JP2005015390A - Azolidine derivative and herbicide - Google Patents
Azolidine derivative and herbicide Download PDFInfo
- Publication number
- JP2005015390A JP2005015390A JP2003182274A JP2003182274A JP2005015390A JP 2005015390 A JP2005015390 A JP 2005015390A JP 2003182274 A JP2003182274 A JP 2003182274A JP 2003182274 A JP2003182274 A JP 2003182274A JP 2005015390 A JP2005015390 A JP 2005015390A
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- JP
- Japan
- Prior art keywords
- alkyl
- compound
- formula
- chloro
- haloalkyl
- 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.)
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- 239000004009 herbicide Substances 0.000 title claims abstract description 48
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 42
- 150000007982 azolidines Chemical class 0.000 title claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 5
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 73
- -1 chloro, bromo, methyl Chemical group 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 125000005997 bromomethyl group Chemical group 0.000 claims description 3
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract 1
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- 238000004519 manufacturing process Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- 238000005507 spraying Methods 0.000 description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
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- 241000234653 Cyperus Species 0.000 description 3
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- 240000007038 Lindernia dubia Species 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
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- 229940100389 Sulfonylurea Drugs 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
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- 238000000034 method Methods 0.000 description 3
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
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- 239000000454 talc Substances 0.000 description 3
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- 241000208296 Datura Species 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- YXRPHMVUMUKKOS-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine;pyridine Chemical compound C1=CC=NC=C1.CN(C)C1=CC=NC=C1 YXRPHMVUMUKKOS-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IQDUSUMPAWCGJY-UHFFFAOYSA-N pyridine-2,3-dicarbothioic s-acid Chemical compound SC(=O)C1=CC=CN=C1C(S)=O IQDUSUMPAWCGJY-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 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
- 239000010453 quartz Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000002904 solvent Substances 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
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Description
【０００１】
【発明の属する技術分野】
本発明は新規なアゾリジン誘導体及びその除草剤としての利用に関する。
【０００２】
【従来の技術】
ある種のアゾリジン誘導体が除草剤としての作用を示すことは既に知られている（特許文献１〜３、非特許文献１等参照）。
【０００３】
【特許文献１】
ＰＣＴ国際出願 ＷＯ ９５／３３７１９パンフレット
【０００４】
【特許文献２】
ＰＣＴ国際出願 ＷＯ ９７／２０８３８パンフレット
【０００５】
【特許文献３】
ＰＣＴ国際出願 ＷＯ ００／２１９２８パンフレット
【０００６】
【非特許文献１】
Ａｍｅｒｉｃａｎ Ｃｈｅｍｉｃａｌ Ｓｏｃｉｅｔｙ，１８−２９（２００２）
【０００７】
【発明が解決しようとする課題】
しかしながら、除草剤として上記の刊行物に開示されている既知の誘導体は除草剤としての効果及び／又は安全性の点で十分に満足できるものではない。
【０００８】
【課題を解決するための手段】
本発明者らは、除草剤としてより高い効果を有し且つより高い安全性を有する新規有用化合物を創製すべく鋭意研究を行った結果、今回、優れた生物活性を持つ下記式で表される新規なアゾリジン誘導体を見出した。
【０００９】
【化５】
式中、
Ｒ１はハロゲン、アルキル、アルコキシ、ハロアルキル、ハロアルコキシ、ハロアルキルチオ又はハロアルキレンジオキシを示し、
ｍは０、１、２、３、４又は５を示し、
ｍが２、３、４又は５を示すとき、２〜５個のＲ１は同一もしくは相異なり、
Ｒ２はアルキルを示し、
Ｘはアルキリデン、酸素原子又は硫黄原子を示し、そして
Ａは基
【００１１】
【化６】
を示し、ここで
Ｑはアルキルを示し、
Ｑ−ｈａｌはハロアルキルを示し、そして
Ｈａｌはハロゲンを示す。
【００１３】
本発明の上記式（Ｉ）の化合物は、例えば、下記の製法（ａ）によって合成することができる。
製法（ａ）：式
【００１４】
【化７】
式中、Ｒ１、ｍ、Ｒ２及びＸは前記と同義である、
で表される化合物を式
【００１６】
【化８】
式中、Ｍはハロゲン又は水酸基を示し、そして
Ａは前記と同義である、
で表される化合物と反応させる方法。
【００１８】
本発明により提供される式（Ｉ）のアゾリジン誘導体は強力な除草活性を示す。本発明による式（Ｉ）のアゾリジン誘導体は、前記特許文献１に記載された一般式（Ｉ）で示される化合物に概念上包含されるが、該パンフレットに具体的に記載されていない新規化合物である。そして、意外にも、上記特許文献１に具体的に記載されている構造類似の既知の化合物に比して、極めて強力な除草作用を現す。
【００１９】
したがって、本発明の式（Ｉ）のアゾリジン誘導体の除草剤として使用することができる。
【００２０】
本発明の式（Ｉ）のアゾリジン誘導体は、また、後記で具体的に示すとおり、他の除草活性化合物又は薬害軽減剤と混合することにより、混合除草剤組成物として、より一層強力な除草効果ならびに選択性を示すことができる。
本明細書において、
「ハロゲン」は、フルオロ、クロロ、ブロム又はヨードを示し、好ましくはフルオロ、クロロ、ブロモを示す。
【００２１】
「アルキル」は、直鎖状又は分岐鎖状であることができ、例えば、Ｃ１−４アルキルを示すことができ、具体的には、メチル、エチル、ｎ−もしくはｉｓｏ−プロピル、ｎ−、ｉｓｏ−、ｓｅｃ−もしくはｔｅｒｔ−ブチル等を例示することができる。
【００２２】
「アルコキシ」は、アルキル部分が上記の意味を有するアルキル−Ｏ−基を示し、例えば、Ｃ１−４アルコキシであることができ、具体的には、メトキシ、エトキシ、ｎ−もしくはｉｓｏ−プロポキシ、ｎ−、ｉｓｏ−、ｓｅｃ−もしくはｔｅｒｔ−ブトキシ等が挙げられる。
【００２３】
「ハロアルキル」は、少なくとも１つの水素がハロゲンで置換された直鎖状又は分岐鎖状のアルキルを示し、例えば、１〜６個のフルオロ、クロロ及び／又はブロムにより置換されたＣ１−４アルキルを例示することができ、その具体例としては、フルオロメチル、クロロメチル、ジクロロメチル、ブロモメチル、ジフルオロメチル、トリフルオロメチル、クロロジフルオロメチル、ジクロロメチル、トリクロロメチル、２，２，２−トリフルオロエチル、２−クロロ−１，１，２−トリフルオロエチル、３−フルオロプロピル、３−クロロプロピル、２，２，３，３，３−ペンタフルオロプロピル、１，２，２，３，３，３−ヘキサフルオロプロピル等を挙げることができる。
【００２４】
「ハロアルコキシ」及び「ハロアルキルチオ」におけるハロアルキル部分は、前記「ハロアルキル」と同義であることができ、具体的に「ハロアルコキシ」としては、例えば、ジフルオロメトキシ、トリフルオロメトキシ、クロロジフルオロメトキシ、ジクロロメトキシ、２−フルオロエトキシ、２−クロロエトキシ、２，２，２−トリフルオロエトキシ、３−クロロプロポキシ等が挙げられ、また、「ハロアルキルチオ」としては、例えば、ジフルオロメチルチオ、トリフルオロメチルチオ、２，２，２−トリフルオロエチルチオ、３−フルオロプロピルチオ等を挙げることができる。
【００２５】
