JP4970950B2 - 3−トリアゾリルフェニルスルフィド誘導体及びそれを有効成分として含有する殺虫・殺ダニ・殺線虫剤 - Google Patents
3−トリアゾリルフェニルスルフィド誘導体及びそれを有効成分として含有する殺虫・殺ダニ・殺線虫剤 Download PDFInfo
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- JP4970950B2 JP4970950B2 JP2006543069A JP2006543069A JP4970950B2 JP 4970950 B2 JP4970950 B2 JP 4970950B2 JP 2006543069 A JP2006543069 A JP 2006543069A JP 2006543069 A JP2006543069 A JP 2006543069A JP 4970950 B2 JP4970950 B2 JP 4970950B2
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- AAXFXXDVLCDKPL-UHFFFAOYSA-N 4-[3-[3-(2h-triazol-4-yl)phenyl]sulfanylphenyl]-2h-triazole Chemical class C=1C=CC(C=2N=NNC=2)=CC=1SC(C=1)=CC=CC=1C1=CNN=N1 AAXFXXDVLCDKPL-UHFFFAOYSA-N 0.000 title claims description 22
- 239000004480 active ingredient Substances 0.000 title claims description 15
- 230000000895 acaricidal effect Effects 0.000 title claims description 14
- 239000000642 acaricide Substances 0.000 title claims description 12
- 239000002917 insecticide Substances 0.000 title claims description 12
- 239000005645 nematicide Substances 0.000 title claims description 11
- -1 3-triazolyl naphthoylmethyl Chemical group 0.000 claims description 102
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 5
- 150000003568 thioethers Chemical class 0.000 claims description 5
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000008901 benefit Effects 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 230000001548 androgenic effect Effects 0.000 claims 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 150000001875 compounds Chemical group 0.000 description 244
- 238000006243 chemical reaction Methods 0.000 description 186
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 85
- 239000002904 solvent Substances 0.000 description 83
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 79
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 46
- 238000004519 manufacturing process Methods 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 238000010992 reflux Methods 0.000 description 41
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 40
- 239000002585 base Substances 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 38
- 241000607479 Yersinia pestis Species 0.000 description 37
- 239000000203 mixture Substances 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 34
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 33
- 239000000543 intermediate Substances 0.000 description 32
- 230000035484 reaction time Effects 0.000 description 31
- 150000001298 alcohols Chemical class 0.000 description 30
- 239000000758 substrate Substances 0.000 description 30
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 22
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 22
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 22
- 150000002170 ethers Chemical class 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 239000008096 xylene Substances 0.000 description 22
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 20
- 239000012046 mixed solvent Substances 0.000 description 20
- 239000002798 polar solvent Substances 0.000 description 20
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 19
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 17
- 230000008569 process Effects 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 241000244206 Nematoda Species 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 150000008282 halocarbons Chemical class 0.000 description 15
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 14
- 229910052783 alkali metal Inorganic materials 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- 235000011181 potassium carbonates Nutrition 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 13
- 150000002576 ketones Chemical class 0.000 description 13
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 150000003222 pyridines Chemical class 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 241000254173 Coleoptera Species 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 241001454295 Tetranychidae Species 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 241000238631 Hexapoda Species 0.000 description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 10
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 10
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 10
- 239000000920 calcium hydroxide Substances 0.000 description 10
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 10
- 150000007529 inorganic bases Chemical class 0.000 description 10
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 10
- 239000000347 magnesium hydroxide Substances 0.000 description 10
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 10
- 229910052987 metal hydride Inorganic materials 0.000 description 10
- 150000004681 metal hydrides Chemical class 0.000 description 10
- 150000002825 nitriles Chemical class 0.000 description 10
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 10
- 235000015497 potassium bicarbonate Nutrition 0.000 description 10
- 239000011736 potassium bicarbonate Substances 0.000 description 10
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 10
- 229910000105 potassium hydride Inorganic materials 0.000 description 10
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 10
- 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 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 9
- 150000008041 alkali metal carbonates Chemical class 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 241000255925 Diptera Species 0.000 description 8
- 241000258937 Hemiptera Species 0.000 description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 description 8
- 235000010755 mineral Nutrition 0.000 description 8
- 239000011707 mineral Substances 0.000 description 8
- 150000007530 organic bases Chemical class 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 7
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
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- 0 CC(C(*=C1*)=**1C(C(C)=C(*N(C)C)C(*)*1)=C1NC)N Chemical compound CC(C(*=C1*)=**1C(C(C)=C(*N(C)C)C(*)*1)=C1NC)N 0.000 description 6
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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 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
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- 239000003377 acid catalyst Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
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- 239000011259 mixed solution Substances 0.000 description 6
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- 239000011591 potassium Substances 0.000 description 6
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- 150000003839 salts Chemical class 0.000 description 6
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
- RSZVVMOFNZNLLE-UHFFFAOYSA-N 2-[5-[1-[1-[5-[5-amino-3-(trifluoromethyl)-1,2,4-triazol-1-yl]-4-fluoro-2-methylphenyl]-2,2,2-trifluoroethyl]sulfanyl-2,2,2-trifluoroethyl]-2-fluoro-4-methylphenyl]-5-(trifluoromethyl)-1,2,4-triazol-3-amine Chemical compound CC1=CC(F)=C(N2C(=NC(=N2)C(F)(F)F)N)C=C1C(C(F)(F)F)SC(C(F)(F)F)C(C(=CC=1F)C)=CC=1N1N=C(C(F)(F)F)N=C1N RSZVVMOFNZNLLE-UHFFFAOYSA-N 0.000 description 5
- 241001414720 Cicadellidae Species 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- DOWDPLZXDNSXOQ-UHFFFAOYSA-N 5-amino-4-fluoro-2-methylbenzenethiol Chemical compound CC1=CC(F)=C(N)C=C1S DOWDPLZXDNSXOQ-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
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- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 125000005323 thioketone group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- SLVAEVYIJHDKRO-UHFFFAOYSA-N trifluoromethanesulfonyl fluoride Chemical compound FC(F)(F)S(F)(=O)=O SLVAEVYIJHDKRO-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/36—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
- C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Description
(1)一般式[I]で表される3−トリアゾリルフェニルスルフィド誘導体:
nは1であり、
A1は、C1〜C6アルキル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)、C1〜C6アルキルチオ基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)、又はC1〜C6アルキルスルフィニル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)であり、
A3は、−NR2R3基、又は−N(COR2)R3基であり、R2及びR3は、互いに独立して、水素原子、又はC1〜C6アルキル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)であり、
B2はハロゲン原子であり、
B4はC1〜C6アルキル基である。
(2)Rがトリフルオロエチル基であり、
nが1であり、
A1がC1〜C6アルキル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)、C1〜C6アルキルチオ基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)、又はC1〜C6アルキルスルフィニル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)であり、
A3がアミノ基であり、
B2がハロゲン原子であり、
B4がC1〜C6アルキル基である
前記(1)記載の3−トリアゾリルフェニルスルフィド誘導体。
(3)A1がトリフルオロメチル基であり、
A3がメチルアミノ基、トリフルオロアセチルアミノ基である
前記(1)記載の3−トリアゾリルフェニルスルフィド誘導体。
(4)A1がトリフルオロメチル基、トリフルオロメチルチオ基、又は2,2,2−トリフルオロエチルスルフィニル基であり、
A3がアミノ基である前記(2)記載の3−トリアゾリルフェニルスルフィド誘導体。
(5)前記(1)乃至(4)のいずれかに記載の3−トリアゾリルフェニルスルフィド誘導体の製造中間体である一般式[I−a](式中、Rはトリフルオロエチル基であり、B2はハロゲン原子であり、B4はC1〜C6アルキル基である)で表されるアニリン誘導体。
(7)前記(1)1乃至(4)のいずれかに記載の3−トリアゾリルフェニルスルフィド誘導体を有効成分として含有することを特徴とする農園芸用殺虫・殺ダニ剤・殺線虫剤。
特に本発明化合物は農園芸有害生物であるナミハダニ、カンザワハダニ、ミカンハダニ等に代表されるハダニ類、コナガ、ニカメイガ、シロイチモジヨトウ等に代表される鱗翅目害虫、トビイロウンカ、ツマグロヨコバイ、ワタアブラムシ等に代表される半翅目害虫、アズキゾウムシ等に代表される鞘翅目害虫及びサツマイモネコブセンチュウ等の線虫類に卓効を示し、浸透移行性に優れるため、土壌処理による安全で省力的施用方法が可能である。
ハロゲン原子とは、フッ素原子、塩素原子、臭素原子、ヨウ素原子を示す。
C1〜C6等の表記は、これに続く置換基の炭素数が、この場合では1〜6であることを示している。
Pr :n−プロピル、 Pr−i :イソプロピル、
Pr−c :シクロプロピル、 Bu :n−ブチル、
Bu−i :イソブチル、 Bu−s :sec−ブチル、
Bu−t :tert−ブチル、 Bu−c :シクロブチル、
Pen :n−ペンチル、 Pen−i:イソペンチル、
Pen−c:シクロペンチル、 Hex−c:シクロヘキシル、
Ph :フェニル Py :ピリジル
例えばPh−4−Clとは4−クロロフェニル、3−Py−6−Clとは6−クロロ−3−ピリジルを示す。
すなわち、一般式[I−1]の3−トリアゾリルフェニルスルフィド誘導体は一般式[II]の化合物と一般式[III]の化合物とを、溶媒中、塩基の存在下又はラジカル開始剤の存在下で反応させることにより製造することができる。
一般式[I−1]の化合物の原料は、製造法1で使用した一般式[II]の化合物の酸化的二量体である一般式[IV]の化合物を使用することもできる。
すなわち、目的とする一般式[I−1]の3−トリアゾリルフェニルスルフィド誘導体は一般式[IV]の化合物と一般式[V]の化合物とを、溶媒中、ラジカル開始剤の存在下で反応させることにより製造することができる。
一般式[I−2]の化合物は下記に例示する反応式からなる方法によって製造することができる。
すなわち、一般式[I−2]の化合物は一般式[VI]の化合物と一般式[VII]の化合物とを、溶媒中、塩基の存在下で反応させることにより製造することができる。
一般式[I−2]の化合物は、下記に例示する置換反応からなる方法によっても製造することができる。
すなわち、一般式[I−2]の3−トリアゾリルフェニルスルフィド誘導体は一般式[IX]の化合物と一般式[X]の化合物とを、溶媒中、塩基又は酸化銅(I)の存在下で反応させることにより製造することができる。
本発明化合物である一般式[I]の化合物は下記に例示する反応式からなる方法によって製造することができる。
すなわち、一般式[I]で表される本発明化合物は一般式[VI]の化合物と一般式[VIII]の化合物及び無水銅塩とを、溶媒中、有機塩基の存在下で反応させることにより製造することができる。
有機塩基の使用量は、一般式[VI]の化合物1モルに対して1〜5モルの範囲から適宜選択すればよく、好ましくは1.2〜4.4モルである。
反応時間は反応温度、反応基質、反応量等により異なるが、通常8〜48時間である。
一般式[I−1]の化合物は下記に例示する反応式からなる方法によっても製造することができる。
すなわち、目的とする一般式[I−1]の3−トリアゾリルフェニルスルフィド誘導体は一般式[XI]の化合物を、溶媒中、常法[鉱酸(塩酸及び硫酸等を例示できる。)と亜硝酸塩もしくは亜硝酸アルキルエステルを用いる方法]にてジアゾニウム塩とした後、一般式[XII]のメルカプタンの塩又は一般式[XIII]のジスルフィド類と反応させることにより製造することができる。
反応時間は反応温度、反応基質、反応量等により異なるが、通常10分〜20時間である。
本発明化合物である一般式[I]の化合物は下記に例示する反応式からなる方法によっても製造することができる。
すなわち、一般式[I]の本発明化合物は一般式[XIV]の化合物と一般式[XV−1]又は一般式[XV−2]の化合物とを、溶媒中、塩基の存在下で反応させることにより製造することができる。
本工程で使用するアンモニア水の使用量は、一般式[XIV]の化合物1モルに対して1〜10モルの範囲から適宜選択すればよく、好ましくは2.0〜5.0モルである。
反応温度は−30℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは−10℃〜100℃の範囲で行うのがよい。
反応時間は反応温度、反応基質、反応量等により異なるが、通常10分〜20時間である。
また、本工程で使用する一般式[XV−3]の化合物及び一般式[XV−4]の化合物の使用量は、一般式[XIV−1]の化合物1モルに対して1モル〜大過剰の範囲であり、好ましくは1.0〜2.0モルである。
