CN1237972A - 8-氮杂二环[3.2.1]辛烷-,8-氮杂二环[3.2.1]辛-6-烯,9-氮杂二环[3.3.1]壬烷-,9-氮杂-3-氧杂二环[3.3.1]壬烷-,9-氮杂-3-硫杂二环[3,3,1]壬烷衍生物,其制备方法及其作为杀虫剂的用途 - Google Patents
8-氮杂二环[3.2.1]辛烷-,8-氮杂二环[3.2.1]辛-6-烯,9-氮杂二环[3.3.1]壬烷-,9-氮杂-3-氧杂二环[3.3.1]壬烷-,9-氮杂-3-硫杂二环[3,3,1]壬烷衍生物,其制备方法及其作为杀虫剂的用途 Download PDFInfo
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- CN1237972A CN1237972A CN97199712A CN97199712A CN1237972A CN 1237972 A CN1237972 A CN 1237972A CN 97199712 A CN97199712 A CN 97199712A CN 97199712 A CN97199712 A CN 97199712A CN 1237972 A CN1237972 A CN 1237972A
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- halogen
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- DVVZRIIREIUXSR-UHFFFAOYSA-N 3-oxa-9-azabicyclo[3.3.1]nonane Chemical compound C1OCC2CCCC1N2 DVVZRIIREIUXSR-UHFFFAOYSA-N 0.000 title 1
- PQXJUNOBLADZSB-UHFFFAOYSA-N 3-thia-9-azabicyclo[3.3.1]nonane Chemical class C1SCC2CCCC1N2 PQXJUNOBLADZSB-UHFFFAOYSA-N 0.000 title 1
- RSZKGHOJCWQNKU-UHFFFAOYSA-N 8-azabicyclo[3.2.1]oct-6-ene Chemical compound C1CCC2C=CC1N2 RSZKGHOJCWQNKU-UHFFFAOYSA-N 0.000 title 1
- DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical compound C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 title 1
- ATPGYYPVVKZFGR-UHFFFAOYSA-N 9-azabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1N2 ATPGYYPVVKZFGR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 239000000203 mixture Substances 0.000 claims abstract description 63
- -1 cyano, hydroxy Chemical group 0.000 claims abstract description 42
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 32
- 150000002367 halogens Chemical class 0.000 claims abstract description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 29
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 9
- 239000001301 oxygen Chemical group 0.000 claims abstract description 9
- 229910052760 oxygen Chemical group 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 7
- 150000001408 amides Chemical class 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000004429 atom Chemical group 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims abstract description 3
- 230000001069 nematicidal effect Effects 0.000 claims abstract description 3
- 241000238631 Hexapoda Species 0.000 claims description 32
- 239000002585 base Substances 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 230000002829 reductive effect Effects 0.000 claims description 10
- 125000001118 alkylidene group Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 241000244206 Nematoda Species 0.000 claims description 5
- 239000005864 Sulphur Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 4
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical group C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims description 2
- 230000002939 deleterious effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000005645 nematicide Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- 239000003085 diluting agent Substances 0.000 abstract description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000004450 alkenylene group Chemical group 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical group S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 abstract 1
