TWI662035B - 殺蟲組成物及相關方法 - Google Patents
殺蟲組成物及相關方法 Download PDFInfo
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- TWI662035B TWI662035B TW104115573A TW104115573A TWI662035B TW I662035 B TWI662035 B TW I662035B TW 104115573 A TW104115573 A TW 104115573A TW 104115573 A TW104115573 A TW 104115573A TW I662035 B TWI662035 B TW I662035B
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- TW
- Taiwan
- Prior art keywords
- methyl
- alkyl
- salt
- sodium
- ethyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 115
- 238000000034 method Methods 0.000 title abstract description 28
- 230000000361 pesticidal effect Effects 0.000 title description 10
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 239000002917 insecticide Substances 0.000 claims abstract description 30
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 12
- 230000002013 molluscicidal effect Effects 0.000 claims abstract description 7
- -1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 434
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 239000011734 sodium Substances 0.000 claims description 38
- 229910052708 sodium Inorganic materials 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 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 claims description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 159000000000 sodium salts Chemical class 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 17
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 239000011591 potassium Substances 0.000 claims description 16
- 229910052700 potassium Inorganic materials 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 244000025254 Cannabis sativa Species 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 230000002363 herbicidal effect Effects 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- 239000004009 herbicide Substances 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 235000021307 Triticum Nutrition 0.000 claims description 8
- 241000209140 Triticum Species 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 8
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 8
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 235000013399 edible fruits Nutrition 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000005871 repellent Substances 0.000 claims description 7
- 230000002940 repellent Effects 0.000 claims description 7
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical class CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 6
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 6
- 239000005561 Glufosinate Substances 0.000 claims description 6
- 239000005574 MCPA Substances 0.000 claims description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 6
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 claims description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229920001296 polysiloxane Polymers 0.000 claims description 6
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 6
- 230000002195 synergetic effect Effects 0.000 claims description 6
- OTKXWJHPGBRXCR-UHFFFAOYSA-N (2-chloro-4-nitrophenoxy)-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1Cl OTKXWJHPGBRXCR-UHFFFAOYSA-N 0.000 claims description 5
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 claims description 5
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 5
- 239000005946 Cypermethrin Substances 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 241000257159 Musca domestica Species 0.000 claims description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 239000005626 Tribenuron Substances 0.000 claims description 5
- 159000000007 calcium salts Chemical class 0.000 claims description 5
- 239000006013 carbendazim Substances 0.000 claims description 5
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 claims description 5
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 claims description 5
- 229960005424 cypermethrin Drugs 0.000 claims description 5
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 claims description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
- 229960002125 enilconazole Drugs 0.000 claims description 5
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 239000005077 polysulfide Substances 0.000 claims description 5
- 229920001021 polysulfide Polymers 0.000 claims description 5
- 150000008117 polysulfides Polymers 0.000 claims description 5
- 239000010902 straw Substances 0.000 claims description 5
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 claims description 5
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 claims description 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 4
- DSVOTYIOPGIVPP-UHFFFAOYSA-N (3,4-dichlorophenyl)methyl n-methylcarbamate Chemical compound CNC(=O)OCC1=CC=C(Cl)C(Cl)=C1 DSVOTYIOPGIVPP-UHFFFAOYSA-N 0.000 claims description 4
- RLLPVAHGXHCWKJ-MJGOQNOKSA-N (3-phenoxyphenyl)methyl (1r,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-MJGOQNOKSA-N 0.000 claims description 4
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 claims description 4
- ATKFMEGWDYLXBP-UHFFFAOYSA-N 2-(2,4,5-trichlorophenoxy)ethanol Chemical compound OCCOC1=CC(Cl)=C(Cl)C=C1Cl ATKFMEGWDYLXBP-UHFFFAOYSA-N 0.000 claims description 4
- KQUYPOJCTWSLSE-UHFFFAOYSA-N 2-[4-[1-[2-(diethylamino)-2-oxoethyl]pyridin-1-ium-4-yl]pyridin-1-ium-1-yl]-n,n-diethylacetamide Chemical compound C1=C[N+](CC(=O)N(CC)CC)=CC=C1C1=CC=[N+](CC(=O)N(CC)CC)C=C1 KQUYPOJCTWSLSE-UHFFFAOYSA-N 0.000 claims description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 4
- LITHUQSNACPLIL-UHFFFAOYSA-N 2-butan-2-yl-4,6-dinitrophenol;2-(2-hydroxyethylamino)ethanol Chemical compound OCCNCCO.CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LITHUQSNACPLIL-UHFFFAOYSA-N 0.000 claims description 4
- GLDWASBMYWLQGG-UHFFFAOYSA-N 2-butoxyethyl 2-(2,4,5-trichlorophenoxy)acetate Chemical compound CCCCOCCOC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl GLDWASBMYWLQGG-UHFFFAOYSA-N 0.000 claims description 4
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 4
- QQRJUWIHLNBDQF-UHFFFAOYSA-N 6-chloro-5-methylsulfanylpyrimidine-2,4-diamine Chemical compound CSC1=C(N)N=C(N)N=C1Cl QQRJUWIHLNBDQF-UHFFFAOYSA-N 0.000 claims description 4
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- 229940127437 Chloride Channel Antagonists Drugs 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000005944 Chlorpyrifos Substances 0.000 claims description 4
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005644 Dazomet Substances 0.000 claims description 4
- 239000005947 Dimethoate Substances 0.000 claims description 4
- 239000005630 Diquat Substances 0.000 claims description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005558 Fluroxypyr Substances 0.000 claims description 4
- 239000005562 Glyphosate Substances 0.000 claims description 4
- RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002169 Metam Substances 0.000 claims description 4
- CVRALZAYCYJELZ-UHFFFAOYSA-N O-(4-bromo-2,5-dichlorophenyl) O-methyl phenylphosphonothioate Chemical compound C=1C=CC=CC=1P(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl CVRALZAYCYJELZ-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 4
- QOHVLZBCVSJGFV-UHFFFAOYSA-N azane;2-methyl-4,6-dinitrophenol Chemical compound [NH4+].CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1[O-] QOHVLZBCVSJGFV-UHFFFAOYSA-N 0.000 claims description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 4
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 4
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 4
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 claims description 4
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 4
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 4
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 claims description 4
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- JUCNGUOYQGHBJC-UHFFFAOYSA-N methyl 2-(2,4,5-trichlorophenoxy)acetate Chemical compound COC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl JUCNGUOYQGHBJC-UHFFFAOYSA-N 0.000 claims description 2
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- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 claims description 2
- LYPWWQLKWQNQKV-UHFFFAOYSA-N methyl 2-[5-ethyl-2-[[4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(CC)=CC=C1COC1=CC=C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)C=C1 LYPWWQLKWQNQKV-UHFFFAOYSA-N 0.000 claims description 2
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- KBHDSWIXRODKSZ-UHFFFAOYSA-N methyl 5-chloro-2-(trifluoromethylsulfonylamino)benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C(F)(F)F KBHDSWIXRODKSZ-UHFFFAOYSA-N 0.000 claims description 2
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 claims description 2
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 claims description 2
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- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims 1
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- JRPGMCRJPQJYPE-UHFFFAOYSA-N zinc;carbanide Chemical compound [CH3-].[CH3-].[Zn+2] JRPGMCRJPQJYPE-UHFFFAOYSA-N 0.000 description 1
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Abstract
此揭示係有關於下列領域:具有抗節肢動物門、軟體動物門及/或圓形動物門之害蟲之殺蟲效果的分子、生產此等分子之方法、用於此方法之中間產物、含有此等分子之殺蟲組成物,以及使用此等殺蟲組成物抗此等害蟲之方法。此等殺蟲組成物可使用作為,例如,殺蜱蟎劑、殺昆蟲劑、殺蟎劑、殺軟體動物劑及/或殺線蟲劑。此文件揭示具有下列式I之分子,或其任一農業上可接受的鹽類,其中R1、R2、R3、R4、R5、R6、R7、R8、R9、X1、Q及n係如本文中所述。
Description
此申請案主張2015年5月16日提申之美國專利臨時申請案第61/994,660號,“PESTICIDAL COMPOSITIONS AND RELATED METHODS”,之利益。
此揭示係有關於下列領域:具有抗節肢動物門、軟體動物門及/或圓形動物門之害蟲之殺蟲效果的分子、生產此等分子之方法、用於此方法之中間產物、含有此等分子之殺蟲組成物,以及使用此等殺蟲組成物抗此等害蟲之方法。此等殺蟲組成物可使用作為,例如,殺蜱蟎劑、殺昆蟲劑、殺蟎劑、殺軟體動物劑(molluscicide)及/或殺線蟲劑。
控制害蟲族群對於人類健康、現代農業、食物貯存以及衛生是至關重要的。有超過一萬個物種的害蟲會導致農業損失,而每年全球農業損失數量達數十億美元。因此,對於新的殺蟲劑以及產生與使用此等殺蟲劑之方法一
直有需求。
本發明係關於一種殺蟲組成物,其包含式I的化合物或其任一農業上可接受的鹽類:
其中:(a)R 1 、R 2 及R 3 各自獨立地選自於下列所構成的群組:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基、C3-C6環烷基、芳基、經取代的芳基、C1-C4烷基苯基、苯基、經取代的苯基、雜環基,以及經取代的雜環基,(b)其中各個該R1、R2及R3,當被取代時,具有一個或更多個獨立地選自於下列所構成的群組之取代基:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基,及C3-C6環烷基;(c)R 4 、R 5 、R 6 、R 7 及R 8 各自獨立地選自於下列所構成的群組:H、F、Cl、Br、CN、OH、C1-C4烷基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基,及C3-C6
環烷基
(d)R 9 係選自於下列所構成的群組:H、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、(C1-C4烷基)(C3-C6環烷基)、C1-C4烷基苯基、C1-C4鹵烷基苯基、芳基、經取代的芳基、苯基、吡啶基(pyridiyl)、嘧啶基、經取代的苯基、經取代的吡啶基、(C1-C4烷基)C(=O)(苯基)、(C1-C4烷基)(鹵烷基)(苯基)、(C1-C4烷基)(鹵烷基)(烷基)、(C1-C4烷基)C(=O)O(C1-C4烷基)、(C1-C4烷基)C(=NOR10)R11、C(=O)(C1-C4烷基)S(=O)m(C1-C4烷基)、(C1-C4烷基)S(=O)m(C1-C4烷基)、(C1-C4烷基)S(=O)m(C1-C4鹵烷基)、C(=O)R13,及(C1-C4烷基)C(=O)N(RxRy),其中R9,當被取代時,具有一個或更多個獨立地選自於下列所構成的群組之取代基:F、Cl、CN、OH、C1-C4鹵烷基、C1-C4鹵烷氧基,及C1-C4烷氧基、嘧啶基,或是其中R x 及R y 一起形成一個6員飽和環狀基團或是一個含有一個氮雜原子之6員飽和環狀基團,且其中該環狀基團當被取代時,具有一個或更多個獨立地選自於下列所構成的群組之取代基:C1-C4烷基、C3-C6環烷基,及苯基;(e)R 10 及R 11 各自獨立地選自於下列所構成的群組:H、Cl、C1-C4烷基、C1-C4鹵烷基、C1-C4烷基苯基、苯基,及經取代的苯基、芳基、經取代的芳基,其中R 10 及R 11 ,當被取代時,具有一個或更多個獨
立地選自於H或C1-C4鹵烷基之取代基;(f)R 13 係選自於下列所構成的群組:H、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、(C1-C4烷基)(C3-C6環烷基)、C1-C4烷基苯基、C1-C4鹵烷基苯基、苯基、吡啶基(pyridiyl)、嘧啶基、經取代的苯基、經取代的吡啶基、芳基、經取代的芳基、(C1-C4烷基)C(=O)(苯基)、(C1-C4烷基)(鹵烷基)(苯基)、(C1-C4烷基)(鹵烷基)(烷基)、(C1-C4烷基)C(=O)O(C1-C4烷基)、(C1-C4烷基)C(=NOR10)R11、C(=O)(C1-C4烷基)S(=O)m(C1-C4烷基)、(C1-C4烷基)S(=O)m(C1-C4烷基),及(C1-C4烷基)S(=O)m(C1-C4鹵烷基);(g)X 1 為N或CR12,其中R 12 係選自於下列所構成的群組:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基、C3-C6環烷基、C1-C4烷基苯基、芳基、經取代的芳基、苯基、經取代的苯基、雜芳基,及經取代的雜芳基,以及其中R 12 ,當被取代時,具有一個或更多個獨立地選自於下列所構成的群組之取代基:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基,及C3-C6環烷基;(h)Q為O(氧),或S(硫);(i)n為0、1,或2;以及(j)m為0、1,或2。
在此等定義中所提供之範例一般並非非窮舉性的,及不得解釋為限制本揭示。應理解,取代基應依從與其所連接的特定分子相關之化學鍵結規則及立體相容性的限制。
「烷基」係指且包括一個非環狀、飽和的分支或是不分支烴類。非限制性實例可包括甲基、乙基、丙基、異丙基、1-丁基、2-丁基、異丁基、三級丁基、戊基、2-甲基丁基、1,1-二甲基丙基、己基、庚基、辛基、壬基,或是癸基。
「環烷基」係指且包括單環或多環的飽和烴類。非限制性實例可包括環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環癸基、降基、雙環[2.2.2]辛基,或是十氫萘基(decahydronapthyl)。
「烯基」係指且包括非環狀的、分支或不分支的烴類,其含有至少一個碳-碳雙鍵。非限制性實例可包括乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基,或癸烯基。
「環烯基」係指且包括單環或多環的烴類,其含有至少一個碳-碳雙鍵。非限制性實例可包括環戊烯基、
環己烯基、環庚烯基、環辛烯基,或環癸烯基。
「炔基」係指且包括非環狀的、分支或不分支的
烴類,其含有至少一個碳-碳參鍵。非限制性實例可包括乙炔基、炔丙基、丁炔基、戊炔基、己炔基、庚炔基、辛炔基、壬炔基,或癸炔基。
「環炔基」係指且包括單環或多環的烴類,其含
有至少一個碳-碳參鍵。非限制性實例可包括環庚炔基、環辛炔基,或環癸炔基。
「芳基」係指且包括帶有或不帶有任何取代基之
芳香族化合物,以及可以包括或可以不包括一個或更多個雜原子。非限制性實例可包括苯基、萘基或吡啶基。
「烷氧基」係指且包括一種含有至少一個碳-氧
單鍵之烷基。非限制性實例可包括甲氧基、乙氧基、丙氧基、丁氧基、環丙氧基、環丁氧基或環戊氧基。
「烯氧基」係指且包括一種含有至少一個碳-氧
單鍵之烯基。非限制性實例可包括烯丙氧基、丁烯氧基、戊烯氧基、己烯氧基、庚烯氧基、辛烯氧基、壬烯氧基,或癸烯氧基。
「炔氧基」係指且包括一種含有至少一個碳-氧
單鍵之炔基。非限制性實例可包括戊炔氧基、己炔氧基、庚炔氧基、辛炔氧基、壬炔氧基,或癸炔氧基。
「環烷氧基」係指且包括一種含有至少一個碳-
氧單鍵之環烷基。非限制性實例可包括環丙氧基、環丁氧基、環戊氧基、環己氧基、環庚氧基、環辛氧基、環癸氧
基、降基氧基,或雙環[2.2.2]辛基氧基。
「環鹵烷基」係指且包括一種單環或多環的飽和
取代基,其含有碳、鹵素和氫。非限制性實例可包括1-氯環丙基、1-氯環丁基,或是1-二氯環戊基。
「環烯氧基」係指且包括一種進一步由碳-氧單
鍵組成之環烯基。非限制性實例可包括環丁烯氧基、環戊烯氧基、環己烯氧基、環庚烯氧基、環辛烯氧基、環癸烯氧基、降烯基氧基,或是雙環[2.2.2]辛烯基氧基。
「烷基硫基」係指且包括一種含有至少一個碳-
硫單鍵之烷基。
「鹵烷基硫基」係指且包括一種烷基,其含有至
少一個碳-硫單鍵及鹵素原子。
「鹵基」或「鹵素」係指且包括氟、氯、溴,或
是碘。
「鹵烷基」係指且包括以至少一個鹵素原子取代
的烷基。
「鹵烷氧基」係指且包括以至少一個鹵素原子取
代的烷氧基。
「雜原子」係指且包括硫(S)、氧(O),或氮(N)
原子。
「雜烷基」係指且包括一種含有至少一個硫
(S)、氧(O),或氮(N)原子之烷基。
「雜環基」係指且包括一種環狀取代基,其可為
完全飽和、部分不飽和或完全不飽和的,其中該環狀結構
含有至少一個碳及至少一個雜原子,其中該雜原子為氮、硫或氧。就硫而言,該原子可處於其他氧化態,諸如亞碸及碸。芳香族雜環基之實例包括,但是不限於苯并呋喃基、苯并異噻唑基、苯并異噁唑基、苯并噁唑基、苯并噻吩基、苯并噻唑基、啉基(cinnolinyl)、呋喃基、咪唑基、吲唑基、吲哚基、異吲哚基、異喹啉基、異噻唑基、異唑基、二唑基、唑啉基、唑基、呔基、吡基、吡唑啉基、吡唑基、嗒基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹喏啉基、四唑基、噻唑啉基、噻唑基、噻吩基、三基及三唑基。完全飽和之雜環基之實例包括,但不限於六氫吡基、哌啶基、嗎啉基、吡咯啶基、氧雜環丁基、四氫呋喃基、四氫噻吩基,以及四氫哌喃基。部分不飽和的雜環基之實例包括,但是不限於1,2,3,4-四氫喹啉基、4,5-二氫-唑基、4,5-二氫-1H-吡唑基、4,5-二氫-異唑基以及2,3-二氫-[1,3,4]-二唑基。其他實例包括以下各者:
硫化三亞甲基 硫化三亞甲基-氧化物 硫化三亞甲基-二氧化物。
「殺蟲有效量」意指且包括,會對至少一種昆蟲引起不良反應之活性材料的量,其中該不良反應可包括偏離自然的發展、殺死、調節等等。
「控制」或其文法上之變化,意指且包括,調節
活昆蟲之數目或調節昆蟲之可存活卵之數目,或是二者。
「協同性作用」或其文法上之變化,意指且包
括,二種或多種活性製劑結合時產生之合作作用,其中該二種或多種活性製劑之結合活性,超過各單獨活性製劑之活性的總合。
在一特定具體例中,一種殺蟲組成物包含式I的化合物,或其任一農業上可接受的鹽類:
其中:R 1 、R 2 及R 3 各自獨立地選自於下列所構成的群組:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基、C3-C6環烷基、芳基、經取代的芳基、C1-C4烷基苯基、苯基、經取代的苯基、雜環基,及經取代的雜環基,其中各個烷基、烯基、鹵烷基、烷氧基、鹵烷氧基、環烷基、芳基、烷基苯基、苯基,以及雜環係選擇性地以一個或更多個獨立地選自於下列所構成的群組之取代基予以取代:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷
基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基,以及C3-C6環烷基;R 4 、R 5 、R 6 、R 7 及R 8 各自獨立地選自於下列所構成的群組:H、F、Cl、Br、CN、OH、C1-C4烷基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基,及C3-C6環烷基;R 9 係選自於下列所構成的群組:H、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、(C1-C4烷基)(C3-C6環烷基)、C1-C4烷基苯基、C1-C4鹵烷基苯基、芳基、經取代的芳基、苯基、吡啶基(pyridiyl)、嘧啶基、經取代的苯基、經取代的吡啶基、(C1-C4烷基)C(=O)(苯基)、(C1-C4烷基)(鹵烷基)(苯基)、(C1-C4烷基)(鹵烷基)(烷基)、(C1-C4烷基)C(=O)O(C1-C4烷基)、(C1-C4烷基)C(=NOR10)R11、C(=O)(C1-C4烷基)S(=O)m(C1-C4烷基)、(C1-C4烷基)S(=O)m(C1-C4烷基)、(C1-C4烷基)S(=O)m(C1-C4鹵烷基)、(C1-C4烷基)C(=O)N(RxRy),以及C(=O)R13,其中各個烷基、經取代的芳基、經取代的苯基,及經取代的吡啶基係選擇性地以一個或更多個獨立地選自於下列所構成的群組之取代基予以取代:F、Cl、CN、OH、C1-C4鹵烷基、C1-C4鹵烷氧基,及C1-C4烷氧基、嘧啶基,或是其中R x 及R y 一起形成一個6員飽和環狀基團,其選擇性地含有一個額外的氮雜原子,且其中該環狀基團可以一個或更多個獨立地選自於下列所構成的群組之取代基予以取代:C1-C4烷基、C3-C6環烷基,及苯基;
R 10 及R 11 各自獨立地選自於下列所構成的群組:H、Cl、C1-C4烷基、C1-C4鹵烷基、C1-C4烷基苯基、苯基,及經取代的苯基、芳基、經取代的芳基,其中各個烷基、鹵烷基、烷基苯基、經取代的芳基,及經取代的苯基係選擇性地以一個或更多個獨立地選自於H或C1-C4鹵烷基之取代基予以取代;R 13 係選自於下列所構成的群組:H、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、(C1-C4烷基)(C3-C6環烷基)、C1-C4烷基苯基、C1-C4鹵烷基苯基、苯基、吡啶基(pyridiyl)、嘧啶基、經取代的苯基、經取代的吡啶基、芳基、經取代的芳基、(C1-C4烷基)C(=O)(苯基)、(C1-C4烷基)(鹵烷基)(苯基)、(C1-C4烷基)(鹵烷基)(烷基)、(C1-C4烷基)C(=O)O(C1-C4烷基)、(C1-C4烷基)C(=NOR10)R11、C(=O)(C1-C4烷基)S(=O)m(C1-C4烷基)、(C1-C4烷基)S(=O)m(C1-C4烷基),及(C1-C4烷基)S(=O)m(C1-C4鹵烷基);X 1 為N或CR12,其中R 12 係選自於下列所構成的群組:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基、C3-C6環烷基、C1-C4烷基苯基、芳基、經取代的芳基、苯基、經取代的苯基、雜芳基,及經取代的雜芳基,以及其中各個烷基、烯基、鹵烷基、烷氧基、鹵烷氧基、環烷基、烷基苯基、苯基、芳基,及雜芳基係選擇性地以一個或更多個獨立地選自於下列所構成的群組之取代基予
以取代:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基,以及C3-C6環烷基;Q為O(氧),或S(硫);n為0、1,或2;以及m為0、1,或2。
在一些具體例中,該殺蟲組成物可包含一種式I的化合物或其任一農業上可接受的鹽類,其中n為0且Q為氧,如同顯示於以下之式I-A的吡唑并[3,4-c]哌啶-2-酮(pyrazolo[3,4-c]piperidin-2-one)化合物:
在一具體例中,該式I-A的吡唑并[3,4-c]哌啶-2-酮(pyrazolo[3,4-c]piperidin-2-one)化合物可以如同流程圖1中所示予以製備。
一種肼化合物1-1,其中R1、R2、R3及X1係如先前所定義,且y可以為0、1,或2,在鹼諸如乙酸鈉,及溶劑混合物諸如乙醇和水存在下,於大約室溫中,可以與哌啶二酮化合物1-2反應,其中R5、R6、R7、R8及R9係如先前所定義,以提供一種肼化合物1-3(A,流程圖1)。
該肼化合物1-3環化成吡唑[3,4-c]哌啶二酮(pyrazole[3,4-c]piperidinone)化合物I-A,其中R4係如先前所定義,可以於溫度範圍由大約50℃至大約90℃之下,在純淨的或配於像是N,N-二甲基甲醯胺之溶劑內,於例如為N,N-二甲基甲醯胺‧二甲縮醛(R4=H)之製劑存在下發生(B,流程圖1)。
在一特定的具體例中,式I-A的吡唑并[3,4-c]哌啶-2-酮化合物可以如同流程圖2中所示予以製備。
哌啶二酮化合物1-2,其中R5、R6、R7、R8及R9係如先前所定義,轉化成中間物化合物2-1,其中R4係如先前所定義,可以在溫度範圍由大約50℃至大約90℃之下,於像是N,N-二甲基甲醯胺之極性非質子性溶劑內,在例如為N,N-二甲基甲醯胺‧二甲縮醛(R4=H)之製劑存在下
完成(A,流程圖2)。
中間物化合物2-1,可以在溫度範圍由大約50℃至大約回流之下,於像是乙醇之極性質子性溶劑內,與一種肼化合物,諸如水合肼(hydrazine‧hydrate)反應以提供一種吡唑并[3,4-c]哌啶-2-酮化合物2-2(B,流程圖2)。
一旦吡唑并[3,4-c]哌啶-2-酮化合物2-2在溫度範圍由大約80℃至大約120℃下,於像是N,N-二甲基甲醯胺之極性非質子性溶劑內,與一種芳基鹵化物反應,諸如3-氟吡啶,則可以獲得吡唑并[3,4-c]哌啶-2-酮化合物I-A,其中R1、R2、R3及X1係如先前所定義(C,流程圖2)。
在一些具體例中,該殺蟲組成物可包含式I-A的吡唑并[3,4-c]哌啶-2-酮化合物或其任一農業上可接受的鹽類,其中R1、R2、R3、R4、R5、R6、R7、R8、R9及X1係如
先前所定義但R9不是氫(H)。
於其他的具體例中,此式I-A的吡唑并[3,4-c]哌
啶-2-酮化合物,其中R1、R2、R3、R4、R5、R6、R7、R8、R9及X1係如先前所定義但R9不是H,可以如同流程圖3中所示予以製備。可以藉由將吡唑并[3,4-c]哌啶-2-酮化合物3-1,其中R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,予以烷化來製備吡唑并[3,4-c]哌啶-2-酮化合物3-2,其中R9係如先前所定義但不是H。
作為非限制性實例,該吡唑并[3,4-c]哌啶-2-酮
化合物3-1可以在溫度範圍由大約0℃至大約室溫之下,於像是四氫呋喃或N,N-二甲基甲醯胺之極性非質子性溶劑內,在一種鹼諸如氫化鈉存在下,與一種烷基鹵化物,諸如碘甲烷,進行反應以提供吡唑并[3,4-c]哌啶-2-酮化合物3-2(A,流程圖3)。
作為另一個非限制性實例,該吡唑并[3,4-c]哌
啶-2-酮化合物3-1可以在大概室溫下,於像是N,N-二甲基甲醯胺之極性非質子性溶劑內,在一種鹼諸如氫氧化鈉存在下,與一種烷基鹵化物,諸如環丙基溴甲烷,進行反應
以提供吡唑并[3,4-c]哌啶-2-酮化合物3-2(B,流程圖3)。
作為再另一個非限制性實例,該吡唑并[3,4-c]
哌啶-2-酮化合物3-1可以在大概室溫下,於像是N,N-二甲基甲醯胺之極性非質子性溶劑內,在一種鹼諸如雙(三甲矽)醯胺化鋰存在下,與一種烷基鹵化物,諸如1-(溴甲基)-4-氟苯,進行反應以提供吡唑并[3,4-c]哌啶-2-酮化合物3-2(C,流程圖3)。
作為另外的非限制性實例,該吡唑并[3,4-c]哌
啶-2-酮化合物3-1可以在大概室溫下,於像是N,N-二甲基甲醯胺之極性非質子性溶劑內,在一種鹼諸如雙(三甲矽)醯胺化鋰存在下,及諸如六甲基磷酸三胺之添加劑存在下,可以與一種烷基鹵化物,諸如2-氯乙酸乙酯,進行反應以提供吡唑并[3,4-c]哌啶-2-酮化合物3-2(D,流程圖3)。
在一些具體例中,此式I-A的吡唑并[3,4-c]哌啶
-2-酮化合物,其中R1、R2、R3、R4、R5、R6、R7、R8、R9及X1係如先前所定義但R9不是H,可以如同流程圖4中所示予以製備。可以藉由將吡唑并[3,4-c]哌啶-2-酮化合物3-1,予以芳基化來製備吡唑并[3,4-c]哌啶-2-酮化合物3-2,其中R9係如先前所定義但不是H。
作為非限制性實例,吡唑并[3,4-c]哌啶-2-酮化
合物3-1可以於範圍由大約70℃至大約回流的溫度下,在像是1,4-二噁烷之極性非質子性溶劑內,於存在一種催化劑諸如碘化銅(I)、一種配位基諸如反式-1,2-二胺基環己烷,及一種鹼諸如碳酸銫的情況下,與一種芳基鹵化物,諸如2-溴吡啶,進行反應以提供吡唑并[3,4-c]哌啶-2-酮化合物3-2(A,流程圖4)。
作為另一個非限制性實例,吡唑并[3,4-c]哌啶
-2-酮化合物3-1可以於範圍由大約70℃至大約回流的溫度下,在像是1,4-二噁烷之極性非質子性溶劑內,於存在一種催化劑諸如三(二亞苄基丙酮)二鈀(0)、一種配位基諸如4,5-雙(二苯膦)-9,9-二甲基(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene),及一種鹼諸如碳酸銫的情況下,與一種芳基鹵化物,諸如2-溴-5-(三氟甲基)吡啶,進行反應以提供吡唑并[3,4-c]哌啶-2-酮化合物3-2(B,流程圖4)。
在特定的具體例中,該殺蟲組成物可包含式I-A
的吡唑并[3,4-c]哌啶-2-酮化合物或其任一農業上可接受的鹽類,其中R9為C(=O)R13,以及R1、R2、R3、R4、R5、
R6、R7、R8、R13及X1係如先前所定義。
在一個具體例中,此式I-A的吡唑并[3,4-c]哌啶
-2-酮化合物,其中R9為C(=O)R13且R13為(C1-C4烷基)S(=O)m(C1-C4烷基),可以如同流程圖5中所示予以製備。
如同流程圖5中所示,吡唑并[3,4-c]哌啶-2-酮化