「ハロアルキレンジオキシ」は、直鎖状又は分岐鎖状であることができ、例えば、ジフルオロメチレンジオキシ、テトラフルオロエチレンジオキシ、１−メチル−２，２−ジフルオロエチレンジオキシ、１，１−ジメチル−２，２−ジフルオロエチレンジオキシ等を例示することができる。
【００２６】
「アルキリデン」は、直鎖状又は分岐鎖状であることができ、例えば、メチレン、エチリデン、ｎ−もしくはｉｓｏ−プロピリデン等が挙げられる。
【００２７】
本発明の好適な群の化合物としては、前記式（Ｉ）において、
Ｒ１がフルオロ、クロロ、ブロム、Ｃ１−４アルキル、Ｃ１−４アルコキシ、Ｃ１−４ハロアルキル、Ｃ１−４ハロアルコキシ、Ｃ１−４ハロアルキルチオ又はＣ１−４ハロアルキレンジオキシを示し、
ｍが１、２又は３を示し、
Ｒ２はメチルを示し、
Ｘがメチレン、酸素原子又は硫黄原子を示し、そして
Ａが基
【００２８】
【化９】
を示し、ここで
ＱがＣ１−４アルキルを示し、
Ｑ−ｈａｌがＣ１−４ハロアルキルを示し、そして
Ｈａｌがクロロ又はブロモを示す、
化合物が挙げられる。
【００３０】
本発明の更に好ましい群の化合物としては、前記式（Ｉ）において、
Ｒ１がフルオロ、クロロ、ブロム、メチル、メトキシ、トリフルオロメチル、クロロジフルオロメチル、トリクロロメチル、ジフルオロメトキシ、クロロジフルオロメトキシ、トリフルオロメトキシ、トリフルオロエトキシ、ジクロロメトキシ、ジフルオロメチルチオ、トリフルオロメチルチオ、ジフルオロメチレンジオキシ又はテトラフルオロエチレンジオキシを示し、
ｍが１、２又は３を示し、
ｍが１を示すとき、Ｒ１はフェニル基の３位に結合し、
ｍが２を示すとき、２個のＲ１はフェニル基の３位及び４位に結合するか又は３位及び５位に結合し、且つ２個のＲ１は同一もしくは相異なり、
ｍが３を示すとき、３個のＲ１はフェニル基の３位、４位及び５位に結合し、且つ３個のＲ１は同一もしくは相異なり、
Ｒ２がメチルを示し、
Ｘがメチレン、酸素原子又は硫黄原子を示し、そして
Ａが基
【００３１】
【化１０】
を示し、ここで
Ｑがメチル又はｔｅｒｔ−ブチルを示し、
Ｑ−ｈａｌがフルオロメチル、クロロメチル、ジクロロメチル又はブロモメチルを示し、そして
Ｈａｌがクロロ又はブロモを示す、
化合物が挙げられる。
【００３３】
前記製法（ａ）は、原料として、例えば、５−Ｎ−メチルアミノ−３−（３−トリフルオロメチルフェニル）−４−チアゾリジノンおよび２，２−ビス（クロロメチル）プロパノイルクロリドを用いる場合、下記反応式で表される。
【００３４】
【化１１】
前記製法（ａ）において原料として用いられる式（ＩＩ）の化合物は、その一部は従来の文献に未記載の新規化合物であり、例えば、前記特許文献１、特許文献３等記載の方法により容易に製造することができる。
【００３６】
式（ＩＩ）の化合物の代表例としては、下記のものを例示することができる。
【００３７】
５−Ｎ−メチルアミノ−３−（３−トリフルオロメチルフェニル）−４−チアゾリジノン、
５−Ｎ−メチルアミノ−３−（３−トリフルオロメトキシフェニル）−４−チアゾリジノン、
５−Ｎ−メチルアミノ−３−（３−クロロ−４−フルオロフェニル）−４−チアゾリジノン、
５−Ｎ−メチルアミノ−３−（３−ブロモ−４−フルオロフェニル）−４−チアゾリジノン、
５−Ｎ−メチルアミノ−３−（４−フルオロ−３−トリフルオロメチルフェニル）−４−チアゾリジノン、
５−Ｎ−メチルアミノ−３−（４−クロロ−３−トリフルオロメチルフェニル）−４−チアゾリジノン、
５−Ｎ−メチルアミノ−３−（３−トリフルオロメチルチオフェニル）−４−チアゾリジノン、
３−Ｎ−メチルアミノ−１−（３−トリフルオロメチルフェニル）−２−ピロリジノン、
３−Ｎ−メチルアミノ−１−［３，４−ビス（トリフルオロメチル）フェニル］−２−ピロリジノン、
３−Ｎ−メチルアミノ−１−（３−トリフルオロメトキシフェニル）−２−ピロリジノン、
３−Ｎ−メチルアミノ−１−（３−ジフルオロメトキシフェニル）−２−ピロリジノン、
３−Ｎ−メチルアミノ−１−（３−クロロ−４−フルオロフェニル）−２−ピロリジノン、
３−Ｎ−メチルアミノ−１−（４−クロロ−３−トリフルオロメチルフェニル）−２−ピロリジノン、
３−Ｎ−メチルアミノ−１−（３−メトキシ−４−メチルフェニル）−２−ピロリジノン、
５−Ｎ−メチルアミノ−３−（３−トリフルオロメチルフェニル）−４−オキサゾリジノン、
５−Ｎ−メチルアミノ−３−（３−トリフルオロメトキシフェニル）−４−オキサゾリジノン、
５−Ｎ−メチルアミノ−３−（３−ジフルオロメトキシフェニル）−４−オキサゾリジノン、
５−Ｎ−メチルアミノ−３−（３−クロロ−４−フルオロフェニル）−４−オキサゾリジノン、
５−Ｎ−メチルアミノ−３−（３，５−ジクロロ−４−フルオロフェニル）−４−オキサゾリジノン、
５−Ｎ−メチルアミノ−３−（４−クロロ−３−トリフルオロメチルフェニル）−４−オキサゾリジノン等。
【００３８】
上記製法（ａ）において原料として用いられる式（ＩＩＩ）の化合物は、一部新規化合物を包含し、例えば、式（ＩＩＩ）においてＭがハロゲンを示す酸ハライド類は、同じくＭが水酸基を示す相当するカルボン酸類をハロゲン化剤、例えば、オキシ塩化リン、オキシ臭化リン、三塩化リン、三臭化リン、ホスゲン類、二塩化オキサリル、塩化チオニル、臭化チオニル等と反応させることにより製造することができる。また、いくつかのハロゲン置換された酸ハライド類は、例えば、ドイツ特許公開第３１１１８４８号明細書、ドイツ特許公開第３３２６８７５号明細書等に記載の既知化合物である。
【００３９】
式（ＩＩＩ）の化合物の代表例としては、下記のものを例示することができる。
【００４０】
３−クロロ−２，２−ジメチルプロパノイルクロリド、
２，２−ビス（クロロメチル）プロパノイルクロリド、
３，３−ジクロロ−２，２−ジメチルプロパノイルクロリド、
３−フルオロ−２，２−ジメチルプロパノイルクロリド、
２，２−ビス（フルオロメチル）プロパノイルクロリド、
３−クロロ−２，２−ジメチルプロピオン酸、
２，２−ビス（クロロメチル）プロピオン酸、
３，３−ジクロロ−２，２−ジメチルプロピオン酸、
３−フルオロ−２，２−ジメチルプロピオン酸、
２，２−ビス（フルオロメチル）プロピオン酸等。
【００４１】
式（ＩＩＩ）においてＭが水酸基を示すカルボン酸類は、有機化学分野でよく知られた化合物を包含し、例えば、エステル類の加水分解、アルコール類、アルデヒド類、ケトン類の酸化等の方法により容易に製造することができる。
【００４２】
上記製法（ａ）の反応は適当な希釈剤中で実施することができ、その際に使用される希釈剤としては、例えば、脂肪族、環脂肪族及び芳香族炭化水素類（場合によっては塩素化されてもよい）、例えば、ペンタン、ヘキサン、シクロヘキサン、石油エーテル、リグロイン、ベンゼン、トルエン、キシレン、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロルベンゼン、ジクロロベンゼン等；エーテル類、例えば、エチルエーテル、メチルエチルエーテル、イソプロピルエーテル、ブチルエーテル、ジオキサン、ジメトキシエタン（ＤＭＥ）、テトラヒドロフラン（ＴＨＦ）、ジエチレングリコールジメチルエーテル（ＤＧＭ）等；ケトン類、例えば、アセトン、メチルエチルケトン（ＭＥＫ）、メチル−イソプロピルケトン、メチルイソブチルケトン（ＭＩＢＫ）等；ニトリル類、例えば、アセトニトリル、プロピオニトリル等；エステル類、例えば、酢酸エチル、酢酸アミル等；酸アミド類、例えば、ジメチルホルムアミド（ＤＭＦ）、ジメチルアセトアミド（ＤＭＡ）、Ｎ−メチルピロリドン等；スルホン、スルホキシド類、例えば、ジメチルスルホキシド（ＤＭＳＯ）、スルホラン等；塩基、例えば、ピリジン等を挙げることができる。
【００４３】
製法（ａ）は、酸結合剤又は縮合剤の存在下で行うことができ、使用しうる酸結合剤としては、無機塩基として、アルカリ金属の水素化物及び炭酸塩等、例えば、水素化ナトリウム、水素化リチウム、炭酸ナトリウム、炭酸カリウム等；そして有機塩基として、第３級アミン類、ジアルキルアミノアニリン類及びピリジン類、例えば、トリエチルアミン、１，１，４，４−テトラメチルエチレンジアミン（ＴＭＥＤＡ）、ピリジン、４−ジメチルアミノピリジン（ＤＭＡＰ）、１，４−ジアザビシクロ［２，２，２］オクタン（ＤＡＢＣＯ）、１，８−ジアザビシクロ［５，４，０］ウンデク−７−エン（ＤＢＵ）等を挙げることができ、また、縮合剤としては、カルボジイミド類；例えば、Ｎ，Ｎ′−ジシクロヘキシルカルボジイミド、Ｎ−（３−ジメチルアミノプロピル）−Ｎ′−エチルカルボジイミド塩酸塩等を挙げることができる。
【００４４】
製法（ａ）の反応は実質的に広い温度範囲内において実施することができるが、一般には約−２０〜約１４０℃、好ましくは約０〜約１００℃の間の温度が好適である。また、該反応は常圧下で行うことが望ましいが、場合により加圧下または減圧下で操作することもできる。
【００４５】
また、式（ＩＩＩ）において、Ｍが水酸基を示す場合、該製法は場合により添加剤を加えて行うこともでき、使用しうる添加剤としては、例えば、Ｎ−ヒドロキシベンゾトリアゾール、Ｎ−ヒドロキシスクシンイミド、３，４−ジヒドロ−３−ヒドロキシ−４−オキソ−１，２，３−ベンゾトリアジン等を挙げることができる。
【００４６】
製法（ａ）を実施するにあたって、例えば、希釈剤例えばテトラヒドロフラン中で、式（ＩＩ）の化合物１モルに対し１〜５モルの（ＩＩＩ）の化合物を、１〜５モルのトリエチルアミン存在下で反応させることにより、目的とする式（Ｉ）の化合物を得ることができる。
【００４７】
本発明の前記式（Ｉ）の活性化合物は、後記生物試験例に示す如く、各種雑草に対して優れた除草活性を示し、除草剤として使用することができる。本明細書において、「雑草」とは広義に望ましくない場所に生育するすべての植物を意味する。本発明の化合物は、使用濃度に依存して非選択性または選択性除草剤として作用する。本発明の活性化合物は、例えば、下記の雑草と栽培植物との間で使用することができる。
【００４８】
また、本発明の式（Ｉ）の活性化合物は、前述のとおり、他の除草活性化合物又は薬害軽減剤と混合することにより、混合除草剤組成物として、より一層強力な除草効果ならびに選択性を示すことができる。
【００４９】
次の属に属する双子葉雑草：カラシ（Ｓｉｎａｐｉｓ）、マメグンバイナズナ（Ｌｅｉｐｉｄｉｕｍ）、ヤエムグラキヌタソウ（Ｇａｌｉｕｍ）、ハコベ（Ｓｔｅｌｌａｒｉａ）、アカザ・アリタソウ（Ｃｈｅｎｏｐｏｄｉｕｍ）、イラクサ（Ｕｒｔｉｃａ）、ハンゴウソウ・ノボロギク・キオン（Ｓｅｎｅｃｉｏ）、ヒユ・ハゲイトウ（Ａｍａｒａｎｔｈｕｓ）、スベリヒユ・マツバボタン（Ｐｏｒｔｕｌａｃａ）、オナモミ（Ｘａｎｔｈｉｕｍ）、アサガオ（Ｉｐｏｍｏｅａ）、ミチヤナギ（Ｐｏｌｙｇｏｎｕｍ）、ブタクサ（Ａｍｂｒｏｓｉａ）、ノアザミ・フジアザミ（Ｃｉｒｓｉｕｍ）、ノゲシ（Ｓｏｎｃｈｕｓ）、ナス・ジャガイモ（Ｓｏｌａｎｕｍ）、イヌガラシ（Ｒｏｒｉｐｐａ）、オドリコソウ（Ｌａｍｉｕｍ）、クワガタソウ・イヌノフグリ（Ｖｅｒｏｎｉｃａ）、チョウセンアサガオ（Ｄａｔｕｒａ）、スミレパンジー（Ｖｉｏｌａ）、チシマオドロ（Ｇａｌｅｏｐｓｉｓ）、ケシ（Ｐａｐａｖｅｒ）、ヤグルマギク（Ｃｅｎｔａｕｒｅａ）、ハキダメギク（Ｇａｌｉｎｓｏｇａ）、キカシグサ（Ｒｏｔａｌａ）、アゼナ（Ｌｉｎｄｅｒｎｉａ）等。 次の属に属する双子葉栽培植物：ワタ（Ｇｏｓｓｙｐｉｕｍ）、ダイズ（Ｇｌｙｃｉｎｅ）、フダンソウ・サトウダイコン（Ｂｅｔａ）、ニンジン（Ｄａｕｃｕｓ）、インゲンマメ・アオイマダ（Ｐｈａｓｅｏｌｕｓ）、エンドウ（Ｐｉｓｕｍ）、ナス・ジャガイモ（Ｓｏｌａｎｕｍ）、アマ（Ｌｉｎｕｍ）、サツマイモ・アサガオ（Ｉｐｏｍｏｅａ）、ソラマメ・ナンテンハギ（Ｖｉｃｉａ）、タバコ（Ｎｉｃｏｔｉａｎａ）、トマト（Ｌｙｃｏｐｅｒｓｉｃｏｎ）、ナンキンマメ（Ａｒａｃｈｉｓ）、アブラナ・ハクサイ・カブラ・キャベツ（Ｂｒａｓｓｉｃａ）、アキノノゲシ（Ｌａｃｔｕｃａ）、キュウリ・メロン（Ｃｕｃｕｍｉｓ）カボチャ（Ｃｕｃｕｒｂｉｔａ）等。