反応時間は反応温度、反応基質、反応量等により異なるが、通常10分〜20時間である。
(工程3)
一般式[I]の本発明化合物は一般式[XVI−1]の化合物と酸ハロゲン化物及び酸無水物等から誘導される一般式[XVII−1]の化合物と[XVIII]の化合物とを反応させることにより製造することができる。
反応時間は反応温度、反応基質、反応量等により異なるが、通常10分〜20時間である。
また、目的とする一般式[I−3]の3−トリアゾリルフェニルスルフィド誘導体は一般式[XVI−2]の化合物と二硫化炭素とハロゲン化アルキル等から誘導される一般式[XVII−2]の化合物と[XVIII]の化合物を反応させることにより製造することができる。
反応温度は−30℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは−10℃〜100℃の範囲で行うのがよい。
反応時間は反応温度、反応基質、反応量等により異なるが、通常10分〜20時間である。
一般式[I−1]の化合物は一般式[XIX]の化合物と金属又は有機金属化合物を反応させた後、一般式[XX]又は一般式[XIII]の化合物とを反応させることにより製造することができる。
<製造方法10>
一般式[I−4]の本発明化合物は一般式[I−1]の化合物と酸化剤とを、触媒存在下又は非存在下で反応させることにより製造することができる。
触媒の使用量は一般式[I−1]1モルに対して0〜1モルの範囲から適宜選択すればよく、好ましくは0.01〜0.1モルである。
反応時間は反応温度、反応基質、反応量等により異なるが、通常10分〜20時間である。
一般式[I]の本発明化合物は3−トリアゾリルフェニルスルフィド誘導体を一般的に知られている方法により官能基変換を行うことで製造することができる。
一般式[I]の本発明化合物は、一般式[I−3]の本発明化合物と親電子試薬とを、溶媒の存在下又は非存在下、塩基の存在下又は非存在下、酸の存在下又は非存在下、脱水縮合剤の存在下又は非存在下で、反応させることにより製造することができる。
本工程で使用できるヘテロ環カルボン酸としては例えば、3−ピリジンカルボン酸、チオフェンカルボン酸等があげられる。
本工程で使用できるヘテロ環カルボン酸ハライドとしては例えば、3−ピリジンカルボン酸クロリド、チオフェンカルボン酸クロリド等があげられる。
本工程で使用できる脂肪族カルボン酸ハライドとしては例えば、アセチルクロリド、プロピオン酸クロリド等があげられる。
本工程で使用できるアルコール類としては例えば、メタノール、エタノール、ベンジルアルコール等があげられる。
親電子試薬の使用量は、一般式[I−3]の化合物1モルに対して、1〜100モルの範囲から適宜選択すればよく、好ましくは1〜10モルであり、さらに好ましくは1〜3モルである。
一般式[I]の本発明化合物は、一般式[I−5]の化合物と一般式[I−7]で表される化合物とを塩基存在下又は非存在下、溶媒存在下、反応させることにより製造することができる。
一般式[I]で表される本発明化合物は一般式[I−6]の化合物とアミン類、カルボン酸類、アルコール類とを、溶媒存在下又は非存在化、反応させることにより製造することができる。
製造中間体[II]及び[IV]の合成
一般式[II]及び[IV]の化合物は下記のように合成することができる。もちろん、酸化還元反応により相互に変換が可能である。特に一般式[II]の化合物は空気中の酸素によっても容易に酸化され、一般式[IV]の化合物になることもある。
(工程5)
すなわち、目的とする一般式[II]又は[IV]で表される化合物は一般式[XXI]の化合物を酸化剤で酸化し、メチルスルホキシドとした後、無水酢酸又は無水トリフルオロ酢酸で処理し、プンメラー転位反応を行い、一般式[XXII]で表されるアシルオキシメチルスルフィドとする。その後、これを加水分解することにより製造することができる。
無水酢酸又は無水トリフルオロ酢酸の使用量は一般式[XXI]の化合物1モルに対して1モルから反応溶媒として利用でき、好ましくは1.0〜3.0モルである。
反応時間は反応温度、反応基質、反応量等により異なるが、通常5分〜12時間である。
一般式[II]で表される化合物は一般式[XIX]の化合物を、溶媒中、金属又は有機金属化合物で処理した後、硫黄を反応させることにより製造することができる。
金属の使用量は一般式[XIX]の化合物1モルに対して1〜3モルの範囲から適宜選択すればよく、好ましくは1.0〜1.2モルである。
有機金属化合物の使用量は一般式[XIX]の化合物1モルに対して1〜3モルの範囲から適宜選択すればよく、好ましくは1.0〜1.2モルである。
反応時間は反応温度、反応基質、反応量等により異なるが、通常30分〜12時間である。
一般式[II]で表される化合物は一般式[XI]で表される化合物を前記<製造方法6>と同様に、ジアゾニウム塩とする。その後、キサントゲン酸塩又はチオシアン酸塩と反応させ、アルカリ加水分解することにより製造することができる。
反応時間は反応温度、反応基質、反応量等により異なるが、通常10分〜20時間である。
一般式[II]で表される合成中間体は一般式[XXIII]の化合物をクロロスルホン酸で処理して一般式[XXIV]のスルホニルクロリドとし、これを水素化リチウムアルミニウム、亜鉛と酸、スズと酸もしくは赤りんとヨウ素を用いて還元することにより製造することができる。
クロロスルホン酸の使用量は一般式[XXIII]の化合物1モルに対して2〜10モルの範囲から適宜選択すればよく、好ましくは2.2〜3.5モルである。
水素化リチウムアルミニウム、亜鉛と酸、スズ、酸、赤りん及びヨウ素の使用量は一般式[XXIII]の化合物1モルに対して1〜5モルの範囲から適宜選択すればよく、好ましくは1.5〜2.0モルである。
一般式[IV]で表される化合物は一般式[XXIII]の化合物と二塩化二イオウとを、触媒存在下又は非存在下、反応させることで製造することができる。さらに、一般式[II]で表される化合物は一般式[IV]で表される化合物を常法により還元することで製造することができる。
触媒の使用量は一般式[XXIII]の化合物1モルに対して1〜5モルの範囲から適宜選択すればよく、好ましくは1.1〜2.0モルである。
反応温度は−30℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは−10℃〜100℃の範囲で行うのがよい。
反応時間は反応温度、反応基質、反応量等により異なるが、通常1〜20時間である。
さらに、一般式[IX]の化合物で、B5が電子吸引性基であるときは、置換反応により一般式[II−1]の合成中間体を製造することができる。
すなわち、目的とする一般式[II−1]で表される3−トリアゾリルフェニルチオール誘導体は一般式[IX]の化合物と一般式[XXV]の化合物とを溶媒中、塩基の存在下で反応させた後、鉱酸等にて中和することにより製造することができる。
製造中間体[VI]の合成
一般式[VI]で表される合成中間体は製造方法8と同様にして、一般式[XVI]の化合物を一般式[XVII]の化合物に導き、式[XXVI]の抱水ヒドラジン[XXVI]と反応させることにより製造することができる。
また、一般式[VI]で表される合成中間体は製造法7と同様にして、一般式[XXVII]の化合物と一般式[XV−1]の化合物又は一般式[XV−2]の化合物とを反応させることにより製造することができる。
一般式[VI]で表される合成中間体は一般式[XXVII]で表される化合物とアンモニア水とを反応させることにより一般式[XXVII−2]で表されるアミドラゾンを製造する。さらに、この反応物と一般式[XV−3]で表される化合物又は一般式[XV−4]で表される化合物とを反応させることにより製造することができる。
製造中間体[XIV]の合成
(工程13)
一般式[XXIX]で表される化合物は一般式[XVIII]で表されるフェニルヒドラジン誘導体と一般式[XXVIII]で表される化合物とを溶媒中、塩基の存在下で反応させることによりアシル化する。その後、目的とする一般式[XIV]で表される化合物は一般式[XXIX]で表される化合物をハロゲン化剤で処理することにより製造することができる。
反応時間は反応温度、反応基質、反応量等により異なるが、通常10分〜20時間である。
又は、目的とする一般式[XIV]で表される化合物は一般式[XVIII]で表されるフェニルヒドラジン誘導体と一般式[XXX]で表されるアルデヒド化合物とを、溶媒中、酸触媒の存在下/非存在下、で反応させることにより、一般式[XXXI]で表されるフェニルヒドラゾン誘導体とした後、ハロゲン化剤で処理することにより製造することができる。
一般式[XXXVI]で表される3−チオアニリン誘導体は一般式[XXXII]で表されるアセトアニリドを中間体製造方法1の記載と同様にして、一般式[XXXIV]で表されるジスルフィド又は一般式[XXXV]で表されるチオールとし、さらに、前記製造法1又は製造法2の記載の方法を用いることにより製造することができる。
鉱酸の使用量は、化合物[XXXVI]1モルに対して2〜10モルの範囲から適宜選択すればよく、好ましくは3〜5モルである。
反応時間は反応温度、反応基質、反応量等により異なるが、通常30分〜5時間である。
二塩化オキザリル又はホスゲンの使用量は一般式[I−3]で表される化合物1モルに対して、1モルから反応溶媒量と同等量の範囲から適宜選択すればよく、好ましくは1.1から3モルである。
[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−クロロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド(化合物番号7)の製造
(1)5−アセチルチオ−2−クロロ−4−メチルアセトアニリドの合成
クロロスルホン酸100mlに2−クロロ−4−メチルアセトアニリド55gを、5〜10℃で加えた。この混合液に60%発煙硫酸65gを10〜15℃で加え、室温で1時間攪拌後、さらに90℃で18時間攪拌した。室温冷却後、反応混合物を氷水に注加し、トルエンを加え、不溶物をロ別後、有機層を水洗し、無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、得られた残渣と、赤リン31g、ヨウ素1g及び酢酸200mlの混合物を1時間加熱還流し、反応液を室温へ冷却した。不溶物をロ別後、減圧下濃縮し、水を加え、酢酸エチルで抽出した。有機層を水で洗浄し、無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去し、残査をシリカゲルカラムクロマトグラフィーで精製して、5−アセチルチオ−2−クロロ−4−メチルアセトアニリド14gを得た。
5−アセチルチオ−2−クロロ−4−メチルアセトアニリド14gをエタノール150mlに溶解し、50%水酸化ナトリウム水溶液22gを加え、4時間加熱還流した。得られた反応混合物を、減圧下濃縮し、水を加え、希塩酸で中和後、酢酸エチルで抽出した。有機層を水で洗浄し、無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去して、2−クロロ−4−メチル−5−メルカプトアニリン9.4gを得た。
2−クロロ−4−メチル−5−メルカプトアニリン9.4g、ヨウ化2,2,2−トリフルオロエチル20g、炭酸カリウム13g、N,N−ジメチルホルムアミド200mlの混合物を室温で16時間攪拌した。反応混合物を減圧下濃縮し、水を加え、トルエン抽出した。有機層を水で洗浄し、無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去して2−クロロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)アニリン13.5gを得た。
1H−NMRデータ(CDCl3/TMS δ(ppm)値):2.32(3H,s),3.33(2H,q),3.96(2H,s),6.94(1H,s),7.11(1H,s)
濃塩酸30ml中に、2−クロロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)アニリン13.5gを室温で滴下し、この混合物に、亜硝酸ナトリウム3.8gを含む水溶液を、0〜5℃で滴下し、そのまま1時間攪拌してジアゾニウム塩を調製した。塩化スズ・2水和物36gを6N塩酸250mlに溶解し、この混合溶液に前記のジアゾニウム塩水溶液を、0〜5℃で滴下し、さらに室温で、2時間攪拌した。トルエンを加え、水酸化ナトリウム水溶液で中和し、不溶物をロ別後、有機層を水洗し、無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去して、2−クロロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニルヒドラジン12.1gを得た。
2−クロロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニルヒドラジン4.1g、トリフルオロアセトアルデヒドエチルヘミアセタール2.3g、p−トルエンスルホン酸一水和物0.1g、エタノール50mlの混合物を、6時間加熱還流した。得られた反応混合物を減圧下濃縮し、水を加え、トルエンで抽出した。有機層を水洗し、無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去し、トリフルオロアセトアルデヒド {2−クロロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル}ヒドラゾン3.6gを得た。
トリフルオロアセトアルデヒド {2−クロロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル}ヒドラゾン3.6g(10.3ミリモル)をN,N−ジメチルホルムアミド30mlに溶解し、室温下、N−ブロモスクシイミド2.0gを加え、室温で2時間攪拌した。反応混合物を水に注加し、トルエンで抽出し、有機層を水洗後、無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去して、N−{2−クロロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル}トリフルオロアセトヒドラゾノイルブロミド4.1gを得た。
N−{2−クロロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル}トリフルオロアセトヒドラゾノイルブロミド4.1g、S−メチルイソチオ尿素ヨウ化水素塩4.4g、テトラヒドロフラン100mlの混合物に、室温下、トリエチルアミン3.5gを加え、さらに、50℃で3時間攪拌した。反応混合物を減圧下濃縮し、得られた残渣にキシレンを加え、2時間加熱還流した。反応混合物を室温へ冷却した後、水洗し、有機層を無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、得られた粗結晶をエタノールから再結晶して、淡灰色結晶(融点193〜194℃)の[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−クロロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド2.0gを得た。
[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−クロロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルホキシド(本発明化合物番号8)の製造
[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−クロロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド1.3gを酢酸エチル80mlに溶解し、氷冷下、m−クロロ過安息香酸0.9g(純度75%)を加えた。氷冷下、2時間攪拌後、チオ硫酸ナトリウム水溶液で洗浄し、次いで炭酸水素ナトリウム水溶液で洗浄した後、無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、得られた結晶を四塩化炭素で洗浄して、白色結晶(融点235〜237℃)の[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−クロロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルホキシド1.2gを得た。
[5−(3−ニトロ−1,2,4−トリアゾリル)−2−ジフルオロメチルフェニル]2,2,2−トリフルオロエチルスルフィド(化合物番号11)の製造
(1)4−(3−ニトロ−1,2,4−トリアゾリル)−2−フルオロベンズアルデヒドの合成
水素化ナトリウム1.2g(60%)及びN,N−ジメチルホルムアミド50mlの懸濁液に、氷冷下、3−ニトロ−1,2,4−トリアゾール3.4gのN,N−ジメチルホルムアミド溶液10mlを滴下した。水素の発生が止まった後、2,4−ジフルオロベンズアルデヒド4.3gを加え、70℃で3時間撹拌した。減圧下濃縮し、水200mlを加え、酢酸エチルで抽出し、酢酸エチル層を水洗後、無水硫酸マグネシウムで乾燥した。溶媒を減圧下で留去して得られた粗結晶をジイソプロピルエーテルで洗浄して、4−(3−ニトロ−1,2,4−トリアゾリル)−2−フルオロベンズアルデヒド1.6gを得た。
4−(3−ニトロ−1,2,4−トリアゾリル)−2−フルオロベンズアルデヒド1.6g、炭酸カリウム1.3gとN,N−ジメチルホルムアミド50mlの混合物に、氷冷下、2,2,2−トリフルオロエチルメルカプタン0.8gを滴下し、0〜10℃で4時間撹拌した。減圧下濃縮し、水200mlを加え、酢酸エチルで抽出し、有機層を水洗後、無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、4−(3−ニトロ−1,2,4−トリアゾリル)−2−(2,2,2−トリフルオロエチルチオ)ベンズアルデヒド1.8gを得た。
4−(3−ニトロ−1,2,4−トリアゾリル)−2−(2,2,2−トリフルオロエチルチオ)ベンズアルデヒド1.8g、塩化メチレン20mlの混合物に、氷冷下、ジエチルアミノサルファートリフルオリド2.6gを加え、さらに6時間加熱還流した。室温冷却後、氷水に注加し、有機相を炭酸水素ナトリウム水溶液及び水で洗浄後、無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、残査をシリカゲルカラムクロマトグラフィーで精製し、淡黄色結晶(融点74〜76℃)の[5−(3−ニトロ−1,2,4−トリアゾリル)−2−ジフルオロメチルフェニル]−2,2,2−トリフルオロエチルスルフィドを得た。
[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド(化合物番号1)の製造
(1)5−アセチルチオ−2−フルオロ−4−メチルアセトアニリドの合成
クロロスルホン酸500gに、2−フルオロ−4−メチルアセトアニリド150gを、50℃以下で加え、さらに1時間攪拌した。反応混合物を氷水−酢酸エチルの混合物に注加し、有機層を水洗し、無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去し、固体の残渣を得た。得られた固体の残渣を酢酸350mlに溶解し、この溶液を、赤リン84g、ヨウ素1g及び酢酸300mlの混合物に、加熱還流下、1時間かけて滴下し、2時間加熱還流した。室温冷却後、不溶物をロ別後、減圧下濃縮し、水を注加し、酢酸エチルで抽出した。有機層を水洗し、無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去し、5−アセチルチオ−2−フルオロ−4−メチルアセトアニリド211gを得た。
5−アセチルチオ−2−フルオロ−4−メチルアセトアニリド211gをエタノール500mlに溶解し、この溶液に、水酸化カリウム200g/水500mlの溶液を30分かけて滴下し、5時間加熱還流した。室温冷却後、希塩酸で中和し、減圧下濃縮し、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去して2−フルオロ−4−メチル−5−メルカプトアニリン129gを得た。
2−フルオロ−4−メチル−5−メルカプトアニリン129gのN,N−ジメチルホルムアミド1000ml溶液に、ヨウ化2,2,2−トリフルオロエチル250g、炭酸カリウム125gを加え、さらにロンガリット10gを添加し、室温で8時間撹拌した。反応液を水に注加し、酢酸エチルで抽出し、無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去して、2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)アニリン182gを得た。
1H−NMRデータ(CDCl3/TMS δ(ppm)値):2.36(3H,s),3.30(2H,q),3.64(2H,s),6.86(1H,d),6.98(1H,d)
濃硫酸300mlに亜硝酸ナトリウム53gを50℃以下で加え、さらに酢酸300mlを50℃以下で滴下した。この混合溶液に20℃以下で、2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)アニリン182gの酢酸100ml溶液を2時間かけて滴下し、20℃で3時間撹拌した。この反応混合物を、塩化スズ(II)2水和物390gと6N塩酸1000mlの混合溶液に5℃以下で滴下し、30分攪拌した。この反応混合物にトルエンを加え、10%水酸化ナトリウム水溶液で中和した。不溶物をロ別後、有機層を無水硫酸マグネシウムで乾燥し、減圧下で濃縮して、2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニルヒドラジン177gを得た。
2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニルヒドラジン3.1g、トリフルオロアセトアルデヒドエチルヘミアセタール1.9g、メタンスルホン酸0.5g及びエタノール100mlの混合物を5時間加熱還流した。室温冷却後、減圧下濃縮し、酢酸エチルで抽出し、有機層を無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、トリフルオロアセトアルデヒド {2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル}ヒドラゾン3.7gを得た。
トリフルオロアセトアルデヒド {2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル}ヒドラゾン3.7gをN,N−ジメチルホルムアミド50mlに溶解し、室温下、N−ブロモスクシイミド2.0gを加え、室温で30分攪拌した。反応混合物を水に注加し、酢酸エチルで抽出し、有機層を無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、N−{2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル}トリフルオロアセトヒドラゾノイルブロミド4.4gを得た。
テトラヒドロフラン100mlにS−メチルイソチオ尿素ヨウ化水素塩4.5g、N−{2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル}トリフルオロアセトヒドラゾノイルブロミド4.4g、トリエチルアミン3.5gを加え、8時間加熱還流した。室温冷却後、減圧下濃縮し、酢酸エチルで抽出し、有機層を水洗後、無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、得られた個体をカラムクロマトグラフィー(展開溶媒 酢酸エチル:ヘキサン=4:1)で精製し、淡黄色結晶(融点171〜173℃)の[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド2.9gを得た。
[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルホキシド(本発明化合物番号2)の製造
[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド1.9gをクロロホルム100mlに溶解し、0℃で、m−クロロ過安息香酸1.0gを加え、さらに1時間室温で攪拌した。溶媒を減圧留去し、得られた残渣をカラムクロマトグラフィー(展開溶媒 酢酸エチル:ヘキサン:トリエチルアミン=50:50:1)で精製し、淡黄色結晶(融点236〜238℃)の[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルホキシド1.8gを得た。
