CN1328246C - 邻苯二酰胺衍生物或其盐,农业园艺用杀虫剂及其使用方法 - Google Patents
邻苯二酰胺衍生物或其盐,农业园艺用杀虫剂及其使用方法 Download PDFInfo
- Publication number
- CN1328246C CN1328246C CN99122802.2A CN99122802A CN1328246C CN 1328246 C CN1328246 C CN 1328246C CN 99122802 A CN99122802 A CN 99122802A CN 1328246 C CN1328246 C CN 1328246C
- Authority
- CN
- China
- Prior art keywords
- halo
- alkyl
- alkylthio
- alkoxyl group
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 title claims description 52
- 150000001408 amides Chemical class 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 25
- 150000003839 salts Chemical class 0.000 title claims description 25
- 239000000575 pesticide Substances 0.000 title claims description 21
- -1 (substituted) phenyl Chemical group 0.000 claims abstract description 119
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims description 287
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 82
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 58
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 42
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 150000003222 pyridines Chemical class 0.000 claims 4
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000005554 pyridyloxy group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 70
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 18
- 230000000749 insecticidal effect Effects 0.000 abstract description 9
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical class NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 abstract description 7
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000004419 alkynylene group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 description 119
- 238000006243 chemical reaction Methods 0.000 description 85
- 125000001309 chloro group Chemical group Cl* 0.000 description 77
- 238000012360 testing method Methods 0.000 description 75
- 125000001246 bromo group Chemical group Br* 0.000 description 49
- 239000000203 mixture Substances 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 229910052731 fluorine Inorganic materials 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 24
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 23
- 239000011737 fluorine Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000012442 inert solvent Substances 0.000 description 18
- 241000238631 Hexapoda Species 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 241000607479 Yersinia pestis Species 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- 101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 description 7
- 101100459319 Arabidopsis thaliana VIII-2 gene Proteins 0.000 description 7
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000244206 Nematoda Species 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 235000013311 vegetables Nutrition 0.000 description 6
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical class C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 241000985245 Spodoptera litura Species 0.000 description 5
- 239000012752 auxiliary agent Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 244000269722 Thea sinensis Species 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 241000243782 Tylenchida Species 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 241001556089 Nilaparvata lugens Species 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000003810 ethyl acetate extraction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000005826 halohydrocarbons Chemical class 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 238000005185 salting out Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- 241001672675 Adoxophyes Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000902805 Aulacophora Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 241001313742 Callosobruchus chinensis Species 0.000 description 2
- 241000426497 Chilo suppressalis Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000098289 Cnaphalocrocis medinalis Species 0.000 description 2
- 241000255749 Coccinellidae Species 0.000 description 2
- 241000157278 Dacus <genus> Species 0.000 description 2
- 241000586568 Diaspidiotus perniciosus Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 241000272317 Lipaphis erysimi Species 0.000 description 2
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 2
- 241001414662 Macrosteles fascifrons Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000409991 Mythimna separata Species 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 241001570894 Oulema oryzae Species 0.000 description 2
- 241001622642 Parnara bada Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241000437063 Phyllotreta striolata Species 0.000 description 2
- 241000254101 Popillia japonica Species 0.000 description 2
- 241001630079 Pseudaonidia duplex Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241001249129 Scirpophaga incertulas Species 0.000 description 2
- 241000254154 Sitophilus zeamais Species 0.000 description 2
- 241000176086 Sogatella furcifera Species 0.000 description 2
- 241000256247 Spodoptera exigua Species 0.000 description 2
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 2
- 241001267621 Tylenchulus semipenetrans Species 0.000 description 2
- 241001630065 Unaspis yanonensis Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000010413 gardening Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 235000019357 lignosulphonate Nutrition 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NWWJFMCCTZLKNT-UHFFFAOYSA-N 3,4-dihydro-2h-thiazine Chemical group C1CC=CSN1 NWWJFMCCTZLKNT-UHFFFAOYSA-N 0.000 description 1
- MGKIOAXLPYJSMU-UHFFFAOYSA-N 3-(trifluoromethoxy)benzoyl chloride Chemical compound FC(F)(F)OC1=CC=CC(C(Cl)=O)=C1 MGKIOAXLPYJSMU-UHFFFAOYSA-N 0.000 description 1
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical class C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000175828 Adoxophyes orana Species 0.000 description 1
- 241001155860 Aleurolobus Species 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241001198505 Anarsia lineatella Species 0.000 description 1
- 241000519878 Anomala rufocuprea Species 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241000294569 Aphelenchoides Species 0.000 description 1
- 241000680417 Aphelenchoides ritzemabosi Species 0.000 description 1
- 241001220428 Aphelenchus avenae Species 0.000 description 1
- 241001340598 Argyresthia conjugella Species 0.000 description 1
- 241001664281 Asphondylia Species 0.000 description 1
- 241001124183 Bactrocera <genus> Species 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241000254127 Bemisia tabaci Species 0.000 description 1
- 241000272639 Brachycaudus mimeuri Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- GKRYOTUQPZKDFB-UHFFFAOYSA-N C1=CC=CC=C1C(=O)OO.[Cl] Chemical compound C1=CC=CC=C1C(=O)OO.[Cl] GKRYOTUQPZKDFB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001347511 Carposina sasakii Species 0.000 description 1
- 235000009024 Ceanothus sanguineus Nutrition 0.000 description 1
- 241000630083 Ceroplastes ceriferus Species 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- 241000008892 Cnaphalocrocis patnalis Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241001635274 Cydia pomonella Species 0.000 description 1
- 241000084475 Delia antiqua Species 0.000 description 1
- 241001609607 Delia platura Species 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- 241000832201 Diaphania Species 0.000 description 1
- 241000526125 Diaphorina citri Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- QWDBCIAVABMJPP-UHFFFAOYSA-N Diisopropyl phthalate Chemical compound CC(C)OC(=O)C1=CC=CC=C1C(=O)OC(C)C QWDBCIAVABMJPP-UHFFFAOYSA-N 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000086608 Empoasca vitis Species 0.000 description 1
- 241001555556 Ephestia elutella Species 0.000 description 1
- 241001301805 Epilachna Species 0.000 description 1
- 241000462639 Epilachna varivestis Species 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241001442497 Globodera rostochiensis Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241001421695 Glyphodes pulverulentalis Species 0.000 description 1
- 241000751601 Glyphodes pyloalis Species 0.000 description 1
- 241001150406 Grapholita Species 0.000 description 1
- 241001441330 Grapholita molesta Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000255967 Helicoverpa zea Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 241001177117 Lasioderma serricorne Species 0.000 description 1
- 241000981121 Leguminivora glycinivorella Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000270322 Lepidosauria Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 240000003553 Leptospermum scoparium Species 0.000 description 1
- 241000396077 Listroderes Species 0.000 description 1
- 235000015459 Lycium barbarum Nutrition 0.000 description 1
- 241001043195 Lyctus brunneus Species 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241000243785 Meloidogyne javanica Species 0.000 description 1
- 241000254043 Melolonthinae Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- DAYXECLOGLTQIG-UHFFFAOYSA-N N#CO.[P] Chemical compound N#CO.[P] DAYXECLOGLTQIG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001190782 Phyllonorycter ringoniella Species 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 241000193943 Pratylenchus Species 0.000 description 1
- 241000193977 Pratylenchus musicola Species 0.000 description 1
- 241001446203 Pulvinaria aurantii Species 0.000 description 1
- 241000244173 Rhabditis Species 0.000 description 1
- IXOZPFMSAQUPFM-UHFFFAOYSA-N S1NCC1.N1CCC1 Chemical group S1NCC1.N1CCC1 IXOZPFMSAQUPFM-UHFFFAOYSA-N 0.000 description 1
- 241000545593 Scolytinae Species 0.000 description 1
- 241000563489 Sesamia inferens Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 241000074452 Spulerina simploniella Species 0.000 description 1
- 241000269319 Squalius cephalus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 241001271990 Tomicus piniperda Species 0.000 description 1
- 241000018135 Trialeurodes Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920013701 VORANOL™ Polymers 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 241000429635 Xestobium rufovillosum Species 0.000 description 1
- 241000064240 Yponomeuta padellus Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000218967 Zeugodacus <genus> Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- UUVBYOGFRMMMQL-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca].OP(O)(O)=O UUVBYOGFRMMMQL-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- MNQDKWZEUULFPX-UHFFFAOYSA-M dithiazanine iodide Chemical compound [I-].S1C2=CC=CC=C2[N+](CC)=C1C=CC=CC=C1N(CC)C2=CC=CC=C2S1 MNQDKWZEUULFPX-UHFFFAOYSA-M 0.000 description 1
- QLIHRMFUZWWSOI-UHFFFAOYSA-N dithiazinane Chemical group C1CNSSC1 QLIHRMFUZWWSOI-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- VMDHJFCXMLRQPZ-UHFFFAOYSA-N oxathiazinane Chemical group C1CNSOC1 VMDHJFCXMLRQPZ-UHFFFAOYSA-N 0.000 description 1
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical group O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- MQHNKCZKNAJROC-UHFFFAOYSA-N phthalic acid dipropyl ester Natural products CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- FJVZDOGVDJCCCR-UHFFFAOYSA-M potassium periodate Chemical compound [K+].[O-]I(=O)(=O)=O FJVZDOGVDJCCCR-UHFFFAOYSA-M 0.000 description 1