【００５０】
次の属に属する単子葉雑草：ヒエ（Ｅｃｈｉｎｏｃｈｌｏａ）、エノコロ・アワ（Ｓｅｔａｒｉａ）、キビ（Ｐａｎｉｃｕｍ）、メヒシバ（Ｄｉｇｉｔａｒｉａ）、アワガリエ・チモシー（Ｐｈｌｅｕｍ）、イチゴツナギ・スズメノカタビラ（Ｐｏａ）、ウシノケグサ・トボシガラ（Ｆｅｓｔｕｃａ）、オヒシバ・シコクビエ（Ｅｌｅｕｓｉｎｅ）、ドクムギ（Ｌｏｌｉｕｍ）、キツネガヤ・イヌムギ（Ｂｒｏｍｕｓ）、カラスムギ・オートムギ（エンバク）（Ａｖｅｎａ）、カヤツリグサ・パピルス・シチトウイ・ハマスゲ（Ｃｙｐｅｒｕｓ）、モロコシ（Ｓｏｒｇｈｕｍ）、カモジグサ（Ａｇｒｏｐｙｒｏｎ）、コナギ（Ｍｏｎｏｃｈｏｒｉａ）、テンツキ（Ｆｉｍｂｒｉｓｔｙｌｉｓ）、オモダカ・クワイ（Ｓａｇｉｔｔａｒｉａ）、ハリイ・クログワイ（Ｅｌｅｏｃｈａｒｉｓ）、ホタルイ・ウキヤグラ・フトイ（Ｓｃｉｒｐｕｓ）、スズメノヒエ（Ｐａｓｐａｌｕｍ）、カモノハシ（Ｉｓｃｈａｅｍｕｍ）、ヌカボ（Ａｇｒｏｓｔｉｓ）、スズメノテッポウ（Ａｌｏｐｅｃｕｒｕｓ）ギヨウギシバ（Ｃｙｎｏｄｏｎ）等。
【００５１】
次の属に属する単子葉栽培植物：イネ（Ｏｒｙｚａ）、トウモロコシ・ホップコーン（Ｚｅａ）、コムギ（Ｔｒｉｔｉｃｕｍ）、オオムギ（Ｈｏｒｄｅｕｍ）、カラスムギ・オートムギ（エンバク）（Ａｖｅｎａ）、ライムギ（Ｓｅｃａｌｅ）、モロコシ（Ｓｏｒｇｈｕｍ）、キビ（Ｐａｎｉｃｕｍ）、サトウキビ・ワセオバナ（Ｓａｃｃｈａｒｕｍ）、パイナップル（Ａｎａｎａｓ）、アスパラガス（Ａｓｐａｒａｇｕｓ）、ネギ・ニラ（Ａｌｌｉｕｍ）等。
【００５２】
本発明の前記式（Ｉ）の活性化合物及び混合除草剤組成物は、特に、水田雑草に対して使用することができる。本発明の化合物及び混合除草剤組成物を用いて防除することができる水田雑草としては、具体的には、例えば、キカシグサ（Ｒｏｔａｌａ ｉｎｄｉｃａ Ｋｏｅｈｎｅ）、アゼナ（Ｌｉｎｄｅｒｎｉａ Ｐｒｏｃｕｍｂｅｎｓ Ｐｈｉｌｃｏｘ）、チヨウジタデ（Ｌｕｄｗｉｇｉａ ｐｒｏｓｔｒａｔａ Ｒｏｘｂｕｒｇｈ）、ヒルムシロ（Ｐｏｔａｍｏｇｅｔｏｎ ｄｉｓｔｉｎｃｔｕｓ Ａ．Ｂｅｎｎ）、ミゾハコベ（Ｅｌａｔｉｎｅ ｔｒｉａｎｄｒａ Ｓｃｈｋ）、セリ（Ｏｅｎａｎｔｈｅ ｊａｖａｎｉｃａ）、タイヌビエ（Ｅｃｈｉｎｏｃｈｌｏａ ｏｒｙｚｉｃｏｌａ Ｖａｓｉｎｇ）、コナギ（Ｍｏｎｏｃｈｏｒｉａ ｖａｇｉｎａｌｉｓ Ｐｒｅｓｌ）、マツバイ（Ｅｌｅｏｃｈａｒｉｓ ａｃｉｃｕｌａｒｉｓ Ｌ．）、クログワイ（Ｅｌｅｏｃｈａｒｉｓ Ｋｕｒｏｇｕｗａｉ Ｏｈｗｉ）、タマガヤツリ（Ｃｙｐｅｒｕｓ ｄｉｆｆｏｒｍｉｓ Ｌ．）、ミズガヤツリ（Ｃｙｐｅｒｕｓ ｓｅｒｏｔｉｎｕｓ Ｒｏｔｔｂｏｅｌ）、ウリカワ（Ｓａｇｉｔｔａｒｉａ ｐｙｇｍａｅａ Ｍｉｑ）、ヘラオモダカ（Ａｌｉｓｍａ ｃａｎａｌｉｃｕｌａｔｕｍ Ａ． Ｂｒ． ｅｔ Ｂｏｕｃｈｅ）、ホタルイ（Ｓｃｉｒｐｕｓ ｊｕｎｃｏｉｄｅｓ Ｒｏｘｂｕｒｇｈ）等を挙げることができる。また、本発明の前記式（Ｉ）の活性化合物及び混合除草剤組成物は、スルホニルウレア系除草剤に対し耐性を示す雑草に対して使用することができる。該耐性雑草としては、具体的には、例えば、キカシグサ（Ｒｏｔａｌａ ｉｎｄｉｃａ Ｋｏｅｈｎｅ）、アゼナ（Ｌｉｎｄｅｒｎｉａ Ｐｒｏｃｕｍｂｅｎｓ Ｐｈｉｌｃｏｘ）、アメリカアゼナ（Ｌｉｎｄｅｒｎｉａ ｄｕｂｉａ Ｌ． ＰＥＮＮＥＬ）、タケトアゼナ（Ｌｉｎｄｅｒｎｉａ ｖａｒ． ｄｕｂｉａ Ｐｅｎｎｅｌｌ）、アゼトウガラシ（Ｌｉｎｄｅｒｎｉａ ａｎｇｕｓｔｉｆｏｌｉａ Ｗｅｔｔｓｔｅｉｎ）、ミゾハコベ（Ｅｌａｔｉｎｅ ｔｒｉａｎｄｒａ Ｓｃｈｋ）、ミズアオイ（Ｍｏｎｏｃｈｏｒｉａ ｋｏｒｓａｋｏｗｉｉ ＲＥＧＥＬ ＆ ＭＡＡＣＫ）、コナギ（Ｍｏｎｏｃｈｏｒｉａ ｖａｇｉｎａｌｉｓ Ｐｒｅｓｌ）、ホタルイ（Ｓｃｉｒｐｕｓ ｊｕｎｃｏｉｄｅｓ Ｒｏｘｂｕｒｇｈ）等を挙げることができる。しかしながら、本発明の前記式（Ｉ）の活性化合物及び混合除草剤組成物の使用は、これらの雑草に対する使用に限定されるものではなく、他の水田雑草及びスルホニルウレア系除草剤耐性雑草以外の雑草に対しても同様に適用することができる。
【００５３】
本発明の化合物の使用は、上記の植物に限定されるものではなく、他の植物に対しても同様に適用され得る。また、使用濃度によって、本発明の活性化合物は、雑草を非選択的に防除することができ、例えば、工場等の産業用地、鉄道軌道、道路、植林地、非植林地等において使用することができる。更に、本発明の活性化合物は、多年性植物栽培において、雑草防除のために使用することができ、例えば、植林、観賞用植林、果樹園、ブドウ園、カンキツ果樹園、ナッツ果樹園、バナナ栽培場、コーヒー栽培場、茶栽培場、ゴム栽培場、ギネアアブラヤシ栽培場、ココア栽培場、小果樹園、ホップ栽培地等に適用することができ、また、一年性植物栽培において、選択的雑草防除のために適用することもできる。
【００５４】
本発明の活性化合物及び混合除草剤組成物は、実際に使用するにあたり、通常の製剤形態にすることができる。その製剤形態としては、例えば、液剤、水和剤、エマルジョン、懸濁剤、粉剤、顆粒性水和剤、錠剤、粒剤、懸濁エマルジョン濃厚物、重合体物質中のマイクロカプセル、ジャンボ剤等を挙げることができる。
【００５５】
これらの製剤は、それ自体既知の方法で製造することができ、例えば、活性化合物を、展開剤、即ち、液体又は固体の希釈剤又は担体、及び場合によっては界面活性剤、即ち、乳化剤及び／又は分散剤及び／又は泡沫形成剤と混合することによって調製することができる。
【００５６】
液体の希釈剤又は担体としては、例えば、芳香族炭化水素（例えば、キシレン、トルエン、アルキルナフタレン等）、クロル化芳香族又はクロル化脂肪族炭化水素（例えば、クロロベンゼン類、塩化エチレン類、塩化メチレン等）、脂肪族炭化水素［例えば、シクロヘキサン等、パラフィン類（例えば、鉱油留分等）］、アルコール類（例えば、ブタノール、グリコール等）及びそれらのエーテル、エステル等、ケトン類（例えば、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等）、強極性溶媒（例えば、ジメチルホルムアミド、ジメチルスルホキシド等）、水等を挙げることができる。展開剤として水を用いる場合には、例えば、有機溶媒を補助溶媒として使用することができる。
【００５７】
固体の希釈剤又は担体としては、例えば、粉砕天然鉱物（例えば、カオリン、クレー、タルク、チョーク、石英、アタパルガイド、モンモリロナイト、珪藻土等）、粉砕合成鉱物（例えば、高分散ケイ酸、アルミナ、ケイ酸塩等）等を挙げることができる。粒剤のための固体担体としては、粉砕且つ分別された岩石（例えば、方解石、大理石、軽石、海泡石、白雲石等）、無機及び有機物粉の合成粒、有機物質（例えば、おがくず、ココやしの実のから、とうもろこしの穂軸、タバコの茎等）の細粒体等を挙げることができる。
【００５８】
乳化剤及び／又は泡沫剤としては、例えば、非イオン及び陰イオン乳化剤［例えば、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレン脂肪酸アルコールエーテル（例えば、アルキルアリールポリグリコールエーテル、アルキルスルホン酸塩、アルキル硫酸塩、アリールスルホン酸塩等）］、アルブミン加水分解生成物等を挙げることができる。
【００５９】
分散剤には、例えば、リグニンサルファイト廃液やメチルセルロース等が包含される。
【００６０】
固着剤も製剤（粉剤、粒剤、乳剤）に使用することができ、該固着剤としては、例えば、カルボキシメチルセルロース、天然及び合成ポリマー（例えば、アラビアゴム、ポリビニルアルコール、ポリビニルアセテート等）を挙げることができる。
【００６１】
着色剤を使用することもでき、該着色剤としては、無機顔料（例えば、酸化鉄、酸化チタン、プルシアンブルー等）、アリザリン染料、アゾ染料又は金属フタロシアニン染料のような有機染料、更に、鉄、マンガン、ボロン、銅、コバルト、モリブデン、亜鉛等の金属の塩のような微量要素を挙げることができる。
【００６２】
該製剤は、一般に、式（Ｉ）の活性化合物を０．１〜９５重量％、好ましくは０．５〜９０重量％の範囲内で含有することができる。
【００６３】
本発明の式（Ｉ）の活性化合物は、それ自体で又はそれらの製剤形態で、雑草防除のために使用することができ、また、公知の除草剤との混合除草剤組成物は、予め最終的製剤形態に調製されていてもよく、又は使用時にタンクミックスすることによって調製することもできる。混合除草剤組成物として本発明の式（Ｉ）の化合物と組み合わせて使用しうる除草剤としては、例えば、一般名で表される下記の除草剤を具体例として例示することができる。
【００６４】
アセトアミド系除草剤：例えば、プレチラクロール、ブタクロール、テニルクロール、アラクロール等；
アミド系除草剤：例えば、クロメプロップ、エトベンザニド等；
ベンゾフラン系除草剤：例えば、ベンフレセート等；
インダンジオン系除草剤：例えば、インダノファン等；
ピラゾール系除草剤：例えば、ピラゾレート、ベンゾフェナップ、ピラゾキシフェン等；
オキサジノン系除草剤：例えば、オキサジクロメホン等；
スルホニルウレア系除草剤：例えば、ベンスルフロン・メチル、アジムスルフロン、イマゾスルフロン、ピラゾスルフロン・エチル、シクロスルファムロン、エトキシスルフロン、ハロスルフロン・メチル等；
チオカーバメート系除草剤：例えば、チオベンカルブ、モリネート、ピリブチカルブ等；
トリアジン系除草剤：例えば、ジメタメトリン、シメトリン等；
トリアゾール系除草剤：例えば、カフェンストロール等；
キノリン系除草剤：例えば、キンクロラック等；
イソキサゾール系除草剤：例えば、イソキサフルトール等；
ジチオホスフェート系除草剤：例えば、アニロホス等；
オキシアセトアミド系除草剤：例えば、メフェナセット、フルフェナセット等；
テトラゾリノン系除草剤：例えば、フェントラザミド等；
ジカルボキシイミド系除草剤：例えば、ペントキサゾン等；
トリオン系除草剤：例えば、スルコトリオン、ベンゾビシクロン等；
フェノキシプロピネート系除草剤：例えば、シハロホップ・ブチル等；
ベンゾイックアッシド系除草剤：例えば、ピリミノバック・メチル等；
ジフェニルエーテル系除草剤：例えば、クロメトキシフェン、オキシフルオルフェン等；
ピリジンジカルボチオエート系除草剤：例えば、ジチオピル等；
フェノキシ系除草剤：例えば、ＭＣＰＡ、ＭＣＰＢ等；
ウレア系除草剤：例えば、ダイムロン、クミルロン等；
ナフタレンジオン系除草剤：例えば、キノクラミン等；
イソキサゾリジノン系除草剤：例えば、クロマゾン等。
【００６５】
上記の活性化合物は、“Ｐｅｓｔｉｃｉｄｅ Ｍａｎｕａｌ”， ２０００年， Ｂｒｉｔｉｓｈ Ｃｒｏｐ Ｐｒｏｔｅｃｔ Ｃｏｕｎｃｉｌ 発行に記載された公知の除草剤である。
【００６６】
また、本発明の式（Ｉ）の活性化合物は、薬害軽減剤と混合すると、この混合により、薬害が軽減され、より広い雑草防除のスペクトルが提供され、選択性除草剤としての適用をより広くすることができる。