- 125000005275 alkylenearyl group Chemical group 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 238000009834 vaporization Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000013375 chromatographic separation Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 229920001983 poloxamer Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000004546 suspension concentrate Substances 0.000 description 6
- QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003094 microcapsule Substances 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
- 239000008267 milk Substances 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 4
- 239000005660 Abamectin Substances 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
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- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 3
- 241001556089 Nilaparvata lugens Species 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 3
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
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- 239000007859 condensation product Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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- ZRKSVHFXTRFQFL-UHFFFAOYSA-N isocyanomethane Chemical compound C[N+]#[C-] ZRKSVHFXTRFQFL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229940031815 mycocide Drugs 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
Abstract
式(Ⅰ)化合物:P-R2-Q,或其衍生的酸加成盐,季铵盐或N-氧化物,其中每个P和Q各自独立地为式(B)的基团,其中J为式-CH2-X-CH2-(其中X为亚甲基,硫或氧),X’C=CY或X’WC-CYZ(其中X’,W,Y和Z各自独立地为氢,羟基,酰氧基,烷氧基,烷基甲硅烷氧基或卤素)的二合基团;R1为可选择取代的苯基或,含有1至3个各自选自氮,氧和硫原子的杂原子的5-或6-元杂环系统,且在环中相邻原子间至少存在一个不饱和基团(双键),所述杂环可选择地被苯环稠合,其中如果存在取代基,取代基选自卤原子,氰基,烷基,链烯基,链炔基,烷氧基,卤代烷基,卤代链烯基,烷硫基和烷基氨基,上述基团至多含有六碳原子;R2为二合链基并为取代或未取代的亚烷基,亚烷芳基,亚烷杂芳基,亚链烯基,亚烷基芳基亚烷基,羰基或二酰基,条件是R2为亚链烯基或亚烷基芳基亚烷基时,所述基团不具有直接键连在式(B)环氮原子上的不饱和碳原子;R3是氢,氰基,羟基,烷基,烷氧基,氨基,硝基,异氰酸基,酰氨基,羟基烷基,可选择取代的杂芳基,烷氧基烷基,卤代烷基,卤代羟基烷基,芳烷氧基烷基,乙酰氧基烷基,偕胺肟基,磺酰基氧烷基,氨基烷基,烷氧基羰基氨基,酰氨基烷基,氰烷基,亚氨基,甲酰基,酰基或其羧酸或酯或酰胺,或链烯基或链炔基,所述链烯基或链炔基各自可被卤素,烷氧基,环烷基,可选择取代的芳基,可选择取代的杂芳基或氰基可选择地取代;含有式(Ⅰ)化合物和适合载体或稀释剂的杀虫,杀螨或杀线虫组合物;在生长地消灭和防治有害昆虫,螨或线虫的方法,其中包含用有效量的式(Ⅰ)化合物或上述组合物处理害虫或害虫生长地。
Description
本发明涉及新的二环胺衍生物,其制备方法,含有其的杀虫组合物,以及使用其消灭和防治有害昆虫的方法。
式(Ⅰ)化合物,或其衍生的酸加成盐,季铵盐或N-氧化物
P-R2-Q (Ⅰ)
其中每个P和Q各自独立地为式(B)的基团:
其中J为式-CH2-X-CH2-(其中X为亚甲基,硫或氧),X’C=CY或X’WC-CYZ(其中X’,W,Y和Z各自独立地为氢,羟基,乙酰氧基,烷氧基,烷基甲硅烷氧基或卤素)的二合基团;R1为可选择取代的苯基或,含有1至3个各自选自氮,氧和硫原子的杂原子的5-或6-元杂环系统,且在环中相邻原子间至少存在一个不饱和基团(双键),所述杂环可选择地被苯环稠合,其中如果存在取代基,取代基选自卤原子,氰基,烷基,链烯基,链炔基,烷氧基,卤代烷基,卤代链烯基,烷硫基和烷基氨基,上述基团至多含有六碳原子;R2为二合链基并为取代或未取代的亚烷基,亚烷芳基,亚烷杂芳基,亚链烯基,亚烷基芳基亚烷基,羰基或二酰基,条件是R2为亚链烯基或亚烷基芳基亚烷基时所述基团不具有直接键连在式(B)环氮原子上的不饱和碳原子;R3是氢,氰基,羟基,烷基,烷氧基,氨基,硝基,异氰酸基,酰氨基,羟基烷基,可选择取代的杂芳基,烷氧基烷基,卤代烷基,卤代羟基烷基,芳烷氧基烷基,酰氧基烷基,偕胺肟基,磺酰基氧烷基,氨基烷基,烷氧基羰基氨基,乙酰氨基烷基,氰烷基,亚氨基,甲酰基,酰基或其羧酸或酯或酰胺,或链烯基或链炔基,所述链烯基或链炔基各自可被卤素,烷氧基,环烷基,可选择取代的芳基,可选择取代杂芳基或氰基可选择地取代。
应理解到的是,由于R1和R3基团存在外或内的相对位置,式(Ⅰ)的二环胺化合物存在一或多个异构体形式,且本发明包括各种外和内形式及其各种比例的混合物,以及由顺和反取代方式或存在R1,R2或R3的手性中心引起的异构变体。