[5−(5−トリフルオロアセチルアミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド(化合物番号5)の製造
[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド1.1gをトリフルオロ酢酸無水物50mlに加え、室温で12時間攪拌した。溶媒を減圧下留去し、得られた個体をカラムクロマトグラフィー(展開溶媒、酢酸エチル:ヘキサン=2:1)で精製し、淡黄色結晶(融点122〜125℃)の[5−(5−トリフルオロアセチルアミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド1.1gを得た。
[5−(5−アミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルホキシド(本発明化合物番号6)の製造
[5−(5−トリフルオロアセチルアミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルフィド0.8gをクロロホルム50mlに溶解し、0℃で、m−クロロ過安息香酸0.3gを加え、室温で1時間攪拌した。溶媒を減圧下留去し、得られた個体をカラムクロマトグラフィー(展開溶媒、酢酸エチル:ヘキサン=1:1)で精製し、淡黄色粉末(融点233〜237℃)の[5−(5−トリフルオロアセチルアミノ−3−トリフルオロメチル−1,2,4−トリアゾリル)−4−フルオロ−2−メチルフェニル]2,2,2−トリフルオロエチルスルホキシド0.6gを得た。
尚、化合物番号は以後の記載において参照される。
化合物番号49:2.56(3H,s),3.40(2H,q),5.29(2H,s),7.21(1H,d),7,67(1H,d)
化合物番号59:1.22-1.28(3H,m), 2.55(3H,s), 3.40(2H,q),3.46-3.55(2H,m),4.12(1H,t),7.20(1H,d),7.63(1H,d)
化合物番号101:2.54(3H,s), 3.07(3H,d), 3.3.9(2H,q),4.25(1H,s),7.17(1H,d),7.61(1H,d)
化合物番号128:1.32(6H,t),2.50(3H,s),3.25(4H,q),3.44(2H,q),7.19(1H,s),7.75(1H,s)
化合物番号158:1.98(3H,s), 2.56(3H,s), 3.05(3H,s),3.36(2H,q),3.85(2H,q),7.16(1H,d),7.61(1H,d)
化合物番号184:2.29(1H,d), 2.53(3H,s), 3.39(2H,q),3.82(2H,q),4.20(2H,dd),4.34(1H,s),7.16(1H,d),7.61(1H,d)
化合物番号185:2,29(1H,t), 2.47(3H,s), 3.42-3.57(2H,m),3.83(2H,q),4.22(2H,d),
4.40(1H,s), 7.22(1H,s), 8.12(1H,s)
化合物番号193:2.30(1H,t), 2.55(3H,s), 3.40(2H,q),4.24(2H,q),4.40(1H,s),7.20(1H,d),7.63(1H,d)
化合物番号195:1.22-1.39(1H,m), 1.48-1.57(1H,m),2.06-2.14(1H,m),2.52(3H,s),
3.07(1H,dd), 3.29(1H,dd), 3.42,(2H,t), 4.75(2H,s), 7.16(1H,d), 7.65(1H,d)
化合物番号209:2.61(3H,s),3.42(2H,q),7.31(1H,d),7.74(1H,d)
<中間体製造例1>
(1)5−アセチルチオ−2,4−ジメチルアセトアニリドの合成
2−フルオロ−4−メチルアセトアニリド78gをクロロスルホン酸168gに40℃以下で加え、さらに70℃で2時間撹拌した。反応混合物を氷水−酢酸エチルに注加し、有機層を水洗し、無水硫酸マグネシウムで乾燥後、溶媒を減圧下留去し、固体の残渣を得た。得られた固体の残渣を酢酸200mlに溶解し、この溶液を、赤リン72g、ヨウ素1g及び酢酸300mlの混合溶液に、加熱還流下、1時間で滴下し、さらに4時間加熱還流した。不溶物をロ別後、減圧下で酢酸を留去し、水を加え、残渣を酢酸エチルにて抽出し、水洗後、無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、5−アセチルチオ−2,4−ジメチルアセトアニリド42gを得た。
5−アセチルチオ−2−フルオロ−4−メチルアセトアニリド42gを5%水酸化カリウム水溶液に加え、18時間加熱還流した。室温冷却後、希塩酸でpH7に調整し、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥し、溶媒を減圧下留去して2,4−ジメチル−5−メルカプトアニリン25gを得た。
2,4−ジメチル−5−メルカプトアニリン20g及びN,N−ジメチルホルムアミド150mlの混合溶液に、ヨウ化2,2,2−トリフルオロエチル41g、炭酸カリウム24gを添加し、さらにロンガリット4gを加え、24時間室温で撹拌した。反応混合物を水に注加し、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥し、溶媒を減圧下留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;ヘキサン:酢酸エチル=5:1)にて精製して、2,4−ジメチル−5−(2,2,2−トリフルオロエチルチオ)アニリン29gを得た。
1H−NMRデータ(CDCl3/TMS δ(ppm)値)
2.13(3H,s),3.34(3H,s),3.32(2H,q),3.52(2H,s),6.84(1H,s),6.91(1H,s)
化合物番号6(30部)、シクロヘキサノン(20部)、ポリオキシエチレンアルキルアリールエーテル(11部)、アルキルベンゼンスルホン酸カルシウム(4部)及びメチルナフタリン(35部)を均一に溶解して乳剤とした。
化合物番号2(10部)、ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩(0.5部)、ポリオキシエチレンアルキルアリールエーテル(0.5部)、珪藻土(24部)及びクレー(65部)を均一に混合粉砕して水和剤とした。
化合物番号6(2部)、珪藻土(5部)及びクレー(93部)を均一に混合粉砕して粉剤とした。
化合物番号2(5部)、ラウリルアルコール硫酸エステルのナトリウム塩(2部)、リグニンスルホン酸ナトリウム(5部)、カルボキシメチルセルロース(2部)及びクレー(86部)を均一に混合粉砕した。この混合物(100部)に水(20部)を加えて練合し、押出式造粒機を用いて14〜32メッシュの粒状に加工したのち、乾燥して粒剤とした。
製剤例2に準じて調製した水和剤を有効成分として500ppmの濃度に水で希釈した。その薬液に、予めナミハダニ成虫を接種しておいたダイズ苗を浸漬し、風乾した。処理後のダイズ苗は25℃の恒温室に置き、13日後に生存虫数を調査し、数2の計算式により防除価を求めた。試験は1連制にて行った。この試験における結果を表11及び表12に示す。
製剤例2に準じて調製した水和剤を有効成分として100ppmの濃度に水で希釈した。その薬液に、予めナミハダニ成虫を接種しておいたダイズ苗カップの土壌100gに5ml潅注した。処理後のダイズ苗は25℃の恒温室に置き、13日後に生存虫数を調査し、数2の計算式により防除価を求めた。この試験における結果を表13及び表14に示す。
製剤例2に準じて調製した水和剤を有効成分として500ppmの濃度に水で希釈した。その薬液に、イネ芽だし籾を浸漬し、容量60mlのプラスティックカップに入れた。これにトビイロウンカ4齢幼虫を10頭放ち、蓋をして25℃の恒温室に置いた。6日後に生存虫数を数え、数1の計算式により死虫率を求めた。試験は1連制にて行った。この試験における結果を表15及び表16に示す。
サツマイモネコブセンチュウ制線虫試験
表1〜表6に記載された化合物(5部)及び展着剤としてTween20(ポリオキシエチレンソルビタンモノラウレートの商品名)(1部)をN,N−ジメチルホルムアミド(94部)に溶解し、表1〜表6に記載された化合物の5%乳剤を製造した。この乳剤に蒸留水を加え、表1〜表6に記載された化合物の濃度が20ppmとなるように希釈溶液を調整した。この希釈溶液0.5mlと、サツマイモネコブセンチュウ第二期幼虫100頭を含む水の懸濁液0.5mlとを混合し、25℃の恒温室に置いた。5日後に生存線虫数を数え、数3の計算式により制線虫活性を求めた。試験は2連制にて行った。この試験における結果を表17及び表18に示す。
なお、2004年10月20日に出願された日本特許出願2004−305251号の明細書、特許請求の範囲、図面及び要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。
Claims (7)
- 一般式[I]で表される3−トリアゾリルフェニルスルフィド誘導体:
nは1であり、
A1 は、C 1 〜C 6 アルキル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)、C 1 〜C 6 アルキルチオ基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)、又はC 1 〜C 6 アルキルスルフィニル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)であり、
A3 は、−NR 2 R 3 基、又は−N(COR 2 )R 3 基であり、R 2 及びR 3 は、互いに独立して、水素原子、又はC 1 〜C 6 アルキル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)であり、
B2 はハロゲン原子であり、
B4 はC 1 〜C6アルキル基である。 - Rがトリフルオロエチル基であり、
nが1であり、
A1がC1〜C6アルキル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)、C1〜C6アルキルチオ基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)、又はC1〜C6アルキルスルフィニル基(該基はハロゲン原子によりモノ置換又はポリ置換されてもよい)であり、
A3がアミノ基であり、
B2 がハロゲン原子であり、
B4 がC 1 〜C 6 アルキル基である
請求項1に記載の3−トリアゾリルフェニルスルフィド誘導体。 - A1がトリフルオロメチル基であり、
A3がメチルアミノ基、トリフルオロアセチルアミノ基である
請求項1に記載の3−トリアゾリルフェニルスルフィド誘導体。 - A1がトリフルオロメチル基、トリフルオロメチルチオ基、又は2,2,2−トリフルオロエチルスルフィニル基であり、
A3がアミノ基である請求項2に記載の3−トリアゾリルフェニルスルフィド誘導体。 - B4がメチル基である請求項5に記載のアニリン誘導体。
- 請求項1乃至4のいずれかに記載の3−トリアゾリルフェニルスルフィド誘導体を有効成分として含有することを特徴とする農園芸用殺虫・殺ダニ剤・殺線虫剤。
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Families Citing this family (548)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007308392A (ja) * | 2006-05-16 | 2007-11-29 | Bayer Cropscience Ag | 殺虫性ベンズアミジン類 |
US8741803B2 (en) | 2007-08-10 | 2014-06-03 | Kumiai Chemical Industry Co., Ltd. | Pesticidal composition and method for controlling pest |
JP5295971B2 (ja) | 2007-10-18 | 2013-09-18 | クミアイ化学工業株式会社 | 3−アルコキシ−1−フェニルピラゾ−ル誘導体及び有害生物防除剤 |
KR101574655B1 (ko) | 2007-11-30 | 2015-12-04 | 이하라케미칼 고교가부시키가이샤 | (1h-1,2,4-트리아졸-1-일)아릴 화합물 및 그 제조방법 |
WO2009069311A1 (ja) | 2007-11-30 | 2009-06-04 | Ihara Chemical Industry Co., Ltd. | 3-メルカプトアニリン化合物の製造法 |
EP2274982A1 (de) * | 2009-07-16 | 2011-01-19 | Bayer CropScience AG | Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut |
WO2011006603A2 (de) * | 2009-07-16 | 2011-01-20 | Bayer Cropscience Ag | Synergistische wirkstoffkombinationen mit phenyltriazolen |
CN102471290B (zh) * | 2009-07-16 | 2016-02-03 | 拜耳知识产权有限责任公司 | 手性3-三唑基亚砜衍生物的制备方法 |
JP2011042643A (ja) | 2009-07-24 | 2011-03-03 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
WO2011020579A1 (de) | 2009-08-20 | 2011-02-24 | Bayer Cropscience Ag | Verfahren zur herstellung von 1-phenyl-1,2,4-triazolen |
CN102471291B (zh) * | 2009-08-20 | 2015-04-22 | 拜尔农作物科学股份公司 | 用作杀螨剂和杀昆虫剂的3-三唑基苯基取代的硫化物衍生物 |
WO2011029506A1 (de) | 2009-08-20 | 2011-03-17 | Bayer Cropscience Ag | 3-[1-(3-haloalkyl)-triazolyl]-phenyl-sulfid-derivate als akarizide und insektizide |
ES2533798T3 (es) | 2009-10-12 | 2015-04-14 | Bayer Cropscience Ag | 1-(pirid-3-il)-pirazol y 1-(pirimid-5-il)- pirazol como agentes para combatir parásitos |
BR112012006239A2 (pt) * | 2009-10-12 | 2015-09-08 | Bayer Cropscience Ag | amidas e tioamidas enquanto agentes pesticidas |
UY32940A (es) | 2009-10-27 | 2011-05-31 | Bayer Cropscience Ag | Amidas sustituidas con halogenoalquilo como insecticidas y acaricidas |
JP2011093855A (ja) | 2009-10-30 | 2011-05-12 | Bayer Cropscience Ag | 殺虫性オキサゾリジノン誘導体 |
WO2011080044A2 (en) | 2009-12-16 | 2011-07-07 | Bayer Cropscience Ag | Active compound combinations |
JP2011136928A (ja) | 2009-12-28 | 2011-07-14 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
WO2011098443A1 (de) | 2010-02-10 | 2011-08-18 | Bayer Cropscience Ag | Spiroheterocyclisch-substituierte tetramsäure-derivate |
WO2011098440A2 (de) | 2010-02-10 | 2011-08-18 | Bayer Cropscience Ag | Biphenylsubstituierte cyclische ketoenole |
ES2523503T3 (es) | 2010-03-04 | 2014-11-26 | Bayer Intellectual Property Gmbh | 2-Amidobencimidazoles sustituidos con fluoroalquilo y su uso para el aumento de la tolerancia al estrés en plantas |
EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
JP5868957B2 (ja) | 2010-05-05 | 2016-02-24 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 殺虫剤としてのチアゾール誘導体 |
BR112012030399A2 (pt) | 2010-06-01 | 2020-10-20 | Kumiai Chemical Industry Co., Ltd. | composto de triazol com atividades pesticidas |
KR20130088127A (ko) | 2010-06-15 | 2013-08-07 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 신규 오르토-치환된 아릴 아미드 유도체 |
CN103068235B (zh) | 2010-06-18 | 2016-04-20 | 拜耳知识产权有限责任公司 | 具有杀虫和杀螨特性的活性成分结合物 |
AR083431A1 (es) | 2010-06-28 | 2013-02-27 | Bayer Cropscience Ag | Compuestos heterociclicos como pesticidas |
JP2013529660A (ja) | 2010-06-29 | 2013-07-22 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 環状カルボニルアミジン類を含む改善された殺虫剤組成物 |
WO2012001068A2 (de) | 2010-07-02 | 2012-01-05 | Bayer Cropscience Ag | Insektizide oder akarizide formulierungen mit verbesserter verfügbarkeit auf pflanzenoberflächen |
WO2012004293A2 (de) | 2010-07-08 | 2012-01-12 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
JP2012017289A (ja) | 2010-07-08 | 2012-01-26 | Bayer Cropscience Ag | 殺虫性ピロリン誘導体 |
MX2013000298A (es) | 2010-07-09 | 2013-02-27 | Bayer Ip Gmbh | Derivados de antranilamida como pesticidas. |
ES2603032T3 (es) | 2010-07-15 | 2017-02-23 | Bayer Intellectual Property Gmbh | Compuestos de 3-piridil-heteroarilcarboxamida como pesticidas |
WO2012028583A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Cropscience Ag | Deltamethrin enthaltende formulierungen |
JP2012082186A (ja) | 2010-09-15 | 2012-04-26 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
JP2012062267A (ja) | 2010-09-15 | 2012-03-29 | Bayer Cropscience Ag | 殺虫性ピロリンn−オキサイド誘導体 |
WO2012045680A2 (de) | 2010-10-04 | 2012-04-12 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
JP2013541554A (ja) | 2010-10-21 | 2013-11-14 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | N−ベンジルヘテロ環式カルボキサミド類 |
EP2630133A1 (de) | 2010-10-22 | 2013-08-28 | Bayer Intellectual Property GmbH | Neue heterocylische verbindungen als schädlingsbekämpfungsmittel |
EP2446742A1 (de) | 2010-10-28 | 2012-05-02 | Bayer CropScience AG | Insektizide oder akarizide Zusammensetzungen enthaltend Mono- oder Disacchariden als Wirkungsverstärker |
UA109460C2 (uk) | 2010-11-02 | 2015-08-25 | Байєр Інтелекчуал Проперті Гмбх | N-гетарилметилпіразолілкарбоксаміди |
CN103313971B (zh) | 2010-11-15 | 2015-12-02 | 拜耳知识产权有限责任公司 | N-芳基吡唑(硫代)甲酰胺 |
EP2646413A1 (de) | 2010-11-29 | 2013-10-09 | Bayer Intellectual Property GmbH | Alpha-beta-ungesättigte imine |
EP2645856A1 (en) | 2010-12-01 | 2013-10-09 | Bayer Intellectual Property GmbH | Use of fluopyram for controlling nematodes in crops and for increasing yield |
US20130317067A1 (en) | 2010-12-09 | 2013-11-28 | Bayer Intellectual Property Gmbh | Pesticidal mixtures with improved properties |
WO2012076471A1 (en) | 2010-12-09 | 2012-06-14 | Bayer Cropscience Ag | Insecticidal mixtures with improved properties |
TWI667347B (zh) | 2010-12-15 | 2019-08-01 | 瑞士商先正達合夥公司 | 大豆品種syht0h2及偵測其之組合物及方法 |
DE102010063691A1 (de) | 2010-12-21 | 2012-06-21 | Bayer Animal Health Gmbh | Ektoparasitizide Wirkstoffkombinationen |
EP2471363A1 (de) | 2010-12-30 | 2012-07-04 | Bayer CropScience AG | Verwendung von Aryl-, Heteroaryl- und Benzylsulfonamidocarbonsäuren, -carbonsäureestern, -carbonsäureamiden und -carbonitrilen oder deren Salze zur Steigerung der Stresstoleranz in Pflanzen |