【００６７】
該薬害軽減剤としては、例えば、一般名又は開発コードで表される次の化合物を挙げることができる。
【００６８】
ＡＤ−６７、ＢＡＳ−１４５１３８、ベノキサコル、クロキントセットメキシル、シオメトリニル、２，４−Ｄ、ＤＫＡ−２４、ジクロルミッド、ダイムロン、フェンクロリム、フェンクロラゾールエチル、フルラゾール、フルキソフェニム、フリラゾール、イソキサジフェンエチル、メフェンピルジエチル、ＭＧ−１９１、ナフタリックアンハイドライド、オキサベトリニル、ＰＰＧ−１２９２、Ｒ−２９１４８等。
【００６９】
上記の薬害軽減剤もまた、“Ｐｅｓｔｉｃｉｄｅ Ｍａｎｕａｌ”，２０００年， Ｂｒｉｔｉｓｈ Ｃｒｏｐ Ｐｒｏｔｅｃｔ Ｃｏｕｎｃｉｌ 発行に記載されている。
【００７０】
更に、本発明の式（Ｉ）の化合物と上記除草剤とからなる混合除草剤組成物には、さらに、上記薬害軽減剤を混合することも可能であり、この混合により、薬害が軽減され且つより広い雑草防除のスペクトルが提供され、選択性除草剤としての適用をより広くすることができる。
【００７１】
驚くべきことに、本発明の化合物と公知の除草剤及び／又は薬害軽減剤とのいくつかの混合除草剤組成物はまた、相乗効果を現すことができる。
【００７２】
本発明の式（Ｉ）の活性化合物を使用する場合、そのまま直接使用するか、又は散布用調製液、乳剤、錠剤、懸濁剤、粉剤、ペースト、粒剤のような製剤形態で使用するか、又は更に希釈して調製された使用形態で使用することができる。本発明の活性化合物は、例えば、液剤散布（ｗａｔｅｒｉｎｇ）、噴霧（ｓｐｒａｙｉｎｇ， ａｔｏｍｉｚｉｎｇ）、散粒等の方法で施用することができる。
【００７３】
本発明の式（Ｉ）の活性化合物は、植物の発芽前及び発芽後のいずれの段階でも使用することができる。また、それらは播種前に土壌中に取り込ませることもできる。
【００７４】
本発明の活性化合物の施用量は実質的範囲内でかえることができる。それは望むべき効果の性質に依存して基本的に異なる。除草剤として使用する場合、施用量としては、例えば、１ヘクタール当たり、活性化合物として約０．０１〜約４ｋｇ、好ましくは約０．０５〜約３ｋｇの範囲内を例示することができる。
【００７５】
次に、本発明の化合物の製造及び用途を下記の実施例によりさらに具体的に示すが、本発明はこれらのみに限定されるべきものではない。
【００７６】
【実施例】
化合物製造実施例
合成例１
【００７７】
【化１２】
２，２−ビス（クロロメチル）プロパノイルクロリド（０．３４ｇ）をＴＨＦ（５ｍｌ）に溶解させ、これを５−Ｎ−メチルアミノ−３−（３−トリフルオロメチルフェニル）−４−チアゾリジノン（０．５０ｇ）、トリエチルアミン（０．１８ｇ）のＴＨＦ（１０ｍｌ）溶液に室温で滴下しそのまま３時間撹拌した。反応後、冷水を加え、酢酸エチル（５０ｍｌ）で抽出し、ついで飽和食塩水にて洗浄し、無水硫酸マグネシウムで乾燥させた。酢酸エチルを留去して得られた残留物をシリカゲルカラムクロマトグラフィー（溶出溶媒；酢酸エチル；ヘキサン＝１：１）により精製し、目的の５−｛２，２−ビス（クロロメチル）プロパノイル−Ｎ−メチル｝アミノ−３−（３−トリフルオロメチルフェニル）−４−チアゾリジノン（０．６４ｇ）を得た。ｍｐ：１１５−１１６℃
上記合成例１に例示される本発明の式（Ｉ）の化合物の製法に準じて操作することにより得られる化合物を、合成例１で合成した化合物と共に、下記第１表に示す。
【００７９】
本発明の式（Ｉ）の化合物が式
【００８０】
【化１３】
を示す場合の化合物例を第１表に示す。
【００８２】
第１表において、Ｍｅはメチルを示し、ｔ−Ｂｕはｔｅｒｔ−ブチルを示す。
【００８３】
第１表
【００８４】
【表１】
【００８６】
【化１４】
ジクロロメタン（３０ｍｌ）に５−クロロ−３−（３−トリフルオロメチルフェニル）−４−チアゾリジノン（１１．０ｇ）を溶解させ、これを４０％メチルアミン水溶液（４５．５ｇ）、ヨウ化ナトリウム（０．５９ｇ）、トリエチルベンジルアンモニウムクロリド（０．８９ｇ）及びジクロロメタン（３０ｍｌ）の混合溶液に氷冷下で滴下し、そのまま１時間氷冷下で撹拌した。反応後、ジクロロメタン（５０ｍｌ）で抽出し、ついで飽和食塩水にて洗浄し、無水硫酸マグネシウムで乾燥させた。ジクロロメタンを留去して得られた残留物をシリカゲルカラムクロマトグラフィー（溶出溶媒；酢酸エチル：ヘキサン＝１：１から２：１）により精製し、５−Ｎ−メチルアミノ−３−（３−トリフルオロメチルフェニル）−４−チアゾリジノン（５．８０ｇ）を得た。ｍｐ：８８−８９℃
生物試験例
試験例１：水田雑草に対する除草効果試験
活性化合物の調合剤の調製：
担体：ジメチルホルムアミド（ＤＭＦ） ５重量部
乳化剤：ベンジルオキシポリグリコールエーテル １重量部
活性物質の調合剤は、１重量部の活性化合物と、上記分量の担体および乳化剤とを混合することにより、乳剤として得られる。その調合剤の所定薬量を水で希釈する。
試験方法：
温室内において、水田土壌を詰めた５００ｃｍ２ポットに、２．５葉期（草丈１５ｃｍ）の水稲苗（品種：日本晴）を１ポット当たり１株３本植えとした。次いで、ヒエ、タマガヤツリ、ホタルイ、コナギ、広葉雑草（アゼナ、キカシグサ、ミゾハコベ、ヒメミソハギ、アブノメ等）、ミズガヤツリ、ウリカワの各種子または塊茎を接種し、約２〜３ｃｍ湛水した。
【００８８】
水稲移植５日後、前記調製法に従って調製した各活性化合物の調合剤の所定希釈液で水面処理した。処理後、３ｃｍの湛水状態を保ち、散布３週間後に除草効果を調査した。なお、除草効果の評価は、完全枯死を１００％とし、０％を除草効果なしとして行った。
結果：
その結果、代表例として、化合物番号１１、４９、５１、５２、５４、５７、６１、１６８、１７１、１７６、２６９および２７７の化合物は、いずれも、薬量（有効成分量）０．１２５ｋｇ／ｈａで、水田雑草に対し十分な除草効果を示し、移植水稲に対し安全性を示した。
試験例２：畑地雑草に対する発芽前土壌処理試験
試験方法：
温室内において、畑土壌を詰めた１２０ｃｍ２ポットの表層に、ヒエ、エノコログサ、アオビユ及びイヌタデの各種子を播種覆土し、上記試験例１と同様にして調製した所定薬量の希釈液を各試験ポットの土壌表層に均一に散布した。散布４週間後に除草効果の程度を調査した。
結果：
その結果、代表例として、化合物番号１６８、１７１、１７６、２６１および２８１の化合物は、いずれも、薬量（有効成分量）０．０６ｋｇ／ｈａで、ヒエ、エノコログサ、アオビユ及びイヌタデに対して９０％以上の殺草活性を示した。
試験例３：畑地雑草に対する発芽後茎葉処理試験
試験方法：
温室内において、畑土壌を詰めた１２０ｃｍ２ポットに、ヒエ、エノコログサ、アオビユ及びイヌタデの種子を播き覆土した。播種覆土１０日後（雑草は平均２葉期）に、上記試験例１と同様にして調製した所定薬量の希釈液を各試験ポットの茎葉部に均一に散布した。散布３週間後に除草効果の程度を調査した。
結果：
その結果、代表例として、化合物番号４５、６１、２６５および２８１の化合物は、いずれも、薬量（有効成分量）０．５ｋｇ／ｈａで、ヒエ、エノコログサ、アオビユ及びイヌタデに対して９０％以上の殺草活性を示した。
【００８９】
製剤実施例
製剤例１（粒剤）
本発明化合物Ｎｏ．５２（１０部）、ベントナイト（モンモリロナイト）（３０部）、タルク（滑石）（５８部）及びリグニンスルホン酸塩（２部）の混合物に、水（２５部）を加え、良く捏化し、押し出し式造粒機により、１０〜４０メッシュの粒状として、４０〜５０℃で乾燥して粒剤とする。
【００９０】
製剤例２（粒剤）
０．２〜２ｍｍに粒度分布を有する粘土鉱物粒（９５部）を回転混合機に入れ、回転下、液体希釈剤とともに本発明化合物Ｎｏ．４９（５部）を噴霧し均等に湿らせた後、４０〜５０℃で乾燥し粒剤とする。
【００９１】
製剤例３（乳剤）
本発明化合物Ｎｏ．２６１（３０部）、キシレン（５部）、ポリオキシエチレンアルキルフェニルエーテル（８部）及びアルキルベンゼンスルホン酸カルシウム（７部）を混合撹拌して乳剤とする。
【００９２】
製剤例４（水和剤）
本発明化合物Ｎｏ．２８１（１５部）、ホワイトカーボン（含水無結晶酸化ケイ酸微粉末）と粉末クレーとの混合物（１：５）（８０部）、アルキルベンゼンスルホン酸ナトリウム（２部）及びアルキルナフタレンスルホン酸ナトリウムホルマリン重合物（３部）を粉末混合し、水和剤とする。
【００９３】
製剤例５（水和顆粒）
本発明化合物Ｎｏ．１７６（２０部）、リグニンスルホン酸ナトリウム（３０部）、ベントナイト（１５部）及び焼成ケイソウ土粉末（３５部）を十分に混合し、水を加え、０．３ｍｍのスクリーンで押し出し乾燥して、水和顆粒とする。
【００９４】
【発明の効果】
本発明の新規アゾリジン誘導体は、上記生物試験例から明らかなように、除草剤として優れた性質を有している。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel azolidine derivative and its use as a herbicide.
[0002]
[Prior art]
It has already been known that certain azolidine derivatives exhibit an action as a herbicide (see Patent Documents 1 to 3, Non-Patent Document 1, etc.).
[0003]
[Patent Document 1]
PCT International Application WO 95/33719 Pamphlet
[0004]
[Patent Document 2]
PCT International Application WO 97/20838 Pamphlet
[0005]
[Patent Document 3]
PCT International Application WO 00/21928 Pamphlet
[0006]
[Non-Patent Document 1]
American Chemical Society, 18-29 (2002)
[0007]
[Problems to be solved by the invention]
However, known derivatives disclosed in the above-mentioned publications as herbicides are not fully satisfactory in terms of herbicidal effects and / or safety.
[0008]
[Means for Solving the Problems]
As a result of intensive studies to create a novel useful compound having a higher effect as a herbicide and higher safety, the present inventors have represented the following formula having excellent biological activity. A novel azolidine derivative has been found.
[0009]
[Chemical formula 5]
Where