R1表示的5-和6-元环系统的实例包括基于吡啶,吡嗪,哒嗪,嘧啶,吡咯,吡唑,咪唑,1,2,3-和1,2,4-三唑,呋喃,噻吩,噁唑,并噁唑,噻唑,异噻唑,1,2,3-和1,3,4-噁二唑,和1,2,3-和1,3,4-噻二唑的基团,及其含有一个双键的部分还原形式,以及基于氧杂硫杂环戊二烯,间二氧杂环戊烯,和含有一个双键的二硫杂环戊二烯环的基团。优选的R1代表卤素取代的苯基,吡啶基或二嗪基。
当R1是与苯环稠合的5-或6-元杂环时,其优选为苯并噁唑,吲哚,苯并呋喃,苯并噻吩或苯并咪唑。
卤素包括氟,氯,溴和碘。
烷基部分优选包含1至6,更优选1-4个碳原子。它们可为直链或支链形式,例如甲基,乙基,正-或异丙基,或正-,仲-,异-或叔-丁基。
卤代烷基优选为C1-6卤代烷基,特别是氟烷基(例如三氟甲基,2,2,2-三氟乙基或2,2-二氟乙基)或氯代烷基。
链烯基和链炔基取代基优选包含2至6,更优选2至4个碳原子。它们可为直链或支链形式,且如果适合链烯基部分可为(E)-或(Z)-构型。其实例为乙烯基,烯丙基和炔丙基。
芳基包括萘基但优选苯基。
杂芳基包括含有一,二,三或四个选自氧,硫和氮的杂原子的5-和6-元芳环且其可被苯环系统稠和。杂芳基的实例为吡啶基,嘧啶基,哒嗪基,吡嗪基,三嗪基(1,2,3-,1,2,4-和1,3,5-),呋喃基,噻吩基,吡咯基,吡唑基,咪唑基,三唑基(1,2,3-和1,2,4-),四唑基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,喹啉基,异喹啉基,噌啉基,喹唑啉基,喹喔啉基,吲哚基,异吲哚基,苯并呋喃基,苯并噻吩基和苯并咪唑啉基。
亚烷二氧基是一个环取代基,且特别是C1-4亚烷二氧基。亚烷二氧基可选择地被卤素取代(特别是氟),例如为亚甲二氧基(OCH2O)或二氟亚甲基二氧基(OCF2O)。
适合的酸加成盐包括的酸为无机酸如盐酸,氢溴酸,硫酸,硝酸和磷酸,或有机羧酸如草酸,酒石酸,乳酸,丁酸,苯甲酸,己酸和邻苯二甲酸,或磺酸如甲烷、苯和甲苯磺酸,其它有机羧酸的实例包括卤代羧酸如三氟乙酸。
本发明的一个方面是提供了式(Ⅰ)化合物,或其衍生的酸加成盐,季铵盐或N-氧化物,其中J为式-CH2-X-CH2-的二合基团(其中X为亚甲基,硫或氧),X’C=CY或X’WC-CYZ(其中X’,W,Y和Z各自独立地为氢,羟基,酰氧基(特别是C1-4烷基羰基),烷氧基(特别是C1-4烷氧基),烷基甲硅烷氧基(特别是C1-4甲硅烷氧基)或卤素);R1为可选择取代的苯基或含有1至3个各自选自氮,氧和硫原子的杂原子的5-或6-元杂环系统,且在环中相邻原子间至少存在一个不饱和基团(双键),所述杂环可选择地被苯环稠和,其中如果存在取代基,取代基选自卤原子,烷基(特别是C1-4烷基),链烯基(特别是C2-4链烯基),链炔基(特别是C2-4链炔基),烷氧基(特别是C1-4烷氧基),卤代烷基(特别是C1-4卤代烷基),卤代链烯基(特别是C2-4卤代链烯基),烷硫基(特别是C1-4烷硫基),和烷基氨基(特别是单-或二-(C1-4烷基)氨基,如单-或二-(C1-3烷基)氨基);R2为二价的连接基并为取代或未被取代的亚烷基(如被卤素,C1-4烷基或羟基可选择取代的C1-8亚烷基),亚烷基芳基(如被卤素,C1-4烷基或羟基可选择取代的C1-6亚烷基苯基),亚烷基杂芳基(如被卤素,C1- 4烷基或羟基可选择取代的C1-6亚烷基杂芳基;其中杂芳基特别为吡啶基,嘧啶基或1,2,4-噻唑基),亚链烯基(特别是被卤素或C1-4烷基可选择取代的C4-6链烯基),亚烷基芳基亚烷基(特别是被卤素或C1-4烷基可选择取代的C3-6亚烷基苯基(C3-6)亚烷基),羰基或二乙酰基(如C(O)R4C(O)其中R4为(CH2)n或苯环(被卤素,C1-4烷基,C1-4卤代烷基,C1-4烷氧基或C1-4卤代烷氧基可选择地取代)和n为0或1-6的整数),条件是当R2为亚链烯基或亚烷基芳基亚烷基时,所述基团不具有直接键连在式(B)环氮原子上的不饱和碳原子,且当所述基团被卤素或羟基取代时,所述取代基不直接键连在式(B)环氮原子上;R3为氰基,羟基,烷基(特别是C1-4烷基),烷氧基(特别是C1-4烷氧基),氨基(特别是未被取代的,单-或二-(C1-4)烷基氨基或被甲酰基取代的氨基),硝基,异氰酸基,乙酰氨基(特别是C1-4烷基羰基氨基或苯基羰基氨基),羟基烷基(特别是单羟基(C1-4)烷基),可选择取代的杂芳基(特别是被卤素,C1-4烷基,C1-4卤代烷基,C1-4烷氧基或C1-4卤代烷氧基可选择取代的四唑基,噁二唑基,吡啶基或嘧啶基),烷氧基烷基(特别是C1-4烷氧基(C1-4)烷基),卤代烷基(特别是C1-4卤代烷基),卤代羟烷基(特别是C1-4卤代羟基烷基,如2-羟基-1,1-二氟乙基),芳烷氧基烷基(特别是苯基(C1-4)烷氧基(C1-4)烷基),乙酰氧烷基(特别是C1-4烷基羰氧基(C1-4)烷基),酰胺肟基(C(NH2)NOH),磺酰氧基烷基(特别是磺酰氧基(C1-4)烷基),氨基烷基(特别是氨基(C1-4)烷基),烷氧基羰基氨基(特别是(C1-4)烷氧基羰基氨基),乙酰氨基烷基(特别是C1-4烷基羰基氨基(C1-4)烷基或苯基羰基氨基(C1-4)烷基),氰基氨基(C1-4氰基烷基),亚氨基(特别是氰基亚氨基(HON=CH)或C1-4烷氧基亚氨基),甲酰基,乙酰基(特别是C1-4烷基羰基)或其羧酸或酯(特别是C1-4烷基酯)或酰胺(特别是未取代的或N,N-二(C1-4)烷基酰胺),或链烯基(特别是C2-4链烯基)或链炔基(特别是C2-4链炔基),它们各自可被卤素,烷氧基(特别是C1-4烷氧基),环烷基(特别是C3-7环烷基,如环丙基或环己基)取代,可选择取代的芳基(特别是被卤素,C1-4烷基,C1-4卤代烷基,C1-4烷氧基或C1-4卤代烷氧基可选择取代的苯基),可选择取代的杂芳基(特别是被卤素,C1-4烷基,C1-4卤代烷基,C1-4烷氧基或C1-4卤代烷氧基可选择取代的吡啶基或嘧啶基)或氰基。
本发明的另一方面提供了通式(Ⅰ)化合物,和其衍生的酸加成盐和季铵盐和N-氧化物,
P-R2-Q
其中R1代表式(A)的基团:
其中W,X,Y和Z或代表基团CR或氮原子,条件是W,X,Y和Z中两个以下代表氮原子,且每个R各自独立地选自氢和卤原子和氰基,氨基,肼基,乙酰氨基,羟基,烷基,羟基烷基,烷氧基,卤代烷基,卤代烷氧基,链烯基,链烯氧基,烷氧基链烯基,链炔基,羧基乙酰基,烷氧基羰基,芳基和杂环基,所述基团至多含有6个碳原子,且其中R2代表二合的链基,其选自取代的或未被取代的亚烷基,亚链烯基,亚烷基芳基亚烷基,羰基和二乙酰基。R1优选为卤素-取代的苯基,吡啶基或二嗪基。
本发明的另一方面提供了式(Ⅰ)化合物其中J为-CH2-CH2-CH2-,CH=CH或CH2-CH2。
本发明的另一方面提供了式(Ⅰ)化合物,其中Ar为苯基,吡啶基。哒嗪基或吡嗪基,它们都可被卤素(特别是氟,氯或溴),C1-4烷基(特别是甲基),C1-4烷氧基(特别是甲氧基),C2-4链烯基C2-4链炔基或氰基选择性取代。
本发明的另一个方面提供了式(Ⅰ)化合物,其中R1为被卤素(特别是氯或氟),C1-4烷氧基(特别是甲氧基或乙氧基)或氰基可选择取代的苯基,或被卤素(特别是氯或氟),C1-4烷氧基(特别是甲氧基或乙氧基)或氰基可选择取代的吡啶基,哒嗪基或吡嗪基(特别是氯或溴取代的吡啶基)。