合物3-1,其中R1、R2、R3、R4、R5、R6、R7、R8以及X1係如先前所定義,可以在溫度範圍由大約80℃至大約120℃之下微波加熱,於像是1,2-二氯乙烷之極性非質子性溶劑內,在一種鹼諸如N-乙基-N-異丙基丙-2-胺存在下,用一種醯化劑諸如3-(甲硫基)丙醯氯,予以醯化以提供吡唑并[3,4-c]哌啶-2-酮化合物5-1,其中R13為(C1-C4烷基)S(=O)m(C1-C4烷基)。
在一些具體例中,該殺蟲組成物可包含式I-A的
吡唑并[3,4-c]哌啶-2-酮化合物或其任一農業上可接受的鹽類,其中當m為0時,R9為(C1-C4烷基)S(=O)m(C1-C4烷基)或(C1-C4烷基)S(=O)m(C1-C4鹵烷基),以及R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義。
在另一個具體例中,此吡唑并[3,4-c]哌啶-2-酮
化合物I-A,其中當m為0時,R9為(C1-C4烷基)S(=O)m(C1-C4烷基)或(C1-C4烷基)S(=O)m(C1-C4鹵烷基),可以如同流程圖6中所示予以製備。
吡唑并[3,4-c]哌啶-2-酮酯化合物6-1,其中R1、
R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,在大概室溫下,於像是乙醇之極性質子性溶劑內,藉由一種諸如硼氫化鈉之還原劑,予以還原可以提供一種吡唑并[3,4-c]哌啶-2-酮醇化合物6-2(A,流程圖6)。
該吡唑并[3,4-c]哌啶-2-酮醇化合物6-2接而可以
在大概室溫下,於像是二氯甲烷之溶劑內,在存在一種鹼諸如三乙胺,及催化劑諸如4-二甲胺吡啶的情況下,藉由與一種鹵化劑諸如4-甲苯磺醯氯,進行反應而轉化成對應的吡唑并[3,4-c]哌啶-2-酮鹵化物化合物6-3(B,流程圖6)。
應該瞭解到本技藝已知的其他鹵化試劑,例如亞硫醯氯或三溴化磷,亦可以使用於此目的。
然後,吡唑并[3,4-c]哌啶-2-酮鹵化物化合物6-3
可以在大概室溫至大約100℃的溫度下,於諸如乙腈或N,N-二甲基甲醯胺之極性溶劑內,在一種鹼諸如存在下,諸如碳酸銫或甲氧鈉,與一種硫醇或鹵硫醇(halothiol)化合物,例如丙-1-硫醇或3,3,3-三氟丙-1-硫醇,進行反應以提供吡唑并[3,4-c]哌啶-2-酮硫化物化合物6-4(C,流程圖6)。
任擇地,吡唑并[3,4-c]哌啶-2-酮鹵化物化合物
6-3可以在大概室溫下,於像是乙腈之溶劑內,藉由與一種硫醇化(thiolate)劑諸如甲硫醇鈉,進行反應而轉化成吡唑并[3,4-c]哌啶-2-酮硫化物化合物6-4(D,流程圖6)。
在一些具體例中,該吡唑并[3,4-c]哌啶-2-酮鹵
化物化合物6-3,可以如同流程圖7中所示予以製備。
在一個具體例中,吡唑并[3,4-c]哌啶-2-酮化合
物3-1,其中R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以在大概室溫下,於含水甲醛存在下完成烷化作用,以提供吡唑并[3,4-c]哌啶-2-酮醇化合物6-2(A,流程圖7)。接而,該吡唑并[3,4-c]哌啶-2-酮醇化合物6-2可以在大概0℃至大約室溫的溫度下,於像是N,N-二甲基甲醯胺之溶劑存在下,與一種鹵化劑諸如亞硫醯氯進行反應,以提供吡唑并[3,4-c]哌啶-2-酮鹵化物化合物6-3(B,流程圖7)。應該瞭解到本技藝已知的其他鹵化試劑,例如三溴化磷,亦可以使用於此目的。
任擇地,在另一個具體例中,可以在大概室溫
至大約80℃的溫度下,於純淨的鹵化劑像是氯三甲矽烷內,藉由使吡唑并[3,4-c]哌啶-2-酮化合物3-1,與聚甲醛進行反應而直接獲得吡唑并[3,4-c]哌啶-2-酮鹵化物化合物6-3(C,流程圖7)。
在一個具體例中,吡唑并[3,4-c]哌啶-2-酮化合
物I-A,其中當m為0時,R9為(C1-C4烷基)S(=O)m(C1-C4烷基)或(C1-C4烷基)S(=O)m(C1-C4鹵烷基),可以如同流程圖8A中所示予以製備。
吡唑并[3,4-c]哌啶-2-酮鹵化物化合物6-3,其中
R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,之硫醇化可以藉由用硫乙酸來處理吡唑并[3,4-c]哌啶-2-酮鹵化物化合物6-3來完成,以提供吡唑并[3,4-c]哌啶-2-酮硫酯化合物8-1(A,流程圖8A)。
移除醯基以去保護吡唑并[3,4-c]哌啶-2-酮硫酯
化合物8-1上的硫醇基,接著使生成的吡唑并[3,4-c]哌啶-2-酮硫醇直接烷基化,可以在大概0℃至大約65℃的溫度下,於例如甲醇之溶劑中,藉由用一種鹼諸如碳酸鉀或氫氧化鈉,來處理化合物8-1而完成。繼而,使生成的硫醇化合物與一種烷化試劑反應,諸如(C1-C4烷基)鹵化物、(C1-C4烷基)三氟甲磺酸,或是(C1-C4鹵烷基)三氟甲磺酸,以提供吡唑并[3,4-c]哌啶-2-酮硫化物化合物6-4(B,流程圖8A)。
在一個具體例中,吡唑并[3,4-c]哌啶-2-酮化合
物I-A,其中當m為0時,R9為(C1-C4烷基)S(=O)m(C1-C4烷基)或(C1-C4烷基)S(=O)m(C1-C4鹵烷基),可以如同流程圖8B中所示予以製備。
吡唑并[3,4-c]哌啶-2-酮鹵化物化合物6-3可以與
硫乙酸反應,以提供吡唑并[3,4-c]哌啶-2-酮硫酯化合物8-1(A,流程圖8B)。
吡唑并[3,4-c]哌啶-2-酮硫酯化合物8-1接而可以
用一種胺鹼諸如吡咯啶,來處理以去保護硫醇基,以及提供吡唑并[3,4-c]哌啶-2-酮硫醇化合物8-2(C,流程圖8B)。
繼而,吡唑并[3,4-c]哌啶-2-酮硫醇化合物8-2可
以在大約0℃至大約40℃的溫度下,於像是N,N-二甲基甲醯胺之極性非質子性溶劑內,在一種胺鹼諸如三乙胺之存在下,與一種烷化試劑,諸如(C1-C4烷基)鹵化物、(C1-C4烷基)三氟甲磺酸,或是(C1-C4鹵烷基)三氟甲磺酸,進行反應以提供吡唑并[3,4-c]哌啶-2-酮硫化物化合物6-4(C,流程圖8B)。烷化試劑,諸如(C1-C4烷基)三氟甲磺酸或是(C1-C4鹵烷基)三氟甲磺酸,可以依據Tetrahedron Lett.2010,51,6542中概述的程序來製備。
在一些具體例中,該殺蟲組成物可包含式I-A的
吡唑并[3,4-c]哌啶-2-酮化合物或其任一農業上可接受的鹽類,其中當m為1或2時,R9為(C1-C4烷基)S(=O)m(C1-C4烷基)或(C1-C4烷基)S(=O)m(C1-C4鹵烷基),以及R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義。
在另一個具體例中,此吡唑并[3,4-c]哌啶-2-酮化
合物I-A,其中當m為1或2時,R9為(C1-C4烷基)S(=O)m(C1-C4烷基)或(C1-C4烷基)S(=O)m(C1-C4鹵烷基),可以如同流程圖9中所示予以製備。
如同流程圖9中所示,吡唑并[3,4-c]哌啶-2-酮硫
化物化合物6-4,其中R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以在範圍由大約40℃至大約70℃的溫度下,於像是乙酸之極性質子性溶劑內,藉由一種氧化劑諸如過氧硼酸鈉四水合物,予以氧化來提供對應的吡唑并[3,4-c]哌啶-2-酮亞碸化合物9-1及/或對應的吡唑并[3,4-c]哌啶-2-酮碸化合物9-2。
在一些具體例中,該殺蟲組成物可包含式I-A的
吡唑并[3,4-c]哌啶-2-酮化合物或其任一農業上可接受的鹽類,其中R9為C1-C4鹵烷基,以及R1、R2、R3、R4、R5、
R6、R7、R8及X1係如先前所定義。
在一個具體例中,此吡唑并[3,4-c]哌啶-2-酮化
合物I-A,其中R9為C1-C4鹵烷基,可以如同流程圖10中所示予以製備。
吡唑并[3,4-c]哌啶-2-酮酯化合物6-1,其中R1、
R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以在大概室溫下,於像是乙醇之極性質子性溶劑內,藉由一種諸如硼氫化鈉之還原劑,予以還原來提供對應的吡唑并[3,4-c]哌啶-2-酮醇化合物10-2(A,流程圖10)。
該吡唑并[3,4-c]哌啶-2-酮醇化合物10-2繼而可
以藉由一種氧化劑,諸如戴斯-馬丁氧化劑(Dess-Martin Periodinane),予以氧化來提供對應的吡唑并[3,4-c]哌啶-2-
酮醛化合物10-3(B,流程圖10)。
隨後,該吡唑并[3,4-c]哌啶-2-酮醛化合物10-3
可以在大約0℃至大約40℃的溫度下,於像是二氯甲烷之溶劑內,與一種氟化試劑,諸如二乙胺基三氟化硫(diethylaminosulfur trifluoride),進行反應以提供吡唑并[3,4-c]哌啶-2-酮化合物10-4(C,流程圖10)。
任擇地,該吡唑并[3,4-c]哌啶-2-酮醛化合物
10-3可以轉化成吡唑并[3,4-c]哌啶-2-酮化合物10-4,其係藉由在大約-78℃至大約室溫的溫度下,於像是四氫呋喃之溶劑內,用一種金屬化(metallated)烷基試劑,諸如烷基格任亞試劑(alkyl Grignard reagent),如溴化甲鎂來處理,接著如上所述予以氧化且氟化,而提供吡唑并[3,4-c]哌啶-2-酮化合物10-4(D,流程圖10)。
再者,任擇地,該吡唑并[3,4-c]哌啶-2-酮醛化
合物10-3可以用羅氏試劑(Ruppert’s reagent)(三氟甲基三甲基矽烷)來處理,接著如上所述予以氧化且氟化,而提供吡唑并[3,4-c]哌啶-2-酮化合物10-4(E,流程圖10)。
在一個具體例中,吡唑并[3,4-c]哌啶-2-酮化合
物I-A,其中R9為(C1-C4烷基)C(=O)(苯基),以及R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以如同流程圖11A中所示予以製備。
吡唑并[3,4-c]哌啶-2-酮酯化合物6-1,其中R1、
R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以轉化成對應的吡唑并[3,4-c]哌啶-2-酮N-甲氧基-N-甲醯胺(在下稱為“吡唑并[3,4-c]哌啶-2-酮Weinreb醯胺(pyrazolo[3,4-c]piperidin-2-one Weinreb amide)”)化合物11-1,其係藉由在大約室溫下,於諸如四氫呋喃和水之溶劑混合物內,用一種鹼諸如氫氧化鋰來處理(A,流程圖11A)。
繼而,吡唑并[3,4-c]哌啶-2-酮Weinreb醯胺化合
物11-1可以在大約-78℃至大約室溫的溫度下,於像是四氫呋喃之溶劑內,與一種金屬化(metallated)芳基物種,諸如芳基格任亞試劑(aryl Grignard reagent),如溴化苯鎂,進
行反應以提供吡唑并[3,4-c]哌啶-2-酮化合物11-2(B,流程圖11A)。Ar基團為一種具有或不具有任何取代基之芳香族基團,且可以或可以不包括一個或更多個雜原子。
在一個具體例中,吡唑并[3,4-c]哌啶-2-酮化合
物I-A,其中R9為(C1-C4烷基)(鹵烷基)(苯基),以及R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以如同流程圖11B中所示予以製備。
藉由用一種鹵化劑來處理吡唑并[3,4-c]哌啶-2-
酮化合物11-2,可以將吡唑并[3,4-c]哌啶-2-酮化合物11-2轉化成吡唑并[3,4-c]哌啶-2-酮化合物11-3。
作為非限制性實例,吡唑并[3,4-c]哌啶-2-酮化
合物11-2可以在大約0℃至大約40℃的溫度下,於像是二氯甲烷之溶劑內,用一種氟化試劑,諸如二乙胺基三氟化硫(diethylaminosulfur trifluoride),來處理以提供吡唑并[3,4-c]哌啶-2-酮化合物11-3。
作為非限制性實例,吡唑并[3,4-c]哌啶-2-酮化
合物11-2可以在大約0℃至大約40℃的溫度下,於像是二氯甲烷之溶劑內,用一種氟化試劑,諸如二乙胺基三氟化
硫,來處理以提供吡唑并[3,4-c]哌啶-2-酮化合物11-3。
在一個具體例中,吡唑并[3,4-c]哌啶-2-酮化合
物I-A,其中R9為(C1-C4烷基)(鹵烷基)(烷基),以及R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以如同流程圖11C中所示予以製備。
吡唑并[3,4-c]哌啶-2-酮Weinreb醯胺化合物
11-1,其中R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以在大約-78℃至大約室溫的溫度下,於像是四氫呋喃之溶劑內,用一種金屬化(metallated)烷基試劑,諸如烷基格任亞試劑(alkyl Grignard reagent),如溴化甲鎂來處理,而提供吡唑并[3,4-c]哌啶-2-酮酮化合物11-4(A,流程圖11C)。
繼而,吡唑并[3,4-c]哌啶-2-酮酮化合物11-4可
以藉由用一種鹵化劑來處理,而轉化成吡唑并[3,4-c]哌啶-2-酮化合物11-5,如同以上流程圖11B中所述。作為非限制性實例,吡唑并[3,4-c]哌啶-2-酮化合物11-4可以在大約0℃至大約40℃的溫度下,於像是二氯甲烷之溶劑之內,用一種氟化試劑,諸如二乙胺基三氟化硫,來處理以提供吡唑并[3,4-c]哌啶-2-酮化合物11-5(B,流程圖11C)。
在一些具體例中,該殺蟲組成物可包含式I-A的
吡唑并[3,4-c]哌啶-2-酮化合物或其任一農業上可接受的鹽類,其中R9為(C1-C4烷基)C(=NOR10)R11,R11為H,以及R1、R2、R3、R4、R5、R6、R7、R8、R10及X1係如先前所定義。
在另一個具體例中,此吡唑并[3,4-c]哌啶-2-酮
化合物I-A,其中R9為(C1-C4烷基)CH(=NOR10),可以如同流程圖12A中所示予以製備。
如同流程圖12A中所示,吡唑并[3,4-c]哌啶-2-
酮醛化合物10-3,其中R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以於像是乙醇之極性質子性溶劑內,具有或沒有一種酸,諸如乙酸,與一種羥胺化合物H2NOR10,其中R10係如先前所定義,進行反應以提供對應的吡唑并[3,4-c]哌啶-2-酮肟化合物12-1。
在一些具體例中,該殺蟲組成物可包含式I-A的
吡唑并[3,4-c]哌啶-2-酮化合物或其任一農業上可接受的鹽類,其中R9為(C1-C4烷基)C(=NOR10)R11,R11為C1-C4烷基,以及R1、R2、R3、R4、R5、R6、R7、R8、R10及X1係如先前所定義。
在一個具體例中,此吡唑并[3,4-c]哌啶-2-酮化
合物I-A,其中R9為(C1-C4烷基)C(=NOR10)(C1-C4烷基),可以如同流程圖12B中所示予以製備。
該吡唑并[3,4-c]哌啶-2-酮醛化合物10-3可以在
大約-78℃至大約室溫的溫度下,於像是四氫呋喃之溶劑內,與一種金屬化烷基試劑,諸如烷基格任亞試劑(alkyl Grignard reagent),如溴化甲鎂進行反應。繼而,生成的吡唑并[3,4-c]哌啶-2-酮化合物可以用一種氧化劑,諸如戴斯
-馬丁氧化劑(Dess-Martin Periodinane),來處理以提供吡唑并[3,4-c]哌啶-2-酮酮化合物10-4(A,流程圖12B)。
吡唑并[3,4-c]哌啶-2-酮酮化合物10-4繼而可以
於像是乙醇之極性質子性溶劑內,具有或沒有一種酸,諸如乙酸,與一種羥胺化合物H2NOR10,其中R10係如先前所定義,進行反應以提供對應的吡唑并[3,4-c]哌啶-2-酮酮-肟化合物(pyrazolo[3,4-c]piperidin-2-one keto-oxime)12-2(B,流程圖12B)。
在一些具體例中,該殺蟲組成物可包含式I-A的
吡唑并[3,4-c]哌啶-2-酮化合物或其任一農業上可接受的鹽類,其中R9為(C1-C4烷基)C(=NOR10)R11,R11為C1-C4鹵烷基,以及R1、R2、R3、R4、R5、R6、R7、R8、R10及X1係如先前所定義。
在另一個具體例中,此吡唑并[3,4-c]哌啶-2-酮
化合物I-A,其中R9為R9為(C1-C4烷基)C(=NOR10)(C1-C4鹵烷基),可以如同流程圖12C中所示予以製備。
該吡唑并[3,4-c]哌啶-2-酮醛化合物10-3可以與
一種三氟甲基化製劑,諸如羅氏試劑(Ruppert’s reagent)(亦即,三氟甲基三甲基矽烷)予以反應,接著如上所述予以氧化,而提供吡唑并[3,4-c]哌啶-2-酮酮化合物10-5(A,流程圖12C)。
隨後,吡唑并[3,4-c]哌啶-2-酮酮化合物10-5可
以於像是乙醇之極性質子性溶劑內,具有或沒有一種酸,諸如乙酸,與一種羥胺(hyroxylamine)化合物H2NOR10,其中R10係如先前所定義,進行反應以提供對應的吡唑并[3,4-c]哌啶-2-酮酮-肟化合物12-3(B,流程圖12C)。
在一些具體例中,該殺蟲組成物可包含式I-A的
吡唑并[3,4-c]哌啶-2-酮化合物或其任一農業上可接受的鹽類,其中R9為(C1-C4烷基)C(=NOR10)R11,R11為苯基或經取代的苯基,以及R1、R2、R3、R4、R5、R6、R7、R8、R10及X1係如先前所定義。
在一個具體例中,此吡唑并[3,4-c]哌啶-2-酮化
合物I-A,其中R9為(C1-C4烷基)C(=NOR10)R11,以及R11為苯基或經取代的苯基,可以如同流程圖12D中所示予以製備。
吡唑并[3,4-c]哌啶-2-酮Weinreb醯胺化合物
11-1,其中R1、R2、R3、R4、R5、R6、R7、R8及X1係如先前所定義,可以在大約-78℃至大約室溫的溫度下,於像是四氫呋喃之溶劑內,與一種金屬化芳基試劑,諸如芳基
格任亞試劑(aryl Grignard reagent),如溴化苯鎂,進行反應以提供吡唑并[3,4-c]哌啶-2-酮酮化合物10-6,其中R11為苯基或經取代的苯基(A,流程圖12D)。
隨後,吡唑并[3,4-c]哌啶-2-酮酮化合物10-6可
以於像是乙醇之極性質子性溶劑內,具有或沒有一種酸,諸如乙酸,與一種羥胺(hyroxylamine)化合物H2NOR10,其中R10係如先前所定義,進行反應以提供對應的吡唑并[3,4-c]哌啶-2-酮酮-肟化合物12-4,其中R11為苯基或經取代的苯基(B,流程圖12D)。
在一些具體例中,該殺蟲組成物可包含式I的化
合物或其任一農業上可接受的鹽類,其中n為0且Q為硫,如同以下的式I-B之吡唑并[3,4-c]哌啶-2-硫酮(thione)化合物:
在一特定的具體例中,吡唑并[3,4-c]哌啶-2-硫
酮化合物I-B可以如同流程圖13中所示予以製備。
式I-A的吡唑并[3,4-c]哌啶-2-酮化合物,其中R1、R2、R3、R4、R5、R6、R7、R8、R9及X1係如先前所定義,可以在溫度範圍由大約80℃至大約140℃之下,於標準加熱條件或微波條件下,於像是1,2-二氯乙烷或甲苯之非質子性溶劑內,與一種硫化試劑(thionation reagent),諸如路易斯試劑(Lawesson’s reagent),進行反應以提供式I-B之吡唑并[3,4-c]哌啶-2-硫酮化合物。殺蟲上可接受的酸加成鹽類、鹽衍生物、溶劑化物、酯衍生物、多形體、同位素、放射性核種及立體異構物
在一些具體例中,該式I的化合物可以調配成殺蟲上可接受的酸加成鹽類。作為非限制性例子,胺官能基可與氫氯酸、氫溴酸、硫酸、磷酸、乙酸、苯甲酸、檸檬酸、丙二酸、水楊酸、蘋果酸、福馬酸、草酸、琥珀酸、酒石酸、乳酸、葡萄糖酸、抗壞血酸、馬來酸、天冬門酸、苯磺酸、甲磺酸、乙磺酸、羥甲磺酸、羥乙磺酸,及三氟乙酸形成鹽類。另外,作為非限制性例子,酸官能基可形成包括自鹼金屬或鹼土金屬衍生及自氨及胺衍生之鹽類。陽離子之非限制性例子可包括鈉、鉀,或是鎂。
於其他的具體例中,該式I的化合物可以調配成
鹽衍生物。作為非限制性例子,鹽衍生物可藉由可藉由使游離鹼與足夠量之所欲酸接觸產生鹽而製備。游離鹼可藉由將此鹽以適合的稀釋鹼水溶液處理而再生,鹼水溶液諸如但不限於稀釋的氫氧化鈉(NaOH)、碳酸鉀、氨,及碳酸氫鈉水溶液。
於另外的具體例中,該式I的化合物可以與溶劑調配成穩定的錯合物,從而使該錯合物在移除未錯合的溶劑後仍保持完整。此等錯合物經常被稱為「溶劑合物」。與作為溶劑之水形成穩定的水合物為所希望的。
在一些具體例中,該式I的化合物可以製成酯衍生物。
在特定的具體例中,該式I的化合物可以製成各種結晶性多形體。多形體於發展農用化學品係重要的,因為相同分子之不同結晶多形體或結構的具有的不同的物理性質及生物效能。
於另外的具體例中,該式I的化合物可以用不同的同位素來製造。尤其重要的為具有代替1H之2H(亦稱為氘)之分子。
在一些具體例中,該式I的化合物可以用不同的放射性核種來製造。尤其重要的為具有13C或14C之分子。
於其他的具體例中,該式I的化合物可以以一種或多種立體異構物形式存在。因此,某些分子可以外消旋混合物形式生產。熟習此項技術者將瞭解,一種立體異構
物可比其他立體異構物更具活性。個別立體異構物可藉由已知的選擇性合成程序獲得、使用經解析之起始物質藉由習知合成程序獲得,或是藉由習知解析程序來獲得。此專利申請案中揭示之某些化合物可以兩種或兩種以上異構物形式存在。各種異構物包括幾何異構物、非對映異構物或是對映異構物。因此,此專利申請案中揭示之化合物可以包括幾何異構物、外消旋混合物、個別立體異構物或是光學活性混合物。熟習此項技術者將瞭解,一種異構物可比其他異構物更具活性。本揭示中揭露之結構,為了清楚之故可僅以一種幾何形式繪製,但是意欲表示該化合物之所有幾何形式。
在一特定的具體例中,一種殺蟲組成物包含該式I的化合物,或其任一農業上可接受的鹽類。
在一些具體例中,一種殺蟲組成物包含該式I的化合物或其任一農業上可接受的鹽類,以及植物學上可接受之惰性載劑(諸如,固態載劑或液態載劑)。
在另一個具體例中,該殺蟲組成物可以進一步包含至少一種選自於下列之添加劑:界面活性劑、安定劑、催吐劑、崩散劑、消泡劑、潤濕劑、分散劑、結合劑、染料或填料。
在特定的具體例中,該殺蟲組成物可以處於固態形式。固態形式之非限制性例子可包括粉末、粉塵,或是顆粒調配物。
於其他的具體例中,該殺蟲組成物可以處於液態調配物形式。液態形式之例子可包括但不限於,配於合適的載劑中之分散液、懸浮液、乳劑或溶液。
於另外的具體例中,該殺蟲組成物可以處於液態分散液形式,其中該式I的化合物可以分散於水中或其他農業上適合的液態載劑中。
於再另外的具體例中,該殺蟲組成物可以處於溶液形式配於合適的有機溶劑中。在一個具體例中,廣泛地在農業化學中使用之噴霧油,可使用作為供該殺蟲組成物用之有機溶劑。
該殺蟲組成物可結合一種或多種具有殺蜱蟎、殺藻、殺鳥(avicidal)、殺菌、殺真菌、除草、殺昆蟲、殺軟體動物、殺線蟲、滅鼠及/或殺病毒特性之化合物一起使用(諸如,呈組成混合物之形式,或同時或依序施用)。
再者,該殺蟲組成物可結合一種或多種拒食劑、驅鳥劑、化學絕育劑、除草劑安全劑、誘蟲劑、驅蟲劑、驅哺乳動物劑、交配干擾劑、植物活化劑、植物生長調節劑及/或協力劑之化合物一起使用(諸如,呈組成混合物之形式,或同時或依序施用)。
可以與該式I的化合物組合使用之殺昆蟲劑的非限制性例子可包括:1,2-二氯丙烷、阿巴汀(abamectin)、毆殺松(acephate)、亞滅培(acetamiprid)、家蠅磷(acethion)、乙醯蟲腈(acetoprole)、阿納寧(acrinathrin)、丙
烯腈、棉鈴威(alanycarb)、得滅克(aldicarb)、涕滅碸威(aldoxycarb)、阿特靈(aldrin)、亞列寧(allethrin)、阿洛胺菌素(allosamidin)、除害威(allyxycarb)、α-賽滅寧(alpha-cypermethrin)、α-蛻皮激素(α-ecdysone)、α/p/ω-安殺番(α/p/ω-endosulfan)、賽硫磷(amidithion)、滅害威(aminocarb)、阿米通(amiton)、草酸阿米通、三亞蟎(amitraz)、安納巴松(anabasine)、乙基殺撲磷(athidathion)、印苦楝子素(azadirachtin)、亞滅松(azamethiphos)、乙基谷速松(azinphos-ethyl)、谷速松(azinphos-methyl)、偶氮磷(azothoate)、六氟矽酸鋇、椒菊酯(barthrin)、免敵克(bendiocarb)、免扶克(benfuracarb)、免速達(bensultap)、β-賽扶寧(cyfluthrin)、ζ-賽滅寧(zeta-cypermethrin)、畢芬寧(bifenthrin)、百亞列寧(bioallethrin)、苄呋烯菊酯(bioethanomethrin)、生物氯菊酯(biopermethrin)、雙三氟蟲脲(bistrifluron)、硼砂、硼酸、溴苯烯磷(bromfenvinfos)、保滿丹(bromocyclen)、溴-滴滴涕(DDT)、溴磷松(bromophos)、乙基溴磷松、必克蝨(bufencarb)、布芬淨(buprofezin)、畜蟲威(butacarb)、佈伏斯(butathiofos)、佈嘉信(butocarboxim)、布托酯(butonate)、丁酮碸威(butoxycarboxim)、硫線磷(cadusafos)、砷酸鈣、多硫化鈣、毒殺芬(camphechlor)、氯滅殺威(carbanolate)、胺甲(carbaryl)、加保扶(carbofuran)、二硫化碳、四氯化碳、加芬松(carbophenothion)、丁基加保扶(carbosulfan)、培丹
(cartap)、培丹鹽酸鹽、剋安勃(chlorantraniliprole)、冰片丹(chlorbicyclen)、可氯丹(chlordane)、氯癸酮(chlordecone)、氯苯甲脒(chlordimeform)、氯苯甲脒鹽酸鹽、氯氧磷(chlorethoxyfos)、克凡派(chlorfenapyr)、氯芬松(chlorfenvinphos)、克福隆(chlorfluazuron)、氯甲磷(chlormephos)、氯仿、氯化苦(chloropicrin)、氯辛硫磷(chlorphoxim)、滅蟲吡啶(chlorprazophos)、陶斯松(chlorpyrifos)、甲基陶斯松(chlorpyrifos)、克硫松(chlorthiophos)、可芬諾(chromafenozide)、瓜菊酯(cinerin)I、瓜菊酯II、瓜菊酯類(cinerins)、順式苄呋菊酯(cismethrin)、除線威(cloethocarb)、氯氰碘柳胺(closantel)、可尼丁(clothianidin)、乙醯亞砷酸銅、砷酸銅、萘酸銅、油酸銅、蠅毒磷(coumaphos)、畜蟲磷(coumithoate)、克羅米通(crotamiton)、丁烯磷(crotoxyphos)、育畜磷(crufomate)、冰晶石(cryolite)、施力松(cyanofenphos)、氰乃松(cyanophos)、果蟲磷(cyanthoate)、氰蟲醯胺(cyantraniliprole)、環戊烯菊酯(cyclethrin)、乙氰菊酯(cycloprothrin)、賽扶寧(cyfluthrin)、賽洛寧(cyhalothrin)、賽滅寧(cypermethrin)、賽芬寧(cyphenothrin)、賽滅淨(cyromazine)、賽滅磷(cythioate)、滴滴涕(DDT)、去甲基克百威(decarbofuran)、第滅寧(deltamethrin)、甲基滅賜松(demephion)、甲基滅賜松-O、甲基滅賜松-S、內吸磷(demeton)、甲基內吸磷、內吸磷-O、甲基內吸磷-O、內吸磷-S、甲基內吸磷-S、碸吸
磷(demeton-S-methylsulphon)、汰芬隆(diafenthiuron)、得拉松(dialifos)、矽藻土、大利松(diazinon)、異氯磷(dicapthon)、除線磷(dichlofenthion)、二氯松(dichlorvos)、大跨希(dicresyl)、雙特松(dicrotophos)、環蟲腈(dicyclanil)、地特靈(dieldrin)、二福隆(diflubenzuron)、二羥丙茶鹼(dilor)、四氟甲醚菊酯(dimefluthrin)、甲氟磷(dimefox)、地麥威(dimetan)、大滅松(dimethoate)、苄菊酯(dimethrin)、二甲基亞硝胺(dimethylvinphos)、敵蠅威(dimetilan)、消蟎酚(dinex)、消蟎酚-帝克列杉(dinex-diclexine)、硝丙酚(dinoprop)、戊硝酚(dinosam)、達特南(dinotefuran)、苯蟲醚(diofenolan)、殺力松(dioxabenzofos)、二氧威(dioxacarb)、大克松(dioxathion)、二硫松(disulfoton)、大賽伏(dithicrofos)、春芹烯(d-limonene)、DNOC、DNOC-銨、DNOC-鉀、DNOC-鈉、多滅蟲(doramectin)、蛻皮甾酮(ecdysterone)、因滅汀(emamectin)、因滅汀苯甲酸鹽、EMPC、益避寧(empenthrin)、安殺番(endosulfan)、因毒磷(endothion)、安特靈(endrin)、EPN、保幼醚(epofenonane)、乙醯胺基阿維菌素(eprinomectin)、富右旋反式丙烯菊酯(esdépalléthrine)、益化利(esfenvalerate)、抑他風(etaphos)、愛芬克(ethiofencarb)、愛殺松(ethion)、乙蟲腈(ethiprole)、益硫磷(ethoate-methyl)、普伏松(ethoprophos)、甲酸乙酯、乙基-DDD、二溴化乙烯、二氯化乙烯、環氧乙烷、依芬寧(etofenprox)、益多松
(etrimfos)、EXD、胺磺磷(famphur)、芬滅松(fenamiphos)、抗蟎唑(fenazaflor)、樂乃松(fenchlorphos)、芬硫克(fenethacarb)、五氟苯菊酯(fenfluthrin)、撲滅松(fenitrothion)、丁基滅必蝨(fenobucarb)、芬噁寧(fenoxacrim)、芬諾克(fenoxycarb)、吡氯氰菊酯(fenpirithrin)、芬普寧(fenpropathrin)、繁福松(fensulfothion)、芬殺松(fenthion)、乙基芬殺松、芬化利(fenvalerate)、芬普尼(fipronil)、氟尼胺(flonicamid)、氟蟲醯胺(flubendiamide)(其附加的分解型異構物)、伏克隆(flucofuron)、氟蟎脲(flucycloxuron)、護賽寧(flucythrinate)、嘧蟲胺(flufenerim)、氟芬隆(flufenoxuron)、三氟醚菊酯(flufenprox)、福化利(fluvalinate)、大福松(fonofos)、覆滅蟎(formetanate)、覆滅蟎鹽酸鹽、福木松(formothion)、藻蟎威(formparanate)、藻蟎威鹽酸鹽、丁苯硫磷(fosmethilan)、甲基氯吡磷(fospirate)、丁硫環磷(fosthietan)、呋喃蟲醯肼(fufenozide)、呋線威(furathiocarb)、糠醛菊酯(furethrin)、γ-賽洛寧(cyhalothrin)、γ-HCH、合芬寧(halfenprox)、合芬隆(halofenozide)、HCH、HEOD、飛佈達(heptachlor)、飛達松(heptenophos)、速殺硫磷(heterophos)、六伏隆(hexaflumuron)、HHDN、愛美隆(hydramethylnon)、氰化氫、烯蟲乙酯(hydroprene)、水奎威(hyquincarb)、益達胺(imidacloprid)、依普寧(imiprothrin)、因得克(indoxacarb)、碘甲烷、IPSP、依殺松(isazofos)、碳氯靈
(isobenzan)、水胺硫磷(isocarbophos)、異氯甲橋(isodrin)、亞芬松(isofenphos)、甲基亞芬松、滅必蝨(isoprocarb)、亞賜圃(isoprothiolane)、獲賜松(isothioate)、加褔松(isoxathion)、依維菌素(ivermectin)、茉酮菊酯(jasmolin)I、茉酮菊酯II、護粒松(jodfenphos)、青春激素I(juvenile hormoneI)、青春激素II、青春激素III、氯戊環(kelevan)、烯蟲炔酯(kinoprene)、λ-賽洛寧(cyhalothrin)、砷酸鉛、里琵菌素(lepimectin)、福賜松(leptophos)、靈丹(lindane)、力輪松(lirimfos)、祿芬隆(lufenuron)、噻唑磷(lythidathion)、馬拉松(malathion)、特蟎腈(malonoben)、疊氮磷(mazidox)、滅加松(mecarbam)、四甲磷(mecarphon)、美納松(menazon)、氯氟醚菊酯(meperfluthrin)、美福松(mephosfolan)、氯化亞汞、倍硫磷亞碸(mesulfenfos)、美氟綜(metaflumizone)、滅克松(methacrifos)、達馬松(methamidophos)、滅大松(methidathion)、滅賜克(methiocarb)、殺蟲乙烯磷(methocrotophos)、納乃得(methomyl)、美賜平(methoprene)、甲醚菊酯(methothrin)、甲氧滴滴涕(methoxychlor)、滅芬諾(methoxyfenozide)、溴甲烷、異硫氰酸甲酯、甲氯仿、二氯甲烷、美特寧(metofluthrin)、治滅蝨(metolcarb)、蟲酮(metoxadiazone)、美文松(mevinphos)、治克威(mexacarbate)、密滅汀(milbemectin)、倍脈心(milbemycin oxime)、丙胺氟磷(mipafox)、滅蟻樂(mirex)、殺蟲單(molosultap)、亞素靈
(monocrotophos)、殺蟲單(monomehypo)、殺蟲單(monosultap)、茂硫磷(morphothion)、莫西菌素(moxidectin)、萘肽磷(naftalofos)、乃力松(naled)、萘、尼古丁、伏蟻靈(nifluridide)、烯啶蟲胺(nitenpyram)、硝乙脲噻唑(nithiazine)、戊氰威(nitrilacarb)、諾伐隆(novaluron)、多氟脲(noviflumuron)、歐滅松(omethoate)、歐殺滅(oxamyl)、滅多松(oxydemeton-methyl)、異亞碸磷(oxydeprofos)、碸拌磷(oxydisulfoton)、對-二氯苯、巴拉松(parathion)、甲基巴拉松、氟幼脲(penfluron)、五氯酚、百滅寧(permethrin)、芬硫磷(phenkapton)、酚丁滅寧(phenothrin)、賽達松(phenthoate)、福瑞松(phorate)、裕必松(phosalone)、硫環磷(phosfolan)、益滅松(phosmet)、對氯硫磷(phosnichlor)、福賜米松(phosphamidon)、膦、巴賽松(phoxim)、甲基巴賽松、必美松(pirimetaphos)、比加普(pirimicarb)、必滅松(pirimiphos-ethyl)、亞特松(pirimiphos-methyl)、亞砷酸鉀、硫氰化鉀、4,4-滴滴涕(pp’-DDT)、普亞烈寧(prallethrin)、早熟素I(precocene I)、早熟素II、早熟素III、嘧啶松(primidophos)、佈飛松(profenofos)、環丙氟靈(profluralin)、丙氟菊酯(profluthrin)、蜱虱威(promacyl)、普滅克(promecarb)、加護松(propaphos)、撲達松(propetamphos)、安丹(propoxur)、乙噻唑磷(prothidathion)、普硫松(prothiofos)、飛克松(prothoate)、丙苯烴菊酯(protrifenbute)、派滅淨(pymetrozine)、白克松
(pyraclofos)、必伏清(pyrafluprole)、白粉松(pyrazophos)、吡菊酯(pyresmethrin)、除蟲菊精I、除蟲菊精II、除蟲菊精類、畢達本(pyridaben)、啶蟲丙醚(pyridalyl)、必芬松(pyridaphenthion)、氟蟲吡喹(pyrifluquinazon)、畢汰芬(pyrimidifen)、嘧硫磷(pyrimitate)、必清(pyriprole)、百利普芬(pyriproxyfen)、苦木(quassia)、拜裕松(quinalphos)、甲基拜裕松、畜寧磷(quinothion)、碘醚柳胺(rafoxanide)、列滅寧(resmethrin)、魚藤酮(rotenone)、蘭尼汀(ryania)、藜蘆鹼(sabadilla)、八甲焦磷醯胺(schradan)、色拉菌素(selamectin)、矽護芬(silafluofen)、矽膠劑、亞砷酸鈉、氟化鈉、六氟矽酸鈉、硫氰酸鈉、蘇硫磷(sophamide)、賜諾特(spinetoram)、賜諾殺(spinosad)、螺甲蟎酯(spiromesifen)、螺蟲乙酯(spirotetramat)、殺克隆(sulcofuron)、殺克隆-鈉、氟蟲胺(sulfluramid)、治螟磷(sulfotep)、氟啶蟲胺腈(sulfoxaflor)、磺醯氟、硫丙磷(sulprofos)、τ-福化利(fluvalinate)、噻蟎威(tazimcarb)、TDE、得芬諾(tebufenozide)、得芬瑞(tebufenpyrad)、丁基嘧啶磷(tebupirimfos)、得福隆(teflubenzuron)、汰福寧(tefluthrin)、亞培松(temephos)、TEPP、環戊烯丙菊酯(terallethrin)、托福松(terbufos)、四氯乙烷、樂本松(tetrachlorvinphos)、治滅寧(tetramethrin)、四氟醚菊酯(tetramethylfluthrin)、θ-賽滅寧(cypermethrin)、賽果培(thiacloprid)、賽速安(thiamethoxam)、賽伏(thicrofos)、抗蟲威(thiocarboxime)、硫賜安(thiocyclam)、硫賜安草酸
鹽、硫敵克(thiodicarb)、硫伐隆(thiofanox)、硫滅松(thiometon)、殺蟲雙(thiosultap)、殺蟲雙二鈉、殺蟲雙單鈉、蘇力菌素(thuringiensin)、脫芬瑞(tolfenpyrad)、泰滅寧(tralomethrin)、拜富寧(transfluthrin)、反式百滅寧(transpermethrin)、三苯噻蟎吩(triarathene)、唑蚜威(triazamate)、三落松(triazophos)、三氯松(trichlorfon)、樂乃松(trichlormetaphos)-3、毒壤膦(trichloronat)、三氯丙氧磷(trifenofos)、三福隆(triflumuron)、混殺威(trimethacarb)、烯蟲硫酯(triprene)、繁米松(vamidothion)、凡力(vaniliprole)、XMC、滅爾蝨(xylylcarb)、ζ-賽滅寧(cypermethrin),或是左拉伏(zolaprofos)。
可以與該式I的化合物組合使用之殺蜱蟎劑的非限制性例子可包括:亞醌蟎(acequinocyl)、磺胺蟎酯(amidoflumet)、三氧化二砷、偶氮苯(azobenzene)、亞環錫(azocyclotin)、免賴得(benomyl)、苯磷(benoxafos)、西脫蟎(benzoximate)、苯甲酸苄酯、必芬蟎(bifenazate)、百蟎克(binapacryl)、新殺蟎(bromopropylate)、蟎離丹(chinomethionat)、氯殺蟎(chlorbenside)、殺蟎醇(chlorfenethol)、殺蟎酯(chlorfenson)、敵蟎丹(chlorfensulphide)、克氯苯(chlorobenzilate)、滅蟎脒(chloromebuform)、滅蟲脲(chloromethiuron)、克氯蟎(chloropropylate)、克芬蟎(clofentezine)、唑蟎氰
(cyenopyrafen)、賽芬蟎(cyflumetofen)、錫蟎丹(cyhexatin)、益發靈(dichlofluanid)、大克蟎(dicofol)、得氯蟎(dienochlor)、氟蟎(diflovidazin)、大脫蟎(dinobuton)、白粉克(dinocap)、白粉克-4、白粉克-6、敵蟎消(dinocton)、硝戊酯(dinopenton)、硝辛酯殺蟎劑(dinosulfon)、硝丁酯(dinoterbon)、二苯碸、二硫龍(disulfiram)、朵芬娜賓(dofenapyn)、依殺蟎(etoxazole)、芬殺蟎(fenazaquin)、芬佈賜(fenbutatin oxide)、芬硫克(fenothiocarb)、芬普蟎(fenpyroximate)、芬蟎酯(fenson)、芳氟胺(fentrifanil)、嘧蟎酯(fluacrypyrim)、氟啶蜱脲(fluazuron)、氟苯并胺噻唑(flubenzimine)、聯苯氟(fluenetil)、氟氯苯菊酯(flumethrin)、氟殺蟎(fluorbenside)、合賽多(hexythiazox)、甲硫酚(mesulfen)、MNAF、尼可黴素(nikkomycin)、丙氯醇(proclonol)、毆蟎多(propargite)、喹硫磷(quintiofos)、賜派芬(spirodiclofen)、舒非侖(sulfiram)、硫、得脫蟎(tetradifon)、殺蟎黴素(tetranactin)、殺蟎硫醚(tetrasul),或是克殺蟎(thioquinox)。
可以與該式I的化合物組合使用之殺線蟲劑的非限制性例子可包括:1,3-二氯丙烯、異噻蟲唑(benclothiaz)、邁隆(dazomet)、邁隆-鈉、DBCP、DCIP、除線特(diamidafos)、氟噻蟲碸(fluensulfone)、福賽絕(fosthiazate)、糠醛(furfural)、新煙鹼類(imicyafos)、依殺
米朵孚斯(isamidofos)、依殺松(isazofos)、斯美地(metam)、斯美地銨、斯美地鉀、斯美地鈉、磷克(phosphocarb),或是治線磷(thionazin)。