R1Represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkylthio or haloalkylenedioxy,
m represents 0, 1, 2, 3, 4 or 5;
2 to 5 R when m is 2, 3, 4 or 51Are the same or different,
R2Represents alkyl,
X represents an alkylidene, oxygen atom or sulfur atom, and
A is the group
[0011]
[Chemical 6]
Show here
Q represents alkyl,
Q-hal represents haloalkyl, and
Hal represents halogen.
[0013]
The compound of the said formula (I) of this invention is compoundable by the following manufacturing method (a), for example.
Manufacturing method (a):formula
[0014]
[Chemical 7]
Where R1, M, R2And X are as defined above,
A compound represented by the formula
[0016]
[Chemical 8]
In which M represents a halogen or a hydroxyl group; and
A is as defined above,
The method of making it react with the compound represented by these.
[0018]
The azolidine derivatives of formula (I) provided by the present invention exhibit a strong herbicidal activity. The azolidine derivative of the formula (I) according to the present invention is a novel compound that is conceptually included in the compound represented by the general formula (I) described in Patent Document 1, but is not specifically described in the pamphlet. is there. Surprisingly, it exhibits a very strong herbicidal action as compared with known compounds similar in structure specifically described in Patent Document 1.
[0019]
Therefore, it can be used as a herbicide of the azolidine derivative of formula (I) of the present invention.
[0020]
The azolidine derivative of the formula (I) according to the present invention, as will be specifically shown later, is mixed with other herbicidal active compounds or safeners to further enhance the herbicidal effect as a mixed herbicidal composition. As well as selectivity.
In this specification,
“Halogen” represents fluoro, chloro, bromo or iodo, preferably fluoro, chloro or bromo.
[0021]
“Alkyl” can be linear or branched, eg, C1-4Alkyl can be shown, and specific examples include methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
[0022]
“Alkoxy” refers to an alkyl-O— group in which the alkyl moiety has the meaning given above.1-4Specific examples include alkoxy, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy.
[0023]
“Haloalkyl” refers to a straight or branched alkyl in which at least one hydrogen is replaced by a halogen, for example, C substituted by 1 to 6 fluoro, chloro and / or bromine.1-4Alkyl can be exemplified, and specific examples thereof include fluoromethyl, chloromethyl, dichloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoro Ethyl, 2-chloro-1,1,2-trifluoroethyl, 3-fluoropropyl, 3-chloropropyl, 2,2,3,3,3-pentafluoropropyl, 1,2,2,3,3 3-hexafluoropropyl and the like can be mentioned.
[0024]
The haloalkyl moiety in “haloalkoxy” and “haloalkylthio” may have the same meaning as the above “haloalkyl”. Specifically, examples of the “haloalkoxy” include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, dichloro Examples thereof include methoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 3-chloropropoxy and the like, and examples of “haloalkylthio” include difluoromethylthio, trifluoromethylthio, 2 , 2,2-trifluoroethylthio, 3-fluoropropylthio and the like.
[0025]
“Haloalkylenedioxy” can be linear or branched, for example, difluoromethylenedioxy, tetrafluoroethylenedioxy, 1-methyl-2,2-difluoroethylenedioxy, 1,1 -Dimethyl-2,2-difluoroethylenedioxy and the like can be exemplified.
[0026]
“Alkylidene” may be linear or branched, and examples include methylene, ethylidene, n- or iso-propylidene, and the like.
[0027]
As a preferred group of compounds of the present invention, in the formula (I),
R1Is fluoro, chloro, bromo, C1-4Alkyl, C1-4Alkoxy, C1-4Haloalkyl, C1-4Haloalkoxy, C1-4Haloalkylthio or C1-4Haloalkylenedioxy,
m represents 1, 2 or 3,
R2Indicates methyl,
X represents a methylene, oxygen or sulfur atom, and
A based
[0028]
[Chemical 9]
Show here
Q is C1-4Indicates alkyl,
Q-hal is C1-4Represents haloalkyl, and
Hal represents chloro or bromo,
Compounds.
[0030]
As a further preferred group of compounds of the present invention, in the formula (I),
R1Is fluoro, chloro, bromo, methyl, methoxy, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, difluoromethoxy, chlorodifluoromethoxy, trifluoromethoxy, trifluoroethoxy, dichloromethoxy, difluoromethylthio, trifluoromethylthio, difluoromethylenedi Represents oxy or tetrafluoroethylenedioxy,
m represents 1, 2 or 3,
When m represents 1, R1Binds to the 3-position of the phenyl group,
When m represents 2, two R1Are bonded to the 3rd and 4th positions of the phenyl group, or bonded to the 3rd and 5th positions, and two R1Are the same or different,
When m represents 3, 3 R1Is bonded to the 3-position, 4-position and 5-position of the phenyl group, and 3 R1Are the same or different,
R2Indicates methyl,
X represents a methylene, oxygen or sulfur atom, and
A based
[0031]
[Chemical Formula 10]
Show here
Q represents methyl or tert-butyl;
Q-hal represents fluoromethyl, chloromethyl, dichloromethyl or bromomethyl, and
Hal represents chloro or bromo,
Compounds.