CN103476256B (zh) | 2011-02-17 | 2016-01-20 | 拜耳知识产权有限责任公司 | Sdhi杀真菌剂用于常规育种的asr耐受性的茎溃疡抗性和/或蛙眼叶斑病抗性大豆品种的用途 |
US9510594B2 (en) | 2011-02-17 | 2016-12-06 | Bayer Intellectual Property Gmbh | Use of SDHI fungicides on conventionally bred ASR-tolerant, stem canker resistant and/or frog-eye leaf spot resistant soybean varieties |
CN103492367B (zh) | 2011-02-17 | 2015-04-01 | 拜耳知识产权有限责任公司 | 用于治疗的取代的3-(联苯-3-基)-8,8-二氟-4-羟基-1-氮杂螺[4.5]癸-3-烯-2-酮 |
ES2550391T3 (es) | 2011-03-01 | 2015-11-06 | Bayer Intellectual Property Gmbh | 2-Aciloxi-pirrolin-4-onas |
AR085509A1 (es) | 2011-03-09 | 2013-10-09 | Bayer Cropscience Ag | Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas |
WO2012120105A1 (en) | 2011-03-10 | 2012-09-13 | Bayer Cropscience Ag | Use of lipochito-oligosaccharide compounds for safeguarding seed safety of treated seeds |
MX350121B (es) | 2011-03-18 | 2017-08-28 | Bayer Ip Gmbh | Derivados de n-(3-carbamoilfenil)-1h-pirazol-5-carboxamida y el uso de los mismos para el control de plagas de animales. |
AR085872A1 (es) | 2011-04-08 | 2013-10-30 | Basf Se | Derivados heterobiciclicos n-sustituidos utiles para combatir parasitos en plantas y/o animales, composiciones que los contienen y metodos para combatir dichas plagas |
AR085585A1 (es) | 2011-04-15 | 2013-10-09 | Bayer Cropscience Ag | Vinil- y alquinilciclohexanoles sustituidos como principios activos contra estres abiotico de plantas |
AR090010A1 (es) | 2011-04-15 | 2014-10-15 | Bayer Cropscience Ag | 5-(ciclohex-2-en-1-il)-penta-2,4-dienos y 5-(ciclohex-2-en-1-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas, usos y metodos de tratamiento |
AR085568A1 (es) | 2011-04-15 | 2013-10-09 | Bayer Cropscience Ag | 5-(biciclo[4.1.0]hept-3-en-2-il)-penta-2,4-dienos y 5-(biciclo[4.1.0]hept-3-en-2-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas |
EP2535334A1 (de) | 2011-06-17 | 2012-12-19 | Bayer CropScience AG | Kristalline Modifikationen von Penflufen |
EP2540163A1 (en) | 2011-06-30 | 2013-01-02 | Bayer CropScience AG | Nematocide N-cyclopropyl-sulfonylamide derivatives |
JP2014520776A (ja) | 2011-07-04 | 2014-08-25 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 植物における非生物的ストレスに対する活性薬剤としての置換されているイソキノリノン類、イソキノリンジオン類、イソキノリントリオン類およびジヒドロイソキノリノン類または各場合でのそれらの塩の使用 |
US20140296064A1 (en) | 2011-07-15 | 2014-10-02 | Basf Se | Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests i |
WO2013014126A1 (de) | 2011-07-26 | 2013-01-31 | Bayer Intellectual Property Gmbh | Veretherte laktatester, verfahren zu ihrer herstellung und ihre verwendung zur verbesserung der wirkung von pflanzenschutzmitteln |
EP2736333A1 (en) | 2011-07-27 | 2014-06-04 | Bayer Intellectual Property GmbH | Seed dressing for controlling phytopathogenic fungi |
EA201400213A1 (ru) | 2011-08-12 | 2014-08-29 | Басф Се | Соединения анилинового типа |
EP2561759A1 (en) | 2011-08-26 | 2013-02-27 | Bayer Cropscience AG | Fluoroalkyl-substituted 2-amidobenzimidazoles and their effect on plant growth |
AR087874A1 (es) | 2011-09-16 | 2014-04-23 | Bayer Ip Gmbh | Uso de acilsulfonamidas para mejorar el rendimiento de las plantas |
US20140302991A1 (en) | 2011-09-16 | 2014-10-09 | Bayer Intellectual Property Gmbh | Use of phenylpyrazolin-3-carboxylates for improving plant yield |
CN107897194A (zh) | 2011-09-16 | 2018-04-13 | 拜耳知识产权有限责任公司 | 5‑苯基‑或5‑苄基‑2‑异噁唑啉‑3‑甲酸酯用于改善植物产量的用途 |
JP2013082632A (ja) | 2011-10-05 | 2013-05-09 | Bayer Cropscience Ag | 農薬製剤及びその製造方法 |
WO2013079601A1 (en) | 2011-12-02 | 2013-06-06 | Basf Se | Method and system for monitoring crops and/or infestation of crops with harmful organismus during storage |
WO2013079600A1 (en) | 2011-12-02 | 2013-06-06 | Basf Se | Method and system for monitoring crops during storage |
EP2604118A1 (en) * | 2011-12-15 | 2013-06-19 | Bayer CropScience AG | Active ingredient combinations having insecticidal and acaricidal properties |
WO2013092519A1 (en) | 2011-12-19 | 2013-06-27 | Bayer Cropscience Ag | Use of anthranilic acid diamide derivatives for pest control in transgenic crops |
US9204645B2 (en) | 2011-12-20 | 2015-12-08 | Bayer Intellectual Property Gmbh | Insecticidal aromatic amides |
WO2013092868A1 (en) | 2011-12-21 | 2013-06-27 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
EP2606726A1 (de) * | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | N-Arylamidine-substituierte trifluoroethylsulfid-Derivate als Akarizide und Insektizide |
WO2013092943A1 (en) | 2011-12-23 | 2013-06-27 | Basf Se | Isothiazoline compounds for combating invertebrate pests |
RU2628290C2 (ru) | 2012-01-21 | 2017-08-15 | Байер Интеллектчуал Проперти Гмбх | Применение стимуляторов иммунной защиты для борьбы с вредными бактериальными организмами на культурных растениях |
WO2013113789A1 (en) | 2012-02-02 | 2013-08-08 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
JP2015515454A (ja) | 2012-03-14 | 2015-05-28 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 殺有害生物性アリールピロリジン類 |
WO2013144228A1 (en) | 2012-03-29 | 2013-10-03 | Basf Se | Pesticidal methods using heterocyclic compounds and derivatives for combating animal pests |
US9334238B2 (en) | 2012-03-30 | 2016-05-10 | Basf Se | N-substituted pyridinylidenes for combating animal pests |
WO2013144223A1 (en) | 2012-03-30 | 2013-10-03 | Basf Se | N-substituted pyrimidinylidene compounds and derivatives for combating animal pests |
US20150065343A1 (en) | 2012-04-02 | 2015-03-05 | Basf Se | Acrylamide compounds for combating invertebrate pests |
MX2014011995A (es) | 2012-04-03 | 2015-09-04 | Basf Se | Compuestos de furanona heterobicíclicos n-sustituidos y derivados para combatir plagas de animales. |
WO2013150115A1 (en) | 2012-04-05 | 2013-10-10 | Basf Se | N- substituted hetero - bicyclic compounds and derivatives for combating animal pests |
EP2649879A1 (en) | 2012-04-10 | 2013-10-16 | Basf Se | Pesticidal mixtures containing fluxapyroxad |
WO2013156331A1 (en) | 2012-04-16 | 2013-10-24 | Basf Se | Synergistic compositions comprising pyraclostrobin and an insecticidal compound |
CN104271567A (zh) | 2012-05-04 | 2015-01-07 | 巴斯夫欧洲公司 | 含取代吡唑的化合物及其作为农药的用途 |
WO2013167633A1 (en) | 2012-05-09 | 2013-11-14 | Basf Se | Acrylamide compounds for combating invertebrate pests |
JP6165847B2 (ja) | 2012-05-16 | 2017-07-19 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺虫性の油中水(w/o)型製剤 |
BR112014028367A2 (pt) | 2012-05-16 | 2017-07-18 | Bayer Cropscience Ag | formulação inseticida de óleo-em-água (o/w). |
AR091104A1 (es) | 2012-05-22 | 2015-01-14 | Bayer Cropscience Ag | Combinaciones de compuestos activos que comprenden un derivado lipo-quitooligosacarido y un compuesto nematicida, insecticida o fungicida |
JP6242872B2 (ja) | 2012-05-24 | 2017-12-06 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | N−チオ−アントラニルアミド化合物、及び殺有害生物剤としてのそれらの使用 |
BR112014029758A2 (pt) | 2012-05-30 | 2017-06-27 | Clariant Finance Bvi Ltd | composição contendo n-metil-n-acilglucamina |
US10813862B2 (en) | 2012-05-30 | 2020-10-27 | Clariant International Ltd. | Use of N-methyl-N-acylglucamines as solubilizers |
EP2854535A1 (en) | 2012-05-30 | 2015-04-08 | Bayer Cropscience AG | Compositions comprising a biological control agent and an insecticide |
EP2863738A2 (en) | 2012-06-14 | 2015-04-29 | Basf Se | Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests |
WO2014005982A1 (de) | 2012-07-05 | 2014-01-09 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
CN104602520A (zh) | 2012-07-31 | 2015-05-06 | 拜尔农作物科学股份公司 | 包括杀虫萜烯混合物和杀虫剂的组合物 |
WO2014026984A1 (de) | 2012-08-17 | 2014-02-20 | Bayer Cropscience Ag | Azaindolcarbonsäure- und -thiocarbonsäureamide als insektizide und akarizide |
AU2013311826A1 (en) | 2012-09-05 | 2015-03-26 | Bayer Cropscience Ag | Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress |
AR093771A1 (es) | 2012-10-01 | 2015-06-24 | Basf Se | Metodo para controlar insectos resistentes a insecticidas |
EP2903442A1 (en) | 2012-10-01 | 2015-08-12 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
WO2014053395A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Use of n-thio-anthranilamide compounds on cultivated plants |
CA2885115A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Pesticidal mixtures comprising jasmonic acid or a derivative thereof |
WO2014053407A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
WO2014053401A2 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of improving plant health |
CN104768379A (zh) | 2012-10-01 | 2015-07-08 | 巴斯夫欧洲公司 | 控制鱼尼汀-调节剂杀虫剂耐药性昆虫的方法 |
AR094139A1 (es) | 2012-10-01 | 2015-07-15 | Basf Se | Mezclas activas como plaguicidas, que comprenden compuestos de antranilamida |
JP6313312B2 (ja) | 2012-10-02 | 2018-04-18 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 農薬としての複素環化合物 |
WO2014060381A1 (de) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
US20150284380A1 (en) | 2012-10-31 | 2015-10-08 | Bayer Cropscience Ag | Novel heterocyclic compounds as pest control agents |
DE102012021647A1 (de) | 2012-11-03 | 2014-05-08 | Clariant International Ltd. | Wässrige Adjuvant-Zusammensetzungen |
UA117816C2 (uk) | 2012-11-06 | 2018-10-10 | Байєр Кропсайєнс Акцієнгезелльшафт | Гербіцидна комбінація для толерантних соєвих культур |
WO2014079841A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
ES2785070T3 (es) | 2012-11-22 | 2020-10-05 | Basf Corp | Mezclas de pesticidas |
WO2014079770A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079766A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079728A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079804A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079820A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Use of anthranilamide compounds for reducing insect-vectored viral infections |
WO2014079774A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079772A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079752A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079813A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
CN104837351A (zh) | 2012-11-30 | 2015-08-12 | 拜耳作物科学股份公司 | 二元杀真菌或杀虫混合物 |
CA2892701A1 (en) * | 2012-11-30 | 2014-06-05 | Bayer Cropscience Ag | Binary pesticidal and fungicidal mixtures |
CA3105365A1 (en) | 2012-11-30 | 2014-06-05 | Bayer Cropscience Ag | Binary fungicidal mixtures |
US20150289518A1 (en) | 2012-12-03 | 2015-10-15 | Bayer Cropscience Ag | Composition comprising a biological control agent and an insecticide |
WO2014086753A2 (en) | 2012-12-03 | 2014-06-12 | Bayer Cropscience Ag | Composition comprising biological control agents |
WO2014086758A2 (en) | 2012-12-03 | 2014-06-12 | Bayer Cropscience Ag | Composition comprising a biological control agent and an insecticide |
CA2893083A1 (en) | 2012-12-03 | 2014-06-12 | Bayer Cropscience Ag | Composition comprising a biological control agent and an insecticide |
WO2014086759A2 (en) | 2012-12-03 | 2014-06-12 | Bayer Cropscience Ag | Composition comprising biological control agents |
EP2928296A1 (de) | 2012-12-05 | 2015-10-14 | Bayer CropScience AG | Verwendung substituierter 1-(arylethinyl)-, 1-(heteroarylethinyl)-, 1-(heterocyclylethinyl)- und 1-(cyloalkenylethinyl)-cyclohexanole als wirkstoffe gegen abiotischen pflanzenstress |