可以與該式I的化合物組合使用之殺真菌劑的非限制性例子可包括:(3-乙氧基丙基)溴化汞、2-甲氧基乙基氯化汞、2-苯基酚、8-羥基喹啉硫酸鹽、8-苯基汞氧基喹啉、阿拉酸式苯(acibenzolar)、阿拉酸式苯(acibenzolar)-S-甲基、阿西佩它克斯(acypetacs)、阿西佩它克斯-銅(acypetacs-copper)、阿西佩它克斯-鋅(acypetacs-zinc)、十二嗎啉(aldimorph)、烯丙醇、辛唑嘧菌胺(ametoctradin)、安美速(amisulbrom)、1-胺基丙基磷酸(ampropylfos)、敵菌靈(anilazine)、金色制黴素(aureofungin)、氧環唑(azaconazole)、塞侖(azithiram)、亞托敏(azoxystrobin)、多硫化鋇、本達樂(benalaxyl)、本達樂-M、麥鏽靈(benodanil)、免賴得(benomyl)、醌肟腙(benquinox)、苯他隆(bentaluron)、苯噻菌胺(benthiavalicarb)、苯噻菌胺-異丙基、氯化烷基二甲基苄基銨、苯瑪松(benzamacril)、苯瑪松-異丁基(benzamacril-isobutyl)、抑菌啉(benzamorf)、苯基異羥肟酸(benzohydroxamic acid)、比托沙(bethoxazin)、百蟎克(binapacryl)、聯苯、比多農(bitertanol)、硫雙二氯酚(bithionol)、聯苯吡菌胺(bixafen)、保米黴素(blasticidin-S)、波爾多(Bordeaux)混合液、白克列
(boscalid)、溴克座(bromuconazole)、布瑞莫(bupirimate)、勃根第(Burgundy)混合液、得滅多(buthiobate)、丁基胺、多硫化鈣、四氯丹(captafol)、蓋普丹(captan)、嗎菌威(carbamorph)、貝芬替(carbendazim)、萎鏽靈(carboxin)、加普胺(carpropamid)、香芹酮(carvone)、切欣特(Cheshunt)混合液、蟎離丹(chinomethionat)、克氯綜(chlobenthiazone)、雙胺靈(chloraniformethan)、克氯尼(chloranil)、2-(2-氯苯基)-1H-苯并咪唑(chlorfenazole)、氯二硝萘(chlorodinitronaphthalene)、二氯甲氧苯(chloroneb)、氯化苦(chloropicrin)、四氯異苯腈(chlorothalonil)、四氯喹啉(chlorquinox)、克氯得(chlozolinate)、甘寶素(climbazole)、克黴唑(clotrimazole)、乙酸銅、碳酸銅、鹼式、氫氧化銅、萘酸銅、油酸銅、氯氧化銅、矽酸銅、硫酸銅、鉻酸銅鋅、甲酚(cresol)、銅合浦單劑(cufraneb)、福美銅氯(cuprobam)、氧化亞銅、賽座滅(cyazofamid)、環菌胺(cyclafuramid)、環己醯亞胺(cycloheximide)、賽芬胺(cyflufenamid)、克絕(cymoxanil)、伏賜丁(cypendazole)、環克座(cyproconazole)、賽普洛(cyprodinil)、邁隆(dazomet)、邁隆-鈉、DBCP、咪菌威(debacarb)、癸磷錫(decafentin)、去氫乙酸、益發靈(dichlofluanid)、二氯萘醌(dichlone)、二氯酚(dichlorophen)、賜克滅(dichlozoline)、苄氯三唑醇(diclobutrazol)、雙氯氰菌胺(diclocymet)、達滅淨(diclomezine)、達滅淨-鈉、大克爛(dicloran)、乙黴威
(diethofencarb)、焦碳酸二乙酯(diethyl pyrocarbonate)、待克利(difenoconazole)、二氟林(diflumetorim)、二甲嘧酚(dimethirimol)、達滅芬(dimethomorph)、醚菌胺(dimoxystrobin)、達克利(diniconazole)、達克利-M、大脫蟎(dinobuton)、白粉克(dinocap)、白粉克-4、白粉克-6、敵蟎消(dinocton)、硝戊酯(dinopenton)、硝辛酯殺蟎劑(dinosulfon)、硝丁酯(dinoterbon)、二苯胺、雙硫氧吡啶(dipyrithione)、二硫龍(disulfiram)、普得松(ditalimfos)、腈硫醌(dithianon)、DNOC、DNOC-銨、DNOC-鉀、DNOC-鈉、十二環啉(dodemorph)、十二環啉(dodemorph)乙酸鹽、十二環啉苯甲酸鹽、多地辛(dodicin)、多地辛-鈉、多寧(dodine)、肼菌酮(drazoxolon)、護粒松(edifenphos)、依普座(epoxiconazole)、乙環唑(etaconazole)、益地安(etem)、噻唑菌胺(ethaboxam)、依瑞莫(ethirimol)、乙氧基喹啉(ethoxyquin)、乙基汞2,3-二羥基丙基硫醇酯、乙基乙酸汞、乙基溴化汞、乙基氯化汞、乙基磷酸汞、依得利(etridiazole)、凡殺同(famoxadone)、咪唑菌酮(fenamidone)、敵磺鈉(fenaminosulf)、咪菌腈(fenapanil)、芬瑞莫(fenarimol)、芬克座(fenbuconazole)、甲呋醯胺(fenfuram)、環醯菌胺(fenhexamid)、種衣酯(fenitropan)、芬諾尼(fenoxanil)、拌種咯(fenpiclonil)、苯鏽啶(fenpropidin)、芬普福(fenpropimorph)、三苯錫(fentin)、三苯錫氯、三苯羥錫、富爾邦(ferbam)、富米綜
(ferimzone)、扶吉胺(fluazinam)、護汰寧(fludioxonil)、氟醯菌胺(flumetover)、氟啉(flumorph)、氟比來(fluopicolide)、氟吡菌醯胺(fluopyram)、氟醯亞胺、三氟苯唑(fluotrimazole)、氟嘧菌酯(fluoxastrobin)、氟喹唑(fluquinconazole)、護矽得(flusilazole)、氟硫滅(flusulfamide)、氟停安(flutianil)、福多寧(flutolanil)、護汰芬(flutriafol)、氟唑菌醯胺(fluxapyroxad)、福爾培(folpet)、甲醛、福賽得(fosetyl)、福賽得鋁(fosetyl-aluminium)、麥穗寧(fuberidazole)、呋霜靈(furalaxyl)、福拉比(furametpyr)、二甲呋醯胺(furcarbanil)、呋菌唑(furconazole)、呋菌唑(furconazole)-順式、糠醛、拌種胺(furmecyclox)、呋甲硫菌靈(furophanate)、固毆寧(glyodin)、灰黃黴素(griseofulvin)、雙胍辛(guazatine)、丙烯酸喹啉酯(halacrinate)、六氯苯、六氯丁二烯、菲克利(hexaconazole)、己硫松(hexylthiofos)、汞加芬(hydrargaphen)、殺紋寧(hymexazol)、依滅列(imazalil)、依滅列(imazalil)硝酸鹽、依滅列(imazalil)硫酸鹽、易胺座(imibenconazole)、克熱淨(iminoctadine)、克熱淨三乙酸鹽、克熱淨三苯磺酸鹽(iminoctadine trialbesilate)、碘甲烷(iodomethane)、種菌唑(ipconazole)、丙基喜樂松(iprobenfos)、依普同(iprodione)、異丙菌威(iprovalicarb)、亞賜圃(isoprothiolane)、萘吡菌胺(isopyrazam)、異噻菌胺(isotianil)、異凡二酮(isovaledione)、嘉賜黴素
(kasugamycin)、克收欣(kresoxim-methyl)、代森錳銅(mancopper)、鋅錳乃浦(mancozeb)、曼普胺(mandipropamid)、錳乃浦(maneb)、巴斯丹(mebenil)、苯并威(mecarbinzid)、滅派林(mepanipyrim)、滅普寧(mepronil)、敵蟎普(meptyldinocap)、氯化汞、氧化汞、氯化亞汞、滅達樂(metalaxyl)、右滅達樂(metalaxyl-M)、斯美地(metam)、斯美地銨、斯美地鉀、斯美地鈉、間氯敵菌酮(metazoxolon)、滅特座(metconazole)、滅速克(methasulfocarb)、呋菌胺(methfuroxam)、溴甲烷、異硫氰酸甲酯、甲基苯甲酸汞、甲基汞二氰二胺、甲基五氯苯氧化汞、免得爛(metiram)、苯氧菌胺(metominostrobin)、滅芬農(metrafenone)、噻菌胺(metsulfovax)、代森環(milneb)、邁克尼(myclobutanil)、滅克寧(myclozolin)、N-(乙基汞)-對-甲苯磺醯胺苯、代森鈉(nabam)、納他黴素(natamycin)、硝苯乙烯(nitrostyrene)、酞菌酯(nitrothal-isopropyl)、尼瑞莫(nuarimol)、OCH、辛噻酮(octhilinone)、呋醯胺(ofurace)、肟醚菌胺(orysastrobin)、毆殺斯(oxadixyl)、快得寧(oxine-copper)、咪唑(oxpoconazole)、咪唑反丁烯二酸鹽、嘉保信(oxycarboxin)、披扶座(pefurazoate)、平克座(penconazole)、賓克隆(pencycuron)、戊苯吡菌胺(penflufen)、五氯酚、吡噻菌胺(penthiopyrad)、苯基汞脲(phenylmercuriurea)、苯基汞乙酸鹽(phenylmercury acetate)、苯基汞氯化物(phenylmercury chloride)、焦兒茶
酚之苯基汞衍生物(phenylmercury derivative of pyrocatechol)、硝酸苯汞(phenylmercury nitrate)、苯基汞水楊酸鹽(phenylmercury salicylate)、氯瘟磷(phosdiphen)、熱必斯(phthalide)、啶氧菌酯(picoxystrobin)、哌丙靈(piperalin)、聚胺甲酸酯、保粒黴素(polyoxins)、保粒黴素丁(polyoxorim)、保粒黴素丁-鋅、疊氮化鉀(potassium azide)、多硫化鉀(potassium polysulfide)、硫氰酸鉀(potassium thiocyanate)、撲殺熱(probenazole)、撲克拉(prochloraz)、撲滅寧(procymidone)、普拔克(propamocarb)、普拔克鹽酸鹽(propamocarb hydrochloride)、普克利(propiconazole)、甲基鋅乃浦(propineb)、丙氧喹啉(proquinazid)、胺丙威(prothiocarb)、胺丙威(prothiocarb)鹽酸鹽、丙硫菌唑(prothioconazole)、賜加落(pyracarbolid)、百克敏(pyraclostrobin)、百克敏(pyraclostrobin)、唑胺菌酯(pyrametostrobin)、唑菌酯(pyraoxystrobin)、白粉松(pyrazophos)、吡菌苯威(pyribencarb)、雙滴保(pyridinitril)、比芬諾(pyrifenox)、派美尼(pyrimethanil)、甲氧苯啶菌(pyriofenone)、百快隆(pyroquilon)、氯甲氧吡啶(pyroxychlor)、氯吡根呋醚(pyroxyfur)、喹烯酮(quinacetol)、喹烯酮硫酸鹽、醌菌腙(quinazamid)、喹克座(quinconazole)、快諾芬(quinoxyfen)、五氯硝苯(quintozene)、吡咪唑(rabenzazole)、柳醯胺苯、環丙吡菌胺(sedaxane)、矽噻菌胺(silthiofam)、矽氟唑
(simeconazole)、疊氮化鈉(sodium azide)、鄰苯基苯酚化鈉(sodium orthophenylphenoxide)、五氯酚鈉(sodium pentachlorophenoxide)、多硫化鈉(sodium polysulfide)、螺環菌胺(spiroxamine)、鏈黴素(streptomycin)、硫、戊苯碸(sultropen)、TCMTB、得克利(tebuconazole)、異丁乙氧喹啉(tebufloquin)、克枯爛(tecloftalam)、四氯硝基苯(tecnazene)、福美雙聯(tecoram)、四克利(tetraconazole)、腐絕(thiabendazole)、噻噠氟(thiadifluor)、噻菌腈(thicyofen)、賽氟滅(thifluzamide)、硫氯苯亞胺(thiochlorfenphim)、硫柳汞(thiomersal)、多保淨(thiophanate)、甲基多保淨(thiophanate)、克殺蟎(thioquinox)、得恩地(thiram)、噻醯菌胺(tiadinil)、替係米(tioxymid)、脫克松(tolclofos-methyl)、甲基益發靈(tolylfluanid)、甲苯基乙酸汞、三泰芬(triadimefon)、三泰隆(triadimenol)、三唑磷胺(triamiphos)、嘧菌醇(triarimol)、丁三唑(triazbutil)、唑菌(triazoxide)、氧化三丁基錫、水楊菌胺(trichlamide)、三賽唑(tricyclazole)、三得芬(tridemorph)、三氟敏(trifloxystrobin)、賽福座(triflumizole)、賽福寧(triforine)、滅菌唑(triticonazole)、單克素(uniconazole)、單克素(uniconazole)-P、維利黴素(validamycin)、伐利芬奈蕾特(valifenalate)、免克寧(vinclozolin)、氰菌胺(zarilamid)、萘酸鋅、鋅乃浦(zineb)、福美鋅(ziram),或是座賽胺(zoxamide)。
可以與該式I的化合物組合使用之除草劑的非限
制性例子可包括:替拔草(2,3,6-TBA)、替拔草(2,3,6-TBA)-二甲基銨、替拔草(2,3,6-TBA)-鈉、2,4,5-T、2,4,5-T-2-丁氧基丙基酯、2,4,5-T-2-乙基己基酯、2,4,5-T-3-丁氧基丙基酯、2,4,5-TB、2,4,5-T-丁氧基丙酯(butometyl)、2,4,5-T-丁氧基乙基酯(2,4,5-T-butotyl)、2,4,5-T-丁基酯、2,4,5-T-異丁基酯、2,4,5-T-異辛基酯、2,4,5-T-異丙基酯、2,4,5-T-甲基酯、2,4,5-T-戊基酯、2,4,5-T-鈉、2,4,5-T-三乙基銨、2,4,5-T-三乙醇胺、2,4-D、2,4-D-2-丁氧基丙基酯、2,4-D-2-乙基己基酯、2,4-D-3-丁氧基丙基酯、2,4-D-銨、2,4-DB、2,4-DB-丁基酯、2,4-DB-二甲基銨、2,4-DB-異辛基酯、2,4-DB-鉀、2,4-DB-鈉、2,4-D-丁氧基乙基酯、2,4-D-丁基酯、2,4-D-二乙基銨、2,4-D-二甲基銨、2,4-D-二乙醇胺、2,4-D-十二基銨、2,4-DEB、2,4-DEP、2,4-D-乙基酯、2,4-D-庚基銨、2,4-D-異丁基酯、2,4-D-異辛基酯、2,4-D-異丙基酯、2,4-D-異丙基銨、2,4-D-鋰、2,4-D-異辛酯(meptyl)、2,4-D-甲基酯、2,4-D-辛基酯、2,4-D-戊基酯、2,4-D-鉀、2,4-D-丙基酯、2,4-D-鈉、2,4-D-四氫呋喃甲基酯(tefuryl)、2,4-D-十四基銨、2,4-D-三乙基銨、2,4-D-參(2-羥基丙基)銨、2,4-D-三乙醇胺、3,4-DA、3,4-DB、3,4-DP、4-CPA、4-CPB、4-CPP、乙草胺(acetochlor)、亞喜芬(acifluorfen)、甲基亞喜芬、亞喜芬鈉鹽(acifluorfen-sodium)、苯草醚(aclonifen)、丙烯醛
(acrolein)、拉草(alachlor)、二丙烯草胺(allidochlor)、亞汰草(alloxydim)、亞汰草鈉鹽、烯丙醇、亞羅列克(alorac)、胺酮(ametridione)、草殺淨(ametryn)、胺草酮(amibuzin)、胺唑草酮(amicarbazone)、醯嘧磺隆(amidosulfuron)、環丙嘧啶酸(aminocyclopyrachlor)、甲基環丙嘧啶酸、環丙嘧啶酸鉀鹽、氯胺吡啶酸(aminopyralid)、氯胺吡啶酸鉀鹽、氯胺吡啶酸-參(2-羥基丙基)銨鹽、甲基胺草磷(amiprofos)、殺草強(amitrole)、胺磺酸銨鹽、莎稗磷(anilofos)、安尼速隆(anisuron)、磺草靈(asulam)、磺草靈鉀鹽、磺草靈鈉鹽、阿特拉通(atraton)、草脫淨(atrazine)、草芬定(azafenidin)、四唑嘧磺隆(azimsulfuron)、滅蘇民(aziprotryne)、燕麥靈(barban)、BCPC、氟丁醯草胺(beflubutamid)、草除靈(benazolin)、草除靈二甲基銨鹽、乙基草除靈、草除靈鉀鹽、醯苯草酮(bencarbazone)、氟草胺(benfluralin)、呋草黃(benfuresate)、免速隆(bensulfuron)、甲基免速隆、地散磷(bensulide)、本達隆(bentazone)、本達隆鈉鹽、苯甲醯胺氧乙酸(benzadox)、苯甲醯胺氧乙酸銨鹽、雙苯嘧草酮(benzfendizone)、苄草胺(benzipram)、苯并雙環酮(benzobicyclon)、吡草酮(benzofenap)、氟草黃(benzofluor)、新燕靈(benzoylprop)、乙基新燕靈、苯噻隆(benzthiazuron)、雙環哌喃酮(bicyclopyrone)、治草醚(bifenox)、畢拉草(bilanafos)、畢拉草鈉鹽、雙草醚(bispyribac)、雙草醚鈉鹽、硼砂、克草(bromacil)、克草鋰
鹽、克草鈉鹽、除草溴(bromobonil)、溴丁醯草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、溴苯腈丁酸鹽、溴苯腈庚酸鹽、溴苯腈辛酸鹽、溴苯腈鉀鹽、溴莠敏(brompyrazon)、丁基拉草(butachlor)、布芬草(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、丁硫咪唑酮(buthidazole)、丁噻隆(buthiuron)、仲丁靈(butralin)、丁苯草酮(butroxydim)、炔草隆(buturon)、丁酸鹽、二甲胂酸(cacodylic acid)、苯酮唑(cafenstrole)、氯酸鈣、氰胺化鈣(calcium cyanamide)、卡本二氯(cambendichlor)、除草隆(carbasulam)、雙醯草胺(carbetamide)、羧酸唑(carboxazole)、克繁草(carfentrazone)、乙基克繁草(carfentrazone-ethyl)、CDEA、CEPC、甲氧基護谷(chlomethoxyfen)、克攔本(chloramben)、克攔本銨鹽、克攔本二乙醇胺鹽、甲基克攔本、克攔本甲基銨鹽、克攔本鈉鹽、丁醯草胺(chloranocryl)、炔禾靈(chlorazifop)、炔丙基炔禾靈(chlorazifop-propargyl)、氯阿淨(chlorazine)、滅落寧(chlorbromuron)、氯草靈(chlorbufam)、1-(3-氯-4-乙氧苯基)-3,3-二甲基脲(chloreturon)、伐草克(chlorfenac)、伐草克鈉鹽、燕麥酯(chlorfenprop)、甲基燕麥酯、氟咪殺(chlorflurazole)、整形醇(chlorflurenol)、甲基整形醇、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、乙基氯嘧磺隆、全滅草(chlornitrofen)、三氯丙酸(chloropon)、氯麥隆(chlorotoluron)、枯草龍(chloroxuron)、氯二甲酚
(chloroxynil)、氯普卡(chlorprocarb)、克普芬(chlorpropham)、氯磺隆(chlorsulfuron)、大克草(chlorthal)、二甲基大克草、單甲基大克草、草克樂(chlorthiamid)、乙基環醯草酯(cinidon)、環庚草醚(cinmethylin)、西速隆(cinosulfuron)、落草胺(cisanilide)、剋草同(clethodim)、2-氯-3,5-二碘吡啶-4-基乙酸酯(cliodinate)、炔草酯(clodinafop)、炔丙基炔草酯(clodinafop-propargyl)、2-[4-(4-氯苯氧基)苯氧基]丙酸(clofop)、異丁基2-[4-(4-氯苯氧基)苯氧基]丙酸、可滅蹤(clomazone)、克普草(clomeprop)、果美生長素(cloprop)、氯丙殺草(cloproxydime)、畢克草(clopyralid)、甲基畢克草、畢克草乙醇胺鹽(clopyralid-olamine)、畢克草鉀鹽、畢克草-參(2-羥基丙基)銨鹽、氯酯磺草胺(cloransulam)、甲基氯酯磺草胺、CMA、硫酸銅、CPMF、CPPC、必滅草(credazine)、甲酚(cresol)、草隆(cumyluron)、氰滿素(cyanamide)、氰草淨(cyanatryn)、氰乃淨(cyanazine)、環草敵(cycloate)、環磺隆(cyclosulfamuron)、環殺草(cycloxydim)、環莠隆(cycluron)、賽伏草(cyhalofop)、丁基賽伏草、牧草快(cyperquat)、牧草快氯鹽(cyperquat chloride)、環丙津(cyprazine)、三環噻草胺(cyprazole)、環草胺(cypromid)、汰草龍(daimuron)、得拉本(dalapon)、得拉本鈣鹽、得拉本鎂鹽、得拉本鈉鹽、邁隆(dazomet)、邁隆鈉鹽、異丁草胺(delachlor)、甜菜安(desmedipham)、敵草淨(desmetryn)、二醛酯(di-allate)、汰克草(dicamba)、汰
克草二甲基銨鹽、汰克草二乙醇胺鹽(dicamba-diolamine)、汰克草異丙基銨鹽、甲基汰克草、汰克草乙醇胺鹽、汰克草鉀鹽、汰克草鈉鹽、汰克草三乙醇胺鹽、二氯苯腈(dichlobenil)、雙(三氯羥乙基)脲(dichloralurea)、苄胺靈(dichlormate)、2,4-滴丙酸(dichlorprop)、2-乙基己基2,4-滴丙酸(dichlorprop-2-ethylhexyl)、2,4-滴丙酸丁氧基乙酯(dichlorprop-butotyl)、2,4-滴丙酸二甲基銨鹽、2,4-滴丙酸乙基銨鹽、異辛基2,4-滴丙酸、甲基2,4-滴丙酸、2,4-滴丙酸-P、2,4-滴丙酸-P-二甲基銨鹽、2,4-滴丙酸鉀鹽、2,4-滴丙酸鈉鹽、禾草靈(diclofop)、甲基禾草靈、雙氯磺草胺(diclosulam)、二依馬(diethamquat)、二依馬二氯鹽(diethamquat dichloride)、乙醯甲草胺(diethatyl)、乙基乙醯甲草胺、戊味禾草靈(difenopenten)、乙基戊味禾草靈、枯莠隆(difenoxuron)、野燕枯(difenzoquat)、野燕枯甲硫酸鹽(difenzoquat metilsulfate)、吡氟草胺(diflufenican)、氟吡草腙(diflufenzopyr)、氟吡草腙鈉鹽、唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、愛落殺(dimethametryn)、汰草滅(dimethenamid)、汰草滅-P、草滅散(dimexano)、草噠酮(dimidazon)、撻乃安(dinitramine)、地樂特(dinofenate)、硝丙酚(dinoprop)、戊硝酚(dinosam)、達諾殺(dinoseb)、乙酸達諾殺、達諾殺銨鹽、達諾殺二乙醇胺鹽(dinoseb-diolamine)、達諾殺鈉鹽、達諾殺三乙醇胺鹽、特樂酚(dinoterb)、乙酸特樂酚、得伐鼠
(diphacinone)鈉鹽、大芬滅(diphenamid)、異丙凈(dipropetryn)、大刈特(diquat)、大刈特二溴鹽、賽松(disul)、賽松鈉鹽、汰硫草(dithiopyr)、達有龍(diuron)、DMPA、DNOC、DNOC銨鹽、DNOC鉀鹽、DNOC鈉鹽、DSMA、EBEP、甘草津(eglinazine)、乙基甘草津、草多索(endothal)、草多索二銨鹽、草多索二鉀鹽、草多索二鈉鹽、三唑磺(epronaz)、EPTC、抑草蓬(erbon)、戊草丹(esprocarb)、乙丁烯氟靈(ethalfluralin)、胺苯磺隆(ethametsulfuron)、甲基胺苯磺隆、磺噻隆(ethidimuron)、硫草敵(ethiolate)、益覆滅(ethofumesate)、氯氟草醚(ethoxyfen)、乙基氯氟草醚、亞速隆(ethoxysulfuron)、硝草酚(etinofen)、益尼普滅(etnipromid)、乙氧苯草胺(etobenzanid)、EXD、雙氧威(fenasulam)、2,4,5-涕丙酸(fenoprop)、2,4,5-涕丙酸-3-丁氧基丙基(fenoprop-3-butoxypropyl)、2,4,5-涕丙酸-丁氧基丙酯(fenoprop-butometyl)、2,4,5-涕丙酸丁氧基乙酯(fenoprop-butotyl)、丁基2,4,5-涕丙酸、異辛基2,4,5-涕丙酸、甲基2,4,5-涕丙酸、2,4,5-涕丙酸鉀鹽、芬殺草(fenoxaprop)、乙基芬殺草、芬殺草-P、乙基芬殺草-P、異噁苯碸(fenoxasulfone)、2-(2,4,5-三氯苯氧基)乙醇(fenteracol)、噻唑禾草靈(fenthiaprop)、乙基噻唑禾草靈、四唑醯草胺(fentrazamide)、非草隆(fenuron)、非草隆TCA、硫酸亞鐵、麥草氟酯(flamprop)、異丙基麥草氟酯、麥草氟酯-M、甲基麥草氟酯、異丙基麥草氟酯-M、
甲基麥草氟酯-M、伏速隆(flazasulfuron)、雙氟磺草胺(florasulam)、伏寄普(fluazifop)、丁基伏寄普、甲基伏寄普、伏寄普-P、丁基伏寄普-P、異丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone)、氟酮磺隆鈉鹽、氟吡磺隆(flucetosulfuron)、貝殺寧(fluchloralin)、氟噻草胺(flufenacet)、弗芬肯(flufenican)、氟噠草酯(flufenpyr)、乙基氟噠草酯、闊草清(flumetsulam)、氟每淨(flumezin)、氟烯草酸(flumiclorac)、戊基氟烯草酸、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、可奪草(fluometuron)、福泰芬(fluorodifen)、乙羧氟草醚(fluoroglycofen)、乙基乙羧氟草醚、唑啶草(fluoromidine)、氟除草醚(fluoronitrofen)、殺克丹(fluothiuron)、氟胺草唑(flupoxam)、氟異丙嘧草酯(flupropacil)、氟丙酸(flupropanate)、氟丙酸鈉、氟啶嘧磺隆(flupyrsulfuron)、甲基氟啶嘧磺隆鈉鹽、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟氯比(fluroxypyr)、氟氯比丁氧基丙酯(fluroxypyr-butometyl)、氟氯比異辛酯(fluroxypyr-meptyl)、呋草酮(flurtamone)、氟噻草酯(fluthiacet)、甲基氟噻草酯、氟磺胺草醚(fomesafen)、氟磺胺草醚鈉鹽、甲醯胺磺隆(foramsulfuron)、調節膦(fosamine)、調節膦銨鹽、呋氧草醚(furyloxyfen)、草銨膦(glufosinate)、草銨膦銨鹽、草銨膦-P、草銨膦-P銨鹽、草銨膦-P鈉鹽、嘉磷塞(glyphosate)、嘉磷塞二銨、嘉磷塞二甲基銨、嘉磷塞異丙
基銨、嘉磷塞單銨鹽、嘉磷塞鉀、嘉磷塞倍半鈉(glyphosate-sesquisodium)、嘉磷塞三甲基硫鹽(glyphosate-trimesium)、鹵殺芬(halosafen)、合速隆(halosulfuron)、甲基合速隆、氟啶草(haloxydine)、合氯氟(haloxyfop)、合氯氟乙氧基乙酯(haloxyfop-etotyl)、甲基合氯氟、合氯氟-P、合氯氟-P乙氧基乙酯、甲基合氯氟-P、合氯氟鈉鹽、六氯丙酮(hexachloroacetone)、六氟鹽(hexaflurate)、菲殺淨(hexazinone)、咪草酸(imazamethabenz)、甲基咪草酸、咪草啶酸(imazamox)、咪草啶酸銨鹽、甲咪唑烟酸(imazapic)、甲咪唑烟酸銨鹽、依滅草(imazapyr)、依滅草異丙基銨鹽、滅草喹(imazaquin)、滅草喹銨鹽、甲基滅草喹、滅草喹鈉鹽、咪唑乙煙酸(imazethapyr)、咪唑乙煙酸銨鹽、依速隆(imazosulfuron)、茚草酮(indanofan)、三嗪茚草胺(indaziflam)、碘普尼(iodobonil)、碘甲烷、碘甲磺隆(iodosulfuron)、甲基碘甲磺隆鈉鹽、碘苯腈(ioxynil)、碘苯腈辛酸鹽(ioxynil octanoate)、碘苯腈鋰鹽、碘苯腈鈉鹽、抑草津(ipazine)、鹵苯胺唑(ipfencarbazone)、抑吡嘧丹(iprymidam)、草特靈(isocarbamid)、異草定(isocil)、丁草酮(isomethiozin)、異草完隆(isonoruron)、異丙林特(isopolinate)、異丙樂靈(isopropalin)、異丙隆(isoproturon)、愛速隆(isouron)、異草胺(isoxaben)、異氯草酮(isoxachlortole)、異唑草酮(isoxaflutole)、異草醚(isoxapyrifop)、特胺靈(karbutilate)、酮螺氧
(ketospiradox)、乳氟禾草靈(lactofen)、環草定(lenacil)、理有龍(linuron)、MAA、MAMA、MCPA、MCPA-2-乙基己基酯、MCPA丁氧基乙酯、MCPA-丁基酯、MCPA二甲基銨鹽、MCPA二乙醇胺鹽、MCPA-乙基酯、MCPA-異丁基酯、MCPA-異辛基酯、MCPA-異丙基酯、MCPA-甲基酯、MCPA乙醇胺鹽、MCPA鉀鹽、MCPA鈉鹽、MCPA-硫乙基酯(MCPA-thioethyl)、MCPA三乙醇胺鹽、MCPB、MCPB-乙基酯、MCPB-甲基酯、MCPB鈉鹽、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸-2-乙基己基酯(mecoprop-2-ethylhexyl)、2-甲-4-氯丙酸二甲基銨鹽、2-甲-4-氯丙酸二乙醇胺鹽、2-甲-4-氯丙酸-亞乙基酯(mecoprop-ethadyl)、2-甲-4-氯丙酸-異辛基酯、2-甲-4-氯丙酸-甲基酯、2-甲-4-氯丙酸-P、2-甲-4-氯丙酸-P二甲基銨鹽、2-甲-4-氯丙酸-P-異丁基酯、2-甲-4-氯丙酸鉀鹽、2-甲-4-氯丙酸-P鉀鹽、2-甲-4-氯丙酸鈉鹽、2-甲-4-氯丙酸三乙醇胺鹽、地樂施(medinoterb)、乙酸地樂施、滅芬草(mefenacet)、美福泰(mefluidide)、美福泰二乙醇胺鹽、美福泰鉀鹽、滅莠津(mesoprazine)、磺胺磺隆(mesosulfuron)、甲基磺胺磺隆、硝磺草酮(mesotrione)、斯美地(metam)、斯美地銨鹽、唑醯草胺(metamifop)、苯草酮(metamitron)、斯美地鉀鹽、斯美地鈉鹽、滅草胺(metazachlor)、雙醚氯吡嘧磺隆(metazosulfuron)、二甲噠草伏(metflurazon)、甲基苯噻隆(methabenzthiazuron)、甲基丙樂靈(methalpropalin)、滅草唑(methazole)、甲殺丹
(methiobencarb)、美西除靈(methiozolin)、滅草恆(methiuron)、醚草通(methometon)、格草净(methoprotryne)、溴甲烷、異硫氰酸甲酯、甲基殺草隆(methyldymron)、吡喃隆(metobenzuron)、莫多草(metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、滅必淨(metribuzin)、磺隆(metsulfuron)、甲基磺隆、稻得壯(molinate)、庚醯草胺(monalide)、莫尼速隆(monisouron)、一氯乙酸、綠谷龍(monolinuron)、滅草隆(monuron)、滅草隆TCA、伐草快(morfamquat)、伐草快二氯鹽、MSMA、萘普草(naproanilide)、滅落脫(napropamide)、納得爛(naptalam)、納得爛鈉鹽、草不龍(neburon)、煙嘧磺隆(nicosulfuron)、吡氯草胺(nipyraclofen)、滅殺草(nitralin)、護谷(nitrofen)、三氟甲草醚(nitrofluorfen)、氟草敏(norflurazon)、草完隆(noruron)、OCH、坪草丹(orbencarb)、鄰二氯苯、嘧苯胺磺隆(orthosulfamuron)、歐拉靈(oryzalin)、丙炔草酮(oxadiargyl)、樂滅草(oxadiazon)、草噠松(oxapyrazon)、草噠松(2-羥基乙基)二甲基銨鹽(oxapyrazon-dimolamine)、草噠松鈉鹽、環氧嘧磺隆(oxasulfuron)、草酮(oxaziclomefone)、復祿芬(oxyfluorfen)、對氟隆(parafluron)、巴拉刈(paraquat)、巴拉刈二氯鹽、巴拉刈硫酸二甲酯(paraquat dimetilsulfate)、克草猛(pebulate)、壬酸(pelargonic acid)、施得圃(pendimethalin)、平速爛(penoxsulam)、五氯酚(pentachlorophenol)、甲氯醯草胺
(pentanochlor)、環戊草酮(pentoxazone)、佈福松(perfluidone)、烯草胺(pethoxamid)、棉胺寧(phenisopham)、甜菜寧(phenmedipham)、甜菜寧-乙基酯(phenmedipham-ethyl)、醯草隆(phenobenzuron)、苯基乙酸汞(phenylmercury acetate)、畢克爛(picloram)、畢克爛-2-乙基己基酯(picloram-2-ethylhexyl)、畢克爛-異辛基酯、畢克爛-甲基酯、畢克爛乙醇胺鹽、畢克爛鉀鹽、畢克爛三乙基銨鹽、畢克爛-參(2-羥基丙基)銨鹽、氟吡醯草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、亞砷酸鉀(potassium arsenite)、疊氮化鉀(potassium arsenite)、氰酸鉀、普拉草(pretilachlor)、氟嘧磺隆(primisulfuron)、甲基氟嘧磺隆、環丙腈津(procyazine)、氨氟樂靈(prodiamine)、氟唑草胺(profluazol)、環丙氟靈(profluralin)、氯苯噻草酮(profoxydim)、甘撲津(proglinazine)、乙基甘撲津、撲滅通(prometon)、佈滅淨(prometryn)、雷蒙得(propachlor)、除草靈(propanil)、普拔草(propaquizafop)、普拔根(propazine)、苯胺靈(propham)、普樂寶(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆鈉鹽、咪唑嘧磺隆(propyrisulfuron)、戊炔草胺(propyzamide)、甲硫磺樂靈(prosulfalin)、苄草丹(prosulfocarb)、三氟丙磺隆(prosulfuron)、撲滅生(proxan)、撲滅生鈉鹽、吡達農(pydanon)、雙唑草腈(pyraclonil)、派芬草(pyraflufen)、乙基派芬草、磺醯草吡唑(pyrasulfotole)、苄草唑
(pyrazolynate)、百速隆(pyrazosulfuron)、乙基百速隆、匹唑芬(pyrazoxyfen)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、三氯吡啶醇(pyriclor)、噠草福(pyridafol)、必汰草(pyridate)、環酯草醚(pyriftalid)、嘧草醚(pyriminobac)、甲基嘧草醚、嘧啶硫蕃(pyrimisulfan)、嘧硫草醚(pyrithiobac)、嘧硫草醚鈉鹽、吡唑碸(pyroxasulfone)、快克草(quinclorac)、氯甲喹啉酸(quinmerac)、莫克草(quinoclamine)、克藻胺(quinonamid)、快伏草(quizalofop)、乙基快伏草、快伏草-P、乙基快伏草-P、四氫呋喃甲基快伏草-P(quizalofop-P-tefuryl)、硫氰苯胺(rhodethanil)、碸嘧磺隆(rimsulfuron)、嘧啶肟草醚(saflufenacil)、另丁津(sebuthylazine)、仲丁通(secbumeton)、西殺草(sethoxydim)、環草隆(siduron)、草滅淨(simazine)、西瑪通(simeton)、西草淨(simetryn)、SMA、左旋莫多草(S-metolachlor)、亞砷酸鈉、疊氮化鈉、氯酸鈉、磺草酮(sulcotrione)、草克死(sulfallate)、氟磺唑草胺(sulfentrazone)、嘧磺隆(sulfometuron)、甲基嘧磺隆、磺醯磺隆(sulfosulfuron)、硫酸、蘇葡卡賓(sulglycapin)、滅草靈(swep)、TCA、TCA銨鹽、TCA鈣鹽、TCA-亞乙基酯、TCA鎂鹽、TCA鈉鹽、牧草胺(tebutam)、得匍隆(tebuthiuron)、特呋三酮(tefuryltrione)、田寶三酮(tembotrione)、得殺草(tepraloxydim)、特草定(terbacil)、特草靈(terbucarb)、特丁草胺(terbuchlor)、特丁通
(terbumeton)、草凈津(terbuthylazine)、特丁淨(terbutryn)、四氟隆(tetrafluron)、欣克草(thenylchlor)、噻氟隆(thiazafluron)、噻草啶(thiazopyr)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、酮脲磺草吩酯(thiencarbazone)、甲基酮脲磺草吩酯、噻吩磺隆(thifensulfuron)、噻吩磺隆-甲基酯(thifensulfuron-methyl)、殺丹(thiobencarb)、仲草丹(tiocarbazil)、6-氯-5-(甲基硫代基)嘧啶-2,4-二胺(tioclorim)、吡草磺(topramezone)、三甲苯草酮(tralkoxydim)、燕麥畏(tri-allate)、醚苯磺隆(triasulfuron)、三氟草胺(triaziflam)、苯磺隆(tribenuron)、苯磺隆-甲基酯(tribenuron-methyl)、殺草畏(tricamba)、三氯比(triclopyr)、三氯比丁氧基乙酯(triclopyr-butotyl)、三氯比-乙基酯(triclopyr-ethyl)、三氯比三乙基銨鹽、三地芬(tridiphane)、草達津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆鈉鹽、三福林(trifluralin)、氟胺磺隆(triflusulfuron)、甲基氟胺磺隆、2-[4-[4-(三氟甲基)苯氧基]苯氧基]丙酸(trifop)、甲基2-[4-[4-(三氟甲基)苯氧基]苯氧基]丙酸、三氟禾草肟(trifopsime)、三羥基三、三甲隆(trimeturon)、三丙丹(tripropindan)、草達克(tritac)、三氟甲磺隆(tritosulfuron)、萬隆(vernolate),或是二甲苯草胺(xylachlor)。
該式I的化合物亦可以與一種或多種生物性殺蟲劑組合(諸如呈組成混合物之形式,或者同時或依序施用)。術語「生物性殺蟲劑」係用於施用方式與化學性殺蟲劑類似之微生物型生物性有害生物防治劑。通常,此等為細菌控制劑,但亦有真菌控制劑之實例,包括木黴屬(Trichoderma spp.)及白粉寄生孢(Ampelomyces quisqualis)(用於葡萄白粉病(grape powdery mildew)之控制劑)。枯草桿菌(Bacillus subtilis)用於控制植物病原體。雜草及嚙齒動物亦已用微生物劑控制。一種熟知的殺昆蟲劑實例係蘇力菌(Bacillus thuringiensis),其係一種鱗翅目(Lepidoptera)、鞘翅目(Coleoptera)及雙翅目(Diptera)之細菌性疾病。因為其對於其他生物體的效應極微,而被認為比合成殺蟲劑更具環境友善性。生物性殺昆蟲劑包括以下列為基礎之產物:1.昆蟲致病性真菌(如黑殭菌(Metarhizium anisopliae));2.昆蟲致病性線蟲(如蕪菁夜蛾斯氏線蟲(Steinernema feltiae));及3.昆蟲致病性病毒(如蘋果蠹蛾(Cydia pomonella)顆粒體病毒)。
昆蟲致病性生物體的其他實例包括但不限於桿狀病毒、細菌與其他原核生物體、真菌、原生動物及微孢子蟲(Microsproridia)。生物學衍生之殺昆蟲劑包括(但不限於)魚藤酮、藜蘆定鹼以及微生物毒素;耐昆蟲或抗昆蟲
之植物品種;以及藉由重組DNA技術修飾之生物體,從而產生殺昆蟲劑或賦予該基因改造型生物體抗昆蟲的性質。
在一具體例中,具式1的分子可與種子處理及土壤改良領域中的一或多種生物性殺蟲劑一起使用。The Manual of Biocontrol Agents對於可用的生物殺昆蟲劑(及其他生物式防治)產品進行綜合評論。Copping L.G.(編)(2004).The Manual of Biocontrol Agents(先前為the Biopesticide Manual)第3版.British Crop Production Council(BCPC),Farnham,Surrey UK。