[0033]
In the production method (a), for example, when 5-N-methylamino-3- (3-trifluoromethylphenyl) -4-thiazolidinone and 2,2-bis (chloromethyl) propanoyl chloride are used as raw materials, It is represented by the following reaction formula.
[0034]
Embedded image
A part of the compound of the formula (II) used as a raw material in the production method (a) is a novel compound that has not been described in the conventional literature. For example, it can be easily obtained by the methods described in Patent Document 1, Patent Document 3, etc. Can be manufactured.
[0036]
The following can be illustrated as a typical example of the compound of Formula (II).
[0037]
5-N-methylamino-3- (3-trifluoromethylphenyl) -4-thiazolidinone,
5-N-methylamino-3- (3-trifluoromethoxyphenyl) -4-thiazolidinone,
5-N-methylamino-3- (3-chloro-4-fluorophenyl) -4-thiazolidinone,
5-N-methylamino-3- (3-bromo-4-fluorophenyl) -4-thiazolidinone,
5-N-methylamino-3- (4-fluoro-3-trifluoromethylphenyl) -4-thiazolidinone,
5-N-methylamino-3- (4-chloro-3-trifluoromethylphenyl) -4-thiazolidinone,
5-N-methylamino-3- (3-trifluoromethylthiophenyl) -4-thiazolidinone,
3-N-methylamino-1- (3-trifluoromethylphenyl) -2-pyrrolidinone,
3-N-methylamino-1- [3,4-bis (trifluoromethyl) phenyl] -2-pyrrolidinone,
3-N-methylamino-1- (3-trifluoromethoxyphenyl) -2-pyrrolidinone,
3-N-methylamino-1- (3-difluoromethoxyphenyl) -2-pyrrolidinone,
3-N-methylamino-1- (3-chloro-4-fluorophenyl) -2-pyrrolidinone,
3-N-methylamino-1- (4-chloro-3-trifluoromethylphenyl) -2-pyrrolidinone,
3-N-methylamino-1- (3-methoxy-4-methylphenyl) -2-pyrrolidinone,
5-N-methylamino-3- (3-trifluoromethylphenyl) -4-oxazolidinone,
5-N-methylamino-3- (3-trifluoromethoxyphenyl) -4-oxazolidinone,
5-N-methylamino-3- (3-difluoromethoxyphenyl) -4-oxazolidinone,
5-N-methylamino-3- (3-chloro-4-fluorophenyl) -4-oxazolidinone,
5-N-methylamino-3- (3,5-dichloro-4-fluorophenyl) -4-oxazolidinone,
5-N-methylamino-3- (4-chloro-3-trifluoromethylphenyl) -4-oxazolidinone and the like.
[0038]
The compound of the formula (III) used as a raw material in the above production method (a) partially includes a novel compound. For example, in the formula (III), acid halides in which M is halogen are equivalent to those in which M is a hydroxyl group. By reacting carboxylic acids with halogenating agents such as phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, phosphorus tribromide, phosgene, oxalyl dichloride, thionyl chloride, thionyl bromide, etc. Can do. Some halogen-substituted acid halides are known compounds described in, for example, German Patent Publication No. 311848, German Patent Publication No. 3326875, and the like.
[0039]
Typical examples of the compound of formula (III) include the following.
[0040]
3-chloro-2,2-dimethylpropanoyl chloride,
2,2-bis (chloromethyl) propanoyl chloride,
3,3-dichloro-2,2-dimethylpropanoyl chloride,
3-fluoro-2,2-dimethylpropanoyl chloride,
2,2-bis (fluoromethyl) propanoyl chloride,
3-chloro-2,2-dimethylpropionic acid,
2,2-bis (chloromethyl) propionic acid,
3,3-dichloro-2,2-dimethylpropionic acid,
3-fluoro-2,2-dimethylpropionic acid,
2,2-bis (fluoromethyl) propionic acid and the like.
[0041]
Carboxylic acids in which M represents a hydroxyl group in the formula (III) include compounds well known in the field of organic chemistry, and can be easily obtained by, for example, hydrolysis of esters, oxidation of alcohols, aldehydes, and ketones. Can be manufactured.
[0042]
The reaction of the above production method (a) can be carried out in a suitable diluent. Examples of the diluent used in this case include aliphatic, cycloaliphatic and aromatic hydrocarbons (in some cases chlorine). Such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, etc .; ethers, For example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM) and the like; ketones such as acetone, methyl ethyl ketone (MEK), methyl-isopropyl Ketones, methyl isobutyl ketone (MIBK), etc .; nitriles such as acetonitrile, propionitrile, etc .; esters such as ethyl acetate, amyl acetate, etc .; acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA) ), N-methylpyrrolidone, etc .; sulfone, sulfoxides such as dimethyl sulfoxide (DMSO), sulfolane, etc .; bases such as pyridine.
[0043]
The production method (a) can be performed in the presence of an acid binder or a condensing agent. Examples of the acid binder that can be used include inorganic bases, alkali metal hydrides and carbonates, such as sodium hydride, Lithium hydride, sodium carbonate, potassium carbonate, etc .; and organic bases such as tertiary amines, dialkylaminoanilines and pyridines such as triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), pyridine 4-dimethylaminopyridine (DMAP), 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU), and the like. In addition, as the condensing agent, carbodiimides; for example, N, N′-dicyclohexylcarbodiimide, N (3-dimethylaminopropyl) -N'- ethylcarbodiimide may be mentioned hydrochloric acid salts.
[0044]
The reaction of process (a) can be carried out within a substantially wide temperature range, but generally a temperature between about -20 and about 140 ° C, preferably between about 0 and about 100 ° C is suitable. In addition, the reaction is desirably performed under normal pressure, but may be operated under pressure or reduced pressure depending on circumstances.
[0045]
Further, in the formula (III), when M represents a hydroxyl group, the production method can be carried out by optionally adding an additive. Examples of additives that can be used include N-hydroxybenzotriazole and N-hydroxysuccinimide. 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine and the like.
[0046]
In carrying out the production method (a), for example, in a diluent such as tetrahydrofuran, 1 to 5 mol of the compound of (III) is reacted in the presence of 1 to 5 mol of triethylamine with respect to 1 mol of the compound of formula (II). To obtain the desired compound of formula (I).
[0047]
The active compound of the formula (I) of the present invention exhibits excellent herbicidal activity against various weeds as shown in the biological test examples described later, and can be used as a herbicide. As used herein, “weed” means all plants that grow in undesirable places in a broad sense. The compounds of the invention act as non-selective or selective herbicides depending on the concentration used. The active compounds according to the invention can be used, for example, between the following weeds and cultivated plants.
[0048]
In addition, as described above, the active compound of the formula (I) of the present invention is mixed with other herbicidal active compounds or safeners to obtain a more powerful herbicidal effect and selectivity as a mixed herbicidal composition. Can show.
[0049]
Dicotyledonous weeds belonging to the following genera: Sinapis, Leipidium, Galium, Stellaria, Chenopodium, Urtica, Candidae, A. ), S. pine, Portulaca, Xanthium, Ipomoea, Polygonum, Ambrosia, Cirrus, Sorghum, S. (Roripppa), Laurium, Stag beetle (V) ronica), Datura (Datura), violet pansy (Viola), Chishimaodoro (Galeopsis), poppy (Papaver), knapweed (Centaurea), galinsoga quadriradiata (Galinsoga), toothcup (Rotala), false pimpernel (Lindernia), and the like.Dicotyledonous plants belonging to the following genera: Cotton (Gossypium), soybean (Glycine), chard sugar beet (Beta), carrot (Daucus), common bean (Papirus), pea (Pisum), eggplant potato (Solanum), sweet potato (Linum) Japanese morning glory (Ipomoea), broad bean nanthagi (Vicia), tobacco (Nicotiana), tomato (Lycopersicon), peanut (Arachis), rape, cabbage cabbage (Brassica), akinonogeshi (Lactucurium) (Cucurbita) and the like.
[0050]
Monocotyledonous weeds belonging to the following genera: Echinochloa, Enokoro Awa (Setaria), Millet (Panicum), Meishi Shiba (Digitalia), Awagarie Timothy (Phleum), Strawberry Swag Suzumeno Katavilla (Poa), Ushikokegusa Toboshiga (Est) ), Bokumugi (Lolium), Vulture, Bromus, Oats, Oats (Avena), Cyperus, Papyrus, Shichitoui, Cyperus, Sorghum, Monguro Tentsuki (Fimbristylis), Omodaka Kwai (Sagitaria), Harii Krogwai (El) ocharis), bulrush, Ukiyagura-thick (Scirpus), Paspalum (Paspalum), platypus (Ischaemum), Agrostis (Agrostis), foxtail (Alopecurus) Giyougishiba (Cynodon) and the like.
[0051]
Monocotyledonous plants belonging to the following genera: Rice (Oryza), corn hop corn (Zea), wheat (Triticum), barley (Hordeum), oats (Ovena), rye (Secale), sorghum, Panicum, sugarcane -Wasebana (Saccharum), pineapple (Ananas), asparagus (Asparagus), leek and leek (Allium), etc.
[0052]
The active compound of the formula (I) and the mixed herbicidal composition of the present invention can be used particularly for paddy weeds. Specific examples of paddy field weeds that can be controlled using the compound of the present invention and the mixed herbicidal composition include, for example, red oak rush (Rotala indica Koehne), azena (Lindernia Procumbens Philcox), , Hiramshiro (Potamogeton distinctus A. Benn), Ezotine triandra Schk, seri (Oenanthe jawanica), Echnochlo oryzicola Vasing, Koch. Lee (Eleocharis Kuroguwai Ohwi), smallflower umbrellaplant (Cyperus difformis L.), Cyperus (Cyperus serotinus Rottboel), arrowhead (Sagittaria pygmaea Miq), alisma canaliculatum (Alisma canaliculatum A. Br. Et Bouche), cited such as bulrush (Scirpus juncoides Roxburgh) be able to. Moreover, the active compound and mixed herbicidal composition of the said Formula (I) of this invention can be used with respect to the weed which shows tolerance with respect to a sulfonylurea type herbicide. The resistant weeds, specifically, for example, Rotala indica (Rotala indica Koehne), false pimpernel (Lindernia Procumbens Philcox), Amerikaazena (Lindernia dubia L. PENNEL), Taketoazena (Lindernia var. Dubia Pennell), Azetougarashi (Lindernia angustifolia Wettstein ), Echotine triandra Schk, Mizuoria korsakuii REGEL & MAACK, Konagi (Monochoria vaginalis Presl), Firefly (Scirphus juncoid) Kill. However, the use of the active compound of the formula (I) and the mixed herbicide composition of the present invention is not limited to the use against these weeds, but weeds other than other paddy weeds and sulfonylurea herbicide-resistant weeds. The same applies to the above.