- HDMGAZBPFLDBCX-UHFFFAOYSA-M potassium;sulfooxy sulfate Chemical compound [K+].OS(=O)(=O)OOS([O-])(=O)=O HDMGAZBPFLDBCX-UHFFFAOYSA-M 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- AJZGFFKDLABHDD-UHFFFAOYSA-N thiazinane Chemical group C1CCSNC1 AJZGFFKDLABHDD-UHFFFAOYSA-N 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 210000003371 toe Anatomy 0.000 description 1
- 229950004288 tosilate Drugs 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/40—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/42—Y being a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
- C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
本发明提供了式(Ⅰ)的邻苯二酰胺衍生物,含有上述化合物作为活性成分并具有极好杀虫效果的农业园艺用杀虫剂:[其中A1为(取代的)C1-C8亚烷基、(取代的)C3-C8亚链烯基、(取代的)C3-C8亚炔基等,R1为H、(卤代)C3-C6环烷基、(取代的)苯基、(取代的)杂环、-A2-R4等,R2和R3为氢,C3-C6环烷基、-A2-R4等,A2为-C(=O)-、-C(=S)-或-C(=NR5)-,R4为H、烷基、(取代的)苯基、(取代的)杂环等,X和Y为卤素、氰基、硝基、(卤代)C1-C6烷基、(卤代)C1-C6烷氧基等,l为0-4,m为0-5,n为0-2]。
Description
本发明涉及一种邻苯二酰胺衍生物或其盐,含有上述化合物作为活性成分的农业园艺用杀虫剂,和使用上述农业园艺用试剂的方法。
JP-A-61-180753公开了一些本发明的邻苯二酰胺衍生物。可是,在上述专利申请说明书中,既没有公开也没有提示上述衍生物作为农业园艺用杀虫剂的有用性。而且,尽管类似化合物公开在JP-A-59-163353和J.C.S.Perkin I,1338-1350(1978)等中,但在上述出版物中没有述及或提示上述化合物作为农业园艺用杀虫剂的有用性。
为了开发新的农业园艺用试剂,本发明的发明人进行了深入的研究。结果发现了文献中未知的新化合物,即本发明通式(I)的邻苯二酰胺衍生物,可以作为不仅包含这些新化合物而且包含一些现有技术中已知的化合物的农业园艺用杀虫剂的新用途。基于上述发现,完成了本发明。
本发明涉及如下通式(I)所示的邻苯二酰胺衍生物或其盐,含有通式(I)所示的邻苯二酰胺衍生物或其盐和一些已知化合物作为活性成分的农业园艺用杀虫剂及其使用方法:
其中A1代表C1-C8亚烷基,具有至少一个相同或不同的取代基的取代C1-C8亚烷基,所述取代基选自卤原子、氰基、硝基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、羟基C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6烷硫基C1-C6烷基、C1-C6烷氧基羰基、苯基和具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,C3-C8亚链烯基,具有至少一个相同或不同的取代基的取代C3-C8亚链烯基,所述取代基选自卤原子、氰基、硝基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C1-C6烷硫基C1-C6烷基、C1-C6烷氧基羰基、苯基和具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,C3-C8亚炔基,或具有至少一个相同或不同的取代基的取代C3-C8亚炔基,所述取代基选自卤原子、氰基、硝基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C1-C6烷硫基C1-C6烷基、C1-C6烷氧基羰基,苯基和具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,
此外,在所述C1-C8亚烷基、取代C1-C8亚烷基、C3-C8亚链烯基、取代C3-C8亚链烯基、C3-C8亚炔基和取代C3-C8亚炔基中的任意饱和碳原子可被C2-C5亚烷基取代形成C3-C6环烷基环;在所述C1-C8亚烷基、取代C1-C8亚烷基、C3-C8亚链烯基和取代C3-C8亚链烯基中的任意两个碳原子可与亚烷基或亚链烯基连接形成C3-C6环烷基环或C3-C6环烯基环;
R1代表氢原子,巯基,C1-C6烷硫基,卤代C1-C6烷硫基,C3-C6环烷基,卤代C3-C6环烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯硫基,具有至少一个相同或不同的取代基的取代苯硫基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或-A2-R4[其中A2代表-C(=O)-,-C(=S)-,-C(=NR5)- (其中R5代表氢原子,C1-C6烷基,C1-C6烷氧基,单C1-C6烷基氨基,其中C1-C6烷基可以相同或不同的二C1-C6烷基氨基,C1-C6烷氧基羰基,苯基或具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基),
C1-C8亚烷基、卤代C1-C8亚烷基、C3-C6亚链烯基、卤代C3-C6亚链烯基、C3-C6亚炔基或卤代C3-C6亚炔基;和
(1)当A2代表-C(=O)-,-C(=S)-或-C(=NR5)-,其中R5如上所定义时,R4代表氢原子,C1-C6烷基,卤代C1-C6烷基,C3-C6环烷基,卤代C3-C6环烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或-Z1-R6,其中Z1代表-O-,-S-或-N(R7)-(其中R7代表氢原子、C1-C6烷基、C1-C6烷基羰基、卤代C1-C6烷基羰基或C1-C6烷氧基羰基),和R6代表氢原子,C1-C6烷基,卤代C1-C6烷基,C3-C6链烯基,卤代C3-C6链烯基,C3-C6炔基,卤代C3-C6炔基,C3-C6环烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯基C1-C4烷基,在其环上具有至少一个相同或不同的取代基的取代苯基C1-C4烷基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,或具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,和
(2)在A2代表C1-C8亚烷基、卤代C1-C8亚烷基、C3-C6亚链烯基、卤代C3-C6亚链烯基、C3-C6亚炔基或卤代C3-C6亚炔基时,R4代表氢原子,卤原子,氰基,硝基,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基羰基,单C1-C6烷基氨基羰基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或-Z2-R8,其中Z2代表-O-,-S-,-SO-,-SO2-,-N(R9)-(其中R9代表氢原子,C1-C6烷基,C1-C6烷基羰基,卤代C1-C6烷基羰基,C1-C6烷氧基羰基,苯基羰基,或具有至少一个相同或不同的取代基的取代苯基羰基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基),-C(=O)-或-C(=NOR10)-(其中R10代表氢原子,C1-C6烷基,卤代C1-C6烷基,C3-C6链烯基,卤代C3-C6链烯基,C3-C6炔基,卤代C3-C6炔基,C3-C6环烷基,苯基C1-C4烷基或在其环上具有至少一个相同或不同的取代基的取代苯基C1-C4烷基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基)和R8代表氢原子,C1-C6烷基,卤代C1-C6烷基,C3-C6链烯基,卤代C3-C6链烯基,C3-C6炔基,卤代C3-C6炔基,C3-C6环烷基,C1-C6烷基羰基,卤代C1-C6烷基羰基,C1-C6烷氧基羰基,单C1-C6烷基氨基羰基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯基C1-C4烷基,在其环上具有至少一个相同或不同的取代基的取代苯基C1-C4烷基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,或具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基],或
可选择地,R1可以与A1结合形成可以被1或2个相同或不同的氧原子,硫原子或氮原子间隔的5-至8-元环;
R2和R3可以是相同或不同的,代表氢原子、C3-C6环烷基或-A2-R4,其中A2和R4定义如上;或
可选择地,R2可以与A1或R1结合形成可以被1或2个相同或不同的氧原子,硫原子或氮原子间隔的5-至7-元环;
X可以是相同或不同的,代表卤原子,氰基,硝基,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基羰基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或-A3-R11[其中A3代表-O-、-S-、-SO-、-SO2-、-C(=O)-、-C(=NOR12)-(其中R12代表氢原子,C1-C6烷基,卤代C1-C6烷基,C3-C6链烯基,卤代C3-C6链烯基,C3-C6炔基,C3-C6环烷基,苯基C1-C4烷基或在其环上具有至少一个相同或不同的取代基的取代苯基C1-C4烷基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基),C1-C6亚烷基、卤代C1-C6亚烷基、C2-C6亚链烯基、卤代C2-C6亚链烯基、C2-C6亚炔基或卤代C3-C6亚炔基;和
(1)在A3代表-O-、-S-、-SO-或-SO2-时,R11代表卤代C3-C6环烷基,卤代C3-C6环烯基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或-A4-R13(其中A4代表C1-C6亚烷基、卤代C1-C6亚烷基、C3-C6亚链烯基、卤代C3-C6亚链烯基、C3-C6亚炔基或卤代C3-C6亚炔基,和R13代表氢原子,卤原子,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基羰基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或-A5-R14-(其中A5代表-O-、-S-、-SO-、-SO2-或-C(=O)-,和R14代表C1-C6烷基,卤代C1-C6烷基,C3-C6链烯基,卤代C3-C6链烯基,C3-C6炔基,卤代C3-C6炔基,C3-C6环烷基,卤代C3-C6环烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,或具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基)),和
(2)在A3代表-C(=O)-或-C(=NOR12)-,其中R12如上所定义时,R11代表氢原子,C1-C6烷基,卤代C1-C6烷基,C2-C6链烯基,卤代C2-C6链烯基,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基,C1-C6烷硫基,单C1-C6烷基氨基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯基氨基,在其环上具有至少一个相同或不同的取代基的取代苯基氨基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,或具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,和
(3)在A3代表C1-C6亚烷基、卤代C1-C6亚烷基、C2-C6亚链烯基、卤代C2-C6亚链烯基、C2-C6亚炔基或卤代C3-C6亚炔基时,R11代表氢原子,羟基,卤原子,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧羰基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或-A6-R15(其中A6代表-O-、-S-、-SO-或-SO2-,和R15代表C3-C6环烷基,卤代C3-C6环烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或-A7-R16(其中A7代表C1-C6亚烷基、卤代C1-C6亚烷基、C2-C6亚链烯基、卤代C2-C6亚链烯基、C2-C6亚炔基或卤代C3-C6亚炔基,和R16代表氢原子,卤原子,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯氧基,具有至少一个相同或不同的取代基的取代苯氧基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯硫基,具有至少一个相同或不同的取代基的取代苯硫基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,或具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基))];和1代表0至4的整数;和
可选择地,X可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基;和
Y可以是相同或不同的且代表卤原子,氰基,硝基,卤代C3-C6环烷基,其中C1-C6烷基可以是相同或不同的三C1-C6烷基甲硅烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或-A3-R11,其中A3和R11如上所定义;和m代表0至5的整数;和
Y可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,和具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基;和
n代表0至2的整数;
条件是当X,R2和R3同时代表氢原子,m代表整数2,2-位的Y代表氟原子和3-位的Y代表氯原子时,则A1不是亚丙基,R1不是甲基和n不是整数0。
在代表本发明邻苯二酰胺衍生物的通式(I)的定义中,术语“卤原子”的含义为氯原子、溴原子、碘原子或氟原子;术语“C1-C6烷基”的含义为具有1至6个碳原子的直链或支链烷基如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、正己基等;术语“卤代C1-C6烷基”的含义为可被至少一个相同或不同的卤原子取代的、具有1至6个碳原子的直链或支链烷基;术语“C1-C8亚烷基”的含义为具有1至8个碳原子的直链或支链亚烷基,如亚甲基、亚乙基、亚丙基、三亚甲基、二甲基亚甲基、四亚甲基、亚异丁基、二甲基亚乙基、八亚甲基等;术语“可被1至2个相同或不同的氧原子、硫原子或氮原子间隔的、通过R1与A1或R2与A1或R1形成的5-至8-或5-至7-元环”的含义为例如全氢化噻嗪环、噻唑烷环、硫杂氮杂环丁烷(thiazetidine)环、二氢噻嗪环、噻唑啉环、全氢化氧杂噻嗪环、二氢氧杂噻嗪环、二噻嗪、全氢化二噻嗪环等。
术语“杂环基”的含义为具有一个或多个相同或不同的选自氧原子、硫原子或氮原子的杂原子的5-至6-元杂环基,如吡啶基、吡啶-N-氧化物基、嘧啶基、呋喃基、四氢呋喃基、噻吩基、四氢噻吩基、四氢吡喃基、四氢噻喃基、唑基、异唑基、二唑基、噻唑基、异噻唑基、噻二唑基、咪唑基、三噻唑基、吡唑基等。术语“稠合环”例如为萘、四氢萘、茚、1,2-二氢化茚、喹啉、喹唑啉、吲哚、二氢吲哚、苯并呋喃、异苯并呋喃、苯并二烷、苯并间二氧杂环戊烯、苯并呋喃、二氢苯并呋喃、苯并噻吩、二氢苯并噻吩、苯并唑、苯并噻唑、苯并咪唑、吲唑等。
本发明通式(I)代表的邻苯二酰胺衍生物的盐例如为无机酸盐,如盐酸盐、硫酸盐、硝酸盐、磷酸盐等;有机酸盐如乙酸盐、富马酸盐、马来酸盐、草酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐等;和金属离子如钠离子、钾离子、钙离子等的盐。
一些本发明通式(I)代表的邻苯二酰胺衍生物在其结构式中含有不对称碳原子或不对称中心,且在一些情况下存在两个旋光异构体。本发明包括上述所有旋光异构体和由上述旋光异构体组成的任意比例的混合物。
本发明通式(I)的邻苯二酰胺衍生物或其盐的每个取代基的优选实例为A1为直链或支链C1-C8亚烷基;R1为C1-C6烷基或卤代C1-C6烷基;每个R2和R3为氢原子或C1-C6烷基;X为卤原子、硝基、C1-C6烷基、卤代C1-C6烷基或卤代C1-C6烷氧基;和Y为卤原子、C1-C6烷基、卤代C1-C6烷基或卤代C1-C6烷氧基。
通式(I)代表的本发明邻苯二酰胺衍生物例如可通过下述生产方法制备。
生产方法1
其中R1、R2、A1、X、Y、l、m和n如上所定义。
通式(V)的邻苯二甲酸酐衍生物与通式(IV)的苯胺在惰性溶剂存在下反应获得通式(III)的苯邻二甲酰亚胺衍生物。式(III)的苯邻二甲酰亚胺衍生物与通式(II)的胺反应后经分离或不经分离,可制备通式(I-1)的邻苯二酰胺衍生物。
(1)通
式(V)→通式(III)
作为在本反应中使用的惰性溶剂,可以使用任何溶剂,只要不明显抑制反应的进行,例如芳香烃如苯、甲苯、二甲苯等;卤代烃如二氯甲烷、氯仿、四氯化碳等;氯代芳烃如氯苯、二氯苯等;无环或环状醚如乙醚、二烷、四氢呋喃等;酯类如乙酸乙酯等;酰胺类如二甲基甲酰胺、二甲基乙酰胺等;酸类如乙酸等;二甲基亚砜;和1,3-二甲基-2-咪唑烷酮。上述惰性溶剂可单独或以其混合物使用。
由于该反应是等摩尔反应,使用等摩尔量的反应物是足够的,但可过量使用任一种反应物。如果需要,反应可在脱水条件下进行。
就反应温度而言,该反应可在室温至所用惰性溶剂的回流温度的温度范围内进行。尽管反应时间可根据反应规模、反应温度等变化,一般在几分钟至48小时的范围内适当选择。
反应完成后,通过常规方法从含有所需化合物的反应溶液中分离所需化合物,如果需要,通过重结晶、柱色谱等纯化,由此生产所需化合物。可将所需化合物不从反应溶液中分离而进行随后的反应。
通式(V)的邻苯二甲酸酐可通过在<有机化学杂志>(J.Org.Chem.),
52,129(1987),<美国化学会志>(J.Am.Chem.Soc.),
51,1865(1929),<美国化学会志>,
63,1542(1941)等中所述的方法制备。通式(IV)的苯胺可通过在<有机化学杂志>,
29,1(1964),Angew.Chem.Int.Ed.Engl.,
24,871(1985),<合成>(Synthesis),1984,667,<日本化学会公报>(Bulletin of the Chemical Society ofJapan),
1973,2351,DE-2606982,JP-A-1-90163等中所述的方法制备。
(2)通式(III)→通式(I-1)
在此反应中,可使用例如在上述反应(1)中所例举的惰性溶剂。
由于该反应是等摩尔反应,使用等摩尔量的反应物是足够的,但可过量使用通式(II)的胺。
就反应温度而言,该反应可在室温至所用惰性溶剂的回流温度的温度范围内进行。尽管反应时间可根据反应规模、反应温度等变化,一般在几分钟至48小时的范围内适当选择。
反应完成后,通过常规方法从含有所需化合物的反应溶液中分离所需化合物,如果需要,通过重结晶、柱色谱等纯化,由此生产所需化合物。
生产方法2
其中R1,R2,A1,X,Y,l,m和n如上所定义,X’是卤原子或硝基,条件是X不是氢原子或硝基。
在惰性溶剂存在下,通式(III-1)的苯邻二甲酰亚胺衍生物与相应于X的反应物反应,获得通式(III)的苯邻二甲酰亚胺衍生物。通式(III)的苯邻二甲酰亚胺衍生物与通式(II)的胺反应后经分离或不经分离,可生产通式(I-1)的邻苯二酰胺衍生物。
(1)通式(III-1)→通式(III)
根据<有机化学杂志>,
42,3415(1977),<四面体>(Tetrahedron),25,5921(1969),<合成>,
1984,667,<化学快报>(Chem.Lett.),1973,471,<有机化学杂志>,
39,3318(1974),<有机化学杂志>,39,3327(1974)等所述的方法进行该反应。
(2)通式(III)→通式(I-1)
本反应可根据生产方法1-(2)进行。
生产方法3
其中R1,R2,R3,A1,X,Y,l,m和n如上所定义。
在惰性溶剂存在下,通式(V)的邻苯二甲酸酐与通式(II)的胺反应,获得通式(III-4)的邻氨甲酰苯甲酸。经分离或不经分离,如下述处理通式(III-4)的邻氨甲酰苯甲酸。当通式(III-4)的邻氨甲酰苯甲酸的R2是氢原子时,在缩合剂存在下,通式(III-4)的邻氨甲酰苯甲酸缩合成通式(VI)的化合物,经分离或不经分离,在惰性溶剂存在下化合物(VI)与通式(IV’)的苯胺反应。当通式(III-4)的邻氨甲酰苯甲酸的R2不是氢原子时,在缩合剂存在下,通式(III-4)的邻氨甲酰苯甲酸与通式(VI)的苯胺缩合。由此可生产通式(I)的邻苯二酰胺衍生物。
可选择地,在惰性溶剂存在下,通式(V)的邻苯二甲酸酐衍生物与通式(IV’)的苯胺反应,获得通式(III-5)的邻氨甲酰苯甲酸。经分离或不经分离,如下述处理通式(m-5)的邻氨甲酰苯甲酸。当通式(III-5)的邻氨甲酰苯甲酸的R3是氢原子时,在缩合剂存在下,通式(III-5)的邻氨甲酰苯甲酸缩合成通式(VI-1)的化合物,经分离或不经分离,在惰性溶剂存在下化合物(VI-1)与通式(II)的胺反应。当通式(III-5)的邻氨甲酰苯甲酸的R3不是氢原子时,在缩合剂存在下,通式(III-5)的邻氨甲酰苯甲酸与通式(II)的胺缩合。由此可生产通式(I)的邻苯二酰胺衍生物。
(1)通式(V)或通式(VI-1)→分别获得通式(III-4)或通式(I)通过生产方法1-(2)的相同方法,由该反应生产所需化合物。
(2)通式(III-4)或通式(III-5)→分别获得通式(VI)或通式(VI-1)
所需化合物可根据<药物化学杂志>(J.Med.Chem.),
10,982(1967)所述方法由该反应制备。
(3)通式(VI)或通式(V)→分别获得通式(I)或通式(III-5)
通过生产方法1-(2)的相同方法,由该反应生产所需化合物。
(4)通式(III-4)或通式(III-5)→通式(I)
在缩合剂和惰性溶剂存在下,通式(III-4)或通式(III-5)的邻氨甲酰苯甲酸衍生物分别与通式(IV’)的苯胺或通式(II)的胺反应制备所需化合物。如果需要,该反应可在碱存在下进行。
在该反应中使用的惰性溶剂例如包括四氢呋喃、乙醚、二烷、氯仿和二氯甲烷。作为在该反应中使用的缩合剂,可以使用任何缩合剂,只要它是在一般酰胺合成中使用。缩合剂例如包括Mukaiyama试剂(如2-氯-N-甲基吡啶碘化物),1,3-二环己基碳化二亚胺(DCC),羰基二咪唑(CDI)和磷氰酸二乙酯(diethylphosphorocyanidate,DEPC)。对每摩尔通式(III-4)或通式(III-5)的邻氨甲酰苯甲酸衍生物,使用的缩合剂量可在1mol至过量摩尔数范围内适当选择。
作为可用于该反应中的碱,可以例举有机碱,如三乙胺、吡啶等,以及无机碱,如碳酸钾等。对每摩尔通式(III-4)或通式(III-5)的邻氨甲酰苯甲酸衍生物,碱的用量可在1mol至过量摩尔数范围内适当选择。
就反应温度而言,该该反应可在0℃至所用惰性溶剂的沸点温度的温度范围内进行。尽管反应时间可根据反应规模、反应温度等变化,一般在几分钟至48小时的范围内选择。
反应完成后,通过常规方法从含有所需化合物的反应溶液中分离所需化合物,如果需要,通过重结晶、柱色谱等纯化,由此生产所需化合物。
生产方法4
其中R1,R2,A1,X,Y,l,m和n如上所定义,和Hal是卤原子。
其中R1,Y和m如上所定义。
在惰性溶剂存在下通式(VII)的苯甲酰卤与通式(II)或通式(IV’)的胺衍生物反应获得通式(VIII-1)或(VIII-2)的苯甲酰胺。苯甲酰胺(VIII-1)或(VIII-2)用金属试剂如丁基锂等在邻位金属化,然后直接与通式(IX-1)或(IX-2)的异氰酸酯反应。可选择地,(VIII-1)或(VIII-2)的苯甲酰胺与二氧化碳反应获得通式(III-4’)或(III-5’)的邻氨甲酰苯甲酸,然后以生产方法3-(1)至(4)的相同方法处理。由此,可生产通式(I)的邻苯二酰胺衍生物。
(1)通式(VII)→通式(VIII-1)或通式(VIII-2)
根据<有机化学杂志>
32,3069(1967)等中描述的方法制备所需化合物。
(2)通式(VIII-1)或通式(VIII-2)→通式(I)