該式I的化合物亦可以與下列中之一者或多者組合使用(諸如呈組成混合物之形式,或者同時或依序施用):1. 3-(4-氯-2,6-二甲基苯基)-4-羥基-8-氧-1-氮雜螺[4,5]癸-3-烯-2-酮(3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one);2. 3-(4'-氯-2,4-二甲基[1,1'-聯苯]-3-基)-4-羥基-8-氧-1-氮雜螺[4,5]癸-3-烯-2-酮;3. 4-[[(6-氯-3-吡啶基)甲基]甲基胺基]-2(5H)-呋喃酮;4. 4-[[(6-氯-3-吡啶基)甲基]環丙基胺基]-2(5H)-呋喃酮;5. 3-氯-N2-[(1S)-1-甲基-2-(甲基磺醯基)乙基]-N1-[2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]-1,2-苯二甲醯胺;6. 2-氰基-N-乙基-4-氟-3-甲氧基-苯磺醯胺;
7. 2-氰基-N-乙基-3-甲氧基-苯磺醯胺;8. 2-氰基-3-二氟甲氧基-N-乙基-4-氟-苯磺醯胺;9. 2-氰基-3-氟甲氧基-N-乙基-苯磺醯胺;10. 2-氰基-6-氟-3-甲氧基-N,N-二甲基-苯磺醯胺;11. 2-氰基-N-乙基-6-氟-3-甲氧基-N-甲基-苯磺醯胺;12. 2-氰基-3-二氟甲氧基-N,N-二甲基苯磺醯胺;13. 3-(二氟甲基)-N-[2-(3,3-二甲基丁基)苯基]-1-甲基-1H-吡唑-4-甲醯胺;14. N-乙基-2,2-二甲基丙醯胺-2-(2,6-二氯-α,α,α-三氟-對甲苯基)腙;15. N-乙基-2,2-二氯-1-甲基環丙烷-甲醯胺-2-(2,6-二氯-α,α,α-三氟-對甲苯基)腙菸鹼;16. O-{(E-)-[2-(4-氯-苯基)-2-氰基-1-(2-三氟甲基苯基)-乙烯基]}S-甲基硫碳酸酯;17. (E)-N1-[(2-氯-1,3-噻唑-5-基甲基)]-N2-氰基-N1-甲基乙脒;18. 1-(6-氯吡啶-3-基甲基)-7-甲基-8-硝基-1,2,3,5,6,7-六氫-咪唑并[1,2-a]吡啶-5-醇;19. 4-[4-氯苯基-(2-次丁基-亞肼基)甲基)]苯基甲磺酸酯;以及20. N-乙基-2,2-二氯-1-甲基環丙烷甲醯胺-2-(2,6-二氯-α,α,α-三氟-對甲苯基)腙。
該式I的化合物亦可以與下列群組中之一或多種化合物組合使用(諸如呈組成混合物之形式,或者同時或
依序施用):除藻劑、拒食劑、殺鳥劑(avicide)、殺菌劑、驅鳥劑、化學絕育劑、除草劑安全劑、誘蟲劑、驅蟲劑、驅哺乳動物劑、交配干擾劑、殺軟體動物劑、植物活化劑、植物生長調節劑、殺囓齒動物劑,或殺病毒劑。
該式I的化合物可以與至少一種其他的殺昆蟲劑組合使用,而形成協同性混合物,其中此等化合物的作用模式相比於該式I的化合物之作用模式,係相同、類似或是不同的。作用模式的實例可以包括但是不限於:乙醯膽鹼酯酶抑制劑;鈉通道調節劑;甲殼素生物合成抑制劑;GABA閘控氯化物通道拮抗劑;GABA及麩胺酸鹽閘控氯化物通道促效劑;乙醯膽鹼受體促效劑;MET I抑制劑;Mg刺激ATP酶抑制劑;菸鹼性乙醯膽鹼受體;中腸膜干擾劑;氧化磷酸化干擾劑,或是羅納丹受體(ryanodine receptor)(RyRs)。
此外,該式I的化合物可以與殺真菌劑、殺蜱蟎劑、除草劑或殺線蟲劑中至少一者組合使用,而形成協同性混合物。
而且,該式I的化合物可與其他活性化合物,諸如在“其他活性化合物”標題下的化合物、除藻劑、殺鳥劑、殺菌劑、殺軟體動物劑、殺囓齒動物劑、殺病毒劑、除草劑安全劑、佐劑及/或界面活性劑組合使用,而形成協同性混合物。此外,下列化合物係稱為協力劑及可與該式I的化合物組合使用:胡椒基丁氧化物、增效醛
(piprotal)、丙基增效劑(propyl isome)、增效菊(sesamex)、芝麻啉(sesamolin)、亞碸(sulfoxide)及脫葉磷(tribufos)。
殺蟲劑可能不適合以其純形式來施用。其通常需要添加其他物質,藉此該殺蟲劑能以促成方便施用、處理、輸送、儲存及最大殺蟲劑活性之所需濃度及適宜形式使用。因此,殺蟲劑可調配成例如餌劑、濃縮乳劑、粉劑、可乳化性濃縮液、燻蒸劑、膠劑、粒劑、微膠囊、種子處理劑、懸浮濃縮劑、懸乳劑(suspoemulsion)、片劑、水溶性液劑、水分散性粒劑或乾燥可流動劑、可濕性粉劑及超低體積溶液。關於調配物類型之進一步資訊,參見“Catalogue of Pesticide Formulation Types and International Coding System”Technical Monograph n°2,第5版CropLife International(2002)。
殺蟲劑最經常以由此等殺蟲劑的濃縮調配物所製備之含水懸浮液或乳劑的形式來施用。此等水溶性、水可懸浮或可乳化調配物為固體,通常稱為可濕性粉末或水可分散顆粒,或是液體,通常稱為可乳化濃縮物或水性懸浮液。可濕性粉末,其可經壓緊以形成水可分散顆粒,包含殺蟲劑、載劑及界面活性劑之緊密混合物。殺蟲劑之濃度通常為約10重量%至約90重量%。該載劑通常選自鎂鋁海泡石黏土(attapulgite clay)、蒙脫石黏土(montmorillonite clay)、矽藻土(diatomaceous earth)或純化矽酸鹽。構成約0.5%至約10%的可濕性粉劑之有效界面活性劑,係磺酸化
木質素、縮合萘磺酸鹽、萘磺酸鹽、烷基苯磺酸鹽、烷基硫酸鹽以及非離子性界面活性劑,諸如烷基苯酚的環氧乙烷加成物。
殺蟲劑之可乳化濃縮物包含溶解於載劑中合宜
濃度之殺蟲劑,諸如每公升液體約50至約500公克,該載劑為水可混溶的溶劑或水不混溶的有機溶劑及乳化劑之混合物。適用的有機溶劑包括芳族類,例如二甲苯類與石油分餾物,尤其是石油的高沸點萘與烯烴部分,諸如重芳族石油腦。亦可使用其他有機溶劑,諸如包括松香衍生物在內之萜烯溶劑、脂族酮類諸如環己酮,及複合醇類諸如2-乙氧基乙醇。用於可乳化性濃縮液之適宜乳化劑可以選自習用的陰離子性及非離子性界面活性劑。
水性懸浮液典型包含以在約5重量%至約50重量
%範圍內之濃度,分散在水性載劑中之非水溶性殺蟲劑的懸浮液。懸浮液藉由以下方式製備:精細研磨殺蟲劑並將其劇烈混合至載劑中,該載劑包含水及界面活性劑。亦可添加諸如無機鹽及合成膠或天然膠之成分,從而增加水性載劑之密度及黏度。通常最有效的為藉由在儀器,諸如砂磨機、球磨機或活塞型均質器,中製備水性混合物並對其進行均質化來同時研磨及混合殺蟲劑。
殺蟲劑亦可按顆粒組成物之形式來施用,該等
顆粒組成物尤其適用於施用至土壤中。顆粒組成物通常含有分散在載劑中之約0.5重量%至約10重量%之殺蟲劑,該載劑包含黏土或相似物質。該等組成物通常藉由以下方式
製備:將該殺蟲劑溶解在適合之溶劑中並將其施用至顆粒載劑上,該顆粒載劑已經預成形為適當粒徑,在約0.5至約3mm範圍內。該等組成物亦可藉由以下方式調配:將該載劑及化合物製成麵團狀或糊狀,且壓碎並乾燥,從而得到所需顆粒粒徑。
含有殺蟲劑之塵劑係藉由以下方式製備:將呈
粉末形式之殺蟲劑與適合之粉塵狀農業載劑,諸如高嶺黏土、經研磨火山岩及其類似載劑,緊密混合。塵劑可適合地含有約1%至約10%的殺蟲劑。其可施用作為種子敷料(seed dressing)或以粉塵鼓風機施用於葉片上。
同樣可行的為施用呈配於適當有機溶劑中的溶
液形式之殺蟲劑,該有機溶劑通常為石油諸如噴霧油,該有機溶劑廣泛用於農業化學。
殺蟲劑亦可以氣溶膠組成物之形式來施用。在
此等組成物中,將殺蟲劑溶解或分散在載劑中,該載劑為產生壓力之推進劑混合物。將氣溶膠組成物包裝在容器中,該混合物經由霧化閥而自該容器噴散。
當將殺蟲劑與食物或引誘劑或兩者混合時,形
成殺蟲劑誘餌。當害蟲吃掉誘餌時,其亦攝入殺蟲劑。誘餌可呈顆粒、凝膠、可流動粉末、液體或固體形式。其亦可用於害蟲藏身處。
薰蒸劑為具有相對較高蒸氣壓之殺蟲劑,且因
此可以濃度足以殺死土壤或密封空間中之害蟲的氣體形式存在。薰蒸劑之毒性與其濃度及曝露時間成比例。其等特
徵在於具有良好的擴散能力,並藉由滲透至害蟲之呼吸系統中或經由害蟲之表皮吸收而起作用。施用薰蒸劑以便在氣密房間或建築物中或在專門腔室中對防氣片(gas proof sheet)下之儲藏產品害蟲進行控制。
可藉由將殺蟲劑粒子或小滴懸浮在各種類型之
塑膠聚合物中,而將殺蟲劑微膠囊化。藉由改變聚合物之化學性質或藉由改變處理中之因素,可形成各種大小、溶解度、壁厚度及滲透度之微膠囊。此等因素控制其中活性成分之釋放速度,而釋放速度又影響產品之殘留效能、作用速度及氣味。
藉由將殺蟲劑溶於一溶劑,而該溶劑會將殺蟲
劑留置於溶液中,而製備油溶液濃縮物。殺蟲劑之油溶液由於溶劑本身具有殺蟲作用及體被之蠟質覆蓋物之溶解增加殺蟲劑的攝取速度,所以通常會提供比其他調配物更快的擊倒及殺死害蟲作用。油溶液之其他優點包括較好的儲藏穩定性、更好的裂縫滲透性及更好的油膩表面黏附性。
另一具體例包括水包油型乳劑,其中該乳劑包含油性小球,該等油性小球各自提供有層狀液晶塗層,並分散在水相中,其中各油性小球包含至少一種具有農業活性之化合物,並個別地塗佈有單層狀或寡層狀之層,該層包含:(1)至少一種非離子性親脂性界面活性劑,(2)至少一種非離子性親水性界面活性劑,及(3)至少一種離子性界面活性劑,其中該等小球具有小於800奈米之平均粒徑。關於具體例之其他資訊揭示於2007年2月1日公開,具有專
利申請案第11/495,228號之美國專利公開案20070027034中。為易於使用,此具體例將稱為「OIWE」。
關於其他資訊,查閱“Insect Pest Management”
第2版D.Dent,CAB International(2000)版權所有。此外,關於更詳細資訊,查閱“Handbook of Pest Control-The Behavior,Life History,and Control of Household Pests”Arnold Mallis,第9版,GIE Media Inc 2004版權所有。
一般而言,當該式I的化合物或其任一農業上可接受的鹽類用於一調配物中時,此調配物亦可含有其他組分。此等組分包括但不限於(其係一個非詳盡無遺及非互相排除的清單)濕潤劑、展佈劑、黏著劑、滲透劑、緩衝劑、螯合劑、漂浮降低劑、相容劑、消泡劑、清潔劑及乳化劑。現即說明一些組分。
潤濕劑係一物質,當添加至一液體時,藉由降低該液體與其展佈表面之間的界面張力而增加該液體的展佈或滲透力。潤濕劑用於農業化學調配物中之兩種主要功能:在處理及製造期間增加粉末在水中之潤濕速率從而製造可溶性液體之濃縮物或懸浮濃縮物;及在將產品與水在噴灑槽中混合期間降低可濕性粉末之潤濕時間,並使水滲透進入水可分散顆粒中的情況改善。用於可濕性粉末、懸浮濃縮物及水可分散顆粒調配物中的潤濕劑之實例為:月桂基硫酸鈉、二辛基磺基丁二酸鈉、烷基酚乙氧化物及脂族醇乙氧化物。
分散劑為吸附至粒子表面上並有助於保持粒子
之分散狀態以及防止粒子重新聚集的物質。將分散劑添加至農業化學調配物中以有助於製造期間之分散及懸浮,並且有助於確保粒子在噴灑槽中重新分散至水中。其廣泛用於可濕性粉末、懸浮濃縮物及水可分散顆粒中。用作分散劑之界面活性劑具有牢固吸附至粒子表面上之能力,並對粒子重新聚集提供電荷或空間障壁。最常用的界面活性劑為陰離子型、非離子型或該等兩種類型之混合物。對於可濕性粉末調配物,最常用分散劑為木質素磺酸鈉。對於懸浮濃縮物而言,使用聚電解質,諸如萘磺酸鈉甲醛濃縮物來得到極好的吸附及穩定。亦使用三苯乙烯基苯酚乙氧化物磷酸酯。非離子物,諸如烷基芳基氧化乙烯濃縮物及EO-PO嵌段共聚物,有時與陰離子物組合起來作為用於懸浮濃縮物之分散劑。近年來,新型式之極高分子量聚合物界面活性劑已開發作為分散劑。此等具有極長之疏水性『主鏈』及大量氧化乙烯鏈,其形成『梳狀』界面活性劑之『齒』。此等高分子量聚合物可對懸浮濃縮物產生極好的長期穩定性,因為疏水性主鏈對粒子表面具有許多錨定點。用於農業化學調配物之分散劑之實例為:木質素磺酸鈉;萘磺酸鈉甲醛濃縮物;三苯乙烯基苯酚乙氧化物磷酸酯;脂族醇乙氧化物;烷基乙氧化物;EO-PO嵌段共聚物;以及接枝共聚物。
乳化劑為使一種液相之液滴於另一液相中之懸
浮液穩定之物質。在無乳化劑之情況下,兩種液體會分離
成兩個不混溶的液相。最常用的乳化劑摻合物含有具有12個或12個以上環氧乙烷單元之烷基酚,或脂族醇及十二烷基苯磺酸之油溶性鈣鹽。8至18範圍的親水親油平衡(「HLB」)值通常將提供良好穩定之乳液。乳液穩定性有時可藉由添加少量EO-PO嵌段共聚物界面活性劑來改進。
增溶劑為在濃度超過臨界微胞濃度時,在水中
形成微胞之界面活性劑。接著,微胞能夠在微胞之疏水部分內溶解或使水不溶性物質溶解。通常用於溶解作用之界面活性劑類型為非離子型、脫水山梨糖醇單油酸酯、脫水山梨糖醇單油酸酯乙氧化物及油酸甲酯。
界面活性劑有時單獨使用,或與其他添加劑,
諸如作為佐劑之礦物油或植物油,一起使用於噴灑槽混合物,從而改進殺蟲劑對目標之生物效能。用於生物增強之界面活性劑類型通常視殺蟲劑之性質及作用模式而定。然而,其等通常為非離子物,諸如:烷基乙氧化物;線性脂族醇乙氧化物;脂族胺乙氧化物。
農業調配物中之載劑或稀釋劑為添加至殺蟲劑中以得到所需強度產品之物質。載劑通常為具有較高吸收能力之物質,而稀釋劑通常為具有較低吸收能力之物質。載劑及稀釋劑用於塵劑、可濕性粉末、顆粒及水可分散顆粒之調配物。
有機溶劑主要用於可乳化濃縮物、水包油乳液、懸乳劑及超低體積調配物之調配物,及在較少程度上用於顆粒調配物。有時,使用溶劑混合物。第一主要群組
之溶劑為脂族石蠟油,諸如煤油或精製石蠟。第二主要群組(且最常見)包含芳族溶劑,諸如二甲苯及較高分子量之C9及C10芳族溶劑之餾份。當將調配物乳化至水中時,氯化烴適用作防止殺蟲劑結晶之共溶劑。醇類有時用作共溶劑以增強溶解力。其他溶劑可包括植物油,種子油及植物油與種子油之酯類。
增稠劑或膠凝劑主要用於懸浮濃縮物、乳液及
懸乳劑之調配物,以改變液體之流變學或流動性質及防止分散粒子或液滴分離及沈降。增稠劑、膠凝劑及抗沈降劑通常屬於兩種類別,亦即水不溶性微粒及水溶性聚合物。
可使用黏土及二氧化矽來製造懸浮濃縮物調配物。此等物質類型之實例包括但不限於,蒙脫石、膨潤土、矽酸鎂鋁及鎂鋁海泡石。水溶性多醣多年來已用作增稠膠凝劑。最常用之多醣類型為種子及海藻之天然萃取物或纖維素之合成衍生物。此等類型物質之實例包括但不限於,瓜爾膠;刺槐豆膠;角叉菜膠;海藻酸鹽;甲基纖維素;羧甲基纖維素鈉(SCMC);羥乙基纖維素(HEC)。其他類型的抗沈降劑係基於改質澱粉、聚丙烯酸酯、聚乙烯醇及聚氧化乙烯。另一種良好的抗沈降劑為三仙膠。
微生物可引起經配製產品之損壞。因此,防腐
劑用於消除或降低其作用。該等試劑之實例包括但不限於:丙酸及其鈉鹽;山梨酸及其鈉或鉀鹽;苯甲酸及其鈉鹽;對羥基苯甲酸鈉鹽;對羥基苯甲酸甲酯;及1,2-苯并異噻唑啉-3-酮(BIT)。
界面活性劑之存在,經常造成水基調配物在製
造及經由噴灑槽施用時在混合操作期間起泡。為了減少起泡之傾向,通常在製造階段期間或裝填至瓶中之前,添加消泡劑。通常存在有兩種類型的消泡劑,亦即聚矽氧及非聚矽氧。聚矽氧通常為二甲基聚矽氧烷之水性乳液,而非聚矽氧消泡劑為水不溶性油,諸如辛醇及壬醇,或二氧化矽。在該兩種情況下,消泡劑之功能為自空氣-水界面中替換界面活性劑。
「綠色」製劑(例如佐劑、界面活性劑、溶劑)可
降低作物保護調配物之整體環境足跡。綠色試劑為生物可降解的,且通常衍生自天然及/或永續來源,例如植物及動物來源。特定實例為:植物油、種子油及其酯,以及烷氧基化烷基聚葡糖苷。
進一步的資訊請參見“Chemistry and Technology
of Agrochemical Formulations”,由D.A.Knowles編輯,Kluwer Academic Publishers 1998版權所有。亦參見“Insecticides in Agriculture and Environment-Retrospects and Prospects”,A.S.Perry,I.Yamamoto,I.Ishaaya及R.Perry,Springer-Verlag 1998版權所有。
此等所揭示之殺蟲組成物,可使用作為,例如殺線蟲劑、殺蜱蟎劑、殺蟲劑、殺昆蟲劑、殺蟎劑及/或殺軟體動物劑。
在一特定的具體例中,一種控制害蟲的方法包
含在害蟲種群附近,施用一殺蟲組成物,該殺蟲組成物包含式I的化合物或其任一農業上可接受的鹽類。
該式I的化合物通常以每公頃約0.01公克至每公
頃約5000公克之量使用以提供控制。通常較佳為每公頃約0.1公克至每公頃約500公克之量,且通常更佳為每公頃約1公克至每公頃約50公克之量。
該式I的化合物施用之區域可為害蟲居住(或可
能居住或經過)之任何區域,例如:作物、樹木、水果、穀類、飼料物種、藤本植物、草皮及觀賞植物生長處;家養動物居住處;建築物之內部或外部表面(諸如穀物儲存之位置)、建築物中使用之建築材料(諸如浸漬木材)及建築物周圍之土壤。使用式I分子之特定作物區域包括生長以下各者或將種植以下各者之種子的區域:蘋果、玉米、向日葵、棉花、大豆、芥花、小麥、稻米、高粱、大麥、燕麥、馬鈴薯、橙子、苜蓿、萵苣、草莓、番茄、胡椒、十字花科植物、梨、菸草、杏仁、甜菜、豆子以及其他有價值作物。在栽種各種植物之時,使用硫酸銨與該式I的化合物亦為有利的。
控制害蟲一般係指降低一區域之害蟲群體、害
蟲活動性或兩者。此可在如下情況時發生:害蟲群體自區域逐退;害蟲在區域內或在區域周圍無能力;或害蟲整體或部分在區域內或在區域周圍滅絕。當然,該等結果可組合發生。一般而言,害蟲群體、活動性或兩者希望降低超過50%,較佳超過90%。一般而言,該區域並非在一人類
體內或身上;因此,該位置一般為一個非人體區域。
該式I的化合物可以混合物的形式使用,同時施
用或依序施用、單獨施用或與其他增強植物活力(例如長出更好的根系、更能承受嚴苛的生長條件)之化合物一起施用。該等其他化合物為例如調節植物乙烯受體之化合物,最值得注意的為1-甲基環丙烯(亦稱為1-MCP)。另外,此等分子可在害蟲活動性較低期間使用,諸如在生長中之植物開始製造有價值之農產品之前。此等時間包括害蟲壓力通常較低時之早播季。
該式I的化合物可施用至植物之葉子及果實部分
以控制害蟲。該等分子將直接與害蟲接觸,或害蟲在食用含有殺蟲劑之葉子、果實或浸出汁液時吃掉該等殺蟲劑。
該式I的化合物亦可施用至土壤且當以此方式施用時,食用根及莖之害蟲可得以控制。根可吸收分子,將其吸取至植物之葉子部分以控制在地面上咀嚼及食用汁液之害蟲。
一般而言,在誘餌情況下,將誘餌置於例如白
蟻可與誘餌接觸及/或受其吸引之地面。亦可將誘餌施用至例如螞蟻、白蟻、蟑螂及蒼蠅可與誘餌接觸及/或受其吸引之建築物表面(水平、垂直或傾斜表面)。誘餌可包含該式I的化合物。
該式I的化合物可囊封在膠囊內、或置放於膠囊
表面上。膠囊的大小可在奈米大小(直徑大約100-900奈米)至微米大小(直徑大約10-900微米)範圍內。
由於一些害蟲之卵具有抗某些殺蟲劑之獨特能
力,故可能需要重複施用該式I的化合物以控制新出現之幼蟲。
可藉由在植物的不同部分施用(例如藉由噴灑一
區域)該式I的化合物,利用殺蟲劑在植物中的系統性移動,而控治位於植物另一部分的有害生物。舉例而言,例如,可藉由滴灌或條施,藉由以例如種植前或種植後之土壤澆灌而處理土壤,或藉由種植前處理植物種子來達成食葉昆蟲之控制。
可在將發芽之所有類型的種子進行種子處理,
包括經遺傳修飾以表現特殊性狀之植物的種子。代表性實例包括對無脊椎動物害蟲,諸如蘇力菌(Bacillus thuringiensis),表現蛋白毒性或其他殺昆蟲毒素者,表現除草劑抗性者,諸如「Roundup Ready」種子,或具有表現殺昆蟲毒素、除草劑抗性、營養增強、抗旱性或任何其他有益特性之「堆疊式」外來基因者。另外,該等使用該式I的化合物之種子處理可進一步增強植物耐嚴苛生長條件的能力。由此產生較健康,較有活力之植物,此在收穫時節可導致更高的產量。一般而言,預期每100,000個種子約1公克至約500公克之該式I的化合物提供良好益處,預期每100,000個種子約10公克至約100公克之量提供更佳益處,且預期每100,000個種子約25公克至約75公克之量提供甚至更佳益處。
應即可明瞭該式I的化合物可以用於經基因改造
以表現特殊性狀,諸如蘇力菌(Bacillus thuringiensis)或其
他殺昆蟲性毒素之植物,或是該等表現除草劑抗性者,或該等具有表現殺昆蟲性毒素、除草劑抗性、營養強化作用或其他任一有利性狀之「堆疊式」外來基因者之上、之中或周圍。
該式I的化合物可用於控制獸醫學領域或在非人
類動物飼養領域中之內寄生蟲及外寄生蟲。該式I的化合物諸如藉由以例如錠劑、膠囊、飲料、顆粒形式經口投與,藉由以例如浸泡、噴灑、傾倒、點藥及噴粉形式塗覆皮膚,及藉由以例如注射劑形式的非經腸投與來施用。
該式I的化合物亦可有利地用於家畜飼養,例如
牛、羊、豬、雞及鵝。其亦可有利地用於寵物,諸如馬、犬及貓。欲控制之特定害蟲將為會對該等動物造成麻煩之跳蚤及蜱。適合的調配物與飲用水或飼料一起經口投與該等動物。適合的劑量及調配物視物種而定。
該式I的化合物可用於控制寄生蟲,尤其是上列
動物腸道中的寄生蟲。該式I的化合物亦可用於人類健康照護之治療方法。該等方法包括但不限於,以例如錠劑、膠囊、飲料、顆粒形式經口投與及藉由皮膚施用。
全世界之害蟲正遷移至新環境(對於此害蟲而
言),且此後在該新環境中變成新的侵入物種。該式I的化合物亦可用於該等新的侵入物種,以在該新環境中對其進行控制。
該式I的化合物亦可用於植物,諸如作物,生長
(例如種植前、種植中、收穫前)之區域,以及可造成該等
植物的商業損失的有害生物水平低(甚至並無實際的存在)之區域。在該區域中使用該等分子會使在該區域中生長之植物受益。該等益處可包括但不限於,改進植物健康,改進植物產量(例如增加生物質及/或增加有價值成分之含量),改進植物活力(例如改進植物生長及/或更綠之葉子),改進植物品質(例如改進某些成分之含量或組成),及改進植物對非生物及/或生物脅迫之耐受性。
本揭示之包含該式I的化合物之殺蟲組成物可以
使用於控制廣泛種類的害蟲。
作為非限制性範例,在一個或多個具體例中,
本揭示之方法可用於控制下列中的一個或多個成員:蔬菜斑潛蠅(Liriomyza sativae)、巢針薊馬(Caliothrips phaseoli)、番茄木虱(Paratrioza cockerelli)、甜菜夜蛾(Spodoptera exigua)、桃蚜(Myzus persicae)、褐稻蝨(Nilaparvata lugens),以及煙草粉蝨(Bemisia tabaci)。
在額外的具體例中,本揭示之方法可用於控制
下列中至少一種之一個或多個成員:節肢動物門、圓形動物門、螯肢動物亞門、多足亞門、六足亞門、昆蟲綱、蛛形綱以及結閥綱。在至少一些具體例中,本發明之方法可用於控制昆蟲綱以及蛛形綱中至少一種之一個或多個成員。
於另外的具體例中,本揭示之方法可用於控制
鞘翅目(Order Coleoptera)(甲蟲)之成員,包括但不限於,豆象屬(Acanthoscelides spp.)(象鼻蟲)、菜豆象
(Acanthoscelides obtectus)(普通豌豆象鼻蟲)、白蠟窄吉丁(Agrilus planipennis)(花曲柳窄吉丁(emerald ash borer))、金針蟲屬(Agriotes spp.)(金針蟲(wireworm))、光肩星天牛(Anoplophora glabripennis)(亞洲長角天牛)、棉鈴象屬(Anthonomus spp.)(象鼻蟲)、墨西哥棉鈴象(Anthonomus grandis)(棉鈴象鼻蟲)、小繭蜂屬(Aphidius spp.)、長喙小象屬(Apion spp.)(象鼻蟲)、甘蔗金龜屬(Apogonia spp.)(蠐螬)、黑絨金龜(Ataenius spretulus)(黑絨金龜子(Black Turfgrass Ataenius))、甜菜隱食甲(Atomaria linearis)(小甜菜甲蟲(pygmy mangold beetle))、守瓜屬(Aulacophore spp.)、甜菜象(Bothynoderes punctiventris)(甜菜根象鼻蟲)、豆象屬(Bruchus spp.)(象鼻蟲)、豌豆象(Bruchus pisorum)(豌豆象鼻蟲)、Cacoesia屬(Cacoesia spp.)、四紋豆象(Callosobruchus maculatus)(南方豇豆象鼻蟲(southern cow pea weevil))、黄斑露尾甲(Carpophilus hemipteras)(乾果甲蟲)、甜菜龜金花蟲(Cassida vittata)、天牛屬(Cerosterna spp.)、葉甲蟲屬屬(Cerotoma spp.)(金花蟲(chrysomelids))、豆葉甲(Cerotoma trifurcata)(豆葉甲蟲)、龜象屬(Ceutorhynchus spp.)(象鼻蟲)、甘藍籽龜象(Ceutorhynchus assimilis)(甘藍莢象鼻蟲)、蕪菁龜象(Ceutorhynchus napi)(甘藍象鼻蟲(cabbage curculio))、跳甲屬(Chaetocnema spp.)(金花蟲(chrysomelids))、Colaspis屬(Colaspis spp.)(土甲蟲)、旋梯寬胸金針蟲(Conoderus scalaris)、多斑寬胸金針蟲(Conoderus stigmosus)、梅球頸
象(Conotrachelus nenuphar)(梅象鼻蟲(plum curculio))、Cotinus nitidis(綠花甲蟲(Green June beetle))、Crioceris asparagi(天門冬甲蟲)、銹赤扁榖盗(Cryptolestes ferruginous)(銹榖甲蟲)、長角扁榖盗(Cryptolestes pusillus)(扁榖甲蟲)、土耳其扁榖盗(Cryptolestes turcicus)(土耳其榖甲蟲)、旱地金針蟲屬(Ctenicera spp.)(金針蟲)、象鼻蟲屬(Curculio spp.)(象鼻蟲)、圓頭犀金龜屬(Cyclocephala spp.)(蠐螬)、密點細枝象(Cylindrocpturus adspersus)(向日葵莖象鼻蟲)、芒果切葉象甲(Deporaus marginatus)(芒果切葉象鼻蟲)、火腿皮蠹(Dermestes lardarius)(食物儲藏櫃甲蟲)、Dermestes maculates(白腹皮蠹(hide beetle))、根葉甲屬(Diabrotica spp.)(金花蟲(chrysomelids))、墨西哥豆瓢蟲(Epilachna varivcstis)(墨西哥豆甲蟲)、煙草鉆孑L蟲(Faustinus cubae)、蒼白樹皮象(Hylobius pales)(好鬥象鼻蟲(pales weevil))、葉象屬(Hypera spp.)(象鼻蟲)、Hypera postica(紫苜蓿象鼻蟲(alfalfa weevil))、Hyperdoes spp.(Hyperodes 象鼻蟲)、咖啡果小蠹(Hypothenemus hampei)(咖啡果甲蟲)、齒小蠹屬(Ips spp.)(雕刻小蠹(engravers))、鋸角毛竊蠹(Lasioderma serricorne)(烟草甲蟲)、科羅拉多金花蟲(Leptinotarsa decemlineata)(科羅拉多馬鈴薯甲蟲(Colorado potato beetle))、麗金龜(Liogenys fuscus)、Liogenys suturalis、稻根象(Lissorhoptrus oryzophilus)(稻水象鼻蟲)、粉蠹屬(Lyctus spp.)(木蠹蛾/粉蠹甲蟲(wood
beetles/powder post beetles))、Maecolaspis joliveti、美洲葉甲屬(Megascelis spp.)、玉米叩甲(Melanotus communis)、露尾甲屬(Meligethes spp.)、油菜花露尾甲(Meligethes aeneus)(花甲蟲)、大栗鰓角金龜子(Melolontha melolontha)(普通歐洲金龜(common European cockchafer))、梯頂天牛(Oberea brevis)、線形筒天牛(Oberea linearis)、椰虹犀金龜(Oryctes rhinoceros)(椰棗甲蟲)、粉扁蟲(Oryzaephilus mercator)(貿易榖盗甲蟲)、鋸胸粉扁蟲(Oryzaephilus surinamensis)(鋸齒榖甲蟲(sawtoothed grain beetle))、耳象屬(Otiorhynchus spp.)(象鼻蟲)、黑角負泥蟲(Oulema melanopus)(橙足負泥蟲(cereal leaf beetle))、稻負泥蟲(Oulema oryzae)、短喙象屬(Pantomorus spp.)(象鼻蟲)、鰓角金龜屬(Phyllophaga spp.)(五月/六月甲蟲)、金龜子(Phyllophaga cuyabana)(金花蟲(chrysomelids))、蘋虎象屬(Phynchites spp.)、日本麗金龜(Popillia japonica)(日本甲蟲)、Prostephanus truncates(大榖蠹(larger grain borer))、榖盗(Rhizopertha dominica)(榖蠹(lesser grain borer))、根觸金龜屬(Rhizotrogus spp.)(歐洲金龜子(European chafer))、大象鼻蟲屬(Rhynchophorus spp.)(象鼻蟲)、小蠹蟲屬(Scolytus spp.)(木蠹蛾(wood beetles))、Shenophorus spp.(榖象(Billbug))、豌豆根瘤象(Sitona lincatus)(豌豆葉象鼻蟲)、米象屬(Sitophilus spp.)(榖象鼻蟲(grain weevils))、榖象(Sitophilus granaries)(榖象鼻蟲(granary weevil))、米象(Sitophilus oryzae)(米象鼻蟲)、藥榖盗(Stegobium paniceum)(藥材甲蟲(drugstore beetle))、擬榖盗屬(Tribolium spp.)(麵粉甲蟲)、擬榖盗(Tribolium castaneum)(紅粉甲蟲)、扁擬榖盗(Tribolium confusum)(混亂麵粉甲蟲(confused flour beetle))、花斑皮蠹(Trogoderma variabile)(倉庫甲蟲),以及玉米距步甲蟲(Zabrus tenebioides)。
於其他的具體例中,本揭示之方法亦可用於控
制革翅目(Order Dermaptera)之成員(蠼螋(earwigs))。
在額外的具體例中,本揭示之方法可用於控制
蜚蠊目(Order Blattodea)(蟑螂)的成員,其包括但不限於,德國姬蠊(Blattella germanica)(德國蟑螂)、東方蜚蠊(Blatta orientalis)(東方蟑螂)、賓州稀蠊(Parcoblatta pennylvanica)、美洲家蠊(Periplaneta americana)(美國蟑螂)、澳洲家蠊(Periplaneta australoasiae)(澳洲蟑螂)、棕色家蠊(Periplaneta brunnea)(棕色蟑螂)、黑褐家蠊(Periplaneta fuliginosa)(棕色大蟑螂(smokybrown cockroach))、蘇里南蜚蠊(Pyncoselus suninamensis)(蘇里南蟑螂(Surinam cockroach)),以及長鬚帶蠊(Supella longipalpa)(棕帶蟑螂)。
於另外的具體例中,本揭示之方法可用於控制
雙翅目(Order Diptera)(蒼蠅(true flies))的成員,其包括但不限於,斑蚊屬(Aedes spp.)(蚊子)、寬額斑潛蠅(Agromyza frontella)(苜蓿斑潛葉蠅(alfalfa blotch leafminer))、潛蠅屬(Agromyza spp.)(斑潛蠅(leaf miner flies))、按實蠅屬
(Anastrepha spp.)(果蠅)、加勒比按實蠅(Anastrepha suspensa)(加勒比果蠅)、瘧蚊屬(Anopheles spp.)(蚊子)、果實蠅屬(Bactrocera spp.)(果蠅)、瓜實蠅(Bactrocera cucurbitae)(瓜實蠅(melon fly))、桔小實蠅(Bactrocera dorsalis)(東方果實蠅)、蠟實蠅屬(Ceratitis spp.)(果蠅)、地中海實蠅(Ceratitis capitata)(地中海果蠅(Mediterranean fruit fly))、斑虻屬(Chrysops spp.)(鹿虻)、錐蠅屬(Cochliomyia spp.)(螺旋蠅)、芽癭蚊屬(Contarinia spp.)(五倍子蠅(Gall midges))、家蚊屬(Culex spp.)(蚊子)、葉癭蚊屬(Dasineura spp.)(五倍子蠅(gall midges))、油菜葉癭蚊(Dasineura brassicae)(甘藍菜五倍子蠅)、艷粉蝶屬(Delia spp.)、歐洲花蠅(Delia platura)(玉米種蠅(seedcorn maggot))、果蠅屬(Drosophila spp.)(醋蠅)、廁蠅屬(Fannia spp.)(家蠅(filth flies))、黃腹廁蠅(Fannia canicularis)(小家廁蠅(little house fly))、灰腹廁蠅(Fannia scalaris)(廁蠅(latrine fly))、馬蠅(Gasterophilus intestinalis)(馬胃蠅)、Gracillia perseae、東方臂蠅(Haematobia irritans)(角蠅)、黑蠅屬(Hylemyia spp.)(根蛆(root maggots))、紋皮蠅(Hypoderma lineatum)(常見的牛蛆(common cattle grub))、斑潛蠅屬(Liriomyza spp.)(斑潛蚊(leafminer flies))、菜斑潛蠅(Liriomyza brassica)(螺痕斑潛蠅(serpentine leafminer))、羊蜱蠅(Melophagus ovinus)(綿羊蜱)、家蠅屬(Musca spp.)(蠅(muscid flies))、秋季家蠅(Musca autumnalis)(秋家蠅(face fly))、普通家蠅(Musca domestica)(家蠅)、嗜羊狂
蠅(Oestrus ovis)(羊狂蠅(sheep bot fly))、瑞典麥稈蠅(Oscinella frit)(小麥蟲(frit fly))、甜菜潛葉蠅(Pegomyia betae)(甜菜潛葉花蠅(beet leafminer))、草種蠅屬(Phorbia spp.)、胡蘿蔔蠅(Psila rosae)(胡蘿蔔蠅(carrot rust fly))、櫻桃線實蠅(Rhagoletis cerasi)(櫻桃實蠅(cherry fruit fly))、蘋果實蠅(Rhagoletis pomonella)(蘋果蛆(apple maggot))、紅吸漿蟲(Sitodiplosis mosellana)(麥紅吸漿蟲(orange wheat blossom midge))、畜廄刺蠅(Stomoxys calcitrans)(厩螯蠅(stable fly))、虻屬(Tabanus spp.)(馬蠅),以及大蚊屬(Tipula spp.)(大蚊(crane flies))。
於其他的具體例中,本揭示之方法可用於控制
半翅目(Order Hemiptera)(蝽(true bugs))的成員,其包括但不限於,綠蝽(Acrosternum hilare)(綠椿象(green stink bug))、麥長蝽(Blissus leucopterus)(麥小蝽(chinch bug)、馬鈴薯盲椿象(Calocoris norvegicus)(馬鈴薯盲蝽(potato mirid))、熱帶臭蟲(Cimex hemipterus)(熱帶臭蟲(tropical bed bug))、溫帶臭蟲(Cimex lectularius)(床虱(bed bug))、Dagbertus fasciatus、Dichelops furcatus、棉黑翅紅蝽(Dysdercus suturellus)(污棉蟲(cotton stainer))、Edessa meditabunda、扁盾蝽(Eurygaster maura)(榖物蟲(cereal bug))、英雄美洲蝽(Euschistus heros)、褐臭蝽(Euschistus servus)(棕色椿象(brown stink bug))、腰果刺盲蝽(Helopeltis antonii)、茶細蛾(Helopeltis theivora)(茶疫病盲蝽(tea blight plantbug))、稻椿象屬(Lagynotomus spp.)(椿象
(stink bugs))、大稻緣蝽(Leptocorisa oratorius)、稻緣椿象(Leptocorisa varicornis)、草盲蝽(Lygus spp.)(盲蝽(plant bugs))、豆莢草盲蝽(Lygus hesperus)(西部牧草盲蝽(western tarnished plant bug))、桑粉介殼蟲(Maconellicoccus hirsutus)、Neurocolpus longirostris、綠蝽(Nezara viridula)(南方綠椿象(southern green stink bug))、植盲椿象屬(Phytocoris spp.)(盲蝽)、加州葉盲蝽(Phytocoris californicus)、相對葉盲蝽(Phytocoris relativus)、蓋德擬壁蝽(Piezodorus guildinii)、四紋盲蝽(Poecilocapsus lineatus)(四線椿象(fourlined plant bug))、盲蝽(Psallus vaccinicola)、酪梨網蝽(Pseudacysta perseae)、土蝽(Scaptocoris castanea),以及錐獵蝽屬(Triatoma spp.)(吸血獵蝽/接吻蟲(bloodsucking conenose bugs/kissing bugs))。
在額外的具體例中,本揭示之方法可用於控制
同翅目(Order Homoptera)(蚜蟲類、蚧類、粉蝨類、葉蟬類)之成員,其包括但不限於,豌豆蚜(Acrythosiphon pisum)(豌豆蚜蟲)、球蚜屬(Adelges spp.)(球蚜(adelgids))、歐洲甘藍粉蝨(Aleurodes proletella)(甘藍粉蝨)、螺旋粉蝨(Aleurodicus disperses)、棉絮粉蝨(Aleurothrixus floccosus)(棉粉蝨(woolly whitefly))、白輪盾蚧屬(Aluacaspis spp.)、二點小綠葉蟬(Amrasca bigutella bigutella)、尖胸沫蟬屬(Aphrophora spp.)(葉蟬(leafhoppers))、橘紅腎圓盾介殼蟲(Aonidiella aurantii)(加州紅圓蚧(California red scale))、蚜
屬(Aphis spp.)(蚜蟲)、棉蚜(Aphis gossypii)(棉蚜蟲(cotton aphid))、蘋果蚜(Aphis pomi)(蘋果蚜蟲)、馬鈴薯蚜(Aulacorthum solani)(毛地黃蚜蟲(foxglove aphid))、伯粉蝨屬(Bemisia spp.)(粉蝨)、銀葉粉蝨(Bemisia argentifolii)、煙草粉蝨(Bemisia tabaci)(地瓜粉蝨)、麥雙尾蚜(Brachycolus noxius)(俄羅斯蚜蟲)、天門冬小管蚜(Brachycorynella asparagi)(蘆筍蚜蟲(asparagus aphid))、水稻粉紅粉介殼蟲(Brevennia rehi)、菜蚜(Brevicoryne brassicae)(甘藍蚜蟲)、蠟介屬(Ceroplastes spp.)(介殼蟲)、紅蠟介殼蟲(Ceroplastes rubens)(紅蠟介殼蟲(red wax scale))、雪盾介殼蟲屬(Chionaspis spp.)(介殼蟲)、褐圓盾介殼蟲屬(Chrysomphalus spp.)(介殼蟲)、介殼蟲屬(Coccus spp.)(介殼蟲)、車前草蚜(Dysaphis plantaginea)(蘋粉紅劣蚜(rosy apple aphid))、小綠葉蟬屬(Empoasca spp.)(葉蟬)、蘋果綿蚜(Eriosoma lanigerum)(蘋果棉蚜(woolly apple aphid))、吹棉介殼蟲(Icerya purchasi)(吹棉蚧(cottony cushion scale))、檬果褐葉蟬(Idioscopus nitidulus)(芒果葉蟬)、斑飛蝨(Laodelphax striatellus)(穗蝨(smaller brown planthopper))、蠣蚧屬(Lepidosaphes spp.)、毛茛芽屬(Macrosiphum spp.)、大戟長管蚜(Macrosiphum euphorbiae)(馬鈴薯蚜蟲)、麥長管蚜(Macrosiphum granarium)(英國五榖蚜蟲(English grain aphid))、薔薇長管蚜(Macrosiphum rosae)(玫瑰芽蟲)、四線葉蟬(Macrosteles quadrilineatus)(紫苑葉蟬(aster leafhopper))、沫蟬