[0053]
The use of the compound of the present invention is not limited to the above-mentioned plants, but can be applied to other plants as well. Further, depending on the concentration used, the active compound of the present invention can control weeds non-selectively, and can be used, for example, in industrial sites such as factories, railway tracks, roads, plantations, non-plants, etc. it can. Furthermore, the active compounds of the present invention can be used for weed control in perennial plant cultivation, for example, afforestation, ornamental plantation, orchard, vineyard, citrus orchard, nut orchard, banana cultivation Can be applied to farms, coffee farms, tea farms, rubber farms, Guinea oil palm farms, cocoa farms, orchards, hop farms, etc. It can also be applied for control.
[0054]
The active compound and the mixed herbicidal composition of the present invention can be made into a usual preparation form when actually used. Examples of the dosage form include liquids, wettable powders, emulsions, suspensions, powders, granular wettable powders, tablets, granules, concentrated suspension emulsions, microcapsules in polymer substances, jumbo drugs, etc. Can be mentioned.
[0055]
These formulations can be prepared in a manner known per se, for example, by adding the active compound to a developing agent, ie a liquid or solid diluent or carrier, and optionally a surfactant, ie an emulsifier and / or Alternatively, it can be prepared by mixing with a dispersant and / or foam former.
[0056]
Liquid diluents or carriers include, for example, aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride, methylene chloride) Etc.), aliphatic hydrocarbons [for example, cyclohexane, paraffins (for example, mineral oil fraction, etc.)], alcohols (for example, butanol, glycol, etc.) and their ethers, esters, etc., ketones (for example, acetone, Methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), strong polar solvents (eg, dimethylformamide, dimethyl sulfoxide, etc.), water and the like. When water is used as the developing agent, for example, an organic solvent can be used as an auxiliary solvent.
[0057]
Solid diluents or carriers include, for example, ground natural minerals (eg, kaolin, clay, talc, chalk, quartz, attapul guide, montmorillonite, diatomaceous earth, etc.), ground synthetic minerals (eg, highly dispersed silicic acid, alumina, silicic acid) Salt, etc.). Solid carriers for granules include crushed and separated rocks (eg, calcite, marble, pumice, gypsum, dolomite, etc.), synthetic grains of inorganic and organic powders, and organic substances (eg sawdust, coconut palm) Corn, corn cobs, tobacco stems, etc.).
[0058]
Examples of the emulsifier and / or foaming agent include nonionic and anionic emulsifiers [for example, polyoxyethylene fatty acid ester, polyoxyethylene fatty acid alcohol ether (for example, alkylaryl polyglycol ether, alkyl sulfonate, alkyl sulfate, Aryl sulfonates, etc.)], albumin hydrolysis products, and the like.
[0059]
Dispersants include, for example, lignin sulfite waste liquor and methylcellulose.
[0060]
Adhesives can also be used in preparations (powder, granules, emulsions), such as carboxymethylcellulose, natural and synthetic polymers (eg gum arabic, polyvinyl alcohol, polyvinyl acetate, etc.). Can do.
[0061]
Colorants can also be used, such as inorganic pigments (eg, iron oxide, titanium oxide, Prussian blue, etc.), alizarin dyes, organic dyes such as azo dyes or metal phthalocyanine dyes, iron, A trace element such as a metal salt such as manganese, boron, copper, cobalt, molybdenum, or zinc can be used.
[0062]
The formulations generally can contain from 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of the active compound of formula (I).
[0063]
The active compounds of the formula (I) according to the invention can be used for controlling weeds by themselves or in their formulation, and the mixed herbicidal compositions with known herbicides can be used in advance. It may be prepared in a typical formulation form or may be prepared by tank mixing at the time of use. Specific examples of herbicides that can be used in combination with the compound of formula (I) of the present invention as a mixed herbicide composition include the following herbicides represented by general names.
[0064]
Acetamide herbicides: for example, pretilachlor, butachlor, tenyl chlor, alachlor, etc .;
Amide-based herbicides: for example, chromeprop, ethozanide, etc .;
Benzofuran herbicides: for example, benfrate
Indandione herbicides: for example, indanophan, etc .;
Pyrazole herbicides: for example, pyrazolate, benzophenap, pyrazoxifene, etc .;
Oxazinone herbicides: for example, oxadichrome mephone;
Sulfonylurea herbicides: for example, bensulfuron methyl, azimusulfuron, imazosulfuron, pyrazosulfuron ethyl, cyclosulfamuron, ethoxysulfuron, halosulfuron methyl, etc .;
Thiocarbamate herbicides: for example, thiobencarb, molinate, pyributycarb, etc .;
Triazine herbicides: for example, dimetamethrin, simethrin, etc .;
Triazole herbicides: for example, cavenstrol, etc .;
Quinoline herbicides: for example, quinclolac and the like;
Isoxazole herbicides: for example, isoxaflutol and the like;
Dithiophosphate herbicides: for example, anilophos and the like;
Oxyacetamide herbicides: for example, mefenacet, flufenacet, etc .;
Tetrazolinone herbicides: for example, fentolazamide;
Dicarboximide herbicides: for example, pentoxazone and the like;
Trione herbicides: for example, sulcotrione, benzobicyclone, etc .;
Phenoxypropinate herbicide: for example, cihalohop butyl, etc .;
Benzoic acid herbicides: for example, pyriminobac-methyl, etc .;
Diphenyl ether herbicides: for example, chloromethoxyphene, oxyfluorfen, etc .;
Pyridine dicarbothioate herbicides: for example, dithiopyr etc .;
Phenoxy herbicide: for example, MCPA, MCPB, etc .;
Urea herbicides: for example, Daimlon, Cumylron, etc .;
Naphthalenedione herbicides: for example, quinoclamin, etc .;
Isoxazolidinone herbicides: for example, clomazone.
[0065]
The active compounds are known herbicides described in “Pesticide Manual”, 2000, published by British Crop Protect Council.
[0066]
In addition, when the active compound of the formula (I) of the present invention is mixed with a safener, this mixing reduces the safeguard, provides a broader spectrum of weed control, and has a wider application as a selective herbicide. can do.
[0067]
Examples of the safeners include the following compounds represented by general names or development codes.
[0068]
AD-67, BAS-145138, Benoxacol, croquintoset mexil, ciomethrinyl, 2,4-D, DKA-24, dichlormid, diemron, fenchlorim, fenchlorazole ethyl, flurazole, fluxophenim, flirazole, isoxadifenethyl , Mefenpyr diethyl, MG-191, naphthalic anhydride, oxabetrinyl, PPG-1292, R-29148, and the like.
[0069]
The above-mentioned safeners are also described in “Pesticide Manual”, 2000, published by British Crop Protect Council.
[0070]
Further, the mixed herbicidal composition comprising the compound of the formula (I) of the present invention and the herbicide can be further mixed with the above-mentioned phytotoxicity reducing agent. A broader spectrum of weed control is provided, which can make the application as a selective herbicide wider.
[0071]
Surprisingly, some mixed herbicidal compositions of the compounds of the invention with known herbicides and / or safeners can also exhibit a synergistic effect.
[0072]
When using the active compounds of the formula (I) according to the invention, whether they are used directly as they are or in the form of preparations such as preparations for spraying, emulsions, tablets, suspensions, powders, pastes, granules Or can be used in a use form prepared by further dilution. The active compound of the present invention can be applied, for example, by methods such as liquid spraying, spraying, atomizing, and dusting.
[0073]
The active compounds of the formula (I) according to the invention can be used at any stage before and after germination of plants. They can also be incorporated into the soil before sowing.
[0074]
The application rates of the active compounds according to the invention can be varied within a substantial range. It is fundamentally different depending on the nature of the effect to be desired. When used as a herbicide, the application rate is, for example, about 0.01 to about 4 kg, preferably about 0.05 to about 3 kg as an active compound per hectare.
[0075]
Next, the production and use of the compound of the present invention will be described more specifically by the following examples, but the present invention should not be limited to these.
[0076]
【Example】
Compound production examples
Synthesis example 1
[0077]
Embedded image
2,2-bis (chloromethyl) propanoyl chloride (0.34 g) was dissolved in THF (5 ml) and dissolved in 5-N-methylamino-3- (3-trifluoromethylphenyl) -4-thiazolidinone ( 0.50 g) and triethylamine (0.18 g) in THF (10 ml) were added dropwise at room temperature, and the mixture was stirred for 3 hours. After the reaction, cold water was added and the mixture was extracted with ethyl acetate (50 ml), washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained by distilling off ethyl acetate was purified by silica gel column chromatography (elution solvent; ethyl acetate; hexane = 1: 1), and the desired 5- {2,2-bis (chloromethyl) propanoyl- N-methyl} amino-3- (3-trifluoromethylphenyl) -4-thiazolidinone (0.64 g) was obtained. mp: 115-116 ° C
The compounds obtained by operating according to the production method of the compound of formula (I) of the present invention exemplified in Synthesis Example 1 are shown in Table 1 below together with the compound synthesized in Synthesis Example 1.
[0079]
The compound of formula (I) of the present invention is represented by the formula
[0080]
Embedded image
Table 1 shows examples of compounds in which
[0082]
In Table 1, Me represents methyl and t-Bu represents tert-butyl.
[0083]
Table 1
[0084]
[Table 1]
[0086]
Embedded image
5-Chloro-3- (3-trifluoromethylphenyl) -4-thiazolidinone (11.0 g) was dissolved in dichloromethane (30 ml) and dissolved in 40% aqueous methylamine (45.5 g), sodium iodide (0 .59 g), triethylbenzylammonium chloride (0.89 g) and dichloromethane (30 ml) were added dropwise under ice cooling, and the mixture was stirred for 1 hour under ice cooling. After the reaction, the mixture was extracted with dichloromethane (50 ml), washed with saturated brine, and dried over anhydrous magnesium sulfate. Dichloromethane was distilled off, and the resulting residue was purified by silica gel column chromatography (elution solvent; ethyl acetate: hexane = 1: 1 to 2: 1) to give 5-N-methylamino-3- (3-trimethyl). Fluoromethylphenyl) -4-thiazolidinone (5.80 g) was obtained. mp: 88-89 ° C
Biological test example
Test example 1： Weeding effect test for paddy weeds
Preparation of active compound formulations:
Carrier: dimethylformamide (DMF) 5 parts by weight
Emulsifier: 1 part by weight of benzyloxypolyglycol ether
Active substance preparations are obtained as emulsions by mixing 1 part by weight of the active compound with the above-mentioned amounts of carrier and emulsifier. Dilute the prescribed amount of the preparation with water.