本发明的优选方面提供了式(Ⅰ)化合物及其酸加成盐,其中R1代表被卤素可选择取代的苯基或被卤素可选择取代的吡啶基,哒嗪基或吡嗪基,R2代表至多6碳原子的亚烷基或二羧基酰基。
本发明的另一个方面提供了式(Ⅰ)化合物,其中R1为被卤素(特别是氯或溴)可选择取代的吡啶基。
本发明进一步的方面提供了式(Ⅰ)化合物其中R2为至多含有8碳原子的亚烷基。
本发明特别优选的一组化合物是其中R1代表被卤素可选择取代的苯基或吡啶基和R2代表至多含有4碳原子的亚烷基,或乙二酰基的化合物。
特别优选的一组化合物是其中R1代表5-卤代吡啶-3-基和R2代表二亚甲基的化合物。
优选的R3为氰基。
优选的J为CH2-CH2或CH=CH。
根据本发明具体的式(Ⅰ)化合物包括下述表Ⅰ列出的化合物,其中R3为氰基,J为CH2-CH2,基团P和Q相同,以下给出了各化合物R1和R2代表的基团,以及其熔点(℃)。
表Ⅰ化合物序号 R1 R2 熔点
1 5-氯吡啶-3-基 乙二酰基 15-108℃
2 5-氯吡啶3基 二亚甲基 166-170℃(分解)
3 2,3-二氟苯基 二亚甲基
4 戊氟苯基 四亚甲基
5 2,3-二氯苯基 二亚甲基
6 3,5-二氟苯基 二亚甲基
7 3,5-二氟苯基 乙二酰基
8 5-氯吡啶-3-基 六亚甲基
9 5-氯吡啶-3-基 1,4-亚二甲苯基
10 5-氯吡啶-3-基 1,4-苯二羰基
11 5-氯吡啶-3-基 丙二酰基
12 5-氯吡啶-3-基 丁二酰基 253-255℃
13 5-氯吡啶-3-基 羰基 186-188℃(分解)
14 吡啶-3-基 二亚甲基
15 6-氯哒嗪-3-基 二亚甲基
16 6-氯吡啶-3-基 二亚甲基
17 6-氯吡嗪-2基 二亚甲基
18 2,6-二氯嘧啶-4-基 二亚甲基
19 5-溴吡啶-3-基 乙二酰基
20 5-乙氧吡啶-3-基 二亚甲基
21 5-溴吡啶-3-基 二亚甲基
22 5-氯吡啶-3-基 亚甲基
23 5-氯吡啶-3-基 3-亚甲基-1,2,4-噻二唑-5-基 油
式(Ⅰ)化合物的制备可采用文献中所述的方法,通过一或多种下述和实施例中进一步说明的合成技术,或通过结合文献中的方法和下述的方法而完成。在式(Ⅲ)-(Ⅶ)中的基团R4为烷基或苯基烷基(特别是苄基)。
其中的托烷氮原子连接成胺的式(Ⅰ)化合物可通过式(Ⅱ)化合物与式LR2L的化合物,在如碳酸钾的适合的碱存在下反应而制备,LR2L中,L是适合的离去基(如卤素或三氟盐)。
另一种选择是,其中的托烷氮原子连接成胺的式(Ⅰ)化合物可通过在适合的还原剂如甲酸存在下,用二醛(OHC-R5-CHO;其中R2为H2C-R5CH2)还原氨化式(Ⅱ)化合物而制备。
其中的托烷氮原子连接成酰胺的式(Ⅰ)化合物可通过用适合的碱,如氢氧化钠,在二酸氯化物ClOC-R5-COCl,其中R2为OC-R5-CO存在下处理式(Ⅱ)化合物而制备。是乙二酰二胺的式P-R2-Q的化合物由相应的式Ⅱ化合物以类似方式采用乙二酰氯制备而来。
其中R3不为氰基的式(Ⅰ)化合物可采用适合的方法制备,即或将氰基转化为所需的R3基或用所需的R3基置换氰基。
式(Ⅱ)化合物(其中R是氢的式(Ⅰ)化合物)可通过式(Ⅲ)的化合物脱保护制备,例如,(ⅰ)用氯甲酸酯(如氯甲酸乙烯酯)处理式(Ⅲ)化合物生成氨基甲酸酯,随后将形成的产品进行酸水解(例如用盐酸)或(ⅱ)在适合的高温下用氮杂二羧酸酯(如氮杂二羧酸乙酯)处理式(Ⅲ)化合物。
其中R3为氰基的式(Ⅲ)化合物可通过用适合的碱如二异丙基酰胺锂(LDA)或双(三甲基甲硅烷基)酰胺锂处理式(Ⅳ)化合物,并用化合物R1Hal,其中Hal为卤原子,与形成的产物反应而制备。
其中R3为氰基的式(Ⅳ)化合物可通过在适合的碱,如乙醇钾或叔丁醇钾存在下,用对甲苯磺酰基甲基异氰化物(也称作(4-甲苯磺酰基)甲基异氰化物)处理式(Ⅴ)化合物而制备。
另一种选择是,其中R3为氰基的式(Ⅳ)化合物,可通过用亚硫酰氯处理式(Ⅵ)化合物,得到式(Ⅶ)化合物,接着如J.Am.Chem.Soc.,(1958)80,4677所述用氰化物处理而制备。
式(Ⅴ)化合物可通过Robinson托品酮合成的相似方法而制备,(例如参见J.Chem.Soc.,(1917)111,762和有机合成(合订本4),p816)。
其中J为C2HCH2的式(Ⅴ)化合物可通过式R4NH2的胺与环庚-2,6-二烯酮(Ⅷ)反应而制备,(例如参见,Tetrahedron,(1973)155,Bull.Chem.Soc.Jpn.,(1971)44,1708和J.Org.Chem.,(1971)36,1718)。
3-氰基-9-氮杂二环[3.3.1]壬烷的制备可通过3-氰基-9-甲基-9-氮杂二环[3.3.1]壬烷的脱甲基化,例如用氯甲酸酯(如氯甲酸乙烯酯)处理随后将生成的氨基甲酸酯进行酸水解。
其中J为CH=CH的式(Ⅰ)或(Ⅱ)化合物可通过在适合的溶剂(如二甲苯),适合的温度(如回流)下加热其中J为CH2CHZ的相应的式(Ⅰ)或(Ⅱ)化合物(其中Z为适合的基团,如硫羰-4-甲苯氧基)而制备。
其中J为CH2CHZ的式(Ⅰ)或(Ⅱ)化合物(其中Z为适合的基团,如硫羰-4-甲苯氧基)可通过在适合的碱(如N,N-二甲基氨基吡啶)存在下,用适合的氯甲酸酯(如氯代硫酰甲酸4-甲苯基酯)处理其中J为CH2CH(OH)的相应的式(Ⅰ)或(Ⅱ)化合物而制备。
J为CH2CH(OH)的式(Ⅰ)或(Ⅱ)化合物可通过用酸水解相应的其中J为CH2CH(OZ’)的式(Ⅰ)或(Ⅱ)化合物而制备,其中Z’为可水解的基团(如叔丁基二甲基甲硅烷基)。
式(Ⅱ)化合物,其中J为CH2CH(OZ’),其中Z’为氢或可水解的基团(如叔丁基二甲基甲硅烷基)和R3为氰基,可通过相应的式(Ⅳ)化合物与适合的碱,如二异丙基酰胺锂(LDA)或双(三甲基甲硅烷基)酰胺锂处理式(Ⅵ)化合物,并用化合物R1Hal,其中Hal为卤原子,与形成的产物反应而制备。
式(Ⅳ)化合物,其中J为CH2CH(OZ’),其中Z’为氢或可水解的基团(如叔丁基二甲基甲硅烷基)和R3为氰基,可通过在适合碱,如叔丁醇钾存在下,用对甲苯磺酰基甲基异氰化物(也称作(4-甲苯磺酰基)甲基异氰化物)处理相应的式(Ⅴ)化合物而制备。
式(Ⅴ)化合物,其中J为CH2CH(OZ’),其中Z’为可水解的基团(如叔丁基二甲基甲硅烷基)和R3为氰基,可通过化合物Z’L,其中L为离去基与其中J为CH2CH(OH)和R3是氰基的式(Ⅴ)化合物反应而制备。
或者,其中J为CH=CH的式(Ⅰ)化合物可通过其中J为CH2CH(OH)的式(Ⅰ)化合物与适合的脱水剂,如二乙基氨基三氟化硫的脱水反应而制备。
其中J为CH2CHF的式(Ⅰ)或(Ⅱ)化合物可通过相应的其中J为CH2CH(OH)的式(Ⅰ)或(Ⅱ)化合物与,例如氟化氢和三氟化硫的氟化反应而制备。
其中J为CH2C(=O)的式(Ⅰ)或(Ⅱ)化合物可通过相应的其中J为CH2CH(OH)的式(Ⅰ)或(Ⅱ)化合物与适合的酰氯(乙二酰氯),在适合温度(如低于-50℃)下反应而制备。
其中J为CH2CF2的式(Ⅰ)或(Ⅱ)化合物可通过相应的其中J为CH2C(=O)的式(Ⅰ)或(Ⅱ)化合物与,例如二乙基氨基-三氟化硫的氟化反应而制备。