根据<有机化学杂志>
29,853(1964)中的描述,通过将通式(VIII-1)或通式(VIII-2)的苯甲酰胺转化为邻位-锂代(ortho-lithio)化合物,然后在-80℃至室温下与通式(IX-1)或(IX-2)的异氰酸酯反应,由此制备所需化合物。
(3)通式(VIII-1)或通式(VIII-2)→分别获得通式(III-4’)或通式(III-5’)
如(2)进行相同的邻位-锂代化合物转化,接着在-80℃至室温下引入二氧化碳而制备所需化合物。
反应完成后,通过常规方法从含有所需化合物的反应溶液中分离所需化合物,如果需要,通过重结晶、柱色谱等纯化,由此生产所需化合物。
(4)通式(III-4’)或通式(III-5’)→通式(I)
采用生产方法3-(1)至(4)的相同方法,生产所需化合物。
生产方法5
其中R1,R2,R3,A1,X,Y,l,m和n如上所定义,条件是n不能为整数0。
在惰性溶剂存在下通式(I-2)的邻苯二酰胺衍生物与氧化剂反应,由此生产通式(I-3)的邻苯二酰胺衍生物。
在此反应中使用的惰性溶剂例如卤代烃,如二氯甲烷、氯仿等,芳烃如甲苯、二甲苯等,酸类如乙酸等和醇类如甲醇、乙醇、丙醇等。
氧化剂例如有间-氯过苯甲酸,过乙酸,偏高碘酸钾、过硫酸氢钾(Oxon)、过氧化氢等。对每当量通式(I-2)的邻苯二甲酸二酰胺衍生物,氧化剂的量一般在0.5至3当量的范围内适当选择。
就反应温度而言,该反应可在-50℃至所用惰性溶剂的沸点温度的温度范围内进行。尽管反应时间可根据反应规模、反应温度等变化,一般在几分钟至24小时的范围内。
反应完成后,通过常规方法从含有所需化合物的反应溶液中分离所需化合物,如果需要,通过重结晶、柱色谱等纯化,由此生产所需化合物。
下面在表1、2和3中例举了典型的通式(I)邻苯二酰胺衍生物。本发明决不受这些实施例的限制。
表1 (R2=R3=H)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
12345678910111213141516171819202122 | CH(CH3)CH2SCH3CH(CH3)CH2S-i-C3H7CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2S-i-C3H7CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SPhCH(CH3)CH2SPhCH(CH3)CH2SPhCH(CH3)CH2SPhCH(CH3)CH2SC2H5CH(CH3)CH2SC2H5 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-F3-F3-F3-FHHH3-I3-I3-I3-I3-I3-I | 2-CH3-4-C2F52-CH3-4-C2F52-CH3-4-OCF32-CH3-4-OCHF22-CH3-4-OCF32-CH3-4-i-C3F72-Cl-4-C2F54-OCF32-CH3-4-Cl2-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-OCHF22-CH3-4-C2F52-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-i-C3F72-C2H5-4-C2F52-CH3-4-C2F52-CH3-4-i-C3F7 | 179-180糊状物147107126197-199143171-178179146-154140122-130149-154139-146140-144139-145糊状物糊状物糊状物糊状物糊状物107 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
23242526272829303132333435363738394041424344 | CH(CH3)CH2SC2H5CH(CH3)CH2SC2H5CH(CH3)CH2SC2H5CH(CH3)CH2SC2H5CH(CH3)CH2SC2H5CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2S-i-C4H9CH(CH3)CH2S-i-C4H9CH(CH3)CH2S-i-C4H9CH(CH2SCH3)2CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3 | 3-I3-I3-F3-F3-F3-I3-I3-I3-I3-I3-I3-I3-I3-I3,4-Cl25,6-Cl23,4-Cl25,6-Cl23,4-Cl25,6-Cl24-Cl3,4-F2 | 2-CH3-4-OCF32-CH3-4-Cl2-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-C2F52-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-SCF32-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-C2F52-CH3-4-OCF32-CH3-4-OCF32-CH3-4-C2F52-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF3 | 143161-166142糊状物142-1479410082134194-195164-172159-160155-159145197-199213-214221-222199-200215-216220-221178-179175-176 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
454647484950515253545556575859606162636465 | CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3(CH2)2SCH3(CH2)2SCH3(CH2)2SCH3(CH2)2SCH3(CH2)3SCH3(CH2)3SCH3(CH2)3SCH3(CH2)2S-i-C3H7(CH2)2S-i-C3H7(CH2)2S-i-C3H7CH(CH3)CH2S-2-PyiCH(CH3)CH2S-2-PyiCH(CH3)CH2S-n-C4H9CH(CH3)CH2S-n-C4H9CH(CH3)CH2SCH3 | 4,5-F23-I3-I3-I3-I3-I6-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH3-4-OCF32-CH3-4-OC-(C2F5)=C(CF3)22-Cl-4-OCF2-CHFO-52-Cl-4-OCHF-CF2O-52-OCH3-4-C2F52-C2H5-4-C2F52-CH3-4-OCF32-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-C2F52-Cl-4-i-C3F7 | 118-120196-197198192170125130-133145-150无定形无定形144-147165-168156-159189-192153-155158-160无定形140-142137-139无定形190 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
66676869707172737475767778798081828384858687 | CH(CH3)CH2SCH3CH(CH2SCH3)2CH(CH2SCH3)2CH(CH2SCH3)2CH(CH2SCH3)2(CH2)2SC2H5(CH2)2SC2H5(CH2)2SC2H5CH(CH3)CH2S-2-PyiCH(CH3)CH2SO-2-PyiCH(CH3)CH2SO2-2-PyiCH(CH3)CH2S-n-C6H13CH(CH3)CH2S-n-C6H13CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2S-c-C6H11CH(CH3)CH2S-t-C4H9CH(CH3)CH2S-t-C4H9CH(CH3)CH2S-c-C6H11CH(CH3)CH2S-c-C8H11CH(CH3)CH2SOCH3 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-Br3-Br3-Br3-I3-I3-I3-I3-I3-Br | 2-C2H5-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF2CHF22-CH3-4-OCF32-CH3-4-OCHF22-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-C2F52-CH3-4-OCF32-CH3-4-OCF32-CH3-4-C2F52-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF3 | 205181169-176131-139142157-161152-155159-162203110-11199-100无定形152-153201-202195194-195166-167188-189183-184102-10395-96212-213 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
888990919293949596979899100101102103104105106107108109 | CH(CH3)CH2SO2CH3CH(Ph)CH2SCH3CH(Ph)CH2SCH3CH(Ph)CH2SCH3CH(CH3)(CH2)3SCH3CH(CH3)(CH2)3SCH3CH(CH3)(CH2)3SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SO2CH3CH(CH3)CH2SO2CH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3 | 3-Br3-I3-I3-I3-I3-I3-I3-Br3-Br3-Br3-Cl3-Cl3-Cl3-Cl3-I3-I3-NO23-NO23-NO24-I4-I4-I | 2-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-C2F52-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-i-C3F72-Cl-4-OCHFCF2O-52-Cl-4-OCF2CHFO-52-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F7 | 93168-170157-159178-180160-161147-149183-1859095153-155188-189202-203104-105155-156198195181190-193219179204169-176 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
110111112113114115116117118119120121122123124125126127128129130131 | CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SO2CH3CH(CH3)CH2S-t-C4H9CH(CH3)CH2SO2-2-PyiCH(CH3)CH2SO2-2-PyiCH(C2H5)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SO2CH3C(CH3)2CH2SOCH3C(CH3)2CH2SOCH3CH(C2H5)(CH2)2SCH3CH(C2H5)(CH2)2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3 | 5-I5-I5-I3-Cl3-Cl6-Cl6-Cl3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-SCF33-SCF33-SOCF3 | 2-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-C2F52-CH3-4-C2F52-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F5 | 127-128143189189-19084-87102-103233-234252-25695-10092-93190194-196205-20688-9088-9074-7690-95170175201-203176-178183-185 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
132133134135136137138139140141142143144145146147148149150151152 | CH(CH3)CH2SCH3CH(CH3)(CH2)3SOCH3CH(CH3)(CH2)3SO2CH3CH(CH3)(CH2)3SOCH3CH(CH3)(CH2)3SO2CH3CH(Ph)CH2SOCH3CH(Ph)CH2SO2CH3CH(CH3)CH2SO2-t-C4H9C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SOCH3CH(CH3)CH2SOCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)(CH2)3SCH3CH(CH3)(CH2)3SCH3CH(CH3)(CH2)3SOCH3 | 3-SOCF33-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-Cl3-Cl3-I3-I3-Cl-4-F3-Cl-4-F3-Cl-4-F3-Cl6-Cl3-Cl | 2-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-OCF32-CH3-4-OCF32-CH3-4-OCF32-CH3-4-OCF32-CH3-4-C2F52-CH3-4-s-C4F92-CH3-4-i-C3F7-5-F2-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-C2F52-CH3-4-C2F5 | 154135163172-17520414220390-92172-173146-14786-88199-200152-155120210188-190203-204226-227124糊状物150 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
153154155156157158159160161162163164165166167168169170171172173 | CH(CH3)(CH2)3SO2CH3CH(CH3)(CH2)3SCH3CH(CH3)(CH2)3SCH3CH(CH3)(CH2)3SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)(CH2)2SCH3CH(CH3)(CH2)2SCH3CH(CH3)(CH2)2SCH3CH(CH3)(CH2)2SCH3CH(CH3)(CH2)2SCH3CH(CH3)(CH2)2SCH3CH(CH3)CH(CH3)SCH3CH(CH3)CH(CH3)SO2CH3CH(CH3)CH(CH3)SC2H5CH(CH3)CH(CH3)SO2C2H5C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2S02CH3C(CH3)2CH2SOCH3CH(CH3)(CH2)4SCH3 | 3-Cl3-Cl6-Cl3-Cl3-I3-OCH2-O-43-Cl3-Cl3-Cl3-I3-I3-I3-I3-I3-I3-I3-Cl3-Br3-Cl3-Cl3-I | 2-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-CF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-C2F5 | 117125糊状物115187110167-169169-171183-184192-194200-201193-194120130105105199-200200-2018690156 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
174175176177178179180181182183184185186187188189190191192 | CH(CH3)(CH2)4SCH3CH(CH3)(CH2)4SC2H5CH(CH3)(CH2)4SC2H5CH(CH3)(CH2)4SOC2H5CH(CH3)(CH2)4SOC2H5CH(CH3)(CH2)4SO2C2H5CH(CH3)(CH2)4SO2C2H5C(CH3)2CH2SO2CH3C(CH3)2CH2SOCH3C(CH3)2CH2SC2H5C(CH3)2CH2SOC2H5C(CH3)2CH2SC2H5C(CH3)2CH2SO2C2H5C(CH3)2CH2SC2H5CH(CH3)CH2S(CH2)2SCH3CH(CH3)CH2S(CH2)2SCH3CH(CH3)CH2S(CH2)2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3 | 3-I3-I3-I3-I3-I3-I3-I3-Br3-Br3-I3-I3-Cl3-Cl3-Br3-I3-I3-I3-SO2-CH36-SO2-CH3 | 2-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F7 | 17414716811512013114590-93212-213160-16278-82132-13468169-170169-171135-137159-161205-206210-212 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
193194195196197198199200201202203204205206207208209210211212 | CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)(CH2)2SOCH3CH(CH3)(CH2)2SO2CH3CH(CH3)(CH2)4SO2CH3CH(CH3)(CH2)4SO2CH3CH(CH3)(CH2)3SC2H5CH(CH3)(CH2)3SO2C2H5CH(CH3)(CH2)3SC2H5CH(CH3)(CH2)3SOC2H5CH(CH3)(CH2)3SO2C2H5Q1Q2CH(CH3)CH2SCH2CH=CH2CH2CH(CH3)SC2H5CH2CH(CH3)SO2C2H5CH2CH(CH3)SC2H5CH(CH3)CH2SCH3CH(CH3)(CH2)2SOCH3CH(CH3)(CH2)2SO2CH3 | 3,4-Cl23,4-Cl23-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I6-I3-OCF33-Cl3-Cl | 2-CH3-4-OCF32-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F7 | 198-201165-167123-125128-130145160143117150106117202249168-175150130155184-185无定形108-111 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
213214215216217218219220221222223224225226227228229230 | CH(CH3)(CH2)3SC2H5CH(CH3)(CH2)3SOC2H5CH(CH3)(CH2)3SO2C2H5(S)-C*H(CH3)CH2SCH3(R)-C*H(CH3)CH2SCH3C(CH3)2CH2SOC2H5C(CH3)2CH2S-n-C3H7C(CH3)2CH2SO-n-C3H7C(CH3)2CH2SO2-n-C3H7CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SO2CH3C(CH3)2(CH2)3SCH3C(CH3)2(CH2)2SCH3 | 3-Br3-Br3-Br3-I3-I3-Br3-I3-I3-I3-Cl-4-OCH33-NO23-NO23-I3-I3-Br3-Br3-I3-I | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF2CHFCF32-CH3-4-O-(3-Cl-5-CF3-2-Pyi2-Cl-4-OCF32-Cl-4-OCF32-Cl-4-OCF32-Cl-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F7 | 151159150212-214214-216107-110169-17088-9088-90122-125218188166141160133164108 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
231232233234235236237238239240241242243244245246247248249250251 | C(CH3)2(CH2)2CH(CH3)-SCH3C(CH3)2CH2SOCH3CH(CH3)CH2SCH3CH(CH3)CH2SO2CH3C(CH3)2CH2SC3H7-nC(CH3)2CH2SC3H7-nC(CH3)2CH2SO2C3H7-nC(CH3)2CH2SO2C3H7-nCH2CH(CH3)SCH3CH2CH(CH3)SO2CH3CH(CH3)CH2SO2CH3C(CH3)2CH2SC2H5CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SOCH3C(CH3)2CH2SC2H5C(CH3)2CH2SO2C2Hx5C(CH3)2CH2SOC2H5C(CH3)2CH2SO2C2H5C(CH3)2CH2SO2C2H5 | 3-I3-Br3-I3-I3-Br3-Cl3-Br3-Cl3-I3-I3-OCF33-I3,4-Cl23,4-Cl23-CF33-Cl3-I3-I3-I3-I3-I | 2-CH3-4-i-C3F72-Cl-4-OCF32-Cl-4-OCF32-Cl-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-Cl-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-C2F52-CH3-4-C2F52-CH3-4-OCF32-CH3-4-OCF3 | 151132172168162-163149-150176-180202-203200130226-228163138-139146-148209110-112188-189120-122125-126125(Rf=大)146(Rf=小) |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
252253254255256257258259260261262263264265266267268269270271272273 | C(CH3)2CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)(CH2)2SC2H5CH(CH3)(CH2)2SC2H5Q5Q6CH(CH3)CH2SOC2H5CH(CH3)CH2SO2C2H5CH(CH3)CH2SC2H5CH(CH3)CH2SOC2H5CH(CH3)CH2SO2C2H5CH(CH3)CH2SC2H5CH(CH3)CH2SOC2H5CH(CH3)CH2SO2C2H5CH(CH3)CH2SCH3CH(CH3)(CH2)2SOC2H5CH(CH3)(CH2)2SO2C2H5CH(CH3)CH2SC3H7-nC(CH3)2(CH2)2SC2H5Q7 | 3-OCH2O-43-OCF33-CF33-CF33-Cl3-I3-I3-I3-I3-I3-Br3-Br3-Br3-Cl3-Cl3-Cl3-Br3-I3-I3-Cl3-I3-I | 2-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-CF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F7 | 220220223199-201110-113173-17418314996981559613514592135170-172132-134108-110174171184 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