WO2014090765A1 (en) | 2012-12-12 | 2014-06-19 | Bayer Cropscience Ag | Use of 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-5-amino-3-trifluoromethyl)-1 h-1,2,4 tfia zole for controlling nematodes in nematode-resistant crops |
TWI623520B (zh) * | 2012-12-12 | 2018-05-11 | 德商拜耳作物科學股份有限公司 | 製備雙(3-胺基苯基)二硫化物及3-胺基硫醇之方法 |
AU2013357564A1 (en) | 2012-12-14 | 2015-07-02 | Basf Se | Malononitrile compounds for controlling animal pests |
AR093996A1 (es) | 2012-12-18 | 2015-07-01 | Bayer Cropscience Ag | Combinaciones bactericidas y fungicidas binarias |
KR20150100808A (ko) | 2012-12-21 | 2015-09-02 | 바스프 에스이 | 무척추동물 해충의 방제를 위한 시클로클라빈 및 이의 유도체 |
WO2014102244A1 (en) | 2012-12-27 | 2014-07-03 | Basf Se | 2-(pyridin-3-yl)-5-hetaryl-thiazole compounds carrying an imine or imine-derived substituent for combating invertebrate pests |
SI2953942T1 (en) | 2013-02-06 | 2018-03-30 | Bayer Cropscience Ag | Halogen-substituted pyrazole derivatives such as pesticides |
WO2014124373A1 (en) | 2013-02-11 | 2014-08-14 | Bayer Cropscience Lp | Compositions comprising gougerotin and an insecticide |
CA2899303A1 (en) | 2013-02-11 | 2014-08-14 | Bayer Cropscience Lp | Compositions comprising gougerotin and a biological control agent |
WO2014128136A1 (en) | 2013-02-20 | 2014-08-28 | Basf Se | Anthranilamide compounds and their use as pesticides |
US20160024108A1 (en) | 2013-03-12 | 2016-01-28 | Bayer Cropscience Aktiengesellschaft | Use of dithiine-tetracarboximides for controlling bacterial harmful organisms in useful plants |
AU2014230766B2 (en) | 2013-03-13 | 2017-11-23 | Discovery Purchaser Corporation | Lawn growth-promoting agent and method of using same |
ES2630373T3 (es) | 2013-04-19 | 2017-08-21 | Basf Se | Compuestos y derivados de acil-imino-piridina N-sustituidos para combatir plagas animales |
WO2014170313A1 (en) | 2013-04-19 | 2014-10-23 | Bayer Cropscience Ag | Active compound combinations having insecticidal properties |
WO2014170364A1 (en) | 2013-04-19 | 2014-10-23 | Bayer Cropscience Ag | Binary insecticidal or pesticidal mixture |
CN105722830B (zh) * | 2013-06-20 | 2019-06-04 | 拜耳作物科学股份公司 | 作为杀螨剂和杀昆虫剂的芳基硫醚衍生物和芳基亚砜衍生物 |
ES2761571T3 (es) | 2013-06-20 | 2020-05-20 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido como acaricidas e insecticidas |
WO2014202751A1 (en) | 2013-06-21 | 2014-12-24 | Basf Se | Methods for controlling pests in soybean |
TW201542532A (zh) * | 2013-07-08 | 2015-11-16 | Bayer Cropscience Ag | 作為殺蟲劑的六員c-n-鍵結之芳基硫化物及芳基亞碸衍生物 |
AR097138A1 (es) | 2013-07-15 | 2016-02-24 | Basf Se | Compuestos plaguicidas |
WO2015036380A1 (de) | 2013-09-13 | 2015-03-19 | Bayer Cropscience Ag | Verfahren zur reduktion von arylsulfoxiden zu arylthioethern |
UA117681C2 (uk) | 2013-09-19 | 2018-09-10 | Басф Се | N-ациліміногетероциклічні сполуки |
UY35772A (es) | 2013-10-14 | 2015-05-29 | Bayer Cropscience Ag | Nuevos compuestos plaguicidas |
WO2015055554A1 (de) | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff für die saatgut- und bodenbehandlung |
WO2015055497A1 (en) | 2013-10-16 | 2015-04-23 | Basf Se | Substituted pesticidal pyrazole compounds |
AU2014336140B9 (en) | 2013-10-18 | 2018-07-19 | Basf Agrochemical Products B.V. | Use of pesticidal active carboxamide derivative in soil and seed application and treatment methods |
US9936700B2 (en) | 2013-10-23 | 2018-04-10 | Bayer Cropscience Aktiengesellschaft | Substituted quinoxaline derivatives as pest control agent |
CN105829296A (zh) | 2013-12-18 | 2016-08-03 | 巴斯夫欧洲公司 | 带有亚胺衍生的取代基的唑类化合物 |
JP2017502022A (ja) | 2013-12-18 | 2017-01-19 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | N−置換イミノ複素環式化合物 |
RU2016131792A (ru) | 2014-01-03 | 2018-02-06 | Байер Энимэл Хельс ГмбХ | Новые пиразолил-гетероариламиды в качестве средств для борьбы с вредителями |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
AR099120A1 (es) | 2014-01-20 | 2016-06-29 | Bayer Cropscience Ag | Derivados de quinolina como insecticidas y acaricidas |
DE202014008418U1 (de) | 2014-02-19 | 2014-11-14 | Clariant International Ltd. | Schaumarme agrochemische Zusammensetzungen |
DE202014008415U1 (de) | 2014-02-19 | 2014-11-25 | Clariant International Ltd. | Wässrige Adjuvant-Zusammensetzung zur Wirkungssteigerung von Elektrolyt-Wirkstoffen |
WO2015135984A1 (de) * | 2014-03-13 | 2015-09-17 | Bayer Cropscience Ag | Verfahren zur herstellung von chiralen 3-(5-aminotriazolyl)-sulfoxid-derivaten |
ES2819505T3 (es) | 2014-04-02 | 2021-04-16 | Bayer Cropscience Ag | Derivados de N-(1-(hetero)aril-1H-pirazol-4-il)-(hetero)arilamida y su uso como pesticidas |
WO2015160618A1 (en) | 2014-04-16 | 2015-10-22 | Bayer Cropscience Lp | Compositions comprising ningnanmycin and a biological control agent |
WO2015160620A1 (en) | 2014-04-16 | 2015-10-22 | Bayer Cropscience Lp | Compositions comprising ningnanmycin and an insecticide |
DE102014005771A1 (de) | 2014-04-23 | 2015-10-29 | Clariant International Ltd. | Verwendung von wässrigen driftreduzierenden Zusammensetzungen |
EP3139743B1 (en) | 2014-05-08 | 2018-03-14 | Bayer CropScience Aktiengesellschaft | Pyrazolopyridine sulfonamides as nematicides |
BR112016028404A2 (pt) | 2014-06-05 | 2018-07-03 | Bayer Cropscience Aktiengesellschaft | compostos bicíclicos como pesticidas |
WO2016001119A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
WO2016001129A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Verbesserte insektizide zusammensetzungen |
WO2016001124A1 (de) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide wirkstoffkombinationen |
US10208015B2 (en) | 2014-07-15 | 2019-02-19 | Bayer Animal Health Gmbh | Aryl-triazolyl pyridines as pest control agents |
DE102014012022A1 (de) | 2014-08-13 | 2016-02-18 | Clariant International Ltd. | Organische Ammoniumsalze von anionischen Pestiziden |
EP3002279A1 (de) | 2014-10-02 | 2016-04-06 | Bayer CropScience AG | Verfahren zur Herstellung von 3-(5-Aminotriazolyl)-Sulfid-Derivaten |
US10149477B2 (en) | 2014-10-06 | 2018-12-11 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
WO2016055096A1 (en) | 2014-10-07 | 2016-04-14 | Bayer Cropscience Ag | Method for treating rice seed |
BR112017009513A2 (pt) | 2014-11-06 | 2018-02-06 | Basf Se | utilização de um composto heterobicíclico, utilização dos compostos i, compostos, composição agrícola ou veterinária, método para o combate ou controle de pragas, método para a proteção de culturas e sementes |
AR102942A1 (es) | 2014-12-11 | 2017-04-05 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido de cinco miembros c-n-conectados, como plaguicidas |
DE102014018274A1 (de) | 2014-12-12 | 2015-07-30 | Clariant International Ltd. | Zuckertenside und deren Verwendung in agrochemischen Zusammensetzungen |
CN107105674B (zh) | 2014-12-22 | 2020-10-02 | 拜耳作物科学有限合伙公司 | 使用枯草芽孢杆菌或短小芽孢杆菌菌株治疗或预防凤梨病的方法 |
EP3081085A1 (en) | 2015-04-14 | 2016-10-19 | Bayer CropScience AG | Method for improving earliness in cotton |
TWI696612B (zh) * | 2015-01-29 | 2020-06-21 | 日商日本農藥股份有限公司 | 具有環烷基吡啶基的稠合雜環化合物或其鹽類及含有該化合物的農園藝用殺蟲劑以及其使用方法 |
UY36547A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
UY36548A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
EP3253209A1 (en) | 2015-02-06 | 2017-12-13 | Basf Se | Pyrazole compounds as nitrification inhibitors |
TWI702212B (zh) | 2015-02-09 | 2020-08-21 | 德商拜耳作物科學股份有限公司 | 作為除害劑之經取代的2-硫基咪唑基羧醯胺類 |
WO2016128261A2 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide |
ES2836399T3 (es) | 2015-03-10 | 2021-06-25 | Bayer Animal Health Gmbh | Derivados de pirazolilo como agentes de control de plagas |
US11064696B2 (en) | 2015-04-07 | 2021-07-20 | Basf Agrochemical Products B.V. | Use of an insecticidal carboxamide compound against pests on cultivated plants |
US10188108B2 (en) | 2015-04-08 | 2019-01-29 | Bayer Cropscience Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
WO2016174049A1 (en) | 2015-04-30 | 2016-11-03 | Bayer Animal Health Gmbh | Anti-parasitic combinations including halogen-substituted compounds |
EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
AR104596A1 (es) | 2015-05-12 | 2017-08-02 | Basf Se | Compuestos de tioéter como inhibidores de la nitrificación |
KR20180005244A (ko) | 2015-05-13 | 2018-01-15 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 살충성 아릴피롤리딘, 그의 제조 방법 및 동물 해충 방제제로서의 그의 용도 |
WO2016198611A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino heterocyclic compounds |
WO2016198613A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino compounds |
KR20180025949A (ko) | 2015-07-06 | 2018-03-09 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 농약으로서의 헤테로사이클릭 화합물 |
WO2017016883A1 (en) | 2015-07-24 | 2017-02-02 | Basf Se | Process for preparation of cyclopentene compounds |
ES2882667T3 (es) | 2015-08-07 | 2021-12-02 | Bayer Cropscience Ag | Derivados heterocíclicos condensados sustituidos por 2-(het)arilo como pesticidas |
CA2999378A1 (en) | 2015-10-02 | 2017-04-06 | Basf Se | Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents |
DE102015219651A1 (de) | 2015-10-09 | 2017-04-13 | Clariant International Ltd. | Zusammensetzungen enthaltend Zuckeramin und Fettsäure |
DE202015008045U1 (de) | 2015-10-09 | 2015-12-09 | Clariant International Ltd. | Universelle Pigmentdispersionen auf Basis von N-Alkylglukaminen |
MX2018005115A (es) | 2015-10-26 | 2018-05-28 | Bayer Cropscience Ag | Derivados de heterociclos biciclicos condensados como agentes de control de plagas. |
CN113303339A (zh) | 2015-11-30 | 2021-08-27 | 巴斯夫欧洲公司 | 顺式-茉莉酮和解淀粉芽孢杆菌的混合物 |
WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
MX2018006749A (es) | 2015-12-03 | 2018-08-15 | Bayer Cropscience Ag | Derivados de 3-(acetil)-1-[(1,3-tiazol-5-il)metil]-1h-imidazo[1,2- a]piridin-4-io-2-olato halogenados mesoionicos y compuestos relacionados como insecticidas. |
BR112018016364A2 (pt) | 2016-02-11 | 2018-12-18 | Bayer Cropscience Aktiengesellschaft | 2-oxiimidazolilcarboxamidas substituídas como pesticidas |
AU2017217183A1 (en) | 2016-02-11 | 2018-08-23 | Bayer Cropscience Aktiengesellschaft | Substituted 2-(het)aryl-imidazolyl-carboxyamides as pest control agents |
WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
AU2017221988B2 (en) * | 2016-02-26 | 2019-02-14 | Nihon Nohyaku Co., Ltd. | Benzoxazole compound or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide |
EP3210468A1 (de) | 2016-02-26 | 2017-08-30 | Bayer CropScience Aktiengesellschaft | Lösungsmittelfreie formulierungen von niedrig schmelzenden wirkstoffen |
US20190077809A1 (en) | 2016-03-09 | 2019-03-14 | Basf Se | Spirocyclic Derivatives |
BR112018068042A2 (pt) | 2016-03-11 | 2019-01-08 | Basf Se | métodos para controlar pragas de plantas, material de propagação de planta e uso de um ou mais compostos de fórmula i |
MX2018011214A (es) | 2016-03-15 | 2019-03-28 | Bayer Cropscience Ag | Sulfonamidas sustituidas para controlar plagas animales. |
CN109071444A (zh) | 2016-03-16 | 2018-12-21 | 拜耳作物科学股份公司 | 作为农药和植物保护剂的n-(氰苄基)-6-(环丙基-羰基氨基)-4-(苯基)-吡啶-2-羧酰胺衍生物及相关化合物 |