其中J为CH=CH的式(Ⅰ)或(Ⅱ)化合物可通过相应的其中J为CH2CH(OZ’),其中Z’为适合基团(如SO2CH3)的式(Ⅰ)或(Ⅱ)化合物与适合的胺(如1,8-二氮杂二环[5.4.0]十一碳-7-烯)反应而制备。
其中J为CH2CH(OZ’),其中Z’为适合的基团(如SO2CH3)的式(Ⅰ)或(Ⅱ)化合物可通过相应的其中J为CH2CH(OH)的式(Ⅰ)或(Ⅱ)化合物与适合的酰氯(如甲磺酰氯)反应而制备。
如本文下述,本发明的一个进一步方面提供了制备式(Ⅰ)化合物的方法。
本发明更进一步的方面提供了一种防治有害昆虫的方法,即在其生长地,通过向生长地或有害昆虫施用杀昆虫有效量的含有式(Ⅰ)化合物或其衍生的酸加成盐,季铵盐或N-氧化物的杀虫组合物消灭有害昆虫。
式(Ⅰ)化合物可用于杀灭和防治有害昆虫的侵染,有害昆虫如鳞翅目,双翅目,同翅目和鞘翅目(包括条叶甲(Diabrotica),即玉米根叶甲)以及其它的有害无脊椎动物,例如蜱螨类。应用本发明化合物可消灭和防治的有害昆虫和螨类包括与农业(该术语包括种植粮食和纤维产品作物),园艺和畜牧,林业,植物来源的储藏产品,如果实,谷物和木材有关的害虫,以及与传播人和动物疾病有关的害虫。式(Ⅰ)化合物可防治的有害昆虫和螨类的实例包括:桃蚜(Myzus persicae),棉蚜(Aphis gossypii),豆蚜(Aphis fabea),埃及伊蚊(Aedes aegypti),按蚊(Anopheles spp.),库蚊(Cules spp.),棉带纹红蝽(Dysdercusfasciatus),家蝇(Musca domestica),大菜粉蝶(Pierisbrassicae),小菜蛾(Plutella xylostella),蜡根猿叶甲(Phaedoncochleariae),圆红蚧(Aonidiella spp.),粉虱(Trialeurodesspp.),棉粉虱(Bemisia tabaci),德国小蠊(Blettella germanica),美洲大蠊(Periplaneta americana),东方蜚蠊(Blatta orientalis),粘虫(Spodoptera littorlis),美洲菸夜蛾(Heliothis virescens).蝗虫(Chortiocetes terminifera),叶甲(diabrotica spp.),地老虎(Agrotis spp.),玉米禾螟(Chilo partellus),稻褐飞虱(Nilaparvata lugens),黑尾叶蝉(Nephotettix cincticeps),苹果红蜘蛛(Panonychus ulmi),桔全爪螨(Panonychus citri),棉花红蜘蛛(Tetranychus urticae),朱砂叶螨(Tetranycchuscinnabarinus),桔锈螨(Phyllcoptruta oleivora),侧多食趺线螨(Polyphagotarsonemus latus)和短须螨(Brevipalpus spp.)。进一步的实例包括对公众和动物健康有害的昆虫。
为了将式(Ⅰ)化合物施用到线虫,昆虫或螨类的生长地,或受线虫,昆虫或螨侵害敏感的植物,通常将本化合物配制成组合物,组合物中除了包括式(Ⅰ)化合物外,还包括适合的惰性稀释剂或载体,和可选择地表面活性剂。组合物防治有害线虫的施用量为每公顷0.01至10kg的活性成分,优选每公顷0.1至6kg的活性成分。
由此,本发明的另一个方面提供了杀昆虫,杀螨和杀线虫组合物,其中包含杀虫,杀螨或杀线虫有效量的式(Ⅰ)化合物和适合的载体或稀释剂。
本组合物可以粉剂,可湿性粉剂,粒剂(缓慢或快速释放),浓乳剂或浓悬浮剂,液剂,乳剂,种子包衣剂,雾/或烟剂或控制释放组合物,如微胶囊粒剂或悬浮剂的形式施用于土壤,植物或种子,有害动物的生长地,或有害动物的栖息地。
粉剂是通过将活性成分与一或多种精细粉碎的固体载体和/或稀释剂混合而配制,固体载体和/或稀释剂,例如天然粘土,高岭土,叶腊石,膨润土,氧化铝,蒙脱土,白色硅藻土,白垩,硅藻土,磷酸钙,碳酸钙和碳酸镁,硫,石灰,粉状物,滑石和其它有机或无机固体载体。
颗粒剂的配制可通过将活性成分吸收于多孔的颗粒材料,例如浮石,硅镁土,漂白土,白色硅藻土,硅藻土,磨碎的玉米穗芯等中,也可加入到硬壳材料,例如砂,硅酸盐,碳酸盐,硫酸盐,磷酸盐等中。通常用于帮助活性成分浸渍,粘合或包覆固体载体的试剂包括脂肪族和芳香族石油溶剂,醇类,聚乙酸乙烯酯,聚乙烯醇,醚,酮,酯,糊精,糖和植物油。其它添加剂还包括,如乳化剂,湿润剂或分散剂。
还可使用微胶囊制剂(微胶囊悬浮剂CS)或其它控制释放制剂,特别是用于一段时间的缓慢释放,和种子处理。
或者,组合物可为用于滴灌、灌溉添加剂或喷雾的液体形式的制剂,上述制剂通常为在一或多种已知湿润剂,分散剂或乳化剂(表面活性剂)存在下的活性成分的水分散液或乳液。以水分散液或乳液形式使用的组合物通常以包含高比例活性成分的浓乳油(EC)或浓悬浮剂(SC)形式提供。浓乳油是一种均相的液体组合物,通常含有溶于基本上不挥发有机溶剂中的活性成分。浓悬浮剂一种固体活性成分在水中的细颗粒分散液。在使用时,用水稀释浓缩物并喷雾施用到被处理的地域。
对浓乳油适合的液体溶剂包括丙酮,甲基异丁基酮,环己酮,二甲苯,甲苯,氯苯,烷属烃,煤油,白油,醇类,(例如丁醇),甲基萘,三甲基苯,三氯乙烯,N-甲基-2-吡咯烷酮和四氢糠醇(THFA)。
湿润剂,分散剂和乳化剂可以是阳离子,阴离子或非离子型。适合的阳离子型试剂例如包括:季铵盐化合物,例如溴化十六烷基三甲基铵。适合的阴离子型试剂例如包括:皂类,脂肪族单酯硫酸盐,例如十二烷基硫酸钠,芳香族化合物磺酸盐,例如十二烷基苯磺酸钠,木质素磺酸或丁基萘磺酸钠、钙或铵盐,和二异丙基-和三异丙基萘磺酸钠盐的混合物。适合的非离子型试剂例如包括:环氧乙烷和脂肪醇的缩合产物,脂肪醇如油基醇或十六烷基醇,或环氧乙烷与烷基酚的缩合产物,烷基酚如辛基酚,壬基酚和辛基甲苯。其它的非离子试剂是从长链脂肪酸衍生的半酯和己糖醇苷,所述半酯与环氧乙烷的缩合产物,和卵磷脂。
上述浓缩物通常需要耐受长期储藏,且在储藏后能够用水稀释形成在足够长的时间内保持均匀的水剂,保证其可用常规的喷雾设备使用。浓缩物可含有10-85%重量的活性成分。当稀释形成水剂时,根据使用目的,水剂中可含有不同量的活性成分。
式(Ⅰ)化合物还可配制成用于种子处理的粉剂(干种子处理剂DS或水分散粉剂WS)或液剂(胶悬剂FS,种子处理液剂LS,或微胶囊悬浮剂CS)。
在应用本组合物时,可采用施用杀虫组合物的各种已知方法,例如喷粉,喷雾或颗粒剂混合,将组合物施用到有害昆虫,有害昆虫生长地,有害昆虫栖居地,或受有害昆虫侵染的生长植物上。
式(Ⅰ)化合物可以是组合物的主要活性成分或当适合时,它可与一或多种附加的活性成分混合,其它活性成分如杀虫剂,增效剂,除草剂,杀真菌剂或植物生长调节剂。包括在与式(Ⅰ)化合物混合物中的适合的附加活性成分可以是扩大本发明组合物活性谱或增加在有害昆虫生长地持效性的化合物。它们可使式(Ⅰ)化合物的活性增效或补充,例如通过增加作用速度或克服趋避性。另外,这种类型的多成分混合物可以帮助克服或预防对一种活性成分抗性的发展。根据想要的混合物的用途和所需的补充作用的类型选择具体的附加活性成分。适合的杀虫剂的实例包括下述:
a)除虫菊酯如二氯苯醚菊酯,顺式氰戊菊酯,溴氰菊酯,三氟氯氰菊酯特别是λ-三氟氯氰菊酯,联苯菊酯,甲氰菊酯,氟氯氰菊酯,七氟菊酯,对鱼安全除虫菊酯例如多来宝,天然除虫菊酯,胺菊酯,反丙烯菊酯,五氟苯菊酯,炔酮菊酯和5-苄基-3-呋喃基甲基-(E)-(1R,3S)-2,2-二甲基-3-(2-氧杂硫杂环戊-3-基烯甲基)环丙烷羧酸酯;
b)有机磷酸酯如溴丙磷,乙丙硫磷,甲基对硫磷,谷硫磷,甲基一0五九,庚虫磷,甲基乙拌磷,克线磷,久效磷,溴丙磷,三唑磷,甲胺磷,乐果,磷胺,马拉硫磷,毒死蜱,伏杀硫磷,特丁磷,线虫磷,地虫磷,甲拌磷,辛硫磷,甲基虫螨磷,乙基虫螨磷,杀螟硫磷或二嗪农;
c)氨基甲酸酯(包括芳基氨基甲酸酯)如抗蚜威,除线威,呋喃丹,呋线磷,苯虫威,涕灭威,thiofurox,丁硫克百威,噁虫威,仲丁威,残杀威或甲氨又威;
d)苯甲酰脲如杀虫隆,或定虫隆;
e)有机锡化合物如三环锡,杀螨锡,唑环锡;
f)大环内酯如齐墩螨素(avermectins或milbemycins),例如abamectin,ivermectin,和milbemycin;
g)荷尔蒙和信息素;
h)有机氯化合物六氯苯,DDT,氯丹或狄氏剂;
i)脒类,如杀虫脒或虫螨脒;
j)熏蒸剂;
k)咪蚜胺;
l)spinosad。
如果需要特殊用途的组合物,除了上述例示的主要化学类别的杀虫剂外,在混合物中还可使用具有特定用途的其它杀虫剂。例如对特定作物的选择性杀虫剂也可使用,例如在水稻上使用防治钻心虫的特定的杀虫剂如杀螟丹或噻嗪酮。可选择的用于特定昆虫种类/靶标的杀虫剂例如杀卵-幼虫剂如chlofentezine,氟螨噻,噻螨酮和三氯杀螨砜,motilicides如三氯杀螨醇或克螨特,杀螨剂如溴螨酯,乙酯杀螨醇,或生长调节剂如伏蚁腙,灭蝇胺,蒙五一五,定虫隆和氟脲杀也可被包括在组合物中。
用于组合物中适合的增效剂的实例包括胡椒基丁醚,增效散,safroxan和十二烷基咪唑。
在组合物包括的适合除草剂,杀真菌剂和植物生长调节剂将依赖于防治的靶标和所需的效果。
组合物中包括的水稻选择性除草剂的实例可以是敌稗,用于棉花的植物生长调节剂的实例是″比克″,用于水稻的杀真菌剂的实例包括灭菌素如灭菌素-S。在组合物中式(Ⅰ)化合物与其它活性成分的比例将依赖于多种因素包括靶标类型,对混合物所需的效果等。可是通常,组合物的附加的活性成分将以其通常的使用剂量使用,如果出现增效可采用较低的剂量。
下述实施例例示了本发明。实施例1-5例示了一些式(Ⅰ)化合物的制备。实施例6-13例示了根据本发明适合式(Ⅰ)化合物施用的组合物。下述用其注册商标表示的成分具有下表中的组分。
注册商标 | 组分 |
Synperonic NP8}Synperonic NP13}Synperonic OP10} | 壬基酚-环氧乙烷缩合物 |
Aromasol H | 烷基苯溶剂 |
Solvesso 200 | 惰性有机稀释剂 |
Keltrol | 多糖 |
在实施例1和2中使用的起始物是通过下述方法从托品酮制备的。
在0℃氮气氛下,以保持温度在0℃至10℃的速度,将叔丁醇钾(22.4g)按份滴加到托品酮(11.58g)和对甲苯磺酰甲基异氰化物(21.2g)的二甲氧基乙烷(240ml)和乙醇(8ml)搅拌混合物中。然后使混合物热至室温,再搅拌4小时。在室温下静置3天后,过滤混合物,用二甲氧基乙烷冲洗固体剩余物。减压下蒸发滤液并色谱分离[SiO2;二氯甲烷∶甲醇(90∶10)]得到外-3-氰基-8-甲基-8-氮杂二环[3.2.1]辛烷(9.1g)。
在-25℃氮气氛下,将外-3-氰基-8-甲基-8-氮杂二环[3.2.1]辛烷(0.5g)的四氢呋喃(3ml)溶液加入到二异丙基氨化锂溶液中[通过将正丁基锂(1.6ml的2.5M己烷溶液)加入到二异丙基胺(0.4g)的四氢呋喃(3ml)溶液中而制备]。加完在-25℃下15分钟后,在-78℃下,加入3,5-二氯吡啶(0.588g)的四氢呋喃溶液(3ml)。1小时后,使混合物热至室温并静置过夜。然后将水加入,用乙酸乙酯(x3)提取所得混合物。合并的有机相用盐水和水冲洗,干燥(MgSO4)并在减压下蒸发。色谱分离[SiO2,二氯甲烷∶甲醇(90∶10)]得到外-3-(5-氯吡啶-3-基)-内-3-氰基-8-甲基-8-氮杂二环[3.2.1]辛烷(0.249g)。
在0℃将氯甲酸乙烯基酯(2.6ml)的四氢呋喃(5ml)溶液加入外-3-(5-氯吡啶-3-基)-内-3-氰基-8-甲基-8-氮杂二环[3.2.1]辛烷(2.6g)的四氢呋喃(25ml)搅拌溶液中。使混合物热至室温1小时以上,回流2小时,然后冷却至室温。20小时后,将混合物在水和乙酸乙酯中分配,分离有机层,用水冲洗并干燥(MgSO4)。在减压下蒸发得到外-3-(5-氯吡啶-3-基)-内-3-氰基-8-(乙烯氧基羰基)-8-氮杂二环[3.2.1]辛烷(2.0g)。
将外-3-(5-氯吡啶-3-基)-内-3-氰基-8-(乙烯氧基羰基)-8-氮杂二环[3.2.1]辛烷(2.6g)溶于甲醇(50ml)中,并加入浓盐酸(7ml)。将混合物回流3小时后,在减压下蒸发混合物并用碳酸钠水溶液碱化。用乙酸乙酯提取所得混合物,并在减压下蒸发得到棕色固体。然后用己烷冲洗得到外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷(1.2g)。
实施例1
本实施例例示了8,8’-乙二酰基二(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷)(表Ⅰ的1号化合物)的制备
在室温下,将三乙胺(0.28ml),接着将乙二酰氯(0.088ml)加入外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷(0.5g)的二氯甲烷(10ml)搅拌溶液中。加入二氯甲烷2小时后,用水(x2)和盐水冲洗混合物,干燥(MgSO4)并在减压下蒸发。色谱分离[SiO2,乙酸乙酯∶己烷(90∶10)]接着再次色谱分离[SiO2;二氯甲烷∶甲醇(95∶4)]得到8,8’-乙二酰基二(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷)(0.45g)m.p.105-108℃。
实施例2
本实施例例示了1,2-二-8,8’-(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷)乙烷(表Ⅰ的2号化合物)的制备
将外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷(0.5g),1,2二溴甲烷(1.0ml)和碳酸钾(0.552g)在乙醇(5ml)中回流3小时,然后静置过夜。然后加入1,2二溴甲烷(2.0ml),混合物加热回流7小时。过滤混合物(硅藻土),剩余物用二氯甲烷冲洗。减压下蒸发合并的有机馏份并色谱分离[SiO2,二氯甲烷∶甲醇(95∶5)]得到1,2-二-8,8’-(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷)乙烷(0.315g)m.p.166-170℃(分解)。