Test method:
500cm packed with paddy soil in a greenhouse2Three rice seedlings (variety: Nipponbare) at 2.5 leaf stage (plant height: 15 cm) were planted in a pot. Next, various seedlings or tubers of fly, tuber, firefly, oyster, broad-leaved weed (Azena, Kikashigusa, Mizohakobe, Himeisohagi, Abnomome, etc.), Mizugayatsuri, Urikawa were inoculated and submerged about 2-3 cm.
[0088]
Five days after the rice transplantation, the surface treatment was carried out with a predetermined dilution of each active compound preparation prepared according to the above preparation method. After the treatment, the submerged state was maintained at 3 cm, and the herbicidal effect was investigated 3 weeks after spraying. In addition, the evaluation of the herbicidal effect was performed assuming that complete withering was 100% and 0% was not.
result:
As a result, as representative examples, the compound numbers 11, 49, 51, 52, 54, 57, 61, 168, 171, 176, 269 and 277 all have a drug dose (active ingredient amount) of 0.125 kg / Ha showed a sufficient herbicidal effect on paddy weeds and safety for transplanted rice.
Test example 2: Pre-emergence soil treatment test for upland weeds
Test method:
120cm packed with field soil in a greenhouse2The surface layer of the pot was seeded with various seeds of barnyard grass, green foxtail, Aoubiyu and Inuta, and a diluted solution of a predetermined amount prepared in the same manner as in Test Example 1 was uniformly sprayed on the soil surface of each test pot. The degree of herbicidal effect was investigated 4 weeks after spraying.
result:
As a result, as representative examples, all of the compounds of Compound Nos. 168, 171, 176, 261, and 281 have a drug dose (active ingredient amount) of 0.06 kg / ha, and are 90% against that of Japanese millet, Enocologosa, Aoubi and Inuta. % Of herbicidal activity.
Test example 3: Post-emergence foliar treatment test for upland weeds
Test method:
120cm packed with field soil in a greenhouse2The pots were seeded with shrimp, sorghum, green abalone and Inuta seeds and covered with soil. Ten days after sowing cover (weeds average 2 leaf stages), a diluted solution of a predetermined dosage prepared in the same manner as in Test Example 1 was uniformly sprayed on the foliage of each test pot. The degree of herbicidal effect was investigated 3 weeks after spraying.
result:
As a result, as representative examples, all of the compounds of Compound Nos. 45, 61, 265, and 281 have a drug dose (active ingredient amount) of 0.5 kg / ha, and are 90% or more with respect to Japanese millet, Enocologosa, Aoubi and Inuta. Showed herbicidal activity.
[0089]
Formulation examples
Formulation Example 1(Granule)
This invention compound No. Add water (25 parts) to a mixture of 52 (10 parts), bentonite (montmorillonite) (30 parts), talc (talc) (58 parts) and lignin sulfonate (2 parts). It is made into granules by drying at 40-50 ° C. as granules of 10-40 mesh by a granulator.
[0090]
Formulation Example 2(Granule)
Clay mineral grains (95 parts) having a particle size distribution of 0.2 to 2 mm are placed in a rotary mixer, and under rotation, the present compound No. 49 (5 parts) was sprayed and moistened evenly, and then dried at 40 to 50 ° C. to give granules.
[0091]
Formulation Example 3(emulsion)
This invention compound No. 261 (30 parts), xylene (5 parts), polyoxyethylene alkylphenyl ether (8 parts) and calcium alkylbenzenesulfonate (7 parts) are mixed and stirred to obtain an emulsion.
[0092]
Formulation Example 4(Wettable powder)
This invention compound No. 281 (15 parts), mixture of white carbon (hydrous non-crystalline oxysilicate fine powder) and powdered clay (1: 5) (80 parts), sodium alkylbenzenesulfonate (2 parts) and sodium alkylnaphthalenesulfonate formalin polymerization The product (3 parts) is mixed with powder to obtain a wettable powder.
[0093]
Formulation Example 5(Hydrated granules)
This invention compound No. 176 (20 parts), sodium lignin sulfonate (30 parts), bentonite (15 parts) and calcined diatomaceous earth powder (35 parts), add water, extrude and dry with a 0.3 mm screen, Use hydrated granules.
[0094]
【The invention's effect】
The novel azolidine derivative of the present invention has excellent properties as a herbicide, as is apparent from the above biological test examples.
Claims (4)
Ｒ１はハロゲン、アルキル、アルコキシ、ハロアルキル、ハロアルコキシ、ハロアルキルチオ又はハロアルキレンジオキシを示し、
ｍは０、１、２、３、４又は５を示し、
ｍが２、３、４又は５を示すとき、２〜５個のＲ１は同一もしくは相異なり、
Ｒ２はアルキルを示し、
Ｘはアルキリデン、酸素原子又は硫黄原子を示し、そして
Ａは基
Ｑはアルキルを示し、
Ｑ−ｈａｌはハロアルキルを示し、そして
Ｈａｌはハロゲンを示す、
で表されるアゾリジン誘導体。formula
R 1 represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkylthio or haloalkylenedioxy,
m represents 0, 1, 2, 3, 4 or 5;
when m is 2, 3, 4 or 5, 2-5 R 1 are the same or different;
R 2 represents alkyl,
X represents an alkylidene, oxygen atom or sulfur atom, and A represents a group
Q-hal represents haloalkyl and Hal represents halogen;
An azolidine derivative represented by:
ｍが１、２又は３を示し、
Ｒ２がメチルを示し、
Ｘがメチレン、酸素原子又は硫黄原子を示し、そして
Ａが基
ＱがＣ１−４アルキルを示し、
Ｑ−ｈａｌがＣ１−４ハロアルキルを示し、そして
Ｈａｌがクロロ又はブロモを示す、
請求項１に記載の化合物。R 1 is fluoro, chloro, bromo, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, C 1-4 haloalkylthio or C 1-4 haloalkylenedioxy. Show
m represents 1, 2 or 3,
R 2 represents methyl,
X represents a methylene, oxygen atom or sulfur atom, and A represents a group
Q-hal represents C 1-4 haloalkyl and Hal represents chloro or bromo;
The compound of claim 1.
ｍが１、２又は３を示し、
ｍが１を示すとき、Ｒ１はフェニル基の３位に結合し、
ｍが２を示すとき、２個のＲ１はフェニル基の３位及び４位に結合するか又は３位及び５位に結合し、且つ２個のＲ１は同一もしくは相異なり、
ｍが３を示すとき、３個のＲ１はフェニル基の３位、４位及び５位に結合し、且つ３個のＲ１は同一もしくは相異なり、
Ｒ２がメチルを示し、
Ｘがメチレン、酸素原子又は硫黄原子を示し、そして
Ａが基
Ｑがメチル又はｔｅｒｔ−ブチルを示し、
Ｑ−ｈａｌがフルオロメチル、クロロメチル、ジクロロメチル又はブロモメチルを示し、そして
Ｈａｌがクロロ又はブロモを示す、
請求項１又は２に記載の化合物。R 1 is fluoro, chloro, bromo, methyl, methoxy, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, difluoromethoxy, chlorodifluoromethoxy, trifluoromethoxy, trifluoroethoxy, dichloromethoxy, difluoromethylthio, trifluoromethylthio, difluoro Represents methylenedioxy or tetrafluoroethylenedioxy,
m represents 1, 2 or 3,
when m is 1, R 1 is bonded to the 3-position of the phenyl group;
When m represents 2, two R 1 is attached to, or positions 3 and 5 are attached to the 3-position and 4-position of the phenyl group, and two R 1 are identical or different,
when m represents 3, three R 1 are bonded to the 3-position, 4-position and 5-position of the phenyl group, and the three R 1 are the same or different;
R 2 represents methyl,
X represents a methylene, oxygen atom or sulfur atom, and A represents a group
Q-hal represents fluoromethyl, chloromethyl, dichloromethyl or bromomethyl, and Hal represents chloro or bromo;
The compound according to claim 1 or 2.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003182274A JP2005015390A (en) | 2003-06-26 | 2003-06-26 | Azolidine derivative and herbicide |
| ARP040102060 AR044695A1 (en) | 2003-06-26 | 2004-06-14 | DERIVATIVES OF AZOLIDINE, USEFUL AS HERBICIDES. |
| PCT/EP2004/006367 WO2005000824A1 (en) | 2003-06-26 | 2004-06-14 | Lazolidine derivatives as herbicidal agents |
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| JP2003182274A JP2005015390A (en) | 2003-06-26 | 2003-06-26 | Azolidine derivative and herbicide |
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| JP (1) | JP2005015390A (en) |
| AR (1) | AR044695A1 (en) |
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|---|---|---|---|---|
| JPWO2005095327A1 (en) * | 2004-03-31 | 2008-02-21 | 味の素株式会社 | Aniline derivative |
| JPWO2017002201A1 (en) * | 2015-06-30 | 2018-05-31 | 株式会社エス・ディー・エス バイオテック | Cyclopropanecarboxylic acid amide compounds and herbicides containing them |
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| WO2016196738A1 (en) | 2015-06-02 | 2016-12-08 | Monsanto Technology Llc | Compositions and methods for delivery of a polynucleotide into a plant |
| EP3302030A4 (en) | 2015-06-03 | 2019-04-24 | Monsanto Technology LLC | METHODS AND COMPOSITIONS FOR THE INTRODUCTION OF NUCLEIC ACIDS IN PLANTS |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU696084B2 (en) * | 1994-06-02 | 1998-09-03 | Zeneca Limited | Substituted pyrrolidone, thiazolidones or oxazolidones as herbicides |
| GB9524667D0 (en) * | 1995-12-01 | 1996-01-31 | Zeneca Agrochemicals | Herbicides |
| GB9822116D0 (en) * | 1998-10-09 | 1998-12-02 | Zeneca Ltd | Herbicides |
-
2003
- 2003-06-26 JP JP2003182274A patent/JP2005015390A/en active Pending
-
2004
- 2004-06-14 WO PCT/EP2004/006367 patent/WO2005000824A1/en not_active Ceased
- 2004-06-14 AR ARP040102060 patent/AR044695A1/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005095327A1 (en) * | 2004-03-31 | 2008-02-21 | 味の素株式会社 | Aniline derivative |
| JP4775259B2 (en) * | 2004-03-31 | 2011-09-21 | 味の素株式会社 | Aniline derivative |
| JPWO2017002201A1 (en) * | 2015-06-30 | 2018-05-31 | 株式会社エス・ディー・エス バイオテック | Cyclopropanecarboxylic acid amide compounds and herbicides containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005000824A1 (en) | 2005-01-06 |
| AR044695A1 (en) | 2005-09-21 |
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