PE20181898A1 (es) | 2016-04-01 | 2018-12-11 | Basf Se | Compuestos biciclicos |
WO2017174414A1 (de) | 2016-04-05 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Naphthalin-derivate als schädlingsbekämpfungsmittel |
PL3442974T3 (pl) | 2016-04-15 | 2023-12-04 | Elanco Animal Health Gmbh | Pochodne pirazolopirymidyny |
WO2017186543A2 (en) | 2016-04-24 | 2017-11-02 | Bayer Cropscience Aktiengesellschaft | Use of fluopyram and/or bacillus subtilis for controlling fusarium wilt in plants of the musaceae family |
SI3448845T1 (sl) | 2016-04-25 | 2020-12-31 | Bayer Cropscience Aktiengesellschaft | Substituirani 2-alkilimidazolil-karboksamidi kot pesticidi |
EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
DE102016207877A1 (de) | 2016-05-09 | 2017-11-09 | Clariant International Ltd | Stabilisatoren für Silikatfarben |
WO2017198449A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in brassicaceae |
WO2017198450A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in maize |
EP3245865A1 (en) | 2016-05-17 | 2017-11-22 | Bayer CropScience Aktiengesellschaft | Method for increasing yield in brassicaceae |
WO2017198453A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in potato, tomato or alfalfa |
WO2017198452A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in soybean |
WO2017198454A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in cotton |
WO2017198451A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in small grain cereals such as wheat and rice |
WO2017198455A2 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in beta spp. plants |
CA3024100A1 (en) | 2016-05-18 | 2017-11-23 | Basf Se | Capsules comprising benzylpropargylethers for use as nitrification inhibitors |
US10653135B2 (en) | 2016-07-11 | 2020-05-19 | Covestro Llc | Methods for treating seeds with an aqueous composition and seeds treated therewith |
US10653136B2 (en) | 2016-07-11 | 2020-05-19 | Covestro Llc | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
US10750750B2 (en) | 2016-07-11 | 2020-08-25 | Covestro Llc | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
MX2019000512A (es) | 2016-07-12 | 2019-05-02 | Bayer Cropscience Ag | Compuestos biciclicos como plaguicidas. |
US10561145B2 (en) | 2016-07-19 | 2020-02-18 | Bayer Cropscience Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
CN106349236B (zh) * | 2016-07-28 | 2018-11-16 | 中国农业大学 | 1h-1,2,4-三唑脒类化合物及其制备方法和应用 |
US20190159451A1 (en) | 2016-07-29 | 2019-05-30 | Bayer Cropscience Aktiengesellschaft | Active compound combinations and methods to protect the propagation material of plants |
BR112019001766B1 (pt) | 2016-07-29 | 2022-12-06 | Bayer Cropscience Aktiengesellschaft | Semente revestida tratada para melhorar o seu crescimento, seu método de tratamento, e método para melhorar crescimento de planta |
CN109843878A (zh) | 2016-08-10 | 2019-06-04 | 拜耳作物科学股份公司 | 用作害虫防治剂的取代的2-杂环基咪唑基甲酰胺 |
BR112019003158B1 (pt) | 2016-08-15 | 2022-10-25 | Bayer Cropscience Aktiengesellschaft | Derivados de heterociclo bicíclico condensado, seu uso, formulação agroquímica, e método para controlar pragas animais |
CN109963860A (zh) | 2016-09-19 | 2019-07-02 | 拜耳作物科学股份公司 | 吡唑并[1,5-a]吡啶衍生物及其作为农药的用途 |
AU2017340690B2 (en) | 2016-10-06 | 2021-05-20 | Bayer Cropscience Aktiengesellschaft | 2-(Het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents |
WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
WO2018069106A1 (en) | 2016-10-10 | 2018-04-19 | Basf Se | Pesticidal mixture |
CA3040408A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
CN109843056A (zh) | 2016-10-14 | 2019-06-04 | 印度商皮埃企业有限公司 | 4-经取代之苯基胺衍生物及其通过对抗不要的植物病原性微生物而保护作物之用途 |
TW201822637A (zh) | 2016-11-07 | 2018-07-01 | 德商拜耳廠股份有限公司 | 用於控制動物害蟲的經取代磺醯胺類 |
US10889573B2 (en) | 2016-11-11 | 2021-01-12 | Bayer Animal Health Gmbh | Anthelmintic quinoline-3-carboxamide derivatives |
KR20190084310A (ko) | 2016-11-23 | 2019-07-16 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 살충제로서의 2-[3-(알킬술포닐)-2H-인다졸-2-일]-3H-이미다조[4,5-b]피리딘 유도체 및 유사한 화합물 |
EP3400801A1 (en) | 2017-05-10 | 2018-11-14 | Bayer CropScience Aktiengesellschaft | Plant health effect of purpureocillium lilacinum |
JP2020502110A (ja) | 2016-12-16 | 2020-01-23 | バイエル・アクチエンゲゼルシヤフト | 殺虫剤として使用するためのメソイオン性イミダゾピリジン類 |
BR112019011211A2 (pt) | 2016-12-16 | 2019-10-15 | Basf Se | compostos de fórmula i, composição, métodos para combater ou controlar pragas invertebradas, para proteger plantas em crescimento de ataque ou infestação por pragas invertebradas, semente, uso de um composto e método para tratar ou proteger um animal |
EP3555089A1 (en) | 2016-12-16 | 2019-10-23 | Bayer CropScience Aktiengesellschaft | Thiadiazole derivatives as pesticides |
WO2018116072A1 (en) | 2016-12-20 | 2018-06-28 | Pi Industries Ltd. | Heterocyclic compounds |
WO2018116073A1 (en) | 2016-12-21 | 2018-06-28 | Pi Industries Ltd. | 1, 2, 3-thiadiazole compounds and their use as crop protecting agent |
US11083199B2 (en) | 2017-01-10 | 2021-08-10 | Bayer Aktiengesellschaft | Heterocycle derivatives as pesticides |
JP7101177B2 (ja) | 2017-01-10 | 2022-07-14 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としてのヘテロサイクレン誘導体 |
WO2018138050A1 (de) | 2017-01-26 | 2018-08-02 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
TW201833107A (zh) | 2017-02-06 | 2018-09-16 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之經2-(雜)芳基取代的稠合雜環衍生物 |
EP3369320A1 (de) | 2017-03-02 | 2018-09-05 | Bayer CropScience Aktiengesellschaft | Wirkstoff zur bekämpfung von wanzen |
WO2018162312A1 (en) | 2017-03-10 | 2018-09-13 | Basf Se | Spirocyclic derivatives |
WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
JP7160486B2 (ja) | 2017-03-28 | 2022-10-25 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺生物剤化合物 |
EP3601279B1 (de) | 2017-03-31 | 2023-10-18 | Bayer Animal Health GmbH | Trizyklische carboxamide zur bekämpfung von arthropoden |
JP7161823B2 (ja) | 2017-03-31 | 2022-10-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 動物有害生物を駆除するためのピリミジニウム化合物及びそれらの混合物 |
WO2018177993A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazole zur bekämpfung von arthropoden |
WO2018189077A1 (de) | 2017-04-12 | 2018-10-18 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
WO2018192793A1 (en) | 2017-04-20 | 2018-10-25 | Basf Se | Substituted rhodanine derivatives |
CA3059301A1 (en) | 2017-04-20 | 2018-10-25 | Pi Industries Ltd. | Novel phenylamine compounds |
BR112019021803A2 (pt) | 2017-04-21 | 2020-05-05 | Bayer Ag | imidazopiridinas mesoiônicas como inseticidas |
US20200128830A1 (en) | 2017-04-24 | 2020-04-30 | Bayer Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
EP3615530B1 (en) | 2017-04-26 | 2021-04-14 | Basf Se | Substituted succinimide derivatives as pesticides |
TWI782983B (zh) | 2017-04-27 | 2022-11-11 | 德商拜耳廠股份有限公司 | 雜芳基苯基胺基喹啉及類似物 |
AU2018257582B2 (en) | 2017-04-27 | 2022-06-16 | Bayer Animal Health Gmbh | New bicyclic pyrazole derivatives |
KR20200003047A (ko) | 2017-05-02 | 2020-01-08 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 2-(헤트)아릴-치환된 축합된 비시클릭 헤테로시클릭 유도체 |
ES2884902T3 (es) | 2017-05-02 | 2021-12-13 | Bayer Ag | Derivados de heterociclos condensados sustituidos con 2-(het)arilo como pesticidas |
JP2020518589A (ja) | 2017-05-03 | 2020-06-25 | バイエル・アクチエンゲゼルシヤフト | トリ置換シリルベンジルベンゾイミダゾール類及び類縁体 |
JP2020518592A (ja) | 2017-05-03 | 2020-06-25 | バイエル・アクチエンゲゼルシヤフト | トリ置換シリルヘテロアリールオキシキノリン類及び類縁体 |
BR112019023030A2 (pt) | 2017-05-03 | 2020-06-02 | Bayer Aktiengesellschaft | Sililmetilfenoxiquinolinas trissubstituídas e análogos |
CN110869349A (zh) | 2017-05-04 | 2020-03-06 | 拜耳作物科学股份公司 | 作为例如用于保护植物的害虫防治剂的2-{[2-(苯氧基甲基)吡啶-5-基]氧基}乙胺衍生物及相关化合物 |
WO2018202525A1 (en) | 2017-05-04 | 2018-11-08 | Bayer Cropscience Aktiengesellschaft | Phenoxyethanamine derivatives for controlling pests |
RU2019139232A (ru) | 2017-05-10 | 2021-06-10 | Басф Се | Бициклические пестицидные соединения |
WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
CN110770235A (zh) | 2017-06-16 | 2020-02-07 | 巴斯夫欧洲公司 | 用于防除动物害虫的介离子咪唑鎓化合物和衍生物 |
EP3642203A1 (en) | 2017-06-19 | 2020-04-29 | Basf Se | Substituted pyrimidinium compounds and derivatives for combating animal pests |
WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | SUBSTITUTED CYCLOPROPYL DERIVATIVES |
KR20200020911A (ko) | 2017-06-30 | 2020-02-26 | 바이엘 애니멀 헬스 게엠베하 | 새로운 아자퀴놀린 유도체 |
WO2019007891A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2019007888A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2019007887A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
WO2019007719A1 (en) | 2017-07-07 | 2019-01-10 | Basf Se | PESTICIDE MIXTURES |
EP3284739A1 (de) | 2017-07-19 | 2018-02-21 | Bayer CropScience Aktiengesellschaft | Substituierte (het)arylverbindungen als schädlingsbekämpfungsmittel |
JP7455294B2 (ja) | 2017-08-04 | 2024-03-26 | エランコ アニマル ヘルス ゲー・エム・ベー・ハー | 蠕虫による感染を治療するためのキノリン誘導体 |
US11849724B2 (en) | 2017-08-17 | 2023-12-26 | Bayer Cropscience Lp | Liquid fertilizer-dispersible compositions and methods thereof |
US11655258B2 (en) | 2017-08-22 | 2023-05-23 | Bayer Aktiengesellschaft | Heterocycle derivatives as pesticides |
WO2019042932A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING RICE PARASITES IN RICE |
EP3453706A1 (en) | 2017-09-08 | 2019-03-13 | Basf Se | Pesticidal imidazole compounds |
RU2770703C2 (ru) | 2017-09-20 | 2022-04-21 | Митсуй Кемикалс Агро, Инк. | Агент, контролирующий эктопаразитов, длительного действия для животного |
BR112020006659B1 (pt) | 2017-10-04 | 2022-01-25 | Bayer Aktiengesellschaft | Derivados de compostos heterocíclicos, formulação agroquímica, método para controlar uma ou mais pragas animais, e produto |
CN111201227B (zh) | 2017-10-13 | 2024-03-15 | 巴斯夫欧洲公司 | 用于防除动物害虫的咪唑烷嘧啶鎓化合物 |
EP3473103A1 (de) | 2017-10-17 | 2019-04-24 | Bayer AG | Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinon |
EP3473100A1 (en) | 2017-10-18 | 2019-04-24 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
AR113445A1 (es) | 2017-10-18 | 2020-05-06 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas / acaricidas |
MX2020004070A (es) | 2017-10-18 | 2020-07-28 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas/acaricidas. |
US11540517B2 (en) | 2017-10-18 | 2023-01-03 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
TWI804516B (zh) | 2017-10-18 | 2023-06-11 | 德商拜耳廠股份有限公司 | 具有殺昆蟲/殺蟎性質之活性化合物組合(二) |
WO2019076751A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES |
US11213031B2 (en) | 2017-11-13 | 2022-01-04 | Bayer Aktiengesellschaft | Tetrazolylpropyl derivatives and their use as fungicides |
BR112020010452A2 (pt) | 2017-11-28 | 2020-10-20 | Bayer Aktiengesellschaft | compostos heterocíclicos como pesticidas |
AU2018376146A1 (en) | 2017-11-29 | 2020-05-28 | Bayer Aktiengesellschaft | Nitrogenous heterocycles as a pesticide |
WO2019121143A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Substituted cyclopropyl derivatives |
WO2019123196A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Fluoralkenyl compounds, process for preparation and use thereof |