实施例3
本实施例例示了8,8’-羰基二(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷)(表Ⅰ中化合物13)的制备
在室温下将三乙胺(0.30ml)加入外-3-(5-氯吡啶-3-基)-内--3-氰基-8-氮杂二环[3.2.1]辛烷(0.50g)的二氯甲烷(10ml)搅拌溶液中。然后加入光气(0.52ml的1.93M甲苯溶液),并使混合物静置过周末。用二氯甲烷稀释混合物,用水(x2)和盐水冲洗,干燥(MgSO4)并在减压下蒸发。色谱分离[SiO2;乙醚]得到8,8’-羰基二(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷)(0.312g)m.p.186-188℃(分解)。
实施例4
本实施例例示了8,8’-琥珀酰基二(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷)(表Ⅰ的12号化合物)的制备
将琥珀酰氯(0.25ml)加入到外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷(1.168g)的二氯甲烷(10ml)和1M碳酸钾(10ml)搅拌溶液中。5小时后,静置混合物过夜,并在饱和碳酸氢钠和二氯甲烷之间分配。分离有机层,干燥并在减压下蒸发。将乙酸乙酯加入到剩余物中,过滤混合物得到固体产物,将其在甲醇/乙酸乙酯中重结晶得到8,8’-琥珀酰基二(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷)(0.476g)m.p.253-255℃。
实施例5
本实施例例示了外-3-(5-氯吡啶-3-基)-内-3-氰基-8-((5-(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]-1,2,4-噻二唑-3-基)甲基)-8-氮杂二环[3.2.1]辛烷(表Ⅰ的23号化合物)的制备
将外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛烷(0.248g),3-氯甲基-5-氯-1,2,4-噻二唑(0.186g),碳酸钾(0.345g)和碘化钾(0.02g)在乙醇(2ml)中回流1.5小时。然后将混合物冷至室温,加入水并用二氯甲烷(x2)提取混合物。用盐水冲洗合并的提取物,干燥(MgSO4)并在减压下蒸发。色谱分离[SiO2;二氯甲烷∶甲醇(98∶2)]得到外-3-(5-氯吡啶-3-基)-内-3-氰基-8-((5-(外-3-(5-氯吡啶-3-基)-内-3-氰基-8-氮杂二环[3.2.1]辛-8-基)-1,2,4-噻二唑-3-基)甲基)-8-氮杂二环[3.2.1]辛烷(0.083g)。
实施例6
本实施例例示了一种浓乳油组合物,它容易用水稀释转化成适于喷雾目的的液体制剂。本乳油的组成如下:
%重量
化合物1 25.5
SYNPERONIC NP 13 2.5
十二烷基苯磺酸钙 2.5
AROMASOL H 70
实施例7
本实施例例示了一种可湿性粉剂组合物,它容易用水稀释转化成适于喷雾目的的液体制剂。本可湿性粉剂的组成如下:
%重量
化合物13 25.0
氧化硅 25.0
木质素磺酸钠 5.0
十二烷基硫酸钠 2.0
高岭土 43.0
实施例8
本实施例例示了一种粉剂,它可被直接施用到植物或其它表面,它包含1%重量的化合物25和99%重量的滑石。
实施例9
本实施例例示了一种与烷属烃混合后适于用超低容量技术使用的浓缩液体制剂。
%重量
化合物29 90.0
SOLVESSO 200 10.0
实施例10
本实施例例示了一种浓悬浮液胶囊剂,它容易用水稀释转化成适于液体喷雾施用的制剂。
%重量
化合物43 10.0
烷基苯溶剂(例如AROMASOL H) 5.0
甲苯二异氰酸酯 3.0
亚乙基二胺 2.0
聚乙烯醇 2.0
膨润土 1.5
多糖(例如KELTROL) 0.1
水 76.4
实施例11
一种现用颗粒剂。
%重量
化合物4 0.5
SOLVESSO 200 0.2
壬基酚乙氧化物(例如Synperonic NP8) 0.1
碳酸钙颗粒(0.3-0.7mm) 99.2
实施例12
一种胶悬剂:
%重量
化合物8 5.0
高岭土 15.0
木质素磺酸钠 3.0
壬基酚乙氧化物(例如Syperonic NP8) 1.5
丙二醇 10.0
膨润土 2.0
多糖(例如Keltrol) 0.1
杀细菌剂(例如Proxel;注册商标Proxel) 0.1
水 63.3
实施例13
本实施例例示了一种水分散颗粒剂。
%重量
化合物20 5
氧化硅 5
木质素硫酸钠 10
二辛基磺化琥珀酸钠 5
乙酸钠 10
蒙脱土粉 65
实施例14
本实施例例示了式(Ⅰ)化合物的杀虫活性。使用了许多种害虫测定式(Ⅰ)化合物的活性。除非另外指明,用含有500ppm(重量)化合物的液体组合物处理害虫。组合物的制备是将化合物溶于丙酮和乙醇(50∶50)的混合物中,用含有0.05%重量的湿润剂的水稀释溶液,直到液体组合物中含有所需浓度的化合物,湿润剂购买的“SYNPERONICNP8”牌号。“SYNPERONIC”是注册商标。
对各种害虫采用的试验方法基本上是相同的,其包括将一定数量害虫维持于通常为底物,宿主植物或害虫取食的食物的介质上,和用组合物处理介质和害虫之一或两者。然后在一段时间后,通常是处理后二至五天,评价害虫的死亡率。
以下列出了对桃蚜的试验结果。结果用死亡率等级A,B或C表示,其中C表示死亡率小于40%,B表示死亡率40-79%和A表示死亡率80-100%;“-”表示未用该化合物作试验或未获得有意义的结果。在试验中先用蚜虫侵染白菜叶,然后用供试组合物喷雾侵染叶片,3天后评价死亡率。表Ⅰ中的化合物1和2的死亡率等级是A。
化学结构式(说明书)
Claims (10)
1.式(Ⅰ)化合物,或其衍生的酸加成盐,季铵盐或N-氧化物
P-R2-Q (Ⅰ)
其中J为式-CH2-X-CH2-(其中X为亚甲基,硫或氧),X’C=CY或X’WC-CYZ(其中X’,W,Y和Z各自独立地为氢,羟基,酰氧基,烷氧基,烷基甲硅烷氧基或卤素)的二合基团;R1为可选择取代的苯基或,含有1至3个各自选自氮,氧和硫原子的杂原子的5-或6-元杂环系统,且在环中相邻原子间至少存在一个不饱和基团(双键),所述杂环可选择地被苯环稠合,其中如果存在取代基,取代基选自卤原子,氰基,烷基,链烯基,链炔基,烷氧基,卤代烷基,卤代链烯基,烷硫基和烷基氨基,上述基团至多含有六碳原子;R2为二合链基并为取代或未取代的亚烷基,亚烷芳基,亚烷杂芳基,亚链烯基,亚烷基芳基亚烷基,羰基或二酰基,条件是R2为亚链烯基或亚烷基芳基亚烷基时所述基团不具有直接键连在式(B)环氮原子上的不饱和碳原子;R3是氢,氰基,羟基烷基,烷氧基,氨基,硝基,异氰酸基,酰氨基,羟基烷基,可选择取代的杂芳基,烷氧基烷基,卤代烷基,卤代羟基烷基,芳烷氧基烷基,酰氧基烷基,偕胺肟基,磺酰基氧烷基,氨基烷基,烷氧基羰基氨基,乙酰氨基烷基,氰烷基,亚氨基,甲酰基,酰基或其羧酸或酯或酰胺,或链烯基或链炔基,所述链烯基或链炔基各自可被卤素,烷氧基,环烷基,可选择取代的芳基,可选择取代的杂芳基或氰基可选择地取代。