274275276277278279280281282283284285286287288289290291292 | CH(CH3)(CH2)2SOC2H5CH(CH3)(CH2)2SO2C2H5CH(CH3)CH2SCH3CH(CH3)CH2SO2CH3C(CH3)2CH2SCH3CH(CH3)CH2S-PyiC(CH3)2(CH2)3SC2H5C(CH3)2(CH2)3SCH3C(CH3)2(CH2)3SC2H5CH(CH3)CH2SO2CH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH2CF3CH(CH3)CH2S(CH2)2-OCOCF3CH(CH3)CH2S-C3H7-nCH(CH3)CH2SCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SOCH3C(CH3)2CH2SCH3 | 3-Cl3-Cl3-Cl3-Br3-OCF2O-43-I3-I3-Br,6-Br3-Br,6-Br3-Cl3-I3-I3-I3-Br3-OCF2O-43-OCF2O-43-OCF2O-43-OCF2O-43-OCF2O-4 | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-CF32-CH3-4-CF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-CF32-CH3-4-CF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-OCF32-CH3-4-OCF3 | 128-130105-106158-160118-120182126170111混合物121混合物179-181196-198216158-159111196223191187205 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
293294295296297298299300301302303304305306307308 | C(CH3)2CH2SO2CH3CH(CH3)CH2SOCH2CF3CH(CH3)CH2SO2CH2CF3CH(CH3)CH2S(CH2)2OHCH(CH3)CH2S(CH2)2-OC2H5CH2SCH3CH(CH3)CH2S-2-(3,5-(CH3)2-Pym)CH(CH3)CH2SO-2-(3,5-(CH3)2-Pym)CH(CH3)CH2SO2-2-(3,5-(CH3)2-Pym)CH(CH3)CH2SC(=S)-N(CH3)2CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3 | 3-OCF2O-43-I3-I3-I3-IH3-I3-I3-I3-I3-I3-I3-Cl3-Br3-I3-N=C(t-C4H9)O-4 | 2-CH3-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-3-C2F52-CH3-5-C2F52-CH3-4-CF32-CH3-4-CF32-CH3-4-CF32-CH3-4-i-C3F7 | 218207-209220-222157-159165-167157-159147-149126-128134-136糊状物223-225215-218179-181176-177184-186113 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
309310311312313314315316317318319320321322323324325326 | CH(CH3)CH2SC2H5C(CH3)2CH2SO2CH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2S(CH2)2-OCH3CH(CH3)CH2S(CH2)2-CO2CH3CH(CH3)CH2SO(CH2)2-OC2H5CH(CH3)CH2SO2(CH2)2-OC2H5CH(CH3)CH2S-BztC(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3 | 3-I3-Cl3-Br3-Br3-I3-I3-I3-I3-I3-I3-I3-Br3-Br3-NO23-NO23-NO23-NO23-NO2 | 2-CH3-4-CF32-CH3-4-CF32-CH3-4-CF32-CH3-4-CF32-CH3-4-CF32-CH3-4-CF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-OCF32-CH3-4-OCF32-Cl-4-CH32-CH3-4-Br2-CH3-4-i-C3F72,4-Cl2 | 193-194174-17585-88151-153102-104153-155154-155160-162116-118138-140179-181晶体178189204208234178 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
327328329330331332333334335336337338339340341 | C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3Q8CH(CH3)CH2SOCH3(CH2)2SHCH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SO(CH2)2-OCH3CH(CH3)CH2SO2(CH2)2-OCH3 | 3-NO23-NO23-I3-BrH4-CH=CH-CH=CH-53-CH=CH-CH=CH-43-CH=CH-CH=CH-43-CH=CH-CH=CH-43-CH=CH-CH=CH-43-Br3-Br3-Br3-I3-I | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF32-Cl-4-OCF32-Cl-4-OCF32-Cl-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F7 | 14319718311817015819411512118615517416490-93177-178 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
342343344345346347348349350351352353354355356357358 | CH(CH3)CH2SO(CH2)2-CO2CH3CH(CH3)CH2SO2(CH2)2-CO2CH3CH(CH3)CH2SO-2-BztCH(CH3)CH2SO2-2-BztCH(CH3)CH2SC2H5CH(CH3)CH2SC2H5CH(CH3)CH2SCH3CH(CH3)CH2SC2H5(CH2)2SC(=S)NHC2H5CH(CH3)CH2SCH3CH(CH3)CH2S-2-ThzCH(CH3)CH2S-2-(5-CH3-1,3,4-Thd)CH(CH3)CH2S-2-(5-CH3-1,3,4-Thd)C(CH3)2CH2SCH3C(CH3)2CH2SCH3CH(CH3)CH2SO2C2H5C(CH3)2CH2SO2CH3 | 3-I3-I3-I3-I3-OCF35-OCF33-CF33-CF3H3-OCF2CF2O-43-I3-I6-I3-OCF35-OCF33-OCF33-CF3 | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F7 | 144-147201-202133-135147-149189-190190-192220-221200-202129216180122-124148-150208-209225219-220159-161 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
359360361362363364365366367368369370371372373374 | CH(CH3)CH2SO2C2H5C(CH3)2CH2SO2CH3CH(CH3)CH2SCH2CO-N(C2H5)2CH(CH3)CH2SOCH2CO-N(C2H5)2CH(CH3)CH2SO2CH2CO-N(C2H5)2CH(CH3)CH2SO2-2-ThzC(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3 | 3-CF33-OCF33-I3-I3-I3-I3-I3-I3-I3-I3-Cl3-Cl3-Cl3-Cl-4-CH33-NO23-NO2 | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH2OH-4-i-C3F72-CH3-3-F-4-i-C3F72-CH3-4-n-C4F92-CH3-4-Si(CH3)32-Cl-4-OCF32-Cl-4-OCF32-Cl-4-OCF32-CH3-4-i-C3F72-CH3-4-C2F52-CH3-4-C2F5 | 218-219168-170130-13195-98197-199153-155188-191218-221170-174203-20715473149189218194 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
375376377378379380381382383384385386387388389390391392393 | C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SSCH3CH(CH3)CH2SS-(2-NO2-Ph)C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SOCH3CH(CH3)CH2SOCH3CH(CH3)CH2SOCH3CH(CH3)CH2SOCH3CH(CH3)CH2SHCH(CH3)CH2SCH3 | 3-NO23-NO23-NO23-NO23-Cl-4-CH33-Cl3-Cl3-Cl3-Cl3-Cl3-F3-F3-F3-NO23-NO23-NO23-NO23-I3-I | 2-CH3-4-C2F52-Cl-4-OCF32-Cl-4-OCF32-Cl-4-OCF32-CH3-4-i-C3F72-Cl-4-OCF32-Cl-4-OCF32-Cl-4-OCF32-CH3-4-i-C3F72-CH3-4-i-C3F72-Cl-4-OCF32-Cl-4-OCF32-Cl-4-OCF32-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-CF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF2-CHFOCF3 | 210181185186158-1591641721539291148102163218218243210226192-193 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
394395396397398399400401402403404405406407 | CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SC3H7-iC(CH3)2CH2SC4H9-tC(CH3)2CH2SOC4H9-tC(CH3)2CH2SOC3H7-iCH(CH3)CH2S-2-PyiCH(CH3)CH2SO-2-PyiCH(CH3)CH2SO2-2-PyiC(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3 | 3-I3-I3-I3-I3-13-I3-I3-I3-I3-Br3-Br3-Br3-I3-I | 2-CH3-4-OCF2-CHFOCF32-CH3-4-OCF2-CHFOCF32-CH3-4-OCF2-CHFOC3F7-n2-CH3-4-O-(3-Cl-5-CF3-2-Pyi)2-CH3-4-O-(3-Cl-5-CF3-2-Pyi)2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-O-(3-Cl-5-CF3-2-Pyi)2-CH3-4-O-(3-Cl-5-CF3-2-Pyi) | 206-208166-167175-176195-197180-18185-8895-98100-104100-1049313796105-108135-136 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
408409410411412413414415416417418419420421422 | CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3 | 3-I3-I3-I3-I3-I3-I3-Br3-Br3-Br3-I6-I3-I3-I3-I3-I | 2-CH3-4-OCF2-CHFOC3F7-n2-CH3-4-OCF2-CHFOC3F7-n2-CH3-4-O-(3-Cl-5-CF3-2-Pyi)2-CH3-4-O-(3-Cl-5-CF3-2-Pyi)2-CH3-3-F-4-i-C3F72-CH3-3-F-4-i-C3F72-C2H5-4-i-C3F72-Cl-4-C2F53-i-C3H72-CH3-4-OSO2CF32-CH3-4-OSO2CF32-CH3-4-OSO2CF32-CH3-4-OCF2-CHFOC3F7-n2-CH3-4-OCF2-CHFOC3F7-n2-CH3-4-OCF2-CHFOC3F7-n | 179-181196-198176-179199-201120-125206-210175180135187分解无定形170-17268-75170-172 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
423424425426427428429430431432433434435436437438439 | C(CH3)2CH2SC3H7-iC(CH3)2CH2SO2C3H7-iCH(CH3)CH2SC(=S)NH-CH3CH(CH3)CH2SC(=S)NH-C2H5CH(CH3)CH2SCONHC2H5CH(CH3)CH2SCOCH3CH(CH3)CH2SCH2C≡CHCH(CH3)CH2SCH2-(2,4-Cl2-Ph)C(CH3)2CH2S*OCH3(-)异构体C(CH3)2CH2S*OCH3(+)异构体C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2S-PhC(CH3)2CH2SO-Ph | 3-Br3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F73-CF2OCF2O-42-Cl-3-CF2OCF2O-42-C2H5-4-i-C3F72-C2H5-4-i-C3F72-C2H5-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F7 | 162-16370-75142123178117111140无定形[α]=-20.4无定形[α]=20.6205173188125166-167167-168107 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
440 | C(CH3)2CH2SO2-Ph | 3-I | 2-CH3-4-i-C3F7 | 200 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
441442443444445446447448449450451452453454455456 | C(CH3)2CH2S-2-PyiC(CH3)2CH2SO-2-PyiC(CH3)2CH2SO2-2-PyiC(CH3)2CH2SO2-2-PyiQ10Q11Q12C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH2-(4-Cl-Ph)CH(CH2OH)(CH2)2S-CH3C(CH3)2CH2SCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3 | 3-I3-I3-I6-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-NO23-NO2 | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-Cl-4-i-C3F72-Cl-4-i-C3F72-Cl-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-(4-Cl-Ph)2-CH3-4-(4-Cl-Ph )2-CH3-4-S(2-Cl-Ph)2-CH3-4-S(3-Cl-Ph) | 120-12290-95138219212-213193-213203-205184102-105200-201163-164102172128188181 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
457458459460461462463464465466467468469 | C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3CH(CH3)CH2SCON-(CH3)2CH(CH3)CH2SCON-(C2H5)2CH(CH3)CH2SCH2CO-CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3(S)-C*H(CH3)CH2S-C2H5C(CH3)2CH2SCH3C(CH3)2CH2SCH3 | 3-NO23-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH3-4-S(4-Cl-Ph)2-CH3-4-S(2-Cl-Ph)2-CH3-4-S(3-Cl-Ph)2-CH3-4-S(3-Cl-Ph)2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH(CH3)CH2CH-(CH3)2-4-i-C3F72-CH(CH3)CH2CH-(CH3)2-4-i-C3F72-CH(CH3)CH2CH-(CH3)2-4-i-C3F72-CH3-4-i-C3F72-CH3-4-(CO-(4-CH3-Ph))2-CH3-4-(CO-(4-Cl-Ph)) | 2011591561561177586178100-105157-158197138171 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
470471472473474475476477478479480481482483 | C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3 | 3-I3-I3-I3-I3-I3-I3-O(3-CF3-Ph)6-O(3-CF3-Ph)3-I3-I3-I3-I3-I3-I | 2-CH3-4-(C(=NOCH3)-(4-Cl-Ph))2-CH3-4-CH2(4-Cl-Ph)2-CH3-4-CH(OH)(4-Cl-Ph)2-CH3-4-O(4-Cl-Ph)2-CH3-4-O(3-Cl-Ph)2-CH3-4-O(3-CN-Ph)2-CH3-4-i-C3F72-CH3-4-i-C3F74-SO2N(C2H5)22-CH3-4-(CONH(4-Cl-Ph))2-CH3-4-(CON(CH3)-(4-Cl-Ph))2-CH3-4-C(CF3)2OCH32-CH3-4-C(CF3)2OCH32-CH3-4-C(CF3)2OCH3 | 糊状物162糊状物179170176169-170167-169207-208236149195-196178-180205-206 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
484485486487488489490491492493494495496497 | C(CH3)2CH2SCH2C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3 | 3-IH3-I3-IHH3-I3-I3-I3-I3-I3-I3-I3,4-Cl2 | 2-CH3-4-C(CF3)2-OCH2-Ph4-CF32-CH3-4-C(CF3)2OH4-NHSO2CF34-CF34-CF32-CH3-4-(C(=NOH)-(4-Cl-Ph))2-CH3-4-C(CF3)2S-CH32-CH3-4-C(CF3)2O-CH2Ph2-CH3-4-C(CF3)2O-CH2Ph2-CH3-4-(CON-(C2H5)2)2-CH3-4-(CON-(CH3)22-CH3-4-(CF3)2O-C2H52-CH3-4-i-C3F7 | 149-151185-188143-145207-209226-227192-194112163-164150-152125-126187无定形185-186 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
498499500501502503504505506507508509510 | C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH2OCH3)CH2S-CH3CH(CH2OCH3)CH2-SOCH3CH(CH2OCH3)CH2-SO2CH3CH(CF3)CH2SCH3CH(CH2SCH3)CH2-COOCH3CH(CH2SCH3)CH2-CONHCH3CH(CH2SCH3)CH2-CON(CH3)2C(CH3)2CH2S-C3H5-cC(CH3)2CH2SO-C3H5-cC(CH3)2CH2SO2-C3H5-cQ13 | 3,4-Cl23,4-Cl23-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F7 |
表1(续)
序号 | T1 | (X)l | (Y)m | 性质mp(℃) |
511512513514515516517518519520521522523524523 | Q16Q14Q15C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2S(=O)-OCH3C(CH3)2CH2SO3CH3C(CH3)2CH2SO2-NHCH3C(CH3)2CH2SO2-NHC2H5C(CH3)2CH2SO2-N(CH3)2C(CH3)2CH2SO2-N(C2H5)2 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-(4-CF3-Ph)2-CH3-4-(4-CF3-Ph)2-CH3-4-(4-CF3-Ph)2-CH3-4-OCF2CF32-CH3-4-OCF2CF32-CH3-4-OCF2CF32-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F7 |
表2(R3=H)
序号 | T1 | R2 | (X)l | (Y)m | 性质mp(℃) |
2-12-22-32-42-52-62-72-82-92-102-112-12 | (CH2)2SC2H5(CH2)2SCH3(CH2)2SCH3(CH2)2SO2CH3(CH2)2SCH3(CH2)3SCH3(CH2)2SCH3CH2SCH3(CH2)2SOCH3(CH2)2SO2CH3(CH2)2SOCH3(CH2)2SO2CH3 | n-C3H7n-C3H7n-C3H7n-C3H7C2H5C2H5CH3C2H5CH3CH3C2H5C2H5 | HH3-F3-F3-F3-F3-F3-Cl3-F3-F3-F3-F | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F7 | 糊状物12212481132-137120-122127-132155-159糊状物160-164糊状物糊状物 |
表2(续)
序号 | T1 | R2 | (X)l | (Y)m | 性质mp(℃) |
2-132-142-152-162-17 | (CH2)3SOCH3(CH2)3SO2CH3CH(CH3)CH2SCH3CH2SCH3CH2SCH3 | C2H5C2H5C2H5C2H5C2H5 | 3-F3-F3-F3-Cl3-Cl | 2-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-i-C3F72-CH3-4-OCF3折射率nD1.54402-CH3-4-OC2F5折射率nD1.5365 | 糊状物173114(21.0℃)(21.0℃) |
通式(1)
表3(R2=R3=H)
序号 | T2 | (X)l | (Y)m | 性质mp(℃) |
3-13-23-33-43-53-6 | Q3Q3Q4Q4Q4Q9 | 3-I3-I3-I3-I3-I3-I | 2-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-OCF32-CH3-4-C2F52-CH3-4-i-C3F72-CH3-4-i-C3F7 | 163144173-175158-160186-188195-197 |
在表1至3中,“Ph”意为苯基;“Pyi”意为吡啶基;“Pym”意为嘧啶基;“Thz”意为噻唑基;“Thd”意为噻二唑基;“Bzt”意为苯并噻唑基;“c-”意为脂环族烃基;和Q1,Q2,Q3,Q4,Q5,Q6,Q7,Q8,Q9,Q10,Q11,Q12,Q13,Q14,Q15和Q16代表下述化合物:
在表1,2和3中,一些化合物表现出糊状物的性质。此类化合物的1H-NRM数据在表4中说明。
表4
序号 | 1H-NMR[CDCl3/TMS,δ值(ppm)] |
2 | 0.8-1.4(m.9H),2.4(s.3H),2.5-2.8(m.3H),4.3(m.1H),6.2(d.1H),7.2-7.5(m.3H),7.8(d.1H),8.0(d.1H),8.4(d.1H),8.5(s.1H). |
含有本发明通式(I)的邻苯二酰胺衍生物或其盐作为活性成分的农业园艺用杀虫剂适合防治各种对水稻、果树、蔬菜、其它作物、花卉和观赏植物等有害的害虫如农业害虫、森林害虫、园艺害虫、储藏谷物害虫、卫生害虫、线虫等。它们具有明显的杀虫效果,例如对鳞翅目(Lepidoptera),包括苹果小卷叶蛾(
Adoxophyes
orana fasciata)、茶小卷叶蛾(
Adoxophyes
sp.),苹果小食心虫(
Grapholita inopinata),梨小食心虫(
Grapholita
molesta),大豆食心虫(
Leguminivora
glycinivorella),桑卷叶蛾(
Olethreutesmori),茶细蛾(
Caloptiliathevivora),潜叶细蛾属(
Calopilia
zachrysa),金纹细蛾(
Phyllonorycter
ringoniella),梨潜皮蛾(
Spulerrina astaurota),菜粉蝶(
Piers
rapae
crucivora),棉铃虫(
Heliothis sp.),苹果蠹蛾(
Laspey
resia
pomonella),菜蛾(
Plutella xylostella),苹实巢蛾(
Argyresthia
conjugella),桃小食心虫(
Carposina
niponensis),二化螟(
Chilo
suppressalis),稻纵卷叶螟(
Cnaphalocrocis
medinalis),烟草螟(
Ephestia
elutella),桑螟(
Glyphodes
pyloalis),三化螟(
Scirpophaga
incertulas),直纹稻苞虫(
Parnara
guttata),东方粘虫(
Pseudaletia
separata),大螟(
Sesamia
inferens),斜纹夜蛾(
Spodoptera
litura),甜菜夜蛾(
Spodoptera
exigua)等;半翅目,包括紫菀叶蝉(
Macrosteles fascifrons),黑尾叶蝉(
Nephotettix
cincticeps),稻褐飞虱(
Nilaparvata
lugens),白背飞虱(
Sogatella
furcifera),桔木虱(
Diaphorina
citri),葡萄粉虱(
Aleurolobus
taonabae),棉粉虱(
Bemisia
tabaci),温室粉虱(
Trialeurodes vaporariorum),菜缢管蚜(
Lipaphis
erysimi),桃蚜(
Myzus
persicae),印度蜡蚧(
Ceroplastes
ceriferus),黄绿絮蚧(
Pulvinaria
aurantii),樟圆蚧(
Pseudaonidia
duplex),梨圆蚧(
Comstockaspis
perniciosa),矢尖蚧(
Unaspis
yanonensis)等;线虫(
Tylenchida),包括草地垫刃线虫属(
Pratylenchus
sp.),方头绿金龟子(
Anomala
rufocuprea),日本金龟子(
Popillia
japonica),烟草窃蠹(
Lasioderma serricorne),欧洲竹粉蠹(
Lyctus
brunneus),二十八星瓢虫(
Epilachna
vigintiotopunctata),绿豆象(
Callosobruchus chinensis),蔬菜象虫(
Listroderes
costirostris),玉米象(
Sitophilus
zeamais),棉铃象鼻虫(
Authonomus
gradis
gradis),稻象甲(
Lissorhoptrus
oryzophilus),黄守瓜(
Aulacophora femoralis),稻负泥虫(
Oulema
oryzae),黄曲条跳甲(
Phyllotreta striolata),松纵坑梢小蠹(
Tomicus
piniperda),马铃薯甲虫(
Leptinotarsa
decemlineata),墨西哥豆瓢虫(
Epilachna varivestis),玉米根叶甲(
Diabrotica
sp.)等;双翅目(Diptera),包括瓜实蝇(
Dacus(Zeugodacus)
cucurbitae),桔小实蝇(
Dacus (Bactrocera)
dorsalis),稻潜蝇(
Agnomyza
oryzae),葱蝇(
Delia
antigua),种蝇(
Delia
platura),大豆夹瘿蝇(
Asphondylia sp.),家蝇(
Musca
domestica),库蚊(
Culex
pipiens
pipiens)等;和垫刃线虫(Tylenchida),包括咖啡游离根线虫(
Pratylenchus coffeae),马铃薯囊线虫(
Globodera
rostochiensis),根结线虫(
Meloidogyne
sp.),柑桔根线虫(
Tylenchulus
semipenetrans),滑刃小杆线虫属(
Aphelenchus
avenae),滑刃线虫(
Aphelenchoides ritzemabosi)等。
含有本发明通式(I)的邻苯二酰胺衍生物或其盐作为活性成分的农用或园艺用杀虫剂对对水田作物、旱田作物、果树、蔬菜、其它作物、花卉和观赏植物等有害的上述害虫、卫生害虫和/或线虫具有明显的杀虫效果。因此,在害虫、卫生害虫或线虫预期出现、在其出现前或确定其出现时的季节,向水田;旱田;作物如果树、蔬菜、观赏植物等;植物本身的种子、花卉、茎、叶等;植物生长的环境如水田水、土壤等使用本发明农用或园艺用杀虫剂可获得所需效果。
通常,本发明的农用和园艺用杀虫剂在根据制备农用化学品的常规方法制成可方便使用的形式后使用。
即,通式(I)的邻苯二酰胺衍生物或其盐和任选的助剂以一定比例与合适的惰性载体混合,通过溶解、分散、悬浮、混合、浸渍、吸附或粘着制成合适的制剂形式如悬浮剂、乳油、可溶性浓缩物、可湿性粉剂、颗粒剂、粉剂或片剂。
在本发明中使用的惰性载体可为固体或液体。固体载体的实例为大豆粉、谷粉、木粉、树皮粉、锯末、烟草茎粉、胡桃壳粉、麸糠、纤维素粉末、蔬菜提取残留物、合成聚合物或树脂粉、粘土(例如高岭土、膨润土和酸性粘土),滑石(例如滑石和叶蜡石),二氧化硅粉或絮片(例如硅藻土、硅石砂、云母和白碳黑,即合成的高分散硅酸,也称细分散的水合二氧化硅或水合硅酸,一些市售产品含有硅酸钙作为主要组分),活性碳、硫粉、浮石粉、煅烧硅藻土、碎砖、飘尘、沙子、碳酸钙粉、磷酸钙粉和其它无机或矿物粉、化肥(例如硫酸铵、磷酸铵、硝酸铵、尿素和氯化铵)和堆肥。这些载体可以单独使用或以混合物形式使用。
液体载体材料是本身具有溶解性,或不具备溶解性但能够借助助剂分散活性成分的那些。下面是液体载体的典型例子,它们可单独或混合使用:水;醇类如甲醇、乙醇、异丙醇、丁醇和乙二醇;酮类如丙酮、甲基乙基酮、甲基异丁基酮、二异丁基酮和环己酮;醚类如乙醚、二烷、溶纤剂、二丙基醚和四氢呋喃;脂族烃如煤油和矿物油;芳烃如苯、甲苯、二甲苯、溶剂石脑油和烷基萘;卤代烃如二氯乙烷、氯仿、四氯化碳和氯苯;酯类如乙酸乙酯、邻苯二甲酸二异丙酯、邻苯二甲酸二丁基酯和邻苯二甲酸二辛基酯;酰胺如二甲基酰胺、二乙基甲酰胺和二甲基乙酰胺;腈类如乙腈;和二甲基亚砜。
下述是助剂的典型实例,助剂是根据目的使用的,且在一些情况下可单独或结合使用,或根本不需要使用助剂。
为了乳化、分散、溶解和/或湿润活性成分,使用表面活性剂。表面活性剂例如有聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯高级脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脱水山梨醇单月桂酸酯、聚氧乙烯脱水山梨醇单油酸酯、烷基芳基磺酸盐、萘磺酸缩合产物、木质素磺酸盐和高级醇硫酸酯。
此外,为了稳定活性成分的分散液,粘着活性成分和/或粘结活性成分,可使用助剂如酪蛋白、明胶、淀粉、甲基纤维素、羧甲基纤维素、阿拉伯胶、聚乙烯醇、松节油、米糠油、膨润土和木质素磺酸盐。
为了改善固体产物的流动性,可使用助剂如蜡、硬脂酸酯和磷酸烷基酯。
如萘磺酸缩合产物和磷酸酯缩聚物的助剂可用作可分散产品的胶溶剂。
如硅油的助剂也可用作消泡剂。
活性成分的含量可以根据需要而变化,且可在0.01至80%重量的范围内选择。在粉剂或颗粒剂中,其合适的含量为0.01至50%重量。在乳油或可流动可湿性粉剂中,合适的含量也是0.01至50%重量。
本发明的农用和园艺用杀虫剂可以下述方式用来防治多种害虫。即,将其直接或适当地用水稀释或悬浮在水中后,以防治害虫的有效量施用到预期出现害虫的作物或不希望出现害虫的场所。
本发明的农用和园艺用杀虫剂的使用剂量根据多种因素变化,如使用目的、防治的害虫、植物的生长状态、害虫出现的趋势、气候、环境条件、制剂形式、使用方法、施用场所和使用时间。根据使用目的,一般选择每10公亩(are)0.1g-10kg(以活性成分计)。
根据使用本发明农用和园艺用杀虫剂的场合,为了扩大病害防治谱和所防治害虫的种类以及可有效施药的时期或为了降低剂量,本发明的农用和园艺用杀虫剂可与其它农业和园艺病害或害虫防治剂、杀螨剂、杀线虫剂、生物农药等;和除草剂、植物生长调节剂、肥料等混合使用。
通过向水稻苗床、种子等施药的方法,或通过种子消毒的方法,本发明农业园艺用杀虫剂可被施用到植物种子或育种的栽培介质如育种的土壤、培养秧苗的垫,水中等。为了防治在果树、谷物、种植蔬菜的旱田等上产生的害虫,还可通过种子处理如包粉、浸渍等方法,灌溉秧苗生长的载体如培育秧苗的容器、种植植物的孔穴等,或通过处理水配植物的培育液而使植物吸收本发明的农业园艺用试剂。
下面提供本发明典型的实施例。这些实施例不构成对本发明的限制。
实施例1
(1-1)制备N-[4-(1,1,2,3,3,3-六氟丙氧基)-1-甲基苯基]-3-硝基苯邻二甲酰亚胺
在30ml乙酸中溶解1.93g的3-硝基邻苯二甲酸酐和2.73g的4-(1,1,2,3,3,3-六氟丙氧基)-1-甲基苯胺。在加热回流条件下进行反应3小时。反应完成后,在减压条件下蒸馏掉溶剂,用乙醚和己烷的混合物洗涤剩余物,因此得到了4.4g目标化合物。
性质:熔点121℃;产率98%。
(1-2)制备N1-[4-(1,1,2,3,3,3-六氟丙氧基)-1-甲基苯基]-N2-(1-甲基-2-甲硫基乙基)-3-硝基邻苯二酰胺(化合物号223)
在10ml二烷中溶解0.54g的N-[4-(1,1,2,3,3,3-六氟丙氧基)-1-甲基苯基]-3-硝基苯邻二甲酰亚胺。然后向上述制备的溶液中加入0.25g的1-甲基-2-甲硫基乙基胺和0.01g乙酸。在加热回流条件下进行反应3小时。反应完成后,在减压条件下蒸馏掉溶剂,剩余物通过柱色谱纯化,使用1/1己烷和乙酸乙酯的混合物作为洗脱剂。因此得到0.45g目标化合物,其Rf值为0.4至0.5。
性质:熔点218℃;产率68%。
实施例2
(2-1)制备3-氟-N-(4-七氟异丙基-2-甲基苯基)苯邻二甲酰亚胺
在10ml乙酸中溶解1.33g的3-氟邻苯二甲酸酐和2.73g的4-七氟异丙基-2-甲基苯胺。在加热回流条件下进行反应3小时。反应完成后,在减压条件下蒸馏掉溶剂,用乙醚和己烷的混合物洗涤剩余物,得到了3.1g目标化合物。
性质:熔点155-157℃;产率97%。
(2-2)制备N-(七氟异丙基-2-甲基苯基)苯邻二甲酰亚胺
在20ml二甲基甲酰胺中溶解2.54g的3-氟-N-(4-七氟异丙基-2-甲基苯基)苯邻二甲酰亚胺。然后向上述制备的溶液中加入2.8g的15%甲硫醇水溶液,在室温下进行反应3小时。反应完成后,将反应溶液倒入水中,并用乙酸乙酯萃取目标产物。用无水镁干燥萃取溶液,在减压条件下蒸馏掉溶剂,剩余物用乙醚和己烷的混合物洗涤。因此得到2.2g目标化合物。
性质:熔点163-165℃;产率81%。
(2-3)制备N-(4-七氟异丙基-2-甲基苯基)-3-甲基磺酰基苯邻二甲酰亚胺
在20ml二氯甲烷中溶解0.63g的N-(4-七氟异丙基-2-甲基苯基)-3-甲硫基苯邻二甲酰亚胺。用冰冷却该溶液,加入0.58g间氯过苯甲酸,并在室温下反应。反应完成后,将反应溶液倒入水中,用氯萃萃取目标产物。有机层用硫代硫酸钠和碳酸钾的水溶液洗涤,用无水镁干燥,在减压条件下蒸馏掉溶剂,用乙醚和己烷的混合物洗涤剩余物,因此得到了0.63g目标化合物。
性质:熔点185-187℃;产率93%。
(2-4)制备N1-[4-七氟异丙基-2-甲基苯基]-N2-(1-甲基-2-甲硫基乙基)-3-甲基磺酰基邻苯二酰胺(化合物号191)和N1-[4-七氟异丙基-2-甲基苯基]-N2-(1-甲基-2-甲硫基乙基)-6-甲基磺酰基邻苯二酰胺(化合物号192)
在10ml二烷中溶解0.63g的N-(4-七氟异丙基-2-甲基苯基)-3-甲基磺酰基苯邻二甲酰亚胺。然后向上述制备的溶液中加入0.25g的1-甲基-2-甲硫基乙基胺和0.01g乙酸。在加热回流条件下进行反应3小时。反应完成后,在减压条件下蒸馏掉溶剂,剩余物通过硅胶柱色谱纯化,使用1/1己烷和乙酸乙酯的混合物作为洗脱剂。由此得到0.42g第一种目标化合物,其Rf值为0.5至0.7(化合物号191)和0.18g的第二种目标化合物,其Rf值为0.2至0.3(化合物号192)。
化合物号191:性质:熔点205-206℃;产率55%。
化合物号192:性质:熔点210-212℃;产率24%
实施例3
(3-1)制备3-碘-N-(1-甲基-3-甲硫基丙基)邻氨甲酰苯甲酸
在用冰冷却的2.74g 3-碘邻苯二甲酸酐的8ml乙腈悬浮液中慢慢滴加1.19g的1-甲基-3-甲硫基丙基胺的3ml乙腈溶液。滴加完后,伴随搅拌,使反应在室温下进行3小时。反应完成后,过滤收集沉淀结晶,并用少量的乙腈洗涤。由此得到了3.5g目标化合物。
性质:熔点148-150℃;产率89%。
(3-2)制备6-碘-N-(1-甲基-3-甲硫基丙基)苯邻二甲酰异亚胺(phthalisoimide)
在0.79g的3-碘-N-(1-甲基-3-甲硫基丙基)邻氨甲酰苯甲酸的10ml甲苯悬浮液中加入0.63g的三氟乙酸酐。伴随搅拌使反应在室温下进行30分钟。反应完成后,减压下蒸馏掉溶剂,获得0.75g粗目标粗产物,不需要进一步提纯,即可用到随后的反应中。
(3-3)制备6-碘-N1-(4-七氟异丙基-2-甲基苯基)-N2-(1-甲基-3-甲硫基丙基)邻苯二酰胺(化合物号162)
在10ml乙腈中溶解0.75g的6-碘-N-(1-甲基-3-甲硫基丙基)苯邻二甲酰异亚胺。向上述溶液中加入0.55g的4-七氟异丙基-2-甲基苯胺和0.01g的三氟乙酸,伴随搅拌进行反应3小时。反应完成后,过滤收集沉淀结晶,并用少量冷乙腈洗涤。因此得到了1.17g目标化合物。
性质:熔点192-194℃;产率90%。
(3-4)制备3-碘-N1-[4-七氟异丙基-2-甲基苯基]-N2-(1-甲基-3-甲基亚磺酰基丙基)邻苯二酰胺(化合物号195)
在10ml二氯甲烷中溶解0.65g的6-碘-N1-(4-七氟异丙基-2-甲基苯基)-N2-(1-甲基-3-甲硫基丙基)邻苯二酰胺。然后向上述制备的溶液中加入0.18g的间氯过苯甲酸,在室温下进行反应3小时。反应完成后,将反应溶液倒入水中,并用氯仿萃取目标产物。用硫代硫酸钠水溶液和碳酸钾水溶液洗涤有机层,用无水硫酸镁干燥,在减压条件下蒸馏掉溶剂,剩余物用乙醚和己烷的混合物洗涤。由此得到0.61g目标化合物。
性质:熔点123-125℃;产率92%。
(3-5)制备3-碘-N1-[4-七氟异丙基-2-甲基苯基]-N2-(1-甲基-3-甲基磺酰基丙基)邻苯二酰胺(化合物号196)
如实施例(3-4)中所述的相同方法处理3-碘-N1-[4-七氟异丙基-2-甲基苯基]-N2-(1-甲基-3-甲基亚磺酰基丙基)邻苯二酰胺(0.4g)。由此得到0.39g目标化合物。
性质:熔点128-130℃;产率95%。
实施例4
(4-1)制备N-(4-七氟异丙基-2-甲基苯基)-3-三氟甲氧基苯甲酰胺
在50ml四氢呋喃中溶解2.24g 3-三氟甲氧基苯甲酰氯,向其中缓慢滴加入2.75g的4-七氟异丙基-2-甲基苯胺和1.2g的三乙胺。滴加完后,在室温下进行反应1小时。反应完成后,将反应溶液倒入水中,用乙酸乙酯萃取目标产物,用无水硫酸镁干燥,减压条件下蒸馏掉溶剂,剩余物用乙醚和己烷的混合物洗涤。由此获得4.6g目标化合物。
性质:油状产物;产率99%。
(4-2)制备N-(4-七氟异丙基-2-甲基苯基)-3-三氟甲氧基邻氨甲酰苯甲酸
在20ml四氢呋喃中,溶解2.2g的N-(4-七氟异丙基-2-甲基苯基)-3-三氟甲氧基苯甲酰胺。在-70℃,将10ml仲丁基锂(0.96gM/L)缓慢加入到上述溶液中,在室温下反应30分钟。然后移去冷却浴,将过量的二氧化碳引入反应溶液,并在室温下反应30分钟。反应完成后,将反应溶液倒入水中,用稀盐酸酸化,用乙酸乙酯萃取目标产物,并用无水硫酸镁干燥,在减压下蒸馏掉溶剂,剩余物用乙醚和己烷的混合物洗涤。由此获得2.1g目标化合物。
性质:熔点:168-172℃;产率:87%
(4-3)制备N-(4-七氟异丙基-2-甲基苯基)-3-三氟甲氧基苯邻二甲酰异亚胺
向在10ml甲苯中的0.46gN-(4-七氟异丙基-2-甲基苯基)-3-三氟甲氧基邻氨甲酰苯甲酸的悬浮液中,加入0.51g的三氟乙酸酐,并在室温下进行反应30分钟。反应完成后,在减压条件下蒸馏掉溶剂,获得0.49g的目标粗产物。不需要纯化,将由此获得的产物使用到随后的反应中。
(4-4)制备N1-[4-七氟异丙基-2-甲基苯基]-N2-3-(1-甲基-2-甲硫基乙基)-3-三氟甲氧基邻苯二酰胺(化合物号210)
在10ml乙腈中溶解0.44g N-(4-七氟异丙基-2-甲基苯基)-3-三氟甲氧基苯邻二甲酰异亚胺。然后,向所得溶液中加入0.10g的1-甲基-2-甲硫基苯胺和0.10g的三氟乙酸,并反应3小时。反应完成后,将反应溶液冷却至0℃,过滤收集沉淀结晶,并用己烷洗涤。由此得到0.46g目标化合物。
性质:熔点184-185℃;产率77%。
下面描述本发明典型的制剂实施例和测试实施例。这些实施例不构成对本发明的任何限制。
在制剂实施例中,术语“份”意为“重量份”。
制剂实施例1
在表1,2或3中例举的各化合物 50份
二甲苯 40份
聚氧乙烯壬基苯基醚和烷基苯磺酸钙的混合物 10份
通过均匀混合上述成分以使之溶解而制备乳油。
制剂实施例2
在表1,2或3中例举的各化合物 3份
粘土粉 82份
硅藻土粉末 15份
通过均匀混合并研磨上述成分制备粉剂。
制剂实施例3
在表1,2或3中例举的各化合物 5份
膨润土和粘土的混合粉 90份
木质素磺酸钙 5份
通过均匀混合上述成分,并与适当量的水一起捏制所得混合物,接着造粒并干燥制备颗粒剂。
制剂实施例4
在表1,2或3中例举的各化合物 20份
高岭土和合成高分散硅酸混合物 75份
聚氧乙烯壬基苯基醚和烷基苯磺酸钙的混合物 5份
通过均匀混合并研磨上述成分制备可湿性粉剂。
测试实施例1:对菜蛾(
Plutella
xylostella)的杀虫效果
将菜蛾成虫释放,并使之在小白菜苗上产卵。释放两天后,将带有卵的小白菜苗在液体化学品中浸泡约30秒,上述液体是通过稀释含有在表1,2或3中例举的各化合物作为活性成分的制剂而制备的,调节浓度至50ppm。晾干后,将其放置在25℃恒温的室内。浸渍六天后,计数孵化的昆虫。根据下述公式计算死亡率,根据下示标准评价杀虫效果。每个试验进行3组重复,每组10只昆虫。
标准:
效果
死亡率(%)
A 100
B 99-90
C 89-80
D 79-50
试验结果示于表5。
测试实施例2:对斜纹夜蛾(
Spodoptera
litura)的杀虫效果
将一片甘蓝叶(品种:Shikidori)浸渍在通过稀释含有在表1,2或3中例举的各化合物作为活性成分的制剂而制备的液体化学品中约30秒,调节浓度至50ppm。晾干后,将其放置在直径9cm的塑料陪替氏培养皿中,用斜纹夜蛾的二龄幼虫接种,然后盖上培养皿,放置在25℃恒温的室内。接种八天后,计数死亡和存活虫数。根据下述公式计算死亡率,根据测试实施例1中所示的标准评价杀虫效果。每个试验进行3组重复,每组10只昆虫。
试验结果示于表5。
测试实施例3:对茶小卷叶蛾(
Adoxophyes
sp.)的杀虫效果
将一片茶树叶浸渍在含有在表1,2或3中例举的各化合物作为活性成分的液体化学品中30秒,调节浓度至50ppm。晾干后,将叶片移至直径9cm的塑料培养皿中,用茶小卷叶蛾幼虫接种。然后将叶片放置在25℃恒温,湿度70%的室内。接种八天后,计数死亡和存活数。根据测试实施例1中所述的相同标准评价杀虫效果。每个试验进行3组重复,每组10只昆虫。
试验结果示于表5。
表5
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
1 | A | A | A |
2 | A | A | A |
3 | A | A | A |
4 | A | ||
5 | A | A | |
6 | A | A | A |
7 | A | A | A |
8 | A | C | |
9 | A | ||
10 | A | A | A |
11 | A | A | A |
12 | A | ||
13 | A | ||
14 | A | ||
15 | A | ||
16 | A | A | |
17 | A | A | A |
18 | A | A | A |
19 | A | A | A |
20 | A | A | A |
21 | A | A | A |
22 | A | A | A |
23 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
24 | A | A | |
25 | A | A | A |
26 | A | A | A |
27 | A | ||
28 | A | A | A |
29 | A | A | A |
30 | A | A | A |
31 | A | A | A |
32 | A | A | A |
33 | A | A | A |
34 | A | A | A |
35 | A | A | A |
36 | A | ||
37 | A | A | A |
38 | A | A | |
39 | A | A | A |
41 | A | A | A |
42 | A | ||
43 | A | A | |
44 | A | A | |
46 | A | A | |
47 | A | ||
48 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
49 | A | A | A |
50 | A | A | A |
51 | A | ||
52 | A | ||
53 | A | A | |
54 | A | C | A |
55 | A | ||
56 | A | A | A |
57 | A | A | |
58 | A | ||
59 | A | A | |
60 | A | A | |
61 | A | A | A |
62 | A | A | A |
63 | A | A | |
64 | A | A | |
65 | A | A | A |
66 | A | A | A |
67 | A | A | A |
71 | A | ||
72 | A | A | |
73 | A | C | A |
74 | A | D |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
75 | A | A | A |
76 | A | A | A |
77 | A | ||
78 | A | ||
79 | A | A | A |
80 | A | A | A |
81 | A | A | A |
82 | A | A | |
83 | A | A | A |
84 | A | A | A |
85 | A | A | |
86 | A | A | A |
87 | A | C | |
88 | A | C | |
89 | A | A | |
90 | A | A | |
92 | A | A | A |
93 | A | A | A |
94 | A | A | A |
95 | A | A | A |
96 | A | A | A |
97 | A | A | A |
98 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
99 | A | A | A |
100 | A | C | A |
101 | A | A | A |
102 | A | A | |
103 | A | ||
104 | A | ||
105 | A | A | |
106 | A | A | A |
107 | A | ||
108 | A | A | |
109 | A | A | A |
110 | A | ||
111 | A | B | |
112 | A | A | A |
113 | A | A | A |
114 | A | A | A |
115 | A | A | |
116 | A | ||
117 | A | A | |
118 | A | A | A |
119 | A | A | A |
120 | A | ||
121 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
122 | A | A | A |
123 | A | A | A |
124 | A | A | A |
125 | A | A | A |
126 | A | A | A |