(Mahanarva frimbiolata)、麥無網長管蚜(Metopolophium dirhodum)(薔薇麥蚜(rose grain aphid))、長角蝽象(Mictis longicornis)、瘤蚜屬(Myzus spp.)、桃蚜(Myzus persicae)(碧桃蚜蟲(green peach aphid))、黑尾葉蟬屬(Nephotettix spp.)(葉蟬)、黑尾葉蟬(Nephotettix cinctipes)(大青葉蟬(green leafhopper))、褐稻蝨(Nilaparvata lugens)(褐飛蝨(brown planthopper))、糠片盾蚧(Parlatoria pergandii)(糠介殼蟲(chaff scale))、黑片盾介殼蟲(Parlatoria ziziphi)(黑檀木介殼蟲(ebony scale))、玉米花翅飛虱(Peregrinus maidis)(玉米飛蝨(corn delphacid))、長沫蟬屬(Philaenus spp.)(沬蟬(spittlebugs))、根瘤蚜(Phylloxera vitifoliae)(葡萄根瘤蚜(grape phylloxera))、雲杉球蚧(Physokermes piceae)(雲杉芽介殼蟲(spruce bud scale)、動球菌屬(Planococcus spp.)(水蠟蟲(mealybugs))、粉介殼蟲屬(Pseudococcus spp.)(水蠟蟲(mealybugs))、菠蘿粉蚧(Pseudococcus brevipes)(鳳梨水蠟蟲(mealybugs))、梨圓盾蚧(Quadraspidiotus perniciosus)(梨圓盾介殼蟲(San Jose scale))、蚜蚧屬(Rhapalosiphum spp.)(蚜蟲)、玉米蚜(Rhapalosiphum maida)(玉米葉蚜蟲(corn leaf aphid))、稻麥芽(Rhapalosiphum padi)(黍縊蚜蟲(oat bird-cherry aphid))、黑盔蚧屬(Saissetia spp.)(介殼蟲)、工脊硬介殼蟲(Saissetia oleae)(黑色介殼蟲)、麥二叉蚜(Schizaphis graminum)(綠蚜)、麥長管芽(Sitobion avenae)(英國五榖蚜蟲)、白背褐蝨(Sogatella furcifera)(白背飛蝨(white-backed
planthopper))、彩斑蚜屬(Therioaphis spp.)(蚜蟲)、纹蠟蚧屬(Toumeyella spp.)(介殼蟲)、桔蚜屬(Toxoptera spp.)(蚜蟲)、棘粉蝨屬(Trialeurodes spp.)(粉蝨)、溫室粉蝨(Trialeurodes vaporariorum)(溫室粉蝨(greenhouse whitefly))、結翅白粉蝨(Trialeurodes abutiloneus)(結翅粉蝨(bandedwing whitefly))、矢盾介殼蟲屬(Unaspis spp.)(介殼蟲)、箭頭介殼蟲(Unaspis yanonensis)(箭頭介殼蟲(arrowhead scale))以及Zulia entreriana。在至少一些具體例中,本揭示之方法可用於控制桃蚜(Myzus persicae)。
於其他的具體例中,本揭示之方法可用於控制
膜翅目(Order Hymenoptera)(螞蟻、胡蜂以及蜜蜂)的成員,其包括但不限於,切葉蟻屬(Acromyrrmex spp.)、紅角菜葉蜂(Athalia rosae)、葉蟻屬(Atta spp.)(切葉蟻(leafcutting ants))、巨山蟻屬(Camponotus spp.)(木匠蟻)、松葉蜂屬(Diprion spp.)(鋸蜂(sawflies))、蟻屬(Formica spp.)(螞蟻)、阿根廷蟻(Iridomyrmex humilis)(阿根廷螞蟻(Argentine ant))、單家蟻屬(Monomorium ssp.)、小單家蟻(Monomorium minumum)(小黑蟻)、小黃單家蟻(Monomorium pharaonis)(法老蟻(Pharaoh ant))、新松葉蜂屬(Neodiprion spp.)(鋸蜂)、收獲蟻屬(Pogonomyrmex spp.)(收穫蟻(harvester ants))、馬蜂屬(Polistes spp.)(長腳蜂(paper wasps))、紅火蟻屬(Solenopsis spp.)(紅火蟻(fire ants))、酸臭家蟻(Tapoinoma sessile)(香家蟻(odorous house ant))、紅螞蟻屬(Tetranomorium spp.)(行道蟻)、黃胡蜂屬
(Vespula spp.)(胡蜂(yellow jackets))以及絨木蜂屬(Xylocopa spp.)(木蜂(carpenter bees))。
在某些具體例中,本揭示之方法可用於控制等
翅目(Order Isoptera)(白蟻)的成員,其包括但不限於,家白蟻屬(Coptotermes spp.)、大家白蟻(Coptotermes curvignathus)、法國白蟻(Coptotermes frenchii)、家白蟻(Coptotermes formosanus)(台灣乳白蟻(Formosan subterranean termite))、角象白蟻屬(Cornitermes spp.)(鼻形白蟻(nasute termites))、堆砂白蟻屬(Cryptotermes spp.)(乾木白蟻)、異白蟻屬(Heterotermes spp.)(沙漠地下蟻(desert subterranean termites))、金黃異白蟻(Heterotermes aureus)、木白蟻屬(Kalotermes spp.)(乾木白蟻)、切白蟻屬(Incistitermes spp.)(乾木白蟻)、大白蟻屬(Macrotermes spp.)(真菌栽培白蟻)、邊白蟻屬(Marginitermes spp.)(乾木白蟻)、鋸白蟻屬(Microcerotermes spp.)(草白蟻)、甘蔗白蟻(Microtermes obesi)、前角白蟻屬(Procornitermes spp.)、散白蟻屬(Reticulitermes spp.)(地下白蟻(subterranean termites))、班努斯散白蟻(Reticulitermes banyulensis)、草地散白蟻(Reticulitermes grassei)、黃肢散白蟻(Reticulitermes flavipes)(東方地下白蟻(eastern subterranean termite))、淺色南方散白蟻(Reticulitermes hageni)、美國散白蟻(Reticulitermes hesperus)(西方地下白蟻(western subterranean termite))、桑特散白蟻(Reticulitermes santonensis)、黃胸散白蟻(Reticulitermes speratus)、乾地
散白蟻(Reticulitermes tibialis)、南方散白蟻(Reticulitermes virginicus)、長鼻白蟻屬(Schedorhinotermes spp.)以及濕木白蟻屬(Zootermopsis spp.)(朽木白蟻(rotten-wood termites))。
在額外的具體例中,本揭示之方法可用於控制
鱗翅目(Order Lepidoptera)(蛾類以及蝴蝶)之成員,其包括但不限於,蓖麻螟蛉(Achoea janata)、茶姬捲葉蛾屬(Adoxophyes spp.)、棉褐帶捲葉蛾(Adoxophyes orana)、地老虎屬(Agrotis spp.)(切根蟲(cutworms))、小地老虎(Agrotis ipsilon)(黑切根蟲)、木棉蟲(Alabama argillacea)(棉葉蟲)、鱷梨捲葉蛾(Amorbia cuneana)、臍橙螟(Amyelosis transitella)(臍橙蟲(navel orangeworm))、褐影灰蛾(Anacamptodes defectaria)、桃枒蛾(Anarsia lineatella)(桃芽蛾(peach twig borer))、黃麻夜蛾(Anomis sabulifera)(黃麻尺蠖(jute looper))、大豆夜蛾(Anticarsia gemmatalis)(藜豆毛毛蟲(velvetbean caterpillar))、果樹黃捲蛾(Archips argyrospila)(果樹捲葉蛾(fruittree leafroller)、玫瑰黃捲蛾(Archips rosana)(玫瑰捲葉蛾(rose leaf roller)、帶捲蛾屬(Argyrotaenia spp.)(捲葉蛾(tortricid moths))、桔帶捲蛾(Argyrotaenia citrana)(甜橙捲葉蛾(orange tortrix))、γ纹夜蛾(Autographa gamma)、蘋果捲葉蛾(Bonagota cranaodes)、禾弄蝶(Borbo cinnara)(稻縱捲葉蟲(rice leaf folder))、棉潛蛾(Bucculatrix thurberiella)(棉潛夜蛾(cotton leafperforator))、麗細蛾屬(Caloptilia spp.)(潛葉蟲(leaf
miners))、織網衣蛾(Capua reticulana)、桃蛀果蛾(Carposina niponensis)(桃小食心蟲(peach fruit moth))、禾草螟屬(Chilo spp.)、横線尾夜蛾(Chlumetia transversa)(芒果夜蛾(mango shoot borer))、玫瑰帶紋捲葉蛾(Choristoneura rosaceana)(玫瑰色捲蛾(obliquebanded leafroller))、錁紋夜蛾屬(Chrysodeixis spp.)、瘤野螟(Cnaphalocerus medinalis)(禾草捲葉蛾(grass leafroller))、紋黃蝶屬(Colias spp.)、蒸枝受纹細蛾(Conpomorpha cramerella)、芳香木蠹蛾(Cossus cossus)(木蠹蛾(carpenter moth))、草螟屬(Crambus spp.)(草地螟(Sod webworms))、李小食心蟲(Cydiafunebrana)(李子果蛾(plum fruit moth))、梨小食心蟲(Cydia molesta)(梨小食心蛾(oriental fruit moth))、豆莢小捲蛾(Cydia nignicana)(豌豆蛀莢蛾(pea moth))、蘋果蠹蛾(Cydia pomonella)(蘋果蠹蛾(codling moth))、雙管刺蛾(Darna diducta)、絹野螟屬(Diaphania spp.)(鑽心蟲(stem borers))、桿草螟屬(Diatraea spp.)(蛀莖夜蛾(stalk borers))、小蔗桿草螟(Diatraea saccharalis)(蔗螟(sugarcane borer))、西南玉米桿草螟(Diatraea graniosella)(西南玉米螟)、金剛鑽屬(Earias spp.)(棉鈴蟲(bollworms))、埃及金剛鑽(Earias insulata)(埃及棉鈴蟲(Egyptian bollworm))、翠紋金剛鑽(Earias vitella)(棉鈴蟲(rough northern bollworm))、Ecdytopopha aurantianum、南美玉米苗斑螟(Elasmopalpus lignosellus)(小玉米莖蛀蟲(lesser cornstalk borer))、Epiphysias postruttana(淺棕色蘋果蛾(light brown apple moth))、粉斑螟屬(Ephestia spp.)(粉蛾)、粉斑螟蛾(Ephestia cautella)(粉斑螟(almond moth))、煙草粉斑螟(Ephestia elutella)(煙草天蛾)、地中海粉螟(Ephestia kuehniella)(地中海粉蛾(Mediterranean flour moth))、Epimeces屬(Epimeces spp.)、大豆捲葉蛾(Epinotia aporema)、尖翅蕉挵蝶(Erionota thrax)(蕉弄蝶(banana skipper))、女真細捲蛾(Eupoecilia ambiguella)(葡萄漿果蛾)、原切根蟲(Euxoa auxiliaris)(行軍切根蟲(army cutworm))、髒切葉蛾屬(Feltia spp.)(切根蟲)、角劍夜蛾屬(Gortyna spp.)(莖桿鑽心蟲(stemborers))、桃折心蟲(Grapholita molesta)(東方果實蛾(oriental fruit moth))、三紋螟蛾(Hedylepta indicata)(大豆捲夜螟(bean leaf webber))、和鈴夜蛾屬(Helicoverpa spp.)(夜蛾(noctuid moths))、棉蛉蟲(Helicoverpa armigera)(棉花暝蛉(cotton bollworm))、玉米穗蟲(Helicoverpa zea)(螟蛉/玉米穗蛾)、實夜蛾屬(Heliothis spp.)(夜蛾)、煙芽夜蛾(Heliothis virescens)(煙芽蟲(tobacco budworm))、菜心螟(Hellula undalis)(菜心螟(cabbage webworm))、根蠹屬(Indarbela spp.)(根莖天牛(root borers))、蕃茄莖麥蛾(Keiferia lycopersicella)(番茄蠹蛾(tomato pinworm))、茄黄斑螟(Leucinodes orbonalis)(螟蛾(eggplant fruit borer))、旋紋潛葉蛾(Leucoptera malifoliella)、細蛾屬(Lithocollectis spp.)、葡萄花翅小捲蛾(Lobesia botrana)(葡萄小捲蛾(grape fruit moth))、夜蛾屬(Loxagrotis spp.)(夜蛾(noctuid
moths))、西方豆夜盜蟲(Loxagrotis albicosta)(豆白緣切根蟲(western bean cutworm))、舞毒蛾(Lymantria dispar)(吉普賽飛蛾)、桃潛葉蛾(Lyonetia clerkella)(蘋果潛葉蛾)、科比特簑蛾(Mahasena corbetti)(油棕桐袋蛾(oil palm bagworm))、松毛蟲屬(Malacosoma spp.)(天幕毛蟲(tent caterpillars))、甘藍夜蛾(Mamestra brassicae)(甘藍行軍蟲)、豆莢螟(Maruca testulalis)(豆莢螟(bean pod borer))、平簑蛾(Metisa plana)(布袋蟲(bagworm))、栗夜盜蟲(Mythimna unipuncta)(栗夜盗蟲(true armyworm))、新野螟蛾(Neoleucinodes elegantalis)(小蕃茄食心蟲(small tomato borer))、稻三點螟(Nymphula depunctalis)(水稻螟蟲(rice caseworm))、冬蛾(Operophthera brumata)(冬尺蠖(winter moth))、歐洲玉米螟(Ostrinia nubilalis)(歐洲玉米螟(European corn borer))、大戟草尺蠖蛾(Oxydia vesulia)、葡萄褐捲蛾(Pandemis cerasana)(常見的醋栗捲葉蛾(common currant tortrix))、網紋褐捲葉蛾(Pandemis heparana)(蘋褐捲蛾(brown apple tortrix))、非洲達摩鳳蝶(Papilio demodocus)、棉紅鈴蟲(Pectinophora gossypiella)(棉紅蛉蟲(pink bollworm))、疆夜蛾屬(Peridroma spp.)(切根蟲)、雜色夜蛾(Peridroma saucia)(雜色夜蛾(variegated cutworm))、咖啡潛葉蛾(Perileucoptera coffeella)(白咖啡潛夜蛾(white coffee leafminer))、馬鈴薯蠹蛾(Phthorimaea operculella)(馬鈴薯塊莖蛾(potato tuber moth))、柑橘潛夜蛾(Phyllocnisitis citrella)、細蛾屬(Phyllonorycter spp.)(潛
夜蛾(leafminers))、紋白蝶(Pieris rapae)(菜青蟲(imported cabbageworm))、苜蓿綠夜蛾(Plathypena scabra)、印度穀螟蛾(Plodia interpunctella)(印度榖蛾(Indian meal moth))、小菜蛾(Plutella xylostella)(小菜蛾(diamondback moth))、葡萄果實小捲蛾(Polychrosis viteana)(葡萄捲葉蛾(grape berry moth))、桔果巢蛾(Prays endocarpa)、油橄欖巢蛾(Prays oleae)(油橄欖巢蛾(olive moth))、黏蟲屬(Pseudaletia spp.)(夜蛾)、一點黏蟲(Pseudaletia unipunctata)(行軍蟲)、大豆夜蛾(Pseudoplusia includens)(大豆尺蠖(soybean looper))、向日葵尺蠖(Rachiplusia nu)、三化螟(Scirpophaga incertulas)、蛀莖夜蛾屬(Sesamia spp.)(莖桿鑽蛀蟲)、稻蛀莖夜蛾(Sesamia inferens)(稻莖桿鑽蛀蟲(pink rice stem borer))、西非蛀莖夜蛾(Sesamia nonagrioides)、蕁麻毛蟲(Setora nitens)、麥蛾(Sitotroga cerealella)(麥蛾(Angoumois grain moth))、葡萄捲葉蛾(Sparganothis pilleriana)、夜盗蛾屬(Spodoptera spp.)(行軍蟲)、甜菜夜蛾(Spodoptera exigua)(甜菜夜蛾(beet armyworm))、秋夜盜蛾(Spodoptera fugiperda)(秋行軍蟲(fall armyworm))、南方灰翅夜蛾(Spodoptera oridania)(南方行軍蟲)、透翅蛾屬(Synanthedon spp.)(根莖天牛)、巴西里得小灰蝶(Thecla basilides)、Thermisia gemmatalis、袋衣蛾(Tineola bisselliella)(負袋夜蛾(webbing clothes moth))、粉紋夜蛾(Trichoplusia ni)(甘藍銀紋夜蛾(cabbage looper))、蕃茄夜蛾(Tuta absoluta)、巢蛾屬(Yponomeuta spp.)、咖啡豹蠹蛾
(Zeuzera coffeae)(red branch borer)以及梨豹蠹蛾(Zeuzera pyrina)(梨豹蠹蛾(leopard moth))。在至少一些具體例中,本發明之方法可用於控制甜菜夜蛾(Spodoptera exigua)。
本揭示之方法亦可用於控制(Order Mallophaga)
(嚼蝨(chewing lice))的成員,其包括但不限於,綿羊毛蝨(Bovicola ovis)(羊咬蝨(sheep biting louse))、雛雞羽蝨(Menacanthus stramineus)(雞體蝨(chicken body louse))以及雞羽蝨(Menopon gallinea)(常見母雞蝨子(common hen louse))。
在額外的具體例中,本揭示之方法可用於控制
直翅目(Order Orthoptera)(草蜢、蝗蟲以及蟋蟀)的成員,其包括但不限於,摩門螽斯(Anabrus simplex)(摩門蟋蟀(Mormon cricket))、螻蛄科(Gryllotalpidae)(螻蛄(mole crickets))、飛蝗(Locusta migratoria)、黑蝗屬(Melanoplus spp.)(草蜢)、稜翅螽斯(Microcentrum retinerve)(角翅蟈蟈(angularwinged katydid))、螽斯屬(Pterophylla spp.)(蟈蟈)、沙漠蝗(chistocerca gregaria)、叉尾灌叢樹螽(Scudderia furcata)(叉尾螽斯(forktailed bush katydid))以及Valanga nigricorni。
於其他的具體例中,本揭示之方法可用於控制
毛蝨目(Order Phthiraptera)(吸血蝨)的成員,其包括但不限於,獸蝨屬(Haematopinus spp.)(牛和豬的蝨子)、绵羊顎蝨(Linognathus ovillus)(綿羊蝨子)、頭蝨(Pediculus humanus capitis)(人類體蝨)、人體蝨(Pediculus humanus humanus)(人類體蝨)以及陰蝨(Pthirus pubis)(陰蝨(crab louse))。
在特定的具體例中,本揭示之方法可用於控制
蚤目(Order Siphonaptera)(跳蚤類)的成員,其包括但不限於,狗蚤(Ctenocephalides canis)(狗蚤(dog flea))、貓蚤(Ctenocephalides felis)(貓蚤(cat flea))以及人蚤(Pulex irritans)(人蚤(human flea))。
在額外的具體例中,本揭示之方法可用於控制
纓翅目(Order Thysanoptera)(薊馬(thrips))的成員,其包括但不限於,煙褐花薊馬(Frankliniella fusca)(菸草薊馬(tobacco thrips))、西方花薊馬(Frankliniella occidentalis)(西花薊馬(western flower thrips))、梳缺花薊馬(Frankliniella shultzei)、威廉斯花薊馬(Frankliniella williamsi)(玉米薊馬(corn thrips))、變葉木薊馬(Heliothrips haemorrhaidalis)(溫室薊馬)、腹鉤薊馬(Riphiphorothrips cruentatus)、跳薊馬屬(Scirtothrips spp.)、柑桔薊馬(Scirtothrips citri)(柑橘薊馬(citrus thrips))、小黃薊馬(Scirtothrips dorsalis)(黃茶薊馬(yellow tea thrips))、及帶薊馬(Taeniothrips rhopalantennalis),以及薊馬屬(Thrips spp.)。
本揭示之方法可用於控制纓尾目(Order
Thysanura)(無翼昆蟲(bristletails))的成員,其包括但不限於,衣魚屬(Lepisma spp.)(蠹魚(silverfish))以及小灶衣魚屬(Thermobia spp.)(家衣魚(firebrats))。
於另外的具體例中,本揭示之方法可用於控制
蜱蟎目(Order Acari)(蟎類以及蜱類)的成員,其包括但不限於,伍德氏蟎(Acarapsis woodi)(蜜蜂之氣管蟎(tracheal mite of honeybees))、粉蟎屬(Acarus spp.)(食物蟎)、粉塵蟎(Acarus siro)(榖蟎)、芒果癭瘤蟎(Aceria mangiferae)(芒果芽蟎(mango bud mite))、刺皮節蜱屬(Aculops spp.)、番茄刺皮癭蟎(Aculops lycopersici)(番茄葉刺皮癭蟎(tomato russet mite))、桔刺皮節蜱(Aculops pelekasi)、皮拉卡斯節蜱(Aculus pelekassi)、蘋果銹蜱(Aculus schlechtendali)(蘋果刺銹蟎(apple rust mite))、美洲花蜱(Amblyomma americanum)(孤星蜱(lone star tick))、牛壁蝨屬(Boophilus spp.)(壁蝨)、卵圓偽葉蟎(Brevipalpus obovatus)(卵形短鬚蟎(privet mite))、紫紅短鬚蟎(Brevipalpus phoenicis)(紅黑平蟎(red and black flat mite))、蠕形蟎屬(Demodex spp.)(疥蟎類(mange mites))、革蜱屬(Dermacentor spp.)(硬蜱(hard ticks))、變異革蜱(Dermacentor variabilis)(美洲狗蜱(american dog tick))、歐洲室塵蟎(Dermatophagoides pteronyssinus)(室塵蟎)、始葉蟎屬(Eotetranycus spp.)、鵝耳櫪始葉蟎(Eotetranychus carpini)(黃蜘蛛蟎)、上癭蟎屬(Epitimerus spp.)、節蜱屬(Eriophyes spp.)、硬蜱屬(Ixodes spp.)(壁蝨)、全爪蟎屬(Metatetranycus spp.)、貓節痂蟎(Notoedres cati)、赤葉蟎屬(Oligonychus spp.)、咖啡赤葉蟎(Oligonychus coffee)、伊氏赤葉蟎(Oligonychus ilicus)(冬青小爪蟎(southern red mite))、葉蟎屬(Panonychus spp.)、
柑橘葉蟎(Panonychus citri)(柑橘紅蟎(citrus red mite))、歐洲葉蟎(Panonychus ulmi)(歐洲紅蟎)、柑桔皺葉刺節蜱(Phyllocoptruta oleivora)(柑橘銹蟎)、多食細蟎(Polyphagotarsonemun latus)(廣明蟎(broad mite))、血紅扇頭蜱(Rhipicephalus sanguineus)(棕色犬蜱(brown dog tick))、扇頭蜱屬(Rhizoglyphus spp.)(根蟎(bulb mites))、人疥蟎(Sarcoptes scabiei)(疥蟎(itch mite))、鱷梨頂冠癭蟎(Tegolophus perseaflorae)、葉蟎屬(Tetranychus spp.)、二點葉蟎(Tetranychus urticae)(二點蜘蛛蟎(twospotted spider mite)),以及狄氏瓦蟎(Varroa destructor)(蜜蜂蟎)。
在額外的具體例中,本揭示之方法可用於控制
圓形動物門(Order Nematoda)(線蟲類)之成員,其包括但不限於,葉芽線蟲屬(Aphelenchoides spp.)(葉芽線蟲(foliar nematodes))、刺線蟲屬(Belonolaimus spp.)(刺線蟲(sting nematodes))、小環線蟲屬(Criconemella spp.)(環線蟲(ring nematodes))、犬心絲蟲(Dirofilaria immitis)(犬心絲蟲(dog heartworm))、莖線蟲屬(Ditylenchus spp.)(球蓮線蟲(stem and bulb nematodes))、包囊線蟲屬(Heterodera spp.)(包囊線蟲(cyst nematodes))、玉米包囊線蟲(Heterodera zeae)(玉米包囊線蟲(corn cyst nematode))、潛根線蟲屬(Hirschmanniella spp.)(根線蟲(root nematodes))、紐帶線蟲屬(Hoplolaimus spp.)(冠線蟲(lance nematodes))、根球線蟲屬(Meloidogyne spp.)(根結線蟲(root knot nematodes))、南方根結線蟲(Meloidogyne incognita)(根結線蟲)、盤尾線蟲
(Onchocerca volvulus)(鉤狀尾蟲(hook-tail worm))、根腐線蟲屬(Pratylenchus spp.)(根腐線蟲(lesion nematodes))、穿孔線蟲(Radopholus spp.)(穿孔線蟲(burrowing nematodes)),以及腎形線蟲(Rotylenchus reniformis)(腎形線蟲(kidney-shaped nematode))。
在至少一些具體例中,本揭示之方法可用於控
制下列目(Orders)中之一者或多者的至少一種昆蟲:鱗翅目(Lepidoptera)、鞘翅目(Coleoptera)、同翅目(Homoptera)、半翅目(Hemiptera)、纓翅目(Thysanoptera)、蜚蠊目(Blattodea)、等翅目(Isoptera)、直翅目(Orthoptera)、雙翅目(Diptera)、膜翅目(Hymenoptera)及蚤目(Siphonaptera),以及蜱蟎目(Order Acari)中的至少一種蟎。
碧桃蚜蟲(桃蚜(Myzus persicae))為桃樹最重要之蚜蟲害蟲,其導致生長減少、葉子枯萎及各種組織死亡。其亦因為作用為輸送植物病毒的載體而為有害,諸如將馬鈴薯病毒Y與馬鈴薯捲葉病毒(potato leafroll virus)輸送至顛茄/馬鈴薯科即茄科(nightshade/potato family Solanaceae)的成員,及將各種嵌紋病毒輸送至其他糧食作物。GPA害蟲所侵襲之此等植物的非限制性實例可以包括但不限於:青花菜、牛蒡、甘藍、胡蘿蔔、花椰菜、蘿蔔
(daikon)、茄子、青豆、萵苣、澳洲胡桃(macadamia)、木瓜、胡椒、甘薯、番茄、水芥(watercress)及西葫蘆(zucchini)以及其他植物。GPA害蟲亦可侵襲多種觀賞性作物,包括但不限於康乃馨、菊花、白花甘藍(flowering white cabbage)、一品紅及玫瑰。GPA已對於多種殺蟲劑產生抗藥性。
GPA之生物分析係準備如下:以種於3英吋
(7.62-cm)盆中及具有2至3片小(3至5公分)真葉的甘藍幼苗作為測試基材。在化學品施用前一天,用20-50隻GPA(成蟲及若蟲階段)侵害該等幼苗。針對各次處理使用四個具有個別幼苗之盆。將測試化合物(2mg)溶解於2mL丙酮/甲醇(1:1)溶劑中,形成1000ppm測試化合物之儲備溶液。
用含0.025% Tween® 20界面活性劑,其為聚氧乙烯(20)失水山梨醇單硬脂酸酯,之水溶液將儲備溶液稀釋5倍,得到200ppm測試化合物之溶液。用手持抽吸型噴霧器將溶液噴至甘藍葉子之兩面直至徑流。用僅含有20體積%丙酮/甲醇(1:1)溶劑之稀釋劑對對照植物(溶劑檢查)進行噴霧。
評級前,將經處理之植物在貯存室中在約25℃及環境相對濕度(RH)下置放三天。藉由在顯微鏡下計數每株植物上活蚜蟲之數目來進行評估。藉由使用如下所示之阿博特氏校正公式(Abbott's correction formula;W.S.Abbott,“A Method of Computing the Effectiveness of an Insecticide”,J.Econ.Entomol.18(1925),第265-267頁)來量測控制百分比。
經校正之控制%=100 * (X-Y)/X
其中X=溶劑檢查植物上之活蚜蟲數目,及Y=經處理植物上之活蚜蟲數目
結果在標題為「表2:碧桃蚜蟲(GPA)(MYZUPE)及地瓜粉蝨-爬蟲(WF)(BEMITA)之生物數據」中示出。所揭露的化合物之非限制性實例對抗對抗地瓜粉蝨-爬蟲(煙草粉蝨(Bemisia tabaci))(WF)(BEMITA)之殺昆蟲活性
地瓜粉蝨(煙草粉蝨(Bemisia tabaci))業已報導為全世界栽培作物的一種嚴重的害蟲。其有非常廣大的宿主範圍,侵襲超過63個科植物的500種物種。雜草通常作為作物害蟲替補的宿主。直接的取食損害是由刺破及吸吮植物的葉羣汁液所引致。此取食造成植物衰弱及提早凋萎,以及降低植物生長速率及產量。間接的損害係起源於粉蝨產生的甘露堆積。甘露用作為葉子與果實上黑煤病菌(black sooty mold)生長的基質,此會減少光合作用並使植物的市場價值或產量變少。在地瓜粉蝨媒介植物病毒時,亦會造成損害。地瓜粉蝨被認為是全世界植物病毒最常見且最重要的載體。
WF之葉羣噴灑分析係準備如下:於3英吋(7.62-cm)盆內生長具有1片小(4-5cm)真葉之棉花植物(陸地棉(Gossypium hirsutum))被作為測試基材。在化學品施用前4-5天,用200-400個粉蝨卵侵害該等植物。針對各次處理使用四個具有個別植物之盆。測試化合物(2毫克)溶於
1毫升丙酮溶劑,形成2000ppm之測試化合物的儲備溶液。儲備溶液以配於H2O(稀釋劑)中之0.025% Tween® 20界面活性劑予以稀釋10倍,以獲得200ppm之測試化合物的溶液。用手持抽吸型噴霧器將溶液噴至棉花葉子之兩面直至徑流。用僅含有10體積%丙酮溶劑之稀釋劑對對照植物(溶劑檢查)進行噴霧。評級前,將經處理之植物在貯存室中在約25℃及環境相對濕度(RH)下置放9天。藉由在顯微鏡下計數每株植物上活3-4若蟲之數目來進行評估。藉由使用如下所示之阿博特氏校正公式(Abbott's correction formula;W.S.Abbott,“A Method of Computing the Effectiveness of an Insecticide”,J.Econ.Entomol.18(1925),第265-267頁)來量測控制百分比。
經校正之控制%=100 * (X-Y)/X
其中X=溶劑檢查植物上之活若蟲數目,及Y=經處理植物上之活若蟲數目。
表2中指出結果。所揭示的殺蟲化合物對抗GPA與WF昆蟲之死亡率效率係依照表1中所示予以評等。
使用如上所述揭露的化合物之相同的測試程序,來測試比較化合物對抗GPA及WF害蟲之殺昆蟲活性。結果係如表3中所示。
如同中表1-3中所示,本揭示所揭露的化合物與比較化合物相比,顯示出對抗GPA及WF害蟲顯著改良的殺昆蟲活性。
下列實施例係用於更詳細的解釋本發明之具體例。此等實施例不應被解釋成本發明之全部範圍或是排他的範圍。
下列實施例係為了說明之目的,而不應解釋為將本揭示限制為僅此等實施例中揭露的具體例。
自商業來源獲得之起始原料、試劑及溶劑係未
經進一步純化即使用。無水溶劑係購自Aldrich之Sure/SealTM,及以所收到的形式使用。熔點係在Thomas Hoover Unimelt毛細管熔點儀或是在Stanford Research Systems之OptiMelt自動化熔點系統上測得,及未經校正。
使用「室溫」的實施例係在大約20℃至大約24℃的溫度之氣候控制實驗室中進行。分子係以其等依據ISIS Draw、ChemDraw或ACD Name Pro內的命名程式所命名之已知名稱顯示。若該等程式無法命名一分子,則該分子係依習用的命名規則來命名。1H NMR光譜數據係以ppm(δ)為單位及於300、400或600MHz記錄。13C NMR光譜數據係以ppm(δ)為單位及於75、100或150MHz記錄。19F NMR光譜數據係以ppm(δ)為單位及於376MHz記錄,除非另有說明。
於乾燥的圓底燒瓶(500mL)內,使3-肼吡啶二鹽酸鹽(4.02g,22.1mmol)、哌啶-2,4-二酮(2.50g,22.1mmol)及醋酸鈉(3.63g,44.2mmol)配於乾燥乙醇(196mL)
和水(24.56mL)中之混合物,於室溫下經磁力攪拌過夜。反應混合物蒸發至乾燥。殘餘物係用乙醇和甲苯來稀釋,以及接而於高真空下再次蒸發至乾燥,以提供4-(2-(吡啶-3-基)亞肼基)哌啶-2-酮,其使用於進一步合成不需純化。
將經磁力攪拌的4-(2-(吡啶-3-基)亞肼基)哌啶-2-酮(4.51g,22.1mmol)及二甲基甲醯胺‧二甲縮醛(83.0mL,618mmol)混合物,於氮氣下在圓底燒瓶(500mL)內,以回流加熱35分鐘。反應混合物蒸發至乾燥。殘餘物係用甲醇來稀釋,以及用矽來乾燥。生成的混合物於高真空下蒸發過夜至乾燥。粗物料係經由使用1-15%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如淺黃色固體之化合物F2(2.50g,50%)。
將1,1-二甲氧基-N,N-二甲基六亞甲基四胺(1,1-dimethoxy-N,N-dimethylmethanamine)(2.47mL,18.6mmol),添加至配於二甲基甲醯胺(70.7mL)之哌啶-2,4-二酮(2.00g,17.7mmol)溶液內。反應係於90℃下攪拌歷時4小時,接而於減壓下蒸發至乾燥,以提供如棕色油之化合物C1(3.17g,85%):1H NMR(300MHz,DMSO-d 6 )δ 7.94
(s,1H),3.24(s,2H),3.13(s,2H),2.87(s,3H),2.71(s,3H)。
將水合肼(hydrazine‧hydrate)(0.859mL,17.7
mmol),添加至配於乙醇(58.9mL)之(C1)(2.97g,17.7mmol)溶液內。讓反應回流歷時18小時,冷卻至室溫,然後於減壓下濃縮。粗物料係溶解於甲醇內且於矽藻土上濃縮。經由使用0-15%甲醇/二氯甲烷作為沖提液之急速管柱層析法純化,提供如黃色固體之化合物C2(0.816g,34%):1H NMR(400MHz,DMSO-d6)δ 13.01(s,1H),8.05(s,1H),7.31-7.19(m,1H),3.36(td,J=6.7,2.5Hz,2H),2.912.69(m,2H);ESIMS m/z 138([M+H]+)。
於0℃下將氫化鈉(60%配於油內,0.0320g,0.802mmol),添加至配於二甲基甲醯胺(7.29mL)之化合物C2(0.100g,0.729mmol)溶液內。於室溫下15分鐘之後,添加3-氟吡啶(0.0630mL,0.729mmol),以及於100℃下加熱歷時18小時。使反應冷卻至室溫,以及添加額外量的氫
化鈉(60%配於油內,0.0320g,0.802mmol)。於室溫下15分鐘之後,使反應於100℃下加熱歷時4小時,然後於120℃下加熱歷時19小時。反應係於減壓下濃縮。粗物料係經由使用0-100%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如灰白色固體之化合物F2(0.0400g,22%)。
於氮氣中、在0℃下將配於乾燥的四氫呋喃(2
mL)之(F2)(0.20g,0.93mmol),添加至配於乾燥的四氫呋喃(10mL)之氫化鈉(50%配於石蠟油,0.066g,1.4mmol)懸浮液。攪拌持續10分鐘之後,在0℃下逐滴地添加碘甲烷(0.13g,0.93mmol)。讓反應緩慢地回溫至室溫,以及於室溫下攪拌持續2至3小時。反應混合物係用飽和的氯化銨溶液(10mL)來驟冷,以及用乙酸乙酯(3 x 20mL)來萃取。組合的有機萃取物係用鹽水清洗,以及於無水硫酸鈉上乾燥。傾析的有機層係於減壓下蒸發至乾燥。粗產物係經由使用乙酸乙酯/己烷作為沖提液之急速管柱層析法予以純化,以提供如黃色固體之化合物F28(0.060g)。
下列分子係依據實施例5中揭示的程序來製造:
2-[4-側氧-2-(3-吡啶基)-6,7-二氫吡唑并[4,3-c]吡啶-5-基]乙腈(化合物F39)係使用2-溴乙腈來製備,以及單離為棕色固體(0.055g)。
配於乾燥的二甲基甲醯胺(35mL)之化合物F2
(0.700g,3.27mmol)、氫氧化鈉(1.30g,32.7mmol)以及環丙基甲基溴(4.41g,32.7mmol)的懸浮液,係於室溫下攪拌歷時18小時。反應係用乙酸乙酯(75mL)予以稀釋,以及接而用水(3 x 50mL)和鹽水(50mL)來清洗。反應溶液係於無水的硫酸鈉上乾燥、過濾且於減壓下濃縮蒸發至乾
燥。殘餘物係經由使用乙酸乙酯/己烷作為沖提液之急速管柱層析法予以純化,以提供如黃色固體之化合物F1(0.030g,24%)。
下列分子係依據實施例7中揭示的程序來製造:
5-異丙基-2-(3-吡啶基)-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F6)係使用2-碘丙烷來製備,以及單離為一種膠(0.180g,22%)。
使用實施例7中揭示的程序,5-[2-(4-環丁基哌-1-基)-2-側氧-乙基]-2-(3-吡啶基)-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F42)係利用2-氯-1-(4-環丁基哌-1-基)ethanone(WO 200/7016496)來製備,以及單離為一種灰白色固體(0.070g,19%)。
於0℃下將氫化鈉(60%配於油內,0.0220g,0.560mmol),添加至配於二甲基甲醯胺(4.67mL)之化合物F2(0.100g,0.467mmol)溶液內。於0℃下10分鐘及室溫下15分鐘之後,使反應冷卻至0℃,並添加溴化烯丙基(0.0570mL,0.654mmol)。於0℃下10分鐘之後,讓反應於室溫下攪拌歷時3.5小時,隨之用鹽水稀釋,以及用乙酸乙酯來萃取。組合的有機相係用鹽水清洗,於硫酸鎂上乾燥,以及濃縮。殘餘物係經由使用0-15%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如黃色固體之化合物31(0.0600g,50%)。
下列分子係依據實施例10中揭示的程序來製造:
使用實施例10中揭示的程序,5-(甲基磺醯基甲
基)-2-(3-吡啶基)-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F20)係利用(氯甲基)(甲基)硫烷((chloromethyl)(methyl)sulfane)來製備,以及單離為一種黃色固體(0.029g,22%)。
使用實施例10中揭示的程序,甲基2-[4-側氧
-2-(3-吡啶基)-6,7-二氫吡唑并[4,3-c]吡啶-5-基]乙酸酯(化合物F30)係利用2-溴乙酸甲酯來製備,以及單離為一種黃色固體(0.166g,24%)。
於氮氣下將乾燥小瓶(25mL)中的氫化鈉(60%配於油內,0.0205g,0.513mmol),添加至配於乾燥二甲基
甲醯胺(2mL)之經磁力攪拌的化合物F2(0.100g,0.467mmol)混合物內。反應混合物係於室溫下攪拌歷時10分鐘,然後添加1-(溴甲基)-2-氟苯(0.106g,0.560mmol),以及讓混合物於室溫下攪拌過夜。反應混合物係用冰冷的水/氯化氫(2N)來稀釋,以及用二氯甲烷予以萃取二次。使組合的二氯甲烷萃取物蒸發,以及粗物料係藉由逆相高壓液相層析法(Gilson-1 Column-Atlantis Prep;T3 5um OBD 30 X 100mm;流速-29.15mL/分鐘;梯度-(10至70%)乙腈及水加上0.1%乙酸)予以純化,以提供如灰白色固體之化合物F17(0.030g,19%)。
下列分子係依據實施例13中揭示的程序來製造:
2-(3-吡啶基)-5-[[2-(三氟甲基)苯基]甲基]-6,7-二
氫吡唑并[4,3-c]吡啶-4-酮(化合物F32)係利用1-(溴甲基)-2-(三氟甲基)苯來製備,以及單離為一種灰白色固體(0.078g,43%)。
5-[(4-甲氧基苯基)甲基]-2-(3-吡啶基)-6,7-二氫
吡唑并[4,3-c]吡啶-4-酮(化合物F23)係利用1-(氯甲基)-4-甲氧基苯來製備,以及單離為一種灰白色固體(0.049g,30%)。
使用實施例13中揭示的程序,2-(3-吡啶
基)-5-[[3-(三氟甲基)苯基]甲基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F29)係利用1-(氯甲基)-3-(三氟甲基)苯來製備,以及單離為一種灰白色固體(0.0056g,56%)。