2.根据权利要求1的式(Ⅰ)化合物,其中R3为氰基。
3.根据权利要求1或2的式(Ⅰ)化合物,其中J为CH2-CH2或CH=CH。
4.根据权利要求1,2或3的式(Ⅰ)化合物,其中R1为卤素,C1-4烷氧基或氰基可选择取代的苯基或卤素,C1-4烷氧基或氰基可选择取代的吡啶基,哒嗪基或吡嗪基。
5.根据权利要求1,2,3或4的式(Ⅰ)化合物,其中R1为卤素可选择取代的吡啶基。
6.根据上述任一权利要求的式(Ⅰ)化合物,其中R2为至多含有8碳原子的亚烷基。
7.一种杀虫剂,杀螨剂或杀线虫组合物,其中含有杀虫,杀螨或杀线虫有效量的式(Ⅰ)化合物及其适合的载体或稀释剂。
8.在生长地消灭和防治有害昆虫,螨或线虫的方法,其中包含用有效量的权利要求1的化合物或根据权利要求7的组合物处理害虫或害虫生长地。
9.根据权利要求8的方法,其中害虫是对生长的植物有害的昆虫。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GBGB9623944.7A GB9623944D0 (en) | 1996-11-15 | 1996-11-15 | Bicyclic amine derivatives |
GB9623944.7 | 1996-11-15 |
Publications (1)
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CN1237972A true CN1237972A (zh) | 1999-12-08 |
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ID=10803098
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CN97199712A Pending CN1237972A (zh) | 1996-11-15 | 1997-10-30 | 8-氮杂二环[3.2.1]辛烷-,8-氮杂二环[3.2.1]辛-6-烯,9-氮杂二环[3.3.1]壬烷-,9-氮杂-3-氧杂二环[3.3.1]壬烷-,9-氮杂-3-硫杂二环[3,3,1]壬烷衍生物,其制备方法及其作为杀虫剂的用途 |
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US (2) | US5912254A (zh) |
EP (1) | EP0944625A1 (zh) |
JP (1) | JP2001504476A (zh) |
KR (1) | KR20000053293A (zh) |
CN (1) | CN1237972A (zh) |
AU (1) | AU4789197A (zh) |
BR (1) | BR9713041A (zh) |
CA (1) | CA2271726A1 (zh) |
GB (1) | GB9623944D0 (zh) |
ID (1) | ID22415A (zh) |
IL (1) | IL129850A0 (zh) |
TR (1) | TR199901057T2 (zh) |
WO (1) | WO1998022462A1 (zh) |
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-
1996
- 1996-11-15 GB GBGB9623944.7A patent/GB9623944D0/en active Pending
-
1997
- 1997-10-30 JP JP52330498A patent/JP2001504476A/ja active Pending
- 1997-10-30 CN CN97199712A patent/CN1237972A/zh active Pending
- 1997-10-30 EP EP97910544A patent/EP0944625A1/en not_active Withdrawn
- 1997-10-30 CA CA002271726A patent/CA2271726A1/en not_active Abandoned
- 1997-10-30 IL IL12985097A patent/IL129850A0/xx unknown
- 1997-10-30 KR KR1019990704276A patent/KR20000053293A/ko not_active Application Discontinuation
- 1997-10-30 TR TR1999/01057T patent/TR199901057T2/xx unknown
- 1997-10-30 WO PCT/GB1997/002987 patent/WO1998022462A1/en not_active Application Discontinuation
- 1997-10-30 BR BR9713041-9A patent/BR9713041A/pt not_active Application Discontinuation
- 1997-10-30 AU AU47891/97A patent/AU4789197A/en not_active Abandoned
- 1997-10-30 ID IDW990366A patent/ID22415A/id unknown
- 1997-11-13 US US08/969,635 patent/US5912254A/en not_active Expired - Fee Related
-
1999
- 1999-02-12 US US09/248,930 patent/US6066646A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ID22415A (id) | 1999-10-14 |
WO1998022462A1 (en) | 1998-05-28 |
JP2001504476A (ja) | 2001-04-03 |
CA2271726A1 (en) | 1998-05-28 |
US5912254A (en) | 1999-06-15 |
KR20000053293A (ko) | 2000-08-25 |
IL129850A0 (en) | 2000-02-29 |
EP0944625A1 (en) | 1999-09-29 |
BR9713041A (pt) | 2000-04-11 |
AU4789197A (en) | 1998-06-10 |
TR199901057T2 (zh) | 1999-07-21 |
US6066646A (en) | 2000-05-23 |
GB9623944D0 (en) | 1997-01-08 |
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