127 | A | A | A |
129 | A | ||
130 | A | A | A |
132 | A | ||
133 | A | A | |
134 | A | A | A |
135 | A | A | A |
136 | A | A | A |
137 | A | A | |
139 | A | A | |
140 | A | A | A |
141 | A | A | |
142 | A | A | A |
143 | A | D | |
144 | A | A | |
145 | A | A | A |
146 | A | A | A |
147 | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
148 | A | C | |
149 | A | A | |
150 | A | A | A |
151 | A | ||
152 | A | ||
153 | A | A | A |
154 | A | A | A |
155 | A | A | |
156 | A | A | A |
157 | A | A | A |
158 | A | ||
159 | A | A | A |
160 | A | A | A |
161 | A | A | A |
162 | A | A | A |
163 | A | A | A |
164 | A | A | |
165 | A | A | A |
166 | A | A | A |
167 | A | A | A |
168 | A | A | A |
169 | A | A | A |
170 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
171 | A | A | |
172 | A | ||
173 | A | A | A |
174 | A | C | A |
175 | A | D | A |
176 | A | A | A |
177 | A | ||
178 | A | D | A |
179 | A | A | |
180 | A | A | |
181 | A | A | A |
182 | A | A | A |
183 | A | A | A |
184 | A | A | A |
185 | A | A | A |
186 | A | A | A |
187 | A | A | A |
188 | A | A | A |
189 | A | A | A |
190 | A | A | |
191 | A | A | A |
192 | A | ||
193 | A | D |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
194 | A | ||
195 | A | A | A |
196 | A | A | A |
197 | A | C | A |
198 | A | A | A |
199 | A | A | A |
200 | A | A | A |
201 | A | A | A |
202 | A | A | |
203 | A | A | A |
204 | A | A | A |
205 | A | A | A |
206 | A | A | A |
207 | A | A | A |
208 | A | A | A |
209 | A | ||
210 | A | A | A |
211 | A | A | A |
212 | A | A | A |
213 | A | A | A |
214 | A | ||
215 | A | A | |
216 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
217 | A | A | A |
218 | A | A | A |
219 | A | A | A |
220 | A | A | A |
221 | A | A | A |
222 | A | ||
223 | A | ||
224 | A | A | |
225 | A | A | A |
226 | A | A | A |
227 | A | A | |
228 | A | A | |
229 | A | A | A |
230 | A | A | A |
231 | A | A | A |
232 | A | A | |
233 | A | A | |
234 | A | A | A |
235 | A | A | A |
236 | A | A | A |
237 | A | A | A |
238 | A | A | A |
239 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
240 | A | A | A |
241 | A | A | A |
242 | A | A | A |
243 | A | A | A |
244 | A | A | A |
245 | A | A | A |
246 | A | A | A |
247 | A | A | A |
248 | A | A | A |
249 | A | A | A |
250 | A | A | |
251 | A | A | |
252 | A | A | |
253 | A | A | A |
254 | A | A | A |
255 | A | A | A |
256 | A | A | A |
257 | A | A | A |
258 | A | ||
259 | A | A | A |
260 | A | A | A |
261 | A | A | A |
262 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
263 | A | A | A |
264 | A | A | A |
265 | A | A | A |
266 | A | A | A |
267 | A | A | A |
268 | A | A | A |
269 | A | A | A |
270 | A | A | A |
271 | A | C | A |
272 | A | A | A |
273 | A | C | |
274 | A | C | A |
275 | A | ||
276 | A | A | A |
277 | A | ||
278 | A | A | A |
279 | A | C | |
280 | A | C | A |
281 | A | A | A |
282 | A | A | A |
283 | A | A | A |
284 | A | A | A |
285 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
286 | A | C | A |
287 | A | A | A |
288 | A | A | A |
289 | A | ||
290 | A | D | |
292 | A | ||
293 | A | A | |
294 | A | A | A |
295 | A | A | A |
296 | A | A | A |
297 | A | A | A |
298 | A | A | |
299 | A | D | A |
300 | A | ||
301 | A | A | |
302 | A | A | |
303 | A | A | A |
305 | A | A | A |
306 | A | A | A |
307 | A | A | |
309 | A | A | A |
310 | A | A | A |
311 | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
312 | A | A | A |
313 | A | A | A |
314 | A | A | A |
315 | A | A | A |
316 | A | A | A |
317 | A | A | A |
318 | A | A | A |
319 | A | A | |
320 | A | C | D |
321 | A | A | A |
322 | A | ||
324 | A | ||
325 | A | A | A |
326 | A | A | |
327 | A | A | |
328 | A | A | A |
329 | A | A | |
330 | A | A | A |
332 | A | A | |
333 | A | A | A |
334 | A | A | |
335 | A | D | |
336 | A | C | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
337 | A | A | |
338 | A | A | |
339 | A | A | A |
340 | A | A | |
341 | A | A | A |
342 | A | ||
343 | A | ||
344 | A | A | |
345 | A | ||
346 | A | A | A |
347 | A | ||
348 | A | A | A |
349 | A | A | A |
351 | A | A | A |
352 | A | A | |
353 | A | A | |
355 | A | A | A |
356 | A | ||
357 | A | A | A |
358 | A | A | A |
359 | A | A | A |
360 | A | A | A |
361 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
362 | A | A | A |
363 | A | A | A |
364 | A | A | A |
365 | A | A | A |
366 | A | A | A |
367 | A | A | A |
368 | A | A | |
369 | A | A | A |
370 | A | A | |
371 | A | A | A |
372 | A | A | A |
373 | A | A | A |
374 | A | A | A |
375 | A | A | |
376 | A | C | A |
377 | A | ||
378 | A | ||
379 | A | ||
380 | A | A | A |
381 | A | A | |
382 | A | A | A |
383 | A | A | A |
384 | A | D | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 | |
385 | A | C | ||
386 | A | |||
387 | A | |||
388 | A | A | A | |
389 | A | |||
390 | A | |||
391 | A | |||
392 | A | D | A | |
393 | A | A | A | |
394 | A | A | A | |
395 | A | A | A | |
396 | A | A | A | |
397 | A | A | A | |
398 | A | A | A | |
399 | A | A | A | |
400 | A | A | A | |
401 | A | A | A | |
402 | A | A | A | |
403 | A | A | A | |
404 | A | A | A | |
405 | A | A | A | |
406 | A | A | A | |
407 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
408 | A | A | A |
409 | A | A | A |
410 | A | A | |
411 | A | A | A |
412 | A | A | A |
413 | A | A | A |
414 | A | A | A |
415 | A | A | A |
417 | A | A | A |
419 | A | A | A |
420 | A | A | A |
421 | A | A | A |
422 | A | A | A |
423 | A | A | A |
424 | A | A | B |
425 | A | A | |
426 | A | D | C |
427 | A | A | C |
428 | A | D | A |
429 | A | A | A |
430 | A | A | A |
431 | A | A | A |
432 | A | A | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
433 | A | A | A |
434 | A | A | A |
435 | A | A | A |
436 | A | A | A |
437 | A | A | A |
438 | A | A | A |
439 | A | A | A |
440 | A | A | A |
441 | A | A | A |
442 | A | A | A |
443 | A | A | A |
444 | A | D | A |
445 | A | A | |
446 | A | ||
447 | A | ||
448 | A | A | A |
449 | A | A | A |
450 | A | A | A |
451 | A | A | |
452 | A | ||
453 | A | A | A |
454 | A | A | A |
459 | A |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
460 | A | A | D |
461 | A | D | |
462 | A | D | A |
463 | A | A | A |
465 | A | ||
467 | A | A | A |
469 | A | ||
470 | A | C | A |
471 | A | A | |
472 | A | A | |
473 | A | B | |
474 | A | D | |
475 | A | A | |
478 | A | ||
480 | A | A | |
481 | A | A | A |
482 | A | A | A |
483 | A | A | A |
484 | A | A | A |
486 | A | A | A |
490 | A | C | A |
491 | - | - | - |
492 | - | - | - |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
493 | - | - | - |
494 | - | - | - |
495 | - | - | - |
496 | - | - | - |
表5(续)
序号 | 测试实施例1 | 测试实施例2 | 测试实施例3 |
2-3 | A | A | |
2-5 | A | C | |
2-6 | A | D | |
2-7 | A | ||
2-8 | A | A | |
2-9 | A | ||
2-10 | A | D | A |
2-11 | A | ||
2-12 | A | A | |
2-13 | A | A | |
2-14 | A | C | A |
2-15 | A | A | A |
2-16 | A | ||
2-17 | A | A | |
3-1 | A | A | |
3-2 | A |
Claims (5)
1.一种下述通式(I)的邻苯二酰胺衍生物或其盐,
其中A1代表C1-C8亚烷基,具有至少一个相同或不同的取代基的取代C1-C8亚烷基,所述取代基选自卤原子、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基和C1-C6烷硫基C1-C6烷基和
此外,在所述C1-C8亚烷基和取代C1-C8亚烷基中的任意饱和碳原子可被C2-C5亚烷基取代形成C3-C6环烷基环;在所述C1-C8亚烷基和取代C1-C8亚烷基中的任意两个碳原子可与亚烷基或亚链烯基连接形成C3-C6环烷基环;
R1代表氢原子,巯基,C1-C6烷基,卤代C1-C6烷基,C3-C6链烯基,卤代C3-C6链烯基,C3-C6炔基,卤代C3-C6炔基,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷氧基C1-C6烷基,C1-C6烷硫基C1-C6烷基,单C1-C6烷基氨基C1-C6烷基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基C1-C6烷基,C1-C6烷基羰基,卤代C1-C6烷基羰基,C1-C6烷硫基羰基,C1-C6烷氧基羰基,单C1-C6烷基氨基羰基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基,单C1-C6烷基氨基硫羰基,其中C1-C6烷基是相同或不同的二C1-C6烷基氨基硫羰基,C1-C6烷基羰基C1-C6烷基,C1-C6烷氧基亚氨基C1-C6烷基,C1-C6烷氧基羰基C1-C6烷基,单C1-C6烷基氨基羰基C1-C6烷基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基C1-C6烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯基C1-C6烷基,在其环上具有至少一个相同或不同的取代基的取代苯基C1-C6烷基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯基羰基,具有至少一个相同或不同的取代基的取代苯基羰基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、可以是相同或不同的二C1-C6烷基氨基其中C1-C6烷基和C1-C6烷氧基羰基,苯硫基,具有至少一个相同或不同的取代基的取代苯硫基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基,或具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或
可选择地,R1可以与A1结合形成可以被1或2个相同或不同的氧原子,硫原子或氮原子间隔的5-至8-元环;
R2和R3可以是相同或不同的,代表氢原子、C1-C6烷基;或
可选择地,R2可以与A1或R1结合形成可以被1或2个相同或不同的氧原子,硫原子或氮原子间隔的5-至7-元环;
X可以是相同或不同的,代表卤原子、硝基、C1-C6烷基、卤代C1-C6烷基、C2-C6链烯基、卤代C2-C6链烯基、C2-C6炔基、卤代C2-C6炔基、C3-C6环烷基、卤代C3-C6环烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或卤代C1-C6烷基磺酰基和1代表0至4的整数:和
可选择地,X可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基;和
Y可以是相同或不同的,代表卤原子,C1-C6烷基,卤代C1-C6烷基,羟基卤代C1-C6烷基,C1-C6烷氧基卤代C1-C6烷基,C1-C6烷硫基卤代C1-C6烷基,C3-C6链烯基,卤代C3-C6链烯基,C3-C6炔基,卤代C3-C6炔基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷氧基卤代C1-C6烷氧基,C1-C6烷硫基卤代C1-C6烷氧基,卤代C1-C6烷氧基卤代C1-C6烷氧基,卤代C3-C6链烯氧基,C1-C6烷硫基,卤代C1-C6烷硫基,卤代C1-C6烷氧基卤代C1-C6烷硫基,卤代C1-C6链烯硫基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,单C1-C6烷基氨基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基,C1-C6烷氧基羰基,C3-C6环烷基,卤代C3-C6环烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,苯氧基,具有至少一个相同或不同的取代基的取代苯氧基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,苯硫基,具有至少一个相同或不同的取代基的取代苯硫基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,吡啶氧基,具有至少一个相同或不同的取代基的取代吡啶氧基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,吡啶硫基,具有至少一个相同或不同的取代基的取代吡啶硫基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基和m代表1至5的整数;和
Y可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基;和
n代表0至2的整数。
2.根据权利要求1的邻苯二酰胺衍生物或其盐,其中A1代表C1-C8亚烷基;
R1代表氢原子、C1-C6烷基、卤代C1-C6烷基、C3-C6链烯基、C3-C6炔基、C3-C6环烷基、C1-C6烷硫基、C1-C6烷氧基C1-C6烷基、C1-C6烷硫基C1-C6烷基、C1-C6烷基羰基、单C1-C6烷基氨基羰基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基、单C1-C6烷基氨基硫羰基、其中C1-C6烷基是相同或不同的二C1-C6烷基氨基硫羰基、C1-C6烷基羰基C1-C6烷基、C1-C6烷氧基亚氨基C1-C6烷基、C1-C6烷氧基羰基C1-C6烷基、单C1-C6烷基氨基羰基C1-C6烷基或其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基C1-C6烷基,
R2和R3可以是相同或不同的,代表氢原子或C1-C6烷基;
X可以是相同或不同的,代表卤原子、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或卤代C1-C6烷基磺酰基;和1代表0至4的整数:和
可选择地,X可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基;
Y可以是相同或不同的,代表卤原子,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,卤代C1-C6烷氧基卤代C1-C6烷氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,具有至少一个相同或不同的取代基的取代苯氧基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,或具有至少一个相同或不同的取代基的取代吡啶氧基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基;和m代表1至5的整数;和
Y可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基;和
n代表0至2的整数。
3.一种农业园艺用杀虫剂,其特征在于含有下述通式(I)的邻苯二酰胺衍生物或其盐作为活性成分:
其中A1代表C1-C8亚烷基,具有至少一个相同或不同的取代基的的取代C1-C8亚烷基,所述取代基选自卤原子、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基和C1-C6烷硫基C1-C6烷基和
此外,在所述C1-C8亚烷基和取代C1-C8亚烷基中的任意饱和碳原子可被C2-C5亚烷基取代形成C3-C6环烷基环;在所述C1-C8亚烷基和取代C1-C8亚烷基中的任意两个碳原子可与亚烷基或亚链烯基连接形成C3-C6环烷基环;
R1代表氢原子,巯基,C1-C6烷基,卤代C1-C6烷基,C3-C6链烯基,卤代C3-C6链烯基,C3-C6炔基,卤代C3-C6炔基,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷氧基C1-C6烷基,C1-C6烷硫基C1-C6烷基,单C1-C6烷基氨基C1-C6烷基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基C1-C6烷基,C1-C6烷基羰基,卤代C1-C6烷基羰基,C1-C6烷硫基羰基,C1-C6烷氧基羰基,单C1-C6烷基氨基羰基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基,单C1-C6烷基氨基硫羰基,其中C1-C6烷基是相同或不同的二C1-C6烷基氨基硫羰基,C1-C6烷基羰基C1-C6烷基,C1-C6烷氧基亚氨基C1-C6烷基,C1-C6烷氧基羰基C1-C6烷基,单C1-C6烷基氨基羰基C1-C6烷基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基C1-C6烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯基C1-C6烷基,在其环上具有至少一个相同或不同的取代基的取代苯基C1-C6烷基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯基羰基,具有至少一个相同或不同的取代基的取代苯基羰基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,苯硫基,具有至少一个相同或不同的取代基的取代苯硫基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,杂环基或具有至少一个相同或不同的取代基的取代杂环基,所述取代基选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、单C1-C6烷基氨基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基和C1-C6烷氧基羰基,或