於氮氣下將乾燥小瓶(5mL)中的雙(三甲矽)醯胺
化鋰(1M配於甲苯,0.26mL,0.26mmol),添加至配於乾燥二甲基甲醯胺(1.2mL)之經磁力攪拌的化合物F2(0.050g,0.23mmol)混合物內。反應混合物係於室溫下攪拌歷時5分鐘。然後添加1-(溴甲基)-4-氟苯(0.034mL,0.28mmol),以及讓反應混合物於室溫下攪拌過夜。反應混合物係用冰冷的水/氯化氫(2N)來稀釋,以及用二氯甲烷予以萃取二次。使組合的二氯甲烷萃取物蒸發,以及粗物料係藉由逆相高壓液相層析法(Gilson-1 Column-Atlantis Prep;T3 5um OBD 30 X 100mm;流速-29.15mL/分鐘;梯度-(10至90%)乙腈及水加上0.1%乙酸)予以純化,以提供如白色固體之化合物F3(0.0047g,6%)。
下列分子係依據實施例17中揭示的程序來製造:
2-(3-吡啶基)-5-[[4-(三氟甲基)苯基]甲基]-6,7-二
氫吡唑并[4,3-c]吡啶-4-酮(化合物F50)係利用1-(氯甲基)-4-(三氟甲基)苯來製備,以及單離為一種白色的固體(0.0501g,55%)。
使用實施例17中揭示的程序,5-[(2-甲氧基苯基)
甲基]-2-(3-吡啶基)-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F15)係利用1-(氯甲基)-2-甲氧基苯來製備,以及單離為一種黃色的蠟(0.0337g,41%)。
於氮氣下,在乾燥的圓底燒瓶(50mL)內,將配
於乾燥的二甲基甲醯胺(11mL)之化合物F2(0.500g,2.33mmol)及乾燥的六甲基磷酸三胺(1mL)之磁力攪拌的混合物,於室溫下攪拌直到全部起始原料溶解為止,接而冷卻至冰浴溫度,以及添加雙(三甲矽)醯胺化鋰(1M配於甲苯,2.33mL,2.33mmol)。淺黃色反應混合物變成深橘色,以及於冰浴溫度攪拌5分鐘。添加2-氯乙酸乙酯(0.500mL,4.67mmol),以及攪拌反應混合物30分鐘。反應混合物係用冰水及幾滴氯化氫(2N)來稀釋。內含物係進一步用二氯甲烷及含水碳酸氫鈉予以稀釋,以及將層分離。使有機萃取物蒸發,以及經由使用0、5、10%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如黃色固體之化合物F8(0.408g,55%)。
將3-(甲硫基)丙醯氯(0.142g,1.03mmol)及N-乙
基-N-異丙基丙-2-胺(0.179mL,1.03mmol),添加至配於
1,2-二氯乙烷(1.87mL)之化合物F2(0.100g,0.467mmol)溶液內。將反應小瓶加蓋,以及於具有外部IR-感測器溫度監測之CEM Discover之微波反應器中,從小瓶的底部以100℃予以加熱反應歷時3小時。將溶液放置於分液漏斗之內。添加飽和的含水碳酸氫鈉,以及用乙酸乙酯來萃取混合物。將有機萃取物予以組合、於硫酸鎂上乾燥及濃縮。
殘餘物係經由使用0-15%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如黃色油之標題化合物F12(0.011g,7%)。
將2-溴吡啶(0.043mL,0.45mmol)、碳酸銫
(0.24g,0.75mmol)、碘化銅(I)(3.6mg,0.019mmol)以及反式-1,2-二胺基環己烷(0.0045mL,0.037mmol),添加至配於二噁烷(dioxane)(3.7mL)之化合物F2(0.080g,0.37mmol)溶液之內。反應係於氮氣下以回流來加熱歷時15小時,使反應冷卻至室溫,用鹽水予以稀釋,以及用乙酸乙酯來萃取。組合的有機相係於硫酸鎂上乾燥以及濃縮。殘餘物係藉由使用0-15%甲醇/二氯甲烷作為沖提液之急速管
柱層析法予以純化,以提供如米黃色的固體之化合物F43(0.052g,47%)。
將2-溴-5-(三氟甲基)吡啶(0.063g,0.28
mmol)、4,5-雙(二苯膦)-9,9-二甲基(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)(Xantphos)(0.0068g,0.012mmol),和碳酸銫(0.11g,0.35mmol),添加至配於二噁烷(2.3mL)之化合物F2(0.050g,0.23mmol)溶液之內。反應係於氮中除氣且添加三(二亞苄基丙酮)二鈀(0)(0.0021g,0.0023mmol)。反應係於120℃下加熱歷時6小時。使反應冷卻至室溫,用鹽水稀釋,以及用乙酸乙酯來萃取。組合的有機相係於硫酸鎂上乾燥以及濃縮。殘餘物係經由使用0-15%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如白色固體之化合物F37(0.069g,82%)。
下列分子係依據實施例23中揭示的程序來製造:
2-(3-吡啶基)-5-[6-(三氟甲基)-2-吡啶基]-6,7-二
氫吡唑并[4,3-c]吡啶-4-酮(化合物F46)係利用2-溴-6-(三氟甲基)吡啶來製備,以及單離為一種白色的固體(0.054g,64%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-(6-嘧啶-2-基-2-吡啶基)-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F38)係利用2-(6-溴吡啶-2-基)嘧啶來製備,以及單離為一種淡黃色固體(0.108g,83%)。
使用實施例23中揭示的程序,2-(3-吡啶基)-5-嘧
啶-2-基-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F34)係利用2-
氯嘧啶來製備,以及單離為一種黃色固體(0.016g,23%)。
使用實施例23中揭示的程序,5-(6-甲氧基-2-吡
啶基)-2-(3-吡啶基)-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F18)係利用2-溴-6-甲氧基吡啶來製備,以及單離為一種淡黃色固體(0.039g,52%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-[4-(三氟甲基)-2-吡啶基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F7)係利用2-溴-4-(三氟甲基)吡啶來製備,以及單離為一種黃色固體(0.044g,53%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-[3-(三氟甲氧基)苯基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F22)係利用1-溴-3-(三氟甲氧基)苯來製備,以及單離為一種黃色固體(0.046g,53%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-[3-(三氟甲基)-2-吡啶基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F10)係利用2-溴-3-(三氟甲基)吡啶來製備,以及單離為一種黃色的油(0.018g,21%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-[5-(三氟甲基)-3-吡啶基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F21)係利用3-溴-5-(三氟甲基)吡啶來製備,以及單離為一種黃色固體(0.0182g,21%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-[6-(三氟甲基)嘧啶-4-基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F48)係利用4-溴-6-(三氟甲基)嘧啶來製備,以及單離為一種淺棕色固體(0.0553g,63%)。
使用實施例23中揭示的程序,5-(5-氟-2-吡啶
基)-2-(3-吡啶基)-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F49)係利用2-溴-5-氟吡啶來製備,以及單離為一種黃色固體(0.0275g,36%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-[4-(三氟甲基)苯基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F13)係利用1-溴-4-(三氟甲基)苯來製備,以及單離為一種黃色固體(0.0169g,19%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-[4-(三氟甲氧基)苯基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F14)係利用1-溴-4-(三氟甲氧基)苯來製備,以及單離為一種黃色固體(0.036g,39%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-[2-(三氟甲基)-4-吡啶基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F5)係利用4-溴-2-(三氟甲基)吡啶來製備,以及單離為一種深黃色固體(0.0552g,63%)。
使用實施例23中揭示的程序,2-(3-吡啶
基)-5-[6-(三氟甲基)-3-吡啶基]-6,7-二氫吡唑并[4,3-c]吡啶-4-酮(化合物F33)係利用5-溴-2-(三氟甲基)吡啶來製備,以及單離為一種黃色固體(0.0161g,16%)。
2-(3-吡啶基)-5-[3-(三氟甲基)苯基]-6,7-二氫吡
唑并[4,3-c]吡啶-4-酮(化合物F4)係利用1-溴-3-(三氟甲基)苯來製備,以及單離為一種黃色的固體(0.0519g,56%)。
於氮氣下,將乾燥小瓶(50mL)中的硼氫化鈉
(0.083g,2.2mmol),添加至配於乾燥乙醇(7.3mL)之經磁力攪拌的化合物F8(0.066g,2.2mmol)混合物內。反應混合物係於室溫下攪拌過夜。反應混合物係用冰水稀釋,以及用氯化氫(2N)來將pH調整至中性。生成的混合物蒸發至乾燥。粗製固體係用二氯甲烷/乙醇予以萃取數次,以及將形成的洗滌液過濾且於矽上蒸發。粗物料係經由使用0-10%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如白色固體之化合物F27(0.33g,56%)。
於氮氣下在乾燥的圓底燒瓶(50mL)內,將三乙
胺(0.358mL,2.57mmol)與甲苯磺醯氯(0.245g,1.29mmol),接著4-二甲胺吡啶(0.079g,0.64mmol),於冰浴溫度下添加至配於乾燥二氯甲烷(6.4mL)中經磁力攪拌的化合物F27(0.332g,1.29mmol)混合物。讓反應混合物於整個週末期間回溫至室溫。反應混合物係經由使用0-10%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如黃色固體之化合物F54(0.264g,71%)。
於氮氣下,將乾燥小瓶(25mL)中的碳酸銫
(0.155g,0.477mmol),添加至配於乾燥乙腈(2.39mL)之經磁力攪拌的化合物F54(0.132g,0.477mmol)及3,3,3-三氟丙-1-硫醇(0.0518mL,0.477mmol)之混合物內。反應混合物係於室溫下攪拌過夜。反應混合物係經由使用50-100%乙酸乙酯/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如白色固體之化合物19(0.0561g,30%)。
於氮氣下,將乾燥小瓶(25mL)中配於乾燥乙腈
(2.39mL)之經磁力攪拌的化合物F54(0.132g,0.477mmol)及甲硫醇鈉(0.0334g,0.477mmol)之混合物,於室溫下攪拌過夜。反應混合物係經由使用0-20%甲醇/乙酸乙酯作為沖提液之急速管柱層析法予以純化,以提供如白色固體之化合物40(0.0124g,9%)。
於室溫下將過氧硼酸鈉四水合物(0.062g,0.40
mmol),添加至配於乙酸(1.8mL)之化合物F20(0.050g,0.18mmol)溶液內。於55℃歷時1小時之後,使反應冷卻至室溫。反應係(小心地)以飽和的含水碳酸氫鈉及乙酸乙酯予以稀釋。將層予以分離,以及用乙酸乙酯萃取水層。組合的有機層係用鹽水清洗,於硫酸鈉上乾燥、過濾且於真空中濃縮。殘餘物係經由使用0-15%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如淡黃色固體之化合物51(0.0311g,53%)。
配於二甲亞碸(8.5mL)之化合物F27(0.258g,
1.00mmol)及戴斯-馬丁氧化劑(Dess-Martin periodinane)(0.509g,1.20mmol)混合物,係於室溫下攪拌12小時。混合物蒸發至乾燥,且用甲醇(100mL)來稀釋及過濾。移除溶劑以提供化合物CA1,其係一如醋酮之混合物之油)(0.200g,quant):ESIMS m/z 257([M+H]+)。
將甲氧基氯化銨(methoxyammonium chloride)
(0.0830g,1.00mmol)及乙酸(0.180g,3.00mmol),添加至配於乙醇(10mL)之化合物CA1(0.100g)混合物。該混合物於室溫下攪拌12小時。移除溶劑。粗產物係經由製備薄
層層析法予以純化,以提供如白色固體之化合物P26(0.0360g,25%)。
使用實施例45中揭示的程序,2-(4-側氧-2-(吡啶
-3-基)-2,4,6,7-四氫-5H-吡唑并[4,3-c]吡啶-5-基)乙醛O-苯甲基肟(化合物P27)係利用苯甲基氧基氯化銨來製備,以及單離為一種白色固體(0.036g,16%)。
於室溫下將含水氫化鈉(50mL,1mmol),添加
至配於甲醇(50mL)及四氫呋喃(25mL)之化合物F8(1.5g,5.0mmol)溶液內,接而攪拌歷時1小時。混合物係用鹽酸
(2N)來將pH調整至6。混合物蒸發至乾燥、用配於二氯甲烷之甲醇來清洗(甲醇/二氯甲烷1:8,200mL),以及過濾。將濾液濃縮,以提供如黃色固體之化合物CA2(1.35g,100%)。產物使用於下一個步驟不需進一步純化或是特徵化。
將N,O-二甲基羥胺鹽酸鹽(0.536g,5.50
mmol)、三乙胺(0.808g,8.00mmol)、1-羥苯并三唑(0.810g,6.00mmol),以及1-乙基-3-(3-二甲基胺丙基)碳二亞胺鹽酸鹽(1.34g,7.00mmol),添加至配於N,N-二甲基甲醯胺(50mL)之化合物CA2(1.36g,5.00mmol)溶液內。混合物係於室溫下攪拌過夜。反應混合物係用鹽酸(2N)(100mL)來稀釋,用乙酸乙酯(2 x 100mL)予以萃取。用氫氧化鈉將水相調整至pH 8,以及用二氯甲烷(3 x 100mL)萃取。
使組合的有機層於硫酸鈉上乾燥、過濾且濃縮,以提供如黃色固體之化合物CA3(1.42g,90%):mp 193-195℃;1H NMR(400MHz,CDCl3)δ 9.02(d,J=2.5Hz,1H),8.61
(dd,J=4.8,1.4Hz,1H),8.38(s,1H),8.03-8.02(m,1H),7.45(dd,J=8.3,4.8Hz,1H),4.50(s,2H),3.85-3.78(m,5H),3.24(s,3H),3.15(t,J=6.7Hz,2H);ESIMS m/z 316([M+H]+)。
於0℃下,將配於四氫呋喃(1M,8.00mL,8.00
mmol)之溴化甲鎂溶液,於氮氣下添加至配於無水四氫呋喃(66mL)之化合物CA3(1.33g,4.22mmol)溶液之內。讓反應回溫至室溫,以及攪拌歷時2小時。將飽和的含水氯化銨(120mL)添加至反應混合物,以及用乙酸乙酯(2 x 120mL)予以萃取。使組合的有機層於硫酸鈉上乾燥、過濾以及濃縮。藉由急速管柱層析法予以純化,提供如白色固體之化合物CA4(0.391g,28%):mp 206-207℃;1H NMR(400MHz,CDCl3)δ 9.03(d,J=2.3Hz,1H),8.61(d,J=3.8Hz,1H),8.40(s,1H),8.04(ddd,J=8.3,2.6,1.4Hz,1H),7.45(dd,J=8.3,4.7Hz,1H),4.39(s,2H),3.71(t,J=6.7Hz,2H),3.13(t,J=6.7Hz,2H),2.24(s,3H);ESIMS m/z 271
([M+H]+)。
使用實施例49中揭示的程序,5-(2-側氧-2-苯基
乙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P18)係利用溴化苯鎂來製備,以及單離為一種白色固體(0.430g,26%)。
使用實施例49中揭示的程序,5-(2-側氧
-2-(4-(三氟甲基)苯基)乙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P21)係利用(4-(三氟甲基)苯基)溴化鎂來製備,以及單離為一種白色固體(0.335g,27%)。
使用實施例49中揭示的程序,5-(2-側氧
-2-(3-(三氟甲基)苯基)乙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P20)係利用(3-(三氟甲基)苯基)溴化鎂來製備,以及單離為一種白色固體(0.270g,21%)。
使用實施例45中揭示的程序,5-(2-甲氧亞胺基)
丙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P30)係利用化合物CA4來製備,以及單離為一種白色固體(0.069g,77%)。
使用實施例45中揭示的程序,5-(2-苯甲基氧基)
亞胺基)丙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P31)係利用化合物CA4及苯甲基氧基氯化銨來製備,以及單離為一種白色固體(0.096g,58%)。
使用實施例45中揭示的程序,5-(2-甲氧亞胺
基)-2-苯基乙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P32)係利用化合物P18和甲基氧基氯化銨來製備,以及單離為一種白色固體(0.058g,53%)。
使用實施例45中揭示的程序,5-(2-苯甲基氧基)
亞胺基)-2-苯基乙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑
并[4,3-c]吡啶-4-酮(化合物P36)係利用化合物P18及苯甲基氧基氯化銨來製備,以及單離為一種白色固體(0.073g,55%)。
使用實施例45中揭示的程序,5-(2-甲氧亞胺
基)-2-(3-(三氟甲基)苯基)乙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P36)係利用化合物P20和甲基氧基氯化銨來製備,以及單離為一種白色固體(0.027g,25%)。
使用實施例45中揭示的程序,5-(2-苯甲基氧基)
亞胺基)-2-(3-(三氟甲基)苯基)乙基)-2-(吡啶-3-基)-2,5,6,7-
四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P38)係利用化合物P20及苯甲基氧基氯化銨來製備,以及單離為一種白色固體(0.040g,31%)。
使用實施例45中揭示的程序,5-(2-甲氧亞胺
基)-2-(4-(三氟甲基)苯基)乙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P38)係利用化合物P21和甲基氧基氯化銨來製備,以及單離為一種黃色固體(0.030g,28%)。
使用實施例45中揭示的程序,5-(2-苯甲基氧基)
亞胺基)-2-(4-(三氟甲基)苯基)乙基)-2-(吡啶-3-基)-2,5,6,7-四氫-4H-吡唑并[4,3-c]吡啶-4-酮(化合物P39)係利用化合物P21及苯甲基氧基氯化銨來製備,以及單離為一種白色固體(0.036g,28%)。
將至配於水(19.7mL)和乙醇(157mL)之哌啶-2,4-二酮(2.00g,17.7mmol)及2-肼吡啶(1.93g,17.7mmol)之溶液內。反應係於室溫下攪拌過夜。反應混合物係於減壓下濃縮。殘餘物係以乙醇/甲苯予以共沸乾燥,
以提供黃色粉末。添加二甲基甲醯胺(7.07mL)接著1,1-二甲氧基-N,N-二甲基六亞甲基四胺(7.05mL,53.0mmol),以及反應係於90℃下加熱60分鐘。使反應冷卻至室溫,以及於減壓下濃縮。殘餘物係溶解於甲醇內,於Celite®上濃縮,以及經由使用1-15%甲醇/二氯甲烷作為沖提液之急速管柱層析法予以純化,以提供如黃色固體之化合物CE1(0.870g,22%)。
化合物CE2係依據實施例10中揭示的程序,利用(氯甲基)(甲基)硫烷來製備,以及單離為一種灰白色固體(0.014g,6%)。
下列分子係依據實施例45中揭示的程序來製造:
5-(甲基磺醯基甲基)-2-(2-吡啶基)-6,7-二氫吡唑
并[4,3-c]吡啶-4-酮(化合物CE3)係利用(氯甲基)(甲基)硫烷((chloromethyl)(methyl)sulfane)來製備,以及單離為一種黃色固體(0.0527g,27%)。
化合物CE4係依據實施例10中揭示的程序,利用1-溴-3-(三氟甲氧基)苯來製備,以及單離為一種澄清的油(0.0224g,22%)。
下列分子係依據實施例47中揭示的程序來製造:
2-(2-吡啶基)-5-[6-(三氟甲基)-2-吡啶基]-6,7-二
氫吡唑并[4,3-c]吡啶-4-酮(化合物CE5)係利用2-溴-6-(三氟甲基)吡啶來製備,以及單離為一種黃色固體(0.0691g,78%)。
下列分子係依據實施例47中揭示的程序來製造:
2-(2-吡啶基)-5-[5-(三氟甲基)-2-吡啶基]-6,7-二
氫吡唑并[4,3-c]吡啶-4-酮(化合物CE6)係利用2-溴-5-(三氟甲基)吡啶來製備,以及單離為一種綠色固體(0.0117g,13%)。
下列分子係依據實施例47中揭示的程序來製造:
2-(2-吡啶基)-5-[4-(三氟甲基)-2-吡啶基]-6,7-二
氫吡唑并[4,3-c]吡啶-4-酮(化合物CE7)係利用2-溴-4-(三氟甲基)吡啶來製備,以及單離為一種黃色固體(0.025g,28%)。
雖然某些具體例中業已描述本發明,但是本發明能在本發明的精神與範疇內予以進一步修飾。此申請案因而意欲涵蓋使用本發明通則之任何變化、用途或適應。再者,此申請案意欲涵蓋落在本發明所屬技藝已知或習用的實施,且落在由所附申請專利範圍內之此等偏離。
Claims (14)
- 一種殺蟲組成物,其包含式I的化合物或其任一農業上可接受的鹽類:其中:(a)R 1 、R 2 及R 3 各自獨立地選自於下列所構成的群組:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基、C3-C6環烷基、芳基、經取代的芳基、C1-C4烷基苯基、苯基、經取代的苯基、雜環基,以及經取代的雜環基,(b)其中各個該R1、R2及R3,當被取代時,具有一個或更多個獨立地選自於下列所構成的群組之取代基:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基,及C3-C6環烷基;(c)R 4 、R 5 、R 6 、R 7 及R 8 各自獨立地選自於下列所構成的群組:H、F、Cl、Br、CN、OH、C1-C4烷基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基,及C3-C6環烷基;(d)R 9 係選自於下列所構成的群組:H、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、(C1-C4烷基)(C3-C6環烷基)、C1-C4烷基苯基、C1-C4鹵烷基苯基、芳基、經取代的芳基、苯基、吡啶基(pyridiyl)、嘧啶基、經取代的苯基、經取代的吡啶基、(C1-C4烷基)C(=O)(苯基)、(C1-C4烷基)(鹵烷基)(苯基)、(C1-C4烷基)(鹵烷基)(烷基)、(C1-C4烷基)C(=O)O(C1-C4烷基)、(C1-C4烷基)C(=NOR10)R11、C(=O)(C1-C4烷基)S(=O)m(C1-C4烷基)、(C1-C4烷基)S(=O)m(C1-C4烷基)、(C1-C4烷基)S(=O)m(C1-C4鹵烷基)、C(=O)R13,及(C1-C4烷基)C(=O)N(RxRy),其中R9,當被取代時,具有一個或更多個獨立地選自於下列所構成的群組之取代基:F、Cl、CN、OH、C1-C4鹵烷基、C1-C4鹵烷氧基,及C1-C4烷氧基、嘧啶基,或是其中R x 及R y 一起形成一個6員飽和環狀基團或是一個含有一個氮雜原子之6員飽和環狀基團,且其中該環狀基團當被取代時,具有一個或更多個獨立地選自於下列所構成的群組之取代基:C1-C4烷基、C3-C6環烷基,及苯基;(e)R 10 及R 11 各自獨立地選自於下列所構成的群組:H、Cl、C1-C4烷基、C1-C4鹵烷基、C1-C4烷基苯基、苯基,及經取代的苯基、芳基、經取代的芳基,其中R 10 及R 11 ,當被取代時,具有一個或更多個獨立地選自於H或C1-C4鹵烷基之取代基;(f)R 13 係選自於下列所構成的群組:H、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、(C1-C4烷基)(C3-C6環烷基)、C1-C4烷基苯基、C1-C4鹵烷基苯基、苯基、吡啶基(pyridiyl)、嘧啶基、經取代的苯基、經取代的吡啶基、芳基、經取代的芳基、(C1-C4烷基)C(=O)(苯基)、(C1-C4烷基)(鹵烷基)(苯基)、(C1-C4烷基)(鹵烷基)(烷基)、(C1-C4烷基)C(=O)O(C1-C4烷基)、(C1-C4烷基)C(=NOR10)R11、C(=O)(C1-C4烷基)S(=O)m(C1-C4烷基)、(C1-C4烷基)S(=O)m(C1-C4烷基),及(C1-C4烷基)S(=O)m(C1-C4鹵烷基);(g)X 1 為N或CR12,其中R 12 係選自於下列所構成的群組:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C2-C4烯基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基、C3-C6環烷基、C1-C4烷基苯基、芳基、經取代的芳基、苯基、經取代的苯基、雜芳基,及經取代的雜芳基,以及其中R 12 ,當被取代時,具有一個或更多個獨立地選自於下列所構成的群組之取代基:H、F、Cl、Br、I、CN、NO2、OH、C1-C4烷基、C1-C4鹵烷基、C1-C4烷氧基、C1-C4鹵烷氧基,及C3-C6環烷基;(h)Q為O(氧),或S(硫);(i)n為0、1,或2;以及(j)m為0、1,或2。
- 如請求項1之組成物,其中n為0以及Q為氧或硫。
- 如請求項1之組成物,其中R13為(C1-C4烷基)S(=O)m(C1-C4烷基),以及m為0、1,或2。
- 如請求項1之組成物,其中R9不是氫。
- 如請求項1-4中任一項之組成物,其中R9為(C1-C4烷基)S(=O)m(C1-C4烷基)或(C1-C4烷基)S(=O)m(C1-C4鹵烷基),以及其中m為0、1,或2。
- 如請求項1-4中任一項之組成物,其中R9為C(=O)R13、C1-C4鹵烷基、(C1-C4烷基)C(=O)(苯基),或是(C1-C4烷基)(鹵烷基)(烷基)。
- 如請求項1-4中任一項之組成物,其中R9為(C1-C4烷基)C(=NOR10)R11,以及R11係選自於下列所構成的群組:H、C1-C4烷基、C1-C4鹵烷基、苯基及經取代的苯基。
- 如請求項1之組成物,其中:R1、R2、R3、R4、R5、R6、R7及R8為H;R9係選自於下列所構成的群組:C1-C3烷基、(C1-C2烷基)(C3-C4環烷基)、C1烷基苯基、苯基、嘧啶基、經取代的苯基、經取代的吡啶基、(C1烷基)C(=O)O(C1-C2烷基)、(C1-C2烷基)S(=O)m(C1烷基)、(C1-C2烷基)S(=O)m(C1-C3鹵烷基),及(C1烷基)C(=O)N(RxRy);X1為CR12,其中R12為H;Q為O;以及m為0、1,或2。
- 如請求項1-4及8-10中任一項之組成物,其進一步包含:(a)一個或多個化合物,其具有殺蜱蟎、殺藻、殺鳥(avicidal)、殺菌、殺真菌、除草、殺昆蟲、殺軟體動物、殺線蟲、滅鼠或殺病毒特性;或是(b)一個或多個化合物,其為拒食劑、驅鳥劑、化學絕育劑、除草劑安全劑、誘蟲劑、驅蟲劑、驅哺乳動物劑、交配干擾劑、植物活化劑、植物生長調節劑,或協力劑;或是(c)(a)及(b)二者。
- 如請求項1-4及8-10中任一項之組成物,其進一步包含一個或多個選自於下列之化合物:(3-乙氧基丙基)溴化汞、1,2-二氯丙烷、1,3-二氯丙烯、1-甲基環丙烯、1-萘酚、2-(辛基硫基)乙醇、2,3,5-三碘苯甲酸、2,3,6-TBA、2,3,6-TBA-二甲基銨、2,3,6-TBA-鋰、2,3,6-TBA-鉀、2,3,6-TBA-鈉、2,4,5-T、2,4,5-T-2-丁氧基丙基酯、2,4,5-T-2-乙基己基酯、2,4,5-T-3-丁氧基丙基酯、2,4,5-TB、2,4,5-T-丁氧基丙酯(butometyl)、2,4,5-T-丁氧基乙基酯(2,4,5-T-butotyl)、2,4,5-T-丁基酯、2,4,5-T-異丁基酯、2,4,5-T-異辛基酯、2,4,5-T-異丙基酯、2,4,5-T-甲基酯、2,4,5-T-戊基酯、2,4,5-T-鈉、2,4,5-T-三乙基銨、2,4,5-T-三乙醇胺、2,4-D、2,4-D-2-丁氧基丙基酯、2,4-D-2-乙基己基酯、2,4-D-3-丁氧基丙基酯、2,4-D-銨、2,4-DB、2,4-DB-丁基酯、2,4-DB-二甲基銨、2,4-DB-異辛基酯、2,4-DB-鉀、2,4-DB-鈉、2,4-D-丁氧基乙基酯、2,4-D-丁基酯、2,4-D-二乙基銨、2,4-D-二甲基銨、2,4-D-二乙醇胺、2,4-D-十二基銨、2,4-DEB、2,4-DEP、2,4-D-乙基酯、2,4-D-庚基銨、2,4-D-異丁基酯、2,4-D-異辛基酯、2,4-D-異丙基酯、2,4-D-異丙基銨、2,4-D-鋰、2,4-D-異辛酯(meptyl)、2,4-D-甲基酯、2,4-D-辛基酯、2,4-D-戊基酯、2,4-D-鉀、2,4-D-丙基酯、2,4-D-鈉、2,4-D-四氫呋喃甲基酯(tefuryl)、2,4-D-十四基銨、2,4-D-三乙基銨、2,4-D-參(2-羥基丙基)銨、2,4-D-三乙醇胺、2iP、2-甲氧基乙基氯化汞、2-苯基酚、3,4-DA、3,4-DB、3,4-DP、4-胺基吡啶、4-CPA、4-CPA-鉀、4-CPA-鈉、4-CPB、4-CPP、4-羥基苯乙基醇、8-羥基喹啉硫酸鹽、8-苯基汞氧基喹啉、阿巴汀(abamectin)、脫落酸(abscisic acid)、ACC、毆殺松(acephate)、亞醌蟎(acequinocyl)、亞滅培(acetamiprid)、家蠅磷(acethion)、乙草胺(acetochlor)、乙酯磷(acetophos)、乙醯蟲腈(acetoprole)、阿拉酸式苯(acibenzolar)、阿拉酸式苯(acibenzolar)-S-甲基、亞喜芬(acifluorfen)、甲基亞喜芬、亞喜芬鈉鹽(acifluorfen-sodium)、苯草醚(aclonifen)、內醯吖庚胺(acrep)、阿納寧(acrinathrin)、丙烯醛(acrolein)、丙烯腈、阿西佩它克斯(acypetacs)、阿西佩它克斯-銅(acypetacs-copper)、阿西佩它克斯-鋅(acypetacs-zinc)、拉草(alachlor)、棉鈴威(alanycarb)、阿苯達唑(albendazole)、得滅克(aldicarb)、十二嗎啉(aldimorph)、涕滅碸威(aldoxycarb)、阿特靈(aldrin)、亞列寧(allethrin)、蒜素(allicin)、二丙烯草胺(allidochlor)、阿洛胺菌素(allosamidin)、亞汰草(alloxydim)、亞汰草鈉鹽、烯丙醇、除害威(allyxycarb)、亞羅列克(alorac)、α-賽滅寧(alpha-cypermethrin)、α-安殺番(alpha-endosulfan)、辛唑嘧菌胺(ametoctradin)、胺酮(ametridione)、草殺淨(ametryn)、胺草酮(amibuzin)、胺唑草酮(amicarbazone)、拌種靈(amicarthiazol)、賽硫磷(amidithion)、磺胺蟎酯(amidoflumet)、醯嘧磺隆(amidosulfuron)、滅害威(aminocarb)、環丙嘧啶酸(aminocyclopyrachlor)、甲基環丙嘧啶酸、環丙嘧啶酸鉀鹽、氯胺吡啶酸(aminopyralid)、氯胺吡啶酸鉀鹽、氯胺吡啶酸-參(2-羥基丙基)銨鹽、甲基胺草磷(amiprofos-methyl)、胺草磷(amiprophos)、安美速(amisulbrom)、阿米通(amiton)、草酸阿米通、三亞蟎(amitraz)、殺草強(amitrole)、胺磺酸銨鹽、α-萘乙酸銨(ammonium α-naphthaleneacetate)、代森銨(amobam)、1-胺基丙基磷酸(ampropylfos)、安納巴松(anabasine)、嘧啶醇(ancymidol)、敵菌靈(anilazine)、莎稗磷(anilofos)、安尼速隆(anisuron)、蒽醌(anthraquinone)、安妥(antu)、唑磷嗪(apholate)、殺蟎特(aramite)、三氧化二砷、福美砷(asomate)、阿司匹靈(aspirin)、磺草靈(asulam)、磺草靈鉀鹽、磺草靈鈉鹽、乙基殺撲磷(athidathion)、阿特拉通(atraton)、草脫淨(atrazine)、金色制黴素(aureofungin)、四烯雌酮(aviglycine)、四烯雌酮鹽酸鹽、氧環唑(azaconazole)、印苦楝子素(azadirachtin)、草芬定(azafenidin)、亞滅松(azamethiphos)、四唑嘧磺隆(azimsulfuron)、乙基谷速松(azinphos-ethyl)、谷速松(azinphos-methyl)、滅蘇民(aziprotryne)、塞侖(azithiram)、偶氮苯(azobenzene)、亞環錫(azocyclotin)、偶氮磷(azothoate)、亞托敏(azoxystrobin)、菊乙胺酯(bachmedesh)、燕麥靈(barban)、六氟矽酸鋇、多硫化鋇、椒菊酯(barthrin)、BCPC、氟丁醯草胺(beflubutamid)、本達樂(benalaxyl)、本達樂-M、草除靈(benazolin)、草除靈二甲基銨鹽、乙基草除靈、草除靈鉀鹽、醯苯草酮(bencarbazone)、異噻蟲唑(benclothiaz)、免敵克(bendiocarb)、氟草胺(benfluralin)、免扶克(benfuracarb)、呋草黃(benfuresate)、麥鏽靈(benodanil)、免賴得(benomyl)、解草酮(benoxacor)、苯磷(benoxafos)、醌肟腙(benquinox)、免速隆(bensulfuron)、甲基免速隆(bensulfuron-methyl)、地散磷(bensulide)、免速達(bensultap)、苯他隆(bentaluron)、本達隆(bentazone)、本達隆鈉鹽、苯噻菌胺(benthiavalicarb)、苯噻菌胺-異丙基、苯噻硫氰(benthiazole)、草噁嗪(bentranil)、苯甲醯胺氧乙酸(benzadox)、苯甲醯胺氧乙酸銨鹽、氯化烷基二甲基苄基銨、苯瑪松(benzamacril)、苯瑪松-異丁基(benzamacril-isobutyl)、抑菌啉(benzamorf)、雙苯嘧草酮(benzfendizone)、苄草胺(benzipram)、苯并雙環酮(benzobicyclon)、吡草酮(benzofenap)、氟草黃(benzofluor)、苯基異羥肟酸(benzohydroxamic acid)、西脫蟎(benzoximate)、新燕靈(benzoylprop)、乙基新燕靈、苯噻隆(benzthiazuron)、苯甲酸苄酯、苯甲基腺嘌呤(benzyladenine)、黃連素(berberine)、氯化黃連素(berberine chloride)、β-賽扶寧(beta-cyfluthrin)、β-賽滅寧(beta-cypermethrin)、比托沙(bethoxazin)、雙環哌喃酮(bicyclopyrone)、必芬蟎(bifenazate)、治草醚(bifenox)、畢芬寧(bifenthrin)、吡氟菌酯(bifujunzhi)、畢拉草(bilanafos)、畢拉草鈉鹽、百蟎克(binapacryl)、病氰硝(bingqingxiao)、百亞列寧(bioallethrin)、苄呋烯菊酯(bioethanomethrin)、生物氯菊酯(biopermethrin)、生物苄呋菊酯(bioresmethrin)、聯苯、吡殺茲(bisazir)、噻枯唑(bismerthiazol)、雙草醚(bispyribac)、雙草醚鈉鹽、雙三氟蟲脲(bistrifluron)、比多農(bitertanol)、硫雙二氯酚(bithionol)、聯苯吡菌胺(bixafen)、保米黴素(blasticidin-S)、硼砂、波爾多(Bordeaux)混合液、硼酸、白克列(boscalid)、芸苔素內酯(brassinolide)、芸苔素內酯-乙基、小蠹集合信息素(brevicomin)、溴鼠隆(brodifacoum)、溴滅菊酯(brofenvalerate)、溴氟菊酯(brofluthrinate)、克草(bromacil)、克草鋰鹽、克草鈉鹽、溴敵隆(bromadiolone)、溴鼠胺(bromethalin)、溴苄呋菊酯(bromethrin)、溴苯烯磷(bromfenvinfos)、溴乙醯胺(bromoacetamide)、除草溴(bromobonil)、溴丁醯草胺(bromobutide)、保滿丹(bromocyclen)、溴-滴滴涕(DDT)、溴酚肟(bromofenoxim)、溴磷松(bromophos)、乙基溴磷松、新殺蟎(bromopropylate)、溴菌腈(bromothalonil)、溴苯腈(bromoxynil)、丁酸溴苯腈(bromoxynil butyrate)、庚酸溴苯腈(bromoxynil heptanoate)、辛酸溴苯腈(bromoxynil octanoate)、溴苯腈-鉀、殺莠敏(brompyrazon)、溴克座(bromuconazole)、溴硝醇(bronopol)、增效特(bucarpolate)、必克蝨(bufencarb)、佈敏納弗(buminafos)、布瑞莫(bupirimate)、布芬淨(buprofezin)、勃根第(Burgundy)混合液、白消安(busulfan)、畜蟲威(butacarb)、丁基拉草(butachlor)、布芬草(butafenacil)、抑草磷(butamifos)、佈伏斯(butathiofos)、丁烯草胺(butenachlor)、苄烯菊酯(butethrin)、丁硫咪唑酮(buthidazole)、丁硫啶(buthiobate)、丁噻隆(buthiuron)、佈嘉信(butocarboxim)、布托酯(butonate)、避蚊酮(butopyronoxyl)、丁酮碸威(butoxycarboxim)、仲丁靈(butralin)、丁苯草酮(butroxydim)、炔草隆(buturon)、丁基胺、丁酸鹽、二甲胂酸(cacodylic acid)、硫線磷(cadusafos)、苯酮唑(cafenstrole)、砷酸鈣、氯酸鈣、氰胺化鈣(calcium cyanamide)、多硫化鈣、鈣殺畏(calvinphos)、卡本二氯(cambendichlor)、毒殺芬(camphechlor)、樟腦(camphor)、四氯丹(captafol)、蓋普丹(captan)、嗎菌威(carbamorph)、氯滅殺威(carbanolate)、胺甲(carbaryl)、除草隆(carbasulam)、貝芬替(carbendazim)、苯磺酸貝芬替(carbendazim benzenesulfonate)、亞硫酸貝芬替(carbendazim sulfite)、雙醯草胺(carbetamide)、加保扶(carbofuran)、二硫化碳、四氯化碳、加芬松(carbophenothion)、丁基加保扶(carbosulfan)、羧酸唑(carboxazole)、環二混劑(carboxide)、萎鏽靈(carboxin)、克繁草(carfentrazone)、乙基克繁草、加普胺(carpropamid)、培丹(cartap)、培丹鹽酸鹽、香芹酚(carvacrol)、香芹酮(carvone)、CDEA、滅胞素(cellocidin)、CEPC、西拉洛(ceralure)、切欣特混合液(Cheshunt mixture)、蟎離丹(chinomethionat)、殼聚糖(chitosan)、克氯綜(chlobenthiazone)、甲氧基護谷(chlomethoxyfen)、氯醛糖(chloralose)、克攔本(chloramben)、克攔本銨鹽、克攔本二乙醇胺鹽、甲基克攔本、克攔本甲基銨鹽、克攔本鈉鹽、氯胺磷(chloramine