置換基で置換されたフェニル環であり;および
Q2は、R10から独立して選択される1〜3個の置換基で置換されたフェニル環である、請求項3に記載の化合物。 - 式中、
各R7は、独立してハロゲン、シアノ、C1〜C4アルキル、C1〜C4ハロアルキルC1〜C4アルコキシもしくはC1〜C4ハロアルコキシであり;および
各R10は、独立してハロゲン、シアノ、C1〜C4アルキル、C1〜C4ハロアルキルもしくはC1〜C4アルキルスルホニルである、請求項4に記載の化合物。 - 式中、
Q1は、パラ位でR7から選択される1個の置換基で置換された、またはR7から独立して選択される、1個の置換基はパラ位にあり、他方の置換基はメタ位にある2個の置換基で置換されたフェニル環であり;および
Q2は、パラ位でR10から選択される1個の置換基で置換された、またはR10から独立して選択される、1個の置換基はオルト位にあり、他方の置換基は隣接メタ位にある2個の置換基で置換されたフェニル環である、請求項5に記載の化合物。 - 式中、
各R7は、独立してFまたはCF3であり;および
各R10は、Fである、請求項6に記載の化合物。 - 下記の:
4−(4−フルオロフェニル)テトラヒドロ−2−オキソ−N−[2−(トリフルオロメチル)フェニル)]−3−フランカルボキサミド;
(3R,4S)−4−(4−フルオロフェニル)テトラヒドロ−2−オキソ−N−[2−(トリフルオロメチル)フェニル)]−3−フランカルボキサミド;および
(3S,4R)−4−(4−フルオロフェニル)テトラヒドロ−2−オキソ−N−[2−(トリフルオロメチル)フェニル)]−3−フランカルボキサミドからなる群から選択される、請求項1に記載の化合物。 - 請求項1に記載の化合物ならびに界面活性剤、固体希釈剤および液体希釈剤からなる群から選択される少なくとも1つの構成成分を含む除草剤組成物。
- 請求項1に記載の化合物、他の除草剤および除草剤毒性緩和剤からなる群から選択される少なくとも1つの追加の有効成分ならびに界面活性剤、固体希釈剤および液体希釈剤からなる群から選択される少なくとも1つの構成成分を含む除草剤組成物。
- (a)請求項1に記載の化合物、および(b)下記に記載する(b1)〜(b16)から選択される少なくとも1つの追加の有効成分;ならびに(b1)〜(b16)から選択される化合物の塩を含む除草剤混合物。
- 望ましくない植生の成長を防除するための方法であって、植生もしくはその環境を除草剤性有効量の請求項1に記載の化合物と接触させる工程を含む方法。
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