可选择地,R1可以与A1结合形成可以被1或2个相同或不同的氧原子,硫原子或氮原子间隔的5-至8-元环;
R2和R3可以是相同或不同的,代表氢原子、C1-C6烷基;或
可选择地,R2可以与A1或R1结合形成可以被1或2个相同或不同氧原子,硫原子或氮原子间隔的5-至7-元环;
X可以是相同或不同的,代表卤原子、硝基、C1-C6烷基、卤代C1-C6烷基、C2-C6链烯基、卤代C2-C6链烯基、C2-C6炔基、卤代C2-C6炔基、C3-C6环烷基、卤代C3-C6环烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或卤代C1-C6烷基磺酰基和1代表0至4的整数;和
可选择地,X可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基;和
Y可以是相同或不同的,代表卤原子,C1-C6烷基,卤代C1-C6烷基,羟基卤代C1-C6烷基,C1-C6烷氧基卤代C1-C6烷基,C1-C6烷硫基卤代C1-C6烷基,C3-C6链烯基,卤代C3-C6链烯基,C3-C6炔基,卤代C3-C6炔基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷氧基卤代C1-C6烷氧基,C1-C6烷硫基卤代C1-C6烷氧基,卤代C1-C6烷氧基卤代C1-C6烷氧基,卤代C3-C6链烯氧基,C1-C6烷硫基,卤代C1-C6烷硫基,卤代C1-C6烷氧基卤代C1-C6烷硫基,卤代C1-C6链烯硫基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,单C1-C6烷基氨基,其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基,C1-C6烷氧基羰基,C3-C6环烷基,卤代C3-C6环烷基,苯基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,苯氧基,具有至少一个相同或不同的取代基的取代苯氧基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,苯硫基具有至少一个相同或不同的取代基的取代苯硫基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,吡啶氧基,具有至少一个相同或不同的取代基的取代吡啶氧基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,吡啶硫基,具有至少一个相同或不同的取代基的取代吡啶硫基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基;和m代表1至5的整数;和
Y可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基;和
n代表0至2的整数。
4.根据权利要求3的农业园艺用杀虫剂,其中A1代表C1-C8亚烷基;
R1代表氢原子、C1-C6烷基、卤代C1-C6烷基、C3-C6链烯基、C3-C6炔基、C3-C6环烷基、C1-C6烷硫基、C1-C6烷氧基C1-C6烷基、C1-C6烷硫基C1-C6烷基、C1-C6烷基羰基、单C1-C6烷基氨基羰基、其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基、单C1-C6烷基氨基硫羰基、其中C1-C6烷基是相同或不同的二C1-C6烷基氨基硫羰基、C1-C6烷基羰基C1-C6烷基、C1-C6烷氧基亚氨基C1-C6烷基、C1-C6烷氧基羰基C1-C6烷基、单C1-C6烷基氨基羰基C1-C6烷基或其中C1-C6烷基可以是相同或不同的二C1-C6烷基氨基羰基C1-C6烷基;
R2和R3可以是相同或不同的,代表氢原子或C1-C6烷基;
X可以是相同或不同的,代表卤原子、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或卤代C1-C6烷基磺酰基;和1代表0至4的整数:和
可选择地,X可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基;
Y可以是相同或不同的,代表卤原子,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,卤代C1-C6烷氧基卤代C1-C6烷氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,具有至少一个相同或不同的取代基的取代苯基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,具有至少一个相同或不同的取代基的取代苯氧基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基,或具有至少一个相同或不同的取代基的取代吡啶氧基,所述取代基选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基;和m代表1至5的整数;和
Y可与苯环上相邻碳原子连接形成稠合环,所述稠合环可以具有至少一个相同或不同的选自下组的取代基:卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基和卤代C1-C6烷基磺酰基;和
n代表0至2的整数。
5.一种使用农业园艺用杀虫剂的方法,其特征在于为了保护有用作物,使用有效量的根据权利要求3-4任一项的农业园艺用杀虫剂处理目标作物或施用到土壤。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP340379/1998 | 1998-11-30 | ||
JP34037998 | 1998-11-30 | ||
JP23432999 | 1999-08-20 | ||
JP234329/1999 | 1999-08-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1255491A CN1255491A (zh) | 2000-06-07 |
CN1328246C true CN1328246C (zh) | 2007-07-25 |
Family
ID=26531505
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN99122802.2A Expired - Lifetime CN1328246C (zh) | 1998-11-30 | 1999-11-30 | 邻苯二酰胺衍生物或其盐,农业园艺用杀虫剂及其使用方法 |
Country Status (20)
Country | Link |
---|---|
US (1) | US6603044B1 (zh) |
EP (1) | EP1006107B1 (zh) |
KR (1) | KR100404009B1 (zh) |
CN (1) | CN1328246C (zh) |
AR (1) | AR021415A1 (zh) |
AT (1) | ATE479654T1 (zh) |
AU (1) | AU729776B2 (zh) |
BR (1) | BR9905766B1 (zh) |
CO (1) | CO5210941A1 (zh) |
CZ (1) | CZ299375B6 (zh) |
DE (1) | DE69942717D1 (zh) |
DK (1) | DK1006107T3 (zh) |
EG (1) | EG22626A (zh) |
HU (1) | HU229863B1 (zh) |
ID (1) | ID25764A (zh) |
IL (1) | IL133139A (zh) |
PL (1) | PL196644B1 (zh) |
PT (1) | PT1006107E (zh) |
TR (1) | TR199902935A2 (zh) |
TW (1) | TWI225046B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104024222A (zh) * | 2011-11-02 | 2014-09-03 | 日本农药株式会社 | 邻苯二甲酰胺衍生物和含有该衍生物的农业和园艺用杀虫剂及其使用方法 |
Families Citing this family (115)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6747041B1 (en) | 1999-06-24 | 2004-06-08 | Nihon Nohyaku Co., Ltd. | Heterocyclic dicarboxylic acid diamide derivatives, agricultural/horticultural insecticides and method of using the same |
AR030154A1 (es) | 1999-07-05 | 2003-08-13 | Nihon Nohyaku Co Ltd | Derivado de ftalamida, derivado de amina heterociclico util como intermediario para la produccion del mismo, insecticida agrohorticola y metodo para utilizar dicho insecticida |
JP2002105046A (ja) * | 2000-09-25 | 2002-04-10 | Nippon Nohyaku Co Ltd | チオアルキルアミン−s−酸化体及びその塩類 |
DE10115406A1 (de) * | 2001-02-06 | 2002-08-08 | Bayer Ag | Phthalsäurediamide |
ES2245398T3 (es) * | 2001-02-06 | 2006-01-01 | Bayer Cropscience Ag | Diamidas del acido ftalico, un procedimiento para su obtencion y su empleo como agentes pesticidas. |
DK1380209T3 (da) * | 2001-04-17 | 2012-09-24 | Nihon Nohyaku Co Ltd | Sammensætning til et middel til bekæmpelse af skadelige organismer og fremgangsmåde til anvendelse af samme |
KR20040015151A (ko) * | 2001-04-26 | 2004-02-18 | 니혼노야쿠가부시키가이샤 | 프탈아미드 유도체, 농원예용 살충제 및 그의 사용 방법 |
US20040097595A1 (en) * | 2001-04-26 | 2004-05-20 | Hayami Nakao | Phthalamide derivatives, insecticides for agricultural and horticultural use and method for application thereof |
AR035884A1 (es) | 2001-05-18 | 2004-07-21 | Nihon Nohyaku Co Ltd | Derivado de amida aromatico sustituido, derivado de amina aromatico sustituido con un grupo fluoroalquilo util como intermediario para obtener el mismo, insecticida para agrohorticultura que lo contiene y metodo para usar este ultimo |
AU2002323743A1 (en) * | 2001-08-01 | 2003-02-17 | Nissan Chemical Industries, Ltd. | Substituted amides and pest controllers |
DE10157545A1 (de) * | 2001-11-23 | 2003-06-12 | Bayer Cropscience Gmbh | Herbizide Mittel enthaltend Benzoylpyrazole und Safener |
CN100354260C (zh) | 2002-05-02 | 2007-12-12 | 拜尔农作物科学股份公司 | 邻苯二酰胺衍生物、农业或园艺业杀虫剂及其使用方法 |
JP2004018506A (ja) * | 2002-06-20 | 2004-01-22 | Bayer Ag | 殺虫性フタラミド誘導体 |
WO2004018410A1 (ja) * | 2002-08-26 | 2004-03-04 | Nissan Chemical Industries, Ltd. | 置換ベンズアニリド化合物及び有害生物防除剤 |
JP4411582B2 (ja) * | 2002-08-26 | 2010-02-10 | 日本農薬株式会社 | スルホンアミド誘導体及び農園芸用殺虫剤並びにその使用方法 |
DE10248257A1 (de) * | 2002-10-16 | 2004-04-29 | Bayer Cropscience Ag | Wirkstoffkombinationen im insektiziden und akariziden Eigenschaften |
DE10310906A1 (de) * | 2003-03-13 | 2004-09-23 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
JP2004277333A (ja) | 2003-03-14 | 2004-10-07 | Bayer Cropscience Ag | 殺虫性フタラミド誘導体 |
DE10330723A1 (de) * | 2003-07-08 | 2005-02-03 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10330724A1 (de) | 2003-07-08 | 2005-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
WO2005022167A2 (en) * | 2003-08-29 | 2005-03-10 | The University Of North Carolina At Greensboro | Compounds that act to modulate insect growth and methods and systems for identifying such compounds |
US8637237B2 (en) * | 2003-08-29 | 2014-01-28 | The University Of North Carolina At Greensboro | Methods, compositions, and systems for the identification of species-specific or developmental stage-specific insecticides |
US20100240056A1 (en) * | 2003-08-29 | 2010-09-23 | Henrich Iii Vincent C | Methods And Systems For Screening Species-Specific Insecticidal Candidates |
CA2537124C (en) * | 2003-08-29 | 2012-08-07 | Mitsui Chemicals, Inc. | Agricultural/horticultural insecticide and method for using the same |
JP2005114718A (ja) * | 2003-10-10 | 2005-04-28 | Bayer Cropscience Ag | 殺虫剤活性化合物を特定するための方法 |
JP2006076990A (ja) * | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
US7459562B2 (en) * | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
TW200538453A (en) * | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
US7432373B2 (en) * | 2004-06-28 | 2008-10-07 | Bristol-Meyers Squibb Company | Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors |
US7439246B2 (en) * | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
US7173031B2 (en) | 2004-06-28 | 2007-02-06 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
DE102004035134A1 (de) | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von Halogenalkylnicotinsäurederivaten, Anthranilsäureamiden oder Phthalsäurediamiden und Safenern |
GB0418047D0 (en) | 2004-08-12 | 2004-09-15 | Syngenta Participations Ag | Fungicidal compositions |
WO2006022225A1 (ja) * | 2004-08-23 | 2006-03-02 | Nihon Nohyaku Co., Ltd. | 光学活性フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法 |
WO2006024412A2 (en) * | 2004-08-31 | 2006-03-09 | Bayer Cropscience Ag | Optically active phthalamides |
CA2577942A1 (en) * | 2004-08-31 | 2006-03-09 | Bayer Cropscience Ag | Chiral 3-halophthalic acid derivatives |
GB0419420D0 (en) * | 2004-09-01 | 2004-10-06 | Syngenta Participations Ag | Novel insecticides |
TW200626532A (en) | 2004-09-21 | 2006-08-01 | Syngenta Participations Ag | Novel insecticides |
GB0422401D0 (en) | 2004-10-08 | 2004-11-10 | Syngenta Participations Ag | Fungicidal compositions |
DE102004055582A1 (de) | 2004-11-18 | 2006-05-24 | Bayer Cropscience Ag | N-Heterocyclyl-phthalsäurediamide |
EP1688039A3 (en) * | 2005-02-08 | 2006-10-11 | Nihon Nohyaku Co., Ltd. | Agricultural and horticultural poison bait preparation |
JP2006347936A (ja) | 2005-06-15 | 2006-12-28 | Bayer Cropscience Ag | 殺虫性ベンズアニリド類 |
DE102005059467A1 (de) * | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
DE102005059466A1 (de) * | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
BRPI0619980A2 (pt) * | 2005-12-15 | 2014-10-14 | Nihon Nohyaku Co Ltd | Derivados de ftalamida e de anilina, inseticida agrícola ou hortícula, e, método de uso do mesmo |
TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
TWI324908B (en) * | 2006-01-05 | 2010-05-21 | Du Pont | Liquid formulations of carboxamide arthropodicides |
UA95091C2 (ru) * | 2006-01-05 | 2011-07-11 | Э.И. Дю Пон Де Немур Энд Компани | Артроподицидная суспензионная концентрированная композиция и способ борьбы с членистоногим вредителем |
US7807714B2 (en) | 2006-02-09 | 2010-10-05 | Syngenta Crop Protection, Inc. | Fungicidal compositions |
DE102006010201A1 (de) * | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Synergistische Zusammensetzungen |
DE102006010208A1 (de) * | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006010205A1 (de) * | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006010206A1 (de) * | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006015197A1 (de) * | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Wirkstoffkombination mit insektiziden Eigenschaften |
DE102006010204A1 (de) * | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006037120A1 (de) * | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
DE102006010211A1 (de) * | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006010209A1 (de) * | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
US8198216B2 (en) * | 2006-03-27 | 2012-06-12 | Syngenta Crop Protection Llc | Granular formulation |
WO2007112844A1 (de) * | 2006-03-29 | 2007-10-11 | Bayer Cropscience Ag | Neue kristalline modifikationen von 3-chlor-n2-[(1s)-1-methyl-2-(methyl-sulfonyl)ethyl]-n1- {2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)- ethyl]phenyl}phthalamid |