phosphorus)、氯黴素(chloramphenicol)、雙胺靈(chloraniformethan)、克氯尼(chloranil)、丁醯草胺(chloranocryl)、剋安勃(chlorantraniliprole)、炔禾靈(chlorazifop)、炔丙基炔禾靈(chlorazifop-propargyl)、氯阿淨(chlorazine)、氯殺蟎(chlorbenside)、滅幼脲(chlorbenzuron)、冰片丹(chlorbicyclen)、滅落寧(chlorbromuron)、氯草靈(chlorbufam)、可氯丹(chlordane)、氯癸酮(chlordecone)、氯苯甲脒(chlordimeform)、氯苯甲脒鹽酸鹽、氯烯炔菊酯(chlorempenthrin)、氯氧磷(chlorethoxyfos)、1-(3-氯-4-乙氧苯基)-3,3-二甲基脲(chloreturon)、伐草克(chlorfenac)、伐草克銨鹽、伐草克鈉鹽、克凡派(chlorfenapyr)、2-(2-氯苯基)-1H-苯并咪唑(chlorfenazole)、殺蟎醇(chlorfenethol)、燕麥酯(chlorfenprop)、殺蟎酯(chlorfenson)、敵蟎丹(chlorfensulphide)、氯芬松(chlorfenvinphos)、克福隆(chlorfluazuron)、氟咪殺(chlorflurazole)、氯芴酸(chlorfluren)、氯芴酸-甲基(chlorfluren-methyl)、整形醇(chlorflurenol)、甲基整形醇、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、乙基氯嘧磺隆、氯甲磷(chlormephos)、矮壯素陽離子(chlormequat)、矮壯素(chlormequat chloride)、氯乙靈(chlornidine)、全滅草(chlornitrofen)、克氯苯(chlorobenzilate)、氯二硝萘(chlorodinitronaphthalene)、氯仿、滅蟎脒(chloromebuform)、滅蟲脲(chloromethiuron)、二氯甲氧苯(chloroneb)、氯鼠酮(chlorophacinone)、氯鼠酮-鈉(chlorophacinone-sodium)、氯化苦(chloropicrin)、三氯丙酸(chloropon)、克氯蟎(chloropropylate)、四氯異苯腈(chlorothalonil)、氯麥隆(chlorotoluron)、枯草龍(chloroxuron)、氯二甲酚(chloroxynil)、矮形磷(chlorphonium)、氯化磷(chlorphonium chloride)、氯辛硫磷(chlorphoxim)、滅蟲吡啶(chlorprazophos)、氯普卡(chlorprocarb)、克普芬(chlorpropham)、陶斯松(chlorpyrifos)、甲基陶斯松(chlorpyrifos-methyl)、四氯喹啉(chlorquinox)、氯磺隆(chlorsulfuron)、大克草(chlorthal)、二甲基大克草、單甲基大克草、草克樂(chlorthiamid)、克硫松(chlorthiophos)、克氯得(chlozolinate)、氯化膽鹼、可芬諾(chromafenozide)、瓜菊酯(cinerin)I、瓜菊酯II、瓜菊酯類(cinerins)、乙基環醯草酯(cinidon-ethyl)、環庚草醚(cinmethylin)、西速隆(cinosulfuron)、苯氰丁醯胺(ciobutide)、落草胺(cisanilide)、順式苄呋菊酯(cismethrin)、剋草同(clethodim)、甘寶素(climbazole)、2-氯-3,5-二碘吡啶-4-基乙酸酯(cliodinate)、炔草酯(clodinafop)、炔丙基炔草酯(clodinafop-propargyl)、除線威(cloethocarb)、苯噠嗪鉀(clofencet)、苯噠嗪鉀-鉀(clofencet-potassium)、克芬蟎(clofentezine)、氯貝酸(clofibric acid)、2-[4-(4-氯苯氧基)苯氧基]丙酸(clofop)、異丁基2-[4-(4-氯苯氧基)苯氧基]丙酸(clofop-isobutyl)、可滅蹤(clomazone)、克普草(clomeprop)、果美生長素(cloprop)、氯丙殺草(cloproxydim)、畢克草(clopyralid)、甲基畢克草、畢克草乙醇胺鹽(clopyralid-olamine)、畢克草鉀鹽、畢克草-參(2-羥基丙基)銨鹽、解毒喹(cloquintocet)、解毒喹-甲基(cloquintocet-mexyl)、氯酯磺草胺(cloransulam)、甲基氯酯磺草胺、氯氰碘柳胺(closantel)、可尼丁(clothianidin)、克黴唑(clotrimazole)、座果酸(cloxyfonac)、座果酸-鈉(cloxyfonac-sodium)、CMA、十二碳二烯醇(codlelure)、噻唑硫磷(colophonate)、乙酸銅、乙醯亞砷酸銅、砷酸銅、碳酸銅、鹼式、氫氧化銅、萘酸銅、油酸銅、氯氧化銅、矽酸銅、硫酸銅、鉻酸銅鋅、氯殺鼠靈(coumachlor)、克滅鼠(coumafuryl)、蠅毒磷(coumaphos)、殺鼠迷(coumatetralyl)、畜蟲磷(coumithoate)、丁香菌酯(coumoxystrobin)、CPMC、CPMF、CPPC、必滅草(credazine)、甲酚(cresol)、甲基鼠滅定(crimidine)、克羅米通(crotamiton)、丁烯磷(crotoxyphos)、育畜磷(crufomate)、冰晶石(cryolite)、誘蠅酮(cue-lure)、銅合浦單劑(cufraneb)、草隆(cumyluron)、福美銅氯(cuprobam)、氧化亞銅、莪術醇(curcumenol)、氰胺、氰草淨(cyanatryn)、氰乃淨(cyanazine)、施力松(cyanofenphos)、氰乃松(cyanophos)、果蟲磷(cyanthoate)、氰蟲醯胺(cyantraniliprole)、賽座滅(cyazofamid)、賽百摧(cybutryne)、環菌胺(cyclafuramid)、環丙醯胺酸(cyclanilide)、環戊烯菊酯(cyclethrin)、環草敵(cycloate)、環己醯亞胺(cycloheximide)、環蟎酯(cycloprate)、乙氰菊酯(cycloprothrin)、環磺隆(cyclosulfamuron)、環殺草(cycloxydim)、環莠隆(cycluron)、唑蟎氰(cyenopyrafen)、賽芬胺(cyflufenamid)、賽芬蟎(cyflumetofen)、賽扶寧(cyfluthrin)、賽伏草(cyhalofop)、丁基賽伏草、賽洛寧(cyhalothrin)、錫蟎丹(cyhexatin)、蟎蜱胺(cymiazole)、蟎蜱胺鹽酸鹽(cymiazole hydrochloride)、克絕(cymoxanil)、解草胺腈(cyometrinil)、伏賜丁(cypendazole)、賽滅寧(cypermethrin)、牧草快(cyperquat)、牧草快氯鹽(cyperquat chloride)、賽芬寧(cyphenothrin)、環丙津(cyprazine)、三環噻草胺(cyprazole)、環克座(cyproconazole)、賽普洛(cyprodinil)、酯菌胺(cyprofuram)、環草胺(cypromid)、環丙磺醯胺(cyprosulfamide)、賽滅淨(cyromazine)、賽滅磷(cythioate)、汰草龍(daimuron)、得拉本(dalapon)、得拉本鈣鹽、得拉本鎂鹽、得拉本鈉鹽、丁醯肼(daminozide)、噠幼酮(dayoutong)、邁隆(dazomet)、邁隆鈉鹽、DBCP、d-樟腦(d-camphor)、DCIP、DCPTA、滴滴涕(DDT)、咪菌威(debacarb)、癸磷錫(decafentin)、去甲基克百威(decarbofuran)、去氫乙酸(dehydroacetic acid)、異丁草胺(delachlor)、第滅寧(deltamethrin)、甲基滅賜松(demephion)、甲基滅賜松-O、甲基滅賜松-S、內吸磷(demeton)、甲基內吸磷、內吸磷-O、甲基內吸磷-O、內吸磷-S、甲基內吸磷-S、碸吸磷(demeton-S-methylsulphon)、甜菜安(desmedipham)、敵草淨(desmetryn)、d-反式氯炔丙菊酯(d-fanshiluquebingjuzhi)、汰芬隆(diafenthiuron)、得拉松(dialifos)、二醛酯(di-allate)、除線特(diamidafos)、矽藻土、大利松(diazinon)、酞酸二丁酯、丁二酸二丁酯、汰克草(dicamba)、汰克草-二甘醇胺(dicamba-diglycolamine)、汰克草二甲基銨鹽、汰克草二乙醇胺鹽(dicamba-diolamine)、汰克草異丙基銨鹽、甲基汰克草、汰克草乙醇胺鹽、汰克草鉀鹽、汰克草鈉鹽、汰克草三乙醇胺鹽、異氯磷(dicapthon)、二氯苯腈(dichlobenil)、除線磷(dichlofenthion)、益發靈(dichlofluanid)、二氯萘醌(dichlone)、雙(三氯羥乙基)脲(dichloralurea)、滅幼脲(dichlorbenzuron)、二氯甲丹(dichlorflurenol)、二氯甲丹-甲基(dichlorflurenol-methyl)、苄胺靈(dichlormate)、二氯丙烯胺(dichlormid)、二氯酚(dichlorophen)、2,4-滴丙酸(dichlorprop)、2-乙基己基2,4-滴丙酸(dichlorprop-2-ethylhexyl)、2,4-滴丙酸丁氧基乙酯(dichlorprop-butotyl)、2,4-滴丙酸二甲基銨鹽、2,4-滴丙酸乙基銨鹽、異辛基2,4-滴丙酸、甲基2,4-滴丙酸、2,4-滴丙酸-P、2,4-滴丙酸-P-2-乙基己基(dichlorprop-P-2-ethylhexyl)、2,4-滴丙酸-P-二甲基銨鹽、2,4-滴丙酸鉀鹽、2,4-滴丙酸鈉鹽、二氯松(dichlorvos)、賜克滅(dichlozoline)、苄氯三唑醇(diclobutrazol)、雙氯氰菌胺(diclocymet)、禾草靈(diclofop)、甲基禾草靈、達滅淨(diclomezine)、達滅淨-鈉、大克爛(dicloran)、雙氯磺草胺(diclosulam)、大克蟎(dicofol)、雙香豆素(dicoumarol)、大跨希(dicresyl)、雙特松(dicrotophos)、環蟲腈(dicyclanil)、二環隆(dicyclonon)、地特靈(dieldrin)、得氯蟎(dienochlor)、二依馬(diethamquat)、二依馬二氯鹽(diethamquat dichloride)、乙醯甲草胺(diethatyl)、乙基乙醯甲草胺、乙黴威(diethofencarb)、迪艾索諾(dietholate)、焦碳酸二乙酯(diethyl pyrocarbonate)、二乙甲苯醯胺(diethyltoluamide)、鼠得克(difenacoum)、待克利(difenoconazole)、戊味禾草靈(difenopenten)、乙基戊味禾草靈、枯莠隆(difenoxuron)、野燕枯(difenzoquat)、野燕枯甲硫酸鹽(difenzoquat metilsulfate)、噻鼠靈(difethialone)、氟蟎(diflovidazin)、二福隆(diflubenzuron)、吡氟草胺(diflufenican)、氟吡草腙(diflufenzopyr)、氟吡草腙鈉鹽、二氟林(diflumetorim)、敵草克(dikegulac)、敵草克-鈉(dikegulac-sodium)、二羥丙茶鹼(dilor)、滴馬提夫(dimatif)、四氟甲醚菊酯(dimefluthrin)、甲氟磷(dimefox)、唑隆(dimefuron)、哌草丹(dimepiperate)、菌核淨(dimetachlone)、地麥威(dimetan)、混滅威(dimethacarb)、二甲草胺(dimethachlor)、愛落殺(dimethametryn)、汰草滅(dimethenamid)、汰草滅-P(dimethenamid-P)、噻節因(dimethipin)、二甲嘧酚(dimethirimol)、大滅松(dimethoate)、達滅芬(dimethomorph)、苄菊酯(dimethrin)、卡百酸二甲酯(dimethyl carbate)、酞酸二甲酯、二甲基亞硝胺(dimethylvinphos)、敵蠅威(dimetilan)、草滅散(dimexano)、草噠酮(dimidazon)、醚菌胺(dimoxystrobin)、消蟎酚(dinex)、消蟎酚-帝克列杉(dinex-diclexine)、啶菌噁唑(dingjunezuo)、達克利(diniconazole)、達克利-M(diniconazole-M)、撻乃安(dinitramine)、大脫蟎(dinobuton)、白粉克(dinocap)、白粉克-4、白粉克-6、敵蟎消(dinocton)、地樂特(dinofenate)、硝戊酯(dinopenton)、硝丙酚(dinoprop)、戊硝酚(dinosam)、達諾殺(dinoseb)、乙酸達諾殺、達諾殺銨鹽、達諾殺二乙醇胺鹽(dinoseb-diolamine)、達諾殺鈉鹽、達諾殺三乙醇胺鹽、硝辛酯殺蟎劑(dinosulfon)、達特南(dinotefuran)、特樂酚(dinoterb)、乙酸特樂酚、硝丁酯(dinoterbon)、苯蟲醚(diofenolan)、殺力松(dioxabenzofos)、二氧威(dioxacarb)、大克松(dioxathion)、得伐鼠(diphacinone)、得伐鼠鈉鹽(diphacinone-sodium)、大芬滅(diphenamid)、二苯碸、二苯胺、胺樂靈(dipropalin)、異丙凈(dipropetryn)、雙硫氧吡啶(dipyrithione)、大刈特(diquat)、大刈特二溴鹽、環氧十九烷(disparlure)、賽松(disul)、二硫龍(disulfiram)、二硫松(disulfoton)、賽松鈉鹽、普得松(ditalimfos)、腈硫醌(dithianon)、大賽伏(dithicrofos)、二硫醚、汰硫草(dithiopyr)、達有龍(diuron)、春芹烯(d-limonene)、DMPA、DNOC、DNOC-銨鹽、DNOC-鉀鹽、DNOC-鈉鹽、十二環啉(dodemorph)、十二環啉(dodemorph)乙酸鹽、十二環啉苯甲酸鹽、多地辛(dodicin)、多地辛鹽酸鹽(dodicin hydrochloride)、多地辛-鈉、多寧(dodine)、朵芬娜賓(dofenapyn)、多明尼卡路(dominicalure)、多滅蟲(doramectin)、肼菌酮(drazoxolon)、DSMA、毒氟磷(dufulin)、EBEP、EBP、蛻皮甾酮(ecdysterone)、護粒松(edifenphos)、甘草津(eglinazine)、乙基甘草津(eglinazine-ethyl)、因滅汀(emamectin)、因滅汀苯甲酸鹽、EMPC、益避寧(empenthrin)、安殺番(endosulfan)、草多索(endothal)、草多索二銨鹽、草多索二鉀鹽、草多索二鈉鹽、因毒磷(endothion)、安特靈(endrin)、烯肟菌酯(enestroburin)、EPN、丙醯芸苔素內酯(epocholeone)、保幼醚(epofenonane)、依普座(epoxiconazole)、乙醯胺基阿維菌素(eprinomectin)、三唑磺(epronaz)、EPTC、抑草蓬(erbon)、鈣化醇(ergocalciferol)、二氯醯草胺(erlujixiancaoan)、富右旋反式丙烯菊酯(esdépalléthrine)、益化利(esfenvalerate)、戊草丹(esprocarb)、乙烯矽(etacelasil)、乙環唑(etaconazole)、抑他風(etaphos)、益地安(etem)、噻唑菌胺(ethaboxam)、克草胺(ethachlor)、乙丁烯氟靈(ethalfluralin)、胺苯磺隆(ethametsulfuron)、甲基胺苯磺隆、殺草胺(ethaprochlor)、乙烯利(ethephon)、磺噻隆(ethidimuron)、愛芬克(ethiofencarb)、硫草敵(ethiolate)、愛殺松(ethion)、乙嗪草酮(ethiozin)、乙蟲腈(ethiprole)、依瑞莫(ethirimol)、益硫磷(ethoate-methyl)、益覆滅(ethofumesate)、乙基己二醇(ethohexadiol)、普伏松(ethoprophos)、氯氟草醚(ethoxyfen)、乙基氯氟草醚、乙氧基喹啉(ethoxyquin)、亞速隆(ethoxysulfuron)、吲唑酯(ethychlozate)、甲酸乙酯(ethyl formate)、α-萘乙酸乙酯(ethyl α-naphthaleneacetate)、乙基-DDD、乙烯、二溴化乙烯、二氯化乙烯、環氧乙烷、乙蒜素(ethylicin)、乙基汞2,3-二羥基丙基硫醇酯、乙基乙酸汞、乙基溴化汞、乙基氯化汞、乙基磷酸汞、硝草酚(etinofen)、益尼普滅(etnipromid)、乙氧苯草胺(etobenzanid)、依芬寧(etofenprox)、依殺蟎(etoxazole)、依得利(etridiazole)、益多松(etrimfos)、丁香酚(eugenol)、EXD、凡殺同(famoxadone)、胺磺磷(famphur)、咪唑菌酮(fenamidone)、敵磺鈉(fenaminosulf)、芬滅松(fenamiphos)、咪菌腈(fenapanil)、芬瑞莫(fenarimol)、雙氧威(fenasulam)、抗蟎唑(fenazaflor)、芬殺蟎(fenazaquin)、芬克座(fenbuconazole)、芬佈賜(fenbutatin oxide)、解草唑(fenchlorazole)、解草唑-乙基(fenchlorazole-ethyl)、樂乃松(fenchlorphos)、解草啶(fenclorim)、芬硫克(fenethacarb)、五氟苯菊酯(fenfluthrin)、甲呋醯胺(fenfuram)、環醯菌胺(fenhexamid)、種衣酯(fenitropan)、撲滅松(fenitrothion)、酚菌酮(fenjuntong)、丁基滅必蝨(fenobucarb)、2,4,5-涕丙酸(fenoprop)、2,4,5-涕丙酸-3-丁氧基丙基(fenoprop-3-butoxypropyl)、2,4,5-涕丙酸-丁氧基丙酯(fenoprop-butometyl)、2,4,5-涕丙酸丁氧基乙酯(fenoprop-butotyl)、丁基2,4,5-涕丙酸、異辛基2,4,5-涕丙酸、甲基2,4,5-涕丙酸、2,4,5-涕丙酸鉀鹽、芬硫克(fenothiocarb)、芬噁寧(fenoxacrim)、芬諾尼(fenoxanil)、芬殺草(fenoxaprop)、乙基芬殺草、芬殺草-P、乙基芬殺草-P(fenoxaprop-P-ethyl)、異噁苯碸(fenoxasulfone)、芬諾克(fenoxycarb)、拌種咯(fenpiclonil)、吡氯氰菊酯(fenpirithrin)、芬普寧(fenpropathrin)、苯鏽啶(fenpropidin)、芬普福(fenpropimorph)、胺苯吡菌酮(fenpyrazamine)、芬普蟎(fenpyroximate)、殺雄嗪(fenridazon)、殺雄嗪-鉀(fenridazon-potassium)、殺雄嗪-丙基(fenridazon-propyl)、芬蟎酯(fenson)、繁福松(fensulfothion)、2-(2,4,5-三氯苯氧基)乙醇(fenteracol)、噻唑禾草靈(fenthiaprop)、乙基噻唑禾草靈、芬殺松(fenthion)、乙基芬殺松、三苯錫(fentin)、三苯錫乙酸鹽(fentin acetate)、三苯錫氯、三苯羥錫、四唑醯草胺(fentrazamide)、芳氟胺(fentrifanil)、非草隆(fenuron)、非草隆TCA、芬化利(fenvalerate)、富爾邦(ferbam)、富米綜(ferimzone)、硫酸亞鐵、芬普尼(fipronil)、麥草氟酯(flamprop)、異丙基麥草氟酯、麥草氟酯-M、甲基麥草氟酯、異丙基麥草氟酯-M(flamprop-M-isopropyl)、甲基麥草氟酯-M、伏速隆(flazasulfuron)、伏滅鼠(flocoumafen)、弗美托奎(flometoquin)、氟尼胺(flonicamid)、雙氟磺草胺(florasulam)、嘧蟎酯(fluacrypyrim)、伏寄普(fluazifop)、丁基伏寄普、甲基伏寄普、伏寄普-P、丁基伏寄普-P(fluazifop-P-butyl)、扶吉胺(fluazinam)、異丙吡草酯(fluazolate)、氟啶蜱脲(fluazuron)、氟蟲醯胺(flubendiamide)、氟苯并胺噻唑(flubenzimine)、氟酮磺隆(flucarbazone)、氟酮磺隆鈉鹽、氟吡磺隆(flucetosulfuron)、貝殺寧(fluchloralin)、伏克隆(flucofuron)、氟蟎脲(flucycloxuron)、護賽寧(flucythrinate)、護汰寧(fludioxonil)、聯苯氟(fluenetil)、氟噻蟲碸(fluensulfone)、氟噻草胺(flufenacet)、嘧蟲胺(flufenerim)、弗芬肯(flufenican)、氟芬隆(flufenoxuron)、三氟醚菊酯(flufenprox)、氟噠草酯(flufenpyr)、乙基氟噠草酯、丁蟲腈(flufiprole)、氟氯苯菊酯(flumethrin)、氟醯菌胺(flumetover)、氟節胺(flumetralin)、唑嘧磺草胺(flumetsulam)、氟每淨(flumezin)、氟烯草酸(flumiclorac)、戊基氟烯草酸、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、氟啉(flumorph)、可奪草(fluometuron)、氟比來(fluopicolide)、氟吡菌醯胺(fluopyram)、氟殺蟎(fluorbenside)、增糖胺(fluoridamid)、氟乙醯胺(fluoroacetamide)、福泰芬(fluorodifen)、乙羧氟草醚(fluoroglycofen)、乙基乙羧氟草醚、氟醯亞胺、唑啶草(fluoromidine)、氟除草醚(fluoronitrofen)、殺克丹(fluothiuron)、三氟苯唑(fluotrimazole)、氟嘧菌酯(fluoxastrobin)、氟胺草唑(flupoxam)、氟異丙嘧草酯(flupropacil)、氟鼠啶(flupropadine)、氟丙酸(flupropanate)、氟丙酸鈉、弗比南載夫隆(flupyradifurone)、氟啶嘧磺隆(flupyrsulfuron)、甲基氟啶嘧磺隆(flupyrsulfuron-methyl)、甲基氟啶嘧磺隆鈉鹽(flupyrsulfuron-methyl-sodium)、氟喹唑(fluquinconazole)、解草安(flurazole)、抑草丁(flurenol)、抑草丁-丁基(flurenol-butyl)、抑草丁-甲基(flurenol-methyl)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟氯比(fluroxypyr)、氟氯比丁氧基丙酯(fluroxypyr-butometyl)、氟氯比異辛酯(fluroxypyr-meptyl)、呋嘧醇(flurprimidol)、硫氟磺醯胺(flursulamid)、呋草酮(flurtamone)、護矽得(flusilazole)、氟硫滅(flusulfamide)、氟噻草酯(fluthiacet)、甲基氟噻草酯、氟停安(flutianil)、福多寧(flutolanil)、護汰芬(flutriafol)、福化利(fluvalinate)、氟唑菌醯胺(fluxapyroxad)、肟草安(fluxofenim)、福爾培(folpet)、氟磺胺草醚(fomesafen)、氟磺胺草醚鈉鹽、大福松(fonofos)、甲醯胺磺隆(foramsulfuron)、氟吡脲(forchlorfenuron)、甲醛、覆滅蟎(formetanate)、覆滅蟎鹽酸鹽、福木松(formothion)、藻蟎威(formparanate)、藻蟎威鹽酸鹽、調節膦(fosamine)、調節膦銨鹽、福賽得(fosetyl)、福賽得鋁(fosetyl-aluminium)、丁苯硫磷(fosmethilan)、甲基氯吡磷(fospirate)、福賽絕(fosthiazate)、丁硫環磷(fosthietan)、弗羅塔林(frontalin)、麥穗靈(fuberidazole)、氟草淨(fucaojing)、氟草醚(fucaomi)、氟奈西草林(funaihecaoling)、呋苯硫脲(fuphenthiourea)、乙二醇縮糠醛(furalane)、呋霜靈(furalaxyl)、炔呋菊酯(furamethrin)、福拉比(furametpyr)、呋線威(furathiocarb)、二甲呋醯胺(furcarbanil)、呋菌唑(furconazole)、呋菌唑(furconazole)-順式、糠醛菊酯(furethrin)、糠醛(furfural)、呋喃解草唑(furilazole)、伴種胺(furmecyclox)、呋甲硫菌靈(furophanate)、呋氧草醚(furyloxyfen)、γ-賽洛寧(gamma-cyhalothrin)、γ-HCH、格蟎酯(genit)、赤黴酸(gibberellic acid)、赤黴素(gibberellins)、甘氟(gliftor)、草銨膦(glufosinate)、草銨膦銨鹽、草銨膦-P、草銨膦-P銨鹽、草銨膦-P鈉鹽、固毆寧(glyodin)、乙二肟(glyoxime)、嘉磷塞(glyphosate)、嘉磷塞二銨、嘉磷塞二甲基銨、嘉磷塞異丙基銨、嘉磷塞單銨鹽、嘉磷塞鉀、嘉磷塞倍半鈉(glyphosate-sesquisodium)、嘉磷塞三甲基硫鹽(glyphosate-trimesium)、草甘二膦(glyphosine)、誘蟲十六酯(gossyplure)、誘殺烯混劑(grandlure)、灰黃黴素(griseofulvin)、雙胍辛(guazatine)、雙胍辛乙酸鹽(guazatine acetates)、丙烯酸喹啉酯(halacrinate)、合芬寧(halfenprox)、合芬隆(halofenozide)、鹵殺芬(halosafen)、合速隆(halosulfuron)、甲基合速隆、氟啶草(haloxydine)、合氯氟(haloxyfop)、合氯氟乙氧基乙酯(haloxyfop-etotyl)、甲基合氯氟、合氯氟-P、合氯氟-P乙氧基乙酯、甲基合氯氟-P、合氯氟鈉鹽、HCH、六甲蜜胺(hemel)、海母帕(hempa)、HEOD、飛佈達(heptachlor)、飛達松(heptenophos)、增產肟(heptopargil)、速殺硫磷(heterophos)、六氯丙酮(hexachloroacetone)、六氯苯、六氯丁二烯、六氯酚(hexachlorophene)、菲克利(hexaconazole)、六伏隆(hexaflumuron)、六氟鹽(hexaflurate)、紅鈴誘烯(hexalure)、己醯胺(hexamide)、菲殺淨(hexazinone)、己硫松(hexylthiofos)、合賽多(hexythiazox)、HHDN、赫洛塞呋(holosulf)、磺硝肟(huancaiwo)、磺草靈(huangcaoling)、環菌唑(huanjunzuo)、愛美隆(hydramethylnon)、汞加芬(hydrargaphen)、熟石灰(hydrated lime)、氰化氫(hydrogen cyanide)、烯蟲乙酯(hydroprene)、殺紋寧(hymexazol)、水奎威(hyquincarb)、IAA、IBA、埃卡瑞丁(icaridin)、依滅列(imazalil)、依滅列(imazalil)硝酸鹽、依滅列(imazalil)硫酸鹽、咪草酸(imazamethabenz)、甲基咪草酸(imazamethabenz-methyl)、咪草啶酸(imazamox)、咪草啶酸銨鹽、甲咪唑烟酸(imazapic)、甲咪唑烟酸銨鹽、依滅草(imazapyr)、依滅草異丙基銨鹽、滅草喹(imazaquin)、滅草喹銨鹽、甲基滅草喹、滅草喹鈉鹽、咪唑乙煙酸(imazethapyr)、咪唑乙煙酸銨鹽、依速隆(imazosulfuron)、易胺座(imibenconazole)、新煙鹼類(imicyafos)、益達胺(imidacloprid)、氯噻啉(imidaclothiz)、克熱淨(iminoctadine)、克熱淨三乙酸鹽、克熱淨三苯磺酸鹽(iminoctadine trialbesilate)、依普寧(imiprothrin)、依納素(inabenfide)、茚草酮(indanofan)、三嗪茚草胺(indaziflam)、因得克(indoxacarb)、枯瘟淨(inezin)、碘普尼(iodobonil)、碘卡佈(iodocarb)、碘甲烷(iodomethane)、碘甲磺隆(iodosulfuron)、甲基碘甲磺隆、甲基碘甲磺隆鈉鹽、碘芬磺隆(iofensulfuron)、碘芬磺隆-鈉(iofensulfuron-sodium)、碘苯腈(ioxynil)、碘苯腈辛酸鹽(ioxynil octanoate)、碘苯腈鋰鹽、碘苯腈鈉鹽、抑草津(ipazine)、種菌唑(ipconazole)、鹵苯胺唑(ipfencarbazone)、丙基喜樂松(iprobenfos)、依普同(iprodione)、異丙菌威(iprovalicarb)、抑吡嘧丹(iprymidam)、小蟲二醇烯(ipsdienol)、小蟲醇烯(ipsenol)、IPSP、依殺米朵孚斯(isamidofos)、依殺松(isazofos)、碳氯靈(isobenzan)、草特靈(isocarbamid)、水胺硫磷(isocarbophos)、異草定(isocil)、異氯甲橋(isodrin)、亞芬松(isofenphos)、甲基亞芬松、異索威(isolan)、丁草酮(isomethiozin)、異草完隆(isonoruron)、異丙林特(isopolinate)、滅必蝨(isoprocarb)、異丙樂靈(isopropalin)、亞賜圃(isoprothiolane)、異丙隆(isoproturon)、萘吡菌胺(isopyrazam)、異皮莫(isopyrimol)、獲賜松(isothioate)、異噻菌胺(isotianil)、愛速隆(isouron)、異凡二酮(isovaledione)、異草胺(isoxaben)、異氯草酮(isoxachlortole)、雙苯噁唑酸(isoxadifen)、雙苯噁唑酸-乙基(isoxadifen-ethyl)、異唑草酮(isoxaflutole)、異草醚(isoxapyrifop)、加福松(isoxathion)、依維菌素(ivermectin)、淨種磷(izopamfos)、茉莉油(japonilure)、茉酮菊酯(japothrins)、茉酮菊酯(jasmolin)I、茉酮菊酯II、茉莉酸(jasmonic acid)、甲磺蒽腙(jiahuangchongzong)、甲基硝啉(jiajizengxiaolin)、甲香菊酯(jiaxiangjunzhi)、解草完(jiecaowan)、解草稀(jiecaoxi)、護粒松(jodfenphos)、青春激素I(juvenile hormone I)、青春激素II、青春激素III、噻嗯菊酯(kadethrin)、特胺靈(karbutilate)、卡列他南(karetazan)、卡列他南-鉀(karetazan-potassium)、嘉賜黴素(kasugamycin)、嘉賜黴素鹽酸鹽(kasugamycin hydrochloride)、柯均林(kejunlin)、氯戊環(kelevan)、酮螺氧(ketospiradox)、酮螺氧-鉀(ketospiradox-potassium)、細胞分裂素(kinetin)、烯蟲炔酯(kinoprene)、克收欣(kresoxim-methyl)、庫卡辛(kuicaoxi)、乳氟禾草靈(lactofen)、λ-賽洛寧(lambda-cyhalothrin)、拉提路(latilure)、砷酸鉛(lead arsenate)、環草定(lenacil)、里琵菌素(lepimectin)、福賜松(leptophos)、靈丹(lindane)、雷尼汀(lineatin)、理有龍(linuron)、力輪松(lirimfos)、利露(litlure)、誘池蛾酯(looplure)、祿芬隆(lufenuron)、氯啶菌酯(lvdingjunzhi)、氯醯草膦(lvxiancaolin)、噻唑磷(lythidathion)、MAA、馬拉松(malathion)、順丁烯二醯肼(maleic hydrazide)、特蟎腈(malonoben)、麥芽糊精(maltodextrin)、MAMA、代森錳銅(mancopper)、鋅錳乃浦(mancozeb)、曼普胺(mandipropamid)、錳乃浦(maneb)、苦參鹼(matrine)、疊氮磷(mazidox)、MCPA、MCPA-2-乙基己基酯(MCPA-2-ethylhexyl)、MCPA-丁氧基乙酯、MCPA-丁基酯、MCPA二甲基銨鹽、MCPA二乙醇胺鹽、MCPA-乙基酯、MCPA-異丁基酯、MCPA-異辛基酯、MCPA-異丙基酯、MCPA-甲基酯、MCPA乙醇胺鹽、MCPA鉀鹽、MCPA鈉鹽、MCPA-硫乙基酯(MCPA-thioethyl)、MCPA三乙醇胺鹽、MCPB、MCPB-乙基酯、MCPB-甲基酯、MCPB鈉鹽、巴斯丹(mebenil)、滅加松(mecarbam)、苯并威(mecarbinzid)、四甲磷(mecarphon)、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸-2-乙基己基酯(mecoprop-2-ethylhexyl)、2-甲-4-氯丙酸二甲基銨鹽、2-甲-4-氯丙酸二乙醇胺鹽、2-甲-4-氯丙酸-亞乙基酯(mecoprop-ethadyl)、2-甲-4-氯丙酸-異辛基酯、2-甲-4-氯丙酸-甲基酯、2-甲-4-氯丙酸-P、2-甲-4-氯丙酸-P-2-乙基己基酯、2-甲-4-氯丙酸-P二甲基銨鹽、2-甲-4-氯丙酸-P-異丁基酯、2-甲-4-氯丙酸鉀鹽、2-甲-4-氯丙酸-P鉀鹽、2-甲-4-氯丙酸鈉鹽、2-甲-4-氯丙酸三乙醇胺鹽、殺蟎脒(medimeform)、地樂施(medinoterb)、乙酸地樂施、誘殺酯(medlure)、滅芬草(mefenacet)、吡唑二酸(mefenpyr)、吡唑二酸-二乙基酯(mefenpyr-diethyl)、美福泰(mefluidide)、美福泰二乙醇胺鹽、美福泰鉀鹽、十四碳二烯酸(megatomoic acid)、美納松(menazon)、滅派林(mepanipyrim)、氯氟醚菊酯(meperfluthrin)、甲苯諾(mephenate)、美福松(mephosfolan)、甲哌啶(mepiquat)、甲哌啶氯化物(mepiquat chloride)、甲哌啶五硼酸鹽(mepiquat pentaborate)、滅普寧(mepronil)、敵蟎普(meptyldinocap)、氯化汞、氧化汞、氯化亞汞、脫葉亞磷(merphos)、滅莠津(mesoprazine)、磺胺磺隆(mesosulfuron)、甲基磺胺磺隆(mesosulfuron-methyl)、硝磺草酮(mesotrione)、甲硫酚(mesulfen)、倍硫磷亞碸(mesulfenfos)、美氟綜(metaflumizone)、滅達樂(metalaxyl)、右滅達樂(metalaxyl-M)、聚乙醛(metaldehyde)、斯美地(metam)、斯美地銨鹽、唑醯草胺(metamifop)、苯草酮(metamitron)、斯美地鉀鹽、斯美地鈉鹽、滅草胺(metazachlor)、雙醚氯吡嘧磺隆(metazosulfuron)、間氯敵菌酮(metazoxolon)、滅特座(metconazole)、甲基涕巴(metepa)、二甲噠草伏(metflurazon)、甲基苯噻隆(methabenzthiazuron)、滅克松(methacrifos)、甲基丙樂靈(methalpropalin)、達馬松(methamidophos)、滅速克(methasulfocarb)、滅草唑(methazole)、呋菌胺(methfuroxam)、滅大松(methidathion)、甲殺丹(methiobencarb)、滅賜克(methiocarb)、甲硫嘧磺隆(methiopyrisulfuron)、甲硫涕巴(methiotepa)、美西除靈(methiozolin)、滅草恆(methiuron)、殺蟲乙烯磷(methocrotophos)、醚草通(methometon)、納乃得(methomyl)、美賜平(methoprene)、格草净(methoprotryne)、喹啉羧酸-丁基酯(methoquin-butyl)、甲醚菊酯(methothrin)、甲氧滴滴涕(methoxychlor)、滅芬諾(methoxyfenozide)、去草酮(methoxyphenone)、甲基唑磷嗪(methyl apholate)、溴甲烷、甲基丁香粉(methyl eugenol)、碘甲烷(methyl iodide)、異硫氰酸甲酯(methyl isothiocyanate)、甲基乙酯磷(methylacetophos)、甲氯仿、甲基殺草隆(methyldymron)、二氯甲烷、甲基苯甲酸汞(methylmercury benzoate)、甲基汞二氰二胺(methylmercury dicyandiamide)、甲基五氯苯氧化汞(methylmercury pentachlorophenoxide)、亞甲癸醯胺(methylneodecanamide)、免得爛(metiram)、吡喃隆(metobenzuron)、撲奪草(metobromuron)、美特寧(metofluthrin)、莫多草(metolachlor)、治滅蝨(metolcarb)、苯氧菌胺(metominostrobin)、磺草唑胺(metosulam)、蟲酮(metoxadiazone)、甲氧隆(metoxuron)、滅芬農(metrafenone)、滅必淨(metribuzin)、噻菌胺(metsulfovax)、磺隆(metsulfuron)、甲基磺隆(metsulfuron-methyl)、美文松(mevinphos)、治克威(mexacarbate)、邁森(mieshuan)、密滅汀(milbemectin)、倍脈心(milbemycin oxime)、代森環(milneb)、丙胺氟磷(mipafox)、滅蟻樂(mirex)、MNAF、蘑菇醇(moguchun)、稻得壯(molinate)、殺蟲單(molosultap)、庚醯草胺(monalide)、莫尼速隆(monisouron)、一氯乙酸、亞素靈(monocrotophos)、綠谷龍(monolinuron)、單嘧磺隆(monosulfuron)、單嘧磺隆-酯(monosulfuron-ester)、滅草隆(monuron)、滅草隆TCA(monuron TCA)、伐草快(morfamquat)、伐草快二氯鹽、嗎啉胍(moroxydine)、嗎啉胍鹽酸鹽(moroxydine hydrochloride)、茂硫磷(morphothion)、墨茲(morzid)、莫西菌素(moxidectin)、MSMA、誘蟲烯(muscalure)、邁克尼(myclobutanil)、滅克寧(myclozolin)、N-(乙基汞)-對-甲苯磺醯胺苯、代森鈉(nabam)、萘肽磷(naftalofos)、乃力松(naled)、萘、萘乙醯胺、萘二甲酸酐(naphthalic anhydride)、萘氧乙酸、萘普草(naproanilide)、滅落脫(napropamide)、納得爛(naptalam)、納得爛鈉鹽、納他黴素(natamycin)、草不龍(neburon)、氯硝柳胺(niclosamide)、氯硝柳胺-醇胺(niclosamide-olamine)、煙嘧磺隆(nicosulfuron)、尼古丁、伏蟻靈(nifluridide)、吡氯草胺(nipyraclofen)、烯啶蟲胺(nitenpyram)、硝乙脲噻唑(nithiazine)、滅殺草(nitralin)、氯啶(nitrapyrin)、戊氰威(nitrilacarb)、護谷(nitrofen)、三氟甲草醚(nitrofluorfen)、硝苯乙烯(nitrostyrene)、酞菌酯(nitrothal-isopropyl)、鼠特靈(norbormide)、氟草敏(norflurazon)、降菸鹼(nornicotine)、草完隆(noruron)、諾伐隆(novaluron)、多氟脲(noviflumuron)、尼瑞莫(nuarimol)、OCH、八氯二丙基醚(octachlorodipropyl ether)、辛噻酮(octhilinone)、呋醯胺(ofurace)、歐滅松(omethoate)、坪草丹(orbencarb)、歐弗拉洛(orfralure)、鄰二氯苯、嘧苯胺磺隆(orthosulfamuron)、歐塔路(oryctalure)、肟醚菌胺(orysastrobin)、歐拉靈(oryzalin)、奧斯索(osthol)、歐斯措莫(ostramone)、解草腈(oxabetrinil)、丙炔草酮(oxadiargyl)、樂滅草(oxadiazon)、毆殺斯(oxadixyl)、草氨酸酯(oxamate)、歐殺滅(oxamyl)、草噠松(oxapyrazon)、草噠松(2-羥基乙基)二甲基銨鹽(oxapyrazon-dimolamine)、草噠松鈉鹽、環氧嘧磺隆(oxasulfuron)、草酮(oxaziclomefone)、快得寧(oxine-copper)、歐索林酸(oxolinic acid)、咪唑(oxpoconazole)、咪唑反丁烯二酸鹽、嘉保信(oxycarboxin)、滅多松(oxydemeton-methyl)、異亞碸磷(oxydeprofos)、碸拌磷(oxydisulfoton)、復祿芬(oxyfluorfen)、氧化苦參鹼(oxymatrine)、土黴素(oxytetracycline)、土黴素鹽酸鹽(oxytetracycline hydrochloride)、巴克素(paclobutrazol)、哌蟲啶(paichongding)、對-二氯苯、對氟隆(parafluron)、巴拉刈(paraquat)、巴拉刈二氯鹽、巴拉刈硫酸二甲酯(paraquat