BR112020012566B1 (pt) | 2017-12-21 | 2024-03-05 | Basf Se | Composto da fórmula i, composição, método de combate ou controle de pragas invertebradas, método de proteção de plantas em crescimento contra ataque ou infestação por pragas invertebradas, semente revestida, e usos de um composto da fórmula i |
TW201927768A (zh) | 2017-12-21 | 2019-07-16 | 德商拜耳廠股份有限公司 | 三取代矽基甲基雜芳氧基喹啉及類似物 |
CA3087313A1 (en) | 2018-01-09 | 2019-08-01 | Basf Se | Silylethynyl hetaryl compounds as nitrification inhibitors |
WO2019137995A1 (en) | 2018-01-11 | 2019-07-18 | Basf Se | Novel pyridazine compounds for controlling invertebrate pests |
EP3305786A3 (de) | 2018-01-22 | 2018-07-25 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019150311A1 (en) | 2018-02-02 | 2019-08-08 | Pi Industries Ltd. | 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms |
US20210009541A1 (en) | 2018-02-12 | 2021-01-14 | Bayer Aktiengesellschaft | Fungicidal oxadiazoles |
WO2019162228A1 (en) | 2018-02-21 | 2019-08-29 | Bayer Aktiengesellschaft | 1-(5-substituted imidazol-1-yl)but-3-en derivatives and their use as fungicides |
WO2019162174A1 (de) | 2018-02-21 | 2019-08-29 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
CA3089381A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of pyrazole propargyl ethers as nitrification inhibitors |
JP7440418B2 (ja) | 2018-02-28 | 2024-02-28 | ビーエーエスエフ ソシエタス・ヨーロピア | 硝化阻害剤としてのアルコキシピラゾールの使用 |
KR20200128405A (ko) | 2018-02-28 | 2020-11-12 | 바스프 에스이 | 질화작용 저해제로서의 n-관능화 알콕시 피라졸 화합물의 용도 |
KR20200129128A (ko) | 2018-03-08 | 2020-11-17 | 바이엘 악티엔게젤샤프트 | 식물 보호에서 살충제로서의 헤테로아릴-트리아졸 및 헤테로아릴-테트라졸 화합물의 용도 |
US11414432B2 (en) | 2018-03-12 | 2022-08-16 | Bayer Aktiengesellschaft | Condensed bicyclic heterocyclic derivatives as pest control agents |
WO2019175712A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways |
WO2019175713A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
WO2019185413A1 (en) | 2018-03-27 | 2019-10-03 | Basf Se | Pesticidal substituted cyclopropyl derivatives |
CN108373453B (zh) * | 2018-04-03 | 2020-04-17 | 苏州大学张家港工业技术研究院 | 三氮唑衍生物及其制备方法 |
CA3096497A1 (en) | 2018-04-10 | 2019-10-17 | Bayer Aktiengesellschaft | Oxadiazoline derivatives |
IL277777B2 (en) | 2018-04-12 | 2023-10-01 | Bayer Ag | N-(cyclopropylmethyl)-5-(methylsulfonyl)-N-{1-[1-(pyrimidin-2-yl)-H1-1, 2, 4-triazol-5-yl]ethyl}benzamide derivatives and pyridinecarboxamide derivatives Compatible as pest killers |
WO2019197615A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit fungiziden, insektiziden und akariziden eigenschaften |
US20210068396A1 (en) | 2018-04-13 | 2021-03-11 | Bayer Aktiengesellschaft | Active ingredient combinations with insecticidal, nematicidal and acaricidal properties |
UY38184A (es) | 2018-04-17 | 2019-10-31 | Bayer Ag | Compuestos heteroarilo-triazol y heteroarilo-tetrazol novedosos como plaguicidas |
JP2021522181A (ja) | 2018-04-20 | 2021-08-30 | バイエル・アクチエンゲゼルシヤフト | 殺有害生物剤としてのヘテロアリール−トリアゾール化合物及びヘテロアリール−テトラゾール化合物 |
JP2021522182A (ja) | 2018-04-20 | 2021-08-30 | バイエル・アクチエンゲゼルシヤフト | 殺有害生物剤としてのヘテロシクレン誘導体 |
US11528907B2 (en) | 2018-04-25 | 2022-12-20 | Bayer Aktiengesellschaft | Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
MX2020011873A (es) | 2018-05-09 | 2021-01-20 | Bayer Animal Health Gmbh | Nuevos derivados de quinolina. |
CN112423590B (zh) | 2018-05-15 | 2022-07-08 | 巴斯夫欧洲公司 | 包含benzpyrimoxan和oxazosulfyl的混合物和用途以及它们的施用方法 |
WO2019224092A1 (en) | 2018-05-22 | 2019-11-28 | Basf Se | Pesticidally active c15-derivatives of ginkgolides |
WO2019224143A1 (de) | 2018-05-24 | 2019-11-28 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
EP3809844A1 (en) | 2018-06-25 | 2021-04-28 | Bayer CropScience LP | Seed treatment method |
WO2020002189A1 (de) | 2018-06-27 | 2020-01-02 | Bayer Aktiengesellschaft | Wirkstoffkombinationen |
WO2020002472A1 (en) | 2018-06-28 | 2020-01-02 | Basf Se | Use of alkynylthiophenes as nitrification inhibitors |
EP3586630A1 (en) | 2018-06-28 | 2020-01-01 | Bayer AG | Active compound combinations having insecticidal/acaricidal properties |
US20230159486A1 (en) | 2018-07-05 | 2023-05-25 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides and analogues as antibacterials agents |
EP3826983A1 (en) | 2018-07-23 | 2021-06-02 | Basf Se | Use of substituted 2-thiazolines as nitrification inhibitors |
WO2020020765A1 (en) | 2018-07-23 | 2020-01-30 | Basf Se | Use of a substituted thiazolidine compound as nitrification inhibitor |
WO2020020813A1 (en) | 2018-07-25 | 2020-01-30 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
WO2020020816A1 (en) | 2018-07-26 | 2020-01-30 | Bayer Aktiengesellschaft | Novel triazole derivatives |
US20210321610A1 (en) | 2018-07-27 | 2021-10-21 | Bayer Aktiengesellschaft | Controlled release formulations for agrochemicals |
BR112021001633A2 (pt) | 2018-07-31 | 2021-05-04 | Bayer Aktiengesellschaft | formulações de liberação controlada com lignina para agroquímicos |
AR115984A1 (es) | 2018-08-17 | 2021-03-17 | Pi Industries Ltd | Compuestos de 1,2-ditiolona y sus usos |
EP3613736A1 (en) | 2018-08-22 | 2020-02-26 | Basf Se | Substituted glutarimide derivatives |
WO2020043650A1 (en) | 2018-08-29 | 2020-03-05 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
JP2022500412A (ja) | 2018-09-13 | 2022-01-04 | バイエル・アクチエンゲゼルシヤフト | 害虫防除剤としての複素環誘導体 |
TW202023386A (zh) * | 2018-09-13 | 2020-07-01 | 瑞士商先正達合夥公司 | 殺有害生物活性唑-醯胺化合物 |
CN112714614A (zh) | 2018-09-17 | 2021-04-27 | 拜耳公司 | 杀真菌剂异氟普仑用于在谷物中防治麦角菌和减少菌核的用途 |
BR112021004526A2 (pt) | 2018-09-28 | 2021-06-08 | Basf Se | uso do composto, métodos de proteção de plantas, de controle ou combate a pragas invertebradas e de tratamento de sementes e semente |
EP3628157A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
EP3628158A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
EP3628156A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants |
WO2020070050A1 (en) | 2018-10-01 | 2020-04-09 | Bayer Aktiengesellschaft | Fungicidal 5-substituted imidazol-1-yl carbinol derivatives |
EP3636644A1 (de) | 2018-10-11 | 2020-04-15 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
WO2020078839A1 (de) | 2018-10-16 | 2020-04-23 | Bayer Aktiengesellschaft | Wirkstoffkombinationen |
JP2022512719A (ja) | 2018-10-18 | 2022-02-07 | バイエル・アクチエンゲゼルシヤフト | ピリジルフェニルアミノキノリン類及び類似体 |
US20210387964A1 (en) | 2018-10-18 | 2021-12-16 | Bayer Aktiengesellschaft | Heteroarylaminoquinolines and analogues |
TW202028193A (zh) | 2018-10-20 | 2020-08-01 | 德商拜耳廠股份有限公司 | 氧雜環丁基苯氧基喹啉及類似物 |
EP3643711A1 (en) | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
EP3643705A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
WO2020109039A1 (en) | 2018-11-28 | 2020-06-04 | Basf Se | Pesticidal compounds |
AR117169A1 (es) | 2018-11-28 | 2021-07-14 | Bayer Ag | (tio)amidas de piridazina como compuestos fungicidas |
PL3890489T3 (pl) | 2018-12-07 | 2023-05-08 | Bayer Aktiengesellschaft | Kompozycje herbicydowe |
FI3890488T3 (fi) | 2018-12-07 | 2023-03-30 | Bayer Ag | Rikkakasveja torjuvia koostumuksia |
EP3620052A1 (en) | 2018-12-12 | 2020-03-11 | Bayer Aktiengesellschaft | Use of phenoxypyridinyl-substituted (1h-1,2,4-triazol-1-yl)alcohols for controlling fungicidal diseases in maize |
WO2020126980A1 (en) | 2018-12-18 | 2020-06-25 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
CN113195491A (zh) | 2018-12-18 | 2021-07-30 | 巴斯夫欧洲公司 | 用于防除动物害虫的取代嘧啶鎓化合物 |
BR112021010152A2 (pt) | 2018-12-20 | 2021-11-09 | Bayer Ag | Heterociclil piridazina como compostos fungicidas |
EP3669652A1 (en) | 2018-12-21 | 2020-06-24 | Bayer AG | Active compound combination |
CN113473860A (zh) | 2018-12-21 | 2021-10-01 | 拜耳公司 | 作为新的抗真菌剂的1,3,4-噁二唑及其衍生物 |
EP3679792A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679790A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679789A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679793A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679791A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3696177A1 (en) | 2019-02-12 | 2020-08-19 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
EP3545764A1 (en) | 2019-02-12 | 2019-10-02 | Bayer AG | Crystal form of 2-({2-fluoro-4-methyl-5-[(r)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2- trifluoroethyl)-1,3-thiazolidin-4-one |
US20230060425A1 (en) | 2019-02-26 | 2023-03-02 | Bayer Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
KR20210133984A (ko) | 2019-02-26 | 2021-11-08 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 축합된 비시클릭 헤테로시클릭 유도체 |
US20220132851A1 (en) | 2019-03-01 | 2022-05-05 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
AR118247A1 (es) | 2019-03-05 | 2021-09-22 | Bayer Ag | Combinación de compuestos activos |
WO2020182929A1 (en) | 2019-03-13 | 2020-09-17 | Bayer Aktiengesellschaft | Substituted ureas and derivatives as new antifungal agents |
WO2020187656A1 (en) | 2019-03-15 | 2020-09-24 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
EP3564225A1 (en) | 2019-03-21 | 2019-11-06 | Bayer Aktiengesellschaft | Crystalline form of spiromesifen |
EP3725788A1 (en) | 2019-04-15 | 2020-10-21 | Bayer AG | Novel heteroaryl-substituted aminoalkyl azole compounds as pesticides |
WO2020225431A1 (en) | 2019-05-08 | 2020-11-12 | Bayer Aktiengesellschaft | High spreading ulv formulations for fungicides |
BR112021022124A2 (pt) | 2019-05-08 | 2022-01-04 | Bayer Ag | Combinação de compostos ativos |
US20220240508A1 (en) | 2019-05-10 | 2022-08-04 | Bayer Cropscience Lp | Active compound combinations |
WO2020229398A1 (de) | 2019-05-14 | 2020-11-19 | Bayer Aktiengesellschaft | (1-alkenyl)-substituierte pyrazole und triazole als schädlingsbekämpfungsmittel |
EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2020239517A1 (en) | 2019-05-29 | 2020-12-03 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
EP3750888A1 (en) | 2019-06-12 | 2020-12-16 | Bayer Aktiengesellschaft | Crystalline form a of 1,4-dimethyl-2-[2-(pyridin-3-yl)-2h-indazol-5-yl]-1,2,4-triazolidine-3,5-dione |
BR112021025305A2 (pt) | 2019-06-21 | 2022-02-01 | Bayer Ag | Hidroxi-isoxazolinas e uso das mesmas como fungicidas |
BR112021025264A2 (pt) | 2019-06-21 | 2022-01-25 | Bayer Ag | Fenoxifenil hidróxi-isoxazolinas e análogos como novos agentes antifúngicos |
BR112021025865A2 (pt) | 2019-06-21 | 2022-03-03 | Bayer Ag | Hidróxi-isoxazolinas e derivados das mesmas |
BR112021025317A2 (pt) | 2019-06-21 | 2022-03-15 | Bayer Ag | Tienilhidroxiisoxazolinas e derivados das mesmas |
EP3986891A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
WO2020254494A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Fungicidal oxadiazoles |
EP3986874A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Benzylphenyl hydroxyisoxazolines and analogues as new antifungal agents |
EP3986877A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
AU2020301155A1 (en) | 2019-06-24 | 2022-01-27 | Auburn University | A bacillus strain and methods of its use for plant growth promotion |
CN110367255A (zh) * | 2019-06-27 | 2019-10-25 | 山东康乔生物科技有限公司 | 包含螺甲螨酯和三氟乙基硫化物类杀虫剂的协同杀虫组合物及其应用 |
EP3608311A1 (en) | 2019-06-28 | 2020-02-12 | Bayer AG | Crystalline form a of n-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide |
BR112021026696A2 (pt) | 2019-07-03 | 2022-02-15 | Bayer Ag | Tiofeno carboxamidas substituídas e derivados das mesmas |
US20220386605A1 (en) | 2019-07-04 | 2022-12-08 | Bayer Aktiengesellschaft | Herbicidal compositions |
EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
US20220289691A1 (en) | 2019-07-22 | 2022-09-15 | Bayer Aktiengesellschaft | 5-amino-substituted pyrazoles and triazoles as pest control agents |
BR112022000942A2 (pt) | 2019-07-23 | 2022-05-17 | Bayer Ag | Compostos de heteroaril-triazol como pesticidas |
AU2020317609A1 (en) | 2019-07-23 | 2022-02-24 | Bayer Aktiengesellschaft | Novel heteroaryl-triazole compounds as pesticides |
TW202120490A (zh) | 2019-07-30 | 2021-06-01 | 德商拜耳動物保健有限公司 | 新穎異喹啉衍生物 |
EP3771714A1 (de) | 2019-07-30 | 2021-02-03 | Bayer AG | Stickstoffhaltige heterocyclen als schädlingsbekämpfungsmittel |
EP3701796A1 (en) | 2019-08-08 | 2020-09-02 | Bayer AG | Active compound combinations |
US20220304305A1 (en) | 2019-09-11 | 2022-09-29 | Bayer Aktiengesellschaft | Highly effective formulations on the basis of 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinones and preemergence herbicides |
US20220403410A1 (en) | 2019-09-26 | 2022-12-22 | Bayer Aktiengesellschaft | Rnai-mediated pest control |
KR20220081359A (ko) | 2019-10-09 | 2022-06-15 | 바이엘 악티엔게젤샤프트 | 살충제로서의 신규 헤테로아릴-트리아졸 화합물 |
BR112022006774A2 (pt) | 2019-10-09 | 2022-06-28 | Bayer Ag | Compostos de heteroaril-triazol inovadores como pesticidas |
TW202128650A (zh) | 2019-10-11 | 2021-08-01 | 德商拜耳動物保健有限公司 | 作為殺蟲劑之新穎的雜芳基取代之吡𠯤衍生物 |
CN114641467A (zh) | 2019-11-07 | 2022-06-17 | 拜耳公司 | 用于防治动物有害物的取代的磺酰胺 |
WO2021097162A1 (en) | 2019-11-13 | 2021-05-20 | Bayer Cropscience Lp | Beneficial combinations with paenibacillus |
TW202134226A (zh) | 2019-11-18 | 2021-09-16 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之新穎雜芳基-三唑化合物 |
TW202136248A (zh) | 2019-11-25 | 2021-10-01 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之新穎雜芳基-三唑化合物 |
CR20220294A (es) | 2019-12-20 | 2022-08-03 | Bayer Ag | Tiofenocarboxamidas sustituidas y sus derivados |
KR20220114636A (ko) | 2019-12-20 | 2022-08-17 | 바이엘 악티엔게젤샤프트 | 티에닐옥사졸론 및 유사체 |
BR112022012469A2 (pt) | 2019-12-23 | 2022-09-06 | Basf Se | Método e composição para a proteção de plantas ou material de propagação vegetal, uso de pelo menos um composto ativo e pelo menos uma enzima, sementes e kit de partes |
EP3845304A1 (en) | 2019-12-30 | 2021-07-07 | Bayer AG | Capsule suspension concentrates based on polyisocyanates and biodegradable amine based cross-linker |
CN115551839A (zh) | 2020-02-18 | 2022-12-30 | 拜耳公司 | 作为农药的杂芳基-三唑化合物 |
EP3868207A1 (de) | 2020-02-24 | 2021-08-25 | Bayer Aktiengesellschaft | Verkapselte pyrethroide mit verbesserter wirksamkeit bei boden- und blattanwendungen |
WO2021170463A1 (en) | 2020-02-28 | 2021-09-02 | BASF Agro B.V. | Methods and uses of a mixture comprising alpha-cypermethrin and dinotefuran for controlling invertebrate pests in turf |
EP3708565A1 (en) | 2020-03-04 | 2020-09-16 | Bayer AG | Pyrimidinyloxyphenylamidines and the use thereof as fungicides |
WO2021204930A1 (en) | 2020-04-09 | 2021-10-14 | Bayer Animal Health Gmbh | Substituted condensed azines as anthelmintic compounds |
WO2021209366A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
CN115551355A (zh) | 2020-04-16 | 2022-12-30 | 拜耳公司 | 活性化合物结合物和包含它们的杀真菌剂组合物 |
EP4135519A1 (en) | 2020-04-16 | 2023-02-22 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
EP4135520A1 (en) | 2020-04-16 | 2023-02-22 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
AR122415A1 (es) | 2020-04-16 | 2022-09-07 | Bayer Ag | Combinaciones de compuestos activos y composiciones fungicidas que los comprenden |
WO2021209490A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Cyclaminephenylaminoquinolines as fungicides |
KR20230007398A (ko) | 2020-04-21 | 2023-01-12 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서 2-(헤트)아릴-치환된 축합 헤테로시클릭 유도체 |
EP4143167A1 (en) | 2020-04-28 | 2023-03-08 | Basf Se | Pesticidal compounds |
TW202208347A (zh) | 2020-05-06 | 2022-03-01 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之新穎雜芳基三唑化合物 |
EP4146628A1 (en) | 2020-05-06 | 2023-03-15 | Bayer Aktiengesellschaft | Pyridine (thio)amides as fungicidal compounds |
EP4149929A1 (en) | 2020-05-12 | 2023-03-22 | Bayer Aktiengesellschaft | Triazine and pyrimidine (thio)amides as fungicidal compounds |
EP3909950A1 (en) | 2020-05-13 | 2021-11-17 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
US20230192617A1 (en) | 2020-05-19 | 2023-06-22 | Bayer Cropscience Aktiengesellschaft | Azabicyclic(thio)amides as fungicidal compounds |
BR112022024394A2 (pt) | 2020-06-04 | 2023-01-31 | Bayer Ag | Heterociclil pirimidinas e triazinas como novos fungicidas |
CN116057056A (zh) | 2020-06-10 | 2023-05-02 | 拜耳公司 | 作为杀真菌剂的氮杂双环取代的杂环化合物 |
CN111689915A (zh) * | 2020-06-14 | 2020-09-22 | 湖南斯派克科技股份有限公司 | 1-(2,4-二氯苯基)-4-二氟甲基-3-甲基-1h-1,2,4-三唑-5-酮的制备方法 |
EP4168404A1 (en) | 2020-06-18 | 2023-04-26 | Bayer Aktiengesellschaft | 3-(pyridazin-4-yl)-5,6-dihydro-4h-1,2,4-oxadiazine derivatives as fungicides for crop protection |
UY39276A (es) | 2020-06-19 | 2022-01-31 | Bayer Ag | Uso de compuestos de 1,3,4–oxadiazol–2–ilpirimidina para controlar microorganismos fitopatógenos, métodos de uso y composiciones. |
UY39275A (es) | 2020-06-19 | 2022-01-31 | Bayer Ag | 1,3,4-oxadiazol pirimidinas como fungicidas, procesos e intermediarios para su preparación, métodos de uso y usos de los mismos |
WO2021255089A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazole pyrimidines and 1,3,4-oxadiazole pyridines as fungicides |
WO2021255091A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazoles and their derivatives as fungicides |
EP3929189A1 (en) | 2020-06-25 | 2021-12-29 | Bayer Animal Health GmbH | Novel heteroaryl-substituted pyrazine derivatives as pesticides |
WO2021260017A1 (en) | 2020-06-26 | 2021-12-30 | Bayer Aktiengesellschaft | Aqueous capsule suspension concentrates comprising biodegradable ester groups |
JP2023532548A (ja) | 2020-07-02 | 2023-07-28 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としてのヘテロサイクレン誘導体 |
WO2022033991A1 (de) | 2020-08-13 | 2022-02-17 | Bayer Aktiengesellschaft | 5-amino substituierte triazole als schädlingsbekämpfungsmittel |
WO2022053453A1 (de) | 2020-09-09 | 2022-03-17 | Bayer Aktiengesellschaft | Azolcarboxamide als schädlingsbekämpfungsmittel |
WO2022058327A1 (en) | 2020-09-15 | 2022-03-24 | Bayer Aktiengesellschaft | Substituted ureas and derivatives as new antifungal agents |
EP3974414A1 (de) | 2020-09-25 | 2022-03-30 | Bayer AG | 5-amino substituierte pyrazole und triazole als schädlingsbekämpfungsmittel |
EP3915371A1 (en) | 2020-11-04 | 2021-12-01 | Bayer AG | Active compound combinations and fungicide compositions comprising those |
EP3994989A1 (en) | 2020-11-08 | 2022-05-11 | Bayer AG | Agrochemical composition with improved drift, rainfastness and uptake properties |
EP3994986A1 (en) | 2020-11-08 | 2022-05-11 | Bayer Aktiengesellschaft | Agrochemical composition with improved drift and spreading properties |
EP3994988A1 (en) | 2020-11-08 | 2022-05-11 | Bayer AG | Agrochemical composition with improved drift, spreading and rainfastness properties |
EP3994991A1 (en) | 2020-11-08 | 2022-05-11 | Bayer Aktiengesellschaft | Agrochemical composition with improved drift, spreading, uptake and rainfastness properties |
EP3994985A1 (en) | 2020-11-08 | 2022-05-11 | Bayer Aktiengesellschaft | Agrochemical composition with improved drift properties |
EP3994994A1 (en) | 2020-11-08 | 2022-05-11 | Bayer Aktiengesellschaft | Low drift, rainfastness, high spreading, high uptake and ulv tank mix adjuvant formulation |
EP3994987A1 (en) | 2020-11-08 | 2022-05-11 | Bayer AG | Agrochemical composition with improved drift and uptake properties |
EP3994995A1 (en) | 2020-11-08 | 2022-05-11 | Bayer Aktiengesellschaft | Low drift, rainfastness, high spreading, high uptake and ulv tank mix adjuvant formulation |
EP3994990A1 (en) | 2020-11-08 | 2022-05-11 | Bayer AG | Agrochemical composition with improved drift, spreading and uptake properties |
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WO2024068519A1 (en) | 2022-09-28 | 2024-04-04 | Bayer Aktiengesellschaft | 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide |
WO2024068518A1 (en) | 2022-09-28 | 2024-04-04 | Bayer Aktiengesellschaft | 3-heteroaryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide |
EP4353082A1 (en) | 2022-10-14 | 2024-04-17 | Bayer Aktiengesellschaft | Herbicidal compositions |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3316300A1 (de) * | 1982-05-07 | 1983-11-24 | Kureha Kagaku Kogyo K.K., Tokyo | Heribizide zusammensetzung mit einem gehalt an einem derivat des 1,2,4-triazols als wirkstoff |
JPH01230562A (ja) | 1987-03-27 | 1989-09-14 | Kumiai Chem Ind Co Ltd | フェニルトリアゾール誘導体及び殺虫剤 |
JP2729810B2 (ja) | 1988-09-27 | 1998-03-18 | クミアイ化学工業株式会社 | フェニルトリアゾール誘導体及び殺虫剤 |
JPH0291062A (ja) * | 1988-09-27 | 1990-03-30 | Kumiai Chem Ind Co Ltd | トリアゾール誘導体及び殺虫剤 |
JPH07258227A (ja) * | 1994-03-25 | 1995-10-09 | Kumiai Chem Ind Co Ltd | フェニルトリアゾール誘導体及び殺虫剤 |
DE19548415A1 (de) * | 1995-12-22 | 1997-06-26 | Bayer Ag | 1-Aryl-3-halogenalkyl-5-arylaminotriazole |
GB2327418A (en) | 1997-07-18 | 1999-01-27 | Rhone Poulenc Agriculture | Derivatives of 2-benzoylcyclohexane-1,3-dione |
JP4209995B2 (ja) | 1998-04-27 | 2009-01-14 | クミアイ化学工業株式会社 | 3−アリールフェニルスルフィド誘導体及び殺虫、殺ダニ剤 |
DE69934224T2 (de) | 1998-04-27 | 2007-10-04 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenylsulfid-derivate und insektizide und mitizide |
JP2000239262A (ja) * | 1999-02-17 | 2000-09-05 | Sumitomo Chem Co Ltd | トリアゾール化合物およびその用途 |
ES2218230T3 (es) * | 1999-09-30 | 2004-11-16 | Basf Corporation | Resinas con funcionalidad carbamato de adhesion mejorada, procedimiento para su preparacion y metodo para mejorar la adhesion entre capas. |
US7146433B2 (en) * | 2002-02-01 | 2006-12-05 | Lenovo Singapore Pte. Ltd | Extending an allowable transmission distance between a wireless device and an access point by communication with intermediate wireless devices |
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US7872036B2 (en) | 2011-01-18 |
MX2007004710A (es) | 2007-06-14 |
WO2006043635A1 (ja) | 2006-04-27 |
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UA86251C2 (uk) | 2009-04-10 |
RU2007118700A (ru) | 2008-11-27 |
TWI382020B (zh) | 2013-01-11 |
EP1803712A4 (en) | 2009-08-26 |
JPWO2006043635A1 (ja) | 2008-05-22 |
IL182594A (en) | 2013-04-30 |
BRPI0516976B1 (pt) | 2014-07-22 |
ZA200702684B (en) | 2008-08-27 |
CA2581725A1 (en) | 2006-04-27 |
IL182594A0 (en) | 2007-07-24 |
TW200630349A (en) | 2006-09-01 |
RU2394819C2 (ru) | 2010-07-20 |
BRPI0516976B8 (pt) | 2016-05-24 |
CN101039922B (zh) | 2011-04-13 |
CN101039922A (zh) | 2007-09-19 |
KR101310073B1 (ko) | 2013-09-24 |
EP1803712B1 (en) | 2015-12-30 |
BRPI0516976A (pt) | 2008-09-30 |
NZ553200A (en) | 2009-09-25 |
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