EP2001300A2 (en) * | 2006-03-31 | 2008-12-17 | E.I. Du Pont De Nemours And Company | Method for disrupting reproductive performance of arthropods |
DK2016067T3 (da) * | 2006-04-28 | 2012-10-22 | Syngenta Participations Ag | Insecticidforbindelser |
DE102006027732A1 (de) * | 2006-06-16 | 2008-01-10 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006027731A1 (de) | 2006-06-16 | 2007-12-20 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
WO2008021152A2 (en) * | 2006-08-09 | 2008-02-21 | E. I. Du Pont De Nemours And Company | Agronomic method |
WO2008037376A2 (de) * | 2006-09-30 | 2008-04-03 | Bayer Cropscience Aktiengesellschaft | Verbesserung der biologischen wirkung von agrochemischen zusammensetzungen bei applikation in das kultursubstrat, geeignete formulierungen und ihre anwendung |
KR20090060446A (ko) * | 2006-09-30 | 2009-06-12 | 바이엘 크롭사이언스 아게 | 재배 기재에 적용시 농약 조성물의 생물학적 작용 개선, 적합한 제제 및 그의 용도 |
WO2008037378A2 (de) * | 2006-09-30 | 2008-04-03 | Bayer Cropscience Aktiengesellschaft | Suspensionskonzentrate zur verbesserung der wurzelaufnahme von agrochemischen wirkstoffen |
TWI484910B (zh) * | 2006-12-01 | 2015-05-21 | Du Pont | 甲醯胺殺節肢動物劑之液體調配物 |
CL2007003748A1 (es) * | 2006-12-22 | 2008-07-18 | Bayer Cropscience Ag | Composicion pesticida que comprende fosetil-al, propamocarb-hcl y una sustancia insecticida activa; y metodo para controlar hongos fitopatogenos o insecticidas daninos de las plantas, cultivos o semillas que comprende aplicar dicha composicion. |
TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
WO2009002810A1 (en) * | 2007-06-27 | 2008-12-31 | E. I. Du Pont De Nemours And Company | Solid formulations of carboxamide arthropodicides |
CA2685081A1 (en) * | 2007-06-27 | 2008-12-31 | E.I. Du Pont De Nemours And Company | Solid formulations of carboxamide arthropodicides |
CN103416421B (zh) * | 2007-07-27 | 2016-07-27 | 拜尔农作物科学股份公司 | 三元活性化合物结合物 |
EP2033516A1 (de) * | 2007-09-05 | 2009-03-11 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
EP2070414A1 (en) * | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Active compound combinations |
TWI468407B (zh) | 2008-02-06 | 2015-01-11 | Du Pont | 中離子農藥 |
EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
US8642805B2 (en) | 2008-07-29 | 2014-02-04 | Iharanikkei Chemical Industry Co., Ltd. | Method of producing phthaloyl dichloride compound, catalyst for use in the method, and method of forming the catalyst |
EP2227951A1 (de) | 2009-01-23 | 2010-09-15 | Bayer CropScience AG | Verwendung von Enaminocarbonylverbindungen zur Bekämpfung von durch Insekten übertragenen Viren |
JP2011042643A (ja) * | 2009-07-24 | 2011-03-03 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
EP2461684A2 (en) | 2009-08-05 | 2012-06-13 | E. I. du Pont de Nemours and Company | Mesoionic pesticides |
AU2010279587A1 (en) | 2009-08-05 | 2012-02-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
US20120309812A1 (en) * | 2010-02-03 | 2012-12-06 | Syngenta Crop Protection Llc | Insecticidal compounds |
EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
CN101803598B (zh) * | 2010-04-30 | 2013-05-29 | 江苏龙灯化学有限公司 | 低浓度氟虫双酰胺悬浮剂 |
MY156670A (en) | 2010-05-27 | 2016-03-15 | Du Pont | Crystalline form of 4-[5-[3-chloro-5-(trifluoromethly)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-n-[2-oxo-2-[(2,2,2-trifluoroethyl) amino]ethyl]-1-naphthalenecarboxamide |
CN101836643B (zh) * | 2010-06-01 | 2012-12-12 | 扬州大学 | 防治小菜蛾等蔬菜害虫的农药制剂 |
CN101948413B (zh) * | 2010-08-31 | 2013-03-27 | 上海赫腾精细化工有限公司 | 氟虫酰胺的制备方法 |
US9433212B2 (en) | 2011-06-06 | 2016-09-06 | Nihon Nohyaku Co., Ltd. | Plant growth regulator and method for using the same |
CN102503876A (zh) * | 2011-09-28 | 2012-06-20 | 南开大学 | 双酰胺衍生物及其制备和应用 |
CN102396477A (zh) * | 2011-12-14 | 2012-04-04 | 湖南化工研究院 | 仲丁威与氟虫双酰胺的杀虫组合物 |
CN102578117A (zh) * | 2012-01-19 | 2012-07-18 | 华南理工大学 | 氟虫双酰胺与鱼藤酮复配悬浮剂及其制备方法 |
CN103300000B (zh) * | 2012-03-12 | 2016-04-06 | 陕西韦尔奇作物保护有限公司 | 一种含环虫酰肼与酰胺类的杀虫组合物 |
RU2015111260A (ru) | 2012-08-30 | 2016-10-20 | Пайонир Хай-Бред Интернэшнл, Инк. | Способы покрытия семян с применением композиции на основе агониста рецептора рианодина |
CN103503896A (zh) * | 2012-12-05 | 2014-01-15 | 江苏辉丰农化股份有限公司 | 具有增效作用的杀虫组合物 |
KR20160002926A (ko) | 2013-04-19 | 2016-01-08 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 살충성을 가지는 활성 화합물의 배합물 |
CN104106592A (zh) * | 2013-04-22 | 2014-10-22 | 陕西美邦农药有限公司 | 一种含氟苯虫酰胺与拟除虫菊酯类的杀虫组合物 |
CN103420884B (zh) * | 2013-05-17 | 2015-12-02 | 南开大学 | 具有光学活性和几何异构的双酰胺衍生物与制备及应用 |
CN103392705A (zh) * | 2013-07-22 | 2013-11-20 | 浙江威尔达化工有限公司 | 一种含氟苯虫酰胺和烯啶虫胺的杀虫组合物及其应用 |
CN103461376B (zh) * | 2013-09-05 | 2015-08-12 | 江苏龙灯化学有限公司 | 一种含氟虫双酰胺和哒嗪硫磷的农药杀虫组合物 |
CN104855399B (zh) * | 2015-05-02 | 2018-06-19 | 广东中迅农科股份有限公司 | 一种含有丁烯氟虫腈和氟苯虫酰胺的杀虫组合物 |
JP6464428B2 (ja) * | 2015-08-31 | 2019-02-06 | 株式会社ダイセル | 増粘安定剤、及びそれを用いた増粘安定化組成物 |
WO2017174430A1 (en) | 2016-04-06 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Combination of nuclear polyhedrosis virus and diamides |
US20190387661A1 (en) | 2016-12-08 | 2019-12-26 | Bayer Cropscience Aktiengesellschaft | Use of insecticides for controlling wireworms |
CN109574892B (zh) * | 2018-11-29 | 2020-11-17 | 常州沃腾化工科技有限公司 | 微通道反应制备3-碘-n-(1,1-二甲基-2-甲硫基乙基)邻氨甲酰苯甲酸的方法 |
CN109485588A (zh) * | 2018-12-25 | 2019-03-19 | 成都蓝蜻蜓生物技术有限公司 | 一种氟虫双酰胺的合成方法 |
CN110272361B (zh) * | 2019-07-11 | 2021-06-11 | 华东理工大学 | 含烷氧基六氟异丙基的邻苯二甲酰胺类化合物及其应用 |
WO2022200364A1 (en) | 2021-03-25 | 2022-09-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
BR112023023856A2 (pt) | 2021-05-14 | 2024-01-30 | Syngenta Crop Protection Ag | Controle de pragas de insetos, ácaros e nematódeos |
MX2023015268A (es) | 2021-06-24 | 2024-01-19 | Pi Industries Ltd | Una combinacion de flubendiamida y extracto de algas. |
WO2022268813A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022268815A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2023105065A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2023105064A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61180753A (ja) * | 1985-02-06 | 1986-08-13 | Nippon Kayaku Co Ltd | フタラミン酸誘導体およびそれを有効成分とする除草剤又は植物生長調節剤 |
EP0325983A2 (de) * | 1988-01-26 | 1989-08-02 | Hoechst Aktiengesellschaft | N-Phenylbenzamide und N-Phenylbenzamidoxime, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE119428C (zh) | ||||
DE3305569A1 (de) | 1983-02-18 | 1984-08-23 | Bayer Ag, 5090 Leverkusen | Biscarboxamide zur bekaempfung von erkrankungen sowie verfahren zu ihrer herstellung |
US4937253A (en) | 1985-04-19 | 1990-06-26 | Smithkline Beecham Corporation | Ester prodrugs |
JPH07107601B2 (ja) | 1985-07-26 | 1995-11-15 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
FR2655339B2 (fr) | 1989-04-19 | 1992-04-10 | Medgenix Group Sa | Composes et complexes utiles notamment en imagerie medicale. |
IL95157A (en) | 1989-07-28 | 1996-05-14 | Rohm & Haas | S-Melted Beta-Thioacrylamides, their preparation and use as bactericides |
-
1999
- 1999-11-19 CZ CZ0409999A patent/CZ299375B6/cs not_active IP Right Cessation
- 1999-11-23 TW TW088120428A patent/TWI225046B/zh not_active IP Right Cessation
- 1999-11-24 DE DE69942717T patent/DE69942717D1/de not_active Expired - Lifetime
- 1999-11-24 AT AT99123195T patent/ATE479654T1/de active
- 1999-11-24 DK DK99123195.2T patent/DK1006107T3/da active
- 1999-11-24 PT PT99123195T patent/PT1006107E/pt unknown
- 1999-11-24 EP EP99123195A patent/EP1006107B1/en not_active Expired - Lifetime
- 1999-11-25 IL IL13313999A patent/IL133139A/en not_active IP Right Cessation
- 1999-11-26 AR ARP990106038A patent/AR021415A1/es active IP Right Grant
- 1999-11-29 CO CO99074853A patent/CO5210941A1/es not_active Application Discontinuation
- 1999-11-29 KR KR10-1999-0053476A patent/KR100404009B1/ko active IP Right Grant
- 1999-11-29 US US09/449,420 patent/US6603044B1/en not_active Expired - Lifetime
- 1999-11-29 ID IDP991101D patent/ID25764A/id unknown
- 1999-11-30 HU HU9904444A patent/HU229863B1/hu unknown
- 1999-11-30 TR TR1999/02935A patent/TR199902935A2/xx unknown
- 1999-11-30 BR BRPI9905766-2A patent/BR9905766B1/pt not_active IP Right Cessation
- 1999-11-30 CN CN99122802.2A patent/CN1328246C/zh not_active Expired - Lifetime
- 1999-11-30 EG EG152699A patent/EG22626A/xx active
- 1999-11-30 AU AU61790/99A patent/AU729776B2/en not_active Expired
- 1999-11-30 PL PL336866A patent/PL196644B1/pl unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61180753A (ja) * | 1985-02-06 | 1986-08-13 | Nippon Kayaku Co Ltd | フタラミン酸誘導体およびそれを有効成分とする除草剤又は植物生長調節剤 |
EP0325983A2 (de) * | 1988-01-26 | 1989-08-02 | Hoechst Aktiengesellschaft | N-Phenylbenzamide und N-Phenylbenzamidoxime, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104024222A (zh) * | 2011-11-02 | 2014-09-03 | 日本农药株式会社 | 邻苯二甲酰胺衍生物和含有该衍生物的农业和园艺用杀虫剂及其使用方法 |
Also Published As
Publication number | Publication date |
---|---|
KR100404009B1 (ko) | 2003-11-03 |
CZ409999A3 (cs) | 2000-06-14 |
HU9904444D0 (en) | 2000-02-28 |
AU6179099A (en) | 2000-06-01 |
EP1006107A3 (en) | 2003-02-05 |
HUP9904444A3 (en) | 2003-06-30 |
DK1006107T3 (da) | 2010-11-15 |
HUP9904444A2 (hu) | 2001-11-28 |
PT1006107E (pt) | 2010-10-04 |
BR9905766B1 (pt) | 2010-11-30 |
IL133139A (en) | 2004-08-31 |
TR199902935A3 (tr) | 2000-06-21 |
EP1006107A2 (en) | 2000-06-07 |
EG22626A (en) | 2003-05-31 |
PL336866A1 (en) | 2000-06-05 |
CN1255491A (zh) | 2000-06-07 |
US6603044B1 (en) | 2003-08-05 |
HU229863B1 (en) | 2014-10-28 |
CO5210941A1 (es) | 2002-10-30 |
IL133139A0 (en) | 2001-03-19 |
ATE479654T1 (de) | 2010-09-15 |
ID25764A (id) | 2000-11-02 |
AU729776B2 (en) | 2001-02-08 |
PL196644B1 (pl) | 2008-01-31 |
EP1006107B1 (en) | 2010-09-01 |
TWI225046B (en) | 2004-12-11 |
AR021415A1 (es) | 2002-07-17 |
KR20000035763A (ko) | 2000-06-26 |
BR9905766A (pt) | 2001-07-03 |
DE69942717D1 (de) | 2010-10-14 |
TR199902935A2 (xx) | 2000-06-21 |
CZ299375B6 (cs) | 2008-07-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1328246C (zh) | 邻苯二酰胺衍生物或其盐,农业园艺用杀虫剂及其使用方法 | |
KR100582492B1 (ko) | 프탈산디아미드유도체,농원예용살충제및살충제의사용방법 | |
EP1445251B1 (en) | Aminoacetonitrile derivative, agricultural and horticultural insecticide containing the same, and use thereof | |
CN100358863C (zh) | 芳族二酰胺衍生物或其盐、农艺组合物及其使用方法 | |
KR100429276B1 (ko) | 프탈아미드 유도체, 그의 제조 중간체, 및 농업/원예용살충제 및 이의 사용 방법 | |
EP1188745B1 (en) | Heterocyclic dicarboxylic acid diamide derivatives, agricultural/horticultural insecticides and method of using the same | |
CN100443467C (zh) | 取代的芳族酰胺衍生物、它们的中间体、含有它们的农艺杀虫剂和它们的使用方法 | |
US20010041814A1 (en) | Phthalic acid diamide derivatives fluorine-containing aniline compounds as starting material, agricultural and horticultural insecticides, and a method for application of the insecticides | |
EP1195375B1 (en) | Benzamide derivatives, insecticides for agricultural and horticultural use and usage thereof | |
JP4411582B2 (ja) | スルホンアミド誘導体及び農園芸用殺虫剤並びにその使用方法 | |
JP4573075B2 (ja) | フタル酸ジアミド誘導体及び農園芸用殺虫剤並びにその使用方法 | |
ES2350814T3 (es) | Derivado de ftalimida o sus sales insecticida agrohortícola y método para la utilización del mismo. |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
PB01 | Publication | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CX01 | Expiry of patent term | ||
CX01 | Expiry of patent term |
Granted publication date: 20070725 |