dimetilsulfate)、巴拉松(parathion)、甲基巴拉松、苯吡醇(parinol)、克草猛(pebulate)、披扶座(pefurazoate)、壬酸(pelargonic acid)、平克座(penconazole)、賓克隆(pencycuron)、施得圃(pendimethalin)、戊苯吡菌胺(penflufen)、氟幼脲(penfluron)、平速爛(penoxsulam)、五氯酚(pentachlorophenol)、甲氯醯草胺(pentanochlor)、噻菌胺(penthiopyrad)、百滅寧(pentmethrin)、環戊草酮(pentoxazone)、佈福松(perfluidone)、百滅寧(permethrin)、烯草胺(pethoxamid)、氰烯菌胺(phenamacril)、葉枯淨(phenazine oxide)、棉胺寧(phenisopham)、芬硫磷(phenkapton)、甜菜寧(phenmedipham)、甜菜寧-乙基酯(phenmedipham-ethyl)、醯草隆(phenobenzuron)、酚丁滅寧(phenothrin)、苯蟎醚(phenproxide)、賽達松(phenthoate)、苯基汞脲(phenylmercuriurea)、苯基乙酸汞(phenylmercury acetate)、苯基汞氯化物(phenylmercury chloride)、焦兒茶酚之苯基汞衍生物(phenylmercury derivative of pyrocatechol)、硝酸苯汞(phenylmercury nitrate)、苯基汞水楊酸鹽(phenylmercury salicylate)、福瑞松(phorate)、毒鼠磷(phosacetim)、裕必松(phosalone)、氯瘟磷(phosdiphen)、硫環磷(phosfolan)、硫環磷-甲基(phosfolan-methyl)、甘胺硫磷(phosglycin)、益滅松(phosmet)、對氯硫磷(phosnichlor)、福賜米松(phosphamidon)、膦、磷克(phosphocarb)、磷、三磷錫(phostin)、巴賽松(phoxim)、甲基巴賽松(phoxim-methyl)、熱必斯(phthalide)、畢克爛(picloram)、畢克爛-2-乙基己基酯(picloram-2-ethylhexyl)、畢克爛-異辛基酯、畢克爛-甲基酯、畢克爛乙醇胺鹽、畢克爛鉀鹽、畢克爛三乙基銨鹽、畢克爛-參(2-羥基丙基)銨鹽、氟吡醯草胺(picolinafen)、啶氧菌酯(picoxystrobin)、殺鼠酮(pindone)、殺鼠酮-鈉(pindone-sodium)、唑啉草酯(pinoxaden)、哌丙靈(piperalin)、胡椒基丁氧化物、胡椒基環己烯酮(piperonyl cyclonene)、哌草磷(piperophos)、哌壯素(piproctanyl)、哌壯素溴化物(piproctanyl bromide)、增效醛(piprotal)、必美松(pirimetaphos)、比加普(pirimicarb)、嘧啶氧磷(pirimioxyphos)、必滅松(pirimiphos-ethyl)、亞特松(pirimiphos-methyl)、三氯殺三氯酯(plifenate)、聚胺基甲酸酯(polycarbamate)、保粒黴素(polyoxins)、保粒黴素丁(polyoxorim)、保粒黴素丁-鋅、多噻烷(polythialan)、亞砷酸鉀(potassium arsenite)、疊氮化鉀(potassium azide)、氰酸鉀、赤黴酸鉀(potassium gibberellate)、環烷酸鉀(potassium naphthenate)、多硫化鉀(potassium polysulfide)、硫氰酸鉀(potassium thiocyanate)、α-萘乙酸鉀(potassium α-naphthaleneacetate)、4,4-滴滴涕(pp’-DDT)、普亞烈寧(prallethrin)、早熟素I(precocene I)、早熟素II、早熟素III、普拉草(pretilachlor)、嘧啶松(primidophos)、氟嘧磺隆(primisulfuron)、甲基氟嘧磺隆、撲殺熱(probenazole)、撲克拉(prochloraz)、撲克拉-錳(prochloraz-manganese)、丙氯醇(proclonol)、丙腈津(procyazine)、撲滅寧(procymidone)、氨氟樂靈(prodiamine)、佈飛松(profenofos)、氟唑草胺(profluazol)、環丙氟靈(profluralin)、丙氟菊酯(profluthrin)、氯苯噻草酮(profoxydim)、甘撲津(proglinazine)、乙基甘撲津(proglinazine-ethyl)、調環酸(prohexadione)、調環酸-鈣(prohexadione-calcium)、茉莉酮(prohydrojasmon)、蜱虱威(promacyl)、普滅克(promecarb)、撲滅通(prometon)、佈滅淨(prometryn)、捕滅鼠(promurit)、雷蒙得(propachlor)、普羅帕脒(propamidine)、普羅帕脒二鹽酸鹽(propamidine dihydrochloride)、普拔克(propamocarb)、普拔克鹽酸鹽(propamocarb hydrochloride)、除草靈(propanil)、加護松(propaphos)、普拔草(propaquizafop)、毆蟎多(propargite)、撲蟲菊(proparthrin)、普拔根(propazine)、撲達松(propetamphos)、苯胺靈(propham)、普克利(propiconazole)、甲基鋅乃浦(propineb)、普樂寶(propisochlor)、安丹(propoxur)、丙苯磺隆(propoxycarbazone)、丙苯磺隆鈉鹽、丙基增效劑(propyl isome)、咪唑嘧磺隆(propyrisulfuron)、戊炔草胺(propyzamide)、丙氧喹啉(proquinazid)、骨酯素(prosuler)、甲硫磺樂靈(prosulfalin)、苄草丹(prosulfocarb)、三氟丙磺隆(prosulfuron)、乙噻唑磷(prothidathion)、胺丙威(prothiocarb)、胺丙威(prothiocarb)鹽酸鹽、丙硫菌唑(prothioconazole)、普硫松(prothiofos)、飛克松(prothoate)、丙苯烴菊酯(protrifenbute)、撲滅生(proxan)、撲滅生鈉鹽、拔地草(prynachlor)、吡達農(pydanon)、派滅淨(pymetrozine)、賜加落(pyracarbolid)、白克松(pyraclofos)、雙唑草腈(pyraclonil)、百克敏(pyraclostrobin)、派芬草(pyraflufen)、乙基派芬草(pyraflufen-ethyl)、必伏清(pyrafluprole)、嘧啶威(pyramat)、唑胺菌酯(pyrametostrobin)、唑菌酯(pyraoxystrobin)、磺醯草吡唑(pyrasulfotole)、苄草唑(pyrazolynate)、白粉松(pyrazophos)、百速隆(pyrazosulfuron)、乙基百速隆(pyrazosulfuron-ethyl)、彼硫磷(pyrazothion)、匹唑芬(pyrazoxyfen)、吡菊酯(pyresmethrin)、除蟲菊精I(pyrethrin I)、除蟲菊精II、除蟲菊精類、草醚-異丙基酯(pyribambenz-isopropyl)、草醚-丙基酯(pyribambenz-propyl)、吡菌苯威(pyribencarb)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、三氯吡啶醇(pyriclor)、畢達本(pyridaben)、噠草福(pyridafol)、啶蟲丙醚(pyridalyl)、必芬松(pyridaphenthion)、必汰草(pyridate)、雙滴保(pyridinitril)、比芬諾(pyrifenox)、氟蟲吡喹(pyrifluquinazon)、環酯草醚(pyriftalid)、派美尼(pyrimethanil)、畢汰芬(pyrimidifen)、嘧草醚(pyriminobac)、甲基嘧草醚(pyriminobac-methyl)、嘧啶硫蕃(pyrimisulfan)、嘧硫磷(pyrimitate)、滅鼠優(pyrinuron)、甲氧苯啶菌(pyriofenone)、必清(pyriprole)、吡啶醇(pyripropanol)、百利普芬(pyriproxyfen)、嘧硫草醚(pyrithiobac)、嘧硫草醚鈉鹽、吡唑威(pyrolan)、百快隆(pyroquilon)、吡唑碸(pyroxasulfone)、吡唑磺草胺(pyroxsulam)、氯甲氧吡啶(pyroxychlor)、氯吡根呋醚(pyroxyfur)、苦木(quassia)、喹烯酮(quinacetol)、喹烯酮硫酸鹽、拜裕松(quinalphos)、甲基拜裕松(quinalphos-methyl)、醌菌腙(quinazamid)、快克草(quinclorac)、喹克座(quinconazole)、氯甲喹啉酸(quinmerac)、莫克草(quinoclamine)、克藻胺(quinonamid)、畜寧磷(quinothion)、快諾芬(quinoxyfen)、喹硫磷(quintiofos)、五氯硝苯(quintozene)、快伏草(quizalofop)、快伏草-乙基酯(quizalofop-ethyl)、快伏草-P、快伏草-P-乙基酯(quizalofop-P-ethyl)、快伏草-P-四氫呋喃甲基酯(quizalofop-P-tefuryl)、驅蚊酯(quwenzhi)、驅蠅啶(quyingding)、吡咪唑(rabenzazole)、碘醚柳胺(rafoxanide)、二乙基苯甲醯胺(rebemide)、列滅寧(resmethrin)、硫氰苯胺(rhodethanil)、鬧羊花毒素-III(rhodojaponin-III)、病毒唑(ribavirin)、碸嘧磺隆(rimsulfuron)、魚藤酮(rotenone)、蘭尼汀(ryania)、嘧啶肟草醚(saflufenacil)、噻菌茂(saijunmao)、噻森銅(saisentong)、柳醯胺苯、血根鹼(sanguinarine)、山道年(santonin)、八甲焦磷醯胺(schradan)、海蔥糖苷(scilliroside)、另丁津(sebuthylazine)、仲丁通(secbumeton)、環丙吡菌胺(sedaxane)、色拉菌素(selamectin)、單甲咪(semiamitraz)、單甲咪氯化物(semiamitraz chloride)、增效菊(sesamex)、芝麻啉(sesamolin)、西殺草(sethoxydim)、雙甲胺草磷(shuangjiaancaolin)、環草隆(siduron)、誘蟲環(siglure)、矽護芬(silafluofen)、雜氮矽三環(silatrane)、矽膠劑、矽噻菌胺(silthiofam)、草滅淨(simazine)、矽氟唑(simeconazole)、西瑪通(simeton)、西草淨(simetryn)、殺雄啉(sintofen)、SMA、左旋莫多草(S-metolachlor)、亞砷酸鈉、疊氮化鈉、氯酸鈉、氟化鈉、氟乙酸鈉、六氟矽酸鈉、環烷酸鈉(sodium naphthenate)、鄰苯基苯酚化鈉(sodium orthophenylphenoxide)、五氯酚鈉(sodium pentachlorophenoxide)、多硫化鈉(sodium polysulfide)、硫氰酸鈉、α-萘乙酸鈉(sodium α-naphthaleneacetate)、蘇硫磷(sophamide)、賜諾特(spinetoram)、賜諾殺(spinosad)、賜派芬(spirodiclofen)、螺甲蟎酯(spiromesifen)、螺蟲乙酯(spirotetramat)、螺環菌胺(spiroxamine)、鏈黴素(streptomycin)、鏈黴素倍半硫酸鹽(streptomycin sesquisulfate)、番木鼈鹼(strychnine)、食菌甲誘醇(sulcatol)、殺克隆(sulcofuron)、殺克隆-鈉、磺草酮(sulcotrione)、草克死(sulfallate)、氟磺唑草胺(sulfentrazone)、舒非侖(sulfiram)、氟蟲胺(sulfluramid)、嘧磺隆(sulfometuron)、甲基嘧磺隆(sulfometuron-methyl)、磺醯磺隆(sulfosulfuron)、治螟磷(sulfotep)、氟啶蟲胺腈(sulfoxaflor)、亞碸(sulfoxide)、硫肟磷(sulfoxime)、硫、硫酸、磺醯氟、蘇葡卡賓(sulglycapin)、硫丙磷(sulprofos)、戊苯碸(sultropen)、滅草靈(swep)、τ-福化利(tau-fluvalinate)、稗草烯(tavron)、噻蟎威(tazimcarb)、TCA、TCA銨鹽、TCA鈣鹽、TCA-亞乙基酯、TCA鎂鹽、TCA鈉鹽、TDE、得克利(tebuconazole)、得芬諾(tebufenozide)、得芬瑞(tebufenpyrad)、異丁乙氧喹啉(tebufloquin)、丁基嘧啶磷(tebupirimfos)、牧草胺(tebutam)、得匍隆(tebuthiuron)、克枯爛(tecloftalam)、四氯硝基苯(tecnazene)、福美雙聯(tecoram)、得福隆(teflubenzuron)、汰福寧(tefluthrin)、特呋三酮(tefuryltrione)、田寶三酮(tembotrione)、亞培松(temephos)、替哌(tepa)、TEPP、得殺草(tepraloxydim)、環戊烯丙菊酯(terallethrin)、特草定(terbacil)、特草靈(terbucarb)、特丁草胺(terbuchlor)、托福松(terbufos)、特丁通(terbumeton)、草淨津(terbuthylazine)、特丁淨(terbutryn)、四環唑(tetcyclacis)、四氯乙烷(tetrachloroethane)、樂本松(tetrachlorvinphos)、四克利(tetraconazole)、得脫蟎(tetradifon)、四氟隆(tetrafluron)、治滅寧(tetramethrin)、四氟醚菊酯(tetramethylfluthrin)、四胺、殺蟎黴素(tetranactin)、殺蟎硫醚(tetrasul)、硫酸鉈(thallium sulfate)、欣克草(thenylchlor)、θ-賽滅寧(theta-cypermethrin)、腐絕(thiabendazole)、賽果培(thiacloprid)、噻噠氟(thiadifluor)、賽速安(thiamethoxam)、蟲腈(thiapronil)、噻氟隆(thiazafluron)、噻草啶(thiazopyr)、賽伏(thicrofos)、噻菌腈(thicyofen)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、酮脲磺草吩酯(thiencarbazone)、甲基酮脲磺草吩酯(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆-甲基酯(thifensulfuron-methyl)、賽氟滅(thifluzamide)、殺丹(thiobencarb)、抗蟲威(thiocarboxime)、硫氯苯亞胺(thiochlorfenphim)、硫賜安(thiocyclam)、硫賜安鹽酸鹽(thiocyclam hydrochloride)、硫賜安草酸鹽(thiocyclam oxalate)、噻菌-銅(thiodiazole-copper)、硫敵克(thiodicarb)、硫伐隆(thiofanox)、硫氟肟(thiofluoximate)、不育硫磷(thiohempa)、硫柳汞(thiomersal)、硫滅松(thiometon)、治線磷(thionazin)、多保淨(thiophanate)、甲基多保淨(thiophanate-methyl)、克殺蟎(thioquinox)、胺基硫脲(thiosemicarbazide)、殺蟲雙(thiosultap)、殺蟲雙二銨(thiosultap-diammonium)、殺蟲雙二鈉、殺蟲雙單鈉、噻替派(thiotepa)、得恩地(thiram)、蘇力菌素(thuringiensin)、噻醯菌胺(tiadinil)、調劑胺(tiaojiean)、仲草丹(tiocarbazil)、6-氯-5-(甲基硫代基)嘧啶-2,4-二胺(tioclorim)、替係米(tioxymid)、威線肟(tirpate)、脫克松(tolclofos-methyl)、脫芬瑞(tolfenpyrad)、甲基益發靈(tolylfluanid)、甲苯基乙酸汞(tolymercury acetate)、吡草磺(topramezone)、三甲苯草酮(tralkoxydim)、溴氯氰菊酯(tralocythrin)、泰滅寧(tralomethrin)、曲洛比利(tralopyril)、拜富寧(transfluthrin)、反式百滅寧(transpermethrin)、曲他胺(tretamine)、三十烷醇(triacontanol)、三泰芬(triadimefon)、三泰隆(triadimenol)、氟酮磺草胺(triafamone)、燕麥畏(tri-allate)、三唑磷胺(triamiphos)、抑芽唑(triapenthenol)、三苯噻蟎吩(triarathene)、嘧菌醇(triarimol)、醚苯磺隆(triasulfuron)、唑蚜威(triazamate)、丁三唑(triazbutil)、三氟草胺(triaziflam)、三落松(triazophos)、唑菌(triazoxide)、苯磺隆(tribenuron)、苯磺隆-甲基酯(tribenuron-methyl)、脫葉磷(tribufos)、氧化三丁基錫、殺草畏(tricamba)、水楊菌胺(trichlamide)、三氯松(trichlorfon)、樂乃松(trichlormetaphos)-3、毒壤膦(trichloronat)、三氯比(triclopyr)、三氯比丁氧基乙酯(triclopyr-butotyl)、三氯比-乙基酯(triclopyr-ethyl)、三氯比三乙基銨鹽、三賽唑(tricyclazole)、三得芬(tridemorph)、三地芬(tridiphane)、草達津(trietazine)、蝸螺殺(trifenmorph)、三氯丙氧磷(trifenofos)、三氟敏(trifloxystrobin)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆鈉鹽、賽福座(triflumizole)、三福隆(triflumuron)、三福林(trifluralin)、氟胺磺隆(triflusulfuron)、甲基氟胺磺隆(triflusulfuron-methyl)、2-[4-[4-(三氟甲基)苯氧基]苯氧基]丙酸(trifop)、甲基2-[4-[4-(三氟甲基)苯氧基]苯氧基]丙酸(trifop-methyl)、三氟禾草肟(trifopsime)、賽福寧(triforine)、三羥基三、誘蠅羧酯(trimedlure)、混滅威(trimethacarb)、三甲隆(trimeturon)、抗倒酯(trinexapac)、抗倒酯-乙基(trinexapac-ethyl)、烯蟲硫酯(triprene)、三丙丹(tripropindan)、雷公藤甲素(triptolide)、草達克(tritac)、滅菌唑(triticonazole)、三氟甲磺隆(tritosulfuron)、特朗扣(trunc-call)、單克素(uniconazole)、單克素-P(uniconazole-P)、福美甲胂(urbacide)、烏瑞替派(uredepa)、戊酸酯(valerate)、維利黴素(validamycin)、伐利芬奈蕾特(valifenalate)、異殺鼠酮(valone)、繁米松(vamidothion)、泛佳(vangard)、凡力(vaniliprole)、萬隆(vernolate)、免克寧(vinclozolin)、華法林(warfarin)、華法林-鉀(warfarin-potassium)、華法林-鈉(warfarin-sodium)、硝蟲硫磷(xiaochongliulin)、辛菌胺(xinjunan)、烯肟菌胺(xiwojunan)、XMC、二甲苯草胺(xylachlor)、二甲苯酚(xylenols)、滅爾蝨(xylylcarb)、依希淨(yishijing)、氰菌胺(zarilamid)、玉米素(zeatin)、增效胺(zengxiaoan)、ζ-賽滅寧(zeta-cypermethrin)、萘酸鋅、磷化鋅(zinc phosphide)、噻唑鋅(zinc thiazole)、鋅乃浦(zineb)、福美鋅(ziram)、左拉伏(zolaprofos)、座賽胺(zoxamide)、唑嘧磺隆(zuomihuanglong)、α-氯醇(α-chlorohydrin)、α-蛻皮激素(α-ecdysone)、α-多紋素(α-multistriatin),及α-萘乙酸(α-naphthaleneacetic acid)。
- 如請求項1-4及8-10中任一項之組成物,其進一步包含以下化合物中之至少一者:(a)3-(4-氯-2,6-二甲基苯基)-4-羥基-8-氧-1-氮雜螺[4,5]癸-3-烯-2-酮(3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one);(b)3-(4'-氯-2,4-二甲基[1,1'-聯苯]-3-基)-4-羥基-8-氧-1-氮雜螺[4,5]癸-3-烯-2-酮;(c)4-[[(6-氯-3-吡啶基)甲基]甲基胺基]-2(5H)-呋喃酮;(d)4-[[(6-氯-3-吡啶基)甲基]環丙基胺基]-2(5H)-呋喃酮;(e)3-氯-N2-[(1S)-1-甲基-2-(甲基磺醯基)乙基]-N1-[2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]-1,2-苯二甲醯胺;(f)2-氰基-N-乙基-4-氟-3-甲氧基-苯磺醯胺;(g)2-氰基-N-乙基-3-甲氧基-苯磺醯胺;(h)2-氰基-3-二氟甲氧基-N-乙基-4-氟-苯磺醯胺;(i)2-氰基-3-氟甲氧基-N-乙基-苯磺醯胺;(j)2-氰基-6-氟-3-甲氧基-N,N-二甲基-苯磺醯胺;(k)2-氰基-N-乙基-6-氟-3-甲氧基-N-甲基-苯磺醯胺;(l)2-氰基-3-二氟甲氧基-N,N-二甲基苯磺醯胺;(m)3-(二氟甲基)-N-[2-(3,3-二甲基丁基)苯基]-1-甲基-1H-吡唑-4-甲醯胺;(n)N-乙基-2,2-二甲基丙醯胺-2-(2,6-二氯-α,α,α-三氟-對-甲苯基)腙;(o)N-乙基-2,2-二氯-1-甲基環丙烷-甲醯胺-2-(2,6-二氯-α,α,α-三氟-對甲苯基)腙菸鹼;(p)O-{(E-)-[2-(4-氯-苯基)-2-氰基-1-(2-三氟甲基苯基)-乙烯基]}S-甲基硫碳酸酯;(q)(E)-N1-[(2-氯-1,3-噻唑-5-基甲基)]-N2-氰基-N1-甲基乙脒;(r)1-(6-氯吡啶-3-基甲基)-7-甲基-8-硝基-1,2,3,5,6,7-六氫-咪唑并[1,2-a]吡啶-5-醇;(s)4-[4-氯苯基-(2-次丁基-亞肼基)甲基)]苯基甲磺酸酯;以及(t)N-乙基-2,2-二氯-1-甲基環丙烷甲醯胺-2-(2,6-二氯-α,α,α-三氟-對甲苯基)肼。
- 如請求項1-4及8-10中任一項之組成物,其進一步包含具有以下作用模式中之一者或多者的化合物:乙醯膽鹼酯酶抑制劑;鈉通道調節劑;甲殼素生物合成抑制劑;GABA及麩胺酸鹽閘控氯化物通道拮抗劑(GABA and glutamate-gated chloride channel antagonist);GABA及麩胺酸鹽閘控氯化物通道促效劑;乙醯膽鹼受體促效劑;乙醯膽鹼受體拮抗劑;MET I抑制劑;Mg刺激ATP酶抑制劑;菸鹼性乙醯膽鹼受體;中腸膜干擾劑;氧化磷酸化干擾劑,以及羅納丹受體(ryanodine receptor)(RyRs)。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461994660P | 2014-05-16 | 2014-05-16 | |
| US61/994,660 | 2014-05-16 |
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| Publication Number | Publication Date |
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| TW201623302A TW201623302A (zh) | 2016-07-01 |
| TWI662035B true TWI662035B (zh) | 2019-06-11 |
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| TW104115573A TWI662035B (zh) | 2014-05-16 | 2015-05-15 | 殺蟲組成物及相關方法 |
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| EP (1) | EP3145312B1 (zh) |
| JP (1) | JP6506308B2 (zh) |
| KR (1) | KR20170008753A (zh) |
| CN (1) | CN107072206B (zh) |
| AR (1) | AR100463A1 (zh) |
| AU (1) | AU2015259185B2 (zh) |
| BR (1) | BR112016026273B8 (zh) |
| CA (1) | CA2948365A1 (zh) |
| IL (1) | IL248781B (zh) |
| NZ (1) | NZ725781A (zh) |
| RU (1) | RU2016145145A (zh) |
| TW (1) | TWI662035B (zh) |
| UY (1) | UY36125A (zh) |
| WO (1) | WO2015175719A1 (zh) |
| ZA (1) | ZA201608046B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI897906B (zh) * | 2019-12-27 | 2025-09-21 | 日商石原產業股份有限公司 | 對有用植物的健康及/或成長帶來利益之方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI652014B (zh) | 2013-09-13 | 2019-03-01 | 美商艾佛艾姆希公司 | 雜環取代之雙環唑殺蟲劑 |
| JP6740239B2 (ja) | 2015-03-12 | 2020-08-12 | エフ エム シー コーポレーションFmc Corporation | 複素環置換二環式アゾール殺有害生物剤 |
| US10383335B2 (en) | 2015-04-09 | 2019-08-20 | Fmc Corporation | Bicyclic pyrazole pesticides |
| US11678660B2 (en) | 2016-12-30 | 2023-06-20 | Winfield Solutions, Llc | Drift reduction adjuvant compositions and methods of using same |
| US11612164B2 (en) | 2016-12-30 | 2023-03-28 | Winfield Solutions, Llc | Drift reduction adjuvant compositions and methods of using same |
| US10712232B2 (en) | 2017-09-11 | 2020-07-14 | Winfield Solutions, Llc | Flow diverting wind tunnel |
| US10533922B2 (en) | 2017-09-11 | 2020-01-14 | Winfield Solutions, Llc | Adjustable liquid trap for liquid waste drainage under differential pressure conditions |
| EP3732967A1 (en) * | 2017-12-26 | 2020-11-04 | Sumitomo Chemical Company Limited | Pest control composition and use of same |
| CN109019885A (zh) * | 2018-07-10 | 2018-12-18 | 上海洗霸科技股份有限公司 | 密闭式循环水系统无磷复合水处理剂及其制备方法与应用 |
| US10359337B1 (en) | 2018-11-21 | 2019-07-23 | Winfield Solutions, Llc | Test sections, wind tunnels including the same, and methods of using the same |
| US10499560B1 (en) | 2018-11-21 | 2019-12-10 | Winfield Solutions, Llc | Methods of using drift reduction adjuvant compositions |
| CA3069202A1 (en) | 2019-01-24 | 2020-07-24 | Winfield Solutions, Llc | Multifunctional agricultural adjuvant compositions |
| CN110073893A (zh) * | 2019-05-10 | 2019-08-02 | 绵阳市安州区保兴食用菌农业科技有限公司 | 一种羊肚菌的种植方法 |
| CN110551123A (zh) * | 2019-07-23 | 2019-12-10 | 常州合全药业有限公司 | 一种5-(叔丁氧羰基)-2-甲基-4,5,6,7-四氢-2h-吡唑并[4,3-c]吡啶-7-羧酸的制备方法 |
| CN114516869A (zh) * | 2020-11-20 | 2022-05-20 | 海利尔药业集团股份有限公司 | 一种螺环季酮酸类化合物或其作为农药可接受的盐、组合物及其用途 |
| EP4366733A4 (en) * | 2021-08-11 | 2025-06-25 | Landos Biopharma, Inc. | TETRAHYDROPYRAZOLOPYRIDINE ANALOGUES OF NLRX1 LIGANDS AND THEIR USES |
| CN113624882A (zh) * | 2021-08-14 | 2021-11-09 | 宁夏智联检测科学技术研究所(有限公司) | 水果蔬菜中咪鲜胺及其代谢产物残留量的检测方法 |
| CN118525002A (zh) | 2022-01-14 | 2024-08-20 | 恩科化学公司 | 原卟啉原氧化酶抑制剂 |
| US20260008780A1 (en) * | 2022-06-07 | 2026-01-08 | NodThera Limited | Substituted 3,4-dihydroisoquinolin-1(2h)-one derivatives and related uses |
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| US20110166143A1 (en) * | 2009-10-12 | 2011-07-07 | Bayer Cropscience Ag | Heterocyclic Compounds as Pesticides |
| WO2012061290A2 (en) * | 2010-11-03 | 2012-05-10 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| WO2012102387A1 (ja) * | 2011-01-27 | 2012-08-02 | 日産化学工業株式会社 | ピラゾール誘導体及び有害生物防除剤 |
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| US7135469B2 (en) * | 2003-03-18 | 2006-11-14 | Bristol Myers Squibb, Co. | Linear chain substituted monocyclic and bicyclic derivatives as factor Xa inhibitors |
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| EP1998620B1 (en) * | 2006-03-10 | 2011-01-12 | Neurogen Corporation | Piperazinyl oxoalkyl tetrahydroisoquinolines and related analogues |
| CN101686685A (zh) * | 2007-05-31 | 2010-03-31 | 先正达参股股份有限公司 | 保护植物繁殖材料、植物和/或植物器官的方法 |
| UA107791C2 (en) * | 2009-05-05 | 2015-02-25 | Dow Agrosciences Llc | Pesticidal compositions |
| BR112013010185A2 (pt) * | 2010-11-03 | 2016-07-05 | Dow Agrosciences Llc | composições pesticidas e processos relacionados às mesmas |
| US20120329649A1 (en) * | 2011-06-24 | 2012-12-27 | Hunter James E | Pesticidal compositions and processes related thereto |
| KR20140085527A (ko) * | 2011-10-26 | 2014-07-07 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 및 그와 관련된 방법 |
| JP2014015447A (ja) * | 2011-12-22 | 2014-01-30 | Nissan Chem Ind Ltd | ピラゾール誘導体および有害生物防除剤 |
| WO2013106254A1 (en) * | 2012-01-11 | 2013-07-18 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
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- 2015-05-13 BR BR112016026273A patent/BR112016026273B8/pt not_active IP Right Cessation
- 2015-05-13 CN CN201580027203.2A patent/CN107072206B/zh not_active Expired - Fee Related
- 2015-05-13 CA CA2948365A patent/CA2948365A1/en not_active Abandoned
- 2015-05-13 NZ NZ725781A patent/NZ725781A/en not_active IP Right Cessation
- 2015-05-13 US US14/711,559 patent/US9504251B2/en not_active Expired - Fee Related
- 2015-05-13 WO PCT/US2015/030662 patent/WO2015175719A1/en not_active Ceased
- 2015-05-13 RU RU2016145145A patent/RU2016145145A/ru not_active Application Discontinuation
- 2015-05-13 JP JP2016567251A patent/JP6506308B2/ja not_active Expired - Fee Related
- 2015-05-13 EP EP15791922.6A patent/EP3145312B1/en active Active
- 2015-05-13 KR KR1020167032268A patent/KR20170008753A/ko not_active Ceased
- 2015-05-15 UY UY0001036125A patent/UY36125A/es not_active Application Discontinuation
- 2015-05-15 AR ARP150101524A patent/AR100463A1/es active IP Right Grant
- 2015-05-15 TW TW104115573A patent/TWI662035B/zh not_active IP Right Cessation
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2016
- 2016-11-06 IL IL248781A patent/IL248781B/en active IP Right Grant
- 2016-11-21 ZA ZA2016/08046A patent/ZA201608046B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110166143A1 (en) * | 2009-10-12 | 2011-07-07 | Bayer Cropscience Ag | Heterocyclic Compounds as Pesticides |
| WO2012061290A2 (en) * | 2010-11-03 | 2012-05-10 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| WO2012102387A1 (ja) * | 2011-01-27 | 2012-08-02 | 日産化学工業株式会社 | ピラゾール誘導体及び有害生物防除剤 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI897906B (zh) * | 2019-12-27 | 2025-09-21 | 日商石原產業股份有限公司 | 對有用植物的健康及/或成長帶來利益之方法 |
Also Published As
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| RU2016145145A3 (zh) | 2018-11-08 |
| BR112016026273B8 (pt) | 2022-08-23 |
| BR112016026273A2 (pt) | 2017-08-15 |
| IL248781B (en) | 2019-07-31 |
| EP3145312B1 (en) | 2019-11-20 |
| NZ725781A (en) | 2018-03-23 |
| WO2015175719A1 (en) | 2015-11-19 |
| BR112016026273A8 (pt) | 2021-03-30 |
| KR20170008753A (ko) | 2017-01-24 |
| ZA201608046B (en) | 2018-05-30 |
| TW201623302A (zh) | 2016-07-01 |
| RU2016145145A (ru) | 2018-06-21 |
| BR112016026273B1 (pt) | 2021-07-13 |
| CN107072206B (zh) | 2020-02-21 |
| UY36125A (es) | 2016-01-08 |
| AU2015259185B2 (en) | 2018-01-18 |
| JP6506308B2 (ja) | 2019-04-24 |
| US20150327551A1 (en) | 2015-11-19 |
| EP3145312A1 (en) | 2017-03-29 |
| AU2015259185A1 (en) | 2016-11-17 |
| EP3145312A4 (en) | 2017-11-01 |
| JP2017515832A (ja) | 2017-06-15 |
| IL248781A0 (en) | 2017-01-31 |
| US9504251B2 (en) | 2016-11-29 |
| CN107072206A (zh) | 2017-08-18 |
| AR100463A1 (es) | 2016-10-05 |
| CA2948365A1 (en) | 2015-11-19 |
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